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ENCYCLOPEDIA OF EXPLOSIVES
AND
RELATED ITEMS
PATR 2700
VOLUME 2

BY

BASIL T. FEDOROFF & OLIVER E. SHEFFIELD

ASSISTED BY

EARL F. REESE & GEORGE D. CLIFT

U.S. ARMY RESEARCH AND DEVELOPMENT COMMAND

TACOM, ARDEC
WARHEADS, ENERGETICS AND COMBAT SUPPORT CENTER
PICATINNY ARSENAL
NEW JERSEY, USA
1962
 Copies of the “Encyclopedia of Explosives
And Related Items” can be obtained by requesting CD ROM
from the:

National Technical Information Service

(formerly Clearinghouse)
US Department of Commerce
Springfield, Virginia 22151

1-800-553-6847 USA only

703-605-6000
www.ntis.gov/FCPC

The contents of these volumes are UNCLASSIFIED

The distribution of these volumes is UNLIMITED

Neither the US Government nor any person acting on behalf of

the US Government assumes any liability resulting from the use or
publication of the information contained in this document or warrants
that such use or publication will be free from privately owned rights.

All rights reserved. This document, or parts thereof, may not be

reproduced in any form without written permission of the
Energetics and Warhead Division, WECAC, TACOM, ARDEC, Picatinny Arsenal

Library of Congress Catalogue Card Number: 61-61759

 I

PREFACE

This volume is a continuation of efforts to cover comprehensively the subject

matter, in the same manner & format, as in Vol I. The user is urged to read both
the PREFACE and INTRODUCTION in Vol I to understand the authors’ way of
treating the subject matter
In compiling this Encyclopedia, the authors have consulted freely with, and had
the cooperation of many individuals. Throughout this work, information received
from individuals is acknowledged in the text. A listing of others who have been
consulted or who have helped in other ways would be impractical. Mr Henry A.
Aaron son who retired from P icatinny Arsenal in 1957, after 35 years of service in
the field of propellants & explosives, contributed significant y by collecting some
references, reviewing some portions of the preliminary manuscript, and by helpful
discussions in other areas. Mr George D. Clift, formerly of P icatinny & of the
Army Chemical Center, Edgewood, Md reviewed the pencil copy, made some sug-
gestions for revision, and typed the complete copy of this manuscript. It is with
deep sorrow & sad regret that we record here the death of George D. Clift on
13 August 1962, after 45 years of experience in the field of propellants & explo-
sives
Mr L. H. Eriksen, Chief of Explosives & Propellants Laboratory, Picatinny
Arsenal reviewed the entire manuscript, and thru his interest, encouragement &
guidance this publication is possible. Special acknowledgement is due also to
other officials (both military and civilian) of P icatinny Arsenal for approving this
work and for obtaining its financial support. P icatinny Arsenal reference works
were made available thru the cooperation of all Technical Information (Library)
personnel, Mr H. Voos, Supervisory Librarian and Mr M. A. Costello, Section Chief
Although considerable effort has been made to present this information as
accurately as possible, mistakes & errors in transcription do occur. The authors
welcome the reader of this Encyclopedia to feel free to point out mistakes &
errors, so that corrections can be listed in the next volume. The interpretations
of data & opinions expressed are the responsibility of the authors and are not nec-
essarily those of P icatinny Arsenal or of the Department of the Army. This report
has been prepared for information purposes only and the Department of the Army
or P icatinny Arsenal shall not be responsible for any events or decisions arising
from the use of this information

Note: This manuscript was Varityped and prepared in camera copy pages by The
Bayshore AD-VISOR, Inc, Port Monmouth, New Jersey under Service Contract
DA-2& O17-AMC-83(A). Final corrections and/or changes in proofed copy were
made by Miss Margaret Dee thru the cooperation of Mr John P. Noonan of the
Technical Publications Unit, P icatinny Arsenal. Reproduction by photographic
offset process & binding were made by Compton Press, Inc, Morristown, New
Jersey under Service Contract DA-2& O17-AMC-235(A)
I
 III

Errata in Vol 1

Page

Abbr 9-L B Z1 = Benzyl, CGH5.CHZ- instead of CdHs .CH-

Abbr 41-R Add: propln = propulsion
propn (s) = proportion (s) instead of propulsion
Delete ps = parts per second
Abbr 46-L SC = Solventless Cordite instead of solventl ess, carbamite
Abbr 52-R TNBAc instead of TNBA for Trinitrobenzoic Acid
Abbr 52-R TNB ZN = Trinitroben zoyl Nitrate instead of Trinitro-
benzyl Nitrate
Abbr 63-R Delete WAAC = Woolwich ArsenaI
Abbr 72, 5th line from RevScInst instead of RevChimInd
the bottom
Abbr 73, 10th line from Thorpe(1940) instead of Thorpe(1949)
the bottom
“ Abbr 74, 2nd line Ullmann, VOI 4(1929) instead of vol 4(1926)
Abbr 75, 12th line from Esplosivi instead of Explosivi
the bottom
A16-L Delete DNN = Dinitronaphthol
A83-R, line 9 Formula should read: C$H~ O~(CH~CO)(C1, H2~CO), instead
of ~1-$ 03 (cH3co)(qlk120)2
A98-L, two bottom lines Replace with Action of Gas Explosions on Solid Ex-
plosives
A178-L, lines 5 & 6 Formula of Tricrotonyliden etriperoxide-tetramine should
read: H2N. R. NH. CHOR.NH. RONH2, where R is
MeCH:CH.0,.CH=
A191-R Insert at the bottom of the page the following:
Note: M. H. Werther, Rec 52, 657-77(1933) & CA 27,
5069-70(1933) describes ~ ad p-biphenyls as 2- and
4-xenylamines. He also describes prepn and props of
3,5,4’ -trinitro-2-xeny iamine (mp 2279; 3,5,4’ -trinitro
-4-xenylamine (mp 280°) and 3,5,2’,4’ -tetranitro-4
-xenyiamine (mp 2530). Their expl props were not in-
vestigated
A215-R, lines 15,16 & 17 Del ete the sentence beginning with: Aminoguanyl nitro-
saminoguanyl-tetrazene, design abed . . . . . .
A224-L, lines 8 & 9 Delete: Benzodiakole or Benzopyrazoles from the title
A224-L, line 10 Make: [59] instead of 59 and [308] instead of 308
A224-L, line 12 Indazolonimides instead of Indazolonimide
A225-L, line 10 Name should read: 1‘ -Amino- mesitylene; 1‘ -Amina-1,3,5
-trimethyl-benzene; 3,5- Dimethylbenzyl amine or
Mesitylamine,
A253-L, lines 5,6,7 & 8 Replace with: Nitroaminopropanol Nitrate, C,~N~O~ and
from the bottom Dinitroaminoprop anol, C, H, N, O,- not found in B eil or
CA thru 1956
 I

Iv

A483-L The 1ast 4 lines should read: is called AP C (armor-piercing

capped) and the cap is known as ballistic cap, This cap
is covered with a conical cup called windshield or /alse
og~ve, the purpose of which is . . . . . . . . . .
A523 Barium Diazide, mw 221.41, N 37.96%; instead of mw 243.43,
N 51.79%;
A603-R, line 14 Replace C,H, ONO with C,~ ONO,
A630-L, lines 5, 6 & 7 Delete the sentence begiming with: Azidobenzenediammo-
from the bottom niumhydroxide. See. . . . . . . and replace it with: Azido-
benzenediazonium Hydroxide. See under Benzenediazonium
Hydroxide and Derivatives
A643-L, line 21 Delete: Azidotrinitromethane. See under Methane
A676-L, Ref 21 Delete: dash (-) between P epin Lehalleur
A676L, Ref 31 A. P6rez Ara instead of A. Perez Ara
A676-R, Ref 38 Delete: comma (,) after Buenos
A678-R, 1st line Change to read: Ballistic Cap and Windshield A483-L
A678-R, lines 18 & 19 Del ete: Benzodi azole, Benzopyrazole or Aminoindazole
A224-L
A692-R, line 3 Change to read Ballistic Cap and Windshield A483-L

I
 v

TABLE OF CONTENTS

Page

Preface I

Errata inVol 1 III

List of Figures and Illustrations VI

Abbreviations, Code Names and Symbols VIII

Abbreviations for Books and Periodicals IX

Descriptive Text of Encyclopedic Items

B(Explosif) to BWC Blto B394
C(Explosifs) to Chloric Acid cltoc 210

Table I. Comparison of Brisance Values Calculated by B 266

Kast’s Formula, Relative Brisance Values Ob-
tained by Various Procedures, Detonation
Velocities and Power by Various Methods for
Principal Explosives

Table II. Comparison of Calculated Detonation Velocities B 298

with those Published in the Literature

Table III. Rifle Bullet Imp act Sensitivity of Explosives B 335

Tested in 1- or 2-inch Pipe Nipples with
Caliber .30 Ball, M2, Unless Otherwise Stated

Table IV. Rifle Bullet Impact Test by French Method B 339

Table V. US G’M and Howitzer Propellants c 34

Table VI. US Mortar and Small Arms Propellants c 33

Table VII. US Recoilless Rifle Propellants c 35

Table VIII, Thermochemical Properties of Nitrocelluloses c 104

Table 1. Original Cheddites or Street Explosives C 156

Table 2. Cheddites Used Prior to WWH c 157

Table 3. Non- gelatin

“
TvDe Chlorate
.,.
Cheddites c 157
 I

VI

TABLE OF CONTENTS

Page

Table 4. Newer Types of Chlorate Cheddites c 159

Table 5. Post WWII Perchlorate Cheddites c 159

Table IX. Types, Grain Dimensions, Weights of Charges and c 211

Other Data for Propellants Used in US Army
Artillery Ammunition

List of Books on Explosives and Propellants C 215

Index of Subjects as Alternate Names of Items C 217

I
 VII

LIST OF FIGURES AND ILLUSTRATIONS

Page

Typical Pressure-Time Record for the Blast from a Bomb B 181

Formation of “Mach Wave” and “Triple Point” B 183

Compound Blasting Cap B 186

Electric Blasting Initiators B 188

Electric Blasting Squibs B 213

Bomb Explosive Train B 223

Incendiary Bomb Cluster B 227

Methods of Stabilizing Bomb Flights B 227

Bomb, General Purpose (1000-lb) B 228

Light Case (4000-lb) B 228
Armor Piercing ( 1000-lb) B 228
Capped Armor-P iercing (1000-lb) B 228
Semi-Armor Piercing ( 1000-lb) B 228
Depth (650-lb) B 228
Fragmentation, Fin Type B 228
Practice (100-lb) B 228
Fragmentation, Parachute Type B 228
Incendiary (2-lb) B 229
Incendiary (4-lb) B 229
Leaflet (500 & 100-lb) B 229
Bread Basket B 230
US Representative Types B 231
Electron (l-kg) B 235
Butterfly (4-lb) B 239

Booster, Igniter and Detonator Units B 244

Body and Booster Assembly B 244

US Bomb Nose Fuze with Booster B 244

Italian Mechanical Impact Nose Fuze with Booster B 244

French Mortar Bomb (l-kg) with Nose Fuze and Booster B 244
1

VIII

Page

Typical Italian Booster B 245

Japanese Gaine for Skipping Bomb B 245

Japanese Army Gaines (Boosters) B 245

Typical Bullet & Cartridge Case Assembly B 328

US Caliber .45 Revolver Bullets

.22 Rifle Bullets B 328
.22 Ammunition B 328
.30 Rifle Bullets B 328
.30 Carbine Bullets B 330
.50 Bullets B 330

French Bullet Test B 338

Apparatus for Calibration of TNT Thermometers C6

TNT Setting Point Determination by Cup Method C7

Apparatus for Determination of Camphor c 21

Cannon Propellant Grains c 30

Rocket Propellant Grains c 30

Multiperforated propellant Grain c 31

US Cannon Propellants c 31

US 12-Gauge Shotgun Cartridge c 73

Types of US Cartridge Cases c 74

Components of Typical US Small-Arms Cartridges c 74

Grenade Cartridges c 75

Caliber .30 Carbine Cartridges c 75

Caliber .45 Cartridges c 75

US Complete Rounds of Artillery Ammunition c 75

Cartridge, HE for 75 mm Recoilless Gun c 75

Charge, PropeHinG M3, M4A1 & M13 c 77

 lx

SUPPLEMENT TO ABBREVIATIONS, CODE NAMES AND SYMBOLS

GIVEN INVOL l, PpAbbrlto65

acct account LASER Light Amplification by

Simulated Emission of
AMC Army Materiel Command,
Radiation
formerly OCO, Washington
25, D.C. MASER Micro wave Amplification by
Simulated Emission of
Radiation
BDSD Base-detonating self- MeCentr MethyI CentraIite
destroying (fuze) milit military
Bzl B enzyl, ~H~ .CHZ- instead
of ~H5 .CH-, which was Oc Open Cup (for detg flash point)
given in Vol 1, p Abbr 9 OEHO Ordnance Engineering Handbook
Office (Duke Univ, Durham, NC)
capy capacity ORDP Ordnance Pamphlet
cc Closed Cup (for detg flash
point) PEPA Projectile emp enn~ & propulsion
Centr 1 N,N’ -Diethylcarbanilide or additionnelle ( Fr for Finned
EtCentr Projectile with Additional
Centr 2 N,N’ -Dimethylcarbanilide or Propulsion)
MeCentr
Centr 3 N-Ethyl-N’ -methyl-carbanilide MA mixed acid (sulfuric & nitric
Centr 4 N-Methyl-N’ -toIy)-carbanilide acids)
MUCOM Munitions Command, formerly
CPCEM Comp agnie de produits
OSWAC, Dover, N.J.
chimiques et dlectrom~tal-
Iurgiques, Alais, Froges & Program Evaluation Review
PERT
Cam argue
Techniques
P WP Plasticized with white
descr (d) describe(d) phosphorus
destruc destructive
SACMS Scientific Advisory Council of
destrucn destruction
Mini stty of SuppIies (GtBritain)
DEt Ph Diethylphthalate Sc SolventIess Cordite, in lieu of
DPhU Diphenylurea Solventless Centrality given in
Vol 1, p Abbr 46

EAM Electric accounting machine TCC Tag Closed Cup (for detg flash
Egor eg Example or for example point)
elevtd elevated TNBAc Trinitrobenzoic Acid in lieu of
EtCentr Ethyl Centrality TNBA given in Vol 1, p Abbr 52
extrml y extremely TNBzN Trinitroben zmyl Nitrate in lieu
of Trinitroben zyl Nitrate given
flamy fl amiability in Vol 1, p Abbr 52
fractn fraction TNphlGl Trinitrophloroglucinol
fractnl fractional TOC Tag Open Cup (for detg f 1ash
point)
hydrcar(s) hydrocarbon(s)
WADC Wright Air Development Center,
insens insensitive changed to WADD
insensy ins en sitivit y WADD Wright Air Development Division,
formerly WADC
I
 XI
SUPPLEMENT TO THE
LIST OF ABBREVIATIONS FOR BOOKS AND PERIODICALS
GiVEN IN VOL 1, pp Abbr 66 to Abbr 76

ADL Punch Cards, Arthur D. Little Inc, “Punch Card Recording of Data on
Vol (1961) Explosives, ” Cambridge, Mass, Vols 1,3 &4(1961 (U) and
Vol 2 ( 1961) (C)
ADL PureExplCompds Arthur D. Little, Inc, ‘ ‘Report on Study of Pure Explosive
(Part & Year) Compounds, ” Cambridge, Mass, P art 1(1947> Part 2(1947)
Part 3(1950) & Part 4(1952)
ADL, SynthesisHE’s Arthur D. LittIe, Inc,
“Synthesis and Testing of High
(Rept & Year) (C) Explosives, ” Cambridge, Mass, 1st Report( 1949), 2nd
Rept(1951), 3rd Rept(1953) & 4th Rept(1956)(Conf)

AFCJ Armed Forces Chemical Journal, Washington 6, DC

Blasters ‘Hdb(1952) instead of Blaster’s Hdb(1952) of Vol 1, p Abbr 67

Corner, Ballistics(1950) J. Corner, “Theory of Internal Ballistics of Guns, ” Wiley,
NY(1950)
DictGuidedMissile s(1959) G. MerriIl, Edit, “Dictionary of Guided Missiles and Space
Flight, ” VanNostrand, NY(1959)

Ellern, Pyrotechnics 1961) H. Ellern, “Modern Pyrotechnics” ChemPublgCo, NY(1961)

Encyclopedia 1(1963) B .T. Fedoroff et al, “Encyclopedia of Explosives and

Related Items, ” PATR 2700(PB No 171603), Dover, NJ(1960)

Faber, Pyrotechnics H. B. Faber, “Milit aty Pyrotechnics, ” USGovtP tgOff,

(Vol & Year) Washington 25, DC, VOIS 1,2 R 3(1919)

Farrow’s MilitatyEncycl E. S. Farrow, “Military Encyclopedia, ” Military-Naval Pd>g

(1895) Co, NY, Vols 1-3(1895)

Feigl (Vol & Year) F. Feigl, “Spot Tests, ” Elsevier, Amsterdam, Vol 1
(Inorgmic)( 1954) and 2 (@ganicX1956)
Gardner’s ChemSynonyms W. Gardner & E.I. Cooke, C‘Chemical Synonyms and Trade
Names, ” VanNostrand, NY(1948)
Giua, Trattato 6 (1959) M.Giua et al, “Trattato di Chimica Industrial,” UTET,
Torino, Vol 6( 1959)

Glossary of 0rd(1959) W. H. Holler, Edit, “Glossary of Ordnance Terms, ” OEHO,

Duke Univ, Durham, N. Carolina(1959)
GreatChemists(1961) E. Farber, Edit, “Great Chemists, ” Interscience, NY( 1961)
Greener(1881) W. W. Greener, “The Gun and Its Development, ” Cassell,
Petter & Co, London(1881)
Jacob son(Vol & Year) C. J acob son, “Encyclopedia of Chemical Reaction s,”
Reinhold, NY, Vol 1 (1946), 2(1948), 3(1949), 4(195 1), 5
(1953), 6(1956), 7(1958) & 8(1959)

Macmillan’s Encycl (Vol & Year) “The Macmillan Everyman’s Encyclopedia,”” Macmillan,
NY, Vol 1 (1959)
Marshall, Dict( 1920) A. Marshall, “Dictionary of Explosive S,” Chuchill, London
(1920)
 XII

Mellor(1961) “Mellor’s Modern Inorganic Chemistry, “ Revised and

edited by G.D. P arkes, Longmans, Green& Co, London(1961)

0rdTechTerm(1962) Anon, “Ordnance Technical Terminology, ” Special Test

ST 9-152, Aberdeen Proving Ground, Md(1962) [Replaces
Glossary of Ord (1959)]

RevSciInst instead of RevChimInd in Vol 1, p Abbr 72 of Encyclopedia a

RocketEncycl(1959) J. W. Herrick, E. Burgess & W. Lanford, “Rocket Encyclo-
pedia Illustrated, ” AeroPublishers, LosAngles, CaIif(1959)
SACMS,Ballistic.s( 1951) Scientific Advisory Council of Mini arty of Supplies (Great
Britain), F.R. H. Hunt, Chairman, “Internal B alli sties, ”
Philosophical Library, NY(1951)

Snell & Snell (Vol & Year) F. D. Snell & C. T. Snell, “Calorimetric Methods of Analysis, ”
Van Nostrand, NY, VO1 1(1948), 11(1949), 111(1953) & IV
(1954) and Supplementary VOIS 11A(1959) & IIIA(1961)
Taylor (195Z) J. Taylor, ‘ ‘Detonation in Condensed Explosives, ”
Clarendon Press, 0xford(1952)
Taylor (1959) J. Taylor, “solid Propellant and Exothermic Compositions, ”
Interscience, NY(1959)
VanNostrand’s Encycl Van Nostrand’s Scientific Encyclopedia, VanNostrand, NY,
(1958) 3rd edit(1958)

Vogel, Inorg Analysis(1961) A. I. Vogel, ‘CA Textbook of Quantitative Inorganic Analysis, ”

Longmar,s, Green& Co, London(1961)

Weingart, Pyrotechnics 1947) G. W. Weingart, “Pyrotechnics, “ ChemPubIgCo,

Brooklyn( 1947)

Welcher(Vol & Year) F. J. Welcher, “Organic Analytical Reagent s,” Van Nostrand,
NY, Vol 1 (1947); 2 (1947); 3(1947) and 4(1948)

Wimpress,Ballistics P. N. Wimpress, “Internal Ballistics of Solid Fuel Rockets, ”

(1950) McGraw-Hill, NY(1950)
 ENCYCLOPEDIA of EXPLOSIVES and RELATED ITEMS

Volume 2

B(ExpIosif) An expl manufd for some time by b) BqPoudre B a canon de canpagne). Powder
Berg?s, Corbin & Co, neat Grenoble, France: B for a field gun(Ref 6, p601 & Ref 7). It is no
Amm perchlorate 89 & NG 11% longer in use
Re/: Commission des Substances Explosives, c)BCNL(Poudre B ~ canon, nitratte, Iav.+e )( Pow-
MP 12, 18(1903-1904) der B for cannon, with nitrate, leached). It
was prepd by mixing 80 parts of NC gel with
B(Poudre), aIso called Poudre blancbe :or 20 ps of powdered” K nitrate, followed by grain-
Poudre ~ solvant (Formerly called Poudre V). ing and drying. Then most K nitrate was leach-
A smokeless NC propellant (poudre saris ed with water. This treatment gave(after drying)
fum~e) developed ca 1884 by Paul Vieille and a porous proplnt which was fast burning. It was
named after the first letter of Boulanger, who used for short range mountain cannons and for
was General and Minister of War at that time. blank fire(Ref 4,P228)
As the proplnt proved to be very suitable for d) BD(Poudre B 5 diph6nylamine). Powder B
rifled firearms, it was adopted by the French contg DPhA as stabilizer (Ref 2 & Ref 10, P308)
Govt for use in the LebeI rifle. It was also e)BF(Poudre B ~ fusil). Powder B for rifle.
adopted for use in field guns. Slightly earlier According to Vieille, this proplnt was less e-
and independently of Vieille, a similar proplnt rosive than either .Cordite or Ballistite (Ref 2,
was deveIoped in Germany by Max von p295 & Ref 10,p388)
Duttenhofer and designated RCP (Rottweiler f)BFNL(Poudre B ~ fusil, nitrat6e 1av6e). POW-
Cellulose Pulver) (Refs 1,2,3,10,11,13,14,16 der B for rifle with nitrate, leached. A porous,
& 17) rapid-burning proplnt prepd in the same man-
The original poudre B consisted of small, flat ner as BCNL{see item b)(Ref 4, P228)
squares, pale yel or brownish in CO1, and having g)BFP(Poudre B en pailletes pour fusil de
an odor of ethyI acetate, which was used as guerre). Designation for a rifle propInt in the
a solvent for NC. Its approx compn was CP, form of leaflets, contg camphor and centrality
(coton-poudre n“l) (NC with 12.9 to 13.4%N; (Ref 5,p282)
insol in eth+ ale) 68.2, CP2(coton-poudre n02) h)BFP, (Poudre B en paillettes pour fusil de
(NC with 11.7 to 12.2$%A; SOI in eth-ale) 29,8 guerre). Powder B in the form of leaflets for
& paraffin 2% (Refs 1 & 2). The above form- use in military rifles. It contained some cam-
ulation was modified severaI times and the phor(Ref 5,p282)
resulting proplnts were known as #roudres BN i)BG(Poudre B de guerre destin~e a I’arm&e de
where N stands for ‘nouvelle’, meaning new terre). Powder B, military, destined for the
(Ref 2). One such proplnt contained CP, 40, Army. This proplnt was designated BG1, BGZ,
CP2 30, Ba nitrate 18, K nitrate 8, Na carbon- BG3, BG4 etc depending on the caliber of the
ate (or tannin) 2, residual solvent 1 & moist gun in which it was used. For instance, BG4
1% (Refs 7 & 9) was used in the 120mm gun. It was made in
In about 1890 all the ingredients, except NC the form of strips, 1.45mm thick and 18mrn wide
and a solvent, were discarded and then/later (Ref 6, P601). The higher the index, the slower
(in 1896-7) some amyl alcohol was incorporated is the propeH*t(Ref 15,p458)
to serve as a stabilizer. These proplnts were j)BGC(Poudre B de guerre pout gros calibre).
designated as B(AM) or BAm (see VO1 1 of this Powder B for use in large caliber guns(Ref 2,
Encyclopedia p A395-L). As amyl alc proved to p297)
be unsatisfactory it was replaced with a srnall k)BM(Poudre B de marine). Powder B, Navy.
amt(O.5-2%) of DPhA. This is a satisfactory This proplnt has been designated as BM1,
stabilizer which is still in use(Ref 2 & Ref 14, BMZ . . . . . . .to BM20, where the indites indicate
P249) the approx caliber of the gun for which the pro-
Poudres ~ existed in the following varieties: pellant is intended. F~r instance, the BM7 was
a)B(Am). See above intended for use in the caliber 7 gun, such as
 I

B2

155mm(Ref 6, & Ref 10,326) B4 or Type 2 Explosives. Lt grey powdery

l)BN(Poudre B nouvelle). See above mixts of TNAns 60 or 70 with Al 40 or 30%
m)BAJF(Poudre B nouvelle, pour fusil). Powder used i n Japanese i n cendimy submarin e gun
B, new, for rifIe(Ref 7) shel 1 s. The props o f the 60/40 m ixt we~e:dl.90
n)BN3 F(Poudre B ~ fusil nitrat=e, pour expor- (cast), power by ballistic pendulum 64%(PA=
tation). Powder B for rifle, nitrate treated, for 100%), brisance by copper cylinder crusher 82%
export(Ref 4,p226) (PA= 100%), explosion point 300 to 505°, impact
O)BN 3 F. A clurent proplnt designed for use sensitivity with 5-kg wt 17cm(max for no explns)
in smooth-bore hand weapons(Ref 14,p252) and /riction sensitivity 60kg(ma x pressure be-
p)BiVLM. C)ne of the older poudres B for small tween two rubbing surfaces)
arms. It was quick-burning(Ref 5,p294) Re/: R. A. Cooley et al, ‘Japanese Explosives’,
q)BZZU. C)lder poudres B stabilized with urea PB Rept 53,048(1945)
(Ref 5,p296) B77. A kind of black powder used in the Rus-
r)BS(Poudre B succ~dann6e de la poudre noire sian artillery from 1877 up to the adoption of
SP pour Ie canon de si~ge et de place). Pow- smokeless propellant Pyrocollodion(N= 12 .44%)
der B replacing black powder SP, for use in developed by Mende16ev ca 1891
siege and fortress guns. It was also used during Refi Dr M. M. Kostevitch, Buenos A ire S, Argen-
WW1 in 75mm guns(Refs 2a & 6) tina; private communication(1955)
t)BW. According to Mangini(Ref 11a), poudre
BW consisted of CP, 40, CP2 30, K and Ba BA- 107. Polybutadiene-Acry lic Acid Corn posite
nitrates 26, Na carbonate 2 & volatiIes 2%. Propellant for Rocket Motors developed by
Mangini(Ref 11a) also gives the compn of poudre Thiokol Chemical Corp. Its compn and props
B as follows: CP, 50-75, C P2 50-25 & DPhA are given in conf ‘Propellant Manual’ ,SPIA/h12
(added) 0.5%. A mixt of ether & alcohol is used (1959), Unit No 572 B(AM) or BAm(poudre).
as a gelatinize See Vol l,pA395-L
Stettbacher(Ref 12) gives for the current poudre
B: NC(13 to 13.4%N) 80 & NC(ll.7 to 12.2%N) Bachmonn,Werner E (1901-1951). An Am er chem-
20% with 1.5 to 2% of DPhA added, all blended ist specializing in org synthesis. During WWII
with eth-alc as a gelatinize he developed for OSRD a new, efficient pro-
Method of manufg poudre B as practiced before cess for manufg cyclonite(R13X)
TW1l is described in: Ref 4,pp228-233; R.ef 6, Refi A. L. Wilds, JOC 19,129-30 (1954 )( Obituary)
pp 580-601; Ref 9, pp 292-310 & Ref 15,p 458
Re/.s: l)Daniel(1902), 50 2)Marshalll(1917 ),294-7 Backblast. Rearward blast of gases to the rear
2a)Chevereau,MP 19,168(1922) 3) Brunswig, of recoilless weapons, rocket launchers and
ProK1926},7 & 134 4)Pascal(1930),226 & 228-36 rocket-assisted takeoff units
5)Desmaroux,h!P24,282 & 294-6(1930-1931) Re/: Glossary of 0rd(1959),28
6)Vennin, Burlot & L 6corch6(1932),578-602)
7)Marshalf 3(1932),85 8)Stettbaci@ 1933),190 & Backbreak, When blasting hard rocks by sev-
197 9)Pepin Lehalleur(1935),289-90 9a) p. eral charges placed in boreholes, it is very
Vieille$iP27,7- 10(1937 )(History of ‘poudre V‘, important that the charges are fired in rotation,
now known as ‘poudre B ‘), 10)Davis(1943),258, in pairs, in the proper sequence. If this order
292-4,308,326 & 388 ll)P6rez Ara(1945),438-9 is not followed, poor breakage will restdt. Such
&44 1 lla)Mangini,Explosive( 1947),235 121Stett- improperly fired charges cause what is known
bacner( 1948),41 13)Vivas,Feigenspan & Ladreda as backheak. In order to ackieve the proper
R, 294s),96 14)P. Tavernier,MP 32,244 & 250( 1950) rotationa~ firing, deIay caps are usually em-
: 5)J .Fauveau,MP 33,458 & 463( 1951 ) 16)Stettbacher, ployed. More precise timing is obtained by
P6ivoras(1952),51 17)C.Belgrano,’Gli Explosive’, using the so-c ailed DuPont Blasting Timer
I-ioepli,Milano( 1952),109-10 Refs: l)Blaster’s Hdb(1949),15 & 99 2)Blaster’s
Hdb(1952),lll & 241
B(Value). See Brisance Value of K ast
Backflash, or (Backfire, Breechflash or Flared
B4. A Ger vehicle contg a demolition charge.
It was used during WWII for destruction of back). The flash produced at the breech of a
enemy targets, such as bridges, pillboxes, etc. gun when the breech is opened after firing a
For more info, see PATR 2510( 1958),p Ger 11 round. This is caused by the ignition (and

.
 83

expln) of CO and hydrogen of combustion early as 1896, when Bokorny(Ref 1 ) stated

gases at the moment of their contact with that NC is utilized by both bacteria and fungi
oxygen of the air. If the temp of the gases is (such as encountered in contaminated wateri as
not sufficiently high to produce self-ignition, a source of carbohydrates and nitrogen. In his
the back-flash may be caused by a piece of experiments a highly esterified N C was broken
smoldering or burning resi due of proplnt or bag down in water contg bacteria & fungi together
left in the gun barrel after firing. with small quantities of mineral substances
The presence of CO and hydrogen is ex- needed by micro-organism. No decompn of NC
plained by the incomplete combustion of the took place, however, when experiments were
proplnt which is required in order to keep the conducted in distilled w. Malenkovic(Refs 2 &
temp in the barreI sufficiently low to avoid ex- 3) stated that neither NC nor NG is directly
cessive barrel erosion. This is achieved by not decompd by mold” but if one or both of them are
allowing sufficient oxygen for complete com- stored incontact with substances attacked by
bustion(to produce C02 and H ~o) in the form - mold(such as paper), they are also decompd.
uIation of the proplnt and by incorporating in The same investigator claimed that NG alone is
the proplnt some cooling(flash-re ducing) agents definitely a mold poison, but he was not sure
Precautions must be taken to prevent the about NC. Jacqu6(Ref 4) stated that water used
flareback from reaching the new proplnt charge, for washing NC is the principal source of bac-
as well as to prevent burns to the gun perscm- teria which causes deterioration of NC. He
eI. Certain guns are equipped with com pressed found that micro-organisms do not live in dry
air gas ejectors which expel the gases in the NC but thrive in moist material. One of his
bore before the breech opened. Even when so e- findings was that compressed guncotton with
quipped, it is essential that the bore be ins pett- 15% moisture was infected with reddish or
ed for burn ing residue b efor e the next round is greenish bacteria without, however, appreciable
inserted. If the gun is not equipped with a gas changes of NC in weight, N content, or stability.
ejector, the new propelling charge must not NG and NG-expls(such as dynamites) did not
be brought near the breech until a wet chamber support org life and attempts to inoculate such
swab has been used. Guns with muzzle brakes media failed. Some algae and aquatic plants
and semi-automatic closures tend strongly to- yielded decompn products(such as oxalic acid,
wards breech-flashing etc) which caused decompn in nitric esters
Back-flash is practicably negligible with under the action of heat. Fabel(Ref 5) also
small caliber guns (with fixed ammo) but can pointed out that NC can serve as a source of
be very serious with large guns. (See also nourishment for bacteria. Kaye(Ref 6) studied
‘Muzzle Flash’) Note: According to Stickland at PicArsn, by means of an electron micro-
(Ref 4), the only reliable meams of fighting the scope, the action of micro-organisms on grains
breech (and muzzle) flash is the use of a cool of the propellant M8, stored for some time in a
proplnt, such as Gudol, described in PAT R, magazine. The compn of M8 WaS: NC(N= 13.25%)
2510( 1958),Ger 81 52.15 tl.50, NG 43.00 t1.50, DEtPh 3.00t0.50,
R e/s: l)hlatsha H 1(1917), 318 2)Marshall 3 K nitrate 1.25*0.25 & Et Centr 0.60+0.20%.
(1932),93 3)Hayes(l 938) ,35-6 4)0. W. Stickland It was found that surfaces of grains of proplnt
PB Rept 925(1945),83 5)Glossary of 0rd(1959), exhibited contamination by micro-organisms
28,49 & 119 which ranged in shape from spheres and cylin-
ders to rods and squares. Penetration of these
Bacan,Roger (1214 ?-1292). An English alche- bacteria beyond the surface was also apparent.
mist, considered to be one of the inventors of The contamination probably re suited from bac-
a compn similar to black powder. blade numerous teria encountered in water used during manuf
other contributions in various branches of of M8 by the slurry method
science R e/s: l)T.Bokorny, ChemZtg 20,985-6(1896)
Ref: F. J. Moore, ‘A History of Chemistry’, 2) B. Malenkovic,MitteilGegenst~*de-Artil-Genie-
McGraw-HiIl,NY( 1939),25 wesen 1907,599-615 & CA 1,2411(1907) 3)B.
Malenkovic,Revue d’Artillerie 1908,261( 1908) &
Bacteria and Mold Action on Nitric Esters and CA 3,248(1909) 4)M.Jacqu~ SS5,81-2(191O) & CA
on Smokeless Propellants. Influence of micro- 4,1546( 191O) 5)K.Fabel,$*Nitrocellulose’’,F.Enke
organisms upon stability of NC was studied as Verlag,Stuttgart( 1950),pp 115-6 (Verhalten gegen
 B4

Bakteria und Pilze) 6)S.M.Kaye,PATR 2210(1955) tics and Chemicals’, Technological Rept Series
(An electron Microscope Examination of the Sur- No 8,Sugar Research Foundation,Inc,NY( 1952),
faces of M8 Pro~ellant) 202pp

Bacteriological or Biological Warfare. See under Bagasse Pith is the loose spongy tissue occu-
Chemical, Biological and Radiological (CBR) pying the center of the sugar cane. It has been
Warfare used in expIs(Ref 2). Cbapman(Ref 1 ) patented
its use with NC-NG mixts to make low density
Badische Aniline-und A Ger-
Sodafabrik(BASF). gelatin-dynamites
man concern, one of the biggest in the world. Re/s: 1 )F.F.Chapman,USP 19921 89(1935) & CA
It formerly manufd various chemicals, includ- 29,2745(1935) 2)Bebie(1943),30
ing some explosives. Its history is described
in the booklet entitled: ~BASF schreibt Ges- Bags for Propelling Charges. See Cartridge
chichte’,Ludwigsh aven(1952),29pp Bags

Baelinites. Mining expls contg AN 85-95 & Baka(Suicide) Bomb or Kamikaze(The name Baka,
TNT 15-5%(Refs 1 & 2). According to Ref 3, the meaning stupid, was given by Americans). It
baelinite contg AN 93 & TNT 7% was safe a- was a piloted rocket-propelled bomb used by
gainst firedamp the Japanese Navy during WWIL It could be
Refs: l)Gody(1907),712 2)Colver(1918),249 launched from any twin-engined p~ane at a dis-
3)Pepin LehaHeur(1935),352 tance of 20-30 miles from the target. Its over-all
length was 19 C10*, wing spread of 16c5~, wt
Bagasse is the dried crushed sugar cane resi- 4000, inclusive of a 2645-lb warhead in the
due from which the sweet juice has been ex- nose. It had a down-speed of around 550 mph.
tracted. When obtained from sugar cane the crude Its warhead was filled with 1135 lb of TNAns
bagasse contains ca 88% water. The dried ma- (Type 91 Explosive). The proplnt (6 sticks)
terial consists of ca 50% cell.uIose, 25% [ignin consisted of: NC 59.9, NG 26.9, MNN 6.1, Et
and 25% of pentosans, hemicellulose, gums and centr 2.9 & volatiles 1.3%
non-sugars. The cellulosic portion is principally Refs: l)Anon,Army Ordn 29,382(1945) & CA 30,
alpha-celIuIose with a fiber length of ca 3 .smm 116(1946) 2)Anon, ‘Japanese Explosive Ord-
and is readily isolated by the alkali or sulfate nance’, TM 9*1985.4, Washington,DC(1953 ),l16-
processes used for manufg woodpulp. Bagasse 18 3)Meriam-Webster’s (1961),1231
represents an excellent source of readily avail-
able cellulose for chemical processing and can Baked Powder(Anhydrous Powder) was prepd ca
be used in the manuf of cellulose derivs in- 1873 by the Russian Colonel Wiener by press-
cluding NC. In the powdered form it can be used ing the ingredients of black powder at 120°.
as a fuel and absorbent in dynamites By this method a more homogeneous and compact
Dry distn of bagasse produces acetic acid mass was obtained than in ordinary BkPdr be-
and methanol, leaving charcoal as a residue cause the sulfur melted and was distributed
Re/s: I)L.W.Babcock, USP 1741146(1929) & more uniformI y betw the K nitrate and charcoai.
CA 24,1220(1930) (Bagasse together with NG & As this method of manuf was dangerous it was
AN in dynamites) 2)E .I.duPont de Nemours,Brit- abandoned in 1878
P 375824(1930) & CA 27,3335( 1933) (Bagasse Re/:Daniel(l 902),808
for use as an absorbent for NG or similar Iiq
expls) 3)J.de la Roza,Sr,Mem 14th ConfAnual, Bakelite. A synthetic resin obtained by the
AsocTecAzucar,Cuba 194,331-2 & CA 3S, condensation of formaldehyde with phenols.
5317(1941) (Prepn of product contg 9~0 of alpha- Used as a plastic in many industrie s(Ref 2).
cellulose by special treatment of sugar bagasse; Was patented by the Italian Co for making
this cellulose is more easily nitrated, washed bodies of projectile :fuzes(Ref 1)
and dehydrated that linters) 4)Kirk & Othmer Re/s: 1).SocItalPolveriEspIodenti,BritP 298948
2,(1948),271 -3( Bagasse) 5)L.F.Wiggins,Chem & (1927) &CA 23,3102(1929) 2)Kirk & Othmer 10
Ind 1949,555-6 (Bagasse as a raw material for (1953),801
chemical industry) 6)C.J .West, ‘The Utilization
of Sugar Cane Bagasse for Paper, Board,P las- Bakewell & Hurst patented in 1896 & 1897 a

1
 B5

method of loading projectiles with NG and then BalIistic Cap. A forged steeI cap used on armor
freezing it in order to render it insensitive during -piercing projectiles to protect the point from
transportation and firing. Inside such project shattering upon impact with target, such as
was placed a special device which melted the steel plate. By creating an initiai stress in the
NG during the flight thus rendering it again sen- plate at impact and having a greater bite at
sitive just before bursting. These projects were angles of obliquity, it lessens possible ricochet
dangerous to handle because NG sometimes ex- and permits better complete penetration by the
ploded from shock or friction projectile(Ref 2). Various types of ballistic
Re/:Daniel(l 902),50-1 caps used in US artillery are shown on Figs 1,
2,6,etc of Ref 1. The ballistic cap is usually
Bakufun (Exploding Powder). A Jap mixt of MF, ~ covered with a UkuLdield(qv) (See also Vol 1,
K chlorate & Sb sulfide used during WWH m pA483-L under Armor-Piercing Projectile)
some initiators Refs: Anon, ‘Artillery Ammunition’, TM 9-1901
Re/: OpNav~-3M(1945),25 (1950 ),5,8 & 12 2)A.B.Schilling, PicArsn; pri-
vate communication 1960)
Bakuhats-ei (Jap). Blasting Gelatin
Ballistic Homogeneity of Poudres B was dis-
Balanced Dope, See under Dope cussed by J. Fauveau,MP 33,461-2(1951). If
samples of proplnt taken from any part of a
Balistita (Span). Ballistite lot possess identical ballistic properties, the
ballistic homogeneity is considered to be
Balistite (Fr &, Ital). Ballistite satisfactory

Ball and Disk Machine. See under Impact Ballistic Measuring Methods and Ballistic
Tests Tests. In order to determine the suitability for
military purposes of propellants, explosives,
Ball Drop Test. See Vol l,pA573-L projectiles, weapons, etc, it is required that
tests be conducted, using appropriate devices.
Bane (Fr). Bullet; ball As a final test, firings are conducted on a full
scale at proving grounds
Bane de fusil (Fr). Rifle bullet For instance, a proplnt to be ballistically
suited for a certain weapon, must provide a
Balle perfaronte (Fr). AP bullet prescribed mu~zle veloci~(qv) at a prep
sure below a prescribed maximum, which has
Bane traceuse (Fr). Tracer bullet been previously detd as safe for the weapon in
question. In order to test the suitability of a
BalI Grain Powder. See Ball Powder proplnt, a series of rounds is fired beginning
with small proplnt chges. These are increased
Ballista or Balista. A device first used by the gradu~ly untiI a muzzle velocity is reached
Remans and then by the Greeks, as early as the which is equal to or S1 higher than that desired,
1st century AD, for hurling very heavy missiles or until the max press is exceeded. During the
(Such as stones, beams, etc) against fortifica- test, samples of ?3tandar~’ proplnt are also
tions, buildings, etc. The motive power was fired alternately with the test proplnt for the
supplied by tightly twisted hemp, sinews of purpose of calibration. Pressures and muzzle
animals or raw hide. There were two types of velocities for the test proplnt are plotted as
ballistas: one throwing m i ssiles at high tra- functions of the wt of the chge. The chge
jectories from the end of a rotating arm (See (optimum charge weight) which will give the
illustration in Ref. 1, p8), the other working on desired muzzle velocity is detd from the result-
the same principle as a large catapult (See Fig ant curve. A series of uniformity tests, using the
1 in Ref 3) optimum charge weight, is then run during which
Re/s:l )Greener( 1881 ),8 2)Farrow’s Milit Encycl the variations of velocity and mean pressure
l(1895),12g 3)EncyclBritannica 5(1952),24(under must fall within narrow prescribed limits if the
Catapult) & 8 )(195~53(uder Engines of War) proplnt is to be accepted(Ref 2)@ee also under
4)Macmilla’sEncycl 1(19-7 Muzzle Velocity Determination: Pressure Meas-
 I

B6

urements, and Terminal Velocity Determinations) sile’, Doubleday,Garden Ciry,NY(1958) 5)H.E.

These tests, when conducted in different Newell, ‘Guide to Rockets, Missiles and Sat-
weapons, may also serve as ballistic tests of ellites’ ,Whittlesey House,NY( 1958) 6)R.B.Dow,
the weapons ‘Fundamentals of Advanced Missiles’, Wiley,NY
As examples of ballistic tests for explosives (1958) 7)J.W.Herrick,Ed,’Rocket Encyclopedia
may be cited brisance, power, velocity of det- Illustrated’,Aero Publishers, Inc,Los Angeles
onation tests, etc. Some of these tests are 26, Calif(1959) 8)C.E.Davis, ‘The Book of Mis-
briefly described under Physical Tests, Vol 1, siles’,Dodd,Mead & C0,NY(1959) 9)Editors of
p VIIff, of this Encyclopedia, others will be Air Force Magazine, ‘Space Weapons; A Hand-
described later. Ballistic tests for shells, book of Military Astronautics’, Praeger,NY(1959)
bombs, rockets, grenades, etc may include frag- 10)Glossary of 0rd(1959),30 ll)K. F. Ganz, ‘Nu-
mentation characteristics, penetration in armor clear Flight’, DuelI,Sloan & Pearce,NY(1960)
(or concrete), etc 12)F.I.Ordway & R. C. Wake ford, ‘International
Following are some refs on ballistic meas- Missile and Spacecraft Guide’, McGraw-HilltNy
urements and tests: (1960) 13) A. BaH,’Ballistic and Guided Missiles’,
l)C.J .Cranz, ‘Lehrbuch der Ballistic’, Springer, F. MulIer,London( 1960) 14)U.S.Military Standard
Berlin,vol 3(1927) and Ergiinzungsband(1936) MI L-STD-444, ‘Nomenclature and Definition in
2) T. Hayes, ‘Elements of Ordnance’ ,Wiley,NY the Ammunition Area( 1961 ),pp8-9 15)E.Burgess,
(1938) 3)M.Meyer, ‘The Science of Explosives’, ‘Long-Range Ballistic Missiles’, Chapman &
Crowell,NY(1943) 4)Anon, ‘Ordnance Proof Man- HaH,London(1961)
ual’ ORD-M608-PM(1 946) (Ballistic tests used
by the US Ordnance Installations are described BalIistic Modifiers for Cast Rocket Propellants
in detail) 5)1. Cohen, ‘Ballistic Testing of are discussed in the National Lead Co Repts
Rockets’, Lecture delivered at PicArsn,14 March for Project TU-2,Contract DA 30-069-501 -ORD-
1947 6)W.D.Chesterman, ‘Photographic Study of 2005( Conf)
Rapid Events’, Clarerldon Press,Oxford( 195 1) 7)
H.Stadler et al, Explosivst ]954, 144-8 & 1955, BalIistic Mortar Test. A brief description is
1-6 (Measurements in internal ballistics) 8)P. given under Physical Tests,pVII in Vol 1 of
Naslin & J .Vivi6, ‘Photographie et Cin6mato this Encyclopedia. See also J .Taylor & J .H.
graphic Ultra-Rapides’,Dunod, Paris(1956) 9) Cook, J .SciInstruments 26,266-8(1 949) (Improved
J. F. Roth, Explosivst 1957,161-76(25 refs) operation of the ballistic mortar for detg the
(Ballistic measuring methods) ‘power’ of HE’s)

Ballistic Missile. Any missile that is guided Ballistic Pendulum Test is briefly described ~
during powered flight in the upward part of its under Physical Tests, pp VII-VIII in Vol l(See
trajectory arid becomes a free-falling body in the also A. Schmidt, Explosivst1962,23-34)
latter stages of its flight toward its target. It
contains guided mechanisms, but is distinguish- Ballistic Pendulum Chronographs (B aUistis-
ed from a guided missile in that it becot-ms a chependel-Chronographe in Ger) are devices
free falling body, subject to the laws of bal- in which projectiles of a certain weight strike
listics, as it descends through the atmosphere. the lower part of a pendulum causing it to swing.
The missile is designed to travel in the outer The greater the swing, the greater is the veloc-
atmosphere or beyond it before plunging towards ity of the projectile. The theory in the design
its target. The German WWII missile V-2 and of these devices is based on the idea of Cassini
US Polaris, Pershing and Thor are examples of (1707), but it was Robins(1740), and Hutton
ballistic missiles (Refs 3,10 & 14) (1775) who consmucted the first appara~s.
Refs: l)U.D.Rose, ‘Die unheimlichen Waffen, Considerable work on the improvement of the
Atomraketen iiber Uns’,Schild Verlag,Miinchen aPParatus was done in France. The resulting
-Lochhausen(1957) 2)A.F.E :son Scholander, device of Didion-Morin-Piombert was used suc-
CRobotvapen’, Folkvorsvaret FOrlags AB cessfully, beginning in 1836, for many ye~s.
(Sweden)(l 958) 3)Interim GIOSSW Aero-Space Another apparatus of this kind was that of
Terms, Air Vniversity,Maxwell Air Force Base, Cheval-Minarelli-Fitzgerald, invented in 1901
Alabama(l~58),5 4)K.F.Ganz,Edit, CThe United Ballistic pendulum chronographs are not the
States Air Force Report on the Ballistic Mis- same as Pendulum Chronographs(qv )
 B

Re/:Cranz 3(1927),39-51 Nekrassoff, Contract NOrd 1026o(1954), Wash-

ington, DC, p 22 13)Anon,1Exterior Ballistics’,
BALLISTIE (Balistique, in FqBallistik, in Ger) USMilAcad,West Point,NY(1949) (P amphlet)
Ballistics is the science that treats of the 14)R.N.Wimpress,’Interior Ballistics of SoIid
motion of projectiles and is a particular branch Fuel Rockets’,McGraw-Hill,NY( 1950) 15)J.
of Applied Mechanics Comer, ‘Theory of Internal Ballistics of Guns’,
Ballistics has two major divisions: Wiley, NY(1950) 16)H.P .Hitchcock, ‘Handbook
A. Interior or Internal Ballistics- the study of of Ballistic and Engineering Data for Ammu-
Motion of the projectile while still in the bore nition’, Ballistic Research Lab, Aberdeen,Md,
of the gun. This includes the consideration of vols 1 to 4(1950) 17)F.R.Hunt,’Internal Bal-
the mode of combustion of the propellant, the listics’ ,Philosophicrd Library,NY(195 1) 18)Anon
pressure developed in the chamber, the velocity ‘Interior Ballistics’,USMilAcad,West Point,NY
of the projectile along the bore, etc (1951 ) (Pamphlet) 19)Anon, ‘Terminal Ballistics’,
B. Exterior or External Ballistics- the study of USMilAcad,West Point,NY( 1951) (Pamphlet)
the motion of the projectile after it leaves the 20)SACMS(Scienti fic Advisory Council, Min-
muzzle of the weapon istry of Supply) ‘Internal Ballistics’, Philos-
The branch of ballistics called Terminal Bal- ophical Library,NY(1951) 2 l)Anon,’Fundamentals
listics is concerned with the forces operating of Ballistic s’,Special Text ST 9.153, The Ord-
at the end of the projectile trajectory, that is, nance School, Aberdeen PG,Md( 1952) 22)
at the target. This is really a part of external Encyclopedia Britannica 2(1952),999-1006
ballistics, although this branch is sometimes 23)E .J .McShane, J .L.KeHy & F. V. Reno,’Exterior
referred to as a division (Ref 37) Ballistics’, Univ of Denver Press(Mimeograph-
Following is a selected list of books and pa- ed)(1953)(843pp) 24)M.Garnier,’La Balistique
pers on ballistics: Ext6rieure Moderne en France ‘, Irnprimerie
1)A. Brynk, ‘Interior Ballistics’, translated from Nationale,Paris( 1954) preprinted from MAF 28,
Rus by J .B.Bernadou, USGovt Printing Of f, Wash- 117-234(1954) 25)Anon,’Elements of Armament
ington,DC( 1904) 1 a)G.Schweikert, ‘Innere-Bal- Engineering’, USMiIAcad,West Point,NY(1954),
listik’,Leipzig( 1923) 2)C.J.Cranz,’Lehrbuch der Part ll,pp 85-110(Interior Ballistic s); ill-135
Ballistik’,Springer, Berlin,vols 1-3( 1925-1 927) (Exterior Ballistics) ;136-44(Bomb Ballistics);
and Erganzungen(1936), English translation by 145-64(Instrumentarion) and 165-6 (Terminal
the division of Armor and Ordnance, NDRC(1944- Ballistics) 26)W. Bevel ander,’Uitwendige Bal-
1945) (Mimeographed) 3)Gen P .Charbonnier, listiek’,Uitgeverij Excelsior, s’Gravenhage
‘History of Ballistics’,MAF 7,1227(1927) (Hollsnd)(1954)( Exterior Ballistics) 27)P.
4) G. Bruno, ‘Corso Teorico-pratico di Bal- Tavernier,MAF 29,73-158 & 513-618(1955);
istica Esterna’, Arti Grafiche Castello, Torino 31,303-390(1957); 32,37-109 & 591-695(1958)
(1934) 5)J .N. B ipgen, ‘La Technique de (Interior Ballistics, Theoretical) 28)H.L.Dry len
l’Artillerie’. L‘ Ecol e Royale Militaire de ‘Ballistics Research’,Ordn 40,893-7(1956)
Belgique,Br-uxedes, Vol 1, ‘Balistique Int6r- 29)P.Curti,Explosivst 1956 ,26976(A mechanic-
ieure’( 193>) .ald “Vol II, CBalistique Ext6rieure’ al solution of interior ballistics) 30)G.Seitz,
(1936) 6)T.Hayes, ‘Elements of Ordnance’, Explosivst 1956,248-56, 1957,7-11,53-7 & 187-
W~ley,NY(1938),65,96 & 397-468 7)H.Schardin, 94)(Computations pertaining to internal bal-
‘Deitragk zur Ballistik und technischen Physik’, listics) 3 l)Collier’s Encyclopedia 3(1957),
Barth, Leipzig(1938) 8)R. Winter,MAF 18,775-862 33-6 32) R. Schmidt, ‘Praktische Ballistik f~ r
(,1939); 19,3-75 & 199-270(1940); ~, 163-214 den Artilleristen,Erste Einhdmmg in die Aussen-
~1946) (Interior Ballistics) 9)H.Athen, ‘Bal- ballistik’, E. S. Mittler,Frankfurt a/M( 1957)
Iistik: Quelle & Meyer,Leipzig(1941 ) IC)T. 33)L.Besse,MAF 31,391-446,593-625 & 939-
Vahlen, ‘Ballistik’,W.de Gruyeter,Berlin( l?42), 1016(1957); 32,505-36 & 697-743(1958); 33,143-
reprinted by Edwards Bros, Ann Arbor, Michigan 239, 269-336, 555-608 & 807-926( 1959); 34,13-
(1945) ll)J.M. J.Kooy & J. W.H.Uytenbogaart, l10(1960)(Course of Exterior Ballistics)
‘Ballistics of the Future with Special Reference 34)L.Davis,J.W. Follin,Jr & L. Blitzer, ‘Ex.
to the Dynamical and Physical Theory of the terior Ballistics of Rockets’, Van Nostrand,
Rocket Weapons’, Technical Pub Co, Haarlem Princeton,NJ( 1958) 34a)H.Athen, ‘Ballistic’,
(1947) 12)M.E .Serebryakov, ‘Interior Ballistics’, Quelle & Meyer,Heidelberg( 1958) 35)W.C.
Oboronizdat,Moscow( 1949), translated by Dr. V. Nelson, Edit,’Selected Topics on Ballistics’,
 B8

NATO-AGARD,Pergamon Press,NY(1959) modification of early Ballistite in which NG

3~)R. E .Kutterer, ‘Ballistik’,Vieweg, Braun- together with a volatile solvent was used. The
schweig( 1959) 37)Glossary of Ord( 1959),p30 US at first adopted a double-base proplnt,
(under ballistics) hdurite invented by Munroe, but later switched
to Bernadou’s single-base proplnt Pyrocellrdose
BALLISTITE (Balistita in Span, Balistite in which was really a modification of Pyrocol-
Fr,Ital & Port, Ballistit in Germ & in RUS, lodion
B arisutaito in Jap). A successful double-base The so-called solventless propellants used
propellant invented by A. Nobel of Swederi in in great quantities at the present time are real-
1887-1888. One of the earliest compositions ly modifications of the Ballistite of Nobel
(patented in 1888) contained NG 50-60 & dry, The Ballistite contg 50-60% of NG caused
pulped, sol NC 50-40%. The fibrous structure of considerable erosion of gun barrels because
NC in this proplnt was destroyed, not by the of its extremely high burning temp due to the
use of a VOI solvent(as in the case of the con- presence of a large amt of NG. For this reason,
temporary poudre B), but by dispersing the NC later formulations of Ballistite were made with
in the powerful Iiq expl, NG, which functioned smaller amts of NG, partly replacing it with the
as a non-volatile gelatinize for the NC. In ‘cooler’ DNT. As this change involved decrease
order to facilitate the dispersion of NC in NG, in oxygen content, part of the sol NC(ca 12%N)
some benzene was added to the NG. After mix- was replaced with insol NC(ca 13%N), which
ing in a kneading machine, the benz was al- contains more O. The resulting proplnt was
lowed to evaporate and the remaining material called Super-attenuated Bullistite. Its compn
was passed several times through warm rolls was NG 25, DNT 15, 12%N NC 30 & 13%N NC
until it became homogeneous. Then the sheets 30%. It was used in WW1 by the French &
were rolled until the desired thickness was ob- Italians and proved to be nearly flashless
tained and cut into required shape and size. The Ballistites have been used as proplnts not
use of NS(nitrostarch) for part of the NC and only in cannon, but in howitzers, mortars and
the addition of pulverized chlorate or picrate in rockets as well
were also mentiongd in the paient of 1888 Following are some examples:
In Nobel’s patent of 1889, the use of cam- Brazil(Balistite). Admiral of Brazilian Navy
phor and volatile solvents (such as benz) was Alvaro-Alberto detnd some props(including
eliminated and the gelatinization was effected erosiveness) of several proplnts used in Brazil
by mixing NC with NG under w, heating to 80°’ among which was the Ballistite contg 50% NG
then rglling and cutting as above. In a mod ifica- & 50% NC(Ref 10)
.
tion of this process the gelatinization was France(Balistite), designated BALn, consisted
hastened by using an excess of NG and sub- of CPZ(NC contg ca 12%N) with at least 40% of
sequently removing it by means of 75% methanol NG; it was used in the form of square plates of
In the same yeat, Lundholm and Sayers, also various thicknesses; the thinnest of them was
of Sweden, proposed facilitating gelatinization used for launching bombs and grenades (Ref 4).
by bubbling compressed air through a slurry of Two formulations of Fr Attenuated BaHistite
NC, NG and stabilizers(such as aniline & chalk) are described in vol 1 of this Encyclopedia,p
in hot w. Under these conditions a dough was A506-L, under ATT
formed which was passed several times betw Gerrnany(BaIlistit). An older compn, WPC/89
rolls heated to 50-60°. Then ch~ sheet(carpet) (Wiirfelpulver/89), is described in PATR 2510
was cut into square flakes and these were glaz- (1958), p Ger 11. Brunswig(Ref 2) lists the
ed with graphite and blended. DPhA was used compn: NG 40, collod cotton 49, MNN 5, vase-
as a stabilizer in later formulations of bal- Iin 5.5 & moisture 0.5%. According to Pepin
listite Lehalleur(Ref 6), this proplnt was used in Nor-
As Ballistite proved to be very successful as way for rifles.
a proplnt, it was adapted by several countries, ltaly(Balistite). Several varieties have been
among them Germany and Italy, while some other used: a)Balistite norrnale o ordirzario(Normal
countries preferred single-base proplnts(poudre or Ordinary Ballistite), also called balistz’te al
B of VieiIle in France a&d Pyrocollodion of 50%, such as manufd during WWII by the Societ~
Mende16ev in Russia). At the same time GtBrit Dinamite Nobel, Avigliana, contained: NG 49.6
adopted Cordite, which is, strictly speaking, a *2, NC(N=ll.9t0.3%) 49.8*2, DPhA 0.54.3,

—
1
 B9

graphite 0.2+0. 15 & moisture ca O. 5%. Its props 0.75 & graphite(coating) 0.25%. Armament Engrg
are given in Refs 13,18& 19. Although this (Ref 22) gives for Ballistite used for rockets: NG
proplnt was very erosive, it was used on ac- 43, NC 51.5 & additives 5.5%. This seems to be
count of its high ballistic strength; b)Balistite similar to Ballistite JP 204 developed by Aero-
a basso titolo(Ballistite of low Strength), also jet Engineering Corp, Azusa, Calif which con-
called balistite al 42%, such as manufd by the tains: NG 43.0, NC(13.2%N) 51.6, K nitrate 1.4,
Societ~ Dinamite Nobel, Avigliana, contained: diethylphthalate 3.25 & DPhA 0.75%. To this
NG 42.5*1.5, NC(N=12.0*0.25%) 56.5t2, Et was added O. 16$’%of methyl cellulose(Ref 15).
centr 1.O*O.5, graphite 0.2 & moist 0.5%. Its Rinkenbach(Ref 11a) reported that thermal sta-
props are given in Ref 13; c)E?ulistite atterzuatu bility of Ballistite contg NC 69.25, NG 30.5 &
(Attenuated Ballistite), also called polvere DPhA 0.25% with graphite coating, tested at Pic
CGl 3, contained NG 25-26, NC(blend of collod Arsn, was satisfactory
cotton & gurrcotton) 60 & DNT 16-15% with a In Ref 23 is given the compn of B allistite JP,
stabilizer added (Ref 19); d)f?aZistite attenuata which is practically the s sme as for JP 204 ex-
aU’acetilcellulosa(Attenuated BalIistite Con- cept that JP apparently does-not contain methyl-
taining AcetyIcellulose), developed by Giua(Ref cellulose but does contain 0.1% nigrosine dye
l~,p 157) at the Societ~ Dinamite Nobel, con- Compositions of the following ballistites used
tained: NG 25, NC 60, acetylcellulose 10 & Et in rockets are given in Ref 15a:
centr 5%; e)Balistite al 60% contained NG 60 & JPH: NG 43.0, NC 54.5, EtCentr 1.0 & K sulfate
NC 40% with a stabilizer(added) l-2%(Ref 3). 1.5%, with added methylcellulose 0.16 & carbon
It was too erosive for use as a propellant in 0.10%
guns, but it proved to be very suitable as a JPN:NG 42.9, NC 51.4, EtCentr 1.0, K sulfate
bursting charge in some smaller caliber pro- 1.25, diethylphthalate 3.23, candelill a wax 0.02
jectiles such as 37/40mm HE and 37/40mm & carbon 0.2%
HEAP(Refs 14 & 21,P73) e) FiZite - the name Z?e~.s: l)Marshall 1(1917),301 2)Brunswig,Prop
for Ballistite in the form of cords(Ref 1) (1926),136 3)R.Molina, CEsplodenti’, Hoepli,
Japqn(Barisutaito). No info about its uses Milano(1930),393-5 4)Pascal(1930),227 5)Stett-
Ru;sia(Ballistit). No info on the use of Bal- bacher(1933), 194 6)Pepin Leballeur(1935),290
Iistite at our disposal. Burning characteristics 7)E.E.Sancho,’Qu~mica de Ios Explosives’,
of Ballistites were determined recently in Rus- A. Aguado, Madrid(1941),337 8)B.H.Sage & W.N.
sia by Pokhil et aI(Ref 24) Lacey, ‘Eztrusion of Ballistite Tubing and Rod’,
Spain(Balistita). According to Sancho(Ref 7), OSRD Rept 445(P BL 27280 ) (1942) 9)W. W.L acey
the Spanish and Italians used bcdistita IE, & B. H. Sage,’Some Physical Properties of Bal-
which contained more than 50% of NC. Its props Iistite’, OSRD 947(PBL 27283)(1942) 10)AIvaro-
are given,(but no. compn) by Vivas, Feigenspan & Alberto, AnaisAcadBrasilCiefic 14, No 4,341(1942)
Ladreda(Ref 17,P 89) who state that balistita is 1 l)Davis(1943),293-6 1 la)Wm.H.Rinkenbach,
manufd in Spain by the Sociedad An6nima de PATR 1359(1943),P2 and table l(Surveillance
Dinami:a de Gald5cano(Bilbao). When balistita and Heat Tests) 12)P6rez Ara(1945),413-14 &
is made in the form of tubes it is called tubelita 442-3 13)J.D.Parsons,PB Rept12663(1945), 15-16
Sweden(Ballistit). Early Ballistites of Nobel and 14)Anon,USNavy, BurOrdn Manual OP 1668(1946),
of Lundholm & Sayers are described at the be- 65 15)Aerojet Engineering Cotp Rept 194(1946),
ginning of this section, but no info is at our dis- 15a)W.W.Farnum, USNaval Powder Factory Tech
posal regarding current Ballistite. Stettbacher(Ref Rept No 15,1ndian Head,Md( 1947) 16)Stettbacher
5) describes the method of manufg Ballistite us- (1948),42 17)Vivas,Feigenspan & Ladred@1948)
ing machinery of the famous firm of Aktiebolget 89 & 99 18)Giua,Dizionario, 2(1949), 157 & 178
Bofors Nobelkrut(See Bofors Industries) (under Esplosivi) 19)Belgrano(1952),l 10-111 & 114
Switzerland(BaIlistit). Stettbacher(Refs 16 & 20} 20)Stettbacher, P61voras(1952), 52 21) Anon, ‘Italian
briefly describes the manur of Ballistites contg and French Explosive Ordnance’, TM 9~198~ ‘
40-50% NG and 60-50% collodion cotton. He also (1953),65 22)ArmmentEngrg( 1954),42 23)J.W.
states that BaHistites are used as rocket pro- Herrick, Edit, ‘Rocket Encyclopedia Illustrated’
pellants(Raketen-Treibmittel) USA(Ballistite). Aero Publishers, Los Angeles,Calif( 1959),40
According to TM 9~1904( 1944), p 96, the Bal- 24)P.F.Pokhil et al,DoklAkadN 135,913-16
Iistite used as propellant in trench mortars and (1960) & CA 55,26445(1961) Engl transln by
shotgun shells contained NG 39, NC 60, DPhA Consultants Bureau,NY 11 in Chemic4 Tech-
 1

B 10

noIogy Section, pp 193-5(5 refs) 1883) and by C. Renard & A. Krebs(France,1884),

electrically driven
Ballistograph is adevice used fordetg the All the above-mentioned airships(also called
velocity of projectiles in flight by a photographic dirigibles-hnd a very successful model con-
method. It has been employed in conjunction structed in 1898 by A. Santos-Dumont, a Brazilian
with a micro-time-measuring device caIled in Ger inventor living in Paris, were nonrigid. The first
‘Mikrozeitmess Instrument’. Both devices are rigid-type airship was built in Germany in 1897
described in Refs 1 & 2 by D. Schwarz. Its frame was of aluminum and it
Re/s: l)F.Duds, SS 19, 100-4(1924) & CA 20, was filIed with hydrogen. More successful was
732(1925) 2)Cranz, 3(1927), 329-335 the rigid dirigible Zeppelin invented ca 1900
During the 1st decade of the 20th century, air-
Balloons and Airships and Their Application in ship construction was carried on in most of the
War. A balloon is a bag of light non-porous ma- major countries and during WW1, airships were
terial(such, as paper, silk, rubberized cotton) used by the Germans(who built rigid Zeppelins),
filled with either heated air or a gas Iighter by Brit & French(who built nonrigid dirigibles)
than air(such as hydrogen or helium), The first and by Italians(who built semirigid airships)
balloon was constructed in France by the brothers Afier WW1 the Germans were prohibited from
Joseph & Jacques MongoIfier(1782) building airships(or airplanes), while Brit, Fr
The first balloons were so-called free balloons & Amer undertook extensive airship construction.
or aerostats. They could carry one or several The Amer firm of Goodyear Aircraft, Akron, Ohio,
persons, who rode in a basket attached by means built many heIium-fiHed nonrigid dirigibles, some
of ropes underneath the balloons. When balloons of them for the US Navy, others for commercial
are attached by cabIes to the earth or other purposes, such as advertising. About 1930 Brit
mooring they are called captive balloons. These and then in 1937 Fr abandoned the building of
are often used as observation balloons. When a airships. Meanwhile the Zeppelin Co resumed
free balloon is sent aloft without passengers its operation( 1937). As a result of this, at the
but with registering meteorological instruments, outbreak of WWII Germans had several modern
it is called a sounding balloon. A balloon used Zeppelins ready for service, while the Allies had
for investigation of high altitudes(such as 70,000 only a few nonrigid balloons, commonly known
ft or higher) is known as a stratosphere balloon. as l?limps. In the course of WWII many more
The so-called pilot balloon is a small free bal- blimps were constructed for the US Navy and
loon sent aloft to show direction of the wind. they were used successfully against Ger sub-
The propaganda balloon is a small sphere de- marines. At the same time, the hangars and pro-
signed for spreading propaganda literature over duction facilities of the Zeppelin Co were de-
enemy territory. This work is now accomplished stroyed by bombing and this ended Germany’s
almost exclusively by airplanes. A kite bal- airship activity
loon, such as that of Drachen or of Capt Caquot, The post WWI.I period of aeronautical develop-
is an elongated form of captive balloon (common- ment began with only US and Russia engaged in
Iy known as sausage) which is flown at a con- airship construction and this only to a limited
siderable inclination to the horizon in order to extent due to competition from airplanes
attain ‘kiting’ effect. The Caquot balloon was Balloons, Application, in War. The first use of
used by the British during WW1 for observation balloons by the military appears to date from
purposes, especially for spotting submarines the period of the French revolutionary WSrS(1789-
(see below under Balloons, Applications in War) 99), when a ‘corp of aeronauts’ was formed and
Until about 1850 none of the balloons could be sent by the French in balloons over the Dutch
propelled or steered. The first balloon which add Austrian troops. The unexpected appearance
could be successfully propelled and steered of balloons had a demoralizing effect on the
(airship) was constructed in 1851-2 in France enemy and caused them to retreat. Later( 1812),
by H. Giffatd. It was equipped with a steam en- the Prussians employed balloons against the
gine which rotated a propeller. The ship could Napoleonic troops, but without great success.
move at a speed of 6mph. Higher speed was Balloons were also used for bombing purposes,
attained by later models, such as the one of as briefly described under Bombs, Historical(see
P. Haenlein(Germany, 1872) driven by an internal under BOMBS)
combustion engine; by A. & G. Tissandier(France, In the Amer Civil War( 1961-5) balloons were
 B 11

used for observing and photographing the en- 4)Collier’s Encycl(1957), 12,378-83 (under ‘Light-
em y’s terrain and troops. Again, balloons were er~an-Air Cra~t’) 5)M erriam-Webster’ s(1961 ~
used during the France-Prussian War(1870-1) 167-8
(such as for evacuating some Govt officials from
besieged Paris), in the campaign against Tonking Balloon Barrage. As origiiially developed in Gt
(1880’s), in the Bechuanaland expedition(1880’ s), Britain during W’Wl, a baHoon barrage involved
in the Spanish-American War(1898) and in the the reIease at a m ax height of 1000Oft batteries
Russo-Japanese War(1904-5). With the advent of of three kite balloons (sausages) of IUOOOCU ft
WW1, every major power began to pay more atten- capacity each, one at the center and ofie at each
tion to war balloons. The captive balloons end of a horizontally floating cable 1000ft in
(sausages and blimps) were used in balloon length. From this was suspended, at regular in-
barrages and forobservation purposes. One tervals, a series of steel wires trailing earth-
of the methods used to spot a submarine was to ward like flexible teeth in an enormous comb.
attach, by means of a cable, a balloon manned An attacking airplane was thus forced either to
by one or more observers in a basket below, to rise above this contrivance or to dive below it.
a destroyer or other ship going to sea for patrol- In the first case, the height would be too great
ling purposes. The use of power-driven balloons to permit accurate born bing(at this time), while
(airships or dirigibles) was not only for observa- in the second case a plane would risk exposure
tion purposes but also, to a limited extent, for to the effects of point-blank AA fire
bombing(especially by Ger Zeppelins) With the advent of WWII, the barrage ceiling
An ingenious application of balloons was made was increased to 15000ft and balloon barrages
by the Japanese during WWII. They constructed assumed new importance, especially in the de-
ca 1000 paper balloons, spherical in shape and fense of London
33 ft in dim. The balloons were filled with hydro- Similar ‘sausages’ tow’ed singly by destroyers
gen and could stay in the air for ca 1 week at a or merchant vessels, served as barrages in the
an altitude of ca 5 miles. A basket suspended defense of convoys passing through the English
underneath each balloon contained a bom~in- Channel because they rendered hazardous any
cendiary or antipersonnel), two self-destroying attempt by hostile air raiders to carry out dive-
devices, batteries activated by solar energy, bombing operations
several paper bags with sand(used as balIast) Refs: l)Anon, ‘Barrage Balloon Manufacturing’,
and devices for maintaining the balloon at the Manufacturers’ Record 112,36-7(1943 ) 2)E ncycl
desired altitude and for bringing it down some- Britannica 2,(1952), 1011 3)Collier’s Encycl(1957)
where on the North Amer continent 12,380(under ‘Lighter-than-Air Craft’)
The balloons were released from Japan one by
one in the autumn of 1944 to be carried by easterly BALL POWDER or BALL GRAIN POWDER
winds(prevailing at an altitude of ca 5 miles) (Glob~ar Propellants or Olin Ball Powder)
toward Canada or the US. These balloons de- (Poudre sph6rique in Fr; P61vora W in Span,
cended mostly in the Pacific coast area, such as where W stands for Western; P erlpulver in Ger).
Brit Columbia, Washington, Oregon & a few in The process for the manuf of this proplnt was
Calif. Some balloons were carried to central or developed ca 1935 by Fred Olsen,Director of
even eastern parts of Canada and the US. Total Research, Western Cartridge Co, Division of Olin
number of recovered balloons was ca 300, but many Industries, Inc(now called Olin Mathieson Chemical
unquestionably have remained undiscovered be- Corp),East Alton,I1l. The process bears little re-
cause of the vastness of uninhabited territory on semblance to conventional methods of msnufg
this continent. Some of the ballmns travelled proplnts and results in a product that is unique
6000 miles in 4 days at an average speed of ca in the ezpls industry. The proplnt consists of
70 mph small spheres, not larger than 0.030” in diam.
The damage caused by bombs(incendiary or HE) Ellipsoids can be obtained by flattening the
carried by Japanese balloons was. negligible(Ref spheres by mechanical devices
1) Manuf of ball proplnt consists essentially of
Re/s: l)R.W.McKay, ‘J apanese Paper Balloons’, the following operations, as described in Refs
Engineering Journal 28,563-7( 1945) 2)Merriam- 1-4:
Webster’s(1951) ,209 3)EncyclBritannica( 1952) A. Shaping O{ Propellant, also called Granulating
1,464-71 (Airships) & 2,1006-10(Balloons) or Hardenin~
 B 12

a)NC of 12.4 to 13 .4%N, previously pulped, sub- Note: The operations described above are applic-
j ected to a short preliminary boil and washed with able to any single-base proplnt. In order to pre-
cold water(to remove the bulk of acid), is placed p-e a double-base proplnt, the required amt of
on a ‘nutsch’ or a centrifuge to remove the bulk NG(or NG + NGc) in a suitable solvent is added
of the water. The slight!y wet NC is loaded into at this stage of the process and dispersed un-
drums and transferred from the NC plant to the iformly throughout the quasi-emuIsion. Substances
‘ball powder plant’ like DNT, TNT, DBuPh, centralizes, etc may be
Note: Instead of using straight NC, a mixt of NC incorporated, if desired in the same manner as
and some reworked or deteriorated smokeless NG
proplnt may be used. The grains of proplnt larg- e)The next operation, which consists of breaking
er than 80-mesh must be previously reduced in down the lacquer into small spherical particles,
size by treatment under water(buffered to ca pH is of utmost importance and requires skillful
7.2) in a hammer mill. Treatment in w will re- operators and ca one hour of time
move the acidic decompn products of NC but will f)With the agitator blades adjusted to shear off
not remove the nitroso- or nitro- derivs of DPhA, portions of the lacquer, and with the colloidal
if they are present. In this case, the addn of a soln being agitated rather rapidly, a small quan-
Iwger runt of DPhA than usual would be required tity(l-2% of the total amt of ingredients) of an
in subsequent operations aq dispersion of a glue-like substance, such as
b)The NC is unloaded from drums into a sump starch, dextr~n, gum-arabic, bentonite, animal
and then, after mixing with an additional amt of glue, etc(called the ‘protective colloid’), is
w the NC is pumped as a slurry into a closed, added to the contents of the ‘shaping tank’. As
stainless steel, cylindrical jacketed vessel, a result of this operation the NC lacquer is
known as shaping tank(capacity 3201 to 84001bs broken down into small spherical particles which
of finished product). The vessel is provided with are suspended in the water phase. If the pro-
a vertical condenser for recovery of solvent tective colloid is not added, the grains of proplnt
vapors and a mechanical agitator which is driven which form during stirring coalesce, forming a
through a Reeves variable speed drive by a motor continuous gelatinous mass as soon as part of
situated in an adjoining room the soIvent is removed
c)The shaping tank is filled to a predetnd level Note: The probable theoretical explanation of the
with w contg some finely pulverized or pptd formation of globules from the lacquer in the
chalk, after which steam is introduced into the presence of a protective colloid is given by
jacket and a volatile org liquid, such as ethyl Olsen in Ref 1, pp +4 under ‘Operation’
acetate( which is a good solvent for NC but is g)The size of the globules, and of the grains
immiscible with w), is added while the agitator is formed later, depends upon a number of factors:
in motion. A small amt(ca l% based on the final the grain size decreases with increase of rotor
product) of stabilizer, such as DPhA, is usually speed, with increase in percentage of protective
added to the et acet before it is poured into colloid present and with decrease(within certain
the shaping tank limits) of the inherent viscosity of the NC
Note: The amt of et acet used should be such as (viscosity of a given wt of NC in a given quantity
to make a lacquer contg 15 to 25% of NC. The of std solvent). Other factors, such as tern p,
viscosity of this lacquer should be from 300 to agitation tim e, the shape of the agitator, the
2500 sees at 25° by the Falling Ball Method. As type and quantity of colloid added, and the rate
the lacquer is lighter than w, it has the tendency of removal of the solvent, also influence the
to rise to the surface size of the grains
d)After raising the temp to ca 50° and agitating Note: Proplnts fofi various purposes range in
for ca 30mins, all the NC goes into soln and the finished sphere diam from 0.006” to 0.030”, but
mineral acid(mostly sulfuric), which was tenacious for any pW-titular proplnt, a rather close toIerance
ly held by the NC fiber, is released. The agita- of sizes is desired. For instance, 0,006 to 0.010”
tion disperses the lacquer in the water phase for US cal .45 ammo; 0.010 to 0.014s for M-1 car-
(forming a quasi-emulsion) and washes the acid bine; 0.015 to 0.030” for US cal .30(1? 06) ammo
,.
out. The fine particles of chalk, which are pre- and 0.025 to 0.030” for US cal .50 and the 37mm
sent in the mixt, neutralize the acid, leaving cannon
the neutral and stable NC dissolved in et acet h)The next opern, consisting of dehydration of the
 B 13

grains, is also of great importance because if it gradually (within 6S reins) to 72°. After case-
is not done properly the shape and density of hardening, the temp is raised to 95° and maintain-
the resulting grains will not be as required ed until the VOI Iiq is completely expelled
The first step in this opern is to remove the k) The distilled vol Iiq, mixed with w, passes
small amt of w which is dispersed(or emulsified) from the condenser to a separator which is a
in the gIobuIe of NC lacquer. ShouId this w be cylindrical vessel provided with a gage and
left through subsequent operations, the final valves. Here, et acet collects at the top and thus
ball grains would be porous and of low density. separates from w whi ch forms the bottom layer
If, however, the w is removed before hardening l)At the end of the disth, the contents of the
of the grains, too high d material is obtained. tank are allowed to cool to ca 50° and then are
The removal of w is achieved by dissolving an pumped as a water-slurry to a cylindrical tank
inorg sslt(such as Na sulfate) in the water phase (provided with an agitator) placed above the
in order to set up an osmotic pressure gradient rot~ wet screens. The re suiting proplnt grains
betw the w dispersed in the grains and the w in contain ca 1% of residual VOI Ii q and the variation
the tank. As a result of this, the w migrates from in disrn of the spheres may be as high as 0.02”
the grain through the NC lacquer(which acts as Note: Due to the fact that a completely closed
a semi-permeable membrane) to the Na sulfate system is used in the shaping tank, the losses
soln in the tank of vol liq are very small(ca 3%)
Note: As a rule, high d of grains can be achieved & Wet .$creenirzg. In order to achieve closer size
by dissolving a larger smt of inorg salt.. The d separation than could be done in the opns de-
may also be controlled by the temp and the time scribed above, the hardened balls are washed
i)when the grains have assumed the desired shape free of shaping tank Iiq(which consists of an aq
the next step is to remove the volatile Iiq(such soln of Na sulfate and all the protective colloid)
as et acet) by distillation. For this operation a and are then rum through two or more rotary wet
condenser is connected by a pipe to the upper screens(such as the Trommel type) each of which
part of the shaping tank and the tem~ in the tank separates two fractions: ‘through’ and ‘on’. By
is raised to the bp of ~he vol liq (69° for et acet). using various series of screens, as many fractions
During the distillation period, the contents of the as desired can be separated, most of which are
tank are kept ,agitated but at a lower rate thm usable directly in one grade of proplnt or another
during the shaping period After sizing, the aq suspensions of grains are
Note:Rate of removal of the vol liq is a determin- stored in c ylindricsl, agitated storage tanks from
ing factor of grain size and care must be taken which they can be pumped to the coating still,
not to remove the liq too fast - otherwise hoI- capacity up to 120001bs
low and porous grains, having the appearance of C. Deterrent Coating. If the proplnt prepd as
popcorn, are obtained. If, however, the liq is evap above is used as such, it would be depressive
at too slow a rate and at a temp below its bp, burning. Inasmuch as the design of c~ent
extremely dense spheres are obtained. As a rule, weapons is based on the use of progressive
the rate at which the vol liq can diffuse through burning proplnts, the initial rate of burning of
the lacquer depends upon the viscosity and there- balls must be reduced to such an extent that
fore upon the am t of VOI Iiq present in the grain. the proplnt wilI become more or Iess progressive
The rate of diffusion must exceed the rate of burning. This may be achieved by coating the
removal of vol liq from the tank(by distn) or a balls with a slow burning material, called deter-
hard skin(case) is formed around each globule. rent, and the following method can be used:
As the skin would not soften, the resuiting grain a)To the agitated aq shmry of uncoated proplnt
would be hollow i n the coating still is added the desired amt(such
j)To achieve the best results in distn, the sol- as 5-10%) of deterrent agent(such as DNT, di-
vent must be removed at a fairly rapid rate at butyl- or diphemylphthalate, etc) in the form of
the beginning and at a decreased rate later until an aq emul sion. In the case of a material such
the grains become case-hardened. After this, the as DNT, an emulsifying agent, such as saponin
rate of distn can be reasonably increased until in w, can be used
the complete hardening of the grains b)With steam heat in the jacket, the charge is
As an exampIe, OIsen(Ref I,P4) sugge=s st~t- continually agitated until the deterrent has
ing the distn for high d proplnts at 68ysl below penetrated to the desired depth on the surface
the bp of et acet) -d then raising the temP of the balls. This might take from 4 to 15brs for
 I

B 14

a 12000-Ib batch belt dryers which are equipped with infrared lamps
Note: Coating with a deterrent not only modifies for heat supply
the rate of burning of the proplnt, but it also According to Olive(Ref 7), the damp proplnt is
renders the grains waterproof fed directly to the belt ( made of rubber or can-
c)The slurry of coated grains is pumped to the vass, 48” wide and 80f t long, from a hopper contg
feed tank from where it can be sent either to the an agitator. One hundred and forty 250watt infra-
rolls(if the grain web is to be reduced in size) red lamps are placed in 28 rows about 18” above
or directly to the top-feed filters(if the rolling the proplnt layer on the belt, being more closely
operation is considered unnecessary) spaced at the entrance end of the damp material
Note: If it is desired to have the grains easily than at the exit end. The ensemble is enclosed
ignitable, they are coated with an accelerator in a long chamber made of light metal panels, in-
(such as NG) instead of a deterrent. For this, a sulated and hinged, to serve as explosion hatches.
20-30% soln of NG in alc or in benz is added to A small amt of air, preheated by steam coiIa to
the contents of the coating tank and the slurry ca 50°, flows counter to the proplnt movement to
is agitated in the same manner as for coating carry away the moisture. The heat is regulated in
with a deterrent and the desired smt(5-lwO based such a manner that the temp of the material is ca
on the dried wt of finished proplnt) of NG is added 72°, as shown by thermocouples riding on the sur-
D. Wet Rolling. Since the ballistic performance face of the moving layer of proplnt. With the a-
of a proplnt depends to a great extent upon the bove installation, 1401bs of proplnt can be dried
thickness of the web of the grains, it is important in 1 hr with an av consumption of O. 196kw-hr per
to have it as uniform as possible. As it is diffi- lb of dry proplnt. Drying time takes ca 1 br
cult to prep all the balls of exactly the same In the absence of an infra-red dryer, the pro-
diam, the simplest way would be to select a batch pellant may be dried in conventional dryers(such
with S1 larger grain diam than required and then as a tray dryer) but it takes a longer tim e(6 to
to slightly flatten the balls to form ellipsoids hav- 10hrs)
ing their minor diam that corresponds to the de- Note: In any case, drying of ball powder is much
sired web thickness. This is done because the quicker than drying of conventional proplnts,
time of combustion of an ellipsoid(or a similar which usually takes several days
flat grain) is the same as that for a ball of diam G Glazing. In order to prevent the formation of
equal to the minor diam of an ellipsoid, provided an electrostatic charge, the’ proplnt is glazed
that all the grains have the same compn and d. with graphite. For this, the dried material is
Ellipsoidal-grain proplnts are called in France loaded into cans and transferred to the glazing
poudres sph~riques ecras~es and they were in- bldg, where it is weighed @ 1200-lb batches to-
ve stigated by Tavernier(Ref 14) from the theoret- gether with 2.5 to 61bs of powdered graphite.
ical point of view Then each batch is rotated in a conventional
Rolling may be accomplished by passing a sweetie banel until a uniform black glaze and
thick slurry of hot balls betw the faces of two the desired moist content are obtained(which
highly polished, cylindrical rolls set together in takes ca 2hrs)
such a manner as to reduce the web size so that H. Dry Screening. The glazed proplnt falls by
the variation in diam is ca t 0.001” gravity onto a conventional shaker screen, the
Note: If for some reason it is not desirable or putpose of which is not only to remove the over-
convenient to roll the ball powder, the equal time size and undersize balls, but also any impurities
of burning of sm all and large grains may be which may have been picked up during previous
approx achieved by surface-treating the larger operations
grains with an accelerator(such as NG) and the 1. Blending, Packing and Magazining. Since each
slower grains with a very slow deterrent, such batch might have SI different props, the best
as some phthalate
practice is to thoroughly mix several batches so
E. Filtering and Centrifuging. Before the proplnt
that the resulting blend will have intermediate
is sent to the dryers, it must be dewatered to
props. By so doing, it is possible to obtain large
8-15% H20 content(depending on the nature of
batches(called lots) which are practically identi-
the material) by passage either through a centri-
cal. The blending is done in a conventional
fuge or through a top-feed vacuum filter, such as
blender, which consists of a tall tower in which
the Oliver type
the proplnt, first elevated to the top floor, grad-
F. Drying is usually accomplished in continuous-
 B 15

ually descends bygraviry through a succession not need to be conventionally stabilized but
of hoppers and knife edges where the flow is re- simply sour-boiled and washed with cold w. Not
peatedly divided and recombined only is freshly prepd NC suitable for ball powder,
After blending, the proplnt is sampled, packed but also any discarded or reworked NC or smoke-
in a number of airtight cans and transferred to a less proplnt may be utilized
magazine for storage. After inspection and ac- b)The process of m anuf is safer than for conven-
ceptance tests, the proplnt is either used for tional proplnts because all the opns previous to
loading ammo or left in storage until needed drying are carried out under w and transfers of
Note: If a proplnt of uniform-sized balls does not the NC are done by pumping it in a state of
possess the ballistic props required for a given water slurry
weapon, materials of different grain size may be c)Much simpler and less expensive equipment is
blended to secure such props(Refs 1-7 & 21-22) used in the ball powder process than in manuf of
The method of manuf described above may not conventional proplnts. No hydraulic presses are
be exactly the same as currently used because required
many modifications of the original Olsen method d)Shorter number of man-hours are required for
were proposed in the last 15 years production of unit wt of ball powder. The process
Laboratory Method of Preparation of Ball Powder. is less expensive to operate than the conven-
Take a wer, puIped NC(N=ca 12.6%) of known tional process for proplnt m anuf
water content and weigh 60g(on a dry basis), e)Since the operation involving a volatile liquid
Transfer to a 2-1 fluted round-bottom, 3-neck flask, is conducted in a cIosed vessel, the losses of
provided with a stirrer, and add 200ml distd w. VOI liq are very small(ca 3%)
Add, while stirring, lg of 2-nitrodiphenyIamine The ball powder itself possesses the following
dissolved in 450ml ethyl acetate. Start to heat advantages: a)It can be made either as single- or
very slowly and add any other required ingredi- double-base proplnt using the same equipment
ents, such as DNT. If the proplnt is intended to b)It flows and Gcreens very easily c)It possesses
be double-base, the prescribed amt of NG or a higher thermal stability than any of the known
DEGDN, dissolved in a suitable scdvent, is added extruded proplnts d)It possesses uniform d of
at this stage. After raising the temp to ca 50° loading and it is possible to secure, even by
and agitating for about 30 reins, sII the NC goes volumetric loading, charges in which the ballistic
into soln forming a lacquer. After increasing the characteristics can be accurately controlled e)
agitation to a rather rapid rate, add ca 120mI of There exists the possibility of varying the d of
20% aq gum srabic soln or any other suitable grains when desired to secure slower or faster
protective colloid such as methyl cellulose. As burning proplnts f)Less gun barrel erosion than
the result of this operation, the NC 1acquer is for conventional proplnts g)The possibility of
broken down into small spherical particles which manuf of some types of rocket proplnts by mixing
remain suspended in the water phase. Since these ball powder directly in the rocket moror with a
particles contain some water, it must be removed non-volatile solvent and then allowing the thick
before the next operation. For this, add to the slurry to set to a solid or semi-plastic mass
slurry 50g Na sulfate dissolved in 200ml of distd Following are some disadvantages of ball
w preheated to ca 60°. When the grains have as- powder: a)Impossibility of producing balls larger
sumed the desired shape, start to remove the et than about 0.030” in diam. As such small grains
acet by distillation. For this, heat the slurry are comparative y fast b~ning they are suitable
gradually to 69°(bp of et acet) while continuing only for smaller ammo- up to ca 37mm b)Im pos-
the agitation and then finally heat to 72-75°. sibility of making alI grai ns of the s sme batch
There is no necessity to heat the sIutry to 95° exactly the same size c)Impos sibility of incorp-
as is done in plant operation orating water- soIuble salts, such as K nitrate or
Cool the slurry to ca 50° and either centrifuge Ba nitrate, in the balls because these salts
it or filter through a B!ichner. Wash the balls would be diffused in water during the m anuf. Even
with cold distd w to remove the protective colloid some of the insol salts(such as lead stearate)
and Na sulfate, spread the proplnt on a filter cannot be incorporated in the balls
paper and dry it Re/s: 1 )Fred Olsen, G. C. Tibbitts & E .B. W.Kerone,
Following are some advantages in the msnuf USP 2047114(1936) 2) F. Olsen & G. C. Tibbitts,
of ball powder over conventional proplnts: uSP 2111075(1938) 2a)H.F.Schaefer, USP 2160626
a)The NC required to manuf ball powder does (1939) 31F.Olsen,G.C.Tibbitts & E. B. W. Kerone,
 I

B 16

USP 2175212( 1939) 4)Ibid,USP 2206916(1940) Na nitrate, charcoal & sulfur

5)Davis(1943),328-306 )A.Stras~er,pATR 1459
( 1944) (A study of consolidated ball powder from BAm or B(AM) (Poudre) (Fr). See under B(Poudre)
Western Cartridge Co) 6a)C.E.Silk,USP 2375175 (’45)
& CA ~9,3672(1 945) (Spherical grains of smokeless BamboocelIulose Nitrates. B. Rassow & A. Reck-
proplnt) 7)T.R.01ive,ChemEngrg ~,No 12,92-6 & eler,NitroceHulose 3,41-45 & 61-64(1932) prepd
136-9(1 946) (Ball-powder process upsets expls a product contg ca 11.3%N by nitrating an Indian
industry tradition) 7a)Stettbacher( 1948)- not de- bamboo for 2hrs at 20° using 30 parts of mixed
scribed 8)Riegel, IndChem(1949),718-19 9)P. acid consisting of 19.8% nitric acid, 66.7% sul-
Tavernier,MP 31, 208-10(1949) (Density of ball furic acid & 16.5% water. A Japanese bamboo
powder) IO)E.P .Reichardt & B. C. BaIdridge,USP gave under the same conditions a product with
2543535(1951) & CA 45, 5930( 1951)( The bal- ca 10.8zN. The yield in both cases was compar-
listic prop of ball-type proplnt can be regulated able to that of cotton or woodpulp
by controlling the amt of w left in the grain prior
to rolling) 10a)Belgrano( 1952)- not described Banana Oil. See Amyl Acetate in VOI l,p A678-L
10b)Stettbacher, P61voras(l 952)- not described of this Encyclopedia
11 )Anon,Explosivst 1953,41 -42(prepn of ball
powder) 12)J.Fauveau & J. Chosson,MP 35,183-90 Bangalore Grenade (Granata bangalore in Ital).
(1953) (Surface treatment of ball powder in liquid According to Molina,Esplodenti( 1930),374-5,
medium) 12a)G.R.Cox,USP 271 5574(1953) & CA this is a hand grenade using dry guncotton(ful-
49,1 5542(1955) (Prepn of high-d ball powder) micotone, in Ital) as a bursting charge
13)Anon,Explosivst 1954,46 (B all powder is now
m anuf by the P oudreries R6unies de B elgique, BANGALORE TORPEDOES; Detonating Cables;
mainly for use in caliber .30 cartridges adopted Demolition Hoses and Demolition Snakes. These
for the official NATO rifle, which was developed are long demolition devices which are intended
in Belgium) 14)P.Tavernier,MP 38,193-232( 1956) chiefly for clearing mine fie Ids and for blasting
(Ball powders and rolled ball powders; theory) passages through wire entanglements. There are
15)J.J.O’Neil,Jr & G. R. COX,USP’S 2740704-5 also some other uses indicated below
(1956) & CA 50,9742( 1956) (MwNIf of ball powder) Bangalore torpedoes exist in several modifica-
16)J.J.O’Neil,Jr Ordn 41,365-7 (1956) (Manuf of tions. The std US device, Ml A2 which was used
ball powder by Olin Mathieson Chemical Corp) successfully during WWII, consists of 10 loading
17)W. A. Schmelling,Badger Ordnance Works, assemblies, 10 connecting sleeves and 1 nose
TechRept NO 176(1957) (Reclamation of NC and sleeve. The loading assembly consists of a steel
NG from scrap double-base proplnts for use in tube 5 ft long and 2 1/8” in diam, filled with 7.61bs
ball powder manuf) 18)J.H.Herd,Naval OrdnaQce of 80/20 amatol (or other solid HE) and topped off
Lab. NavOrd Rept NO 6131( 1958) (Approval of by 4“ of TNT(ca 1.4 Ibs) at each end. Each end
ball powder type WC-86O for use in the explosive is capped and grooved and cent ains a fuze well
actuator MK 4 MOD O) 19) J. J. O’Neil & G. R.COX, to accommodate a detonator, primacord, or a blast-
USP 2830886(1958) (A process for the manuf of ing cap(such as Corps of Engineers Cap, called
globular proplnt) 20)R.L.Cook & E. A. Andrew, now Cap, Blasting Special, described in Ref 14
USP 2888713(1959) & CA 53,16541(1959) (A con- or a commercial one not smaller than No 8) attach-
tinuous process for manuf of globular proplnt) ed to any of the std firing devices. Initiation may
21)C.M.Reinhardt, USP 2919181 (1959)(A process also be accomplished by a detonator or four turns
for manuf of globular NC) 22)P.F.Schaffer, formerly of primacord wrapped around one end of the tube.
of P icArsn; private communication 23 )E. F .Steven- The torpedo may be used as a single tube or
son & W. P. Morton, Jr, PicArsn; private communica- several tubes(called loading assemblies) may be
tions 1960) fastened together by means of connecting sleeves
as shown on Fig 222,P 37 in Ref 2 and Fig 192,
BALn. A Fr propellant. See under Ballistites p 266 in Ref 5. A nose sleeve with a rounded
point is provided for ease in pushing the torpedo
Balsa Wood Nitrated. W.de C. Crater,USP 2174914 through obstaclestRefs 2,3 & 5)
(1939) & CA 34,887(1940) proposed several expls A short length of bangalore torpedo can be
mixts contg nitrated baIsa wood of N content 9 to used as an antitank(A/T) or an antipersonnel
11.5%, as for instance: nitrated balsa wood, AN, (A/P) mine or as a booby trap. It was also used,
 B 17

according to BaH(Ref 4), by US troops for de- no gravel or stones. The shell was then placed
struction of piIl boxes during the attack on the at an angle of ca 30° in the desired direction and
Siegfried Line in March 16, 1945. For this, a the fuse lighters on both the shell and the cord
5-ft length of bangalore torpedo, equipped with a were pulled out. The shell acting as a rocket was
pull fuze, was dropped inside a narrow vent pipe propelled to a distance of ca 200ft while dragging
sticking out the top of each Ger pill box. This the detonating cord with it. After several seconds
was the idea of an unknown Amer soldier and the detonating cable exploded. For a m ore de-
the device was fired after the bazooka shot and tailed description of this device, see Ref 1, pars
the pole charge failed to penetrate completely 46.04-a to 46.@i-i Demolition Hoses, used by
through the vent some European countries, such as Germany and
A more recent US bangalore torpedo is the Czechoslovakia, were long flexible hoses made
M1A2. It is described in conf Ref 6, but in un- of various materials. One end of such hose was
classified Ref 12 it is mentioned that its chge is stationary while the other end could be projected
9.5 Ibs of Comp B or Comp A-3. The US Military to a desired distance across a mine field or other
specification requirements are in Ref 13 obstacle by means of a rocket, mortar projector
Detonating Cable can be used for the same pur- or other device. Then a liquid expl, such as
poses as a bangalore torpedo. A std US device Myrol, which was used by the Germans(Refs 8 &
Ml for clearing narrow lanes in A/P mine fields 10), was pumped into the hose and the explosive
consists of a nylon-covered cable(also called detonated by means of a conventional initiating
rope), 170ft long and ca 1“ in diam, which con- device placed at the stationary end of the hose.
tains 46 Ibs of oil-soaked PETN(regular detonat- The Czechs used a device called Hadice which
ing cord should not be used as a substitute). The is briefly described in conf Ref 7
cable consists of 19 strands of special detonat- Demolition Snakes, intended principally to breach
ing cord, each contg ca 100 grains PETN per ft. minefield, may also be used to breach bands of
One end of the cable(which contains a booster log posts, steel rails, antitank ditches snd some
chge and a threaded cap well for inserting a 15- small concrete obstacles. A demolition snake con-
second delay detonator for exploding the cable) sists of sections made up of two parallel linear
is anchored to a stake driven into the ground, chsrges of expls encased betw corrugated metal
while the other end is projected across the mine plates, bolted together to form an assembly rigid
field by a JATO unit. The cable is then exploded enough to be towed or pushed by s, light or med-
by the detonator at the anchored end(Ref 5,pp 287- ium tank yet flexible enough to pass over uneven
8). In the older device, which was used during ground. Detonation of snakes was accomplished
WWII, the cable(rope) consisted of 13 strands of from within a moving or stationary tank by the
detonating co+d 215ft long. In prepg the cable, impact of a .30 cal bullet from a machine gun a-
the 13 strands(cords) were held by several men gainst a vertical plate forming part of the two
and wrapped with twine and tape. One end of the impact fuzes, one attached toward the leading end
cable was attached to the ground and provided and one at the rear of the charged segments of
with US Army Special Nonelectric Blasting Cap the snake assemblv
(described in Ref 14), a 15” length of time fuse The demolition snake M2, described in Ref 1,
and a lighter. The other end of the cable intended pars 46.o2 to 46.03 and in Ref 5,pp 288-9, is the
to be projected across a mine field was attached earliest model. It was made of corrugated steel
by means of manila rope to the body of a 105mm plates. The usual length of this snake was 400 ft.
base-ejection smoke shell(M84), modified to The chge consisted of 10 Ibs of 80/20 amatol per
function as a rocket. For this, the empty shell ft. The first 20ft of the snake atid rear 60ft con-
with fuze deactivated was placed upside down tained no expl. This prevented premature explns
and, after removing the base-plate, about 1“ of while pushing, or towing. Gross wt of a 400-ft
earth dirt was temped in the nose of the shell to snake was ca 7 tons. Snake M2A1 was similar
seal off the hole leading to the fuze. This was to M2 except that its load was 14 Ibs of amatol
followed by ca 150g of propellant wrapped in a per ft. Gross wt of a 400-ft snake was ca 8.5 tons.
cloth and provided with US Army Special NotI- Snake M3 is the current model. It is described in
electric Cap, described in Ref 14, a 12” length unclassified Ref 5,P 289. The snake is 14” wide,
of fuse and a lighter attached at the base of the 5“ high and 400 ft 1 ong when assembled. Cor-
shell. The remaining space in the shell was rugated aluminum plates, 9ft long, fastened with
filled and lightly tamped with earth containing steel bolts, washers and Iuws, form the body of
 1

B 18

the snake. A pear-shaped aluminum nose, at- nitrate acts not only as a non-hydroscopic and
tached to the forward end of the snake in such a non-corrosive oxidizer and extender for TNT but
way that the nose can sw ivel slightly, aids in also as a substance which improves the propaga-
guiding the snake over and around obstructions. tion of the detonation wave of TNT, Baratols
Other components and accessories adapt the are not as efficient expls as amatols(on a wt
snake for pulling or pushing by a tank. One hun- basis), but on a vol basis there is practicably no
dred twenty-eight demolition charges M2 are used difference
with each M3 snake, 400ft long. Each charge M2 Originally there were the following two form-
is elliptical in shape and weighs 401bs including ulations for B aratols:
ca 351bs of expl, which is 80/20 amatol with a a) 80/20 Cold Mixed Baratol (Brit nomenclature),
booster chge of crystalline TNT at each end. The c ailed 20/80 Baratol by the US nomenclature. It
chges are loaded in 320ft of the 400-ft snake, contains 20*2.0% B a nitrate [ freshly ground to
giving an expl wt of 14 Ibs per loaded foot. pass the BSI(qv) sieve No 60 and dried to a moist
Dirt-filled tamping bags are placed adjacent to the content not higher than O. 1%] and 80i 2.0% TNT
charges and extending 10ft toward the nose of the (ground to pass the std BSI sieve No 25). This
snake and 20ft toward the rear to prevent the Baratol has been prepd by blending of ingredients
chges from shifiing. Loading assemblies for at RT, preferably at the site of the plant where
bangalore torpedoes(see above) may be used as filling of ammo with Baratol takes place. Load-
an alternative expl charge. Two fuzes, bullet im- ing of ammo can be done either by hand stemming
pact, Ml are supplied with each demolition snake. or by direct pressing. The prepd Baratol shall
Total wt of this snake is ca 9 tons including all pass No 8 BSI sieve and at least 75% to pass
4.5 tons of expls(Ref 5,P 289) No 25 BSI sieve. Moisture content must not ex-
Refs: l)Anon,WarDept Field Manual FM ~ 1 ceed 0.10%. NO grit, visible impurities or foreign
( 1944-5),psts 46.02 to 46.05-i la)Anon>{Ammu- matter must be present
nition Inspection Guide’, TM 9*1904( 1944), 270-1 b)90/1 O Poured Baratol,(Brit nomenclature), cal-
2)Ohatt( 1946),375-6 3)Anon, ‘Complete Round led 10/20 Baratol by US nomenclature. It contains
Charrs’5981,0RDIM, ~C0,W’ashin8ton DC(1950), 10+1.0% Ba nitrate(ground to pass the BSI sieve
sheet 454 )C.E .B all, The Town Journal, April No 72) and 90tl .0% TNT(Grade 1 or 2). Its prepn
1955,P66 5)Anon, ‘Ammunition General’) TM 9* is as follows:
190U 1956), 266-7 & 286-9 6)E.J.Murray & S*J. A freshly ground Ba nitrate is gradually added
Lowell,PATR 2297(1956) (Conf) (Development Of while stirring to molten TNT, preheated to 90°,
improved expl chges for Bangalore Torpedoes not allowing the temp to drop below 85° during
MIA1 & M1A2 and Demolition Snake M3 ) 7) CInfor- mixing. The mixt is cooled while stirring to the
mation Rept of the Central Intelligence Agency’, consistency of ‘porridge’ and poured into suitable
NO CS-LT-K-RC-383 1,4 Dec 1956( conf) 8)PATR molds to be solidified in slabs of ca 1/2” thick-
251O(PB No 161270 )(1958),P Ger 115 9)US Spec- ness. The slabs are broken into pieces suitable
ification MIL-T-1339(Ord)~ Bangalore Torpedo in size for biscuit(pellet) loading of ammo. The
MIA1 10) Dr Hans Walter, PicArsn,Dover,NJ; d of the slabs should be about 1.63 to 1.68. Any
private communication 1 l)A. B. Schilling,PicArsn; pieces showing spongines~ are discarded. An-
private communication 12) ’Ammunition Complete other method of loading consists of pouring the
Round Charts’,Book III, Ordnance Ammunition *porridge’ into components in one or more incre-
Comman~Joliet,Ill,15 Ott 1959, Chart 22 13)US ments. Before a 2nd or subsequent pouring is
Specification MIL-T-2087 14)US Specification made, the shrinkage cavity from the previous
MIL-C-14003A,Cap, Blasting, Special, Nonelectric pouring is broken through. Final toppings may be
(Type 1) and Cap, Blasting,Special, Electric(Type made by pouring the Baratol melt mix directly at
2) (formerly known as Cprps of Engineers Caps) 85° without allowing it to cool further in the
(See aLso this volume under BLASTING CAPS) melt pot. The props of 90/10 Baratol (British)
were reported in Ref 2 as follows: color-buff;
BAR. Browning Automatic Rifle. See under Brown- density o{ loading ca 1.65; WIP 80-5°; brisance (by
ing’s Weapons sand test)- 36 g sand grushed, vs 43 g for TNT;
(relative brisance 84% TNT); detonation veZ-
Baratol is an expl compn contg Ba nitrate & TNT ocity -5900 m/see at d 1.65, vs 6900 for TNT;
in various proportions, developed by the British corrosivene ss-ntm-corrosive; bygfos copicity-non-
and used during WWII. It was claimed that Ba hygroscopic; impact sen.sitivity-12” vs 14” for TNT

—
on PicArsn App with 2-kg wt; power(by Trauzl clude detn of moisture content(max alIowable
Test)-98%TNT,(by BalIistic Mortar} 98% TNT; 0.25%) and detn of composition. For the moist
rifle bullet sensitivity-20% detonations from .30 content, a 5g sample of pulverized material in a
cal bullet shot from a distance of 90fC stability shallow dish is kept in vacuo over coned suJfuric
(therm aI}as stable as TNT; uses-as bursting acid for 18 hrs and then reweighed. The moisture
chge ia depth bombs, A/T(antitank) mines and free material is transferred to a Gooch crucible in
some grenades which it is extracted with hot, dry benz until
As both the above Brit Baratols have highly free of TNT. The crucibIe with residue is dried
negative oxygen balance to C02 (-53.1% for 80/ at 100° for 1 hr, cool ed in a desiccator and re-
zo and -65.5% for 90/10 Baratol) (the method for weighed(Ref 3)
calculating OB of a mixt is described under Bar- Refs: l)Thorpe 1(1937),619 & 4(1940),464
onal) two new formulations contg much higher per- 2)AIl&EnExpls( 1946),89-90 and table,p 57
centages of oxidizer(B a nitrate) were developed 3)US Military Intelligence Division Reports
in the US. One contained: Ba nitrate 73 & TNT R-979-51 & R-1149-51(1951) 4)PATR 17~,Rev 1
27%(OB to C02 + 2.lz *d to CO + 15.6%), while (1958)
the other consisted of Ba nitrate 67 & TNT 33%
(OB to C02 is -4.2% and to CO+ 12.1%). The Barbarit. A Ger chlorate expl formerly manufd by
latter compn, called 67/33 Baratol in US and the Sprengstoff-F abriken Kriewald bei Gleinitz:
33/67 Baratol in Gt Britain, is still in use and K chlorate 90-92 & high boiling petroleum fraction
its props are as follows: booster sensitivity 100g 10-8%. Flash point of petroleum was required to
Tetryl detonates cast” Baratol in 50~ of trials be not below 105° and boiling point not below
through 0.32” of wax; brisance(by sand test)- 242° Re/:A.MarshaIl, ‘Dictionary of Explosives’,
26.8g sand crushed vs 48.Og for TNT(relative Churchill, London( 1920),12-13
brisance 56?% TNT); density (cast) 2.55; ex-
plosion temperature- ignites at 385° in 5 sees; Barbe first name or initial given) proposed in
Hygroscopicit y- nil at 30° & 90%RH; impact sen- 1883 to diminish the sensitivity of NC by incorpo-
sitivity 35cm vs 90-100cm for TNT(BurMines App, rating organic or inorganic nitrates, preferably
2kg wt} ll”(sample wt 24mg) vs 14” for TNT AN. The same inventor proposed in 1885 to dimin-
(PicArsnApp, 2kg wt); power - not given in refs ish the hygroscopicity of AN and to assure its
listed beIow; sensitivity to initiation - ().d()g of neutrality by incorporating some Amm carbonate
Bsratol require a detonator contg 0.20g LA & Refi Daniel(1902),56
O. 10g Tetryl(Ref 5)
Preparation of 67/33 Baratol. The approx wt of Barbette. A mound of earth or a specially pro-
Ba nitrate, preheated to ca 90°, is added to molten tected platform on which guns are mounted to fire
TNT contained in a melting kettle equipped with * over a parapet; a cylinder of armor on a warship
agitator. Mixing is continued until a uniform mass that gives protection to the rotating part of the
is obtained. Then the melt is cooled slightly while turret below the gunhouse; a fixed superstructure
on an armored vehicle, usually with gun mount of
the agitation is continued and is loaded into ammo
at the lowest temp at which it will flow freely(Ref 4) limited traverse
Refs: l)F.W.F.Gleason, ArOrd 31, 369(1947)
Analytical Procedure Used at Picatinny Arsenal 2)Merriam-Webster’s (1961) 175
for Baratol( as described in CLR 121813).
Transfer an accurately weighed sample of ca 2g Barbituric Acid or Malonylurea
dry Baratol to a 400ml beaker. Add 200M1 of dry f t
HN.C0.NH.C0.CH2 .CO; mw 128.09, N 21.87%; wh
benzene and allow the mixt to digest on a water-
trysts, mp 245°. Its mono-Na salt was proposed as
bath for lhr. Transfer quantitatively the in sol
a component of composite AN propellants(see under
portion to a large tared sintered glass crucible
Combustion Catalysts for Composite PropInts)
(which has been previously washed with benz
Refi Beil 24,467,(410)& [267]
and dried at 100t2° for lhr) and wash its contents
with four 25ml portions of benz, aspirating each BARC. See under Amphibian Vehicles, in Vol 1,
time until most of the benz is removed. Dry the p A678-L of this Encyclopedia and the article of
crucible at 100*2° for lhr, COOI in a desiccator H. A. Jacobs in Ordnance 38,529-31(1953)
and weigh. The wt of residue is Ba nitrate
Analytical Procedures Used by the British in- Barisutaito. J ap for Ballistite
 B 20

Barium ,Ba, at wt 137.36; silvery metal, d 3.5mp Barium Hexanitride. Same as Barium Diazide
850°, bp 1140°; attacked by w and by ale. Can be
prepd either by electrolysis of fused salt(such as Barium Hydride. See under Hydrides
Ba chloride) or by the reduction in an evacuated
retort of a Ba compd(such as oxide) with Al at Barium Hydroxide. See under Hydroxides
1200° or higher. Used in many alloys. Lenze &
Metz(Ref 2) investigated explns produced on Barium Hypochlorite. See under I-Iypochlorites
heating mixts of metallic Ba with organic halogen
compds, such as t etrabromome th ane, tetrachloro- Barium Hyposulfite. Same as Barium Thiosulfate
ethane, etc. They also detd the sensitivity to im-
pact, Trauzl test values and some other props of Barium Iodate. See under Iodates
such mixts
R e/s: 1 )Mellor 3(1923),620-49 2) F. Lenze & L. Barium Iodide. See under Iodides
Metz,SS 27,257-8,294 & 337-8( 1932~ CA 27,844
(1933) 3)Gmelin,Syst Nr 30,Hauptband(1932), 1-7 Barium Nitrate(B aN) (Nitrobarite)(B arytsalpeter,
and Erg%nzungsband( 1960),1-272 4)Thorpe I (1937), in Ger), Ba(N03)z, mw 261.38, OB to BaO & N
631 5)Kirk & Othmer 1( 1947),462( undet Alkaline +30.6%. Col cubical & octahedral trysts, d 3.244
Earth Metals) 6)Giua, Dizionario 1(1948 ),625-6 at 23°, mp 592°, bp dec;no 1.572; sol in w(5.02g
7)Ullman 4(1953 ),171-2 in 100g w at 0° and 34.2g at 1000); SI sol in acids;
insol in alc & in eth. Can be prepd either by
Barium Acetylide. See Vol 1,p A70-R of this treating native carbonate(witherite) or the sulfite
Encyclopedia with hot dil nitric acid, followed by crystn; or by
double decompn of BaC12 with Na nitrate(such as
Barium Azide. See Barium Diazide in Vol 1 Chile saltpeter) in hot aq soln with subsequent
p A523-L pptn of BsN
When heated above 800° BaN decomp into B aO,
Barium Bichromate. Same as Barium Bichromate N & O. It has been used as an oxidizing agent
in composite expls, proplnts, & pyrotechnics as,
Barium Boride. See under Borides for instance, in Baratol, Baronal, Brugere(Poudre),
Tonite, detonators, fuzes, primers, etc. One of
Barium Bromate. See under Bromates the Jap expls used during WWII in boosters for de-
molition charges contained: B aN 34.5, NH4C104
Barium Bromide. See under Bromides 51.5, oil & trinitronaphthalene 8.2, woodpulp
5.o & other ingredients 0.8%(Ref 5,P 32). A RUS
Barium Carbide. See Barium Acetylide, VO1 1, thermite-type incendiary compn, press-loaded in
p A70-R 76mm shell s, contained BaN 44,K nitrate 6,
Fe304 21, Al 13, Mg 12 & binder 4%(Ref 10,p210).
Barium Carbonate. See under Carbonates Mixts contg BsN are slower burning than those
contg K nitrate and the ignition points are higher.
Barium Chlorate. See under Chlorates The advantage of BaN over AN is its non-hygro-
scopicity
Barium Chloride. See under Chlorides Since Ball has the property of emitting green
light when heated, it has been used in signal
Barium Chromate. See under Chromates and flares, signal rockets, stars, railroad torches,
Dichromates tracer compns and some compns producing white
light
Barium Diazide. .See Vol l,p A523-L Following are some examples: a)BaN 60,K
perchlorate 18, Na oxalate 9, shellac 9 & sulfur
Barium Bichromate. See under Chromates and Di- 4%; used in signal torches(Ref 8,P205) b)BaN 50,
chromates. Several pyrotechnic compns contg K chlorate 35 & shellac 15%; used in green stars
BaCr04 are described by H. Ellern,%iodern Pyro- (Ref 8,p211) c)BsN 39, K chlorate 39, ch=coal
technics’,Chem Publg C0,NY(1961), 283-4 13, shellac 6 & gum arabic 3%; used in green
stars(Ref 8,p211) d)BaN 53, K chlorate 31, sulfur
Barium Fluoride. See under Fleorides 10 & charcoal 6%; used in green signals(Ref 8,
 B 21

p211) e)BsN 74-80&Al 36-20; used in tracers Barium Picramat% See VOI l,p242-L of this
(Ref 8,p220) f)BaN 57, Al 30, Sb trisulfide 6, cry- Encyclopedia
olite 6 & castor oil 1%; used in Ft signal cartridg-
es, type Vi%y(Ref 8,p226) h)BaN 55, Mg35 &bind- Barium Picrate. See under Picrates
er lo%;used in white tracers(Ref 10,p181) i)BaN
52, Mg 40, K oxalate 6 & binder 2%; used in white Barium Resinate, See under Resinates
tracers(Ref 10,p 181) j)Various pyrotechnic
compns listed by Ellern(Ref 13) Barium Stearate. See under Stearates. Its use in
US Military requirements for BaN are given in smoke-producing compns was patented by J.
Ref 11, Russian specification requirements are DeMent, USP 2995526( 1961),p6
listed in Ref 10,P 29. Detn of Ba nitrate in
proplnts is described in Ref 12 Barium Sulfate See under Sulfates. A white flare
Re/.v: l)Mellor 3(1923),849-64 2)C.A.Taylor & compn contg BsS04 is listed by H. Ellern, ‘Modem
W.M. Rinkenbach, ‘Explosives’, USBurMinesBull Pyrotechnics’, ChemPublgCo,NY( 1961),274
219(1923),21-25 3)Gmelin,System Nr 30,Haupt-
band(1932),149-64 & Ergknzungsbmd(1960),305- Barium Sulfide. See under Sulfides
16 4)Thorpe 1(1937),639 & 4(1940,464 5)Anon,
‘Handbook of Japanese Explosive Ordnance’, Op Barium Superoxide, Same as Barium Peroxide
Nav 30~3M GovtPrtgOff,Washington,DC( 1945),32
Barium Tetrazidocuprate, Ba[Cu(N3 )41, a complex
6)Kirk & Othmer 2(1948),315 7)Giua,Dizionario
salt exploding at 208-9° is described by M. Strau-
1(1948 ),628-9 8)Izzo,Pirotecnia( 1950),205ff
manis & A. Cirulis, Z Anorg Chem 252,9-23(1943)
9)Ullmann 4(1953),178 10)Shidlovskii Pyrotech-
& CA 38,3564(1944)
nics(1954),22,27,29,149,181 & 210 1 l)US Military
Specification MIL-B-162B 12)Military Standard Barium Thiosulfate. See under Thiosulfates
MIL-STD-286A(1956) Method 304.1.2 13)H,Ellem,
ldodern Pyrotechnics’, ChemPublgCo,NY( 1961), Barlow Bomb. According to John M. King, formerly
272-8, 284 of PicArsn, Barlow proposed ca 1936 a mixt of
liquid oxygen with a fuel(such as charcoal) as a
Barium Nitrate Mixtures, Analysis. See Vol l,p bursting chge for bombs. This expl mixt was test-
A586 of this Encyclopedia ed sometime before WW11 at Aberdeen Proving
Ground and was found to be not as effective as
Barium Nitride, Hexa. Same as Barium Diazide TNT

Barium Nitrite. See under Nitrites BarnwelI & Rollason(no initials given) patented
in 1860, in England, modified black powders in
Barium Nitrominoguanidine. See Nitroaminoguani- which part of the charcoal was substituted with
dine(NAGu) Salts, under Aminoquanidine in Vol 1, NC. Such powders could be prepd by mixing K
p 212-L of this Encyclopedia nitrate, sulfur & charcoal with soln of collodion
cotton in ether & alcohol and then evapg the
Barium, Organic Salts of. See under individual soIvent
organic compds Re/: Daniel( 1902),57

Barium Oxalate. See under Oxalates Barometric Fuze See under Fuzes.

Barium Oxide. See under Oxides Baron & Cauvet Explosives. See Cauvet & Baron
Explosives
Barium Perchlorate. See under Perchlorates
Baranal. A composite expl: Ba nitrate 50, TNT
Barium Permanganate. See under Permanganates 35 & Al 15%, developed in the US during WWII as
a cast able filler for underwater mu nitions(Ref l).
Barium Peroxide. See under Peroxides. A white It was hoped that Baronal WOUI d be much less
tracer compn contg Ba02 is listed by H. Ellern, sensitive than the British Torpex-2(42/40/18
‘Modern Pyrotechnics’, ChemPublgCo,NY( 1961), RD x/TNT/Al) but this proved not to be t~e and,
276 as Torpex-2 was more powerful, it was adopted
 f

B 22

as an underwater charge(Refs 1 & 2) 100*2° for lhr, cool in a desiccator and reweigh.
Baronal can be prepd by heating TNT to ca 90° The loss in wt is equal to BaN, while the
and adding, whiIe stirring, preheated pulverized residue is equal to Al(Ref 6)
BaN & AI powder. Following are the props of Refi l)D.P.MacDougall, OSRD 1035(1942)
Baronal: OB to C02,H20,Ba0 & A1203 -23.9%; 2)NDRC, Summary Technical Rept of Div 8, Vol 1
OB to C0,H204 BaO & AL20 ~ -6.7%( see note (1946), 33 3)Allied & EnExpls(1946),85 4)W.G.
below); booster sensitivity IOOg Tetryl detonates Penney et al, ProcRoySoc A204, 14( 1950) (De-
cast Baronal in 50% of trials through 0,86” of wax; tonation rate of Baronal ) 5)PATR 1740, Rev 1
brisarrce(by Sand Test) 39.8g sand crushed vs (1958) 6)C.Ribaudo,PicArsn; private communi-
48g for TNT; density (cast) 2.27-2.32; detonation cation(1960
rate 545o m/see at d 2.32 & chge diam 1“; ex-
plosion temperature 345° (ignition in 5 sees); Barrage, Balloon. See Balloon, Barrage
heat of combu.stiorz(Q c) 2099 cal/g; heat o/ ex-
plosion (Qe) 1135 cal/g; beat o/ /oration 41o Barrel, Erosion of. See Erosion of Gun Barrel
cal/g; bygroscopicity nil; impact se nsitivity
30cm(BurMinesApp, 2kg wt) vs 95-100cm for TNT Barrel Finishing is described in the “~andbook
and 12” (sample wt 22mg)(PicArsnApp, 2kg wt) of Barrel Finishing”, by R. Enyedy,ReinhoId,NY
vs 14” for TN T; power(by Ballistic Mortar Test) (1955)
ca 90% of TNT; sensitivity to initiation 0.40g of
Baronal requires a detonator contg 0.20g L A & Barrel, Gun (or Tube). The cylindrical metallic
O. 10g Tetryl part of a gun which controls the initial direction
Principal use o f Baronal is for filling bombs, of the projectile. The term tube is preferred for
but it also can be used as replacement for Al- designating the 1arger diam barrels(See also Bore)
umatol, Ammonal, etc Refi Glossary of 0rd(1959),32
Note: In Vol l,p A515 of this En cyclopedia is
described a method for calcn of oxygen balance Barrel (or Bore)OsciIIations (or Vibrations)
for individual compds, but nothing is said about (Laufschwingungen in Ger). In the course of
calcn of OB’S for m i xtures. The simplest firing a projectile, the gun barrel does not re-
method is to proceed as follows: a) Calculate main stationary but oscillates somewhat, being
OB’s of individual components and divide the especially pronounced at the muzzle <end of the
values by 100 b)Multiply each OB by the corre- barrel
sponding percentage in the m ixture and then add C .Cranz & K. R.Koch designed, in 1896, an
the resulting values apparatus which permits registering by high-speed
Taking Baronal as an example, we have OB photography, the vertical as well as the horizon-
for BaN to BaO = +30.6%, for TNT to C02 & tal oscillations of a gun barrel. The same ap-
H20 = -73.9% and for Al to A1203 = -88.9%. paratus takes pictures of the projectile as it
This gives for 50/35/15 -Baronal: 50x 0.306 + leaves the muzzle
35x( -Q739) + 15x( -0.889) = -23.8%. If TNT goes Refi Cranz 3 (1927)$ 279-281
to CO & H20, its OB is -24.7%, which will give
OB for Baronal: 50 x 0.306 + 35x( -O.247) + 15x Barrel, Racket .A vernacular term for the major
(-0.889) = -6.7% component of a liquid-propellant rocket motor
Analytical Procedure for Baronal. Transfer an wherein combustion takes place; the term tlvwst-
accurately weighed port ion of ca 2g to a 400-.ml cbamber assembly is preferred
beaker. Add 200ml of dry benzene and allow the Re/: Rocket Encycl( 1959),40
mixt to digest on a water bath for 1 hr. Transfer
quantitatively the insol residue to a large tared Barricades in Explosives and Ammunition Instal.
sintered glass crucible (which has been previous- Iations. Barricades are required for protection
ly washed with benz and dried at 100t2°) and of inhabited buildings, factories, magazines, rail-
wash the contents with four 25mi portions of benz roads, highways, bridges, etc from explosions in
aspirating each time until benz is removed. Dry installations in which ezpls or ammunitions are
for lhr at 100t2°, cool i n a desiccator and weigh, manufd, handled or stored. A barricade can be
The loss in wt is equal to TNT. Rinse the either natural(such as a hill or timber of suf-
residue(BaN+Al) with hot distld w until all BaN ficient density) or artificial(such as a sand- or
is removed, dry the crucible with residue at earth-filled embankment with a min width of 3ft
 B 23

at the top). It should be located at a min of 4ft Ibid, DB-TR: 5s57( 195,7 )( Evaluation of vented
from the bldg it is to screen and either one or barricade DP-54711 utilized in handling of ex-
both sides of the barricade may be supported by plosive powders) 13)A.Kush,Ibid, DB-TR: 11*57
concrete, timber or masonary walls. A bldg is ( 1957)( Testing of flue-vented barrit?ade DP-44206
considered to be barricaded(or screened) if the 14)SAX(1957), 154-5 15)Anon, “Ordnance Safety
heights of barricades are such that a straight line Manual”, ORDM 7*224,,Secn 17(1958) 16)Cook
drawn from the top of any sidewall of the bldg (1958 ),354-5 17)B.Kroll et al, PicArsnIndDiv
contg hazard to the cave Iide of any other bldg TecliRept DB-TR: 5@1958)(Barricades)
or to a point 12ft above the center of a railroad,
highway, etc, will pass through the intervening Barrier Creams are used in expls and ammo plants
barricade (Refs 1 & 8) for protecting the human skin from airborne expls
The permitted distances from barricaded bldgs or toxic materials. According to Cumming et al
(called bamicaded distances) to other bldgs, rail- (Ref), a satisfactory barrier cream should have a
roads, etc are enumerated in the ‘American Table softening point of ca 22° to facilitate spreading
of Distances for Storage of Explosives”, as Re- in the layer of ca 20p thickness to avoid penetra-
vised and Approved by the Institute of Makers of tion by airborne tetryl crystals of ca 5p in size.
Explosives, Sept 30, 1955. This table is given in The so-called Cambraild Barrier contg paraffin
Refs 14,15 & 16.. .~istances shown in this table wax(mp 135°F) 20~ vaselin 40, Ianette wax(as
should be doubled if dangerous bldgs are not emulsifying agent) 10 & water 30% is considered
barricaded satisfactory because when applied to the skin it
Igloos, when protected by a barricade at the protects it for ca 6hrs from airborne TNT or Tetryl
door end, are considered to be barricaded in all particles. incorporation of 2% boric acid and other
directions and barricaded distances may be used solids impairs the efficiency of the above barrier.
as minimum safe distances in locating them from Lanolin and most vegetable oils and grerises are
other magazines, operating or inhabited bldgs, considered unsuitable as barriers because many
railroads, etc. Where igloos are not barricaded expls (TNT, P.A, RDX, etc) dissolve in them
at the door end, the istances in~egard to the Refi W.M.Cumming et al, BritJIndMed 4,237-41
f
bldgs iocated within the area bounded by lines (1947) &CA 42,2429( 1948)
drawn from the door of the igloo and inclined by
30° from a line drawn perpendicular to the front Barrier Materials may be defined as substances
of the igloo should be double those given in the designed to withstand, to a specified degree,
table of Refs 14,15 & 16. Such distances are penetration of water(liq or vapor), certain gases
called unbarricaded distances (as desired), oils & greases. Barrier materials
The work on standardization of barricade de- may serve to exclude or retain such elements
sign and on testing of various types of barri- without or within a package. These materials
cades conducted at picArsn by Industrial Di- (especially the flexible types) are used now ex-
vision is described in Refs 3-7,10-13 & 17 tensively in all types of military packaging
Re/s: I)Anon, ‘Ammunition Inspection Guides, There are four major types of barrier materials
TM 9*1904(1944),799-801 2)C.Field et al, =Bar- used now in the US for military purposeTs: a)Water-
ricades”,Naval Prooving Ground, Arco,Idaho( 1945) proof b)Greaseproof c)Water-vapor-proof and d)
3)B.Kroll & A.Kush,PicArsnIndDivTechReptPED Combinations o{ a,b & c. Almost all the barrier
50~~l(1953)(Standardization of barricade design) materials in use today are composed of several
4)Ibid,PED=50!~2( 1953) 5)R.Flohr & A.Kush, layers or plies. “The plies are usually cemented
Ibid,PED=50 I*3( 1954) 6)A.KUSWMPEW501“4 together with suitable adhesive s(latninants) to
(1955) 7)S.Wisneski,Ibid, PED-fiOl*6(1955 )( Ef- form a laminated structure, although several other
festiveness of safety glass as shield barricade methods of making multi-ply sheets are also
material) 8)Anon, ‘Military Explosives”, TM 96 used. Materials used for making plies include:
19 IO( 1955),303-4 9) Anon, ‘Care, Handling, Pre- kraft paper, cotton scrim, aluminum foil, poly-
servation and Destruction of Ammunitions, TM ethylene, cellulose acetate, Mylar, etc
9t1903(1956),35-7 10)S.Wisneski & A. Kush,Pic A description of flexible barrier materials used
ArsnIndDivTechRept PD-50 1-7( 1957 )( Relative in military packaging is given in the lecture of
effectiveness of barricade window material and Weiner(Ref 1)
support area) ll)A.Kush,Ibid,PD-50 1“9(1$M7) US military requirements and tests for barrier
(Standardization of barridade design) 12)A.Kush materials are covered by severrd specifications
 1

B 24

which are listed in Ref 3, of-which the Specs some semifixed ammo), it .is usually devided into
MIL-B-121B and MIL-B-13239B are the most a number of bags corresponding to the zones of
frequently used byth~ Army fire. The principal chsrge(usually the largest),
MIL-B-121-B covers flexible, greaseproof, water- which corresponds to zone 1, is called the base
proof barrier material, for the protection of mili- charge and is inserted closest to the primer.
tary supplies and equipment during transportation Additional charges are called increme~s. For
and storage under all climatic conditions, while the longest desirable range the charge consists
MIL-B-13239B covers flexible, waterproof, all of a base chge and all t he increments and if
temperatures barrier materials of several rypes, shorter ranges are desired, one or several in-
such as bailing, case liners & wrappers, interior crements are removed from the gun prior to
wrapping, materials for interior ”packaging bags, firing
and temporary tarpaulins Re~s: l)Hayes(1932),32-3 2)Ohart(1946), 181,
MIL-B-3959 covers barrier materials for moder- 184 & 192 3) Anon, “Ammunition General”, TM
ately water-vaporproof interior packaging bags. 9-1900( 1956),130-1
It is also used by the Army
Spec MIL-B-13 lC, covering barrier materials, Base Cover (also called Base Plate). Since the
water-vaporproof, flexible, is used mostly by material used for the manuf of shell bodies(cast
the US Navy steel and sometimes cast iron) can be in some
Refs: l)H.M.Weiner, aFlexibl e Barrier Materials cases porous, there is a possibility that the hot
in Military Packaging”, A lecture delivered at gases of propellant chges in artillery weapons
PicArsn in March 1954 2)Packaging Institute, might penetrate through the bottom and either
Inc, ”Glossary of Packaging Terms”, NY(1955),31-2 ignite or detonate the contents of the shell,
2a)R.H.Devore,”Long-Term Storag Tests of Bar- which can be either chemical or HE. In order to
rier Material s”,PATR 2121(1955) (Conf) prevent direct contact of hot gases with the
3)”Index of Specifications and Stand ards(Used by bottom of the shelI, the following methods have
Department of the Army”, vo12(1959), 14 4)G.R. been used: a)For weapons of ca 75mm to ca
Rugger & Betty Garnis, PicArsn;private com- 155mm, the base is protected by a steel disc
munication 1960) soldered or welded to the base or by a sheet
brass disc brazed to the base(Refs 1 & 2 and Ref
Baryte. Fr for Barium Nitrate 3,PP 5,9,12,13 & 220) b) For larger caliber weaP-
ons(such as 155mm add up), the base cover as-
Baryte (Dynamites). IJnder the title, Dynamites 2 sembly consists of a shal low copper cup placed
la baryte, Daniel(1902),57, describes the follow- over a lead disc. The cup is held in a dove-tailed
ing dynamites proposed by A. Nobel: Nol:BaN groove in the base of the projectile by means of
65.21, NG 21.74 & charcoal 13.05% No2:BaN 70.0, a strip of lead talking wire which is hammered
NG 20.0 & resin 10.0% down to fiil the groove completely and to bend
the flange of the copper cup. This type of cover
Baryte (Poudre) was, according to Daniel(1902), is called talked type base cove4Ref I,p 559;
57, a mixt of BkPdr 80 & Ba nitrate 20%. It was Ref 2,p 110 & Ref 3,pp 29 & 212)
used in Germany ca 1865 in large caliber guns Note: As the metal in current cast steel or cold
extrwsion shells is less porous than heretofore,
BAS. A cast double-base proplnt developed at there is a tendency to eliminate base covers,
ABL. Its compn & props are in conf “Propellant especially in smaller caliber shell s(Ref 4)
Manual”SPIA/M2( 1959),Unit No 456 (See also Base Plate)
Re/s: l)Hayes(1938),554, 559, 562 & 564 2) Ohart
Base. See under Acid and Base,Vol l,p 87-R of (1946 ),98-9 & 110 3)Anon, ‘Artillery Ammunition” ~
this Encyclopedia TM 9~1901(1950). 5, 9, 12, 13, 29) 212 & 220
4) A. B. Schilling,PicArsn; private communication
Base Charge of a Detonator. See under Detona- ( 1960)
tors
Base Detonating Fuze. See under Fuzes
Base Charge of a PropelIant. When a proplnt chge
is loaded in bags(as in separate-loading and Base Election Smoke SheIl. See under Smoke Shells
 B 25

Base ignition Smoke Shell. See under Smoke Shells ed the use as components of primary compns the
basic lead salts of picric acid, trinitrocresol,
Base of a Projectile is the part of the projectile hexanitrodiphenyl amine, di- & tri- nitroresorcinol,
aft of the rotating band trinitroorsinol, di- & tri- nitrobenzoic acids,
Re/s: l)Hayes( 1938),559 2)Anon, “Artillery trinitrophloroglucinol, tetranitrophenol, nitrated
Ammunition”, TM 9~ 1901( 1950),8 sminpphenols, dinitronitrosoben zene, pol ynitro-
naphthols and mono- & tri- nitromethane. R“ath sburg.
Base Plate usually refers to a thick metallic & Friederich (Ref 2) patented the use in detonators
threaded disc which serves to close the rear con- of basic mixed lead salts prepd by treating a sol
ical section of a bomb after loading(Ref 1). The salt of tetrazole or its derivs with a soln of a SOI
same disc is called body plug in Ref 2 salt of one of the above mentioned compds(such
Refs: l)0hsrt(1946),217 2) Anon, ‘Bombs for as picric acid), followed, by running the mixts
Aircraft”, TM 9-1980(1950),35 into a hot soln of Pb acetate
Re/s: l)W.Friederich, BritP 192830( 1921) & JSCI
Base Plug usually refers to a thick threaded 42,332A( 1923) 2)H.Rathsburg & W. Friederich,
metallic disc used for cIosing the base section BritP 195344( 1922) & JSC1 42,804A( 1923)
of a shell after loading it from the reartcompsre
with Base Plate and with Base Cover) Basic Lead Styphnate. See under Resorcinic Acid,
Re/s: l)Ohsrt( 1946),106 2)Anon, “Artillery Am- Trinitro
munition”, TM 9~1901(1950),9,12 & 13
Basic Lead Styphnate, Mixtures, Analysis. See
Bases Used in the Manufacture of Explosives Vol l,p A586
and Prapellants. Following are a few examples
of bases used in expl plants and labs: a)ca Basic Measurements. Under this term are included
hydroxide has been used as a catalyzer in some the measurements of length, mass, surface, vol-
reactions and as neutralizer of acidic w asaes ume, time, etc
from plants manufg acids, TNT, etc b)Ammoniu Refi J. Reilly & W. N.Rae, “Physico-Chemical
hydroxide- as a neutralizer of acidic materials Methods”, Van Nostrand,NY,vol( 1943),11-73
and as a purifier of crude TNT(such as was prac-
ticed during WW II at the West Virginia .Ordnance Bass. See Bast or Bass
Works). its use in them labs is very extensive
c)Na hydroxide has been used in some plants for Basso Esplosivo(ltal). Low explosive(propellant)
neutralizing acidic subst antes. For inst ance~
red wzters(qv) of TNT plsms are neutralized and Bast or Bass is the fibrous inner bark of linden,
made alkaline prior to their concn in stills. Lab lime and some milkweed trees. It is used for
uses include titrations of acids manufd at the ropes, mats, peasant shoes(such as Rus%qti”).
plants d)K hydroxide has been used in labs of The term blast fiber is applied to fibers obtained
plants for calorimetric testing of TNT and DNT, from the inner bark of flax, hemp, jute, ramie,
et c etc. They contain a considerable amt of cellulose
and can be nitrated to NC. However, these sub-
Bashforth Chronograph. See under Chronographs stances are more valuable as fabric materials
than as sources of NC. Ramie has been used in
Basic Cupric Azide. See Cupric A zide, Basic France for prepn of pure NC
VO1 l,p A533-L, under Azides Refi J. T.Marsh & F. C. Wood, “An Introduction to
the Chemistry of Cellulose”, Chapman & Hall,
Basic Lead Acetate. See Vol l,p A28-R, under London( 1945),1,3 & 12
Acetates
BAT. A cast double-base proplnt developed at
Basic Lead Azide. See Lead Azide, Basic, Vol ABL. Its compn & props are given in conf ‘Pro-
l,p A555-R pellsnt Msnusl”spIA/M2( 1959),Unit NO 457

Basic Lead Salts of Various Organic Nitrqgen Batteries, Electric, Dry are described in Kirk &
Containing Compounds. Friederich(Ref 1) patent- Othmer 2( 1948),324-340(7refs)
 B 26

Batteries, Electric, Storage. See Accumulators and was fired by a magneto arrangement. Its
inVol l,p A12-L of this Encyclopedia rocket(22” long and weighing 6.2 Ibs) carried .a
propellant chge; such as BBP(qv) of 0.4 l~enter
Bautzen (Poudre) consisted of nitrolignin drilled wafers on a central rod) and a shaped
50& Knitrate 50% charge warbead of 1 lb of Pentolite. Its muzzle
Re/: Daniel( 1902),58 velocity was 540 ft/sec and the range 1000yds
The bazooka proved to be very effective against
Bautzener Sicherheitspulver. AGer coal-mine tanks and pill boxes. it also can be used in com-
expl contg not less than 70% AN, not more than bination with chemical and smoke rockets for
15% TNT, the rest being Ba nitrate laying down smoke screens at short range(Refs
Ref: A. Marshall, “Dictionary of Explosives”, 1,2 & 3)
Churchill,London( 1920),13 The current launchers, which can be fired from
the shoulder or from a biped and rear supports, are
Bavarit. A. Ger coal-mine expl: AN 90% together designed for 3.5-inch rockets. There are several
with nitrated naphthalene; charcoal may be added models of such launchers and rockets and their
Re/: MarshaH, Dictionary(1920), 13 descriptions are given in Ref 4
Re/s: I)L.A.Skinner,ArnyOrdn 27,260-63(1944)
Bayberry, Wax, Synthetic. See under Waxes 2)Anon, ArmyOrdn 29,75-7(1945) 3)Ohsrt(~946),
342-3 4)Anon,aRockets”, TM 9* 19~(1958),33-47
Bayen’s Fulminating Mixture, invented ca 1779,
consisted of 1 part pptd yellow mercury oxide BBC. A cast double-base proplnt developed at
and 4-5 pares of sulfur. It exploded with violence ABL. Its compn & props are given in conf “Pro-
when struck with a heavy hammer or when heat- pellant Manual”,SPIA/M2( 1959), Unit NO 458
ed on an iron plate
Refi Davis( 1943),402 BBP or M7(Propellant). NC(13.I-13.35%N) 54.6,
NG 35.5, K chlorate 7.8, c~~n black 1.2 a
Boyon (Poudre), patented in France in 1881, con’ Et centr 0.9%; d 1.68, I(impulse) 130 see, n
sisted of K chlorate, coarse bran & gum srabic (pressure exponent) ca 0.7 & temp coef 0.010.
Refs: Cundill(1889) in MP 5,291-2(1892) 2)Daniel Used in 2.36- & 3.5-inch rockets
(1902),58 Re/s: l)”Summary Technical Rept of Div 8,
NDRC”, Vol 1(1946),101 2)Purchase description
Bayonet. A steel, thrusting dagger or knife-type PA-PD-46(1951) 3)Armament Engineering(1954),
weapon designed to be attached to the muzzle 43(table)
end of a fifle, shotgun or musket. The term is
probably derived from a short dagger ?bayonnette” BBV. A cast double-base proplnt developed at
used ip Bayome, France towards the end of the ABL. its compn and props are given in conf ‘Pro-
15th century pellant Manual” SPIA/M2( 1959), Unit NO 493
Refs: l)C.J.Foulkes & E. C.Hopkinson ‘Sword,
Lance and Bayonetm,MacmiH~,m( 1938) BC Poudre). See under B(Poudre)
2) Anon, ‘Small Arms Mat6riel and ‘Associated
Equipment”, TM 902200( 1949),66-7 3) Encycl BCNL (Poudre). See under B(Poudre)
Britannica 3(1952 ),242-3
BCP Powder, According ,to Daniel( 1902),58, it
Bazooka, also known as Rocket, Antitrd, 2.36- was one of the older Brit proplnts, based on ni-
inch, M6 and Launcher, Rocket, Antitank, Ml was trate. No compn is given
designed in the US in the summer of 1942 as a
one-man, shoulder-operated weapon, firing BD (Poudre). See under B(Poudre)
rockets
The original bazooka consisted of a one-piece, BDI & BDT. Cast doublc=base proplnts developed
elec battery-operated weapon, of the open(at both at ABL. Their compns and props are given i.~
ends) tube type which fired a rocket with a shap- conf ‘Propellant Manual” SPIA/M2( 1959), Unit
ed charge warhead. The launcher was provided Nos 495 & 496
with sights and shoulder frame. The improved
launcher was made in two pieces, weighed 161bs Beaded Powder is the translation given in CA
 B 27

(Ref 1) of the Fr term poudre en perles. It seems Beehive Projectile. See under Projectiles
to be the same as ball powder, also called
spherical powder (poudre sph~rique, in Fr)(Ref2) Beeswax or ‘B”Wax. See under Waxes
Refs: l)J.Fauveau & R. Delpy,MP 35,161(1949)&
CA 46,11686(1952) (A new process for coating Beet Pulp Dynamite. A gelatin dynamite contg
“beaded” powders in order to improve their pro- dried beet pulp, was patented in 1928 by C. D. Pratt,
gressivity) 2)J.Fauveau & J. Chausson,MP35, USP 1658816 & CA 22,1477(1928)
175( 1953) & CA 49,12832(1955) (Superficial treat-
ment of spherical proplnt in liquid media) Behavior Towards Heat Tests. See Sensitivity
to Heat, Flame, etc; VOI l,p XXII
Beam. Rider Guidance Systems for Missiles are
described by A. S. Locke, ‘Guidance”, Van Nostrand Bei lstein, Friedrich K- (1838-1906), known for
NY(1955),574-83 the monumental work ‘Handbuch der Organischen
ChemieW, contg info on nearly all known organic
Oeano. Designation of a spherical hand grenade compds. Publication was initiated in 1881 as one
Re/:NDRC Summary Rpt,Div 8, Vol 1(1940),153 volume. Since that time, it haa grown to nearIy
100 books as a collective work. Beilstein was
Beating or Pulping(PiIage, in Fr) of Nitrocellulose born in Russia of German parentage and became
See under CeIfuIose, Nitro, Manufacture professor of chemistry in 1866(when he was only
28 years of age) at the St Petersburg Institute of
Bebie, Jules( 1877-1956). A professor of Chem Technology, succeeding D. LMende16ev. He re-
Engrg at Washington Univ, St Louis, Mo and tired after 30 years and went to Germany to de-
author of the book ‘Manual of Explosives, Mili- vote his time to writing the “Handbuch”. Three
tary Pyrotechnics, Chemical Warfare Agents” and editions came out during his lifetime. He was
of severaI papers on prepn of expls and NC. Born SISO the author of 88 scientific papers, mostly in
in Switzerland, he studied in Germany under G. the field of organic chemistry
Lunge. Collaborated with E.Berl & G. Lunge Re/s: 1)0. N. Witt,JCS 99,1646-9(1911) 2)E.J.
Refi l)J .Bebie; private communication 2)A.non, Moore & W.T. I-fall, ‘A History of Chemistry”,
ChemEngrgNews 34,3364(1956) McGraw-Hill,NY( 1939),309-10

Becco Chemical Div, Faod Machinery & Chemi~ BEJ. A cast double-base proplnt developed at
cal Corp, Buffalo 7,NY, manufacturers of hydro- ABL. Its prepn & props are given in conf Propel-
gen peroxide, peracetic acid, urea peroxide ahd lant Manual SPIA/M2( 1959),Unit NO 514
several other peroxides as well as sodium per-
borate and other chemicals used in proplnts & Beken Mixer, manufd by the Bramley Machinery
expls Corp,Edgewater,NJ. it is a batch-type mixer
Re(: Thomas Register of American Manufacturers, unique primarily in the design and action of ite
NY,vo1 4(1960),98 two mixing padd~es
A pilot scale evaluation of a 15-gallon Beken
Becker, Karl(1879- 1940). Artilfary General, one DupIex Mixer for propeIf ant manuf, conducted at
of the outstanding German balIisticians. The PicArsn, indicated that it can be successfully
Peenemiinde Research Center, where V-1, V-2 substituted for other mixers, such as a sigma
and many other missiles were developed$ was blade mixer
constructed under his guidance in 1937-8 Refi K. H.Russell, ‘Evaluation of Beken Mixer
Refs: l)K.Justrow,SS 35,1-2(1940) 2)Oberst Karl, for Propellant Manufacture”, TechReptDB-TR:
SS 35121-3(1940) (Obitutiy and short biography) 7*59,1ndustrial Engineering Division, Picatinny
3)L.H.Thomas,JChemPhys 12,449-53( 1944) & Arsenal, Dover,NJ ,May 1959
CA 39,621(1945) mote on Becker’s theo~ Of the
shock frorit) 4) F. Rosss JG “G~ded ‘issiies: Belaya Sines’ (White Composition). A Rus per-
Rockets and Torpedoes=, Lothrop,NY( 1951),22 cussion compn: MF 80-85 & K chlorate 20-15%
Refi ShilIing (1946), 97-8
Beehive D~molition Charge. See under Demolition
Charges Belgian Ammonium Nitrate Gelatin Dynamites,
See Vol l,p A368(table)
 B 28

Belgian Control Tests for Explosives. Under the at 18-22° inside a zinc-lined box provided with a
title CEssai de Contr?ile cles Explosifs”, Dr. L. tight-fitting cover, a grating at the bottom and a
Deffet described in “Chimie et Industrie”, Special layer of water. Prior to being submitted to the gap
Number (1950),pp 445-9, devoted to the 21st Inter- test, the cartridges are reweighed to det the amt
national Congress of Industrial Chemistry at of absorbed moisture
Bmxelles( 1948), the tests used in Belgium. These Note: In the opinion of Dr Deffet, tests A, B & C
tests include the safety tests conducted by the do not suffice because they do not det the effi-
“Institut National des Mines” for SGP (S4curit& ciency(rendement) of expls. The efficiency de-
Grisou-Poussi~re) explosives pends on several factors, such as: brisance, pres-
Following is a brief description of these tests: sure of expln, deton velocity, velocity of develop-
Essai A. Puissance(Power test). A 10g sample ment of gaseous pressure and velocity of shock
of expl to be tested, wrapped in tin foil to form wave. As some of these props are difficult, or
a cartridge, is placed snugly in the .cavity(25mm even impossible to det, Dr Deffet proposes to in-
diam and 125mm deep) formed in a lead block clude at least one of these tests, namely brisance
200mm diam and 200mm high. After inserting a among control tests. The method selected by Dr
No 8 electric detonator and tamping with sand, Deffet is the Kaslt Te&,8 in which the compression
the cartridge is exploded. The vol(in cm3) of the (crushing) of a copper cylinder serves as a meas-
cavity after the expln, minus the VOI of the orig- ure of brisance and is described in detail on p449
inal cavity and minus the expansion caused by a o f the above Ref
No 8 detonator(ca 70cc), represents the power of (Description of Belgian laboratories, in which
an expl., Tl@ value divided by the correspondhg these tests are conducted, is given by L.DeH.et
value for PA (picric acid) end multiplied by 100 in the journal ‘ExpIosifs”, BruxelIes, 1959,XII,
gives the relative pozuer(puissance rtlative) 152fl
Essai B, Aptitude ;;! ’explosion (Aptitude to ex-
plosion) or Essai de sensibilit~ (sensitivity test) BELGIAN EXPLOSIVES, AMMUNITION, WEAP-
is conducted somew hat sim ilarly to the American ONS, RELATED ITEMS AND PLANTS MANU-
gap test, which is briefly described in Vol l,p FACTURING THEM.
XIV, under Gap Test Note: For information on this subject, we are in-
In the BeIg test, two cartridges of an expl to debted to the following Belgian scientists and
be tested are attached(in series without an air industrialists: l)Dr L.Def fet, Director of the
gap) to a soft iron rod(4mm diam & 0.5m long) Centre de Recherches Scientifiques et Tech-
by means of thin wires, two pieces to each car- niques pour l’Industrie des Produks Explosifs
tridge. A space of at least lcm must be provided (CRIPE) and the Institute Beige des Hautes Pres-
at one end of the rod(for later attachment of a sions(IBHP) 2)Dr F. Lebrun of the Soci6t6 Ano-
thick wires above and parallel to the ground. The nyme Poudreries R6unies de Belgique(SAPRB) and
first two cartridges are then exploded and if the 3)Mr E.T.omson$ Director of the Fabrique Nationale
thin wires at the other end of the rod leaving a (FN) d’Armes de Guerre, at Herstal-lez-Li~ge
certain air gap betw the end of the 2nd cartridge Although Belguim is a small country, its ex-
and the beginning of the 3rd cartridge. After in- plosives and ammunition industry is quite large
serting a No 8 elec detonator inside the 1st car- and Belgian small arms are famous throughout
tridge, the ensemble ia taken to a special cave the world. Due to extensive mining industry, Bel-
where the rod is suspended from a beam by two gium developed, beginning in the 1870’s, many ex-
#IL4 wires above the parallel to the ground. The cellent coal mining expls. Belgium is also export-
first two cartridges are then exploded and if the ing large quantities of industrial expls to other coun-
gap to the 3rd cartridge is not too great, it will tries. Some good military or civilian expls, propel-
be detonated by influence. The max distance(gap) lants, blasting accessories, arms and ammunition
in cm at. which 6 consecutive firings of the Ist are also developed or manufd in Belgium
& 2nd. cartridge cause detonation of the 3rd car- In the field of civilian expls and blasting ac-
tridge is detd in this test cessories, the various plants or companies manufg
Essai C. Aptitude Z l’explosio?a apr~s sejour clans these items joined together for marketing ands erv-
me atrnospb&e bwnide (Aptitude to explosion ice to customers in Belgium in an ‘Association
after remaining in a humid atmosphere). The pre- des Fabricants Beiges d’Explosifa”(AFBE). This
vbs test B is ‘repeated with cartridges that have Assocn, together with the ‘Centre de Recherches
been previously weighed and left for several days Scientifiques et Techniques pour l’Industrie des

1
 B 29

Produits Explosifs”(CRIPE) publishes every three Dynamites and Explosives cent ai”ning no NG
months, the journal ‘Explosifs” dealing with (used mainly in quarries) b)Cooppalite TA, Coop.
scientific and technical subjects related to expfs pa[ite Rouge and Cooppalite N(SA CooppaI)
The Belgian Companies affiliated with the C( Fractorite and Trr”amite 27(SAPRB) d)Nitratol
Association and now (summer 1961) remaining and Ruptol(SA d’Arendonck) e) Sabulit e B rz-sante
the sole manufactures of civilian expls
and ac- (SA La Sabulite) and f) Alsilit q(SAFNPCE at
cessories are: Boncelles)
1) SA d’Arendonck, with offices in Li2ge and plant Note: Dynamites I & 111$as well as the above
in Arendonck Brisant Explosives, can also be used in non-
2) SA de la Poudrerie Royale de Wetteren Cooppal gaseous coal mines. They are listed in Belgian
& Cie, with offices in Bruxelles and plants in Regulations as Type 1 Non Safety Mines Ex-
Caulille(founded in 1778 as a black powder plant) plosives
and at Wetteren C) SGP(S&urit6Grisou-Poussi&e) Explosives
3) SA Fabrique Nationale de Produits Cbinziques (Safety coal mines explosives, sheat~ed and un-
et d’ Explosz”/s 2 Boncelles (SAFNPCE), with of- sheathed): a) Type 11 of Belgian Regdations are
fices and a plant in Boncelles the following sheathed brisant explosives(”Ex-
4) SA de la Poudrerie d’Ornbret J. P. G erard G Cie, plosifs brisant gain~s”): Fractorite CA (contains
with offices in Li>ge and a plant in Ombret ca 10% NG) (SAPRB} Ruptol B(Contains ca 10%
5) SA Poudreries RZunies de B elgique(SAPRB), NG(Arendonck) and .$abulite 003(contains ca 14%
with offices in Bruxelles and plants in Matagne- TNT and no NG(SabuIite Plant) b)Type III o{
la-Grande, Balen, Clermont-sous-Huy and Engis Belgian Regulations are the following sheathed
6) SA La Sabulite, with offices and a plant in safety expls: Alkaiite(ca 12.5% TNT and no NG
Moustier-sur-Sambre (Boncelles); Nitro Coppalite V(ca 10% NG)(Coop-
The companies ‘Poudrerie de CarneHe”, ‘Ex. pal); Flammivore(ca 10% NG) (Arendonck); iVitro-
plosifs d’Havr6” and ‘Explosifs Yonckites* still boncellite(ca 10% NG)(Boncelles); Sabulite BV
exist in name onIy; their activities have been (ca 14% TNT but no NG) (Sabulite); Matagnite
taken over by the SA Poudreries R6unies de Bel- VIII(ca 10% NG)(SAPRB); S6curite B(ca 35% NG)
gique(SAPRB). The SAPRB is also connected (SAPRB) and Arendonck) c)Type J]] oj Belgian
with the ‘SA Afridex” (making civilian mining Regulations includes the following high safety
expls in Katanga), ‘Companhia de P61voras e unsheathed expls: Bicarbite(ca 15% NG) (SAPRB
Muni~oes de Barcarena” (Portugal) “ExPIosivos and Arendonck); An”onite (Arendonck); Nitro-
EXSA”, PerC cooppalite Vlll(Cooppal) and Cbarbrit e 418(SAPRB)
Among Belgian expls manufacturers, only Note: The last three expls contain 10% NG and
SAPRB and the ‘Poudrerie Royale de Wetteren NHaCl+NaN03 instead of the customary
Cooppal et Cie” are exporting throughout the NH4N03+NaC1. These ‘exchanged ions” type
world expls such as B1 asting Gelatin, Special safety and an excellent explosive yield
Gelatins, Ammoniagelatins, Gelignites, Semi- D) Black Powder is manufd in small quantity for
gelatins, NG Dynamites, Ammonia Dynamites, use in quarrying(Cooppal & Ombret)
Black Powder, fuses, etc. The SAPRB is the E) Ammonium Nitrate Sensitized with Oil is
sole Belgian manufacturer of plain and electric manufd for some quarrying operations (Ombret)
(instantaneous, long delay and short delay) blast- The BeIgian expls Iisted in this section are
ing caps, which are used not only in Belgium but those currently in use. There were, however, in
in other countries as well the past many expl compositions either originat-
The current Belgian Industrial Explosives are ing in Belgian or in use there. As the purpose of
classified as follows: this book is to describe all kinds of expls, they
A)eGelatinous” Explosives: a)Dynamite Type will be included elsewhere in alphabetical order
I [kind of ammoniageIatin of 80-85% ,RWS (relative ‘The following Belgium Expls are expected to
weight strength)] (manufd by SAPRB ~d by SA be described separately: Alkalite, Alsilite, Ama-
Cooppal) b)Dynamite Type III (kind of ammonia- site, Ammoncarbonite, Antigel de Sfiret@, Anti-
gelatin, 70% RWS) (SAF?RB and SA Cooppal) and $SOU Exp[osi/s, Antigrisous F avieriGrisoutines),
c)Blasting Gelatin, cotitg 93% NG(SAPRB and Asphaline, Baelenite, Cannel Powder, Casteau
SA CooppSI). All these expls are very brisant (Explosifs de), Centrality Ril, Centrality TA,
Clerrnonite, Colinite-arztigr is o uteuse B, Cooppal-
B) ’*Brisant” Explosiues(non-gelatinous): a)NG
ite, Cooppal Poudre n02, Delatt re(Explos ifs dej,
 1

B 30

Divine(Explosi /s de), Di&ite, D ynarni t e 111, 11 )Fuzes (same as above)

Dynamite Z 1‘ammoniaque de Matagne-Iu-Grande, 12) Grenades, SAPRB manufd hand & rifle grenades
Dynamite- antigel de la Dyn a rnetn”e #Arendonck, of the following types: fragmentation, tear &
Dynamite-antigrisouteuse I V(Dynamite de S~ret&), smoke; while UMAL, ME CAR &’ FN m anufd AP
Dynamite-anti gri souteuse V(Dynarnite de B aeien rifle grenades with shaped charges
Wetze[), Dynamite- gomme A, Dynamite-gomm e de 13 )Guns - see under Belgian Weapons
Matagne-la-Grande, Favied Explosifs de), FIam - 14)Lead Azide (LA) and Lead Styphnate (LSt)
mivores, Forcit es, Fortis( POU dres # Heusscben) (Matagne plant of SAPRB and Zutendael plant of
Fractorites, ~’ulmicoton cb10rat5 (Poudre), G;la- FN)
tine a 1’ ammoniaque A ou no 3, Gdat i ne -carbon- 15) Machine Guns, Machine Pistols and Submach-
ite, G61atine-dynamites, G61at in e~ explosibles, ine Guns- see under Belgian Weapons
GZlatine explosive de guerre, GZ[ignit e 21’ am - 16) Mercury Fulminate (MF)(same as Lead azide
moniaque, G~lignit e d’Arendonck, Gn”sounite s plants)
(same as Antigr isous Favier), Grisout i n es, 17) Mines, such as undetectable antitank mines
Grisoutites, Koblencarbonite, L ~(Poudr e) de ATK-1, ATK-111 & ATK IV with antilifting devices
Cooppal, Macarite, Matagnit es, MZgadyne, M~la- and undetectable antipersonnel mines AP 35M5Bg
nite, Min&ite, Minite d’Arendonck, Minolites, are manufd by SAPRB
Mii Ilerite, N;oclastite, Nitrobaelinite 3, Nitro- 18) Mortars - see under Belgian Weapons
cooppalite, Nitroferrite, O xo n i te, P ermite, Per- 19) Nitric Acid(Acide azotique) by the Comptoir
monite SG P, Potentite ou Tonite, Poudre amide Beige de l’Azote(COBELAZ)- 5 plants; main
(de Gaens), Poudre blancbe Cornil, Poudre de office at Bruxelles
Bois de Wetteren, Poudre Coo ppaI(de cb as se), 20) NitroceUulose (Caulille plant of SA Cooppal)
Poudre Cooppal (de gueme), Poudre Curtis et (Limbourg)
Andr@, Poudre GaZ ns, Po u dre Vr il, P ou dres de 21) Nitroglycerin (Caulille plant of SA Cooppsl;
Wetteren, Pudroli@e, Pyrol ithes( P yrolytbes), Balen plant of SAPRB and Arendonck plant of
Pyronomes, Sabuli tes, Saxifragine, S;cu rites, SA d’Arendonck)
Sengitbe, Stubenraucb(Explos i fs de von), Super- 22)Pisto/s - see under Belgian Weapons
forc ite, Tonite(same as Pot entite ),fii t ori t es, 23)Primers (Amorces) (Zutendael plant of FN and
V~lten’ne, Wallonites, W61terine, W e tteren(Poudre Matagne plant of SAPRB)
de guerre de), Xantbine(Pou d re de) and Yonck- 24) Propellants, Smokeless (Poudres saris fum6e ).
ites Clermone plant of SAPRB and Caulille plant of
T~e f oIl owi ng list inc Iudes Belgian Ex- SA Cooppal manuf both single- and double-base
plosives, Propellants, Ammunition and Related proplnts which are mostly of the same types as
Items used mostly for military purposes : currently used in the US. In time prior to wars,
I)Black powder (Pou d re no ire)- for fuses and mostly French types(such as Poudre B & Bal-
military purpos es(Clerm ont plant o f SA PRB and Iistite) as well as British types(such as Cordite)
Wetteren plant of SA Cooppal) were used in Belgium. Clermont plant also manuf
2) Carbines - see under Belgian Weapons Ball PowdefiPoudre sph6rique) while Composite
i) Cartridges(Cartouches) - for s m all arms(FN at propellants are manufd at the Balen plant of
Herstal ); for arti 11er y(FN at Herstal, Forges de SAPRB ,
Zeebrugge and Met allurgia) 25)F!evolvers- see under Belgian Weapons
4)Cyclotetrametbylenetetran i tra mine(HMX) 26)R ifle Grenades- see Grenades
(probably at the Bal en plan t of SA PRB) 27)Rifles- see under Belgian Weapons
5)Cyclotrim etbylenetrinitrami n e (Hex og$ne) 28)Sulfuric Acid(Acide s~fmique) and Oleum
(RD X ) ( Brden plant of S AP RJ3) (O16um)- by the Syndicat Beige de l’Acide ‘SuI-
6)Delay and Relay Elements for Fuzes and Blast- furique- 16 plants; main office at Bruxelles
ing Equipment (Matagne-Ia-Grande plant of SAPRB) 29)Tetracene(Matagne plant of SAPRB and
7)Detonating Cord(Cordeau d6tonant ) (Matagne Zutendael plant FN)
plant of SAPRB) 30]Tracers (Traceuts) (Zutendael plant of FN and
8)D etonators and Blasting Caps for military and Matagne plant of SAPRB)
civilian uses(Matagne plant of SAPRB) Note: The SA des Ezplosifs d’Havr6, now absorb-
9)Dinitroto2uene (Balen plant of SAPRB) ed by SAPRB, also seems to be a manufacturer
10)Fuses (Wetteren pI ant of SA Cooppal and of tracers
Engis plant of SAPRB) 31) Trirzitrotoluene( TrotyI) (Balen pIant of SAPRB)
 B 31

32) Weczpons- see the list below Mons)(gallery for testing expls and accessories
The following list includes Belgian Plants intended for use in gaseous or dusty coal mines)
Currently Manufacturing Ammunition, Weapons The following list includes the principal Be/.
and Related Items: gian weapons manufd in the past and at present
A)FN(Fabrique Nationale) dArmes de Guerre in by FN at Herstal and by some other plants:
Herstal(Li5ge), founded in 1889, one of b world’s 1) Revolvers and Pistols, Nagant Revolver cal
largest [various weapons such as revolvers, rifles 9mm(.354), was adopted in 1878 for officers and
(including the FN rifle adopted for NATO troops), a slightly modified model was adopted in 1883
machine guns & pistols, guns and mortars; various for non-commissioned officers
grenades, cartridges, jet engines, trucks, etc(see Note: Nagsnt revolvers, CSI 7.5 & 7.62mm, have
the list of Belgian ammo and weapons given below).] been used in Russia for about 70 years
There is also a pIant at Zutendael, which rnanuf These revolvers were superseded in Belgium
LA, LSt, Tetracene, primers and tracers by the FN Browning Automatic Pistol, Mod 1910,
B)SA Beige de Mecbanigue et d’Armemeti (MECAR) cal 7.62mm(.S2”), magazine capacity 7 rounds.
at P etit-Roeulx [various shaped charge ammuni- This pistol was in turn superseded ca 1935 by
tion and weapons, including the Energa rocket the FN Browning High Power Pistol, cal 9mm,
grenade, the 90mm A/T gun, called CATI, and 13 rounds, which is still in use. FN is also
the A/T weapon called Blindicide(qv)] manufg a 6.35mm and a 7.65mm automatic pistol
C) SAPRB (SA des Poudreries R6unies de Bel- Note: Many other automatic pistols, ranging in
gique) at the Balen plant(loading and assem- caliber from .25” to .38”, have been manufd by
bling of various kinds of ammunition, such as FN, most of them for ezport. The same may be
artillery, mortars, grenades, mines, rockets, etch said of other pistols formerly msnufd in Belgium
at the Matagne-1 a-Grande pl ant(various fuzes, at smaller plants, such as the Bayard, Clement$
primers and tracers) Pieper, etc. AH these plants were absorbed by
Note: The 5A de Explosifs d’Havr6 plant, manufg the FN
tracers etc, is now absorbed by SAPRB 2) Ri/les(Non-Automatic). Albini-Broendlin, cal
A gallery for testing coal-mining expls is loca- 60”, single-shot rifle, was the first Belg breech-
at Balen loader. It was used since 1867. T%e next singie-
D) Forges de Zeebrugge at L i~ge (metal parts for -shot rifles were Gras Mod 1874, cal 1 lmm and
artillery & mortar ammunition and for rockets) Comblain Mod 1881, cal 11.6mm. The iatter rifle
E) UMAL(Usines et M6tsllurgie d’Aluminium et was used by the Belg Civil Guards as late ae
d’Alliages L6gers) at Burcht (near Antwerpen) WWII. . These rifles were replaced by the Mauser,
(manuf same items as MECAR) Mod 1889, cal 7.65mm, magazine capaciv 5
F) Metullurgia(Malines), subsidiary of SAPRB rounds, rifle and carbine. They fired round-no sed
(metal parts for artillery ammo, including steel bullets.
cartridges cases, especially perforated ones) After WW I, the Mauser rifles, Gewehr ’98,
The following list includes Belgian official cal 7.92mm, taken from the Germams, were con-
laboratories and facilities for testing explosives, verted in Belgium to the cal 7.65mm rifle.
ammunition and Weapons(excluding control lab- These were known as the Mauser Mod 1935.
oratories} A similar rifle, known as Mauser Mod 1936,
a) Arsenal de Munitions at Zwyndrecht (near was obt by modifying the Belg Mauser Mod
Antwerpen) (Inspection labs for military expls, 1889, Both of these models fired pointed bullets
propellants and ammo) and some were used as late as WWI1
b) Belgian Army Proving Grounds at Brasschaet In addn to Mauser rifles, such as cal 7.9mm,
(near Antwerpen) and at E Isenbom(nea the Ger there were also some reworked 13rit & US rifles
man border) of WW1, such as cal .303” Lee-Enfield rifle
c) CRIPE (Centre de Recherches Scientifiques et Not e: “While the regular Belgian Army .1s now
Techniques pour l’Industrie des Produits Ex- equipped with automatic rifles (see below), the
plosifs) in Sterrebeek(ne= Bruxelles) (Testing non-automatic rifles, system Mauser and Lee-En-
of industrial expls) field, are still in use by the 13e~g Gendsrme~le,
d) lBHP (Institut Beige des Hautes Pressions), Police and Customs
Tir National, Bruxelles 3) Rifles, Automatic (Light Machine Guns).
e) Jnstitut National des Mines in Paturages (near Chauchat Machine Rifle, cal 7.65mm, known as
 B 32

Mod 15 (Fusil Mitrailleur CSR6), fired round-nosed after WWII ; 57mm A/T Gun(semi-automatic fire);
bullets and had magazine capacity of 15 rounds. 57mm Bofors Gun; 75mm Field Guns; 76mm Guns;
It was used during WWI and later replaced by the 90mm A/T Gun, Mod l(called CATI); 105mm Gun;
FN Browning Rifle Mod 30, cal 7.65mm, mag 105mm Howitzer; 120mm Gun, M31; and 8-inch
capacity 20 rounds, which fired pointed bullets Gun
More recent types of BeIg automatic rifles 8) Mortars: 2-inch Mortar; 60mm Mortar(US);
include: FN Browning Automatic rifle, cd 30”; 3-inch Mortar; 81mm Mortar(US); 4.2-inch Mortar
Bren Gun, cal .303” and FN Light Automatic (US M2> add 4.2-inch Mortar(British Heavy)
Rifle, C(rd 7.62mm, magazine capacity 20 rnds; Note: During WWI, a Belg officer Van Deuren
this rifle, designated as FAL is now used by invented a mortar which was used during VWII
~elgian and NATO troops. There is also the FN but was discarded afterward
Self-Loading Rifle, cal .30”, magazine capacity 9)Rocket Launchers. 83mm Blindicide for firing
10 rounds. it is designated as AFN cal 30- the Energa rocket, called ROCK-HEAT 83mm
4) Machine Guns(Light & Medium) and Machine Note: Energa rockets are described in conf
Pistols. Mitrailleuse(multibarrel), designed in PATR(Picatimy ArsenaI Technical Report) 2097
1851 by Capt Fafschamps of the Belgian Army (1954) and in PAMR’s(PicArsnMemorandum Repts)
and improved by Montigny, a B elg engineer, was 80(1955), 86(1955) and 86(Supplement)( 1956)
never used by the Belgians but was adopted 10) Grerzade Launchers. Grenade Launcher DB T,
by the French in 1867. Berthier-Pasha MG, in- invented in Belgium betw WWI and WWII, con-
vented in 1908 by the French officer A. Berthier, sisted essentially of a Mauser breech mechan-
was produced in small numbers for the US Govt ism on which was screwed the launching cup
during wwI by the now extinct Belgian firm of
Bellenite. An ezpl based on nitrolignin and
Pieper in Herstal
manufd in. Sydney, Australia at the beginning of
The first MG used by the Belg Army was the
this century
Maxim 08, cal 7.6Smm, water-cooled. This gun
Refi Daniel(1902), 58
was used from before WW1 until WWII. During
WWI the Belgians also used some Colt MG, Mod
Bellford Powder, patented in 1853 in England,
1895, caI 7.65mm, firing round-nosed b~lets.
was prepd by impregnating the grains of black
This gun was designed by John Browning, an
powder with a satd soln of K chlorate and then
American. A later model fired pointed bullets.
drying for 4 days at 100°F
Modification of Maxim 08/15 (wate~coo1ed) and
Refs: l)CundiH(1889) in L@ 5,292(1892)
Maxim 08/18( air-cooled), both cal 7.65mm and
2)Daniel(1902),59
obtd from the Germans after wI, were used by
the Belgians during WWII and then discarded
Bellites are expls consisting of AN and mono-
The more recent weapons include: FN MAG
or di-nitrobenzene s(MNB and DNB). Many mod-
Machine Gun, CSI 7.62mm NATO, belt fed(steel);
ifications exist and some compns contain K ni-
FN Machine Pistol, caI 9mm Parabellum, mag-
trate instead of AN. The original BeUite: AN
azine capacity 25 or 32 rounds; Browning MG, caI
34.5 & MNB 65.5%, was proposed ca 1885 by
.50”, belt fed(Mitrailleuse .50-A-Avi), correspond-
C.Lamm of Sweden and was manufd at Rotebro,
ing to the US Browning .50WM2
near Stockholm. Bellites were patented in 1885
5) Sub-Machine Guns. Sten Gun. cal 9mm, mag-
in England and manufd by the Lancashire Ex-
azine capacity 28 rounds; Vigneron Gun, cal gmm,
plosives Co,Ltd. Marshall(Refs 4 & 5) gives
mag capacity 32(not manufd by FN) and Thompson
compns of the following British “permitted”
Gun, cal 45”, mag capacity 32. FN is now manufg
Bellites:
for Belg Army the 9mm P arabellum type sub-ma-
chine, Designated UZ? ------ --s-—- ------ ______ ______ _.

Note: Schmeisser-Bergmann sub-machine gun, cal . Bellites . AN . DNB . NaCl .

9mm, adopted in the thirties, was manfd by Pieper No 1 83.5 16.5 -
Co; discarded after W11 No 2 93.5 6.5 -
6)Machirze Guns, Heavy. 20mm Oerlikon and No 3 61 12 27
Hispano-Suiza MG’s No 4 66 14 20
7) Guns(Cannons) and Howitzers: 40mm Bofors Nola 68 12 20
-- —--- ------- ______ ______ ______
L60 Gun; 47mm Single-shot A/T Gun(discarded
 B 33

The No 1 & No 2 compns are also listed by Benedite. An AN expl permitted in England since
Cook(Ref 9). They passed the Woolwich Test. 1898: AN 93-95 & rosin 7-5 (Ref, p 61). It was
The No 3 & No 4 compns passed the Rotherham identical with the Ger expl Westfalit Nr 1, de-
Test, whereas the No la passed the Buxton scribed in Ref,p 804
Test Refi Daniel(1902), 61 & 804
.Kostevitch(Ref 4a) gives for a Rus Bellite
used during WW1 in bombs and grenades: AN83 Beneke Explosives, patented in England in 1896,
& DNB 17%. A Rus Bellite(BeIit) listed in Ref 8 were prepd by melting rosin and mixing it with
consisted of AN 80, DNB 8 & TNX 12% 1-1.5 parts of finely pulverized K bichromate and
The so-called Black Eiellite consisted of AN 1-1.5 ps Na carbonate or bicarbonate. ,After
61, TNT 12, NaCI 24 & native graphite(plumbago) cooling, the mass was pulveri zeal, mixed with
3% (Ref 6a) additional 4-5 ps of rosin and 93-94 ps of AN and
Bellites were rnanufd by heating the well*mixed reheated to coat the AN trysts with rosin. These
ingredients to above the mp of the nitrocompd to e xpls were relatively non-hydroscopic. Other
completely coat the AN(or K nitrate) cfysts with Benek6 expls consisted of Iiq hydrocarbons
nitrocompd in order to render them non-hygr- mixed with K bichromate(or chlorate, or permangan-
scopic. The mixt was pressed into cartridges ate) and finely pulverized charcoal. An expl pat-
while still hot ented in 1900 consisted of AN and some K chlor-
Refs: l)cundill( 1889) in MP 5,292(1892) ate
2)Daniel(1902), 59-60 3)Gody(1907), 596 Refi Daniel( 1902), 62-3
4)Marshall 1(1917), 38~90 4a)M.M.Kostevitch,
‘Burning Ground”, Imp d’Art Voltaire, Paris Benet-Mercie Automaticwas developed in
Rifle
(1927),40 5)MarshaIl 3(1932), 119 6)Thorpe 1908 and adopted in 1909 by the US Army. It
4(1940), 465 & 554 6a)CondChemDict( 1942)/288 was the forerunner of the Browning automatic
(not found in later editions) 7)Bebie(1943), 32 rifIe, used since 1917
8)Shilling(1946), 97-8 9)Cook(1958), 10 Re# J. J. O’Conner,Ordn 37,271(1952)

Bellot, Nicolas( 1792-1882). A Ger expls c~mist Bengal Fire Powder. A mist used during WWl
who may be considered as a designer of the for signaling purposes: Ba nitrate 67, Amm
modern percussion cap. He founded in 1829 the picrate 25 & sulfur 8%. It burned with an intense
firm of Sellier & Bellot, which Iater was renamed green flame. By substituting Sr nitrate for Ba
Zfidhtitchen- und Patronenfabrik nitrate a red flame was produced
Refi Anon, SS 24, 271(1929) RefiColver(1918),341

Bengaline was a powder contg K chlorate 40 &

Bell Powder, patented in England in 1898, con-
bran 60%, proposed in 1882 by Medail
tained K nitrate 70.2, pulverized coal 18 & sulfur
Re/:Daniel(1902 ),63
11.8%
Refi Daniel< 1902)* 58
Benite. See under Black Powders Containing
Bender Explosive.An older Fr expl, known also Potassium Nitrate
as Grisoutine Comprim6e
Bennet Powder, patented in 1861 in England,
RefiDaniel( 1902), 363
was a black powder in which 7% of lime was
Benedict Explosives intended to
were compns
incorporated
replace MF in primers and detonators. The R efi Daniel(1902),63
foUowing compns are described in the literature:
Simple: K chIorate 38.70, P(amorphous) 19.35,
minium(Pb~04) 38.70 & rosin 3 ~25%; Double: K Bent & Talley Explosives, patented in 1909(USP
chlorate 79.18, P(amorphous) 8.33, Sb trisulfide 943589), included several formulations, among
8.33, S(subIimed) 2.08 & K nitrate 2.08%. “Minium them: AN 50-80, NG 2-10P Mn dioxide 7-20, com-
could be replaced ‘by HgO or Mn dioxide minuted Zn(ablue powder”) 7.2-23.5 & Zn oxide
Refs: l)CundiIl( 1889) in MP 5,292(1892) 2)Da- 0.8-2.5%. They might also contain starch, char-
niel( 1902),60-1 3)P4rez Ara( 1945), 207 coal, MNN, PA, etc
 t

B 34

Bent Barrel Gun or Around the Corner Gun is diatomaceous earth), the presence of gritty
described as Krummerlauf in PATR 251O(PB particIes has limited its use from a safety stand-
161270)( 1958),p Ger 103. It must be noted that point
a similar bent barrel was patented during WWI US military requirements for 13entonite are
by J. Wister, USP 1187218(1918) but it was in- covered by Specifications MIL-B-12208A(CE )
ferior to the Ger device and MIL-B-10456A(CmlC)
Refi P .P.Sharpe, “The Rifle in America”, Funk Re/s: I)Thorpe 1 (1937 ),663-4 2)USBurMines
& Wagnalls,NY(1947),38-40 TechPaper 609, “Bentonite; Its Properties,
Bentonite or Activated Cloy. A broad term ap- Mining, Preparation and Utilization”(1940)
plied to material which has been derived from 3)Aerojet Engineering Corp Rept No 192(1946),
volcanic ash in which the mineral Montmorillonite 17 4)Kirk & Othmer 1( 1947),229( under Absorp-
predominates. Bentonite was first recognized in tion) and 4(1949), 28 & 53 (under Clays) 5)M.w.
1898 in Fort Benton(Wyoming) shales and has Swaney, USP 2521424 (1950) & CA 44, 11010
since been found in thick-bedded deposits over (1950)
a wide area in Western US(Ref 1)
According to Kirk & Othmer(Ref 4), these clayq Benton’s Electro.BalIistic An in-
Pendulum.
when activated by an acid treatment, consist of strument used in Springfield Armory and Frank-
52% Si02, 14% A1203, 4% MgO, 2.5% Fe203 and ford Arsenal in the 1870’s for detn of velocities
small quantities of other oxides of projectiles. A modified model was known as
Bentonites may generally be divided into two Thread Velocimeter
classes: a) Those capable of absorbing large Refi J .G.Benton, “Description of Thread Veloci-
smts of water and which swell tremendously in meter”, Springfield National Armory, Springfield,
the process. They also have the property of re- hiass(1873)
maining in suspensions in thin water dispersions
and b) Those that absorb no more water than Benzalaminaguanidi.l,6.dinitro.2-(aminoguanil)
ordinary plastic clays or Fuller’s earth and do l biguanidine benzalhydrazone. See Vol l,p A215-L
not swell appreciable y. They settle rapidly in thin
water dispersions Benzolaminophenol. See Benzylideneaminophenol
The raw Bentonite consists of about 10% psr-
ticles larger then 10P and about 70% smaller l.BenzaIomino.5.phenyla(orIH).tetrazole or
than 0.51.t. One gram has a total surface area of l.Benzylindene.amino.5.phenyla(or1H).tetrozole,
ca 50000cm2. A high-grade Bentonite will ab- C6H5.$-N(N:CH.C6 H5)-~, mw 249.27, N 28.10%;
sorb nearly 5 times its wt of w and will increase N .—-— . ..— N
in VO1 up to 15 times its dv bulk. The swelling ndls(from ale), mp 105°; expl mildly on rapid
process is reversible if less than 10% of alkali heating above mp; mod sol in eth or ale; diffc
is present. With 6-7 parts of w Bentonite forms sol in hot w. Can be prepd by heating on a steam
a gelatinous paste and with 20ps of w it forms bath benzazide-benzalhydrazone in alc or bv
a thin sol which is stable for months. When 2ps heating benzylidene-[~ chlorobenzylidene] -hydra-
of wet Bentonite are blended with lp of wet Cu zinc with NaN3 in alc(Refs 1,2 & 3)
acetylide, the mixt can be air-dried w/o expln Refs: l)Beil 26,(113) & [216] 2)R.Stoll~ &
and used as a fungicide(Ref 5) F. HeHwerth,Ber 47,1139(1914) 3)R.Stoll~ &
13entonites have been used for clarifying and A. Netz,Ber 55,1300(1922) 4)R.Stoll~ et al,
bleaching oils, for emulsifying asphalts & other J. PraktChem 138,3(1933) & CA 27,4798(1933)
water immiscible, as a suspending, thickening
oL. paste-forming agent and for other purposes. %Benzal aminw2~phenyl@ (or 2H)~tetrazole or
It has been suggested as an emulsifier in some SBenzyl iden~omin~2~phenyl@ (or 2H)=tetrazole,
expl compns and as an absorbent of some liq C~H~.CH:N.$=N—~ .C6H~, mw 249.27, N28. 10%;
expls(see Note). Some of the Aerojet Engineering N-N
Corp proplnts contain Bentonite. Eg: RL-206 ndls(from ale), mp 123° (with browning); mod sol
Propellant consists of Paraplex Ap-31 27.35, in eth; sol in ale; insol in w. Can be prepd by
styrene 27.35, Bentonite 44.76 & t-butyl hydrogen heating on a steam bath 2-phenyl-5-aminotetia-
peroxide 0.54%(Ref 3) zole with an excess of benzaldehyde(Refs 1 & 2)
Note: Although Bentonite is a good absorbent Re/s: l)Beil 26, [344] 2)R.Stol16 & O. Orth,Ber
for liq expls(it absorbs twice as much NG as 58,2104(1925)
 B 35

Benzalaniline. See Bermylideneaniline 2,4,6. Trinitrobenzaldehyde (TNBA),(02N)3C6H2 .C HO;

mw 241.12, N 17.43%, OB to C02 -56.4%; COI platea
Benzalazine. Same as Banzaldehyde Azine (from benz), mp 119°, Q: 732 cal/mol or 3035cal/g
(Ref 3); sol in w or benz. Can be prepd by severaI
BENZALDEHYDE AND DERIVATIVES methods(Refs 1 & 2). One of the best methods of
Benzaldehyde (Pbenylaldebyde; Benzene Carbon- prepn is the acid hydrolysis of the condensation
al or Artificial Almond Oil) (called 1‘-Oxo-l-methyl product of TNT with p-nitroso-dimethylaniline:
-benzol; Benzaldehyd or Bittermande161 in Ger), (02 N)3C6H2CH:N.C6H4 .N(CH~)2+H2~
CGH5 .CHO; mw 106.12, CO1 Iiq, mp -26° (resolid- (02N)3C6H2 .cHO+H2N.C6H4 .N(CHa )2. The by
ifies at -560), bp 179°, d 1.046 at 20°; sol in alc -product is p-am inodimethylaniline
or eth; SI sol inw; vap press data in Ref 4. Its Trinitrobenzaldehyde is a HE about as powerful
toxicity and hazards are described by Sax(Ref 5). as TNT, but less powerful than PA. It is S1 more
Benzaldehyde is produced commercially by the brisant than TNT(ca 117%) as detd by the Sand
catalytic oxidn of toluene(Refs 2 & 3> other Test(Refs 4 & 5)., The min chges of MF or LA
methods of prepn are given in BeiI(Ref 1). Its reqd for its deton are about 50% of those reqd for
uinitroderiv is expl TNT. Present manufg costs prohibit the use of
Re/s: l)Beil 7,174(113) & [145] 2)L.D.Margolis, TNBA as a coml or military expl. TNBA forms
ZhPriklKhim 14,827-3 1(1941) 3)Kirk & Othmer many condensation products with org compds,
2(1948),416 4)Jordan(1954),92 & 106 5)%x(1957), some of which are expls(Ref 2)
342 Re/s: l)Beil 7,265 & [207] 2)A.Lowy & !5.H.
Azidobenzaldehyde, N3 .CGH4 .CHO, mw 147,13, N Batz,JACS ~,343(1921) 3)W.H.Rinkenbach, JACS
28.56%. The o-(or 2)-azido deriv, plates, mp 37.5°, 52,116(1930) 4)L.V.Clark,IEC 25,1387(1933)
is listed in Beil 7,266 & (145) 5)Blatt,0SRD 2014(1944)
Azobenzaldehyde. See VOI l,p A646-R Other Derivatives of Benzaldehyde
Azoxybenzaldehyde and Derivatives. See VO1 1, Benzaldehyde.3.diazoniumchloride,
p A666-L 0HC.C6H4 .N(~N)C1 . Its stannic chloride salt,
Nitrosobenzaldeby de. The o(or 2)-, m(or 3)- and [20HC.C6H4.N(~N)Cl + SnC14], CO1 ndb, mp expl
p(or 4)- derivs are described in Beil 7,242 & (136) mildly on heating in a flame; was prepd from 3-nitro-
Nitro Derivatives of Benzaldehyde benzaldehyde, stannous chloride in coned HC1 and
Monanitrobenzaldehyde, 0ZN.C6H4.CHO; mw Na nitrite, as described in Refs 1 & 2
151.12, N 9.27%, OB to C02 -143%. Three isomers Refs: I)BeiI 16,538 2)F. Tiemsnn & R. Ludwig,
are described in Beil: O(OT 2)-Nitrobenzaideby de, Ber !5,2045(1882)
yel ndls, mp 43.5-46°, bp 153°; v SI SO1 in aIc 2.6.Dinitrobenzaldehyde.4.diazoniumchloride,
or ech. Prepn and other props in Ref 1; m(or 3) 0HC.C6HZ(N02)2. N(;N).CI; mw 258.58, N 21.67%;
-Nitrobenzaldebyde, yel ndls, mp 57.5-59°, bp lt yel ppt; mp expl on heating without melting;
164°; sol in ale, eth or chlf; so sol in w. Prepn readily sol in w; insol in common org SOIVS. Can
and other props in Ref 2; P(OT 4)-Nitrobenzalde- be prepd from 2, 6-dinitro-4-amino-benzaldehyde-
hyde, yel prisms, mp 104.3-106-5°; Q: 793 cal/mol oxime in abs alc and HC1 by reaction with amyl
or 5251 cal/g(Ref 4). Prepn and other props in nitrite. Other props are given in Refs 1 & 2
Reefs 3 & 5 Re/s: l)Beil 16,538 2)F.Sachs & H. Kantorowicz,
Re/s: l)Beil 7,243,(136) & [185] 2)Beil 7,250, Ber 39,2762(1906)
(139) & [190] 3)Beil 7,256,(141)& [1961 4)W.H.
Rin kenbach,JACS 52, 116(1930) 5)W.Davey & Benzaldehydeazine and Derivatives
J. R. GwiIt,JCS 1950,204-8 Benzaldehydeazine; B enzalazine; B enzylidene-
Dinitrobertzaldeyhde, (02N)2CG~CHO; mw 196.12, azine; or Dibenzalbydrazine (called Dibenzal-
N 14.29%; OB to C02 -89.2%. Two isomers are hydrazin; Benzaldazin; sym-Diphenylazimethylen;
described in Beil: 2,4-Dinitrobeazaldebyde, yel and Dibenzylidenhydrazin in Ger),
prisms, mp 72°; bp 190-210° at 10mm; sol in benz; C6H5.CH:N.N:CH. CGH5; mw 208.25, N 13.45%, is
insol in ale, eth or W. Prepn and other props in described in Beil 7,225,(123)& [171]
Refs 1 & 3.2, 6-Dirzitroberzzaldehyde, yel Ifts N.[(a.Azidobenzylidene).N’.benzylidene].azine
(from dil AcOH), mp 123 0. Prepn and other props (called Benzazidbenzalhydrazon in Ger),
in Ref 2 C6H5C(Na):N.N:CH. C6H~; mw 249.27, N 28:10%;
Re/s: l)Beil 7,264 & [205] 2)Beil 7,(144) & yel ndls(from eth or ale); mp 72°, expl at higher
[206] 3)OrgSynthCo11 VO1 2(1943),233 temp on rapid heating; sol in eth or ale; insol in W.
 I

B 36

It was first prepd in 1914 by Stol16&Helwerth Azidobenzaldehydeoxime, N3 .C6 Ha .CH:N.OHj mw

(Ref 2) by treating benzalbenzenylhy drazone- 162.15, N 34.56%. Two isomers are described in
hydrazide with nitrous acid. A more convenient the literature: 2-Azidobenzaldeby deoxime, CO1ndls
method(Refs 3 & 4) is to heat for about 1 hr, under (from benz), mp 103-103.5°; readily SO1 in hot benz
a reflux condenser, an alc soln of benzalbenz- or hot Iigroin; can be prepd in several ways(Refs
hydrazidechloride, C6H5.C(Cl):N.N: CH.C~H5, and 1 & 3) and 4-Azidobenzaldeby deozime as a- and ~-
then to cool the resulting mixt to ppt the trysts forms. The a-form exists as tablets(from dil ale),
This compd is a mild expl but it may serve as a mp 98°, readily sol in petr eth or in most other
starting material for the prepn of the”derivs of SOIVS. The (3-form exists as yel ndls(from benz),
l-aminotetrazole, namely l-amino-5 -phenyltetrazole mp 142° (dec), readily sol in most common Org
Refs: l)Beil 9,(136) 2)R.Stoll< & F. HeIwerth,Ber SOIVS except benz or petr eth. Its methyl ether is
47,1139(1914) 3)R.StoIle & A.Netz,Ber 55,1297 described in Ref 1. The prepn and other props of
(1922) 4)R.Stoll; et al, JPraktChem 138,3(1933) both the a- and ~-forms are described in Refs 2&4
Mononitroberzzaldeby deazine, C ,4 HIIN302, mw Re/s: l)Beil 7,266 2)Beil 7,266 & (145)
253.25, N 16.59%. Three isomers are described in 3)E.Bamberger & E. Demuth,Ber 34,1336(1901)
Beil 7,249,255,261 & (140) 4)M.O.Forster & H. M. Judd,JCS 97,257(1910)
‘i~itrobenzazde~ydeazi~e’ c 14H1ON404 ; mw298”25> Mononitrobenzaldebydeoxirne, 02 N.C6H4 .CH:N.OH,
N 18.79%. Three isomers are described in Beil 7, mw 166.13, N 16.88%. Three isomers are described
250,255,261 & (138,140,143) in Beil 7,248,249,254,255,259, (138,139,142) &[188
4,4’.Dinitramino.3,5,3’,5'.tetrabromo.benzaldehyde 192,193,198,199]
azine, 02N.HN.C6 H2.Br2.CH:N.N:CH. BrzC6H2.NH- Dinitrobenzaldeby deoxime, (02 N)2C6H3 .CH:N.OH,
.NOZ; mw 643.93, N 13.05%; ndls(from ale), mp mw 211.13, N 19.90%. TWO isomers are described
expl on heating. Was prepd by treating 3, 5-dibromo in Beil 7,265,(144) & [206]
-4-nitramino-benzaldehyde with an aq soln of 2,4,6 Trinitrobenzaldehydeox ime,
hydrazine sulfate (02N)3C6H2.CH:N.0H; mw 256.13$ N 2L88~0
Re/s: l)Beil 16,[348] 2)L.Elion,Rec 42,160(1923) Crysts(from ale), mp 158°; ‘asilY sol in alc or
Tetranitrobenzaldehydeazine { called Bis-[dinitro acet; in sol in w. Can be prepd by treating 2 ,4,6-tri-
-benzal]-hydrazin or Tetranitro-benzaldazin in Ger), nitrobenzaldehyde with hydroxylaminehy drochloride
Cl 4H8N50~, mw 388.25, N 21.65%. Two isomers in alc soln in presence of soda. Its expl props
are described in the literature: were not investigated
2,4,2’, 4*- Tetranitrobenzaldeby deazine, Re/s: l)Beil 7,265 2)F.Sachs & q’. Everding,Ber
(02N)2C6H3.CH:N.N: CH.C6H3(NOZ)2, golden-yel 36,961(1903)
ndls(from hot MNB,) mp 246°; insol in ale. Can be 2sNitrobenzaldehYdeoximea&diazoniumchloride,
prepd by treating an alc soln of 2,4-dinitrobenzal- H0.N:CH.C6H3(N02 ). N(!N).C1; mw 228.60, N 24.51%;
dehyde with hydrazine sulfate in the presence of pink ndls, mp stable at 60-80° but expl on strong
aq Na acetate. Its expl props were not investigated heating. Can be prepd from 2-nitro-4-amino-phenyl
Re/s: l)Beil 7,265 2)F.Sachs & R. Kempf,Ber 35, acetic acid in cold coned HCI by reaction with
1233(1892) amyl nitrite. On heating with ale, this compd forms
2,6,2’, 6’-Tetrarzitrobenzaldeby deazine, 2-nitrobenzaldehyde-anti-oxime(qv)
(OzN)2.C6H~.CH:N. N: CH.C6H3(N02)2, yel ndls Refs: l)Beil 16,538 2)S.Gabriel & R. Meyer, Ber
(from acet), mp 246-7°; easily sol in MNB, sol in 14,826 & 2334, Footnote 1(1881)
glac ACOH or acet; diffc sol in ale, eth, chlf or >Nitrobenzaldehydeaxime4diazoniumchloride,
ligroin. Can be prepd as above from 2,6-dinitro- H0.N:CH.C6H3(N02 ). N(~N).Cl; mw 228.60, N 24.51%;
benzaldehyde. Its expl props were not investigated red plates or ndls, mp expl on heating. Can beprepd
Re~s: l)Beil 7,(144) 2)S.Reich & G. Gaigailiar,, by treating amyl nitrite with 3-nitro-4-amino-phenyl
Ser 46,2385(1913) acetic acid in a mixt of HCI, eth & ale. On heating
with ale, this comp forms 3-nitrobenzaldehyde-anti
Benzaldehydeoxime and Derivatives -oxime
Benzaldehydeoxz’me (called Benzaldoxim in Ger), Refs: l)Beil 16,538 2)S.Gabriel,Ber 15,837(1882)
C, H, NO, mw 121.13, N 11.56%. It exists in two ~. Benzaldehyd~xim~picrylether,
configurations a-or benz-anti-aldoxime and ~- or C6H5.CH:N.0.C6HZ(N02 )3; mw 332.23, N 16.87%;
benz-syn-aldoxime. Both forms are described in yel prism s(from acet), mp 18 l-2°(dec); prepn and
Beil 7,218,221,(121) & [167,169] other props in .Refs 1 & 5. Its three mononitro
 B 37

derivs are described in the literature: 2-Nitro- ~ Benzaldehyde-nitroph enylbydrazone, 0zN.C~H4a

-benzaldebydeoxime-O-picrylether, pale yel prisms NH. NCH.C6H5. Three isomers are described in
(from aq acet), mp 157-8°(dec) (Refs 2 & 5); 3-Nitru Beil 15,455,461,470, (127,129,132) & [178,182,187]
-@benzaldehydeoxime-O-picryletber, pale yel 2-Azidobenza[debyde-(4-nitrophenylh ydrazone),
crysts(from acet), mp 169° (dec) (Refs 3 & 5) and 02N.CsH4.NH.N:CH.CGH4 .N~; mw 282.26, N
4-Nitro-fi-benzaldeby deoxime-O-pic~letber, pale
29.78%. Orn-red ndls(from ale), mp 191-2°(dec)
yel prisms(from acetone), mp 168° (dec) (Refs 4 &
moderately sol in. hot amyl ale, hot benz or hot
5). Prepn and other props are given in the Refs.
ale; diffc sol in Iigroin. Can be prepd from 2
These compds are probably mild expls
-azidobenzaldehyde and 4-nitrophenylhy drazone
Re/.s: l)Beil 7,[ 170] 2)Beil ~, [189] 3)Beil ;,
hydrochloride in alc soln. It is probably a mild
[195] 4)Beil 7, [200] 5)L.Brady & L. Klein,JCS expl
127,846~7(1925) Re/s: l)Beil 1!5,471 2)E.Bamberger & E.Demuth,
Ber 34,1335(1901)
Benzaldehydephenylhydrazone and Derivatives
Mononitrobenzaldeh yde-nitroph enylhydrazone,
Benzala%hydepbeny2hydrczzone (called BenZyliden
02 N. CsH4.NH.N:CH.C6 H4.N02; mw 286.24,
-phenylhydrazin; Benzal-phenyl-hydrazin or 13enz-
N 19.58%. Nine isomers are described in Beil
aldehyd-phenyIhy drazon in Ger),
15,455,461-2,470,(127,133) & [178,182,188]
CeH~.NH.N:CH.CGH5, mw 196.24, N 14.28%, is
Dinitrobenzaldeby de-nitiopbenylb ydrazone,
described in Beil 15, 134,(31)&[ 57] 0zN.CGH4.NH.N:CH. C6H~(N02)2, mw 331.24,
2-Azido- benzaldehydeph erzylbydrazone,
N 21.14%. Three isomers are described in Beil
C5Hs.NH.N:CH.CeH4 .N9, tllW 237.26, N 29.52%;
15,470,(127,133) & [188, 189]. These compds are
yel prisms(from ale), mp 101.5-102°; readily sol in probably mild expls
benz, hot ligroin and ale; prepn in Ref 2 2,4,6.Trinitrobenzaldehyde.(4.nitrophenylhydra”
Re/s: l)Beil 15,138 2) E. Bamberger & E. Demuth, zone), 02N.C6H4 .NH.N:CH.C6Hz(N02 )~; mw
Ber 34,1335(1901)
376.24, N 22.34%. Bright-red ndls(from hot acet);
4-Azido- benzaldehydepheny lbydrazone,
mp 247°; easily “sol in et acet or MNB; v sl sol
CeH5.NH.N:CH.CGH4 .N3, mw 237.26, N 29.52%;
in ale, chlf or glac AcOH. Can be prepd from 2,4,-
straw-coIored crysts(from methanol), mp 190°(al-
6-trinitrobenzaldehyde and 4-nitrophenylhydrazone
th’ough effervescence begins at 1200); readily sol as described in Ref 2. Its expl props were not in-
in acet, benz, et acet or chlf; prepn in Ref 2 vestigated
Re/s: l)Beil 15,(33) 2)M.D.Forster a H“M”Judd~
Re/s: l)Bei.1 15,471 2) F.Sachs & W. Everding,
JCS 97,260(1910) Ber 36;961(1903)
Berzzaldebyde-fN-ni troso-pbenylhydrazone),
C6H5.(NO).N:CH. C6H3; mw 225.24, N 18.66%, is Benzaldehyde.dinitrophenylhydrazone
described in Beil 15,(104)
and Derivatives
Mononitro benzaldebydepb enylbydrazone, Benzaldebyde-(2, 4-dinitrophenylhy drazone),
C19HI ,N30Z, mw 241.24, N 17.42%. Three isomers (02 N)2C6H3 .NH.N:CH.C6H5; mw 286.24, N 19.58%.
are described in Beil 15,136,137,(32,33) & [58,59]
is described in Beil 15,491 & [217]
Dinitrobenzaldeby depbenylbydrazone,
Monorzitrobenzaldeby de-(2, 4-dinitrophenylby drazone),
Cl sHtoN404~ mw 286.24, N 19.58%. Two isomers (02N)2C6H3.NH.N: CH.C~H~(N02)2; mw 345.257
are described in Beil 15, 138,(33) & [59]
N 24.34%. Three isomers ~e described in Beil 15>
2,4,6~Trinitroben zaldehydephenylh ydra zone,
491 & [217]
CeH~.NH.N:CH.CGHz(N02 )3; mw 331.25, N Dinitro&enzaZdebyde-(2, 4-dinit~pheny~by drazones)~
21. 14%. Red-brn ndls, mp 202°; easily sol in
(02 N)2C6H3.NH.N:CH. C6H3(N02)Z; mw 376”24~
hot acet & in AcOH; very diffc sol in ale, eth N 22.34%. TWO isomers - described in Beil 15~
or benz. Can be prepd from benzaldehyde and
[217]
phenylhydtatine in ACOH soln. It is probably a
2,4,6.Trinitrobenzaldehyde.(2,4.dinitrophenyl.
mild expl
hydrazone),(02N)2 C6H3 .NH.N:C”H.C6H2(N02 )~;
Rels: l)Beil 15,138 & (33) 2)F.Sachs & W.
mw 421.25, N 23.28%. Orn-red ndls, mp 208°.
Everding, Ber 36,960( 1903)
Was prepd by Chattaway & Clemo(Ref 2) but
the method of prepn was not described. Its expl
Benzaldehyde.Nitrophenylhydrazone and
props were not detd
Derivatives
Re/.s: l)BeiI 15,[217] 2)F.D.Chattaway &
 B 38

G. R.Clemo,JCS 123,3061(1923) gas(Refs 1 & 2)

Re/.s: l)Beil 15,( 166) 2)M.Busch & W. Dietz,Ber
Benzaldehyde. trinitrophenylhydrazone 47,3288(1914) & CA 9,806(1915)
and Derivatives Benzaldehyde.p.tolylhydrazone Peroxide, CH~
Benzaldebyde-(2, 4, 6-tn”nitropbenylby drazone), C6H4.NH.N— cH0c6H5; mw 242.27,
(02 N)aC6H2.NH.N:CH. C6H5; mw 331.24, N 21.14%, \M/
is described in Beil 15,495 & [222] O ;3.2 1%; sulfur-yel fidls(from benz+petr eth),
Mononitrobenzaldehyde.(2,4,6.trinitrophenyl mp 77-8 °(dec); readily sol in ale, eth, benz or
hydrazones, (02N)3C6H2.NH.N: ~. C6H4.NOz; chlf; diffc sol in petr eth. It can be prepd by
mw 376.24, N 22.34%. Two isomers are described shaking benzaldehyde-p-tolylhydrazone in
in Beil 15,495 Iigroin, or better in benz soln, with a sl excess
2,6.Dinitrobenzaldehyd.(2,4,6.trinitrophenyl. of hydrogen peroxide. This compd expl sponta-
hydrazone) or 2,6 Dinitrobenzalde.hyde.picryl. neously at RT when dry. Friction or impact does
hydrazone, (02 N)3CSH2.NH.N:CH. C~H~(N02)2; not cause it to ezplode(Refs 1 & 2)
mw 421.25, N 23.28%. Yel ndls(from acet+w), Re/s: l)Beil 15,(155) 2)M.Busch & W. Dietz,
mp 219-20°(dec explosively); diffc sol in aIc, Ber 47,3284(1914 & CA 9,806(1915}
acet & gIac AcOH; nearIy insol in berm Can
Benzaldehyde.semicarbazone and Derivatives
be prepd from 2,6-dinitrobenzaldehyde and picryl-
hydrazine. Its expl props were not investigated Benzaldehyde-semicarbazone(called Kohlensiiure
Re/s: l)Beil ]5,[222] 2)K. vonAuwers & E. Frese, -amid-benzalhydrazid; B enzalsemicarbazid;
Ber 58,1372(1925) Benzaldehyd-semicarbazone or l-Benzyliden-
semicarbazid in Ger), C6H5 .CH:N.NH.C0.NH2;
Peroxide Derivatives of Benzaldehydephenyl. mw 163.18, N 25.75% is described in Beil 7,
hydrazone 229,(126) & [1731
Benzaldehydephenylhydrazone Peroxide, C6H; Mononitroberzzaldeby desemicarbazones, 02N.-
.NH.N —CH.C6Hs; mw 228.24, 0 14.02%; C6H4 .CH:N.NH.C0.NH2, mw 208.18, N 26.96%.
‘ o— */ Three isomers are described in Beil 7,250,255,
yel ndls(from benz+petr eth); mp 65-66 °(dec); 261,(138,140, 143) & [190,196 & 2021
defgr spontaneously; readily sol in benz, ale, Dinitrobenzaldeby de-semicarbazones, (02 N)2-
eth or chlf; diffc sol in petr eth. Can be prepd by .C6Ha.CH:N.NH.C0. NH2; mw 253.18, N 27.66%.
shaking benzaldehyde-phenylhydrazone in benz Two isomers are described in Beil 7,265,(144)
soln with hydrogen peroxide. The comp decompos- & [206]
es explosively on contact with H2S04 2,4,6. Trinitrobenzaldehyde.semicarbazone,
Re/s: l)Beil 15,(32) 2)M.Busch & W. Dietz,Ber (02N)3C6H2.CH:N.NH. C0.NH2; mw 298.18,
47,3281(1914) & CA 9,805-6(1915)
N 28.19%; It yel plates(from AcOH); MP 2140
3.Nitrobenzaldehydephenylhydrazone Peroxide,
(d cc). Can be prepd from 2,4,6-trinitrobenz-
C+ NH.N.O # H. C6H4.N02; mw 273.24,
— aldehyde in alc arid the hydrochloride of semi-
O 23.42%; yel ndls(from benz), mp 83-4°(dec); carbazone in the presence of coned Na acetate
very sol in eth; sol ale; diffc sol in petr eth, dec soln. This compd turns dk-red in a warm dil
in alcoholic soln at RT and in benz at 40-50° NaOH soln and separates unchanged by the addn
evolves Nz. Can be prepd by introducing O in a of an acid. Its expl props were not investigated
Re/s: l)Beil 7,265 2) F. Sachs & H. Kanrorowicz,
benz soln of 3-nitrobenzaldehyde-phenylhydra-
Ber 39,2760(1906)
zone(Refs 1 & 2). It is probably a mild expl
Re/s: l)Beil 15,(33) 2)M.Busch & W. Dietz@er
Benzaldoxine, See Benzaldehydeoxine
47,3287(1914) & CA 9,806(1915)
Benzaldehydephenylbenzylhydrazone Peroxide,
Benzalthiocarbazinic Acid Azide. See 2-Benzyl-
C6Hs .CH2.N(C6Hs).N— CH.C6H5;
‘o-o’ idene-thio-c arbazo yl A zide
mw 318.36, 0 10. O57O; citron-yel ndls(from benz+
petr eth), mp dec ca 70-1°; readily sol in ale, Benzamide and Derivatives
eth or benz; diffc sol in petr eth. This compd very Benzamide; Benzoylamide; Benzene Carbon Amide
quickly turns brn when dried in air and dec ia a or f3enzoic Acid Amide(called Benzamid or Benzol-
short time. Its solns dec on warming, evolvlng s%ure-amid in Ger), C6H~ .C0.NH2; mW 12 L 13,
 B 39

N 11.56% is described in Beil 9,195,(96)& [163] props in Refs

2-Azidobenzamide, N~CeH4.C0.NH2; mW 162.15, Refs: l)Beil 9,386,397(156,164)& [254] 2)P.
N 34.56%; ndls(from w), mp 135.5-136°; sol in ale, Oxley et al, JCS 1946,770-1 3)P.Oxley et al,
glac AcOH, chlf, hot w, or hot benz; diffc SOI in JCS 1947,1114 4)P.OxIey et al, JCS 1948,308
eth. Its prepn and other props are given in Refs Nitrobenzamidine Picrates, (02N)c6H4.C(:NH).-
R efs: l)Bei19,418 2)E.Bamberger & E. Demuth, NH2+C6H2(C)H) (N02)~; mw 394.26, N 21.32%,
Ber 35,1889(1902) nitro-N 14.2%. Two isomers are known: 3-Nitro-
Mononitrobenzamide, 02 N. C6H4.C0.NH2; mw benzamidine PiCrate, yel trysts, mp 228-9° and
166.13, N 16.86%. Three isomers are described 4-Nitrobenzamidine Picrate, yel trysts, mp 239
in the literature: 2-Nitrobenzarnide, ndls(from dil -40°. These compds are probably mild ezpIs
ale), mp 174-176 .6°(Ref 1); 3-A~itrobenzamide, COI Re/s: 1) Beil- not found 2)P.Oxley et al, JCS
ndis, mp 140-3°, bp 310-15°. This compd was 1946,771 3)P.Oxley et al, JCS 1947,1114
prepd in 1848 by heating ammonium-3 -nitrogen- Dinitrabenzamidines, (02N)2CeH3. C(:NH).NH2.
zoate; this reaction sometimes resulted in ex- One isomer, 3,5 -Dinitrobenzamidine, was isolated
plosions. It can be prepd safely by a number of by Oxley et al as the picrate(see next item)
other methods (Ref 2); 4-Nitrobenzamide, ndls 3,5.Dinitrobenzamidine Picrate, (02N)2C6H3.Ce
(from w), mp 197-201.4° (Ref 3) (:NH).NH2+C6H2( OH)(N02)~;mw 439.26, N 22.33%,
Re/s: l)Beil 9,373,(152) & [246] 2)Beil 9,381, nitro-N 15.94%; trysts, mp 271°. This compd is
(155) & [252] 3)Beil 9,394 & [271] undoubtedly expl, but it was not investigated
Dinitrobenzamide, (02 N)2C6H3 .C0.NH2; mw from this point of view
211.13, N 19.90%. Two isomers are described in Re~s: l)Beil- not found 2)P.Oxley et al,JCS
the literature: 2, 4- Dinitrobenzamide, pale-green- 1948,30P
ish ndls(from hot W)$ mp 203-4°; prepd by heating
2,4-dinitrobenzonitrile with dil H2S04 (Ref 1) and
Benzamidoanisole and Derivatives
3, 5-Dinitrobenzarnide, lfts(from w), mp 177-183°;
Benzamidoanisole; Benzamiside or Metboxybenz-
diffc sol in cold w, more readily sol in hot w;
anilide [called Benzamino-phenol-methy l~ther;
prepd by reacting 3,5-dinitrobenzoic acid ethyl
Benzoes~ure-(o- or p)-anisid; Benz(o- or p)-anisid
ester or 3,5-dinitrobenzoyl chloride with NH3(Ref 2)
or Benzamino-anisol in Ger],
Z?e/.s: l)Beil 9,412 2)BeiI 9,414
C6H5. C0.NH.C6H4.0.CH9, mw 227.25. Two iso-
2,4,6.Trinitrobenzamide, (02N)3C6H2.C0.NH2;
mers are described in Beil !3,373,469 & [174,249]
mw 256.13, N 21.88%; yel crysts(from acet+petr
Mononitrobenzamidoanisole,
eth+benz), mp 264°(dec); prepd from 2,4,6-trinitro-
02 N. C6Ha.C0.NH.C6H4 .0.CH~; mw 272.25, N
benzoyl chloride and 50% NH8 soln. its expl props
10.29%. Three isomers are described in Beil 13,
were not detd
390,391,522 & [288]
Re/s: l)Beil 9,418 2)P.J.Montagne,Rec 21,382
Benzamido-dznitro anisole,
(1902)
C6H5.C0.NH.C6HZ(N02 )2.0.CH3; mw 317.25, N
Benzamidine and Derivatives 13.25%. Two isomers are described in Beil 13,394,
Benzamidine or Benzylamidirre, C6H5 .C(:NH).NH2; 526 & (188)
mw 120.15, N 23.32%, trysts, mp ca 80 0. Prepn
Nitrobenzamido-ni tioanisoZe, OZN.CS Ha .CO”NH-
and props in Refs
f?e~s: l)Beil 9,280,(129) & [199] 2) R. P.HuHin .C6H~(N02).0.CH3; mw 317.25, N 13”25~. ‘hree
et al, JCS 1947,395 isomers are described in Beil 13,(186, 187)
t3enzamidine .Picrate, C7HeN2+C6H~N307; mw Nitrobenzamido-dini &oanisole, 0ZN.C6H4 .CO.
.NH.C6H2(NOZ)2.0 .CH3; mw 362.25, N 15.47%.
349.26, N 20.05%; yel ndls, mp 228-33 . Can be
prepd by evaporating a chloroformic soln of an Four isomers =: described in Beil 13,530 &
equimolecular mixt of benzamidine and picric ( 188, 189)
acid Benzarnido- trini~oaniso~e, CSH5 “CO”NH”C6’-
Re/s: l)Beil 9,283 & [199] 2)R.P.Hullin et al, (N02)3.0.CH3; mw 362.25, N 15”47%” ‘rwo ‘sOm-
JCS 1947,395 ers are described in Beil 13,(196,197)
Nitrobenzamidines, (02 N).CaH4 .C(:NH).NH2; Nitrobenzamido.trinitroanisoles, ‘2N”C6’4“cO-
NH. C~H(N02)9.0.CHg; mw 407.25, N 17.20%.
mw 165.15, N 25.45%. Two isomers are known:
3-Nitrobenzamidine, yel prisms(from ale), mp 89° Three isomers are described in the literatwe:
and 4-Nitrob enzamidine, ndls, mp 215 0. Prepn & 4-(2’ -Nittobenzamido)-2, 3, 5-tn”ni tro-anisole,
 B 40

ndls(from ale), mp 25 5°; sol in hot AcOH or ale; Benzanilide; Pbenylbenzarnide or Ben zoylaniline
nearly insol in benz. Can be prepd by heating (called Benzas; ure-anilid in Ger), C6F$ .NH.CO&
p-anisidine of Z-nitrobenzoic acid with nitric- C6H5; mw 197.23, N 7.10%. is described in Beil
acid(d 1.52). Its expl props were not detd (Refs 12,262,(199) & [152]
1&2) Nitrosobenzanilides, C13H1 ON202; mw 226.23, N
4’-(3‘-N!itrob enzamido)-2,3, .5-trinitro-anisole, 12.38%. TWO isomers are described in the Lit-
ndIs(from MNB), mp 247°; sol in hot AcOH, alc erature: 2-A!itrosobenzanilide, C6H5 .NH.C0.C6-
or acet; insol in benz or ligroin. Can be prepd H4 .NO, CO1 crysts(from acet), mp 171°. Its prepn
by heating p-aniside of 3-nitrobenzoic acid with and props are described in Beil 12,267 and
nitric acid(d 1. 52) or by other methods. Its expl N-Nitrosobenzanilide, C6H5.N(NO).C0.C6HS;
props were not detd (Refs 1 & 2) ndls(from eth), mp 67 °(Ref 2); 75-6°(Ref 3);
4’-(4 ‘-Nitrobenzarnido)-2,3, .5-ttinitro-anisoIe, exp on heating; readily sol in eth diffc sol in
ndls(from Lif)YoAcOH), mp 253°; v sol in acet; ale. Can be obtd by shaking benzenediazonium
sol in HN03 (d 1.4} diffc sol in ale. Can be prepd chloride with benzoylchloride and NaOH or by
by heating the p-aniside of 4-nitrobenzoic acid other methods
with nitric acid(d 1.52). Its expl props were not Refs: 1) Beil 12,582 i% [295] 2) A.Wohl,Ber 25,
detd 3632( 1892) 3)H.von Pechmann & L. Frobenius,
Re/s: l)Beil 13,(196) 2)F.Reverdin,Ber ~,2364 Ber 27,653(1894)
-66( 19 11) Mononitrobenzanilide, C ,3H1 oN203; mw 242.23,
Note: Higher nitro derivs were not found in J3eil N 11.57%. Three isomers are described in Beil
or in CA thru 1956 12, 692,704,720,(342) : [380,391]
Dinitrobenzanilide, Cl ~H9N305; mw 287.23*
Benzomidobenzene. See Benzanilide N 14.63%. Two isomers are described in Beil
12,268 & [1531
Benzamidophenol and Derivatives Benzdinitroanilide, (02 N)2C6H3.NH.CC). C6H5;
Benzamidopbenol or Benzoylaminopbenol( called mw 287.23, N 14.63%. One isomer is described
Benzamino-phenol in Ger), CGH5.C0.NH.C6 Ha .OH; in Beil 12,754 & [363]
mw 213.23, N 6.57%. Three isomers are described Nitrobenzonitroanilides, 0zN.C6H4 .NH.C0.C6-
in Beil 13,372,416,469,(1 15, 165) & [ 174,249] H4 .N02; mw 287.23, N 14.63%. Seven isomers
Mononitrobenzatnidopbenol, 02N.CS Ha .CO.NH.- are described in Beil 12,692,704,(342,347,352)
C~H4.0H; mw 258.23, N 10.85%. Four isomers are & [391] and one isomer is described by w. B.van
/lescribed in Beil 13,372,373 & [469] Horssen,Rec 55,252(1936) & CA 30,5198-9(1936)
B enzamidomononitrophenol, C6 H5.C0.NH.C6 H3- Nitrobenzdinitroanilide.s, (02N)2C6H3.NH.C0.-
(N02).0H; mw 258.23, N 10.85%. Two isomers C6H4.N02; mw 332.23, N 16.87%. Two isomers
are described in Beil ~3,390 & [195] are described in Beil 12> 754 & 755 and one iso-
B enzamidodinitropbenol, C6 ~ .C0.NH.C6H2- mer is described by W. B.van Horssen, Rec 55$
(N02)2.0H; mw 303.23, N 13.86%. Two isomers 249( 1936) & CA 30,5 198-9(1936)
are described in Beil 13,396 & 528 Dinitroberzznitroanilide, 02 N.C6H4 .NH.C0.C6H3-
3,5.Dinitro.4.(3'.nitrobenzamido).phenol, 02 N-
(N02). One isomer, the 3,5-dinitrobenz-(4’-nitro-
.C6Ha .C0.NH.C6H2(N02 )2.0H; mw 348.23, N
anilide), is described by W. B.van Horssen,Rec
16.09%. Wh ndls(from ale), mp 215.5°. Was ptepd 55,252-3(1936) & CA 30,5198-9(1936)
by treating O, N-bis(3-nitrobenzoyl}(3 ,5-dinitro
Trinitrobenzarzilide$ CGH5.NH.C0.C6H2 (N02)3;
-4-aminophenol) with cold Na hydroxide soln.
mw 332.23, N 16.87%. One isomer, the 2,4, 6-tn’-
It is probably a mild expl
nitro-, is described by I. Tanasescu & I. Nanu,Ber
Re/’s: l)Beil 13,530 2)R.Meldola & J.G.Hay,JCS
72B, 1092(1939) & CA 33,5827(1939)
91,1479(1907)
B enztrinitroanilide, (02 N)aC6H2.NH.C0.C6 H5;
mw 332.23, N 16.87%. One isomer, the B enz-2,’4j-
5.(Benzamidotriazeno).tetrazole. Same as Benzoyl
6’-trinitroanilide, is described in the literature
-tetrazol yl-isotetrazene
Refs: l)Beil 12 [423] 2)W.Borsche, Ber 56B,
1940( 1923) & CA 18,533(1924) 3)N.M.Cullinane
Benzamiside. Same as Benzamidoanisole
et al, JCS 1932,2364 & CA 26,5925-6(1932)

Benzanilide and Derivatives

Dinitrobenzdinitroanilide, (02N)2C6H3.NH.CO-
 B 41

.C6H~(N02)2\ mw 377-23, N 18.57%. The isamer BENZENE AND DERIVATIVES

3, 5-dinitrobemz-(2’, 4’-dinitrounilide), pale yel Benzene, Benzole, Pbenyhydride, Cyclobexatrienq
crysts(from AcOH), mp 2 13°; readily sol in acet Phene (called Benzol in Ger) ~H’CH-CH
& warm AcOH; diffc sol in ~C or benz; insal in CH=c”H~~ ;
petr eth or chlf, can be prepd by nitration of 3,- mw 78.11, N 7.74%; COI, VOI, flare Iiq; mp 5.5°,
5-dinitrobenzaniIide with abs nitric acid at .15°.
bp 80.1e, fl p 12*F, d 0.8794 at 20°; Q~ at 25°
Its expl props were not detd
(Hzo Iiq) 789 kcaI/mol; vap press 100mm at
Refs: l) Beil- not found 2)W.B.vaI-I Horssen~Rec
26.1°; S1 sol in w(o.6% at 200); miscl in all
55,251(1936) &CA 30,5198-9( 1936)
propns with ale, eth, acet or glac ACOH; sol in
most org solvs. The vapors of benz are extremely
Benzanilide-Diazonium Derivatives
toxic and exposure may induce acute or chronic
1.Benzanilide.4.diazoniumhydroxide or Benzamino-
poisoning. The max allowable concn for 8 hr ex-
benzene-4 -diazoniumhyhoxide [called l-Benz-
posure is 35ppm in air or 112g/m ‘. its volatility
amino-benzoldiazoniumhy droxyd-(4) or N-Benzoyl
-anilin-di azoniumhydroxyd-(4) in G er], C6H$ .CO- and flammability make ir a potential fire hazard,
so great care must be exercized in its handling
tNH.C6H4 .N(~N).OH; mw 241.24, N 17.42%. This
and transportation. Air contg more than 1.3~ benz
compd is known only in the form of its salts, some
will propagate a flame; 1.4 to 8% in air(by vol) is
of which are expl, such as: Cblon”de, Ce% .CO-
an expl mixt(Refs 4 & 8)
.NH.C6H4.N2.C1, COI trysts, mp- dec ca 139°;
Benz(crude) is obtd comly by fractnl distn of
readily sol in w or ale; insol in eth. It can b,e
light oil, which in turn is formed as a by-product
obtd by treating N-benzoyI-p-pheny Ienediamine
in the high temp destructive distn of coal; it is
hydrochloride with amyl nitrite in AcOH soln and
obtd from coke oven gas, carburated water gas,
pptg the salt with eth; Perchlorate, C6H5.C0-
and by the cracking of gasoline under press and
.NH.C6H4.N2.C104, CO1 crysts(from w) which turn
elevtd temp(Ref 7)
yel on exposure to light; mp expl on heating, It
Benz is the parent compd of a series of aromat-
can be prepd by treating the chloride with KC104 ic hydrocarbons from which many of the most im-
in warm aq soIn and cooling the mixt to ppt the
port expls ate derived. Benz is an excellent SOIV
perchIorare. This compd also expl on impact or
from which many expI intermediates can be prepd.
percussion
Its di-, tri-, and tetra- nitrocompds are expls
Other salts, such as the nitrite, acetate, carbon-
R e/s: l)Beil 5,179,(95) & [1 19] 2)Thorpe 1
ate, theocyanate, picrate, etc, many of which dec
(1937),667-75 3)USBurMinesBull 279,78(1939)
on heating, were also prepd and described by
4)MfgChemAssocn, ”Safety Data Sheet SD-2”( 1946)
Morgan et al(Refs I, 2 & 3) 5)Kirk & Othmer 2(1948),420-42 6)T. E. Jordan,
Refs: l)Beil 16@604 2)G.T.Morgan & F .M.Mickle- “Vapor Pressure of Organic Compounds”, Inter-
wait,JCS 87,933(1905) 3)G.T.Morgan & M. AIcock,
science, NY( 1954), Chapt l,P 19 7) Faith~Keyes
JCS 95,1323(1909)
& Clark(1957),138-46 8)Sax(1957),342-4
l.Benzanilide.3.nitro.4.diazoniumchloride [called Benzene, Analytical Procedures. Benzene can be
3-Nitro-l-benzamino-benzol.di azoniumchlorid-(4)
detected by conversion to m-dinitrobenzene (using
or N-Benzoyl-3-nitro-anilin-diazoniumchIorid in
for nitration equal vols of fuming nitric acid and
G er], C6H6.C0.NH.C6H~ (N02).(jN).Cl; mw coned sulfuric acid) and subsequent identification
304.69, N 18.39%; yel-wh lfts of the dihydrate, of the latter compd(Refs 3 & 9).
mp expl mildly on heating. It was prepd by di- .A Brit test for detection of benz in air involves
azocizing N4-benzo yl-2-nitro- 1,4-phen yl enediamine the absorption of the vapor in coned sulfuric acid
with NaN02 + HC1 (Refs 1 & 2) contg formaldehyde; an orange-brown color is pro-
Refs: l)Beil 16,608 2)C.B~low & E. Mann,J3er duced even with traces of benz(Ref 9,P 525).
30,984(1897) Elkins(Ref 10,P 283) describes the socalled Per-
nitrite test, which consists of adding to a small
Benzazide. See BenzoylAzide under Benzoic sample 2ml of aq Na nitrite soln & 2ml 2N sul-
Acid furic acid, shaking, adding 2ml 3% hydrogen sul-
fide and shaking again. After waiting lmin, apel-
Benzazimidol or Benzohydroxytriazole. See under let of KOH is added and if benz is present a red
Benzotriazole and Derivatives -brn coloration forms around the pellet
For the quantitative detn of benz many methods
 I

have been proposed. One of the most accurate Diazidobenzene, N3.C6H4.N3; mw 160.14, N
methods is the Smyth modification of the m-dinitro- 52.48%. rwo isomers are described in the lit-
benzene-reduction method, using titanous chloride erature: 1,3-Diazia’obenzene, yel ndls, mp 5°,
soln. This method is described in detail by Jacobs dec on steam bath; dec in coned H2S(Y4 with
(Ref 9,p 531-6) and briefly described here under the appearance of flame and a S1 deton. It was
Dinitrobenzeae. A more rapid but Iess accurate prepd by treating a soln of m-phenylenediamine
method is the m-dinitrobenzene-butanone method in 50% H2S04 with NsN3 and diazotizing with
described in Refs 4 & 5 and in Ref 9.pp 527-29. Ns.Nz(Refs 1 & 4). Kleinfeller(Ref 5) reported
Its modifi cations are described in Ref 9,PP 529-31 that the action of m-C6H4(N3 )2 upon BrMgC?C-
(See also Ref 7). Still another but less accurate MgBr gave an amor yel compd, C8H6N6, which
method, which is simple and may be performed in exploded on heating and 1,4-Diazidobenzene,
the field, is the oxidation method in the presence It yel tablets(from eth), mp 83°, expl extremely
of hydrogen peroxide and iron salts. This method
violently on heating; readily dec by heating on
is described by Cook & Kicklen(Ref 2) and by steam bath; readily sol in eth or chlf; diffc sol
Jacobs(Ref 9,pp 537-9) in ale; insol in w. It was prepd from p-amino-
According to Elkins(Ref 10,p 283), the amt of
azidobenzene by diazotization, conversion to
benz can be estimated approx from the refractive the diazoperbromide and thence to the diazido
index of the fraction of distillate contg benz. The
c omp(Refs 2 & 3). Also see Ref 6
method is applicable if only hydrocarbons are Re/s: l)Beil 5,279 & [209] 2)Beil 5279
present
3)0.Silberrad & B. J. Smart, JCS891,171(1906)
A microcolorimetric method for detn of benz in
4)M.O.Forster & H. E. Fierz,JCS 91 11,1953(1907)
air is described by Elkins(Ref 10,pp 284-6) (see
5)H.Kleinfeller,, JPraktChem 119,61-73(1928) &
also Ref 8). Detn of benz in urine is described
CA 22,2566(1928) 6)S.Maffei & L. Coda,Gazz 85,
in Ref 10,p 369 1300-3( 1955) & CA 50,9330( 1956)
Refs: l)Beil 5, 196,(106-7) & [145-6] 2)W.A.Cook Azidomononitrobenzene, 02N. C6H4.N3; mw 164. 1~
& J. B. Ficklen, IEC,AnalEd 4, 406(1932) 3)W.P.
N 34. 14%. Three isomers (all explosive) are de-
Yant et al, USBurMinesReptInvest RI 3282(1935) scribed in the literature: l. Azido-2-nitrobenzene,
4)H.H.Schrenck et al, USBurMinesRI 3287(1935)
yel ndls(from benz+alc); mp 51-3°; readily sol in
5)S.J.Pe~ce et al, USBurMinesRI 3302(1936)
ale, glac AcOH or benz; sol in eth. Its prepn is
6)W.P.Yant et al, USBurMinesRI 3323(1936) 7)R.H.
given in Refs 1 3 & 4); 1 -Azido-2-nitrob enzene,
Dolin,IEC,AnalEd 15,242(1943 ) 8)H.D.Baetnstein,
col ndl s(from dil ale), mp 52-5° ~ dec by heating
IEC,AnalEd 15,251(1943) (photometric dete~in-
on steam bath; readily sol in ale, eth, benz, or
ation of benzene, toluene and their nitro deriva-
CS2, insol in W. Its prepn is given in Ref 1; 1
tives) 9)J acobs(2949),524-39 10) Elkins( 1950),
-Azido-4-nitro-benzene, CO1 lfts(from dil de),
282-6 & 369
mp 71-4°, dec by heating on steam bath; v read-
ily sol in hot ale, eth, benz, glac AcOH or C di-
Azido and Azidonitro Derivatives of Benzene sulfide; diffc sol in cold w. Its prepn is given in
Azidobenzene (called Azidobenzol, Triazobenzol, Ref 2
Phenylazid or Diazobenzolimid in Ger), C6HS .N9; Re/s: l)Beil 5,278 2)Beil 5,278,(143) & [209]
mw 119.12, N 35.28%; pale yel oil with odor like 3)P.A.S.Smith & J.I-LBoyer, Org Synth 31, 14-16
bitter almond; mp expl on distn at normal press; (195 1) 4)S.Maffei & L. Coda,Gazz 85,1300-3
thermochem props(Ref 5} S1 sol in alc or eth; in- (1955) &CA 50,9330(1956)
SOI in w. Many methods of prepn are listed in Ref Azidodinitrobenzene, (02N)ZCGH3.N3, mw 209.12,
1. Treatment with A1C13, in absence of SOIV, re- N 33.49%. Only the l-Azido-2,4-dinitro-benzene
sults in an expln(Ref 4) is described in the literature; It yel, almost CO1
Rets: l)Beil 5, 276,(141) & [207] 2)0. Turek, ndls(from diI AcOH), mp 57-8° & 65-9Q, e#odes
Chim & Ind(Paris), Special No, 833-7(June 1933) on heating rapidly; readily sol in most SOIVS; in-
& CA 28,750(1934) 3)R.O.I.indsay & C. F. H. Allen, SOI in w. Its prepn and other props are given in
C)rg Synth 22, 96-8(1942) & CA 36, 579(1942); Org- Refs 1 & 2
Synth Coil Vol 3, 710-11(1955) 4)W.Borsche & McNutt(Ref 3) used the Pb salt with Ba(NOs )z.
H. Hahn, Chem Ber 82, 260-3(1949) & CA 44,1101 as a priming compon mixt, and instead of the pb
( 195o) 5)P .Gray & T. C. Waddington, PrRoySoc salt, he proposed alk & alkaline earth salts of
235A, 481( 1956) & CA 50, 15203( 1956) azidodinitrobenzene with LA, Ba(N03 )2, Sb2S~,

1
 B 43

Pb sulfocyanate & ground glass as priming com- It is an extremely sensitive expl

pns (Ref 6). McNutt(Ref 4) also prepd priming Ref.s: l)Beil- not found 2)Blatt,0SRD 2014(1944),
mixts contg the Pb salt G Ag tetracene, and azido- listed under Nitro Compounds
d initrobenzene with basic LSt and other ingred- l,3,5.Triazido.2,4.dinitro.benzene, (02N)2C5H-
ients such as BaK nitrate double salt, Sb2S3, (N3)3, mw 291.16, N 52.93%, OB to C02 -46.7%.
Ca sililicide & ground glass(Ref 5). Kelson (Ref Crysts(from ale), mp 116-7°(dec); compd turns
7) patented the use of the K salt as an ingredient brn at 50° and becomes semi-liq; insol in w; sol
of priming compns in conduction with MF, Pb in acet or boiling ale, SI sol in cold ale. A comp
hypophosphite, K2Ba(N03)4 & Sb2S3 prepd by Friederich and called “dinitrotriazido-
Re/s: l)Beil 5,279& [209] 2)G.Powell,JACS benzene*, without identifying the position of the
51,2438( 1929) 3)J.McNutt,USP 1906394(1933) & groups, was probably the same as the l,3,5-tri-
CA 27,3612( 1933) 4)J.D.McNutt,USP 1930653 azido-2,4-dinitro-benzene which was later prepd
(1933) & CA 28, 328(1934) 5)J.D.McNutt,USP by Turek(Ref 3) by refluxing dinitro-dichloro- or
2002960( 193 5) & CA 29,4944(1935) 6) J. D. McNutt, tribromo-benzene in aq acetone with alc Na azide.
USP 2005197(1935) & CA 29,5274( 1935); BritP Friederich(Ref 2) proposed the use of his compd
432096(1935) & CA 30,618(1936) 7)V.J.Kelson, as an expl chge alone or with other ingredients
Australian P 104189(1938) &CA 32, 8782(1938) in percussion caps, detonators, etc
1•Azid~2,4,6.trinitr~ knzene or P icrylazide Refs: l)Beil- not found 2)W.Friederich, GerP
(called 2.4.6-Trinitro-diazobenzolimid or Pikryl- 531253(1931) & CA 25,5565(1931) 3)0. Turek,
azid in Ger), (02 N)3C6H2.N3, mw 254.12, N Chim&Ind Special No, pp 883-7(1933) & CA 28,
3 3.07%; yel prisms(from abs ale), mp 89-93° 750( 1934)
(dec); SOI in ale, benz, or chlf; insol in Iigroin
or petr eth. One method of prepn is by reacting l,3,5.TRlAZlDO.2,4,6.TRlNlTRO.BENZENEor
equi-mohr quants of picryl chloride with NsN3 2,4,6.Trinitro. l,3,5.triazido.benzene ( abbr as
in aq alc soln. Other methods of prepn and props TATNB or TNTAB), (02N)3CG(Na)a; mw 336.16,
are given in Refs 1, 2, 3 & 4 N 50.00%, OB to C02 -28.6%. Grn-yel crpts, mp
This compound is more sensitive to impact 131° (dec with formn of hexanitrobenzene); crystal
than tetryl; it detonates on S1 impact. it is an d 1.805; pressed d at 42000psi 1.75, at 3000kg/cm2
expl more powerful and bris,ant than TNT (power 1.7509 and at 5000kg/cm2 1.7526 (Ref 6aX Q: 840
139% & brisance 132% TNT). it is unstable and kcal/mol(Ref 4b); 2554cal/g(Ref 8); readily sol in
loses N when heated acet; mod sol in chlf; SI sol in alc and insol in w.
Refs: l)Beil 5,279,(144) & [209] 2 )E.Schrader, It is non-hydroscopic and does not attack iron, steel,
Ber 50, 777(1917) 3)H.Rathsburg, GerP 341961 copper or brass. On exposure to light, its color
(1921) 4)A.Korczynski & St.Namyslowski, BuII deepens. No change took place in 3 years storage
Fr 35, 1186-94(1924)& CA 19,644(1925) of TNTAB under water(Ref 6a)
1,3(or 4,6) -Diazido-4,6(or 1,3)- dinitro-.benzene, It was first prepd in 1923 by Turek on treating
(02N)2C6H2(N~)z, mw 250.14, N 44.80%. Yel 2,4,6-trichloro-1,3,5-trinitrobenzene with an alkali
pltlts, mp 78°; expl violently when heated a- azide in ale, acet or w soIn. It can be obtained
bove the mp. Was prepd by treating diniuodi- also from aniline by chlorination to sym-trichloro-
chlorobenzene with Na azide in mixt of acetone, aniline, followed by diazotization, treatment with
alc & w (Ref 3) alc to give sym-trichlorobenzene, nitration with
McNutt (Ref 2) considered a mixt of diazido- mixed nitric-sulfuric acid to trinitrotrichloro-
dinitrobenzene and tetracene with Ba(N03)z, benzene and finally treatment with an alc soln of
Sb#9,Pb02 & ground glass as a suitable prim= Na azide(Refs 3,5,6a & 8)
ing mixt for small arms Properties of TATNB. When ignited in the open,
R efs: l) Beil- not found 2)J .D.McNutt,USP it burns rapidly with a dazzling blue flame. When
2009556( 1935) & CA 29,6429-30(1935) 3)R.J. dead-pressed(ca 3000kg/cm2), it either burns
Gaughran et al, JACS 76, 2235(1954) & CA 49, when ignited or puffs weakly(Ket 6a). When con-
6238(1955) fined(even slightly, as in detonators) it expl
1,3. Diazido.2,4,6.trinitrasbenzene or Picryldiazide, when heated in a flame. A violent deton takes
(02N)3CeH(N~)2, mw 295.14, N 42.72%, OB to place when TATNB, compressed in a metal tube,
C02 -35.2%; yel trysts, mp 92°. Was prepd by is heated
heating a soln of picryl dichloride with Na azide. Behavior ‘Toward Metals was detd by Ficheroulle
 B 44

& Kovache(Ref 6c,p 15~ Burning Rate 0.65c~sec ~c 208A, 188( 1951) & CA 46,5845(1952) 7a)Stett.
(Ref 6b); DeadPressed ca 42000 psi, d 1.75(Ref bacher,P61voras (1952) 8)PATR 1740, Rev 1(1958),
8); B risance by PIate Punching Test is ca 158% 340-3, & OrdCorpsPamphlet ORDP 20-177(1960),
TNT(Ref 6a); Explosion Temperature 150°(10secs) 283-5
(Ref 8); Figure of Insensitiveness(FI). See under
Impact Sensitiveness; Friction Sensitiveness. Al- Azido.Halogen Derivatives of Benzene
though reported in some literature as “relatively Azidoiodosobenzene, N3.C6H4.10; mw 261.02, N
insensitive=, it is not always true as the experi- 16. 10%. Three isomers are described in the litera-
ence at PicArsn has shown. When a tryst sample ture: l-Azido-2-iodoso- benzene, softens ca 85°,
of TATNB was carefully diminuted to 50-IOO(US mp 90-100°(dec) (Ref 1) l-Azido-3-iodoso benzene,
Std Sieve) in a flat agate mortar using a very yel amor mas., mp-expl ca 125° and its Formate,
small portion at a time(ca 0.2g), one of the por- expl ca 78 °(Ref 2); and l-Azido-4-iodoso benzene,
tions vigorously detonated with evoln of flame. expl on heating to 130° or on contact with coned
No detons took place when a hardwood mortar HN03 or coned H2S04; its Cbremate, a dk-red
and pestle were substituted; Hygroscopicity: mass, expl by friction or heating to 7 1°; and its
practically non-hygroscopic(Refs 6a,6c & 8); Formate, expl ca 85 °(Ref 2). The prepn and oth-
Ignitability of Compressed Pellets was studied er props of these iodoso-azido compds are given
by Schmitt(Ref 6); impact Sensitiveness:FI 6%PA; in the Refs
W~hler Apparatus 60% positive at 30cm vs 7 .5cm Refs: l)Beil 5,(142) 2)Beil 5,(143) 3)M.D.Forster
for MF; ButMines App, 2kg wt 25cm(Refs 6a & & J. H.Schaeppi,JCS 101 II, 1362-3(1912)
8) (see also Ref 6c); Initiating Action: Log Of Azidoiodoxybenzene, N3.C~Ha.102; mw 277.02,
commercial TNT compressed at 500kg/cm2 re- N 15. 17%. Three isomers are described in the
quired 0.02g TATNB(compressed at 300kg/cm2] literature: 1-Azido-2-iodoxy-benzene, brownish
for complete deton, while only O.Olg is required ndls(from glac AcOH), expl violently by friction
to deton l.Og of Tetryl(Ref 6a}, Power by Trauzl or on heating to 157 °(Rei 1); l-Azido-3-iodoxy
Test: 179% TNT at d I.@ 152%PA and 90%PETN -benzene, brownish ndls(from w or glac AcOH);
(Ref 6a); Sand Test Valtie- not found; Volubility expl ca 175-80°(Ref 2) and l-Azido-4-iodoxy-bm-
in various solvents was detd by Ficheroulle & zene, ctysts which rapidly become brown, expl
Kovache(Ref 6c,p 15); Thermal Decomposition ca 170° or on contact with coned H#04(Ref 2)
was studied by Tutek(Ref 4) and then by Yoffe Refi l)Beil 5,(142) 2)Beil 5,(143) 3)M.0.
(Ref 7); T hermal Stability. It is fairly stable at Forster & J.I-LSchaeFpi,JCS 10I II, 1365(1912)
below the mp, but when melted it is converted l.Azido.2,4.dichlora.benzene, N3.C6H3C12; mw
to hexanitrosobenzene; Uses: Turek(Ref 2) pat- 188.02, N 22.35%; yellowish ndls(from ale) or
ented the use of TATNB as a primary expl. It can prisms(from acet or benz), mp 5 l-4°(dec at 160°
be press-loaded at ca 3000kg/cm 2(Ref 6a). SFM- on prolonged heating); sol in ale, benz, eth, chlf
CTG, FrP 893941(1944) & CA 47, 8374, patented or petr eth; insol in w. This compd expl on rapid
its use as a component of priming compns Fiche- heating or by strong impact, generating much
rouIle & Kovache (Ref 6c) examined i= props smoke, and when completely dry, it expl on heat-
for use in priming compns ing below its mp. The prepn and other props are
Refs: l)Beil- not found 2)0. Turek,BritP 298629 given in Beil 5, [208]
and 298981(1927) & CA 23, 3101(1929> Gerp
498050( 1927) & GerP 494289(1928), CA 24,2886 Nitroso and Nitronitroso Derivatives of Benzene
& 3904(1930) 3)0. Tutek,Chim&Ind(P aris) 26,781 Nitrosobenzene, C6H5 .NO; mw 107.11, N 13.08%;
(125T)(1931) & CA 26,848( 1932) ;PicArsn Transla- COI crysts(from alc+eth), mp 67.5-8° to an emerald
tion No 70 by H. VOOS( 1960] Chim & Ind 29,883 -grn liq; readily sol in nearly all SOIVS with the
(1933 ) 4)0.Turek, Chim & Ind Special NO,PP 883- solns immedy turning an emerald-grn color. Many
7(1933) & CA 28,750(1934) 4a)Stettbached 1933), methods are known for the prepn of nitrosoben-
329 4b)A.Schmidt,SS 29,263(1934) 5)Davis( 1943), zene but the principal ones are by the oxidn of
436 6)R.Schmitt,SS 38,133(1943) & CA 38,2822-3 the amine and of the N-substituted hydroxyl-
(1944) 6a)Blatt,0SRD 2014(1944) 6b)A.F.Belya- amine. Various other props and chemical re-
ev & A.E. Belyaeva,DoklAkadN 52,503( 1946) & actions of nitrosobenzene are described in Beil
56,491(1947); CA 41,4310(1947)& 44,8109(1950) 5,230,( 123) & [1691
6c)H.Ficheroulle & A. Kovache,Mp 31,15-16 & 26 Dinitrosobenzene, C6H4(NO)Z; mw 136.11> N
(1949) & CA 46,11687(1952) 7)A.D.Yoffe)prRoy-
 UB45

20.58%. Two isomers are described in the lit- component of primary compns
erature: 1,3-Dirzitrosobazene, yel crysts(from Re/s: l)Beil 5, [202] 2)W.Friederich, BritP
alc+eth), mp 146. 5°; readily sol in ale, benz or 192830( 1921) & JSCI 42,332A(1923) 3)W.Borsche,
hot glac AcOH; mod sol in Iigroin; diffc sol in Ber 56,1498(1923)
eth; insol in w. The melted mass and the solns 2,4,6Trinitr-l.nitrosobenzene,( 02N)3C6H2 .NO;
are colored grn(Ref 1) mw 242.11, N 23. 14%; grn-yel Ifts(from glac Ac-
1,4-Dinitrosohenzene, dk-yel, mp- at 184° begins OH), mp 198°; dec on contact with coned HN03.
to turn brn and at 245°, compd is completely Can be prepd by oxidn of 2,4,6-trinitrophenyl
darkened; dec at temp of steam bath; diffc sol hydroxylamine with Cr trioxide in ACOH soln
in most org soIvs(Ref 2). The prepn of the di- (Refs 1 & ~). ~ts expl props were not investigated
nitroso compds is given in the Refs Refs: l)Beil 5,276 2)R.Nietzki & R.Dietschy,
Refs: l)Beil 5, 232 2)Beil !5,~[171] Ber 34,59(1901)
Hexanitrosobenzene, ON.~C(NO)=$.NO ; mw Dinitrodinitrosobenzene, (02 N)2C~H2(NO)2; mw
ON. C-C(NO)=C.NO 226.11, N 24.78%. The 4, 6-Dinitro- l-2-dinitroso-
252.14, N 33.35%; trysts, mp 195°; was claimed benzene is the only isomer described in the lit-
to be obtd by Turek(Ref 2) when sym-trinitrotri- erature: crysts(from ale), mp 172 0, dec by ex-
azidobenzene(qv) was heated above 131° in xy- posure to Iight. This compd appears to have been
lene. According to BIatt(Ref 3), this compd has first prepd by Rathsburg(Ref 3) and later by
an Impact Sensitiveness,FI, 26% PA; a Lead Korczyiiski & Namyslowski(Ref 4) by heating
Block Expansion value 178% PA, and, although p icryl chloride in alc at 100° with aq NaN~.
not a primary expl, it is equal to Tetryl as a Rathsburg(Ref 3) called this compd 1,3-dinitro-4t.
booster. This compd is not listed in CA indices >-dinitrosobenzene and prepd its K, Na and Pb
R efs: l)Beil- not found 2)0. Turek,Chim & Ind salts which were proposed for use in detonators,
(Paris) 26,785( 129T)(footnote)( 193 1) &CA 26, Mixts suitable as a top(prirnary) chge in detona-
848(1932) 3)Blatt,0SRD 2014(1944) tors consisted of the K salt o/ dinitrodinitroso-
Mononitronitrosobanzene, OzN.csH4.N~, mw benzene and the diffc sol salts of hydrazoic
152.11, N 18.42%. Three isomers are described acid, tetrazole derivs$ etc(Ref 2). Boyer &
in the literature: 2-Nitro-l-nitiosobazene, yel Schoen(Ref 6) studied the reduction and other
-wh crysts(from et acet or acet), mp 126-126.5°, reactions of this compd which they called 1, 5-di-
turns grn at ca 120°; readily sol in hot chlf, hot nitro-2, 3-dinirrosobenzene. Blatt(Ref 5) lists
benz or hot ace~ mod sol in hot alc or hot ligroin; this compd as 1, 3-dinitro-4, j-dinitrosobenzen e
diffc sol in eth and nearly insol in petr eth or w. I?e/s: l)Beil- not found 2)H.Rarhsburg,BritP
The solns are colored intensively grn(Ref 1); 177744( 1921~ CA 16,3399(1922) & JSCI 41,441A
3-iVitro- I-nitrosobenzene, COI ndls, mp 89.5-91° (1922) 3)H.Rathsburg,BritP 190844( 1921); CA
to a grn Iiq; readily sol in hot ale, chlf, acet or 17,2960(1923) &JSCI 42,332A(1923) 4)A.
glac AcOH; diffc sol in eth; almost insol in petr Korczyiiski & St. Namyslowski,BullFr 35,1186
eth(Ref 2} 4-Nitro- l-nitrosob enzene, lt yel ndls -94(1924) & CA 19,644(1925) 5)Blatt,0SRD
(from ale), mp 118-9-l@ to a. grn ljq; readily 2014(1944) 6)J.H.Boyer & W.Schoen, JACS 78,
sol with a grn color in benz, chtf, glac AcOH, 423-5(1956) & CA 50,13017(1956)
acet or hot ale; mod sol in Iigroin; diffc sol in Note: Compare with info on Dinitrobenzofuroxan
eth; nearly insol in w(Ref 3). The “mononitro- under Benzofuroxan and Derivatives
nitrosobenzenes are volat at the temp of a steam
bath. Their prepn is given in the Refs Nitro-Derivatives of Benzene
Refs: l)Beil 5,256 2)Beil 5,257 & [192] 3)Beil Mononitrobenzene(MNB) or Oil of Mirbone (called
5,257 & [192-3] Nitrobenzol or Mirba@ in Ger), C6H5.N02; mw
2,4.Dinitro.l.nitrosobenzene, (02N)ZC8H3.NO; 123.11, N 11.38%; It yel oil, mp 5.6-5.7°, bp 210°
mw 197.11, N 21.32Yo; dk-yel ndls(from glac -9°, vap press 0.262 mm Hg at 20°(Ref 10), d
AcOH), mp 133° to a dk-grn liq; sol in warm 1.205 at 18°; Q: 740kcal/mol(Ref 3) or 6033
ale, glac AcOH or benz with a grn-colored soln; cal/g(Ref 5); readily sol in ale, eth or benz; S1
dec in warm NaOH soln. Can be prepd by treat- sol in w(o.19% at 200). MNB is toxic and its
ing fi-[2,4-dinitrophenyl] - hydroxylamine with MAC in air is lppm or 5mg per m3 of air(Ref 11).
cold chromic acetate(Refs 1 & 3) It represents a moderate expln hazard when ex-
Friederich(Ref 2) patented the use of the posed to heat or flame(Ref 11). Its thermal de-
Basic Pb salt of dinitronitrosobenzene as a compn was studied by Condit & Haynor(Ref 8)
 1

B 46

MNB was first prepd in 1827 by Mitscherlich to C02 -95.2%. Three isomers, o-(or 1,2-), m-(or
on treating benz with fuming nitric acid. A bet- 1,3-) and p-(or 1,4-), can be obtd on nitration of
ter way is to nitrate benz with mixed nitric-sul- MNB but in accordance with the Crum-Brown-Gib-
furic acid(Refs l&4). Details of a lab procedure son rule the substitution of the second N02 group
are given by Davis(Ref 7) takes place chiefly in the meta position; hence
The expl value of MNB is very low but when only small quants of the ortho and para DNB are
mixed with oxidizing agents, such as nitric acid found in the coml product:
or nitrogen peroxide, it produces very powerful Ortho. or l,2.Dinitrobenzene (I,2.DNB), COI
expls(see Sprengel Explosives, Helhofite, etc). monocl prisms, ndls(from w or AcOH), tablets
It has been reported(Ref 9) that Al chloride (from ale, benz or chlf); mp 117-8°, expl when
added to MNB contg 5% phenol caused such a heated in a test tube to 472 0, bp 319° at 774mm
rise in temp that the mixt exploded. During WWI Hg, d 1.59 at 18°, Q: 703kcal/mol(Ref 7) or Q;
some airplane bombs contd two compartments 4194cal/g(Ref 14); very sol in chlf or et acet;
separated by a thin partition; one compartment sol in benz(5.7% at 180); sl sol in alc(I.9% at
contd MNB and the second contd liq nitrogen 210), and diffc SOI in w(O.01% in cold w). This
peroxide. On impact with the ground the parti- compd can be steam distd. 1,2-DNB appears to
tion broke and the two Iiqs mixed, forming an have been known since ca 1874 and can be prepd
extremely powerful expl which was detonated by nitration of benzene(or MNB ) or by the re-
by a fuze. As early as 1881, Turpin proposed a action of o-nitroaniline nitrate with Cu sulfate
shell using MNT & liq N204 in separate com- and Na nitrate. Other methods of prepn are given
artments(Ref 3a).During WWII, Roth(Ref 6) in in Ref 1. Ortho-DNB is usually present in coml
Germany, proposed a mixt of equal proprns of DNB but the principle constituent is 1,3- or meta
MNB, NG & TeNMe. This mixt possessed 117% -DNB. For toxicity see Ref 29
the power of NG; according to Trauzl Test re- Meta or 1,3.Dinitrobenzene (1,3.DNB); COI rhmb
sults. Another mixt, consisting of 22.5 MNB trysts, mp 88-91°, expl when heated to 580°, bp
and 77.5% TeNMe, had the following character- 302° at 770.5mm Hg, vap press I.lmm Hg at 110°
istics: d 1.68, Power- 117%NG or about equal (Ref 27), d 1.57 at 20°, Q: 699.8kcal/mol(Ref 7)
to PETN, Sensitivity to Impact- same as for or Q: 4155cal/g(Refs 11 & 14); sol in benz(39.5%
NG, and VeI of Deton- (max) 7700m/sec at d
at 18°) or in abs alc(3.3% at 200); SI sol in cold
1.68(Ref 6)
w, chlf or et acet; can be steam-distd. According
Peters(Ref 2) patented a blasting expl con-
to Colver( 1918),p 18, it was first prepd in 1834
sisting of MNB 4, AN 75, nitrated potato meal
by Mitscherlich, but the earliest Ref in Beil 5,
20 & asphalt 1% (See also Anilithe Vol IPA442-R)
528, is the paper of Deville(ca 1840). Mets-DNB
Re/s: l)Beil 5,233,(124) & [171] 2)G.M.Peters,
can be prepd by nitration with mixed nitric-sul-
USP 1048578(1912) & CA 7,703(1913) 2a). Mar-
furic acid of either MNB or benz. Details of prepn
shall 1(19 17),253 2b)Colver( 19 18), 117-137
are given by Stettbacher(Ref 12) and the lab prepn
3)W.E.Garner & C. L. Abernethy,PrRoySoc 99A,
by Davis(Ref 21). Other methods of prepn and
213-35(1921) & CA 15,3748( 1921) 3a)Marshall
props are described in Refs 2,6,15 & 16. A com-
3 (1932), 51, 71, 99& 176 4)Stettbacher( 1933),
prehensive description of numerous additive
255-6 5)A.Schmidt,SS 29,262(1934) & CA 29,
products of 1,3-DNB is reported by Karv6 & Sud-
3841(1935) 6)J.F.Roth,ss 36,4, 28 & 52(1941) borough (Ref 8) and by Khaishbashev & Gromova
& CA 35,5317( 1941) 7)Davis(1943), 133 8)P.C.
(Ref 26). The bydroxylamine Na metbylate salt,
Condit & R. L. Haynor,IEC 41, 1700-4( 1949) &
C6 H806N4Na2, It red trysts, expl mildly on heat-
CA 43,9045(1949) 9)Anon,C&EN 3 1,4915(1953)
ing or on contact with w (Ref 40,p 2537)
& CA 48,1684(1954) 10)T.E.Jordan, ”Vapor Pres-
Para. or l,4.Dinitrobenzene (l,4.DNB), CO1 mono-
sure of Organic Compounds”, Interscience,NY
clinic prisms, ndls(from ale), mp 173.5-174°; can
( 1954),Chapt 7,pp181 & 194 ll)Sax( 1957),944
be heated in a closed test tube to 360° without
l,2)E.Leclerc & F. Devlaminck,BuIICentreBelge- decompn; bp 299° at 777mm Hg, vap press 1.6mm
HtudeDocEaux(Li?ge), No 14,246( 195 l/IV)
Hg at llOO(Ref 27), d 1.625 at 18°, Q: 692.9kcal/
(Toxicity of MNB and DNB’s found in the waste
mol(Ref 25) or Q: 4146cal/g(Ref 14); sol in eth;
waters of expl plants)
SI sol in w or ale; can be steam distilled. Para
-DNB appears to have been known since 1874
DINITROBENZENE (DNB)(Called Dinitrobenzol
(Rinne & Zincke), when it was obtd in small
in Ger) C6H4(N02)2; mw 168.11, N 16.67%, OB
quants by nitration of benz. It can be prepd in

—
 B 47

75% yieId from p-nitroaniline, Amm persulf ate The Japanese also used DNB in some compos-
and H2S04 in the presence of AgNOa. Other ite expls, such as Sh?ibenyaku or Anbenyaku
methods of prepn are given in Refs 3 & 20. P ara (Ref 23). DNB has also been used as a Constitu.
-DNB is present in small quants in coml DNB. ent of some coml expls together with other aromat-
The AJa salt, C6H404N2Na2, red trysts, deton ic nitrocompds and AN or K perchlorate(see Bel-
mildly when heated(Ref 4a,p 2529) lite, Perdite and Roburite), and in some dynamites
DNB, Commercial, yel oil, mp ca 85°, consists to lower die fr p of NG(Ref 18). When used alone,
of about 93.5% m-DNB, 6.4% o-DNB and O. 1% DNB reqd a large amt of booster chge to effect
p-DNB(Ref 15). A method of separating isomeric its detonation (Ref 6)
DNB’s to obtain pure m-DNB has been patented The Russians used DNB quite extensively
by Coward(Ref 17). DNB is a HE which is ex- either straight(for cast-loading) or in mixts with
tremely toxic having an effect similar to that of other substances, such as AN (in Bellites), PA,
TNT. It is absorbed thru the lungs and di- TNX, TNT, etc. The K-1 Splav (K Cast Mixture)
gestive tract and may effect vision heart action used during WWII for filling sorm cast-iron land
and nervous reflexes(Refs 9,15 & 23). Several mines consisted of DNB 30 & TNT 70%(Ref 23a)
cases of intoxication in ammo plants from ex- Refs: l)Beil 5,257,(135) & [193] 2)Beil 5,258,
posure to DNB causing methemoglobinemia (135) & [193] 3)Beil 5,261,(136)& [195]
have been reported(Ref 24). Because of its 4)W.Will,SS 1,209(1906) 4a)J.Meisenheimer &
toxicity, the use of DNB was forbidden in France E. Patzig,Ber 39,2529& 2537(1906) & JCS 90 I,
(Ref 15) and it was replaced in expl compns by 642 & 653(1906) 5)H.Kast,SS 8,174(1913)
DNT. The toxicity of DNB has also been ex- 6)Marshall 1(1917),256 6a)Colver( 1918),138-145
amined and described by other investigators 7)W.E.Garner & C.A.Abernethy, PrRoySoc 99A,
(Refs 19& 28) 213/35(1921) & CA 15,3748(1921) 8)D.D.Karv6
Explosive Properties of DNB (Refs 4,5,13 & 22): & J .J.Sudborough,JIndInstSci 4, 159-76( 192 1) &
Ballistic Strength, 88% TNT; Brisance by Sand CA 16,65(1922) 9)J.Stukowsky,SS 18, 14-6(1923)
Test, 32g sand crushed vs 43g for TNT or ca 82% 10)(? ) Bu1ov,SS 23,170(1928) 1 l)W.I-I.Rinkenbach,
TNT; by Copper Block Compression Test ca 80% JACS 52,116(1930) 12)Stettbacher ( 1933),20,
TNT; Explosion Temperature, does not deton 257-8 & 363 13)L.Wohler & O.Wenzelberg,Ang
from exposure to heat up to 360 0; Heat of Com- Chem 46, 173(1933)& CA 27,2579(1933) 14)A.
bustion, Q: 698kcal/mol or 4160cal/g; Heat o~ Schmidt,SS 29,262(1934) 15)Pepin L Shalleur
Explosion, Q: 870cal/g; Jmpact S ensitivity, (1935), 161-2 16)Vennin,Burlot & L6corch6( 1932),
18” vs 14- for TNT, Pic Arsn App with 2-kg wt 409 17)H.W.Coward,USP 2040123(1936) & CA 30,
or ca 135% TNT; Power by Trauzl Test, 85% 4512( 1936) 18)Thorpe 4(1940),465 19)W.F.von
TNT; Rifle Bullet Sensitiv?~, no detonations Oettingen,USPubHealthServBull ~ 1( 194 1),94-103
from impact of a cal 0.30 bullet fired at 90ft; & CA 36,4596(1942) 20)OrgSynth Col Vol 2(1943),
Stability, completely stable and does not attack 225 21)Davis(1943), 133-4 22)Blatt,0SRD 2014
metals; Temperature Developed on Explosion, (1944) 23)All&EnExpl(1946), 111 & 157 23a)
2500°; Velocity of Detonation, ca 6100m/sec Schilling( 1946),240 24)M.Glahn & P .Schack-Schou,
at d 1.50 NordiskMedicin(Stockholm) 36,2 135-6( 1947) & CA
Uses. DNB was used extensively by the Ger- 42,4756( 1948) 25) J. L. Franklin,IEC 41, 107 O(1949)
mans during WWI, mostly in admixture with TNT. 26)0. K. Khaishbashev & V.E .Gromova,IzvestSektora-
It was claimed that such mixts were nearly as Fiz-KhimAnal,InstObshchei i NeorgKhimAkadNauk
powerful as TNT alone(Refs 10,23 & 30). Its 17, 144-8(1949) & CA 45,2762(1951) 27)T.E.Jorda~
use in France was prohibited by the Commission “Vapor Pressure of Organic Compounds”? Inter-
des Substances Explosives because of its toxici- science,NY( 1954),Chapt 7,181 & 193-4 and Plates
ty. Dinitrotoluene was used instead of DNB(Ref 14 & 16 28)(?) Kiese,Explosivst 1954,24 29)SSX
15). Due to the shortage of TNT in Germany dur- ( 1957), 629 30)PATR 2510 (PB No 161270)(1958),
ing WWII, DNB was again used extensively alone pp Ger 36-R & 47;R 3 l)E.Leclerc & F. Devlaminc~
or in admixt with AN, RDX, Hexanitrodiphenyl- BullCentreBelge-EtudeDocEaux(LiGge),No 14,246
anrine and other expls. DNB acted to desensitize (1951/IV) &CA 46,10507(1952) 32)PATR 2510
other expls and it made some mixts suitable for (PB No 161270) (1958),P Ger 36-R(Dinitrobenzol)
cast loading. German Amatol type Fillers No 52 TRINITROBENZENE (TNB) (Called Trinitro-
and 52A. using DNB, AN and othet additives, are benzol in Ger), C~Hg(N02)3; mw 213.11, N 19.72%,
listed in Ref 30 OB tO C02 -56.3%. Three isomers are known and
 I

B 48

described in the literature(the 1,3,5- or sym-TNB This compd is reported by Blatt(Ref 33) to exist
deriv is the most important one in the expI in- in at least three polymorphic forms. The stable
dustry): form crystallizes at RT as orthorhombic plates
l,2,3(or 1,2,6). Trinitrobenzene ( 1,2,3.TNB), CO1 and flat rods
lfts with grn cast(from abs aIc), mp 127°; SI SOI l,3,5-TNB was first prepd by Hepp(Ref 3,p 345)
in alc; insol in w. It was first prepd in a pure in 1882 by nitrating m-DNB with strong mixed
state by Korner & Contardi(Ref 10) from dinitro- nitric-sulfuric acid. Claus & Becker(Ref 4) pro-
benzenediazonium nitrate and NsN02 in the pres- posed preparing sym-TNB by oxidg TNT with fum-
ence of a Cu saIt. Other methods of prepn are ing nitric acid to trinitrobenzoic acid and heating
given in Ref L This TNB is unstable, especially in w to eliminate C02. A better method is to oxid-
in regard to the 3rd nitro group which is easily ize TNT using K or Na bichromate and coned sul-
hydrolyzed or otherwise removed furic acid(Refs 21,31,32 & 36). Sym-TNB may also
l,2,4(orl,3,4)-Trinitrobenzene(l,2,4.TNB), COI be prepd by reduction of picryl chloride with Cu,
lfts(from eth) or lt-yel prisrrrs(from dil ale), mp as proposed by Desvergnes(Ref 19). According to
60-2°, d 1.73 at 16°; Q: 676kcal/mol(Ref 17) or Pepin LehaIleur(Ref 25), the yields for the differ-
3185cal/g(Refs 23 & 27); sol in benz, eth, chlf, ent methods are as follows: by direct nitration of
MeOH or ale; insol in w. It was first prepd in M-DNB, 5W0; by oxidn of TNT with chromate mixt,
1882 by Hepp(Ref 3,p 34) by nitration of p-dinitro- 73%; and by reduction of picryl chloride, 60%. A
benzene with a mixt of fuming nitric-sulfuric lab method of prepg sym-TNB is given by Davis
acids. Other methods of prepd and props are (Ref 32,p 135). Addnl info on the prePn of sym
given in Refs 1 & 2 -TNB may be found in the following Refs(5,7,12,
l,3,5(or2,4,6)orsym.Trinitrobenzene(sym.TNB) 16,18,20a,29 & 34)
(caIled Bepzite in Fr), COI Ifts(from a large amt TNB, Commercial, yel trysts compd, mp 120-20,
of boiling w), mp 121-122 .5 °(stable form), 61° d 1.67, consists principally of 1,3,5-TNB. It is
(unstable form) (Ref 16); expl on rapid heating; considered to be a more powerful and brisant
d 1.688 at 20°, Q: 659.6 to 665.6kcal/mol(Refs HE than TNT but it is more sensitive to impact
17,23 & 27). The dielectric constants of sym-TNB than TNT, based on the following:
and associated substs have been detd by Schurz Explosive and Other Properties(Refs 6,8,9,11,13,
et al(Ref 37). Its sol in various SOIVS is as fol- 14,15,19,20,22,24, Brisarzce by Sand Test,
& 33):
lows(Ref l,p 203): 110% of TNT; by Lead Plate Cutting Test, about
equal to PA; by Lead Block Compression Test,
Solubility of sym.TNB(g in 100g Solvent 111% TNT and by Copper Cylinder Compression
Solvent at 17° at 50° Test 114% T~; Explosion temperature, 520°;
Heat o/ Combustion, Q: at 17°, 3096cal/g(Ref
Water 0.028(15°) 0.102 28); H~at of Explosion, 1063caI/g; Hygroscopicity>
Ether 1.70 2.72(32.5°) at 25°, gains 0.05% at 100%RH; Impact Sensiti-
Carbon disulfide 0.239 0.44(330) vity, FI 109% PA or more sens than TNT and less
Chloroform 6.24 18.42 sens than PA; 11” vs 14” for TNT on Pic Arsn
Carbon tetrachloride 0.237 0.69 Impact App; impact ,Work, for 50% explns with
Benzene 6.18 25.70 2kg wt, 12mkg/cm2 or 106%TNT; Power by Bal-
Toluene 11.82 76.31
listic Mortar, 105- 17%TNT; by Lead Block Ex-
Methanol 3.76 7.62
pansion (Trauzl Test) 108%PA & 111% TNT and
Ethanol 2.09 4.57
by pressure Bomb 110% TNT; Stability, Tb ermal.
Acetone 59.11 160.67
TNB is one of the most stable HE’s. Its sta-
Ethyl Acetate 29.83 52.40
bility by 120° Vacuum Stability Test is 0.46cc/5g
P yridine 112.61 194.23
in 48hrs; by 135°C Heat Test, not acid & no ex-
pln in 300min and by KI Test at 65. s0-85 rein;
Drummond(Ref 18,p 339T) gives a table of set- Temperature Develop ed on Explosion, 35400(max}
ting points of TNB & DNB mixts (see under Ben- and Velocity of Detonation, 7000m/sec at d 1.64;
zene, Analytical Procedures). Sym-TNB is re- 7350m/sec at d 1.66 in 20mm diam paper cartridg-
ported by Sax(Ref 38) to be severe in toxicity re- es; 7440m/sec with cast expl(d 1.68)
sulting either from inhalation or ingestion. The Uses TNB appears to be superior to TNT in many
effects can be both acute and chronic systemic. re spects. If a more satisfactory and economical
 B 49

method for its prepn could be found, TNB might

of info) 41)G.Desseigne, MP 43,7- 13(1961 )( Prepn
be used as a bursting chge in shells and bombs.
of TNB by decarboxylation of TNBAc formed on
Pressed TNB was used by the Germans in WWII
oxidation of TNT with sulfochromic acid)
as Filler No 70 in some primers(Refs 35,34a & 39).
Also, due to the shortage of toluene in Germany
during WWII, a mixt of 60% DNB and 40% TNB TNB Additive Compounds, Complexes and Other
was satisfactorily used in loaded ammo items Derivatives
(bombs) where exudation was not of importarice There exists a large group of tryst complexes
(Ref 39) contg in stoichiometric proportions polynitro
Re/s: l)Beil 5,(140) & [203] 2)Beil 5,271 -aromatic substs, such as TNB or PA, and aro-
3)P.Hepp,Ann 215,345 & 361(1882)& JCS 44, matic hydrocarbons and bases and their derivs.
315-6(1883) 4)Ad.Claus & H. Becker,Ber 16, These complexes are, for the most part, unsta-
1597( 1883) 5)ChemFabrikGriesheim,GerP 77353 ble, and some of them are expl. Some examples
(1893) & SS 9,193(1914) 6)W.Will,SS 1,211-13 of these are the following:
(1906) 7)J. Meyer,GerP 234726{ 1909) & SS 9, 1,3,5- TNB+Sodium Metbylate, C6H3{N02 )3+ 2CH8.
194( 1914) 8)M.H.Dautriche,MP 16,27(1911-1912) ONa; red amor subst, expl violently on rapid
9)H.Kast,SS 8,173(1913) 10)G.K6rner & A. Con- heating to ca 100°(Ref 6)
tsxdi,AttiAccadLin 23 11,464(1914) & CA 9,1478 1,3,5 -TNB+Potasszum Metbylate, C6H3(N02)3+
( 1915)& SS 10, 64-5( 1915,) 1 I)Marshall 1(1917), CH3 .OK+ l/2H20; red trysts, expl violently
258 1 la)Colver(1918),146- 160,2 18,220,536,659, when heated on a Pt foil (Ref 2)
673,689,732 12)M.h4.Kostevitch, ‘{TNT & TNB” 1,3, 5-TNB+ Potassium Methylate+A cetone, C6H~
Pamphlet, Maillard & Co, London(1919),38pp & (N02)3+CH3 .OK+ l/2CH~ .C0.CH3; dk-grn ndls
CA 15,3747(1921) 13) R. L. Datta & N. R. Chatterjee,
(from acet thru eth), stable on heating to 100°
JCS 115,1006(1919) 14)H.Kast,SS 15,172( 1920)
15)A.Stettbacher, SS 16,139(1921) 16)L.G.Rad- but expl at higher temps (Ref 8)
1,3, 5- TNB+Hydrogen Cyanide, C6 H3 (N02 )3 +HCN;
cliffe & A. A. Pollitt,JSCI 40,45-48T & 90T( 192 1)
red ndIs(from aIc or eth), dec ca 175°; the K salt,
& CA 15, 2356(192!) 17)W. E: Garner & C. L. Aber-
nethy,prRoySoc 99A,2 13(1921) & CA 15,3748 KC7H306N4, dk viol tryst mass, expl mildly on
(1921) 18)A.A.Drummond, JSCI 41 ,338-340T heating (Ref 4)
(1922) & SS J7,169-70(1922) 19)M.L.Desvergnes, 1,3, 5- TNB+Hydroxylamine and Sodium Methylatq
C7H, , 09 N6Na3; red, fine-grained trysts contg
MP 19, 221-3(1922) 20)W. M.Dehn & A. A. Wagner,
ArOrdn 8,35(1927) 20a).S.Secareanu,B uIIFrI [4] 2-3 moles H20, expl mildly on rapid heating
51,591-6(1932) & CA 26,5081-2(1932) 21)Stdt- (Ref 7)
tbacher( 1933),162 22)L .Yohler & O. Wenzelberg, 1,3,5- TNB+Pbenylhydrazine, C6H3 (N02)3+
AngChem 46,173(1933)& CA 27,2579(1933) 23)A. Ce H5N2H3, dk-red, long flat prisms which sin-
Schmidt,SS 29,262(1934) 24)A.Majrich & F. Sorm, ter at 75-80° and dec with SI expln (Ref 10)
SS 30,338(1935) 25)Pepin Lehalleur( 1935),162 1,3, 5- TNB+Hydrazine C6H3(N02)3 + 2N2H4; grn
26)Vennin,Burlot & L6corch~( 1932),409 27JE. shiny prisms, mp 122-3 °(dec)~ expI miIdly On
Burlot & M. Tbmas,MP 29,262(1939) & CA 34, heating in a free flame(Ref 10)
1849( 1940) 28)M.Badoche, BullFd [5] 6,57o 1,3, 5-TNB+Sodium Hydroxide, CeH3(N02)3 +
(1939) & CA 33,5736(1939) 29)J.R.Johnson, NaOH; red-brn tryst ppt, expl on heating(Ref 11)
OSRD 160(1941) & PB Rept 31092 30)R.Adams 1,3, 5- TNB+Potassium Propylate. C6H3 (N02)3 +
& C.S.Marvel,OSRD 312(1941)& PB Rept 31095 3CH3 .CH2.CH2 .OK, finely dispersed red, un-
3 l)OrgSynthCollVol 1(1941),543 32)Davis(1943), stable solid, expl (Ref 9)
134-40 33)Blatt,0SRD 2014(1944) 34)H.Aaronson, 1,3, 5-TNB+ .Ethylsodioacetoacetate, C6H3 (N02 )3+
PATR 1562(1945) 35)C.H.Brooks, PBRept 3CH.CH3 .C().Na.C00C2H5; brn-red amor powd,
~2930(1945) 35a)All&EnExpl( 1946),l12 36)M.L. expl on heating (Ref 5)
Kastens & J. F. Kaplan,IEC 42,402( 1950) & CA 1,3, 5- TNB+Ethylsodiomalonate, C6H3(N02 )3+
44,444 1(1950) 37)J.Schurz et al, Monatsh 86, 3CH.Na(COOC2H5 )2; maroon amor powd; expl
986-94(1955) & CA 50,6117( 1956) 38)Sax( 1957), on heating (Ref 5)
1222-3 39)PATR 2510(PB No 161270)(1958), p 1,3, 5- TNB+Acetone and Alkali, reaction gave a
Ger 48 40)M.Blais et al, PATR 2587( 1959), =Prep- blk solid complex which is expl(Ref 12). Similar
atation of Thermally Stable Explosives deval- compds, prepd by one of the authors(BTF) dur-
uation of 2,4 ,6-TNB” (Conf ) (Not used as a source ing WWII, from TNT, acet and aw KOH were found
 B 50

m be expl and in CC14 0.04% at 25°; pyridine dissolves

Complexes of sym-TNB with aromatic hydro- TeNB immedy with a brisk efflorescence and
carbons and amines in CHC13 solns were prepd rise in temp; toluene decomps it even in the
by Bier(Ref 13) who detd their equil constants, cold
enthalpy and energy of formation 1,2,3,5-TeNB was first prepd in 1923 by Borsche
Refs: l)Beil 5,272-3 & (140) 2)C.A.L.de Bruyn (Refs 1 & 2) by heating picrylhydroxylamine with
& F. H.van Leent,Rec 14,150 1895) & JCS 70 I, fuming HN03 on a w bath; later by Holleman(Ref
1478(1896) 3)J.L.Heinke,Ber 31,1398(1898) & 4) by heating picramide with nitric acid satd with
JCS 74 I, 413(1898) 4)A.Hantzsch & H.Kissel, nitrous fumes and by Desvergnes(Ref 5) who treat-
Ber 32,3144(1899)& JCS 78 1,90(1900) 5)C.L. ed 2,4,6-trinitroaniline with nitric acid and purified
Jackson & F.H.Gazzolo,AmChemJ 23,376(1900) the crude product by crystn from ben Z. Earlier de-
& JCS 78 1,433-4(1900) 6)C.L.Jackson & R.B. scriptions of the prepn of TeNB are erroneous
Earle,AmChemJ 29,114(1903) & JCS 841,339 (Ref l,p 276). Pepin Lehalleur(Ref 7) describes
(1903) 7)J.Meisenheimer & E. Patzig,Ber 39, in detail a lab procedure based on HoHeman’s
2539(1906) & JCS 90 1,653(1906) 8)A.Hantzsch method
& N. Picton,Ber 42,2125(1909) & JCS 961,468 Explosive Properties (Ref 8). 1,2,3,5-TeNB is
(1909) 9)M.Busch & W. KOgel,Ber 43,1563(1910) an extremeI y powerful and brisant expl and is
&-JCS 98 1,474(1910) 10) K. A. Hofmann & H. Kirm- more sens to impact than TNT: Impact Sensitiv-
renther, ~er 43,1765(1910); CA 4,2801(1910) & ity, FI 67% PA; by Kast App, 2kg wt. 25cm vs
JCS 98 1,548-9(1910) ll)M.Giua,Gazz4511,35~ 83cm for PA; Power, by Trauzl Test- ca 150%
(1915) & JCS 108 1,885(1915) 12)M.Kim~a, TNT; Stability, no decpmn in 6hrs at its mp temp,
JPharSoc(Japan) 73,1216-23(1953)& CA ~, but the N02 group in the 2 position is readily
12699(1954) 13)A.Bier,Rec 75,866-70(1956) & hydrolyzed
CA 50,16332(1956) 14)M.Blais et aI,PATR l,2,4,5.TeNB, lt yel crysts(from dil ale), mp 188°.
2524(1959), “preparation of Thermally Stable It can be prepd by warming on a w bath 4,6-dinitro
Explosives: 2,4,6-Trinitrobenzene Derivatives - l,3-dihydroxylaminobenzene (or 2,4-dinitro-l ,5-di-
(Conf Rpt, not used as a source of info) hydroxylaminobenzene), C~H2(NHOH)2(N02 )2,
with coned nitric acid (d 1.52)(Ref 3)
Trinitrobenzeneozonaphthalene. See under Ben- Uses: Coml TeNB which is a mixt of the above
zeneazonaphthalene and Derivatives isomers, should be suitable for use in booster
expls or as a secondary chge in detonators. Its
Trinitrobenzeneazonaphthol. See under Benzene- toxicity is not known(Ref 9)
azonaphthol and Deri.vat ives Re/s: l)Beil 5,276,(141) & [ 207] 2)W.Borsche~
Ber 56 B,1942(1923) & CA 18,533(1934); Ber 63B,
Tetranitrobenzene (,TeNB) (called Tetranitro-ben- 1007( 1930) & CA 24,3767(1930) 3)W .Borsche &
ZOI in Ger), C5H2(N02)4; mw 258.11, N 21.7%, E. Feske,Ber 59B, 820(1926)& CA 20,2667(1926)
OB to C02 - 31.0%. Two isomers, both powerful 4)A.F.Holleman,Rec 49,112-20(1930) & CA 24,
expls, are described in the literature: l,2,3,5(or 2440-1(1930) 5)L.Desvergnes, RevChimInd 40,
1,3,4,5*TeNB, yel ndls(from chlf), mp 125-6°, d 34-7(1931) & CA 25,2980-1(1931) 6)E.Hertel &
1.6 1; tryst structure detd by Hertel & Romer(Ref G. H. Rgmer,ZPhysChem [b] 22,277(1933) & CA
6) but erroneously called l,2,4,6-TeNB; readily 27,5228(1933) 7)Pepin LehaHeur(1935),165
SOI in acet or glac AcOH; sol in ale, diffc sol in 8)BIatt,0SRD 2014(1944) 9)Sax( 1957)-not listed
benz or eth. The NaOH soht is red but becomes Pentanitrobenzene, CGHN~Ol ~; its prepn was at-
yel on heating. Desvergnes(Ref 5) reported that tempted by van Rijn(Ref 2) accord-to the method
TeNB is insol in w, but it is decompd by it(even of Borsche(see above) in which the NH2 OH group
in the cold) to PA and HN02. Ale, eth, acet and is oxidized to N02 with abs HN03 but the reaction
other compds contg oxygen decomp TeNB ~d failed to produce the desired product
for this reason can not be used as SOIVS for its Re/.s: l)Beil- not found 2)P.J.van Rijn,Rec 45,
purification, It is necessary to use hydrocarbons 257(1926) & CA 20,2317(1926)
or h alogenated hydrocarbons for this purpose. Hexanitrobenzene, C6N60, *; its prepn was at-
Solubilities of TeNB according to Desvergnes tempted by van Rijn(Ref 2) following the method
(Ref 5) are as SO11OWS:in benz 2.29% at 23°; of Borsche(see above) but the reaction failed to
chIf 0.58% at 23°; carbon disulfide 0.09% at 23°; produce the desired product
 B 51

Re/.s: l)Beil-not found 2)P.J.van Rijn,Rec 45, Elektrochem 53,115-17 (1949)& CA 43,8978(1949)
257(1926) & CA 20,2317(1926) 8)J acobs( 1949),53 1-6 & 722-3 9)Organic An-
alysis, Interscience,NY 2(1954 ),90-1 10)Dr
Benzene, Nitro Derivatives, Analytical Procedures Hans Walter, PicArsn; private communication
Mononitrobenzene(MNB) can be detected and es- (1961)
timated by one of the following methods: a) Aniline Trinitrobenzenes. Of these, only the s(or 1,3,5)
Method consists of treating a MNB-contg sample -TNB is of importance as an explosive. It can be
with Zn-HCl to reduce MNB to aniline and esti- detected and estimated by calorimetric or by
mating the amt of aniline(Ref 8,pp 710 & 722-3) other tests
b)Dinitrobenzene Method consists of treating a Best & Nicholson(Ref 3) describe a method in
MNB-contg sample with mixed nitric-sulfuric acid which ca a O. lg sample is dissolved in 10ml ace-
and estimating the amt of DNB produced as re- tone and 3ml of 5% N aOH soln is added. An in-
sult of the nirration,(Ref8,p 524 & 723) tense red coloration is produced which turns It
Note: No color is produced when an acetonic red on dilution with w and becomes blood red on
soln of MNB is treated with aq NaOH(Ref 5) addn of HC1
Dinitrobenzenes. Of these, only the m-isomer Moss & Mellon(Ref 4) describe a quantitative
is of importance in the expls industry. For its colormetric detn of s-TNB when in m ixrs with m
detection and estimation, there may be used the -DNB. For this, ca a 50-100mg sample is dis-
reduction method proposed by Smyth et al(Refs solved in 50ml of 95% ethanol and an aliquot 0.1
4& 5). In this method the m-DNB is reduced by addg to 1.Omg TNB is withdrawn to a 50ml volumetric
an excess of standard titanous chloride soln to flask. To this is added 0.5ml of 10% NaOH soln
diaminobenzene and the excess of titanous chlor- and then(with shaking) ethanol is added to the
ide is detd by titration with std ferric alum soln. 50ml mark. After allowing to stand for 10 reins,
The following reactions take place: the intensity of coloration is measured color-
C6H4 (N02 )2 + 2TiCl~ + 12HCI ~ C~H4 (NE12)2 + metrically, using a blue-green filter, such as
12TiC14 + 2H20 Corning No 396
Cruse & Haul(Ref 5) describe a polarographic
2TiC~ + 2HCl + Fe2(S04 )3+ 2TiC14 + 2FeSOe+ method of detn of s-TNB. Siggia(Ref 7) and Or-
H2S04 ganic Analysis(Ref 8) describe a titanous chlor-
ide reduction method which is applicable to s
A detailed description of this method in mod-
-TNB. Shriner et al(Ref 9) give the mp of the
ified version, is given by Jacobs(Ref 8,pp 53 1-6)
naphthalene addn compd as 153°, which maybe
A soln of m-DNB produces with NaOH an in-
used for identification of s-TNB
tense red-violet coloration and with ammonia
Drummond(Ref 2) stated that attempts to sep-
rose-red to purple-red(Ref 2)
arate TNB from DNB by fractional crystallisation
Best & Nicholson(Ref 6) dissolve ca O.lg sam-
from alc and CC14 or by fractional pptn from ni-
ple in 10ml acetone and add 3ml of 5% NaOH soln.
trating acids were not successful. More promis-
No color is produced wiih MNB but a purplish
ing results were obtained by formation of compds
-blue color is produced with m-DNB which be-
of TNB+ aniline
comes light purple on dilution with w and yel
A rapid estimation of TNB & DNB contents
-brn on addn of HCI. Cruse & Haul(Ref 7) de-
may be made by detg the setting point of the
scribe a polarographic method of detng m-DNB.
mixt and comparing the value obtained with set-
h-t Organic Analysis(Ref 9) a gravimetric method
ting points given in the following table(Ref 2,
is described for the detn of DNB by weighing
p 339T)
the undissolved tin. This method is not applica-
ble to TNB See Table Following Page
Detns of m-DNB in mixts with s-TNB are brief-
ly described under the next item(see also Ref 3)
Refs: l)Beil 5,240 & [ 179] (Mononitrobenzene)
2)BeiI 5, [ 195] (1,3-Dinitrobenzene) 3)A.A.Drum-
mond,JSCI 41,338T(1922) 4)H.F.Smyth, Jr, JInd-
Hyg 10,163(1928) 5)H.F.Smyth,JIndHyg 11,338
(1929) & 13,227(1931) 6)R.W.Best & F.Nicholson,
IEC,AnalEd 7, 190(1935) 7)K.Cruse & Haul, Z-
 B 52

Setting Points —.—.

of Mixtures . base)
% m-DNB % s-TNB Setting d) Extract the phenylenediamine with benz, e-
Point *C vaporate the solvent and weigh the residue
o 100 Note: Phenylenediamine may be detected as
121
22.4 77.6 Bismarck Brown by treating with Na nitrite
96.3
30.4 69.6 e ) Acidify the phloroglucinate and extract the
85.7
36.9 63.1 free phloroglticinol with ether, evaporate the
75.3
41.2 58.8 solvent and weigh
70.7
44.8 55.2 Note: Another method is to nitrate the residue
64.9
47.0 53.0 to trinitrophloroglucinol, precipitate it as Pb
61.4
49.5 phloroglucinate, weigh the salt and det its m~
50.5 57.2
50.7 R e/s: l)BeiI- no analytical procedures given
49.3 57.8
53.4 46.6 2)A.A.Drummond, JSCI 41,339T 3)R.W.Best &
57.8
57.2 42.8 F.Nicholson,IEC, AnalEd 7,191(1935) 4)M.L.
60.3
62.8 37.2 Moss & M. G. MeHon,IEC,AnalEd 14,806-1(1942)
65.2
71.3 28.7 5)K.Cruse & R. Haul,ZElektrochem 53,115-17
71.5
75.1 24.9 (1949) & CA 43,8978(1949) 6)Jacobs- not found
74.5
80.8 19.2 7)Siggia(1949),84 8)Organic Analysis,lnter-
78.0
87.3 12.7 science, 2(1954 ),73-4 9)Shriner, Fuson & Curtin
82.0
100 0 (1956),324 10)Dr Hans Walter, PicArsn; private
89.5
communication(1961)
Since mp’sbetwn 89.5 and 57.2° represent two
different compns, the one contg an excess of DNB Benzeneazoacetaldoxime,, C6H5.N:N.C(:N.0H)-
and the other contg an excess of TNB, it is nece- CH3; mw 163.18, N 25.75%; orn-yel trysts, mp
ssary to distinguish between them. For instance, 118.5-1 19.5°; readily sol in ale, eth, chlf, benz
if a mixt has a setting point of 71.00, it may con- or boiling Iigroin; diffc sol in petr eth. Prepn
sist of either ca 42% DNB & 58% TNB or ca 70% and other props are given in the Refs. It forms
DNB and 30% TNB. In order to det which of these salts, some of which are expl: Silver salt, AgC~
compns is present, a weighed portion of sample H~NaO, orn trysts, mp- expl ca 80° and Sodium
(ca lg) is placed on a porous plate and the en- s~lt, NaCeH~N30, h yel ndls, mp- expl; ‘very
semble inserted in an oven maintained at 60°, easily sol in w, alc or hot AcOH; insol in eth or
which is slightly above the eutectic temp(ca benz
57.2° ). After about one hour the plate is removed Re/s: l)Beil 16,14-5, (220) & [7] 2)H.Vos-
and the unabsorbed portion of the sample is test- winckel, Ber 32,2485(1899) & 33,2795(1900)
ed calorimetrically for TNB or DNB. In this test 3)E.Bamberger & W. Pemsel,Ber 36,56(1903)
all the eutectic(which is a 50/50 compn) is melt-
ed and absorbed, leaving on the surface of the Benzeneazoacetaldoxime Picrylester (called
plate the compd which is in excess of 50%. The O-Pikryl-benzolazoacetaldoxim in Ger),
unabsorbed portion can be weighed and its mp C6H5.N:N.C(CH3 ):N.0.C6H2(N02)3; mw 374.27,
can be detd
N 22.46%; orn ndls(from benz+ligroin), mp- expl
A t-oore precise procedure for analysis of DNB
ca 140°; easily sol in benz; insol in alc or li-
-TNB mixts, communicated to us by Dr Walter
groin. Can be prepd from the Na sah of benzene-
(Ref 10), consists of the following operations: acetaldoxime and picrylchloride in abs alc soln
a) Treat the TNB-DNB mixt with stannous chlor-
Re/s: l)Beil 16,15 2)H.Voswinckel,Ber 33,
ide in HCI to obtain 1,3,5-triamino- and 1,3-di- 279S(1900) & 35,3271(1902)
amino-benzenes
b) Bring the soln to pH 7 and boil it. This op- Benzeneazo.carboxy.phenyl.triazole
eration transforms the triamine to phloroglucinol and Derivatives
and,leaves the diamine unaltered 4.(Benzeneazo).5.carboxy.2.phenyl.@vic(or2,3,1)
Note: The presence of phloroglucinol can be de- .triazole [ called 5-BenzoIazo-2-pheny l-1,2,3 -tri-
t ected by ferric chloride(blue coloration) or by azol-carbons~ure-(4) or C-Benzolazo-N-phenyl
other phenolic reaction methods -osotriazol-C-carbons &.ue in Ger] ,
c) Make the soln alkaline with KOH. This gives
K phloroglucinate and phenylenediamine(free
C6H5.N:N.C= $
 B 53

mw 293.28, N 23.88%; orn-yel lfts(from SIC or Refs: Same as Refs 2 & 3 above
dil AcOH), mp 195° ; nearly insol in w or li- 3, GDinitrobenzenea zotri nitromethane is describ-
groin; sol in ale, ACOH and many other org ed in Conf US Rubber Co Final Rpt on Contract
solvents. Was obtained, together with other NORD 10129
products, on heating phenylhydrazone of N, Trinitrobenzeneazotrinit~ometbane, C7HzNs0, ~-
N’-diphenylformazy lglyoxylic acid with AcOH not found in Beil or in CA thru 1956
Its Silver salt, Agc, ~H, oN~02, yel solid,
insol in w, is a mild expl and probably so are Benzeneozoaniline. Same as Aminoazobenzene,
the Ba, Cu, Hg and Pb salts Vol l,p A184-R
Re/s: l)Beil 26,342 2)E.Bamberger & J .Mfiller,
Ber 27,152-3(1894) Benzeneazobenzene. Same as Azobenzene, Vol 1,
Azido-C ,5H ,oNe02, ~i=iAC15H9N, ,02, p A646-R
Moqonitro-C, ~H, ~N604, Dinitro-c, ;H9N70~,
Trin~tro-C, ~HaNaOe and Tetra%itro-C ,5 H7N9(3, o Benzeneazodiphenyiamine. Same as Anilinoazo-
~~~~atives were not found in B eil or in CA through benzene, Vol 1,p A420-R

Benzeneazomethane and Derivatives Benzeneazonitroformate. Same as Benzeneazo-

Benzeneazomethane( called Methyl-phenyl-diimid; trinitromethane
Methanazobenzol or Benzolazomethan in Ger),
C6H5.N:N.CHg; mw 120.15, N 23.32%; yel oil, Benzeneazonaphthalene and Derivatives

bp - distills at ca 150°; very easily volat on a B enzeneazonaphtbalene( called Phenyl- a-naphthyl

steam bath. Its prepn and other props are given -diimid; l-Benzolazo-naphthalin or B enzol-azo-
in Beil 16,7 -naphthalin in Ger), C6H5 ,N:N.C, ~H7; mw
Benzeneazotrinitromethane or Phenylozotrinitro. 232.27, N 12.06$%, is described in Beil 16,78
methane (B enzeneazonitroiormate) [ called 1‘, 1‘, Mononitrobenzen eazonapbthalene, C)2N.C6H4 ,N: -
l’-Trinitrobenzeneazomethane in CA, Dec FI N.C ,0H7; mw 277.27, N 15.16%. The [ 3-Nitro-
(1947-56),p 227F] , CsH~.N:N.C(N02)3; mw benzene] - azo-a-napbtbalene, isomer is de-
215.15, N 27.45%; yel powd, mp- expl when dry scribed in Beil 16,78
Dinitrobenzeneazonaph tbalene,
with great violence at 70-5°; cannot be c~std
(02 N)2C6H9 .N:N.CI OH,; mw 322.27, N 17.39%.
from org SOIVS because of decompn. It was prepd
Two isomers are described in Beil 16,78 & [80]
by Quilico(Ref 2) (in the course of his study of Trinitroazonaphthalene,
the reaction betw acetylene and fuming HN03) C ,0 H7.N:N.C6H2(NOZ)3; mw 367.27, N 19.07%.
by treating an aq Amm nitroformate soln with” Two isomers are described in the literature: [2,4,6
benzene diazoniumchloride in the presence of -’.frinitrobenzene] -azo-a-napbtbalene, Red-yel ndls
Na acetate. The subject compd dec rapidly at (from glac ACOH, mp 226° (dec); readily sol in
RT or when heated in an inert SOIV. It expl with glac AcOH; diffc sol in benz or SIC; and [2,4,6
great violence by percussion. Also see Val 1, p -Trinitrobenzene] -azo- @-naphtbalene, dull-red
A67-R ndls(from glac ACOH), mp ca 205 °(dec). The
Its decompn reactions by free radicals have prepn of these isomers is given in Beil 16,78
been studied(Ref 3) & 80 as reported by C. Willgerodt & F .Schulz,
Refs: l)Beil- not found 2)A.Quilico,Gaz~ 62, JPraktChem 43,181-2(1891)& JCS 601,572
503-18 & 912-27(1932) & CA 26,5954-5(1932)& (1891). Their expl props were not detd
27,1348( 1933) 3)G.A.Razuvaev & E .I.Fedotova,
ZhObshchKhim 21,1118-22 & 1219-23(English Benzeneazonaphthol and Derivatives
translation)( 1951) & CA 46,5006-7 & 7534(1952) Benzeneazonaphthol, C6H5.N:N.CloH~.0~;
P.Nitrobenzeneazotrinitromethane, p-02N.CeHa .N:- mw 248.27, N 11.28%. Three isomers are de-
N. C(N02)3; mw 300.15, N 28.00%; orn-yel powd, scribed in Beil 16,151,154,16~( 248,251,254) &
mp- expl with less violence than the compd above. [67.70]
It was prepd by diazotizing Amm formate with Mononitrobenzeneazonaphthol,
02 N. C~H4.N:N.C10H6.0H, mw 293.27, N 14.33%.
P-02N.C6H4N2C1 in the presence of Na acetate
Eight isomers are described in Beil 16,151,155
AISO see Acetylene-Nitric Acid Reaction
165,(248,251,255) & [ 67,68,70] Dinitrobenzene-
Studies, Vol 1, A67-R
azonapbtbol. (02 N)2C6H9 .N:N. C10H5.0H, mw
 I

B 54

338.27. N 16.56%. TWO isomers are described in Benzenediammonium Hydroxide. This compd, of
Beil ]6,(252,255) & [71] which the Azido deriv is listed in Vol l,p A630
-L, should read Benzenediazonium Hydroxide.
See under Benzene Diazo- and Diazonium
Trinitrobenzeneazonaphthol, (02N)~C6H2.N:- Derivatives
N.C ,0H6 .OH; mw 383.27, N 18.27%. Three iso-
mers are described in the literature: [2,4, 6- Tri-
Benzenediazoanilide. Same as Diphenyltriazene
nitrobenzene] - <I azo 2>. (I ).napbtbol, brn ndls
(from glac ACOH); mp 230°(dec); sol in aq NaOH,
giving a violet color; sol in H2S04, giving an BENZENE DIAZO.AND DIAZONIUM
olive-grn color(Ref 1) DERIVATIVES
[ 2,4,6 -Trinitrobenzene] -<l azo 4>-(1)-napbtbol,
The aromatic diazo compds contain the char-
yel-brn or dk-red, blue shiny crysts(from glac
acteristic group(-N:N-) which has replaced one
ACOH); mp 249°; SOI in cold dil NaOH, giving
H atom of a cyclic system. The grotlp shows both
a blue-viol color; sol in H2S04, giving a purple
mula [Ar.N2] ‘X-are formed with acids and of the
-red color. Forms blue, golden shiny Na & K
formula [ Ar.N2 .O-] Na+with bases. The diazo com-
salts(Ref 2) and
[ 2,4, 6- Trinitrobenzene] -<1 azo 1 >-(2)-naphtbol, pds are very reactive and are usually expl. They
grn-blue crysts(from glac AcOH) or red-brn cubes are formed when nitrous acid acts at low temp on
(from MNB), mp 290-2°(dec); sol in coned H2S04, salts of aromatic amines
giving a blue-viol color; mod sol in benz; diffc Diazo compds were discovered by Griess in
SOI in boiling alc(Ref 3). The prepn of these iso- 1858. The procedure by which these compds are
mers is given in the Refs. These compds are formed is called “diazotization”. The diazo com-
probably mild expls pds are not isolated from their solns as such but
Re/.s: l)Beil 16, [67] 2)Beil 16, [68] 3)Beil in the form of salts or bases, called ‘diazonium
16, [71] compounds”. Lower members of the aromatic
diazo compds are very violent expls and for this
Benzeneazonitronaphthol and Derivatives reason only small quants should be prepd at a
time. As the amt of carbon in a compd is in-
B enzeneazonitronaphtbol, C6H5.N:N.C, ~H5(N02).
creased the expl props become weaker. For ex-
OH; mw 293.27, N 14.33%. Three isomers are de-
ample, diazo compds of toluene, xylene, naphthal-
scribed in Beil 16,153,161 & (267)
ene, etc are less violent expls and less sensitive
Mononitrobenzeneazorzitromaphtbo~, 02 N.C6H4 .N:
than the corresponding compds of benzene
N.C1 ~H5<N02).0H; mw 338.27, N 16.56%. Four
Refs: l)Beil 16,427,(352) & [268] 2)P.Giiess,
isomers are described in Beil 16,154,161,(268) &
Ann 106,123(1858); 1 i3,201(1860); 121,257(1862);
[67]
137,39(1866) 3)P.Griess,PrRoySoc 9,594(1858);
Dinitrobenzeneazonitronaphthol, (02N)2C6H3.N:-
11,263(1861); 12,418(1862); 13,375(1864) 4)A.
N.C10H5(N02).0H; mw 383.27, N 18.27%. Only
Eibner, “Zur Geschichte der aromatischen Diazo
the [ 2,4-Dinitrobenzene] -<1 azo 1>- [ 4-nitro-(2)
Verbindungen”, Mhchen-Berlin(1903) 5)J.C.
-napbtbol] , dk-red, greenish shiny Ifts(from ani-
Cain, “Chemistry and Technology of Diazo Com-
sole), mp 205-250°; sol in coned H.#04 giving
pounds” ,London( 1920) 6)A.Hantzsch & G.Red-
an indigo-blue soln, is described in Bei[ 16, delien, “Die Diazoverbindungen”, Berlin(1921)
(268). This compd is probably a mild expl 7)N.V.Sidgwick, “The Organic Chemistry of Nitro-
Trinitroberzzeneazorzitronupbtbol, (02N)3C6H2.N:- gen”,Oxford,Clarendon Press(1942) 8) E. F. Deger-
N.C1 OH5(N02).0H - not found in Beil or in CA ing, “An Outline of Organic Nitrogen Compounds”,
thru 1956 University Lithoprinters,Ypsilanti, Michigan(1945),
334-363 (contains 330 references) 9)W. J .Hickin-
Benzeneazonitroformate. See Benzeneazotrinitro- bottom, Reactions of Organic Compounds, Long-
methane mans, Green & Co, London(1948),259 10)K.H.
Saunders, “The Aromatic Diazo-Compounds and
Benzene Carbonal. See Benzaldehyde Their Technical Applications”, E. Arnold & Co,
London(1949) ll)P.Karrer, “Organic Chemistry”,
Benzene Carbon Amide. See Benzamide
Elsevier,Amsrerdam( 1950),293,522 & 836(Ali-
 B 55

phatic Diazo compounds) and pp 476 & 818(A- high temp; and other metal salts(Ref 2)
romatic Diazo Compounds) 12) L. F.~ieser & Mary Re/s: l)Beil 16,433,(352) & [268] 2) R. Ciusa
Fieser, “Organic Chemistry”, Heath & Co, Boston et al, Gazz85,1501( 1955)&CA 50,10669(1956)
(19s0),644,649-661 13)R.C.Fuson, ”Advanced 4.Azidobenzenediazonium Hydroxide, N3 .C6H4-
Organic Chemistry”, J. Wiley-& Sons,NY(1950), N2.0H; exists only in the form of its salts, some
520,548-572 of which are expl. They are described in Beil
Benzene Diazonium Chloride(Diazobenzene Chlor- 16,493
ide), C6H5.N2. C1; mw 140.57, N 19.94%, OB to Mononitrobenzenediazonium Hydroxide, 02N-
C02 -165% COI ndls(from alc by pptn with eth), C6H4.N2.0H; mw 167.12, N 25.15%. The 2-Nitro,
readily sol in w or cold AcOH; sol in abs alc 3-Nitro and 4-Nitro isomers in both the normal
or acet; insol in benz, chlf, “eth or Iigroin. Can and iso forms are described in the literature. Fol-
be prepd by reacting equim amts of aniline and lowing are some of their expl salts: 2-Nitroben-
sodium nitrite in the presence of an excess of a zerzediazonium Nitrate, 02 N.C6H4 .Nz .0.N02, wh
mineral acid at low temp(O-5°). other mehods of plates, expl on heating; 2-Nitro-benzenediazon-
prepn and props are given in the Refs. Its tox- ium salt of 2-nitrobenzpnesul finic Acid, 02N -
icity is unknown(Ref 4) C6H4.N2.0.S0.C6 H4.N02, yel trysts expl vio-
This compd is hygr but the dry salt is sen- lently ca 100°; 2-Nitrobenzenediazonium Chlor-
sitive and expl on impact. It forms many expl ide+ Lead Chloride, 2(02 N.CeH4 .N2 .Cl)+PbC14;
salts and addn compds, such as: Chloride + yel trysts, expl ca 120-22°; 3-Nitrobenzenedi-
Bismuth Chloride, CGH5.N2.Cl+BiC13, CO1 Ifts, azorzium Nitrate, 02 N. C6H4. N2.0.N02, wh ndls,
mp 85-7 °(dec), expl ca 120°; Cblorodibromide, expl violently on heating; 3-Nitrobenzerzediazon-
C6H~.N2.ClBr2, red-yel tryst pdr, mp 61°, ium Chloride+L ead Chloride, 2(02 N.C6H4 .N2 .Cl)
very unstable; Dicldoroiodide, CeH5 .N2 .C121, +PbC14, wh Ifts, expl ca 160-3°; 4-Nitrobenzene-
yel ndls or Ifts(from ale), mp 86-7 °(dec); diazorrium Chloride, 02 N. C6H4.N2.CI, COI ndls,
Cbloride+Lead Chloride, 2(C~H5 .N2 .Cl)+ PbC14, dec with expln ca 85°; 4-Nitrobenzenediazonium
straw-yel lfts, mp- unstable, expl ca 80-1°; Bromide, 02 N.C6H4 .N2 .Br, citron-yel Ifts, very
Chloride + Mercuric Chloride, C6H5 .N2 .Cl+HgC12, expl; 4-Nitrobenzenediazonium Azide, 02 N.CeH~
wh ndls, mp. dec ca 122°; Cbloride+Mercuric Cy- Nz.lY3, wh ppt, expl in dry state; and Picrate, yel
anide, C6H5.N2. Cl+2Hg(CN)2+ H20, ndls, mp- ndls, dec ca 109-10° with frothing and turning brn;
expl ca 107°; Chloride+ Chloroplatinate,2 (C6H~. 4-Nitrobenzenediazonium salt 01 NapbtbaZene Sul-
~2.Cl) + PtC14, yel prisms, mp- expl on heating; fonic Acid, 02 N. C6H4.N2.03S.C10H7, solid, ex-
and Benzenediazonium Cbloride+Zinc Chloride, pl~on heating; 4-Nitrobenzenediazonium Chloride
C6H5.N2.Cl+ZnC12; the pptd compd, dried by + Lead Chloride, 02 N.C~H4 .N2.Cl+PbC14, yel
washing with acet, expl on storage in a vacdesic Ifts, dec on long storage, expl ca 132-3 °(Ref 1)
after 15 hrs at RT(Ref 3) Ciusa & Oreste(Ref 2) prepd numerous metal-
Re/s: l)Beil 16,431,(352) & [ 268] 2)Karrer (1950), lic salts of 2-Nitrobenzene-isodiazonium Hydrox-
ide and found the Ni, Cu, F e~Al,Cd,Co & uranyl
pp 461-2 3)G.D.Muir, Chem&Ind (Paris) 1956,58
salts defgr when heated, while the Co & Cd salts
-9 & CA 50,9021-2(1956) 4)Sax(1957),545-6
expl when treated with coned sulfuric acid
Refs: l)Beil 16,480 #82 & 483,(356,357 & 358)
Benzenediazonium Hydroxide and Derivatives
& [ 274 & 275] 2)R.Ciusa & D. Oreste,Gazz 78,
Benzenediazonium Hydroxide(Diazobenzene Hyd.
57-60(1948) & CA 42,6761(1948)
rate), CeH~.N2.0H; mw 122.12, N 22.94%. This 2,4-Dinitrobenzene-l -diazonium Hydroxide,
compd exists as the normal or syn- and the iso or (02 N)2C6H3.N2.0H; mw 212.12, N 26.42%. Many
anti-diazonium hydroxide. Both forms exist only of its salts and other derivs have been prepd but
in solns because they decomp easily into phenol their expl props were not reported
and nitrogen. They readily form salts, many of Refi Beil 16,(358)& [ 278]
which are expl: Silver- benzene-norm aldiazotate, 2,4,6.Trinitrobenzene.l. diazonium Hydroxide,
AgC6H5N20, gray-wh trysts, explg violently on (02 N)3C6H2.NZ.0H; mw 257.12, N 27.24%. Some
heating to ca 118°; Potassium- benzene-isodi- salts were prepd but their expl props were not
azotate, KC6H~N20, wh Ifts, explg on heating reported
above 130°; Silver- benzene- isodiazotate, AgC6- Refi Beil 16, [278]
H5N20, wh trysts, explg violently on heating to Benzene.bis.diazonium Hydroxide, C6H4 [N(iN)-.
 I

B 56

OH] ~; mw 166.14, N 33.73%. Salts of both the 2,4.Dinitrobenzenediazonium Nitrate(2,4-Dinitro-

1,3- and 1,4-isomers have been prepd, some of diazobenzene Nitrate), (02 N)2C~H3.N(lN).0 .N02;
which are expl. Salts of B erzzene-bis-(1, 3-di- mw 257.12, N 27.24%; lustrous yel plates, mp-
azonium hydroxide): Chloride, C6H4 (N2 .C1)2 ,yel expl violently when heated. Was prepd by treating
trysts, very expl; -$ul/ate, C5H4 (N2 .0. S03H)2 2,4-dinitroaniline with dil nitric acid and N oxides
ndls, expl on heating; Chloroawwte, C= H4(N2’C1)2. under cooling(Ref 2) or by treating 2,4-dinitroani-
+2 AuC13 , y el ndls, expl; Chloroplatinate, C6 Ha - Iine with K pyrosulfate in highly coned nitric acid
(N2 .C1)2 +PtC14, yel Ifts, expl violently on heat- under cooling(Ref 3)
ing(Ref 1). Salts of Benzene- bis-(1,4-diazonium Refs: l)Beil 16,493 2)T.Curtius & G. M. Dedichen,
bydroxide)Chloride, yel ndlsj very unstable expl JPtChem 50,268(1894)& JCS 68 1,30(1895) 3)0.
compd; Sulfate, ndls, expl on heating; Percblor- N.Witt,Ber 42,2957(1908)
ate, lt-yel ndls, extremely expl; Chloroplatinate,
yel tryst ppt, expl and Boro/luoride, brn-yel Benzenediazonium Oxa!ate Diazobenzene Oxalatel
tryst, dec ca 186 °(Ref 2) C6H5.N2.0C0.COOH; mw 194.14, N 14.43%; COI
Refl l)Beil 16,514 & [285] 2)Beil 16,515,(326) ndls(from MeOH by pptn with eth), mp- expl on
& [285] heating; sol in AcOH or MeOH; S1 sol in ale; insol
Benzenediazonium Nitrate (Diazobenzene Nitrate) in eth. Cart be prepd, according to Knoevenagel
(caHed Aniline Fulminate in Fr), C6H5 .NZ.O - (Ref 2), by treating aniline oxalate with amyl ni-
N02; mw 167.12, N 25.15%; CO1 ndls(from alc by trate in abs alc at ca OO. This compd expl violent-
pptn with eth), mp- expl ca 90°, d 1.37, Q; 78.4 ly on impact
kcal/mol, Q: 114.8kcal/mol, Q~47.4 kal/mole; Re/s: l)Beil 16,432 2) E. Knoevenagel,Ber 28,
v sol in w; sl sol in ale; nearly insol in eth, benz 2059(1895)
or chlf. Its toxicity is unknown but its expln haz-
ard is severe when slightly shocked or exposed Benzendiazonium Perchlorate and Derivatives
to heat(Ref 10). Berthelot & Vieille(Ref 2) prepd Benzenediazonium Perchlorate Diazobenzene Per-
the compd by passing nitrous gas into a cooled chlorate), C6H5.N2.0C103; mw 204.57, N 13.69%;
aq soln of aniline nitrate, dilutg with an equal
COI ndIs, mp- expI; sol in w. It can be prepd by
vol of alc and pptg by the addn of excess ether.
mixing a 10% aq soln of benzenediazonium
Other methods of prepn are given in Refs 1,8 & 9
chloride with a diI aq soin of perchloric acid !
Benzenediazonium nitrate detonates easily by
(Refs 2 & 3) or by other methods(Refs 1,4& 5).
impact or friction. Some of its expl and other props
are given by Wohler & Matter(Ref 4): Covolume This compd, when dry, is a violent expl, extreme-
pf lg, 0.815 vs 0.315 for MF; Explosion Temper- ly sensitive to the slightest shock. ExpIn occurs
ature, 90° VS 190° for MF; Heat of Combustion, sometimes with it in a moist condition and for
678kcal/kg vs 403 kcal/kg for MF; Initiating A c- this reason it has not found practicaI application,
tiorz, does not initiate HE’s such as PA; Lead However, Herz(Ref 4) patented its use in detona-
Plate Test, lg incompletely punctured a 3mm lead tors
plate; MF under tie same conditions punctured Re/s: l)Beil 16,431 2)D.Vorl~nder,Ber 39,2714
the plate completely; Trauzl Test, expansion ( 1906) 3)K.A.Hoffmann & A. Arnoldi,Ber 39,3147
for a 2.Og sampIe at d 1.45 was 43.lml vs 25.6 ( 1906) 4)E.Herz,BritP 27198(1912) & CA 8,1672
for MF at d 3.37 (1914) 5)A.Stettbacher,SS 11,147(1916)
Uses: This compd has been proposed, as a subst m.Nitrobenzenediazonium Perchlorate [ ( l-Diazo-3
for MF in detonators and for use in some ignition -nitrobenzene)-P erchlorate] (called Diazo-m-nitr-
compns. Mixed with LA, it was patented for use in anilinperchlorat or Blitzpulver in Ger), 02 N. C6H4.
detong revets(Ref 7) .N2.0C103; mw 249.57, N 16.84%; trysts, mp-ex-
Re/s: Beil 16,432 & [ 352] 2)M.Berthelot & P. pl ca 154°. This compd was first prepd by Herz
Vieille,MP 1,99-108(1882-3) 3)Daniel(1902),28 & (Ref 2) from m-nitroaniline, perchloric acid and
462 4)L.Wo%ler & O. Matter,SS 2,204,245-7 & 266 Na nitrite. Davis(Ref 4) gives a detailed method
.9(19o7) 5)Matshall 2(1917),512 6)W.Arthur, IEC of prepn. Also see Stettbacher(Ref 5)
9,395(1917) 7)Dynamit-AG,BritP 528299(1940) & It expl on heating, impact or by friction. It was
CA 35,7716(1941) 8)Davis(1943),442 9) F. H. West- patented as a primary or initiating expl to replace
heimer et al, JACS 69,773(1947)& CA 41,4783 MF and reported to have been used in Germany as
(1947) 10~ax( 1957),546 a primary chge in compd detonators, with nitro-

1 —.
 B 57

mannite(or other HE) as a base chge. According N 15.15%. Three isomers are known. They are
to Colver(Ref 3), a detonator contg 0.015g nitro- all expl and can be prepd by diazotizing the cor-
benzenediazonium perchlorate will expl PA, responding aniline sulfonic acid: Ortho or 2-Di-
while 0.1 to 0.3g will completely deton an AN azo-, COI tryst solid, expl weakly on heating; S1
expl sol in w; decomp in hot w or hot ale; Meta or 3
Refs: l)Beil - not found 2)E .Herz,GerP 258679 -Diazo-, CO1 pris~s(from w), expl even by touch-
(1911) & CA 7,2687(1913); BritP 27198(1912)& ing and on heating; decomp in w at 60° or in hot
CA 8,1672(1914) and FrP 450897(1912) & JSCI ale; and Para or 4-Diazo-, CO1 ndls(from w); expl
in dry state by heating(fl p 150°, Ref 2), on im-
32,627(1913) 3)Colver(1918),738 4)Davis(1943),
pact or friction; sol in hot w or dil alkalies; de-
442-3 5jStettbacher(1948),99
comp in hot alc
Benzenediazonium Picrate (Diazobenzene Picrate), Re/s: l)Beil 16,557,559,561 & (369) 2)Dynamit
-AG,BritP 528299(1940) & CA 35,7716(1941)
C6HS.N2.0.C6H2(N02 )3; mw 333.22, N 21.02%;
3)Sax(1957),546
yel ctysts, mp- expl at 85°; insol in W, eth or
benz. Can be prepd by mixing aq solns of benzene. 2.Azido.4.diazobenzenesulfonic Acid(called 2
diazonium nitrate and sodium picrate. Other meth- -Azido-4-diazo-benzol-sulfons~ure-( 1) in Ger),
ods of prepn and props are described by Huisgen
NZ.C6H3(N3).02.S, mw 225.20, N 31.06%; orn
& Horeld(Refs 2 & 3) L_’. o--..--l
Re/s: l)Beil 16,432 & (353) 2) R. Huisgen & G. -red trysts, mp- very expl. Can be prepd by pas-
Horeld,Ann 562,137(1949) & CA 46,8622(1952) sing N oxides through an alc suspension of 2
3)R.Huisgen,Ann 573,163(1951) & CA 46,8622
-hydrazino-4-amino- l-benzene sulfonic acid
(1952)
Re/s: l)Beil 16,565 2)H.Limpricht,Ber 21,
34 14( 1888)
Benzenediazonium Sulfate (Diazobenzene Sulfate),
p.Nitrobenzenediazonium.2,I.naphtholsulfonate,
C6H5.N2.0.S03H; mw 202.18, N 13.86%; wh hygr
02 N.C6H4.N2.0.C ,0 H6S03H; mw 373,56, N
prisms(from aq alc by pptn with eth), mp- expl ca
11.31%; lt orn crysts(from w at 400), mp- dec
100°; v sol in w; S1 sol in dil ale; insol in eth.
90-1000; expl on rapid heating. Can be prepd
Can be prepd by treating, in the cold, aniline sul-
by reacting p-nitrobenzenediazonium chloridq
fate in a mixt of glac AcOH with the calcd amt of
with 2, l-naphtholsulfonic acid in HCI. Warming
sulfuric acid and a sl excess of amyl nitrite. This
the aq soln at 60° gives the diazo~xy compd,
compd expl from heat or shock
while at 70° para red dye is formed. The di-
Re/s: l)Beil 16,431-2 2)P.Griess,Ann 137,48
azodxy compd, 02 N. C6H4.N2 .O.C, OHG.(S09-
(1866) & JCS 20,41-3(1867) 3)E.Knoevenaie4
Na)-(.1,2), pale orn-brn, very unstable, is best
Ber 23,2996(1890)
prepd from the above reactants in NaHCO~,pptd
Benzenediazonium Sulfocyanate (Diazobenzene by sodium chloride
Sulfocyanate or Diazobenzene Thiocyanate), Re/s: l)Beil- not found 2)H.T.Bucherer & C.
Tama,JPraktChem 127,41(1930) & CA 24,4280
C6H5.N2.SCN; mw 163.19, N 25.75%; yel solid,
(1930)
mp- expl ~n heating or impact. Can be prepd by
mixing. an ice cold soht of benzenediazonium
Benzenediazonium Tetrachloroiodide(Diazobenz-
chloride in abs alc with the calcd amt of K sul-
ene Tetrachloroiodide), C6H5.N2.1C14; mw373.87,
focyante. This is a very powerful, sensitive
and unstable expl N 7.5WO; bright yel prisms(from dil soln of io-
dine trichloride in coned HC1), mp 88° (dec),
Re~s: l)Beil 16,432 2)A.Hantzsch & B.Hirsch, sometimes explg. Was prepd by treating benzene-
Ber 29,948(1896) diazonium chloride with a cooled soln of tetra-
chloroiodic acid(HIC14). This compd is stable and
Benzenediazonium (or Diazobenzene) Sulfonic can be kept indefinitely if sealed in glass or kept
Acid and Derivatives in a desiccator filled with chlorine
Benzenediazonium Sulfonic Acid (Diazobenzene R e/s: l)Beil 16, [268] 2) F. D. Chattaway et al,
Sulfonic Acid), N2.C6H4.02.S; mw 184.17, JCS 125 11,1980-2(1924)
Lo—l
 1

B 58

Benzenediazonium Tribromide(Diazobenzene Tri- Re/s: l)Beil 16,520 2)Beil 27,567

bromide), C6H5 .N2. Br3; mw 264.95, N 10.5 S%; Mononitrobenzenediazooxide, C6H9N303, mw
orn-red ndls, mp 63.5° (dec), expl we~ly on heat- 165.11, N 25.45%. The following isomers are
ing; diffc sol in cold ale; insol in w or eth. Can reported by Morgan & Porter(Ref 6): 2-Nitroben-
be prepd by treating a benzenediazonium chloride zene-4-diazo- 1-oxide, -.-..– ...0
soln with an aq K bromide soln and by reacting HC=C—$.N02 I ;
bromine in a hydrobromic acid soln with a soln ff/=C-CH
of benzenediazonium nitrate or sulfate. The dry & N
comp is stable but in a humid atm it dec into 2,- yel Ifts(from hot w), mp- exploded with consider-
4,6-tribromophenol. It rapidly dec in the presence able violence at 168°; mod sol in acet or et acet;
of alc S1 sol in methyl or ethyl ales; insol in benz or
Z?e/s: l)Beil 16,431 2)F.D.Chatcaway, JCS 95, chIf. Was prepd by diazotization of 2-nitro-4-am-
865(1909) inophenol with NsN02 in cold dil H9SOa or by
diazotization of 4-chForo-3-nitroanil~ne in mod
Benzenediazonium Salt of Trinitromethane,C6H5 - coned HCI or sulfuric acid, followed by partia’1
N:N.0.NO:C(N02)2; mw 255.15, N 27.45%; yel neutralization(Ref 1); 3-Nitrobenzene-4-diazo-l-
prisms(from acet+eth), mp- expl violently ca 40°; oxide, brn-red ndls(from et acet), mp- expl at 119°;
SOI in acet or hot w; diffc sol in cold w; almost readily sol in warm w to a pale yel soln; mod sol
insol in ale, eth, chlf or benz. Can be prepd by in ale, acet or et acet; diffc sol in benz; insol in
reacting in the cold aq solns of benzenediazon- eth. Was prepd by treating 3-nitro-4-aminophenol
ium acetate and K trinitromethane. This compd with ethyl nitrite in glac AcOH or by treating an
is fairly stable in the pure state, but very un- eth-alc soln of 3-nitro-4-aminopheno1 with nitrous
stable when impure. It expl when heated or on oxide fumes(Ref 2); 4-Nitrobenzene-2 -diazo-l
impact -OXZ‘d e, ~—N=~
Re/s: l)Beil 16,(352-3) 2)G.Ponzio,Gazz 45 H$= C —$
11,21(1915)
HC=C(N02 )–CH; red-brn ndls, mp
-expl ca 118°; easily sol in cold HCI or H2S04;
Benzenediazooxide and Derivatives sol in ale; diffc sol in w or eth. Was first prepd
B enzerzediazo~xide or B enzoxadiazole (called by Griess(Ref 5) by treating an ether soln of 4-ni-
Benzooxdiazol in Ger), tro-2-aminophenol with HN03(Ref 4); .5-Nitrobenz-
ene-2-diazo-l-o.ride, red ndls(from acet or et acet);
9-N ‘N ~ mp- darkened at 95°, became black at 105° and
H$= C—i ‘r H =C—$-~=N; exploded violently at 11 1°; mod sol in hot w or
HC=CH— CH H z =C—CH ale, giving a yel soln; sol in acet or et acet, giv-
ing an orn-red soln; diffc SOI in eth or benz. Was
(in CA called 1,2, 3-Benzoxadiazo!e or Benzene
prepd by treating 5-nitro-2-aminophenol with Na
-2-diazo-l-oxide; in BeiI called Benzo-1,2,3
nitrite in dil HC1 or with ethyl nitrite in glac Ac-
-oxdiazole)
OH(Ref 3)

~o ~ The thermal decompn of these nitrobenzene-

diazo~xides, in a vacuum, has been studied betw
H$=C—$H H$=C—$H
or 50 and 120° by Vaughan & Phillips(Ref 7). Under
HC=C—CH HC=C—CH ;
these conditions, mononitrobenzene-2 -diazo-l-ox-
N—- N +~=N
ides appear to be less stable than the correspond
(called B enzene-4-diazo- l-oxide by Morgan & ing 4-di azo- l-oxides
Porter), mw 120.11, N 23.33%. These compds Re/s: l)Beil 16,(364) & [ 289] (describes this
are cons idered to be derived from diazophenols compd as 2-nitro-4-diazophenol) 2 )Beil 16,(364)
and info available suggests that they have not (describes this compd as 3-nitro-4-diazophenol)
hitherto been isolated. The constitution and 3)Beil 16, (363) (describes this compd as 5-nitro-
structure of the diazo~xides has been the sub- -2-diazophenol) 4)Beil 16,524, (363) & [ 287] (de-
ject for considerable discus sion (Ref 1) and scribes this compd as 4-nitro-2-diazophenol)
they are of great industrial interest due to the ~)P.Griess,Ann 113,212(1860) 6)G.T.Morgan &
expI nature of their derivs, and the azo dyes J. W. Porter,JCS 107 1,651-6(1915)& CA 9,2061-2
and valuable “lakes” which other derivs form (1915) 7)J.Vaughan & L. Phillips,JCS 1947,1560
 B 59

& CA 42,3571(1948) impact Sensitivity - less sensitive than MF & LA

(Ref 9); FI 18% PA(Ref 10); 4-7” vs 2-4” for MF
DINITROBENZENEDIAZOOXIDE or DIAZODI- by PicArsn App with 1 lb wt using 15mg samples
NITROPHENOL (Called Dinitrodiazophenol or (Ref 25); Power by Trauzl Test, 97% PA or 110%
Dinitro-chinon-diazid in Ger),
C6HZN405, mw TNT(Ref 10); Rate of Detonation, 4400m/sec at
210.11, N 26.67%, OB to C02 -61.0%. Two iso- d 0.9, 6600 at d 1.5 and 6900 at d 1.6(Ref 25);
Sensitivity as an Initiator, min amt of DADNPh
mers are described in the literature:
4,6-Dinitrobenzene-2-diazo-l-oxide or 5, 7-Di-
required to initiate 0.5g of the following HE’ S:
nitro-1 ,.2, 3- benzoxadiazole, (4,6-Dinitro-2-diazo- Tetryl 0.075g, HNDPhA 0.075, PA 0.115 and
TNT 0.163. All expls were pressed at 3400psi
phenol or 3 ,5-Dinitro-l,2-benzoquinone- I-diazide),
(Ref 5); Shock Sensitivity - initiated by shock at
commonly known as Diazodinitrophenol (DADNPh
Mach 5.5-6 .3(Ref 22); ~tdility - no 10SS in power
or DDNP) or Dinol
after 5mos wet storage; stable to diffused light
02N.$= f _c.iE~; and to storage at 60°; darkens in direct light (Ref
HC=C(N02)-~H 5); effect of gamma radiation on DADNPh was
yel lfts(from ale), mp 157-8 °(expl violently at studied by Rosenwasser(Ref 23) (See also Heat
higher temps); apparent d 0.27, tryst d at 25° Test,lOOO and Vacuum Stability, 1000); Time Lag
1.65, pressed d 0.86 at 3400psi(239kg/cm2 )(Refs Before initiation by DADNPb is discussed in Ref
9 & 10), pressed d 1.14 at 3000psi(Ref 25). SOl- 20; Vacuum Stability, 100°,7 .6cc/5g/40hrs(Ref
ubilities in g per 100g solvent at 50°: 2.45 in 25); and Volatility - unaffected in 30 months at
ethyl acetate, 2.43 ethanol, 1.25 methanol, 0.73 50°
ethylene dichloride, 0.23 benz, 0.15 toluene & Uses. DADNPh is a HE suitable for use as an
0.11 chlfi 0.08g in ether at 30°(Refs 9 & 25} mod initiating expl. Its props & suitability as an expl
sol in glac AcOH; nearly insol in w, CC14, CS2 have been studied extensively by Clark(Ref 5),
& petr ether. Was first prepd by Griess(Ref 3) by Grant & Tiffany Ref 11) and reviewed by Fiche-
diazotization of 4,6-dinitro-2-aminophenol(pic- roulle & Kova 4he(Ref 16). Rolland(Ref 14) pro-
ramic acid) with Na nitrite in dil hydrochloric or posed a compd detonator with PETN as a base
sulfuric acid. Other methods of prepn are listed chge with a superimposed initiating chge consist-
in Ref 1. Davis(Ref 9) described a lab method. ing of DADNPh 75 and expl org nitrate(nitroman-
Patents for industrial prepns were granted to Han- nite, nitrodulcite or nitrostarch) 25%. Schuricht
cock & Pritchett(Ref 6), Alexander(Ref 7), and (Ref 19) proposed an ammunition priming com-
Babock(Ref 8) position as follows: Complex salt(LSt, basic LSt
Explosive and Other Properties of DADNPh: or lead hypophosphite) 48.5, Tetracene 5.0,
Activation Energy 55kcal/mol(Ref 18); B ekavior DADNPh 7.0, Pb nitrate 19.0, ground glass 19.0,
‘Towards Flame - ignites and burns like NC, even gum arabic 1.0 & Aerogel O. 5%. Tsukii & Kichu-
in quantities of several grams(Ref 9); Brisance, chi(Ref 21) patented an expl compn suitable for
by Sand Test -95 & 99% TNT(Ref 25)& 200%MF riveting and constg of DADNPh 60 & Tetracene
(Ref 10); Brisance, by Lead Block Compression 40% or DADNPh 60, Tetracene 20& RDX(or NGq)
Test - 71% TNT(Ref 10); Burning Rate 2.15cm/sec 20%, with KC103 or KN03 added as an oxidg
at atm, pressure, for sample in the form of com- agent
pressed cylinders(Ref 12); Compatibility - incom-
patible with LA(Ref 10); Dead-pressing - not dead 2,6.Dinitrobenzenea4.diazo.l.oxide or 2,6.Dinitro.
pressed at 130000psi(9139 kg/cmz)(Refs 9 & 10); uf.diazophenol [ calIed 2,6.Dinitro-p-chinon-diazid-
Electrostatic Discharge, Sensitivity to -0.012 ~
-(4) in Ger] ,
joule s(Ref 25); Explosion ‘Temp eruture -165 °(Ref 02N.~=~— $.NO, ;
17); 195° in 5secs(Ref 25); Friction Sensitivity HC=$— CH
. about the same as that of LA and less sensitive +N SN
than MF(Ref 9); Gas Volume, 865 l/kg(Ref 25); flakes(from mp- expl violently
w), ca 190°. Can
Heat of Combustion 2243cal/g(Ref 25); Heat of be prepd by diazotizing 2,6-dinitro-4-aminophenol
Explosion, 172.2kcal/mol(Ref 10); 820cal/g(Ref or its methyl ether by NsN02 in acid solns(Refs
25); Heat Test, 1000, % Loss:2.1O in 1st 48hrs, 2 & 4). The thermal decompn of these dinitrobenz-
2.2o in 2nd 48hrs; no expln in 100hrs(Ref 25); enediazooxides, in a vacuum, has been studied
Hygroscopicity, 0.04% at 30° & 90%RH(Ref 25); betw 50 & 120° by Vaughan & PhiHips(Ref 15).
 B 60

Under these conditions, 4,6-dinitrobenzene-2 -di- 3*[(l.Benzene-4.dimethyiamino).azo].s(l,2,4)

azo-1-oxide appears to be less stable than the Otriazole,&Azido. See under Dimethylaminobenz-
2,6-dinitrobenzene-4-diazo- l-oxide eneazotriazole and R. Stollt & W.Dietrich, JPrakt-
AmzlyticaZ. Schaefer &Becker(Ref 13) developed Chem 139,202( 1934)& CA 28,27 14( 1934)
a new method for detg diazo N in stable diazo
compds. This method consists in treating a sam- Benzenedioxime. This is a misnomer for Benzal-
ple with a large excess of Ti chloride and meas- dehydeoxime
uring the amt of evolved gas. A method for detg
Benzenehexamethanol and Derivatives
nitro N in stable diazo compds, provided the di-
azo N is known, consists of slowly adding a soln Benzenebexarnethanol,
H0.H2C.$= C(CH20H)-~(CH20H)
of the sample in acetic acid, with swirIing, to a
measured vol of Ti chloride H0.H2C.C=C(CH20H)-C( CH20H). This compd,
prepd by Backer(Ref 2) and called Hexahychoxy-
Re/s: l)Beil 16,524 & [287] 2)Beil 16,531
methyl-benzene, is a parent compd of its hexa-
3)P.Griess,Ann 113,205(1860) 4)R.Meldola &
nitrate
F. G. Stephens, JCS 87, 1204-5(1905) 5)L.V.Cl~k,
Re/s l)Beil- not found 2)H. J. Backer,Rec 54,
IEC 25,663-9 (1933)& CA 27,3611(1933) 6)R.S.
834(1935) & CA 30, 1367(1936)
Hancock & L. C. Pritchett,USP 1952591( 1934) &
Benzenehexamethanol Hexanitrate (called Hexa-
CA 28,3426(1934) 7)H.B.Alexander, USP 2103926
nitrate de Hexa-hydroxym6thy l-benz~ne by Backer ),
(1938) & CA 32,1714(1938) 8)L.W.Babock,USP
c12H12N6018; mw 528.14, N 15.91%, OB to C02
2155579(1939) &CA 33,5869(1939) 9)Davis(1943)
-36.3%. Col crysts(from acet), mp 176.4° with de-
443-6 10)Blatt,OSRD 20141940 ll)R.L.Grant& compn; expl on further heating or on impact(R ef
J .E .Tiffany,IEC 37,661-6(1945) & CA 39,3671
3). Its Qc, Qe, power and temp of expln are given.
(1945) 12)A.F.Belyaev &A. E. Belyaeva,Dokl in conf Ref 3. Was prepd by heating benzenehexa-
AkadN52,503-5(1946) &CA 41,4310(1947) 13)W. methanol in abs nitric acid until complete dis sol-
E. Shaefer &W. W. Becker, AnalChem 19,307-10& ution, followed by cooling
CA 41,4062(1947) 14)G.F.Roland,USP 2422043 Refs: l)Beil- not found 2)H.J.Backer,Rec 54,
(1947) &CA41,5725<1947) 15)J.Vaughan &L. 834-5( 1935) & CA 30,1367(1936) 3)ADL Punch
Phillips,JCS 1947,1560-5 &CA42,357U1948) Cards( 1.954) (Conf) (not used as a source of info)
16)H.FicherouHe & A. Kovkche,Mp 31,7-27(1949)
&CA 46,1186-7(1952) 17)H.Henkin &R. McGill,
IEC ‘i4, 1391-5(1952) & CA 46,8857-8(1952) 18)-4. Benzenesulfenamide and Derivatives
Suduki, JIndExplSocJapan 14, 142-63(1953) & CA Benzenesulfenamide (called Benzolsulfensaure-
49,1 1281(1955) 19)A.G.Schuricht, USP 2662818 amid in Ger), C6H5 .S.NH2; seems to exist only in
(1953) & CA 48,3692(1954) 2@H.subJIndEwl- the form of derivs, such as:
SocJapan 15,277-81(1954) & CA 49,11283(1955) Mononitrobenzenesu~/enamides,(02N)CGH4.S.NH2.
21)T.Tsukii & S. Kichuchi,JapP 4443(1954) & CA Its 2-isomer melts at 120-4°, while the 4-isomer
49,10628(1955) 22)W.A.Gey & H. L. Bennet, JChem- meIts at 99-103°
Phys 23, 1979-80(1955)& CA 50,2174(1956) 23)H. Re/s: l)Beil- not found 2)R.A.CoIeman,USP
Rosenwasser,OakRidgeNatlLab(ORNL)Rept 1720 2,404,695(1946) & CA 41,154(1947)
(1955) & CA 50,14229(1956) 24)Sax(1957),547
25)PATR 1740, Rev 1(1958 ),101-5
2,4.Dinitrobenzenesulfenamide, (02N)2C6H3 .S.NH9;
2,3,6.Trinitrobenzene4.diazo.I.oxide or 2,3,6.
.Trinitro.4.diazoaphenol, C6H07N5; mw 255.11, mw 215.24, N 19.50%. Yel crysts(from ethanol), -
N 27.45%; ocher CO1 prisms(from glac AcOH), mp 119.0-205°. Can be prepd by cleavage of 4-
mp- expl violently; decompd by most s OIVS, and -benzylthio-l,3 -dinitrobenzene with chlorine. Its
tends to retain those which do not react with it expl props were not detd
chemically; decompd by alkalies or carbonates. Re/s: l)Beil- not found 2)R.H.Baker et al,JACS
Was prepd by Meldola & Hay(Ref 2) by diazotiza- 68,2639( 1946) & CA 41,2058(1947) 3)N.V.Khromov
tion of 2 ,3,6-trinitro-4 -aminophenol w ith N SN02 -Borisov & M. B. Kolesova,ZhObshchKhim 25,36 I
in acid soln. Because of its high sensitivity, the -5 & 380(1955)& CA ~,2466(1956)
props of this compd were not detd
Re!s: l)Beil 16,531 2)R.Meldola & J. G.Hay, Benzenesulfenic Acid and Derivatives
JCS 95, 1383-4(1909) B enzenesulfenic Acid or PbenylsuI/obydroxide
 B61

(Called Benzolsulfens~ure in Ger), C6H5.SOH; ard in the prepn and use of 2 ,4-dinitrobenzene-
seems to exist only in the fo~m of its derivs, such sulfenyl chloride) 5)N.Khsrash et al, JACS 77,
as: 931-4(1955) & CA 50,1651 -2(1956) (Hydrolysis of
Benzenesulfenyl Chloride or Pbenylsulfocbltwide. 2,4-dinitrobenzene sulfenylchloride)
(Benzolsulfens~ure-chlorid in Ger), C6H5.SCL
Red Iiq which smokes in the air; bp 73-5° at 9mm; Benzenesulfenylchloride. See above under Benz-
dec when distilled under atm pressure. Its prepn enesulfenic Acid and Derivatives
& props are described in Refs 1,2 & 3. It was re-
Benzenesulfinic Acid and Derivatives
ported (Ref 4) that a glass container with behz-
enesulfenylchloride exploded at Shell Houston B enzenesulfinic Acid(called Benzolsulfins&ue
Research Laboratory after standing undisturbed in Ger), C6H5.S02H; mw 142.18, trysts, mp 83-4°,
for several months is described in Ref 1
Refs: l)Beil 6, [ 295] 2)H.Lecher & F.Hol- Its mononitrocornpounds (2-,3- and 4-isomers)
schneider,Ber 57,757(1924) 3)N.Kharash et al, ruid their salts are described in Ref 2
ChemRevs 39,279(1946) 4)Anon,C&EN 35,N0 47, Davies et al(Ref 3) claimed to have prepd 2;4
p 57(1957) .dinitmbenzenesu~finic acid, (02N)2C6H3.S02%
Mononitrobenzenesulfenylchlorides, 02N.CG,H4.SC1. wh tufts, mp 196°, by he sting 2 ,4-dinitrobenzene-
The following isomers are described in the litera- sulfonylhydrazide with aq hydrazine and dil HCI
ture: 2-Nitrobenzenesul fenylcblotide. Yel ndls and pptg the product by addn of coned HC1. 13rad-
(from benz); mp 75°, expl on further heating, E as- bury & Smith(Ref 4) attempted the same method
ily sol in benz, AcOH & chlfi diffc sol in eth,CC14 of prepn and obtd the sulfonyl hydrazide, C6H6-
& petr eth. Can be prepd by chlorination of 2,2’ N406S which, when crystal from dioxane-water at
-dinitrodiphenyl-disulfide(Refs 1,3,6,7 & 8). 0°, decompd violently at 113°. On warming the
The anhydride of the disulfide, called o .o’-Dinitro- sulfonylhydrazide with HCI at 80 0, filtering rhe
phenyl-schwefeloxyd by Zincke, 02N.C6H4.S.0.- in sol matter and acidifying with coned HC1, oct a-
S.C6Ha .N02, expl at temps higher than its mp 92 hedral ctysts of the hydtazine dichloride(mp 197°)
-3 °(Refs 1 & 2); 3-Nitrobenzenes~~fenyzcbl~~.de were pptd
was prepd by chlorination of 3,3‘-dinitrodiphenyl- No description of higher nitrocompds cou”.d be
disulfide; no props are given(Ref 5); and 4-Nitro- found in the literature (See also Benzenesulfenic
benzenesulfenylchloride, yel scale s(from hexane), and Benzenesulfonic Acids and Derivatives)
mp ’52°; was prepd by chlorination of 4,4’-dinitto- Refs: l)Beil 11,2-6,(3) & [3-4] 2)Beil 11,8,(4)
diphenyldisulfide( Refs 2,4 & 8). The anbyd~ide of & [51 3)W’.D=+S et =4JCS 1931,626 & CA 25>
the disulfide, called p.p’-Dinitrophenyl-schwefel- 2702(1931) 4)H.Bradbury & F. J. Smith,JCS 1952,
oxyd by Zincke, yel lfts(from benzene), dec ca 2943 & CA 47, 1082( 1953)
160° and expl mildly(Refs 2 & 4)
Refs: l)Beil 6,(157) & [308] 2)Beil 6,(160) Benzenesulfonic Acid ond Derivatives
3)T.Zincke & F. Farr,Ann 391,63 & 67(1912) 4)T. B enzenesulfonic Acid (called Benzolsulfons~ure
Zincke & S. Lenhardt,Ann 400,9-12(1913) 5)N.E. in Ger)$ CeH5.S03H; mw 158. 18; solid, when an-
FOSS et al,JACS 60,2729(1938) 6)J .H.Billman & hyd, mp 55-6°. It forms numerous salts and other
E .O’Mahony,JACS 61,2340- 1(1939) 7PrgSynth- derivs, some of which are expl. The prepn and
COIIVO1 2(1943),455 8)N.Khatash et al, ChemRevs props are given in Beil 11,26-9,( 18-20)& [ 9-1 I] .
39,281(1946) This compd can cause serious local toxicity to
2,4-DinitrobenzenesulfenylchIoride, (02N)ZC6H3= skin and mucous membranes, as reported by Sax
SC1; yel trysts, mp 94-6°. Can be prepd by reac- (1957),P 347
tion of chlorine with a suspension of 2 ,4-dinitro- Benzenesulfonyl Azide (called Benzolsulfons~ure-
phenyldisulfide in MNB(Refs 2 & 3). It is a danger azid in Ger), C6Hs.S02.Na; mw 183.19, N22.94%;
ous expl and heating it above 90-100° should be yel oil, mp expl on heating; easily sol in ale, eth
avoided(Ref 4) or chlf. Can be prepd from benzenesulfonyl hycira-
Refs: l)Beil- not found 2)J.H.Bilman et al,JACS zide, Na nitrite and AcOH(Refs 1 & 2) or by weat-
63,1920-1(1914) 3)N.Kh-ash et al,JACS 69>1613 ing benzene sulfonyl chloride with Na azide(Ref 3 )
-14(1947) & CA 41,6217(1947) 4)N.Kh-ash,JACS Refs: l)Beil 11,53 2) T. Curtius et al, JPraktChem
72,3322-3(1950) & CA 44,10673(1950) (Exp~n haz- 53, 174(1898): 106,72( 1923) ad 112,92(1926) 3)T.
 B 62

Curtius &J.Rissom,JPraktChem 12fi,312(1930)& or eth, loses w of crystn at ordinary temp and

CA 24,3228(1930) may be heated to 300° without decompn; when
m.Benzenedisulfonyl Diazide, C6H4(S02N3)2; mw heated on Pt in an open flame, it explodes
256.21, N 32.81%; mp 82°, expl at higher temp. Re/s: l)BeiI I I ,80 2)C. WilIgerodt,JPraktChem
Can be prepd by treating m-benzenedisulfonyl di- 32,117(1885) & JCS 48 11,1232(1885)
chloride with Na azide in alc
Refs: l)Beil- not found 2)T. Curtius & H. Meier, Benzenesulfanic Acid Azoacetylhydrazide( called
JPrakrChem ~25,358(1930) & CA 24,3229(1930) Benzolsulfos~ure-azo-acet-hydrazid; 1- [4-Sulfo
Azidobenzenesulfonic Acid, N3.C6H4.S03H; mw -phenyl] -4-acetyl-tetrazen-( 1); or [ 4-Sulfo-benz-
199.19, N 21.09%. The 2-Azido deriv is not de- oldiazo] - [ @-acetyl-hydrazid] in Ger),H03S.C6-
scribed in Beil but the 4-Nitro-2-azido deriv,
H4.N:N.NH.C0.CH~; mw 258.26, N 21.70%. Its
N9L6H3(N02).S03H, is listed; the Potassium
Sodium salt, NaC~H9N404S+2H20, wh lustrous
salt, KC6H3N405S, lt-brn lfts, of which$expls ca
tryst, produced from diazobenzene sulfonic acid
1300 (Ref l,p 81 & Ref 3,p 3413). The 3-Azido
deriv, deliq ndls, forms a Barium salt, Ba(C6H4- and acetylhydrazide, explodes when heated. In
N303S)2, in the form of ndls which expl ca 1300 w, the Na benzenesulfonate salt gives hydrogen
(Ref l,p 80 & Ref 3,p 3416). The 4-Azido deriv, azide and Na suIf anil ate; NaOH and p-toluene-
deliq ndls, expl on heating; and also forms a diazonium chloride convert it into hydrogen azide
Batium salt, fairly sol in hot w(Ref l,p 80 & [ 37] and Na p-toluenediazoaminobenzenesulfonate
and Refs 2 & 3) Refs: l)Beil 16,(419) 2)0. Dimroth & G.de Mont-
Re/s: l)BeiI 11,80,81 & [37] 2) P. Griess,Ber molIin,Ber 43,2912-3(1910) & CA 5,494(1911)
20,1529(1887) 3)H.Limpricht, Ber 21,3413 & 3416
(1888) 4)E.NoeIting et aI,Ber 26,87 & 91(1893) Benzenesulfonyl Peroxide (called Dibenzolsulfo-
Mononitrobenzenesulfonic Acid, 02N.C~H4.SO~H; nyl-peroxyd in Ger), C6H5.S02.0.0.02 S. C6H5;
mw 203.18, N 6.90~. Three isomers are describ- mw 314.34, 0 30.6%, co] prisms(from ale), mp
ed in the literature: 2- Nitro deriv, v h ygr trysts, expl ca 53-4°; readily SOI in eth or chlf; diffc sol
mp ca 70°; 3-Nitro deriv, delq lfts; and 4-Nitro in ale; insol in w. Can be prepd from benzene-
deriv, hygr trysts, mp 95°. Hymas(Ref 2) obtd a sulfonyl chloride and Na peroxide in ice cold w.
corrosion resistant coating for ferrous surfaces This compd expl also on impact
by treating with phosphoric acid or alkali phos- Re/s: l)Beil 11,34 2)R.Weinland & H. Lewko-
phate soln to which m-nitrobenzene sulfonic acid witz,Ber 36,2702( 1903)
or certain other org nitro compds have been added
Re/s: l)Beil 11,67-8& 71(20-21) and [ 31-33] Benzenesulfonyl Sulfuric Acid Peroxide(called
2)M.Hymas,IJSP 2657156(1953) & CA 48,2557-8 Benzol-sulfonyl sulfomonopersSure in Ger),
(1954) C6H5.S02.0.0.SOsH; mw 254.25, 044. 1%. Its
Dinitrobenzenesulfonic Acid, (0.#)2CGHa.soaH; Potassium Salt, KC6H507S2, sq prisms(from w),
mw 248.22, N 11.35%. The 2,4-Dinitro, It yel deliq dec on storage and expl mildly when heated
prisms of the trihydrate which melt at 108° and Refi l)Beil 11,34 2)R.Willst~tter & E .Hauen-
lose w of crystn at 130°; and 3, 5-Dinitro deriv, stein,Ber 42,1848(1909)
deliq tryst, are described in the literature. Their
expl props were not investigated Benzenesulfony.l.2,5.tolylenediazoimide [ called
Re/: Beil 11,78-9& [36] N-BenzoI-sulfony l-4-diazo-2-methy l-anilin or
2,4,6.Trinitrabenzenesulfonic Acid(called Pikryl- Toluchinon-benzol stdfonylimid-( 1)-diazid-(4) in
sulfonyIs~ure in Ger), (0.#)3C6H2.S03H; mw Ger] , C6H5.S02.N:(CH~ )C6Hs:Nz or
293.17, N 14.33%; ctysts of the trihydrate, mp- C6H5.S02.~\
sinter ca 100° and the anhyd acid melts ca 185°; N C6H~.CH3; mw 273.31, N 15.38%;
N/
SOI in w, alc & eth; diffc sol in chlf; insol in ben~
Iryel ndls; mp dec explosively at 163 0. Was prepd
Can be prepd by heating an alc soln of picryl
by diazotizing 5-amino-2-benzenesul faminotolu-
chloride with an excess of Na sulfite. Its expl
ene with coned HCf, aq Na nitrite and pptg the
props were not investigared. The Sodium salt,
product by treating the filtrate with Na acetate
(02 N)3C6H2.S03Na+HzO; large COI transparent
Re/s: I)Beil 16,608 2)G.T.Morgan & F.M.
trysts, readily sol in w but sparingly sol in alc
Micklethwait,JCS 87,925-6( 1905)
 B 63

Benzenesulfonyl.p.xylylene.2,5.diozoimide (csl- of air; insol in ale, abs eth, chlf, carbon disulfide
Ied N-Benzol-sulfony l-4-diazo-2.5-dimethy l-anilin or ligroin; det violently with warm w, coned sul-
or p-Xylochinon-benzol-sulfonylimid-diazid in furic acid or coned KOH. Even in ice-cold w, the
Ger), CGH5.S02.N:(CH3 )ZC6HZ :Nz or ctyst mass expl at the S1 touch. Can be obtd by
C6H~.S02.~\ introducing a stream of ozone into pure benz at
~ CGH2(CH3)2; mw 287.33, N 14.62%; 5-10°
# This extremely unstable expl developes about
yel ppt; mp-dec explosively at 125-130°. Was 25% more energy than NG and its vel of deton is
prepd by diazotizing 2-amino-5 -benzene-sulfamino much higher than that of ordinary expls, which
-p-xylol gives it exceptionally great disruptive power(Ref
Re/s: l)Beil 16,609 2)G.T.Morgan & F“Mo 3)
Micklethwait,JCS 87,926-7(1905) Refs: l)Beil 5,197 2)C.Harries & V. Weiss,Ber
37,3431(1904) 3)Anon,SciAmMonthly 1,144(1920)
Benzenetetrazole. A misnomer for Pyrazopyrazine 4)Tobolsky & Mesrobian(1954), 180
listed in CA, Subject Index 1907~ 16,p 4130
Benzenyloxyhydroxytetrazotic Acid. See Phenyl-
Benzenethiol ond Derivatives oxyhydroxytetrazotic Acid
B enzenethiol; Pbenylmercaptan or “Tbiopbenol
(Called Sulfhydtylbenzol or Mercaptobenzol in Benzenyloxytetrazotic Acid. See Phenylozytetra-

Ger), C6HS .SH; liq, bp 168.3°, is described in zotic Acid

Beil 6,294, (142) & [284] . Forms numerous salts
Monorzitrobenzenethiol, (02 N).C6H4 .SH. Its 2-is@ Benzenyltetrazotsaure. Old Ger name for 5-phen-
mer is a solid melting at 61°; the 3-isomer is yl-tetrazole
an oil with repulsive odor and the 4-isomer is a
Benzfurazan. See Benzofurazan
solid melting at 77°. They are described in Beil
6,337-9,(154 & 159) and [303-4 & 308-9]
Benzfuroxan. See Benzofuroxan
2,4.Dinitroherzzenethiol, (02N)2C6H3SH; lt-yel
trysts, mp 131-2°. Its prepn and other props are Benzidine and Derivatives
in Beil 6,342,(162) & [ 315]
Benzidine or 4,4’-Diaminobipbenyl (called 4,4’
2,4,6.Trinitrobenzenethiol; Picrylmercaptan or
-Diaminodiphenyl or Benzidin in Ger ), H2N.C6-
2,4,6.Trinitrothiophenol, (02N)3CGH2.SH; mw
H4.CeH4.NH2; mw 184.23, N 15.21%; grayish-yel
245.19, N 17.14!%. Small yel trysts, mp ca 114°
ctysts, wh or SI reddish ctysts or lfts(depending
and expl violently ca 115°. Easily SOI in cold
w or alc but dec when heated; sol in eth,chlf, on SOIV), mp 127.5-128.5°~ bp 402° at 740mm~ d
acet or benz; nearly insol in CS2 or petr eth. Can 1.250 at 20°. Benzidine is of low order of toxici-
be prepd by adding (under cooling) picryl chlor- ty but it is suspected to be a possible cause of
ide to K2S dissolved in 90% ale, aHowing to bladder tumor and when heated to decomp, emits
stand and then acidifying with a mineral acid highly toxic fumes(Ref 9). Its other props & prepn
Its Potassium Salt, KC6N3HZ06S, reddish-bin are given in Refs 1,4,5,6,7 & 8
ndls, expl violently ca 140° or on impact. Its Ag, It forms various salts and addn compds, the
Cu, Na and Pb salts are also known(Refs 1 & 2). following of which are expl(Ref l,P 219& [90]
The Na salt was also prepd by Thomas et al(Ref and Ref 2} Bromate Cl *H ,2N2+ 2HBr03, dec vi-
3) olently on rapid heating; Chlorate, C, ~H, *N2+
Refs: l)Beil 6,344 & [316] 2)C.Willgerodt, 17, 2HC103, dec explosively on rapid heating or when
Ref 353(1884) 3)V.Thomas et al,CR !78,1289 heated in the presence of traces of nitric acid;
( 1924)&CA 18, 1995(1924) Perchlorate, Cl ~H1 ~N2+HC104; grayish solid,
Benzene Triozonide, formerly known as OzO-beTZz. dec ca 100° and the Dipercldorate, dec explo-
ene (called Benzol triozonid in Ger), o sively on rapid heating; PiCrate, C, ~H, *N2-
/CH-&&H + 2( C~H3N307 ), yel-gm trysts, ewl on rapid
mw 222.11, 0 64.8%; amor mass,
extremely unstable expl, dec in 01 heating; Quinonedicbloroimide, 2(C, *H ,zN2)-
~CH-$~ (! H +C6H4N2C12, violet ndls, mp expl ca 121° [ Ref
a vac and on ezposure to a stream
3
 I

B64

l,p (6o) and Ref la] LeF$vre et al(Ref 2) from the hydrolysis prod
Benzidine has been claimed(Ref 3) to be one of the nitration of 2-nitrodiacetylbenzidine
of a number of compds suitabIe as a sensitizer through the sulfate. The expl props of this compd
for AN were not investigated
Re/s: l)Beil 1.3,214,219,(58) & [90] Ia)A. Refs: l)Beil13, [ 109] 2)R. J. W. LeF?vre et al,
Knorr,Ber 43,799(1910); JCS 98 I,324-5(191O) JCS 1927,2332& 2338&CA 22,69(1928)
2)A.E.Kretov,JRussPhy sChemSoc ~,1427(1928) Note: Higher nitro derivatives of benzidine were
& CA 23,2117-8(1929) 3)W.O.Snelling & J.A. not found in Beil or in CA through 1956 but some
WyIer,USP 18276V (1932) & CA 26,601(1932) addnl higher nitro alkylated benzidine derivs
4)M.S.Fishbein,Voy ennayaKhimia(Russia) 1933, which are expl include the following:
No 6,p 3-8; ChemZtr 1934 II, & CA 29, 7077(1935) N,N,.Dinitro.N,N’.dimethyl.3,5,3’,5’,.tetranitro.
5)K.Ino & R. Oda,JSocChemInd( Japan) 46,552-3 benzidine, [ -CGH2(N02)2 .N(N02).CH3] z; lfts
(1943) &CA 42,6343( 1948) 6)USSpec MIL-B-I 1332 (from fuming nitric acid by careful addn of w),
(1951) 7)M.Zisic & V.Premru,KhemZbornik 1951), mp expl above 220°(Refs 1,3 & 4)
139-42 & CA 48,10687(1954) 8)T.Maki & K. N,N’s.Dinitro.N,N’.dipropyl.3,5,3,5’.tetranitro.
Obayashi,JSocChemInd(J span) 55, 108-9(1952) & benzidine, [-C6H2(N02)2.N(N02 ). CH2.CZH5] ~;
CA 48,5836(1954) 9) It yel flts(from coned nitric acid), mp expl ca
Benzidine, Alkylated(NittoSee Vol
Derivatives). 213°(Refs 2 & 5). Many other alkylated nitrobenz-
l,p A 129-L and Note under 2,5,3’- Trinitrobenzi- idine derivs dec on heating
dine Re/s l)Beil 13,237 2)Beil 13, [ 110]
Mononitrobenzidine, H2N.CGH4.C6H3(NC)2 ).NH2; 3)P.van Romburgh,Rec 5,244( 1886)
mw 229.23, N 18.33%. The 2-Nitro and 3-Nitro 4)K.H.Martens,Ber 19,2126(1886) 5)G.van
-derivs are described in Beil 13,235,(67)& [ 107] Romburgh,Rec 41,42( 1922)
Dinitrobenzidine, HZN.C6H3 (N02).C~H3(N02).-
Benzil and Derivatives
NH2, mw 274.23, N 20.43~. The following isomers
Bend; Bibenzoyl; Dibenzoyl; Dipbenylglyoxal
ate described in the literature: 2,2’- Dinitro-, yel
lfts(from ale), mp 214°(Ref 1) & 200-2°(pptd from or Diphenyldiketone, [ called 1.2-(or a.~-)-di-
phenyl-athan or a;a’-Dioxo-dibenzyl in Ger],
acid soIn) (Ref 2); 2,3’-Dinitro-, deep red ndls
(from phenol-ale), mp 236° & 243-4(Ref l] 3,3’ C6H5 .C0.C0.C5~ ; mw 210.22; yel prisms(from
-Dinitro-, crysts(from pyridine+ ale), mp 275° or eth), mp 95°, bp 346-8° (dec), d 1.23 ar 15°;
red ndls(from phenol), mp 281-2°(Ref 1 & 278-9° Q: 1625kcal/mol(w Iiq); very sol in benz or eth;
(Ref 3) sol in ale; v S1 sol in w. The toxicity of benzil
Other props & prepn are given in the Refs is unknown but it is used as an insecticide(Ref
Re/s: l)Beil 13,235-6,(67-8)& [ 108] 2)B.A. 6). Its prepn and other props are given in Ref 1
Porai-Koshits & M. Bentov,ZhObshKhim 14,1019 and in others(Refs 12345
9999 & 7)
-24(1944) & CA 39,4599(1945) 3)E.D.Bergman & R efs: l)Beil 7;747,(392) & [674] 2)A.Zinn,Ann
M. Bentov,JOC 19, 1598(1954)& CA 49,15765 34, 188(1840) 3)R.Adams,0rgSynth 1(1921 ),25-7
(1955) 4)H.Gilman,OrgSynth 6(1926),6-7 5)S.M.McElvain
2,2’.Dinitrobenzidine Perchlorate. Fishbein(Ref et al,J ACS 73,38 10(1951) & CA 46,6627( 1952)
2) treated 2,2L dinitrobenzidine with nitrous acid 5)Sax( 1957),348 7)USSpec MIL-B-565A( 1958)
and reacted the resulting diazoniutn compd with kionorzitrobenzil, C6H5.C0.C0.CGH4 .N02, mw
perchloric acid to obtain an expl compd which he 255.22, N 5.49%. The 2-, 3- and 4-Nitro derivs
called ‘diazo-2,2 ‘-dinitrobenzidine perchlorate o. of benzil are described in Beil 7,765 & [ 683]
This pre.d was claimed to be suitable for use in Dinitrobenzil, C14H~N206, mw 300.22, N 9.33%.
primary and initiating compositions Nine isomers of diaitrobenzil, none of which
Re/s: l)Beil- not found 2)M.S.Fishbein, Voyenna- seems to be expl, are described in Beil 7,766,
yaKhimia(Russia) 1933, No 6,pp 3-8 & CA 29, (396) & [684-6]
7077(1935) Trinitrobenzil, C ,4 H7N~08-not found in Beil
2,5,3’. Trinitrobenzidine, H.#.C6H3 (N02).C6H2-
Tetranitrobenzil, C ,4 H6N40,0, mw 390.22, N
(N02)2.N~; mw 319.23, N 21.94%; dk-red ndls 14.69%, OB to C02 -86. 1%. TWO isomers are
(from phenoI +alc), mp 276°. It was isolated by described in the literatwe: 2,4,2’, 4’-Tetranitro-
 B 65

berzziZ,(OzN)zC6H~ .C0.C0.CGH3(N02)2; pale & E. E. Turner,JCS 1950,1515 & CA 45,1116(1951)

yel trysts, mp 222-3°; S1 sol irt glac AcOH or 3)L.Monti & G. Franchi,Gazz 81,772(1951) & CA
toluene; insol in other ordinary SOIVS. It was 48,3976(1954)
Benzimidazole.diazid.copper Salt, [(N9 )2CuC7-
prepd by Blatt & Rytina(Ref 5) by heating a soln
of 2,4,2’ ,4’-tetranitrostilb ene with strong mixed H6N2] , expl weakly at 183-5°, but not under im-
acid contg nitric acid, sulfuric acid & oleum, and pact
Re/s: l)Beil- not found 2)A.CiruIis & M. Strau-
pouring it onto a large qusnt of ice. When treated
manis,JPraktChem 162,307-28( 1943) & CA 38,
with alk hydrogen peroxide the tetrsnitroberrzil
1970(1944)
formed 2,4-dinitrophenol(Refs 1 & 5) 3,5,3’,/’
Mononitrobenzimi dazol e, ,NH
-Tetranitrobenzil, pale yel prisms(from AcoI-1),
mp 179°; readily sol in hot AcOH, S1 sol in hot
alc or benz. It was prepd by heating at 100-10°
mw 163.13, N 25.76%. The S(OT 6)-flitro(Refs 1&
3,3’-dinitrobenzil with coned sulfuric acid qnd
2) and the 4(07 7} Nitro (Refs 1 & 2) derivs are de-
nitric acid. It is stabI e in hot nitric and acetic scribed in the literature. The Picrate of 4-nitro-
acids. The expl props of this tetranitro com~d
deriv, mp 184-5°, is described in Ref 3
are between those of DNT & TNT(Refs 2,3 & 4) Re/s: l)Beil 23,135 & [ 154] 2)A.Bamberger &
Re/s l)Beil- not found 2)Bei17, [ 686] 3)@.H.
B .Ber16,Ann 273,340( 1893) 3)G.M.van der Want,
Cristie & J.Kenner,JCS 1926,475 & CA 20,1620 Rec 67,48(1948)& CA 42,5020(1948)
(1926) 4)F.D.Chattaway & E.A.Coulson,JCS Dinitrobenzimidazole,
1927)578 & CA 21,1983(1927) 5)A.H.Blatt & / > NH
‘CH;mw
A.W.Rytina,JACS 72,405(1950) & CA M, 1081 (0’N)*c6H<N/
(1951) 208.13, N 26.92%. The 5, 6-Dinitro deriv, mp 186°,
2,4,2’,4’,6’.Pentanitrobenzil, (02N)2C6Ha.C0.- was prepd by Efros(Ref 2) and the 5, 7(OT 4, 6-Di-
C0.CGH2(N02)3; mw 435.22, N 16.09%, OB to nitro den”v, mp 239-40°(dec), was prepd by Bahner
C02 -68.wO; CO1 trysts, turn” orn-brn in the light; et al(Ref 3). Their expl props were not detd
mp 261°(dec). This compd was prepd by nitration Re/s: l)Beil- not found 2)L.S.Efros,ZhObshKhim
of 2,4 ,6-trinitrostilbene or 2,4,6,2’ -tetranitrostil- 22,1008-15(1952) & CA 47,12366(1953) 3)C.T.
bene with mixed nitric and sulfuric acids. Penta- Bahner et al,JACS 74,3689(1952) & CA 48,5183
nitrobenzil is also obtd from 2,4,6,2’ ,4’-peqta- (1953)
nitrostilbene under similar conditions. It does Note: Higher nitro.derivs were not found in Beil
not form addn compds with naphthalene or anthra- or in CA thru 1956
cene but thiophthene yields an impure yel prod,
mp 220.40. The pentanitrobenzil is recovered un- Benzimidazolol. Same as Hydroxybenzimidazole
changed after boiling with hydroxylamine hydro-
chloride or o-phenylenediamine in glac AcOH. Its Benzimidazolone and Derivatives

expl props were not detd Benzimidazolone or o-Ph enylene-urea (called N:

Refs: l)BeiI- not found 2jF.Challenger & P.H. N’-o-Phenylen-harnstoff; 2-Oxy-benzimidazol;
Clapham,JCS 1948,1612-4& CA 43,1733(1949) 2-Oxo-benzimidazolin or Benzimidazolon in Ger),

Benzimidazole and Derivatives

c <W, /co
6 %NH ‘r
‘NNC
c6H<Nfi “
OH mw
;
B enzimidazole; 1,3-B erzzodiazole; o-Pbenylene
.formamidine or Benzoglyoxaline (called N,N’ -Meth- 134.13, N 20.89%. It forms numerous salts, some
enyl-o-phenylendiam in or Benzimid azol in G er), of which are probably expl. Other props & prepn
of benzimidazolone are given in Beil 24,116,
~N<2H o mw 118.13, N 23.72%. It forms (240) & [62]
c6H4>N/ F’ 5,6.Azimino-benzimidazolone. See 5,6-Azimino
3
-benzimidazole, VOI l,p A643-R
numerous salts and other derivs and addn compds,
Mononityobenzimidazolone, C7H5N303; mw 179.13,
some of which are expl. Other props & prepn are
N 23.46%. The 5-Nitro-deriv IS described in Beil
given in Refs 1 & 2. Its picrate, is described in
24,119 & [242] NH
Ref 3
5, 6-DinitrobenzimidazoZone, (02N)2CGH<>C0,
Re/s: llBeil 23,131,(35) & [ 151] 2)A.T.James
NH
 I

B 66

mw 224.13, N 25.00%; orn-yel ndls(from dil sIc), under V-1 and V-2 (Propellants; Used in)
mp above 300°. Other props & prepn are given in
Beil 24, (242) Benzite(Fr). See 1,3 ,5-Trinitrobenzene under
Trinitrobenzimidazolone, C7H~N507, mw 269.13, Benzene
N 26.02%. The 4,5, 6- Trinitro and 5,6, 7- Trirzitro
derivs were prepd by James & Turner(Ref 2) who Benzocarbazole and Derivatives
studied their antimalarial activity but did not Benzocarbazole, Cl ~H,, N. Three isomers are
describe their prepn or determine their expl props described in Beil 20,494,495,(179) & [319] and
Re/s: l)Beil- not found 2)A.T.James & E.E. five isomers are given in the CA Decennial Sub-
Turner,JCS 1950,1515 & 1518 & CA 45,1116(1951) ject Index 41~50, 1652s(1947-1956)
Nitrosobenzocarbazoie, Cl ~H, ON. NO. Two iso-
Benzimidazolon.guanylimide [ called 1.2-0
mers are described in Beil 20,495 & 496
-Phenylen-biguanid or BenzimidazoIyl-( 2)-guanid- Mononitrobenzocarbazole, C,~H10N202. One i so-
in in Ger] , /NH\ er is described in Beil 20,(179)
C6Ha ,C:N.C(:NH).NH2; mw Dirzitrobenzocarbazole, C, ~H9N304. One isomer
\NH
is described in Beil 20,(179)
175.19, N 39.98%; yel lfts of the monohydrate 7’,rinitrobenzocarbazole, Cl ~H8N406, not found
(from w), mp 242° (dec) (Ref 1) or pearly Ifts, mp in Beil or CA tbru 1956
245 °(dec) (Ref 2). Other props and several methods T etranitrobenzocarbazole, Cl ~H7N5 08, not found
of prepn are given in Refs 1,2 & 3. It forms num- in Beil or CA thru 1956
erous salts, some of which have weak expI props: Pentanitrobenzocarbazole, Cl ~H6N60t o; mw
Hydrocblon”de, CeH9N5+HCl, ndls, dec gradually 442.18, N 19.01%. One isomer, x,x, x,x, x-Perzta-
ca 100°; Nitrate, C8H9N5+HN03, wh ndls, mp nitro-2,3-benzocarbazole is described in the lit-
216°(dec) and 2C8H9N5+5HN03+3 H20, CO1 erature. The compd is in the form of golden-yel
trysts, mp 178° (dec) and Picrate, C8H9N5+C6- Ifts, mp 256°; nearI y insol in most org solvents.
H3(N02)3.0H, yel ndls, mp 269-70° (Refs 1,2 & 3) Was prepd by heating 2,3-benzocarbazole or x,x
Re/s: l)BeiI 24,118 & [62] 2)G.PeHizzari,Gazz -dinitro-2,3-benzocarbazole with mixed nitric
51, I, 98-9(1921)& CA i5,3077(1921) 3)F.E.King -sulfuric acid. Its expl props were not investigated
et al, JCS 1948,1366 & CA 43,1404(1949) Refs: I)Beil 20,(179) 2)F. Kehrmann et al,Ber
46,3716(1913)
Benzimidezolone-imide. See Amino-benzimidazole, Note: No later Refs on pentanitrobenzocarbazole
Vol l,p A 187-R to A188-L were found in CA thru 1960

Benzin, Benzine, Petroleum Benzin or Gasoline. Benzodiazoles. See under Aminoindazoles, Vol
A mixt of hydrocarbons obtd from the second por- l,p A224-L
tion of the fractional distillates, betw 70-90°, of
Benzodioxadiazine. See Benzofuroxan
crude petroleum. It is a clear COI liq of d 0.640
.0.675; insol in w but miscible with ale, eth, oils
and carbon disulfide(Ref 1). This mixt is consid- Benzodioxan and Derivatives

ered by Sax(Ref 3) to be S1 toxic but dangerous B enzodioxan (Ethylenedioxybenzene or Pyrocate-

when exposed to heat or flame. This mixt should chol Ethylene Ether), C8H*OZ; mw 136.14, 0
not be confused with benzene or benzene homo- 23.50%. This compd exists in two configurations:
!ogues. It can be used as an insecticide and as 1,3-B enzodioxarz, H = CH = -0-CH and 1,4-Ben.
H:-cH=:<H>:
a SOIV for some expls. The Germans used it dur-
;ng WW II as one of the fuels(together with O as zodioxan. ~:~:~-o--~; Bo~ forms are aro-
oxidizer) for propelling the missile of WWII cal-
led V- l(Ref 4). Benzine with Al dust and liq O m ati c oily liquids. Their props & prepn are given
as oxidizer was proposed by Stettbacher(Ref 2) in Beil 19,22,(613) & [20,21]
as a rocket propellant MononitrobenzodioxaW C~H7N04; mw 181.14, N
Refs: l)Hackh’s(1944),p 112 2)A.Stettbacher, 7.73%. The 6(or 7)-Nitro deriv of l,4-benzodioxan
Explosivst ]956,27 & 30 3)Sax(1957),p 348 (called 4-Nitro deriv by Vorl~nder and by Heertjes
4)PATR 2510(PB No 161 P70)(1958),P Ger 215, et al); ndls(from w or ale), mp 121-2°, was prepd
 B 67

by direct nitration of the parent compd(Refs 1,2, -Tetranitro- 1,2-ethylenedioxybenzene by Heert jes
3&4) et al), CeH4N401 o, mw 316.14, N 17.72%; wh
Refs: l)Beil 19,22 2)D.Vorlander,Ann 280,?06 crysts(from ale), mp 286°, expl at higher temp.
(1894) 3)P.M.Heertjes et al, Rec 60,572(1941)& Was prepd by nitration at 70° of a soln of the
CA 37,620(1943) 4)P .M.Heertjes & L.J .Revallier, 5,6,7-trinitro deriv in sulfuric acid. Expln of this
Rec 69,263(1950) compd could not be prevented during detn of its
Dinitrobenzodioxan, CeH6N206; mw 226.14, N N content
12.39%. The 6, 7-Dinitro deriv (called 4, 5-dinitro Re/s: l)Beil- not found 2)P.M.Heertjes et al,
-l,2-ethylene-dioxybenzene by Ghosh,Robinson & Rec 60,575(1941)& CA 37,620(1943)
Robinson and by Heertjes et al), It yel ndls(from
glac ACOH+ ale), mp 131-2°, was prepd by nitra- Benzofuran and Derivatives
tion of the 7-nitro deriv using a nitric-sulfuric 2,3-B enzofuran or Coumarone (Cumaron in Ger),
acid mixt of very definite concn, at 90-95°(Ref 4). HC=CH-C-0,
Its expl props were not detd(Refs 1,2,3 & 4). ,CH; col aromatic-smelling oil; fr p
HC=CH-C-CH
There were prepd later by Heertjes et al(Refs 5
below -18°, bp 173-4°, d 1.078 at 15/15°, n~
& 6), the .5,7-Dinitro deriv, It yel ndls(from acet),
mp 145.5-145.7°, indirectly via 3,5-dinitropyro- 1.56897 at 16.3°. Other props & prepn are given
catechol, because no direct method of nitraiing in the Refs. Has been used in resins(such as
coumarone-indene resin), plastics, paints and
the parent compd had been found(Ref 5), and the
varnishes
5,6-Dirzitro deriv, yel ndls(from ale), mp 185.6
Re/s: l)Beil 17, 54,(24)& [ 57] 2)Thorpe 3
-186.1°, obtd by dinitration, either directly or via
(1939),41 1 3)Kirk & Othmer 4( 1949),594-600
the mononitro deriv of 6-acetamidobenzo- 1,4-di-
Mononitrobenzofuran, C8~N 03; mw 163.13, N
oxan, followed by deacetylation and delamination
(Ref 6). The 5, 8-Dinitrobenzo-1,4-dioxane, yel 8.59%. The following isomers are described in
cqsts(from Iigroin or aq ale), mp 99.6-102.5°, the literature: 2-Nitro-, COI ndls, mp 134°(Ref 1~
was prepd by condensation of 3 ,6-dinitropyro- x-iVitro-, yel ndls, mp 85°(Ref 1~ 5-Nitro-, CO1
catechol with ethylene bromide(Ref 6). These Ifts, mp 114-115°(Ref 2) and 6-Nitro-, yel pdr,
compds were prepd as possible substituents for mp 246-7° with decompn(Ref 3)
a zo dyes and their expl props were not detd Refs: l)Beil 17,59 2)H.Erlenmeyer et alfHelv
Refs: l)Beil 19,(613) 2)B.N.Ghosh,JCS 107, 31,77(1948) & CA 42,4167(1948) 3)P.Rumpf &
1591(1915) 3)G.M.Robinson & R. Robinson,JCS C.Gansser,Helv 37,435-6(1954) & CA 49,6216
11 1,935(1917) 4)P.M.Heertjes et al,Rec 60, (1955)
572-3(1941) & CA 37,620(1943) 5)P.M.Heertjes Dirzitro-, C8H4N205 and Trinitro-, C8H3N307
et al, JCS 1954,1869 & CA 49,9655(1955) 6)P.M. Benzofurans were not found in Beil or in CA
Heertjes et al,JCS 1955,1316& CA 50,2600(1956) thru 1956
Trinitrobenzodioxan, C8~ N3 08, mw 271.14, N
15.50%. The 5,6, 7(or 6,7, 8)-detiv called 4,5,6(or Benzofurazan and Derivatives
3,4 ,5)-trinitro- l,2-ethylenedioxybenzene by Benzofurazan or 2,1, 3-Benzoxadiazole (called
Heertjes et al, Ifts or ndls (from ale), mp 156d, 3.4.Benzo-l.2.5-oxdiazol or Benzfurazan in Ger)
can,be prepd by nitration of the 6,7-dinitro compd formerly called Benzochinon-( 1.2)-dioxim or o
(Refs 1,2 & 3) or more conveniently by nitration -Chinondioxim in Ger(Ref la), HC=CH-C=N\
of the 6(or 7)-mononitro deriv(Ref 4). The 5,6,8 o;
-Trinitro-1,4-dioxan, yel ndls(from alc and from HC=CH-C=N’
isobutanol), mp 180.4-181.0°, was prepd by ni- mw 120.11, N 23.33%; peculiar-smelling ndls(from
tration of the 5,6-dinitro deriv(Ref 5). Their expl dil ale), mp 550, readily volatile in steam; sol in
props were not detd most org SOIVS. Other props & prepn are given in
R e/s: l)Beil 19,(614) 2)B.N.Ghosh,JCS ~07, Refs
1592( 1915) 3)G.M.Robinsnn & R. Robinson,JCS Re/s: l)Beil 27,568& (573) la)Beil 7,6o1 &
~ i 1,935(1917) 4)P.M.Heertjes et al,Rec 60,574 (338) 2)T.Zincke & P.Schwarz,Ann 307,40(1899)
(1941) & CA 37,620(1943) 5)P.M.Heertjes et al, 3)A.Hantzsch & W.H.Glover,Ber 39,4170(1906)
JCS 1955,1315&CA 50,2600(1956) & 40,4346(1907) 4)A.G.Green & F. M. Rowe,JCS
5,6,7,8.Tetranitrabenzo.l,4.dioxan (called 3,4,5,6 101,2456(1912) & 111,618(1917) 5)R.J.Gaughran
 I

B 68

et al, JACS 76,2234(1954)& CA 49,6238(19551 G. Tappi,AttiAccadSciTorino 75 1,459(1940)

Mononitrobenzo/urazun, C6H3Na03, mw 165.11, 4)R.J.Gaughran et al,JACS 76,2235(1954) 5)J.V.
N 25.45%. The4-Nitro deriv, lt yeI crysts(from R. Kaufman & J. P. Picard,ChemRevs 59,448(1959)
nitric acid), mp 98°; insol in w; sol in most org Dinitrobenzofuraxan, C6H2N406; mw 226.11, N
solvents. Was prepd by treating benzofurazan 24.78%. Three isomers are described in the lit-
with coned nitric-sulfuric acid. This compd is erature:
called “Furazano dells l-nitro-o-chinondiossimas 4, 6-Dinitrobenzo/uroxan (formerly called “4,5-Di-
in Ref 3 nitro- 1,3-dinitrosobenzene” ), yel ndl S( from glac
Re/s: l)Beil 27,659 2)P.Drost,Ann 307,69(1899) ACOH), mp 172°; sol in most org SOIVS. Can be
3)M.Milone & G. Tappi,AttiAccadSciTorino 75 I, prepd either by heating 2,4,6-trinitropheny lazide
458-9(1940) & CA 37, 1309(1943) at 90-100° or by nitrating benzofuroxan with a
Note: No higher nitrated derivs of benzofurazan sulfuric-nitric acid mixt at 5-20 °(Refs 1,2,3 & 9)
were found in BeiI or in CA thru 1956 or by other methods(Refs 4,8 & 11). This compd
is an expl, ca 130% as powerful as PA, but is
Benzofurezen Oxide, Same as Benzofuroxan too sensitive for use as a HE. It is stable in
storage at 80° (Ref 7). Some of its salts are more
Benzofuroxon ond Derivatives stable and less impact-sensitive expls and, there-

,
B enzofuroxan; B enzofurazarz Oxide; B enzodioxa- fore, may find use in primary expl compns.
diazine or Quinonedioxirne Peroxide (formerly cal- - The Potassium ~alt, (KDNBF),

!
led ao-Dinitrosobenzene*, which is incorrect) 02N $= CH- ‘N~O K “, mw 264.20, N 21.21%, OB
(called 3.4-Benzo4.2.5-oxdiazol-2. 5-oxyd or Benz- HC= $— =N<
furazan-l.3-oxyd in Ger), H$ =CH-<=N-~; NO= ‘1 O
HC= CH-C =N-~ to C02 ,H2~ & K20 -42.4%, red trysts, golden
HC=CH-$=N-~ or HC =CH-~=Nxo (despite 60 yel lfts(from w) (Refs 9 & 10). The following props,
H?= CH-C=N-O H~= CH-C=~O apparently for the anhydrous salt, are given in
Ref 10: mp expl at 210°, d 2.21; friction sensi-
years of research to eIucidate its structure, a-
vailable evidence is insufficient to permit a tivity- expl with fibre or steel shoe; gas volume
developed on expln 604cc/g; hygroscopicity at
choice among the various structures suggested,
hence, none can be eliminated); mw 136.11, N 30° & 90% RH- gain 0.27%; impact sensitivity,
PicArsnApp, l-lb wt 6“., initiation sensitivity- re-
20. 58%; wh ndls(from afc or w) or almost COI Ifts
(from benz), mp 72°. Other props & prepn are quires 0.30g MF or O.10g LA; sand test- 44.8g
sand crushed vs 48.Og for TNT; volubility 0.245g
given in Refs 1,2,3 & 4
Re/.s: l)Beil 7,601 and 27,(622)& [629] 2)E. per 100g water at 30°; specific heat 0.217caJ/g/°C
Noelting & A. Kohn,ChemZtg 18,1905(1894) 3)R. for temps betw -50 and +50°; staby test(see Ref
J. Gaughran et al,JCS 76,2223(1954) 4)].V.R. 10,p 263); volatility at 100 °(heat test) % loss 1st
Kaufman & J. P. Picard,ChemRevs 59,429-61(1959) 48 h= 0.03%, 2nd 48brs 0.05, no expln in IOOhrs.
6.Azid.5.nitrobenzofuroxan, C= H#604; mw According to Refs 5 & 6, its sensitivity vaIue is
betw MF & LA(See also Ref 9a)
222.12, N 37.84%; dk yel ndls(from alc), mp 89°
Silver salt, AgC6HN4 06, red trysts, mp expl on
(dec), expl violentIy when heated rapidly above
heating(Ref 2); and Sodium salt, NaC6HN406,
its mp. Was prepd by heating l,3-dinitro-4,6-di-
red trysts, mp expl on heating(Ref 2)
azidobenzene at 80-85° until the evolution of N
5, 6-Dinitrobenzo/uroxarz (formerly caIIed “4,5-Di-
ceased. Further nitration converted this compd,
nitro- 1,2-dinitrosobenzehe ”), It yel cryst(from
on standing, to nitrobenzodifuroxan, C6H2N5 06
nitric acid), mp 172°(dec); sol in benz, diffc sol
Re/s: l)Beil- not found 2)J .R.Gaughran et aI,
in ale; was obtd by Drost(Ref 2) on nitrating the
]ACS 76,2235(1954) & CA 49,6238(1955)
5-mononitrobenzo furoxan with nitric acid and
Mononitrobenzofuroxan, C6HSN304; mw 181.11,
pptg the resulting product with w. This compd
N 23.20%. The 4-Nitro, yel Ifts(from glac AcOH), forms addn products with aniline or naphthalene
mp 143 °(Refs 1,2,3 ,4a,4 & 5) and the 5-Ni~~
(Ref l)(See also Ref 6b)
deriv, yel lfts(from dil alc or benz), mp 72°, expl
4, 7-Dinitrobenzo/uroxan, yel to brn crysts(from
(Refs 1,2,4 & 5) are described in the literature
acet), mp ca 182°; sol in hot w, MeOH, acet or
Re/s: l)BeiI 7,608& 27,(623)& [629] 2)P.
benz; S1 sol in chlf or Iigroin; insol in CC14. TWO
Drost,Ann 307,54 & 65(1899) 3)A.G.Green &
methods for its prepn ate described by Borsche &
F. M. Rowe,JCS 103,2028(1913) 3a)M.Milone &
 B 69

Weber(Ref 6a) Benzohydryl Azidodithiocarbonate. See Vol l,p

Refs: l)Beil 7,608-9 and 27,(623)& [629-30] A633-L
2)P .Drost,Ann 307,55 & 57(1899) 3)A.G.Green &
F. M. Rowe,J@ 103,2029(1913) 4)E.Schrader,Ber Benzoic Acid and Derivatives
50,778(1917) 5)L.Metz,SS 23,305-8(1928) 6)ki. Benzoic Benzenecarboxylic
Acid, Acid or Pbenyl-
Rathsburg,AngChem 41,1284( 1928) 6a)W.Borsche formic Acid(called BenzoesSure or Benzolcarbon-
& H. Weber,Ann 489,291(1931)& CA 26,708(1932) s~ure in Ger), C6HS. COOH; mw 122.12, 0 26.20%,
6b)M.Milone & G. Tappi,AttiAccadSciTorino 75 I, OB to C02 -196.5%, monocl prisms, mp 121°;(sub-
460(1940) 7)Blatt,0SRD 2014(1944) 8) J. GiHis &
Iimes at 1000), fl p 121°, d 1.316, vap press lmm
J .Hoste,AnalChimActa 1,326-9(1947) & CA 42, at 96.0°; sol in alc 46.670 at 15°, in acet 55.6%
4485(1948) 9)R.J.Gaughran et al,JACS 76,2234
at 25°, in eth 40.8% at 25°, in w 0.21% at 17.5°
(1954) & CA 49,6238(1955) 9a)M.Baer, ”Pilot Plant & 2.2% at 750. According to ~ackh’s(Ref 3) benzo-
Preparation of KDNBF”, PATR 2122 ( 1955) (Conf)
ic, acid is poisonous to man but Sax(Ref 7) con-
10)PATR 1740, Rev 1(1958),261-4 ll)J.V.R.Kauf-
siders its toxicity by ingestion, inhalation or ex-
man & J. P. Picard,ChemRevs 59,448( 1959)
posure as slight. Can be prepd by the decarboxyl-
Note: Compare with info on Dinitrodinitrosobenz- ation of phthalic acid dissolved in phtlialic an-
ene under Benzene and Derivatives
hydride, or by the catalytic oxidn of toluene(Refs
1,2,4,5 & 6). Benzoic acid occurs in benzoin and
Benzohydroxamic Acid and Derivatives
in cranberries. This compd forms numerous salts
8enzohydroxamic Acid(called Benzhydroxams&zre,
and addn compds(Ref 1a)
N-Benzoylhydroxl amin or B enzyhydroxims sure in It is used as an antipyretic, antiseptic or ex-
Ger), C6H5.C0.NH.0H or C6H~.C(OH):N.0H; mw pectorant; used in calico printing and in the man-
137.13, N 10.21%; rhom Ifts(exists in two isomet- uf of aniline dyes(Ref 3). In the pure state it is
ric types), mp 124-6° & 131-2° (values reported by used as a std in acidimetry, thermometry and cal-
various investigators); ezpl or rapid heating; v orimetry. Its nitro compds have been used in the
sol in ale; S1 sol in w or eth; insol in benz. Can expl industry
be prepd by the action of hydroxylamine on the Refs: l)Beil 9,92,(54) & [72] la)Beil 9,107,(59)
esters, chloride or amide of benzoic acid and by & [83] 2)Thorpe 1(1937),678-82 3)Hackh’s( 1944),
other methods(Ref 1). It forms numerous addn 114 4)Kirk & Othmer 2(1948),459-77 5)0rgSynth-
compds and salts, such as the Copper salt, Cu- COIIVO1 3(1955),334 & 337 6) Faith, Keyes &Clark
(C7H6N02)2, It blue tryst which expl mildly on (1957 ),151-6 7)Sax(1957),349
heating(Ref 2) Azido. and Azides of Benzoic Acid and Derivatives
Refs: l)Beil 9,301,(128) & [213] 2)L.Balbiano, Azidobenzoic (called Azido- or Triazo-benz-
Acid
AttiAccadLinceiRend [ 5] 211,392 (1912) oes;ure in Ger), N3.CeH4C02H; mw 163.12, N
Mononitrobenzohydroxamic Acid,02N.C~H4.CO- 25.76%. The 2-Azido, ndls(from w), mp 146°(deck
.NH.OH, mw 182.13, N 15.38!%. Two isomers are 3. Azido, Ifts, mp 159-160° and the 4-Azido deriv,
described in the literature: Ifis, Mp 145°(dec) (Ref 2) are described in the lit-
3-Nitrobenzobydroxumic Acid, granules(from chlf), erature(Ref 1)
mp 153° (dec). Its Sodium salt, NaC7H5N204, yel Re/s: l)Beil 9,418,(168-9) & [286] 2)S.Maffei &
cry st, expl on heating(Refs 1 & 3) 4-Nitrobenzo- L. Coda,Gazz 85, 1300(1955) & CA 50,9330(1956)
h ydmxamic Acid, Ifts(from boiling w) or monoclin- 3,5.Diazidobenzoic Acid, (N3 )zCGH~ .C02H, mw
ic prisms, mp 238-40°, forms numerous metallic 204.15, N 41.17%; ndls(from dil ale), mp expl
salts, some of which undoubtedly are expl(Ref 2) violently on heating; v sol in eth, readily sol in
Re/s: l)Beil 9,387 & [ 255] 2)Beil 9,389-90 hot alc; nearly insol in w. Can be prepd by treat-
3)J.Meisenheimer & E. Patzig,Ber 39,2542(1906) ing an ammoniacal soln of 5-azido- l-c arboxybenz-
NO te: Dinitro-C7H~N306 and “Trinitro-C7H4N408 ene-3-diazoniumperbromide with HCI
Re/s: l)Beil 9,419 2)P.Griess,Ber 21,1564 (1888)
Derivs were not found in Beil or in CA thru 1956
Note: A number of azidophenylesters and their ni-
trated derivs of benzoic acid have been described
Benzohydroxytriazine. See under Benzotriazine
in the literature: Beil 9,119,379 & 391 and (169)
Benzoyl Azide or Benzazide(Benzoylazoimide)
Benzohydroxytriazole. See under Benzotriazo!e
(called Benzoes&ueazid; Benzoylazid or Benz-
 t

B 70

azid in Ger), C6H5.C0.N3; mw 147.13, N 28.56%; 3(OY m)-Nitrobenzoyl Azide, wh Ifts(from aIc), mp
CO1 plate s{from acet), mp 32°, expl on further heat- 68°, expl on further heating; easily sol in eth,
ing; sol in eth, SI sol in alc insol in w. Curtius benz, alc or ACOH; insol in w. Can be prepd by
(Ref 2) observed the compd had a pungent odor, diazotization of 3-nitrobenzoy1hydrazine or its
was poisonous and attacked the skin, while Werle reaction with benzenediazonium sulfate(Refs 1&
& Friend(Ref 6) reported an effect of lowering the 2) and by other method s(Refs 3,5,6 & 8). This
blood press and producing IO times as much bio- compd can be used as an identifying reagent for
logical action as Na azide. Can be prepd by add- amines(Refs 4,5 & 7) and phenols(Refs 5 & 6)
ing Na nitrite and AcOH to an ice-cold aq soln of Refs: l)Beil 9,388 2)A.Struve & R. Radenhausen,
benzhydrazide. Other methods of prepn and props JPraktChem 52,228(1895)& JCS 70 1,35(1896)
are given in Refs 1,2,3 & 4 3)V.V.Vasilevskii et al, ZhObshchKhim 5,1652
Benzoylazide is extremely sensitive to impact ( 1935)& CA 30,3416(1936) 4)Kwang-Chun Meng
or friction, exploding even when pressed with a & P. P. T.Sah,JChineseChemSoc 4,75( 1936) & CA
glass rod. The crude prod expl at ca 150° and its 30,8181(1936) 5~.Veibel & H. Lillelund,Dansk-
sensitivity is increased by small amounts of im- TidsFarm 14,236(1940)& CA 35,2441( 1941); 17,
purities or by confinement. Bergel(Ref 3) describ- 183(1943} ChemZtr 19441,173 & CA 39,1608
ed two explns which took place during its prepn ( 1945) 6)P.P.T.Sah et al, JChineseChemSoc 13,
by the Gattermann-Wieland method from ethylbenzo- 22( 1946) & CA 42,148(1948) 7 )K-iJ.Karrman,
ate SvenskKenTid 60,61(1948)& CA 42,5804(1948)
The Raman spectra(Ref 5) and dipole moment 8)J.Munch-Peterson, ActaChemScand 5,1408(1951)
(Ref 7) of benzoyl azide have been detd & CA 46,8634-5(1952) and OrgSynth 33,53(1953)
Re/.s: l)Beil 9,332 & [219] 2)T.Curtius,Ber 23, & CA 49,7521(1955)
3029(1890) & JCS 60 I,56(1891);JPraktChem 50, 4(0 r p)-Nitrobenzoyl Azide, CO1 lfts(from ale+ w),
286(1894) & JCS 68 1,33(1895) 3)F.Bergel,Ang- mp 7 1-2°; soly similar to the meta deriv; can be
Chem 40,974(1927) & CA 2 1,3463(1927) 4)V.V. prepd by procedures simiIar to those used for
Vasilevskii et al, ZhObshchKhim 5, 1652(1935) ortho and meta derivs(Refs 1,2 & 5) and by the
& CA 30,3416( 19~6) 5)Yu.N.Sheinker & Ya.K. reaction of p-nitrobenzoylchloride and Na azide
Syrkin,IzvestAkadN,SerFiz 14,478(1950) & CA 4!5, soln(Re’f 4). This compd can be used as a reagent
3246( 1951) 6)E.Werle & R. Friend, BiochemZ 322, for identification of amines(Ref 3) and phenols
506(1952) & CA 46, 10440(1952) 7)E.A.Shott (Ref 3)
-L’tiova & Ya.K.Syrkin,DoklAkadN 87,639(1952) Refs: l)Beil 9,4oo 2)A.Struve & R. Raden-
& CA 47,6203(1953) hausen,JPraktChem 52,232(1895) & JCS 70 I,
Mononitrobenzoyl Azide, 02 N.C6H4 .C0.N3; mw 35(1896) 3)P.P.T.Sah et al,Rec 58,595 & 1013
192.13, N 29.16%. Three isomers are described in ( 1939)& CA 33,6746(1939) & 34,1583(1940) and
the literature: Rec 59,231(1940) & CA 34,5786(1940) 4) J. Munch
2(or o,J-AJitroberzzoyl Azide, yel prisms(from eth), -Peterson,ActaChemScand 5, 1408(1951)& CA 46,
mp 36-9 °(dec); readily SOI in eth, chlf or beniq 8634-5(1952); OrgSynth 33,53-5(1953) 5) K. Hutton,
diffc sol in petr eth. Can be prepd from 2-nitro. JOC 20,858(1955) & CA 50,5674(1956)
benzoylhydrazine in dil HN03 soln and aq NaNu2 Dinitrobenzoyl Azide, (02N)2C6H3 .C0.N3; mw
or with benzenediazonium sulfate and by other 237.13, N 29.54%. TWO isomers are described
methods(Refs 1,2,3,4 & 5). This compd can be in the literature:
used as a reagent for the identification of phenols 4, 6-Dinitrobenzoyl Azz”de,(2,4-Dinitrobenzoyl
(Refs 5 & 6) Azide), It ye] tryst, mp 68°(dec~ SOI in common
Re/s: l)Beil 9,376 2)A.Struve & R. Radenhauser, org SOIVS but in sol in aliphatic hydrocarbons;
JPraktChem 52,231(1895)& JCS 70 1,35(1896) was prepd from 4,6-dinitrobenzoylchloride and
3)V.V.Vasilevskii et al,ZhObshchKhim 5,1652 aq Na azide. Its expl props were not investigated
(1935) &CA 30,3416(1936) 4)C.Naegeli et al, (Ref 2)
HeIv 2 1,1137(1938)& CA 33,540(1939) 5)P.P. Re/s: l)Beil- not found 2)C.Naegeli et al,Helv
T.Sah & Wen-Hou Yin,Rec 59,238(1940)& CA 34, 21,1138(1938) & CA 33,540(1939)
5786( 1940) 6)P .P.T.Sah et aI,JChineseChemSoc 3, 5-Dinitrobenzoyl Akide, wh tryst ppt, mp 107°,
13,22(1946) & CA 42148(1948) expl on further heating; sol in alc or eth; insol
 B 71

in w; was prepd from 3;5-dinitrobenzoyl hydra- yi- a (or IH)-tetrazole], H5C6.$-N(N:CH.C6H5 )-~;
zide and Na nitrite in ACOH soln(Refs 1 & 2) or N N
byother methods(Refs 3,5,6&7). This compd COI ndls, mp 105°, which expl mildly on heating
can be used for the identification of phenols ~e- above mp
cause it forms dinitrophenylurethanes having Refs: l)Beil 9,(136) 2)R.Stol16 & F. Helwerrh,
definite mp’ s(Ref 4) Ber 47,1139( 1914) & JCS 106 1,750(1914)
Refs: lJBeil 9,4J5 2)1. CurCius.& A. Riedel,
JPraktChem 76,246(1907) & JCS 92 1,970(1907) Nitro and Other Derivatives of Benzoic Acid
3)J,J.Blanksma & G.Verberg,Rec 53,989(1934) Mononitrobenzoic Acid @fNBAc), 02N.CeH4.CO-
& CA ~9,462(193s) 4)P. P. T.Sah & Tsu-Sheng OH; mw 167.12, N 8.38%, OB to C02-119.7%.
h@ JChineseChemSoc 2,159( 1934) & CA 29,465 Three isomers are described in the literature:
(1935) 5)H.Degiorgi & E.V.Zappi,BullFr[ 5]4, 2-Nitrobenzoic Acid, COI ndls(from w), mp 144
1636(1937) & CA 32,518-9(1939) 6)L.I..Smith & -8°; Q: 730-735 kcal/mol(Refs 1 & 6) 3-Nitro-
J.A.Sprung,JACS 64,433(1942) & CA 361932(1942) benzoic Acid, monoclinic yel prisms, mp 140-10;
7)A.A.Bothner-By & L. Friedman,JACS 73,5391-2 Q: 729kcal/mol(Refs 2 & 5) Nishi & Toki(Ref 4)
(1951) &CA 47,515(1953) investigated a number of methods of its prepn from
2,4,6.Trinitrabenzoyl Azide, (02N)a C6H2.C0:N3; benzaldehyde and noted that reaction with nitric
mw 282.13, N 29.79%; CO1 cryst(from methyl acet), -sulfuric acid mixts above 100° led to explosions
4-Nitroberzzoic Acid, Ifts(from boiling w), mp 238
mp 92-6 °(dec) (Ref 2) to 98°(dec) (Ref 3), expl at
higher temps; d 1.673 at 20°(Ref 2); sol in acet -40°; Q~ 728kcal/mol(Ref 3)
Re/s: l)Beil 9,370,(150) & [242] 2)BeiI 9,376,
or aromatic hydrocarbons; insol in aliphatic hydr-
(153) & [247] 3)Beil 9,389,(157)& [256] 4)T.
carbons(Ref 3); can be prepd by adding aq Na
Nishi & H. Toki,JSocChemInd(J span) 45,Suppl-
azide soln in methyl acet to a stirred soln of
Binding 37-8( 1942) & CA 44,11099(1950) 5)Y.
2,4 ,6-trinitrobenzoyI chloride in methyl acet at
Hirata & T. Goto,ResRept,Nagoy aIndSciResInst
-5 to 0° (higher temps must be avoided)(Ref 2).
NO 6,37(1953) & CA 49,2363(1955) 6) T. Kosuge
This compd decomposes at RT and especially
& S.Miyashita,PharmBull(Japan) 2,397(1954) &
rapidIy in soln
CA 50,12057( 1956)
Vasilevskii et al(Ref 2) studied the expl props
Nitrosonitrobenzoic Acid, 02 N. C6H3(NO).CC)2H;
of this compd from the viewpoint of its structure
mw 196.12, N 14.29y& The 2-Nitroso-4-nitro deriv
and from measurements of N evolution at 20° &
It grn-yel Ifts(from et acet), mp above 300°(Refs
35° and found the trinitro deriv and benzoyl azide
1,3 & 4) the 4-Nitroso-2-nitro deriv, yel cryst(from
to have the same order of stability. However, both glac AcOH), mp darken at 210° and ca 230°(dec)
compds were less stable than the ortho=nitro and on rapid heating(Refs 2 & 4) and the 4-Nitroso-3
meta-nitro derivs; the meta- or 3-nitrobenzoyl -nitro derz”v, mp 170 °(dec) (Ref 5) are described in
azide was the most stable daiv the literature
Re/s: l)Beil- not found 2)V.V.Vasilevskii et al, Re/s: l)Beil 9,411 & [279] 2)Beil 9,[278] 3)P.
ZhObshchKhim 5, 1652( 1935)& CA 30,3416(1936) Friedl~nder & P. Cohn,Ber 35, 1267( 1902); Montash
3)C.Naegeli et al,Helv 21,1138-9(1938)& CA 33, 23,561(1902) & JCS 82 1,792(1902) 4)G.Heller,
54q1939) JPraktChem 106,12( 1923)&CA 17,3867( 1923)
Benzoyl Azide.Benzalhydrazone, or Benzoyl 5)E.Borel & H. Deuel,Helv 36,806(1953)& CA 47,
Azide-J3enzylidenehydrazone C6H5.CO(N3):N- 9220(1953)
.N:CH.C6H5; mw 265.27, N 26.40%; yel ndls Dinitrobenzoic Acid (llNBAc), (02 N)ZC6H3 .C02M
(from eth or ale), mp 72°, expl on heating rapid- mw 212.12, N 13.21%. The following six isomers
ly above mp; sol in alc or eth; insol in w;was are described in the literature: 2, 3-Dinitro-, small
prepd by the action of an aq soln of Na nitrite trysts, mp 201°(Refs 1 & 18); 2,4-Dinitro-, ndls,
and dil HC1 on an alc-eth suspension of benzal tablets or prisms, mp 180-3 °(Refs 2,16,17 & 19)
-benzohydrazidine (or a -hydrazino-dibenzylidi- 2,5-Dinitro-, monocl prisms, mp 177-9°(Ref 3 &
nehydrazine), H2N.NH.C(C6H~):N.N: CH.C6H~. 18) 2, 6-Dirzitro-, ndls, mp 201-3 °(Refs 4 & 18)
On heating benzoylazide -benzalhydrazone in alc 3,4-Dirzitro-, ndls, monocl prisms, mp 161-5 °(Ref
soln, there was formed 1-B enzalarnino-5-p benyl 5) and 3, 5-Dinitro-, monocl prisms, mp 202-5°
1,2,3, 4-tetrazole or [ 1. Benzylidineamino- 5-p ben- (Refs 6,8 & 15). For prepn and other props, see
 1

B 72

the Refs indicated USP 1887919(1932) & CA 27,1513(1933) 10)W.

All of these isomers form nitrophenyl esters Br~n,USP 1971029(1934) & CA 28,63 14(1934)
and numerous salts, the following of which are ll)W.Br~n,USP 1991730(1935) & CA 29, 2360
the more important expls: (1935) lla)R.Schmitt,MP 27,150(1937) & CA 31,
Batiurn Salt of 3,5-D z’nitrobenzoic A cid(Barium-3; 8199(1937) 12)M.Schaefer,MP 27,153(1937) & CA
5-dinitrobenzoate), B a(C7H3N206)2+ 5H20; It yel 31,7864(1937) 13)R.McGill,OSRD 830(1942 ),P33
ndls, mp 201-6°, expl mildly above the mp(Refs 14)P.H.Burdett & G. M. Calhoun,USP 2345868(1944)
6 & 6a) & CA 38,4806(1944) 15)F.Weygand & H. Hofmann,
Normal Lead Salt of 2,4-Dinitrobenzoic Acid(N ChemBer 83,4~5(1950) & CA ~,10051-2(1950)
-L ead-2,4-dinitrobenzoate), [(02N)2C6H3COOl~ 16)G.Machek,OsterrChemZtg 54, 182(1953) & CA
P b; fine ndls; was prepd by Schaefer(Ref 12) from 49,2363(1955) 17) J. P. Blanchatd & H. L. Goering,
a soln of Pb acetate and an alc soln of 2,4-dinitro - JCS 1954,2977& CA 49, 10880(1955) lg)T-
benzoic acid. Its expl props were not investigated, Kosuge & S. Miyashita,PharmBull( Japan)2,397
but Schmitt(Ref 1 la) found it stable at 300° (1954) & CA 50,12057(1956) 19)C.Maminuzzi
Normal Lead Salt of 3, _5-Dinitrobenzoic Acid(N & A. Vecchi,Gazz 82,671-3(1954) & CA 48,9344
-L cad-3, 5-dinitrobenzoate), brn amor pdr, mp 300 (1954)
-5 °(dec); can be prepd by treating 3, 5-dinitro- 2,4.Dinitrobenzoic Acid; 6,6.Azoxy. or 2,2’.Azoxy

benzoic acid with Pb acetate in alc soln(Ref 13) .4,6.dinitrobenzoic Acid. See below under 6-Ni-
or with Pb nitrate and NaOH solns(Ref 14). This troso-2,4-Dinitrobenzoic Acid
salt is an expl about 34% as powerfuI as TNT(by Dinitrobenzoic Acid Hydrozide or Dinitrobenzoyl*
BalMort test) and of about the same sensitivity as hydrazide, (02N)ZC6H3.C0.NH. NH2; mw 226.15,
TNT; its thermal stability is satisfactory and N 24.78%. Two isomers are described in the lit-
hygroscopicity at 90% RH is negligible(Ref 13). erature: 2,4-Dinitrobenzoic Acid Hydrazide (2,4
Brh(Ref 9) and later Burdett & Calhoun(Ref 14) -Dinitrobenzoic Acid Hydrazide), orn-yel tryst
recommended the use of this salt as an ingredi- (from abs ale), mp 231-3°; was prepd in small
ent of priming compns, such as Pb-dinitrobenzo- quant by treating the methyl or ethyl ester of 2,4
ate 8, LSt 40, tetracene 2, Pb nitrate 30 & glass -213Z -dinitrobenzoic acid with hydrazine sulfate(Ref 3)
Basic Lead Salt of 2,4-Dinitrobenzoic Acid(/3 3, S-Dinitrobenzoic Acid Hydrazide(called 3 .5-Di-
-Lead-2,4-dinitrobenzoate), (02N)2CGH~ .COOPb- nitro-benzoylhy drazid in Ger), yel ndls(from ale),
(OH); trysts, mp expl on rapid heating to high mp 158°; was prepd by heating the ethyl ester of
temp; was prepd as mono and dibasic Pb salts by 3 ,5-dinitrobenzoic acid with hydrazine hydrate in
treating 2 ,4-dinitrobenzoic acid with a Pb compd. abs ale. The Sodium salt, N aC7H5N4 05, brn crys~
Br~n(Ref 11) proposed the use of basic lead di- decrepitates on heating(Refs 1 & 2)
Refs: l)Beil 9,414 2)T.Curtius & A. RiedeI,J-
nitrobenzoate as an ingredient of priming compns,
PraktChem 76.243(1907) 3)G.Carrara et al,Gazz
together with MF, Ba nitrate and an abrasive
82,652 (1952) & CA 48,6424(1954)
Basic Lead Salt of 3,5-Dinitrobenzoic Acid(~
6-Nitroso-2,4.Di nitrobenzoic Acid or 2-Nitroso-4,
-Lead-3, 5-dinitrobenzoate), trysts, mp expl on
6.CSinitrobenzoic Acid, (02 N)zCGHz(NC)).C02H;
heating to high temp; was prepd by the action of
mw 241.12, N 17.43%; grn ndls, mp 200.5°; easily
Pb nitrate and NaOH on the dinitrobenzoic acid
sol in w, ale, acet, et acet or hot benz; insol in
in aq soln. Patented by Friederich(Ref 7) and by
CC14. Was obtd by Joshi & Patwardhan(Ref 4)
B~n (Ref 10) as an ingredient of priming compns
after 2 hrs exposure to sunlight of a satd soln of
SiIv ST Salt of 3, -5-Dinitrobenzoic Acid (Silver3,.
2,4 ,6-trinitrobenzaldehyde in dry benz. On warm-
5-dinitrobenzoate), AgC7H3N206; yel ndls(from
ing with w, the nitroso compd condensed to 2,2’
w), mp expl violently on heating(Refs 6 & 6a) -Azoxybis(4, 6-dinitrobenzoic acid), HOOC.C6H2-
Re/s: l)Beil 9,411 & [279] 2)Beil 9,411(166) & (N02)2 .N20.C6H2(N02 )2 .COOH, wh trysts, mp
[279] 3)Beil 9,412& [279] 4)Beil 9,412,(166)& 245°. This compd proved to be identical with the
[279] 5)Beil 9,413,(167) 6)Beil 9,413,(167)& white compound, which is an explosive by-product
[279] 6a)D.Muretow,ChemZtr 42,19(1918) 7)W. of continuous TNT manuf and whose constitution
Friederich,BritP 192830(1921)& JSC142,332A had not been previously established. The white
(1923) 8)P.P .T.Sah et aI, SciRptsNatlTsinghuia compd was formed also from the trinitrobenzalde-
Univ A2,137(1933) & CA 28,118(1934) 9)W.Br~n, hyde by elimination of O. The previously report-
 B 73

ed yel-brn subst, mp 229° (dec), of Sachs & Ewer- or by chromic-sulfuric acid at 50-60°(Refs 1 & 2).
ding(Refs 1 & 2) and of Secareanu & Lupas(Ref The 2 ,4,5 -TNBAc is converted by boiling w into
3) was found by Josi & Patwardhan(Ref 4) to be 2 ,4-dinitro-5-hydroxybenzoic acid(mp 1880), a
the crude “white compds of above formula mild expl(Ref 3). It forms a Lead salt, ,PB(C7H2-
Refs: l)Beil 9,417 2)F.Sachs & W. Everding,Ber N30~)2 which dfgrs at 170°(Refs 3 & 4) and a
36,962(1903) 3)S.Secareanu & 1. Lupas,BullF~5] Sjlver salt, AgC7H2N30e, yel tryst pdr (from w),
3,1161(1936) & CA 30,8181(1936) 4)S.A.Joshi & which expl on heating(Ref 2)
W.D.Patwadhan,CurrentSci(India) 22,239(1953) & Re/s: l)Bei19,(168) 2)M.Giua,AttiAccadLincei-
CA 48, 13656(1954) Rend[5] 23JI,488(1914) & Gazz 451,350 & 355
TRINITROBENZOIC ACID (TNBAc),(02N)3C6 H2- (1915) 3)R.Schmitt,hIP 27, 150(1937)& CA 31,
.C02H; mw 257.12, N 16.34%, OB to C02-46.7%. 8199(1937) 4)h(.Schaefer,MP 27,154(1937) & CA
Six isomers are possible, all of which are de- 3 1,7864(1937)
scribed in the literature: 3,4,!kTrinitrobenzoic Acid, grn-yel ndls+(C2H5 )2-
2,3,4 (or 4,5,6)sTrinitrobenzoic Acid, prisms(from O(from eth), mp 168°(dec); can be obtd by oxidn
w or benz), mp 202-3°, expl when ca 1 g or larger of 3,4,5-TNT with chromic-sulfuric acid at 60°
quant is heated; readily sol in alc or acet; sol in (Refs 1 & 2), It is converted by boiling w into
w or benz; diffc sol in chlf; insol in petr eth; can 3,_5-Dinitro-4-hYdroxy benzoic Acid, a mild expl
be prepd by oxidn of 2,3,4-TNT with nitric acid Refs: l)Beil 9,(168) 2)W.Koerner & A. Contardi,
at 150-200° or with chrome-sulfuric acid (Na2Crz- AttiAccadLinceiRend [5] 23 11,467(1914) & JCS
07 or K2Cr207+concd H2S04) at 50-60°(Refs 1,2, 108 1,875(1915)
3,4 & 5). 2,3 ,4-TNBAc is converted by hot w into 2,4,6. Trinitrobenzoic Acid, yel rhmb cryst(from
2,4-dinitro-3-hydroxy benzoic acid(mp 2040), which w), mp 228.5 -229°(dec), bp dec into C02 and l,-
is a mild expl(Ref 3). It forms Lead Salts(Ref 4) 3,5-TNB; Q~667.7kcal/mol & Q; 95.lkcal/mol
and a Silver salt, AgC H N O (Ref 23); sol in w 2.05% at 23.5° & 4.18% at 50°
on heating above *30d(R~f ~, e’ ‘dls’ which expl (2,4,6-TNBAc dec in boiling w into 2,4,6-TNB
Re/s: l)Beil 9,(167) 2)M. Giua,AttiAccadLincei- and COZ); sol at 25q in et acet 21.05, acet 22.12,
Rend [5] 23 11,486(1914) and Gazz 451,348 & 354 95% alc 27.53, abs alc 26.59, methanol 50.60,
(1915) 3)R.Schmitt,MP 27,132(1937) & CA 31’, benz 0.308, chlf 0.371, anhyd ether 14.71, CS2
8199(1937) 4)M.Schaefer,MP 27,154(1937) & CA 0.07, CC14 0.07 and toluene 0.376%(Ref 5); ther-
31,7864(1937) 5)F.ChaHenger & P.H.Clapham, mal decompn in various SOIVS was studied by
JCS 1948,1612&CA 43, 1733(1949) Moelwyn-Hughes & Hinselwood(Ref 6) over temp
2,3,5(or3,5,6)*Trinitrobenzoic Acid, lfts+2H20 range of 70°; its dissocn constant in ethanol at
(from w), mp 82 °(for dehydrate), 170°(for anhyd 35° is 1.7 x 10-4 and Q activation 27kcal/mol
compd); can be obtd by oxidn of 2,3,5-TNT with (Ref 15); coned NH~ causes immed decompn(Ref
chromic-sulfuric acid mixt at 50 °(Refs 1 & 2). It 7); elec conductivity was studied by R adulescu
is a powerful expl & Jula(Ref 8) and by PhiHips & Lowy(Ref 12);
Refs: l)Beil 9,(168) & [285] 2)W.Koerner & A. absorption spectra in vtmious SOIVS were detd by
Contardi,AttiAccadLinceiRend [5]24 1,893(1915) Radulescu & Alexa(Ref 11); molar refraction by
& JCS 108 1,790(1915) Radulescu et al(Ref 16); and its spectroscopic
2,3,6(or 2,5,6)* Trinitrobenzoic Acid, ndls+2Hz0 data(UV, visible & IR ) and polarographic measure-
(from w), mp 55°(for dehydrate), 160°(for anhyd ments were detd by Perret & Holleck(Ref 28)
compd); can be obtd by oxidn of 2,3,6-TNT with TNBAc can be prepd by the oxidn of 2,4,6-TNT
chromic-sulfuric acid at 60-80°(Refs 1 & 2). On with chromic-sulfuric acid mixt as 40-50°(Refs 1,
heating above 160° or by heating in boiling w, it 13 & 19) and is also formed in the photochemicaI
is converted into 1,2,4-TNB. The 2,3 ,6-TNBAc is decompn of TNT(Refs 4 & 13), as well as during
a powerful expl the manuf of TNT, as a result of its oxidn by ni-
Re/s: l)Beil 9,(168) 2)W.Koerner & A. Contardi, tric acid. Methods of prepn are also described by
AttiAccadLinceiRend [5] 25 II, 348(1916)& JCS Brown(Ref 20) and by Kastens & Kaplan(Ref 25).
112 1,86(1917); Gazz 47 1,238(1917) Since small amts of TNBAc form during the nitra-
2,4,5(or3,4,6).TrinitrobenzoicAcid, coI Ifts tion of toIuene to TNT, and in the presence of
(from w), mp 194.5°, readily sol in alc or eth; moisture react with metals to form trinitrobenzo-
sol in benz; v sl sol in petr eth; can b’e prepd ates, TNBAc must be removed from crude TNT.
by oxidn of 2,4,5-TNT by nitric acid at 150-160° This can be accomplished by washing the TNT
 I

B 74

with hot w, followed by the sellite treatment of mp 218°(dec) and they also obtd other unstable
TNT. According to Krauz & Turek(Ref 4), alI derivs. Identification of TNBAc by reaction with
metallic trinitrobenzoates, except the Hg compds, std chromous chloride soln is suggested by Bottei
are sensitive ‘expls and even in small quants con- & Furman(Ref 27). Krauz & Stepanek(Ref 9) pro-
siderably increase the sensitiveness of TNT. posed separating 2,4,6-TNBAc from PA by pptg
Therefore, the possibility of such salts being the acid as the silver salt, Ag(C7H2N30~ ), and
formed must be avoided PA as the nitrone pi crate, C6H2(N02)30H.Czo-
2,4,6- TNBAc Explosive Properties. It is about H6N4
as powerful & brisant an expl as TNT; Sensitivity Uses. In addn to its uses as an expl, Yoshin-
to Impact is comparable to that of TNT; its Bal- aga(Ref 24) patented the use of 2,4,6-TNBAc, a-
listic Mortar value is 98% TNT; and its Thermal lone or mixed with a fatty acid, Iithophone, talc
Stability is somewhat lower than that of TNT as & pine tar as an aide in the vulcanization of rub-
shown by Heat and Vac Stab tests(Refs 17 & 19a] ber compds. Smith & Wilkins(Ref 26) proposed the
Because of the hydroscopic nature of TNBAc, it use of highly purified 2,4,6-TNBAc as a primary
forms expl salts with the foIlowing metals: alum- std in acidimetry
inum, barium, bismuth, copper, iron, lead, mercury Re/s: I)Beil 9,417,(168) & [285] 2) F. Tiemann
silver & tin, all of which(except Al, Bi & Sn) are & W. E. Judson,Ber 3,224(1870) 3)A.Hantzsch &
tryst substs and all expl on shock or by heat(Ref H. Kissel,Ber 32,3143(1899) 4)C.Krauz & O. Turek
4). Props of the more important salts are as fol- ChemAge 13, 392(1925) & CA 20,824(1925) and
lows: Chim&Ind(Paris),Spec No Sept 1926,pp 543-7 &
Batiurn 2,4, 6-Trinitroherzzoate, Ba(C7H2N308)2, CA 2 1,651(1927) 5)L.Desvergnes, MonSci [5] 16,
dk brn-red ppt, mp expl; extremely diffc sol in w, 201(1926) & CA 21 ,740(1927) 6)E.A.Moelwyn
giving a red color(Refs 1,3 & 4). Lead 2,4,6 -Tri- -Hughes & C. N. Hinselwood,PrRoySoc 131 A,186
rzitro benzoate, [(02N)3 C6H2COO]2Pb, ndls(from (1931) & CA 25,3226(1931) 7)S.Secareanu,BuHFr
dil ale) or It cream solid, mp chars at 130° & de- 53,1395(1935) & CA 28,4048(1934) 8)D.Radulescu
flgr at 260°(Ref 17); expl at 179°(Ref 13); readi- & O. Jula,ZPhysChem B26,395(1934) & CA 28,7136
ly sol in cold w, diffc sol in ale; can be prepd by ( 1934) 9)C.Krauz & J. Stepanek,ChemObzor 9,137
reacting 2,4,6-TNBAc with lead acetate in alc (1934) & CA 28,7203(1934) 10)W.Br~n,USP 1971-
(Refs 4,14 & 17). It is an expl about 70% as power 031(1934 & CA 28,6314(1934) ll)D.Radulescu &
V. Alexa,BuIISocChim(Romania) 17, 69(1935) &
ful as TNT and is comparable in sensitivity to
CA 30,21 11(1936) 12)J.Phillips & A. Lowy,Trans
tetryl(Ref 17). The Lead+Lead Oxide salt, Pb(C+
EIectrochemSoc 71, 10pp(Preprint) ( 1937) & CA
H2N308)2+Pb0, red pdr, expl on contact with a
31 ,2105(1937) 13)R.Schmitt,MP 27,150(1937) &
hot wire and by impact or friction(?lef 1). Br~n
CA 3 1,8199(1937) 14)M.Schaefer,MP 27,154(1937)
(Ref 10) patented the use of the Nitroic Lead Salt
& CA 31,7864(1937) 15) F. H. Verhoek,JACS 61,
o{ TNBAc or of Lead Dinitrobenzoate Nitrate in
186(1939) & CA 33,2023(1939) 16)D. Radulescu
priming compns. Nickel 2,4, 6- Trinitrobenzoate,
et al, BullSocStiinteCluj 9,215(1939) & CA 33,9298
Ni(C7H2N30e)2, COI tryst powd, weak expl; read-
(1939) 17)R.McGiH,OSRD Rpt 830( 1942),P 35
ily sol in w, diffc SOI in aIc(?7ef 4). Silver 2,4, -
18)R.K.Abbott, Jr, IowfitateCollJSci 18,3(1943) &
6- Trinitrobenzoate, Ag(C7H2N30B ), Ifts or lamin-
CA 38,62(1944) 19)OrgSynthCollVol 2(1943),95
ates, mp expl above 230°; diffc sol in alc or w
19a)Blatt,0SRD 2014( 1944) 20)D.J .Brown,JSCI
(Refs 2 & 4). Tballous 2,4, 6-Trinitrobenzo ate,
66,168(1947) & CA 41,7387(1947) 21)G.D.Parks
T1(C7H2N308), tryst ppt, mp 160-3 °(dec); was
& A. C. Farthing,JCS 1948,1277 & CA ~~,592
prepd from 2 ,4,6-TNBAc and thallous hydroxide;
( 1949) 22)H.Gilman & R. K. Abbott, Jr,JACS 71,
in boiling pyridine soln, the salt decarboxylates
659(1949) & CA 43,3352(1949) 23) L. M6dard &
smoothly to 1,3 ,5-TNB and thallous oxalate. The
M. Thomas,MP 31,179,189 & 196(1949) & CA 46,
TI salt reacts further with TIOH giving a blood
11684(1952) 24)H.Yoshinaga, JapP 1543(1950) &
-red complex of uncertain compn which exploded
CA 46,8410(1952) 25)M.L.Kastens & J. F. Kaplan
on heating(Refs 18 & 22)
IEC 42,402(1950)& CA 44,4441(1950) 26)G.F.
2,4 ,6-TNBAc forms numerous esters and nitro
Smith & D. H. Wilkins, AnalChimActs 8,209(1953)
derivs thereof, as described in the literature.
Some of these will be discussed under Phenyl- & CA 47,12102(1953) 27)R.S. Bottei & N. H. Fur-
man, AnalChem 27, 1182(1955) & CA 49,14580
benzoate and Derivatives. Parks & Farthing(R ef
21) reduced 2,4,6-TNBAc to a compd, C7H5N30G, (1955) 28)G.Perret & L. Holleck,ZEIektrochem
 B 75

60,463(1956) &CA 50,16385(1956) son, Ber 29,1535(1896)

2,4,6.Trinitrobenzoic Acid, Anhydride or Trinitro. Anhydro.(benzoic acid.2.diazoniumhydroxide), cal-
benzoylanhydride,[(02N)3C H .cO]20; mw496.22, led Diazoniumanthranilic Acid in JCS 70 I, 541
82 (1896), ,Co,
N 16.94%, yel ndls, mp 270 (dec); SI sol in bemz.
Was obtd, together with 2 ,4,6-trinitrobenzoy lchlo- C5H4 O, mw 148.12, N 18.91%, wh
ride, on treating 2,4 ,6-trinitrobenzoic acid with a \N(!N)’
mixt of phosphorus pentachloride and oxychlo- ndls, expl violently even when rubbed; insol in
ride. Care should be taken to prevent overheat- eth; its aq soln dec slowly with the formation of
ing, which might result in an expl. Another meth- salicylic acid; can be prepd by diazotizing an-
od of prepn is given in Ref 3 thranilic acid
Re/s: l)Bei19,417 2)J.J.Sudborough, JCS 67,600 Re/s: l)Beil 16,546 2)A.R.Hantzsch & W.B.
( 1895) 3)R.Reed,Jr,JACS 77,3404-R (1955) & CA Davidson,Ber 29,1536(1896) & JCS 70 1,541(1896)
50,4071(1956) Benzoic Acid.2.diazonium(4.nitrophenyl).ether,
H02C.C6H4.N(!N) .0. Ceh4.N02, mw 287.23, N
Benzoic Acid Amide. See ?3enzamide 14.63%; wh lfts(from alc~ mp expl violently on
heating; mod sol in cold ale; insol in eth; dec in
Benzoic Acid, Benzyl Ester of. See Benzylbenzo-
boiIing w; can be prepd by treating a cold, coned,
ate
S1 alkaline soln of 4-nitrophenol with the nitrate
Benzoic Acid Chloride. See Benzoylchloride of 2-diazobenzoic acid
Re@ l)Beil 16,546 2)P.Griess,Ber 17,340(1884)
BENZOIC ACID DIAZONIUMHYDROXIDE AND & JCS 46 II,1014(1884)
DERIVATIVES Benzoic Acidc.2.diazoniumthiophenylether, H02C-
Berzzoi.c Acid Diazoniurabydroxide (called Benzoe- C~H4.N({N).S.C6H5; mw 258.30, N 10.85%; yel
s~ure-diazoniumi@toxid in Ger), HOZC.CGH4 .N- ppt, mp ca 60° with expln; dissolves unchanged
(~N).OH; mw 166.13, N 16.86%. Known primarily in cold dil NaOH or Na carbonate; can be obtd
in the form bf its salts, nitro compds, esters and by gradually adding a soln of 2-diazobenzoic
acid chloride to a cooled dil soln of sodium thio-
addn compds. These exist as 2(or ortho)-, 3(or
phenate
meta)- and 4(or para)-diazoniumly droxide d erivs
Re/s: l)Beil 16,546 2) C. Graebe & O. Schultess,
(see below)
Ann 263,3(1890) & JCS 60 11,1058(1891)
Ref~: Beil 16,544,546& 549& [297 & 298]
Salts and Other Derivatives of Benzoic Acid
Salts and Other Derivatives of Benzoic Acid.2
-3-Diazoniumhydroxide
.Diazoniumhydroxide
Benzoic Acid-3 -diazonium~droxide may be con-
Benzoic Acid-2-. Diazorziumbydroxide may be con-
sidered the parent compd of its salts, some of
sidered the parent compd of its salts, some of
which are expl(Ref 1): Chloride, H02C.C6H4. N2-
which are expl(Ref 1). Eg: Chlon”de Addn Compd,
Cl, yel-wh c~st, mp expl 105°, but when care-
H02C.C~H4.N2,Cl+ C7H4N202, wh ndIs, mp expl
fuUy heated melts at 145-1 50°; prepd by the ac-
on heating; likely to decomp in the solid state or
tion of amyl nitrate on an alc soln of the hydro-
in soln(Ref 6); Dicldoroiodide,H02 C. C6Ha.Nz-
chloride of 3-amino-benzuic acid(Ref 5); Nitrate,
ClzI, brn-yel Ifts, mp ca 108-9°(decomp & weakly
HO ZC.C6H4.N2.0.N02, wh prisms, mp expl vio-
expl)(Ref 3) Nitrate, H02C.C6H4.NZ.0.N02,
lently on heating; diffc sol in cold w; can be
almost CO1 tablets or prisms, darkens in the light, prepd by passing nitrogen oxide gases into a
mp expl violently on heating or by impact(Refs coned soln of 3-aminobenzoic acid in cold aq or
4 & 5); Nitrate Addn Compdt HOZC”C6H40NZ.0 - alc HN03(Ref 2) or by the action of nitrogen ox-
N02+C7H4N202, wh prisms or ndls(from alc+eth),
ide gases on a cold alc soln of 3-aminobenzoic
mp expl on heating ca 95°, expl by impact and acid in sulfuric acid(Ref 4); Chloroaurate, H02-
dec on exposure to light(Refs 2,4, & 5) C.CeH4 .N2.C1+AUC13 and cb~oroplatinate,2 (H02-
Re/s: l)Beil 16,545 & [297] 2)P.Griess,Ann 117, C. C6H4.N2.Cl+ptC14), salts were prepd also by
39( 1861) 3)(? ). Froehlich,GerP 87970; Frdl 4,1102 Griess(Refs 2 & 3) and are probably expl
(1874) 4)P.Griess,Ber 9,1653(1876) 5)A.Hand, Re/s: l)Beil 9,546 &[298] 2)P,Griess,Ann 120,
Ann 234,147-9( 1886) 6)A.Hantzsch & W. B. David-
126(1861) 3)P.Griess, JPraktChem 1,102 Foot-
 I

B 76

note (1870) 4)A.Hand,Ann 234,152(1886) 5)H. Benzoic Acid Hydrazonium Hydroxide. Incor-
Euler, Ann 325,302(1902)& JCS 84 1,299(1903) rectly listed in VOI 1*P 630-L for 3rd item from
5.Azidobenzoic Acid.3.diazoniumhydroxide, bottom which should read Azidobenzoic Acid
H02C.C6H3(N3).N( ~N).0H; mw 207.15, N 33.18%. Diazonium Hydroxide
It is known in the form of salts, some of which
are probably expl: Nitrate, H02C.C6H3(N3).N2 .0- Benzoic Acid Triozonides,
N02, wh prisms, obtd by treating a cold.~ighly
coned sol of 5-azido-5-aminobenzoic acid with /03,
CH- CH—---- C-COOH; mw 266.12, 0 66.16%
nitrous acid; Platinum Chloride salt,2[H02C .CG- 03’ I
H~(N3).N2.Cl]+ptCla, yel tryst, very diffc sol = CH—CH —-- CH
in w; “Tribromide, H02C.C6H~ (N3).N2.Br3, yel \oA
tryst, obtd by treating a coned so!n of the ni- Benzoic acid an% other aromatic substs add on a
trate with Br2 & HBr. Their expl props were not molecule of ozone(Oa) at each of the double bonds
investigated of the benz nucleous to form triozonides. These
Refs: l)Beil 16,548 2)P.Griess,Ber 21,1563 compds are wh camphor-like substs at low temps
(1888) & JCS 54 11,827(1888) and oils at RT. They are very unstable and tend
Salts and Other Derivatives of Benzoic Acid to dec with expl violence at RT. In water they
-4-Diazoniumhydroxide dec to form, probably, 1 mol of oxygen, 2 mols
Benzoic Acid-4-diazoniumhy may be con-
droxide glyoxal, 1 mol formic acid, and 1 mol of a dibasic
sidered the parent compd of its salts, some of acid
which are expI(Ref 1): Cblorz”de,H02C. C6H4.N2- Benzoic acid triozonide was prepd by treating
Cl, wh ndls, mp expI on heating(Refs 3 & 5); the acid in chlf and CC14 at 0-15° with ozone for
Nitrate,H02C.CGHd.N2.0. N02, wh ndls or 20 hrs. One sample of the triozonide exploded in
prisms, mp ~xpl on heating; r~adily sol in w(Refs a desiccator. This triozonide was less stable
than that of either benzylic acid, C6H5. CHz.CO-
2 & 4); and Compound, C lsH 1EN4041 pale-yel
OH or of phenethylic(phenyl-~ethyl) acid, C6~-
powd(from benz by pptn with ligroin), readily sol
CH2.CH2.COOH, which were obtd in lower yields
in hot alc or benz; insol in ligroin or eth; was
Refs: l)Beil- not found 2)H.Ruppe & H. Hirsch-
prepd by treating 1 mole of benzoic acid -4-di-
mann,Helv 14,54(1931) & CA 25, 1820(1931)
azonium chloride with an alkaline soln of 2 moles
of acetoxime. Its Silver salt, AgC, ~H, ,N404,
Benzol (e). Same as Benzene
expl violently on heating(Ref 6)
Refs: l)Beil 16,549 & [298] 2)LRemsen & R.O. Benzomethylanilide. See Benzotoluide
Graham,AmChemJ 11,326(1889) & JCS 5611,975
(1889) 3)J.W.MarshaIl,Ber 28,338(1895) & JCS BenzonitriIe and Derivatives
68 1,239(1895) 4)G.F.Weida,AmChemJ 19,556 B enzonitrile or Pbenyl Cyanide (called Benzoe-
(1897) & JCS 72 1,563(1897) 5)H.Euler,Ann 325, saurenitril, Benzonitril of PhenyIcyanid in Ger),
302(1902) & JCS 84 1,299(1903) 6)H.w.Bres~er et C61$ .CN; mw 103.12, N 13.58%; transparent CO1
al,Ber 39,879(1906)& JCS 90 1,322( 1906)
oil with almond-like odor, mp -12.9°, bp 191°,
AnhYdro@nitrobenzoic acid*4diazoniumhydrox*
d 1.01 at 15°; highly toxic but somewhat Iess
i de), co—1
so than cyanogen or hydrocyanic acid(Ref 2).
HC — ~=~H
02N.~— C-=CH 0‘\ ‘ mw 193.13, N 21.76% Its other p~ops & prepn are given in Ref 1.
N~~ ..._ ..-– .-J Benzonitrile forms numerous salts and addn
lt yel Ifts, mp expl violently on heating or impacq compds
almost insol in cold ale; can be obtd by treating Re/s: l)Beil 9,275,(121) & [196] 2)Sax(1957),
cold 3-nitro-4-aminobenzoic acid with abs alc 350
saturated with nitrous acid. The compd, in boil- Azidobenzonitrile, N3.C=H4.CN; mw 144.13, N

ing ale, gives 3-nitro-benzoic acid 38.87%. isomers are described

Three in the lit-
Re/s: l)Beil 16,550 2)H.Salkowski,Ann 173,63 erature: 2-Azido, It, sensitive, yel lfts(from petr
(1874) eth], sinters ca 51°, mp 58°; 3-Azido, lt yel ndls
 R 77

(from ale), mp 57°; and 4-Azido, ndls (from sIc), -form 26°, y -form 47°; bp 305°, vap press Imm
mp 70°. Their other props & prepn are given in at 108°; d a -form 1.098 at 50°, @-form 1. 108°;
Beil 9,418,419 & [169] toxicity details are unknown(Ref 4). Its other
Morzon.itroberzzorzitrile, 02 N.C6H4 .CN; mw 180.12, ptops & prepn are given in Refs 1,2 & 3
N 15.55%. Three isomers are described in the Re/s: l)Beil 7,410,(218) & [349] 2)A.N.Sachan-
literature: 2-iVitro, ndls(from w or glac AcOH),
en & F. D. Caesar,USP 2528789 (1950) & CA
mp llOO(Ref 1) 3- Nitro, ndls(from w), mp 115.118Y
45,2981(1951) 3)E.B.Bengtsson,SwedP 137686
sublimes on heating below mp(llef 2) and 4-Nitrq
yel Ifts(from ale), mp 146-149°(Ref 3). Their ( 1952)&CA 4,2110(1954) 4)sax( 1957),350
Azidobenzophenone, C6H .C0.C6H4.N3; mw
other props & prepn are given in the Refs
223.23, N 18.83%. The fo f lowing isomers are
Refs: l)Beil 9,374 & [246] 2)Beil 9, 385,(1.56) described in the literature: 2-Am’do, h yel
&[254] 3)Beil 9,397,(164) & [273] ndls(from abs ale), mp 36-8°, dec with a puff on
Dinitrobenzonitrile, (Oz~N)2C6H3.CN; mw 193.12, contact with sulfuric acid; prepd by diazoti zing
N 21.76%. The following isomers are described o-aminobenzophenone and adding N a azide to the
in the literature: 2, 3-Dinitro, It buff lfts(froti diazonium soln(Ref 2) and the 4-Azido, pale
aq ale), mp 97-8°(Ref 8); 2,4-Dinitro, brn-yel yel Ifts(from eth), mp 74.5°; prepd by adding am-
Ifts(from sIc), mp 103-5 °(Refs 1,4 & 7), its monia to the di azoniumperbromide of 4-amino-
reactions(Refs 4 & 5) and eutectics(Ref 7~ 2,6 benzophenone (Ref 1). Their expl props were not
-Dinitro, It brn ndls(from ale), mp 145°(Ref 2);
detd
3,4-Dinitro, It yel ndls(from ale), mp 92°(Ref 6); Refs: l)Beil 7,(232) 2)P.A.S.Smith et al,JACS
and 3, 5-Dirzitro, yeI monocl prisms(from aIc),
75,6336(1953) & CA 49,7571(1955)
mp 127-130°(Refs 3 & 9). Their expl props were
Benzophenonediazide, C6H5 .C(N3)2 .C6H ~; mw
not investigated
250.26, N 33.58%; crysts(from MeOH), mp 42°;
Re/.s: l)Beil 9,412 & [279] 2)Bei1 9,413 & [167]
3)G.M.Bemett & R. L. Wain,JCS 1936,1111 & CA unchanged by boiling w or dil alks; dec into
30,7558(1936) 4)F.R.Storrie,JCS 1937,1746 & N-a -.diphenyltetrazole when distiiled in vac
CA 32,522(1938) 5)C.W.N.Holmes & J. D. Loudon, or when heated in smyl eth and C02 atm; reacts
JCS 1940,1321 &CA 35,1776(1941) 6)H.Gold- explosively with coned sulfuric acid, even in ,the
stein & R. Voegeli,Helv 26,1126(1943) & CA 38, cold. Was prepd from benzophenonedichloride and
78( 1944) 7)H.Rheinboldt & M. Perrier,ChemBer Na azide in acet soln. This compd is considered
85,11o & 127(1952) & CA 46,7554(1952) 8)D.L. quite stable and its sensitivity to shock is only
Vivian et al,JOC 20,800(1955) & CA 50,7813 S1 greater than that of PA
(1956) 9)A.V.Kirsanov & R. G. Makitra,ZhObshch- Refs l)Beil- not found 2)S.G~tzky,Ber 64,1558
Khim 26,907(1956) & CA 50, 14633(1956) (1931) & CA 25,4543(1931)
Note: Higher nitro derivs of benzonitrile were Mononitroknzopherzone, C13H9N03, mw 227.21,
not found in Beil or in CA thru 1956 N 6.17%. The 2-Nitro, monocl prisms, w? 105°;
3-Nitro, ndls(from dc), mp 95°; and 4-Nitro deriv
Benzonitrile.3.diazoniumhydroxide, NC.CeH4.N(~-
Ifts(from abs ale), mp 138°, are described in
N). OH; known only in the form of salts. Its BeiI 7,425,426,(230)& [362]
Nitrate, NC. C6H6N2.0.N02, ndls or prisms, is Dinitrobenzophenone C1a,HeN205; mw 272.21, N
expI 10.29z. The following isomers axe described in
Refi Beil 16,548
the literature: 2,2’-Dinitro, CO1 ndls(from toluene
Benzooxytriazine. See under Benzotriazine or glac AcOHi), mp 188-9° 2,3‘.Dinitro, prisms
(from toluene), mp 126° 2,4’. Dinitro, col prisms
Benzophenone and Derivatives (from glac AcOH), mp 196-7° 3,3’-Dinitro, CO1
Benzophenone or Diphenylketone (also called a Ifts(from glac ACOH) or cryst(from MeEt ketone),
-Oxodiphenylmethane or Benzoylbenzene) (called mp 155° 3,4’-Dirzitro, CO1 ndls(from glac AcOW,
a-Oxodiphenylmethan, Diphenylketon, Benzo- mp 172-5° 4,4’-Dinitro, CO1 ndls(from glac Ac-
phenon, a -Oxo-ditan or Benzoylbenzol in Ger), OH) or prisms(from Et acet), mp 189° ~d 3,-
.5.Dinitro deriv, yel prisms(from ale), mp 131°
C6H5.C0.Ce~; mw 182.12, 0 8.78%; wh rhmb
trysts with rose-like odoq mp a -form 49°, @ Re/: Beil 7.427,428,(231)& [364]
 1

B 78

Trinitrobenzophenone, Cl ~H7N907; mw 317.21, and dec rapidly on heating to ca 115° or on heat-

N 13.25%. Only the 3,5,3’-trirzitro deriv is de- ing in soln
scribed in the literature: CO1 trysts, mp 159°; Ref: Beil 27,(240) & [47]

diffc sol in ale; was prepd by heating 3 ,5-dinitro- Dinitrobenzopbenoxazine, C ,GH9N305;

mw 323.26
benzophenone with dil nitric acid for 6 hts. N 13.00%. Three isomers are described in Beil:
Its expl props were not investigated 5, 7-Dinitro- L 2- benzophenoxazine, brn-red trysts
Refs: l)Beil- not found 2)F.Batdone,CR 236, 5, 7-Dinitro-2, 3-benzopbenoxazine, brick-red trysts
830(1953) & CA 48,2671(1954) (from toluene), mp ca 313 °(dec) and 5, 7-Dinitro
Tetranitrobenzophenone, C ,3H6N40~; mw 362.21, -3,4 -benzophenoxazine, brn-red ndls, mp ca 279°
N 15.47%. Two isomers are described in the lit- (dec)
erature: Re/: Beil 27, [46& 47]
2,4,2 ‘,4’ -7’etranitrobenzop henone[ calIed Bis(2.4 Trinitrobenzopbenoxazine, C, ~H8N4 O,, not found
-dinitro-phenyl)-keton in Ger)], yel prisms, mp in Beil or in CA thtu 1956
x,x,x, x* Tetranitro.2,3.benzophenoxazine, C, ~H7-
232°; was prepd by adding chromic oxide to
tetranitrodiphenylmethane in glac ACOH and N509; mw 413.26, N 16.95); dk-red Ifts or tablets
boiling the soln for 2 X hrs or longer(Refs 1 & 2). (from aniline), mp expl on heating; SOI in dil alk-
It was found to be less powerful and less brisant ali hydroxide with a violet COI; SOI in coned sulf-
than PA(Ref 3) uric acid giving a blood-red COI; was prepd by
Re/s: l)Beil 7,429 & [365] 2)K.Matsumara,JACS treating 10-acetyl-2 ,3-benzophenoxazine with
51,818(1929) & CA 23,1904(1929) 3)Blatt,0SRD fuming nitric acid in ice-cold glac AcOH. It forms
2014( 1944), under Nitro Compounds a dk-brn Na salt
3,5,3’, 5’-’Tetranitrobenzophenone, col trysts, Refs: l)Beil 27,(24o) 2) F. Kehrmann & A. A. Neil,
mp 250°, SI sol in ale; was prepd by treating Ber 47,3105(1914) & JCS 108 1,304(1915)
3,5,3 ‘-trinitrobenzophenone with fuming nitric
Benzophenyltriazole and Derivatives
-sulfuric acid mixt(Ref 2). Its expl props were
not detd Benzophenyltriazole or Pbenylbenzotriazole,C1 ~-
Re/s: Beil- not found 2) F. Bardone,CR 236,830 H9N3; mw 195.22, N 21.23%. (Several isomers of
( 1953)&CA 48,2671(1954) either a-v (or 1,2,3 )-triazole or ~-v(or 2,3,1)
Note: Higher nitro derivs were not found in Beil -triazole are described in Beil 26,39 & [18,46]
or in CA thru 1956 Mononitro benzopbenyltriazole, C ,2 HeN402; mw
240.22, N 23.3%. Several isomers are described
Benzophenonecarbaxylic Acid. See Benzoylbenzo- in the literature
ic Acid Re/s: l)Beil 26,39,44,(11) & [26] 2)K. Fries et
al, Ann 51 1,247(1934) & CA 28,5447(1934)
Benzophenone Peroxide. Same as Dibenzophenone
Peroxide Dinitrobenzopheny ltriazole, C, *H7N504; mw
285.22, N 24.56%. SeveraI isomers are described
Benzophenoxazine ond Derivatives in the literature(Refs 1- 4). The isomer Benzo-1
Benzopbenoxazine, C ,6H, ,NO; mw 233.26, N -(2’,4‘-dinitrophenyl)- a -v(or 1,2, 3)- triazole,
.6.01%. According to BSil(Ref 1), this compd ex- HC-CH=~–N[C6Ha(N02 )2]-~, reported to defgr
ists as the following isomers: 1,2-, 2,3 and 3,4 HC-CH=C – N
-Benzophenoxazine. CA(Refs 2 & 3) also lists 3 with evoln of flame when heated above its mp
isomers bur calls them: 5H-[a], 9H-[a] and 12H 186-7°; was prepd by treating an aIc soln of di-
-[a] -Benzophenoxazines nitroaminodiphenyl hydrochloride with Na nitrite
Refi l?Beil 27,80 & 81 & (240,241) 2)cA Decen- (Ref 2)
nial Index, Subject( 1937-46),p 4289 3)Ibid( 1947 Re/s: l)Beil 26,44,50 & (10,11) 2)W.Borsche &
-56),P 1757a D. Rantscheff,Ann 379,169(1911) 3)K. Fries et al,
Monorzitrobenzophenoxazine, C, ~H, 0N203; mw Ann 51 1,247(1934) & CA 28,5447(1934) 4)R.
278.26, N 10.0%. Two isomers are described in Andrisano & D. Dalmonte Casoni,CA 41,723(1947)
Trinitrobenzopheny ltriazole, C, ~H6N606; mw
BeiI: 7(?)-Nitro-2, 3- benzophenoxazine, brn-red
ndls(from ale), mp 222-3 °(dec); and 2-Nitro-3,4 330.22, N 25.45%. The following isomer is de-
-benzophenoxazir.ze, violet flakes, mp dec ar RT scribed in the literature: >-Nitrob eTZZO.2.(2’,4’
 B 79

-ditzitropbenyl) -/3 -v (or 2,3,1 )-triuzole (called JPraktChem 120,17(1928)& CA 22,4508(1922)

p-Nitro-o-phenyIen-azimido-o-p-dinitrobenzol by
Willgerodt), H$=CH–$=N-~[C6H 3(N02)z] ; Benzophenyitriazoie, Hydroxy -and Derivatives
02N.C=CH-C =N Hydroxybenzopbeny lttiazole(called Oxyphenyl-
yel ndls(from ACOH or ale), mp 238°. It was benztriazol in Ger), C ,2H9N90; mw 211.22, N
prepd by heating 5-nitrobenzo-2-phenyl-triazole 19.90%. Several isomers are described in Beil
with fuming nitric acid(Refs 1 & 2). Its expl 26,40(28-9) & [18,61-2]
props were not investigated’ Mononitrobydroxy benzopbenyltriazole, C, ~HaN4-
R ef.s: l)BeiI 26,45 2)C.Willgerodt et al, JPrakt- 03; mw 256.22, N 21.87%. One isomer 2-phenyl-
Chem 42,130(1890) & 56,390( 1897) -nitro-5-h ydroxy-benzotri azole is described in
Tetranitrobenzopheny Itriazole, C, *H5N708; mw Beil 26,)30)
375.22, N 26. 13%. The following isomer is de- Dinitrobydroxyb enzopbenyltriazole, C ,2 H7N505;
scribed in the Iiteratu”e: mw 301.22, N 23.25%- not found in Beil, but its
4, 6-Dinitrobenzo-2 -(2*,4 ‘-dinitropbenyl) - /3 - v(or isomer 2-Phenyl-4 ,6-dinitro-benzotri,azo le- l-ox-
2,3,1 )-triazole (called Tetranitro-pheny lazimido- ide, It yel trysts, mp 195-6°, is listed in Beil
benzol by Willgerodt), 02N $=C 26,50
;c=c(~:=N-~ .= Trinitrobydroxy benzopbenyltriazole, C, ZH6N6C)7;
[CeH~(N02)21; lt yel crysts(from Ac~H), mp mw 346.22, N 24.28%- not found in Beil, but its
195-6°; sol in AcOH, benz or toluene; diffc SO1 isomer 5-Nitro-2-(2, 4-dinitropbenyl)- benzotri-
in chlf, eth or ale; insol in w. Can be prepd by azole.3-oxide, yel trysts, mp 224°, is listed in
heating 4,6-dinitrobenzo-2-phenyl-triazole with Beil 26,45
coned nitric-sulfuric acid. Its expl props were Tetranitrobydroxy benzopbenyltriazole, C, *H5N7-
not investigated 09; mw 391.22, N 25.06%- not found in Beil, but
Re/.s: l)Beil 26,50 2)C.Willgerodt,Ber 25,2663 its isomer 2-(2,4 -Dinitro-pbenyl)-4, 6-dinitro-ben-
(1892) zotriazole-l-oxide, yel trysts, dec 192°, is Iist-
Benzophenyltriazole, Dihydro- and Derivatives ed in BeiI 26,51
Dibydroxybenzopbeny (called Dioxy-
ltriazole
phenylbenztriazol in Ger), C, *H9N302, mw Benzopyrazoles. See under Aminoindazoles, Vol
227.22, N 18.49%. Several isomers are described 1,p A224-L
in BeiI 26,(34)
Dinitrodibydroxybenzopbenyltriazole, C, ~H7N~06; Benzopyrylium Compounds. A group of compds de-
mw 317.22, N 22.08%. One isomer, 2-(3, 5-Di_~itro-2, - rived from benzo~vran.
.,. the O of which is assum-
4-dibymxy-pbeny l)-benzotriazole, is described ed to be tetravalent(Ref 2). Structural formulas
in Beil 26,[19] of the compds and salts studied are given in
Trinitro-, Cl *H6N608 and Tetrwnitro-, C, ~H5N7- Refs 1 & 3. Shriner & Moffett(Ref 1) published
0, O*D erivatives of ~ibydrozybenzopbeny ltriazole, several articles reporting their investigations of
were not found in Beil or in CA thru 1956 benzopyrylium compds. Some benzopyrylium de-
Pentanitrodihydroxybenzophenyitriazoie {called rivs, such as substituted 2, 3-Dipbenylbenzo-
Pentanitrodibydroxypb or 5, 7-Dinitro-2,
entriazole - Pyvlium percblorates, proved to be expl. Care
1,3-benzotriazol-4-ol, 2-(3 -bydroxypicryl) in CA must be exercized during their prepn and in the
and called 5,7-D initro-4-oxy-2-[ 2.4.6-trinitro-3 prepn of Pbenylflavylium p erchlorates to prevent
-oxyphenyI] -benztriazol in Ger}, expln(Ref 3)
Refs: l)R.L.Shriner & R. B. Moffett,JACS 61,
1474(1939); 62,2711(1940); 63,1694(1941) & 66,
301(1944) 2)Hackh’s(1944), 117 3)R.R.Otter &
R. L. Shriner,JACS 73,889(1951)
452.22, N 24.78%. Brn amor pdr, dec 176-180°,
deflgr ca 275°; easily sol in ale, AcOH & acet; BENZOQUINONE AND DERIVATIVES
diffc sol in hot w; nearly insol in benz. Was B enzoquinone[Quinone; o-(or)p-Dioxybenzene;
prepd by reduction of azopicric acid(hexanitro- Benzenone or Dihydrodiketobenzene], C6H602;
azophenoI) with NaSH in w mw 108.09, 0 29.60%. This compd exists as the
Refs: l)Beil 26, [61] 2)K.Elbs & O. H. Schaaf, ortho and para isomers: 1, 2(or o)-Benzoqziinone
 B 80

[called Benzochinon-(1.2 );o-Benzochinon; o (Ref 2)

-Chinon or Cyclohexadien-( 1.3)-dion-(5 .6) in Ger], Re/s: l)Beil 7, [587] 2)K.Fries & P. Ochwat,
,CH=CH, R-r 56,1303(1923) & JCS 124 1,844(1923) 3)A.
HC ,C:O; bright red /orm, transparent, Korczy6ski & St.Namyslowski, BullFr [4] 35,1190
“CH-C(:O) (1924) & CA 19,644(1925)
4-sided octagonal tablets or prisms, mp dec on 2,3,5.Triazido.6..chlor.l,4(?).benzoquinone, 0 :C6-
standing or beginning ca 60-70°; CO1 form, CO1 CI(Na)3 :0; mw 265.59, N 47.48%; red-violet tryst,
prisms, mp expl occasionally, giving off grn-brn mp-expl on heating; diffc sol in glac AcOH, but
smoke; in a little ethereal soln, changes rapidly not decompd by boiling in glac AcOH; was prepd
into the red form(Ref 1); l,4(or p)-B enzoquinone by treating 2,3, 5,6-tetrachloro- 1,4-benzoquinone
[called Benzochinon-(1.4); p-Benzochinon; p-Chi-
(Chloranil) with an excess of Na azide in boil-
non or Cyclohexadien-( 1.4)-dion-(3 .6) in Ger],
ing aIc
,CH=CH,
Refs: l)Beil 7, [587] 2)A.Korczyiiski & St.
O:c, C:O; yel prisms(from w, cold
NamysIowski,BuIIFr [4] 35,1190(1924) & CA 19,
CH= CH’
644(1925)
ligroin or petr eth), mp 115.7°, bp-sublimes; d
2,3,5,6.Tetraazido.l,4.benzoquinone, 0:C6(N3)4-
1.307; readily sol in hot w or Iigroin; mod sol in
:0; mw 272.16, N 61.76%; brn-yel to blue-black
hot w or Iigroin; mod sol in coId petr eth or cold
shiny prisms, mp -expl violently on heating and
ligroin; sol in alc or eth; SI sol in cold w. Other
props & prepn are given in Ref 2; toxicity is dis- by impact or friction; diffc sol in cold ale; de-
cussed in Sax(Ref 4). 1,4-Benzoquinone forms compd by dissolving in common org SOIVS or by
numerous addn compds and salts(Ref 3), many of Na sulfide soln, evolving nitrogen; also dis-
which are unstable and some undoubtedly are expl solves in NaOH, giving a yel-colored soln, and
Re/s: l)Beil 7,600,(337) & [566] 2)Beil 7,609, in sulfuric acid giving a grn soln, both evolving
(340) & [567] 3)Beil 7,615,(343)& [572] 4)Sax nitrogen; was prepd by treating 2-azido-3,5,6
( 1957),350& 1077 -rrichloro.1,4-benzoquinone in dil alc at 20° with
Azido and Azido Halogen Derivatives of Benzo- an excess of Na azide(Ref 3) or by carefully
quinone warming 2,5-diazido-3,6 -dichloro- 1,4-benzoquinone
2.Azido.3,5,6.trichloro.l,4.benzoquinone,0:CG- in alc with Na azide(Ref 2)
Cla(Na):O; mw 252.45, N 16.64%; dk-orn ndls Re/s: l)Beil 7, [587] 2)K. Fries & P. Ochwat,
(fro~ ale), mp 147-9° (turns brn at 14s0), expl Ber 56,1304(1923) & JCS 124 1,844(1923) 3)A.
mildly on rapid heating; was prepd by adding 1 Korczy6ski & St. Namyslowski,BullFr [4] 35,1190
mol of 2,3,5,6-tetrachIoro-1,4-benzoquinone to 1
(1924) & C.4 19,644(1925)
3,4,5,6*Tetraazid- l,2~benzoquinone, 0:C6(N3)4-
mol of Na azide in glac AcOH at 100°. By slow-
ly heating this compd near or sl above the mp, :0; mw 272.16, N 61.76%; dk-violet trysts, dec
on storage; mp expl on heating; sol in glac ACOH,
a red liq is obtd
alc or eth, with decmpn; was prepd from tetra-
Re/s: l)Beil 7,[587] 2)A.Korczyiiski & St. Namy-
slowski, BuHFr [4] 35,1189 (1924) & CA 19,644 bromo-l,2-benzoquinone and an excess of Na
azide in glac AcOH. The explosibility of the
(1925)
2,5.Diazido.3,6.dichloro.l,4.benzoquinone, 0: C6- trysts prevented their analysis
Refs: l)Beil 7, [567] 2) A. Korczyiiski & St.
C12(N~)2:O; mw 259.02, N 32.45%; vermilion
Namyslowski,BullFr [4] 35,1 190(1924) & CA 19,
crysts(from glac AcOH), mp expl violently on
644(1925)
heating; sol in xyIene with decompn; diffc sol in Nitro and Other Derivatives of Benzoquinone
aIc or glac AcOH; was prepd by treating 2,3,5,6
Monorzz’tro, C6H3N04, Dz’nitro, CGH2N205 and
-tetrachloro-l ,4-benzoquinone( Chloranil) with 4
Trinitro, C6HN30a derivs were not found in Beil
mols of Na azide in boiling glac AcOH(Ref 2) or
or in CA thru 1956
by tre sting 2-azido-3, 5,6-trichIoro- l,4-benzo- 3,4,5,6.Tetraazido.l,2.benzoquinone, 0:Ce(N02)4-
quinone with 2 mols Na azide in boiling alc(Ref
:0; mw 288.09, N 19.45%; orn-red or yel ndls
3). This compd is insensitive to friction or im- (from boiling w); soln in w is yeI; was prepd by
pact. On warming with aniIine, it gives 2,5-di- nitrating 3,4-dihydroxybenzoic acid with nitric
anilino-3,6-dichloro- 1,4-benzoquinone and a small acid, alone or in glac ACOH. Oxalic acid was
quant of a bIue-black prod which expl on heating also formed in the reaction. The expl props of
 B 81

the tetranitro deriv were not detd dissolved in acet, by treatment with acet solns
Re/s: l)Beil 7,(340) 2)F.von Hemmelmayr, of nitrous anhydride and acetic anhydride. The
Monatsh 34,815(1913)& JCS 1~ 1,728(1913) addn of eth produced a ppt which was stabilized
2,3,5,6.Tetra.(2.nitrophenylmercapto).l,4benzo. as acetylation proceeded
quinone, (02 N. C6H4.S)4C602; mw 720.74, N Refs: l)Beil 16,(373) 2)G.T.Morgan & D.A.
7.78%; bm-yel prisms(from nitrobenz), mp -expl Cleage,JCS 113,592-3(i918)
violently when heated; diffc sol in common qrg 4.Acetylimino2,6.dichlor.l.diazonium.l,4.benzo.
SOIVS; was prepd by treating tetrachloro- 1,4-ben- quinone, [called 4-Acetyl-2,6-dichloro-p-phenyl-
zoquinone( chloranil) with an excess of 2-nitro- ene-1-diazo-4-imide by Morgan & Cleage(Ref 2)
thiophenol in alc and 2.6-Dichlor-benzochinon-( 1.4)-acetimid-(4 )
Refs: l)BeiI 8, [572] 2)K.Fries & P. Ochwat, -diazid-( 1) or N-Acetyl-3 .5-dichlor-4-diazo-anilin
Ber 56,1302(1923)& JCS 124 1,844(1923) in Ger(Ref 1)], CH3.C0.N:C6H2(CI) 2:N; mw 230.05
Substituted Diazonium Derivatives of Benz. N 18.26%; almost COI plates, mp expl ca 138°;
quinone was prepd from 2,6-dichloro-p-pheny ldiamine, in
4.Acetylimino.1.diazonium.l,4.benzoquinone[cal- water, by acety~ation with acetic anhydride and
led Acetyl-p-phenylenediazoimide by Morgan & diazotization of the 4-acetylimino deriv, in acet
Upton (Ref 2) and Benzochinorr( l.4)-acetimid-di- cooled to. -15°, with nitrous anhydride in ace~
azid or N-Acetyl-4-diazo-anilin in Ger(Ref 1)], d~ eth pptd the product
CH3.C0.N:C6H4:N2 +H20; mw 179.18, N 23.45%; Re/s: l)Beil 16,(373) 2)G.T.Morgan & DA.
yel-wh trysts, very unstable at RT, mp -expl ca Cleage,JCS 113,594( 1918)
127°; “compd exploded violently in contact with 4.Acetylimino.3,5.dichlor.l.diazonium.1,4.benzo
CUO and a stream of air; was prepd by treating quinone[called l-Acetyl-3,5-dichloro-pphenylene
a well-cooled soln of N-acetyl-p-pheny lenedi- -l-diazo-4-imide by Morgan & Cleage(Ref 2) and
amine in a small amt of acet with liq nitrous an- 2 .6-Dichlorbenzochinon-( 1.4)-acetimid-( 1)-diazid
hydride. When an alcoholic soln of N-acetyl*p -(4) or N-Acetyl-2.6-dichlor-4-diazo-anilin in Ger
-phenylenediamine was treated with an ethereal (Ref 1)1, CH3.C0.N:C6H2(C1 )2:N2; mw 230.05,
soln of nitrous anhydride and more eth was N 18.26%; orn-yel tryst, very rapidly changes to
added, a pale pink crystn ppt separated. It contd
chocolate in the light, mp 133° (dec) [Form I]
23.18% N and decompd explosively at 95°
and dk-gray ppt, darkens on exposure to light, mp
Re/s: l)Beil 16,(372) 2)G.T.Morgan & A. W.-
expl 138° [Form 2]. Form 1 was prepd by diazo-
Upton,JCS 111, 193-5(1917)
tizing l-acetyl-2,6-dichloro-p-phenylenediamine
4.Acetylimino.2.nitro.l.diazonium.l,4.benzo.
(same as 4-acetyI-3,5-dichloro-p-phenylenedi-
quinone [called 4-Acetyl-2-nitro-p-phenylene-l
amine), in dry acet, with nitrous anhydride, dis-
-diazo-4-imide by Morgan & Cleage(Ref 2) and 2
solved in acet, and pptg the product by adding
-Nitro-benzochinon-( 1.4)-acetimid(4 )-diazid-( 1) or
dry eth. Form 2 was prepd from 2,6-dichloro-p
N-Acetyl-3-nitro-4-diazo-aniline in Ger(Ref l)],
-phenylenediamine, in dry acet at -10°, by diazo-
CH~.C0.N:C6H3(N02 ):N2; mw 206.16, N 27.18%;
tization with nitrous anhydride in acet and acetyl-
yel plates, darkens on exposure to light, mp expI
ation of the product with AC20
ca 142°; was prepd by treating 4-acetyl-2-ditro-p
-phenylenediamine( dissolved in dry acet and Re/s: l)Beil 16,(373) 2)G.T.Morgan & D.A.
cooled to -15°) with a 10% acet soln of nitrous Cleage,JCS 113,595-6(1918)
4.Benzoylimino.l.diazonium.l,4.benzoquinone
.anhydride, free from N peroxide
Re/s: l)Beil 16,(373) 2)G.T.Morgan & D.A. [called Benzoyl-p-phenylenediazoimide by Morgan
Cleage,JCS 113,591( 1918) & Upton(Ref 2) and Benzochinon-( 1.4)-benzimid
4.Acetylimino.3.nitro.l.diazonium.l,4.benzo- -diazid or N-Benzoyl-4-diazo-aniIin in Ger(Ref 1)],
quinone, [called 4-Acet yl-3-nitro-p-pheny lene-l C6H5. C0.N:CeH4:Nz; mw 223+23, N 18.83%; pale
-diazo-4-imide .by Morgan & Cleage(Ref 2) and 2 yel crysts(from acet+eth), mp expl ca 139°; was
-Nitro-benzochinon-( 1.4)-acetimid-( 1)-diazid-(4) prepd by treating N-benzoyl-p-pheny lenediamine
or N-Acetyl-2-nitro-4-diazo-anilin in Ger(Ref 1)1~ with a soln of nitrous anhydride in acet, cooled
CH3.C0.N:C6H3(N02 ):N2; mw 206.16, N 27.18%; in ice and salt; the product separated on pouring
brn-red plates, mp expl violently at 140°; was well-cooled eth into the soln
prepd from 4-acetyl-2-nitro-p-pheny lenediamine, Re/.s: l)Beil 16,(372) 2)G.T.Morgan & A.W.
 1

B 82

Upton,JCS 1 I 1, 195(1917) H4:N2; mw 240.22, N 23.33%; red trysts, with

4.Formylimino.l.diazonium*l, 4.benzoquinone a copper luster, mp expl violently at 60-65°;
[called Formyl-p-phenylenediazoimide by Morgan was prepd by ,diazotizing the hydrochloride of
& Upton(Ref 2) and Benzochinon-( 1.4)-formylimid 4-nitrophenyI-p-phenylene-diamine and pptg the
-diazid or N-Formyl-4-diazo-anilin in Ger(Ref 1)1, product by adding ammonia. The dry subst expl
0Hc.N:C6H4:N2+1 .5H20; mw 174.16, N 24.l~%; when rubbed
paIe yel trysts, very umstable, darkens even in R efs: l)Beil 16,603 2)G.T.Morgan & M.G.
absence of light and evoIves N2 at RT; mp expl Micklethwait,JCS 93 1,611(1908)
ca 12 5-8°; was prepd by adding N-formyl-p-phenyl- 4.(2’,4’.Dinitro.phenylimine).1.diazonium.l,4
enediamine to a soln of nitrous anhydride in cool- .benzoquinone
2 ,4-Dinitroph
called enyl-p-phenyl-
ed, dry aceG cooled dry eth was added to sepa- enediazoimine by Morgan & MickIethwait(Ref 2)
rate the prod and p-Chinon-(2.4-dinitro-anil)-diazid or 2‘.4’-Di-
Re/s: l)Beil 16,(371) 2)G.T.Morgin & A. W. Up-
nitro-4-diazo-dipheny Iamin in Ger(R ef 1)], (02N ~
ton,JCS 111, 190-3(1917)
C6H~.N:C6H4:Nz;mw 285.22, N 24.56%; red tryst,
4.Phenylimino.l.diazonium.l,4.benzoquinone(cal-
darken on exposure to Iight, mp expl on heating
led p-Chinon-anil-diazid or 4-Diazo-diphenylamin
ca 110-115°; S1 sol in aIc; sol in benz with some
in Ger), CeH~.N!C6H4:N2; mw 195.22, N 21.53?4;
decompn; was prepd by adding K bicarbonate to
bm-yel trysts, mp expl moderately on heating; SI
an aq soln of 2,4-dinitrophenyl-paminobenzene-
sol in chlf or acet, giving a brn-colored soln; in-
diazonium chloride, previously obtd by diazotiz-
SOI in w; was first obtd in an impure state as a
ing the hydrochloride of 2,4-dinitrophenyl-p-phen-
bm substance by Ikuta (Ref 2) and prepd in a pure
state by Hantzsch(Ref 3) by treating a cooled aq ylenediamine
suspension of diphenylamine-4-diazonium sulfate Refs: l)BeiI 16,603 2)G.T.Morgan & M. G. Mickle-
with ammonia. The constitution and structure of thwait,JCS 93 1,610(1908)
this class of compds have been discussed by 4.(2’,4’,6’.Trinitrophenylimino).1.diazonium.l,4
Morgan & Micklethwait(Ref 4) and by Morgan & .benzoquinone [called 2,4,6-Trinitropheny l-p
Read(R’ef 5) -phenylenediazoimine by Morgan & Micklethwait
R efs: l)BeiI 16,603 2)M.Ikuta,Ann 203,282 (Ref 2) and p-Chinon-(2.4.6-trinitro-anil-diazid
(1888) 3)A.Hantzsch,Ber 35,895(1905) 4)G.T. or 2‘. 4‘. 6’-Trinitro-4-di azo-diphenylamin in Ger.
Morgan & M. G. Micklethwait,JCS 93,605-8(1908) (Ref I)], (02 N)~C6H2.N:CeH4:N2; mw 330.22,
5)G.T.Morgan & H.N.Read,JCS 12111,2710-11 N 25.45%; brn-red, diamond-shaped crysts(from
(1922) benz+petr eth), mp expl ca 120-130°; was obtd
4.(2’.Nitro.phenylimine).l.diazonium.l,4.benz. by filtering a freshly prepd diazotized soln of
quinone [c@led 2-Nitrophenyl-p-phenylenediazo- 2,4,6-trinitrophenyl-p-phenylenedi amine(picryl-p
imine by Morgan & Micklethwait(Ref 2) and p -phenylenediamine) into aq Na acetate. On ex-
-Chinon-(2-nitro-anil)-diazid or 2’-N’itro-4-diazo pln, the prod emits clouds of black smoke
-diphenyIamin in Ger(Ref I)], 0zN.C6H4.N:C6- Refs: l)Beil 16,603 2)G.T.Morgan & M.G.
H4:N2; mw 240.22, N 23.33%; scarlet amor ppt, Micklethwait,JCS 93 1,609(1908)
darkens at 30°; mp expl at 85-90°; was prepd by Benzoquinone.1,4.azine (called P-Chinon-azin in
diazotizing the hydrochloride of 2-nitrophenyl-p Ger), 0:c6H4:N.N:C6H4:O; mw 212.20, N 13.20%;
-phenylenediamine and pptg the prod by adding trysts from org solns in two modifns: as dk orn
well-cooled ammonia to its Na acetate soln. The -red prisms or ndIs, mp 2-3° and as dk-yel
dry substance is extremeIy unstable, dec at RT rhombohedtal Ifts or plates, mp 42°; both modifns
and expl when gently rubbed on a hard surface have a blue reflex; on heating to higher temps, the
Re/s: l)Beil 16,603 2)G.T.Morgan & M. G. Mickle- color darkens and the trysts expl at ca 185°;
thwait,JCS 93 1,612(1908) readily sol in benz, chlf, hot abs ale, hot et acet,
44’*Nitro.pheny limine~ l*diazonium* l,4*benz~ hot acet or hot glac AcOH; diffc SOI in eth or in
quinone [called 4-Nitrophenyl-p-phenylenediazo- boiIing w; almost insol in petr eth; was prepd by
imide by Morgan & Micklethwait(Ref 2) and p shaking an ethereal soln of p-azophenol with
-Chinon-(4-nitro-anil)-diazid or 4’-Nitro-4-diazo silver oxide and fused Na sulfate(Ref 2). Other
-diphenylamin in Ger(Ref I)], 0.#.C6H4.N:C6- props and methods of prepn are given in Refs 1
&3

I
 B 83

Refs: l)Beil 7,628,(345) & [576] 2)R.Willstatter & Refs: l)Beil 7,621,(344) & [5741 2)A.Krause,
H. M. Benz,Ber 39,3486(1906) & JCS 90 1,997(1906) Ber 12,47(1879) 3) A. Knorr, Ber 43,799(1910)
3)L.Hunter & S. Barnes, JCS 1928,2055 Benzoquinone.l,4.di(methyli mine), CH3N:C#4-
Benzoquinonediimine and Derivatives :N.CH3; mw 134.18, N 20.88%; wh trysts, mp ca
Benzoquinone-1,4-diimine[called Benzochinon 92.5-93°, giving a red liq; readily sol in chlf, eth
-(1 .4)-diimid; p-Chinondiimid or Chinondiimid in or benz(giving a yel soln); sol in excess w or
aIc; rapidly decomps in solns, separating a dk
Ger], HN:C6H4 :NH; mw 106.12, N 26.40%;
It-yel ndls, becoming brn-yel or gray on product; expl on contact with HCI or H2S04; was
standing in air; mp ca 124° (begins to prepd by heating a soln of sym-dimethyl-p-phenyl-
darken at ca 75° ); expl when heated rapidly enediamine in gasoline with lead peroxide(Refs
above mp; readily SOI in warm et acet; sol in chlf 1&2)
or boiling benz; diffc sol in petr eth; expl when Re/s: l)Beil 7,621 2)R.Willstatter & A. Pfannen-
brought into contact with coned hydrochloric or stiel,Ber 38,2249(1905)
sulfuric acid; was prepd by Will stStter & Mayer Benzoquinone-1 .imino-4-methylimine, CH3 .N:C6-
(Ref 2) by treating an ethereal suspension of the H4:NH; mw 120.15, N 23.32%; COI prisms, mp 64
dichlorohydrate of benzoquinone-1,4-dichIoro- -7°, very unstable. compd, dec on standing in fess
imine, C6H4N2C12.2HC1, with ammonia gas, Its than 1 hr, becoming a brn tarry product. Other
Perchlorate salt, C6H6N2+2HC104 (?), wh trysts, props & prepn are given in Refs 1 & 2
mp expl violently on heating; in the presence of Re/s: l)Beil 7,620 2)R.Willst?Nter & C. W. Moore,
moisture, color changes to blue-grn, violet and Ber 40,2671(1907)
then to brn; was prepd by Hofman et almef 3) by Benzoquinone-1-imino-4 -dim etbylammonium hy-
the interaction of benzoquinone-1,4-diimine and droxide [called Benzochinon-( l,4)-imid-dimethyl-
perchloric acid immoniumhydroxyd in Ger], HO-(CH9 )2 N:C6H4 :N~
Re/s: l)Beil 7,620,(344) & [574] 2)R.Willststter & mw 152.19, N 18.41%. Obtd as the Dinitrate salt,
E. Mayer,Ber 37,1499 & 1501(1904) 3)K.A.Hofmann 03 N.(CHa)2N:C6H4: NH. HN03~ yel prisms, dec
et al,Ber 43,180(1910) on storage, mp expl on heating; sol in W, giving
Benzoquinone-1,4.di(bromo.imine), BrN:C6H :NBG
a dk-red soln; was prepd by passing N oxides in-
mw 263.94, N 10.62%; trysts, mp expl ca 86 8 ;
to an alc soln of asym-dimethyl-p-pheny lenedi-
was claimed to have been prepd by Krause(Ref 2)
amine and nitric acid
by treating an aq soIn of p-phenyIenediamine
Re/s: l)Beil 7,621 2)R.Willst~tter & J. Piccard,
chloride with an excess of bromine water. No an-
Ber 41,1473(1908)& JCS 94 I, 476(1908)
analysis of the compd was given
2,3,5. Trinitrobenzoquinone.l.imino.4(?)*trimethyl*
Re/s: l)Beil- not found 2)A.Krause,Ber 12,50
imine [calIed 2,3,5-Trinitro-benzochinon-(1.4)
( 1879)
-imid-( 1)-trimethylimid-(4)(? ) in Gerl, (CH~)aN:Cg
Benzoquinon-l,4.di(chloro.imine) [called Eenzo-
H4(N02)3:NH(?); mw 285.22, N 24.56%; golden
Chinon-( 1.4)-bis-chlorimid or p-Chinon-bis-chlor-
-Yel scales, mp dec at 200-2200; insol in w or alc
imid in Ger], CIN:C6H4:NCI; mw 175.02, N 16.0 U%;
soln in HC1 is colorless; dec on heating the acid
ndls(from w) having a SI aromatic odor, mp 124
soln near boiling; was prepd from trirnethyl-(4-
-6°(dec); expl when heated rapidly above the mp;
-acetylaminophe nyl)-ammoniurn nitrate by nitra-
readily sol in hot SIC, hot AcOH, eth or benz; S1
tion with fuming nitric and coned sulfuric acids.
sol in hot w; almost insol in cold w; was first
The prod is unstable
prepd by Krause(Ref 2) by treating an ice-cold
Refs: l)Beil 7,(350) 2)R.Meldola & W. R. Hollely,
soln of p-phenylenediamine in dil HCI with, an ex-
JCS 107 1,621(1915)
cess of chlorinated Iime(bleaching powder).
Other props & methods of prepn are given in Ref Benzoquinonedioxime and Derivatives
1. It forms addn compds, some of which are expl:
Benzoquinone-1,4-dioxime [calIed Benzochinon
Benzidine Compound, C6H4N2C12+2(C1 *H12N2),
-(1 .4)-dioxim or p-Chinondioxim in Ger], HO. N:-
violet crpts(from benz), mp expl mildly at ca C6H4 :N.OH; mw 138.12, N 20.28%; It gray gran-
121°(Ref 3); Hydroquinone Compoundt ular crysts(from boiling w) or It yel ndls(hydrate),
C6~N2C12+C6He02, dk-grn ndls, mp expl Ca mp 240 °(dec); sol in coned NH40H; S1 sol in w;
129-130°, dec on warming with w or benz(Ref 3) v SI sol in dil q NH40H; was first prepd by
 B 84

Nietzki & Kehrmann(Ref 2) by various methods. higher temps; very sol in eth, chlf or hot ale; in-
Other props and methods of prepn are given in SO1 in w or dil acids; dissolves w/o decompn in
Ref 1. Benzoquinone-l,4-dioxime forms interest- cold coned H2S04 or fuming HN03. Other
ing derivs, some of which are expl(see below). props & methods of prepn are given in Ref 1.
Jerczak & Fettes(Ref 3) proposed its use in the Its addn compd with hydroquinone, C6H4NOCI+
“vulcanization” or ‘curing’ of rubberlike poly- C6HG02, bl-grn trysts with a metalIic Iuster, mp
meric substs expl at ca 119°, dec on heating with w or benz,
Re/s: l)Beil 7,627& [576] 2)R.Nietzki & F. was prepd by Knorr(Ref 2)
Kehrmann,Ber 20,614(1887) 3)J.S.Jerczak & E. Re/s: l)Beil 7,619,(344) & [574] 2)A.Knorr,Ber
M. Fettes,IEC 43,326(1951) 43,799(1910)
Benzoquinone.l,4.dioxime,Oxidation Product [caI- Benzoquinone.1,4.monocyanhydrin [called p-Chin-
led “p-DinitrosobenzaI” by Nietzki & Kehrmann on-mono-cyanhydraxon, Benzochinon-( 1.4)-mono
(Ref 2) and called “p-Benzoquinone$ioxime Per- -cyanhydrazon or p-Oxy-benzolazof ormonitril in
oxide” by Forster & Barker(Ref 3)] ,0~H~:~~6, Ger], NC. HN.N:C6H4:O; mw 147. L3, N 28.56$%;
mw 136.11, N 20.58!%; goIden-yel ppt, mp dec with yel ndls(from alc+w), mp expl ca 117- 118°; read-
mild expln when heated rapidly; very sl sol in ily sol in eth or ale; was prepd from p-hydroxy-
common org SOIVS; was prepd by the oxidn of benzenediazonium chloride and coned KCN soln,
benzoquinone-1 ,4-dioxime in alk soln with K ferri- dissolving the resulting compd in w and pptg the
cyanide(Ref 2) and by the action of hydrazine product with HC1
hydrate in boiling alc soln on p-phenylenediamine Re/s: l)Beil 7,629 & [577] 2)A.R.Hantzsch & W.
(Ref 3) B.Davidson,Ber n, 1532(1896) & JCS 70 I?541
Re/s: l)Beil 7,628 & (345) 2)R.Nietzki & F. , , (1896)
Kehrmann,Ber20,615( 1887) & JCS ~ 1,575( 1887) 2.Azid.6.nitro.4trimethylammonium.l,4benzo
3)M.O.Forster & M. F. Barker,JCS 103 11,1922(1913) quinone[called 2-Nitro-6-triazo-4-trimethylam-
Benzoquinone. 1,4.dioxime Polymers of the An. monium-l-benzoquinone by Meldolq ~ Hollely
hydride[calIed Polymeres-p*Chinon-dioximanhy- (Ref 2) and called 6-Nitro-2-azido-benzochinon
drid in Ger], ~01 ; mw (120.11 )X, N -(1.4 )-trimethylimid-(4) in Ger],
(N: C6H4:N)X ,CH=C(N02 )\
(23.33)X %; it-red amor subst, mp expl violently (CH3 )3N:C C:O; mw 237.22, N
when heated above 300°; insol in all known solvq “CH=C(N3 )/
was obtd by allowing the aq soIn of the Na salt 29.53%; red ndls or red scales(from w), mp- be-
to stand. The prod is very unstable in storage comes dk-brn at 100° and expl; was prepd from
Refs: l)BeiI 7,628 2)R.C.Farmer & A. Hantzsch, 2 ,6-dinitro-4-trimethyl ammonium- l-benzoquinone
by reducing it with ammonium sulfide, converting
Ber 32,3107(1899)& JCS 78 1,103(1900)
the nitro-amino compd into a chloride, diazotiz-
Benzoquinoneimine and Derivatives ing the product and treating it with Na azide.
Benzoquinone-1,4-monoimine [called Benzochinon This compd is distinctly basic and its salts with
-(1 .4)-monoimid; p-Chinon-monoimid or p-Chinon - mineral acids are colorless
imid in Ger], HN:C6H4:O; mw 107.11, N 13.08%; Re/s: l)Beil 13,(198) 2)R.Meldola & W. F. Hollely
lt sulfur-yel trysts, mp expl mildly on heating; JCS 105 1,1477(1914)
2,6.Diazido.4.trimethylammonium.l,4.benzoquinone
unstable in the dry state; readily sol in eth or
[caIled 2,6-Bistriazo-4-trimethylammonium-l-benze
benz; mod sol in CS2; other props & prepn are
quinone by Meldola & Hollely(Ref 2) and called 2
given in Refs
-6-Diazido-benzochinon-( 1.4)-trimethylimid-(4) in
Re/s: l)BeiI 7,619 & [574] 2)R.WiIlst~tter & A.
Ger], ,CH=C(N3 ),
Pfannenstiel,Ber 37,46o7( 1904) 3)F.Kehtmann,
(C% )3N:C, C:O; mw 233.23, N
Ber 56,2399(1923)
CH=C(N3)’
Benzoquinones.l,4.monochloroimine [called Benzo-
42.04%; brn subst, mp expl ca 100°; very SOI in
chinon-( 1.4)-mono-chlorimid; p-Chinon-monochlor
w; decomp in boiling w; was prepd by reducing
imid or Chinonchlorimid in Ger], CI.N:C6H4:O;
the dinitro-compd with tin and HCI, diazotizing
mw 141.52, N 9.90%; yel ndIs(from gasoIine or
the product and treating it with Na azide. The
glac A cOH), mp 85°(partially sublimes), expl at
compd was not obtd in a pure state but its salts
 B 85

were sufficiently definite to establish its constit- Silv e? salt, AgC6H4N02, almost black, but dk
ution. Chloride salt, C9H1 ,N70+HC1, CO1 ndls, blue in transmitted light, fine trysts, expl on
becoming brn on exposure to air, mp expl ca 100°; heating or on contact with acids; Sodium salt,,
dec in w or ale; Picrate salt, C9H21N70+C6H3- NaC6H4N02, red-grn shiny Ifts, expl on heating
N307, yel scale s(from ale), mp very expl cdmpd, Benzoquinone. 1, 4-mono6xime [called Benz~
its melting or decompg point could not be detd
chinon-(1.4)-monoxim; p-C!hinon-monoxim or ‘p
Re/s: i)Beil 13,(198) 2)R.Meldola & W. F. Hoi- ,CH=CH,
-Nitroso-phenol” in Ger],
lely,JCS 105 I, 1478-80(1914) HON:C C:o
4,6.Dinitro.l,2.benzoquinone.2.chlorimine[called “CH=CHZ
3,5-Dinitro-benzochinon-(1.2)-chlorimid-(1) in Ger] ,CH=CH,
,CH=C(N02), or ON.C .
\
CH-CHZC . OH ; almost COI ndls(by rapid
(OZN)CNCH.C(:NC1) ,C:O; mw 231.56, N 18,14%;
cooling from boiling w) or yel-wh ndls(from acet+
yel pcfr, mp expl; readily sol in acet; sol in meth- benz), mp 133°(dec); other props and methods of
anol, alc or glac AcOH; SI sol in benz, eth or
prepn are given in Ref 2. It forms numerous salts,
xylol; diffc sol in cold w; partially decompg in
some of which undoubtedly are expl
boiling w; was obtd, in an impute state, by treat-
Re/s: l)Beil 7,600,(337) & [566] 2)Beil 7,622,
ing a soln of picramic acid, in the presence of
(344) & [ 5741
HCI, with cold chlorine water, The expl props of Benzoquinone.1.(.chloroethylimine).4.oxime [cd-
this compd were not investigated
led p<hinon-(~ -chlor-~thylimid)-oxim in Ger],
Re/s: l)Beil 7,[ 567] 2)S.Blaszkovska, BullInter-
AcadPolonaise 9-1 OA,4O9(1924);JCS 128 II, 1043 H0.N:C6H~:N.CH2 -CH2.Cl; mw 184.63, N 15.18%;

( 1925)&CA 20,1552(1926) dk-gm, steel-blue, iridescent scales(from benz+

ligroin), mp ca 90°, dec with expln ca 120°; obtd
Benzoquinone.l.imino.4.diazonium Salts. The by reacting aq Na nitrite with (~ -chloroetbyl)
expl salts Hydrochloride, Chromate, and Picrate -aniline and treating the nitroso-deriv with alc
are described in Vol 1 of this Encyclopedia under HCI
Refs: l)Beil 7,[576] 2)G.R.Clemo & W.H. Perkin,
l.Aminobenzene.4.diazonium Hydroxide or ,Anilino
Jr,JCS 125 II, 1810(1924)
.4.diazonium Hydroxide. These salts were origin-
Benzoquinone.l.4.monooxime Hypochlorite, CIO-
ally considered to be derivs of the hypothetical
.N:Ce H4:O; mw 157.56, N 8.93%; yel ndls, very
hydroxide, H2N.C6H4 .N(~N).OH, as parent compd
unstable, evolving HOCI when exposed to light:
(Refs 1 & 2). Gray(Ref 3) claims that these salts
mp expl on heating to ca 70° or on contact with
possess a quinoid structure and are not derivs of
coned H2S06; readily sol in ale, eth, chlf or
aminobenzene diazonium hydroxide but salts of
l-imino-4-cIiazido-benzoquinone benz; in=ol in w; was prepd by treating an aq soln
of benzoquinone- 1,4-mono~xime with HCI and
R e/s: l)Beil 16,602 & [306] 2)R.Meldola & L.
Eynon,JCS 87 1,2(1905) 3)w’.H.Gray,JCS 1~26, bleaching pdr until a distinct odor of hypochlo-
rous acid,HOCl was observed
3174-3179
Re/s: l)Beil 7,625 2)R,M~hlau,Ber 19,281(1886)
Benzoquinonemonooxime and Derivatives & JCS 50 1,453(1886)
Benzoquinonemonooxime, C6H5N02; mw 123.11, Benzoquinone.1.semicarbazone.4.oxime, HO.N:-
N 11.38%. This compd exists as ortho and pata CGH4:N.NH.C0.NHZ; mw 180.17, N 31. 10z; brn
isomers: B enzoquirzone- 1,2-mono~xime [called -Yel ndls(from ACOH & w), mp dec ca 238°, expl
Benzochinon-( 1. 2)-monoxim; o-Chinon-monoxim ca 247°; sol in glac ACOH; insol in w, alc or
or “o-Nitroso-phenol” in Ger], eth; was prepd from benzoquinone- 1$4-mono~xime
.CH====CH,
HC” t:o and the hydrochloride of semicarbazide in alc
,CH-CH\ soln
‘CH-C(:NOH)’
or HC C. OH; Refs: l)Beil 7,630 2)J.Thiele & W. Barlow, Ann
‘CH-C(NO)4
302,331( 1898) 3)W.Borsche & A. Reclaire,Ber 40,
dk grn-yel ndls(from petr eth), mp 142°(dec); other
3806( 1907)
props and methods of prepn ate given in Ref 1.
3.Brom.l,4.benzoquinone.1.methylimine.4.oxime,
It forms numerous saits, some of which ate expl:
 :

B 86

H0.N:C6H3(Br):N. CH~; mw 251.07, N 13.03%; grn Re/s: l)Beil 14, [153] 2)G.Heller et al,Ber 56,
ctysts, mp darkens ca 100° and expl ca 124°; was 1870(1923)& JCS 124 1,1095(1923)
obtd by hydrolysis of the hydrochloride of methyl
Benzatetrazolecarboxylic Acid. A misnomer for
(Ybromophenyl)-nitrosoamine. The HC1 salt chang.
1,2,3 -Triazapyrrocoline-6-carboxylic Acid
ed from pink to yel at 140° and melted ca 168°
Refs: l)Beil 7,[583] 2)M.S.Kharasch & J.F. Benzotoluide and Derivatives
Piccard,JACS 42,1859(1920)
Benzotoluide or BenzometbyIanilide (called Benzoe-
2,6@ibrome 1,4*benzoquinonea4*oxime,
sauretoluidid, in Ger), Cel$ .C0.NH.C~H4.CH3.
H0.N:CGH2(Br)2 :0; mw 280.92, N 4.99%; brn
ndls(from toluene, alc or AcOH) or Ifts(from diI Three isomers are described in Beil 12,795,861,
ale); mp darkens ca 160° and detonates betw 168 926,(380,400,421) & [505]. The para isomer is
& 175°; readily sol in alc or eth; SOI in chlf or probably of most interest since its tetranitro deriv
glac AcOH; S1 sol in w; other props and methods has been prepd
of prepn are given in Ref 1 Mono-, Di- and Trinitrobenzotoluides. Several
Re/s: l)Beil 7,641 2)F.Kehrmann, Ber 2i~318 isomers are described in Beil 12 and in Rec 55,
(1888) 2536(1936). None of these is expl
6.Nitro.3.hydroxy.l,2.benzoquinone2.0xime.4 Tetranitrobenzotoluide, C14H,N, 0, mw 391.25, N 17. 90%.
diozoniumhydroxide, One isomer, 3, 5-Dinitrobenz-2’, 6’-dinitromethyl-
,CH= C(N02 )\ anilide,(02N)2C=H3 .CO.NH. C6H2(N02)2.CH3;
HO(N:)N.C C:O; mw 228.12, paIe yel ndls(from AcOH), mp 275°, was prepd
‘C(OH}C( :NOH)’ by nitration of 3,5-dinitrobenz-4’-methylaniIide
N 24.56%; its chloride and some other derivs with abs nitric acid. Its expl props were not
were prepd by HelIer & Sourlis(Ref 2) who did investigated
not investigate their expl properties Re/s: l) Beil- not found 2)W. B.van Horssen,Rec
Re/.s: l)Beil 16,(367) 2)G.HeIler & A. Sourlis,Ber 55,255-6(1936) & CA 30,5199(1936)
43,2586-7(1910)
6.Nitro.4.nitrosoamo.3.hydroxy.1,2.benzoquinone Benzotriazine and Derivatives
.2.oxime, ,CH- C(N02 )\ Benzotriazine, C7H5N3; mw 131.13, N 32.05%.
ON. HN.C<C(OH).C( :NOH) ,C:O; mw The 1, 2,3(or vie)-isomer, H = CH-$.N--N;
H z = CH–C=CH-I!
228.12, N 24.56%; dk-yel plates(from acet+w) or seems to exist in the form of derivs, whiIe the
crysts(from w), mp expl violently on heating; l,2,4(or as)-isomer, H$CH-C.N-IN,
readily sol in glac AcOH; mod sol in ale; sl sol HC=CH-+=N-CH
in benz, chlf or Iigroin; was prepd from aq 6-nitro exists as a yel solid, mp 74-5°, Other props &
-4-aminoresorcinol hydrochloride or hydrobromide prepn are given in Beil 26, 67,( 15) & [33]
and 2 mols of Na nitrite in acid soln at OO. Its (Benzo.l,2,3.triazine).3.oxide or Benzo.3.oxy.vic
Na & K acetate solns have a dark-grn coIor; the .triazine, C7HSN30; yel ndls, mp 160-160 .5°(decJ
trysts of these salts sometimes expI by only rub- Its 6,8-dibromo-deriv, called “Dibromindiazonoxim”
bing with a glass rod under water by Bamberger, yel ndls(from benz) expI ca 182°.
Refs: l)Beil 14,(494) 2)G.Heller & A. SourIis, It was prepd by treating 2-amino-3, 5-dibromobenz-
Ber 43,2585(1910)& ]CS 98 1,749(191 O) aldoxime with NaN02 in ACOH soln
4.Nitro.6.nitrosoamino.5.hydroxy.1,2..benzoquia Re/s: l)Beil 26,67 2)E.Bamberger & E.Demuth,
none.2.oxime, ,C(OH)=C(NH.NO), Ber 34,1327-8(1901)
02N.C C:o; (Benz~l,2,3~triazine)40x ide or Benzrw4*oxywic
>CH
—----C(:NOH)’ l triazine (called 4-Oxy-benzo- l.2.3-triazin in Ger;
mw 2?8. 12, N 24.56%; small yel hex rods(from former name “Benzazimid”), H$=CH-$~ ;
acet+petr eth), mp expl on heating; readily sol in HC=CH-C-CO-NH
alc or acet; diffc sol in benz, chlf or petr eth; mw 147.13, N 28.56%. Its other form,
dec by boiling in water; was prepd from aq 4-nitro H$=CH+N ~~;which may be called B enzo-
-2-aminoresorcinol and 2 mols of NaN02 in H2- HC= CH- C-C(OH)=N
S04 soln .4-by droxy-uic-triazine, was prepd by several in-

1
vestigators using different methods, as crys~s de- & CA 50,12481(1956) 9)Sax(1957),p 350
compg ca 211-13° and explg when tested in a Mononitroknzotriazole, C6H4N402; mw 164.12,
flame N 34. 14%. The following isomers are described
It forms salts, some of which are expl, such as in the literature: 5 (or 6)-iVitrobenzotn”azole, ndls,
Silver salt, AgC7H4N30, wh amorph ppt, explg on mp 209-110 (Ref 1), mp 215-6°(Ref 3), its Silver
heating. Sodium salt, It yel lfts, explg on heating salt is a mild expl(Ref 1); 4(or7)-iVitrob enzotri-
or on contact with coned H2S04 ~~~j~v~ts, dec ca 230 °(Ref 2); mp 236-237.3°
R efs: l)Beil 26,163-4 & [88] 2)A.Weddige & H.
Finger, JPraktChem 35,262-4( 1887) 3)H.Fi%er> Re/s: l)Beil 26,43 2)Beil 26,( 10) 3)N.L.Miller
Ibid 37,432-4( 1888) 4)E.Zacharias,Ibid 43,446 & E. C. Wagner,JACS 76, 1850-1(1954)
( 1891) 5)A.Reissert & F. Grube,Ber 42,3721(1909) Dinitrobenzotriazole CeHaN~04; mw 209.12, N,
6)G.Heller & A. Siller,JPraktChem 116, 9 & 14 33.49%. The following isomer is described in the
( 1927) literature: 2,4-Dinitrobenzo - a - vic-triazole,
6.Nitrobenzo.4.oxy.vic.triazine (called m-Nitro- 02N. =C d-NH,
benzazimid H$=CH-C-N=N
by Kratz), ; H z .C(N02)4_N-N; CO1 ndls(from dil alc),
02N.&cH-~CO-~H mp 198°. Can be prepd by treating 3, 5-dinitro -
mw 192.13, N 29.16%; lt yel ifts(from dil ale),
phenylenediamine with Na nitrite in aq acid. Its
dec 185° and expl when heated on Pt foil in a
expl props were not investigated
flame. Was prepd by treating 5-nitro-2-aminO-benz-
Re/s: l)Beil 26,50 2)R.Nietzki & H. Hagenbach,
amide with K nitrite in dil AcOH under cooling
Ber 30,543(1897)
Forms salts, some of them expl, such as So.
Trinitrobenzotriazole, C6H2N606- not found in
dium salt, NaC7H3N403, It yel ndls(from a~c+
Beil or in CA through 1956
eth), expl on heating
Refs: l)Beil 26,166 2)K.Kratz,JPraktChem 53, Benzotriazolol and Derivatives
2 13( 1896)
B enzotrr”azolol, Hydroxybenzotriazole, Benzo-
l,2,3,Benzotriazino. 3,4.a] perimidine. See o
hydroxyttiazole or B enzazimidol (Called @ybenz-
-Amidophenylperimidine,Vol l,p A 246-L
triazol in Ger), C6HsN~O; mw 135.12, N 13.10%.
Benzotriazole and Derivatives
The following isomer is described in the literature :
Benzotriazole (formerly called Aziminoberzzol and Benzotriazol. I-ol or (Benzo-1-bydroxy) -a -vic-tri-

Pbentriazol in Ger), C6H5N3; mw 119.12, N35.28%;

azole (called l-Oxy-benztriazol; Benzazimidol
CO1 ndls, mp 95-1000. Two forms are possible: or Benzolazimidol in Ger), H? CH-~-N(C)H)
‘N;
Benzo-a-v(or 1,2,3 )-triazole, ‘~=cH-~-NH\N HC=CH-C-N~”
HC=CH–C—N< ndls, mp 157°. Other props & prepn are given in
and Benzo-fl-v (2,3, 1)-triazole, H~= CH-C=N1 the Refs. Its Lead salt, Pb(C6H4NaO)2, lfts,
NH
HC= CH- L =N’ expl ca 270°
(Ref 1).Many methods of prepn are known, of which Re/s: l)Beil 26,41 2)R.Nietzki & E. Braunsch-
the treatment of p-phenylenediamine with Na ni- weig,Ber 27,3381 -w(1894) 3)T.Zincke & P.
trite in dil AcOH is described in detail in Ref 6. Schwarz,Ann 3 11,332(1900)
It is not recommended to prep large batches be- Benzotriazol-4-ol or (Benzo-4-bydroxy) -a- vie. tri-
cause of the possibility of accidental expln dur- azole, HC. CH~-NHx
N; which may be con-
ing vacuum distn of benzotriazole. One such expln H/= C(OH)-C-N ~
took place in 1956 at the Maumee Chemical Plant, sidered as a parent compd of 6-mononitro-benzo
Toledo, Ohio(Ref 8) -triazol-4-ol described below, could not be found
Nitration of benzotriazole is described in Ref 5
in BeiI
and its toxicity and hazard in Ref 9
5.Monochlor.benzotriazol.l.ol; (5 -Cblorobenzo
Refs: l)Beil 26,38 & [17] 2)A.Ladenburg,Ber 9,
- I-hydroxy)- a -vie-triazole or .5-Cbloro-benzazi-
222(1875) 3)T.Zincke et al, Ann 291,320(1896)
midol, C6H4N30CI; Ifts(from dil ale), deflgr at
4)K.Elbs,JPraktChem 108,213(1924) 5)K.Fries
et al, Ann 511 ,229(1934) 6) OrgSynth 20,5(1940) 204-5°. Can be prepd by heating 2,4-dichloro
7)N.L.Miller & E. C. Wagner,JACS 76, 1850-1(1954) - l-nitrobenzene with an excess of hydrazine-
& CA 49,8264(1955) 8)Anon,C&EN 34,2450( 1956) hydtate in ale. Its Potassium salt, KC~H3N~OCl,
 I

B 88

Ifts(from ale), deflgr above 300° 8738-9(1953)

Re/s: l)Beil 26, [24-5] 2) E. M~ller & G. Zimmer- 4.Mononitro.benztriazol.I.ol; 4-Nitroben zo-l-hydr-
mann, JPraktChem 1 I 1,279 & 285-6( 1925) oxy-a-vic-triazole or 4- Nitrobenzazimidol,
HC=~H— C-N~OH) ; mw 180.12, N 31.11%;
6.MonochIor-benzotriazol.1.ol; (6- Cldombenzo
HGC(N02)-/–@
- l-hydroxy)-a-vic- tn”azole, or 6- Cbloro-benzazim- orn trysts of the monohydrate lose w ca 140° and
idole; col ndls(from dil ale), mp dec ca 195° and deflgr ca 229° with evoln of flame and smoke;
expl when heated at higher temp; can be prepd
easily sol in dil ale; diffc SOI in w. Can be prepd
by treating 2,5-dichloro- l-nitrobenzene with an
by treating 2,6-dinitrophenylhydrazone” with cold
excess of hydrazinehydrate in ale. Its Silver salt,
NaOH soIn or warm ammonia
AgC6H~ N30C1, expl when heated on a Pt foil in
Re/s: l)BeiI 26,(11) 2)W.Borsche & D. Rantschefi
a flame Ann 379,172(1911)
Refs: l)Beil 26,[25] 2) J.Booy & J. W. Dienske,. 6.Mononitro.benzotriazol.1.ol; (6-Nitrojenzo.l
Rec 45,449( 1926) -bydroxy)-a-vic- triazole or 6-Nitro-benzazimidoI,
5,6.Dichloro.benzotriazol.I.oI; 5, 6- Dicblorobenz-
mw 180.12, N 3 L 11%, yel trysts, mp deflgr 190-2°
azirnidol or l-bydroxy-j, 6-dicbIoro-a(or IH). benzo- (Ref 2), dec explosively 206°(Refs 3 & 4); sol in
trr”azole, Cl.= CH-$–N(OH)-~ mw 204.02, N hot w, hot alc or hot NB; insol in eth, kigroin or
Cl,~=CH–C N benz. Can be prepd by heating 4-chloro- 1,3-dinitro -
20.60%; ndls(from ale), mp expl mildly ca 194-6°; benzene with hydrazine hydrate in alc(Ref 4) or by
readily sol in ale, glac AcOH acet or nitrobenz; other method s(Refs 1,2 & 3). Forms many salts,
nearly insol in eth, benz or Iigroin. It can be some of them expl, such as: Potassium salt, KC6-
prepd by treating 2,4, 5-trichloro-l-nitrobenzene H3N403, orn-yel trysts, dec explosively on heat-
or 4,5-dichloro-2-nitro-phenylhydrazine with hy- ing; Sodium salt, NaC6H3N403, red ndls, dec expl
drazine hydrate in alc soln. The Hydrazine salt, on heating(Ref 2} Hydrazine salt, C6H4N403 .N2
C6H3N30C12+N2H4, ndls(from ale), mp 205°(dec); H4, yel ndls (from ale), dec at 205-6°
Potassium salt, KC6H2N30, Ifts(from ale), mp Re/s: l)Beil 26,48 & [26] 2)T.Curtius,JPrakt-
expl betw 230° and 250°; Silver salt, AgC6H2N3- Chem 76, 374 & 383-5(1907) 3)L.SPiegel!Ber
0C12, ppt, sensitive to light; mp expl on heating; 41,886(1908) 4)0. L. Brady & J.N. EJ%,JCS
Barium BaC6HN30C12,
salt, ndls(from w), mp 123,2226(1923) 5)M.Tomita & K. Ikawa,Jpharm-
expl mildly on heating or on contact with H2S04; SocJapan, 75,457(1955)& CA 50,2480(1956)
Aniline salt, C6H3N30C12+C6H7N, ndls(from Chem 76,374 & 383-5(1907) 3)M.Tomita & K.
methanol), mp 168°(dec) and other salts are de- Ikawa,JPharmSocJ apan, 75,457( 1955) & CA 50,
scribed in the literature 2480(1956)
Re/s: l)Beil 26, [25] 2) E. M~ller & W. Hoffmann, (6Mononitro*&acetic acid)*benzotriazol~ l~ol or
JPraktChem 11 1,294,299,301(1925) 3)Compare, W. (6-Nitro-7 -acetic acid-1 -bydroxy)-1, 2,3(or a-vie)
Qvist,Acta Acad Aboensis,Math & Phys 19, No 4, - triazole[ called 6-Nitro-l-oxy-benztriazol-essig-
3-11 and No 5, 3-15(1953)& CA 49,89934(1955) s~ure-(5) in Ger], 02N. =CH-C-N(OH)-~,
(5,7.Dichlorobenzo.6.nitro).benzotriazoll.1.ol ol; HOOC.H2C. z = CH-~ N
~, 7-Dicbloro-6-nitrob enzazimidol or l-Hydroxy-5, mw 238.16, N 23.53%; yel Ifts(from w), mp dark-
7-dicbloro- 6-nitro-a(or lH)- benzotriazole, ens above 200°, expl ca 224°; was prepd by react-
02N.$=C(C1)-$N( OH)-N, mw 249.03, N 22.50%; ing 4 ,6-dinitro-3-hy drazino-phenylac etate with dil
CI,C=CH—C A NaOH soln
yel ndls(from ale), mp dec ca 196°; readily sol in Refs: l)Beil 26,[158] 2)W.Borsche,Ber 54,678
alc with partial decn. It can be prepd by treating (1921) & JCS 120 1,462(1921)
2,4,6 -trichloro- l,3-dinitrobenzene with an excess 6.Mononitro.benzotriazol.4.ol; (6-Nitrobenzo-4

of hydrazine hydrate in hot ale. The Hydrazine -bydroxy).a-vic. triazole or 6-Nitro-benzotriazol-4

salt, N2H4+C6H2N403C12, red-brn ndls(from ale), -01, 02N.=CH— –

N 31.11%
H~=C(OH)~_~_\N;mw 180.12,
mp- dec ca 169°; dec on prolonged standing in hot w
yel pdr, mp 197-8°; was prepd by refluxing for 6
Refs: l)Beil 26, [27] 2)W.Borsche & W. Trautner,
hrs 4-methoxy-6-nitrobenzotriazole with 48% HBr
Ann 447,6(1926) 3)Compare, S. S. Joshi & D.S.
soln. Its expl props were not investigated
Deorha,JIndianChemSoc 29,548( 1952) & CA 47,
 B 89

Refs: l)Beii-not found 2)H.B.Gillespie et al, ture, the ca~isomer, mp 127°(dec) and the /i?-isomer,
JACS 76,3532(1954) &CA 49,9633(1955) mp 187°(dec). The Silver salt of the a-isomer,
Note: No higher nitrated derivs of Benzotriazol- AK9H8N309, yel ppt, expl at ca 1300, while its
OIS were fo~nd in Beil or in CA rhtu 1956 petvxide, CGHS .CO(C2N202).N~, golden-yel sol-
id, dec ca 1450
Benzotrifluoride ond Derivatives
Re /s l)Beil 10,[ 566] 2)G.Ponzio & C. Cerrina,
Benzotri/!uoride or Pbenylfluomform (calIed 1’.- Gazz 58,29-31(1928)& CA 22,1971(1928)
1‘. 1‘-Trifluor- l-methyl-benzol and o .co.~-Trifluor
-toluoI in Ger), C6HS .CF3; CO1 Iiq, bp 103. ~ at Benzoylaminophenol. See Benzamidophenol
752mm. Other props & prepn are given in Beil 5,
290( 149) & [224] and its toxicity and hazard in Benzoylaniliine. See Benzanilide
%3X(1957),351
Mononitroberzzo tri/luoride, 02N.CeIi4.CF9. The Benzoylazide and Its Nitro Derivatives. See under
following isomers are described in the literature: Benzoic Acid
2-Nitro-, crysts(from de), mp 32.5 °(Ref 2)3.Nitroz
Benzoylazide Benzalhydrazone. See under Benzoic
COI liq, fr p -2.4°, bp 102-3° at 40mm; d 1.4318 at
Acid
18/4°, n~ 1.47418 at 18/4°, Q: 771. 3kcal/mol;
can be prepd by treating benzotrifluoride with
Benzoyl Azidodithiocorbonate. See Vol 1,p A633
fuming nitric acid(Ref 1) and 4-Nitro-, trysts, mp
-L
4L5°(Ref 2)
Refs: l)Beil 5,327,(162) & [2511 2)Beil 5,[251]
Benzoylazidomethone. See Acetophenone, Azido
Dinitrobenzotrifl uoride, (OZN),C,H,.CF,; mw 236.11
Derivatives; Vol I,p A47-R
N 11.86%. The 3,5 -Dinitro-isomer is described in
the literature. It consists of wh trysts, melting at Benzoylchloride and Derivatives
4950°; can be prepd by treating 3-nitrobenzotri- Benzoylcbloride or Benzoic Acid Chloride (called
fluoride with a mixt of fuming nitric acid(d 1.49 Benzoes~utechlorid in Ger), Ce H5 .COC1; mw 140.5
- L50) and oleum(20% free S03 ) at 95-100°. Its COI, pungent Iiq, d 1.212 at 20”/4°, mp -0.50, bp
expl props were investigated ca 1950 at PicArsn 197.2°, fl p 215°F(10L70) (closed cup); n~ 1.55-
and at the National Northern Cotp, but their re- 36 at 20°; very toxic. Can be prepd by interaction
sults are classified
of benzoic acid with sulfurylchloride or by other
Refs: l)Beil- not found 2)E.C.Finger et al,
methods. It is used in medicine, as a reagent and
TransIllinoisStateAcadSci 31, 132( 1939) & CA 33, as an intermediate in org reactions
6271(1939) 3)E.C.Finger & F.H.Reed,JACS 66, Re/s: l)Beil 9, 182,(94) & [ 159] 2)OrgSynth 24,
1973-4 ( 1944) 15( 1944) 3)CondChemDict( 1950),92 4)Sax( 1957),
35 I 5)US Specification MIL-B- 11346(Benzoyl
l,2,3.Benzoxadiazole. See Ben zenediazo~xide Chloride Reagent)
Mononitrobenzoy lcbloride, C7H4ClNO~. Three
2,l,3.Benzoxadiazote. See Benzofurazan
isomers: 2-,3- and 4-Nitrobenzoylchlorides are
described in Beil 9,373,381,394,(162) & [252,
Benzoylacetateperoxide. See Acetylbenzoylper- 270]
oxide; Vol l,p A55-L Dinitrobenzoylchloriole, C7H3C1N0205. The
following isomers are described in the Litera-
Benzoylacetylperoxide. See Acetylbenzoylperox- ture: 2,3-D initrobenzoylcb loride, oil(Ref 4,P
ide; VO1 l,P AN-R 3145, footnote); 2,4-Dinitrobenzoy lcbloride, ndls
(from petr eth), mp 42-6 °(Ref 1); 2,6. Dinitro-
Benzoyl Amide. See Benzamide benzoylcbloride, yel plate s(from eth), mp 96-8°
(Ref 2); 3,4-Dirzitroberzzoy lch20ride, (02N)2-
Benzoylaminoglyoxime or Aminobenzoylglyoxime, C6Ha.COCl; solid, mp 45-7 °(Ref 4); CO1 ndls
C6H~ .CO.C(:N.OH).C(:N. OH).NHZ; mw 171.16, N (from petr eth), mp 50-1°, bp 188° at llmm Hg,
24.55%. Two isomers are described in the litera- expl on heating above 225°, easily SOI in eth or
 I

B 90

benz; diffc sol in petr eth(Ref 5). Was first tendency to give ortho-substituted products(Refs
prepd in an impure state by treating 3,4-dinitr~ 3,4&5)
benzoic acid with P C15 (Ref 4). Goldstein & Re/s: l)Beil 9,181 2)F.E.Francis,JCS 891,1-4
Voegeli prepd it in a pure state by using thionyl ( 1906)& Ber 39,3798( 1906) 3)Sidgwick,0rgChem
chloride in lieu of PCl~ (Ref 5) and of N(1937), 11-12 4)Houben 4(1941),216 5)V.GOlq
3, J-Dinitmbenzoylchlotide, ndls(from benz), mp JCS 1950, 2467-73& CA 45,7537(1951) 6)H.
66-74°, bp 196° at 10-12 mm(Ref 3) Burton & P. F.G.Prail,JCS 1#55,729-31 & CA 50,
Re/s: l)Beil 9,412 2)Beil 9,413 3)Beil 9,414& 4820( 1956) (Investigation of acyI nitrates as a
[283] 4)L.C.Raiford & J. N.Wickert,JACS 53,3145 possible source of acylium ion, RCO+)
(1 931) 5)H.Goldstein & R.VoegeIi,Helv 26,477
3.Nitrobenzoyl Nitrate, 0#.C6H4 .C0.0.N02;
(1943) &CA 37, 57o9( 1943)
mw 212.12, trysts,
N 13.21%; mp 40-50°; expl
2,4,6.Trinitrobenzoylchloride, (02 N)3C6 H2.COCI;
on sudden heating; can be prepd by the action of
mw 275.57, N 15.25%; ndls(from benz or Iigroin),
Ag nitrate on 3-nitrobenzoyIchIoride at SI above
mp 130°(Ref 2); plates(from benz), mp 158°(Ref 31
35°
crysts(from benz by petr eth), mp 163° (Ref 4Y S1
Ref.s: l)Beil 9,381 2)F.E.Francis,Ber 39,38oO
sol in benz; diffc sol in eth; insol in Iigroin or
( 1906)
petr eth. Can be prepd by treating 2,4,6-trinitro-
Benzoyl Nitrite (called Nitrosylbenzoate in Ref 2),
benzoic acid with PC15 or with POC13. Sudborou#
C6H5.C0.0.NO; mw 151.12, N 9.27%; yel, un-
(Ref 3) warns of danger of expln during prepn.
stabIe and hydroscopic oil; expl on sudden heat-
Expl props of the compd were not investigated
ing; can be prepd by treating silverbenzoate in
Refs: l)Beil 9,417 2)V.Meyer,Ber 27,3145(1894)
the cold with nitrosylchloride
3)J .J .Sudborough,JCS 67,6oo( 1895) 4)P.J.
Re/.s: l)Beil 9,181 2)L.Francesconi & U. Cialdeq
Montagne,Rec 21,381-2(1902) 5)E .W.Crunden &
Gazz 34 1,444(1904)& JCS 86 1,707(1904)
R. F. Hudson,JCS 1956,507 &CA 50,9837( 1956)
(The rate of solvolysis of 2,4,6-trinitrobenzoy1-
Benzoylperchlorate or Benzoyliumperchlorate.
chloride)
This compd, prepd in situ from equimolecular
4.[(N.Benzoyl.N.ethyl).amino].naphtholen-e.1•di.
quantities of benzoylchIoride and Ag perchIorate,
azonium Hydroxide [called N-Athyl-N-benzoyl-
proved to be an effective benzoylating agent
naphthylamin.(l)-diazoniumhydroxyd. (4) in Ger], Re/.s: l)BeiI- not found 2)H.Burton & P.F.G.
C6H5. C0.N(C2H5)-C 10 H6.N(~N).0H; known Prail,JCS 1951,529& JCS 1953,827
in the form of salts, such as P ercldorute, C,9
H ,6 N30.C104, pale yel trysts explg on heating Benzoylperoxide. See Dibenzoylperoxide
to ca 154° or on impact; was prepd by treating the
corresponding sulfate with K perchlorate Benzoylperoxymonosulfonic Acid (called Benzoyl-
Refs: l)Beil 16,(374) 2)G.T.Morgan & E.G. sulfomonopers~ure in Ger), C~H5 .C0.0.0.S03H;
Couzens,JcS 97,1695(1910) known only in the form of salts, such as Potas-
sium saZt, KC7H~06S, hydroscopic ndls(from
Benzoylhydrazide, Dinitro, See under Benzoic ale), explg mildly on frictioq or on heating to 70
Acid -80°; can be prepd by treating benzoylchloride
(previously neutralized by KOH soln) with K2-
Benzoylhydroperoxide or Benzoylhydrogen Per S05 soln(or Care’s acid soln neutralized with
oxide. See Perbenzoic(Peroxybenzoic) Acid KOH) at 0°
Refs: I)Beil 9,181 2)R.WiIlst~tter & E. Hauen-
Benzoyliumperchlorate See Benzoylperchlorate stein,Ber 42, 1846(1909)

Benzoyl Nitrate and Derivatives (1.Benzoy1.1V.tetrazolyl.5).isotetrazene; 5.Benz.

Benzoyl Nitrate; C6 H.. .C0.0.N02; mw 167.12, amidotriazeno)-tetrazole 1.Benzoy1.4.tetrazolyl
N 8.38%; yel oil, expl on sudden heating; decornp .isotetrazene, C6 H5C0.NH.NH.N:N-$ -NH-N; mw
rapidly by w into benzoic and nitric acids. Can ~ —A
be prepd by the action of Ag nitrate upon benzoyl- 232.21, N 48.26%; wh ppt, mp 948° for the crude
chloride at -150 without presence of any moisture. product. This high-nitrogen compd was obtd by
It is a powerful nitrating agent which shows great Scott et aI(Ref 2) on adding a soln of 0.01 mol of

,
 B 91

tetrazolyldiazonium nitrate to a soln of 0.01 tnol 9.15%; oil, bp 106° at 20mm; dec explosively at
of benzohydrazide in aq SIC soln in the presence 180-200°. Can be prepd by several methods, such
of excess Na acetate soln. As most purifica- as action of Ag nitrate on benzyl haIide(Refs 1
tion techniques resulted in decompn of this & 3), oxidation of toluene with nitric acid+N
isotetrazene, it was not purified oxides(Ref 2), etc
Re/s: l)Beil- not found 2)F.L.Scott,D.A. O’Sul- Re/s: l)Beil 6,439 2)A.I.Titov,ZhObshchKhim
livan & J. Reilly,JACS 75,5309& 53 12( 1953): 18,534ff( 1948) & CA 43,4216(1949) 3)J.W.Baker
& T. G. Heggs,Chem&Ind ]954,464 & CA 49,
CA 49, 169(1955)
6872( 1955)
Bertzozone. See Acetylbenzoylperoxide in Vcd 1, Mononitmsobenzyl Alcohol, C)N. C~H4.CH2.0~
p A54-R mw 137. 13,N 10.2 1%. The 2-NitrosoaIcohol is de-
scribed in Beil 6,447 &(222)
Benzyl Abietate. See Vol l,p A3-R Mononitrobenzyl Alcohol, 02 N.~H4.CHz.0H; mw
153.13, N 9.15%. The isomers 2-,3- and 4-iVitro
Benzylacetyl Peroxide. See Acetylbenzylperoxide, are described in Beil 6,447,449,450,(222) & [424]
Vol l,p A55-L Nitrobenzyl Nitrite, 02 N.C6H4 .CHZ.O.NO; mw
182.13, N 15.38%. $he 4-Nitro-nitrite was obtd
Benzyl Alcohol and Derivatives by Komblum et al as a yel oil, bp 98° at 2mm Hg,
Benzyl Alcohol; Pbenylmetbanol or Hydmxytol- n ~ 1.5498 at 20°, on treating p-nitrobenzyl alco-
u ene (called l’-Oxy-l-methyl-benzol and ro-Oxy hol with Na hydride in dry benz
-toluol in Ger), C6H~ .CHZOH; mw 108. 13; CO1 Re/s: l)Beil- not found 2)N.Kornblum et al,
Iiq, d 1.043 or 20/4°, n~ 1.5403 at 20°, fr p-15.3~ JACS 77,6277( 1955)&CA 50,8492(1956)
Nitrobenzyl Nitrate, 0ZN.CGH4.CHZ.0.N02; mw
bp 204.7°, fl p 213°F(100.60) (closed cup} sol
in w; mist with aIc, eth or chlf. Can be prepd by 198.13, N 14. 14%. The following isomers are
hydrolysis of benzylchloride with Na or K carbon- known: 2-Nitro-, soIid, mp 28°, prepd by refluxing
ate in solrt or by other methods. There are two 2-nitrobenzyl chloride with finely powdered Ag
commercial products: technical grade and “I?FC”. nitrate for 7 days(Ref 4) 3-Nitro-, pale-yel trysts
mp 42.5-43°, prepd as above from 3-nitrobenzyl
(free from chlorine) grade(Ref 3). Toxicity and fire
hazard are discussed in Ref 5. It is used extens- chloride(Ref 4) and 4-Nitro-, yel trysts, mp 71°
(Ref 1), 520(Ref 2) and 68.2° (Ref 3); can be prepd
ively in many branches of the them industries,
by nitration of p-nitrobenzyl alcohol(Refs 1 & 3);
such as, for the manuf of esters (acetic, ben~oic,
by gradual introduction of benzyl nitrate into an
sebacic, etc), as a solvent for cellulose esters &
excess of 95% nitric acid cooled to -10° (Ref 2)
ethers, etc. During WW I, it was used in a “dope’
or by refluxing 4-nitrobenzyI chloride with finely
for airplane fabrics powdered Ag nitrate for 7 days (Ref 4). It is a
Re/s: l)Beil 6,428,(217) & [403] 2)0rgSynrh 18, mild expl and Blatt(Ref 3) lists its sensitivity to
( 1938),80 3)Kirk & Othmer 2(1948 ),484-6 4)Cond initiation as follows: 90.4 g undergoes only par-
ChemDict(1950),93 5)Sax( 1957),352 tial detonation with 0.4 to 0.7 g of 9010 fulmin-
Benzyl Nitrite, CeHs .CH2.0.NO; mw 137.13, N ate-chlorate mixture”
10.21%; unstable oil, bp 80-83° at 35mm. Can be Refs: l)Beil 6,452 2)Beil 6,[426] 3)Blatt,0SRD
prepd by several methods, such as action of Na 2014(1944) 3)J.W.Baker & T. G.Heggs,JCS 1955,
nitrite on benzyl alcohol in cold aq sulfuric acid 627 & CA 50,7081(1956)
(Ref 1), action of nitric acid+N oxides on C6Hs - Nitrobenzyl Dinitrate or m.Nitrophenyldinitro
.CH2 .HgC12 at low temp(Ref 2) or treating benzyl methane, 02N.C6H4 .CH(N02)z; mw 227.13, N
bromide with ~a nitrite in dimethylformamidine 18.50%; nearly CO1 prisms, mp 128-30°; can be
soln contg urea. Infrared spectra detd by T arte prepd by treating phenyldinitromethane with fum-
(Ref la) ing nitric acid(d 1.5), cooled to -15°(Refs 2 & 3).
Re/s: l)Beil 6,439 la)P.Tarte,BulI”Belg 60,240 This isomer of TNT is an expl more powerful
( 1951)& CA 46,826(1952) 2)A.I.Titov & D.E. than TNT. Its Ag, Amm, Ba, K & Pb salts are
Rusanov,DoklAkadN 82,65 ff(1952) & CA 47,2688 powerful expls(Ref 2)
(1953) 3)N.Komblum et al,Chem&Ind 1955,443 & Refs: l) Bejl- not found 2)M.MiIone & A. Massa,
CA 50,4805(1956) Gazz 70,196(1940) & CA 34,4571(1940) 3)L.
Benzyl Nitrate, C6H5.CH2.0N02; mw 153.13, N Fieser & W.von E.Doering,JACS68,2253 (1946) &
 B 92

CA 41,733(1947) (02 N~C6H2.CH2.0.N02; mw 288.13, N 19.45%,

Dinitrobenzyl Alcohol, (02 N)2C6H3.CH20H; mw OB to C02 -38.9., OB to CO O. O%; CO1 prisms,
198.13, N 14. 14%. The following isomers are de- mp 118.5-119.5°, d(cryst) ~. 5; inso] in W, s~ SOI
scribed in the literature: 2, 4-Dinitrober.zzyl in ether; sol in acet or methanol. Can be prepd
Alcohol, It yel ndls(from w), mp 114-5°; easily sol by nitration of 2,4,6-trinitrobenzyI alcohol(see
in alc or ACOH; insol in ligroin; can be prepd by above) with fuming nitric acid(d 1.5), but this
treating 2,4-dinitrobenzyl acetate with aq sulfuric method is Iess satisfactory than treating 2,4,6
acid( 1: l)(Refs 1 & 3). Its expl props were not -trinitroben zylbromide with Ag nitrate in ace to-
investigated and 2, 6- Dinitrobenzyl Alcohol, nitrile soln(Refs 2,5 & 6)
brownish plates(from ether), mp 94°; can be prepd TNBzIN is an expl about as powerful as tetryl
by heating 2,6-dinitrobenzyI bromide with w(Refs (ca 126-7% TNT by BaNistic Mortar Test) and
2 & 4). Its expl props were not investigated S1 less sensitive to impact than PETN. It pos-
Re/s: l)Beil 6,453 & [426] 2)Beil 6,(224 )&[426] sesses adequate stability and favorable oxygen
3)P .Cohn & P-Friedl~nder, Ber 35,1266( 1902) balance to CO: C7H4N409 -+ 7C0 + 2H20 + 2N2
4)S.Reich et al,Ber 45,3058(1912) 5)G.Williams Its expl and other props, given in Refs 2,3,4
& D. J. Clark,JCS 1956,1304 & CA 50,16697( Ester- & 5), are as follows: Ballistic Mortar Value
ification of 2,4-nitrobenzyl alcohol with aq sulf- (Power) 127%TNT; Explosion Temperature ig-
uric acid) nites ca 340°, but does not expl even at 360°
Dinitrobenzyl Nitrate(DNB zIN) (02 N)2C6H3 - (same as for TNT); Friction Sensitivity- S1 less
CH2.0NOZ; mw 243.13, N 17.28%, OB to C02 sensitive than RDX; Heat of Combustion, Qc 769.8
-62. 5%. The isomer 2, 4-Dinitro-, trysts, d 1.55 kcal/mole; Heat of Explosion, Qe 272.6
at 25°, mp 38.8°, expl ca 180°(in 5 reins). It was kcaI/mole; Heat of Formation, Qf 27.8
prepd prior to 1944 by the DuPont Co through the kcal/mol; Hygroscopicity- increase in wt at 100%
following steps: Benzyl chloride 2,4-dinitrobenz- RH 0.09% vs 0.03% for TNT; not hydroscopic at
yl chlorid~ 2 ,4-dinitrobenzyl alcohol+ 2,4-dinitr~ 90% RH; Impact Sensitivity, detd by BurMinesApp
benzyl nitrate No 5- S1 less sensitive than PETN; 7-5° lrzter-
DNBzIN is an expl about 70% as powerful as national Heat Test- loss of wt in 48 hrs O.l Z vs
NG(by the T rauzl Test) and fairly stable in 0.2% for TNT; Power- see Ballistic Mortar Value
storage at 60 & 75°. It can be detonated by a harm and Trauzl VaIue; Stability, Thermal at 100°- no
mer blow but not from the impact of an 8-oz wt expIn in 300+ mins(same as for TNT); Stability,
falling from a height of 25’’(Ref 2) ‘Thermal at 135°- methyl violet tutned salmon
Re/.s: l)Beil-not found 2)Blatt,0SRD 2014(1944) pink in 30 reins vs 300+ reins for TNT; Temper-
Note: No other Refs were found for DNBzIN ature of Explosion 3885°K; Trauzl Test Value
Trinitrobenzyl Alcohol, (02 N)~CGH2 .CH2.0H; 135% TNT
mw 243,13, N 17.28%. one isomer, 2,4, 6Xn’nitro- Uses- no information at our disposal
benzyl Alcohol, is described in the literature. It Remark: According to Ref 5, TNBzIN is a pre-
was first obtained by Reich et al(Ref 2) on heat- cursor of the Wlbite Compoun~See 2 ,2’-Azoxybis
ing 2,4,6-trinittobenzylbromide with water, as brn (4,6-dinitrobenzoic acid) under Dinitrobenzoic
ndls(from benz+ Iigroin), mp 100°; easily sol in Acid] an oxidative by-product in the manuf of TNT
ale, benz or etheG moderately sol in hot w; diffc by continuous method
sol in chlf or CS2; insol in ligroin. Ganguly(Ref Refs: l)Beil- not found 2)L. Fieser,0SRD 176
5) prepd the same compd(mp 100°) by refluxing (1941),27-38 3)G.B.Kistiakowsky,0SRD 702
2,4,6-trinitrobenzylbromide with w for 6 hrs. (1942) 4)R.McGill,OSRD 830(1942) 5)Blatt,0SRD
Fieser & Doering(Ref 4) prepd it as yel prisms, 2014(1944) 6) L. F. Fieser & W.von E. Doering,
mp 118-20° by nitration of benzyl alc with fum- JACS 68,2252(1946& CA 41,733(1947)
ing nitric acid(d 1.5), previously chiIIecl to -15°.
Its expl props were not investigated Tetranitrobenzyl, C7H3N50, ,- not found in Beil
Refs: l)Beil 6,(224) & [426] 2)S.Reich et al,Ber or in CA thru 1956
45,3058(1912) 3)K.L.Ganguly,Ber 58,712(1925)
4)L.Fieser & W.von E. Doering,JACS 68,2253 Benzylamine and Derivatives
(1946) &CA 41,733(1947) Benzylczmine(called l’-Amino- l-methyl-benzol and
u-Amino-toluol in Ger), CGH5 .CH2 .NH ; mw
2,4,6 TRINITROBENZYL NITRATE(TNBzIN), 107. I.5, N 13.07z, liq, dO-o$12 at 20/4%, bp l~4050;
 B 93

mist with w, alc or eth. Other props and prepn in mp 37-8°, bp 306° at 759mm. Other props &
Beil 12,1013(445) & [540] (Compare with AmJno- prepn are given in Beil 12,1023(449) & [548]
toluene in Vol 1, A264-L) Note: Nitration of benzylaniline and of its de-
Benzylanzine Nitrate, C7H9N + HNO ; mw 17$17, rivatives is discussed by P.van den Berg,Rec
N 16.46%; pltlts, mp 136-138.5°, Q! 942.7kchl/- 55,241-53 & 1053-67( 1936)
mol, Qf 57.2kcal/mol; can be prepd by neutraliz- Mononitroben~laniline, C, ~H ,2 N20Z; mw 228.24,
ing benzyl amine with 70% nitric acid and removi- N 12.27$%. Several isomers are described in Beil
ng w by distn in vacuo I2,1024, 1076,1083,1085,(466) & [549,577,579,
Re/.v: l)Beil I2,1018 2)T.L.Cotrrell & J. E.GiIl, 581] and by P. van den Berg,Rec 55,848
JCS 1951, 1798-9&CA 45,10028( 1951) Dinitrobenzylaniline, Cl ~ H,, N304; mw 273,24,
Benzylamine Perchlorate, C7H9N + HC104, soIid, N 15.38%. Several isomers are described in Beil
mp 120°, expl at 305° 12,1024,1077,1085,1086, 1088,1089, (450, 467)
I?e/s: l)Beil 12,(.466-7) 2)R.L.Datta & N.R. & [549, 762] and by P. van den Berg,Rec 55,842,
Chatterjee,JCS 115,1009(1919) 843,844,849, 850 & 1061
Benzylamine Picrate, C7HQN+ C6H3N307; mw Trinitrobenzylaniline, Cl~H10N406; mw 318.24,
336.26, N 16.66%; It yel trysts, mp 194-9°, d N 17.6 I%. The foHowing isomers are described
1.536; can be prepd by adding benzylamine to an in the literature:
equi amt of PA in boiling w. Its expl props were N-B enzyI-2, 4,6- trinitro-aniline, 2,4,6- Trinitro-N
not investigated -benzylaniline or N-PicryIbenzylamine, C6H5 -
Re/s: l)Beil 12,1018 2)C.Moureau & I. Lazennec, cH2.NH.C6H2(N02)~; yel ndls, mp 144.8 °(Ref
CR 143,553(1906) 3)G.Jerusalem,JCS 95,1283 2); crpts, mp 143°(Ref 4); crysts(from alc+di-
( 1909) oxane), mp 142 °(Ref 5). Can be prepd by warm-
Mononitrobenzylamine, 02N.C6H4 .CH2.NH2; mw ing methylpic~lnitramine with benzyIamine in
152.15, N 18.41%. All three isomers, 2-, 3-, ‘and aIc(Ref 2) or by adding, dropwise, benzylamine
4-Nitro, are described in Beil 12,1076, 1083, LO84, to a boiling alc soln of picrylchloride( Refs 3 &
(466) & [576,578,580] 4). This compd was also prepd by Leandri &
Beruzylnitrarnine, CeH~.CHz.NH.N02; mw 152.15, Tundo(Ref 5). Its expl props were not detd
N 18.41%, ndls, mp 38-9°, is described in Beil Refs: l)Beil 12, [549] 2)T.C.James et al,JCS
16,(396) 117, 1275( 1920) 3)M.M.CuIlinane et al,JCS 1932
Nitrobenzylnitramine, 02N.CeH4.CH2.N.N02; 2363 4)P. van den Berg,Rec 55,845(1936) 5X.
mw 197.15, N 2 1.32%. The isomer 4-iVitro, trysts Leandri & A. Tundo, AnnChim(Rome) 44,479-88
(from benz or from aq ale), mp 116°; was prepd ( 1954)&CA 49,15783(1955)
from benzylurethane as described in Refs 1 & 2. N-(2,4, 6- Tnnitrobenzyl)- aniline or PbenyI-(2,4, 6
Its expl props were not detd -trinitrobenzyl)- amine, (02 N)3C6H2 .CH2.NH.C~-
Refs: l)Beil 16,673 2)A.Hantzsch,Ber 31,181 H5; brn ndls, mp 15 1°; can be prepd by heating
(1898) 2,4,6-trinitrobenzenebromide with aniline in benz.
Dinitrobenzylamine, (02N)zC~H3 .CHZ.NH2; mw Its expl props were not detd
197.15, N 21.32%. Its 2, 6-Dirzitro*isomer, brn fidls, Refs: l)Beil 12,(468) 2)S.Reich et al,Ber 45,
mp 88°, is described in Ref 1, while the 2,4-Di- 3058(1912)
nitro-isomer, brn ppt, mp 179°, it described in 4’-Nitrobenzyl-2,4-dinitroaniline, 02 N.CGH4 .CHZ
Ref 2. Their expl props were not detd NH.C~H3 (N02)2; brn ndls, mp 186°; easily sol
R e/s l)Beil 12,467 2)K.A.de Vries,Rec 61,236 in acet & warm AcOH; SI sol in ale, benz or chlfi
& 238(1942)& CA 38,2313(1944) v SI sol in ether or petr eth. Its method of prepn,
Dinitrobe~~lnitrmitie, (02 N)2C6H~ .CH2.NH(N02) starting from 4-nitroben zylchloride and ammonia,
and Trinitrobenzylnitrarnine ,(02N)3 C6H2 .CH2 .NH- is described in Ref 2
(N02)- not found in Beil or in CA thru 1956 Re/.s: l) Beil- not found 2)P. van den Berg,Rec
55,845-6(1936)
l. Benzyl.5.amin.vic.tetrazole. See ~Amincwl Tetranitrobenzylaniline, Cl ~H9N50e; mw 363.24,
-Benzyl-vic-tetrazol~ Vol l,p A191-L N 19.28%. The following isomers are described
in the literature:
Benzylaniline and Derivatives N-(2,4, 6- Trinitrobenzyl)-3-nitro arziline or (3-Nitro-
Benzylaniline or Pbenylbenzylamine, C~I-$ .CH: @enyl)-(2,4, 6-trinitrobenzyl)-amine, (02 N)3C6H2-
NH. C6Hs; mw 183.24, N 7.64%; monacl prisms, CH2.NH.Ce Ha .N02; red ndls, mp 153°; was prepd
 I

B 94

by heating 2,4,6-trinitrobenzy lbromide with 3-ni- mer is known:

troaniline in benz. Its expl props were not detd 2’,4’-Dinitrobenzy l-2,4, 6-trr”nitro-nitraniline; 2’,
Refs: l)Beil 12,(46s) 2)S.Reich et al, Ber 45, 4’-Dinitro-benzy l-2, 4, 6-trinitropbeny l-nitramine
3059(1912) or Picryl-(2,4-dinitrob enzyl)-nitramine, (02 N)2-
4’-Nitrobenzyl-2,4,6-trinitroaniline, 02 N. C6H4- C6H3 .CH2.N(N02 ). C6H.-(N02)3; nearly COI
.CH2 .NH.C6H2(N02 )3, red-brn soIid, mp 191°; crysts(from ale+ acet), mp 150- l“(with evoln of
easily sol in acet; less sol in chlf, benz or warm gas); easily sol in acet; moderately sol in warm
AcOH; S1 sol in ale; v diffc sol in eth or petr eth. ACOH; diffc sol in ale, benz or chlf; insol in
Was prepd by mixing alc solns of 4-nitrobenzyl- eth or petr eth. Can be prepd by nitration of 2‘
amine and picrylchloride and boiling the mixt -nitrobenzyl-2,4 ,6-trinitronitraniline wi th abs
for 15 reins on a water bath. Its expl props nitric acid or by nitration of 4 ‘-nitrobenzylaniline
were not detd (or of benzyl-4-nitroaniIine) with mixed nitric
Re/.s: I)Beil- not found 2)P.van den Berg,Rec -sulfuric acid. Its expl props were not detd
55,846(1936) Re/s: l) Beil- not found 2)P.van den Berg,Rec
Pentanitrobenzylaniline, Cl ~H8N601 o; mw 408.24, 55,848-9(1936)
N 20.59%, OB to C02 -78.4%. The following iso- 2’,4 *,6’-Trinitroben~ l-2,4, 6-trinitro-nitraniline,
mers are known: (02N)3C6H2.CH2. N(N02).C6H2(N02)3; mw
2’. Nitrobenzyl-2,4, 6-trinitro-nitraniline or 2’-Ni- 498.24, N 22.49%-not found in Beil or in CA
trobenzyl-2, 4, 6-trinitropbenyl-nitramine, 02 N- thru 1956
C6H4 .CH2.N(N02 ). C6H2(N02)3; CO1 crysts(from
ale+ acet), mp 149°(with evoln of gas); easily SOI Benzylazide and Derivatives
in acet or warm AcOH; less sol in benz; S1 sol Benzylazide(called l’-Azido-I-methyl-benzol,
in alc or chlf; nearly insol in eth, petr eth or W. ti-Azido-toluol and cwTriazo-toluol in Ger),
Was prepd by nitrating 2 ‘-nitrobenzyl-4 -nitroani- C~H5.CH2.N3; mw 133.15, N 31.56%; oil, d
line or 2 ‘-nitrobenzyl-2-nitroaniline with nitric 1.0655 at 24.5°, nD 1.53414 at 24.9°, bp 82.5°
acid(d 1.46). Its expl props were not detd(Ref 2, at 16.5mm; expl on strong heating with evoln of
pp 850& 853) flame; also expl on contact with coned sulfuric
3’-Nitrobenzyl-2,4, 6-trinitro-nitraniline, almost acid. Insol in w, miscible with alc or eth; vol
CO1 crysts(from ale+ acet), mp 14~(with evoln of with steam or with ether. Can be prepd by treat-
gas), easily sol in acet or boiling AcOH; mod- ing benzyl chloride with Na azide in alc or by
erately sol in warm benz; less sol in ale, chlf, other methods
eth & petr eth. Was prepd by nitrating 3’-nitro- Re/s: l)Beil 5,350,(174) & [2741 2)T.Curtius,
benzyl-4-nitroaniline with abs nitric acid as de- Ber 33,2562(1900) 3)J.C.Phillip,JCS 93,919
scribed in Ref 2,p 1062. Its expl, props were not (1908) 4)T.Curtius & G. Ehrhart,Ber 55,1565
detd (1922)
Re/s: l)Beil- not found 2)P.van den Berg,Rec Mononitrobenzylazide, 02N.C6H4 .CH2 .N3; mw
55,850,853 & 1062(1936) 178.15, N 31.45%, OB to C02 -134%. PrePn of
4’-Nitrobenzyl-2, 4, 6-trinitro-nitranilinz; 4’-Nitro- O- and p-nitrobenzyl azides from Na(or Ag) azide
benzyl-2,4, 6-trinitrophenyl-nitramine or PicrY1-(4 and the appropriate chlorides or iodides in alc
-nitrobenzyl)-nitramine; nearly COI trysts, mp 141 or ether for 8-10 hrs at the bp, was described by
-2° (with evoln of gas); was first prepd by Blank- Yushchenko(Ref 2). He gave the bp of O- as 121
sma(Ref 2) by heating N-(4-nitrobenzyl)-4-nitre -2° at 2mm and of p- as 144-8° at 2mm. The Du-
aniline with nitric acid(d 1.52) and then later by Pont Co prepd, sometime before 1944, an impure
VarI den Berg(Ref 3), who showed that this comPd p-nitrobenzylazide by treating benzylchloride
can also be obtd by nitration of 4’-nitrobenzyl-2 with Na azide. The product had mp ca 5° and
-nitroaniline, benzyl-2,4-dinitroaniline, benzyl-2, could not be detonated by a 2-g steel ball fal-
4,6-trinitromiline, 4’-nitrobenzyl-2,4-dinitroani- ling 25” (Ref 3)
line or 4’-nitrobenzyl-2,4,6 -trinitroaniline. Re/s: l)Beil- not found 2)Yu.Yushchenko, Mere-
Its expl props were not detd InstChemUkrainAcadSci 2, 195(1935) & CA 31,
F!e/s: l)Beil 12,1089 2) J. J. Blank sma,Rec 21, 3467( 1937) 3)B1att,0SRD 2014(1944), under
429(1902) 3)P.van den Berg,Rec 55,843-7(1936) Azides
Hexonitrabenzyl aniline, Cl ~H7N701 ~; mw 453.24, Dinitrobenzylazide, (02 N)2C6H3.CH2.N~; mw
N 21.63%, OB to C02 -6 1.8%. The following iso- 223.15, N 31.39%. Its 2,4- Dinitro- isomer is a
 B 95

solid, melting at 46-7°. It was prepd by Yush- Z?e/s l)Beil 9,[ 101] 2)K.A.Krassukii & A.H.
c henko by treating 2,4-dinitrobenzy lchloride PIissov,UkrainskiiKhemZhurnal 1,640( 1925);
with Na(or Ag) azide in alc(or ether) for 8-10 hrs ChemZtr 1926 II, 193 & CA 21,2457(1927)
at the bp. Its expl props are not described in CA Mononitrobenzyl Dinitrobenzoate, (02N)2C6H:
Re/s: l)BeiI- not found 2)Yu.Yushchenko, Mem COz.CH2.C~H4.N02; mw 374.24, N 12.10%. only
InstChemUktainAcadSci 2, 195(1935) & CA 31, the 4-Nitrobenzyl-2,4-dinitroberzzoate is describ-
3467(1937) ed in the literature: cryst$(from boiling ale), mp
Trinitrobenzylcrzide, (02N)3C6H2 .CH2 .N~- not 142°; very sl sol in boiIing aIc; was prepd by
found in BeiI or in CA thru 1956 heating the Na salt of 2,4-dinitrobenzoic acid
with 4-nitrobenzyl bromide in boiIing ale. Its expl
Benzylazidodithiocarbonate. See Vol l,p A633-L props were not detd
Re/s: l)Beil 9,(166) 2)E.M.Reid,JACS 39,133
Benzylbenzoate and Derivatives (1917)
Benzylbenzoate( Benzyl Ester of Benzoic Acid) Tetranitro- Cl ~ H~N401 ~, Pentanitro- Cl ~H7N5 -
(called Benzoes~urebenzylester or Benzylbenz- 01 ~ and Hexanitro- Ct4H6N60, ~ Derivatives of
oat in Ger), C6H5C02.CH2.C6H~; mw 212.24, C Benzyl Benzoate were not found in Beil or in CA
15.08~, OB to COZ -241%; liq at RT, ndls or lfts thru 1956
on prolonged cooIing, fr p 19.4-21°, bp 324° at
i’60mm, dec on kating for 2hrs at 340-50°, d Benzyl Chloride and Derivatives
1.112 at 25°; SOI in acet, ale, AcOH, chlf, CS2, Benzyl Cblotide; r+ Cblorotoluene or l’-CHoro
eth, benz, MeOH, petr eth or xylol; insol in w “or - I-rnetbyl-benzene, C6H5 .CH%C1; COI Iiq with
glycerin; toxicity discussed by Sax(Ref 3); can pungent odor, d 1.00 at 20/20 , fr p -39°, bp
be prepd by heating benzoic acid with benzy$ 179.4°; mist with ale, eth or chlf; insol in w.
alcohol at the bp or in the presence of tin at 200°. Other props and various methods of prepn are dis-
Other props and methods of prepn are given in Ref cussed in Ref 1; its toxicity, fire & expln hazards
1 are given in Ref 2
Davis(Ref 2) reported its possible use as a gel- Refs: l)Beil 5,292,(151) & [227] 2)sax(1957),
atinize for NC 353
Re/s: l)Beil 9,121,(68) & [1OO] 2)Davis(1943), Note: F; Oebme, CbemTecb 4,404(195$& C} 47,
p 320 3)Sax(1957),p 353 1277(1953) (During distn of the tech product, HCI
Benzyl Mononitrobenzoate, 0,N.~H,.C02.CH2- was evoIved and air was bubbled through the soln
Cc~ ; mw 257.24, N 5.45%. One isomer, to remove HCL Suddenly, an expln occurred and
4-~itro- is described in Beil 9, 392 the reaction mass became an orn-grn, fluorescent,
Mononitrobenzyl Monorzitroberzzoate, 02N. CG~- very viscous mass)
CO,. CHZ.C,H4.N0,; rnw 302.24, N 9.27%. The
Mononitrobenzyl Chloride, C7H6CIN02. TIE iso-
following isomers are described in the literature:
2- Nitrobenzyl-2-nitrobenzo@te, trysts, mp 1046° mers: 2-,3-, and 4-Nitrobenzylchl orides~ are de-
(Ref,p 373) scribed in Beil 5,327-31,(162-3) & [252-4]
3-Nitrobenzyl-3 -nitrobenzoate, yel trysts, mp Trinitrobenzyl Chloride, C7H4ClNsOG; mw 261.54
143-4°(Ref~p 379) 4-Nitroben&-4-~ itrobenzo- N 16.06%, OB to COZ -6 L 1%. The isomer, 2,4,6
ate, yel trysts, mp 168-172° [Ref,p 392 & (159)] -Trinitrobenzyl Cbtoride or u- Cbloro-2, 4, 6-t~nit~
4-Nitrobenzyl-2-nitrobenzoate, trysts, mp 1 Il.@ toluene, ( O *N)3CGH2.CH2 .Cl; crysts(from ale),
[Ref,p (159)] ~d 4-NitrobenwZ-3-nitrobenzoate, mp 85°; v sol in benz or eth; SOI in hot ale; insol
trysts, mp 141.5° [Ref,p(154)] in w or cold alc, was obtained in small quantity
Refl Beil 9,373,379,392 & (152,154,159) by Ganguly on prolonged heating in a sealed tube
Dinitrobenzyl Benzoate, C6Hs.COz .CH2.CeH3- at 150.60°, of 2,4,6-TNT with PC15 ~d some
(N02)2; mw 302.24,N 9.27%. Only the 2,4-Di- iodine. Its expl props were not detd
nitrobenzyl- b enzoat e is described
in the litera- Refs: l)Beil 5, [272] 2)K.L.Ganguly,Ber 58,711
ture: yel ndls(from glac AcOH), mp 141°; insol (1925)
in ale, eth, benz or w; was prepd by the action Tetranitrobemyl Chloride, C7H~ClN~Os- not
of K benzoate on 2,4-dinitrobenzyl chloride in found in BeiI or in CA thtu 1956
boiling methanol or ethanol
The gelatinizing props of benzyI benzoate sug- Benzyl Cyanide and Derivatives
gest that nitro or dinitro derivs may also be used Benzyl Cyanide or Pbenyl Acetoniti”le (celled
as gelatinizing agents for NC
 B 96

Benzylcyanid, Phenylacetonitril or Phenylessig- Benzyldiphenylamine or Diphenylbenzylamine,

s~ure-nitril in Ger), C~H~.CH2.CN; mw 117.14, C6H5CH2.N(C6H5)2; mw 259.33, N 5.40%, OB
N 11.96%; oily liq with aromatic odor, fr p to CO - 138.9%; CO1 ndls, mp 86-87°; sol in acet,
-23.8°, bp233.50, d 1.021 at 15°; toxicity is eth, chlf, benz & hot ale; diffc sol in ACOH &
discussed in Ssx(Ref 2); other props &prepn are cold ale; v S1 sol in w. Other props & prepn are
given in Beil(Ref 1) described in Ref 1. Because this compd may be
Re/s: l)Bei19,441,(176 )& [302] 2)Sax(1957), suitable as an ingredient of propellants, Taver
355 & 521 nier & Lamorous detd its calorimetric props.
Morzonitrobenzyl Cyanide, 02N.C6H4.CH2.CN; They gave Q: 2413.8kcal/mol, ~ 2415.98kcal/
mw 162.14, N 17.28%. Three isomers 2-,3- and mol, Q; -44.4 kcal/mol and Q? -39. lkcalz’mol
4-Nitrobenzyl Cyanides are described in Beil Re/s: l)Beil 12,1033 & [551] 2)P.Tavemier &
9,455,456,(182, 183) & [311,312,313] M. Lamouroux,MP 38,77 & 84( 1956)
Dinitrobenzyl Cyanide, (02N)2.C6H~.CH2 .CN;
mw 207.14, N 20.29%. Two isomers are described Benzylester of Benzoic Acids See Benzyl B enzo-
in the literature: 2,4-D initrobenzyl Cyanide, yel ate
ndls(from CC14 ), mp 89° and 2, 6- Dinitrobsnzyl
Cyanide, yel-brn crysts(from nitrobenz+alc), mp Benzylester of Peracetic Acide See Acetylbenzyl-
202°. Other props and their prepn are given in peroxide, Vol l,p A55-L
Beil 9,(185) & [3 15]. These compds are evident-
ly expl but this was not detd Benzylethylene Ozonide (called l-Phenyl -a
Trirzitrobenzyl Cyanide, C8H4N406- not found -propylen-ozonid, Phenylallyl-azonid or Allyl-
in Beil or in CA thru 1956 benzoI in Ger). The monomeric ozonide, C9H1 oo~;
liq, bp 67-71° at 0.4-O.8mm, d 1.1362 at 21/21°,
Benzyldimethylhexadecylammonium Chloride, was obtained together with the dimeric form by
C6H5.CH2(CH3 )2.N(Ct ~H3 ~ )C1. A quatemary treating allylbenzene, C6HS .CH2.CH:CH2, in
ammonium halide recommended by McDonald(R ef CC14 soln with purified ozone. It is a weak expl,
2) as satisfactory for the decontamination of difficultly sol in w. The dimeric ozonide, C9-
waters contg dissolved expl wastes. This, or Ht 003)2, was septd fr’om the monomeric ozonide
other halide salts, can be added to a tank along by dissolving the reaction mixture in acet eth
with the waste water; the expl material settles and pptg with petr eth. It is a syrupy liq, d 1.766
as an insol addn compd at 21/21°, n~ 1.5422, which decompd ca 100°
Refs: l)Beil- not found 2)L.McDonald,USP and exploded violently at 104-6°. More diffc sol
2647084(1953) & CA 47, 10853( 1953) in w than the monomer
Re/s: l)Beil 5,(233) 2)C.Harries,Ann 390,261-3
4.Benzyl.3,5.dioxo.4.pyrazolidineacetyl Azide ( 1912)
or a-Phenylpropane-,y.tricarboxylic Hydra.
zoazide (called m PhenyI-propan-~, /3 ,ytri- Benzylic Acid Same as Phenylacetic Acid
carbons~ure hydraziazid by Curtius),
,CO.NH l.Benzylideneamino.5.amino.a(or lH)tetrazole;
C&H5.CH2.C1 I ; mw 273.25, N 25.63%; 5.Amino.benzylideneamino.l,2,3,4.tetrazole or
I CO.NH l.Benzalamino.5.aminotetrazole,
CH2.C0.N9 H2N.$ (N: CH.C6H5)-~; mw 188.19, N 44.66%;
lt yel pdr, mp dec at 202-3° with evoln of gas; N d
defgr when heated on a Pt foil in flame; could fine ndls, mp 210° (with rapid evoln of gask
not be obtained in c~st state because it is in sol moderately sol in hot ale; diffc sol in eth; insol
in neutral solvents such as eth, benz or chlf and in w; was prepd by shaking for 8 hrs a mixt of
is decompd by solvents such as ale. Can be prepd thiosemicarbazide, Na azide and Pb oxide in
by adding dropwise aq NsN02 soIn to the corre- boiling ale. It might be suitable as an in-
sponding hydrazohydrazide dissolved in cold dil gredient of propellants
HCI Re/s: l)Beil- not found 2)R.Stol16 &E .Gaertner,
Refs: l)Beil- not found 2)T.Curtius & W. Sand- JPraktChem 132,210& 214(1931)& CA 26,1607
haas,JPraktChem 125,93 & 100-1(1930)& CA (1932)
24,3231(1930)
 B 97

l.Benzylideneamino.5.anilino.a(or 1H)-tetrazole, 4-(2,4,6.Trinitrobenzylideneamino).phenal,

l.Anilino.1.benzylideneamino.l,2,3,4.tetrazole or (02N)3 .C6H2.CH:N.C6H4 .0H(?); mw 332.23, N
1.Benzalamino.5.anilino.tetrazole(caIIed BenzaI- 16.87%; yeI crysts(from sic) sensitive to light,
amino- l-anilino-5-tetrazol by %oll~), CGH5.NH* mp 179°; was prepd by condensation of 4-amino-
C-N(N:CH.CeH5)-N; mw 264.28, N 31.80%; ndls phenol and 2,4,6-trinitrobenzaldehyde in glac
A N ACOH, on a w bath. Its expl props were not detd
Or Ifts(from ale), mp 2 16°; S1 SO1 in eth & ale; in- Refs: l)Beil 13, [236] 2)A.Lowy & E. H. Balz,
SO1 in w; was prepd by shaking for 12 hrs a mixt JACS 43,345(1921)
of 4-thiosemicatbazide, Na azide and Pb oxide in Tetranitro-C,~~7N509 and Pentanitro.C1 ~H6N6-
boiling ale, while bubbling in C02. Its expl props 01, B enzylideneaminopbenols were not found in
were not investigated Beil or in CA thru 1956
Re/s: l)BeiI- not found 2)R.Stol16 & E. Gaertner,
]PraktChem 132,210& 214(1931)& CA 26? l@8 l.Benzylideneamino.5.phenly-a(or 1H).tetrazole.
(1932) See l-Benzal-amino-5-phenyl -a(or lH)-tetrazole

Benzylideneaminophenol and Derivatives 5.Benzylideneamino.2.phenyl-(or2H)-tetrazole.

Benzylideneaminop benol or B enzalaminopbenol, See 5-Benzalamino-2-pheny l-~(or 2H)-tetrazole
(called Benzylideneamin&phenol or Benzalamino
-phenol in Ger),C6Hs.CH:N. C6Ha “OH; mw 197*23> Benzylideneaniline and Derivatives
N 7. 10%. This compd exists in two isorneric N-Benzylidenean (caIled
ilin e or Benzalaniline
forms: 2-Benzalaminopb-ol, Ifts(from de), mp Benzaldehyde-anil in Beil), C6H5 .CH:N.C6H5;
89° (Ref 1) and ~B enzataminopbenol, lfts(f~om mw 181.23, N 7.73%; yel ctysts; rep-melts at first
dil ale), mp 183°; its Hydrucblotide salt, C, ~H,, - at 48-9° and then, after solidification, remelts at
NO+HCI, yel ndls, dec ca 132° (Ref 2). Othet 54560 (the difference in rep’s is probably due to
props and methods of prepn are given in Refs several modifications of the compd); bp ca 300°,
Re/s: l)Beil 13,368 & (312) 2)Beil 13,453,(155) d 1.0739 at 50/13°; volatilized by steam. Other
& [236] props & prepn are given in Refs. Forms salts,
4-(4-Azidobenzylideneamino)-phenol, N3.C~F14.-
some of which ate probably expl, eg P ercblorate,
CH:N.CGH4.0H; mw 238.24, N 23.52%; goIden ctysts, mp 1790 (Ref Q [170]
-brn plates(from benz), mp 175° (dec); readily SO1 Re/s: l)Beil 12, 195,( 169). & [113] 2)OrgSynth
in hot acet or eth ace~ sol in boiling MeOH; SI COHVO1 1(1941),73
sol in boiling benz; was prepd by mixing aq p Mononitrobenzylidene@riline, C,~H10N202; mw
-aminophenol hydrochloride, Na acetate and p
226.23, N 12.38%. Its 2-,3- and 4-Nitro-isomers
-azidobenzaldehyde are described in Beil 12,702,717,(346,35 ~) &
Refs: l)Beil 13,(155) 2)M.O.Forster & H.M.Judd,
[3701
]CS 97 1,260(1910) Dinitmbenzylidenecrniline, C, ~H9N304; mw 271.23,
Mononitrobenzylideneaminopbenol, 02N.C6H4 .CH:-
N 15.49%. Eight isomers are described in Beil !2,
N. C6H4.0H; mw 242.23, N 11.57%. The nine pos-
199,702,(172, 346) & [370, 372,378 & 388]
sible isomers of 2,3 or 4-Monorritrobenzylidene- Trinitrobenzylideneaniline, Cl 3H8N406; mw
amino-phenol with the substituted mononitroderiv 316.23, N 17.72%. The following isomers are de-
in ortho(or 2)-, meta(or 3)-, and para(or 4)- posi- scribed in the literature:
tions with respect to the hydroxy group of phenol, N-(2,4, 6-Trinitrobenzylidene)-aniline, (OZN)3 C6H -
have all been prepd and described in the litera- CH:N.C6H5; reddish, small ndls(froni ale), mp 16 +
ture (Refs 1 & 2); 171 °(Ref 3); easily sol in benz;
Refi l)Beil 13,368,414,453,(133,135) & [236]
diffc sol in ale; insol in w; was prepd by heating
Dirzitrobenzylideneaminophenol, (02N)2C6H~ *CH:-
2,4,6-trinitrobenzaldehyde with aniline in alc
N.C6H4 .OM mw 287.23, N 14.63%. Only the #-(2, -
soln(Refs 1 & 2) or on interaction of the same
4-Din itmbenzylideneam ino)-pbewl is described
substances in cold AcOH(Ref 3)
in the literature: yel crysts(from ale), mp 158°;
Refs: l)BeiI 12,199 & [114] 2) F.Sachs et al,
was prepd by heating 4-aminophenol with 2,4kdi-
Ber 36,961(1903) & 39, 2761(1906) 3)S.Secareanq
nitrobenzaldehyde in alc gIac AcOH
BullFr 51,591(1932) & CA 26,5081(1932)
Re/s: l)Beil 13 [236] 2)G.M.Bennett & W.L.C.
N-(2,4-D initrobenzyIidene)-2-nitmaniline, (02N)2-
Pratt,JCS 1929, 1466
C6H~ .CH:N.C~H4.N02; yel, light-sensitive ndls
 B 98

(from ale, acet or toluene), mp 174.5°; easily sol Benzylidyneoxytetrazotic Acid, See Phenyloxy-
in chlf, benz or acet; diffc SOI in ale; insol in w; tetrazotic Acid
was prepd by heating 2,4-dinitrobenzaldehyde with
o-nitroaniline in AcOH soln(Refs 1 & 4) Benzylmalonic Acid and Derivatives
N-(2,4 -Dinitrobenzylidene)-3’-nitroaniline, yel BenzylrnaZonic Acid[called l-Phenyl-~than-di-
light-sensitive ndls(from ale, acet or toluene), mp carbons ~ure-( L 1) in Ger], C6H5 .CH .CH(COOH) “
138°; easiIy sol in chlf, benz, ale, acet or AcOH; mw 194.18, crysts(from eth), mp 1216, dec ca 180.%
insol in w; was prepd by heating 2,4-dinitrobenzal- Other props & prepn are given in Beil 9,868,(381)
dehyde with m-nitroaniline in 95% alc(Refs 2 & 4) & [619]
N-(2, 4-Dinitrobenzyliden e)-4*-nitroaniline, yel, p.Nitrobenzylmalonazidic Acid (called p-Nitro-
Iight-sens ndIs(from ale), mp 169. 5°; very sol in benzyl-malonazids~ure in Ger), 02N.C6H4 .CHZ
chlf, benz, ale, AcOH or acet; insol in w; was CH(C0.N3).COOH; mw 264.20, N 21.2 1%; fine
prepd by heating 2,4-benzaldehyde with p-nitro- ndIs(from eth), expl when heated on a metallic
aniline in alc soln(Refs 3 & 4) spatula in a flame; was prepd by tre sting p-nitro-
Refs: l)Beil 12, [370] 2)Beil 12, [379] 3)Beil benzylmaIonhydrazidic acid with aq Na nitrite
12, [388] 4)A.Lowy & T. B.Downey, JACS 43, as indicated in Ref 2. Its soln in eth is stable
347(1921) at RT
Tetranitrobenzylideneaniline, C13H7N50e; mw Re/s: l)Beil- not found 2)T.Curtius & W.M;hl-
361.23, N 19.39%, OB to Coz -95.2%. The follow- h~usser,JPraktChem 125,2$%(1930) & CA 24,3216
ing isomer is described in the literature: -17(1930)
N-(2, 4,6- Tn’nitrobenzylidene)-3 -nitroaniline, Benzylmalondiazide (called Benzylmalons~ure-di-
(02 N)3C6H2.CH:N.C6 H4.N02; yel trysts, mp azid in Ger), C6H~ .CH2.CH(C0.N3)2; mw 244.21,
161-2°; was prepd by interaction of 2,4,6-trinitro- N 34.42%; yel oil, expl on heating; sol in alc or
benzaldehyde with m-nitroaniline in cold AcOH. eth; insol in w; was prepd by treating benzyl-
Its expl props were not detd malondihydrazide in HC1 with coned aq soln of
Refs: l)Beil- not found 2)S.Secareanu,BullFr Na nitrite as indicated in Ref 2)
51,591(1932) & CA 26,5081(1932) 3)S.Secareanu Re/s: l)Beil 9,(382) 2) T. Curtius et al, JPrakt
& I. Lupus, JPraktChem 140,94( 1934) & CA 28, Chem 94,327(1916-17)& CA 14, 1670(1920)
5445(1934) Mononitrobenzylrnalonic Acid, Cl 0H9N06; mw
Pentanitro-C1 ~H6N60,0 and Hexanitro-C ,~H5N7- 239.18, N 5.86%. Its three isomers: 2-Nitro-,
0 , z, Derivatives were not found in Beil or in CA 3-Nitro- and 4-Nitro-, none of them expl, are de-
thru 1956 scribed in the literature
Refs: l)Beil 9,871 & [621-624] 2)J .W.Baker &
(N.Benzyliden-N’.azidomercapto}hydrazine. A. Eccles,JCS 1927,2127 & CA 22,65( 1928)
See 2-Benzylidene-thiocarbazoyl Azide 3)J.M.Gulland et sI,JCS 1929,1670 & CA 23,5186
(1929)
Benzylideneazine See Benzaldehydeazine Dinitrobenzylmalonic Acid, Cl 0HSN208 and Tri-
nitrobenzylmalonic Acid, C, 0H7N3 O,0 were not
2.Benzylidene.thioscarbazoyl Azide;Benzalthio. found in Beil or in CA thru 1936
carbazinic Acid Azide or (N- Benzylidene-N’
-azidomercapto)-hydrazine (called Benzalthio - Benzyl Nitrate, See under Benzyl Alcohol
carbazinsaureazid by Stol16), C6H5. CFI:N.NH.C-
(: S).N3; mw 205.30, N 34.12%; pale yel flakes, Benzyl Nitrite See under Benzyl Alcohol
.mp 173°, followed by an expl; sol in hot alc
or hot AcOH; insol in w; was prepd by shaking Benzyloxamic Acid and Derivatives
for 8 hrs a mixt of dithiocarbazinic acid Benzyloxamic Oxals;uremonobenzyl-
Acid(called
hydrazide, Na azide & Pb oxide in alc medium amid or Benzyloxamids~ure in Ger), C6H5.CH2.-
NH. CO. COOH; mw 79.17, N 7.82%; plates(from
Re/s: l) Beil- not found 2)R.Stol16 & E. Gaertner,
JPraktChem 132,225(1931)& CA 26, 1608(1932) w). mp 128-9°; other props & prepn are in Beil
12,1047-8
Benzyloxaminyl Azide, C6H5 .CH2 .NH.OC.CO.N~;
Benzylidyneoxyhydroxytetrazotic Acid See
Phenyloxyhydroxytetrazotic Acid mw 204.19, N 27.44%; lfts, expl at 80-90°; sol in
acet or chlf; diffc sol in eth or benz; was prepd
 B 99

by treating benzyloxaminyl hydrazide in HC1 with are given in the Ref. Its expl props were not detd
Na nitrite as described in Ref 2 Refs: Beil 6,[426]
Re/s: l)Beil- not found 2)T.Curtius & K. Raschig,
JPraktChem 125,484-5(1930) & CA 24,323 1(1930) Benzyl.2,4,6.trinitrophenyl Ether[caIIed Benzyl-
Morzonitro-, C9H8N205, Dirzitro-, C9H7N907 and pikrat; Pikrins~ureben.zyl- ~ther or (2.4 .6-Trinitro-
Trirzitro- C9H6N409 Derivatives were not found -phenyl)-benzyl-~ther in Ger],
in Beil or in CA thtu 1956 C6H5.CH2.0.C6HZ(N02 )3; mw 319.23, N 13.16%;
almost COI prism s(from benz), or pltlts(from ale),
Benzylperacetate See Acetylbenzylperoxide, Vol mp 145-147°; diffc sol in alc or eth; other props
l,p A5 5-L and method of prepn are given in Ref. Its expl
props were not detd
Benzyl Perchlorate, C6H5.CH2.C104. Button & Refi Beil 6,433
PrailI(Ref 2) mentioned that they prepd this compd 4.Nitrobenzyl.2,4,6.Trinitrophenyl Ether, 02N -
by the action of AgC104 on benzyl bromide in C6H4.CH2.0.C6H2 (N02)~; mw 364.23, N 15.38%;
benz with or w/o added nitromethane. No props almost COI crysts(from glac ACOH), mp 108°; v
are given. The same compd is mentioned in Ref SI sol in cold alc or eth; diffc sol in cold benz
3, where some reactions of benzylperchlorate are or glac AcOH; was prepd by heating, on a w bath,
discussed the Ag salt of PA and P-nitrobenzyliodide; other
Re/s: l)Beil- not found 2)H.Button & P.F.G. props are given in the Refs. Its expl props were
Praill,Chem&Ind 1951,939 & CA 46,6077(1952) not detd
3)Ibid,JCS 1953, 827 & CA 48,758(1954) Re/s: l)Beil 6,451 2)G.Kumpf,Ber I7,1075(1884)
& JCS 46 11,1005(1884)
Benzylphenyl Ether and Derivatives Pentanitro Derivatives of Benzylphenyl Ether,
BenzyIpbenyl Ether or Pbenylbenzyl Etber(CaHed C, ~H7N501 ,, mw 409.23, N 17.12%. Two compds,
PhenylbenzyI~ther in Ger),C6H~ .CH2.0.C6H5; it presumably: 2,4-Dinitrobenzy l-2,4, 6-trinitro-
is described in Beil 6,432,(220) & [411] phenyl Ether, (02N)2C6H3.CH2.0. C6H2(N02)3(? )
Mononitrobenzylphenyl Ether, 02N.C6H4 .CH2.0 - and 2,4,6- Trinitrobenzyl-2,4 -dinitropbenyl Ether,
C6H5; mw 231.24; N 6.06%. Two isomers are de- (02N)3C6H2.CH2.0 .C6H3(N02)J?) were reported
scribed in Beil 6,449,450, (223) & [425] prepd by nitration of either 4-nitrobenzyl-2,4-di-
Benzyhnononitropherzyl Ether, C6H5.CH2.0.C6- nitrophenyl ether(mp 207-8°) or Z-nitrobenzyl
H4 .N02; mw 231.24, M 6.06~. Three isomers are -2,4 -dinitrophenyl ether(mp 1880), using mixed
described in Beil 6,433,(220)& [412] nitric-sulfuric acids. A product of mp 146 °(dec),
Mononitrobenzyl-rnononitropbenyl Ether, 02 N. Ce- but not further identified, was obtd on recrystn
H4.CH2.0.C6H4.N02; mw 274.23, N 10.22%. from chlf. Attempts to prep a hexanitro deriv
Three isomers are described in Beil 6,449,451 & led to formation of decompn products
[425] Refs: l) Beil- not found 2)H.Ryan & J .Keane,Sci-
Berzzyl-dinitropbenyl Ether, C6 H5 .CH2.0.C6H3- ProcRoyDublinSoc 17,287(1924) & CA 18,1654
(N02)2; mw 274.23, N 10.22%. Two isomers are (1924)
described in Beil 6,433 & [412] Hexanitro Derivative of Benzylphenyl E tber, C, ~-
Mononitrobenzyl.dinitrophenyl Ether, 02N:CGH4- HeN6013, was not found in Beil or in CA thru
CH2.0.CGH~(N02)2; mw 319.23, N 13. 16%. TWO 1956
isomers are described in the literature: 4-Nitro-
benzyl-2,4-dinitropb enyl Ether, Orn-yel ndls Benzyl Picrate. See Benzyl-2,4,6-trinitrophenyl
(from benz), mp 198-201°(Ref 2) and 4-Nitro- Ether under Benzylphenyl Ether
benzyl-2, 6-dinitropbenyl Ether, ndls(from benz),
mp 1376(Ref 1). Other props and methods of Benzylpyridine and Derivatives
prepn are given in the Refs Benzylpyridine (called 2-, 3- or 4-Benzyl-pyridin
Refs: l)Beil 6,451 2)Beil 6,451& [425] in Ger)~ Cl ~H, ,N; mw 169.22, N 8.28%. This
2,4.Dinitrobenzy1.4.nitrophenyl Ether, (02N)a- compd exists in 3 isomeric forms:
C~H3.CH2.0.C6H4 .N02; mw 319.23, N 13.16%; H$-N=C.CH2.C6H5 HC-N=$H
almost COI ndls(from NB), mp 202-204°; readily H?-CH=CH H?-CH=C.CH2.C~H5
sol in warm toluene; S1 sol in acet or glac AcOH; 2(or a)-Benzylpyridine 3(or ~)-Deriv
insol in w or ale; other props and method of prepn
 I

B 100

4)A.J.Nunn & K.Schofield,JCS 1952,587-8 & CA

H$-N=$H
HC-$=CH 46,9565-6(1952)
Trinitrobenzylpy ridine, C, ~HaN406- not found in
CH2.CeH5
Beil or in CA thru 1956
4(or y)-Deriv
The2-Derivis acitron-likeliq, bp 276° at742mtq 1-(2,4,6-Trinitrobenzyl)pyridiniumAzide,

d 1.054 at 20 °(Ref 1); 3-Detiv, ndls, mp 34°, bp [(02N)3C6H2.CH2 .C5H4NI.HN,;

287-8° at 760mm(Ref 2) and 4-Deriv, Iiq, bp mw 347.25, N 28.24%; orn-red polyhedra with brn
287° at 742mm, d 1.061 at 20 °(Ref 3). All derivs streaks, mp 99°(dec); was prepd by adding solid
form tryst, colored salts and addn compds, such Na azide to a coned aq soln of trinitrobenzyl pyr-
as picrate, nitrate, etc. Their props and prepn are idinium bromide. Its expl props were not investi-
given in the Refs gated. The Nitrite salt, [(02N)3C6HZ.CH2 .C5H4-
Refs: l)Beil 20,425,(158) & [270] 2)Beil 20, N]. HN02; mw 351.23, N 19.94%; yel-red plates,
426 & [272] 3)BeiI 20,426,(158)& [272] turning very dk-red after long exposure to light,
4)C.H.Hands & F. R.Whitt,JSCI 66,407-9(1947) mp 88 °(dec), was also prepd, but its expl props
& CA 42,3754(1948) (Describes a pilot plant were not investigated
for the prepn of mixed benzylpyridine isomers) Re/s: l) Beil- not found 2) F. Kr6hnke,ChemBer
Morzonitroberzzy lpyrr”dine, 02N.C6H4.CH2. C~H4N; 88,859-60( 1955) & CA 50,4960(1956)
mw 214.22, N 13.087.. The tollowing isomers are Benzylsuccinic Acid and Derivatives
described in the literature: 2-(2-Nitrobenzy l)-pyr- Benzylsuccinic Acid(called Benzylbernstein-
idine, yel oil, bp 160-170° at 0.4mm(Ref 5); s;ure; +l?henyl-propan-dic arbons:ure-( 1.2) or y
2-(3. Nitrobenzyl)-py ridine, yel oil; isolated as -Phenyl-brenzweins:ure in Ger), C6H5.CH2.CH-
the picrate, mp 157-8 °(Ref 4); 2-(4 -iVitrobenzyl) (COOH).CH2.COOH; mw 208.21; ndls or lfts
-pyrr”dirze, pale yel ndls(from dil ale), mp 81°(Refs (from w), mp 160-10. Other props & prepn are giv-
1,2,4 & 5); 3-(4-Nitrobenzy l)-pyridine, ;oI prisms en in Beil 9,877(384) & [628]
(from ale), mp 88°(Refs 1 & 2); 4-(2-Nitrobenzyl) Benzylsuccinyl Diazide (called Benzyl-bernstein-
-pyridirze, pale yel oil, bp 160-170° at 0.4 to O.6 s~ure-diazid in Ger), C6H5 .CH2 .CH(C0.N3).CH2 -
mm(Ref 5); 4-(3 -Nitrobenzyl)-pyridine, obtd with C0.N3; mw 258.24, N 32.55%; lt yel oil(from eth),
other isomers, but isolated as the picrate, mp expl on heating in a flame; was prepd from benzyl-
156-7 °(Refs 1 & 2); and 4-(4-Nitrobenzy l).pyr- succinyldihydrazide, Na nitrite anti dil HCI as de-
idine, prisms(from dil ale), mp 74°(Refs 1,2,3 & scribed in Ref 2
5). All mononitro derivs form salts and addn Refs: l) Beil- not found 2) T. Curtius & W. Sand-
compds, such as hydrochloride, nitrate, picrate, haas,JPraktChem 125,105(1930) & CA 24,3231
etc. Their other props and methods of prepn are (1930)
given in the Refs Morzonitro-C1 ,H, , NOe, Dinitro-C, , H, oN20~ and
Re/s: l)Beil 20,[271,272] 2)F.Bryans & F.L. Trinitro-C, , H9N30 ,o-Benzylsuccinic Acids were
Pyman,JCS 1929,551-2 3)C.H.Hands & F.R. not found in Beil or in CA thru 1956
Vhitt,JSCI 66,407(1947) & CA 42,3754(1948)
4)K.Schofield,JCS 1949,2411 & CA 44,2966(1950) Benzyltoluidine and Derivatives
5)A.J.Nunn & K. Schofield,JCS 1952,5s6-8 & CA BenzyltoIuidine (called Tolyl-benzylamin or Methyl
46,9565-6(1952) -phenyl-benzylamin in Ger), C6H~.CH2.NH.C6H4 -
Dinitrobenzylpyridine, (OZN)2C6H3.CH2. C5H4N; CHs; mw 197.27, N 7. 10z. Three isomers are
mw 259.22, N 16.21%. Two isomers are described listed in Beil 12,1033, (4s2) & [551,552]. Detail-
in the literature: 2-(2, 4-Din itrobenzyl)-p yrz”dine, ed description of their prepn is given in OrgSynth
yel prisms(from ale), becomes blue to violet on 21,108-9(1941)
exposure to light but turns yel again on storage Nitrosobenzyltoluidin e, C ,4H, ~N20; mw 210.27,
in the dark or in soln, mp 91-3 °(Refs 1,3 & 4); N 13.33%. Four isomers are described in Bei! 12,
and 4.(2, 4-Dinitrob enzyl)-p yridine, yel prisms 1033,1034,1071 & [5731
(from ale), mp 80-81 °(Ref 1 & 2). Both isomers Mononitrobenzyltoluidirze, C, ~H ,4N202; mw
form salts and addn compds, such as the picrates. 226.27, N 12.38%. Three isomers are described
Other props and method of prepn are given in the in Beil 12,1033,1078 & [577]
Refs Dinitrobenzyltoluidirze,C , ~H1 ~N304; mw 287.27,
Re/s: l)Beil 20 [271,273] 2)A.E.Tschitschibabin
N 14.63%. Three isomers are described in Beil
(A. E. Chichibabin) et al,Ber 58, 1587(1925) 3)K.
12,1034,1089 & [552]
Schofield,JCS 1949,2411 & CA 44,2966( 1950)
 B 101

Trinitrobenzyltoluidine, C, ~H12N406; mw 332.27, prepd

N 16.86%. Two isomers: (2,4,6- Trinitrobenzyl)-o Refs l)Beil- not found 2)T.Curtius & K
- toluirfine, orn-yeI ndls, mp 140° and (z, 4, 6-Tri- Raschig,JPraktChem i25,466( 1930) 3)R.H.WileY
et al,JOC 21,191(1956) & CA 50,15517(1956)
nitroberzzyl)-p-toluidine, brn ndls, mp 122° are
Azido. C3H8N6 and Diazido- C9H7N9 derius were
described in Beil 12,(468)
not found in Beil or in CA thru 1956
Tetranitrobenzyltoluidine, C ,4H,, N50*; mw
Morzonitro- C9H8N402, Dinitro, CgH7N504 and
377.27, N 18.56%, OB to C02 -108. lj%.
Trinitro- benzyltriuzoies C9H6N606, were not
The folIowing isomer is described in the literature:
found in Beil or in CA thru 1956
N-(3’ -Nitrobenzyl)-N, 2, 6-trinitro-p-t ohidirze or 3
1.(4’.Nitrobenzyl)3,5.dinitro.sym.tirazole, was
-Nitrobenzyl-(4-m ethyl-2,6-dinitropbeny [)-nitra-
prepd and described by N. K. Sundholm et al in
mine, 02 N. C6H4.CH2.N(N02) .C6H2(N02)2.CH3;
Conf Progress Rpt of Naugatuck Chem Div of
COI trysts, mp 167°(evoln of gas or expln); easily US Rubber Co, 15 Ott 1949-15 Dec 1949(NOR~
sol in acet or boiling AcOH; less-sol in benz; SI lo121),p 7
sol in alc or chlf; v S1 sol in eth or petr eth; was
prepd by nitration of 3-nitrobenzyl-4 -methylaniline Berclavite B. An aluminized
expl: AN 79.5, Al
with nitric acid(d 1.46)(Ref 2,pp 1061 & 1066) 5, NG 5, cellulose 5, DNT 5 & NC(12%N) 0.5%,
Pentanitrobenzyltoluidine, Cl ~H ,0N60 ,.; mw It has been claimed that its power as measured
422.27, N 19.90%, OB to C02 -87.1%. The by CUP is 125( PA= 100)(See Vol l,p A IX)
following isomer is described in the literature: Refl L. M~dard,MAF 22,596(1948
N-(2’,4’-Dinitrobenzyl)-N, 2, 6-trinitro.p-toluidine
or 2’, 4’-Dz’nitrobenzy l-(4-m etbyl-2, 6-dinitropb enyl) Berdanka(Berdan rifle). A cal 10.7mm, one-shot
-nitramine, (02N)2CeH3.CH2. N(N02).C~H2(N02)2, breech-loading rifle with a bolt system magazine
CHa; COI trysts, mp 144°(evo1n of gas or expln); developed in the 1870’s by the Amer General
v sol in acet, benz or chlf; sol in warm AcOI-I; Berdan and adopted in a modified form by the
less sol in ale; v S1 sol in eth or petr eth; was Rus Govt for the Armed Forces. The weapon
prepd by nitration of 4’-nitrobenzyl-(4-methyl-2, proved to be so good that it was used for many
6-dinitropheny1 )-nitramine with mixed nitric-sulf- years. Although it was replaced in the regular
uric acid(Ref 2 ,p 1060) Army ca 1891 by a 5-cartridge magazine firearm
i?e/.s: l) BeiI- not found 2) P.van den Berg,Rec developed by Mossin & Nagan, the so-called
55,1060,1061,1066(1936) & CA 31,2 179(1937) trtikblineynrzya virztovkcz(three-line rifle cal
7.62mm), the Berdanka was used by irregular
Benzyltriazole and Derivatives troops(opolchentsy) as late as WWI and perhaps
Benzyltriuzole, C~H9N3; mw 159.19, N 26.40%. later. The cavalry version of Berdanka was used
This compd presumably exists as benzyl derivs for training in military schools
of the isomeric, heterocyclic triazole, for examplei Re/s: 1)W. W. Greener, ‘The Gun and Its Develop-
N=CH ment” ,London( 1885), 135 2)W.H. B. Smith, ‘NRA
N=N
/ Book of Small Arms”, Harrisburg,Pa, 2(1952),345
C6H5.CHZ.N and C6H5.CH .N’ I
\l CH=N 2\ 3)Dr M. M. Kostevitch,Buenos Aires, Argentina;
CH=CH
l-Benzyl-sym(or 1,2,4) l-Benzyl-vic(or 1,2,3) private communication 1954)
-triazole -triazole
Berg(Explosive), also known as Nitrolkrut, was
Only the l-benzyl-vic-triazole, crysts(from eth at patented in 1876 in Sweden. It was prepd by
-200), mp 61°, appears to have been prepd and re- blending 100 parts of a mixt of NG 94-99 PIUS
ported in the literature. Curtius & Raschig(Ref 2) NC 1-6% with 50-150 ps of nitrates(of K,Na or
prepd l-benzyI-vic-tri azoIe by the re action of Amm) plus charcoal. Nitrated hydrocarbons might
benzyl azide with the methyl ester of acetylene- be used instead of NG
dicarboxylic acid, followed by sapon and decarb- Refi Daniel(1902), 560
oxylatiorr. Wiley et al(Ref 3) prepd the compd di-
rectly and in better yield from acetylenedicar- Berge(Explosive). An expl mixt suitable for blast-
boxylic acid, followed by decarboxylation to 1 ing: K chlorate 61.0, K bichromate 6.1, sugar (or
-benzyl-vic-triazole(77% yield) charcoal) 27.4 & yel wax 5.5%
Although not reported to have been prepd, the Ref: Dr M. M. Kostevitch, Buenos Aires,Arg; pri-
l-benzyl-sym-triazole may be considered the par- vate communication 1954)
ent compd of some nitro derivs which have been
 1

102

Bergenstrom (Explosive). known also as Salite, gradually to a double-bottom vessel provided

was patented in 1878. It consisted of NG 65 & wi~ a stirrer and contg 87.5 ps of finely pulver-
urea nitrate 35% ized AN, preheated to 80°. The resulting mixt
l?efi Daniel( 1902),699 was cartridge while still hot
In later compns, the mixt DNPh-aniline was
Berger (Explosive). An ammonal-type expl, pro- replaced by mixts of aromatic nomo-and di-nitro
posed ca 1905 as a filler for projs: AN 86, stear- compds
ic acid 8 & Al 6% Refi Daniel(1902),64
Refi Dr M. M. Kostevitch, Buenos Aires; private
communication( 1954) Bergmann.Junk Test(B-Test). The original
test, designed by Bergmann & Junk(Ref-l) for
Berger Mixtures are smoke-producing compns, in- testing stability of NC and propellants, was
troduced by the French, consisting of finely di- modified during WWI by Mayrhofer(Ref 2) and
vided Zn in CC14 mixed with other ingredients. later by Meerscheid-Hullessem( Ref 4). The test
On ignition of such mixtures, Zn decomposes the has been widely used in Europe and to some ex-
CC14 with the formation of ZnC12 as a vapor. On tent in the US
contact with cool air, the vapor condenses and Following is a brief description of the proced-
on combining with moisture a white cloud is form- ure as used for NC:
ed(Ref 1). The compn of the Fr Berger pyrotech- a) Weigh at least two 2.02g samples of NC in
nic mixt listed by Pepin LehalIeur(Ref 2) is: Zn tared weighing bottles(provided with ground glass
dust 15, ZnO 20, Ca silicide 15, tetrachloroeth- stoppers) and dry them at 100* 1° for 80 reins
ane 40, & Na chlorate 10% with stoppers open
The so-called American Mixture, listed by Mar- Note: In testing double-base proplnts same size
shall(Ref 1), consisted of Zn dust 34.6, CC14 samples as above can be used, while for single
40.8, NaCl 9.3, Amm chloride 7.0 & Mg carbon- -base proplnts samples as large as 5g are some-
ate 8.3% and was used in the form of candles. It times required
was cheaper but less effective than smoke-pro- b) Stopper the bottles, cool in a desiccator and
ducing mixts based on phosphorus reweigh
Another mixt which contained neither Zn nor c) Transfer the contents of each bottle as quick-
CC14 was also called 13erger Mixture. Its compn ly as possible(to avoid absorption of moisture
was: pitch 29.2, saltpeter 47.4, borax 10.6, Ca from the air) to special cylindrical glass vessels
carbonate 4.9, sand 4.0 & sulfur 3.9%. It was (see Ref 1), each provided with a ground-glass
cheaper but less effective than the above Amer- neck which can be closed with a stopper attach-
ican Mixture ed to an absorption tube contg ca 25ml of fresh-
Refs: I)Marshall 3( 1932,199 2)Pepin Lehalleur ly distd water which serves to absorb the fumes
( 193 5),470 of nitrogen oxide formed
d) Heat(behind a light barricade) the vessels with
Berges, Corbin et Cie a The name of the
Chedde. attached absorption tubes in a special bath which
French firm who manufd Cheddites for many years is provided with wells(to accommodate the cylin-
drical vessels). The bath is filled with a mixt of
Bergmann, Emil (1857-1922). A Ger scientist spe- glycerin-water(4: 1), which boils at 132t0.2°
cializing in expls and proplnts. In collaboration Note: The B-J- apparatus was manufd in England
with Junk, he developed a test for stability of by Callencamp, London. The bath was similar to
NC & proplnts. Was director of the Chemisch-tech- the one described in ASTM Standards,Part 11
nische Reichsanstalt ( 1946),Test D301-33, p 1714
Refi H. Kast,SS 18,37-9(1924) (Obituary and bio- e)After 2 hours heating, remove each vessel and
graphy) leave it on a rack to cool. As the ensemble con-
tinues to cool, the water is drawn from the ab-
sorption tube to the cylindrical vessel thus wet-
Bergmann Explosives, patented in Germany be-
ting the NC and dissolving any nitrogen oxides
ginning 1893, existed in several modifications. absorbed by the NC as well as any accumulation
The original compn was prepd by melting together on the walls of the vessel
8.3 parts of DNPh (or DNCrs) & 4.2 ps of aniline f)Remove each absorption tube and rinse it with
(toluidine or naphthylamine) and adding this melt distd w into the cylindrical vessel until the 50ml
 B 103

mark is nearly reached PETN+ 1% RDX 0.07, PETN+O. 1% Nitropropane

g) Stopper the vessel(with a glass stopper), shake 0.01 and PETN+ 1% Nitropropane 0.04
it until all NC is dislodged from the bottom and Aubertein(Ref 2,p 120) gives BN for PETN
add distd w to the 50ml mark equal to 0.03
h) Filter the contents into a glass-stoppered bot- Re/s: l)G.Bourjol,MP 35,83-7(1935) & CA 50
tle and det nitrogen oxides as NO by the Schultze 1507(1956) 2)P.Aubertein,MP 41, 117 & 120
-Tiemann method, which is described in Ref 6,pp (1959) 3)P.Aubertein,MP 42,39-46( 1960)(BN of
218-20 and in Ref 7,pp 21-5. The vol of NO(in PETN)
cm3) per lg of sample may be called Bergmann
Value or Bergmann Number(Indice de Bergmann, Bergmann’s Powder. Composed of a mixt of K
in Fr). It must not exceed 5. Oml/lg for NC of 13% chlorate 50, Mn dioxide (pyrolusite) 5 & bran+
N and 4 .Oml/lg for NC of 12%N. The values for woodflour 45%
expls are much smaller(see Bergmann Number) Refi CondChemDict( 1942), 288(not found in later
By multiplying the ml’s of NO by 1.34, the editions)
values in mg’s are obtained. Viggam & Goodyear
(Ref 2a) stated that vaIues in excess of 6.5mg Berg.Roburite Explosive. A mixt of DNB & AN
of NO per Ig of a propeHant indicate instability with or without phenol
Note: Instead of using the Schultze-Tiemann Refi Daniel( 1902),64
method, a simple titration of the above soln(see
h) with alkali might suffice. This titration gives Berkhout Stability Test, designed in the artillery
the amts of nitric and nitrous acids which form as laboratory at Hembrug,Holland, consists in heat-
the result of the reaction: ing samples of NC or proplnts in weighing bot-
2N02 + H20 . HN03 + HN02 tles at 95°, 105° or 110° and noting the loss of
and from this, total amt of N and corresponding wt in a definite period ( such as 72 hrs), as well
NO can be calcd as the time required for evoln of red fumes. The
Re/s: l)E.Bergmann & A. Junk, ZAngChem 17, heating is conducted in a specially designed
982,1018 & 1074(1904) and JSCI 23,953(1904) thermostatically controlled oven. Two models of
2 )F.Mayrhofer,SS 13,425 & 448(19 18) (Modifica- such ovens are described in Ref 1
tion of B-J test) 2a) D. Wiggam & E. Goodyear, (Compare with Jacqu6 Test and with Sy Test)
IEC,AnalEcI 4,74( 1932) 3)Stettbacher( 1933), Refs: l)J.D.Berkhout,SS 17,33-4(1922) & CA 16,
142-3 4)V.Meerscheidt-H~llessem,SS 2$$,192-4 2602(1922) 2)Reilly(1938),85
( 1934); 30,75( 1935) & 31,362-3(1936) (Modifica- Berl,Ernst (born in Austria 1877, died in US 1946).
tion of B-J test) 5) ReiHy(1938),83-4 6)Kast An Austrian-American scientist, an authority on
-Metz(1944),218-20 & 312 7)PATR 140], Rev 1 expls, cellulose, NC, NS, acids, etc. Inventor of
( 1950),19-25 8)P.Aubertein,MP 41, 117( 1959)(A
‘Berl saddlesn, (qv) and Berl pipette. Co
brief description of the B-J test, called “@reuve
-author with Dr Georg Lunge of the ‘Chemisch
de Bergmann-Yunk” in France)
-technische Untersuchungsmethoden”, series
of books published in Germany after WWI
Bergmann Number(BN) (indite de Bergmann, in
Re/s: l)M.Isler,Helv 29,957-73(1946) (Obituary
Fr) is the amt of NO(in cm3) evolved per ig of
& biography with portrait) 2)K.Winnaker,Chem-
sample(such as 5g) heated at 132° for 2 hrs in
IngTech 23, 105-6(1951) & CA 45,4977(1951) (A
the i3ergmann-Junk apparatus(Ref 2). The Fr test biographical sketch)
( %5preuve de 13ergmann-Yunkm) is described as
the CM~thode R6glementaire,Annexe n“l)”, which Berl & Kunze Semimicro Analytical Determina.
tion of Stability of NC is described in Angew
is not available at PicArsn
Bourjol(Ref 1) & Aubertein(Ref 2) detd recent- Chem 45,669-70(1932) & Chim & Ind (Paris) 29,
1y the BN for several HE’s, particularly PETN 607D(1933)
and its mixts with nitrocompds Berl Pipette is a vessel, invented by E. Bed
Following are some BN’s for PETN and its and made by Mr Donat of the USBurMines, for
mixts with other expls, as detd by Bourjol(Ref 1) weighing out small quantities of acids or other
PETN(a!one) 0.01, PETN+O.1% DNT 0.08, liquids. It was tried during WWII in the lab of
PETN+ 1% DNT 0.85, PETN+O. 1% TNT 0.09, Keystone Ordnance Works, Meadville,Pa and
PETN+ 1% TNT 0.70, PETN+O.1% Tetryl 0.05, found to be more convenient to use than the
PETN+l% Tettyl 0.50, PETN+O.1% RDX 0.03, Lunge pipette, especially for weighing semi
 B 104

-mixed and mono-waste acids used in manuf of with a volatile solvent, a single-base proplnt
TNT was manufd at the Newport Torpedo Station,
where Bernadou was in charge of the smokeless
proplnt factory. The same proplnt was adopted
A a few years later by the US Army. This proplnt,
with minor modifications, is still in use
Bernadou was the author of a book entitled
“Smokeless Powder, Nitrocellulose and Theory

I IJ
of Cellulose Molecules”, QliIey,NY(lst edition
c 1901 and 2nd ed 1917) and he traltslated
Rus the book of Brynk on Ballistics
from

Refi Van Gelder & Schlatter(1927),812-21

Procedure: a) clean the pipette by washing it Bernouilli,Daniel (1700-1782). A French math-

first with cleaning soln(K or Na bichromate ematician who, in his ‘Hydrodynamics”, intro-
+concd sulfuric aci~,then with water and duced a concept of elastic gas expansion and
finally with a few ml of acetone. Dry by pas- showed how, by taking into account this ex-
sing compressed air through it b) For filling the ~ansion, it is possible to calculate the travel
pipette, remove both ground glass caps and of a shot in the gun barrel
plunge the tip of the long tube A into the bottle Re/: M. Serebriakov, RInterior Ballisticss ,Moscow
contg the Iiq sample c) Attach to the end of tube (1949 ),translated by Dr V. A. Nekrasoff, Catholic
B a short piece of rubber tubing connected at Univ of America, Contract NOrd 10,260(1954),
the other end to a rubber suction bulb and draw Washington,DC,p 22
liq into reservoir C until it is about half full
d) Remove the tip of A from the Iiq and discon- Bernsteinsaure. Ger for Succinic Acid
nect the suction bulb e)Wipe the tip of A with
tissue paper and replace caps on A & B. Wipe Berta Apparatus is a device used in Italy for
the outside of pipette and weigh the ensemble detn of impact sensitivity of expls. The test,
to O.lmg f) For sampling the acid(or other Iiq) known as Saggio alla B erta is mentioned in Vol
with the pipette, remove both caps and, by tip- l,p XVII of this Encyclopedia under Impact Sen-
ping the pipette toward A, let the acid drip sitivity Test. The values obtained by Berta app
slowly through A into an Erlenmeyer flask contg are similar to those obtained by the USBurMines
distd w g)Straighten the pipette and touch tip app, with 2kg wt. Avogadro(Ref) gives the fol-
of A to a dry spot inside neck of flask h)Re- lowing Berta values, in cm: PETN 38, PA 60
place the caps on A and B and reweigh the en- and TNT 80
semble Refi l)L.Avogadro,MAF 10, 3(1931)
Refi C1ift & Fedoroff,vol 3(1944), Chapter l,p 1.
Barthelot,Marcellin (lf127-1907). A French sci-
Berl Pieces of chemical porcelain,
Saddles. entist who is considered as the founder of mod-
chemical steneware or carbon in the shape of ern thermochemistry. He developed the theory
saddles, used for packing absorption tower$ or of detonation and most of the early theoretical
distn columns. They are m anufd under trade knowledge, pertaining to expls, as well as con-
name “Intalox Saddles” by the US Stoneware Co, tributing to many branches of chemistry other
Akron 9, C)hio than expls. The author of the fundamental work
on expls: %ur la Force des Mati;res Explosives
Bernadou, John B ( 1858-1908). According to Ref, d’apr;s la Thermochimie”, which even today is
Bernadou was a “French and Russian scholar of great value although written nearly 100 years
and Naval Attach: (US) at St Petersburg”. while %0
in Russia he learned about Mendel&v’s smokeless Re/s: l) R. Scholz,SS 3,41 -2(1908 )( Obituary &
propIt made by gelatinization of pyrocollodion brief biography) 2) F. J. Moore & W. T. HaH, ”A
(NC with N= 12.44%) and decided, on his return History of Chemistry”, McGraw-Hill,NY( 1939),
to the US, to introduce it to the Navy. He rais- 272-7 3)H.S.VanKlooster, JChemEducn 28359
ed the N content of NC to ca 12.6% and named -63(1951 )( Bunsen, Berthelot and perkin) 4)M”
it pyrocellulose. By gelatinizing this material De16pine,JChemEducn 31,63 l-4( 1954) (Berthed-
 B 105

ot and industry) 5) E. Farber et al, “Gre at Chem-

Explosive IQ f}Qe VT0
ists”, Interscience,NY( 1961),675 -85 —,
! 1000 i lQOO
Berthelot’s Characteristic Product (Produit Blasting Gelatin(NG 93%) 1164 9511 1640 710 3540
caract~ristique de Berthelot, in Fr) (Charakter- Nitromannite (Nhi) 1099 9508 1520 723 3430

T
istische Produkt des BertheIot, in Ger) and 75%Guhr Dynamite 810 7509 1290 628 3160
Specific Force (Force sp6cifique ou thtorique; Collodion Cotcon(12ZN) 711 7150 730 974 1940
Pression sp;cifique, in Fr)(Spezifische Kraft Black Powder 195 2987 685 285 2770
oder Energie, in Ger) are theoretical expres- Mercury Fulnrinate(MF) 129 4194 410 314 3530
—
sions proposed by Berthelot for characterizing
some properties of explosives and propellants. *f as calcd from V. and T as given by Naoih(Ref 3)
The characteristic product is the expression
QeVo/C, where Qe is the heat of explosion in Marshall(Ref 2) stated that in 1902 Bichel
cal/g(or kcal/kg,Vo is the specific volume of found experimentally that the pressures develop
gaseous products of expln(in cc/g or liters/kg) ed on expln are nearly proportional to Trauzl
calcd to 0° & 760mm Hg, and c is the sum of test values, but the values for QeVo do not show
the mean specific heats of the products of the same degree of correlation. However, this
expln. As the value c is difficult to calculate does not prove conclusively that Berthelot’s
with precision, the product QeVo is often used. characteristic product is without practical sig-
The calcd values for QeVo are betw ca 100000 nificance
and ca 1300000, and it is more convenient to Rinkenbach(Ref 10), using more recent Qe and
express these in terms of QeVo/lOOO V. values, recalcd the characteristic products
Berthelot considered the characteristic pro- and found that for many expls there is a good
duct as a measure of the mechanical work per- relationship betw QeVo and ballistic penduIum
formed by an explosion. This work, called po- test values. This test is considered to measure
tentiel de l’explosif or action expIosive in Fr, the work capacity of explosives. In the following
can also be calcd from the expression QeE, table there are given the product and test values
where E is the mechanical equivalent of heat. for a number of expls
This is given by Muraour(Ref 8,p 76) as 428
Another theoretical value introduced by Ber ~ Ball F’enc
Explosive
thelot is the force .sp&ci/ique (called by Sarrau 1000 (% TNT)
force de l’explosi/). This, designated as f, is
obtained from the expression 1073 VoT/273, Hydrazoi c Acid 1320 161
where V. is the specific VOI and T is the calcd Cyclotetramerhyl ene.tetranitramin e(HMX) 1210 150
absolute temperature o{ explosion Cyclotrimetbylen e-trinitrsmine( RDX) / 1180 150
The force f supposedly represents the pres- Cyanuric Tri aside , 1124 145
sure developed by the detonation of lkg of ex- P entaerythritol Tetranitrate(PETN) 1094 145
pIosive under perfect confinement in a l-liter Nitroglycerin (NG) 1062 140
vessel, provided that the gases produced obey 80/ 20 Amatol 911 130
the Boyle-M ariotte law Nitrocellulose( 13.3% N) 848 125
Note: Kast used the value f for calcg brisance 50/ 50 Am arol 843 122
by his formula B= fdV, where d is the density HexanitrodiphenyI amine(HNDP A) 699 115
of the expl and V is the velocity of deton(see 60% Dynamite 730 114
also under Brisance) Trinitrobenzene( TNB) 714 110
The following table gives the characteristic Picric Acid(PA) 675 109
product, specific force, Qe, V. and T values Trinittotoluene( TNT) 655 100
for some explosives(Ref 3,p 152) 40% Dynamite 424 90
Ammonium Nitrate(AN) 339 78
20% Dynamite 151 70
Lead Azide(LA) , 113 66
1
When plotted, the above data indicate a linear
relationship in accordance with the equation:
%TNT=0.0775QeVo/1000 + 58.5
 B 106

Note: According to the ‘Report on Study of of a cylindrical column is detonated at one end,
pure Explosive Compounds” by A. D. Little,Inc, there is immediately created a detonation wave
Part 111,367,405(1950) and Part IV, 576(1952), which is propagated through the expl. This wave
the correlation betw the Berthelot characteristic is regarded by B as a recurring cycle of transfer-
product and ballistic mortar value is not as red and released energy having four phases:
good as that betw equation of state(PV= nRT) Phase 1. Transformation of mechanical to ca[-
and ball mortar test value. While this latter cor- orz”fic energy. A portion of the mech energy of the
relation is applicable to materials contg metal- layer which was detond is instantly converted
lic elements, this is not true with respect to into calorific energy in the adj scent layer. The
the correlation betw Berthelot’s product and portion of mech energy which is not converted
ball mortar test value to heat becomes the actual vehicle through which
In addition to the linear relationship betw the the work is accomplished
characteristic product and explosive power val- Phase 2. Transformation of calorific to chemical
ues of high explosives shown above, there is energy. Part of the heat released in the 1st phase
a similar relationship betw the characteristic is consumed in the chemical decompn of the next
product and ballistic potential values of proplnt immediate layer of expl and thus releases the po-
compns(Ref 11). The ballistic potential value of tential energy of that layer. The remainder of the
a compn may be expressed as either specific im- calorific energy will be spent in the acceleration
pulse or velocity values obtained by tests in and reinforcement of the them action. A consider-
cannon. Illustrative of this are the following data able amt of kinetic energy is developed at this
stage
Composition QeVo/lOOO Sp Imp,lb see/lb Phase 3, Transformation of chemical to calorific
energy. A complete conversion of potential energy
M-13 796 242 released in previous phases to kinetic energy(which
Pyrocellulose 758.5 231 is largely calorific) takes place
M-1 706 213 Phase 4. “’Transformation of calotific to mechanical
energy. As result of previous actions, a consider-
Note: Propellant M-1 consists of NC(13.15%N) able VOI of gas is released and as the molecules
85, DNT 10 & DBuPh 5% with added ?lPhA 1% & of it are in an extremely active state of molecular
K sulfate 1%; MG13 consists of NC(13.15%N) vibration, they are manifesting energy in a mechan-
57.3, NG 40.0, EtCentr 1.0, DPhA 0.20 & K sul- ical form. Since all these transformations are ex-
fate 1.5% with added Pb stearate 0.15% & car- tremely rapid and the losses due to radiation and
bon black 0.05% conduction of heat are low, the efficiency of this
Re/.s: l)M. Berthelot, “Explosives and Their last phase is very high
Power”, Ahrray, London( 1892), 30-4 2)MarshaIl Refs: l)M. Berthelot, “Explosives and Their Power”,
2( 1917),467-9 3)Nao(im, NG(1928),152 4)Pas- J. Murray, London( 1892),88 2)Colver( 1918),596-8
cal(1930),21 & 28 5)Vennin, Burlot & L6corch6
(1932),53 6)Pepin Lehalleur(1935),40-50 Berthold der Schwarze. A Ger monk, living in the
7)Davis(1943), 210 8)Muraour( 1947),70-6 14th century, to whom is usually ascribed the in-
9)Stectbacher(1948), 110 10)T’m.H.Rinkenbach, vention of firearms using black powder as a propel-
private communication(1960) 1ant
Refs: l)F.M.Feldhaus,SS 1,413-15(1906) 2)0.
Berthelot Powder.Under this term was known a Guttmann,SS 3,218(1908) 3)Stettbacher(1933 ),4
rather unstable expl compn consisting of K
chlorate 80, vaseline+paraffin 10 & chalk 10%, Berthollet, Claude Louis (1748-1822). A French
but Berthelot denied invention of this powder scientist who made numerous contributions to them
Refi Daniel(1902),65 istry and the chemical industry. ItI the expls field,
he was first to prep K chlorate(known as ‘Sel de
Berthelot Theory of Detonation, further develop- Berthollet”), Fulminating Silver and Berthollet Pow-
ed by P. Vieille, may be considered as one of der
the most important contributions to the modern Refs: l) F. J.hIoore & W. T. Hall, ‘CA History of Chem-
concept of detonation istry”, McGraw-Hill, NY(1939), 104-8 2)G.Darzens,
Following is a brief explanation of this theory: BullFr 1948, 1066-8( The life and work of Berthollet)
Supposing that a homogeneous expl in the shape 3)E.Farber,Edit, “Great Chemists”, Interscience,

——— —-—..——--—.
.. ... . . .
 B 107

NY(1961), 315-24 BerylIium Sulfate. See under Sulfates. Its use in

smoke-producing compns was patented by J .DeMent
Berthollet Powder. A compn dangerous to handle: USP 2995526( 1961),P 6
K chlorate 75, sulfur 12.5 & charcoaI 12.5%
Refi Daniel(1902),66 BESA Machine Gun. Cal 0.303 was the Brit adapt-
ation of the Czech, caI 7.92mm ZB-53 Model 1937,
Berthollet Salt (Sel de Berthollet, in Fr). Potas- developed at the Brno factory. BESA MG’s were
sium Chlorate manufd by the Enfield Royal Arms Manufacturing
ArsenaI and the Birmingham Small Arms (BSA)
Beryllium (Be) or Glucinum, at wt 9.02, lt grey met- plant. The word BESA is composed of B for Brno,
al, d 1.842, mp 1284° & bp 2767° [Lange(1956)]; E for EnfieId and SA, the last two letters of BSA.
mp 1350° & bp 1530° (ChemRubHdb); insol in cold There were also 15mm BESA guns
w & in nitric acid; S1 sol in hot w with decompn; Refi G. M. Chinn, “The Machine Gun”, USPrtgOff,
SOI in HC1, dil sulfuric acid & in alks. It does not Wash, DC,vol 1(1951),436-40
oxidize at ordinary temp but when heated in the
powder form burns brilliantly in air. It does not re- Beta CelIulose refers to that portion of industrial
act with steam even at a red heat. Can be prepd by cellulose pulps which is sol in cold NaOH of mer-
the electrolysis of a fused mixt of Be chloride with cerizing strength( 17.5-18%) but is pptd on acidifi-
Na or Amm chlorides, or of the fluoride with NaF cation (See also Alpha-Cellulose and Gamma-CeIlu-
in a nickel crucible with a carbon anode. Be was Iose)
discovered ca 1797 in the form of the oxide by Re/: Ott,v 5,part 1(1954),12
Vauquelin as a constituent of the mineral beryl
(emerald) (Refs 1-5) Beta Compounds, such as @-Nitronaphthalene, ~
Sartorius(Ref 6) claimed that Be or its alloys -Trinitrotoluene, etc, are listed alphabetically
added in small quantities to expI compns render under corresponding parent compds
more powerful expl.s than those contg Al, Mg or
their alloys Beta. and Gamma.Ray Spectroscopy is the title of
Boehm(Ref 8) stated that, due to the h~gh heat a book by K. Siegbahn,Interscience,NY(1955)
of combustion of Be(29000 BTU’s vs ca 19000 for
hydrocarbons), it is theoretically possible to use Betaine (Trimethyl Glycine; Trimethyl Glycocoll or
it(or its derivs) as fuels in jets and rockets. The Trimethyl Amino-Acetic Acid), (CH3)3NCCH2.C0.?
idea must be, however, rejected due to the high or (CH,),fi.CH2.C0.b; mw 117.15, N 11.96%, OB
cost ;of Be and its extreme toxicity. Latest info on to C02 -184.4%. Prism s(from ale), mp 293 °(decomp);
toxicity of Be and its compds is given in Ref 10 sol in w & in ale; insol in ether; occurs in plants
Refs: 1 )MeIlor 4(1>23),204-21 2) Gmelin,Syst Nr (usually together with choline) and in some sea
26(1930), 1-80 3)Thorpe 6(1943),13-15(Glucinum) animals. Can be prepd by methyl ation of amino-
4)Kirk & Othmer 2(1948),490-505 5 )J.R.Pattington, acetic acid or by other methods. Betaine has been
‘(A Textbook of Inorganic Chemistry”, Macmillan, used in org synthesis to render various compds
London(1950),771 6)R.Sartorius,MP 34,217-20 water-soluble. For instance, Girard’s reagent(which
( 1952) 7)D.W~White,Jr & J. E. Burke, “The Metal is a deriv of betaine) is used to prepare water-sol
Beryllium”, AmSocMetals,Cleveland,0hio(1955) derivs of insol ketones and aIdehydes(Ref 2,p 510)
8)G. Boehm,Fortune,Dec 1957,p 166 9)C. E. Datwin Betaine forms additive compds with acids and
& J. H. Buddery, “Beryllium’’, Academic Press,NY salts, some of them explosive (See below)
(1960) 10)L.B.Tepper, “Toxicity of Beryllium Re/s: l)BeiI 4,346,(469) & [785] 2)Kirk & Othmer
compo~ds”, EIsevier,NY( 1961) 2(1948),510

Beryllium Acetylide. see VOI l,p 70-R Betaine Additive Compounds with Acids (Explo-
sive) can be prepdby treating betaine with an acid
Beryllium Azide.. Same as Beryllium Diazide rich in oxygen, such as nitric, chloric or perchloric.
In the case of dichrom ate and permanganate addi-
Beryllium Carbide. See Vol l,p A71-L tives, where the acids do not exist in the free
state, the corresponding K or Na salts mixed with
Beryllium Diazide. See Vol l,p A524-R sulfuric acid can be used for treating the betaine:
Eletaine Chlorate, C5H1 ,N02.HC103, wh monocl
 1

B 108

trysts, mp 115° and explg at high temps; sol in w spin around the tube. During this rotary movement
(Refs 1 & 2) the electrons are accelerated(by magnetic induction
Betairze Dicbrorrzate, (C5H1 ,N02)2.H2Cr2.07; red instead of by direct application of high potential
trysts, mp 226-7°, explg at higher temps(Refs 1& as is done in the more conventional types of x-ray
2) units) and when they have reached their maximum
Betaine Nitrate, C5H1 , N02.HN03; wh lustrous energy their orbit is slightly increased so that they
plates; mp 124°, exploding at higher temps; sol in strike a platinum or thoriated tungsten target and
w(Refs 1 & 2) produce x-rays. The rays emerge from the “donut”
Betairze-Nitrogen Oxide, C5H1 ,N02.N203; wh in a narrow cone in the direction which the elec-
trysts, obtained by prolonged action of nitric acid trons are traveling at the time
on betaine under pressure(Ref 2) The magnetic method of acceleration(first stated
Betaine-Nitrogerz Oxide, (C5H, , N02)5.N203; wh in general principle by J. Slepian in 1927) has ex-
trysts, obtained by passing N203 into an ice-cool- tended the range of x-rays indefinitely, the only
ed soIn of betaine in methanol(Ref 2) limit being the size of the machine. The first suc-
Betaine Percblorate, C5H1 , N02.HC104, wh trysts, cessful unit utilizing the magnetic principle was
sol in w; expl(Ref 1) invented and constructed by Dr D. W. Kerst at the
Betaz’rte Permangarzate, C5H1 ,N02.HMn04; vioIet University of Illinois ia 1940. It had a maximum
rhombic trysts, explg on heating(Refs 1 & 2) energy of 2.3 mev(million electron volts). Four-,
Betar’ne Picrate, C5H1 , N02.C6H3N307; lt yel ten- and twenty-mev units soon followed. Tests
crysts(from hot w), rnp 180-1°; expl(Ref 1) with the betatron showed that the best energy for
Re/s: l)Beil 4,(470) 2)H.Stolzenberg, BritP ‘s5736 industrial radiographic use is 20 mev. Manuf of
&5737(1914); CA 9,2313 (1915XThe use of compds these units was soon started by the Allis Chalmers
of betaine with acids rich in oxygen(such as chlo- Company under the supervision of Dr Kerst. De-
ric, nitric, perchloric, etc) as ingredients of expls scription of this apparatus may be found in Refs
compns is recommended. Eg: betaine nitrate 36, 7,8 & 10. Larger and more powerful units have been
NG 25, wheat flour 38.5 & betaine 0.5%] or are under construction for experimental work in
research laboratories
Betaine Explosive Derivatives. Pfeifer et al(Refs From the beginning the betatron was found to be
1 & 2) prepd, in the course of their work on betaine of value as a ‘non-destructive tool in ordnance ap-
and derivs, several percblorates which proved to plications. The first of the 20 mev units was in-
be explosive: stalled at Rock Island ArsenaI for the purpose of
a) C, *H1 ~N02.HC104; wh cwsts, mp 169-70°; expl inspecting heavy gun mountings. A second such
on heating in open flame(Ref l,P 1775) unit was installed at Picatinny Arsenal following
b) Cl , HI ~N02.HC104; wh trysts; mp 196-7°; exp} WWII. This unit has not only been used for check-
on heating in open flame(Ref l,p 1776) ing the internal condition of heavy or bulky metal-
C) [( CH3)3N.CGH4. CH:CCLC0.0HlC104; wh trysts; lic items perraining to Ordnance(up tc 20” of steel
mp ca 280°; expl when heated on a Pt spatuIa(Ref can be penetrated and it is possible to detect a
l,P 1787-8) difference of 1/32” in any penetrable thickness of
d) (C, ~H, ~N204 )C104; wh ‘c~sts; decomp explo- steel), but also for checking the explosive filler
sively on rapid heating in a capillary tube(Ref 2,P of large projectiles for the presence of voids or
foreign material. This has resulted in a wealth of
44)
Re/s: l)p.pfeiffer & G. Haefelin,Ber 55,1769-88 information without destruction of materials being
(1922) 2)P.Pfeiffer et al, Ann 465,20-52(1928) inspected. More recently three 24 mev betatrons
have been installed in eastern and Midwestern
Beta.Ray Autoradiography for the Study of Metals steel foundaries for inspection of armor steel cast-
and Minerals on Microscale is described by A.B. ings before assembIy into army tanks.
Michael et al, JApplPhys 22, 1403-6(1951) In addition to the penetrating power of the x-rays
there are certain other characteristic phenomena
Betatron is an x-ray-producing apparatus consist- encountered in radiography with the betatron not
ing essentially of an electromagnet and a donut found with low voltage x-rays, such as: a) A rela-
-shaped vacuum tube placed between the pole faces tive freedom from scattered radiation. The second-
of the magnet. The supply of eIectrons is released ary radiation will tend to retain direction which the
inside the vacuum tube from a glowing filament and, primary radiation originally had. Hence, no block-
under the influence of the alternating magnetic flu% ing is necessary around an irregular object or be-
 B 109

hind the cassette b) A near absolute sensitivity y. Bettanin’s Explosive. A mixt of dynamite(prefer-
This rnems the size of the minimum detectable flaw ably with 60% NG) 76, K chlorate 18 & oil of pine
with a given film technique does not depend on (tar or rosin) 6%
total thickness of the specimen being x-rayed, but Refi F. P. Bettanin,USP 930030(1909) & CA 3,2753
is independent of the specimen thickness. Another (1909)
phenomena is direct magnification up to 3X with-
out loss of definition or detail. This is due to a Bettermann’s Electric Delay Detonator, patented
combination of fine focal spot and the lack of sec- in 1898, may be considered as the precursor of
ondary scattered radiation. These characteristics modern deIay detonators. A detailed description
of the radiation produced by the betatron frequent- with schematic drawing is given in D aniel( 1902),
ly extend its usefulness beyond the range of con- 66-7
ventional x-ray units
Note: The section on Betatron was prepd in col- Bevatron is a very powerful particle accelerator
laboration with Kathleen G. Sheffield, formerly of installed in 1954 at the Univ of Calif. This machine
PicArsn,Dover,NJ is capable of accelerating protons to an energy of
Re/.s: l)J.Slepian,USP 1,645,304(1927) 2)R. 5 BEV(billion electron volts)
Wideroe,ArkivElektrotech 2 1,387(1928) 3)E.T.S. Refi Anon, Ordnance 38,908( 1954)
Walton, ProcCambridgePhilSoc 25,469(1929) 4)M.
Steenbeck,USP 2,103,303(1937) 5)D.W.Kerst, Beyling, Carl (1871-1938). A Ger engineer special-
PhysRev 58,841(1940); ibid 59,110(1941)& ibid izing in mining expls. Author, in collaboration
60,47-53( 194 1) (Acceleration of electrons by mag- with K. Drekopf, of the book “Sprengstoffe und
netic induction) 6)D. W. Kerst & R. Serber,Phys Z~ndmittel”, Springer, Berlin(1936)
Rev 60,53-8( 194 1) (Electronic orbits in the induc- Re/.s: l)H.Woltersdorf,SS 33,333-4(1938) 2)H.
tion accelerator) 7)D.W. Kerst,AmJPhys 10, No Woltersdorf,Nobel Hefte,Feb 1939, enclo~ed in SS
5,219-24(1942) (The betatron) 8)D.W.Kerst,Rev- 34(1939) betw pp 64 & 65(Carl Beyling, zum
SciInstr 13, No 9,387-94( 1942) (A 20-million-elec- Ged~chtnis)
tron-volt betatron or induction accelerator) 9)H.
W.Koch,D.W.Kerst & P .Morrison,Radiology 40,120 BF (Poudre B de fusil). See under B(Poudre)
-6(1943) (Experimental depth dose for 5,10,15 and Note: Alvaro-Alberto, AnAcadBrasileiraCiencias
20-miHivolt x-rays) 9a)D. W. Kerst,OSRD 1333 or 15, No 1,pp 50- l(hiarch 1943) gives compn of one
PBL 5224(1943) 10)J.P.Girard & G. D. Adams, of these older proplnts analyzed in Brazil: NC
TransAmInstElecEngrs 65,241 -6(May 1946) (AppIi- (12.7%N) 97.3, ether 0.8, ethanol 0.4 & moisture
cation of the betatron to practical radiography) 1.5%
11) H. Hinterberger,SBOe sterAkadWiss,Abt Ha, 156,
No 5-6,299 & 334(1948) (A general theory of the BF-122 & BF-151 are composite polysulfide pro-
betatron) 12)D.W.Kerst et aI,RevSciInstr 21,462 plnts for rocket motors developed by the Thiokol
-80( May 1950) (An 80-mev model of a 300-Mev beta- Chem Corp. Their compn & props are given in conf
tron) 13)M.Het6nyi, “Handbook of Experimental propellant Manual, SPIA/M2( 1959),Unit NOS 570 &
Stress Analysis”, Wi1ey,NY(1950),982 14)R.widr$e , 571
ZVerDeutIng 96(15-16), 450-6(1954) (Verkstoffpr;fung
mit Betatron-R6ntgenstrahlen), translated in GtBrit BFAM (Poudre B, amyl al cool). See under B(Poudre )
by Tech Info & Library Services TIL/T4575(Feb Note: Alvaro-Alberto, AnAcadBrasileiraCi encias
1958) (“Material Testing by .Betatron” ) (numerous 15, NO l,pp 50-l(March 1943) gives compn of one of
refs) 15)P.Grivet,RevGkMIllec 64,239-62(1955) & these older proplnts analyzed in Brazil: NC(12.7%N)
CA 49,11429(1955) “(Review on theoretical Principl- 95.1, amyl aIc 2.0, ether 1.0, ethanol 0.5 & mois-
es and properties of the betatron and synchrotrons) ture 1.4%
16) USNatBurStds Handbook NO 55, “Protection A-
gainst Betatron-Synchrotron Radiations up to 100 BFNL (Poudre B ~ fusil,nitrat~e lav+e). See under
h4ilIion Electron Volts”, USDept of Commerce, B(Poudre)
Washington,DC( 1955 ),52pp 17)Collier’s Encyclo-
pedia 7(1957), lgO(Under Electron and Ion Ac- BFP (Poudre B en paillettes pour fusil de guerre).
celerators) 18) F. Timpl,Technik(B erlin) 12,5 1+18 See under B(Poudre)
541-7 & 612-16(1957); CA S1,16119(1957) & 52,
101(1958) BFP1 (Poudre)(S6rie 389-SL-1931), described by
 B 110

H.hfuraour et al, in MP 35,280(1953), consists of 603,604(283) & [508] of which the following is of
NC(13.2%N) 98.9, DPhA 0.9, & residual solvent importance because it can serve for prepn of expl
(alcohol) 0.2%. It is in the form of square grains higher nitro compds: 4, 4’-Dinitrobibenzyl or p, p’
1.54 x 1.54mm and 0.28mm thick -Dinitrobibenzyl, 02 N. C6H4.CH2. CH2.C6H4.N02.
Pale yel ndls, mp 179-182°. Was first obtained in
BG (Poudre B de guerre destin~e 2 l’arm6e de 1866 by Stelling & Fittig on nitrating bibenzyl
terre). See under B(Poudre) with coned nitric acid(Ref 1). Rinkenbach & Aaron-
son(Ref 3) improved the method by using a weaker
BGC (Poudre B de guerre pour gros c alibre). See acid(d 1.42). Green et al(Ref 2) prepd the dinitro
under B(Poudre) -compd by air-alkali oxidation of p-MNT. Methods
similar to Green’s are described in detail in Refs
BGY. A cast double-base proplnt for rocket motors 4 & 5. 4,4’-Dinitrobibenzyl can serve for the prepn
developed at ABL. Its compn & props are given in of tetra-, penta- and hexanitrobibenzyls
conf Propellant hfanual,SPIA/M2 (1959 ), Unit No 575 Refs: l)Beil 5,6o4 & [508] 2)A.G. Green et al,
JCS 91,2079(1907) 3)W.H.Rinkenbach & H.A.
BHQ. Ditto, Unit No 576 Aaronson, JACS 52,5040-1(1930) & CA 25,508(1931)
4)R.C.Fuson & H. O. House,JACS 75,1325-6(1953)
Biacetylene. Same as Butadiyne & CA 48,3316(1954) 5)OrgSynth 34,35-6(1954) &
CA 49,5401(1955)
Biazole. Same as l,3,4-Oxadiazole Trinitrobibenzyl, C, ~H, , N3 06-not found in B eil
or in CA thru 1956
Biazzi, Mario, of Vevey, Switzerland, is the in- Tetranitrobibenzyl, C14H10N40~; mw 362.25, N
ventor( 1935) and producer of apparatus for contin- 15.47%, OB to COZ -110.5%. The following isomer
uous manuf of expls, such as NG, 13FGDN, Nitro- is known: 2,4,2’,4’-Tetranitrobibenzyl,
benzene, Nitrotoluene, PETN, RDX, etc (02 N)2C6H3 .CH2.CH2.CGH3 .( N02)2; pale yel
Re/s: l)W. Belittler & D. B. Clapp, BIOS Final Rept ndls, mp 168-172°; expl in 5secs at 380° but did
1842k1946) 2)Stettbacher (1948), Advertisement not expl by impact of 2kg wt falling 34”; insol in
at the back of the book 3)J .C. Smith, ChemInds w or ethanol; sl sol in eth or chlf; appreciably
62,929-31(1948) & CA 43,1711(1949) (Biazzi pro- ‘ sol in ethyl acetate, hot benz, toIuene, acetone,
cess for continuous nitration) 4)H. J. Klassen & acetic acid or ethylene dichloride. Was prepd in
J.hi.Humphreys, ChemEngProgr 49,641-6(1953) & 1916 by Braun & Rawicz(see in Ref 1) in 70% yield
CA 48, 1683(1954) (Manuf of NG by the Biazzi con- by nitration of bibenzyl with fuming nitric acid,
tinuous process) 5)Groggins( 1958), 747-9 6)A. with cooling. Rinkenbach & Aaronson(Ref 2) de-
Stettbacher, Explosivst 1959,187 vised a method of nitration with nitric acid which
permitted increasing the yield to 90% or even high-
Bibenzoyl,Same as Benzil er. Attempts to prep the tetra-compd by the use of
nitric-sulfuric mixt gave negative results. Ogata &
Bibenzyl and Derivatives Oda(Ref 3) prepd the 2,4,2’,4’-tetra-nitrobibenzyl
Bibenzyl; sym-Dipbenyletbane or a, :“ ‘-Dipbenyl- by nitration of bibenzyl or of 2,2‘-dinitrobibenzyl.
ethan e (called a. /3 -Diphenyl-~than or Dibenzyl in B1 att & Rytina(Ref 4) prepd it by nitrating with
Ger), 100% nitric acid either 4,4 ‘-dinitrobibenzyl or bi-
~CH-CHN a1 ~CH-CHx berrzyl. Rinkenbach & Aaronson(Ref 2) found that
HC, C-CH#H2-C, CH. Its prepn 2,4,2 ‘,4 ‘-tetranitrobiben zyl could not be initiated
CH=CH’ CH=CH’
by 0.4g MF or by the combination of 0.23g MF &
and props are given in Beil 5,598,(280) & [506] 0.40g Tetryl when tested in a sand bomb. However,
Note : Y. Ch.Chatovedi,IndianP 44569(1952) & CA when 0.23g MF with 0.40g RDY was used for ini-
47,6443(1953) patented a method for the manuf of tiation complete deton took place. The sand test
bibenzyl by bubbling HCI gas through a refluxing value of tetranitrobibenzyl was found to be 70% of
mixt consisting of dry benzene, dichloroechane and that of TNT
Al-Hg alloy turnings Re/s: l)Beil 5,(285) 2)W.H. Rinkenbach & H.A.
Mononitrobenzyl, C6H5. CH(N02).CH2. C6H5. One Aaronson,JACS 52,5041(1930) & CA 25,508(1931)
isomer is described in 3eiI 5, 603 3)Y.Ogata & R. Oda,BullInstPhy sChemResearch
Dinitrobibenzyl, C ,4 H12N204; mw 272.25, N (Tokyo) 21,238(1942) &CA 43,7918(1949) 4)A.H.
10.29z. Several isomers are described in Beil 5, Blatt & A. W. Rytina, JACS 72,404(1950) & CA 45,

1 ——.. -— —.——.—..—.....——-
 B 111

1081(1951) CA 45,1081(1951)
2,4,6,2',4'.Pentanitrobibenzyl, C14H9N5010; mw
407.25, N 17.2%, OB to C02 -88.4%. Pale yel BIC. A cast double-base proplnt, developed at
Crysts, mp 187-8°. Was obtained together with ABL. Its compn & props are given in conf PropeI-
hexanitrobibenzyl by Blatt & Rytina(Ref 2) on Iant Manual,SPIA/M2( 1959),Unit No 577
treating tetranitrobibenzyl with nitric-sulfuric acid
and oleum. Its expl props were not detd Bicarbamyl Azide (caHed Hydrazodicarbona zid or
Re/.s: l)Beil- not found 2)A.H.Blatt & A. W. RY- Hydrazin-N.N’-dicarbonsiiure, in Ger),
tina,JACS 72,404(1950) & CA 45,1081(1951) N3.C0.NH.NH.C0.N3; mw 170.10, N 65.88%, OB
2,4,6,2’,4’,6'.Hexanitrobibenzyl or 2,4,6,2’,4’,6’ to Coz -28.2%. Crysts, mp 150-2° (with vigorous
.Hexanitrro.sym.diphenylethane, evoln of gas); expl violently on rapid heating
(02N)3C6H2.CH2. CH2.C6H2(N02)3; mw 452.25, above the mp. Very sol in eth; easily SOI in ale,
N 18.58%, OB to C02 -70.8%. PaIe yel trysts, mp acet or hot ethylene bromide; S1 sol in w; insol in
213-218°. Will(?lef 2) claimed that he prepd the chlf or benz. Can be prepd in small yield by di-
compd with mp 212° either by nitration of dinitro- azotizing bi(carbamyl) hydrazide. It is a primary
bibenzyl or by oxidation of u-TNT, but he gave no type expl similar to LA and AgA; impact sensi-
detailed procedures. Rinkenbach & Aaronson(Ref tivity 70cm using 100g wt, vs 80-85cm for LA and
3) obtained it in a very small quantity [together initiating ability is approx the same as that of LA
with a large amt of 2,4,2’,4’ ,6’-pentanitro-a-hydrox- (0.2 5g required to deton lg of molten TNT)
ybibenzil, (02 N)3C6H2.CH2.CH(OH) .C6H3(N02) ~, Re/s: I)Beil 3,(6o) & [102] 2)T.Kesting, Ber
also called a-2 ,4,6 -trinitrophenyl-~ -2,4-dinitro- 57 B,1321-3(1924) & CA 19,245(1925)
phenyl-hydroxyethane] when ‘they nitrated the pre-
viously sulfonated tetranitrobibenzyl by a rather Bicarbite or Bikarbit. A dynamite consisting of
complicated procedure. Mecir(Ref 3a) claimed to NG 15, bicarbonate 50 & NaCl 35%(Ref 1). Its
have prepd the hexanitro-compd by treating a-TNT props are described in Ref 2
with an aq soln of Na sulfite R e/s: l) Beyling & Drekopf( 1936), 145 2)PATR
Parkes & Farthing(Ref 5) prepd the hexanitro 251O(PB No 161270) (1958),p Ger 11
compd by passing dry air for 5 hrs through a mixt
of 5g TNT & 5g Na carbonate in 150ml water, Bicarbonates. See under Carbonates
heated on a water-bath. The mixt was then cooled,
centrifuged and the solid(6g) was dried in a vacuum Bichel,Christian E. (1857-1914). A Ger scientist
oven over coned sulfuric acid. Extraction with and artillery officer who specialized in industrial
benzene in a SoxhIet left a residue(2 .4g) of finely expls. Inventor of the BicheI Bomb, several expl
divided black solid which exploded on heating(its compns and author of several papers on physical
compn was not established). The benz extract was testing of expls and of the book: {’Untersuchungs-
evaporated to ca 40ml and then left in a vacuum methoden fh Sprengstoffe”, W. Ernst, Berlin(1905)
over coned sulfuric acid. White ndls formed at the Refi W. K6nig,SS 10,73-4(1915 )(An obituary)
bottom of the soln and then TNT on the waHs of
the dish. The white ndls were separated(0.2g) and Bichel Bomb or Bichel Pressure Gage. See p VIII,
recrystallized from toIuene. The purified material under Physical Tests in Vol 1 of this encyclopedia
had mp 216-17°. Blatt & Rytina(Ref 6) prepd a
small quantity of the hexanitro-compd with mp 213 Bichel Calorimetric Bomb is a heavy-walIed cylin-
-15° by prolonged nitration of pentanitrobibenzyl drical steeI bomb with a removable cover used for
(previously obtained by nitration of the tetranitro detn of the amt of heat liberated during an expIn
-compd) with nitric-sulfuric acid mixed with oleum (heat of expln). The original bomb had a 30-liter
BIatt(Ref 4) stated that hexanitrobibenzyl is capacity and was intended for use with a 10Og
less powerful and less brisant expl than PA sample. Later models of the bomb were smaller
Refs: l)Beil .5,(285) 2)W.Will,Ber 47,704(1914) and 10g samples were used
3)W.H.Rinkenbach & H. A. Aaronson,JACS 52,5044 A different kind of Bichel Bomb, known also as
-5(1930) & CA 25,508(1931) 3a) J. Mecir,Chim & Bichel Pressure Gage has been used for detn of
Ind(Paris) 1933, Special No,pp 952-9 & CA 28,645 pressure of exph-t and for collecting and examin-
(1934) 4)Blatt,0SRD 2014(1944) 5)G.~.Parkes ing products of expln
& A. C. Earthing, JCS 1948,1277 & CA 43,592(1949) Re/s: l)Stettbacher(1933 ),84 2)PATR 2700(1960]
6)A.H.Blatt & A.?7.Rytina,JACS 72,404(1950) & Vol l,p VXII
 112

Bichel Explosives. The following expl mixts were company manufactures many varieties of fuses,
patenredby Bichel: a)Mixts of nitric acid and among them the detonating fuses, such as Cordeau
kieselguhr packed in plastic cartridge s(Ref l,P 67) Bick/ord, a lead tube filled with TNT, and Pn”ma-
b) Mixts of hydrocarbons(preferably oils) satd with cord Bick/ord, a tube of waterproof textile filled
28-30% of pulverized sulfur, with nitrates, chlor- with desensitized PETN(see also Fuses)
ates, NG, nitromannite, etc; such as:sulfurated Re/s: l)Daniel(1902),428-33 (M~ches de sfiret~)
turpentine 3 parts and NG 10ps or sulfurated tar 2)Marshall 1(1917),38; 2(1917) &3(1932 ),165-8
oil 10Ps, nitrocumol 5ps and Na nittate 90-100ps 3)Davis(1943),11-14 4)Blasters’Hdbk( 1952),87-90
(Ref l,p 68) c)Blasting expl: AN 86, TNT 8 &
flour(or starch) 6%(Ref l,p 68) d) Blasting expl: Bickford Igniter or Igniter Fuse. When working in
TNT 85, Iiq oleoresin(such as storax) 4.5, DNT gaseous mines, it is important not to use an open
10 & collodion cotton 0.5%(Ref 2) flame for igniting the safety fuse, but to use some
Re/s l)Daniel(1902),67-8 2)C.E.Bichel, USP flameless device. One of the older devices was
896887(1908) & CA 2,3283(1908) the E?ick/ord Igniter, which consisted of a metallic
tube of tinned iron or steel to be fitted to the free
Bichel Pressure Gage. See Bichel Bomb,p VIII, end of the fuse(the end to be ignited). This tube,
VOI 1 of this Encyclopedia closed at one end, contained a small glass cap-
sule with coned sulfuric acid and a pellet of K
Bichel Recording Pressure Gage. Same as above. chlorate-sugar mixt. By pinching the metal tube,
See also Marshall 2(1917 ),445-7 the capsule was broken and the liberated acid
ignited the chlorate-sugar which in turn ignited the
Bichromafes. See Dichromates under Chromates black powder in the core of the fuse. When the fire
and Dichromates reached the other end of the fuse, a spit of flame
shot into the blasting cap and this detonated the
Bickford Fuse or Miner’s Safety Fuse is a device explosive(see also Fuse Lighters)
patented in 1831 by William Bickford of Cornwall, Re/: Marshall 2(1917),538
EngI and, for firing blasting charges safely. It re-
placed older methods of firing, which consisted Bickford & Smith’s Primary Mixture, patented in
either of igniting a train of black powder laid up 1898 consisted of Na tungstate, Sr nitrate, Sb
to the blasting charge or of using a quill(or rush) sulfide, K chlorate, graphite and pptd Cu of Ag
filled with black powder as an igniter. As the time Refi Daniel(1902),70
taken by these older devices to burn was very
uncertain many accidents took place during firings Bicresol and Derivatives
because the personnel did not withdraw from the Bicresol; Dibydroxydimetby lbipbenyI or Dihydmxy-
danger zone in time. The 13ickford fuse did away bitolyl(Dicresol) (called Dioxy-dimethyl-diphenyl
with this uncertainty because the rate of burning in Ger), H3C\ CH~
is definite /
CH.CH
/6363, ” Several isomers
The original Bickford fuse consisted of a central HO OH
thread surrounded by a core of black powder en- are described in Beil 6, 1009,(492) [973-4]
closed within a tube of woven threads, such as Monorzitrobicresol, C ,4H ,3N04. One isomer is de-
jute. This could be surrounded by various layers scribed in Beil 6,101o
of textile and, in order to make the fuse waterproof Dirzitrobicresol, C ,4H ,2 N206. One isomer is de-
it could be varnished on the outside. Sometime be- scribed in Beil 6,1010 & [974]
fore 1~0 a guttapercha-covered fuse, designed for Trinitrobicresol, C, ~H, ,N308 - not found in Beil
underwater work was adopted. Since then, many or in CA thru 1956
other modifications have appeared including a Tetranitrobicresol, C ,4 HION4010; mw 394.25, N
fuse cased in metal, the so-called Collie~ Fuse, 14.2893. One isomer: 2,6,2’, 6’-Tetranitro-4,4’-bi
which emits no spark s(1886), and the Instant Fuse, -m-cresol is described in the literature. Yel trysts
which burns very rapidly and enables many shots (from et acet), mp 299°; insol in ether & pert eth;
to be fired simultaneously S1 SOI in hot ale, w & ethyl acet; easily sol in hot
The manuf of Bickford fuses began in the US benz. Was prepd by Steinkopf et al by heating with
in 1836, in France 1839 and in Germany 1844. The weak nitric acid the product obtained on diazotiza-
name of the current US firm is “The Ensign-B ick- tion of m-toluidine hydrochloride. Its expl props
ford Co” which is located at Simsbury, Corm. This were not investigated. Forms salts, such as those

——_ . —.—.—~ .-.

 B 113

of Amm and of Na yield was poor but better than that of Marquis.
R e/s: l)Beil 6,[973] 2) W.Steinkopf et al, JPrakt- Rinkes also proved the structure of the dinitro
Chem 110,355(1925)& CA 20,187(1926) -compd
Note: No higher nitro compds and no 1ater info on Refs: l)Beil 19,32 2)R.Marquis,AnnChimPhy s[3]
the above compds were found in CA through 1956 4,223 & 225(1905) 3)1. J. Rinkes,Rec 50,981-5
(1931) & CA 26,982(1932)
“Bicycle Pistol” (Radfahrer-Pistol, in Ger), This Trinitro-, CeH3N9 OS and Tetrarzitro-, C8H2N40, o
name is mentioned in SS 6,398(1911) & CA 6,547 Derivatives were not found in Beil or in CA thru
(1912) in connection with an expln in the Berlin 1956
post office, but no description of pistol is given
Big Bertha; Paris Gun and Other German Big Guns
Bicyclopentomethylene.2,4,6,8-tetramine;2,6-Di- of WWI and WWII. Many big guns were developed
nitro(DPT). See 3,7-D initro-l ,5-endomethylene-l, in Germany some of them with a max range of ca
3,5, 7-tetraza-2,4,6,8-cy clo~ctane under 1,5-Endo- 120km. Following is an incomplete list of such
methylene- 1,3,5,7-tetraza-2,4,6,8-cyclooctane guns:
a) Paris Gun(Parisgescb~tz) or Long Range Gun
BID. A cast double-base proplnt developed at ABL. (Ferngescb;tz) was a 21cm(ca 8“) weapon with the
Its compn & props are given in conf PropeIIant length of the tube 34m. Its max range was 120km.
Manual SPIA/M2(1959),Unit No 498 As the life of these guns was only 50-60 rounds,
they were rebored to 240mm and later to 260mm
BIE. Ditto, Unit No 499 (Ref 1). According to Ley(Ref 3), the guns 21cm
L/150 and 23.5cm L/132 were known as Paris
Bielefeld Explosive, patented in 1896 for use in Guns. The official Ger name for both of these guns
coal mining, consisted of Na nitrate 69, K nitrate was Kaiser Wilhelm Gescb~tz. The gun crews made
5, sulfur 10, coal tar 12 & K bichromate 4% no distinction between the two types and used the
Ref: Daniel(1902),70 nickname Die Pan’serin(La parisienne, in Fr).
These guns were sometimes erroneously called Big
Bielefeld’s Gelatinization Method, patented in Berthas b)24cm L/30 to L/40 Guns, such as
Germany in 1896-7, consisted of treating expls, Tlreodor, Tbeodor Bruno, Naval, Seacoast and
such as NG, nitrobenzeae, nitromolas ses, aromatic Krupp(Refs 3 & 6) c)24.4cm Howitzer, presumably
nitrocompds, etc per se or in the presence of dry- called Alpha(Ref 3) d)28cm L/40 to ~/50 Guns,
ing oils, resins, alcohol, etc with sulfur monochlor - such as Brrino, Tbeodor Bruno, L eopo14Anzio
ide(SzClz) at very low temps. The resulting jelly Annie), Railway and Naval(Refs 5 & 6) e)28cm
was mixed with oxidizers, such as nitrates, and L/12 & L/14 Coast Howitzers(Schwere K~sten-
with fuels, such as sawdust, flour, etc and then haubitze)(Refs 3 & 6) f)30.5cm L/50 Naval and
cartridged(compare with Parke’s Absorbents) Seacoast Guns(Ref 6) g)30. 5cm L/17 Howitzer,
nicknamed Kartatme in honor of the Ger 15th cen-
Bifuel Rocket Engine. Same as Bipropellant tury gun(Ref 3) h)30. 5cm L/12 Howitzer(Mortar)
Rocket Engine (Scbwere K~stenm~rser) and 30.5cm L/16 Howitzer,
called Beta 09 L/l 6 (Ref 3) i)31. Ocm GIStt Gun
Bifuryl and Derivatives on Railway Mount(Ref 6) j)35 or 35.5cm Howitzer
M-l(Ref 6) k)35.6cm L/52.5 Gun, built by the
a,a ‘- Bifuryl(2,2 ‘-Difuryl or-a,a ‘-Difuryl), C8H602;
Krupp Co for the Greek battleship Basileos
is described in Beil 19,[26] Gbeorgios but requisitioned by the Germans before
5,5 ‘-Dinitro-a, a’-bifuryl, it was deli’ sred{Ref 3) 1)38. Ocm Sieg/ried Rail-
H$—$H H;—~H , mw 224.13, N road Gun, And 38cm Naval Gun c/34(Ref 6k m)
02 N. C.0.C —C.0.C.N02 38. lcm L/45 Coast Defense Gun, nicknamed
12.50%. Yel-brn prisms with blue reflection(from Lange .Emil(Ref 3) n)40.6cm Adol/ Gun(Ref 6)
benz), mp 213-4°; insol in alkalies & dil acids. o)42. Ocm Howitzer, called Gamma M~setfRef 6)
Was first prepd by Marquis in 1905(Ref 2)by treat- p)42.Ocm L/14 Howitzer(Mortar), designated as
ing furan with fuming nitric acid(d 1.51) in presence KMK Ll14(Kurze Marine Kanone, L ~nge 14) and
of acetic anhydride. The yield was poor. Rinkes nicknamed Dicke Bertha(Fat Bertha, not referring
(Ref 3) prepd it on heating 2-bromo-5-nitrofwan to Frau Bertha von Krupp), Dickes L udefiFat
with the activated Cu powder of J. Piccard. The Wench) or Tante uus Es.sen(Aunt from E ssen), cal-
 B114

led in English Big Bertha@efs 3 & 6). This weapon Refs: l)Beil 3,93,(44) & [76] 2)E.C.Franklin,
fired a projectile weighing ca 1 tonto a distance “The Nitrogen System of Compounds”, Reinhold,NY
of ca 11 miles(Ref 5). These guns were construct- (1935),97-98 3)R.L.Sperry & E. O. Hook, USP2371111
ed during WW1 q)42.Ocm L/16 Howitzer, called (1945) & CA 39,3545(1945), BritP 579867(1946)&
KA!K Gamma or Eisenbabn 42(Railroad, model 1942) CA 41,1700(1947) (Prepn of biguanide and alkyl bi-
(Ref 3) r)53.34cm Gun, designated as Ger~t 36 guanides from the corresponding Cu biguanide sul-
(Ref 6) s)54.Ocm Heavy Howitzer, called Karl fates) 4)P.Oxley & W. F. Short,JCS ]951,1253 &
M~rser or Karl Ger~t(Ref 6). According to J arrett, 1255(Prepn of biguanide by heating an equimol
“Achtung Panzer” ,Great Oaks,RD l, Aberdeen,Md mixt of cyanoguanidine & ammonium sulfonate) P.
(1948),p 98, there were 54.Ocm and 61.Ocm Rochlin,D.B.Murphy & S. Helf,JACS 76,1453(1954)
weapons called Thor and Karl Mortars, but, ac- & CA 49,3951(1955) (Relative basicity of biguanidd
cording, to Ley(Ref 3), the Thor was likely to be a Biguanide Complex Compounds With Bivalent Metals
61.Ocm weapon t)61.Ocm Thor M~rser It was used were studied by P .R~y et al, JIndianChemSoc 16,
during WWII at the siege of Sevastopol(Ref 6,P Ger 617-20( 1939); 18,217-24( 1941); 18,609-22(194 1); 18,
263) u)61.5cm Karl M~rser(Ref 6). According to 289-306(1941); 18,609-22( 1941); 20, 19-21(1943) 20,
Ley(Ref 3), the Germans used at the siege of 291-7(1943); 2 1,163-6(1944); 25,563-70(1948): 26,
Sevastopol the following super-heavy weapons: 144-8(1949); 27,411-15( 1950); 27,651-4(1950>
61 .Ocm rifled mortar(short howitzer); 69.Ocm short, [see also CA’s: 34,4683(1940); 36,718(1942); 36,
rifled Naval gun, railroad mounted; and 71.5cm 2804-5(1942); 36,5440(1942); 37,6578(1943); 39>
rifled mortar(short howitzer) v)80. Ocm Gun, nick- 4559-60(1945); 43,7365(1949); 43,8941(1949); 45,
named Dora or Gustav Gescbiitz, was used during 6594(1951); 45,8390(1951)]
WWII at the siege of Sevastopol and for this reason Biguanide Complex Compounds With Trivalent
was known as Sevastopol Gun. Porter (Ref 4) calls Metals were studied by P .R~y et al, JIndianChem
it Big Bertha o~ WW1l. A brief description of the SOC ~4,670-84(1937); 15,347-58(1938); 15,633-8
Sevastopol Gun is given in Ref 4 and in Ref 6,pp (1938); 16,621-33(1939); 23,73 -84(1946); 25,589-90
Ger 176 & 259. The above gun was sometimes re- (1948); 26,137-43(1949)
ferred to as the 82.Ocm gun [see also CA’s: 32,3721(1938); 33,493-4(1939); 33,
Re/s: l)H.W.MiIler,ArmyOrdn 4,98-100,122 & 167 53 14(1939); 34,4683-4(1940); 41,44-6(1947); 43,
-176( 1923)( The German Long-Range Gun) 2)H.W. 7365(1949); 43,8941(1949)]
Miller, ArmyOrdn 16, 10-17 (1933 )( Behind the Paris Biguanide Complex Compounds With Tervalent
Gun) 3)~.Ley, Coast Artillery Journal, Jan-Feb Metals were studied by P .R i5y et al, JIndianChem
1943,pp 14-15 4)F.B.Porter,ArmyOrdn 31,254-6 SOC 19,1-8(1942) & CA 36,5721-2(1942)
(1946) (Big Bertha of W~’11) 5)G. B.J arrett,Ordn 35, Biguanide Explosive Salts include Biguanide Chl~
397-8(1951) (That Fabulous 1918 Paris Gun Again) rate. See under Biguanide P erchlorate and Chlo-
6)PATR 251O(PB NO 161,270 )(1958),PP Ger 257-9 rate
Note: According to Ref s,p 398, there was a book Biguanide Nitrate, C2H7N5 .HNC)3 ; prism s(from w),
by H. W. Miller, “The Paris Gun”, published in 1930 mp 192°. Can be prepd by fusing cyanoguanidine
with Amm nitrate. Manuelli & Bernardini(Ref 2)
Big Inch Blasting Cap, Western. See under Blasting proposed using biguanide nitrate as an ingredient
Caps of expl compns
Refs: l)Beil 3,(44) & [76] 2)C.Manuelli & L.
Biguanide and Derivatives Bernardini,BritP 138371(1917) & CA 14,2086(1920)
Biguanide or Guanylguanidine (called Guanidincarbo- 3)T.L.Davis,JACS 43,2235(1921) 4)J.S,Blair &
ns~ureamidin in Ger),H#.C(:NH).NH. C(:NH).NH2, J. M. Braham,JACS 44,2349-50(1922)
mw 101.12, N 69.27, OB to C02 -118.7%. Prisms Biguanide Perchlorate and Chlorate can be prepd
(from abs alc in C02atm), mp 130°; very sol in w by heating cyanoguanidine with Amm perchlorate
and in ale; insol in eth, benz or chlf. Can be prepd or chlorate resp. They were proposed by Manuelli
from cyanoguanidine( dicyandiamide), & Bernardini(Ref 2) for use in expls
H2N.C(:NH).NH.CN, by one of the methods de- R efs: l)Beil- not found 2)C.Manuelli & L. Ber-
scribed in the literature(Refs 1 & 2) nardini,BritP 138371(1917) & CA !4,2086(1920)
Many of its salts(some of them explosive) can Biguanide Picrate, C2H7N5.C6H~N306; yel ndls
easily be prepd by heating(or fusing) cyanoguani- (from w), mp 232°; sl sol in w and in ale. Can be
dine(dicyandiamide) with the corresponding Amm prepd either by the action of an aq soln of PA on
saIt in the propn of 2 to 1 resp biguanide(Ref 1) or from biguanide sulfonate and

—— , —. --___ .—”___ —— . . . .—. .—-—..-.—

 B115

Amm or Li picrate solns(Ref 2). Its expl props 1,5,4’ (or 1,5,5’)* Trinitrobiimidazole [called 1.5.4’-
were not investigated (bzw 1.-5.-5’)- Tn”nitro-diimidazolyl-(2. 2’) in Ger],
Refs: l)BeiI 6,279 2)P.Oxley & W. F. Short,JCS C6H3N706, mw 269.14, N 36.43%. Lt brn lflts
1951,1255 with 1.5H20; expl on rapid heating; very cliff SOI
Biguanide, Analytical Procedures are described in w, alc or eth. Was obtained by Lehmstedt as
in the following Refs: one of the products of nitration of biimidazole.
I)J.S.Blair & J. M. Braham,JACS ~,2347(1922) Its salts are dark red in color
(Method of detn of biguanide based on the insoly Refs: l)Beil 26,[215] 2)K. Lehmstedt,Ann 456,
of Ni biguanide in alkaline soln) 2)C. D. Garby, 270(1927) & CA 21 ,3364(1927)
IEC 18,819(1926) Detn of biguanide as its Ni 1,5,1’,5’=Tetranitro.2,2’. biimidazole [called
salt, Ni(C2H6 N5 )2 1.5, 1‘,5’-Tetranitro-diimidazolyl-(2. 2’) in Ger],
H$— N< — $H , mw 314,14,
N
Biguanidine and Derivatives
‘c. eN
02 N. C-(02N)NZ 8N(N02 )-C .N02
Biguanidine(ffydraz obisformamidine or Hydrazoa’i- 35.67%. Yel prisms with 2H20, mp- dec ca 276°
carbonamidine), H2N.C(:NH).NH.NH .C(:NH).NH2, and is very explosive. Sol in w, ale, ether or ethyl
mw 116.13, N 72.36%. Its dinitrate, acetate. Can be prepd by nitration of biimidazole
C2HsN~ .2 HN03.H20, trysts, mp 132 °(with evoln with coned nitric and sulfuric acid as described
of gas); defl at 181°; was prepd by Thiele, Many in Refs 1 & 2
derivs of biguanidine, including the dinitro comp, It forms salts, most of which are explo~ve.
are known but no description of biguanidine itself Eg: Disodium salt, Na2C~Ns 08 .2H20, orange-red -
cou!d be found trysts, expI on heating; Dipotassium salt,
Re/s: l)Bei13,120 2)J.Thiele,Ann 270,42(1892) K2C6NeOe .2H20, red-brn ndls, expI on heating;
& 273,140(1893) Disilver salt, Ag2 C6Ns08 .2H20, gelatinous brn
l,~Dinitrobiguan idine, ppt, expI on heating
02 N. HN.C(:NH).NH.NH. C(:NH).NH.N02, mw Refs: l)Beil 26,[215] 2)K.Lehmstedt,Ann 456,
206.14, N 54.36%. Col trysts, mp 193-5° with 272-3(1927) & CA 2 1,3364(1927)
vigorous decompn. Henry et al(Ref 2) prepd it in
20-25% yield by the reaction of nitroaminoguanidine Biimidazoline and Derivatives
and l-methyI-l-nitroso-3 -nitroguanidine or in 55% 2, 2’-Bi-(2-imidazoline) or Bis-(A2-2-imidazolinyl)
yield by the hydrogen sulfide reduction of azobis- { called Di-[A2-imidazoliny l-(2)] in Ger],
nitroform amidine H2C—NN >N—CH2
Refs: l)Beil- not found 2)R.A.Henry,S.Skolnik & I C.c I mw 138.17, N 40.55%.
G. B. L. Smith,JACS 75,955 & 958(1953); CA 48, H2C-HN’ \NH-CH2’
2050(1954) Prepn and props are described in Refs. Forms
salts, such as picrate, yel powder melting with de-
Biimidazole and Derivatives compn at 272-3°
Biimidazole,[called Diimidazyl-(2. 2’) in Ger], Re/s: l)Beil 26,353 2)G.Forssel, Ber 24,1846
HC-N N-CH, mw 134.14, N 41.77%. Ndls which (1891) & 2!3,2132(1892) 3)H.M.Woodburn & R.C.
II ~-< (1 O’Gee,JOC 1~, 1236 & 1241-2(1952)& CA 47,
HC-fiH Hfi-CH 8066(1953)
sublime without reeking. Was prepd in 1859 by H. 2. 2’-Bi-( l-nitroso-2-imidazoiine){ called Bis-[ 1.ni.
Debys under the name of Glycosin(Ref 1). Several troso-A2-imidazoliny l-(2)] in Ger],
metallic and org salts are known(Refs 1,2 & 3) H2C— N> ~N—CH2
Refs: l)Beil 26,358,(111) & [214] 3)K.Lehmsted6 I ,C.c= I , mw 196.17, N
Ann 456,253(1927) & CA 2 1,3364(1927) 3)K. H2C-(ON)N’ \N(NO)-~H2
Lehmstedt,Ann 507,213-25(1933) & CA 28,767(1934) 42.84%; greenish ndls(from ale), mp 173° (dec).
1,4’ (or1,5’)sDinitrobiimidazole [called 1.4’(bzw Was prepd by Forssel by treating 2,2‘-bi-(2-imid-
1. 5’)-Dinitro-diirnidazoly l-(2.2’) in Ger], C H N O oline) with K nitrite and coned AcOH
mw 224.14, N 37.50%. Yel lflts with lHzO~ ~p ~83t Refs: l)Beif 26,363 2)G.Forssel,Ber 25,2133
(dec); weak expl. Was obtained by Lehmstedt as a (1892)
by-product during prepn of tetranitrobiimidazole Note: No mono- or di-nitro compds were found in
(qv). Its salts are reddish in color Beil or in CA through 1956
Refs: l)Beil 26, [215] 2)K.Lehmstedt, Ann 456,
271(1927) & CA 21,3364(1927) Bikarbit. Same as Bicarbite
 B 116

BIL and BIM are castdouble-basep ropl~tsdevel- some attempts were made to use them for shell
oped at ABL. Their compn and props are given in loading. Many Dynamites are, however, suitable
conf propellant klanual SPIA/M2 ( 1959), Unit NOS as military demolition expls. Dynamites contg col-
500 & 501 Iodion cotton are called Gelati?~ Dynamites and
the strongest of such mixts is Blasting Gelatin.
BINARY, TERNARY AND QUATERNARY Stettbacher(Ref 12b) proposed in 1929 an expl
MIXTURES. These mixts may consist of two, three mixt known as Pentrinit which may be considered
or four components being either exclusively expls as a non-freezing, very powerful d ynamite and
or one or more expls with non-expls, such as oxi- which is suitable for military purposes. It con-
dizers(AN, K chlorate, K perchlorate, 13a nitrate, sisted of NG and at least 207. of PETN. By incor-
peroxides, etc), pulverized fuels(such as C, Al, porating 4 to 6% of collodion cotton in such mixts,
h~g, Zr, etc) or fuels which may act as binders, de- the so-called Gelatinpentrinits were obtained
sensitizers or waterproofing agent s(such as wax, One of the first known castable military expl
paraffin, shellac, resins, plastics, etc) mixt is probably the French M; lange DN 60/40,
These mixts can be either eutectics(partly or also called DD 60/40, developed with the inten-
completely) or non-eutectics and the purposes of tion of overcoming the difficulty of cast-loading
the mixts can be as follows: straight M;linite (PA). In the DD 60/40 expl:
a) To facilitate cast-loading into shells, bombs, P A60 & DNPhenol 40%, the 2nd component lowers
warheads of rockets, etc, of high mp expls, such the mp of PA from ca 122° to ca 85°, while at the
as PA, PETN or RDX same time it reduces the expl characteristics of
b) To improve the expl characteristics of some PA(Ref 15). Many other binary, ternary, etc mixts
HE’s, such as mixing them with oxidizers or were developed in France in addn to llD 60/40 and
pulverized metals most of them are listed in this section
c) To stretch an insufficient suppIy of some expls Many of the mixts developed during TTI in Ger-
(such as TNT), which might accur during a war many, GtBritain, Russia and the US were intended
d) To render some expls(such as PETN, RDX or to stretch the available supply of TNT and of
Tetryl) less sensitive to mech action, which can other HE’s. The most important of such compo-
be accomplished by mixing them with wax, paraffin, sitions were mixts of AN and TNT, called
et c Amatols. As the shortage of TNT and of other HE’s
Historical. If one does not take into consideration was even more acute in Germany during WWH than
BkPdr, which is a ternary mixt of an oxidizer(K during WWI, many substitute expls(called Ersatz-
nitrate) and fuels(C & S), and the unsuccessful sprengstoffe) were developed. Some of these expls
attempts of BerthoHet, Augendre and Blake(see consisted of NaCl and TNT. To a lesser extent
Ref 4b,p 309) to improve BkPdr by replacing K this shortage of TNT was felt in Russia(Ref 9a &
nitrate with K chlorate, the first successful mixts 12c). The US arid GtBritain were, however, fortu-
suitable for blasting and for some military purpos- nate to obtain during WWI1 an abundant supply of
es were expls proposed beginning in 1871 by H. TNT due to the Amer development of synthetic
Sprengel. These expls were liquid and solid. The toluene from petroleum. This abundance of TNT
liq expls consisted of a Iiq oxidizer(such as strong rendered practical the development of new binary,
nitric acid or nitrogen peroxide) and a li q or solid ternary, etc mixts in which TNT was utilized as a
fuel (such as MNB, MNN, PA, petroleum, etc). The carrier for more powerful expls(such as PA, Tetryl,
solid Sprengel expls, now known as Cheddites, PETN, RDX, EDNA, etc), which alone were not
consisted of an oxidizer(chlorate or perchlorate) suitable for cast-loading because of high mp’s.
and a fuel(PA, MNB, MNN, etc) (Ref 5a,p 354). The resulting mixts are known as Picratols, Tetra-
E. Street rendered Cheddites less sensitive to tols, P entolites, Cyclotols, Ednatols, etc. Another
mech action by incorporating some castor oil(or development in the direction of binary and ternary
other desensitizer). These mixts were sometimes expl mixts was the incorporation of Al powder.
called Street Explosives or Streetites(Ref 4a,p These mixts, known as Aluminized Explosives,
310). Later composite expls, Anilithe, Hellbo/ite, are described in Vol l,p A146-L and have pro-
Oxonite, Oxyliquite, Panclastite, Prornetb6e, nounced increased blast effects(Ref 15)
Rack-a-Rock, etc, were only modifications of Binary mixts and their eutectics were examined
Street expls. However, none of these expls was by many investigators, such as Giua(Ref 1),
suitable for loading shells. The same may be said Wogrinz & V5ri(Ref lc), Taylor & Rinkenbach(Refs
about Dynamites, invented by A.Nobel, although 2,3 & 3a), Urbaiiski(Ref 4a), Campbell et al(Refs
*

..— . -— ________________________ .,.—_ —

 B 117

10,ll& 12), Ficheroulle(Ref 12a), Desseigne(Ref Scbneidetite or Explosi/ Sc(or S) (AN 87-8 & DNN
13) & Yamasue et al(Ref 17) 13-12%), Xylite P (PA 50, TNT 40 & TN-m-xylene
Ternary mixts were investigated by Tomlinson 10%) [Refs 4b, 5a and the books of PascaI(1930),
(Ref 6), Phillips(Ref 7), Aaronson(Ref 8), Eriksen Venin, Burlot & L6corchrS (1932) and Pepin-LehalIeur
(Ref 9), Campbell et al(Refs 10 & 11) and M6dard (1935)1
(Ref 13c) Germany: Amatol 39 (DNB 50, AN 35 & RDX 15%);
Some quatenary mixts were used in Germany
Amatol 40( DNAns 50, AN 35 & RDX 15%); Amatol
during WWI1, eg: Arnmonit .S-6 which consisted
41 (AN 52, tech Ca nitrate 6, EDADN 30, RDX 10
of TNT 40, HNDPhA 30, GuN 20 & Al Powder
& montan wax 2%); Ammonal I (AN 54, TNT 30 &
10%; and KMA BIock which contained TNT 40,
Al 16%); Ammonal II (AN 72, TNT 12 & Al 16%)
HNDPhA 30, DNN 20 & Al powder 10%(Ref 17,
(Ref 18,p Ger 4); Ammonit 43C (AN 45, tech Ca
p Ger 44)
nitrate 10, GuN 15 & TNT 30%; emulsifier, ‘Vult-
Thomas(Ref 16) described a method of analysis
amol” , added 0.5%); Ammonit HI (AN 50, tech Ca
of some binary expis using a solvent for sepa-
nitrate 15, PETN 10 & RDX 25%) (Ref 18,p Ger 6);
rating the components
Ammonit H8(AN 50, K nitrate 25, RDX 15 & PETN
The following is a selected list of binary, ter-
10%); NaCl Explosive (TNT 40-50 & NaCl 40-50%)
nary, and quaternary expls, foreign and US:
(Ref 18, p 44); Fillers 32 to 38( PETN-WaX in
Belgium A1.silite(see Vol l,p A141-R); Baelenites various propns); Filler 45 (PETN 50 & TNT 50%
(see Vol 2); Ca.steau(AN 90 & nitrodextrin 10% with with 30Z wax added); Filler >2 (DNB 50, AN 35 &
or w/o 5% resin added); Centrality TA(AN 79.5, RDX 15%); Filler 86 (EDADN 46, RDX 18 & wax
TNT 14.5, RDX 2.0, DNT 1.0 & Al powder 3.0%); 36%); Filler 92-H1O (RDX 90 & wax 10%); Filler
Coopalite(AN 79, TNT 13, NG 4 & woodflour 4%); 105 or Trialen 105 (RDX 15, TNT 70 & Al powder
Dynamite I{f (AN 62.0, NG 26.0, DNT 9.5, cellu- 15%); Filler 106 or Trialen 106 (RDX 25, TNT 50
lose 1.3 & NC 1.2%~ Favier Explosives (mixts of & Al 25%); Filler 107 or Trialen 107 (RDX 20, TNT
AN with DNN, TNT & other ingredients); Maca- 50 & Al powder 30%); Filler 108 or Tritolital(RDX
rite (Pb nitrate 71.9 & TNT 28.lyo); M6gadyne(mixt 20, TNT 60 & Al 20%); Filler 109 or Trialen 109
of Amm perchlorate, Al powder & paraffin wax); (RDX 70, Al 25& wax 5%) (Ref 18,pp Ger 46-8);
Permite(AN 78, TNT 8 & Ca silicide 14%); V;l- Hexamin Explosives (such as HNDPhA 27.9, TNT
terine(AN 93 & Amm trinitrocre sylate 7%); WaZ- 55.7 & Al 16.4%) (Ref 18,p Ger 88); Monakit I(An
lonite(AN 90 & Nitrotar 10%); yonckites(mixt of 81, K or Na nitrate 5, TNX 13 & flour l%)(Ref 18,
Amm perchlorate with MNN, TNN, TNT and other p Ger 114); Nitrolit (TNAns 60 & AN 40%)(Ref 18,
ingredients) [Dr L. De ffet, Bruxelles, private com- p Ger 122); Pentritols (PETN/TNT in various
munication 1954) and other sources] propns) (Ref 18,p Ger 128); PH-Salt Explosives
(see Ref 18,p Ger 132), R-Salt Explosives(see
France: Ammonal(AN 82, TN’T 6, DNT 5, Al 5 &
Ref 18,p Ger 70); Trialen (see Fillers 105, 106,
woodrneal 2%)(See also Vol l,p A290 Table);
107 & 109); Tritolital(see Filler 108); Tritrinaz
Cr;sylite 60/40 (Trinitro-m-cresol 60 & PA 40%); (TNT 2 parts & TNN 1 or 2 parts)(Ref 18,P Ger
Explosifs nitrat;s G Explosifs nitrat~s ~ l*alumin-
209); Unterwassersprengsto//e (Ref 18,P Ger 212
ium (See N2TN, NDNT, NT, NTN, NX and Refs -13)
5a & 13a); ExpIosi[ S(or SC)- same as Schneiderite;
Note: Many other composite Ger expls are listed in
MDN or MFDN(PA 80 & DNN 20%); MDPC{PA 55, Ref 18
DNPh 35 & TNCrs 10%); M~linite 0- see hiO;
M61inite P- see MP; MMn (PA 70 & MMN 30%); MO Italy: Albite(see Vol l,p A120-L); ANS(see’ Vol 1,
(M61inite O) (PA with some TNCr); Mp (M61inite p) p A457-R); Cheddites (such as K chlorate 80, MNN
(PA 88& paraffin 12%); MT’7’C(PA 55, TNT 35 & 12 & castor oil 8%; Amm chlorate 82, DNT 13 &
TNCrs 10); MTX(PA 55, TNT 35 & TNX 10% or castor oil 5%; Na chlorate 75.0, MNT 23.2 & collod
PA 30, TNT 25 & TNX 45%); N2TN(AN 50, Na cotton 1.8%); Cremo,nite (AN 48.8 & Amm picrate
nitrate 30 & TNN 20%); IVDNT (AN 85, DNN 10 & 5 1.2%); Cyclonite-AN-Wax MiIitary Explosive(RDX
TNT 5%); NT(AN 70 & TNT 30%); NTN(AN 80 & 22.0, AN 73.4 & wax 4.6%); Cyclonite-Wax Military
TNN 20%); NX (AN 77 & TN-m-xylene 23%) Pan- Explosive(RDX 95 & wax, dyed red 5%); Dinamiti
clastites of Turpin(mixts of liq fuels such as MNB (Dynamites; many compns are known); Dinamon(AN
gasoline, CS2 with liq nitrogen peroxide) (Compare 69, K chlorate 8, TNT 20 & Al 3%); Dinitronapb-
with Anilithe, described in Vol l,p A443-R); tbalene-Containing Explosives (MST or Nougat,
 I

B 118

Schneiderite and Siperite); Dinitrotoluen e-Contain- Explosive); Haensosan-bakuy aku(see under Type
ing Explosive s (such as DNT 19, collod cotton 1, 88 Explosives); Haishokuyaku No 1 (Amm perchlo-
Na chlorate 59 & PETN 21% or DNT 17, TNT 3.5, rate 76.9, RDX 17.0, paraffin 4.8 & Si carbide 1.3%);
PETN 18, collod cotton 0.5, Amm perchlorate 36, Haishokuyaku No 2 (Amm perchlorate 48, GUN 20,
& Na nitrate 25%); Echo or E.scbo(AN 62, Al 25, RDX 25, paraffin 5 & graphite 2%); Hexamit[see
fat 7.5 & N 5.5%); Esplosivo da guerra, listed in A(ko), also called Otsu-B or Type A Explosive];
CA 451770(1951) (TNT 30-90, PETN 65-5 and Al Karritto (see under Type 88 Explosives); Ko (see
powder 5-30%; part of the TNT may be substituted under Type 88); Kosbitsu or .$houyaku-koshitsu
by DNN); Esplosivo da guerra, listed in CA 44, (RDX 80 or 85 & oil 20 or 15%); Mk 2 (see Nigo-
6130(1950) (RDX 75-90 & Al powder 25-10%); Es- tanyaku Mk 2); Nigotanyaku Mk 2( TNT 40-70 &
plosivo da rnina, listed in CA 45,1709( 1950)(RDX RDX 60-30%); Orzayaku (PA 50 or 80 & DNN 50 or
or PETN 75 & nitro-iso-butylgly cerintriacetate 25%); 20%); Oshitsuyaku (RDX 80 & vegetable oil 20%);
Esplosivo da rnina, listed in CA 45,3160(1951)[TNT Osbiyaku (PA 90 & wax 10%); Otsu-B [ see A(ko)];
(of which up to 50% may be substituted by DNN) Pentoriru (PETN 50 & TNT 50%); Seigata(see
30-9, RDX 65-5 & A] powder 5-30%]; Esplosivo Type 97 Explosive); Sboanbakuyaku (AN 79, DNN
plastico, listed in CA 43,7688( 1949)(RDX 85-89, 10, NaCl 10 & sawdust l%); Shoayaku (mixts of AN
petrolatum 10-12, thiocol 0.5-2 & glycerophthalic with DNN, TNT, GUN, NaCl, woodmeal, etc);
resin 0.5-2%); Filler FNP (AN 73, PETN 20 & wax Sboberryaku of Nanman Arsenal(see Anbenyaku in
5%); Filler /07 .500-kg ‘Time Bomb(PETN 65 & penta- Vol l,p A401-R); .shoberzyaku of Tama Factory
erythritol-tetraacetate 35%); FNP ( see Filler FNP ); (mixt of DNB, Tetryl & An); Sboeiyaku Explosives
GDI, GDli, GD2, GDIM, GEO & GEOM are gelatin- (PETN 91.5 & wax 8.5%; PETN 58 & RDX 42%)
ized mining expls contg NG; Hidrolita (mixt of RDX (see also Pentoriru); .$horzayaku or Shorz-5-yaku
or PETN with AN, paraffin & 5-7% water); lm- (AN 90 & DNN 10z); Sbotoyaku (AN 50 & TNT 50%);
perialite(AN 85-90 & Al scales 15-10%); MABT Tanayaku Explosives (RDX 92 or 95 & wax 8 or 5%;
(mixt of PA, TNT & DNPh), MAT(PA 60& TNT RDX 83 & PETN 17%) (see also Angayaku, Koshit-
40%); MB T (PA 60 & DNPh 40%); MNDT(see under SU, Nigotanyaku and Type 94 Explosive); TanZyaku
Siperite); MST (see Nougat); Nitramite or Avigliatra (RDX 55 or 60, TNT 38 or 30 & Tetryl 7 or 10%);
3(see Vol l,p A516-R); Nitrona/tits (RDX 75-80 & Torpex-Typ e Explosive (AN 43.2, GuN 28.8, RDX
MNN 25-20%); Nougat or MST (AN 50, TNT 43 & 8.0 & Al 20.0%); Type 1 Explosive (Amm picrate
DNN 7%); PAM & PANA (expl mixts based on PETN); 81, Al 16, heavy oil 1 & woodpulp 2%); Type 1,
PETN Explosives(mixts of PETN with wax, TNT, Mk 5, P5 (Amm picrate 86, ferrosilicon 11, heavy
DNT, NG, AN, PETA, etc); Piombite(Pb nitrate oil 1 & woodpulp 2Y0); Type 2( B4)(TNAns 60 or 70
76, TNN 16, ca silicide 5 & vaseline 3%); PNP(AN & Al powder 40 or 30%); Type 88( Navy) or Karritto
75, PETN 20 & wax 5%); Sabulites (mixts of AN (Army) (AN 66, Si carbide 16, woodpulp 16 & petro-
with Ca silicide and TNT or TNN); ScZmeiderite(AN leum 6%); Type 88(Ko) or Haensosan-bakuyaku
87.5 & DNN 12.5%); .$iperite or Syperite (AN 72.8, (Amm perchlorate 75, ferrosilicon 16, woodpulp 6
DNN 10.5 & TNT 16.7%); Sol/ite (AN 83-8 & S 17 & heavy oil 3%); Type 92 (Navy )(means straight
-12%); Stabilites(mixts of NG, TNAns & NG); TNT as well as the mixt of TNT 66 & Al powder
Toluolammonal (AN 47, TNT 30, Al 20 & carbon 3%); 34%); Type 94M (Navy) (TNAns 60 & RDX 40%);
Tritolita or “Tritolol (mixts of TNT with RDX in Type 97H (Navy) (TNT 60 & HNDPhA 40%); Type
various propns); “Tritolital (TNT 60, RDX 20 & Al 98H2 Korzgo (Navy & Army) (TNAns 70 & HNDPhA
20%); Tritolol (see Tritolita); Umhrites(NG 45.1 or 30%); Type A see A(ko), VOI l,p Al19-L)(Ref 8a
48,4, AN 41.4 or 37.3 & ferrosilicon 13.5 or 14.3%); and other sources)
Vibrite (AN 78, TNN 8 & Ca silicide 14%); Victo- Russia: Almatrites(see Vol l,p A140-L); Arnatols(
n“te [PA 53.7, K(Na or Ba) nitrate 4.9, K chlorate (such as AN 80 & TNT 20% and AN 86.8 & TNT
39.0 & carbon 2.4%) (Refs 9b, 14a, 15a and other 13.2%); Ammokcil or Ammoksil (see Vol l,p A286
sources) -R); Ammonals (such as AN 82, TNT 12 & Al pow-
Japan: A(ko)(see Vol l,p Al 19-L); Ammona&(same der 6%); Ammonits (such as AN 77.6, TNT 18.4 &
as Ammonal); Ammonyaku (see VOI l,p A383-L); woodmeal 4%); Arnmorzit-Goudronit (see Vol l,p
Anbenyaku or Sh6benyaku (see VOI l,p A401-R); A31o-L); Ammonpek (see Vol l,p A382-L); Am-
Arrgayaku(see Vol l,p A402-R); B4(same as Type montol or Russkaya Sines’ (see Vol l,p A383-L);
2 Explosive); Chanayaku (TNT 50 & RDX 50%); “~ Baronal- Type Explosive (Ba nitrate 38.9, Al pow-
(TNAns 60 & AN 40%); Erzrrayaku (K chlorate 80, der 46.1, TNT 14.7 & sulfur 0.3%); Bellites(see
MNT 15 & castor oil 5%); H2-Kongo(see Type 98H2 Vol 2); Dinamony (such as paraffined AN 89-90&

_ .—.———.
—.-.—..——
 B 119

fuels, such as peat, 11-IOZ); Dirzitrobenzene-Con- and Ref 4b,p 316)

taining Explosz’ve.s (such as BeHites and K-1 Splav Switzerland: Alder/it (see Vol l,p A123-R); Ammon-
-see under Benzene, Dinitro); Dinitronaphthalene pentrinit(see Vol l,p 382-L); Gamsit or Gelatine
-Containing Explosives (such as TNT 92 & DNN -Gamsit(NG 21, NGc 5, collod cotton 1.6, woodmeal
8%; AN 87.5 & DNN 12.5%, Frantsuzskaya Smes’, 0.4, liq DNT 12 & AN 60%); GeLxtine-Alder/it(NG
K-2 Splav, Rus skii Splav and Schneiderite-Type with or w/o NGc 22, collod cotton 1.5, Iiq DNT
Explosives); Fielder Explosives (mixts of 80/20 with TNT 13 & AN 63.5%); Gelatirze-Cheddit (Na
-MNB/tutpentine with K chlorate & K permanganate); chlorate 79, coated with a.liq mixt of castor oil 5,
Frarztsuzsk,aya Sines’ (PA 80 & DNN 20%); DNT 2 & TNT 14 preheated to 40° ); Gelatine-Gam-
Gbeksogen Explosives (such as RDX 71.9, TNT sit) (See Gamsit); Gelatine-Pentn”nit (mixt of PETN,
16.4 & Tetryl 11.7%; RDX 75.1, Al 20.8 & binder NG & collod cotton, such as PETN 50, NG 46 &
4.1% and RDX 53 & TNT 47%); K-1 Splav(see under collod cotton 4%); Gelatine-”Telsit (NG with or w/o
Benzene, Dini.tro); K-2 Splav (TNT 80 & DNN 20%k NGc 22, collod cotton 1.5, DNT 21 & AN 55.5%);
L-Splav (TNT 95 & TNX 5%); Melinit Explosives Hexonit(such as RDX 20-50 & NG 80-50% or RDX
(such as Russkii Splav); Russkii Splav (PA 51.5 & 50, NG 46 & collod cotton 4%); Pentastit 93/7
DNN 48.5%); Schneiderite-Type Explosives (such (PETN 93, phlegmatized with 7$%pentaerythritol-
as AN 87.5 & DNN 12.5; AN 88 & TNN 12% and tetrastearate, with or w/o 20% AI added); P entastit
AN 82 & TNN 18%); Tetryl Explosives (such as 96.5/3.5 (PETN 96.5 & PETS 3.5% with or w/o
Tetryl 57 & TNT 43%); Trinitronapbthalene-Con- 3.5% Al added); Pentrinit (mixt of PETN with not
taining Explosives (such as Schneiderite-Type less than 20% NG); Pentro or Pentryl(mixts of
Explosives); Trinitrotoluene Explosives (such as PETN & TNT with or w/o Al powder); Plastit ( a
TNT 50-80 & RDX 50-20% and RDX 71.9, TNT plastic military expl based on PETN and manufd
16.4 & Tetryl 11.7%), (Refs 9a, 12c & 13b); Zhirov by Schweiz-Sprengstoff-Fabrik AG; its compn has
Explosives [see N. F. Zhirov,RusP’s 4283 & 4(1927); not been revealed); Simplonit (Gamist with 10-15%
CA 22,4821(1928)] AI added); Telsit (see Gelatine-Telsit); Telsit-
Sweden: Ammongelatine (see Vol l,p A295-R of Gamsit (same compn as Gamsit)[Dr A. Stettbacher,
this Encyclopedia); Ammoniakkrut (see Vol l,p Z~ich, private communication 1954) and other
A307-R); Ammonium Nitrate Dynamites or Extra sources]
Dynamites are probably similar to those described US and Great Britain: Alumatol (see Vol l,p A141
in Vol l,p A355; Black Powder (KN03 74-78, char- -R); Aluminized Explosives (see Vol l,p A146-L~
coal 12-15 & S 10-12%) (Ref 19,p 190); Blastines Amatol (see Vol l,p Al58-L); Ammonal (see Vol 1,
(see this volume); Bo/ors Plastic Explosive (see p A287-L); Baratol (see Vol 2); Baronal (see Vol 2);
this volume); Bonites (see this volume); Dynamites Boronite (see Vol 2); Compositions A,B & C (see
(many compns are manufd in Sweden by AB Bofors Vol 2); Cyclotols (see Vol 2); DBX (TNT 40, RDX
Nobelkrut, Nitroglycerin AB, AB Norma Projektil- 21, AN 21 & Al 18%); Ednatols (EDNA 50-60 & TNT
fabrik, AB Nora T~ndr~fsfabrik, AB Svenska Krut- 50-40,%); HBX (TNT 38, RDX 40, Al 17 & wax 5%);
faktorierna and probably by other plants); Gelatin Minex(TNT 40, RDX 5-15, Al 20 & Amm carbonate
Dyrzamites (see under Dynamites); HexotoIs, 35-15%); MinoLs(TNT 40 or 43, AN 40 or 37 & Al
(military expls RDX/TNT-60/40 or 50/50 manufd 20%); Octol (HMX 77 & TNT 23%)(Re f 20); Pento-
by AB Bofors Nobelkrut(Ref 19,p 201); Hexotonazs lites (PETN 10-75 & TNT 90-25%); PentonaZ(PETN
(military expls RDX/TNT/Al/wax-40/44/ 15/1 or 40, TNT 40 & Al 20%); PEP-3 (PETN 86 & Oil 14%);
40/44/1 5/5 manufd by A13 Bofors Nobelkrut; another Picratol (PA 52 & TNT 48%); PIPE (PETN 81 & oil
compn is RDX/TNT/Al/-3 0/50/20 with 1% wax and 19%); PTX-1 (TNT 14, RDX 21 & Tetryl 65); FTX
1.5% carbon black added)(Ref 19,P 203); Na~ckbol/’s -2 (TNT 28.8, RDX 43.2 & PETN 28%); PTX-3 (TNT
Explosive(Compn patented before WWI cent NH4C104 27, TetryI 18 & EDNA 55%); PTX-4 (TNT 31.5,
43, NH4N03 26 and 31% of soln prepd by dissolv- PETN 13.5 & EDNA 55%); RIPE (RDX 85 & oil
ing 4ps of collodion cotton in 96PS of liq TNT 15%); Sbezlite (PA 50 & DNPh 50%); .$odat?l (Na
(Ref la, pp 247 & 681); Novit (Underwater expl nitrate 50 & TNT 50%); Tetratols (Tetryl 40-80 &
of WWI contained (TNT 50 & HNDPhA 50% and of TNT 60-20%); Torpex(TNT 37 or 40.2, RDX 45 or
WWII: TNT 55.7, HNDPhA 27.9 & A1 16.4% )(Ref 41.5 & Al 18%); Tridite(PA 80 & DNPh 20%); Tti-
4b,p 294; Ref 5c,pp 38 & 41; Ref 9b,p 107); Territ monite (PA 90 & MNN 10%); Tritonal 80/20 (TNT
(Blasting plastic expl patented before WWI by AB 80 & Al 20%); Tritonal D-2 (80/20 Tritonal 95 &D2
Nitroglycerin: NH4C104 43.0, DNT & TNT 27.8, -wax 5%); uWE (same as Tritonal 80/20)
NsN03 28. O& collodion cotton 1.2%)(Ref 3b,p 135 Re/s: l)M.Giua,Gazz 45 i, 352-8, 557-66(1915) &
 I

B 120

CA 10,598,1775 (1916 )( Binary mixts of nitro derivs Schneiderite. For this reason the above mixts are
of toluene and benzene and their eutectics) not recommended for filling projs) 12b)Stettbacher
la)Colver( 1918),247 & 681 lb)Barnett(1919), 112 (1948 ),83-5 12c)Blinov 1(1948),17-20 13)G.
lc)A.Wogrinz & P V6ri,SS 14,249-51 & 267-70( 1919) Desseigne,MP 30, 127-37 (1948 )( Study of binary
& CA 14,3530( 1920) (Equilibrium diagrams of binary mixts of PETN with m-DNB, DNAns & DNPh)
mixts of PA, TNT, DNT & MNN) 2)C. A. Taylor & 13a)Blinov 2(1949),64-5 13b)L.M6dard,MP 32,
W. H. Rinkenbach, JIEC 15,73-7(1923) (Estimation of 213-16 & 223(1950) [Description of Explosifs fxi
the proportions of TNT & Tetryl from freezing nitrat;s and Explosifs nitrut~s 2 l’aluminium
point curves) 3)Ibid 15,795 -6(1923 )( The freezing developed in France beginning in 1935 and then
point- volubility diagram of the system TNT-P icric after WWII and approved by CSE(Commission des
Acid) 3a)Ibid 15,1070-3(1923) (The freezing point Substances Explosives). Tkse expls consist of
-volubility diagram of the system Tetryl-Picric Acid) AN, a nitro-compd(such as DNN, TNT, pentolite,
3b)Nao6m, Expls(1927), 135 4)Nao6m, NG(1928), etc) with or w/o Al powder. For instance, the expl
11,261 & 324 4a)Molina( 1930),340 4b)Stettbacher 63-CSE-1949 consists of AN 67, TNT 10 & Al 21%
(1933),294,309-10 & 316 4c)M.Giua & G-Guastalla, and its CUP(power by the Fr lead block expansion
Chim & Ind 29,64T( 1933) (Study of binary systems method) is 147( PA= 100)] 14) L. F. Audrieth & D.D.
of Centrality with p-MNT; 2,4-DNT, 2,4,6-TNT; PA Sager,USP 2,482,089-91(1949) & CA 44,839-40
and Bromo-2 ,4-dinitrophenol) 4d)T .Urbafiski et al, ( 1950) [The three component expls: a)TNT/Terryl
RocznikiChem 13,399-434(1933) & C A 28,27(1934) /RDX b)Tetryl/TNT/EDNA and c)PETN/TNT
Ibid 14,239-45, 925-40(1934) & CA 29,6129(1935); /EDNA are characterized by their superior expl
Ibid 15,191-7(1935) & CA 30,2834(1936); Ibid 16, props, higher d, etc and for these reasons they are
353-65( 1936) & CA 3 1,2502( 1936); 1~,585-90(1937) recommended for use in shells, bombs and mines].
& CA 32,15 s6(1938) (Thermal analysis of various 14a)Giua,Dizionario 2(1951), 165 15)Kirk &
mixts contg nitrates, nitric acid esters and nitro Othmer 6(1951),19 & 56( Binary expls are described
compds) 5) Thorpe 4,(1940),464 5a)Davis(1943), under Explosives) 15a) Belgrano(1952),l 18-22,
353-4 & 367(SprengeI EXPIS and N2TN, NDNT, NT, 163.180-1,286 & tables 16)M.Thomas,Mp 36,133
NTN & NX expls) 5b)Bebie(1943),35 & 73 -62(1952) & CA 49, 16435-6(1955) [Discussion of
5c)A.Stettbacher, Protar 9,38 & 41(1943) 6)W.R. methods of separating components of binary mixts
Tomlinson,Jr,PATR 1360(1943); Ibid 1379( 1944); of nitrated derivs or nitrates by a solvent. From
Ibid 1402( 1944); Ibid 1414(1944); 1429(1944) & the amt of solvent just insufficient to dissolve a
Ibid 1452( 1944) (Properties of ternary mixts of known wt of sample and the additional amt requir-
HE’s) 7)A. J. Phillips, PATR l~5(l944)(Prop- ed to effect soln, the identity of the sample was
erties of ternary mixts of HE ‘s) 8)H. A. Aaronson, detd. This was verified by addrd tests, such as
PATR 1469(1944) (Properties of ternary mixts of mP, tryst form and colors obtd in acet soln with
HE’s) 8a)Anon, “Handbook of Japanese Explosive NaOH or NH3. The method was applied to the fol-
Ordnance”, OpNav 30.3M(1945) 9)L.H. Eriksen, lowing eight mixts: a) PETN/DNB b)PE TN/TNT
PATR 1506(1945) & Ibid 1623(1946) (Properties of c)PETN/DNN d)RDX/DNB e)RDX/TNT f)
ternary mixts of HE’s) 9a)Shilling( 1946),79-85, HNDPhA/TNT g)TetryI/TNT h)NGu/TNT]
90-2,95,97-9,144-7 & 240 9b)AlI&EnExpls( 1946), 17)K.Yamasue et al, JapP 2097(’54) & CA 49,2076
107 & 134 10)A.N.Campbell & E. J. Pritchard, (1955) (A binary expl prepd by nitrating a mixt of
CanadJRes 256, 183-97(1947) & CA 4 1,4647(1947) 30% naphthalene & 70% toluene with 2.5 times its
(Study of binary mixts PA-2,4-DNPh, TNT-DNPh wt of 50/50 mixed nitric-sulfuric acid at 130°,
and ternary mixt of PA-DN~-TNT) 1 l)A.N. Camp- rendered an expl with N 16.9% and mp 60° suitable
bell et al, CanadJRes 256,211-15(1947) & CA 41, for use in dynamites) 18)PATR 251O(PB No
7220(1947) (Study of binary and ternary eutectics 161270)( 1958),pp Ger 4,5 ,6,30,43-4,46-8,88,1 14,
consisting of PA, DNPh & Picramide) 12)A.N. 122,128,132,170,203,209 & 212-3 19)Anon, WAna-
Campbell & N. A. Kushnarov,CanJRes 25B,2 16-27 Iytical Methods for Powders and Explosives”,AB
(1947) & CA 4],7218(1947)(Study of binary mixts Bofor.. Nobelkrut,Sweden( 1958) 20)D.Price,Chem
of TNT-RDX, NENO-TNT and m-DNB-NENO) Revs ;9,814-15(1959)
12a)H. Ficheroulle,MP 30,98-100(1948) & CA 45,
8249( 19 Sl)(Studies of binary mixts of ethylerredi- Binder or Agglutinant is a material, such as as-
nitramine, Amm ethylenedinitramate with AN and phalt or bitumen, dextrin, starch, flour, glue,
ethylene diamine nitrate showed that they are more fossil gums, gelatin , milk sugar, pqtrolatum,
sensitive and more expensive than the Fr std expl resins, shellac, stearin, paraffin wax, sugar, syn-

—. —
 B 121

thetic org plastics, NC, etc, used to hold solid Bindone or Anhydrobisindandione (called Anhydro
substances together in a plastic mass. Binders -bis-[a.y-diketohydrinden] and other names in Ger),
are used in expls, proplnts and pyrotechnic com- Cl ~Hl ~0~, microscopic tablets, mp 206-8° (dec).
pns. Most binders serve at the same time as fuels Prepn & props are given in Ref 1. Vanags(Ref 2)
(see also Adhesives in Vol l,p A102-R and under proposed to utilize the prop of bindone to give
Bonding in Vol 2) characteristic colors with prim ary amines, for test-
Refs: l)Hackh’s(1944),127 2)H.A.Bruson & G.B. ing nitrocompds by first reducing them to amines
Butler,USP 2400806(1946) & CA 40,4526(1946) (by means of Zn+AcOH) and then adding bindone.
(Highly nitrated, vigorously combustible synthetic The test is not specific, however, for nitrocompds
resin prepd by condensing TNT with HCHO and NH3 but applies also to nitroso, azoxy- and hydrazo-
or a primary amine capabIe of forming a MeOH deriv, compds
may be used as a binding material in expI compns) Re/s: l)Beil 7,876,(484) & [839] 2)G.Vanags,
3)H.Zenftman & A. McLean,USP 2527420(1951) & ZAnalC~em 126,21-35(1943) & CA 37,6593(1943)
CA 46,2300(1952) (Nitropolystyrenes contg 9.3 to
14.4% N are recommended as binders for expl com- Binitro-,Same as Dinitro-. See under corresponding
pns in lieu of NC) 4)Kirk & Othmer 11(1953),334 parent compounds
(Binders in commercial pyrotechnic compns and in
rockets) 5) Bjorksten Research Laboratories,Inc, Biochemical or Biological Oxidation. See Bio
“Polyesters and Their Application” ,Reinhold,NY -oxidation
(1956),21-34
Addnl Refs on Binders(not used as sources of Biological, Bacteriological or Germ Warfare. See
info: under Chemical, Biological and Radiological(CBR)
a)Frankford Arsenal Rept R.445( 1943) (Stability of Warfare
cellulose-alginate-glue binder for FA70 and FA-
90A primary compns) b)S.Helf,PATR 1750(1949) Biological Oxidation. See Bio-oxidation
(Tests of expl binder compds submitted by ADL)
(conf) c)H.J.Eppig & J. D. Strachm, PATR 1801 Bio.oxidation, Biological Oxidation or Biochemi.
(1950 ](Self-hardening pyrotechnic compns) d)p~ cal Oxidation is a method for disposal of organic
chase Description PAcPDs124 (1953), 4-6(Detn of process water-borne wastes by the action of living
binder-lubricant content in R“DX) e)P .L.Nichols, organisms. Techniques for bio-oxidation may be
Jr, et al, Caltech Progress Rept NO 20*1W1953) divided into two general categories. The oldest
(Prepn of nitric ester plasticizers and resin inter- method is to pass the wastes through a stationary
mediates for composite propellant resin binders for biological bed, or trickling filter. The second metb
AN propellants) f)Ibid, No 20* 197( 1953 )( The use od (first proposed during the period of 1910-1920)
of epoxide resin binders for AN propellants) is to pass the biological growths through the wastes.
g)SFAL Rept No 54-F FI-71,PicArsn,Dover,NJ( 1954) This process is called activated sludge. Both of
(Investgn of binders for Pelleting Type III, Class these processes are described in the Ref listed
A, Photoflash Powder) (conf) h)F.H.Doe, ERDE below
TechMemo 7/M/55(1955) (plastic ProP1nt based on It must be noted that during WWII nearly all US
polyisobutene as binder) i)E.E.Mason et al,Nav expI and ammo plants used bio-oxidation for dis-
ord Rept 5461( 1957) (Prelimin~ investgn of cast- posal of some of their organic wastes. This did
able perchlorate systems and binders for ammonium not include TNT and some other expls for which
perchlorate) (conf) j)R.L. Wagner, K. G. Sheffield & no effective bacteria was found(See also under
D. E. Seeger, EDS SFAL Rept No 60, PicArsn,Dover, Waste Disposal)
NJ(1960)(Binder for RDX used in M47 Detonatcr Refi W. W. Eckenfelder, Jr & T. L. More, “Bio-Oxi-
consisting of 5,0/5 O Ca resinate/Graphite) k)B. dation”, ChemEngrg 1955( Sept), 189-202(22 refs)
Jackson,S.M.Kaye & G. Weingarten,FREL Tech
Note 40, PicArsn,Dover,NJ( 1960) (Resins other Bioxide d’hydrogene. Fr for Hydrogen Peroxide
than Laminac 4116 as binders in pyrotechnic com-
pns) l)US Military Specification MIL-B-10854(NG BIP. A cast double-base ~roplnt deveIoped at ABL.
comphor binder for pyrotechnic compns) Its compn & props are given in Propellant Manual,
SPIA/M2(1959),Unit NO 502
Binding Energy. See under Atomic (or Nuclear)
Energy; VO1 l,P A500-R Biphenic or Diphenic Acid (Biphenyl-2,2’-dicarbox-
 B 122

ylic Acid or Bibenzoic Acid) [Diphensaure; Di- patent(Ref 2). Its K or Pb salts, or the compd
phenyI-dicarbon saure-(2 .2’) in Ger]. See under Bi- itself, were proposed for use in initiators to-
phenyldicarboxylic Acids gether with PETN as a base chge. The initiat-
ing power of this compd, or its salts, was
Biphenol and Derivatives claimed to be greater than that of LA
Bipbenol, Dibydroxybipheny lor Dipbenol(called l) Beil- not found 2)E. von Herz,BritP
Dioxy-diphenyl in Ger), H0.C6H4 .C6H4 .OH. 207563(1922); CA 18, 1573-4(1924) & JSCI 43,
Several derivs are described in Beil 6,989,990, 451 T(1924)
991,993(484,485) & [960,961,962] Pentanitrobiphenol, C12H5N5012, mw 411.20,
Morzonitrobipbenol, C, ~H9N04 -not found in Beil N 17.03%. The following isomer is described in
Dinitrobipberzol, Cl *H8N206. Several isomers are the literature: 2,4,6,4’, 6’-Pentanitro-3,3’- bi-
described in Beil 6,990,992,993 phenol, (02 N)2(OH)CeH2.C6H(OH)(N02 )3, yeI
Trinitrobipbenol, C, *H7N30~ -not found in Beil grains(from dil ale), mp 248° (dec); sol in hot w
Tetranitrobiphenol, C12H6N4O10, mw 366.20, N or ale; sol in acet, ACOH or benz; nearly insol
15.30%. The following isomers are described in in eth or chlf. Was prepd by Borsche, together
the literature: with 4,6,4’ 6’-tetranitro-3,3 ‘-biphenol, on nitra-
3,5,3’, 5’-Tetranitro-2,2’- bipbenol or 2,2’-Di- tion of 3,3‘-biphenol. Its expl props were not
bydroxy-3, 5,3’, 5’-biphenyl, investigated
(02N)2(OH)C6H2.C6H2 (0H) (N02)2, grn-yel ndls Refs: l)Beil 6,(485) 2)W.Borsche, Ber 50,830
(from dil AcOH, mp 248-9°; easily sol in benz or (1917)
AcOH; diffc sol in alc or ether. Can be prepd by Hexanitrobiphenol, Cl ‘H4N60i ~, mw 456.20,
nitration of 2,2’-biphenol or by other methods. It N 18.42$%. The following isomer is described in
seems to be dimorphous; the 2nd form, prepd as the literature: 2,4,6,2’,4’, 6’-Hexanitro-3, 3*-bi-
described in Ref 2, decrepitated at 160 0. Its expl phenol or Bipicric Acid,
props were not detd (02 N)9(HO)C#.C#(OH) (N02),, lt yel ndls
Refs: l)Beil 6,990 & [960] 2) J.van Alpen,Rec 51, (from benz), mp- stable up to 270°; expl at high-
179-80(1932) & CA 26,1273(1932) er temp with evoln of flame; easily sol in w,
4,6,4’, 6’-Tetranitro-3, 3 ‘-bipherzol, lt yel ndls(from ale, acet or AcOH; diffc sol in benz, eth or
dil AcOH), mp 208.5°; sol in hot w or ale; sol in Can be prepd from 3,3‘-biphenol by sulfonation
acet, ACOH or benz; nearly insol in eth or chlf. with coned sulfuric acid followed by nitration
Can be prepd by nitration of 3,3‘-biphenol. Its with mixed nitric-sulfuric acid(?7efs 1 & 2). It
expl props were not detd forms salts, such as Potassium salt, orn-yel
Refs: l)Beil 6,(485) 2)W.Borsche,Ber 50,830 mp 1060, expl 320°; Ammonium salt,
(1917) C, ~H4N60, ~. 2NH~, orn-yeI, begins to dec at
3,5,3’, S’-Tetranitro-4, 4’-bipbenol, yel cyst(from 275 and dec rapidly at 300-5°
ACOH), mp 223°. Can be prepd by nitration of Refs: l)Beil 6,(485) 2)W.Borsche,Ber 50,832
4,4’-biphenol or by other methods. Its expl props (1917) 3)L.Mascarelli & B.Visintin,Gazz 62,
were not detd 358(1932) & CA 26,4809(1932) 4)L.Mascarelli
Refs: l)Beil 6,992,(486) & [963] 2)G.van Rom- & D. Gatti,Industria Chimica 6, No 11,7(1931) &
burgh,Rec 41,40(1922) 3)H.Hart & W. J. Detroit, CA 26,5559(1932) 5)Blatt,0SRD 2014( 1944)-
JACS 74,5214-15(1952) & CA 48,136(M(1954) (The not listed
dissociation of 3 ,5,3’,5‘-terranitro-4,4 ‘-dihydroxy-
kdphenyl in methanol) Biphenyl and Derivatives
2,2’~Di azcw3,3’adioxy’4,6,4’,6’*te*anitr*m,m’ Bipbenyl; Dipbenyl; Dip benylyl or Pbenylbenz-
lbiphenol or Bis(2~diazo*3~oxy~4,6 _dinitw)*m,m’ ene, C6H .C H ; mw 154.20, CO1 monocl trysts,
l biphenol (called sym-Tetranitro-dioxy-diphenol mp 69-70$, b; 2?4.9°, d 0.992 at 73°/40; Qc
-quinone-tetrazide or Tetranitro-diresorcin-diazo 1493kcal/mol, Qf 23. lkcal/mol (Ref 2a); insol
-anhydride by von Herz), in w; sol in alc or eth. Was first prepd in 1862

>–c+c_c> N :C—C:O
>.N02;
by Fittig. Many methods for its prepn are known
(Refs 1 & 2) [See also CA’s 43,2979b(1949);48,
02N”cac–c<o. .- 03 C–C.OH 12175 f(1954); 50,1084c; 5753i; 12922e(1956)].
mw 450.20, N 25.0170. This compd, as well as Biphenyl is one of the most thermally stable
its salts, was claimed to have been prepd by org compds. Chemically it resembles benz and
von Herz but no method of prepn is given in the can be chlorinated, nitrated, sulfonated and

. ———...—..—
 B 123

hydrogenated. Its stereochemistry is discussed Beil 5, [487]

in Ref la. BiphenyI is used chiefly as a heat Mononitrobiphenyl, Cl2H9N02, mw 199.20, N
transfer medium and as the raw material for 7.03%. Several isomers are described in the
chlorinated biphenyls(Ref 2). It was also pro- literature. Its ortho isomer has been recom-
posed as a fuel in turbojet type burners(~ef 3) mended(Ref 3) as a plasticizer for synthetic
Re/.s: l)Beil 5,576,(271) & [479] Ia)R.Adams resins, cellulose esters & ethers and other pro-
& H. C. Yuan,ChemRevs i2,261-338(1933) ducts
2)Kirk & Othmer 5(1950),145-8 2a)G.S.Parks & Re/s: l)Beil 5,582,583,(273)& [487] 2)J.Brull,
L. M. Vaughan,JACS 73,2380(195 1) & CA 45,10028 Gazz 65, 19-28( 1935)& CA 29,3589(1935)
(1951) 3)J.W.Mullen & J. B. Fenn,BritP 709,035 3)Monsanto Chemical CO,IEC 37, No 12, p 78
(1954) & CA 48,11032(1954) 4)J.M.Scarborough, ( 1945) (Props of tech grade o-nitrobiphenyl)
North American Aviation, Inc, NAA-SR-4657 Dinitrobipbenyl, Cl ~H~N204, mw 244.2o, N
(1960) (IR spectra of biphenyl)(U) 11.47%. Several isomers are described in the
Azidobipherzyl, C6H~.C6H4.N~, mw 195.22, N literature, none of them expl
21. 53%. Its ortho-deriv, CO1 trysts, mp 49-50°, Re/s: l)Beil 5,583,584(273,274) & [490,491]
was prepd from 2-aminobipheny1 as described 2)OrgSynthCollVol 2(1943), 339
in Ref 2, under Procedure A 3,3’-Dinitrobiphenyl-Lead Nitrate [called Di
Re/s: l) Beil- not found 2)P.A.S.Smith & B.B. -(m-nitro.pbmyl) Lead Nitrate by McGiIl],
Brown,JACS 73,2440(1951) & CA 46,495(1952) (02N.CeH4.C#4.N02 ). Pb(N03)z, wh trysts,
Diazidobiphenyl, N3.C6H4.C6H4.N3; mw236.23,
mp-obeglns to turn brn at 210° & blackens at
N 35.58%. The following isomers were found in 245 ; expl on rapid heating. Can be prepd by
the literature: 2, 2*-Diazidobipbenyl, tan ndls, treating tetraphenyllead with nitric acid. It is
mp 72.5-73.5°. Was prepd from 2,2’-dinitro-bi- an expl comparable in sensitivity to Tetryl and
phenyl as described in Ref 2. Its expl props about 54z as powerful as TNT(by Ballistic
were not detd(Ref 5) and 4,4*-Diazidobiphenyl Mortar Test). Its thermal stability is satisfactory
(called 4.4’-Bistriazo-diphenyl and ‘Tetrazobi- but it is appreciably hydroscopic
phenylimid” in Ger), brownish trysts, mp 127° Re/s: l)Beil- not found 2)R.McGiH,0SRD830
(Refs 1 & 4), mp 131°(Refs 2 & 3); decomp 165 (1942),21
-700; expl on rapid heating or on contact with Trinitrobiphenyl, C12H7N905, mw 289.20, N
a drop of coned sulfuric acid(Refs 2 & 3). Can
14.53%. The following isomers are described in
be prepd by treating diphenylbisdiazoniumpet- the literature: 2,4,6- Trinitrobiphenyl,
bromide with ammonia(Ref 1) or by other meth- C6~ C6H2(N02)3, It yel ndls(from ale), fiP
ods(Refs 2,3 & 4)
130°. Was prepd by heating picrylchloride with
Re/.v: l)Beil 5,585 2)Beil 5,[494] 3)FoD.
iodobenzene and copper bronze at 190-200 °(Ref
Chattaway et al,JCS 125, 1984(1924) 4)H.Bret-
1 & 3) 2,4, 2’-Trirzitrobipbenyl, (02N)C6Hg .C6-
schneider & H. Rager,Monatsh 8 ] ,970(1950) &
(OZN)C6H4.C6H3(N02 )2, lt yel prisms(from
CA 45, 7973(1951) 5)P.A.S.Smith et al,JAcs 75!
Ac@H), mp 150-1 0. Was obtained, together with
6337(1953) &CA 49,7571(1955)
2,4,4 ‘-trinitrobiphenyl, by heating 2,4- or 2,4’
Azidonitrobiphenyl, C, ~H8N402, mw 240.22,
-dinitrobiphenyl with nitric acid(d 1.5) at 100°
N 23.33%. The isomers: 2-azido-2’-nitro, mp
(Refs 1 & 3) 2,4,4’-Trinitrobiphenyl, It yel
80.5-81.5°; 2-azido-3-nitro-, mp 62.5-63.5°;
crpts(from AcOH or HN03), mp 175.5-176°.
2’-azido-4-nitro, mp 92. 5-93.5°; and 2-azido
Was first prepd by treating biphenyl with ethyl-
--5-nitro-, mp 86-7° are listed in Ref 2
nitrate in coned sulfuric acid at -5 °(Refs 1 & 2).
Re/s: l)Beil- not found 2)P.A.S.Smith & B.B.
Another method is the nitration of 2,4- or 2,4’
Brown,JACS 73,2440(1951) & CA 46,495( 1952)
-dinitrobiphenyl with nitric acid(d 1.5) at 100°
Azidodinitrobiphenyl, C12H7N5O4, mw 285.22,
(Refs 1,2 & 3) 2,4,3’-Trinitrobipbenyl, trysts
N 24.56%. The isomers: 2-azido-3, 5-dinitro-,
(from sIc), mp 137-8°; was prepd by heating 2,-
mp 118-19°; 2-azido-4, 4’-dinitro-, mp 177-8°,
3’-dinitrobiphenyl with nitric acid(d 1.5) for 3
and 2-azido-5, 4’-dinitro-, mp 174-50 are listed
mins(Ref 5) 3,4, 3’-”Trinitrobipb enYZ, trysts
in Ref 2, where their methods of prepn are given
(from acet+ ale). mp 179-80°; was prepd by heap
as Procedure B. Their expl props were not detd
ing 3,3’-dinitrobiphenyl with nitric acid(d 1.5)
Re/s: l)Beil- not found 2)P.A.S.Smifi & B*B.
for 1 hr(Ref 3) 3,3,4‘-’TrinitrobiPb enYl, Cryts
Brown, JACS 73,2440(1951)& CA 46,495(1952)
(from benz), mp 205-6°; was prepd by heating
4-Nitrosobiphenyl, C6H5.C6H4.N0, is listed in
 I

B 124

3 ,4’-dinitrobiphenyl with nitric acid(d 1.5 ) for Ber 34,2179(1901) 3)F.H.Case,JACS 64,2225
1 hr(Ref 5) and 3, $3’- Trinitrobipbenyl, solid (1942) & CA 36,6517(1942)
Wp 173-4°; was prepd in small quantity by 3,5, 3‘, 5‘-retranitrophenyl, solid(from toluene),
heating 3 ,5-dinitroiodoben zene with m-nitro- mp 228-9°; was prepd by heating with stirring a
iodobenzene & Cu powder for an hr at 270 °(Ref mixt of 3, 5-dinitroiodoben zene with Cu pdr at
4). Expl props of trinitrobiphenyls were not detd 270° for 1 xhrs. Its expl props were not detd
Refs: I)Beil 5, [493] 2)H.Raudnitz & H. Bohm, Re/s: l)Beil- not found 2)F.H.Case,JACS 64,
Ber 60 B,740-1(1927) & CA 21,1981(1922) 3)H. 1852(1942) & CA 36,5805(1942)
C.Gull & E. E. Turner,JCS 1929,495-8 & CA 23, Pentanitrobiphenyl, C, ~H5N501 o - not found
2962(1929) 4)F.H.Case,JACS 64,1852(1942) & in i3eil or CA thru 1956
CA 36, >805(1942) 5)F.H.Case,JACS 64,2225 2,4,6,2’,4’,6’-Hexanitrobiphenyl, (02N)3C6H2 -
(1942) & CA 36, 6517(1942) CGH2(N02)3, mw 424.20, N 19.81%, OB
Tetranitrobiphenyl, C , ~H6N408, mw 334.20, N to C02 -52.8%; brn trysts with 0.5
16.77%. The following isomers were found in C, H*(from toluene), mp 238° (Nefs 1 & 2); yel
the literature: -brn crysts(from AcOH), mp 242 °(Ref 5); It yel
2,4,2’,4’-Tetranitrobipherzyl, (02 N~2C6H3(N02)2, trysts with O. 5C~H8(from toluene); loses C7H8
It yel crysts(from benz), mp 163-6 ; easily sol at 140°(Ref 3); mp 263 °(Ref 6); ignites above
in AcOH or benz; diffc sol in alc or eth. Can be 320°; insol in w; SI sol in acet, ale, eth, hot
prepd by nitration of diphenyl(Refs 1 & 5), of benz, toluene or AcOH. HNBPh gives a yel
2,2’-dinitro-, of 2,4,2’- or 2,4,4’-trinitrobiphenyl, color with coned sulfuric acid and red with alc
or by other methods(Refs I & 4). Its expl props to which a drop of ammonia water or aq caustic
were not detd soda has been added. It is neutral, chemically
According to Ref 4, this compd is dimorphous unreactive toward metals and is reported to be
with rep’s 16d & 150-1° non-poisonous(Re fs 1,2 & 6). It can be compres-
Re/s: l)BeiI 5,585 & [494] 2)F.Ullmann & sed to d 1.61 at 2500 atms
J. Bielecki,Ber 34,2177(1901) 3)H.C.GUI1 & HNBPh was first prepd in 1901(Ref 2) by boil-
E. E. Turner, JCS 1929,495 4) J.van Alphen,Rec ing picryl chloride in MNB soln with Cu pdr for
51,456-7( 1932) 5) E. H. Huntress,USP 1870- a short time. The solvent is necessary in order to
627(1932) & CA 26,5579(1932) moderate the reaction, for picrylchloride
2,4,3’,4’- Tetraraitrobipbenyl, It yel crysts(from & Cu pdr expl when heated alone to ca 127 °(Ref
methanol), mp 173°; can be prepd by treating 6). It cannot be prepd by direct nitration of bi-
2,3’- or 3,4’-dinitrobiphenyl with mixed nitric phenyl; the highest nitrated product is 2,4,2 ‘,4’-
-sulfuric acid. Its expl props were not detd tetranitrobipheny l(Ref 6)
Re/s: l)Beil 5, [494] 2)W.Blakey & H.A. HNBPh is a powerful expl; its Trauzl test
Scarborough,JCS 1927,3006 & CA 22,955(1928) value is about 10% higher than for HNBPhA
2,6,2’,6’- Tetranitrobipberzyl, yel ndls(from A cOH), (Refs 6 & 7). It is more sensitive to impact than
mp 217- 18°; was first prepd in small quantity by TNB and less sensitive than Tetryl(Ref 5).
treating 2-chloro- l,3-dinitrobenzene with Cu pdr Jahn(Ref 4) patented the following expl mixt
in boiling benz(Refs 1 & 2); can also be prepd cIaimed to be suitable for loading torpedoes and
by heating l-bromo-2,6-dinitrobenzene with cop- mines: HNBPh 12, AN 80, NG 4 & flour 4%
per bronze for 2 hrs on an oil bath(Ref 3). Its Re/s: l)Beil 5,585(274) & [494] 2)F.Ullman &
expl props were not detd J. Bielecki,Ber 34,2179(1901) 3)S.prengstoff AG
Re/s: l)Beil 5,(274) 2)W.Borsche & D.Rantscheff, Carbonit,GerP 286736(1913) & CA 10,1272(1916)
Ann 379, 176(191 1) 3) J. Hawkins & S. H.Tucker, and BripP 18333(1914) & CA 10,392(1916)
JCS 1950,3288& CA 45,6619(1951) 4)C.R.Jahn,USP 1?53691(1918) & CA 12,767(1918)
3,4,3’,4’- Tetranitrobipbe nyl, yel prisms, mp 186° 5)C.F.van Duin,Rec 39,686-7(1929) 5a)Pepin
(Refs 1 & 2);, crysts(from alc+acet), mp 203-4° Lehalleur(1935), 193 6)Davis(1943),158-9
(Ref 3); easily sol in ACOH or benz; nearly insol 7)Blatt,0SRD 2014(1944) 8~ax(1957)-not listed
in Iigroin. Was first prepd by heating 1,2-dinitro 2,4,6,2’,4’,6’.Hexanitrobiphenyl Salts, The Lead
-4-iodobenzene with copper bronze at 230-50° salt, C, ~H2N601 *Pb and the Mercury salt
(Refs 1 & 2); can slao be prepd by nitration of C ,2 H2N6C)1 ~1-fg, were prepd and examined
3,4,3 ‘,-trinitrobiphenyl with mixed nitric-sulfuric during WWII in the US and were found to be less
acid(Ref 3). Its expI props were not detd powerful and brisant than PA
Re/s: l)Beil 5,585 2)F. UHmann & J. Bielecki, Refi A.H.BIatt & F. C. Whitmore,OSRD 1085

,- .———.. ——— ——
(1942),48 Acid, (02N)2C6H3 .C%H(N02 )3. COOH, wh trysts
(from benz), mp 205-6 . Was prepd by treating in
Biphenyl.4.amine. See under Aminobiphenyls; a salt-ice bath, with stirring, the 2,4,6,2’,4’-penta-
Vol l,p A19 1-L nitro-3-methylbiphenyl with fuming nitric acid,
followed by fuming sulfuric acid. The expl props
Biphenylamine. See Diphenylamine of pentanitro-compd were not investigated
Re/s: l)Beil- not found 2)H.A.Stearns & R.
Biphenyl.bis(diazoniumhydroxide) and Adams,JACS 52,2070& 2073(1930) & CA 24,3005
Derivatives (1930)
Biphenyl.bis(4.4’.diazoniumhydroxide) [called Hexanitrobipbeny lcarboxylic Acid, C, ~H4Ns0, ~-
Diphenyl-bis-diazoniumhydroxid-(4.4’) or Terrazo- not found in Beil or in CA t~u 1956
diphenyl in Ger],H0.N(~N).CGH4 .C6H4.N(~N).0H;
mw 242.23, N 23. 13%; known only in the form of Biphenyldiamine Same as Diaminobiphenyl
its salts, some of which are expl: A ntim WY
Chloride, C ,2H~(N. Cl)z+ 5SbC13+HCl; COI ndls, Biphenyldiazomethane, (C~H~ )2C:N!N, mw
mp expl violently; Boro@oride,C, *H8(N2.BF4)2; 194.23, N 14.42%, dk-red ndls(from petr ether),
crysts(from w), mp dec ca 137-138°; Lead mp 29-30°, decomp explosively ca 115°; easily
Chloride, C 12 H&l (N2.CI)2+ PbC14; orn-yel trysts, sol in most org solvents. Can be prepd by oxida-
mp expl ca 131 ; Nitrate, Cl ~HB(N2.0.N02)2; tion of benzophenonehydrazone with freshly pptd
yel-wh ndls(from w by pptn with alc & eth), mp mercuric oxide in petr ether or by other methods
expl on heating; and tetracbloroiodide, Re/s: l)BeiI 7,(226) & [358] 2)H.Staudinger et
C, ~Ha(N2.1C14 )2; yel-brn trysts, mp expl at 135 al,Ber 49,1908 & 1932-3(1916) 3)M.Busch & R.
-140°. Other props and methods of prepn of these Knoll,Ber 60,2254(1927)
and other salts are given in Beil 16,5 15,(362) &
[285] Biphenyldiazoniumhydroxide, C6H5 .C6H4.N(~N).0H,
2.Nitrobiphenyl.bis(4.4’.diazoniumhydroxide), exists only in the form of derivs. Some of them
H0.N(iN).C6H4.C5 H34N02).Nd”N]O~ mw are described in Beil 16, [283-4]
287.23, N 24.38%. Jts Antimony
Chloride salt,
C, 2H7N02(N2.Cl)2+- 2SbC13y 2HCI; yel trysts, Biphenyldiazonium Perchlorate. See under Amino-
dec on heating with w. Other props & method of biphenyls; Vol l,p A191-L
prepn are given in the Refs
Refs: l)Beil 16,(362) 2)P.May, JCS 10I 1,~035 Biphenyldicarboxylic Acid and Derivatives
(1912) Bipbenyldicarboxy lic Acid, C, ~H, 004. Several
isomers are known, of which the 2,2’- Bipbenyl-
Biphenylcarboxylic Acid and Derivatives dicarboxylic Acid, Biphenic or Dipb enic Acid
Bipbenylcarboxyiic or Pbenylbenzoic Acid(Car- (caHed Diphensaure in Ger),
boxydiphenyl), C6 H5 .CeH4 .COOH. Three isomers HOOC.C6H4.C6H4.COOH,
are known and described in Beil 9,669,67 U279, seems to be of some industrial importance. Its
280) & [463,464] prepn from phenanthrene is described in Ref 2
Morzonitrobipbeny lcarboxylic Acid, C, 3HON04. R efs: l)Beil 9,922,926,927,(401) & [655,663,
Several isomers ate described in Beil 9,670 664,665] 2)W.F .O’Conner & E.J .Moriconi,IEC
Dinitrobiph enylcarboxylic Acid, C , ~H826” N () 45,277-88(1953)
Several isomers are described in Beil ,672 & [465] Diazidobiphenyldicarboxylic Acid, Cl ~H8N~04,
Trinitro’bipbeny lcarboxylic Acid, C, ~H7N30e, m w MW 324.25, N 25.92%. The following isomer is de
333.21, N 12.61%- not found in Beil or in CA thru scribed in the literature: 4, 4’-Diazidobipbeny l-3, -
1956 3’-dicarboxylic Acid, HOOC.C6H3(N3).C6H9 (N3).COOH,
Tetranitrobipheny lcarboxylic Acid, Cl ~HGN40, o, grey-grn trysts decompg ca 165°; sol in alc or
mw 378.21, N 14.82%- not found in Beil or in CA AcOH; v diffc sol in benz & Iigroin. Was prepd
thru 1956 from 4,4’-diaminobipheny I-3,3’-dicarboxylic acid
Pentanitrobiphenylcarboxylic Acid, C, ~H5N50, z, as described in Refs 1 & 2. Its expl props were
mw 423.21, N 16.53Yo. The following isomer is not detd
known: .?,4,6, Z’,d’-pentanitrobipb eny[-j-carboxyl- Re/s: l)Beil 9,927 2)C.BU1OW & W.von Reden,
ic Acid; 2,4,6,2’, 4’-Pentanitrc-3 -carboxydipbenyl Ber 31,2578(1898)
or 3-(2’, 4’-Dinitropb enyl)-2, k 6-trinitrobenzoic Mononitrobipberzy ldicarboxylic Acid, C ,4 H9N06.
 B 126

Several isomers are described in Beil 9,925 mineral acid

Dinitrobiph enyldicarboxylic A CZ”d,C, ~H~N20a. Quilico considered the compd as the most inter-
several isomers are described in B eil 9,925 esting of all the expl compds obtained by him
Trinitrobipbeny ldicarboxylic Acid, C, ~H7Ng0i ~, during his studies of the reactions between acetyl-
mw 377.22, N 11.147.. One isomer, 4,6,4’- Trinitro- ene and fuming nitric acid. It is also listed in Vol
dipbenyI-2, 2’-dicarboxylic Acid is described in l,p A67-R as p,p’-Biphenylenebisazotrinitrometh-
Beil 9,[662] ane
Tetranitrobiphenyldicarboxylic Acid, Cl ~H6N401 ~, Refs: l)BeiI- not found 2)A.Quilico,Gazz,62,
mw 422.22, N 13.27%. The following isomers are 912ff(1932) & CA 27 1348( 1933)(Not listed in CA
described in the literature: 4,6,4’,6’- Tetranitrobi- Formula Index for 1920-46)
pbenyl-2, 2’-dicarboxylic Acid, (02 N),(HOOC)C6~-
C6H2(C00H)(N02)2, CO1 crysts(from w), melting Biphenyl Tetraozonide (called Diphenyltetraozonid
at 288-9° when heated slowly and decompg when in Ger), C ,2HI0012, O
heated rapidIy; easily sol in alc AcOH or hot W; -O’;
diffc sol in benz. Can be prepd by nitration of di- 03 03
or trinitrobipheny ldicarboxylic acid(Refs 1 & 3 ). mw 314.20, 0 50.92%; CO1 trysts, very volatiIe;
Method of prepn from methyl ester of 2-chloro-3,5 expl violently on heating. Can be prepd by treat-
-dinitrobenzoic acid is described in Ref 2(See ing biphenyl with ozone in chlf. This compd is
also Ref 4); and 2,6,2’, 6’-Tetranitrobi fibenyl-4,4’ stable in dil ethyl acet soln
-dicarboxylic Acid, (02 N)2(HOOC).C~H2.C6 H2- Re/s: I)Beil 5,579 & [482] 2)C.Harries & V.
-(COOH)(N02)2, trysts, mp 338-42°; was prepd Weiss, Ann 347(1905)
by hydrolysis of methyl 2,6,2’ ,6’-tetranitro-4 ,4’
-diphenate as described in Ref 5. Their expl Bipicric Acid. See 2,4,6,2’,4’,6’-Hexanitrobipheno1
props were not investigated under Biphenol and Derivatives
Refs: l)Beil 9,926 & [662] 2)F .Ullmann,Ann
366,88-9(1909) 3)G.H.Christis & J. Kenner,JCS Bipropellant. A rocket proplnt consisting of two
121, 618-19(1922) & 123,782(1923) 4)R.Kuhn unmixed chemical s(usually liquid) fed into the
& O. Albrecht,Ann 4s8,221-2(1927) & CA 22,413 combustion chamber separately. One of the chem-
(1928) 5)K.Mislow & R. Bolstad,JACS 77,6712 icals is a fuel(such as alcohol, aniline, hydrazin~,
(1955) &CA ~,11990(1956) etc), while the other is an oxidizer(such as liq O,
Pentarzitrobipbeny ldicarboxylic Acid, nitric acid, hydrogen peroxide or nitrogen tetr-
C14H5N5014- not found in Beil or in CA thru 1956 oxide). The energy released on combustion of
Hexanitrobiphenyldicarboxylic Acid, C14H4N601 ~, fuel operates a propulsive rocket unit
mw 512.22, N 16.41%, OB to C02 -43.7%. The R e/-s: l)Warren( 1958), 13-14 2)Rocket Encycl
following isomer .is known:2, 4,6,2’,4’, 6’-Hexa- (1959), 43-4
nitrobipherzyl- 3,3’-dicarboxylic Acid or 2,4,6,28,4:6’
-Hexanitro-3,3’-dicarboxydipbenyl, Bipropellant Rocket Engine A rocket engine that
HOOC.(02N)3C6H .C6H(N02)3 .COOH, CO1 ndls burns a bipropellant in its combustion chamber.
(from hot benz), rapidly turning yel in air; mp 292 If a fuel ignites spontaneously on coming in con-
-3°. Was prepd by oxidation of 2,4,6,2’,4’,6’- hexrr tact with an oxidizer(hypergollic propellant) there
nitro-3,3 ‘-dimethylbiphenyl with a mixt of fuming is no need for any ignition devices
HN03 & H2S04 with NazCr207 at a temp below This engine is sometimes referred to as the
30°. Its expl props were not detd bifuel rocket engine. This term is however, im-
Refs: l)BeiI- not found 2) L. H. Bock, v.v.~foyer proper because the bifuel engine identifies an un-
& R. Adams, JACS 52,2054-8(1930) & CA 24,3004 usual device where two fuels are burned in a re-
(1930) action with an oxidizer thereby consuming three
p,p’.Bi(phenylene.azotrinitromethane), liquids
(02 N), C. N: N. C6H4. C6H4.N:N. C(NO,)~ mw Refi Rocket E ncycl (1959),43-5
412.29, N 33.97%; pdr, very stable in air, mp-
expl violently ca 112°. Was prepd by Quilico (in BIRESORCINOL AND DERIVATIVES
the course of investigation of reactions betw Biresorcinol or Tetrabydroxybipb enyl (called Di-
acetyIene and fuming nitric acid) on treating Amm resorcin or Tetraoxy-diphenyl in Ger),
nitroformate and the diazonium salt of benzidine (HO)2C6H3.C6H3( OH)2. Several iromers are de-
with an amt of AcONa sufficient to eliminate the scribed in Beil 6,1163-4 & [1126,1 129]
 B 127

Dinitmbiresorcrkol, C, *H N20e. One isomer is recently(with the introduction of high-speed cam-

described in Beil 6, [1 129! eras) did it become possible to examine the
Tetranitrobiresorcinol, C, ~HGN40, ~; mw 398.20, phenomenon more closely
N 14.07%. The isomer 3,5,3’,5’-Tetrarzitro-2,6,2’,- A series of tests was made in England and
6’-tetrabydroxy- bipb enyl, trysts, mp 268°; nearly some tests were made in France
insol in w; S1 sol in rdc; sol in ether et acetate. In regard to entrapped gases, it may be men-
Can be prepd by treating 4,6-dinitro-2-diazonium tioned that Yoffe(Ref 6) confirmed the results of
hydroxide with aq KOH, followed by an acid. Its previous investigators and in addn has shown that
expl props were not detd even the adiabatic compression of the vapor of an
Re/s: l)Beil 6,1164 2)R.Benedikt & A.Hiibl, expl helps the initiation
Montash 2,329(1881) & ChemZtr 52,548(1881) In regard to the influence of grit, Capp et al
Perztarzitrobireso rcirzo~, C, *H5N50, ~- not found (Ref 7) claimed that sensitiveness to impact in-
in Beil or in CA thru 1956 creases if grit of hardness greater than 4 is pres-
Hexanitrobiresorcinol, C, ~H4N601 ~; mw 488.20, ent while Bowden & Gurton(Ref 8) claim that only
N 17.22%, OB to C02 - 32.8%. One isomer, known grit with mp higher than 400° increases the sen-
as 2,4,6,2’,4’, 6’-Hexanitro-3, 5,3’, 5’-tetrabydroxy- sitiveness of expls such as PETN, while grits
bipbenyl, consists of shiny yel ctysts, explg c a with rep’s higher than 500° are required to in-
230° w/o melting(Ref 2); expln temp given in Ref crease the sensitiveness of LA, LSt and MF.
3 is 245°; very easily sol in w. Was first prepd in The hardness of grit used in these tests varied
1884(Ref 2) by heating biresorcinoltetracetate betw 2 & 7 on the Moh scale
with fuming nitric acid; can also be prepd by Refs: l)M.Patry,Thesis( 1933 ), NancyFrance
treating biresorcinol with fuming nitric acid(Ref 2)R.G.Vines & M. F. R. Mulcahy,Natute 157,626
3). Its power by the Trauzl test is ca 95% PA (1946) 3)R.G.Vines, Ibid 160,400(1947)
(Ref 6) 4)F.P.Bowden et al, PrRoySoc 188A,311(1947)
Its Lead salt was prepd and patented in 1923 5)F.P.Bowden & O. A. Gurton,Nature 161,348(1948)
for use in initiating compns (Ref 4). It is less & CA 42,3963(1948) 6)A.Yoffe,Ibid 161,349
sensitive to friction and impact than the parent (1948) & CA 42,3961(1948) 7) J. L.Capp et al,
compd, as was detd by Rathsburg (Ref 5) TrRoySoc, 241A, 197-296( 1948)& CA 42,7983
Re/s: l)Beil 6, 1165,(574) & [1128] 2)R.Benedikt (1948) 8)F.P.Bowden & O.A.Gurton,Nature 162,
& P .Julius,Monatsh 5,178( 1884) 3)0.von Fried- 654-5( 1948) & CA 43,1982(1949) 9)F.P.Bcwden,
richs,ChemZtr 191611,975 4)W. Friederich,Chem- & O. A. Gurton,PrRoySoc 198A,35-72(1949) & CA
Ztr 1923 IV,267 5)H.Rathsburg,ZAngewChem 41 44,2244(1950) 10)F.P.Bowden & A.D.Yoffe,
1285(1928) 6)Blatt,0SRD 2014(1944), under “Initiation and Growth of Explosion in Liquids
Nitro-compounds and Solids”, Cambridge UnivPress(England)( 1952)

Birkeland.Eyde Process. See under Nitrogen Fix- BIS COMPOUNDS

ation Processes The Iatin prefix “his” meams twice or double
as does the Latin prefix ‘bin. The Greek prefix
Birth (Initiation) and Growth of Explosion in Solid “din signifies two or double groups. In attempting
and Liquid Explosives Initiated by Impact, Fric* to systematize org them nomenclature, the prefix
tion etc. High-speed cameras reveal that when liq “din is usually employed to denote the doubling
expls, such as NG or NGc, as well as many solid of simple radicals or compds, inorg or erg, attach
.
expls, such as TNT, PETN, Tetryl etc, are ini- ed to the same atom; for example, diazido, dinitro,
tiated by one of the usual methods, the expln or dinitroso, etc; SLSO diphenylamine, (C6H5)2NH;
deton originates at one or several hot spots, contg dietbanolarnine, (H0.CH2 .CH2 )2NH; and dipbenyl-
either minute bubbles of gas(vapor) or particles metbane, (C6H5 )2CH2. “Bin is used primarily to
of grit. In the case of gas, the expln is caused by denote, the doubling of a radical or molecule of
the rise in temp due to the adiabatic compression the kind when united with the loss of hydrogen;
of the gas, while in the case of grit, friction betw for example, bibenzyl, C6H5.CH2.CH2.C6H5;
the particles of grit and the surrounding expls bimalonic acid, (HOOC)ZCH.CH(COOH)2 and
causes the temp to rise bipbenyl, C6H5.C6H~. The prefix “his” is used
The fact that the presence of gas pockets or of like “di”, but before complex radicals or expres-
grit in expls causes increases in sensitivity of sions attached to a third atom or radical; for ex-
the expl has been known for a long time, but only ample, bis(cbloromethy l)-(ClCH2-)2; bisdimetb yl-
 B 128

amino-, [(CH~ )2 N-]2; and 3, S- bis(’pherzylacet yl) -amine; 1,4, 7- Triazabeptane; Diethylenetriamirze
-benzonr’trile, C6H5.CH2.C0.C6H4 (CN).0C.CH2.- or DETA, H2N.CH2.CH2 .NH. CH2.CH2.NH ; mw
C6H5. “Bis” may also be applied to complex 103.17, N 40.73%; strongly alk Iiq, bp 1098 at
molecules made up of similar halves or compds; 20mm. Other props and prepn are given in Ref 1
for example, azobis/orrnarnidine, H2N.C(:NH).N:- Bis(ß.nitraminoethl).amine; Di(ß.nitraminoethyl)
N. C(:NH).NH2; and the cyclic compds, bistetrazole, .amine; l,7.Dinitro. 1,4,7 triazaheptane or 1,7.Di.
CHN4CHN4, and bistriazole, C2H2N3-C2H2N3. nitrodiethylenetriamine,
There are some instances where common usage 02N.HN.CH2.CH2. NH. CH2.CH2.NHoN02; mw
in the literature dictates the prefix which is adopt- 193.17, N 36.26%; micro-tryst ndls, mp 215-16°.
ed. For exampIe, a compd commonly known as Can be prepd from DETA as follows:
DINA is listed, by us, as Diethanolnitramine
Dinitrate under Diethanolamine, while B is(2-nitrozY- H, N.CH, .CH, .NH.CH, .CH, .NH,
ethyl )-rritramine and Dinitroxyethylnitramine are Et.02 C.CI
given as aIternate names. In general, in the nam-
(Ethylchloroform ate)
ing and listing of “his”, “bin, add “di” compds, w
we will follow the system adopted by CA as the H~.CH, .CH2 .~.CH, .CH, .~H
compds are listed in the latest CA Index. An COZ .Et C(9, .Et C02 .Et
alternate or second name may also be used when
either can be applied without creating ambiguity 98% HNO,
Re/s: l)Hackh’s(1944),125,129 & 262 2)A.M. i
Patterson et al, “Nomenclature, Organic Com- 0, N. N.CH, .CH, .~.CH, .CH2 .~.N02
pounds”, CA 39,5875(1945) 3 )International Union to, Et co2.Et CO,.Et
of Pure and Applied Chemistry(IUPAC)”D efinitive
Rules for Nomenclature of Organic Chemistry’, Hydrolysis with 20% NaOH I
JACS 82.5545(1960) 4)C.D.Hurd,”The General followed by acidification
with HNO~ i
Philosophy of Organic Nomenclature” ,JChemEduc
J
38,43(1961)
O, N. NH.CH, .CH2 .NH.CH2 .CH, .NH.NO,
(Ref 2,pp 3 & 14)
LIST OF BIS COMPOUNDS
Bis(allyloxymethyl).propanediol and Derivatives It is a mild expl; when heated in a test tube it
2, 2- Bis(allyloxymethyl)-1, 3-prop anedioI or Diallyl- melts and decomp with a sudden puff and evoln of
pentaerythritol, fumes; when dropped on a red-hot plate it ignites
~Hz.O.~H~ immediately and burns with a yel flame(Ref 2 ,pp
HO. H, C. C. CH,. OH, mw 216.27, 0 29.59%; Iiq, bp 26-7). Its UV absorption spectra are des~ribed in
Ref 3
LH,.o.CH,
120° at lmm, d 1.o46 at 20/20°, n~ 1.4729 at 20° ; Bis(/3-nitraminoetbyl)-amine Nitrate[called Di(f3
was prepd by treating pentaerythritol in p-dioxane -nitraminoetbyl)- ammonium Nitrate by Johnson],
with allyl chloride(Ref 3) 02 N. HN.CH2.CH2 .NH~ (N03-).CH2.CH2.NH.NOZ;
2,2- Bis(allyloxymetbyl- 1, 3-prop anediol Dinitrate, mw 292.24, N 28.76%; trysts, mp 152.5-153.5°.
~H,.0.CH,.CH:CH2 Can be prepd as follows:
02 N0.CH2. .CH2.0N02 ; mw 306.27, N 0, N.~.CH, .CH, .$f.CH, .CH, .N.NO,
2 H2.0.CH2.CH:CH2 C02 .Et Co, .Et Co, . Et
9.18%, liq, d 1.191, at 20/20°, nD 1.4688 at 20°
(Ref 2); heat of combustion is given in conf Ref 2. Ammonol ysis
Its prepn is described by Evans & Gallaghan (NH, +heat)
\
Re/s: l)Beil-not found 2)ADL Rept 4(1952),
0, N. HN. CH2 .CH, .~.CH2.CH, .NH.NO,
549(C) 3)Evans & J. A. Gallaghan,JACS 75,
CO, .Et I
1249(1953) & CA 49,3811(1955)
I
l,3.(ß.aminoethanol).benzene. Same as 1,3.Bis
Hydrolysis with aq NaOH
followed by acidification !
(~-hydroxyethylamino)-benzene
with HNO~ 1
J
Bis(aminoethyl).amine and Derivatives
Oz N. HN.CH, .CHZ .NH2+(N0~–). CH,.CH2 .NH.NO,
Bis(/3-aminoetby l)-amine; Di(/3-aminoethyl)
(Ref 2,p 13)

,. —— —.—...— —.— ..—.

 B 129

On treating this compd with 98% HN03 there was prepd by adding to an aq soln of N,N’-bis(~
was obtained the explosive: -nitraminoethyl)-ethy lenediamine dihydrochloride
Bis(ß.nitroxyethyl).amine Nitrate or Di(ß.ethanol- the calcd quantity of std alkali required to form
amine).trinitrate, free amine(Ref 2,pp 21-2)
02 N0.CH2.CH2.NH2+ (NOa-).CH2.CH2.0N02; mw Its dinitrate, C~H ,~N604.2HN03, trysts, mp
258.16, N 21.71%, OB to Co. -24.8%; crysts(from 210-1 1°; expl on heating in a test tube and oc-
abs ale), mp 116-17 °(Ref 2,p-13), mp 11~.7-l-13.20 casionally ignites when dropped on a red-hot
(Ref 4); mp 120.5 °(Ref la). When heated in a test plate. Was prepd by boiling the above amine with
tube, it melts and decomp with a sudden puff & aq nitric acid, followed by cooling(Ref 2,p 22)
evoln of fumes; when dropped on a red-hot plate, Blomquist et al(Refs 3 & 5) prepd similar
it expl with a flash(Ref 2,pp 26-7). This compd compds and on the strength of their work, the
can also be prepd by nitrating diethanolamine as structure may be written as:
described in Refs 1a and 4. It was patented in 02N.HN.CH2.CH2. ~H2+.CH2.CH2.qH2 +.CH2.CHZ
Germany(Ref la) for use as an expl alone or as a N03- N03-
component of expl compositions NH.NO=
(See also Diethanolamine and Derivatives) Jone~ & Thorn(Ref 4) detd UV absorption
Bis(fl-rzitramirzoetbyl) -rzitrarnine or 1,4, 7-Tn”nitro spectra for the compd called by them 1, 10-Dinitro
-1,4, 7-triazah eptane, -1,4,7, 10-tetrazadecan e-4, 7-dinitrate, which is
02N.HN.CH2 .cH2 .N(N02).CH2.CH2 .NH.N02. evidently identical with the dinitrate described in
Attempts of Johnson et al to prep this compd Ref 2
were unsuccessful(Ref 2) Refs: 1) Beil- not found 2) J. R. Johnson,0SRD
Re/s: l)Beil 4,255 & [695] la)Dynamit AG, Rept 915(1942 ),21-2 & 26 3)A.T.Blomquist et a~
GerP 500407(1929) & CA 24,4397(1930) 2)J.R. OSRD Rept 4134(PBL 18867)(1944) 4)R.N.Jones
Johnson,OSRD 915(1942), 1-3, 12-14& 26-7 & G.D.Thorn, CanJRes 27 B,831(1949) & CA 44,
3)R.N.Jones & J. D. Thorn,CanJRes 27 B,831(1949) 2848(1950) 5)A.T.Blomquist & F .T.Fiedorek,
& CA 4Af,2848(1950) 4) J. Cason,Jr,USP 2686804 USP2485855 (1949) & CA 44,3516-17(1950)
(1954) &CA 49,2075(1955) 1,2.Bis(277.nitraminoethyI.nitramino).ethane;
1, 2-Bis(’2’-nitraminoe tbyl)-etbanedin itramin e;
Bis(aminoethylamino).ethane and Derivatives N, N’-Di(@nitramino etb yl-nitramino)-e tbane;
1, 2-Bi~?-aminoetbyIamino)-etbane; N, N’-Bis(fi 1,4,7, 10- Tetrarzitro- 1,4,7, 10-tetrazadecane or
-amino etbyl)-etbylen ediamine; N, N*- Di(fl-amino- Trietbylerzetetranitramine,
etb yl)- etbyIenediamine; 1,4,7, 10- Te trazadecane; 02N.HN.CH2.CH2 .N(N02).CH2.CHZ .N(N02).CH2-
TrietbyIenetetramine or TETA, CH2.NH.N02; mw 326.24, N 34.38%; crysts(from
H2N.CH2.CH2.NH. CH2.CHZ.NH.CHZ.CH .NH2; hot nitromethane), mp 174. 1°; was prepd by
mw 146.24, N 38.32%; liq freezing at -18 8 and chlorination of triethylenetetramine followed by
remelting at + 12°; bp 157° at 20mm or 174° at nitration of the resulting product with nitric acid
3 lmm; d 0.9817 at 15°. Can be prepd by inter- in acetic anhydride(Ref 2). Its expl props were
action of 1, 2-dibromoethane with a large excess not investigated
of ethane-l,2-diamine hydrate(Ref 4) or by ather Re/s: l) Beil- not found 2)G.N.R.Smart & G.R.
methods(Refs 1,2 & 3) Wright,JACS 70,3142(1948)& CA 43,569-70
Its Tetrap icrate, C6H, sN4 .4CGH3N307, yel
trysts, melts with decomp ca 240° (Ref 3 ,p 1354) Bis(aminoethyl)-ethanediurethane
Re/s: l)Beil 4,255 & [695] 2)A.W.Hofmann,Ber and Derivatives
23,3712(1890) 3)R.G.Fargher,JCS 117,1353-4 1,2-Bis(29.nitraminoethyl)-ethanediurethane; or 4,7
(1920) 4)J.van Alphen,Rec 55,413-14(1936) & -Dicarbetboxy- 1,4,7, 10- tetrazadecane,
CA 30,5992-3(1936) C ,2H26N404-not found in Beil or in CA thru.
1,2.Bis(2’.aminoethyl.nitramino).ethane; 1,2 1956
-Bis(2’-aminoetbyl)-etbanedinitramine; N,N’-D i l,2aBis(2’.nitraminoethyl)~ethanediurethane;
(fl-aminoetbyl)- etbylenedinitramine or 1, 7-D initro- N, N’-Di(/3-nitramin oethyl)-etbylene diurethane
1,4,7, 10-tetrazadecane, or 4, 7-Dicarbetboxy- 1, 10-dinitro- 1,4,7, 10-tetraza-
H2N.CH2.CH2(OzN) .N.CH2.CH2.N(N02 ). CHz.CH~ decane,
NH2; mw 236.24, N 35.58%; pale yel crysts(from
w), mp 242-242 .5 °(dec); expl when heated in a 02N.HN.CH2 .CHZ .I$ CH2CH2—N.CH2 .CH2 ,NH.N02;
capillary; ignites when thrown on a red-hot pIate; C02.C2H5 t02.C2H~
 B 130

mw 380.36, N 22. 10%; wh crysts(from methanol), -Di(amino ethyl)-urea (called sym-Di [amino-athyl]
mp 92-4 °(dec); ignites and burns with yel flame -harnstoff in Ger),
when dropped on a red-hot plate. Can be prepd H3C, CH3
from bis(aminoethylamino)-ethane through a CH.HN.CO.NH.CH~ ; mw 146.19, N
series of reactions indicated in Ref 2,pp 15-18 or H2N” \NH2
by treating N, N’-bis(~-nitraminoethyl)-ethylene- 38.33%, crysts(from eth), dec by w at 40 ~ was
diamine dissolved in aq NaOH with ettiylchloro- prepd by interaction of acetaldehyde, ammonia ad
formate, C1.C02.C2H5(Ref 2,P 25). b behavior and urea(Ref 2)
toward heat is given in Ref 2,p 26 and its UV N, N’-Bis(,9-nitraminoethy l)- N, N’-dinitraurea,
absorption spectra in Ref 3 HC CH3
Treatment of the above compd with 98% nitric 3\
CH.(02N)N.C0.N(N02 ; )CH<
acid as indicated in Ref 2,p 19, resulted in for- 02N.HN’ NH.N02
mation ok mw 326.20, N 34.35%. This expl compd is described
1,2..Bis(2'.nitroxyethyl).ethanediurethane; in conf Aerojet General Corp Rept No 131, Azusa,
3, 6-Dicarbetbo.ry - 1, 8-dinitro.~y-3, 6-diuzaoctane Calif
07 sym-Di(~-ethanol)- etbylenediurethune Di- Refs: l)Beil- not found 2)A.M.Paquin,Angew-
nitrate, Chem 60A,269(1948) & CA 43, 1782( 1949)
02N0.C~.CH#CH2.CH2 .~.CH2.CH2.0N02;
C02.C#5 C02.C2H5 Bis(aminoguanidine)-l,6-dinitro-2-(aminoguanyl)
mw 382.33, N 14.66%; trysts, mp 192-192 .5 °(dec) -biguanidine. See Vol l,p A214-R to A215-L
ignites and burns rapidly with a yel flame when
dropped on a red-hot plate(?ef 2,? 26) Bis(aminoguanidinium)-1,6-dinitrobiguanidine. See
Refs: l)Beil- not found 2)J.R.Johnson,OSRD Vol l,p 214-R
915(1942),15-19 3)R.N. Jones & G.~.Thorn,Can-
JRes 27 Bj832 & 834(1949) Bis(aminoguanyl)-tetrazene. Same as Di(amino-
guanyl)-tetrazene. See l-Aminoguanyl-4-am ino-
Bis(aminoethylamino)-propane and Derivatives guanyl-tetrazene under Guanylaminoguany l-tetra-
1,3-Bis(2’-aminoethylamino)-propane; iV,N’-Bis(@ zene
-aminoe tb yl)-propane diamine or N, N‘- Di(@-amino-
eth yl)-propanediamine, Bis(aminomethyl)-propanediamine and Derivatives
H2N.CH2.CH2.HN.CH2 .CH2 .CH2 .NH.CH2.CH2-N~; 2,2- Bis(aminometbyl)- 1, 3-propanediamine; Tetrakis
CO1 liq, bp 286-7° at atm press; was prepd from (aminometbyl)-methane; Tetraaminotetrametbyl-
1,3-dibrornopropane and 1,2-diaminoethane in abs methane or Pentaerythrityltetramine, C(CH2 .NH2)4;
ale; with acids it forms salts, such as Picrate, mw 162.19, N 34.55%. Its monohydrate is a yel
yel trysts, mp 223° (indefinite) (Ref 2) viscous liq boiling at 278-820; can be prepd by
1,3.Bis[(29.nitraminoethyl).nitramino].propane; heating for 8 hrs at 1600 tetrakis(bromomethyl)
N, N’-Bis(~-nitraminoet byl)propanedinitramine -methane with coned ammonia in ale, in a closed
or N, N’-Di-(nitraminoetby l)-propanedinitramine, tube(Ref 2). Its Picrate is a yel pdr, decompg at
0ZN.HN.CH2.CH2. (02 N)N.6H2.CH2.CH2 .N(N02} 206-8°
CH2.CH2.NH.N02; mw 340.26, N 32.94%. This 2,2-Bis(nitraminomethyl)-1,3-propanedinitramine
compd, undoubtedly an expl, was probably prepd or Pentaerythrityltetranitramine,C(CH2.NH.N02)4;
by someone on nitration of bis(aminoethylamino) mw 312.21, N 42.2970, OB to C02 -41.0%s This is
-propane, but it is not described in the open lit- evidently a powerful expl. Some of its props are
eratur e listed in Ref 3, which is conf. Its description is
Re/s: l)Beil- not found 2)J.vsn Alphen,Rec 55, not found in the open Literature
835(1935) 3)Blatt,0SRD 2014(1944} not found Refs: l)Beil- not found 2)J.van Alphen,Rec 57,
267( 1938) & CA 32,4546(1938) 3)ADL,PureExp1-
N,N'-Bis(ß-aminoethyl)-ethylenediamine. See
Compds,Pt 4(1954),586(C)
Bis(aminoethylamino)-ethme
Bis(anilino)-anthraquinone and Derivatives
N,N'-Bis(ß-aminoethyl)-propanediamine. See B is- Bis(anilino)-antbraquinone or Dianilino-antbraqui-
(aminoethylamino)-propane none, C26H, ~N202. Four isomers are described
in Beil 14, 199,205,(462,468) & [99,112,117]
Bis(aminoethyl)-urea and Derivatives
Bis(mononitroanizinoJ- antlwaquinone,C 26H, ~N40e.
N, N’(or 1, 3-Bis [fl(or 1)-amino etbyl] -urea or sym
 B 131

One isomer is described in Beil 14,199 CI-$ .NH.C~H4.N02; orn-red solid, mp 190-2(Ref
Bis(dinitroanilino) -antbraquinone, C26H, ~N~O ,0. l,p 696 & Ref 3,P 543)
not found in B eil 1,2- Bis(3-nitroanilino)- ethan e, yel-red trysts, mp
1,5-Bis(2,4,6-trinitroanilino)*anthraquinone;1,5 206-8°(Ref l,p 710)
-Bis(picrylamino)-antbraquinone or 1, -5-Dipicryl 1, 2- Bis(4-nitroanilino.J- etbane, yel-brn solid, mp
-diaminoantbraquinone [called 1.5-Bis(2.4.6-tri- 216°(Ref l,p 726 & Ref 3,p 544)
nitro-aniline)-anthrachi non or 1.5-Bis-pikrylamino 1,2-B is(2’, 4’-dinitroanilino)- ethane, (02N)2C6H~
-anthrachinon in Ger], NH.CHZ.CH2.NH.CGH3 (N0 ) ; mw 392.28, N
82
21.43%; yel trysts, mp 313 ; can be prepd from
/cO\
‘02 N)3c6H2”NH”c6H3\ /C6H3.NH.CGH2(N02~; 2,4-dinitrochlorobenzene & 1,2- diamino-ethane
co (Ref 1,p 757& Ref 3,p 545)
mw 660.42, N 16.97%; orn-red ndls(from nitrobenz ); l,2-Bis(2’,4’,6’-trinitroanilino)-thane; N, N’.Di.
mp dec above 3400’; forms a brn vat in alkaline picryl- etbylenediamine or N, N’-Bis(2, 4,6-trinitro-
hyposulfite, which produces dk-grn shades on pbenyl-amino)-etbane,
cotton; was prepd from 1, 5-diaminoanthra quinone (02N)3C6H2.NH.CH2 .CH2.NH.CGH2(N02 )3; m w
and picryl chloride in boiling nitrobenzene 482.28, N 23.24%; trysts, mp 230°; dec at higher
Re/s: l)Beil 1.4,(468) 2)C.Seer & R. Weitzenbo+ temp; burned wio expln when heated on a Pt foil
Monatsh 31,376(1910) & JCS 98 1,571(1910) in a flame; SOI in hot benz; insol in alc or eth;
can be prepd by heating equimol quantities of
Bis(anilina)-azobenzene and Derivatives picrylchloride and 1,2-diaminoethane in alc
Bis(arzilino)-azoberzzene, [C6H5.NH.C6H4.N:12; Re/s: l)Beil 12,696,710,726,757,770 & [412]
mw 364.43, N 15.38%. This compd, although not 2)K.Jedlicka,JPraktChem 48,204( 1893)
found in the literature, may be considered as 3)A.Schouten,Rec 56,343-5(1937)
the parent compd of its dinitro deriv described l,2-Bis(2’,4’,6’-trinitronitranilino)-ethane;
below N. N’.Dipicryl-ethylen edinitramine;
N, N’-Bis(2,4,6
Refs: l)Beil- not found 2)CA- not found -trinitrophenyl- nitramino)-etbane; N, N’-Bis(2,4,6
3,3’-Bis(2,4-dinitroanilino)-azobenzene[called -trinitrophenyl)- ethylene-dinitramin e; 2,4, 6- Tri-
(2.4-Dinitro-diphenylamin)-<3 azo-3>- (2 ‘.4’ nitro- 1,3, S-tris(metbyhritramino)- benzene; 2,4,6, -
-dinitro-diphenylamin) in Ger], [(02N)2C6H& 2’, 4*, 6’-(Hexanitrodiph enyl)-etbylene-dinitramin e;
NH.C6H4 .N:]2 ; mw 544.43, N 20.58%; golden-yeI Bitetryl or Ditetryl; Its British name is Octyl
ndls(from pyridine), mp 285°; sol in hot pyridine [also called N, N’-Dinitro-N, N’.bis(2,4, 6.trinitro.
and in benzoic acid ethylester; insol in other pbenyl)-etbylenediumine; Octanitroethylenedi-
SOIVS; was prepd by the condensation of 3-amino pbenylamine and Bis-N(2’,4’,6*-trinitropbenyl)
-3 ‘-(2 ,4-dinitroaniIino)-azobenzene with 4-chIoro -1, 2-dinitraminoetbane],
-l,3-dinitrobenzene (02N)3C6H2.N(N02 ). CH2.CH2.N(N02). C6H2(NOJ3;
Refs: l)Beil 16,306 2)K.Brand,Ber40,3338 mw 572.28, N 24.48%, OB to CO= -44.7%; It yel
(1907) & JCS 92 I, 801(1907) fine crysts(from acet or nitroben~), mp 218-22°
Bis(anilino)-ethane and Derivatives (dec) for the pure and 206-7° for tech subs~ sol
1,2. Bis(N. aniline)- etbane; Bis(N-metbylamino. in nitrobenz; SI sol in acet or et acet; insol in w,
benzene; a, fLDianilino- etbane; 1, 2=Bis(ph enyl- ale, eth, benz, etc. Several methods for its prepn
aminob etbane or N. N’-Dipbenyl. etbylenediamine, exist but most of them give impure products. For
CgH .NH.CH2.CH2.NH. C6H5; Ifts(from ale), mp prepn of the pure compd, Schouten(Ref 3,p 546)
64. 58; easily SOI in alc & eth; was first prepd in recommends nitration of 1, 2-bis(2’,4’-dinitro-
1859 by Hofmann and since then by many others; aniline)-ethane or 1,2-bis(2’,4’ ,6’-trinitroanilino)
Bennett(Ref 2) prepd it by heating ethylene- -ethane with abs nitric acid. More economical
chIoride with aniline, while Schouten(Ref 3) used seems to be the method mentioned in Blatt(Ref
1,2-dibromoethane and aniline 10, under N, N’-Dipicrylethy lenedinitramine),
When nitrated, it yields various-stage nitro which involves condensation of etbylenediamine
compds, up to the Bitetryl (called by Brit Ditetryl) with picryl chloride(yield 89%), followed by nitra-
which is a HE tion of the resulting product with 99% nitric acid
Refs: l)Beil 12,543,(282) & [287] 2)G.M.Benne t t, at 25°(90% yield)
JCS 115,577(1919) 3)A.E.Schouten, Rec 56, Explosive and other properties of B itetryl: Ex-
541-7(1937) & CA 31,5335(1937) p~osion Temperature- decompn and no expln up
1, 2. Bis(2’-nitroanilino)- ethane, 02N.CeH4 .NH.CHZ - to 360°, but expl when heated rapidly in a flame;
 B 132

Heat of Combustion Q: 1622.6kcal/mol; Hygro- 2) CA- not found

scopicity at 25° & 100% RH- gains 0.04%; NrN’.Bis(3,5dinitro-4-aniIinophenyl)urea[called
impact Sensitivity- FI 36% PA; comparable to N. N’-Bis-(3 .5-dinitro-4-anilino-phenyl)-h arnstoff
PETN; Power, by Ballistic MO~SI 123%TNT; in Ger], [C6H~.NH.C6H2(N02 )2. NH.]2CO; mw
Power by Trauzl Test 114%PA and 130%TNT; 574.45, N 19.51%; red Ifts(from glac ACOH+ w),
Thermal Stability at 135°- not acid and no mp 252 °(dec); was prepd by heating 3,5-dinitro-
expln in 300 min(Refs 5,7,8,9 & 10) benzoylazide with glac ACOH. Its expl props
Use-s: Was proposed by Cox(Ref 5) for use as a were not investigated
base chge in blasting caps Re/s: l)Beil 13,[60] 2)H. Lindemann & W.Wessel,
Bitetryl prepd in France after WWII at the Ber 58,1228(1925) & JCS 128 1,1099(1925)
Poudrerie de Sorgues(mp 2 14°) and examined
(after purification) by M6dard et al at the Bis(anilino)-propane and Derivatives
Laboratoire Central des Poudres, had the fol- 1, 3-Bis(anilino)-p roparze; 1,3-B is(pbenylamino)
lowing props(Ref 11): mp 114 °(dec) for tech and -propane; a, Y-Dianilino-propane or N, N’-Dipbenyl
226. 5°(dec) for pwified material; d(max compres- -trim ethylenediamine,
sed) 1.70; CUP(Fr Trauzl Test) 11570PA; sen- C6H5.NH.CH2.CH2 .CH2.NH.C6H5; mw 226.31,
sibility 5 l’amorce( sensitivity to initiation} 5 Og N 12.38%; trysts, mp 40-1°, bp 244-5° at llmm;
cartridge of d 1.10 to 1.70 required 0.30g MF to sol in many org SOIVS and nearly insol in w. Was
assure complete detonation; sensibility au choc first obtd as the sulfate by Hanssen(Ref 2) and
(sensitivity to impact)- comparable to Tetryl; its base was obtd by Scholtz(Ref 3) as an oil
vitesse de detonation (velocity of detonation), (apparently in the impure state) on treating tri-
detd by the Dautriche method- 5600m/s at d 1.0, methylenebromide with aniline. Veer(Ref 4) prepd
6450 at d 1.40, 7350 at d 1.60 and 7250 at d 1.70 it in the pure state by treating aniline with 1,3
(for tech sample, mp 114°) -dibromopropane
M6dard also examined several binary md ter The following nitro derivs of this compd are
nary mixts contg Bitetryl, such as: a)50-50-Bi- known:
tetryl/TNT- a cast HE, d 1.48-1.50, vel of deton 1,3- Bis(2’-nitroanilino)-propane$
7100 to 7400m/s b)50/30/20-Bitetry l/Ethyltetiyl- 02N.C6H4.NH.CH2, CH2.CH2.NH.C6H4 (N02}
/TetryI, a castable, plastic HE, d 1.58; it could mw 316.30, N 17.71%; orn ppt; was prepd in 33.6%
not be initiated by as much as 2g of MF, but re- yield by heating an alc soln of a mixt of o-chloro-
quired a compound detonator for complete ini- nitrobenzene and l,3-diaminopropane in a sealed
tiation tube for 8 hrs at 140°. On nitration it gives the
Re/s: l)Beil 12,(371) & [426] 2)G.M. Bennett, expl Metbylene Ditetryl (see beIow)(Ref 4,p 1000)
JCS 115,576(1919) 3)A.E.Schouten, Rec ~, 1,3-Bis(4-nitroanilirzo)-p ropane, yel trysts, mp
541-7 & 871(1937) 4)G.Desseigne,MP 28,156 196°; was prepd in 19% yield by heating p-nitro-
(1938) 5)R.F.COX,USP 2 125221(1938)& CA aniline and l,3-dibromobenzene in a paraffin bath
32, 7728(1938) 6)R.C.Elderfield,0 SRD 158 at 1500 for 5% hrs. It yields the expl Metbylene
(1941 ),8 7)R.McGill,OSRD 830(1941),26 Ditetryl when nitrated(Ref 4,p 1001)
8)G. B. Kistiakowsky,OSRD 702(1942) 9)A.H. 1,3- Bis( 2’,4’-dinitroanilino)-propane, (02 N)z -
Blatt & F. C. Whitmore, OSRD 1085(1942),47 10) C6H3 .NH.CH2.CH2.CH2 .NH.C6H3(N02)2; mw
A. H. Blatt,OSRD 2014(1944)- listed in two Places: 406.31, N 20.6 To; yel trysts; was prepd by
as N, N’-Dipicrylethy lenedinitramine and as 2,4,- heating equimol quantities of 2 ,4-dinitrochloro-
6,2:4’ ,6’-(Hexanitrodipheny l)-ethyIenedinitram ine benzene and 1, 3-diaminopropane in alc on a
ll)L,M;dard,MP 33,47 & 52-5(1951); CA 47, water bath for 2 hrs. It yields the expl Metbylene
5685(1953) 12)Sax(1957)- not found Ditetryl when nitr~ted(Ref 4,p 1001)
1,3.Bis(2’,4’,6’-trinitroanilino)-propane or 1,3
Bis(aniIinophenyl)-urea and Derivatives -Bis(2’, 4’86’- trinitropbenylamino)-p ropane,
N, N’.Bi~4-arzilinopb enyl)-urea, (02 N), C6H2.NH.CHZ.CH,. CH,.NH.C6H2(N0,),;
[C6H5.NH.C6H4.NH.12CO; mw 394.46, N 14.20%. mw 496.31, N 22.58%, OB to C02 -77.3%; yel -
This compd, although not found in the literature, Ifts; mp 199°; expl at higher temp; sol in acet or
may be considered the parent compd of its dinitro nitrobenz; sparingly sol in alc, petr eth, chlf or
deriv described below CC14; insol in eth or w; was prepd by interaction
Re/s: l)Beil- not found{ The N, N’-Bis-(2-anilino- of alc soln of equimol quantities of picryl chloride
phenyl)-urea is described in Beil 13,[17] ] and l,3-diaminopropane. It yields Methylene D i-
 B 133

tetryl when nitrated(Ref 4,p 1001) alc soln of bis(a-chloro-4-nitro-benzylidene).azine

l,3-Bis(2',4',6 '-trinitro-N-nitranilino).propane; with Na azide. As a by-product of this reaction,
Methylene Ditetryl; or 1, 3- Bis(2’, 4’, 6’-trinitro. there was obtained a small quantity of a product
~henyl-nitramino)-propane[called N,N’-(Hexanitro- which exploded violently ca 149°. Its structure
diphenyI)-propyIene- l,3-dinitramine by Blatt], was not established(Ref 2,pp 327 & 335-6)
(02 N)3C~H2.N(N02).CH2 .CHZ.CH2.N(N02), C6H< Re/s: I)Beil- not found 2)R.Stol16 et al, JPrakr-
(N02)3; mw 586.31, N 23.89%, OB to C02 -5 1.8%; Chem 137,327 & 335-8(1933) & CA 27,4233(1933)
pale yel crysts(from alc+acet), mp 199-201°; sol
in boiling acet; insol in w, ale, eth, pert eth, Bis(a-azidobenzylidene)-hydrazine( called D ibenz-
benz, toluene, chlf or CC14; the pure product can hydrazidazid in Ger),
be obtd by nitrating any of the above nitro compds C6H5.C(N3):N.N: C(N3).C6H5; mw 290.28, N
with abs nitric acid(Ref 4,pp 1OOO-1); the tech 38.60%; long, fine ndls(from Cclq), mp 139°(dec),
product (mp ca 189° ) can be prepd by two-stage expl when heated in an open flame; readilY SOI in
nitration of 1,3-bisi(anilino)-propane as described chlf, CCIa, Iigroin or hot benz; mod sol in warm
in Ref 4,p 997. Its expl props were not detd eth; diffc sol in MeOH or ale; insol in w; was
Refs: I)Beil ]2,548 2)A.Hanssen,Ber 20,781 prepd by treating bis-(a-chlorobenzylidene)-hydra-
(1887) 3)M.Scholtz,Ber 32,2251(1899) 4)W.L. zinc with 2 mols of Na azide in MeOH and boiling
Veer,Rec 57,988, $197,1000-2 & 1013(1938) for 16hrs in a C02 atm
5)Blatt,0SRD 20 14( 1944) Refs: l)Beil 9,[219] 2) R. Stoll= & A. Netz,Ber
55, 1301(1922) & CA 16,3899(1922)
Bis(5-ary1-2’-tetrazolyl)-formimine,
Ar.$.N-~-~—~-N= $.Ar; class of compds; 3,4-Bis[(azidoformyl)methyl]-hexanedioyl Azide,
N= N NH N=N Cl OH ION, ~oa. A name given in CA 5th Decennial
was discussed by R. L. Scott et al in JACS 75, Formula Index, p 555F for the compd called by us
53o9- 12(1953). Nitrated derivs of these compds as /3 ,/3’-B is(carbo”xym ethyl)-adipic A a’d T etra-
might find use in expl compns or in proplnts azide or Etbane- 1, 1,2, 2-tetraacetic Acid Tetra-
azide. See under Ethane-1,1,2,2-tetraacetic Acid
Bis(azidobenzylidene)-azine and Derivatives
Bis-(a-azidobenzylidene)-azine I called Bis-[a Bis[a-azido-3(or4)-nitrobenzylidene]-azine. See
-azido-benzyliden] -hydrazin or Dibenzhydrazid- under Benzaldehydeazine
azid in Ger], C6H5.C(N3):N.N: C(N3).C5H5, mw
290,28, N 38.60%, ndls(from CC14) having an Bis-(azidothioformyl)-disulfide (called A zz”docarbon-
odor of benzonitrile; mp 139 °(dec); expl on heat- disulfide by Audrieth and Bis-azidothioformyl-di-
ing over a flame; sol in chlf, CC14, Iigroin or hot sulfid or Azidoschwefelkohlenstoff in Ger),
benz; diffc sol in methanol or alc but more sol in N3.C(:S).S.S.C( :S).N~, mw 236.31, N 35.57%; wh
warm eth; insol in w. It can be obtained in addn solid; rep-detonates with great violence >40° or
to other products by the reaction of bis-(a-chloro- when subjected to shock; unstable even at RT;
benzylidine)-azine with 2 moles of NaN3 in boil- v S1 sol in w(O.03%); SI sol in benz or CS2; sol
ing methanol and in a COZ atm. Other props are in methanol, ethano~ ether, CC14 & xylene; v sol
given in Refs 1 & 2 in acet & et acct. Can be prepd by treating azido -
Re/.s: l)Beil 9, [219] 2)R.Stol16 & A. Netz,Ber dithiocarbonic acid (see Vol l,p A632-L) or its
55,1301(1922) alkaline salts with an oxidizing agent, such as
Bis(a-azido-nitro-benzylidene)-azine, iodine in K I soln, H202, KMn04 etc. Only very
0.#.C6H4.C(N3): N. N: C(N3).C6H4.NOz, mw small quantities(not mote than lg) must be prepd
380.29, N 36.83%. TWO isomers are known: at a time and stored for not longer than 48hrs in
Bis(a-azido-3-nitro- benzylidene)-azine( called a desiccator over PZ05. Explns often occur d-
Di-m-nitrobenzhy drazidazid in Ger), fine yel ing its prepn and handling. It is a more violent
trysts, explg mildly ca 156°; fairly sol in chlf; expl than azidodithiocarbonic acid(Refs 1,2 & 3 )
difficultly sol in eth or ale. Was prepd by treating A violent expln takes place when bis-(azido-
an alc soln of bis(a-chloro-3-nitro-ben~lidene) thioformyl)-disulfide is treated with bromine or
-azine with Na azide(Ref 2,pp 327 & 337-8) ammonia(Ref 1)
and Bis(a-azido-4-nitro-benzylidene)-azine(c ailed Refs: l)Beil 3,[160] & { 357] 2) L. F. Audrieth,
Di-p-nitrobenzhydrazidazid in Ger), red-yel trysts ChemRevs 15,197(1934) 3)InorgSynth 1(1939),
explg mildly ca 161 0. Was prepd by treating an 82-4
 B 134

Bis(benzalaminoguanidine)-l,6-dinitrobiguanidine. 4,4’-Bis(2,4,6-trinitrobenzeneazo)-azoxybenzene
See Vol l,p A215-L or 4,4’- Bis(2, 4, 6-trinitroph enylazo)-azoxybenze
ne,
[(02 N), C6H2.N:N.C6H4 .I,(N,o); mw 676.44, N
Bis(benzeneazo)-azobenzene and Derivatives 24.85%; dull brn ndls, mp expl ca 321° with a
Bi~benzerzeazo)-azobenz ene or Bis(pbenylazo) flash; was prepd by reacting 2,4,6-trinitro-phenyl-
-azoherzzene[ called 4,4’ -Bis-benz o Iazo-azobenzol hydrazine with p-benzoquinoneoxime in aq alc
or Bis-(4-benzolazo-pheny l)-diimid in Ger], HCI, followed by boiling with glac ACOH to effect
[C6H5.N:N.C6H4. N:12; mw 390.’43, N 21.53%; red conversion
flake s(from benz or toluene), mp 2290; on rapid Re/s: l)Beil 16, [341] 2)W.Borsche,Ber M,1290
heating becomes a dk-red liq at ca 235°; other (1921) & JCS 120 I, 625(1921)
props and prepn are given in Beil 16,86,(232) &
[301 Bis(benzeneazoxy)-azoxybenzene and Derivatives
4,4’-Bis(4-nitrobenzeneazo)-azobenzene or 4,4’ Bis(benzeneazoxy )-azoxybenzene; B is(pbenylazog)
-Bis(4-nitropbeny lazo)-azobenzene, -azoxybenzene (called 4.4’ -Bis-benzol azoxy-azoxy -
[02N.C6H4.N:N.C6 H4.N:12; mw 480.43, N 23.3374 benzol in Ger), [C6H5(N20).C6H4 .]2(N20~ mw
orn-brn ndls(from SOIV naphtha) or garnet-red lfts 438.43, N 19. 17%. The 4,48-B is deriv exists in
(from xylol or MNB), mp 285-294°; diffc SO1 in two forms: higher melting /orm, golden-yel trysts
most org SOIVS; was prepd by heating 4-nitroso-4’ (from benz or petr eth), mp ca 230°, becomes a
-nitrohydrazobenzene with dil NaOH at 100° or thick, viscous liq dec at 265°; and lower melting
with SOIV naphtha; and from 4,4’- dinitrohydrazo- form, copper-red flakes(from benz), mp 223°.
benzene by heating with dil NaOH at 100° or Other props and methods of prepn are given in
with alc in a sealed tube in atm of N at 170°. Beil 16,(381) & [324]
Other props are given in the Refs Note: Bis(rnononitropbeny lazoxy)-,C24H ,6 Ne07;
Refs: l)Beil 16,(232) 2)K.Ueno & S. Akiyoshi, Bis(dinitropheny lazoxy)-, C24H1 *N, 00,, ; and
JACS ~6,3668(1954) & CA 49,10906(1955) Bis(trinitropbeny lazoxy)-azoxybenzene,
Note: Bis-dinitro. CZ4H ,4NI 008 or Bis-trinitro- c24H12N12015J Derivatives were not found in
pbenyzazo, C 24 H 1zN 1z“l .2, ‘e~i~ati~es were not Beil or in CA thru 1956
found in Beil or in CA thru 1956
4,5-Bis(benzoyl)-l,2,3,6-dioxadiazine. Same as
Bis(benzeneazo)-azoxybenzene and Derivatives 4,5-Dibenzoyl-l,2,3,6-dioxadiazine
4,4’ -Bis(benzeneazo)- azoxybenzene or 4,4*-B is-
(pherzylazo)-azoxy benzene (called 4.4*-B is-benzol- Bis(benzoyl)-hydrazine and Derivatives
azo-azoxybenzol in Ger),[C6H5 .N:N.C6H4.]Z(N20); Bis(benzoyl)-hy drazine or 1,2- Dibenzoyl- hydrazine
mw 406.43, N 20.68%; orn-yel ndls(from glac (called N.N’-Dibenzoyl-hydrazin in Ger),
ACOH) and yel trysts or red Ifts(from benz), mp C6H5.C0.NH.NH.C0 .CGH5; mw 240.25, N 11.66%;
215-2 18°; other props and methods of prepn are compd is dimorphic, existing in two tryst forms:
given in Beil 16,658,(394) & [341] very fine ndl s(from boiling alc or AcOH) and
4,4’- Bis(2-nitrobenzeneazo)- azoxybenzene or 4,4’ monoclinic prisms, both forms have mp 237-241°.
-Bis(2-nitrophenylazo)- azoxybenzene, This compd forms numerous tryst salts; its prepn
[02 N. C6H4.N:N.CGH4.12 (N20); mw 496.43, N and other props are given in Beil 9,324,(131) &
22.57%; dk-yel ndls, mp darkens and dec ca 258° [2 16]
without melting; insol in common org SOIVS; other N,N’-Bis(nitrobenzoyl)-hydrazine[called N.N’
props and methods of prepn are given in Beil 16, -Bis(nitro-benzoy l-hydrazin in Ger] ,
658 [02N.C6H4.C0.NH-I z; mw 330.25, N 16.97%;
4, 4*-B is-(2, 6-din itrobenzeneazo)- azoxybenzene or three derivs of this compd exist: Bis(2-nitrobenz-
4,4’- B is(2, 6-dinitrophenylazoh azoxybenzene oyl)-bydrazine, ndls(from NB ) or pltlts(from
[(02N)2.C6H,.N:N. CGH4.12(N20); mw 586.43, N AcOH), mp expl mildly on heating in a flame(Ref
23.89%; orn-yel ndls, mp 255.6°; diffc sol in 1); Bis(3-nitrobenzoy l)-hydrazirze, Ifts or ndls
common org SOIVS; was prepd from benzoquinone (from alc or AcOH), mp 242°(Ref 2); and Bis-
-l,4-oxime-2,6-dinitrophenylhydrazone by treat- (4-nitrobenzoyl)-hydrazine, yel ndls, mp 291°
ment with dil NaOH. Its expl props were not in- (Ref 3). Other props and methods of prepn of
vestigated these isomers are given in the Refs
Re/s: l)Beil 16,(394) 2)W. Borsche & D. Rant- R efs: l)Beil 9,375 & [247] 2)Beil 9,388
scheff,Ann 379,174(1911) & JCS 100 I, 331(1911) 3)Beil 9,400 & [274]

—— .. . —— ———
 B 135

N,N’-Bis(3,5-dinitrobenzoyl)-hydrazine[ca11ed 565,8 & 18(1949)

N. N’-Bis-(3.5-dinitrobenzoyl)-hydrazin in Ger] , 1, l‘-Bis(p-nitrobenzoy lperoxy)-dicycIobe.cy lper-
[(02N)2C6H3,C0. NH-IZ; mw 420.25, N 20.00%; o.ride, C26H2aN201 ~. This compd, probably expl,
yel pdr, mp 276°; sol in alkalies and in coned is not described in the literature, but it seems.
H2S04; diffc sol in alc or ACOH; in sol in w or that it may be prepd by treating bis( l-hydroperoxy-
acids; was prepd by the action of iodine on 3,5 cyclohexyl)-peroxide in pyridine with p-nitro-
-dinitrobenzoylhy drazide in boiling alc soln. benzoyl chloride
Other props and methods of prepn are given in
the Refs. Its expl props were not detd Bis(benzoylperoxy)-dimethyl-hexane and
Re/s: l)Beil 9,415 2)T.Curtius & A. Riedel, Derivatives
JPraktChem 76,251(1907)& JCS 92 I, 970(1907) 2,5-Bis(benzoylperoxy)-2,5-dimethyl-hexane(cal-
B is(trinitroberzzoy l)-bya!razine, led Peroxybenzoic Acid, 1,1,4,4- Tetrametb yl-
[(02 N)3C~H2.C0.NH-]2; not found in Beil or in tetrametbylene Ester in CA Formula Index for
CA thru 1956 1949),
$H3 $H3
Bis(benzoyl)-peroxide. Same as Dibenzoylperoxirk CH3.$.CH2.CH2”$ .CH3
C6H5. C0.00 00.0C.C6H5
Bis(benzoylperoxy)-cyclohexane and Derivatives
mw 386.43, 0 24.84%; plate s(from methanoI), mP
1, l’-Bis(benzoylperoxy)-cyclohexane or 1, l-Di- 117°; expl in a flame; was prepd by treating 2!5
(benzoperoxy)-cyclobexane(called Peroxybenzoic -bis(hydroperoxy )-2, 5-dimethyl-hexane( qv) with
Acid, Cyclobexyliden e Ester in CA Formula Index benzoyl chloride in abs pyridine(Ref 2,p 141)
for 1950), CGHs.CO.OO-CgH, ~-00.C0.C6Hs; mw 2,5-Bis(P-nitrobenzoylperoxy)-2,5-dimethyl-hexane
356.36, 0 26.94%; rhmb prisms, mp 96°; expl when (called Peroxybenzoic Acid, p-Nitrol, l,4,4-tetra-
heated on a spatula in a fIame; was prepd by metbyltetrametby lene Ester in CA Formu1a Index
benzoylation of I-hydroxyperoxy cyclohexyl- 1 for 1949),
-hydroxycyclohexyl, C , ~H220~ (Compd VII of
$H~ ~H3
Ref 2,p 8) in pyridine with C6H5 .CO.C1 at 0°
CH3.$.CH2.CH2.~ .CH3 ;
(Ref 2,p 17)
02N.C6H4.C0.00. 00.OC.C H .N02
1, 1-Bis(p-nitrobenzoylperoxy)-cyclohexane or
mw 476.43, 0 38.58%; It yel Ifts, mp ;50t (dec);
1, 1-D ~p-nitrobenzopero xy)-cyclohexane(c ailed
can be prepd by treating 2,5-bis(hydroperoxy )-2,5
Peroxybenzoic Acid, p-Nitrocyclobexy lidene
-dimethyl-hexane with p-nitrobenzoyl chloride in
Ester in CA Formula Index for 1950),
abs pyridine. Its expl props were not investigated
02N.C6H4.C0.00-C6 H10-O0.C0.C6H4.N02;
Re/s: l)Beil- not found 2)R.Criegee & H.
mw 446.36, 0 35.85%, N 6.28%; It yel ndls(from
Dietrich,Ann 560, 141( 1948) & CA 43,6190(1949)
ale) or rhmb prisms(from AcOH), mp- expl at 120’?
was prepd by treating l-hydroxyperoxycyclohexyl
Bis(benzoylperoxy)-fluorene and Derivatives
-1-hydroxycyclohexyl in pyridine with p-nitro-
9,9’-Bis(benzoylperoxy)-fluorene or 9,9’-Di(benz-
benzoyl chloride at 0° (Ref 2,p 17)
peroxy)-fluorene (called Peroxybenzoic Acid,9
Re/s: l)Beil- not found 2)R.Criegee et aLAnn
-Fluorenylidene Ester in CA Formula Index for
565,8 & 17(1949); CA 44, 1917-16(1950)
1950),C6H5.C0.00\
3)Tobolsky & Mesrobian( 1954),178
C13H8; mw 470.41, 0 27.21%;
CGH5.C0.00’
Bis(benzoylperoxy)-dicyclohexylperoxide and
CO1 rhmb prisms(from methanol), mp 106°; expl
Derivatives
when heated on a spatula; was prepd by benzoyl-
1,1-Bis(benzoylperoxy )-dicyclobexylpemxide
ation of the mol aggregate C39Hz606(Compd
[called Peroxybenzoic Acid Diester with Bis(l
XVIII of Ref 2,pp 14 & 20), listed here as Bis(9
-bydroxycyclobexy l)-p emxide in CA Formula
-hydroperoxy)-fluorene+2 F luorenones(Adduct),
Index for 1950] ,
in pyridine with C6H5C0. CI at 0° (Ref 2,PP 14 &
C6H~.C0.00-C6H10.00.C6HI o-00. C0.C6H5;
20)
mw 470.50, 0 27.21%; prisms(from methanol), mp
9,9’-Bis(p-nitrobenzoylperoxy)-fluorene or 9, 9-Di-
9 2-3°; was prepd by benzoylation of bis( l-hydro-
(p-nitrobenzoperoxy )- fluorene (called Peroxybenz -
peroxycyclohexy l)-peroxide, C, *H2 206, pyridine
oic Acid, p-Nitrofluoreny lidene Ester in CA F or-
with C6H5.C0.C1 at OO(Ref 27PP 8 & 18)
mula Index for 1950),
Re/s: l) Beil- not found 2)R.Criegee et al, Ann
 B 136

02N.C6H4.C0.00 -triazene; 4- Diazoaminobipbenyl or 4, 4’-Dipbenyl-

\ diazoaminobenzene [called 1. 3-Bis-pdiphenylyl
C13H8; mw 528.41, 0 30.28%;
02N.C6H4.C0.00’ -triazen-( 1) in Ger],
It yel crYsts, mp 149-500; expl at higher temp; C6H5.C6H4.N:N.NH. C6H4.C6H5; mw 349.42, N
was prepd by reacting the above mol aggregate, 12.03%; yel plates or ndls(from warm ale), mp
C39H2606, in pyridine with p-nitrobenzoyl 147°; sol in benz, AcOH, alc & some other org
chloride at OO(Ref 2,p 21) SOIVS; insol in w & dil acids; can be prepd by
Re/s: l) Beil- not found 2)R.Criegee et al, Ann diazotizing p-aminobiphenyl, C6H~ .C6H4.NHZ
565,14 & 20-1(1949); CA 44, 1917(1950) (2 mols) in AcOH with Na nitrite(l mol) or by
9,9’~Bi s(benzoylperoxyfl uorenyl)~peroxide or9, 9‘ other methods(Ref 1)
Di(benzoperoxy)-9, 9’-/luorerze Peroxide [Dibenzo- Some of its salts are expl, for exampIe:
ate of 9,9’-Di(hydroperoxy )-9, 9’-fluorene P eroxide Perchlorate, (C6H5. C6H4)2N2.NH.C104; Ctysts,
designated in Ref 2,p 15 as “Dibenzoat des Per- expl on heating; was prepd by treating the tri-
oxyds XX”] [called Peroxyberzzoic Acid, Diester azene with perchloric acid and separating the
with Bis(9-bydro.ry-9-/luorenyl)-peroxide in CA resulting ppt. It was proposed for use in primary
Formula Index for 1950], and initiating compns(Ref 4)
C6H5.C0.00.C13H8 .00. C13HB.00.0C.C6H5; In addn to the above p-isomer, called by
mw 634.61, 0 20.17%; CO1 crysts(from benz), Fishbein(Ref 4) Diazo-4-aminodipb erryl Per-
mp 135 °(often with expln); can be prepd by chlorate, there was prepd the o-isomer, called
benzoylation of H.00.C ,3 H8.00.C, ~H8.00.H Diazo-2-aminodiph erzyl P ercblorate. This isomer
in pyridine with C6H5.C0.C1 at 0° also proved to be expl
Re/s: l)Beil- not found 2)R.Criegee et al, Ann Re/s: l)Beil 16,[356] 2)D.Vorlander,Ber 58,
565,21(1949) & CA 44, 1917(1950) 1914(1925) 3)F.Bell et al,JCS 1926,1246
4)M.S.Fishbein, VoyennayaKhimia 1933,N0 6,3
Bis(benzyl)-amine. Same as Dibenzylamine -8 & CA 29,7077( 1935)

Bis(benzylideneamino)-guanidine and Derivatives Bis(biphenylyl)-amine and Derivatives

Bis(berzzylidenearnino) -guanidirze(called N.N’-Bis Bis(p-bipbenyly l)-amine (called 4.4’-Diphenyl
-benzylidenamino-guanidin; O.d-Dibenqliden-di- -diphenylamin or Bis-p-diphenyly l-amin in Ger),
aminoguanidin; sym-N. N’-Bis-benzalamino-guani- [CGH5.C6H4-I,NH; mw 321.40, N 4.36%; lfts
din or Kohlensaure-imid-bis-benzalhydrazid in (from benz or xylol), mp 209°; other props and
Ger),~H.N:CH.C6H5 methods of prepn are given in Beil ~2,(546) &
$:NH ; mw 265.31, N 26.40%; yel [7551
NH.N:CH.C6H5 Bis(2,4,6-trinitro-p-biphenylyl)-amine or 2,4,6,2’, -
nlds(from ale), mp 176°; forms numerous tryst 4’,6’-Hexanitrobipbeny lyl-amine { called Bis 3.2’. -
salts; other props and methods of prepn are given 4’-trinitro-dipheny lyl.-(4aminin in Ger(Ref 1) and
in Beil 7,230,(127) & [173] 4,4’-Bis-op-dinitrophenyl-2,2’-dinitrodipheny1-
Bis(3-nitrobenzylideneamino)-guanidine[called amine by LeF6vre et al(Ref 2)],
N.N’-Bis-(3-r,itro-benzalamino}guanidin or (02 N)2C6H3.C6H3(N02 )-NH-C6H3(N02). CGH3-
Kohl ensaure-imid-bis-( 3-nitro-benzalhy in drazid) (N02)2, mw 591.40, N 16.58%; lt-yel ndls(from
Ger], (02N.C6H4.CH:N. NH-)2 C: NH; mw 355.31, phenol+ ale), mp 256-7°; diffc sol in common
N 27.60%; yel trysts, mp 240-242°; insol in com- SOIVS; was prepd by passing a current of dry
mon org SOIVS; was prepd by reacting the hydro- ammonia through a soln of 4’-bromo-2,4,3‘-tri-
bromide of N, N’-diamino-guanidine and m-nitro- nitrobiphenyl in boiling nitrobenzene. Its expl
benzaldehyde in ale. It forms @its, such $S the props were not detd
Hydrobromide, C, ~H, ~N704+HBr, yel pdr, gradu- Re/s: l)Beil 12,[764] 2) J. W. LeF?vre et al,JCS
ally reddens in the air and dec at 292°. Other 1927,2337 & CA 22,69(1928)
props are given in the Refs. The expl props of
the compd and its salts were not detd Bis(bromoanilino)-ethane and Derivatives
Re/s: l)Beil 7,(140) 2)A.Gaiter,Gazz 451,454 1, 2- Bis(bromoanilino)- etbune or 1, 2- Bis(bmmo-
(1915) & JCS 108 1,656(1915) pbenylamino)-etban e,
Br.CGH4.NH.CH2. CH2.NH.C6H4. Br. Two isomers
Bis(biphenyI)-triazene and Derivatives are described in Ref 2,pp 550 & 557. They may
I,III-Bis(p-biphenyl)-triazene; 1,3-Di(p-biphenyl) be considered as parent compds of the nitro

.— ———
 B 137

derivs, although not necessarily used for their isomer is known: 1, 3-Bis-N-(5’-bromo- 2’, 4’,6’
prepn -trz”nitm-nitranilino)-p ropane or 1, 3-Bis [N.(5’
-bromo-2’, 4’, 6’-trr”nitropb enyl)-nitramino l-prupane,
1, 2. Bis(bromo.nitroanilino} etbane Br(0.#)C6Hs-
NH.CH2 .CHZ .NH.C6H3(N02)?3r. Three isomers Br(02N)3C6H.N(N02 ). CH2.CIiz.CH2.N(N02).
are described in Ref 2,pp 551,558 & 864 C6H(N02)3Br; trysts, mp 117 ; SOI in acet, benz
toluene, glac AcOH & boiling ale; sparingly sol
l,2-Bis(bromo-dinitro-nitranilino)-ethane,
C14H8Br2N~012; in eth, petr eth, chlf & CC14. Was prepd by ni-
mw 640.10, N 17.50%. TWO
isomers are known: 1, 2- Bis. N-(2’- brorno-4’, 6‘ trating l,>bis( 5’-bromo-2’-nitroanilino propanene
-dinitronitranilino)-etbane, with absoI HN03 at 00. It is a powerful explosive
(Ref 2,pp 1011& 1014)
Br(02N)2C6H2.N(N02 ). CH2.CH2.N(N02). CGH2-
Re/s: l)Beil- not found 2)W .L .C .Veer,R ec 57,
(N02)2Br, CO1 trysts, mp 240; was prepd by ni-
trating 1,2-bis(2’-bromoaniIino)-ethane with absol 1009-12 & 1014( 1938)& CA 33, 1287(1939)
HN03 at OO(Ref 2,p 551). Its expI props were not
l,2-Bis(bromophenylamino)ethane. See Bis(bromo -
detd 1, 2-Bis-N-(4’-brorno~ 2’, 6 ‘-dinitro-nitrartilino)
aniline)-ethane
-ethane, pale-yel ndls, mp 205°; was prepd by ni-
trating 1,2-bis(4’-brom oanilino)-ethane or 1,2-bis-
l,3-Bis-N-(4’-bromophenylamino)-propane. See
(4’-bromo-2’-nitroanilinoethanene with absol HN03
at OO(Ref 2,p 557). Its expl props were not detd Bis(bromoanilino)-propane
l,2-Bis(bromo-trinitro-nitraniIino)-ethane,
2,2-Bis(t-butylperoxy)-butane,
Cf4H6Br2N10016; mw 730.10, N 19.18%; One
isomer is known: 1,2- Bis-N-(-5’-bromo.2’,4’,6 ‘.tri. CHzCH~
nitro-nitranilino)- etbane or 1, 2-Bis [N-(.5- brorno (CH3)3C-00-~-00-C(CH3 )3; mw 234.44, 027.3 1%;
-2’,4’, 6’-trinitropheny l)-nitramino]-e tbane, CH3
CO1 mobile liq, mp -0.8°, bp 26° at 0.2 mm and
Br(02N)9CeH.N(N02 ). CH2.CH2.N(N02).C5 H(N02)3-
50° at 2 mm; expl violently at 125-7°; d 0.889 at
Br, trysts, mp 187°; was prepd by nitrating 1,2
20°; Qc 1869 kcal/mol; n~ 1.415 at 20°; miscible
-bis-N-(5’-bromo-2’-nitroanilino)-ethane with absol
nitric acid at OO(Ref 2,p 863). Its exPI props with acet, octane or toluene; insol in q; no serious
were not detd toxicological hazard in normaI handling but high
Re/s: l)Beil- not found 2)A. E. Schouten,R ec 56, concns of vapor or Iiq in contact with skin should
550ff, 557ff, 863fY(1937) & CA 31,5335 & 7045(1937) be avoided; can be prepd by reacting t-butyl
hydroperoxide with methyl ethyl ketone in the
Bis(bromoanilino)-propane and Derivatives
presence of an acid catalyst(Refs 2 & 3)
This Iiq must not be distilled at atm press; in
1,3-B is(bromoarzilin e)-propane or 1, 3-Bis(bromo-
a coned state it can be decompd explosively a-
pbenylamino)-prop ane,
bove 85° and caution shotdd be exercized in this
Br.C6H4 .NH.CH2 .CH2 .CH2.NH.C6H4. Br. one
regard. This compd is sensitive to impact and
isomer is described in Ref 2,p 1009
burns rapidly when ignited(Ref 3)
I, 3-Bis(bromo-nitroanilino)-propane,
Wiles et al(Ref 4) have found 2,2-bis(t-buryl-
Br(OzN).CGH3.NH. CHz.CH2.CHzNH.C6H3(N02}
peroxy)butane to be useful as a polymerization
Br. one isomer is described in Ref 2,P 1009
sensitizer(or ‘catalyst”), Diesel fueI ignition
1, 3-Bis(bromo-dinitroanilino)-p ropan e,
accelerator and as a reagent of org syntheses
Br(02N)2.C6H2 .NH.CH2.CH2.CH2 .NH.C6H2(N02)~
Re/s: I)Beil- not found 2)F.H.Dickey,USP
Br. One isomer is described in Ref 2,p 1009
1, 3- Bis(bromo-dinitro-nitranilino)-propane, 2400041(1946) & USP 2455569(1948) 3)F.H.
Dickey et al,JACS 71 ,1432( 1949) & IEC 41,1673
Cl ~Hf oBr2N~01 z; mw 654.13, N 17.1270. One
(1949) 4)Q.T.Wiles et al, IEC 41 ,1679(1949)
isomer is known: 1, 3- Bis-N-(4’-b~mo-2’, 6 ‘-di-
5)Tobo1sky & Mesrobian( 1954), 180
nit ro-ni tranilino)-p rop an e,
Br(02N)2CeH2.N(N02) .CH2.CH2.CH2.N(N02)-
2,2- Bis(t-butylperoxy)-propane
C~H2(N02)2Br; cream-col scale s(from dil acet);
$Ha
mp 167°, expl at higher temp; was prepd by ni-
(CH3)3C-00-~-00-C(CHJz, mw 220.30, 0 29.05%;
trating 1, 3-bis(4’-bromoanilino) -propane or 1,3
CH3
-bis(4’-bromo-2’,6’-dinitraniline)oproPanene with
COI mobiie Iiq, n~ 1.4098. It was prepd by Dickey
absol HN03 at 0° (Ref 2,pp 1OO9-10 & 1014)
et al but not examined as an expl
l,3tBi s(bromaatrinitro* nitrani !ino)*propane,
Refq: l)Beil- not found 2)F.H.Dickey et al, JAC S
C1~HeBr2Nto016; mw 744.13, N 18.817%. One
 I

B 138

71, 1433(1949) Cl, mw 641.18, N 21.85 %.. One isomer is known:

1, 2- Bis-(j’-cblom-2’, 4’, 6’-trinitto-pitranilino)-etb-
Bis(caproyl)-peroxide. Same as Dicaproyl Per- ane or 1, 2-Bis[N-(5’-cbloro- 2’, 4’, 6’-trinitrophenyl)
oxide -nitramino]- ethane, pale yel trysts, tnp 170°, expl
at higher temp; was prepd by nitrating I,2-bis-
Bis(carboxamide)-acetylene. See Acetylenedi- (chloro-dinitro-nitraniline)-ethane with absol nitric
carboxamide, VO1 l,p A65-L acid at 0° (Ref 2,p 864)
Refs: l) Beil- not found 2)A. E. Schouten,Rec
Bis(carboxanilide)-acetylene or Di(N-phenyI- 56,547 ff,554ff, & 863~1937); CA 31,5335 &7045
carboxamide)-acetylene. (1937)
C6H5.NH.C0.CiC. C0.NH.C6H5 and its Hexa*
nitro Derivative, Bis(chloroanilino)-propane and Derivatives
(0,N)3C6H2.NH.C0 .CiC.C0.NH.C6HJN02 )3, 1, 3-Bis(cbloroanilino)-propane or 1, 3- Bis[N-(chlmo-
are described in conf 2nd Rept, ADL, SYnthesis Pbenyl)-amino]- propane,
HE’s(1951),142-3 & 153 CI.C6H4.NH.CH2. CH2. CH2.NH.CGH4.C1. One iso-
mer is described in Ref 2,p 1008
~,~’-Bis(carboxymethyl)aadipic Acid Tetraazide. 1,3-Bis(cbloro-nitroanilino~propme,
Same as Ethane-1,1,2,2, -tetraacetic Acid Tetra- C1(02N)C6H3.NH. CH2.CH2.CH2.NH.C6 H3(N02)CI.
azide One isomer is described in Ref 2,p 1010
1,3-Bis(chloro-dinitroanilino)-propane,
Bis(3-carboxypropionyl)-peroxide. See Bis(suc- Cl(02N)2C6H2.NH. CH2.CH2.CH2.NH. C6H2(N02~
cinyl)-peroxide Cl; mw 475.21, N 17.69%. One isomer is known:
1, 3-Bis(4’-cbloro- 2’, 6 ‘-dinitro-anilino)- propan e
Bis(chloroanilino)-thane and Derivatives or 1, 3. Bis[N-(4’-cbloro-2’, 6’-dinitropb enyl)-amino]
1,2-Bisfcbloroanilino)- etbane or l,2-Bis~-(cblotc- ‘Propane, yel trysts, mp 217°, exp! mildly; was
pb enyl)-amino]- etbane, prepd by boiling an alc soln of 2,6-dinitro-4-chloro
C1. C~H4.NH.CH2 .CH2.NH.C6H4.Cl. TWO isomers -anisole with l,3-diaminopropane. May be nitrated
are described in Ref 2,pp 547 & 554 to give more powerful expls described beIow(R ef
1, 2-Bisfcbloro-nitro anilino)-etban e or 1, 2-Bis[N 2,pp 1008 & 1013)
-(cbloronit?vpb enyl)-amino]-etb ane, 1,3-Bis(4’-chloro-2’,6’-dinitro-nitranilina)-propane
ci(02N).C~H3.NH. CH2.CH2.C6HJN02 )Cl. Three or 1, 3-Bis[N-(4’-cbloro-2’, 6’-dinitropbeny l)-nitra-
isomers are described in Ref 2,pp 549,5s5 & 863 mine]-propane,
l,2-Bis(chloro-dinitro-nitranilino)-ethane or 1,2 C1.@2N)2C6H2.N(N02) .CH2.CH2.CH2.N(N02)-
l Bi s[N*(chloro*d initrophenyl)*n itram ino]~ethane, C6H2(N02)2.CI; mw 565.21, N 19.82%; creqm COI
C@#)2C5H2.N(N02). CH2.CH2.N(N02),C6 H2- scaIes, mp 159-61°; expl violently; sol in acet,
(N09)aCl; mw 551.18, N 20.33%. Two isomers dioxane, hot benz, toIuene or chIfi insol in w,
are ~e~cribed in the literature: 1,2-Bis-N-(2’ alc, eth, petr eth or CC14; can be prepd by nitra.
-cbloro-4, 6*-dinitro-ni!rani lino)-etbane or 1,2 tion with abs nitric acid either l,3-bis(4’:chloro-
.Bis[N.(2'.cbloro-4 ',6' -dinitropbenyl)-nitramino] anilino)-propane or 1,3-bis(4’-chloro-2’, 6>-di-
-etbane, fine CO1 trysts, mp 238°; was prepd by nitroanilino)-propane( Ref 2,pp 1008 & 1014)
nitrating 1,2-bis((2’-chloro-4’-nitroanilinoethanene l,3-Bis(5’-chloro2’,4’,6’-trinitro-nitranilino)-pro-
1,2-bis(2’-chloro-4’ ,(?dinitroanilino)-ethane with pane or 1, 3- Bis[N-(5’-cblom-2’,4’, 6 ‘-trinitropbenyl)
abs nitric acid at RT (Ref 2,p 549). Its expl props -nitraminol.propane,
were not detd 1, 2- Bis-N-(4’-cblo~-2’, 6’-din.itro cL(02N)3CGH.N(N02 ). CH2.CH2.CH2.N~02) -
-nitranilino)-etbane Or 1,2-B is-[N-4’-chlom-2’, 6‘ CGH(N02)3.C1; mw 655.21, N 21.38%; trysts, mp
-dinitmpbenyl)-n itramino]- etharze, fine COI trysts, 100°; expl violently; sol in acet, benz, toluene,
m!? 201-30; was prepd by nitrating 1.,2-bis(4’-,chloro chlf, ACOH & dioxane; SI sol in ale, eth & petr
-2’-nitroanilino)-ethane or 1,2-bis(4’-ch10ro-2 ?,6~ eth; insol in w; was prepd by nitration with abs
-dinitroanilino)-eth ane with abs nitric acid(Ref 2, nitric acid of 1,3-bis(5 ‘-chloro-2’-nitroanilino)
-propane(Ref 2,pp 1010-11 & 1014)
P 554. Its expl props were not detd
R e/y: l) Beil- not found 2)W.L.C.Veer,Rec 57,
l,2-Bis(chloro-trinitro-nitranilino)-ethane or 1,2
1008,1010-11 & 1013-14(1938) & CA 33,128743
-Bis[N-(’chloro- trirzitropb enyl)-nitraminol. ethane,
(1939)
C1(02N)3C6H.N(N02 ). CH2.CH2.N(N02).C6 H(NO)3-

. —._._
 B 139

Bis(chloromethyl)thallium Chloride, (ClCH=)9- 0- 0-

TICI; very unstable expl solid; was prepd b~~. + ~t—CHK ~CH-~<
Ya Yakubovich & V. A. Ginsburg, DoklAkadN 73, NiN.C c–c, C.k~N or
957(1950) & CA 45,2857(1951) “CH= CH’ CH= CH’
~ q
1,2-Bis N-(5’-chlorophenyl)-amino-ethane. See ,C—CH< CH-C, + .
Bis(chloroanilino) -ethane Ii: Ii:c, ./c–c+ C.M:N; mw 238.20,
CH=CH \CH=CH’
1,2-Bis[N(4’-chlorophenyl)-amino]-propane. See
Bis(chloroanilino)-propane l,2-Bis(diazo)-ethane, N2CH.CHN2; mw 82.07,
N 68.28%; was prepd by adding NaOH or KOH to
1,1‘.Bis(o-chlorophenyl)-5,5’-azotetrazole or Azo a cold, well-stirred abs aIc soln of 1, 2-bis-nitro-
-di[s.(o-cbloropb enyl)- l-(a-tetrazole)] (callkd A zo soureidoethane, (CH2)Z [N(NO) -CONHZ]2. The
-1. 1‘-o-chlorophenyl-5. 5’-tetrazol in Ger), product was not isolated but allowed to react in
~:N.~ N:N ~.N:~; mw387.20, situ with an alc or eth soln of an acid or phenol
N= C.(CGH4.C1) (CLH4Ce).C=N Re/s: l)Beil- not found 2)C.M.Samour & J.P.
N 36. 18%, OB to C02 -132.2%; CO1 trysts, mp- Mason,JACS 76,442(1954) & CA 49,3018(1955)
expl ca 122° or on impact; sol in cold coned
H2S04, from which it may be pptd with w; in sol Bis(diazo)-heptane, CH2 (CH2CH2CHN2 )2; m w
in w; nearly insol in common org SOIVS; can be 152.20, N 36.82%; orn-yel oil, very unstable; was
prepd by treating 1, l-dichloroamino-5-( o-chloro- prepd by nitrosation of
phenyl)wz -tetrazole with aq KI soln followed by CH2(CH2.CH2 .CH2 .NHCOOCZHS )2, followed by
addn of an aq soln of a thiosulfate treatment with cold KOH
Refs: l)Beil- not found 2)R.StoI16 et al, JPrakt Refs: l)Beil- not found 2)T.Lieser & G. Beck,
Chem 138,2 & 10-11(1933) & CA 27,4798(1933) ChemBer 83, 141(1950)& CA 44,7233(1950)
3)F.R.Benson,ChemR evs 41, 16(1947)
1,6-Bis(diazo)-hexane, N2CH(CH2 )4 CHN2; mw
1,4-Bis(diazo)-butane,N2CH.CH2.CH2.CHN2; 138.17, N 40.55%; deep orn oil, dec spontaneous-
mw 110.12, N 50.88%; yel, very unstable oil; ly at 10° with evolution of N; cannot be distd in
was prepd by treating an erhereal soln of the bis- a high vacuum; was prepd from
nitrosoureid, [CH2 .cH2.N(NO)CONH2]2, with aq Hz NCH2(CH2)4CH2NH2 as a starting material,
KOH at 00 and allowing it to react with benzoic the HC1 salt of which, after adjustment with
acid, p-nitrobenzoic acid, phenol, /3-naphthol or NaOH to a pH 9, was converted by reaction with
catechol(Refs 2 & 3). Samour & Mason(Ref 4) aIso aq KCNO to H2NCONH(CH2)4NHCONH2 and on
prepd bis(diazo)-butane by this and other methods nitrosation by reaction with NaN02 and treatment
but they did not isolate the product, allowing it to with well-cooled KOH below 0°, gave the desired
react with carboxylic acids, aldehydes, acetone, product(Refs 3 & 4). Kirst(Ref 2) had earlier ob-
phenol or ethyl acetoacetate served the definite tanning effect of this compd
Refs: I) Beil- not found 2)H. Lettr6,Naturwissem on limed animal hides, but he did nor describe
schaften 36,57( 1949) & CA 44,3892(1950) 3)T. its prepn. Buckley & Ray(Ref 5) described and
Lieser & G. Beck, Chamber 83,140(1950) & CA 44> patented the use of bis(diazo)-hexane with ortho-
7233(1950) 4)C.M.Samour & J. P. Mason,JACS 76, borate esters at 0° to obt branched chain p araf-
441( 1954) & CA 49,3018( 1955) fins of high mw, and tough, flexible rubbery fiIms
(Ref 7). Samour & Mason(Ref 6) reported cross
4,4’aBis(diazo)-3,3’-dioxy-biphenyl[called4.4’ -linked products resulted from treating poly -
-Bis-diazo-3.3’-dioxy-diphenyl or Diphenyldichinon acrylic acid or polymethacrylic acid with an alc
.(3,4,3’,4’}bis-diazid-( 4.4’) in Gerl, soln of bis(diazo)-hexane. Expl props of the
SEE FORMULA NEXT COLUMN compd were not investigated
N 23.52%; orn ndls, mp expl violently on heating; ,Re/s: l)Beil- not found 2)W.Kirst, Melliand
was prepd by diazotization of 4,4’ -diamino-3,3’ Textilber 28, 169(1947) & CA 42,8480(1948)
.dihydroxy-biphenyl or its disulfate in acid soln 3)H. Lettr6 & U. Bros6,Naturwissenschaften 36,
with NaN02 57(1949) & CA 44,3892(1950) 4) T. Lieser & G.
17efs: l)Beil 16, [292] 2)G.N.Burkhardt & H. Beck, Chamber 83, 138(1950) & CA 44,7232(1950)
Vood,JCS 1929,149,151’ 5)G.D. Buckley & N. H. Ray,JCS 1952,3701 & CA
 I

B 140

47,8006(1953); BritP 701203(1953) & CA 48,9106 2,2’-diaminoazobenzene-4,4’-disulfenic acid with

(1954 );and USP 2671767 (19 S4)&CA 48,7342 ale, HCI and excess of ethyl nitrite
(1954) 6)C.M.Samour &J. P. Mason, J.4CS? 6,444 Refs: l)Beil 16,619 2)T.Zincke & A. Kuchen-
(1954 )& CA 49,3019(1955) 7)N.H.Ray,USP becker,Ann 330,21( 1904)
2670333(1954); BritP 709395 (1954 )& CA 49,4007 Bisdiazotetrazolylhydrazide. See [N’ ,I@ -B is(a
(1955) -tettazolyl-5)1 -hexazadiene, VO1 l,P 260-R, under
Aminotetrazole
l,5-Bis(diazo)-pentane, N2CH(CH2)3CHN2; mw
124.15, N 45.13%; yel, very unstable oil; was 1,2-Bis[N-(4’,6’-dibromo-2’-nitrophenyl)-nitramino]
prepcl by niwosation of CH2(CH2CHNHCONH2)2 ethane, Br2(N02)C6H2 .N(N02).CH2~CH2 .N(N02) -
to give CH2[CH2CIiN(NO)CONH2]2 which on CH2 .CH2.N(N02)CGH2 (N02)Dr2; mw 707.91, N
treatment with KOH gave the desired product. 11.87%; pale yel ndls(from rlil rlioxane), mp 207°,
Its expl props were not investigated expl mildly on heating to higher temp; sol in di-
Re/s: l)Beil- not found 2)H. Lettr6 & U. Bros6, oxane, boiling acet, benz to!uene or chlf; insol
Naturwissenscha ften 36,57(1949) & CA 44,3892 in w, ale, eth, petr eth or C.C14; was prepd by
(1950) 3)T.Lieser & G. Beck. ChemBer 83,140 nitration of 1,2-b is(4’,6 ‘-dibromo-2’-nitrophenyl-
(1950) & CA 44,7233(1950) amino)-ethane, previously obtd by reacting 1,3
-dibromo-4, 5-dinitrobenzene with ethylene di-
Bis(p-diazophenol)-dichromate, amine in alc soln
(HO.C H4.N2)ZCr207; N 12.2%, trysts, mp- expl Refs: l)Beil- not found 2)’T.L.C .Veer, Rec
ca 134? when dry and pure; was prepd by diazo- 57,1012 & 1014(1938)
tization of p-amin~phenol followed by addn of a 1,3-Bis[N-(4’,6’-dibromo-2’-nitrophenyl)-nitramino]
bichromate. It is fairly st abIe, but I ess so than -propane, Br2(N02)C6H2 .N(N02 ). CH2.CH2 .CH2 -
the chromate obtd from p-phenyIenediamine( Ref N(N02)CGH2(N02) Br2;mw 721.94, N 11.64%; yel
2,pp 4-5). The same author prepd chromates of crysts(from dil dioxane), mp 199°, expl mildly on
diazonium and nitrodiazonium derivatives of heating to higher temp; sol in dioxane, boiling benz,
aniline, bromoaniline, chloroaniline, benzidine, acet, chlf or toluene; insol in w, ale, erh, petr eth
p-phenylenediamine, etc and found them more or or CC14; was obtd on nitration of the 1,3-bis nitro-
less expl when dry phenylamino deriv previously prepd
Re/s: l)Beil- not found 2)R.h4eldokJcs 87 I, Re/s: Same as above
4-5(1905) l,2-Bis[N-(4',6'-dichloro-2'-nitrophenyl)-nitramino]
-ethane, Cl ~(N02)C6H2.N(NOz ).CH2 .CH2 .N(NOz)C6H2-
l,3-Bis(diazo)-propane,,N2CH.CH2.CHN2; mw (N02)C12; mw 530.08, N 15.86%; pale yel c~sts
96.09, N 58.3 1%; very unstable oil; was prepd by (from dil dioxane), mp 196°, expl mildly on heat-
treating 1 mol of CH2 (CH2 .NH.CONH2)2 in 2 ing to higher temp; sol in dioxane, boiIing acet,
mols C2H5N02 with HC1, neutralizing tk mixt benz, toluene or chlf; insol in w, ale, eth or pem
with Na2C03 and washing the oil with w to give eth; was prepd by nitration of 1,2-bis(4’,6’-di-
CH2[C ~N(NO)COzC2H5]2 which, with KOH in chloro-2’-nitrophenylamino)-ethane, previously
NaCL-ice mixt, gave the product. Its expI props obt d by reacting 1,3-dichloro-4,5 -dinitrobenzene
were not investigated with ethylene diamine
Re/s: l)Beil- not found 2)T.Lieser & G. Beck, Re/s: l)Beil- not found 2)W.L. C. Veer,Rec 57,
ChemBer 83,140(1950) & CA 44,7233(1950) 1012 & 1014( 1938)
l,3-Bis[N-(4',6'-dichloro2'-nitrophenyl)-nitramino]
Bis(2-diazo-sulfenyl-N,S-oxy)-azobenzene, -propane, Clz (N02 )C5H2 .N(N02 )~CH2 IC’H2 .CH2 .N{N02)-
[called 2. 2’-Bis diazo-azobenzol-disulfonsaure C6H2(N02 )C12 ; mw 544.11, N 15.4570; almost COI
-(4.4’) in Beil(Ref 1) and Diazoverbindurrg des crysts(fro~ al~+ acet) contg 0.5 C2H50H; mp
O-diamidoazobenzol-p-disulfonsiiure by Zincke 149°, expl mildly on heating to higher temp; sol
& Kuchenbecker(Ref 2)] in acer, benz, toluene, chlf or CC14; S1 sol in
O—--—N:N N!N —–-— -0 ale; insol in eth or. petr eth; was prepd by ni-
I CH-:
02S. C4
~&CH\ I tration of 1,3-bis(4’,6’-dichloro-2
-propane, previously
-nitrophenylamino)
obtd by heating an alc soln
‘C-N: N-C\cH=cH>c.so2+ 2H20 ;
‘CH=CH’ of 1,3-dichloro-4,5 -dinitrobenzene and 1,3-d iamin~
mw 430.38, N 19.53%; yel pdr, mp expl violently propane
on heating; sol in alkalies, giving a red soln; Refs: l) Beil- not found 2) W. L. C. Veer,Rec 57,
nearly insol in w or aIc; was prepd by heating 1014 -15( I938)
 B 141

Bis(diethyl) Lead Styphnate, Basic, Bis(dimethylamino)-triphenylmethane and

Derivatives
(02N)3C6H[OPb(CHz. CH3)20H]2; mw 871.77, N
Bis(dirnetbylamino)-tripbenylmethane or Tetra-
4.82%; yel trysts, mp expl ca 229°; was prepd
by Burrows et al(Ref 2) by reacting diethyl lead rnetbyl-diamino- tripbenylmetbane, C23 H2 ~N2.
dichloride and diammonium styphnate at RT. It Three isomers are described in Beil 13,273-5,
detonates with a firing current of 0..3l-O.36amps (89) & [1351
(VS 0.40-o.47amp for lead styphnate) and was Mononitro-bis(dim ethylamino)-tripbeny lmetbane,
proposed for use as an ignition compn in elec C23H25N302. Three isomers are described in
blasting caps Beil 13,278-80 & [136]
Refs: l) Beil- not found 2)L. A. Burrows et al, Dinitro-bis(dimethy lamino)-tripbeny lmetbane,
C23H24N404. Two isomers are described in
USP 2105635(1938)& CA 32,2357(1938)
Beil 13,280 & [137]
Tri-, Tetra- and Perztanitro Derivatives, were
Bis(dihydroxypropyl)-oxamide and Derivatives
not found in Beil or in CA thru 1956
N, N’-Bis(2, 3-dibydroxypropy l)-o.vamide; N, N’-D i-
(f3:y-dibydroxypropyl)- oxarnide, Hexanitros.4,4’.bis(dimethylamino).triphenyl.
methane, (CH3)2N. (02 N)3C1 ~Ha(N02)3 .N(CH3)2;
[HO. CH,CH(OH).CH,.NHCO-],; mw 236.22, N
11.86%; was obtd by the reactions: mw 600.45, N 18.66%; golden-yel ndls(from
AcOH), mp zoOO (dec); fairly SOI in alc, acet &
Hcl -~ NaOH
glycerin - chlorohydrin --—-—- - ACOH especially on warming; was prepd by treat-
ing 4,4’-bis(dimethy lamino)-tripheny lmethane,
glyceride ~-~.3. + H2 N.CH2 .CH(OH). CHZ OH (CH3 )2N.C#4 . H.CGH4 .N(CH3)2, with fuming
s .H=
‘.c? ‘522s2-s~-+ [HO,CH, “CH(OH)”CH, 0NH”c~12
nitric acid(d 1.4)~R~fs 1,2 & 3). It expl sharply
On nitration it yields the following expl deriv(Ref 2): on sudden heating(Re f 3)
Ref.s: l)Beil 13,280-1 2)0. Fischer,Ber 1 ~,950
N.N’-Bis(2,3-dihydroxypropyl)-oxamide Tetra (1878) 3)Ibid,Ann 206,128(1881)
nitrate or N, N’. Di(/3, y-dibydroxypropy l)-oxamide
Tetranitrate listed in CA Coil Formula Index Bis(1,1-dimethyl-2-propynyl) Peroxide. See Vol 1,
(1920-1946),p 281 as C*H1 ~N601 ~ or p A66-R
$0. NH. CH2.CH(HON02).CH, (HON0,); mW
C0.NH.CH2.CH(HON02 ). CH2(HONOZ) l’,2’-Bis(2,2-dinitroalkyl)-amines of general
420.26, N 20.00; listed in BIatt as a compd of formula [R(N02)2C.CH212NH were prepd recently
empirical formula CeH, ~N601 ~ or in Sweden by treating 2,2-dinitroalkyl- l-ethanol
~ONHCH2CH(ON02 )CH2(ON02); mw 416.22, N with 2,2-dinitroalkyl- l-amine: R(02N)2C.CH2 .OH
CONHCH2CH(ON02 )CH2(ON02 ) + H2N.CH2.C(N02)R = [R(02N)C.CH212NH+ H20.
20.19%, OB to C02 -30.8%; mp 142.5°, exPI on Some of these compds may be suitable as in-
heating to 178°; was prepd by nitrating the gredients of expl and propellant compositions
parent compd with a mixt of HN03 and H.#04 Refs: 1 )Beil- not found 2) F. R. Schenck & G .A.
below 10°. This compd is a powerful expl of ~~letterholn,swedp 148217( 1954); BritP 729469
high stability. Its props resemble those of N ,N’ (1955); USP 2731460(1956)& CA 50, 1893,7125
-dinitro-N,N’-dimethy l-oxamide, (1956)
02 N(CH3 )N.C0.C0.N(CH3 )N02
Blatt(Ref 3) lists the foIlowing expl props as N,N’-[Bis-(2,2.dinitroalkyl)-hydrazines] of general
reported in Ref 2: Impact Sensitivity, 2kg wt, formula, R(02N)2C.CH2.HN. NH. CH2C(N02)R
positive at 60cm vs 60-80cm for TNT; Lead were prepd recently in Sweden by the action of
~lock E.vpansion, 325cc vs 266cc for TNT at d 1 mol hydrazine on 2 mols of 2,2-dinitroalkyl-l
1.1; Thermal Stability, no decompn at 70° for -ethanol:
200hrs; Velocity o/ Detonation ,4030 m/see in 2R(OZN)2C.CH20H + H2N.NH2 = 2H20 + [R(02N)2
paper tubes at d 0.62 C. CH2.NH-]2
Refs: l) Beil- not found 2)T.Domanski & J. Some of these compds ate suitable as ingredients
Skudrzyk,RoczChem ,19,2127(1939) & CA 34, of expl and propellant compositions
4056(1940) 3)Blatt,0SR~ 2~1~1944) Re/s: l)Beil- not found 2) F. R. Schenck & G.A.
T’etterholn,SwedP 148217(1954); SritP 729469
Bis(1,3-dimethylamino)-benzene. Same as N~,- (1955); USP 2731469(1956)& CA 50,1893 &
N’,N’-Tetramethyl-m-phenylenediamine 7125(1956)
 I

B 142

Bis(dinitrobenzoyl)-peroxi de. See D i(dinitro- -Bis(@-hydroxyethyl) -sulfamide, described under

benzo yl)-peroxide under Dibenzoylperoxi de N, N’-Di(ethylol)-sulf amide

2,2’-Bis(3,5-dinitro-4-hydroxyphenyl)-propane. Bis(ethylamine), Same as Diethylamine

See under Bis(hydroxypheny l)-propane
Bis(ethyl)-ethylenediamine. Same as Diethyl-
Bis(3,5-dinitro-4-hydroxyphenyl)-sulfone. See ethyl enediamine
under Bis(hydroxypheny l)-sulfone
Bis(ethylhexyl)-phthalate,
Bis(2,4-dinitrophenyl)- disulfide. See 2,4,2’,4’ C, H,[COO.CH(C,H, ). CH,. CH2. CH,. CH,]2 ; mw
-Tetranitrodipheny l-disulfide under Diphenyldi- 390.54; CO1 liq, d 0.984 at 21°, n~ 1.48i91 at
sulfide 25°, Q; 3298.2 kcal/mol and Q~ 252.6kcal/mol;
miscible with ale, eth, acet and many other org
1,3’.Bis(l,3-dinitroxy-2-nitramino-propane)-2’,4’,6' solvents. It was suggested as a possible compo-
-trinitrobenzene. See Vol l,p A252-L nent of propellants
Refs: l)Beil- nor found 2)P.Tavernier & M.
l,3-Bis(2,3-dinitroxy-1-nitraminopropane)-2’,4’,6’ Lamouroux,Mp 37,203 & 206(1955)
-trinitrobenzene. See Vol l,p A2>2-R
Bis(ethyl)-hydrazine. Same as Diethylhydrazine
Bis(diphenylcarbamide)-Ethylenediamine Complex.
See under Diphenylcarbamide Complexes Suitable Bis(ethylnitrosamino)-azoxybenzene,
as Stabilizers and Gelatinizes in Smokeless C2H5.N(NO)-C6H4 .N20.C6H4.N(NO) .C2H5;
Propellants 342.35, N 24.55%; ye! ndls(from ale), rnp 171°;
was obtd on treating ethyl-( 4-nitrosophenyl)-
Bis-diphenylurea (called Bis diphenylur6e in Fr -nitrosamine in alc solrr with Na amalgam. Its
and N.N ‘-Bis diphenylaminoformyl-h ydrazin in expl props were not investigated
Ger), (C6H5)2N.C0.NH.NH. C0.N(C6H5)Z; mw Re/s: I)Beil 16,655 2)0. Fischer, Ann 286,158
422.47, N 13.26%; CO1 trysts, mp 215-217°, giving (1895)
a tvh vapor; Q: 3214kcal/mol; Q: - 14.6kcal/mol;
sol in acet; S1 sol in cold w, alc or chlfi was 1,3-Bis(ethyltriazeno)-benzene or 3, 3’-m-Phenyl-
prepd by reacting 1 mol of hydrazine hydrate ene-bis( I-ethyltriazene),
with 2 mols of diphenyIcarbamic acid chloride H5C#IN.N:N.C6H4. N: N. NH.C2H5; mw 220.28,
(Refs 1 & 2). This compd was claimed by Tavemier N 38.16%; yel ctysts(from ale), mP 104°, exPl on
& Lamouroux(Ref 3) as one of a number of org sudden heating; easily SOI in acet, eth or chlf;
derivs suitable for incorporation in smokeless diffc sol in ligroin or tofuene; decomp violently
propellants by ACOH. Was prepd by the action of ethylmag-
Refs: l)Beil ]2,(258) 2) B. Toschi,Gazz 44,. nesium bromide on 1,3-diazobenze.ne in ether
445(1914) & JCS 106 1,740(1914) 3)P.Tavernier Re/s: l)Beil 16, [356] 2)H.Kleinfeller, JPrakt-
& M. Lamouroux,MP 38,73 & 83(1956) & CA 51, Chem 119,65(1928) & CA 22,2566(1928)
14403(1957)
N,N’-Bis(5-ethyl-s-triazol-3-yl)formamidine or
l,3-Bis(ß-ethanolamino)-benzene. Same as 1,3 3,3’-Bis(5-ethyl-lH-l,2,4-triazolyl)-formamidine,
-Bis(fi-hydroxy ethyl amino )-benzene, described H5C2.~-N=$-N:CH. NH-$= N-$. C2H5; mw 234.27,
under 1,3-Di(~-ethylol amino)-benzene N —NH HN—N
N 47.84%; wh rhombs, mp 263°; was prepd by
N.N’-Bis(ß-ethanol)-ethylenediamine. Same as boiling for 2 l-m, 2 mols of 3-amino-5 -ethyl-s
1,2-Bis(@-hydroxy ethylamino)-ethane, described -triazole with an excess(over 1 mol) of ethyl-
under 1, 2-Di(~-ethyloI)-ethy lehediamine orthoformate, followed by cooling. This high
-nitrogen compd was patented as a stabilizer
N.N'-Bis(ß-ethanol)-oxamide. Same as N~’-Bis(~ for photographic emulsions. Its expl props were
-hydroxyethyI)-oxamide, described under N~’ not investigated
-Di(ethylol)-oxamide Re/s: l) Beil- not found 2) J. D. Kendall &
H. G. Suggate,USI? 2534914(1950) & CA 4%
N.N’-Bis(ß-ethanol)-sulfamide. Same as N m‘ 2350(1951) 3)Ibid,USP 2588538(1952) &
 143

CA 46,4405-6(1952) Bishydrazicarbonyl or Diurea. See Note under 4

-Aminourazole, Vol l,p A272-L
9,9’-Bis(fluorenyl)-diperoxide{called Dispiro
[fluorene-9,-?’-s- tetroxane-6’, 9“-fIuorene] in CA 3,6-Bis(hydrazide)-l,2-dihydro-l,2,4,5,tetrazine
Formula Index for 1950 and aDimeres FIuorenon- [called the Dihydrazid of l.2-Dihydro-l.2 .4.5
peroxyd” in Ref 2] -tetrazin-dicarbonsaute-(3.6) in Ger],
~ #oo\ ,,NH-NH,
,C13He; mw 392.39, 0 16.31%; It yel H2N.NHOCO-c~N_N# ‘C. C0.NH.NH2; mw
‘3 8’00
prisms(from dioxane or tetrahydrofurane), mp 200.17, N 55.99%; yel crysts(from w), mp ca
203° with decompn; expl miIdIy when heated in 265-275° (dec); sol in 800p boiling W; was obtd
a tube; was obtd on treating the adduct 9,9’-bis- in an impure state by heating the diethylester of
(hydroperoxy)-fluorene+ 2Fluorenones, C9 ~H26C)6, l,2-dihydro-l,2,4, 5-tetrazine-3,6-dic arboxylic
with N/10 Pb acetate soln in AcOH(Ref 2,p 21) acid with an excess of hydrazine hydrate or
Re/s: l) Beil- not found 2)R.Criegee et aI,Ann anhyd hydrazine
565,15 & 21(1949); CA 44,1918(1950) Its Hydrochloride, C4HaN~02+2HCl, small
violet-red trysts, exploded violently on heating
3,6-Bis(fluorenylidenehydro)-sym-tetrazine or Re/s: l)Beil 26,570 2)T.Curtius & E. Rimele,
Bis(dipbenylen em ethyl en e)- dib ydm tetrazirze Ber 41,3113-3114(1908) & CA 3,67(1909)
(called 3.6-Difluorenyliden-3 .6-dihydro-l.2.4.5
-tetrazin in Ger), Bis(hydrazino)-adinitrobenzene and Derivatives
l,3-Bis(hydrazino)-4,6-dinitrobenzene called
~~>C:C<N=N\C:Cx~’H4 ; rzw 408.44, N [4.6-Dinitro-l.3-dihydrazino-benzol or 4.6-Dinitro
N.N~ “C6H4 -phenylendihydrazin-( 1.3) in Ger],
46
13.72%; grn prisms with metallic Iuster(from benz), (H2N.NH)2C~H2(N02 )2; mw 228.17, N 36.84%;
mp expl mildly ca 240°; sol in benz; SI sol in brn ndls(from nitrobenz), mp 3 IOO(decompg with
eth acet; nearly insol in alc or eth; can be prepd a f 1a sh); other props and methods of prepn are
by shaking at RT 3,6-bis(9-chloro or bromo-$1 given in Ref 1, This compd may be considered
-fluorenyl)-l,2,4,5 -tetrazine, as the parent compd of the following umstable
derivs:
1, 3-Bis(benzylideneby drazirzo)-4, 6-dinitrobenzenq
(C6H5.CH:N,HN)2 C6H2(N02)2; mw 404.38, N
benz~lic suspension of Hg. Oth~r ~rops & methocb 20.78%; red lfts(from nitrobenz), mp 302-304°
of prepn are given in the Refs (dec); mod sol in boiling nitrobenz; insol in alc
Re/s: l)Beil 26,(120) 2) R. Stol16 et al,Ber 46, or AcOH; was prepd by heating 1,3-bis(hydrazino)
235(1913) 3)J.Lifschitz,Ber 48,415-16(1915) -4,6-dinitrobenzene with benzaldehydg in aq alc
HC1 or nitrobenzene(Refs 1 & 2,p 681)
Bis(hexahydrobenzoyl)-peroxide or Bis(cyclo- 1, 3- Bis(dipbenylmetby lenebydrazino)-4, 6-din itro -
hexanecarbonyl)-peroxide(caIled di-hexahydro- benzene, [(C6H~ )2 C:N.NH]2CGH2 (N02 )2; mw
benzoyl-peroxyd by Fichter & Siegrist), 556.56, N 15. 10%; yel ndls(from nitrobenz), mp
p q becomes brn ca 280°, dec 305°; mod sol in
$H2-CH2 -CH- C_O.O_c- H_CH2_qH2; mw nitrobenz; almost insol in alc or AcOH; was
CH2-CH2-CH2 : H2-CH2-CH2 prepd by heating 1, +bis(h ydrazino)-4,6-d initro-
254.32, 025. 17%; oil evolving C02 at RT; benzene with benzophenone in aq alc HC1, follow
large quants can expl without apparent reason; ed by addn of a Na acetate salt(Refs 1 & 2 ,pp
was obtd when the anhydride of cyclohexane 671, 682) ~
carboxylic acid in abs eth was shaken with 93% 1, 3- Bis(z “1opropylidenebydrazino) -4, 6-dinitrobenz-
of the calcd quant of finely powd B a02 .8H20. ene, [( H3C)2C:N.NH12C6 Hz(N02)2; mw 308.30,
Rapid concn of the eth soln in vacuo yielded N 27.26%; orn ndls(from AcOH or et acet), mp
the desired product 234-235°(dec); was prepd by heating acetone
Re/s: l)Beil- not found 2) F. Fichter & W. with l,3-bis(hydrazino)-4,6-dinitrobenzene in aq
Siegrist,Helv 15, 1304(1932) & CA 27,279(1933) alc HCI(Refs 1 & 2,p 681)
3)Tobolsky & Mesrobian( 1954), 179 1, 3- Bis(metbyletzebydrazino)-4, 6-d~nitrobenzene,
(H2C:N.NH)2C5H2 (N02)2; mw 252.19, N 33.33%;
 B 144

yel ndls(from alc or nitrobenz), mp 247°(dec); prism s(from dil .AcOH) or ndls(from hot w), expl
sol in boiling nitrobenz; diffc sol in boiling when heated in a flame; was prepd by tre sting
AcoH; almost insol in ale; was prepd by treating cyclohexanone with an ethereal soln of H202
1, 3-bis(hydrazino)-4,6-dinitrobenzene in boiling in the coId(Ref 2,p 17 & Ref 3)
aIc HCI with formaldehyde, followed by addn of Its Acetone Compound { called “Isopropyliden
Na acetate(Refs 1 & 2,p 680) -di-cyclohexyliden-triperoxyd” in G er(?lef 2 ,p 11)
1, 3- Bis(~-pb enylbydrazino)-4, 6-din itrobenzene, and 17, 17- DimetbyI-7,8, 15, 16, 18, 19-he xoxadispiro
(C6H5.NH.HN)2C6 H2(N02)2; mw 380.36, N 22.10%; -[5. 2.5. 5]-rzonadecarze in CA Formula Index for
orn-red crysts(from acet+alc), mp 211-212°(dec); 19501, H10$6—O0 mW 302.36,
—–$6HIO;
sol in acet or chlf; diffc sol in alc or eth; was 00–C(CH3 )2 –00
ob.td, together with >-chloro-2 ,4-din itrohydra zo- O 31.75%; CO1 crysts(from methanol), mp 64°;
benzene, by the action of phenylhydrazine on s expl by heat or friction; was obtd by aHowing a
-chloro- 1,2 ,4-trinitrobenzene (Refs 1 & 3) mixt of 1, I’-bis(hydroperoxy cyclohexyl)-peroxide,
Re/s: l)Beil 15,[266] 2)W.Borsche,Ber ~,671, anhyd acetone and anhyd Cu sulfate to stand for
680-682(1921) & JCS 120 1,461(1921) 3)M.Giua, 14 days(Ref 2,p 18)
Gazz 51,312(1921) & JCS ]20 1,551(1921) Re/.s: 1 )Beil- not found 2) R. Criegee et al, Ann
565,8 & 17-18(1949); CA 44,1917(1950) 3)Tobol-
sky & hjesrobian( 1954), 179

Bis(hydroonthranol) and Derivatives Bis(hydroperoxy)-dicyclohexyl Peroxide. Same

Bis(hydroantbrarzo~), C 28 H 22 0 z> mw 390.46, 0 as 1, l‘-Bis(hydroperoxy cyclohexyI)-peroxide
8. 19%; although not described in the literature,
may be considered as the parent compd of its
nitro and nitrate derivs, although they were not
prepd from it
Bis(nitrohydroanthranol) or 9,9’-Dinitro-9,9‘-di- 2,5-Bis(hydroperoxy-2,5-dimethyl)-hexane[ caIled
bydroxy - 10, 10’-dihydroanthracene[ caIled 10.10’ (1, 1,4,4- Tetramethyltetrametby lene)-dibydrv-
-Dinitro- 10. 10’-dioxy-9. 10.9’. IO’-tetrahydro-di- peroxide in CA Formula Index]
anthranyl-(9.9’) in Ger],
CHa CH.
ON 2 \/64\ CH ,C6H4, ,N02 H3C–&~CH2.CH2—~ .EH3; mw 178.22, 0
c CH.HC c ; mw bOH HOO
HO’ \C6H4’ \C6H4’ IO H
35.91%; prisms(from w or benz), mp 104-5°; expl
480.46, N 5.83%; yel ndls, mp sublimes at 120°, in flame but not by friction; was prepd by treat-
dec 267 -268°; burns explosively at higher temps ing anhyd tetramethyl-1,4-butanediol with 7 5%
or in contact with a flame; SI SOI in ale, eth or hydrogen peroxide(Ref 2,p 141)
benz; dec in hot dil NaOH; was prepd by adding Its Acetone Compound(called 3,3,6,6,9,9 -Hexa-
HN03 dropwise to a mixt of pure anthracene in methyl- 1,2,4, 5-tetroxonane in CA 5th Decennial
ACOH and acet at 7-8° during 2 hrs, and heating Formula Index),(CH3)2~–CH 2.CH2— $(CH~)2;
to 50-55° after standing at RT for two days(R efs 00-C(CHa)2–00
1&3) mw 218.29, 0 29.32%; crysts(from methanol), mp
Its Dirzitrate, C28H22N401 o, mp 290°, resem- 42-3°; expl at higher temp; was obtd by allowing
bling bis(nitrohydroanthranol) in all other props, a mixt of 2, 5-bis(hydroperoxide)- 2,5-dim ethyl-
was obtd when the product of nitration was heat- hexane, anhyd acetone and anhyd Cu sulfate to
ed to 50-55° after 3 hrs standing at RT(Refs 2 & stand for 14 days(Ref 3,p 18)
3) Benzolation of 2, 5-bis(hydroperoxy-2,5 -dim ethyl)
Re@: l)Beil 7,[797] 2)Beil 5,[572] 3)J.5. -hexane yielded the Dibenzoate, C22H2 ~06, fine
Turski & A. Berlandstein,RoczChem 7,457(1927) pltlts(from MeOH), mp 117°, exploding when heat-
& CA 22,3159(1928) ed in a flame. Also, there was prepd the Di-p
-nitrobenzoate, C22H24N2010, It yel Ifts, mp
1,l’-Bis(hydroperoxycyclohexyl)-peroxide or 1, 1‘
150°, exploding on heating in a flare e(llef 2)
-Bis(hydroperoxy)-dicyclohexyl Peroxide, Re/s: l) Beil- not found 2) R. Criegee & H.Dietrich,
00, Ann 560,141( 1948) & CA @,6190(1949) 3)R.
HI ~CG’ $6H10; mw 262.30, 0 36.60%; CO1 Criegee et al, Ann 565,18( 1949) & CA 44,1917
6 OH HOO (1950)

.—
 B 145

9,9’-Bis(hydroperoxy)-fluorene+2Fluorenones V. Villiger,Ber 33,2484(1900) 4) F. Fichter & E.

(Adduct) (formerly misnamed “Fluorenon-oxoxyd’ Uhl,Helv 3,37(1920) & JCS 118 1,234(1920)
in Ger) (listed as ‘Fluorenone Compound with
9 5)C.S.Marvel & V. Nichols, JOC 6,296(1941) &
- Fluorenylidenediby drop eroxide” in CA F OMI da CA 35,3997(1941) 6)Tobolsky & Mesrobian
Index for 1950), (1954),171
00.H
C H’ +2C ,3H~O; mw 590.60, 0 16.25%, Bis(1-hydroxycyclohexyl)-peroxide or 1, 1‘-D i-
‘ 3 *\oo.H bydroxy-dicyclohex yl- 1, 1‘-peroxide (called D i
yel crysts(from hot benz or toluene), mp 108-108.50; -cyclohexanon-peroxyhydrat by Stoll & Scherrer),
expl when heated on a spatula or brou#rt in ‘con- ?H (3H
tact with coned sulfuric acid. It was first prepd ~H2–CH2–$-0.0-~ — CH2–<H2; mw 230.30,
by ‘1’ittig & Pieper on treating fluorenone with an CHZ-CH2-CH2 CH2 -CH –CH2
ethereal soIn of HZ 02 in the presence of P205 O 27.79%; COI ndls, mp 68-70%, expl violently on
(Ref 2). They claimed that the resulting peroxide attempting to purify it by vac distn; was prepd by
had the formula C, ~ H~ 02 and called it “Fluoran treating cyclohexanone with HZ02. When treated
-peroxyd”. Criegee et al(Ref 3) claimed that the with dil H2S04 it, gave an intermediate product
compd prepd by W & P was not fluorenone peroxide OH
but the adcluct shown in this item C6HI< , called, l- bydroxycyclobexy lbydro-
When heated at 85-90° and 0.01 mm Hg, this \ OOH
complex yielded fluorene and the adduct,C ~gH2 ~- peroxide in Ref 5,p 171 and with coned H$04 it
07(1 mole fluorenone and 1 mole H. OO.C1 ~H8.- gave cyclohexanone monop eroxide, C H -? (Ref
6 lo-o
OO.C1 ~H~.00H), It yel trysts, mp 134-5°, expl 2,pp 143-4 & 149)
in flame(Ref 3,p 21) Re/s: 1 )Beil-not found 2)M.Stoll & W.Scherter,
Benzolation of 9,9- bis(hydroxyfluoreny l)-per- Helv 13,142-4 & 146-9(1930); CA 24,2732(1930)
oxide, called ‘t Peroxyd YX” by Criegee, 3)N.A.Milas et al, JACS61,2431(1939) 4)R.
HOO.C ,3 H8.00.C1 ~H8.00H),gave the Perory- Criegee et al, Ann 565,7( 1949) & CA 44,1917(1950)
benzoic Acid Diester, 5)Tobolsky & Mesrobian(1954), 171 & 179 6)N.
C6H5.C00.C13H*.00 .C1%H8.CO0.C6H5, CO1 Brown et al, JACS ~~, 1759(1955) 7)L. Homer &
crysts(from benz), mp 135 , frequently detonating W. Jurgeleitt,Ann 591, 150(1955) & CA 50,2498
(Ref 3,p 21) ( 1956)
Re/s: l)Beil- not found 2)G.Wittig & G.P ieper,
Ber 73,296-7(1940) 3)R.Criegee et al, Ann 565, Bis(hydroxyethoxy)-benzene and Derivatives
14 & 20-1(1949) & CA 44,1917(1950) 1,3-Bis(2-bydroxy etboxy)-benzene or Di-fl-hydrvxy.
ethyl-m-pbenylene Ether [called Resorcin-bis-(~
Bis(a.hydroxybenzyl).peroxide{called Bis-[a-oxy -oxy-athylather) in Ger], C6H4(OCH2 .CH2 .OH)Z;
-benzyl]-peroxyd; a .a ‘-Dioxy-dibenzy lperoxyd or mw 198.21, 0 32.29%; CO1 trysts, mp 81°; sol in
Dibenzalperoxydhy drat in Ger], alc or methylethyl ketone; insol in eth, benz or
C6H3.CH(OH).0.0 .CH(OH).C6H5; mw 246.25, Iigroin; was prepd by treating res orcinol, in Na
0 25.99%; crysts(from benz), mp 60-62°; insol ethylate soln, with ethylene chlorhydrin(Refs 1&
in w, cold eth or petr eth; was prepd by treating 2). This may be considered the parent compd of
benzaldehyde with HZ02 be!ow 30 °(Ref 2). See its nitrated derivs
also Refs 1,4,5 & 6 Re/s: l)Beil 6, [816] 2)R. E. Rindfusz et al,
Either in the solid state or when treated with JACS 42, 163(1920)
Na carbonate, it is dissociated into benzaldehyde 1,3- Bis(2-bydroxyetbo xy~mononitrobenzene,
and HZC)2; cold acetic anhydride converts it into Cl OH, ~N06, not found in Beil or in CA thru
acetic peroxide, acetic acid and benzaldehyde 1956
(Refs 1 & 2). On adding benzaldehyde to a dil l,3.Bis(2.hydroxyethoxy).4,6.dinitrobenzene
alc soln of H202 and H2S04, Baeyer & Villiger [listed in CA Coil Formula Index,p 424 & 5th
(Ref 3) obtd ~ p;oduct, - O-O\cH c H Decennial Formula Index,p 578F, as 2,2’-(4, 6
C6 H5 .CH< “65 -Dinitro-m-pbeny lenedioxy)-dietbunol and in
o–o’ Abstract as 4, 6-Dinitroresorcirrol- bis(or di)(2
which they called diberzzaldebydebip eroxide, the -bydroxyetbyl)-ether] [called 4,6-Dinitrophenyl
inner anhydride of the compd obtd by Nef(Ref 2) - 1,3-di((3-hydroxy ethyl ether by Blanksrna & Fohr
Re/s: l)Beil 7,21o & [161] 2)J.U.Nef,Ann 298, and 4,6-Dinitro-resorcin-di-oxathyl-ather in Ger
292(1897) & JCS 74 I,11O( 1898) 3) A. Baeyer &
 B 146

by Ruggli & Straub],(02N)2C6 kf2(OCH2.CH2.0H)2j Bis(ß-hydroxyethyl)-oxamide. See Di(ethylol)

mw 288.21, N 9.72%; col lfts(from w), mp 135°; -oxamide
readily sol in ale, AcOH or boiling w; mod sol
in eth acet; diffc sol in eth, benz or chlfi was Bis(ß-hydroxyethyl)-peroxide. See Di(ethylol)
prepd by adding monosodium glycolate to a mixt peroxide
of 1,3-dichloro-4,6-dinitrobenzene and glycol(Ref
2&3) Bis(hydroxyethyl)-piperazine and D erivatives
Its ester, 1, 3- Bis(2-bydroxyetboxy )-4, 6-din itro- N, N’-Bis(2-hydroxy etbyl)-pip erazine or N, N’-Di(2
berzzerze Dirzitrate,(02N)2C H (OCH2.CH2.0N02)2; -ethylol)-pip erazine [called N. N’-Bis(/3-oxy-athyl)
CO1 ndls(from ale), mp 116$, $ec 170°, ignites at -piperazin in Ger],
275°; readily sol in ale, benz, chlf or acet; SI sol .CH. -CH.
in w, eth or light petroleum; was obtd by dissolv- H0.CH2.CH2.N{ ‘ ‘\ N.cH2.cH2.0H; mw
ing the compd in HN03 and pptg the product by CH, -CH>’
pouring on ice(Ref 3) 174.24, N 16.08%; t~trg p~ramid crysts(from ale),
l,3-Bis(2-hydroxyethoxy)-2,4,6-trinitrobenzene mp 134-1350; very sol in w; sol in chlf; diffc SOI
Dinitrate [listed in CA Coil Formula Index,p in other org SOIVS; was prepd by heating piper-
545F, as 2,2Z(294* 6-t~nitro-m-Phe nylenedioxy)-di- azine with ethylene chlorohydrin at 105°. This
ethanol Dinitrate and in Abstract as 2,4, 6- Tn”- compd forms numerous salts, such as Hydro-
nitm- 1, 3-bi~ 2-by droxy ethoxy)-benzene Dinitrate] chloride, Hydrobromide, Nitrate. The Auric
[called 2,4,6-Trinitrophenyl-1,3-di(~-hydto~- Chloride or Gold Tricb~oride,
ethyl ether) Dinitrate by Blanksma & Fohr]; C*HI ~N202+ 2HCl+2AuCl~ , forms lt yel ndls(from
(02 N)3C6H(OCH2.CH2 .0 N0,)2; mw 423.3 I, N dil HC1), mp 205-207° (dec); and the Picrate, yel
16.55%; CO1 ndls of bitter taste(from ale), mp ndls(from ale), mp 245-246° (dec)
75°, dec 175°, ignites and expl 265°; readily Re/s: l)Beil 23,10 2)F.L.Pyman,JCS 9311,1802
sol in acet or benz; mod sol in ale, eth or chlf; ( 1908)
v S1 sol in w or light petroleum; was obtd on N,N’-Bis(2-nitroxyethyl)-piperazine Dinitrate,
nitration of 1,3-bis(2-hydroxy ethoxy)-4,6-din itro- + CH2 –CH
benzene dinitrate by dissolving it in anhyd HN03 02 N0.CH2.CH2.N’ 2\~.CH2.CH2.0.N02-
& coned H2S04 and pptg the product by pouring fi\cH, -CH<ti
the soln on ice(Ref 3). On boiling this compd +2NOj; mw 390.27, N 21. 53Z; crysts(from MeOH),
with caustic soda in aq soln, there was obtained mp 129°; was prepd by nitrating N,N ‘-bis(2-hydroxy -
2,4,6- Trinitroresorcinol ethyl )-piperazine with 98% HN03 below 10° and
Re/s: l) Beil- not found 2)P.Ruggli & O. Straub, pptg the product by pouring on ice. This compel
Helv 21,1099(1938) & CA 33,1327(1939) 3)J.J. and related compds were investigated in the
Blanksma & P. G. Fohr,Rec 65,816-818(1946) & search for semi-expl plasticizers for flashless
CA 41,2704(1947) propellant powders
Re/s: l) Beil- not found 2) A. T. Blomquist,0SRD
Bis(hydroxyethyl)-amine. See Di(ethylol}amine 5155( 1945),P 129
and Derivatives
N,N’-Bis(hydroxyethyl)-propyleneamine. See N ,N’
Bis(ß-hydroxyethylamino)-benzene. See 1,3-Di((? -Di(ethylol)-propy leneamine
-ethylolamine)-ben zene
N,N’-Bis(hydroxyethyl)-propylenedinitramine. See
Bis(ß-hydroxyethylamino)-ethane. See 1,2-Di(/3 N, N’-Di(ethyIol)-propy lenedinitramine under N ,N’
-ethyl ol)-ethylene diamine -Di(ethylol)-propy leneamine

Bis(2-hydroxyethyl)-ammonium Nitrate, See Di- Bis(ß-hydroxyethyl)-sulfamide. See Di(ethylol)

(ethylol)-ammonium Nitrate -sulfam ide

N,N’-Bis(2-hydroxyethyl)-N,N'-dinitroxamide, Bis(hydroxylamino)-azide. See Vol l,p A525-L

designated as NENO, is described under Di(ethyl-
ol)-oxamide N,N’-Bis((ß-hydroxymethyl)-amine. See Di(methyl-
ol)-amine
Bis(2-hydroxyethyl)-ethylenediamine. See N ,N’
-Di(2-ethylol)-ethy lenediamine
 B 147
.

N,N’-Bis(ß-hydroxymethyl)-benzene. See D i- JCS 100 1,656(1911)], (H0)2C26H ,00(NOZ)6; mw

(methylol)-benzene 648.40, N 12.96%; crysts(from acet+MeOH>
readily sol in ale; insol in eth or Iigroin; was
2,6-Bis(hydroxymethyl)-2,6-dinitrol,7-heptanediol prepd by nitration of the tetranitro d eriv(R efs
Tetranitrate. See 2,6-DimethyloI-2 ,6-dinitro- 1,7 1 & 2). Its expl props were not investigated
-heptanediol Tetranitrate Re fs: l)Beil 8,(678) 2)w’.W.Schwa~in et al,
ZhRusFiz-KhimObshch 43, 570(19 11) & JCS
2,5-Bis(hydroxymethyl)-2,5-dinitro-l,6-hexanediol
100 1,655-6(1911)
Tetranitrate. See 2, 5-Dimethylol-2, 5-diflitro-I,6
-hexanediol Tetranitrate 4[Bis(p-hydroxyphenyl)-methylene]-2,5-cyclo-
hexadiene-l-one. See under Aurine; Vol l,p
Bis(hydroxymethylether)-peroxide. See Di(methyl- A508-R
ol)-di(oxymethyl ene)-peroxide
Bis(hydroxyphenyl)-propane and Derivatives
Bis(hydroxymethyl)-ethylenediamine. See Di- Bis(hydroxypbeny l)-propane, C, ~H, ~ 02; m w
(methylol)-ethylenediamine 228.28, 0 14.02%. Two isomers are described in
the literature: CH3 .CH2 .CH(CGH4 .0 H)2[c alled
Bis[(hydroxymethyl)-2-methoxy]-ethane. See Di- 1. l(or a.a)-Bis-(4-oxyphenyl )-propan in Ger(Ref
(methylol)-methoxy-eth ane l)]; and (CH3 )2C(C6H4 .0H)2 [called 2.2(or (?.9 )
-Bis-(4-oxy-pheny l)-propan in Ger(Ref 2)]. Their
Bis(hydroxymethyl)-methyl-aminomethane. See props and methods of prepn are given in the Refs.
under Aminomethylpropsne-diols; VOI l,p A232-R Qc at 25° 1868kcal/mol & Qf 88.2kcal/mol for
2,2-Bis(4-hydroxyphenyI)-propane(Ref 3)
Bis(hydroxymethyl)-methane. See Di(methylol) Re/s: l)Beil 6,1011 &[977] 2)Beil 6,1~01,(493)
-methyl-methane & [978] 3)W.N.Hubbard et al, JACS ~0,3259
(1948)
4,4-Bis(hydroxymethyl)-oxazolidone. See 4 ,4-D i- 2, 2- Bis(x-rzitro-4- bydro.xyphenyl)- propane [called
(methyloI)-oxazolidone /3.~-Bis-(x-nitro-4-oxy-phenyl)-propan in Ger],
(CH3)2C[02N.C6H3 .0H]2; mw 318.28, N 8.80%;
Bis(hydroxymethyl)-peroxide. See Di(methylol) golden yel crystsj mp 133°; forms a dk-red Na
-peroxide salt; other props and method of prepn are given
in Beil 6,1012
Bis(hydroxyphenyl)-anthranone and Derivatives 2,2-Bis(3,5-dinitro-4-hydroxyphenyl)-propane
10, 10- Bis(4-bydro.vyp beayl)-9- anthranone[called [called @.~-Bis-(x,x-dinitro-4oxy-phenyl)-propan
10.1 0-Bis(4-oxy-pheny I)-anthron-(9) or 1O-OXO in Ger],(CH3 )2 C[(02N)2C6H2.0H] ; mw 408.28,
- 9.9-B is(4-oxy-phenyl) -9. 10-dihydro-anthracen in N 13.72%; lt-yel trysts, mp 233-43, expI on heat-
Ger], ,C6H4, ing to higher temps; readily sol in hot w and
Oc C(C6H4.0H)2; mw 378.40, 0 alkali; diffc sol in ale, benz or eth; can be prepd
‘CeH4~ by nitration of the acetate of 2,2-bis(4-hydroxy -
12.68%; ndls(from dil ale), mp 308-309°; other phenyl)-propane( Refs 1 & 2) or by heating equi-
props and method of prepn are given in Beil S, molar amts of phenol and acetone in excess
373,(677) H2S04 followed by nitration (Refs 3,4 & 5)
10, 10-Bis(4-bydro.vyp benyl)- x, x-dinitro-9-antbra- Analogous compds have been prepd by con-
none, (HO)2C26H140(N02 )2; mw 468.40, N 5.98% densing a variety of aldehydes and ketones with
grn-yel Ifts, rnp 236° ; other props and method of phenols, the parent compds forming salts which
prepn are given in Beil 8,(677) were claimed to be suitable as ignition agents
10, 10-Bis(4-bydroxyphenyl-. v, X,x, .wtetranitro-9 (Refs 3,4 & 5)
-antlm-anone, (HO)2C26H1 *O(N02)4; mw 558.40, Its Lead Salt of 2 ,2’-bis(3, 5-dinitro-4-hydroxy -
N 10.03%; lemon-yel ndls(from acet+MeOH), mp phenyl)-propane has been patented(Ref 4) as an
278°; readily sol in ale, AcOH, chlf or acet; less ingredient, in admixture with KC103 , or zirco-
sol in eth; was prepd by nitration of the dinirro nium and NS, of igniticm compositions; and as be-
deriv ing suitable for use in Electric Blasting Initiators
Re/: Beil 8,(677) i?e/s: l)Beil 6,1012 2)T.Sz6ki,CR 190411,1737
10,10-Bis(4-hydroxyphenyl)-x,x,x,x,x,x-hexanitro 3)DuPont,BritP 431945(1935) & CA 30,109(1936)
-9-anthranone[called Hexanitrophenolanthrone in 4)W.F.Filbert & W. E. Lawson,USP 2118501(1938)
 I

B 148,

&CA 32,5630(1938) 5)BIatt,0SRD 2014(1944) coned H2S04 with SI foaming; gives a It brn-red
color with ferric chloride; dec on heating with
dil alkali; was prepd by treating the hydrazine
salt of oxaldilydrazide dioxime [C2H8N602+NZH4,
Bis(hydroxyphenyl)-sulfone and Derivatives
Beil 2,56o] with NaN02 in dil HCI, under cooling.
Bis(4-hydroxypheny l)-sul/one(called SulfonyIdi-
This compd detonates violently on impact or
pbenol in CA 5th Decennial Formula Index)[cal-
friction(Refs 1 & 2). It is of lower power and
led Bi s(4-oxy-phenyl) -sulfon; 4.4 ‘-~ ioxy-diphenyl -
brisance than PA and considered too sensitive
sulfon or 4.4’ -Dioxy-sulfobenzid in Ger],
for use as a high expl(~efs 3 & 4)
H0.C6H4.S02 .C6HQ.0H; mw 252.29, 0 25.37%;
Refs: l)Beil 26,6o8 2)H.Wieland,Ber 42,4205
ndls(from w), mp 238 -239°; forms salts; other
(1909); JCS 96 1,885(1909) & CA 4,33 O(191O)
props and methods of prepn are given in Beil 6,
3)A.H.Blatt & F. C. W’hitmore,OSRD 1085( 1942),p4
861 & [853]
4)Blatt,0SRD 2014(1944)
Bis(3-nitro-4-bydro.ryp benyl)-sulfone,
02 S[02N.C6H3.0H]2; mw 340.27, N 8.23%; yel BiS(a-hydroxy-ß,ß,ß-trichloroethyl)-peroxide
-wh pltlts(from ale), mp 236°; forms numerous or Bis(2, 2,2- trzcbloro- l-bydroxyetbyl)-p eroxide
salts; other props and methods of prepn are given (called Dichloralperoxydhydrat in Ger),
in ?3eil 6,865-6 C13C.CH(OH).0.0 .CH(OH).CC13; mw 328.81, 0
Bis(x-nitro-4-hydroxy phenyl)-suI/one( called x-Di- 19.47%; lfts or pltlts(from benz or chlf), ndls + 1
nitro-x-dioxy-dipheny lsulfon in Ger), yel plates mol eth(from eth, dec on exposure to light, mp
(from .4cOH), mp 229-230°, burns without ex- 122 o(dec); readily sol in ale, eth or AcOH; less
ploding; other props and method of prepn are SOI in benz or chlf; was obtd by treating chloral
given in Beil 6, [858] ether with an ethereal soln of H202 or with
Bis(3,5.dinitro.4.hydroxyphenyl).sulfone[called
Care’s reagent(persulfuric acid, H0.S02.0.0H)
4, 4’-Sulfonyl- bis(2, 6-dinitropbenol) in CA 5th (Refs 1,2 & 3)
Decennial Formula Index] [called Bis(3.5-dinitro Minkoff(Ref 4) detd the infra-red absorption
-4-oxy-phenyl)-sulfon or 3.5.3’. 5’-Tetranitro-4.4’ spectra of this compd and of a number of other
-dioxy-diphenyl sulfon in Ger], org peroxides
0SS[(02N)2C6H2.0H]2; mw 430.27, N 13.02%; Re/s: l)Beil i ,623 2) A. Baeyer & V. Villager,
very bittertasting straw yel ndls(from boiling w), Ber 33, 2481( 1900) & JCS 78 1,627(1900)
mp 257-258 °(Ref 4); insol in most org SOIVS; can 3) Tobolsky & Mesrobian(1954),171 4)G. J.
be prepd by nitrating either bis(3-nitro-4-h ydroxy - Minkoff,PrRoySoc 224A,184(1954) & CA 49,
phenyl)-sulfone or bis(4-hydroxypheny l)-sulfone 57(1955)
and by hydrolyzing bis(3, 5-din itro-4-c hlorophenyl)
-sulfone(Refs 1 & 2). It forms salts which can be Bisimidazoline. See Biimidazoline
used in ignition compositions(Ref 3)
Refs: l)Beil 6,867 2)F.UIImann & J .Korselt, Bis(^2-2-imidazolinyl). See Biimidazoline
Ber 4~,647(1907) 3)Blatt,0SRD 2014(1944)
4)G.Machek et al,klontsh 80,9(1949) & CA 43, Bis(methoxymethyl)-peroxide. See Di(methoxy-
6994( 1949) methyl)-peroxide

Bis(hydroxypropyl)-amine. Same as Di(propylol) Bis(methylamino)-anthraquinone and Derivatives

-amine Bis(rnethylarnino)- antbraquinone, C ,GH ,4N202.
Two isomers are described in the literature:
N,N’.Bis(ß.hydroxypropyl)-ethylenediamine. Same
1,5-Bis(rnetbylarnino)-antbraquinone(called Di-
as N, N’-Di(propylol)-ethy lenediamine
methyldiaminoanthraquinone by Schmidt), (Ref
2) and 1, 8- Bis(metbylamino) -antbraquinone
5,5’-Bis(l-hydroxytetrazole) or >, 5’-Bi( l-hydmxy-
(Ref 3,p 739) (Compare with Diaminodimethyl
tetrczzole) {called l.l’-Dioxy-[di-tetrazoly l-(5.5’)] -anthraquinone)
in Ger], ~–N(OH)-C–C –N(OH)-N; mw 170.10, Dinitro-bis(metby lamino)-antbraguinone,C1 ~H1 ~-
N fi fJ----- .;
N406. According to Ref 3,p 737, nitration of
N 65.88%; CO1 ndls(from w) or Ifts(from ale); 1,5-isomer to give 4,8- dinitro- 1, .5-bis(metbyl-
color gradually becomes yel to brn on storage; amino)- antbraquinone was patented in Germany
mp expl violently on heating to 176°; sol in alc (Ger P 156759). This patent was not at our dis-
or boiling w; inso~ in other SOIVS; dissolves in posal
 B 149

Tetranitro-bis(methylamino)-anthraquinone, used, the mixt takes fire. Other props and

CIGHIONGOIO; mw 446+29) N 18.83%. One methods of prepn are given in the Refs. GaI-
isomer is described in the literature: 1, 5-Bis- inowski & Urba~ski(Ref 3) prepd the compd by
(rnethylamino)-te tranitro-antbruqu inone, treating Autamine Hydrochloride with I-12S04 +
NH.CH~ HN03 at 60-70°
02N.$= CH-C-CO-#= C.N02 Re/s: l)Beil 14,100 2) P.van Romburgh,Rec 6,
02N.C= C= 8-CO-C-CH= (!.N02 251 & 367(1887); JCS 54 II, 1079 & 1196(1888)
AH.CH3 3)S.Galinowski & T. Urba~ki, JCS 1948,2169
-70(1948) & CA 43,2982(1949)
(positions of nitro groups are uncertain); red
-violet crysts(from amyl alc + ethanol), mp220°
(dec); exploded violently when heated in quan- Bis(methylamino)-diphenylmethane
tity; was prepd by nitration of l,5-bis(methyl- and Derivatives
amino) -anthraquinone with nitric acid(d 1.4) at 4,4’ -Bis(metbylamin o)-dipbenylmetbane,
a temp below 30°(Ref 3,p 738) Cl ~HteN2 is described in Beil 13,239& [111]
Re/s: l)Beil- not found 2)R.E.Schmidt,Ber Mono-, Di- and Trinitroden’vatives- not found in
37,70( 1904) 3)R.H.HaH & D. H. Hey,JCS 1948, Beil
737-9 & CA 42,8183(1948) 4, 4’-Bis(metbylamino)-3, 5,3’, 5’-tetranitrodi-
pbenylmetharze, CH2[C6H2(N02)2. NH.CH ]
Bis(methylamino)-benzene. See under Dimethyl- mw 406.31, N 20.69%; orn ctysts, mp 2508( ~ec);
phenylenediamine and Derivatives sol in boiling et acet, acet, AcOH or chlf; diffc
sol in ale, petr eth or benz; other props and
Bis(methylamino)-benzil and Derivatives method of prepn are giv~n in Beil 13,246
4,4* -Bis(metbylamino). benzil, C ,6H ,6N202. 4,4'-Bis(methylnitramino)-3,5,3',5'-tetranitrodi*
Although not found in the literature, it may be phenylmethane, CH2[C6~(N02)2.N(N02 ). CH3]~
considered as a parent compd of the following mw 496.31, N 22.58%; yel trysts, mp darkens
nitro deriv: at 210°, dec ca 217-220°; mod sol in warm acet;
4,4'-Bis(methylamino)-3,5,3',5'-tetranitrobenzil, almost insol in boiling ale, eth, petr eth, chlf
CH3.NH.CGH2(N02)2 .C0.C0.CeH2(N02 )2NHCH~ ; or CS2; was prepd by treating an acetic acid
mw 448.30, N 18.7570; brn-grey powd(from nitro- soln of 4,4’ -bis(dimethylamino) -diphenylmethane
benz), mp 223°; was prepd by heating 3,5,3’,5’- with nitric acid of d 1.5. When boiled with phenol,
-tetranitro-4 ,4’-dimethoxybe nzil with an alcoholic this compd gives the above 4,4’-bis(methyl-
soln of methylamine. Its expl props were not detd amino)-tetranitro deriv. When oxidized with
Refs: l)Beil 14, [98] 2)J van Alphen,Rec 48, chromic anhydride(Cr03 ) in AcOH, it is con-
1119(1929) & CA 24,844(1930) verted to 4,4’-bis(methylnitramino)-3, 5,3’,5’
-tetranitrobenzophenone. Other props are given
Bis(methylamino)-benzophenone and Derivatives in Refs. Its expl props were not investigated
4, 4’-Bis(metbylamino)- benzopbenone, Re/s: l)Beil 13,246 2)P.van Romburgh,Rec
Cl ~H ,~N20 is described in Beil 14, 89 7,228(1888) & JCS 56 1,146(1889)
4, 4’-Bis(metbylamino)-3, 3’.dinitro-benzopbenon6
C,5 H14N405 is described in Beil 14,100 Bis(methylaminomethyl)-methylamine and
4, 4’-Bis(metbylamino)-3, 5,3’, 5’-tetranitrobenzo- Derivatives
pbenone,[CH3NH. C6H2(N02)2]2CO; mw 420.29, Bis(metbylaminom ethyl)- metbylamine,
N 20.00%; gold, shiny crysts(from boiling phenol), ~. CH2-N-CH2.~H ; mw 117.19, N 35 .85%; not
mp ca 225° (dec); diffc sol in common SOIVS; CH, ~H, CH,
other props and method of prepn are given in found in Beil; may be considered the parent compd
Beil 14,100 of its dinitramino deriv, described below:
4,4’-Bis(methlnitramino)-3,5,3’,5’-tetranitro- f3is(methylnitram inomethyl)~methy lamine,
benzophenone,[02N. N(CH3).C6H2(N02 )2]2CO; 02N.q.CH~-N — CH2.~.N02; mw 207.19,
mw 510.29, N 21.96%; It yel trysts, mp dec ca CH3 ?H~ CH~
215°; almost insol in common SOIVS; S1 SOI in N 33.80%; nearly CO1 crysts(from chlf), mp
acet or AcOH; was prepd by treating 4,4’-bis- 64. 5-65.5; when heated in a test tube, it melted
(dimethylamino)-benzophenone (Michler’s Ketone) and decompd; dropped on a red-hot plate, it ig-
in the cold with nitric acid of sp gr 1.48 and nited with a bright flame(Ref 2); was prepd by
boiling the mixt. If nitric acid of sp gr 1.53 is adding methylnitramine to an aq soln of methyl-
 B 150

amine and formaldehyde cooled to 5°(Ref 3) Bis(l-methyl.1.ethl-2-propynyl)-peroxide.

Re/s: l)Beil- not found 2)R.McGill,OSRD 787 See Vol l,p A66-R
(1942) 3) J. R. Johnson,0SRD 915(1942),pp 2&
30 l,3-Bis(3-methyl-4-nitro-5-pyrazolyl)-triazene,
HN.N:C(CHa).C(NO, ):d.N:N.NHC:C(NO, ).-
Bis(methylamino)-toluene and Derivatives C(CH= ): N. fJ-H; mw ~95.23, N 42.72%; yei
Bis(metbylamino)- toluene, C ~ H , ~N2. One isomer tryst ~, mp 151-2°, dec violently with evolution
3, 4-Bis(methylarnino)- toluene,CH3C6H3(NH. CH~ of gas; dissolves in dil NaOH giving an intense
is described in Beil 13,153 violet-red soln, which on acidification reppt
Bis(methylamino)-dinitrotoluene, the compd unchanged; insof in aq alk carbonates;
CHa.C6H(N02)2(NH. CHa)z; mw 240.22, N 23.33%. was prepd by treating 3-meth yl-4-nitro- 5- amino
Two isomers are described in the literature: -pyrazole in HC1 at 0° with NsN02 and Na
2,4-B is(metbylamino)-3, S-din itrotoluene, acetate for several hours. This compd forms
exists in two forms, red Ifts, mp 168-170°, on an orn-red Silver salt; reacts with diazomethane
crystn from acet converts to yel form, and yel to form the trimethyl deriv, a yel compd, mp
ndls, mp 110°, changes to red form at 140°(Ref 163-4° (dec); and with phenylisocyanate,
1); and 3, 5-B is(metbyIamino)-2, 4-dinitrotoluen~ PhNCO, to form a compd, golden-yel trysts,,
It red trysts, mp 140°(Ref 2). Other props and tutning maroon-red at 150°, dec at 240°.
methods of prepn are given in the Refs The parent compd in alc soln was found to be
Re/s: l)Beil 13,142 & (42) 2)Beil 13,165 fairly good indicator for titration of acids but
less precise in titrating alkalies
2,4.Bis(methylnitramino).3,5.dinitroto!uene, Re/s: l)Beil- not found 2) C. Musante,Gazz
CH3.CGH(N02)2[N(N02 )-CH3]2 mw 330.22, N 76,297(1946) & CA 41,7298(1947)
25.45%; trysts, mp 169°; sol in boiling ale;
diffc sol in cold ale; insol in w; was prepd by Bis(methylphenylamino)-ethane and Derivatives
nitrating 2,4-bis(methylamino)-3, 5-dinitrotoluene. 2. Bis[(2’, 3’ or 4 )-met bylpbenylamino] -etbane
Its expl props were not detd or 1,2- Bis[(2’,3’ or 4’) . methylanilino]- ethane
Re/s: l)Beil 13,(42) 2) J. J. Blanksma,Rec 29, [called N.N’-Di(o,m or p-)-tolyl-iithylendiamin
413(1910) in Ger], H3C,C6H4 .NH. CH2. CH2.NH.C6H4 ,CH3;
2,4.Bis(methylnitrosamino).3,5.dinitrotoluene, mw 240.34, N 11.66%. Three isomers are de-
CH3 .C6 H(N02)2 [N(NO).CHJZ; mw 298.22, N scribed in the literature. All form tryst salts.
28.18%; almost COI Ifts(from ale), mp 132°, Other props and method of prepn are given in
very stable compd,; partly decompd by boiling Beil 12, 825,868, & 974
with AcO}I; was prepd by treating either 2,4 1, 2- Bis(4’. metbVl-2’, 6’ .dinitropbenylamino)-e tbane
-bis(methylamino)-3,5 -dinitroto1uene or 2-methyl- H3C(02N)2C6H2.NH. CH2.CH2.NH.C6H2 (NO J2.-
amino-3, 5-dinitro-4-methy lnitrosamino-toluene CH3; mw 420.34, N 20.00%; orn lfts(from dil
with Na nitrite. Its expl props were not detd dioxane), mp 233°; can be prepd from 4-methyl
Refs: l)Beil 13,143 2) A. Sommer, JPraktChem -2 ,6-dinitroanisole and 1,2-diaminoethane(Ref
67,560(1903) & JCS 84 1,657(1903) 2). The nitration of 1,2-bis(2’ or 3’-methyl-
3,5.Bis(methylamino).2,4,6-trinitrotoluene, phenylamine)-ethane to give tetranitro derivs
CH3. C6(N02)3(NH. CH3)2; mw 285.22,, N 24.56%: of undetermined structure had been described
red trysts (from aIc), mp 156°; was ptepd by earlier in the literature(Ref 1)
heating an alc soln of 3, 5-dibromo-2,4,6-tri- Re/s: l)Beil 12,826 & 868 2)W.L. C. Veer,Re c
nitrotoluene with methylamine in a closed tube 57, 1006(1938)
Refl Beil 13,165
3,5-Bis(methylnitramine).2,4,6.trinitrotoluene,
CHg. C6(N02)3[N(N02) .CH~z; mw 375.22, N l,2-Bis[N-(4’-methyl-2’,6’-dinitrophenyl)-ni-
26.13%; CO1 trysts, mp 199-200°(dec), expl tramino]-ethane,
when heated on a Pt foil in a flame; can be H3C.(N02)2 .C6H2.N(N02).CH2 .CH2.N(NOJ-
prepd by heating either 3, 5-bis(methylamino)- C6H2(N02)2.CHg; mw 510.33, N 21.97%;
2,4-dinitrotoluene or 3, 5-bis(methylamino )-2,- trysts, mp 229-230°, expl on heating to
4,6-trinitrotoluene with nitric acid of d 1.52 higher temp; was prepd by nitration of either
Re/s: I)Seil 13,165 2) J. J.131anksma,Rec 23, 1,2-bis(4 ‘-methyl phenylamino)-eth ane(Ref 2) or
127(1904) & JCS 86 1,566(1904) 1,2-bis(4’-methy l-2 ‘,6 ‘-dinitrophenyl amino)-eth-

—.—.. —.—
 B 151

ane(Ref 3) N 53.34%; wh rhombs, mp 275°; was prepd by

Refs: l)Beik not found 2)A.E.Schouten,Rec boiling for 2 hrs, 2 mols of 3-amino-5-methyI-s
!56,560(1937) 3)W.L.C.Veer,Rec 57,1006 -triazole with an excess of over 1 mol ethyl
(1938) orthoformate, followed by cooling. This high
-nitrogen compd was patented as a stabilizer for
Bis(methylphenylamino)-propane and Derivatives,
photographic emulsions. Its expl props were
1, 3. Bis[(2’ or 4’)-rnet ~ylpbenylamirzo]- propane
not investigated
or I, 3. Bis[(2’ or 4“)-metby~anilino]- propane
Re/s: l)Beil- not found 2)J .D.Kendall &
[called a.y-Di(o or p)-toluidino-propan or N.N’
H. G. Suggate,USP 2, 534,914(1950)& CA 45,
-Di(o or p)-toIyI-trimethy lendiamin in Ger]
2350(1951) 3)Ibid,USP 2,588,538(1952) &
H3C.C6H4.NH.CH2 .CH2.CH2.NH.C6H4 .CH3;
CA 46,4405-6(1952)
mw 254.36, N 11.01%. Two isomers are listed
in Beil 12,828, & 977 Bis(3-methyl-2,4,6-trinitrophenyl)-amine.
1, 3- Bis(4’. methyl-2’, 6’-dinitropheny lamino)-
See 2,4,6,2 ‘,4’,6’-Hexanitro-3,3 ‘-dimethyl-di-
propane, H~C(02N)2C6H2 .NH.CH2.-CH2.CH2.-
phenylamine; Vol l,p A443-R
NH. C6H2(N02)2CH9; mw 434.36, N 19.35%:;
golden yel scales(from acet+ some et acet), mp
Bis(naphthyl)-succinamide and Derivatives
2060; was prepd by boiling in alc soln 4-methyl
Bis(a- napbtbyl)-succinamide( called Bernstei m
-2,6-dinitroani so1e with 1,3-diaminopropane.
saure-bis-a-naphthamid or N. N’-Di-a-naphthyI
This compd gives an expl nitramine deriv
-succinamid in Ger),
on nitration
C10H7.NH.C0.CH2 .CH2.C0.NH.C1 J-I,; mw
Re/s: l)Beil- not found 2)W.L.C.Veer,Rec
368.42, N 7.60%; ndls(from AcOH), mp ca 285°
57,1006(1938)
(dec); S1 sol in w or ale; diffc sol in AcOH;
1,3-Bis[N-(4’.methyl-2’96'-dinitrophenyl)-
other props and method of prepn are given in
nitramino]-propane,H3C.(02N)2C6H2.N(N02 ).-
Beil !2, 1235
CH2.CH2 .CH2.N(N02 ). C6H2(N02 )2CH3; mw
Bis(mononitro- a.naphtbyl)-succinamide,
524.36, N 21.38%; pale yel trysts, mp 181°
C24H1 *N406, not found in Beil or in CA thru
(decomp at a lower temp if impure); expl on
1956
heating to a higher temp; sol in dioxane; S1
N, N ‘-Bis(x, x-dinitro-a-napby tbvl }- succinamide,
SOI in boiling ale, chlf or benz; insol in w, eth
(02N)2C10H~.NH. C0.CHz.CH2.C0.NH.C 10H5-
or petr, eth; was prepd by nitrating either 1,3
(N02)2; mw 548.42, N 15.33%; yel ndls(from
-bis(4’-methylphenylamino)-propane or 1,3-bis(4’
AcOH), mp ca 22 fldec); insol in w or ale; was
-methyI-2’,6’-dinitrophenylamino)-propane
Re/s: l) Beil- not found 2)W.L.C.Veer,Rec prepd by treating the parent compd in AcOH
57,1005-1006 & 1013(1938) slurry with HN03, as described in Beil 12,
1264
BiS(l-methyl-l,2,3,4-tetrazolyl-5)-diazene; N,N’-Bis(x,x,x,x-tetranitro-a-naphthyl)-suc-

5, 5’-Azobis(l -methyl. 1,2, 3,4- tetrazole) or cinamide,(02N)4C10H3.NH CO.C~ .CH2.C0.-

1, 1‘-D imetbyl-5, .5’-azotetrazole (called Dimethyl NH. C10H3(N02)4; mw 728.42, N 19.23%; micro-
-1. l’-azo-5.5’-tetrazol in Ger), cryst yel mass, rnp 256°(dec); insol in cold
~–N(CH3)–$-N:N-C-N(CH3 )–~; mw 194.17, AcOH; was obtd on nitrating the parent compd
N ---~ -.-N A N with HN03
N 72.14%; orn-yel c~sts, mp 182(dec), expl Refs: l)Beil i2,1265 2)H.Hiibner,Ann 209,384
sharply in contact with a flame or by friction; (1881)
was prepd by shaking & warming on a steam
Bis(ß-nitraminoethyl)-amine. See under Bis($
bath methyl-5-aminitotetrazole with a dil aq soln
of Ca hypochlorite. Reduction gave the Hydrazo -aminoethyl)-amine
deriv, tryst + H30, mp 158°(dec)
1,2-Bis(2-nitramino-2-imidazolin-1-yl)-ethane.
Re/s: l) Beil-not found 2)R.Stoll< et al, JPrakt-
Chem 134,287(1932) & CA 26,5565(1932) See under Aminoimidazoline and Imidazoline
Substituted Derivatives; Vol l,p A220-R
N.N’.Bis(5-methyl-s-triazol-3-yl)-formamidine or
l,2-Bis(2-nitramino-3-nitro-1-imidazolidyl)-ethane.
3, _3’-Bis(5 -methyl- lH- 1, 2,4-triazolyl)- formamidine,
See under Aminoimidazoline and Imidazoline
H~C.$-N=~-N:CH.NH–$-N-C. CH3; mw 206.21,
N—NH HN—fi Substituted Derivatives; Vol l,p A220-R
 B152

3,3-Bis(nitratomethyl)-butene-1. Same as 3,3 N,N’-Bis(nitroxymethyl)-ethylenedinitramine.

-Di(nitratomethy l)-butene-l See under N, N’-Di(methylol}-ethy lenediamine

Bis(p-nitrobenzoyl)-furoxan. See Di(p-nitro- Bis(nitroxymethyl)-methylaminomethane See

benzoyl)-furoxan under Dibenzoylfuroxan 2-Amino-2-methyl- 1,3-propanediol Dinitrate
under Aminomethylprop anediols in Vol 1,p A232
Bis(nitrobenzoyl)-peroxide, See Di(nitrobenzoyl) -R
-peroxide under Dibenzoylperoxide
N,N’-Bis(ß-nitroxypropyl)-nitramine. See under
2,2-Bis(3-nitro-5-methyl-4-hydroxypheny l)-propane N, N-Di(propylol)- amine
or Di(3-nitro- .5-me thyl-4- bydroxypbenyl)-dime tbyl-
methane, (02N) (HO) (CH3)C6H2.C(CH3 ) C5H2- Bis(penta-fluorosulfur) Peroxide,(SF5)202, col
(CH3) (OH) (N02); mw 346.33, N 8.08%, ~B to Iiq,fr p -95.4, bp 49.4°; it is one of the useful
C02 -171%; yel trysts, mp 195-196°; can be reagents for producing certain peroxides.
prepd by condensation of o-cresole with acet(in Its prepn and props are described in detail by
H2S04 ) followed by nitration C. LMerriH and G. H. Cady,Univ of Washington
Its salts can be used in ignition compositions (Seattle ),Tech Rept No 27(1960) (9pp) (to Office
Re/.s: l)Beil- not found 2)DuPont,BritP 431- of Naval Research)
945(1936) & CA 30,109(1936)
1,2-Bis(Phenylamino)-ethane. See Bis(anilino)
Bis(nitrophenyl)-nitrosamine. See Di(nitrophenyl)- -ethane
-nitrosamine under Diphenylamine
Bis(phenylamino)-ethanol. See Di(phenyl)-amino

l,5-Bis(p-nitrophenyl)-lH-tetrazole. See Di(p

-N-ethanoI
-nitrophenyl)-lH-tetrazole under Diphenyltetrazole
1,3-Bis(phenylamino)-propane. See Bis(anilino)

l,4-Bis(nitrosohydroxylamino)-benzene. See -propane

under Di(hydroxylamino)-benzene
4,4’-Bis(phenylazo)-azoxybenzene. See Bis-
(benzene azo)-azoxybenzene
Bis(nitrosohydroxylamino)-methane, See under
Di(hydroxylamino)-methane
Bis(phenylazobenzene). See Bis(benzeneazo-
benzene)
Bisnitrosoimidazoline, See under Biimidazoline

N,N’-Bis(phenylazo)-cyclo-2,3,5,7-penta-
Bis(ß-nitroxyethyl)-amine Nitrate. See under
methylene-1,4-diamine or N, N’-Bis(pbenylazo)
Di(ethylol)-amine
-etbylenetrim etbylenediamine {called N. N’-Bis
-benzoldiazo-[athy len-trimethylen-diamin] in
Bis(ß-nitroxyethyl)-amine P icrate. See under
Ger}, CH2 CH
Di(ethylol)-amine 2\
C6H~N:N.N< N. N:N.C6H5;
N,N’-Bis(ß-nitroxyethyl)-ethylenedinitramine.
CH2—CH2—CH<
mw 308.38, N 27.255%; yel crysts(from alc or
See under 1,3-Di(~-ethylol)-ethy lenediamine
ligroin), mp 118°; was prepd by treating a
Bis(nitroxyethyl)-nitramine or DINA. See Di-
benzenediazonium sulfate soln with a HCI
soln of ethylene in lN NaOH. Other props are
ethanolnitramine Dinitrate under Di(ethylol)
-amine given in the Refs. This compd can probably
be nitrated to give expl derivs
Refs: l)Beil 23,17 2)W. Esch & W. Marckwald,,
Bis(ß-nitroxyethyI-N-nitro)-oxamide or NENO.
See under Di(ethylol)-oxamide
Ber 33,761(1900) & JCS 78 1,336(1900)

Bis(phenylazo)-dihydroxy-naphthalene and
Bis(ß-nitroxyethyl)-oxamide. See N, N’-di(2
Derivatives
-nitroxyethyl)-oxamide under Di(ethylol)-oxamide
Bis(pbenylazo)-diby droxy-napbtbalene (called
Bis-benzolazo-dioxy -naphthalin in Ger),
 6153

(C6H5.N:N) (HO)C10H4(0H)(N: N. C6H5); 2,4-Bis(4-nitrophenylazo).5-nitro-l-naphthol,

mw 368.38, N 15.2 1%. Several isomers are C22H1a N707, mw 487.38, N 20.12!%; dk trysts
described in Beil 16,200,201,(277,278) & [87] (from benz or acet+w), mp 265 ~ mod sol in
1,8-Bis(4-nitrophenylazo)-2,7-dihydroxy benz or toluene; S1 sol in anisole or acet:
-naphthalene[called 1.8- Bis(4-nitro-b enzolazo) diffc sol in a Ic; insol in alkalies; dissolves in
-2.7-dioxy-naphthalin in Ger], in coned Hz SO@ giving a green color; was
(02 N.C6H4.N:N)(HO)C1 ~H4(OH) (N: N. C6H4. prepd by treating 4-nitrobenzene <i-azo-4>-5
N02); raw 458.38, N 18.34%; crysts(from nitro. -nitro-l-naphthol in alc soln with 4-nitro -
benz), mp dec above 300°; sol in anisole, benzene- 1-diazoniumchloride. Its expl props
pyridine, nitrobenz or dimethylaniline; sol in were not investigated
alkalies and in coned H2S04, giving a brn-red Refs: l)Beil 16,162 2) F. Kaufler & E. Braure,
color; 51 sol in xylol, almost insol in toluene Ber 40,3272(1907) & JCS 92 I, 799(1907)
and glac AcOH; was prepd from 2,7-dihydroxy-
naphthalene and 4-nitrobenzenediazonium Bis(phenylazoxy)-azoxybenzene. See Bis-
c’hloride in alkaline soln. The mixt of monoazo- (benzeneazoxy)-azoxybenzene and Derivatives
and bisazo- compds is separated by means of
the greater volubility of the former in toluene Bis(p-phenylbenzoyl)-furoxan, CZ8H18N204.
Refs: l)Beil 16,202 2) F. Kaufler & E. Its props and methods of prepn are given in
Brauer,Ber 40,3275(1907) & JCS 92 1,799(1907) Conf ADL,’cSynthesis and Testing of High
Note: Higher nitrated derivs of the parent comp Explosives”, 3rd Rpt(1953),p 384 and 4th Rpt
were not found in Beil or in CA thru 1956 (1956),p 58

N, N’-Bis(phenylazo)-ethylene-trimethylene Bis(phenyl)-ethylenediamine. Same as Bis-

-diamine. Same as N, N’- i3is(phenylazo)- cyclo (anilino)-ethane
-2,3,5,7-pentamethy lenel,4-diamine
Bis(phenyl)-ethyleneglycol Ether and
Bis(phenylazo)-glycine and Derivatives Derivatives
N,N’-Bis(phenylazo)-glycine[called Bis(benzene- Bis(pbenyl)-etby leneglygol Ether or 1, 2-Di-
diazo).glycocoll in CA ‘Ref and Bis(benzol- pherzoxy-etharze (called Athylen-glykol-di-
diazo)-glykokoll or Diphenyl-pentazdien-e ssig- phenylather or a./3-Diphenoxy-Hth?n in Ger),
saure in Ger], CSH5.0.CH2 .CH2.0.C6H5; mw 214.25, is
(C6H~N:N)2N.CH2. COOH; mw 283.28, N described in Beil 6,146 & [ 150]
24.72%; trysts mm expl 124°; was prepd from Bis(mononitropbeny l)-etbyleneglycol Ether or
glycine(amino-acetic acid), NaOH and benzene- 1, 2- Bis(nitropbenoxyJ ethane [called Athylen
diazonium chloride at 0° .glykol-bis(nitro-pheny lather) in Ger], 02N.C6H4 .O.-
N,N’-Bis(4-nitophenylazo)-glycine, CH2.CH2.0.C6H4. N02; mw 304.25, N 9.21%. Three
(02N.C6H4. N:N)2 N. CHZ.COOH; mw 373.29, N isomers are described in Beil 6,219,224,232 & [223]
26.27%; yel trysts, mp expl 166-7°; was obtd as Bis(2,4-dinitropbe nyl)-etbylenegly cal Ether
26% of the product from the reaction of p-02N.- q? 1, 2- Bis(2,4-dirz itropbenoxy)-e thane)[called
C6H4N2CI with 3 mols of O. lN NaOH, together with Athylen-glykol-bis( 2.4-dinitro-phenylather) in Ger],
20% of p-02 N.C6H .,.N:NNHC~H4 .N02-P (02 N)2C6H3.0. CH2, CH2.0. C~Hs(N02)2; mw
Refs: l) Beil- not found 2)M.Busch et al, JPrakt- 394.25, N 14.21%; lt yel crysts(from acet or
Chem 140, 117(1934) & CA 28,5425( 1934) phenol), mp 215.2°; readily sol in boiling
acet, AcOH or phenol; insol in w, ale, eth,
Bis(phenylozo)-naphthol and Derivatives chlf or benz; was obtd in smaIl quantity by
2,4- Bis(pbenylazo)- l-napbtbol [called 2.4 Fairbourne & Toms(Ref 2) on concentrating
-Bis-benzolazo-naphthol-(1) in Ger], the mother liquor from the AcOH crystn of the prod
H5C6N:N-<H=C(OH)-$ -CH=$H from l-chloro-2,4-dinitrobe nzene in ethylene
CH=$— C-CH=CH; gIycol and an ethylene-glycollic soln of
H~C6.N:N NaOH. Ryan & Kenny(Ref 3) prepd the compd
mw 352.38, N 15.90%; grn-black, intensive by nitration of lower nitrated derivs of bis-
bronze, shiny ndls(from amyl ale) or trysts (phenyl)-ethylenegly col ether using nitrogen
(from chlf+alc), mp 190-2°; other props and peroxide or HN03. Dosios & Tsatsas obtd
methods of prepn are given in Beil 16,161 & this compd by nitration of the parent compd
[254] with fuming HN03 at -10° or by reaction of
the disodium salt of ethylene glycol with an
 B 154

excess of fused l-chloro-2,4-d initrobenzene N,N’-Bis(2,4,6-trinitrophenyl)-guanidine or

(Ref 4). This latter reaction may result in Hexanitrodiphenyl Guanidine,
deflagration but it proceeds smoothly if the (02N)3.C6H2.NH. C(:NH).NH.CGH2( N02)a; mw
disodium salt is added in small proportions 481.26, N 26.20%; no description found; was
R efs: l)Beil 6,[243] 2) A. Fairbourne & H. proposed in 1923 Dy Olsen (Ref 2) as, a booster
Toms, JCS 119 11,2077(1921) & CA I6,1072 charge; was prepd as a mixt of the hexanitro
(1922) 3)H. Ryan & T. Kenny, SciProcRoy- deriv and more highly nitrated derivs by
DublinSoc 17,305(1924); JCS 126 1,505(1924) nitrating diphenylguanidine with mixed nitric
& CA 18,1655(1924) 4)C.Dosios & T. -sulfuri c acid(Ref 3). It was reported, from a
Tsatsas,CR 180,1276(1925) & JCS 1281,655 limited study of its expl props(Ref 2), to be
(1925) comparable to Tetryl but SI less sensitive
l,2-Bis(2,4,6-trinitrophenyl)-ethyleneglycol and about 1/3 more powerful than Tetryl(Refs
Ether or 1, 2- Bis(2, 4,6- trinitrophenoxy )-ethane, 3&4)
(02 N)3C6H2.0.CH2.CH2 .0. C6H3(N02)3; Re/s: l) Beil- not found 2) F.01sen,ArOrdn
mw 484.25, N 17.35%, crysts(from acet+alc), 3,271(1923) & CA 17,2051(1923) 3)D.M. Jack-
mp 197 c; mp fumes and ignites, but not vio- man & F. Olsen,USP 1547815(1925) & CA 19,
lently, on being heated in an open dish; was 3021(1925) 4) Blatt,0SRD 2014(1944)
prepd by nitration of the bis(2,4-dinitro) deriv
in H2S04 using mixed acid at O-1OO. This Bis{[(phenyl-phenylamino)-ethyl]-amino}-ethane
compd does not expl by impact. It was studied and Derivatives
with the expectation of prepg a compd having 1,2- Bis{[(pbenyl)-( pheaylamino)-ethy l]-amino]
expl props similar to trinitroanis ole(qv,VOl 1, -etbane, C30H30N4. Although not found in the
p A450ff) but without unfavorable toxic effects literature it may be considered as a parent
of the Iatter compd of its nitro derivs
Refs: l) Beil- not found 2)cA- not found 1,2-Bzs.{[ (2’’’,”’” .Dinitropbenyl)-(2 “,4“-di-
3)R. C. Elderfield,0SRD 907(1942),p 8(PB No nitropbenylam ino)-etbyll- amino l-etbane,
31085) C90H26N12016, mw 810.59, N 20.74%; brn
-yeI tryst powd, insoI in the common SOIVS;
Bis(phenyl)-guanidine and Derivatives was obtd by treating triethylene tetramine with
N, N’-Bis(pbenyl)- guanidine or N, N’. Diphenyl l-bromo-2 ,4-dinitrobenzene and Na acetate in
-guanidirze(called N. N’-Diphenyl-guanidin in alc soln(Ref 2,p 415)
Ger), C6H5.NH. C(:NH).NH.CGH5; mw 211.26, On nitration it gives the following ex-
N 19.89%; ndls(from ale) or monoclinic prism~ plosive:
mp 151.5°, It is described in Ref 1. Forms
l,2-Bis{[(2’’’,4''',6'''-trinitrophenyl)-(2",4",6"
numerous salts and addn compds. According
-trinitrophenylnitramino)-ethyl]-amino}-ethane
to Sax(Ref 2), its toxicity details are unknown
or 1, 10-D initro- 1,4,7,1 O-tetra(2,4, 6-trinitro-
Re/s: l)BeiI 12,369,(236) & [216] 2)Sax
pb enyl)- 1,4,7, 10-tetrazadecane,
(1957),p 640
(02 N)3H2CG.~. CH2.CH2.~.CH2.CH2.-
N,N’-Bis(mononitrophenyl)-guanidine,
N02 C~H2(N02)3
02 N.C6H4 .NH.C(:NH).NH.C6Ha .N02; mw
y. CH2.CH2— N. C6H2(N02)~; mw 1080.59,
301.26, N 23.2 S%. Two isomers are described
CGH2(N02)3 N02
in the literature: N, N’” Bis(3-nitrophenyl)
N 23.33%; lt yel tryst pdr, mp dec with evoln
-guanidine, flakes, mp 196-197°(Ref 1) and
of gas; expl when heated suddenly; was prepd
N, N’-Bis(4-nitropb enyl)-guanidine, prisms
by treating the above bis(dinitro-dinitro-)
(from ale), mp ca 222°, resets and is still
compd, C30H ~N1201G, with abs nitric acid,
solid at 295 °(Refs 2 & 3). Other props and
cooled to -153(Ref 2,p 415-16)
methods of prepn are given in the Refs
Refs: l) Beil- not found 2) J.van Alphen,Rec
Refs: l)Beil 12,707 & [381] 2)Beil 12,[393]
3)W. J .S.Naunton,Tran sInstRubberInd 2,147-166
55,415-16(1936) & CA 30,5992-3(1936)
(1926); JSCI 4!i,378T(1926) & CA 21,672
(1927) a#*Bis(a*phenyl@ *picryl*hydraz ino)Oethane
[called a.@-Bis(a-pheny l-@-pikryl;hydrazino)
N, N*-B is(dinitropheny l)-guanidine,
-athan or Na.Na’ -Diphenyl-N ~ .N~ -dipikryl
(0, N),.C6H3 .NH.C(:NH).NH.Ce H3 (NO* )2; not
-athytendihydrazin in Ger],
found in Beil or in CA thru 1956

—. —-—.——. ——— .—.— —.———.-——-

 B 155

[(02 N)3CGH2.NH.N(C6 H5). CH2-12; mw 664.50, Although not found in the literature, may be
N 21.08Z; brick-red trysts from et acet), mp considered as a parent compd of nitro deriv
ca 202.5° when it blackens and foams; diffc described below
sol in boiling ale; insol in eth or benz; was prepd 2,4-Bis(2’,4’,6’-trinitrophenylthio)-l-ethyl-
from picryl chloride and phenylethylene hydrazine. benzene or 2,4-Di(picrylthiol)-l-ethylbenzene
Its expl props were not detd [called 2.4-Bis(2.4.6~~ rinitro-phenylmercapto)
Refs: l)Beil 15,496 2) M. Hischmann, Ann -1-athyl-benzol or 4-Athyl-dithiore sorcin-di-
310,161(1900) & JCS 78 1,251(1900) pikrylather in Ger],
C2H~.C6H3[S.C6H2 (N02)3]2; mw 592.48, N
Bis(phenylthio)-dimethylbenzene and 14.19%; dk yel ndls+l mol C6H6(from benz),
Derivatives mp 197.5-199°, becomes benz free ca 100°;
Bis(pbenyltbio)-dirnetby lberazene, C20H1 ~S2. readily sol in benz, AcOH & et acet; diffc sol
Although not found in the literature, it may in ale; was obtd by boiling an alc soln of 2,4
be considered as a parent compd of its nitro -dithio-l-ethylbenzene with picryl chloride.
deriv~ Its expl props were not detd
Bis(2,4,6-trinitrophenylthio)-dimethylbenzene Refs: l)13eil 6,(441) 2) J. Pollak,Monatsh
or Di(Picrylthiol)-zylene, 39,187 (1918 );Jcs 114 1,499(1918) & CA 13,
(CH3)2C6H2[S.C6 H2(N02)~]2; mw 592.48, N 419(1919)
14.19%. The following isomers are described
in the literature: 2,4- Bis(2* 4’, 6’-trinitropbenyl- l,3-Bis(phenyltriazeno)-benzene or 3,3’-m
tbio)-1,3-dimetby lbenzene[called 2.4-B is(2.4.6 l-Phenylene-bis(1-phenyltriazene) (caIled
-trinitro-pheny lmercapto)-l. 3-dim ethyl-b enzol 1.3-B is-phenyltriazeno-benzol in Ger),
or 2.4-D imethyl*dit,hiore sorcin-dipikrylather in H5C6.HN.N:N.C6H4 N: N. NH. C6H5; mw
Ger], yel crysts(from AcOH), mp 211-213°; 316.36, N 26.57%; yeI crysts(from aIc), mp
was obtd by warming 2,4-dithio-1,3-dime tiyl- 161°, expl on rapid heating; dec violently in
benzene with 2 mols of picryl chloride in alc cold AcOH; was prepd by reacting l,3-di-
(Refs 1 & 2,p 142). Its expl props were not azidobenzene and phenylmagne siumbromide
detd in ether. Its Silver salt, brown powd, expl on
4, 6-B is(2’, 4’, 6* .trirzitroph enyltbio )- 1, 3-di- heating without me Iting
metby~benzene, orn-col trysts+ 1 mol C~H6 Refs: l)Beil 16, [356] 2) H. Kleinfeller,
(from benz), mp 258-259.5°; sol in AcOH, et JPrChern 119,66(1928) & CA 22,2566(1928)
acet or benz; diffc sol in ale, eth, chlf or
petr eth; was prepd by warming 4,6-dithio-l,- Bis(phenyl)-urea and Derivatives
3-dimethylbenzene with 2 mols picrylchloride N, N’-Bis(pbenyl)- urea; 1,3-D iphenyl-urea or
in alc(Refs 1 & 2,p 138) Carbanilide (called N. N’-Diphenylharnstoff or
2, 6- Bis(2’, 4’, 6*-trinitropbeny ltbio)- l,4-dimetbyl - Carbanilid in Ger), C6H5.NH.C0.NH.C6 H5;
benzene, yel crysts(from et acet), mp 251-255°; mw 212.24, 13.20%. Its prepn and props are
sol in AcOH or et acet; S1 sol in ale. It was given in Beil 12,352,(233) & [207]
prepd in the same manner as the other isomers iV, N’. Bis(mononitropbe nyl)-urea; Dinitro-sym
(Refs 1 & 2,p 147). Its expl props were not -dipbenyl-urea or Dinitrocarban ilide,
detd 02 N. C6H4.NH. CO.NH. C6H4. N02; mw 302.24,
N 18.54%. Three isomers are described in
3,5. Bis(2’,4’, 6’-trinitropbenyltbio). l,2-dimetbyl-
Beil 12,695,706,723, (343,348,353) & [381,393]
benzene(listed in CA Coil Formula Index as
3,5-Ditbio-o-xy lene-dipicrate), mp 202-203° N,N’-Bis(dinitrophenyl)-urea; Tetranitro-~Ym
(dec); was prepd and described in Ref 3. Its -dip benyl-urea or Tetranitro-carb anilide,
expl props were not detd (02 N)2CGH~.NH. CO. NH. C6H~(N02)2; mw
Refs: l)Beil 1,(445,446) 2) J. Pollak & B. 392.24, N 24.43%. Two isomers are described
Schladler,Montsch 39,138,142,147(1918); JCS in the literature: N, N ‘-B is(2, 4-din itropbenyl)
114 1,497-498(1918) & CA 13,418-419(1919) -urea, yel ndls(from coned HNOa ), mp begins
3) J. Pollak et al, Monatsh 55,358-78(1930) & to dec ca 150°, melts ca 218 wit]] decomposi-
CA 24,4005(1930) tion(Ref 1); and N, N’-Bis(3,5- dinitropbenyl)
-urea, yel ndls(fro,m alc+w), mp 265° (Ref 2).
Bis(phenylthio)-ethylbenzene and Derivatives Other props and methods of prepn are given
2,4- Bis(phenylthio)- l-ethylbenzene, CZOH ,eSz. in the Refs. Expl props of these tetranitro
 I

B 156

compds were not detd C22H16NZ04, dk yel ndls(from AcOH), mp

Refs: l)Beil 12,755,(363) & [41O] 2]Beil 12,759 186°; was prepd by heating 4,6-d initroxylene
with benzaldehyde in presence of piper adine
N,N’-Bis(2,4,6-trinitrophenyl)-urea; sym-Di- Refi Beil 5,(360)
picryl-urea or 2,4,6,2’,4’,6’-Hexanitrocarb- 1, 3- Bis(styryl)-2,4, 6-trinitrobenzene (called
anilide[c.ailed N. N’-Dipikryl-harn stoff; 2.4.- 2.4.6 -Trinitro-l .3-distyryl-benzol in Ger),
6.2’.4’.6 ‘-Hexanitrocarbanilid or 2.4.6 .2’.4’.6’ C6H5,CH:CH.C6H(N02 )3. CH:CH. C6H~;
-Hexanitro-symm-dipheny lharnstoff in Ger~ mw 417.36, N 10.07%; yel ndls(from AcOH),
(02 N)3.C6H2.NH.C0. NH. C6H2(N02)3; mw mp 147-148°; readily SOI in benz or ACOH;
482.24, 23.24%; almost COI crysts(from acet+ SI sol in acet or chlf; diffc sol in ale; was
petr eth) or ndls(from acetonitrile); mp begins prepd from 2,4,6 -trinitro-m-xylene, benzalde-
to dec ca 140°, dec 203-209°, expl spontane- hyde and a little pi peridine by boiling in
ously at 345°; readily sol in hot nitrobenz; in amyl alc soln
warm dil H2S04, yields picric acid; in boiling Re/s: l)Beil 5,(360) 2)W. Borsche, Ann 386,
ammonia, yields Trinitroaniline; can be prepd 369(1912) & JCS 102 1,180(1912)
by nitration of N, N’-bis(phenyl)-tuea in one, l,3-Bis(4-nitrostyryl)-2,4,6-trinitrobenzene
two or three stage s(Refs 1 & 3) and by other [called 2.4.6 -Trinitro-l.3-bis( 4-nitro-styryl)
method s(Refs 1 & 2) -benzol in Ger],
According to Davis(Ref 3) this compd is a 02 N. C6H4.CH:CH.C6H( N02)3.CH:CH.CGH4-
brisant high expl suitable for use in boosters, N02. mw 507.36, N 13.80%; brownish ndls
detonators, detonating fuses, primer caps, etc. (fro; acet+alc), mp 268 °(dec); sol in acet;
It requires 0.19 g of MF to detonate a 0.4-g SI sol in boiling AcOH or chlf; insol in alc or
sample in the Sand Test and is S1 more brisant
benz; was prepd by heating 2,4,6 -trinitro-m
than TNT. In the drop test, it is about the
-xylene with p-nitroben zaldehyde in presence
same in sensitivity to impact as Tetryl
of plperdine
Re/.s: l)Beil 12,768,(370) & [423] 2)R.I.C.
Refs: l)Beil 5,(361) 2) W. Borsche, Ann 386,
Loh & W. M. DehnJACS 48,2958(1926) & CA
372(1912)
21,67(1927) 3)Davis(1943),pp 188-189
Note: No higher nitrated derivs of the bis
(styryl)-2,4,6-trinitrobenzene were found in
Bis(phthalic acid)-peroxide (called Saures
Beil or in CA thru 1956
Phthalperoxyd; PeroxydphthaIsaure or Phthal-
superoxydsaure in Ger),
Bis(succinyl)-peroxide; Disuccinyl Peroxide
, Co. oo.co ,
H/ Bis(succinic acid)-peroxide; or B is(3-carboxy -
c
6 4, ‘C6H4; mw 330.24, 0
propionyl).p eroxide [called Bis(~-carboxy
COOH HOOC’
-propionyl)-peroxyd; Saures Succinperoxyd or
38.76%; ndls, mp 156 °(dec), expl on heating
Succinsuperoxydsaure in Ger],
to higher temps; cfiffc sol in all org SOIVS;
HOZC. CH2. CH2. CO.O.CO.CHZ .CH2.COOH;
was prepd by treating an aIkaIine soln of
mw 234.16, 0 54.66%; pltlts, dec slowly on
monoperphthalic acid(C02H. C6H4. C03H)
long exposure to air and light; mp softens at
with phthalic anhydride or by the direct
115°, melts with decompn ca 128°, expl on
action of H202 on finely divided phthalic
contact with open flame; sol in W, ale, acet
anhydride in the presence of NaOH
or et acet; diffc sol in eth; sinol in benz,
Re/s: l)Beil 9,804 2) A. Baeyer & V. Villager,
chlf or ligroin; was prepd by Clover &
Ber 34,763(1901); JCS 80 1,326(1901)
Houghton(Ref 2) from an excess of succinic
anhydride added to a soln of H202 below 30°
1,5-Bis(Picrylamino)-anthraquinone. See 1,5
(Ref 1)
-Bis(2,4,6-trinitro ani1ino)-anthraquinone under
The aq soln of this peroxide gradually
Bis(anilino)-anthraquinone
undergoes hydrolysis, forming persuccinic
Bis(styryl)-benzene and Derivatives
acid, C02H. CHZ. CH2. C03H, and succinic
acid. It liberates iodine rapidly from KI and
Bis(styryl). benzene or Distyryl. berzzene,
oxidizes a manganous salt to permanganate.
C22H,~. One isomer 1,4-B is(styryl)-benzene
When heated with boiling xylene, it dec into
is described in BeiI 5,(361)
C02, succinic anhydride, succinic acid,
4,6- Dinitro- 1,3. bis(styryl)- benzene,
adipic acid and a gummy acidic substance
 B 157

(Ref 2). Reynhart(Ref 3) found that this per- 1936,N0 5, 42pp & CA 31,4987(1937) 7)Blatt,
oxide, when decompd at 280°, gave 58% adipic OSRD 2014(1944) 8)W. Friederich,USP2710297
acid and 37% C02 (1955) & CA 50,5768(1956)
Polarographic studies of bis(succinic acid)
-peroxide were made by Willits et al(Ref 6) Bis(5-tetrazole)-hydrazine or 5,5’- Hydrazo
and by Bernard(Ref 8). Its use as a polymeriza- -bistetrazole {called N. N’-Bis[tetrazoly l-(5)]
tion catalyst(Ref 4), particularly for tetrafluor- =hydrazin or Bis-tetrazoliny liden-hydrazin in
ethylene, has been the subject of several Ger],
patents(Refk 5,7 & 9) ~-NH–$:N.N:~-NH-$J or
Re/s: l)Beil 2,613 & [553] 2) A. M. Clover & N —NH NH—N
A. C. Houghton, AmChemJ 32,55(1904) & JCS ~-N=$.NH.NH. $=N-~; mw 168.13, N 83.32%:
86 1,707-43(1904) 3) A. F. A. Reynhart,Rec 46, N— NH NH—N
71(1927) & CA 21,1454(1927) 4)C.S.Marvel wh amor powd, mp 240-241° dec(Ref 4), expl
et al, JPolymerSci 3’,433(1948) & CA 42,8014 on heating to higher temp; Q; 459.9kca1/mol
(1948) 5)M.M.Renfrew,USP 2534058(1950) & (Ref 3); Qf at 25°, 135kcal/mol(Ref 3); diffc
CA 45,2262(1951) 6)C.O.Willits et al, Anal- sol in boiling W; insol in org SOIVS; pptd by
Chem 24,785(1952) & CA 46,7934(1952) 7)S. ammonia or alkalies from its soln in coned
G. Bartkoff,USP 2612484(1952) & CA 47,3618 HC1 to yield ppts with many metallic salts;
-9(1953) 8)M.L. J. Bernard, AnnChim(Paris) 10, was prepd from t~e Na salt of 5,5 ‘-azotetra-
315(1955) & CA 50,9175(1956) 9)A. E. Kroll, zole by boiling with Mg powd or better by
USP 2750350(1956) & CA 50,13507-8(1956) treating with a S1 excess of Zn chloride in
10)Sax(1957),l143 HC1 soln(Refs 1 & 2)
5,5’-Bis(a-or l,2,3,4-tetrazole) or j,j’.Bi(lH The alk soln of bis(5-tetrazole )-hydrazine
. I, .2, 3,4.te trazole) [called Ditetrazolyl-(5 .5’) is oxyd rapidly in the light to 5,5’-azotetra-
in Ger], ~-NH-C- $-NH-~; mw 138.10, N zole. The Ag, Hg+ and Hg++ salts, by boiling
N —i N— N with dil HCI, are converted to the correspond-
81.15%; CO1 prisms(from w), mp 254-255°(dec); ing salts of 5,5’ -azotetrazole(Refs 1 & 2)
mod sol in aIc or acet; S1 sol in eth; insol in McBride et al(Ref 4) studied the potentio-
benz, chlf or petr eth; dec on warming in metric titration of this compd & other org
coned H2S04; was prepd with other products derivs of hydrazine with K iodate
by the action of HN3 on cyanotetrazole, obtd Refs: l)Beil 26,4o8 2) J. Thiele,Ann 303,66
from HNa and dicyan(Ref 2) and by other (1898) & JCS 76 1,171(1899) 3)W.S.McEwan
methods(Refs 1,3,5,6 & 8) & M. W. Riggs, JACS 73,4726(1951) & CA 46,
Bistetrazole forms many salts, some of 4350(1952) 4)W.R.McBride et al, AnalChem
which are expl: Copper salt, CUC2N8, blue 25,1044(1953) & CA 47,9863(1953)
ndls, expl violently on heating; Mercury salt
expl violently; and Silver salt, Ag2C2NQ, yel 3,6-Bis(2H-tetrazolyl-5)-dihydro-1,2,4,5
powd, expl on heating(Refs 1,3,4 & 6) .tetrazine or 3, 6.Di( 2H-tetrazolyl- 5)-dihycfro
Rathsburg(Ref 5) patented the use of bistetra- -syrmte trazirze{ called 3 .6-D i[tetrazolyl-(5)]
zole and its metal salts as components of -dihydro-l .2.4.5 -tetrazin in Ger],
primer or detonator compns(Ref 7) ,NH-NH
Refs: l)Beil 26,(199) & [362] 2) E. Oliveri HN-N=C-C \C-C=N-~H or
-hlandal~ & T. Passa.lacqua,Gazz 43 II, 468 1$-h ~N_ NZ ;T—~

(1913) & CA 8,1272(1914) 3) J. Lifschitz & ~N-NH,

W. F. Donath,Rec 37,279(1918) & CA 13,708 H~-N=C-C C-C= N-~H; mw 220.17,
(1919) 4) E. OIiveri-Mandal~ Gazz 501,257 N==& \NH _N# fi-N
-260(1920); JCS 118 1,504(1920) & CA 14,3412 N 76.35%; yel crysts(dihydrate), mp(loses w
(1920) 5)H.Rathsburg,BritP 177744(1921) & on being heated in vac ca 1300), dec on heat-
CA 16,3399( 1922) ;BritP 185555(1921) & CA ing to higher temp; insol in w, ale, ‘eth, acet,
17,1147(1923); GerP 401344(192 ) & JSCI 44, ligroin or benz; on oxidation Yields 3,6-bis(2H
B28(1925); USP 1511771(1925) & CA 19,178 -tetrazo Iyl-5)- 1,2,4, 5-tetrazine; on heating
(1925); USP 1580572(1926) & CA 20,1907 with coned HC1, decomp into tetrazole, hydra-
(1926) 6)G.Dedichen,AvhandlNorske- zine and C02; was prepd from various derivs
Videnskaps-AkadOs lo, I, Mat-NaturvKlasae of tetrazole, such as 5-cyanotetrazole, by
 B 158

methods given in Refs l,2,3,& 4 85.07%; Iaminates(monohy drate), mp expl on

This compd forms various salts, some of heating; was prepd by treating aminoguanidine
which are expl: Barium salt, BaC4H2N1 z, dinitrate with NaN02 and Na acetate in the
ndls, expl on heating; Dibydruzirze salt, presence of dil acetic acid with cooling; or
2N2H4+C4H4N, ~, It-yel ndls(from w), expl by treating 5-aminotetrazole with NaN02 and
above 280° Na acetate in dil acetic acid, under cooling
Re/s: l)Beil 26,(2ol) 2) J. Lifschitz,Ber 48, This compd explodes on heating or impact.
415-416(1915) 3)T.Curtius et al, Ber 48, It forms salts, some of which are expl:
1619, 1626,1631(1918) 4) J. Lifschitz & W.F. Barium Salt, Ba3(C2N1 , )2+8H20, yel tablets
Donath, Rec 37,282-284(1918) 5) F. R. Benson, (from w), expl mildly on heating; Copper
ChemRevs 41,6(1947) -ammonium salt, CU3(CZN1 , )2+2NH3 , dk-grn
pltlts, expl violently on heating, impact or
Bis[tetrazolyl-(5)]-diimide. Same as Azo- friction; Silver salt, Ag2C2HN1 , +H20,powd,
tetrazole, described in Vol l,pp A659-R to expl violently on heating or on Atrong friction;
A660-L Sodium Salts, several salts are known and
although they are not expl, they can serve as
[N1,N6-Bis(a-.tetrazolyl-5)]-hexazadiene. See starting materials for the prepn of expl salts
Vol l,p A260-R Re/s: l)Beil 26,(190-191) 2)K. A. Hofmann
& H. Hock, Ber 43,1867-70(1910) & Ber 44,
3,6-Bis(2H-tetrazolyl-5)-sym(or1,2,4,5) 2955(1911) 3) E. Lieber & G. B. L. Smith,
-tetrazine{called 3.6-Di-[tetrazolyl-(5)]-1.2.4.5 ChemRevs 25,240(1939) 4)Davis(1943),448
-tetrazin in Ger] 5)F. R. Benson, ChemRevs 41,8(1947) 6)Gilman

HN–N= C-C
ZN–N<
C-C= N-NH; mw 218.16,
4(1953),999-1000

k=== fi IN=N~ fi.--fi

l,3-Bis(lH-tetrazolyl-5)-triazene,Monotriethl
N 77.05%; carmine red Ifts or ndls as dihydrate Lead Salt(called Monotriethyl-lead azoamino-
(from ale), mp(loses w on being heated in vac tetrazole by Burrows et al),
ca 1300), expl on heating at higher temps; ~–NH-:.N:N.NH.C–N[ Pb(C~. CH3)3]-N;
readily sol in w or ale; diffc sol in eth; was N— N I! —.— ..— N
prepd from various derivs of tetrazole(Ref 1) mw 474.43, N 32.46%; solid subst; was prepd
This compd forms a number of salts, some by Burrows et al(Ref 2) by the action of tri-
of which are expl: Barium salt, BaCd Nt2+2H20, ethyl lead acetate on the monosodium salt
orn-colored trysts, expl on heating; Di- of 1,3-b is(lH-tetrazo Iyl-5)-triazene. Due to
the fact that this compd can be ignited without
ammon%m
mp 275 ; expl ‘a Z*’ca
‘NH’‘8C’.N12
310 without ‘ed”vi?et
meltlng Crysts’
accord- detonation, requiring only 0.32 to 0.37 amps,
ing to Lifschitz & Donath(Ref 4); Potassium its use in ignition compns for electric blasting
“salt, K2C4N1 z, exists in yel & violet-colored caps was proposed by Burrows et al(Ref 2)
tryst forms, expl on heating; Silver salt,
Ag2C4Nl ~, violet trysts, expl ca 150°; 1,3-Bis(lH-tetrazolyl-5)-triazene,Ditriethyl
Sodium salt, Na2C4H12+2H20, exists in yel Lead Salt (called Bistriethyl-lead azoamino-
& violet tryst forms, both modifications expl tetrazole by Burrows et al),
on heating N-N[Pb(CH2 .CH3)3]-C.N:N.NH. ~-N[l%(CH2.-
Refs: l)Beil 26(201-202) 2) J. Lifschitz, Ber fi–– ; N
48,415-416(1915) 3)T.Curtius et al,Ber 48, CH3)3]–I#; mw 767.81, N 20.06%; trysts, mp
1619,1626,1631(1915) 4) J. Lifschitz & W.F. —----N
Donath,Rec 37,282-284(1918) 5) F. R. Benson, detonates ca 180°; was prepd by the action of
ChemRevs 41,6(1947) 2 mols triethyl lead acetate on 1 mol of the di-
sodium salt of 1,3-b is(lH-tetrazoly l-5)-triazene.
Bis(tetrazolyl)-triazene and Derivatives When gelatinized with nitrostarch, this compd
l,3-Bis(lH-tetrazolyl-5)-triazene or I,III-Di. reqd a firing current of 0.33-0.35 amps(Ref 2)
(tetrazolyl.5)-triazene{called 1.3-Di-[tetrazolyl Refs: l) Beil- not found 2) L. A. Burrows et al,
-(5)] -triazen or 5.5’-Diazoaminotetrazol in Ger], USP 2105635(1938) & CA 32,2357(1938)
~-NH-$ .N:N.NH.C-NH-N; mw 181.13, N
N— N %—fi N,N’-Bis(thiocarbamyl)-hydrazine (called
 B 159

Hydrazin-N.N’-bis-thiocarbonsaureamid; Di- Bis(triazo)-acetic Acid, Ethyl Ester. Same as

thio-hydrazod icarbonamid or “B is-thioharnstoff * Diazidoethylacetate, described under Ethyl
in Ger), H2N. CS. NH. NH. CS.NH2; mw 150.23, Acetate
N 37.30%; long prism s(from boiling w), mp
softens at 215°, dec ca 221-223°; sol in boil- Bis(triazo)-anthraquinone. Same as Diazido-
ing w; SI sol in cold w or ale; can be prepd anthraquinone, Ditriazoanthraquin one or
either by dehydrazination of thiosemicarbazide Anthraquinone Diazide, described under
or by condensation of thiosemicarbazide with Anthraquinone and Derivatives, Vol l,p A459- R
thiocyanic acid (Ref 2) and by various other
method s(Ref 1) Bis(triazo)-benzene. Same as Diazidobenzene,
This compd is an acid and forms salts with described under Azido and Azidonitro Deriva-
bases. It is a combustible material which tives of Benzene
flashes when dropped on a hot plate. Due to
its high nitrogen content and its compatibility l,2-Bistriazoethane. Same as 1,2-Diazidoethane
with NC, the compd has been proposed for
evaluation as a flash reducing agent in pro- Bis(triazo)-isopropanol. Same as Diazidoiso-
pellant powders(Ref 2) propanol
Refs: l)Beil 3,196,(79) & [136] 2)L. F.
Audrieth & E. S. Scott, “Compounds of High Bis(ß-sym or ß-l,2,4-triazole) or Bi(2H-l,2,4
Nitrogen Content” ,4th Quarterly Report,Univ -triazole) {called Di[l.2.4-triazoly l]-(3.3’) in
of IH(Oct 1951) Ger), ~H-N=~.-$=N-~H; mw 136.12, N
CH=N N=CH
Bistolyl. Same as Bitolyl
61.75%; CO1 lfts (from AcOH+concd HC1) or
ndls(from w), effls on exposure to air; mp un-
5,5’-Bis(p-tolyl)-1,1’-azotetrazole. See 1,1’
changed up to 300 ~ sublimes at higher temps
-Azo-5,5’-di(p-toly l)-tetrazole; Vol l,p A266-R
into prismatic trysts; sol in mineral acids or
alkalies; diffc sol in boiling w; insol in com-
Bis[5~(p*tolyl) *tetrazole~l]*diazene. See 1,1’
mon org SOIVS; was prepd by treating cyano-
-Azo-5,5’-di(p-toly I)-tetrazole; Vol l,P A266-R
hydrazine with boiling formic acid(Refs 1&
2) and by the method of Dedichen(Ref 3), who
Bis[5-(o-toly)-triazene. Same as Di(p-tolyl)-tri-
also prepd its salts. Tk Silver salt of bis -
azene
tetrazole can be cautiously sublimed with-
out decomp
Bis(l,3,5-triaza-3,5-dinitro-cyclohexylmethyl) Wiley & Hart(Ref 4) prepd 3,4’-Bis(l,2,4
-ether or Di(3, -5-din itro-l.,3,5. triazacycIobexyl- -triazole), large wh crysts(from hot w), mp
methyl)-ether{called 1, l’-(oxydim etbylene)-bis. 300-302 °(dec); sol in dil alk; obtd by slowly
[hexabydro-3, 5-dinitro-s-triazirze] in CA 5th heating 3-amino-I H-l ,2,4 -triazole and diformyk
Decennial Formula Index,p 383 F], hydrazine
Refs: l)Beil 26,601 2)E. L. Rinman,Ber 30,
02N.~ -cH2— N. CHZ.0.CH2.N-CH2 --N. N02; 1194(1897) & JCS 72 I, 444(1897) 3)G.
H2C-N(N02)-dH2 Hz&N(N02)-CH2 Dedichen,Avh andlNorskeVidenskaps-AkadOslo-
mw 396.29, N 35.35z; mono- Mat-NaturvKlasse 1936,N0 5,42pp & CA 31,
clinic crysts(from warm acet+chlf), mp begins 4986(1937) 4) R. H. Wiley & A. J. Hart,JOC 18,
to disintegrate at 129°; decomp extensively 1369(1953) & CA 48,12092(1954)
at 150°, forming a wh sublimate; was prepd by
the action of 100% HN03, at low temp, on 1 N,N’-Bis(s-triazol-3-yl)-formamidine or 3,3’
-methoxymethyl- or l-chloromethy I-3 ,5-dinitro -Bis(l H-1,2,4 -triazolyl)-form amidine,
-1,3,5 -triazacyclohexane and diluting the re- HC–N=$-N:CH.NH–$ =N-~H; mw 178.16, N
action mixt with eth. Its reaction with 96% fi-NH HN—N
HN03, acetic anhydride and acetyl nitrate 62.90%; wh rhombs, mp 285°; was prepd by
was reported(Ref 2) boiling for 2 hrs 2 mols of 3-amino-s-triazole
Refs: l) Beil- not found 2) K. W. Dunning & with an excess of over 1 mol of ethyl ortho-
W. J. Dunning,JCS ]950,2928-2931 & CA 45, formate, followed by cooling. This high-nitro-
6644(1951) gen compd was patented as a stabilizer for
 1

B 160

photographic emulsions. Its expl props were 4,4’-Bis(2,4,6-trinitrobenzeneazo)-azoxy-

not investigated benzene. See under Bis(benzeneazo)-azoxy -
Re/s: l) Beil- not found 2) J. D. Kendall & benzene
H. G. Suggate, USP 2534914(1950)& CA 45,
2350(1951) 3)Ibid,USP 2588538(1932) & l,2-Bis(trinitroethylamino)-benzene. See under
CA 46,4405-6(1952) Di(ethylamino)-benzene

Bis(triazo)-mesidine. See 2-Amino-4,6 -di- 1,4.Bis[N(2’,2’,2’-trinitroethyl)-carboxamide]

azido-mesitylene; Vol l,p A224-R to A225-L -piperazine, /CH2.CH,\
(02 N)3C.CH2–NH.CO–N N-CO. -
Bis(triazo)-phenanthrenequinone. Same as \CH2.CH<
Diazidophenanthre nequinone NH. CH2.CO(N02)3; mw 498.29, N 28.12; cal-
led N, N’~13is(2,2,2-trznit70 ethyl)- 1,4-p iperazine
Bis(triazo)-propanol, Same as Bisdiazidopro- Dicarboxamide and described in Conf DSRub.
panol ber Co Summary Report, Feb 1947,p 2

2,6-Bistriazo-4-trimethylammonium-l,4-benzo- N,N'-Bis(2,2,2-trinitroethyl)-ethylenediamine.
quinone. See 2,6-D iazido-4-trimethy lammonium See under Di(ethyl)-ethylene diamine
-l,4-benzoquinone under Benzoquinoneimine
and Derivatives N,N’-Bis(2,2,2-trinitroethyl)-ethyleneurea. See
under Di(ethyl)-e thyleneurea
Bis(triethyl)Lead Styphnate,
(02 N), C6H[OPb(CH2. CH3)3]2; mw 831.87, N N,N’-Bis(2,2,2-trinitroethyl)-hydroxylamine.
5.05%; yel trysts, mp expl 204°; was prepd See under Di(ethyl)-ethylenehy droxylamine
by Burrows et al(Ref 2) by reacting a dil alc
soln of triethyl acetate with an aq soln of Bis(2,2,2-trinitroethyl)-nitramine abbreviated
disodium styphnate at 600 as BTNEN and designated as HOX. Same as
It was proposed for use as an ignition compn Di(trinitroethy l)-nitramine, listed under Di-
in elec blasting caps ethyl amine
Refs: l) Beil- not found 2) L. A. Burrows et al,
USP 2105635(1938) & CA 32,2357(1938) N,N’-Bis(2,2,2-trinitroethyl)-piperazinedi-
carboxamide. See under N, N’-Di(ethyl)-pip er-
Bis(2,4,6-triisopropylbenzoyl)-furoxan, azinedicarboxamide
C~4H46N204. Its props and method of prepn
are given in Conf All L,”Synthesis and Test- Bis(2,2,2-trinitroethyl)-urea, abbreviated
ing of High Explosives”, 3rd Rpt(1953), p 384 as BTNEU. Same as Di(trinitroethy l)-urea,
and 4th Rpt(1956), p 57 listed under Diethylurea

Bis(2,4,6-trimethylbenzoyl)-furoxan, Bis(l,l,l-trinitro-isobutyl)-urea,
C22H22N204. Its props and method of prepn C2H5.$H.NH.C0.NH .$ H. C2H5; mw 442.26,
and its Bis(3,5*dinitro~ 2,4,6 *trimethylbenzoyl) C(N02)3 C(N02)3
-furoxan Derivative, C22H1 ~N601 z, are de- N 25.34%; an expl briefly described m conf
scribed in Conf ADL, “Synthesis and Testing of USRubber Co “Quarterly Progress Rept No
High Explosives”, ~rd Rpt( 1953),pp 376 & 378 14,Nord 10129, Feb 1,1951-May l,19Sl,p 6

1,2-Bis(2’,4’,6’-trinitronitranilino)-ethane. See
Bis(2,4,6-trimethylpyridino)-diazido-copper.
Same as Di(trimethylpyrid ino)-diazido-copper under Bis(anilino)-e thane

l,2-Bis(2’,4’,6’-trinitroanilino)-ethane. See l,3-Bis(2',4',6'trinitro-N-nitranilino)-propane.

under Bis(anilino)-ethane See under Bis(anilino)-propane

l,3-Bis(2’,4’,6’-trinitroanilino)-propane. See N,N’-Bis(l,l,l-trinitro-2-octyl)-adipamide,

under Bis(anilino)-prop ane C6H ,3.~H.NH.CO(CH2 )4. C0.NH.$H.CGH13;
C(N02)3 C(N02 )3

——
1
 B 161

mw 638.59, N 17.55%; described in conf US had been observed previously by Fichter &
Rubber Co Quarterly Progress Rept No 15, Jenny(Ref 1). Sax(Ref 10) discusses the toxic
Nerd 10129( May-Aug1951),p 7 nature and hazard of Bi and its salts. Vanino &
Menzel(Ref la) obtained, on reduction of basic
Bis(5,5,5-trinitro-2-pentanone)-cyanohydrazone. 13i nitrate with hydrogen, a black powdery
See under Di(2-pentanone)-cy anohydrazone material which oxidized spontaneously on
contact with air, even at RT. They called it
N,N’-Bis(2,4,6’-trinitrophenylamino)-ethane. pyrophomus bismuth.
See under Bis(anilino)-ethane Bismuth, as a metal, has been known since
the Middle Ages. It is found in ores as native
Bis(2,4,6-trinitrophenyl)-(a-amino-§.guanidino metal, as the sulfide, as oxide, as carbonate,
-valerianic acid). See Dipicrylarginine and as a minor constituent in lead, copper and
tin ores. The occurrence of bismuth in the
l,3-Bis(2’,4’,6’.trinitrophenylamino)-propane. crust of the earth has been estimated to be of
See under Bis(anilino)-propane the same order as silver & tungsten. The re-
covery of bismuth from various ores and by
4,4’-Bis(2,4,6-trinitrophenylazo)-azoxybenzene. various processes is discussed by Kirk &
See under Bis(benzene azo)-azoxybenzene Othmer(Ref 6)
Uses. Bismuth forms a number of alloys
Bis-N-(2’,4’,6’-trinitrophenyl)-l,2-dinitramino (principally low-melting alloys), inorg compds,
-ethane. See under Bis(anilino)-e thane org salts and coordination complexes. Bis-
muth and some of its compds have been used
N,N’-Bis(2,4,6-trinitrophenyl)-ethylenediamine. in medicine and for making pharmaceutical
Same as l,2-Bis(2’,4’,6’-trinitroanilino)-ethane products. Spaeth & William s(Ref 9) patented
described under Bis(anilino)-ethane a stable, gasless ignition or delay compn for
use in elec blasting caps, consisting of
N,N’-Bis(2,4,6-trinitrophenyl)-ethylene-di- bismuth 40-75, Se 25-60 and KCIOg 0.5-50%
nitramine. Same as Bitetryl, described under (all as 200-mesh powds). In 1943, Hart(Ref
Bis(anilino)-eth ane 5a) made a systematic study of inorganic exo-
thermic reactions in which the products would
1,2-Bis(2,4,6-trinitrophenyl)-ethyleneglycol be gasless and the compns might be suitable
Ether. See under Bis(phenyl)-ethy leneglycol as gasless powds for delay elements of fuzes.
Ether The possibility of using Bi with oxidizers,
such as AgzO, Ag2Cr 04, Ba 02, PbCr Oa,
N,N’-Bis(2,4,6-trinitrophenyl)-guanidine. See Cu20&Ba Cr04, was considered based on
under B is(phenyl)-guanid ine the calcd heats of reactions involved, ex-
pressed as kilo calories per equivalent wt.
N,N’-Bis(2,4,6-trinitrophenyl-nitramino)-ethane. However, many other metals were superior to
See under Bis(anilino)-ethane Bi in this respect, and Bi is not known to be
used in any US std delay compns for fuzes.
l,3-Bis(2’,4'’,6’-trinitrophenyl-nitramino)-pro- DeMent(Ref 10) patented the use of powdered
pane. See under Bis(anilino)-~ropane Bi in smoke-producing compns. Coenders(Ref
8) prepd a pyrophoric body by sintering and
Bismuth, Bi, at wt 209.00, reddish-wh metal, compacting a powd metal or alloy of a Iow-bp
mp 271°, bp 1436-1440°, d 9.78 at 20°, d(mol- metal, such as Hg, Zn, Mg, As, Sb or Bi, with
ten state) 10.07 at 271°, mean sp heat(O-270°) powd Ce or Ce alloy so as to produce surface
0.03cal/g, Qvap=n 42.7kcal/mol, thermal con- alloying (See also Bismuth Alloys)
ductivity 0.018caI/sec/sq cm/° C/cm; oxidizes Re/.s: l)F.Fichter & E. Jenny, Helv6,225(1923)
in moist air at RT; unites directly with halo- & CA 17,1599(1923) la) L. Vanino & A. Menzel,
gens & sulfur; H ~S04 converts it to Bi sulfat% ZAnorgChem 149,18-20(1925) & CA 20,684
HN03 reacts with Bi evolving N oxides. (1926) 2) Gmelin,Syst Nr 19,(1927),p 13ff
Nicholson & Reedy(Ref 4) reported the details 3)Mellor 9(1929),p 587ff 4)D.G.Nicholson &
in which violent explns can occur when metal- J. H. Reedy, TransIllStateAcadSci 27,78(1934);
lic Bi is heated with coned HC104. This fact CA 29,3517(1935) & JACS 57,817-18(1935)
 I

B 162

5)Thorpe 1(1937),694 5a)D.Hart,PATR 1239 of inorg compds, org salts and coordination
(1943) 6)Kirk & Othmer 2( 1948),526-30 complexes. Bi halides are formed by the
7)Partington(1950 ),872ff 8) A. Coenders,GerP action of halogens on the metal. The only well
811335(1951) & CA 47,7428(1953) 9)C.P. -defined oxide of Bfi is Bismuth Trioxide,
Spaeth & C. P. Williams, USP 2607672(1952) & Bi ~ O ~, rhmb yel trysts, mp 820°. It is used
CA 47,4084(1953) 10)Sax(1957),366 -67 to make some kinds of opticaI glass. It was
10a) J. DeMent,USP 2995526 (1961), P 7 also proposed for use in some smoke-producing
compns(Ref 7). Higher oxides of Bi are ppted
Bismuth Alloys. Bismuth is a component of a as reddish-brn powds on adding oxidg agents
number of low-melting alloys. Kirk & othmer to alkaline suspensions of Bi203 . According
(Ref 1) have listed eutectic alloys melting to Weingarten(Ref 8), Bi203 has been used by
below 200° and a few non-eutectic alloys the British in some delay compns, such as:
that are used extensively in industry Bi203 35, PbO 55 & Si 10%
Some common alloys include: Wood’s metal The most important Bi salt is Bismuth
(mp 710), contg Bi 4,Pb 2, Sn 1 & Cd I part; Nitrate, obtd as delq trysts, Bi(N03)3.5H20,
Rose’s metal(mp 93.8) contg ~i 2, Pb 1 & Sn by evapg a soln of the metal, oxide or basic
I part; and I-. ipowitz’ alloy(mp 60-5), contg carbonate in warm dil HN03. The soln, on
Bi 15, Pb 8, Sn 4 & Cd 3 parts. AI1OYS of Bi pouring into a large vol of w, deposits Basic
melting s-l above 100° are u sed in automatic Bismuth Nitrate, Bi(OH)2N03, used in medi-
sprinkling systems; less fusible alloys are used cine and formerly as a cosmetic and for the
as safety plugs in boilers(Ref 2). Bi alloys also prepn of other Bi compds. Anhyd Bi(N03)3
have important applications in industry for castings, cannot be obtd by heating the tryst salt,
other miscellaneous uses, and in certain types of as decompn occurs, but by drying in a vac
ammunition(Ref 1) over P20~ for a year. OZols (Ref 5) prepd
Bismuth.Manganese Alloy, developed at the Bismuthyl Nitrates, [( BiO)N03.H20], by
Naval Ordnance Laboratory, White Oak, Md, is slow diffusion of w into Bi(N09 )3 & HN03
a suitable substitute for permanent magnets: The toxicity and hazard of Bi compds is
Alnico or the expensive Pt-Co alloy. The Bi discussed in detail by Sax(Ref 6)
-bin alloy can be used in various electronic Re/s: l)GmelinSystNr 19(1927),106-13 &
device s(Ref 3). The Bi-Mn alloy known as 126-9 2)MeIlor 9(1929),643-59 & 705-11
“Bismanol”, prepd by powder metallurgy 3)Kirk & Othmer 2(1948),p 533-40 4)Part-
techniques, is claimed to possess a coercive ington(1950), p 873-77 5) J.Ozols, Latvijas-
force of 3000 oersteds(Ref 5) PSRZinatnuAkadVe stis 1950,N0 4,87-93 &
Bismuth-Sodium Solutions. G. P. Smith et aI CA 48,487(1954) 6)Sax(1957),pp 367-72
(Ref 4) detd the compn limits of reactions of 7)J.DeMent, USP 2995526 (1961),p 7 8)G.
air with solns of Na and Bi or Hg in the temp Weingarten, Pic Arsn; private communication
range 600-800°. For Na-Bi, the reaction was (1961)
accompanied by flame or a weak expln at
high temp and high Na concn. No reaction Bismuth Triazide. See Vol I,p A525-L
occurred at mole fraction of Na<O.45
Re/s: I)Kirk & Othmer 2(1948),P 531 Bisoflex 102. Brit designation for tri-
2) Partington(1950), p 873 3) Anon, Common ethyleneglycol dicaprylate, a solvent used in,
Defense Bulletin No 143(.Sept 1952), Washing- cast proplnts
ton, DC 4)G. P. Smith et al,JACS 77,4533 Re/: H. A. Aaron son. Dover, NJ; private communi-
(1955 & CA 49,15393(1955) 5)Cond Chem. cation (1960)
Dict(1961), 152-3
Bisulfate, Sodium(Niter Cake), A chemical in
Bismuth Azide. See Bismuth Triazide, Vol 1, the form of COI to It straw yel globules or
pA525-L granules contg a min of 30% H2S04. It is used
as a flux in dissolving minerals and in pickling
Bismuth Azidodithiocarbonate. See Vol l,p baths as a substitute for H2S04. Detailed re-
A636-R quirements of particle size and other props for
the material used by the US Army, Navy & Air
Bismuth Compounds. Bismuth forms a number Force are given in Military Specification
 B 163

MIL-S-16917A, Amendment 2,Feb 1956. Large CH3.C6H4.C6H4.CH3 , mw 182.25, H 7.74%.

quantities of this material were formerly obtd Several isomers of both sym and asym BitoIyI
as a by-product in the manuf of nitric acid are described in Beil 5,608-611,(286) & [512
from Chilean saltpeter(sodium nitrate): -5141
NaN03 + H2S04 = HN03 + NaHS04 Dinitro-bitolyl or Dinitro-dimethylbiphenyl,
CH3.C6H~(N02 ). C6H3(N02).CH3; mw 272.25,
Bitartrate(Acid Tartrate) of Potassium or N 10.29%. The 4,4’- 5,5’- G 6,6’- Dinitro-2,2’
Potassium Hydrogen Tartrate(Weinstein in .bitolyls (Ref 1); 4,4’- & 6,6’. Dirzitro-3,3’
Ger; Bitartrate de potassium in Fr), -bitolyls(Ref 2) and 2,2’- 2,3’-(?) & 3,3’.Di.
KHC4H406, mw 188.18, CO1 rhb trysts, d nitro-4,4’- bitolyls(Ref 3) are described in the
1.956; sol in w & SI sol in ale. Can be literature
obtained from argol(see Vol l,p A480) or by Re/s: l)BeiI 5,609 & [512] 2)BeiI 5,610,1& [513]
synthetic method s(Refs 1 & 2). Tavernier 3)Beil 5,61 O,61I & [514]
(Ref 5) detd some thermodynamic props of K Tetranitro-bitolyl,
bitartrate. Crude bitartrate, packed in bags CH~. C6H2(N02)2 .C6H2(N02)2.CH3; mw
called sachets antilueurs in French, has 362..25, N 15.47%. Only 4,6,4’,6’. tetranitro
been used as a flash-reducing compd in pro- -3,3’- bitolyl is described in the literature: It
pellants(Ref 3) -yel crysts(from AcOH), mp 234°; was prepd
Refs: l)Beil 3,494,(173) & [318-19] 2)Gmelin, by nitrating 3,3’-bitolyl with mixed acids(Ref
Syst Nr 22, Kalium(1938),957,1162 & 1222 2). TheiIacker & Baxmann(Ref 3) prepd the
3)Davis(1943),325-6 4)Kirk & Othmer 13 compd from 3 ,5-dinitro-o-chloroto luene, heated
(1954),648,652 & 655 5) P. Tavernier,MP 38, at 205-15°, by adding “Natur CU-C” (?) followed
293,294,297 & 331(1956) by heating and extracting the product with benz.
They obtd pale-yel crysts(from acet) melting at
Bitetryl. See 1,2-B is(2’,4’,6’-trinitro-nitraniline ) 198° and observed, prior to purification of the
-ethane under Bis(anilin o)-ethane and Deriva- compd, a remarkable color play(brown+ green+
tives red + yellow) depending on the pH, indicating
that traces of a compd,
Bithiophene and Derivatives H$-C(CH3)=C— C= C(CH3)-$H
Bithiopbene or Bitbierzyl[called Dithienyl-(2.2’ H2N.C–CH— L-N:N-L=cH —C.NH2,
or 3.3’) or a.a. or @.@j)-Dithienyl in Ger], were formed although it was not isolated. Its
C8H6S2, raw 166.27, Two isomers are described expl props were not detd
in Beil 19, 32,33 & [26] Theilacker & Baxmann(Ref 3,p 131) also
Dinitro-bitbiopbene, CsH~N204S2, not found attempted to prepare 5,6,5’, 6’-te trarzitro-2, 2’
in Beil or in CA thru 1956 -bitolyl by heating 3,4-d initro-o-chlorotoIuene
3,5,3’,5’-Tetranitro-2,2’.bithiophene [called with active Cu at 200°, but they were unsuc-
3,3’,5,5’-Tetranitro-2,2’-bithienyl in Ref 2 ] cessful
02 N. C—S—$ ~—S–$.NO, ; Re/s: l) Beil- not found 2) L. H.Bock et al,
H~ — C.N02 02N.C —CH JACS 52,2058(1930) & CA 24,3004-5(1930)
mw 346.27, N 16.18%; yel ndls(from AcOH), 3)W.Theilacker & F. Baxmann,Ann 581,126,131
mp softens at 181°j melts at 188-190°; upon (19531 & CA 48,12115(1954)
sublimation in vacuo at 200-210° and 3mm Hg, 2,4,6,2’,4’,6’-Hexanitro-3,3’-bitolyl or 2,4,6,-
the compd melted at .194.5 -196°; was prepd by 2’,4’,6’-Hexanitro-3,3’-dimethylbiphenyl,
heating 3 ,5-dinltro-2-chIorothiophene with Cu CH3.C6H(NOz)3 .C6H(N02)3.CH~; mw 452.25,
at 210-215° for 20 min(Ref 2). The UV absorp- N 18.58%; lt yel crysts(from AcOH), mp 240.1°;
tion spectra were detd by Jean & Nord(Ref 3). very sol in acet; so 1 in warm benz, toluene
Its expl props were not investigated or AcOH; practically insol in alc or eth; was
Refs: l)Beil- not found 2)G.N. Jean & F.F. prepd by condensation of 2,4,6 -trinitro-3-brom~
Nord,JOC 20,1368(195,5) & CA 50,9377(1956) toluene, in nitrobenz as a solvent, by means
3)G.N.Jean & F. F. Nord,JOC 20,1377(1955) of Cu heated at a temp not over 183°. Its expl
props were not investigated
Bitolyl and Derivatives Refs: l) Beil- not found 2)L.H.Bock et al,
Bitolyl or Dimethylbipbeny l(called Dimethyl JACS 52,2056(1930) & CA 24,3004-5(1930)
-diphenyl or DitoIyl in Ger),
 B 164

Bitumen. Naturally occurring, solid or semi- also exposed to light; mp becomes anhyd ca
solid, hydrocarbons including asphalt, mineral 110°, dec ca 190°; forms numerous salts, some
pitch, petroleum and naphtha. The ASTM desig- of which are unstable; other props and methods
nates them as the fraction of hydrocarbons of prepn are given in Ref 1
which are sol in CS2. They are rich in C and RochIin et al(Ref 2) detd the basicity con-
H and burn with a sooty flame stants of biuret and of a number of other org
Some bitumens have been used in coml expls nitrogen compds
and pyrotechnic compns as a coating for those Re/s: l)Beil 3,70,(33) &[60] 2) P. Rochlin et
ingredients which are either too hydroscopic al, JACS 76,1453(1954) & CA 49,3950(1955)
or too sensitive to impact or friction to be used 1. Nitrobiuret,02N .NH. C0.NH.C0.NHz; mw
uncoated. Izzo(Ref 5) lists the following ItaI 148.08, N 37.84%; wh tablets (from warm w),
pyro compns: a) Bitumen 10, hexachloroethane mp dec ca 165°, briskly foaming or exploding;
50 Z.n powd 30 & KN03 10% b)Bitumen 10, according to Davis & Blanch ard(Ref 2), the
hexachIoroethane 45, Zn powd 2S, KN03 15 & very pure compd dec at 233°; Q: 228kcal/mol;
ZnO 5% readily sol in warm w, alc or methanol; diffc
see also under Asphalt, Vol l,p A496-R sol in cold alc or w; decompd by boiling w
Re/.s: l)Davis(1943),p 35 2)Hackh’s(1944), into C02, N20 and urea; can be prepd by
p 132 4)Kirk & Othmer 2(1948),164 and 13 nitrating biuret in cold mixed HN03-HZS04
(1954),618 & 643 5)Izz0,PirOteChnia( 1950), It forms salts, some of which are expl, for
234 example, Silver salt, AgC2H3N404, wh ndls
from w by pptn with ale), expl on heating(Refs
Bituminite. of nongelatinous
A brand permis- 1&2)
sible explosives manufd by Hercules Powder Refs: l)Beil 3,126 & [100] 2) T. L. Davis &
Co, Wilmington, Del K. C. Blanchard,JACS 51,1803(1929) 3)S.Helf,
Ref: Bebie(1943),p 33 I. Minsky & B. Guide,PATR ]841( 1951) (conf,
not used as a source of info)
Biurea {called Hydrazin-N.N’-dic arbonsaure l,5-Dinitrobiuret, 02 N. NT-I. C0.NH.C0.NH.N02;
-diamid; Hydra zodicarbonamid; Hydrazo mw 193.08, N 36.28%; wh ndls(from MeOH), mp
-form amid; and Kohlensaure-amid-[ carbaminyl expl ca 124°; Q: 203 kcal/mol; very SOI in w
-hydrazid] in Ger], with a strong acid reaction; dec in boiling W;
HZ N. C0.NH.NH.C0.NH2; mw 118.10, N 47.4474 sol in ale, Me OH, acet or eth; insol in chlf,
crysts(from w), mp 246-266°; other props and Iigroin or benz ; can be prepd by adding, in
various methods of prepn are given in the lit- small portions, mononitrobiuret to well cooled
erature(Refs 1 & 2) 100% HN03 and evaporating the soln in dark-
It is compatible with NC, and the film prepd ness, in vacuo, over H2S04
from NC and biurea gave the following It forms salts, some of which are expl, for
stability(Ref 3): 90° C Vac StCZb Test, 2.99 example, Potassium salt, KzC2HN506, CO1
cc/5 g/40 hrs; 120° Heat Test, not acid in plate s(from lukewarm w), expl on heating
300+ hrs, no red fumes in 300+ hrs and no Refs: l)Beil 3,126 2) J. Thiele & E. Uhlfelder,
expln in 300+ hrs Ann 303, 95-99(1898) 3)S.Helf, I.hfinsky &
Refs: l)Beil 3,116-7,(56) & [95] 2)Inorg. B. Guide, PATR 1841( 1951) (Conf, not used as
Synth 4(1953),p 26-28 3) Picatinny Arsenal a source of info)
data(1955)
Bivinyl. Same as Butadiene
Biuret and Derivatives
B iuret, Allopbartamide; A llopbanic A cidamide; Bixylyl and Derivatives
Carbamylurea or Dicarbamylamine (called Bixylyl; Dixylyl or Tetramethyl-bip benyl(cal-
Kohlensaure-amid-ure id, Allophansaureamid, led Tetramethyl-diphenyl in Ger),
Ureido-formamid, Ammoniakdicarbon saure (CH3)2C6H3.C6HEI (CH, )2; mw 210.30, H 8.63%.
-diamid or Biuret in Ger),HzN.CO.NH. C0.NH2; The sym isomers 2,4,2’,4’-Tetramethy l-; 2,5,-
mw 103.08, N 40.77%; ndls+l mol H20(from w), 2’,5’-Tetramethy l-; 2,6,2’,6’-Tetramethy l-(Ref
loses part of its w of crystn on exposure to 2); and 3,4,3’,4’-Tetramethy l-biphenyl are de-
light; or anhyd Ifts(from ale), picks up moisture scribed in the literature
on exposure to humidity and more rapidly when Refs: l)Beil 5,620,(292,293) & [522] 2) J.Guy,

. .—
 B 165

JChimPhys 46,469(1949) & CA 44,4298(1950) Black Liquor. A by-product of paper manuf,

Dinitro-bixylyl or Dinitro. (tetrametbyI. bipbenyl), contg tar in addn to a small amt of aromatic
C1~H14N408, mw 390.30, N 14.36%. Two forrm hydrocarbons and phenolic compds. It was
of the isomer x,x, x,x- Tetranitro.3,4,3’,4’ - considered impracticable to use this tar, or
(tetrametbyl-bipbenyl) are described in the any fraction thereof, as a source of raw
literature: a)prismatic ndls(from dil acet), mp materials for expls
208-210°; and b)thin transparent ndls(from dil Re/: E.J. Hoffman, paper 23, No 19,11-13(1919)
acet), mp 267-8°. Both forms were obtd when & CA 13,515-6(1919)
finely powd nitrotetramethy ldiphenyl was grad-
ually added to fuming HNO~ and the soln Black Match. A slow-burning device used to
poured into w to ppt the product. The expl ignite black powder, or other expl train, and
props of the tetranitro-derivs were not inves- pyrotechnics. It can be made conveniently by
tigated twisting a few strands of cotton twine together,
Refs: “l)Beil 5,(193) 2) A. W. Crossley & C. dipping the cord into a paste of meal powd
Herbert, JCS 99 1,724-5(1911) and drying while the cord is stretched on a
Note: Higher nitrated derivs of bixylyl were frame. When black match is enclosed in a
not found in Beil or in CA thru 1956 paper tube, it burns almost instantaneously
and is then known as quick matcb. Black match
Biorkmann Explosives. C. G. Bjorkmann of may be ignited by a flame, whereas black
Stockholn invented in 1880 two expls compns: powder on a flat surface is often difficult to
a)KN03 20, KC103 20, “Cellulose ”(nitrated ignite
peas) 10, pea flour 10, sawdust 10 & “Nitro- Ref: Davis(1943), pp 4-5 & 67
Iine’’(nitrated mixt of stearin and sugar) 30%;
and b)(product of nitration of 3PS glycerin and BLACK POWDER OR GUNPOWDER
lp glucose) 60, Mn02 18, K ferrocyanide 10, (Schwarzpulver in Ger, Poudre noire in Fr,
Sb2S3 2 & pine sawdust or coal dust 10% Polvere nera in Ital, P61vora negra in Sp,
Re/: Daniel(1902),pp 72-3 Chornyi Pofokh in Rus and Yuenyaku or
Kokoshoku-yaku in Jap)
BKI. A cast double-base propellant developed Black powder, the oldest explosive and
at ABL. Its compn & props are described in propellant kndwn, consists of a mechanical
Conf ‘Propellant Manual”, SPIA/M2(195 9), mixt of saltpeter, charcoal and sulfur in pro-
Unit No 574 portions varying with the purpose. Here, salt-
peter is the oxygen producer, while charcoal
BKZ. A cast double-base propellant developed is the combustible material. Tk object of
at ABL. Its compn and props are described in sulfur is to make the powder readily inflam-
Conf “Propellant hianual”, SPIA/M2( 1959), mable and to form, on burning, K or Na sulfide
Unit No 504 (by reaction with K or Na nitrate) so as to
prevent part of the C02 from forming K or Na
BLA. A cast double-base propellant developed carbonate, which would, of course, mean a
at ABL. Its compn & props are described in reduction in the amt of gas evolved. Sulfur
Conf ‘Propellant Manual”, SPIA/M2(1959), also imparts the neeessary tenacity and density
Unit No 505 to the powder mass(Ref 34,p 191)
Historical (Refs 1,2,3,5,7,8,16,22 & 27). The
Black Diamond & Black Diamond Nu-Gel. A exact date of the discovery of BkPdr is un-
brand of nongelatinous US permissible explo- known. Some historians, such as Diego Ufano,
sives manufd by Illinois Powder Manufacturing attribute its discovery to the Chine se(in the
Co, St Louis, MO 1st century before Christ), others to the
Re/: Bebie(1943),p 33 Hindus and still others consider it of Arabian
origin. It is very probable, however, that
Black Dynamite. A mixt of powd coke and mixts similar to BkPdr were used very early
sand, impregnated with 45% by wt of NG by the Chine se(and perhaps by the Arabs) in
Re/s: l)Daniel(19tJ2),p 583 2)Clift & Fedoroff> the manuf of fireworks, rocket-type arrows or
Vol 4(1946),P 10 incendiary compns, but it was not used as a
propellant in firearms, as there is no proof
 1

B 166

that these were invented before the 13th of BkPdr, there is no proof for such a state-
century. According to Claudius, the Remans ment
were familiar with fireworks in the 4th century, .Accdg to Col Hime(Ref 2), the cannon was
AD and it was proved historically (Ref 16,p invented in 1313 by an “unknown” German
32) that as early as the 7th century, the monk and was introduced in 1314. It was used
Greeks had a secret mixt which possessed in the same year at the battle of Bangockburn
props similar to those of present BkPdr. The (Ref 8,p l)(See also under Cannon)
famous Greek Fire of Kalinikos contained It may be mentioned that the manuf of fire-
combustible material mixed with a substance arms and of BkPdr in Russia began about
closely resembling saltpeter in its props and 1389(Ref 15,p 255)
through its use many naval victories were won Notwithstanding the advantages of firearms
by the Greeks against the Arabs, Turks and (compared with the bow and arrow), it was not
Russians. The secret of the compn was well until the end of the 15th century that they be-
guarded for about 5 centuries after its inven- came prevalent in open warfare. By the begin-
tion, but the Turks finally obtained the formula ning of the 16th century the compn of BkPdr
and used the Greek Fire against the Christians was well stabilized, becoming very close to
at the time of the 5th Crusade(1217). During the formula used in modern times, namely,
the 6th Crusade (1249), the army of S aint saltpeter ca 75, charcoal 12.5-15 and sulfur
Louis was assailed in Egypt with incendiaries 10-12%. Although practically no changes have
thrown from ballistae, with fire tubes and been made in the compn since that time, many
with hand grenades of glass and metal, which improvements have been introduced which re-
scattered upon bursting(Ref 16; P 33). Marcus sulted in the prepn of more homogeneous mixts
Graecus, in about 800 AD, described in detail and in powders with better ballistic props.
the compn of the Greek Fire used in his time. The ballistics of firearms were also improved
It contained sulfur and saltpeter mixed with through mechanical design of the weapons
pitch and other combustibles. He also gives Until about the 17th century cannon balls
a compn of a BkPdr consisting of saltpeter, were solid pieces of either stone or iron(first
charcoal(willow or grapevine) and sulfur. introduced ca 1391) and BkPdr was used only
Marcus Graecus’ work was quoted by an for propelling these balls. When hollow cast
Arabian physician, Mesue, living in the 9th iron balls, provided with an opening and filled
century. Western Europe was in complete with BkPdr, were introduced, the powder be-
ignorance of such compnso It was sometime gan to function also as an explosive(bursting
before 1249 that Roger Bacon, a monk living charge). After loading a hollow ball with
in England( 1214-1292), described a mixt re- BkPdr, a time fuse(resembling the present
sembling the present BkPdr and, as far as is Bickford fuse) was inserted through the open-
known, this was the first publication on BkPdr ing in the ball. Then the gun was loaded
to appear in Western Europe. However, through the mouth with a propelling charge of
there was nothing in his writings to suggest BkPdr and after inserting the ball, the propel-
that he contemplated the use of BkPdr for ling charge was ignited through a hole near
propelling missiles or as an explosive the breech of the gun. The burning gases from
The invention of BkPdr did not revolutionize the decompn of the BkPdr ejected the ball
the technique of warfare in Western Europe and ignited the time fuse. After reaching the
because there were no firearms. This situation target, the fuse ignited the charge in the balI
lasted until about the beginning of the 14th which resulted in expln and bursting of the
century when Berth old Schwarz, a German ball into small pieces
monk living in Freiburg, described a device Another great improvement in firearms was
(an iron tube) for throwing stones a consider- the introduction in the middle of the 19th
able distance, using BkPdr as a propelling century of rifled barrels and then later of
medium. It is not certain whether this “fire- breech-loading. The first large-scale use of
arm” was the invention of Schwarz, or if he rifled firearms was during the Crimean War
only improved the already existing crude (1855-6) by the French, British and Italians
device. Although some historians, especially against the Russians, who still used smooth
German, attribute to Schwarz, not only the -bore firearms at that time
invention of firearms, but also the invention As the power, brisance and velocity of

, —-.--———
1
 B 167

detonation of BkPdr are low, firearms using it just before BkPdr ceased to be a war lord,
were neither powerful nor of long range the position it had occupied for nearly six
The ancient compns were in powder form centuries (from the Ist quarter of the 14th to
(from which the name “powder” is derived) the last quarter of the ~9th century). These
and they burned with extreme rapidity. To improvements included: a)the use of multiple
make them slower burning, the ‘Germ ans(ac- perforations in the prismatic grain by means
cording to some historians), as far back as of which the burning surface was made to in-
the middle of the 15th century, introduced crease as the burning progressed, resulting
grained BkPdr. According to other sources it in acceleration of the rate of gas production,
was in the Spanish Kingdom of Aragon that and b)the use of a slower burning formulation
the first grained BkPdr was produced. At first called Brown Powder or Cocoa Powder (also
the grains were irregular in shape and size, called Chocolate Powder), introduced by the
which lead to very non-uniform rate of burning. Germans in 1882( see below under Black
Gradually, it was learned that to obtain the Powder Modifications)
best baI1istics, the size and shape of the It is interesting to note that the first BkPdr
grain should be uniform. Napoleon was known factory established on the .Amer continent was
to have used roughly cubical grains 8mm in Mexico at the time of Herniin Cortez(16th
thick in the smaller field guns and grains century )(Ref 19). In the US, the first powders
about twice as thick in the larger guns. Later were manufd at Milton, Mass as early as 1675
solid prismatic hexagonaI grains of various and one year later were reported as being
sizes were introduced and in 1860 an Am- equal in quality to that of the best British
erican, Gen Rodman, deve Ioped (in an attempt powders
to make BkPdr progressive-burning) perforated In 1857, the only major change which has
cake powders which consisted of large, solid, been made in the compn of BkPdr was intro-
cylindrical grains(blocks) of nearly the same duced in the US by Lammot duPont, who sub-
diam as the bore of the cannon, contg a hole stituted the more abundant and cheaper sodium
about ~“ in diam along the axis of the cylinder. nitrate for the more costly potassium nitrate
One grain was required for each firing. This The following table gives the approximate
powder was sometimes called ‘tMammoth”. For compns of BkPdr from ancient times to the
larger cannon (such as 10 & 12-inch guns), the end of the 19th century:
blocks (prisms) were made in sections(discs)
which were joined by means of bands of paper
glued around the joint. When these single
K Nit-
rate IChar-
coal
sul-
fur

-perforated prisms were lighted, the area of China(before Christ) 72.6 I 19.0 8.4
the outer surfaces decreased as the burning Marcus Graecus(8th Cent) 57 ‘22 .1
advanced but the area of the inner surfaces Roger Bacon(ca 1252) 37.5 31.25 !1.25
increased and a high rate of gas production Ardeme Formula(ca 1350) 56.6 22.2 [1.2
was maintained. The Russians, Prussians Arabia(16th Cent) 74 ,15 .1
and the British soon adopted Rodman’s idea Brussels Formula 75.0 15.62 9.38
for their artillery. The perforated prisms were (Belgiumx1560)
manufd not only in large sizes, as advocated British Govt Formula(1635) 75.0 ,12.5 12.5
by Rodman, but also in small sizes, and such Swedish(1697) 73.0 17.0 10.0
powders, especially when used in rifled guns, American Co10nies(1775) 75.2 13.5 11.3
gave higher velocities and greater ranges British Watson Formula’ 75.0 15.0 10.0
than had been possible previously (EnglandX1781)
In 1862-1864, Doremus, in France, introduc- Military Powders in l?~opear 71-77 12.5-15 9-12.5
ed powders prpd by compressing the grains. States (I!%h Cent)
The conglomerate
granular structure
thus formed retained
but was slower burning
than grains in the loose form. This powder
the Blasting Powders in Europe
(19th Cent) I
52-73.5 12-19.4 1420

Sporting Powders in Europe 75-80 12-17 8-10

was used in small and medium caliber guns (19th Cent)
and proved to be satisfactory Powder in United States 75 15 10
The last two improvements in BkPdr were (19th Cent)
made in the 70’s and 80’s of the 19th century
 B 168

All of these improvements could not remove high of 277 million lbs in 1917 but has
two props of BkPdr which render it not very gradually declined since that time; pro-
desirable for use as a military propellant- low duction in 1947 was ca 36 million lbs
ballistic potential and production on firing of and in 1958 it dropped to ca 6 million lbs,
enormous amts of smoke, which quickly make of which 1% was used for blasting(Ref 33).
the location of artillery obvious to the enemy. In contrast to the figures on BkPdr, the pro-
Its low power, brisance and velocity of detona- duction of dynamite in the US(mostly NG
tion make it too weak for use as a bursting compns), used mainly in blasting operations,
chge for any but cast-iron shell is currently ca 1 billion lbs annually
With the invention, about the middle of the Black Powders Containing Potassium Nitrate.
19th century, of NG and NC, it beta me pos- The compn of most current military BkPdrs
sible to produce propellants practically is betw the following limits: K nitrate 74-78,
smokeless and of high ballistic potential. The charcoal 12-16 & sulfur 10-12.5%. Compns of
first ‘<smokeless” proplts(such as Austrian many sporting and blasting powders are betw
and British, developed betw 1864 & 1883)! the same limits. There are, however, some
were not colloided. Being porous, they burned exceptions, such as some Belgian blasting
very fast and often caused gun barrels to powders, which formerly consisted of KN03
burst. When the way was found to prep proplns 70-73.5, charcoal 12.5-14 & sulfur 14-16%
as non-porous grains- by gelatinizing NC, and a Russian blasting powder: KN03 66.6,
either with alcohol [see B Poudre (invented in charcoal 16.7 & sulfur 16.7%. One of the
1884 by P. Vieille) in this volume] or with a Russian sporting powders contained KN03
liq expl, such as NG see Ballistite(invented 80, charcoal 12 & sulfur 8%
in 1888 by A. Nobel), in this volume, the use Preparation (Refs 4, 16, 18 & 28). In earlier
of BkPdr and of Cocoa Powder as a military days, BkPdrs were prepd by grinding the
propInt was discontinued ingredients by hand in mortars. This was
With the discovery in the 1880’s that PA superseded by the socalled Stamp Mill,
(previously known for many years as an such as is briefly described in Refs 16,18 &
external medicine) is a very powerful and 28
brisant expl, combined with the introduction Modern methods of prepn consist essential-
by Turpin of new HE shell s(which were/es- ly of the following operations:
sentially the same as shells currently in use), a) Grinding, Mixing and Incorporating. Char-
the need of BkPdr as a bursting chge was coal(such as obtd by charring alder, willow or
completely eliminated. In later years, other poplar trees) is broken up by Wheel Mills and
HE’s were invented, such as Explosive D then pulverized after adding the required amt
(Ammonium Picrate), TNT, Tetryl, PETN, of sulfur (high grade, commercial product), in
RDX, etc a Ball Mill. In this operation sulfur is worked
AIthough BkPdrs are no longer used as into the cellular openings of the charcoal.
military proplnts or as bursting charges in The dampened material is mixed with K nitrate
shells or bombs, they-are still used as proplnts (previously finely ground) and the moisture
in some sporting weapons. They are also used content adjusted to ca 4%. About 300 lbs of
as blasting expls and for some other purposes this mixt are placed in a Wheel Mill(such as
(see below under Properties of Black Powders) described in Ref ll,p 46; Ref 18,p 69 or Ref
The use in Europe of BkPdr as a mining 28, p 87) where the mass is processed during
expl probably began in Saxony as early as 3-6hrs. This operation is called Incorporation
1613 and then in Hungary ca 1627. It was or Milling. The resulting material is called
used in England since ca 1670, slightly later “mill cake”, “clinker” or “wheel cake~. It
in Sweden, and in the American Colonies is broken into small pieces and sent to the
since ca 1712( Sims bury, Corm) press
With the growth of the steel and coal b) Pressing is done in hydraulic presses
industries in ‘the first half of the 19th where the material is subjected to a pressure
century, the use of BkPdr as a blasting expl of ca 6,000 psi. As the operation is dangerou~
increased tremendously until the production it is usually conducted by remote control. The
in the US in 1860 was ca 25 million Ibs cakes are broken up with wooden tools and
per year. production reached an all time transported to the Corning Mill

1 —..—
 B 169

c) Corning or Granulation consists of cracking rarely encountered together

up the cake into grains of desired sizes by Note: The opinion is held by some that the
means of a series of adjustable rolls having powder does not explode but merely de-
corrugated surfaces. The granulated material flagrates with the evoln of gases and it is
is then passed thro~gh a series of mechanical- these gases which finally explode
ly-shaken screens where the particles of dif- The main disadvantages of BkPdr are:
ferent sizes separate and the dust is removed. Weakness, production of )arge amt of smoke
The particles Are classified according to the and the corrosive action rh ‘metals of some
size of the kcreen and transferred to the of the products of its combustion. Alone, it
Finishing House. The coarse material is pas- is corrosive in the presence of moisture but
sed through the rolls a second time and re- not when dry
screened. The Corning Mill Dust is collected BkPdr is the slowest acting of all the com-
for use in fuses or in pyrotechnics. The Corn- mon expls. When used for blasting operations
ing operation is the most dangerous of all the it has a shearing and heaving action which
manufg operations and must be conducted by tends to break the material into large, firm
remote control fragments or masses. This action derives from
d) Finishing or Polishing is accomplished by a relatively slow development of gas pressure,
tumbling, for as long as 8 hrs, the granulated which is sustained. In order to obtain the best
material in a wooden drum, rotating on its results, it must be closely confined. BkPdr
axis. This operation may be combined with is unsuitable, however, for gassy and dusty
drying which can be accomplished by a stream coal mines because it produces a hot durable
of hot air. If a glazed powder is desired, a flame. Because of its high sensitivity to fric-
small amt of fine graphite is added to the tion, heat, spark and flame, danger of manuf
contents of the drum after the moisture has and inability to perform in many types of hard
been reduced to a certain point but before the -rock shooting, it has been replaced by other
powder is too dry. The moisture content of blasting expls(Ref 33)
the finished powder is ca 1% BkPdrs contg approx: KNOa 74-75, charcoal
Note: Final drying may be conducted by plac- 12.5-16 & sulfur 10-12 .5%(including the compn
ing the powder on trays covered with canvas KN03 74.0, charcoal 15.6 & sulfur 10.4%, de-
in the dry house scribed in Ref 31) may be considered to pos-
e) Grading of powder consists of rescreening sess(approximate ly) the following props(Refs
and separating into different ”grain sizes. The 11,16,20,28,31 & 34):
word “grade” applled “ to BkPdr refers to grain a)Brisance - by Kast formula B= 1.4 x 106 vs
size, not the quality 86 x 10s for TNT(Ref 11, p 95) by Sand Test-
f) Blending consists of mixing various grades 8g sand crushed by 0.40g BkPdr, vs 48g for
of powder to obtain a desired rate of burning TNT(Ref 31); 6.3 to 9.Og sand crushed(Ref 36)
or other props b)Calorimetric Value- ca 720cal/g(Ref 34)
Two processes for manufg BkPdr with c) Compatibility- in the dry state it does not
modern production equipment have been de- attack any of the common metals; attacks all
veloped and tested on a laboratory scale by of them, except stainless steel, when moisture
Propelled Chemical Division of Chromalloy is present(as low as 0.2% )(Ref 31)
Corp. Their final rept(Ref 35a) on the project d)Density - 1.7 to 1.89 depending on compn and
describes the two process es(one with and compression(Ref 28,p 87; Ref 31 and Ref 34
the other without the use of CS2), and also p 191
briefly discusses a number of other methods e).Equation o/ Combustion:
suggested by M.Baer and K. Kite of Pic Arsn Sukharevskii & Pershakov(Ref 9) give the
Properties: BkPdr is one of the weakest expls following equation:
and belongs to the class of “low expls” or 74KN03 + 16C6H20(Charcoal) + 32S = 56c02
“propellants”. It contains sufficient oxygen + 3CH4 i- 2HZS + 41i2 + 35N2 + 19 K2C03
for combustion to CO and nearly sufficient + 7K2S04 + 2K2S + 8K2S203 + 2KCNS + (NH4)s
for combn to C02. The outstanding character- C03 + 14C0 + c + 3s
istic of BkPdr is that it can be exploded(or Stettbacher(Ref ll,p 108) gives for powder
rather deflagrated) by ignition, yet it is very contg KN03 74.9, C 13.3 & S 11.8:
insensitive to impact, properties which are 2KN03 + 3C + S = K2S + 3COZ + N2
 I

B 170

Bofors Manual(Ref 34,p 190) gives the follow- produced by 10g sample vs 300cc for TNT
ing equation: (Ref 34,p 191); 10% of TNT(Ref 31); by Bal-
20KN03 + 32C + 8S = 5K2C03 + K2S04 + K2 listic Mortar 50% TNT(Ref 31); by Ballistic
S203 +3K2S + 2S + 11C02 + 16c0 + 10N2 Pendulum 42.5% of TNT for pdr contg KN03
of which about 43% are gases and ca 57% 75. o6, charcoal 13.68, S 10.76 & moisture
solid residues 0.50%(Ref 36)
In TM 9-1910(Ref 28,p 86) the following r)Rate o/ Burning, depends on compn, density
equation for autocombustion of BkPdr is given: and grain size. The rate increases on increas-
74KN03 + 96c + 30S + 16H2 = 35N2 + 14C0 ing the percentage of oxidizer(such as K or
+ 3CH4 + 2H2S + 4H2 + 19 K2COa + 7K2SOd Na nitrate), within certain limits. The rate
+ 8K#20~ + 2K2S + 2KSCN-+ (NH4)2C-03 decreases when the percentage of fuel(char-
+C+S+56C02 coal, coal, brown coal, etc) is increased. With
See also Ref 28a(discussion on ignition increase in the amt of sulfur, the rate increas-
and combustion reactions of BkPdr) and Ref es to a certain extent, although sulfur acts
28d (description of experimental investigation mainly as a fuel and only to a small extent
of the laws of combustion of BkPdr at atmos- as an oxidizer(because it forms K2S). The
pheric pressure and below) rate decreases with an increase in grain size
f)Explosion or ignition Temperature: 510° and sl decreases with increase in density.
(0.lsec; no cap used); 490° (lsec in cap); When confined, increase in gas pressure
427 °(ignites in 5sec); 356° (lOsec)(Ref 31): causes increase in burning rate(Ref 20,pp
359 °(12sec)(Ref 26a,p 1393); 457° (ignites in 37-8 & Ref 28b,pp 86-7). W. O. Snelling & W.
5sec)(Ref 36) C. Cope, USBurMines Tech Paper 6, Washing-
g) Flame Sensitivity- ignites very readily(Ref ton, DC(1912), give the rate of burning of fuse
20,p 37 & Ref 28,p 86): Escales(Ref l,p 394) pdr as influenced by temp, pressure, moisture
gives for prismatic pdr 5.4 to 9.0 sec and for and granulation. For instance, an 80-mesh pdr
small grain pdr 3.6 to 4.5sec burns at atm press and ord temp at the rate of
h) Friction Sensitivity by Pendulum Test- af- 82.3sec/m(25.l sec/ft) vs 76.3sec/m(23.2sec/
fected with steel shoe and unaffected with ft) for 40-60-mesh pdr. A cotton covered safety
fiber shoe(Ref 31); no expln with steel shoe fuse burns at atm press and 18° at the rate of
(Ref 36) 82.3sec/m(25.6sec/ft) vs 49.8(15.2) at 15psi
i)Heat of Combustion, Q; ca 1425cal/g(Ref 9) and 34.4(10.5) at 30psi(p 15). Moisture & high
j) Heat o{ Explosion, Q: 665 to 690cal/g(Ref temps cause a decrease in burning rate. Safety
9); 693cal/g(Ref 36) fuses mfd by the DuPont Co burn either 90 or
k) Hygroscopicity gains 1.91% at 25° & 90% 120sec/yd(Ref 28, p 89). Some fast-burning
RH(Ref 31) fuse pdrs burn ca 30sec/yd, whereas some
l)lgnitability, flame of a match or of a miner’s modified slow-burning pdrs, such as those
squib as well as electric spark ignites it(Ref contg aldol-a-naphthy lamine and aldol-~-naph-
36) thylamine, burn at the rate of 250-300 sec/yd[H.
m) Impact Sensitivity: Pic ArsnApp, 2kg wt 16” H. Holmes & W. E. Lawson,USP 2414465(1947)
(VS 14” for TNT) (Ref 31); Bofors Detn, 2kg & CA 41,2578(1947)]. Escales(Ref l,p 396)
wt ca 70 cm(Ref 34, p 191); B of M, 2kg wt gave for a rifle BkPdr at latm press 0.80cn/
49cm for KN03 BkPdr and 66cm for NaN03 sec & at 500atm 6cm/see; the corresponding
BkPdr(Ref 36) values for a brown prismatic pdr were 0.90
Deck(Ref 6) gives 32” for BkPdr dust & 4cm/sec. US Army Purchase Description
when detd by PicArsnApp with 2kg wt X-P A-P D-623 gives “static burning time~
n)lnitiation and thermai decomposition of requirements for fuze pdrs when tested
BkPdr is discussed by Blackwood & Bowden directly in fuzes. For instance, for fuzes M54,
(Ref 28a) M55A3, M77 or M84 the average burning time
o)lnternational Heat Test at 75° - 0.31% loss shall be 18.0 to 23. Osec and the “minimum
in 48 hrs(Ref 31) average burning time” 36. Osec. The correspond-
p)hlaxifium Temperature of Explosion- 2380° ing values for M65A1 fuze are 9.0 to 13. Osec
vs 2800° for TN T(Ref 11, p 95); ca 2400 °(Ref & 18. Osec. Tests for “rates of burning” of
34,p 19) black blasting pdr and for pellet pdr are de-
q) Power, by Trauzl Test- 30CC expansion scribed by C. E. Munroe & J. E. Tiffany, Bur-

. ...————-..—
 B 171

Mines Bull 346, “Physical Testing of Explo- For a description of various grades of
sives”, Govt PrtgOff,Washington, DC(1923). US military BkPdrs and their uses, see JAN
Combustion of BkPdr at atm and Iower -P-223A
pressures was studied by A, Douillet,MP 37, The compns listed above may be considered
167-96(1955) as /ast-burrzing, while the following compn is
s)Serzsitivity to Electrostatic Discharge slow-burning: K nitrate 59.0, charcoal 15.6,
(Joules) >12.5 for unconfined and 0.8 for con- sulfur 10.4 & Ba nitrate 15.0%. By blending
fined sample(Ref 31) fast- with slow-burning mixts in different
t) Sensitivity to Flame. See Flame Sensitivity propns, it is possible to obtain powders
u)Sensitivity to Sparks and incandescent Par- suitabIe for various types of fuzes
ticies- very sensitive(Ref 28,p 88) Another slow-burning mixt is the so-caIled
v)Speci/ic Energy(f) 2310 vs 8080 for TNT Coal Powder. Its compn is: K nitrate 70.0~1.0,
(Ref 11) Seal 14. Otl.O & sulfur 16. Otl.0%. The US
w)Speci/ic Heat ca 0.2cal/g at RT(Ref 36) Armed Forces requirements for this powder
x) Vacuum Stability - 0.5ml/40hrs/100° and are given in Spec X-PA -P D-623 (listed as Type
0.9ml/40 hrs/120° (Ref 31); 0.86ml/40 hrs/ II Powder, Black, SIow Burning) which super-
120° for black meal powder and 0.75 for meal seded Spec JAN-P-540. The coal used for
pdr contg 2% stearic acid(Ref 36) this powder must be semibituminous and of
y) Velocity of Detonation- ca 400m/sec at d such fineness that 100% passes through No
1.6-1.7 vs 6825 for pressed and 6640 for cast 140 US Std sieve and hot less than 45%
TNT at d 1.56(Ref 31); 400m/sec at 1.7(Ref through No 200 sieve. Other requirements for
34,p 191) coal are: moist 0.75% (max), ash 11.0~1.5,
z) Volume o{ Combustion Gases at 0° & 760mm v~latile matter 18. Otl, fixed carbon 70.5t3.5
271-280 J/kg vs 690-730 for TNT; ca 280 l/kg & sulfur 3. OtO.5%; no foreign matter, such as
(Ref ll,P 95 & Ref 34,p 191) gritty or fibrous particles, shall be present.
z ) Uses: Sporting proplnts, blasting and dem- This BkPdr shall be of such fineness that
olition expls, time fuses, primers, igniters(of 3%(max) is retained on a No 140 US Std sieve
smokeless proplnts), time rings(in fuzes), and 2%(max) retained on a No 200sieve. Static
delay & relay elements, petards, pyrotechnics, burning time, when loaded in US Std Fuzes
base chge for shrapnel shell s(now seldom M54, hf55A3, M77, M84 and M65A1, must be
used), bursting chge for blank, saluting & as indicated above under Rate o{ Burning(iterrJ
practice cartridges & shells, flash reducer r). No gritty or fibrous matter shall be present
(in some smokeless proplnts), squib charges, A BkPdr used in US time {uzes for military
Navy donuts for catapult charges, smoke-puff ammo consists of K nitrate 74. Otl.0, charcoal
chges, chemical ammo as well as in Rocket, 15.6~1. o & sulfur 10.4tl .0% and the require-
JATO and missile boosters and sustainers ments of the US Armed Forces are covered
(Ref 28b,p 86; Ref 31 & Ref 34) by Spec X-P A-PD-623 (listed as Type 8,
Black Powders, Containing Potassium Nitrate, Powder, Fuze), which superseded Spec
Used in the United States of America. Re- JAN,P-TRP. The ash content 0.60%(max)
quirements for the US Armed Forces are and granulation must be of such fineness that
covered by the Specification JAN-P-223A for 3%(max) is retained on a No 140 US Std sieve
:he powder alone; JAN-P-156 for potassium and 2%(max) passes through a No 200 sieve.
titrate; JAN-C-178A(1) for charcoal(usually When loaded in US Std Fuze M54, hf55A3, M77,
>btd by burning peeled willow, alder or certain M84 and M65AI the static burning time of the
~ardwoods); JAN-S-487 for sulfur and JAN-G powder musr be as indicared above under Rate
,155(1) for graphite. Tk compn is the same of Burning (item r); no gritty or fibrous matter
‘or all grades: K nitrate 74.0, charcoal 15.6 shaIl be present
k sulfur 10.4%, but tolerances vary slightly BkPdrs for blasting operns by the DuPont
‘up to t 1.0%). The ash content for all grades Co are described in Ref 27,pp 45-8. Their
.s 0.80 Y.(max), moisture 0.70% for all grades Pellet Powder may be considered as an im-
~xcept A-1, for which the max is 0.50%, and proved form of BkPdr
he density is 1.72 to 1.77. No foreign matter
;uch as gritty or fibrous particles shall be Black Powders, Containing Potassium Nitrate,
>resent Used in Eurapean Countries. BkPdrs used in
 B172

Europe have practically the same formulations in the adjacent cake. These cakes were easily
as those used in the US. As an example, the broken, however, in the course of transporta-
following compns of powders were used in tion and were soon replaced by prismatic pow-
France before WW II(Ref 12,p 280) der(see below)
K nit- * sul- d)Prismatic Powder was made in the form of
rate coal ~ hexagonal prisms, ca 1.25” wide and 1“ deep,
—. —
with a hole through the center 0.4” in diam.
Poudre de Guerre 75 12.5 12.5 The prisms were packed to form rigid cartridges
(Military powder) for use in guns of large caliber (See also Refs
Poudre de mine forte 75 15 10 14,15, 17,22,23,30 & 31a)
(Strong mining expl) Black Powders Containing Sodium Nitrate.
Poudre de mine ordinaire 62 18 20 These powders, introduced in 1857 in the US
(ordinary mining expl) by Lammot duPont, are less expensive than
Poudre de mine lente 40 30 30 the KN03 compns but are more hydroscopic,
(Slow mining expl) much slower and slightly weaker(Ref 27)
Poudre de chasse* 78 12 10 Requirements for the US Armed Forces are
(Sporting powder) covered by Specification JAN-P-362(1) for
poudre de guerre brun 78 19 3 the powder itself; JAN-S-322 for sodium
(Brown military powder) nitrate; JAN-C-178A(1) for charcoal; JAN-S
*P. Tavern ier, MP 36,232(1954) gives for black -487 for sulfur and JAN-G-155(1) for graphite
sporting powder: KN03 75-78, charcoal 12-15 Composition of the powder: Na nitrate 72.0
&S 9-12% t2.0, charcoal 16.0t2, sulfur 12.0t2.0, ash(in
eluding deterrent if used) 1.5 & moisture (max)
0.70%, density 1.72-1.84. It is glazed with
As there is no info at our disposal on current graphite. There are three classes, according
British BkPdrs, we are using here the descrip- to granulation: a) Class A- 100% through NO 12
tion given in Thorpe(Ref 13a, p 584). The pow- sieve, 45% through No 16 and 99% retained
ders used in England were classified accord- on No 40; intended to be used for saluting
ing to the size of grain. Some of them describ. chges, usually in the form of pellets b)Class
ed below are definitely obsolete Et. 99% retained on No 16 sieve; intended for
a) Grain Powders were prepd by passing ir- use in practice bombs c) Class C- 100% through
regularly broken pieces of pressed cake a sieve opening of 9/16” and 100,70 retained on
through a series of rolls, each set of rolls a sieve opening of 3/8 ; intended for use in
causing a progressive reduction in the size torpedo impulse charges
of the grains. In the case of small arms pow- Sodium nitrate BkPdrs used in mining and
der, the grains were first reduced to pass to some extent in demolition work are usually
through No 10 BritStd sieve and were then in the form of cylindrical pellets ca 2“ long
screened on a No 20 sieve to remove fines and ranging from 1 1/8” to 2 1/2 in diam. The
and dust. The sized grains were then polished pellets have a 3/8” hole in the center which
and coated with graphite and AI powder facilitates rapid and uniform ignition and
b) PebbZe Powders were manufd first ca 1865. permits a fuse to be inserted into or through
The press-cake was cut into uniformly sized the pellet. This opening will also seat an
cubes ranging from 5/8” to 1.5” on a side. electric squib. The pellets are wrapped in
These powders were larger than ordinary paper to form cartridges of any desired length
grain powders and were used in order to (usually 8“) and the cartridges are dipped in
prevent the development of excessive pres- paraffin, or similar material, to protect the
sures. They are now obsolete powder from moisture. Pellets are more con-
c) Per/orated Cake Powder, devised in the venient and less dangerous to handle than
US by Rodman ca 1860, was made in the other forms of BkPdr(Ref 27)
form of cylindrical cakes which were pierced Pepin Lehalleur(Ref 12, p 287) and Sancho
axially with ca ~“ holes. The cakes were of (Ref 15,pp 285-6) give compns of some European
the same diam as the bore of the gun in which powders contg Na nitrate, such as:
they were used and were packed in cartridges
with the holes in one cake aligned with those See Chart Next Page

———.
 B 173

Lowering of the burning rate may be achiev-

De Tret’s Freiberg & Soulagt
ed by one of the foIIowing methods:
Composition Pyronome W’etzlar’s Powder
a)Addn of inert bodies, such as brick dust,
graphite, Ba or Pb sulfate, oxides of various
Na nitrate 71.3 61.7 -66.7 50-60
metals. Fuses contg these substances do not
Charcoal 15 17.4 12-16
burn very uniformly and they leave large
Sulfur 13.5 11.8 -17.2 13-6
. residues
soot . 9-18
b)Addn of rosin. This method increases the
Oak Bark - 18.7 -
. time of burning from 45 sec per yard to 900
Iron Sulfate - 4-5
sec
Moisture - 2.8 -
. c)Treatment of the grains of powder with a
soln of NC(or other cellulose product). This
Black Powder Modifications. treatment not only modifies the rate of burn-
A modification of BkPdr, known as Brown-, ing but also renders the powder less hydro-
Cocoa-, or Chocolate Powder (s o named be- scopic
cause of its brownish color) was invented in d)Substitution of pitch for charcoal may in-
Germany ca 1882. It contained K nitrate 79, crease the time of burning from 45 to 180 see/
brown charcoal(contg ca 2% H20) 18 & sulfur yd and even to 500 sec(method of Foster &
2% and was made in the form ~f prisms. The White)
brown charcoal was prepd by incompletely e)Introduction of triphenyl phosphate, camphor,
charring a light wood or straw and hence substituted ureas, etc, suggested by F. Olsen
contained more volatiles than black charcoal. f)Substitution of cuprene, wholly or in part for
The compn of Brown Pdr was kept secret until charcoal
the Russians published in 1886 the formulation One of the most recent modifications of
of their own powder manufd at the Ochra plant, BkPdr is the so-called Benite developed at
near St Petersburg. The Russian powder con- PicArsn by Hassmann(Ref 33a) for use in
sisted of K nitrate 78.4, brown charcoal 19.6 igniter compns of artillery primers or in base
(prepd from incompletely charred rye straw) igniter bags for separate-loading ammo. This
and sulfur 2.0%. As the partially charred wood powder is, accdg to Huselton & Kaplowitz(Ref
or straw possesses some colIoidaI props, it 35), in the form of extruded strands consisting
enabled the compn to flow under pressure, thus of the ingredients of BkPdr(KNO~, charcoal
cementing the grains together, as in the case & S) in a matrix of NC. The ratio of BkPdr in-
of sulfur. This made possible a reduction in gredients to NC is 60/40
the amt of sulfur or even its complete elimina- Benite can be manufd by a SOIV extrusion
tion, thus making the powders slow-burning. process, using essentially the same mixi~g,
The use of Brown Pdr greatly improved the extrusion & drying facilities employed in the
ballistics of big guns and made possible the manuf of double and triple base cannon proplnts.
use of larger caliber guns than could be used Based on production engrg studies to improve
with BkPdr. AIso, for equal muzzle velocities. the manufg process, Huselton & Kaplowitz(Ref
Brown Pdr produced less pressures than BkPdr(Ref 35) developed an acceptable spec which was
13a). Brown Pdr was also used by the US Armed practical for production use. Some requirements
Forces, as late as 1898, during Spanish-American in the R & D Spec PA-P D-1741, such as
war moisture content, total volatiles, & the use
A modification of BkPdr which does not com
of reagent gd KN03 were changed. The re-
tain sulfur is called sulfurless bIack powder,
sulting changes are contd in the current spec,
A sample of such pdr manufd by the King
MIL-B-45451, 27 Jan 1960
Powder Co was examined at PicArsn in 1941.
Both the friction pendulum and deton hazard
The pdr contained KN03 ca 70 & charcoal 30$Z
(SOIV wet) tests show that Benite reacts sim-
Its d was 1.63(Ref 36)
ilarly to single base, ~f-18 proplnt and there-
A BkPdr used in safety fuses must consist
fore may be considered a Class 2 expl hazard
of fine, uniformly grained partic Ies free from
when wet. The functioning characteristics of
dust. This type of powder must be of special
of benite are relatively unaffected by minor
quality and constant compn, contg, in some
changes in dimensions of the strands and
cases, various additives for controlling the
formulation (Ref 35)
rate of burning
 B 174

Details of the manufg procedure for std and 230 A,33-46(1955) CA 49,1520 -l(1955)(In-
modified Benite formulations are given by hibition of burning of BkPdr by foreign sub-
Huselton & Kaplowitz(Ref 35). Hassmann stances) 28d)A.Douillet MP 37,167-96(1955)
(Ref 33a) reported physical, chemical and sen- 28e)W.Y. Carmen, ”A History of Firearm s”, St
sitivity characteristics of stci 13enite in com- Martin’s Press, NY(1955),l-11 & 157-62
parison with those of Grade A-1 BkPdr. The 29) Gorst(1957),156-9 30)Yaremenko &
std Benite formulation, as given in the specs, Svetlov(1957),l 10-12 31)Tomlinson &
is as follows: NC(13.15%N) 40, K nitrate 44.3, Sheffield,PATR 1740, Rev 1(1958 ),32-6
sulfur 6.3 & charcoal 9.47. with EtCentr 0,5% 31a) Fedoroff et al,PATR 2510( 1958),p Ger
added 173-R 32) Taylor & Gay(1958),18-21 (Use of
Other modifications of BkPdrs are listed BkPdr in blasting) 33) Cook(1958),8
after Refs 33a)H.Hassmann, PicArsn FREL,Propulsion
Refs: l)R. Escales, C’SchwarzpuIver und Development Section Report No l(1958)(Conf)
Sprengsalpeter’’, Veil & Co, Leipzig(1910) (Not used as a source of info) 33b)C.Campbell
2)H. W. L. Hime,’’The Origin of Artillery ”, Long. & G .Weingarten, TrFaradSoc 55 2221-8(1959)
mans-Green, London(1915 ),28,60,95 & 149-69 33c)Ibid,PicArsnMonograph M43(1959)(Thermo-
3)Marshall 1(1917),53-91 4) J. A. Marshall, analytical study of ignition & combustion)
“The Manufacture and Testing of Military Ex- 34) A. B. Bofors Nobelkrut, ”Manual on Powder
plosives”,McGraw-Hill, NY(1920),l14-17 and- Explosive s”, Bofors,Swe3en(1960 ),190-1
5) Van Gelder & Schlatter(1927),3 ff(History of 34a) J. R. Partington, c’A History of Greek F ire
BkPdr in the US) 6)H. S. Deck, ArmyOrd 7,34 and Gunpowder, He ffer, Cambridge, England(1960)
(1926 )( Impact test value for BkPdr dust) 35) E. Huselton & S. Kaplowitz,P icArsnAmmo-
7)H. Desvergnes,ArmyOrd 10,191-4(1929) Group, TR DB-TR 5*60( 1961) [Evaluation Tests
(History of development of military powders) and Process Studies Relating to Establish-
8)hfarsha113( 1932),l-5 9)Sukharevskii & ment of Substitute for Black Powder(Improve-
Pershakov( 1932),169 10)Vennin, Burlot & ment in Manufacture 6f Benite Strands)]
L6corch6 (1932),505-24 ll)Stettbacher( 1933), 35a) Chromalloy Corp, DAI-23-072-501-ORD(P)
3, 95 & 97-113 llaM-V-Lapchenkov .’’Kurs -43, Final Rept, July 1,1961 36)Wm.H.
DymnykhPorokhov” ,GoskhimTekhIzd at, Moscow Rinkenbach,A llentown, Pa; private communica-
(1933) (in Rus) 12) Pepin Lehalleur( 1935),279 tion(1961)
-89 13) Beyling-Drekopf (1936), 1 & 67-71 List of Modifications of Black Powder
13a)Thorpe 4(1940),458 14)N.A.Shilling,’’Kurs The following compns, which appear to rep-
Dymnykh Porokhov”,Oboronguiz, Moscow(1940) resent the most interesting developments, are
(in Rus) 15) Sancho(1941 ),253-86 16)Davis listed in chronological order:
(1943),28-51 17)M.M.Kostevitch,’’ Espoletas A)J.P.Gray,USP 1438759(1922) & CA 17,882
de Tiempo y P61vora Negra para Ios Reguladores (1923 )( Rosin 2-12% is added to BkPdr as re-
Inferior y Superior”, Buenos Aires(1943) tarder) B) Lignosa S. Akcyjna, FrP 641442
17a)’W.Has senstein,SS 39,1-9, 22-6 & 37-42 (1927) & CA 23,1272 (1929 )( Charcoal in BkPdr
(1944) (The Chinese and the Discovery of is replaced by hydrocarbons such as C , OH* sulfo
Powder) 18) Anon, “Ammunition Inspection acids of C ,0H8 or phenols, nitrosulfo acids of phe-
Guide”, TM ~*1904(1944),68-79 19)P~rez nols, nitrosulfo acids of phenols. Carbohy-
Ara(1945),133-48 20) AII&EnExpl( 1946),36-9 drates, such as cellulose, starch or sawdust
21)Stettbacher( 1948),l,20 & 58-9 22)Vivas, also may be used) C) Dynamit A-G, PhrNaoiim
Feigenspan & Ladreda 3(1948),3-74 23)Giua, & A. HOlz,GerP 499402(1929) & CA 24,4160
Dizionario 2(149 ),162-4 24) J. Fauveau,MP 33, (1930) (Powdered petroleum coke is used to
452(1951) (Evolution of propellants) 25)Kirk replace charcoal) D)R.L.Hill,USP 1833573
& Othmer 6(1951 ),3-7 & 77(under Explosives) (1931) & CA 26,1125 (1932 )(Mixt of ?3kPdr with
26)H.Henkin & R. McGill,IEC 44 Y1393(1952) an O-carrying salt, such as AN or NH4C104
& CA 46,8857(1952) 27)Stettbacher( 1952), coated with graphite, rosin or paraffin)
78-80 28) Blasters’ Hdb(1952),45-8 & 89 E)J.A.Hammond,CanP 311894(1931) & USP
28a) J. D. Blackwood & F. P. Bowden, PrRoySoc 1872941(1932); CA 25,3838(1931) & 26,6141
213A,285-306(1952) & CA 46,10623(1952) (1932)(A slow-burning & free-pouring expl is
28b)Anon,’’Military Explosive s’’, TM 9s1910 obtained by treating BkPdr with asphaltum di~
(1955),86-91 28c)S. Bentur et al, PrRoySoc solved in CS2 & drying) F) R. L. Hill,USP

.————,
___
I
 I 75

1845663(1932) & CA 26,2320 (1932 )(Mixt of Q) A. J. Clear, PicArsnChemLabRept 99983(1943)

BkPdr with AN coated with a combustible (BkPdr substitute contg KN03 40, Tetranitro-
material deficient in O, such as TNT, NC carbazole 30 & aluminum pdr 30% was prepd
or a carbohydrate) G)R. L. HilI,USP 1845664 and examined at PicArsn) R)R.C.Payn et al,
(1932) & CA 26,2320( 1932) (Mixt of BkPdr with BritP 576107(1946) & CA 42(1949)(A compn
a O-carrying salt, such as AN or Nli4 C104 suitable for delay combustion trains by addn
coated with S & charcoal) H) W. A. McIntre, to BkPdrs of an aldehyde-amine condensation
CanP326148(1932)& USP 1882853(1932); CA product) S)O.Matter,SwissP 244352(1946) &
26,6140(1932) & 2~,846(1933)(Rate of burning CA 43,4468 (1949)(A BkPdr substitute contg
of BkPdr consisting of NaN03, S & charcoal carbonaceous material prepd by extg coal
is decreased by incorporating ca 0.5% of a with high-boiling org solvents, such as a coal
water-emulsifiable oil, such as sulfonated oil) -tar oil, followed by filtration and removal of
I) B. A. GiIlie,CanP 324731(1932) & USP the solvent from the filtrate by distn)
1927870(1933); CA 26,5422(1932) & 27,5981 T)W.H. Rinkenbach & V. C. Allison,USP 2415848
(1933)(A slow-burning BkPdr suitable for (1947) & CA 41 ,2900( 1947) (Slow-burning BkPdr
fuses is obtained by incorporating ca 0.5% of suitable for fuses is prepd by replacing char-
high-viscosity oil, such as castor oil) J)C.W. coal with non-cellular C obtd by decompn of
Brooks,CanP 348641(1935) & CA 29,3518(1935) sugar. For instance, the fuse contg:KN03 74,
(Addn of 0.1-0.5% of stearic acid retards the S 10.4 & sugar C 15.6% burns about 3.3 times
rate of burning; eg, NaN03 72.0, S 10.0, char- slower than the pdr contg charcoal) U)H.H.
coal 17.7 & stearic acid 0.3%) K)C. W. Brooks, Holmes & W. E. Lawson,USP 2414465(1947) &
Jr,USP 2030096(1936) & CA 30,2388(1936) CA 41,2578 (1947)(A faster-burning BkPdr
(Stability of BkPdrs contg AN is improved by suitable for fuses may be obtd by replacing
incorporating 0.2% or more of a solid org basic charcoal by a special type of C black produced
compd such as urea of dicyandiamide) by incomplete combn of natural gas or other
L)C.W. Brooks & C. R. Johnson,CanP 377516 gaseous fuel. For inst, the compn KN03 74,
(1938) & CA 33,2339( 1939)(Addn of 0.2-2% of S 9.5 & C black 16.5% burns 46 sec/yd vs
a non-fibrous binding agent, such as starch, 75 sees for pdr contg charcoal) V) R. C.Payn
in prepn of BkPdr pellets) M)H. H. Holmes, et al,USP 2423427(1947) & CA 4],6050(1947)
CanP 384570(1939) & CA 34,1488 (1940 )( Pellets (Slow-burning fuse pdr, such as 250-300
of a de flagrating expl consisting of BkPdr, AN sec/yd, is prepd by incorporating 2 parts of a
(15-45%) and at least one finely divided com- mixt of aldol-a-naphthy lamine & aldol-~-naph-
bustible metal, such as Al) N) J. Simon & D. thylamine into BkPdr contg KN03 75, alder
Hewitt,USP 2179434(1939) & CA 34,1488(1940) charcoal 17 & S 8%) VI )S. Living ston, PATR
(Mixt of BkPdr with a product obtained by 1647( 1947) (Conf)(Development of non-hygro-
nitration with HN03 + H2S04 of an incompletely scopic igniter powder) W)M.de Simo,USP
charred ceIlulose) O) R. Healy, Astronautics 2566602(1951) & CA 46,1767 (1952)(A BkPdr
No 53, 3-10(1942) & CA 39,5077 (1945 )( Various -type expl obtd by combining KNO~ with sulfo-
BkPdr compns used in rockets are discussed) hydrocarbons and/or sulfoc arbons in lieu of
P)D. Hart”Investigation of Use of Nitroindene carbon and S. Details of prepn are given)
Polymer in Powder for M54Time Fuze”, P.4TR W, )S. Livingston,PATR 1802( 1951)( Conf)(A
1296(1943). [Substitution of nitroindene poly- BkPdr substitute for use in artillery ammo)
ner for charcoal, yielded longer burning fuze X)F.P.Bowden & J. D. Blackwood,BritP 715827
>owders and lowered the ignition temp, while (1954) & CA 49,2736 (1955 )( Sulfur-free BkPdr
t considerably increased the sensitivity to is obtd by addg to KN03 + charcoal about
mpact. Compns of two pdrs examined at Pic- 10-15% of an alkali metal salt of formic acid)
!rsn were: a)KN03 74.0, nitroindene polymer X1) Ibid, BritP 715828(1954) & CA 49,2736
15.6 & sulfur 10.4% and b)KN03 67.8, nitro- (1955 )( The reaction rate of BkPdr may be
ndine polymer 20.4 & sulfur 9.8%. The impact increased as much as ten-fold by addg low
sensitivity of both pdrs was 20cm with 2kg wt, -melting mixts of alkali metal nitrates, such
,S 75cm for BkPdr contg KN03 74.0, charcoal as LiN03 + N.aN03) Y)Ibid, BritP 715829
.5.6 & sulfur 10.4%. Because of their high (1954) & CA 49,2736 (1955 )( The reaction rate
sensitivity to impact, the nitroindene polymer of BkPdr may be increased by addg small amts
~drs were not recommended for use in fuzes] (eg 5%) of a metallic saIt such as PbOAc,
 1

B 176

which will react with H2S as it is Iiberated in two-stopcock bulb with 100-g sample is used.
early sta ges of burning) Z) H. Hassmann, In both cases, mercury is used for displacing
PATR 2515( 1957)( Conf)(Eimite, a substitute the air
for BkPdr in artillery primers) C, Granulation is detd by separating the
product under std conditions using a series
Black Powder, Analytical Procedures: of sieves of different sizes. The app is de-
I) Qualitative Tests scribed in Bofors manual(Ref 10, P 23). A
A. Appearance- visual inspection of the similar method is used in the US(Ref 2,p 66
uniformity of pdr and color of the grain s(Ref and Federal Spec RR-S-366)
lo,p 191) D. Moisture. In the Bofors’ method(Ref 10,pp
B. Identification. Place ca 0.2g of material 15 & 191) a 5g sample is dried in an oven at 75° for
in a 5-ml beaker, add 2-3 mI distd w an”d stir !lhrs. In the BM method(Ref 2,p 69) a 2-g sample is
for 5 min. Decant the Iiq through a filter into spread on a 3“ watch glass and dried over coned
a small beaker, Evap this to dryness and H2S04 in a desiccator at RT for 3 days. This
test part of the deposit(white, in the case of method is described in US Specs (Refs 11,12
BkPdr) with 1 drop of 1% DPhA soln in coned & 13) as an alternate to the method in which
H2S04, using a white porcelain spot-test plate a 2-g sample is dried on a watch glass (or in
A blue color indicates the presence of a a dish) for 4 hrs in an oven at 70°
nitrate. Place another portion of the deposit in E. Composition. This usually includes sulfur,
an indenture of a white porcelain spot-test charcoal and K or hla nitrates. In the Bofors’
plate, add an equal amt of tryst thymol and Method(Ref 11 ,p 191), a previously dried 10-g
3 drops of coned H2S04 . Stir the mixt and note sample of BkPdr is extracted with CS2 for
the color in 5 reins or more. A green color in- 16 hrs in a Soxhlet app. After removing the
dicates the presence of a nitrate. Heat the thimble, the SOIV in the flask is distilled off
w-insol residue in the 5-ml beaker to dryness, and the residue is dtied at 70°. This gives
cool and digest with two 5-ml portions of CS2 sulfur content. ,After drying the thimble, its
decanting these into an evapg dish. Evap to contents are transferred quantitatively to a
dryness at RT and examine the deposit(yel, previously dried and tared sintered glass
sulfur, if the sample is BkPdt) by means of a crucible of medium porosity (such as Jena
microscope. Examine also the residue after CS2 1G3 or Pyrex h4), in which it is treated with
treatment(black, carbon, if the sample is Bk hot distd w until the nitrate reaction of the
Pdr)(Ref 9,pp 269-73) wash w had disappeared. After drying the
II. Quantitative Tests crucible at 100° to const wt, it is cooled in
A. Bulk Density, also called gravirrzetric a desiccator and weighed. This gives char-
density or apparent speci~ic gravity, is the coal content. The nitrate content is obtained
relation betw wt and VOI of the pdr. This by difference 100%-(% sulfur + %charcoal)
includes the air spaces betw grains. In the In the US method(Ref 2,pp 70-72 & Refs 11,
Bofors method, Ref 10,p 23, a cylindrical 12 & 13), the following procedure is used:
vessel of 100ml capacity is filled through a A)K or Na Nitrate. Transfer a known wt of a
special funnel and then weighed without sample(ca 10g) to a 400-ml beaker, add 200ml
shaking. In the BurMines method(Ref 2,p 67), distd w, bring to a boil and hold for 15 min
the so-called gravimetric method is used. US on a steam bath. Filter through a sintered
Army Specs(Refs 11 & 12) do not describe the glass crucible and wash with successive
bulk test portions, 10-15 ml, of hot w until the nitrate
B. Specific Gravity, also called absolute reaction(blue coloration when tested with
density, is the relation betw wt and volume DPhA in coned H2S04 ) of the wash w has
of grains disregarding the air spaces. The disappeared. Dry the crucible to const wt
Bofors manual(Ref 10, p 22) describes two at 70°(ca 4 hrs), cool in a desiccator and
methods: Mohr-Westphal’s balance and pycno- weigh. Calculate the percentage of nitrate
meter methods. In the Burh4ines method(Ref on a moist-free basis
2,p 67), an apparatus called densimeter is B)Sul/ur. Place the crucible and contents
used. In US Spec JAN-P -223 A(Ref 11) two from the previous operation in an extractor
methods are described in which either a on a water bath and extract for 4 hrs with
25-ml bottle with a 10-g sample or a large CS2. Wash the residue in crucible once with

— —. . —.— ..—
 B 177

alc and once with ether using suction. Dry 3K2S203 + 8KMn04 + H20 . 6K2S04 + 8Mn02
for 1 hr at 100°, COOI in a desiccator and + 2KOH
weigh. Calculate the percentage of S on a Add 25ml HCl(dl.19) to dissolve Mn02, filter
moisture-free basis. This operation removes and heat the filtrate to boiling. Add 25m I of
only rhombic sulfur. If the presence of a- boiling 10% BaC12 soln and leave the liq
morphous S is suspected, the residue must be overnight. Det the amt of Ba S04 by the usual
washed, after CS2 extraction, with several method and talc the % of sulfur
portions of hot aniline followed by alc & ether Saltpeter is detd by boiling 2g BkPdr with w,
washes filtering and weighing the dry residue. Here
C) Charcoal. If the pdr is not graphited, the the wt of residue is C+ S and the loss in wt
residue in the crucible after detn of KN03 and the saltpeter
S may be considered as charcoal. Det its Charcoal is calcd by subtracting the amt of
weight by subtracting the original wt of the detd S from wt of residue
filtering crucible from the wt of crucible + Refs: l)R. Escales, “Schwa rzpulver und
residue. Then talc the wt of the residue Sprengsalpeter”, Veit, Leipzig(1914); physical
as percentage of charcoal on a moisture-free tests, 381-89; chemical tests, 389-91; bal-
basis listic tests, 391-405 2)W. O. Snelling & C.G.
Note: Slow-burning pdr(Type II, in Ref 13) Storm,’’ The Analysis of Black Powder and
contains coal in lieu of charcoal Dynamite”, BurMines Bull 51 ,Washington,DC
D) Foreign Matter. Examine the residue in the (1916); physical examination 66-8; chemical
crucible for foreign matter such as fibers, examination, 69-76 2a) I. V. Lapchenkov, ”Kurs
sticks, stones, sand etc. No such matter shall DymnykhPorokhov,’’G osKhimTekhIzdat, Mos-
be present cow(1933)(in Rus) 3) V. Ohman & G. Laurent,
E) Ash. Ignite the crucible with charcoal in ZAnalChem107,409 -11(1936) & CA 31,2007
a muffle furnace or over a Bunsen Burner until (1937 )(Detn of saltpeter in BkPdr using a
all the carbon is burned off. Calculate the Zeiss interferometer) 4) A. A. Azzam, Mikro-
wt of residue as percent ash chimAkta 2,283-6(1937) & CA 32,1933(1938)
The US Specs requirements(Refs 11,12 & (FeigI’s spot tests used in analysis of BkPdr
13) for various types of BkPdrs are listed combustion products) 5) A. W. Baker, Explosives -
above under Black Powder Engr’’l~,l l5-l7(l939) & CA 33,5661 (1939)(A
Lapchenkov(Ref 2a,pp 59-60) describes the method for detg the burning rate of BkPdr by
following method of Bkpdr analysis: using an open steel pipe) 6)A.Wetterholn,SS
Sulfur can be detd by two methods: 38,189-92(1943) & CA 38,4131 (1944 )(Detn of
a)Boil in a tall 11 beaker lg of finely divided moisture in BkPdr) 7)Kast-Metz( 1944),5 -19
BkPdr with 100ml HN03(d 1.4), adding period- 8)H.Henkirr & R. McGill,IEC 44,1391-5(1952)
ically small amts of dry KCIOa and new por- & CA 46,8857 (1952 )(Expl temp of BkPdr detd
tions of HN03 . Continue boiling until complete in a speciaI apparatus) 8a) A. DouilIet & P.
dissolution of sample and the color of liq Miaud,MP 36,277-84(1954) & CA 50,3764(1956)
becomes light yel. Dilute the soln with ca (Studies of ignition and burning of BkPdr in a
6 volumes of w, heat to boiling and add 25ml manometric bomb) 9)Anon,’’Military Explosives”
of boiling 10% BaC12 soln. After leaving the Dept of the Army Tech Manual TM 9*1910(1955),
Iiq overnight, det the amt of BaS04 by the 90-1 & 273 IO)AB Bofors,Nobelkrut,’’Ana-
usual method and”calc the % of sulfur lyrical hlethods for Powders and Explosives”,
b) Place in a 200ml beaker 0.3g of finely di- Bofors,Sweden( 1960), 191 I1)US Spec JAN-P
vided BkPdr, add 25ml of 3% NaOH soln, -223 A,’’Powder, Black” 12)US Spec JAN-P
cover with a watch glass and boil for 45 -362, “Powder, Black, Sodium Nitrate” 13)US
reins. The following reaction takes place: Purchase Description X-PA-PD-623, “Powder,
4S + 6K0H + 2K2S + K2S20a + 3H20 Fuze” and “Powder, Black, Slow Burning”
Add 25ml of 3% KMn04 soln & few pieces of Black Powder Destruction. If the powder is in
unglazed porcelain or pumice stone and boil containers(25- or 50-lb drums), they must be
for ca 40 reins. The following reactions take opened with wooden or non-sparking metal
place: tools and if a stream or large body of water
3K2S + 8KMn04 + 4H20 + 3K2S04 + 8Mn02 is at hand, the pdr can be dumped into it. (For
+ 8KOH detailed instruction see SR 75-7@ 10/AFR 68-3)
 I

B 178

The w will dissolve saltpeter leaving sulfur at/or near such an operation shall be limited
and charcoal as deposits, both of which are to 100 lb. If a fire should take place during
harmless. The washings must be disposed of these operations, one must immediately with-
separately from the residue. This method can- draw to a safe distance because of danger of
not be used in places where anti-pollution expln. Every effort must be made to prevent
laws exist. In this case, the pdr must be sent the fire from spreading to a BkPdr magazine.
to the burning ground (qv) to be destroyed in If this, however, fails, firemen should be
the following manner: withdrawn to at least 800ft from the magazine
a)open one of the containers, using a wooden and either stand behind a barricade or lie
or non-sparking metal tool, and spread the flat on the ground. If an expln of a BkPdr
contents on the ground in a trail(strip) not magazine should occur, all efforts of firemen
wider than 2“ and not over 1-2” deep, in such must be concentrated in preventing spreading
a manner that no part of the trail parallels of fire to adjacent bldgs, especially magazines
another part within a distance of 10 ft. The with expls & ammo
ground over which the trail is laid should be Refs: l)”Safety and Storage Manual for Ex-
free of cracks or other depressions in which plosives and Ammunition”, 00 Form 5994,Secn
the pdr might accumulate and be in some X1(1928) 2)TM 9.1904 (1944),p 78-9
confinement Black Powder Packing, Storage, Handling,
b) Lay a train of combustible material(such as Safety Precautions, Maintenance, Inspection
paper or excelsior), preferably on the down- & Surveillance, Shipping and Transportation,
-wind side of the trail, of such a Iength(ca 2S A std container for packing & shipping BkPdr
ft) that the operator can reach a safe place is a commercial iron drum(25-lb capacity)
after igniting the paper. Ignite the combustible complying with ICC specifications. BkPdr
material may also be packed for storage in 50-lb metal-
c) After the pdr burns, wait until the ground lic containers or ,in 110 lb metal lined smoke-
cools before starting the destruction of the less proplnt boxes, but the amt in each con-
2nd and subsequent containers. If space per- tainer must be limited to 50 lb. The containers
mits use a new area of ground for 2nd, etc, must be stored in bullet-proof magazines used
containers. Never burn more than one con- for storing expls and ammo, but never in
tainer(25 or 50 lb) at a time barracks, general supply rooms, inhabited
d)Wash out the empty containers with w bldgs or any bldgs heated by stoves or open
Refs: I) Anon, “Safety and Storage Manual for fires. Instruction for proper piling(stacking)
Explosives and Ammunition”, 00 Form 5994, the containers in a magazine are g’iven in Ref
Seen XI, US Army, Chief of Ordnance, Wash- 2,p 790. Max amt of BkPdr allowed in one
ington,DC(1928), p 3 2) Anon, &Ammunition In- magazine is 250,000 lb
spection Guide”, TM 9.1904 (1944),pp 773-4 As BkPdr is very sensitive to sparks, fric-
3)R.D. Leitch & P. R. Moyer,US BurMines,Inf- tion and heat, strict sa/ety precautions must
Circ 7335( 1945 ),pp 3-4 4) Anon, “Ordnance be exercised in handling it. In a bldg contg
Safety Manual”, Ordnance Corps Manual ORDM BkPdr, only safety (non-sparking) shoes must
7-224(1951) 5)Anon, C’}iilitary Explosives”, be worn and all tools and equipment must be
Dept of the Army Tech Manual TM 90191 O(1955) of non-sparking materials, No work around
315-17 G) Anon, “Care, Handling, Preservation BkPdr shall be done other than that involving
and Destruction of Ammunition”, Dept of the the storage and handling of containers or
Army Tech Manual TM 9-1903(1956),179 powders. If a storage magazine has a concrete
Black Powder Fires. BkPdr can be ignited floor, it must be covered with a tarpaulin or
easily by sparks, heat or friction. When uncon- other suitable material. If it is necessary to
fined, it burns with expl violence but will transfer the pdr from one container to another
expl if ignited under even slight confinement. conductive rubber mats must be used at lo-
Only safety tools(such as made of wood or of cations where such operations -are performed
non-sparking metal) shall be used when open- (Ref 4,p 80)
ing or closing containers. This will be done Note: According to Ref 3,p 79, ”A container
onIy in a bldg free from other expls & ammo will not be opened in a magazine in which
or, in suitable weather, in the open at least expls or ammo are stored. This wilI be done
100 ft from the nearest magazine. The quantity only in a room or bldg free from all other

*
 B 179

expls or ammo, or in suitable weather in the ‘Washington, DC(1928),Secn XI 2) Anon,’’Am.

open at least 100 ft from the nearest m agazine” munition Inspection Guide”, War Dept Manual
To this may be added that if repacking is con- TM 9*1904 (1944),77-8 & 79o 2a) An’on,’COrd.
ducted outside, it is advisable to do it under nance Safety Manual”, ORD M7*224(1951),
a very light cover, such as canvas 14-11 & 20-4 3)Anon,’’Military Explosives”,
Loose BkPdr is especially sensitive and Dept of the Army Tech Madual TM 90191Cl
whenever it is necessary to handle it, not (1955),306 & 311-14 4)Anon, ”Care,Handling,
over 50 lb of such pdr in open containers and Preservation, and Destruction of Ammunition”,
not over 50 lb in closed containers (total 100 Dept of the Army Tech Manual TM 9*1903(1956),
lb) must be permitted at or near such opera- 80 & 146 5)Sax(1957),Section II 6) B. Kanouse
tions &C. V. Ruskewicz, PicArsn; private communica-
If BkF’dr is spilled on benches or floors, all tion (1961)
work in the vicinity must be stopped until the
pdr has been removed and the expl hazard of Blainite. An Italian mining expl utiIizing dis-
any remaining dust or fine particles has been carded military propellants. It consisted of
removed by washing down the area with w Ballistite or Cordite (previously pulverized)
Most of the above operations belong to 60, AN 25, NaN03 10, Pb(N03)2 3 and
maintenance activities. To these may be Ba(N03)2 2%
added repainting & marking of containers, Re/: Molina(1930),362
replacement of metallic caps, etc
Since BkPdr deteriorates with the absorp- Blake Explosive, proposed in 1865 for filling
tion of moisture and the containers in which grenades and torpedoes; consisted of K
it is stored are subject to rust, a thorough chlorate and sulfur. It was the predecessor of
inspection of these articles must be made at Sprenge~ Explosives, known as Cbeddites or
least once a year. For this, one or several Street Explosives
containers from each lot will be opened at the Re/: Stettbacher(1933 ),309
time, of annual inspection and if there is any
doubt about serviceability of the pdr, it must Blanche Dynamite (White Dynamite). An old
be removed to the lab for physical and chem- Austrian dynamite, as invented by M. Diner,
ical testing. At the same time, the containers consisted of NG 70, guhr contg limestone 19.35
must be inspected for holes, weak spots, etc. & woodpulp 10.65%
Damaged containers should not be repaired Re/: Daniel (1902),73
but removed and the contents transferred to
new containers. All of these operations may Blanche Dynamite de Paulilles. An old expl
be called surveillance similar to Dynamite No 1 and contg NG 70-75
Rooms or bldgs in which BkPdr is handled & siliceous earth 30-25%
must be frequently examined for the presence Re/: DanieI(1902),73
of BkPdr dust and all such dust must be im-
mediately removed with w Blanche Poudre. Fr for White Powder. See B
All containers with powder intended for (Poudre)
Shipment must be previously inspected and
those going overseas must be crated Blank Ammunition. See under Ammunition and
Transportation of BkPdr within the USA is Weapons or Arms, IIA(According to Service
governed by “Regulations for the Transporta- Use), Vol l,p A383-R
tion of Explosives and Other Dangerous
Articles by Freight” established by ICC Blank Cartridge is a cartridge charged with a
(Freight Tariff No 8). BkPdr is shipped as blank powder(qv)
“Class A“ expls which include those mat-
erials representing an expln hazard in case Blank Cracker is a pyrotechnic device with
of fire but not in case of an accident with- an expl chge and fuze designed to serve as a
out fire(Ref 3,pp 311-14 & Ref 5) dummy weapon for simulating a live weapon
Refs: I) Anon,’’Safety and Storage Manual such as a hand grenade. It should explode with
for Explosives and Ammunition”, 00 Form a loud crack without any danger to personnel
No 5994, US Army Chief of Ordnance, or surrounding objects. One type of such blank
 I

B 180

-crackers was recent Iy patented in England area, whereas bomb fragments do damage only
Ref: K. Hjellnes(Oslo, Norway), BritP 726302 at random points of impact
(1955) & CA (1955-60)-not found When a bomb ~pe HE(such as TNT, Comp B,
HBX or Torpex) detonates, the solid chge is
Blanketed(Cased or Enveloped) Explosives. rapidIy converted into gaseous products. This
Same as Sheathed Explosives process, occurring in approx 0.0001 sec developes
very high temps & pressures. These values vary
Blanketing Compositions for Blasting Explo- with the them compn of the expl but their order
sives. See under Sheathed Explosives of magnitude is 100,000 atms (700 tons/sq in)
press and 3000” ( 5400”F) temp. Of the total
Blank Powder is used in firing signals, for energy available from the expl, as much as ~
saluting, for manoeuvres and, in fact, in all may be used to expand the casing (bomb body)
cases where it is required to make noise of and the remainder is used to compress the
firing without ejecting a projectile. Instead of surrounding environment. This latter energy is
projectiles felt wads are used. As the wads responsible for the blast effects
do not offer resistance to the expansion of Prior to WWII Trau71 Lead Block Tests (See
pdr gases, the pressure in the weapon decreas- VolI,pXXV) were made on the expl itself and
es after firing almost to zero. In order to offer bombs were detonated in an enclosure te deter-
greater resistance to the pdr ga ses the cart- mine the number and penetrating Power of the
ridge is sometimes provided with a ~~mock bomb fragments. Although both tests give
shot” made of hollow wood or other suitable valuable info, neither i = directly related to the
material which breaks up at the muzzle of the blast effectiveness of an expl. Quantitative
gun. The pdr used in blank firing should be blast measurement techniques were deveIoped
rapid-burning. The desired rate of burning in England in 1938 and later in the USA at
may be achieved either by using partially Aberdeen Proving Ground (APG) (Refs 4 & 12,
gelatinized materials, similar to those used p 86) and Princeton Univ in 1941 &’1942(Ref 13).
in bulk sporting proplnts(See Bulk and Con- (See brief description of blast measurement
densed Powders) or by using finely divided methods under Blast Meters)
completely gelatinized smokeless proplnts. Many investigators have made experimental
One of the most common smokeless blank studies of the blast from bombs and from bare
proplnts. is EC Blank Fire Powder (qv). It charges (Refs 2,7,9,11& 26). Theoretical
has been used in cal .30” blank ammunition discussions of the formation of the blast waves
BkPdr is still used in some types of blank have been reported by Kirkwood & Brinkley
ammo (Ref 5), Cole(Ref 10), Taylor(Ref 14), Berry etal
Re/s: l)Marshall 1(1917 ),334-5 2)Ohart(1946) (Ref 18) and others (Refs 12, p 58ff; 21 & 22)
30 3) Anon, nMilitary Explosives”, Technical Blast Effects in Air (Air Blast E//ects). When
Manual TM 9*191 O(1955), 249 an expl charge is’ detonated in air, the gaseous
products expand rapidly and compress the sur-
Blast. A phenomenon caused by a rapid expan- rounding air so that it moves outward with high
sion, at high pressure and temperature, of velocity, thus initiating a shock wave. ,~is
the gases resulting from an explosion(see layer of compressed air is bounded by an ex-
Blast Effects) tremely sharp front, called the shock /rorzt, in
which the pressure rises abruptly. The shock
front moves outward with an initial velocity
BLAST EFFECTS IN AIR, EARTH AND WATER much greater than that of sound but, after a
(Air Blast Effects, Blast Energy. Blast short distance, the velocity decreases rapidly.
Impulse and Blast Pressure)(the latter is The gaseous products of deton move as a
called Detonations-d-. -k in Ger) strong wind behind the shock front and are pre-
h military operations it is a known fact, vented by their own inertia from decreasing as
proved during WWH, that greater damage can rapidly as the pressure at the point of deton. As
be done to installations by blast effects from a result, there is produced a rare~actiorz e~~ect
bombs than by metal fragments from bombs or and a point of reduced pressure, which condit-
other conventional projectiles. Blast waves act ion trails the shock front. When the pressure
as a severe earthquake and cover a circular becomes less than atmospheric, the wind rever-

—.
1
 IMPULSE , OR POSITIVE IMPULSE
= AVERAGE PRESSURE X DURATION
P . AREA UNDER TRUE EXCESS PRESSURE
FOR OURATION OF POSITIVE PHASE

I
I
I
I TIME, THOUSANDS OF A SECOND
I I I I I I
o 5 10 15 20 25

TYPICAL PRESSURE-TIME RECORD FOR THE BLAST FROM A BOMB

ses in direction and blows back toward the and light wt, with respect to the area presented
point of deton. The shock front, the high press to the shock f[ont, require high peak press but
area behind it and the trailing rarefaction con- no great impulse; while heavy but relatively
dition, form a complete wave which is called weak structures require considerable impulse
blast or shock wave but not such a high peak press to cause demo-
In expressing the blast effect of an expl, it lition, For example, window glass requires a
is necessary to describe both peak pressure moderately high peak press but only a low im-
and impulse: pulse value; while a brick wall withstands only
a small peak press if the impulse value is high
In the above fig of a typical blast wave, peak
(Ref 2, 13& 25), Bernal(Ref 1) studied the des-
pressure is the press increase at the shock tructive effects of blast on living organisms and
front or the highest press in the wave minus atmospheric
various objects and found that a press wave of
press, and is a measure of the max force exerted by the
6 kg/cm2 kills a man while O.O7 to 0.7 kg/cm2
blast wave. Impulse is mathematically equal to the
destroys window panes. A comprehensive study
positive phase and is a measure of the force
of pathological effects of blast from expl devices
multiplied by the duration. The negative phase
in air, underground and underwater is reported
lasts considerably longer than the positive
by Valade (Ref 20)
phase but the max negative press is only a
The relative air blast effectiveness of
fraction of the max positive press (See Ref
various expls is indicated in the following
12,p 65ff)
table: (See also Refs 6,13,16,17,19,21,25,
In general, both peak press and impulse must
26&27)
exceed certain min values in order to demolish
various structures. Stmctures that are strong See Chart Next Page
 I

B 182

Peak pressure Effectiveness against

(at equal. load-bearing wall
Explosive distances) construction
Radius Area
Torpex (RDX/TNT/AL: 42/40/18) 122.5 125 156
HBX (RDX/TNT/AL/Wax: 117.5 120 144
40/38 /17/5 ) . . . . . . . . . . . . . .
Minol (NH4N03/TNT/AL: 115 117.5 138
40/40 /20) . . . . . . . . . . . . . . . -..
Tritonal (TNT/AL: 80/20) . . . . . 112.5 117.5 138
DBX (NH4NO#RDX/TNT/AL: 112.5 i12.5 127
21/21 /40/18 ) . . . . . . . . . . . . .
RDX Comp B (RDX/TNT: 60/40) . 110 110 121
Ednatol (Halite/TNT: 57/43) . . . . 105 105 111
TNT . . . . . . . . . . . . . . . . . . . . 100 100 100
Picratol (Expl. D/TNT: 52/48) . . 100 100 100
Amatex (NH4N03/RDX/TNT: 100 97.5 95
43/9/48 ) . . . . . . . . . . . . . . .
Amatol (NH4N03/TNT: 50/50) . . 95 87.5 77

Relative blast effectiveness of various explosives.

TNT= 100
the confining surfaces. For example, a blast
Blast Effects Due to Reflected Shock Waves. wave traveling through a tunnel, corridor,
Blast waves are reflected from solid sur- trench or even a street, decreases in intensity
faces but not in the same manner as sound and much more slowly than the saint wave in the
light waves are reflected. When a bomb is open. If a bomb detonates within a building,
detonated at some distance above the ground, there is considerable reflection of the blast
the shock wave spreads out almost spherically wave, even if the walls are demolished. The
until it strikes the ground. This initial wave, overall effect of confinement of blast waves is
called the incident wave, is reflected by the to increase the vulnerable radii of demolition
ground surface. At a certain distance along and visible damage(Refs 3,13, 19&25)
the ground, from the point immediately below The underground and underwater blast
the bomb, the reflected wave combines with effects of an expln are more comparable with
the original or incident wave to form a third its open-air effects than with those observed
wave which has a vertical front at ground under confinement(Ref 19)
level. This third wave is called a Mucb wave Blast Effects in Earth (Underground Blast).
and the point where the three waves intersect An expl chge which is detonated while buried
is called the triple point. At the triple point, deeply in earth exerts pressure almost entirel~
where the incident wave is reinforced by the on the earth about it and causes movement
reflected wave, both peak pressure and im- effects over a distance known as radius of
pulse are at a max and each is considerably rupture. If the depth of burial is less than the
higher in value than that exerted by the radius of rupture, the expln products blow
original shock wave at the same distance through the surface of the ground and form a
from the point of expln. The Fig on next page roughly circular depression known as a crater.
illustrates the formation of a Mach wave and An expln on the surface of the ground makes
shows the path of the triple point a shallow crater, which may have a greater
Thus by controlling the height of deton, it is diam than that produced when the expl is
practicable, utilizing the phenomenon of Mach buried. This is due to the scouring action
reflection to control the region of max blast of gases projected downard from the expl chge
effect (See Ref 12,p 65fi) Important factors in crater formation are the
Blast effects are enhanced also by con- type of earth cratered and the type of expl
finement, due to reflection of blast waves by used. Expln of a moderate chge in soft,

——
 B183

MACH REFLECTION

—math wav.

FORMATION OF “MACH WAVE’’ ANO “TRIPLE POINT:

swampy ground makes a relatively huge crater, surface known as camouflet (Refs 19& 25)
while in a rock formation only a small crater Mixts of AN with high percentages of Al are
will be formed. An expl of low deton rate, that very effective for air blast, underground and
produces a large vol of gases, may form a underwater use because of their long mainten-
larger crater than TNT, if the chge is well ance of sustained pressure, despite their low
below the surface and the ground is not too brisance. The use of cratering operations in the
hard or rocky. If the chge is on the -surface, a field has led to the development of special
low-rate expl makes a smaller crater than TNT blasting expls (qv), including AN compns. These
because of the weaker scouring action of the are not to be confused with expls of high deton
lower velocity gases rate, such as Comp C-3 & Comp C -4, ,which
The volume, in cu ft, of a crater produced are used to produce earth shocks(qv)(See Refs
on average soil by coml dynamite is given 6,17&26)
by the equation: V=O.4W ~ ,, where W is the wt Blast Effects in Water (Underground Blast).
of dynamite in lbs. This equation is not Extensive studies of underwater explns were
applicable to military bursting chge expls as conducted by A. Stettbacher and some of his
they are more effective cratering agents than results are given in Ref 23. The deton of HE
are coml blasting expls. Since cratering effect underwater results in shock waves of extremely
is considered to measure to some extent the high pressures, which decay rapidly with dis-
demolition effects of GP bombs, these bombs ta nce from the chge(Ref 15). Since the total
are sometimes tested for size of crater produced. damage is due to both the shock wave and the
The formula v=4. 13w, where V is the VO1 of subsequent bubble pulses, these effects must
crater in cu ft and W is the wt of expl in lbs, be separately evaluated(Ref 8). One measure-
has been found to apply for 500 & 1000-lb TNT ment to make is that of the periods o/ oscil-
bombs lation of the bubble, that is, the time intervals
If an expl is buried at a depth exceeding the between successive minima in the bubble radius.
radius of rupture, the compression effect down- The length of the bubble period is related, to
ward and horizontally and the lifting with sub- the energy left after passage of the shock wave,
sequent subsidence cause a depression on the by equations discussed by Swift, Jr & Decius
 B 184

(Ref 8). In general, the longer the bubble period, A,S. Pitcher, PrRoySoc 243A, 534-45( 1958)
the greater is the energy 25) C.G. Dunkle, “Blast Effects in Air, Earth
.4 second ~easure of the energy may be obtcl from and Water”, PA-Stevens Inst Technol Syllabus,
a study of the max & min radii of the bubble. Session 26 (1958), 311-19 26) H.J, Goodman,
By a combination of radius and period measure- “Compiled Free-Air Blast Data on Bare Spherical
ments, calculations of energy and other para- Pentolite”, BRL Rpt 1092 (1960) 27) G.F.
meters have been made(Ref 8). Working with a Kin ney, “Explosive Shocks in Air, ” Macmillan,
Iiq contg gas bubbles, Campbell & Pitcher(Ref NY ( 1962)
24) found evidence that, in a collision between
two shock waves moving in opposite directions, Blast Effects, Measurement of. See under Blast
the strengths of the two shocks are unaltered Meters
by the interaction between them. Cole(Ref 10)
considers in detail the sequence of events in BIast-furnace Dust(Gichtstaub in Ger). It was
an underwater expln. (See Ref 12,pp69-71 and used in some expl compns Re/.’ Kast-Metz ( 1944),
also Depth Bombs & Antisubmarine Bombs 467
under 130hf3S)
Re/s: 1) J. D. Bernal, PrRoyInst (Gt Brit) 31 II, Blastine. A safety expl consisting of a mixt of
235( 194 1) 2) ya B. Zel’dovich, RabotyKhimInst- NH4C104, NaNOa, DNT & 5Z paraffin wax(Ref 1).
AkadNauk 1941-43, 214 3) J. R. Newman, ‘<The It was claimed by Kedesdy to be 50% more power-
Tools of War,” DoubledayDoran( 1943), 360 ful than dynamite. According to Barnett (Ref 3)
4) Anon, APG ‘ordnance Proof Manual” OPM this is a Swedish expl, but Stettbacher (Ref 4)
40- 34(1944) 5) J. G. Kirkwood & S. R. BrinkIey,Jr, and Thorpe (Ref 5) report a British expl called
“Theory of the Propagation of Shock Waves from Blastine which consists of NH4C104 60, NaN03
Explosive Sources in Air and Water;” OSRD Rpt 22, TNT 11 & paraffin 7%. Marshall (Ref 2)
4814 ( 1946) 6) Anon, “Comparison of Blasts of notes that the expl Blastine was used exten-
Different Explosives, ” HEC Translation, sively during WWI. Kostevitch (Ref 3a) gives for
Kummersdorf, April 1944 (147 pictures of explns) a Blastine used during WWI: NH4C10463, NaN03
7) G. Grime& H. Sheard, PrRoySoc 187A, 357-80 23, DNT 8 & parrafin wax 6%.
( 1946) & CA41, 1437( 1947) 8) E. Swift, Jr & Refs: l)E.Kedesdy, SS 3,97(1908) 2)Mar-
J. C. Decius, “Measurement of Buble Pulse shall 1(1917),387 3) Bamett(1919), 112 3a)M.M.
Phenomena” III, UERL Woods Hole Oceanogra- Kostevitch, “Burning Ground”, Imp d’Art Vol-
phic Instn, NAVORD Rpt 9746(1947) 9)E. taire, Paris(1927),40 4)Stettbacher(1933 ),316 5)
Dubois, RevScientifique (Belg - Fr) 84, 323 (1948) Thorpe 4(1940),464
10) Cole, Underwater (1948), 3-13 11) T. Urbansk~
PrzChem 4, 487( 1948) 12) W.A. Noyes, Jr, Edit, Blasting. A process of loosening rocks, earth,
‘Science in World War II, OSRD Chemistry” coal, ores and other materials by the use of
(1948)! 58 ff&84-7 13) W.R. Tomlinson, Jr, expls is called blasting. The blasting action
“Blast Effects of Bomb Explosives” ( 1948) may be that of a shattering, percussive or heav-
(PA Tech Div Lecture, 29pp) 14) G. Taylor, ing nature, depending upon the type of expl used
PrRoySoc 201A, 159-74( 1950) 15) H.G. Snay & and the method of placing it within or near the
J.H. Rosenbaum, “Shockwave Parameters in material to be blasted
Fresh Water for Pressures up to 95 Kilobars, ” Limiting charge is defined as the max per-
NAVORD Rpt 2383(1952) 16) Armament Engrg missible chges of an expl used in gas-endangered
( 1954), 185-97 17) CO1l, “Symposium on Blast mines. Seleznev(Ref 4) tested the validity of
and Shock Waves, ” HA, England (1955) 18) F. this concept by firing charges of various wts
Berry et al, PrRoySoc 227A, 258-70 (1955) & (including chges exceeding considerably the wt
CA49,7249 (1955) 19) TM9-191O (1955), 72-6 20) of a limiting chge) of safety and unsafe expls.
P. Valde, MP 37, 367-412(1955) 20a) O.E. Shef- The limiting chge concept proved to be without
field, PATR2353 (1956)(C) (Blast props of expls foundation in fact, provided the chge was made
contg Al or other metal additives) 21) Cook to do work, that is, spend itself on blasting coal
(1958), 353ff 22) D.W. Boyer et al, “Blast from or rock. If the chge misfired or was faultily
a Pressurized Sphere”, Univ Toronto UTIA Rpt placed, then any wt of it (safety or unsafe expls
48 (1958) 23) PATR 2510(1958), Ger 212-13 is dangerous, In view of these results, Seleznev
(Unterwassersprengstoffe) 24) I.J. Campbell & (Ref 4] suggested a revision of the safety rules

—-..-—-—...——
-1
 B 185

Suzuki (Ref 3)patentedanapp with liq C02 strength desired

expl to be used instead of dynamite in coal The modern blasting cap may be defined as a
mines. Jinda et al (Ref 6a) reported that the device intended to initiate by means of a detonat-
toxic gases COZ,CO & N02 are evolved from ing wave a HE, coml or a military demolition chge.
exploded cartridges in testing’ galleries and in If such a device is used as a part of an expI train
metal ore mines. ,Lechner in Explosivst 1959, in a projectile or a bomb, it is called a ‘Detonator”
33-6 discusses poisoning by gases produced on (qv)
blasting Blasting caps may be of either the non-electric
Numerous handbooks, pamphlets and other refs or electric type:
describing the blasting process are available. I) Non-electric Blasting Caps may be subdivided
See also Ammonium Nitrate Blasting Explosives, into single component and compound(or composite)
Vol l,p A341; Ammonium Nitrate Dynamite, caps
Vol l,p A355; Ammonium Nitrate Gelatin, Vol 1, a) Single-component Cap consists of a smaIl
p A367; and Blasting Explosives in this vol metallic tube cIosed at one end and partially
Refs: l)Colver(1918),485ff & 560 2)Ensign-Bick- filled with an Initiating Composition(see under
ford Co, “Efficient Blasting & Prevention of Blast- Blasting Caps, Charges and Compositions for).
ing Trouble “,P amphIet( 1941 ),22pp 3)Y.Suzuki, A piece of safety fuse(Bickford fuse) with a fresh-
JapP 3,4&5 (1950)& CA 46,8376(1952) 4)A.I. ly-cut end, pricked with a pin, is inserted into the
Seleznev,Ugol’ 26, NO 5, 29-30(1951)& CA 45, open end of the cap and pressed firmly against
8248(1951) 5)B1asters’ Handbook(1952) 6)F. the charge. With the aid of a special device, the
Weichelt, ‘Handbuch der gewerblichen Spreng- open end of the cap is crimped tightly (as near
technik”,Marhold, Halle/Saale(1953 ) 6a)T.J inda the top as possible) around the fuse, taking
et al, JIndExplsSoc(J apan)14,210-12( 1953) & CA care not to squeeze the cap near the explosive
49,11281(1955) 7)B.Stoces, ”Introduction to chge because of the danger of inducing an ex-
Mining’’, Lange, hiaxwell & Springer, London NW, plosion. The cap is then inserted in a cartridge or
VOIS 1 & 2(1954) 8)H.Stapf,’’Bergbauchemien, block of HE and the fuse is ignited by the flame
Fachbuchverlag, Leipzig( 1954),427pp 9)Imperial of a match or squib. The flame of the fuse ignites
ChemIndustries Limited, “Blasting Practice”, the initiating mixt causing it to explode. The deton
Pamphlet, 2nd Ed, The Kynoch Press, Birmingham wave thus created causes the expln of the main
(1956) 10)0. Kiihnl, “Hancluch der Sprengtechnik’, chge(dynamite cartridge etc)
Verlag des Osterreichischen Gewerkschaftsbundes, These blasting caps are usually made in eight
Wien(1958), 155pp 1 l)hiinistry of Power, “The strengths, No 1 the weakest and No 8 the strongest
Use of Explosives at Quarries”, HhiSO,London The present practice in the US is to manuf only
(1961 ),60pp No 6 and No 8 caps. The single-component No 6
contains a mixt of 0.8g h4F with O. 2g KC103; the
BLASTING CAP (also called Commercial Detonator) No 8 cap contains 1.6g hfF + 0.4g KCIOa or their
(Ziindkapsel Ziinder or Sprengkapsel in Ger; I)eto- equivalents
nateur in Fr; Detonator in Rus; Detonadore d a mina b) Compound Cap. Some HE’s such as TNT, PA,
in Ital and Cebo or C apsula detonante in Spa@, RDX compositions, Pentolite etc, cannot be initiat-
When bIack powder was used exclusively for ed with certainty by either a No 6 or No 8 cap and
blasting, charges were exploded by igniting them it is necessary to combine them with a booster or
with miner’s fuse, or by other igniters. Then NG to use a cap with two components(layers), one of
and dynamite were invented, it was found that which is an initiating (primary) charge(such as hfF)
they could not be exploded by such means of and the other is a base(main or secondary) charge
ignition, hence a different device was neede~ -one (such as pressed PETN). In these caps the base
which produces a deton wave. The problem was charge acts as a small booster
solved by Nobel in 1867( BritPat 1345) with his A typical example of such caps is one which
in-rention of the blasting cap. The first cap c.::- consists of a small metallic capsuIe(C~ Al or
sisted of a copper cylinder closed at one end and gilding me d) 11‘S to 17’s” long and I ja” in diam, press
partially filled with hlF, which was exploded by -loaded at the base with tetryl, PA, P?TIN, ??W, HNIJnt
the flame of a miner’s fuse. The explosion of MF or loose TNT to form a main chge(ca 0.4.g for N06
produced a deton wave of great intensity, which cap and 0.55 -O.9g for No 8 cap). Above this is
caused the expln of the dynamite chge. The placed a layer of priming expl, such as hiF w/wo
charge of MF was varied to provide the initiating KCIOa & Sb2S3(ca 0.4g for No 6 cap and ca 0.5g
 1

for No 8 cap),or LA/LSt(ca 0.2g for No 6 cap called “two-part detonators” because they contain
or 0.25 -O.3g for No 8 cap). One of the modern two layers: priming and base
No 8 caps contains 0.55g PETN & 0.25g LA. A stronger cap, now called US Army SpeciaI
There are also larger caps, such as US Army BIasting Cap, designed by the US Corps of
Special Cap described below and No 16 cap Engineers aIso belongs to the compound type.
mentioned in USP 2860041(1958). The latter cap It is described here and also in Ref 30
consists of a large cap contg a base chge of Western Big Inch Blasting Caps, manufd by Olin
PETN into which is slipped a regtdar No 6 cap Industries Inc, East Alton, Ill, are made of Al
thus forming a single unit equivalent to 1. 5g and contain RDX as a base chge. They are 1 1/8”
PETN(base chge) & 0.25g LA(prirning chge)(Ref31 ) long and 15/64” in diam and are about as powerful
MF is used now only in some foreign countries, as the 1 5/8” long conventional cap. Because of
but very seldom in the US(Ref 37) their smaller size, there are some advantages in
In order to improve the performance of the cap, storing and handling them
the initiating chge is sometimes covered with a It is also possible to prep three-component caps,
rein~orcing cap. This is a small perforated cap similar to detonators of the same type(see under
made to fit snugly against the inner wall of the Detonators)
main cap. Reinforcing caps ate used only with It is of interest to note that compound caps and
MF chges and are not required with LA chges. With detonators were developed in the US, by the DuPont
these caps the safety fuse is inserted and crimped Co, as early as 1912, but it was not until 1916
as described for a single charge cap. In these caps that a real advance was made when tetryl was first
the deton wave used for the base charge
created by an in- Principal uses of non-electric blasting caps are
Compound Cap itiating expl is in quarry and agriculture work and in ore mining
~ Metallic Cap reinforced and H) Electric Blasting Caps (also called Exploders,

14
speeded up by Electric Initiators or Detonators, or Fusees)
Reinforcing Cap
the deton of the Since non-electric caps are fired by a safety
base chge expl, fuse, the time of firing is governed by the length
Priming Charge
such as tetryl, of fuse and its burning rate; consequently it is
II which possess- not practicable to use these caps for firing

I.t
es a much high- several shots simultaneously, as is required in
Base Charge
er deton vel than most blasting operations. For this kind of work,
hiF, LA or any elec blasting caps are of great advantage
other initiating Electric Blasting caps may be divided into
expl. This reim “high tension” and “low tension” types
forced detonating Historical. The original elec cap was invented in
impulse wil I ex- 1745 by Dr Watson of England and were improved
plode most expIs of low sensitivity(See Fig) by Benjamin Franklin in 1749. In Franklin’s cap,
At the present time, the DuPont Co manufactures the gap between the two wires was encased in a
two standard No 6 blasting caps, one with an Al charge of compressed BkPdt which acted as ig-
shell 1 3/8” long and the other with a Cu shell niter for the main chge of BkPdr. This device
1 1/2” long. Each has about 3/4” open space above could not detonate the chge but only ignited it
the chge for inserting the fuse and therefore could not be used for dynamite or
Two No 8 caps are also manufd, one with Al,, other HE. Franklin did not exploit his invention
shell 1 5/8” long and one with Cu shell 1 7/8 long, and it was forgotten until 1830, when Moses Shaw
but they are not used extensively in coml blasting was granted a USP at for a similar device in which
because No 6 caps are strong enough to detonate charges of gunpowder were fired simultaneously
most expl. They are used, however, for military by eIec current through the use of a priming compn
purposes containing fulminating silver and gunpowder. The
In order to intensify the deton effect of a blast- device was not satisfactory and Shaw, with the
ing cap, the closed end of the capsule(=business assistance of Dr R. Hare, constructed another de-
endn) is indented towards the inside thus utilizing vice which was the first “low tension” cap. It
the Munroe(Shaped Charge) Effect. Some investigat- contained a fine wire, which was heated to in-
ors question the value of this improvement candescence by means of eIec current from a
The compound caps described above are also battery. As batteries were not convenient for
 B 187

field use, Baron von Ebner of Austria, in the the cap from accidentally being fired by static
1850’s, invented che first elec friction machine electricity developed in the human body, from
suitable for field use. The machine was improved friction or from stray radio frequency waves, one
in 1869 by H. J. Smith of Boston and was used in of the leading wires touches the wall of the
the blasting of the Hoosac tunnel. Mowbray modif- cap at some distance from the ignition compn
ied it and called it a ‘Powder Kegwq but it was b) Concave Plug Type (Type 2) contains a base
not as good as the original device of Smith. The chge (usually Tetryl, RDX or PETN) in the
first magneto-electric apparatus was invented in bottom of the cap, covered with a smaller chge
1856 by Sir C. Wheatstone while working for of initiating expl(such as MF or LA). The bridge
Sir F.Abel wire is imbedded in an ellipsiod consisting of a
A) High Tension Cap contains a sensitive priming cemented ignition compn which is generally in a
mixt packed around a break(gap) between two plastic condition when applied and hardens on
pieces of wire; the outside ends of the wires are drying(See Type 1 Cap). In order to facilitate the
connected to two poles of a magnet or other app application of this compn to the bridge wke, the
producing a high tension current. T/hen the smaller base of the conical plug holding the
circuit is closed, a spark jumps across the gap bridge wires is made concave
between the wires and ignites the primary mixt. c) Match.bead Type (Type 3) contains in the bottom
These caps have been practically superseded by: of the cap, a base chge(such as Tetryl, RDX or
B) Low Tension Caps. Electric blasting caps PETN) covered with an initiating chge(MF or LA).
presently used in the USA consist of a cylindrical The ignition device consists usually of a flat
metal shell containing a detonating base chge, an strip of insulating materiaI, the two faces of which
ignition compn and an elec firing device having ate covered with metallic foil each soldered to a
a high-resistance wire(bridge) between the two leading wire. A bridge wire passes around the end
leg wires of the firing circuit. When the current of the strip and connects to the ends of the Ieading
is applied to the elec circuit(either by blasting wires. After this, the bridge wire is dipped into
machine or from a circuit connected to a power a plastic ignition compn which dries to form a
line), the bridge is heated to incandescence hard, tear-drop shaped pellet similar in appearance
thus firing the ignition compn. This in turn acts to an ordinary matchhead. For this may be used Cu
on the initiating compn(such as MF, LA, etc) acetyIide or Ag azide or LSt(yel variety) in NS
and this detonates the base chge, such as Tetryl, gelatinized with amyl acetate; mixt of Cu acetylide
RDX or PETN. Sometimes, as in the “bridge plug K chlorate& carbon in collodion. The remaining
type” caps, base and initiator chges are combined parts are the same as in Types 1 and 2
in one chge(see below). Because of the danger of (See also Ref 8)
detonation from stray ground currents, strong radio See Figure next page
frequency impulses, ar accidental closing of the Copper brass and aluminum may be used as
elec circuit, elec cap leads and circuits are material for the cap(shell) itself
always short-circuited until immediately before Many other ignition compns have been patented
firing such as: bis-triethyl lead styphnate, triethyl lead
Burrows et al of DuPont Co(Refs 9 & 10) de- -basic lead styphnate, triethyl lead azide, mono
scribe the following types of elec caps; -triethyl lead azo-aminotetrazole, bis-triethyl
a) Bridge Plug Type (Type 1 ) contains base chge lead azoaminotetrazole, triethyl lead azidodithio-
(such as Tetryl, RDX, or PETN) combined with carbonate, diethyl lead diazide & his-basic diethyl
priming expl(such as LA). On top is placed PI astic lead styphnate, etc. The ignition compns mention-
ignition chge(such as Ag or Hg salt of chlorinated ed above have an “overall lag” of Ie ss than
azidocarbonamidine in NS gelatinized with amyi 0.0009 sees when fired at 12 amps. but in’ some
acetate; Pb picrate or LSt or Ag azide in NS cases this lag is even smaller, viz, 0.0002, 0.0003,
jelly; mixt of Cu acetyIide, K chlorate & carbon 0.0004, 0.0005 or 0.0006secs
in collodion). A high resistance bridge wire, In addn to the initiating compds mentioned
connected to two leading (leg) wires of the firing above(MF and LA) the following may also be used:
circuit, is imbedded in the mixt. These wires LSt, DADNPh, TATN13, Cyanuric Triazide,
are held in a fixed space relationship by means Tecracene or a mixt of LA 80-90 & K chlorate 20
of a plug, usually shaped like a truncated cone. - 10%(See also Additional References on Blasting
A waterproofing compn, covered with cast sulfur, Cap Compositions, which are given below)
is placed on top of the cone. In order to prevent A special blasting cap, particularly suitable in
 I

B 188

8-
8

Type 2 Type 3
Type 1

ELECTRIC BLASTING INITIATORS

1- Metal capsule or shell 11- Elbow in leg wire

2- Base charge 12- Insulation
3- Priming charge 13 – Concave plug
4- Ignition composition 14- Elec connection between shell wall
5 – Bridge plug & leg wire
6- Leg wire 15 – Insulating material
7- Leg wire 16- Tab
8- Bridge wire 17 – Shoulder
9- Waterproofing compn 18- Paper cylinder
10 – Sulfur seal 19- Elec conducting plug

seismographic explorations for mineral fir other Delay caps are manfd in the US by DuPont Co,
deposits, was invented by Burrows & Hand forth Olin Mathieson and other concerns
(Ref 4). This cap contains a bridge wire which US Army Special Blasting Caps, formerly known
cannot be melted by the passage of a discharge as Special Army Engineers’ Blasting Caps. Many
from the ordinary elec blasting machine(manually of the demolition expls used by the military forces
operated elec dunamo) with max voltage of 225 in the field are HE’s such as compressed TNT,
volts and an instantaneous peak amperage of compressed NS expl and Composition C-3 and
15amps. The wire is 0.005” diam(in lieu of 0.0025° C-4 cannot be detonated with certainty by coml
Ni/Cr wire which usually melts by current of blast- blasting caps. Special larger caps, both elec
ing machine) and is constructed of an alloy: Ni 80, and non-elec are made for this purpose:
Cr 20. The passage of the current through this The nonelectric cap, called Type 1 con-
wire heats it to such an extent as to fire any of sists of an $ alloy “52S” shell ca 2.35” long
the ignition mixts in use at present and ca 0.235 in diam, closed at one end. The
Delay electric blasting caps are similar to regular charge consists of 13.5 grains of PETN or RDX
elec caps except that a delay element is inserted (base chge) and a sufficient amt of LA(priming
between the electrical firing element and the det- chge) to insure complete detonation of PETN or
onating (base) chge. They are used to detonate RDX. Both chges are compressed into the shell
charges of dynamite in rotation, giving more ac- so that not less than 0.75” above the chge is
curate timing of the delayed shots than is possible left empty for insertion of a suitable safety fuse
with non-electric caps and fuses. The delay time The electric cap, called Type ![ consists of an
of each intervening cap is such as to prevent Al alloy “52S” shell ca 3.15” long and ca 0.275”
overlapping between delay periods. These periods in diam, closed at one end. The charge consists
are usually equal to 0.8-0.9 secs(See also Ref of 13.5 grains of PETN or RDX compressed into
22,pp 97-9) the shell. A priming chge(LA) and igniter are then
 B 189

inserted. The igniter bridge wire is connected to P61voras(1952),134-7 24a)Belgrano(1952 ),247-52,

terminals of two copper leading wires, each 12-ft 25 )PATR 2 ]45( 195 5),pp RUS 4-5( Conf) 25a)Cook
long. The cap is sealed to make a waterproof (1958),16-17 26)Taylor & Gay(1958),52-67(17
assembly(Ref 30,pp 2 & 3) refs) 27)PATR 251~1958),34-5 28)US Specific~
(Compare with Detonators and with Blasting Squibs) tions on Blasting Caps: AlIL-C- 10592 (Electric);
British Blasting Caps (Commercial Detonators). The MIL-C- 11762(EIectric and non-electric); MIL-C
nonelectric caps are described in Refs 12,20,23 & -20448( l)(Electric) 29)US Specs on Detonators:
26. Although the majority of caps used in Brit in- MIL-D-20503(Ele ctric Ail ); MIL-l?-20462A(E lectric
dustry are either No 6 or No 8, sizes ranging from M36Al); JAN-D-409( Delay Ml & M2) 30)USSpec
No 1 to NO 10 are available for experimental or MIL-C-140003A(Caps, Blasting, Special) 3 l)~~m.
other purposes. Until recently the detonator chge H. Rinkenbach, Allentown, Pa; private communication
consisted of a mixt of MF & K chIorate, but this (1962) 32)G. D. Clift,Chemical Center,Md; private
has been replaced very largely by ASA-Tetryl or communication(1962)
ASA-PETN detonators(See ASA in Vol l,p A493
of this Encyclopedia and Ref 26,p 55). Generally
speaking, ASA detonators are stronger than ful- Additional References on Blasting Cap Compositions
minate detonators of corresponding numbers, but In addn to the commonly-used chges mentioned
Brislra Detonators are even stronger under Blasting Caps(above), the following listing
British Electric Detonators are described in Ref shows the variety of chges and modifications pro-
26,pp 56-65 posed by various investigators:
British Delay Detonators are described in Ref 26, l)Vestfa lisch-Anhaltische Sprengstoff A-G, GerP
pp 69-85 176719( 1~04) & CA l,1503(1907)(Priming compns
French Detonators. See Refs 4 and 6 contg Pb and Hg chromates as substitutes in whole
German Detonators are described in Refs 7 & 27 or in part for KC103, with further addn of alk earth
(See also Refs 1,2,5 & 19) or heavy metal oxides, if desired) 2)K. W. Will,USP
Italian Detonators are described in Ref 24a 827768(1906) & CA 1,122(1907)(A priming compn:
Russian Detonators. See conf Ref 25(8 unclassified Tetryl 50 & MF 50%) 3)~’.C.White,BritF’ 19983
Refs) (1906) & CA 1,2518(1907) (A priming compn: MF
Spanish Detonators are described i n Ref 17 (See 87.5 & AgF 12.5%) 4)L.Wohler, GerP 196824(1907)
also Refs 17a & 24) BripP 4468(1908) & FrP 387640(1908); CA 2,2302
Re/s: l)C.Herlin,SS ]5,137-40(1920) 2)Nao6rn, (1908) & CA 3,592,1690( 1909)(Small quants of the
Expls( 1927),187 3)Van Gelder & Schlatter( 1927) heavy metal salts of hydrazoic acid are used as a
4)Vennin,Burlot & L6corch6 (1932),568-70 substitute for MF as a primary chge for detonators
5)Stettbacher(1933 ),345-55 and Figs 209,214,215, and as an exploder, either alone or together with
216 & 217 6)Pepin Lehaleur(1935),366-71 small amts of expl agent) 5)A. Lang,GerP 209812
7) Beyling & Drekopf( 1936),150-239 8)W.H.Aughey (1908) & CA 3,2228( 1909)(A MF priming compn
et sI,USP 2086527(1937) & CA 31,6466(1937) which does not produce rust, is obt by omitting an
9)L.A.Butrows et al, USP’S 2086530, -1, -2 & -3 O carrier md adding Mg or Al powder meIted with
(1937) & CA 31,6466-7(1937) 10)L.A.!3uITows et S in equiv amt. The proportion of MF to metaI-S
al, USP 2105635(1938) & CA 32,2357(1938) mixt varies from 1:1 to 2:1) 6) L. Wohler, USP
ll)L.A.Burrows & S. L. Handforth, USP 2153171 904289( 1909) & CA 3,717( 1909)( Superimposed
( 1939)(not found in CA) 12)W.TayIor,Chem & layers of PA & LA are proposed for filling caps)
Ind 58,1065-9(1939) 13)Davis(1943),413-24 & 7)Stahl & NoIke, GerP 239162( 1910) & CA 6,2170
Fig 95 14)Meyer( 1943) 332-4 15)R. L. Grant, (1912)(A non-poisonous priming compn is prepd by
“Structural Feature’s of Typical American mixing P4S$ with S and fusing or tre sting with a
Commercial Detonators”, US BurMines RI No solvent) 8)H. Maxim,USP 988799(1911) & CA 5,
3696(1943) 16)R.w’.Lawrence, USP 2350172(1944) 2179(191 1) [An expl compn for initiating HE’s
17)Vivas,Feigenspan & Ladreda 4(1945),297-321 consists of Ca or Si 8.5 to 18, Pb304 68 to 81 and
17a)P6rez Ara( 1945),655-63 18)P. E .Narvarte ,USP a gelatinized mixt of NG/NC(70/30) 10 to 15%]
2377804( 1945) 19)Stettbacher( 1948), 105-7 9)Eley Bros,BritP 2682(1911)& CA 6,294(1912)
20)A.R.Ubbelohde,TrRoySoc 241 A,215 & 217(1948) (An initiating compn for use in detonators and the
21)Olin Industries Inc, ‘ ‘Explosive Products” ,BuII like, composed of MF ~ Ba02 & TNT or known
(1950),25-38,736 & 741 22)Blasters’ Hdb(1952), substitutes therefore; such addns being substituted
92-9 23)Taylor(1952), 10-11 24)Stettbacher, in whole or in part for KC103, commonly employed)
 1

B 190

10)W.Meyer,BritP 21337( 1911) &BritP 23493(1911) 21)C.Claessen,GerP 288655(1913) & GerP 289446
&CA 7,1100& 1291( 1913)[Manuf of initiating (1914); CA 10?2800 & 3162( 1916)(Use of 1,2,3,4,6-
compns by employing B a(N03 )2 with or without or 1,2,3, 5,6-Tetranitroani sole in primers is pro-
Pb02, instead of the usual KC103. Eg: MF 25, posed) 22)H.C.Pritham,USP 1048207(1913) &
Ba(N03)2 25, Pb02 35 & Sb2S3 15%. An addn to CA 7,703(1913)(A priming mixt contg KC103, MF
the principle patent adds K picrare to increase & Sb2S3 bonded with Portland cement 2 to 4%)
expl power 1 ll)E.Goodwin,USP 1029287(1912) 23)hLP.Swope,USP 107394(1913) & CA 7,3842
& CanP 147426(1913); CA 6,2533(1912) & CA 7, (1913)(A priming mixt consists of guncotton 20,
2118(1913) (An initiating compn made of MF, a amor P 5, KC103 37.5 & Sb2S3 37.5%) 24)C. Clae&
peroxide and TNT; said peroxide and TNT being sen,FrP 459979(1913), BritP 13086( 1913) & SwedP
substituted in whole or in part for KC103 common- 40379(1916); CA 8,3238, 3860(1914) & CA 10,1597
ly employed) (Compare with Ref 9) (1916)(A cap for use in mines and for military
12)R.Calvet,GerP 26323 (1912 ), BritP 9597(1913), purposes, containe a chge of a nitrated compd, a
BritP 13501 (19~3) & SwissP 62590(1913); CA 7, chge of LA & a chge of NF or hlF mixed with
4072(1913) & CA 8,2254,3366,3860( 1914)(A priming KC103) 25)C.Claessen, FrP 463714(1913) & Brit
compn employing Cu perthiocyanate in admixt with P 24839(1913); CA 8,3238(1914)& 9,1249(1915)
KC103 or KC104) 13)Y~.H.BueH,USP 1027814 (A secondary detonator for large quants of other
(1912) & CA 6,1991(1912) (A priming mixt consistg expls, prepd by using Hexanitroethane, alone or
of Sb2S3, Pb(SCN)2, KC109 & TNT) 14)A. J aques mixed with other compds, such as TNT. The
& G. Wells, BritP 23450(1912) & USp 1106147(1914); mixt of Hexanitroethane 45 & TNT 55% detonates
CA 8,1347 & 3238(1914)(A priming compn contg di- with a very small quant of MF and can cause deton
benzoyl peroxide 40 & MF 60%. Another example of other expls) 26)C.Hartmann,BritP 18354(1913)
is dibenzoyl peroxide, Pb or cuprammonium thio- & CA 9,381 (1915 )( HNDPhSfi in tryst uncompressed
sulfate & KC103 ) 15)’W.Meyer,BritP 25550(19 12) or compressed condition is proposed as a base
& CA 8,1509(1914) [Modification of e arlier patent ch~ in primers & detonators )( Compare with Ref 20)
(Ref 10) by adding silicides to alk earths. Examples 27)Rheinisch-Testf alisch Sprengstoff A-G, GerP
of priming compns: hfF 20, Ba(N03 )2 40, Pb02 10, 277566(1913) & CA 9,862( 1915) [A priming compn,
Sb2S3 20 & Ca2Si 10% or MF, Ba(N09 )2, K picrate, manufd from N sulfide in admixt with an oxidizing
Sb2S3, Ba2Si & glass powd] 17)E.von Herz,Brit P agent, such aS Pb02, B a(N03)2, Pb(NO~ )2 or KMn-
27198(1912) & CA 8,1672( 1914) (One example of an 04] 28)C.Claessen,GerP 28440q1913) & CA 10,
initiating compn, employing Diazoperchlorate, 970( 1916)( Chges for mining & military initiators
consists of lg PA and 0.02g Nitrodiazobenzene may consist of 0.85g Tetryl, 0.15g LA and 0.05g
Perchlorate; the two chges being separated by a K picrate or of 0.85g Tetryl, 0.15g LA and O.10g
sheet of Cu foil or Sn; and the whole enclosed in KC103 with 20% sugar) 29)A.Voight,USP
Sn foil or perforated sheet Cu and varnished) 1095302(1914) & CA 8,2253(1914) [A priming
18)Sprengstoff A-G CKUbonit ,GerP 269826( 1912) & compn constg of Na nitrocresolsulfonate 25,
CA 8,2253 (1914)(An expl, for primer & detonator NaN03 or KN03 65 & KC104(or KC103)10%. Na
caps or for filling projectiles, torpedoes or nitrophenolate may also be used and an equal amt
mines, is prepd from Hexanitrodiphenyl sulfide of TNT may be substituted for KC104 or KC103 in
in HN03 by treating it with oxidg agents, to yield the above mixt] 30)~~.H.Buell ,Britp 21082( 1914),
Hexanitrosulfobenzide) 19)C. F.von Girsewald, USP 1174669(1916) & USP 1184316(1916); CA 10,
GerP 274522(1912) & CA 8,3122 (1914 )( For the 970,1435 & 1791( 1916) (A primer contg an azide
manuf of priming caps an ordinary No 8 Cu capsule with other substances. Eg; NC 3 & LA 1P; NC 11,
is filIed with ca lg TNT & 0.05 -O.lg Hexamethylen e- LA 6 & Na azide 3ps and Na azide 35, Sb2S3 35
triperoxidediamine and the mixt pressed. The Hexa- & KC103 30%) 31)E.von Herz,GerP 285902(1914)
methylenetriperoxidedi amine is claimed to exceed & CA ]0,970(1916) (A priming compn for small
by 4 to 5 times the expl power of hfF ) 20)Sprengstoff arms and other cartridges employs LSt alone or
A-G Carbonit,GerP 286543(1912) & GerP 289374 in combination with O carriers. For example, in
(1913) & CA 10,1272,2800( 1916)( Afillerforprimers, a -No 8 cap, lg TNT, 0.2g LSt & 0.15g MF are sep-
primer caps and the like composed of compressed arately compressed to form a detonator giving the
Hexanitrodiphenyl Sulfide(HNDPhSfi) 0.85g & MF same initiating action as lg TNT & O .555g MF)
0.4g. It is claimed that HNDPhSfi is more powerfu I 32)L.Wohler,USP 1128394(1915) & CA 9,1118(1915)
than either HNDPhA or PA and as the base chge is (A deronator for expl contg LA mixed with ca 3
safer in caps than Tetryl)(Compare with Ref 26) times its wt of MF, with or w/o KC103. This mixt
 B 191

cannot be ‘dead pressed” even at 2000atm press) (Salts of TNR in priming compns. Eg: K or Ba TN-
33)W. L. Main,USP 1147958(1915) &CA 9,2592 Resorcinate 15, Sn sulfide 35 & KC103 50%)
( 1915) (An initiating mixt composed of MF mixed 44)C.M.Stine, USP 1309552(1919)& CanP 206311
with 5-70Y0 KBr03 or other bromate. The brom ate (1920); CA 13,2283(1919)& 15,600(1921) {A
mixt gives a higher initiating force than a similar blasting cap contg dinitroxylene dinitrate [C6HZ -
mixt contg chlorate) 34)W.Runge,USP 1168746 (CH2N03 )2(N02)2] and MF. These two compds
(1916), USP 1185830(1916) &CanP 181129(1917); may be mixed together in 80/20 proportions resp.
CA 10,822,2045(1916) &, 12,6 Nw8)(A primer Such a cap, when ignited by safety fuse or elec-
compn is prepd by mixing LA with 5-30% by wt trically, is an efficient detonator for dynamite or
of TNT, with or w/o a very small amt of gum arabic other HE] 45)W,H. Buell,USP 1311872(1919) &
as binder. This mixt gives more effective initiation CA 13,2599(1919) {A priming mixt made of Trinitre
than a mixt of LA & a chlorate) 35)R.Calvet,USP phenylnitramine, [C6H2(N02)aNH.N02] 15, KC103
1189238(1916) & CA 10,2150( 1916) [An initiating 55 & Sb2S3 30% or TNPhNA 10, Pb(SCN)2-KCIOa 50
chge consists of Cu-perthiocyanate, CU(S3C2N2 ) & Sb2Sa 15ps] 46)C.M.Stine,USP 1313650(1919)
with ca 2.5-3 times its wt of KC103 or KC104. & CanP 198328(1920); CA 13,2763(1919) & 14,
Stable, non-hygr detong chges of similar character 1609( 1920) (A chge of nitrated hemicellulose to-
may be made with CU(S2C2N2), CU(S3 C3N3)Z, gether with TNT, PA & LA and a MF-KC103 mixt
Pb(S2C2N2), Pb(S3C2N2) or Pb(SgC3N3 )21 or other primary chge is suitable for detong dynamite)
36)M.R.Swope,USP 1194095(1916) & CA 1~,2525 47)A.S.Cushman,USP 1325928(1920) & CA 14,633
(1916) [An expl for charging. primers or detonators (1920) [A priming mixt is made of Sb$33 20, KC103
consists of a mixt of NC 18, KNOa 4, Ba(N03)2 50, Pb(SCN)2 25, Tetryl 3-4 & PbO 1-2%]
2.5, Na2C03 0.5, KC103 50 & Pb(SCN)2 25%] 48)W.G.Hudson,USP 1329525(1920) & CA 14,1045
37)C.Clae;sen,SwedP 40749(1916) & CA 10,2525 (1920) (An expl suitable for use as initiating chge
(1916) (A priming compn for caps consistg of a is made of “colloided NC” 1O-2O & LA 90-80%. The
base chge of PETN with an initial chge of MF or “colloided NC” may be NG 93-70 & NC 7-30%)
of LA mixed with KC103) 38)A.J .hfarin,USP 49)E. von Herz,BritP 142823( 1920)& CA 14,2859
1206456(1917) & NorwF’ 29535(1919); CA 11, (1920) (LSt alone, as an intermediate layer between
211(1917) “& CA 14,1441 (1920)(A detong compd of TNT and MF, or in conjunction with other ingred-
the same action as fulminates, azides, etc con- ients, is suitable for use in caps) 50)H.T. Peck,
sists of glycero-Pb chlorates or perchlorates, USP 1350465(1920) & CA 14,3323(1920) (Diplumbic
which can be produced by allowing glycerol or Dinitroresorcinate is used in priming mixts with
other multivalent alcs(such as mannitol, sugar, ground glass, Sb.$3 & KC103 ) 5 l~prengluft-Ges,
glucose, dextrin, etc) to act alone or with PbO on BritP 152335(1920) & CA 15,756(1921) (A detonator
neutral or basic Pb chlorates or perchlorates) chge consistg of paraffin, cork flour & LA and con-
39)0. Matter,USP 1239613(1917), CanP 176609 tained in a perforated rigid material casing, is
(1917) & CanP 176610(1917); CA 11, 3438-9(1917) impregnated with Iiquified gases; such a chge is
& 12, 226(1918) [Caps chged with TNT, Tetryl, used for detonating blasting cartridges similarly
PETN or other nitro compds as a base chge and impregnated] 52)W. Eschbach,BritP 156429( 1920)
LA or a MF-KC103 rnixt as a primary chge. See & CA 15,1815(1921) [Priming compns are made by
also USP 1254147(1918) & CA 12,766(1918)] mixing LA, LSt or other expl compda in the
40)Canadian Explosives Ltd,CanP 183497(1918) presence of a phlegmatizing Iiq of low bp(such
& CA 12,1348( 1918)(HNDPhSfi in tryst or compre - as benzene) in which a small quant of resin has
sed form is a compd suitable for use in caps, been dissolved] 53) R.hf.Cook & B .Grotta,USP
primers or detonators)(Compare with Ref 18) 1385245(1921) & CA 15,3751(1921) (A mixt of LA
41)C.J.S.Lundsgaard, DmP 23470(1918) & CA 13, 40-95 & Tetryl 60-5% is used as a chge for blast-
1152( 1919) [A priming compn composed of a mixt ing caps) 54)Peters Cartridge Co, BritP 165069
of Ca(C103)a, Sb2S3, powd glass with the addn (1921 ) & CA 16,648(1922)( A priming compn com-
of red P and a binder such as shellac, resin or posed of Diplumbic-dinitroresorcinate mixed with
rubber solrt] ground glass, Sb2S3 & KCIO~ ) (Compare with Ref
42)J.Hsr16, USP 1306895(1919)&CA 13,2283(1919) 50) 55)C.J.S.Lundsgaard & K. T. Herbst,BritP
(PETN alone or mixed with nitrated benzene, 168333(1921) & USP 1423233(1922); CA 16,344
toluene, phenols or amines is used as a base chge & 3399(1922) (Perchlorate~ of methylamines may
for detonators) 43)W.H.BueH,USP 1308393(1919) be used alone or mixed with other expls for
& USP 1312156(1919); CA 13,2283 & 2599(1919) shells, mining expls or for intermediate chges
 1

B 192

of detonators) 56)H.Rathsburg, BritP 177744 67)T.Hawkins,USP 1398098(1922) & CA !6,833

(1921)&CA ]6,3399(1922) (Crystcompds of mixed (1922) (PA 16, Pb oxide 48, & KN03 2ps are
trysts & double salts contg the K saIt of Dinitro- mixed together with H ~0 and dried to form an
dinitrosobenzene and difficultly sol salts of expl suitable for use in detonators) 68)W.
hydrazoic acid, Tetrazole derivs, etc are suitable Friederich,USP 1424462(1922) & CA 16,3399
for use in initiators) 57)H.Rathsburg,BritP 185,555 (1922) (Detonating caps for mining or military
(1921) & CA 17,1147(1923) (Expl salts of Tetrazole purposes are formed with a main chge of LA
and Triazole or their derivs are used in detonators, superimposed with a chge of L St) 69) A. Kowastch,
percussion caps, etc. These salts may be mixed or CanP 222375(1922) & CA 16,4067(1922) [A detona-
pptd simultaneously to form double or mixed trysts tor for cartridges contains a carbonaceous sub-
with substances such as NH3, nitrophenols, etc or stance(such as peat) satd with liq air, and mixed
nny also be granulated with paraffin or resins with LA] 70)H. Rathsburg,BritP 201 009( 1922) &
dissolved in C6H6, CC14, etc) 58)E. von Herz, Brit- CA 18,472(1924) (Tetrazenes are used alone
P 187012(1921) & USP 1498001(1924); CA 17,1147 or in conjunction with other ingredients for
(1923) & 18,2605 (1925 )(hfixts of LA & LSt for use primer compns. Eg: MF 30, KC103 25, Sb203 30
as expl priming compns are prepd by simultaneous- & Guanyldiazoguany ltetrazene 15%) 71)E. von
ly pptg the two salts) 59)H.Rathsburg, BritP Herz,BritP 207563(1922)& CA 18,1573(1924)
190215(1921) & USP 1470104(1923); CA 17,3101 (Caps are loaded with one or more of the o- or
& 3920(1923) (A priming compn for loading blast- p-nitrated quinone diazides of polymeric phenols
ing caps consists of the Pb salt of Trinitrophloro- or their metallic salts. These compds are used
glucinol pptd simultaneously with other readily sol either as a top chge over a base chge such as
salts. For example, a mixt of the Na deriv of Tetryl, TNT or PETN, or in admixt with the
TNPhlGl, NaN3 & the Na salt of Dinitrosobenzene usual compn components) 72)J .E.Burns,USP
may be pptd together. The blasting cap may also 143 7224( 1923 ) & CA 17,635(1923) (A priming mixt
contain another substance as top chge) is made of KC103, 30, Pb(N03)2 12, Pb(SCN)z 33
60)W.Friederich, BritP 192830(1921) & CA 17,3255 & powd glass 25%) 73)B.Grotta,USP 1439099
(1923) (Basic Pb Picrate and other basic Pb salts (1923) & USP 1456341(1923); CA17,883 & 2506
of highly nitrated org compds may be pptd simul- (1923) (An initiating mixt which does not readily
taneously to form compns suitable for ase in primers become dead-pressed and is not readily affected
caps or detonators) 61)E.Ott,USP 1390378(1922) by moisture consists of HgN3 20, MF 60 & KC103
& CA 16,344(1922) [Cyanuric Triazide, produced 20%. As a base chge an equal wt of tetryl or other
by interaction of cyanuric chloride & Na azide in HE can be used) 74)W.0.Snelling, USP 1462074
aq soln, is suitable as a priming compn for expls. (1923) & CA ]7,3101(1923) (Detonators are formed
It can be poured while molten(mp 94°) directly with an initial priming chge of MF and a main chge
into detonator caps; it does not form compds with contg NS, KCIO~ & DPhA) 75)C. E. Taller,USP
metals used for casings; and its priming action 1462093(1923) & CA 17,3101(1923) (Primer cornpns
is higher than that of MF or LA but its action is are formed of NS in granules of av size in excess
less brisant] 62)W.C.Cope,I.JSP 1399104(1922) & of 0.045 mm, together with KCIO~ & DPhA)
CA 16,833(1922) (An initiating compn adapted for 76) Etablissements Davey,Bickford, Smith et Cie,
ignition by flame or elec spark is made of MF 80, BritP 196593(1923) & CA 17,3791(1923) (LA for
Pb304 5-20 & KC103 5-15%) 63)W.M.Dehn USp use in primers is desensitized by the addn of 0.05
1404687(1922) & CA 16,1154(1922) (DADNPh is -20% by wt of oils, greases or paraffins) 77)E.I.
mixed with KC103 or other oxidizing salt to form duPont & Co, BritP 204646(1923) & CA 18,905(1924)
an initiating compn) 64)H.T.Peck,USP 1407767 [PETN in priming compns for igniting proplnt expls
(1922) & CA 16,1669(1922) (TNR, together with Eg: PETN 5-10, KC103 50, Pb(SCN)2 25-23 &
MF, ground glass, KC103 or other ingredients, is Sb2S3 20-17%; Or PETN, KC103, MF & Sb#a]
used for charging primers) 65) R.M.Cook & B. 78)B.Grotta,USP 14836(1924) & CA i8,905(1924)
Grotta,USP 1406977(1922)& CA 16, 1669(1922) (A base chge of detonators is made of ground,
(HNDPhA together with primary detong compds smokeless proplnt mixed with Tetryl, TNX or
such-as MF & KC103, is used for charging caps) similar aromatic nitro compds) 79)E .von Herz,
66)H.Rathsburg & W. Friederich,BritP 195344 BritP 241,892(1924) & USP 1625966(1927); CA 20,
(1922) & CA 17,3609(1923) (Basic salts of 3574(1926) & 2 1,2065(1927) (Salts of isonitramines,
Tetrazole and its derivs are used singly or mixed for use such as Pb methylenediisonitramine in
together for use in primer & detonator compns) ietonator compositions and other ingredients may
 B 193

bepptdsimultaneously with them) 80)c.I.B. & CA 22,3780(1928) [A solid defgrg oxide of C

Henning,USP 1473818(1924)&CA ]8,472(1924) (“graphitic oxide’) is mixed with MF,TNT,PA,
(HNDPhA3 when used with KC103, Sb2S3 & Ph- etc to obt a primary mixt for expls] 96)0. Turek,
(SCN), , is suitable for use in primers which BritP 308781(1928), GerP 494289(1928) & USP
ignite w/o deton when lightly struck) 81)W, 1824848(1932); CA 24,502,2886(1930 & 26,309
Friederich,USP 1478429(1924)&CA 18,905(1924) (1932) [A detonator contains a base chge of highly
[Basic Pb Hexanitrodinitroresorcinate, Ce(NOz)~02- compressed TATNB(Triazidotrititrobenzene), TNT
(Pb.0H)4, or other tryst basic or double salts are or Tetryl and a top chge of TATNB 10 aded at a
used with the usual ingredients for prepg priming press not exceeding, 300kg/cm2 ). LA may be used
mixts for expls] 82) E. M.Symmes,USP 1480795 together with TATNB as the top chge]
(1924) & CA 18,905(1924)( TNB is used, together 97)Werkzeugmaschinenf abrik Oerlikon,BritP
with various other ingredients, in initiating compns) 309114(1928) & CA 24,502(1930) (Primers are
83)E.Har16,USP 1488787(1924)&CA ]8,1911(1924) formed with a primary chge of KC103 & Sb2S~
[LA, mixed with 0.05-20% of fatty or similar sub- with or w/o MF, a secondary chge of LA, and a
stance(12-14% paraffin), forms a desensitized prim- tertiary chge of TNT, Tetryl or PETN)
ing compn which retains its power undiminished] 98) H. Rathsburg & E.von Herz,BritP 310509(1928)
(Compare with Ref 76) 84)J.M.Olin,USP 1495350 & GerP 518885(1928); CA 24, 728(1930) & 25,
(1924) & CA 18,2252(1924) (Ferro-Si with Ml? & 3487( 193 1) [Mixt of LSt & Tetracene with or w/o
KC103 in priming compns) 85)J.B.Smith,USP Ba(N03 )2, Sb2Sa or si!icides is proposed as a
1502754(1924) & CA 18,2964(1924) (A detonator or primary’ compn. Another example: LSt 25-55,
blasting cap contains as a base chge, PA mixed Ba(NO~ )2 24-25, Pb02 5-10, Tetracene 0.5-5,
with TNT. MF is used as a primary chge) 86)C.I. Sb2S~ 0.10, CaSi2 3-15 & glass powd 0/5%]
B. Henning,USP 1503530(1924) & CA 18,2964( 1924)[A 99)E.M.Symmes,BritP 333534(1928) & CA 25,
rnixt which is easily detonated is comprised of 595(1931) (DADNPh is mixed with LA as a
TNB, KC103, MF or Pb(SCN)2 & SbzS~] primary chge above a base chge of Tetryl, TNT
87)H.Rathsburg, USP 1511771(1925) & USP 1580572 or PA) IOO)K. F. PauI, BritP 333539(1928) & CA
(1926); CA 19,178(1925) & 20,1907(1926) (Same as 25,595(1931) (DADNPh is used in blasting detona-
Ref 57) 88)C.A.Woodbury, USP 1518629(1925)& tors with or w/o KCIOe, KC103 or NH4C104 as
CA 19,578(1925) [Blasting detonators are made oxidg agents in either the top or base chge. Other
with a base chge of ground pyre-NC (100% thru 30 compds such as Tetryl, TNT or PA may be used
-mesh sieve and 35-90% thru a 100 mesh sieve) and as base chges with DADNPh as top chge)
a primary detong chge of MF & KC103] 89)B. Grotta, 10l)J.Piccard,BritP 340971(1928) & CA 27,2303
CanP 246338(1925) & CA 19, 1349( 1925)(A compn (1933) (DADNPh may be used in admixt with 20
for detonator contains MF, HgN~ & TNT) 90)B. -80% of Tetryl, TNA, TNT or MF as a chge of
Grotta,USP 1533798(1925)&CA 19, 1778( 1925)( The blasting caps) 102)J.D.McNutt,USP 1718370
base chge for a compd detonator consists of a mixt (1929) & USP 1755330(1930); CA 23,4974(1929)&
of equal amts of Tetryl & NH4C104 or KC103, while CA 24,2886(1930). (A non-corrosive priming compn
the primary chge is of MF & a heavy betal azide) is made of MF, Ba02 & Ca silicide or MF, Ba(NO~2
91)W.Friederich, USP 1552836(1925) & CA 19,3596 & DPhA) 103)Hercules Powder Co, FrP 675638
(1925) [A priming mixt suitable for general use ( 1929)& FrP 676933(1929); CA 24,2886 & 3115
with expls is prepd by pouring solns such as of (193 O)(A priming chge for blasting caps contains
NsN9 & Na picrate into solns such as of Pb(NQ3 >] DADNPh 20-80 & LA 80-20%. This mixt may be
92)H,Rathsbrug,USP 1588277(1926) & CA 20,2751 used above a chge of TNT or PA) 104)W. Eschbach
(1926) (Tetracene is used with chlorates, nitrates, & W. Friederich,BritP 343485( 1929) & GerP 605840
peroxides, etc to form an expI primer compn) (1934); CA 27, 2303 (1933) & 29, 1988( 1935) [Mixt
93)Remington Arms Co, BritP 285232(1927)& CA of PETN(phlegmatized with paraffin, stearin or
22,4821( 192s) (A priming mixt w/o percldorate is beeswax) and NC(gelatinized with NG, NGc, Nitro-
made with MF, Ba(NO~ )2, Pb(SCN)2 & Sb2S9 ) polyglycerinol or the like) is compressed at ca
94)Nobel’s Explosives Co Ltd & G. Morris, BritP 800kg/cm2 to form a chge for detong caps]
297853( 1927) & CA 23, 2827( 1929) [Detonators 105) E. I.duPont,GerP 564584(1930), BritP 350036
for blasting purposes are provided with a high d (1929); CA 27,1177 & 2304(1933) [An expl filler
base chge of PETN Or a rnikt of Tetryl & TNT for elec detonators contains MF or LA and a
(loaded in moIten conditiom) and a priming chge mixt of Pb(SCN)2 30-50, KC109 10-30 & smokeless
of LA & LSt] 95)A.W.Schorger,USP 1681259(1928) proplnt 30-50%, as ignition chge] 106)W.deC.

1
 I

B 194

Crater,USP 1759565( 1930) &USP 1887290( 1933~ 26,4177(1932) & CA 27,3080,3612(1933) [Tetracene
CA 24,3649(1930) & 27,1513(1933) (A blasting cap with DA13NPh, Pb(N03 )2, Pb(SCN)2, LSt & glass
chge is composed of tryst Nitrolactose as a base is used as a priming compn](compare with Ref 92)
ch~ with AIF & KC103, LA or DADNPh as primary (See also USP 1991731(1935)&CA 29,2360( 1935)
chge) 107)E.von Herz,FrP 683345( 1929)& USP and USP 2038097( 1936) & CA 30,4010( 1936)]
1878652(1933); CA 24,4636(1930)& 27,420(1933) 118)] .E.Burns,USP 187862(1933)& CA 27,420
[An intermediate chge for detonators maybe made (1933) [2,6-Dinitroquinone-2-diatide is used with
of HNMnt or of its mixt with PETN (in mol propor- Pb picrate, Pb(N03 )2, Pb(SCN)2, gum arabic &
tions) and an ignition mixt of hlg & Al with oxidg glass as a priming chge] l19)L.H.Fisher, USP
substances which may contain metallic(such as 1890112(1933) & CA 27,1758(1933) (An igniter
Pb) hypophosphite] 108)J .D.McNutt,USP 1774992 chge for blasting caps is composed of K3 FeC6NG
(1930) & CA 24,5160(1930) (An expl priming mixt 20-40, KCIO~ 10-30 & NC 70-30%) 120) J. D. McNut t ,
comprised of Pb02, Ba chromate, MF & Tetryl ) USP 1906394(1933), USP 1930653( 1934) & USP
109)D.T. Jones et al, BritP 328277(1930) & CA 2002960(1935); CA 28,328(1934) & 29,4944(1935)
24,5499) (1930) [Caps chged with one or more basic [Pb dinitrophenylazide is used with Ba(N03 )2 and
normal or acid salts of 2-mononitroresorcinol various other additives to form an expl priming
which may be used with LSt, and to this may be compn. It is also used with Ag Tetracene, with
added] B a(N03 ) or PETN] 110)J .D.McNutt,USP Pb02, Ba(NO~ )2, gum & Sb$s, and with LSt plus
1779820(193 l),USP 1779821(1931), USP 1779851 other ingredients] [See also USP 2005197(1935) &
(1931), USP 180023(1931)& USP 1825466(1932> CA 29,5274(1935)] 121)G.A.Noddin,USP 1906869
CA 25,208,3487,5564 & ~6,309(1932) [Priming (1933) & CA 27,3612(1933) [An elec blasting cap
mixts are composed of the following ingredients: is primed with LA covered with a layer of loose
Pb02 20-40, Ba(N03 )2 3-10, MF 30-45 & PETN mixt of Fb(SCN)2, KCIO~ & ground pyre-NC]
3-15%; Ba(N09 )2 >40, MF ca 35, Pb(SCN)2 ca 122)H.A.Lewis, USP 1918920 (1933) & CA 27,
16, BaC03 2 & charcoal 2%; MF(contg 16% H20) 4931( 1933)[A blasting cap contains TNT as a base
475, Ba(N03)2 240, Sb2Sa 255, TNT 30& DPhA chge, LA as a primary chge and a top layer of
0.5-2p; or basic Pb nitrate, MF, Pb(SCN)2 gum Pb(SCN)2, KC103 & ground pyre-NC] 123)S.B.
arabic & ground glass] 11 l)Ziindhutchen- und Large, USP 1928204,5,6 & 7(1934) & CanP
P atronenfabrik vorm SeHier & BeIlot und Frantisek 341781(1934); CA 28,328 & 5242(1934) (Compd
Bletcha, Austrian P 126150(1931) & CA 26,2320 detonators for expls consist of the following
(1932) [An initiating compn consists of a colloidal chges: a primary chge of HNMnt & a base chge of
ppt of AgN~ or HgN3 which is mixed while moist Tetryl; a primary chge of H NMnt with a fuse head
with substances such that the mixt can be gran- of KC103 & MF; a primary chge of HNMnt & nitro-
ulated and dried. Additives may include kieselguhr, Iactose; or a primary chge of Nitrolactose alone)
asbestos, KN03, Ba(N03 )2, KC103, PA, MF or 124)J.E.Burns, USP 1928780(1933)& CA 27,598
Sb2S5] l12)P.R.Aaronson, USP 1826714(1932) (1933) (Pb salt of dinitrosalicylic acid is used,
& CA 26,601(1932) [ A priming mixt for expls con- with MF or other additives, as a priming chge)
sists of MF, Ba(N03)2 & Cd peroxide] 113)J.D. 125)J.Meissner, USP 1930765(1933) & CA 28,328
McNutt, USP 1842556(1932)& CanP 319719(1932)) (1934) (Chges for detonators consist of LA as
(A priming mixt consistg of Pb02 20-40, Ba chrom- nrimarv and TNT as base ch~e) 126)M. F. Biazzi,
ate-5-10, MF 25-40 & TeNA 3-15% or MF 40, Ba(N03 )2 ~~~tp-~87545(1933) & USP l~50019(1934); CA28, ”
29, Pb(SCN)2 10 & an abrasive 20%) 114)A.S. 328 & 3235(1934) [Blasting detonators comprising
O’Neil & A. G. Schuricht, USP 1849355( 1932)& CA a base charge( such as an aromatic nitrocompd)
26,2867(1932) (An expl contg NC & TeNA in col- separately compressed in an Al case, surmounted
loidal form, can employ a cap contg TeNA, or with a primary chge compressed in a small cap
TNT as a base chge and MF as priming chge) either of Cu(if MF is used) or of Al(if LA is used)]
115)J.D.McNutt, USF’ 1851398(1932) & CA 26, 3114 127)W.deC.Crater, USP 1951595(1934) & CA 28,
(1932) [An expl priming mixt contains MF 45, 3590( 1934) (Inositol nitrate as a chge in blasting
basic Pb nitrate 8, Ba(N03)2 30, Sb2S3 5, Ca caps) 128)J.Piccard,USP 1964077(1934) & CA
silicide 4 & Pb(SCN)2 8%] 116)E. von Herz, USP 28,5242( 1934) (A flash compn for use in blasting
1859225(1932) & CA 26,3923(1932) [LSt is used caps is formed of dimethylpyrone methyl perchlor-
with Ca silicide or MF, Pb02 & Ba(N03)2 as a ate, KCIO & AgNOq, with an NC binder added)
priming chge] l17)J.E.Burns, USP 1862295(1932) 129)H.A.~ewis~CanP 340569(1934) & USP 1964825
usP 1900157 (1933) & uSP 1905795 (1933); CA (1934); CA 28,4235 & 5242(1934) [An ignition
 B 195

compn, as the top chge in a blasting cap, contains Ba(NOa)2 40, MF 25 & Sb2S3 25%] 140) J. D. McNutt,
Pb(SCN)2 30-70, KCIO~ 30-60 & S 1-20%; the BritP 432096(1935) & CA 30,618(1936) (Alkali or
primary chge is LA] alkaline earth salts of dinitrophenyl azide are used
130)A.WeaIe,USP 1969246(1934) @ CA 28,6313 in priming compns) 141)J .D.McNutt,USP 2004505
(1934) [A priming compn for expls is made of Pb02 (1935) & USP 2009556( 1935> CA 29,5274 & 6430
with a small proportion 1-5%) of a catalyst such as (1935) (Tetracene & LA are used together or with
hln02, V2 05, M0203, Na tungstate or their mixts] various other substs such as Pb02, Sbzss, Ba(N03 )2,
131)W.Briin, USP 1971029, -30& -31(1934)& USP Ca silicide or DADNPh) (Compare with Ref 117)
1991730( 1935); CA 28,63 14( 1934)& 29,2360(1935) 142)W.Brun,USP 2004719 (1935)&CA 29,5274(1935)
(Compds suitable for use in priming compns are [About I-5% of the CUNH4 salt of diazoaminoterra-
the basic Pb salt of 3,5-DNBAc, the basic Pb salt zole is used with an initiating mixt of LSt 30-50,
of 3-nitrophthalic acid, and Pb dinitrobenzoate Pb(N03 )2 25-40, Pb(SCN)2 5-15 & an abrasive
nitroate or the nitroic Pb salt of TNBAc. The basic 10-20% to form a priming compn] 143 )C.P.Spaeth,
Pb salt of 2,4-DNBAc may be wed together with USP 2007223(1935); CanP 35333X 1935)& USP
MF, Ba(N03 )2 & an abrasive) 132)W.Eschbach & 2031677(1936); CA 29,56608336(1935)& 30,2388
W. Friederich,BritP 417763(1934) & CA 29,2744 (1936) (An ignition compn for the top chge in
(1935) (A detonator, free from hfF, is of Al, CU, blasting caps contains NC impregnated with NG
brass or Zn casing contg a base chge of PE TN or & KC103, The base chge consists of smokeless
other usual chge and a priming chge of a mixt of proplnt 40-80, NG 3-35 & KC103 2-25%) 144)G.H.
LSt or dibasic picrate with 10-20% of Hg, Ag Jacobs,USP 2027825(1936)&CA 30,1564(1936)
and/or Cu azide added in aq suspension) 133)A. [About 2-30% of Zr powd is used with Ba(N03 )2,
Weale, CanP 348291(1935) & CA 29,3518(1935) Pb chromate, Pb(SCN)2, MF & ground glass as
[A non-corrosive priming chge is comprised of a priming mixtl 145)E.I.duPont, BritP 451668
h4F 20-45, KB a nitrate(double salt) 30-60 & Pb- ( 1936) & CA 31,5 42( 1937) [Blasting detonators
(SCN)2 10-40%] 134)P.G.Wri~tsman, USP 1975186 are made of Al or high Al alloy and are charged
(1934) & CanP 348643( 1935); cA28,, 7536(1934)& with Pb(SCN)2 50, KC103 40 & S 10%] 146)w.o.
29, 3518(1935) (A cast expl suitable as a base SneHing,USP 2067213(1937) & CA 31, 1616(1937)
chge for blasting caps is made of a fused mixt of (Finely divided hfF or LA is mixed with natural or
Trinitrophenylethylnitramine (TNPhEtNA) and synthetic rubber or rubber substitute as an expl
either Tetryl or PETN or both. One example con- suitable for detonators) 147)L.Rubenstein & ICI,
tains TNPhEtNA 40, Tetryl 40 & PE TN 20%) BritP 473146(1937) & CA 32, 1934(1938) [Low ten-
135)C.P.Spaeth, USP 1984846(1935) & CA 29,1251 sion elec blasting detonators contain a primary
(193 5)(Tetrameth ylene diperoxide dicarbamide, initiating chge and a superimposed loose defgrg
alone or with various admixts, as an ignition top compn. The defgrg compn is made by coming 90ps
chge for elec detonators) 136)H.A. Lewis,USP of basic Pb salt of 3,5-dinitro-2-hydroxytoluene
1991857(1935) & CA 29,23,60(1935) (A blasting cap (contg 58% Pb) with 10ps KC103 with the aid of
of Al contains LA placed nearest to the closed end l-2ps acacia gum in 60ps HZO; the primary chge
of the tube and a secondary chge of TetryI) consists of lg of 80/20 MF/KC103 mixt] 148 Poe-
137)ICI, FrP 781646(1935)& FrP 796833(1936} d’Exploitation des Brevets O. Matter,FrP 818285
CA 29,6430(1935) & 30,6200(1936) (A compn which (1937) & CA 32,2358( 1938) (A priming compn con-
is ignited directly by an elec current is comprised tains MF 65, Ba(N03 )2 22, SbzS3 11, RDX 15.5 &
of a mixt of Zr powd 70 & Pb mononitroresorcinate BaCO~ 1.5g) 149)L.Rubenstein & ICI, BritP
30% in a sufficient amt of a 5% soln of NC in amyl 470418 (1937) & USP 2125462(1938); CA 32,1456
acetate to make a creamy paste) 138)C.E .Sosson & 7728( 1938) (A blasting cap contains a base chge
& ICI, BritP 428872(1935) & USP 2027208(1936); of Guanylazide picrate with or w/o other base
CA 29,7078(1935) & 30, 1564(1936) (An ignition chge expls such as Tetryl and a primary chge of LA,
compn for low tension elec blasting fuses is made with or W/o LSt. The detonator case shall be of
of finely divided Zr 35-39 & the basic Pb salt of Al and have an elec fusehead primed with Pb mono-
2-mononitroresorcinol 65-6 1%; the mixt may be used nitroresorcinate. Alternatively, the primary chge
loose or agglomerated with an NC cement. For use may be MF and the detonator case of CU or CU
in delay detonators a mixt of Zr 50-95 & the Pb alloy) 150)L.H. Fisher, USP 21045 13(1938) & CA
salt 50-5% is used) (Compare with Ref 137) 32, 1935( 1938) [An initiating expl for blasting cap
139)G.H. Chambers,GerP614712( 1935) & CA 29, consists of DADNPh & Ba(NO~)2] 151)P.W.
8335(1935) [A priming cornpn contains 7X powd 10, Schuster,GerP 6553 18(1938)& CA 32,2754(1938)
 I

B 196

[A blasting cap contg a self-igniting chge composed DADNPh & KC103 or of DADNPh & NC or NS)
of KC103 & a solrr of yel P in CS2. The chge 165)G.H.Smith & C. B.van Winter,USP 2189301( 1940)
ignites when the SOIV(CSZ ) is eva~d at a controlled & CA 34,4271(1940) (An elec blasting initiator is
rate] 152)Deutsche Waffen-und Munitionsfabriken comprised of ground smokeless proplnt with S, Ca
A-G,FrP 824130(1938) & CA 32,5630(1938) (A silicide, Zr or Se and KC103, Ba02 or KN03)
priming compn, resistant to oxidn, contains LSt 16 6)H.I.Etchells, Jr,USP 2190777(1940) & Ca 34,
30-60, Diazotriazolecarboxylic acid 1-10% together 4272(1940) (DADNPh is used with Ba(NO~)2 & a
with Sb2S3, Pb02, Ba(N03 )2 & CaSi) 153)L.A. nitrated carbohydrate or smokeless proplnt as an
Burrows et aI USP 2105635(1938)& CA 32,2358 ignition compn in elec blasting caps) 167)C. E.
(1938) (An ignitiwr comp suita~~e for use in elec Pritham et al, USP 2194480( 1940) & CA 4908( 1940)
blasting caps uses Bis-triethyl pb styphnate ) (A non-corrosive priming mixt for expls is made of
154)W.F.Filbert & W. E. Lawson,USP 2118501(1938) red P, Ba(N03)2 & Sb2S3) 168)S. B. Large & G.F.
& CA 32,5630(1938) (Pb salt of the nitrated prod Rolland,USP 2195032(1940) (A detonator contg a
of diphenylol propane with KC103 or with Zr & base chge of TetryI, a primary chge of the’ safety”
NS is proposed as an ignition compn for elec type expl and an ignition chge of not more than
blasting caps) 155)C.A.’y~oodbury, USP 2118533 O. 15g DADNPh. The ignition medium serves to in-
(1938) & CA 32,5632( 1938) (Blasting caps contg a flame the primary chge but is incapable of directly
homogeneous blend of Bkpdr & ground smokeless detong Tetryl) 169)W. B. Toodring, USP 2206652
proplnt) 156)R. F.5.COX,USP 2125221(1938) & (1940) & CA 34,7610(1940) (A priming expl compn
CA 32,7728(1938) (Hexanitrodipheny lethylenedi- is made of LSt, the Pb, Na or Cd salt of Trinitroso-
nitramine as a chge in blasting caps) 157)V.J. phloroglucinol & an oxidg agent) 170)P.Naoiim,
Kelson,AustralianP 104189(1938) & CA 32,8782 GerP 698403( 1940)&CA 35,6796( 194 l)A detonator
(1938) (A primer mixt consists of MF, K dinitro- is charged with Hexamethylenetriperoxidediamine
phenylazide, KB a nitrate double salt, SbeS3 & alone or in admixt with inert substances) 171)E.I.
Pb hypophosphite) 158)J.D.McNutt, Brit; 495238 duPont,BritP 519749( 1940)& CA 36,274(1942) [An
(1938 ),USP 213680(1939) &USP 2292956( 1943);CA ignition compn for elec blasting detonators con-
33, 1500,3158(1939)& 37, 1042( 1943)(A priming mixt sists of or includes a complex or double salt of
suitable to ignite a proplnt is comprised of MF, K Pb(NO~ )2 & a Pb salt of nitrophenol] 172)W.deC.
dinitrophenylazide, KB a nitrate double salt ,Sb2S3 & Crater,USP 2214721(1941) &CA 35,898(1941)
Pb hypophosphite) (Compare with Ref 157) 159)Wm. (A base chge of PETN with a superimposed prim-
H. Rinkenbach & H. Q. Aaronson,USP 2167679(1939) ing chge of DADNPh is used in blasting caps)
& CA 33,8992(1939) (Dinitroethylurea is used alone 173)W.Briin,USP 2239547(1941) & CA 35,4956
or with other materials in blasting caps or as the ( 1941) (A method for prepg priming mixts involves
booster chge) 160)Dynamit A-G, BritP 510992(1939) mixing Ba(N03)2, glass pdr, moist Styphnic
& CA 34,5664( 1940) (An all-purpose priming compn Acid & moist basic LSt; the mixt is maintained
is made by causing salts of Tetrazylazide to react in moist condition so t~at normal LSt is form-
with chlorides, sulfates or nitro compds or org ed by reaction of moist styphnic acid and
substances in soIn. The usual priming constituents basic LSt) 174)R.W. Lawrence,CanP 398139(1941)
may be admixed with the product) 16 l)L. A. Burrows CanP 398865( 1941), BritP 546276(1942) & USP
& W. F. Filbert,USP 2175249(1940) & CA 34,888 2350172(1944); CA 35,6796 & 7716(1941) & 37,
(1940) (An ignition chge in the form of a bead sur- 3274(1943) (An elec blasting cap.resistant to deton
rounding the bridge wire for an elec blasting initia- by external heat contains a priming chge of LA &
tor of the delay type is made of a complex Pb ni- a secondary chge of PETN, 30-60% by wt of the
trate salt & bis basic Pb picrate) 162)W.Briin, priming chge. In a later device, a protector unit, at
USP 2175826( 1940) & CA 34,887(1940) [An expl least 0.01” thick, of TNT or p-nitrobiphenyl is
priming compn is prepd by moistening(v# dis solv- placed between the metal casing and the detong
ing) a mixt of Pb or Ca nitrate with a hypophosphite expl to desensitize the chge to external heat)
of K, Na, Ca, Si, NH4, Ba or Mn] 163) E.B.w. 175)E.von Herz et al,GerP 708238(1941) & CA
Kerone & C. C. Carroll,USP 2177657(1940) & CA 37,2938( 1943) (A priming compn, sensitive to flame,
34,1 176(1940) [Basic Pb nitroresorcinol salt with impact or friction, is made of a mixt of a nitrate, a
MF or LA, Ba(N03 ~ & other ingredients is used tetra-, penta- or hexahydric alcohol, Tetracene &
in primers] 164)H.E.Nash,USP 2186426& 7( 1940) a powd metal of good thermal conductivity)
& CA 34,3498(1940) (An elec blasting cap contains 176)L.A. Burrows & G. A.Ncddin, USP 2268372
a detong chge and an igniter chge comprised of (1942) & CA 36,2726( 1942) (In an ignition compn
 B 197

for elec blasting caps, use is made of a loose of Pb hypophosphite & basic and normal LSt in aq
chge of colloided smokeless proplnt & ca 15-25% soIn at 70° ) (Compare with Ref 158) 187)George
of Pb 4,6-dinitro-o-cre sol) 177)F .M.Garfield,USP A. Lyte,USP 2360698( 1944)& CA 39,1294(1945)
2295104(1943)&CA 37,1272( 1943) (Cryst double (A blasting cap is filIed with 3 separate charges:
salts of normal LSt & Pb acetate or Pb propionate initiating chge - <0.10g LA; secondary chge -
are proposed for use in blasting cap ignition or 0.25-O.35g of LA & TNT; and main chge-PETN
priming charges) 178)L.A.Butrows, CanP411441 & TNT) 188)E. J.Hanley,USP 2363863(1944) &
(1943), CanP 411756(1943)& USP 2427899(1947); CA 39,3672(1945) (An initiating expl for secondary
CA 37,3607 & 3943(1943) & 42,764(1948) (A blast- expls is comprised of LA 60-95 & BkPdr or
ing initiator contains a base chge of HNMnt and a smokeless proplnt 5-40%) 189)L. A. Burrows,CanP
top chge of DA13NPh & KCIO~; part of the top 428518(1945) & CA 39,5080( 1945) (A blasting cap
chge is disposed in a ~avity in the base chge. A contains a base chge of PETN and a top chge of
later device contains a detong expl base chge, a DADNPh & KCIO~; at least part of the top chge is
LA primer chge and an ignition chge of Tetryl disposed in a cavity in the base chge) 190)G.F.
30-70 & LSt 70-30%; dead-pressed HNMnt is RoHand,USP 2388368(1945) & CA 40,1036(1946)
placed between the ignition and primer chges) (An ignition compn contg cuprous acetylide or
179)SFMCTG,FrP 881262(1943) & CA 47,8374(1953) other metallic acetylide, is prolonged in sensitivity
[Guncotton mixed with Pb02 (60%), Pb304(65%) or life by incorporating up to 5% of abietic acid or
KMnOa (50%) produces compns suitable for use in rosin) 191) E. I.duPont & L. A. Burrows, BritP
igniters of elec primers. Changes in sensitivity or 568109(1945) & CA 41 ,2900(1947) (An initiating
ignition props can be obtd by adding Sb2S~ or C & compn is produced by mixing trysts of DADNPh
KC103 or KC104] 180)SFMCTG,FrP 893941(1944) & HNMnt with a SOIV miscible with w but in
& CA 47,8374(1953) (Mixts of usual priming agents which HNMnt is sol and DADNPh is insol)
with expls to increase the vel of deton are describ 192)L.A.Burrows, USP 23961 52(1946) & CA 40,
ed. Typical compns are: Trinitroazobenzene, PA 3606( 1946) (An initiating expl compn for loading
& Urea Picrate or Tricycloacetone peroxide, PA blasting caps consists of a base chge of PETN
& RDX. A still higher vel of deton is achieved by and a priming chge of DADNPh & HNMnt. When un-
using a plastic tube of NC & BkPdr to replace confined, this priming chge burns w/o expldg)
tubes made of Cu or brass) 181)L.R.V.Clark, 193)G.U.Graff,USP 2395045(1946) & CA 40,3608
USP 2326008(1944) & CanP 435873(1946); CA (1946) (A priming compn for initiating LA is prepd
38,488( 1944) & 40,6818 (1946) (An initiating chge from amixtof PbOz, Ca silicide,Zr&S; Mn02 can be
of Pb nitroaminoguanidine is superimposed upon used to repI ace part of the Pb02) 194)W.M.Cobb,USP
a base chge of PETN as a fuse or blasting cap 2400103(1946) & CA 40,4525(1946) (A substantial-
compn) 182)G.M.Calhoun, USP 2327867(1944) & ly spherical blasting cap contg a base rhge such
CA 38,867(1944) [Ammunition priming compns are as Tetryl, PA, PETN or TNT will deton consist-
made of Pb hypophosphite 8-10, Pb(NO~ )2 10-12, ently if heat is applied by thermite, composed of
LSt 28-33, Ba(NO~)2 14-23.5, glass 30 & LSt Mg powd or Ba02 & an oxidg agent. Thus, the
0.5-2%] 183)W.Brun,USP 2341205(1944) & CA usual extremely sensitive priming chge is eliminar
38,4448( 1944) (Mixts of Tetracene, LSt & PA are ed) 195)L.A. Burrows & W. E. Lawson,USP 2402235
used in various priming compns) 184)W.Briin & (1946) & CA 40,5568( 1946~Blasting caps are made
L. A. Butrows,USP 2341263(1944) & CA 38,4448 less sensitive to shock & frictional impact by
(1944) [Ammunition priming mixts are made of MF, blending with the primary chge a small quant(O. 5
Ba(N03 )2 & Hexamethylenetriperoxy diamine (as -3%) of Ca stearate in finely divided condition]
sensitizer) 0.5- 10%; other ingredients may be 196)W.W.Vogl,USP 2406573(1946) & CA 41,286
added] 185)P.H. Burdett & G. M. CalhountUSP (1947) (An expl suitable for loading detonators,
2345868(1944) & USP 2350670( 1944); CA 38, fuses, boosters or shells is prepd from ethylene-
4806 & 5086(1944) [An ignition priming mixt diamine perchlorate by forming ad addn compd
is prepd from normal Pb 3. 5-dinitrobenzoate 8, with PA)
LSt 40, Tetracene 2, Pb(N03 )2 30 & glass pdr 197)L.F.Audrieth, USP 24108O1(1946) &CA 41,
20%. Also the acid Pb salt of DNR (1-15%) is used 866( 1947) [A non-fulminating primer mixt contains
together with the same materials] 186)J .D. McNutt KC103 51, Sb2S3 34, (SCN)X 10 & LA 5% or
& S.D.Ehrlich,USP 2352964(1944) & CA 38,6098 KC103 64, Sb2Sa 21,(SCN)X 10 & LA 5%1
(1944) (A complex salt suitable for use in detona- 198)C.Franqais,FrP 856366(1946) & CA 42,2774
tors or primers is made of equimolecular proportion (1948) [A non-corrosive initiating mixt consists
 B 198

of MF 38,” Ba(N03 30, Sb2S3 15, CaSi2 10 & glucose polyanhydride) 208)W.A. F ilbert,
Pb02 7%; the Pb02 & CaSi2 may be replaced by USP 2511669(1950) & CA 44,9149( 1950)[Ignition
RDX] 199) J. D. Brandner,USP 2415001( 1947) & compn which is characterized by short delay
CA 41,2578( 1947) [Diisopropanolamine trinitrate between ignition & full flame, is comprised of
(mp 119.6°) is a secondary HE particularly BkPdr(KN03 74, charcoal 15.6 & S 10.4%)
suitable as a base chge in compd detonators. It accelerated by 5-10% of a double salt of Pb(N03)2
is highly resistant to shock or friction but is & a dibasic Pb salt of 4,6-dinitro-o-cresol. A
readily detonated by primary expls] 200)C. J. primary ignition chge suitable for elec ignition
Bain & L. R. Carl,USP 2415806(1947) & CA 41, of the accelerated Bkpdr consists of the fore-
2901( 1947) (Compd detonators for use in am- going Pb salt 72, KC103 18 & NS 10%] 209)R.
munition contain a main chge of a nitrocompd, W. Cairns & R. W. Lawrence,USP 2525397(1950)
a primary chge of LA and an’ igniter of Sb.#3, & CA 45,4043( 1951) (High density blasting
KC103 & LA) 201)G.F.Rolland,USP 2422043 gelatin may be detonated at high vel through
(1947) & CA 41,5725 (1947)(A compd detonator the use of a blasting cap having a base chge of
contains a base chge of PETN and a superimpos- expl energy e quiv to PETN at d 1.45, provided
ed initiating chge of 75 DADNPh & 25% HNMnt) that the closed end of the cap weighs no more
(Compare with Ref 192) 202)0 .A. J. Gurton & than O.lg) 210) F. Habbel,GerP 803644(1951) &
I. O. Lewis, BritP 787346(1947) & CA 52,6796 CA 45,5930(1951). (A detonator cap having an
(1958) (Ventless delay elec detonators with elec ignition device in which the usual priming
reduced tendency to ignite mixts of air & CH4 compn of LSt 20 & LA 80% is replaced by LA
are made, by pressing 0.25g of a PETN or alone) 211)H.Elsner,GerP 803645(1951) & CA
Tetryl base chge into a std No 6 CU Cap; 46, ~26q1952) [Detonators are made safe for
followed by pressing 0.35g of LA or AI/LA/LSt use in the presence of fire-damp by mixing
mixt thereon and “then inserting a tightly fitting from 3 to 20% of an inert material such as KC1,
brass tube, the bore of which has a free air Na2COa, NsHC03, KBr or wax with both parts
,,
space ca 0.08 long adj scent to the primary of the detonator chge. This chge may consist
expl. A delay compn of Si & Pb02 or Sb & of a primary chge of MF, LA or LA 65 &LSt35%;
KMn04 is used to provide delays of 35-332 and a secondary chge of PETN or Tetryl. Poly-
millisec) 203)L.Rubenstein & B. CompbeH, carboxylic acids or their salts(up to 20%) may be
USP 2464777(1949) & CA 43,6828(1949) [Addn added to the secondary expl to improve the fire
of 4-12% NC(having a fiber length of 30-250p) -damp safety of blasting caps] [See also GerP
to LA reduces its sensitivity & improves its 919156(1954) & CA 52,14172(1958)] 212)T.
loading characteristics for use in detonators] Sakamaki,JapP 147(1951) & CA 46,11690(1952)
204)E.J.Hanley,USP 2476370(1949) & CA 43, (Pb or Ag salt of dinitroresorcinol contg 5% of
8683( 1949) (An ignition compn for rocket proplnts collodion as a binder, or a mixf of Pb dinitro-
and other expls comprising Pb 57.8, Se 22.1, Al resorcinate 55, KC104 20, S 10, Al powd 10 &
2.55, Mg 2.55 & KN03 15%, is prepd by mixing collodion 5% is used in an elec blasting cap)
the dry powdered components. This mixt is 213)J.F.Kenney,USP 2589703(1952) & CA 46,
pressed into std Al or Zn caps over a Mg-KN03 5320(1952) [A new tryst form (cubic) of LSt
flash chge) 205)’W.N.King,USP 2480141(1949) suitable for use in primers & detonators is
& CA 44,841(1950) [A mixt-more stable at high described. The new form is claimed to be less
temp & high humidity than std MF primers, con- sensitive to static elec and compns contg it have
tains basic LSt 40, B S(N03)2 42, Sb2Sa 11, zreater and more uniform im~act sensitivity &
NC 6 & Tetracene I%] 206)W.D.Trevorrow, improved burning characteristics] 214)S.D.
USP 2484131(1949)& USP 2487906(1949); Ehrlich,USP 2597926(1952) & CA 46,7771( 1952)
CA 44,2247 & 7540 (1950) (Gelling of ignition (Substantially uniform wts of PETN, contg
mixts, prior to application trr the igniting 0.25-4 .0% of finely divided graphite, can be
element, is prevented by addn of a monohydric charged into detonators whereas in the absence
alc or acet, up to 20?4 by vol of the nitrocarbo- of graphite varying wts result. , Also, the
hydrate-solv portion. The ignition mixt is com- graphite reduces the tendency of PETN to ad-
posed of Pb salts of nitrophenoIs & NS or NC) here to surfaces with which it comes into con-
207)J.T.Power,USP 2495868( 1950) & CA 44, tact) 215)C.P.Spaeth & C. P. Williams, USP
7540(1950) (A detonator contg a base chge of 2607672(1952) & CA 47,4048(1953) (A stable,
nitrated dextrose polymer, such as nitrated gasless, ignition or delay compn for use as a

———. , .— .—
 B 199

loose chge in elec blasting caps consists of 25, Ca siIicide 20, Ba(N03 )2 24& Pb02 6%;
Bi 48, Se 47 & KCIO~ 5% and Bi 61, Se 36 & gum arabic, 0.5%, is used as a binder)
KC103 3%, all as 200-mesh powds) 216)Soci4t6 224)G.A.Noddin & C. P. Spaeth,USP 2717204(1955)
Alsacienne d’Explosifs et ~Applications & CA 50,2174(1956) (An initiating chge for use
Chimiques,FrP 1023552(1953) & CA 52,3346 in elec blasting caps is made of grained red P
(1958) [A friction detonator for expls contains 99 & amor B 1%. Such a mixt is claimed to be
a nylon cord with a pearl on its en’d encased in a readily ignitable and to have a controlled rate
sheath of an abrasive paste(50g glass powd, 20g of combustion) 225) J. F. KenneyUSP 2728760
KCIO~, 7g gum & 3CC w). On drawing out the (1955) &CA 50.7462(1956) [The K salt of 2,4
cord its end passes through a pellet(constg of -dinitro-6-(tetrazeno)-phenol (a dk-red tryst ppt
Sb2Sa 40, KN03 45, MF 10 & gum 5%) that which dec explosively at ca 200°) is proposed
forms part of the detonator. TIE pearl assures as an ingredient of priming cornpns] 226)T.
an ultimate energetic friction of the sheath Toshima & K. Honma,JapP 5098(1955)& CA 51,
material which ignites the pellet] 217)W.J .H. 17170(1957 )[A delay compn for millisec delay
Schneider,FrP 1026869(1953) & CA 52,5826 detonators, composed of Si-Fe 15, Pb chromate
(1958 ){ Tribasic Pb picrate,[Pb(C6H2N307 ).- 5, Ba02 75 & minium(Pb304 ) 5%, has a rate of
3 P“bO. 2. 5H20], is proposed as an igniter; its combstn of 0.2 see/cm in air] 227) J. Prior,GerP
expln point is 160-180° and ,igraition delay 922216(1955) & CA 51,17170(1957) { Ignition or
0.6, 1.5 & 4.7 sec at 260°, 250° & 240°~ resp] initiating materials for blasting caps & fuses
218)E.Habbel & H. Elsner, GerP 889575(1953) & are made of insol complex compds of heavy metal
CA 52, 11426(1958) (Use of equal amts of salts with org hydroxyamines(such as triethanol-
DADNPh & butyl acetate, thickened with 5% amine) and acid radicals like SCN, C104, Br03
collodion cotton, in elec primers prevents & N3 in admixt with oxidg agents. Two readily
expln of CH4-air mixts in mines) 219)J .F. ignitable flame-sensitive complexes listed in
Kenney,USP 2689788(1954)& USP 2702746(1955} the patent are: [CUN(CZH40H)9CUO] SCN &
CA 49,7250 & 7856(1955) [Priming mixts contg [PbN(C2H40H)aPbO] C104 ] 228)S.Kikuchi,
a complex or double Fe .4alt of Styphnic Acid & JapP 6297( 1955) & CA 5] ,18612(1957) [Priming
hypophosphorus Acid [C6H(NOz)~02]3Fe2.- chges for elec blasting caps may contain Tetracen e,
2Fe(H2P02)3 are described. Typical compns DADNPh, Nitroguanidine, LSt, etc. For example:
contain the above double Fe salt 4, normal LSt a)Tetracene 70 & DADNPh 30%; ignition point 140°
38, Ba(N03)2 25 & Powdered glass 33%; or the & time of deton 6:9 millisec b)Tetracene 49,
above double Fe salt 5, normal LSt 41, Tetracene DADNPh 30 & NGu 21%; ign pt 131° & time of
4 & Ba(N03 )2 50%. A primer suitable for firing deton 143 millisec c)Tetracene 70, w LSt 30%;
indoors contains the double Fe salt 40, Ba(NO~ )2 ign pt 140° & time of deton 7.6-m iHisec. For
25 & Glass 35%. Here no Pb or other toxic sub- straight Tetracene ign p is 143° & time of deton
stance is used] 220)H.Wippenhohn, Gerp 919694 7.7, while for straight DADNPh they are 166° &
(1954) & CA 52,14172(1958) (The addn of 0.3-5% 9.2 millisec] 229)S.Okubu & S. Ikunuma,JapP
graphite or talc to PETN or other expl lessens 6898(1955) & CA 51, 18612(1957) (Cupric azide,
its sensitivity to friction while filling into the stabilized with polyvinyl alc or gelatin and
cover hose of detong fuses) 221)J.Barlot,FrP molded in the form of grains which dry into chips ,
1071630(1954) & CA 53,3698(1959) (Stable is used with RDX as a base chge for blasting cap
priming expls which are sens to moderate shock compns) 230)T.Toshima et al, JapP 8498(1955)
and to temps of 100-200° are prepd by mixing aq & CA 5 1,18612(1957) (An ignition delay compn,
or alc solns of nitrates of bivalent metals with composed of Ba02 83 “O, p-nitrophenylazo-2-n~phthol
aq or alc solns of N2H4. Prepn & props of Ni, 1.5, NS 1.5 & Fe oxide 15.0, ignites at 350° and
CO, Zn, Cd & Mn derivs are described) burns below 600° after a 4-see delay) 231)T.J.
222)J.F.Kenney,USP 2702745(1955) & CA 49, Mulqueeny,USP 2740703(1956) & CA 50,9742(1956)
7856(195 5) [A priming mixt is made(w/o the use [Ignition compns for blasting caps & detonators
of an abrasive) of normal LSt 36, K styphnate-Pb are made of Pb02 10-40( produced in situ) & Se
styphnate-Pb hypophosphite complex salt 10, 60-90%; less erratic firing is obtd than when these
Tetracene 4 & Ba(N03)2 50%] 223)A.0.Franz, ingredients are mechanically mixed] 232)1.0.
USP 2708623(1955)& CA 49,14326(1955) (A Lewis,USP 2749226(1956)& CA 50,13444(1956)
priming mixt for ammunition consists of DADNPh [A delay compn for elec detonators contains Pb304
20, Tetracene 5, Pb salt of ethylenedinitramine 91-5 & Si 95-9%{of Darticle size 5-20p)., Such a
 I

200

mixt, when compressed at 15tons/in2 & loaded & CA 54,,900(1960) [A retarded-action fuse for
into tubes 0.130” ID, burns at 10millisec/mm] blasting in mines is comprised of a central re-
233)R.G.Guenter, USP 2775200(1956) & CA 51, tarding Pb tube which separates the primer
3999( 195 7) (A detong device, which does not thermic chge. For example, 0.25g LA on each
req highly sensitive expls, is made of RDX 80, side serves as a primer, followed by 0.0065g of
NC 19.7 & DPhA 0.3%. The resulting compacted a heat-sens mixt of Al 50, Tetracene 25 & HNMnt
primer compn is water-resistant and stable up 25%, and then O.097g of an exothermic mixt of Mg
to 1000° F) 234)W.Friedrich, GerP 94501 O(1956) 30, Ba02 35 & Se 35% in a closed bronze capsule;
& CA 52, 15071( 1958) (Compds of Bitetrazole the result is a time lag of 17msecl 243)J.S.
with org polynitro compds are suitable expl prim- Glasby & C. R. L. Hall,GerP 1006770(1957) & CA
ers with relatively low sees to friction and high 54,18962( 1960) [A delay ignition compn is made
sens to shock & flame) 235)G. A. Noddin & C.P. of Ti metal (5-35v particle size), PbOz or pb~oa
Spaeth,(Listed in CA as C. P. Spaath) Gerp 941473 50-90%, possibly Si, B, Al or Mg(5-25%) & inert
(1956) & CA 52,15072(1958) [Primers with delay diluent(< 10%), such as NaCl, Fe203, MgO or
action which can be regulated to ca 100 millisec) CaF2] 244)Schaffler& Co, Australian 196295
consist of a mixt of B 0.5-3 & Pb304 99.5-97% (1958 )& CA52,6796(1958) [Adelayermass, for de-
with 0.5-1.570 granulating compds( such as poly- layed-action caps with a short delay time, consists of
ethylene glycols). These mixts can be stored amixt of powd Si, Pb304 & Pb02(Pb04/Pb02 ratio
even in wet & warm rooms; they show no tendency 78/22) with approx 5-10% of powd graphite as a
to se If-ignite and they burn thoroughly] 236)F .R. lubricant] 245)T.J .h!ulqueeny & F .R.Seavey,USP
SeaveY,USP 2767655(1956)& CA 5i,5424(1957) 2825639(1958) & CA 52,7704( 1958) (An expl train
(An improved plastic blasting cap is made by for elec detonators & blasting caps consists of a
incorporating lp vinyl rubber to 3-4ps resin in its RDX base chge, a LA initiating chge and an
fabric ation. These caps we loaded with pre-pel- ignition chge of loose dry MF 30-50 & ground
Ieted RDX as detonator. LA is used as initiator proplnt powd 50-70%) 246)H.M.Kerr & G. Towell,
& LSt as igniter) 237)T.G.Blake,USP 2771034 USP 2830885(1958) & CA 52,11426(1958) (Gasless,
( 1956)& CA 51,3999(1957) (An improved safety slow-burning, stable delay compns for use in
blristing cap contains Pb ethylenedinitramine delay fuses & particularly in ventless delay elec
as an initiator, either alone or with modifiers) blasting caps are made of a fuel 6.5-65 and oxidg
238)W.Maxwell,GerP 953506(1956) & CA 53, materials 35-93 .5%. Thus a mixt of Se 1.6, Si 6.2,
18488( 1959) (Nonflammable filling for safety Pb~04 36, pbCr04 35.9 & BaCr04 20.3% in a
blasting detonator chges consists of GuN 45-66, 0.125” diam fuse showed a delay of 1.76-9 .80sec
K peroxysulfate 27-45, CU2C12 6-10 & petrolatum in columns of 0.30-1.50 length) 247)M. G.
1%. Thermal decompn of the mixt initiates deton Berman et al, USP 2849300 (1958) & CA 52,21112
of safety-blasting chges but it will not ignite (1958) (An igniter consists ot 2 components: one
a CH4-air mixt contg 9% CH4 ) 239)K.Hino, et a starter mixt, the other a combustion-sustaining
al, JapP 1142(1957) & CA 53,719(1959) (Safety mixt. The starter mixt consists of AN 82-85,
delay compns for blasting caps are improved by charcoal 10-12 & K2Cr207 4-6y.; the combustion
adding Sb203 to prevent large heat evolution) mixt consists of AN 86, C 5-8 & paraffin wax
240) M. Yamada et al, JapP 6294(1957) &CA 53, 3-6%. Both components ate compressed & dipped
719(1950) [A safety delay compn for blasting in paraffin wax) 248)W.Dick,13ritP 800136(1958)
caps is composed of Cu powd(reduced with H or & CA 53,7598(1959) [Flexible detong fuses,
co>500° in the presence of Na2C03) 30, constg of a core(2.85g) of PETN or RDX & 0.15g
Pb304 70 ferrosilicon 5ps. It is claimed that of Na carboxymethylcellulose or Na alginate
sparks and flames from such blasting caps are per ft of fuse, are enclosed in a paper tube and
inhibited by absorption of alkali ions on the wound with jute & cotton yarn. A coating of
surface of the Cu powd] 241)H.Schliiter & wax or bitumen at 100° & a waterproof coating
R. Meyer,GerP 957195(1957) & CA 53,10765 of polyethylene are thenl applied] 249)H.P.
(1959) [The sensitivity of gelatinous detonators Jenkins & C. H. Shomate,USP 2865726(1958) &
(constg of collodiun cotton 0.8-2.0, TNT 0-6.0, CA 53 ,5680 (1959)[A method of controlling the
AN 40-60, woodmeal 0-5.0 & red Fe oxide 0.2%) rate of deton of primary or initiating expls such
is increased by the addn of 4.0-25% of pumice, as LA or MF through the addn of waxy materials
Si02, corundum, glass pdr or feldspar] & metal salts of fatty acids is described. When
242)H.A.Lewis & G. A. Noddin,GerP 964936(1957) more than 40% of additive is present, delay
 B 201

functioning of the chge becomes appreciable. Pb, Al, Sn, Ag, Cu, Mg or their alloys]
The following mixts, pressed at 12 tons/in2 into 257)D.T. Zebree,USP 2908559(1959) & CA
1/8” test cylinders(av column lengths of 0.901 54,2745(1960) (An elec initiating device having
.().908”), gave the following results: LA/Al a delay fuse element and a loose ignition mixt of
stearate, 57.14/42 .86( for 0.902”) 108*35 microsec Pb 72.4, Se 27.6 & Si l-5ps; addn of Si increases
delay; 50/50( for 0.901”) 354*161; and 44.44 the heat of combstn of the mixt) 258)W. E. Schulq
/55.56( for 0.905”) 816~ 108; LA/stearic acid USP 2882819(1959) & CA 53,12681(1959) (An elec
50/50(for 0.908”) 591microsec delay] 250)W. blasting cap, less sens to static elec is formed
Maxwell et al, GerP’s 1035033 & 103613 !X1958) by surrounding the bridge wire with an ignition
& CA ~,23333(1960) [Heating masses for initiat- chge of LSt in a polyvinyl acetate binder and
ing the thermal decompn of non-detonating safety imbedding this in a static-insensitive but volt
expls. An improved (2nd patent) delay compn(3 -sensitive chge of Mg 30, Ba02 35 & Se 35%
sees) consisted of Main chge of 170g of a mixt which is ignitable by the ignition mixt) 259)R.E.
of Mg(N03)2.6H20 49.2, AN 38.8 & sawdust 12.0% Donnard,USP 2887370(1959) & CA 53, 15570(1959)
in a waxed paper sleeve, It was fed into a 680-cc [A non-corrosive primer mixt that ignites propInts
steel container with an inner diam 3 1.7mm, the consists of LSt 30-7, Pb02 5-10, Ba(NOa)2 30-5,
breaking strength of which was 1890kg/cm2. The Tetracene 3-4, PETN 0-5,Sb2S3 10-15 & Zr 5-10%]
heating app consisted of a paper sleeve which 260)D.T.Zebree,USP 2892695(1959) & CA 53,
contained an elec blasting cap and 20g chge of 17514( 1959) [Detonators with relatively low spread
Amm sulfate 35, GuN 61.5, CUCI 2.5, kaolin 0.5 in firing time are made with a delay fuse contg
& castor oil 0.5%] 251)A. Florin et al, GerP 60% of a mixt of Ba02 & Se, Te or S(75/25) and
1036735(1958) & CA 54,16833(1960) (priming 40% of an alloy of Pb & Sn(85/1 5)] 26 l)Manuf ac-
compns for fuses of improved ignitability are ture G6n<rale de Munitions, FrP 1184312(1959) &
made of LA coated with chromates, plumbates CA 54,20210(1960) (A non-corrosive primer for
or manganates SI soI in w) 252)D. T. Zebree, ammunition contains LSt 33, TI nitrate 40, CSN03
USP 2867517& 8(1959)& CA 53,5679(1959) (A 10 & Sb2Sa 17% or L.4 35, TI nitrate 35, CSN03
blasting initiator having high ignition temp, im- 20 & Sb2S3 10%) 262)G.W’.C.Taylor & S.E.
proved safety in handling & excellent firing props Napier, BritP 828148 & 9(1960) & CA 54,13666
in elec delay blasting caps consists of a mixt o f (1960) [Expl materiaIs suitable for use in delay
finely divided Pb 37-81, Te 19-65ps & an addi- or priming compns(such as LA, LA-PETN &
tive such as Mg, Al, Si, S or P. In addn to the LSt) are prepd by separating them from an aq soln
above materials 0.1-6.0% of Pb or other stearate, of the Na salt of carboxymethyl cellulose or by
palmitate or Iaurate is used to improve firing suspension in a gelatin soln contg a flash-sens
accuracy) 253)S.Kinoshita & T. Yamazaka,J apP material(such as Pb 2,4-dinirroresorcinate) which
95(1959) & CA 53,20807(1959) (A delay compn almost completely coats the expl particles]
for elec detonators, having decreased heat of 263)G.W.C. Taylor, BritP 836410(1960) & CA 54,
combustion consists of Ba02, Cr203 & a small 20209( 1960) [Prepn of expls(such as 13a styphnate
amt of org compds such as resin, rubber, oil, monohydrate, LA & DADNPh) particularly suitable
plastic & DNT) 254)H.WiHiams & W’.A.Gey, for delay or priming compns, by pptg them from an
USP 2900242(1959) & CA 53,22957(1959) (h aq medium in the presence of 2% of a colIoidal
ignition compn suitable for igniting solid pro- mixt of the Na salt of starch, amylpectin or
pellants consists of a mixt of polytrifluoro- amylose glycolate is described 264)K. Ogawa et
ethylene 50, NH4C104 50 & B 5.5-7 .5Ps) al, JapP 12093(1960) & CA 54,25829(1960) (An
255)C.A.Stokes,USP 2902351(1959) & CA 53, elec detonator in which a semiconducting SiC
22957(1959) [An igniting compn is made of a powd or a mixt of Si & Zr is placed between two
thixotropic mixt of pyrogenic Si02(50-100mm electrode s,’ above which is placed a primary powd
particle size) & 8-10% of a high-boiling aliphatic for ignition at low voltage)
hydrocarbon. This mixt is suitable for igniting
difficultly-ignitable solids] 256)D. J .Andrew Blasting Caps and Detonators, Initiating
et al, BritP 815532(1959) & CA ~,1852(1960) Efficiency of. See under Initiating Efficiency;
[A high-rate detong fuse is formed by reducing Vol l,p XVIII
the no of grains of expl(PETN,RDX,HNMnt,
LA or LSt) per linear ft of chge and by en- Blasting caps and Detonators, Tests of. see
closing the expl in a metal sheath such as VOI 1 of this Encyclopedia under Esop’s Test
 for Efficiency of Detonators, p XI; Grotta’s would be on land due to the press of the surround-
Test for Detonators,p XV, and Initiating Effi- ing water. For agricultural purposes such as
ciency of Initiating Explosives, Blasting Caps digging ditches, removing tree trunks & breaking
& Detonators,p XVII hard soil, expls of low power & brisance, such
as Black powder or low-strength Dynamites, should
Blasting Coal, Apparatus for, See Vol l,p A474-L be used(see “Agriculture and Forestry Uses of
Explosives” in Vol l,p A112-R)
Blasting Devices. See Active List of Permissible For work in gaseous coal mines the expls must
Explosives and Blasting Devices; Vol l,p A101-L be of low brisance(in order not to break the coal
into small pieces) and of low expln temp(in order
BLASTING EXPLOSIVES not to ignite the firedamp and coal dust in mines).
Explosives used in blasting operations(such as Also, the amount of carbon monoxide developed
in quarry work, non-gaseous mines, strip-coal should not exceed about 2000 liters/kg of expl.
mines, metal mines, ditching, stump blasting, Such expls are known as safety or permissible
hole drilling or in the demolition of buildings, expls
roads, bridges, railroad rracks, sunken ships, US blasting expls are manufd by DuPont Co,
under-water obstacles in channels, etc) are cal- Hercules, Atlas, Olin-hlathieson, Spencer,
led blasting explosives. Nitroglycerin Dynamites, Trojan & some other firms. Although each com-
Gelatin Dynamites, Black Powder, liquid air, pany uses its own production formulas, there
carbon dioxide & oxygen are the materials used is some info in open literature on this subject.
for commercial blasting & demolition work. For Many expls suitable for blasting(US and foreign)
military demolitions it is more convenient to use are described in Vol 1: such as Akremite(p A119-L).
TNT and plastic explosives(containing TNT, Aldorfit(A123-R), Alkalites(A127-R), Almatrites
PETN & RDX with other ingredients). The short (A 140-L), Alumatol(A 14 l-R), Aluminum-Containing
flame duration and low temp of deton re qd of Expls(A146-L to Al55-R), Amasite(A157-R),
permissible expls are not reqd in most blasting Amatex(A157-R), AmatoIs(A158-L to A165-R),
operations. Blasting expls are initiated by means American Ammonium Nitrate Dynamites(A3 55,
of blasting caps(see above) table), American Dynamite s(A167-L), Amidog2ne
The principle factors which govern the choice (A171-R), Ammoksil(A286-R) Ammons(A286-R),
of a coml blasting expl are power, brisance, den- Ammonal(A287 to A293-R), Ammoncarbonites( ~293
sity, sensitivity, stability, water-repellency & -L), Ammondynamit(A293-R), Ammonclyne(A293-R) ,
cost. These factors assume varying degrees of Ammone~A293-R to A 295-R), Ammongelatine
importance according to the circumstances under Dynamit(A295-R), Ammogelignite(A295-R), .4m-
which the expl is to be used. For blasting very monite(A 307-R to A31O-L), Ammonite-Goudronite
hard rock(such as gold quartz) a very powerful A31O-L), Ammonium Nitrate Blasting Expls(A341
and bris ant expl is required. .4s underground -L to A354-R), Ammonium Nitrate Dynamites(A355
drilling is expensive, the density of the expl -L to A356-R), Ammonium Nitrate Gelatin(A367-R
should be high. Blasting gelatin is suitable for & A368, table), Ammonpentrinit(A382-L to A382-R),
such purposes, provided it is fired with a deto- Ammon-SemigeIatin( A382-R), Amonal 1( A391-R),
nator powerful enough to produce a vel of deton Amvis Expl s(A393-R), Anchorite(A401-R), Arkite
of ca 7000m/sec(if fired with a detonator of (A480-R), Arnoudts’ Expl(A486-R.), Asphalines
only moderate power the vel of deton may be as (A496-L), AstraIit(A497-R) and Aunt Jemima Expl
low as 1500m/see). In quarrying & strip-mine (A507-R)
operations where the work is done in the open, Blasting expls starting with letters !3 to Z will
large drills are used and expl charges from 4 to be described in VOIS 2 & others
6“ in diam(and even greater) are reqd. For such The following German blasting expls(past and
work TNT, either alone or in composite expls, present) are described in PATR 2510 (Ref 8):
is very suitable but the cost is usually prohibitive Alkalsit(p Ger 3), Amatols(Ger 4 & 44), Ammonal
For under-water blasting, water-proof expls such (Ger 4), Ammoncsrbonit(Ger 5), Ammondynamit
as Gelatin Dynamites, TNT or Pentolite should (Ger 5), Ammongelatine(Ger 5), Ammonit(Ger 5,30
be used. Other expls can be used provided the & 44), Ammon-Nobelit(Ger 5), Astralit(Ger 10),
cartridges are thoroughly water-proofed. It Bikarbit(Ger 11), Calcinit(Ger 27), Carbonit(Ger
shou!d be noted that the effect produced by an 25), Cheddit(Ger 27), Chloratit(Ger 28), Chrom
expln under water is considerably less than it -Ammonit(Ger 28), Commercial Expls(Ger 29),

—.
 B 203

Dahmenit(Ger 32), Demolition Expls(Ger 34), cal blocks 7cm lcng & 3cm diarn, weighing 75g.
Detonit(Ger 35), Ilonarit(Ger 30 & 38), Dualin(Ger They were used during WWII(Ref 3a)
38), Dynamit(Ger 30 & 39), Ersatzsprengstoffe Re/s: l)Marshall 2(1917),p 569 2)Meyer(1943),
(Ger 43), Fordit(Ger 52), Formit(Ger 52), Fulmenit pp 392-400 3)Anon, “Explosives and Demolitions”
(Ger 53), GeIatine-Astralit, -Carbonit, -ChecIdite IJSDept of Army Field hianual FM5-25(1945)
& -Dahmenit(Ger 66); Gelatine-~onatit( Ger 30 & 3a)Blinov 1( 1948),17 4)OlinIndsInc,Explosives
66) Gelatine-Dynamit, -Leonit & -Prosperit(Ger Products Bull, 2nd ( 19~0) 5)Kirk & Othrner 6
67); Gelatine-Rornperit & -Tremonit(Ger 68); (1951),pp 60-74 6)Blasters’-Hdb( l952) 7)~~.de
Gelatine-Tetter-Astralit & -Nobelit(Ger 68} C. Crater et al, IEC 50,N0 7,40A(1958) 8)PAT?l
Gelatit & Ge silit(Ger 68); Gesteins-.Albit, -Dorfit, 2510(PB Rept 161270) (1958)
-Koronit, -Permonit,-Persalit & -westfalit(Ger 69);
Haloklastit(Ger 87), Hexa Expls(Ger 44 & 88), Additional References on Blasting Explosives
Kessen Expls(Ger 101), Kinetit(Ger 101), Kh!A l)H.D.Farris & A. C.Jex, USP 891334(1908)& CA
13xpl(Ger 44); Kohlen-Carbonit, -Koronit & -Salit 2,2995(1908) [KC103 661b, wheat flour 331b, PA
(Ger 101); Kohlen-Westf alit(Ger 102), Kolax(Ger loz(all blended and coated with 1 gal coal oil),
102), Koronit(Ger 102), Neurodit(Ger 116), I-IN03 1.502 & HCI 10Z]
Neudahmenit(Ger 117), Neunobelit(Ger 117), 2)W.Eberle,FrP 392378( 1908) USP 910365( 1909);
Neuwestfalit(Ger 117), Nitrobaronit(Ger 118), CA 3,1088(1909)& CA 4,2733(1910 (KN03 12,
Nitrolit, Nobel it & Nobel’s Wetterdynamit(Ger 122); S 3, charcoal 1 & pulverized horse dung lp)
P erchloratit(Ger 128-9), Perch lorit(Ger 129), Per- 3)C.Pieper, BritP 15916(1908)&CA 4,112(1910)
coronit & Perkoronit(Ger 12>30); Perdit & P ermonit (NH4C104 42, NaN03 31, TNT 14 & paraffin wax
(Ger 129); ,Persalit& Petroklasist(Ger 130> Roburit 13%)
(Ger 160), Romperit(Ger 169), S-16LZ S-19 Expls(Ger 4)H.D.Farris & A. C.Jex, BritP 20574( 1908) & CA
44); Sekurit & Sekurophor(Ger 174); Stonit(Ger 191), 3,1929(1909) [KCIO 53, KNOa 5, Ca(OH)2 6,
Tetansprengstoffe( Ger 196), Thunderit(Ger 198), wheat flour 33, PA & KC103 2 and lamp bIack 1%]
Totalit(Ger 199), Tremonit(Ger 203), Unter- 5)(?)KIaffke, FrP 396496(1908)&CA 4,2733(1910)
wassersprengstoffe( Ger 212), Westfalit(Ger 226) (KN03 73.9, carbon 13.4 & cellulose 12.7%)
and Wettersprengstoffe( Ger 226 & 262 and tables 6)H.F.Easton, BritP 18551(1909)& CA 5,198(1911)
on pp Ger 260-1. Tk se include Wetter-Age sid, [Ba(N03 )2 80, TNT & Al powd 20%]
-Albit, -Ammoncahtisit, -Arit, -AstraIit, -Baldurit, 7)G.M.Peters & M. F. Lindsley, USP 953798(1910)
-Barbarit, -Bavarit, -Carbonit, -Dahmenit, Qetonit, & CA 4,1678(1910) (AN 75, nitrated wood fiber 20,
-Donarit, -Dynamit, -Dynammom, -F ordit, nitrobenz 4 & asphalt 1%)
-Fulmenit, -Lignosit, -Markanit, -Monakit, 8)C.Arnoudts, USP 964365 (191O) & CA 4,2733(1910)
-Nobelit, -Perchlorit, -Persalit, -Salit, -Siegrit, (KC103 60, sugar 40, turpentine 2, vegetable tar
-Sonnit, -Wasagit, -Westfalit & -Zellit) 2 & KMn04 0.00125ps)
For military demolition purposes, the foIlowing 9)J.E.Bronstein, USP 986900(1911)& CA 5,1995
explosives have been used: (1911) [AN 82.2, sugar 9 & Fe pyrites(FeS2) 8.8%]
USA: TNT(demolition blocks), NS,RDX Composi- 10)G.hLPeters & M. F. LindsIey, USP 994273(1911)
tions C, C-2 & C-3(plastic), Tetrytol, Pentolite, & CA 5,2557(1911) [AN 67, NaCl 20, nitrated wood
AN (catering), Dynamites & Blasting Gel atin(Ref fiber 10, asphalt (20% soln in nitrobenz) 2 & CaC03
3,p 3) 1%1
GtBrit TNT, TNT/Tetryl-70/30, Expl 808(De- ll)G.M.Peters, USP 1048578(1913) & CA 7,703
sensitized Polar Blasting Gelatin), TNT/PETN (1913) [AN 75, nitrated potato meal 20 & asphalt
-50/50 or 75/25, Ammonal and Gelignite(Ref 3, (20% soln in MNB) 5%]
pp 126-127) 12)A.B.Cole, USP 1126401(1915)& CA 9,717(1915)
Germany: TNT, PA, TNT/PETN/wax, PIastite (KC103 30, sugar 25, coal or coke powd 22, NaN~
(RDX/OIL), RDX/PETN & PETN/wax(Ref 3, 129 20, MeOH 2, Khln04 0.5 & lampblack 0.5%)
-131) 13)C.Schanandoah, USP 1141009(1915)& CA 9,
France: hielinite(Picric Acid) (Ref 3 ,p 135) 1845( 1915)[Alum 1 & sugar 16ps (moistened with
Italy: TNT, PETN(Ref 3,p 136) coffee extract and boiled with MeOH until dry)
Japan: PA(compressed or cast), RDX/vegetable mixed with 1 1/2 times its wt of KC103 just
oil-80/20(plastic) (Ref 3,pp 133-134) prior to use]
Russia: TNT in rectangular blocks 5x5x10cm & 14)K.Arklow & L.H. Pirmez, BritP 110237(1916)
5x2. 5x10cm, weighing 400g & 200g or in cylindri- & CA 12,428(1918) (AN 65, NG 11, wood meal 5
 1

B 204

&CaF2 19%) (1925) (Ho11ow solid cylinder of cast TNT, PA or

15)J.L.Dormer, USP 1214765(1917) & CA I 1,1042 mixt TNT/PA fiIIed with a powd mixt of AN &
(191 7) [Sugar 45-48 & H20 l-2(melted) and suc- nitrated hydrocarbons)
cessively added: Mn02 1-2, crude petroleum 1-2 & 28)R.L.Hill,USP 1483087(1924) & CA 18,1053(1924)
KCIO~ 46-49% and the mixt granulated and dried] [AN 17.5-52.5, NG or Tetranitrodigly cerin 3-3.5,
16)0. B. CarIson & E. F. Otterdahl, USP 1277043 NaN03 24-52,5, CaC03 0.5, nitroaromatic compds
(1918) & CA ]2,2127(1918) [NH4C104 70-85, Fe-Si (at least 50% TNT) 20-4 & S O-2ps]
5-15, wood meal 1-10, mineral oil(fraction bp 29)J.Marshall, USP 1509362(1924) & CA 18,3722
above 250° and rich in naphthenes) 2-15 & NC(gek ( 1924) [Ground smokeless proplnt (gelatinized
atinized with ‘fliq TNT”) 5-20ps; NaN03 is added with 1-10% DNT) 25% with NaN03, CaC03 or Al
if the expl is used in mines] added]
17)W.Rintoul & T. J. Nolan, BritP 131389(1918), 30)L.0.Bryan,USP 1509393(1924) & CA 18,3722
USI’ 1348741( 1920) & CanP 217254(1922); CA 14, ( 1924) [AN, ground smokeless proplnt, NG, NaCl,
350,2989(1920) & 16,1868(1922) [NC(12.2%N) 50, NaN03 & CaCOa]
NG 41, benzyl-p-tolylurethan 8.5 or phenylbenzyl- 3 l)W.M.Dehn, USP 1509935(1924) & CA 18,3722
urethan 8 & ethyl-~ -naphthyl ether 0.5 or diphenyl- (1924) (NaN03 1-4, sawdust 1.5-6.o & AN 3-7Ps)
urethan 1%1 32)F.Olsen, USP 1510555(1924) & CA 18,3722
18)L.O.Bryan & W. R. Swint, USP 1327859(1920) & (1924) [NH4C104 o-40, TNT 0.50, smokeless
CA 14,843(1920) (NaN03 43-57, TNT 18-51, NG 5, proplnt 15-50, combustible non-expl material(such
wood puIp O-5, cornmeal O-8, S O-7 & CaC03 1%) as woodmeal or “vegetable ivory”) 3-10, paraffin
19)R. L. Hill, USP 1334303 & USP 1360397-9(1921); 0-30, KN03 0.30 & hln02 O-30ps]
CA ]4,1609(1920) & 15,599(1921) (N~C104 45-55, 33)C.D.Pratt, USP 1563924-6(1925) & CanP
NS 35-45 & NaN03 10%; a small amtof oil, a liq 259355-6(1926); CA 20,505 & 2415(1926) [The con-
nitrocompd, Mn02 & S may also be added) stituents of BkPdr(NaNO~ 45-65, S 1-15 & charcoal
20)J.R.Mardick, USP 1335788 l_JSP ~335790(1920) 10-2 5%) mixed with carbohydrates (starch and/or
[TNT(or PA) 20, Fe-Si(82%) 12, AN 40, NaN03 paraffin) 1-35 & a metallic or NH4 chloride, oxa-
21.5, DNT 3, woodflour 3 & CaC03 0.5%; TNT(or late or tartrate 1-15% to reduce tendency to ignite
PA) 25, Fe-Si(82%) 7, KC104 50, NaN.03 12.5, flammable gases & dusts]
woodflour 5 & CaCOa 0.5%; TNT(or PA) 20, Fe-Si 34)N.A.Unger, USP 1566784(1925) & CA 20,505
(82%) 12, NH4C104 35, NaN03 26.5, DNT 3, WOO& ( 1926) [AN 50-85, Si 10-40 & NG(gelatinized
flour 3 & CaCOa 0.5%; or AN (coated with 3% with NC) l-15ps]
gelatinized DNT) 40, TNT 15, DNT 32 & Fe-Si 35)C.D.Pratt, USP 1590393(1926)& CA 20,3086
10%1 (1926 )[The constituents of BkPdr mixed with a carbo-
21) A. Langmeier, USP 1367608(1921) & CA 15, hydrate(cellulose, glucose or starch) & with NH4CI
1077(1921) [NaN03,(coated with TNT) 49, in order to lessen their tendency to ignite flare -
NH4C104(coated with TNT) 20, TNT 20, S 10 mable gases] (Compare with Ref 33)
& woodpulp 1%] 36)R.A.Long, USP 1698674(1929)& CA 23,280
22)P.N.Stankovitch, USP 1412319(1922) & CanP ( 1929) [NG (up to 8%) + TNT(together not in
229108(1923); CA 16,2226(1922) & 17,2051(19231 excess of 12%) & ground wood]
[NaNOg, flour middlings(med size particles 37)L.N.Bent, USP 1706517(1929)& CA23,2297
separated in sifting ground grain) & S impregnated [NH4B03, NaN03, NG & ground wood(pine or
with a 10-20% soln of DNT in NG] spruce)]
23)L.0. Bryan, USP 1420364(1922) CA 16,2992 38)E.Sorenson, USP 1709498(1929)& CA 23,
(1922) (NC 40-65, NaNO~ 30-50, Al pdr 0.3-5, 2827( 1929) (AN 800, KN03 100, S 16, Mnoz 15,
NG 1-10 & CaC03 1%) paraffin 6, petr naphtha 6, rosin 15, potato flour
24)E.M.Wemer, USP 1430272(1922) & CA 16,4067 8, Al 30 & NG loops)
(1922) [NaC103 70.5, sugar 18.75, AI powd 3 & 39)J.P.Nienhuis, BritP 297365(1927)& CA 23,
resin(20% soln in nitrobenz) 7.75%] 2827(1929) (Oil or asphalt pitch, with or w/o char-
25)E.I.duPont, BritP 184487(1922) & CA 17,211 coal, KN03 & S)
( 1923) [Ground smokeless proplnt(mainly NC), 40)C.H.’~]aters, USP 1786046( 1930) & CA 25,595
Cordite, NaN03, chalk & H20] (1931) [NaC103 1, Iiq hlNT 3 & liq DNT llps
26)A. J. Strane,USP 145530~1923) & CA 17,2365 (NaN03, CaC03 & sawdust maybe added) for
( 1923) (hlixt of colloided NC powd & BkPdr) stump or rock blasting]
27)L.Yonck, BritP 216061(1923)& CA 18,3479 41)P.Naoiim, GerP 513654(1930) & CA 25,4710

——. ,. .. .— —...————-_.—
 B 205

( 1931) [Ca(N03 )Z(dehyd above 100°) 62-70%, TNT, (1935) (AN 5-30, NaN~a 4040-75. charcoal 1-20, S 1-20
charcoal & NG] & woodpulp 1-10%, shaped in the form of a block, d 0.9
42)R.L.Hill, USP 1833573(1931), USP 1845663-4 -1.30) 56)L.E.Clapham, CanP 350872(1935)& CA~
(1932 ),USP 1850106 (1932 )& FrP 716532(1931} 5658(1935) [Mixt of NG & NGc 14.0, AN 44.5,
CA26,1125,2320 &2867( 1932) [NH4C10a or AN NsN03 13.0, NaCl 11.0, peat(5Z1120) 17.0,
(coated with graphite, rosin, paraffin, sand, char- resin 0.25 & (NH4)2HP04 0.25%]
coal, TNT, NC or carbohydrate) mixed with grains 57)N.G.Johnson & H. A. Lewis, CanP 350873
‘of BkPdr] (1935), USP 2033 196(1936); CA 29,5659(1935)
43)A.S.O’Neil & A. G.Schuricht, USP 1849378(1932) & 30,3240(1936) (Three compns: PETN 35.0,
& CA 26,2867(1932) (NC 88-99 & TeNA 1-12%; NsN03 56.0, S 5.0, chalk 3.5 & engine oil 0.5%;
other nitrocompds may be added) _PETN 12.0, AN 66.5, NaN03 10.0, carbonaceous
44)W’.C.Holmes, USP 1905289(1933) & USP 1927832 material 9.0, Iiq DNT 2.0 & chalk 0.5%; or PETN
(1933); CA 2~,3612 & 5981(1933) (NG, MgO & 16.0, AN 50.0, NaN03 21.0, carbonaceous mate-
Nitrosugar or NG & ca 0.4% triphenyl phosphate, rial 9.5, NG 3.0 & chaIk 0.5%)
with other ingredients) 58)D.D.kliceIi, FrP 783835(1935)& CA 29,8335
45)Lignosa Sp61ka Akcyina, BritP 388508(1933)& (1935) [KC103 60, “latoz” (?) 20 & boiled potatoes
CA 27,5981(1933) (AN 66, NsN03 12, NaCl 10, 20%1
woodmeal 10 & charcoal 2%, with 2.75-6.35 qts 59)N.G.Johnson & C. A. Woodbury, CanP 352763
H20 per 220 cu in of nitrates &‘ woodmeal) (1935) & CA 29, 8335(1935) (NG 47.0, DNT 3.0,
46)A.C.Scott, BritP 397203(1933)& CA 28,900 NC 1.3, NsNO~ 36.1, cereal 9.0, starch 2.7 &
(1934) [AN with NH4C1, NaCl, (NH4)2CZ04, chalk 0.9%; NG 60.0, DNT 3.5, NC 2.3, NaN03
NsHC03 , ZnS04 , MgS04 or Na$04 added & 2.2, AN 24.0, cereal 6.0, starch 1.0, & chalk 1.0%;
asbestos 1-2%; dec by heat and yields non-flam- NG 30.0, DNT 2.0, NC 0.7, NsN03 44.8, NH4C1
mable products- when ignited with B kpdr or 15.0, ctreal 2.0, starch 4.5 & chalk 1,0%; and
KC103 & cellulose acetate] NG 22,0, DNT 1.5, NC 0.2, NaN03 9.0, AN 60.0,
47)Akt-Ges Lignose, GerP 579815(1933)& CA cereal prod 6.9, & chalk 0.4%)
28, 1193( 1934) (Addn prod of PbO & neutral Pb 60)A,Lance, BritP 432308(1935)& CA 30,617-8
picrate as principal c onstiruent of blasting chges) (1936) [Liq O with absorbent ceIlulosic material
48)w.de C. Crater, USP 1945344(1934)& CA~8, (sawdust, cork or peat) mixed with high-bp hydro-
2538(1934) (AN, NsN03 & tryst nitrolactose; carbons (petr jelly or vaseline) up to 2070 & other
woodpulp, TNT, or DNT may be added) ingredients, such as MgC03 or kieselguhr 10-15%
49)W.E.Kirst & J. Marshall, CanP 339433(1934)& (to reduce its strength) or AI or Fe-Si(to increase
CA 28,2908(1934) (AN 58, NG 15, NaN03 9 & its strength)]
cornstaIk pitch 18%) 61)SOC Anon d’Arendonck, BritP 432850(1935) &
50)C.A.Woodbury, Canp 339468-9(1934) & USP CA 30,617(1936) [A compn used to prevent ig-
1965731(1934); CA 28,2908 & 5672(1934) [NG nition of flammable gases in blasting contains
86-92, kieselguhr 3-6% & NC; NC 1-5 & dope potash feldspar with other ingredients. One ex-
material 3-10ps (gelatinized with 33-92Ps Iiq ample: orthoclase(KAlS130a) 55, K2S04 35 &
nitric ester); NG 90, NC 5, woodpulp or bagasse plaster of Paris or clay 10%. This compn is
pitch 5%] preferably made into a sheath surrounding the
51)H.A.Lewis, CanP 340%6(1934) & CA 28,4234 blasting expl but up to 30% may be incorporated
(1934) (AN 75, 0 or 52; NG 10, 60 or 23; NsN03 in the expl itself composed of NG 11, DNT 1,
5, 20 or 14; treated sunflower stalks 8, 5 or 2; NaCl 22, AN 59, cellulose 6.85 & lamp black
& other combustibles 2, 15 or 19%) 0.15%1
52)A.G.White & ICI, BritP 412583(1934)& CA 29, 62)H.T.Simpson, 3ritP 435588(1935) & CA 30,
346, 1935) (Mixt of NG & NGc 15, AN 8.5, NaN09 1564( 1936) [A mining & quarrying expl: AN 90,
12.0, plant fiber 6, NaCI 58 & N~H2P04 0.5%) Al(coated with paraffin) 6.5 & Mn02 3.5%]
53)C.Wache, BritP 415806(1934) & CA 29, 1251 63) E. I.duPont, BritP 437035(1935)& CA 30,3239
(1935) (Mixt of a metallic nitrate & sl nitrated (Non-gelatinous blasting expl: AN 58, NaNOB
cellulose) 20.2, PETN 15, TNT 6, hydrocarbon oil 0.3 &
54)J.A.Wyler,USP 1985968(1935) & CA 29,1252 chalk O. 5%)
(1935) (TeMNe & hlNX with AN, NaNO~ NS, NC, 64)ICIANZ, AustraIianP 25791/35 (1936)& CA 31,
TNT, Al, ZnO & cornmeal) 3698(1937) (BkPdr chge in juxtaposition to an
55)W.E.Kirst, CanP 350400(1935) & CA 29,5274 exothermic chge of lower rate of combustion con-
 B 206

sisting of charcoal or woodrne al & AN, alkali 100 & NC(12%N in 40% acet soln) 40ps or urea
metal or Amm perchlorate; fineIy divided metals nitrate 100, NC(12%N) 20 & NC (13%N) 10ps]
or metal-silicon aIloys must be absent) 78)L.S.Byers, USP 2136205(1939) & CA 33,1500
65)R.C.Payn & A. G. White, CanP 362019(1936) (1939) (Blasting powder pellets formed of a
&CA 31, 1617( 1937) [Cooling sheath for blasting core of NaN03 coated with NG and an outer layer
expls: NaHC03 100, gelatin soln(lO%) 50 & of nitrate, perchlorate & Al)
glycerol 10ps is formed into a sheet and dried to 79)H.G.Pert, USP 2167849(1939)& CA 33,8993
a moisture content of 3%1 [A mixt of sucrose 24 & KNO~ 33(both dissolved
66)J .Taylor, CanP 362020(1936) & CA 3 ],1616 in hot w) with finely powd coal 10 & KC103 33%
( 1937) (Blasting expl for use in fiery mines: AN is grained and dried]
60, NH4C1 69 & soda ash 2ps by wt of total mix) 80)H.H.Holmes, USP 2168030(1939) & CanP
67)A.G.White, CanP 362021( 1936) & CA 31,1617 384570(1939); CA 33,9648(1939) & CA 34,1488
(1937) (Core expl: NG 10, AN <66.5. NaCI <15.0 ( 1940) (AN 15-45, Al 1% and the remainder BkPdr)
& woodmeal 8.5% sheathed with a solid cooling 81)M.H.Wahl, USP 2171379(1940) & CA 34, 265
material, NaHC03 & NaF, not exceeding 30% of (1940) [Coal mining expl: AN, binding agent &
the wt of the expl core; or Ca silicide 1 & AN ground smokeless proplnt (5@mesh)]
4ps) 82)C.0.Davis, USP 2185248(1940) & CA 34,3092
68)A.G.White & E. Jones, USP 2075969(1937) & (1940) [AN 92, DNT or MNN 4 & DPhA or p-tolu-
CA 3 1,3698( 1937) (Safety cartridge or bore hole idine 4%]
chge: core of Bkpdr & a sheath of Na or Mn 83)M.A.Cook et al, USP 2199217-8(1940)& CA 34,
borate) 6078( 1940) [Coal mining expl: AN (agglomerated
69)F.E.MiIler & J. D.hlcLeod, USP 2078264(1937) by starch) coated with 10% NG]
& CA 3 i ,4500( 1937) (Nitrated naphthalene mixed 84)R.W.Cairns, USP 2211738(1940) & CA 35,625
with PA, NsN03 & other ingredients) (1941) [AN (coated with rosin or dammar & paraffin),
70)L.S. Byers, USP 2079105(1937) & CA 31,4500 NG & woodpulp]
( 1937) [A!kali chlorate & alkali nitrate mixed 85)A.H.Garcia, USP 221 5608( 1940) & CA 35,898
together with liq DNT isomers(mp 3-15° ) & ground ( 1941) [Quarry & mine expl: KC104 65, Mn02 1.3,
wood(20-60 mesh)] NsNO~ 5, (CH2)6N4 1.4, S 1.3, sucrose 26 & Fe
71)M. F. Lindsley, Jr, USP 2079558(1937) & CA 31, filings lpl
45oo( 1937) [AN, NsN03, KN03 or Ba(N03)2, tar 86)M.A.Cook et al, USP’S 2220891-2(1940) & CA
char & S; paraffin and a coating of NC or NG 35, 1636(1941) (Blasting expl having d over 1.15
may be used] are formed by combining AN >50% with other in-
72)P.Parodi-Delfino, USP 2079792(1937) & CA gredients)
31,5165(1937) (Tetraacetate of pentaerythrite 87)H.G.Pert, BritP 531082(1940)& CA 35,8299
with TNT or NC & NG) (1941) (KC103 33, KN03 33, sucrose 24 & finely
73)D.C.McMeans, USP 2109049(1938) & CA 32. powd coal 10%)
3156( 1938) (Underground blasting expl: Kc] Oq 88)C.S.Hallet, BritP 5308 18(1940) & USP 2263406
35, sugar 35, woodpulp or sawdust 10, DN”~- 12, ( 1941) & CA 36,272 & 1496(1942) [Coal mining
toluene 6 & petrolatum 2%) expl: KC104, coal-tar pitch, sugar, a bichromate
74)M. A. Nice, USP 2120503(1938)& CA 32,6064 (not over 6%) & an alkali metal chloride(ca 26%)
(1938) (Nongelatinous blasting exPl: NG 22-28, 89)C.H.Winning, USP 2231043( 1941) & CA 35,
AN 26-46%, with NC & woodpulp of flour added) 3445( 1941) (NG & AN, coated with starch,
75)A.Ignatieff & Heaters Ltd, BritP 480330(1938) gelatinized in w by thiocyanate, urea or dicyano-
& CA 32,6463(1938) [Combustible gas-producing diamide)
chge: KC104 60, salicylic acid 9, castor oil 1 & 90)V.H.WiIliams, USP 223’5060(1941) & BritP
(COONH2)2 30%; KC104, starch, borax, castor 522989(1940); CA 35,4210 & 61 14(1941) (AN
oil & (C00NH4 )2; or KC103, charcoal, MgS04 & coated with baIsa woodmeal in the presence of
castor oil] w & granulated)
76)A.G.White, USP 2128576(1938) & CA 32,8782 91)J.W.Dawson & W.M. Dehn, USP 2255653( 1942)
( 1938) (Composite blasting calu,age or borehole & CA 36,272( 1942) [AN, woodmeal, S, NG & hexa-
chge: 13kpdr in juxtaposition to a slow-burning chloronaphthalene( 4-5%)]
expl mixt, charcoa 1 & AN fCom~are with Ref 64) 92)M.A,Cook, Canp 411896( 1943) & USP 2312752
77)J. Taylor et sI, BritP 488584(1938) & CA 33, (1943) & CA 37,3943 & 4902(1943) [ExPI blasting
386( 1939) [Gas-producing safe blasting chge: GuN unit for oil-well shooting: AN (at least 50%),
 B 207

PETN or Tetryl or TNT& Ca(N03)2 + NH3] free from NG; and a detong expl: ~, combustible
93)C.H.Winning, USP’S 2314806-10(1943)& CA carbonaceous material(such as S, woodpdp, veg-
37,5241(1943) [Various blasting expls: AN, AI etable merd, rye flour or flaked cornmeal) & NG
or NG & barley meal; AN, NG(not more than 25%), absorbed in the blended granules]
Al & rye flour; AN, NG or Al & spelt meal; AN, 105)C.D.Bitting, USP 2395367(1946)& CA 40,
Na Nitrate, -chlorate or -perchlorate, NG or Al & 36W( 1946) [permissive expl for coal mines:
oat flour; or AN, NG or Al & cereal meal(species ?elleted mixt of AN, binding agent & NG( 5-15%)]
Andropogon sorghum)] 106)J.Barab, USP 2398071(1946)& CA 40,4218
94)R.W.Lawrence, USP 2325064-5(1944)& USP ( 1946) (AN, DNT or mineral oil & coal or carbon-
2338120( 1944); CA 38,256 & 3478( 1944) [Open black)
-pit mining or quarry-blasting expls such as: 107)C.H.Winning, CanP 435456(1946) & CA 40,
mixt of AN, nitromethane & woodmeal or balsa 6818(1946) (AN, with NG 3-25 & barley meal not
(or bagasse); mixt of HN03 & nitromethane or over 0.15%)
other nitrated hydrocarbons; or AN, carbonaceous 108)C.S.Hallet, BritP 575147(1946) & CA 41,4312
material, NG & one or several nitrated hydro- ( 1947)( Expl less susceptible to extreme temp than
carbons] dynamite: NG & a small amt of NH4 trinitrocresylate)
95)R.W.Cairns, USP 2338164(1944)& USP 2355269 109)C.D.Bitting & R. W. Lawrence, USP 2433417
(1944); CA 38,3478& 6564(1944) [AN, KNO~ or (1947) & CA 42,7045(1948) (An expl consisting of
NsN03, pine-wood resin(petroleum insol) & NG] NG, NC, NaN03 & woodpulp is improved in its
96)W.deC.Crater, USP 2340304(1944)& CA 38, ability to fire under high liq press or after long
4134( 1944) (Inositol Hexanitrate, NG, carbonaceous immersion in w, by incorporating ca 3% cornmeal
material & oxidg agent) impregnated with 25% of a heat-hardenable urea
97)S.B.Watt & N. W. Adolph, USP 2344840(1944)& -CH20 or phenolic resin)
CA 38,3842(1944) [AN, 60-89, NG(contg 0.05% NC) 110)E. Whitworth et aI, BritP 591755( 1947) & CA
3-5, NsN03 2-20 & Al powd 1-2%1 45,862( 195 1) [Low-density blasting expl: solid
98)J.Whetstone & ICI, BritP 552645-6( 1944) & salts, NG & NC(stabilized, with N content below
CA 38,4134( 1944) [TNT(emulsified), AN & 12.3% & not swellable by NG)]
Ca(N~)2.4H20 or N~03] 1 ll)R.J.W.Reynolds et al, BritP 593 163(1947) &
99)D.G.Morrow, USP 2355817(1944)& CA 39,194 CA 42,9180(1948) [Sens to deton of bIasting
(1945) (Quarry, open-pit metal mining & mihuy gelatin on storage is prolonged by incorporating g
blasting expl; liq N204 & CH3N02, C2H~N02, 0.05-0. 50% of a so-called ‘NC cross linking agent’
C3H7N02 or C4H9N02 proportioned to give an O such as hexakis(methoxymethy l)-melamine, bis(bu-
balance betw -25 & +25%) toxymethyl)-urea, kxamethylene diisocyanate or
100)C.O.Davis, USP 2356149(1944) & CA 39,194 N, N’-bis(hydroxymethy l)-adipamid e]
(1945) (AN or NH4C104, woodpulp & S or Al & l12)E.Whitworth & J. C. HornelI, BritP 595443
TNT prepd in block form) (1947) & CA 48,6699( 1954) [Low d blasting expl
10l)C.O.Davis et al, USP 2362617( 1944)& CA suitable for use in gassy or dusty mines: 80/20
39,2880( 1945) [Deton vel of blasting gelatin is -NG/NGc 6-12, peat 7%, NGu 10, AN(O.8 bulk d)
greatly enhanced by incorporating one of the 57-59, resin 0.5, (NH4)2HP04 0.5 & NaCl 11-17%.
following compds(preferably 100 mesh): 0.4-2%?@ This expl of bulk d 0.73-o.76 is particularly use-
Cu, Ti, Pb, Sn, Al or Fe(trivalent) oxide or 0.05-5% fuI in obtaining lump coal]
of the hydroxide or normal or basic salt of Pb, Fe l13)J.Whetstone & J. Taylor, BritP 597716&8(1948)
or Al] & USP 2548693(1951); CA 42,4349(1948)& 45,
102)L.N.Bent, USP 2362878(1944) & CA 39,2880 10590( 1951) [AN 50, urea 25, Na acetate trihydrate
( 1945) [Liq nitric ester(NG),catbonaceous materi- 15 & Na2S203. 5H20 IOps are mixed and heated to
al & Ca(N03)2] form a Ii% 80ps of this Iiq are mixed with 20ps
103)C.D.Bitting & R. W. Lawrence, USP 2365170 NG(contg 1% NC) to form a gelatinous expl. An-
(1944) & CA 39,3936(1945) [Cellular carbonaceous other mixt contains: AN 34 & Ca(N03)2.4H20
material(such as cork, balsa, bagasse, etc), hard- 66ps geHed by addg cornstarch 16ps & heating
ened in situ with a synth thermosetting resin & to 900 for Xhr]
s atd with NG] 114)H.R. Wright & W.G. Al Ian, USP 2439328(1948)
104)E.I.duPont & C. O. Davis, BritP 5646027(1944) & CA 42,4350(1948) (Plastic expl: PETN or
& CA 40,3606( 1946) [Coal blasting expl: AN & HNMnt & RDX distributed in a mixt of dinitro-
oxidg material imbedded in a matrix of AN, compn cumene, dinitro-tert-but ylbenzene & the di-
 I

B 208

nitration prod of sec-butylbenzene) under hydrostatic press of 40atm: NG & EGDN

115)”Montecatini”SGIMC, ItalP 433633( 1948) & CA (80/20) 57.5, NC 2.4, woodmeal 10, NsN03 24-8,
44, 1709( 1950) (RDX 75 & Nitroisobutylgly cerol tr; finely milled barytes 5 & chalk 0.3%; for seismic
acetate 25%, melted at 80°) prospecting & for well blasting: NG & EGDN
116)PGS, ItalP 433636( 1948) & CA 44,1709(1950) 80/20) 57.5, NC 2.5, deproteinized, de-oiled
[TNT 30-90, RDX 5-65 & powd metal(Si,B,Mg,Cu, peanut meal( 16/100 BSS screen) 13, NsN03 26.4,
Fe,Al or Zn) 5-30ps] chalk 0.3 & (NH4 )zHP04 0.3%]
117)E.Whitworth & J. C. Hornel, USP 2470733( 1949) 128)C.D.Goodale, USP 2615800( 1952) & CA 47,
& CA 43,5594( 1949) (Blasting expls are stabilized 2487( 1953) (AN expls are made less hygro & less
by addn of approx 1% of a neutral mixt of alk w-sol by coating them with O. 1-5% of 2,2-Dinitro-
metal dihydrogen orthophosphate & dialkali metal propane combined with 5-30% of a non-volatile
hydrogen orthophosphate) liq; the sens & performance of the expl is main-
118)J .Taylor & O. A. Gurton, USP 2481795( 1949) & tained during storage)
CA 44,840(1950) {Blasting expl for gassy or dusty 129)J .Taylor, BritP 682209( 1952) & CA ~, 11672
mines: AN 48.6, NH4C1 21.3, limestone fines (1956) (Low-density safety blasting compn:
20.1 & expl jelly [99%NG/EGDN(80/20) & 1% NC 80/20 NG/NGc 10, peat 12,AN 55.5, NfiOS 10!
(11.95-12 .25%N)] 10%] dendritic NaCI 12, (NH4)2HP03 0.2 & rosin 0.3%.
119)PGS, ItalP 445206 & ItaIP 445601-3(1949); This compn has a packing d of 0.62, a rate of
CA 45,1770 & 3160( 1951) (TNT 30-90, PETN 5-65 deton of 1450 m/see and a power 59% that of
& Al 5-30%; TNT 15-45, DNN 15-45, PETN 5-65 & blasting gelatin)
AI 5-30%; or TNT 15-45, DNN 15-45, RDX 5-65 & 130)K.Hino & J.Sate, JapP 6196(1953) & CA
Al 5-30%) 48, 117’90(1954) [Colloidal =@ NG 9, Nc 1,
120)G. A. Lyte, USP 2499321(1950) & CA 44,468o AN 52.5, urea 8, CO(NHZ)2.HN03 24.2& HN:C-
( 1950) (An expl relatively insens to impact & (NH2)2.HN03 5.3%]
friction but initiated by a No 1 detonator: AN 131)J.Sante, JapP 296(1954) & CA 48, 13222( 1954)
50-68, PETN 3-10, TNT 4-15, NsN03 7.5-25, (NHZCONHN02 35-60, AN 20-40, NG 3-20
mineral oil 0.4-0.7 & Al pdr 2-2.5%) & urea 1-5%)
121)S.H.Davidson et al, BritP 645039( 1950) & CA 132) A. Sato,JapP 988(1954) & CA 48, 14210(1954)
45,4043( 195 1) (AN blasting expl is improved in (NG O-10, AN 60-45, RDX 15-20 & hydrated potter’s
resistance to w damage by incorporating in the clay 25%)
mixt a water-soI methylcellulose) 133)T.Sakurai,JapP 989( 1954) & CA 48, 14210(1954)
122)J .Taylor, USP 2548688(1951)& CA 45,10590 (NG 0-10, NC O-G5, AN 35-60, carbohydrate 0.5-5,
(195 1) [NC(moistened with an alc soln of eutectic w 5-15, NaCl and seaweed 5-25 & woodpowd &
AN & urea) & NG to give a non-tacky soln, w/o starch O-10%)
the desensitizing effect of water-dampened NC] 134)N.Sakurai, JapP 990(1954) & CA 4$14210
123)H.H.F assmacht & C.A. Woodbury, USP 2548880 (1954) [Water(8%) is added to a mixt of Na cel-
(1951) (Gelatinous expl: DNT 10, TNT 4, MNT 5, lulose glycolate 0.8, glutenous rice powd 2.5,
RDX 77, NC 1 & Tetryl 3%. Prod has d 1.58 and glutenous millet powd 2.5, nonglutenous rice powd
vel of deton 7000-8000 m/see and is substantially 3.0, flour 3.5 & potato starch 4. 5ps. This compn
less sens to shock than std gelatin dynamite) (8.8-12.5%) is added to 87.5-91.2% of a mixt of
(Note: This mixt is same as RDX Comp C-3) NG 22, NC 1, AN 66.2 & woodmeal 2ps]
124)S.Fordham, USP 2554179(1951)& CA 45,7345 135)H.R.Wright et al, BritP 713758(1954) & CA
(1951) [Blasting gelatin: NG 91.4, NC(contg 2% 49,3537( 1955) [Improved gelatin blasting expl:
sulfonated methyl ole ate) 8 & CaC03 0.6%] p-tert-octylphenyl diethyl phosphate 0.20 &
125)S.Fordham, USP 2554180( 1951) & CA 45, O-CH3C6H4N02 3ps are dissolved in 21ps of a
9863( 195 1) [Blasting gelatin: NG & NC(contg nitrated 80/20 mixt of glycerol & (CH20H)2,
28% ~ & O.4% isopropylnaphthalene stdfonate)] NC 1.1 added and then AN 56.9, NaN03 12.0, oat
126)~tat Fran~is, FrP 980021( 1951) & CA 47, husk meal 2.0, waxed woodmeal 0.5, woodmeal
7779( 1953) [NC 30-40, NH4C104 40-15 & AN 1.0, S 2.0, starch 0.5 & chalk 0.3ps. The plastic
20-5 dried to a moisture content of 17%, malaxated props of the expl are lost if the phosphate ester is
(softened & mixed) at 80-85°, and sieved, after ~Y- omitted]
ing, to 1-2-mm particle size] 136)G.Kuhn & A. Berthmann, Gerp 903186(1954)
127)J.Taylor et al, BritP 670453-4(1952) & CA & CA 52,10581(1958) [Safety expl mixts contg
46, 10625( 1952) [Gelatin blasting expl for use 10% expl oil & 90% NaHC03/NaCl have little
 B 209

power, while mixts with more expl oil are not blasting assembly suitable for use in fiery or
safe. The expl oil content can be increased to gassy mines and having improved thermal and
17-18% w/o sacrifice of safety by addn of 4-5% storage stability: Mg(N03)2.6H20, AN &
A1Z03 hydrate ,or Fe203.3Hz0. These substances woodfIour. EIec fuses of BkPdr or a GuN mixt
absorb the expl oil and produce w upon deton, are used to ignite the chge)
which cools the reaction products. The combination 145)Etablissements John Kinsmen, FrP 1084121
of these two effects makes the additives superior ( 1955)& CA 53,5678( 1959)[Mining expl: AN(40-
to Glauber’s salt, talc or Si02] -mesh) 86, Sb203 (300 mesh) 4 & MgFe silicide
137)SGEC, FrP 1075474(1954)& CA 53,5678(1959) 10%1
(Safe, water-resistant, insens, nontoxid expl for 146)C.O.Davis et al, USP 2752848(1956) & CA
use in presence of firedamp: AN 84.5, DNT 14.6, w, 13444(1956) [NG-free blasting compn: AN/NaN03
& NC 0.9% mixed in a kneading mill. The some- mixt(contg 30-85% AN) 60, DNT/TNT mixt( l-5o%
what gelatinous prod of loading d 0.91-1 .34g/cc DNT) 10-30 & Fe silicon(contg at least 40% Si)
has a rate of deton 5250m/see, temp of expIn 0.5-10%. This compn has a packing d of 1.3-1.5
2030° & is insens to a No 6 detonating cap. After g/cc, may be initiated by a cap-sens primer to
1 hr immersion in w, the cartridges are insensitive give a deton vel of 3500-3900 m/see and has the
to a No 8 cap) same blasting strength as tamped dynamite. It is
138)SNF, FrP 1081803(1954) & FrAddn 66511(1957); less toxic, much Iess shock-sens and forms more
CA 53,5678 & 2080( 1959) [Mining expl for use in rigid cartridges than std Dynamite]
gassy mines: mixt of ground, foamed urea-HCHO 147)J.Taylor & T. J. Reid, BritP 743710(1956) &
resin/NaCl(45/55) 12, NG 11.5, NC 0.5, AN 53, CA 50, 14230( 1956) [Safety blasting expl: AN
NaCI 14 & NaNOa 9ps; or urea-HCHO resin-NaCl 53.1 & 11.9ps TNT are ground together and
foam 47, gelatinized NG(l/40) 23 & NH4N03 30p~ mixed with NaCl(thru No 60 sieve) 35ps. This
139)L.F.Audrieth, USP 2704706(1955) & CA ~, compn has a vel of deton of 2400 m/see and is
8208(1956) (AN 78.5-83.5, N2H4.HN03 5-10, TNT initiated by a No 3 coml’ MF detonator]
7.5, AI dust 0.5, coal pdr 0.3 & chalk 0.5%) 148)D.L.Kouba, USP 275 9807( 1956)& CA 51,
140)A.O.Franz, USP 2708623(1955)& CA 49, 719( 1957) (Semi-gelatinous expl: NG or NG+NGc
14326( 1955) (Expl for deep-well oil operations: 10-40, aromatic nitrocompd 5-30, hydrogenated
Pb salt of EDNA or in combination with other terphenyl 0.1-5, NC 50-80, inorg oxidg salt
heat-stable proplnts. This compd does not explode 50-80, carbonaceous material 1-12 & antacid 0.3
spontaneously below 300° and is relatively power- -lps)
fuI alone) 149)S.H.Davidson, BritP 757554( 1956) & CA 51,
141)Wm.H.Rinkenbach, USP 2709130( 1955) & CA 7722(1957) [AN (up to 95%) is coated with TNT,
49, 14325( 1955) [Blasting expl mixts of 1,1, l-Tris woodme aI & NaCI added, the I atter as fIame
(hydroxymethyl)-ethanetrinitrate 50-85 & 2,2-Di- -suppressing agent]
methyl- l,3-propanediol dinitrate 15-5070 are claim- 150)S.H.Davidson & T. Balfour, BritP 761396(1956)
ed to have lower fr PS & shock sensitivity, and to & CA 51,8438(1957) (AN 82, pod Al L bag-e
be more viscous and stable than mixts of NG & 8 & NaCl 8ps. This compn has a d of 1.04, power
NGc] 68% of that of Blasting Gelatin, and can be
142)G.P,Sillitto & A. Butchart, USP 271 1948(1955) initiated by a No 5-detonator)
& CA 49,12834(1955) [Gelatin Blasting expl which 151)A.Berthmann et al, GerP 938594( 1956) & CA
eliminates NC dust and the possibility of ignition 53, 1716( 1959) [Blasting expl resistant to humidity
by accidental electrostatic discharge is prepd by AN(coated with 0.05% Tetryl or O.04% Nitroisobutyl-
mixing 21ps wet NC(Nca 12.5% & ~0 ca 8%) glycerol) 79.5, NG 4, TNT 14, sawdust 2 & dye
with 75.5ps AN, 3 ps gl yceroI & O. 5ps oleic acid] 0.5%1
143)S.H.Davidson & G. P.Sillitto, USP 271366 152)W.MaxwelI & O. A. Gutton, USP 2789043(1957)
(1955) & CA 49,12834 (1955 )[Gelatin blasting expl & CA 51,9164(1957) [Blasting device constg of:
of reduced noxious gases & reduced eye and main chge-AN 55.0-75.0, Ca(OOCH)2 45.0-25.0 &
throat irritation suitable in hard-rock tunneling: Ca stearate 0-0.5%; discharge head AN (contg
NC 0.9, 80/20 NG/EGDN 25.5, o-kfNT 4.0, 0.05% acid magenta) 65.0, Ca(OOCH)z 34.9 & Ca
woodflour 2.5 AN 62.8, CaS04(anhydrite) 2.0 & stesrate O. 1%, packed in a tube in the center of
urea 2.Opsl which is imbedded a /use heating device- GuN
144)J.E.Williamson, BritP 724060(1955) & CA 60.0, K2S20~ 31.5, CU2C12 8.0 & petroleum jelly
49, 14325( 195 5) (A nondetong, gas-generating O. 5%, wrapped in fireproof manila paper and
 I

B 210

provided with an elec actuator. The blast takes 160)Poudreries R6unies de Belgique, SA, BelgP
placein4 sec when this device is usedin a 555262(1957) & CA 53,22955( 1959) [Powd safety
bore hole] coal mine expl: TNT 12, AN 69.5, NaCl 17 & Ca
153)J. E. Dolsn & P. B. Dumpster, BritP 769210 stearate 1.57. (or Ca stearate 1.0% and c=boxy-
(1957) & CA 51, l1720(1957)(@balanced blasting methylcellulose 0.5%)]
compn consisting of AN$ an org sensitizing agent 161)F.Lazzari, ItalP 558412(1957) & CA !53,719
& CaC03 ) (1959) (Gelatinized expl with stabilized sensitiv-
154)J.Alexander, BritP 777136(1957) & CA 51, ity NG/NGc 36, collodion cotton 25, AN 49.5,
14266( 1957) [Gelatin blasting compn: 80-20 cellulose 1, TNT 6 & PbSOq 5ps)
NG/EGDN 31.0, NC 1.6, o-MNT 1.0, alc 0.3, 162)1 .Fukuyama & H.Miyasue, JapP 8298(1957) &
woodmeal 0,5, AN 24.2, NaCl 21.8, finely milled CA 53,3698(1959) [Low Nti gelatin expl: AN
barytes 20.0, chalk 0.3 & (NH4)2HP04 0.3p. crystal with 3% KN03) 75, NG gel(contg 2% NC)
This expl is detonatable under hydrostatic press 10, starch & other combustibles 13 & H20 2%]
& is incapable of igniting flammable gases] 163)Soci6t6 Tunisienne d’Explosifs et de Munitions
155)Dynamit A-G, BritI? 781072( 1957) & GerP & P. Chaudron, FrP 1134326(1957)& CA 51,10062
938595 (1956); CA 52,732 & 15071(1958) [Noncak- ( 1957) (Expl for seismic exploration: RDX or
ing, water-resistant AN expl: nitrotoluenes 16.0, PETN 30% & AN 25% are dispersed in TNT)
AN 81.7, woodmeal 2.0, argillaceous earth(nature 164)A.Berthmann & G. Kuhn, GerP 1004983( 1957)
of clay) 0.1 & dye 0.2. Addn of 1% Tetryl improves & CA 54,13666(1960) (Blasting sheathed expl of
resistance to caking] increased flameproofness: core expl- gelatinous
156)Wm H. Rinkenbach & W. J .Carroll ,Jr, USP bIasting oil 11, TNT 2, woodmeal 3, NaN03 51.6
28145 55(1957) & CA 52,4184(1958) (Safe dry expl: & NH4CI 32.4%; and its sheath- blasting oil 10,
urea 16-21, AN 79-84 & kaolin or diatomaceous A1203 2 & NaCl 88%)
earth 1-3%. This compn is detonable by a No 16 165)E, J. Russell, USP 2821466( 1958)& CA 52,
cap and is equiv to 50% Dynamite) 6795( 1958) [Water-resistant semigel blasting expl;
157)Dynamit-AG, BritP 787387( 1957)& CA 52, AN 72, NaNOg 3.5, NS 20, l,l,l-Tris(hydroxy-
6795 (1958) { Noncaking expl of good storage methyl) ethane Trinitrate 1, carbonaceous matter
stability can be obtained by mixing NaNOg(coated 3 & chalk 0.5%]
with 1% Tetryl dissolved in benz) 80, NG 4, TNT 166)M.Scalera H M. Bender, U.SP 2826485(1958)
14 & woodmeal 2%. Another expl contained a mixt & CA 52,8560(1958) [Water-resistant blasting expl:
of NaNO~ & AN coated with Nitroisobutylgly cerol ] NG 7.8, AN 75, NaN03 4.3, NaCl 1,5, carbonaceous
157a)Dynamit-AG, BritP 78831 1(1957) & CA fuel 8.4 & polymeric mix~r,,ethylenebi sacrylarnide
52, 7703( 1958) { Expl compns obtained by mixing 3, acrylamide 95 & K2S20~ 2%) 3%. This compn
AN+NaCl with NG or NG/NGc. One or both salts is 3-4 times as w resistant as a similar compn
are coated with at least one surface agent, up to w/o the acrylamide mixt. An expl contg a copolymer
O.2% by wt of the salts. As coating agents can be of 10/90- acrylic acid/acrylamide 80 & A12(S04 )3-
used: Nitroisobutylglycerol, DNPh, Tetranitrodi- .7H20 20% also shows excellent resistance]
chlorodiphenylamin, Tetryl, HNDPhA, DNDPhA 167)A.Berthmann & G. Kuhn, USP 2829036(1958)
or silicone AK 100[a poly(dimethylsiloxane) & CA 52, 10581( 1958) [Fire-damp-proof expl:
having a viscosity of 100 centistokes]] NaN03(32% <0.lmm) 56.8, NH4CI(22% <0.lmm)
158)Poudreries R6unies de Belgique,SA, BelgP 35.7, NG 4.2, NGc 2.8 & argillaceous earth(clay)
553954( 1957) & CA 53,18487(1959) (Gelatinous or 0.5% gave a Pb block expansion of 79cc. An-
semi-gelatinous coal mine safety expl: expl oil other mixt: NaN03 (80% <O. lmm) 54.6, NH4C1
10, Si02 1.5, NaNOg 53.47, NH4C1 33.53 & atom- (80% <O. lmm) 34.4, NG 6.3, NGc 4.2 & argil-
ized Ca stearate 1.5%) laceous, earth O. 5% gave a Pb block expansion of
159)SAEPC, FrP 1133089( 1957) & CA 53,20807 8 lCC. Both expls were safe with a max chge of
( 1959) [Brisant coal mining expl device: igniter 16 cartridges in a single shot mortar against CH4
cbge- AN 70-80, NaNO~ 2-5, starch 1-5, cellulose -air mixtsl
3-6, Ca stearate 0.05, Sb2S3 0.01, S 0.05 ~ KMnOa 168)T.Sakurai, USP 2847291(1958) [Gelatin expl:
0.26% is activated by an elec bridge and develops AN 57.1, KN03 5, carbonaceous fuel 7.8, NC gel
sufficient press(80atm rein) to dec the main chge- 22-30 & konjak mannan gel(contg 8-12% H20)
AN 60-75, cellulose 3-7 & CaC09 10-20% which 8ps]
develops high gas press, suddenly released by 169)W.TaYlor et al, BritP 797! 12( 1958)& CA 53,
failure of a rupture disc, thus loosening coal] 1716( 1959) [ExpI for blasting under wet conditions

. _.-—. _ .—
 B211

or in strip mining of coal, rock or metal: AN(coated gives - 14.0; AN 95, (3-nitropropane 4.5 &
with 4% mineral jelly) 92 & Al powd 4ps mixed at (CH3)2C(NH2)CHZOH 0.5% gives + 11.5%; and
temp of 60-70°. This compn detonates in air at AN 80, @-nitropropane 18 & (CH3)2C(NH2)CH2-
3200m/sec and in cartridges possesses 87% the OH 2% gives an O balance of -14.9%]
power of Blasting Gelatin; it is detonatable after 178)Manufactwe G6n6rale de Munition, FrP
immersion under 10ft of w for I h] 11843 12( 1959) & CA 54,20210(1960) (In expls
170)N.Nakashiro & K. Takizawa, JapP 5849( 1958) intended for seismic prospecting, propagation of
&CA 53, 16540( 1959~ColIoidal expl: NC(ca 12%N) NG is facilitated by the introduction of small
is immersed in a dil aq soln of starch(or other hard inert particles, such as sand, Fe filings,
paste-forming agents) & mixed with 1/1 NG/NGc] crushed rock or corundum. Eg: NG 32.8, NC 1.3,
171)G.L.Griffith, Jr & D. G.Samuel, Jr, USP 2680041 AN 51.2, cellulose 3.8, BaSOa 4.7 & sand 6.2%)
(1958( & CA 53,3697(1959) [Blasting expl claimed
to be relatively insensitive and nonhazardous ate Blasting Explosives, Ammonium Nitrate.See Vol
obtained by mixing AN & NS with other ingredients I,p A341
Eg: AN 51.8, Na nitrate 16.1, Al pdr 2.7, Na car-
boxymethylcellulose LO, pecan meal 1.0, petroleum Blasting Gelatin(Dynamite Gomme A, Sprenga
oil 0.4, ZnO 0.3 & NS(contg 20% w) 33.4ps are gelatine, Gelatine Explosive) [See also Vol I,
thoroughly mixed to produce an expl of high strengt ~ p A 147(table)]
172) J. E. Lambert & I. O. Lewis, BritP 81OO45(1959) This is one of the most powerful coml expls. It
& CA 53, 10765( 1959) [Blasting chge for use in was invented by A. Nobel in 1875 and is still used
vertical boreholes: AN 86.5-94.6, Al pdr Up to extensively. It is prepd by gelatinizing 92-93ps
7.5 and meal up to 4% are introduced into the NG with 8-7ps coIlodion cotton(N 1 L 1 to 12.5%)
borehole and a nonexpl Iiq fuel (such as paraffin either by warming the ingredients(to 60-700) in a
oil or MNT) is added. The expl mixt is detonated water-j acketed vessel or by adding SOIVS, such as
with a primer cap] acet or ether-ale, to facilitate the gelatinization.
173)N.A.R.Bell & D.Storer, BritP 810046(1959)& Approx 0.2% of CaC03 is added as an antacid
CA 53,10765(1959) [Blasting chge for vertical and about 0.3% moisture is usually present in
boreholes consists of a 2-in core of HE’s mixt blasting gelatin. Lab prepn is given in Ref l(p
(such as NG, NC, woodmeal & waxed woodmeal) 226). The resulting gelatin is stiff and semi
in a cardboard container is surrounded by a sheath -transparent. This expl contains more NG than
of AN, 6“ in diam] any other and does not contain any inert in-
174)C.J.Breza, USP 2861875(1958) & BritP gredients except 0.2% CaCO~
821499( 1959); CA 53,4740( 1959)& 54,3957(1960) The following props are given in Refs 1 & 3:
(Blasting expl: AN 27, NaNOa 72, Fe silicon 24, Brz’sance(Kast’s method)- 148 x 106(86 x 106 for
stearic acid 0.5, TNT 23.2 & DNT 3.3ps mixed at TNT) or 172% TNT(Ref l,p 95); Heat P/ Explosion-
175°F and cast) 1610 cal/g at Cv and HZO vapor; Power- by Trauzl
175 )Poudreries R6unies de Belgique, SA, BelgP Test 520 CC(TNT 285) or 182% TNT(Ref 3); Spe-
573923(1959) & CA 54,3957( 1960).[Safety coal cific Energy- 12,285( TNT= 8,080) or 152% TNT(Ref
mine expl: expl oil 10, kieselguhr 1.5, NaN03 54.5, 3); Specific Volurne(Volume of gases of explosion
NH4C1 32.5, 75/25- polyethylene glycol/catboxy- at O 0/760 mm)- 711 l/kg(TNT=690)
methylcellulose 1.0 & stearinated chalk 0.5%] According to Berthelot, the equation for the
176)D.E.Pearsall, USP 2909418(1959) &CA 54, combustion of blasting gelatin cent aining 91.6%
5090( ~960) [O-sufficient combustible mixt for NG and 8.4% collodion cotton is as follows:
blasting & other applications: Ba02 79.5, KN03 51C3H5(N03)3 + C2aH~ ,01, (N03 )9=
5.6, Si 5.6, C(furnace black) 2.8, NC 6.0 & Al 177C02 + 143H20 + 81N2
stearate 0.5%, on blending with VOI esters or Temperature of Explosion- about 4450° (calcd)
ketones, drying granulating and coating with (Ref l,p 87); Vel o/ Deton at d 1.63,7500-7800
graphite, burns like BkPdr] n-Jsec, Diminution of Sensitivity Of Blasting
177)Commercial Solvents Corp, BritP 824533(1959) Gelatin. This expl in storage progressively hard-
& CA 54,8087(1960) [Safe blasting expl, with O ens with age and this is accompanied by a dimin-
balance -15 to + 15%, which can be prepd at the ution of sensitivity to initiation and by a consid-
site: AN 95, nitromethane(NMe) 4.5 & erable decrease in power as detd by Trauzl Test.
(CH3)2C(NHZ )CH20H 0.5 gives an O balance If stored for a long time the gelatin may misfire.
+ 15.75; AN 60, NMe 36 & (CH3)2C(NH2)CH20H 4% Such a gelatin can be ‘revivedn by heating it on
 I

B212

a water bath(to about 60-70°) and then cooling. powd considerably faster, sIightIy stronger, and
Another method consists of prolonged rolling of less hygr than NsN03 powders, but it is more ex-
the cartridge on a flat surface(Ref 9a). This phe- pensive. It is used principally in quarrying fine
nomenon of stiffening of gels with time is common dimension stone, granite and slate where the
but is not yet fully understood. TWO theories are shattering effect of dynamite is undesirable. This
briefly discussed under Ageing of Dynamites in powd is also used in the manuf of fireworks and
Vol l,p 111-L fuses
Re/s: l)Marshall 1( 1917), 365-8 2)Naoiim NG Re/s: Bebie(1943),36
( 1928),11 & 283-323 3)Vennin, Burlot & L;corch6
( 1932),552-3 4~ukharevskii & Pershakov( 1932), Blasting Powder “B”. A NaNO~ BkPdr the grains
150 S)Stettbacher(1933 ),87,95 & 225-6 6)Pepin of which are glazed with graphite to render them
Lehalleur(193S),328 & 324 7)Davis(1943),334 more moisture-resistant. It is slower, less power-
8)Bebie(1943),35 9)C.H. Johansson & A. Persson, ful, more hygr and less expensive than Powder
ApplSciResA4,295-304( 1954) & CA 48, 11789(1954) “A” and is used extensively for blasting purposes
(Rate of burning of blasting gelatin at different in non-gaseous coal mines, in stripping operations
temps & press) 9a)Dr I. A. Grageroff; private and in clay and shale
communication 1955) 10)Cook( 1958),9 Refs: Bebie(1943),36

Blasting Gelatin, Antifume. See Vol l,p A466-L Blasting Powder, Black See under Black Powder

Blasting Initiators(Caps), Electric See under Blasting Soluble Nitrocellulose, The same as Col-
Blasting Cap Iodion Cotton, It is used in blasting expls for
gelatinizing NG
Blasting Machine(called Ziindmaschine in Ger).
A device designed to supply current for firing Blasting Squibs, Electric. Elec squibs are devices
elec blasting caps. The device consists of a useful in igniting cleflagrating expls(such as BkPdr ),
wooden or metal case which encloses either a where the nature of the expl is such that it is
magneto or generator. The generator is driven by desirable to fire the chge by means of a flame,
a gear mechanism activated by either a plunger as distinguished from dynamites and other high
or a shaft extending from the top of the case. expls, which are initiated by the deton of expls
By pushing the plunger(or twist;ng the shaft) the contained in ordinary elec caps(see under Blasting
magneto or generator is made to rotate, developing Initiators)
110-300 volts of either alternating or direct The modern elec squib generalIy consists of an
current. The current is transmitted to a series ignition chge enclosed in a shell or tube of metal
of caps(as many as 100) by means of leading or plastic and an elec firing device. This device
wires and the chges of blasting expls are consists of two leading(leg) wires, passing through
thereby detonared. The plunger-type machines a mass of insulating material which closes the end
are called Push-Down Blasting Machines. of the cap, and are connected within the cap by
In large permanent operations, firing is sometimes means of a highly resistant wire(bridge) of such
done with current supplied by batteries or by diam that it is heated to incandescence when the
special electrical circuits connected to regular elec current passes through it. The bridge wire
power lines is ,surrounded(embedded in, or cemented in)
Refs; l) Meyer( 1943 ),334-5 2)Anon, “Ammunition by the “ignition composition”(see below) so that
Inspection Guide”, TM 9-1904(1944), 762 3)F.C. passage of the current through the wire causes the
Gibson & F .W.Brown, US BurMines RI 4136(1947) “ignition composition” to ignite, which in turn
4)Blasters’ Hbd( 1952), 106ff 5)Anon,Explosivst causes the deflagration of the priming chge. Wlhen
1954, 127-8( Blasting machine with millisec delay) the squib is thus fired, the flame plays upon the
blasting expl outside the squib
Blasting Oil. The name given to NG by A.Nobel. In the ordinary elec squib, the lower end of the
It is also called Explosive oil shell may be either open or perforated to allow
Re/.s: l)Bebie(1943),36 & 108 2)Cook(1958),8 the escape of the flame on ignition. In order to
prevent the access of moisture inside the squib
Blasting Powder”A” A KN03 BkPdr prepd in grains a stopper is sometimes provided to close the
of various sizes. The use of KN03 makes this ventholes. This stopper is removed just before
 B 213

-H=-do
—43
)

I-3
.+ b

Ventless Delay Instantaneous ~entless Delay

ELECTRIC BLASTING WJIBS

1 - Ventless metal shell 7 - Concave plug

2 - Base charge 8 - Bridge wire
2a - Lower base charge 9 - Electrical firing element
2b - Upper base charge (powd chge)
3 - Ignition charge 10 - Leading wire
4 - Metal carrier (tube) 11 – Leading wire
5 - Delay composition 12 - Waterproof layer
6 - Chamber 13 - Sulfur seal

the squib is used. Even with stoppers, these As the temp of ignition of the base chge should be
squibs are susceptible to the action of moisture. fairly high, special mixts were designed, such as
This is particularly undesirable in the so-called those containing finely divided Mg & Ba peroxide
delay squibs(see Note below) because admission or selenium, barium hydroxide & nitrostatch
of moisture through the vent may cause the delay
column to be damped out or to burn non-uniformly, The table on the following page gives
thus rendering an entire round of shots unsatisfac- examples of squibs proposed by Burrows &
tory due to deviation from the calctilated delay Noddin:
periods of one or more squibs in the group Instead of the base chges listed in the table, the
Note: Delay elec squibs differ from ordinary eIec foIlowing other combinations may be used:
squibs in that the firing element is separated a)combination of one of the powd metals, such as
from the chief deflagrating chge by a column of Zn, Cr, Cd, Fe, Co, Ni, Pb, Cu, As, Bi or Sb with
material having a uniform rate of combustion and oxidizers, such as permanganates, perchlorates,
serving as a delay element perforates, persulfites, peroxides, chlorates,
Burrows & Noddin of the DuPont Co (Ref 2 ) bromates and iodates; b)combination of Mg or Al
proposed using a ventIess(closed) s quib, aIthough with cyanides, phosphates, carbonates, sulfates,
previous attempts to produce such squibs[eg, that e tc
of Lewis & Woodbury(Ref 1)] were not successful. In addition to the ignition agents listed in the
Instead of providing the she 11 with weakeried table, the following may be used: Se and BaOz
portions of wall in the region containing the chge with either BkPdr, ground smokeless powder or
to insure rupture of the shell at such points of Turnbull’s Blue; zirconium with Ba02 or Bkpdr+
ignition, as was previously done, Burrows & NC(ca 12.7%N) + N-S
Noddin provided the base of the cap with a vent It has been claimed that the squibs listed in the
se sled with a disc of metal melting at the te m~ table are safe to handle and transport because
developed on ignition of the base chge in the cap, they are insens to impact and if accidently
 B 214

~ No 2 No 3

Base Charge 9 grains powd Ba02 87.5 10 grains powd CUO 75 Lower base chge
+ metallic Mg 12.5 + Mg 25 4 grains Ba02 88
+ Al 12%
Upper base cbge
4 grains Ba02 93
+ Al 7%
Ignition Charge 3 grains Ba02 78 + 3.5 grains Ba02 92 2.5 grains Ba02 78
Se 19+ nitrostarch 3% + nitrostar ch 8% +Se19+NS 3%
Delay Powder Ba02 85 + Se 15% No delay element, so Ba02 85 + Se 15% &
that the ignition chge traces of inert
is in direct firing material
relation with the
ignition compn sur-
rounding the bridge
wire
Concave Plug MF 51 + KCIO~ 23 MF 38.5 + KC103 38.5 MF 51 + KC103 23
Powder(sur- + NS 9 + charcoal 17% + NS 15.3 + charcoal + NS 9 + charcoal
rounding the 7.7% 17%
bridge wire)

ignited, they burn w/o producing an explosion employed in a squib having an ignition chge comp-
In a later patent(Ref 3), Burrows & Van Winter rising a loose blend of ground smokeless powder
of the DuPont Co proposed some modifications in 60 and BkPdr 40. A firing current of 0.330 amp was
delay elec squibs in order to prevent misfires found suitable for firing such ignition mixt. The
when fired in series. The inventors claimed that same wire was also found suitable for firing many
misfires in series may be practically eliminated other slow ignition mixts, such as ground smoke?
by selecting a bridge wire so characterized that less powd with a least one oxidizing agent such
the time required for its fusion is sufficiently as KC103, KN03, Ba(N03 )2, !3a02 and at least
greater than the period of initiation of the chge one finely divided metal(such as Al, Te, Se, Zr,
that certainty of firing in series is assured. For Mg, etc). Sulfur & Ca silicide may be substituted
the bridge, it was proposed to use wire of about for the metals mentioned above
0.0025” diam made of an alloy of Ni 80, Cr 20(in- Refs: l)H. A. Lewis & C. A. Woodbury, LISP 1964826
stead of a wire 0.0015” diam composed of an alloy (1934) & CA 28,5242(1934) 2) L. A. Burrows &
of Pt 80, Ir 20, as is customarily used. Although G. A. Noddin, USP 2123691(1938) & CA 32,
the Ni-Cr wire is satisfactory for any squib, it 7268(1938) 3) L. A. Burrows & C.B. Van Winter,
solves the specific problem for a squib containing USP 2228339(1941) & CA 35, 2722(1941)
an ignition chge capable of initiation by elec 4)Blasters’ Hdb(1952), 92
means, but which undergoes initiation so slowly
that misfires occur(when the Pt-Ir bridge is used)
when such chges are fired in series. Especially Blastite. A coml expl invented by Rosslyn & manuf
effective is Ni-Cr wire when the so-called”slow in Scotland in 1895, consisted of NC, glycerin ~
ignih”on charge” is used which is explained by vaseline
the inventors as “an ignition charge capable of Re/: Daniel(1902),74 & 694
being initiated by means of a standard Pt-80-Ir-20
bridge wire of 0.0015” diam but which undergoes Blast Meters. The measurement of air blast or
initiation so slowly that misfires occur when blast effects created by shock waves is made by
such charges are fired in series by means of such blast meters of various designs. Prior to WV711one
wires B type of blast meter consisted of a board provided
Other inventors state that the use of wire which with holes of different diameters across which
is slow to fuse is particularly advantageous whet. were pasted pieces of paper. In this so-called
 B 215

‘paper blast gage” the smaller the diam of the disc Bleiazid(Ger & Swiss). Lead Azide, described in
which is ruptured the greater the blast strength. Vol ~,p A545ff
Although this type of blast meter gives fairly ac-
curate comparative results, it suffers from the Bleitrinitroresorzinat or Blei styphnat(Ger & Swiss).
difficulty of maintaining its calibration from one Lead Trinitroresorcinate or Lead Styphnate, de-
series of tests to another and from the variations scribed under Re sorcinol and Derivatives
of temp & humidity (Refs 1 & 6)
Various improvements in the design of air blast Blend? US military grade NC prepd by blending
meters were made possibIe by the use of piezo-elec pyrocotton (N content 12.6-12. 7%)and guncotton
gages, tourmaline gages and Pb or Cu crusher (N ca 13.4%). The resulting mixt contains 13.15*
cylinders with suitable electronic amplifying de- 0.5%N
vices. It is possible with these devices to obtain Its prepn, props, tests & US Spec requirements
complete detailed records of the shock wave and are given under Nitrocellulose which is described
to compare peak press and impuIse values of under Cellulose and Derivatives
different expls. These blast meters are described
in various refs(Refs 2,3,4,5 & 9a). Schmidt(Ref 9) Blenders. See Mixing & Blending Equipment
discusses various experimental procedures used
for measuring blast effects
Philipchuk(Ref 7) has reported the use of the Blending. See under Mixing, Kneading & Blend-
Pendulum Gage, Foiimeter, S*’N TC(National Tubu- ing.
lcw Compartment) Gage & the Catenary Diaphragm
Gage for the measurement of free-air blast from Blending of Propel I ants. See under Propellants
bare expl chges. Jefferys et al(Ref 10) used th
ff3 Blast Gage for the measurement of air blast. Bi indage. (Fr) Armor; armor plate
The damage potentiaI of air & ground blast waves
and their measurements at long range are dis- Blind6 (Fr).Armored; bullet proof
cussed by Cook(Ref 8)
Re/s: l)Maj A. W. Ford, ArOrdn 7,222-4(1927) Blindici de. A B eIgian antitank(A/T) rocket
2)A.T.Ireland, USBurMinesTechPaper 635(1942) launcher similar to Amer Bazooka. It fires
(Design of Air-Blast Meter and Calibrating E qui- ‘Energa” rockets(see also under Belgian Ex-
pment),20pp 3)E.D.Wilson,Jr, OSRD Rpt 1153 plosives, etc)
(1943) 4)Anon,0Phi 40=34(1944) 5)S.SchuIman, Re/: E. Tomson, Li~ge and F. Lebrun, BruxeIles,
OSRD Rpt 5847(1945 & PBL 50829 6) W.A.Noyes, Belgium; private communication(1961)
Jr,Ed “Science in VW II(OSRD), Chemistry”, Little,
Brown & Co, Boston(1948),84 7)V.PhiIipchuk, Bloc de Plomb ou Bloc de Trauzl(fr). Lead
“Blast Evaluation of Bare and Cased Charges”, Block or Trauzl(Block) Test. See Coefficient
Initial Phase Rpt NN-P-30, National Northern Co, d’Utilisation Pratique(CUP or cup), VO1 1,
west Hanover, Mass(1955) 8)Cook(1958),365ff p IX-X
9)A.Schmidt,Explosivst 1959,225-31 & 1960,7-14
9a)Anon,0Ph180- 12(1959) (Air blast pressure Blockbusters. Very Iarge(up to 20 or more tons)
measurements, electronic) IO) R. C. Jefferys et al,
cylindrical bombs with extremely light case, strong
ARDE Memorandum(hIX) 54/60, ‘The hfeasurement
enough to withstand handling and shipping, but so
of Air Blast”( 15%0)
weak that no penetration is possible because the
case breaks upon impact. Such bombs are of very
Blast Wave or Burst Wave. See under !31ast Effects
high- capacity(c a 80%) and are fuzed for non-delay
in Air or superquick action. They must be dropped from
medium to high altitude so that impact near the
BLB. A cast double-base propellant developed at vertical is obtained, but without touching the
ABL. Its compn & props are in Conf “Propellant target. Their action is based on blast effect(qv)
Manual’’SPIA/h12( 1959), Unit NO 506 alone and they are capable of damaging areas,
particularly residential, as large as a block or
BLC. A cast double-base propellant developed at even larger. That is why they are called block-
ABL. Its compn & props are in Conf “Propellant busters (Compare with 3ombs, Earthquake)
Manual”SPIA/h12 (1959). Unit NO 507 Refs: l)Ohart(1946),204 & 227 2)PATR251O
 B 216

( 1958), Ger 192(under Structural Explosives) diethanol dinitrate or bis(2-nitroxyethy l)nitramine

in CA and diethanolnitramine dinitrate or dinitroxy-
Block Explosives. Certain expls such as TNT, ethylnitramine(DINA) in Blatt]
Tetrytol, RDX comps, NC & NS compns, when in III. 03 N. NH2(CH3 )CH2CH20N02 [called (/3-nitroxy-
the form of cast or pressed blocks, are called ethyl) methyl ammonium nitrate by us; not found
block expls. These blocks are usually used for in CA Index nor in Blatt]
demolitioit purposes IV. 02N.N(CH3)CH2CH20N02 [called 2-(methyl-
Re/: A. B. Schilling, PicArsn; private communica- nitramino)ethanol nitrate in CA and l-nitroxytri-
tion(1961) rnethylene-3-nitramine(MeNeNA) in Blatt] ]
Compds 1,11 & IV caused decreased blood
Block. Fitted Loading.See under Loading of Am- press; III was less active and caused tachyphylaxis.
munition No manifestation of chronic toxicity was observed
with either I or H
Blockholing. When it is necessary to remove Refs: l)J.Sal16, Th6rapie 8,565-77( 1953) & CA 48,
boulders or rocks deeply buried in earth, either a 5 369(1954) 2)J .Sal16, ArchInternPharamacody nam i e
‘snake-holing” or “blockholing” method is used. 98,355-61(1954) & CA 49,7115(1955) 3)J.Sall=,MP
Blockholing consists of drilling a hole about 1“ 36,305-7(1954) & CA 49,16218(1955)
in diam into the boulder(about half way), charging
it with dynamite and blasting. Drilling may be Blow. The slang word for an, expln, a severe deton
done with a hand-held hammer(j ack hammer). or any expl type malfunction that occurs when
Blockholing is also used in “secondary blasting” testing a rocket thrust chamber or similar rocket
and in blasting outcropping ledges, which are component
difficult to remove Re/: Rocket Encycl(1959),52
The DuPont Co recommends the use of ‘Red
Cross Extra”, 2(1~, for blockholing Blowback. An escape of gas under press to the
Re/: Blasters’ Hdb(1952),pp 329ff & 359-36o rear, on firing small-arms or fixed or semi-fixed
artillery ammunition, is called a blowback. This
Blocking and Block Breaking. Operations used in may be caused by ruptured cartridge, pierced
manuf of smokeless propellants primer, primer leak, blown primer or prime-r set
Re~.s: l)Hayes( 1938),22-4 2)TM 9-2900(1940), -back. The term also applies to the recoil of an
20-4 3)Th4 9~1904(1944),84 unlocked bolt in a firearm
Re/,s: l)Th4 9.1910( 1955),p 231 2)Glossary of
Blomen of Landing,NJ ,USA, patented in 1893 an 0rd(1959),39
expl prepd by dissolving in NG a product obtd by
the action of PA on an aromatic hydrocarbon Blowcase.See Acid Egg or Blowcase; Vol 1,
Refi Daniel(1902),p 74 p A88-I

Blood Pressure Lowering. The hypertensive effect Blow oil. See Oxidized Oil
of several expl compds has been reported by Sail:
(Refs l,2,&3). Dinitroglycerol, NGc, bis(hydroxy- Blown.out or Burned Shots. If dynamites(or other
methyl)nitroethane dinitrate, dimethylol nitroethane expls) are not properly detonated, they burn slow-
dinitrate, bis(hydroxymethyl)nitropropane dinitrate ly and incompletely i n the borehole, resulting in
& dimethylol nitropropane dinitrate were studied. so-called blown-out shots. Such shots are accom-
These compds were found to be vasodilators, less panied by the evolution of poisonous gases, such
active than NG but exercising a more lasting as nitrogen oxides, acrolein & carbon monoxide,
effect(Ref 3). Nitrated sorbitol has a vasodilator which are very undesirable in underground mines.
effect similar to hexanitromannitol( HNMnt) but As such shots do very little useful work, care
is S1 more toxic than HNMnt(Ref 2) should be t aken in prepg the charges to insure
The vasodilating props of some ‘new” nitro that the expl is properly primed with an initiator
derivs was detd on small animaIs(Ref 3): of sufficient strength to insure complete deton
I. 03 N. NH2(CH2CH20N02)2 [called di(P-nitroxy- Note: With properly detond dynamites, Principally
ethyl) ammonium nitrate in Blatt; not found in CA non-poisonous gases such as C02, N2 & H20
index] vapor are evolved
II. 02N.N(CH2CH20N02 )2[called 2,2 ‘-(nitroimino) Re/: Naoiim,NG(1928), pp279-80
 B 217

Blowout of Tracers. When a tracer compn is not thereby overcoming bomb-bay release problems
properly fixed inside the projectile cavity, the associated with tumbling or floating, and the
bomb will still retain its penetrating effectiveness
entire tracer mighr be e jetted intact from its
cavity shortly after leaving the muzzle of the gun. Re/: A. Berman, Picatinny Arsenal, Private Com-
As such blown-out tracers usually catch fire, they munication(July 1961)
might cause casualties among the firing gun crews
Refi H. E. Hirschland & S. Ricklin, Ordn 32,92(1947) Bluff.Shaped Munitions. Discussed in Minutes,OCM
(OrdComm Meeting),Item 361591(A-690),Project
Blue Cross Ammunition(called Blaukreuz in Ger), TA2-9111 ,26 April 1956(Conf)
The Germans, in grouping their chemical warfare
gases, applied a combination of military & toxi- Bluff Shaped Projectiles. The static stability &
cological viewpoints. Gases of their first grou~ drag characteristics of bluff, finless projectile
comprising the offensive gases(eg, tear gases) and bomb shapes were discus sed in a Iecture by
and the poisons causing such effects, were Loeb
called “green cross gases” (Griinkteuz). These Re/: A. A. Loeb,Testing Section Tech Lab Services
gases did not penetrate ordinary gas masks e- Lecture, PicArsn, 18 Sept 1956
quipped with charcoal filters
When this protection became available, the Blunderbuss(Streubtichse in Ger, which means
need arose for such gases which could penetrate scattering or strewing gun). It is an obsolete gun
charcoal filters, thus forcing the enemy to remove or firearm having a short barrel of rather large
rheir masks and inhale the gases of the first group, diam(up to 3. 5“ ), provided with a belled muzzle.
which were shot simultaneously with gases of the It was capable of holding a number of balls and
second group. This second group of gases was was intended to shoot objects at close quarters
designated by a ‘blue cross* and the poisons without exact aim
causing irritating effects were called “blue cross The weapons shooting several balls at a time
gases”. The prototype of these gases is diphenyl- were known as early as the middle of the 15th
arsinechloride, Protection against them, in the century but the gun resembling a real blunderbus
form of paper or cotton colloid filters, was almost was introduced in Spain in 1654 under the name
immediately developed and made available to ‘atcubus”. This was a matchlock arm. The later
troops models were provided with flintlocks and they
The third group comprised the defensive gases were used as late as the Igth c entury. Some
or “yellow cross gases” (Gelbkreuz). These gases blunderbusses were used in the navies. For
attained their putpose by persistency and, there- instance a number of blunderbusses were manufd
fore, contaminated an area for a protracted period in 1810 at the Harper’s Ferry Armory for rhe US
thus making it uninhabitable. The prototype of Navy(Ref 1)
this group is mustard gas Re/s: l)W.H.B .Smith, “Small Arms of the World”,
The purpose in using “green cross”, “blue cross” Military Service Publishing Co, Harrisburg,P a(
and/or “yellow cross” ammunition was to cause (1955),21 5 2)Glossaty of 0rd(1959),40
temporary incompacitation of the enemy personnel,
either immedy or within a short time BM Mixture. A smoke screen mixt constg of Zn
Re/: C. Wachtel, “Chemical Warfare”, Chemical dust, CC14 and relatively small percentages of
Publishing Co, Brooklyn, NY(1941),99 NH4CI, NaC104 & MgCO~. Since this mixt is
unstable it was replaced by a costlier HC Mixture
Blue Grass Ordnance Depot. US Ordnance Corps (w). Where long-time storage would not be neces-
field installation located near Richmond ,Kentucky
SW the BM mixt would be more economical than
the HC mixt. These mixts were used in pyrotechnic
Bluff.Shaped Bomb. A blunt-nosed bomb which ap- candles, mortar shells & grenades
proaches the configuration of a cylinder having Re/: H. W. Walker,IEC 1~, 1064(1925)
enclosed end flanges of two different thicknesses.
This configuration can be launched in a turbulent BM Powder or Poudre BM. French Naval Ordnance,
air region w/o tumbling and the bomb will ‘not Poudte B (M. marine= navy) made in the form of
‘ float” or remain suspended as a result of its lack strips, the sizes of which varied according to
of “lift”. Thus, a false bluff shaped outer configu- gun caliber. See under !3(Poudre ), item k(this VOI)
ration can be housed over a penetrating-type bomb
 1

B 218

for designations 13M1 to BM20 and other varieties Boboeuf Poudre. An expl similar to D.5signoHe
Re/s: I)Marshall 1(1917),297 2)Pascal(1930),226 Powder(qv)
Ref: Daniel(1902),76
BN Powder or Poudre BN. A modified(new) French
Poudre B(N= nouvelle= new) smokeless powd con- Bodewig, Jacob(1863-1 934). Ger scientist who
sisted of guncotton 29.1-38.7, collo”dion cotton specialized in military expls
41.3-33.2, Ba(N03)2 19.0-18.7, KN03 8.0-4.5, Ref: F. Lenze,SS 29,191-2(1934) (short biography
Na2C03 2.0-3.6 & VOI SOIVS 0.0-1.3%. Instead of & obituary)
soda ash, tannin was used sometimes. The powd
was gelatinized with eth-alc. Specific powds, such Body of Projectile. The cylindrical portion of a
as BN3F & BN3F, are described under B(Poudre) projectile directly behind the bourrelet(qv) and
Re/s: l)Daniel(1902),75 2)Gody(1907),638 extending to the rotating band is commonly called
3)Marshall 1 (1917),295 4)Weaver(1917), 134 the body. This portion is sl smaller in diam than
5)Bebie(1943),126 the bourrelet and is usually 1-2 calibers in length
Re/: Anon, *Ammunition Inspection Guide”, TM
BNF Powder or Poudre BNF. A new French 9* 1904(1944), 11
Poudre B rifle powd(F= fusil= rifIe). See under
B(Poudre), item m Bofors Detonating Cord or Bonocord. It consists of
Refl Marshall 1(1917),296 & 3(1932),85 a core of PETN contained within a woven tube of
cotton tlueads protected by an outer covering of a
BN Propellants. Liq BN monopropellants are plastic compn which is based on polyvinyl chlo-
described by T. D. Williams in Callery Chem Co ride or polyethene. Its outer diam is ca 5.5mm and
Conf Bimonthly Rept No 3(1960), Contract NO the quantity of expl is ca 12g per meter. Bonocord
a(s)58-454-d is usually examined for appearance, resistance to
cold, sensitivity to initiation, propagation of
Boattail. The tapered section at the rear(base) of detonation and velocity of deton, as described in
a bullet or projectile. Its purpose is to streamline Ref
the shell body so that air friction effects are re- Ref: Anon, “Analytical Methods for Powders and
duced and the stability in flight increased. A Explosives”, AB Bofors, Nobelkrut, Sweden(lxO),
boattail design is effective in this respect at ve- 207-8
locities less than 2900 ft/sec. When used in armor
-piercing bullets, the boattail design reduces the Bofors Industries(Aktiebolaget Bofors) of Sweden
no of cores(inside parts of bullets) broken during is one of the world’s largest companies manufg
penetration, caused by the base striking against expls, proplnts, ammo & weapons. It also manufs
the plate while entering the target(See also under machinery and equipment for the construction of
Bullets & Shells) plants for the manuf of the above items(for instance,
Refs: llHayes(1938),559 & 661 2)M.M. Johnson the plant for manufg TNT by the continuous method,
& C. T. Haven, ‘Ammunition. Its History, Develop- recently installed at Azul in Argentina) and many
ment and Use”, Morrow, NY(1943 ) 3)Anon, “Ammun- other items, some of which will be mentioned
ition Inspection Guide, “TM9~1904 (1944),14
below
4)Ohart( 1946),73-5 & 98
The parent company, the so-called AB Bofors,
is situated in the town of Karlskoga in the province
Bobbinite. Brit coa 1 mining expl constg of BkPdr
of Varmland( about halfway betw Stockholm and
mixed witli CUS04 & (NH4 )2S04 or starch and
0s10)
paraffin wax. TWO compns are reported: Type 1
The activities of Bofors Co date from 1646 when
KN03 62-65, charcoal 17-19, S 1.5-2.5, .(NH4)2S04
a royal charter was granted for the erection of two
11 & CUS04 1-6%; Type 2 KN03 63-66, charcoal
forge hammers in rhe mining district of Karlskoga.
18.5-20, S 1.5-2.5, rice flour 7-9 & paraffin 2.5
This smithy was gradually enlarged by the acqui-
-3. 5%. These compns are nondetong expls with
sition of other metallurgical plants located in the
moisture content of O-3.0% and d not exceeding
same district, and by the middle of the 19th
1.48 g/cc
century Bofors had developed into one of the
Re/s: l)Msrshall 1(1917),89 2)Barnett(1919),
largest iron works in Sweden. After its conversion
137-8 3) Pepin Leha11eur(1935),287 4)Thorpe 4,
in 1873 from private ownership to a limited company,
(1940 ),5 53 5)CondChemDict( 1942 ),288( not found
Bofors gradually expanded to include a blast
 B 219

furnace, an open-hearth furnace and a steel found- Bofors: NG & NC proplnts, TNT, PETN, RDX,
ry the latter being the first of its kind in Sweden. Hexotol(RDX/TNT), Hexotonal(RDX/TNT/Al),
In 1883, the Bofors Co began to manuf guns and initiating expls, plastic expls, gaines, detonators,
ammo in newly erected workshops. As the items detonating fuses; primers- electric and non-electric;
m anufd by Bofors were of first quality, they soon sbeiLs- HE, AP, star, smoke, mortar & incendiary;
established a reputation not only in Sweden but tracers, cartridge cases percussion tubes; bombs-
also in other countries. In 1894 the ownership of HE, flare & photoflash; rocket-propelled depth
!30fors was acquired by Dr Alfred Nobel, the charges; rockets- air-to- air, air-to-ground, flare &
famous inventor of dynamite and other expls and tsiget; guided missiles; guns- 20 & 57mm aircraft,
founder of the Nobel prize. For large-scale experi- fully automatic; 40, 57 & 120mm field, anti-aircraft,
ments, Nobel built a lab at Bjorkborn, situated ca fully automatic; 75mm to 210mm field guns, howitzers,
2km from the Bofors plant. A large-scale manuf of self-propelled, semi-automatic, hand-l ayed; 40mm
expls & proplnts was begun shortly after the death to 120mm naval anti-aircraft guns, fully-automatic,
of Nobel( 1896) and the works became known = power-operated( deck & turret mountings); 120mm to
AB f30/ors ~obelkrut( 1898). The manuf of armor 250mm naval turret guns, automatic, power-operated
-plate and fuzes began in 1900. With equipment (single, twin & triple mountings); 75mm to 305mm
acquired prior to WW I, Bofors was able to manuf coast-artillery, fully- and semi-automatic, power
guns up to 250mm in size. The plant was consid- -operated(movable and fixed mountings, turret
erably enlarged during WWI and an extensive mountings); launchers-depth-ch~ge & flare-rocket
proving ground was laid out. Since the end of the (fully autorhatic, power-operated deck guns with
economic depression following WWI(ca 1920) the machine-driven hoists); sewice G inspection
activities of Bofors have been continuously ex- equipment such as Doppler radar, acceleration
panding. New workshops were erected(arnong meters, condens ator chronographs, gas-pressure
them a subterranean one for the manuf of ammo) meters, apparatus for servo-technical control of
and new gun ctesigns were developed( among which poweroperated guns(such as transmitters, measur-
the well known 40mm Bofors Autornatlc Gun) ing devices, etc), devices for practice in handling
More recently, a new metallurgical plant, known mat6riel(such as loading training devices, practice
as Kilstaverken, was erected near Bofors and & sub-caliber guns and demonstration apparatus
extensive new labs were buiIt for metallurgical for machine laying)
and chemical research Re/: Aktiebolaget Bofors, Bofors, Sweden{ 1958)
In addn to expls, proplnts, ammo & weapons, (an illustrated booklet, published by Bofors Indus-
the Bofors Industries now manuf many items for tries)
industrial use, such as chemicals, pharmaceuticals, Note: History of Bofors AB given in conf VOI 3 of
high-alloy quality steels, castings and forgings. G. M. Chinn, “The Machine Gun”, Govt Prtg Off,
In 1958 it employed ca 8500 persons Washington,DC( 1953) was not used as a source of
Bofors Industries also own the following Swedish information
plants which are not located at Bofors or vicinity:
AB Tidabolmsverken, Tidaholm, founded in 1935 Bofors Plant Explosion(Sweden). On Dec 17,1940
(manufg machinery for producing plastics & plastic fire started in a wooden bldg used for shell loading
products) and contg 3 melt kettles of TNT as well as a num-
Nydquist & Helm AB (NOHAB), Trollhattan, ac- ber of loaded shells. After 25 min of burning, the
quired in 1936( manufg locomotives, rai~way cars, munition,b~t not the melt kettles contg TNT, ex-
water turbines & Diesel engines) ploded and scattered burning wood around the
AB W.Dan Bergmun(Wedaverken), S6dertiilje, neighboring build ings. This started a series of
acquired in 1939( manufg Al & hfg alloy castings new fires and explns which resulted in the de-
and light metal products) struction of 75 bldgs and a large amt of expls &
Ulvsunda Verkstiider AB, Bromma-Stockholm, munitions. The loss of life was comparatively
acquired in 1950( manufg grinding machine tools small( 11 killed) due to the fact that the explns
and hydraulic gears) were preceded by fire which gave sufficient time
These four plants employed in 1958 ca 4500 for most operators to escape
persons, which makes a total of 13000 for the Refi D. C. Westrell,SS 39,85-7(1944)
entire B ofors Industries
The following expls, proplnts, ammo, weapons Bofors Plastic Explosive(BPE) consists of PETN
and related items were manufd in 1958 by the AB mixed with mineral oi 1 by a special process. The
 B 220

expl is yel in color, has a bulk d of ca 1.45 g/cm3 Boiling and Condensation Temperatures, De
and is mouldable at temps below minus 15°. Its termination of . Boiling
is a state of ebullition
stability is of the same order as tryst PETN or the rapid change from the liq to the vapor
BPE is usually examined for appearance, cotnpw state. Condensation is the reverse process or
sition, consistency and moldability, matter insol the transformation of a substance from the
in mixt acet & CC14, acidity, mp of PETN and ex- gaseous to the Iiq state. The temp at which,
pIosion temp as described in Ref under atmospheric or other specified press, a
Ref: Anon, ‘Analytical Methods for Powders and liq is transformed into a vapor(or temp at which
Explosives”, AB Bofors Nobelkrut,Sweden( 1960), the vapor press of liq equals that of the surround-
206-7 ing gas) is called the boiling point. The temp Of
the reverse phenomenon is called the condensation
Bofors Propellants. A series of double-base propel- point. Apparatus & devices for detg boiling and
lants, known as NK(Nobelkrut), and manufd by the condensation points of substances are described
AI) Bofors Nobelkrut of Sweden. The so-called NK1 in the following Refs
was the ballistite(qv) invented by A .Nobel in 1888 Re/s: l) J. Barbaudy,’’Contribution iil’ftude des
(Ref 1). More recently, NK7, a solventless proplnt M61anges Liquides Ternaires”, Hermann,paris
has been used since 1931 in the Swedish(and other (1925) 2)C.Drucker in Ostwald-Luther, ”physiko
countries) army & navy. According to Admiral Alvaro -chemische Messungen’’, Leipzig(l93l); Edwards
-Alberto(Ref 5), its compn is: ~(sol) 70-64, NG Bros,Ann Arbor, Mich(1941) 2a)D. Quiggle et al,
24-29, “amilol’’+vaseline 5-7 & DPhA 1%. The “Apparatus for Boiling Point Range Measurements”,
term “amilol” is applied to amyl phthalate, a high IEC, AnalEd 6,466-8(1933) 3)V. Grign~d, ”Trait~
bp liq used as a gelatinize, which was first intro- de Chimie Organique”, Masson,Paris v1(1934)
duced by Nobel. Lundholm(Ref 2) claimed the use 4) A. Findlay, “Practical Physical Chemistry”,
of amyl phthal ate as an anti-erosive agent in Longmans-Green, London( 1941) 5)W.G.Palmer,
smokeless proplnts. His cornpns contd: a)NC 60, “Experimental Physical Chemistry”, Cambridge-
NG 30& diarnyl phthalate 10% or b)NC 60, NG 30, UnivPress, London (1941) 6) H. S. Taylor,
diamyl phthalate 5 & mineral jelly 5% “A Treatise on Physical Chemistry”, Van Nostrand,
Marqueyrol(Ref 3) analyzed some Bofors proplnts NY(1942) 7) J. Reilly & W.N.Rae, “Physico-chem-
and found that they contd NC(ll.9%N) 72.1, NG ic al Methods” ,VO1 1( 1943),PP 294-8 8)W.
22.8 & diamyl phthalate 5.1% Swietoslawski,’’Ebulliometric Measurements”,
Re/s: l)A.Nobel,BritP 1491(1888) 2)C.0.Lund- Reinhold,NY( 1945) 9)A.Weissberger,’’Phy sica1
holm,USP 701591(1901) & JSCI 21,927(1902) Methods in Organic Chemistry”, Interscience,NY
3) M.h4arqueyrol,MP 23, 178,300(1928) & MP 24,7 v 1(1945), pp 47-67 10)W. Swietoslawski, ”Deter-
(1930) 4)Naoiim( 1928),12 5 )Alvaro-Alberto, mination of Boiling and Condensation Tempera-
Admiral of the Brazilian Navy, Rio de Janerio(1958); tures”, revised version by WJ.Swietosl awski &
private communication(oct 1958) 6 )AB Bofors J. R. Anderson in 2nd Ed, v 1(1949),p~t I,PP 107
Nobelkrut, Wanual on Powders and Explosives”, -140 of Weissberger’s ‘ ‘Physical Methods in Or
Bofors,Sweden(1960), 169-90( Analytical procedure S) ganic Chemistry”, Interscience, NY
Boiling Point vs Latent Heat of Vaporization. This
Boghead Dynamite. NG 60-62% on pulver-
absorbed relationship for some secondary expls was investi-
ized boghead 38-40%. Boghead is a carbonaceous gated by Belyaev & Yuzefovich(Ref 1). The bp, ig-
rock or cameI with a high ash content, constg nition temp & latent heat of vaporization were detd
chiefly of Fe carbonate for several expls:
Re/s: l)Daniel(1902),76 2)Hackh’s(1944), 136
.- .——.— . ..——.. -—-------------
leg Point, ‘C at: [Ignitio=~G
Boilers, Steam and Steam This subject is
Power. Explosive \ 2mm [ 50mm 760mm Temp,°C cal/mol
discussed i n detail in Refs 1,2 & 3 and in other ( L -.! -
Methyl Nitrate ; - \ 5 \~’-~*ooo
books on boilers
Ethylene Din itrate 70 125 !, 197 19>230 i G500
Re/s: l) L. A. Harding, ‘Steam Power Plant Engi- TNT 190 24>50~ 300 295-300 ; .10700
neeringn,WiIey, NY(1932) 2)J.H.Keenan & F.G. PA 195 255 I 32.5 \30&310 6900
Keyes,’’Thermodynamic properties of Steam”, ITNB 175 250 \315\-! 7600
Wiley, NY(1936) 3)T.E.Butterfield et al, ‘Steam PETN 160 , 180 , 2(KI ! 215 \ 17300
and Gas Engineering ”, Van Nostrand,NY( 1947) NG , 125 180 ‘-_—_.245 j 200 “ / 7100
 B 221

This table shows that the ignition temp approx ton, were manufd in Spain(Refs 1 & 2). There is no
coincides with the bp at 760mm Hg, which indicates info available concerning presently used expls,
that flammability is preceded by the formation of a ammo or weapons
large amt of vapor which ignites when heated. Ac- Re/s: I)W.H.B.Smith, ‘The NRA Book of Small
cording to B & Y(Re f 1) TNT, PETN or PA neither Arms, v 2, RifIes”, MiIServP ubgCo, Harrisburg,P a,
detonates nor burns in vacuo, probably because the (1948),p 124 2)W.H.B.Smith, “The Book of Rifles’,
bp in vacuo is not near the ignition point. Their Stackpole Co, H arrisburg,Pa,2nd ed(1960),p 121
work was critically reviewed and questioned by
Ahrens(Ref 2) Bolle, Erwin( 1885(?)- 1938). Ger scientist who
Since the bp of solid & liq expls often is the specialized in ballistics. He worked for 35 years
highest temp occuring in the condensed phase dur- at the Chemisch-Technische Reichsanstalt near
ing combustion, it was attempted to det these con- Berlin and contributed numerous publications to
stants by extrapolation from bp’s detd at 15-20 & the science of expls & ballistics
80-100 mm Hg and by measuring the time r of evapn Refs: l)Anon, SS 33,334(1938) 2)W.Rimarski,SS
of droplets weighing 0.02mg, placed on metal blocks 34,226-7(1939)
kept at various temps T(abs). As a first approx-
imation Belyaev(Ref 3) derived the formula: Bolometer. A device for measuring minute quants
in r . (A /RT) + B, where of radiant heat by registering the change in con-
A . heat of vapzn and B = constant. From the above ductivity of a black body(Ref 1). It is used in
equation Belyaev calcd the following approx values: spectroscopy(Ref 2)
Re/s: l)Hackh’s( 1944),137 2 )A.Weissberger,
“Physical Methods of Organic Chemistry”, Inter-
Qvapzn science, NY, v 1,part 2(1949),pp 1426-28( article by
Explosive Boiling Point, ‘C kcal/mol
W.West)
Methyl Nitrate 66 9
Glycol Mononitrate 200 14 Bolovon O. Austrian Iiq expl constg of 41ps m-di-
TNT 335 17 nitrobenzene & 49ps 100% HN09. Either Fe or Al
PA 320 21 can be used as container material for Bolovon O
PETN 270 23 because the m-dinitrobenzene acts as an effective
RDX 340 26 inhibitor for HN03
TNB 315 18 Refi H. Horn& E .Fitzer, Berg u Hiittenmiinn Monatsh-
MNT 210 10 Montan Hochschule Leoben 98, 187-93(1935) & CA
DNT 2s0 17 48,372-3(1954)
Trinitrotrichloro benzene 270 13
Trinitrocresol 305 18 Bolton,F,(Sir). Proposed to chge cartridges made of
TNAns 310 15 cloth, with powd K nitrate(or other nitrate or chlo-
rate) and to soak them, just before use, in Iiq
Belyaev concluded that the Trouton const for nitrobenz or in a resin soln, molasses, etc. This
these compds is abnormally high, contrary to a compn and the process of mixing, in situ, are
surmise by Ahrens similar to that used in blasting expl Rack- a=Rock
Re/s: l) A. F. Belyaev & N. A. Yuzefovich, DoklAkad- (qv)
N 27,133-5(1940) (in English) & CA 34,7607(1940) Ref: Daniel(1902),76-7
2)H.Ahrens,SS 38,159-63(1943) & CA 38,2822(1944)
3)A.F.Belyaev,ZhFizKhim 22,91-101(1948) & CA Bolton Powder. A complex expl mixt, patented in
42,5227(1948) 1868 in England, consisted of NaN03, sugar, K
ferrocyanide, K2C03, alum, charcoal, ash, lime,
Bolivian Arms & Ammunition. As far as is known graphite & CUC03
Bolivia has no plants manufg expls, ammo or
Re/: Daniel(1902),76
weapons. The only info we have concerns some
rifles and carbines imported to Bolivia prior to
Boltzmann,L.( 1844-1906). Austrian physicist, who
WWII. Its 7.65mm Rifle, M1891 Mauser, was manufd
was professor at Graz, Munich & Vienna. Boltzmam’s
in Germany; the 7.65mm Rifles M1924 & M1934/30,
most important work was in mathematical physics.
Mauser, were manufd in Belgium and the 1 lmm
He made important contributions to the kinetic
single-shot Rifle M1875 & Carbine Ml 879, Reming-
theory of gases and published papers on what is
 I

now known as Boltzmann ’s H. theorem& on Maxwell’s iron bars surrounded by rings or hoops which
electromagnetic theory (See also Boltzmann’s Con- were driven over the bars while red hot and shrunk
stant and Boltzmann’s Law) into place as they cooled. The bombards were
Re/: EncyclBritannica, 14th ed,v 3(1929),p 829[Bi- usually short and sometimes had a large tapering
ography not listed in v 3(1952)] bore with a powder chamber smaller than the bore.
In appearance, if not in use, the bombards were
Boltzmann’s Constant. A molecular constant in the prototypes of the true mortars, which apparently
thermodynamic calculations of the energy of a were invented in Germany ca 1435(Ref 3). Accdg
single molecule or oscillator. It is expressed by to Greener(Ref 1, p 18), some bombards were made
k = R/N, where R is the gas constant per mol and of solid stone, being hollowed out until of suf-
N is the Avogadro number. Its value is 1.380 x ficient depth to hold the chge of BkPdr; and it is
10-ls erg per ‘c probably that the term “mortar” originated from
Refi “The Van Nostrand Chem ists’s Dictionary”, these weapons. Later types of bombards were made
Van Nostrand, Princeton(1953),p 90 of wrought iron. A wro ught-iron bombard which threw
a stone weighing ca 1601b is shown on Plate I, in-
Boltzmann’s Law. The law of the equip artition of serted betw pp 469A & 469B of Ref 2
energy to a molecular system. 5tefan-Boltzmann Re/s: 1 )W. W. Greener, “The Gun and Its Develop-
Law states that the total energy radiated from a ment”, Cassell, Peter, Galpin & Co, London(1881)
black body is proportional to its absolute temp 2)EncyclBritannic a 2(1952), under Artillery
raised to the fourth power. It is expressed by 3)Collier’s Encycl 2(1957),295, under Artillery
E = u (~ - ~ ) where E = total energy in ergs,
T = abs temp of the source, To = abs temp of the Bombard (verb). To attack, formerIy with bombards,
surroundings, and a = Stefan-Boltzmann const, now with any weapons hurIing expI shells, bombs,
which is 1.36 x 1012 cal/sec/cm2 of black body grenades or rockets. Also to subject(a body) to the
surface impingement of small p-titles or rays
l?e~: The Van Nostrand Chemist’s Dictionary, Ref: Merriam-Webster’s( 1951),305
Van Nostrand, Princeton(1953),421,429 & 663
Bombardelle. A crude early firearm consisting of
Bomarc. An Air Force surface-to-ah interceptor a tube on a long shaft
-type homing missile, traveling at supersonic Re/: Merriam-Webster’s( 1951),305
speeds. It has long range, uses a Iiq fuel plus
two ram jet engines and has command radar guid- Bombardment. A sustained attack upon a city, for-
ance tification or troops in position with bombs, shells,
Re/s: I)Glossary of 0rd(1959),41 2) F. I. Ordway rockets or other missiles. The primary object of
& R. C. Wakeford, ‘International Missile and Space- bombardment, preliminary to assault, is to destroy
craft Guide” ,McGraw-Hill,NY( 1960),20 (USA) the defenses, to destroy or neutralize the weapons
of the enemy and to demoralize the troops
Bomb. See BOMBS Also, the action of bombarding atomic nuclei
with rays or small particles
Bomb, American(lnitiating Device for). Amer aerial Re/s: l)EncyclBritannica 3(1952),829 2)Glossary
bombs are initiated by nose and/or tail fuzes. of 0rd(1959), 41
There is also in some bombs, the transverse fuze
which is fitted into a cavity of the body at right Bombardment FIares. Pyrotechnic bombs designed
angles to its axis. The latter type of fuze, when to provide illumination for night bombardment. Sev-
used in depth bombs, is activated by pressure of eraI types of such flares are described by Ohart
water(hydrostatic, also called t~warts~ip fuze) ( 1946),3 15-16. See also Bombs, Pyrotechnic, under
Ref: A. B. Schilling, PicArsn,private communication BOMBS
(1961)
Bomb BIast. The blast that results from the expln
Bombard (from the Ital Bombo e ardore, meaning of a bomb
thunder & lighting). A medieval( 14th century) piece Ref: Glossary of 0rd(1959),41
of heavy ordnance used for throwing heavy, round
stones and Iater for iron shot. The first bombards Bomb, British(Initiating Devices for). Brit initi-
were made into circular bundles of longitudinal sting devices for bombs are divided into two groups:
 B 223

pistols and fuzes. The term pistol is used to de- (1959),42

scribe an initiating device which contains no expl
components(primer, detonator or booster) as it is Bomb Destruction. See Bombs, Destruction of, in
normally shipped or issued. It is purely a mech section which follows BOMBS
device, embodying certain arming and safety fea-
tures for initiating expl components which are Bomb Disposal. See Bombs, Disposal of, in section
inserted in the bomb as a separate entity. These which follows BOMBS
separate expl components used with the pistols
are called detonators. Initiating devices which do Bomb Drop Test (Bomb Functioning Test). See
contain expl components as integral parts, howeveq Vol l, Physical Tests,p VIII
are termed fuzes. Generally; in addn to a primer
-detonator combination, fuzes are also fitted with Bomb for Determination of Heats of Combustion and
burster charges or boosters. As a general rule, Explosion. See under Calorimetric Tests
pistols are used to initiate HE bombs, while Brit
fuzes are employed in miscellaneous types of mis- Bomb Functioning Test. See Bomb Drop Test in
siles, such as smoke bombs, flares, etc. In most Yol l,p VIII
bombs of 500-lb and under in wt, pistols are
screwed directly into an exploder container Bomb Fuze. See under Fuzes
which holds a detonator and booster pellets.
In bombs weighing over 500 lb, the pistol is screw- Bomb Handling. See under Bombs, Packing, Storage,
ed into a detonator holder which, in turn, is thread- Handling, etc
ed into the exploder container of the bomb. In this
size of bomb, if a fuze is to be used, the detonator Bomb High Explosive Trains(Used during WWII.
holder is omitted and the fuze is screwed directly The systems used in various HE bombs are briefly
into the exploder container described in All&EnExpl(1946 ),pp 164-9(See also
Ref: A. B. Schilling,PicArsn; private communication Fig)
(1961) American HE bombs of W WII were equipped in
most cases with an impact fuze and the train con-
Bomb Calorimeter or Closed Bomb. See under sisted of the following components:
Calorimeter, Calorimetry and Calorimetric Tests A. Primer, Percussio~ Type:
a) Instantaneous Ac-
Bombcannon of Krupp (Die Krupp’sche 5.3-cm tion- LA primer compn
Bombenkanone, in Ger). A cannon which could sensitized with LSt;
shoot large bombs in a manner similar to rifle used with a needle-type
grenades. A detailed description is given in the firing pin
Ref b)Delay Action- MF/-
Re/: Maj Berlin,SS 5,285-88(1910) KC103/SbzS3(w or w,.6
abrasive such as ground
Bomb Carpet. The fall of bombs, during so-called glass or Carborundum)
carpet bombing, in a creeping pattern to cover the compn; used with a
area as with a carpet blunt firing pin
Re/: Glossary of 0rd(1959), 41 & 56 B. Delay Element:
BkPdr or, in dive bomb-
Bomb Complete Round. lt consists of all the com- ing, BaCrOa was ig-
ponents necessary to drop and function the bomb. nited by the flame from
The usual components are: body with filler(con- a percussion primer
stituting the payload), fin(or parachute) assembly C. Relay- A cup of LA
(to stabilize the bomb in flight), fuze or fuzes(to covered with onion
function the bomb at the proper moment) and arm- skin paper; it was ig-
ing wire assembly. These components are usually nited from the flame of
assembled in the field just before the bomb is the primer or of the
hoisted into the bomb bay of the aircraft, except delay chge and deto-
in the case of small fragmentation bombs Bomb Explosive Troin n ated with sufficient
Re/s: l)Ohart(1946),7 & 216 2)Glossary of Ord power to initiate the
detonator
 B 22.4

Note: Since the detonator was enclosed in a lindrical metal containers which were open at the
metallic case and was not in close contact top and at the bottom
with the delay, the relay was necessary to in- G. Bursting Charge- Amatol, Ammonal, Cyclotol or
tensify the flame from the delay. In the case of TNT
instantaneous fuzes, the delay was by-passed Japanese HE bomb train usually consisted of the
and the relay was initiated directly from the following components:
primer A. Primer- MF composition(Bakufun and Raibun)
5. Detonator. It consisted of an upper or primary w/o abrasive; firing pin was generally the needle
chge(LA sensitized by LSt) and a lower or base -type
chge sometimes called the sub- boos ter(Tetryl). B. Delay- BkPdr(Yuenyaku or Kokushokuyaku)
The relay detonated the upper chge and its action ~ Relay- BkPdr
was intensified by the lower chge which, in turn, D. Detonator- LA(Chikkaen) in an open container
would detonate the booster(see below) E. Sub-booster- generally Tetryl(Meiayaku)
Note: For instantaneous fuzes, the primer and F. ,Booster- pressed PA(OshokuYaku) x RDX
upper & lower detonators were enclosed in a (Shouyaku) (in some smaller bombs)
container forming the so-called prz”rner.detonator Note: An auxiliary booster with pressed Type 98
E.Booster. It consisted of a large amt of Tetryl Expl(70/3 O-TNAns/HNDPhA) was used in the tail
enclosed in a cylindrical contai ner of larger bombs
F. Burster or Main Charge. It consisted of a fairly G. Bursting Charge- PA(pressed or cast), TNAns
insensitive HE, such as TNT, Amatol, Expl D, (Type 91 Expl), Type 98 Expl, Cyclotols(Nigotanoy-
Comp B, DBX, Torpex or Ednatol which could not aku-Mk2), 25/75-TNT/PA mixts(Chaoyaku), 75/2 5
be initiated positively by a detonator alone -AN/RDX (Angayaku) and 50/ 50-Am atol(Shotoyaku)
British HE bomb train of WWII consisted of the
following components: Bomb Inspection. See under Bombs, Packing, Storage,
~ Primer. It contained either LA or hfF composition etc.
B. Delay. It consisted of a BkPdr safety fuze
c Relay. It contained BkPdr Bomb Loading. See under Bombs, Packing, Storage,
CL Detonator. It contained either LA sensitized etc
with LSt or 80/20-MF/KC103 compn
Note: All the above components were enclosed in a Bomb Maintenance. See under Bombs, Packing, Stor-
metallic tube and the ensemble was known as a age, etc
detonator. For instantaneous action the delay and
relay could be eliminated Bomb Manometric. A manometric bomb is a device
Ew Exp loder(Booster). It consisted of compressed for measuring the pressure developed on expln and
Tetryl or a combination of compressed Tetryl/TNT. of some other props of expls and proplnts. O ae of
The detonator tube was inserted in the exploder the best known devices is the Bicbel Bomb, briefly
(See also Bombs, British, Initiating Devices) described in Vol 1, p VIII
FM Bursting Charge. It consisted of one of the fol- Other devices include the Vieille Bomb, Mano-
lowing HE ‘s: TNT, Amatol, Cyclotol, Pentolite, metric Crusher Bomb of the “Commission des Sub-
Minol H, Baratol, DBX, Amatex, Torpex, Shellite stances Explosives”, Petavel Manornetric Bomb,
or Tritonal Manometric Piezoelectric Bomb, Krupp Bomb, etc
German HE bomb train of WWII is described in Refs: l)Marshall 2(1917),4445 2)Marshall 3
PATR 2510( 1958),p Ger 20 (1932), 133 3)Vennin,Burlot & L~corch6(1932),
ion HE bomb train usually consisted
Italian of the 72-87 4)Muraour(1947),83 -90 5 )A.Douillet &
following components: P. Miaud,MP 36,277-84 (1954) (Studies of burning
Au Primer- MF composition of BkPdr bags by means of manometric bomb)
B. Delay- BkPdr 6)G.Seitz,Explosivst 1955,173-8 & 201-6(Investi-
C. Relay- BkPdr gation of the burning of proplnts in a Vieille bomb)
D. Detonator- LA sensitized with LSt 7)P .Miaud,hfP 38, 181-8(1956) (Installation permit-
E. Sub- booster(also called auxiliary booster)- pres- ting ignition of a proplnt in the Vieille-type mano-
sed RDX metric bomb by means of a gaseous mixt and ex-
F. Booster(also called main booster)- pressed TNT tinction of burni ng in the course of combn at a
(See also under BOOSTER) desired moment)
Note: All of the above components were held in cy-
 B 225

Bomb Packing. See under Bombs, Packing, Storage, Norton & CO, NY(1959)
etc
BOMBS
Bomb, Plastic (Bombe in Fr, PIastik-Bombe
plastique (Bombe in Fr & in Ger, Bombs in Ital, Rus & Span)
in Ger), Accdg COdescription given in “Die Welt- A bomb is a hollow metalIic, concrete, plastic or
woche”, Ziirich, 14 April 1961, abstracted by Dr glass vessel of various shapes and sizes fiHed
Langhans in ExpIosivst 1962,22, a “pIastic bomb” with either an expIosive, a poisonous substance,
usually consists of a plastic mass made into shape an illuminant or smoke-producing compn. Bombs
of a bomb or any othe r desired shape. Its compn used before the invention of airplanes and subma-
varies from a GeIatindynamite to plastic expfs rines were mostly in the shape of spheres or cylin-
based on TNT, PETN or RDX. Such a bomb can be ders and were either thrown by hand(such as a band
easily detonated by a blasting cap, but it is prac- grenade or arzarc~ist’s bomb) or placed inside or
tically insensitive to impact, friction or moderate underneath an object intended to be destroyed(such
heat. The plastic mass can easily be molded into as a demolition bomb with a time mechanism). With
any desired shape and can be attached to a target the invention of dirigibles, airplanes and then heli-
by sticking like chewing gum. Such a bomb can be copters, there appeared bombs which could be drop-
easily transported or carried around hidden under ped from aboard them(aerial bombs); and with the
clothing invention of submarines there appeared bombs which
Note: Plastic bomb was also described by A. Stett- could be dropped from aboard a ship or boat against
bacher in ‘Tages-Anzeiger fiir Stadt und Kanton, a submarine(depth bomb). This bomb may also be
Ziirich, 20 April, 1961 dropped from aboard a plane, dirigible or helicopte~
The most important of these are aerial bombs(bombs
Bombrini Parodi.Delfino Plants. See Societii Anonima for aircraft)
Bombrini Parodi-Delfino under Italian War Plants Historical. Attempts to release bombs from the air
were made after the balloon (’faerostate”) (invented
Bomb Safety Precautions. See under Bombs, in 1783 by the hiongolfier in France) began to be
Storage, etc used for military purposes. One of the first of such
attempts was made in 1849 during the battle betw
Bomb Shipping, See under Bombs, Packing, Storage, the Austrians & Venetians. When the wind was in
etc the “proper” direction(blowing towards Venice) the
Austrians attached small bombs, provided with
Bomb Storage and Surveillance. See under Bombs, time fuzes, to paper balloons ke’pt aloft by means
Packing, Storage, etc of heated air. When released, the balloons lifted
the bombs to an altitude of ca 30 ft and drifted
Bomb Tests. The usual procedures for proving towards the city. When well within it, time fuzes
ground tests of bombs and related items may be exploded the bombs. Little damage re suited but
classified as follows: hard surface test, functioning, the psychological effect was great. In the latter
fuze, arming wire, primer, detonator, adapter booster, part of the 19th century several attempts were
.burster, accuracy of bombing, bomb explosive, ‘para made to drop ,bombs with the help of crews, from
chute units, chemical, pit, high & low panels and observation balloons . This practice was discon-
range bombing tests. The tests are described in tinued in 1899 because it was forbidden by the
the Ordnance Proof Manuals, Aberdeen Proving Hague Convention [See also Balloons and Air-
Ground, Maryland, Nos 9~11 (1949) and Nos 1040 ships and Their ,Application in war]
(1957) In 1903, the Wright brothers constructed a
successful airplane and in 1907 the Hague Con-
Bomb Transportation. See under Bombs, Packing, vention’s restriction against dropping bombs
Storage, etc from the air was Iifted. By 1910, miIitary author-
ities of all the major powers began experimenting
Bomb, Unexploded (UXB). A bomb which fails to with planes, but at first the apparatus was regarded
expI on impact or immediately thereafter. It is rather as a more efficient means for gaining info
considered to be a delayed action bomb until the in the field than for dropping bombs. The earliest
contrary is proved recorded use of bombs dropped from a plane was
Ref.s: Glossrity of 0rd(1959),44 2)A.B.HattIey, by the Italians ca 1911 during the war in Tripoli.
“Unexploded Bomb, A History of Bomb Disposal”, These bombs were makeshift equipment, dropped
 B 226

by hand over the side of a plane. The bombs had electrical bomb fuze proved to be very successful
no fuzes because they were filled with NG, which and its further development and improvement were
exploded by itself on impact ordered in anticipation of WWII
Before WWI, the two countries who seem to have The use of aeria[ bombing in WWI and the result-
devoted the most time and money to aerial bombs ing damage, on both sides, were insignificant in
were Germany & Spain. They developed bombs comparison with what was done during WWII, when
specially designed for use from aircraft. The bombing became a most important weapon, espe-
Spaniards were the fhst to employ a bomb with cially for the US and GtBritain. Because of great
mechanical fuze incorporating safety devices improvements in aiming devices it became possible
to protect airmen launching it. This was during to achieve very precise bombing and to hit only
the war in Morocco targets of military importance. However this was
During the first few weeks of ‘$’WI, planes were not always done and many historical bldgs(such as
not equipped with guns or bombs, because planes in London, Miinich,Niirnberg, Berlin, Heidelberg,etc)
were used only for observation purposes. Th same or even entire ancient cities(such as Caen, in
might be said about dirigibles. At the end of the Normandy or Dresden & Wiirzburg in Germany) were
first 3 months, however, all the belligerents had destroyed. Some of these places were still in
organized squadrons to drop bombs. The first ruins as recently as the summer of 1961 and those
aerial bombs were dropped, by the Germans, Aug which were restored do not look exactly the same
30, 1914 on Paris. Only one plane was involved. as before the war
One of the bombs penetrated a crowded subway Not only were aiming devices improved but more
sta, killing or mortally wounding ca 1000 persons. precise and deadly bombs were developed. The
The other countries started to follow the German size of bombs was increased until wts of ca 20tons
example. The Germans also used Zeppelins to were reached. Some of the biggest bombs were
some extent, especially in night raids o,. London. known as block busters because the force of
The first aerial bombs were modified shells(such the blast of a single bomb could destroy an entire
as 3-in or 75-mm), equipped with fins and fuzes. block or more(Refs 1,2,3,4 & 5). Another term
As there were no sighting apparatus and no bomb used was eartbqziake bombs
racks, the aiming could not be accurate. Great Toward the end of WTII, a so-called atomic bomb
improvements in construction of planes and of (see Vol l,p A499-L) was developed in the US and
aerial bom’bs were made in the course of WWI and used against two Japanese cities(Hiroshima &
by the end of the war the aiming became very Nagasaki, Aug 1945), killing thousands of civilians
accurate. It became possible to bomb strategic and probably some soldiers. Many more civilians
objects without touching historical bldgs, especial- were injured and still more were invalided due to
1~ churches, castles, palaces, etc. Special purpose radiation. The use of these atomic bombs resulted
bombs, such as demolition, fragmentation, chemical, in the end of the war with Japan and thereby saved
incendiary, illuminating, propaganda, etc, made the lives of numerous American personnel
their appearance and the size of demolition bombs A still more powerful and dangerous bomb(hydrogen
gradually was increased from 45-lb to 122-Ib and or thermonuclear bomb) was developed in the US
then to 230-lb. The fragmentation bombs of WWI after WWII, The British, French & Russians now
were the British 25-lb. Some other bombs were of have the capability of manufg atomic & hydrogen
French design but none of Amer design were used: bombs and eventually all nations may possess the
the US Armed Forces used Fr & Brit bombs. AI- secret
though quite a number of such bombs were manufd An ingenious method for “bombing” the USA with
in the US in the latter part of mI, none of them the aid of paper balloons was used by the Japanese
reached the front in time to be used. The most during WWII [See under Balloons and Airships and
spectacular success of WWI was the bombing of Their Application in War]
the Turkish Army by Brit Gen AIIenby
Considerable aerial bombing took place during Bombs for Aircraft(Aerial An aerial bomb
Bombs).
the Spanish Civil War( 1936-9), mostly by the is a type of ammo designed to be dropped from an
Germans, who sided with France. The opposing aircraft in flight to inflict damage on the enemy or
Spanish faction was helped by the USSR, who to serve a special pt~wpose such as target identifica-
supplied some ~med airplanes and pilots. This tion or provision of a light source for photography
war gave opportunity, especially to the Germans, A bomb consists usually of a metal container filled
to test the efficiency of newer bombs. The Ger with expls or c hemicals, a device for stabilizing

1 -.
 B 227

its flight so that it can be aimed accurately, a Some bombs are carried in racks. Other bombs are
mechanism for explg the bomb at the target, and assembled in clusters for dropping as a unit. (See
such safety devices as may be necessary to make Fig), Methods of stabilizing bomb flights are shown
the bomb safe to handle. The metal container, cal- on Fig
led the bomb body, is usually stream-lined with a According to TM 9-1900 (Ref 15), the current US
rounded(ogival) nose and tapered tail. The stabiliz- bombs may be classified: a) according to filler- as
ing device is attached to the tail end of the body explosive, chemical, incendiary, pyrotechnic G
and generally consists of a sheet metal fin assembly, inert and b) according to use- as armor. piercing(AP)
although a parachute uni t, a sleeve or cloth streanr semi- arrno~piercing( SAP), general purpose,
ers may be used. The mechanism for explg the chge light case(LC), fragmentation(F), depth(D), gas,
is caIled a fuze and is generally placed in the nose smoke (or screening smokes ), incendiary(l), pboto-
or in the tail end. of the body. Two or more fuzes /lash, target identification, Ieafle t, practice,
(one in the nose and one in the taiI) are occasional practice- target and dummy
Iy used in the same bomb for different effects, for A slightly different designation was given for
flexibility in use, or to insure reliability of function - British bombs used during WWII, such as:
ing; that is, should one fuze malfunction, the other F(fragmentation) (charged with amatol, TNT or
will cause the bomb to explode cYclotol), GP(general purpose) (chged with Amatol
or Cyclotol), MC(medium capacity) & HC(high
capacity) (both types chged with Amatol, Amatex,
TNT, Pentolite, Cyclotol, Torpex 2 or Minol 2),
} Dp(deep penetration) (chged with Torpex), SAP
~~~>(semi-armor-piercing)(chged with TNT), AP
(armor-piercing) (chged with “shellite”, see VOI
l,p Abbr 47), AS(antisubmarine) (chged with TNT,
Cyclotol, BaratoI or Torpex; some bombs with
shaped charge effect), DC(aircraft depth charge)
(chged with Amatol or Torpex), B(buoyacy)(chged
“r/ - Cluster
with Torpex 2), [(incendiary),
chemical), lT(infantry training,
LC(Iight
Tl(target
case
identifica-
tion), AT(antitapk) (one of such bombs contained
Safety devices “Nobel’s Explosive N 0808° with shaped chge
are usually effect), Smoke(smoke) and Practice (practice).
built into the Most of these bombs corresponded in their use to
fuze and are US bombs. The so-called DP bomb was designed
held in place to give deep penetration of the earth and to produce
during storage heavy shock waves as a result of expln of its main
and shipment by chge. Their chge/wt ratio was ca 43%. The B(buoy-
seal wires or ancy) bomb was designed to be dropped in front of
cotter pins. ships underway and to rise SKI detonate on cent act
When the bomb with the ship’s bottom. Its wt was ca 2501b
‘,,,

\:i,“ “1
VAM T :“ ,, ‘ The designation of German WWII bombs is given

i?
,1 is prepd for USG
the seal wire in Refs 11 & 16, that of French and Italian. bombs
:! and/or cotter in Ref 13, of Japanese bombs in Refs 6 & 12 and
*
. . .. .
,,, . pins are replac- of some Russian bombs in Ref 4a
y? \
PARACHUTE
. . ,,,\ ii , Following is a brief description of US types of
\.
\;
I e d by an arming
.(
wire which is bombs
S-WLWWD FIN .:. ,,\
A) Bombs, Explosive or High Explosive(HE). These

Js?ikz;; Methods of Stabilizing

Bomb Flights means of suspen
sion lugs on the
are intended for the destruction
bridges, military
destructive
by projection
displacement
installations

of the case(fragmentation),
of enemy bldgs,
and the like. The
effect is produced by deton(blast

of earth and structure s(mining or

heaving effect). They may be subdivided
~d by

into:
effect),

side of the body. a) General Purpose (formerly ca Ued demolition) .

 B 228

These bombs are used for the majority of bombing s crete construction
“’” ‘-*-Y .
operations and can produce blast, fragmentation or ‘“ The case of SAP
mining effects. . .... .//.- bombs is inter-
r
Theyrange in size - -:c’a mediate in thick-
Semi-Arm-or-Piercing
from 100 to 12001b (100&1b) ness betw that of
and their chge (Tri- AP & GP bombs. The percentage of HE(usuaHy
tonal, Comp B, Picratol) is ca 30% of the total wt. The bomb is
TNT or Amatol) provided with a delay type tail fuze. The total wt
General Purpose (1000-lb) averages ca >0% of is from 500 to2000 lb(Refs 7,9 & 15) (See Fig)
the tot~ wt. The e) Depth (D) (called by Hayes antr’.subrnarine). They
bomb body is cylindrical, has an ogival nose and are light-case bombs designed primarily for use
tapers conically to the base. The bombs are gen- against submarines.
erallv fin-stabilized and nose and tail fuzes are The case is cylin-
- .-—.*.-_.&
used’in most of them(Refs 7.9 & 15) (See Fig) drical in shap~ ard
b) .Ligh t Ca.se(L C). These and some demolition bombs { has a flat nose to
*C reduce or prevent
are designed to carry a heavy chge of expl (70% or
more of the total 1., .—
.+.___ ricochet when drop-
wt) to produce the Depth Bomb(650-lb) ped from planes fly-
... ...---* -’ %-. .
./- max blast effect. ing at low altitudes.
T y are similar They are usually loaded with HBX, HBX-1 or” TNT
N iii shape to GP (70% of the total wt of the bomb) and provided with
‘.- -.-..—— .= bombs, but the a hydrostatic tail fuze that functions at a predeter-
Light Cose (4000-lb) case is lighter mined depth. A nose fuze that functions with instan-
anrL thinner. They taneous action on impact may be used to produce
are equipped with proximity, instantaneous & non a surface burst, when the bomb is used against a
-deIay fuzes to provide above ground bursts. Their surface target(Refs 7,9 & 15) (See Fig)
total wt is usually betw 4000 & 10000 lb, but there f) Fmzgmerztation(F). They are designed for high
are also heavier types. The so-c ailed blockbusters -velocity projection of fragments from a s qu are
(qv) are very heavy LC bombs(Refs 7,9 & 15) (See steel bar that is wound helically around the bomb,
Fig) to inflict damage to personnel and light materiel.
Note: Brit designation LC meams “light case chem- Their HE chge(usually Comp B or TNT) average
ical bombs” only 14% of the total wt, which ranges from 4 to
c) Armor- Piera”ng(AP) and Armor-Piercing Capped 260 lb. They are fin- or parachute-stabilized(See
(APC). AP bombs are used to pierce highly-resist- Figs), except the small(4-lb) bomb, which is
?_ targets, such as stabilized with “butterfly wings” (See below under

.
.<f—~’
A ....
..-— “=!E3 ‘“. - “ —.

Armor- Piercing-”
_-
.L
.. concrete bomb-
proof construction
and the heavy
List of Bombs). All small
may be assembled
airplane as a unit(Refs
in
—
clusters
and medium size bombs
and dropped from an
7,9 & 15)

em
(1000-Ib) deck armor of bat-
tle ships. The case is very thick at the nose and
the wt of HE, sufficiently insensitive to withstand
the force of im-

xl
~<- >>.1”
pact(such as Expl
x 3 .:=- “Fin Type
~d. ~ D), is only ca 15%
Copped Armor-P iercing
of the total wt.
(100&1b) The bomb is pro-
vided with a delay-type tail fuze to permit deep
penetration of the target before deton. The wt of
*
these bombs is betw 10~0 & 1600 Ib(Refs 7,9 &
15) Some sizes also have a cap on the nose and
they are designated APC(Ref 9,p 232)(See Figs)
d) Semi-Armor- Piercing(SAP). These are used
against Iightly armored ships and reinforced con- Frogmentotion Bomb,
parochute Type

.
 229

B) Bombs, These may be subdivided

Chemical. graphy. The charge is either photographic flash
into gas, smoke and incendiary powder(45% of total wt of the bomb) or metal-alloy
a) Gas. These bombs are filled with a chemical dust(75% of total wt). The bombs are usually fin
warfare agent(CWA) intended to produce on bursting -stabilized and provided with mech time fuzes to
of the bomb some physiological effects, including produce air bursts(Refs 7,9 & 15)
lung irritants, vesicants, Iachrymators, irritant b) Target Iderzti/ication (77). There are two kinds
smokes and nerve and blood poisons(Refs 7,9 & of TI bombs, both of which are fin-stabilized and
15) (See also Chemical Warfare Agents) provided with mech time nose fuzes to produce
b) Smoke. These bombs are filled with a chemical air burst. The ground-marker bomb contains pyro-
[such as titanium tetrachloride(FM), hexaehloro- technic candles and is used to locate, illuminate
ethane-zinc mixt(HC), chlorosulfonic acid-sulfur and mark targets at night. The candIes are ignited
and ejected from the bomb tail and they continue
trioxide soln(FS), white phosphorus or plasti-
cized white phosph,oru s(PWP)] which produces on to burn while falling to the ground. The red-smoke
bucsting of the bomb a dense smoke intended to bomb is used to indicate a bomb release point
screen the movements of troops, ships, location of when ground targets are not discernible. The bomb
artillery etc. Bombs filled with WP or PWP may be functions in air, the burster rupturing the case and
considered as a combination of screening smoke expelling the filler(powdered hemitite, FezOa ),
and incendiary because burning particles of WP which produces a persistent red cloud(Refs 7,9 &
are scattered together with the smoke(Refs 7,9 & 15)
15) (See also under Chemical Warfare Agents) D) Bombs, Leaflet. They are 100 and 500-Ib
cylindrical bombs used to
‘?
c) lrzcerzdiary(l,). They are filled with material [such distribute literature from
8% .
as thermite, thermate(TH), powd Mg, AI or their I amcraft. The case is cut
sm!raoN alloys, incendiary oil, paraIIel to its axis into
rs4
SUS4DIAW napalm, peptized NP 1-1 two equal parts which
- !

3/”
(PTI), etc] which’scatters . separate in the air when
UUMNUM

&--
PANl and burns at extremely the fuze functions, thus
,, high temps; thus starting allowing the leaflets to
,.‘.
& intensifying fires and fall and disperse
.
4/& IAONLUUM #
Y 1! .l& AUOY harassing & causing cas- (Refs 7,9 & 15)

“tiiillk 4 j rr!MNo .6’

1AM (See Fig)
r cowmmor4 ualties. Some bombs have
NEEOK
TAND
IGNITER
WrIYm
casings
incendiary
constructed of
metals, such as
Leoflet Bombs
(500 & 100-lb)

Incendiary Bomb Mg(Refs 7,9,15 & 16) (See E) Bombs, Practice and Practice Target. Both

\
(2-lb) Figs)
. .. . . kinds are used for practice to simulate service
IL PR!MER AND 80W
f:~~= bombs. The practice bombs range from 23 to 250-lb
0“.,
,m. F,.(NG P(N HOLDER “’M” ‘OLDER
,Mn?.l,,w
.uOW
~

but there are a I so miniature bombs in 3 and 4.5-lb

~7’”+
e
F ,RST F IRE CHARGE
1 ,.-.1.-’- fuzes. Most practice bombs have a spotting charge,
,“ h9#.. ,. others are completely inert. Some bombs are made
FIR, % PIN SUPFURT - SAFETY PLUNGFR
FIRING PIN
TMERMATE
Pt.u6
of thin metal and they require sand-loading to give
Incendiary Bomb (4-lb) Dm.AY LWCNATOI’ the desired wt before use, others do not require it
because they are constructed completely of rein-
Note: All chemical bombs burst above the ground. forced concrete except for the fin assembly and
They are provided with an instantaneous fuze and spotting chge. The practice target bombs are of
a bur.ster( such as of Tetryl), which is used to rup- 100-lb size and are used to produce a colored tar-
:ure the bomb case and to release and assist in get on snow-covered ranges. These bombs are fitted
scattering the fiHer(R ef 2,P 604) with a nose fuze and a burster to scatter the hem-
C) Bombs, Pyrotechnic. They contain pyrotechnic atite (Fe ,Oa ) filler, producing a red coloration on
naterials and are classified as bombs because of the targe~ a~ea (Ref 15,pp 171-2)
:heir similarity to bombs in body, fuzi ng and F) Bombs, Dummy. Completely inert bombs and
nethod of suspension. These bombs may be sub- components used for training ground crews in
iivided into: assembling, fuzing, unfuzing and other handling
J Photoflash. These are thin-cased bombs design- details of bombs. Each type and wt of service
:d to burst in the air and to produce a light of bomb is represented by a corresponding dummy
ligh intensity and short duration for night photo- bomb. Dummy bombs are constructed from the
 B 230

metal parts of service bombs, inert-loaded when

necessary. Dummy bombs, unlike practice bombs,
are not expendable, nor are they dropped for
bombing practice(Ref 15,p 172)
Bombs may also be classified as listed in
KET
Ohart(Ref 7,p 221): a)according to service use
as service, practice & drill b)according to
tactical use as GP, fragmentation, AP, SAP,
chemical, light case 6 dep!b c)according to the
actual fil Ier as high-explosive, practice (filled
with a spotting chge), chemical & miscellaneous
(filled with some special filler for a particular
purpose) and d)according to capacity or the
percentage of the filler wt to the total wt, as
low-capacity, medium-capacity and biglmcapacity
The center section was the demolition part fiIled
Oh art further defines: a)service bombs as for
with HE an d equipped with a delayed-action fuze
use against the enemy to dodamage to matfriel
that acted onIy after the bomb penetrated the
and personnel, regardless of the filler b)practice
target. The nose section contained about a dozen
bombs as for training of aircraft crews, especially
smalI incendiary bombs which were released by a
bombardiers, the bombs have the same flight char-
timing device at the desired moment. The incen-
acteristics as service bombs but usually are load-
diary bombs scattered burning material setting
ed with a spottin g charge to give indication of
numerous intense fires, thus completing the de-
burst c HrilI bombs as to train ground crews in
struction caused by HE
assembling, fuzing, unfuzing and other handling of
Some aerial bombs of WWII. were equipped with
bombs; these are totally inert and are not expend-
rockets to give them added velocity and penetra-
able d) low. capacity bombs as less than
ting power after being launched from an aircraft
50% (percentage of filler wt to total wt), such as
The foreign bombs of WWH are described in the
AP for which the capacity is 5-15%, SAP ca 30%
following Department of the Army Manuals: TM
and fragmentation ca 30% e)medium-capacity (MC)
9.1985* l(Conf)(Ref 10)-British; TM 9~198&2(Ref
bombs as ca 50%, such as GP bombs and f)bigb
11)-Germ an; TM 9. 198&4(Ref 12)-Japanese; TM 9
-capacity(HC) bomb. The definition of the latter
l 1985.6(Ref 13)-French & Italian. The German
is given separately under Bomb, High Capacity
bombs are also described in Ref 16, the Japanese
(qv). Ohart also lists a glide bomb(Ref 7,p 202)
in Ref 6 and some Russian bombs in Ref 3a
and a shaped-charge bomb(Ref 7,p 240). The
glide bomb is fitted with wings and other control Re/s: l)Marshall 2(1917),564 2)Hayes(1938),
equipment and released from a plane at high s98-616 3)WilIy Ley,’fBombs and Bombing”,
altitude. It then glides into the target at a fixed Modern Age Books,NY(1941) 3a)G.Dyakov,
glide angle, say 10”, and is released at a safe Khimiya i Industriya 19,285-93(194 l)(Incendiary
distance from the target. If released at an altitude & HE bombs) 4) J. R. Newman,’’The Tools of War”,
of 20000ft, the bomb would travel ca 20 miles Doubleday,Doran & C0,NY(1943),270-90 & 357-63
before impact 4a)US Bomb Disposal School, ‘United States
Hayes(Ref 2,p 605) and TM 9-1980(Ref 9,p 55) Bombs and Fuzes”, Navy Yard, Washington,DC
classify the inert bombs as practice, drill and (1943) 5)Anon, “Ammunition Inspection Guide”,
gage. The use of practice bombs is for the same War Dept Manual,TM 9. i904(1944),548-708
purpose as the practice bomb described in TM 6) Anon, “Handbook of Japanese Explosive Ordnance”,
9-1900(Ref ls,p 171), while the use of the drill OPNAV 3O*3M(1945),66-1O7 7)Ohart(1946)195 -217
bomb is the same as that of the dummy bomb of 8)All&EnExpls( 1946), 164-9(Bomb high-explosive
Ref 15,p 172, The gage bomb serves for gaging trains) 8a) J. M. King, “Bombs ”, Lecture delivered at
and testing new types of airplanes for clearance, PicArsn,Dover,NJ on 27 February,1948 9)Anon,
capacity and functioning of bomb racks. Such “Bombs for Aircraft”, Dept of the Army Tech h4anual
bombs are not issued to the field services TM 9*1980(1950), 1-59 10) Anon, “British Explosive
Ordnance” ,Dept of the Army Tech Manual TM 9
Newman(Ref 4,p 362) describes briefly the so l 1985* l(1953)(Conf), 1-158 & 178-204 ll)Anon,
-called breadbasket bomb made in two sections. “German Explosive Ordnance” ,Thi 9.19852( 1953),

r——— ———
 B 231

1 to 123 12)Anon, ”Japanese Explosive Ordnance”, (Bomb,gas, 1000-lb, AN-N79; AC or CG loading as-
TM9*198&4(1953),l to 121 13)Arion, ”Italian and sembly); MIL-B-14322A(Bomb, gas,10-lb,M125Al);
French Explosive Ordnance”,TM 9s19854(1953), MIL-B-14440 & MIL-B-14322(Bomb, gas, persistent,
lto 27& 177to 188 14)ArmamentEngrg( 1954), GB,10-lb,M125Al); hIIL-B-11932 & MIL-B-12654
315-30(Aerial bombs) 14a)G.McAllister, Ed, ”The (Bomb, gas,persistent, HD,115-lb,M70Al ;components
Bomb: Challenge and Answer” ,Batsford,London & Ioading assembly,); MIL-B-12383 & MIL-B-12860A
(1955 ) 15 )Anon, “Ammunition, General” ,Dept of (Bomb,gas,persistent,HD,125-lb,Ml13; components
the Army Tech Manual TM 9-1900 (1956),60-7 & 156 & loading assembly); MIL-B-10514A(Bomb, incendiary
-72 15a)Federal Civil Defense Administration, 4-lb, AN-M50A3; components for); MIL-B-11392B
“Radiation Physics and Bomb Phenomenology”, (Bombs, incendiary,4-lb, AN-M50 types); ML-B-1OO84
USGPO,Washington, DC(1956) 16)PATR25 10(1958] & MIL-B-1 187 lA(Bomb,incendiary, PTI, 10-lb,M74);
Ger 14 to Ger 20 17)Ordnance Ammunition Center, MIL-B- 13393 & MIL-B-13393A(Bomb, incendiary
“Ammunition Complete Round Charts” ,Book III, 100-lb, AN-M47A4); MIL-B-14 152B((Bomb,> 00-Ib,
Joliet,Ill(1959 ), Charts 1 to 10 incl 18)US Speci- Ml 15; components and metal parts assembly); MIL
fications for Bombs: MIL-B-13686(Bomb,body); -B-12835 (Bomb,leaflet,500-lb, M105Al ,metal parts
MIL-B-14349(Bomb,4-lb, Ml14); MII--B-2O436 & for); MIL-B-2529(Bomb ,Iight case,4000-lb,M56 A2;
MIL-B-20485(Bomb, fragmentation,4-lb,M83); MIL metaI parts assembly); MIL-B-1396(Bomb, photoflash
-B-20479( Bomb, fragmentation, 30-l b,M5, metal parts AN-M46); MIL-B-11111 & MIL-B-1 1128(Bomb,photo-
for); MIL-B-12097A(Bomb, gas,500-lb,AN-h178 :com- flash, M120;metal parts for, loading, assembling &
ponents for); MIL-B-12029A(Bomb,gas, 1000-lb,AN packing); MIL-B- 12720 & MIL-B- 14226( Bomb, photo-
-hf79; components for); MIL-B-13049A(Bomb, gas, flash,Ml 22; metal parts for, loading, assembling &
hoto-

r--’l%!w f+----+ 1/ )111 rT!!![ Id L!-LJ

4 u....

A-BOMB, Depth, TNT, 350-lb, AN-Mk 54 Mod 1

B-BOMB, Gas, HD,l 15-lb,M70Al
M-Cluster,
N-BOMB,
Fragmentation
SAP, Picratol,500-lb,
if!!!
x

Bomb, M28A2(100-lb)
AN-M58A2
C-BOMB, Photoflash, 100-lb, AN-M46 (M46) O-BOMB, Incendiary,500-lb, AN-M76
D-BOMB, Smoke, PWP, 100-lb, AN-M47A4 P-BOMB, Gas, 1000-lb, AN-M79
E-BOMB, Practice, 100-lb, M38A2 Q-BOMB, SAP, Picratol,1000-lb, AN-M59A 1
F,BOMB, GP, Tritonal,2 50-lb, AN-M57A1 R-BOMB, AP,Exp D, 1000-lb, AN-Mk 33
G-BOMB, GP, TNT, 100-lb AN-M30A1 S-BOMB, AP, Exp D, 1600-lb,AN-Mk 1
H-BOMB, Fragmentation, TNT,23-lb, M72A1 T-BOMB, GP, Tritonal,2000-lb, AN-M66A2
[-BOMB, Fragmentation, TNT,20-lb, AN-M4 1A] U-BOMB, LC, TNT,4000-lb,M56A2( AN-M56A2)
J-BOMB, Incendiary, 4-lb, AN-M50A2 V-BOMB, GP, Tritonal, 12000-lb, M109 (T IO)
K-BOMB, Fragmentation, TNT, 4-lb, M83 W-BOMB, GP, Tritonal,22000-lb, Ml 10 (T14)
L-BOMB, Practice, Miniature, 3-lb, Mk23 X-BOMB, GP, Tritonal,44000-lb, T12
 1

B 232

flash, T93;metal parts for, loading, assembling & in incendiaries are described) H)H.K. Linzell,USP
packing); MIL-B-20498(Bom b,practice,17-Ib, M37, 2424937(1947) & CA 41 ,7120 (1947 )( Incend mixt
low altitude, parachute type); MIL-B-20463(Bomb, cent Al 51.1 & CaS04 48.9% is recommended as
practice, 100-lb,M38A2; metal parts assembly); filler for bombs because it develops more heat than
MIL-B- 12880 (Bomb, practice,25 O-1b,T5 2E3; metal thermite mixts) I)H.S. Beckman,0rdnance32,98-9
parts for); MIL-B-20411 [Bomb, practice target, 100 (1947) (HE bombs; method of manuf & loading)
-lb,M75A 1 and bomb, target identification, 100-lb J)Anon,Ordnance 32,364(1948)(2 I-Ton Bomb) (.4
(smoke,red),M84Al; Ioading,assembling & packing)] bomb, 4.5’ in diam, 26’10” in length and weighing
MIL.B-10492A(Bomb, practice target, 100-lb, M75Al, 42000 lb, was dropped at Muroc Air Base, Calif,
metal parts for); MIL-B-1397(Bomb, target identifica fro,n a Boeing B-29 Superfortress, for the purpose
tion,250-lbM89, M90,M91, M98 & M1OO); MIL-B-2521 of testing. While lacking the destructive power of
(Bombs, seamless, metal parts assembly); MIL-B atomic missiles, the 21-ton bomb has an advantage
-20452( Bombs ,fragmentation, 90-lb,h482; 120-lb,M86 in that it leaves no radioactivity which might deny
and 220-lb, AN-M88; metal parts for); MIL-B-20497 use of a captured area to the attacking forces)
(Bombs, fragmentation,M40Al, AN-M41Al,M72A 1; K)C.hLCawley et al, JInstPetroleum(London) 34,90
and practice M71A 1 & M73A 1; parts for); MIL-B -108(1948) & CA 42,3961 -2(1948) (Discussion on
- 10746B(Bombs ,smoke or incendiary, AN-M47A4; various incendiary mixts for bombs, mortar shells,
100-lb, PWP,WP,PTI,IM & NP; loading assembly); etc) L)H.H.Cooke et al,USP 2445311(1948) & CA
MIL-B-2501(Bombs, steeI,GP & SAP,metal-arc weld- 42,7985( 1948) (Incorporation of isoolefin polymers
ed; general spec for the construction of); MIL-B-2530 of high mol wt with flammable naphtha produces a
(Bornbs,steel,GP &SAP,resistance welded; general high-viscous mass almost semisolid in consistency
spec for the construction of) 19)A.B .Schilling, which is suitable for incendiary bombs) LI )D. p.
PicArsn; private communication 1961) O’Brien,USP 245 1864(1948) & CA 43,1190(1949)
Additional References Discussing Principally Bomb (An incendiary and demolition bomb contg Mg 2 oz,
Fillers Ca3P2 2 drams & KC104 1 dram) h4)H.H.Cooke et
A)A.Stettbacher,SS 12,227-30(1917) (Incendiary & al, USP 2445312(1948) & CA 42,7986 (1948) (An in-
HE bombs) B)G.Dyakov,Khimiya i Industriya 19, cendiary bomb contg a nose fuze, a BkPdr ignition
285-93(1941) & CA 38,2209( 1944)(Russian HE & chge, a thermite nose chge and a tube of thermite
Incendiary bombs) C)W.Guldiman,Protar 7,59-62 extending through a gummy Iiq obtained by mixing
(1941) & CA 35,5701(1941) (A brief description of naphtha with a high polymerj such as an isobutyl-
airplane bombs, such as incendiary, HE, fragmen- ene polymer, mol wt 50000 to 100000) N)K. J.
tation, gas and special bombs) D)V.Leonard, BritP Mysels,IEC 41, 1435-8(1949) & CA 43,8179-80(1949)
537010(1941) & CA 36,1496(1942) (Picryl fluoride (Discussion on Napalm-mixt of Al disoaps used in
as an expl chge for bombs) D, )R.C. Allen,LEP incendiary bombs and flame throwers ) N, )J .M.
2273166(1942) & CA 36,3964(1942) (Explosive King, “Bombs”, Lecture delivered at Picatinny
bomb contg a liquefied gas together with an ex- Arsenal,Feb, 1948, 27pp O)L .Finkelstein,USP
plosive) E) L. Feiser et al,IEC 38,768-73(1946)& 2553568)1951) & CA 45,7354 (1951 )( Gelled gaso-
CA 40, 5567(1946) (Napalm for use as a gelling or line intend compn is obtained by dissolving 3 ps of
thickening agent employed in the gelled-gasoline stearic acid in 88.75 ps of gasoline, adjusting the
fuels used as filling for incendiary bombs and in temp to 26° and stirring into a mixt of 5 ps isobutyl
flame throwers) E, )A.Grobstein,USP 2403656(1946) methacrylate, followed by 2 ps C aO and 1.25 ps
& CA 40,5568(1946) (Nitrides of Li,Ce, K,Ca or La of w. Careful addn of w gives control of the thick-
contained in a capsule may be placed in an incen- ening rate) P)J.A. Southern et al, USP 2570990
diary bomb together with thermite or other m ixt to (1951) & CA 46,1768(1952) (A solidified fuel for
produce high penetration and corrosive effect on incendiary bombs, grenades, flame throwers, etc
burning) F)E.Wetter,Protar 12,105-10 & 133-8 consists of gasoline and 7-14% by wt of a soap
(l946);cA 40,5920 & 6259(1946) (Comprehensive -type gelling agent which is composed of Al oleate
descriptive article on the history, development and 50-75 & Al stearate 50-25 to which is added ca
types of airplane bombs and their fuzes) F1)H. lp of an oxyaromatic antioxidant compd and ca 4
Graham,et al, CanChemProcessInds 30,N0 11,37-41 -10 ps of Na oleate soap contg some Na stearate)
(1946) & CA 42,4753( 1948)[Bomb filling with 80/20 Q)D.E.Floyd,USP 2662068(1954) & CA 48,4222
amatol(AN 80 & TNT 20%) is discussed] G)R.W. ( 1954) (Polyamides, such as one prepd from 1 mol
Hufford,ChemEngrg 53,N0 10, 110-13(1946) & CA of cetylmalonic ester and 1 mol of l,3-diamino-
41 ,286( 1947) (Chemical Warfare Service developments propane, me suitable gelling agents for gasoline,
 B 233

octyl ale, cyclohexane, cyclohexanol, etc; the gels vailing winds so that sparks will not be blown to-
thus obtained are recommended for incendiary bombs ward the location of expls, ammo, etc. Where pos-
and for flame throwers) R)M.D. Banus & J.J ,Mc- sible, natural barricades should be utilized betw
Sharry,USP 2688575(1954)& CA 43,14210(1954) the site and operating bldgs and magazines. When
(Prepn of fast-burning Ti or Zr powders for use in destroying bombs, expls or ammo by burning, the
first-fire mixts for incendiary bombs or shells is possibility that the mass may detonate must be
described) S)L.Cohen,USP 2718462 & 2741629 recognized and appropriate barriers or distance
(1956); CA 4916271(1955)& 50,11693 (1956) (Al separation utilized for the protection of personnel
soaps of isooctoic acid as gelling agents for Iiq and property
hydrocarbons, the gels thus obtained are useful in The area around the place of destruction must be
incendiary bombs and in flame throwers) T)H. A. cleared of dry brush, grass, leaves and other com-
Richards et al,USP 2741 177(1956) & CA 50,10412 bustible materials for a radius of 200 ft. The de-
( 1956) (The construction of an incendiary bomb for struction grounds should be of well-packed earth
ejection of gelled on thickened fuels is described) which is free from Iarge stones and deep cracks in
U)R.E.Van Strien et al, USP 2751283, 2751284, which expl items might lodge. ExpI materials shall
2751359, 2751360 & 2751361(1956); CA 50,13483 not be burned or detonated on concrete mats
(1956) (Al soap gelling agents for Iiq hydrocarbons Fire-fighting facilities should be readily avail-
used in incendiary bombs, grenades, & flame able to extinguish brush or grass fires and, if
throwers are discussed) V)L .D.Jackson,USP necessary, to wet down the ground betw burnings
2796339(1957) & CA 51,13399-13400( 1957)(A mixt and at the close of each day’s operation
of Sr nitrate 60-90 & boron 40-10% produces a flame Material awaiting destruction should be stored
of great brilliancy & high temp and will burn under at not less than the min dist from adjacent tempo-
w; it is suitable for use in incendiary bombs or in rary stores of expl materials and from bombs being
flares) W)J.C.Loftin et al,USP 2824515(1958) & destroyed, as required in Ref 2, Section 17 or in
CA 52,8560( 1958) (An incendiary bomb, which in- Ref 3,p 66-70. The material” should be protected
corporates Cd in its casing or in the fiIler, pro- against accidental ignition or expln from fragments,
duces a toxic CdO aerosol on burning) X)C.B. grass fires, burning embers or detonating impulse
Linn,USP 2881060(1959)& CA 53,14522(1959) originating in materials being destroyed. A bomb-
(Some products obtained on condensation of hydro- proof shelter or a barricade of sufficient strength
carbons with carbohydrates are suitable as geHing to provide protection for personneI should be
agents for fiquids such as benzene, toluene, etc. erected at a dist of not less than 300ft from the
The gels thus obtained are suitable as incendiary destruction area
fuels for bombs) Y)R.E.Sckad,USP 2891852(1959) Bombs intended for destruction are usually transp-
& CA 53,17515( 1959) (Materials suitable for filling orted in special trucks, marked “Explosives” and
bombs, grenades, etc are obtained by mixing nitro- “Danger”, with no more than two persons riding in
hydrocarbons, such as nitro- & dinitromethane, etc the cab. As soon as all items have been removed,
with devinylated ketoses or diaryl deoxyketitols, trucks shouId be withdrawn to a safe location until
prepd by reaction of C3-8 ketose sugars with CG.24 destruction is complete. No more than 100lb of
aromatic hydrocarbons) Z)E.E .Bauer & G. Broughton, bombs or other expl items are allowed to be de-
USP 2922703(1960)&CA 54,7149-50(1960) [A stroyed at one time. The destruction of bombs
thickened, stabilized incendiary fuel(having con- 1arger than 100lb should not be undertaken in the
trolled consistency and which will not flake or US w/o approval of the Chief of Ordnance
scale) is prepd by adding to the hydrocarbon-soap Destruction of bombs may be done either by
mixt a silica gel which contains not over 5.5% w burning or by detonation
and passes at least a 28-mesh screen] a)Burning. Bombs and their components(such as
fuzes, adapter boosters & primer detonators) may
Bombs, Destruction of. Ths site used for the de- be destroyed by burning. For this, the materials to
struction of bombs, ammo or expls should be locat- be burned are placed in a pile and, after covering
ed at the max practicable distance available from the pile with combustible s(such as wood, rags,
all magazines, inhabited bldgs, public highways, paper, etc), some oil is poured over it. The ig-
railways and operating bldgs. The separation nition may be achieved either with a train of com-
should not be less than 2400 ft unless pits or bustible material or with t~ aid of safety fuse of
similar aids are used to limit the range of fragments. length sufficient to permit personnel to reach the
Sites must also be located in relation to the pre- protection of a shelter. The pile may also be ig-
 I

B 234

nited with BkPdr s quibs initiated by an electric in factories and in other ways. It is, necessary,
current controlled from a safe distance. It may therefore, to dispose of any unexploded bombs as
be necessary to tie in two or more s quibs to soon as possible. This is a very difficult and
assure ignition of the combustible train. Ignition dangerous task because there exists a great variety
of a stock-pile of bombs is often followed by of fuzes, many of which are equipped with anti-
detonation withdrawal devices. Only trained personneI must
In cases of misfires, the persomel shall not be used for bomb disposal. For this reason special
return to the place of destruction for at least 30 Bomb Disposal Schools were established in various
reins countries before and during WWII, most of which
When burning is completed, the ground must be are still in existence. One of these schools is
thoroughly soaked with w if burning of the next located at PicArsn,Dover,NJ
batch is done within 24 hrs. If it is expected that As it is impossible to give a brief instruction on
toxic gases will be evolved on burning, personnel bomb disposal, it is advisable to consult one of the
must wear gas masks or other protective de- special manuals, such as the British, ‘Bomb Dis-
vices posal Manual”(listed in Ref 7) or US manuaIs and
b)De tonation. Stock piles of bombs may be desrroy- pamplets listed below as Refs 3,4,5 & 6
ed at the site by first removing the nose or tail Re/s: l)R.L.Piech, ‘Bomb Disposal”, Ordnance
plugs of bombs at(regular intervaIs in the pile) and Sergeant,Bomb Disposal School, APG,Md(Aug 1943)
inserting either chges of plastic expls or cut-down pp 108-15(A brief discussion of bomb disposal
ZIb blocks of TNT in the empty fuze cavities. The during WWII) 2)US Bomb Disposal School, Potomac
chges should be primed for simultaneous deton and River Navy Yard, “United States Bombs and Fuzes”,
provisoin should be made for dual ignition by fitting Washing~on,DC(1943) 3)Anon, “Shaped Charge Am-
at least two chges with blasting caps and sufficient munition and Applications of Shaped Charges to
length of safety fuse to permit all men to take safe Explosive Filled Ordnance” ,US Navy Dept,Bureau
cover of ordnance Publication OP 1720(1947), 18-31
Explosive-contg bomb components may be deton~ (Opening of explosive-filled bombs by firing small
ted w/o being unpacked by placing z or l-lb blocks shaped charges into midsections of the bombs)
of TNT in packing boxes in the amt of l-lb blocks 4)Anon, “Explosive Ordnance Reconnaissance and
per each 100-lb(gross wt) of components. The Disposal” ,Dept of the Army Field Manual,,
chges of expls should be distributed throughout 9-40(1953) 5 )Anon, “Ordnance Service in the
the pile and primed for simultaneous deton and Field”, FM 9-1 (1959) 6)Anon, “Ordnance
dual ignition as described above for bombs. If Ammunition Service”, FM 9.5(1959) 7)A.B.Hartley,
chges are primed with a safety fuse, personnel “Unexploded Bomb, A History of Bomb Disposal”,
should take cover after the fuse is ignited, and Norton & C0,NY(1959)(A detailed description of
if electrical ignition is used, personnel should bomb disposal conducted in GtBritian during and
take cover before the circuit is cIosed after WWII) 8)Office, Chief of Ordnance”, Program
Note: When practicable, the st akcs of bombs for Neutralization and Disposal of Explosive
should be covered prior to detonation with earth Material”, Technical Information Repott G,TIR G,
in order to reduce the effective range of missiles Washington,DC( 1960(Conf)(Not used as a source
and to assure high-order deton of info)
Re/s: I)Anon, ‘Bombs for Aircraft”,TM 9~1980
(1950),28 1-2 2)Anon, “Ordnance Safety Manual”, Bombs, Incendiary, Extinguishing of. Bombs of the
ORDM 7.224( 1951),27-7 to 27-15 and Secrion 17 incendiary type were introduced during WWI but
3)Anon,”’Care, Handling, Preservation and De- they were not effective and were comparatively
struction of Ammunition”,TM 9*1903 (1956),66-7 easy to extinguish. In fact, some fires caused by
& 169-83 4)F.C.Ikl; , ‘The Social Impact of explosive bombs striking near flammable materials
Bomb Destruction”, Univ of Oklahoma Press, were more cliff icult to extinguish because the
Norman, 0kla(1958)
destruction and dfbris which were wrought by the
expln made it practically impossible for fire
Bombs, Disposal of. An unexploded enemy bomb
fighters to reach the sear of the fire. As explosive
represents great danger because the time of its bombs are heavier, not as many can be carried by
expln is unknown, and if it explodes there could be a plane as incendiary bombs
real damage to life and property in residential Incendiary bombs of WWI were of two types:
are as, and interference with industrial production a) ’Therrnite that consisted of a steel shell filled
 B 235

with a mixt of iron oxide and powdered Al. Upon bomb used during WWI, however, this thermite serv-
ignition of this chge the following reaction takes ed only to ignite the Mg shelI and not as the main
place: 8A1 + 3Fe904~ 4A120$ + 9Fe, libera- incendiary material. The thermite reaction within
ting a large amt of heat(temp 2500 C = 4532° F ). the shell was initiated by an igniter in either the
As soon as the steel shell is penetrated by the nose or tail of the shell. The igniter consisted of
heat, the reaction is nearly completed b)Liguid a small percussion cap into which a needle was
/uel bomb that consisted of a steel shell filled driven when the bomb impacted. Unlike other
with I to IOkg of gasoline or other highly flammable types of bombs an electron bomb did not explode
liquid. Upon impact, this liquid was ignited, but upon impact but started to burn on the inside. The
with such small amts of incendiary liq the result- violent reaction of thermite, developing a temp of
ing fire would tend to burn out before penetrating ca 2500°(45320F), caused jets of fIame to be
and setting fire to the immediate surroundings. emitted from vent holes in the shell together with
Only when the bomb struck very near some readily bits of molten Mg. These particles caught fire in
combustible material was there any danger(Ref 1) the air and scattered in every direction for a dis-
The incendiary bombs of WWII were much more tance of ca 50ft. The scattering continued as long
effective as also were the bombing planes. This as the thermite reaction preceded (ca 1 rein). By
made it possible to conduct incendiary bombing this time the pressure in the bomb had decreased
on a very large scale, especially by the Americans and the Mg shell became ignited. The shell then
and British. For instance, accdg to Stettbacher burned for 1O-15 min at a temp of ca 1300°(23720F]
(Ref 16), the number of incendiary bombs dropped setting fire to any combustible material within a
on Koln(June 28, 1943) was 100,000, on Berlin radius of several feet
(March 8,1944) 200,000, Tokyo(March 15, 1945) Electron bombs were usually dropped from a
325,000 and Hitler’s Headquarters(May 25,1945) height of a mile or more in lots of ten or twenty.
600,000. Damages and casualties inflicted by A singIe plane could carry 1000-2000 of such bombs.
incendiary bombs were about ten times greater An electron bomb dropped from a height of ca 1
than that caused by explosive bombs(Ref 16) mile would usually penetrate an ordinary wooden
Many types of incendiary bombs were developed roof deck or covering material and start a fire in
during WWII of which perhaps one of the most effec- the top story or attic of a bldg. If not quickly ex-
tive was the “Elektron Bombe” (electron bomb), in- tinguished the bomb would burn through the floors
vented by the Germans. It was made in sizes from and set fires everywhere in the bldg
1 to 25kg. The most common, l-kg bomb, is repre- The electron bomb can be extinguished in any
sented here. It consisted of a thick-wailed Mg-Al one of several ways, ttie idea being, of course,
alloy shell ca 9“ in length and. 2“ in diam, weigh- to extinguish it or bring it under control before it
ing ca 0.8kg and was filled with a small amt of has caused a major fire. While the thermite reaction
t ~ermite mixt. Unlike the thermite-type incendiary is in progress the bomb cannot be smothered be-

—. . -—
—= . -. 0
L—

Air Raid PrecaucLm Handbook No 9, British Government

Drawing and cross-sectional view of a typical one-kilwvam, Electron bomb.
Note blunt nose and awkward streamlining. With the exception of the sheet iron
tail and firing mechanis~ the bomb is constructed entirely Of incendiary materials
 B 236

cause the oxygen entering the reaction comes from Ref 13,P 7)
the iron oxide in the mixt and not from the atmos- Of the various types of fire extinguishers only
phere. When the thermite reaction has been com- those of the water-solution type would be effective
pleted, however, and the Mg-Al shell is burning, against the electron bomb, and usually more than
the bomb is dependent upon the atm for oxygen and one extinguisher would be required. The soln
can be smothered. Although water accelerates the should be played upon the bomb in the same way
burning of Mg(this acceleration can reduce the as water from a nozzle. A /earn extinguisher might
burning time from IO- 15 reins to 2-3 reins) it can also be used but under no circumstances should a
be used to combat the bomb if applied as described carbon tetracbloride extinguisher be used. It is not
below only ineffective but it may cause dangerous gas
The reaction betw hot Mg and water is: Mg + 2H20 to be generated(Ref l,p 118; Ref 6,p 39; Ref 13,p
+ Mg(OH)2 + H2 and between Al and water: 2AI + 7 & Ref 15)
3HZ0 +A1203 + 3H2. The hydrogen ignites and will Still another device used to extinguish a small
burn without real damage so long as water is applied incendiary bomb was a snuffer. It consisted of a
sparingly. However, if water is put on too fast, the large cup(dome) about l~tit in diam, made of a wire
hydrogen may accumulate faster than it can burn mesh sprayed inside and outside with asbestos
and will explode violently. To prevent the expln of fiber. The cup was attached in an inverted position
hydrogen and to keep the bomb under control at the to the end of a long rod and when placed over the
same time, a method using a jet surrounded by a burning bomb, smothered it(Ref l,p 118 & Ref 4,
spray of water was found by the British authorities p 6)
to be most satisfactory. To fight fire by this method In Ref ll,p 5, a Russian method for extinguishing
at Ie ast two persons and speciaI equipment are re- smaIl eIectron and some other bombs is described.
quired. The equipment consists of a bucket, a dou- It consisted of “dunking” the burning bomb in a
ble-action hand pump, 30ft of hose and a special large container(such as a barrel) full of cold water.
one-eighth-inch nozzle. The 1st man pumps 80 It was claimed that this method is very effective
strokes a min to keep a pressure strong enough because here the Mg-Al alloy is chilled below its
to throw a jet 30 ft and a spray 15 ft wide. .The 2nd mp so suddenly that it stops burning almost imme-
man, in a prone position(protecting himself from diately. There should be, however, sufficient water
bits of burning Mg), hoIds the nozzle and directs to completely immerse the bomb, otherwise the
the jet into the seat of the fire and not indiscrimina- burning will proceed even more vigorously than
tely into the smoke and flame. The spray serves to without water(Ref I l,p 5)
wet down the are a surrounding the bomb and thus The methods described above we applicable
prevents the spreading of fire. The delivery from only in case of small( 1-2-kg) bombs, the heavier
the system should not be more than 1 3/4 gallons type bombs require experienced firemen for ex-
a minute. Water should never be poured onto an tinguishing fires(Ref l,p 120)
electron bomb from a pail or bucket(Ref l,p 116; Another type of bomb used to a considerable ex-
Ref 4,p 7; Ref 6,p 7; Ref 7,p 37; Ref ll,p 5 & tent during WWII was the multiple effect bomb. It
Ref 13,p 7) contained either magnesium or phosphorus in sep-
Electron bomb fires can also be brought under arate units. These units were ejected from the
control by using dry sand or other granular materi- bomb upon impact and ignition and scattered over
als, such as slag, pumice, ash, kaolin, finely di- a wide area. The burning Mg units could be handled
vided iron, graphite, etc. In this country, we have in the same m saner as the electron bomb. The P
been using speciaI coml powders, such as Gt & units couId be treated with water, but shoufd be
others. Their compositions are unknown to us. The removed to a safe place before alIowing them to
granular material should be dumped over the bomb dty(Ref l,p 120)
(completely covering it) from a long-handled scoop A new type of bomb was developed by the
,shovel and when the heat and glare of the bomb Germans in 1942. It was an incendiary bomb which
have subsided sufficiently, the bomb should be contained a fairly large chge of explosive. When it
scooped up, together with its covering, with the landed, the bomb burned for several minutes(up to
same shovel and pIaced in a metallic container 7 reins) and then suddenIy expIoded, scattering
partly filled with sand for transporting it from the the fragments in a manner similar to antipersonnel
bldg. Once the bomb has been removed, any bombs. The idea was to keep fire fighters at a
resulting fires can be extinguished by ordinary respectable distance while the fire gained headway
methods(Ref l,pp 117-18; Ref 7,P 38; Ref 12,P 5 & before expln. The bomb could not be extinguished
 B 237

by acy of the methods requiring approach.to the Explosive Charge to Keep Fire Crews out of Range
bomb, such as sand, powders of “snuffer” methods. Until Fire Has Spread”, Ibid(Dec 1942),6-7 15)S.J.
The method recommended by the NFPA to fight Pearce et al, USBurMinesReptInvestigations RI
a burning bomb before it explodes is to throw a 3686( 1943) & CA 37,2578-9( 1943) (Application of
strong jet of water from a safe distance whi~e stand- carbon-tetrachloride-type fire extinguisher should
ing behind some suitable cover, such as a wall not be used to extinguish burning Mg or thermite
or barricade. Lath and plaster walls, wooden doors, -Mg incendiary bombs, but its use on other fires
tables or chairs do not offer full protection from an should not be discoura~d) 15a)H.Bond,Edit, ‘Fire
expln. If a good cover is not avaiIable, personal and the Air War’, NFPA,Boston,Mass( 1940
risk can be greatly reduced by assuming a crouch- 16)Stettbacher( 1948),129 17)PATR 2510( 1958)p
ing or prone position. Care should be exercised to Ger 17 & 19(German incendiary bombs) 17a)R.T.
expose no more than one hand while playing a McCutchan,USP 2888072(1959) & CA 53,10765
stream of water on the area surrounding unexploded (1959) (Soln of H3B03 in glycols for extinguishing
bombs(Ref 14,P ,7) burning Mg,etc) 17b)Anon,C&EN 39, 63(Oct 23,
In the pamphlet “Fire Fighting for Householders? 1961) (Multipurpose extinguishing agent of Ansul
PA-B-4, issued by the Office of Civil and Defense ChemCo, Marinette,Wis) 18)Chester I. Babcock,
Mobilization, USGovtPtgOff, Washington,DC( 1958), National Fire Protection Association,60 Battery-
several methods for fighting fires caused by various march St, Boston 10, Mass; private communication
bombs, including A- and H-bombs, are briefly de-
scribed Bombs, Packing, Storage, Handling, Safety Pre-
Refs: l) J. A. West, Jr, ‘Total Fire-The Incendiary cautions, Maintenance, Inspection, Surveillance,
Bomb”, Quarterly of the National Fire Protection Shipping and Transportation of.
Association(NFPA), Boston,Mass(Oct 1940), 102-24 AH bombs, except the very largest, are packed in
2)H.S.Hirst & A. B. Guise, l Magnesium and Its Alloys” ~ wooden boxes or crates. The fin assemblies for
Ibid(Oct 1940), 125-35 3)A.B.Guise, “Chemical Ex- the larger bombs are also crated when packed sep-
tinguishers for Incendiary Bombs” ,Ibid(Oct 1940), arately from the bombs. Some bombs are packed
137-8 4) Anon, “Incendiary Bombs. What the British with fuzes inserted but with primer-detonators re-
Fire Fighters Learned About Them” ,Volunteer moved. However, the fuzes are usuaIly removed and
Firemen,NFPA,Boston, Mass(Nov 1940),6-9 5)W.J. packed in se sled moisture-proof cent ainers. In the
Scott, “Handling Explosives and Incendiary Bomb latter case the fuze wells in the bombs must be
Fires”, Ibid(Feb 1941),6-7 6) A. B. Guise, ‘Incen- closed with plugs. Some fuzes are packed in the
diary Bomb Fires” ,Ibid(Sept 1941),6-7 7)Anon, same containers with the bombs, others separately.
g‘A Handbook for Air Raid Wardens” ,US Office of Bombs and components are stored as shipped. Com-
Civilian Defense, USGovtPtgOff,Washington,DC plete rounds should not be assembled in advance
( 1941),36-9 8)G.Durston et al, USP 2232695 of requirements and assembled rounds should be
(1941) & CA 35,3818( 1941)(A mixt of powdered carried with sealing wires and safety in place at
fusible solid org subst, such as bitumen, with all times until installation in the plane. The arming
a inorg subst such as slate powd for extinguishing wire should remain in place until the bomb is re-
ignited incendiary bombs) 9)J? .A. Barre au, BritP leased, or until the safety pins and sealing wire
533470(1941) & CA 36,1182(1942) (A powd dealing are replaced and secured
with incendiary bombs consists of borax, carbonate Bombs and components should be stored in an
or bicarbonate of an alk earth metal, fire clay & area set aside for this purpose. Such an area should
alum) 10) W. O. Petzold,BritP 545 514( 1942) & CA be located at greater than missile distance from
37, 1606( 1943) (Sawdust impregnated with chlorides artillery ammo storage and removed from operating
of Ca, Zn & NH4, to which a little Na borate is are as, inhabited areas and public highways &
added, can be used to combat incendiary bombs, railways. These distances are given in Quantity
oil bombs or other fires) 1 I)Anon, ‘Fire From the -Distance Table for classes 9 & 10, in Ref 5,pp 66
Air, Volunteer Firemen, NFPA,Boston,Mass( July -7 and in Sect 7, Ref 7. The magazines must be
1942),4-5 12)Anon, ‘Chicago Fire Department fireproof
Teaches Simple Way to Fight Fire Bombs” ,Ibid In storing bombs, the following conditions must
(August 1942), 5 13) Anon, “Cincinnati Teaches be fulfilleck
Citizens to Control Fires from Bombs’ ,Ibid(Sept a)It is preferable to store only one type of bomb
1942),7 14)Anon, “Beware of Explosive Incen- in a magazine or igloo at one time. However, when
diaries. New German Fire Bombs Pack a Deadly conditions do not permit individual storing of bombs
 1

B 238

by type, bombs filled with Amatol, Expl D, Picratol Dangerous Articles by Freight”, established by
or TNT may be stored together. Tritonal, Torpex ICC(Interstate Commerce Commission) (Freight
and HBX-loaded bombs may also be stored together Tariff No 8). These regulations are given in Sect
b)GP, AP, SAP, LC, or depth bombs should not be ll,Ref 7
stored with any other type of ammo or expls Refs: I)Anon, ‘Safety and Storage Manual for Ex-
c)Photoflash bombs should not be stored with any plosives and Ammunition” ,00 Form N05994,uS
other type of ammo, but when the total amt of expls Army Chief of Ordnance,Washington,DC( 1928),
is less than 1000 lbs, the bombs may be stored with Sect XI 2)Anon, “Ammunition Inspection Guide”,
small arms ammo TM 9-1904(1944),552-708 3)Anon, “Bombs for
d) Fuzes or primer-detonators should be stored in Aircraft”, TM 9*19 10(1950),55-59 4)Anon, ”Ord-
a separate magazine nance Safety Manual” ,ORDM 7*224( 195 1),20-7
e)Bombs should be stored on steel or iron dunnage. 5 )Anon,”’Care, Handling, Preservation and De-
For stora~ in other than igloo or corbetta-t ype struction of Ammunition” ,TM 9~ 1903(1956),66-7,
magazines, steel dunnage should be electrically 86-7 & 147 6)Anon, “Ammunition General” ,TM
connected and grounded 901900(1956), 160 & 183 7)Sax(1957),Sections
Extreme safe ty precautions must be exercized 7&ll
in handling bombs(especially GP & LC bombs) and
protecting them from shock or heat. Containers List of Bombs
should not be tumbled, dragged, thrown, dropped
on each other or rolled on the floor. Bombs e quipped Bombs, Aerial or Aircraft. See under BOMBS
with shipping bands may be rolled if care is exer-
cized Bombs, Aircraft Depth Charge(DC). Designation
Maintenance of bombs(maintaining them in serv- of a British bomb used during WWII
iceable condition for immediate use) includes de-
rusting, repainting and removal of exudate from Bombs, AN.M.69. See VO1 I,p A457-R
the bombs and the floor of magazines. Removal
of exudate from the floor is done by pouring hot Bombs, Antipersonnel. A small fragmentation
water over it and scrubbing. When a comparatively bomb designed for use against personnel. See
small amt of extriate is present on the exterior of fragmentation Bomb, under Bombs
bombs, it can be removed with acetone and the
bombs considered suitable for issue. Where ex- Bombs, Antisubmarine(AS) Designation of a British
cessibe exudate is present on the exterior of bomb med during WWII
bombs, the lots involved should be reported to the
Ordnance Ammunition Command, Joliet, 111 and Bombs, Antitank(AT). These were Brit ‘bombs(there
heId for disposition being no special US bombs) designed to be used
Each lot of bombs in storage must be inspected again st tanks or other armored vehicIes. Probably
each year for rust, corrosion, exudation and other general purpose (Gp) bombs were more suitable as
signs of deterioration, paying particular attention A/T than other types
to the condition of fuze wells and threads. If any Refs: A. B. Shilling, PicArsn; private communication
oily stains are observed on the surface of a (1961)
bomb container, it must be immediately opened and
the bomb examined for exudation. Bombs with a Bombs, Atomic. See Atomic(or Nuclear) Bomb in
large amt of exudation must be destroyed, as Vol l,p A499-L. Explosion of atomic bomb in the
briefly described under Bombs, Destruction of. earth atmosphere was discussed by H. Schwentek,
In addn to the inspection mentioned above, several Explosivst 1961,49-55
representative samples should be selected from
each lot and sent to the ballistic lab for testing. Bombs, Blast. See LC(Iight case) bomb briefly de-
All of these operns may be called surveillance scribed under BOMBS
Bombs are shipped in the same containers as
used in storage. Each container must be inspected Bombs, Blockbuster. See Blockbusters; also under
and any with oily specks must be removed and the BOMBS
bombs examined for exudation. Transportation of
bombs within the USA is goverend by “Regulations Bombs, Buoyancy(B) (Brit). See under BOMBS
for the Transportation of Explosives and Other
 B 239

Bombs, Breadbasket. See under BOMBS Bombs, Cobalt. Atomic or hydrogen bombs encased
in cobalt which, upon detonation, would be trans-
Bombs, British. Bombs used during WWII are brief- formed into deadly radioactive dust. These bombs,
ly described in conf “British Explosive Ordnance”, at present, are of theoretical interest inasmuch as
TM901985BI(1953), 1-158 & 178-204 they are considered too dangerous to use since
the dust would effect friend, foe and neutral alike.
Bombs, Butterfly. Small fragmentation or anti- In the detonation process, part of the Cosg is con-
60
personnel bombs verted to Co , a very radioactive substance
equipped with Refi Glossary of 0rd(1959),41
two folding wings
which rotate and Bombs, Conventional. Any nonatomic bomb designed
arm the fuze as primarily for its expl effect, as distinguished from
the bomb descends. a them, incendiary, leaflet or any other special
Designed to be purpose bomb
dropped in clus- Re/: Glossary of Ord( 1959),42
ters, the bombs
are frequently Bombs, Delayed Action. Bombs having a delay
fitted with anti- fuze which may vary from a fraction of a second to
disturbance or severaI days after impact. Bombs having short
delay fuzes delay fuzes are used to penetrate targets before
(See Fig) exploding; bombs having medium delay fuzes are
Re/s: I)Anon, used in low-altitude bombing to allow the plane
‘Ammunition to move away from the point of impact before
General’, TM deton; bombs having long delay fuzes are used
9*1900(1956), either to deny territory to the enemy for a period
168 of time or to aHow successive waves of planes
2)Glossary of to drop their bombs before any of them detonate
Ordnance(1959) A bomb which may be set to expI some time
41 after being dropped or planted is known as a
time bomb. Short-delay fuzed aerial bombs are
Bomb, Butterfly, 4.lbs usually not classified as time bombs
Re/: Glossary of 0rd(1959),42 & 44
Bombs, "Buzz". Brit colloquial term for the Ger
WWII flying bomb V~l(Vergeltungswaffe Eins) Bombs, Deep Penetration(DP) (Brit). See under
(Revenge Weapon 1) so named for the buzz-like BOMBS
noise of its pulse-jet engine(Ref 1). Officially
the bomb was known in Germany as F ZG-76 and Bombs, Demolition. Former classification for bombs
in the US it was designated as JB -2 Bomb. For its that exploded after short penetration, accomplish-
description see Refs 2 & 3 ing damage and destruction by both blast and under-
Re/s: l)F.Bellinger et al,IEC 38, 161-9(1946) ground explosion. A demolition bomb of WWII had
2)F.Ross,Jr,”Guided Missiles, Rockets and Tor- a charge approx equal to 50% of the bomb’s total
pedoes”, Lothrop, Lee & Shepard,NY( 1951), 14-20 wt. The present classification of such a bomb is
3)PATR 2510( 1958),pp Ger 213-15 GP(general purpose). See also under BOMBS
Refi Glossary of Ord( 1959)’,42
Bombs Carrying Paper Balloons(Japanese). See
under Balloons and Airships and Their Application Bombs, Depth(D) See under BOMBS
in War
Bombs, Drill. See under BOMBS
Bombs, Chemical. See under BOMBS. The Brit
desgn LC means “light case chemical bomb* Bombs, Dynamite. Makeshift bombs obtained by
tying several sticks of dynamite into a bundle
Bombs, Chemical Agent. Bombs contg a chemical Refi Glossary of 0rd(1959),42
agent as a main chge. See Bombs, Chemical under
BOMBS.
 B 240

Bombs, Earthquake. Large bombs when

which, such as the 4000-lb blockbuster and the depth bombs .
dropped, penetrate and explode beneath the According to Ref 2, they are GP(general purpose)
surface of the earth(as deep as 20ft) producing an bombs designed to produce max blast with chge wt
effect similar to an earthquake(Refs 1 & 3) ratio of more than 70%; aIso called ‘blast bombs”
According to Ohart(Ref 2), such bombs do more and ‘light case bombs”
damage after some penetration than they do if Re/s: l)Ohart( 1946),221 2)Glossary of 0rd(1959),
detonated in the open except possible for the very 43
large HC(high-capacity) blockbustens( qv), of 4000
-lb and larger which cover a greater area(in their Bombs, High Explosive. See Bombs, Explosive,
open-air blast effect) than a normal size bldg under BOMBS
Re/s: l)J .R.Newman, “Tools of War” ,Doubleday,
Doran & C0,NY(1943),362 2)Ohart(1946),204 Bombs, Hydrogen. See Vol l,p A499-L under Atomic
(or Nuclem) Bomb
3)Glossary of Ord( 1959),42
Bombs, Incendiary(lB). See Bombs, Chemical under
Bombs, Electron. See under Bombs, Incendiary,
BOMBS
Extinguishing of
Bombs, Incendiary(Extinguishing of). See under
Bombs, Explosive. See under BOMBS
BOMBS, the section which follows Bombs, Dis-
posal of
Bombs, Fission, See Vol 1,p A499-L under Atomic
(or Nuclear) Bomb
Bombs, Infantry Training(lT). Designation of a
Brit bomb
Bombs, Flash. See Bombs, Photoflash under
BOMBS
Bombs, Japanese Paper Balloon. See under
Balloons and Airships and their Application in War
Bombs, Fragmentation. See under BOMBS. Brit
designation is F
Bombs, Leaflet. See under BOMBS

Bombs, Fusion. Bombs that depend upon nucIear

Bombs, Light Case(LC). See under BOMBS
fusion for release of their energy. See Vol l,p
Note: Designation LC is also used for the Brit
A499, under Atomic(or Nuclear) Bomb
“light case chemical bomb’
Bombs, Gage. See Bombs, Dummy under BOMBS
Bombs, Magnesium. Incendiary bombs with magne-
sium as burning agent
Bombs, Gas. See Chemical Bombs, under BOMBS
(See also Bomb, Electron and Bombs, Chemical

Bombs, General Purpose(GP) See under BOMBS under BOMBS)

Bombs, Glide. See under BOMBS Bombs, Napalm. See under BOMBS

Bombs, Guided.Aerial bombs guided during their Bombs, Nuclear. See Atomic(or Nucle at) Bomb in
drop, in range and/or azimuth (See also Guided Vol 1,p A499-L
MissiIes)
Ref: Glossary of 0rd(1959),43 Bombs, Phosphorus, A chemical bomb filled with
phosphorus, especially white phosphorus.
Bombs, Heavy Case. Any HE bomb in which the See also Bombs, Chemical(Smoke) under BOMBS
wt of the casing is relatively large in proportion
Bombs, Photoflash. See under BOMBS
to the wt of the bursting chge
Refi Glossary of 0rd(1959),43
Bombs Pistol(Brit). See under Bombs, British
Bombs, High Capacity(HC). According to Ohart (Initiating Devices for)
(Ref 1), these bombs are the same as the LC
Bombs, Practice and Bomb Practice Target. See
(light case) bombs with a chge wt ratio of ca 80%,
under BOMBS
 B 241

Bombs, Robot Missiles carrying warheads, such as & other hydrocarbons, charcoal and castor oil
the Ger V-l(see PATR 2510,p Ger 213) or a flying could be used
bomb, launched from the surface and directed in Re/: A. Marshall, “Dictionary of Explosives”, Chur-
flight towards its target by an automatic pilot chill, London( 1920),15
or other automatic devices
Refi Glossary of Ord( 1959),44 Bond. The linkage betw atoms, represented by a
dot(.) or a Iine( - ) drawn betw atoms in a constit-
Bombs, Rocket. Aerial bombs equipped with rock- utional formula. Nature of the bond is considered
ets to give them added velocity and penetrating to be electrical attraction attributable to various
power after being dropped from an aircraft distributions of electrons around the nuclei of
Refi Glossary of Ord(1959),44 bonded atoms
Bonds may be divided into atomic and molecular
Bombs, Sabotage. Expl devices used by saboteurs types. Atomic bonds, in which each atom contribut-
to damage, destroy or injure personne I or property ed one electron, may be either homopolar(nonpolar)
Refi Glossary of Ord(1959),44 or heteropolar(pol ar). In homopolar bonds the elec-
tron pair is held equally by both atoms, so that no
Bombs, Semi.Armor.Piercing(SAP). See under difference in polarity exists; whiIe in heteropolar
BOMBS bonds the electron pair is held unequally, hence
the atoms differ in polarity. Molecular bonds are of
Bombs, Service See under BOMBS one type in which one atom contributes both ele c-
trons. This is the coordinate (semipolar) or dative
Bombs, Smoke. See Bombs, Chemical under BOMBS bond. For comprehensive discussion of this sub-
ject, see L. Pauling, ‘The Nature of the ChemicaI
Bombs, Target Identification(TI). See under BOMBS) Bond and the Structure of Molecules and Crystals”,
CornellUnivPress, Ithaca, 1st ed(1939),429pp; 2nd
Bombs, Time. Aerial(or other) bombs that may be ed( 1940)450pp; 3rd ed( 1960),644pp; L .P auling,
set to expl sometime after being dropped(or planted). “La Nature de la Liaison Chimique et la Structure
Short-delay fuzed bombs are not usually classified des Molecules et des Cristauz” ,PressesUniv,P aris
as time bombs(see Bomb, DeIayed Action) (1949),430pp
Re/s: l)Hackh’ s(1944), 137-8 2)The Van Nostrand
Bombs, Torpedo(Bombe Torpedo in Ger). Missiles Chemist’s Dictionary, Van Nostrand, Princeton
designed in Germany during the closing years of (1953 ),90-1
WWII. They resembled in appearance torpedos.
When launched, they travelled the greater portion Bond Energy. A measure of energy recad to disrupt
of the distance to the target(a ship) through the a chemical bond. The definitions as used in phvs
air and then would enter the water just short of them are discussed in Refs 1 & 2
the target and continue in the direction of their Refs: l)H.A.Skinner & H. D.Springall,Nature 162,
flight in air due to their momentum, in the 343-44( 1948) 2)L.I-LLong, Nature 162,344-45(1948)
same way as a torpedo. To prevent them from
going too deep before deton, a relatively flat angle “Bonderizing”. A trade mark process for furnishing
of entry into the water was necessary. The a corrosion-resisting base for paint finishes on
weapons are briefly described in TM 96198%2 steel, Al, Zn & their alloys and die castings
( 1953),445 Re/s: l)T.Lyman,Edit, “Metals Handbook”, AmSoc
for Metal s,Cleveland( 1948),733 2)condChemDict
Bombs, Uranium. Theoretical atomic or hydrogen ( 1950),105
bombs(See Vol l,p A499-L) encased in Uranium,
which, on deton, wouId be transformed into deadly Bonding. The act of joining together soIid materials
radioactive dust such as pieces of paper, wood, plastics & metals,
Refl Glossary of Ord(1959),44 by means of glue, cement or resins. Bonding can
also be achieved by means of fusion, such as in
Bomlit. A Ger blasting expl manufd after WWI by sintered metals
Wolff & Co at Walsrode. It contained K perchlorate, See also Adhesives in Vol l,p A102-R and Bind-
AN, TNT and guncottort. Other ingredients, such er or Agglutinant and Bonding Agents in Vol 2
as K & Na nitrates, starch, vaselin, naphthalene Refi I)See under Adhesives,Vol 1; and under Bind-
 I

B 242

er or Agglutinant and under Bonding Agents, Vol PATR 1685( 1948) 1 a)W.T. McMichael,USP 2985055’
2 2)M.P acker,Monthly Progress Rept P-A2078, ( 1955) (Bonding of booster rocket propellant) 2)M.
June 19 to July 31(1957), Contract DA-36-034-501 J. Bodnar, ”Bonding of Explosives to hfetal” ,PATR
-ORD-67-RD(Bonding of HE’s to metals)(Conf) 2412(1957) 3)M.J.Bodnar et al, ‘Adhesive Bonding
3)D.V.Clifford, ERDE,GtBrit,TechMemo 8/M/59 of High Explosives to Metals’’,PATR 2538(1958)
(1959)(Case bonded colloidal ProPlnt) 3a)M. J. Bodnar & E. R. Kelly, ”Adhesive Bonding of
Newer Typesof Plastics, PATR 2575(1958) 4)hf.
Bonding Agents or Adhesives for Ordnance. Bond- J. Bodnar et al, ‘Adhesives for Bonding High Ex-
ing agents or adhesives are being used success- plosives to hfetals and Uranium to Steel’’,PATR
fully in many ord applications where high strength 2613(1959) 5)M.J.Bodnar, ”Adhesives for Ord-
performance applications are reqd. Numerous mis- nance”, Ordn 44,954-5(1960)
siles, including Army’s Hawk, Lacrosse & Nike,
and the Air Force’s Boma”rk have vital components Bonits, Swed military underwater expls developed
joined by adhesives by AB Bofors, Nobelkrut, Bofors. The following
Adhesives offer a number of advantages over mixts existed before WWII:
mechanical means of attachment: a)they allow
TNT
relatively uniform distribution of stresses over the Boni ts For
entire bonded are a b)present aerodynamically Composition 1 2 3* Comparison
smooth surfaces c)give high strength-to-weight
ratio d)can be used to join components with com- TNT %) 30 40 100
plex geometric configurations e)can join thin RDX 50 70 60
sheets f)provide effective seals against moisture Properties:
fuels, chemicals & gases g)dampen vibrations and Loading Density, ~cc 1.68 L78 . 1.60-1.65
h)increase elec resistivity Heat of Expln,cal\g 1130 1200.1250 . 850
Several important types of adhesives used to Vel of Deton,m/sec 7600 7800 - 6800
obtain high- strength bonds are the epoxies, epoxy Rel Brissnce 136 - 100
-phenolics, nitrile-phenolics & vinyl-phenolics Gas Vol,l/kg at NTP 950 - 630
Some specs under which the se structural adhe- Power try Trauzl
sives may be procured are: MIL-A-5090B, “Adhesive .Block, cc . 421 . 290
Airframe, Met al to Metal”; MIL-A-8431, “Adhesive, *No props given in Ref 3
Heat Resistant. Airframe Structural, Metal to Metal’), 7.
MIL~A-8623A,’‘Adhe sive, EPOXY Resin, Metal to Metal During WWII some Al powd was incorporated in
Structural Bonding”; and MIL-A-14042, “Adhesive, Bonits and this increased their efficiency for
Epoxy”
The best approach to achieving good performance underwater explns. The Swed aluminized expls
were, according to Stettb acher(Ref 2), more
in bonded joints is to select the proper adhesive,
design the joint properly for the specific applica- efficient than the Ger urrierwater expl of WWII,
tion, and maintain rigid process control. One dis- which consisted of TNT 55.7, HNDPhA 27.9 &
Al 16.4%. See PATR 2510( 1958),p Ger 212, under
advantage in the use of adhesives is the absence
Unterwassersprengstof fe(Underwater Explosives)
of good non-destructive tests to determine the
strength of adhesive-bonded joints in a wide variety for addnl info on Ger expls
of ord applications According to Stettbacher(Ref 2) Bonit is one of
Data have been obtained at PicArsn on the ad- the best types of underwater expls
Refs: l)Anon, ”Bonit”,SS 30,332-3(1935) 2)A.
hesive bonding of HE’s to themselves and to other
adherends. The expls investigated include 75/25 Stettbacher,Protar 9,38 & 41(1943) 3 )A.Stettbacher
cyclotol, RDX-polystyrene & HMX-cellulose nitrate (1948),66
compns. Whether the bonded expl assembly was
tested statically or dynamically, failure always Bonocord. See Bofors Detonating Cord
occurred in the expl, never in the adhesive. If
proper adhesives & bonding procedures are used, Booby Trap. Devices which are installed to operate
failure should occur in the expl against personnel in territory surrendered to the
The ArmyOrd pamphlet on adhesives, ORD-P-20 enemy are called booby traps. They are designed
-306, is a useful ref in providing addln info on to function by themselves and to harass or destroy
bonding agents individuals or small groups of the enemy. The same
Refs: l)S.J. Lowell, ”Bonding Agents for Ordnanc~” device may be used for either art antipersonnel

—.
—...—
‘1
 B 243

mine or a booby trap. The classification is detd by also granulated with a NC-camphor binder
the purpose for which the device is installed Refi ChemicaI Corps Specification, CmlC Formula
Both the antipersonnel mine and booby trap are B2-5 O
more important for their psychological effect on t~ Note: Information obtained from W. W. Reaves & K.J.
enemy than for the number of casualties they cause Carlon,Army Chemical Center, CRDL ,Md
They strike unexpectedly, and oft~n when the
soldiers are relaxed in occupied areas or
doing some routine task. Mines and booby
traps shouId have infinite variety in their dis- BOOSTER
tribution and use and should be particularly (Beiladung in Ger; Relais or Dr%onateur s~condaire
dangerous to those who attempt to locate or in Fr; Carica di rinforzo, Carica d’accencione or
remove them Accelerate di esplosione in Ital; Promezhutochnyi
In addition to std antipersonnel mines, detonator in Ru~ \Carga de inflamacidn in Span)
fragmentation hand grenades, demolition blocks According to Marshall 2(1917),527, the Brit
and other adaptable ammunition items may be name is ren/ort or booster. Glossary of 0rd(1959),
used as either antipersonnel mines or booby 133 calls the Brit booster or auxiliary detonating
traps by theit being fitted with std firing de- fuze the guirze, but it seems that this term must be
.
vices. These include pull firing, pressure firing, applled only to the booster container and not to the
combination firing & release firing devices(Refs entire booster. All& EnExpl(1946),p 165, calls it
2,3 & 4) exploder, but judging by drawings of some Brit
Booby traps are also used during maheuvers fuzes, the exploder consists of booster and deto-
and in troop training where there is the need nator chges. The term magazine seems to mean
for a “safe” booby trap. Lt Day(Ref 1) has the same as exploder container or gaine. In some
reported the design and construction of a Jap fuzes, the term gaine was used for the HE
simple & efficient “trap” used to great advantage container loc Ated betw the detonator and the
in training personnel. Once constructed this trap booster(see Fig 10 l,p136 in Ref 14 and Fig 304,p
may be used over and over again. Flash simtdator, 381 in R.ef 15), but in most Jap ammo the term gaine
illuminating simulator & whistling simulator type is reserved for the booster container
booby traps are special devices used to provide When a HE, such as TNT, PA, Amatol, Comp B,
training in their installation and use and to en- etc is used as the m ain(bursting) chge in a missile
courage caution by troops exposed to booby traps (shell, bomb, rocket, torpedo) and is not sensitive
set by the enemy(Ref 5 ) enough to be activated by ordinary detonators, an
Re/.s: l)lst Lt J. K. Day, The Ordnance Sergeant, expl intermediate in sensitivity betw initiating and
The OrdnSchool,APG,Md( 12July 1943 ), 117-18 main expl chges is introduced betw them. This expl
2)Anon, “Ammunition Inspection Ciuide”,TM9*1904 (such as pressed RDX, Tetryl, PETN, HNDPhA,
(1944),240-8 3)Ohart(1946),363 & 367 4)Anon, etc), called booster explosive, will readily deto-
“Military Pyrotechnics”,TM 9-1981(195 1), 142-7 nate from the action of the initiator and develop
5 )Anon, “Use and Installation of Boobytraps’’,FM enough energy to ensure high-order detonation in
5=31(1956) the less sensitive main chge. The same effect can
be obtained by using larger amts of initiating
Books on Explosives, Propellants, Pyrotechnics (primary) expls(such as MF, LA, or Tetracene) but
ond Related Items. See list in Vol l,p A676 and this is not advisable because their high sensitivity
Additional List at the end of Vol 2 to shock and friction makes them very dangerous
to handle in large amts, as well as rendering the
Boom Powder. A casual name for an ignition mixt round more susceptible to premature expln. Also,
designated B2-50, and used in Fuze, Grenade, Ig- they are much more expensive and more difficult
nition,M201A 1, to ignite chemical munitions, Upon to manuf than expls Iike Tetryl
ignition, the mixt produces a large number of incan- Press-Ioaded Tetryl has been used in most US
descent particles. The original mixt, developed at boosters, but RDX is used in some newer types(Ref
Army Chemical Center, Md, contained: Pb chromate 20). One US bomb fuze, namely the M111A2 Nose
60, Mg20 & Si 20%. This formulation was granulated Fuze, contained a BkPdr booster(Ref 7,p 270).
with a NC-camphor binder. The original mixt has Some US Navy boosters contained pressed PA(Ref
been replaced by a later compn consisting of: 8,P 93). The booster housing(corstainer) may be in
red Fe oxide 50.0, powd Ti 32.5 & powd Zr 17.5%, the shape of a cup or of a long cylinder closed at
 B 244

.
the bottom. The containers flRIKER m6LY

ate usually screwed directly The French

FIRlffi PIN

to the fuze and become an and Japanese

FIRING PIN < 5PRlr46

intergral part of it or they may \ used compress-

thdy & be imbedded separately in the ““’M c-’w\A ed PA. The
Booster
main chge of a missile; then ““---l Russians, as

r
Assembly ARMING PIN

US Bomb the detonator is imbedded in late as WWI,

ARMING PIN SPRING’
Nose Fame the booster chge. Boosters used pressed
WIDER MN
Ml 71 that have a self-arming dry Guncotton
-4
feature are considered as as boosters
““’’ ------

auxiliary -/uzes. , If an ordinary booster is not ““”’’O’--+

in warheads
sufficient to guarantee high-order deton of a very
SLICfR SPRING+
of some tor-
large bomb, an addl booster, called auxiliary %IDER PLVG — pedoes with
booster (sometimes called sub-booster) BcaTfR LEAD,N
+,
wet guncotton
is attached to SLIDER LCCK as bursting
ARMING VAN

\ { 6 the main boosters SwJER LmK 5PRING chge and pres-

-+
(Ref 7,p 249). sed TNT for
‘~ In many cases shells contg
an auxiliary US Bomb, Nose Fuze ‘?lith Booster c ast TNT. They
booster is re- also used PA
quired to ensure The Italian boosters used during WWII in HE shells
high-order deton ,smnm were of two types:
for very insen- a)The older system con
sitive expls or sisted of a metal tube,
to do the same contg compressed Bal-
in the event that listite and provided
‘m a bomb bre al& with a flash hoIe at

u
upon impact each end. The tube
ECOSIER
(See Figs)

r
was fitted below with
During WWII a PDF(point detonating
ltolion
the British used fuze) and had under it
US Bomb Nose Fuze Mechanical
Arming Type With Booster
either compres - Impact a larger chge of B al-
ed Tetryl or a Nose Fuze listite contained in a
combination of compressed Tetryl and TNT(Ref With 3aoster
metal tube with a flash
A
8,p 165), but prior to this they used com- hole at the top only
pressed PA(Ref 4). The info about their current /
b)The later system,
uses is classified c ailed detorzatore ad
alto esplosivo, M35 o
M38, used in shaped

‘--
E&II
9 BLK. F.w.vfm

Iz.b-’‘“L=
M,38

Booster,
Detonator
igniter and
Units,
m
4-
$

).,4>
.7‘.
‘+

Used With Mechanical Time

and Other US Fuzes
).4!s3

,— ———-
 B 245

-chge projs, consisted of two parts, an upper and a steel plug

)—.—
lower. The upper part, which was fitted(by means which fit-
of a collar) below the regular PDF, consisted of an F ted into
TAIL,JWT

Al cylinder with a tube inserted in it. The tube corr the ad ape
tained a layer of RDX(serving as a base chge) and er. Above
a layer of LA(serving as a primary chge). The the aux-
lower part of the booster contained several pellets French, I iliary
of TNT wrapped in oil paper (Ref 16,pp 61-3 and l-kg Mortor booster,
Lomb With
Figs- 72 & 73) ( - s. ExPL051vE CAVI T\ the boosr
Nose Fuze
The Italian ond Boosterj ‘i ! er lead-in
booster container pellet was
used during WWII located
in bombs was either and it had a
relay or delay
::, type. The long boost- pellet be-
‘: er consisted of a low it.
For the
.----_NOSC 1MP4c? F UZE
definition
~;~, ~ closed at one end; of adapt-
the short type was er-booster
a similar tube 4.8”
See Vol l,p 102-L
Japanese
; tube was screw Goine for .PRIuER Illustrations
Skipping of some
‘.,.~ ~-threaded at the L(VA
Typical Italian open end to take - DSLAY foreign

.~
PAPER WASHER
Boosters - RELAY
an adapter and boosters,
d A
contained two r except
,compressed blocks German
S(it BIX6TER~

.
!7,.. of T-NT below ones, are
.’
G included.
., the adapter; the
J upper block was
“;(: Illustrations
,, of Ger
~J:\; recessed to take a

!
.. ,, ~ booster. The short boosters
,, ‘f?.
.. ~ booster was similar are given
.,.—
.“
! ;+ , but contained a
smaller chge. Dif-
in Refs
12,13 &
17

F
lj ferent types of
.
,!
.— - adapters were
.
fitted to the booster
to give delay action,
.J
J.
or different length
projections of the
11 ““- auxiliary booster Refs: l)Marshall 2(1917 ),527-8 (Boosters or “ren-
which fitted into the forts” consisting of TNT loaded in brass tubes 4“
booster proper. The long and of a diam slightly larger than the detona-
auxiliary booster was tors ) 2)F .Olsen,ArOrdn 3,269-72(1923) (Brit
the same for both boosters prior to WWI contained loose PA. This
types. It consisted was gradually replaced during WWI by Tetryl,
of an Al tube, the top of which was threaded to a
known in GtBrit as CE. When the US entered the
war, it adopted Brit boosters) 3)Marshall 3(1932),
162-3 (Brit Army gaine was a strong steel tube ca
3“ long& 1/4” wall thickness, which was screwed
into the mouth of a shell. At the top there was a
 B 246

pellet of Bkpdr with an axial perforation. This was PA pressed to d 1.10 in Kraft paper tubes 30mm in
ignited by the flash from a fuse, which was screwed diam) ll)Anon, UBritish Explosive Ordnance” ,TM
9. 1985s l(1953),(Conf) 12) Anon, “German ExpIosive
@UCKKMEti UIXIUW oETc@mToR
Ordnance”,TM 9-1985*2(1953), 125,138,156,179,185
& 188(Bomb boosters) 13)Ditto,TM 9*1985fi(1953]
390,400-1,406-7,410-22,425 ,427,429-35,437-8,440,
HEW* 442-5,45 O-8,46O-l,466-8,472-3,482,488-9O,5OO,5ll,
rlN Fi31L STRIF_ 516-18,521-2,552 & 562( Shell boosters) 14) Anon,
COPPER CUP — “Japanese Explosive Ordnance”,TM 9*198$4(1953]
FuLMIMA?E OF NERWW— 22,122,125-6,128 -33,136-7,139-43,145 -l48,l5O,l52,
FEIT WASHES— 158,173,175 & 190-201 (Bomb boosters) 15)Ditto,
TETRYL TM 9*1985*5 (1953),281-3,304,308,319-20,322-3 1,
BRASS CONTAINfR
w ----- A
336;340-4,373,378,380- l,384-9,39l-8,4OO-5,4O9,4l9
. ...~
COPPER PLUG Japanese -23,436,46 1,468,470,473-6,48 l-2,485,489-92,497-9,
COWER CUP CWR Army 503,506-8,521-5,528-32 & 541-2( Shell boosters)
131MX POWER MIXTURE ‘sines 16)Anon, ”Italian and French Explosive Ordnance”,
{Eaoster+
Tllf FCJIL STFtt9 TM 9*1985”6(1953),3,8,28,39,44,48 & 52(Ital bomb
COPPER CUP boosters; 61-3 & 81(Ital shell boosters); 178-9,
FULMI NATE OF MERC#W- 183,190,196 & 205( French bomb boosters)
17)PATR 2510( 1958),pp Ger 20-1 18)US Specifica-
FEL.T WSNER ,
TETRV1
tions: MIL-B-12739(Booster, auxiliary, T33E 1;
“{
BRAS CONTAlftE8 ~
loading, assembly & packing); MIL-B - 14316)(Boost-
er,M21A4 & M25; Ioading, assembly & packing);
MIL-B-20474 & MIL-B-20360(Booster, M22; metal
parts for, Ioading,assembly & packing); MIL-B-
20492 & MIL-B-20359(Booster, M24 & M24B1;
over the gaine. This pellet passed a more powerful metal parts for, loading, assembly & packing);
flash to an open capsule contg MF situated im- MIL-B-20394 & MIL-B-20392(Booster, M25; metal
mediately over two tetryl pellets. The bottom of the parts for, loading, assembly & packing); MIL-B
gaine was closed with a cap strong enough to with- 11507A(Booster,M120; loading, assembly & pack-
stand the considerable forces that arose when the ing); MIL-B- 13675 (Booster, M123; loading, as-
shell was fired from a gun. The shell was filled sembly & packing); MIL-B-13674 & MIL-B-12830
with Amatol the center of which contained a long (Booster, T35E7; metal parts for and loading, as-
cylindrical cavity lined with cast TNT. A bag sembly & packing) MIL-B- 11627 & MIL-B-1 1615
with tryst TNT was placed on the bottom of the (Booster, T36E2; metal parts for and loading, as-
cavity and the Tetryl end of the gaine was pressed sembly and packing) MIL-B-1099fiBooster,T 1208
firmly onto the TNT. With this arrangement, MF (N120); metal parts for] 19)A. B. Schilling,PicArsn;
detonated Tetryl from which the deton wave private communic ation( 1962) 20) P. Varrato,PicArsn;
passed to tryst TNT, then to cast TNT and finally private communication 1962)
to the main chge of Amatol) 4)Marshall 3(1932),
172-3 5)Hayes( 1938),6,39,595-6 & 606 5a)W.R. Booster Rocket. Any high-thrust unit or assembly
Tomlinson,Jr,PATR 13 11( 1943) (Some foreign boost - that fires at take-off to get a missile(such as a
er and HE’s compns) 6)Anon, RAmmunition Inspec- rocket, bomb, shell) or an unmanned or manned air-
tion Guide”, TM 9s1904(1944), 19,124-30,267,399-403, craft, to which it is attached, started along its
444,473,495-7 & 569 6a)L.H.Eriksen, PATR 1446 trajectory. Usually, a booster rocket produces a
( 1944) (Some foreign booster and HE’s compns) much greater thrust than the 2nd stage or sustained
7)Ohart( 1946),19-20,36,122, 165-9,217-19,225-7,249 power plant of a rocket. Booster rockets are usually
262-3,270,281 & 338 8)All&EnExpl(1946), 163-6 propelled by a solid propellant(such as in the Nike
8a)P. F .Schaeffer,PATR 1677( 1948)( Development -Ajax missile) but liq proplnts are also used. The
of improved boosters) 9)Anon, ‘Artillery Ammun- booster rocket should not be confused with ATO,
ition”,TM 9s1901( 1950),310 & 369-76 10)L.M6dar~ JATO or RATO engines although there is a con-
MP 33,339( 1951) ( “Relais” of pressed 95/5 mixt of siderable similarity in design. A liquid-propelled
PETN/Mononitronaphth alene, d 1.60, was found to booster rocket is used when the requirements are more
be satisfactory; as was also the “relais” of tryst extensive than normally available from solid-pro-
 B 247

pelled units. The term /ir.st-stage engine is recom- good fire retatdant(Ref 4) (See Borax) (See also
mended for those designs where the booster unit Spec MIL-S-11159 amd Ref 4a for methods of
is usually large and is completely expended analysis)
during the 1st stage operation Trimetbyl Borate, (CH,&BO,; mw 103.92; Iiq, fr p
Re/s: l)A.J .Zaehringer, “Solid Propellant Rockets: -29°, bp 68.7, fIash p 32°F, d 0.923, vap press 90mn
AmerRocketCo, Wyandotte, Mich( 1955 ),2 2)Rocket- at 60°F; decomposes in w (Ref 6)
Encycl(1959),54-8 Zinc Borate,,3Zn0.2B203; mw 383.42; wh amor
powd or triclinic trysts, mp 980°, d 3.64( amor) &
Booster Sensitivity Test. See Vol l,p VIII. More 4.22(cryst); used as a fungicide(Ref 5,1267)
detailed description was given by L. Goodman in Sax(Ref 5,377) reports that berates in general
“Physical Testing of Explosives”, Part III,OSRD are not highly toxic and therefore not considered
2746( 1945 ),6-7 as industrial poisons. Sodium borate is used in
medicine but accidental poisoning due to in-
Boracitol. A HE compn listed in Ordn Safety gestion of berates or boric acid has often occurred
Manual ORDM 7~224(1958),Tables 1904 & 1905,pp Re/s: l)Mellor 5(1924),47 & 65 2)Hackh’s(1944),
19-3 & 19-15 as Storage Compatibility Group L and 138 3)Kirk & Othmer 2(1948 ),600ff 4)P .Bernhard,
Explosive Hazard Class 9. The compn & props of IndVernice(Milan) 7, 113- 18(in Ger) & 119-2 l(in Ital)
this HE could not be found in std ref works, reports (1953); CA 47,11755(1953) 4a).S.Kaye,PATR 1947
or in Ord manuals ( 1953)(Determination of purity of Na tetraborate by
titration in non aqueous medium) 5 )Sax( 1957), 377
Boranes. See Boron Hydrides & 1198 6)M.H.Crompton & J .E .Reed, ‘Some Prop-
erties of High Energy Fuel Chemical Materials”,
Borates. A general term for salts of acids based Olin Mathieson Chem Corp( 1959),pl 17 7)Cond.
on boron, such as: rnetaboric HB02, perboric HB03, Chem Dict( 1961),459 & 1159 8)J.DeMent,USP
tetra- or pyroboric H2B40,, boric or ortboboric 2995526( 1961),p27
H$BOq and others. Props of various berates are
given in Refs I,3,5,6& 7 and their uses in some
Borax occurs naturally as tincal in the dried-up
pyrotechnic compns are listed in Ref 8
Following is the list of some berates: inland lakes of India, Tibet & California. Native
Ammonium Borate (Ammonium Acid Tetraborate), tincal contains ca 55% Sodium Tetraborate Deca-
(NH4)HB40,.3H,0, mw 228.37; CO1 trysts, mp decomp, bydrate, Na2B407.10H20; mw 381.44, mp 75°
d 2.6; used as a fire-retardant (Ref 7, p 71& Ref 4) (loses 8H20 a 60° & 10H20 at 2000), d 1.69-
Butyl Botate(Tributyl Borate), (C4H9 )3BOa, mw - L72(Ref 6); SI sol in cold w, v sol in hot w.
230.16, COI Iiq, bp 232.4°, d 0.855-0.857, flash p If a satd soln be allowed to cool above 620,
185° F(open cup), n~ ~.4071 at 25 °(Ref 7,pl159). octahedra trysts of the pentabydrate, Na2B407-
Its use as an ingredient of smoke-producing compns 5~0 separate
was patented by DeMent(Ref 8) See also Ref5,pl198 Since 1926 when the mineral ~ernite(Na2B40~ -
Calcium Metaborate, Ca(B02)2; mw 125.72, CO1 4H20) was discovered in Searle’s Lake, Calif, it
rhmb or long flat plates, mp 1154°(Ref 5 ,p 424) has been almost the sole source of borax in the
Cupric Metaborate, Cu (B02)2; mw 149.18; USA. Kernite is first extracted with hot w which
bl-grn trysts, d 3.859(Ref 5,P 515) dissolves borax; any silica in soln is pptd and
Ethyl Borate(Triethyl Borate or Triethoxyboron) the hot filtrate, after dilution, is treated with an
(C2H5~B03; mw 146.00; CO1 liq with mild odor, oxidg agent to destroy coloring matter. After
bp 120 , flash p 52° F, d 0.864 at 26.5°; toxicity further filtration, borax is obtd by crystn(Refs 3&
details unknown(Ref 5,p 668 & Ref 7,P 459). Its 4)
use in smoke-producing compns was patented by When heated, borax fuses, loses w and swells
DeMent(Ref 8) into a wh porous mass. Finally borax melts(anhyd
Lead Metaborate, Pb(B02)2.H20; mw 310.87; wh powd at 561°) and on cooling forms a clear glass.
powd, d 5.598( anhyd) (Ref 5,816) Borax “beads” fused in a loop of Pt wire are used
Magnesium Ortboborate, Mg3 (B03 )2; mw 190.60; as tests for oxides which dissolve in the bead
rhmb COI trysts, d z .99 at 21 °(Ref 5*P 841) and show characteristic colors
Potass”urn Meta~orate, KB02; mw 81.92; COI cryst~ Large quantities of borax are used in the manuf
mp 947-50°(Ref 5 ,1037) of enamels, glass, soap, drying oils and as clean-
Sodium Tetraborate,N~ B407; mw 201.27; wh trysts ing & stiffening agents in laundering, as a flux in
mp 741°, bp 157’5°(dec), d 2.367(Ref 5,1129); very soldering & brazing and as an antis eptic(Ref 2,
 B 248

3 & 4). Pearcy(Ref 1) used borax, together with Bore(noun). The interior portion of a gun barrel or
NaCl(or KCI) and KN03, as an additive to NG-NC tube which is in front of the breechblock, in-
expls Eo render them safe against fire damp. Car- cluding powd chamber, shot chamber, slopes and
bonaceous matter was avoided as far as possible the rifled portion of the tube(see also Barrel, Gun)
in such expls. One expl compn contd NG 42.5, NC Refi l)Glossary of 0rd(1959),45 2)Webster’s Un-
2.5, KN03 20, borax 20 & NaCl 15% abridged I)ictionary( 1961),255
US Specification requirements for military uses
of borax are given in Refs 5 & 7 Bore Diameter is the diam of the gun bore prior
Re/.s: l)A.C.Pearcy,BritP 7647(1914) & CA 9, to cutting the grooves therein. Since the latter
!, .
2593(1915) 2)Hackh’s( 1944),779 3)Me110r( 1946), are 0.003 to 0.005 m depth(sometimes up to
660-1 4)Partington( 1950),652 5)USSpec SS-B-61 IA 0.010”), bore diam is always materially less
( 1952)( Borax, sodium borate) 6)Sax(1957),374 than the “groove dam’’. Those portions of
7 )USSpec SS-S-535A( 1958) (Sodium borate, deca- the bore not cut away in fashioning the grooves,
hydrate, tech borax) 8)R.F.Gould, Edit ‘Borax and hence left projecting upward berw th e
to Boranes”, Advances in Chemistry Series No 32 grooves like ribbons of metal, are called lands.
American Chemical Society, Washington, DC(196 ~), Thus, another definition of bore diam is rhe dis-
240pp tance across the lands, that is, from the surface of
one land to that of another directly opposite
Borazole, B3N3H6; mw 80.53, N 52.18%; CO1 liq, Re/s: 1 )Hayes(1938),159 & 194 2) Glossary of
ftp -58°, bp 53°, d 0.824 at OO; some orher physic~ 0rd(1959),45,53 & 167
props are given by Eddy et aNRef 5); can be prepd
by interaction of LiBH4 & NH4C1 in the absence Boreholes or Blast HoIes(Trous de mine in Fr).
of SOIVS at mod high temps(Ref 3). Although the Holes made by boring or drilling, for the purpose
yields(30-35%) are of the same order of magnitude of confining a blasting chge making it possible
as those obtd in earlier procedures, this method, for the expl to develop max efficiency in break-
according to Schaeffer et al(Ref 3), is more conv- ing the surrounding material, are called boreholes
enient in that it does not use high pressure ~ or blast holes. These holes vary over a wide
high vac app and it does not re q the use of range of size and type and are drilled, by many
B2H6. A four-step procedure involving the re- different kinds of equipment, in alI conceivable
action of B *H6 with liq NH3 to give borazole directions from straight up to straight down.
is described by Rollier(Ref 4) who also studied Small holes (from 1 to 2.5” diam and up to 30ft long),
its structure in rock are usually drilled with percussion type
Sax(Ref 6) considers this compd to be moder- machines operated by compressed air. Similiar
ately high in toxicity and a dangerous fire holes in soft material such as salt, potash,
hazard, as them reaction can produce spontan- gypsurn & coal are drilled with augur machines,
eously flammable gases either mechanically driven or air operated
Schaeffer et al(Ref 4) found that NF14C1 causes For larger holes in rock(up to 3.5’’diam and
extensive decompn of borazole at 275 and above up to 40ft in length),the compressed air operated
The compds LiBH4 & B2H6 do not react appre- wagon drill is generally used. With the above
ciably with it. Boron halides react to give mono exceptions, practically all blasting for raw ma-
& dichloro- or bromoborazoles, some of the phys- terial production above ground involves the use
ical props of which are described by Schaeffer of large diam holes. MOSC quarries, open pit
et al. Some borazole compds are described by mines, ore mines & coaI strippings are in this
Wiberg et al(Ref 1), and an exhaustive review catagory. Blast holes in such operations range
of their mol structure, formation, phys & them from 5 to 9“, with a few locations as low as 4“
props is also given by Wiberg(Ref 2) and as high as 12”. These holes are vertical
Refs: l) E. Wiberg et al,Z AnorgChem 256,177 in most cases except in bituminous coal strip-
-216(1948) & 257, 133-44(1948); CA 43,5690(1949) pings where horizontal auger lmles(in the “high
2)E.Wib erg, Naturwissenschaften 35,182-8 & 212 wall” ) are commonly used. Some types of rock
-18(1948); CA 44,2882(1950) 3)G.W.Schaeffer formations can be blasted most economically by
et al, JACS 73,1612-14(1951) & CA 45,6951(1951) the use of coyote ttmnels(qv)
4)M.A.RoHier,Gazz 81 ,272-5( 1951) & CA 46,3444 Re/s: l)Daniel(1902),606-9 2) Blasters’ Hdb
(1952) 5) L. B.Eddy et al, JACS ~~,2105-6(1955) (1952 ),163-5
& CA 49,9993(1955) 6)Sax(1957),374
 B 249

Bore Prematures. See Explosions, Premature boric acid is now made from the naturally occur-
ring mineral colernanite(CazB601 , .5 H20)(Ref 3)
Bore Resistance. A term used in Interior Bal- and other miner,als (Ref 6)
listics which designates resistance to movements Boric acid M used in medicine as an antiseptic
of a projectile that takes place in the bore of a and large quantities have been used as a food
gun after the rotating band is engraved by the preservative. Its use for this purpose is now
rifling prohibited in many countries. Boric acid is also
Re/s: l)Corner,Ballistics( 1950),213-25 2)SAChf~ used in the manuf of glazes, particularly for
Ballistics(1951 ),l15 enamels to be used on metal s(Ref 3). Boric acid
has been used in expls, such as Boritines(qv).
Boresafe. This term is applied to a projectile Its use in smoke-producing compns was patented
when all of its detong elements are positively by DeMent(Ref 10)
separated from the booster by some form of inter- Refs: l)MeHor 5(1924 ),47ff 2)Hackh’s(1944), 138
ruption while in the bore of a weapon 3)Mellor(1946),659 4)Kirk & Othmer 2(1948),602
Refi Anon, “Ammunition Inspection Guide’ ,TM 5)P artington( 1950),65 3 6)Faith,Ke yes & Clark
9.1904 (1944),322 (1957),161 -4 7)Sax(1957),375 8)M.H.Crompton
& J .E .Reed, “Some Properties of High Energy
Bore Safe Fuze. Certain fuzes are considered to Fuel Chemical h4aterials,01in Mathieson(1959),p 10
be boresafe(detonator safe) if the expl train is 9)US Spec hLS-36038(May 1960) 10)J.lleMent,USP
interrupted so that, while the projectile is still 2995526( 1961),p 28
in the bore of the weapon, premature action of
the bucsting chge is prevented should any one Borides are binary compds of neg boron with a
of the more sensitive elements (primer or aer- more p,ositive element or radical of the type
onator) a ccidently function(Refs 1,2, & 3). M3B or BR~(Ref 2). They are prepd by electrolysis
This term is sometimes applied to fuzes that, of corre spending berates with addn of fluorides
due to design, have never functioned prematurely at about 1000°. Andrieux(Ref 4) successfully
(Ref 21 applied this method to making TiB2, La136, NdB6,
Re/s: l)Anon, “Ammunition General” ,TM 9c1900 GdB~, YB6, ErB6, ThB5, VB2, Cr3B2, UB4,
(1946), 107; (1956),134 2)Ohart( 1946), 123 MnB~ ZrB4, TaB2, CbB2, h40B & WB. Calcium
3)Anon, “Artillery Ammunition”, TM 9*1901(1950), boride, (CaB6 ), is made by electrolyzing 2
243 CaB204 + CaF in a smaIl carbon crucible; borides
of other alkaline earths are made in the same
Boric Acid(Boracic Acid or Orthoboric Acid), way. For making Ce borides, it is more advantag-
H3BOg; m w 61.84; wh triclinic trysts or powd, eous to use alk earth berates with a small amt of
mp l~5°(dec), loses 1.5H20 at 300° d 1.435 Ce02(Ref 4). The mechanism of electrolytic prepn
at 15 ; S1 sol in cold w; more readily sol in hot of borides of difficultly fusibIe metals was studied
w, alc or glycerin; made from borax by adding by hieerson & Smirnov(Ref 10). Lfontgomery(Ref 6)
HCl or H2S04 to a hot coned soln and crystg patented a process for the making of tryst boricles
the prod by cooling(Refs 1,2 & 5). Sax(Ref 7) by he sting CB4 with one or more of the elements
considers boric acid as moderately toxic but re- (Ti, V, Cr, Zr, Nb, Mo, Hf, Ta & ~’) at 1900°
ports that fatal poisoning of children has been under a press of 1000 lbs/in2. Meerson & Samsonov
caused by accidental substitution of boric acid (Ref 9) prepd borides of high-melting metals from
for powd milk. The fatal dose of orally ingested mixts of metal oxide(of Ti, Zr, Nb, Ta & lV) with
boric acid for an adult is somewhat more than C34 & Iampblack by a vacuum-thermal process
15 or 20g and for an infant 5 to 6g A review of the chemistry of borides has been
Several boric acids are known(at Ie ast in the reported by Brauer(Ref 5), Kieffer(~.ef 7) and
form of salts), all derived from boron trioxide, Samsonov & hfarkovskii(Ref 11)
with varying amts of water: Richardson(Ref 8) in a review of the application
Orthohotic acid H3B03 or B203.3H20 of borides and other materials noted that boride
Metaboric acid HB02 or B203 .H20 -type materials, although brittle, may be useful
Tetraboric acid,H2B407 or 2B203 .H20 as components of rocket engines
Re/s: I)hiellor 5(1924 ),23ff 2)Hackh’s(1944),138
Of the free acids, orthoboric is the only important 3)Kirk & Othmer 2(1948),5%2 4) J. L. Andrieux,Rev -
one. A large proportion of the world’s supply of M6t 45,49-59(1948); JFourE1ec !57,N0 3,54(1948)&
 I

B 250

CA 42,8089(1948) 5) G. Brauer, FIAT RevGerSci nitroglycerin), “Hi-Ve locit y“ Gelatin, “Red

1939-1946, InorgChem Pt II, 1948, 100-8 & CA -Cross Extra”, “EL-389-B* (desensitized NG),
43,3329(1949) 6)H.R.Montgomeqt USP “SOWE”(special oil well expl) No 1 & No 3 and
2613154(1952) & CA 47,2674(1953) 7)R.Kieffer, “EL-431-A”(cast, non NG expl). hfethods of
P lanseeP roc 1952,268-96(1953) & CA 4710438 well shooting are described in Ref 2,pp 443-50
(1953) 8)L.R.Richardson, Sr,AmerCeramBull 33, Digging of pole holes(Ref 2,pp 422-3), ex-
135-7(1954) & CA 48,8506(1954) 9)G. A. Meerson & cavation (Ref 2,p 365), ditching (Ref 2,p 379)
G.V.Samsonov,ZhPriklKhir 27,1115-20(1954) & and some other drilling operns can be facilitated
CA 49,6757(1955); Ibid 27, 1053-7(1954) (English by the use of expls
translation) & CA 50,6988(1956) 10)G.A.Meerson (See also Seismic Exploration or Prospecting)
& M.P .Smirnov,KhimRedkikhElementov,AkadNauk Refs: l)Daniel(1902),722, under “Sondage’
(Russia)InstObshchei i NeorgKhim 1955,N0 2, 2)Blasters’ Hdb(1952), 365-410, 417-24,& 443
130-47 & CA 50,3122(1956) ll)G.V.Samsonov -50
& L.Ya. Markovskii,UspekhiKhim 25,190-241
(1956) &CA 50,8359(1956) Boritines. Safety expls, patented in Fr in 1887
by Turpin, consisted of: a)NG 37.5, kieselguhr
Boring, Use of Explosives in. Boring operations 12.5 & b o ric acid 50% and b)KCIOa 35, boric
may be considerably facilitated if expls are used acid 50, J)N!3 5, charcoal 5 & coal tar 57.
to destroy hard objects, such as stones, broken Ref: Daniel(1902),77
boring bits, etc obstructing the progress of the
drill. One of the first applications of expls for Borland Powder. An expl prepd in England by
such operations was made in France by Brunet impregnating NC with a soln of K or h’a bichromate
and the method was described by Haton de la drying and treating it with a soln of a Ba salt.
Coupilli$re in Ann ales des Mines [7] 16,5(1879) This caused formation of BaCr207 which de-
Lipmann, of France, facilitated drilling for posited inside and outside the NC fibers. The
the foundation of a column by first softening the resulting mass produced a smokeless powd which
ground by exploding small charges over multi- could also be gelatinized
tubular cutters. Jandin used a similar idea during Ref: Daniel( 1902),78
the construction of Palma del Rio bridge over
Gudalquivir, Spain. Roberts of the USA made a Borland’s Method of Manufacturing Smokeless
fortune in the Pennsylvania oil fields from the Powder. In 1901, Mr Borland, Director of EC
idea of exploding charges of NG or dynamite Powd Co, Ltd, England, invented a procedure
near the bottom of completely exhausted oil wells. in which NC was gelatinized by an emulsion
For this, he either poured some NG into the well contg MeOH, acet, camphor, paraffin oil &
or lowered into the well a tin cartridge of dyna- benz or ligroin. The vol SOIV was removed by
mite provided with a blasting cap. Explosion in moist air heated at 65.5° . The moisture in the
both cases was initiated by dropping a weight air was used to prevent formation of static
(called a “go-devil”) from the top of the well. electricity y
This method caused the ground near the bottom Refi Daniel(1902),78
of the well to crack and if there were any oil
in the vicinity, it would flow toward the bore Borlinetta Powder. An expl compn patented in
hole thus rejuvenating the exhausted well(Ref 1) 1867: PA 35.1, NsN03 35.1 & ~Cr04 29.8%
The method used by Roberts is known now as Refs: l)Daniel( 1902),79 & 626 2)P6rez Ara
“well-shooting” and is practiced not only in (1945), 220-1
petroleum, but also in water and gas wells.
As NG is very dangerous to handle, many pre- BorneoI (Also called Bornyl Alcohol, Baras
mature explns took place in the past, causing Camphor, Borneo-Camphor, 2-Camphanol, d-
the loss of Iife and property. Because of these -Camphyl Alcohol, 2-Hydroxy-C amphane or
facts, the DuPont Co has worked for years Sumatras Camphor), C ,OH ,70H; mw 154.24,
towards the complete elimination of Iiq NG in 0 10,37%; transparent hex Ifts, mp 108°, bp
its well shooting activities. This goal was 212°, flash p 302°F (Closed Cup), d 1.011
finally achieved beginning in 1951 and NG has at 20°; sol in alc or eth; v S1 sol in w. It is
now been replaced by a series of better and a terpene either obtained from the Dryobalanops
safer expls, such as ‘DuPont SNG” (solid Camphora fruit or prepd synthetically. It is used
in perfumery, celluloid manuf & in medicine as and delay compns using amorphous B are listed
an antiseptic or stimulant by Ellern(Ref 14a)
Refi l)BeiI 6,72,(47)& [80] 2)Hackh’s(1944), (See also Boron Explosives, Boron Hydride Fuels,
139 3)SSX(1957),375 Boronites, Boron Solid Propellants and Borotorbex)
Re/s: l)MeHor 5(1924), 1-23 2)Gmelin,Syst Nr 13
Börnstein, Ernst (1854-1932 ). Ger professor of (1926), 1-53 & (1954), 1-96 ‘3)Thorpe 2(1938),34-40
chemistry at Strassburg and Berlin. His doctor’s 4)Hackh’s( 1944), 139 5)Kirk & Othmer 2(1948),
thesis was a contribution to research on bitoIyl. 584-88 6)Partington( 1950),654 6a)G.A.Noddin &
He did important work on the decompn of coal C. P. Spaeth, USP 2717204 (1955)& CA 50,2174
and other solid fuels. His brother, Richard (1956) (Use of B in elec bIasting caps)
Bernstein, is co-author of Landolt-Bernstein 6b)Ibid, GerP 941473(1956)& CA 52,15072(1958)
Refi F. Frank, AngChem 45,289( 1932) (Use of B in primers with deIay action) 6c)coIl,
“Soviet Research in Boron Chemistry 1949-1956,
‘tEnglish Translation, Consultants Bureau, Inc,NY
BORON, ITS COMPOUNDS, EXPLOSIVES, FUELS (1956) 7)G.A.V.Boehm, Fortune(Dec 1957),166
AND PROPELLANTS 8)Sax(1957), 376-7 9)Experiment,Inc, “Combustion
Boron(Bor in Ger & Rus, Bore in Fr, Boro in Ital & of Elemental Boron”, TM i038(Feb thru April 1958)
Span), B, at wt 10.82; occurs in two forms: blk TM 1090(Aug thru Ott 1958) and TM 1094(Nov 1958~
monoclinic trysts & yel or brn amor powd; mp 204&r thru Jan 1959) 9a)H.Williams & W. A.Gey, USP
bp 3930°, d 2. 33(cryst), 1.73( amor); SO1 in nitric 29 00242(1959) & CA 53,22957(1959) (Use of B in
and sulfuric acids and in most molten metals; insol ignition compns) 10)W.E.Best, “Chemistry of Boron
in w, ale, ether & solns of caustic alkalies. The and Boron Compounds. A Literary Survey’, AEC,
element boron was isolated in 1808 by Gay-Lus sac TID 3523(1959) 1 l)USCongress, House Committee
& Thenard who reduced boron oxide(B203) with K on Science and Astronautics, “Boron High-Energy
by heating i t in an iron tube. Sir Humphrey Davey Fuels”, 86th Congress, First Session, Report No
independently obtd the same product and called 1191(1959) lIa)M. H. Crompton & J. E.~eed, ‘Some
the element “boron”. This element is not found Properties of High Energy Fuel Chemical Material%”
free in nature, but occurs in the form of berates Olin Mathieson(1959),p 12 12)F.A.Cotton,( ’Chem-
& boric acid. It can be prepd by the reduction of istry of Boron”, MIT Status Re ports No 1 to No 7
the oxide, borares or boron halides (1959) to 1961) 13)D.N.Williams, ”The Properties
Boron is one of a group of elements, such as Pb, of Boron”, Battelle Memorial Inst, DMIC Memo 41
Mn & As, which affects the central nervous system. (1960) (OTS PB No 161191) 14)J.A.Kohn, W.F.
It is a cumulative poison causing depression of Nye & G. K. Gau14, Edits, “Boron: Synthesis, Struc-
circulation, persistent vomiting & diarrhea, fol- ture and Propertie s“, PlenumPress,NY( 1960) (Pro-
lowed by profound shock and coma. Care should cee dings of Conference on Boron sponsored by
be observed in applying boron ointments & dres- US Army Signal CoqN Research and Development
sings over large areas of the body where the Laboratory, Sept 1959) 14a)H.Ellern, “hlodern
skin has been destroyed. It can be absorbed by Pyrotechnics”, ChemPubgCo,NY(196 1),281-3
the body in this way and by irrigation of body 15)W.Gerrard, “The Organic Chemistry of Boron”,
c a vities with solns contg boron. It is an expln AcademicPress,NY( 1961) 16)T).Lippmann & M.P.
hazard in the form of dust, which ignites” on Stoltenberg, “Hear Storage Materi a Is”, Lithium
contact with air (Ref 8) Corp, NY(June 1961),pp 34-7(B oron) 16b)R. F.
Boron is the only element in Group III that is Gould, Edit, “Borax to Boranes”, Advances in
nonmetallic in behavior. It is unaffected by air Chemistry Series No 32, A m erican ChemicaI
at RT but at higher temps it forms the nitride Society, Washington,DC( 196 1), 240pp 17)US
and the oxide(B20~ ). Boron reacts with F at RT hfilitary Specifications - not found in Dept of
amd with Cl, Br & S upon heating. It does not Defense ‘tIndex of Standards and Specifications,
react with H even when heated to red heat Supplement,Part l(Aug 1961)
Elemental boron is used chiefly in the metal
industry, such as a deoxidizer & degasifier and Boron, Estimation of. A general procedure has
for increasing the hardness of steels. Boron and been developed at PicArsn for estimating the
its compds are used as high energy fuels in expl boron content of organodecaborane compds. The
& proplnt compns. Uses of boron in blasting caps sample is refluxed in a mixt of perchloric & sulfu-
are listed in Refs 6a, 6b & 9b. An igniter compn ric acids with a small amt of K bichromate present
 B 252

to indicate completeness of digestion. After dilu- Its use in smoke-producing compns was patented
tion with water, an aliquot is made alkaline to by DeMent(Ref 20,pp 27-8)
litmus, then reacidifiecl and refluxed. The pH is Boron PentasuI/ide, B2S5; mw 181.97, wh trysts,
adjusted to 7.2 with Ba hydroxide, mannitol is mp 390°, d 1.85(Ref 14,P 378)
added and the vol of Ba hydroxide soIn required Boron Pbosphide, BP; mw 41.80, maroon powd, mp
to restore the pH to 7.2 is detd. The Ba hydroxide 200° (ignites) (Ref 14,p 378)
is standardized against boric acid in the present e Boron Triazide. See VOI l,p A525-L
of the digestion reagent. The method is of general Boron Tribromide(Boron Bromide), BBr3; mw 250.57
applicability, is relatively rapid and requires no COI fuming liq, fr p -45°, bp 91.7, d 2.650 at OO;
special apparatus or reagents vap press 40mm at 14° and 100mm at 33. 5°(Ref 14,
Refi R.M. Abbott, N. M. Liszt & M, Roth, “Estimation p 378-9)
of the Boron Content of Organodecaborane Com- Boron Trie~hyl(Boron EthyI or TriethyI Borine),
pounds”, Technical Note No F RL.TN~5, P icArsn, B(C2H~)3; mw 98.0, CO1 Iiq, fr p -93°, bp 95°, d
Dover,NY( 1961) 0.6961 at 23°; spontaneously flammable in air or
Note: It was recommended that this method be in- by them reaction with oxidizers(Ref 14,p 379) (See
cluded in US Specification MIL*STD*286 also Ref 18)
Boron Trimethyl(Boron Methyl or Trimethyl Borine)
Boron Azide. See Boron Triazide; Vol l,p A525-L B(CH3)3; mw 55.9, CO1 gas, fr p -161.5°, bp -20°,
d 1.91 g/Iiter(gas) and 0.625( soIid at -lOOO); high-
Boron Carbide. See Vol l,p A7 I-L ly dangerous when exposed to flame or by them
reaction with oxidizers; spontaneously flammable
Boron Compounds. The compds of boron exhibit, (Ref 14,p 380)
in general, the props of the compds of a non-metal. Boron Trioxide, See Boron Oxide
They indicate that the element is tervalent. The Boron Tris elenide, B2Se3; mw 258.52, yel gray
boron hy~ides(qv) seem to indicate the possibility powd(Ref 14,p 380)
of quadrivalency, although this question is not Boron Trisul{ide, B2S3; mw 117.84, wh trysts,
definitely settled(Ref 9) mp 310°, d 1.55(Ref 14,p 380)
The Univ of Delaware under Contract DA-36 Bohn(Ref 2) explains that the glowing of the
-034-ORD-2526RD has published a series of re- oxide of certain metals(such as Fe20~ & Cr20~)
ports on *Adducts of Boron Compounds’‘(Ref 15) when heated to dull redness, and the explosive
Some of the boron compds listed in the literature devitrification of certain ceglasses” such as
are as follows: CUB O Co2B20~ & MnB407 on heating to 700
Boron Bromide. See Boron Tribromide -900F, ~e caused by the transition frum amor to
Boron Bromide Diiodide, BBr12; mw 344.58, CO1 the tryst state(See also Refs 1,4,8,10,11 & 13
liq, bp 180°(Ref 14,p 376) for more detailed discussions)
Boron Bromide Pentabydride, B zH5Br; mw 106.60, Re/s: l)Mellor ~ 1924),23-149 2)J .Bohn,ZAnor~
CO1 gas, mp -104°, bp 10°(approx) (Ref 14,p376) Chem 149,217-22( 1925)& CA 20,527( 1926)
BororI Carbide. See VOI l,p A7 1-L and Ref 14,p 3)MeHor 8(1928), 108 4)Thorpe 2(1938 ),40-6
376. Its use in smoke-producing compns was 5)InorgSynth I( 1939),21-4(prepn of BF3 ) 6)R.J.
patented by DeMent(Ref 20,pp 26-7) Thomas et al,IEC 32,408-10( 1940)& CA 34,2343
Boron Chloride. See Boron Trichloride ( 1940) (Sulfonation & nitration reactions promoted
Boron Chloride Pentahydride, ~2H5Cl; mw 62.14, by BF3) 7)G.F.Hennion,USP 23142 12( 1943)&
col gas highly unstable, bp -78 at 18mm(Ref 14, CA 37,5077( 1943) (BF3, used to promote nitration)
p 376) 8)Hackh’s( 1944), 139-40 9)MeHor( 1946),658-63
Boron Dibromide Iodide, BBr21; mw 297.57, col 10)Kirk & Othmer 2( 1948),588-622 1 l)Partington
Iiq, bp 125°, vap d 10.3(Ref 14, p 377) (1950),652-59 lla)Groggins( 1952),p 32( Effect of
Boron Hydrides. See below, following Boron Fuels BF3 in nitration reactions) (Not found in 5th ed,
Boron Nitride, BN; mw 24.83, hex wh trysts, mp 1958) 12)F. J. Sowa,USP 260681 fi1952) & CA 46,
3000°(subl), d 2.20(Ref 14,378) (See also Refs 3 11090( 195 2) (Manuf of BN & metallic nitrides)
& 12 and Ref 20a,pp 41-4) 13)Gmelin, Syst Nr 13( 1954), 123-253 14)Sax
Boron Ojide(Boron Trioxide or Boric oxide) B *03; ( 1957),376-80 15 )Univ of DeIaware ~Adducts
mw 69.64, vitreous CO1 trysts, mp 450° (approx), of Boron Compounds” ,Quarterly Progress Rpts
bp 1500°, d 1.844(Ref 14,P 378) (See also Ref 1, 2nd through 15th(l Ott 1957 to 31 March 1961
p 39; Ref 18a,p 11; Ref 19 and Ref 20a,pp 30-3). 15a)J.Morel & R. Keck,MP 41 ,375-8(1959) (Prepn of
 B 253

some org B compds contg N) 16)A.V.Topchiev, 3)L,D.Jackson,USP 2796339(1957) & CA 51,

S. V. Zavgorodnii & Ya,M.P aushkin, “Boron Fluoride 13399( 1957) 4)C. L. Mader, “The Performance of
and Its Compounds as Catalysts in Organic Chem- Boron Explosives”, Univ of Calif,Los Alamos
istry” ,Pergamon Press,NY( 1959) (Translated SciLab,LA-2341( 1956) (Conf, not used as a source
from Russian by J. T. Greaves) 18) J. T. Maurel et of info) 5)A. F. Taschler & E. E. Jones,PA FRL
al, MP 41,375-8( 1959)( Organic derivs of boron) Tech Notes FRL-TN-3( 1960)
18a)M.Crompton & J. E. Reed, ‘Some Properties of
High Energy Fuel Chemical .Materials”, Olin Math- Boron Fuels. See Boron Hydride Fuels
ieson( 1959) 19)J .L. Wilding et al, ‘The Toxicity
of Boron Oxide”, Chemical Warfare Laboratories Boron Hydrides, Derivatives and Fuels
Report, CWLR 2334( lXO) 19a)Kirk & Othmer, Boron Hydrides(Boranes). These constitute
a
2nd Suppl( 1960), 109-26 20)J.DeMent,USP 2995526 group of compds which may be represented by
( 1961),pp 26-8 20a)D.Lippmann & M. P.Stoltenberg two generic formulas: BnHn + ~ and BnHn + ~
“Heat Storage Materials” ,Lithium Corp,NY(June
(Ref 3). The BnHn+ ~ series is the more stable
196 l),pp 34-7 for Boron
but all boranes are electron deficient molecules
and considerable work has been undertaken to
Boron Explosives. The use of amoi boron in expls
ascertain their structures, their generation
was studied by PhiIlips(Ref 1) at PicArsn as a
from diborne & theit subsequent interconversion.
component of “Boronite”( qv) expls developed by
The existence of some of these compds has been
the Goss Engineering Co of Seattle, Washington.
known since 1881. A comprehensive review of
It was concluded, at that time, that replacement
boranes may be found in many refs, such as 1,6,
of Al by B in military expls showed no advantages
8,9,10,11,12,16,18,19,21,29 & 31
over std expls. Boron has been used in the develop-
Sax(Ref 27) has discussed the toxicity, fire &
ment of some gasless delay fuze compns and in
expln hazards of boron hydrides. The max allow-
pyrotechnic mixts for flares & incendiary bombs
able concn(MAC) is O. lp per million in ak. These
(Ref 3). Werbel(Ref 2a) proposed Ba chromate/boron
compds are dangerous when exposed to heat or
95/5 mixt as delay compn & 90/10 mixt as an ig-
flame or by them reaction. Boron hydrides evolve
niter. Taschler & Jones(Ref 5) have detd the e-
hydrogen upon contact with moisture and can pro-
lectrostatic sensitivity of barium chromate/boron
pagate a flame rapidly enough to cause ex~ln. The
compns. The performance of boron expls is de-
toxicity & health hazards are discussed also by
scribed by Mader(Ref 4)
The expl compdl,ithiurn Borazide, LiB(N~)4, is Krackow(Ref 20), Rothberg et al(Ref 37) & F ein-
silver et al(Ref 38)
described under Boron Azide, Vol 1, P, A525-L
The following boranes are expl, especially if
Zwicky(Ref 2) of CalTech has reported that by
traces of water are present: Diborane(Boroethane
the use of expls contg B, Li, Mg, Al, or Si it is
or Boron Hydride), B2H6; mw 27.7, CO1 gas hav-
possible to attain energy values of 4-7kcal/cc
ing a sickly sweet odor, fr p -165.5°, bp -92.5°
(common expls & proplnts develop energies not
(expl on heating to higher temps) d 0.447 (Iiq
exceeding 3kc al/cc). According to Zwicky it is
at -112° ), 0.577( solid at -1830), vap press 224mm
necessary, however, that the expl reaction gen-
at - 112°(Ref 27,p 548-9). A classical method for
erate at least a mod amt of gas to provide energy
the prepn of diborane was developed by Schlesinger
transfer. This can be accomplished by addg gas
& Brown(Ref 15) and involves the reaction of
generating expl combinations or by incorporating
boron trifluoride etherate with lithium hydride:
the desirable elements chemically, rather that
physically, in the original expl, such as in the 6LiH + 2BF3.(C2H5)20 = B2H6 + 6LiF + 2(C2HS)~
reaction: Other methods of prepn are from Na borohydride by
2A1(BH4)3 + 6 02(liq) = Al= 03 + 3B209 + 12H2 reaction with a Lewis acid (ferric chloride, cupric
chloride or boron halides) or by electrolysis of
Projectiles with such expl systems could be use- active metal borohydride,s, using a suitable elec-
ful as artificial meteors since they would be lunT trode system and a suitable SOIV such as di-
inous in the high vacuums of interplanetary space (methoxyethyl)ether(Ref 32). Dark elec discharges
(Ref 2) (See also Boron Hydrides, Boronites, in a Berthelot ozonizator transform diborane into
Boron Solid Propellants & Borotorpex) a nonvolatile yel hydride, (BH)X, which hydrolyzes
Re/s: l)A.J.Phillips, PATR 1292(1943) 2)F.
in water to H9B04; with dil HN03 it forms brn
Zwicky,Experientia 10,326-8(1954) & CA ~,
trysts which explode on contact with coned HNOa
14209( 1954) 2a)B.Werbel,PATR 2244(1955)
 1

B 254

(Ref 5). The explosive oxidn of diborane is dis- 4). In addn to these methods the Grignard reaction
cussed by Roth & Bauer(Ref 25) (See also Ref 34a can be employed. For example, decaborane will
p 31-!9) react with a methyl Grignard and produce the
Tetraborarze(Borobutane), B4H ,.; mw 53.4, gas product expected or it will react with double
having a disagreeable odor, fr p -120°, bp 1$ Grignard reagents to produce a cyclic deriv(Ref
(expl on heating to higher temps} vap press 28). Metalloboranes can be prepd from metal a-
580mm at 6°; highly dangerous, as shock can malgams, as illustrated by the following reactions
shatter the compressed-gas container releasing (Ref 3):
toxic materials which react vigorously with oxidg B2H6 + NaHgx —+ Na2B2H6 + Hg
agents(Ref 27,p 1160). This and higher boranes B4H10+NaHgx ----- Na2B4H10+ Hg
result from the pyrolysis of diborane. Although the Aluminum Borolrydride, AIB~H1 ~; mw 71.53, liq,
mechanisms for these reactions are not completely fr p -64.5°, bp 44.5°, vap d 400mm; ignites sponta-
understood, it is known that the unstable tetra- neously in air(Ref 27,P 260). Brokaw et al(Ref 14)
borane(B4H1 ~) & pentaborane(B5H, , ) are formed reported that the oxidn of l-butene induced by alu-
along with the stable pentaborane(B~H9 )(Ref 35) minum borohydride was expl after an induction period.
(See also Ref 34a,p 111) Reaction with 1, 3-but adiene yielded immed expln
P entaborane, StabIe(Pentaborane Enneahydride), but normal butane(n-C4H1 o) gave no expln. See also
B5H9; mw 63.2, CO1 gas or liq, fr p -46.6°, bp Ref 34a,pp 2-5 and pp 66-7( Lithium Borohydride) &
0° at 66mm; explodes spontaneously in air; d 0.61 pp 101-7( Sodium Borohydride)
at 0°> vap press 66mm at 0°, vap d 2.2(Ref 27,p The structures of some ethylated derivs of perzta-
983-4) ( See also Ref 34a,pp 81-90 and Refs 38a & borane and decaborane are reported by Williams(Ref
39) 34). Stock & Pohland(Ref 2) reported the formation
P entaborane, Unstable(Dihydropent aborane), of complexes by the reaction of NH3 with boranes.
B5H11; mw 65.2, CO1 liq which turns yel on The structure & props of these boron hydride ammo-
standing, fr p -129°, bp 0° at 57mm; explodes niates were studied by Agronomov(Ref 7)
spontaneously in air(Ref 27,p 984)( See also In addn to their uses as high energy fuels(HEF),
‘Ref 34a,p 91) boron hydrides and their org derivs are useful as
Hexaborane(Boron Hydride or Hexaboro diesel oil additives, as polymerization catalysts
Decahydride), B6H1 o; mw 75.0, CO1 Iiq which and as cetane improvers presumably because they
turns yel on standing, fr p -65.1, bp 0° at 7mm increase the flame speed of fuel-air mixts. Many
(explodes on heating); d 0.69 at 0°, vap press other possible applications are suggested for the
7.2mm at 0°, vap d 2.6(Ref 27,p 750) metalloboranes and their derivs(Ref 36)
D ecaborane(Boron Hydride or De.caboron Tetra- Re/s: See under Boron Hydride Fuels
decahydride), B10H14; mw 122.3, CO1 ndls, mp
99.7°, bp 213°(explodes on heating in O at 100° Boron Hydride Fuels(Boranes). Since WWII many
and in air when heated to decompn), d 0.94( solid) articles on the chemistry and uses of boron & its
& 0.78(liq at 100° ), vap press 19mm at 100°(Ref compds as additives to fuels(gasoline), and of the
27,p 534). The heat capacity, heats of fusion & use of alkyl boranes, as the so-called “exotic” or
vaporization, vap press and entropy are reported high-energy fuels(HEF), have appeared in tech and
by Furukawa & Park(Ref 24) (See also Ref 34a, nontechnical journals & newspapers. In automobile
pp 25-30) fuels(gasoline) boron compds, such as alkyldi-
Boron Hydride Derivatives. Alkyl boranes can be hydroxyboranes, are added in relatively small amts
prepd by alkylation of key intermediates, of di- (Ref 22). In HEF for air-breathing jet & rocket
borane or of higher boranes. Alkylation of a engines, alkyl borane is the fuel itself and is not
borane will proceed more readily if a functional an additive. Both jet and rocket engines have fuel
group, such as a halogen or an active metal atom, requirements which are not the same as those for
is attached to the borane. For example, a halo- the internal combustion engine. Martin(Ref 35) has
borane may react with a metal alkyl to produce summarized these requirements as follows: a)high
an alkyI borane, or a metal polyhydropolyborate heat of combustion b)low vap press c)thermal sta-
may react with an alkyl halide to produce an alkyl bility d)high density e)high flame speed and f)phys-
borane(Ref 35). Boranes may be alkylated or ary- ical props which insure its safe handling during
lated with an unsaturated hydrocarbon(Ref 13). manuf, shipping & storage
Alkoxy derivs of boranes can be prepd by allowing According to hlartin(Ref 35), the US Dept Of
a borane to react with an appropriate alcohol(Ref Defense in 1952 made the them industry aware of
 its need for better HEF. No limitations were placed (Olin Mathieson Chem Corp) and ‘Hi-Cal”(Callery
with regard to which atoms, molecules or mixts Chem Co) have been produced in plants owned by
thereof might be used to synthesize an improved these companies and in plants operated under
HEF. At that time there were available the follow- contract for the US Dept of Defense. The Callery
ing fuels: Chem Co has a company-owned plant at Lawrence,
Kansas and a plant operated for the 12ept of Navy
Fuel BTU/lb at Muskogee, Oklahoma. The Olin Mathieson Chem
Liquid hydrogen 52470 Corp has a company-owned plant, a plant operated
Pentaborane(B5H9) 29$61 for the Dept of Navy, and a plant operated for the
JP-4(kerosene hydrocarbon) 18605 Dept of Air Force, all located at Niagra Falls ,NY
(Ref 35)
Liq hydrogen represents the ultimate attainable in a
Martin(Ref 35) has compared the pertinent props
fuel. However, its low density & low bp make its
of a typical HEF with those of JP-6(a special
use on a large scale difficult. Study of the periodic
~rade of kerosene for jet aircraft which are as fol-
table of the elements indicated that a better HEF
Iows:
could be prepd only if hydrogen, beryllium or boron
Properties JP< HEF
were used as ‘%uilding blocks”. Beryllium was
eliminated, according to Martin(Ref 35), because of Heating value, BTU/lb 18600 25000
its limited availability, extreme toxicity of its Specific gravity at 70° F 0.78 0.82
compds and because no liq complexes of Be are Flame speed 6-lox
known. Consequently boron & its hydrides were Chemically stable at ‘F 5$ 500
selected as the materials from which the synthesis
of a better HEF would be attempted These data indicate that borane fuels have many
Boehm(Ref 27a) reported that scientists at the props which are superior to those of JP-6. Com-
Lewis Flight Propulsion Labs of NACA began in parison of the performance of a borane fuel with
1946 to investigate some of the boranes synthe- that of JP type, and using liq O as oxidizer, shows
sized by GE & Aerojet-General Corp, Azuza, Calif. that a HE F increases the range of air-breathing
Soon thereafter the ONR became interested in engines or rockets by ca 50% over that obtd with
boranes and awarded contracts to several Iaboratories a JP fuel in tk s-e vehicle
which focused their attn on three basic compds: Boranes as fuels compare favorably with other
diborane (B2H6), a gas having Q= 32000; well established fuels in liq propellants(Ref
pentaborane (B5H9), a liq having Qc 30000; and 35) as shown in the following table:
decaborane (B ,OH ,4), a solid having Qc 28000 Liq Propellant Wt % Free Hz Specific Impulse
BTU/lb at STP sec (20 ata
The se were the three most common boranes known N2H4-F2 o 279
at that time. Because the Qc of each is high, it was N2H4-F2-H2 10 323
predicted that these boranes might be modified to 02-H2 16 354
convert them to liq compds, having the desired F2-H2 8 361
props, and without Iosing much of their energy con- B2H6-02-H2 12 363
tent. Tk ideal HEF ~olecule would contain there- 14
B#f9-Oz-H2 363
fore boron, as much hydrogen as possible & a third
element. After eliminating beryllium because of its This table also indicates the advantage of using
scarcity & toxicity the next best elements, from
hydrogen as a fuel in liquid proplnts. When only
the viewpoint of their Qc values, are lithium and 10% H is added to a hydrazine-fluorine system, the
carbon. Because hydrocarbons are fuels, it was
thrust(specific impuls@ is increased approx 15%.
decided to modify boranes by introducing a small Without hydrazine, the hydrogen-fluorine system
quantity of C into them. From a study of the
gives a further increase of approx 12!%. Proplnts
boron-hydrogen-carbon ternary system, areas were
contg boranes have higher specific impulse vahes
described representing compns or empirical
than are av a.ilabl e from well-known energetic sys-
formulas for the desired molecules(Ref 35). The
tems, such as 02-~ & F2-H2 systems (See also
syntheses of these molecules is classified and the
discussion by Clark Ref 17)
processes used cannot be described. For example,
A review of modern propInts for jet engines,
see Ref 33
particularly tk aluminum boro@dride(AIB~H, 2),
High-energy fuels under the trade names of ‘HEF” has been made by Orengo(Ref 23). See also the di~
 B 256

cussion by Sutton(Ref 26) and by Warren(Ref 30) L. Williams,ERDE Rpt No 12/R/59(1959) (Conf,
Re/s: l)Mellor 5( 1924),33-9 2)A.Stock & E. Poh- not used as a source of info) 34a)M.H.Crompton
land,Ber 59 B,221O-23(1926) & CA 21,541(1927) & J .E .Reed, ‘Some Properties of High Energy Fuel
3) A. Stock, “Hydrides of Boron and Silicones”, Chemical Materials”,Olin Alathieson( 1959) 3 5)D.R.
Cornell Univ Press,Ithaca,NY( 1933) 4)A.B.Burg Martin, ‘The Development of Borane Fuels’ ,JChem
& H. I. Schlesinger, JACS 55,4020(1933) 5)A.Stock Educ 36,208-14(1959) 36)Callery Chem Co, =Pro-
& W. Mathing,Ber 696,1456-75(1936) & CA 30,7056 duct Information Digest”, C&EN 37(May 1959)
-7( 1936) 6)Thorpe 2,(1938 ),40-3 7)L.E.Agronomov, 37)S.Rothberg et al, ”Toxicity and Personal Decon-
ZhObshchKhim 10, 1120-40( 1940)& CA 35,1333-35 tamination of Boron Hydride Propellant Fuels”,
( 1941) 8)H.I.Schlesinger & A. B. Burg,ChemRevs Chem’Warfare Labs,CWLR 2355( IY50) 37a)C.S.H
3i,l-41(1941) 9)S.H.Bauer,ChemRevs 31,43-75 Herrick et al,IEC 52, 105-12(1960) (Borane Pilot
19)Kirk & Othmer 2( 1948),593-600 1 l)H.J .Eme16us, Plants) 38)L.Feinsilver et al, ‘The Acute In-
AnalesRealSoc EspaiiFis y Qu;m Ser B44,675-88 halation Toxicity of Several Boron Hydride Fuels ~>
(1948) 12)R.P.BeH & H. J. Eme16us,QuartRev 2, Chem Warfare Labs Rpt CWLR 2367(1960)’(Conf,
132-5 1( 1948) 13)T.D.Hurd,JACS 70,2053(1948) not used as a source of info) 38a)NAAI,Rocket-
14)R.S.Brokaw et aI,JACS 72, 1793-5(1950)& CA dyneDiv,”P entaborane Handling Manual”. R*3 137
44,5686-7(1950) 15)H.I.Schlesinger & H. C. Brown, ( 1961) 39)CaHery Chem Co, “Physical Properties
USP 2543511(1951) 16)H.C.Brown,C&EN 29,5231 of Liquid Pentaboranes?( 1961) 40)Anon, ‘The Hand-
-3(1951) & CA 46,3437(1952) (A discussion of H.I. ling and Storage of Liquid Propellants”, Office of
Schlesinger’s researches on borohydrides) 17)J.D. the Director of Defense Research and Engineering?
Clark,Ordn 36,661-3(1952) & CA 48,11062(1952) Washington,DC( 196 1), 178-88 (Alkyl borane fuels)
(Rocket proplnt fuels such as B2H6, NH3 & N2H4 41)R.F.Gould,Edit, “Borax to Boranes”, Advances in
and oxidizers such as 02, H202 & HN09 are dis- Chemistry Series No 32 ,American Chemical Society,
cussed) 18)H.I.Schlesinger et al, JACS 75,186 Washington, DC(1961),240pp
(1953) & CA 47,3741-2(1953) 19)Ya.M.Paushkin,
UspekhiKhim 22,1114-37(1953) & CA 48,487(1954) Boronites. The GOSS Engineering Co of SeattIe,
Washington deveIoped several expls called
20)E. Krackow,ArchIndHygOccup mionalMed 8,335 “Boronite A“, Boronite B“ & Boronite C“. These
-9(1953) & CA 48,13947(1954) 21)Gmelin Syst Nr
were prepd by adding so-called amor boron to Amatol
13(1954),97-123 22)S.M.Darling,USP 2710251 & to make expls possibly suitable for military appli-
2(1955) 23) F. Orengo,Chimica(Milan) 11,55-7 cation’s
(1955) & CA 49,16383(1955) (A review of modern The compositions of the Boronites studied at
proplnts for jet engines, particululy the boro- PicArsn are as follows(Ref 2);
hydrides, such as A1B3H, z) 24)G.T.Furukawa &
R. P. Park, JRNBS 55,255-60(1955) (Research paper Composition Boronite A Boronite B B oronite C
No 2627) & CA 50, 11796(1956) 25)W.Roth & W.H. TNT 10 20 36
Bauer, “Combustion of Diborane-Oxygen Mixtures AN(Ammonium 83 75 62
at the Second Explosion Limit”, 5th Symposium on Nitrate)
Combustion, Reinhold, NY(195 5),pp 710-17;JPhChem Boron(amor ) 7 5 2
60,639-41(1956) & CA 50,13639(1956) 26)Sutton
(1956), 170 27)Sax( 1957),377-8 27a)G.A.W.Boehm Tests of these expls ,in comparison with TNT,
Fortune(Dec 1957), 166 27b)Kirk & Othmer,First 80/20 Amatol, Ammonal & Torpex, showed them to
Suppl( 1957),103-30(155 refs) (Boron hydrides) have approx the same sensitivity to impact as
28)B.Siegel et al,JACS 80,4523(1958) 29)W.N. Ammonal, but more sens than either 80/20
Lipscomb, “Recent Studies of the Boron Hydrides”, Amatol or TNT,and less sens than Torpex. The
Univ of Minnesota( 1958) (Contract DA-11-022-oRD bris ante values were less than those of Ammonal,
-1554) 30)Warren( 1958),22-4 3 l)J .Cueilleron, Torpex, TNT & 80/20 Amatol, except for Boronite
Chim&Ind(Paris) 80,553-60( 1958); reviewed in Ex- C, which gave a higher value than 80/20 Amatol.
plosivst 7, 152(1959) 32)R.M.Adams, “The Prep- Fragmentation tests also showed the Boronites
aration of Diborane” ,Paper No 29; “From Borax to to be inferior to TNT with regard to the number
Borane s“, Symposium, 133rd ACS Meeting, San of fragments produced. However, Ballistic Mortar
Francisco( 1958) 33)L.LBraddock, “Preparation Test showed all Boronites to be ca 20% stronger
of Boron Fuel Components”, Callery Chem Co than TNT, but inferior to Ammonal & Torpex
(1958) (Conf, not used as a source of info) 34)R. Doubt arose as to the purity of this ‘ ‘brown boron”
 B 257

since, from a theoretical viewpoint, the sub- Rpt PT~34(1945),p 22 2)L.C.Smith & E. H. Eyster,
stitution of boron for Al should result in the “Physical Testing of Explosives,Part III Miscel-
development of much higher temps in the propul- laneous Sensitivity Tests; Performance Tests=,
sive gases. An approx analysis of the brown boron OSRD Rpt 5746( 1945),PP 14,16 & 21 3)Anon,
was given by Goss Engineering Co as follows: “Summary Technical Report of Division $ NDRC’~
AIB , ~ 11, B70 50, B4H3 12, A1203 25, Fez03 0.5 VO1 l,Washington,DC( 1946),pp 39 & 45
& Si02 1.5%. It is apparent that this material was
not amor boron but a very impure oxide Boroxazolidines(Boroxazo Compounds). A study of
It was concluded that the “boron product” used the structures & reactivity of a series of borox-
above was of no value for use in AN/TNT expls azolidines, such as B, B-diphenylboroxazoIidine,
because of its deleterious effects on the stabiIity H2$-CH2-?
and brisance values of such mixts. AIso, it was H2N —------+ B(C6H~)2, has been reported by
concluded that the Boronite expls ‘A”, ‘{B* & “C” Weidmann & Zimmerman(Refs 1 & 2). The expl
offered no advantages over TNT or other std expls props of these boroxazo compds were not detd
now being used (Ref 2) Re/s: l)H.Weidmann & H. K. Zimmerman, Jr, Ann
Thorpe(Ref 1) defines boronite as a sulfide of 619,28-35( 1958) &620,4-7( 1959) 2)H.K.zimmerman
Cu & Fe, and of importance as an ore of CU(CU Jr & H. Weidmann et al, Texas A&M Res Founda-
45-71%). The exact compn of the mineral, boronite, tion Status Rept Nos 1 (1959), 2(1959), 3(1960),
has long been doubtful(Cu5FeS4 ) 4(1960), 5(1960), 6(1960), 7(1961) & 8(1961 )(OOR
Z2e/s: I)Thorpe 2(1938),32 2)A.J.PhilIips, *The Proj No 2359, Contract DA-23-072-ORD-1432)
Use of Amorphous Boron in Explosives”, PATR
1292(1943)
Bosch, 1874-1940). Ger scientist
Carl( who special-
Boron Oxide. See under Boron Compounds ized in the prepn of nitrogen-contg org compds and
collaborated with Haber in the synthesis of am-
Boron Solid Propellants, The investigation and use monia. Was director of IGFarbenindustries
of boron in solid proplnts are described in the fol- Re/s: I)C.Krauch,AngChem 53,285-8(1940) 2)P.
lowing classified repts MiiHer,SS 35, 123-4(1940)
Re/s: l)Rohm & Haas Co Rpt p~55*l S(Aug 1955)
(Conf) 2)Reaction Motors Inc Rpts o~~~ I & Bostaph’s Explosive. Contained KC104 37, DNB 11,
074*Q2( 1956) (Conf) 3)E.DeIaney & P. Lensi, NaN03 43, woodmeaI 8 & rosin 1%
Reaction Motors Inc 4th Quarterly Rpt(June 1957) Refl H. P. Bostaph,USP 1038275(1912) & CA 6,3524
(Conf) 4)E.Delaney & P. Lensi,Thiokol Chem (1912)
Corp, Reaction Motors Div Rpt FWW074F (1958
-59) (Final Ilpt on Contract NOrd 16895) (Conf) Bottelage des Poudres(Fr) (Trussing or Bundling
5)D. J. Mann, Thiokol Chem Corp,Reaction Motors of Propellants). In order to facilitate loading op-
Div Rpt AERL415539 (1959) (Conf) erations with proplnt chges for some guns and to
have chges with higher d than loose proplnt, the
Boron Triazide. See VOI l,p A5 25-L following method was developed in France:
A weighed quantity of loose strands of proplnt
Boron Trioxide. See under Boron Compounds was prepd at the proplnt plant in a bundle(fagot in
Fr). This was compressed by means of a special
Borotorpex. A castable HE mixt composed of RDX, hydraulic press, called ‘botteleuse hydraulique”,
TNT & boron. in various proportions. One compn of and tied by means of silk threads. The compressed
RDX/TNT/boron-46/44/ 10 has the following props: bundles were loaded in waterproof containers and
d 1.742, brisance by Plate Denting Test 127% TNT shipped in this condition to the place of ammo
detonation velocity 76oO m/see at d 1.74 and loading. As the wt of each bundle was known, the
power by Ballistic Mortar Test 129% TNT (Ref 3). gun chge could be prepd in the field without
Other formulations of Borotorpex and their power weighing, thus saving time
by Ballistic Mortar Tests are as follows(Ref 2,p 16): Re/s: l)Venin,Burlot & L6corch6 ( 1932),599
48.6/46 .4/5.0 127%, 47. ~/44.9/8.O 131%, 43.5/41.5/ 2)Pepin LehalIeur(1935),305
15.0 112% and 41/39/20 101% TNT
Refs: l)D.P.MacDougall & E. H. Eyster, *Prepara- Böttger, Rudolph(or Böttcher,R.) ( 1806- 1887). Ger
tion and Testing of Explosives*, NDRC Div 8 Interim professor at the Univ of Frankfort-am-Main; dis-
 I

B 258

covered guncotton independently of Schiinbein, but “Bouncing Betty” Mine. An antipersonnel mine of
later in the same year( 1846). He also invented the fragmentation rype which is activared by small
matches and contributed to the study of poisoning pressure(such as a man walking over the buried
of Pt calatysts device) causing an igniter to fire and initiate a
Note: The name is spelled Bottcher by Colver(Ref propellant chge. The proplnt shoots the fragmenta-
2)& Stettbacher(Ref 3) and Bottger by Marshall tion projectile from the ground and at the same
(Ref 1)& Davis(Ref 4) rime activates a time fuze. When the proj reaches
Re/.s: I)Marshall 1(1917),39 2)Colver(1918),2 a height several ft above the ground, the HE
3)Stettbacher( 1933),12 4)Davis(1943),249 chge detonates arid sprays steel fragments in all
directions
Bottles. Military slang for JATO. Also shop or Refs: l)Ohart( 1946),363 & 367 2)Cook( 1958),
trade language for containers of high-pressure air 18-21
or other gas used for auxiliary power in complete
missile power plant “Boundary” Diameter Precise detn of the velocities
Refi Rocket Encycl(1959),58 of deton in cylinders of cast TNT(Buxton rotating
-mirror camera) shows that the veI rises as the
Bouche(Fr). Muzzle(Art) diam is increased from a ‘boundary diam”, below
which there is no propagation, to a ‘limiting diam”
Bouche à feu(Fr). Gun; piece of artillery at which the deton vel reaches a max. The effect
of heavy confinement is to reduce the boundary
Bouchon(Fr). Fuze seat of projectile; tompion; and limiting diams; the max vel re mains unaltered
fuze-plug Re/: W.B .Cybulski et al, PrRoySoc 197A, 51-72
(1949) & CA 44, 1707-8(1950)
Bouchon d étonant(Fr). Primer plug(fuze)
Bourrage(Fr). Tamping or stemming
Boudineuse(Fr). An app for cartridging gelatin
dynamites Bourrelet(Fr). Rim(of a cartridge) or centering band
of a projectile. An accurately machined surface(of
Boulengê(Le),Chronograph. Employed in early diam S1 larger than the shell body) which rests on
methods for measuring the vel of deton of expls. the lands of the bore. Its function is to center the
A very long cylindrical column of expl was initiat- projectile in the bore and to guide it during its
ed at one end and the time for the explosion to travel through the bore. Generally, the bow-relet is
travel to the other end was recorded by Le located at the forward end of the she 11 body, but
Boulang6 Chronograph. It is still used to measure some large caliber projectile have front & rear
the muzzle vel of projectiles. This apparatus has bourrelets. The diffr between the diam of the
been replaced by the Mettagang Recorder, Method bourrelet and that of the bore of the weapon is
of Dautriche and the Optical & Electronic Chrono- known as the clearance. This value varies in a
graphs for measuring velocities of deton of expls new gun from 0.005” for smalI calibers to 0.02”
(See also Chronographs) for large calibers
Re/s: l)Brunswig,Props( 1926),422 2)Sukharevskii Refs: I)Anon, “Ammunition Inspection Guide”,
& Pershakov( 1932),211 3)Stettbacher(1933),55 TM 9~1904(1944),11 2)Ohatt( 1946),98 & 118
4)Pepin LehalIeur(1935), 101 5)Hayes(1938),85-7 3)Anon, “Artillery Ammunition”, TM 9-190 I (1~0),
6)Meyer( 1943),32 7)P6rez Ara( 1945),93 35 4)Anon, “Ammunition General”, TM 9-1900
(1956) 125
“Bouncing Betty” Flare (Trip Flare M48). A device
constructed Iike Bouncing Betty Mine(see below), Bow and Arrow. See under Arrow, Vol l,p A488-R
except that the fragmentation proj is replaced by and Arbalest or Crossbow, Vol 1,p A477-L
a flare which is projected upwards when a firing Addnl Refi W. L. Rogers, ArOrdn 15,334-40(1935)
device is activated by a slight pressure or pull. (The bow as a missile weapon)
The device is hidden under-ground or camouflaged,
and is intended to give warning of enemy marauders Bowden, F.P. and Yoffe,A.D., Authors of “Initiation
or infiltration by hostile troops and Growth of ‘Explosives in Liquids and Solids”,
Refi Ohart( 1946),308 Cambridge Univ Press( 1952), 104pp
 B 259

Bowen patented in 1883 the use of carbonized and Ger proplnt, invented by Giittler in 1889, consisting
pulverized lignite in lieu of charcoal in gunpowders of NC, nitrated derivs of sugar, gum or starch with
intended for use in cannon. The same inventor one of the nitrated aromatic hydrocarbons, such as
patented in 1886 the use of charcoal obtained by benzene, toluene, phenol or naphthalene. The prod
cubonization of corn or other cereals could be used alone or in admixt with nitrates,
Refi Dariiel(1902),80 chlorates, picrates or chromates
In England the plastom~nite mixt, consisting of
Box ovens. Cubbage & Simmons(Ref) have made NC, DNT & Ba(N03)2, was considered a smokeless
studies of industrial type box ovens and presented powd. Three types were manufd: JCP, BP & KMP
design data for top expln reliefs (the lowering of for sporting powds, carbines & military weapons,
excess pressure by venting). The pressure-time respectively
variation in an oven during an expln was found to The mixt of NC with 5 times its wt of DNT was
consists of two pressure peaks. Based on measure- prepd in the form of brn grains. It was used in
ments of the pressure developed by exphts of Germany for hunting purposes. The expl mixt of
manufd gas-air mixts in drying ovens, empirical Giittler was considered remarkably heat resistant
formulas were derived relating the oven vol, and, in official experiments at Bucharest, in 1893,
venting area & wt of relief to the pressure devel- gave exce Ilent results
oped by the most violent gas-air rnixt. Pressure Giittler, in 1897, proposed a modification of the
measurements were made also for several gases & compn by the addn of 0.5-10.0% resin(colophony
vapors other than manufd gas, but Cubbage & or rosin). The mass was granulated and obtd as
Simmons(Ref) recommend that the design of oven granules varying in color from It brn to dk brn
reliefs be based on the pressures developed by Refi Daniel(1902),82 & 634
manufd gas
R ef: P. A. Cabbage & W. A. Simmons, Gas CounciI, BPY. A cast double-base proplnt for gas generators
Research Commun GC23,46pp(1955) & CA 50, th%eloped at ABL. Its compn & props are given in
2948(1956) conf Propellant Manual SP lA/M2(1959), Unit NO 579

Boyd Powders. Between 1893 & 1896 Boyd of BR 152(Polvere) (Ital). A brn prismatic powd used
Birmingham, England, patented several expl in Ital 149 & 152mm cannons
compns: Refi Daniel(1902), 82
Blasting expls for use in mines: a)KN03 43.75,
sulfur 18.75, Fe or Ca oxide 12.50, Ba(N03)2 Br 431 (Polvere) (Ital). A brn prismatic powd em-
12.50, PA 6.25 & wood meal or wood dust 6.25%. ployed in 254, 343 & 43 lmm cannons by the Ital
This powd can be ignited by a miner’s fuse in a navy
manner similar to BkPdr; b)NaN03 39.95, sulfur Refi Daniel(1902),82
22.20, AmmP 11.10, (NH4)2Cr207 10.10, K2Cr207
5.55, turf dust 5.55 & Ca(OH)2 5.55%. The ingre- Bracket’s Sporting Powder. A smokeless powd,
dients were mixed with cotton oil and pressed formerly manufd in the USA, consisted of nitro-
into cartridges Iignin(sol) 3.1.43, nitrolignin(insol) 13.70, NsN03
Propellant- Furnelessite (smokeless)- contd the 19.76, humus 18.94, charred wood flour 13.22 &
same ingredients as blasting expl (a) but in dif- moisture 2.95%
ferent proportions Refi Daniel( 1902),82
RippIene - an improved compn contg the same in-
gredients as blasting expl (a) except up to 10% Braconnot,H. Fr scientist who was the first to
PA was added prep, in 1833, nitrostarch(NS) which he called
Refi Daniel( 1902),81-2 “xyloidine”. This was done by dissolving starch
in strong HN03 and pouring the viscous Iiq into w.
Boy’s Apparatus. A device for taking shadow Braconnot also nitrated sawdust, cotton & linen to
photographs of projectiles in flight products which he considered to be identical with
Refl Cranz, VOI 3(1927),264 the xyloidine from starch. These products contain-
ed only 5-6% N and were not suitable for military
B Powder. See B(Poudre), this volume purposes. The name xyloidine is now applied
generally to any prod made by dissolving a carbo-
BP (Pulver) (Called in Fr Plastoménite). An early hydrate in HNOa and pouring into w. In spite of
 B 260

the cheapness of starch as a raw material, it has previously dried at 40°, is closely packed into a
never replaced cotton; this is due to the relative decompn tube(two similar tubes are used in each
instability of NS and to the mechanical difficulties test) which is placed in a bath heated at constant
in nitrating and purifying it temp by boiling vapors(for a temp of 110° toluene;
Refs: l)Daniel(1902),82 & 453 2)Marshall 1(1917) for 115° toluene 3ps & xylene Ip; for 130° amyl
194 3)T.Urbarkki,MAF 13, 825-6(1934) 4)Davis ale). The tube is first evacuated and then sealed
(1943),245 off while under vacuum by means of a stop-cock.
The evacuated tube is heated for 6 hrs at the
Brain Powders. Mixts, patented in England in 1873, desired test temp. At the end of this time the
contg NG 40-78% with KCIO~ , KN03, sugar, cork stop-cock arrangement on the tube is connected
charcoal, wood meal, dextrin,etc added to a manometer which, upon opening the stop-cock,
ZZefi Daniel(1902),83 registers the press created by the gases evolved
from the decompn of NC during heating. The amt
Brakes(Weapons). Almost all towed artillery and of gas, as ml of NO, is calcd from the rnanometric
self-propelled weapons have parking and stopping reading
brakes; the light and smaller carriages have only For example, 2g of 13% N NC evolved ca 1.4ml
parking brakes. Stopping brakes are operated of gas when heated at 115° and 4.5ml at 130°;
from the prime mover to slow down or stop the 2g of 12%N NC when heated at 130° evolved ca
carriage as the prime mover slows down or stops. 5.8ml as measured under STP
Parking brakes are operated by hand-brake levers Refl J. S. S. Brame, JSCI 31,159-61(1912)
on the carriage and are used for parking the
weapon when coupled to or detached from the Bram’s Powder. A mixt of K nitrate, K chlorate,
prime mover charcoal & oak sawdust 60, saturated with NG
Refl Anon, “Fundamentals of Artillery Weapons”, 40%
TM 9~2305(1947), 126 17e/: CondChemDict( 1942), 288(not found in
later editions)
Brakes, Muzzle Short cylindrical extensions for
the muzzle of a cannon, having a number of baf- Bran(called Kleie in Ger & Son in Fr). The
fles on the inside, against which the gases, fol- husks or outer skin covering of grains of wheat,
lowing the projectile from the tube, strike. The rye etc which are separated from the ground grain
gases exert a forward force on the baffles that (flour or meal) by sifting or bolting. The separation
partially counteracts the rearward force of recoil of bran & starch from corn is described b“y Kawabe
and thereby reduces the force of recoil (Ref 3). Wheat bran contains starch 52, gluten 14.9,
Refs: 1)0. W. Strickland et al, ‘General Summary of fat 3.6, sugar 1, wood fiber 9.7, salts 5‘& water
Explosive Plants”, PB Rpt No 925)1945),83 13.8%. Its nitration with mixed nitric-sulfuric acids
2)TM 9~2305( 1947),10 & 54 produces an expl, resembling NC in its props. The
nitrated bran has been used in some dynamites: NG
Brakes, Recoil. Mechanisms which control the 30 to 60 & nitrated bran 70 to 30). See Forcite
recoil of weapons. The modern recoil brake is a Re/s: l)Gody( 1907),471 2)Kast-Metz( 1944), 336
hydraulic brake and consists of a piston which 3)T.Kawabe,JapP 3174( 1953)&CA 48,8570(1954)
moves in a cylinder filled with oil. The recoil
brake is attached to the weapon in either of two Brandeisl Powder. A mixt of KN03 16, sulfur 2&
ways: a) the cylinder is attached to the tube(gun sugar 3ps
barrel) and moves with it during recoil and counter- Refl Daniel(1902),83
recoil, while the piston is fixed to the carriage
b) the piston is attached to the tube and moves Brander, an obsolete name for a solid-proplnt
with it during recoil and counter recoil, while the rocket engine which was manufd by F .W.Sander
cylinder is fixed to the carriage. In either case, at Wassermiinde, Germany
when the tube recoils, there is relative motion betw Refi Rocket Encycl(1959),59
the piston and the cylinder and the operation in
both eases is fundamentally the same Brandt Mortars. Light-weight mortars designed,
Refl TM9*2305(1947),42 beginning in 1918, by the Edgar Brandt Co of
Paris. The first mortar was of 45-mm caliber and
Brame’s Stability Test. A 2-g sample of NC, was capable of throwing an appreciable chge to
 B 261

a range of 1>0 to 1100yds. The mortar consisted of & tin. Various copper-base alloys are described
a smooth-bore barrel, closed at one end and fitted in Hackh’s (Ref 1) & in US specs(Ref 3). Brass
with an interior firing pin, against which the pro- usually is yel in color, is harder and stronger than
jectile fell and was automatically fired, as in the copper, and is malleable & ductile. Its props vary
Stokes mortar. To the base of the mortar there was with its compn
attached a smaIl circular plate which rested upon A 70/30-Cu/Zn brass is used to make the car-
the ground and was held in place by a spike pro- tridge cases which contain the propelling chges
truding from the center. Projectiles were made of for fixed and semi-fixed artillery ammo
steel and provided with four vanes. Total lerrgth of Refs: l.)Hackh’s( 1944), 142 2)Merriam-Webster’s
the mortar was’ 28”, approx wt 8.81bs; wt of projec- (1951),327 3)USSpecifications: JAN-B-67(1)
tile w/fuze 1.21bs, wt of HE chge 0.21b; max pro- (Brass, cartridge, disks); MIL-B-50B(Brass, car-
pelling chge 62g & rate of fire 30-40 rounds/rein tridge: sheet, strip, plate, bar and disks); MIL-B-
A larger mortar was of 60mm caliber, total -15894 A(Brass; die castings); MIL43-13351(Brass
length 40”, approx wt N.sibs; wt of loaded projec- forgings, free machining); MIL-B-5697A(2XBrass
tile 2.81bs, wt of HE chge 0.41b, wt of propeHing laminated); MIL-B-13492(Brass, Ieaded; tubing,
chge 230g; range 150- 1350yds, rate of fire 30-35 seamless); MIL-B-994A(Bras s,naval, wrought);
rounds/rein. This mortar was similar in construction MIL-B- 11552(Brass powder for sintered pats)
to the 45-mm mortar except that it was provided and MIL-B-12128A( l)(Brass, sintered; structural
with 4 legs to hold it in position parts)
Re/s: l) ArmyOrdHdb, ‘History of Trench Warfare
Mat6riel”, Govt PrintingOfc, Washington, DC(1920), Brassage des poudres(Fr). Mixing or blending of
129-30 2)M.E .Melroy, “Examina tion of 47mm and proplnts. In order to obtain proplnts having uni-
60mm Brandt Mortar Ammunition”,PATR 892(1938) form ballistic props, they must be blended thor-
3 )V.R.Reed, ‘gExamination of 60mm Brandt Mortar oughly. Roche describes the method of mixing
Ammunition(Second Lot) HE & Practice Rounds “, p~wders as used by la P oudrerie de Bergerac
PATR 967(1939) 4)A.B .Schilling, “Examination Refi M. Roche,MP 31, 158-77(1924)
of Two Unfired 120mm HE Shell Complete Rounds
of Brandt Mortar Ammunition(French)” ,PATR Brassey’s Annuals. The US Armed Forces year
1823(195 1) (Conf) books which are published by W. Clowes & Sons
Lt d, London and Macmillan Co, New York. The
Brandt Projectiles. These are described in the book published in 1957, edited by H. G. Thursfield
following refs: et al, marked the 68th year of publication. These
Re/s: l)C.G.Scheibner, “Investigation of 25mm VOIS contain much interesting info, both tech &
Brandt Armor Piercing Projectile”, PATR 900 political in nature
(1938) 2)A.B .Schilling, “37mm Armor piercing
Projectile(Brandt)’ ,PATR 1003( ~940) 3)A.B. BRAZILIAN ARMAMENT. There is no info at OUK
Schilling, “Examination of Three Unfired 100mm disposal about current Brazil expls, ammo and
Fixed Rounds of French Gun Ammunition Comp- weapons plants. The material presented here is
rising One AP-T Round, One APC-T Round and obsolete, in part
One TP-T Round”, PATR 19 12( 1953)(Conf) Brazilian Explosive Plants
a) F2brica President Vargas at Piquette, S?io
Brank’s Powders. Van Brank p atented in 1890 a Paulo State. It is equipped to manuf NG, NC,
smokeless powd contg NC & wax, such as carnauba. BkPdr, single- and double- base proplnts, dyna-
The same inventor patented in 1891-2 the following mites, TNT, sulfuric & nitric acids, ether and
compns: probably RDX(Ref 5)
B~ustirzg expl: KC103 87 & resin 13%; Sporting b) Fiibrica de Estrela, at Vila Inhomerin, State
!Iowd KC103 70.5, boiled linseed oil 28.5 & PbO of Rio de Janeiro. It is equipped to manuf BkPdr,
1.0%; and Military rifle Powd Kcloa 59.9, dynamites, primers, fuses and probably RDX
KzCr207 34.5 & carnauba wax 6.0% C) Cornpanhia Nitro Quimica Brasileir& at S~o
!?e/s: l)Daniel( 1902),790 2)Perez Ara( 1945,213 Miguel, near S?io Paulo. It is equipped to manuf
NC, TNT and nitric & sulfuric acids
d) Cornpanbia Dinamites do Brasil, at Rio de
Brass. A coppe~base alloy contg an appreciable Janeiro. It is equipped to manuf dynamites,
~mt of Zn. Formerly, brass was art alloy of copper BkPdr and fuses
 B 262

e ) DuPont do Brasil SA Industrial Qur%icas out elastic waves will transmit deton imperfectly.
(Duperial). It is equipped to manuf NG, NC, The progressive breaking of valence bonds or deton
dynamites and nitric and sulfuric acids wave may be transmitted thru any material and
f) Private Plants at Rio de Janeiro: Sociedade may, therefore, be considered a universal phenom-
AnonYma E.@lsouos ‘Rupturitd’.. Companbia enon
National ExpIosivos ‘*Seguranca” and Companbia The primary detong expls are crystalline compds
Ex~Zosivos “Chea!dite”(Ref l,p 125) having multiple bonds, which are shown by Carl
Brazilian Weapons (Ref 2) ro be weaker than expl compds having
The following small- arms, used in Brazil, are single bonds. Compds having such bonds are in-
discussed by Smith(Ref 3): herently under a strain and have a ‘certain rigidit$!
1) 7mm Rifle M 1894, Mauser, very sl modification The inherent s tre.ined condition of the primary
of the Spanish Mauser M 1893; the principal mili- detong expls can be increased by the application
tary rifle until it was replaced by the M1904(Ref 2) of pressure from an outside source. The more
2) 7mm Rifle M1904, Mauser, manuf in Belgium, sudden the application of pressure the greater
formerly the principal military rifle; similar in de- the breaking effect. Even tough and plastic
sign to the Ger Gewehr 98 materials can be broken by extremely sudden
3) 7.92mm Ri/le, Mauser manufd in Ger impact. The expls which are trysts and have
multiple bonds are most susceptilbe to
4)0. 30-06 US Service Ri/le
5) 1 lmm(O.433”) Single-Shot Rifle, M1871, Spanish breaking and also to deton. The breaking force
Remington Breechloader; not in current use required for deton of insensitive expls can be re-
6) llmm Single-Shot Rifle, M1871, Complain, manufd liably supplied only by the deton of primary expl
in Belgium compds which produce an extremely sudden and
No information at our disposal on Brazilian intense impulse. The fact that different primary
Artillery Weapons detong compds will produce impulses of different
Pepin LehaHeur(Ref l,p 470) described Brazilian amplitude, frequency and intensity is offered as
pyrotechnics and Da Rota Lima(Ref 4) reviewed an explanation of the selected effectiveness of
the “characteristics and methods of testing modern initiators for different secondary expl compds
expls Re/s: l)L.R.Carl, JFrankInst 230,75-94,207-27 &
Re/s: l)Pepin Lehalleur(1935), 125 & 470 2)hl.M. 355-74(1940) & CA 34,6449 & 8283(1940) 2)L.R.
Johns on, Jr, ‘Rifles and Machine Guns”, W.hforrow, Carl, JFrankInst 235,553-75(1943) & CA 37,4900
NY(1944),73 3)W.H.B.Smith, ‘The NRA Book of & 6131(1943)
Small Arms”, Military Service Pub co, Harrisburg,
Pa, VOI 2, “Rifles’’(1952),125-6 4)G.daRocaLima, Breakup Pressure(Rocket or JATO). See under
RevBrasilOuim(Sao Paulo) 33,205-16(1952) & CA Burning Time of a Rocket(or J ATO) Motor
47,319(19%) 5)Maj W.H. Gross, Explosivst 1956,
169 Breech. The rear part of a cannon, or other firearm,
aft of the bore(qv)
Breadbasket Bomb. See under BOMBS Re/: Merriam-Webster’s( 1961),274

Breaking Theory of Detonation. Carl(Ref 1) defines Breechblock. The principal part of the breech
detonation as the progressive breaking of vaIence mechanism and is essentially a large heavy
bonds by distortions, transmitted as elastic waves piece which accurately closes or covers the back
which are maintained by the energy released by end of the barrel. The three general types are:
recombination of the initial products of deton. The a)Interrupred-screw type, called by Hayes slotted
theory proposed is based on the sensitiveness or -screw type(Ref 1) b) Eccentric- screw(Nordenfeld)
tendency of molecules to undergo them breakdown. type and c) Sliding-wedge typ e(See also Breech
According to Carl, the shattering effect of expls Mechanism)
does not depend on rate of deton but is largely de- Ref: l)Hayes(1938),212-18 2)Anon,’’FundamentaIs
pendent on the reactivity of the initial products of of Artillery Weapons*,TM 9.2305(1947), 11-17
deton. Materials which are easily detonated are
the truly elastic materials(crystals). Any state of Breechflash. See !3ackflash
matter or agency which tends to prevent distortion
of the molecule or crystal will also reduce sensi- Breech·loader. A firearm or an artillery weapon
tivity, therefore, all materials which tend to damp that is loaded at. the breech instead of at the
 B 263

muzzle(See also Breech-loading Weapon) the tabati;re. One of the most successful breech
-loaders of the 19th century was the Martin-Henri
Breech·loading(ad j). Receiving the chgeat the rifle used by the British for many years(Ref 2,pp
breech. The action or method of loading at the 102-5, 113 & 117). Other 19th century successful
breech breech-loaders were: Braendlin-Albini( Belg),
Refi Merriam-Webster’s( 196 1), 274 Mauser(Ger), Roberts(US), Chassepot(Fr) and
Berdanka(Rus)(Ref 2,pp 125-31 & 135)
Breech·loading Cannon. See under Breech-1 oading At present, breech-loading rifles are used in all
Weapon countries not only for military but also for sporting
purposes
Breech·loading Rifle. See under Breech-loading The early attempts to devise a bronze breech
Weapon -loading cannon were unsuccessful because the
backward pressure of the gas ultimately blew out
Breech·loading Weapon. A firearm or an artillery the breech-block or else the gas created sufficient
weapon that is loaded through the breech and not pressure against the walls of the barrel to burst it.
through the muzzle as was done in ancient weapons As forged-alloy steels were perfected, breech-load-
Attempts to introduce breech-loading firearms were ing became a more practical possibility; at the same
made as early as the 16th century when matchlock time steel hoops or outer tubes were shrunk onto
arms were in use. A sample of such an arm, dated the barrel to strengthen it, or, at a Iater date, wire
1537, is in the London Tower Museum. This and was wound around the barrel at high tension(Ref
other early breech-loaders were not successful 2,P 83)
due to the lack of good seal(Ref 4,p 11). Some According to EncyclBritannica(Ref 3,p 467),
breech-loaders were invented in the era of the flint- the first fairly successful breech-loading cannons
lock, eg, the Ital “Chamber Piece” of 1694(Ref 4, were those of Cavalli, Sardinian officer and of
p 20). The Amer flintlock Hall rifle patented in Baron Wahrendorff of Sweden(ca 1840). Still more
1811, may be considered as the first reasonably successful were the guns developed during the
successful breech-loader to be extensively used. ’60s and ’70s by C. Ragon de Bange(France),
Originally a flintlock, it was adapted to the per- Aflred Krupp(Germany), Freyre(Spain) and Broad-
cussion and rim-fire systems in later years. Hall well(US). By the end of the 19th century breech
(Ref 4,p 20) developed his rifle without being -loading cannons were perfected and only very
aware that similar systems were being experimented few improvements have been made since that
with in Europe, among others, by Pauly( 1808) & time. Howitzers are also breech-loading weapons.
( 1812), Degoubert( 1818), Robert ( 1830) and De- The only artillery weapons which are muzzle-loaded
mondion(1831) (Ref l,pp 96 & 101) are light mortars (See also Breech Mechanisms)
The European systems at that time were not Refs: l)W.W.Greener, “The Gun and Its Develop-
successful, however, until the appearance, ca ment”,Cassell,P etter,Galpin & Co, London(1885),
1836, of the so-called needle gun(Zundnadelgewehr 96-216 2)J.R.Newman,’’Tools of War”, Doubleday,
in Ger), invented by J. N.von Dreyse(Ref 2,p 43 & Doran & Co, New York( 1943),43-4 & 83 3)Encyclo
Ref 3,p 24). This gun used paper cartridges and, pedia Britannica 2( 1952),467 (under Artillery)
although it was rapid-firing(in comparison with 4)W.H.B.Smith, “Small Arms of the World” ,Military
muzzle-loaders ), its range was short. Real success Service, Publishing Co, Harrisburg, Pa(1960),12 & 20
with breech-loaders was achieved when paper car-
~ridges were replaced by those made of metal, as Breech Mechanism. The assembly at the rear of a
was done in the Brit breech-loader “Enfield”, gun which receives the round of ammo, inserts it
converted from an old muzzle-loader(Ref 2,p 44). into the chamber, fires the round by detong the
2ther early successful breech-loaders were: primer and extracts the empty case(Refs 1,4 & 5).
Norwegian carbine(1842), Karl d’Abezz rifle Breech mechanisms may be divided into: a~arrier
Swiss) (1851), Mousqueton de Cent Gardes(Fr) -type and b)Tray-type operating mechanisms(Ref
1860) and Westley-Richards rifle(adopted in 1861 3,p 17)
Jy the Brit cavalry). In 1865, Snider invented a Safety devices, to prevent accidental firing or
ievice which permitted conversion of the Brit firing before the breech is closed, are normally
Znfield muzzle-loaders into breech-loaders. ‘The found on the breech mechanism. These devices
~rench also converted their muzzle- loaders with consist of levers or latches which function auto-
1 modification of the Snider device and called it matically. Detailed description of breech mecha-
 1

B 264

nisms are given in Refs 2 & 3. The Bofors rapid which is attached across the terminals of insulated
-fire breech mechanism is described in Ref 2,pp leg wires. This device constitutes the elec firing
218-19 element in an elec blasting cap(qv). Upon applica-
Re/.s: l)M.B .Garber, “A Modern Military Dictionary’: tion of elec current, the bridge heats to incandes-
Garber,Washington, DC( 1936),49 2)Hayes( 1938) cence and fires the ignition chge in the cap(Ref 4)
212-40 3)Anon, “Fundamentals of Artillery Weapons; Piccard(Ref 1) patented a bridge wire for blast-
TM 9.2305 ( 1947), 11-41 4)Glossary of 0rd(1959) ing caps. It consisted of gold ca 58.4 & nickel ca
49 5)Merriam-Webster’ s(1961), 274 41.6% alloyed together and drawn to the req size
to have a desired elec resistance per unit length.
Breech Obturation. A device that will prevent powd Bremer(Ref 2) patented a bridge wire alloy which
gases from passing to the rear into threads and consisted of rhodium, ruthenium and platinum in
other parts of the breech mechanism. In guns that the proportions of 2-.257o rhodium, 2-25% ruthenium
use fixed or semi-fixed ammo, the obturation and the balance platinum. Nash(Ref 3) patented an
is performed by the cartridge case, which expands elec firing device which includes in combination, a
under pressure in the bore to form a tight seal casing, an expl chge and a firing assembly adjacent
against the walls of the gun. In weapons using to the chge. The firing assembly consisted of a
separate-loading ammo, a device must be included pair of leg wires disposed in spaced relationship
in the breech mechanism. For this purpose, the to each other and connected to a bridge wire. The
Debange Obturator is used exclusively in US bridge wire is made of zirconium and has a metallic
weapons oxide adhering to the wire whereby the bridge wire
Re/.s: I)Hayes( 1938),224 2)TM 9-2305(1947),35 is caused to be pyrophorized under a relatively
low elec potential during a relatively short time
Breech Piece. The jacket of a heavy gun. In the Re/s: l)J.Piccard,USP 1926213(1933) 2)B.
later Krupp gun, “it receives the breechblock(qv) Bremer,USP 2080110(1937) 3)H.E.Nash,USP
and relieves the central tube of longitudinal 2320880( 1943) 4)Blasters’ Hdb( 1952),93-4
stress
Refl Merriam-Webster’ S( 195 1),332 Bridge Wire Lag. When an elec current passes.
through a bridge wire of devices such as elec
Breech Screw. In muzzle-loading muskets and detonators or blasting caps, there is a certain
rifles, a solid screw plug closing the bottom of interval(lapse of time) between the application
the bore of current and the bre aking(fusion) of the bridge
Refi Merriam-Webster’s( 1951),332 wire. This period of time is called “bridge wire
lag”
Breech Sight. The rear sight of a gun, usually This phenomenon is dependent upon the firing
mounted near the breech current used since the bridge wire will fuse in
Re/: Garber( 1936),49 a short time at higher amperage than at lower
~Ps. For many practical purposes, bridge wire
Bren Machine A light machine gun, widely
Gun. lag is not significant since in seismographic explns
used in WWII, developed in Czechoslovakia and and other types of work requiring fast caps, the
designed for infantry use. It was adopted as a instant the bridge wire breaks or fuses can be
std weapon by GtIlrit & other countries assumed to be the instant of deton. A far more
Re/.s: l) M. B. Garber,“A Modern Military Dictionary’”, serious factor affecting the overall time lag is
Garber,NY(1936),50 2)W.W.Holler, Edit, “Glossary the interval of time between the breaking of the
of Ordnance Terms”,OEHO( 1959),49 bridge wire and the actual deton of the cap.
This lag, c ailed ‘induction periods, depends to a
Brenzcatechin or Brenzöl(Ger). See Pyrocatecol certain extent upon the firing circuit used. For
example, at high amperages, such as 20amps,
Bresin Resin(Bresinharz in Ger). A raw material the bridge wire lag for a given ign compn will be
for NC lacquers & synthetic materials, described shorter and consequently the induction period will
in Refs 1 & 2 usually be longer than at lower amperages, such
l?e/.s: l)W.Schmandt,NC 7,5-7(1936) 2)W.Delaney, as 5 amps. At a given amperage, however, the
NC 7,219-20( 1936) induction period is a definite characteristic prop-
erty of the ign compn employed. Thus, certain
Bridge Wire. A small diam corrosion-resistant wire ign materials have an inherently long induction
 B 265

period under “Brisance-Detonation Velocity Relationship”)

The use of very fast ign agents involves, in Brisance may also be calcd from the formula of
most cases, considerable danger from the hazard Kast(see below) or determined experimentally by
of static elecy. It has been found that ign compds one of the methods listed under ‘Brisance, Experi-
which have a negligible induction period(or so mental Determinations”
-called fast compds) are susceptible to initiation Since brisance is approx proportional to deton-
by static elecy. Particularly susceptible to ation velocity, “force” and density of loading,
static elecy is Cu acetylide Kast proposed to determine it by the following
Refi W.H.Aughey, L. A. Burtows & W. E. Lawson, equation:
USP 2086527(1937)& CA 31,6466(1937) B = f x d x D, where B is brisance value
(Brisanzwert in Ger), d is density of charge,
Brigg’s Explosive. K chlorate 65.5, MNB 20.5 & D detonation velocity in m/see and f “specific
BkPdr 14.0% energy or force”, also called “specific pressures
Re/s: l) F. H. Briggs,USP 934990(1909) 2)Colver and in Fr ‘force sp;cifique de Sarrau”. The
(1919),673 Germans call it “spezifische Kraft oder Energie”.
The force is expressed in kg/cm2 and is equal to
Brimstone. The coml name for crude sulfur P. x V. x T/273, where P. is atmospheric pres-
R e/s: l)Hackh’s (1944), 143 2)Merriam-Webster’s sure expressed as 1.033kg/cm2, V. volume of
(1951),337 gases developed on expIn in cc per g of expl re-
duced to O°C and 760mm Hg pressure and T is
Brine. Water which is neady saturated with saIts, the max absolute temp of expln. On substituting
such as NaCl for f, in the above expression, the following
Re/: Hackh’s(1944),143 equation is obtained: B = p. x V. x T/273 x d x D
In the above equation T is equal to t+273 or to
Briner Method of Ozonization of Organic Compounds. Qe/c + 273 where Qe is the heat of expln in cal/g
See under Ozonization of Organic Compounds and c is the mean specific heat of the products of
expln in cal/g
BRISANCE OR SHATTERING EFFECT(Brisace As an example, for blasting gelat@(NG 92 & NC
in Fr, Brisanz in Ger, Brizantnost’ in Rus, 8%)jStettbacher( Ref 10,p 49) gives: p. = 1.033,
Dirompenza in Ital, Poder rompedor in Span) V. = 711.4cc per g, t = 4410°C, d 1.60 and D .
When an explosive detonates, tremendous pres- 7500m/sec. This gives:
sure is released practically instantaneously in a
shock wave which exists only a fraction of a second B= 1.033x 711.4 x”~x 1.6x 7500= 151.2x 106
at any given place. The subsequent expansion of Kast’s values for many expls are given in Refs
gases performs work but the sudden pressure l,2,3,4,5,5a,6,7,8,9,10,11,13,14,15’& 17. They are
thus created will shatter rather than displace listed in the appended table in conjunction with
any object in its path. The ability of an expl to detonation velocities and bris ante values deter-
demolish(fragment, shatter) a solid object (such mined experimentally by several methods
as steel, concrete, stone) when fired in direct evolved on deton and D the detonation velocity.
contact with it or in its vicinity is called brisance However, practical tests do not confirm the idea
(from the French ‘briser” = to break or shatter). that B is proportional to the square of the deton
From a military viewpoint brisance is of practical velocity but that simple proportionality (as in the
importance because it determines the effectiveness formula of Kast) agrees better with the facts(see
of an explosive in fragmenting shells, bomb Ref 2,p 476). Friederich(Ref 10a) introduced the
casings, grenades, mines, etc and in imparting term “specific brisance” and proposed to talc it
high velocities to the resuIting fragments. As the from the formula (D2max x A)/100 kg/cm2, where
shattering effect is dependent upon the suddenness D m= is maximum detonation velocity and A specific
with which the gaseous products of an expl are gravity in g/cc. The following table compares
liberated, the velocity of detonation is at least a ‘specific brisance w with Kast’s brisance values:
major factor in determining .brisance. It has been
found that there is a general linear relationship
between velocity of detonation and brisance, and See Table on Next Page
if the velocity is known it is possible to calculate
the brisance or vice versa(as will be shown below
 B 266

Explosive Kast’s B Specific B, Max Deton P2 = 0.00987 p, D2/4 where p, is the original
Value kg/cm2 Vel,m/sec density and D the detonation velocity in m/see.
A more accurate equation is also given by Cook
TNT 86.2x 106 862000 7200
(Ref 29,P 35)
PA 107.4X 106 1034000 7650
Lothrop & Handrick in an article(Ref 26a) dis-
Tetryl 1 14.9X 106 1117000 8050
cussing the relationship between performance and
PETN 183.7x 10s 1286000 8>25
constitution of pure organic compounds included
It should be noted that brisance is a vetycompli- curves showing the relationship between power &
cated phenomenon and that none of the existing brisance and oxygen balance of many organic ex-
methods of calcn, such as by Kast’s formula(see plosives
above), Herlin’s formula(Refs la & 12), Bichel’s Price(Ref 3 1), in discussing the dependence of
formula, Friederich’s formuIa(Ref 10a), etc or of damage effects upon detonation parameters of
experimental determinations gives exact interpre- organic high explosives, substituted the term
tation of B. The matter of detg it is complicated de tonat i,on pressure for bris anc e and detonation
by the fact that the B of a cartridge of expl is energy for power. She also stated that from data
different in different directions: if a cylindrical obtained at NOL, it has been possible to show
cartridge is detonated from one end, the action in that fragment velocity, shaped charge penetration,
the direction in which deton proceeds is considerably airblast, and underwater effects are related to the
greater than that in the opposite direction explosive properties of detonation pressure and
According to Cook(Ref 29,p 34) the term brisance detonation energy. For more info on this subject
was used to describe the property now attributed see Ref 31
to detonation pressure. This property may in many A table giving Brisance, by various methods,
cases be calculated from fundamental physical as well as Detonation Velocity and Power pre-
laws cedes Refs (See also Brisance-Detonation
For a condensed explosive the detonation pres- Velocity Relationship, which follows Refs)
sure p2 maY be approx calcd from the equation:

Table I

Comparison of Brisance Values Calculated by I@s#s Formula, Relative Brisance Values Obtained by Various
Experimental Procedures; Detonation Velocities and Power Determined by Various Methods for Principal Explosives

ExpIosive Brisance Brisance Power

by Kast Relative Density Method Relative Density D eton Density Method Relative
of %TNT d Velocity d of % TNT
(. ?06) ‘m g;cc Detg g/cc m/see g/cc Detg
Abel(or Pictic) Powder — — 3500 – EMIT 75
(Brit)(KN03 57& (See also Vol l,p Al-R) (Ref 24,p 104)
AmmP 43%)
Aldorfit(AN 81, TNT 17 CCCT ca 65 1.05 4500 1.05 TT 129
& woodmeal 2%)

Alumatol(AN 77,TNT 20 Expl characteristics SI higher than those for Amatol 80/2?3
& Al 3%) (See also Vol l,p A14LR)

Amarex 9(AN 50,TNT 41 l?xpl characteristics higher than for Arnatol 60/40
& RDX 9.) (See also Vol l,p 157-R) (Ref 24,p 133)

Abbreviations: BMT-BaII istic Mortar Test; BPT-BaHistic Pendulum Test; CCCT-Copper Cylinder
Compression Test; FET-Fragmentation Efficiency Test; FGT-Fragment Gun Tesq LBCT-L e ad Block
Compression Test; PCT-Plate Cutting Test; PDT-Plate Denting Tesq $T-Sand Test and TT-Trauxl Test
(Lead Block Expansion Test)
Notes: Most Sand Test values listed in this table were detd for 0.4g samples compressed at 3000 or
34@si. Their densities were not determined except in a few cases
 ----
B 267

Explosive Brisance Brisance Power-.

by Kast -Relative Density Method Relative Density Deton Density Method Relative
%TNT d %TNT d Velocity d of
(x :06) g/cc ::g g/cc M/see - g/cc Detg

Anmtol ~/2wAN 80 & m 74 5300 1.6 TT 126

TNT 20%) BMT 130

AInatol 60/4qAN 60 & ST 90 6200 1.6 BMT 128

TNT 40%) FET 81 1.53

Amatol 50/5@AN 50& ST 90 64OO 1.59 BMT 123

TNT 50%) FET 82 1.55 TT 116

Amatol 40/60(AN 40 & 77.1 89 1.56 ST 94 655o 1.6 TT 120

TNT 60%) CCCT 81 1.56

5-Aminotetrazole TT 117
Nitrate (See also Vol l,p 259-R)

Ammonal(Austrisn) 85.5 99 1.60 CCCT 78 1.60

(AN 46,TNT 30,AI 22
& brown coal 2%)

Ammonal(Brit)(AN 65, ST 47 3300 1.6 BMT 122

TNT 15,A1 10 or 17 & (Ref 24,pp 854)
ch srcoal 10 or 3%)

Ammonal(us)(AN 22, ST 100 — ?3hff 122

TNT 67 & Al 11%) FET 108 L42

Ammonium Cre sylite See Ek rasit

Arrunonium Methylenedi- - - - - B~ 142

nitramine

Ammonium Nitrate(AN) No expln 2800 1.0 TT 75

[See also Vol 1,pp A321-L, A~21(tab~”~d A32~~] LBs~ 55 1.3 Bhm 79

Ammonium Nitrate/Al - – – - BMT 136

/TNT-81/ 10/9

Ammonium Nitrate — — Bhff 135

/EDNA/TNT-@/20/20 -

Ammonium Nitroform - - - - — — TT 128

Ammonium Perchlorate 17 19.7 1.2 ST No expln 3000 1.3 Bhm lm

30.6 35.8 1.3

Ammonium Picrste(AmrnP) - - - ST 84-7 - 7000 1.6 BM 9s99

(Explosive D or Dunnite) PDT 91 1.50
FET 96 1.53
See page B 266 for the meaning of Abbreviations
 1

B 268

Explosive Brisance Brisance Power

by Kast Relative Density Method Relative Density Deton Density Method Relative
%TNT d of %TNT d Velocity d of %TNT
(x !06) g/cc Detg g/cc m/see g/cc Detg
Ammonium Trinitrocresy- Expl characteristics are lower than those of PA
late/Potassium Nitrate Note: According to Pepin-Lehalleur( Ref 14,p 374) this mixt is Austrian military expl
Ecrasite but Stettbacher(Ref 27a,p 77) claimed that Austrian Ekrasit
consisted of PA with small amts of DNN or DNB

Anh ydroenneaheptitol Brisance > PETN Bhff 134-7

Pentanitrate

Azidoethylnitrate — — 6550 1.34 TT 161-70

Azidohydroxytetrazole — — — — — TT 89

Baratol(Ba nitrate — — ST 56 – – — —
67& TNT 33% ) PDT 61 2.52

Baratol(Ba nitrate 10 — — ST 84 - 5900 1.65 TT 98

& TNT 90%) BMT 98

Baronal(Ba nitrnte 50, — — ST 83 – 5450 2.32 BMT 90-96

TNT 35 & Al 15%)

Benzenehexametha noI Its expl characteristics are given in classified

Hexanitrate .4.D. Little,Inc Reports

Bis(2, 2 ,2-trinitroethyl) See Di(2,2,2-trinirroethyl)-nitramine

-nitramine(BTNEU or HOX)

Bis(2, 2, 2-trinitroethyl) See Di(2,2, 2-trinitroethyl)-urea

-urea(13 TNEU)

Black Powcler(K nitrate – - – ST 22 – 400 1.6 TT 10

75,ch ~COd 15 & Sldfut BMT 45
lo%)

Blasting Gelatin 156.3 182 1.63 PDT 113 1.55 8000 1.55 TT 194
(NG 92 & NC 8%) 151.2 176 1.60 CCCT 133 1.63

Blasting Gelatin with - - - - - – 7000 1.9 –

31% Al

Bo ronite B(AN 75, — ST 82.5 – – — BMT 118

TNT 20& boron 5%) FET 85 1.35

Boroto rpex(RDY 46, TNT - – - PDT 127 1.74 7600 1.74 BMT 129
44& boron 10%)

Bsx See 1,7-Diaceto xytetramethylene-2,4,6-trinitramine

See page B 266 for the meaning of Abbreviations

 B 269

Explosive Brisance Brisance Power

by Kast Relative Density Method Relative Density Deton Density Method Relative
%TNT d of %TNT d Velocity d of % TNT
(x !06) g/cc Detg g/cc m/see g/cc Detg

BThi(TetryI 55,TNT 25 - - - FET 107 1.77 – – – -

&AI 20%)

BTNEN Abbreviation of Bis(2,2,2-trinitroe~yI)-nitramine

It is listed in this table as Di(2,2,2-trinitroethyl)-nittamine

BTNEU Abbreviation of Bis(2,2,2-trinitroeth~l)-urea. It is listed in this table as

I?i(2,2,2-trinitroethyl ~tiea -

Burtowite(Brit)(AN 74, Expl characteristics comparable to Ammonal(~)

TNT 16& A1,,1OZ)

1,2,3-Butanetriol Trinitrate - - - ST 112 1.5 -

1,2,4-Bupetiiol Trinirrate - - - ST 101 1.52 - BMT 140

Butyleneglycol Dinitrate - - - — — TT 13@50

CE (Brit) See Tetryl

Cheddite(KC103 79,DNT 37.6 44 1.3 CCCT 48-64 1.3 3000 1.3 TT S92
15, castor oil 5 &MNN 1%)

Composition A(or A-3) - ST 107-15 - 8200 1.6o TT 144

(RDX 91 & wax 9%) PDT 126 1.61 BMT 132-5
FET 150 1.63

Composition A, Aluminized - PDT 110 1.72 7800 1.70 BMT 142

(RDX 73,Al 18& wax 8%)

Composition B(RDX 60 & - ST 112-21 – 7790 1.68 131

TNT 40% with 1% Wax PDT 129-32 1.66-1.72 134
added) FET 139 1.65

Composition C(US~PE-2 - ST 108 - 7400 1.50 TT 126

(Brit)(RDX 88.3 &non-expl PDT 112 1.58 BMT 125
oil contg O.6 lecithin
11.7%)

Composition C-2(RDX - ST 99 - 7800 1.57 BMT

78.7, TNT 5.O,DNT 12.7; PDT 111 1.52
MNT 2.7,NC 0.6 & solvent
1%)

Composition C-3( RDX77, - ST 112 - 7625 1.60 TT 117

Tettyl 3, TNT4,DNT 10, PDT 11418 1.57 BMT 126
MNT 5 &NC 1%) FET 133 1.59

See page B 266 for the meaning of Abbreviations

 I

B 270

Explosive Brisance Brisance Power

by Kast Relative Density Method Relative Density Deton Density Method Relative
%TNT d-of %TNT d Velocity d of %TNT
(x !06) g/cc Detg g/cc rn/sec g/cc Detg

Composition C~ [R DX91, - - – ST 116 — 8040 1.59 Bkm 130

polyisobutylene 2. l,motor PDT 115-30 1.60
oil 1.6 & di(2-ethyl) seba-
cate 5.3%)1

Copper Chlorotetrazole s-r 53 —

Ctesylite (Kresilit) See Trinitrocresol

Cyanuric Triazide 70.7 82 1.20 ST 99 7500 1.54 TT 140-5

122 142 1.54 Bhff 145

Cyclofive (RDX 53 & PDT 124 cast — BMT 134

Fivonite47%)

Cyclonite See Cyclotrimethylenetrinitramine

Cyclotetramethylene- — — ST 125-55 9124 1.84 TT 159-65

tetranitrsmine (HMX) BIbm 150
(beta) BPT 170

Cyclotol 75/25(RDX — ST 130 8035 1.70 Bhm 137

75& TNT25%)

Cyclotol 70/3@lDX ST 128 8C60 1.72 BMT 135

70& TNT 30%) PDT 136 1.72 TT 145
FET 163 1.71

Cyclotol 65/35 (R DX — — ST 126 — 7974 1.72 BMT 133

65& TNT 35%)

CycIotol 60/40 (RDX — ST 125 7900 1.72 BMT 130

60& TNr 40%) PDT 132 1.72

Cyclotol 55/45 (RDx — . — BIWT 127

55& TNT45%)

Cyclotol 40/60 (RDx — — 7485 1.68 BMT 123

40& TNT 60%)

Cyclotol 30/70(RDx — ST 112 — Bh4T 115

3082 TNT 70%)

Cyclotrimethylenetri- 188 218 1.70 ST 140 8270 1.675 TT 170

nitramine (Cyclonite, CCCT 144 1.70 BMT 150
RIM or Hexogene) PCT 125 1.70
PDT 135-41 1.71

See page B 266 for the meaning of Abbreviations

 B 271

Explosive Brisance Brisance Power

by Kast Relative Density Method Relative Density Deton Density Metlhod Relative
%TNT d Velocity d of % TNT
(x !06) ‘m g}cc D;;g g/cc dsec g/cc Detg

Cyclotrimethylenetri- ST 102-18 - 7300 - TT 122-6

nitrosoamine or R-Salt 7000 1.42 BMT 134
(Ger R-Salz)
Note: other expl characteristics are given in Ref 30a,p 354(Conf)
[See ako PATR 2510( 1958),p Ger 17qR-Salz) and OSRD 2014(Iw~

DBX (Depth Bomb E x- ST 121 - 6800 1.68 BMT 146

plosive)(RDX21, AN21, PDT 102 1.76
TNT40&Al 18%)

Dentex(RDX 48,DNT 34 Expl characteristics not found was developed as a substitute for Torpex-2
& Al lWO) (Ref 24b,p 33)

l,7-Diacetoxytetta- TT 85
methylene-2,4,6-tri- BMT 120
nirramine

Disminotrinitro- See Ref 30a,p 361(Conf)

benzene

Diamdinitrophenol ST 97-104 7100 1.63 TT 105-10

(DADNPh) LBCT 71

Dietha nolnitramine ST 71 7800 1.6 TT 160

lXnitrate(DINA) PDT 119 1.50 BMT 140-58

Diethyleneglycold i- ST 95 1.38 6800 1.38 TT 134-58

nirrate (DEGDN) BMT 127-37

Diethyleneglyco ld i- ST 165 1.5

nitrate/Nitrog 1ycerin
-50/50

2,6-Dimethylol-2,6-di- BMT 138

nitro-1,7-hep tanediol
Tetranirrate

2,5-Dimerhylol-2,5 BMT 147

-dinitro- 1,6-hexsnediol
Tetranitrate

DINA See Diethsnolnitraminedinittate

Dinitraminoisopro pyl- — BMT 142

nitrate

1,3-Dinitramirto-2-prop- — BMT 142

anol Nitrate
See page B 264 for the meaning of Abbreviations
 I

B 272

Explosive Brisance Brisance Power

by Kast Relative Density Method Relative Density Deton Density Method Relative
“B %TNT d of %TNT d Velocity d of % TNT
(x 106) g/cc Detg g/cc m/see g/cc Detg

Dinitroaniline(DN .4) — — — — — BhlT 88

Dinitroanisole( DNAns) — — — — — — BMT 87

Dinitrobenzene(DNB) 64 74 1.50 ST 7482 - 6100 1.56 TT 79-86

CCCT 80 1.50 BMT 90

2,6-Dinitro-2,6-bis- See 2,6-Dimethylol-2,6-dinitro-1, 7-heptanediol Tetranitrate

hydroxymethyl- l,7-hep-
tanediol Tetranitrate

2, .5-Dinitro -2,5-bi~ See 2, >Dimethylol-2, >dinitro-1 ,6-hexanediol Tetranitrate

hydroxymethyl-1,6-hex-
anediol Tetranitrate

Dinitrochlorohydrin See Glycerol Monochlorohydtin Dinitrate

Dinitrodicldorobenzene — — L BCT 69 1.69 — 13MT 86

(Parazol)
Dinitrmiimethyloxarnide — — — ST 71 7050 1.5 TT 105
(h@JO) FGT 98 1.45 Bhff 12935

Dinitrod imethylsdfamide — — — — — — — BMT 126

!linitrodi(fi-nitroxyethyl) — — FGT 116 1.62 784)0 1.63 TT 145

oxamide(NENO) BhIT 129-35

Dinitroe thane — — — — — — TT 150

BMT 127-42

Dinitroethyleneure a — — — ST 109 7650 1.6 TT 120

( DNELJ) BhfT 130

Dinitrofuran — — ST 90 — — —

Dinitrogiycerin See Glyceroldinitrate

Dinitrophenol(DNPh) — — — ST 52 — — — BMT 52

3,5-Dinitrophenyl- — — — — — TT ca100
nitrome thane

2-(3’, 5’-DinitrophenyI) — — — — BMT 126

- 2-nitro- 1, 3-propane-
diol Dinitrate

1,4-13initropiperazine — — — — — TT 114
Bhff 107
See page @ 266 for the meaning of Abbreviations

1
 B 273

ExpIosive Brisance Brisance Power

by Kast Relative Density Method Relative Density Deton Density Method Relative
!ZTNTd”of % TNT d - Velocity d - of %TNT
(x :06) g/cc &?tg g/cc dsec g/cc Detg

2, 2-Dinitropropane — TT 130
BMT 123

2, 2-Dinitro-l-propanol — — — BMT 122

2,4Dinitrotoluene(IlNT) — LBCT 77 1.3 TT 64

r3MT 71

Di(/?Lnitroxyethyl) — — Bhm 142

-nitramine

Dinitroxypentamethylene — — 7895 1.35 EMT 155

tetranitramine(’ ‘106”)

Dipentaetythritol 148 172 1.63 ST 119 – 7450 1.63 TT 128

Hexanitrate(DPIWN) BMT 144

Dipicrylamine See Hexanitrodiphenylamine

.
Dipicrylethylenedi- — — — B MT 123
nitramine

Dipicryl Sulfide See HexanitrodiphenyI Sulfide

~itettyl (Brit) See Trinitrodi(methylnitramino)-benzene

Ditetryl (US) or See N,N’ -(Hexanitrodiphenyl )-e&ylenedinimmke

Octyl(Brit)

Dithekite(Nitric Acid — TT 110-24

/’Nitrobenzene/H20) BAm 124

Di(2,2,2-trinitroeth yl) — — TT 147-8

-nitratnine or B is(2,2,2 Bhff 134-55
-trinitroethyl)-nirram ine
(BTNENA or HOX)

Di(2, 2, 2-trinitroethyI) — TT 169

-urea or Bis(2, 2,2-tti- BMT 144
nitroethyI)wres(BTNEU)

Donarite(AN 80,gelatin- 51 59 1.3 CCCT 56 1.3 4000 1.14

ized NG 4 ,TNT 12 &
linseed flour 4%)

Dtdcitol Hexanitrare — Bkfr 145

Dunnite or Explosive D See Ammonium Picrate

See page B 266 for the meaning of Abbreviations
 1

B 274

Explosive Brisance Brisance Power

by Kast Relative Density Method Relative Density Deton Density Method Relative
of %TNT d Velocity d of %TNT
(x1 06) b %tnbt Detg g/cc m/see g/cc Detg

Dynamite, Guhr, 75%(NG CCCT 68%NG 1.50 6800 1.50 TT 105

75%& kiese Iguhr 25%) TT 59%NG

Dynamite, Straight, 60% — — 5900 BPT 114

(NG 56.8,Na nitrate 22.6,
woodmeal 18.2, antacid 1.2
& moisture 1.2%)

Dynamite,Srraight, 50% — — — 5200 — BMT 102.5

(NG 49.O,Na nitrate 34.4,
woodmeal 34.4, antacid
1.1 & nmis tute 0.%0)

Dynsmite,Straight,40% — — 4400 BPT 94.5

(NG39.O,Na nitrate 45.5,
woodmeal 13.8, antacid 0.8
& moisture 0.90) (See also Blasting Gelatin and Gelatin Dynamites)

Ecrasite See Ekrasit

EDDN See Ethylenedimine Dinitrate

EDNA or Haleite See Ethylenedinitramine

Ednafive(EDNA50 & — PDT 111 cast — Bhff 130

Fivonite 5WO)

E dnatol,60/40(EDNA — — ST 112-7 7475 1.60 TT 117

60& TNT 40%) F??T 113-41 1.62 Bhff 11921

Ednatol,55/45(i?DNA — — — ST 103 7340 1.63 TT 119

55& TNT 45%) FET 124 122 Bhff 120
P!?T 105 1.62

Ednatol,50/50(EDNA — FET 109 1.62 7264 1.63 BMT 112-17

50& TNT 50%) PDT 105-11 1.62

Ednatolal(EDNA40, — — — BMT 130

TNT40&Al 20%)

Ekrasit(Ecrasite ) See Note under Ammonium Trinirrocresylate@otassium Nitrate

EhMET See Ethyltrimethylolmethane Trinitrate

Erythritol Tetranitrate — ST 132-43 – - – BMT 151

(Terranitroerythrite)

EthanoInitrarnine(NENA) See N-@-Nitroxyethyl} nitramine

See page B 266 for the meaning of Abbreviations
 B 275

Explosive Brisance Brisance Power

by Kast Relative Density Method Relative Density Deton Density Method Relative
B %TNT d of %TNT d Velocity d of % TNT
(x 106) g/cc Detg g/cc dsec - g/cc Detg

Ethylenebis(ethsnol- BMT 134

nitramine)-dinitrste

Ethylenedismine ST 96 4940 0.9 T-r 121

Dinitrate(EDDN) PDT 101 1.525 BMT 112-28

EDDN/AN-50/50 PDT 51 1.60 BMT 123

EDDN/AN/TNT BMT 124

- 20/60/20

EllDN/AN/RDX BMT 132

-35/35/30

EDDN/TNT-45/55 BMT 109

Ethylenediamine BMT 135

Diperchlorate

Ethylenediammoniunr TT 173
dinitroform BMT 149

Ethylenedinitramine ST 119 7883 1.55 TT 124-43

(EDNA or Haleite) PDT 113-22 1.5-1.6 BMT 136-40
FET 13647 1.50

EDNA/Ctowm FET 133 1.50

Oil-98/2

Ethyleneglycol Dinitrate See Nitroglycol(NGc)

Ethyl Nitrate BMT 123

Ethyl Tetryl See T rinitrophenylethylnitramine

Ethyltrimethylol- ST lC$-15 BMT 127

methane Trinitrate TT 13246

Explosive D See Ammonium Picrate

Fivolite(Tetramethyl- 7360 1.57

olc yclopentanol Penta-
nitrate or Nitropentanol)

Fivonite@V) (Tetra- PDT 106-12 1.54 7300 1.57 TT 129

tnethylolc yclopentanone BMT 121-2
Tetranka te OKNitro-
See page B 266 for the meaning of Abbreviations
pentsnone)
 B 276

Explosive Brisance Brisance Power

by Kast Relative Density Method Relative Density Deton Density Method Relative
%TNT d of %TNT d Velocity d of %TNT
(x ?&) g/cc Detg g/cc m/see g/cc Detg

Fv/EDNA-50/50 See Ednsfive

Fv/PETN-50/50 See Pentsfive

FV/RDX-47/53 See Cyclofive

Galactsn Trinitrate — ST 88 - —

Gsmsit(AN 60,NG 21, Expl characteristics are similar to those of Telsit

NGc 5 ,NC 1.6,1iq DNT
12& Woodmeal 0.4%)

Gelatin D ynamite,65% 112 130 1.66 CCCT 130 1.66 7000 1.66 TT 13>56
(NG62.5,NC 2.5,wood-
meal 8.0 & KC104 27.WO)

Gelatin Dynarnite,60% 96 112 1.6 — . — 6200 1.6 BPT 99

(NG49.6,NC 1.2,Nanittate
38.9, woodmeal 8.3,sntacid
1.1 &nmisture 0.9%)

Gelatin Dynamite 50% - PDT 69 1.24 5600 1.5 BPT 90.5

(NG40. l,NCO.8,Nanitrate
45.6,S L3,antacid 1.2&
moisture 1.2%)

Gelatin Dynamite 4074NG - — 5200 BPT 84.5

32.0,NC 0.7,Na nitrate
51.7,S 2.2,antacid 1.2 &
moisture 0.9%)

Gelatin Penttinit(NG65, - — 8000 1.65 TT 164

PETN16.5,NC4,AN 13.5
& DNT or TNT 1%)

Glycerol Dinitrate or - — LBCT 135 1.51 — TT 153

Dinitroglycerin

Glcerol Monochlorohydtin - — LBCT 83 1.54 — TT 135-53

IXnittate or a-Dinitro-
chlorohydtin

Glycerol Monolactate – — BMT 114

Trinitrate

Glycerol Trinitrste See Nitroglycerin@G)

See page B 266 for the meaning of Abbreviations

 B 277

Explosive Brisance Brisance Power

by Kast Relative Density Method Relative Density Deton Density Method Relative
%TNT d of %TNT d Velocity d of %TNT
(x :06) g/cc Detg g/cc m/see g/cc Detg
— Brisamce is comparable - — TT 137-40
Glycerol- a (2,4,6-tri-
nitrophenyI ) Ether Di- to Tetryl BMT 114
nitrate or Trinitril

Glycol Dinitrate See Nitroglycol(NGc)

Guanidine P ercfdorate 7150 1.67 TT 130

BMT 124

Guanylnitrosaminoguanyl- See Tetracene

terrazene

Guanylurea P erchlorate — BMT 92

Guhr Dy namite (NG 75.8 88 1.50 CCCT 86 1.50 670U 1.62 TT cal10
75& kieselguhr 25%)

Guncotton See Nitrocellulose(N 13.2-13.4%)

H-6( one of the HEX See Ref 30a,p 388(Conf)

expls)

Haleite See Ethylenedinitramine(EDNA)

HEX’s(High Blast Ex- ifiodifications of Torpex. Expl characteristics are given in Ref 30a,pp 382-7(COnf)
plosives) (US Navy )

HEX-1(RIX39.6,TNT — PDT 1~ 1.73 7400 1.69 BhfT 133

37.8,.41 17.l,desensitizer (See also Ref 24b,p 45 & Ref 28,pp 198-9)
D2 5.O&Ca chloride 0.5%)

Heptryl or 2,4,6-Tri- — BAm 143

nitrophen yl-rrimethylol- Note: Described as N(2,4,6-trinitro-N-aniline)-trimethylol Trinitrate in
methylnitramine Trinitrate Vol l,p A442-L

HEX(High Energy See Ref i30a,pp 394-401(Conf)

Explosive)

Hexamethylene-triper- ST 99 – 5100 1.1 TT 60

oxide-diamine(HMTPDA
or HMTD)

Hexamethylolbenzene Bhm 138

Hexanitrste

Hexamine D ipe~chlorate 7 — TT ca130

Hexarnite(TNT 60, — — ST 116 - 690 1.72 TT 116

HNDPhA 24&Al I’6%) Cornpate with Novit BMT 130
See page 6266 for the meaning of Abbreviations
.
.. ..
 I

0278

Explosive Brisance Brisance Power

by Kast Relative Density Method Relative Density Deton Density Method Relative
B %TNT d of %TNT d Velocity d of % TNT
(x 106) g/cc Detg g/cc m/see g/cc Detg
Hexanit(Ger) See Hexanitrodiphenyl amine

Hexanitroazobenzene — — — TT 122
(See also Vol l,p A649-R)

Hexanitrobiphenyl Some expl characteristics are given in this volume under Biphenyl and
Derivatives

Hexanitrodiphenyl amine 111 129 1.67 ST 117-20 – 7400 1.64 TT 102-8

(HNDPhA or HNDP) CCCT 114 1.64 – – BMT 111-15

@-(He xanitrodiphenyl- — — ST 120 1.27 – - TT 1%

Srnino}ethanol Nirra te

N,N’ -( Hexanitrodiphenyl) — — — — — TT 123

-ethylenedinitrarnine BMT 123
[Ditetryl (US),Octyl(Brit)] Some expl characteristics are given in this vol under Bis(anilino)-eth ane

Hyman See Nitromethylglycol amide Nitrate

Inositol Hexanitrate ST 134 — — — — —

IGesilit (Austrian) See Trinitrocresol

Lactose Ocranitrate — — — ST 134 — 4225 1.6 —

Lead Azid4LA)(pure) 74.9 87 3.8 ST 37-40 5300 4.6 TT 41-4

FET 17.4 4.83

Lead Azide, dextrinated — ST 35-8 — 5CQ0 4.0 TT 38-43

Lead Dinitroresorcinate — ST 42 — — —
(LDNR)

LDNR, Basic — — ST 31 — — —

Lead Styphnare(LSt) or 63.7 74 2.6 ST 27-53 5200 2.9 TT ’42

Lead Trinitroresorcinate 75 87 3.1
(LTNR)

Liquid Oxygen Explosive 45 52 0.8 — — 4700 0.8 —

(Carbon 27.3 &liqO 72.7%)

Liquid Oxygen Explosive 113 132 1.(X — 5600 1.(35

(Cuprene 24.8 &liq0 75.2%)

See page 6266 for the meaning of Abbreviations

 B 279

Explosive Brisance Brissnce Power

by Kast Relative Density Method Relative Density Deton Density Method Relative
%TNT d of %TNT d Velocity d ?%TNT
(x !06) g/cc Detg g/cc m/see g/cc D~g

Low Veloci~ Dynamite — ST 84 - 4400 0.9 – –

(LvD) [TNT67.8,tripenta- Note: RDX, Class E consists of R13X99.5 & l-MA dye 0.5%, 1-MA dye is $X5%pure
erythritol 8.6, cellulose l-methylamino-anthraquinone; Vistac/~ binder consists of Vistac NO 1
acetate(LH-1) 2. O,RDX (low mw polybutene)68 & DOS (dioctylsebacate) 32%
(Class E) 17.5 Vistac
/DOS binder 4.1%]

Lyddite(Brit) See Picric Acid

Makarit or Macstite ST 68 4850 2.89

(TNT30&Pb nitrate Cccr 90 2.75
70%), also called
Plumbatol

Maltose Octsnitrate ST 113 L62

HexanitrodiphenyI- — — TT 110
sulfide (DipictyI-
sulfide)

Hexanitrodiphenyl- — TT 115
stdfone

Hexanitrodiphenylure a ST 84 BMT 76

Hexsnitroethsne -. BMT 108

Hexanitroinositol See Inositol Hexanitrate

Hexanitromsnnitol See hiannitol Hexsnitrate

Hexanitro6xanilide ST 134 TT 76

Hexsnitrosobenzene — — TT 156
BMT 147

Hexil of Hexite See Hexanitrodiphenylamine

Hexogene See Cyclotrimethylenetrinitramine

Hexonit, 80/20 (RDX Expl characteristics are similar to those of Pentrinit, 80/20
80& NG 20%)
Hexotol(Swed) Expl characteristics are similar to those of Cyclotols
(RDX/TNT)

Hexotonal(Swed) Expl characteristics are similar to those of Torpex

(RDY/TNT/Al)

HNDT See Hexamethylenetriperoxidediamine

See page B 266 for the meaning of Abbreviations
 I

B 280

Explosive Brisance Brisance Power

by Kast Relative Density Method Relative Density Deton Density Method Relative
B %TNT d of %TNT d Velocity d of % TNT
(x 106) g/cc Detg g/cc m/see g/cc Detg

HMX(His Majesty’s See Cyclotetramethylenetetrtiitramine

Explosive or High
Melting Explosive)

HNDP See Hexanitrodiphenylamine

Holtex Swiss military expl of unknown compn, claimed to be very bris ant and powerful

HOX (High Oxygen Designation for Di(2,2,2-trinitroethyl)-nitramine, also called Bis(2,2,2-trinitro-

Explosive) ethyl)-nitramine (BTNEN)

HTA (High Temperature, See Ref 30a,pp 402-5 (Conf)

Aluminized)

Hydrazine Nitrate — — — — TT 13@2

BMT 130

Hydrazine perchlorate — — — — — — — TT 120

Manni tol Hexsnitrate 174 201 1.7 ST 137-43 8260 1.7 TT 172-96
or Hexanitromannitol PCT 122-32 1.7 BMT 136-50

MeDINA See Methylenedinitrarnine

Medium Velocity — — ST 110 1.1 – – – –

Dynamite (MVD) (RDX Note: ,Vistanex oil gel consists of SAE No 10 oil 80, Vistanex B-120XC 15&
75, TNT 15,stsrch 5, Navy I?2 wax 5%
SAE No 10 oil 4&
Vistsnex oil gel l%)

MeEDNA See N-MethylethyIenedinitramine

Melinite(Fr & Rus) See Picric Acid

MeNENA See l-Nitroxytrimethylene-3-nitrsmine

Mercuric Fulminate 83.5 97 3.3 ST 49-55 – 5400 4.42 TT 51-54

MF/KC103-90/10 74.1 86 3.1 – — — —

Methyl amine perchlorate 143.1 167 1.3 – — TT 163

Methylarnmonium Nitro- — — — — — n 185

form

Methylenedinitrarnine — — — ST 127-31 – 8500 1.68 TT 188-210

(MeDINA) 13MT 1548

See page B 266 for the meaning of Abbreviations

1
 Explosive Brisance Brisance Power
by Kast Relative Density Method Relative Density Deton Density Method Relative
of %TNT d Velocity d of % TNT
(x ;0c Detg g/cc m/see g/cc Detg

N-MethylethyIenedinitra- BMT 121

mine (MeEDNA)

a -Merhylgl ycetol Tri- ST 113 7270 1.60 BMT 140

nitrate or 1,2,3-Butane-
triol Trinitrate

~ -MethyIglycerol Tri- ST 112

nitrate or 2-Methyl-1,2,3
-propanetrioI Trinitrate

@-(N-Methyltitramino) BMT 137

-ethyl Nitrate

Methyl Nitrate PCT 240 1.20 8000 1.20 TT 183-96

LBCT 185 1.20 BPD 225

MethylnittopropanedioI See Nitroisobutylglycol Dinitrate

Dinitrate

Methyl Tetryl See Trinitromethylnitraminotoluene

Methyltrimethy Iolmethane See Metriol Trinitrare

Trinitrate
Metriol Trinitrate@fTN) 1.47 - 150
or Pentaglyce rin Tri- [See also P~TR 251~1958)~Ger 13 134-6
nitrate

Minex(TNT40,RDX 5-15, This is one of the DBX’S (See also Ref 28,p 198)
AN 25-35 &Al 20%)

Minol 2 (AN40,TNT40 ST 95 - 6000 1.70 TT 163

& Al 20%) PDT 62-66 1.641.73 BMT 143

MNo See Dinitrodimethyloxamide

Monochlorohydtin See Glycerol Monochlorohydrin Dinitrate

Dinitrate

MOX(Metal Oxidizer See Ref 30Ap 406(Conf)

Explosives)

MvD See Medium Velocity Dynamite

NENA or l-Nitrarnino See N-@Nitroxyethyl)-nitramine or Ethanolnitramine

-2-ethanol Nitrate

NENo See Dinitrodi I@ -nitroxyethyl)-oxamide

See page B 266 for the meaning of Abbreviations
 I

B 282

ExpIosive Brisance Brisance Power

by Kast Relative Density Method Relative Density Deton Density Method Relative
%TNT d of %TNT d Velocity d of %TNT
(x ‘?06) g/cc Detg g/cc rn/sec g/cc Detg

Nitrocellulose(Nca 14%) — ST 109-20 1.3 —

Nitrocellulose(N 13.2 77 90 ST 105 7300 1.3 TT 13($.47

-13.4% (Guncotton) CCCT 84 1.3 BMT 118

Nitrocellulose(N 12.6 ST 94-98 1.3

-12.7%) (Pyrocotton)

2-Nitro-2-(3’, 5’ -dinitr~ — — BiW 126

phenyI}propsnediol
-l,+dinitrste

Nitroform See Trinitromethane

Nitrogen Dioxide/Nitro- 139 162 1.38 8500 1.38

benzene-70/30

Nitroglycerin 145.9 170 1.6 ST 120 1.6 7700 1.6 TT 185

LBCT 115 1.6 BMT 140

Nitroglyc o1(NGc) or 158 184 1.50 ST 129 8000 1.49 TT 20045

Ikhyleneglycoldi- LBCT 115 1.49
nitrste(EGDN)

Nitrogusnidine(NGu) ST 814 8100 1.70 TT 78-101

or Picrite LBCT 73 1.5 Bl@ 104
PDT 95 1.5

Nitrohexano 1 See Sixolite

Nitrohe xanone See Sixonite

Nitrohydrene(NG 80 & — TT 175

Nitrosugar 20%)

Nitroisobu@glycerol 168 195 1.68 7860 1.64 TT - 200

Trinitrsre (NIBGTN)

Nitroisobutylglyc 01 — ST 113 TT 165

Dinitrste(NIBGcDN) BMT 134-8

Nitrolit(AN 40 & Expl characteristics similar to those of Amstol, 40/6qRef 24,p 110-11)
TIwls 60%)

Nitromannite See Mannitol Hexsnitrate

Nitromethane — — — 6210 1.13 TT 13843

See page B 266 for the meaning of Abbreviations BMT 1334

I
 B 283

Explosive Brisance Brisance Power

by Kast Relative Density Method Relative Density Deton Density . Method Relative
B %TNT d of %’INT d“ Velocity d of %TNT
(x lob) g/cc Detg g/cc rdsec g/cc Detg
Nitrometh ylglyco I amine – - - - 7420 1.5 BMT 133
Nitrate (Hyman)

N-Nitro-N-methyl- — 7420 1.50 BMT 132

hydroxyacetamide
Nitrate

2-Nitro-2-(m-nitrophenyl) - - - - Bkfl’ 114

-propanediol- 1, 2-dinitrate

Nitro penta or Nitre- See Pentserythritol Tetranitrate

pentaerythrite

rn-Nitrophenyl- BMT 100

dinitromethane

Nitrophenylnitromethyl- - – - - BMT 99
carbinol Nitrate

Nitropicramide See Trinitrophenylnitramine

Nitrosorbitan Tetra- — BMT 133

nitrate

Nitrostarch(NS) CCCT 83 0.9 6190 0.9 TT 145

(13.35-13.45% N) BMT 120

Nitrostarch(NS)( 12.87XQ) - - - CCCT 75 0.9 5300 0.9 TT 127

J3MT 114

Nitrostarch(NS)( 12.12%N) - - - CCCT 46 0.9 4480 0.9 TT 108

Nitroatarch Demolition - - - ST 82 —
ExpIosive(NSX)~S( 12.5% (See also Trojan Explosive)
N)49,Ba nitrate 40, MNN7, (Compare with lknolition IGrplosive, described in Ref 28,p 207)
p-MNA 3 & oil l%]

Nitrosucrose See Sucrose Octanitrate

Nitrote@ See Tetranitro phenylmethylnitramine

Nitrourea ST 60--- BMT 105

N-(@-Nitro~ethyl ) — — BMT 134-48

-nitramine(NENA~ l-Nitra-
mino-2-ethanol Nitrate or
Ethanolnitramine Nitrate

See page 8266 for the meaning of Abbreviations

 B 284

Explosive Brisance Brisance Power

by Kast Relative Density Method Relative Density Deton Density Method Relative
%.TNT d of %TNT d Velocity d of %TNT
(x :06) g/cc Detg g/cc rrJsec glee Detg

l-Nitroxytrim ethylene-3 — — — BMT’ 136

-nitramine (Me NENA)

Novit,60/4qTNT 60 & — — ST 105 – 7000 1.5 TT 105

HNDPhA 40%) (S wedish) (Compare with Hexamit, described in PATR 251qU58),pGer88) BMT 106-9

NP (Ger) Same as PETN

Nyperit (Ger) Same as PETN

0ctol,77/23(HMX77 Expl characteristics of octol 77/23 are given in R.ef 31,pp 81415 and for Octols
& TNT23) 70/30 & 75/25 in Ref 30a,pp 424-33(Conf)

Octyl(Brit) or see N-N’ -(Hexanitrodiphenyl)-ethylenedinitramine

Ditetryl (US)

Oxytetryl See Trinitro~thyInitraminophenol

PA See Picric Acid

Paraml see Dinitrodichlorobenzene

PB-RDX(Plastic See Ref30a,p434(Conf)

Bonded RDX)

PE-l(Brit plastic expl) See Ref 24b,pp 299. It was replaced by PE-2
(RDX88.3&special PE
oil 11.7%)

PE-2 (Brit) Same as Composition C(See also Ref 24b,p 29)

Pentaerythritol 172.8 200 1.69 ST 129-41 - 8300 1.70 TT 161-81

Tetranitrate(PETN) 183.7 214 1.69 LBCT 130-7 1.41.5 Bhff 137-45
or Penthrite 193 225 1.7 PDT 127 1.5-1.6

PETN/Aristowsw95/5 FET 147 1.65

PETN/Pentowax-87/13 FET 139 1.61

PETN/Aristowax-80/20 — FET 124 1.54

P entaerthritol Tri- Some expl characteristics are given in Ref 30a,pp 440-9(Conf)
nitrate (PETRIN) and
PETRIN Acrylate

Pentamethylenetetr amine TT ca 180

Dinitrare
Pentsnitroaniline (PNA) — — — — TT 15979
See page B 266 for the meaning of Abbreviations BMT 142
 B 285

Explosive Brisance Brisance Power

by Kast Relative Density Method Relative Density Deton Density Method Relative
or 74 l“N1” Velocity d of %TNT
Detg gjcc rn/sec g/cc Detg

Pentsnitrophenylmerhyl- — TT 152
nitramine

Pentastit,93/7(PETN CCCT 122 1.56 8000 1.56 TT 140

93 &PE-tetrastesrate 7%)
(Swiss)

Pentastit,93/7 with 20% CCCT 116 1.68 7700 1.68 TT 161

Al

Pentastit,96.5/3.5(PkTN ccc-r 127 1.60 8100 1.60 TT 144

95. 5& PE-tetrastesrate
3.5%)

Pentastit,x.5 /3.5 with — CCCT 117 1.67 7700 1.67 TT 176

20% Al

Pentol(Ger) See Pentolite

Pentolite, 75/25(PETN Note: Stettbacher used the term “Pentryl” to designate mixts PETN + TNT
75& TNT 25%)

Pentolite,70/30 ST 131 7800 1.58 TT 136

(PETN70 &m 3 o%) CCCT 121 1.58

Pentolite, 70/30 with CCCT 122 L65 7400 1.65 TT 171

15% Al

Pentolite,60/40(PETN ST 127 7620 1.66 TT 127

60& TNT40%) PDT 113 1.6 BMT 127
CCCT 118 1.56

Pentolite,60/40 with — CCCT 117 1.68 7200 1.68 TT .168

15% Al

Pentolite,50/50(P~N ST 123 7510 1.66 TT 121

50& TNT 50%) PDT 111 1.6 Bhff 122
FET 131 1.65
CCCT 113 1.55
Pentolite,50/50 with CCCT 117 1.62 7000 1.62 TT 155
15% Al BMT 126

Penrolite,40/60(PETN ST 118 7370 1.65 BMT 118

40& TNT 6%)

Pentolite,30/7~PETN ST 113 —
30& TNT 70%)

See page $266 for the meaning of Abbreviations

 4

B 286

Explosive Brisance Brisance Power

by Kast Relative Density Method Relative Density Deton Density Method Relative
%TNT d of %TNT d Velocity d of % TNT
(x :06) g/cc Detg g/cc nt/sec g/cc Detg

Pentolite ,25/75(PETN — ST 111 - 7150 1.62 Bhm 111

25& TNT 75%)

PentoIite, 10/90(PETN ST 105 - - – - -

10& TNT 90%)

Pentonal,47/33/20 Expl characteristics not found it was, however, stated that it is very sensitive
(PETN47,TNT 33&AI to btdlet impact(Ref 24b,p 33)
20%)

Pentrinit,80/20(P ETN 178 208 1.72 – – - 84C0 1.72 TT 179

80&NG 20%)(Swiss)

Pentrinit,50 /50 (PETN 8000 1.65 - —

50& NG 50%)

Pentrinit,50/50 with — 7200 1.9 -

30% Al

Pentritol(Ge r) See Pentolite

Pentry 1 Stettbacher’s name for mixts of P ETN and TNT, called Pentolite in the US

Pentty 1 or Trinitro- ST 129 – 7340 1.65 TT 130

nitranilinoethanol LBCT 125 1.6 BMT 12433
Nitrate PCT 117 -
FET }110

PEP-2(PETN85 &Gulf BMT 115

Gown Oil E 15%) (See also Ref 24b,p 30)

PEP-3(PETN86&Gulf — ST 106 – 7778 1.47 BMT 115

Crown Oil E 14%) PDT 100 1.50
FET 124 1.51

PETN See Pentaerythritol Tetranitrate

PETRIN See Pentaerythritol Trinitrate

PETX See Tetra(nitrarninomethyl}methane

PicramirIe See Trinitroaniline

Picratol,52/48(Amm — ST 94 - 6970 1.67 BMT 100

picrate 52 & TNT48%) PDT 100 1.63
FET 102 1.61
Note: It is called Picrotol in Ref 24b,p 32

See page 6266 for the meaning of Abbreviations

 B 287

Explosive Brisance Brisance Power

by Kast Relative Density Method Relative Density Deton Density Method Relative
B %TNT d of %TNT d Velocity d % TNT
(x 106) g/cc Detg g/cc rn/sec g~cc D~g

Picric Acid(PA) or 107.4 125 1.69 ST 103-10 - 7460 1.70 TT 10317

Trinitrophenol 118.1 137 1.63 CCCT 114-23 1.6-1.69 B~ 1%12
PDT 107 1.6
FET 122 1.70

Picrite See Nitrogusnidine

Picrotol Same as Picratol

Picryl Axide BMT 139

Picryl Chloride(Tri- CCCT 114 7130 1.75 T-T 103-10

nitrochlorobenZene )

Picrylnitramine See Trinitrophenylnitramine

PIPE(PETN81&Gulf ST 87-94 7075 1.37 TT 1(X

Crown Oil E 1%.) PDT 76 1.33
FET 79 1.36

PIumbatol See Macsrite

PI-x,90/5(Nitiomethme ST 105 1.12 6165 1.12 —

95& ethylenediamine 5%)

Polyvinyl Nitrate(PVN) ST 104-7

Potassium Dinitroben_ ST 93 2,2

furoxan(KDNBF)

Propanediol Dinitrate See Trimethyleneglycol Dinitrate

Propargyl Picrate TT 95
B~ 99

Propylenedinitra- See Trimethylenedinitr&e

mine(PDNA)

Propyleneglycol — TT 155
Dmitrste

PTX-l(RDX 30,TetryI 50 ST 119-22 8000 168 BMT 132

& TNT 20%) PDT 427 1.68
FET 135-7 1.68

PTX-2(RDX43.2,PETN ST 125-7 8065 1.70 BMT 138-45

28& TNT 28.WO) PDT 141 L71
FET 153 1.68
see page B 264 for the meaning of Abbreviations
 1

-..
B 288

Explosive Brisance Brisance Power

by Kast Relative Density Method Relative Density Deton Density Method Relative
% TNT d - Velocity d ‘ of %TNT
(X !06) ‘m g$cc D;tg g/cc dsec g/cc Detg

PVA-4(Polyvinyl acetate ST 122 – 7910 1.60 —

6-S,RDX 92-90 &dibutyl-
phthalate 2)

PVN See Polyvinyl Nitrate

RDX(Resesrch Depart- See Cyclorrimethylenetrinitramine

ment Explosive)

RDx Polar PE(RDX88 Expl characteristics similar to Composition C

&95/5 mixt of Gulf 300 (See also Ref 24b,p 29)
Process Oil/Lecithin
12%)

RIPE(RDX85 &GuIf — — ST 84-91 7390 1.37 BMT 118

Crown Oil E 15%) FET 89 1.39 — —
PDT 85 1.37 — —

Shellite(Brit) See Tridite,70/3 O

Shimose(J ap) See Picric Acid

Silver Acetylide 94 109 4.0 — — — —

Silver Axide — ST 40-3 — — — —

FET 66 4.97

Sixolite(Tetramethyl- — — 7430 1.58 TT 135

okyclohe xa noI Pent a- Bbff 127
nitrate or Nitrohexanol)

Sixonite(Tetramethyl- . — — 7740 1.51 Bhff 114

okyclohexartone Tetr -
nitrate or Nitrohexanone)

Styphnic Acid See Trinitroresorcinol

Sucrose Octa nitrate — TT 102

Telsit(Swiss) (AN — LBCT 93 1.55 6000 1.55 TT 129

55.5,NG22,NC 1.5&liq (Ref 10,p 242)
DNT with TNT 21%)

Tetracene or Guanylnit- — ST 4070 — TT 51-63

rosaminoguanyl tetrazene

Tetramethylolcyclohex- See Sixolire

snol P entanitrate
See page B 266 for the meaning of Abbreviario ns
 B 289

Explosive Brisance Brisance Power

by Kast Relaitve Density Method Relative Density Deton Density Method Relative
%!I’NT’ d Velocity d of %TNT
(x ;0f5) ‘~ ~dcc :~g g/cc tn/sec g/cc Dug

Tetramethylolcyclohex- See Sixonite

anone Tetranitrat e
Tetramethylolcyclm See Fivolite
pentanol Tetranitrate
Tetramethylolcyclo- See Fivonite
pentanone Tettanitrate
Tetra(nitraminomethyl) BMT 129
-methane,designated
PETX

Tetranitroaniline(TeNA) ST 102 - 7630 1.6 TT 130-49

Note: According to some investigators TeNA is more brisant BMT 121
than Tetryl (See also Vol l,p A4H-R) BPT 146

Tetranitroanisole(TeNAns) — TT 131-8
(TeNAns) (See also VOI l,p A454R)

Tetranitro hen zene(TeNB) — — TT 150

(See also Vol 2,under Benzene)

Tetranitrobutane — — TT 176-9
(TeNBu) (See also Vol 2, under Butane) BMT 146-53

Tetranitrocarbazole ST M5-95
(TeNCbz)

Tetranitrodiglycerin ST 108 TT 150-9

(TeNDG)

Tetranitromethane ST 108 6400 1.65 TT 54

Tetranitromethane/ 7700 1.5

Nitrobenzene -77. 2/22.5

Tetranitrometharie/ 212 246 1.45 — —

Toluene-86.5/13.5

Terranitromethylaniline See Tetryl

Tetranitronaphthalene BMT 101

(TeNN)

Tetranitro6xanilide ST 34 —
(TeNOx)

TetranitrophenyI- TT 1546
methylnitramine or BMT 13441
m-NitrotetxyI
See page B 266 for the meaning of Abbreviations
 B 290

Explosive Brisance Brisance Power

by Kast Relative Density Method Relative Density Deton Density Method Relative
d of %TNT
(x ‘m ;== I&
;(36) %TNT d
gicc
Velocity
dsec g/cc Dug

Terranitrotoluene(TeNT) - - - - – - - TT 127

Terrs@-nitroxyethyl) - - - - - - >8000 1.6 TT 15G 8

-ammonium Nitrare BMT 138-41

Tetrateuyl See Tetrs(2,4,6-trinitrophenylnitraminonethyl)-methsne

Tetratol See Terrytol

Tetra(2,4,6-trititro- TT 132
phenylnkrsminomethyl)
-methane or Tetrstetryl

Terroxyl See Trinitrophenylmerhoxynitrsmine

Tetryl(US) or CE(Brit) 114.9 134 1.63 ST 113-23 - 7850 1.71 TT 125-45

(Trinitrophenylmethyl- CCCT 117-25 1.5 Y1.63 BMT 126-32
nitramine or Trinitro LBCT 112 – BPT 145
-N -methylnitramine) PDT 115 1.59
FET 121 1.60

Tetrytol,80/2 O ST 122 - 7425 1.64 BIW 123

(TeuYl@&~2WO) – - -

TerrytoI,75/25 ST 120 - 7390 1,62 BMT 122

(Tetryl 75& TNT25%) PDT 114-19 1.62-1.66
FET 120 1.60

Tetrytol,70/30 — ST 119 - 7350 1.61 BMT 120

(T@ryl70&TNT30%) PDT 117 1.60 TT 120
FET 119 1.60
Terryrol,65/35(Tetryl - - - ST 118 - 7310 1.60 BMT 119
65& TNT 35%) FET 118 1.60

Tetrytol,40/@Tetryl - - - ST 113 - 7120 1.62 BMT 112

40& TNT 60%) FET 113 1.60
Note: Terryrols are listed in Ref 18a as Tetrsrols

TNA See Trinitroaniline

TNAns See Trinitroanisole

See Trinitrobenzene

TNN See Trinitronaphrhslene

See Trinitrotoluene

Tol or Tolite See Trinirrotoluene

See page B 266 for the meaning of Abhreviarions
 B 291

Explosive Brisance Brisance Power

by Kast Relative Density Method Relative Density Deton Density Method Relative
.-. .
%TNT d of %TNT d Velocity d of % TNT
(x !06) g/cc Detg g/cc RJsec g/cc Detg

Torpex(RDX45,TNT ST 122 7495 1.8 TT 161-2

37&AI 18%) FET 126 1.75 Blvm 132-50
PDT 120

Torpex-2(RDX 42,TNT ST 132-60 7660 1.80 TT 140-66

40& Al 18%) PDT 11619 1.80 (Refs 24& 24b) BMT 134?64
FET 126 1.77
Triaminotrinitrobenxene See Ref 30a,p 454(Conf)

Triazidotrinitrokenzmne PPT 1.58 1.75 TT 165-71

(TATNB) BMI’ 147

Tricycloacetone ST 80 5300 1.18

Peroxide

Tridite,70/3MUS\ — ST 89 6600 1.6 TT 95

Shellite(Brit) (PA 70 BMT 91
& HNDPhA 30%)

Tridite,60/40(PA 60 ST 84 63OO 1.6 TT 92

& HNDPhA 4 o%) BMT 90

Tridite,90/10(PA 90 ST 100 7000 1.6 TT 102

& HNDPhA lWO ) (Ref 24,P 57, table) BMT 100

Triethyleneglycol ST 31 1.32
Dinirrste(TEGDN)

TrirnethyIenedinitramine BMT 116

or Propylenedinitramine
(PDNA)

Trimethyleneglycol- 1.39 TT 80-90NG

Dinitrst4TMGcDN) or
Propsnediol Dinitrste

Trimethylolethane See Metriol Trinitrste

Trinitrste or Nitro-
pentaglycerin

Trimethylolnitro- See Nitroisobutylglycerin Trinitrste

methsne Trinitrate

Trimethylolpropane ST 108-15 - TT 132-46

Trinitrste or Ethyl- BMT 127
trimethylolmethsne
Trinitrate(EMMET)

See page B 266 for the meaning of Abbreviations

 B 292

Explosive Brisance Brisance Power

by Kast Relative Density Method Relative Density Deton Density Method Relative
% TNT d - Velocity d of % TNT
(X ?06) %- g$cc Dt~g g/cc m/see g/cc Detg

Trilite See Trinitrotoluene

Trimonite,90/10 — — — ST 92-7 – 7080 1.60 TT 94

(PA90&MNT 10%) BMT 95

1, 1,1-Trinitraminomethyl- — — — EM-r 112

methane

Trinitroaniline — — 7600 1.7 TT 107

(TNA) or Picramide (See also Vol l,p A41O)

Trinitroanisole 87.1 101 1.59 ST 100-1o - 7000 1.59 TT 1048

(TIW4rls) CCCT 92-100 1.59 - BW 1068
(See also Vol l,p A451-L)

Trinitrobemzaldehyde ST 117 – - TT ca la
(TNBA) (See also Vol 2, under Benzaldehyde)

Trinitrobenzene (TNB) 105 122 1.63

ST 110 – 7350 1.66 TT 105-20
110.3 129 1.63
CCCT 114 1.63 Bkm 105-17
LBCT 111 1.6
FET 117 1.7
(See also Vol 2,under Benzene)

Trinitrobenzoic Acid — ST 100 – - BMT 98

(See also Vol 2,under Benzoic Acid)

Trinitrobenzyl Nitrate — — — BMT 126-7

(See also Vol 2,under Benzyl Alcohol and Derivatives)

Trinitro-bis(methyl- See Trinitrodi(methylnitramino)-benzene (Ditetryl)

nitramino-benzene)

Trinitrochlorobenzene 106.5 124 L 74 CCCT 97 1.62 — —

(’INCIB)

Trinitrocresol( TNCrs ) 84.3 98 1.62 CCCT 97-105 1.62 6850 1.62 TT 86-99
or Cresylite BLm 94

Trinitro-di(methyl- — — TT 130
nitramino)-benzene; BiWr 123
Ditetryl(Brit)

Trinitroethanol — — TT 161-2

Trinitroethyknino- — TT 161
tetraimle

See page B 266 for the meaning of Abbreviations

 B 293

Explosive Brisance Brisance Power

by Kast Relative Density Method Relative Density Deton Density Method Relative
%TNT d of %TNT
. .. . . ,
c1 Velocw d of % TNT
(x :0% g/cc Detg g/cc m/see g/cc Detg

Trinitroethylbenzene ST 88 —
(TNEB)

Trinitroethyltrinitrc- See Ref 30a,p 459(Conf)

butyrate

Trinitromelamine — — — BMT 101

Trinitromesitylene — B MT 84

Trinitromethane — — — — TT ca100
or Nitroform BAIT 125

2,2,3-Trinirrw3 — T BMT 104 l

-methylbut ane

— — TT 112
Trinitromethyl-
nitraminotol uene BMT 110
or hkhyltetryl

Trinitronaphth alene — — BMT 83

(m

Trinitrophenetole — — 6880 cast TT 84

BMT 80

Trinitrophenol See Picric Acid

Trinitrophenoxy- Pa 90 TT 122
ethyl Nitrate

l-(2,4,6-Trinitro- BAIT 120

phenoxy>propane
-2,3-diol

Trinitrophenyl Azide PCT 117-32 TT 135-9

or Picryl Azide

Trinitrophenylbutyl- ST 100 — — .BMT 97-8

nitramine or 13utyl-
tetryl

Trinitrophenylethyl- 6200 1.6 114

nitrarnine or EthyI- 111
tetryl

I’rinitrophenylmethoxy- TT 142
itramine
See page B 266 for the meanir.g of Abbreviations
 1

B 294

Explosive Brisance Brisance Power

by Kast Relative Density Method Relative Density Deton Density Method Relative
of %TNT d Velocity d of % TNT
(, :06) ‘- ~;=c Detg g/cc m/see g/cc Detg

Trinitrophenylmethyl- See Tetryl

nitrsmine

2,4,6-Trinitrophenyl- — — — — . Bhff 117

-(1-methylol)-propyl-
nitramine Nitrate

Trinitrophenylnitrsmine;” — — — — — — TT ca 150
Nitropicrylamide or
Picrylnitramine

Trinitro phenylnitramino- See Pentryl

ethyl Nitrate
.
Trinitrophenyltri- See Heptryl
methylolmethyl-
nirramine Trinitrste

Trinitroresorcinol — ST 94 - – – TT 105-15
(TNR) or Styphnic Bhff 108
Acid

Trinirrosotrimethylene — — — BMT 134

triamine

Trinitrotoluene(TNT); 86.1 100 1.59 ST 100 – 6970 1.59 ‘IT 100

Tolite; Tel; Trotyl; ST ca80% of - (cast) TT 9G95%PA
Triton; Tritolo PETN or
RIX
(.Sand crushed by 0.4g TNT= 43-48g) (Lead block
CCCT 100 1.59 expsns caused
(Compression of Cu cylinder ca 3.5MM) by 10g TNT
LBCT 100 1.39 285-305 cc)
(Compression of Pb cylinder ca 16mm) BMT 100
PDT 100 1.59 BMT 89%PA
(Depth of dent in the plate ca 0.205mm) BMT 65.5% of
FET 100 1.59 Blasting
(Number of fragments in 90mm shell ca 703 andin3“shellca514) ‘ Gelatin

TNT+ 0.05-0. 10% span 85 — FET 97 1.59 – - - –

TNT/D2-95/5 F~T 93 1.75 — - – -

Trinitrotriazidobenzene See Triazidotrinitrobenzene

Trinitroxylene(TNX) — — — ST 84-6650 1.51 TT 93

Tripentaerythritol See Ref 30~p 465(Conf)

Octanitrate
See page B 266 for the meaning of Abbreviations
 B 295

Ezplosive Brisance Brisance Power

by Kast Relative Density Method Relative Density Deton Density Method Relative
B %TMd”of %TNT d Velocity d of %TNr
(x 106) g/cc Detg g/cc dsec g/cc Detg

Tris(methylnitramino- B~ 1(M
methyl)- smine

TritoIo (Ital) See Trinitrotoluene

Triton See Trinitrotoluene

Tritonal, 90/10 ST 111-14 - 6580 1.65 BMT 123

(TNT90&Al 10%)

Tritonsl,80/20(TNT ST lo&14 - 6770 1.76 TT 153

80& Al 20%) PDT 934 1.72-1.75 BMT 124
FET 91 1.72

Tritonal/D2-95/5 PDT 85 1.67 6560 1.68 BMT 123

Trojan Explosive ST 88 - 6100 1.6 TT 96

(Nitrostarch4 O,Na nitrate (Compare with Nitrostarch Demolition Explosive) BMT 96
37.7,Ba nitrate 20.0, oil
0.8 & DPhA or CaC03
1.5%)

Trotyl See TrinitrotoIuene

Type 98 Expl,60/40 ST 98 - 7000 1.5 TT 108

(Japsn)(TNAns 60& BMT 109
HNDPhA W.) Note: There was also 70/30 Type 98 Explosive)

Underwater Explosive Brit for Tritonal

(WE)

Urea Nitrate — — TT 91
BMT 92

Abbr for Underwater Explosive

Veltex See Ref 30a,p 470(Conf)

Xylan Dinittate — BMT 107

Xylitol Tetranitrate BMT 149

The above table was compiled in collaboration with Mr. ~rm.H.Rinkenbach, Allentown, Pemsylvania(1961)
See page B 266 for the meaning of Abbreviations

Re/s: l)H.Kast,SS 8,65-8 & 88=9(1913) (Cdcn criticized and its modification is proposed.
of brisance by Kast’s formula and brisance Herlin’s formula is more complicated than
values for some expls detd by Cu Cylinder Kast’s) lb)H. Kast,S8 9,33-4(1914) (Kast’s
Compression Test) la)C.Herlin,SS 8,448-52 reply to Herlin. He does not agree with
(1913) (Kast’s formula for caicn of brisance is Herlin’s criticism) 2)Marshall 2(1917),476
 B 296

-501 3)H.Kast, ”Spreng- und Ziindstoffe”, denting test values for Fivonite in comparison
Vieweg,Braunschweig( 1920),70 4)H.Kast,SS with some other expls) 24)AH&EnExpls( 1946),
15,171-3 & 18 I-4(1920) (Brisance valuesrfor 17-18 & table betwn pp 57 & 58 24a)D.
several expls; table) 4a) W.C. Cope,IEC 12, P. ,MacDougall et al, OSRD 5746(1946)
870(1920 )( Brisance and some other expl (Expl characteristics of many expls) 24b)Anon,
characteristics for various military expls) “Summary Report of Division 8,NDRC”,V01 1,
5)H.Kast,ZAngewChem 36,75(1923) (Brisance Washington, DC(1946) 25) S. Fleischnick,PATR
values for some expls; table) 5 a)H. Kast & 1595( 1946) (Fragment ation efficiency values for
A. Haid,ZAngewchem 38,50-2( 1925) (Brisance some expls) 25 a)?duraour( 1947),7 7-9 26)Stett-
values and other expl character sties for ini- bacher( 1948),102-4, 114 & 149 26a) W.C. Lothrop
tiating expls and some otkr expls) 6) Nao6tn, & C. R. Handrick,ChemRevs 44,419-45(1949)
NG(1928), 156,170, 190,201,204-6,224-7,235-9, (Relationship between performance and consti-
24 ,247,249-50,277-9,319,322-3 & 349 6a)Su- tution of pure organic compds) 26b)A.D. Little,
kharevskii & Pershakov( 1932), 102,120 & 150 Inc, “Report on the Study of Pure Organic Com-
7)Vennin,Burlot & L6corch6( 1932), 189-93 pounds’’,Part 2( 1949), Section 8( Relationship
8)Marshall 3( 1932), 155-7 9)W. Friederich & between heat of expIosion and power & bri-
W. Briin,SS 27,158(1932) (Brisance by Kast’s sance values) (Conf) (not used as a source of
formula) 10)Stettbacher( 1933),48-52,62-4,95, info) 27)Belgrano( 1952),5 & 39-41 27a)Stett-
363 & 368 10a)W.Friederich,SS 28,82-3(1933) bacher(1952), 131-3,144,152-3 & 189 28) Anon,
(CaIcn of “specific brisance”) ll)L.W6hIer & “Military Explosives” ,TM 9“1910(1955),60-4,97,
F. J. Roth,SS 29,9-11,46-8 & 74-7( 1934) (Bri- 106,109,113,123,126,133,1>9,153,158,163,167,
sance of initiating expls by Lead Plate Punch- 172,176,181-3,185,188-9,191,193,195,197,201,
ing Test) 1 la)L. Wohler & J. F. Roth,SS 298289 203,206 & 324( Brisance values and other expl
-72,331-4 & 365-8( 1935) and Ibid 30,11-14 & characteristics for many military expls) 28a)W.
39-42( 1935) (Discussion on methods of calcg E. Gordon et al,IEC 47,1799(1955) (Trauzl Test
and detg brisance) 12) T. Urbaiiski,SS3C),68 values for HMX,MeDINA,RDX, tetryl & TNT)
-71(1935) (Comparison of calcg brisance by 29)Cook(1958), 17 & 34 30)PATR 1740, Re-
Kast’s and Herlin’s formulas; detn of brisance vision 1(1958) (Expl characteristics fo US mili-
by Cu CyIinder Compression Test) 12a)J. tary expls) 30a)P ATR 1740, Suppl em ent NO 1
Hackel & T. Urba6ski,SS 30,98(1935 )( Brisance (1958) (Conf) (Not used as a source of info)
and other expl characteristics for various nitro- 31) D. Price, ChemRevs 59,801 -25(1959 )( Damage
starches) 13) A. Majrich & F. Sorm,SS 30,295-9 tests are a measure of expl performance and
& 337-40( 1935) (Calcn of brisance and detn by expl characteristics of Octol 70/25 and of some
Lead Plate Test and by Fragmentation Test) other HE’s) 32)H. A. Whetmore, “OctoI(HMX/
14)Pepin LehaHeut(1935),54 & 78 15) BeyIing TNT): A Literature Survey” ,Literature Search
& Drekopf( 1936),57-9 16)N.Sokolov, ‘Theory No 10,Tech Info Sectn, FREL,PicArsn, Dover,
of ExpIosives”,Gosi zdat,Moscow( 1937),3 14(in NJ(1960)(Conf) (Not used as a source of info)
Rus) 16a) M. Tonegutti,SS 32,93-7( 1937) (Bri- 33) W.H. Rinkenbach,Allentown,P a; private com-
sance & other expl characteristics for PETN, munication 196 1)
RDX & TNT) 17)R. R. Stadler,SS 33,338(1938)
(Brisance and other expl characteristics of Additional References on Brisance:
Ag acetYlide,MF,LA & LSt) 18)Davis(1943), A)L. H. Eriksen, “Study of Fundamental Properties
3 & 21O 18a) Blatt,0SRD 2014(1944) (Expl of High Explosive s’’,PATR 1192(1942)[Tests
characteristics for neatly all expls known were made to det if the claim is valid that the
before @II) 19)Vivas,Feigenspan & L adreda loading of different expls in layers results in
4(1944),58-62 & 118 20)P6rez Ara(1945), 117 the chge having a brisance value greater than
-18 21)G.M.Hopkins, PATR 1530( 1945) (Frag- the sum of the normal brisance values for the
raentation efficiency values for some military exp 1s. From resuIts of these tests, it was con-
expls) 22)D. R. MacDougaIl & E. H. Eyster, cluded that: a) While the max bris ante for a
“Physical Testing of Explosives” ,NDRC Div compound-detonator can be obtained when it is
8,1nterim Rept PT~34(1945),22(P lateDenting loaded so as to have each succeeding layer or
Values for 24 expls) 23) E. H. Eyster & D.P. layers initiated by an expl having a higher
McDougall, “Evaluation of Fivonite as a deton velocity, no evidence was obtained that
High Explosive’’,OSRD 5627( 1945), 11(P late a compound-deto na tor consisting of separate

1
 B 297

layers of different expls had ahigherbrisance According to Rinkenbach(Ref 3), there was
value than the sum of the max values for the developed at PicArsn the following approx
individual expls b)In the detonation of small empirical relationship between brisance(B) in
charges, as used in the Sand Test, the brisance grams of sand crushed by 0.4:g sample when
of TNT, tetryl and P ETN is dependent upon the detonated in a 200-g bomb, and detonation ve-
detonation velocity or brisance of the initiating locity (D) in m/see: logB = 3.45 log(D/2450). A
chge. Thus, TNT when initiated by tetryl or similar equation was later reported in a manual
PETN, gives brisance values higher than that compiled at Aberdeen PG(Ref 4)
obtained with hfF as the initiator of detonation] From sand test values (B) detd at PicArsn
B)H.Mu~aour & A. I?emay,CR223,278-80( 1946) & for ca 20 expls(using 0.4-g samples in both
BrA 1947,BI, 148; Ibid, Chim&Ind(P aris) 56, 463 200-g and 1700-g bombs) and from data available
-7( 1946) & BrA 1947,BI, 291 [The brisance of in the literature for their deton velocities (D)
MF and LSt(measured by tile size of perforation at approx their max densities, Rinkenbach
produced in a Ie ad plate) increased with com- obtained a nearly linear relationship on plotting
pression up to 8000 kg/cm2 when the e~ls B vs D. This permitted the following equations
were detonated with LA. The brisance of rnixts to be derived:
of some primary expIs was also increased on D = 63.99B + 4234 m/see- for 200-g bomb
supercompres sionl C)H.Muraour,Chim&Ind D = 76.76B + 3965 m/see- for 1700-g bomb
(Paris) 66,2803(1952) & BrA 1952, BII,439. The By means of these equations the deton vel of
views expressed by J. and J.13asset,CR 231, an expl can be caIcd with a mean accuracy of ca
1440( 1950) that the reduction in penetrating l 45 m/see
power of a shaped charge projectile when ro- Note: The above equations are not identical
tating, is due to compression of the explosive because the values for D obtained in the 1700-g
by centrifugal action and hence re suits in a bomb were somewhat lower than those obtained
decrease in brisance, are controverted. Com- for the same ezpls in the 200-g bomb; but the
pre ssion of a secondary expl, such as TNT, relative orders of the expls with respect to B
does not reduce but increases the velocity of were the same in both bombs. The difference
detonation and therefore the brisance. with betw the B values for each expl in the two
primary expls, such as MF, the problem is bombs is attributed to the different thicknesses
more complex. R-eduction in penetration of of the layers of sand betw the cap(contg the
rotating shaped charges is usually ascribed chge) and the walls of the two bombs
to displacement of the nose by centrifugal Table II gives a comparison between
action 1 D calcd by Rinkenbach and D obtained by aver-
(Note: It has been’ proven that reduction in aging the various values in the literature
penetration of rotated shaped-charges is due to
centrifugal action upon the jet itself. See SEE TABLE II ON NEXT PAGE
numerous APG and CIT reports) P)T.Sakurai, Jones & Sheffield(Ref 5) also discussed the re-
JIndExplosivesSocJapan 13,138-42( 1952); 14, lationship between brisance(as detd by the Sand
212-25(1953) and 16,90-4(1955); CA 49,5841 Test) and deton velocity but their data cannot be
( 1955); 49, 11283-4(1956) and 50, 17452(1956) included here because it is classified
(Discussion of various methods for measuring Re/s: l)H.Kast & A.Haid,ZAngewChem 38,5o-2
brisance) E)T.Sakurai,K5gy6 Kayaku Kyo>ai ( 1925) (Brief discussion on relationship betw bri-
Shi 18,41-9(1957); 18,22s-36(1957); 18,308-15 sance and detonation velocity for initiating expls:
& 369-73(1957) and 19,95-102, 181-92 & 236-40 cyanutic triazide, LA, LSt, MF and 90/10-MF/Kc103)
(1958); CA 51,9159 & 17167( 1957); 52,4987 2)T.Urbarlski,SS 30,68-71(1935) & CA 29,4941(1935)
(1958) and 53,9671( 1959) (Discussion of various [For expls such as TNT or AN expls, detonation
methods Tor measuring brisance) velocity may be, calcd from the equation D = (24.9Sp)~
where D is detonation velocity, S is compression of
Brisance·Detonation Velocity Relationship. It Cu cylinder in mm minus correcti~n O. 16mm (Com-
has long been recognized that brisance is re- pression produced by a No 8 cap), This relationship
lated to detonation velocity and efforts have does not hold for some chlorate expls] 3)W.H.
been made to determine and express relation- Rinkenbach, “Study Fundamental Properties of High
ship betn these two characteristics of an expl Explosives” ,PATR 1352(1943) [Relationship betw
~Refs 1 & 2 brisance(detd by sand tests in 200-g and 1700-g
 Toble II

Comparison of Detonation Velocities Calculated(from Sand Test Data) with those Published in the
Literature
Brisance,B, Detonation Velocity, D,m/sec
Explosive grams Sand Calcd by Taken from the Density,d,
Crushed in Rinkenbach Literature g/cc
1700-g Bomb

Pentaerythritol tetranitrate 57.9 8409 8350 1.67-1.70

(PETN)

Mannitol Hexanitrate 56.4 8294 8260 1.73

Cyclonite (RDX) 53.2 8049 8180 1.65

EthyIenedinitramine (EDNA) 48.4 7680 7620 1.5

Tetryl 47.7 7626 7680 1.60-1.71

Dinitroethyleneurea 45.0 7419 7660 1.6

Trinitrobenzene (TNB) 43.2 7282 7400 1.65

Picric Acid 41.8 7174 7300 1.63-1.71

Trinitroanisole (TNAns) 41.7 7166 7150 1.59-1,7

Trinitrotoluene (TNT) 41.2 7128 6970 1.60

Trimonite 39.9 7028 7020 1.60

Diazodinitrophenol (DADNPh) 39.7 7012 6900 1.58

Trinitroethylbenzene (TNEB) 36.3 6751 —

Trinitroxylene (TNX) 34.5 6613 6600 1.51

Ammonium Picrate (AP ) 33.7 6552 6775 1.55

AmatoI,40/60 33.4 6529 6470 1.54

Amatol,50/50 34.0 6575 6430 1.55

Dinitrobenzene (DNB) 23.6 5777 6100 1.56

Mercuric Fulminate (MF) 22.5 5669 5400 4.2

Lead Azide (LA) 18.6 5393 5300 4.6

Lead Styphnate (LSt) 10.9 4802 5200 2.9

 B 299

bombs) and detonation velocities] 4)All&Er@xpls (dent) made in the Fe plate by the crucible, by
(1946), 18[Brisance can be calcd with a small margin the amt of radial and concentric stratiation
of error by using the equation:LogB = 3.5 310@/2500), aro~d the dent and the amt of scaIing.
where B = grams of sand crushed by 0.4-g sample Sometimes the plate around the dent was colored
and D = deton velocity in m/see] 5)M.M.Jones & blue. Stettbacher claimed that the deeper the
O. E. Sheffield, “The Sand Bomb Test Considered as dent the more powerful was the expl and that the
a Fragmentation Problem” ,PATR 2424( 1957)( Conf) brissnce and detonation velocity may be approx
(Not used as a source of info) estimated by the appearance of the surface of the
plate. The deeper the blue color and the coarser,
Brisance Test Methods. Early test method s(begin- more numerous and deeper strati ations, the great-
ning in this century) for detg brisance included er was the bri sance and the higher was the deton
Lead Block Compression Test(LBCT) (Hess’ veIocity. The total energy was expressed in mm
method, also known as Austrian Method) and of depth of the dent
Copper Cylinder Compression Test(CCCT) Another method for measuring the brisance, the
(Kast’s Method, also known as German Method). so-called Stanzprobe (Punch Test), was developed
In the LBCT, a chge of expl(50 or 100g) is deto- in Germany and is described in Addnl Ref F. In
nated on a steeI plate covering a lead cylindrical this method the explosive was cast or pressed into
block 40-mm diam and 30-mm high. The resulting a seamIess steel tube which was centered vertically
compression of the block is measured and compared on a lead pIate placed over a pit or ‘shot hole*. The
with the compression produced on detonation of a expl chge, when initiated by a No 8 blasting cap
standard expl, such as TNT or PA. In the CCCT ~he and a booster chge of pressed PA, detonated and
compression of a copper cylinder(crusher) 7-mm punched a hole through the lead plate. The diam
diam and 10-mm high serves as a measure of bri- of the hole was a measure of brisance. According to
sance(Refs 1, la,3,3a,4,5,8,9,10, 10a, 11,14,15 & 16) to Dr Hans Walter, now at P ic atinny ArsenaI but
(See also under Compression Tests) formerly with the German Wehrmacht during WWII,
A modification of these tests, known as the when a highly brisant expl was tested it was
Quinan Test, is described in Vol l,p XXI of this sometimes the practice to force part of the chge
Encyclopedia and in Refs 6,9 & 13a beyond the end of the tube. This variation of
The Hopkinson Pressure Bar Method is briefly the test was used to measure the self-sustain-
described in Ref 7, Addrd Ref a and in Vol l,P ing detonation props of the expl when unconfined
XVI Th French methods for detg brissnce: “Epreuve
The methods currentIy used in the US include: des petits plombs” and “Epreuve de Chalon” wiIl
a)Sand Test(ST). It is described in Vol l,p XXI be described under Compression Tests
XXII and in Refs 4,17,18 & 19. According to some Re/s on Brisance Test Methods: l)N.W.Berger,SS
investigators this test measures the ‘energy of 1,150-2 & 169-72 (1906 )(Detn of brisance in Nor-
explosion” rather than brisance b)plate Denting way by Lead Block Compression Test and by
Test(PDT) and Plate Cutting Test(PCT). These Fragmentation Test) la)H.Kast,SS 8,88-9(1913)
tests are briefly described under Plate Tests in (Detn of brissrtce by Brisance Meter, which is also
Vol l,p XX(See also Refs 12,13,14,17 & 18) called Copper Cylinder Compression Test) 2)A.
c) Fragmentation Efficiency Test (.FET) is briefly Stettbacher,SS 11,249-50(1916); JSCI 36, 101(1917)
discussed as Fragmentation Test in Vol I,p XII & CA 11, 2733( 1917)(Detn of brisance and energy
(See aIso Refs 8,14,16,17& 18) by Iron Plate Denting Test) 3)Matshall 2(1917)
d) Fragment Velocity Test(FVT) is briefly (Detn of brisance by Brisance Meter) 4)C. E.
described in Vol l,p XIII(See also Ref 18) Munroe & J. E. Tiffany, “Physical Testing of Ex-
Stettbacher(Ref 2 & Ref 8,p 361) propc)sed a test plosives”,USBurMine s,Bull 346(193 1), 106-15
which was c1 aimed to det simultaneously brisance (Detn of brisance by SmalI Lead Blocks Test,
and energy. In this method, known as StrabIungs- by Sand Test and by Nail Test) 5)Sukharevsky
probe (Radi ation Test), a finely powdered expl & Pershakov( 1932), 120- I & 126(Detn of brisance
(ca 50g), packed lightly in a thick Fe or Ni by Sand Test and by Cu & Pb Compression Tests)
crucible, was placed in the center of a square 6)Vennin,Burlot & L6corch6 (1932), 192-3(Detn
?Iate of soft Fe, 6.8mm thick, supported on the of brisance by Quinan apparatus) 7)MarshalI 3
:op of a hollow cylinder. After initiating the expl (1932) (Detn of brisance by Hopkinson’s Pressure
>y means of l-2g MF-LA mixt, the detonating Bar Method) 8)Stettbacher( 1933),50-I, 361 & 365-7
:ffect was measured by the depth of impression (Detn of brisance by Fragmentation Test, Lead
 I

Block Compression Test and Copper Cylinder TNT 55.O(d 1.55, cast), .PA 54.0( 1.6,cast, tetryl
Compression Test) 9)Pepin Lehalleur( 1935 ),63-4 57.8( l.55,pressed), m-TNX 43.7(1.45), m-!lNB 32.9
& 78(Detn of brisance by various methods) 9a)A. (!L2), 2,4-DNT 31. 1(1.2), DNN(crude) 14.1( 1.2)&
Majrich & F. Sorm,SS 30,295-9& 337-40(1935) MNB 4.0(1. 18, liq~ B)L.Wohler & F. J. Roth,SS
(Detn of brisance by Fragmentation Test and by 29,9-11, 46-8 & 74-7( 1934); CA 28,3901-2( 1934)
other methods) 10) Beyling & Drekopf(1936),645 (objections to existing methods of calcg brisance
(1936) (Detn of brisance by Cu Cylinder Compres- and to detg it by compression, of Cu or Pb cylinders
sion Test) 10a)Reilly( 1938 ),68( ?3rief description are cited. A new method for detg brisance is de-
of Kast’s Brisance Meter) 1 l)Meyer( 1943),37 5(Detn scribed in which 0.6g of a mixt of NaCl with an
of brisance by Lead BIock Compression Test) insensitive expl such as TNX is interposed betw
12)Vivas,Feigenspan & Ladreda 4(1944), 118-20 the chge of expl to be tested and a 4-mm Pb plate.
(Detn of brisance by Plate Cutting Test) 13)L.C. The chge is pressed into a piece of Cu tubing [35
Smith et al,OSRD 5746( 1945),20- 2(Detn of brisance or 50mm long & 7mm ID, with lmm wall; and det-
by P1 ate Denting Test) 13a)P6rez Ara(1945), 118 onated by a suitable initiator. The effect on the
(Quinan Test) 14)Stettbacher( 1948),89-90,99, 110 Pb plate is dampened by the intervening layer
& 114-17 (Detn of brisance by PI ate Denting Test, of NaC1/TNX mixt to an extent depending on its
Copper Cylinder Compression Test and by Frag- percentage content of NaCl which is varied until
mentation Test) 15)Belgrano( 1952),39-4 l(Detn the effect just produces a clean cylindrical per-
of brisance by Lead Block Compression Test) foration in the plate. The results of testing 24
16)Stettbacher( 1952), 113- 19,141-2 & 146-9( Various expls are tabulated) C)L. Wohler & J. F. Roth,SS
tests for detg brisance) 17) Anon, “Military Ex- 30, 12-13(1935) (Method for detg the brisance of
plosives”,TM 9*1910( 1955),60-5 (Detn of brisance liquid and plastic expls, using the lead plate)
by Sand Test, Plate Denting Test and Fragmenta- D)T,Urbaiiski, SS 30,68-7 1( 1935) & CA 29,4941( 1935)
tion Test) 18)P ATR 1740,Revision 1(1958) (Brief (1935) (Detn of bris ante by a modified Kast
description of Sand Test, Plate Denting Test, Copper Cylinder Compression Test method using
Fragmentation Test and Fragment Velocity Test) 7 x lo-mm Cu cylinders and omitting lead plates)
18a)T.Sakurai,JIndExplsSoc(Japan) 19, 181-92 & E)E.Calvet,AnnF acult.4SciMarseille 16,3-13( 1942)
236-40( 1958); 20,57-65(1951) (Brisance tests) & CA 41,2575-7 (1947 )( Determination of brisance
19)A. J .Clear, “Standard Laboratory Procedures for by meams of a special apparatus. The values, B,
Sensitivity, Brisance and Stability of Explosives”, detd by this method were TNT 44, PA 47, tetryl
PATR FRL*TR*25( 1961), 24(Detn of brisance by 61 & RDX 77) F)P.Nao6m & A. Berthmann, “Ex-
Sand Test) [This report is a revision of PATR plosivstoffe” ,p 373 in Vol II of Chemische Techno-
1401( 1944), compiled by W’.H.Rinkenbach, and of logie”(Organische Technologies II) by K. Winnaker
1401, Revision 1( 1950] & E. Weingaertner,Carl Hanser Verlag,Miinchen
Additional Re{s on Brisance Test” Methods: (1954) [Detn of brisance by Stanzprobe(Punch
A) R. Robert son,JCS 119, 19-24(192 I)[The usual Test) der Chemisch-Technischen Reichsanstalt
methods for measuring brisance(such as listed {Berlin)]
above) are considered inadequate and the method
known as Hopkinson’s Pressure Bar is proposed. Briska Detonator(Briska Kapsel in Ger). A brief
In this method it is possible to det the blow or description is given in PATR 251O(PB Rpt 161270
pressure developed by an expl over a small measur- (1958), p Ger 23. Briska caps No 6 & No 8 have
able interval of time and this is a measure of the been used bY the British[See also Taylor(1952), 111
violence(bris ante) it exhibits. The principle on
which the determination of the pressure is based Britainite. An expl invented by Von Dahmen con-
depends on the fact that when a chge is fired sisted of AN 70.8, KN03 & KC103 20.4, naphthalene
against the end of a cylindrical steel bar, bal- 7.1 & moisture 1.7%
listically suspended, a wave of compression Refi Daniel(1902),83
travels along the bar and is reflected at the far end
as a wave of tension. For details of measuring British Ammanals. See under British MiIitary Ex-
pressure by this method see B. Hopkinson,PhilTrans plosives and under Ammonals, VOI l,pp A289,
213A,437(19 14) and Vol 1 of this Encyclopedia, A290 & A291-R
p XVI. Following are results of tests by this
.2. British Ammonium Nitrate Dynamites. See Vol l,p
method expressed as pressure in tons per In in
().5 x 10-5 sec(with constant pellet interposed): A368(table)
 6301

British Commercial Explosives. Advances in Explosive). See CyclotetramethyIenetewanitramine

British coml HE’s is discussed in detail by Taylor Lead Azide(LA). Used in friction primers(mixts
(Ref 1). See aIso Ref 2, British Arnmonals in Vol of LA/Sb$3/KC103/Abrasive) and in detonators
l,pp A289, A290 & A291-R and British Ammonium (in conjunction with LSt) (Ref I,p 68)
Nitrate Gelatin Dynamites in Vol l,p A368(table) Lead Sty@nate(LSt). Used in conjunction with LA
Re/: l) J. Taylor, Research(London) 1947,67-76(a in detonat ors(Ref I,p 70)
review with 59 refs) & CA 42,2105( 1948) 2) Taylor Lyddite. Brit designation for cast Picric Acid
& Gay(1958),l-50 & 86-1o6 Merc~ric Fuimirr.ate(MF). lJsed in the following
primer mixts: a)”A= mixture MF 25, KC103
BRITISH MILITARY EXPLOSIVES AND PROP EL- 58.3 & Sbzss 16.7% b)”B” mixture MF 11, KCIO~
LANTS. Following list includes Brit expls and 52.5 & Sb#9 36.5% c)”C’ mixture MF 32, KCIO~
prophts, some of them obsolete: 45 & Sb.$3 23% d)”D= mixtute MF 60 & KC103
Abel’s Explosive. See Abel Powder or Picric Pow- 40%(Ref l,p 64)
der in Vol l,p Al-R M inol 11 (TNT/AN/Al-40/40/20). Used in sea mines,
Alurnatol. See Vol l,p A 141-R depth charges and A/S & HC bombs(Ref I,pp 85-6)
Arnatex 9. See Vol l,p A157-R Nobel’s 704( AN/TNT/Al-69/ 15/16. Used in gran-
Amato!s. See Vol I,p 162-R ades(Ref l,pp 84 & 86)
Arnmonals. Used in demolition and cratering charg- Nob cl’s 808. No info on its compn at out disposal.
es. Their compns included: a)AN 65, TNT 15, AI Used in some bombs
17 & charcoal 3% b)AN 65, TNT 15, Al 10 & PE-2 (Plastic Explosive-2). Same as Amer Com-
charcoal 10% (Ref l,p 84)( See also VOI l,p A261 position C
-R & Ref 2,p 26) P entbrite(PE TN). Used as the core in Cordtex
Note: Brit expls Alumatol, Burtowite, Minols and Detonating Fuse(Ref l,pp 135-6)
Nobel’s 704 also belong to the class of expls Pentolite (PETN 50 & TNT 50%). Used as burst-
known as Ammonals ing chge in MC & Fragn bombs, A/P mines and
Baratol: The compn contg TNT 90 & Ba nitrate 40-mm shells(Ref l,pp 138-9)
10% was used in A/T mines, grenades & A/S Picric Acid(PA). Used in boosters (pressed) ard
bombs(Ref I,p 89)( See also Baratol in this vol) in grenades & some shell s(cast, under the name
Black. Powder. See this volume Lyddite)
Burrowite. One of the Brit Ammonals(See also Picric Powder. Same as Abel’s Explosive
Burrowite in this vol) RDX (Research Department Explosive) (Cyclonite).
CE(Composition Exploding) (Tetryl). Used in Used in Composition A, Composition B, DBX,
standard boo sters and as bursting chge in them P E-z, RDX/’DNB mixture & Totpex(See aIso Cyclo-
ammo(Ref I,pp 91 & 93) trimethylenetrinitramine)
Composition A(RDX/Beeswax-9 1/9). Used as RDX/D N3-60/40 Mixture. Lt ye] cast expl with
filler for some shells & grenades(Ref l,pp 12 I-2) characteristics intermediate betw TNT & Comp
Composition B. See under Cyclotol B and about as sens as PA. Its specific use was
Cordite. Brit standard propellant(see Cotdite) not stated but it could have been used as a burst-
Cyclonite. See RDX ing chge(Ref l,p 135)
Cyclotol. Mixts of RDX 50 or 60 & TNT 50 or Sh ellite [called in the US 70/30 Tridite(P A/DNPh
40%. The mixt RDX/TNT/Wax-59/40/l is called -70/30)]. Used as the bursting chge in AP bombs
Composition B in the US and RDX/TNT-60/40, and sheIls(Ref l,pp 99-100)
Composition B 2. Cyclotols were used by the Brit Tetryl (US). See CE (Composition Exploding)
as bursting chges in GP, MC, HC, A/S, Fragn & Tetrytol (Tetryl/TNT-75/25). Used as bursting
Parachute bombs and in some shell s(Ref l,pp chge in some bombs and as a booster chge(with
1234) the addn of wood meaI to decrease the density
DNB/RDX Mixture. See RDX/DNB-60/40 Mixture and thereby increase the sensitivity) (Ref l,p 94)
DBX (Depth Bomb Explosive) (RDX/AN/TNT/Al- TNT. See Ttotyl
-21/21/40/18). Used as a bursting chge in depth Torpex I (RDX/TNT/AI-45/37 \18 or RDX/TNT/Al/
bombs(Ref l,p 130) Beeswax-44/37/18/l) and Torpex II (RDX/TNT/
Guncotton Explosive. NC(ca 13%N), contg ca 13% A1-42/40/18). Used in MC & A/S bombs, aerial &
H20. Used in l-lb demolition blocks(Ref l,P 149) submarine torpedoes and in rockets{Ref l,PP 128-9)
HMX (His Majesty’s Explosive or High Melting Tridite. See SheHite
 I

Trinitrotoluene. See Trotyl temp at which a compd or compn becomes too

Tritonal (US). See UWE brittle to be used for specific purposes. This
Trotyl (TNT). Used as bursting chge in GP, MC, prop is of particular importance in inst antes
SAP, A/S & Fgran bombs; in land mines, rockets, where proplnts, plastic expls, rocket or J A TO
aerial torpedoes and shells of all types(Ref l,p chges are intended for use or storage in colder
75) climates such as Alaska, Northern Canada or
UWE (Underwater Explosive) (TNT/Al-80/20). Siberia
Used in lieu of Minol II as bursting chge for Many methods for testing the brittleness of
4000-lb HC bombs(Ref l,p 88) and considered for materials such as plastics & rubbers were pro-
use as an underwater expIosive posed, among them: a)Bent Loop Test(Ref 1)
Abbreviations: A/? antipersonnel, A? armor-pierc- b)Bell Telephone Laboratory Test(Refs 2,3 & 4)
ing, A/S antisubmarine, A/T antitank, Fra~n frag- c)Swinging pendulum Test(Refs 5 & 11) d)Du-
mentation, GP general purpose, HC high capacity, Pont Co Te st(Ref 6) e) Charpy Tesr and f)Izod
MC medium capacity and SAP semi-armor-piercing Test(Ref 7). None of these methods seems to be
Re/s: l) AII&EnExpls( 1946) 2)Taylor & Gay very reliable except the method developed at the
(1958),26 Bell Telephone Lab(Ref 4). It was tentatively
adopted in 1943, by the ASTM as the D476-43T
British Propellants. See Cordites Test and later modified, to be known as D476
-57 T(Ref 12). This test was adopted by the US
British Tests. See Physical Tests for Determining Govt for testing organic plastics and is incorpo-
Explosive and Other Properties Vol 1 and specifi- rated in Federal Specification L-P-406 b(Ref 13).
cally the following British tests: a)Ballistic In this procedure, a specimen(such as a strip of
Pendulum Test, p VII; b) Exudation(or sweating) plastic, hard rubber, propellant, etc), 1“ long,
Tests, p XI; c)FI Test(F igure of Insensitiveness 0.25” wide and 0.07s” thick, is placed in a low
Test); p XII Fragrnen t Gun, p XII; d) Friction -temp bath where it is brought to the desired
Sensitivity Tests, p XIII; e)Hopkinsorz’s Pres- temp of testing. The sample is then clamped in
sure Bar Test, p XVI; and f)Silvered Vessel Test a special apparatus and subjected to an impact
or Waltbam Abbey Silver Vessel Test, p XXIV of a striker, which can be either motor-driven or
actuated by a solenoid. If the specimen breaks,
British Weapons. No information at our disposal the test is repeated at higher temps until no fail-
ures occur in 5 out of 10 tests. This method has
Bri tonites. Brit coal-mine expls manufd after WWI been used for detg the brirtle point of some pro-
by the British Explosives Syndicate, Ltd,Pitsea. pellants, such as Aerojet, Arcite 101, JpN,
They used to be on Permitted List, but have now Thiocol, etc, but the results of these tests are
been repealed. The original compn contained NG classified
26, K nitrate 32.7, woodmeal 41 & Na carbonate A different method was used at NOTS, China
0.3%. Later compns were: N02, which contained Lake, Calif(Ref 8) for testing double-base
NG 24, K nitrate 30, woodmeal 38 & Amm oxalate proplnts, but the re suits are also classified.
(cooling agent) 8% and N03, which contained NG The same may be said about testing the brittle-
24.5, Na Nitrate 28, woodmeal 35.5 & NaCl 12%. ness of ball powder at Frankford Arsenal, Phila
Power(swing of ballistic pendulum) was 2.26” (Ref 10). Brittleness of some proplnts was detd
for No 2 and 2.17” for No 3, vs 3.27 for std at PicArsn by the compression method(Ref 9)
Gelignite. Limit charge for borh No 2 & No 3 but these results are classified
was 240z Re/s: l)S.M.Martin,Jr, Rubber Age(NY) 52,227
Re/s: l) Marshall ](1917),376 2)A.Marshall, ( 1942) (A bent-loop test, incorporated later by
“Dictionary of Explosives” ,Chutchill,Lonclon ASTM as D736-43T) 2)hi.L.Selker et al,IEC
(1920),15-16 34, 157-60( 1942)(A simple app in which a
specimen, in the form of a strip attached to a
Britonite. A mixt of K nirrates,Amm oxalate, NG movable shaft, sharply strikes a stationary
& woodflour steel arm) 3)A.R.Kemp et al,IEC 35488(1943)
Refi Cond Chem Dict( 1942), 288(not found in later (Modification of the previous app by fitting it
editions) with an electric ,motor and a set of gears in an
attempt to control the rate at which the sample
8rittle Point or Brittleness Temperature. The strikes the arm) 4)R. E, Morris et al,IEC 35,

1
 B 303

864(1943) (Further modification of Selker ~d Bromates. The salts of bromic acid contg the
Kemp methods to give better control of temp monovalent radical ‘Br03. These salts are
and higher velocities at point of impact) 5)C.K. generally considered to be more toxic than
Chatten et al, Rubber Age(NY) 54,429( 1944)(A chlorates, causing central nervous system
test device in which a swinging pendulum im- paralysis. They form metahemaglobin, but less
parts a blow to the specimen) 6)H.G.Bimmerman actively than chlorates. Bromates in rh e form
& W.N. Keen, of the DuPont Co, IEC,AnalEd 16, of gas, vapor or dust represent mod fire haz-
588-90( 1944) (An w using alternating current ard. They are powerful oxidg agents and react
solenoid as a source of power permits control with oxidizable(reducing) materials more or
of the velocity of the device inducing the de- less violently, very often causi combustion
formation) 7)G.S.Brady, ” Materials Handbook”, (Ref 4). Props of the more impo. ant bromates
McGraw-Hill, NY(1951),852-3(A brief description are described by Mellor(Ref 3), Sax(Ref 4) and
of the Charpy & Izod methods) 8)J .M.Nielsen others:
& F. M. Ernsberger,’ ‘Some Factors Affecting
Brittle Temperatures of Double-Base Propellants’~
NAVORD Rept 2034,NOTS 708(1953) (Conf) Aluminum B inmate, Al(BaO~)3“9H20, mw
9)E.McAbee, “Applied Research on Rocket Pro- 572.% CrYSCS, mp 62.3°, bp dec(Ref 4,P 260
peHants-Test Methods-Mechanical Properties”, Ammonium Bromate, NH4Br03, mw 145.96;
PicArsnTechRept No 1979(1953) (Conf) 10)W.F. CO1aysts, mp expl(Ref 4,P 275)
Ashly, ‘‘ Brittle Fracture of Bali Propellant”, Barium Bromate, Ba(BrO~)2”H20, mw 411.21;
Frankford Arsenal Rept No F&l 360, Philadelphia, wh crysrs, mp 260°(dec) (Refs 3a*p 64% 4*P
Pa(1956) (Conf) 11 )J.P.Frankel, ‘Principles of 330 & 6,P 125)
the Properties of Material s“ ,McGraw-Hill,NY Cadmium Bromute, Cd(BrO~)2”H20, mw 386.3;
(1957),184-5(A brief description Of a Swinging CO1rhmb trysts, mp dec:powerful oxidizer
Pendulum Method for testing brittleness) 12) (Refs 4,p 418 & 6,193)
12)ASTM Standards,part 9, Philadelphia, Pa(1958), Calcium Bromate, Ca(Br03)2”H20, mw 386.3;
PP 355-60 13)US Feder~ Specification L-P monocl trysts, mp 180° (loses w of crystn)
-406b),Method 2051 (Ref 4,p 425)
Cupric B rvmate, CU(BX’Oa)2•6 H30, mw 427o5;
BRL=l.NC-polyester urethane, high performance bl-grn cubic trysts, mp dec 180 & 200° (loses
solid proplnt system described by Davis & Lenk w of crysm)(Ref 4,P 515)
(Ref) Lead Brornate, Pb(BtOs)2’H20, mw 481.1;
Re/: K. E. Davis & C. T. Lenk,Wyrmdotte Chem monocl trysts, mp d ec 180°(Refs 4,p 816 &
Corp Tech Note, Contract DA-20-O 18-0~-13364, 6, p 657)
1 Aug 1958 to 1 Aug 1959(Conf) Mercuric Bromate, Hg(Br03)2”2 HZO, mw 492.3;
trysts, mp dec 130-140°, highly toxic(Ref 4,p
Broberg and Wil drick of Dover, NJ,USA, ~ atented 856)
in 1895 expls contg NsN03 40 to 80, nitronaph- Mercurous Bromate, Hg2(Br03)2, mw 657*1;
thalene 10 to 20, sulfur 5 to 12, KC103 1 to trysts, mp dec, highly toxic (Ref z&p 865)
15% & nitrated resin (amt not specified) Nickel Bromate, Ni(Br03)~6H20, mw 422.6;
Ref: Daniel(1902),84 monocl trysts, mp dec(Ref 4,P 933)
Potassium Brumate, KBr03, mw 167.0; wh
Brockite.A mixt of Al & Ba chlorate trysts, mp 434° dec at 370 °(Refs 4*P 1037 &
Refi CondChmDict( 1942), 288(not found in later 6,P 926)
editions)
 B 304

Silver Bromate, AgBr03, mw 235.8; wh powd. and may also be highly toxic. The irritant
mp dec(Ref 4,p 1103 & 6,p 1022) effect is more violent if the halogen is sub-
Sodium Bromate, Na Br03, mw 150.9; wh trysts, stituted for O and directly bound with the As
mp 381 °(Refs 3a,p 649; 4,P 1113 & 6,P 1036) atom. Wachtel(Ref l,p 191) lists as fatal the
(See also Refs 4a & 5) following bromides in concns over 3000 mg/m3:
Strontium Bromate, St(Br09)2”H20, mw 361.5; dimethylarsinebrom ide[(CH3)2= As-Br]; diphenyl.
col-yel monocl hygr trysts, mp 120°(loses w arsinebromide, [(C6H5 )2. As-Br];o-chlorophenyl-
of crystn), bp dec 240°(Refs 4,p 1138 & 6,p pbenylarsinebromide,C6H~ A s-~r,
1080) CI.C6H4’ ‘
Zinc Bromate, Zn(Br03)2”6H20, mw 429.3; wh methylarsinedib romide, CH3 - As= Br2; ethyl-
delq powd, mp 100°, bp 200 °(loses w of crystn) arsinedibromide, C2H~-AsBr2; phenylarsine.
(Ref 4,p 1267) dibromide, C6H~ -As= Br2 & arsenic tribromide,
Junk(Ref 1) found that K Iwomate, present as As= Br3(Ref 4)
an impurity in KC103 prepd by the electrolytic Nitrosyl bromide, NOBr, mw 109.92; brn gas or
method, may cause spontaneous ignition on dk-brn liq, fr p -55.5°, bp -2°C; formed by
contact with combustible materials. Small amts passing NO into bromine at -15°(at RT NOBr3 is
of KBr03, up to 0.1 5%, are permissible in KC103. formed)(Ref 1). According to Sax(Ref 4), this
Main(Ref 2) patented a detong compn composed compd is severely toxic since single exposure
of MF 70-95 & a bromate, such as KBr03, 5-70%; can cause injury or mucous membrarie sufficiently
and claimed the bromate gave a higher detong serious to threaten life or cause physical
force than a similar mixt contg chlorate. Marshall impairment
(Ref 2a) claimed that KBr03 has a harmful Seel et al(Ref 3) have studied the reaction
effect on the stability of expls of NOBr with iodides & with azides. The
Re/s: l)A.Junk,SS 8,412-4 & 430-2(1913) & CA reaction with iodies in S02: 2NOBr + 21-a 2N0 +
8,421(1914) 2)W.L.Main,U.SP 1147958(1915) & 12+ 2Br-, provides a basis for detecting & detg
CA 9,2592(1915) 2a)Marshall 2(1917),689 the amt of nitrosyl halide
3)Mellor 2(1922 ),338ff 3a)Kirk & Othmer 2 Re/s: l)C.Wachtel, ‘ ‘Chemical Warfare”,
(1948),649 4)Sax(1957),381 4a)S.Kay,PATR ChemPublgCo, Brooklyn, NY(1941), 185 & 191
1947(1957) (hrhy detd by ti~ation in non 1 a)Kirk & Othmer 2(1948), 646-7 2) Partington
-aqueous medium) 5)USSpec MIL-S-1 1173 (1950), 322 & 558 3)F.Seel et al, ZAnorgChem
6)CondChemDict( 1961),193,926 & 1036 264, 298 & 311(1951) & CA 46, 6984(1952)
3)Sax(1957), 316( for AsBr3), 330(for BaBr2),
382( for bromides)& 959(for NOBr)
Bromazide. See Bromine Azide, Vol l,p A525-R
Brominated Nitroparaffins. Some of these compds,
Bromides. Binary salts contg negative monovalent contg both Br and N02 groups$ are expl. The
bromine. They are usually soluble in w. Accord- following are typical examples:
ing to Sax(Ref 4)$ the most common inorg Saks Potassium Bromodinitromethane, KCBr(N02 )2,
are sodium, potassium, ammonium, calcium & yel, triclinic trysts, d 1.25 at 20°, easily SO1 in
magnesium bromides. When ingested or inhaled hot w, diffc sol in cold w; insol in alc & eth;
the inorg bromides produce depression, emanci a- expl at 145-164 °(Ref 1). The existance of the
tion and, in severe cases, psychosis and mental monohydrate, KClBr{N02 )2. H20, was reported but
deterioration. Bromide rashes(wbromoderma”), not confirmed
esp of the face and resembling acne and furun- Silver Bmmodinitromethane, AgCBr(N02)2,
culosis, often occur when bromide inhalation golden yel, shiny trysts, prepd by the action of
or administration is prolonged. The most AgN03 on potassium bromodinitromethane;
common org bromides, methyl & ethyl bromides, expl on heating(Ref 1)
are vol liquids of rel high toxicity Dibromodinitromethane, Br2C(NOz)2, heavy yel
According to Wachtel(Ref 1,P 185), the org oil, mp 7.4°, bp 78-80° at 19mm, 86° at 23mm,
arsine compounds will possibly belong among d 2.395 25°/40, n~ 1,522 at 20°; may be prepd
the most efficient war gases in future wars. by methods given in Ref 2; expl at 158°
If the place of O in compds of the type R-As= O Brornotrinitromet bane, BrC(N02)3, fr p 17-18°,
is taken by halogens and other radicals, the re- bp 56° at 10mm, d 2.044 at 15/4° S1 sol in w; may
sulting compds are extremely violent irritants be prepd by methods given in Ref 3; expl on
 B 305

heating to a very limited extent, in France(’‘Sulvanite” ) &

Refs: l)Beil 1, 78 & [44] 2)Beil 1, 79, (21)& in Germany (” Brom’’) as a CWA(Ref 4)
[44] 3)Beil 1,79, (21)& [46] Refs: l)Mellor 2(1922), 90, 101 & 105; Suppl 2,
Pt 1(1956), 689-723 2)GmeIin, Syst Nr 7(1931),
Brominating Agents; Danger of Explosion. 34-166 3)Thorpe 2(1938), 106-16 4)Wachtel
Solid brominating agents should be investigated, (1941), 142 & 154 5)Hackh’s(1944), 144 6)Kirk
with regard to their expl hazard, on a small & Othmer 2(1948), 629-45 7)Partington(1950),
scale$ before they are recommended for industrial 317-19 8)Faith, Keyes & Clark(1950), 143-8 &
use on a larger scale. For example, when tri-N 2nd ed(1957), 165-70 9)Sax(1957), 382
- bromomelamine was added to allyl ale, the
mkt. exploded after 15min at RT bromine Azide. See Vol lip A525-R
Ref: J. A.Vona & P. C.hierker, C & EN 30,
1916(1952) & CA 46, 7329(1952) Sromine Azidodithiocarbonate. See Vol l,p
A635-R
Brominotion of Phenols was studied by G. Heller
et al. Some of the products obtained during Bromine Chloride, BrCl, mw 115.37; red-yel liq
these investigations were expl or gas} bp 10°(dec); according to Partington
[See also 3,5,6-Trinitro-2 -aminophenol and its (Ref 2), Cl merely dissolves in Iiq Br and no
brominated product(Vol 1,p A244-L under compd(BrCl) has been obtd in the pure state$
Aminophenols)] although from spectroscopic evidence BrCl
Re/: G.Heller et al, JPraktChem 129, 211-56 appears to exist to some extent in a mixt of Cl &
(1931) &CA 25, 2128-9(1931) Br vapors. }lackh’s(Ref 1) lists the compd as
BrCl~10H20, yel trysts or liq, mp 7°(dec~ v sol
&omine(Brom in Ger & Rus$ Brome in Fr~ Bromo in w, CS2 or eth. Sax(Ref 4) c~nsiders BrCl a
in Ital & Span), Br, at wt 79.92; dk-red fuming very powerful oxidg agent which is dangerous
Iiq or rhomb trysts, fr p -7.3°, bp 58.7°, d 2.93 when heated to decompn because it emits
at 59° & 3.12 at 20°; vap press 175mrn at 21° & highly toxi~ fumes of Br & Cl; it is a mod fire
latm at 58.2°, vap d 5.5; sol in ale, chlf, eth & W. hazard, reacting vigorously on contact with
Elementary bromine never occurs in nature but reducing materials. The physiochemical props
is found mainly as bromides of alk metals, in of this and other interhalogen compds are
natural waters, brines & sea water. Bromine reviewed by Greenwood(Ref 3)
was discovered in 1826 by A.J .Balard in the Re/s: l)Hackh’s(1944), 144 2)Partington(1950),
mother liquors of sea water> and named from the 325 3)N.N.Greenwood, RevsPureAppliedChem
Greek “Bromos”, meaning stench(Refs 1,2,3,5, (Australia) 1, 84-1? 0(1951) & CA 46, 2356(1952)
& 6). It can be prepd in the lab by heating K 4)Sax(1957), 383
bromide with dil }12S04 & Mn02 in a retort;
prepd technically from Stassfurr or other Bromine Dioxide. See under Bromine Oxides
bromides by passing chlorine & steam into
the soln in a tower packed with porcelain(Ref 7), Bromine Fluorides. The following compds are
Bromine is a very powerful oxidg agent described in the literature: Bromine mono fluoride,
The toxicological action of Br is essentially BrF, mw 98.92, red-brn unstable gas, fr p -33°,
the same as that of Clj being an irritant to the bp 20°; is formed from the trifluoride & bromine
mucous membranes of the eyes and the upper (Ref 2). Bromine trifluoride, 13rF3, mw 136.92,
respiratory tract. Severe exposure may result in coI to gray-yel liq, fr p 8.8°, bp 135°> d 2.49 at
pulmonary endema. Chronic exposure is similar 135°; is formed from fluorine and bromine or HBr
to the therapeutic ingestion of excessive bromides (Ref 2). Bromine pentafluoride, BrF5, mw 174,92,
(qv). The MAC(max allowable concn) is 6.5mg/ma CO1 liq, fr p -61.3°$ bp 40.5°, d 2.47 at 25°, vap
of air or lppm in air(Ref 9) d 6.05; is formed from the elements at OO(Ref 2).
It is used for the separation of minerals Sax(Ref 3) considers these compds to be
(for example, gold extraction), in making dyes, dangerous when heated to decompn or on contact
and as a local anesthetic, antispasmodic d with an acid or acid fumes, since they emit
sedative medicine. It is also used to some extent highly toxic fumes of bromine & fluorine; they
as a disinfectant, absorbed in sticks of diatomite react with w or steam to produce heat, toxic and
brick(Refs 7 & 9). Bromine was used during WWI, corrosive fumes
 B 306

Sharpe & Emel~us(Ref 1) have studied the & Townend(Ref 2) by passing bromine vapor over
reaction of bromine triiluoride, with many pprd HgO(Ref 3). Bromine dioxide, Br02, mw
metallic halides and other compds. These 111 .92; lt-yel crpts, mp OO(dec); prepd by the
investigators found that BrF3 reacts violently action of an elec discharge on a mixt of bromine
with K13rj KI & CC14 and explosively with vapor and excess O in a strongly cooled tube
acetone, dioxane, silicone vacuum grease, (Ref 3). Pflugmacher et aI(Ref 4) detd the Qf of
NI{4F & NH4C1. An excess of BrF3 converts Br02 as -12.5 ~ 0.7 kcal/mol from the reaction
the chlorides of K, Ag & Ba into the correspond- Br02(solid) +1/2Br2 + 02. The Br02 was kept
ing bromofluorides( bromotetrafluorides) Ki3rF4, at -40°$ where it was stablej and then transferred
AgBrF4 & Ba(BrF4)2. The K compd does not to a calorimeter at 20°$ where it decomposed
react with or dissolve in CC14, acet or dioxan e$ explosively. Pflugmacher(Ref 5) also obtd
whereas the Ag and Ba compds do not react with trinitrobrornine dioxide, Br02 .3N02, a wh solid
CC14 but ignite eth, acet, dioxane & gasoline stable up to -50°, which slowly decomposes at
l?e~s: l)A.G.Sharpe & H. J. Emel@ JCS 1948, .400 to Br02 & Noz on passing a mixt of OZ ~
2135-8 & CA 43, 3739(1949) 2)Partington(1950), N2 & Br2 through a glow discharge at liq-air
341 3)Sax(1957), 384 temp and low press or from Br02 and N02 at
-40°. It decomps in w and bases, reacts with
Bromine Hydrate, Br2.101120, mw 340.o; red benz or eth and gives solns in CHC13 or acet
crysts$ mp 6.8 °(dec); is formed if satd bromine stable up to -30°. Bromine trioxide, Br03, mw
water is cooled in a freezing mixt in the 127.92; wh trysts, mp dec above -70°; prepd by
presence of Br2(Ref 4). The structure of this the reaction of Br2 with a 50-fold excess of 02
and other bromine hydrares has been the subject in a glow discharge at OO(Ref 6). It gave CO1 aq
of many investigations. Hackh’ s(Ref 1) lists solns contg Br03”; solns in MeOH or acet were
this compd as Br.101-!20, red octahedric trysts, also CO1 at first$ then turned yel or red on
dec 1.5°; Stackelberg et al(Ref 2) and heating above -80°. The Br03 was sometimes
P artington(Ref 4) give Br2.8H20; Claussen produced mixed with BrOz; addn compds may
(Ref 5) and hfiiller & Stackelberg(Ref 7) give exist. Bromine octaoxide, Br308~ mw 367.15;
Br2.72/3 H20; and Zernike et al(Ref 6) give wh crysts$ mp stable at -80°(Ref 3) to -40°
the solid compd Br2.7H2C), mp 5.85 °(dec).Stackel- (Refs 1 & 7); exists in two modifns with a
berg(Ref 3) has reviewed the structure, props, transition point at -35°. It is prepd by the action
constitution, heat of form and other props of the of pure(100%) 03 on purified Br vapor at -5 to
gas hydrates. Sax(Ref 8) lists bromine hydrate + 10° under low press(Ref 1). Only by keeping
(Br2.JO}!20) as a strong oxidg agent which is the temp of reaction low, carefully avoiding too
dangerous when heated to decompn, emitting much ozone or bromine, using very pure materials
highly toxic fumes of bromine and, on contact and a very clean appar can expln be avoided(Refs
with water or steam & reducing marerials~ it 1 & 3). This oxide is sol in w forming a CO1 soln
can react vigorously contg no free Br. It is unstable in the presence
Refs: l)Hackh’s(1944), 144 2)M. v. Stackelberg of 03
et al, Forts chrhfineral 26, 122-4 (1947 )(publd in Sax(Ref 7) considers the bromine oxides
1950) & CA 44, 9846(1950) 3)M. v ,Stackelberg, to be strong oxidg agents, representing mod
Naturwissenschaften 36, 327-33 & 359-62( 1949) & fire hazard in the vapor state or by them reaction
CA 44, 7107(1950); with 11.R. Mtiller, JChemPhys with reducing materials. They are dangerous
19, 1319-20(1951) & CA 46, 4309(1952) 4) when heated to decompn, emitring highly tvxic
Partington(1950), 319 5)W.F.Claussen, JChemPhys fumes of bromine
19, 1425-6(1951) & CA 46, 4309(1952) 6)J. R~fs: 1 )B.Lewis & H. J. Schumacher, ZAnorgChem
Zernike et al, Rec 70, 784-92(1951) & CA 46, 182, 182-6(1929) &CA 23, 5426(1929) 2)H.J.
8500(1952) 7)H.R.Miiller & M.v.Stackelberg, Schumacher & R.V.T,ownend, ZPhysChem(Leipzig)
Naturwissenschaften 39, 20-1(1952) & CA 46, 20B, 375(1933) & CA 27, 2881(1933) 3) Partington
10998(1952) 8)Sax(1957), 383 (1950), 323 4)A.pflugmacher et al, ZAnorgChem
264$ 204-8(1951) & CA 47, 6752-3(1953) 5)A.
Bromine Oxides. The following compds are Pflugmacher, ZAnorgChem 273, 41-7(1953)&
described in the literature: B?omine monoxide, CA 48, 489(1954) 6)A.Pf lugmacher et al,
Br20, mw 175.83; dk-brn trysts, mp -17 ro -18° ZAnorgChem 279, 313-20(1955)& CA 49, 14550
(dec); can be prepd by the method of Schumacher (1955) 7)Sax(1957), 383-4

_ .—_—
—_...__ . ..----. =—-..--.— .- ....-..—.—._—_ .——.——
 B 307

Bromine Trioxide. See under Bromine Oxides isomers are ‘described in the literature:
2-Bromoanilir.?e, cryscs, mp 32°(Ref 1);
Bromoacetotie(BA) (called Brompropanon or 3-Bromoaniline, trysts, mp 16.8 °(Ref 2);
Bromaceton in Ger), CH2BKCOCH3 t mw 136.99, 4-Bromoaniline, malls, mp 66°(Ref 3). All of
col Iiq(when pure) with pungent odor, mp -54°, these isomers form numerous salts & addn
bp 136°, d 1.631 at OO; readily SO1 in alc* compds$ some of which are unstable and even
acet?eth and other org SOIVS; diffc sol in W; its explosive when heated. Other props and
prepn and other props are given in Beil(Ref 1). methods of prepn are given in the Refs
According to Sax(Ref 3), this compd is probably Re/s: l)Beil 12, 631, (313) & [341] 2)i3eil 12,
toxic but its toxicity details are not known 633, (315) & [342] 3)Beil 12, 636, (317) &
Wachtel(Ref 2) lists bromoacetone as first [3441
used in July 1915 in a war gas) called Ma~tonite Mononitrobromoani line, (0.#3r.C6H3.NH2; mw
(BA 80 + chloroacetme 20%) in Fr, B-StO// in 217.91 %. Seven isomers are described in the
Ger and BA in USA. This compd is a powerful literature: 4-Nitro-2-bromo-aniline, yel ndls,
Iachrymator. In sprays, it causes, in contact mp 104.5; 4-Nitro-3- bromoaniline, crysts(from
with the skin, painful blisters$ which heal within ale), mp 175-6°; 2-Nitro-4-bromo aniline, orn-yel
a short time. A concn of 1.5 mg/m3 causes tears ndls(from boiling w), mp 11 1.5°; 3-Nitro-4
immediately, 2.8 mg/m2 causes fighting -bromoaniline, flat ndls (from ale), mp 131°;
inefficiency, 560 mg/m3 is toxic and 3200 mg/m3 2-Nitro-j-bromo arziIine, red-yel ndls, mp 151 -2°;
is a lethal concn after 10 min exposure. Protection 2-Nitro-6-bromoaniline, yel ndls(from dil ale),
against the lachrymatory effect is possible by mp 73-5°; and 3-Nitro-6-bromoani2ine, yel ndIs
well-fitted goggles. Detection of BA in the (from ale), mp 141°. Some of these isomers
field is easily made by odor & irritation caused form salts & addn compds, some of which are
by the vapor(Ref 2) volatile and unstable.
Re/s: l)Beil 1, 657, (345) & [719] 2)Wachtel Other props & methods of prepn are given in the
(1941), 142 & 172-4 3)SaX(1957)> 384 Re/: Beil 12,737,738,739,(358) & [401,402,403]
Dinitrobromoaniline, (02N)2Br.C6}12.NHz; mw
f3romoacetyiene( Bromoethyne), CH~CBr; mw 262.03, N 16.04%. Eight isomers are described
104.9, gas, with an unpleasant odor, bp -2°, in the literature: 2, 3-Dinitro-4-bromoaniline,
vapor d 4.684; S1 sol in w or dil HN03; can be trysts, mp 158°; 2, 3-Dinitm-6-bromoaniline,
prepd by methods given in Beil(Ref 1). The dk-red crysts(from ale), mp 158°; 2, 4-Dinitro-5
toxicity details of this gas are unknown(Ref 4). -bromoaniline, k yld ndls mp 178°; 2, 4-Dinitro-6
It ignites and expl on contact with air or O but -bromoaniline, yel ndls(from AcOII or ale), mp
ignition can be inhibited by the addn of CS2, 153-4°; 2, 5-Dinitro-4-bromoaniline, yel trysts
C2H4 or S02(Ref 3) (from ale), mp 186°; 2, 6-Dinitro-4-bromo aniline,
Bromoacetylene forms some expl salts, orn ndls(from ale), mp 160-3°; 3, 4- Dinitro-6
such as Mercuri-monobromo acetylenide, -bromoaniline, It-yel crysts(from ale), mp 186°;
Hg(C:CBr)2, wh plates (from chlf), expl mildly and 3,,5 -Dinitro-2-bromoaniline, golden-yel Ifts
at 153-5°$ expl on rubbing against clay; was (from ale), mp 180-10. Other props & methods
prepd by Hofmann & Kirmreuther(Ref 2) are given in the Ref. These compds are weak
Re/s: l)Beil 1, 245 & (106) 2) K. Hofmann & H. explosives. Compare with props of Dinitroanilines ,
Kirmreuther, Ber 42, 4235( 19C19) 3)H0J0Emel:us VOl l,p A408-L
& H.V.A.Briscoe, JCS 1938, 1358-64 & CA 33, Re/: Beil 12,760,761,762,(367) & [417,418]
531(1939) 4)Sax(1957), 385 Trinitrobrornoaniline, (02N)3BtC6H.NH2; not
found in Beil or in CA thru 1956
Bromoaminomethy lbenzene. See Bromomethyl- Tetranitrobromoaniline, (02 N)4BrC6 .NH2; not
aniline found in Beil or in CA thru 1956

Bromoaminotoluene. See under Bromomethyl- Bromoazide. See Bromine Azide under Azides,
aniline and Derivatives Vol l,P A525-R

Bromoani line and Derivatives Bromoazobenzene and

Bromoanil ine(called Bromanilin in Ger), Derivatives
Br.C6H4.NH2; mw 172.04, N 8.15%. Three Bromoazobenzene( called Bromazobenzol in Ger),

\
 B 308

3rC=IIa.N:N.C6H5; mw 261.13, N 10.7%. Three Beil: 4’-Nitro-4-bromoazo.~ ybenzene occurs as

Isomers are described in the literature: 2- Brornoaz~ a- or low-melting form, crysts(from ale), mp
benzerre, mp 87°(Ref 1): 3- Brornoazobenzene, 194° and /3- or high-melting form, It-yel prisms
yel-brn lfts(from petr eth), mp 69°, volatilizes (from alc)$ mp 203 °(Ref 1); 2-Nitro-4-bromo-
w/o decompn; sol in ale, eth$ petr eth, chlf or azoxybenzerze, yel ndls(from petr eth), mp 99°
benz(Ref 2) and 4-Bromoazobenzene, orn-red (Ref 2); and 4-Nitro-2-bromoazo.vybenzene, yel
pltlts, ref flakes(from ale) or orn colored lfts crysts(from ale), mp 127° or yel ndls(from benz),
(from dil AcOH, mp 88-9° (Ref 3). Methods of mp 135-7°(Ref 3). Methods of prepn & other
prepn & other props are given in the Refs. Sax props are given in the Refs
(Ref 4) states that the toxicity of the para-isomer Refs: l)Beil 16, (378) & [317] 2)Beil 16,
is unknown but it is used as an insecticide (378) 3)Beil 16, (379)& [318]
Refs: l)Beil 16, 40 & [41] 2)Beil 16, 41 Ginitrobromoazoxxbenzene, C , *H7(N20)Br(N02)2;
3)Beil 16, 42, (223) & [14] 4)Sax(1957), 385 mw 367.13> N 15.3%. Only one isomer is listed
Mononitrolxornoazobe nzene, C, ~H8N2Br(NO~; in Beil: 2, 6- Dinitro-4-bromo azo.xybenzene, lt-yel
mw 306.12, N 13.77.. Four isomers are listed ndls~from AcOH)} mp 163°; prepn & other props
in Beil: .wNitro-3-bromoazo benzens, orn-red are given in the Ref
ndls, mp 123°;. r-Nitro-4-bromoazob enzene, yel Re/: Beil 16, (379)
ndls~ mp 107-8°; 2-Nitro-4’ -bromoazobenzene, Trinitrobromoazoxy benzene, C , ~HG(N20)Br(N02)3;
brick-red lfts with a golden-grn shimmer, mp mw 412.13, N 17.070. Onl~ one isomer is described
152.5°; and 4- Nitro-4’-bromoa zobenzene, in the literature: 2,6,3’ (?)- trinitro-4-bromo azo.vy-
dk-red crysts(from benz), mp 203°. Methods of benzene, yel-grn crysts(from benz), mp 209°(dec);
prepn & other props are given in Beil diffc sol in ale; was prepd by heating 4-bromo-2
Ref: 13eil 16,41,42,51,(226) & [17] -nitroazoxybenzene with HN03(d 1.52) on a w
Dinitrobromoazobenzene$ C ~F!7Nz Br(N02)2; bath(Refs 1 & 2)
mw 351.13, N 16.o%. Two \ somers are Ilsted Re/s: l)Beil 16, (379) 2)B.Valori, AttiAccad-
in Beil: .x, x-D initro-4-brorno azobenzene, ndls~ LinceiRend [5] 22 II, 133(1913) & JCS 104 I>
mp 190° and 2, 4-Dinitro-4’ -bromoazobenzene, 1110(1913)
red ndls, mp 175°. Other props & methods of Note: Higher nitro derivs of bromoazoxybenzene
prepn are given in the Ref were not found in Beil or in CA thru 1956
Ref: Beil 16, 42 & 58
Trinitrobromoazobenzene, Cl ~E16N2Br(N02)3; Bromobenzazimidol. See Bromobenzohydroxy -
mw 396.13, N 17.7%. Only one isomer is triazole
described in the literature: 2,4, 6- Trinitro-4’
-brornoazobenzene, red ndls(from ale), mp 170.5°; Bromobenzene and Derivatives
was prepd either by bromination of 2,4,6-trinitro Bromobenzene or Pbenyl Bromide(called
-hydrazobenzene or oxidn of 4’-bromo-2 ,4,6 Brombenzol in Ger), C6H .Br; mw 157.02, clear,
-trinitrohydrazobenzene with chromic acid & colt mobiIe Iiq, fr p -30.73, bp 156.2°, flash p
AcOH(Refs 1 & 2). Its expl props were not detd 149 °F(closed cup), d 1.497, vap press 10mm at
l?e~s: 1 )Beil 16, 59 2)C.Willgerodt & L.Elton, 40°, vap d 5.41; prepn & other props are given
JPrChem 44$ 71(1891)& JCS 6011. 1361-2(1891) in 13eil(Ref 1). Sax(Ref 2) lists this compd as mod
Note: Higher nitro derivs of b romoazobenzene toxic & mod dangerous when exposed to heat or
were not found in Beil or in CA thru 1956 flame
Refs: l)Beil 5, 206, (113) & [ 158] 2)Sax(1957),
Ehomoazoxybenzene and Derivatives 385
B romoazoxyhenzene( called Bromazoxybenzol in Azidobromobenzene, C6H4.Br(N~ mw 198.03,
Ger), BrC6H4(N20)C6H5; 277.13, N 10.1%. Two N 21 .22%. The following compds are described in
forms of the 4-Bromoazo.vybenzene are described the literature: l-Azido-2-bromobenzene, vol with
in the literature: the a or low-melting form; steam; l-Azr’do-3-brornobenz ene, bp 99° at 10mm;
straw-yel ndls(from ale), mp 73° and ~ or high and l-Azido-4-bromobenzene, lfts, mp 20°, bp
-melting form, yel crysts(from petr eth), mp 93°. 105° at 10mm. Ptepn & other props of these
Prepn & other props are given in Beil azido derivs are given in the Ref
Re/: Beil 16, (377) & [315] Re~.’ Beil 5, 277, (142) & [208]
Manonitrobrornoazoxy benzene, Cl* H~(N20)Br.N02; Azi donitrobromoben zeme, 02N.C6H3.Br[N$ mw
mw 322.12, N 13.0%. Three isomers are listed in 243.03, N 23.06%. Three isomers are described

—— 1 ,.— .-_... ”_..

 B 309

in the literature: 1-Azido-2-nitro- 4- bromobenzene, & in stable form as ndls(from ale) or pltls(from
almost CO1 ndls(from benz + pert eth), mp 80°:, alc + eth), mp 59.5 °(Ref); and 1,3-Dinitro-4
readily sol in benz or acet$ sol in MeOH or ethyl -bromobenzene, yel crysts(from ale), mp 75.3°
ale, v S1 SOI in petr eth(Refs 1 & 2); l-Azido-2 [Ref,p 266 & (138)]. The .Prepn & other proPs
-nitro-5-bro moberzzene, yel pltls or prism s(from of these derivs are given in the Ref
petr eth), mp 66°, readily SOI in benz,. acet or eth Ref.’ Be.il 5, 266, (138-9) & [201]
acet(Refs 1 & 2): and 1 -Azido-3-rzitro-6 -bromo- 4=Nitroso-1 ,3-Dinitro=5-bromobenzene,
benzene, straw-yel ndls(from ale), mp 58°(Ref 3). (02 N)2C6H2(NO)Br; mw 276.02, N 15.22%; dk-yel
All derivs were prepd by diazotizing the crysts(from AcOII), mp ca 99° giving a grn liq;
appropriate bromonitroaniline with NaN02 and sol in AcOH giving a dk grn color; was prepd by
adding NaN3. All of these derivs yield, on oxidg ~-(6-bromo-2,4-dinitrophenyl)-hydroxylamine
heating to 110°, bromobenzofuroxan( Refs I, 2 & 3) with chromic acid. Its expl props were not detd
Re/s: l)Beil 5, (143) 2)M.0.Forster & M.F. Ref: Beil 5, [203]
Barker, JCS 103 II, 1920-1(1913) 3)G.Tappi & Trinitrobromoben zene, (02N)3 C6H2 .Br; mw
P. V. Forni, AnnChimApplicata 39, 338-43( 1949) & 292.02, N 14.39%. Three isomers are described
CA 46, 2540(1952) in the literature: 1,2,4- Trinitro-j-bromobenzeae,
Diazido bromobenzene, C6H3BE(N~ )2, and ndls(from alc)$ mp 120-1°; readily sol in ale, eth,
Triazido bromobenzene, C6H2Br(N3 )3, not found benz, acet or chlf; SI sol in petr eth; was obtd as
in Beil or in CA thru 1956 the chief product from the nitration of 1,2-dinitro
Nitrosobromobenzene, 0N.C6H4.Br; mw 186,02, -4 -bromobenzene(Refs 1 & 3); I, 2, 4- Trinitro
N 7.53%. Three isomers exist and are described -6-bromobenzene, yel crysts(from alc or AcOH),
in the literature: 1 -Nitroso-2-bromo benzene, mp 10 1°; was prepd by nitrating 6-bromo-2,4
CO1 ndls$ mp 97.5-98°; l-Nitroso-3-bromobenzene, -dinitropheylhydroxy lamine with 2ps HN03(Refs
trysts, mp 78°; and 1- Nitroso-4- bromobenzene, 1 & 5); and 1, 3,5- Trinitro-2-bromobenzene or
CO1 ndls(from ale), mp 95°. Other props & Picryl Bromide, yel.wh pltls(from ale), mp
methods of prepn are given in BeiI 122-3°; was pre pd by nitrating 1,3-dinitro-4
Re/: Beil 5, 232, (124) & [171] -bromobenzene(Refs 2 & 4). These isomers are
Mononitrobromobenzene, 02N.C6H4 .Br; mw all expl compds although their expl props were
202.02, N 6.94%. Three isomers are described not reported
in the literature: l-Nitro-2-bromobenzene, lt yel Refs: l)Beil 5, [206-207] 2)Beil 5, 275 &
slender ndls~ mp 38-45°; l-Nitm-3-brOmObenzene, [ 207] 3)M.Giua, G azz 51 I, 309(1921)& JCS
exists in unstable form, mp 17.5° & in stable 120 I, 551(1921) 4)A.H.Rheinlander, JCS 12311,
form as rhomb prisms, mp 54-6°; and l-Nitro-4 3110(1923) 5)W ,Borsche & E. Feske, Ber 59,
-brornobenzene, triclinic prisms, mp 125-7°, 685( 1926) & CA 20, 2666(1926)
explodes on heating to 755°. The prepn & other Note: Higher nitro derivs of bromobenzene were
props are given in the Ref not found in Beil or in CA thru 1956
Re/: 13eil 5, 247-8, (131-2) k [188]
1.Nitroso-4.nitro.2-bromobenzene, 02 N. C6H3(N0)- Bromobenzohydroxy triazole
.Br; mw 231.02, N 12.13%; It yel crysts(from ale), and Derivatives
mp 123°, giving a grn liq; was prepd by treating Bromobenzohydroxytriazole or Bromo~enzazimidol,
2 ,4-nitrobromoaniline with aq K2S04 soln & coned Br.C6H4N30; mw 214.03, N 19.64%. Two
H2S04 and distilling the filtrate. Its expl props isomers are described in the literature: 5-Bromo-
were not detd benzo- l-hydroxy-a-vic- triazole [ called l-Bromo-
Re/s: l) Beil-not found 2)D.Bigiavi et al, Gazz ben,zo-3,4(3‘-azimidole) by Mangini(Ref 2)],
61, 392-6(1931) & CA 26, 120(1932) H;-CHZ C-N(OH)
Dinitrobromobenzene, (02N)2CGH3.Br; mw 247.02, j NN ~ hex prisms(from ale), mp
N 11 .34%. The following isomers are described Bx C-CHCC-N’
201. 5-2. flexpl decompn); was prepd by boiIing
in the literature: 1, 3-Dinitro-2-bromobenzene, yel
an alc suspension of 2,5-02 N(Br)C6H3NH.NH2
prisms(from ale), mp 107° [Ref ~P(138)] ; 1,4
with 5yo alc KOH and acidifying the reaction
-Dinitro-2-brornobenzene, ndls (from ale) or prisms
mixt(Ref 2); and 6- Bromobenzo-l -bydroxy-a-vic
(from ale+ eth), mp 70° [Ref,p(139)] ; 1,2
-triazole [ called l-Bromobenzo-3 ,4-( 1‘-azimidole)
-Dinitro-3-bromobenzene, yel pltls(from ale), mp
by Mangini(Ref 2) and l-Oxy-6-brom-benztriazol
101.50 [Ref,p 266 & (138)]; 1,2-Dinitro-4
or 6-Brom-ben zazimidol in Ger(Ref 1)],
- bromobenzene, exists in unstable form, mp 34.8°
 B 310

Br.C-CH.C-N(OH) prepd by adding NaN02 soln to rhe HC1 of 6-bromo

H! . ~11=:-“ >
? ‘ : col prism s(alc + HC1), mp -4-nitro-2-aminophenol( Refs 1 & 2); 2-Diazo-6
-nitro-4-bromo-l, 2- benzoquinone [called 4-Brom-6
188-96 °(decompn); w?sprepd by heating 2,5 -nitro-2-diazo-phe nol or 5- Brom-3-nitro-o-chinon
-dibromo-l-nitrobenzene with an excess of
-diazid-(1) in Ger] , brn ndls having greenish
hydrazinehydrate in, dilalc(Refs 1,2 &3)
metallic luster, mp explodes with extreme violence
Re/s: l)Bei126, [26] 2)A.Mangini, Gazz 66,
at ca 144°; was prepd by ad ding NaNOz sohr to
675-84( 1936) &CA 31, 4961(1937) 3)S.S.Joshi&
the HC1 of 4-bromo-6-nitro-2 -aminophenol(Refs I &
D.S.Deorha, JIndianChemSoc 29, 545-8( 1952) & CA
3); and 4-Diazo-2-nitro-.5 -bromo- 1,4- benzoquinone
47, 8738-9(1953)
(called 5-Brom-2-nitro-l ,4-quinone azide in CA),
Mononitrobromobenzohydroxytriazole or
yel-brn trysts, mp 186 °(dec & explodes); was prepd
Mononitrobromobenzazimidol, Br.C6H3(N02)N30 ;
by bromination of 2,3, 5-trinitro-4-amino-ph eno@ef
mw 259.03, N 21.63%. Two isomers are described
4)
in the literature: 4- Bromo-6-nitro-l -bydroxy-a-vic
Re/s: l)Beil 16, 524 2)R.Meldola et al, JCS 69
-triazole, k orn-brn trysts, mp 205°; and 6-Bromo
II, 1327(1896) 3)R.Meldola & F. H. Streatfield, JCS
-4-nitro-l-bydroxy-a-vic-ttiazole, yel trysts, mp
73, 688(1898) 4)G.Heller et al, JPraktChem 129,
208°. These and other substituted derivs of
217 & 241(1931); CA 25, 2129(1931) & BrA
benzazimidole were prepd from chloronitrobenzene
1931A, 478
and hydrazine or substituted hydrazine(Ref 2)
2-Bromo-1,4-benzoquinone-l-oxime [called 2-Brom
Re/s: l) Beil-not found 2)S.S.J oshi & D.S. -p-chinon-oxim-(1) in Ger] , 0: C6H3(Br):N.0H;
Deorha, JIndiaqChemSoc 29, 545-8(1952) & CA mw 202.02, N 6.97.; pale greenish crysts(from
47, 8738(1953) benz), mp 190-6°; other props & methods of prepn
Note: IIigher bromonitro derivs were not found in are given in the Ref
Beil or in CA thru 1956. See chloro, dichloro & Re/: Beil 7, [583]
other derivs under Benzotriazolol and Derivatives,
2-Bromo-l,4-benzoquinone-4-oxime [called 2-Brom
p B88 -p-chinon-oxim-(4) or 2-Brom-4-nitroso-phenol in
Ger] , 0: C6H3(Br):N.0H or H0.CGH3(Br).N0,
Bromobenzoquinone and
See 4-Nitroso-2-bromophenol under Bromophenol
Derivatives
and Derivatives
Bromobenzoquinone( called Brom- benzochinon or
2-Bromo-1,4.benzoquinone.4.methylimine.l.oxime
Bromchinon in Ger), 0: C6H3(Br) :0; mw 187.00.
[called 2-Brom-p-chinon-methylimid-(4)-oxim-(1) or
Only the 2- Bromo- 1, 4-benzoquinone is known,
3-Brom-4-nitroso-methy lanilin in Ger] ,
orn-Yel crYsts(frorn petr eth), mp 56.5°, sublimes
H3C.N:C6H3(Br): N.0H or H3C.HN.CeH3(Br) .N0.
when carefully heated; other props & methods of
See 4-Nirroso-3-bromonethy laniline under
prepn are given in the Refs
Bromomethylaniline and Derivatives or 3-Bromo
Refs: l)Beil 7, 639 & [583] 2)A.N.Grinev & A.P.
-1,4 -benzoquinone-l-methy limine-4-oxime under
Terenr’ev, ZhObshchKhim 25, 2145-6(1955) & CA
Benzoquinone Oxime and Derivatives
50, 8509( 1956) 3)p .Souchay et al, J WsRadium
15, 533-5(1954) & CA 50, 9879( 1956)(IR absorption
Bromobenzoyl Azide
spectrum)
and Derivatives
2-Diazo-3-bromo-o-benzoquinone [called 3-Brom
Bromobenzoyl Azide(called Brom-benzazid in
-2-diazo-phenol or 3-Brom-o-chinon-diazid-(2) in
Ger), Br.C6H4.C0.N3; mw 226.03, N 18.59%.
Ger] , 0: C6H3(Br):N2; mw 199.02, N 14.08%;
Three isomers are described in the literature:
orn CO1 prisms(from eth), mp 103 °(dec), v
2-Bromobenzoyl Azide. Prepn & props given in
sensitive to light; was prepd by treating 2,6-di-
Ref 3, which was not available for review;
bromobenzenediazonium sulfate with aq Na
3-Bromobenzoyl Azide, COI oil having disagreeable
acetate soln for 4 days(Refs 1 & 2)
odor and producing tears; mp expl violently on
Re/s: l)Beil 16, 523 2)K.J.P.Orton, JCS 83,
heating; readily sol in ale, eth, acet or chlf; insol
812(1903)
in w; was prepd by the action of nitrous acid on
Mononitrodiazobromobenzoquinone, 0:CGH2(N02)-
3-bromobenzhydrazide( Refs l,p 351 & 2,p 195)
(Br):N2; mw 244.02, N 17.22%. Three Isomers
4-Bromobenzoyl Azide, CO1 plates(from acet),
are described in the literature: 2-Diuzo-4-nitro-6
mp 46°, expl at higher temps; readily sol in alc,
-bromo-1, 2-berzzoquinone [ called 6-Brom-4-nitro
acet or eth; insol in w; was prepd by the action of
-2-diazo-phenol or 6-Brom-4-nitro-o-chinon-diazid
nitrous acid on 4-bromobenzhydrazide(Refs l,p
(2) in Ger] , yel ndls(from w), dec ca 152-3°; was
 B311

355 & 29P 201) the lungs and can produce acute congestion &
I?e/s: l)Beil 9, 351 & 355 2)T.Curtius & E. endema. It is much less toxic than methyl bromide,
Portner, JPraktChem 58, 195 & 201(1898) & JCS but more toxic than ethyl chloride
76 I, 136(1899) 3)P.P.T.Sah et al, JChineseChem- Refs.’ l)Beil 1, 88, (26), & [59] 2)Sax(1957),
SOC 13$ 22-76(1946) & CA 42, 148(1948 )(Describes 668
the use of these compds as reagents for identific- 1-Azido-2-bromoethane, N3.CH2.CHz.Br; mw
ation of alcohols, amines & phenols) 149.99, N 28.02%; COI Iiq, having an odor of
Mononitrobromobenzoyl Azide, Br.C6H3(N02).C0.- ethylene dibromide & rapidly becoming yel when
N3; not found in Beil or in CA thru 1956 exposed to light, bp 49° at 20mm, d 1.6675 at
Dinitrobromobenzoyl Azide, Br.CGH2(NOz)2.C0.- 19°; does not ignite when thrown on a hot plate
N3; mw 316.05, N 22.16%. Two isomers are but merely crackles; was prep.d from @-azido-
described in the literature: ~, 5-Dinitro-2 ethanol by the action of PBr3(phosphorus
- bromobenzoyl Azide, yel trysts, mp 67°(dec); tribromide) in petr eth(Refs 1 & 2)
was prepd by conversion of the corresponding Re/s: l)BeiI 1, (33) 2)M.O.Forster & S.H.
chloride in glac and AcOH by reaction with Na Newman, JCS 9711, 2571-7(1910)
azide(Ref l,p 997) and 1-Nitro-1-bromoethane,< 02 N. BrCH.CH3; mw
3, 5- Dinitro-4-brornob enzoyl Azide, COI fine ndls 153.97, N 9.09%; vol liq boiling at 146-7° w/o
(from petr erh), mp 116°; was prepd by addn of decdmpn; insol on w; prepn & other props are
Na azide to 4-bromo-3, 5-dinitrobenzoyl chloride given in Beil
suspended in glac AcOH. Although its expl props Re/: l)Beil 1, 101 & (32)
were not investigated this compd is an expl. 1,1-Dinitro-l-bromoethane, (02 N)2Br.C.CH3; mw
Compare with the props of 3,5-dinitrobenzoyl 198.98, N 14.62%; oily Iiq, VOI with steam; dec
azide under Benzoyl Azide and Derivatives (Ref on heating$ with bromine splitting off; somewhat
2,p 991) sol in w; prepn & other props are given in Beil.
Re/s: l)Beil-not found 2)J .J.Blanksma & G. Its expl props were not reported
Verberg, Rec 53, 991 & 997(1934) & CA 29, 462 Re/: Beil 1, 102 & [70]
(1935) Note.’ Higher nitro derivs of bromoethane were
Trinitrobromobenzoyl Azide, Br.CGH(N02)3.C0.- not found in Beil or in CA thru 1956
N9; not found in Beil or in CA thru 1956
Bromoethanol and
Bromobenzoyl Azidodithiocarbonate. See Vol Derivatives
1,p A633-L under Azidodithiocarbonic Acid and 2-Bromoethanol [called 2-Bromhthano~-(1), ~-Brom
Derivatives -hthylalkohol, ~thylenbromhydrin or
Glykolbromhydrin in Ger] , Br.CHz .CH2.0H; mw
N-(4-Broma-2,4-dinitrophenyl)-N-nitro-ß-aminoethyl 124.98; COI hygr liq, dec on distilling at atm
Nitrate, See 2,4-Dinitro-4-bromopheny lnitramino- press, bp ca 148° with partial decompn, bp 56-7°
ethyl Nitrate to be described under Phenyl- at 20mm$ d 1.7494 at 30°; other props & methods
aminoethanol and Derivatives of prepn are given in Ref
Re/: Beil 1, 338, (170)& [337]
N-(5-Bromo-2,4-dinitrophenyl)-N-nitro-ß-aminoethyl 2-Bromoethylnitrate, Br.CH2.CH2.0N02; mw
Nitrate. See 2 ,4-Dinitro-5-bromopheny lnitramino- 169.98, N 8.2%; oily Iiq, bp beginning ar 132°
ethyl Nitrate to be described under Phenylamino- with a portion at 163-50, d 1.78; was prepd from
ethanol and Derivatives ethylene, bromine & NaN03 soln. Before
distillation the oil was washed with NaHCO~ to
Bromoethane and remove any trace of HN03. In the distillation the
Derivatives Iast trace exploded with the evolution of bm
Bromoethane, Ethyl Bromide, Bromic Ether or nitrous fumes(Refs 1 & 2)
Hydrobromic Ether(called Brom~than or Re/s: l)Beil 1, 339 & [338] 2)A.W.Francis,
~thylbromid in Ger), CH3.CH2.Br; mw 108.98; JACS 47, 2347(1925)
CO1 vol liq, fr p -119°, bp 38.4°, d 1.430 at 20°; 2-Nitro-2-bromoethylnitrate, Br.CH(N02).CH2.-
vap press 400mm at 2 1‘C; prepn & other proPs are ON02; mw 215.02, N 13.05%; viscous yel liq,
given in Beil(Ref 1). Sax(Ref 2) lists this compd d 2.438 at 1lO; was prepd by treating 2-bromo-2
as an anesthetic & narcotic. It readily dec into -nitroethanol with a mixt of nitric & sulfuric acids
vol toxic products which are markedly irritating to (Refs 1 & 2). The chloro deriv detonates on
 B 312

rapid heating; Ref l,P [340] Re/s: l)Beil 1, 77, (21) & [43] 2)Vivas,
Refs: l)Beil 1, 340 & [340] 2) J.h4aas, Rec 17, Feigenspan & Ladreda, VOl 2(1946), 21 3)p.
389(1898) & JCS 761, 322(1899) Fischer, JPharmBelg [NS] 2, 225-9(1947) & CA
2-Nitro-2-bromoethanol, Br.CH(N02).CH2.0H; 42, 699(1948) 4)J .D.B.Ogilvie et al, CanJRes
mw 169.98} N 8.2%; thick yel liq having a pungent 26F, 246-63(1948) & CA 42, 7967(1948) 5)Sax
odor$ bp 147-8° at 45mm, d 2.084 at 10°; sol in (1957), 387
alc or eth; S1 sol in w; was prepd by fhe
condensation of bromonitromethane with formalde- Bromoformamidine Nitrate. See under Formamidine
hyde in the presence of K carbonate and by other and Derivatives
methods(Refs 1 & 2)
Its K(Ref 4) & Na(Ref 3) salts were prepd, Bromoformamidine Perchlorate. See under
the corresponding chloro derivs of which expl on Formamidine and Derivatives
heating in a flame
Re/s: l)Beil 1, 339 & [340] 2) J. Maas, Rec 17, Bromomethane and Derivatives
3%(1898) & JCS 76 1,322(1899) 3)R.Wilkendorf Bromomethane or Methylbromide(called Brommethan
& M. Tr~nel, Ber 56, 611(1923) & CA 17, 2414-5 or Methylbromid in Ger), CH3 .Br; mw 94.95; CO1
(1923) 4)M.Tr~nel & R.Wilkendorf, Ber 57, 2126 transparent vol gas or Iiq, fr p -93°, bp 3.56°,
(1924) & CA 19, 1406(1925) autoig”n temp 998°F, vap d 3.27; other props &
Note: Higher nitro derivs of bromoethanol were methods of prepn are given in Beil(Ref 1)
not found in Beil or in CA thru 1956 According to Sax(Ref 2), bromomethane is 8
times more toxic on inhalation than bromoethane.
Bromoform and Derivatives Its MAC(max allowable concn) is 20ppm in air or
Bromoform or Tribromamethane( called Bromoform, 78mg/m3. Death following acute poisoning by
Methenylbromid or Tribrommethan in Ger), CHBr~; bromomethane is usually caused by its irritant
mw 252.77, CO1 liq or hex trysts, mp 6-7°, bp effect on the lungs. In chronic poisoning, death
149.5°, d 2.890 at 20°. Other props & its method is due to injury to the central nervous system.
of prepn are given in Beil(Ref 1) Fatal poisoning has always resulted from
According to Sax(Ref 2), bromoform has exposure to relatively high concns of vapors
anesthetic props similar to those of chloroform (8600 to 60000 ppm). LocalIyt bromomethane is an
but it is too toxic to be recommended for this extreme irritant to the skin and may produce
purpose. The inhalation of small amts causes severe burns
irritation flow of tears & reddening of the face. Refs: l)Beil 1, 66, (15) & [31] 2)Sax(1957),
[n addn to its narcotic effects, it is a metabolic 883-4
poison. It can damage the liver to a serious Mononitrobromomethane, CH2Br.N02; mw 139.96,
degree & cause death N 10.01%; corrosive Iiq having a penetrating odor,
Re/s: l)Beil 1, 68, (16) & [33] 2)Sax(1957), fr p -28°, bp 152.5° at 765mm press; other props &
387-8 methods of prepn are given in i3eil
Nitrobromoform, Bromopicrin or Tribromonitro- Ref.’ Beil 1, 77, (21) & [43]
methone, 02 N, C.Br3; mw 297.78, N 4.71%; Dinitrobromomethane, CHBr(N02)2; mw 184.96,
prismatic trysts having a strong odor, mp ca N 15.15%. Its K saIt, K..C. Br(N02)2, wiclinic yel
10.3°, bp 127° at l18mm & 85° at 17mm; expl on crysts(from w), expl on heating to ca 145°; in aq
heating at atm pressure evolving a red-brn vapor; soln with AgN03 yields the Ag salt, Ag.C. Br-
d 2,781 at 20°; other props & methods of prepn (N02)2, yel expl ndls which become steeI-blue in
are given in Beil(Ref 1) air. Other props & methods of prepn are given in
Ogilivie et al(Ref 4) found that bromopicrin, the Refs
choloropicrin} Br & other compds caused an
Refs: l)Beil 1, 78, (21) & [44] 2)M.Tr~nel & R.
increase in the knocking tendency in aviation Wilkendorf, Ber 57B, 2126(1924) & CA 19, 1406
gasoline. These compds counteracted the effect
(1925)
of antiknock additives & also had some effect on Trinitrabromomethane, Br.C(NOz)3; mw 229.95,
the base stock fuel
N 18.27%; clear liq with a faint grn-yel tinge,
A method for determining the quantity of fr p 10-18°, bp 59° at 8mm & 68° at 20mm, at atm
bromopicrin & certain other poisons or vesicants press decompn takes place, d 2.07 at 19°, n~
by reaction with sulfhydryl(-SH) substances was 1.4900 at 19°; Raman & IR spectra have been
reported by Fischer(Ref 3) reported by Mathieu & Massignon(Ref 3); was
 B 313

prepd by the action of Br or HBr on nitroform 1261, 1120(1924)

(trinitromethane) in HNOa soln or K nitroform & Mononitrobromomethylaniline, C7H7N20zBr; mw
Br in eth and by other methods(Refs 1 & 2). Its 231.07, N 12.12%. The Mononitrobromo-N
expl props were not reported -metbylarziline isomers, 02 N.C6H3 Br.NH.CHa, are
Re/s: l)Beil 1, 79, (21) & [46] 2)A.K.Macbeth described in Ref 1 and the Mononitrobromo-
& D,D.Pratt, JCS 119 I, 356(1921) & 119 II, 1357 aminotoluene isomers, 0zN.CGH2(Br)NH2 .CH3,
(1921) 3)J.P.Mathieu & D.Massignon, AnnPhys are described in Ref 2. AH of the N-methyl-
16, 5(1941); ChemZtr 194211 24& CA 37, 4304 aniline isomers and all of the methylaniline
(1943) isomers are colored trysts compds. Their props &
methods of prepn are given in the Refs
Bromomethylaniline and Re/s: l)Beil 12, 737, 738,739 & [401,402]
Derivatives 2)Beil 12, 850,851,878,1007 ;(395,409,441) &
Bromomethylaniline, Bromoaminomethylbenzene, [462,479]
Brornoarninotoluerze or Bromotoluidine( called Mononitro.N.nitroso.bromethylaniline or
Brom-methylanilin or Brom-aminotoluol in Ger), Nitrobromophenyl.methylnitrosamine,
C7H~NBr; mw 186.06, N 7.53%. The Brorno-N 02N.C6H3Br.N(NO) .CH~; mw 260.06, N 16.16%.
-metbylarzizine, isomers, Br. C6H4.NH. CH3 * are Two isomers are described in the literature:
described in Ref 1 and the Bromo-aminotoiuene 2-Nitro-N-nitro so-4-b romo-N-metbylan iline or
isomers: Br.C,sHa NHz.CH3, are described in Ref (2-Nitro-4-bromop henyl)-metb ylnitrosamine,
2. Most of these compds are liquids or low crysts(from MeOfI), mp 73 °(Refs 1 & 2> and
-melting crpts. Many form salts & addn compds, 3-Nitro-N-nitroso- 4-bromo-N-metby laniline or
some of which are unstable. Other props & methods (3-N itro-4-bronopbeny l)-metbylnitrosoamine,
of prepn are given in the Refs yel ndls(from MeOH), mp 78 °(Refs 1 & 2).
Re/s: l)Beil 12, 637, (317) & [341,345] 2)Bei1 Other props & methods of prepn are given in
12, 837,838,839,873,991, (389,390; 436) & [455, the Refs
456,474,532] Re/s: I)BeiI 12, [401,402] 2) W.G.Macmillan &
Nitrosobromomethylaniline, C7H7N20Br; mw T.H.Reade, JCS 1929, 2866
215.07, N 13.03%. The following isomers are Dinitrobromomethylaniline, C7H6N304Br; mw
described in the literature: 4-Nitroso-2-brorno- 276.06 N 15.22%. Three N-methyl derivsd
metbylaniline or p- Quinone-l-metby Iimine-2 (02N)2C~H2Br.NH. CH3, are described in the
-bromo-4-oxime, (ON)Br.CGH3.NH,CH3 or literature: 2,4.Dinitro-5-bromo-N-methylaniline,
HON :C6H3(Br):N.CH3, blue-grn crysts(from benz), yel crysts(from ale), mp 149-1 50°; “2, 4- Dinitro-6
mp 87°(Refs 1 & 6) & 104 °(Refs 1 & 3); 4-Nit~so -bromo-N-metAylaniline, \ yel crysts(from AcOH),
-3-bromometbylaniline or p-Quinone-f-metby limine mp 147°; and 2, 6-Dinitro-4-bromo. N.methylaniline,
-3-bromo-4-oxime, grn trysts, mp turns dark at orn ndls or yel crysts(from alc or petr eth), mp
100° & expIodes at 124°; its Hydrocb[oride sait, 104-6°(Ref 1). Two aminotoluene or methylaniline
red, turns yeI at 140° & melts with decompn at derivs, (02N)2C=H(Br)NH2 .CH3, are described
168°(Refs 1 & 4); N- Nitroso-2-bromo- N-methyl- in the literature: 4,6-D initro-3-bromo-2-m ethyl-
aniline or (2- Bromo@benyl)-methy lnitrosamine, aniline, yel trysts, mp 200°; and 3, S-Dinitro-2
Br.C6H4 .N(NO).CH3, vol on steam bath(Refs 2 & -bromo-4-metbyIaniline, It yel ndls or prisms
6); N-Nitroso-3-bromo.N-methylaniline or (3 (from ale), mp 170-4°(Ref 2). Other props &
- Bromopbenyl)-metby lnitrosamine, yel ndls, mp methods of prepn are given in the Refs
43-4°(Refs 2 & 5) & 49°(Refs 2 & 4); and Re/s: l)BeiI 12, 761 & [417, 418] 2)Beil 12,
iV-Nitroso-4-bromo- N-metbylmiline or (4-Bromo - (397, 445) 82 [5401
phenyl)-rnetbylnitrosamine, COI ndls(from ale),
mp 2,6.Dinitro.N.nitroso.4.bromo.N.methylaniline or
74-8 °(Refs 2,3,5 & 6). Other props & methods of 2,6.Dinitro.4.bromophenyl).methylnitrosamine,
prepn are given in the Refs (02 N)2C~H2Br.N(NO). CHa; mw 305.06, N 17.14%;
Refs: l)Beil 7, (348) & [583,584] 2)Beil 12, lt-yel ndls(from ale), mp 124°; was prepd by
[342,343,354] 3)0.Fischer & P. Neber, Ber 4~* treating 4-bromodimethylaniline with mixed
1097, 1101(1912) & Jcs 102 I%438(1912) 4)Mos0 HNC)3-H2S04 below 400 or 2-nitro-4-bromo-
Kharasch & J .F.Piccard, JACS 42, 1858-9(1920) dimethylaniline with 52% HN03 betw 10-35°
5)E.Schmidt & R.Schumacher, Ber 54, 1415-6 (Refs 1 & 2). Its expl props were not detd
(1921) & JCS 1201, 660(1921) 6)E.Votocek & R. Re/s: l)Beil 12, [419] 2)G.R.Clemo & ].M.
Lukes, BullFr [4] 35, 874, 879(1924) & JCS Smith, JCS 1928, 2421
 B 314

Trinitrobromomethylaniline, C7H5N406Br; mw C02 -36,2%; pale yel ctysts(from acet + w), mp

321.06, N 17.45%. The following isomers are 118-9°(dec); was prepd by addg liq Br to an aq
described in the literature: N, 2,4-Ttin itro-6 KOH soln of N-methyl-ethylenedinitramine and
- bromo-N-m ethylaniline; 2, 4-Dinitro-N-nitro-6 stirring with subsequent cooling. The following
-bromo-N-metbyIaniline or (2,4-D initro-6 expl props were reported: Explosion Temperature,
-bromopbenyl)-metbylnitramine, (02N)2CGH2Br.- no expln at 360° in 5 sees; impact Sensitivity
N(N02).CH3, col trysts, mp 125°; was prepd by 6.6cm at 50% point(RDX= 35cm); Power by
nitration of either 4-nitro-2-bromo-N-methy laniline Ballistic Mortar Test, 101$Z TNT; Thermal
or 2,4-dinitro-6-bromo-N-methylaniline(Refs 1 & 3~ Stability by 135° Heat Test, sample ignited in
and N,2, 6-Tn”nitro-4-bromo-N-m etbylaniIine; 4mins
2, 6-Dinitro-N-nitro-4 -bromo-N-metbylaniline or The dry compd is more stable than dry
(2, 6-Dinitro-4-bromopbenyl)-metbylnitramine, dibromo deriv. The N halogen derivs of aliphatic
CO1 trysts, mp 110° or It yel ndls(from ale), mp nitramines were prepd and studied for possible
113-4°; was prepd by nitration of either 2-nitro-4 uses as tracer compds and in detonator compns.
-bromo-N-methylaniline or (2 ,6-dinitro-4-bromo- Attempts to prep the iodo derivs were unsuccessful
phenyl)-methylnitrossmine(Refs 2,3 & 4). These because they are too unstable to be isolated and
compds will defgr or expl when heated above purified
their rep’s, but their expl props were not detd R e/s: l)Beil & CA- not found 2)A.T.
Refs: l)Beil 12, 761 2)Beil 12, 762 & [419] Blomquist, “Certain Aliphatic Nitramines and
3)J.J.Blanksma, Rec 21, 271-2(1902) 4)G.R~ Related Compounds”, OSRD Rpt 4134( 1944),pp
Cleo & J.M.Smith, JCS 1928, 2421-2 12-15, 69-70 & 86(PB NO 18867)
Tetranitrobromomethylaniline, C7H4N50*Br; mw
366.06, N 19.13%. Tkee isomers are described in Bromonicotinic Acid
the literature: N,2,3, 4- Tetranitro-6-bromo-N and Derivatives
-rnetbylaniline; 2, 3,4-Trinitro-N-ni tro-6-bromo-N Bromonicotinic Acid or 5-Bromopyridine-3
-metbylaniline or (2,3,4 -Tn”nitro-6-bromopbenyl) -carboxylic Acid [called 5-B rom-pyridin
-metbylnit ramine, (02N)3 C6 HBr.N(N02).C~, - carbon s~ure-(3) or 5- Brom-nicotins2ure in Ger] ,
trysts, mp 116°; was prepd by nitration of H@==CH ; mw 202.22, N 6.9%; Ifts or
3,4-dinitro-6-bromodimethylaniline(Refs 2 & 4); Br.C-CH=C.COOH
N, 2,3, 6- Tetranitro-4-bromo-N-metbylaniline; prisms having 2 mols H20, loses w of crystn at
2,3, 6- Trinitro-N-nitro-4-bromo-N-metbylaniline or 100°, mp 182-3° , sublimes w/o decompn; fonms
numerous inorg salts; other props & methods of
(2, 3, 6-Trinitro-4-bromopbenyl)-metbylnitramine,
lt-yel ndls(from ale), mp 158° [ Forster & prepn are given in Beil
Coulson(Ref 4) give 165° ] ; was prepd by R ef: Beil 22, 44-5
nitrating 3-nirro-4-bromodimethy laniline(Refs 2 & 5-Bromo-nicotinyl Azide, 5.Bromo.3.pyridoyl
5) or 2, 5-dinitro-4-bromodimethyktniline or 2,3,6 Azide or Azido.5.bromonicotinic Acid,
-trinitro-4-bromodimethy laniline(Refs 2 & 4); and Br.C5H3N.CONa; mw 227.03, N 24.68%; CO1
N, 2,4, 6-Tetranitro-3-bromo-N-m etbylaniline; powdery ppt, mp 88-9 °(decomp), burns w/o
2,4, 6-Trinitro-N-nitro-3 -bromo-N-metbylaniline or defgrn; was prepd by diazotizing the hydrazide in
(2, 4, 6-Trinitro-3-bromopbeny l)-metbylnitramine, excess HC1. The hydrazide was prepd by refluxing
CO1 crysts(from chlf), mp 127°; was prepd by the Me ester of 5-b romo-nicotinic acid in alc with
nitration of 2-nitro-5-bromo-N-methy laniline(Refs hydrazine hydrate(Ref 2)
1 & 3). These ~compds are expl, but their expl Re/s: l)Beil-not found 2)R.Graf et al, JPrskt-
props were not detd Chem 138, 251(1933); BrA 1933A & CA 28,
Re/s.’ l)Beil 12, 771 2)Beil 12, [427] 3)].]. 769(1934)
Blanksma, Rec 21, 278(1902) 4)A.Forster & Note: There were sLso prepd the hydrazine &
W.Coulson, JCS 121 II, 1955(1922) 5)G.R.Clemo hydrazide derivs of bromopyridine carboxylic
& J .M.Smith, JCS 1928, 2422 acid. No nitro or nitrated detivs were found in
Beil or in CA thru 1956
Bromomethylbenzene. See Bromotoluene
Bromophenol and Derivatives
N.Bromo-N-methyl-ethylenedinitramine, Bromophenol(called Bromphenol in Ger),
Br.$1.CH2.CH2.~ .CH3; mw 243,05. N 23.05; OB to Br.C6H4.0H; mw 163.o2. Three isomers exist
N02 N02 and are described in the literature:
 B 315

2-B romopbenol, oil, having disagreeable odor, -5-bromophenol-sultonlc acid(?) with dil HzSO,;
bp 194°; 3-B rvmopbenol, lfts, mp 32-33°; and the K salt, (02N)3 Br.C6(OK).S03K, yel trysts
4-Bromophenol, crysts(from chlf or eth), mp 64° (from ale) isolated during the above prepn,
ZZe/: Beil 6, 197, 198, (104,105) & [183,184] expl when heated(Refs 1 & 3); and 2,4,6
Nitrosobromophenol, (ON)Br.C6H3.0H; mw -Trinitm-3-bromopbenol, COI lfts(from w), mp
202.02, N 6.94%. TWO isomers are described in 149°, non-vol in steam; was prepd by nitrating
the literature: 4-Nitroso-2-bmmop benoI, pale 3-bromophenol, 2-nitro-3 or 5-bromophenol,
yel to lt-bm ndls(from benz or w) or red ndls 4-nitro-3-bromophenol, 2,4- dinitro-3 or 5-bromo-
(from dil ale), mp 142-56°(dec)(Refs 1 & 3) and phenol or 2,6-dinitro-3-bromophenol with mixed
4-Nitmso-3-bromopbenol yel ndl.s(from eth+ petr HA03-H.J04(Refs 2 & 3). Both of the
eth), mp 139°(dec)(Ref 2); absoqxion spectra trinitro bromo derivs are expl compds but their
(Ref 4). Other props & methods of prepn are expl props were not detd
given in the Refs Refs: l)Beil 6, [ 283] ‘2)Bei1 6, 292 & [ 283]
Refs: l)Beil 7, 639 & [583] 2)Beil 7, [583] 3)H.H.Hodgson & F.H.Moore, J CS 1926, 160-1
3)H.H.Hodgson & D. E.Nicholson, JCS 1940, 811 Tetranitrobromophenol, (02N)4CeBr.0H; mw
(1940) & CA 34, 6590(1940) 4)P.Ramart-Lucas 353.02, N 15.87%. One isomer is described
et al, Br,dlFr 1948, 571 & CA 42, 7633(1948) in the literature: 2,3,4, 6-Tetram”tro.5
Dirzitmsobmmophenol, (ON)zBrC6H2.0H, not -bromopbenol or 2,4,5, 6- Tetranitro-3
found in Beil or in CA through 1956 .bromophenol, COI crysts(from chlf
or CC14),
Mononitrobromophenol, (02 N)Br.CeH3.0H; mw mp 157°, expl on heating to higher temp; gives a
218.02, N 6.43%. Ten isomers ate described in yel color in alc or w soln; was prepd by nitrating
the literatute(Ref I). Their props & methods of 5-nitro-3-bromophenol. Its other halogen analogs
prepn are given in the Ref are also expl
Re/: Beil 6, 243,244,(123) & [232,233,234] Refs: l)Beil 6, 293 2)J.J.Blanksma, Rec 27,
Dinitrobromophenol, (02N)JBr.C6H2.0H; mw 36(1908j & JCS 92 I, 126-7(1907)
263.02, N 10.65%. Four isomers are described in Bromophenyltriazene(called Bromphenyltriazen
the literature: 2,4-Dinitrv-3-bromophenol, yel in Ger), Br,C6H4. N: N.NH2; mw 200.05, N 21.00%.
ndls(from w), mp 175 °(Refs 1 & 6); 2,4-Dinittv-5 Thee isomers are known: 2-Bromopbenyltriazene,
-bromophenol, CO1 prisms(from alc or eth), mp trysts, expl when rubbed; 3-Bromopbenyltn”azene,
91.5-92°(Refs 2 & 6); 2,4-Dinitrv-6-bromopbenol, trysts, expl when heated and 4-Bromophenyl-
sulfur-y el prisms(from eth), almost col ndls(from ttiazene, Ifts(from gasoline), mp 36.5 °(de~~ on
w, alc or benz + gasoline), mp 117-20°, sublimes standing at RT it transforms into a compd
when heated carefully, explodes when heated melting at 39° but when r ecrystd(from eth + petr
rapidly(Refs 3 & 7); 2, 6-Dinitro-3-bmmophenol, et ) it again meIts at 36.5°; its Cu salt,
9
ndls(ftom petr eth), mp 131°, VOI on steam bath CuC6H~N3 Br, crysts(from epichlorohydrin), expl
(Refs 4 & 6); and 2, 6-Dinitro-4.brvmopbenol, in a flame or in contact with coned HN03. These
lt yel ndls(from w or ale) or orn-red prisms(from isomers were prepd by redu~on of the approp-
eth or AcOH), mp 74-83°, sublimes W/O decompn riate bromoazidobenzene with SnC12 in HC1 + eth.
when heated carefully(Ref 5). All of these The Stannic Cblon”de salt of each was unstable
isomers form numerous salts which ate colored expl
tryst compds, some of which ate unstable & R efs: l)Beil 16, (405,406) 2)0. Dimroth & K.
expl when heated(eg Ag salt). Orher props & Pfister, Ber 43, 2760-61(1910) & CA 5, 485-6
methods of prepn of these compds ate given in: (1911)
Refs: l)Beil 6, [249] 2)Beil 6, 261 & [249]
3)Beil 6, 261, (128)& [250] 4)Beil 6, [250] Bromopicrin, See Nitrobromoform under Bromoform
6)H.H..Hodgson & F. H. Moore,JCS 1926,158,159 and Derivatives
7)H.P.Crocker & R. H.Hall, JCS 1955, 4490 & CA
50, 10713(1956) 5-Bromo-3-pyridoyl Azide. See 5-Bromo-nicotinyl
Trinitrobromophenol, (02N)3Br.C6FI.0H; mw Azide
308. 64%. Two isomers are described in the
literature: 2,4,5 .Trinitm-3-bromophenol( ?)(called Bromoqui none. see Bromobenzoquinone
2,5,6-Trinitro-3-bromoph enol in Ref 3), trysts
(from w), mp 146°, vol on steam bath; was prepd Bromoresorcinol and Derivatives
by boiling the dipotassium salt of 3,4,6-trinitro Bromoresorcinol; Bromoresorcin; Bromo-1, 3
 1

B316

-aibydroxybenzene or Bromo-1 ,3-benzenedioI tube or in contact with a flame(Refs 1 & 2)

(called Bromresorcin in Ger), H0.C6H3Br-OH; R efs: 1 )BeiI 26, (109) & [ 197] 2) R. Stollg, Ber
mw 179,02. Three isomers exist: 2-, 4- & 62, 1123(1929) & CA 23, 4471(1929) 3)E.Lieber
5-bromo-resorcinol. They are described in Beil et al, JACS 73, 1793(1951) 4) E. Lieber et al>
Ref: Beil 6, 821, [819,820] Analchem 23, 1594(1954) 5)L.A.Burkardt & D.W.
Mononitrobromoresorcinol, H0.(02N)CeH2Br.0H; Moore, AnalChem 24, 1581(1952).
m w 234.02, N 6.00Y0. Only two isomers were
found in the literature: .S-Nitro-2-bromoresorcinol, Bromotoluene and Derivatives
orn-yel ndls(from eth acet + petr eth), mp 2010 Bromotoluene or Bromomethylbenzene( called
(dec)(Refs 1 & 2) and 6-Nitm-4-bmmo-resorcinol, Brom-toluol or Bromomethylbenzol in Ger),
crysts(from Ccla), mp 134°(Ref 3). Other PrOPs Br.CGH4.CH3; mw 171.05. Three isomers are
& methods of prepn of these compds are given in known: 2-Bromotoluene, COI liq, fr p -27°, bp
the Refs 180-2°, flash p 175°F, d 1.422 at 25 °(Ref 1);
Refs: l)Beil 6, [823] 2) G. Hellert Ber 56$ 3-Bromotoluerze, CO1 liq, fr p -39.8°, bp 183-4°,
1875(1923)& CA 18, 385(1924) 3)N.Kaneniwa, d 1.410 at 20 °(Ref 2); and 4-Bromotoluene,
JPharmSocJapsn 75, 785(1955)&CA 50,4842 wh crysts(from sic), mp 28°, bp 184-5°, flash p
(1956) 185°F, d 1.400 at 27°(Ref 3). The toxicity of
Dinitrobromoresorcinol, H0(02N)2C=HBr.0H; these isomers is not given in Sax(Ref 5) but it is
mw 279.02, N 10.04%. TWO isomers are found in Ref 4. Other props & methods of prepn
described in the Literature: 2,4-Dinitro-6 are given in Beil(Refs 1, 2 & 3)
.brornoresorcinol, yeI crysts(from AcOH), mp Re/s: l)Beil 5, 304, (153) & [234] 2)Beil 5,
89-90 °(Ref 1) and 4, 6-Dinitro-2-bromoresorcinol, 305, (154) & [235] 3)Beil 5, 305, (154) &
yel ndI <from ale), mp 189-93° with partial [236] 4)H.Staub in J.Houben, Edit,
subIimation(Refs 2,3 & 4). These compds form “Forrschritte der Heilstoffchemie”, Pt 2, VOI II,
numerous salts, some of which may be expl. Walter de Grrryter, Berlin(1932), 76 5)Sax( 1957),
They are, themselves, expl although their expl 389-90
props were not investigated Azidobromotoluene, N3(Br).C~H3.CHa; mw
Re/s: l)Beil 6, 829 & (405) 2)Beil 6, 829,(405) 212.06, N 19.81%. Two isomers are known:
& .[825] 3)G.P.Rice, JACS 48, 3130(1926) 2-Azido-5-bromotoluene, flakes, vol in steam;
4)G.Heller et d, JPraktChem 129, 211(1931); CA 4-Azido-2 or 3-bromotoluerte, CO1 liq which
2~ 2128-9(1931) & BrA 1931A, 477 solidifies on cooling. Other props & methods of
Note: Higher nitro derivs of bromoresorcinol prepn are given in B eil
#ere not found in Beil or in CA thru 1956 Ret: Beil 5, 333, 334, (163,164) & [ 255, 256]
Dinitrabromotoluene, (02N)2(Br).C6 Hz.CHa; mw
5- Bromo-l,2,3,4-tetrazole( caIl ed 5-Brom 261.05, N 10.72%. Eight isomers are known:
-tetrazol in Ger), Br. $. NH.~; mw 148.97, ‘N 2,3-D inr”tro-4-bromotoluene, CO1 ndl <from sIc),
N—N mp 129 °(Refs 5 & 7); 2,.5 -Dinitro-4-bmmotolu ene,
37.61%; CO1 CrY sts(from toluene), mp 147-8° straw-colored ndls(from ale), mp 111°(Ref 5);
(dec), tryst powd(from w) or ndls(from benz), 4,5-Dinitro-2-bromotolwne, CO1 Ifts(from ale), mp
mp 156°(dec); readily SO1 in hot ~C or eth; mod 94-5 °(Ref 6); 2,4-Dinitm-5-brDmotoluene,
sol in w with strong acid reaction; S1 SO1 in hot pale yel ndls or prisms(from ale), mp 103-4° or
ben~ the acidic dissociation constant is ndls(from ale), mp 114°(Ref 1); 2, 6-Dinitm-3
740 x 105(Ref 3); IR absorption spectra(Ref 4); -bromotoluene, rds or prisms(from ale), mp 86°,
X-ray diffraction data(Ref 5). It was first prepd vol in steam(Ref 2); 2, 6-Dinitm-4-bromotolu ene,
by heating cyanogen bromide(BrCN) with orn-yel ndls(from ale), mp 89-90 °(Refs 3 & 7);
hydrazoic acid in eth at 50-60° [Ref l,p(109)] 3,5-Dinitrv-2-brornotoIuene, yel cry sts(from ale)
and later by passing H2S into a HC1 soln of the or yel prisms(from eth + alc)~ mp 91-5°, VO1 in
CU salt of 5-bmmotetr~ole which was obtd bY steam(Refs 1 & 8); and 3,-5 -Dirzitru-4-brorrzotolu erze,
treating aq tetrazole-5-di azonium bromide with yel prisms(front HN03 or ale), mp 118°, VO1 in
finely divided CUO in 40% HBr. The diazonium steam(Ref 5). Other props & methods of prepn of
compd was prepd by treating an alkaline soln of these compds are giveo in the Refs, but their
5-aminotetra~le with NaNOz in a 40% HBr soln expl props were not reported
(Refs 1 & 2). The Cupic salt} grn cfysts> Re/s: l)Beil 5, 346, (169) & [265] 2)Beil 5,
detonated when rapidIy heated in a melting-point (169) & [ %~1 3)Beil 5, [ 265’1 4)Beil 5, 346&

.—..— --- ...—--—

_-— —.—. -.— — .—
1
 B 317

(170) 5)R.D.Kleene, JACS 71, 2259(1949) & CA Bronstein’s Explosives. Blasting expls which
43, 6992(1949) 6)J.K.Landquist, JCS 1953, consisted of AN 82.2* sugar 9 & iron pyrites 8.8%
2817 & CA 48, 11427(1954) 7)W.Qvist, (Ref 1); and NsN03 30-40, NS 25-55 & marble
ActaAcadAboensisMath et Phys 19, No 1, 3-I2 dust 5-45%(Ref 2)
(1953) & CA 49, 8992(1955) 8)P.J.C.Fierens et Re/s: l)J.B.Bronstein, USP 986900(1911) & CA
al, BullBelg 64, 658, 667, 696 & 709(1955) & CA 5, 1995(1911) 2)J.13.Bronstein, USP 988858
50, 11260(1956) (1911) & CA 5, 2179(1911)
Trinitrobromotoluene, (02N)3(Br).C6H.CH3; mw
306.04, N 13.73%. Only one isomer is described Brookhaven National Laboratory. A nationaI
in ‘the literature: 2, 4,6-Trinitm-3-bromo toluene, res earth center for fundamental and applied
CO1 ndls(from ale), mp 143-4°, sol in ale, insol research in nuclear sciences and related
in Iiqroin; was first prepd by nitrating 2,4dinitro subjects. It is an intergral part of the US Atomic
->bromotoluene and later by diazotizing 2,6 Energy Commission’s nationwide program. ,Like
-dinitro-3-bromo-4 -aminotoluene(Ref 1). Qvist other national labs of the AEC, Brookhaven is
et al(Ref 2) prepd this compd by nitrating the operated under contract by a private institution,
5-bromo deriv of o-cymene(isopropyltoluene) and Associated Universities, Inc. The governing
also by nitrating 2,4-din itro-5-bromoto1u ene( Ref body of this nonprofit educational institution is a
3). The trinitrobromotoluene is definitely an Board of Trustees made up of one scientist and
expl compd although no investigator has reported one administrative officer from each of nine
its ezpl props sponsoring universities: Columbia, Cornell,
Re/s: l)Beil 5, 349 & (174) 2)W.Qvist et al, Harvard, John Hopkins, MIT, Princeton, Univ of
AaaAcadAboensisMath et Phys 14, No 1, 3-36 Pennsylvania, Univ of Rochester & Yale. This
(1942) & CA 38, 5206(1944) 3)W.Qvist & M. huge scientific research establishment, which
Moilanen, ibid, N03, 9pp(1943) & CA 38, 5491 came into being in .1947, is Ioc ated on 3500acres
(1944) of scrub oak and pine in the center of Long
Island, some 65miles east of New York City
Bromotoluidine. See Bromomethylaniline Research at Brookhaven may be summarized
under four general headings: Studies o/ Atomic
3(or 5)-Bromo.l,2,4-triazole [called 3(or 5)-Brom Nuclei, Effects of Radiation upon Matter,
- 1.2.4-triazol in Ger] , H$-NH-N or Br.$-NH-N ; Radioisotopes and Other Nuclear Tools G
N—~.Br N— ~H Nuclear Technology. At present the Laboratory
mw 147.98, N 28.39%; COI prism s(from benz or w), employs more than 2100 persons, 400 of whom are
mp 188-9°; readily sol in w; diffc sol in benz or scientists and 700 are technical persomel.
eth; almost insol in chlf or eth acet; was prepd by Each year in the Fall, Btookhaven holds a
treating 5-nitrosaminbl, 2,4-triazole-3-carboxylic public visitor’s day. Admission is by ticket only;
acid with aq HBr(Refs 1 & 2). The expl props of applications should be made to Director’s Office,
this compd were not investigated Br~khaven National Laboratory, Upton, Long
Re/s: l)Beil 26, 21 2) W.Manchot & R.Noll, Islan~ NY
Ann 343, 9(1905) & JCS 90 I, 213(1906) Re/s: l)D.J .Hudges, “The Nuclear Reactor as a
Research Instrument”, SciAm 189, No 2, 23-9
Bronnert and Schlumberger patented in England ( 1953) 2)R.A.Beth & C. Lasky, “The Brookhaven
(1896) a method of gelatinizing NC by methanol or Alternating Gradient Synchrotrons”, Science 128,
ethanol mixed with small quants of org acids No 3336, 1393-1401(1958) 3)D.Puleston, Head,
(oxalic, citric) or their esters Information Division, “Brookhaven National
R e/: Daniel( 1902), 85 Laboratory---Present and Future Growth’’(June
1961) 4)Numerous booklets & pamphlets
Bronolithe. An expl invented by El. de Brones available to the public, issued by the Information
and patented in Germany( 1885), consisted of: Division of the Directors Office, Brookhaven
KN03 20-40, double picrate of Ba & Na 15-30, National Laboratory
picrate of Pb & Na 8-30, picrate of K & Na 2-10,
nitronaphthalene 5-20, sugar 1.5-20, gum 2-3 & Brougère Powder. See Brug~re Powder
Iampblack 0.5-4%
R ef: Daniel(1902), 85 Brown Charcoal. A product made by slightly
carbonizing rye straw and used in the manuf of
 B 318

Brown Powder, described under Black Po waler Pa( 1948), 22-6,323-30,338-54 & jf 4-s la) Anon,
Modifications ‘ ‘Small Arms Mat~riel and Associated Equipment”,
TM 9-2200( 1949), 23,53-58 & 58-65 2)G.M.Chinn,
Browning, John Moses( 1855-1926). Amer ~ventor ‘ ‘The Machine Gun”, USGovtPtgOff, Washington,
specializing in automatic small arms. Beginning 25, DC, VOI 1(1951), 156-86, 327-44 & 531-6
in 1879 he secured a patent for a breech-loading 3)W.H.B.Smith, ‘ ‘Rifles”, VO1 2 of NRA Book of
rifle(sold to the Winchester Co) and until his Small Arms, Military Service Publg Co, Harrisburg,
death he designed many types of rifles, pistols, P a( 1952), 66 4)W.H.B.Smith, “Pistols and
machine rifles and machine guns. In 1890 a MG Revolvers”, Vol 1 of NRA Book of Small Arms,
of his design, but known as the Colt, was Military Service Publg Co, Harrisburg, Pa(1953),
adopt e d by the US Army. His first automatic 27,132,216,228 & 368 5)Glossary of Ord(1959),
pistol was patented in 1898 but it was not manufd 50 6)W.H.B.Smith, “Small Arms of the World”,
in the US due to lack of financial support or The Stackpole Co, Harrisburg, Pa(1960), 160
interest. He then went to Beigium where the
famous FN(Fabrique Nationale) at Herstal-Li~ge Brown(or Cocoa) Powder. See under Black Powder
began to manuf his automatic pistol, as well as Modifications
his later automatic rifles & other weapons
(See also Browning’s Weapons) Brown’s Dynamite. A~J.Brown patented in
Re/s: l)G.M.Chinn, “The Machine Gun”, Vol 1, England( 1899) a dynamite having the following
USGivtPtgOff, Washington, DC(1951), 156-86 compn: NG 30; KN03 40, MgS04 24, collodion
2) EncyclBritannica, Vol 4(1952), 275 3)W.H.B. cotton 1, turpentine 4 & Na2C03 1%
Smith, ‘ ‘Pistols & Revolvers”, Vol 1 of the NRA Re/: Daniel(1902), 85-6
Book of SmaU Arms, Military Service Publg Co,
Harrisburg, P a(195 3), 27 & 132 4) W. H. B.Smith, Brown’s Powder. An expl adapted for blasting,
“small Arms of the World”, The Stackpole Co, and also proposed as a rifle proplnt, consisted of
Harrisburg, Pa(1960), 153-61 a soln of rosin in linseed oil 8-10, NaCIO~ 70-6%,
finely divided carbon(prefersbly Iampblack) 4 &
Browning’s Weapons. Many weapons were wheat flour 14-22 parts. The mixt was pressed and
invented by J, M. Browning, but not all of them broken into grains
were manufd under his name. Some of them were Re/: J.M.Brown, USP 1218976( 1917)& CA 11,
known as Colts, Winchesters, Remington, etc. 1 549(1917)
Following is a partial list of Browning weapons
m anuf d during the 20th century: Broyage(Fr). Grinding, crushing or pulverizing
a) Pisto 1s, A ritom ati c. Calibers .32, 9mm ~d
. 380; manufd primarily by the FN, Herstal Broyage de Poudre Noire(Fr). Grinding of BkPdr.
-Li &ge, Belgium; used beginning 1908 by the US The method used in France before WWII is
Army(Ref l,pp 22-6 & 374-7 and Ref 4,pp 216, described in Pascal(1930), 201
228 & 368)
b) Ri/les, Automatic, Cd .30, Model 1918 ~d Brugère Powder. A proplnt used with some
1918A1, known as BAR, adopted during WWI by success in Fran~e for the Chassepot rifle. It was
the US Army; was modified in later models(Ref prepd by grinding together, pressing and
l,pp 323-30 & Ref 3, 66; Ref 2, 173-6, 185) granulating as in the manuf of BkPdr, a mixt of
c)Machine Rifles. Cal .30, Model 1918A2 and Amm picrate 54 & KN03 46%. lt was more
Cd 7.6~mm, Belgian, MP34(Ref 1, 330 & powerful than BkPdr and gave less smoke
377-8; Ref la, 23 and Ref 2, 174 & 185) R efs: l)Daniel( 1902), 86 2)Marshall 1(1917),
d)Macbine Guns. Cal .30, Model 1917 & 1917A 284 3)Davis(1943), 51 4)P~rez Ara(1945), 223
and later modifications; Cd .50 M2MG ~d 5)1220, Pirotechnia(1950), 212
1 ater modifications(Ref 1, 338-45 & 346-54 Ref
l% 53-58 & 58-65 Snd Ref 2, 161,164-5,167-72> Brunswig, H(1865- ?). Ger scientist special-
177-86 & 327-44) izing in expls. He is the author of the books;
e)Browning Aircraft Cannon Cd 37mm(Ref 2, C‘Explosives”, Wiley, NY(1912)(English
531-6) translation by Munroe & Kibler) and “Das
Re/.s: l)W.H.B.Smith, *gSmall Arms of the Rauchlose Pulver” , W. de Gruyter, Berlin(1926)
World”, Military Service Publg Co, Harrisburg, & numerous other publications on expls and re-

. ...— ------- -– —--——-————— —

 B 319

lated items pressure curve, Brynk proposed his own empirical

formula
Brunswig’s Test(Loss in Weight at 1100). ,A Ref: M. E. Serebry akov, “Interior Ballistics”,
heat or stability test applicable to gelatinized originally published in Moscow(1949) and
smokeless powder translated into English by Dr V. A. Nekrassoff
Procedure: An accurately weighed 5-g sample is (1950), Abridged E~tion, PP 3,27 & 32(Contract
spread in a thin layer in an open$ shallow dish NOrd 10260)
and heated for 72 hrs in a special oven, fitted
with a revolving stand. Then the dish is cooled BSI Sieves(British Standard Institution Sieves).
in a desiccator and weighed. The loss in w is A series of fine mesh, std test sieves of
crdcd as percentage of original wt. The sample specification governed by British Standards Spec
is then reheated for an 8-hr period each day(for 6 NO 410-1943, available from BSI, Victoria St,
to 8 days), reweighed and the loss for each 8-hr London SW1. These sieves with their mesh
period is calcd as % loss(Refs I, 2 & 4) numbers & openings are compared with TJ&
Data for losses in wt(for each 8-hr period Tyler & German std sieves in Vol 1, Table I, p
studied) of well and poorly stabilized powds 674 of this Encyclopedia
contg 22.5% NG and 65% NC & other ingredients
are given in Ref l,p 402. ,During the first 72 hrs BSP Powder(Poudre B, Si~ge et Place]. A powd
all powds showed regular losses averaging 1 to previously used in France for siege howitzers
1.5%. Subsequent losses of poorly stabilized Re/: Marshall 1(1917), 297
powds increased to 2-2.5% per 8-hr period, while
well stabilized powds continued at ca 1% per day. BSQ. A modified double-base propellant developed
After heating for ca 176 hrs, the poorly stabilized at ABL. Its compn & props are given in conf
powd losses amounted to 42%, while for well “Propellant Manual”, SPIA/M2(1959), Unit No
stabilized powds the losses were 18-20% for a 519
192-hr heating period
Metz(Ref 3) compared Btunswig’s Test “B.Stoff”. According to RocketEncycl(1959), 59}
method with other quantitative stability tests(such this is a code name for hydrazine hydrate,
as Mayrhofer, MayrhoferWill, Hansen md the 85° H2N,NH2.H20, one of the Ger rocket fuels used
& 1100 Hydrolysis Tests) and with qualitative during WWIL The same code name used during
tests(such as Abel & the 134.5° Heat Tests). WWI for Ger Iachrymator Bromoacetone(qv)
Brunswig’s method is indicated to be applicable
only to extremely stable powders. For example, if BSX. A code designation for the expl 1,7
a powd is of moderate stability and just passes -Diacetoxy-2,4 ,6-tetramethylene-2,4 $-trinitramine
other quantitative tests, it might not pass (qv)
Btunswig’s Test. On the other hand, if a powd
passes Bmnswig’s Test it usually passes other BTM. A castable HE compn contg Tetryl 55,
quantitative tests but may not pass qualitative TNT 25 & Al 20%. Its cast d is 1.77 and relative
tests, such as Abel’s, Zinc-Iodide-Starch Test & fragmentation efficiency 140% TNT
others Ref.’ S.Fleischnick, PATR 1595( 1946),p 2 &
Refs: l)Btuflswig, ProPs(1926), 339& 402 2) ‘table 1
Ulhnann, VO1 4(1929), 748 3)L.Metz, SS 27,
150-3 & 188-91(1932) 4)Rei11y(1938), 86 BTNEN. Abbr for Bis(2,2,2-trinitroethy l)-nitramin%
which is designated as HOX. Same as’ Di(trinitro-
Brynk, A. F.(1855- ?). A professor at the ethyl)-nitramine, listed und et Diethyhunine and
Russian Attillefy Ac~emy, know for his wo~ On Derivatives
ballistics. His course on ‘tInterior Ballistics”,
published in 1901, was translated into German BTZ. A series of French army missiles developed
and in 1902, at the request of the US Navy Dept, by the Bureau Technique Zbrowski in Brunoy,
was translated by J .B.Bemadcm(qv) into English Seine. et Oise, France. Among them are BTZ
for publication in the USA(1904). In 1898-1901, 412-O l(Ogre I), BTZ 411-Ol(Lutin), and BTZ
Prof Btynk & Prof N. F. Drosdov extended Sarrau’s 420-0 l(Naine Be%&)
Ref: G.Merrill,
t~DicU~n~ of Guided Missiles
formula for the combustion of BkPdr into the
domain of smokeless NC proplnts. For the and Spate Flight”, Van Nostrand, NY(1959), 103
 1

B 320

Bubbles of Gas in Explosives, The presence of The final blend consisted of 10 lb of mixt 1, 10 lb
minute gas bubbles(such as air bubbles) which mixt 2 and 5/16 lb powdered charcoal; it was
are trapped in liquid, plastic, gelatinous or solid claimed that charcoaI exerted a most favorable
expls, greatly increases their sensitivity to influence on the action of the expl
detonation by impact. This increase in sensitivity Refs: l)C.U.Buck, USP 940580(1909) & CA 4,
is attributed to adiabatic compression and heating 514(1910) 2)Colver(1918), 324
of the entrapped bubbles. This phenomenon was
investigated in England by Bowden et al Budenberg’s Explosive. A biasting powder: Na
Reis: l)F.P.Bowden et al, Narnre 157, 105(1946) nitrate 40, K nitrate 38, sulfur 12 & charcod 10Y.
& CA 40, 2306-7(1946) 2)F.P .Bowden et al, Re/: Pepin Lehalleur(1935), 287
PrRoySoc A188, 291-311(1947) & CA 41, 3627
( 1947) 3)F.P .Bowden & A. D, Yoffe, “Initiation Buechert, of San Francisco, CaIif, patented in
and Growth of Explosion in Liquids and Solids”, 1894 an expl compn consisting of NH4C103,
Cambridge UnivPress, Cambridge, England(1952), (NH4)2S04, NsN03, NG & woodpulp. In order to
29-63 prevent the reaction in storage betw
(NH4)2S04 & NaN03, the trysts of these compds
Bubbles of Gas in Liquid Explosives. Suppression were preco ated with Al oleate
of Bubble Initiation. It has been shown(see R ef: Daniel( 1902), 87
previous item) that one of reasons for the increase
in sensitivity of expls to initiation by impact is Bührle, Emil Georg( 1890-1956). Swiss engineer
due to the adiabatic heating during sudden specializing in ammunition and weapons. Formerly
compression of small trapped gas bubbIes. Gray & Director of the internationally known
Yoffe(Ref 1) stated that initiation occurs as a ‘ ‘Werkzeugmaschinen fabrik Oerlikon. Buhrle & Co”,
result of the burning of explosive vapor in the gas Switzerland
phase prior to decompn of the liquid, such as NG R efs: I) Anon, Explosivst 1957, 1 l(a brief
In order to reduce the fire and expln obituaty) 2) ’’Oerlikon Pocket Book”, Ziiich
hazard in pressing, rolling and extmding certain -Oerlikon( 1958), 13
thermoplastic expls contg liq expl s(such as NG)
due to the adiabatic compression of entrapped Buildings and Other Structures at Ordnance
Establishments. Any plant, works, arsenal,
gases, it has been proposed by Jones(Ref 2) to
incorporate in formulations some volatile depot, proving ground and other activity formerly
under control of the US Chief of Ordnance may be
substances to seine as inhibitors. Jones stated
considered as an Ordnance Establishment
that ideal expln inhibitors are complex org vapors
which dissociate endotherm ally below the The area occupied by such an establishm~t
ignition temp of the expl compn and thus absorb generally includes the following buildings and
heat and reduce the expln potential. The quantity other constructions:
of inhibitors added to NG(or other Iiq expls) will A)Administration Buildings or any other adminis-
be detd by their heat-absorbing power and vapor trative offices which function for the establishment
as a whole in contrast to field of/ices(qv)(Ref 1,
pressure. The names of these inhibitors are not
seen 8 and Ref 2, seen 2,p 1)
revealed in Ref 2
B) Operating Buildings(except magazines) in which
Re/s: l) P.Gray & A. D.Yoffe, Research(London)
operations pertaining to manufg, processing or
2, 339-40(1949)& CA 43, 8139(1949) 2) E. Jones,
Nature 173, 77-8(1954) & CA 48, 5499-5501(1954) handIing expls, ammo or ammo components are
performed. A group of bldgs used to perform the
Bubble Period Measurements(Used for BubbIe consecutive steps in the manuf of processing of
expls or ammo is called an operating line. For
Energy Measurements). See under Underwater
example, in the manuf of TNT, the buildings,
Explosions
known as mono-, hi-, and tri-(nitration) houses,
which are followed by purification, flaking and
Buck’s Explosive. An expl compn obtained by
blending two mixm previously prepd in separate packing houses, consitiute a “’line’y( “TNT line”)
(Ref 1, seen 8 and Ref 2, seen 2,p 10)
kettles. Mixt I was prepd by fusing together SO
parts PA & 50p DNPh to which was later added C)Auxiliary Buildings supplement operating
buiIdings, Iines or areas, but which are not
4p collodion cotton. Mixt 2 was obtained by
directly utilized for the production activity
blending at 130° 50p B a nitrate with 4-5p paraffin.

—..-
1’
 B 321

Following are examples of such bldgs: and sewage, necessary for the operation of an
a) Field Office is a bldg housing offices of establishment(Ref 2, seen 2,p 16)
administration personnel responsible for a part H) Durmage Yard is an open air space for storing
of the establishment, such as one of the operating the reserve supply of lumber for an establishment
lines (Ref 3,p 140)
b)Buildings for storing acids, inert components I)Holding Yard is a group of RR tracks used to
and materials(such as toluene, hexamthylene- store cars of expls, ammo or inert materiaIs for
tetramine, cellulose, etc) used in the manuf of indefinite periods. The yard may also include
ezpls. The area in which these bldgs are ateas for storing or parking trailers contg expls
situated may be called inert area and ammo(Ref 2, seen 2,p 6 & Ref 3,pp 54 & 141)
c) Service Magazines used for intermediate J) Classification Yard is a group of RR tracks
storage of expls or ammo, not exceeding the used for receiving, shipping and switching cars
minimum amt necessary for manufg operations contg expls, ammo or inert materials(R ef 2, seen
d)Packing and Shipping Houses 2,p 3 & seen 17,p 14 and Ref 3,p 53)
e)Power House and Electrical Substations K) Loading Docks ate facilities at ground level or
f)Pump, Valve, Compressor or Fan houses; Fire elevated structures designed and installed for
House transferring ezpls, ammo and inert materials
g)Laboratory, such as Chemical, Physical or between automotive vehicles and RR cars(Ref 2,
Ballistic seen 2,p 7 & seen 17,p 16 and Ref 3,pp 54-5)
h) Surveillance Buildings for Explosives or L )Gasoline czrzd Other Liquid Fuel Tanks should
Ammunition be located at distances ranging from 100 to 1800 ft
i)change House with facilities for employees to depending on the bldg classification because they
change clothing, bathe, etc are fire hazards(Ref 2, seen 17, p 18 & seen 24,p
j)Guard House? Bombproof Building and other and Ref 3,pp 55-6)
Personnel Shelters M)Restricted Area. Some Ordnance establishments
(Ref 1, seen 8 and Ref 2, seen 2,P 2) may contain a fenced area where the entrance and
D)Magazine Buildings specifically designated for egress of personnel and vehicular traffic are
the storage of expls, ammo or loaded components controlled for reasons of safety and security(Ref
Following types of magazines may be 2, seen 2,p 12)
found in Ordnance establishments: All the above-mentioned bldgs and other
a)Igloo(barrel or arch) type structures within US Ordnance establishments
b)Box(earth-covered, reinforced concrete) type shall be located at such distances, one from the
c) Stradley(Yurt)( earth-covered, reinforced other, as prescribed by Quantity-Distance Tables
concrete)type with vertical sidewalls and arched given in Ref 2, seen 17 and Ref 3,pp 448o
roof The quantity of expi material and distance
d)Corbetta(eatth-covered, beehive or dome) type separation relationship which provide defined
e)Aboveground types, include the magazines types of protection are based on levels of risk
originally named: Ammunition Magazine, Black considered acceptable for the stipulated exposures
Powder Magazine, Primer & Fuze Magazine and Ref.s: I)US Chief of Ordnance, “Safety and
Smokeless Powder Magazine Storgage Manual for Explosives and Ammunition”,
f)Richmond type(two sides and rear are barricaded) PP Form No 5994, Washington, DC(1928), seen 8
also belongs to aboveground types 2)US Ordnance Cofps Manual Ord M 7-224,
g)Hillside type ‘ ‘Ordnance Safety Manual”, Washington, DC(1951)
h)Subsurface type(all portions underground) 3)US Dept of the Army Technical Manurd “Care,
(See Ref 2, seen 2,PP 7-9 & seen 18, alSO Ref 3)PP Handling, Preservation, and Destruction of
22-35 & 36-50) Ammunition”, TM 9=1903, Washington, DC( 1956)
E)Inhabited Buildings occupied in whole or in 4) B.Kanouse & C. V. Ruskewicz, PicArsn, Dover,
part as a habitation for human beings or where NJ; private communication(1961)
people are accustomed to assemble
‘F) Barricades, Natural and Builtup; installation Built-up Detonation. See under Detonation
Boundaries, See Barricades
etc. in this vol as
well as in Ref 2, seen 17, pp 24 & 32 and in Built-up Guns. One of such weapons was the
Ref 3,pp 35 & 108 Brit breech-loading gun invented ca the beginning
G) Utilities, such as water, air, steam, electricity of the 16th century. Its b,arreI was fashioned by
 B 322

welding mgeher b=s of iron to form sn open This improved pdr was known as Collodin. The
cylinder. The powder chamber was separated from next improved bulk pdr was EC Powder, patented
the barrel, and before firing, was screwed into in 1882 by the Explosives Co of Stowmarket,
it by means of an uninterrupted thread. Some of England. It consisted d nitrated cotton( 12.5
these guns were used in 1588 by the Brit Navy -1 2.8% N) mixed with K & B a njtrates and a
against the Spanish Invincible Armada(Ref 3). The small amt of dye. It was made into grains which
so-called “leather” gun, invented by Wurmbrandt were then partially gelatin ized with eth-alc.
of Sweden and used by the Army of Gustavus Some later pdrs contained Ba nitrate but no K
Adolphus(beginning of the 17th centufy), consisted n itra te. Ba nitrate has the a dv antage of being
of a copper tube bound with iron rings ~d ropes non”-hydroscopic and practically smokeless, but
and covered with leather. In some later built-up it has the ~awback of leaving a residu?~ in the
guns, wire was neatly wound ground the b~rel at gun barrel, which is difficult to remove. A
high tension(Ref l,P 61 & Ref 2,P 83) small propn of vaselin or paraffin wax was some-
A modem built-up gun consists of two or times added to moderate the rate of burning.
more concentric cylinders assembled by shrinkage. Starch was used occasionally as a binder and
In a two-piece gun the outer cylinder, the jacket, camphor to improve gelatinization. Some pdrs
is heated and slipped over the inner cylinder, the contained nitrated benzene or toluene which
tube. As the jacket cools, it fits snugly over the served as moderators of burning and as auxiliary
tube. This process compresses the inner tube and gelatinizes. Lampblack, woodmeal, various gums
the elastic strength of the gun is considerably & K ferrocyanide were also used as ingredients,
increas e d. Another advantage of built-up gun is and a small quantity of powdered chalk was added
the removability of the inner tube, or liner, when for stabilization. Some pdrs were graphited(Refs
its rifling wears out(Ref 2,p 84). The 240mm 1,2,3,4 & 5)
Howitzer, briefly described in Ref l,p 156, may According to Thorpe(Ref 4,p 528), in the
be cited as example of such guns prepn of bulk pdrs the mixts of NC with other
Re/s: l)Hayes(1938), 61-4 2) J. R. Newmm, “The ingredients are granulated prior to their treatment
Tools of War”, Doubleday, Doran & Co, NY( 1943), (mo~tly on the surface) with a solvent. In order
83-4 & 156 3) J. F.C.Fuller, “A Military History of to granulate the mixts, they are sprinkled with
the Wasetern World”, Funk & WagnaHs, NY, Vol 2 water and then either placed in a rotating drum or
(1955A 11 spread out on a rapidly oscillating table. Another
method is to slightly compress the moist mixt and
Bulgarian Armament. No information at our then to break it up into grains which are screened
disposal and dried. The original standard Brit chge for
sport ing cartridges was 42 grains, but later the
Bulk and Condensed Powders(Sporting Smokeless 33-grain chge became more common. There are also
Propellants). Sporting smokeles .s proplnts have 38-, 36- and 30-grain charges(Ref 4,p 528). The
now nearly completely replaced black powders gelatinization of NC in the 30-grain pdrs is nearly
because they have the following advantages over complete which makes them similar in nature to
BkPdrs: smokelessness, smaller recoil and less condensed pdrs(see below)(Ref 2,p 83). Arnben”t,
noise. Sporting smokeless proplnts may be EC, Heruite, imperial Scbultze, Kynocb’s Smokeless,
divided into bulk and condensed types. Bulk Ruby and Smokeless Diamond are examples of
pdrs are faster burning than condensed pdrs and European bulk pdrs
have a lower density Davis(Ref 5 ,pp 289-92) describes the method
The original bulk pdrs were prepd so that of preparing US bulk pdrs having the following
the chge for a 12-gage shotgun would occupy the compns :NG(l 2.9-13.15% N) 84-89$ K nitrate
same space in the paper carrridge(of 2.5” normal 6.0-7.5, Ba nitrate 2.0-7.5, starch 0-1.0, paraffin
iength) as the standard chge of 82 grains of oil 0-4.0 & DPhA 1.0%. The microscopic appearance
BkPdr occupying a space of 3 liq dratns( 10.65 ml). of a bulk pdr manufd by Western Cartridge Co(now
The first pdr of this kin4 that of a German Officer Olin-Mathieson Chemical Co) is given in Ref 5,p
Schultze(1864), was prepd by nitrating WOOd 288
fibers and then impregnating them with a soln of The condensed pdrs have higher density
KN03 alone or with BS(N03 )2. A better pdr was than bulk pdrs and the charge occupies only
obtaned in Austria(early 1870’s) by partially 1/3 to 1/2 the volume of a BkPdr chge. These
gelatinizing nitrated wood with ether-alcohol. pdrs consist of completely gelatinized NC with
 B 323

practically the same additives as used in bulk upon any static pressure that may be present, a
pdrs. They are manufd by methods similar to s inusoidall y varying strain of the same
those used for flake rifle proplnts. Briefly frequency will occur. The ratio of these
described, the gelatinized pdr mixt(paste) is sinusoidal amplitudes is called the dynamic bulk
rolled into thin sheets which are cut into small modulus. The quantity will vary to some extent
flakes and dried. The requisite rate of burning is with frequency due to the finite time required to
obtained by adjusting the size and shape of the reach thermal and structural equilibria. When
grains(Refs 1,2,3 & 4) dissipation of energy occurs during deformation
One of the great disadvantages of condensed of the material, the strain will lag behind the
pdrs is that, due to their small bulk, they require stress by an angle 8
special cartridge cases with a cone of pasteboard The apparatus used by Cramer(Ref 5) ~.r
to fill up part of the base. Otherwise the case dynamic modulus measurements was that devised
would not be entirely filled. Because of the small at the US Naval Ordnance Laboratory by Sandier
space occupied by the pdr chge,very slight (Ref 2). This apparatus is actualIy a modification
variations in the strength of the cap and other of one described by Meyer & Tamm(Ref 1). The
conditions could produce great variations in the instrument used by Cramer is shown schematically
pressure generated. The gun might therefore be in Fig I,p 2 or Ref 5
strained dangerously and difficulties are sometimes From data obtained with this apparatus, the
experienced in extracting the cartridge cases. value of K may be calcd from the following
In loading cartridges, the pdr is ‘always measured equation: K=— Pc*fevl —, where p is the density
by volume; the higher the d of the pdr, the greater Vaf(l + V2)
is the error in wt due to slight differences in vol. of water(g/cm3); C the velocity of sound in water
For these reasons bulk pdrs are usually preferred in the tube of the apparatus(cm/see); f. the
to condensed pdrs. Cannonite, Shotgun Rif~eite resonance frequency of the water column with no
and Sporting Bullistite are examples of European sample present(cps); V 1 the volume of the
condensed pdrs. Indurite of Munroe is an example sample(cm3); V the VOI of water in the tube(cm3),
of an Amer condensed pdr(Refs 1,2 & 4) ~f the frequency shift in the resonant frequency
Ger sporting pdrs are listed by Brunswig after insertion of the sample(cps) and q the
(Ref 3,p 134) quantity known as rhe “10ss factor” or “10ss
According to Thorpe(Ref 4), some sporting tangent”, ie, q=tan & As the value of q is very
pdrs are made as follows: the grains are small(less than O. 1) for rigid materials, such as
thoroughly gelatinized and, while they are still cast -or highly compressed HE’s no attempt was
wet with solventt treated with steam. This causes made to determine its value and q was assumed
rapid evaporation o f solvent, leaving the grains to equal Zero
in a state which is intermediate between that in The following table gives the bulk modulus
bulk and condensed pdrs data(K) for several HE’s and wax at temps of
Refs: l)Marshall 1(1917), 322-35 2)Barnett(1919), 25-30° as detd by Cramer(Ref 5,p7):
82-7 3)Brunswig( 1926), 134-5 4)Thorpe 4(1940), Table
528 5)Davis(1943), 287-92 Material Density Bulk Modulus
x 10-’0
Bulk Compressibility. See Bulk Modulus and dynes/cm2
Bulk Compressibility
Corn B-60/40 1.72 4.14
Bulk Density. See under Density (wn“{ RDX 75
micron size)

Bulk Modulus and Bulk Compressibility. According CyCIOtO1-75/25 1.74 3.09

to Cramer(Ref 5 ,p 1), one of the important constants TNT 1.56 2.92
of an isotropic elastic solid is the bulk modulus 3.56
Corn B(RDX 62.5 -
(K) or its reciprocal the bulk compressibility(B). TN+’35.6 & wax 1.9%)
The K is defined as the ratio of stress to strain 1 l 68 2.34
Corn B(RDX 61.9,
when the stress is a pressure applied equally on TN+’35.6 & WSX 2.7%)
all surfaces of the sample and the strain is the
PETN 4.6o
resulting change in volume per unit volume. If a
sinusoidally varying pressure is superimposed Wax 0.91 2.96
 B 324

The bulk compressibility(B) is calculated from Bullet Fit(or Jump) Test. See under BULLETS
the equation B= ~/K TESTS
For description of an apparatus used by
Philipoff & Bro dnyan, see Ref 3, and of that Bullet Impact Test(Rifle Bullet Test). See under
used by McKinney et al, see Ref 4 BULLET TESTS
Re/s: 1 )E .Meyer & K. Tamm, AkustZeitschr 7,
45-5(J(March 1942), “An Accustic Method for Bullet Penetration Test. See under BULLET
Determining the Dynamic Compressibility and TESTS
Loss Factor of Elastic Substances” 2)C.S.
Sandier, NAVORD Rept 1524(Sept 1950), “An Bullet Pull Test. See under BULLET TESTS
Accoustic Technique for Measuring the Effective
Dynamic Bulk Modulus of Elasticity and BULLETS
Associated Loss Factor in Rubber and Plastics” A bullet or “small ball’ ‘(from the French
3)W.Philipoff & J. Brodnyan, JApplPhys 26, 1‘boulette” ) is a projectile(missile) which is
846-9( 195 5), ‘ ‘Preliminary :Results in Meas~ing discharged from a small firearm, such as a
Dynamic Compressibilities” 4)J .E.McKinney pistol, revolver, shotgun, rifle, machine gun, etc
et al, JApplPhys 27X 425-30(1956), ‘Apparatus Histotical(Refs 1,4,5,9,10 & 12). The
for the Direct Determination of the Dynamic first infantry firearm was invented ca 135o,
Bulk Modulus’ ‘ 5)W.S.Cramer, NAVORD Rept about 100 years later than the cannon. This
4380(Sept 1956), “Bulk Compressibility Data primitive small arm was called “baston-h-feu” in
on Several Explosives” 6) J. Alster, PicArsn, Fr and band-gun in Eng. It was a simple iron
Dover, NJ; private communication(1961) tube attached to a Iong$ straight wooden stock.
The butt end of the tube was closed and
Bulk (or Volume) Strength of Explosives. Same provided with a “touchhole”, bored from the
as Cartridge Strength. See under Strength of exterior. The charge Y consisting of- BkPdr, a wad
Explosives and one or several bullets$ was introduced
through the muzzle and fired by thrusting a
Bulldog Brand Powder. A safety mining expl: heated wire through the touchhole. The wire
KN03 83,5-86.3, sulfur 13-14 & charcoal 1-2.5%, was tioon(ca 1405) supplanted by a <‘time
patented in England by Curtis et al in 1899. A match” or simply a “match” which was a
fairly large propn of S and a small propn of C string of cotton or hemp boiled in saltpeter or
were proposed in order to lower the temp of the lees of wine. The primitive bullets were
combustion and to prevent formation of CO and either stones or metallic slugs( shots) of irregular
K2S sizes and shapes. The same kind of slugs were
Re/: Daniel( 1902), 87-8 used in the first cavalry firearm, which was a
half-sized handgun attached at its butt end to a
Bulldog Missile. A US Navy air-to-surface long stock. During firing the gun rested on a
missile powered by a solid proplnt. The missile forked stand poised on the saddle, while the end
was developed by the Glenn L. Martin Co as a of the stock was held against the chest. Its
successor to the Bullpup Missile. It has a name, poitn”nale was derived from the Fr
greater range than the Bullpup and can carry a “poitrin”, which meand chest. This weapon,
nuclear warhead if requited also called petronel, was the predecessor of
R e/s: l)G.Merrill, “Dictionary of Guided Missiles pistol and carbine(Ref 12b,p 125). The
and Space Flight”, Van Nostrand, NY(1959), 104 arquebus(see VO1 1,p A488-L ) improved the
2)Glossary Of Ord(1959), 50 3)C. E. Davis, “The handgun by having a bent stock easily fitting the
Book of Missiles”, Dodd$ Mead& Co, NY(1959), shoulder of a man, instead of a straight stock;
30 the butt end of the improved stock was held
under the armpit. At first, the same kind of
Bulldog, Special. A Brit permitted expl patented slugs as were used in the handgun were used in
ca 1901: KN03 84-6$ charcoal 12-13, basic Mg this weapon, but these were later replaced by
carbonate 2.5-3.5 & moistute(max) 27.. It was small cast spherical lead slugs(balls). As early
used in compressed form at a density not higher lead balls were smaller than the bores of
than 1.45 arquebuses(which were of different calibers)>
Re/: Daniel( 1902), 88-9 considerable portions of the powder gases
 B 325

escaped through the muzzle thus lowering the reduction in size of muskets
pressure behind the ball. This caused short Although rifled firearms were invented in
-range and inaccurate’ firing in all early firearms the 1st quarter of the 16th century, practically
When the caliber of the arquebus was no nation used them because with round bullets
standardized as in C‘arquebus of caliber”, they offered very little advantage over the
better known as caliue~bore diam ca 3/4”), smooth-bore arms unless the balls were rather
the balls were cast of nearly the same diam as tightly fitting. The rifled firearms became of
the bore of caliver. Standardization of the great advantage later when elongated bullets
caliber improved the performance of arquebus were used, but these were not invented until the
and of the cavalry firearm, which was the 1st quarter of the 19th century
‘ ‘half-size arquebus”, known as demi-bague and It may be of inrerest to know that some
later pistol. This was at first 25” long and soldiers in the North American Continental Army
then was reduced to ca 12” in length. Rifled were equipped during the Revolutionary War
pistol was invented at the end of 16th century (1775-1783) with a sort of rifled firearm of unknown
The impr~vement in performance of European origin. These rifles were very effective
arquebus was also due to the replacement of the when using patched bullets, which were nothing
“time match” method of ignition by a firing but balls of diam slightIy smaller than that of the
mechanism known as the matchlock.(ca 1450) and rifle bore, wrapped in a small patch of greased
later by the wbeellock(ca 1520). The wheellock buckskin, linen or other suitable material. The
was a device particularly suitable for pistols patch enlarged the diam of the ball to make a
but rather weak for larger firearms. The short tight fit in the barrel. When a patched bullet was
pistols of the 17th century, known as daggs, were pushed down to its seat above the powder, the
also equipped with wheellocks patch carried with it the residue remaining from
When a larger infantry firearm, the musket, the previous firing, thus automatically cleaning
was introduced during 1520-1540 by the Spanish, the bore with eack loading. When the bullet was
it became possible to fire bullets as heavy as discharged, the patch, fitting tightly into the
2.51bs and which could stop a horse at 500 yds. grooves of the rifling, imparted the necessary
This was a formidable weapon which contributed rotation to the ball and then fell off soon after
much to successes of the Spanish Army in it left the muzzle. Despite the unusual success
conquering the Netherlands of the patched ball, the European nations
In early firearms there was no cartridge to continued to use naked balls, even in rifled
hold the chge of BkPdr or the balls. The first firearms, which came into use toward the end of
cartridge, invented ca 1560, was a paper bag for the 18th and beginning of the 19th century, The
holding BkPdt only, but a later invention(ca British created in 1800 a branch of the Army
1590) intended to have BkPdr and balls as one called the Rifle Cotps. At first the Corps was
unit. The latter cartridge was used in the Army equipped with the Baker rifle(cal ca .615) and
of Gustavus Adolphus, King of Sweden(161 1-1632). then wirh the Brunswick rifle. These rifles used
The cartridge consisted of a roll of paper which naked round balls and for this reason were not
enclosed a BkPdr chge and one or several balls. as effective as Amer rifles using tightly-fitting
The ends were either sealed or tied with a patched balls
piece of string. The cartridge was then greased The problem of producing a suitable
to waterproof it and to lubricate the bore. The military rifle missile without resorting to the
use of ready-made paper cartridges permitted patch was solved in 1823 when a special
more rapid loading and firing than when the elongated bullet was invented by the Brit Capt
loose BkPdt chge and the bullet were loaded Norton. The base of Norton’s bullet was
separately. Other improvements in muskets hollowed out in such a manner as to be expanded
included the replacement of matchlock and wheel- by the pressure developed by the powd gases
!ock by flintlock(toward the end of the 17th behind it at the instant of firing. This action
: entury) and later by the introduction of a sealed the bore against the escape of gas and
~ercussion cap(at the beginning of the 19th also forced the expanded portion of the bullet
: entuty). There was no improvement, however> into the rifling grooves sufficiently to attain the
n bullets; they were still spherical in shape, necessary rotation for accurate flight. This
llthough much smaller(l/2 OZ) than used in design was followed in 1836 by another elongated
;panish muskets(2.5 Ibs) because of the gradual bullet invented by Greener, a famous Brit
 I

B 326

gunmaker of the period. His bullet was provided mentioned that of S. Gardiner, patented in 1863
with a base cavity into which a conical plug and called “musket shell’. This expl bullet, as
was fitted. When the charge was fired the plug well as some other bullets which were used
was driven forward far enough into cavity to during the Amer Civil War, are briefly described
expand the walls of the bullet into the rifle in Ref 12
grooves which surrounded it. A different type of According to MarshaH(Ref 2a,p 176),
expandable bullet(cylindro-ogival in shape) was machine guns, used in air war, fired a proportion
designed in 1828 by the French Capt Delvigne, of explosive bullets with the object of igniting
and also by Col Thuvenin. The combination of hydrogen in the balloons of airships and
the improved bullet of Delvigne with that of gasoline in the ranks of airplanes. The expl
Thuvenin was adopted in 1846 by the French bullets used by the Germans had a percussion
Army. The next improvement in elongated cap in the nose which was detonated by the shock
bullets was the famous Minnie Bali designed by of the discharge and ignited a pellet of delay
the French Capt Minni~. This bullet, compn, which in turn fired an expl chge consisting
cylindro-ogival in shape, combined the best of KC103 , Sb2S~ & S
features of the inventions of Norton, Greener and Among the numerous variants of elongated
Delvigne. It used an iron cup in the hollow base hullers patented in the 2nd half of the 19th
which expanded to fit the rifling when the gun century, may be mentioned the one proposed in
was fired 1857 by Sir Joseph Whitworth. It was a cylin-
According to Johnson & Haven(Ref 4,pp drical bullet, the rearward portion of which was
26-9), by 1850 quite a number of elongated hexagonal. The gun had a cal .45 barrel,
bullets were known. They were, however, short hexagonal in section and with the hexagon of the
in comparison with current bullets. The most bore twisted upon itself in order to give the
efficient of older, elongated bullets was claimed huller the rotation normally imparted by other
to be the Minnie Ball. This bullet was used methods of rifling
during the Amer Civil War( 1861-65). Schematic It might also be mentioned that ca 1850
views of 60 varieties of elongated bullets used in there was patenred in the US a “self-propelled”
the middle of the 19th century are given on pp bullet intended to be fired from the so-called
26-8 of Ref 12 “Volcanic” rifle or pistol. Its cylindrical body
About 10 years before the Amer Civil War, had a hollow base which housed a small amt of
there appeared in Europe the so-called explosive MF. When struck with the firing pin, the MF
bul?ets or shell bullets. Early expl bullets, used detonared and pushed the bullet toward the
foi big game hunting, contained in a well drilled target. These bullets were not very successful
into their bodies, a chge of BkPdr which was Up to the middle of the 19th century, there
ignited by a percussion cap placed in the pose were no metallic cartridges to house a BkPdr
of the bullet. Forsyth modified the bullets by chge and a bullet. The first workable metallic
making them in two pieces which were swaged cartridge was invenred in 1846 by Houiller, a Fr
together after loading. (This would seem to be a gunsmith. The device invented by him is now
dangerous operation with rhe primer present). known as pin-fire cartridge(see under Cartridges).
Another variant was the bullet of Col Jacob of The same inventor also patented the rim-fire
Bombay ArtiHery. It was a cylindro-ogival, cartridge. The center-fire Cartridge was invented
flat-nosel caIiber .532(12 gage), 2 l/2-calibers in 1858 bY Morse(US) but it did not gain wide
-long bullet, casr with 4 broad, long lugs on its acceptance until the rarher complex design was
cylindrical surface, which fitted into as many simplified by Poret(France), Dan Baxter(England)
grooves in the bore. A cavity in the nose and most notably by Berdan(US)
carried a chge of expl which detonated on impact. With the invention of metallic cartridges,
The bullet was intended to be fired from a it became possible to use breech-loading rifles
double-barreled military 12-gage rifle. The (see under Breech-loading Weapon in this
range was up to 2000 yds and it was claimed thar Volume)
such a bullet could explode an ammo dump at a With the development, in early 1880’s! of NC
distance of 1800 yds. According to Lewis(Ref smokeless proplnts suitable for military purposes”
12), an Amer modification of this bullet(by Mead) it became evident that, due to the rather high
was used during the Amer Civil War. Among temp of burning of such proplntsY it was
other numerous inventions of expl bullets may be necessary to protect the naked bullets from the

— .
 B 327

hot gases in order to prevent melting of the lead. .22 rifle and cal .38 short Colt revolver, have
This was achieved by the invention, in the early cannelures and lubricant on the outside when the
1880’s,by Major Rubin of the Swiss Army of b@et is assembled in the cartridge case. The
~acketed bullets(a lead core cast in a case of cannelures and lubricant of “inside-lubricated”
harder metal). Asthe ballistic potential of bullets are beneath the neck of the cartridge case
smokeless proplnts is much higher than that of and$ therefore, are not visibIe in the assembled
BkPdrY weapons(and consequently bullets) of cartridge. The diameter of a lead alloy bullet is
smaller caliber, such as 6-8mm, became generally 0.003” greater than the bore diameter
predominant between grooves(see Note below)(Ref 8,p 66)
Further improvements in bullets were made Note: The caliber of a weapon is the diam of the
betw 1900 and WWL They consisted in sharpening bore(measured betw opposite lands) expressed in
the nose(pointed-nose bullets), bevelling the inches(US or Brit weapons) or in millimeters
base(boat-tailing, tapering) and replacement of (other countries’ weapons). The lands of the
steel and cupro-nickel in the jacket by gilding rifling of a weapon are the raised spiral portions
metal and allied alloys in order to eliminate formed by cutting spiral grooves(generally
excessive bore erosion and metal-fouling 0.003 or 0.004” deep) into the surface of the bore
An interesting bullet and its rifle were B)Bullets, Metal Jacketed. Naked Iead(or lead
designed in Germany before WWII by Halger. The alloy) bullets are not suitable for use in high
rifle was provided with a barrel having a bore -velocity or in automatic weapons. Only
part cone and part cylinder. The bullet was jacketed bullets should be used for these. Such
/larzged with flanges which folded back against bullets consist, in general, of a core(lead alloy)
the body when the missile entered the constricted enclosed by a gilding metal(Cu w & Zn 10%)
(cylindrical) portion of the barrel(Ref 10,p 813) jacket or a steel jacket either copper-plated or
Bullets, D ascription: The following types of covered with a thin layer of gilding metal. A
bullets are used in modern small arms: cannelure(or annular knurl) is rolled or cut into
A) Bullets, Lead. Bails made from pure lead are the jacket to provide a recess into which the
called ‘{soft” or drop balls, but usually lead is mouth of the cartridge may be crimped during
combined with tin and/or antimony(for hardness). assembly. The cannelure also serves to hold the
Such balls are called “chilled” shots. This jacket and core together more firmly. Cal .3o
alloying reduces the tendency of the lead to carbine and cal .45 pistol, revolver or sub-machine
adhere to the barrel in patches. It also helps to gun bullets do not have a csnnelure since they are
prevent the bullet from “stripping”, that is from held by their tight fit in the cartridge case. The
jumping the rifling of the weapon. The current diameter of a jacketed bullet generally should
lead bullets may be subdivided into spherical not be more than 0.001” greater than the bore
(ball, shot or pellet) and cylindrical types diam between grooves(see Note under Lead
a)Ball or Pellet 1. ead Bullets, used in shotgun Bullets)
shells and caliber .45 shot cartridges range in The body of a metal-jacketed bullet is
size betw 0.08” and 0.34’. Shotgun shells are cylindrical in shape with the nose either round,
identified as to the size of the ‘tgage” and not as in the carbine, pistol or revolver bulletst or
by caliber. The gage of a shotgun refers to the ogival(curved taper) as in all service rifle and
~umber of pure lead balls of the diameter of the machine gun bullets. The length of ogive or
>ore required to weigh 1lb. For example~ the taper for cal .3o and .50 bullets is ca 2X
;hotgun with a bore of 0.729” is a 12-gage weapon calibers. The base may be “square’ ‘(cylindrical)
>ecause 12 lead balls of that diam would weigh or’’boattailed’’( having a conical taper). A special
llb(Ref 8,pp 65-6 & 68-70) type of bullet is the ‘~wad-cutter” or “mid-range”
i)B ullets, C ylirzdrical, L cad. Lead alloy bullets V which is entirely cylindrical and has a square
cylindrical in shape with a rounded nose and front in order that it may cut the target cleanly
lat base, are currently used in cal .22 rifle ammo (Ref 8,pp 66-7). AH US bullets are required to
md in many revolver cartridges. In order to withstand storage under specified conditions
educe {‘leading” of the barrel, the bullets are and to function at the target betw -65° and
;enerally lubricated with a grease or other +170 °F(-540and 76.7°C)(Ref 7,P 73)( See Figs)
ubricating substance which is placed in two or Jacketed bullets may be subdivided into
lore cannelures or grooves cut around the bullet. the following class es: ball, ball hornet, armor
‘he ( ‘outside-lubricated” bullets, such as cal -piercing( AP ), incendiary(l ) & armo~piercing
 B 328

>PRIMER COMPOSITION _. PalMER *55EMDLY

~PAPEl< DISK (FOIL)
ANb IL
COMPOSITION

..,,.
COMPOSITION \TRACER

..
PRIMER VENT IN COMPOSITION I /ASSEMBLY
[ /CAR TP.ll)GE tiEAD

‘ -=:-1 ~ 5PRIMERvENT IN ANvIL

.4:- ,..— .

PRIMER “SQUAR:” BASE SLiJG

POCKET
EXTRACTING GROOVE

\ /
CARTRIDGE “BOAT. ~
BULLET

CANNELURE
INCENDIARY
COM~o~TION
1
‘?ti }

AT

p+-—---- ‘- - BODY
SHOULDER
L, L, ./ C6RE ‘JACKET

I HEAD
NECK OF CARTRIDGE CASE I
LI- —.- .—— CARTRIDGE CASE —— 4

Typical Bullet & Cartridgo Case Assembly

+’”-
-3
Aos
c-4b
L
F--q
o. +0.4754
%

~ .-l ..,, I wum

-’
BALL CAL = SHORT
*o’R . --”
/
LONG RIFLE,MM
@
BULLET, TRACEi CAL .+i.ml (m
US Caliber .22 Q WNeRlfu
JACKETED
6UL~
Rifle Bullets
A-GILDING METAL JACKET
B- COPPER41ATED STEEL JACKET
c-UADAmww SLw
0- IGNITER COMP051T~ Wurr, DALLo CAL. .22 LONG RiFLE
@la sMA,LaNewLaMs4
S-TRACER ~lllm US Caliber .22
US caliber .45 Ammunition
Revolver Bullets
-incendiary (API), high- explosive- incendiary(HEI), was decided to design a bullet which would
tracer(T) & armor-piercing-tracer( APT) and armor penetrate light armor and ignite inside the target.
-piercing-incendi ary-tracer(AP IT) The result of this design was the API bullet. A
a)Ball Bullets are intended for use against typical bullet contains a core of incendiary mixt
personnel and light material targets. They will and a Pb-Sb alIoy slug at the base. A hollow
usually go through an animal or man without steel cylindrical body or a clad steel container
tearing a jagged hole. The most common sizes may be inserted within the jacket and before the
used in the US are calibers .30(rifles and base slug. Cal .30 and .50 incendiary bullets Ml
carbines) and .~O(rifles and machine guns). are provided with two knurled cannelures
These bullets have long, ogived noses and flat According to Ohatt(Ref 7,p 76), the Amer
bases. There are also cal .45 revolver bullets cal ,5o API bullet used during WWII contained 15
which are roundnosed(Ref 8,p 67 & Ref 13,p 81) ~rains(ca .97g) of incendiary mixt of Ba (N03)2
b) Ball, “Hornet” Bullets are 45-grain guilding with A1/Mg alloy, placed in the nose of the
metalY fulI-jacketedJ elongated bullets authorized bullet. The mixt was ignited by heat generated on
for use in cal .22 “survival” rifle M4 and in the Impact of the bullet against a target. This caused
upper b~rel of the cal .22/.4107gage survival it to tear open the gilding metal jacket and to
rifle-shotgun M6, designed for shooting small scatter the incendiary mixt inside the rarget.
game for food putposes(Ref 13,p 81 & Ref 17,p The usual burning time of this mixt was from
38). The bullet is called “’ ‘hornet” because its 10 to 40 msecs. A more effective API bullet was
flight is accompanied by buzzing similar to that of the cal .50 M23(Ref 7,p 76)(See also Ref 8,p 67 &
a hornet and because, when shot its impact feels Ref 13,pp 81-2)
like a sting(Ref 16) e) High- Explosiue-lncendiary( HE1) Bullets contain
c )Armor-Piercirzg(AP) Bullets are intended for a chge of incendiary compn in the nose and a chge
use against armored aircraft & vehicles, light of HE in the center of the bullet(Ref 13,p 81)
concrete shelters and similar bullet-resisting f) Trace~T) and Armor-Piercing-Trace~APT)
tatgets. AP bullets consist usually of a Bullets. It is often important to be able to
gilding-metal jacket surrounding a tungsten obsetve<the entire trajectory of the projectile,
-chromium or magnesium-molybdenum stee 1 core. especially when firing at aircraft or other
The cal .30 bullet has a point filler of lead and a rapidly moving object. Machine guns on planes
gilding metal base filler between the core and the usually fire a proportion of tracer bullets, which
jacket, whereas the cal .50 bullet has only leaves a trail of smoke and sparks easily seen
lead-antimony aHoy(Pb 90 & Sb 10Z) filler. The by day or night
nose of AP bullets is a long, slender ogival type According to Marshall(Ref 2,p 564), the
to lessen retardation due to air resistance. The first modern tracers were devised in Germany in
nose is slightly flattened at the tip to provide 1909 by J .B .Semple
better penetrating power(the width of the flattened At present, there are two types of tracer
tip is called the rneplat). The base of the bulletis bullets. In the 1st type, part of the lead core at
given a slight “boattail’‘(qv) shape in order to the base end is replaced by a tracer compn, such
prevent breakage of the core during penetration as SrOz+ Sr(N03 )2+ Mg and an ignition compn Y
of the armor as well as to reduce frictional air such as Ba02+ Mg or &02 + Mg. These
resistance during flight. It is usually required that substances are pressed into the bullet at ca
AP bullets penetrate armor plate approx lfi” thick 7000 psi(4900kg/cm2) with a step punch(plunger).
without breaking them into pieces. Both types of The base(which is flat and not tapered) is
AP bullets have smooth cannelures in the jacket plugged by a fusible alloy which melts instantly
for crimping to the cartridge case(Ref 7,p 73-5; on contact with propellant gases when the chge
Ref 8,p 67 & Ref 13,p 81) is fired
d)lncendiaryfl) and Armor-Piercing incendiary The 2nd type of tracer(APT) bullet is
(API) Bullets are intended to initiate fires in aimil at ro the AP bullet except that the rear
aircraft fuel tanks, ammo and expls containers. p am-of rhe steel core is repl aced by tracer
Originally the bullets were designed on the same and Igniter compns. The length of the trace is ca
principal as the ball bullet, except that they 1200yds for cal .30 and 1800yds for cal .5o
contained a small quantity of an incendiary mixt bullets, A longer-range trace, 2500yds, used in
in the nose. Later, when AP bullets replaced some cal .50 bullets$ contains a slow-burning
ball bullets for aircraft and antiaircraft use, ir tracer mixt of Sr(N03 )2, KC104 and Mg. In all
 B 330

~. .,
,,,,
BULLET, BALL, CAL .30, M3 @uLLET, ARMOR-~ ERCINI
CAL. .30, M~
D wl-

NG CAL .S0, M2
ALUMINUM COLOR

WLLET, ARMOR-PIERCl@
CAL. .30, M14

RED
o
H I 185 IN i

BULL=, TRACERC CAL = “

m,m, *.flERcI*ItitiNmAiy-mcER, cw .50, m OR,

IGHT BLUE ORANGE
---- - jK
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3
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. ;.,,.......:,, . .. .. . ,,
. .

M ‘—-- - - ~
BULL6Tt TRACER. BULLET, TRAcERt CAL .
CAL.’ .30, M3S (TIW M2S (T72E1 )
H—INCENDIARY COMPO:
A--GILDING METAL JACKET , \ TRACER COMPOSITION
B—HARDENED ALLOY STEEL CORE — I DIM
C—GILDING METAL BASE FILLER K \TRACER COMPOSITIC
-LEAD “T” SHOT POINT FILLER ‘/BRIGHT
A- GILDING METAL JACKET G– IGNITER CMPOSITlON E.–LEAD-ANTIMONY SLUG \GILDING METAL CL#
B- STEEL CORE H –TRACER C@WOSITION F—sTEEL BODY ‘— /STEEL JACKET
C- LEAO-ANTl~ POINT FILLER I -LEAD-AWIWY SLUG G-LEAD SHOT =4 BODY FILLER M—IGNITER COMPOSITIC
D- HARDENED ALLOY STEEL CORE J -STEEL BODY
E. LEAD.ANTIMONY BASE FILLER K- GILDlffi METAL CLAD
STEEL CONTAl$iER
F-INCENDIARY MIXTURE
US Caliber .50 Bullois

.. -=’..
._~ .’ .,”.
BULLET,TRA~. CAL .50. Ml ,- .~, :
.—
‘------- ..~, ,RAC~, &UG&,;~

m% .*. ~.- ~~ ““L”--

$%#tTf]&j&’KM ““---’9us Caliba
U%caliber .30
SLUG
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B_G,LD, NGMETAL BULLET.TRAC5R, CAL .50. M1O D-LEAD.ANTIMONY
SLUG Butloi
JACRET Carbho
JACKET
C-GILDING
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E-TRACER COMFUXTION
METAL

c0MP051T10N
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Bullets F-GtLCiNGMETAL
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JKK17
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BULS.ET:
TRACER,CAL .s0, M17-

__—— __————-—————————— ._.——

1
 B 331

tracer bullets the Iight(usually red, but sometimes Anon, r ‘Platzpatrone aus Kunstoff”, Explosivst
green) is visible, day and night, only from 1961, No 4,84 16) A. B.Schilling, PicArsn, Dover,
behind and not from the sides in order not to be NJ; private communication(1961) 17)Anon,
visible to the enemy. As the light in some “Small-Arms Ammunition”, TM 9-1305-200(1961),
tracers is so strong that it can momentarily 26-38
blind the gunner in night firing, the so-called
r %ight tracer” was developed. The essential
part of such a tracer is the “dim igniter”, which Bullets, Armor-Piercing(AP), Armor-Piercing
contains Sr02, Mg & Ca resinate. It should be -lncendiary(API), Armor-Piercing-Incendiary
noted that the heat developed by some tracers is .Tracers(APIT) and Ball Bullets. See under
so great the they may also function as BULLETS
incendiaries
In order to simulate a ball of fire and to Bullets, Blank and Dummy. In blank ammo,
make the enemy think he is under fire from much which is used for simuIated fire in maneuvers
larger caliber weapons than small arms, the std and in firing salutes & signals, the bullet is
cal .50 Ml tracer btillet is modified by replacing replaced by a wadding(such as paper) sealed in
the usual igniter and tracer compns by a large the mouth of the cartridge case contg a small
amt of igniter compn alone(Sr02+ Mg). Although chge of proplnt(such as EC powder). In dummy
such compns burn for only 600yds, the int ens it y ammo~ which is used in practice for loading
of light is about 3 times the usual intensity and weapons and to simulate firing, a bullet(metallic,
is visible in all directions(Ref 2a$p 198; Ref wooden or plastic) is inserted in the cartridge
7,pp 77-8; Ref 8,P 68 & Ref 13,pp 81-2) case contg no primer and no proplnt
g)Armor-Piercing-Incendiary-TracerfAPIT) Refs: l)Ohart(1946), 65 & 80 2) Anon,
Bullets are similar to armor-piercing incendiary “Ammunition General”, TM 9-1900(1956),
(API) bullets, but in addition have a tracer compn 82 3)Merriam-Webster’s( 1961), 230
in the base end of the bullet(Ref s,p 68 & Ref
13,p 81) Bullets, Dumdum were either soft-nosed bullets
Illustrations of typical US caliber .30 and or standard bullets with vertical cuts made in
.50 bullets are included their points so that they expanded upon hitting
R efs: l)W.W.Greener, “The Gun and Its a target. When such bullets entered a body, the
Development”, Cassell, Potteq Galpin & Co, expansion usu#y resulted in fatal injuries due
London(1881), 109-13,116-18,147,152-3,170,176, to the shattering of bones and tearing huge
180 & 188-91 2)Marshall 2, (1917), 564 2a) gaps in vital organs. These bullets were named
Marshall 3(1932), 176 & 198 3)Hayes(1938), for the Dumdum Arsenal, near Calcutta, India,
656-62 4)M.M.Johnson & C.T.Haven, where the British manufd them during the Boer
‘ ‘Ammunition”, Morrow & CO, NY(1943), 21-3 War(1899-1902). Although prohibited by the
5) J. R.Newman, “The Tools of War”, Second Hague Conference for use in warfare,
Doubleday, Doran & CO, NY(1943) 6)Anon, dumdums have occasionally been used during
‘ ‘Ammunition Inspection Guide”, TM 9-1904 the 20th century by some nations
( 1944), 185,195-6,203,210-11 & 217 7)Ohart Re/s: 1)’ ‘The Modern Encyclopedia”, W.H.Wise &
(1946), 73-8 8) Anon, “Small Arms Ammunition”, Co, NY(1947), 404 2)EncyclBritannica 7(1952),
TM 9-1990(1947), 65-8,80,84,86,92,107 & 119-20 729 3)Merriam-Webster’s( 1961), 700
9)EncyclBritannica 4(1952), 372 10)Ibid 20
(1952), 802-13(under Small Arms) 1 l)Anon> Bullet Sensitivity Test. See under BULLET
‘ ‘Fundamentals of Small Arms”, TM 9-2205(1952), TESTS
32-4 12)B.R.Lewis, Ordn 38, 947-9( 1954xExpl
bullets ‘used during Amer Civil War) 12a) J.F.C. Bullets, Explosive. See under BULLETS,
Fuller, “A Military History of the Western World”, Historical
Funk & Wagnalls, NY, v 2(1955), 49, Footnote 1
12b)W.Y.Carman, “A, History of Firearms”, Bullets, Frangible. The caliber .3o frangible,
StMartin’s Press, NY(1955), 89-156& 165-79 13) ball bullet M22 used for outdoor firing practice,
Anon, r ‘Ammunition General”, TM 9-1900(1956), consists of a 50/50 blend of lead and bakelite.
73-83 14)H.C.Logan, “The Cartridges”, The cartridge is of brass, bottlenecked in
Stackpole Co, Harrisburg, Pa( 1959), 183-6 15) shape. The ‘bullet disintegrates on contact
 B 332

with the target without injuring personnel which are usually thin-walled) or explosives
Ref: Anon, “Sma117Arms Ammunition”, TM which are packed in regulation containers are
9-1305-200(1961), 46-7 safe against the effect of small arms fire, In the
methods described below expls are subjected to a
Bullets, High-Explosive-Incendiary. See under combination of impact and friction produced
BULLETS when bullets hit them and then penetrate
A)US Bullet Impact Method for Testing Explosives
Bullets, High-pressure Test of. See under In this method, also called Pipe Nipple Bomb
CARTRIDGE, AMMUNITION Test, a sample of the expl to be tested is loaded
into a pipe nipple 3“ Iong$ 2“ nominal diam and
Bullets, Incendiary. See under BULLETS with 1/8” wall thickness. The nipple is cut
from standard black iron pipe and is threaded at
Bullet Splash. It is the dispersion of finely both ends to receive std 2“ pipe caps. For press
divided or melted metal produced by a bullet loading, the nipple without caps is loaded with
upon impact with armor plate or other hard ca oo51b of expl at the desired pressure; the
objects threads are cleaned and vaselined and the caps
Ref: Glossary of 0rd(1959), 50 assembled to the nipple to be held by at least
two threads at each end. For cast-loading, one
Bullets, Shell. Same as Bullets, Explosive end of the nipple is closed with a cap and the
molten sample(ca 0.51b) is poured into the
Bullets, Spotter-Tracer. The caliber .50 assembly. After the expl has cooled it is faced
spotter-tracer bullet has a gilding metal jacket off flush with the end of the nipple. The thre,ads
contg an incendiary chge in an Al-alloy container> are then cleaned and vaselined before the 2nd
and a tracer and igniter compn in a steel cap is screwed on the nipple to be held by at
container. The ctge case is of brass. Upon least two threads. The resulting loaded assembly
contact with a target, the bullet will produce a is called a bomb. Once the caps are assembled,
flash and a light puff of smoke. It is used in cal no attempt should be made to remove them and if
.50 rifle for spotting the target for the gunner there is any doubt about the contents of the bomb
before firing the 106-mm rifle, M40 or its method of loading, the bomb should be
Ref: Anon, “Small-Arms Ammunition”, TM destroyed
9-1305-200(1961), 60 The correctly-assembled bomb is placed in
an upright position on a stand which is located
Bullets, Tracer. See under BULLETS 90ft(ca 27.5m) from the muzzle of a cd .30 std
infantry rifle rigidly supported in a barricade.
BULLET TESTS, Because a modern bullet is an Five or more bombs are usually prepd for each
integral part of a cartridge, its examination for expl to be tested. Each of these bombs is
defects is conducted at the same time as the subjected to the impact of one bullet(usually
cartridge is examined. The following tests Ball, M2) fired in such a way that it passes
concern only bullets: through the bomb entirely below the upper cap
I) Bullet Fit(Jump) Test for Caliber .45 and above the bottom cap and as close to the
Ammunition. When cal .45 ammo is fired in a longitudinal axis as possible. The observed
revolver, recoil of the weapon tends to cause the results of the bullet impact may be described as
bullets in the unfired cartridges to move forward follo~s: a)Unaffected- no visible or audible
and, if the bullets are not held tightly in indication of action b)Smoke(visible fumes or
postion in the cartridges cases, they can jam vapors) or burning(visible flash, flame or glowing)
the cylinder and prevent it from revolving. The and c)Detonation, which can be partial(weak
test described in Ref 9,p 5 has the purpose of sound, smoke and/or flame; cracking of the bomb
determining whether or not the ammo for cal .45 or bursting into very large pieces leaving a
jams the mechanism of a revolver when fired large amt of unconsumed expl) and complete(loud
ll)Bullet Impact Test; Bullet Frictional Impact report, smoke and/or flame; complete bursting
Test; Bullet Sensitivity Test or Rifle Bullet of the bomb into a large number of small
Test(CaIled Shooting Test in Ref 1). The fragments, leaving no unconsumed expl)(Ref 5,p
purpose of this test is to .iet.st ,o;.15 t} bvllat 4; Ref 10,P. 31; Ref 15,P 49 & Ref 16,99 8-9)
extent various ammunition(especially bombs, The table given on pages i3335-38 lists bullet
 B 333

sensitivity values detd in the US for several by a steel plate or block. Finally, a metal disc
expls, most of which are suitable for military (of varying thickness) through which the bullet
purposes must pass is placed against the expl at the
The possibility of using cal .5o bullets front end of the bomb. This assembled container
for some expls which cannot be detonated or are is called a “disc bomb”. The bullet is fired
difficult to detonate with cal .30 bullets was lengthwise into the chge of expl
investigated during WWII at the Explosive A modification of this disc bomb involves
Research Laboratory, Bruceton, Pa. Results of use of a pipe nipple(as in the US Method A)
this investigation were reported in Ref4,pp 14-16 capped at one end only and covered with a steel
B)US Bullet Impact MetbodModification). disc over the other end of”the expl chge, The
According to Stein &Pollack(Ref 16,p l), the bullet is fired thru the disc, lengthwise, into
nipple bomb described above is not very satis- the chge with the capped end backed by a steel
factory because the bullet strikes the curved block
surface thereby introducing undesirable variables Test results showed that even cast TNT
which are inherent in a curved surface. To could be detond fairly consistently with a
eliminate this problem a new bomb was designed 220-grain bullet but less consistently with
which presents a f I at surface perpendicular to 172-grain SP(soft point) or 166-grain AP bullets.
the line of fire. This new bombx however, retains Flaked or grained TNT and cast pentolite could
a major deficiency of impact testing in that the also be detonated consistently(Ref 5a,pp 2-4)
explosive reaction is only described D)Bullet Test, French Method. This test is more
qualitatively in terms of detonation(complete or rigid than the US methods described above and
incomplete)~ burning ~ smoke, or unaffected. The is more or less quantitative. The test was
new bomb consists of a metal cylinder 3“ long developed and used at the Laboratoire de la
and 2“ diam. The ends of the bomb are closed Commission des Substances Explosives and also
by two fiat plates, 2. 5“ wide by 4“ long, which used in other labs. The test is conducted with
are attached to each other by means of two bolts an expl placed in a square box made by attaching
and nuts. For cast loading, one of the plates a wooden frame$ 80 x 80mm & 60mm high$ with
is welded prior to loading the cylinder while the 12-15mm wall thickness, to a square steel
other pIate is boIted after loading. For press plate 10mm thick. A charge of HE to be tested
I’bading, both plates are attached by means of 2 is cast or compressed in the box to the exact
bolts and nuts to the ends of the cylinder after height of 30mm. It takes betw 300 & 500g of
it has been loaded with ca 5 lb of expl. Each expl(depending on the desired density) to fill
bomb is then placed on a stand in such a manner the box to that height. The open end of the box
that the pIate of one end faces the muzzle of the is then covered with a screen made of thin wires.
rifle. The results are reported as in Method A After a similar screen has been placed in front
This test may afso be conducted by using of the muzzle of the riflex the box is set on one
cover plates of various thicknesses and by side with the screen toward the rifle and
vatylng the length of the explosive column. For located at exactly 25m from the other screen and
example, increasing the cover plate thickness parallel to it. After con netting electrically each
from 0.250” to 0.375” increases the percentage of screen to a chronograph(such as LeBoulang< or
detonations from 94 to 100 for 50/50 Pentolite, Sadir<arpentier), the rifle is fired using a
from 31 to 50 for Composition B and from 60 to 90 truncated brass bullet(balle D en laiton), cal 8mm
for 67/33 BaratoL When 80/20 Triton ai was use~ and weighing 8.lg. The bullet, after passing
however, the % decreased from 50 to O. An through the screen and 30-mm layer of explosive,
increase in percentage of detonations was strikes the steel plate but does not pierce it, thus
observed also for some expls when the length remaining inside the box. For bullet velocities
of the expl column was increased from 1“ to 2“ ranging from 210 to 840m/sec the Lebel Rifle,
and then to 3“ Model 1884, is used, whereas for higher velocities
C)Disc Method of Hercules Powder Company. In more modern weapons are required. Propellant
this test procedure, the expl is loaded into steel known as “poudre BFPi “ is used in these
pipe bombs I“ or 2“ in diam and of varying wall tests. Variations in velocities are achieved by
thickness from 1/8 to 1/4”. Instead of the usual changing the wt of proplnt in the cartridge case.
screw cap, a base plate can be welded to the In these the highest velocity at which no
bomb, or omitted, and the assembly can be backed detonations take place and the lowest velocity
 B 334

required to cause complete detonation are detd. (Ref 17)

In the case of weak expl~, such as DNT or some III)Bullet penetration Test(also called Bullet
mining expls, the size of the box used is Impact Test). This test is conducted to determine
100 x 100mm and 60mm high, but the test is the the ability of armor-piercing bullets to penetrate
same(Refs 12,13 & 14) or perforate when fired at armor plate. This is
usually done by firing at 100yds against an
FRENCH BULLET
TEST armor plate target properly mounted and supported.
The angle of impact should be 85 to 90 degrees
—
between the longitudinal axis of the bullet and
the plate(Ref 11 ,p 42)
sive lV)Bullet Pull Test. The purpose of this test
is to determine if a bullet is properly held in a
cartridge case. The test is conducted in an
Plate ), .. . apparatus which registers the force required to
L/\. “,
pull the bullet from the cartridge case. Following
are the required bullet pull fore es for cliff erent
calibers of ammo: a)Cal .22 long rifle- not less
than 281bs b)Cal .30 rifle and carbine- not less
than 451bs c)Cal .45 revolver- not less than
%ooclen Frame 401bs and d)Cal .50 rifle and machine gun- not
12-15 mm Thick less than 2001bs(Ref 1 l,p 44)
V)Bullet Stripping Test. In this test it is
The table on page B339 gives results of these determined whether or not the jackets of bullets
tests for some expls
strip from the core during flight(Ref 1 l,p 42)
E)Bullet Impact Test Described by Colver. In VI)Bullet Tracer Test. In this test, tracer ammo
the test briefly outlined by Colver(Ref l,p 647), is fired from a machine gun and the number of
the explosive is packed in cases which are shots failing to trace the required distance is
arranged in a longitudinal row at various recorded. Also are recorded the number of
distances from a rifle. The minimum distance aL muzzle bursts, blinds, or other erratic function-
which an expl detonates is noted as are the ings(Ref ll,p 42)
number of shots fired$ the thickness of the layer Refs: l)Colver(1918), 647 2)W.R.Tomlinson,
penetrated and the velocity of the bullet. The Jr, ‘ ‘Development of Explosive of High Brisance”,
shorter the distance and the larger the number of PATR 1170( 1942)(Cyclotol contg RDX 30 & TNT
required shots to cause detonat~on~ the less 70% was found to be insensitive to rifle bullet
sensitive is the expl. Loosely-packed expls are impact, whereas CyCloTol contg RDX 60 & TNT
usually more sensitive than those packed in 40% with 1% wax added burned completely in
cartridge form one of five trials) 3)W, R. Tomlinson, Jr,
F)US Bullet Impact Test for Bombs. In this ‘ ‘Special Tests of Sensitivity of TNT”, PATR
test cal .30 AP, cal .50 AP, tracer and ball ammo 1217( 1942)( Sensitivity to rifle bullet impact of
as well as 20mm AP & HEI shells are fired at liquid TNT’s is greater than that of solid
service muzzle velocity and at a range of 100 to material provided the liquid is confined to such
300yds, against loaded but unfuzed bombs. A a degree that it cannot move under impact due
minimum of 10 single shots, if possible, are to its incompressibility, and thereby dissipate
fired at each bomb and an undamage surface is the energy of impact translational y) 4)D.P.
turned toward the rifle for each shot. In addition, McDougall et al, “Studies of the Setisitivity of
a sustained burst is fired at one location on the Explosives to Bullet Impact”, OSRD 31 49(1943)
bomb body. At least the cal .50 AP & tracer and (The testing of ordinary HE’s with cal .50 Ball,
20mm AP & HEI are to be fired; use of other M2 ammo is briefly discussed and compared with
bullets is optional. Observation should be made analogous tests made with cal .30 Ball, M2 ammo.
for burning, -low- or high-order detonation, flash Next, the testing methods found appropriate for
intensity smoke density and smoke color. When aluminized expls are discussed and finally> tests
a fire results from an impact, the observations for typical demolition expls to the impact of
should include the time of burning, color of incendiary and tracer bullets are described) 5)
flame, evidence of scorching and color of smoke W. R. Tomlinson, Jr, ‘*Compilation of Rifle Bullet
 Table Ill
Rifle Bullet Impact Sensitivity of Explosives Tested in 1. or 2.inch Pipe Nipples with Caliber .30, Ball, M2,
Unless Otherwise Stated
Diam of Method Density Ij;mber % % Detonated
Explosive Nipple of of ;naf- Smoked
inches Loading Loading Trials fected PartiaI omplete
;umed
Amatol-80/20(AN 80 & TNT 20%) 2 Cast 1.50 5 100 -,
1 Pressed 1.60 10 100
Amatol 50/50 (AN 50 & TNT 50%) Cast 1.55 5 100
Ammonium Nitrate(AN) : Pressed 1.2 10 100
Ammonium P erchi orate No information
Ammonium Picrate(AP)(Explosive D) 2 Pressed 1.50 10 70 30
1 Pressed 1.2 5 100
* Pressed 10 70 ;0
Baratol-67/33(Ba nitrate 67 & 2 Cast ;.55
TNT 33%) * ? ? :: %
Baronal(Ba nitrate 50, TNT 35 & 1 Cast 2.32 9 50
Al 15%)
Black Powder(K nitrate 75, No information
Charcoaf 15 & sulfur 10%) I I
Blasting Gelawt See tabl’e under item D(French Method)
Borotorpex(RDX 46, TNT 44 & 2 Cast ? 10 — 50 —
B powder 10%)
Composition A, Aluminized(RDX 1 Pressed 1.6 11 91 9
73, Al powder 18 & wax 9%)
Composition A-3(RDX 91 & 2 Pressed 1.59 5 — —
beeswax 9%) Pressed 1.59
Composition B(RDX 60 & TNT 40 ; Cast 1.68 2: : 7
with 1 % wax added) 2 Cast 1.68 20 44 0

Composition C(Brit PE-2)(RDX 2 Hand- 1.58 5 100

88.3 & non-expl oily ~lastlciz- tsmp ed
er, contg 0.6% lecithin, 11.77.)
Composition C-2(RDX 78.7, TNT 2 Hand- 1.52 5 80 —f
5.0, DNT 12.0, MNT 2.7, NC0.6& solvent 1.0%) tamped
Composition C-3(RDX 77, tetryl 3, 2 Hand- 1.57 —
5 60
TNT 4, DNT 10, T5&Nc l%) * tamped ? 10 80 ;0
Composition C-4 PRDX 91, polyiso- 2 Hand- 1.59 5 80 20
butylene 2.1, motor oil 1.6 & tamp ed
di(2-etliylhexyl) sebacate 5. ~%1 * ?? ? 10 40
60
Cordite” 2 Pellets ? 3 ;00
Cyclofive(RDX 53 & Fivonite 47%) 1 Cast ? 20 ;0 ;0 5
i Cvclonite or RDX See Cycl trimethylenetrinitramine
Cjclotetrsmethy lenetetranitram- No information
ine(HMX)(beta) I
Cyclotol-75/25(RDX 75 & TNT 25%) 2 Cast 1.71 10 40 30
? ;:
I
L
Cyclotol-70/30(RDX 70 & TNT 30%)
—.. . . —.
;
2
~asr
?
-.— . . .. ..
1.71
?
. .. ..—
i:
10
40
10
——. . .. . .—— -- ?0 —
TO

*Loaded in bomb No 2 as described in Ref 16

 Table Ill
Rifle Bullet Impact Sensitivity of Explosives Tested in 1. or 2.inch Pipe Nipples with Caliber .30, Ball, M2,
Unless Otherwise Stated
( f
Diarn of Method Density Number % % Detonated
Nip ple of of %
, of Un af- Smoked
Explosive inches Loading Loading Trials or GGi- ;ompl ete
fected
Burned
Cyclotol-60/40(RDX 60 & TNT 40%) Cast 1.68 20
Cyclotrimethyl enetrinitramine i 25 55 5
Pressed 1.65
(cyclonite or RDX) 1 ,, 1,6 100
; — ;0 40
Cyclotrimeth lenetrinitros- See table under item D(French Method)
amine(R Salt 1’
DBX(RDX 21, AN 21, TNT 40 & Al 18%) 1 Cast 1.65 11 55 45 — —
Dentex(RDX 48, DNT 34 & Al powd 2 Cast ? 10 30 70 — —
18% with 0.7% w ax added)

Diethanoldinitram ine Dinitrate 2 Cast ? 7 57.1 14.3 28.6

(DINA) l
Diethyleneglycol Dinitrate 1 Liq 1’.38 3 100
(DEGDN)
Dinitrodi(~-nitro xyeth y l)- 1 Cast ? 5 40 60
oxamide(NENO) I
Dipentaerythritol Hex a- No information
nitrate(DP EHN)
DNT ‘ See table under item D(French Method)
EDDN See Ethylenediamine Dinitrate
EDNA or Haleite See Ethylenedinitramine
Ednafive(EDNA 50 & Fivonite 50%) Cast ? 25 60 4
Ednatol-55/45(EDNA 55 & TNT 45%) ; 36
tasJ I 1.62 15 93 7
EMMET See Trimethylolpropane Trlrritrate
Eth lenediamine Dinitrate 5 100
(EDhN)
Ethvlenedinitram ine(EDNA or 2 Pressed 1.6o 20 60 —
Hal~ite) 1 IS “ ; — 40 —
Explosive D ~;; Ammonium Picrate
Fivonite(Tetram ethvlolcvclo- Cast ? 33 51.5 45.5 3.0
)en tanone ‘Tetranit; ate) “
Gianidine Picrate(GuP) 1 Pressed 1.0 I 10 100
u-k See Conf Ref 20,p 388
Ha~eite or EDNA See Eth ylenedinitramine
HBX-1 and HBX-3 See Conf Ref 20,pp 382 & 385
Hexanitrodipheny lam ine(HNDPh A) No information
HMX See Cyclotetramethy lenetetranitramine
HTA-3 See Conf Ref 20,p 402
iiannitol Hexanitrate
Medium Velocity Dynamite(MVD)
No information
2 Machine 1.1 —
(RDX 75, TNT 15, starch 5, SAENO 10
oil 4 & Vistanex Oil Gel 1$%) I
-ramped
I I 10 90 10

Metriol Trinitrate
Minol-2(AN 40, TNT 40 & Al 20%)
No inforrn~tion
2 Cast I 1.68 19 100 —
 Table Ill
Rifle Bullet Impact Sensitivity of Explosives Tested in 1. or 2. inch Pipe Nipples with Caliber .30, Ball, M2,

Unless Otherwise Stated

r
Diarrr of Method Den si ty Number % % % Detonated
Explosive Nipple of of of Un af- Smoked .
inches Loading Loading Trials fected ~ ~urned Partial Comple tc
Minol-2(AN 40, TN”~ 40&AI 20%) ** cast
MVD 1.68 10 — ! —
See Medium VeIocity Dynamite 100 –
NENA Same as @-Nitroxyethylnitramine I
NENO See Dinitrodi(~-ni troxyethyl)oxamide
NitroceHulose(NC) No ~formation 1
Nitroglycerlne{NG) Liq 1.6 —
Nitroglycol(NGc) or Glycol s l– 100
No information-
Dinitrate.
Nitroguanidine( NGu) 2 pressed 1.50 5 100 — —
1 Pressed 1.0 10 100 — —
Nitrostarch(NS) No infoqn a+on
itrostarch Demolition Explosive 2 Han d- 0.92
Y NS( 12. 50%N) 49, Ba nitrate 40, tamped 10 10 90
MNN 7, p-MNA 3 & oil 1%)
~-Nitroxyethylnitramine( NENA) No information I
0ctol,75/25(HMX 75 & TNT 25%) See Conf Ref 20,p 429
PB-RDX See Plastic Bonded RDX
PE-2(Plastic Explosive-2 )(Bri t) See Composition C
Pentaerythritol Tetranitrate 2 Pressed 1.70
(PETN) 1 Pressed 1.6 100
2 i ;0 50
Pentaerythritol Trinitrate(PETRIN) See Conf Ref 20,P 440
Pentofive(PETN 50 & Fivonite 50%) 1“ Cast ?
Pentolite-50/50 (PETN 50 & TNT >0%)
Pentonal(PETN 47, TNT 33 & Al 20%)
PETN
PETRIN
; I Cast
Cast
1.66
?
See Pentaerythritol Tetetranitrate
See Pentaerythritol Trinitrate
7
;t?
;
15 70
70
5
100
72
10

Picramide See TrinitroaniIine

Picratol-52/48(PA 52 & TNT 48%) 2 cast 1.63 10
? 60 40 – –
? 50 — —
Picratol, Ammonium( Ammonium ; Cast ?
Picrate 53 & TNT 47%) *** ;: ;: 10 —
Pic ric kcid(PA) or 2,4,6 Cast ?
.Trinitrophenol 11 36.4 18.2 36.4 9.0
; Pressed 1.64 40 60 –
PIPE(PETN 81 & Gulf Crown 2 Hand-
E Oil 19%) 1.37 ; 100 —
tamped
Plastic Bonded RD~(PB-RDX) S>e Conf Ref 20.,p 434
PL X( Nitromethane 95 & Ethyl- 2 Liq
snediamine 57.) 1.12 5 100
PTX-l(RDX 30, Tetryl 50 & TNT 20%) 2 Cast
PTX-2(RDX 41-44, PETN 26-28 1.64 5 60 20 20
2 Cast 1.70 5 45
k TNT 33-28%) 30 25
?VA-.4(RDX 90-9.2, polyvinyl- 2 Cast
~cetate 8-6 & DBuPh 2%) 1.60 5 20 60 - 20

*Loaded in bomb No 2 described in Ref 16 **Loaded in 100-Ib GP Bomb AN-M30(Ref 7a, P 19) *** U~ing cal .50 Ball, M2
 Table Ill
Rifle Bullet Impact Sensitivity of Explosives Tested in 1. or 2.inch Pipe Nipples with Caliber .30, Ball, M2,
Unless Otherwise Stated
4 8
Dimn of Method Density }~m ber % % Detonated
$n af- Smoked
Explosive hl~h:l: of of or P titi’a i CompI ete
Loading Loading Trials fected Burned
UPE(RDX85 & Crown E Oil 15%) 2 Hand- 1.37 10 100 —
tamped
{-Salt See Cyclotrimethylenetrinitrosamine

;evranite See Table in $r;;sD~renc h M:~d)

;hellite(PA 59 & 2,4-DNPh 50%) 1 100
Cast ? ?0 100
;ilico-hiinol AN 40 TNT 40 & : Cast ? 2 100
lilicon pow i er 20%’) I
retramethylolcy clopentanone See Fivonite
retrani trat e
Tetryl( 2 ,4,6- Trinitrophenyl Pressed 1.6 30 20 10
-N-methyln itramine) ; “ 1.71 : % 54 13
* “ ? 10 70 :
r etrytol-75/25(Tetryl 75 & 2 Cast 1.6o 5 72 ?8 :
TNT 25%)
Tetrytol-6>/35( Tetryl 65 & 2 Cast 1.60 5 90 — 10 –
TNT 35%)
TNT See Trini tro tolunee
Tol ami,te See table under item 1)(French M~thod)
Torpex-2(RDX 42, TNT 40 & M 18%) 2 cast 1.81 5 80 20
? ? 10 — — 100
; Flake 1.3 4 iOo
rorpex, German(RDX 20,5, TNT 57.7 2 Cast 10 ?0 75 ?5 -
k ~ ‘21.8%)
Tridit<Ammonium Pi crate 80 & No inforination
DNPh 20%)
Trinetbylolp ropane Trinicrate 2 ? ? 8 — 50 } 50
(EMMET)
Trimoni te(PA 88-9o & MNN 12-10%) 1.60 5 100 — —
,2 Cast
Trinitroaniline( TNA) or Picramide ,No information
Trim troph enol See Picric Acid
Trinltrotoluene( TNT) Cast 1.56 25 96 1
; C.ast 1.56 45 71 :2 7 :
Trip ent aerythritol Octo- See Conf Ref 20,p 465
ni trate(TP EON)

Tritonal(TNT 80 & Al 20%) Cast 1.72 25 60 –

; ? ? $ 40 -
* ? ? ?:
? 10 E — 2: :
Veltex See*&nf I ef ;O,p 470

*Loaded in Bomb No 2 described in Ref 16 **Loaded in 100-lb GP Bomb AN-M30(Ref 7a,p 19)
 Table IV Rifle Bullet Impact Test by. the French Method
Bullet Velocity, m/see
Density I Maximum for Minimum for
Explosive glcm No Detonation Complete
Detonation
PETN 0.7 257 290
RDX 1.0 274 327
Tetryl 1.0 280 330
PA 1.0 370 393
PA, cast 1.65 1087 No deton
R-Sal t 0.6 505 515
TI’JT(Grade T) 0.85 675 714
TNT, cast 1.6 1042 No deton
TNT(Grade D) 1.15 704 740
NGu,needles 0.6 781 793
lVVN,~wdered 0.9 833 No deton
1.0 96o 1040
(incomplete)
DNT 1.0 1040 No deton
PETN/Psraffin-97. 5/2.5 0.75 355 396
“ “ -95/5 0.70 471 515
“ ,, -90/10 0.65 657 666
“ ,, -85/15 0.70 819 833
“ “ -82.5/17.50 0.70 1000 ~;6deton
PETN/MNN-95/5 0.70 390
RDX/Paraffi:;9~7 j/2. 5 0.90 714 724
“ 0.85 769 793
, 0.95 1063 1110
RDX/Be;swa;9~~1~/7 5 0.95 833’ 847
RDX/MNN - “ “ 431 463
PETN/TNT-50/50 i:; 310 335
,, “ H (cast) 1.65 943 1042
?ETN/TNT-20/80 1.05 335 385
,, “ “ (cast) 1.65 1063 No deton
lDX/TNT-60/40 1.3 390 400
“ “ ,, (cast) 1.7 980 1000
lDx/TNT-50/50 396 400
“ with 1% wax added ;:: 616 641
lDX/TNT-62/38 with 1% 1.0 543 547
wax added
ret l/TNT-70 /30(cast) 1.55 1042 No deton
AN7mT-50/50 1.0 471 500
“ (cast) 1.30 1087 No deton
4N/;~T-60/40 1.05 543 561
4N/Sawdust-87/13 0.8 1111 No deton
4N/Al powder-82/18 0.9 537 793
4N/RDX-52/48 1.0 322 357
4N/PETN-33.3/66.7 0.85 301 316
4N/DNN-87. 5/12.5 0.9 550 575
B1asting Gelatin-95. 5/7.5 .280 357
~ETN/TNT/Al-40/40 /20 ~:;5 266 297
n (cast) 670 806
R;X/TN;/Al~40/40 /20 1:0 349 360
909 925
iN/;NT/Al-4:%/20 ;:$5 337 364
n (cast) 1.2 781 833
;NT~A1-85Jl 5(clst) 1087 No deton
Comp C( Brit PE-2)(tamped) ;:;5 1021 No deton
~omp c-2( t amped) 1.7 1021 No deton
rolsmite(NG 27.0, NC 1.0, 1.5 316 337
DNT 9.5, cellulose 1.5 &
AN 61.0%)
Sevranite No l(PETN 48, 1.55 333 347
Amm perchlorate 31, Al 3
k plasticizer 18%)
DNT/NaC103-28/72 301 337
TNT/N aC103-38/62 ::; 254 294

NO te; All expls were pressed except those marked “cast” or “tamped”
 B 340

Impact Test Data of MiIitary Explosives”, reported for military expls, such as PA, ~T,
Chemical Rept, Pic Arsenal, Dover, NJ(1943); Tetryl, PETN & RDX; for mixts, such as
published as section 2 in OSRD 3156(1944) 5a) PETN/TNTY RDX/TNT and for mining expls,
R. W. Lawrence & J.E.Meyers, “Sensitiveness of such as Dynamite-gommey Tolamite, Sevranite$
High Explosives to Rifle Bullets’‘,_Experiment ExplQsif O, Explosif N) 15)AnonY “Military
Station, Hercules Power Co, Wilmington, Del Explosives”, TM 9-1910(1955), 49( Sensitivity to
(1944); published as seen 1 in OSRD 3156(1944) Rifle Bullet Impact ; 322-3, table 1) 16)S.
6)D.I.Hedrick, ‘ “The Sensitivity to projectile Stein & M. E. Pollack, “Development of an
Impact of Explosives in Various Containers”, Improved Rifle Bullet Impact-Sensitivity Test”,
Rept NO 19-43(1943), Naval proving Ground, PATR 2247(1956) 17) Anon, t ‘Ordnance proof
Dahlgren, Va ; published as seen 4in OSRD Manual”, OPM 10-86. Aberdeen PG, Md(1957),p 2
3156( 1944)( The thickness and material of the (Bullet impact tests for bombs) 18)H.Will &
container play an important part in detg the action G. Silvestro, “Development of Method for
of impact. Thick cases offer considerable Determining the Sensitivity of Explosives to
protection to the charge from cal .30 ball and Bullet Impact”, Instrumentation Rept No TR
20mm HE projectiles. Against cal .30 AP 681-58, PicArsn, Dover, NJ(1958) 19)W.R.
bullets, TNT was the safest expl, but it gave a Tomlinson, Jr, “Properties of Explosives of
low-order deton upon impact by cal .50 AP Military Interest”, PATR 1740, Revision 1(1958)
bullet) 7)E.H.Eyster et al, “The Effect of by O.E .Sheffield 20)0.E .Sheffield, “Properties
Small Calloer Projectiles on HE Loaded Bombs of Explosives of Military Interest”, P ATR
and SheIls”, Rept of Aberdeen PG, published as 1740, Supplement No l(1958)(Conf) 21)W.H.
seen 5 in OSRD 3156(1944)(Rifle bullet tests Rinkenbach, Allentown, Pa; private communica-
were conducted wirh various bombs loaded with tion(1961)
TNT or other HE’s. In testing a 4000-lb LC
M56bomb loaded with 50/50 Amatol, it was Bull Goose or Goose. Popular name for a US
found that it could be detonated by impact of Air Force delta-wing air-breather, diversionary
cal .50 bullets fired from a machine gun at a missile designed by the Fairchild Engine &
range of 300 yds; the same may sometimes be Airplane Corp. The Goose is launched, together
true with cal .30 AP bullets, also fired from a with real mis’siles or manned bombers to act
machine gun. Results of testing smaller bombs, as a’ decoy to attract enemy defense system
such as 25- and 100-lb, loaded with TNT, devices(such as radar) away from the real
60/40-Sodatol, 80/20-Amatol, 60/40-TNN/TNT, missiles or bombers. It is powered by a
65/35-TNT/GuN and Tridite, are also reported) Fairchild J-83 turbojet engine which produces
7a) R. A.Connor et al, OSRD Rept 5406(1945), 15 & ca 2000-pound thrust. The Ramo-Woolridge Corp
17.19 (Rifle bullet test values for HBX, Minol-2, provides the electronic countermeasures equipment
Torpex-2, TNT & Tritonal) 8)E.H.Eyster & carried in the Bull Goose
W. H. Rogers ‘tThe Sensitivity of Explosives to Refs: I)Glossary of 0rd(1959), 50 2)C. E. Davis,
Bullet Impact”, OSRD 5745( 1945)( The rept deals t ‘The Book of Missiles”, Dodd, Mead & Co,
with ‘ ‘ordinary” cast HE’s, with < ‘ordinary” NY(1959), 52
pressed HE’s, with some aluminized expls and
with some liquid expls. A German method of Bullpup Missile(X-ASM-N-7). A US Navy air-to
testing is briefly described on p 11) 9) Anon, -surface missile manufd by the Glenn L. Martin
“ ‘Ordnance Proof Manual”, OPM 7-24, Aberdeen Co(now Martin Marietta Corp), having a canard
PG, Md(1945), p 5 10) Ohart(1946), 31 1 l) Anon, configuration and using an Aerojet General
‘ ‘Small Arms Ammunition”, TM 9-1990(1947), solid-propellant rocket. It” was designed to be
42-4( Bullet Stripping Test, Bullet Penetration launched by attack aircraft from any position
Test, Bullet Fit Test and Bullet Pull Test are outside the effective range of enemy high volume
briefly described) 12)E.Butlot, MAF 23, 185 ground fire and to provide sufficient accuracy to
( 1949)(Detonation of ordinary expls by impact destroy small targets without excessive sorties
of solid projectiles launched at great velocities) and expenditure of large quantities of bombs
13)L.M6dard & (?)Cessat, MAF 23, 195-203(1949) and rockets, It carries a conventional warhead
(Comparison of behavior of various expls to which is contact fuzed. A proximity fuze can
impact of bullets) 14)A.LeRoux, MP 33, also be used in it. The advanced versions of
283-321 (1951 )( Sensitivity to bullet impact Bullpup are Bulldog and White Lance
 B 341

Re/s: l)G.Merrill, “Dictionary of Guided Bunsen, Robert W. von(1811-1899), A Ger

Missiles and Space Flight”, Van Nostrand, chemist noted for gasometric and photometric
NY(1959), 104 and illustration facing p 59 researches and for various inventions, such as
2)Glossary of Ord(1959), 50 3)C.E.Davis, “The burner, valve, cell, clamp & funnel audiometer.
Book of Missiles”, Dodd, Mead & CO, NY(1959), The first theory of the burning process of black
30 powder was estabiIished by him and
simultaneously by a Russian chemist$ L.
Bullseye Powder. The following double-base Shishkoff. Bunsen lost the sight of his right
propellant: NC(13.25%N) 60.0, NG 3!9.5 & DPhA eye due to the expln of cacodyl cyanide, which
0.5%, in the form of circular flakes, diam he discovered together with other derivs of
0.035” and thickness 0.005”, was subjected cacodyl
during WWII at PicArsn to 65.5°. Surveillance Re/s: l) H. Goldschmidt, ZAngewChem 24,
and to 120° & 134-5° Heat Tests. The results of 2137-40(191 l)(Recollections of Robert Wilhelm
these tests, reported by Rinkenbach(Ref 1), Bunsen) la)C.Cranz, “Lehrbuch der Ballistik”
showed that this proplnt was of satisfactory 2, -Springer, Berlin( 1926) 2)F .J .Moore, “A
stability. According to Westheimer et al(Ref 2), History of Chemistry ~, McGraw-Hill, NY( 1939),
Bullseye Powder is manufd by Hercules Powder 264-71 3)Hackh’s(1944), 147 4)M.E.
Co, Wilmington, Del. One of their Bullseye Serebryakoff, %terior Ballistics”, Moscow( 1949),
proplnts manufd during WWII was in the form of Abbreviated English translation for the US Navy
7/8” sticks, which consisted of NC(13.257%N) by Dr V. A. Nekrassoff, Catholic University of
58.~NG 40.0, EtCentr 1.0 & DPhA 0.29% with America, Washington, DC(1954), 25 5)E .Farber,
some carbon black added(Ref 3) Edit, “Great Chemists”, Interscience, NY(1961),
Refs: l)W.H.Rinkenbach, PATR 1359(1943), 573-81
p 2 & table II 2)F.H.Westheimer et al, OSRD
Rept 4758(1945), p 10 3)G.D.Clift, private Bunsen Valve. A simple device which allows the
communication 1962) air or vapor to escape from a closed container
(such as a flask) but does not allow air to
Bullseye Powder(Modern). No info at our disposal re-enter. It may be prepd in the following manner:
Insert a glass rod, Smm diam and ca 6“
Bullseye Modified. Same as JPT Propellant long, into a piece of rubber tubing(perferably of
pure gum) of 3mm bore, 2“ long and 1.25mm wall.
Bumblebee. A series of surface-to-air missiles Cut, by means of a razor blade, a slot in the
sponsored by the US Navy and developed by tubing ca 3/8” long and at an angle of 15-200 to
various contractors under the technical direction the axis. Remove the glass rod and slip one end
of Johns Hopkins University, Baltimore, Md of the tubing onto a piece of glass tubing 2“ long
Re/: DictyGuidedMissiles( 1959), 104 and ca 5mm OD. This is inserted in a rubber
Note: A series of confidential reports were stopper fitting the flask or other container. Close
issued on this subject by Johns Hopkins the other end of the rubber tubing with a short
University, Baltimore, Md, Contract NOrd- 7386 piece of glass rod or a small stopper. Seal all
joints with shellac and allow to dry
BuMines or BurMines. Abbrn for the Bureau of To test the valve, remove the glass tube
Mines(US) from the rubber stopper of the flask and note if
the slot allows passage of air when some
Bumper. The code name of a high-altitude pressure is applied. Then connect the tube to a
rocket involving the V-2/WAC-Corporal first water pump and see if it creates a vacuum
and second stages R e/s: l)Clift & Fedoroff 3(1943), Chap II,P 13
2)Hackh’s( 1944), 888
Bumper Missile is a two-stage rocket missile
R ef: DictyGuidedMissiles( 1959), 104 BuOrd. Abbrn for the Bureau of Ordnance(US
Navy)
Bu-NENA. Designation for N-(2-Nitroxyethyl)
-butylnitramine described here as [ 1-(N Buramine. A butyl urea-formaldehyde resin
-Butylnitramino) -ethan-2-ol ] Nitrate under manuf during WWII by the Sharples Solvent Co.
But ylaminoethanol and Derivatives It was employed in a butanol soln(65% concn) as
 B 342

a binder in some molded composite proplnts. Bureau of Mines(BuMin or BurMines), US Dept of

Eg: 218 B(Propellant): Buramine 5.1, Amm Interior, Washington 25, DC, Created in 1910 as
picrate 46.7, Na nitrate 46.7, i’‘Santi cizer 8** parr of the Dept of Interior, transferred in 1925
(plasticizer manufd by Monsanto Chemical Co) to Dept of Commerce and retransferred to Dept of
1.5 & Ca stearate 0.4p Interior in 1934. The purpose of the BuMin is to
R ef: ‘ ‘Summary Technical Report of Division 8, design, promore methods for conservation and
NDRC” VO1 1(1946), 96 development of mineral resources and to assure
healthful working conditions in the mineral
Bureau of Aeronautics(BuAer), US Navy, industries. It also conducts research in
established in 1921 and abolished in 1959. Its technology of fuels ~ explosives, minerals,
functions were transferred(with those of helium, etc. Its research on expls(mainly mining
Bureau of Ordnance) to the Bureau of Naval expls) is conducted at Pittsburg and at Bruceton,
Weapons(qv), effective July 1, 1960 Pa. Results of researches are published as
Bulletins, Technical Papers or Reports of
Bureau of Explosives(BuExpl) or more fully, Investigation. For more information on activities
Bureau for the Sa{e Transportation o/ Exfiloszve~ of BurMines, see “United States Government
and other Dangerous Articles. The BuExpl was Organization Manual 1961-62”, USGovtPtgOff,
established by the American Railway Association Washington 25, DC, Revised as of June 1961,PP
in 1906, three years before the organization of 247-8 & 661
ICC(Interstate Commerce Commission). In 1934,
the AmRyAsso created through consolidation Bureau of Naval Weapons(BuWeap), US Navy,
with other organizations~ the ‘Association of Washington ’25, DC, formerly Bureau of Ordnance,
American Railroads, Bureau of Explosives”. The is responsible for the research, development
BuExpl makes inspections, conducts investigations design, testing, operating standards, manufacture,
and confers with manufactures and shippers of procurement, fitting-out, storage, distribution,
explosives and other dangerous materials, with issue$ maintenance, alteration! repair, overhaul,
the view of detg what regulations will afford the material effectiveness disposition and salvage
highest degree of safety(within reasonable of all naval weapons, ammunition, explosives,
1imits) in packing and prepg these materials for propellants, pyrotechnics, war chemicals,
shipping. The BurExpl thus became expert in aircraft and other equipment. The Bureau is also
the handling of expls and has thereby established charged with operation of weapons, expls &
its shipping regulations. Its inspectors are proplnts plants, laboratories, torpedo stations,
stationed throughout the US to observe ~ ammo depots, ordnance test stations and other
investigate and report upon shipping methods. naval establishments. For a more complete
The common carriers utilize the services of the description of its functions, see “United States
BuExpl in enforcing. regulations as well as in Government organization Manual 1961-62”,
assisting shippers(Refs 1 & 2) USGovtPtgOff, Washington 25, DC, Revised as of
The BuExpl publishes various pamphlets, June 1, 1961,p 178
as well as shipping regulations, known as
‘ ‘Interstate Commerce Commission Regulations” Bureau of Ordnance(BuOrd), USNaVy, established
(See Refs 3 & 4). These publications may be in 1842 and abolished in 1959. Its functions were
obtained by writing to T.C.George, Agent, 63 transferred(with those of Bureau of Aeronautics)
Vesey St, New York 7, NY to the Bureau of Naval Weapons, effective
Refs: l)US Chief of Ordnance, “Safety and not later than July 1, 1960
Storage Manual for Explosives and Ammunition”,
00 Form No 5994, Washington, DC( 1928), seen 8 Bureau of Standards or National Bureau of
2)M.Newton, “The Bureau of Explosives”, Standards(NBS), Washington 25, DC. It was
ChemInd, Dec 1944,PP 928-30 3)Sax(1957),secn 11 established in 1901 as a part of the Treasury
4)Agent T.C.George’s Tariff No 13, “Interstate Dept and was transferred in 1903 to the Dept of
Commerce Commision Regulations for Transporting Commerce and Labor. The fundamental purpose
Explosives and Other Dangerous Articles by of the Bureau is to provide national leadership
Land and Water in Rail Freight Service and by in the development and use of accurate & uniform
Motor Vehicle(Highway) and Water”, New York 7, techniques of physical measurements, It conducts
NY(Sept 15, 1960) (Supplements 1 & 2 added) fundamental research in physics, chemistry,
 B 343

mathematics and engineering in order to lay f~rms of oxidation. At atm temp oxidation of a
the ground work for new standards. It also combustible material generally occurs, if at all,
tests, calibrates and certifies various measuring only very slowly> and usually with little outward
devices, such as thermometers, barometers, etc. manifestation. When, however, the temp is
The Bureau at present publishes: The Journal of raised, as for example by the application of
the National Bureau of Standards and Technical some external source of heat$ the process
News Bulletin. It formerly published: Bulletin becomes greatly accelerated and, when the
of the Bureau of Standards(1904- 1919), w-hich was “ignition point” is reached, heat will be developed
replaced by Scientific Papers(now discontinued). at a rate greater than that at which it can be
There were also published Technological dissipated and flame will eqsue. Thus, when a
Papers, which also have been discontinued. For lighted match is applied to coal gas issuing
more info on NBS see “United States Government from a jet, the temp is raised to the ignition
organization Manual 1961-62”, USGovtPtgOff, point of the gas. Flame then appears and is
Washington 25, DC, Revised as of June 1961 ,pp maintained at the jet, Similarly$ when coal is
309-11 & 668 heaped on a fire, its volatile constituents,
liberated by heat, mix with surrounding air and
Burette Calibration. See under Calibration of after ignition give rise to flame; the residual
Laboratory Glassware coke consists largely of carbon which becomes
incandescent and burns without flame
Burn Cuts. A term used in blasting operations. Combustion must be distinguished from
See Blaster’s Hdb(1952), 260-2 deflagration, explosion and detonation(See also
Combustion, Catalytic and Combustion, Spontaneous)
Burned Shots. Same as Blown-out Shots(qv) Re/s.’ l)EncyclBritannica 6(1952), 98 2)
Merriam-Websters( 1961), 300
Burner. A device for obtaining a flame by the
combustion of solids, liquids or gases. In Burning Area, Required. In rocket technology,
rocketry~ it means a fuel-injection nozzle in the it is the area of solid-propellant material that is
combustion chamber of a jet engine or the made available for combustion to satisfy the
combustion chamber itself performance requirements at a particular moment
Refs: 1 )Hackh’s(1944), 144 2)DictGuidedMissles in the firing interval, One of the means of
( 1959)., 104 varying the burning area is the selection of the
proper configuration of a proplnt grain
Burner Plate. The term occasionally used by Re/: Rocket Encycl(1959), 384
Brit rocket technologists for “injector”
Re/: RocketEncycl(1959), 60 Burning and Burning Characteristics of Explosives,
Including Experimental Procedures. Although
Burning and Combustion(Definition). Burning in the literature on the subject of burning of expls
common usage is defined! in Ref 2, as a is very conflicting~ it is possible to draw the
combustion is which material is consumed by following general conclusions:
fire resulting from interaction of the material a)Small charges of explosives ~ including all low
with atmospheric oxygen at high temperature and expls and many secondary HE ‘s(such as TNT,
accompanied by flame and sometimes sound dynamites and blasting gelatin) can be made to
According to Ref 1, the term combustion burn quietly if they are unconfined
implies the process of burning and in the popular b)Burning of secondary HE ‘s(especially PETN,
mind is generallY associated with the production RDX, and HMX) can lead, often after long delay,
of flame. So far as @rrestial conditions are to detonation especially if large quantities of
concerned, combustion is due to the combination materials are involved or if they are under strong
of a combustible substance with oxygen and the confinement
consequent evolution of heat. The appearance c)Primary expls, according to some investigators 7
of flame is due to the oxidation of gases or such as Muraour(Ref 18) and Griffiths & Groocock
vapors at a very rapid rate so that high temps are (Ref 24), detonate instead of burn; but some
obtained, the molecules involved thereby becoming other investigators, such as Belyaev & Belyaeva
very radiant. Scientifically, the term combustion (Refs 10 & 13), claimed that primary expls, with
has a broader meaning and is extended to other the exception of LSt, can bum in air when they
 1

B 344

are highly compressed in the fo~ of cylinders 14, 523-46 (1941k& CA 36, 4339( 1942)( Discussion
A comprehensive review by Andreev on on burning of nitroglycol) 7)A. F. Belyaev,
burning of expls is being published in several DoklAkadN 28, 714-17 (1940)(in Engl) & CA 35,
numbers of Explosivstoffe(Ref 25) 5317( 1941)(A mathematical discussion showing
Experimental procedures for detn of that under certain conditions where orderly
burning rates and other characteristics of expls burning of expls in parallel layers is disturbed
are discussed in Refs 2,10,15,20,20 a,22,23 & 25 by violent boiling of molten expl at the surface,
This section was reviewed by Dr J .P. or by presence of pores which permit the flame to
Picard penetrate into the mass, stable burning is not
Re/s: l)C .E .Munroe & J .E .Tiffany, “Physical possible and there may be transition from
Testing of Explosives” ~ BurMines Bulletin 346, deflagration to detonation) 8) K. K. Andreev,
USGovtPtgOff, Washington, DC(1931), 30-1 [Detn DoklAkadN 29, 469-73(1940) & CA 35, 6456(1941)
of rate of burning of low expls~ such as black [Investigation of ‘burning of secondary HE’s
powder(blasting) in the Bichel pressure gage under increasing pressure was conducted in
after certain modifications were introduced by heavy iron tubes sealed at the bottom and
A. B. Coates & J. E. Crawshaw] 2) A. W. Baker, close’d at the top by a lead or steel disc. The
ExplosivesEngr 17, 115-17(1939) & CA 33, 566 pressure in the tube was controlled by varying
( 1939)( Apparatus for detn of burning rates of the thickness of the disc. When ignited, gelatinous
pellets of BkPdr consists of a steel tube closed expls(such as gelatin dynamites or blasting
at one end. A c-innon crusher gage is placed in gelatin) burned without detonation, while
the closed section of the tube and a pellet of pulverulent expls detonated when the increase
BkPdr is then placed next to the crusher gage. in the rate of burning produced a critical pressure
The cartridge is fired electrically and the length in the combustion front. For example, RDX &
of the gage is then measured and the amount of PETN detonated under the confinement of a
crushing is compared with that caused by a lead disc 2 .5mm thick which corresponded to
standard powder. The length that the crusher is 65kg/cm2 pressure while TNT, PA or tetryl
shortened is proportional to the force of the blow required confinement of a steel disc which
which> in turn, is proportional to the speed of corresponded to a pressure of 500-700 kg/cm2 ]
burning of the powder) 3) H. Mouraout, RevGenSci 9)K.K.Andreev et al, KhimReferatZh 1940Y No
44, 567-71( 1933)(A resum~ and elaboration of 10/ll,p 120 & CA 37, 1872( 1943)( Experiments of
theories of burning and detonation of HE’s and A. et al have shown that in general the rate of
proplnts discussed in earlier papers of Muraour burning of expls tends to increase with decrease
et al) 4)M.Patry, SS 32, 148-51,175-9,199-205, in the diam of the tube, or decrease in the
225-31,264-9, 295-300 & 335-40(1937); Ibid 33, density. For some expls, such as Nitroglycol,
6-10,33 -7,65-9,92-6 & 156-9( 1958) (Burning and 62% Gelatin Dynamite or Blasting Gelatin, the
Detonation of various expls, such as Azides, diam of chge does not seem to influence the
Fulminates, Cheddites, Dynamites, PETN, PA, rate of burning) 10)A.F.Belyaev & A.E.
RDX, Tetryl, TNT and Tricycloacetoneperoxide) Bel yaeva, DoklAkadN 33, 41-4(in Ger)( 1941) &
5)A.F.Belyaev, ActaPhysicochim 8, 763-8(1938) CA 37, 2183(1943) [Pellets of MF compressed at
(in English); ZhFizKhim 12, 93-9(1938)& CA 1750kg/cm2 decompd without detonation at atm
33, 8992( 1939)(As most secondary HE’s are and lower pressures in reactions which were
appreciably volatile near their ignition temps$ s elf-support ing(’ ‘burning’ ‘). The rate of ‘ ‘burning”
the evapn may absorb most of the energy of MF at 760mm was found to be 1.5-2.Ocm/see,
liberated at the burning face. B. therefore believes which is higher than that for secondary HE’s
that their burning takes place in the gas phase (0.05 ro O.lcm/’sec). When the pressure was
and that the penetration of burning from the gas decreased to 100mm, the rate decreased and
phase into the condensed phase may lead to the flame became longer but weaker. At 8mm and 2
immediate development of detonation. Since to 3min, no flame could be seen and the pellets
most proplnts are not volatile they burn without seemed to melt. B & B came to the conclusion
detonation. This therory does not hold for some that the burning of MF pellets at atm pressure is
primary expls- their burning goes to detonation a two-step process.$ consisting of : a)the
although they are not volatile at the temp of distintergration of part of the substances with
burning) 6)A.F.Belyaev, ZhFizKhim 14, 1009-25 formation of very small particles and b)the
(1940) & CA 35, 4207(1941); ActaPhysicochim complete decompn of these particles> close to
 B 345

the surface of the pellet] 1 l) Ya.B.Zel ‘dovich, 1st test, known as combustion en goutiere
ZhEkspTeoretFiz 12, 498-524(1942) & CA 37, (burning in a trough), a sample of loose expl is
4249( 1943 )( Discussion on stationary and non placed and leveled to fill a horizontal semi
-stationary burning of expls and proplnts. This -cylindrical trough, 10 or 20mm in diam and
includes rate of burning and transition from 2 .Om long, made of sheet steel, 2-mm thick. The
burning to detonation) . 12) K. K. Andreev, length of the trough was marked at 0,0.5,1 .0,1.5 &
ZhFizKhim 20, 467-92(1946) & CA 41, 283-5 2.Om. After igniting the expl(at the end marked
(1947 )(Discussion on burning of various liq & O) by a Bunsen burner(or candle or alcohol
solid expls at low pressures) 13) A. F. Belyaev & burner), the time required for the flame from the
A. E. Belyaeva, DoklAkadN 52, 503-9( 1946)(in burning explosive to travel the distances 0.5,
Engl & Rus); complete translation OTS: 60-41, 1.Om. etc is detd and the average rate of burning
512: JPRS: 4080(1960) may be obtained from in cm/sec is calcd. In the 2nd test, called
OTS/USDC; CA 41, 4309-10(1947) [Highly combustion en tas conique(burning in a conical
compressed cylinders of some primary expls pile), a sample of loose expl(lkg) is placed on
burn at the rates: 1.55 cm/sec for MF at d 3.80: dry, hard ground(or on a cement floor) in the
0.65 for TATNB at d 1.70; 0.95 for Tricycloace- form of a cone with the smallest possible base,
toneperoxide at d 1.22; 2.15 for DADNPh at d After measuring the diam of the base and the
1.45 and 1.50 for K picrate at d 1.83. LSt height of the cone, the expl is ignited at the
exploded instead of burning but its mixt with 60% base by means of a torch and the time required to
of talcum burned at the rate of 14. 5cm/sec and consume the pile by burning is observed. These
the mixt of MF 60 & talcum 40z burned at the two tests are used in the Laboratoire de la
rate of 0.55cm/sec. At low press(10-22mm Hg) Commission des Substances Explosives, France]
the character of the burning varied with the expl 20a) A. M. Gurvich &, Yu.Kh.Shuvalov,
except that TATNB still burned with a stable ‘ ‘Termodinamicheskiye Izsledovaniya Metodom
flame] 14)K.K.Andreev, DoklAkadN S3, 233-6 Vztyva i Raschety Protsessov Goreniya”
( 1946) & CA 41, 6722( 1947)(Influence of cubic (Thermodynamic Investigation by the Explosion
density on the burning of expls) 15)H.Muraout & Method and Calculations of Burning Processes),
A, Michel-L~vy, MAF 21, 263-70(1947) & CA 44, IzdatelMoscovUniv( 1955) 21)A.Douillet, Mp
8659( 1950)(Spectral study of the phenomena of 37, 167-96( 1955)( Exptl study of the laws of
burning and detonation of expls) 16)G.N. burning of BkPdrs at atm pressure and belcw)
Abramovich & L.A .Vulis, DoklAkadN 55, 107-10 22)K.K.Andreev, “Termicheskoye Razolzheniye i
( 1947) & CA 41, 6723( 1947)(Mechanism of Goreniye Vzrychatykh Veshchestv’ ‘(Thermal
propagation of detonation and of burning in Decomposition and Burning of Explosives),
expls) 17)A.F .Belyriev & A.E .Bel yaeva, Gosenergoizdat, Moscow(1957)(a book in Russian)
DoklAkadN 56, 491-4(1947)& CA 44, 8109(1950) 22) F. P. Bowden et al, “Combustion and Explosion
[The rate of burning of some primary expls of Crystals” ~ in 6th Symposium on Combustion,
under increased pressure obeys the same law as Reinhold, NY(1957),PP 609-12(9 refs) 23)N.
was applied by Andreev(Ref 8) to secondary Grif fiths & J .M.Groocock, ARDE(Great Britian)
expls. If v is the linear rate of burning, Repts(MX)5/59 & (MX)6/59,March 1959, t’Burning
p- pressure and A & b constants, then of Solid Explosives to Detonation. Development
v= A+bp] 18)H.Muraour, “Poudres et Explosifs” of Photographic Techniques” 23a)C.Campbell &
Presses Universitaires de France, Paris(1947), G.Weingarten, PicArsnMonograph M43(1959),” A
20-2(MY in collaboration with J. Basset, verified Thermoanalytical Study of the Ignition and
that all high expls including blasting gelatin Combustion Reactions of Black Powder” 24)N.
bur excluding primary expls can burn without Griffiths & J .M.Groocock, JCS 1960, 4154-62 &
detonation when ignited by a flame whether in Explosivst 1961, 276 [Expls other than initiating
the open or in a closed vessel at pressures up compds usually bum when ignited, but burning of
to 10000kg/cm2) 19)H.C .Grimshaw, “SIOW secondary HE’s(such as PETN, RDX or HMX) can
Burning of Permitted Explosives as a Possible lead to detonation often after a long delay,
Cause of Hangfires or Delayed Explosions”, particularly if large quantities of materials are
Ministry of Fuel and Power, Safety in Mines involved or if they are confined. Some tests
Research Establishment, Research Rept No conducted by these investigators showed that
34, 3-29( 19jl)(Brit) 20) L. M~dard, MP 33, narrow columns of heavily confined secondary
329-30(195 1) [TWO tests are described. In the HE’s achieved detonation after a relatively gentle
 I

B 346

thermal ignition ] 25)K.K.Andreev, Explosivst The conditions of burning propellants in a

1960,54 -61,102-11,167-77,275-84; Ibid 1961, closed vessel and in a gun are not the same
198-207, 233-40, 257-64; Ibid 1962,35-9,47-52, In a closed vessel, the gas produced on
136-48,158-68,177 -86,203-12(to be continued) burning, streams out along the normals to the
(Thermal decomposition and burning of expls) proplnt surface and, if the chge is not concentrated
near one end of the vessel, the gas velocities
Burning and Burning Characteristics of Propellants parallel to the burning surfaces are negligible.
for Artillery Weapons and Small Arms, When a This means that if a proplnt burning in a closed
charge of colloidal propellant consisting of a vessel is without perforations(such as cordite)$
number of geometrically similar pieces(called there is no erosion of the grains, but if a proplnt
grains) is brought in contact with an igniter is perforated(as in US single- and multiperforated
system capable of heating nearly simultaneously grains) there is erosion in channels but not on
the surfaces of all grains to at least 1700F, the the outside surfaces of grains
propellant starts to burn and evolve hot gases. In burning of proplnts in a gun, there is
The heat of these gases brings successive movement of the gas stream from breech to muzzle
layers of the grains to the temp of ignition and parallel to the grains of proplnt with a relative
this maintains continuous burning. If a proplnt is velocity of some hundreds of feet per second.
carefully prepd to achieve homogeneity, there Although the distributi~n of gas velocity along
is no reason why it should burn preferentially in the bore at a given time is not known accurately
any particular direction. It is, therefore, safe it is usually assumed that this velocity is
to assume that the surface of each grain recedes proportional to the distance from the breech.
parallel to itself as burning proceeds. This Generally, it may be assumed that the proplnt
phenomenon of burning in parallel layers was burning in a gun behaves at first as in a closed
first observed in 1839 and is now known in vessel and then shows a rate of burning greater
internal ballistics as Piombert’s Law. Some than found in a closed vessel at the same
confirmation that this law is obeyed(at least pressure. Near the end of burning the erosion
approx) in practice is obtained by firing prophts effect may decrease, since the gas velocity
in guns with barrels too short to permit complete along the proplnt increases but slowly at this
burning of grains while the projectile is still in time, while the proplnt velocity rises rapidly;
the bore. The pieces of unburnt proplnt are then hence the relative velocity can therefore fall.
thrown from the gun and are caught in water to Further, the very last stages of burning are
arrest burning. If the recovered grains are marked by a decreasing burning surface. The
generally found upon examination to be of the resultants of these effects is obviously complex
same shape as the original grains but smaller in (Refs 4,24,25 & 33)(See also Burning, Erosive
size, it proves the validity of piomberr’s Law of Propellants)
Piombert’s Law does not hold if the grains Propellants intended for use in rifles or
are perforated, because here the stream of hot guns are required to possess the following
gases, passing through the channels, causes characteristics:
their surfaces(internal) to burn faster than the a)The burning shall be rather slow in order not
external surfaces of the same grains. The to produce an excessive pressure of gases in the
increase in rate of burning is observed for any bore on firing. At the same time, that pressure
surface of a grain if it is subjected to the action shall be sufficiently high to impart to the
of a stream of hot gases moving with an projectile the desired muzzle velocity. This
appreciable relative velocity, parallel(or nearly pressure shall not drop below a certain level
parallel) to the surface. The effect of causing while the projectile travels toward the muzzle
an increase in rate of burning due to the b)Burning shall be such that no excessive
movement of hot gases along the surfaces or erosion of metal bore is produced and that the
through the channels of the grains is known as ballistics shall be regular, ie, when different
erosion of propellants or erosive burning. This projectiles of the same shape, diameter, length
effect is more pronounced with cool proplnts(such and weight are fired by equal wts of propints,
as those contg NGu) and depends at any time on practically identical muzzle velocities shall be
the density of the proplnt, the size of obtained
perforations and the relative velocity of hot gases c)Burning of completely gelatinized proplnts
moving paralleI to the surfaces of grains shall be uniform from the surface and shall obey
 B 347

(approx) Piombert’s Law(see above )(Refs 1,4,24, area of the grain is reduced as the grain is
25 & 33) consumed
The term burning characteristics might AH perforated grains, especially
include burning rate$ burning time, burning mulriperforated ones~ burn progressively because
temperature and some other properties the burning surface of the grain increases as the
Burning rate, also called quickness or grain is consumed
speed of combustion(Verb rennungsgeschwindigkeit As to the web thickvess, the larger the
in Ger, Vitesse de combustion in Fr~ Skorost’ value, the slower is the proplnt. For single
goreniya in Rus, VeIocitk delIa combustion in -perforated grains, as most US small arms
Ital and Rapidez de la combusti~n in Span), may proplnts are, the web thickness is equal to half
be defined as the rate(in mm/see, cm/sec or the difference betw the outside diam(such as
in/see) at the surface of a proplnt grain recedes 0.049” ) and the diam of the perforation such as
when it is consumed in a combustion chamber 0.015“)
The rate of burning is dependent on the c) Porosity and surface treatment of propellants.
following: Porous grains(usually produced by insufficient
a) Composition 01 propellant. In a single-base gelatinization of NC) are faster burning than
proplnt, the higher the N content of the NC the non-porous grains. Surface treatment of proplnts,
faster-burning is the proplnt. In a double-base such as with retardants or with graphite, produces
proplnt, the higher the content of NG or of DEGDN, proplnts which burn SIOWIY at the beginning and
the faster and hotter is the proplnt. NGu is added faster after the upper layer has burnt out
to reduce, the temp and the rate of burning. d)pressure of confinement. The higher the
Non-expl ingredients, such as volatile solvents pressure the higher is the rate of burning of the
(alcohol, ether, acetone), plasticizers & proplnt provided orher conditions are equal.
stabilizers(vaselin, sym-dialkylureas, DPhA, When a proplnt starts to burn in a gun the
centralizes, acardites), flash reducers(K2S04, pressure is atmospheric and the rate of burning
KH tartrate) and coating agents(graphite), is comparatively low. Then the pressure begins
considerably reduce the rate of burning and energy to increase due to evolving gases because the
of proplnts. The same applies in. a smaller movement of the projectile toward the muzzle is
degree to the presence of moisture in proplnts. not sufficiently fast to allow release of all the
Colloidal proplnts contg an emulsion as a evolving gases. The increase of pressure in the
stabilizer are faster-burning than similar proplnts bore causes the proplnt ro burn faster than
with a solid stabilizer(such as DPhA or earlier and this causes a still higher rate of
centrality) distributed homogeneously in the increase in pressure. The pressure and the
proplnt. The rate also depends on particle size rate of burning continue to increase until certain
of the solid ingredients. This is of particular maximums are reached for both of them, The
importance in proplnts contg large amts of pressure then starts to decrease and this causes
solid ingredients) such as “cool” proplnts a decrease in the rate of burning. As soon as
contg NGu or “composite” rocket proplnts all the proplnt is consumed the projectile is
b)Size and shape of grains and web thickness. ejected from the bore.
When a proplnt is ignited at const pressure it If a NC proplnt is t ‘fast-burning’ ‘(for
bums at a uniform rate of speed in parallel example$ when NC is not sufficiently gelatinized
layers in a direcrion perpendicular to all exposed or if the grains of proplnt are too small), the
surfaces, provided the compn is uniform rapid combustion of part of the proplnt might
(Piombert’s Law). The greater the surface create such a high pressure that the remaining
exposed to combustion rhe faster is the prop!nti chge would deflagrate or even explode(Ref 35),
provided other factors, such as compn and In NC-NG proplnts expln might take place if the
confinement are the same in alI rests. The finer contenr of NG is too high
granulated(smaller grains) proplnts possess According to investigations conducted by
greater surface per unit charge(or volume) and Brunswig(Ref 6), the effect of pressure on the
therefore burn faster then proplnts with coarser rate of burning NC proplnts is not the same as
granulation(k-ger grains). The surface of large for NC-NG proplnts. On plotting the pressures
grains may be increased by flattening them as abscissa and the rates of burning as ordinatey
All solid grains, such as strips, cords, Brunswig obtained curves which showed the
cubes? etc burn depressively because the surface following: a) The rates of NC propInts at low
 1

B 34a

pressures were always very low b)As the but also the various phenomena associated with
pressure increased to the middle range, the burning of proplnts, such as erosion of proplnts,
proportional in crease in rate for NC proplnts ignition, erosion of the gun barrel> etc. A
was slightly higher than for NC-NG proplnts successful theory would provide a general
c)When the pressure began to increase to higher understanding of these phenomena and might
range$ the proportional increase became nearly indicate khe possibilities of control. Although
equal for all proplnts and the curves became a theory of burning may show small discrepancies
practically parallel to each other with the NC-NG from experimental data, it is, however, useful
curves considerably above the NC curves. In All theories of burning described up to the
all cases the higher the NG content the higher present in open literature may be divided into
was the final value for the rate of burning(see surface theories and vapor-phase theories
also Ref 13) A) Surface theories. According to these theories
Burning rates can be detd experiment ally(see burning is controlled by the rate at which energy
Burning Characteristics of Propellants, (such as heat) is transmitted from the hot
Experimental Procedures) or they can be calcd gaseous products to the surface of solid proplnts
approx by one of the equations listed below (Ref 24,pp 43’7 and Ref 25,pp 24-5). These
Early gun ballisticians who burned proplnts theories have been suggested by L~tang(Ref 2),
at pressures of the order of 30000 to 50000 psi Schweikert(Ref 3), Muraour(Refs 5,7,8,9 & 11),
were satisfied to express pressure effects of Yamaga(Ref 10) and Crow & Grimshaw(Ref 12).
burning artillery propellants by the equation: A review of Muraour’s work was given by
V.bp$ where v is the rate of burrring at a given Schmidt(Ref 15). All surface theories lead to the
temp~ p- pressure and b a constant conclusion that the rate of burning depends upon
According to Marshall 1 (Ref 1), Vieille the gas temp near the solid and that the rate is
proposed in 1884, in collaboration with Sarrau, proportional to pressure(except at high pressures
the following experimental equation: where the effect of the finite size of the gas
v=cpx(Eq I)Y where c & x are constants molecules becomes significant)(Ref 24,p 47)
As these equations did not hold for Brit B )Vapor-phase theories. According to these
Cordite, Mansell & Petavel proposed the theories the reaction of burning precedes in the
following linear equation: v=ao+ ap(Eq 2), where layer of gas just outside of the solid(Ref 24,pp
p is pressure, a. is the rate of burning at atm 47-9 and Ref 25Yp 25-6). These theories have
pressure and a is acceleration of the rate of been suggested by Boys & Corner(Refs 22 & 23),
burning per unit pressure. After a certain Belyaev(Ref 18) and some other investigators
pressure has been produced, the value a increases Saenger(Ref 26) proposed a hypothesis
rapidly to become constant until all of the which considers the process of burning of a
proplnt has been consumed. This constant, solid proplnt to occur in three layers. In the 1st
known as burning velocity index is of major layer, a partial decompn takes place betw the
importance in the burning of artillery proplnts starting temp T, and the ignition themp T2. In
(Ref 29a,pp 229-30) the 2nd Iayer(separation layer) the proplnt
Eq 2 is written in Ref 29a as: R.a + bp molecules melt$ boil and vaporize and in the 3rd
Eq 1, known as Vieille’s Law or layer(reaction layer) the substance burns to
C‘exponential formula” ~ is used now by many C02 & H20 at temp T3. By considering that the
investigators(esp eci aIly in rock etry),while Eq 2 heat absorbed betw T, & T2 and betw T2 & T3 is
has been preferred by Muraour and his school converted to chemiluminescene of the combustion
The present accumulated data for various gases, a formula is developed for the stationary
types of colloidal proplnts permits one to det rate of burning of the proplnt. For more info on
approximately their rate of burning if composition the subject” consult the original paper
and/or some properties such as calorimetric The same investigator(Ref 26a) gave for
value or temp of expln) are known. This burning of NC-NG proplnt the following expressiorr:
knowledge, is purely empirical and does not V= I/y(E, ~+ Eza ) where I is the intensity of
explain the process of burning as would a good radiation producedj y - density, E - heat evolved
theory of burning. The real value of a theory in going from ambient temp to flas~temp, and
lies in its physical and chemical picture of the E ~ ~- heat evolved in going from flash temp to
process. If a theory is close to the truth it helps combustion temp
one to understand not only the burning itself Increase in the initial temp of a proplrrt
 B 349

causes an increase in the burning. rate. Decrease 19)K.K.Andreev, DoklAkadN 29, 469-73(1940)
in burning rate because of decreage in initial temp (Burning under increased pressure) 20)C.M.
results in decreased pressures; ~d because of Dickey, E. I.duPcmt Memorandum Rept 31(1943)
difficulty in achieving satisfactory ignition, (Detn of burning characteristics of proplnts)
there frequently results an increase in the 20a)0.K.Rice, OSRD 5224(PBL 30767(1945)
variation of projectile velocit,~. The effects in (Theory of burning of double-base rocket proplnts)
changes in the initial temp ~ less pronounced 2 l) H. Muraour, “Pouders et Explosifs”, presses
in artillery ammo than in r@kets(Ref 29a,p 231) Universitaires de France, Paris(1747),22-34
Burning characteritiics of std US gun, 22)s.F.Boys & J .Corner, PrRoySoc 197A, 90-106
proplnts at temps 21° to -52°C is discussed by (1949) 23) J.Corner, PrRoySoc 198A, 388-405
Shulman et al(Ref 36) ( 1949) 24)Corner, Ballistics(1950), 35-49 & 400
A brief mathematical discussion of effect 25a)R,I.Wilfong et al, JPhCollChem 54, 863-72
of temp on burning rate is given under Burning ( 1950 )(Hypothesis for burning of proplnts) 25)
and Burning Characteristics of Propellants for SACMS, Ballistics(1951), 23-6,38,40 & 52 26)E.
Rockets Saenger, ZNaturforsch 5a, 467-9(1950) & CA 45,
This section was reviewed by Dr. ].P. 2209-10( 195 1)(A hypothesis for burning of proplnt~
Picard 27) H.Muraour & G. Aunis, MAF 25, 117-65(1951)
R efs: I) Marshall 1(1917), 310 2)G. L~tang, (Study of the laws of burning of colloidal proplnts)
CR 168, 1313-15(1919) & MAF 1, 955-99(1922) 27a) E.Saenger, ZPhysikChem 197, 265-76(1951) &
(The phenomena produced on burning of proplnt CA 47, 320(1953 )( Theory of burning of proplnts)
in a closed vessel) 3) G. Schweikert~ { ‘Innere 28)S.Travers, MAF 25, 167-73(195 l)(Remarks on
Ballistic”, Leipzig(1923) 4) C. Cranz, “Lehrbuch the above paper of Muraour & Aunis) 29)W.
der Ballistic”, Springer, Berlin, VOI 2(1926), 1120 Guttmann, Sprengtechnik 1952, 47-52(Theory of
5)H.Muraour, BullFr 39, 11 15-19(1926) proplnt burning) 29) H. Muraour & G. Aunis, MP
(Mathematical discussion of the law governing 35, 286-301( 1953)(Laws of burning of colloidaI
burning of smokeless proplnts ) 6) Brunswig, proplntso Historical review of work done in
Propellants(1926), 218 7)H.Muraour, BullFr France between 1884 and 1953. Included are
41, 1451(1927) 8)H.Muraour, CR 187, 289-90 & 50 refs) 29a)A. O. Pallingston & M. Weinstein,
374-5(1928); ZPhysikChem 139A, 163-8(1928) PATR 2005( 1954) (Method of calcn of intericr
(Laws governing burning of colloidal proplnts) ballistics properties of proplnts from closed
9)H.Muraour & G. Aunis, CR 190, 485-8(1930) & bomb tests) 29b)Anon, “Military explosives,
BuIIFr 47, 261-73( 1930)(Laws governing burning TM 9-1910(1955), 40 & 229-31 (Burning rates of
of colloidal proplnts) 10)N.Yagama, SS 25, 60-2 proplnts) 30)P. Tavernier, MAF 30, 117-66(1956)
( 1930)( Rates of burning of smokeless proplnts) (Burning characteristics calcns for a proplnt
ll)H.Muraour & G. Aunis, CR 192, 227-9(1931) with seven perforations) 3 l)W.F. Wallace,
(Theory of burning of proplnts in a closed vessel) PATR 2488(1958)(New formulas for rapid calcn of
12) A. D.Crow & W .E .Grimshaw, PhilTrRoySoc linear burning rates of solid proplnts) 32)J.
230A, 387-411(1931) & MAF 12, 177(1933 )(Laws Delacarte et al, MP 41, 223-65 (1959 )( Contribution
of burning of coIloidal proplnts) 13)MarshaH 3 to study of rates of burning and other props of
(1932), 91 14)F.R.W.Hunt & G. H. Hinds, composite proplnts) 33) J, Taylor, “Solid
PrRoySoc 138A, 696-707 (1932 )( Rates of burning Propellant and Exothermic Compositions”,
of colloidal proplnts) 15)A.Schmidt, SS 27, Interscience, NY(1959), 55-6 34) C. Napoly, Mp
1-5. 45-8 & 82-5( 1932)( The laws of b~ning of 42, 229-46(1960)(4 refs)(Relations between
solid expls, particularly proplnts, in the light of linear rate of burning, apparent potential and
the newer hypotheses of reaction kinetics~ such pressures for pro#nts consisting of only NC, NG
as that of Muraour) 16)H.Muraour$ RevGenSci and Centrality) 35)Anon7 “ordnance proof
44, 567-71 (1933)(A resum~ and elaboration of Manual”, Aberdeen Proving Ground, Md,7-24
theories of burning and detonation of proplnts and 36) L.Shulman et al, PATR FRL-TR 41(1961)
HE’s discussed in earlier papers of Muraour et al)
17) H, Muraour & W. Schumacher, MP 27, 87-97 Burning and Burning Characteristics of Propellants,
( 1935) (Burning rates of colloidal proplnts at atm Experimental Procedures. The simplest method
pressure) 18) A. F. Belyaev, ActaPhysiochim 8, for experimental detn of burning rate is to
763-72(1938); ZhFizKhim 12, 93-9(1938); measure the time required for a long strand(or
DoklAkadN 24, 254( 1939) (TheOry Of b~ning) stick) of proplnt to burn in a closed vessel
 B 350

either in air or in an inert gas(such as nitrogen) the burning rates of proplnts at pressures to
at a desired pressure and temperature. Electronic 3500psi and in the temp range -40 to 71°. Full
timing apparatus(Refs 1,2,3,4,5 & 7) or other description of the apparatus and technique are
devices(Ref 10) may be used for measuring the given) 8)P .Tavernier & P .Prache, MP 34,
time of burning. A description of Crawford-type 255-75( 1952) (Detn of rates of burning in inert
strand-burning apparatus suitable for testing all atmosphere. Description of apparatus) 9)J .W.
types of solid proplnts is given in Ref 15,p 91. Linnett, {‘Methods of Measuring Burning
A closed bomb type apparatus for measuring Velocities”. A paper reported in the 4th
rates at const pressure is described in Ref 16. Symposium on Combustion”, Williams &
Devices permitting one to interrupt the burning of Wilkins Co, Baltimore, Md(1953), 20-35(59 refs)
a proplnt at any preselected time and to quench 10)F .H.Garner et aI, C‘A Comparison of
it are described in Ref 12 and in Ref 15,pp 177. Schlieren, Shadow and Luminous Methods of
This method permits examination of partially Determining Burni,ng Velocities”. A paper
burned proplnt grains reported in the “4th Symposium on Combustion”
Refs: 1 )H.Muraour & W. Schumacher, Chim & Williams & Wilkins Co, Baltimore, Md(1953),
Ind(Paris) 33, 556-8(1935) & CA 29, 3901(1935) 386-92(17 refs) ll)G.Seitz, Explosivst 1955,
(Method of detg rate of burning of colloidal 173-8( Investigation of burning of proplnts in a
proplnt in an inert atmosphere, such as N, and at closed combustion bomb) 12)P .Miaud, MP 38,
atm pressure) 2)H.Muraour & W.SchumacherY MP 181-8( 1956) (Investigation of burning of proplnts
27, 87-97(1937) & CA 31, 7649( 1937)( Cylindrical by means of an apparatus permitting
sticks of proplnt, 2-3mm in diam were fastened extinguishing of the proplnt at any desired
in a vertical position and ignited at the top. The moment and then reigniting it) 13) A. G. Magar,
time necessary for flame to travel a distance of “Methods of Procedures Used in Determining the
20cm was measured by a chronometer and the Burning Rates of Solid I?ropellents, “Frankford
speed of burning? VI ~ per sec was calcd. This Arsenal, Philadelphia, Pa, Memorandum Report
value agreed within exptl error with the one No MR-703, Ott 1958, OCO Proj No TSI-15, DA
calcd from the equation V=a + bp) 3)H.Muraour, Proj No 5S02-06-001 14)A.R.Shoff & E.D.
Chim & Ind(Paris) 47, 476-77(1942) & CA 37, Harvey, “Improved Technique for the
5592( 1943) (Detn of rate of burning of proplnts in Determination of Burning Rate vs Pressure
inert atm at pressures of 10,25 & 50kg/cm2 using Relationship in Solid Propellants”, Allegany
a steel bomb provided with a glass window for Ballistics Laboratory ABL/B-17(1958)(Not used
observation) 4)B. L. Crawford, Jr & C..Hugget, as a source of info) 15)Warren(1958), 90-91 &
OSRD Rept 4009( 1944)( Direct measurements of 177-8 16)K.Schriver, Explosivst 1959, 260-2
burning rates of proplnts by an electric timing (Description and drawing of an apparatus for the
method) 5)B .L.Crawford, Jr et al, AnalChem detn of burning rates of proplnts at constant
19, 630-33( 1947) & CA 41, 7117(1947) [Detailed pressure)
description of a simple and convenient method
for the direct measurement of the linear burning Burning and Burning Characteristics of Propellants
rate of proplnts is given, including a drawing of for Rockets. ‘‘Burning” in rocket technology
the apparatus. The time required for a long, refers to the interaction of oxygen molecules of a
end-burning strand to burn a measured distance gaseous, liquid or solid oxidizer with fuel
(such as 5“ ) is recorded electrically. Burning molecules, resulting in a chain of extremely
along the side surfaces of grains is prevented by complex reactions that take place when the
restrictive coating. Burning is usually conducted molecules rearrange to yield oxidesz water,
in an atmosphere of N at high pres sures(up to gaseous elements and/or small amts of other
2000psi) at a temp of 25°. For example, the mol ecul at specie s(Ref 29)
average burning rate of a proplnt contg NC Two kinds of proplnts are used in rockets:
(13.25%N) 54.0, NG 43.0 & diethyldiphenylurea solid arid liquid. Solid rocket proplnts can be
3% at 1000psi and 25° was found to be 0.5082 either colloidal double-base or composite
in/see] 6) H. Muraour, Chim & Irrd(Paris) 62, proplnts, while liquid proplnts can be either mono-
22-5(1949) & CA 44, 329(1950 )( Experimental detn or bipropellants
of the rate of burning of proplnts) 7)V. Lindner, The burning of double-base rocket proplnts
PATR 1820( 195 l)(Development of the Crawford proceeds in parallel rows in a manner similar to
-type strand burning apparatus to permit detn of the burning of proplnts described under ‘ ‘Burning
 B 351

and Burning Characteristics of Propellants for the stoichiometric ratio(Ref 25,pp 88-107)
Artillery Weapons and Small Arms”, where If the process of burning of any rocket
several theories of burning are menrioned. To proplnt(except those contg inorganic ingredients)
these may be added the theory developed in 1950 is considered to go to stoichiometric completion?
by Crawford et al(Ref 10). They consider the the end products would be C02, CO, nitrogen and
burning of double-base propInts as occuring water. However, because of extreme temps
physically in three distinct zones identified as the developed by the gases during burning, considerable
foam, the fizz and the flame zones. Since burning dissociation and other reactions can take place
takes place in parallel Iayers, it can be considered giving products such as hydrogen, solid carbon,
as one-dimensional and which progresses in a oxides of nitrogen, ammoniay hydrocarbons~ etc.
direction perpendicular to the surface of the Under the conditions normally encountered in
proplnt and which passes through each zone rocket combustion chambers Y it is considered that
sequentially. This process is described more the time required for the passage of the gas from
fully by Warren(Ref 25,pp 98-100) the reacting surface to the exhaust nozzle is
The burning of composite rocket proplnts is sufficient to allow reasonable approach to chemical
more complicated because they contain many equilibrium(see also Ref 10lp 3)
ingredients. Several oxidizers and many fuel The rate of burning of a solid double-base
binders are used to formulate composite compns. proplnt at a given initiaI temp can be calcd by the
The burning of this class of comparatively recent same formula as given under “burning and Burning
proplnts has not been as weIl explored as the Characteristics of Propellant for Artillery Weapons
older NC-NG-base ~opInts. Both Geckler(Ref and Small Arms”. However, according to Warren
21a) and Huggett(Ref 24,p 565) present a good (Ref 25,pp 92-3), when rocket proplnts were being
review of die burning mechanism as it is developed during WWII, the exponential formula
understood today(see also Ref 25,pp 1OO-1) (Eq 2) was selected on the basis that proplnts
The liquid rocket proplnts are introduced such as JPN followed this relationship very well
into the combustion chamber of a rocket through JPN is a solventless extruded proplnt
an injector in the form of droplets. The droplets which was used extensively during WWII for
then vaporize at their surface and the vapors propelling rockets. Its compn was: NC(13. 25%N)
start to burn. The mechanism of burning differs, 51.5, NG 43.0, DEtPh 3.25, EtCentr 1.0 and
however, depending upon whether the proplnt is a K2S04 1.25% with added carbon black 0.2 and
monopropellant or bipropellant, and, if a candellilla wax 0.08%(Ref 25 ,pp 5 & 9)
bipropellant, whether it is bypergolic or The exponential formula is given in Ref
nonbypergolic 25Yp 92 as:
In the monopropellant system each droplet I=BPn
is like every other and the vapors produced are where r is the linear burning rate expressed in
the same in composition(consisting of a fuel and an in/secY P is pressure in psi developed in the
oxidizer). When the se vapors are heated to their combustion chamber of a rocket and B and n are
ignition point(by means of a special igniter)$ they empirical constants characteristic of the proplnt
burn without any air being introduced from outside at a given temp(see also Refs 29 & 30)
In the bipropellant system two liquids, one a Solid rocket proplnrs, being required to
fuel and the other an oxidizer, are introduced function under steady-state pressure conditions
through separate injector nozzles into the much lower than the max pressure under which
combustion chamber to form droplets of each artillery proplnts burnt have max burning rates
material. Mixing of droplets (or of their vapors) correspondingly lower than those of artillery
produces a combustible material which in proplnts(Ref 21a)
nonbypergoiic systems is ignited in a manner Wimpress(Ref 11 ,p 17) prefers to write the
similar to monopropellant systems. When exponential equation as follows:
bypergolic systems are used, the burning of the B=@(pl /lOOO)n
vapors begins spontaneously upon mixing of two where B is the linear rate of burning in in/see}
substances and no igniter is required. For p 1- pressure in the combustion chamber in psi,
optimum performance with bipropellants, it is /3 - a constant at a given temp which represents the
necessary that the fuel and oxidizer be fed in a linear burning rate of the proplnt at 1000psi and n
ratio which will produce complete combustion, and is a measure of the sensitivity of the burning to
hence maximum energy release. This is known as changes in the pressure. The term(pl /1000) is
 1

B 352

used instead of the pressure directly merely temperature. The pressure exponent n is usualIy
because it simplifies numerical calcns and aids an average of the individual slopes of the
somewhat in comparison of the characteristics of rate-press ure(log-log) curves for each temp. B1
different types of proplnts and To are obtained from the experimental data by
In general, homogeneous proplnts, such as plotting l/r against temp in the chamber T and
double-base colloidal proplnts, have a value of n determining the slope and intercept of the
in the range 0.6 to 0.8,whereas heterogeneous resulting straight line. The constant To has some
proplnts, such as BkPdr or composite proplnts, theoretical significance since it represents the
have a lower value. The effect of the temp on temp at which burning would take place instantan-
burning rate is primarily reflected by a change in eously. Hence, this should be the surface temp.
the coeff ~. Temperature in many cases also Values for To, calcd from data obtained on some
effects the exponent n; but for pressures at which experimental double-base compns tested in small
rocket motors normally operate, the changes in n rockets motors, ranged from 1650 to 369°F. The
may be considered negligble ignition temp of double-base proplnts is believed
Following are average burning-rate constants to be ca 400 °F(Ref 25,p 94)
for typical rocket proplnts Burning characteristics of some solventless
-extruded double-base proplnts at a given pressure
and initial temp are appreciably faster near the
center of the web(ie toward the end of burning)
~, in in/see at:
than at the surface of the grain. This increase is
Propellant 0° F 70°. .F.— 140° F
—— . n — probably due, at least partly, to heating of the
grain by energy radiated from the burning gases
JP 0.71 0.551 0.671 0.815 and to a lesser degree from heating of the motor
wall with correspondingly greater radiation of
JPN 0.61 0.564 0.651 0.752 energy back to the burning surface(Ref 10,PP
18-20). This increase in burning rate should not be
Russian 0.70 0.250 0.290 0.337 confused with that caused by erosion(see Burning
Cordite Erosive of Propellants)
When some solid proplnt grains,
particularly those with relatively long circular
channels available for gas flow, are fired in
Compn of JPN is given above. JP contained rockets$ there are frequently observed certain
NC(13.25%N) 52.2, NG 43.0, DEtPh 3.0, DPhA 0.6 periodic pressure oscillations. These resonating
& KN03 1.2% with added nigrosine dye 0.1%; pressures sometimes reach amplitudes high
Russian Cordite contained NC(12.2%N) 56.5, enough to cause the grain to crack and? in some
NG 28.0, DNT 11.0 & EtCentr 4.5% with added cases, ultimately to rupture the rocket chamber.
candelilla wax 0.08% The average burning rate for the proplnt during
Based on the calcd values of ~’s, the these oscillations is always higher than expected.
proplnts JP and JPN may be considered as This phenomenon of unstable burning is known as
‘ ‘fast-burning ‘‘~ while Russian Cordite is resonance burning [See under Burning, Unstable
‘ ‘slow-burning” [in Rocket Motors)]
The influence of composition on burning rates Experimental procedures for detn of burning
of propellants is discussed by Warren(Ref 25,pp rates of rocket proplnts are practical Iy identical
967) with those described under “Burning and Burning
A mathematical discussion on influence of Characteristics of Propellants for Artillery Weapons
temp on burning rates of proplnts is given in Ref and Small Arms”. The method described by
10,pp 18 & 83-4 and in Ref 25,pp 93-4. The Warren(Ref 25,pp 90-1) uses a modified Crawshaw
formula given in Ref 25 is that of A. D.Crow & strand-burning apparatus. This method is used
W.E.GrimshawY PhilTrRoySoc 203A, 387(1932), with solid strands ca 1/8” in diam and 7“ long
which is as follows: and which are coated with a plastic so that they
1
burn from one end only
“* - Other methods are given in Refs 2 & 3
where To is a constant which is dependent upon This section was reviewed by Dr J .P .Picard
the compn of the proplnt and has dimensions of Re/s: l)R.E.Gibson, OSRD 943 or pBL 27888
 B 353

(1942 )(Discussion on burning rates of rocket Baltimore, Md(1953), 865-80 21a)R.D,Geckler,

double-base proplnts andthe possible effects of “The Mechanism of Combustion of Solid Propellants”
changes in NG and total volatile content on the in “Selected Combustion Problems-Fundamerltals
burning of jetpropulsion tube proplnts) 2)A. and Aeronautical Applications”, AGARD
Strasser, PATR 1235(1943)(Burning rates detd by Publication, Butterworths, London(1954) 22)S.S.
closed bomb tests of 3/8” x 1/16” stick double-base penner & P .p .Datner, “Combustion Problems in
proplnts of various compns) 3)A.Strasser, PATR Liquid-Fuel Rocket Engines”, in 5th Symposium
1474(1 944)( Burning characteristics of 3/8” stick on Combustion, Reinhold, NY(1955), 11-28(A
rocket proplnts) 4)H.S.Seifert et al, AmJourPhysics review with 84 refs) 22’a)Anon, “Milit~Y
15, 122(1947 )( Liquid proplnts) 5)G.J .Mueller, Explosives”, TM 9=1910(1955), 229-31 22b)L.
PATR 1637(1947)(Burning and other characteristics Crocco & S. I. Cheng, “Theory of Combustion
of stick rocket proplnts) 6)S.S.Penner$ JApplPhys Instability in Liquid Propellant Rocket Motors”,
19, 392-8(1948) & CA 42, 6512(1948)(Effect of B utterworths, London(1956) 23)D.Altman & S.S.
radiation on rate of burning of solid fuel rocket Penner, “Combustion of Liquid Propellants”, in
proplnts) 7) L. H. Eriksen, “Investigation of VOI 2 of B. Lewis et al, “High-Speed Aerodynamics
Asphalt-Perchlorate and Resin-Perchlorate Rocket and Jet Propulsion Combustion Processes”$
Propellants”, PATR 1676(1948) 8)S.S.Penner, Princeton Univ Press, Princeton, NJ(1956),pp
JApplPhys 19, 511-13(1948)&CA 42, 8475(1948) 470-5 13(70 refs) 24)C.Hugget, “Combustion of
(The theory that burning rates of rocket proplnts Solid Propellants”, in the above book by Lewis
increase slightly with an increase in radiation et al,pp 514-74(98 refs) 25)F. A. Warren Y “Rocket
path length was verified experimentally for two Propellants”, Reinhold, NY(1958), 88-107 &
double-base rocket proplnts) 9)W.G.Thummel, 137-40(Burning and burning rate of rocket
PATR 1725(1949)(Burning characteristics and propellants) 26)J .Taylor, “Solid Propellant and
other props of an experimental plastic rocket Exothermic Compositions”, Interscience, NY(1959),
proplnt) 10)G.P.Sutton, “Rocket Propulsion 100-4(Burning rate of rocket proplnts) 27)J,
Elements”, Wiley, NY(1949), 160-1 ll)R.N. Delacarte et al, MP 41, 223-84( 1959)(Contribution
Wimpress, “’Internal Ballistics of Solid-Fuel to the study of burning of composite rocket proplnts )
Rockets”, McGraw-Hill, NY(1950), 16-28 12)B.L. 28)P.Tavernier & J. Boisson, him 41, 285-98( ~959)
Crawford, Jr et al, JPhysCollChem 54, 854-62 (Theoretical study of burning in a channel of a
( 1950)(Mechanism of burning of doubIe-base perforated rocket proplnt block. After establishmknr
proplnts) 13)0. K.Rice & R.Ginell, Ibid 54, of the fundamental equation for the flow of gases
885-917 (1950 )( Theory of burning of double-base in a channel, the authors examined the influence
rocket proplnts) 14)W.H.Avery, Ibid 54, 917-28 of the proper damping of the block, of the erosive
(19> O)(Radiation effect in rocket proplnt burning) burning of the proplnt and of the widening of the
15)R.G.Parr & B. L.Crawford, Ibid 54, 929-54 channel on the functioning of a rocket. These
( 1950)(A physical theory of burning of double-base effects can cause increases in pressure as much
rocket proplnts) 16)C.W.Tait er al, JetPropln as 10 times that of normal) 29)Rocket Encycl
(JARS) 21, No 85,pp 83-8(1951) &CA 45, 9270 (1959), 60-1 30)DictGuidedMiss iles(1959), 105
( 1951 )(Method for detg burning rates of liquid (See also Refs under Combustion)
rocket proplnts) 17)kl.SummerfieldJ JetPropn
(JARS) 21, 108-14(1951), “A Theory of Unstable Additional References on Burning and
Combustion in Liquid Propellant Rocket Systems” Burning Characteristics of Propellants
18)A.Whittaker et al, <‘Burning Rate Studies” A)H.Muraour, BullFr 39, 841-6( 1926)(Laws
NAVORD Rept 1999(NOTS 599), US Naval governing burning of colloidal proplnts) B)H.
Ordnance Test Station, China Lake, Calif(1952) Muraour, BullFr 39, 846-52( 1926)( Influence of
19)Kirk & Othmer 11(1953), 766, 774 & 776( Burning temp on the burning rate of proplnts) C)H.Muraour,
rates of some rocket proplnts) 29)R.p .Smith & BullFr 41, 24-32( 1927)( Burning of colloidal
D.F .Sprenger, “Combustion Instability in Solid proplnts; the role played by radiation) D)H.
Propellant Rockets”, in 4th Symposium on Muraour, CR 191, 713-15 (1930 )( Influence of
Combustion, Williams & Wilkins, Baltimore, Md radiation on burning of colloidal proplnts in a
(1953), Pp 893-906 21 )L.Crocco & S. L., Cheng, closed vessel) E)A.M.Ball, IEC 23, 498-501
“High Frequency Combustion Instability in ( 1931) & CA 25, 2852(1931)(Burning temps of
Rockets with Distributed Combustion”, in 4th various smokeless proplnts) F)C.G.Dunkle, IEC
Symposium on Combustion? Williams & Wilkins, 23, 1076( 1931)(Correction of an error in the paper
 B 354

by Ball)(See previous ref) G)A.M.Ball, IEC 23, log(1000b)= 1. 214+0. 308 T/1000( for dry proplnts)and
1077( 1931)(Reply of Dr Ball to Dunkle) H)H. Iog( 1000b)= 1. 188+0. 308 T/l COO(for proplnts with
Muraour, BullFr 49, 268-74( 1931 )( Influence of 0.6% moisture. These equations do not hold for
moisrure on the rate of burning of proplnts) I)H. proplnts contg large amts(15-20%) of ‘Centrality]
Muraour & G. Aunis, CR 192, 90-2(1931 )(Influence X)H.Muraour, Chim & Ind(Paris) 49, 254-5(1943) &
of loading density on burning of proplnts) J )H. CA 39, 3161(1945); MAF 20, 145-8( 1946)( Influence
Muraour & G. Aunis, CR 192, 418-21 (1931 )( Burning of the variable “time” on the burning of colloidal
of colloidal proplnts contg vaselin) K)A.D.Ciow & proplnts in a closed vessel) Y)A.L.Birrill, PATR
W. E.Grimshaw, PhilTtRoySoc 230A, 387-41 1(1932) 1580(1945)(DiAcussion on the burfiing characteristics
& Nature 131, 60-1(1933); CA 26, 2057(1932) & of proplnts prepd from NC modified by treatment
27, 1512(1933)(A mathematical expression, with small amts of metallic catalysts. The presence
different from that of Muraour, is proposed for of a nickel catalyst in some proplnts showed only
detg burning rates of colloidal proplnts) L)G. a slight improvement in ballistics in comparasion
Sugot, MAF 12, 821(1933 )(Burning of progressive with non-catalyzed proplnts) Z)H.MuraourJ
-burning proplnts) M)H.Muraour & G. Aunis, CR Chim & Ind(Paris) 50, 105-8, 168-72(1943); CA
203, 117-19(1936) & CA 30, 6199( 1936)( Experiments 39, 3161(1945) & 40, 2986(1946); MAF 20, 637-42
with a proplnt contg guncotton 66, NG 25 & ( 1946) [Discussion on the relation b etw the rate of
ErCentr 9%, so shaped as to burn with const burning of a colloidal proplnt, V, and its calcd
surface, showed rhat the rate of increase of absolute temp of expln, T 1
pressure is proportional to the pressure as given Note: Equation logV= 1.37+ 0.27 T/1000, discussed
by the equation dp/dt = kp, where k is a consrant) in the above papers, was changed by H. Muraour &
N)J .Dupuis, MAF 17, 799-830( 1938)(Discussion on G.Aunis, CR 225, 381-3(1947)& CA 42, 2431
the laws of burning of colloidal proplnts) O)H. (1948), to Iogv= 0.13+ 0.54TB1 /1000 where V is
Muraour & G. Aunis, CR 206, 1723-6( 193d)(Burning diminution(in mm per see) in thickness of grains
of colloidal proplnts in parallel rows) P)J. of proplnt and TB I . temp reached after NO has
Dupuis & M. Chalvet,’MAF 18, 37-@1939)(Burning completely disappeared] AA)H.Muraour et al,
of proplnts in a Krupp-Schmidt bomb) Q)H. MAF< 22, 5 17-93(1948) & CA 44, 8659( 1950)(Detn
Muraour & G.Aunis, MP 29, 197-203 & 211-15(1939) in bombs of “vivacity” of burning of colloidal
& CA 34, 185 l(1940)(Verification of the law of proplnts by using the expression K, ET~pdt) BB)
burniu 61 colloidal proplnts when fired in a H. Muraour & G.Aunis, MAF 23, 859-66(1949)
Viei)le bomb) R)G.J.Mueller, PATR ,1017( 194O) (Study of burning characteristics of colloidal
(Burning characteristics of standard Pyro and proplnts of different compns, forms and sizes)
FNH proplnts) S)P.Varrato, PATR 1022 and 1043 CC)H.Muraou & G. Aunis, CR 228, 818-20(1949)&
( 1940)(Investigation of the method of detg the CA 43, 5189(1949)(Study of the laws of burning of
burning rate of pelleted black powder. The colloidal proplnts at pressures 50 to 100kg/cm2)
“open-pipe” method) T)G.] .Mueller, PATR 1050 DD)R.E.Gibson, Edit of ‘ ‘Symposium on Kinetics
( 1940 )(Detn of “quickness’ of std Pyro & FNH of Propellants”, JPhCoHChem 54, 850-53(1950)
propellants) U)G.J.Mueller, PATR 1167(1942) (Elementary ideas concerning the burning of
(Effect of grain form on burning characteristics of solid proplnts) EE)B.L.Crawford, Jr et al,
proplnts) V)B.J .Isaacs, PATR 1223(1942)(Rate Ibid 54, 854-62( 1950)( Mechanism of burning of
of “burning of proplnts at low pressures) W)H. double-base proplnts) FF)Jacques & James
Muraour, BullFr 9, 511-16(1942) & CA 37, 6526 Basset, CR 231, 649-51(1950) & CA 45, 1769(1951)
( 1943); Chim & Ind(Paris) 47, 602-6(1942)& CA [Investigation of burning rates of five double-base
40, 2985(1946) [Reasons are given justifying the proplnts and one chlor~te proplnt subjected to
selection of the equation V = a + bP rather than pressures up to 10000 kg\cm2 showed that the
V= bP. Here, V is the variation in rate of burning linear equation betw the rate and pressure
as a function of pressure, P$ expressed in developed by Muraour and discussed in CR 187,
kg/cm2; V is actually diminution in mm per sec 289(1928) & CA 22, 3992(1928) does not hold even
in thickness of grains of proplnt; a is a constant at pressures of 1000 kg/cm2 or less] GG)H.
equal to 10mrn for all proplnts; and the coeff b is Muraour & J .Fauveau, Chim & Ind(Paris) 65, 53-5
an exponential function of absol temp of expln T; (1951) & CA 45, 7353( 1951)LThe laws of burning of
its log being a linear function of T. For T in the colloidal proplnts in nitrogen at pressures from
range 1500 to 40000Kzlrid for P betw 25 & 4500 100 to 10000 kg/cm2. Remarks on the paper of
kg/cm2, b may be calcd from the equations: J & J. Bass et(see previous ref)] HH)J .D.Huffington,

.—- ——
1
 B 355

TrFaradSoc 47, 864-76(1951)& CA 46, 2297(1952) DoklAkadN 135, 913-16(1960) & CA 55, 26445
(Burning characteristics of cordites) Il)H.Muraour (1961). Engl transln by Consultants Bureau, NY
& G.Aunis, Chim & Ind(Paris) 67, 920-6(1952) & 11, Chemical Technology Section 1961 ,pp 193-5
CA 46, 10623 (1952 )( Experimental verification, (5 refs)(Study of burning of ballistites) YY)L.
using some French and foreign proplnts, of the Shulman et al, FRL-TR-41, PicAran(1961)
validity of Muraour’s equations for the relation (Investigation of propInts Ml, M2, M6, M1O, M15,
betw rate of burning and the calcd absol temp of M 17, T-28, T-34 and T-36 in a closed bomb test
expln) JJ)P.Tavernier & P .Prache, MP 34, at temps ranging from 21° to+52°C gave essentially
255-73(1952) & CA 48, 11060(1934)(Burning rates the following results: burning rates remained
of proplnts under high pressure in an inert s ratic or decreased 1-2% per 10° drop in temperature;
atmosphere) KK)G.Seitz, Sprengtechnik 1952, maximum pressure developed was 7% less at -52°
221-27 & Explosivst 19!53, 15-18(Discussion on than at ambient temps)
influence of geometrical form of propInts on their
consumption by burning) LL)M.Hunt et al, Burning and Burning Characteristics of
PhysRev 92, 542(1953 )( Surface temps of burning Pyrotechnic Compositions. This subject might
double-base proplnts detd betw 800° at 1000psi) include data on burning rate(or time)$ luminous
MM)H.Muraour & G. Aunis, MP 35, 287-301(1953); intensity(in candies), heat of combustion and some
Ger translation by A.Schmidt in Explosivst 19S4, other props. Some work on this subject has been
154-7 & 1955, 6-9(Detailed description of work done in the US, such as at PicArsn, Dover, NJ
done in France between 1884 and 1950 on the (Refs 2,13,16,17,18,20 & 23) and at NavalOrdLab
determination of burning characteristics of (Refs 8,9,10 & 21). Some Brit data are given in
colloidal proplnts. This work was begun by Refs 4 & 12 and some French data in Ref 5. See
Vieille & Sarrau and then continued for over 30 also Refs 11 & 24
years by Muraour. About 60 refs are included in Shidlovskii(Ref 15) discusses the theory of
the paper) NN)G.Schweikert, Explosivst 1954, burning pyro compns and gives formula for detg
58-64, 86-92 & CA 48, 14209( 1954)( Burning of their rates of burning. He lists the linear rates of
proplnts; calcns based on a new integral precept, burning in mm/see for the following stoichiometric
$~p dt) 00)P.Tavemier et d, MP 36,253-66 binary pyrotechnic compns when compressed to
(1954) & CA 49,16438( 1955)( Improvements in densities 0:7-0.9: S + KC103 2, S+ Ba(C103)22,
measuring burning rates of proplnts in an inert charcoal +KC1036, charcoal + Ba(C103 )2 2. S,
atmosphere) PP)P.Tavernier & C. Napoly, Ml? charcoal + KNOa 2, charcoal+ NaNO~ 1,
31, 217-23( 1955)(A presentation of the speed of charcoal + Ba(N03 )2 0.3, sugar+ KC103 2.5,
burning as a function of pressure in a proplnt sugar + Ba(C103 )2 1.5, sugar+ KN03 1,
contg NGu) QQ)A.I.Rubin, PATR 2237(1956) sugar+ NaN03 0.5, sugar+ Ba(N03)2 0.1,
(Analog computer computation of propellant linear shellac + KC103 1, shellac+ Ba(C103 )2 1,
burning rate) RR)M.Weinstein & A. O. Pallingston, shellac + KN03 1, shellac+ NsN03 1 and
PATR 2240( 1956) (Burning characteristics and other shellac + Ba(N03)2 0.8
props of M2 & M9 proplnts betw 137°F and -65°F) He also gives: for illuminating mixts
SS)H.Behrens et aI, Explosivst 1956, 221-6(12 Refs) I-10mm/see, tracing mixts 2-10, signal lights 1-3.
(Study of proplnt burning at low pressures) TT)P. incendiary(thermites) I-3 and smoke mixts
Miaud, MP 38, 181-8( 1956)(In order to permit O.5-2mm/sec
examination of grains of proplnts which are only The higher the mixt is compressed, the
partially consumed by burning, a special device slower it usually burns. For exampIe, a pyro mixt
was developed. This device permits igniting the (compn nor given) compressed at 1000kg/cm2 had
proplnt in a manometric bomb by gas and then a burning rate of 5mm/see; compressed at
extinguishing burning of grains at any desirable 2000kg/cmz 4.2, at 30003.8 and at 4000 3.6mm/sec
stage) UU)P.Tavemier, MP 39, 357-79(1957) It seems that compression above 3000kg/cm2 has
(Burning of proplnts under reduced pressures in no effect on the rate of burning
containers which are not closed) VV)P .Tavernier This section was reviewed by Mr. G.
& C. Napoly, MP 39, 397-416( 1957)(Rate of burning Weingarten
of solventless proplnts as a function of pressure) R efs: l)A.Stettbacher, Nitrocellulose 13, 203-7 &
WW)J.Harris & L.Shulman, PATR 2558(1958) 224-9(1942); CA 37, 5240( 1943)( The heat and
(Burning characteristics of standard proplnts light development of incendiary and flare compns)
between 21° and -51°C) XX)P.F.Pokhil et al, 2)D.Hart & H. J. Eppig, PATR 1669( 1947)(Burning
 B 356

characteristics of binary pyrotechnic mixts) edition was not available) 16)1. M. Baumel &
3)G.W. Weingart, “Pyrotechnics”, ChemPublgCo, S. Haffner, PATR 2076(1955)(Basic research on
NY(1947’)(No info on burning of pyro compns) mechanisms of reaction and characteristics of
4)J.E .Spice & L. A. K.Stavely, “The Propagation metal-dust flashes)(Conf) 17)S. Gordon &
of Exothemic Reactions m Solid systems”, C. Campbell, PATR 2123( 1955 )( Pre-ignition and
Part 1, “Pre-Ignition Reactions”, JSCI 68,313-19 ignition reactions of the pyrotechnic smoke
(1949 )(Compressed mixts of finely divided composition zinc-hexachlorobenzene-potassium
Fe+ Ba02 or Fe+ K2Cr207 are examples of perborate) 18)G.H.Wetter, PATR 2161 (1955)(A
systems capable of undergoing self-propagating portable instrument which gives a calorimetric
incandescent reactions when ignited. It has been evaluation of the emission from pyrotechnic items,
found that in both of these systems a non along with their burning times and average candle
-incandescent reactiony called the pre-ignition power) 19)J.F.Tyroler, PATR 2165(1955)
reaction, begins at a measurable rate below the (Bibliography of methods of measuring the temp of
ignition temp); Ibid, Part 11, ‘ ‘Heats of Reaction pyrotechnic flames)(Conf) 20) E. S. Freeman &
and Rates of Burning”, 68, 348-55(1949) S. Gordon, JPhysChem 60, 867-7 l(1956)(Upon
(Measurements of the linear rate of the heating intimate mixts of finely divided alkali
self-propagating reaction and of the heat of this nitrates with powdered Mg at temps greater than
reaction in compressed binary solid mixts of an 480°, ignition ensues, accompanied by a highly
oxidizing and a reducing agent) 4a)D. Hart, PATR exothermal self-propagating reaction) 21)D.W.
1733(1949)(Burning characteristics and other props Jensen, NAVORD Rept 6221 (1958)( Pyrotechnic
of a delay powder for ammo fuzes) 5)P .Tavernier, ammunition compositions and physical data)
MP 31, 309-426(1949) [Theoretical discussion on (Conf) 22)Anon, “Military Pyrotechnics”, TM
C‘candle powers’‘(pouvoirs ~clairantes in Fr) of 9-1 370-200 (1958)(N0 info on burning of pyro
illuminating mixts; experimental values f~r more compns) 23)E.S.Freeman & G. Weingarten, PATR
than 250 mixts 1 6)A.Izzo, “Pirotecnia e Fuochi 2596( 1959)(A thermal theory for rates of
“Artificial”, Hoepli,Milan( 1950)(N0 info on propagative burning for systems which undergo
burning of pyro compns) 6a)H.J .Eppig,PATR crystalline transformations and changes in
1801(1950)(Buming characteristics & other props state) 24)H.Ellern, “Modern Pyrotechnics”,
of self-hardening pyrotechnic mixts) 7) Anon, ChemPublgCo, NY(1961)(Burning rates of some
‘ ‘Military Pyrotechnics”, TM 0-1981 (1951)(N0 pyrotechnic mixts,pp 86,90,100,120,143,223 & 230)
info on burning of pyro compns) 8) R.H.Comyn, 25) J. C. Hackett, “The Rates of Burning and
US Naval Ordnance Laboratory, White Oak,Md, Luminosity of Pyrotechnic Compositions”,
NOL Rept 215t3(1952)(Effect of P~ticle size on ARDE, GtBrit, Mem(MX) 3/62( 1962 XConf)
the burning rate of delay mixts)(Conf) 9)E.
Elzufon, NOL Rept 2261 (1952 XBurning charac- Burning Characteristics and Thermal
t eristi cs of magnesium-barium chromate and 1ead Decomposition Products of some Synthetic
chromate mixts)(Conf) 10) E. Elzufon, NOL Rept Cellular Materials. The use of synthetic cellular
2262( 1952) (Effect of loading v~iables on burning materials in various applications may lead to
characteristics of delay po wders)(Conf) 1 l)Kirk potential hazards from toxic, gaseous decomposition
& Othmer 11( 1953)( Burning rates of pyrotechnics) products if these materials ate subjected to high
12)F.Booth,TrFaradSoc 49, 272-81 (1953 )( Theory temps or if they are burned from accidental causes
of layer-to-layer burning, also known as self In the production of certain expanded
-propagating exothermic reaction) 13)J .E.Andrews plastic materials, chemical blowing(foaming)
& G. Weingarten, PATR 2047(1954) [Light emission agents are frequently used to produce a cell UI ar
characteristics of experimental safe-type metal structure. One of these agents, azo-bis-
-dust photoflash bomb (shaped burster)] (Conf) - isobutyronitn’le, designated PN, decomp by heat
14)S.Hoffner, PATR 2061( 1954)(A survey of with release of nitrogen and formation of toxic
available literature on the rapid combustion of tetramethyl-succino-nitrile(designated TSN),
metals in air) 15)A.Shidlovskii, ‘Osnovy according to the following reaction:
P irotekhniki’ ‘,( Fundamentals of Pyrotechnics),
Heat
GosIzdOboronProm, MOSCOW(1954): 13- 15( B~ning NC.C(CH3)2.N:N. C(CH3)2.CN —--+Nz +
of pyrotechnic mixts); 104-15 (Mechanism of NC.C(CH3 )2 .C(CH~)2 .CN
burning of pyrotechnic mixts and fqctors influencing The problem of toxicity was investigated at
their rates of burning)(iVote: The new, 1962, the USBurMines with regard to cellular materials
 B 357

polyvinylchloride & acrylonitrile and of foaming Ballistics(1950), 22-5 & 65-6 7)SAChiSY Ballistics
agents such as the PN mentioned above (195 1), 38-9 8)L.Green, Jr, JARS(JetPropn) 24,
R e/: H. A. Watson et al, ButMines Rept of 9-21 & 26(1954 )( Erosive burning of some composite
Investigation RI 4777, Pittsburgh, Pa(1951) explns) 9)P.Tavernier et al, MP 37, 207-15(1955)
(Study of erosive burning of colloidal proplnts)
Burning, Depressive. See Burning Regressive 10) J. Boisson,MP 30,38 l-96( 1957 )( Erosive burning
of colloidal proplnts) ll)p. Tavernier & J.
Burning, Erosive(in Guns). See Erosion in Guns Boisson, Chim & Ind(Paris) 78,487-93( 1957)
(Erosive burning of coIloidal proplnts) 12)J .M.
Burning, Erosive(in Propellants) (Erosive Effect Lenoir & G. Robillard, ”A Mathematical Method to
of Gas Flow or Erosion of Propellants). Mansell Predict the Effect of Erosive Burning in Solid
(Ref 1) was one of the first to observe that the -PropeI1 ant Rockets “ in 6th Symposium on Com-
rate of burning inside tubular proplnts was faster bustion, Reinhold, NY(1957),663-7 & CA 52,
than that on the outside. A similar phenomenon 4953-5(1958) 13) RocketEncycl(1959), 148-9 14)
was observed later by Muraour(Ref 2). No DictGuided MissiIes(1959), 105
importance was attached to this phenomenon until
it was observed also(but on a larger scale) in Burning Fuse or Running Fuse. Same as Safety
rocket motors during and after WWII(Ref 11) Fuse(see under Fuses)
Investigations of burning of solid rocket Ref: Marshall 2(1917), 536, footnote 1
proplnts have shown that higher than usual rates
of burning of some grains surfaces is due to high Burning Ground or Destruction Site. A tract of
velocities of hot gases flowing over these surfaces. land designated for destruction of ammo, expls or
This erosive effect of gas /low is probably proplnts by burning. The ground(preferably
attributable to improved heat transfer from the gas located on otherwise useless lands, such as with
to the solid phase as a result of its high velocity. gullies or other defects ), should be located at the
Erosive action takes place in regions where maximum practicable distance from operating or
combustion passages do not have sufficient inhabited bldgsy magazines, railroads or highways.
cross-sectional area for the hot gases to flow out The minimum distance must be 2400ft unless pits
toward the nozzle at a low velocity. The front or other obstructions are used to limit the range
and nozzle ends of the partly burned grain usually of fragments. In this case the appropriate
show the effects of erosive burning. In these ‘ ‘missile distance” will apply(Ref 5, seen 17-6 and
instances the final web thickness at the nozzle tables). The area should be cleared within a
end, where high gas velocities are encountered, is radius of 200ft from the point of burning, of dry
appreciably smaller than at the front end, where grass, leaves, dry bushes, and other combustible
‘$
the gas velocities ate lower extraneous materials to prevent the fire from
Several theories have been proposed for spreading. The ground around the point of burning
explanation of the erosive effect of gas flow in should be well-packed earth; free from large
proplnts(See Refs 4,5,7 & 13) stones and deep cracks. Fire-fighting facilities
The effects of high gas velocity upon linear should be available to extinguish any undesirable
burning rate can be expressed in terms of an fires and, if necessary, to “wet down” the ground
erosion coefficient. Two different methods for its betw burnings and the closing of each day of
calcn are given in Ref 13 operation. Ordinary combustible rubbish should be
The effect on the linear burning rate that is burned separately from expls or ammo at a different
related to the velocity at which hot combustion location. When destroying expls or ammo by
gas flows over the burning surfaces is known as burning, the possibility of the mass detonating
the erosive-burning e//ect(Ref 13) should be recognized and appropriate protective
For more info on erosion of proplnts see the barriers or distance separation utilized for the
Refs listed protection of personnel and property
R efs: l)J .H.Mansell, PhilTrRoySoc 207A, 243 Trucks transporting expl materials to burning
(1907) 2)H.Muraour, BuIIFr 41, 1451-61(1927) grounds should meet the requirements of Ref 5,
3)R .J .Thompson & F. T.McClure, OSRD Rept seen 22. The expl material transported should be
5831 (1945 )(Erosive burning of double-base proplnts) covered with a tarpaulin and no more than two
4)J .Corner, TrFarafSoc 43, 635-42(1947) 5) persons should ride in the cab. While the material
Corner, Ballistics(1950), 74-6 6)Wimpress, is being unloaded at the burning ground the motor
 B 358

of the truck should be stopped and as soon as the Burning of Ammunition and Explosives for
unloading is completed the expl or ammo should be Destruction. This is one of the methods used for
covered with a tarpaulin before the motor of the the destruction of expl materials which cannot be
truck is started and the truck driven away. After economically salvaged
distributing expl materials to points where Following are the rypes of expl material
destruction is to take place(no more than a one-day which can be destroyed by burning: black
supply is allowed) the truck should be withdrawn powder, smokeless proplnts, TNT, PA, Tetryl,
from the area to a safe location and remain there Expl D} pyrotechnic items, small arms ammo Y
until destruction is completed primers, fuzes, detonators, boosters, fragmentation
Material awaiting destruction should be grenades and some chemical ammo
stored at not less than the “intraline” distance The operation should be conducted in a
(see Note below and Ref 5, seen 17-4) from specially selected area, called ~’Burning
adj scent stores of expl materials. The material Ground’ ‘(qv), also known as Destruction Site
should be protected against accidental ignition or Except in special cases, such as projectiles
expln from fragments, grass fires, burning embers, loaded with Expl D, ammo and expls should not be
or the detonating impulse originating in materials burned in containers nor should expls be burned
being destroyed in large lumps because of danger of detonation
Note: lntraline distance is the minimum permitted Bulk initiating expls should be destroyed by
.betw any two bldgs within one operating line oq detonation except that small quantities(not more
in some cases~ betw bldgs, areas or locations even than 28g) can be decomposed chemically. Loose,
though actual line operations are not involved. dry expls(other than initiating expls) or proplnts
Intraline distance is expected to protect bldgs, can be burned in beds not more than 3” deep.
etc from propagation of expln due to blast effects Ignition is accomplished either by means of a
but not against the possibility of propagation due safety fuse of such length as to permit personnel to
to missiles reach a protection shelter or by a black powder
The burning of expls or ammo is conducted as squib initiated bY an electric current controlled
briefly outlined in the item entitled “Burning of from a distance or from a structure which assures
Ammunition and Explosives for Destruction”. See safety to personnel. Wet expls and ammo
also under individual itemsY such as Black Powder, require a thick bed of readily combustible material,
Bombs such as excelsior> underneath and beyond to assure
R efs: l)M.Kostevitch, “Burning Ground”, Imp that all the expls & ammo will be consumed once
d’Art Voltaire, 34 rue Richer, Paris(1927) the combustible materials are ignited. RDX is
2)US Army, Chief of Ordnance, “Safety and usually burned wet to prevent detonation. In all
Storage Manual”, 00 Form No 5994, Washington, cases the materials should be so arranged that
DC(1928), seen XI,pp 3-4 3) Anon, “Ammunition combustion proceeds in the direction opposite to
Inspection Guide”, War Dept Tech Manual, TM that from which the wind is blowing
9-1904, Washington, DC(1944), 772-7 4)R.D. When misfires occur, personnel should not
Leitch & P .R.Moyer, Bureau of Mines Information return to the point of initiation for at least 30 reins,
Circular IC 7335(1945) 5) Anon, “Ordnance after which not more than 2 qualified persons
Safety Manual”, ORD 7-224, Washington, DC should be permitted to examine the misfire
(1957 ),secns 17,22 & 27 6)B.Kanouse & C.Y. Volatile flammable liquids should not be
Ruskewicz, PicArsn, Dover, NJ; private poured over the expls, ammo or underlying
communication 1961 ) combustible materiaIs to accelerate burning, either
before or while the materials are burning
Burning, Neutral. In general, it is the burning of a Explosive dusts and scrap pyrotechnic
solid proplnt of such granulation that its surface materials previously collected into receptacles
area remains constant during burning(Refs 1 & 2) partly filled with mineral oil No 10(as described
In rocketry, the term might mean the con- in Ref 3, seen 27, paragraph 2705) are burned by
sumption of a solid proplnt chge in a rocket thrust emptying the receptacles into a shallow metal pan
chamber in a manner that results in the gas and igniting as described above(see also Ref 4)
pressure remaining constant When the burning ground becomes ufiduly
Refs: l)Ohart(1946), 23 2)Glossary of 0rd(1959), contaminated(as decided by qualified personnel)
194 3)RocketErrcycl( 1959)-not found it must be decontaminated by thoroughly soaking
it with warer and leaving it to dry. Detailed

——-— . .
1
 description of various methods of-decontamination compositions such as cellulose acetate)
may be found in SD(Supply Bulletin) 5=52, 11
J~y 1945 Burning-out of Lyddite and other Shells as con-
Parallel beds of expls prepd for burning ducted after WWI in Europe is described by M.M.
should be separated by not less than 150 ft. In Kostevitch in a pamphlet entitled “Methods for
repeating burning operations, care must be taken the Safeburning-out Lyddite and other Shells”
not to allow any smoldering or hot objects to be Talleres Gr~ficos, Buenos Aires( 1944)
left on the ground from previous burning. Burning
should not be repeated on previously burned-over Burning, Physical Law of(in Interior Ballistics).
areas within 24 hours unless the area is first M. Serebryakov published a book in 1940 on this
soaked with water and then inspected by competent subject, in Russian. An abbreviated English
personnel translation of the book was made by V.A.
Some types of expls and tracers or igniter Nekrassoff for the Catholic University of America,
compns give off toxic fumes when destroyed by Washington 17, DC, under Navy Contract NOrd
burning. Proper respiratory protective equipment, 10260, April 1, 1955
such as hose masks, airline masks, and self
- cent ained breathing apparatus should be worn Burning, Progressive. In general, it is the burning
where such fumes are likely to be encountered of a solid proplnt of such granulation that its
Fire-fighting facilities must always be surface area gradually increases during burning
ready to fight grass or bush fires, but when (Refs 1 & 2)
exceptionally large amts of expls have to be In rocketry, the term means the consumption
burned, the local fire dept should be notified of solid proplnt chge in a rocket thrust chamber
(See also Burning Ground and under individual in a manner that resuIts in a gradually increase of
items, such as Black Powder, Bombs, etc) pressure(Ref 3)
Re/s:l)US Office Cheif of Ordnance, “Safety and R efs: 1)Ohart( 1946), 23 2)Glossary of Ord
Storage Manual”, 00 Form No 5994, Washington, (1959), 223 3)RocketEncycl( 1959), 64
DC, seen XI( 1928) 2)Anon, “Ammunition
Inspection Guide”, War Dept Tech Manual, TM Burning Rate. In general, this is the rate of
9-1904(1944), 772-7 S) Anon, “Ordnance Safety consumption per unit time by burning a combustible
M~ual”, ORD 7-224, “Washington, DC(1951), material(such as a gas, liquid or solid). It can be
seen 27-13 to 27-1.5 4)Anon, “Military expressed in grams, kilograms pounds, etc per
Pyrotechnics, TM 9-1370-200(1958), 127-8 5)B. second$ minute$ hour, etc; milliters, liters, cubic
Kanouse & C. V. Ruskewicz, PicArsn, Dover, NJ; meters, gaIlons Y etc per second, minute, hour> etc;
Private communication(1962) or in millimeters, centimeters inches, etc per
s econd$ minute, hour, etc(see also Burning Rate,
Burning of Black Powder; Inhibition by Foreign Linear)
Substances is discussed by S. Bentur et al,
PrRoySoc 230,A, 33-46(1955) & CA 49, 1539-40 Burning Rate Coefficient, sometimes designated as
(1955) Burning Rate Constant. It is the interior
ballistics’ parameter ‘ ‘a” in the solid-propellant
Burning of Explosives. See Burning and Burning linear burning rate formula: r = apn, where r is
Characteristics of Explosives linear burning rate, in/see; p- pressure, psi and
‘ ‘n” the burning rate exponent. Formulae for
Burning of propellants, See Burning and Burning calcns of “a” and “n” are given in Ref
Characteristics of Propellants Re/: Rocket Encycl(1959), 61-2

Burning of Various Substances. Following are Burning Rate Constant. Same as Burning Rate
some refs on this subject: 1 )P .G.Demidov, Coefficient
“Osnovy Goreniya VeshchestvJ’Gos izdat, Moscow
( 1951) 2)R.Steinberger, “Mechanism of Burning Burning Rate Exponent. See under Burning Rate
of Nitrate Esters”, int’5th Symposium on Combustion”, Coefficient
Reinhold, NY(1955), 205-11 3)C.J.Maim et al,
IEC 47, 2521-3(1955) & CA 50, 4507-8(1956) Burning Rate Linear. This is the distance normal
(Burning behavior of some cellulose ester film to any burning surface of a solid substance(such
 I

B 360

as a propellant) consumed by burning in unit time. burning

In a rocket proplnt, the linear burning rate can be
best explained by considering an end-burning Burning Time and Equivalent Heat of Exothermic
grain, properly designed and consumed in a Mixtures. Equivalent hetit is the number of kcal
combustion chamber. The total end surface$ or liberated per them equivalent, on reaction of an
any unit area of it, would burn uniformly in an oxidizing agent and fuel. The greater the
axial direction, cigarette fashion, so that the equivalent heat, the shorter is the burning time
surface of the grain at any time would be paraHeI Based on this rule, G. C.Hale and D.Hart
to the original surface formulated several fuze powders and li steal them in
The linear rate of burning can be expressed Usp 2468061(1949) & CA 43, 5189(1949)
either in inches per second(US and GtBrit) or in
millimeters(or centimeters) per second(or minute) Burning Time of a Rocket (or Jato) Motor. There
(Europe, Asia & South .America) are several different terms used to designate
Re/.s: I) Glossary of Ord(1959), 172 2) Rocket ‘ ‘burning time”
Enclycl(1959), 253 a) Total burning time is the time elapsed from
ignition of the proplnt until its complete
Burning Rates of Explosives. See under Burning consumption. This time is also known as /iring
and Burning Characteristics of Explosives duration
b) IO-Percent burning time, as used at PicArsn,
Burning Rates of propellants. See under Burning may be defined as the time interval between the
and Burning Characteristics of Propellants point where the thrust(on a curve thrust vs time)
reaches 10% of the maximum value and the
Burning Rates of Safety Fuses. Safety fuses, corresponding 10% point on the descending portion
manufd by Ensign-B ickford Co, Sims bury, Conn~ of the curve. This time is also known as action
and others, are made in two speed ranges, namely time or actuation duration(Ref, pp 14,62,140-1 &
ca 129sec/yd and ca 90sec/yd 163-4)
Re/: Blasters’Hdb(1952), 89 This value was adopted because the
[See also D.Barrington & R. G. Warncke in beginning and end portions of the curve(thrust
USBurMines InfoCircular IC 7281, Washington, vs time or pressure vs time) are of little
DC(1944)1 significance
c) “Hercules” burning time, as used at the
Burning, Regressive(or Degressive). In general, Allegheny Ballistics Laboratory, may be defined
it is the burning of a solid proplnt of such as the time interval from the instant the thrust
granulation that its surface area decreases during has risen to 10% of its max value to a point where
burning(Ref 1 & 2) the thrust begins to drop sharply near the end of
In rocketry, the term means the consumption the burning operation. This time is designated in
of a solid proplnt chge in a rocket thrust chamber Ref,p 62 simply as burning time
in a manner that results in a gradually decreasing d).50-percerzt burning time, as used by the US
gas pressure at the region of the nozzle approach Army Ordnance, is the interval of firing
(Ref 3) operation for a solid-propellant rocket propulsion
Re/s:l)Ohart(1946), 23 2)Glossary of 0rd(1959), unit during which at least 50% of the equilibrium
91 3) Rocket Encyc1(1959), 64 pressure is obtained(Ref,p 586)
Ref.’ RocketEncycl(1959), 14,62,140- 1,163-4 & 596
Burning Shots(Delayed Shots). When the detonation Note: It may be mentioned that if the maximum
wave(produced by an initiator) is too weak to pressure in a rocket(or Jato) motor occurs after
explode the charge(such as Dynamite), it 80% of the total burning time it is sometimes
frequently sets the chge on fire. The resulting referred to as the break-up pressure
burning charge might evolve toxic fumes. If a
burning chge is seen or suspected, the location Burning Train or Igniter Train. Step-by-step
should not be approached for at least one hour arrangement of charges in pyrotechnic items by
Re/: Blasters’Hdb(1952), 255 which initial fire from the primer is transmitted
and intensified until it reaches and sets off the
Burning Time is the time during which a combustible burster charge. Explosive ammunition uses a
substance(such as a propellant) is consumed by similar series, called explosive train
 B 361

Ref:GIossary of Ord(1959), 154 method of stabilizing the reaction of a tubular

grain is to make the axial perforation
Burning, Unstable(in Rocket Motors), Very often noncircular in cross section. Noncircular
rocket propellants(solid or liquid) burn unevenly perforations have not been used in rockets for the
(intermittently) with unpredictable periodic US armed forces because the relation betw burning
high-pressure oscillations in the combustion area and distance burned for grains of such shapes
chamber. These pressure oscillations are of does not result in pressure-time curves which are
sufficient amplitude to cause distinct humming, as satisfactory as those obtained from grains with
squealing or screeching and appear on the radial holes(Ref 3,PP 129-30)
oscillograph pressure record in a v“ariet y of In regard to unstable burning in Ii quid rocket
frequencies and amplitudes. Excessive smoking proplnts, some investigators, such as Ross &
usually accompanies this phenomenon Datner(Ref 8), distinguish two main types of
Unstable burning is a very serious problem instability. The most common type, cbuggiqg,
in rocketry because the effective burning time of ‘occurs at constant low frequencies between 40 &
the rocket is lengthened so much that the 200cps(cycles per second), while the other type
trajectory of the round is seriously affected. If screaming, occurs at frequencies in excess of
it occurs in rockets launched from the ground, the 1000Ocps. Chugging can often be eliminated by
first blast might be just sufficient to move the changes in mixture ratio or injector pressure drop.
rocket out of the launcher and then the rocket Screaming is a more serious problem and is
would be propelled along the ground in an difficult to eliminate. The high frequencies of
unpredictable manner. The most undesirable screaming usually result in exceedingly high heat
feature of the unstable burning is the possibility transfer rates to chamber and nozzle walls, so
of damage or even destruction of rocket motor severe in some cases as to cause destruction of
parts(Refs 2,3,14,16 & 17) the components(See also Ref 14,pp 104-5)
When some solid proplnt grains, particularly Considerable efforts have been made in
those with relatively long circular channels attempts to explain unstable burning
available for gas flowY are fired in rockets~ there theoretically. The earliest investigator of this
are frequently observed certain resonating pressure phenomenon in solid homogenious(NC-NG) proplnts
oscillations, reaching sometimes amplitudes high was Grad(Ref I). His theory is also explained by
enough to cause the grain to crack and> in some Warren(Ref 14,p 97). Later investigators were
cases, to ultimately rupture the combustion Smith & Sprenger(Ref 7), Cheng(Refs 9 & 11) and
chamber. When this unstable burning is interrupted Green(Refs 10 & 12). Delacarte(Ref 15)
suddenly and the incompletely consumed grains investigated unstable burning of composite
are recovered, they exhibit a rippled pattern on propInts(see also Ref 14,p 98)
the surface of the perforations. As this pattern In regard to liquid rocket proplnts, the
resembIes that of a standing wave> the phenomenon earliest theory of unstable burning was that of
of unstable burning of solid rocket proplnts is Summerfield(Ref 4). This was followed by
usually called resonancefor resonant) burning(Ref theories of Crocco(Ref 5), Crocco & Cheng(Ref 6)
14,p 97) and Ross & Datner(Ref 8)(see also Ref 14,p 105)
Another term used in conjunction with More detailed discussion on unstable burning
unstable burning of soIid rocket proplnts is of solid and liquid rocket proplnts may be found in
cbu//irzg. This usually refers to an umstable the books of Sutton(Ref 2), Wimpress(Ref 3),
condition in burning when the chamber pressure Warren(Ref 14), Herrick(Ref 16) and Merrill(Ref 17)
drops below minimum value necessary to sustain This section was reviewed by Dr J .P.Picard
the burning processes(Ref 16,p 88) Re/s:l)H.Grad, CommunPureAppldMath 2, 79-102
It has been found that there are several ( 1949) (Resonance burning in rocket motors 2)G.P.
methods to stabilize the burning in central Sutton, “Rocket Propulsion Elements”, Wiley,
perforations of rocket proplnts. The most common NY( 1949), 160-1 3)R.N.Wimpress, ‘ ‘Internal
method is the drilling of radial holes through the Ballistics of Solid-Fuel Rockets”, McGraw-Hill,
grain web at even intervals along the axis, as NY(1950), 27-8, 104-10 & 122-31 4) M. Summerfield,
described in detail in Ref 3,PP 124-7. Another JARS(J etPropn) 21, 108- 14(195I)(A theory of
method of stabilization is insertion of a rod of unstable combustion in liquid proplnt rocket
nonburning material in the center of the axial motors) 5) L. Crocco, JARS(JetPropn) 21, 163-78
perforation of the grain(Ref 3Yp 128). A third (195 1) & 22, 7-16(195 Z)(Aspects of combustion
 1

B 362

stability in liquid proplnt rocket motors) 6)L. Burnt(All-Burnt). A term used in Interior
Crocco & S. I. Cheng, JARS(JetPropn) 23, 301-13 Ballistics to indicate that the proplnt chge is
( 1953)(High-frequency combustion instability in completely consumed and only combustion gases
rocket motors with concentrated combustion) 7)R. are present, This usually takes place well before
P .Smith & D. F. Springer, “Combustion Instability emergence of the projectile from the muzzle of
in Solid Propellant Rockets”, in “4th Symposium the gun. The step which follows is called the
of Combustion”, Williams & Wilkins, Baltimore, after-burnt phase. It involves the transformation
Md(1953), 893-906 8)C.C.ROSS & P .P.Datner, of energy from the hot proplnt gases at high
“Combustion Instability in Liquid Propellant pressure to rhe projectile without further
Rocket Motors-A Survey”, in C‘Selected Combustion addition of energy to the gases(Ref 1)
Problems-Fundamentals and Aeronautical Calcns of various ballistic values at
Applications”, AGARD Pub, Butteworths,London “burnt” and “after-burnt” periods are given
(1954) 9)S.I.Cheng, JetPropn(JARS) 24, 27-32 & in Refs 2 & 3
102-9( 1954)( High-frequency combustion instability Re/s: I)Glossary of ord( 1959), 6 & 11 2)
in solid proplnt rockets) 10)L.Gr-en, JetPropn Corner, Ballistics(1950), 138-42 3)SACM.S,
(JARS) 24, ,252-3( ~954)(Unstable burning of solid Ballistics(1951), 86-8
proplnts) ll)S.I.Cheng, JetPropn(JARS) 25,
79-81( 1955)@n unstable burning of solid ProPints) Burn Through.(See item b) under Burnout
12) L. Green, JetPropn(JARS) 26, 655-9(1956)
(Observations on the irregular reaction of solid Burnt Velocity(Burnout Velocity). The velocity
proplnt charges in rocket motors) 13) L. Green, of a rocket, rocket-powered aircraft, or rocket
J etPropn 28, 483-5( 1958 XSome effects of charge -powered projectile when fuel consumption
configuration in solid proplnt combustion) 14)F.A. terminates due to exhaustion
Warren, C‘Rocket Propellants”, Reinhold, NY Refs: l) Glossaty of 0rd(1959), 51 2)Dict
(1958), 97-8 & 104-5 15)J.Delacatte, Mp 41, GuidedMissiles( 1959), 105
267-84( 1959)(Study of instability of b~ning of
composite proplnts) 16)J .W.Herrick, Ed, “Rocket Burp Gun. A slang term for the submachine gun
Encyclopedia”, Aero Publishers, Inc, Los Angeles Ref: Glossary of Ord( 1959), 51
(1959), 88( Chaffing & chugging) 97, (Combustion
instability) & 386-7( Resonant combustion) 17)G. Burrowite, One of the Brit Ammotds used
Merrill, Ed, “Dictionary of Guided Missiles and during WWII: AN 74, TNT 16 & Al 10%
space Flight”, Van Nostrand, NY(1959), 126 Re/: AllEnExpl(1946), 85
(Chuffing and chugging),522(Resonant burning)
Burrows Explosive of 1914. It contained K
Burnout. In rocket technology, this term has two nitrate 56, 2,3 ,4-TNT(obtained by distn of
meanings: a) The termination of burning of a jet crude Iiq TNT) 18, Al(30-mesh, porous,
or rocket engine because of exhaustion of fuel. jagged-surfaced granules) 18, Amm perchlorate
The term should be distinguished from cut-o//, 6 & paraffin wax 2%
which impIies a cessation of burning brought Refs.’ l)F .R.Burrows & J. G. Burrows, Britp
about by means other than exhaustion of fuel; and 11582(19.14) & CA 9, 3363(1915) 2)Co1~er
b)The rupture or damage done to the combustion (1918), 684 3)F.R. & J .G.Burrows, US?
chamber because of overheating in combination 1301646(1919) & CA 13,1930(1919)
with high gas velocity. This is also Imown as
bum-tbrougb Burrows & Hoyt Explosive. An expl compn
Re/s.’l)DictGuidedMissiles(l959), 105 2) suitable for rock blasting: Amm perchlorate 54,
RocketEncycl(1959), 62-3 Ba nitrate 29.5, Al powder 1.5, Al granules 9 &
resin 3 parts
Burnout Time is the time in which a rocket motor Ref: E. H. Burrows & W. Hoyt, USp 1891500
exhausts its fuel supply. It is usually measured (1932) & CA 27, 2036(1933)
from the time of ignition
ZZe/: Glossary of 0rd(1959), 51 Burrows’ Inventions. L. A. Burrows, during his
work with the DuPont Co, obr many patents on
Burnout Velocity. See Burnt Velocity eirplosives Y igniters, initiators, fuses, explosive
rivets, electric squibs, etc
 B 363

Following is a partial list of his patents (1942)(Ignition compn for elec blasting caps
as well as those with collaborators, all assigned consisting of smokeless proplnt and a Pb salt
to the DuPont Co: of 4,6-dinitro-o-cresol) 15)L .AJ31MTOWS et al,
l)W.H.Aughey, L.’A.Burrows & W. E. Lawson, USP 2295075 (1942 )(Elec heating device for
USP 2086527(1937) & CA 31, 6466( 1937)(Elec expl rivets) 16)L.A.Burrows, CanP 411441
blasting initiator) 2) L. A. Burrows, USP (1943) & CA 37, 3607( 1943)( Blasting initiator
2086530(1937) & CA 31, 6466( 1937)(Elec contg HNMnt as base chge and DADNPh with an
blasting initiator contg an ignition compn oxidizer as top chge) 17) L. A. Burrows et al,
comprising a Pb salt of nitrophenol) 3)L.A. USP 2327763( 1943)(Method of firing expl rivets)
Burrows & W.E.Lawson, USP 2086531(1937)& 18) L,A.Burrows, CanP 411756(1943)& CA 37,
CA 31, 6467( 1937)(Elec blasting initiator contg 3943( 1943) (Blasting cap contg an igniter chge
Cu acetylide) 4)L.A.Burrows, USP 2086532 of LSt/TetryI, primer chge of LA, base chge and
(1937) & CA 31, 6467( 1937)(Elec initiator contg a chge betw the igniter & primer consisting of
LA) 5)L.A.Burrows, LLSP 2086533(1937) &’ CA dead-pressed HNMnt) 19)W.Briin & L.A.
31, 6467( 1937)(Elec blasting initiator contg an Burrows, USP 2341263(1944)& CA 38, 4448
ignition compn comprising Ag. and Hg derivs of ( 1944)(Priming mixts suitable for ammunition)
chlorinated azidodicarbonamidine and NS as a 20) L. A. Burrows et al, USP 2376474(1945) & CA
gelatinize) 6)L.A.Butrows et al, USP 39, 3556( 1945)(Nitrourea stabilized by blending
2105635(1938) & CA 32, 2357( 1938)( Ignition small amts of non-volatile acid materials, such
compn for elec blasting caps contg an alkyl as oxalic acid, etc) 2 l) L. A. BurrowsY USP
salt of Pb, such as bis-triethyl Pb styphnate) 2387742 (1945 )( Explosive rivets) 22)L.A.
7)L.A.Burrows & W. F. Filbert, USP 2118487 Burrows, CanP 428518(1945)& CA 39, 5080
(1938) & CA 32, 5413( 1938)(Prepn of polyvinyl (1945)( Blasting cap contg PETN as base chge
nitrate) 8)L .A.Burrows & G. A.Noddin, USP and DADhTPh with an oxidizer as top chge)
2123691(1938) & CA 32, 7268( 1938)(A nonviolent, 23) L. A, Burrows, USP 2388901 (1945 )(Heating
ventless elec blasting squib comprised of a device operated like a gasoline torch for expI
rigid shell contg a base chge, such as Mg & rivets) 24) DuPont Co & L. A. Burrows, BritP
Ba02, capable of generating sufficient heat to 568109( 1945) & CA 41, 2900( 1947)( ~itiating
fuse a vent in the shell; a juxtaposed chge,such compns produced by mixing DADNPh with
as Ba02, Se & NS, capable of igniting the base nitrated polyhydric al CS, such as HNMnt, and a
Chge; and elec connections for firing the solvent miscible with H20 in which DADNPh is
juxtaposed chge) 9)L.A.Burrows, USP 2173270 insol & HNMnt is sol) 25) DuPont Co, L.A.
(1940) & CA 34, 627(1940)(E1ec blasting cap Burrows et al, BritP 572056(1945) & CA 41,
contg the double salt of Pb hypophosphite with 6724( 1947)(Prepn of stable nitrourea) 26)L.A.
Pb nitrate as igniter compn) 10)L.A, Burrows, Burrows, USP 2396152(1946) & CA 40, 3606-7
USP 2173271(1940) & CA 34, 628(1940 )(Elec (1946)( Blasting cap contg PETN as base chge
blasting cap contg Ca hypophosphite and and DADNPh with HNMnt as top chge) 27)L.A.
KC103 or KN03) 10a)L.A.Burrows & W.F. Burrows & W. E.Lawson, USP 2402235(1946) &
Filbert, USP 2175249(1940) & “CA 34, 888(1940) CA 40, 5568( 1946)( BIasting cap contg PETN or
(Elec blasting initiator of the delay type and other HE as base chge and LA or MF blended
comprising a complex salt of Pb nitrate with a with a H20-insoI metal soap, such as Ca stearate,
Pb salt of nitrophenol) 11 )L.A.Burrows & as top chge) 28) F. P,Huston, L. A. Burrows &
W. E. Lawson, USP 2175250(1940) & CA 34, W. E. Lawson, USP 2412886& 2412887(1946)
681(1940 )(Elec fuze comprising Pb salts of (Boiler construction using expIs) 29)L.A.
nitrophenols) 12) L. A. Burrows & C.A. Burrows, USP 2427899(1948)& CA 42, 764(1948)
Woodbury, USP 2205081(1940) & CA 34, 7112 (Blasting cap designed to be initiated by a fuse)
( 1940)(Elec blasting initiators contg LSt and a 30)L.A.Burrows et al, USP 2556465(1951)
soln of NC as ignition chge) 13)L.A. Burrows (Explosive rivets; improvement in construction)
& C. B. Van Winter, USP 2228339(1941) & CA
35, 2722( 1941)(Elec squib contg a S1OW Burst, This term might mean: a)An explosion
ignition chge comprised of smokeless proplnt of a projectile, bomb, warhead, demolition chge,
and an oxidizer wit~or without metals such as etc, or b)A continuous fire from an automatic
AI, Mg, Zr, etc) 14) L. A. Burrows & G.A. weapon, such as an aircraft machine gun c)
Noddin, USP 2268372(1941) & CA 36, 2725-6 A rupture of a solid proplnt rocket case caused
 I

B 364

by excessive combustion pressure casing and produces fragmentation or blast

Refs: I)Glossary of 0rd(1959), 51 2) effect is known as the bursting or main charge.
DictGuidedMissiles( 1959), 105 Explosives required to serve as bursting chges
should possess high brisance, power and
Burst Center(Center of Burst). Point in the air detonation rate combined with relative
around which the bursts of several projectiles insensitivity to impact and heat so that they can
fired from AA guns under like conditions are be loaded and handled with comparative safety,
evenly distributed The explosive in the projectile must be loaded
Re/: Glossary of 0rd(1959), 63 at high densities with a minimum of cavities.
If cavities are present to an appreciable extent
Burst Diqphragm or Burst Disc(Blowout Diaphragm in the base section of the charge, the set-back
or Rupture Disc). A flat circular sheet of produced on firing may be sufficient to cause
frangible material(plastic or metal) installed premature explosion in the gun barrel. Cavities
across the pipe suppling liquid propellant to the might also cause failure of the chge to detonate
thrust chamber of a rocket. The purpose of the due to the chge pulling away from the detonator.
disc is to prevent flow of liquid until proplnt Bursting chges should not exude when stored at
pressure builds to a preselected value. The disc elevat,ed temps.
then shears open and the proplnt is released to The conventional method of loading most
flow bursting expls is by casting, but if melting of
The same type of “valve” has been used the expl cannot be achieved at the temp of
for many years as a safety vent on tanks, lines, low-pressure steam(ca 950), the Amer practice
etc ro prevent build-up of undue pressure is to use press-loading. Some countries cast
R e/s: l) RocketEncycl( 1959), 64-5 2)Dict- -loaded expls with mp higher than 95-100°; for
GuidedMissiles( 1959), 105 example, PA(mp ca 120°) was cast-loaded in
Japan and called Shimose
Bursterberger Explosives. Dynamite-type expls Bursting chges are detonated by means of
claimed not to exude, even at 100°, and not to boosters which, in turn, are initiated by
freeze even at minus 14°, were prepd by detonators and primers
impregnating spongy substances, such as Following is a partial list of HE’s which
cellulose, rotten wood or dried mushrooms with have been used in the US as bursting chges:
ohondrin or glycocol(glycine) and then adding Amatol, Compositions A,B,C & D; Cyclotol,
26 to 60% NG DBX, Edna(Haleite), Ednatol, Explosive D,
Re/: Daniel( 1902), 89 Minol, Octol, Pentolite, Picratol, Tetrytol, TNT,
Torpex and Tritonal. Expls HMX, PETN, PA,
Burster. A long, plastic or thin-walled metallic RDX and Tetryl have been used in compositions
container filled with an expl and located in the because, alone, they are too sensitive, especially
center of a chemical or smoke shell or bomb. for use in projectiles
The purpose of a burster is to break open the Re/s: l) Ohart( 1946), 36 2) Anon, “Artillery
casing of the shell(or bomb) when the fuze Ammunition”, TM 9=1901( 1950), 35-6 & 376-9
functions so that the chemical or smoke filler 3)Glossary of 0rd(1959), 64
is released and dispersed in the vicinity of the
burst. For large-caliber chemical shell, a Bursting Charge Explosive Train. See Explosive
booster is used in addition to the burster Train
Refs: 1 )Ohart( 1946), 105-6. 2)Anon, “Artillery
Ammunition”, TM 9-1901(1950), 35 & 376-9 3) Bursting Layer. A layer of hard material used
Anon, ‘ ‘Ammunition General”, TM 9.1900(1956), in the roofs of ddgouts or cave shelters in order
122 & 142 4)USSpecifications MIL-B-13922, to cause detonation of projectiles fuzed for
MIL-B-11439, MIL-B-11OO7B, MIL-B-104I2, short delay or immediate detonation before they
MIL-B-11485B, MIL-B-112 11A, MIL-B-20490, can enter deeply enough to cause great destruction
MIL-B-12028A, MIL-B-12380 and JAN-B-349 Re/: Glossary of 0rd(1959), 52

Bursting Charge (Main Charge). An explosive Bursting point of NC. Stable NC begins to
charge(filler) in a shell, bomb, grenade, rocket, burst when the decomposition velocity reaches
torpedo, land mine or sea mine that breaks the 1.5-3.o wt % per min. The decompn rate of NC
 B 365

is proportional to K = (-U/RT)( 1 + 5tU/RT2), in England in 1888, consisted of AN with small

where K is const, U the activation energy, R the quantities of permanganates and chromates
gas const, t time in reins and T the absol temp 12e/: Daniel( 1902), 89
at which decompn of NC occurs for the duration
of t Bush(Flame Bush). A slang term used at
Ref: S. Watanabe, J ChemSocJ apan, IndChemSec proving grounds to signify the pecularly-shaped
58, 625-7( 1955) & CA 50, 7449(1956) flame that emerges and arises from the nozzle
exit of some thrust chambers of rocket motors
Bursting Screens. Special screens employed in after the main control valves have been closed
testing boosters and fuzes of artiIlery ammo. and the primary combustion stopped
The test consists essentially of firing an item Re/: RocketEncycl(1959), 65
in the vicinity of a screen for the purpose of
initiating detonation of the proj ectile(by means Business End of a Blasting Cap. A colloquial
of its impacting against the screen) and for term meaning the end of a cap placed against
observing the damage inflicted on the screen. the explosive charge. It is the solid end of the
The screen may be of a series of wood planks, cap where the “base charge” is located. II-I
a piece of sheet metal$ cardboard or armor plate caps which utilize the Munroe Effect(the
Ref: Ordnance Proof Manual No 40.20, Aberdeen “shaped charge effect”), the business end is
Proving Ground, Md(1943) indented toward the base charge
Ref: A. B. Schilling, PicArsn, Dover, NJ;
Bursting Type Smoke Shel1. See under Smoke private communication 1962)
Shells
Butadiene and Derivatives
Burst pressure. According to existing military 1,3-Butadiene, Bivinyl, Erythrene or
specifications it is the particular pressure Vinylethylene [called Butadien-(1.3),
which(when applied just one time to a rocket Divinyl, Erythren, Pyrrolylen or Vinyl~thylen in
component) results in exceeding the ultimate Ger] , CH2:CH.CH:CH2; mw 54.09, CO1, odorless,
strength of the material involved. Different flammable gas; fr p -108.9°, bp -4.4°, fl p
rocket components might have different burst <22°F, auto ign temp 824°F, d 0.621 at 20°,
pressure values vap d 1.87, vap press 1840mm at 21°; S1 toxic
Ref: RocketEncycl( 1959), 65 with MAC 1000 p/million in air or 2210 mg/m3
of air, expl range 2.0-11.5% concn(Ref 9). It is
Burst Range, Horizontal distance from a gun to sol in alc or eth and insol in w. Butadiene is
the point of projectile burst produced from petroleum by catalytic
Re/: Glossary of 0rd(1959), 52 dehydrogenation of normal butylenes at low
pressures. The crude product, obtained in
Burst Wave or Blast Wave. Wave of compressed yields of 25-30%, is purified by extraction and
air caused by a bursting bomb or shell(see also distillation to give a coml product 98-99% pure.
under Blast Effects in Air) It can be prepd also by dehydrogenation of
Re/: Glossary of Ord( 1959), 52 butane in a one-step process or of ethyl alcohol
in a two-step process(Ref 8). Other props &
Burton, J(1868-1924). An Arner industrialist who methods of prepn are given in Beil(Ref 1)
specialized in the manuf of expls. Organized Scott(Ref 2) reported that butadiene heated
the Burton Powder Co. and the American High under pressure undergoes violent thermal decompn
Explosives Co and in contact with air or O it may form violently
Ref: Van Gelder & Schlatter(1927), 26 explosive peroxides. Treatment of butadiene
with strong NaOH solns(47%) destroys the
Burton’s Explosive. An expl compn patented in peroxides. Butadiene peroxide can be detonated
1888 was prepd by mixing pulverized BkPdr with by mild heating or mechanical shock. Solid
jelly consisting of a mixt of NC with NG or with butadiene absorbs enough O at subatmospheric
a soln of shellac press to make it detonate violently when heated
Ref.’ Daniel( 1902), 89 al above its mp(see also 1,3-Butadiene Peroxide
Polymer)
Buse’s Explosive. A permissible ezp, patented Greenlee(Ref 3) noted that a destructive
 B 366

expln, including a secondary gas expln, occurred oxalic acid

in a Diels.Alder reaction between butadiene & Refs: l)Beil 1, { 940} 2) C. C.Spencer et al,
crotonaldehyde under pressure. The accident JOC 5, 615-6(1940) & CA 35, 1043(1941)
resulted from failure to mix the reactants before Butadiene Ozonide Polymer, (C4H603)X, wh
heating. Hanson(Ref 4) reported that this type solid, very expl; on boiling with w forms an
ofexpln can be avoided by calcg the liq vol at aldehyde; was prepd by Harries(Refs 1 & 2). The
reaction temp and allowing 20Z free space in normal butadiene rubber( caoutchouc), [ (CaH1 *)X1 ,
the autociave forms a monotizonide, C*H1 *OQ, a chozonide,
In the oxidn of C4 hydrocrubons induced CaHt20e, and an ozone oxide, CeH1 Z04, which
by Al borohydride, [A1(BH4)3 ] , n-butane gave is solid and highly expl(Refs 1,2 & 3)
no expln, I-butene exploded after an induction Re/s: l)Beil 1, (109) 2)C.Harries, Ann 383,
period, and 1,3-butadiene exploded immediately 206(1911) & CA 5, 3519(1911); Ann 395, 259
(,Ref 5). Previous explosions of tank trucks & (1913) & CA 7,1984(1913)
steel containers caused by filling with butadiene
and other liquefied gases in excess of their Butadiene Peroxide. See under 1, 3-Butadiene
capacity are discussed by Aull(Ref 6).
Measurements of the flammability ranges of Butadiene Peroxide Polymer, - -CH.CH .00. -
butadiene and of other pure combustibles in air [-CH2.CH:CH.CH2 .00~ -y, ~tH:CH~ ~ j
were made by Burgoyne & Neale(Ref 7) mw 700-850. It was mentioned under 1,3
Refs: l)Beil 1, 249, (107), [224] & {929} -Butadiene that Scott prepd an extremely expl
2)D.A.Scott, C & EN 18, 404(1940)& CA 34, product by peroxidation of 1,3-butadiene, but
4571(1940) 3)K.W.Greenlee, C & EN 26, 1985 its structure was not detd(Ref 2). Handy &
(1948) & CA 42, 6537(1948) 4) E. S. Hanson, Rothrock(Refs 3 & 4) prepd,by peroxidation of
C & EN 26, 2551(1948)& CA 42, 9179(1948) a soln of 1, 3-butadiene in benz at 85-95°, a
5)R.S.Brokaw et al, JACS 72, 1793(1950) & CA relatively stable benz soln of polymeric peroxide
44, 5686(1950) 6) H. Au1l, Erd61 u Kohle 3, 195 which could be stored for several weeks at RT.
(1950) & CA 44, 7539(1950) 7) J. H. Burgoyne & Careful evapn of the solvent under reduced
R. F. Neale, Fuel 32, 5(1953) & CA 47, 2577(1953) pressure produced a pale yel, S1 viscous, oil,
8) Faith, Keyes & Clark(1957), 171-78 9)Sax no 1.5052 at 25 0. This oil or its coned soln in
(1957), 391 19)CondChemDict( 1961), 178 benz can be detonated by ignition or severe
Mononitrobutadiene, C4H~N02; mw 99.09, N Shock
14. 14%; lacrimato~, CO1 oil having a sweet Refs: l) Beil-not found 2)D.A.Scott, C & EN
odor, bp 118-19°, d 1.029 at 20°t n~ 1.4211 at 18, 404(1940) 3)C.T.Handy & H. S. Rothrock,
20°; was obtd on nitrating butadiene with HNO~ JACS 80, 5306-7(1958) 4)E.G.E.Hawkins,
(d 1.49-1.50), together with a dimer of butadiene “Organic Peroxides”, VanNostrand, Princeton,
as an impurity. This and other nitroolefins were NJ,(1961), 267-8
patented as possible diesel-fuel additives,
jet-propulsion fuels, insecticides & for other Butagas. Trade name for compressed butane
uses
Re/s: l) Beil-not found 2)C.S.Coe & T.F. Butaldehyde. Same as Butyraldehyde
Doumani, USp 2478243(1949) & CA 44, 1128( 1950)
Butadiene Nitrosite, C4H6N203; mw 130. 10; N Butanal. Same as Butyraldehyde
21.53%; formed when large concns of butadiene
are mixed with NO, O & N. No other info is Butanamide. Same as Butyramide
given
Refs: l)Beil 1, {942} 2)M.S.Furman, ZhFiz- n-Butane and Derivatives
Khim 18, 473(1944) & CA 39, 2923(1945) n-Butane, Butyl Hydride, Metbyletbylrnetbane or
Butadiene Ozonides. A monoozonide, C4H603, Tetrarze(called Butan in Ger), CH3(CH2)2CH3;
wh amor solid, non-expl, was prepd by bubbling mw 58.12; COI gas, fr p -138.3°, bp -0.5°, fl p
ozone into a soln of butadiene in petr eth; the -76°F, auto ignition temp 806°F, d of Iiq 0.599
diozonide, C4H606, very unstable & expl, was at 0°, d of vap 2.07 at 0°, vap press 2 atm at
not isoIated but was prepd by bubbling ozone 18.8°, sl toxic; expl range air 1.6-6.5% concn;
into a soln of butadiene in chlf; on standing, sol in ale, eth or w. Butane occurs in crude
the diozonide decompd with the formation of petroleum or is formed during its distillation;
 B 367

it can be prepd by many methods(Ref 1) Refs: l)Beil 1, (346) 2)A.F.McKay et al,

Butane is used as producer gas, raw CanJRes 28B, 683-8(1950) & CA 45, 4646
material for motor fuels Y and in manuf of (1951) 3)Ya.Yakubovich & V. A. Ginsberg,
synthetic rubber or other org syntheses. It ZhObshchKhim 22, 1534-42(1952) & CA 47,
forms various nitro compds and other derivs. 9255(1953) 4)J.Feltzin et al, JACS 77, 206-10
Liq butane was proposed by Wulff(Ref 2) for (1955) &CA 49, 4388(1955)
use in expl mixts with a solid oxidizert silica
Mononitrobutane, C4H9N02; mw 103.12, N 13.58%.
gel & Al powd
The 1- and 2-mononitro isomers, both liquids,
The growing use of Iiq mixts of butane
are described in the literature(Refs 1 & 2)
with ethane and propane requires safety
Refs: l)Beil 1, 123, [87] & [303-4] 2)Sax
precautions in order to prevent explns, especially
(1957), 946
in residences(Ref 8). This mixt is very dangerous
2-Nitroso-2-nitrobutane, CH3 .C(N02 )(NO).C2H5;
because its expln limits are low, 2 to 9% vs 9
mw 132.12, N 21.20%; wh prisms(from chlf),
co 30% for illuminating gas. Further danger
mp 58°; insol in w or ale; other props & methods
lies in the low water pressure reqd to extinguish
of prepn are given in the Ref
its flame at the burner surface and in the low
Ref: Beil 1, 124
flame-propagation velocity which makes it even
easier to extinguish. It is suggested that some Dinitrobutane, C4HsN204; mw 148.12, N 18.91%.
strong-smelling substance be added to mixts of The following isomers are described in the
butane, ethane and propane in order to easily literature: I, l-Dinitrobutane, oil, bp 197°
detect the presence of unburned vapors (partia4 decomp); forms salts which are not
Re/s: l)Beil 1, 118, (37), [79] & {261} 2)R. expl; 1, 2-Dinitrobutane, Iiq, bp 90-92° at
Wulff, USP 1772695(1930) & CA 24, 5160(1930) <lmm (Refs 3 & 3a); I, 4-Dirzitrobutane, coi &
3)Thorpe 2(1938), 172 4)Hackh’s(1944), 149 odorless liq, bp 176-8° at 13mm(Refs 2 & 6);
5)Kirk & Othmer 7( 1951), 639 6)Merck(1952), 170 2,2-Dinitrobutane, inert oil, bp 199°(Refs I & 5);
7)Encyc1Britannica 4(1952), 59 8) Anon, and 2, 3-Dinitrobutane, COI prism s(from eth), mp
Explosivst 1956, 93 9)Sax(1957), 391-2 10) 41°, dec ca 150 °(Refs 2 & 3). Other props &
CondChemDict( 1961), 178 methods of prepn are given in the Refs
Azidobutane or Butyl Azide, C4HQN9; mw 99.14, Refs: l)Beil 1, 124 2)Beil 1, (40) & {305}
N 42.39%. TWO isomers exist: l~Azidobutane
3)Beil 1, { 305} 3a)A.E.Wilder-Smith et al,
or rz-L?utyl Azide, CO1 liqY bp 106.50 at 760mm$ BritP 580260(1946)& CA 41, 2069(1947) 4)C.T.
d 0.865 at 29.5°, n~ 1.415 at 29.5°; forms an Bahner, USP 2485803(1949) & CA 44, 2876(1950)
azeotrope with methanol boiling at 68 °(Ref 3); 5)C.T.Bahner, IEC 44, 317(1952) & CA 46,
and d-2-A zidobutane, COI liq$ bp 85° at 500mm, 4930(1952) 6)H.Feuer & G, Leston, OrgSynth
d 0.862 at 25°, n~ 1.4122 at 25°; was prepd by 34, 37-9(1954) & CA 49, 526@1955)
the action of NsN3 on butyl iodide(Ref 2). 1,1,l-Trinitrobutane, C4H7N306, described in
Their expl props were not detd Conf US Rubber Co Quarterly Rpt No 25,p 10
Re/s: l)Beil 1, [305] 2)P.A.Levene et al, (Nov 1953 to Feb 1954)
JBiolChen 115, 415-18(1936) & CA 30, 8174-5 2,2,3,3.Tetranitrobutane, H, C.C(N02)2.C(N0 )2.CH9;
(1936); JChemPhys 5, 985-8(1937) & CA 32, mw 238.12, N 23.53%; wh trysts, mp 159-163%
1151(1938) 3)J .H.Boyer & J.Hamer, JACS 77, (dec); was prepd by nitrating dimethylglyoxime
952(1955) & CA 50, 1826-7( 1956) or by the addn of nitrogen dioxide to 2,3-dinitro
l- Diazobutane, CH3.CH2.CH2.CH: N?N; mw -2-butene(Refs 4 & 5). According to Gabiel et al
84.12, N 33.30%; amber-colored liq with (Ref 5), the compd reported by Miller& Hunt
unpleasant odor; was prepd by warming N-nitroso (Ref 2) was not a tetranitrobutane but a trinitro
-N-butylurethane with alc KOH or by direct addn compd melting at 119-20°
of N-nitroso-N-buty lurea to 70z KOH cooled to The expl props & performance of this compd
OO(Ref 1). Other methods of prepn are given in are described in Conf Repts(Refs 3 & 6) and
Refs 2 & 3. Feltzin et al(Ref 4) studied the others
decompn kinetics of l-diazobutane and reported Refs.’ l)Beil 1, { 305} 2) A. J.Miller & H. Hunt,
an activation energy of 20.6 kcal/mole in the JPhysChem 49, 21(1945)& CA 39, 1352(1945)
temp range 3-22°. Its expl props were not 3)A.D.Little, “Second Rpt on Synthesis &
investigated
 B 368

Testing of HE’s’’,pp 18,31,33,59,270 & 272 induction coil. The limits of its flammability
(March 1951)( Conf) 4)J.S.BeIew et al, JACS in air are 1.83% and 8.4% by vol; min ign temp
77, 1111(1955) & CA 50, 1648(1956) 5)C.E. in air is 462°, in oxygen 319°. The addn of N
Grabiel et al, JACS 77, 1294(1955) & CA 50, (39.8%, or more) or of C02(26% or more) to
1571(1956) 6) A. D. Little, “Fourth Rpt on iso-butane-air mixts produces nonflammable
Synthesis & Testing of HE’s”p 111( 1956)(Conf) mixts provided the concn of O is a min and the
Hexanitrobutane or 1,4-Di(trinitro) butane, concn of iso-butane is less than 2,5%
(02 N)3C.CH2.CH2.C(N02 )3; mw 328.12, N Re/s: l)Beil 1, 124, (40), [87] & {305} 2)G.w.
25.62%; was believed to be obtd in admixt with Jones & G.S.Scott, BurMines RI 4095(1947)&
h exanitroisobutane, C(N02)3 CA 41, 6723(1947) 3)CondChemDict( 1961), 621
H3C.CH< >
/3-Nitroso-iso-butane or 2-Nitroso-2-metby2proparre,
C(N02)a
in 1945 by Dr Schimmelschmidt of IGFarbenind (CH3)SC.NO; mw 87.12, N 16.08%; wh ndls,
when acetylene gas was bubbled into nitroform mp 76-76 .5°(in a sealed tube), and distills at
contg a little mercuric nitrate. The following 80-2°; in an open tube sublimes w/o melting; was
reactions are supposed to take place: prepd by oxidizing ter-butylamine with cold
HC:CH + CH(N02)3+CH2:CH. C(N02)3 Care’s persulfuric acid
Refs: l)Beil 1, 129 & {327} 2) E. Bamberger &
2CH :CH.C(N02)3 + 2CH(N02)3-+CH3. - R.Seligman, Ber 36, 685(1903) & JCS 84 I,
CH ~C(N02)3]2+ (02 N)3C.CH2.CH2.C( N02)3 322(1903)
Both of these compds are very powerful expls kiononitro-iso-butane, C4H9N02; mw 103.12, N
and were believed to be present in tetranitro- 13.58%. The l-nitro and 2-nitro isomers of
methane & nitroform when a reduced flow of 2-methylpropane are described in the literature
acetylene occurred in the main reaction of
Re/.’ Beil 1, 129, (42) & {327}
IGFarbenind’s method of prepg TeNMe &
Dinitro-iso-butane, C4H8N204; mw 148.12, N
nitroform from acetylene & HN03. Attempted
18.91%. TWO isomers are described in the
prepn of HeNBu by the US Rubber Co is described
literature: 1,1 -Dinitro-2-methylpropane or
in Ref 4
a, a-Dinitro-isobutane, (CH3)2CH.CH.(N02 )2,
Re/.s: 1 )Beil-not found 2) CA-not found(thnr
non-volatile oil; forms K & Ag salts which are
1956) 3) W. Hunter, “The Production of
not expl(Ref 1); and 1,2-D irzitro-iso.butane,
Tetranitromethane and Nitroform”, IGFarbenindj
(CH3 )2 C(N0._).CH2 .N02, wh tryst solid(from
Hochst-am-Main, BIOS Final Rpt 709, Item
MeOH), mp 52-3°, bp 92° at Imm, was obtd as
22,8-9(1946) & PB Rpt No 47730, OTS
the primary product in the reaction between
Bibliography of Scientific and Industrial
iso-butylene & dinitrogen tetroxide in ether or
Reports vol 4, 1041( 1947) 4)US Rubber Co,
ester medium(Refs 2 & 4). This compd is a
Quarterly Progress Rept No 6, Contract Nerd
10129, Passiac, NJ(1948), 28-9 mild expl(51% of Blasting Gelatin by Ballistic
Mortar Test); very insensitive to friction or
impact; and is stable in storage at RT 50° &
iso-Butane and Derivatives
on heating in vacuum at 100° for 40hrs(Ref la &
iso-Butarze, 2-Metbylpropane or Trirnetbylmetbane,
(called Isobutan, 2-Methyl-propan or Ref 4,p 57)(See also Ref 5)
Trimethylmethan in Ger), (CH3)3 CH; mw 58.12, Refs: l)Beil 1, 130 la)Beil 1, {328} 2)A.E.
Wilder-Smith et al, BritP 580260(1946) & CA
CO1gas, fr p -159.6°, bp -11.7°, f1 P -83°, d 0.557
41, 2068-9( 1947) 3)C.W.Scaife et al, Britp
at 200; other props & methods of prepn are
given in Beil(Ref 1) 5905 13(1947) & CA 42, 2984( 1948)( Reaction with
NH3, urea,or EtONa) 4)N.Levy et al, JCS
iso-Butane occurs as an important
1948, 52-60 & CA 42, 4906(1948) 5)A.E.
component of natural gasoline, refinery gases,
Wilder-Smith et al, USP 2472550(1949) & CA
“wet” natural gas and can be obtd by
43, 6646-7(1949)
i somerization of n-butane. It is used in org
synthesis, as a refrigerant, fuel, as starting
l,4-Butanedicarboxylic Acid. See Adipic Acid,
material for liq fuel synthesis and as an
Vol l,p A104-L
aerosol propellant(Ref 3)
The general expln hazards of iso-butane
Butanediol and Derivatives
were detd by Jones & Scott(Ref 2). Gaseous
Butanediol, Butylene Glycol or Dihydroxybutane:
mixts were ignited by sparks from a high-voltage
 B 369

C4H ,.02; mw 90.12. Four isomers are described Abel lIeat Test vaIue of 2 reins at IOO°C vs
in the literature: a or 1,2-Butiznediol, 10+ reins for NG at 82.2°. It was found to be a
CzH5.CH(OH).CH20H( Refs 1 & 5,p 404); poor gelatinize for NC of 13. I % N(Ref 9). See
/3 or 1,3-Butanediol, CH3.CH(OH).CH,. CH,.0H also discussion in Refs 3,4,7,8 & 14
(Refs 2 & 5,p 405); y or 1,4-Butanediol Refs: l)Beil 1, { 2166,2172,2176,2183,2187}
(Tetramethylene GlycoI), HO(CH2)40H(Refs 3& 2)H.FJibbert, USP 994841 & 2(1911) & CA 5,
5 ,p 392); and # or 2, 3-Butanediol, 2724(1911) 3) Brunswig, Props(1926), 14 & 22
CH3(CH.0H)2CH3( Refs 4 & 5,p 405). All are 4)Naotim, NG (1928), 238-9 5)C.!yiatignon et al,
col liquids; their props & methods of prepn are MP 25, 176,184( 1932-33) 6~?)Aubry, Mp 25,
given in the Refs 194(1932-33) 7) Davis(1943), 235 8)P.F.Macy &
Refs: l)Beil 1, 477, [544] & { 2165} 2)Beil A. A. Saffitz, “ Explosive Plasticizers for
1, 477(248), [545] & {2167} 3)Beil 1, 478, Nitrocellulose”, PATR 1638(Feb 1947)( Prepn
(249), [545] & {2172} 4)Beil 1, 479, (249), and lab tests of stability & sensitivity) 9)A.F.
[546] & { 2178} 5)Sax(1957), 392,404,405 McKay et al, JACS 70, 430(1948) & CA 42,
2,3.Butanediol-3-nitrate(Nitratobutanol), 2228(1948) IO)P.Aubertein, MP 30, 21(1948) &
CH3.CH(OH).CH.(ON02 )cH3; mw 135.12, N CA 4!5,, 353-5(1951) ll)L.M~dard, MP 31,
10.37%; Iiq, bp 44-5° at lmm$ d 1.811 at 29°, 131-43(1949) & CA 46, 11685(1952) 12)J.
n~ 1.4382 at 20°; was prepd by adding HN03 Tranchant, MP 32, 313-18(1950)& CA 47,
to 2, 3-epoxy butane 9014(1953) 13)L.Boileau & M. Thomas, MP 33,
/o\
(H3C.CH— CH.CH~). 155-7( 1951) & CA 47, 5200( 1953) 14)13elgrsno
Some of the nitrato alcohols are high expls, for (1952), 91
e xampleY the 2-nitratoethanol detonated at Butanediol Dinitrite, C4H8N204; mw 148.12,
187°, the nitratopropanol under the same N 18.91%. Three isomers are described in the
conditions decompd; results of the thermal literature: 1, 3-Butanediol Dinitrite,
sensitivity of the nitratobutanoI were not (ONO).CH2.CH2.CH(ONO).CH3, Iiq, bp 52° at
reported 41mm, d 1.075 at 25°, n~ 1.3968 at 25°; thermal
Refs: l) Beil-not found 2) P. L. Nichols, Jr et al, decompn products ate acetaldehyde, ethylene &
JACS 75, 4255-58(1953)&CA 48, 11296(1954) propyiene(Ref 3); 1, 4-Butavediol Dinitn’te,
Butanediol Dinitrate or Butylene Glycol (ONO)CH2.CH2.CH~CH2 (ONO), liq, bp 700 at
Dinitrate, C4HaN206; mw 180.12, N 15.55%. 44mm, d 1.166 at 25 , n~ 1.4028 at 25°; thermal
Four isomers are described in the literature: decom~ products are NO & y-hydroxybutyralde-
1 ;2-Butanediol Dinitrate, C H CII(ON02) - hyde(Ref 3); and 2,3-Butanedio,l Dirzitrite,
CH2(ON02), Iiq, bp 114-156a: llmm(Ref l,P CH3.CH(ONO).CH( ONO).C}13, Iiq, bp 42° at
{21@)); 1,3-Butanediol Dinitrate, 50mm, d 1.066, n~ 1.3938 at 20°; thermal
(02NO)CH2.CH2.CH( ONOZ).CH3, lt yel oil, decompn in the vapor phase gives NO &
very volatile, d 1.309 at 22°, n~ 1.4479 at acetaldehyde while in the liq phase the products
17. 5°; viscosity & index of refraction(Refs 13); are acetaldehyde, biacetyl, 2-butanol-3-one &
prepn(Ref l,p { 2172}) & Ref 6); impact 2 ,3-butanediol(Ref 2). These compds were
sensitivity 2.5-3.0 vs 0.42-0,40 for NG(Refs prepd from the corresponding diols by std lab
10 & 11); was used by Hibbert(Ref 2) in expl procedures. Their inhalation produces headaches
mixts and by Tranchant(Ref 12) as substitute R efs: l)Beil-not found 2)L .P .Kuhn & L.
for NG in double-base propellants; and DeAngelis, JACS 76, 328-9(1954) & CA 49,
1,4-Butanediol Dinitrate, (02 NO)C112 .CH2 .CH .- 2996(1955) 3)L.P.Kuhn et al, JACS 78,
CH2(ONOZ), lt yel oil, very VOI, d 1.335 at 166, 2719-22(1956) & CA 50, 14506(1956)
n~ 1.45oo at 21.2 °(Ref l,P {2176}) & Ref 13); 2-Nitro-1,4-Butangdiol, H0.CHZ.CH2.CH(NOZ ).-
impact sensitivity 3.10 vs 0.40 for NG(Ref 11); CH2.0H, is known in the form of its Na salt,
and levo-2, 3-Butanediol Dinitrat e, CH3 .CH- crysts(from methanol)
(ON02).CH(ONOZ)CH3, oily Iiq, fr p 0-4°, Ref: Beil 1, { 2177}
bp 91.5° at IOmm, d 1.297 at 20 0, no 1.4405 at 1,4-Dinitro-2,3.butanediol,O2N.CHCH(OH)2.
20°; in sol in w; was first prepd by nitrating .CH(OH).CHZ.N02; mw 180.12, N 15.55%;
levo-2,3-butanediol at 0-5 °(Ref 5). See also crysts(from 1, l-chloronitroethan e), mp 134°; was
Ref l,pp {2183 & 2187}. It is an expl comparable prepd ‘from nitromethane, aq glyoxal(CHO)2,
in impact sensitivity to TNT and in stability to methyl alc & NaOH in w kept 1 hr at 10° and
NG; a sample in storage for 4 yrs gave an neutralizing the soln with acetic acid; the
 B 370

nitromethane extract was evap in vacua. No for Tetryl

expl props were reported Power by Trauzl Test(CUP) 140.3 vs 100 for PA
Rejs: l)Beil-not found Z)H.PIaut, USP Sensitivity to Initiation, readily detonated in the
2616923( 1952) & CA 49, 11701(1955) liq state by a No 8 blasting cap as was its
1,1,4,4-Tetranitro-2,3-butanediol) (O,N),CH.CH- 50/50 mixt with DNT
(OH).CH(OH).CH(NO,),; mw 270.12, N 20.74%; Stabikty, not satisfactory for most purposes
brn liq; was first prepd from the di K-salt of Bergeim(Ref 2) in 1928 patented an expl
dinitromethane in w and glyoxal. This compd compn contg nitro-iso-butanediol dir&ate, NG,
i-s considered a useful intermediate,fuel,or NaNO s, woodmeal, CaCO, & NC. This compd
expl ingredient has also been used as an antifreeze agent and
Refs: l)Beil-not found 2)I!.Plaut, USP as a component of some expls
2544103(1951) & CA 45, 7587(1951) Refs: l)BeiI-not found 2)F.H.Bergeim,USP
1,1,1,4,4,4-Hexanitro-2,3-methoxybutanediol, 1691955( 1928) & CA 23, 708( 1929) 2a)M.S.
(O,N),C.CH(OCH,).CH(OCH,).C(NO,),, is Fishbein, VoennayaKhim 1933, No 6,3-8 & CA
described in Conf EngrgResInst 2nd Quart Prog 29, 7077(1935)(A review) 3)W.deC. Crater, USP
Rept (March 1954) and abstracted in US Rubber 2112749(1938) & CA 32, 3964(1938) 4)H. J.
Co 1st QuartProgRept No 26(Contract NOrd Hibshman et al, IEC 32, 427-9(1940) & CA 34,
10129 & 12663) 3234-5(1940) 5)J.A.Wyler, USP 2195551(1940) &
CA 34, 5283(1940) b)L.Me’dard, MP 35, ll\1-12
iso-Butanediol and Derivatives (1953) & CA 49, 5842( 1955) 7)L.Mgdard & M.
iso-Butanediol, iso-Butylene Glycol, asym Thomas, MP 36, 97-127(1954) & CA 50, 3763
-Dimethylethylene Glycol, Methyl-propanediol or (1956) 8)J.SalI& MP 36, 305-7(1954) & CA
Methyltrimethylene Glycol,C,H,,O,; mw 90.12. 49, 16218(1955)
Two isomers are described in the literature:
2-Methyl-1,2-propanediol. (H C)?IC(OH).CH,.OH Butanetriol and Derivatives
(Ref l,pp 480, (250) & [5473) and 2-Methyl Butanetriol, Methyl Glycerol or Trihydroxybutane,
-1,3-propanediol, OH.CH,.CH(CH,).CH,.OH(Ref C,H,,03; mw 106.12. Two isomers are
1,pp 480 & (2189)) described in the literature: 1,2,3-ButanetrioZ,
Ref: Beil 1, 480, (250), [5471 & (2187, 2189) CH,.CH(OH).CH(OH).CH,.OH; hygr liq with
Nitro-iso-butanediol or 2-Nitro-2-methyl-l,3 burning taste, bp 162.5-63.5’ at 15mm(Ref 1);
-propanedioZ, HO.CH,.C(NO,XCHa).CH,.OH, mw and 1,2,4-~utanettiol, CH,(OH).CH,.CH(OH).-
135.12, N 10.37%; monoclinic trysts, mp CH,.OH; syrupy liq with sweet burning taste,
147-50’; dec on heating under lOmm pressure; bp 190-l’ at 18mm(Refs 2 & 4). Other props &
readily sol in w or ale; was prepd by addg a methods of prepn are given in the Refs. These
little KHCO, to a mixt of nitroethane, compds yield expl substances when nitrated
formaldehyde & w A new two-step synthesis of l,2,4
Ref: Beil 1, 480, ‘[5471 & { 2190) -butanetriol from ally1 ale and formaldehyde is
Nitro-iso-butanediol Dinitrate or 2-Nitro-Z-methyl described in Ref 3
-1,3-propanediol Dinitrate, (O,NO)CH,.C- Refs: l)Bei1 1, 519, [SW] & (2243) 2)Beil
(N02)(CHs).CH2(ON02); mw 225.12, N 18.67%; 1, 519, (276), [ 5961 & { 2344) 3)US Rubber
co1 cfysts, mp 39.5’; Qz 528.2 & QTat 18’ Co, Quarterly Progress Rept No 3, Contract
86.1 kcal/mole(Ref 7); toxic effect is as a NOrd 10129, Passaic, NJ(l948>, 2-9 4)Sax(1957),
vasodilator, less active than NG but shows a 392
more lasting effect(Ref 8); was prepd by nitrating Butanetriol Dinitrate, C,H,N,O,; mw 196.12,
the corresponding alc(Refs 3,4 & 5)(See also N 14.29%. Two isomers are described in the
Ref 2a) literature: 1,2,3-Butanetfiol Dinitrate,
Medard(Ref 6) reported its expl & other CH,.CH(ON02).CH(OH).CH2(ON02); liq expl
props as follows: intermed, obtd by Fichter & Herndl(Ref 2),
Density at Various Pressures: together with other dinitrates, by the electrolysis
Pressure, kg/cm2 of adipates with a Pt electrode in the presence
1.360 2.210 2.720
of NO, ion; and 1,2,&Butanetrio~ Dir&rate,
Density, g/cc 1.58 1.595 1.61
CH2(ON02).CH2.CH(OH).CH2(ON02); Iiq expl
Impact Sensitivity, a 2-kg wt falling from a intermediate,obtd as above(Ref 2)
height of 1;75m produced 60% explns vs 56% Refs: l)Beil-not found Z)F.Fichter & J.HerndI,
 B 371

Helv 25, 229(1942) & CA 36, 5713(1942) 46, 11685(1952) 8)PATR 1740, Revision 1
Butanetriol Trinitrate, C4H7N909, mw 241.12, ( 1958)?PP 37-40 9)W.G.Cl-ke, “Evaluation of
N 17.43%. Two isomers exist: 1,2, 3-Butanetrio~ 1, 2,4-Butanetriol Trinitrate as the Liquid
Trinitrate Or a-Methyl Glycerol Trinitrate, Explosive Plasticizer for Cast Double-Base
CH3 .CH(ON02).CH(ON02 ). CH2(ONOZ); Iiq, Propellant”, PA, FRL Propellant-Res Sec Rpt
d 1.489; S1 sol in w; miscible in ale, eth, acet No 4(1960)(Conf, not used as a source of info)
& 2:1 eth-ale; was prepd by nitrating a-methyl
glycerol(Refs 2, 3 &4). This compd was patented iso-Butanetriol and Derivatives
as a substitute for NG, suitable for mixing iso-Butanetriol, Methyl-propanetriol or
with NG to lower its fr p and was claimed to be Trimethylolmethane, C~kI1 003; mw 160.12.
a powerful expl. Its expl props recorded by Two isomers are described in the literature:
Blatt(Ref 5) are as follows: Impact Sensitivity, Z-Methyl-l, 2,3-propanetriol or /3-M etbylgylceroL
2-kg wt,ca the same as NG(see also M~dard, CH2(OH).C(CH3)(OH), CH2.0H, CO1 vis liq,
Ref 7); Power by Ballistic Mortar Test, ca the bp 115-20° at 1.6mm. d 1.186 at 20°, n~ 1.4730
same strength as NG when used in mizts; at 20° Y can best be prepd by hydration of
Thermal Stability by 82.2° KI Test & ~-methyl-gl ycidol(2,3-epoxy-2-methyl-l-propanol),
Bergmann-Junk Test, ca the same as NG; and and can be prepd direct~y from either
Velocity of Detonation, 7270 m/see. This compd dichloro-tert-butyl alcohol or ~-methylglycerol
and related a-mono & a,a-disubstituted glycerol monochlorohydrin( Ref 2). See also Refs 1,4 & 5);
nitrates have been claimed to be useful expl and 2-(H ydroxym ethyl)-1, 3-propan ediol or
components Trimethylol Methane, CH2(OH).CH(CH20H) ~;
1,2,4-Butanetriol Trinitrate or a,ß,Þ was prepd by Fujii(Ref 3) from a mixt of
-Trihydroxybutane Trinitrate, CH2(ON02).- acetaldehyde & formaldehyde 10:25 mol) heated
CH2.CH(ON02).CH2 (ONOZ), Iiq, d 1.520 at with Ca(OH)2 and the product reduced with H in
20°, n~ 1.4738 at 20°; S1 sol in w; miscible the presence of Ni
with ale, eth, acet & 2:1 eth-aIc; was prepd by The nitrated products of these compds are
nitrating 1,2,4-butanetriol(Ref 6). Due to the expl
fact that this compd is a good gelatinize for Refs: l)Beil 1, 520 2)G.W.Hearne & H.W.
NC, it was used during WWII by the Germans as DeJong, IEC 33, 941(1941) & CA 35, 5858(1941)
substitute for NG in doubIe-base propInts. Its 3)S.Fujii, JapP 153925(1942)& CA 43, 3477
use as a plasticizer for NC was investigated at ( 1949) 4)I.Bergsteinsson, USP 2373942(1945)&
Picatinny Arsenal by Clarke(Ref 9) and at the CA 39, 3006(1945) 5)G.W.Hearne & C.G.
US Naval Powder Factory by Gallaghan(Ref 6). Schwarzer, USP 2600766(1952) & CA 47, 1732
Its expl props were reported in Ref 8 as follows: (1953)
Impact Sensitivity, l-lb wt, ca the same as NG Nitro-iso-butanetriol, Trimethylolnitromethane or
(see also M6dard, Ref 7); Brisance by Sand Test, 2-Nitro-2(hydroxymethyl)-l,3-proponediol(called
ca the same as NG, 49g vs 51.5 for NG; “Nitroisobutylglycerin” in Beil), 02N.C(CHFOH)a;
Explosion Temperature, 5-see value in ‘C, 151.12, N 9.27%; COI ndls or prisms, mp 201
23@vs 22@ for NG; and Thermal Stability by ( 196° for the crude product); Q: 507.8 kcal/mo! rk
Heat, Vacuum Stability and Volati liry Tests,
Q; 173.9 kcal/mol(Ref 2); readily SO1 in w or ale,
more stable than 14G S1 sol in eth; other props & methods of prepn are
Izzo(Ref 4) discussed the expl props in
given in Bed
regard to its use as military or industrial
Re/s: l)Beil 1,520,(276), [5961 & {2345} 2)L.
explosive
M6dsrd & M,Thomas,. MP 35, 158, 172(1953)& CA
Re/s: l)Beil-not found 2)H.P.Groll, USP
49, 11284(1955)
2139364(1938) & CA 33, 2339(1939) 3)N.V.de
Bataafsche Petroleum Maatschappij, FrP Nitro-iso-butanetriol Trinitrate(NIBTN) or
835592( 1938) & CA 33, 4788( 1939) 4)A.Izzo, Nitroisobutylglycerol Trinitrate, also called
ChimIndAgrBiol 16, 155(1940) & CA 34, 4905-6 2-Nitro-2(hydroxymethyl)-1,3-propanediol
(1940) 5)Blatt, OSRD 2014(1944) 6)J.A. Trinitrate or Trimethylolnitromethane
Gallaghan et al, “The Synthesis of 1,2,4 Trinitrate(called “Nitroisobutylglycerintrinitiat”
-Butanetriol and the Evaluation of Its in Beil), 02 N. C(CH2.0NOZ)3, mw 286.12, N
Trinitrate”, “USNavalPowdFactory TechRept NO 19.58%; yel’ viscous oil, fr P ‘39°, d 1.64 at
19(1948) 7)L.M4dard, Mp 31, 143( 1949)& CA 20°, n~ 1. 492 at 20°(Ref 14) and 1.4896 at
 B 372

25°(Ref 16); Q: 530.5 kcal/mol & Q? 50.0 Explosives Derived from Nitroparaffins”, PATR
kcal/mol(Ref 12); volatility lower than for NG, 1125, (1941) 9)Blatt, OSRD 201 4(1944)
namely, at 25° 0.127 x 10-3 g/cm2/24 hrs vs (Trimethylolnitromethane .Trinitrate) 10)
0.153 x 10-3 for NG. NIBTN is sol in methyl & Stettbacher(1948), 69 ll)L.M~datd, MP 31,
ethyl alcohols, acet, ether, ethylene dichloride, 143(1949) & CA 46, 11685(1952) 12)L.M&dard &
chlf & benz; insol in w, ~z & petr eth; toxicity M.Thomas, MP 31, 196(1949) & CA 46, 11684
much lower than with NG; It causes only a (1952) 13)J .Tranchant,’ MP 32, 313-18(1950)&
slight headache; its gelatinizing action on CA 47, 9014(1953) 14)J .Boileau & M. Thomas,
collodion cotton is appreciably less than that of MP 33, 155-7(1951) &CA 47, 5201(1953) 15)
NG, even when hot Stettbacher( 1952), 94 16)PATR 1740, Revision
NIBTN was first prepd by Hofwimmer(Refs 1(1958),PP 223-5
1 & 2) by condensation of 3 moles of formaldehyde
with 1 mole nitromethane in the presence of Nitro-iso-butanetriol Triacetate or 2-Nitro-2
KHC03 and subsequent nitration of the product. -(hydroxymethyl).l,3-propanediol Triacetate,
Modifications of this method are described in 02 NC(CH200C.CH3)3, was patented in Italy
Refs 3,4,5,6,10 & 15. Aaronson(Ref 8) investi- as an ingredient of blasting expl: RDX(or PETN)
gated the methods existing prior to 1941 and came 75 & nitro-iso-butanetriol triacetate 25%, melted
to the conclusion that ‘Stettbacher’s method(Ref together at 80°
5) was the best Ref: “Montecantini” Societ~ Generale per
The exp, props of NIB TN, recorded by L’indusrria Mineraria e Chimica, ItalP 433633
Stettbacher(Ref 5), Blatt(Ref 9), PicArsnTech- (1948) &CA 44, 1709(1950)
Repts(Refs 8 & 16) and by M~dard(Ref 12), are
as follows: Bn”sarzce, by Sand Test, 56g vs 52g Butanoic Acid. Same as Butyric Acid
for NG, using kieselguhr as absorbent(Ref 16);
Detonation Rate, 7860 m/see at d 1.6o vs 7700 at Butanol and Derivatives
d 1.6 for NG(Ref 16); Explosion Temperature, Butanol or Butyl Alcohol(called Butanol or
185 °(ignited) vs 222°(expl) for NG(5 see); lrnpuct Butylalkohol in Ger), C4Ht ~O; mw 74.12. Four
Sensitivity: Nao~m(Ref 3,p 241) gave 6cm vs isomers are known: n- or B utan-1-ol,
2cm for NG(Kast app, 2-kg wt); Aaronson(Ref 8) CH3(CH2)2CH2.0H, CO1 Iiq, fr p -89°,-bp
- 25cm vs 44cm for NG(BM app, 2-kg wt); later, 117.7°, d 0.8109 at 20°, fl p 114°F(TOC)(Ref 1;
PicArsn value for NG was given as 15cm(Ref 16) Ref 6,P 396 & Ref 7,P 182); see- or Butan-2-oL
and M~dard’s tests showed that NIBTN is less CH3.CH2CH(OH).CH3, CO1 liq, fr p -114.7°,
sensitive than NG(Ref 12); Power, by Trauzl bp 99.5°, d 0.808 at 20°, fl p 75°F(CC)(Ref 2;
Test, for a mixt with 75% kieselguhr 325cc vs Ref 6,p 396 & Ref 7,p 182); iso-Butunol,
305cc for a similar NG mixt; for the mixt (CH )2CH.CH2.0H, clear Iiq, fr p -108°, bp
NIBTN/NC-93/7580cc vs 600cc for a similar 107F, d 0.805 at 20°, fl p 82° -lOO°F(COC)
NG mixt(Blasting Gelatin)(Ref 3); Thermal (Ref 3; Ref 6,P 793 & Ref 7,p 622); and
.$tabili ty. Nao6tn(Ref 3) reported its stability at #ert-Butanol, (CH3)3C.0H, low-melting CO1
70-80° to be not less than that of NG, but in trysts or liq having the odor of camphor, mp
Ref 16, its stability by the 82.2° KI test is 25,3°, bp 83°, d 0.78 at 20°, fl p 52°F(CC)
2mins vs lot for NG (Ref 4; Ref 6,p 397 & Ref 7,p 183). These
Tranchant(Ref 13) studied the props of alcohols are of mod toxicity and they represent
NIBTN and incorporated it in double-base expln hazards in the following concns in air:
proplnts by substituting for NG; Bronstein(Ref 7) n- 1.7 to 18%; see- unkown; iso- 1.9 to 8.5% and
patented an expl consisting of NIBTN 25-75 & tert- 2.4 to 8.0~.(Ref 6). Butanols are used as
NS 75-25% together with coating agents solvents for resins & coatings and as inter-
ZZe/s: l)Beil 1, (277), & { 2346} 2)F.Hofwimmer, mediates in org synthesis. According to
ss 7, 43(1912) & CA 6, 1228(1912) 3)Nao~m, Tavemier(Ref 5), butanol was used a a SOIV in
NG(1928), 239-41 4)(?)Aubry, MP 25, 197-204 the prepn of some French proplnts
(1932-33) & CA 27, 4083(1933) 5) AStettbacher> Refs: l)Beil 1, 367, (186), [ 387] & { 1480}
NC 5, 159-62, 181-4 & 203-6(1934) 6)G.A. 2)Beil 1, 371, 373, (188, 189), [400,404,405]
Hunold, SS 30, 263-4(1935) & CA 2978333 & { 1527} 3)Beil 1, 373, (189), [405] & {1550}
(1935) 7)] .B.Bronstein, Jr, Usp 2170629(1939) 4)Beil 1, 379, (192), [413] & {1568} s)P.
& CA 34, 266(1940) 8)H.A.Aaronson, “Study of Tavemier, MP 38, 309(1956) 6)Sax(1957), 396,

——_l_– —.-——. -.
 B 373

397 & 793 7)CondChemDict( 1961), 182,183 & d 0.876 at 26°, vap d 3.5(Refs 1 & 7); sec
622 8)US Spec TT-B-00846A & TT-B-846(1) -Butyl Nitrite, CH3.CH2-CH(ONO)CHg, Iiq,
(n-Butanol for use in org coatings) 9)US Spec bp 68°, d 0.898 at 0°, vap d 3.5(Refs 2 & 7);
TT-B-848B(sec-Butanol for use in org coatings) iso-Butyl Nitrite (CH ) CH.CHZ(ONO), Iiq, bp
IO)US Spec TT-I-730(iso-butsnol fcir use in org 67.1°, d 0.865 at 25°~ ~~ 1.3715 at 22. 1°(Ref 3);
coatings) and tert-Brftyl Nitrite, (CH~)3~ONO), yel Iiq,
Butanol Nitrate or Butyl Nitrate, C4~N()~; mw
bp 68°, d 0,894 at O0, vap d 3,5(Refs 4 & 7).
119.12, N 11. 76%. Four isomers are known: rz-Butyl
Other props & methods of prepn tie given in the
Nitrate, CH,(CH,)2CH,(ON0,), CO1liq, bp 136°, .fl P
Refs. Butyl nitrite is a fuel & is the most
97°F, d 1.03 at 20°(Refs 1,5 & 6); sec-Buiyl ignitable of the fuels examined by Mullins(Ref 6)
Nitrate, CH .CH2 .CH(ON02), liq, bp 124°,
Re/s: l)BeiI 1, 369, [397] & {1509}. 2)Beil
d 1.038 at O%, vap d 4. O(Refs 2 & 5); iso-Bzityl
1, 372& [402,404,405] 3)Beil 1, 377, (190),
Nitrate, (CHa)zCH.CHz(ONC)2), Iiq, bp 123°,
[411] &’{1562} 4)Beil 1, 382, [415] &
d 1.017 at 20°(Ref 3); and tert-Butyl Nitrate,
{1582} 5)W.A.Noyes, OrgSynthCOllVO12
(cH~)3.C(0N02j, Iiq, bp 21-2° at 4-5mm, d ( 1943),pp 108-9(Prepn of butyl nitrite) 6)B.p.
1.015 at 20°(Refs 4 & 4a). These compds are Mullins, Fuel 32, 451-66( 1953) & CA 47,
formed by adding HN03 to the corresponding 12785-6(1953) 7)Sax(1957), 409
ales. They are non-expl but form other derivs
Nitrobutanol Nitrite or Nitrobutyl Nitrite, C,H,N,O,;
which are expl
mw 148.12, N 18.91%. Two isomers are described
Re/s: l)Beil 1, 369, [397] & { 1509] 2)Beil
in the literature 4- Nitro- l-butyl Nitn”te,
1, 372, (188) 3)Beil 1, 377, [411~ & { 1562} 02 N. CH2(CH2)2CH2(ONO), liq, bp 110° at 14mm
4)Beil 1, { 1582} 4a) A. Michael & G. H. Carlson,
(dec)(Refs 1 & 2); and Nitro-tert-butyl Nitrite or
JACS 57, 1271(1935)& CA 29, 5811(1935) 1 -NitIv-2-metb yl.2.prop yl Nitrite,
5)Sax(1957), 408-9 6)CondChemDict( 1961), 188
(CH9)2C(9N0)CHz.N02, oily liq, fr p 24.5-25.5°,
Nitrobutanol Nitrate or Nitrobutyl Nitrate, bp 82-3° at lmm, d 1.302 at 25°, no 1.4599 at
C4H~N20~; mw 164.12, N 17. 07%. Several isomers are 25°(Ref 3). Other props & methods of prepn are
known: 2-Nitro- I-butyl Nit@e, W ‘CHZoCH(NOZ)”- given in the Refs
CH,(ON02), liq, d 1.242 at 15.51Ref 1X 2-Nitro-3 R e/s: l)Beil 1, (187) 2) J.vonBraun & W.
-butyl-nitrate, CHS”CH(ONOZ).CH(NOZ) OCHS,no Sobecki, Ber 44, 2528(1911) & JCS 100 I, 830
props given (Ref 3); Nitro-iso-but yl Nitrate, (1911) 3)C.C.Price & C.A.Sears, JACS 75,
0zN.CH~,CH(CH3) .CH2(ONOz), was used as a 3276(1953) & CA 49, 6153(1955)
sensitizer, together with AN & other substances,
to form a safety expl(Ref 3); and Nitro-tert-butyl
Nitrate or 1-Nitro=2-metby l=2-pmpyl Nitrate.
Mononitrobutanol, CaHQNOa; mw 119.12, N
(CH3) C(ON02).CH2.N02, liq, bp 78° at lmm,
11.76%. The folIow[ng-are-among the known
fr p ($, d 1.283 at 20°, n~ 1.449 at 20°(Refs
isomers: 2-Nitrobutan-l-oI, CH3 .CH2 .CH(N02).-
la,3,4,5,6,7 & “8); cm be. used as a monofuel in
C3i2.0H, liq, fr p -47°, bp 127-30° at 35mm, d
the presence of a cat~yst(Ref 7)$ the IR
1.137 at 11.5°(Refs 1 & 7); 4-Nitrobutan=2-oL
spectra of these compds are given in Brown(Ref 8)
O N(CH2)40H, liq, bp 103° at 2mm, d 1.112 at
Re/s: l)Beil 1, 370 la)Beil 1, { 1588} 2)R.F.B.
20%(Ref 6); l-Nitrobutan-2-ol, CH .CH2.CH(OH).-
COX, USP 2330112(1943)& CA 38, 1368(1944)
CH2 ,N02, viscous liq, bp 123-253 at 35mm(dec),
3)A.E.Wilder-Smith et al, Brirp 580260(1946) ~
d I. 191 at 18°(Ref 2); 3-Nitrobutan-2-oz,
CA 41, 2069(1947) 4)A.E.Wilder-Smith et ~,
CH3 .CH(NOZ).CH(OH).CH3, liq, bp 112-13° at
BritP 586022(1947)& CA 41, 6893(1947) 5)N*
38mm, d 1.116 at 7.8°(Ref 3X @Vitro-iso
Levy et al, JCS 1948153,57 & CA 42> 4906(1948)
- butanol or 2-Nitro-2-methy l-1-p mpatrol,
6) A. E.Wilder-Smith et al, USP 2453942(1948)&
(CH3)8C(NOZ)CH2 .0H, ndls or lfts(from MeOH),
CA 43, 5411(1949) 7)A.C.Hutch~sont ‘tThe USe
mp 82 (Ref 4); and Nitro-tert-butanol,
of Alkyl Nitrates as Liquid Monofuels”, ICIL,
Nobel Div( 1950),p 8 8)J.F.Brown, Jr, JACS (CH3)ZC(OH)CH2.NO%, ndls, mp 26°, bp (!@
at lmm, d 1.132 at 20 (Refs 5 & 5a). Other
77, 6341-51(1955) & CA 50, 2297(1956)
props & methods of pre n are given in the Refs
Butanol Nitrite or Butyl Nitrite, C,~NO,; mw 103.12, Refs: l)Beil 1, 370 & ! 1519} 2)Beil 1, 373,
N 13. 58%. The following isomers are known: rz-qutyl [403] & { 1546} 3)Beil 1, 373 & { 547} 4)Beil
Nitrr”te CH3(CH2)2CH2)ONO), liq, bp 77.8°, 1, 378 & { 1564} 5)Beil 1, { 1588} 5a)N.Levy
 I

B 374

et al, JCS 1948, 53, 57 & CA 42, 4906(1948) Butanolaniline. See Anilinobutanol; Vol l,p
6)H.Shechter et al, JACS 74, 3667(1952) & CA A422-R
47, 5886( 1953) 7)Ss2(1957, 946
Dinitrobutanol, C4H~N20g; rnw 164.12, N 17.07%. Butanone and Derivatives
Several isomers are known: 2,2-Dinitmbutan-t-ol, Butanone or Metbylethylketone( called Butanon or
CH3.CH2C(N02)2 .CH2.0H, pale-yel Iiq, fr p -5°; Methyl?ithylketon in Ger), CH3.CH2.C0.CH3;
was prepd by reaction of an aq soln of the K salt mw 72.10, 0 22.9%; CO1, flammable liq having
of 1, l-dinitropropane & formaldehyde. It is a acetone-like odor, fr p -86°, bp 79°, flash p
powerful expl having the following props(Ref 3): 22°F(TOC), d 0.8062 at 20°, vap d 2.41, vap
Ex#tlosion Temperature, does not expl up to press 71.2mm at 20°, nu 1.379 at 20°; sol in
360°; Hygroscopicity at 25°, gains 008r0 at ale, eth or w & miscible with oils. Sax(Ref 4)
100%RH; Impact Sensitivity, ca the same as lists its MAC as 250 ppm or 735mg/m3 in air
TNT; Power by Ballistic Mortar Test 94%TNT, and its expl range 1.81 to 11.5%. Smith &
using a Tetryl booster; Reactivity, cleaved to Mayers(Ref 2) reported that acute poisoning was
1,1-dinitropropane & HCHO by K2C03; and produced from a combination of acetone &
Stability by 13.5° Heat Test, acid in 30min, no butanone vapors in a concn of 1000 ppm. Low
expl in 300min & by 75 °1ntemational Test, looses -grade intoxication & dermatirus were caused by
1.6$z; and 1, l-Dirzitrobutan-2-ol, CH3 .CH2 .CH(OH) butanone alone in concns of 300-600 ppm. Prepn
CH(N02)2, oily liq, diffc sol in w; was prepd by & other props of butanone are given in the
the action of the K salt of dinitromethane & Refs, It is used as a solvent, in org synthesis
propionaIdehyde in water. Its K salt, & in the manuf of smokeless proplnts
K. C4H7N20g, yel lfts, explodes ca 205 °(Ref lk R e~s: l)Beil 1, 666, (347), [726] & { 2770}
3, 3-Dirzitrobutan.2-ol, CH3 .CH2 .C(N02)2.CH(OH).- 2)A.E.Smith & M. R. Mayers, IndBull(NY State
CH~, described in Conf Ref 5; 1, l- Dirzitro-butan Dept of Labor) 23, 174-6(1944) & CA 38, 5613
-3-o1, CH3.CH(OH).CH2. CH(N02)2, a new ( 1944) 3)Shell Chemical Corp, “Methyl Ethyl
compd, prepn & proof of structure to be published Ketone”, NY(195o), 129pp [Reviewed in
(Ref 6); and 1,3-Dinitro-tert-butaol or 1,3 JChemEd 27, 696(1950)] 4)Sax(1957), 392
.Dinitm.2-metbylpmp@-2-ol, 02 N.CH2 .C(CH3 )- 5)Faith, Keyes& Clark(1957), 517-19 6) Cond-
(OH). CH2.N02, COI trysts, mp 310, fr p 108° at ChemDict( 1961), 739
< lmm; was prepd by reaction of 3-nitro-2-methyl Azidobutanone or Butanone Azide, C4H7N30;
-1-propylene with N204 in eth at -10° and mw 113.12, N 37,15%. Two isomers are known:
treating the reaction product with water(Refs 2& l-Azidobutan-2-one, CH3 .CH2.C0,CH2.N3, COI
4). The IR spectra of various nitro & other oil, bp 56° at 2mm, d 1.084 at 18°; ignites with
oxidized nitro compds are given by Brown(Ref 6). a feeble deton when thrown on a hot plate; was
The dinitro compds of butanol are ezpl prepd by treating l-chlorobutan-2-one with aq
Re/s: l)Beil 1, 373 2)Beil 1, { 1589} 3) Blatt, NsN3 contg a Iittle acetic acid(Refs 1 & 2,p
OSRD 2014(1944) 4)N.Levy et al, JCS 1948, 58 677); and 3-Azidobutan-2-one, CH3 .CH(N3).C0.-
& CA 42, 4906(1948) 5) Aerojet Rept 331( 1948),pp CH3, coltoil, bp 46° at 2mm, d 1.057; vaporizes
69 & 143( Confidential) 6)J.F.Brown, Jr, JACS w/o ign or deton when dropped on a hot plate;
~, 6342-45( 1955)& CA 50, 2297( 1956) was prepd from l-chlorobtitan-2-one, aq NaN3 &
l,l,l-Trinitrobutanol, H3C.CH2.CH(OH).C- a little acetic acid(Refs 1 & 2,p 675)
(N02)2. The prepn of this compd from Refs: l)Beil 1, 671 2)M.O.Forster & H.E.
propionaldehyde & nitroform was reported in Fierz, JCS 93 I, 675 & 677(1908)
3-Diazobutan-2-one, CH3 .C(:N;N).C0.CH3;
Ref 2. Later it found(Ref 3), that the compd was
mw 98.1o, N 28.56%; dk-om Iiq having a
actually methyl-l, 1, l-tn”nitro-2-butyl ether,
H3C.CH2.$H.0.CH3 stupefying ethereal odor, bp 45° at 12mm; the
olive-gin vapor explodes violently when air is
C(N02)9
admitted too quickly to the distilling flask; was
Refs: l) Beil-not found 2)US Rubber Co
Quarterly Progress Rept No 2, Contract Nerd prepd by treating diacetyl monohydrazone in abs
10129, Passaic, NJ(1948-49), 17-18 3)Ibid, eth with silver oxide & sodium sulfate; it evolves
Rept No 9(1949-50), 7-8 N when treated with w, alc or acids(Refs I & 2).
See also Ref 3
1. Butanol-2-amine. See 2-Amino- l-butanol; Re/s.’ l)Beil ~, (399) 2)0. DieIs & K.P flaumer,
Vol l,p A 192-L Ber 48, 229(1915) & JCS 108 I, 128(1915) 3)B.
 B 375

Prijs et al, HeIv 30, 2112(1947)& CA 42, 1934 91( 1907); CA 1, 1121(1907)& JCS 92 I, 185(1907)
(1948) 3)CondChemDict( 1961),p 683
Mononitrobutonone, C4H7NO~; mw 117.10, N
11.96%. Two isomers are described in the Butene and Derivatives
literature: 1.Nitrobukm-2.one, CH$.CHz.CO.- Butene or Butylene(called Buten or Butylen in
CH2.N02, liq, fr p 12-15°, bp 92-100° at Ger), C4H@, mw 56.10. Four isomers exist:
8mm & 118° at 28mm, d 1.156 at 20°, n~ 1.4410 1- or a- Butene, CH2 :CH.CH2.CH3, gas, fr p
at 20°; and 3-Nitrobutan-2-one, CH3.CH(N02).- -185°, bp -6.3, flash p -80°, d 0.5951 at 20°,
CO.CH~, CO1 liq, fr p- failed to solidify in vap d l,93(Ref 1; 4,p 404 & 5,p 179); cis-2 or
ice-salt, bp 71-5° at 9mm & 92° at 25mm, d pButene, CH, ,CH:CH.CH,, gas, fr p -139°,
1.156 at 20°, n~ 1.4349 at 20°. These nitro- bp 3.7°, flash p -73°, d 0.6213 at 200, vap press
ketones were synthesized by oxidn of the 1410mm at 21°(Ref 2; Ref 4,p 393 & Ref 5,p
corresponding alcohols. The nittobutanones 180); truns-2 or @Buterte, gas, fr p -105.8°,
must be distilled at reduced pressure, with air bp 0.9°, flash p -73°, d 0.6042 at 20°, vap press
excluded, in order to prevent violent decompn. i592m-m at 21°(Refs 2; Ref 4,p 393 & Ref 5,p
The Na salts as well as the bromo derivs of 180); and iso-Buterze, iso-Butylene or 2
these nitrobutanones were prepd -Metbylpropene, (CH~) C:CH2, vol liq or easily
Re/s: l)Beil-not found 2)C.D.Hurd & M.E. Iiquified gas, fr p -139$, bp -6.9°, flash p -76°, d
Neilson, JOC 20, 932(1955)& CA 50, 6310(1956) 0.600 at 20°, vap press 3290mm at 40.5°(Ref 3;
Butonone Azide. See Azidobutanone Ref 4,p 795 & Ref 5,p 621). The toxicity
details of these compds are unknown but they
Butanoneoxime and Derivatives act as anesthetic or asphyxiant(Ref 4). Prepn
Butanoneoxime [called Butanoxim-( 2) or & other props of these compds are given in
Methyliithylketoxim in Ger] , CH3 .CH2.C- Beil(Refs 1,2 & 3). They are used as SOIVS, in
(:NOH).CHa; mw 87.12, N 16.08%; CO1 oil, org synthesis as intermediates &as starting
fr p -29.5°, bp 151-2°, d 0.9232 at 20°, no materials for liq fuels(Ref 4)
I.441O at 200. Other props & methods of prepn Note: When 5g of iso-butylene was treated with
are given in the Ref 1.9g of nitroform in 7ml of ether(as described in
Re/: Beil 1, 668, (348), [730] & { 2784} Ref 3a), there was obtained 1.2g of liquid which
l-Azidohutarzorz e-2-oxime, CH~.CH2.C(:N.0H).- could not be purified by distillation even at
CHZ.N3: mw 128.14, N 43.73%; liq, obtd by 1 micron pressure. Its probable compn was:
treating l-azidobutan-2-one with aq h ydroxylamine; 2 [(CH3)2C:CH2 ] + HC(N02)~. An attempt to
decompd by warming with dil alk & yielded HN~ prep a larger quantity resulted in a violent
when acidified(Refs 1 & 2) expln. This reaction has not been investigated
The p-Toluenesu~fonyl deriv, further
Cl, H, ~Na03S, CO1 ndls(from petr), mp 72°, obtd Re/s: l)Beil 1, 203, (84) & [ 173] 2)Beil 1,
by mixing the oxime in pyridine soln with the 204, (85) & [ 175] 3)Beil 1, (85) & [ 179]
calcd quantity of p-toluenesulfonyl chloride,. 3a)US Rubber Co, Quarterly Progress Rept N5,
exploded when heated at or above its mp(Ref 2) Contract Nerd 10129, Passaic, NJ (1949-50), 10
Re/s: l)Beil 1, 671 2)M.0. Forster & H.E. 4)Sax( 1957), 393, 404 & 795 5)CondChemDict
Fierz, JCS 93 I, 678(1908) (1961), 179, 180 & 621
Butanone Peroxide Dimer, Methylethylketone Mononitrobutene, C4H7N02; mw 101.10, N
Peroxide, (C4H@Oz)2; mw 176.21, 0 36.20%; COI 13.86%. The following isomers are known:
thick oil, having a pleasant odoq stable at RT l’-Nitro-l-butene, CH3.CH2.CH:CH.N02, yel
but explodes when heated above 100 0, d 1.042; Iiq having a pungent odor, bp 55° at 12mm, d
was obtd when butanone was treated with HZC)2 1.025 at 20°, n~ 1.4532 at 20 °(Refs 2 & 3);
in the presence of HzSO,; sol in ale, eth or benz; 2-Nitro-l-bufene, CH3 .CH2C (N02):CH2, liq,
insol in w._ The compd is completely reduced to bp 60.5° at 50mm(Refs 4 & 8), volatility & vap
methyl eth ylketon e by the action of nascent H in press are given by Redemann et aI(Ref 6); during
the cold; it explodes violently when placed in the prepn of polynitro paraffins, Bshner & Kite
contact with coned H2S04. Butanone peroxide (Ref 7) found that metallic Na added to an
is sold under the trade name ‘* Lupersol DDM”, equi-molar mixt of (CH3 )2 CH.N02 & 2-nitro- 1
by Wallace & Tiernen, Inc, Buffalo, NY(Ref 3) -butene at 8° caused a violent reaction & mild
Re/s: l)Beil 1, 668 2)J.Pastureau, CR 144, ex.pin; l-Nitro-2-buten e(trans), CH3 .CH:CH.-
 B 376

CH2N02(Ref 9); 2-Nitro-2-buterze, CH3 .CH:C- pp 68 & 143

(N02).CH3, bp 58° at 18mm & 70.4° at 30mm,
d 1.043 at 25°, n~ 1.4584 at 25 °(Refs 5 & 8); Butene Polymer Dynamite. A cohesive,
a-Nitro-iso-butene or 1 -iVitro-2-methyl-l -propene, nonsifting Dynamite was prepd from NG 6, AN
(CH3)2C:CH.N02, It yel oil having a disagreeable 80.4, NsN03 5, woodpulp 2, fine apricot-pit
odor, bp 154-8 °(partial decompn), d 1.052 at 0° pulp 4.1, yel com flour 1.5, chalk 0.5 & 0.5% of
(Refs 1) andl-Nitm-2-methyl-2-pm#J ene or 3 a soln contg 7.5% polybutene(solid rubber of mw
-Nitro-2-methyl-l -pmpene, CH, :C(CHa).CH2.N02, 80,000) in Iiq polybutene(viscosity 154 Saybolt
props not given(Ref 9). The IR spectra of the Universal seconds at 210 °F)(Ref). Other
above compds, except 2-nitro-~-butene & 2-nitro formulations of powdery cohesive Dynamites
-2-butene, are given by Brown, Jr(Ref 9). are also given
Methods of prepn & other props are given in the Re/: W.J.Taylor, USP 2541389(1951) & CA 45,
Refs 4930(1951)
Re/s: l)Beil 1, 209 2)Beil 1, 1175] 3)E.
Schmidt & G. Rutz, Ber 61, 2147(1928) & CA 23, Butenoic Acid. Same as Crotonic Acid
372(1929) 4)Visking COrP, Britp 593109(1947)&
CA 44, 653(1950) 5)N.Levy et al, JC.S 1948, Butenyl. The monovalent radical C4H7- derived
5260 & CA 42, 4906(1948) 6) C. E. Redemann et al, from butylene or butene
JACS 70, 2582(1948)& CA 42, 8563(1948)
7)C.T.Bahner & H.T,Kite, JACS 71, 3597-8 Butine or Butyne. An unsaturated hydrocarbon
( 1949)& CA 44, 1010(1950) 8)H.B.Haas et aI, contg a triple bond
JOC 15, 8(1950)&CA 44, 4412(1950) 9)J.F.
Brown, JrZ JACS 77, 6342(1955) & CA 50, Butlerov, Alexander M.(1828- ISS6). Russian
2297(1956) chemist known for his numerous works in organic
Dinitrobutene, C4H6N204; mw 146.10, N 19.18%. chemistry. He discovered formaldehyde in 1859
The following isomers exist: 3,3-DinifYo-l and studied its reactions with ammonia, including
-butetze, CHa.C(N02)2.CH:CH , liq, bp 59.0 the formation of hexamethylenetetrmine
-59.5° at 4.5mm, d 1.248 at 20S, n~ 1.4535 at Re/s: l)H.M.Leicester, JchemEduc 17, 203.9
200; was prepd from 3,3-dinitro-l-bromobutane ~ ( 1940) 2)Walker, Formaldehyde(1953), 2
NaOMe in methyl alcohol(Ref 4); ~, 4- Dinitro-2
-butene, 02 N. CH2.CH:CH.CH2.NOZ, yel oil , bp Butterfly Bombs. See Bombs, Butterfly under
58-60( dec); was prepd by the action of Noz or List of Bombs
N20~ on butadiene(Refs 2 & 5); was proposed
as an insecticide & as a solvent for NC(Ref 2; Butterfly Valve. See under Cartridge Actuated
and 2, 3-Llinitro-2-butene, Cl-Ia .C(N02):C(N02).- Devices
CH3, pale yel liq, fr p 28-9°, bp 96-8° at lmm
(sublimes at 20° & 10-4 mm); IR spectra Butt Target. A mound, bank or other backstop
indicate trans form(Ref 6); was prepd by the of earth that catches bullets & projectiles from
action of N204 on butync~2(CH3 .C;C. CH3) in artillery or rifles used in target practice or
acet under cooling(Ref 6); was considered suit- proving ground tests
able as an ign improving agent in diesel fuels & Ref: Merriam-Webster)s( 1961), 304
as an intermed in_org synthesis(Ref 3)
Refs: 1 )Beil-not found 2)R.G.Franklin & F.]. iso-Butyl Acetyl Ricinoleate(called Acetat des
Wilkins, USP 2314615(1943) & CA 37, 5188 Ricinolsiiureisobutylesters in Ger), C24H440,
(1943) 3)E.M.Nyga$rd & T, T. Noland, USP mw 396.59; non-vol liq, bp 255-600 at 13mm,
2396282(1946) & CA 40, 3126(1946) 4)Ho d 0.9012 at 22°, n~ 1.4548 at 22°; was prepd
Shechter & L.Zeldin, JACS 73, 1276(1951) & CA from iso-butyl ricinoleate and acetyl chloride at
45, 9458-9(1951) 5)C.R.Porter & B.Wood, 60-80°(Ref 1)
JInstPetroleum 38, 877(1952)& CA 47, 10457 This non-expl compd was proposed as a
(1953) 6)H.H.Schlubach & W.Rott, Ann 594, surface geIatinizer for double-base proplnts used
59-66(1955) & CA 50, 10666(1956) at sub-zero temps(Ref 2). It is a non-solv for
Trinitrobutene, C4H~N306; mw 191,10, N 21.99%. NC, but is compatible in a mixt contg NC, NG,
The 4, 4,4- Trinitro-l-butene, (02 N)3C.CH2.CH:- rosin & a solv(such as o-benzoylbenzoate) for NC;
CH2, is described in Conf Aerojet Rpt 331 (1948), and may be suitable, therefore, as an ingredient

——
 B 377

of certain proplnts Hickinbottom, JCS 111, 1034(1917)

Re/s: l)Beil 3, 388 2)E.S.Goodyear, US!?
2179330(1939) & CA 34, 1488( 1940) Butylaminoethanol. Same as Butylethanolamine

Butyl Alcohol. See Butanol Butylaminomethylbenzene, Same as

C-Butylaminotoluene
Butylomine and Derivatives
Butylamine or Amirzobutune, C4H9NH2. Several C-Butyl-aminotoluene
isomers are known and described in Beil 4,156, and Derivatives
160,161,173,(370,372,376) & [631,636 & 641] C-Butyl-amiaotoluene, C-ButyLmetby~arziline or
Butylnitramine, C4HI ON202; mw 118.14, N C-Butylarninometbylbenzene(called
23. 71%. Three isomers are described in the Aminomethylbutylbenzol in Beil), C4H9.CsH3-
literature: n-Butylnitrarnine, C4H9.NH.N02, liq, (NH,).CH,. Six isomers are described in Beil
fr p -1 to 0°, bp 123-5° at 20mm, d 1.058 at 12, 1180 & [643,645]
23°, n~ 1.4603 ,at 25°; forms several tryst salts Nitro-C-butyLamirzotoluene, C4H~.C6H2(N02)-
(Ref 1 & 2), Smart & Wright(Ref 3) prepd the (NH2).CH,. One isomer is described in Beil
compd by nitration of n-but yldi chloramine( 1 mol) 12, 1181
in acetic anhydride(5 mols) with 98% HNOg Dinitro-C-butyl-aminotoluene, C4H~.CeH(N02)2-
(3 mols). When the nitration was attempted in 10 (NH2).CH30 One isomer is described in Beil
equivalents of HN03 and w/o acetic anhydride, 12, 1181
the reaction mixt survived at-35° but decompd Trinitro-C-butyl.aminotaluene, C, , H, ~N40G,
explosively when warmed to -200; sec mw 298.25, N 18.79%. One isomer, 3,5,6
-Butylnitramine, C2H~.CH(CH3 ). NH.N02, Iiq, -Trinitro-4-(tert- butyl)-l -amino-tolu ene or
fr p -32.5°, bp 106.2-106.7° at 15mm, d 1.057 3,5, 6- Tn”nitro-4-(tert-butyl)-2-methyl-anilive,
at 22°, no 1.4572 at 25 °(Refs 1 & 2). Smart & [called 2.4.5-Trinitro-6-amino- l-methyl-3-(tert
Wright(Ref 3) prepd the compd by nitration of -butyl)-bmzol in Ger] , C4H9 .C6(N0 ~) -
83
sec-butyldichloramine in SI more that equiv amts (NH2).CH~, crysts(from ale), mp 168 ; was
of acet anhyd & HNO~. The intermediate compd, prepd by di azotizing an alc soln of 5-nitro-4
see-But yl-N-chloronitramine could not be -(t ert-but yl)-1-amino-toluene, follo wed by distn
isolated because of its expl nature; but a compd with steam. Energetic nitration of the trinitro
believed to be sec-Butylnitramine, C2H~.- deriv yielded an acid expi product; yel ndls(from
C(CH3 ):N.N02, was isolated; iso-Butylrzitrarnine, ale), mp 224° of assumed formula, C6(N02 )5. NH.-
(CH3)2.CH.CH2.NH.N02, tryst, mp 32,2°, d NO
1.142 at 15°; fo~s cysts salts(Ref 1); Re/s: l)Beil 12, 1181 2)A.Baur, Ber 30, 304-5
other props & method of prepn are given in Ref 2 ( 1897)& JCS 72 I, 216(1897)
Re/.s: l)Beil 4; 571(569) 2)H.Vsn Erp, Rec
14,26,31,32(1895) 3)G.N.R.Sm~ & G. F. Wright, N-Butyl-aminotoluene
CanJRes 26 B,290,291(1948) & CA 42, 5844 and Derivatives
(1948) N-ButyLaminotoluene; N-Butyl-metbylaniline;
N-Brityl-toluidine, C4H9.HN.C6H4 .CH3. Four
Butylaminobenzene. same as Butylaniline isomers are described in Beil 12, (377,414) &
[436,492]
1-Butylaminobenzene-4-diazonium Hydroxide, Nitro-N-butylaminotoluen e, C4Hg.NH.C6H3(N02)-
C4H9.NH,C6H4.N( ;N).0H; mw 193.24, N 21.75%; CH3. Three isomers are described in Beil 12,
known only in the form of its salts, some of (438, 440)
which are expl; P latirzic Chloride salt, 3, 5-Dinitro-4=N-butyl-aminotoIuene, C4H9.HN.-
(Cl oHb4N.N2.C0 * + PtC14, yel ppt, turns dark at C6H2(N02)2.CH3; mw 253.25, N 16.59%; em-red
115-20 , dec at 147-50° and explodes on heating ndls, mp 53-4°, is described in Beil 12,(443)
in a flame; sl sol in sic, almost insol in w, 3, ~-Dinittu-4-(N.butyl-N. nitroso)-aminotoluene,
was prepd by treating a soln of platinic chloride C4H9.N(NO).C6H2 (N02)2.CH3; mw 282.25, N
with the diazotized aq soln of butylaminodiazonium 19.85%, It yel plates, mp 56-7°, is described in
dihydtochloride, which was obtd by reacting Beil 12,(444)
N-butylphenylene diamine with NaN02 & HCI 3,5-Dinitro-4-( N- butyl-N-nitro)-aminotoluene,
Re/s: l)Beil 16, (371) 2) J.Reilly & W.J, C4H9.N(N02).C6H2 (N02)2.CH3, mw 298.25,
 B 378

N 18.97%, yel ndls, mp 95°, is described in N-Butylaniline, N-Butylaminobenzene or

Beil 12, (444) Phenylbutylamine( called Butylanilin in Ger),
2,3,5-Trinitro-4-(N-butyl-N-nitroso)-aminotoluene, CIOH1 ~N, mw 149.23, N 9.39%. Four isomers
C4H9.N(NO).C6H(N02 )9.CHa, mw 327.25, N exist and are described in the literature:
21.40%, yel crysts(from dil ale), mp 80.5°. Can n- f?utylaniline, CH .(CH2 )3 .NH.CGH~, CO1 k
be prepd by treating(at 30-35° for 2 hrs) fr p -15.1°, bp 241?, flash p 225 °F(COC)(Refs
2-nitro-N-butylaminotoluene sulfate with a mixt 1, 4 & 5); sec-B~tyZaniZine, C2H5 lCH(CH3 )0-
of HN03(d 1.4) ~d coned H2S04. Its expl NH.C6H ; aromatic oil, having pleasant odor,
props were not investigated bp 224-5S at 765mm(Ref 3); iso-ButyZamine~
Refs: l)Beil 12, (445) 2)J.Reilly & W.J. (CH3)2CH.CH2.NH. C6H5, oil, bp 225-7°,
Hickinbottom, JCS 113, 993(1918) d 0.,940 at 18 °(Refs 2 & 3); and te~t
2,3,5-Trinitro.4-(N-butyl. N-nitro)-aminotoluene, - Butylaniline, (CH3)3C.NH.C6H~, oil, bp
C4H9.N(N02).C6H(N02 )3.CH~, mw 343.25, 208-10°(Ref 2). These isomers form trysts
N 20.40%, crysts(from HNO~), mp 87-8°; easily salts, some of which are unstable when heated.
sol in .benz, chlf or boiling methanol or ethanol; Other props & methods of prepn are given in
SI sol in cold methanol. Can be prepared either the Refs
by crystn of the corresponding rritrosamine from Re/s: l)Beil 12, 168,(160) & [95] 2)Beil 12,
HN03 or by nitration of 2-nitro-N-but ylamino- 168 3)Beil 12, [96] 4)Sax(1957), 398 5)
toluene with HN03(d 1.5) as described in Ref 2. CondChemDict(1961), 183
Its expl props were not ‘investigated N-Nitroso-N-butylaniline, Cl OH, ~N20; mw
Refs: l)Beil 12, (445) 2)J.Reilly & W.J. 178.23, N 15.75%. TWO isomers are described
Hickinbottorn, JCS 113, 993(1918) in the literature: [N-iVitroso-N-( n-butyl)]
-aniline, CH3 .( CH2)3.N(NO).CeH5, grn-yel
Butylammonium Tetrazidocuprate, (C4H9.NH3)2- liq, vol in steam; SOI in alc or eth; v S1 sol in
[CU(N3)4] , mw 379.92, N 51.62%. Two isomers hot w(Ref 1); described by Fierz-David et al
are known: n-ButyZ salt, expl at 178-80° and (Ref 3) as a reddish-brn oil, bp 132° at 13mm;
iso-Butyl salt, mp 125°, e’xpl at 203°; both and [N-Nitroso-N(sec- butyl)] -aniline,
compds expl also under impact. These and C2H5.CH(CHa).N(NO) .C6H5, yel aromatic oil,
other complex salts of cupric azide, vol in steam(Ref 2). Other props & methods of
[CU(N3)21 , were prepd & studied by .Straumanis prepn are given in the Refs
& Cirulis(Ref 2) and by others. See also Cupric Refs: l)Beil 12, 580, (294) 2)Beil 12, [31O]
Azide Complexes; VOI 1, p A5 33-R 3)H.E.Fierz-David et al, Helv 29, 1775(1946) &
Re/s.’ 1)Beil-not found 2)M.Straumanis & A. CA 41, 2411(1947)
Cirulis, ZAnorgChem 252, 9-23(1943)& CA 38, Mononitro.N-butylaniline, C4H9.NH.C6H4.N02;
3564(1944) mw 194.23, N 14.42%. Two isomers are described
in the literature: [2-iVitro-N-(n- butyl) ] -aniline,
C-Butyl-aniline and Derivatives trysts, mp 31-2°; and [4- Nitro-N-(n-butyl) ]
C-Butyl-aniline, C-Butyl-arninobenzene or - aniline, trysts, mp 54°. These compds were
Aminobutylbenzene, C4H9.CGH4.NH2, rnw prepd in excellent yi elds by heating 2- or
149.23, N 9.39%. Six isomers are described in 4-nitrofluorobenzene with n-butylamine in w with
Beil 12, 1166, (503,505) & [633,636 & 637] Na2C03, K2C03 or magnesia
Monoitm-C-butyz-@ iline, C~H9.CGH3(N02.NH2, Re/.s: l)Beil-not found 2)R.L.Lantz & P.
mw 194.23, N 14.42%. Five isomers are described Obellianne, BullFr 1956, 311-17 & CA 50,
in Beil 12,1166,1169 & [634,637] 15444(1956)
Dinitro-C-butyl-aniline, C-butyl-aniline, Dinitro.N.butylaniline, C4H9.NH.C6H3(N02 )2;
C4H9.C6H2(N02)2 .NH2, mw 239.23, N 17.57%. mw 239.23, N 17.57%. The following isomers
One isomer, 2, 6-Dinitro-4-(tert-buty l)-aniline, exist: [2, 4-Dinitro-N-(n-butyl) 1 -aniline,
(CH$ )3 C.C6H2(N02)2.NH2, yel trysts, mp CH3 .(CH2)3 .NH.C6H3(N02)2, yel ndls(from
127 , is described in Beil 12, 1169 alc or petr eth), mp 90-30; readily SO1 in chlf,
Trinitro-C-butyl-aniline, C4H9.C6H(N02)3.- benz, ale, eth, acet, AcOH & AC20; sol in petr
NH2, mw 284.23, N 19.71%. Not found in Beil eth & CS2; was prepd by heating 2,4-dinitro-
or CA through 1960 chlorobenzene with n-butylamine & alc at
100 °(Refs 2, 4 & 6); [3, 5-Dinitro-N-(n-buty l)]
N-Butylaniline and Derivatives -aniline, yel plates, mp 99°; was separated by
 B 379

partition chromatography from a mixt of Refs: l)Beil 12,,764 2)Bei1 12, (368) 3)P.
secondary amines, obtd by heating 3,5 van Romburgh, Rec 4, 193( 1885) 4)A.P.No
-dinitroaniline hydrobromide with n-butyl aIcohol Franchimont, Rec 291, 300(1910) 5) R. Weiss &
in a sealed tube at 100 °(Ref 7); [2, 4-Dinitro-N A. Abeles, Monatsh 59, 238(1932) & CA 26,
-(.sec-butyl)] -aniline, CzH~.CH(CH~).NH.- 2414(1932)
C6H3(N02)2, yel trysts, mp 56°; was prepd by Tetranitrobutylaniline, C .IOHI ,N508; mw
heating an alcoholic solrr of l-chloro-2,4 329.23, N 21.27%. Two Isomers are known:
-dinitrobenzene with sec-butylamine at 100° [2,4,6-Trinitro-N-nitro-N-(n-butyl)]aniline;
for several hrs(Ref 5); [2, 4-Dinitro-iV-(iso sym - Trinittopben yLN-(n-buty~nitram ine):
-butyI) ] -aniline, (CH3)2.CH.CH2.NH.C6 H3- (2, 4; 6- T~nitro~henylnitramine) -n-6utane or
(N02)2, yel monocl prisms(from CS2), mp 80°, “Butyltetryl’‘ (called N-Nitro-N-butyl-N
d 1.342 at 20°(Refs 1 & 3); and [2,4-Dinitro-N -2.4.6-trinitroaniline; N-Butyl-2.4.6
-(tert-butyl) ] -ardine, (CH3)3 .C.NH.C6H3(N02)2, -tetranitroanilin or Butyl-pikryl-ni tramin in
yel crysts(from diI aIc), mp 1190; was prepd Ger), CH3.(CH2)3 .N(N02).C6H2(N02 )3, It yel
from l-chloro-2,4-dinitrobenzene and temt Ifts(from AcOH) or lemon yel plates(from ale);
-butyIamine(Ref’ 8). The expl props of dinitro mp 98-100°; readily sol in benz, ethyl acet,
-N-butylamines were not investigated alc or acet; ‘insol in petr eth; was first prepd
Re/s: l)Beil 12, 751 2)Beil 12, [406] 3)P. by Franchimont(Refs 2 & 4) from picrylchloride
van Romburgh, Rec 4, 192(1885) 4)E.J. and the K salt of n-butylnitramine in warm alc
van der Kam, Rec 45, 732(1926) & CA 21, 404 and also by nitrating N-butyl-2,4,6
( 1927) 5)J .J.Blanksma & H. H. Schreinemachers, -trinitroaniline with absol HN03; Davis(Ref 6)
Rec 52, 430(1933) & CA 27, 5065(1933) 6)Davis prepd the compd by condensing l-chloro-2,4
(1943),P 183 7)J.C.Roberts & K.Selby,JCS -dininobenzene with n-butylamine and nitrating
1949, 2787 & CA 44, 3922(1950) 8)0. L.Brady & the product and also by nitrating, in one step,
F. R. Cropper,JCS 1950,516 & CA 45,8971(1951) n-butylaniline(See also Refs 5 & 7)
Trinitro-N-butylaniline, C4Hg.NH.C~H2(N02 )3; Butyltetryl is an expl comparable in
mw 284.23, N 19.71%. The following isomers power &brisance to TNT(97.5% TNT by
are known and described in the literature: Ballistic Mortar Test and the same as TNT by
[2,4,6-Trinitm-N-(n-butyl)] -aniline; (2,4,6 Sand Test); its sensitivity to impact is ca the
- Trirzitropbenylarnino)-n-butane; (2, 4,6 same as that of TetryL It expl at 210° and is SI
- Trinitropbenyl)-n-butylamine or N-(n-Butyl) more sensitive to initiation that Tetryl(O.4g
-2,4, 6-trinitroaniline, CH3(CH2)3.NH.- requires O. 19g MF vs 0.24g MF for 0.4g
C6H2(N02)3, orn-yel nds(from petr eth), mp Tetryl). Butyltettyl was recommended for use
80.5-81°; readily sol in benz or chlfi less sol in boosters, reinforced detonators, detonating
in petr eth; was prepd by condensing picryl fuse & priming caps(Refs 8, 9 & 10)
chloride with n-butylamine in alc(Refs 2 & 4); [2,4,6-Trinitro-N-nitro-N-(iso-butyl)]
2,4,6- [ Trinitro-N-(see-bytyl) ] -aniline or -aniline or iso-Buty Lpicryl-nitramine( called
N-(see-Butyl)-2, 4, 6- Trz”nitroaniline, N-Isobutyl-N.2.4 .6-tetranitroanilin or N-Nitro
C2H5.CH(CH3).NH .C6H2(NOZ)3, yel trysts, -N-isobutyI-2.4 .6-trinitroanilin in Ger),
mp 78-80°; was prepd from D L-sec-butylamine (CH3)2CH.CH2.N(N02 ). C6H2(N02)3, yel ndls
(2 moles) and picryl chloride(l mole) in ale; (from ale), mp 110°; was prepd by nitrating
compd has only S1 basic props; its HC1 salt is either N-isobutyl-2,4-dinitroaniline or 2,4,6
decompd by w(Ref 5) and [2,4, 6- Trinitro-N -trinitroaniline with fuming HN03(Refs 1 & 3).
-(iso-butyl)] -aniline or N-(iso-But$-2, 4,6 It is an expl SI less powerful & brisant than TNT
-Trinitroarzilirze, (CH~ )2 CH.CH2 .NH.C6H3- Re/s: l)Beil 12, 771 2)Beil 12T (371) & [426]
(N02)3, lt yel lfts(from acet or CS2), mp 95°, 3)P. van Romburgh, R~c 4, 193(1885) 4) A.P.N.
d 1.445 at 18°; was prepd by reacting picryl Franchimont,Rec 29,301 (191O) 5) J.ReiUy &
chloride with iso-butylamine in alc soln(Refs W. J. Hickinbottom, JCS 117, 135(1920) & CA
1 & 3). The expl props of these trinitro 14, 1819(1920) 6)T.L.Davis, USP 1607059
-butylanilines were not reported (1926) & CA 21, 3~5(1927) 7)M.S.Fishbein,
Note: CA Formula Index 1920-1946, P 425, VoennayaKhim 1933, No 6, pp 3-8; ChemZtr
lists N-(tert”butyl)-picramide as being described 193411, 1074-5 & CA 29, 7077(1935) 8)Davis
in CA 26, 2414. We could not find the compd (1943), 183 9)Blatt,0SRD 2014(1944) 10)
in CA Perez Ara(1945), 591
 B 380

Butylanisole and Derivatives -benzamide [called by us N-(1,1, l-Trinitro-sec

ButyIanisole or Butyimetbo.vybenzene, -butvl)-benzamide or N-(Trinitro-l-m ethyl
C4H9.C6H4.0.CH3. Several derivs are described -propyl)-benzamide] , Cfi3.CH2.$H.NH.-OC.C6 H5,
in Beil 6, 522, (257) & [485] C(N02)3
Dinitrobutylanisole or Dinitromethoxybenzene,
is described in Conf US Rubber CoQuartProg
C4H9.C6H2(N02)2 .0.CH3, mw 254.24, N 11.02%.
Rpt No 15(1 May to 1 Aug, 1951),P 5
One isomer 5-(tert-Buty~)-2, 4-dinitroanisole,
Re/s: l)Beil-not found 2)E.H.White, JACS
yel ndls, mp 80-1°, is described in the literature.
77, 6020-1(1955) & CA 50, 8527(1956)
It is used for the prepn of trinitro compds
Re/s: l) Beil-not found 2)M.S.Carpenter et al,
Butylbenzene and Derivatives
JOC 16, 607(1951)&CA 46, 1494(1952)
Butylbenzene, Phenyl Butane or Methylphenyl
Tinitrobutylanisole or Trinitrobutylmethoxy-
Propane(called Butylbenzol, Phenylbutan or
benzene, Cl ,Ht3Na07; mw 299.24, N 14.04%.
Methyl-phenyI-propan in Ger), Cl OH I ~; mw
Two isomers are described in the literature:
134.21, N 10.51%. Four isomers exist:
3-( tert-Butyl)-2, 4, 6-trinitroanisole, (CH3 )3 C.-
n-But ylbenzene, CH3(CH2)3 .C6H5, CO1 Iiq,
C6H(N02)3 .0.CH3, pale yel odorless ndls,
fr point -88°, bp 182°, flash p 160°F(TOC),
(from methanol), mp 99.5-100°; was obtd, in
d 0.8601 at 20°(Refs 1 , 4 & 5); sec
addn to a little 5-(tert-butyl)-2,4-dinitroanisole,
-Butylbenzene, CH3.CH2.CH(CH3) .CGH5,
from the mother liq resulting from the nitration
CO1 liq, fr point -75.8°, bp 173°, flash P
of the methyl ether of m-tert-butylphenol( Ref
145 °F(TOC), d 0.8621 at 20 °(Refs 2, 4 & 5);
3); and 4-(tert-Butyl)-2,3, 6-trinitroanisole
iso-Butylbenzene, (CH3)2CH. CH2. C6H ,
(called 2.3.5 -Trinitro-4-methoxy-l-tefi-butyl
COI liq, fr p -120, bp 173°, flash P 126%F(CC),
-benzol in Ger), yel ndls(from ale), mp 74-5°
d 0.867(Ref 3; Ref 4,P 794); tert-Butylbenzene,
(Refs 1 & 2). The expl props of these compds
(CH3) ~C.C~Hs, CO1 Iiq, fr point -58°, bp
were not detd
168°, flash p 140°F(TOC), d 0.8665 at 200
Refs: l)Beil 6, 525 2)A.Baur,Ber 27, 1619
(Refs 3, 4 & 5). Other props & methods of
( 1894) & JCS 66 I, 450(1894) 3)M.S.Carpenter
prepn are given in the Refs
et al,JOC 16, 608(1951) & CA 46, 1494(1952)
Re/s: l)Beil 5, 413, (201) & [317] 2)Beil
5, 414, (202)& [319] 3)Beil 5, 415, (203) &
Butyl Azide. See under n-Butane
[320] 4)Sax(1957), 399 & 794 5)CondChemDict
(1961), 183
Butylbenzomide and Derivatives
Mononitrobutylbenzene, Cl OH, #02; mw 179.21,
Butylbenzamide, C4H9 .NH.0C.C6H5. Several
N 7.82%. A number of isomers of the type
isomers are described in Beil. 9, (97) & [166] ‘.

Butyl-nitrobenzene, C4H9,CGH4.N02, and

Mononitrobutylbenzamide, C4H9.NH.0C.C6H4.-
Nz’trobutyl-benzene, 02 N,C4H8 .C6H5, of
NO . Two isomers are described in Beil
n-, see-, iso-, & tert-butylbenzenes are described
9, ?271]
in the literature. AH of these compds are low
Dirzitrobutylbenzamide, C , ,H13N30~ - not
boiling, oily liquids, some of which are unstable.
found in Beil
Their props & methods of prepn are given in
Trinitrobutylbenzamide, C,, HI ~N407, mw
Beil 5,414,415,417,418, (201,202,203) &
312.24, N 17.95%. Three isomers are dkcussed
[318,319,320,321]
in the literature: N-(n-But yl)-N, 3, 5-trinitro-
Dinitrobutylbenzene, CIOH1 *N204; mw 224.21,
benzarnide, CH3(CH2)3.N(N02 ).0C.C6H3(N02 )2,
N 12.50%. The following isomers are described
no props given; was obtd as the residue from
in the Literature: 2, 4- Dinitro-l -(see-butyl)
reaction of 3,5-dinitrobenzoyl chloride with the -benzene, CzHs.CH(CH9).C6 H3(N02)z, liq,
Na salt of N-nitrobutyl-amine( Ref 2);
bp 143-4° at 2mm & 161-2° at 5mm, d 1.2195 at
N-(sec. butyl)-N,3, 5-trinitrobenzamide,
25°, n~ 1.5534 at 14.3 °(Ref 3); 2, 4,-Dinitro-l
C2~H~.CH(CH3).N( N02).0C.C~H3(N02 )2, prepn -(iso-butyl)-benzene, (CH3)2CH.CHz.CGH3-
& props to be reported by White(Ref 2); and
(N02)2, liq, bp 158-9° at 2mm, d 1,2134 at
N-(iso-butyl)-N, 3, 5-trinitrobenzamide,
25°, n 1.5479 at 25 °(Ref 3); 2,4, -Dinitro-l
(CH3),CH.CH2.N(N02 ). C6H~(N02)2, -(tert-~utyl)-benzene, (CH,),C.CGH3(NOZ)Z,
prepn & props not given(Ref 2). Their expl
yel to CO1 prisms(from dil ale), mp 61-2°, bp
props were not detd
185° at 15mm(Refs 1,6,7,8 & 9); UV spectra
An expl compd, N-(I, 1,1 -Trinitro-2-buty 1)
(Ref 5). Other props and methods of prepn of
 B 381

dinitrobutylbenzenes are given in the Refs F. Noto, Gazz 43 I, 519(1913) & JCS 104 I,
The dinitro derivs of see- & tert 716(1913)
-butylbenzenes were proposed as ingredients of
plastic expls contg PETNor RDX(Ref2) and as Butylcarbinol. See Amyl Alcohols; Vol l,p
ingredients of a plastic dynamite(Ref 3) A394
Re/s: l)Bei15,418, (203)& [321] 2)H.R.
Wright &W. G. Allan, BritP 5806012(1947)&CA Butyl“Cellosolve”, Glycol Monobutyl Ether
41, 7120(1947) ,3) T. E. Zalesskaya, or 2-Butoxyethanol( called Athylengly-
ZhObshchKhim 17, 489(1947) & CA 42, 844 kolmonobuty121ther in Ger), C4H9.0.CHz.-
(1948) 4)H.R.Wright &W.G.AUan, USP CH2.0H; mw 118.17, 0 27.08%; CO1 liq, fr
2439328( 1948) &CA 42,4350(1948) 5)T. point <-40°, bp 135°, flash p 141 °F(CC),
Canback, Farm Revy(Stockholm) 48, 217, 234, d 0.9311 at 20°; MAC 200ppm in air or 965mg
249(1949)I& CA 43,6175(1949) 6)M.S. per ma @ air(Ref 2). Other props & methods of
Carpenter et al, JOC 16, 586(1951) & CA 46, prepn are given in Refs 1, 2 & 4
1495(1952) 7)H.J.B.Biekart etal, Rec 71, Ii is used as a SOIV for NC, resins, oils &
332(1952)& CA46,fl127(1952) 8)N.M.L~fgren other materials. Zenftman & Forlin(Ref 3)
&B. Takman,ActaChemScand6, 1006(1952)& patented fwse compns which cqn be continuously
CA 47, 8027(1953) ~N.M.CuHinane& D.M. extruded provided a thermoplastic binder or
Leyshon, JCS1954,2942&CA 49, 12323(1955) special antihardening agent is included in the
Trinitrobutylbenzene, C10H11N306; mw 269.21, formulation. Such a compn consisted of fuse
N 15.61%. The following isomers are known: powder 79.6(a mixt of Pb304 41, KN03 33 &
2,4-Dinitro-l-(2 -nitro-iso-butyl) -benzene or Si 26%), colloided NC 20(NC 50, dibutyl-
2, 4-Dinitro-l -(2-methyl-2 -nitropropyl)-benzene, phthalate 48 & DPhA 2%) and 0.4% butyl
( CH3 )2.C(N02).CH2 .C6H3(N02)2, trysts, mp “Cellosolve.”, or citric acid, or KHC204 .H20
68-9°; was prepd by reaction or 2 ,4-dinitrobenzyl Re~s: l)Beil 1, [519] 2)Sax(1947), 402
chloride with Na salt of 2-propanenitronate 3)H.Zenftman & J. E. Forlin, USP 2590060
(Ref 3) and eso-Trinitro-(tert-buty l)-benzene, (1952) & CA 48, 6700(1954) 4)CondChemDict
(CH3)9C.C6HZ(N02 )3, yel wh ndls(from ale), ( 1961), 468
mp 1!)8-9°; was prepd by nitrating dinitro-tert
-butyl-benzene( Refs 1 & 2). The expls props of Butyl Centralite. See under Centralizes
these compds were not detd
Re/s: l)BeiI. 5, 418 2)A.Baur, Ber 27, 1610 Butyl-N-chloronitramine. See under Butylamine
(1894) & JCS a I, 445(1894) 3)H.B.Hask &
M. L.Bender, JACS 71, 3485(1949) & CA 45, Butylcresol and Derivatives
131(1951) Buty~cresol, Butylbydroxytoluene or
But ylbydroxyrnetby lbenzene(Butylkresol in
But yl Borate. See under Berates Ger), C4H9 .C6H3(CH3 ).OH. Several isomers
are described in Beil 6,550 & [507]
But yl Butyramide, Trinitro Derivative. An expl Nitrobutylcresol, C,, Ht ~N03. Several isomers
compd called N-(1,1,1 -Trz”nitro-2-butyl) are described in the literature
-butyramicfe, H3C.CH2.CH2.C0.NH.$H.CH2 .CH3, Refs: CA’s 24, 3469, 29, 13392; 31, h58a;
C(N02 )3 43, 3805a, 49, 13145ef & 13175g; 50, 6509a&
is described in Conf US Rubber Co Quart Prog, 8727g
Rept No 15(1 May-1 Aug, 1951),P 4 Dinitrobutylcresol, C ,, H, ~NzU5. Several
isomers are described in the literature
n. Butylbutyrate,4,4,4= Trinitro. See n-Butyl Re/s: CA’s 31, 46587; 45, 9500f and 49,
-4,4,4-trinitrobutyrate 13175e
Trinitrobutylcresol, Cl, HI ~N~07; mw 299.24,
i so. Butylcarbamyl Azide(called N-Isobutyl N 14.04%. Two isomers are described in the
-carbamidsihreazid in Ger), (CH~)z CH.- literature: 5-(tert-Butyl)-3, 4, 6-trinitro-o-cresol;
CHZ.NH.C0.N3; mw 142.16, N 39.41%; liq, 5-(tert-Butyl)-2 -bydmxy-l-methyl-3, 4,6
bp 94° at 22mm; sol in alc or eth; was prepd -trinitrobenzene or 5-(tert-Butyl)-2-~ dmxy-2
from iso-butylisocyanate and HN3 in eth -bydroxy-3, 4, 6-trinitrotoluene( called
Refs: l)Beil 4, (376) 2) E.Oliveri-Mandalk & 2.4.5 -Trinimo-tixy-l-methy l-3-tert-butylbenzol
 B 382

in Ger), 02N.~ = C(CH3)+J .OH and others. These and other ethers of glycol &
(H~C),C.C= C(NO,)- 2 .NO, glycerol can be used as SOIVS for NC and other
yel ndls(from ale), mp 85-6°; was prepd by the cellulose esters, in the dyeing & explosives
action of Hh703 on butyl-o-cresol in glacial industry, and as cooling liquids for internal
AcOH at low temp(Refs 1 & 2); and ~-(tert combustion engines
-Butyl)-2, 4, 6-trinitm-m-cresol; 5-(tert-13ut yl) Refs: l)Beil 1, {2084, 2188} 2) K. R. Edlund,
-3-b ydroxy- I -metb yl-2, 4, 6-ttinitrobenzetze or USP 1968032(1934)&CA 28, 5832(1934) 3)T.
5-(tert-Butyl)-3 -bydroxy-2, 4, 6-trin itrotoluene, Evans & K. R.Edlund,USP 1968033(1934) & CA
02N.$ = C(CH3)- $.N02 ; 28, 5832(1934)
(H3C)3C.C = C(NO# C.OH
trysts, mp 1040; was prepd by nitrating Butylene Oxides; Tetrahydrofuran or
5-(tert-butyl)-3 -hydroxytoluene in benz with Tetramethylene Oxide, C4HeO; mw 72.10,
HN03 at low” temp(Ref 3). Their expl prop’s 0 22,19%. Several isomers are known, A Iiq
were not investigated mixt of isomeric butylene oxides has the props:
Refs: l)Beil 6, 550 2)A.Baur, Ber 27, 1614 bp 62-5°, flash p 5°F, pour p -150°, d 0.826
at 25°, vap d 2.49; highfy toxic liq; dangerous
(1894) & JCS 66 I, 4@(1894) 3)B.M.Dubinin &
N. E. Kozhevnikova,ZhObshihKhim 21, 662(1951) when exposed to heat or flame; expl range 1.5
& CA 45, 9500(1951) to 18.3%(Ref 2). Other props & methods of
prepn are given in the Refs. The 1,4-isomer
(tetrahydrofuran or tetramethylene oxide) is
described in detail in the Refs. Butylene
oxides are used as SOIVS & as org intermediates
Butylene. Same as Butene Z?e/s.’ l)Beil 17, 10, (5) & [15] 2)Sax(1957),
405 & 1166 3)CondChemDict( 1961), 186 & 1122
Butylene Glycol. Same as Butanediol
Butylene Ozonides. Harries et al(Refs 1 & 2)
iso-Butylene Glycol. Same as iso-Butanediol prepd the normal monomeric ButyIene Ozonide,
(CH3.CH6-)203; mw 104.1O, 0 46.11%; liq,
Butylene Glycol Ethers. Several butylene glycol bp 15-16 at 20mm, d 1.0217 at 22°, n~
ethers are known and described in the literature. 1.3855 at 22°; decomp and turns brown with
Edlund(Refs 1 & 2) prepd iso-butylene glycol NaOH; expl violently when heated in a tube to
-2-monomethyl ether [ called 2-Methoxy-2 ca 125°; was obtd in addn to the dimeric
-methyl-propanol-(1) in Ger] , (H3C)2C(OCH3 ).- ozonide by the reaction of butylene and ozone
CH2.0H, mw 104.15, 0 30.73%, liq, bp 142° at in Iiq methyl chloride; normal dimeric Butylene
765mm, d 0.9333 at 20°, n~ 1.4190 at 20°; and Ozonide, [(CH,.CH,)2031 z; mw 208.21,
iso-Butylene Glycol-2-monoetbyl ether, [called 0 46.11%; viscous Iiq, almost odorless, bp
2-~thoxy-2-methyl-propanol-(1 ) in Ger] , expl when heated to ca 125°, d 1.17 at 200;,
(H3C)2C(OC2H5).CH2 .0H, mw 118.17, 0 27.08%, sol in most org solvs; v S1 sol in w. Using
liq. bp 148, d 0.9073 at 20°, n~ 1.4193 at 20°. cccrude’’(unwash@d) 03, Harries et al(Refs 1 & 2)
These ethers were proposed as SOIVS for NC & also obtd monomeric Butylene Oxozonide,
other cellulose esters C4Ha04; mw 120.10, 0 53.29%, Iiq, bp 20-2° at
Evans & Edlund(Ref 1 &3) reacted an 20mm, d 1.0336 at 20°, n~ 1.38404 at 20°; and
aliphatic polyhydri c alc with t err-but yl ene in dimeric Butylene Oxozonide, (C4He04)2; mw
the presence of a condensing agent(such as 240.21, 0 53.29%; oil like glycerol and smelling
H2S04) and obtd the following ethers: like Paraldehyde, fr p -80° solidifying ro a glassy
mono -tert-Buty~ether of Ethylene Glyco~ mass, bp dec & expI violently when heated to
(called ~thylengylkol-mono-tert-butyliither in ca 125°, d 1.1604 at 19°, n~ 1.43167 at 19°;
Ger), (H3C)3 .C.0.CH2.CH2C)H, mw 118.17, readily sol in org SOIVS, except petr eth or w.
0 27.08% liq, bp 152.5° d 0.8970 at 20°, All of these ozonides are decompd by w into
n~ 1.41322 ar 25°; tert-Butyl-metbyletber of acetaldehyde, AcOH, H202 & O
Ethylene Glycol(called ~thylenglykol The ozonization of butylenes, aldehydes
-methyl~ther-tert-butyl~ ther in Ger), & acetone both in the gaseous phase and in
(H3C)3.C.0.CH2. CH,.0.CH3, mw 132.20, soln at low temp has been described by Briner
0 24.21%, liq, bp 131-2°, d 0.8399 at 20°; & Meier(Ref 3). They obtd the same expls
 B383

ozonides as Harries(Ref 2); and by hydrolysis & amine are also known & described in the
study of the products formed, Briner & Meier Iiteratuqe
were able to distinguish one ozonide from Refs: l)Beil 4, 283 2)Sax( 1957), 405 3)Cond-
another ChemDict(1961), 188
Rieche & Meister(Ref 4) found that Butylethanolamine Dinitrate, C4H9 ,NI-I.CH2.-
cautious heating of butylene ozonide in vacuo CH2(ON02).HN03; mw 225.20, N 18.66%; compd
caused it to undergo cleavage and there formed, prepd by nitrating n-butyl-ethanolsmine with
at about 80°, a wh tryst mass which was mixed acid at 0-10° and pptg the product by
extremely expl. This product was identified as pouring into ice & w; was proposed for use as
pure dirneric etbylidene peroxide(Ref 6). In an expl or in expl mixts
the course of a study of ozonides and their Re/s.’ l) Beil-not found 2)Dynamit-AG,BritP
decompn Rieche et al(Refs 5 & 6) prepd 358157(1930) & CA 26, 6141(1932)
2, 3- Butylene Ozonide, CH3 .CH.O.O.CH.CHs, 1-(N-Butylnitramino)-2-nitroxy-ethane or
L~J [l-(N-Butylnitramino)-ethan-2-ol] Nitrate,
bp 35° at 100mm, d 1.027 at 19°; an exP1 compd C4H9.N(NOz).CH2 .CH2.0N02; mw 207.19,
but not sensitive to shock at RT; the distn N 20.28%; pale yel oil fr p -9-9°, no 1.4750
residue was a polymer more stable than the at 20°; was prepd from 2-ethanol-but yl amine,
dimer nitric acid, acetic anhydride & a chloride
Garvin & Schubefi(Ref 7) prepd catalyst such as ZnC12. It was propoi$ed as a
iso-Butylene Ozonide, a CO1 Iiq, expldg violently plasticizer for use in double-base proplnts.
when heated; vap press 25mm at 18.4°) n~ Re/s: l) Beil-not found 2)A.T.BIomquist &
1.388 at 18.0°. They detd its IR spectra as a F.T.Fiedorek,USP 2485855(1949), pp 6, 14 &
means of identification CA 44, 3516-17(1950)
R e/s: l)Beil 1, (85) 2) C. Harries et al, Ann
390,241,245(1912) & CA 6, 2754(1912) 3)E. Butylethylcarbamate. Same as Butylurethane
Briner & R.Meier,Helv 12, 529-53(1929) & CA
23, 5155(1929) 4)A.Rieche & R.Meister, Ber Butylethyltoluene and
72, 1935(1939) & CA 34, 712(1940) 5) A9Rieche Derivatives
et al, Ann 553, 187(1942) & CA 37, 5365, 3-(tert-Butyl)-5-ethyltoluene, H3C(C2Hs).C6H~.-
(1943) 6)Tobolsky & Mevobian(1954)t 50~ 180 C(CH3)3, liq, bp 71° at 2mm, is described in
7)D.Garvin & C.Schubert, JPhChem 60, 807-8 Ref 2
(1956) 3-(tert-Butyl)-5-ethyltoluene, Trinitro Derivative,
H3C(C2H~).CG(N02 )3. C(CH~) ; mw 311.29,
Butyl Ester of Peroxyacetic Acid. Same as N 13.5o%; pale yel stout ndls ?from MeOH),
Butyl Peroxyacetate having a musk odor, mp 75-76.5°; was prepd
by nitrating 3-(tert-butyl)-5 -ethyltoluene. No
Butyl Ester of Peroxybenzoic Acid. Same as expl props of this compd were detd
Butyl Peroxybenzoate Refs: l) Beil-not found 2)M.S.Carpenter & W.M.
Easter,JOC 19, 88,94(1954) & CA 49, 3043(1955)

Butylfuroamide, Trinitro Derivative. An expl

compd called N-(I, 1,1 -Ttinitro-2-buty l)-/uroamide,
Butylethanolamine and
Derivatives CH3.CH$-NH- ?~ ; mw 302.20, N 18.54%;
Butyietbanolamine or Butyiaminoetbanol [ called C(NOZ)3
~-Butyl-amino-2ithylalkohol or ButyI-(@-oxY described in Corif US Rubber Co Quart Prog
-~hyl)-amin in Ger] , CH3 .( CHZ)3 .NH.CH2.- Report No 15(1 May to 1 Aug 1954), pp 5 & 6
CH2.0H; mw 117.19, N 11.95%; CO1 Iiq, bp
199-200° at 756mm, flash p 170°F(OC), Butylguanidine and
d 0.891 at 20°, n~ 1,4437 at 20°; readily sol in Derivatives
ale, eth or w; its toxicity details are unknown; Butylguanidine, C4H9.NH.C(:NH).NHZ; mw
was prepd from butylamine & ethylene oxide 115.18, N 36.49%; may be considered the
(Refs 1 & 2). It forms salts & titrated derivs, parent compd of its various salts & nitrated
some of which are expl. Isomers of butylethanol- derivs; was first prepd by Paden & MacLean(Ref
 I

B 384

3)by the reaction of butylamine and its acid l-n-Butyl-1,3-dinitrogumidine by Meen &
salt with NHZ.CN in aq soln at 80-170°; and Wright), C4H9.N(N02).C(:NH)*NH-N0Z3 ‘w
later prepdby Roche et al(Ref4)by theoxidn 205.18, N 34.14%; crysts(from chlf + CC14),
of arginine in aq alk soln. Davis & Elderfield mp 71-2°; compd is 0.4% sol in w at 25°; very
(Ref 2) had earlier prepd salts of butylguanidine, sol in most org SOIVS; was prepd. by treating
such as its Nitrate, mp 69° and picr~e. mp l-(n-butyl)-2-nitroguanidine, [C4H9.NH.C(:N.N02 ).-
154.5°. A number of other investigators have NH2] , with HN03 & AC20 for lhr at 20-2°.
since prepd these & other salts of butylgaunidine This compd was rapidly cleaved by dil KOH to
Re/s: l) Beil-not found 2)T.L.Davis & R.C. yield K nitrocyanamide & n-butylnitramine,
Elderfield, J ACS 54, 1499(1932) & CA 26,2708 isolated as the monohydrate of the Ba salt.
(1932) 3) J. H. Paden & A. F.MacLean,USp The expl props of the dinitro deriv were not
242534X1947) & CA 41, 7414(1947) 4)J.Roche detd
et al, BullSocChimBiol 37,55(1955) & CA 50, Refs: l)Beil-not found 2)R.H.Meen & G.F.
4022(1956) Wright, JACS 74, 2077-79(1952) & CA 48,26oo
Mononitrabutylguanidine or Butylmononitro- (1954)
guanidine, C5H12N402; mw 160.18, N 34.98%.
The following isomers are described in the Butyl Hydride. Same as n-Butane
literature: N ‘- Nitro-N-butylguanidine,
CH3(CHz)~NH.C(: NH). NH.N02, ndls(from W) or Butylhydrindene and Derivatives
prisms(from ale), mp 84-5 °(Refs 1,3,4,5 & 8); 5-(tert-Butyl)-hydrindene, C, ~H, ~, Iiq,bp
IR spectra(Ref 6); N’-Nitro-N-(iso-butyl)-guanidine, 237-40°, is described in Refs 1 & 2
(CH3)2.CH.CH,.NH.C( :NH).NHoN02, CO1 pltks 6, 7- Dinitro-5-(tert-bu tyl)-bydtindene,
(from aq ale), mp 121-22°(Refs 2,3,4,5 & 8); and Cl ~H1 ~(N02)2, trysts, mp 121-4°(Refs 1 & 2)
N’ -Nitro-N(tert-bu tyl)-guanidine [ called l-(t 4,6,7-Trinitro-5-(tert-butyl)-hydrindene or
-butyl)-3-nitroguanidine by Fishbein & 4,6,7-Trinitro-5-(tert-butyl)-indan,
Gallaghan] ,( H3C)3.CNH.C(:NH) .NH.N02, COI 02N.$ = C(N02)-$-CH
crysts(from MeOH), rnp 199-20 1°; was prepd by ‘CH2;
(H3C)3C.C = C(N02)-C-CH<
heating tert-butylamine, 2-methyl-l(or 3)-nitro-2
mw 309.27, N 13.59Yo; crysts(from ale), having
-thiopseudourea & abs alc on a w bath at 45°
an odor of musk, mp 1400; was prepd by nitrating
for 6 min(Ref 7). Methods of prepg the other
the dinitro deriv w;.th mixed acid at 50-5°. No
isomers ale given in the Refs
expl props were detd
Refs: l)Beil 4, [635] 2)Beil 4, [640] 3)T.L.
Refs: l)Beil 5,506, [400] 2) Fabrique de Th~n
Davis & S.B.Lute, JACS 49,2303-5(1927) & CA
et Mulhouse, GerP 80158; Frdl 4, 1295(1894-7)
21 ,3348(1927) 4) A. F. McKay & G. F. Wright,
JACS 6 9,3029(1947)& CA 42,1567(1948) 5)A.Fc
Butylhydroperoxide or Butylhydroxyperoxide
McKay,USP 2559085(1951) &“CA 46,3562(1952)
(called Butyl-hydroperoxyd in Ger), C4Ht ~02;
6)E.Lieber et al, AnalChem 23,1594-1604(1951)
mw 90.12, N 35.51%. Four isomers are
& CA 46, 3857(1952) 7)L.Fishbein & J.A.
described in the literature: n-Butylbydroperoxide,
Gallaghan,JACS 76,1879(1954) & CA 49,6838
CH3 .( CH2)2 .CH2.0.0H, liq, azeotrope bp
(1955) 8)A.F.McKay, CanP 519448(1955) & CA
28-9° at 100mm(Ref 7),pure compd bp 40-2° at
50, 12107(1956)
8mm(Ref 9); d 0.9078 at 20°, n~ 1.4032 at
N-Nitroso-N-(n=butyl)-N’-nitroguanidine [called 200; was previously reported as a pro
l-Butyl-3-nitro-l-nitrosoguanidine in CA 5th -knock additive in a spark ignition engine(Ref
Decennial Formula Index(1947-1956),p 132F] ,
6), but its props & method of synthesis were
CH3.(CH2)3.N(NO) .C(:NH).NH.N02; mw 193.16,
detd by Lindstrom(Ref 7): a relatively stable
N 21.76%; ctysts(from MeOH), mp 121 °(dec);
compd not detonated by impact or by heating in a
was prepd by nitro sation of but ylnitroguanidine
free flame; its thermal decompn was studied by
dissolved in aq HN03 soln(Ref 2)A compd,
Thomas(Ref 11) and by Mosher & Wurster(Ref
patented by McKay(Ref 3), was called l-butyl-l
12); Williams & Mosher(Ref 9) reported a new
-nitroso-2-nitroguanidine, mp 113°
& practicai synthesis by the reaction of n-butyl
Re/s: l)Beil-not found 2)J .F.McKay,JACS 71,
methane sulfonate with 30% H202 and Walling &
1969(1949) & CA 43, 9035(1949) 3)J ..F.McKay,
Buckler(Ref 13) by addn of Grignard reagents to
USP 2555498(1951) & CA 46,1034(1952)
oxygen-saturated SOIVS; IR spectra were detd by
N-Nitro-N-(n-butyl)-N’.nitroguanidine(called
 B 385

Williams & Mosher(Ref 10); sec-Butyl 77,6032(1955) & CA 50,8505(1956) 14)D.A.

-hydroperoxide, C2H~.CH(CH3).0.0H, liq, Skoog & A.B ,H.Lauwzecha, AnalChem 28,
azeotrope bp 36° at 100mm(Ref 7)* pure compd 825(1956) & CA 50,10561(1956) 15)S@1957),
41-2° at llmm(Ref 9), d 0.868 at 20°, n~ 406 16)CondChemDict( 1961), 186
1.4269 at 25°; was previously reported as a tert-Butylhydroperoxide.p.nitrobenzoate,
pro-knock additive in a spark ign engine(Ref 6), q
but its props & method of prepn were detd by (H3C)3.C.0.0.C. C6H4.N02, mw 239.22, N 5.86%,
Lindstrom(Ref 7); a relatively stable compd not O 33,44%; thin yel lfts(from MeOH), mp 78°; was
detonated by impact or by heating in a free prepd by reacting the peroxide with the calcd amt
flam~ its thermal decompn was studied by Thomas of p-nitroben zo ylchloride in abs pyridine. A
(Ref 11); Williams & Mosher(Ref 9) reported a number of other hydroperoxide-nitrobenzoates are
synthesis by the reaction of sec-butyl methane expl compds
sulfonat e with alk H202 in MeOH; IR spectra were Re/s: l)Beil-not found 2)R.Criegee & H.
detd by Williams & Mosher(Ref 10); polarographic Dietrich,Ann 560,138(1948) & CA 43,6189(1949)
study by Skoog & Lauwzecha(Ref 14); iso tert-Butylhydroperoxide, Oxalic Acid Ester(no
-Butylhydru#I eroxide, (CHa )2 CH.CH2 .O.OH, liq; formula given in Ref 1). An expl compd which
was reported as a pro-knock additive in a detonated on removal from a freezing mixt
spark ignition engine(Ref 6)’ but its props & Refs: I)W.E .Vaughan, private communication
method of prepn were not given; and tert cited in Tobolsky & Mesrobian(1954), 178 2)CA
-Buty~bydro~eroxide, (CHa)a C. O. OH, liq, fr p Decennial Index 1947-1956-not found
3.8-4.5°, bp 33-34° at 17mm, flash p 55°F(CC),
d 0.8930 at 20°, no 1.4013 at 200; can be prepd Butylhydroxybenzene. Same as Butylphenol
from anhyd tert-butylaIcohol & H20Z by subjecting
it to fractional distn under reduced pressure in Butylhydroxymethylbenzene. Same as Butylcresol
the presence of dehydrating agents or by other
methods(Ref 1,2,3,5 & 8); it is stable at RT but tert-Butylhydroxymethylperoxide, (CH3 )3 .C.O.O.-
expl violently when heated in an open flame; CH20H; mw 192.21, 0 24.97%; liq, bp 52-53°
explosions can also result if distilled under at 8-9mm, d 0.96 at 200, n~ 1.4128 at 200; was
normal press. Due to its properry of being a prepd by gradually adding tert-butylhydroperoxide
good polymerization catalyst, tert-butylhydro- to 36-8% formalin soln at RT & vacuum distilling
peroxide can be used for curing some polyester the product and also by mixing equimolar amts
tesins(g CPsraplex”) which may be used as fuek of 30Z aq solns of CH20 & (CH~)~C.O.OH,
& binding agents in expl or proplnt compns. It followed by distn(Refs 2 & 3). The product is
has been used in some Aerojet solid proplnts useful as - catalysts for polymerization of
(See RL-206 Propellant under Bentonite and Ref u.nsatd compds
4). The combustion product, manufd by Lucidol Re/s: l)Bei&not found 2)F.H.Dickey,USP
Div of Wailace & Tiernan, Inc, Buffalo, NY is 2400041(1946) & CA 40, 5068(1946) 3)F.H,
a mixt contg tert-butyIhydroperoxide(60% rein), Dickey et al, JACS 71 ,1433(1949) 4)Tobolsky &
di-(terr-butyI)-peroxide & tert-butylalcohoI Mesrobian(1954), 173
Refs: l)BeiI 1, { 1579} 2)N.A.MiIas & S.A.
Harries, JACS 60,2434(1938) 3)N.A.Milas & 2-Butyl-2-(hydroxymethyl)=l,3-propanediol.
D. M.Surgenor, JACS 68,205(1946) q) Aerojet An expl compd listed in Conf ADL Rpt on
EngrgCorpRpt No 192(1946), 16-7 5)R.Criegee & “study of Pure Explosive Compounds”, Part
H. Dietrich,Ann 560,135(1948) 6)D.Downs et al, IV(1952),P 586
TrRoySoc 243A,299(1951) & CA 46,244(1952)
7)E.G.Lindstrom, JACS 75,51 24(1953) & CA Butylhydroxytoluene. Same as Butylcresol
49,7846(1955) 8)Tobolsky & Mesrobian(1954), 3,
158 & 177 9)H.R.WiHiams & H.S.Mosher, JACS iso.Butylmalonic Acid
76,2984(1954) & CA 49,8783(1955) 10)H.R. and Derivatives
Williams & H.S.Mosher, AnalChem 27,517(1955) iso-Buty/mrdonic Acid [ called Isobutylmdonsawe
& CA 49,10061(1955) ll)J.R.Thomas, JACS or 3-Methyl-butan-dic~bns5ue< 1. 1) in Ger] ,
77, 246(1955) & CA 49,508 9(1955) 12)H.S. (CH3)2CH.CH2.CH(COOH) ; mw 160.17, 0.39.96%;
Mosher,& C.l?.Wurster,JACS 77, 5451(1955) & CA crysts(from benz ), mp 108 a , dec on continued
50,6305(1956) 13)C.Walling & S.A.Buckler,JACS heating at 11 5°; sol in w, alc or eth; other props
 B 386

& methods of prepn are given in Beil 2,683, 3)DictGuidedMissile s(1959), 106 4) CondChemDict
(284) & { 1756} (1961),187,622
iso-B ut ylmalonic Acid Monoh ydram”de,
(CH3)2CH.CH2.$H(COOH); mw 174.20, N 16.08%; Butylmethoxybenzene. Same as Butylanisole
C0.NH.NH2
pltlts(from dil eth), mp 154-55°(dec); sol in alc Butylmethoxymethylbenzene. Same as
or w; was prepd by heating the K salt of iso Butylmethylanisole
-butylmalonic acid monoethyl ester with hydrazine
hydrate(Refs 1 & 2) Butylmethaxytoluene. Same as Butylmethylanisole
Refs: l)Beil 2,{ 1757} 2) T. Curtius & M.
Schenck, JPraktChem 125, 255,256(1930) & Butylmethylaniline. Same as Butylaminotoluene
CA 24,3216(1930)
iso-Butylmalonic Acid Monoazide, Butylmethylanisole and Derivatives
(CH3)2CH.CH2.$H(COOH); mw 185.18, N 22.69%; Butyimetbylanisole, ButyImetboxymetbylbenzene,
C0.N3 or Butyl~etboxytoluene( called Methylkither des
yel oil having a pungent odor, expl mildly when Methyl-butyl-phenol, Methoxy-methyl-butyl
heated, producing a fl~e; was prepd by -benzol, or Butyl-kresol-methyli!ther in Ger),
treating an eth soln of the monohydrazide & C4H9.C6H3(CH3).0CH3. Two isomers of
NaN02 in dil NaOH with coned HC1 and cooling tert-butylmethyl anisole are described in the
(Refs 1 & 2) literature
Refs: l)Beil 2, { 1757} 2)T.Curtius & M. Refs: l)Beil 6,55o & [507] 2)A.Baur,Ber 27,
Schenck, JPraktChem 125,257( 1930) & CA 24, 1614-19(1894) & JCS 66 1,450(1894)
3216(1930) Dinitrometby~anisoZe, Cl *HI ~N205, ,mw 268.26,
iso.Butylmalonic Acid Amide Azide, N 10.44~. Two isomers are described in the
(CH3)2CH.CH2.$H(CONH2); mw 184.20, N 30.42%; literature
C0.N3 Re/s.’ l)Beil 6,550 (mentioned only) 2)A.Baur,
ndls, mp 87°(dec), expl mildly when heated on a Ber 27, 1614-19(1894) & JCS 66 I, 450(1894)
spatula; sol in alc or benz; S1 sol in eth, chlf or 3)H.Barbier,Helv 11,158 & 160(1928)
CC14; almost insol in w; was obtd when the Trinitrobutylmethylanisole, Cl ZHI ~N307, mw
monohydrazide was treated with HN02 in the 313.26, N 13.42%. Two isomers are described
absence of ether(Refs 1 & 2) in the literature: 2,4, 6- Trinitro-5-(tert-butyl).3
Re/s: l)Beil 2, { 1757-8} 2)T.Curtius & M. -methyl-anizole or 2,4, 6- Trinitro-3-me tboxy-5
Schenck, JPrakChem 125,216,264& CA 24, -(tert-butyl)-tokene, C4H .C (NO )3(CH3).0.,
3216(1930) CH3, It yel trysts, mp 88 8 . ~ari l$e prepd either by
iso-Butylmalonic Acid Nitril Azide, nitration of 5-(tert-butyl)-3-methy l-anisole with
(CH3)2CH.CH2.$H(C!N); mw 166.18, N 33.72%; HN03 in AC20 and then with mixed acid or by
C0.N3 methylation of 5-(tert-butyl)- 3-hydroxy-2 ,4,6
yel oil having a pungent odor, expl when heated -trinitrotoluene with MezS04(Refs 1, 2 & 3); and
in a flame; sol in eth or w; was prepd by treating 3,5, 6. Trinitro-4-(tert -butyl)-2-methy l-anisole or
i so-butycyanoacetic acid hydrazide with NsN02 3,4, 6-Trinitro-5-(tert-butyl)-2-metboxy-toluene,
& an excess of HCl(Refs 1 & 2) yel ndls, having an odor of musk, mp 69-70°; was
Re/s: l)Beil 2,{ 1758} 2) A. Darapsky et al, prepd from the Ag salt of butyltrinitro-ortho
JPrakChem 146,260(1936)&CA 31 ,368(1937) -cresol as described in Ref 2, or by nitrating
butyl-ortho-methoxytoluene(Ref 2). The expl
ButyI Mercaptan, C4H9.SH; mw 90.18. Flammable props of these trinitro-derivs were not detd
1iq having a“skunk-like’’odor. Four isomers Refs: l)Beil 6, [507-8] 2)A.Baur, Ber 27,
exist and they are described in the literature 1614-15 & 1618(1894)& JCS 66 I, 450(1894)
(Refs 1, 2 & 4). Ref 3 lists a butyl mercaptan 3)B.M.Dubinin & N.E.Kozhevnikova, ZhObshch-
with bp 206-10°F(97-990C), sp gr 0.835> fl P Khim 21 .662 -8(1951)& CA 45,9500(1951)
- 162°F(-1080C) which has been considered for
use as a rocket fuel. This material is probably Butylmethylbenzene. Same as Butyltoluene
a coml mixt of various isomers of butyl mercaptan
Refs: l)BeiI 1,370,373,378,383, (187,189,191) & Butylmethylhydroxybenzene. Same as Butylcresol
[398,403,404,405,412,416] 2)Sax(1957),407
 B 387

Butylnitramine. See under Butylamine Corp, Lucidol Division plant at Tonawanda, NY;
and in which 11 persons were kiHed and a number
Butyl Nitrate. See under Butanol of others injured is repotted by Marrin(Ref 10).
Dr Martin proposed a theory-to explain the expln
Butyl Nitrite. See under Butanol and conducted experiments which proved that
rapid heating of butyl peroxyacetate to a critical
Butyl oxalate, H9C4.00.C.C00.C4 H9; mw temp will cause the compd to detonate violently.
202.24, 0 31.64%; Iiq, bp 243°, fl P 265 °F(OC)* According to Martin, a report from the Bureau of
d 0.989-0.993, vap d 7.0; toxicity details are Explosives, Dept of Commerce, indicated in their
unknown(Ref 3); was tried in France as a possible application of heat tests that butyl peroxyacetate
substitute for Centrality in solventless smokeless failed to explode. This was explained on the
proplnts(poudres SD). Proplnts prepd from NC, NG, basis of too low a rate of applying heat. The
4% butyl oxalate & 2% EtCentr were more brittle Bureau did detonate a mixt of the coml liq and a
and less stable than corresponding proplnts contg combustible org compd, such as cotton or
EtCentr alone(Ref 2) woodflour, by initiation with a blasting cap. In
Re/s: l) Beil-not found 2~R.Dalbert & H. inpact tests of the same combustible saturated
Ficheroulle, MP 30,284 & 288(1948) 3)Sax with the liq, no explns occurred under drops of
(1957),410 10in. What actually caused the first mild expln,
the subsequent fire, and detonation of carboys of
Butyl Peroxide. See Dibutyl Peroxide butyl peroxyacetate have not been discovered
Re/s:. l)Beil-not found 2) Lucidol Div, NovadeI
Butyl Peroxyacetate or Butyl Ester of -Agene Corp,Buffalo,NY, Organic Peroxides Data
Peroxyacetic Acid, C6H1 ~03; mw 132.16, 0 36.32% . Sheet No 34(1950) 3)N.A.Milas,USP 2567615
One isomer is described in the literature: ( 1951) & CA 46,3069(1952) 4)E.L.Warrick,USP
tert-lhdyl Peroxyacetate(the coml product of 2572227(1951) & CA 46,772(1952) 5) W.H.T.
Lucidol Div of Novadel-Agene Corp, Buffalo, NY, Davison,JCS 1951, 2456 & CA 46,8965(1952)
is called t-Butyl Peracetate); (CH3)3C.00.0C.- 6)D.Harman,USP 2608570(1952) & CA 48,3387
CHa, clear Iiq, bp 30° at 50mm, d 0.883 at (1954) 7)N.V.de Bataafsche Petroleum
22.5°; n~ 1.403 at 5°, fl p (COC) above 100° Maatschappij, BritP 66371(1952) & CA 47,
(coml product); expl violently when heated 5428(1953) 8)Tobolsky & Mesrobian(1954), 182
rapidly; the presence of benz prevents its expl 9)Sax(1957)-not found 10)J.J.Martin, IEC 52,
decompn(Ref 10); IR spectra was detd by No 4, 65 A(1960)
Davison(Ref 5)
The prepn of butyl peroxyacetate was
patented by Milas(Ref 3) and by Warrick(Ref 4)
who obtd the compd by cooling to 0° a soln of
t ert-butyl hydroperoxide & di-(tett-butyl) peroxide
in pyridine, adding AcC1 at 20-30°, washing with tert-Butyl Peroxybenzoate or Butyl Ester of
aq Naz C03 & W, removing the pyridine, ad distg Peroxybenzoic Acid. (CH3)3C.00.0C.CGH~;
the product at reduced press. Harman(Ref 6) and mw 194.22, 0 24.71%; liq, fr p 8°, bp 113°(dec),
Bataafsche Petroleum(Ref 7) both patented its flash p 66°F(CC), d 1.035 at 25°, vap press
method of prepn by passing gaseous ketene into 0.33mm at 50°, vap d 6.69; very sol in alcohols,
tert-butyric acid, contg a trace of H2S04, over a esters$ ethers or ketones(Refs 6 & 8). Cri egee
period of 1 hr at 0-30° , and isolating the product (Ref 4) reported that when a lab worker attempted
by extraction with pentane to purify tert-butyl peroxybenzoate by vac accdg to
Butyl .peroxyacetate is used as a the method of Milas & Surgenor(Ref 2), a violent
polymerization initiator and catalyst. The coml expln occurred because the distn temp reached 115°
product is described in Ref 2 The props of the coml product which
The expln of butyl peroxyacetate which contains a min of 95% tert-butyl peroxybenzoate
occurred on 23 Sept 1953 in the NOvadel-Agene are given in Ref 3
 I

B 388

Re/s: l)Beil-not found 2)N.A.Milas & D.M. Butyl Rubber. A synthetic rubber produced by
Surgenor,JACS 68, 642(1946) 3) Lucidol Div, copolymerization of isobutene(98%) with a small
Novadel-Agen e Corp, Buffalo, NY, Organic proportion(ca 2%) of isoprene or butadiene.
Peroxides Data Sheet No 27(1949) 4)R.Criegee, Polymerization is conducted at -5o to 100° in a
AngChem 65, 398-9(1943) & CA 47, 11737(1953) liquid hydrocarbon, with A1C13 as catalyst. Lts
5)Tobolsky & MesTobian(l?54), 182 6)Sax(1957), outstanding property compared with other rubbers
410 8)CondChemDict( 1961),188 is impermeability to gases. ,The uncured rubber is
tacky, but it may be compounded like natural
rubber and vulcanized Butyl rubber has good
resistance to chemical attack and to aging even at
high temps. It has superior vibration insulation
characteristics and abrasion resistance, but
Butylphenol and Derivatives relatively low tensile strength and poor flame
Butylphenol or Butylhydroxybenzerze, C , ~H1 ~O. resistance
Several isomers are described in Beil 6,522,524, Important uses of butyl rubber, other than
(259) & [485,487& 489] as inner tubes or similar gas retaining applications,
Nitrobutylpberzol, C, ~Hl ~N03. Two isomers are are as insulators, latex coatings and as binder
described in Beil 6,525 & [488] fuels in solid rocket proplnts
Dinitrobutylphenol, Cl OH, *N205”. One isomer Re/: CondChemDict(1961 ),189
2, 6-Dinitro-4-(tert-buty l)-pbenoI, trysts, mp
97-80, is described in Beil 6, 525 & [489] Butyl Tetryl. See [ 2,4,& Trinitro-N-nitro-N
Butylphenol or Butylhydroxybenzene, Trinitro -(rrbutyl)] -aniline; sym-Trinitrophenyl-N-(n
Derivative. CIOH1 ,N307; mw 285.21, N 14.73%. -butylnitramine~ or (2 ,4,5- Trinitrophenylnitr~ ine)
Only one isomer is described in the liter~ture: -n-butane under Tetranitro derivs of n-Butylaniline
3-(tert-Butyz)-2, 4, 6-trinitropbenol, (CH3)3C.-
CGH(OH)(N02 )3 pale y,el ndls(from ale), mp 172°; Butyltoluene and Derivatives
was obtd by nitrating methyl ether of m-tert Butyltoluene or Butylmetbylbenzene( called
-butylphenol with mixed acid at 10-25°. Its Butyl-toluol of methyl-butyl-benzol in Ger),
expl props were not detd C4HQ.C6H4.CH3; mw 148.24. ,Eight isomers are
R e/s: l) Beil.not found 2)M.S.Carpenter et al, listed in Beil(Ref 1). Sax(Ref 2) lists the p-tert
JOC 16,608(1951)& CA 46, 1493-4(1952) -butyl isomer
Re/s: l)Beil 5,437,439,(209)& [ 333,334]
Butylphthalate. See Dibutylphthalate 2)SaX(1957),413
Mononitrobutyltoluene,. C4H9.C6H9.N02.CH3; mw
Butyl Ricinoleate(called Ricinolsihrebutylester 193.24, N 7.25%. Several isomers are known and
in Ger), C1~H3303C4H9; mw 354.56, 0 13.54%; described in the literature: 2-Nitro-4-(see-butyl)
yel to COI liq, bp 275° at 13mm, fl p 220°, - toluene(R ef 5); 2-Nitro-4-(tert- butyl)-toluene
d 0.x6 at 22 °(Refs 1,2,4 & 5); was first prepd (Refs 2 & 4); 5-Nitro-3-(tert-butyl)-toluene(Refs
by Walden(Refs 1 & 2) from ricinoleic acid, butyl 1 & 3); and 6-Nitro-3-(t ert-butyl)-tolu eneRef 1)
alcohol & HC1. It was proposed as a deterrent Refs: l)Beil 5,438 2)Beil 5, [334] 3)B.M.
surface agent for progressive burning proplnts Dubinin & N. E.Kozhevnikova, ZhObschKhim
(Ref 3). Because butyl ricinoleate is a non-solv 21, 662(1951) & CA 45,9500(1951) 4)M..5.
for NC, but compatible with it, the coating does Carpenter, JOC 16,587(1951)& CA 46,1491(1952)
not penetrate the proplent grains during prolonged 5)N.M.Cullimane & D.M.Leyshon,J-CS 1954,2947
storage, as do some other coating compds & CA 49, 12324(1955)
Re/s: l)Beil 3, 38 8,(138) 2)P.Walden,Ber 36, Dinitrobutyltoluene, C4H9 .C6H2(N02)Z.CH3; mw
782( 1903) 3 )H.M.Spurlin & G. H. Pfeiffer,USP 238.24, N 11.76%. .TWO isomers ~e known:
2187866(1940) & CA 34,3918(1940) 4)Sax(1957), eso-Dinitro-3-(’tert-butyl)-toluene, ndls, mp 92°, bp
411-12 5)CondChemDict( 1961),189 ca 224-5°(in vacuo)(Refs 1 & 3) ~d 2,6-Dinitro
 B 389

-4-(tert-butyl)-toluene, grn-yel lfts(from diI al c), Re/s: 1 )Beil-not found 2)US Rubber Co, Quarterly
mp 94-5 °(Refs 2,4,5,6 & 7). Other props & Progress Rept No 10, Contract Nerd 10129,
methods of prepn are given in the Refs Passaic, NJ(1950), 20
Refs: l)Beil 5,438 2)Beil 5,439,(210)& [334]
3)A.Baur, Ber 24,2835(1891)& Ber 27,1624(1894) 2. Butyl-(l,l,l-trinitro-n-propyl)-ether,,
4)M.Battegay & P. Haeffely, BuIIFr 35,985(1924) & (0,N).C.$H.CH3; mw 251.20, N 16.73%; liq; bp
CA 19,43(1925) 5)H.Barbier, 14-me Congr?s de 0.C4H9
Chimits Industriele, Paris 1934,4pp(Oct 21-7) and 76° at lmm, n~ 1.441o at 200; was.prepd by
CA 29,5821(1935) 6)M.S. Carpenter & W.M. Easter, interaction of nitroform acetaldehyde(or paral-
JOC 19, 87(1954)& CA 49,3044(1955) 7)N.M. dehyde) and n-butanoI(Ref 2~ Its expl props were
Cullinane & D.M.Leyshon, JCS 1954,2947 & CA not reported
49,12323(1955) Re/s: l)Beil - not found 2)US Rubber Co,
Trinitrobutyltoluene, C4H9.CGH(N02)3. CH3; mw Quarterly Progress Rept No 10, Contract Nerd
283.24, N 14.84%. Three i Somers are described 10129, Passaic, NJ(1950),P 8 and Table 1
in the Literature: 2,4,6 -Tn”nitro-3-(n-butyl)
- toluene, greenish ndls(from ale), becomes red and
then yel-bm or exposure to light; mp 78.5°; was
prepared by nitrating 3-butyltoluene at 10-20° N-Butylurethane and Derivatives
(Refs 3 & 6); 2,4,6- Tn”nit~-3-(iso- bufyl)-tol~ene, N-Butylurethane or Butylethylcarbamate( called
crysts(from dil ale), having an odor resembling Butylurethan or Butyl-carbamidsaureathylester in
that of musk, mp 124°; was prepd by nitrating Ger), C4H9.NH.CO0.C2H5; mw 145.20, N 9.65%.
m-iso-butyltoluene( Refs 1 & 5); and2,4, 6- Trirzit~o The Four isomers: N-(n-Butyl}urethane( Ref 1);
-3-(tert-butyl)-toluene, lt yel ndls(from ale), having N-(see-Butyl).uretbane(Ref 2X N-{iso-ButyI)
an odor of musk, mp 96-7°; readily SO1 in ~c, eth~ -urethune(Ref 3~ and N-(tert-Butyl)- uretharze
chlf, benz & petr eth; insol in w; was prepd by (Ref 4) are described in the literature
nitrating m-tert-butyltoluene( Refs 2,4,6 & 7). Refs: l)Beil 4,158 & (371) 2)Beil 4, 162 &
Other props & methods of prepg the trinicro derivs [636] 3)Beil 4, 168& [640] 4)Beil 4,174&
are given in the Refs. Their expl props were not (377)
investigated
Re/s: l)Beil 5,437 2)BeiI 5,438 3)Beil 5, [333] N-Nitroso-N-(n-butyl)-urethane, C4H9.N(NO).C00.-
4) A. Baur:B er 24, 2836-7(1891) 5) E. Knoevenagel~ C2Hg; mw 174.20, N 16.08%; red oil, bp-explodes
Ann 289 ,165(1896) @R. DeCapeller* HeIv 11* when attempts are made to distill it; was prepd by
166-72(1928) & CA 22,1339(1928) 7)A.V. Grosse nitrosation of N-(n-buryl)-ureth ane( Refs 1,2 & 3)
et al, JOC 3,448-55(1938) & CA 33,21 12(1939) Refs: l)Beil 4,(372) 2)S.Nirdinger & S. F. Acree,
2,4,5,6.Tetranitro-3-(tert-butyl)-toluene(?), AmChemJ 43, 380(1910) & CA 4, 1616-17(1910)
C4H~.C6(N02)4.CH3; mw 328.24, N 17.07%; pale 3)A.L.Wilds & A.L.Meader Jr, JOC 13,771(1948)
ye} plates(from MeOH), mp 222°; was .obtd Mononitrobutylurethane, C4H9 .N(N02).CO0.C2H5;
. bY
vigorous nitration of Mosken e, [ 2,6-dmcro-3-(tert mw 190,2Q N 14.73%. Four isomers are described
-butyl)-4-(iso-prophy l)_toluene], with mixed acid in the literature: N-Nitro-N-(n-buty l)-urethane,
and oleum at 115°(Ref 2). Its expl Props were not Iiq, fr p below -70°(Ref 1); N-Nitro-N-(see-butyl)
investigated -urethane, Iiq, fr p below -70 °(Ref 1); N-Nitro-N
Refs: l) Beil-not found 2)M.S.Carpenter & W“M” -(iso-butyl,)-urethane, Iiq,fr p below -75°(Ref I);
Easter, JOC 19, 100(1954) & CA 49,3045(1955) and N-Nitro-N-(tert-butyl)-urethane, liq, bp 56° at
2mm(dec), d 1.051, n~ 1.4331 at 20°; UV spectra
N-Butyl-toluidine. Same as N-Butyl-aminotoluene detd(Ref 2); was prepd b; nitrating N-(tert-butyl)
-urethane with fuming HN03 & acetic anhydride
n-Butyl-4,4,4-trinitrobutyrate, (02 N)3CWCHZOCHZ*- ( Ref 2). .No expl props were reported for these
COOCAH9; mw 279.21, N 15.05%; liq~ bP 107-80 at nitro compds
ca 0.4mm, n~ 1.455o at 200. Was prepd from Refs: l)Beil 4,159,163 & 172 2)H.M.Curray &
nitrofotm and n-butyl acrylate in n-butanolic soln, J. P. Mason, JACS 73, 5043-45 & 544Y50(1951}
as described in Ref L Its expl props were not detd CA 46, 9442(1952)& CA 47,497( 1953)
 I

Butylxylene and Derivatives 4)H.A.Bruson, “Preparation of Polymers which

Butylxylene or Butyldimetbylber.zzene( called Butyl Might Be of Intrest in Explosives”, NDRC Div 8
-xyloI or Butyl-dimethyl-ben zol in Ger), C4Hg.- Irrterim Rpt PT~7, p 25(1943) 5)C. JO Teahan,
CGH3(CH~)2; mw 162.26, H 11.18%. Three USP 2377727(1945) & CA 39, 4092(1945)
isomers are described in Beil 5,477,(213) & [ 339] Teahan,USP 2377727(1945) & CA 39,4092(1945)
Mononitrobutyhty lene, C4H9.C6H2(N02)(CH3 )2; [Purification of trinitro-(tert-butyl )-m-xylene]
mw 207.26, N 6.7%. Two isomers are described in 6)H.Brockmann & F.Volpers,ChemBer 80,77-82
Beil 5, 447 & [ 339] ( 1947) & CA 41 ,3071 (1947 )( Chromatographic
Dinitrobutylxylene, C4H9.C6H(N02)2( CH3)2; mw separation) 7) R. C. Fuson et al$JOC 12,587(1947)
252.26, N 11.11%. Two isomers are known: &’ CA 41 ,7386( 1947)(Structure of musk xylene and
5-(tert-Butyl)-2,4 -dinitro-m-xylen e, yel ndls(from others) 8)P. Fielding & R. J. W.-LeFkvre, JCS
ale), mp 68°; readily sol in org solvs(Refs 1,3 &4~ 1950,2812 & CA 45,2775 (1951)(UV spectra) 9)F.
and 5-(tert-Butyl-4, 6-din itro-m-xylene, plate s(from Carter, Perfumery & EssentOil Record 43, 296,312
Iigroin) or ndls(from ale), mp 84°(Refs 2 & 3). (1951) & CA 46,1718( 1952)( PiIot plant studies)
Other props & methods of prepn are given in the 10)K.Kawasaki,Koryc( Aromatics) No 19, 33-5
Refs Ii steal (1952) & CA 46,7288( 1952)(Methods of prepg
Re/s: l)Beil 5, 447 & [339] 2)Beil 5,448 3)A. various musks & musk derivs) ll)K.Kawasaki &
Baur, Ber 33, 2565-66(1900) 4) H. Barbier,Helv K.Mihara, J SocOrgSyntheticChem(J span) 10,
11,159(1928) 259-63( 1952) & CA 48,1 1368( 1954) 12)V.M.
2-Azido-5-(tert-butyl).4,6-dinitro-m-xylene, Rodionov et al, ZhObshchKhim 23, 1802-8(1953)
C4H9.CG(N3)(N02 )2(CH3)2, mw 293.28, N 23.88%; & CA 49,896(1955) 13) D. V. Nightingale & J .M.
wh lfts with odor of musk(from ale), mp 146°; Shackelford,JACS 76,5767-70( 1954) & CA 49,
insol in w; sol in common org solvents. Can be 14656(1955 ) 14)V.V.Serpinskii et al, ZhFizKhim
prepd by the action of ammonia on the p erbromide 30, 177-83( 1956) & CA 50, 10468( 1956)(Vapor
of diazoti zed 4,6-dinitro-2-amino- 1,3-dimethyl-5 pressure data at RT)
-terr-butylben zene. Its expl props were not detd
Re/s: l)Beil 5, 448 & [340] 2)P.Fisch, La 3-Butyn-l-yl-p-toluenesulfonate, H<–C(CH3)=CH
P arfumerie Modeme 12, 129-33(1920) & ChZtr HC-C - &H ;
93 II, 271( 1922) +0,.0.CH2.C;CH
Trinitrobutylxylene, C4H9.C6(N02)3(CH3 )2; mw mw 224.28, Iiq, bp 90° at 10-4mm; SI decopn at
297.26, N 14.14%. The following isomers are known 128° & O.Olmm and expl decompn when distn was
and described in the literature: 2,5, 6- Trinitro-4 attempted at 0.5mm; n~ 1.5262 at 19°; was prepd
-(n-butyl)-m-xy lene, ndls(from ale), mp 91 °(Ref 4) by slowly addg 3-butyn-l-ol (HC~C.CH2.CH20H)
(See ako Refs 11 & 13); 2,-5,6-Trinitro-4-(see to a soln of toluene-p-sulfonyl chloride
-butyl)-m-xylene, ndls(from ale), mp 107°(Ref 4) ~H9.CGH4S02C1) in pyridine at a temp below
(See also Refs 11 & 13); 2,4,6-Trinitro-5-(see 25°
-butyi)-m-xylene, fibers(from ale), mp 97°(Ref 4) R e/s: l)Beil-not found 2)G. Eglinton & M.C.
(See also Refs 11 & 131 2,5,6-Trinitro-4-(see Whiting, JCS 1950, 3653 & CA 45,7053(1951)
-butyl)-m-xylene, ndls(from sIc), mp 112 °(Ref 4);
and 2,4, 6- Trinitro-5-(tert-bu tyl)-m-xylene, ndls Butyramide and Derivatives
( from ale), mp 113°(stable form) and 105-6° Butyramide, Butyric Amide or Butanamide(called
(labile form)(Ref l)(See also Refs 23456789 >>>>>t!> Butyramid, Butters5ureami d or But anamid in Ger),
10,11,12,13 & 14). Other props and methods of C4H9.C0.NH2; mw 87.12, N 16.08%. Two isomers
prepn are given in the Refs listed are described in Beil 2,275,293,(122,129), [251,
Bruson(Ref 4) claimed that on treating 262] & {616,654}
2,4,6-trinitro-5 -(tert-butyl)-m-xy lene with Azidobutyramide, C4H8N40; 128.14, N 43.73%.
form aldehyde, it is possible to introduce two Two isomers are known: 2- Azido-n-butyric-l-ami de,
methylol groups which on nitration yields a CH3.CH2.CH(N~). C0.NH2, ndls(from benz+
D initrute deriv, C ,2H1 ~Ns012 of possible value petr eth), mp 38-9°(dl-form) & ndls(from benz),
as component of proplnts and expls mp 59°(1-fotm); and 2-Azido-iso-b~typ~-um ide 07
Refs: l)Beil 5, 448,(213) & [ 340] 2) S. H.Katz 2-Azido-2-methyl-propion-l-amide, (CH3)2C(N~).-
and E. J. Talbert, BurMinesTechPaper 480,37pF C0.NH2, rectangular pltlts, mp 93-4°. Other props
(1930) and CA 25,547(1931) 3)D.V.Nightingale & & methods of prepn are given in Refs 1 & 2
L. I.Smith, JACS 61 ,103(1939) & CA 33,1681(1939) Re/s: l)Beil 2,287,299 2)M.D. Forster & R.
 B 391

MiilIer,JCS 95 i, 194,196,197(1909) thrown on a hot plate(Refs 2 & 4); and 4-Azido

2-Nitmso:iso-butyramide, (CH~)2C(NO).C0. NH2; -butyric Acid, N~.CH .CH2.CH2.COOH, yel oil,
m w 164.16, N 17.07%; prisms(ftom boiling w)> mp fr p below 0°, bp 1353 at llmm; readily sol in slc
ca 158°(dec); was prepd by treating a-nitroso-iso or eth; less sol in w; its Na salt, C4H6N302Na,
-butyronitrile with coned HCI at OO. Other props crysts(from dil ale), dec ca 205 °(Refs 3 & 5).
are given in the Refs 1 & 2 Other props & methods of prepg azidobutyri c acids
Re/s: l)Beil 2,298 2)0.Piloty & B. G. Schwerin, are given in the refs listed
Ber 34,1865-66(1901) & JCS 801,5 16-17(1901) These isomers form Iiq, Azidobutyryl Ethyl
2-Nitm-iso-butyramide, (CH3)2C(NO~.C0.NH2; Esters, N3.C3H6.COz.C2H~
mw 132.12, N 21.20%; lfts(from eth), mp 117-18°; Re/s: I)Beil 2,287 & [257] 2)Beil 2,299
mod sol in w or ale; less sol in eth; decompd by 3)Beil 2,(126) 4)M.O.Forster & R. Miiller, JCS
heating in, dil H2S04; other props & methods of 95 I, 193,195 & 196(1909) 5)T.Curtius & W.
prepn are given in Beil 2,299 & (130) Giulini,Ber 45,1047 & 1048(191 2); JCS 102 I,
Dirzitrobutyramide, C3H~(N02)2.C0.NH2; not 427(1912) & CA 6, 2433(1912) 6)W.F.Huber,JACS
found in Beil or in CA thtu 1956 77, 112(1955) & CA 50,804(1956)
Trinitrobutyramide, C3H4(N02)3.C0.NH2; mw Butyric Acid Azide or Butyryl Azide,
222.12, N 25.23%. .An expl compd called C3H7.C0.N3; mw 113.12, N 37115%. Only one
4,4,4(or y)- Trirzitrobutyramide, (02 N)3C.C142.CH2. isomer is known: iso-B utyryl Azide, (CH3 )2 CH.C0.-
C0.NH2, was prepd by treating a meth snolic soln Na, wh cottagecheese like ppt, very unstable
of acrylamide with nitroform, as described in even in its ethereal soln; the f~eshly prepd
Ref 2; wh shiny pltlts(from water), mp 95-7°. It compd decomposes vigorously with evolution of
detonated relatively easily and burned vigorously gas when heated in a tube; was prepd by treating
R efs: l) Beil-not found 2)US Rubber CO @afierly iso-butyrl hydrazide with HC1 & a NsN02 soln
Progress Rept No 5, Contract Nerd 10129, Passaiq cooled with ice(Refs 1 & 2)
NJ(1948-49), 20-1 Refs: l)Beil 2, {656} 2) T. Curtius & O. Hambsch,
JPraktChem 125,185(1930)& BrA 1930A,755-56
Butyric Acid and Derivatives 4-Azidobutyryl Azide, N3.CH2.CH2.CH2.C0 .N3;
Butyric Acid, Butanoic Acid or Ethylacetic Acid mw 154.14, N 54. >3%; yel oil, bp-expl when
(called Butters aure. Propan-cabon s~ure or heated; was prepd by the reaction of the
xthylessigs~ure in Ger), C3H7.COOH; mw 88.10, hydrochloride of 4-azidobutyryl hydrazide with
0 36.32%. Two isomers are known: n(or u)-Butyric NsN02 & H2S04 in the presence of ether(Refs 1 &
Acid, CH3.CH2.CH2.COOH and /3(or iso)-Butytic 2)
Acid, (CH3)2CH.COOH Re/s: l)Beil 2,(126) 2)T.Curtius & W. Giulini,Ber
Refs: l)Beil 2,264,288(115,126), [235,257] & 45,1049(1912) & JCS 102 1,427(1912)
{637 } 2)*x(1957),414 & 7, 6 3)CondChemDict Butyric Acid Hydrazide or Butyryl Hydrazide,
(1961),190 & 623 C4H10N20; mw 102.14$ N 27.43%. ,Two isomers
Azidobutyric Acid, C4H7N~02; mw 129.12, N are known: n- Butyryl Hydrazide, C3H7.C0.NH.NH2,
32.55%. The following isomers are known: wh hygr ndls, mp ca 44°, bp 138° at 20mm & 120°
2-Azido-butyric Acid, CH3 .CH2 .CH(N3).COOH, at 10mm; readily sol in w, alc or eth; it forms a
COI ndls, mp 23.5°, ewl mildly when thrown on a Hydrochloride salt, C ~ H , 0N20 . HC1, wh trysts,
hot plate; bp 81° at 0.17mm, d 1.1519 at 33°; tie mp 148 °(Ref 1); ~d iso-B~tyryl Hydrazide,
Iiq rapidly attacks the skin(cll-form); its Ag salt, (CH3)2CH.C0.NH.NH2, wh ndis(from eth-ale) or
C4H6N302Ag, lustrous, transparent plates(from w) lfts(thru sublimation), mp 104; readily sol in w or
becomes violet on exposure to light; deflagrates ale; sl sol in boiling eth; it forms a Hydrochloride
when thrown on a hot piate; 2-Azido-buty~’c Acid salt, trysts, mp 122°, very bgr; and a picrate
(1-form),prde yel oil; its B~cine salt, C4H7N302 + salt, C H N O . C6H3N307, yel nd.ls(from w),
C23H26NZ04 + 4H20, COI ndls(from w), mp 131°, mp 144g(i~f ;)
dec on heating above mp(Refs 1, 4 & 6); 2- Azido See also Refs 3 & 4 for methods of prepg butyryl
-iso-butyric Acid or 2- Azido-2-metbjlp ropionic hydrazides
Aa”d,(CH3)2C(N3 ). COOH, lustrous ndls, mp 31°, Re/s: l)Beil 2,276 2)Beil 2,294 & {656} 3)K.
bp 75° at 0.15mm, expl mildly when thrown on a Satake & T. Seki, Kagaku no Ry6iki(JJ apchem) 4,
hot plate, d 1.1433 at 33°; it S1OW1Yproduces 557( 1950) & CA 45,4604(1951) 4)C.Ainswortil,
irritating blisters on the skin; its Ag salt, J ACS 76,5774(1954) & CA 49,14639(1955)
C4H6N302Ag, coi ndls(from w), detonates when 4-Azidobutyryl Hydrazide, N3.CH2.CH2.CH2. C0.-
 I

B 392

NH.NH2; mw 143.15, N 48.93%; yel gelatinous butyric Acid”, NavOrdRept 4437( 1956)(Cong, not
mass; was obtd by adding HC1 to a cooled used as a source of info)
ethereal soln of isopropylidene-4-azidobutyryl Trinitrobutyric Acid, Derivatives. The Methyl
hydrazide; the latter prepd by warming hydrazine Ester, (02 N)3C.CH2. CH2. C0.CH3, mw 237.13,
hydrate with 4-azidobutyric acid ethyl ester N 17.72%, is CO1 Iiq, bp 101-3 at 2mm, n~
foHowed by treating with acetone 1.4592 at 20° which burns rapidly in a flame. it
Re/.s: l)Beil 2,(126) 2)T. Curtius & W. Guilini, Ber was prepd by interaction of nitroform and methyl
45,1049(1912) acrylate(Ref 1). Ville(Ref 3) prepd an explosive
Mononitrobutyric Acid, C4~!7N04; mw 133.10, N compd Trinitroetbyltn’rzitrobutyrate(TNEtBu),
10.52%. Only one isomer is described in the (02 N)3C.CH,.CH2.C00 .CH2.C(N02)3; mw 386.16,
literature: 2-Nitro-iso-butyric Acid or 2-Nitro-2 N 21 .76%, mp 93-4°, by interaction of trinitro-
-rnethylpropiorzic Acid, (CH3 )2 C(N02).COOH, butyryI chloride, (02 N)3C.CH2. CFT2. COCl with
cysts, mp 950; readily sol in alc or eth; mod SO1 trinitroethanol, HO, CHZ. C(N02)3 in anhydrous
in hot chlf; S1 sol in w; v S1 sol in CS2; dec on benzene with small amt of coned H2S04. Expl &
prolonged heating & by heating with w, xylol or other props of TNEtBu are described in conf Ref 2
nitrobenzene it forms a blue oil(Refs 1 & 2). Re/s: I)US Rubber Co, Quarterly Progress Rept
Other props & methods of prepn are given in the No 4, Contract Nerd 101 29(19@), 6-7 2)0.E.
Re/s: l)BeiI 2,(129) & {662} 2) W. Steinkopf & Sheffield, {’Properties of Explosives of Milita~
A.Supan,Ber 44, 2893,2896(1911) Intrest”, PATR 1740, SUppl No 1(1958), 459-63
Dinitrobutyric Acid, C4H6N20G; mw 178.10, N (Conf)(Not used as a source of info) 3)J.Ville,
15. 73%. The dinitro derivs of butyric acid were MP 42, 25-6(1960)
not found described in the literature. Klager(Ref
2) prepd & described the aci-Na salt of Methyl-4,4 Butyric Acid Azide. Same as ButyryI Azide
-din itrobutyrate, ~O~Na
02N.C.CH2.C112. COOCF13, Butyric Amide. Same as Butyramide
bright yel trysts; and the Di-Na salt of 4,4
-Dinitrobutyrate, ~02Na Butyric Anhydride(called Buttershreanhydrid in
02 N. C, CH2.CH2.COONa, Ger), CeH1 ~03; mw 158.19, 0 30.34%. Two
yel crysts(from MeOI1), mp 97 °(dec). Later, isomers are described in the literature: N- Butyric
Klager(Ref 2) patented the prepn of the Na salts Anhydride, (CH3 .CH2. CH2.CO)20, clear li q, fr p
of methyl, ethyl & butyl esters of 4,4-dinitrohutyric -75°, bp 199.5°, flash p 1900 F(CC), d 0.9681 at
acid. These and other Na salts of poly nitro 20°; other props & methods of prepn are given in
compds or nitrated new aliphatic compds were Refs 1,3,4,5,6 & 7; and iso-Butyric Anhydnde,
proposed as expl ingredients because of their [( CH3)2CH.COI 20, liq, fr p ca 56.4°, boiling
uniformity & re~ative stabiIity range 180-87°, d 0.951 -o.956 at 20°; other props
Re/.s: l)Beil-not found 2)K.Klager, JOC 16, & methods of prepn are given in Refs 2 & 7.
162-3(1951) & CA 45, 6576(1951) 3) K. Klager, These compds are used in the synthesis of
USP 2640072(1953) & CA 48,7626-27(1954) various buryrates, drugs and t arming agents
Trinitrobutyric Acid, C4H5N’30~; mw 223.10, N Re/s: l)Beil 2,274,(122) & [251] 2)Beil 2,
18.83%. Its isomer 4,4,4(oT y)- TrirritrobutyriE Acid, 292,(128), [262] & {653} 3) G. E.Smith & W.
(02 N)3C.CH2.CH2.COOH, wh ndls, mp 62-3°, was Hunter, BritP 606607(1948) & CA 43, 3839(1949)
prepd at the lab of US Rubber Co(Ref 2) by 4)H,J.Hagemeyer Jr, USP 2476859(1949) & CA
refluxing a suspension of 4,4,4-trini trobutyramide, 43,8398(1949) 5)G.E.Smith & W.Hunter, USP
(02 N)3C.CH2.CH2.C0 .NH2 in aq HC1. It was also 2492403(1949) & CA 44,4925(1950) 6)Sax(1957),
prepd by Dacons as described in conf Ref 3. The 414 7) CondChemDict(1961 ),190,623
expl props of trinitrobutyric acid are not described
in Ref 2. Its silver slat, prepd by treating the Butyroloctone - a - corbonyl Azide(called
acid with Ag nitrate(Ref 2) is a mild expl, fairly Butyrolacton-a-carbons2ureazid in Ger),
insensitive to friction $H2. CH2$H.CON3; mw 155.11, N 27.09%; yel
R efs: l)Beil-not found 2)US Rubber Co, Quarterly o co
Progress Rept N6 7, Contract Nerd 10129, oil, expl violently when heated rapidly; was prepd
Passaic, NJ(1949), 10 3) J. C. Dacons et al, by the action of HN02 on butyrolactone-a
“Improv ed ‘One Pot’ Processes for Preparation -carboxylic acid(Ref 2)
o f 4 ,4- Dinitropimelic Acid and 4,4,4-Trinitro- R e~s: l) Beil-not found(The parent compd,
 B 393

butyrolactone-a-carboxy lic acid, is described in KCN(Refs 3 & 7X 4-Nitro-butymnitriZe,

Beil 18, 370) 2) T.Curtius & H. Sauerberg, 02 N. CH2.CH2. CH2 .CN, COI liq, having SI odor
JPraktChem 125,141,147(1930) & CA 24,3215(1930) & sharp sweet taste; ~p 236 °(dec), 160° at 35mm
or 1 lg-210 at 3mmjreadily sol in ale, eth, chIf or
Butyrone, Diprapyl Ketone or 4-Heptanone [called alkalies; insol in w. was prepd from 4-iodo-
Heptanon-(4), Dipropylketon or Butyron in Ger] , butyronitriI e and AgN03 or by other methods(Refs
C3H7.C0.CaH7; mw lI+f.18, O 14.01%; CO1 Iiq, 1 & 6); 2-Nitro-isobuty ronitrile or 2-Nitro-2-rnetbyl
fr p -32°, bp 144°, flash p 49°, d 0.8162 at 20°, -propion-i-nitrile, (CH3)2C(N02).CN, ndls(from
n~ 1.4068 at 20 °(Refs 1,2 & 3). Other props 8r Iigroin), mp 35°, bp 97° at 45mm or 73° at 12rnm;
methods of prepn are given in the Refs. It is used dec at 110-1 2°; readily sol in ale, S1 sol in w
as a SOIV for NC, raw & blown oils, resins & was obtd from 2-nitroso-i so-butyronitrile by
lacquers(Ref 3) rem aining in a wet condition or by treating with
Refs: l)Beil 1, 699(359), [754] & { 2857} 2)Sax coned HN03; and by treating a-hydroxylamino
(1957),409 3)CondChemDict( 1961,415 -i so-butyronitrile with a SU1furic acid-KMn04
soln at 30 °(Refs 2 & 5); and 3-Nitro-iso-buty-
Butyronitrile and Derivatives ronitn”le, 3- Nitro-2-metbyI- propion-l-nitrile or
Butyrorzitrile, Batanenitr-ile or Propylcyanide 3-Nitro-2-cYano-propane, 02 N. CH2.CH(CH3).CN,
(called Butyronitril,Butanrritril or Propylcyanid in Iiq, bp 68-700 at 0.5mm; was prepd by adding
Ger), CH3.CH .CHZ.CN; mw 69.10, N 20.27%; CO1 ~-nitroprop-i-ene in alc to an aq soln of KCN at
liq, fr p -11L6%, bp 116-118°, d 0.0796; sol in sIc -5 to O“(Refs 4 & 7)
or eth; SI sol in w; other props & methods of These compds are us efuI as intermediates
prepn are givem in Ref I. It is used as a basic in the manuf of expls, dyes & pharmaceuticals
material or intermediate for industrial chemicals or Re/s: l)Beil 2,287 & {636} 2)Beii 2,299 & (130)
pharmaceutical products(Ref 2) 3)Beil 2, { 636} 4)Bei~ 2, {662} 5)W. Steinkopf
Re/s: l)BeiI 2,275,(123), [252] & {618} 2) & A.Sup~ Ber 44,2895(1911) 6)0. Wulff et ~,
CondChemDict(1961 ),191 GerP 728531(1940) & CA 38,376(1944) 7)G.D.
4-Azido-butyronitrile, N3.CH2.CH2. CH2.CN; mw Buckley et al, JCS 1947,1501,1502; USP
110.12, N 50.88%; liq, bp 55-600 at >mm; was 2428614(1947) & CA 42,770(1948)
prepd by heating 4-chloro-butyroni trile with NaN3; Dinitrobutyronitrile, C4H5N304; not found in
when this compd is treated with chlorosulfonic Beil or in CA thru 1960
acid(Cf S03H) in chlf or with coned H2S04 in Trinitrobutyronitrile, C4H4NA06; mw 204.10, N
CC14 at 20-40°, Trirnethylenetetrazole is fo~ed 27.45%; not found in Beil or in CA thru 1960. The
(Refs 1 & 2) attempt ed prepn of 4,4, 4- Trinitrobutyronit n”le,
Refs: l)Beil 2,{ 636} 2) C. Gy~gyszer, GerP (02 N)3.C. CH2.CH2.CN, is described in Conf
611692(1934) & CA 29, 5994-95(1935); Usp Aeroj et Rpt 330( 1948),p 64. See also K.S. Warren,
2020937(1934) & CA 30,575( 1936) Doctoral Thesis, Purdue Univ( 1947)
2.Nitroso-iso-butyronitrile or 2-Nitroso-2-methyl
-propane-l-nitrile, (CH3)2C(NO).CN; mw 98.1O, N Butyrophenone and Derivatives
28.56%; CO1 solid, rep-begins to dec at 53° turning Butyrophenone, Butyrylberzzene, Pb enylbutanone
to a dk blue liq, and at 80° it evolves coi gas & or Propyl Pbenyl Ketone Butyrophenon,
[called
deposits trysts; was obtd by the oxidn of Buty rylbenzol, l-Oxo-l-phenyl-but an, l-Phenyl
a-hydroxylamino-i so-butyronitrile with Cl water -btuanon-(1) or Propylphenylketon in Ger] ,
at O“(Refs 1 & 3) or by treating a~a’-azov CH3. CH2.CH2. C0.C6H5; mw 148.20, 0 10.80%;
-isobutyronitrile with SnC12 in coned HCI at CO1 Iiq, fr p 11°, bp 228-229.5° at 760mm, d
20-25 °(Refs 2 & 4) 0.9967 at 25°; other props & methods of prepn are
R e~s: l)Beil 2,2.98 2)Beil 2, {662} 3)0. PilotY given in Beil 7, 313,(166) & [241]
& B. G. Schw.erin, Ber 34,1864,(1901)& JCS 801, Mononitrobutyrophenone, C2H5.CH2.C0.C6H4.-
516-17( 1901) 4)J.G.Aston & G. T. Parker> JACS Noz; mw 193.20, N 7.25%. The 2’-Nitro deriv,
56, 1387-88(1934) It yel oil having a sweet odor resembling that
Mononitrobutyronitrile, C4HGN202 mw 114,10, N of NB, VOI with steam; and the 3’-Nitro deriv, wh
24.55%. The folIowing isomers are known: brittIe pl ates(from ale), mp 61°; both were prepd
3-Nitro-butyronitrile, CH3.CH(N02 ). CH2 .CN, by Morgan & Hickinbottom(Ref 2) and listed in
straw colored liq, bp 81-2° at 0.5mm; was prepd Beil(Ref I). The 4’-Nitro deriv, trysts, mp 66-67°,
>y reaction of 2-nitroprop-l-ene with an aq so!n of was prepd by Sugimoto et al(Ref 3)
 1

B 394

Re/.s: l)Beil 7, [ 242] 2)G.T.Morgan & W.J. 1&2)

Hickinbottom, JCS 119 II, 1882-83(1921) 3)N. Re/s: l)Beil 2,( 122) 2) E. Ferrario,Gazz 40 II,
.%ginioto et al, JPharmSocJ span 71,1161(1951); 99(1910) & JCS 98 I, 707(1910)
CA 46,5011(1952) & JapP 1482(1954); CA 49,
11707(1955) Butyryl Peroxide. Same as Dibutyryl Peroxide
Mononitro-diazobutyra-phenone, C ,0 H9N303; mw
219.20, N 19.17%. The isomer, 4’-Nitro-2-diazo BUU. A cast double-base proplnt for rocket motors.
-butyropbenone or 4-Nitro-a-diazo-buty rophenone, The prepn & props are described in conf “Pro-
[ called l-p-Nitrobenzoyl-i-diazopropane by pellant Manual”, SPIA/M2( 1961),Unit No 619
Wilds & Meader(Ref 2)] C2H5.C(N2).C0.C6 H4.-
N02, yel ndls(from petr eth), mp 97.5-98 .5 °(dec); Buxton Test. A gallery test for “Permitted”
sol in ACOH with evoln of N; was prepd by expls conducted between WWI & WWII at Buxton,
reacting diazopropane in eth at -20° with England
p-nitrobenzoyl chloride(Ref 2)? The same compd Ref: Marshall 3(1932), 186-7
can be prepd by the method described by
Eistert(Ref 3), Buzane. Same as Bihydrazine
Re/s: l) Beil-not found 2) AtL.Wilds & A.L.
Meader Jr, JOC 13,. 774(1948) & CA 43,4653(1949) Buzylene(Buzylen in Ger). This term has,
3) B. Eistert,AngChem 61,186(1949) & CA 43, according to Ref 4, two meanings: a) The
6178(1949) biva lent radical - N: N. NH. NH- ad b)An
unisolated azohydroxylamine compd, HN:N.NH.NH2,
Butyryl Azide. See under Butyric Acid called isotetrazene or diazohydrazine. It has
been claime.~ that isotetrazene occurs in
Butyryl Hydrazide, See under Butyric Acid hippury~ phenyl-buzylene, C6H5 .N:N.NH.NH.CO.-
CH#-LC0.C6H.s(Refs 2,3,4)
Butyrylhydroperoxide. (Perbutyric or Peroxybutyric According to Ijofmann et al(Ref 3), the
acid)(called Butyrylhydropero~d or Perbutter- buzylene group is the same as the terrazene group
saure in Ger), CH2H~.CH2.C0 .O.OH; mw 104.10, 0 Re/s: l) Beil-not found 2) T. Curtiu s,Ber 26,1266
46.11%; liq, fr p -10.5” bp 26-3° at 12mm(72% (1893) 3)K. A. Hofm~n et fl,Ber 93,1087(1910)
concn) & 41-2° at 13mm(85-90% concn); expl on SI 4)Hacich’s(1946),152
heating; was prepd by reacting butyri c anhydride
with an excess of H=OO in the presence of Buzz Bomb. See Bombs, Buzz in this volume
H2S04(Refs 1 & 2). Other methods of prepn & props
are given in Refs BV-143. A Ger WWI.I guided subsonic missile of
the air-to-surface type
Re/s: l)Beil 2,(122), [215] & {613} 2)J.D.’Ans
W. Frey,Ber 45, 1850,1852,(1912; CA 6,2737-38 Re/: DictGuidedMissil es( 1959),106
(1912) & JCS 102 I, 601-2(1912) 3) F. Fichter &
BV-246, A Ger WWII guided missile of the
H. Reeb,Helv 6, 456(1923) & CA 17,3323(1923)
air-to- surf ace type
4) F. Fichter & A. Burgin,Helv 14,1OO(1931)
Re/: DictGuidedlvfissiles( 1959), ~06
Butyryl Nitrate(called Bwyrylnitrat or Saltpeter-
BW. Abbr for Biological Warfare. ,Se e under
s~ure-butt ersiiure-anhydrid i n Ger), CH3.CH2.CH2.-
Chemical, Biological and Radiological(CBR)
C0.0N02; mw 133.10, N 10.52%; It Yel liq, mP
Warfare
detonated when heate~ was prepd by reaction of
butyryl chloride ‘with AgNOa at IOW temp(Refs 1 &
BWC. Brit abbr for “board wood cellulose” which
2)
is obtained from Pinus Radiata [t contains ca
R e~.s: l)Beil 2, 274 2) F. E. Francis, Ber 39,3800
85% of a-cellulose
(19o6) & JCS 921, 53(1907)
Re/: H. A. Aaron son, Dover, NJ; private communic~
tion( 1960)
Butyryl Nitrite(called Butyrylnitrit or Salpertig-
s sure-butters~ure- anhydri d in Ger), CH3 .CH2.-
CH2.C0.0NO; mw 117.10, N 11.96%; yel iiq,
bpdec on heating between 70-80°; was prepd by
action butyryl chloride on AgN02 at 30-40°(Refs
 cl

C(Explosifs)(Explosifs de mine type C). Re/: PATR 251O(PB 161270)( 1958),p Ger 23
Mining expls manufd in France beginning
ca 1895 and designated in Fr as: a) n“ia: C-4A An experimental double-base proplnt
AN 93 & Amm cresylate 7% b) n“lb: AN 78 prepd and investigated at CALTECH, Pasadena,
& Amm cresylate 22% and c) n02: AN 75 & Calif, during WWII: NC(12.6%N) 56.O,NG 43.o
Amm cresylate 25% & EtCentr 1%
Refs: l)A,Delatour,MP 10,57(1899-1900) Ref: L.Pauling et al, OSRD Rept 5967(1945), 11
2)DanieI(1902),90
C/68. An older Ger BkPdr, prismatic, with 7
C(Explosives). See Composition C, C-2, perforations and of low d
c-3 and c-4
C/75. An older Ger BkPdr, prismatic, with 1
C(Powder). A “coarse’’(large grain) BkPdr perforation and high d
formerly manufd by DuPont Co. Also CC
and CCC Powders C/77. An older Rus BkPdr, prismatic, with 7
Re/:Daniel(1902),90 perforations and of low d
Re/: Danie1(1902),651
C(Process). See “C” Process (Croning
Process of Precision Casting) ~88. A Ger designation for PA, which was
used for some time, begiming in 1888, for
filling projectiles
Cl (Poudre). A Fr BkPdr formerly used in
Ref: Daniel(1902),90
field guns
Ref: Daniel(1902),90
C/89. A Ger designation for a double-base
proplnt similar in compn to an Italian
C-2, A Ger guided missle of WWII, known as
Bailistite. It was also known as .RGP/89
Wasserfall
(Rauchloses”Geschutzpulver, 1889, which
Ref: Anon,’’Getmam Explosive Ordnance” ,TM
means Smokeless Gunpowder, 1889)
9- 1985-.2(1953),219-23
Ref: Daniel(1902),90-2

C2 (Explosive). According to Schwartz(Ref),

C-509 propel I ant. See conf Report by
it is a substance, closely related to TNT,
R .A.MiUer & J .E.Baldwin, NOTS(Naval
wifi an oily base. Workers exposed to
Ordnance Test Station) TP 2660(1962)
C2 regularly developed severe headache,
nausea, vomitting and occasional tremors CA, (Coton azotique l)(Fr). ColIodion cotton
of the upper extremities within a few hours contg ca 12%N and designed for use in
after exposure varnishes
12e/: A.M. Schwartz,NewEnglJMed 235,541
(1946) & CA 41 ,285(1947) CA2(Coton azotique 2)(Fr). Collodion
cotton contg ca 12%N and designed for
C-.2( Polvere). An Ital proplnt which was use in Blasting Gelatin(Dynamite gomme
manufd since ca 1910 by the societ~ Italiana in Fr)
Dinamite Nobel Avigliana. The compn used Re/: M. M. Kostevitch, Buenos Aires.
&ring WWII contd NC(mixt of collodion and Private communication(1955)
guncotton) 70, NG %, vaselin 5 & Na car-
bonate(or bicarbonate) 1%. ( see also Csp - 2) Cacao(or Cocoa) Powder. See Brown Powder
R ef: Anon, ordnance Serge~t,Aug 1943,P 17 under Black Powder Modifications

C2(Poudre). A Fr BkPdr formerly used in

Naval 65 and 90mm guns Cacodyl Cyanide or Dimethylarsenocyanide,
Ref: Daniel(1902),90 (CH3)2AS.CN; trysts, mp 36.5-37.5°. This
extremely toxic compd was first prepd by
C6. A Ger expl compn of WWII used as Bunsen(Ref 1). Expln of cacodyl cyanide cost
a substitute for TNT Bunsen the sight of his right eye(Ref 2)
 C2

Re/: l)Beil 4,6o8 & [988] 2) F. J. Moore, “A VO1 l,p A526-L

History of Chemistry”, McGraw- Hill, NY
( 1939), 267 Cadmium Azidodithiocarbonate. See
Vol l,p A636- R
CAD. Abbr for Cartridge Actuated Device
Cadmium Bromate. See under Bromates
Cadaverine and Derivatives
Cadaverine; 1,.5-Diaminopentan e; 1,5 Cadmium Chlorate. See under Chlorates
-Pentanediamine or Pentametbylenediamine,
H2N.(CH2)5 .NH2; syrup, mp + 9°. Other props & Cadmium Diammine Azide. See Vol 1,
prepn are in Beil 4, 266, (421)& [708] p A277,table A, item Cd 1
3,3- Dinitrocadaverine or 3,3-Dinitro- 1,5
-pentanediamine, H2N.CH2.CHz.C(N02 )2. CH2- Cadmium Diazide, See Vol l,p A526- L
CH2.NH2; mw 192.18, N 29.16%; CO1 c~sts
which become yel on exposure to the atm, mp Cadmium Fulminate. See under Fulminates
76- 9°; was obtained by mechanically shaking
3, 3-dinitrocadaverine dihydrochloride with the Cadmium Hexammine Bromate. See Vol 1,
theoretical amt of std NaOH soln for lhr. The p A277, table A, item Cd 5
dihydrochloride was obtained by refluxing
dimethyl. ,3,3- .dinitropentadicarbanate with coned Cadmium Hexammine Chlorate. See Vol 1,
HC1 for 16hrs. Expl props of dinitrocadaverine p A277, table A, item Cd 6
were not detd
R e/: l) Beil–not found 2) L. Herzog et al, JACS Cadmium Hexammine Perchlorate. See Vol 1,
73, 751(1951) & CA 45, 5609(1951) p A277,table A, item Cd 7

Note: C5H1 , N~06 Tetranitrocadaverine,

Trinitro-,
Cadmium H ydrazine Nitrate, Cd(NOa)2.3N2H4; wh
trysts, expl on rapid heating to ca 250° or
C5H, 0NG08 were not found in Beil or CA thru
on strong impact; when spread in a thin
1956
layer it bums with evoln of brn fumes;
Cadmium, Cd, at wt 112.4; soft blue- wh can be prepd by treating an aq (or alcoholic)
malleable metal or grayish- wh powd; d 8.642 at soln of Cd nitrate with redistilled
hydrazine hydrate, free of ammonia
17°, mp 320.9°, bp 767°; insol in w; sol in acids
Re/: L. MSdard & J .Barlot,MP 34,161- 4(1952)
and AN solns; occurs chiefly as greenockite
(CdS) associated with Zn(or Pb) manuf. Its & CA 48,6125( i954)
toxicity is discussed by Sax(Ref 3). Fire and
expln hazards are slight when Cd dust is Cadmium Iodate. See under Iodates
exposed to heat or flame(Ref 3)
Cd and some Cd salts were patented by Cadmium Nitrate. See under Nitrates
DeMent for use in smoke- producing
pyrotechnic compns (Ref 6) Cadmium Nitride. See under Nitrides
Re/s: l)Mellor 4(1923),420,457 & 472
2)Kirk & Othmer 2( 1948),716- 23 Cadmium Perchlorate. See under Perchlorates
3)Sax(1957),417 4)Gmelin,Syst Nr 33(1959)
~)CondChemDict( 1961),193 6)J .DeMent, Cadmium Permanganate. See under P erman-
ganates
USP 2995526(1961)

Cadmium Picrate. See under Picrates

Cadmium Acetylide. See Vol I,p A71- L

Cadmium Amide. See VO1 l,p A169- L Cadmium Selenide. See under Selenides
Note: According to Jacobson 2(1948),17,
Cadmium Sulfide. See under Sulfides
Cd(NH2)2expl on rapid heating above its
mp(180°)
Cadmium Tetrammi ne Bromate. See VO1 1,
Cadmium Azide. See Cadmium Diazide in p A277, item Cd 2
 C3

Cadmium Tetrammine Chlarate. See Vol 1, dissolvent” , abbreviated as poudres SD), the
p A277, item Cd 3 galette consists of a mixt of NC & NG(w/wo
DEGDN which is called N60 in Fr), impregnated
Cadmium Tetrammine Iodate. See Vol I, with w and compressed in a hydraulic press. For
p A277, item Cd 4 example, “galette 2-SD” consists of CP2SD
(coton-.poudre with N 11.7%) ca 72.7 & NG ca
Caes ium. See Cesium 27.3% impregnated with w. This galette is broken
up and blended in a~’malaxeur” with stabilizers
Caffeine and Derivatives -gel atinizers and other” ingredierks of proplnts, For
Caffeine or 1,3,7- Trimethyl-xantbirze( Kaffein example, the so. called “poudres ~paisses’ ‘SD-
in Ger), CeH10N402; mw 194.19, N 28.85%; 12, SD- 19 & SD- 21 contain: galette 2--SD ca 91,
CO1trysts, mp of anhydrous compd 234-5°. EtCentr 8.50-8.75 & vaselin 0.25- 0.50% with
Other props and prepn in Beil 26, 46I, (136) & O. l% graphite added(Refs 2,4 & 5)
[2661 Lhoste(Ref 6) and Parpaillon(Ref 8) de-
scribed rapid methods of analyses of various
8-Azidocaffeine or 1,3,7- Trimethyl -8 galettes and Miaud(Ref 7) described a method
-.azido- xanthine, C8H9N702; mw 235421, of detn of moisture content in galettes SD and in
N 41.69%; CO1 ndls(from ale), mp dec w/o woodpulps by means of high-frequency currents
melting; v S1 sol in w; was prepd by treating an R e/s: l)Pascal(1930), 204-5 2)J .Ch6din,MP 29,
aq soln of 8- hydrazinocaffeine hydrochloride 95- 11o(1939) 3)DavX1943),46- 7 4)G.Fleq.MP
with Na nitrite. Its expl props were not 30,236(1948) 5)A.Douillet,MP 30,303(1948) 6)P.
reported Lhoste,MP 37,149(1955) 7)P.Miaud,MP 37,465
R e/s: l)Beil 26, 477 2) L. Cramer, Ber 27, (1955) 8)M.Par’paillon,MP 40,217(1958)
3090(1894) 3)CA 1907-50, not found
Cake Powder, also called Mommotb or Rodman
g- .Nitroca/ feine or 1,3,7- Trimeth yl- 8- mitro Powder. See under BLACK POWDER or GUN-
- xarztirze, C8HQN504, mw 239.19, N 29.28%; POWDER, Historical
yel lfts(from w). Other props & prepn in Beil
26, 477 Caki ng(or Agglomeration) and Its Prevention.
Caking is defined in Hackh’s( 1944) ,p 156, as
Cahuecit. See Carboazotine {*the transformation of a powdered substance
into a solid mass either by moisture, heat or
Cahucit. Ger name for Cahuecit. See pressure”. The most common method of
Carboazotine preventing caking of a hydroscopic substance
is coating its particles wifi non-hydroscopic
Cake(Galette in Fr). The term galette is materials. Several methods and Refs on water-
used by the French in the manuf of BkPdr proofing AN crystals are given in Vol l,pp A334-
and smokless proplnts. The galette of L to A335- R under AMMONIUM NITRATE
BkPdr is described by Pascal(Ref 1) Following are some addnl Refs on pre-
and it is essentially the same as the vention of caking: l)A.Scott,USP 1811699(1939)
‘fpress - cake”, described by Davis(Ref 3) & CA25,5033( 1931 )( Caking of tryst substances
In the manuf of Fr smokless proplnts there such as used in chlorate expls can be prevented
are essentially two kinds of galettes. When by incorporating asbestos 5% or less of total
intended for the manuf of single-base(NC) wt) 2)Dynamit A- G,GerP 722144(1942) & CA 47,
proplnt, the galette consists of pulped, sta- 5241( 1943)( Caking of AN expls can be prevented
bilized NC(coton-.pou.dre in Fr) impregnated with by incorporating a small quantity of voluminous
w or alc and compressed in a hydraulic press. alumina hydrate) 3)R.C.CIogau, USP 2407151
The resulting galette, which is similar to the Amer (1946) & CA 41,286(1947) [Caking of AN, Na
block, is broken up and blended with a col- nitrate or other H20- sol granular materials can
Ioiding agent(such as ether- alc or acetone) and be prevented by coating the grains with a finely
a stabilizer(such as DPhA) in an apparatus divided(less than 1P in diam) Si compds
called “malazeur’’(mixer or blender) (such as CaSi04 or pptd Si02) in amts of 0.5- 5%]
When intended for use in the manuf of 4)J.Ordonneau, AnnMines(France) 139,35-63( 1950)
double- base solventless proplnts(’‘poudres saris & CA 44,6587(1950)(Caking of KCI trysts can be
 I

C4

reduced by coating them with paraffin waxes and thymus-nucleic or arabic] 12)H.Seifert,Chem-. Ing-
high- boiling petroIeum fractions) 5)’‘Monteca- Tech 27,135-42(1955) & CA 49,7152( 1955)(Dis-
tini’’SGlMC,ItalP 455258(1950) & CA 45,5352 cussion of the problem of crystal shape and its
(195 I)(Caking of hydroscopic materials, such as effect on caking and other props) 13)A.L.Shneer-
AN or kieselguhr can be prevented by coating son et al, ZhPriklKhim 29,743- 7(1956)(Engl trans-
their particles with H20- repellant substances, lation) & CA 51 ,6063 (1957 )( Caking characteris-
such as naphtha, melted paraffin or methyl chlo- tics of AN) 14)NV Koninklijke Nederlandsche
rosilanes) 6)T.V. Zabolotskii,ZhPriklKhim 23, Zouitindustrie,DutchP 83128(1956) & CA 52,7633
1203-.8(1950) & CA 46,8817 (1952) (Caking of AN ( 1958)( Caking of NaCl is reduced by coating its
is attributed to a polymorphic change at 32° to a particles with an aq soln of a Cd salt such as Cd
less- dense crystal structure and the sorption of chloride) 15)Ibid,DutchP 83383(1956) & CA 52,
w to form a satd soln on the surface from which 141 10( 1958)( Caking tendency of K sulfate, Amm
fine trysts separate by evapn to fill inter- sulfate or their mixts can be decreased by incor-
cryst spaces. The .lst cause can be eliminated by porating small quantities of an alkali dithionate)
the addn of foreign salts, particularly MgCl#H20, 16)G.Oyama et al, JapanP 9973(’56) & CA 52,
to the soln from which AN is being crystal. When 15853(1958)(Caking of hydroscopic N compds such
present in a concn of 3% of that of the AN, the as AN can be prevented by incorporating some Na
Mg salt is partly absorbed into the crystal lattice silicatd) 17)J .B .Rust & L. Spialter,USP 27 S8280
of the AN and forms rounded rather than needle- ( 1957) & CA 51 ,10974( 1957)( Caking of inorg & org
like trysts and eliminates transition at 32°. When granular hydroscopic materials can be prevented
this is followed by coating with a soln of paraffin by surface treatment with a Si halohydride or an
in anthracene oil to the extent of 0.4- 0.5~, the organosilicon halide in which the org radical is
caking is eliminated) 7)Y .Venkatesham, IndianP aliphatic or aromatic) 18)A.P.Milovanov et al,
41936(1951) & CA 46,1692 (1952 )(Caking of AN RUSP 105991(1957) & CA 51 ,15056 (1957 )( Caking
can be prevented by mixing it with powd ground- of AN in storage is prevented by adding to a soln
nut oil cake) 8)W.H.Rinkenbach, USP 2660541 of AN an extract obtained in the decompn of phos -
(1953) & CA 48,2301- 2(1954)( Caking of water- phorite with HN03. The soln is then neutralized
SOI salts can be partially prevented by coating with ammonia, vaporized, crystal and dried. As
the particles with a thin layer of water- insol vit- result of this treatment, the AN will contain 0,5-
reous materials consisting of a silicate, such as 2.5% p205) 19)M.Iwase,JapanP 6616(’57) & CA
Na- Al silicate. In the case of AN, its particles 52, 19289( 1958) (An addn of one or more of the con-
are sprayed with a suspension of hydrated alumina densation products of an aliphatic amine ~nd a
in aq Na silicate during agitation at a temp of 105- fatty acid or resin acid prevents the caking of
130°. Agitation is continued until the temp has urea, AN, NaCl & of other compds) 20) J. Ames,
dropped to ca 60°. As this process is conducted BritP 805112(1958) & CA 53,8557-8( 1959)( Normal
at elevated temp, the insol h-ydrated alumina re- aliphatic primary amines with at least 12 C atoms
acts with sol Na silicate to form an insol Na- Al or their salts as anticaking agents for AN) 21)
silicate coating. This coating, however, does M. Hoshikawa et al, JapanP 2866(’58) & CA 53,
not prevent the leaching of AN if the grains are 12530 (1959 )( Ethylenediaminetetracetic acid as an
placed in contact with moist materials, such as anticaking agent for urea, AN, Amm sulfate, etc)
the earth. This properry is desirable if AN is in- 22) P. K.Kovtun et al,RusP 109465(1958) & CA 53,
tended for use as a fertilizer) 9)H.13runel,FrP 19323( 1959)(A neutral non caking product is obtain-
58307(1953) & CA 52,18961(1958)( Al alginate as ed by treating AN with a small quantity of a metal
a coating agent) 10)A.M.Dubrovits kii et al, Zh- hydroxide and carboxylic acids or their mixt with
PriklKhim 27,349- 54(1954) & CA 49,15185(1955) unoxidized or partly oxidized paraffinic hydro-
(Engl translation)(Dendritic structure of AN carbons) 23)S.Varma et al, JSciIndResearch( India),
and its effect on caking) 1 l)Y.Ishikawa, J apanP 18 B,118- 22(1959) & CA 53,20660( 1959)( Gypsum
7593(’ 54) & CA 50,5950(1956) [Caking of hydro- as an anticaking agent for AN) 24)P .O.Marti,J r,
scopic materials can be prevented by treating USP 2901317(1959) & CA 53,22956( 1959) (Caking
their particles with a satd soln of AN contg a of AN particles is prevented by coating them with
small quantity of carboxymethylcellulose or other comminuted CUO or CU20) 25) R. R. Irani et al, IEC
substances, such as carboxyethylstarch o one of 51,1285- 8(1959) & CA 54,4072( 196t))(Study of
the organic acids(arginic, polyacrylic, PO[ yuronic, effectiveness of several common conditioners on
improving flow props and inhibiting caking) 26)
 C5

R. R. Burns,USP 2920937( 1960) &CA 54,7958 Calcium Nitride. See under Nitrides
(1960) (Caking of inorg salts such as AN, Amm
sulfate or borax is prevented by the addn of a Calcium Nitrite. See under Nitrites
small quantity of 1,2- substituted imidazolinium
salts) Calcium Oxide. See under Oxides

Calcinit(Calcinite). A Ger mining expl which ex- Calcium Perchlorate. See under Perchlorates
isted in several modifications. See PATR 2510
(PB 161270 )(1958),p Ger 23 Calcium Permanganate. See under Permanganates

Calcium, Ca, at wt 40.08; silvery- wh, soft metal Calcium Peroxide. See under Peroxides
which must be kept in tightly stoppered bottles; d
1, 578 at 15°; mp 810°; sublimes below its mp; Calcium Phosphide. See under Phosphides
sol in acids; decomposes water liberating
hydrogen gas. Can be prepd by electrolyzing Calcium Picrate. See under Picrates
molten Ca chIoride(Refs 1,2,3 & 5). Its toxicity
is discussed in Ref 4. Some of its salts were Calcium Plumbate. See under Plumbates
proposed for use in smoke producing compns
(Ref ‘6) Calcium Resinate. See under Resinates
Ref: l)Mellor 3(1923),626,631 & 637 2)Kirk &
Othmer 2(1948 ),744-5 3)Gmelin,Syst Nr 28(1950- Calcium Silicate. See under Silicates
I957) 4)Sax(1957,423-4 5)CondChemDict( 1961),
198 6) J.DeMent,USP 2995526(1961) Calcium Stearate. See under Stearates

Calcium Acetate. See Vol l,p A28- L Calcium Sulfate. See under Sulfates

Calcium Acetylides. See Vol I,p A71 Caliber is the diameter of the bore measured be-
tween opposite lands of a rifled smalI arm or an
Calcium Bromate. See under Bromates artillery weapon. The lands of a weapon are the
raised portions of the rifling in a bore, and the
Calcium Carbides. See Vol l,pp A71- R & A72- L spaces betw the Iands are called grooves
The diameter of small arms(which in the US
Calcium Carbonate. See under Carbonates includes all wea~ns whose bore is .6o inch or
less) is expressed in the US in hundredths of an
Calcium Chlorate. See under Chlorates inch, in Gt Britain in thousandths of an inch and
in all other countries in millimeters. The word
Calcium Chloride. See under Chlorides caliber(or the abbr Cal) is placed before the
number, such as Caliber .30(or Cal .30). The di-
Calcium Cyanamide. See under Cyanamide ameter of a bullet(see BULLETS) is always a few
thousandths of an inch greater than the caliber
designated
Calcium FIuoride. See under Fluorides The calibers of current US small arms are
listed in Vol l,p A386- L
Calcium Hydride. See under Hydrides For some firearms, such as shotguns, it is
customary to express the interior diameter as gage,
which is the number of spherical lead bullets, of
Calcium Hydroxide. See under Hydroxides the diameter of the gun bore, required to weigh
one pound. Thus, the bore measurements or shot-
Calcium Hypochlorite. See under Hypochlorites guns of popular sizes, standardized on above ba-
sis, are as follows (Ref 5):
Calcium Hypophosphite. See under Hypophos-
phite

Calcium Nitrate. See under Nitrates

 1

C6

Size of Gun Diam Size of Gun Diam simple, rapid method is described in Ref
Gage Inch Gage Inch Re/: Clift & Fedoroff, Vol 3, Chapter 2(1944),
8 0.835 .14 z p 33
10 0.775 16 0.662
0.729 20 0.615 Calibration of TNT Thermometers. Thermometer
12
used for detg “setting points” (solidification
For artillery weapons, the caliber is ex- points) of TNT by method prescribed by US Govt
pressed in the US & GtBrit in inches(and (See Specification JAN- T- 248) are calibrated
sometimes in millimeters), while in other for total immersion at the USBurStds. As the
countries in millimeters or centimeters. The Govt method of detg setting point is tedious and
word Caliber(or the abbr Cal) precedes the time consuming it is seldom used in plant
number, such as Cal 3.inch Field Gun, When the contrcd labs, except when lab results do no
word ‘‘ calibers” follows the number, such as in check with those obtd by Govt Inspectors. Just
the definition: “Gun,16-inch, 50 calibers”, it as precise and much quicker are the t ‘evaporating
means the length of the barrel is equal to 50 times dish” and “custard cup” methods, both of
the caliber(in this case 16”) which gives which employ thermometers calibrated to partial
50 x 16= 800 inches immersion when using such thermometers, it is
Calibers of current US artillery weapons essential that the lab temp stays within about
are listed in Vol l,p A386- R. Calibers of WWII 10°
German weapons are listed in Ref 4 Following is the procedure for calibration of
Refs: I) Anon, ‘ ‘Ammunition Inspection Guide”, thermometers intended to be used as “standards”
TM 9-1904(1944), 7 2)Ohart( 1946), 10 & 64-5 for plant control detns of sp’s of TNT’s: a)
3) G. M. Barnes, “Weapons of World War II”, Obtain a 50-lb box of good grade TNT b)Spread
Van Nostrand, NY( 1947) 4)PATR 251 O(PB No the contents on a very large piece of strong paper
161270 )(1958),PP Ger 227-59 5)Glossary of Ord and mix thoroughly with a large spatula and also
( 1959), 130 (See also Refs in Vol l,pp A387- L by lifting and lowering alternately the four
to A391- L) corners of the paper c) Bottle and keep in 1 or 21
wide mouth bottles, corked and sealed with
Calibration of Chemical Glassware at Plants paraffin. Keep away from light
Manufacturing Explosives and Related Items. d) Place in a large casserole
Inasmuch as practically none of the commercial about lkg of the TNT sample
volumetric glassware (such as flasks, burettes, and heat it in a steam oven.
pipettes, picnometers, nitrometer measuring After melting, heat the material
tubes, etc) is precisely calibrated by the man- ca 10 reins to dry it e)Arrange
ufacturer, it is advisable to recalibrate it in the an apparatus as represented in
laboratory where glassware is to be used. It is Fig. The cylinder shoul. be of
important to remember that none of the volumetric Pyrex, 2-zIX in diam and ca
glassware should ever be heated to high temps 20” long f)Heat the cylinder by
(above ca 500). This is because glass, expanded placing it in the oven g)Fill
by heating, does not resume its original form for the cyIinder to the top with
some time after heating molten TNT and insulate the
A complete description of methods used apparatus by placing it in
during WWII at the Keystone %dnance Works, sawdust, cotton, etc h)
Meadville,Pa was given in Ref Measure the ternp of TNT with
Re/: G. D. Cliff & B.T. Fedoroff, ‘CA Manual of an ordinary thermometer and if
Explosives Laboratories”, Lefax,Philadelphia, it is betw 82-83°, insert a
Vol 3, Chapter 2( 1944),pp 19,21,23,24 & 28 stopper fitted with a stirring
loop and a BurStds thermometer,
Calibration of Hydrometers. A simple, rapid with .02 divisions and calibrated
method is described in R.ef to total immersion i)Arrange the thermometer so
R e/: Cliff& Fedoroff, Vol 3, Chapter 2(1944),p that the top part of the stopper is on the level with
35 the 80.20° mark j )Stir constantly by moving the rod
up and down k)Watch the thermometer and as soon
Calibration of Laboratory Thermometers. A as the temp, after falling steadily, starts to
 C7

rise, stop stirring I)Note the temperature every heating and stirring the Iiq TNT becomes clear
15 seconds (by using special reading glass) until e)Heat one or.several custard cups to ca 85° and
the maximum is reached and record this temp as place them on wooden stands f)By means of a pair
sp. Add or subtract the bore corrections as of tongs, remove the beaker from the steam bath,
shown on the BurStds Certificate attached to the wipe adhering water from the outside (especially
calibrated thermometer. As the cylinder was around the edges) and pour the TNT into the
filled to the top, the thermometer was immersed in custard cup g)Insert a stirring rod about 6“ long,
TNT to ca 79.7°, leaving 0.5° of scale under the stir for few seconds and then leave without stir-
stopper. We may assume, without introducing an ring until a very light crust starts to form on the
error of not more than 0,01 0, that the thermometer surface of TNT. This will mean that temp of the
was totally immersed molten mass has dropped to about 2-3° above sp
Suppose now that correction of BurStds Note: If thermometer is introduced in the mass
thermometer is +.05° and its reading for sp of TNT while temp is much higher than sp of TNT, serious
is 80.20°. This means that sp of TNT is errors may be introduced, because the expanded
80.20+.05= 80.25°. Save the rest of this TNT glass does not immediately resume its original
(few pounds) and use in fiture as the standard volume. Also broken mercury columns are more
TNT likely to occur
The BurStds thermometer and other h)Break the crust by means of the stir-
thermometers calibrated for total immersion should ring rod and insert two TNT thermometers as
be used only for detn of sp of TNT by the shown in Fig i)Stir the, mass with the glass rod
Specification Method, whiIe for routine tests the (and not with the thermometer to avoid breaking
thermometers calibrated to partial immersion of Hg bulb). Lift the thermometers and carefully
should be used. For calibration of such remove the crust of TNT using a spatula or
thermometers proceed as follows: a)Make a mark knife. Reinsert the thermometers and lean them
ca 5cm from the bottom of the bulb and at least against the notch of the stand. Be sure that TNT
lcm above the upper (small) mercury bulb on covers the immersion mark of thermometers (See
each special thermometer graduated in 0.1 or opn a) j )Stir occasionally watching the thermome-
0.05° b) Tie thermometers together in pairs (with ters with’ the naked eye k) The temp will drop
a strip of rubber tubing) and be ready for until it reaches ca 1° above the sp. After this
calibration by custard cup method c)Wash and dry the temp will start to rise due to the latent heat
a Pyrex custard cup ca 2.5” in diam and ca 2.5” of crystn. At this point the mass turns fudgy and
deep. In order to hold the cup and thermometers becomes slightly lighter in color I)Stop stirring
in place, use a wooden stand as shown in Fig and slightly raise the thermometers so that the
bottoms of lower bulbs are ca lmm above the
crust on the bottom of the cup, while the upper
(small) bulbs remain completely covered by TNT
m)WhiIe holding thermometers steady in this
position, observe closely the temp (which should
rise slowly at this point of detn) using a special
magnifying reader. As soon as the temp stops
rising and remains stationary for some time, take
a reading and record it as the sp
Note: If a reading lens is used, hold it flush
against the stem of the thermometer and read the
temp to 0.01°
Calculation: Let us suppose the thermometer No
d)Fill one or several 180-ml electrolytic beakers
1 shows 80.31° while No 2 shows 80.21°, As the
to the top with “standard TNT” and melt the TNT
true sp of “standard TNT”, as detd by the
on a steam bath. Add more TNT and continue
BurStds thermometer was 80.25°, it mems that
heating until the temp is betn 85 & 87° the total correction for No 1 will be minus .060,
Note: If it is suspected that TNT is slightly while for No 2, plus .04°
moist, continue heating and stirring for addnl Cleaning of Glassware Used in Calibration of TNT
10 reins. If TNT is very moist, add 1-2 table- Thermometers. As soon as the reading is taken,
spoonsfuI of anhydrous Ca chloride and continue remove the thermometers from the cup and hold
 I

C8

one of them with the left hand close to the 5°, and separated in centrifuges from other salts
adhering mass of TNT, with index finger which have remained in soln e) Before sacking,
underneath the mass. Using me right hand and a the product thus obtained is melted and sprayed
piece of paper, push the TNT off the bulb. If TNT to form little globules in order to prevent caking
became too hard, remove it by means of a during shipment
spatula of knife. Another method is to place the More detailed info on production of Na
bulb of thermometer for ca 10 reins in a jar nitrate may be found in Ref 1 & 2
contg nitration grade toluene. The same toluene Re/: l) Wm.H.Rinkenbach, ArOrd 11, 11 O–14(I93O)
may be used for many cleanings and then 2) H. L. Reichart & H. W. Schulz, ChernMetEngrg 46,
returned to the plant for use in the nitration to 464-6( 1939) 3)Kirk & Othmer 12(1954), 605
TNT. This method is safe and recommended
especially if the crest is allowed to cool so Caliver or Arquebus of Caliber. See under
that it becomes very hard. A hot thermometer Arquebus in Vol l,p A488- L and under BULLETS,
should never be inverted or placed horizontally, Historical
in order to avoid splitting of the mercury column.
For removing TNT from custard cups allow the Callenburg’s Dynamite, patented in 1899,
contents to cool to RT and then tap the cups consisted of NG 30, collodion cotton 1, K nitrate
lightly in an inverted position against a wooden 40, MgS04.7H20 24, turpentine 4 & Na carbonate
object (such as a table), but not against metal or 1$% It was practically nonhygroscopic and only
stone. The TNT will be released as a solid slightly sensitive to shock or heat
piece Re/.’ Daniel(1902), 105
R ef: Clift & Fedoroff, Vol 3, Chapter 5(1944),
pp 4-6 Cal.Nitro. A trade name for AN compn manufd by
Semmett Solvay Co of Hopewell,Virginia for use
Calibration of Weights and Analytical Balances. as a fertilizer. It is less reactive with paper and
A simple, rapid method is described in: sawdust than FGAN(see Vol l,p A364), does not
R ef: Clift & Fedoroff, Vol 3, Chapter 2(1944), yield significant amts of expl gases (when
pp 36-8 decomposed at relatively low temps) and the
bagged material is slightly less fire hazardous
Caliche or Nitre-Bed. A term used in Chile for a than bagged FGAN(see also Uraform- AN)
layer of-gravel or rocks contg Na nitrate (Chile Re/: K. G. Ottoson, PATR 1682(1948)
saltpeter) together with Na sulfate (salt cake), Na
chloride (table salt) & small amts of other salts. Calomel. See Mercurous Chloride under Chlorides
Caliche varies in depth from 2 to 20ft and is
covered by 1 to 12ft of sand overburden. The Calorie or Calory. In metric system it is the heat
deposits are found in a desert in Atacama of required to raise the temp of lg of water from to
province Tarapaca (Northern Chile) extending (such as 15,18 or 20°) to (t+ l)O. This is called
400 miles north and south with a width of 5 to “small” or “gram- calorie” (abbr cal). There is
40 miles. Deposits of Na nitrate, on a smaller also “large” or “kilogram- calorie” (abr Cal or
scale have been found in Argentina, Bolivia, kcal) which is equal to 1000cals. In English
California and Peru (Ref 1, 2 & 3) system, the so- called BTU or btu (British
The modern process for extraction of Na Thermal Unit), is the heat required to raise the
nitrate from caliche (as well as from lower grade temp of llb of w from 39.1 to 40. 1°F. One BTU
ore called costra) was developed by Guggenheim is equal to 0.252kcal
Bros of New York. Essentially it consists of the Re/s: I)H.S.Taylor & S.*Glasstone, t ‘A Treatise
following operations: a)Th e sandy overburden is on Physical Chemistry”, Van Nostrand, NY( 1942),
removed by means of large drag lines b) The 439–40 2)Hackh’s (1944), 160 3)Handbooks of
caliche is broken by blasting, loaded by steam Lange or of Chemical Rubber Co
shovels, and transported to the leaching plant by
means of a temporary electric RR) c)The caliche Calorific Constant of Explosives or Propellants.
is crushed into small pieces and then leached in It is defined by Taylor et al, as the heat evolved
I arge open vats counter-currently with water at or absorbed on decompn of O.Olg of a substance at
ca 40° d)The nitrate is recovered by crystn at const vol and at 33° (water liquid). It can be
 C9

calcd from the formula: %Nin NC 13.24 13.10 12.73 12.16

h=qH /( 100 x gram- molecular wt), where h is Calorif ic 1063 1054 982 902
calorific constant and qH -molecular calorific Value s(cal/g)
value (see under Calorific Value of Note: Values for NC’s are corrected for methane
Nitrocelluloses and Propellants) formation. If no correction for methane is made and
Re/: J. Taylor et al, JPhCoIIChem 51, 584(1947), the temp is that of experiment, the corresponding
& CA 41, 3967(1947) values would be: 106O, 1051, 980.5 & 900.5 cal/g
Calorific values of proplnts can also be
Calorific Values of Explosives. Calorific value detd experimentally. They may be calcd aIso by
is defined by Weissberger (Ref 3) as t ‘the heat using the following equation:
evolved when the substance is exploded in the Q=(aQA+bQB+~ . ..mQM)/( a+b+~ . ..m). where
absence of oxygen except for what it contains a.parts of component A & QA its calorific value;
itself”. This quantity is practically the same as b=parts of component B & QB its calorific value,
the heat evolved when the substance is exploded etc. The components may be either expl or
under normal operating conditions (such as in nonexpl
bore holes or in shells). Experimental techniques If the compn of a proplnt is CPHqNyOs and
differ somewhat from those employed in ordinary if F its heat of formation, then we might write
combustion calorimetry. The bombs employed in CPH Nr0s=pC02+(s- 2p)H20+(q/2- s+2p)H2
calorific value techniques are smaller in capacity +r/2fi,-40987p+67509s- F(Ref l,P 585)
and possess very thick walls to withstand high The molecular calorific value of the above
pressures. For example the bomb described in proplnt, at const vol, at 33° and with w liq would
Ref 2 is of 124cc capacity. It was developed at be;
Woolwich Arsenal and modified by Taylor et al, qH= -40657P+ 67343 s- F,
The Parr Instrument Co of MolineyIllinois also where p=number of carbon atoms in proplnt,
manufactures similar thick-walled bombs s=number of oxygen atoms and F=molecular heat
Calorific value of an explosive is closely of formation of proplnt
related to the value called heat o/ explosion or Note: The value qH may be either positive or
beat of detonation, and if an explosive contains negative accdg to whether heat is evolved or
sufficient oxygen for complete combustion to absorbed on the decomprt and reaction of the
C02 & H20_, the calorific value may be considered compd
as identical with the beat of combustion If the molecular calorific value is known,
For example, for NG which has oxygen the corresponding calorific constant can be.calcd
balance to C02 & H20 equal to +3.5%, the above using the equation given under Calorific Constant
values are equal to 1615cal/g(or 341.1 kcal/mole) (Ref 2,pp 580- 6)
at const vol, at 20° & with water liquid (Ref 1) Calorimetric Value is defined by Corner(Ref 3)
Re/s: I)J.Taylor et al, JPhCollChem 51, 580-92 as the value which is obtained by measuring the
( 1947) & CA 41, 3967(1947) 2)J.TaYIOr & heat evolved when a propellant is burned in a bomb
C. R. L. Hall, Jphcollchem 51, 593-8(1947) 3) calorimeter contg an insert atmosphere. Tb e
A. Weissberger,Edit, “Physical Methods of temps are near 300 o Kc This value can also be
Organic Chemistry”, Interscience, NY, VOI 1, calcd as shown in Ref 3,pp 127-8
Part l,p 591: J. M. Sturtevant, “Calorific Values Calorimetric Potential, Apparant (Potentiel
of Explosives” calorim6trique, apparent in Fr). Tavernier (Ref
4,P 234) defines it as the quantity Of heat
Calorific Values, Calorimetric Values and evolved on the decompn of a proplnt, provided it
Calorimetric Potentials of Nitrocelluloses and does not do any exterior work (which means
Propellants. Taylor et al (Ref 2,p 580), define the under const vol) and if the gases evolved in
calorific value as the heat evolved (in calories reaction are cooled (which means that the water
per gram) when a substance is exploded in a is liquid). This value is, accdg to Tavernier~
special calorimetric bomb capable of withstanding identical with the English value called
high pressure “Calorific Value”. A similar value was called by
The following experimental calorific values DeP auw (Ref 1) “die Characteristic einer
for NC’s of various N contents, at const vol and Substanz”
corrected to 0° are reported by Taylor & HalI The above value may be called “potentiel
(Ref 2a,pp 606 & 609, tables 4 & 10):
 i

c 10

calorim6trique apparent normal” to distinguish it calorimetry and the tests involved are known as
from “coefficient calorim<trique fictif” calorimetric determinations. These tests
designated by Tavernier as Qa(Ref 4,p 251)* Qa include: determination of heats of combustion,
is the heat liberated at const vol with w liq in formation, vaporization, fusion, solidification,
cal/g. It is applicable to an org compd sublimation, atomization, isomerization,
cxHyXl O z with less oxygen than is required solution, dilution, mixing, absorption, chemical
for complete formation of C02& H20, but combination and of chemical decomposition. The
greater than that required to oxidize all calorimeter may also be used for detn of
carbon to CO. Equations are derived specific heats and melting points (Refs 1-5,15,
and discussed graphically to show that 20,22,24,25,26,27 & 28)
Qa=67409z- 40698x- Qf, where Qf is the heat of The most important of these tests is the
formation of the substance and determination of heats of combustion (See below)
12x + y + 14u + 162=1 from the formula The importance of calorimetry in the
CxH#uOz. The val Ues Qa are shown to be study of chemical reactions was recognized as
additive for a mixt in terms of the percentages of earlY-as ca 1.790, when Lavoisier & Laplace
each, providing the O balance is within the same invented the “ice calorimeter” (Ref 28)(See also
range .Ref 3,p 21)
In Ref 6, Tavernier gives simplified Further developments in calorimetry
equations for the explosion temperature at const include the invention of the “twin-calorimeter”
vol, the calorimetric potential, the av sp heat at
by Joule (1845) and its modification by Pfaundler
const VOI, the force and the coeff of isentropic ( 1869)(Ref 25,P 543); “phase-change calorimer”
expansion for proplnts, CXH NUOZ, where (isothermal) of Bunsen(Ref 15,p 796 & Ref 25,p
12x + y + 14u + 16z=1 and z x + y/2- z>O and 547); “labirinth flow calorimeter” (Ref 25,p 549);
Z—x>o “adiabatic calorimeter” (nonisothermal), first
Muraour et al(Ref 5,p 273) define “potentiel used by Richards in 1905 (Ref 15,p 797) and
apparent” as the heat of explosion or deflagration, modified by Yost, Osborne & others (Ref 25 ~p
as detd in a calorimetric bomb at const vol either, 550)( See also Ref 3,P l16)(parr adiabatic
in vacuum or in inert atmosphere. This differs calorimeter is described in Refs 16 & 29);
from “chaleur de combustion” (heat of ‘ ‘constant- .temperatute= environment calorimeter”,
combustion) which is detd in the bomb in the first used by Nernst in 1907, was modified by
presence of an excess of compressed oxygen. In Giauque in 1923(Ref 15,p 797)
the opinion of Muraour et al, it is much simpler, Qher calorirmters include: c ‘ heat-leak
less time consuming, and more precise to det and calorimeters”, such as of Thomas & Parks
use the values of heat of combustion in lieu of
( Ref 25,P 545), ‘<automatic calorimeters” such
calorimetric values as of Andrews, Berl & Stun (Ref 25,p 551);
Lamouroux (Ref 7) discusses conditions for C%acwn- walled calorimeter” (Ref 3,P 153);
detn of “potential calorim~trique apparent” of “aneriod (unstirred) calorimeters” (Ref 3,pp
smokeless proplnt= 23,160 -7), f ‘rotating bomb calorimeters”, such
Refs: l) P.dePauw, SS 32, 11(1937) 2)J ,Taylor et as of Popov, Shirokikh and of Hubbard (Ref
al, JPhCollChem 51, 580- 92(1947) & CA 41,
25,P 594); liquid-phase calorimeter” of
3967(1947) 2a)J.Taylor & C. R. L. Hall, Kistiakowsky (Ref 25,p 636), “gas calorimeter
JPhCollChem 51, 593-8 & 606- 11(1947); CA 41, of Cutler- Hammer (Ref 18a), ‘ ‘calorimeter for
4030(1947) 3)Corner, Ballistics(1950) 127-9 gaseous heat capacities of Waddington (Ref
4)P.Tavernier, MP 35, 233- 58(1953) & CA 49,
15,p 802), “flow calorimeter of Junkers” (Ref
12832- 3(1955) 5)H.Muaour, W 35, 273-86
15,P 805)$’ flow calorimeter of Osborne et al”
(1955) 6)P.Tavernier, MP 37, 225- 68(1955)&
(Ref 25,P 565), “flow calorimeter of Pitzer”
CA 51, 1609(1957) 7)M.Lamouroux, Mp @,
(Ref 25,p 566), “flow calorimeter of
241-5(1958)
Bennewitz & Schulze (Ref 25,p 567) and
‘ ‘flame calorimeter of Rossini” (Ref 25,pp
Calorimeter, Calorimetry & Calorimetric
600-2). An apparatus for detn of heats of
Determinations. Calorimeter is any apparatus
vaporization is described in Ref 25 ,p 615 and
used for measuring the quantity of heat, absorbed
an ‘Adsorption calorimeter” in Ref 25,p 618
or evolved, during any chemical or physical
Microcalorimeters are described in Ref 13
process. The art of measuring this heat is calIed

—- —. —.-
 cl]

and a semi- microcalorimeter in Addnl Ref C are in Ref 16

Some original papers on calorimeters are The Parr Co also manuf “peroxide bombs”.
listed under ‘ CAddnl Refs on Calorimetry”, which These bombs are small pressure vessels in which
follows Refs samples are subjected to the intense oxidizing
For detn of beats of combustion of gaseous action of Na peroxide at a temp high enough to
materials or of volatile liquids, special completly burn almost all C compds. Powdered K
calorimeters are used. in the “gas calorimeter”, perchlorate and ‘other reagents can be used
such as Cutler- Hammer described in Ref 18a, a together with peroxide to assist and accelerate
predetermined vol of gas is burned and the evolved ignition and to carry the reaction to completion
heat is transferred to a material of known sp heat (See Parr Specification No 2000)
(such as air or water) and of known temp. In a In France, they have been using calorimeters
C“flow calorimeter”, such as of Junkers, described which are modifications of original B erthelot
in Ref 15,p 805, the gases evolved, on burning, aPParatus. One such, “Landrieu- Malsallez, is
heat the w flowing at const rate and the heat is installed in College de France (Refs 6 & 8). This
detd from the wt of w and the temp rise. In a calorimeter and the bomb of “Burlot- MalsaHez”
C‘flame calorimeter”, such as of Rossini, described were manufd before WWII by the Usines Chimiques
in Ref 25,pp 600-2, the gaseous or highly volatile Rh6ne- Poulenc. Another Fr calorimeter is that of
materials are conducted thru a silcon tube into a the Commission des Substances Explosives. It is
reaction chamber where they burn in an excess specially designed for testing expls (Ref 6).
of oxygen, The reaction vessel is immersed in a Stettbacher (Ref 7,p 84) mentions that one of the
calorimeter contg w, and further procedure is the bombs designed by Bichel was using 100g sample
same as for detn of heats of combustion of solid For detns of heats of explosion, bombs
materials (See also Ref 22) similar to above but with thicker walls and of
For detn of combustion of solid and non smaller capacities are used. Several bombs
- volatile liquid materials, the most convenient designed for this purpose are used at Picatinny
method is to use a f ‘closed bomb calorimeter”. Arsenal. All of them are cylindrical in shape and
The first closed bomb calorimeter using oxygen were manufd by the Parr Co. A similar small
under pressure was developed in 1881 by capacity bomb but made of Vibrac steel was
Berthelot (Refs 1,15 & 16). It was improved by developed in England by Research Dept, Woolwich
Mahler in 1892 and by Atwater in 1899. These (now Armament Research Dept). It is described
bombs were made of steel with linings of Pt, Au, in Addnl Ref n,pp 593-8. Stettbacher (Ref 7 ,pp
Ni or vitreous enamel. This construction was 83- 4) describes the bomb of J. Peters, which was
costly, and complete protection from corrosion was of 40ml capacity, and used 10g samples. It could
not always obtained by lining. These difficulties withstand very high pressures (See also Calorific
were overcome in 1912 when Prof S. W.Parr Values)
developed a bomb made of an alloy “Ilium”, R efs: l)M.Berthelot, “Thermochimie”, Gauthier
comparatively inert to acids formed as result of - Villars, Paris (1897) 2)Marshall 2(1917), 440
combustion. This type of bomb is now manufd by -4 3)W.P.White, “Modern Calorimeter”,
the Parr Instrument Co, Moline, Illinois and the ChemCatalogCo, NY( 1928)(ACS Monograph NO 42)
alloy used for its body consists of (approx):Ni 29) 4) W. Ostwald, R. Luther & C. Drucker,g CPhysikalische
Cr 20, Mo 2, Cu 3, Si 1 & Fe 45%. The alloy is Mes sungen”, AkadVerlagsgesell schaft, Leipzig
fundamentally similar to the original “Ilium”. (1931) 5)C.E.Munroe & J. E. Tiffany, “Physical
The trade mark of the present type of alloy is Testing of Explosives”, Bur Mines Bull 346,
“Type 20 alloy”. Parr combustion bombs are USGPO, Washington, DC(1931)$ 99-104 6)Vennin,
described in Refs 16 & 29, and on pp 16-17 of Burlot & L6corch6(1932), 63 7)Stettbacher(1933),
Ref 16 are given cross section views of “plain 78-85 8) Pepin Lehalleur (1935), 44 9)
jacket calorimeter, series 1300” (Fig 8) and of R .R.Wenner, “Thermochemical Calculations”,
“adiabative calorimeter, series 1200” (Fig 9) McGraw- Hill, NY( 1941) 10)Meyer(1943), 371-3
Parr calorimetric bombs and calorimeters are 1 l)Vivas, Feigenspan & Ladreda 4(1944), 82-4 &
very much in use in the US. These bombs are 95-104 12) B. F. Dodge, ‘{Chemical Engineering
cylindrical in shape and are provided with covers Thermodynamics”, McGraw- Hill(1944) 13)
which can be securely closed against leakage. W. Swietoslawski, “Microcalorimetry”, Reinhold,
Detailed descriptions of experimental procedures NY( 1946) 14)S.Glasstone, “Textbook of Physical
using Parr oxygen bombs and Parr calorimeters Chemistry”, VanNostrand NY(1947), 207-11 15)
 c 12

Kirk & Othmer 2(1948), 793-808 (Calorimetry)(69 on heats of combustion )(Five papers) l) J. G. Aston
refs) and 13(1954), 941-52 (Thermochemistry )(4 et al, IEC, Anal Ed 19, 218 -21( 1947)( Melting
refs) 16)Parr Manual No 120, Parr Instrument Co, point calorimeter for purity detns) m) G. Waddington
Moline, 111(1948) 17) F. D. Rossini, “chemical et al, JACS 69, 22 -3O(1947)(F1OW calorimeter for
Thermodynamics” ~ Wiley(1950) 18) R. L, Weber, gaseous heat capacities and heats of vaporization>
“Heat and Temperature Measurement”, Prentice n) J. Taylor & C. R. L. Hall, JphCollChem 51, 593-8
-. Hall, NY(1950) 18a)Perry(1950), 1301-2 19) ( 1947)(Description of a Brit bomb for detn of heats
S. Valentiner, “Physikalische Grundlagen der of expln) o) L. M6dard & M. Thomas, MP 34, 421-42
Messtechnik in der Warmewirtschaft”, Verlag fiir ( 1952)(Detn of heats of combustion of 12
angew Wissenschaft, Wiesbaden(1953) 20) substances used as components of expls &
J .Reilly & N. W.Ray, “Physico- Chemical proplnts) p)H.Muraour, MP 35, 272- 86( 1953)(Heat
Methods”, VanNostrand, NY, vol 1 (1954), 495 of combustion values of proplnts used as means of
- 527( Thermal measurements) 21 )W.Moore, control in the manuf of proplnts) q)W.W.Hubbard
‘ ‘Physical Chemistry”, Prentice- Hall, NY( 1955) et al, JPhChem.58, 142-52 (1954)(A rotating
39-45 22) F. D. Rossini, Edit, “Experimental combustion bomb for precision calorimetry) r)
Thermochemistry, Interscience, NY(1956) 23) S. B. Pandaya & P. M. Verma, JSciIndResearch
W-Roth & F, Becker, ‘ CKalorimetrische Methoden (India) 13B, 642-56(1954)& CA 49, 10675-6
fiir Bestimmung chemischer Reaktionswtirmen”, ( 1955 )( Practical bomb calorimetry) s)R. A.Mott et
Vieweg, Braunschweig (1956) 24)Funk & al, Fuel 33, 448-61 &462 -79(1954); 34, 283-316
Wagnalls, ‘ ‘New Standard Dictionary”, NY( 1958), (1955) and 35, 261- 79(1956); CA 48, 14152-3
379-83 25)A.Weissberger, Edit, ‘ ‘Physical (1954); 49, 12050- 1(1955) and 50, 11726(1956)
Methods of Organic Chemistry”, Interscience, NY, (Bomb calorimetry) t) G. Seitz, Explosivst 1955,
VOI l,part 1(1959), 523-654: J .M.Sturtevant, 173-8 & 201- 6( Investigation of combustion of
‘ ‘Calorimetry’ ~ 26)R.S.Jessup, “Precise proplnts in a closed bomb) u) P. Tavernier &
Measurements of Heats of Combustion with a Bomb M. Lamouroux, Mp 37, 197- 205(1955 )( Ca10rimetric
Calorimeter”, USNBS Monograph No 7, Washington, investigation of 12 organic substances in view of
DC(1960) 27)S.Glasstone & D. Lewis ‘ ‘Elements their utilization in proplnts) v) L. M6dard &
of Physical Chemistry”, VanNostrand, NY(1960) M. Thomas, MP 38, 45-63 (1956 )(Detn of heats of
28)Merriam- Websters (1961), 320 29)parr combustion of 13expl substances) w) P. Tavernier
Specifications No 1100-1105 (Describes various & M. Lamourou~ MP 38, 65–88(1956)(Detn of heats .
bombs and calorimeter and gives literature on Parr of formation of 26 organic substances) x) P. Miaudj
apparatuses; may be obtained on request from Parr MP 38, 181- 8(1956) (An improved manometric bomb
Instrument Co, Moline, Illinois) for investigation of combustion of proplnts) y)
Addnl Refs on Calorimetry: a)M.prettre, ~P 24, C. A. Neugebauer, “Standard Heats of Formation by
223- 33(1930 )(Detn of heats of combustion of NC’s Rotating and Stationary Bomb Calorimetry”,
and of cellulose) b) F. D. Rossini, JRNBS 6, 1-49 Thesis, Univ of Wisconsin ( 1957), Univ Micro-
(1931); 8, 119-39 & 12, 735- 50(1934)( Various films, AnnArbor,Mich, Publication NO 21224 Z)
calorimetric measurements) c)D.R.StuH, JACS 59, D. R. Stun, Anal ChimActa 17, 133( 157)( Automatic
2726( 1937) (Semi- micro calorimeter) d)F. T, Gucker calorimeter) aa)C.Napoly et al, Mp 41, 155-69
et al, JACS 61, 459( 1939)( Differential adiabatic (Contribution to the study of operating conditions
microcalorimeter) e)L. G, Carpenter & A. R. Bryant, for detn of calorimetric potential in calorimetric
JSciInst 16, 183- 92(1939) &CA 33, 5707(1939) bombs) bb)S.S.Wise, ‘ ‘The Heats of Formation of
(High temp vacuum calorimeter of the copper Some Inorganic Compounds by Fluorine Bomb
- block type) f)E.Burlot, MP 29, 226-63( 1939) Calorimetry”, Argonne National Laboratory ANL
(Discussion on calorimetry of expls) g)M.Badochq -6472, Jan 1962, Contract W- 31-109- eng- 38
MP 29, 280- 2(1939 )(Detn of heats of combustion
of various nitrocompds) h)C. B. Miles & H. Hunt, Calorite. A French incendiary pyrotechnic device
JPhCollChem 45, 1346 -59( 1941 )(Detn of heats of used during WWI. It was prepd in ~ form of a block
combustion) i) E. R. Prosen & F. D. Rossini, JRNBS by binding a mixt of powdered A1 & Fe oxide with
27, 289-3 10( 194 1) (Calorimetric procedure for liq Na silicate. The dried material was ignited by
detn of heats of isomerization of hexanes) j) means of a fuse combined with a primer consisting
R. B.Scott et al, JRNBS 35, 39 -57( 1945)(High of powdered Mg & Ba peroxide
- precision adiabatic vacuum calorimeter) k) R ef: Pepin Lehalleur(1935), 475
J .Coops et al, Rec 66, 113 -76( 1947 )(Researches

1 .—_—.———,_.._ —-.— .—.

 c 13

Cambrites. Britmining explsmanufdby the (frames per second). In 1909, C. Cranz designed an
Nobel’s Explosives Co, Ltd, Ardeer, Scotland and apparatus called “Ballistische Kinematograph”,
placedin 1901 on the “Permi~ted List”. The which was capable of taking up to 5000fps(Ref l,p
original Cambrite No 1, was prepd by mixing 351). An improved app taking up to loOOOOfps was
Nobel’s Carbonite 92 & Amm oxalate 8%(Ref 1). devised in 1912 by C. Cranz & B. Glatzel(Ref l,p
This corresponded to compn given in Ref”2 as: NG 356)
23, K nitrate 27, Ba nitrate 3.5, woodmerd 38, Amm The first successful moving picture camera
oxalate 8 & Ca carbonate 0.57.. The compn of and projecting apparatus were invented in 1895 by
Cambrite No 2, was: NG 22-4, K nitrate 26-9, Ba W. Lathan(US) and simultaneously bj
nitrate 3-4.5, woodmeal 32-5, KC1 7-9 & Ca L. & A, Lumi?re(France). These and other early
carbonate 1% (Refs 3 & 4). The compn No 2 is moving- picture cameras were hand- operated, using
called in Ref 4 ‘ ‘smokeless powder” intermittent motion of the film and shutter. When
f?e~: l)Daniel(1902) 105 2)Marshall 1(1917), 376 they were modified to be electrically operated,
3)Thorpe 4(1940), 553-4 4)CondChemDict( 1942), their fastest picture taking rate became 128fps. As
288 (not found in later editions) these cameras were much too slow for ballistic
study, they were mechanically modified to obtain
CAMERAS, HIGH- SPEED PHOTOGRAPHIC(Used framing rates up to 1000 Ofps(Ref 18,pp 31-2)( See
in Study of Rapid Events). In ballistic and also Ref 21,v 17,p 811)
aerodynamic investigations as well as in the
study of explosive parameters, events are of such Cameras, Modern. At present there are methods by
short duration that it is impossible to observe them which the rate of 1000Ofps can be exceeded and
visually. If such events are recorded this is known as “ultra high- speed photography”.
photographically, detailed analyses and For example, B. O’Brian of the Univ of Rochester,
measurements can be made. Rapid events, such NY designed a camera with the rate of 15000fps
as detonation, explosion, deflagration, blast and in England research was conducted to design
effect, shock wave travel, flight of a projectile, a camera of 50000 fps(Ref 18,p 101)
etc are of such short duration, that special cameras In the methods where a series of photo-
have been designed and built to conduct these graphs are taken in rapid succession, there are
studies two fundamental physical parameters, which are of
High- speed photography (Momentphotogra- importance: the “picture repetition rate’’(R) and
phie or ~urzzeitphotographie in Ger and the “time of exposure’’(T) of each individual
Photographic ultra-rapide in Fr) may be frame. R is expressed as “frames per second”
subdivided into “still” and “motion picture” ( fps) and T is given in microseconds. In different
Accdg to EncyclBritannica (Ref 2 l,v 17,P cameras, R may have values ranging from 24 to well
811), high- speed photography may be divided into: over 106 fps with T varying from ca 0.1 to 2000
a)Single-instantaneous photography (which microsecs. Closely associated with the value of
includes shadow or silhouette method, schlieren R, is the ‘ ‘maximum time” (T) for which an event
method, Kerr-cell method, reflected and can be studied due to practical limitation of the
stroboscopic light method, spark method & method
electronic flash method) and b)Motion- picture Following is a brief description of devices
photography (which includes Bell Laboratories and techniques which have been used to study
and other recently developed cameras) rapid events:
High- speed photographs may be taken with A) Cathode-Ray Oscillograpb Photography. It is a
oridnaty reflected light, with monochromatic light, graphic method of obtaining permanent records in
with infrared light, with ultraviolet light or with the analysis of amplitudes and frequencies of
X-rays eiec & mechanical phenomena(Ref 3, 13a, 17b,
Historical. The first attempt to photograph a rapid 23c & 25c). The US ordn Lab has developed and
event was made ca 1850 by H. F. Talbot of Engiard built a high- speed oscillograph capable of
He used a still camera and as a source of light the recording six traces simultaneously on a 35mm
sparks generated by the discharge of a Leyden jar film. With the help of this instrument it was
thtu an air gap. Talbot’s technique was applied possible to investigate the function of guns,
in 1884-5 by E .Mach & p.salcher to ballistic recording the breaking time of the primer bridge
studies. Later L.Bull of Paris used an oscillation wire, the instant of appearance of flame from the
spark discharge to obtain a framing rate of 2000fps primer port holes, the beginning of recoil of the
 c 14

gun, and pressure-time records at three positions 5 1). These cameras may be called “elecwic flash
along the shell case(Ref 15a) cameras”. The flash produced by an “exploding
B)Cine Camera. Same as Motion Picture Camera wire” is also use&as a light source (Ref 28). An
C) Continous Film Movement Camera. It is a electronic flash is produced by various electronic
device permitting one to take a rapid succession tubes and the cameras may be called “electronic
of pictures of an event on a continuously moving flash cameras” (Ref 29,Pp 161-79; Ref 31,pp
film. With this camera it is possible to achieve 443-68 and Addnl Ref q)(See also Intermittent
repetition rate of 16000fps(Ref 32)( See also Ref Light Source Camera and Spark Photography)
18,p 14 and compare with “Intermittent Film H) Flash Radiography. See X- Ray High–Speed
Movement Camera”) Photography
D)Drum Camera. In this camera a strip of film is I) Framing Camera, High- S/reed. A camera
wrapped either on the outside or on the inside of a producing a series Of “distinct” pictures (frames)
narrow hollow drum. The device, in which the drum at “framing rates’ ‘(R) above 100t)OOfps may be so
is rotating at very high speed past optical called. There are ‘tsingle- framing” and
components, is called a “rotating drum camera with t ‘multiple- framing” cameras. AEC-Bowen,
moving film” to distinguish it from a camera in B eckman-Whitley, Image-Converter, Image-Dissector
which the film is stationary on a fixed drum and and Multiple Kerr- Cell cameras are examples of
succession of images is formed on the film by framing cameras (Ref 25a,p 23 and Addnl Ref hh)
reflections from a rotating mirror. This latter type ]Xmage Converter Camera. It consists of an
is known as a { ‘rotating(or spinning) mirror electronic tube having a photocathode at one end
camera”. Some drum cameras combine a rotating and fluorescent screen at the other end with
drum with rotating mirrors (Ref 18,pp 14 & 80 associated tube components. The image is formed
- 104; Ref 25,pp 289 -336). Another type of drum on the photocathode. The electrons given off are
camera uses “rotating prism” (Ref 15a; Ref 25,pp relayed and focused onto a fluorescent screen by
351- 7; Ref 31,P 367) electronic means. The visible image can then be
Notes: l) Because of considerable mechanical photographed by conventional methods (Ref 25, p 116
difficulties for rotating the drums at very high Ref 25a,p 23 & Ref 32)
speeds, the principle of “frame division” has K)lmage Dissector Camera, also called “Image
been used to increase repetition rates of pictures. Splitting” or “Image Sampling” Camera. The
This subject is discussed in detail by Chesterman image dissection techniques consists of sampling
(Ref 18,pp 80-5 2)When photographic recording a large number of line or point images by means of
methods are used with the film wrapped either on slits (Ref 14a), grids (Ref 17b & Ref 25,pp
the outside or the inside of rotating drum, but no 96 -101), lenticular plates (Refs 23a & 25b)(and
“discrete” images are formed, the method is the like(Ref 32)
defined as c‘chronographic”. For more info on L)lnterferometer Camera. E.Mach and his son
this subject, see Ref 18,pp 85-9 L.Mach were the first to apply interferometer
E) Electric Flash Camera. See under Flash techniques to study of ballistic problems (Ref 1,
Photography p 275). The camera devised by them was improved
F) Electronic Flash Camera. See under Flash by Zehnder and became known as ‘ ‘Mach
Photography -Zehnder Interferometer” (Ref 2,p 173; Ref 18,p
G) Flash Photography. It is the method of 141 and Addnl Ref old). Bennett et al (Addnl Ref
photographing objects with the aid of illumination cc)gave the theory of interferometric analysis and
produced by a flash. The flash may be produced described the procedure used at BRL(Ballistic
by nonelectric, electric or electronic sources. A Research Laboratories), Aberdeen, Md for analysis
‘ nonelectric” flash may be produced by various of airflow around projs in flight. The app of
‘ ‘flash” powders, such as of Mg(Ref 8a); by Tolansky is described in Ref 31
detonation of a small expl chge, such as of M)lntermediate Rate Camera or Medium Repetion
Pentolite (Ref 18,pp 54–5); by explosively shocked Rate Camera. A camera with repetion rate (R) up
argon gas (Ref 32); or by other methods (Ref 31,pp to 1000OOfps, in which the time scale of the event
49-65). An “electric” flash may be produced by on projection of the film is multiplied by a factor
one of the numerous “photoflash bulbs” or by of approx 4000fps may be so called. Many of such
“flash discharge tubes” (gas- filled or cameras both for 35 or 16mm films have been
stroboscopic)(Ref 18,pp 48-5 I)(See also Ref 3,pp developed (Ref 18,pp 18 & 23; Ref 25,pp 337-60
3-1o; Ref 12a; Ref 14; Ref 18,P 148 and Ref 25~P and Ref 32)

—-. .—.—e ——.. -, — .——

!
 c 15

N)Intermittent Film Movement Camera. , A camera (Ref 18,p 78). Pugh et al (Ref 18a) described a
in which it is possible to record a rapid Kerr-cell camera for photographing metal jets
succession of images by arresting the film squirted ‘from lined conical cavities of shaped HE
movement at the instant when exposure is desired, chges, Previous attempts to photograph them by
may be so called. Shutter mechanisms alIow visual lighr were unsuccessful because the velocity
individual picture-exposure times to be varied over of such jets is extremely high, while their
a ratio ca 20:1 (Ref 18,p 13) luninocity is very low. As a source of fight Pugh
O)hermittent Light Source Camera. For some used an “exploding wire” (See also Ref 25,p 133;
research studies it is often necessary to have a Ref 29,pp100-2; Ref 31,pp 127-40 & 453-4)
considerable number of pictures of rapid motion Q)Oscillograpb Camera. It consists, essentially,
and yet each picture must have a short exposure ~f a delicate mirror galvanometers, a tuning fork
time. The ,requirement is not so much for high vibrating at a known high frequency, and a
repetition rate as for a series of high quality photographic app for recording time & galvanometers
images of the event during a reasonably long time deflection. Oscillograph cameras have been used
lapse, For these purposes a “stroboscopic light in conjunction with a “solenoid chronograph” for
source” is very suitable (Ref 18,P 52). An precisely measuring velocities of projectiles as
Intermittent light source camera employed at NOL described in Ref 4,pp 90-1 (See also Ref l,p 83;
(Naval Ordnance Laboratory), White Oak,Md for Ref 2,pp 163-5 and Ref 3)
study of underwater explns is described in Ref R) Photoelectric Celi Camera A camera using a
15b,p 104 photoelectric cell as a source of illumination,
P )Kerr- Cell Camera. The discovery of Kerr in These cameras may be used to study the following
1875, that when a transparent isotroPic substance ballistic problems: a)Detn of duration and
(such as glass, water or tiitrobenzene) is exposed intensity of a muzzle flash b)Time of burning of a
to a strong electric field, it becomes doubly fuse and c)Velociry of a projectile. In the study
-refractive, is utilized in construction of this of problems (a) and (b), the light produced by the
camera. The phenomenon discovered by Kerr is event impinges on a photoelectric cell thus
known as “electron-optical Kerr effect” or simply causing an elec current to be produced. In the
as “Kerr-effect”. This effect can be measured by study of probIem (c) the camera (such as used at
means of a “Kerr-cell”, also known as “electro Aberdeen Proving Ground), is so constructed chat
-optical shutter”. It consists of a transparent when the proj passes overhead, the reduction in
enclosure contg two plates attached at a slight light which impinges on the cell is recorded, by
ande to each other and immersed in nitrobenzene means of an amplifier, on an ‘~oscillograph” or on
medium, which is isotropic under ordinary conditions. another instmment. This method was found
In operation, the cell is placed between crossed especially suitable for measuring velocities of
polarizer inclined at an angle to the electric field Large caliber projs because they are fired at angles
consisting of two electrodes. Upon pulsating the of elevation Coo great for convenient use of
electrodes, the isotropic medium(nittobenz) “solenoid” or other types of chronographs (Ref 2,
becomes anisotropic and the polarized light ii pp 168 -71; Ref 9 and Addnl Refs a & b)
rotated due to the difference in the velocity of the S)Radiography of HighSp eed Events. See X-Ray
components paralled and normal to the field. The High-Speed Photography
amt of-rotation is proportional to the length of the T)Re/lected L igbt Photography. Any method in
path and to the applied field strength. The which a photograph is taken by reflected light
exposure time of a Kerr-ceil depends on the (such as flash or spark photography) may be so
duration of the pulse and can be as short as 10-9 c al led. The reflected light method requires, in
sec. However, the light transmission thtw general, more energy and longer exposure time
such a cell is only 7 to 15% (Ref 14a; Ref18*pp than the “shadow’ $ or “silhouette” method (Ref
77-8 and Ref 32) 21, v 17,p 811)
One of the first cameras applying Kerr-cell U)Rotating Drum Camera. See under Drum Camera
to study balIistic problems was designed by V) Rotating Lens Ring Camera. See Ref 31 ,pp.
Deutsch (ca 1930). His app was modified in 1932 350-4
by Cranz, Kutterer & Schardin to become known as W)Rotating Mirror Camera. See under Dmm Camera
“Kerreffekt- Chronograph” (Ref 2,P 165)* Kerpcell X) Rotating Prism Camera. See under Drum Camera
camera proved to be useful for photographing Y).$cblieren Method Cameru. “Schlieren” is the
highly s eii iumi.: ous effects, such as detonations Ger word for “striae” or “streaks” which are
 I

C 16

caused by regions of nonunifrom refraction in function of time. In the “Streak Camera”, such
gases, liquids or solids. This phenomenon was as developed by the US National Research
first observed in 1859 by J. Foucault of France Council (Ref 31,p 303), image of the object to be
who designed a test, called a “knife-edge test”, photographed is focused on the film plane. The
based on this phenomenon. The test was improved image or film may be moved at a controlled rate so
in 1864 by A. T6pler (Germany) who coined the as to produce on the film the “streaked” photo,
name “Schlieren-Methode” (Ref I,pp 258- 63; Ref which can be used to calculate the velocity of the
2,p 175 and Ref 18,pp 109 -18) object under srudy. For example, a luminous
E.Mach of Austria (1887) and later (1892) cylindrical shock wave expanding from a point
his son L.Mach were the first to apply the source would form a triangular image on a
‘ fSchlieren-Method” to study ballistic problems. streak-camera film, the slope of the edge of the
Since then the techniques have been improved image being proportional to the velocity of the
and the method is used extensively wherever it is shock wave. Beard (Ref 15a,pp 99-101) gives
required to study photographically rapidly description of the “Streak Detonating Camera”,
changing disturbances which cause refractive installed ca 1949 at NOL, White Oak,Md,
index changes in the air, or in other media in ‘ ‘Sweeping Image Cameras” are discussed in
which disturbance takes place (Ref 31,pp 324,497 & Ref 25,p 289; Ref 30a and Ref 31,pp 309-17 &
508). The combined “schlieren-interferometric 319-21. The principal part of these cameras is
method” is described in Ref 31,pp 525–9 the optical train which consists of a collimator
Z)Shadow (or Silhouette) Camera. In this method lens (which renders the light from the image points
invented ca 1880 by Dvorak, the shadow of a into paralled beams), a rotating mirror (which
small object (such as a bullet), moving at a high sweeps these beams into an arc) and a box camera
velocity betw a pulsed short-duration point light (which is set at infinite focus to receive the
source and a stationary photograpaphic plate (or reflected beams). The ‘*sweeping light beams”
film) is recorded on the plate (or film). The form. images which move across the film plane
distance of the plate (or film) from the light while, at the same time, remaining in sharp focus
source should be large in relation to its distance Notes: a) Liddiard (Ref 31,p 328) states that, as
from the object in order to avoid diffraction far as he knows, the terms “smear”, “streak” and
effects. Alternatively, a condenser may be used C‘sweeping image” are used interchangeably. In
betw the spark & the object NOL, White Oak,Md, they prefer to use the term
Accdg to C. Cranz [SS 9, 61(1914)] , BOYS “smear” to emphasize the fact that the photo
of England was the first to apply the shadow cont~ins a series of “smears” as against the
method to study ballistic problems (1893) and ‘ ‘portrait” type of photo obtained with “framing”
later, the method was used by E.Mach (Ref 18,p cameras b)Veagh (Ref 3 l,p 328) states that at
108) ARDE, England, the term “graph-drawing machine”
A short description of shadowgraphy of is used for “streak” or ~~smear” camera c)
bullets, utilizing sparks as the source of light is Chesterman (Ref 18,p 85), calls “portrait type”
given in Ref 21,p 169 images “discrete” which would suggest the term
In addn to shadow photographs taken with “indiscrete” for “smear-type” images
visible light, there are shadowgraphs taken with CC)Spark Cinematography. See Stationary Film
X-Rays (See Ref 14b and under X-Ray High Speed with Multiple Spark Camera
Photography) DD)Spark Photography, When it is required to
Shadow method may be combined with other have a source of light of brief duration (below 1
methods, such as with ‘ %chlieren-Method” (See microsec) an elec spark in air (or in inert gas) is
also Ref 25,p 81; Ref 31,PP 209, 369, 508 & 530 used. Sparks may be used in ‘ ‘Shadow”,
and Addnl Refs c & bb) “‘Schlieren” and “Interferometric” techniques
A A] Silhouette photography. See Shadow The spark produced by a Leyden j ar was the
Photography earliest light source used for the study of rapid
B B)Smear Camera; Streak Camera and Sweeping events by photography (F. Talbot in 1851). This
image Camera Accdg to definition given in Ref type of spark was first applied to ballistic
31,p 322, a “Smear Camera” is an instrument investigations in 1884 by E.Mach & P .Salcher. In
which records continuously (as contrasted with later cameras, a spark was produced by electronic
intermittent recording of a ‘ ‘framing camera”), the or other devices, such as “guided spark
changes of light intensity along a line as a flashlamp”, etc (See Ref l,pp 258-9 & 349-62;

... ....——— —————.—

 c 17

Ref 2,pp 176-93; Ref 18,pp 17& 105; Ref 21, vol Note: Accdg to Chesterman (Ref 18,p 33),
21,p 169; Ref 25,p62; Ref 29,pp 102-7 and Ref “stroboscopic” is not, strictly speaking, a
31,PP 11,13,17,41,369,489 & 498)(Compare with correct term for the camera so named, because
Flash Photography) C‘strobo scope “ is an instrument for observing the
EE)Speediigbt or Speedlamp Photography. It successive phases of a periodic motion by means
utilizes the light from the discharge of a charged of a light periodically interrupted, The early
electrical condenser or capacitor thru a tube ~~stroboscopes” used mechanical modulation of
(glass, Pyrex or quarz), provided with metallic the light, but with the development of gas
end electrodes and filled with gas (such as argon) discharge, the successive flashes of the light
which has the property to fluoresce momentarily have been achieved electrically, When these
to a high brillance. Devices producing flashing light sources began to be used as
“speedlight” are known commercially as photographic illuminants, they were often loosely
“Speedlamp”, “Speedflash”, “Electronic Flash”, termed “power stroboscopes”
etc. A “Speedlamp” gives only one short flash II)Sweeping Image Camera, See under Smear
every time the current is switched on, and should Camera; Streak Camera and Sweeping Image
not be confused with ‘tStroboscope”, which Camera
flashes repeatedly at short intervals (See Refs ]])X-Ray High Speed photography or
7, 12 & 29) Radiography of High Speed Events. When an
FF)Stationary Fi~m with Multiple Spark camera or optical method cannot be applied (either due to
Spark Cinematography. It is employed for the event being accompanied by an intense light
extremely rapid events (such as at R=240000fps flash sufficient to obliterate the effect under
or as high as 106), when tin; techniques and study), one usually resorts to ‘~X-Ray
drum cameras prove to be unapplicable to moving P holography”, also known as ‘ ‘Radiography”.
films at such high speeds. With this camera a In this method, a burst of x-rays of great
limited number of discrete images are formed intensity and of over-all time duration of the
successively on a stationary film (or order of 1 microsec or less, is utilized to
photographic plate) by means of a series of produce shadow radiographs of objects which are
illuminating gaps discharged in very rapid either completely ‘or partially optically opaque
succession (Ref 1,pp 349-62; Ref 2,pp 1.86-93 and (such as bullets, metal fragments in
Ref 18,p 15) detonation products, etc). One of the important
GG)Streak Camera. See Smear Camera, Streak applications of x-ray techniques is investigation
Camera and Sweeping Image Camera of behavior of conical metallic linings during
HH)Stroboscopic Camera (from the Greek word detonation of shaped charges. Here the light
“strobo” meaning ~‘intermittence”). In this emitted by linings is rather weak in comparison
camera is utilized a lamp (such as neon-filled with the flash produced on deton of HE chges and
“thyratron”) which produces extremely short in photographs by optical methods (except
flashes of light repeated in rapid succession, the Kerr-Cell techniques), only the latter flash is
timing of which is instigated by the camera visible (Ref 18a and Addnl Ref c ). Other
mechanism. The camera, itself, is shutterless applications of x-ray techniques to ballistic
and has merely the function of transporting the problems are discussed in Refs 14c, 18, 25, 25a,
film continuously at a high rate thru the mechanism, 31 and Addnl Ref f)(See also Ref 22)
and the extremely brief duration of the flash Note: Cook (Ref 25a,p 23) gives a table listing
c‘arrests” the motion of the film during photography high-speed cameras presently employed in
of the event. These cameras can be utilized to detonation studies. Three types of cameras are
make either multi-exposures on one film (showing listed: “streak”, “single-frame” and
progression of some motion) or to slow down, or ~‘multiple-framing”. Of these, Cook considers
to stop an apparently repetitive motion. They the “streak camera” as ‘{a work horse” of the
also can be synchronized with motion picture modern explosives laboratory, along with the
cameras to produce t ‘slow motion picture “pin oscillograph” and the C~rotating-mirror
Stroboscopic cameras” framing camera”
Stroboscopic cameras have been extensively The section on “Cameras, High-Speed,
used for solving ballistic problems (See Ref l,p Photographic” was reviewed by F. R. Schwartz of
341; Ref 2,P 159; Refs 6,10,11,13,17,18,19,25, P icArsn, Dover, NJ
26,29,31 and Addnl Ref 1) Re/s: l) Cranz vol 3(1927), 83, 257-67 & 384-408
 C 18

(Ballistic photography) 2)Cranz, Erganzungsband K .Shaftan, g‘High-speed Photography”, pp 201-30

( 1936), 163-93(Suppl to material of vol 3) 3) in “Progress of Photography 1940-1950”, Focal
J .T.McGregor-Morris, “Cathode-RaY Press, London( 1951) 20)C.Candler, “Modem
Oscillography”, Chapman & Hall, London (1936) Interferometers”, Hilger & Watts, London(1951)
4)Hayes( 1938), 90-l(Oscillograph camera in 20a) F.D.Bennett et al, JApplPhys 23, 453-69
ballistics) 5) J. E.Mack & M.J .Martin, “The (1952)(ca 20refs) 21)EncyclBritannica 15(1952),
Photographic Process”, McGraw-Hill, NY( 1939) 854-7o (Motion picture cameras); 17(1952), 811
6)J. E. Mack, “Stroboscopic Photography”, (High-Speed Photography under Photography) and
McGraw-Hill, NY(1939) 6a)H.E.Edgerton, “Flash’; 21(1952), 169( Spark photography) 22)
Hale, Cushman & FIint, London(1939) 7) H .R.Clauser, “Practical Radiography for
H.E .Edgerton, “Speedlamp Photography”, Morgan & Industry”, Reinhold, NY(1952), 279-83(High-
Lester, NY(1$42) 8)C. Tuttle, “High-Speed speed photography by means of x-rays) 22a)
Photography”, Morgan & Lester, NY( 1944) 9) G .A.Jones, “High-Speed Photography”, Wiley, NY
V. K. Zworykm & E. D. Wilson, “Photocells and (1952) 23)CO11, t ‘High-Speed Photography”,
Their Application”, Wiley, NY( 1945) 10) SocMotPictEngrs, NY, vol 1(1952), vol 2(1952),
R. C. Walker, “Electronic Equipment”, ChemPubg- Vol 3(1953), Vol 4(1954) & Vol 5(1954) (Vol 5
Co, Brooklyn(1945), 105(Stroboscopic camera) 11) contains papers presented at the First
G. M. Chute, “Electronics in Industry”, McGraw- International Congress of High-Speed
Hill, NY(1946)(Stroboscopic cameras) 12) Photography) 23a)J .S.Courtney-Pratt, JPhotoSci
A.Palme, ‘ CSpeedlights, Construction and Use”, 1, 21(1953)(Fast multiple-frame photography) 23b)
AmerPhotogPubgCo, Boston( 1946) 12a) R. T. Knapp, J. H. Waddell & J. W. Waddell, Industrial Laboratory
JSocMotpictEngrs 49, 64-82(July 1947) 13) 1954, Feb, pp 95-103; May, 95-102; June, 93-108;
Westinghouse Electric Corp, “Industrial Electronics Sept, 67-74 & Ott 105-12( Photographic motion
Reference Book”, McGraw-Hill, NY(1948), 420 picture analysis) 23c)J.H.Ruiter, “Modern
(Stroboscopic camera) 13a)T.Soler, Edit, Oscilloscopes and Their Uses”, Reinhold, NY
‘ ‘Cathode Ray Tubes Display”, McGraw-Hill, NY ( 1955) 24)C011, “Proceedings of the Second
( 1948) 14)H.K. Bourne, “Discharge Lamps for International Congress of High-Speed
Photography and Projection”, Chapman & Hall, Photography”, Dunod, Paris( 1956) 25)COU,
London( 1248) 14a)A.M.Zarem et al, ElecEng 68, “Proc Third Intnl Congr High-Speed Photog”
No 4, 282-fi1949)(Kerr-cell) 14b)B.O’Brien & Butterworth, London(l 957) 25a)Cook( 1958),
G. Milne, JSocMotPictEngrs 52, 30-41( Jan 1949) 22-43 25b)C.M.Huggins, JSocMotPictTelevEngrs
(Motion picture photography at 10 million frames 67, 523-6(1 958)(Analytical evaluation of the
per second) 14c)C,M.Slack et al, Ibid 52, 61-70 lenticular plate cinematography and the image
(March 1949)(X-ray motion pictures 15) -dissection process) 25c)A.Haas, “Oscilloscope
C. H. S. Tupholme, “Photography in EngineeringS’, Techniques”, Gernsback Library, NY( 1958) 26)
ChemPdbgCo, Brooklyn( 1949), 99-13(High-speed Coil, “ProcFourthIntl Congr High-Speed Photog”,
photography) 15a)M.Beard, JSocMotPictEngrs 52, Verlag Helwich, Darmstadt( 1959) 27) G. J. Wolffinden,
97-9( M~rch 1949)( Cathode ray oscillograph “Hypervelocity-Data Recordings Study”, Aerojet
camera) 15b)M. Beard, Ibid 52, 99-10 I & 104-6 Repofi 1541( Final), Feb 1959; APGC-TR
(Match ~1949)(Intermittent light camera and rotating 59=33(1); ASTIA Document AD 216295 27a)
‘prism Camera 16) F. Fayolle & P. Naslin, J .L.Squier & G. J. Wolffinden, “Hypervelocity
‘ ‘Photographic Instantann6e et Cinematographic -Data Recording Study (Bibliography)”, Aerojet
Ultra-Rapide”, Institut d’Optique, Paris(1950) 17) Rept 1541 (Supplement), Feb 1959 28) W. G. Chase &
P. G. Andres, “Survey of Modern Electronics”, H. K. Moore, “Exploding Wires”, Plenum Press, NY
Wiley, NY( 1950), 33-6(Stroboscopic camera) 17b) (1959) 29)R.L,Aspden/gElectronic Flash
M.Sultanoff, RevSciInstr 21, 653-6( 1950)(A 100 Photography”, Temple Press, London (1959) 30)
million frame-per second camera) 17c)J. F. Rider & C. H. Elmer, Edit, “Instrumentation and High-Speed
S. D. Uslan, ‘ ‘Encyclopedia on Cathode-Ray Photography”, SocMotPictTelevEngrs, NY, VOI 1
Oscilloscopes and Their Uses”, Rider (1960) 30a)B.Brixner, JourSocMotPictTelevEngrs
Publisher, Inc, NY( 1950) 18)W.D.Chesterman, 69, 109-12(Feb 1960) 31)Coll, “ProcFifthIntnl
‘ ‘Photographic Study of Rapid Events”, CongrHigh-Speed Photog”, SocMotPictTelevEngrs,
Clarendon Press, Oxford, England(1951) 18a) NY( 1962) 32)F.R.Schwartz, PicArsn, Dover, NJ;
E.M.Pugh et al, JApplPhys 22, 487-93(1951) 19) private communicatiori (1962) 33)F.R.Schwartz,
 c 19

“High-SpeedP holographic Facility for Study of detonation in cones of expls) aa)I. T. Okawa,
Detonation’’, (Presented at the 14th Meeting of JIndExplsSoc, Japan 13, 247-54(1952)&CA 49,
PicArsnScientificAdvisory Council, on April 26, 5841{ 1955)(Study of muzzle-flash by high-speed
1957)(ConfidentiaI; not used as a source of info) photography) bb)P.Liebessart, Science et
Addrd Refs: a) E.M.Shinkle, ArOrdn 11, 93-1,00 Industries Photographiques 23, 14-16(1952) & CA
( 1930)(High-speed photography for testing 46, 6533( 1952) (Sbadow photographic study of
weapons) b) P. Bernard, MAF 12, 425( 1933)( Use of combustion of detonating cords) cc)RoyaI
photo-cells in ballistics) c)W.Payman & Photographic Society of Great Britian,
D. W. Woodhead, MAF 12, 741(1933) [High-speed ‘ ‘Photography in Science and industry”, London
photography (including “Schlieren” & ‘ ‘Shadow” ( 1952) dd)F.D.Bennett et al, JApplPhys 23,
methods) in ballistics] d) A. Magnan, 453-69( 1952)(Interferometric method) ee)
“Cin6matographie Ultra-Rapide”, Hermann, Paris G. D.Kahl & F. D. Bennett, Ibid, 763-7(Mach-Zehnder
(1933) e)H.E.Edgerton, TransAmInstElecEngrs interferometer) ff)M.Lorant, Functional Photog 5,
54, 149-53( 1935)(High-speed motion pictures) f) 4-6( March 1954)( New photographic techniques in
C. M.Slack & L. F. Ehrke, JApplPhys 12, 165-8 HE research) gg)M.Sultanoff & R. L. Jameson,
( 1941)(X-ray high-speed photography) g) J. L. Boon, JSocMotPictTelevEngrs 69, 113-15 (1960)(New
JSocMotPictEngrs 43, 321-7( 1944)(Eastman observations of expl phenomena by
high-speed camera, Type III) h)M.P.Vanyukov, s ubmicrosecond coIor photography)
ZhTekhnFiz 16, 88 9-92(1946) & CA 41, 1106
( 1947)(A device for photographing explns) Camouflet. When a missile has penetrated so deep
i)W.W.McCormick et al, JApplPhys 19,221- 5(1948) Iy into the ground that no surface effect resuIts
“(A microflash unit for ballis~ic photography) j) from the expln, but instead a rough spherical
D. Croney, Nature 160, 490-1(1948) & CA 43, cavity is formed be bw ground level, the cavity is
3 197(1949 )( High-speed mirror camera for photogra- called camouflet. This term is also applied to the
phing the process of luminous detonation front explosive that makes such cavity (See also under
inside transparent liquid expls) k)H. E. Edgerton, Blast Effect in Earth)
JSocMotPictEngrs 52, 8-23( March 1949)(Elec This is also applied to a military demo-
flash photography) l)K.J.Germeshausen, Ibid, lition chge used by the defenders to destroy the
24-34(March 1949) m)M.Beard, ibid, 99-101 attackers’ mine-galleries without breaking t’~e
(Streak detonation camera) n)M.Bead, Ibid 105-6 surface of the earth. If the surface is broken the
(Rotation prism camera) o)J.C.Clark, JApplPhys resulting crater might become a shelter for
20, 363-7o( 1949) (Flash radiography applied to a ssatd ting troops which is not desirable from the
ordnance problems) p)D.K.Weimer et ai, Ibid 418 point of view of defenders (Ref 1)
(Interferometric camera) q)W.T.WheIan et al, R e/s: l) EncyclBritannica 4(1952), 672 2)Anon,
JSocMotPictEngrs 52, 116-29(March 1949) ‘ ‘Military Explosives”, TM %1910(1955), 77 3)
(Electronic flash Iighting) r)V.E.Bergdolt et al, C.Randall, “Camouflet Experiments in Ice”,
PhysRev 76, 879( 1949)( Interferometric method in NavOrd Rept 4548( 1958)(Conf)(Not used as a
ballistics) s)F.D.Bennett & W. C. Carter, Ibid 880 source of info 5)Gfossary of Ord( 1959), 54 5)
(Interferometric method in ballistics) t)H.F.Quinn Merriam-Webster’ s(1961), 322
et al, JApplPhys 21, 995-1001( 1950) (Kerr-celI
camera and flash illumination unit for ballistic 2. Camphanone. Same as Camphor
photography) u)C.A.Adams, PrRoySoc 204A, 19-20
( 1950)( Optical streak cameras for observation of Camphene and Derivatives
explns on the field-trial scale) v) G. K. Ashford et
al, JChemPhys 18, 1 I 12-13( 1950)(Detn of burning Carnpbene { called 2.2-Dimethyl-3-methylen
velocities from shadow and direct photographs of a -bicycle- [ 1.2.2] -heptan in Beil}, Cl ~H1 ~, mw
flame) w)A.J.Zaehringer, Rocketscience 4, 65-6 136.23; CO1 trysts, mp ca 50°. Other props &
( 1950)( Flame photography of BkPdr) x) J.S.Courtney prepn in Beil 5, 156, (82) & [105] . Used for
-Pratt, ProRoySoc 204A, 27-9( 1950)( High-speed manuf of synthetic camphor and as camphor
photography using as a light source detonation of substitute
LA) y)E.M.Pugh et al, JApplphys 22, 487-93 Nitrocamphenes, CIOH1 ~N02; mw 181.23,
( 1951 )(Kerr-cell photography of rapid events) z) N 7.73%. Three forms are described in the
D.W.Woodhead & R. Wilson, Nature 167, 565-6 literature: a)u-Nit?ocam@ene, called
(Rotating camera for investigation of “fading” of
 c 20

“‘Camphenilnitrit” by W. Jagelki [Ref l,pp 161, Fr, Campher in Ger, Canfora in Ital, Alcanfor in
(85) & Re 2] lt yel ndls(from Iigroin), mp 65°; Span & Kamfora in RUS) ~ called l.7.7-Trimethyl
puffs off at higher temps; can be prepd by heating -bicyclo - [ 1.2.2] -.heptanon- (2) in Beil},
camphene with dil nitric acid or by other methods
d)l-Nitrocarnphene prisms (from ale), mp 56°; was
prepd by heating under reflux an alc soln of I; H2;–~(CH3)—~0
1 -bromonitrocamphene with powd Ag nitrate 1Ref ;
7$(CH3)*
l,pp 166, (88) & Ref 3] c)6-Nitnxarnpherze or
sec-~Camphene, oil, bp 119-119.5 at 14mm; was HzC—CH——————CH2
54 3
obtained (together with other products) on heating,
CO1 or wh tryst plates, easily broken when moist-
in a sealed tube at 125-130°, tricyclene,
ened with ether; mp 174-9°, bp 209.1 at 759 mm
C, OH, ~(a tricyclic terpene) and nitric acid
fl p 82°; slowly volatilizes in air at RT; d 0.992
(d 1.075) {Ref l,p [108] and Ref 4}
at 250/i; nearly insoI in w; sol in ale, eth, chlf,
Re/s: l)Beil 5, 161, 166, (85,88) & [108]
CS2, solvent naphtha and fixed & volatile. oils.
2)W.Jagelki, Ber 32, 1499( 1899) 3)M.O. Forster,
Can be obtained by distilling chips from, the camp-
J CS 79, 646-7(1901) 4)S.Nametkin & A. Zabrodina,
hor tree(cinamonum camphora), native of Formosa,
Am 441, 185(1925)
China, Japan, Malaya, Archipelago & Brazil and
Campbene@trosite, Cl OH, ~N203(?) grn oil,
now cultivated in Florida and California; can be
decomp ca 500 during distn in vacuum; was
prepd synthetically by one of the methods describ-
obtained by J agelki, together with other products,
ed in Refs 1, 5, 7, 8, 11, 12, 13)
on treating camphene with nitrous acid in
Camphor is flammable and toxic when
ligroin. Its Potassium salt, KCtoH1 ~N203, red
taken internally. It gives off flammable vapors
ctysts (from ale), puffs off on heating
when heated, which may form expl mixts with air
Re/s: l)Beil 5, 161 2)W.Jagelki, Ber 32, 1502(1899)
(Ref 12). Sax(Ref 16) gives explosion range in
Carnphenerzitro;itrosite, Cl OH, ~N305(?) wh air as 0.6 to 3.57. by wt of camphor, while Jono
pdt; mp dec ca 149°; W~S obtained b JweW (Ref 15) gives 6 to 26% depending on conditions
together with other products on prolonged of testing. Toxicology of camphor is breifly
treating of camphene with nitrous acid in discussed by Sax(Ref 16)
Iigroin Uses: Camphor, being a good plasticizer for NC,
Re/s: l)Beil 5, 161 2)W.Jagelki; Ber 32, 1501 is used in celluloids & other NC contg plastics.
(1899) It is used in smokeless proplnts as a plasticizer,
5-Nitroso-5-nitrocamphene or Camphenepseudo- and as stabilizer & flash reducing agent. It has
rzitrole, C10H14N203, mw 210.23, N 13.33%; been used also in some dynamites (as desensitiz-
IfIts(from chlf), mp 99° with decompn; was er), BlkP drs (as binder), and in some pyrotechnic
prepd by treating 6-nitrocamphene( see above) compns. Camphor is now used in the following US
in cold, dil NaOH soln with Na nitrite and dil plastic compns (Celluloids or Pyroxylin Types):
sulfuric acid a)composition A, prepd by mixing NC (ca I I z
Re/.s: l)Beil 5, [108] 2)S.Nametkin & N) 3 par% cmphor 1P, urea 0.75+0.05%
A.2abrodina, Ann 441, 186(1925) of NC & solvent in amt sufficient for processing;
Campbeneozonide, C , OH1 ~03, viscous oil; was it comes in sheets an d is intended for use in
prepd by treating camphene in chlf with ozone powder wads & spacers; and b)Composition B,
Re/s: l)Beil 5, 160 & (84) 2) F. W. Semmler, Ber consists of NC(ca 11% N) 72-78 & camphor
42, 247(1909) 28-22%; it comes in discs with vents intended
for use in fuses, tracers & primers(Ref 19)
Campher. Ger for Camphor
FoIlowing are examples of the uses of
camphor in propInts & expl compns of some other
Campherylazid. Ger for Camphorylazide (see
countries:
under Camphor and Derivatives)
Austria-Hungary-see Camphorated Blasting
Gelatin
Camphor and Derivatives
France-used camphor is some rifle proplnts,
Camphor, c1 OH, ~0, mw 152.23 ;exists in several such as BFP & BF~,(Ref 6)
forms, of which the most important is: d- Cumpbor
Germany-used camphor in some small arms proplnts.
or 2-Carrrpbanone or 2-Ketocam#bane (Gum-,
These proplnts were claimed to be progressive
Japan-, Formosa- or Laurel-Camphor)(Camphre in
burning because their core was gelatinized NC
 C21

of high N content, which was treated on the Addr.d R efs: a) W. R. Tomlinson,Jr, PATR 1151
surface with camphor w or w~ EtCentr(Ref 8a). (1942)(’ ‘Special Blasting Gelatin” developed by
Camphor was also used in some cannon prolnts Hercules Powder Co of Wilmington, Del contained:
(Ref 17) mixt of NG with Tetranitrodigly cerin 90, NC 4,
GtBritian-used camphor in some EC proplnts camphor 5 & chalk 1%. Its examination at PicArsn
(Ref 3) labs showed that it is an expl of high brisance
Italy-used a military demolition expl consisting and satisfactory stability, but very sensitive to
of 100ps of 92/8-BIasting Gelatin and 5ps of rifle bullets and impact tests. It has a low expln
camphor(Ref 4,p 310) temp and high volatility. Because of its
Russia used during WWI a “camphorated blasting sensitivity to rifle bullet and impact, it was
gelatin’’(which consisted of NG 90, collodion considered to offer little promise for military use,
cotton 6 & camphor 4%) for filling some trench such as for loading bombs) b)L.P ,Kyrides, USP
mortar shells. Cornpns of some camphor contg 2126560(1938) & CA 32, 7926( 1938)( Cyclohexyl-
cannon propbts are given in conf Ref 14 amine derivs as plasticizers for NC, substituting
Accdg to Nao6m(Ref 4,p 310) the camphor)
“camphorated blasting gelatin(such as Ital or Camphor, Analytical Procedures. As camphor is a
Rus) required a stronger inrial impulse. to ensure widely used compd, many procedures for its
derogation than that used for ordinary gelatin. In detection and determination in commercial products
some cases one was required to use stronger than have been developed. The general procedures are
No 8 cap(.see also Camphor, Analytical Proce- described in Refs 1,4,7 & 8, while other Refs deal
dures) with detn of camphor in expls and proplnts
Re/s: 1 )Beil 7, 101,(7;) & [93] 2)Marshall 1, Dalbert(Ref 11) who investigated existing
(1917), 338 & 3(1932), 98(Camphor in celluloid) methods of dern of camphor in proplnts, came to
3)Marshall 2(1917), 658 & 3(1932), 98( Camphor in the conclusion that the method of Desmaroux
smokeless proplrrts) 4)Nao~m, NG( 1928), 10 & ( Ref 3) was very rapid although not as accurate
31O 4a)J.Desmaoux, Mp 23, 54-62(1928) as “oximation~t methods described in Refs 5,6,9 &
(Fixation of camphor by NC) 5)Ullmann,3(1929), 10
60-82(Campher)(not found in new edition) 6) The “oximation” method was modified by
J .Desmaroux, MP 24, 282-4( 1930-l)(BaIlistic Dalbert to make it a semi-micro procedure which
stability of propInts contg camphor and is described below
centralizes such as the rifle proplnt BFP) 7) The apparatus consists of one 200-ml
,,Le Camphre et ces D~riv~s’ ‘r. round bottom flask (A), one 150-ml flask (C), one
R. Comubert,
Masson, Paris(1933) 8)1. Gubelman & H. W. EHey, 150-ml, two neck flask (B), a funnel (E) with
IEC 26, 589-94( 1934)(Amer production of stopcock (R), a trap and a reflux condenser for
synthetic camphor from turpentine) 8a)G.A. flask (C)(See Fig)
Hunold, sS34, 129(1939) 9)G.Komppa, Ber 75A,
1-13(1942) & CA 36, 6153( 1942)(A review with
62 refs of the work done by Kompa et al on the
synthesis of camphor and terpene compds) 10)
Davis(1943), 257-8, 289 & 293-4 ll)’CElsevier’s
Encyclopedia of Organic Chemistry”, ELsevier,
Amsterdam, series III, vol 12A(1948), 735-57 12)
Kirk & Othmer 2(1948), 808-18 13)V.Grignard et
al, “Trait6 de Chimie Organique”, Mass on,

U,:
Paris, VOI 16(1949) 209-69(580 refs) 13a)G.
Champetier & F.Boyer-Kavenoki, CR 234,1053
(1952)(Gelatinization or NC with camphor) 14)
PATR 2145( 1955),P RUS 18(Conf) 15)W.Jono, The reagents are: N/10 hydrochloric acid
soln; hydroxylamine hydrochloride, prepd by
JChemSocJapan 58, 673-5(1955)&CA 50,8027
dissolving 17.5g of NH20H.HC1 in mixt of 250ml
(1956)(Expln of camphor vapor or dust in air) 16)
alc & 25ml distd w; diethylaminoethenol, prepd
SSX(1957), 432 17)PATR 251 O(1958),P Ger 141
by dissolving 11 .7g of (CZH5 )2 N.CH2 .CH2 .OH in
17a)Merck(1960), 200-1 18)CondChemDict( 1961),
1000ml ale; bromophenolblue indicator, prepd by
210-11 19)uS Military Spec MIL-C-15567(BuOrd)
dissolving 0.02g of Cl ~Hl ~Br40sS in 100 ml alc
(Cellulose Nitrate Plastic, for use in ammo)
 c 22

Standardization Procedure. In order to det the gently for 2hrs under refIux condenser. g)cool the
coIor produced by a known amt of pure camphor, flask and pout its contents into a flat-bottom
boil gently for 2hrs in a fIask similar to (C), tube, 32mm diam used for calorimetric detns h)
provided with reflux condenser, a mixt of Proceed exactly as described in above in
accurately weighed pure camphor (20 to 30mg), “Standardization Procedure” , using a blank
1 Jml distd w, 10ml hydroxylamine hydrochloride Analytical procedures for camphor are also
reagent, exactly 10ml of diethylaminoethanol described in Ref 6a
reagent and a few piece’s of pumice stone. In the Refs:’ 1 )Beil 7, 108,(79) & [98] 2)M.Marqueyrol,
2nd flask boil a mixt of the same ingredients as AnnChimAnal, 16, 209-10(1912) & CA 6, 667
above, minus camphor (blank) (1912) (Apptox method for detn of camphor in a
The following reactions takes place with proplnt by loss of wt at 30-40° of ethereal
camphor in the Ist flask: extract previously dried over suIfuric acid) 3)
C9H, ~.C0+NH20H.HCl ——————+ J.Desmaroux, MP 23, 43-53(1928)& CA 22,
C9HI ~ .C:NOH+H20+HCI 3531( 1928)(Approx detn, of camphor in a propInt
by a method based on the
Cool both flasks and empty their contents
measurement of surface tension of an aq soln of
into two flat-bottom tubes, 32mm in diam. Bring
camphor removed from proplnt) 4) Ullmann, 3
the contents of each tube to the height of 70mm.
(1928), 81 5)R.Vandoni & G.Desseigne, BullFr
Prepare an approximate color standard by filling
[5] ,2, 1685-91(1935) &CA 30, 56(1936 )( For
another tube(the 3rd one) to the height of 70mm
volumetric detn of camphor in a proplnt or an expl
with the green soln prepd by mixing 50ml of 2%
by the hydroxylamine method, proceed as follows:
soln of Ni sulfate with 5ml of 1% soln of K
Introduce into a 100ml flask 50ml of 2N
chromate. Add to the contents of the Ist and 2nd
hydroxylamine hydrochloride, 0.2ml of bromophenol
tubes lml of bromophenolindicator and titrate the
blue indicator and bring to the neutral tint. Add
1st tube with std N/10 HCI until the color
exactly lg of pure Ca carbonate and l-2g of test
approximately matches that in the 3rd tube. Add
sample. Boil on a water bath with a reflux
to the contents of the 2nd tube std N/10 HC1
condenser and then cool to 30°. The soln should
until the color matches exactly the color in the
remain alkaline to the indicator, Add a measured
1st tube. The amt of camphor placed in the 2nd
VOI of std HC1 until all Ca carbonate dissolves
flask is calcd from the formula
and finalIy titrate with N/l NaOH soln. The
(R’-R”) x 15.2 where R’ is burette reading
results were claimed to be accurate to within 1%
for the 1st tube, R“ for the 2nd tube and 15.2 is
of actual camphor content) 6)G,A .Hunold, SS
empirical constant
34, 129-31(1939) &CA 33, 7113(1939)
Analysis of Sample
(Modification of method of Vandoni & Desseigne
a) Place in the flask (A) of apparatus(see Fig), ca
which was briefly described in Ref 5) 6a)Kast
2g of accurately weighed proplnt(in small grains),
-Metz( 1944) 151-9( Props & tests) 7)Kirk &
15ml NaOH soln(36°B4), 100ml distd w, 2ml alc &
Othmer 2(1948), 815(Specifications for camphor
a few pieces of pumice stone. Close the flask
and required tests) 8)’ CElsevier’s Encyclopedia
b) Place in the flask (B) 20ml distd w, lml
of Organic Chemistry”, Ekevier, Amsterdam, vol
sulfuric acid & a few pieces of graunlated Zn. Make
12A, seriesIII(1948), 754-5 (General analytical
connections to flasks (A) and (C) as shown in
procedures for camphor) 9)H.Liogier, MP 30,
Fig and Ieave stopcock (R) open c) Bring the
269-71( 1948)(Detn of camphor in smokeless
contents of (A) to boiling in order to saponify the
proplnts by the method of oximation) 10)G.
proplnt and continue boiling until ca 60ml of
F1eury & B.d’Estivaux, MP 30, 273-6( 1948)(Detn
liquid distls into flask (B) d)Rinse the funnel (E)
of camphor in rifle proplnt BFP, ) 1 l)R.Dalbert,
with 3ml of alc, close stopcock (R) and boil the
MP 30, 277-82(1948) & CA -not found(Detn of
contents of (B) until ca 20ml of distillate collects
camphor in proplnts) 12)’ ‘Organic Analysis”,
in flask (C) e)Remove the stopper with the tube
Interscience, NY, vols ~-4( f953-1960)-no anal
from the upper part of condenser and pour thru the
procedures for camphor are given
condenser ca 10mI of aIc f) For oximation of
camphor contained in the distillate of flask(C), 3-Azido-d-camphor or Camphorylazide(called
introduce 10ml of hycfroxyIamine hydrochloride Camphorylazoimide by Forster & Fierz and
reagent, 10ml of diethylaminoethanol reagent, a a -Triazo-d-campher in B eil),
$ew pieces of pumice stone and boil the mixt
 C23

Re/s: l)Beil 7, (332) 2)M.O.Forster et al,

co
JCS 99, 1989-90(1911)
‘W: / ;
“CH.N3 Diazocamphor, Cl OH, 4NZ0, mw 178.23, N
15.72%. The isomer 3-Diazo-d-camphor,
mw 193.24, N 21.75%; transparent, hexagonal co
prisms, (from ale) mp 67°; mildly expl at higher /
CeH14 I
temps and readily volatile with steam; mod sol in
~:N2
boiling w & in cold abs SIC; sol in ethyl acetate,
acet & petr ether. Can be prepd by treating a orange-.yel trysts (fran petr eth), mp 75°; can be
cold aq sokt of camphoryl-~ semicarbazide prepd by diazotization of a-aminocamphor with Na
nitrate,C,,H,~N302 [ called Pseudo-campheryl nitrite in cold inorganic acid (Ref 1) or by other
-semicarbazid-nitrat’”in Ger-see Beil 25, 22 & methods (Ref 2)) Its expl props were not reported
(467)], with Na nitrite Re/s.’ l)Beil 7,(332) & [557] 2) W. A. Noyes & E.
R efs: l)Beil 7,133 2)M.0. Forster & H. E. Fierz & Meitzner, JACS 54,3768-73(1932) & CA 26,5296
JCS 87,830(1905) 3)CA-not found in years 1907 (1932)
thru 1956
Mononitrocamphor,C ,oHfsN03, mw 197.23, N7.1O%; Camphorated Blasting Gelatin. A compn consist-
exists in two forms: 3-Nitro-d-camphor or a ing of 90/10 Blasting Gelatin 96 and camphor 4%
-Nitro-d-camphor, , col prisms(from was used in Austria- Hungary as a military blast-,
c H /-co
8 14 ing explosive. It was replaced in 1892 by Ekrasit
I
“CH.N02 (Ecrasite)
Ref: Naotim, NG (1928),310
benz), mp 100-3°. Other props & preprt in Ref 1;
iso--Nitro-.d- camphor (aci- Form), Camphoric Acid and Derivatives
co Camphoric Acid (CamphersSure in Ger), Cl OH, ~04;
C H ~~o or CH>I ; mw 200.23. Several isomers and forms are
8 “>c/l * 14=C:N02H
\N.OH described in Beil 9, 745,760,(324,332) &
was not isolated in pure state. Forms numerous [534,5391
salts d-Camphoric Acid Peracid,
Re/s: ljBeil 7,128(83) & [ 103] 2)Beil 7,129,(83- H2C-$(CH3)-COOH(tert)
4) & [1031 I $(CH,J2
Dinitro- , C , OH, 4N20~; Trinitro-, Cl ~H1 ~N307 H2C–CH ‘C(:O).O.OH(sec)
and Tetranitrocamph ors, C 10H1 ~N409 were not mw 216.23, active O -7.40%; wh solid, mp 49-.50°
found in Beil or in CA thru 1956 (in a sealed tube); expl when heated to 80- 100°;
iso-Nitrosocarn pbor, fairly stable at 0° in dry air, but slowly dec at RT,
Oximinocampbor or Campborquinoneoxime, sol in w(hydrolyzes in dil solns); SI sol in petr
C10H15N02, mw 181.23, N 7.73%. Several eth; sol in nearly all org soIvents; was prepd by
isomers and forms are described in Beil 7, 583, treating an ethereal soln of d- camphoric anhydride
584, 585, (325, 327) & [553,554,5551 with, Na peroxide in w at 0°
Per rzitrosoccimpbor, Cl OH, sNz02, mw 196.24, N Note: When using smalIer quantity of Na peroxide
14.28%. Several isomers and forms are described Di$amphoryl Peroxide is obtained
in Beil 7,115, 136,(81, 85) & [99] R efs: l)Beil -not found 2)N.A.Milas & A. McAlevy
Pernitrosoisonitrosocamphor or Camphorquinone JACS 55,349- 50(1933),
oxime Nitrimine C,oHl ~N303, mw 225.24, N
18.66%. Its isomer called [d-Campher] -chinon Camphor Oil. A constituent of crude camphor. It
-oxim-(3)-nitrimin- (2) in Beil,
is usually separated into two fractions: a)Red
C:N*02
ceH,: Oil(also called Brown or Heavy Oil), contains
, ndls (from dil ale), mp
\ fractions boiling betw 210 & 250°. Its d is 1.00
‘e:N.OH to 1.04, fl p ca 1060C and the principal
147.5°, was obtained by treating K salt of constituents are: terpineol, camphor, safrole,
~pernitrosocamphod’ suspended in dry ether with sequiterpene hydrocarbons and alcohols b) Wbite
nitros ylchloride gas until the liq became yel. or Light Oil, contains fractions boiling betw 160 &
Its expl props were not reported 185°. Its d is .870’to .875, fl p ca 48°and the
 C24

principal constituents are: terpenes, cineol with ea, native of Canada & Maine. It dries in the air
small amts of terpineol, borneol and camphor(Ref to a transparent resin which has a refractive index
1) equal to that of glass. Hence, it is used to cement
According to Ref 2, camphor oil is a CO1, lenses together, to mount microscopic specimens,
natural oil with characteristic odor, d 0.870 and as a varnish
-1.040, n~ 1.465-1.481 at 20°; sol in eth, chlf; Re/: Hackh’s (1944), 162-3
insol in ale; its chief constituents are pinene,
camphor, cineol, phellandrene, dipentene, Candelilla Wax. See under Waxes
safrol & eugenol. Derived by distg the wood of
the Cinamonum camphora and separating the oiI
Candle, in Pyrotechnics, is an item(usually in
from solid camphor. Used as substitute for
the shape of a candle) which by its progressive
turpentine oil in varnishes, cheap soaps, shoe
combustion produces smoke or light over a
polishes, etc
comparatively long time(Ref 2). The color
Re/s: l)Kirk & Othmer 2(1948), 811 2)CondChem -
produced on burning of Amer pyrotechnic candles
Dict(1961), 211 is usuaIIY green, red or yeIlow and the
Camphorylazide. See 3- Azido. d- camphor under candlepower varies betw 5 & 25 thousand. For
Camphor example, the candles used in Amer 250-target
-identification bomb are small flares, ca 1.56” in
a. Camphylamine { called 52.Amino-l.2.2-tri. diam and ca 11.62” long; the candlepower of its
methyl-5 -.5thyl -cyclopenten-(2) or ~- [ 2.2.3 red flare is 25000, the burning time varies from
-Trim ethyl-A 3-cyclopentenyl 1 -.iithylamin in 1 to 11 reins and the light is visible up to 40
Beil }, miles; the candlepower of yel flare is 12000, the
burning time 1 to 11 reins and visibility up to

‘i
H3C. C—C(CH9)2’
CH2 \
CH.CH2.CH2.NH2 ; mw
40 miles(Ref 1)
R efs: l) Anon, “Military
1981 (1951 );19-22
Pyrotechnics”, TM9-
2) Glossary of Ord (1959),54
153. 26; dextrorotatory form is a Iiq, d 0.8688 at
20°, bp 202-4° at 760mm or 111-12° at 25mm; no Candlepower is the luminous intensity in terms of
1.47284 at 17.8°, Q: 1530.6 kcal/mol, [a]. +3.83° a standard candle (a candle made of sperm wax,
at 20°. Can be prepd by reduction of a-cam- six to the pound, which bums 120grains of wax per
pholenonitrile with Na in alc(Ref 3 & 4) hr). It is equal to 1.11 Hefner units
a-Camphylamine forms several salts, some Re/: Hackh’s (1944), 163
of them are expl: a)P ercblorate, C , OH, ~N.HC104,
CO1 trysts, mp 215 °(dec); explodes at 255 °(Refs Candlepower of Pyrotechnics Items varies
1 & 5) b)Picrate, no formula given, mp 194° with
according to the items. FoIlowing are some
total decompn; sinters at 190 °(Refs 1 & 2) and examples: Flares aircraft, parachute 60 to 800
c).2, 4,6, Tn’nitro-m-cresy late,
thousands; Flare aircraft M76 up to 850 thousand;
Cl OH, ~N.2C7H5N307, N 15.3%, yel ndls(from w), Cartridge photoflash Ml 12 50million; Bomb
mp 183°; expl on heating to 391° in a small tube photoflash up to 800miHion; Candles 5 to 25
{Ref l,p [35] & Ref 6} rhousand; Signals aircraft 12 to 30 thousand;
Re/s: l)Beil 12, 40, (127) & [35] 2)H. Signals, ground 2 to 35 thousand, Drift signals
Goldschmidt & L.Schulhof, Ber 19, 711(1886) 3) and Markers, 0.650 & 0.800 thousand and
F, Tiemann, Ber 29, 3009(1896) 4)W.J.Pope & Distress signal 8 thousand
J. Read, JCS 102, 452(1913) 5)R.L.Datta & N.R Ref: Anon, q‘Military Pyrotechnics’7, TM
Chatterjee, JCS 115, 1009(1919) 6)R.L.Datta et 9=1981(1951), 16-30
al, JACS 45, 2432(1923)
Cane Sugar or Sucrose. See under Sugars
Canada Asbestos impure clv-ysotile, a hydra-
ted magnesium silicate 3Mg0, 2Si2H2 ,2H20 Cane Sugar Octanitrate or Sucrose Octanitrate.
Re/: Hackh’s (1944), 162 & 201 See Nitrosucrose under Sugars

Canada Balsam. A yel, turpentine- like liquid from Canister or Case-Shot. A special short-range an-
incisions in the bark of balsam fir, Abies balsam- tipersonnel projectile consisting of a sheet-metal,
 C 25

cylindrical body and small steel or lead balls en- MIL-C-14113 and MIL-C-21OO4 cover requirements
cased in a resinous matrix, but no explosive chge. for such canisters
When fired from a gun, the canister case disrupts R efs: I) Hayes (1938), 561 2)Anon “Ammunition
just after leaving the muzzle and the bails scatter Inspection Guide”, TM 9-1904(1944) 3)Ohart
in the reamer of a shotgun chge, giving effective
(1946), 7 &86 4)F.W. F. Gleason, Ar@d 31, 369
coverage of the area immediately in front of the (1947) 5)Anon “Artillery Ammunition”, TM 9..
gun. Much used in 1812 and 1861, it was revived 1901(1950) 190 6) B. Bachem, BritP 751183 (1956)
during WWI for use in smaIl tank and aircraft guns 7) Glossaryof Ord (1959), 54 8) ’’The Macmillan
and then was widely used during WWII against Everyman Encyclopedia”, NY, 3(1959), 139-40
personnel and to clear dense undergrowth in
jungle warfare(Ref 1,3,4 & 7). Accdg to Gen Cannel Coal. A variety of soft or bituminous coal,
J. F. C. Fuller the “caseshot” was invented ca sufficiently hard to be cut and polished, It is rich
1410 in volatile matter (40- 60%) and bums with a cIear,
In Ref 2 are described under ArtiIIery yel, “candle-like flame. Its d is 1.2-1.3 and hear
Ammunition Canister, Fixed, Ml, which was value ca 14000 BTU. It is found in England (Lan-
deveIoped for the M1916 Gun and Canister, cashire) and US (Cannelburg, Indiana & J ellico
Fixed M2 developed for tank weapons to district, Kentucky). Has been used as a substitute
discourage personnel from approaching the tank for candles, as fuel in fireplaces, in metallurgy
In some chemical shells there is encased an and for enriching gases obtained from other coal,
ogival or cylindrical canister contg a compn which Has also been used as a component of Cannel Ex-
when ignited, produces a white or colored smoke plosives (qv)
(Smoke Canister) (Ref 7). Colored Smoke Canisteq Re/s: I)Kirk & Othmer 4(1949), 89-90 & 97 2)
M2 is briefly described in Ref 5 EncyclBritannica 4(1952), 745 3)VanNostrand’ S,
Following US Specifications cover require- Scientific Encyclopedia(1958), 262
ments for various canisters
a)MIL- C- 3298( @nister, colored smoke, 155-’mm
shell, M2) Cannel Explosives (Poudre au cannel). Expl mixts
b)MIL- C- 3299( Canister, colored smoke, 155-mm of Amm perchlorate and cannel coal suitable for
shell, M3) mining$patented in 1900 by AIvisi (Refs 1 & 2).
c)MIL-C- 3297( Canister, colored smoke, 155-mm The compn used in AustraIia contained 5ps of Amm
shell, M4) perchlorate and lp of camel coal (from Scotland)
d)MIL - C -3367A [Canister, smoke, for chemical (Ref 2). The compn given in Ref 3 is: Amm
shell (base ejection). Components for], perchlorate 80 & cannel coal 20%
e)MIL - C- 3 l19A(Canister, smoke, HC, 105-mm R efs: l) Alvisi, BelgP 148189(1900) 2) Daniel
shell, Ml) (1902), 106 3)CondChemDict (1942), 288 (not found
f)MIL-C-.3l 20A(Canister, smoke, HC, 155-.mm in later editions)
shell, Ml)
g)MIL-C-3121A(Canister, smoke, HC, 155-mm Cannel lo(Ital). Cannon Primer
shell, M2)
i)MIL - C- 14583 (Canister, smoke, WP, 5-in proj, Cannello a frizione(ltaI). Friction Primer
M5)
j )MIL-,C- 14585 (Canister, smoke, WP, 6- in proj) Cannello a percussione(ltal). Percussion Primer
Bachem (Ref 6) patented a canister shell
which, he claims, projects as nearly as possible, Cannello elettrico(ltal). Electric Primer
v erti call y upwards and opens in the vicinity or at
the actual vertex of its trajectory, to discharge or Cannelure. See under BULLETS (B. Bullets, Metal
release a flying or floating body Jacketed)
The term canister is also applied to that
part of gas mask which contains a filter(such as Cannizzaro, Stanislao(1826-1910). An Italian
activated charcoal or some chemical) for the chemist, known for his work in org chemistry and
removal of poisonous gases from the air being application of Avogadro’s hypothesis to the
inhaled(Ref 7). US Specifications MIL-C-1OO81A, atomic theory. The so-called “Cannizzato
 C26

Reaction” involves the oxidation of one It has been claimed by some historians,
mo!.ecule of aldehyde to the salt of corresponding that the English used at the battle of Cr&cy,
acid with reduction of another molecule to France( 1346), th~ee light cannons. Marshall(Ref
alcohol-by the action of coned caustic soln in 6) thinks that this is improbable, but Sir Charles
presence of a catalyst: C)man suggested(cited in Ref 15), that the
2RCHO+KOH+RCOOK+ RCH20H cannons used at Cr6cy were probably
R efs: l)W.A.Tilden, JCS 101,1677- 93(1912 )( Can- ribauldequins, weapons invented ca 1.339. They
nizzaro Memorial Lecture) 2)Hackh’ s(1944), 163 consisted of several iron tubes clamped together
3)Hickinbottom( 1948), 189-91 4) Great Chemists to form a device resembling a multiperforated
( 1961), 663-74 cylinder. The tubes could be fired separately or
simultaneously. Real cannons were used by the
CANNON(Geschutz in Ger; Pi$ce d’artillerie or English at the siege of Calais(1346)
Bouche ~ ‘feu in Fr; Oroodiye in Rus; P iezzo All early cannons were smooth-bore,
d’artiglieria or Bocca da fuoco in Ital and muzzle-loaders which fired either stones or
Pieza de artiller[a in Span). The term “cannon” darts. The first mention of solid iron projectiles
usually includes gun, howitzer and motar, but in (shots) was made in 1391(Ref 15), but hollow
our opinion recoilless gun is also a cannon projs filled with BkPdr(to act as an explosive)
Accdg to Amer definition, cannon is a were not invented until the 16th century
piece of ordnance, fixed or rnobil~intended to fire (Holland)(Refs 1,p 27)
projectiles of greater caliber than 0.60 incb(Refs Although rifled and breech-loading weapons
11 & 16). Its Brit definition is: “a weapon of were invented ca 16th century, they did not come
greater caliber than 1 inch” (Ref 14, v 4,P 751) into use because their manuf was too complicated
The term cannon does not include mount, for the machinery and tools existing at that
but only barrel(tube), breech mechanism and firing period. The first successful rifled, breech
mechanism -loading cannon was produced ca 1850 independ-
Accdg to Amer definition, cannons, recoilless ently by Cavelli in Italy and by Wahrendorff in
guns, rocket launchers and guided missile Germany. At about the same period, Whitworth in
launchers are classified as “pieces of artillery” England developed a helical hexagonal-bore
or ‘(pieces of ordnance’‘(Ref 16) cannon. It was one of the weapons used during
iiist;ricd. It was mentioned under ~lack P o~der (gv)> the Amer Civil War(1861-5)(Re~ 16,pp 4-16) -
that accdg to Col Ilirxe(?ef 2), the cannon was For more detailed history of cannons see
invented ca 1313 by an unknown German monk. Ref 15a,pp 15-73
There is however some evidence that Moors used, The following may be considered the
in the middle of 13th century, weapons firing current types of cannons:
large stones and darts(sieges of Seville and I)Gun(also called Cannon)(Kanone in Ger; Canon
,
Niebla in Spain) (Refs 3 & 16). Gen Fuller(Ref or Canon ray~ in Fr; Pooshka or Oroodiye in Rus;
15) states that the earliest document that mentions Cannone in Ital and Cation in Span). It can be
a weapon resembling cannon, is the Arabic defined as: a cannon with a relatively long
manuscript of 1304. Another Arabic manuscript barrel, high chamber pressure, low angle of fire
written at the beginning of 14th century was and high muzzle velocity & range. The term
located before the Russian Revolution in the q‘gun” is also applied to all firearms and this is
Asiatic Museum of StPetersburg. One of the confusing
most interesting known ancient manuscripts Modem guns are breech-loading weapons
describing a cannon is now preserved in the which have rifled barrels 30-40 calibers(or more)
Library of Christ Church, Oxford University, in length, capable to withstand pressures from
England. The manuscript was written ca 1326 in within higher than those developed in howitzers
Latin. It contains an illustration and a brief or motars. They fire projectiles at very high
description of the cannon formerly called “pot de muzzle velocity and with flat trajectory. Their
fer” or “fire-pot” and now known as the “Christ mountings permit, usually, elevations of 20-30°,
Church Gun”. Accdg to some manuscripts, the but some modern guns can fire at higher
Republic of Venice possessed some cannons as elevations Ref 9,p 4 & Ref 1 l,p 2)( See also Ref
early as 1326(Ref 3) and that the Moors used 19,p loll)
cannons at the siege of Alicante(1331), Tarifa E Ievation of antiaircraft guns is ca 85°
(1340) and Algeciras(1342)(Refs 3 & 8a) and some seacoast guns ca 65°

.— ——-
 C 27

Modern US guns may be subdivided into: walls, etc, which could not be reached by direct
a) Field Guns - weapons mobile enough to fire from flat trajectory weapons such as guns
accompany infantry and armored units in rapid (Ref ll,p 2; Ref 16,p 12 & Ref 19,p 1097)
tactial movement. They may be either towed or Because of its relatively low muzzle
self-propelled(Ref 16~P 14). In Ref 9~P 173 are velocity, a howitzer is less accurate than a gun
listed US guns, calibers 20mm to 4.5-in used and for this reason not recommended for use
during WWII and in Ref 16,pp 15-17, are given against small targets, such as tanks or aircrafr.
illustrations of some currently used US field guns It possesses, however, the following advantages
b) Aircra/t Gurz.s(Aircraft Cannons) include guns over a gun: a)Its lighter and shorter barrel
mounted inside or outside airplanes and used for permits throwing a heavier projectile than a gun
air-to-air, air-to-ground or air-to-water operations. of equal wt b)Its proplnt chge is not as heavy
The presently used US AC gun is the 20mm and is more flexible, and c) The life of a
Automatic Gun, but in the past, 20mm, 37mm and howitzer is much longer than that of a gun of
75mm AC guns were used(Ref 16,PP 14 & 16) equal caliber
c) Arztiaircraft Guns are designed to fire on AH howitzers are breech-loading, rifled
enemy aircraft, but can be used against other cannons, with barrels 20-30 calibers in length.
targets such as tanks. In Ref 9,p 173 are listed In Ref 9,p 173 are listed US howitzers used
US guns used during WWII and in Ref 16,pp during WWII, while in Ref 12,pp 114ff are given
19-20 are given illustrations of presently used illustrations and some props. In Ref I,6,pp 15-16
40mm, 75mm, 90mm & 120mm guns are given illustrations of presently used 75mm,
Note: The guns used against tanks are called 105mm, 155mm and 8in howitzers and in Ref 9,p
Antitank Guns 4 are some data on 75mm howitzers in comparison
d) Tarzk Guns are installed in full-tracked with that on 75mm guns
completely armored vehicles to be used against The distinction betw howitzer and gun is
ground targets or other tanks. In Ref 9,P 173 are now less marked than it was before
listed US guns used during WWII and in Ref 16,PP III)Mortar(~M6rser in Ger;Mortier in Fr; Mortira in
19-20 are given illustrations of presently used Rus; Mortaio in ItaI and Mortero in Spanish). A
76mm, 90mm & 120mm guns mortar may be defined as: a cannon with a barrel
e) Rai[way and Seacoast Guns were used by the sborte< muzzle velocity lower, angle of fire
US Armed Forces as late as WWII, but are not higher and range shorter than those of howitzers
used now(FLef 20). A description of these guns The usual length of barrel is 10-20
was given by Hayes(Ref 7,PP 285-329) and in Ref calibers and angle of fire up to 85°. A mortar
9,P 173 are listed the guns used d~ing WWIIO In can reach objects behind the hills or otherwise
Ref 8,PP 86-90 are given illustrations of 8in hidden, easier than a howitzer(Ref ll,p 2; Ref
Seacoast, 8in Railway and 16in Seacoast guns. 16,p 12 & Ref 19,P 1472)
h Ref 18,PP 256-9 are listed Ger g~s of WWII Historical: Accdg to Greener(Ref 1,PP 17-18), mortars
f)Nuval Guns are installed in ships. No info is may be considered as derived from ‘ ‘Bombard’‘(qv), a
at our disposal on these US guns. In Ref 18,pp weapon developed in the 14th century. The
252-9 are listed some of the guns used by the mortar as it is understood now was claimed to be
Ger Navy during WWII invented in Germany ca 1435(Ref 17, v 2,p 295).
Note: Ohart(Ref 9,p 4) gives data on 37mm Although mortars have been used for centuries,
Field, Antiaircraft, and Antitank guns used during their usefulness was not fully appreciated until
WWII, while Barnes(Ref 12,pp 62ff) gives WWI when a highly mobile type, called “Stokes”
illustrations and short description of guns used (or “Stove”) Mortar was developed. The
during WWH by the US Armed Forces original caliber was 60mm dnd it served as a
II)Howitzer(Haubitze in Ger; obusier in Fr; prototype for other mortars, such as 81mm and
Gaubitsa in Rus; “Obice in Ital and Ob~s in 4 .2in(See also below under Trench Mortar)
Span). It is a weapon intermediate between gun Majority of presently used mortars are
and mortar and may be defined as: a cannon with a smooth-bore, muzzle-loading weapons, but there
length of bawel shorter, chamber pressure & are also some rifled-bore muzzle-loaders, some
muzzle velocity lower, range shorter and angle o/ smooth-bore breech-loaders and some rifled-bore
fire higher than those of guns breech-loaders. As examples of rifled-bore
Its high angle of fire(elevatim UP to 65°) muzzle-loaders may be cited the 4.2-in Chemical
permits reaching targets behind hills, buildings, Mortar and the 914cm(36in) Mortar, nicknamed
 I

C 28

‘tLittle David”. The latter weapon used a shell IV) Recoilless Gun, misnamed Recoiziess Ri/le
with pre-engraved band(Ref 12,PP 172-3). AS (Riickstossfreie Kanone in Get; Canon saris recul
examples of smooth-bore breech-loaders may be in Fr; Bezotk6tnaya Pooshka in Rus; Cannone
cited the 2-in Mortar of Brit design installed on senza rincuio in Ital and Ca?ion sin retroceso in
some US tanks used during WWII and the 75mm Span). It is a cannon which petmits the discharge of
Infantry Assault Mortar, M1923. As an example projectiles with no rearward movement(recoil) of
of rifled-bore breech-loaders may be cited the barrel or mount
12-irr Seacoast Mortar, Model 1890, which is now In these weapons, vents or orifices are
obsolete(Refs 20 & 21) located in the rear of the chamber to carry off
Essentially, a modern smooth-bore, part of proplnt gases. These orifices are
muzzle-loading mortar consists of a tube closed openings that pass thru the breechlock, thus
at one end with a base cap contg a firing pin. providing an access from the chamber to the
Muzzle-loaded rounds must be complete as a atmosphere behind the barrel. The inside of the
unit(shell with a proplnt, igniter and primer chamber is considerably larger than the
attached to the tail end) so that when they are cartridge case which is perforated and lined with
dropped tail down into the mortar, impact with heavy moisture proof paper. These perforations
the firing pin is all that is needed to set off the allow escape of gas to the sides of the chamber
propelling chge. Smooth-bore shells must have and then to the rear of the barrel thru the
fins to stablize them in flight since rotation is orifices. The projectiles are provided with
absent. Besides mortars equipped only for rotating bands cut to engage the rifled bore. An
‘ ‘drop fire”, there are others equipped with overcharge of proplnt is required to achieve the
(‘combination fire” mechanism, which permits same muzzle velocity as with conventional guns
firing either by drop or by means of a trigger or of the same caliber and wt of projectile(Ref ll,p
by lever & lanyard arrangement(Ref 9,PP 190-4; 139-41 and Ref 16,pp 14 & 167-8)
Ref ll,pp 2 & 130-7; Ref 16,pp 160-6 and Refs These weapons are very accurate and weigh
20 & 21) much less than conventional guns
Ohart(Ref 9,p 5) and Barnes(Ref 12,PP Illustrations of presently used US
168-74) give some data on US mort~s used during recoilless guns, 57mm, 75mm, 105mm & 106mm
WWII. In Ref 18,pp Ger 250ff are listed numerous are given in Ref 16,p 24. German recoilless guns
Ger mortars of WWII. The largest weapons were of WWII, calibers 2cm to l>cm, are listed in Ref
54cm “Karl” M6rser, 61cm “Thor” Morser and 18,pp 239-56
80(or 82)cm ‘f Gustav” Geschiitz Note: We are including here also rocket and
lV)Trench Mortar(Grabenmorser in Ger; Mortier de guided missile launchers, because they are
tranch~e in Fr; Transheynaya Mortira in Rus; ~‘artillery weapons” and although they are not
Mortaio di trincea in Ital and Mortero de classified as “cannons”, their functions are
trinchera in Span)! Any mortar light enough to be identical. AH of them hurl missiles of larger
easily carried and installed in trenches, foxholes, caliber than 0.60in and for this reason cannot be
etc for firing at very high angles into enemy classified as small arms
trenches or against other targets which are closely V) Rocket Launcher or Rocket Projector
located from the weapon and hidden by some (Raketenwerfer, Raketenapparat or
obstacles may be called trench mortar(Ref 20 &21) Raketenwurfmaschine in Ger; Lance-f us6es in
Note: Trench mortar is not classified by some US Fr; Raketnitsa or Raketnyi Starter in Rus;
authorities as a cannon. We are listing it here Apparecchio lanciarazzi in Ital and Aparato para
because it is an artillery weapon and not a small tirar cohetes in Span). It may be defined as a
arm device for holding, aming and firing a rocket(Ref
Modern trench mortars were developed and ll,p 3 & Ref 16,P 169)
used during WWI. The most known of them were The projectiles(tockets) launched from
the “Stokes’’(6Omm) and the “Brand’’(45mm & these weapons are se If-propelling, traveling
60mm) mortars. A heavier mortar (81mm) was toward their targets by means of gases escaping
known as “Stokes-Brand’’( Ref 4,pp 129-31 & from combustion chambers within the rockets
Ref 5,pp 201-5) There are two types of rocket launchers:
Ohart(Ref 9,p 5) and Barnes(Ref 12)PP a)Open Tube Type Launcher consists of one or
160-7) give some data on 60mm & 81mm trench several(Multiple Launcher) smooth-bore tubes;
mortars used by the US Armed Forces during WWII each equipped at the base end with an electric
 C 29

firing mechanism. They may be mounted on Library of Congress) 14)EncyclBritannica 2

tanks, ships; vehicles or airplane s(See Ref 13,PP (1952), 464-7; 4(1952), 751 and 19(1952), 367D
182-91) 15)Gen J. F. C. Fuller, “A Military History of the
b)R ail Type Launcher consists of a launching Western World”, Funk & WagnaHs Co, NY, VOI 1
rail or beam together with elevating, traversing (1954), 464 & 469-70 15a)W.Y.Carman, “A
and equilibrating mechanisms. For example the History of Firearms”, StMartin’s Press, NY
7. 2in Multiple Rocket Launcher M17 contained 20 (1955) 16)Anon, ‘ ‘Principles of Artillery
sets of rails enclosed within armor plate, which Weapons”, TM 9-3305-1 (1956), 4-8 & 12-15 17)
protected the rockets from small-arms fire(Ref 12, Collier’s Encycl 2(1957), 295 18)B.T.Federoff
pp 192-3). The 8in Rocket Launcher T 53 was a et al, ‘ ‘Dictionary of Explosives, Ammunition
simple steel framework which also served as the and Weapons” (German Section), PATR 2510
packing and shipping container(Ref 12,PP 194-5) (1958),PP Ger 237-59 19)Merriam-Webster’s
Description of some Brit rocket launchers (1961), 327, 1011-12, 1097-8, 1472 & 1966 20)
maY be found in Ref 14, v 2,p 269B & v 193P A .B .Schilling, P icArsn; private communication
367D. A list of Ger WWH launchers is given in (1962) 21)H.H.Bullock, PicArsn; private
Ref 18,pp 249-59 communication(1962)
VI) Guided Missile Launcher is a device to hold
and aim a guided missile. There exist several Cannonites(Canonites in Fr). Fast-burning
types of launchers. Some are stationary(used smokeless proplnts patented ca 1889 by
for test purposes only), others are mobile and Chapman and manufd in England at the end of
capable of being moved to practically any place 19th century. The original compn consisted of:
that is accessible to conventional artillery NC(plus small amt of graphite) 86.0, K nitrate
pieces. In Ref 16,pp 173-4 are given illustrations 6.9, resin 6.2 & 0,9%(Ref 1). In Refs 2 and 3 the
of NIKE and CORPOR.AL launchers used by the compn of a 30-grain type shotgun Cannonite is
US Armed Fore es given as follows: NC 86,4, Ba nitrate 5.7,
vaseline 2.9, Iampblack 1.3, K ferricyanide 2,4 &
More info on this subject may be obtained volatile matter 1.3%
from the books on guided missiles Accdg to Ref 4, Cannonite was a smokeless
The section CANNON, etc was reviewed by proplnt manufd in the 1890’s by the War and
A. B.SchiIling of PicArsn, Dover, NJ Sporting Smokeless Powder Syndicate, Ltd. It
Refs: l)W,W.Greener, “The Gun and Its consisted of : NC(mostly insol in eth-ale) 86%,
Development”, Cassell, Petter & Co, London some Ba nitrate and smalI quantities of K nitrate,
(1881), 17-18 & 27 2)C01 H. W. L. Hime, “The charcoal, Iampblack, vaseline, rosin, stearine,
Origin Of Artillery”, Longmans, Green & Co, NY DNB, TNT, K ferrocyanide & graphite. For
(1915), 120 & 127 3)Marshall 1(1917), 18-19 rifles the ptoplnt was fully colloided. The
4)Anon, “History of Trench Warfare Mat~riel”, compn given in Ref 5 is nitrocotton 86, Ba
Army Ordnance Pamphlet(1920)( available at nitrate 6, K ferrocyanide 2, lampblack 1&
P icArsn Museum) 5)J .H.Wallace, ‘ ‘The Field vaselin 3%
Artillery Journal, March-April 1932,pp 201-5 Re/.s: l)Daniel(1902), 106-8 2)W.Macnab & A.E.
(available at PicArsn Museum) 6)Marshall 3 Leighton, JSCI 23, 299(1904) 3)Marshall 1(1917),
(1932), 1-2 7)Hayes(1938), 153-85 7a)J.H. 327 4)Marsha11, Dict(192@, 18 5)CondChemDict
1v euman, “The Tools of War”, Doubleday, Doran & (1942), 288(not found in later editions)
C0,NY(1943) 66-175 8) Anon, ‘ ‘Modern Ordnance
Mat~riel”, Raritan Arsenal, Feb 18, 1943 8a) CANNON PROPELLANT or CANNON POWDER
P~rez Ara(1945), 139 9)Ohart(1946) 35 & 173 (Geschiitztreibmittel or Kanonenpulver in Ger;
10) F. W. F. Gieason, .ArdOrd 32, 48( 1947) ll)Anon, Poudre pour canon in Fr; Artilleriiskii Porokh in
“Fundamentals of Artillery Weapons” TM Rus; Polvere per cannone in Ital and P61vora para
~-2305(1947), 1-5 12) G. M. Barnes, “Weapons” caiion in Span), US cannon propellants may be
>f World War II”, VanNostrand, NY(1947), 122-3, defined as compositions designed to propel heavy
125-6, 128-31, 134-5, 140-2, 144-56 & 159-74 projectiles from artillery weapons called cannons
L3)A.D ,Blinov, “Kurs Artillerii”, Voyenizdat, at high velocities without causing damage to
Aoscow, Vols 1-12( 1948 -1952 )(available in either weapon or projectile
Historical Black Powder(qv) was used
exclusively until about 1860’s. Then, attempts

I
 c 30

were made to replace it with smokeless proplnts proplnts used in small arms in order to prevent the
made from incompletely colloided NC. These development of excessive pressure in the barrel,
proplnts were” too fast-burning for cannons(see which might cause its rupture d)Its heat of expln
below under Single-Base Propellants). Attempts and flame temp should not be too high in order to avoid
were made to use proplnts containing picrate, excessive erosion of the barrel e)It should not
such as powder of D6signole(qv) manufd in produce bright muzzle flash and smoke visible
France ca 1869. In order to decrease the rate of from a great distance f)It should burn uniformerly
burning of BkPdr, the completely charred producing the desired ballistic effect g)It should
carbonaceous material(charcoal) was replaced by not burn depressively, but progressively except in
incompletely charred material. The compn contg some small caliber cannons, where neutral
this material, together with K nitrate and sulfur, burning proplnts may be used and h)It should be
was known as Brown-, Chocolate- or Cocoa non-hydroscopic and stable thruout long storage
Powder. It was used in Europe and US betw under a wide variety of atmospheric conditions
1880 and 1900 as proplnt for larger caliber Grains of cannon proplnts employed in the
cannons. With the development of smokeless US are usually either small single-perforated
proplnts based on fully gelatinized NC or on cylinders(used mostly in 20mm guns and in some
NC-NG, all the above cannon pdrs became howitzers) or large cylinders with seven equally
obsolete(See also below under Single Base and spaced perforations(used in larger caliber
Double Base Proplnts) cannons). Some rosette-shaped proplnts were
The present use of BkPdr as a proplnt is used in mortars. Other shapes of gtains, such as
restricted to some shotguns or older types of coral, flake, strip, tube, cube, tri-perforated
rifles. It has also been used as an igniter of cylinder, star-perforated cylinder and cruciform
cannon proplnts but, as it produces some smoke, grains have been used in European countries,
there is a tendency to replace BkPdr by fibrous such as Germany(See Figs 1 & 2 and Ref 10,p
NC. Other current uses of BkPdr are discussed Ger 146). Shapes of typical rocket proplnts
under Black Powder (Fig 3) are given here for comparison
A good cannon proplnt should possess the
following properties: a)It should be non-corrosive
to cartridges or projs b)Its gases of expln should
not be erosive to the barrel of a cannon c)Its
burning rate should be slower than that of

MULT 1.
SINGLE. TR!.
D
. w“’-
Ccw PERFORATED PERFORATE PERFORATED eoxr

Fig 2

[~HHn~
$:

0255075, co 02550 751W o 15 50 75 lCQ 02550751 W0255C

PIRCENT Cf GRA,N CCNMJMID

?00
Fig 1

t.! ,3

,,& ,,N
@ ‘B’ Figs
 C31

The size, shape, number of perforations and large caliber. Some countries such as Germany
cross section of proplnt grains are chosen ~or each (see Ref 10,P Ger 146) and GtBritain(See
type of weapon so as to give the optimum burning Cordite) have used depressive burning proplnts
rate for that weapon. The size of the grain m their cannons
determines to a great extent the burning rate of US Specification requirements for sizes of
the proplnt: the larger the grain, the slower the grains used in cannon proplnts are briefly
rate of burning. As a general rule, the greater discussed under Camon Propellants, Analytical
the caliber of a weapon, the larger the proplnt Procedures
grain should be. In case of a multiperforated A table of physical forms and dimensions
grain, the size usually refers to the average web of typical US propellant grains is given at the
thickness which is the mean of its outer web end of this volume (Table IX)
thickrzess(min dist betw the outer periphery of As grains of cannon proplnts are rather
the grain and the wall of an outer perforation) large, it is difficult to remove from them
and its inner web thickness(min dist betw the completely(by drying) the volatile liquids(such as
wall of central perforation and a wall of an outer solvents and water) used .in their manuf. This
perforation)(See Fig 4) means that these proplnts contain appreciable
amts of “residual volatiles” and this must be
rwEe T f- SLIVSRS
~
taken into consideration when considering the
ballistic props and burning rates of such proplnts
00 (Ref 9,P 225)
The relative sizes showing side and end
0 ~o
views of typical US cannon proplnts are given in
@ Fig 5

Diameter of perforations in a grain also

influence its burning characteristics.
three or seven perforations
purpose of obtaining “progressive
The use of
in a grain is for the
burning
49
m-w
44
40-MM 57-MM
propellants”, ie proplnts in which the surface
area of grains increases during burning until the
point is reached when nothing is left but
triangular pieces, known as “silvers”. These
pieces of proplnt burn depressively and usually
in the bore of a weapon; but if the barrel of a
weapon is relatively short, some incompletely 74-MM %-MM 105-MM
burnt slivers might be expelled from the muzzle,
The rosette or Walsh grain, with a scalloped
outer periphery reduces the amt of slivers Fig 5
produced by a multiperforated grain and therefore
reduces(or even eliminates) the amt of unburnt
proplnts ejected from weapons. Rosette grains
were used in some US seacoast mortars(Ref 9,p
224)(See Figs 1,2 & 4)
Single-perforated grains burn in two
directions and the initial diam of perforations
155-MM S-lNCH
cm be so chosen that the total burning surface
changes but little during burning. Such a grain Accdg to compositions, cannon smokeless
is said to have ‘%eutral” characteristics. As the proplnts may be subdivided into single-base- ,
surface area of grains, such as flakes, strips, double-base- and triple-base-proplnts. The last
cords, cubes or balls decreases continuously two proplnts are sometimes called “compound~’
luring burning until the grains are completely proplnts. The so-called “composite” proplnts,
consumed, such grains are said to bum used in JATOS and rockets, are described under
“depressively”. These grains are not very Composite Propellants
suitable for use in cannons, especially those of I)Single-Base Cannon Propellants(Nitrocellulose
 c 32

Cannon Powders). Single-base proplnts intended approved for service in the US Navy and the
for use in cannons are solid compns contg as a manuf started on a small scale ca 1897 for the
major ingredient NC, fully gelatinized by a Navy and ca 1899 for the US Army(Ref 8a). It
volatile solvent(such as eth-ale) with or T@ DNT, was used during Spanish-American War(1898)
TNT or MNN which act as auxiliary gelatinizes Accdg to Davis(Ref 6,p 297), the Naval
and as flash reducers. As minor ingredients, Powder Factory(now called US Naval Propellant
these proplnts contain a stabilizer(such as Plant), Indian Head, Md, was built in 1900, for
DPhA) with or @ a flash reducer(such as K manuf of this “P yro” proplnt, and manuf of
sulfate) this proplnt at Picatinny Arsenal, Dover, NJ was
Historical. NC proplnts prepd before 1884, such started in 1907
as of Schultze(invented in Germany ca 1865), of The original US “Pyre” proplnt contained
Volkmann(invented in Austria ca 1871) and the no stabilizer until ca 1909 when 0.5% of DPhA
EC (invented in England ca 1882) contained was incorporated. At the same time glazing of
partially colloided NC(Ref 2,pp 4-5). They grains with graphite was introduced. The amt of
burned so fast that when tried in cannons, the DPhA was increased during WWI to 1%. As
powder chambers were either damaged or burst ‘ ‘Pyre” proplnts were hydroscopic, a low
open -hydroscopic proplnt, known as NH(Nonhygroscopic)
It has been generally understood, that P. was developed ca 1930. Its compn was:
Vieille. of France, was the sole inventor of the NC(13.15% N) 87, DNT 10 & DBuPh 3%. Ar
modem colloidal single-base proplnt. This about the same time, the proplnt called FNH
proplnt, known as Poudre B, was invented in (Flashless-Nonhygroscopic) was developed. Its
1884 [See B(Poudre) in Vol 2 of Encyclopedia] . compn was: NC(12.6% N) 74, NC(13.25% N ), 20,
Accdg to Brunswig(Ref 2,pp 6-7), M.von DNT 5 & DPhA 1%. Designations NH and FNH
Duttenhofer of Germany, invented a similar are not used any more, being replaced by letters
proplnt a few months earlier than Vieille. The M or T followed by numbers 1,2,3 etc(See Tables
von Duttenhofer’s proplnt was approved by V, VI&VII). M means a proplnt adopted for service
German War Dept and later became known as and T, one in the experimental stage
RCP(Rottweiler Cellulose Pulver), because it Current US Single-Base Cannon Propellants, In
was manufd at the Rottweil Plant of Dynamit Table V there are listed only three proplnts
A-G. While the compns of Fr and Ger proplnts (MIAI, M3D & M31) which are based on
were kept secret, some other countries worked ‘tPyrocellulose” (NC with 12.6zN), because
on the same subject. In about 1891, C.E. the majority of proplnts are now based on
Monroe(US) succeeded in preparing a single-base ‘ ‘Blend” (NC 13.15 -13.25%N), which is prepd by
colloidal proplnt, called [rzdurite, while D.I. mixing “P yro” (12.6zN) with Guncotton
Mendeleev(Russia) prepd a proplnt called (13.4-13 .45%N). The 1st component is sol in
Pyrocollodion. The latter proplnt was based on 2 :1-eth-ale, while the 2nd is not. Cannon
NC (N= 13.44%) which contained a sufficient amr proplnts Ml, M6, M14 and recoilless gun
of oxygen for complete combustion to CO & H20. proplnt M1O are based on NC with 13.25%N and
This proplnt was adopted by the Russian Armed so are small arms proplnts IMR (Improved
Forces and was used for many years Military Rifle) and M12 (listed here for comparison
ils Indurite was found to be not very with cannon proplnts)
suitable for use in cannons, the US Navy In above proplnts DNT acts as a gelatinizing
decided to investigate the Russian proplnt. & waterproofrng agent and, being a weak expl, it
This was done by Lt B. Bernadou, while he was contributes to ballistic characteristics. It has
stationed in StPetersburg as US Naval Attach<. also a slight flash-reducing action .
B found that although Mendeleev’s proplnt was Accdg to Dr Walter (Ref 13), when DNT
satisfactory for use in cannons, better ballistic (or TNT) is incorporated, the resulting compn
characteristics could be obtained with NC of can be easily extruded or rolled to produce
slightly higher N content, such as ca 12.6% N.He grains which are, at RT, hard but not brittle
prepd ca 1895 the proplnt by colliding NC of When DNT is used for coating the grains
N 12.6% with eth-alc and called it ‘tpyrocellulose (as in IMR & M12 proplnts), not only the proplnt
Powder”. h was also called c‘Pyrocollodion” or becomes waterproof but also the initial rate of
‘ ‘Pyre” Powder, but now the word “powder” is burning proceeds at relatively low and uniform
replaced by C‘propellant”. This proplnt was rat e

.—. —.. .——.— .—

1
 c 33

DBuPh, DEtPh & triacetin are gelatinizing, except that a mixt of ethanol & acetone(in lieu of
waterproofing and flash-reducing agents. K ethanol-ether)is used as the solvent and the
sulfate, cryolite & tin are flash-reducers, while . solvent recovery procedure is omitted because of
tin also acts as a decoppering agent. DPhA and the hazard involved in treating material contg NG
EtCentr are stabilizers and Pb carbonate an and b)Nonsolvent of Solventless Process used
antacid. GIazing of grains with graphite is done when NG and any other coHoiding agents
to prevent caking in storage, to facilitate blending constitute ca 40Y0 of the compn. In this process
and loading, to improve the burning characteristics the wet NC is mixed with NG and then with
and to prevent the formation of large static chges EtCentr. After removing the bulk of water by
during blending and loading centrifuging, the resulting paste is put in cotton
One of the single-base proplnts formerly bags which are placed in dryers operated by
developed at PicArsn for 90mm cannons, circulating hot air, After thorough blending the
contained DNEtB(dinitroethylbenzene) 10, remaining constituents of proplnt with partly
cellulose acetate 5, NC(13. 15%N) 84 & EtCentr dried paste, it is subjected to repeated rolling
1%. Here DNEtB acted as an expl gelatinize, between steel rolls heated by circulating steam
flash-reducer and waterproofing agent, while inside of them. These operations remove the rest
cellulose acetate was added as flash-reducer of w and complete colliding of NC. The
(PicArsn Specification PXS-1 197) thickness of the resulting sheet varies with the
Manuf of single-base proplnts in the US is . desired size of grains. This proplnt is called
described in Ref 5,pp 21-8, Ref 5a,pp 20-36 and *8Solventless” Propellant [Poudre SD(sans
Ref 6,pp 299-306 dissolvent) in Fr and POL (Pulver ohne
Foreign single-base proplnts are listed at L6sungsmittel in Ger]
the end of this section Properties of Double-Base Cannon Propellants.
II)Double-Base Cannon Propellants. This term is Double-base NC-NG proplnts are considered “hot”
applied in the US to proplnts contg NC and NG as proplnts, because their heats of expl and flame
major ingredients, while in foreign countries such temps are much higher than those of single-base
as Germany or Italy, the term is extended to proplnts (See Tables V, VI& VII). This means that
proplnts based on NC and DEGDN(or TEGDN or muzzIe-flash and gun barrel erosion are higher
Metriol Trinitrate). As minor ingredients with double-base than with single-base proplnts.
double-base proplnts may contain stabilizers(such For example, tests conducted in Germany,
as EtCentr), flash reducers(such as K sulfate, sometime before WWII, showed that if an average,
ctyolite or triacetin) and other ingredients(such barrel life when using single-base proplnts is ca
as Ba nitrate Y K nitrate, K perchlorate Y carbon 3500 firings, it is reduced to ca 1700 firings
black and graphite) when using double-base proplnts
Historical. The first successful double-base In order to make the US NC-NG proplnts
proplnt, called “Ballistite” (qv), was invented ~~cooler” and consequently less erosive,
in 1888 by A.Nobel of Sweden(Ref 6,p 292). As NGu was incorporated. The resulting compns
this proplnt, as well as the double-base proplnt are, strictly speaking triple-base proplnts(See
cCordite’’, developed ca 1889 in Abel’s Table V, Proplnts M15, M17, T20, T29, M30 &
laboratory, England, had very high flame temps, M31)
it was extremely erosive to gun barrels. When
amts of NG in these proplnts were considerably SEE TABLES V-VI-VII NEXT PAGES
reduced(co lower their flame temps), proplnts Accdg to info supplied by Costa & Trask of
suitable for small caliber cannons were obtained PicArsn, the thermodynamic props of cannon
and used during WWI & WWII in Italy, GtBritain proplnts listed in Tables V, VI & VII were detd
and Germany. In the US no double-base proplnts as follows:
were used in guns prior to WWII, but some were A)Isochoric Flame Temperature, Tv, in ‘K, from
used in mortar and small arms ammo. During and
after WWII some double-base proplnts have been the formula TV=2500+ ~, where E is relative ener-
standardized in US for use in small caliber guns Cv
and also in rockets gy in cal/g and Cv mean heat capacity at const
Manufacture of Double-Base Propellants. The vol in caI/g/deg. E is the sum of values calcd for
following methods are used: a)Solvent Process each org component from the formula
-similar to that used for single-base proplnts, E.(-E)-132~~~Cwj40026H- 6724N+51 .81$0,
 Table V

US Gun and Howitzer Propellants Composition (Including Residual Volatiles) and Some Characteristics

Propellant Ml Ml Al M2 My M6 Ml 4 Mi 5 M17 T20 T28EI T29 M 30 M 31

Specification MIL-P MIL-P MIL-P MIL-P MIL-P MIL-P MIL-P MrL2
-309A -668A
Nitrocellulose(NC) 85.00 84.50 22.00 20.00
(% Nitrogen in NC) (13.15) (I2.6o) (13.15) \l;.l;)
Nitroglycerin — 21.50
Barium Nitrate — 1.40 1.40 – —
Potaasium Nitrate 0.75 0.75 – —
Lead Carbonate — r.oo*
Nitroguanidine( NGu) — 74.70 ?4.70 60.00 ;0.70 i7.70 54.70
Dinitrotoluene( DNT) :0.00 :0.00 — 10.00 ;00 —
Dibutylphthalate( DBuPh) 5.00 4.50 3.00 2.00 — — ;.00 4.50
Diphenyl amine(DPhA) 1.00 * 1.00 — 1.00” 1.00’ — — — 1“.50
2-Nitrodiphenyl mnine(NDPlrA) _ — 1.50
Ethyl Centrrdite( EtCentr) - ;,60*** CI.@3*** : :00 i. 50 200 ;00 <50 1.s0 -,
Grabhite — 0.30 0.30 – 0.10”” 0.90 ;yo* *
Crjoli te
K75 zoo z 30 :30
i 30
0.30
0.30
;.65
Y3z” 0.30
Ethyl Alcohol(Residusl) ;90 1.00 0.30 ;30 0:30 0.30 0.30
Water(Residual) 0.50 0.60 0.70 0.70 0.50 0.25 0.00 0.00 0.00 0.25 0.00 0.00 0.00
2225 3319 3245 2570 2710 2594 y:; 2388 3132 3222 2599
287 360 355 317 327 336 314 ~~ 371 ;3$
Unoxidized Carkn, % “ 8.6 10.0 0 0 5 9:5 3.9 11.6
Combustibles, % 65.3 73.8 47.2 47.4 :;!4 58.9 51.0 ;~. ;~$ 5k2 ~i?7 ; ;io 4;.8
Heat of Explosion, c~/g, Q 637 1080 1047 758 809 796 977 1034 807
Gas VOlume,rnO}es/g,n o~jit; 3 : .;604:30 0-.03900 0.3935 0.04432 0.04338 0.04645 0.04336 @.04794 0.04164 0.04133 0.04308 0:0462(
1.2238 L&58 >.2:43 ;i;$96 $#J7 }42$02 : .2;91 1.2384 l#~;9 1.2385 1.2527
;s::s:: $ek%?rr;;%$, Tp 1;19 1763 2712 2529 2455 2057
Specific Gravitv,g/cc 1.57 1.56 1.65 1.65 1.58 1,61 1.66 1.67 1..66 1.61 1.66 1.66 1.64
30.57 31.22 27.91 27.52 29.92 29.54 31.17 29.50 30.41 28.74 28.47 29.26 30.87
Covolume,in 3/lb, ~i 0.00576 0.0036(
Burning Rate Char- 0.002143 — 0.002432 - 0.002989 0.004108 0.006956
acteri{tic of Equation
~= BPn at 210(s ee Note)
0.710 – 0.755 – 0.702 – 0.675 0.632 – - 0.652 0.644
Pressure ExpO-
nent, n 0.2 0.2 - - 0.2 0.2
(LI – 0.1 - 0.2 –
~;%g ‘ensity’

Note: r= BPn gives rate of burning r(in/see) as function of pressure P(psi)

*Added * *Glaze added * * *DiPhenylamine was used before March 29} 1946
 c 35

Table VI
US Mortar and Small Arms Propellants
Composition (Including Residual Volatiles) and Some Characteristics
Mortar Smal I Arms

Propellant J!!:-P J !!J-P M??-P J L“{-b J“~~P FM:-%;*

Specification -659 -381 -20306 -733 -528 *26A

Nitrocellulose(NC) s4.60 52.15 57.75 100.00 97.70 80.00

(% Nitrogen in NC) (13.15) (13.25) (13.25) (13.15) (13.15) ;:36;5)
Nitroglycerin 35.50 43.00 40.0-0 – –
Potassium Nitrate 1.25 1.50 - - –“
Potassium Perchlorate ;.80
.. . - - – - _
Dinitrotoluene( DNT) — 8.00”” 8.00**
Dibutylphthalate( DBuPh) ;.00
Dietbyphrhalate( DEtPh) ;.00 z ~ –
Porai;ium Sulfate — 1.00’ ;.75
Tin — 0.75
Diphenylamine(DPhA) 0<70’ 0.80 ;.00
Ethyl Centrrdite(EtCentr) ;.90 0.60 ;.75 -
Carbon BI ack 1.20
Ethyl Alcohol(Residud) 0.80 z 40 ;.50 C50 :.50 ;. 50
Water(Residual) 0.00 0.00 0.00 1.00 1.00 0.00
Isochoric Flame TeIIp, *K, TV 3734 ;:;5 3799 2835 2823 2577
Force, ft-lbs/lb x 10 , F 368 382 331 331 319
Unoxidized Carbon, % 0 o (1 2.7 3.0 6.8
H eat of Explosion, cal/g, Q 1255 1244 i295 868 863 772
Gas Voiume, moles/g, n 0.03543 ;.;;;;1 ;.;;;;8 0.0419 0,042110.04457
Ratio of Speclflc Heat% 1.2100 1.2413 1.2421 1.2523
3085 3i42 3i39 2284 2273 2058
::::::::L,T/F:’ z ‘p 26.63 25,95 28.91 29.02 ~.;4
Combustibles? % ‘ 1 3;.4 37.2 32.8 59.2 59.2
SpecAc Gravity, g/cc 1.69 1.62 1.6o 1.62 1,62 1.62
* Added **Coating added ***Ball propellant iVote; Small Arms Propellants are included for comparison

Table Vll
US RecoilIess Rifle Propellants
Composition (Including Volatile Solvents) and Some Characteristics
Propellant M1O 12S MM T31 T32 T33
Specification

Nirrocelltdose(NC) 98.00 73.25 67.25 30.00&25.00 30.95&25.80 21.30&35.45

(~ Nitrogen in NC) (13.15) $;3i.15) (13.15) (132b#3)&(13.15) (12.20)&(13.35) ~52b~O)&(13.35
Nitmglycerin(NG) 2s.00 35.00
Barium Nitrate 0.;5 0.75 — —
Potassium Nitrate 0.70 0J70 —
Potassium Sulfate 1.00 — —
Diphenylmnine(DPhA) 1.00
E~hyl Centrali te(EtCent) — ;.00 ;00 ;.00 7.95 ?.95
Graphite O.1O** 0.30 0.30
Carbon BIack :.; :$ 0.30 0.30
E tb yl Alcohol(Residusl) ;.50 ;. 20 ;.20 0.50 0.50
Water(Residual) 0.50 0.30 0,30 0:00 0.00 0.00
po;;:;;,;:~;
.
:;oq:;L Tv ;;;0 3071 3081
356
3674
387
3100
366
353
Unoxidized Carbon, % 4 1.8 2.2 0 3.0
Combustibles, % ;J.; 56.1 57.3 38.9 58.8
Heat of Explosion, cal/g, Q 962 966 1222 957
Gas Vohme, rnfles/g, n 0.04068 0.04133 0.04157 0.03788’ 0.04246
Ratio of 5P eclflc Heat~ 1.2373 L2383 1.2174 1.2419
~;;o~:~l~k~e~, ~ Tp $;::2 2482 2488 3018 2496
27.76 ;82$6 ;8~;7 ;6;~ 29.15
Specific kravlry, ‘u~c 1.67 1.62

*Added * *Gla=e Added

 C 36

where (-E) is heat of combustion in cal/mole) and The idea of incorporating NGu in prophtts,
Cv is calcd from the formula seems to have originated in Germany, where General
Cv. u+~oq.wt H+3.3.84N+5.
- 193Q . U. Gallwitz developed, before WWII, the triple- base
proplnt called Gudolprdver (See Ref 10,p Ger 143).
If Tv is found to be over 30000K a better Prior to this the Germans developed rather “cool”
approximation may be obtained from the formula proplnts by replacing NG with DEGDN or TEGDN,
Tv= 3000+6046{ -( Cv+O.O 1185)+[(Cv+o.01 185)2+ and the Italians developed proplnts contg Metroil
3.308( 10-4)( E-500CV)]’12] Trinitrate in lieu of NG. In France, H. Muraour
B) Force, F, in ft - lbs/lbx103, was obtained from proposed, befor WWII, a proplnt conrg DEGDN 22,
the formula F=nRTv, where n is gas volume in NC(1 1.9%N) 67, EtCentr 9 & K sulfate 2%
moles/’g and R is gas constant= 1.9885 cal/degree In order to make the temp of expln still
C)Unoxidized Carbon. This value is the calcd amt lower, mono- and dinitronaphthalenes were
of carbonaceous smoke produced by proplnt in bal- incorporated in some Ger NC-DEGDN proplnts.
listic tests. Assumptions made to simplify calcns The resulting compns were not as “cool” as
are as follows: later developed proplnts contg NGu(See under
l)Proplnt gasedconsist only of C02, CO, H20, H2& Triple-Base Propellants)
N2 2)N2 gas is nor involved in smoke 3)A11 C02& US Double–Bus e Cannon Propehnts. In Tables
H2 formed are considered as equiv amts of addnl V, VI & VII are given compns and some props of
CO & H20, without affecting fuel-oxygen balance presently used proplnts. Proplnts M2, M5, M7, M8 &
4)AIl H2 is oxidized to H20, any remaining 02 M9 are C‘standard”, whereas proplnts T31, T32 &
oxidizes sOmeC to CO, and unoxidized C represents T33 are experimental. Proplnts contg NC, NG &
carbonaceous smoke NGu are listed here under Triple-Base Propellants
The excess (or deficiency) of oxygen in an (See below)
org compd or its “oxygen balance”, in percentage In US NC-NG proplnts, NG is used as an
of 02 reqd for complete conversion of C to CO and expl plasticizer for NC; EtCentr as stabilizer;
H2 to H20, can be calcd from its empirical formula carbon black as burning regulator; K sulfate and
as follows: cryoIite as flash reducers; Ba & K nitrate, as well
as K perclorate(See Note below) being oxidizers,
OB to CO & Hz O= ~0-~5~-~–1~~
improve ignitability of proplnts(Ba salt also
The “unoxidized carbon” value is obtd by increases the bulk density of proplnts); 2-nitro
multiplying the oxygen baIance by mw of C over DPhA was used as a stabilizer in lieu of DPhA
the mw of O, or by 12/16, If several org which, being alkaline, was not suitable for
substances are present, the total value is equal proplnts contg NG(Ref 13). Graphite was used
to the algebraic sum of individual val ues(See also for the same purpose as in Single-Base Cannon
Available Oxygen, Vol I,p A515-L) Propellants
D)Heat of Explosion, Q, in cal/g was calcd for Note: K perchlorate used in mortar proplnt M7
each org component from the formula: (See Table VI), would be unsuitable for use in
proplnts for weapons with long rifled barrels(such
Q= ~<~;#C+O.5H-0) , as guns). This is because KC104 forms, on
decompn, KC1 which is very erosive at high temps
where (-E) is heat of combustion in cal/mole
(Ref 13)
E)Gas Volume, n, in moles/g, was calcd for each One of the older US mortar proplnts contained
org component from rhe formula,
vaseline(petroleum jelIy) which presumably acted
‘= W$WK as a stabilizer and flash-reducer. The compn of
this proplnt was: NC(13.15%N) 54, NG 43 &
F )Ratio of Specific Heats, y, was calcd from the
vaseline 3%, with 0.57. DPhA added(US Spec
formula
50-12-4A). Another older US cannon. proplnt
Y=l+l.987& contained TNT and hydtocellulose. Its compn
v
was: NC(12.6%N) 49, NG 20, TNT 20 &
G) Isobaric Flame Temperature, TP, in ‘K, was hydrocelIulose 10%. Here TNT was added for
calcd from the formuIa TP=Tv\y the same purpose as DNT(See under Single-Base
H)Covolume, ~i, in in3/lb, was calcd for each Cannon Propellants). Hydrocellulose was used
component from the formula: as flash-reducer. Its 1‘cooling” effect is due to
q i=O. ~-#$&0B+2d~X27.7 development of large amts of gaseous products,
 c 37

which are sufficiently cool to eliminate ]aparz. Used nearly exclusively single-base
muzzle-flash, but sometimes cause formation proplnts, such as: a)NC(13.l%N) 93.3, DNT 5.5,
of .wnoke DPhA 1.0 & graphite 0.2% b)NC(l 3.O%N) 91.0,
Foreign double-base proplnts are described DNT 8.0, DPhA 0.6 & graphite 0.4% c)NC( 12.5%N)
at the end of this section 92.5, DNT 5.0, tin 2.0 & DPhA 0.5% and d)
III)Triple-Base Cannon Propellants. These NC(12.9%N) 93.1, DNT 5.0, tin 2.0, asym-DPhU
proplnts contain as major ingredients NC 1.5 & graphite 0.4%(Ref 9,p 266), Japanese NC
together with an “explosive oil’ ‘(such as NG, was usually prepd by nitrating woodpulp. Compn
DEGDN, TEGDN or Metriol Trinitrate) and of one of their double-base propInts was: NC
nitroguanidine [NGu>, being used as a finely (11.8%N) 72.0, NG 19.5, K nitrate 2.5 &
divided pdr dispersed thruout the NC -explosive asym-DPhU 6. O%(Ref 9,p 266)
oil colloid, contributes to ballistic potential Mexico. Used single-base proplnts manufd at the
and also acts as a cooling agent. It developes, F~brica National de P61voras, Santa F~, DF
on explosive decompn, large amts of gases which (Ref 8c)
are cooler than the gases produced by NC and Russia. Used both single- and double-base
explosive oils. As minor ingredients of proplnts, such as: a)NC(12.6 to 12.8%N) 98.7 to
triple-base proplnts, stabilizers (such as EtCentr) 99.3 & DPhA 1.3 to 0.7% and b)NC(13.l%N)
and addnl flash reducers(such as K sulfate) are 64.4, NG 20.8, DNT 3.9, vaseline 2.6, EtCentr
used 1.3, asym-DPhU 6.7 & graphite 0.3%(Ref 9,p 266).
US triple-base proplnts are based on NC, Compns of several Russian cannon proplnts are
NG and NGu. They are designated as Ml 5, given in conf Ref 9a(8 unclassified refs)
M17, T20, T29, T34 & T36(See Table V) Spain. Used single-base propInts manufd in
Foreign Cannon propellants. The info given several Govt and private plants, such as
below mostly concerns proplnts used at the time Granada, Murcia & Gald6cano(Ref 8)
of ca WWII: Sweden. Used both singIe-base and double-base
Argentina. Used both single- and double-base proplnts. History of development of proplnts in
proplnts. See Vol 1 of this Encyclopedia,p Sweden is described in Ref 10a, where are also
A478 given analytical procedures, but no compns of
B elgr’urn. See VOI 2, under Belgian Explosives proplnts. Under “Bofors Propellants” in Vol 2
and Propellants of this Encyclopedia are given formulations of
France. See Vol 2, under B(Poudre) some older Swedish proplnts, as well as of the
Germany. Used single-, double- and triple-base newer proplnt h4K7(Nobelkrut 7) of AB Bofors,
proplnts. See Ref 9,pp 263-4 and Ref 10,PP Ger NobeIkrut
141-6. Gudolpulver is described in Ref 10,p Ger Switzerland. Used both single- and double-base
81 proplnts manufd at the Govt plant at Wimmis
GrBritain. Used nearly exclusively double-base (Bern). The compns of current proplrrts have
proplnts called Cordites. Compn of a single-base not been revealed(Ref 8b)
proplnt is given in Ref 9,P 265 as follows: Note: Some ingredients of foreign proplnts are
NC(13.l%N) 94.7, DNT 4.1, tin 0.5, cryolite 0,2 & not used in US compns. Examples: acardites,
EtCentr 0.5% urethanes or camphor(as stabilizers &
Italy, Used mostly double-base proplnts, such as auxiliary gelatinizes for NC; also, when used in
B allistite or Filite of the following compns: a) large amts, as flash reducers); hydrocellulose
NC(12.25%N) 64.0, DEGN 35.0 & EtCentr 1% b) (as flash reducers); waxes(for improving ‘
Nitrocellulose acetate(lO%N) 63.5, DEGDN 27.0, ductility); Mg oxide(as antacid); graphite(not
cellulose acetate 5.0 & EtCentr 4.5% and C) only as a glaze but aIso as a component uniformly
NC 55.0, Metriol Trinitrate 40.5, metriol distributed thruout the grains-probably to improve
triacetate 2.o & EtCenti 2.5%(Ref 9,P 265XSee burning characteristics). Some Ger proplnts
also in Ref 8a compns Balistite ordinaria, contained AN(as oxidizer), others dicyandiamide
Balistite a basso titolo, B alistite attenuata, (as cooling agent, to decrease erosion, Ref 10,p
Polvere NAC, Polvere FB, Polvere C-2 and Ger 144). One of the pre-WWII Ger proplnts
Solenite). Compn of one of the Ital single-base contained Amm oxalate-presumably to diminish
cannon proplnts is given in Ref 9,P 265 as danger of ignition during extrusion(Ref 8c)
follows: NC (12.5%N) 97.0, EtCentr 2.0 & DPhA (This section was reviewed by E. Costa, R. Trask &
1 .0% N. Liszt of PicArsn)
 C38

Refs: 1 )Marshall 1 (1917), 289-335 2)Brunswig drical with 7 longitudinal perforations, 1 in the center
(1926), 3-11 & 134-6 3)Marshall 3(1932), 85-96 of the grain and 6 at the vertices of a symmetrical hex-
4)Stettbacher(1933), 203 4a)Pepin Lehalleur agon (Ref 3)
(1935), 290-1 5)Hayes(1938),6-36 5a)Anon, E)Dirnensions of Grains are measured by means of a mi-
“Military Explosives”, TM 9=2900(1940), 20-83 crometer and a microscope with 25 diameters magnifica-
6)Davis(1943), 287-330 7)P~rez Ara(1945), 439& tions, as described in Ref 1, Method S34. 1.1 and in Ref
448-50 7a)Ohart(1946), 26 8)Vivas, Feigenspan 3, Method F- 4c. For Type I, the av grain length (L)
& Ladreda 3(1948), 94-225 8a)Belgrano(1952), shall be 2.10-2.50 times the av grain dkun (D), while
110-14 8b)Stettbacher, Ziirich, Switzerland; for Type II 3 to 6 times. For Type I, D=5 to 15 times
private communicational 954) 8c)M.M.Kostevitch, diam of perforations (d) and For Type II D=3d
Buenos Aires, Argentina; private communication F)Web Measurements. For Type I, the cliff betw the av
( 1954) 9)Anon, “Military Explosives”, TM outer web thickness (WO) and the av inner web thickness
9-191 O(1955), 218-66 & 329-32 9a)B.T.Fedoroff (Wi) shall not exceed 15% the average web
et al, “Dictionary of Russian Ammunition and thickness (Wa) and for Type II, the av of the web
Weapons”, PATR 2145( 1955)(Conf), Rus 5 & measuremerits above the median shall not differ
17-19 9b)Anon, “Ammunition General” TM from the av of the total measurements by more
9-1 900(1956), 33-42 10)B.T.Fedoroff et al, than 15%(Ref 3)
c‘Dictionary of Explosives, Ammunition and G)Compressibility of Grains. When grains of
Weapons’’(German Section) PATR 2510( 1958),pp Type I proplnt are subjected to a pressure
Ger 81 & Ger 140-9 10a) Anon, “Analytical sufficient to crack each grain, the av
Methods for Powders and Explosives”, AB compression shall be not less than 30%. The
Bofors, Nobelkrut(1960) Il)L.Shulman, et al, test is described in Ref 1, Method 505.1 and in
“Burning Characteristics of Standard Gun Ref 3, Method F-4d
Propellants at Low Temperatures(21° to -52 °C)”, H)Moisture and Volatiles Determinations. See
TechRept FRL=TR-41, PicArsn(1961) 12)US Ref 1, Methods 101.1.2 & 101.2.2
Specifications: FA-PD-26A; JAN-P-381, JAN-P I)Moisture Determinations. See Ref 1, Methods
-528, JAN-P-659, JAN-P-733, MIL-p-270A, 101.3.2 & 102.1.3
MIL-P-309A, MIL-p-323A, MIL-P-668A, MIL-P J)Volatiles Determination. See Ref 1, Methods
-20306, MIL-P-46489, OCA-PD-134, PA-PD-123 103.1.3 & 103.3.3
and P~-PD-329 13)Dr H. Walter, PicArsn; K)Residual Solvent. See Ref 1, Method 103.4.1
private communication 1962) L)Ash. See Ref 1, Methods 106.2.3, 106.1.2,
106.3.2 & 106.4.1
Cannon Propellants, Analytical Procedures. General M)Diphenylamine( DPhA). See Ref 1, Methods
requirements for US cannon proplnts tie given in Ref 3. 201.1.3, 201.2.3 & 201.3.3
They are as follows: N)E,thyl Centralite(EtCentr). See Ref 1, Method
A)fiygroscopicity. The amt of allowed hygroscopicity 202.2.2
is prescribed for each individual type of proplnt in one O)DietbylphtbaLzte(DE tPH). See Ref 1, Methods
of the Specs listed in Ref 4. Hygroscopicity is detd by 203.2.2 & 203.4.1
weighing a ltllg sample (contained in a tared dish) before P)Dibutylphtbalate( DBuPh). See Ref 1, Method
and after exposure to a humid atmosphere of 90% RH and 204.1.2
30°, for 4 days and then each day until chge in wt betw Q)Dirzitrotoluerze(DNT)Q See Ref 1, Methods
individual weighings will be no greater than 0.2mg. 205.1.2 & 205.2.3
This test is described in Ref 1, Method 503.2.2 and in R) Trinitrotoluerze( TNT). See Ref 1, Methods
Ref 3, Method F-4a 206.1.2 & 206.3.3
B)Stability. All single-bae proplnts shall be subject- S)Triacetin. See Ref 1, Methods 207.4.2 & 207.5.1
ed to 134.5° Heat Test and SH do~le- base ProPlnts to T)Nitroglycerin(NG). Ref 1, Method 208.2,2
1200 Heat Test. These tests are described in Ref 1, U)Nitrocellulose(NC). See Ref 1, Methods
Method 404.1.2, Ref 2,pp 31 & 33 and Ref 3, Method F- 209.2.2, 209.3.2 & 209.6.2
4e. Surveillance test ~ 65.5° is run f~ information V)Nitroguanidine( NGu). See Ref 1, Methods
only (Ref 2,pp 30-.2) 213.1.4, 213.2, 213.3.1 & 213.4
C) Ballistic Requirements shall be in accordance with W )Trietbyleneglycol Dinitrate. See Ref 1, Method
the Ballistic Appendix to US Army Spec 50-12-3 or 220.1
ButOr@ec O- S- 16666(Ref 3) X)Phtbalate Esters. See Ref 1, Method 221.1.1
D)Form o~ Grains. For Type 1, the grain shall be cylin- Y)Inorganic Salts. See Ref 1, Methods: 303.1.3
 c 39

(Potassium Perchlorate), 304.1 .2( Barium Cañone(Span). Cannon

Nitrate), 305.1 .l(Calcium Carbonate), 306.1.3
(Tin), 306.2 .2(Tin & Graphite), 306.3 .l(Tin), Cañone sin retroceso(Span). Recoilless gun
307.1 .2(Cryolite), 308.1 .3(Graphite & Carbon
Black) and 309.1.2& 310.3 .l(Carbon BIack)(See Canopus. An older Ital perchlorate blasting expl
US Specs listed in Ref4, for analysis of Re/.’ U. Alvisi, Rassegna Mineraria 37, 231(ca1912)
individual proplnts) & CA 7, 1974(1913)
Analytical procedures used at the AB
Bofors, Nobelktut plants in Sweden are described Canouil Powder. A priming compn patented in
in the Manual entitled “Analytical Methods for England ca 1860: K chlorate 35.5, Pb hydrosulfide
Powders and Explosives”, Bofors(1960), pp & Pb ferrocyanide 28.3, glass pdr 35.5 and
169-90) amorphous pho sphoms O.7%. The ingredients
(This section was reviewed by Dr H.Walter of were mixed with water to form a paste which was
PicArsn) shaped into pellets and dried
R efs: l)Anon, ‘<Propellants, Solid: Sampling, Re/s: l)CundiH(1889) in MP 5, 303(1892) 2)
Examination and Testing”, Military Standard Daniel(1902), 108
MIL-STD-286A( 1960) 2)A. J .Clear, “Standard
Military Procedures for Sensitivity, Brisance and Capacity of Bomb or Projectiles. The ratio of
Stability of Explosives”, TechRept FRL-TR.25, the wt of expl in a bomb or projectile to the total
PicArsn, Dover, NJ(1961) 3)US Specification wt of missile, expressed in percent, is called its
MIL-P-270A, “Powder, Propellant, Cannon 4) capacity
US Specifications: FA-PD-26A, JAN-P-381, Aerial bombs may be subdivided into HC
JAN-P-528, JAN-P-659, JAN-P-733, MIL-P-270A, (high capacity) ca 80% capacity, MC(medium
MIL-P-309A, MIL-P-323A, MIL-P-668A, MIL-P capacity) ca 50% and LC(1OW capacity) below
-20306, MIL-P46489, OAC-PD-134, PA-PD-123 50%, more Often 5-30%
and PA-PD-329 Ref: A. B. SchiIling, PicArsn; private communica-
tion ( 1962)
Canon(Fr). Cannon
Cap, Ballistic. See Ballistic Cap
Canon antiaérien(Fr). AA(antiaircraft) gun
Cap Blasting, See Blasting Cap
Canon antichar(Fr). A/T(antitank) gun
Cap of an AP (armor- piecing) Shell. See Vol l,p
Canon a tuyére. Fr name for Hoch- and A483
Niederdrukkanone, described in PATR 2510
(1958),p Ger 90 Capexco Powder. An older coal-mine expl: NG
32-34, Amm oxalate 30-32, Na nitrate 24-25,
Canon de campagne. Field gun woodflour 8-10 & NC 0.5-1.5%
Re/: l)CondChemDict( 1950), 288(not listed in
Canon de gros caliber(Fr). Heavy gun (Large c al-~ Iater editions)
iber gun)
Capped Projectile. Same as Armor-Piercing
Canon de place(Fr ) Fortress cannon Capped(APC) Projectile. See Vol 1,p A483

Canon de siège(Fr). Siege cannon n-Caproylhydroperoxide. Same as n-Peroxyca-

proic or n-Percaproic Acid
Canon lisse(Fr). Smooth-bore cannon
Caprylene and Derivatives
canon obusier(Fr). Howitzer Cuprylene. The compd described in Beil 1, 221 is
probably a mixt of l-Octene(a-Octy lene),
Canon san recul(Fr). Recoilless gun CH~ [CH2 ] .CH:CH2 and 2-Octene(@ctylene),
CH3. [CHZ!4.CH:CH.CH3
Canon torpille(Fr). Torpedo gun x-~ononitrocap~len e or x- Nitro5ctylen e,
CeHt ~.N02; mw 157.21, N 8.91%; iiq, prepd by
 c 40

nitrating caprylene with moderately strong nitric (Ref 1). Its Silver Salt, Ag2N.CO*N~, wh
acid flakes, expl violently from heat or fricyion
Ref: Beil 1, 222 Re/s: l)Beil 3, 129, (59), [102] & {239} 2)
x,x-Ditrocaprylene or x,x.-Dintroöctylene, J .Thiele & O.Stange, Ann 283, 37(1894) 3)
C* H14N204; mw 202.21, N 13.86%; Iiq decg on C.D.Hurd & L.U.Spence, JACS 49, 268(1927)
boiling; was prepd by two-stage nitration of 4) R. Hofsommer & M. Pestemer, ZElektrochem
caprylene. Its expl props were not detd 53, 385(1949)(UV absorption spectra)
Refs: l)Beil 1, 222 2)J .Bouis, Ann Chim Phys Mononitrocarbamic Acid(called Nitrocarbamid-
[3] 44, 77(1855) 3)CA 1907-1956-not found s%-ue or Nitramid-carbons5ure in Ger),
Tri-, Tetra- and Pentanitrocaprylenes 02 N. NH, COOH; mw 106.04, N 26.42%; known
-not found in Beil or in CA thru 1956 in the form of salts, some of which expl:
Potassium salt, 02 N. NK. COOK, wh ndls,
“Cap Sensitive” Explosive is any expl compn expl on heating; was prepd by nitration
which can be efficiently initrated by a commercial of urethane and subsequent hydrolysis
detonating element, such as a blasting cap or of the nitro ester by alcoholic KOH. This salt
detonating cord gives, on treatment with dil acids, the expl
Re/: Dr I. A. Grageroff, New York; private Nitroamide, H2N.NO(qv)
communicati0n(1955) Re/s.’ l)Beil 3, 124 & { 235} 2) J. Thiele &
A. Lachman, Ann 288, 295(1895) 3)Davis(1943),
Carocteristique, Produit(Fr). See Berthelot’s 369 4)K.W.F.Kohlrausch & H.Wittek,
Characteristic Product ActaPhysAustriaca 1, 299, 302(1948) & CA 42,
6665( 1948)( Raman spectra)
Caracteristiques des Explosifs(Fr). See Carbamic Acid Esters. The general formula
Characteristics of Explosives of these esters is H21%COOOR, where R is any
alkyl or aryl radical. They can be prepd by one
Carbamic Acid and Derivatives of the following methods: a)action of primary
Carbamic Acid; Amidocarbonic Acid or or secondary amines on esters of chloroformic
Aminoforrnic Acid(called Carbamids~ure; acid; for example, methyl chloroformate &
Kohlens~ure-monoamid or Aminoameisens~ure in aniline yield the methyl esters of phenylcarbamic
Ger); H2N.COOH; mw 61.04, N 22.95; the acid, or methylphenyl carbamate, C6Hs.NH.C00.-
theoretical, first & simplest aminoacid known in CH3 b)action of alkali salts of phenol on
aq solns, are called carbamates, and other urea chloride; for example, sodium phenate &
derivs. The prepn & props of aq solns of diphenylurea, both in alc soln, yield
carbamic acid and its salts are described in dipthenylcarbamate, (C6H5 )2 N.CO0.CeH~ C)
detail in Refs 1 & 2. See also Refs 3 & 4 action of alcohols or phenols on aromatic
Some of the derivs of carbamic acid are isocyanates; for example, phenol &
exDl
L
phenylisocyanate, when heated with a small amt
Re/s: l)Beil 3, 20, (9), [18] & {39} 2) Gmelin, of AICl~, yield phenyl phenylcarbamate}
Syst Nr 22(1937), 868 & 23(1936), 348-50 3) CeH5.NH9COO*C6H5( Ref 4)
Sidgewick, OrgChem of N(1937), 272 4)V. Nathan et al(Ref 1) examined a number of
Grignard, Edit, “Trait~ de Chimie Organique”, carbamic acid esters and concluded that the best
Masson, Paris, VO1 14(1949), 1-398(A .Guillaumin, stabilizing action on NC is obtd with compds in
D +riv~s azot4s de l’acide carbonique) which at least one H atom is replaced by an
Carbamyl Azide; Carbamoyl Azide or Azidoformam- aryl radical. Davis(Refs 2 & 5) examined
i de(called CarbarnidsHureazid; Azidoameisens%re several comps for their gelatinizing effect on NC
amid or Kohlensa”tie- amid- azid in Ger), Refs: 1 )I?.L.Nathan et ai, BritP 12743(1912) &
HZN. CO. N,; mw 86.06, N 65. 10%; ndls(from CA 7, 3842(1913) 2)T.L.Davis, IEC 14, 1140
Iigroin), prisms(from eth), mp 92-7°, dec at (1922) 3)Franklin(1935), lllff 4)Sidgewick,
110-20°, expl on heating rapidly or in contact OrgChem of N(1937), 272 5)Davis(1943), 322
with Cu powd; v sol in ale; sol in w(with decompril;
mod sol in eth or ligroin. Can be prepd by Carbamic Acid Ethyl Esters or Urethanes(called
treating a cooled HC1 sol of semicarbazide, Carbamids&re-~thYle ster or Lketh an in Ger),
H2N.C0.NH.NH2, either with aq NaN02 or with H2N.CO0.C2H5; mw 89.09, N 15.72%; CO1 lfts,
fumes of nitrous gases and by other methods mp 49-50°1 bp 180°; SOI in w, ale, eth, glycerol

1
 c 41

or chlf; SI sol in olive oil; other props & methods Some of its safts are expl: Ammonium salt,
of prepn are given in Beil(Ref 1) yel lfts, mp 105-200 with violent decompn;
Urethane was proposed in Germany and Potassium salt, yel powd, expl violently on
later in England as a stabilizer for NC(Ref 7). heating, by friction, or when brought in contact
According to Davis(Refs 6 & 8), it is only a with w; perfectly stable in dry air; and Silver
weak gelatinize for NC. Nathan et al(Ref 2) salt, AgC3H5N203 ~ yel powd, expl when heated;
prepd several metallic salts & other derivs and insol in w or AcOH; sol in NH40H or mineral
patented them as stabilizers & gelatinizes in acids(Refs 1 & 2)
NC-NGexpls. According to Nathan eta1(Ref3) Re/s: l)Beil 3, 123 & (59) 2) J. Thiele & A.
urethanes with two substituted H atomsr at Lachman, Ann 288, 304(1895) & JCS 701, 208
1east one of which is an aryl groups, for example,
(1896) 3)A.HantzsCh & J .Lifschitz, Ber 45,
rnetbylpbenyl urethane, [(CH9)N(C6H5 ).COO<2H~ ] 3030( 1912 XAbsOrptiOn spectra) 4)Davis(1943),
are better gelatinizes than those with only one 322
substituted H atom. Still better results are obtd
when urethane contains two aryl groups, for Nitrocarbamic Acid Ethyl Ester; Carboethoxynitro.
example$ pbenyl-bensylurethane, mine or Nitrourethane, OZN.NH CO0.C2H5; mw
[(C6HS)N(H2C.C6H, )C00<,H5] (Ref 5). 134.09, N 20.89%; lfts(from ligroin) or pltlts(from
Rintoul et al(Ref 5) proposed the use of eth+ Iigroin), mp 64°; v sol iri alc or eth; sol in W;
benzyl-p-tolyl-urethane, v S1 sol in Iigroin; was prepd by nitration of
[(C~H5.CH2)N(C6H4,CH3 )C00,C,H5 ], and urethane(Refs 1 & 2). Other props are given in
benzylurethane, [ (CGH5.CH2. NH.COO~C2H5 ] , Beil
as gelatinizes & stabilizers It forms saIts some of which are probably
In blasting gelatin contg at least 50% NG, expl: Ammonium salt, NH4C3Hg N204, crysts(from
one compn proposed by Rintoul et rd(Ref 4) ale), mp 171°; Mercuric salt, Hg(C3H~N204 )2, wh
contd NG 91.6Y NC 7.5, Ca C03 0.6 & powd; Potassium salt, KC3HSN204, large prisms
urethane 0.3%. The same inventors(Ref 5) (from hot w); and Silver salt, AgC3H5N20A,
patented propellant compns contg NC 50, NG 41, microsc ndls Y mp ca 80°; very sol in alc or w
phenyl-benzylurethane 8 & diphenylurethane 1% (Ref 1)
and NC 50, NG 41, benzyl-p-tolylurethane 8.5 & Refs: l)Beil 3, 125,(59), [99] & {236} 2)J.
ethyl-~ -naphthyl ether O. 5% Thiele & A.Lachman, Ann 288, 287(1895) 3)R.N.
Re/s: l)Beil 3, 22, (9), [19] & {41} 2)Sir Jones & G.D.Thorn, CanJRes 27B, 849(1949)(UV
F. L.Nathan et al, BritP 12743(1912) & CA 7, absorption spectra)
3842(1913) 3)Sir F .L.Nathan et al, BritP Carbamic Acid Methyl Ester; ’’Methylurethane’,
4941(1913); USP 1090-644(1914) & CA 8, Methylcarbamate or Urethylan(called Carbamidsliure-
1672, 2807(1914) 4)W.Rintoul & Nobel’s Expl methylester or Urethylan in Ger), H2N.COO<H~;
Co, BritP 14655(1915) & CA 13, 1639(1919) 5) mw 75.o7, N 18.66%; eIongated tablets~ mp 52-6°,
W.Rintoul et al, BritP 131389(1918) & CA 14, bp 176.7-77.7° at 760mm press, d 1.136 at 55.6°;
350(1920) 6)T,L.Davis, IEc 14> l140(1922) 7) other props & methods of prepn are given in BeiI
Marshail 3(1932), 99 8)Davis(1943), 322 9) (Ref 1)
CondChemDict(1961), 1195 Its Mercuric Hydroxide deriv,
HOd4g.NH-C00~C2H~, prepd by treating an alc of
Nitrosocarbamic Acid Etyyl Ester; Carboethoxyni- soln of equimolar quantities of urethylan &
trosamine or Nitrosourethane( called N-Nitrosocar- mercuric acetate, is obtd as yel scales which dec
bamids~ure-i$thy lester or Nitrosourethan in Ger), on heating(Ref 2)
0N.NH=O@C2H~ or HO*N:N*CO0.C2H~; mw Refs.’ l)Beil 3, 21, (9), [18] & {40} 2)A.
11.09, N 23.72%; yel ndls(from ligroin)~ mP~ec ca Pieroni, Gazz 41 II, 754(1911) & JCS 10Z I,
40° & dec completely 51-2° yielding aCetalde- 245(1912)
hyde; v sol in ale, eth, MeOH & acet; sol in w; S1 N.Chlorocarbamic Acid Methyl Ester,
sol in ligroin; was obtd on reducing the Amm C1*NH.CO0.CH3; mw 109.52, N 12.79%; trysts,
deriv of nitrourethane with Zn dust & AcOH mp 32°; readiIysoI in w or common ofg SOIVS;
(Refs 1 & 2). Davis(Ref 4) gives Pats of ester other props & method of prepn are given in Beil
required for complete gelatinization of 100ps of (Ref 1)
PyrocelIulose as 140 when dissolved in alc or 80 Its Ammonium salt, H,N. NCI.COO. CH,,
when in benzene is very unstable and expl spontaneously at OO;
 C 42

Silver salt, Ag.NCl. COO. CH$, powd, defgr ca Carbamyl Azide. Same as Carbamoyl Azide
40° but can be kept under w for several days; and
Sodium salt, Na NCI. COO. CH,, powd, defgr ca 3-Carbamyl-5-cyano-2-.diazo-4,6=dinitrophenol
115°(Ref 2) or 3-Carbamyl.5-cyano-2-diazo-4,6.dinitrobenzo-
R efs: l)Beil 3, {41} 2) P. Chabrier, AnnChim quinone [called 4.6-Dinitro-2-diazo-phenol-
(Paris) 17, 360-62(1942); CR 214, 363(1942) & CA dicarbons2iure-(3 .5)-amid-( 3)-nitril-(5) or 4.6
37, 3737(1943); CA 38, 3256(1944) -Dinitro-benzochinon-( 1.2)-diazid-(2)-dicarbon-
Nitrosocarbamic Acid Methyl Ester; Carbomethoxy. s3ure-(3.5)-amid-( 3)-nitril(5) in Ger] ,
nitrosamine or Nitrosourethylan( called N-.Nitroso-.
c arbamids~ure--methy lester or Csrbomethoxydiazo-
hydrat in Ger), ON. NH. CO0.CH3 or HO. N: N.-
COO. CH,; mw 104.07, N 26.92%; yel ndls (from eth+
Q2N.C=
I
z –C.kN
II or
NC.C= ~—C.C0.NH2
ligroin),mp 61 °(dec); v sol in w;decompd by boiling
w; expl in contact with dry HC1; was prepd by N02
treating the Amm salt of the methyl ester of
nitrocarbamic acid with Zn dust & glac AcOH
(Refs 1 & 2). It forms salts, some of which are $
expl: Amm salt, NH4C2H3N203, yel powd, mp dec 02N .C– t–C:N+ i’
105°, dec in aq soln; and Silver salt, I
NC.C— C=C.C0.NH2
I
AgC2H3N203, Y el ,powd, dec quickly in light$
1
expl on heating, by impact or friction(Refs 1 & 2)
NOZ
Refs: l)Beil 3, 123 2) J. Thiele & F.Dent, Ann
302, 251(1898) & JCS 761, 14-15(1899) mw 278.14, IS 30.22%; ref crysts(from dil AcOH),
Nitrocarbamic Acid Methyl Ester; Carbomethoxyni- mp expl 160-65°, readily sol in alc~ acet or
tramine of Nitrourethylan, 02 N. NH. CO0.CH3; mw AcOH; S1 sol in hot w; insol in cold w, benz,
120.07, N 23.33%; col pltlts or prisms, mP 88°, eth$ or chlf. Was obtd with other products by
dec ca 120°-300; was prepd by nitration of diazotizing isopurpuric acid,
urethylan(carbamic acid methyl ester) with ethyl [HO(02N)2(NC)2NHOH], with NZiN02 & coned
nitrate & H2S04 below -5 °(Refs 1 & 2) and by H2S04 in AcOH
other methods(Ref 3) This compd couples with a-naphthol in an
It forms salts which are probably expl: alcoholic AcOH soln to form an azo dye, which on
Ammonium salt, NH4C2H3N204, CO1 ndls(from acidification of the Na salt yields an extremely
warm w); dec on boiling in w or alc NH3; expl compd, 5, 7-dinitro.8-bydroxy-4 -oxy-6-cyarzo
Mercuric salt, ndls(from boiling w); Potassium -3, 4-dihydro-(benzo-1,2,3-triazene), (Beil 26, 316)
salt, KCZH3NZ04 ~ ndls or prisms(from w); and
Silver salt, AgC2H3N204, ndls, dec on boiling
in alc(Ref 1) OH
Refs: l)Beil 3, 125(59) 2)T.Thiele & F. Dent, OzN.t=/– C–h=fi
8
Ann 302,”249(1898)
H. J. Backer, Rec 31, 12(1912)
& JCS 76 I, 14-15(1899) 3)

NC. C=?
II I
—C—CO-NH
6
Carbamide. Same as Urea !V02 l4 3

Carbamidine. Same as Guanidine

Re/.s: l)Beil 16, [300] 2)H.E.Fierz & H.
Carbamite. Same as sym-Diethyldipheny lurea, Briitsch, HeIv 4, 2431(1921)
Centrality 1, or Ethyl Centralite(See under
Centralizes) 3-Carbamyl-5-cyano-2-diazo-6-nitro-hydroqui-
none or 3-Carbamyl-5-cyano-2-diazo-6-nitro-4
Carbamoyl Azide. See under Carbamic Acid -hydroxybenzoquinone [called 5-Nitro-3-diazo-
hydrochinon-dic arbonsihre-( 2.6)-amid-( 2)-nitril-
Carbamyl or Carbamoyl. The monovalent radical (6) or 6-Nitro-4-oxybenzochinon-(1 .2)-diazid-(2)
H2N.CO- derived from carbamic acid, H2N,COOH -dicarbons%ure-(3. 5)-amid-( 3)-nitril-(5)- in Ger]
 c 43

p-nitrosoaniline & semicarbazide in dil AcOH

R e/s: 1 )Beil 16, (412) 2)0. Fischer, JPraktChem
92, 73(1915) & JCS 108, 909(1915)
or
[I(or N’)-Carbamyl-III(or N)-hydroxy-III(or N)
OH -(p-dimethylaminophenyl)] -triazene { called
3- [4-Dimethylamino-phenyI] -3-oxy-triazene-(1)
o -carbon silure-(1)-amid in Ger },

02N.C–/– C:N+:N” H2N.C0.N:N.N(OH) .C6H4.N(CH3)2;

N 31 .38%; grn-yel ndls(from AcOH, dil pyridine
mw 223.23,

Nc:.—=c :CONH or coned formic acid), mp expl ca 180°; sol in

/“”2 AcOH; S1 sol in w, ale, eth or benz; was prepd
from p-nitrosodimethy laniline & semi-
OH
carbazide in dil AcOH with cooling(Ref 1 & 2)
mw 249:14, N 28.11%; similar in all its props to
(See also Ref 3)
the above dinitro deriv; obtd on evaporation of the
Re/s: l)Beil 16, (413) 2)0. Fischer, JPraktChem
mother liquor from the prepn of the above dinitro
92, 72(1915) & JCS 108, 909(1915); 95, 267
deriv
(1917) & JCS 1121, 708(1917) 3)A.Angeli & Z.E.
l?e~s: l)Beil 16, [300] 2)H.E.Fierz & H.
Jones, Ber 62, 2100(1929)& BrA 1929A, 1290
Briitsch, Helv 4, 378(1921) & CA 15, 2431(1921)
Carbamylic Ester. Same as Phqnyl Urethane
[l(or N’)-Carbamyl-II(or N)-guanyl]-triazene
[called Triazencarb ons2ure-(1)-amid Carbanilic Acid and Derivatives
-carbon s%ure-( 3)-amidin or Triazendicarbon s%ure Carbanilic Acid or Pbenylcarbamic Acid(called
-amid-amidin in Ger] , Carbanils3ute; Phenylcarbamidsliure or
H2N. CO*N :N.NHcC( :NH).NH2; mw 130.12, N Anilinoameisensliqre in Ger), C6H5 .NH.COOH; mw
64. 59%; yel ndls with H20(from hot w), mp defgr 137.13, N 10.21%; exists in the form of salts &
at 139° without melting, explodes at 95° on other derivs, some pf which are expl
prolonged heating; readily sol in aIkalies, Ref: Beil 12, 319, (218) & [184]
giving -a yel color; diffc sd in w. Was prepd by Carbanilic Acid Azide; Carbanilinoazide or
either neutralizing an aq soln of the Phenylcarbamoylazide( called Carba.nils2iureazid
hydrochloride of above triazene or gently warming in Ger), C6H5.NH.C0.N3;. mw 162.15, N 34.56%;
the carboxylic acid ethyl ester of the above lfts(from alc + w), mp ca 103-4°(to a red liq); VOI
triazene, [C2H~OOC-N:N-NH. -C(:NH).NH2 ], with in steam; readily sol in ale, eth, chlf or benz;
ammonia insol in w; other props & methods of prepn are
It forms salts, some of which are expl: given in BeiI
Hydrochloride, C2H6N60+HC1, wh trysts, mp Ref.’ Beil 12, 386, (242) & [224]
defgr at 13,9° without melting, explodes at
100-110° on prolonged heating; was prepd by Trinitrocarbanilic Acid Esters. Various esters,
slowly adding diazoquanidine ~ their derivs & some salts of trinittocarbanilic acid
[NC.N:N.NH.C(:NH) :NH2 ], to Hcl at 60-700 and are listed in Beil, including the ethyl & methyl
Nitrate, CZH6N60+HN03, shiny trysts, mp expl esters described below
at 136° without melting(Ref 1 & 2)
Refs: l)Beil 3, 128 2) J. Thiele & NO@ botne, Ann Trinitrocarbanilic Acid Ethyl Ester or
305, 71-4 & 77-8(1899) Picrylurethane(called 2.4.6-Trinito-carbanilsihre
-iithylester or P ikrylurethan in Ger),
[I(or N’-Carbamyl-lII(or N)-hydroxy-lII(or N) (02N)9C~Hz.NH.C00. C2H~; mw 300.19, N 18.67%;
-(p-aminophenyl)] -triazene {called 3- [4-Amino lt yel ndls (from dil ale) or pltls(from coned ale),
-phenyl] -3-oxy-triazen-(1 )-carbons ~ure-(1).amid mp 144-47°; can be prepd by nitration of carbanilic
in Ger}, HZN.CO.N:N.N(OH) .C6H4 .NH2; mw acid ethyl ester or of mono- & dinitroderivs and by
195.18, N 35.89%; yel ndls(from AcOH), mp dec other methods. Its expl props were not reported
above 200°, expl oh heating rapidly; readily sol Re/: Beil 12, 768, (370)& [423]
in AcOH or dil pyridine; diffc sol in most org
SOIVS; decompd in dil H2S04; was prepd from Trinitrocarbanilic Acid Methyl Ester or
 I

c 44

Picrylurethylan( called 2.4.6-Trinitro-carbanils3ure (02N)2C6H3.NH.C0 .NH.C6H5; yel ndls (from

-methylester or Pikrylurethylan in Ger), acet), mp 186-7’0 (dec); readily sol in acet or warm
(02N)aC6H2.NH.C00 .CH3; mw 286.16, N 19.58%; ale; sl sol in hot benz, chlf petr eth or w; diffc
almost COI ndls (from alc + AcOH), mp 192-96°; sol in eth; is described in Refs 1 & 2. Other
was prepd by nitration of carbanilic acid methyl dinitro derivs are listed in Ref 3
ester and by other methods. Its expl props were Re/s: l)Beil 12, [410] 2) L. C. E. Kniphorst, Rec
not reported 44, 719-20(1925) 3)C.Naegeli et al, Helv 21,
Ref: Beil 12, 767 & [423] 1140(1938) & CA 33, 541(1939)

Carbanilide and Derivatives Trinitrocarbanil ide, Cl ~H9N507; mw 347.24, N

Carbanilide; N, N’ -or 1,3-or sym-Dipbenylurea 20. 17%. Several trinitro derivs of carbanilide are
(called N,N’-Diphenyl-harnstoff or Carbanilid in described in Refs 2 & 3. Their expl props were
Ger), C6H5.NH.C0.NH.C6 H~; mw 212.24, N not reported
13. 20?4. This compd is described under BIS Re/s: l) Beil-not found 2)P.T.Sah & Tsu-Sheng
<OMPOUNDS as N, B’-Bis(phenyl)-urea in Vol 2 of -Ma, JChineseChemSoc 2, 159-66(1934) & CA 29,
this Encyclopedia 465(1935) 3)C.Naegeli et al, Helv 21, 1140(1938)
Note: N,N- or asym-Diphenylurea, called Acardite & CA 33, 541(1939)
1, is described in Vol I,p A7-R
Nitrosocarbanilide or N-Nitroso-N, N’ Tetranitrocarbanil ide, C, ~H8N609; mw 392.24,
-diphenylurea, C6H~ .N(NO)L0.NH.C5H5; mw N 21.43%. The N. N’-Bis (2,4-dinitro-) & N,N’
241.24, N 17.42%; yel powd, mP 82 °(dec); sol ‘n -Bis (3,5 -dinitrophenyl)-urea derivs are described
eth, alc or AcOH; dec on heating in alc or benz; under Bis (Phenyl)-urea and Derivatives.
other props & methods of prepn are given in Beil & The following isomers are also known: 3,3,
in Ref 2 x, x-Tetranitrocarbanil ide, yel nds; prepd by
Re/s: l)Beil 12, 583 & [312] 2) J. W. Haworth & nitration of 3,3’ -dinitrocarbanilide (Refs 1 & 2);
D. H.Hey, JCS 1940, 361-9 & CA 34, 3699(1940) .2,4, 6,3’- Tetranitrocarbanilide, mp 164° (Ref 3);
Dinitrosocarbanil ide or N, N’-Dinitroso-N, N’ and 2,4,3’,5’-Tetranitrocarbanilide, mp 215°
-diphenylurea, C6H5.N(NO).C0.N( NO).C6H ; mw (Ref 3). Their expl props were not reported
270.24, N 20.73%; yel ndls, mp dec ca 1035; sol in Refs: l)Beil 12, 707 2) T. Curtius et al,
common org SOIVS; was prepd from carbanilide by J PraktChem 52, 230(1895) 3)C.Naegeli et al,
the action of nitrogen oxide in ACOH or by NaN02 Helv 21, 1141(1938) & CA 33, 541(1939)
in coned AcOH. Other props are given in the Refs Pentanitrocarbanilide, Cl ~H7N701 , ; not found in
Refs: l)Beil 12, [312] 2) H.Ryan & P. K. O’Toole, Beil or in CA thru 1956
SciProcRoyDublinSoc 17, 145-48(1923) & CA 177
1792(1923) Hexanitrocarbanilide, Cl ~H6N801 ~; mw 482.24,
N 23.24%. The 2,4,6,2’,4’,6’-hexanitro isomer or
Mononitrocarban ilide, 02 N. C6H4.NH.C0.NHOC6 H5; N, N’-Bis( 2,4,6-trinitroph enyl)-urea is described
mw 257.24; N 16.34%. Three isomers are described under Bis(Phenyl)-urea and Derivatives. This
in the literature: 2-Nitrocarbanilide, yel ndls compd is a high expl
(from w or ale), mp 170° & 231-33° (Refs 1 & 5);
3-Nitrocarbanilide, lt-yel ndls, mp 197.5-98.5° Carbanil ide; N, N’-Dibutyl. See Butylcentralite
(Refs 2 & 4); and 4-Niirocarbanilide, trysts (from under CENTRALIZES
dil ale), mp 202-12° (Ref 3). Other ProPs &
methods of prepn are given in the Refs Carbanilide; N, N’-Diethyl. See Centrality 1
Re/s: l)Beil 12, 694 2)Beil 12, 706 & [381] 3)
Beil 12, 723 4)M.S.Kharasch, JACS 43! 1893 Carbanilide; N, N’-Dimethyl. See Centraiite 2
(1921) 5)C.Naegeli et al, Helv 21> 1140(1938 &
CA 33, 541(1939) Carbanilide; N-Ethyl-N’-methyl. See Centrality 3

Dinitrocarbanilide, 02 N.CGH4.NH.C0.NH.CGH4 Carbanil ide; N-Methyl-N’-tolyl. See Centrality 4

.N02; mw 302.24, N 18.54%. The three isomers
are described as N, N’-Bis (monoitrophenyl )-urea Carbazid. One of the Ger names for Carbonyl
under Bis(Phenyl)-urea and Derivatives Azide or Carbonyl Diazide described in Vol I,p
The N-Pberzyl-N’-(2, 4-dinitropbenyl)-urea, A528-L

—— .—
!
 c 45

Carbazide. Acompdcontg thedivalent radical Cislak & A. L.Kranzfelder, USP 2456378(1948)&

-NH.NH.CO.NH.NH-. Serni-carbazide is acompd CA 43, 1808( 1949)( Prepn of carbazole by oxidn of
contg the monovalent radical H2N.C0.NH,NH- p-aminobiphenyl in vapor phase) 1 l) C. Conover,
USP 2479211(1949) & CA 43, 9086( 1949) (Synthesis
CARBAZOLE AND DERIVATIVES of carbazole by oxidn of o-aminobiphenyl in
Carbazole, 9.Azafluorene, Dibenzopyrroleor presence of trysts alumina hydrate) 12)Kirk &
Dipbenyleneirnine( called Carbazol, Dibenzopyrrol Othmer, 5, (1950), 26& 7(1951), 436,705,846 13)
or Diphenylenimin in Ger), C6H4— CGH4; mw Karrer(1950),788 14)Elderfield 3(1952), 291-341
INHZ 15)T.E.Jordan, “Vapor Pressure of Organic
167.20, N 8.38%; CO1 Ifts or pltlts(from xylol or Compounds”, Interscience, NY( 1954), Chapter 7 ,p
by subln), mp 245°, bp 355°, d 1.10 at 18°, vap 187 & plate 14 16)W.C.Sumpter & F. M. Miller,
press 400mm at 323°. Carbazole is one of the “Heterocyclic Compounds with Indole and
principal ingredients of the anthracene fraction of Carbazcde Systems”, Interscience, NY(1954),
coal tar distilling between 320 and 360°; it can be 70-109 ‘17)P.Tavernier & M. Lamouroux, MP 39,
separated from other constituents by various 355( 1957) (Thermochem values) 18)Sax(1957),
methods, one of which is fusion with KOH and 435( Toxicity) 19)CondChemDict( 1961), 215 20)
separation of the resulting deriv. Various methods US Spec MIL-C-13613@rd)
of separating or preparing carbazole are described Addnl R e/s: a)W.H.Rinkenbach, PATR 1480(1944)
in Refs l,5,7,9a,10,11,16 & others (Study of various stabilizers for single-base
Carbazole is a feeble base & an extremely proplnts showed that carbazole and Methylacardite
stable compd which is unchanged on prolonged are inferior to DPhA & Methylcentralite) b)
heating. It forms numerous salts & addn compds P. F. Macy, PATR 1641 (1947 )( Study of various
such as with perchloric acid, PA, TNB, TNT and stabilizers for double-base proplnts showed that
others (Ref 1) carbazole, Acardite I & EtCentr are superior to
Uses. Carbazole is used as a starting DPhA)
material for the manuf of dyes, insecticides and,
in France, as a stabilizer in NC proplnts, Accdg
to Davis(Ref 6), at temps of 60 to 75°~ carbazole
is not as efficient a stabilizer as DPhA or
Carbazole, Analytical Procedures. Carbazole
Centrality but at higher temps, such as 11,0°, it is
gives with isatin in coned sulfuric acid a blue
an excellent stabilizer(See also Ref 5a and
coloration(Ref 1). As an indole derivative, it
Addnl Refs a & b) gives a positive e‘pine-splinter test’ ‘(formation of
Derivs of carbazole which are themselves
a red color when a pine-splinter soaked in HC1
expl or used in expls are described below
soln is held in the vapor of an alc soln of
Refs: l)BeiI 20, 433, (162) & [279] 2)T.MXlark,
carbazole)(Refs la, 2 & 8). Carbazole may also
IEC 11, 204-09( 1919)( l%rification of catba~ole;
be identified by a bluish-green coloration
volubility in various SOIVS) 3)Ullamnn, 2nd ed, 3
produced when a trace of carbazole is dissolved in
(1929), 88-90 & 3rd ed, 5(1954), 76-80 4)Thorpe, coned sulfuric acid and a drop of nitric acid
Supplement 1(1934), 205 & 2(1938), 278 4a) is then added(Ref 8,p 72). Various other calori-
A.Douillet & H. Ficherodle, MP 27, 105-14 metric tests for carbazole are known, such as
(1937)( Volubility curves) 5) G. T. Morgan & described in Refs l,la,2,5 & 6 and Addnl Refs
L. P. Walls, JSCI 57, 358-62 (1938 )( Synthetic a,e,g,h & m
carbazole prepd by pyrolysis of o-xenylamine) 5a) Carbazole may also be identified as its
R. Dalbert, MP 28, 147-55 (1938 )( Comparison of picrate(red ndls, mp 1850), its addn compd with
stabilized NG proplnts)6)Davis( 1943), 310-11 7) styphnic acid(crysrs, mp 178.5 -179.5 °)(Ref 8,p 71)
V.Weinmayr, USP 2350940(1944) & CA 38, 5228 or its addn compd with l,3,5-TNB, mp ca 200.5°
( 1944)( Prepn of carbazole by heating p-aminc- (Addnl Ref n)
biphenyl & an org nitrosubstituted compd such as When carbazole is used in proplnts together
m-nitrobenz) 8)A.A .Morton, “Chemistry of with DPhA, it may be detected by dissolving the
Heterocyclic Compounds”, McGraw-Hill, NY(1946), mixt in benz, carefully adding(without mixing), a
141 9)S.J.Holt & V.petrow, JCS 1947>607-11 few drops of 70% sulfuric acid and then 1 drop of
(Properties of carbazoles, carbolines & related
3% hydrogen peroxide. If carbazole is present, a
compds) 9a)N.Campell & B.M.Barclay, ChemRevs green tinge appears at the interface of rhe two
40, 359-80( 1947)( Recent advances) 10)FoEo
 C 46

Iayers greyish-wh(when detd by visual inspection, as

Coulson & Biddiscombe(Ref 4) examined specified in 4.8)
the following methods for quantitative detn of Re/s.’ l)Beil 20, 435 & [ 281] la)G.Cohn ‘tDie
carbazole: a)Method based on an estimation of Carbazolgruppe”, Thieme, Leipzig( 1919), 31 &
nitrogen by Kjeldahl’s process(such as described 43 2)Thorpe, 2(1938), 278 3)V.Khmelevskii &
in Addnl Ref f) b)Cohns method based on the I.Ya.Postovskii, ZhPriklKhim 17, 463-70(1944) &
acetylation of carbazole, with subsequent titration CA 39, 3651(1945) 4)E.A.Coulson & D.P.
of excess AcOH(Ref l,p 31) c)Method based on Biddiscombe, Analyst 74, 46-51(1949)(7 refs) &
quantitative separation of carbazole as the N CA 43, 3746(1949) 5)T.C.J .Ovenston, JCSI 68,
-potassium dervative, followed by its decompn 54-9(1949) & CA 43, 5593(1949) 6)T.C. JOvenston,
and weighing the recovered carbazole(Ref 4,p 46) Analyst 74, 344-51(1949) & CA 43, 8138(1949)
and d)Ardsahev’s method of bromination (Addnl 7)W.A.Schroeder et al, IEC 43, 941-3(1951) 8)
Ref a). They came to the conclusion that none of W.C. Sumpter & F .M.Miller, “HeterocYclic
these methods is satisfactory. They also Compounds with Indole and Carbazole ,SYstems”,
examined the nitrosation method of Khmelevskii & Interscience, NY(1954), 71-2 9) Organic Analysis,
Postovskii(Ref 3) and found it satisfactory. In Interscience, NY, VOIS 1,2,3 & 4-not found
this method the sample contg carbazole is treated Addnl Refs: a)B .I.Ardashev, ZhPriklKhim 10,
with nitrous acid(generated from Na Nitrite & 1032-41)(1041 in Fr)(1937) & CA 32, 1612(1938);
AcOH) and the excess of nitrous acid is decompd RusP52893(1938) & CA 34, 5378( 1948)(Detn of
to produce NO, which is swept out in a stream of carbazole by titrating its AcOH soln with
carbon dioxide into strong KOH soln and its vol bromide -bromate reagent until the blue coloration
measured of I-starch paper remains for 10mins) c) M.11’inskii
C & B slightly modified the method of Kh & & R. B. Roshal, DoklAkadN 17, 117-20(1937)(in
P, and gave its detailed description(Ref 4,pp 47-51) Ger) & CA 32, 5335-6(1938) [Detn of carbazole by
(Compare with Addnl Ref k) treating with formaldehyde to form @-(hydroxymethyl)
Ovenston(Ref 5 & 6) described the -carbazole ] d)V. Khmelevskii & I. S. Levin, Prom-
chromotographic method of detng carbazole in OrgKhim 7, 308-10(1940) & CA 35, 3925(1941)
expls and proplnts. As the streak reagent, he used (Gasometric method for the detn of carbazole in
a 0.5% soln of K bichromate in 60% sulfuric acid crude anthracene) e)D.G.Harvey et al, JCS 1941,
which causes carbazole to turn green. A 154-5 & CA 35, 4769( 1941)( Carbazole in presence
paperchromatographic detn of carbazole is described of 2,3,4,5 - -tetrahydro-~-carboline-4-carboxylic
in Addnl Ref 1 acid in coned H2S04 produces a permanent dark
A gasometric method for detg carbazole is green coloration) f) E. Ruterberg, Bodenkunde u
described in Addnl Ref d and an infrared Pflanzenrfihr 26, 97-105(1941) & CA 37, 3013(1943)
absorption spectra method in Addnl Ref i (Detn of nitrogen in carbazole by a modified
A chromatographic analysis of proplnts K j eldahl procedure) g)V,Arreguine, RevUnivNacl,
contg derivs of carbazole~ such as nitro-, C6rdoba, Argentina 31, 1706-9( 1944) & CA 39,
nitroso-~ nitronitroso-~ and dinitro- iS described 3222( 1945)( Calorimetric method of detg carbazole
in Ref 7 using xanthydrol in AcOH-HCI soln) h)N ,Strafford
Requirements of the US Armed Forces for & W. LStubbins, Rec 67, 918-26(1948) & CA 43,
carbazole, used as a primary material for manufg 3747( 1949)(Detn of carbazole by means of
TeNCbz (tetranitrocmbazole) are covered by salicylaldehyde reagent; a blue coloration is
Specification MIL-C-136 13(@d), superseding PA produced) j) A. Pozefsky & I. Kukin, AnalChem
-PD-185(Ref 1). The requirements me: a)P~fitY 27, 1466-8(1955) & CA 50, 6257( 1956)( Group-type
-97.0%, minimum(when detd by K j eldahl method, nitrogen-hydrogen analysis of pyrrole-indole
as specified in proced 4,4) b) Freezing point -carbazole type compds by an infrared absorption
244.0°, min(when detd as specified in 4.5) method) k)E .Omori, NipponKagakuZasshi 77,152
Note: The app and procedure are similar to -4(1956) & CA 51, 17613 (1957 )( Quantitative
those given in Vol 1,pp A612-R & A61 3-L C) analysis of refined carbazole by nitrosation) 1)
As% Content-o. 10% max(when detd by incinerating T.Wieland & W. Kracht, AngChem 69, 172-4(1957) &
. .
a log sample in a muffle furnance, as speclfled CA 52, 173( 1958)( Paperchromatographic analysis
in 4.6) d)Moisture Content-o. 10%, max(when detd of mixts contg carbazole) m)G.Vanags &
by heating a 5g sample at 100-1050 to const Wt M.Mackanova, ZhAnalKhim 13, 485-6(1958) & CA
(ca 2hrs) as specified in 4.7) e) Color white to 53, 4022( 1959)( Color reaction of carbazole with
 c 47

2-nitro-l ,3-indandione) n) J. C, Godfrey, AnalChem (dec)(Ref 4); Carbazole-3-diazonium Chloride,

31 1088(1959) &CA 53, 15716( 1959)( 1,3,5-TNB Cl ~HaN3 ~Cl+2H20, yel ndls(from w), mp becomes
may serve as a quantitative reagent for carbazole grn at 98° & dec at 102°; the Anbydrous Chloride
because it forms a definite complex, mp 200.5° Salt, C H N .Cl, om-yel trysts, darkens at
and mol wt ca 380) 106-10~2an% ~ecomposes explosively ca 153°
(Refs 3 & 4); Carbazole-3-diazocyanide,
3-Azidocarbazole or Carbazole-3-azoimide, C6H4— C6H4 .N2 .CN, brick-red ndls(from 50%
CGH4— C6H3.N3; mw 208.22, N 26.91%; \NHz
\NH/
ale), becomes brn on exposure to light, mp dec ca
lustrous CO1 plates(from eth, alc or Iigroin), 155-60°, insol in common org solvs(Ref 3);
becoming bm on exposure to light, mp 176-77(dec Carbazole-3-diazonium iodide,
with violent evoht of gas); readily sol in common Cl 2H6N~.I+H20, yel trysts, become grn ca 73°,
org SOIVS; was prepd by treating carbazol-3 & decomp explosively ca 81°(Ref 4); and
-diazonium chloride with an aq soln of NaN3. Carbazole-3-dizon ium Nitroprusside,
When this compd is brought in contact with coned (HN:C1 *H7N2)2 [Fe(CN)~(NO)], It yel ppt,
H2S04, it decomposes with expl violence becomes brn on exposure to light, rep-when
Refs: l)Beil 20, [290] 2)G.T.Morgan & H.N. heated rapidly turn gm ca 150° and decomp with
Read, JCS 121 III, 2714-15(1922) expl at 160°(Ref 3)
Re/s: l)Beil 22, 590 [502,517] 2)0,Ruff &
3-Diazocarbazole or Carbazole-3-diazoimine, V. Stein, Ber 34, 1668, 1680(1901) 3)G.T.Morgan &
C6Ha— C H :N2; mw 193.20, N 21.75%; bright H. N. Read, JCS 121 II, 2711-14(1922) 4)S.H. Tucker,
\N# s 3
JCS 1251, 1145-48(1924)
orn-red ndls, decomp rapidly on exposure to
light; mp darkness at 80-90° & expl at 95°(when Nitrated Compounds of Carbazole
heated rapidly), but when the temp is raised The nitration of carbazole with nitric acid
slowly, it begins to darken at 80°, becomes brn of various strengths and at various temps or by
at 1050 and does not melt even at 300°; dissolves the use of H2S04 & HN03, produces
in w with a deep red coloration; attempts to nitrocarbazoles of various degrees of nitration.
recrystallize it from w resulted in decompn & Many refs are available on the nitration of
formation of a brn ppt, It was first prepd by Ruff carbazole but particular attention is called to Refs
& Stein(Ref 2) by treating an aq soln of carbazole 7,12 & 14. Some of the nitrated derivs of carbazole
-3-diazonium chloride with coned NaOH. The described in the literature ate the following:
compd first separated as a red oil and then turned 9 or N-Nitrosocarbazole, C6H4— C6H4; mw
into red ndls which were very expl & extremely \N/
sensitive to light. This compd was not properly
;0
identified by Ruff & Stein(Ref 2). Morgan & Read
196.20, N 14.28%, yel shinny ndls(from ale), mp
(Ref 3) prepd the compd later by the same method 82 °(Ref 1); 3-NitrosocarbazoIe, listed in Refs 5 &
and properly identified it
12 but no info on props available; 1-Nitrocarbazole
3-Diazocarbazole expl on heating, by impact
C6H4—- C H .N02, .mw~212.20, N 13.20%, yel
or by friction. It must be stored in the dark as the \NH/ 6 ~
compd is extremely sens to light
ndls(from glac AcOH), mp 187 °(Ref 2); 2
Refs: l)Beil 21, [279] 2)0.Ruff & V. Stein, Ber
-Nitrocarbazole, yel ndls(from benz with charcoal),
34, 1681(1901) 3) G. T.Morgan & H.N.Read, JCS
m’p 166-73 °(Refs 6 & 8); 3-Nitrocarbazole, yel
121 II, 2712(1922)
crysts(from xylol), mp 205-14°(Ref 3); 4
-Nitrocarbazole, yel-orn plates( sublimation), mp
Carbazole-3-diazonium Hydroxide and Its Salts,
179-83°(Refs 6 & 8); 9-Nitroso-3-nitrocarbazoZe,
CH —C H3.NZ.0H; mw 211.22, N 19.90%.
G 4\NH z G C6H4— C6H3.N02, mw 241.20, N 17.42%, It yel
\N/
The hydroxide exists only in soln which decomposes
rapidly on exposure to Iighq was obtd by diazotizing Jo
3-aminocarbazole with NsNOZ & HCI(Refs 1,2 & 3) ndls(from ale), mp 166-69( dec)(Ref 4); 1,6
Some of its salts which are unstable and -Dinitrocarbazole, 0zN.CeH3— C6Ha .N02, mw
expl include: Carbazole-3-diazonium Bromide, \NH~
C, ~HeN3.Br+2H 20, yel ndls(from w), mp 110° 257.20, N 16.34%, wh trysts, rep-chars betwn
 C 48

300-60° without melting; claimed to have been acetylcarbazole was treated with fuming IIN03.
isolated & probably identified from chromatographic In 1912 & 1913 Cassella & Co(Ref 6) obtd
props by Schroeder et al(Ref 9); 2, 6-Dirzitro- patents covering the manuf of polynitrocarbazoles
carbazole, yel ndls(from acet), mp 329-30 °(dec)Y by the process of dissolving carbazole in H2S04
detailed description of prepn given by and treating the soln of sulfonic acids with
Leditschke(Ref 11); same compd called “3,7 srrong nitrating agents. The crude product, thus
-Dinitrocarbazole” , mp 325-6°, by Smith & prepd, contained principally 1,3,6,8-TeNCbz
Brown(Ref 10); 3, 6-Dirzitrocarbazole, yel ndls (Ref 7) and about 10% of the 1,2,6,8-TeNCbz
(from nitrobenz), rep-darkens at 280 & melts ca i somer(Ref 15). The prepn & rnanuf of TeNCbz
335 °(Ref 4); 2, 7-Dirzitrocarbazole, yel ndls(from is described also by Raudnitz & H. Bohm(Ref
acet), mp 335-42 °(Refs 10 & 11); 1,3 8), Amemiya et al, (Ref 16), Livingston(Ref 12),
-Dinitrocarbazole, crysts(from xylene), mp 263°, Baer(Ref 17), Pfaff(Ref 10) and others
was prepd by heating l-(2,4 -dinitrophenyl) The TeNCbz isomers listed in Beil and in
-benzotriazole & m-DNB lhx at 270-90° in a salt some other Refs are as follows: a- Tetranitro-
carbazole, It-yel ndls, mp 285-86 °(EscaIes) &
-bath(Graebe-Ullmann synthesis)(Ref 13)
308 °(dec)(Ciamican & Silber); ~- Tetranitro-
Since mono- and dinitrocarbazoles are not
carbazole, lt-yel pltls(from glac AcOH), mp
expl, they are not described here in detail. For
273 °(Escales) & a product mp above 3200
addl info on props or methods of prepn the Refs
(Ciamician & Silber); y- or 1,3,6,8- Tetrarzitro-
given below should be consulted
carbazole, lt yel pltlts(from nitrobenz), mp
~e~s: l)Beil 20, 437, (166) & [285] 2)Beil 20,
285 °(Ziersch and Borsche & Scholten) or golden
439 & [288] 3)Beil 20, 440, (168) & [288] 4)
yel ndls(from glacial AcOH), mp 289 °(Raudnitz)
Beil 20, 440,441 & [289] 5)M.A.11’inskii et al,
or pale yel ndIs(from glac AcOH), mp 295.6
ZhKhimProm 5, 469-73(1928) & CA 22, 3888-9
- 296°(Murphy et al); and 8-Tetranitrocarbazole,
(1928) 6)N.Campbell & B.M.Barclay, JCS 1945,
yeI prisms(from glac AcOH), mp dec on heating
530 7)N.Campbell & B. M. Barclay, ChemRevs 40,
ca 200°(Escales and Ciamician & Silber)
359-80(1947) 8)G.N.Anderson & N. Campbell, JCS
The structure of these isomers, except
1950, 2904-5 9)W.A.Schroeder et al, IEC 43,
that of 1,3,6,8 -TeNCbz, has not been
941 ,943(1951) 10) P. A.S.Smith & B. B. Brown,
definitely established(See “Separation of
JACS 73, 2436-37(1951) 1 l)H.Leditschke, Chem-
Isomers from Crude Product” discussed beIow)
Ber 86, 522-24(1953) & CA 49, 8246(1955) 12)
Health hazards connected with the use of
W. C. S-umpter & F ,M.Miller, “Heterocyclic
TeNCbz as an insecticide(Ref 11) and of other
Compounds with Indole and Carbazole Systems”,
pesticides are discussed by Brieskorn(Ref 13)
Interscience, NY (1954),pP 81-5 13)
although Sax(Ref 19) reports that toxicity
B. St6rkovi5 et al, Chem Listy 51, 536-8(1957) &
details are unknown
CA 51, 10541(1957) 14)A.V.Topchiev,’’Nitration
The expl props(Ref 20) of TeNCbz
of Hydrocarbons and Other Organic Compounds”,
(principally the 1,3,6,8-isomers) have been
Pergamon Press, NY(1959),p 40
detd as follows: Brisance by Sand Test, 41 gms
Trirzitrorzitrocarbazo/e, Cl ~H6N406, Mw
sand crushed; Explosion Temperature, Co, 47o
300.20, N 18.54%; not found in Beil or in CA
dec in 5 sees; Impact Sensitivity, 2kg wt, 18
thru 1960
inches using 14mg sample & PA Apparatus;
Tetranitrocarbazoles( TeNCbz), Cl ~H5N~Oe; mw
Heat of Combustion, $:, 131O kcal/mol(Ref 18);
347.20, N 20. 17%. The nitration of carbazole or
Heat of Formatio% Qf-6.9 kcal/mol(Ref 18);
N-acerylcarbazole with strong HNO~ or by other
100°C Heat Test, % Loss 1st 48hrs 0.15, % Loss
means, produces a yel-colored expl product
2nd 48hrs 0.05, Explosion in 100hrs none;
which corresponds to the above empirical
Hygroscopicity at 30°C & 90% RH 0.01%;
formula. The product is now known to be a
Sensitivity to Initiation 0.20g LA & 0.25g
mixt which is difficult to separate into its
Tetryl reqd for 0.4g sample in 200g Sand Bomb
isomeric components(See below)
The prepn of TeNCbz was first reported in Uses: According to Pfaff(Ref 10), 1,3,6,
1880 by Graebe(Ref 2) who nitrated carbazole 8-TeNCbz(also called “Nitrosan”) has been
with 94% HN03. Similar procedures were used as an insecticide agaurst grape insects,
followed by Escales(Ref 4) and Ziersch(Ref 5). replacing arsenic prepns previously used. It
However Ciamician & Silber(Ref 3) observed was proposed, during WWII in Germany, a= .
that four isomers TeNCbz’s were formed when substitute for BkPdr in first fire compns for

1 —.
 c 49

illuminating flares. Due to its non-hydroscopic & with KOH soln, the product turned red
non-corrosive props, TeNCbz was expected to immediately, the color intensifying on heating
completely replace BkPdr in igniter compositions. The crude 8-compd could not be purified
To avoid destruction(deterioration & thus became by crystn
unserviceable) in storage of pyrotechnic No structure of these compds was
devices contg Mg, it was proposed to also established, except that of the 1,3,6,8-isomer
replace the BkPdr “intermediate” composition Borsche & Scholten(Ref 7) prepd
by the following mixt: TeNCbz 30, KNog40 & TeNCbz,(by heating tetranitrornethoxy biphenyl
Al powd 30% (Ref 21) with alc ammonia) as red-brn, thin prisms, mp
In the USA, TeNCbz has been studied at 285° and showed that it was mostly the 1,3,6,
PicArsn for use in ignition type powders (Ref 8-isomer
12 & 15) and for other components of Mmphy et al(Ref 15) investigated at
ammunition(Ref PATR 1984 & 2180) PicArsn crude TeNCbz prepd by sulfonation
and subsequent nitration of carbazole. They
Tetranitrocarbazole( TeNCbz). Separation of separated (by repeated fractional crystns from
Isomers from Crude Product. Four isomers: acetone), three fractiorls varying in their
a,~,y and b listed in Beil(Ref 1), were solubilities in acct. The most SOI of these
separated by Ciamician & Silber(Ref 3) and fractions, obtained in small amt, contained ca
later by Escales(Ref 4), but their structure was 13% N(compared with the calcd value of 20.17%
not established for TeNCbz). Based upon this analysis and the
The separation of the isomers was poor resolution obtained in the infrared
conducted by Escales as follows: Crude TeNCbz spectra of this substance, it was belived to be a
(1 part)(prepd by nitration of carbazole with mixt of decompn and condensation products
fuming HNOa ), was extracted in a Soxhlet for formed in the reaction, together with partially
8hrs using 8PS of glac AcOH. After extracting, nitrated carbazole. Both the middle fraction(mp
the residue which was insol in acid was 253-4°, after recrystn from acet) and the least
separated as a yel pdr which melted with soluble(3rd),fraction(mp 295-6°, after rerystn
decompn ca 274 °(crude rz-TeNCnz). The from AcOH), had N contents close to the calcd
filtrate was allowed to stand until it value for TeNCbz, indicating that they were
deposited rust-brn trysts which began to isomers
melt ca 240° and decomp ca 260 °(crude The least sol fraction was easily
~-TeNCbz). The filtrate was evaported co ca ~th proved to be 1,3,6,8-(or symmetrical) TeNCbz,
vol and cooled. This produced a large deposit of because it was identical with the sample prepd
red-bin, soft plates melting at 264-5° with decompn by heating 3,3’,5,5 ‘-tetranitro-2,2’ -dimethoxy -
(crude y-TeNCbz). The remaining mother liquor wss biphenyl in a sealed tube. The structure of the
slowly poured into ice-water to precipitate a It middle portion was not so easy to determine. It
yel, fine pdr, which decomp on heating to ca was at first believed to be 2,3,6,8-isomer but
200°, without melting (crude 1 8- TeNCbz) “investigation by the method of infrared
On crystn of the crude’a-compd from acet, absorption spectra showed it to be 1,2,6,8
It yel trysts melting at 285-6° were obtained. -TeNCbz. No other isomers were obtained by
When treated with KOH soln the product turned Murphy et al
yel and the color intensified with heating Re/s: l)Beil 20, 441, (168) & [290] 2)
On treating the crude ~-compd with glac C. Graebe & B.vonAdlerskron, Ann 202, 26
AcOH, the bulk of product dissolved leaving as ( 1880) 3)G.L.Ciamician & P. Silber, Gazz 12,
residue some rz-compd. After removing the 277(1882) & JSCI 1, 352(1882) 4) R. Escales,
residue, the filtrate was allowed to stand for Ber 37, 3596(1904) 5)p.Ziersch, Ber 42,
24hrs to deposit a dk-brn amorphous mass with 3800(1909) 6)L.Cassella & Co, Gerp 268173
mp ca 273°(not sharp). warning the @-compd ( 1912) & FrP 4k4538(1913) 7)W.Borsche &
with KOH soln produced a red coloration B. G. B. Scholten, Ber 50, 596, 606 & 608(1917)
Oh treating the crude y-compd with glac 8)H.Raudnitz & H. B5hm, Ber 60 741(1927) 9)
AcOH, only part dissolved, leaving a yel-brn Thorpe 2(1938), 278 10)K.Pfaff, Reichsamt-
pdr, mp ca 275°. The same substance Wirtschaftsausbau ChemBer P B52021, 1183-91
precipitated from AcOH soln after allowing it to ( 1942) & CA 42, 9044-45(1948) ll)K.Pfaff,
stand for 12hrs. This material was claimed to USP 2375382(1945) & CA 40, 426(1946) 12)
be 1,3,6, 8- TeNCbz or Nitrosan. When treated
 c 50

S. Livingston, PACLR 136330( 1951) &PATR These requirements are:

2267(1956) 13)C.H.Brieskorn, ZLebensm a) Primary Material. The carbazole used in the
-Untersuch u -Forsch 93, 292-98(1951) & CA manuf of TeNCbz shall comply with Spec MIL-C
46, 1203(1952) 14)Kirk & Othmer 7( 1951), 437 - 13613 (Ord)(See under Carbazole, Analytical
& 13(1954), 330 15)D. B. Murphy et al, PAMR No Procedures)
MR.22( 1952)( Conf) & JACS 75, 4289-91(1953) b)Moisture in TeNCbz-0.20%, max[when detd by
16)T,Amemiya et al, Coal Tar(Japan) 4, 323-25 heating a 5g at 105~ 5° to const wt(ca 1.5hrs), as
( 1952) & CA 48, 2034( 1954) 17)M.Baer, specified in 4.4]
PATR 1948(1953) 18) P. Tavernier & b)Nitro- nitrogen Content–15.50%, min(when detd
M. Lamouroux, MP 30, 354( 1957) 19)Sax( 1957), by titanous chloride proced, as specified in 4.5.2)
1170 20)PATR 1740, Rev 1(1958), 292-95 c) Sur/ace A lkalinity-O.05% as NH3, max(when
21)PATR 2510( 1958), 197 22)US Spec MIL-T detd by titrating with 0.05NHC1 a 200ml portion of
- 13723 A(Tetranitrocarbazole for Ordnance use) distd w used for rinsing the surface of 10g crys-
talline- TeNCbz, as specified in 4.6)
Tetranitrocarbazole(TeNCbz) Analytical d) Sur/ace Acidity -O.20% as H2S04, max(when
Procedures. TeNCbz used as an ingredient detd as in above process, but using for titration
of explosive, igniter & pyrotechnic compns is 0.05N soln of NaOH, as specified in 4.7)
usually a crude product purified only to e) Total Acidity –O.20~ as H2S04, max(when detd
remove the acidity, mono- dinitrocarbazoles and by titrating with O.OIN NaOH soln the liquid
decompn products formed during nitration. This prepd by heating a 5g sample in 400ml acet and
TeNCbz consists principally of 1, 3,6,8-TeNCbz adding 400ml distd w, as specified in 4.8)
and about 10% of the l,2,6,8-isomer. When f) Total Alkalinity–O.05% as NH3, max(when detd
treated with KOH soln, both isomers turn ted as in above proced, but using for titration O.OIN
and the color is intensified on heating(Refs 1& HC1 soln, as specified in 4.9)
2) g)Melting POint–285 to 300° (when detd as spec-
Compn of TeNCbz prepd at PicArsn by ified in 4. 10)
Livingston(Ref 3) was established by detg Note: The app and proced are similar to those
total nitrogen content(using micro-Kjeldahl given in Vol l,pp A612-R & A613-L
app)~ nirro-nitrogen content(by tltanous chloride h) Acetone Insoluble Material-O. 15%, max(when
method) and carbon-hydrogen content(by micro detd by weighing a residue remaining after treat-
-combustion method) ing a 5g sample with two 200 ml portions of hot
For detn of purity of TeNCbz, Kaye(Ref acet, as specified in 4.11)
4) developed at PicArsn a method of titration, i) Granulation-a min of 100% shall pass thru a No
using dimethyl formamide as a medium and a 100 sieve, when detd as specified in 4.12
soln Na methoxide as the titrant. As the end Note: Info about sieves is given in Table 1,p
point could not be detd visually(using azo A674, Vol 1 of this Encyclopedia
violet as indicator) due to the darkening of the Re/s: l)R.Escales, Ber 37, 3597(1904) 2)W.Fischer,
TeNCbz sample in the vicinity of its end ZAnalChem 131, 192- 8(1950) & CA 4!5, 803(1951)
point, a potentiometric procedure was used, 3)S.Livingston, PicArsnChemLabRept 136330
employing antimony and calomel electrodes. (195 1) 4)S.M.Kaye, pATR 1937(1953)
It was found that production grade TeNCbz
gave purity values which were consistently Carbazotine(Fr). Same as Carboazotine
slightly in excess of 100%(such as 100.15%).
This anomaly may be due to traces of acidic Carbazotique, Acide(Fr). Picric Acid
impurities retained in the compd after its
synthesis and purification. These acidic compds Carbene. /)Same as Cupr’ene, (C,, -1 ~H, ~)x, a
neutralize part of the Na methoxide titrant, yel-bm polymerization product made by heating
thus giving a higher reading in titration. acetylene in the presence of Cu(Ref 1) 2)A posi-
Purity of production grade material after its tive or negative ion involving two- valent carbon
purification by recrtsg twice ftom acetone was and paired electrons as in H2C:, R2C: or R2C++.
ca 99.9% These ions are different from methylene free
Requirements of US Armed Forces for TeNC bz radicals in that the latter have unpaired electrons.
used for militam purposes are covered by Specif- Carbenes have only transitory existence and are
ication MIL-T-137 23A, superseding PA-PD-639. difficult or impossible to collect as such, but
 c 51

have important functions as intermediates in Ordn 36, 151- 3(1951) 3)W.H.B.Smi*,

them reactions (Ref 3). See also Ref 2 3) “The NRA Book of Small Arms” The Stackpole
Constituent of bitumen, insol in CC14 or chlf but Co, Harrisburg, Pa, v2(1952), 30 & 378 4)
SOI in CS2(Refs 1 & 4). Carbenes have been used W. Y. Carmen, ‘tA History of Firearms”,
as ingredients of some coml expls, See also StMartin’s Press, NY(1955), 125-30 5)
bitumens under AsphaIt, Voi 1,p A496R Glossary of Ord(1959)55-.6 6) W. H. B. Smith,
Re/s: l)Hackh’s(1944), 166& 241 2)P.S.Skell & “Small Arms of the World”, The Stackpole Co,
R. C. Woolworth, JACS 78, 4496- 7(1956) & CA 50, Harrisburg,Pa(1960), 87- 92& 628-31
16656(1 956) (Structure of carbene, CHZ) 3)Cond-
Chem Dict( 1961), 215 4)Merriam- Webster’s Carbite. A dynamite, proposed by Dautriche
(1961), 335 (Ref 1) and approved in 1907 by the Commission
des Substances Explosives, consisted of:
Carbethoxy. See Carboethoxy NG 25, KN03 34, wheat flour or starch 38.5,
Ba(N03)21, powd bark 1 & Na2CO~ 0.5%
Carbides, Carbonides or Carburets. Binary Re/s: l)M.Dautriche, MP 14, 177(1906- 7) &
compods of carbon and a metal. Some carbides CA 3, 2053(1909) 2)Marshall, Dict(1920), 18
dec readily in w to give acetylene 3)CondChemDict( 1942), 288 (not found in
(Li4C,K4C,CaC2 ,SrC2 or BaC2 ); others form later editions)
methane(A12C or B2C), or hydrogen &
methane(MgC2 ,Mn3C or Cr9C), or a mixt of “Carbitol”. A trademark of the Union Carbide
acetylene, hydrogen & methane (rare earth Corp for mono- and dialkyl ethers of
carbides); while those of the rare metals diethylene glycol & their derivs
Re/s.’ l)Hackh’s(1944), 166 2)Sax(1957), 435
( Thcz or U2Ca ) form solid, liq or gaseous
hydrocarbons. Carbides such as Sic or 3)CondChemDict( 1961), 216
TixCy are extremely stable(Ref 1)
See Acetylides and Carbides, Vol 1, “Carbitol” Solvent or Diethylene Glycol
p A69ff and Ref 2 Monoethyl Ether (called Di3i’thylenglykol
Refs: l)Hackh’s( 1944), 166 2)M.Delib6r.4, -monoiithyl~ther in Ger),
JFourElec 45, 344- 5(1936)& CA 31, C2H~’0’CH2*CH2”O”CH2 ”CH2”OH ; mw 134,17;
865(1937 )( Explosions in iron carbide drums) COI hygr liq, having a mild pleasant odor,
bp 195-.202°, flash p 205 °F(0C), d 1.027 at
Carbine(Karabiner in Ger; Carabine in Fr; 20°, vap d 4.62, no 1.425 at 25°; other props &
Karabin in Rus; Carabina in Ital and Carabina methods of prepn are given in the Refs. It is
in Span). A short, light weight rifle formerly used as a SOIV for dyes, NC, resins & other
used by cavalry and mounted infantry, but in materials
recent years also used by other troops. The Rets.’ l)Beil 1, [520] & {2096} 2)Hackh’s
term ~‘carbine ‘‘ is probably derived from (1944), 166 3)Sax (1957), 435 4)CondChem
“carabineros”, Spanish mounted troops which Diet (1961), 376
were equipped, beginning the middle of 16rh
century, with a short light wt firearm which Carboazotine or Cahuecit. One of the early
could be fired directly from a horse. This safety blasting expls invented in the 1870’s
weapon was called petronel or poitrinale by R. Cahuc. Its compn in Englimd was
(See under Bullets, Historical and also KN03 64, suIfur 12, lampblack or soot 7 &
Refs 3 & 4) bark or wood pulp 1.7%; in France (called
Carbines used by the US Armed Forces Poudre de mine de Soulages ou de Sfiret6)
during WWII were either semiautomatic or NsN03 50 to 60, sulfur 13 to 16, spent tan
automatic. For their description, see Refs bark 14 to 16, soot 9 to 18 & Fe sulfate 4 to
3&6 5%; and in Germany (called Cahkit) KN03 or
The story of how Amer industry helped NsN03 70, suIfur 12, lampbIack or soot 8 &
to develop modern carbines is told by Carlen bark or woodpulp 10%, The ingredients were
(Ref 2) incorporated with a considerable amt of water,
Refs: l)Anofl, “Small Arms Mat6riel”, which afterwards was evaporated. This expl
TM 9- 2200(1949), 15 2)C01 L .A.Carlen, was considered comparatively mild
 C 52

Refs: l)Cundill (1889); Fr translation MP 6, 1 ,p A192- R

101-2(1893) 2)Gody (1907), 171 3)Marshall
1(1917), 89 and “Dictionary of Explosives” N- Carboethoxy-1 - amino- 2- ethanol; N-(2
(1920), 16-7 4)Ullmann, vol 4(1929), 780 -Ethanol)- urethane; N- (2- Hydroxyethane)
5)Pepin Lehalleur( 1935), 287 6) Thorpe - urethane or 2-. H ydroxy- 2- urethane- ethane,
( 1940), 463 6)CondChemDict ( 1942), 288(not HO”CH2”CH2”NH(COOC2 H5), and its
found in later editions) 7)PATR 2510 (1958), nitrated deriv, 02NO”CH2“CH2N(N02) -
p Ger 23 (COOC2H5 ), serve as intermediate compds in
the prepn of NENA described under
N(or 4)- Carbobutoxy- morpholine(called Aminoethanol and Derivatives, Vol 1,p A201- L
Butylur6thane de la morpholine or Morpholine
ur~thane butylique in Fr), N-Carboethoxy-2-amino-2-methyl-l-propanol;
cH2”’332\ N-Carboethoxy-2-amino-2-methyl-1-hydroxy-
~/
N. COOC4H9; mw 187.33, propane or 1- Hydroxy - 2,2- dimethyl - 2- urethane
\
CH2”CH2’ -ethanet ~H’COOC2H5
N 7.48%; Iiq, fr p -4°, bp 252-2.5°; was H3C–C–CH20H , and its nitrated
prepd by the action of butylchIoroformate on an %,
~n ,
aq soln of morpholine(Ref 2). It was tried in ~(N02)?OOC2H~
France as a possible substitute for deriv, H3C-$-CH2(ON02) , serve as
centrality in solventless, smokeless proplnts CH3
(poudres SD)(Ref 3). The props .of proplnts intermediate compds in the prepn of 2
prepd with this compd resembled those contg - Nitramino- Z-methyl-1 -propanol Nitrate
N(or 4)- carboethoxy - morpholine (qv) described under Aminomethylpropanols and
Re/s: l) Beil–not found 2)L.M+dard,BullFr Derivatives, VOl 1,P A233-R
[51 3, 1343(1936)& CA 30, 7577-8(1936)
3)R.Dalbert & H. Ficheroulle, MP 30, N- Carboethoxy-l - amino-2- propanol; N-(2
283- 300(1948) - Propanol)- urethane; N- (2- Hydroxypropane)
-urethane or 2- Hydroxy - (1 - urethane)- propane,
Carbodynamites. Explosives patented in 1886 CH2”CH(OH)CH3
by Borland & Reid of GtBr. These compns I ,
and its nitrated deriv,
differed from ordinary dynamite in that NG was NHCOOC2H5
absorbed in cork charcoal instead of
CH2“CH(ON02)CH3
kieselguhr.
following:
Two compns consisted of the
No 1 NG 90 & cork charcoal 10~; No 2
I , serve as intermediate
N(N02)COOC2H5
NG 71,4, KN03 20 & cork charcoal 8.6%. As
compds in the prepn of Nitraminopropanol
stabilizers Amm or Na carbonate up to 1.57. of
Nitrate described under Aminopropanols and
total wt of expl was sometimes added. There
Derivatives, VOI 1,p A253- L
existed also a variety of carbodynamites contg
up to 207~ of water; these expls were
N-Carboethoxy - furfurine or Urethane
comparatively safe to handle
- furfurine(called Ethylurdthane de la furfurine
Re/.s: l)Daniel (1902), 108-9 2) Barnett
or Furfurine ur~thane ~thylique in Fr and
( 1919), 97 3)Marshall, Dict(1920), 18 3)
Furfurin- N- carbonsaureathy lester in Ger),
CondChemDict(1942), 288(not found in
later editions) 0C6H3’HC
‘N<C .C H O
; mw
0CeH3”HC–N(COOC2H# 4 3
N- Carboethoxy-2- amino-l - butanol; N-(1
-Butanol)- urethane; N-.(1 - Hydroxybutane) 340.32, N 8.23%; prisms (from ale), mp 120-4°;
-urethane or 1- Hydroxy - 2-urethane- butane, insol in eth; diffc sol in w; was prepd by reacting
, and its nitrated deriv, furfurine with ethyl chloroformate in abs eth
CH3”CH2”$H”CH2”OH
NH”C00C2H~ (Refs 1 & 2). It was tried in France as a
possible substitute for centrality in solventless,
CH3“CH2”<H”CH2”ON02, serve as intermediate
smokeless proplnts (poudres SD), but proplnts
N(N02)”COOC2H5
prepd with it were unsatisfactory (Ref 3)
compds in the prepn of 2- Nitramino- 1- butanol
Nitrate listed under 2- Amino- 1- butanol, Vol Re/s: l)Beil 27, 764 2) R. Bahrmann,
 c 53

J PraktChem 27, 318(1883) 3)R.Dalbert & - Carb~thoxy - phenyltriazen or 4-.Triazeno

H. Ficheroulle, MP 30, 283-300(1948) - benzoes~ureathylester in Ger),
H2N3C6H4”COOC2H5; mw 193.20, N 21.75%;
N(or 4).. Carboethoxy: morphol ine or Urethane granules or ndls (from eth + gasoline), mp 68°
- morpholine[called Ethylur6thane de la (dec); was prepd by reduction of 4- azidobenzoic
morpholine or Morpholine ur6thane 6thylique in acid ethyl ester by SnC12 soln in eth. This
Fr and Morpholin -carbonsaure - (4)- ~thylester compd dec on long storage even below RT, at
in Ger], ,CH2”CH2\ higher temps it dec explosively; dec in alc or dil
o\ N“COOC2H5; mw 159i18, acids; an erhereal soln with fortdaldehyde
CH2“CH2~ condenses to form a compd decomg at 48°; it
N 8.80%; oil, fr p 2.5°, bp 220-1° at 746mm combines with benzaldehyde, but the compd is
(Refs 1 & 2), bp 223° at 764mm (Ref 3) & bp too unstable to isolate(Refs 1 & 2)
251° (Ref 4); was prepd by the action of It forms salts, some of which are expl:
ethylchloroformate on an aq soln of Copper salt, CUC 9 H 10 N 3 O 2 J golden- Yel
morpholine (Refs 1,2 & 3). It was tried in lfts(from chlf), dec at 130° and expl over a
France as a possible substitute for centrality in flame; Tin salt, expl on heating
solventIess, smokeless proplnts (Ref 4). A Re/s: l)Beil 16 (410) 2)0. Dimroth &
compn (contg NC, NG, carboethoxymorpholine & K. Pfister, Ber 43, 2763- 64(1910); JCS 98 I,
cenrralite) was easy to roll or extrude but the 905-6(1910) &CA 5, 486(1911)
resulting proplnt was more brittle than when
prepd with centrality alone. The stability of Carbogelatin. A Brit expl consisting of NG
proplnts made with carboethoxy - morpholine was (gelatinized with NC) 38.5, K or Na nitrate
fairly satisfactory even at temps up to 90° 49.5, woodmeal with charcoal 10.5 & MgC03
Re/s: l)Beil 27, 7 2 )L.Knorr, Ann 301, 1.5%
7(1898) 3)L.M6dard, Bu11F~5] 3, 1343(1936) & Ref.’ Daniel( 1902), 109
CA 30, 7577- 8(1936) 4) R. Dalbert & H. Ficheroulle,
MP 30, 283- 300(1948) Carbohydrates. A class of compds of C,H & O in
which H & O are in the same proprotion as in
Carboethoxynitramine. See Nitrocarbamic Acid H20. Also org compds which are synthesized by
Ethyl Ester under Carbamic Acid and plants. A more rigorous definition is that
Deriva~ives carbohydrates are aldehyde alcohols, ketone
alcohols or compds that on hydrolysis produce
Carboethoxynitrosamine. See Nitrocarbamic aldehyde or ketone alcohols. Examples of
Acid Ethyl Ester under Carbamic Acid and carbohydrates are the tryst, sol, sweet, low
Derivatives molecular wt sugars; and the amor, tasteless,
relatively insol high molecular wt starches &
[I(or N’)- Carboethoxyphenyl -lll(or N) cellulose. Specific examples are sucrose,
- carbani1ino]- triazene or [[(or N’)- Carboethoxy. C12H2201 ,, and starch, (C6H, 005)X (Refs 2 &
phenyl - III(or N). phenylcarbamyl]. triazene 12)
{called l(oder 3)-[4- Carb5thoxy-phenyl] -triazen Some reactions relating to carbohydrates
- (1)- carbons~ure- (3 oder 1)- anilid or N’ were studied by Ashford et al(Ref 3). The
-[4- Carbathoxy- benzoldiazo] - N- phenyl nitration of carbohydrates & their stability have
- harnstoff, in Ger\, been studied by many investigators, such as
C6Hs”NH”C0’NH”N:NC6 H4’COO”C2H5 ; mw Ashford et al (Ref 4), Wolform(Ref 11) and many
312.32, N 17.94%; COI pltlts (from aIc), mP 135° others. See also Evan’s (Ref 1), Dorge(Ref 5)!
(dec); readily sol in chlf, eth or hot ale; insol in K & O(Ref 6), Vollmert(Ref 7), Ott(Ref 8)
w; was prepd from the reaction of 4-triazeno Wolfrom & Tipson(Ref 9) and Honeyman (Ref .10)
-benzoic acid ethyl ester and phenylisocyanate Refs: l)W.Q.Evans, ChemRevs 31,
in eth (Refs 1 & 2) 537-60( 1941)(Some aspects of carbohydrate
Refs: l)Beil 16, (411) 2)0. Dimroth & chemistry) 2)Hackh’s(1944), 217 3)
K. Pfister, Ber 43, 2764(1910)& JCS 98 I, W. R. Ashford et al, CanJRes 24B, 238-45
904-5(1910) ( 1946)(Stabilizing action of ethanol on starch
nitrate); Ibid, 249, 246-.5 3( 1946)( Props of
4- Carboethoxy - phenyltriazene( called 4 fractionated nitrates of cornstarch) 4)
 C54

W.R.Ashford et al, Can]Res 256, 151-54 given in Beil and in Ref 2

( 1947)( Effect of hot alkali solns on the nitrates Refs: l)Beil 3, 121, [96] & { 232} 2) L. F. Au~ieth
of starch, amylose & amylopectin); Ibid, 25B, et al, Inorg Synth 4(1953), 36
155-” 58(1947 )( Stability of maltose &
cellobiose octanitrates) 5)C.Dor6e, t ‘The Carbohydrazide-N-carboxyamide, C2H7Ng02.
Methods of Cellulose Chemistry”, Chapman & See S.Helf, PATR 1752( 1949)( Conf)
Hall, London(1947), 543 pp 6)Kirk &
Othmer, 3(1949), 342ff 7)B.Vollmert, MakrChem Carbohydrazide-N,N-dicorbamoyl(called 1.5
6, 78-8 4(1951) & CA 45, 9487(1951) 8) EsOtt, - Dicarbamoyl- carbohydrazid or Carbonyl - bis
“Cellulose and Cellulose Derivatives”, Vol 5 - semicarbazid. in Ger),
of High Polymer Series, Interscience, NY, Three CO(NH’NH”CO”NH2)2; mw 176.14, N 47.72%; CO1
Parts(1954-.55) 9)M.L.Wolfrom & R. S. Tipson, trysts (from w),. mp 225- 32°(dec); SO1 in hot W!
“ ‘Advances in Carbohydrate Chemistry”, diffc -sol in cold w; in sol dil acids, ale, eth or
Academic Press, NY, Vol 11(1956) 10) other org SOIVS; when heated with w in a test
J .Honeyman, Edit, “Recent Advances in the tube at 1500, it yields carbohydrazide & 4
Chemistry of Cellulose and Starch”, - aminourazole. other props & methods of prepn
Interscience, NY(1959) 1 I)M.L.Wolfrom, are given in Beil and in Ref 2
“Study of Nitrated Carbohydrates”, Ohio State Re/s: l)Beil 3,122, [97] & {232} 2)
Univ Quart Prog Repts No 1, 2 & 3(Feb 1959 L. F. Audrieth & P. H.Mohr, Inorg Synth 4(1953), 38
- Ott 1959)(Proj No 2317, Contract NO DA-33
- 0190RD- 2923 12)CondChemDict( 1961), 217 Carbohydrazide - N,N’ - dicarboxyamide,
C3HSN603 . See S. Helf, ‘PATR 1752( 1949)(Conf)
Carbohydrazide; sym or N,N’-Diaminourea
(called Carbohydrazid; Kohlensauredihy drazid or Carbomethoxynitramine. See Nitrocarbamic Acid
N, N’- Diamino- harnstoff in Ger), Methyl Ester under Carbamic Acid and Derivatives
CO(NH”NH2)2; mw 90.09, N 62.20%; CO1 ndls
(from dil ale), mp 152- 54°; d 1.616 at 20°; Carbomethoxynitrosamine. See Nitrosocarbamic
insol in eth, benz or chlf; other props & various Acid Methyl Ester under Carbamic Acid and
methods of prepn are given in Beil(Ref l)(See Derivatives
also Ref 2)
Carbohydrazide is not an expl, but in the CARBON(Carbone in Fr, Carbon or Kohlenstoff
presence of nitrous acid is converted into the in Ger, Carbonio in Ital, Carbono in Port,
highly expl Carboayl Azide, CO(N3)2(See Vol 1, Ugol’ or Karbon in Rus & Cark”n in Sp), C, at wt
p A528- L) 12.01; blk trysts or powd, mp 3652°-3697°
It is incompatible with NC as the film (sublimes), bp 4200° (approx); d 1.8- 2.1 (amor),
prepd from a mixt of NC & carbohydrazide gave 2.25 (graphite), 3.5 I (diamond), vap press lmm
1 ICC in 16hrs in the 90° Vac Stab Test, and at 3586°; in the form of graphite it can cause
exploded after 8hrs heating in the 1200 Heat dust irritation to the eyes, in the form of soot it
Test(Ref 3) can cause conjunctivitis and other inflammation
Re/s: l)Beil 3, 121, (57), [96] & {231} of the eyelids & cornea (Ref 45)
Univ of Illinois, Urbana, Ill, 2) L, F. Audrieth & Carbon occurs free in nature and has been
E. B. Mohr, Progress Rept IV, Contract No W-11 known since ancient times. It is the basic
-.022. .ORD - 11329(1949) 3)J .P .Picard & element around which all organic life revolves.
W.P .Morton, PicArsn data(May 1955) It exists in two tryst forms: diamond 6
graphite and in various(’ ‘amorphous”) forms, such
Carbohydrazide-N-carbamoyl(called 1 as carbonblacks (acetylyne black, lampblack,
- Carbamoyl- carbohydrazid or Hydrazin- N.N’ etc) and charcoal. Soot & coke are impure
-dicarbos;ure-amid-hy drazid in Ger), amorphous carbon
H2N”NH’CO”NHSNH”CO* NH2; mw 133.12, N Diamond is one of the hardest known
52.61%; crysts(from boiling w), mp 228°(dec); substances and because of its props is used to
sol in dil mineral acids; sol in KOH soln with cut glass & minerals, in drilling tools and as
decompn; insol in w, alc or other org SOIVS; bearings in watches t% other precision
when heated at 226° it cyclizes, in part, to form instruments. Graphite is used in pencils, in
urazine. Other props & methods of prepn are refractory crucibles and in electrotyping. The
 c 55

use of graphite in expls & propInts is described ballistic regularity. Streijffert (Ref 18) prepd
below. ‘tAmorphous” carbon or carbon blacks, expls by treating activated carbon with a liq
of which there are several kinds, are made by such as NG or Te~Me, removing the surplus liq,
burning org substances in an insufficient t resting the C with HNO$ and neutralizing the
supply of air. This important group of industrial acid with NH3. The resulting mixt contd the
carbons are used in the rubber tire industry, in NH4 salt dispersed in the pores of C. The
plastic compounding, as thermal insulators, and activated C used for SOIV recovery during wwII
as black pigment in ink & paint industries. It is was also used in some US smokeless
an essential component of some metals such as proplnts(Ref 11)
cast tion & steel. A special form of carbon one of Hercules’ Bullseye Propellants
called “Active” or “Activated” ~ prepd by (qv) manufd during WWII contd some carbon
carbonization of carbon- containing materials black; the Hercules E J Propellant, called
such as wood, sawdust, peat, lignite etc, is used ‘{Pigseye Powder”, ‘contd KC104 56,
for its absorptive props in removing odors, NC 21, NG 13, Et cent 1.0 & carbon 9% (Ref 55).
tastes, colors etc from liquids & gases Carbon has been used in Ammonals (See Vol 1,
Explosibility of Carbon Dust G Its Use in pp A289, A290 & A299- L) in Black powder (qv)
Explosives. Carbon black, presumably produced and in a large number of other expl compns, such
by incomplete combustion of natural gas, was as Blasting Explosives, including Liquid Air &
easily ignited, and it propagated a flame readily Liquid Oxygen Explosives (Oxyliquits). DeMent
when the testing gallery at the US But Mines (Ref 54) used C in smoke compns
Experiment Station was loaded with a concn of Coating smokeless proplnts with graphite
12g dust lft3 (Ref 2). Researches on the usually achieve the following purposes: a)aids
explosibility of C dust in relation to initial in removal of static electricity b)acts as burning
ignition & conditions of dispersion are deterrant c)acts as a lubricant and d)prevents
abstracted by Langhans (Ref 28). Sax (Ref 45) caking or cohesion of the proplnt grains
reports that activated C may spontaneously Crawford (Ref 17) found that unstable
ignite on heating and explodes when its dust is burning in double-base proplnts can be overcome
exposed to flame. Elliott & Brown (Ref 13) by incorporating in the powder opaque C black or,
investigated the expln hazards of mixts of as Hickmm (Ref 24) found,lampblack for
perchloric acid & carbon, carbonaceous material preventing self- ignition by radiation. See also
and other org materials. The expIn of C with Cannonite
Iiq air to give CO (Ref 6), and other processes or Some expl compns, contg C and examined
expln hazards involving C are described in the at PicArsn included: Illuminating Cornposition,
literature. See Refs given below, eg Reg 51 Sr(N03)2 54, Mg 33, PVC 10, C 3 & Ca stearate
Capt Monni (Ref 1) reported in 1906 that 1%; Squib, NC, (lacquer) 51, KCIOa 44 & C 5%;
the addn of C to one of ‘the “ballistites” Flare, Mg 44, NaC104 35, Na202 4,
lowered the temp of combustion, increased the phenolformaldehyde resin 15 & graphite 2%;
vol of gases and decreased the chamber press Flare First Fire, KN03 64, C 17, S 14, &
per kg of propellant; and carbon decreased the Sb2S9 5%; Relay Charge, KN03 64, C 14, S 16 &
propellants’ rate of burning. Gun erosion AI 6%; and a Blasting Charge, KC103 46,
caused by such proplnts was less than that S 6 & binder(rosin) 42%
produced by ,straight ballistite. me C contg See also Charcoal, Coal & other
proplnts were claimed to be easy to make, carbonaceous materials
resistant COvariations in temp & humidity, R efs: l)capt (?) Monni, SS 1, 305- 8(1906) &
constant in ballistic action and they did not CA 2, 2993(1908) 2) Anon, ChemEngrg 27,
leave any residue in guns. The chemical factors 123- 24(1919) & CA 13, 2130(1919) 3)Mellor ~
affecting proplnt ignition, in addn to the presence (1924), 710ff 4)A.Godel, Chim & Ind 29, 3T
of free O & C, are discussed in a recent article -17 T( 1933)( Activated carbon & its ind
by Cook (Ref 40). Also the factors influencing applications) 5)Thorpe 1( 1937), 140 & 2
the incendivity of permissible expls (~+ (1938), 308-19 6)L’Air Liquide, FrP 861602
carbonaceous materials) are reported by Hanna et ( 1941) & CA 42, 6500(1948) 7)Hackh’s (1944),
al (Ref 53). Pring (Ref 21) found that the 167 S)T.D.Johnson, Jr & R. G. Woodbridge, Jr,
incorporation of small amts of C’ black in NGu USP 2342585( 1944) & CA 38, 4806(1944)
proplnts assisted in ignition & improved their (Purifying graphite after contamination by use in
 C 56

glazing smokeless proplnts) 9) C. L. Mantell, black from natural gas; a tech & economic
t ‘Industrial Carbon”, Van Nostrand, NY( 1946) discussion) 35) Metallgesellschaft A- G, BritP
10)H. L. Riley, Quart Revs l,No 1,59-72(1947) 704810(1954) & CA 48, 9660( 1954) (Active
(A review on amorphous carbon & graphite) 11) carbons) 36) J. H. Schroeder, JARS 23, 25-7
Anon, Chem Engrg 54, 98-99( Jan 1947) 12) (1953) & CA 48, 6126( 1954) (Performance Of
Kirk & Othmer 2(1948), 881; 3(1949), 34ff & stoichiometric carbon= oxygen
First Supplement (1957), 130–44 13) M. A. Elliott propellent system) 37) A. Humann, “Der Graphit
& F. W.Brown, US Bur Mines Rept Invest 4169 Eigenschaften und Verwendungsmoglichkeiten in
( 1948), 17pp & CA 42, 2431- 32(1948) 14) Industrie und Kraftfahrwesen”, Verlag Tech,
W. M. Gaylord, Chem Engrg 55, No 3, 225(1948) Berlin( 1953) 38)L.J .Venuto, P ainthianuf 24,
(Carbon & graphite) 15) B. L. CrawfordZ USP 197-202 & 227-34(1954) & CA 48, 11078(1954)
2440327(1948) & CA 42, 5230(1948) 16) (Carbon blacks for protective coatings; manuf &’
J. Basiak & T.Niewiadomski, PrzChem 4, 304-7 general props and selection of materials) 39)
( 1948)( Review of methods of producing carbon M.Steinschlaeger,USP 2694621( 1954) (Carbon
blacks, their props & uses) 17)B.L.Crawford, black) 40)M.A.Cook, AIChEJournal, 1, 391-400
USP 2440327( 1948) & CA 42, 5230( 1948) 18) (1955) & CA 50, 1316-18(1956) 41)
P .W.Streijffert, USP 2485889( 1949) & CA 44, Deutsche Gold- u Silber-Scheideanstalt, vorm
2246(1950) 19)Partington (1950), 593ff 20) Roessler, BritP 738068( 1955) & CA 50, 9723
J. W. Hassler, ‘ ‘Active Carbon”, ChemPub CO, NY ( 1956)( Improved carbon biack manuf) 42)Gmelin;
(1951), 390PP 21) J. N.pring, USp 2557463 Syst Nr 59(1955) & (1959) , 64ff 43)J.Q.W’ood,
(195 1) & CA 45, 9863(1951) 22) Anon, Chem USP 2735828(1956) & CA 50, 9724(1956)
Engrg 58, 176- 79(July 1951)( Carbon black) 23) (Recovery of carbon) 44)H.A.Braendle, USP
E. Beri, USP 2567468(1951) & CA 46, 1236 2735753(1956) & CA 50, 9724( 1956) (Improved
( 1952)( prepn of activated carbon) 24) carbon black manuf) 45)Sax(1957), 245, 436
C. N. Hickman, USP 2574479(1951) & CA 46, 46) F. C. Stehling et al, “Sixth Symposium on
1259(1952) 24a)N.A.Pirozhkov, “Proizvodstvo Combustion”, Reinhold, NY (1957), 547-54
Sazhi” (Production of Soot’ ‘), Gosudarst Nauch (Carbon formation from acetylene) 46a)Kirk &
- Tekh Izdatel’stvo Legkoi Prom, MOSCOW(195 1), Othmer, First Suppl Volume( 1957), 130-43
l18pp 25)C.A.Stokes & H. Friedenstein, (Carbon biack) 47)Anon, “Industrial Carbon and
Northeastern Wood Utilization Council Bull, Graphite”, SocChemInd, London (1958 )( Papers
NO 37, 7-19(1952) & CA 46, 420 fX1952)(ProPs of read at the conference held in London 24 to 26
coml charcoals in relation to industrial use) 26) Sept 1957 with discussion that followed) 48)
J .W.Hassler, Northeastern Wood Utilization I. Asimov, ‘The World of Carbon”, Abelard
Council Bull, No 37, 93- 101(1952) & CA 46, - Schumann, NY(1958) 49)ASTM Standards
4200( 195 2)(Review of methods for producing Including Tentative Part 9 Plastics,
active carbon & of its industrial applications) Electrical Insulation, Rubber, Carbon Black”,
27)Anon, Chem Engrg 59, NO 3, 206- 9(1952) & Am SoC Testing Materials, Philadelphia(1958);
CA 46, 4200( 1952) (Carbon recovery from black Supplement (1959) 50) Anon, ‘ ‘The Industrial
ash) 28)Dr (?). Langhans,SS 1952, 213-14 29) Graphite Engineering Handbook”, Natl Carbon
R. H.Savage, USP 2601953( 1952) & CA 47, Co, NY(1959) 51)A.K. Galwey & P. W. M. Jacobs,
850( 1953) (Graphite carbon) 30)A. E. Fr@ss, Usp TrFaradSoc 56, 581- 90(1960) & CA 54, 18045
2619410(1952) & CA 47, 850(1953 )( Carbon (1960) [Below 240° various mixts of NH4C104 &
black produced by expl conversion of methane C (sugar charcoal) undergo isothermal decompn;
- oxygen mixts) 31)ChemischeWerkeHtils, above 260° the reaction accelerates rapidly &
firitP 685160(1952) & CA 47, 5100(1953) results in a mild expln] 52) R. M. Krupka &
(Carbonization of fuels) 32)Van NostraIId- D. E. Tay16r, Corrosion 16, 385t-89t(1960) &
ChemDict (1953), 128 32a) V. P.Zuev & CA 54, 19384( 1960)( Behavior of graphite in
V. V. Mikhailov, ~tproizvodstvo Sazhi” rockets on reentry) 53)N. E.H anna et al,
(Production of Soot”), Gosudarst Nauch- Tekh US But Mines RI 5867(1961) 54)J DeMent,
Izdatel’stvoKhimLit, MOSCOW(1953), 198PP USP 2995526( 1961),PP 25-7 55)G.D.Clift,
33)H.L.Ammann, USP 2658821(1953) ~ CA 48> Private communication (1962) 56) USSpec MIL
1658( 1954)( Apparatus for producing carbon black - A- 3850( Acetylene Black); MIL- C- 20613
by expln process) 34)G. W. Govier et al, Can- (Activated carbon, granular); MIL.C- 50@ (1)
Chem Processing 38, No 5, 67- 70(1954 )( Carbon (Activated carbon, powered); and JAN- C- 306

.——
 c 57

( I)(Carbon black, dry for use in expls) been asborsed by KOH. If there is turbidity, roll
Addnl Re/: L. Pauling et al, OSRD Rept 3783 the bomb for an addnl 5mins and then test again
(1944)( Ballistites of approx compn NC 52, NG 43, Allow all th~ gas to escape into the
K nitrate 1.5, DEtPh 3.o & DPhA 0.5% atmosphere. Remove the cover and wash it with
exhibited better thermal stability with added distd w into a 25ml volumetric flask with the aid
carbon black, ca O. I%, than with Nigrosine dye. of a funnel. Transfer (quantitatively) the
These substances serve as opacifying agents) contents of the bomb into the same flask and
fill it with w to mark. After mixing the contents,
Carbon Analytical Procedures. When total carbon pipet a 50ml aliquot into a tall beaker and
in nitrogen contg compds or compds (such as titrate with std HC1 soln using successively two
expls or proplnts) is detd by combustion in a indicators, first phpht and then methyl orange
glass tube contg CUO (method of Dumas), there Calculation. If reading with phpht indicator is
is always the possibility that oxidation of C to n and with methyl orange n’, then
C02 will accelerate to such an extent that the %C= [6.005 (n’-n)f-26p] /P, where f is
sample will expl or defgr (thus destroying the normality of HC1 (usually 0.5), p the wt of NC
combustion tube) even when the sample is used for igniting the sample and P the wt of
previously mixed with materials retarding sample taken
combustion such as benzophenone proposed by Free carbon (such as carbon black or
J ovinet et al, (Ref 8). Modifications of method of graphite) in colloidal proplnts can be detd by
Dumas proposed by Boivin (Ref 6) or by several methods. The gravimetric method
Courtecuisse (Ref 9) are not always applicable described in Ref 14 is essentially as follows
to expls or proplnts Procedure: a) Place a 5g finely divided sample
Less dangerous is the method of combustion in a 4oOmI beaker, add 75ml of coned nitric acid,
in a closed bomb (calorimetric bomb) contg a ACS grade, and cover with a watch glass b)Heat
large amt of compressed oxygen, followed by on the steam bath until reaction starts. Remove
analysis of resulting gas for the amt of C02 from the bath and wait until the reaction subsides
formed on combustion of C. This method was c) Replace the beaker on the bath and allow the
first proposed by Berthelot (Ref 1) and modified mixt to digest for lhr d) Remove from the bath,
by Hempel (Ref 2). Badoche (Ref 3) and chill in an ice box, add 75ml distd w, and allow
BurIot (Ref 4) investigated the method and to stand until the major part of carbon black has
found it to be satisfactory settled out e) Filter the supernatent liquid very
In both Berthelot’s method and its slowly thru the tared crucible with asbestos
modifications, the gases produced on combustion filter, using gentle suction f) Transfer
or expln are analyzed after they are removed quantitatively the residue in the beaker to crucible
from the bomb. Thomas (Ref 10) found that it is and rinse the beaker and contents of the crucible
simpler to analyze the gases directly in the with distd w until most of the acid is removed
bomb without transferring them to another vessel. g)Continue gentle suction for 5mins and
This method is essentially as follows: discard the filtrate h)Dry the crucible in the oven
Procedure: Place on the bottom of a calorimetric for 30mins at 100° and cool it to RT without
bomb of 500ml capacity, 50ml of 20% KOH and placing in a desiccator i)Without weighing the
suspend a sample in the form of a compressed crucible, rinse its contents with solvent contg
tablet (ca 0.8g weighed to l/10th mg), together I VOI of acet & 2 VOIS of ether (using gentle
with an igniter consisting of a bridge wire suction) until the filtrate becomes colorless j)
enclosed in NC, previously weighed. Close the continue to aspirate gently until the disappearance
bomb and introduce compressed oxygen until the of odor of solvent, then dry the crucible in an
pressure inside the bomb reaches 25kg/cm2. oven at 125~5° for 30mins, cool in a desiccator and
Ignite the sample by switching the current on in weigh k) Place the crucible in a muffle furnace
the same manner as when detg the heat of at 600-650° and leave until all carbonaceous
combustion. After cooling the bomb, wipe it off material has been burned I) Remove the crucible
and roll on a flat surface for 5mins to insure that from the furnace, cool in a desiccator to RT, and
all CO* is absorbed by KOH. Open the release weigh m)Det the loss in wt of the crucible after
valve slightly and allow some of the gas to ignition and talc this loss as the percentage of
bubble thru a Ba hydroxide soln. If no turbidity C in the proplnt on a volatiles - free basis
appears,it means that all C02 in the bomb has Donovan (Ref 8a), did not think that the
 C 58

gravimetric method using nitric acid was Detn of charcoal in BkPdr by methods
accurate enough and he proposed a photometric used at Bofors Labs (Sweden) and at PicArsn
method, in which the absorption of light by solns Lab (Dover, NJ) is described under Black
in acetone of the unknown and a standard Powder, Analytical Procedures
proplnt contg C black is measured at wavelengths Detn of carbon in expls and proplnts as
such that the absorption by other constituents of practiced at PicArsn has been described in
proplnt is very small. The percentage of C in several CLR (Chemical Laboratory Reports) and
the unknown is calcd from that in the standard then later in GLR (General Laboratory Reports).
by the application of Beer’s law to the Most of these repts are not available, however,
absorption data accdg to Reese (Ref 16)
A similar method is now included as a The methods for detn of carbon in these
Military Standard (Ref 15), but accdg to Liszt repts involve the solution of all other
(Ref 17), it is applicable only when calibration is ingredients present in expls or proplnts by
done with carbon black identical with that used various solvents and weighing the residue as
in the manuf of the proplnt under test carbon. Carbon black is distinguished from
The gravimetric method using nitric acid graphite by. appearance, ease of ignition or by
has been also used in France, but Parpaillon et x-ray diffraction pattern (Ref 16)
al (Refs 11 & 12) prefer to use coned hydrogen R e/s: l)M.Berthelot, CR 114, 317- 18(1892)&
peroxide in alkaline soln instead of nitric acid. 129, 1002- 5( 1899); JCS 62 I, 753(1892) & 78 II,
They came to the conclusion to try using H202 172( 1900) (Analysis of org substances by
after reading in Ref 7 the description of method of combustion in compressed oxygen in calorimetric
Drs E, & W. Berl, who decompd the nitrocompds bomb) 2)W.Hempel, Ber 30, 202- 11(1897) &JCS
by means of 30% HZ02 in alk soln. Parpaillon 72 II, 189( 1897)( Elementary analysis under
et al slightly modified the method of Berl and pressure in a closed bomb) 3)M.Badoche, Bull-
applied it to detn of graphite or carbon black in F r [5] , 4, 232( 1937)( Combustion of nitrogenous
proplnts substances in calorimetric bomb) 4) E. Burlot, MP
procedure of Parpaillon for Detn of C in NC- NG 29, 226- 79(1939)(Study of calorimetry of expls)
propellant: a)place an accurately weighed 2g [Errata for this paper are given in MSCE 30,
sample of proplnt in an Erlen fl, add ca 4ml ale, 275- 9(1943)] 6)A.Boivin, MSCE 30, 9-13
15ml distd w and 25ml coned H202 (ca 30%) ( 1943)(Detn of C & H in compds contg N) 7)
b) Add 25g KOH in pellets, while gradually Clift & Fedoroff, vol 3, suppl NO 2 (1944),
cooli~g the flask with tap w and then heat the Errata & Additions, p 18 (to VOI 1, chap 2)
flask on a water- bath at 75° until the liq 8)P .Jovinet & S. Courtecuisse, MSCE 32, 16-20
becomes nearly clear C)COOI to RT, add 30ml ( 1945)(Modification of Duma’s method) 8a)
H202 and heat for 5mins at 75° d) Add another J .JDonovan, OSRD Rept 5842, NDRC, Div 3,
30ml H202 and heat for 5mins e)Cool and add a Seen H, Series P (1945) 9)S. Courtecuisse,
few mg of EtCentr (to facilitate the transfer of C MSCE 36, 147- 50( 195 l)(Modification of
from w to ether layer as in operation g) f)Boil Boivin’s method described in Ref 6) 10)
the mixt for 10mins, cool to RT, dilute with 100ml M. Thomas, MP 34, 401-11 (1952) (Rapid method
distd w and add coned HCI until the liq becomes of detn of C) 1 l)M.Parpaillon, MP 34, 419- 20
distinctly acidic g) Transfer the mixt ( 1952)(Detn of C black as a residue after
quantitatively to a 1000ml separator funnel destruction of other ingredients of double- base
provided with a stopper and add 100ml of ethe~ proplnts by treating with hydrogen peroxide in
Close the funnel and shake in order to transfer alkaline soln) 1 la) ’’ASTM Standards” (1955),
the carbon from w to ether layer h)If all C we,nt Part 4, D 561- 46,p 45(6pecs & tests for carbon
to the ether layer, discard the aq layer and run blk) 12)M.Parpaillon & S. Rigal, MP 37, 305-17
the ether layer thru a tared sintered glass ( 1955 XDetn of graphite in proplnts by methods
crucible of small porosity contg a disc of filter, similar to that described in Ref 11) 12a)
paper i)Dry the crucible and weigh S. Lader, PATR 2409( 1957)(Detn of carbon in
Note: If carbon does not separate from aq layer inert org expl intermediates) 13)USSpecifications:
or adheres strongly to the walls of the separator a)Acetylene Black, MIL- A-3850, superseding
funnel, add a small amt of a wetting agent (such PXS-1281 b) Charcoal for Use in Ammunition
as Na sulforicinoleate), shake the funnel and JAN- C- 178A(1) and c)Graphite for Use in
proceed as in opns h & i Ammunition JAN- G- 155(1) 14)Military
 c 59

Standard MIL- STD- 286A, Method 309.1.2, hydrocerussite), 2PbC03’Pb(OH)2; mw 775.67,

Carbon Black (Gravimetric Method) 15) wh amor powd, mp dec 400°, d 6.14; poisonous
Military Standard MIL- STD- 286, Method 309.2.2, compd (Ref 12,pp 816- 17). See also Spec
Carbon Black (Photometric Method) 16)E.Reese, MIL- L- 18618 (I)
PicArsn, private communication (1962) 17) Magnesium Carbonate(al so called Magnesite or Mag-
N. Liszt, PicArsn, private communication(1962) nesia Alba), ,MgCO$; mw 84.32, CO1 rhmbpowd, mp
dec 350°, d 3.04 (Ref 5,p 505). (See also Spec
Carbonaceous Material. Any material relating MIL- M- 11361A)
to or contg c such as woodmeal, sawdust, Manganese Carbonate(also called Dialozite or
cereal flours, lignite, coal, peat, bark, cork & etc. Rhodochrosite), MnCO,; mw 114,9, rose- colored
It is used as the fuel ingredient of composite expls rhmb trysts, mp dec on heating, d 3.13 (Ref S,p
5 12). (See also Spec MIL- M- 13667)
Carbonates and Bicarbonates. Carbonates are Potassium Carbonate(also called Potash or Sal
the salts of carbonic acid and contain the Tartar), K2 CO~; mw 138.2, CO1 monoclinic trysts,
C03= radical. Bicarbonates, also called acid mp 900° (dec), d 2.2 (Ref 5,p 677). It is used as
carbonates, are salts contg the monovalent a reagent, in photography, in medicine, and in the
radical HC03 - . All carbonates are readily prepn of K picrate, a primary expl (Ref 4,p 5).
decompd by acids; carbonates of the alkali metals (See also Spec O-P- 552C)
are SOI in w, giving an afkaline reaction; ail Sodium Carbonat~also called Soda, Washing
others are insol in w (Ref 5,pp 168-9 & Ref 7). Soda or Soda Ash), N~CO,; mw 106.00, wh
Carbonates are formed by the action of C02 trysts, mp 851°, bp dec on further heating, d 2.48
on a soln of alkali, but if excess of the gas is (Ref 5,p 780 & Ref 12,p 11 14). It is used as a
passed into the soln, a bicarbonate results. reagent, in the manuf of various them products &
Bicarbonates are SOI in water, and easily in other industries, and in various expl compns.
decompd by heat with the reformation of the normal (See also Spec O-S- 571E)
carbonate Strontium Carbonate(also called .%rontianite),
Some of the carbonates used in expls or SrC03; mw 147.6, CO1 rhmb trysts, mp dec 1155°,
pyrotechnics include the following: d 3.62 (Ref 5,p 811)
Ammonium Carbozate,(NH4)2 C03; mw 96.09, Zinc Carbonate, Etasi~also called Tutia),
CO1 cyt plates; S1 toxic (Ref 12,P 275). See ZnC03“H20; mw 143.40, wh rhmb trysts, mp dec
also Spec MIL - A- 13938. DeMent (Ref 14) used 300°, d 4.42 (Ref 5,P 922). See also Spec
this compd in smoke producing compns; and MIL-’ Z- 12061. The anhyd salt is listed in Sax,p
Stevenson (Ref 11) used it to vaporize 1267
diphenylchloroarsine & other smokes The principal bicarbonates used in expls
Barium Carbonate, BaCO~; mw 197.37, wh powd, include the following:
mp 1740 at 90atm, bp dec, d 4.43; this compd is Ammonium Bicarbonate, NH4HC03; mw 79.1, COI
poisonous when ingested (Ref 12,pp 331- 2). It rhmb or monoclinic trysts, mp dec 40-600, d 1.59
is used in expl mixts & in pyrotechnics. (See (Ref 5,p 47). It is used in some compns(Ref 6)
also Spec JAN-B- 624) Potassium Bicarbonate, KHC03; mw 100.1, CO1
Calcium Carbonate(also called Calcite or transparent monoclinic trysts, mp dec on heating,
Aragonire), CaCO~; mw 100.09, mp dec 825° and d 2.17 (Ref 5,p 676). It is used as a combustion
1339° at1025 atm, d 2.70- 2.95; Q: 2886cal/g controlling agent in some pyrotechnic smoke
(Ref 10); S1 toxic (Ref 12,p 425- 6). This compd compns (Ref 8), (See also Spec MIL-P-3173)
has been used in expl mixts, pyrotechnics, and as Sodium Bicarbonate(also called Acid Sodium
a stabilizer for NC (RefS 1 & 3)(See also Spec Carbonate or Baking Soda), NaHC03; mw 84.01,
JAN- C- 293) wh opaque powd or CO1 trysts, mp dec 270°, d
Lead Carbonate(also called Cerussite), PbCOa; 2.21 (Ref 5,P 779); Q~ 2680cal/g (Ref 10).
mw 267.22, wh powd, mp dec 315°, d 6.6; this See also Spec O-S- 576B. It was used in a type
compd is poisonous (Ref 12,pp 816- 17). It has of permissible expl, contg large amts of NaHC03
been used in proplnts and it is claimed by & small amts of NG, called Bikarbit (Ref 13).
Hennining (Ref 2) that fouling of gun bwrels is Mixts contg as much as 95% NaHC03 and as
lessened by addg 1- 5% of PbCO~ to proplht little as 5% NG were still easy to initiate by
compns ordinary blasting caps. DonIan (Ref 9) reported
Lead Carbonate, Basic(also called White Lead or that NaHC03, when added to cellulose material,
 C 60

acts as a flame retarding agent and as a by- product in the manuf of ethyl
Re{s: l)MarshaHl(1917), 186&2(1917),641 alcohol by yeast fermentation of carbohydrates
2)C.Henning, USp 1357865 (1920 )& CA 15,315 (Refs 1,3,6,8,9 & 13). It is shipped as cubical
(1921) 3)P.Demougin &M. Landon, MP 27, 182 blocks(dry ice) in special refrigerated cars &
-89(1937 )& CA 31,8200(1937) 4)Davis (1943) trucks and as a compressed liq in steel cylinders
5)Hackh’s( 1944) 6) Kast- Metz( 1944), 20 7) or tanks
Partington(1950), 623 8) L. Finkelstein& This compd is used extensively in many
S. J. Magram, USP 2543006(1951) 9) J. E. Dolan, industries: for example, in carbonating beverages,
Chem&Ind 1952, 368-71 &CA 46,7330(1952) as a refrigerant , in fire extinguishers, for the
10)P. Tavernier, MP 38, 312, 332(1956) 11) destruction of vermin, as a fertilizer, and in the
R.Stevenson, USP 2730482( 1956) &cA 50, explosives industry. According to Ferrell et al
15008(1956 12)Sax(1957) 13)pATR 2510 (Ref 2), blasting operations maybe conducted by
(1958 ),p Ger 11 14) J. DeMent, USP 2995526 gasifying a chge of Iiq C02 in a cIosed cartridge
(1961) by heat produced on vaporization of an elec
conductor. William s(Ref 4) used solid COZ as a
Carbonation. I)See Carbonization 2) Thepre- tamping chge with various blasting chges loaded
cipitation of lime by C02, as in sugar refineries into bore holes. The use of a device for blasting,
3)The saturation of water with C02, as in soda with a mixt of C02 & K120 both in the form of
water manuf; more properly known as snow, is described by Weber(Ref 5). The mixt is
car bonatation heated to cause its instant vaporization when
Re/: Hackh’s (1944), 169 desired. Podbel’skii & Ermuzevich(Ref 7) patented
a heating compn, constg of a mixt of naphthalene
Carbon Bisulfide. Same as Carbon Disulfide & KC103which was ignited electrically and used
CO detonate solid C02 expls (see also Cardox
Carbon Black. See under Carbon Blasting Cartridge). In the form of dry ice, carbon
dioxide is used extensively in them labs
Carbon Carbonite. An explcompn: Knitrate 34, Re/s: l) Mellor 6(1925), 1-.78 2) D. Ferrell et al,
NG 25, wheat flour 38.5, Ba nitrate 1, ground tan uSP 1610274(1926) & CA 21, 497(1927) 3)
1 & soda ash O.5% Pepin Lehalleur(1935), 360-62 4) V. H. Williams,
Re/.’ CondChemDict(1942), 288 (not found in USp 2031 O84(1936) & CA 30, 2388(1936) 5)
later editions) G. Weber, USp 2102245(1937) & CA 32, 1456(1938)
6) Thorpe 2(1938), 323-28 & 8(1947), 547 6a)
Carbon Dioxide or Carbonic Anhydride, C02; mw Davis(1943), 277, 323 & 326 7)G.N. Podbel’skii &
44.01; col,odorless gas or a wh snowlike solid D. V. Ermuzevich, RUSSP 65029(1945) & CA 40,
called “dry ice”, fr p --57° at 5.2 atm, bp -78° 7633( 1946 8)Kirk & Othmer 3(1949), 125-42;
( sublimes), d 1.56 at -79°(solid), d 1.10 at -37° 7(1951), 855 & 1st Supplement (1957), 36, 497,
(liq), d 1.53 at RT(gas); sol in w, sl sol in ale; 512, 515, 524, 892, 895 9)Partington (1950),
MAC 5000 ppm in air or 9000 mg/cu meter in air. 618-22 10)W .Pumpel, MittChemForsch- InstInd
Carbon dioxide in generally regarded as a simple Osterr 4, 113- 17(1950) & CA 45, 2603(1951) 11)
asphixant; signs & symptoms preceding asphixia F. A. Miller et aI, SurgForumProc 37th ClinCongr
are headache, dizziness, shortness of breath, AmCoUSurgeons 1951, 35- 40(1952) & CA 47,
muscular weakness, drowsiness & ringing in the 1296(1953) 12)Sax(1957), 436-37 13) Faith,
ears. Removal from exposure to C02 results Keyes & Clark (1957), 219-27
in rapid recovery. Contact of C02 snow(dry ice)
with the skin can cause a burn (Ref 12). See also Carbon Disulfide and Derivatives
Rumpel(Ref 10) and Miller et al(Ref 11) Carbon Disulfide or Carbon Bisulfide(calIed
Carbon dioxide issues in abundance from Schwefelkohlenstaff, Kohlendisulfid or
the earth, it occurs in mineral springs, it is Dithiokohlensaure anhydrid in Ger), CS2, mw 76. 13;
formed during respiration of mammals and passes CO1 liq nearly odorless when pure, fr p -111°, bp
into the atmosphere, and is evolved in the 46.5°, fl p -22°F(cc), d 1.261 at 20°, autoign
fermentation process & in the decay of org matter. temp 257° F, vap press 400mm at 28°, vap d 2.64;
It is produced commercially from the decompn of sol in alc or eth; nearly insol in w(Refs I & 16).
carbonates, by the combustion of carbonaceous The MAC is 20ppm in air or 62mg/cu meter of air.
materials such as coke, coal, oil & natural gas The chief toxic effect of CS.L is on the central

. . ..— .— —
!
 C61

nervous system; it acts as a narcotic & anesthetic 4165( 19so) 12)W.Rumpel, MittChemForsch
in acute poisoning with death following from -InstInd Osterr 4, 113-17(1950) & CA 45, 2603
respiratory failure. Its anesthetic action is much (1951) 13)Partington (1950), 635-37 14)
more powerful than that of chloroform. In chronic M. G, Zabetakis & G. W. Jones, IEC 45, 2079-80
poisoning, the effect of CS2 on the central (1953) ~ CA 47, 11737(1953) 15)E.Charles, USP
nervous system is one of central & peripheral 2670277(1954) & CA 48, 4784( 1954)( Apparatus
damage which may be permanent if the damage is for continous production of carbon disulfide) 16)
severe(Ref 16). See also Amor (Ref 11) & Rumpel Sax( 1957), 437-38 17) Faith, Keyes & Clark
(Ref 12) (1957), 228-32 18)CondChemDict (1961), 219
Carbon disulfide is produced by reacting
charcoal & sulfur in the presence of heat Carbon Disulfide Monoazide, N3 ,CS2H. This
furnished by electrothermal or retort methods. compd is described in Vol I,p A632. L as
Another process has been developed in which Azidoditbr’ocarborzic Acid, Lieber et al (Ref 2)
natural gas is used as the source of carbon. With assigned to it(based on IR spectra), the
a catalyst such as activated alumina, CS2 in thiatriazole structure, H —N , naming it
yields of 90% may be produced by reacting I moIe Y IJ
SC.S.N
methane(natural gas) with 2 moles sulfur at
approx 700 °(Ref 17)(See also Refs 7,10,13 & 15) 4H, 1,2,3,4- tbiatriazoline- 5- tbione
Liempt & deVriend(Ref 3) conducted Re/s: I)13eil 3, (86), [159] & {356} 2) E. Lieber
studies on the expln of CS2- NO, CS2 - N20 and of et al, JOC 22, 1750(1957)
CS2 - N20- NO mixts. The expl props of a mixt of
CS2 & N02, called “Myrite”, was investigated by Carbon Disulfide, Azido Derivative, A misnomer
Bain(Ref 5) but due to its relative sensitivity to for Bis - (azidothioformy i)-. disulfide(qv)
rifle bullet impact and its relatively low rate of
deton & brisance was not considered favorably as Carbonic Acid, HZC03. The soln of co in ~.I o
a military expl. The flammability of CS2 in mixts exhibits feeble acid props; it is unstable, 2 however, 2

of air & water vapor was studied by Zabetakis & and has never been isolated; it is known only in
J ones(Ref 14) who found that the min amt of O the form of its saIts (carbonates), acid salts
reqd for the mixt at 100° & Iatm press is 7.6% by (bicarbonates), amides (carbamic acid or urea),
vol. According to Roedler(Ref 9), the danger of and as acid chlorides (carbonyl chloride). This is
expln & fire is great in the use and storage of also an old term for carboxylic acid
CS2 (See also Refs 1,2 & 8) Ref: Hackh’s(1944), 169
Carbon disulfide is used in viscose rayon,
cellophane,for the manuf of carbon tetrach~oride, Carbonic Acid, Azidothio Derivatives. See VOI 1,
in veterinary medicine; as a SOIV in paints, p A632ff of this Encyclopedia
rubber, textiles, matches; and as a fumiganr,
preservative & pesticide(Refs 6 & 18). It is Carbonic Anhydride. See Carbon Dioxide
highly dangerous when exposed to heat, flame,
sparks or friction. Carbonides. See Carbides
Re/s: l)Beil 3, 197, (179), [139] & {320ff}
2)MelIor 6(1925), 94-118 3) J. A. M.vanLiempt & Carbonites. Permissible straight dynamites used
J .A.deVriend, Rec 52, 160-68, 862- 68(1933)& in Germany(Refs 2 & 4), GtBritain (Ref 2,p 402)
Rec 53, 760- 68(1934) 4)Thorpe 2(1938), 328-44 and at one time in the US(Ref 3,p 351). In France
5)C.J.Bain, PATR 1030(1940) 6)Davis(1943), they were used in modified formulations under the
48,119,225,227,354 & 438 7) A. Towers, names of ‘tGrisoutines’’(Ref 1 & Ref 2,p 402)
SchoolSciRev 29, 307- 1O(1948) & CA 43, 2826 The principal components of Carbonates are:
( 1949)(A short review on production & uses) 8) , NG(gelatinized or nor with collod cotton), K or Na
Kirk & Othmer 3(1949), 142-48 9)F.Roedler, nitrate and spent tan bark or woodmeal. Some
Desinfekt u ScMdlingsbeKdmpf 41, 211-14(1949) Carbonates contain Ba nitrate, K bichromate, Amm
& CA 46, 11564(1952) 10)ResInfoService Rept oxalate, gelatinized silicic acid and soda ash or
No 95810, Translation of Ger Pat Application No Mg carbonate
34369D(Feb 1949)( Process for producing carbon Typical Ger Carbonits are listed in Ref 2,p
disulfide by heating methane with H2S) 11) 401, Ref 3,p 353 & Ref 4,p 26. Typical Brit
A. J, Amor, Paint Manuf 20, 89- 93(1950) & CA 44, Carbonates are listed in Ref 2,p 402( See also
 C 62

Carbon Carbonite, Coal Carbonite, Gelatin reaction); as a by-product in them reaction; and
Carbonite,Kohlencarbonit, Haylite No 1, OakIite by combustion of org compds with a limited amt of
No 1 and Phoenix Powder O (Ref 21). A iab method for the prepn of pure CO
The Ammoncarbonit is described in Vol 1,p from formic acid & coned H$04 is described in
A293 of this Encyclopedia Ref 3(See also Refs 1,2,5,6,7,10 & 16)
Refs: l)H.Dautriche, Mp 15, 120- 22(1909-10) Carbon monoxide burns in air or O with a
2)Naotim, NG(1928), 401-2 3)Davis(1943), 351-3 bright bIue fIame, forming C02. A mixt of 2 vols
4)PATR 251 O(1958), 25-6 CO & 1 vol O expl when ignited by a spark, The
dry gases do not expl unless a trace of moisture,
Carbonization. l) The transformation of org matter or a gas which contains H and so produces H20 on
into charcoal 2)The distillation of coal, as in gas combustion in 0, is present. This expl reaction
& coke manuf(Ref 1). See also Refs 2 to 7, incl has been studied by a number of investigators(Refs
Re/s: l) Hackh’s (1944), 169 2) LV.Gebler, 4,11,12,14,15,17,18 & 19). The spontaneous
IzvestAkadNauk, OtdelTekhNauk 1948, 873-82 & ignition of CO and some of the factors controlling
CA 44, 4228( 1950) (Coking of the gas coals of the it are discussed by Warren(Ref 13)
Kusnetsk coal fields) 3)A.Thau, t ‘La Distillation Carbon monoxide is used in org synthesis,
~ Basse Temp~rature des Combustibles”, as a fuel, in metallurgy, and in Zn white
W. Knapp, Halle( 1949), 222pp; Reviewed in ‘JLJsines- pigments(Ref 21). More details of uses of CO
Gaz 74, 259(1950) 4)Y.Mayor, ‘<Combustible are given by Kirk & Othmer (Ref 5)
Solids”, SocProds Documentaires, Paris (1950), Re/.s: l)Mellor 5(1924), 904ff 2)Thorpe 2(1938),
232pp; Reviewed in JUsines Gaz 74, 259(1950) 344–51 2a)Davis(1943), 276-7, 323,327 & 352
5)H.Winter, “Taschenbuch fiir Gaswerke, 3)Inorg Synth 2( 1946), 81-5 4)S.H.Ash &
Kokereien, Schwelereien, und Teerdestillationen”, E .W.Felegy, US Bur Mines Bull No 47(1948), 202
6 ed, W. Knapp, Halle(1950), 659pp; Reviewed in pp & CA 44, 4679(1950) 5)Kirk & othmer 3
Gas*u Wasserfach 92, 67( 1951) @K. J, Nelson, (1949), 179-91 6)W.Reppe, Experiential 5, 93-11o
USP 2549117(1951) & CA 45, 5910( 1951) (Fluidized (1949) (Recent developments in the chemistry of
carbonization) 7)H. J .vonAlberti, ‘ ~Der acetylene & CC)) 7) Partington(1950), 627-31 8)
Braunkohlenschweler” (B6hlener Schwelfibel), A ,Grut, “Chronic Carbon Monoxide Poisoning”,
W .Knapp, Halle(195 1), 79PP; Reviewed in Munskgaard, Copenhagen (1950), 229pp;
BraunkohIe 4, 92(1952) Reviewed in RassMedInd 19, 295(1950) 9)
W. Rumpel, MittChemForsch-InstOsterr 4, 113-17
Carbonize. To convert to carbon; to char or burn ( 1950) & CA 45, 2603(1951) (Causes & prevention
incompletely of poisoning in them plants) 10)J .Schmidt,
Re/: Hackh’ s(1944), 169 “Das KohIenoxyd”, Geest & Portig, Leipzig( 195o),
366pp ll)G.B.Kistiakowsky et al, JChemPhys
Carbon Monoxide, CO; mw 28.01; CO1 & odorless 20, 994-1000(1952) & CA 47, 1931(1953) 12)
gas, fr p -199°, bp -190°, d(gas) 1.250 g/liter at R. E.Duff & H. T. Knight, JChemPhys 20, 1493-95
0°, d(liq) 0.793, vap d 0.967, autoign temP (1952) & CA 46, 11688(1952) 13)D.R.Warren,
1204°; S1 sol in w; readily absorbed by a soln of Fuel 33, 203-8(1954) & CA 48, 6126(1954) 14)
cuprous chloride in HCI or in NH3; its MAC is J .P.Toennies & H. G. Wagner, ZEIektrochem 59,
100 ppm in air or 115mg/cu meter of air. Carbon 7-15(1955) & CA 49, 8602( 1955) 15)H. G. Wagner,
monoxide has a great affinity for hemoglobin of ZElektrochem 59, 906-9(1955) & CA 50, 4508
the blood and by combining with it renders the ( 1956) 16)P.A,Paramonov, GornyiZh 1955, No
blood incapable of carrying oxygen to the tissues. 10, 49-55 & CA 50, 6049( 1956)( Mechanism of CO
Concns from 30 to 50% co cause severe headache, formation in mine air during blasting) 17)
mental confusion, impairment of vision & coilapse A.S.Gordon & R. H. Knipe, JPhChem 59, 1160-65
or fainting; 50 to 60% cause unconsciousness & (1955) & CA 50, 2174(1956) 18)W.Roth et al,
death if exposure is long; concns of 80% result in JPhChem 60, 512(1956) & CA 50, 12481(1956)
almost immediate death(Ref 20)( See also Refs 1, 19) F.0t4sek, Uhl[ (Czechoslovakia) 6, 90-3
2,5,8 & 9) (1956) & CA 50, 11018(1956) 20)Sax(1957),
Carbon monoxide is obtained almost pure by 438-39 21)CondChemDict (1961), 220
introducing a mixt of O & C02 in contact with
incandescent graphite, coke or anthracite; by Carbon Pernitride. See Cyanazide under Cyno
action of steam on hot coke or coal (watet gas Compounds and Derivatives

-.
1
 C63

Carbon Tetrabromide (caIled Tetrabrommethan, tubular pressure reactor at the duPont

Kohlenstofftetrabromid or Tetrabromkohlenstoffin Experimental Station, Wilmingt~n, Del(Ref 8). On
Ger), CBr4; mw 331.67; colmonocIcrysts, mp one occasion, expln took place at a temp of 94°
(alpha) 48.4° & (beta) 90.1°, bp 189.5°, d 3.42, and a press of 14500psi only 20mins after the
vap press 40mm at 96.3°; sol in alc or eth; insol reaction started. In the second example the
in w. Other props & methods of prepn are given reactor was charged with CC14, HZO & CZH4 and
in Refs heated with agitation atllOO and a press of 9600
Re/s: l)Beil 1, 68, (17), [35] & {92} la) Davis psi, a violent expht resulted. In both examples
(1943), 375 2)Hackh’s(1944), 168 3)D.E.Lake & dibenzoyl peroxide was the reaction initiator.
A. A, Asadorian, USP 2553518(1951) &CA 46, Precaution essential for avoiding these explns are
2561(1952) 4)Sax( 1957), 440 given by Joyce(Ref 8). The expln of acetyIene
mixed with oxygen or air under high press, and
Carbon Tetrachloride(called Tetrachlormethan, the effects of added substances are described by
Kohlenstofftetrachlorid or TetrachIorkohfens toff Kiyama et al (Ref 17); addn of CC14 or water
in Ger), CC14; mw 153.84, CO1 liq having a heavy elevates the. expln temp, however, when expln
ethereal odor, fr p -22.6°, bp 76.8°, d 1.597 at does take place it is more violent than without the
20°, vap press 100mm at 23°; sol in A=, eth additives. Lindeijer (Ref 11) reported that a mixt
chlf, benz or petr eth; v S1 SOI in W; MAC 25ppm of CC14 & powd Al resulted in a fatal expln
in air or 157mg/cu m of air(Refs 1 & 20). Carbon Carbon tetrachloride is used in refrigerants,
tetrachloride has a narcotic action resembling that in metal decreasing , as grain fumigants &
of chloroform, although not as strong. Exposure to insecticides, in fire extinguishers, as dry
high concns of CC14 may cause unconsciousness cleaning solvents, for chlorinating org compds and
& even death if exposure is not terminated; lower as a general solvent(Refs 6 & 21)
concn.s result in severe gastro-intestinal upset, Re/s: l)Beil 1, 64, (12), [22] & {64} 2)
serious kidney or hepatic damage(Ref 20)( See E.A.Barrier, IEC 2, I6-19(191O) & CA 4, 669
also Refs 3,10,13 & 16) (1910) 3)Kohn-Abresr, AnnChimAnalChimAppl
Carbon tetrachloride is prepd by the 15, 199-207(1933) & CA 27, 3193( 1933)(Props of
interaction of CS2 & CI in the presence of a CC14, toxicity, detection in air, decompn by heat &
catalyst(iron) or by the chlorination of methane its behavior on analysis are described) 4)Mellor
or higher hydrocarbons at 250-400° (Ref 21). See 13(1934), 6i5 5)Thorpe 2(1938), 353-56 5a)
also Re~S 1,4,5,9,15,18 & 19. The crude product Davis( 1943), 145,152,181,216,398,402-3 & 447 6)
is purified by treating with caustic soln to remove Hackh’s(1944), 168 7)R.O.Bolt, c & EN 25,
sulfur chloride, followed by rectification 1866(1947) &CA 41, 5724(1947) 8)R.M.Joyce, C &
It is, itself, a nonflammable Iiq. Flash, EN 25, 1866-67(1947) & CA 41, 5724(1947) 9)
fire & expln tests on mixts of CC14 & naptha, as Kirk & Othmer 3(1949), 191-200 10)
detd by Barrier(Ref 2), showed that they are W. F. VonOettinger et al, ArchIntern Pharmacodyn-
combustion and expln-proof if such mixts contain a amie 81, 17-34(1950) & CA 44, 7426(1950) 11)
min amt of CC14. This amt varies, with the sp gr E. W. Lindeijer, ChemWeekbIad 46, 571(1950) & CA
of petr naptha, from 30 to 70%. The quenching 46, 7769( 1952) 12)C. W. Van Hoogstraten &
power of C02, CC14, CH3 Br & CH2ClBr for fires J. F. Van Elteren, ChemWeekblad 47, 866-75(1951)
of org combustible liquids and of wood shavings & CA 46, 2805(1952) 13) R. W. Van Hoesen
was detd by Hoogstraterr & Van Elteren(Ref 12) Korndorffer, P1astica(Delft) 4, 11-13(1951) & CA
who found that quenching power increased in the 49, 11178-79(1955) 14)E.H.Coleman, “A
foregoing order of agents, although the type of Comparison of the Extinguishing Effects of
fuel was also of importance Chlorobromomethane, Methyl Iodide and Carbon
Expl reactions have been reported in two Tetrachloride”, Fire Protection Assoc, London
labs working with ethyIene & CC14(Refs 7 & 8). (:952), 12PP 15)N,Trappeniers, “Le Princ~pe des
In the lab of the California Res Corp, Richmond, Etats Correspondants et les Diagrammes d’ Etat
Calif an expln occurred quite suddenly at 67° & du Tdtrachloture et du T#trabromure de Carbon”,
>2500 psi afier heating ca 2hrs a mixt of CC14, Palais Acad, BrusseLs(1952), 93PP 16)
C2H4 & a catalytic amt of benzoyl peroxide in a C. C. Comstock & F. W. Oberst, Arch Ind Hyg
std lab autoclave(Ref 7). Two other exampIes of Occupational Med 7, 157-67(1953) & CA 47,
uncontrolled reactions between ethylene & CC14, 12618-19(1953) li’)R.Kiyama et al, RevPhysChem-
which resulted in violent explns, occurred in a Japan 24, 41-48(1954) &CA 49, 12006(1955) 18)
 C 64

L. F.Hatch, Petroleum Refiner 33, No 12, 136-40 Carbonylazido-guanidine( called Guanidincarbon-

( 1954)(A review of production rates, processes s~ureazid in Ger), H2N.C(:NH).NH. C0.N3; mw
and end uses of chlorinated Cl’s & C2’S) 19) 128.10, N 65.61%; was obtd in the form of its
Faith, Keyes & Clark( 1957), 233-37 20)Sax Hydrochloride, C2H4N60+HC1; fine trysts, mp
(1957), 440-41 21)CondChemDict( 1961), 22o 157°, expl in a flame; very sol in w; insol in org
SOIVS; was prepd by treating a coned aq soln of
Carbon Tetrafluoride( called Tetrafluormethan, aminodicyandiamidine dihydrochloride with a
Kohlenstofftetrafluorid or Tetrafluorkohlenstoff in chlf soln of anhyd N205
Ger), CFO; mw 88.01; COI gas, fr p -184°, d 1.96 Re/s: l)Beil 3, 130 2) J. Thiele & E. Uhlfelder,
at -184°; formed as a by-product in the manuf of Ann 303, 112(1898)
Al from cryolite (Ref 2); can be prepd by the
action of F on SiC(Ref 3). Other props & methods (5’-Carbonylazido-pyridine)-l’,2’:4,5-tetrazole.
of prepn are given in Refs See under (5’-Carboxypyrido} I’ ,2’: 4,5-tetrazole
Re/s: l)Beil 1, 59, (8), [11] & {35} 2)
Hackh’s( 1944), 168 3)H.F .Priest, InorgSynth 3 Carbonyls. A group of compds of CO & metals,
(1950), 171 4)R.M.Mantell et al, USP 2684987 having the general formula MX(CO)Y. They are
(1954) & CA 49, 10354(1955) 5)M.W.Farlow, USP usually prepd by interaction of CO with heated
2709182( 1955) & CA 50, 6506(1956) 6) metals. Most carbonyls are highly toxic and
E. L. Muetterties, USP 2709184(1955) & CA 50, dangerous when heated. Some compds are reported
6498(1956) 7)M.W.Farlow & E. L.Muetterties, USP to be expl or very unstable:
2709 191( 1955) & CA 50, 6507(1956) 8)Ibid, USP ~ron Norzucarbonyl, Fez (CO)~; mw 363.8, orn hex
2732410 & 11(1956); CA 50, 15574(1956) 9)Sax trysts, mp dec 100°, d 2.09 at 18° (Ref 2,p 450 &
(1957), 441-42 Ref 6,p 79o)
Iron Perztacarbony~, Fe(CO) ; mw 195.9, yel to
Carbon Tetraiodide(called Tetraiodmethan, dk red liq, fr p -21°, bp 1058, fl p 5°F, d 1.453 at
Kohlenstofftetraiodid or Tetraiodkohlenstoff in 25°, vap press 40mm at 30.3° (Ref 2,p 450 &
Ger), C14; mw 519.69; octahedral red trysts, mp Ref 6,p 790)
l?1° (dec), d 4.32 at 20°; SO1 in alc or eth; insol Iron Tetracarborzyl, Fe(CO)a; mw 167.88, dk-grn
in w(Refs 2 & 5); other props & methods of prepn lustrous trysts, mp dec 140-50°, d 1.996 at 18°
are give’n in Refs 1 & 4. It has been investigated, (Ref 2,p 450 & Ref 6,p 791)
in addn to other tetriodo or related compds, for its Nickel Carbonyl, Ni(CO)4; mw 170.69, CO1
possible fungistatic activity(Ref 3) volatile liq or ndls, fr p -25°, bp 43, d 1.319 at
Re/s: l)Beil 1,74, (19), [39] & {104} 2) 17°, vap press 400mm at 25. 8°; MAC lppm in air
Hackh’ 5(1944), 168 3)1. Muirhead, AnnApplied or 7mg/m3 in air; expl range 2Z at 20 °(Ref 2,p
Biol 36, 250-56(1949) & CA 44, 10233-35( 195fJ) 570 & Ref 6,p 933-34). Badin et al (Ref 3)
4)R.E.McArthur & J .H.Simmons, InorgSynth 3 reported that vapors of this compd expl in air or
(1950), 37 5)Sax(1957), 442 oxygen at 20° and partial pressures as low as
15mm. The expln is preceded by a long&
Carbonyl Azide. See Carbonyl Diazide, Vol 1,p variable induction period
A528-L Potassium Carbonyl (called Hexaoxybenzolkalium
in Ger), K6(CO)G; mw 402.64, gray-red solid, mp
o-Carbonylazido-diphenylurea{calIed 2- [O expl on prolonged contact with air or in contact
-Phenyl-ureido] -benzoesiiwe-azid or N-Phenyl with w; was prepd by passing CO over heated K,
-N’- [ 2-azidoformyl-phenyl ] -harnstoff in Ger }, and also obtd a by-product in the prepn of K from
C6H~.NH.C0.NH.CGH4 .C0.N3; mw 281.27, N K2C03 (Ref 1; Ref 2,p 677; Refs 4 & 5; and
24.90%; trysts (from MeOH), mp 133°, detonates Ref 6,p 1038)
violently when heated in a flame; was prepd by Sodium Carborzyl, NaCO; mw 51, highly toxic (no
heating aniline with 2-azidoformylpheny lisocyante other props are given in Sax, p 1114)
(itself a violent expl when heated rapidly; See Re/s: l)Beil 6, 1199 2)Hackh’s( 1944) 3)
VO1 1,p A638-R) in benz E. J. Baldin et al, JACS 70, 2055-56(1948) & CA
Refs: l)Beil 14, [224] 2)H.Lindemann & 42, 7045(1948) 4)Kirk & Othmer 3(1949), 201 5)
W.Schultheis, Ann 464, 251(1928) & CA 22, Karrer(1950), 430 6)Sax( 1957)
3664(1928)
Carbonylurea, 0C(NH.C0.NH2); crpts, mp 231-5

1
 C 65

(Ref 1). Aaronson(Ref 2) prepd it by heating in an R e/s: l)Beil 9, 873 2)0. Widman, Ber 22,
autoclave mixt of examine (C0.NH2)Z & phosgene 2273(1889)
C0.C12. Attempts to nitrate it to obtain mono- or
dinitro- derivs were unsuccessful Dinitrocarboxyby drocinnamic Acid,
Refs: l)Beil 3, 72, (35), & [60] 2)H.Aaronson, HOOC.C6H2(N02)2 .CH2 .CH2 .COOH; not found in
PATR 1037(1940) Beil or in CA thru 1956

Carborundum. A trade name for Silicon Carbide,

SiC, a hard substance(Moh’s hardness 9.17),
which can be obtained by heating sand and coke
,with some sawdust in an electric furnace at high 3,4,6(or 3,5,6 )-Trinitr-2-carboxyhydrocinnamic
temp. The name c‘Carborundum” is also applied Acid, HOOC.C6H(N02 )3 .CH2 .CH2.COOH; mw
to other hard marerials, such as fused alumina. 329.18, N 12.77%; trysts, mp expl violently on
These materials are used as abrasives for heating; was obtd with ocher products on
cutting, grinding or polishing(Refs 2,3,5,6 & 7). nitration of 5,6,8-trinitrotetralin with KMn04 in
To a limited extent, Carborundum was used as a acct. Its Potassium salt, KC, oH6N30t o, yel
component of primers to increase their sensitiviness trysts, expl violently when heated in a flame
to friction & impact(Ref 4). Bain(Ref 1) found (Refs 1 & 2)
that incorporation of 5% of Carborundum in Refs: l)Beil 9, [622] 2)1. G. Schroeder, Ann
Tetracene produced a mixt sufficiently sensitive 426, 47(1922) & CA 16, 1764(1922)
for use as a cover chge for LA in primers
Re/s: l) C. J. Bain, PATR 859(1937) 2)Thorpe 2 Carboxymethylcelluose(CMC). A cellulose
(1938), 358-61 3)Hackh’s( 1944), 169 4)A11 & glycolate compd that has achieved great coml
EnExpls(1946), 34 5)Kirk & Othmer 2(1948), importance in recent years. The Sodium salt is
854-6fi49refs) 6)Sax(1957), 1100(Props & its most important deriv: CO1, odorless,
toxicity) 7)CondChemDict( 1961), 221 tasteless, non-toxic, hygro powd; combustible
when finely ground. The trademark for one tech
Carboxydiphenyl. Same as Biphenylcarboxylic grade coml product is “Carbose” (Ref 2).
Acid Sodium CMC is supplied in several grades,
depending upon viscosity & purity. Its prepn is
Carboxyhydrocinnamic described in Ref 1. It is used as a thickener,
Acid and Derivatives binder, stabilizer for emulsions, ingredient of
Carboxybydrocinnamic Acid or Carboxyphenyl detergents & in film-forming. The potassium
-propiorzic Acid [called /3-(Carboxy-phenyl) salt resembles the Na salt in many of its props.
-propionsaure or Hydrozimtsaure-( 2,3 or 4) Thel Ammonium salt is umstable and certain
-carbon s~ure in Ger] , metallic salts are insol in water
HOOC.C6H4:CH2.CH2 .COOH; mw 194.18. Three Refs: l) Groggins( 1958), 846-7 2)CondChemDict
isomers are described in the literature: (1961), 221, 1037
~-(2-Carboxyphenyl) deriv, ndls (from w), mp
165-7° (Ref 1); @-(3 -Carboxyphenyl) deriv, Carboxyoxanilic Acid.Same as Carboxyphenyl-
piths, mp 177° (Ref 3); and the oxamic Acid
P-(4-Carboxyphenyl) deriv, ndls (from ale), mp
277° & 294°, dec ca 280° (Ref 2). Other props & [I(or N’)-Carboxypheny l-lII(or N)-cyanoguanyl]
methods of prepn are given in Beil -triazene or [I(or N’)-Carboxypheny I-III(or N)
Refs.’ l)Beil 9, 872, (382) & [622] 2)BeiI 9, -cyanoamindino]-triazene {called l(oder 3)
873 & [622] 3)Beil 9, [622] - [2-Carboxy-phenyl] -3(oder 1)-cyanguanyl
-triazen-( 1); 2- [Cyanoguanyl-triazenol
Mononitrocarboxy bydrocinrzanzic Acid, -benzoes~ure; or [2-Carboxy-benzoldiazo]
HOOC.C6H3(N02).CH2 .CH2 .COOH; mw 239.18, dicyandiamid in Ger}, HOOC.CGH4 .N:N.NH.C”
N 5.86%. The ~-( 2-Nitro-4-carboxyphenyl) deriv (:NH).NH.CN; mw 232.20, N 36.20%; yel trysts
is described in Beil; trysts, mp 191-2°; readily (from MeOH), mp dec ca 98°; readily SO1 in hot
sol in MeOH; sol in hot w, alc or dil AcOH; ale; S1 sol in benz, eth or chlf; insol in w; was
insol in benz; was prepd by nitration of the prepd by treating diazotized anthranilic acid
parent compd using mixed acid (Refs 1 & 2) with dicyandiamid in alksoln. Its Silver salt
 C66

Ag2C9H6N~02+ AgC9H7N602, yel, geily like zinopyridine with K nitrite. This compd, on
ppt, expl on heating (Refs 1 & 2) oxidation with alk permanganate soln, yields
l?e~s: l)Beil 16, (410) 2)R. vonWalther & unstable tetrazoles.
W.Grieshammer, JPraktChem 92, 235(1915) & It forms salts and some derivs which are
JCS 110 1,172(1916) expl: Silver salt, AgC6H3N402, trysts, deflgr on
heating (Refs 1,2 & 3) and
Carboxyphenyloxamic (5’ Carbonylazido-pyridine)- 1‘, 2’:4, 5-tetrazole,
Acid and Derivatives N3.0C.C5H3N4; mw 189.14, N 51.84%; trysts
Carboxyphenyloxarnic Acid or Carboxyoxanilic (from’ ale), mp 103-4°, expl on heating in a flame;
Acid [called (Carboxy-phenyl~ oxamids3ure or S1 sol in cold alc or hot w; was prepd by treating
Oxanilsaure-carbons 6ure in Ger] , an aq soln of the hydrochloride of 5-carboxy-
HOOC.C0.NH.C6H4 .COOH; mw 209.15, N 6.70%. hydrazide-2-hydrazinopyridine with NsN02 (Refs
Two isomers are described in the literature: l&2)
2-Carboxy deriv (also called Kynuric Acid), ndls R e/s: l)Beil 26, 564 2)W.Markwald &
+ H20 (from w), becomes anhyd in vac at 60-70°, K.Rudzik, Ber 36, 1111, 1115-16(1903) 3)
mp (of hydrate) 199-200° (dec) and (of anhyd acid) V.vonRichter & R. Anschiitz, “The Chemistry of
200-10°; forms numerous salts (Ref 1) and the the Carbon Compounds” , vol 4, The Heterocyclic
3-Carboxy deriv, lfts + H20 (from w), at ca 210° Compounds and organic Free Radicals, Elsevier,
converts to oxanilide -3,3-dicarboxylic acid (Ref NY( 1947), 214 4) F. R. Benson, ChemRevs 41,
2). Other props & methods of prepn are given in 19(1947)
the refs
Re/s: l)Beil 14, 342, (541) & [222] 2)Beil 14, (3’-Carboxypyrido)-5’,6’:4,5-vic(or 1,2,3) -triazole
398 {called [Pyridino-2’.3’ :4.5-ttiazol] -carbonsaure
-(5’); or 5.6-Azimino-nicotinsaure in Ger},
5-Azido-3-carboxyphenyloxamic Acid,
HOOC.C0.NH.C6H3 (N3).COOH; mw 250.17, N
22.40%; yel substance (from w), readily SO1 in HOOC.C ‘= CH — C — -N
(3’) (4’) (5’)(4) (3)
hot w; was obtd bY pouring 5-amino-3-carboxy-
phenyloxamic acid into excess HC1, 34.14%; trysts + H20 (from w), mp becomes
diazotizing with NaN02, converting into the anhyd at 150°, dec ca 270°; sol in hot alc or
perbromide, treating with NH~ and adding HC1 to hot w; S1 sol in cold alc or cold w; was prepd by
ppt the product. This compd, when boiled with treating a HCI soln of 5,6-diaminopyridine-
dil KOH, is decompd into oxalic acid & carboxylic acid with NsN02
5-azido-3-aminobenzoic acid, It forms salts, some of which are expl:
[H2N.C6H3(N3).COOHI, S1 reddish ndls (from W) Amrnorzium salt, NH4,CeH3N402, trysts, defr on
which detonate when heated(Ref 1 & 2) heating; Barium salt, BaC6H3N402, trysts, expl
Re/s: l)Beil 14, 418 2)P.Griess, Ber 21, 1562 on heating; Copper salt, blue amor solid, expl on
( 1888) & JCS 54111, 826-7(1888) heating; Lead salt, wh trysts, exP1 on heating;
Note: No nitrated derivs were found in Beil and Silver Salt, AgzC6H2N402, amor solid,
expl on heating(Refs 1 & 2)
(5’-Carboxypyrido)-1‘,2’:4,5-tetrozole; 6-Carboxy- Re/s: l)Beil 26, 564 2) W. Markwald, Ber 27,
pyridotetrazole (Benson); or Tetrazolo [a] 1337-39 ( 1894)
-pyridinecarboxy lic Acid (Richter-Anschtitz)
[called 1.2. 3-Triaza-indolizin-carbons3ure-(6) in Carboxytriazole and Derivatives
Ger] , 3-Carboxy-a-sym(or l,2,4)-triazole [ called
1. 2.4-Triazol-carbons ~ure-(3 bezw 5) in Ger] ,
(4’) (39) :2’)(5) (1). (2)
H~~~-~+-~ HC–NH—N HC:N —NH
; mw 164.12, N 34.14~o; II
N —C
II. C~H Ilor C.COOH
HOOC.C =CH—N—N Nz
(5”1 (6’) (1’)(41 (3)
HC:N.N
CO1 ndls (from w), expl on heating above 338°; I II ; mw 113.08, N 37.16%; trysts,
sol in hot w; was prepd by treating an aq soln of HN —C.COOH
the hydrochloride of 5-carboxy-2-hydra- mp 137° (dec), begins to decomp at 80~ almost
 C 67

insol in alc or w; was prepd from 3-methyl-asyrn Ester, ON.N:C.NH.N

-triazole by oxidn with KMn04 soln. It decomp,
on heating or by boiling water, into asym
I
HN—
II
C. CO0.C2H~
-triazole (Refs 1,2 & 3). It forms a Copper salt, and other desmotropic forms; mw 185.15, N 37.83%
CU(C3H2N302)2, yel-grn tryst powd which is solid substance, mp explodes on heating or by
mildly expl / friction; was prepd by treating the ethyl ester of
12e/s.’ l)Beil 26, 28~1 2)A.Andreocci, Ber 25, 5-amino.3-carboxy-a-sym-triazole with aq NaNOz
225-30(1892) 3)J.A.Bladin, Ber 25, 744(1892) + HC1, under cooling (Refs I & 2). The ester is
a more powerful expl than its acid
4-Carboxy-a-vic(or 1,2,3)-triazole [ called 1.2.3 Re/s; 1 )Beil 26, 311 2) W. Manchot & R.NoII, Ann
-Triazol-carbonsaure-(4 bezw 5) in Ger] , 343, 8-9( 1905)
I-IC.NH.N
II II or Carburant(Fr). Combustible fuel for engines or
HOOC.C—”N rocket motors
HC:N.NH HC.N:NH
! or Ill: Cardox. It is a blasting device first introduced ca
HOOC.C=N HOOC. C––NH 1920 in the coal mines of US and approved in
mw 113.08, N 37.16%; Ifts (from coned HCI) 1928 by the But Mines for use in gaseous and
or tryst solid (from w), mp 211-20° (dec, dusty coal mines. Essentially, Cardox is a
depending upon conditions of heating); heavy-walled steel cylinder (cartridge) contg at
readily sol in hot w; S1 sol in cold w or ale; its lower end a hole which is covered hermetically
almost insol in eth, chlf or AcOH; was first with a thick steel diaphram(release disc). Its
prepd from 2-aminophenyl-vic-triazole carboxylic upper, open end is covered with a detachable
acid with KMr@4 in aq NaOH (Refs 1 & 2). Other head contg an electric firing device(igniter) and a
methods of prepn are given in Refs 1,3,4 & 5. on heating element consisting of a mixt of an
heating above the mp, it yeilds vic-triazole. Its oxidizer and fuels. For example the Brit Cardox
Silver salt explodes on heating (Ref 2) described in Ref 5, contains: K perchlorate s5,
Re/s: l)Beil 26, 277 2)0. Baltzer & H.vonPechmann, kerosene 8.5, o-MNT 4.5, castor oil 0.5 & asbestos
Am 262, 317-20(1891) 3) T. Zincke, Ann 311, fibers I. 5%. After filling the cartridge with liq (or
317( 1900) 4)0. Dimroth, Ber 25, 1044(1902) 5) solid) carbon dioxide, the ensemble is placed in
A .Peratoner & E. Azzarello, AttiAccadLinceiRend the borehole(drilled into coal) and tamped. On
[51 1611, 320(1907) & JCS 92I, 980(1907) passing an elec current thru the igniter, the
combustibles of heating eIement are ignited and
5-Nitrosamino-3-carboxy-a-sym-trioazole [called the heat generated is sufficient to convert C02 to
5-Nitrosimino-l .2.4-triazolin-carbons~ue-(3); 5 a gas at a pressure of the order of 30000psi.
-Nitrosamino-l. 2.4-triazol-carbons~ure-(3); or 5 This causes rupture of the steeI diaphragm, thus
-Diazo-l.2.4-triazol-carbons~ute_(3) in Ger] , permitting the gas to escape with great force and
ON. N: C.NH.N rupture the seams surrounding the borehole
1 II
HN —C,COOH
and other desmotropic Cardox is flameless,
evolves no toxic gases.
non-brisant and
It breaks coal into fairly
forms. This compd is described in Vol I of this large pieces(Refs 1-6)
Encyclopedia as 5-Nitrosamino-a-sy m-triaole Addd Refs list various modifications of
-3-carboxyIic Acid under Aminotriazolecarboxy lic blasting cartridges using liq or solid carbon
Acids and Derivatives, p A270-R dioxide; and in Vol l,p Al 17 is briefly described
It was patented in France as a constituent the device called “Airdox” which uses
of priming mixts: 5-Nitrosamino-3 -carboxy-a-sym compressed air in Iieu of C02 (See also Ref 5,pp
-triazole 1-10, LSt 30-60%, and the remainder 137-42)
Sb2S3, Pb02, Ba(N03)2 & CaSi(Ref 2) Another flameless blasting cartridge is
R e/s: l)See Vol I,p A270-R 2)Deurxche Waffen- known as “Hydrox” (Ref 5,pp 127-33)
u ,Munitionsfrabriken AG, FrP 824130(1938) & Re/s: l)J .E.Tiffany, USBurMines RI 2920(1929)
CA 32, 5630(1938) (Description of “Cardox” cartridges) 2)pepin
Lehalleur(1935), 361 4)Thorpe 4(1940), 562 3)
5-Nitrosamino-3-corboxy-a-sym-triozole Ethyl Kirk & Othmer 3(1949), 149 4)Ullmann 9(1957),
 C 68

775 5)Taylor &Gay(1958), 123-7 6)Cook(1958),16 USP 2253115(1941) & CA 35, 8300( 1941)( Mecha-
Addrd Refs: a)D,Hodge, BritP 320226(1928) & nical blasting cartridge operated by gas pressure)
CA 24, 2606(1930); BritP 324617 (1928) &CA 24, p)G.N.Podbel’skii, Ugol’ 23, NO 3, 12-13(1948) &
3904(1930); Britp’s 328716& 328717(1929); CA CA 47, 7769( 1952 )( Cardox cartridge contg in its
24, 5499( 1930) ;BritP329636(1929) &CA 24, heating elements a mixt of K chlorate and
6020( 1930) ;BritP 332196( 1929) &CA 25,208 naphthalene)(Compare with Addnl Ref j)
( 1931 )( Blasting cartridges for use with compressed
carbon dioxide) b)D.Hedge, BritP 348657(1929) & Cargo hueca(span). Shaped Charge
CA 26, 849( 1932 )( Blasting cartridge contg C0.2
and heating element consisting of an elec igruter Carica a punta vuota(Ital). Shaped Charge
and mixt of K chlorate 68, Al 27 & paraffin 5%)
c) G. S. Rice, USP 1751659( 1930) & CA 24, 2606 CarilIon(Explosive), patented in France in 1894,
( 1930)( Blasting cartridge contg C02) d)D.Hedge, consisted of a hermetically closed vessel filled
& W. Eschbach, BritP 345284(1929) & CA 27, with mixt of hydrogen and oxygen produced on
1177( 1933) (Blasting cartridge contg C02, elec electrolytic decompn of water. The gas could be
igniter, primary chge of Pb(CNS)2 & KC104 and exploded by an elec igniter
a secondary chge of Fe & KMn04) e) A. C. Scott & Re/: Daniel(1902), 115
D.Hedge, BritP’s 354305, 354306 & 354342(1930)
& CA 27, 2303( 1933)( Blasting cartridges for use Carlisle Lumber Co, Onalaska, Washington,
with C02 contg in their heating elements O developed before WWII an explosive contg AN 85%
-carrying salts, such as K chlorate or perchlorate activated carbon (from Douglas fir) 10 & flaked Al
and combustibles, such as phenolformaldehyde 5%, which was suggested as being of possible
resin, nitrobenzene kerosene, castor oil, etc) f) interest as a military expl. Its props were detd
A. Ignatieff, MiningMag 48, 73(1933) & CA 27, at picArsn and found as follows: Explosion
2580( 1933)( Description of principles and applica- Temperature 28 l“(vs 290° for 80/20 Amatol);
tions of Cardox cartridges) g)L ‘air Liquide, FrP Friction Pendualum Test -negative; Gap Test 2“;
752086( 1933) & CA 28, 900( 1934) (Liquefied or Hygroscopicity -higher than Amatol; fmpact
solified gases used as blasting chges in mines Sensitivity, 2kg wt, BurMinesApp 87cm (VS 89 for
are rapidly evapd by a heating compn composed of Amatol); Minimum Detonating Cbarge(MF +
inorg~ic oxidizers, such as K chlorate, and Tetryl) >0.5g (VS O.10g for Amatol); Sand Test
combustibles, such as paraffin) h)A.C.Scott, 32g (VS 2i’.4g for Amatol or 38. 2g for TNT); and
BritP 397203(1933) & CA 28, 900(1934); USP Thermal Stability -less satisfactory than for
1957733( 1934) & CA 28, 4235( 1934)( Blasting Amatol
cartridge for use with compressed C02 or other It was concluded that this material has no
inert gas contains a heating element comprising advantage over 80/20 -Amatol or other AN expls
an O-carrying substance such as K perchlorate used for military purposes, such as for filling
thru which a resinous material such as “Elo” shells, bombs, land mines or as demolition
resin is distributed) i)D.Hedge & A. Ignatieff, c barges
BritP 405645(1934) & CA 28, 4602( 1934) (Cartridge Re/: A. J. Phillips, PATR 1038( I94O)
contg condensed gas, such as C02 and a heating
element comprising a Iiq mixt of an oxidizer and a Carlit or Karitto. A Japanese explosive, first
fuel) j)A.G.Suvorov, ZhpriklKhim 8, 341-5(1935) used during WWII as a bursting chge for mines
& CA 29, 677o( 1935 )( Cardox cartridge contg a and depth chges, and in demolition chges
heating element composed of K chlorate 90 & primarily to conserve”expls made from the
napththalene 10%) k)A.Ignatieff, BritP 32, 6463 limited supply of benzene and toluene. Its
(1938) & CA 32, 6463( 1938)( Blasting cartridges original compn was: Amm perchlorate 66, Si
contg compressed C02) l) L. D. Myers, USP carbide 16, woodpulp 12 & petroleum 6%; grey pdr,
2145366(1939) & CA 33, 3590-l(1939XBlasting nonhygroscopic, stable and safe to handle. It was
cartridges suitable for use with C02) m) believed that Si carbide aided in uniform
C. LSandoe, USP 2207205(1940) & CA 34, 8286 propagation of the detonating wave thru the
( 1940)( Blasting cartridge suitable for use with loosely packed pdr(Refs 1-3)
C02 or with compressed air) n) A. Ignatieff, Britp At present Carlit is used in Japan for
5 17417( 1940) & CA 35, 7195( 1941)(A CArdox industrial purposes and in some experimental
blasting carrridge) o) D. Ferrell & A. W. Helmholtz, solid rocket proplnts. Several modifications of
 C 69

industrial Carlits, have been produced since A powerful oxidizing substance first obtained in
WWII(Ref 3)( Compare with Type 98 Explosive, 1898 by Caro on grinding K persulfate (K2S20e)
also known as Haensosan-bakuy aku) with coned H2S04, allowing to stand for an hour
Re/s: I) Anon, “Handbook of Japanese and then pouring on ice(Ref 1). Edwards (Ref 2)
Explosive Ordnance”, OPNAV 30-3M( 1945), 29 reported prepn by reacting chlorosulfonic acid
2)Anon, ‘tMilitary Explosives”, TM 9=1910 (H0,S02 .Cl) with 90% H202 at low temp. One
(1955), 212 3)R.P.Antonelli, OTIA, sample stored overnight at 0° exploded when it
“Encyclopedia of Explosives”, OrdnLiaison was left for 10mins at RT. The cause has not
Group-Durham, NC( 1960), 28-9 been detd. In Ref 3 was reported a vioIent lab
expln when some acetone was inadvertently added
Carlsonites. Amm perchlorate expls patented, to a fIask contg some of Care’s acid
beginning 1898, by O. F. Carlson of Sweden R e~s: I)J .R.Partington, “A Textbook of
Inorganic Chemistry”, Macmillan, NY( 1950), 487
~%rnponents Designations 2)J.O.Edwards, C & EN 33, 3336(1955) & CA
. ..—— —— --- --------
1234 49, 14325(1955) 3) Anon, C & EN 38, 59(Nov 21,
NH4C104 1960)
40-80 51-80 60-70 89
Paraffin 10-25 10-20 - Carpet Bombing. See Bomb Carpet
Naphthalene 5-8 20 - -
Car.Prill, A blasting expl consisting of prilled
Charcoal 5-20 - 11
AN ca 91.6%, ground walnut shells ca 4.6% &
Petroleum - 10-20 - Diesel oil ca 3.8%. It belongs to the class of
Woodmeal 5-20 -- blasting agents called ‘ ‘Nitro-Carbo-Ni trates”.
It has been used in conjunction with dynamite (by
‘KOstalka’ ‘(residue 3-10 10-20 -
loading each borehole with both materiaIs) for
from distn of petro-
blasting operations in strip-mining, open
leum)
quarrying, construction of logging roads, etc
A devastating expln took place in the
downtown section of Roseburg, Oregon at 1AM
Accdg to Marshall (Ref 2), CarIsonites were
on Aug 7, 1959, when 4.5tons of t ‘Car-Prill” and
the first Amm perchlorate expls submitted to HM
2tons of dynamite were initiated by the intense
Inspectors of Explosives. Some of the mixts were
heat from a nearby warehouse fire. This expl
reported favorably, but no license was ever
caused property damage of ca 9million, killed 9
issued in the United Kingdom for these expls
and injured more than 125 persons
Re/s.’ l)Daniel(1902), 116 2)MarshaH,
Re/: Anon, “The Roseburg, Oregon, Fire,
Dictionary(1920), 20 3)Giua, Trattato 6(1959),401
Explosion and Conflagration”, Report by the
National Board of Fire Underwriters, New York
Carnauba Wax. See under Waxes
38(1959)
Carnotite, which is pot~sium ur~ium Vanadate
Carriages and Mounts Testings are described in
contg Radium, was patented as an ingredient of
OP(Ordnance Proof) Manual 30-60( 1957)
pyrotechnic smoke-producing compns
Ref.’ J .DeMent, USP 2995226(1961), 23-4
Carrière(Poudre de). An inexpensive blasting
CarobBean or St John’s Bread. The pods of expl Compn: Na nitrate 63, sulfur 16 & sawdust
Ceratonia siligua, a Leguminosae, rich in sugar 21%
Re/: Daniel(1902), 116
and gum. The gum, called Carob-bean Gum, used
as an emulsifier in ice-cream, lozenge and
Carronade. An iron cannon, designed by Gens
toilet cream manuf (Ref 1), was proposed by Taylor
Melville & Gascoigne, and manuf in the last
(Ref 2) as a waterproofing coating agent for AN
quarter of the 18th century at Carron, Scotland.
grains used in expI compns
It was a short, large caliber piece resembling a
Re/s: l) Hackh’s( 1944), 171 2)W. J .Taylor, USP
mortar. It differed from guns and howitzers in
2654666(1953) & CA 48, 3692(1954)
having a hinge below instead of trunnions. It was
used on ships and shore to throw heavy solid
Care’s Acid or Peroxymonosulfuric Acid, H2SO~.
 c 70

shot at close quarters. The shot could also carry Cartoucherie(Fr). Cartridge factory
incendiary materials. Some of these cannons
were used at the battle of Trafalgar (1805 )(Refs CARTRIDGES
1,2 &3) Cartridge, in a general, consists of an elongated
The Carronade was such a success that one container (called case, shell or wrapper), holding
of its designers (Gascoigne) was invited to a specific item(s) in a fixed position. The item(s)
Russia (1779) to establish cannon plants(Ref 2) which is in the case is complete in itself and it
R e~s: 1) ’’Webster’s New Twentieth Century can be either removed for use outside the container
Dictionary, Unabridged”, The Publishers Guild, or can be used without removal. Cartridge cases
NY( 1947), 262 2)W.Y.Carman, ‘CA History of (qv) filled with proplnts are known as <‘cartridges,
Firearms, StMartin’s Press, NY(1955), 49-50 3) ammunition” and as “cartridges for cartridge
Merriam-Webster’s (1961), 343 actuated devices’ ‘and those which are filled with
expls (such as dynamites) are known as ‘cartridges,
Carry-Over Effect. Under certain conditions, the blasting’ ‘(See also Cartridge Cases)
passage of a detonation wave across the interface Re/.s: l)Glossary of 0rd(1959), 57 & 61 2)
of two different explosives may cause the first Merriam-Webster’ s(1961), 344
expl to t ‘overdrive” the second expl such that its
pressure & deton velocity are higher than normal Cartridges and Cartridge-Actuated Devices(CAD’ s),
for a certain distance until a steady state rate is called Propel I ant Actuated Devices(PAD’s) by
reached. This phenomenon is called the ‘tcarry US Ordnance Corps. Cartridges used in these
-over effect” and is discussed in detail by Pike & devices are called: Power Curttidges (US Navy)
Weir (Ref 6). It is related to detonation by and Gas- Generating, Power-Generating, Gas
influence previously described by several - Producing or Power-Gas Generating Cartridges
investigators (Refs 1 to 5) (literature). A cartridge-actuated device may be
For more info on this subject see Refs defined as a mechanism utilizing pressure
Re/s: I)R.Brinkley & E. B. Wilson, OSRD 1707 supplied by gases evolved on deflagration of a
( 1943) 2) B. L.Hicks et al, JApplPhys 18, 89 I propellant(fired mechanically or electrically in a
(1947) 3)K.P.Staniukovich, DoklAkadN 55, 311 special cartridge) to accomplish or initiate a
(1947) 4)H.Eyring et al, ChemRevs 45, 69-181 mechanical action other than expelling a
( 1949) 5)H.Jones, ProcRoySoc 204, 9-12(1950 6) projectile
H. H.Pike & R. E. Weir, “The Passage of a Deto- Historical. Although the first of these devices
nation Wave Across the Interface Between Two was invented comparatively recently (see Refs 1,
Explosives”, ARE(Armament Research 2 & 3), many types are now known ad their use
Establishment) Report NO 22/50, British is very great especially in avation. One of the
Ministry of Supply( 1950)( Conf) most important uses of CAD’s is for catapults
e jetting pilots and other personnel from rapidly
Cartouche(Fr). Cartridge; round (of ammo); traveling airplanes in cases of emergency
canister (of a gas mask) Prior to WWII when the speeds of military
planes were not very high(up to 400mph) it was
Cartouche ~ bal le(Fr). Ball cartridge possible to escape from a disabled plane by
jumping out. As speeds increased it became more
Cartouche & blanc(Fr). Blank cartridge difficult to separate from the plane by using
muscular efforts, because much quicker action
Cartouche Compltee(Fr). Round of fixed ammunition was required. It was found in Germany shortly
before WWII that quick escape could be achieved
Cartouche d’amor~age(Fr). Ignition cartridge; by ejecting the seat with its occupant by
primer utilizing the pressure of gases developed on
firing a chge of proplnt in a specially designed
Cartouche d’exercise(Fr). Drill (or dummy) cartridge. This cartridge was named
cartridge t CSchleudersitzpatrone “(Ref 6). Many Ger
fighter plane were eventually equipped during
Cartouche sans douille(Fr). Caseless cartridge WWII with seat-ejecting devices. The British
or Cartridge without case. See under Cartridges started in 1945 to add such devices to all fighter
planes with speeds greater than 400mph. In the
 C71

US, although, the study of the emergency escape and thruster were briefly discussed above, under
began as early as 1940, it was not until 1947 Historical. For more info on catapults, see Ref
that the first ejection seat catapult was ll,pp 12-21, 39-42 & 62-4 and Ref 14,pp 6-7; for
standardized. It was designated ‘ %.fI Personnel removers (canopy removers), See Ref 11 ,pp 10-11 &
Catapult”. This was followed by design and 56-61 and Ref 14,P 8; and for thrusters, see Ref
development O{ “MI and M2 canopy removers” Il,pp 83-7 & 97 and Ref 14,p 8. The ejector
or simply removers. AH of these devices were usually serves to eject small masses, such as
mechanically iniated. As this method of initation parachutes(See also Ref 14,pp 8-9 & 146)
was not very satisfactory, an initiationutili zing a C)Special Purpose Devices. Included in this
propInt gas pressure source was developed in category are: cutters(such as for severing
1949 at Frankford Arsn, Philadelphia, Ea. At cables and reefing lines of parachutes)(Ref 1 l,pp
the same time the catapult was redesigned to 5-9 & Ref 14,p 9); releases(for disconnecting the
incorporate the new ~~initiator” parachute from a crash-locator beacon, for
With the advent of the B-52 plane and its suspending and releasingsingle lug bombs, for
requirements for multi-crew, multi-function, pulling safety pins from other CAD’s, etc)(Ref
integrated escape systems, there was developed 14,p 10); exactors(gas-operated firing pin release
( ca 1951ja device which could furnish thrust to mechanisms used in aircraft jettison systems)
position ejection seats and to unlock hatches, (Ref 11 ,pp 64-6 & 94); electric ignition elements
This device became known as thruster and since (dev ic~s designated to replace the firing pins and
1951 several models have been developed(Ref 14, percussion primers used with gas or mechanically
pp 1“2) fired CAD’s (Ref 14,pp 10-11)
The CAD’S (or PAD’s) described in Ref 14 In Ref 14,pp 2-4 are mentioned the following
are arbitrarily divided into the following three other applications of CAD’s: ejection of radio
categories: beacons in the event of a crash, supplying gas
A)Gas-Generating Devices, They may be pressure to operate hydraulic pumps in missiles,
subdivided into “short duration” and “long ‘releasing bombs and jettisoning stores from
duration”. The first, called initiators, are aircraft, ramming of heavy projectiles into the
designed primarily to supply gas pressure breech of howitzers, starting Gatling gun
(during usually Iess than lsec) to operate the rotators and as gas generators for temporarily
firing mechanisms for devices such as catapults. pressurizing hydraulic, air or fuel lines in the
They also may serve as sources of energy for event of prime equipment failure
operating piston devices such as sa/et y-belt In Ref 11 are described the following
releases and sa{ety-pin extractors. For systems additional devices:
where several CAD’s are fired in sequence, butterfly valve cartridge(used to automatically
initiators may contain a ‘t combination train close the butterfly steam valve on a runaway
element’’ (delay element) to delay proplnt ignition shot preventer device of a steam catapult system
for a specific time to permit completion of in an aircraft carrier (Ref 1 l,pp 3-5 and Ref 12 ,p
another operation. The “long duration” devices, 57); /ire extinguisher cartridges(used to release
also caIled “gas-generators” may supply fire extinguishing fluid into the area surrounding
pressure of gas for as Iong as several reins. a jet AC engine on fire (Ref 1 l,pp 22-7); jet
Their principal uses are to spin the gas turbines, engine igniter cartridge(used for relighting a jet
to operate pumps or to operate various missile engine, when the normal air starting ignition
controls(Ref 14,pp 3-5 & 17)( See also Ref 11 ,pp system fails during flight)(Ref 1 l,pp 27-30); lap
56-61, 67-83 & 95) belt release cartridges(used to activate automatic
B)Stroking Devices. They may be subdivided release lap belt after a delay of 3/4 or 2secs
into ‘{open” and t ccIosed” CAD’S, In the first from the time the seat and occupant have been
type (such as in catapults and removers), there is e jetted from a plane in emergency escape )(Ref 11,
separation of piston from cylinder, accompanied PP 30-5); cartridge-vial, life raft(used to actuate
by escape of propfnt gases(See illustration on automatic equipment of a life raft in an
p 6 of Ref 14). In the “closed” types(such as emergency ditching at sea; it consists of a
used in thrusters and ejectors), the piston does cartridge assembled to a vial of compressed
not separate from the cylinder and the gas does carbon dioxide; immersion of device in sea water
not escape into atmosphere,but may be bypassed initiates an elec current which activates an elec
to other CAD’S. Function of catapult remover squib thereby releasing the C02 for inflating the
 C 72

raft(Ref ll,pp 35-8 and Ref 12,p 61); ffrogue 91Anon, ‘tAmmunition General”, TM 9.1900”
gun cartridge(desi~ed to fire a small parachute, ( 1956), 299-304( Cattridge-actuated devices for
c shed e‘drogue”, for stabilizing the flight of aircraft use) 10) F. W. Jarvis & T. B. Rhodes, GerP
seat and occupant after they are ejected from a 1016171(1957) & CA 54, 23334( 1960)(Chges for
plane; this device is part of the Martin-Baker power-gas cartridges. Eg:NG 43.9, NC 27.8,
escape system)(Ref 1 ltpp 43-6 & 94); parachute diethyldiphenyl urea 0.9, cellulose diacetate
harness release cartridge(used to actuate the 26.3, K nitrate 0.9 & petrolatum O. 2%. Rate of
release after delay of 3/4sec from the time of burning 5mm/see) ll)Anon, “Cartridges and
ejection from a plane)(Ref ll,PP 46-8); and Cartridge Actuated Devices”, Bureau of Ordnance
parachute opener cartridge(used to open Pamphlet 2606 US Navy(1959)(Illustrations and
parachute 2secs after ejection)(Ref 1 l,pp 48-50); descriptions for more than 30 types of devices,
another cartridge releases the parachute 3secs used by the US Navy) 12)Glossary of Ord
after ej ection(Ref 11 ,PP 51-3) ( 1959), 57-6 I 13)Anon, ‘tPower Cartridges
In Ref 13 are described various ‘tPower” Handbook”, US Naval Proving Ground, Dahlgren,
cartridges and igniters used by the US Navy. The Virginia( 1961)( Illustrations and some data for
so-called delay cartridges are generally used to numerous types of US Navy’s cartridges and
provide a predetermined time delay to actuate a igniters) 14)Anon, “Ordnance Engineering
release mechanism. The two types described in Design Handbook, Propellant Actuated Devices”,
Ref 13 are used for releasing lap belts in Ordnance Corps Pamphlet, ORDP 20.270, OEHO,
airplanes Duke University, Durham, NC( 1961 )( Comprehensive
Charges used in cartridges for CAD’s are description of principal devices used by the US
either single- or double-base proplnts. For Air Force, including some design techniques)
weaker impetus a BkPdr, based either on K or Na 15)Anon, “Small-Arms Ammunition”, TM
nitrate, may be used; and for very high impetus a 9-1 305-200( 196 1), 53-4 (Cartridge, caliber .45,
composite proplnt( such as based on Amm line-throwing) 16)uS Military Specifications on
perchlorate) may be used (Ref 13) various cartridges (See also Ref 11): a)MIL-C
Re /s: l) ICI of Australia & New Zealand, -25918( l)(CAD’s for AC crew emergency escape)
Australian 100512( 1937) & CA 31, 5166(1937) b)MIL-C-21234( 1), MIL-C-21496A, MIL-C-22648,
(Gas-producing nondetonating charges for use in MIL-C-22652, MIL-C-22656 & MIL-C-22657
piston-operated mechanisms and in blasting) 2) (Cartridge actuators) c)MIL-C-46221, MIL-C
J .M.Helm, USP 2090608(1937) &CA 31,6940 -46237, MIL-C-46241 & MIL-C-46271
( 1937)( Cartridge contg gas-generating materials, (Cartridge for AC ejection seat catapult) d)
suitable for operating lifting jacks, fire MIL-C-25 128(2 )( Cartridge, starter, AC engine)
extinguishers, etc) 3) R. A. Hoffman, BritP e)MIL-C-45408, MIL-C-462OO, MIL-C-46240 &
481639(1938) &CA 32> 6446( 1939)(Self MIL-C-46274(Cartridge, thruster) e)MIL-C
-combustible fuel chges for engine starters) 4) - 18653A, MIL-C-27002B,MIL-C-27019A & MIL-C
R. A.Coffman, USP 2299464, -65 & -66(1942) & - 27029(Cartridge, bomb ejection) f)MIL-C
CA 37, 1849( 1943) (power-generating cartridges - 22244( Cartridge, cable cutter) g)MIL-C-10013 &
used for starting engines) 5)C.D.Pratt, USP MIL-C-12779A(Cartridge, line-throwing) h)
2309978( 1943) & CA 37, 4230( 1943)( Cartridges MIL-C-22362(Cartridge impulse) i)MIL-C
used for starting motors, closing switches, etc) - 13230A(Cartridge, cluster ejection) j)MIL-C
6)E.R.vonHerz, Jr, Explosivst 1954, 64-8 & -25641 (Cartridge, gas generating, solid proplnt,
92-8; CA 48, 14210(1954) [Description of AC & missile, secondary power systems)
development of gas-generating cartridges
(Gasdruckpatronen) in Germany before and during Cart/idge, Aircraft Canopy Remover. See under
WWII. These cartridges were used for starting Cartridge-Actuated Devices
airplane engines (Starterpatronen) and for
e jetting pilots and seats from airplanes Cartridge, Aircraft E iection Seat Catapult. See
(Schleudersitzpatronen)] 7) Frankfort ArsenaI, under Cartridge-Actuated Devices
Philadelphia, Series of Progress Reports on
Development of Cartridge Actuated Devices and Cartridge, Airdox. See Airdox in Vol l,p A117-R
Initiators, beginning in 1954( available at picArsn)
8)F.W.Jarvis & ICILtd, GerP 949726(1956) & CA Cartridge, Aluminum or Aluminum Alloys. See
53, 18488( 1959)(Power-gas cartridges) Refs 2,3,4 & 7 under Cartridge Cases

—. ——.,——
 c 73

CARTRIDGE, AMMUNITION [Patrone(Ger) but proplnt(BkPdf) was introduced loose thru the
-cartridge for small arms or fixed artillery ammo; muzzle of the barrel and the wad and the balks
Kartusche(Ger)-cartridge or bag for separate rammed afterwards. In order to expe~lte loa~ng
-loading ammo; Cartouche(Fr)-generally for all of firearms while on horseback, a paper cartridge
types of ammo; Gargousse(Fr)-for separate loading was invented. At first (ca 1550) it housed only
ammo; Patron(Rus)-for all types of ammo; the BkPdr chge~ but later (ca 1590) cartridges
Oroodiinyi Parton(Rus)-cannon cartridge; contained rh e pdr and the balls. Gwstavus
Cartoccio(Ital) and Cartucho(Span)] . Cartridge, Adolphus of Sweden(1594-1632) introduced the
used in present smooth-bore firearms (shotguns) paper cartridge to his army at the beginning of
consists of a cylindrical pasteboard container the 17th century. This type of cartridge was not
(case or shell) with a metal (generally brass) self-contained because it was not provided with a
base provided centrally with a priming cap. The primer which was unknown at that time. The
case is pard y filled wirh proplnt which is covered first self-contained cartridge was invented in
with cardboard or feh wads. This is foHowed 1826(Frp 3355) and an improved one in 1831
with a load of lead shot and a closing wad. The (EnglP 6196). LeFaucheux invented in 1836 the
erisembIe is called “shotgun cartridge”. These pin-fire cartridge made of cardboard and brass
cartridges are used for combat, guard and combination, something like present shotgun
survival purposes (Ref 15,pp 62-5)(See akso Fig) cartridge. Paper cartridges continued to be used
until about 1850 or even later. The first really
successful metallic cartridge, self-contained and
reasonably moisture-proof, was patented in 1854
by Smith & Wesson. It was used in revolvers, The
first metallic, center-fire cartridge was patented
in 1858 by Morse and adopted in 1865 by the LJS
Army. Foster patented, in 1860, the so-called
“Burnside” cartridge which contained a grease
chamber around the bullet. Williamson patented,
in 1864, the so-called “Teat Cartridge’’(Ref 13,p
7). The latter cartridge is not listed in Ref 2, but
on p & the “Moore Tir Cartridge” is described
US 12.Gage Shotgun Cartridge In 1866 Col(later Gen) Berdan, US Army,
The term “’cartridge” used in present invented a cartridge with a special primer. His
military rifI edt breechIoading firearms is design was adopted by some European nations,
equivalent to the c‘compiete round of ammunition” h the same year Col Boxer, BritArmy, designed a
(See VOI l,p A385-L of Encyclopedia). The different cartridge, known as “Boxer” cartridge.
present military cartridge consists of a cylindrical h was adopted for use in the Snider rifle and its
or bottlenecked metal (brass, or copper, gilding “bottleneck” modification was used in the
metal, aluminum or steel) container(case or shell) Martini-Henri rifle. Descriptions of both Berdan
closed at one end and nearly filled with a chge and Boxer cartridges are given in Ref 2,pp 45-8
of proplnt. A primer is inserted in the perforation After the invention of colloidal NC proplnt
of the closed end(base) of the case and a (1884) and of NC-NG proplnts (1887-8), calibers
projectile(bullet or shell) may be crimped or of small-arms cartridges were reduced and the
force-fitted into the open end(neck) of the case bottleneck design was adopted for most of the
The purpose of a cartridge case(especially rifle, carbine and machine-gun cartridges, leaving
when used in recoil- type cannons) is not only to the cylindrical form for some grenade, small
serve as a container for proplnt, primer and caliber rifles & carbines, revolver, and pistol
projectile, but also to prevent the escape of gas cartridges(See Ref2,pp 21-154 ~d Ref 13~PP
from the rear of weapon on firing the proplnt. 1-17). Cartridges used in artillery ammo are
This function of cartridge as “obturator” is due cylindrical or slightly conical in form
to the expansion of the case against the chamber I) Cartridges, Military, US. Based on usage,
wall under the pressure of burning proplnt(Ref these cartriges may be subdivided into “small
lo,p 128) -arms cartridges” and “artillery cartridges”
Histon”caL In ancient firearms(which were smooth A)Srna21-Arms Cartridges (US) are used in firearms
-bore, muzzle-loaders), no cartridges were used, caliber .60inch or smaller. Based upon type of
 c 74

case, these cartridges may be classified as Depending upon its purpose, small-arms
cente~ fire and rim fire. In a center-fire cartridge, ctges are classified as combat or service and
the primer is located in a small well or pocket, in noncombat or special
the center of the cartridge case head. The rimfire The combat ctges are subdivided into:
cartridge differs in that its priming mist is a)Armor-Piercirzg( AP). See under BULLETS and
located in the flat rim at the base of the cartridge in Ref 15,pp 5,41,44,54 & 56
cas. This rim also serves to properly locate the b)Armor-Piercing Incendiary(APl). See under
cartridge in the chamber of a firearm, and offers a BULLETS and in Ref 15,pp 5,42,54 & 56
means of extracting the cartridge case after firing. c)Arrnor-Piercing incendiary-Tracer(APIT). See
The caliber .22 cartridge(other than hornet) is the under BULLETS and in Ref 15,pp 42,45,54 & 56
only current rimfire type used for military d)BalL See under BULLETS and in Ref 15,pp
purposes(Ref 15,P 5) 36-8,43,46,51,57,58 & 66-70
e)BaZl, Hornet. See under BULLETS and in
Ref 15,p 38
e) Grenade. A special blank ctge used in rifles
assembled with launchers to project A/T, HE,
fragmentation, illuminating, smoke & chemical,
grenades, as well as ground signals(Ref 15 ,pp
50-l)(See also Fig)
-R IMF IRE- CENTER FIRE CASES
CASE g)Incendiary, See under BULLETS and in Ref
RIMLESS 5CMlnlMMCD R4MME0
15,pp 44,58 & 60
Types of US Cartridge Cases h)Shotgun. See a brief definition and an
Center-fire cartridges may be classified as illustration given at the beginning of this section
rimless, semin’mm ed and rimmed Types of and also in Ref 15,pp 44,58 & 60
cartridge cases are illustrated in Fig i)Spotter-Tracer. See under Bullets, Spotter
Illustration of a typical complete round of -Tracer and in Ref 15,p 60
ammunition using a rimless, center-fire cartridge j )Tracer. See under BULLETS and in Ref 15 ,pp
is given in Fig entitled c‘Typical Bullet & 40,45,52 & 61
Cartridge Assembly”, under BULLETS. See alsc The noncombat ctges may be subdivided
illustration of components of US cartridges cals into:
.22, .30, :45, .50 and 12-gage shotgun a)B~ank. See under Bullets, Blank and Dummy

(’) (“ f
/’ :.,
and in Ref 15,pp 39,45,53,62 & 69
‘; /f. ,

u
b)Durnmy. See under Bullets, Blank and Dummy
[4
~/~/\)\;; and in Ref 15,pp 40,45,53 & 62

Ii
#

.4,
,
BP
CALIBER 45
BALL, M1911
. .
CALIBER .?2:
BALL, LONG RIFLE

(
I ‘:

i
~(
c)Frangible.
Ref 15,pp 46-7
d)Higb-Pressure
proof-firing
See under Bullets, Frangible

Test(HP T), A ctge used for

of firearms. It is loaded with a
and in

CAL 16ER 30 ,1’

CAR91NE !\ quantity of proplnt sufficient to produce required
BALL, MI
[ high pressure which might vary from 1000 to
2(L 70000psi. The bullet consists of gilding metal or
{
ql of other material(Ref 15,pp 41,46,53 & 62)
-1. .
e)Line-Tbrow”ng. A ctge, cal 45-70 fitted with a
non-corrosive, primer and proplnt chge which is
~’ ‘ covered with one or more felt wads. It fires a
256-gram projectile attached to a std Navy line
.~
for a min distance 75yds at 30° elevation(Ref 15,
. . “i
pp 53-4)
f)Match. A ctge used for target practice(Ref 15,
.’. , pp 44& 70)
i ‘L< i _. ! —.. ‘&
g)Practice. A ctge listed in Ref 15 ,p 5 without
Ii. +--J -. t. ‘.
12 GAGE SHOTGUN CALIBER 30 BALL, M2 CALIBER 50 BALL, M2 description
h)Sbotgun, Blank. See Ref 15 ,pp 64-5
Components of Typical US Small*Arms Cartridges B)Artillery(Cannon) Cartridges(US) are used in
 c 75

l . .,”,,
.-U9SU*
c .W*, w,,, mm.
o SW
, .c.xvt
‘ +’nmtltl
CARBINE, CALIBER .30 M6 E-um,mr, *9.X
It-wl.m- UFO
..L”)
-X .0. n

..-tV“* Cn.tc,l
,—CM!,,OGI ,.,[
,. mm.wc

u, WC
RIFLE, CALIBER .30: M3 o C.90w.11
,<0”,. .!+ w.” W **
GRCNADE CARTRIDGES a GM.,*
,–<.,,0 “0.m,lw, ,“.=2!

E=iiiaE
LC,ow.c P,LK
,- m , UU-, ~.n
u I*!!I. ‘..,., .,$,*,

Al
b168 MAX TRACER, Ml 6
BALL, Ml .

OUMMY M 13 TRACER, M27

TEST, HIGH-PRESSURE, M 1B
CALIBER .30 CARBINC CARTRl~
— 1.275 ~

BALL, M1911 DUMMY: Ml 921

TIWCER, M26 SIANK. M9

*,,*—ml
US Complete Rounds of Artillery Ammunition

TEST, HIGH-PRESSURE, Ml
CAIJB3R .4S CARTRIDOS3
weapons of calibers larger than 0.60inch.
Calibers and type of ammo used previous to 1960
in camons are listed in Vol l,pp A385-L &
A386-R of this Encyclopedia. To the three types
of ammo: fixed, semifixed and separate-loading
(listed in Encyclopedia and in Ref 7,pp 6-7),
should be added the fourth type called separated
ammunition. This consists of a primed brass or
steel ctge case, a chge of proplnt(sealed with a
closing plug made of asphalt, pressed paper
board or plastic) and a projectile which is not
attached by crimping. Following removal of
shipping plug, the projectile and cartridge case
are loaded into the cannon together, not separately
as in separate-loading ammo(Ref 7,p 6 & Ref 10,
p 130). Having a nonadjustable proplnt chge,
“separated” ammo may be considered a special
type of “fixed” ammo(Ref 10,p 128), but accdg to
Ref 4a,p 113, it is considered to be “separate
loading”. Illustrations of the four above types of
ammo are given in Fig
An artillery cartridge case is usually made
of a special type of brass or steel of spiral
-wrapped multipieced or drawn construction. Its Cartridge, H Recoilless Gun
 C 76

form(usually cylindrical or slightly bottlenecked) 30-3M( 1945) and TM 9=1985=5(1953)

and size conform to that of the chamber of the No info at our disposal about cartridges
weapon in which the round is fired, except for used in other foreign countries
recoilles weapons. The “head” of the case is Refs: l)Hayes( 1938), 26, 376 & 658 2)
relatively heavy in order to provide for firm M.M, Johnson Jr & C. T. Haven, ‘tAmmunition”,
attachment of a primer and a flange or groove to W. Morow, NY(1943), 21-68(Cartridge development
permit mechanical extraction. Cartridges used in from 1600 to the beginning of smokeless proplnt);
automatic cannons have cases with an extracting 69-87 (European military rifle cartridges from
groove instead of a flange or rim. The cartridge 1886 to 1943); 88-112(US military rifle & carbine
case in recoilless weapons is perforated in a cartridges from 1886 to 1943); 113-54 (Smokeless
manner to allow sufficient quantity of proplnt proplnt sporting-rifle cartridges); 15 5-88( Pistol &
gases to escape into the weapon chamber and out revolver cartridges); 189-208( Shotgun cartridges
of the breechblock into rhe atmosphere to or shells) and 371-4( Cartridge designations) 3)
counteract weapon recoil. The interior of J. Newman, “The Tools of War”, Doubleday,
recoilless-weapon cartridge cases contain a Doran & Co, NY( 1943), 44-5 4) Anon,
liner(of paper, rayon or plastic) that serves to “Ammunition Inspection Guide”, TM 9-1904
cover the perforations, thus preventing the (1944), 180-220( Small-arms cartridges); 446-84
entrance of moisture and spilling of the proplnt (Artillery cartridges) 4a)Anon, “Ammunition
grains(Ref 10 ,p 128)( See Fig bottom of p C 75) General”, TM 9-1900 1945),pp 11 l-15(Se,e also
Calibers of cartridges used ca 1950 in the Ref 10) 5)0hart( 1946),65,74 & 78-85 (Small-arms
US artillery ammo are listed in Ref 7 cartridges); 171-83 (Arti11ery cartridges) 6)
For larger caliber weapons, such as 155-mm G. M. Barnes, “Weapons of World War II”,
guns and howitzers, proplnt charges ate contained VanNostrand,NY( 1947), 42-3(SmaH-atms cartridges)
in bags( see under Cartridge Bags) 52-3(Recoiless-guns cartridges) 7a) Anon,
II)Cartridges, Military, NATO, Small Arms. The * ‘Small-Arms Ammunition”, TM 9-1990( 1947), 1-11
following types of North Atlantic Treaty C%53-153 7)Anon, “Artillery Ammunition”, TM
Organization cartridges are described in Ref 15,pp 9=1901(1950), 4-6, 69-160 & 174-201 7a)Anon,
47-50: “Ammunition”, US Military Academy, West Point,
7.62mm NATO, AP, M61; 7.62mm NATO, Ball, NY(1950), 3-8, 17, 26-7 & 31-46 8) Anon,
M59; 7.62mm NATO, Ball, M80; 7.62mm NATO, ‘ ‘Fundamentals of Small Arms”, TM 9-2205
Test, High Pressure, M60; 7.62mm NATO, (1952), 28-31 & 34 9)EncyclBritannica ~ (1952),
Tracer, M62; 7.62mm NATO, Blank, XM82 and 824( Artillery cartridges); 20( 1952), 8 10(SmaH
7.62mm NATO, Dummy, M63 -arms cartridges) 9a)PATR 2145( 1955),p RUS 2
No info at our disposal on cartridges used (Ammanition)(Conf) 10)Anon, ‘ ‘Ammunition
by NATO in artillery ammo, however a constant General”, TM 9-1900(1956) 81-94( Small-arms
effort to standardize is being conducted(Ref 18) cartridges); li8-30(Artillery cartridges)(See also
III)Cartridges, Mi I itary, Argentina@ Calibers of Ref 4a) 10a)ORDP 20-244(1957), f cArtiHery
ammo used ca 1960 are Iised in VO1 l,P A478-L Of Ammunition”, Seen 1 ll)PATR 2510( 1958),pp
this Encyclopedia Ger 25-7 & 177-80(Ger cartridges of wWII) 12)
IV)Cartridges, Military, Belgium. Calibers of Glossary of Ord( 1959), 57-61 13)H.C.Logan,
ammo used ca 1961 are listed in VO1 2 of this “Cartridges, A Pictorial Digest of Small-Arms
Encyclopedia under Belgian Explosives, Ammunition”, Stackpole, Harrisburg, Pa( 1959)
Ammunition, etc 14)W.H. B. Smith, “SmalI-Arms of the World”,
V)Cartridges, Military, France. NO info at OUr Stackpole, Harrisburg, Pa(1960), 699-703 15)
disposal. Anon, “Small-Arms Ammunition”, TM 9-1305-200
VI)Cartridges, Military, Germany. Brief description ( 1961), 2-10, 22-4 & 36-70 16)Anon, “Index of
of cartridges used during WWII are given in Ref Specifications and Standards”, Supplement Part 1,
11. For more detailed info see TM 9-1985-3 Alphabetical Listings, Armed Forces Supply
(1953) Support Center, Washington 25, DC, Sept 1961 ,pp
VII) Cartridges, Military, Italy. Descriptions of 107-1 1(US specifications for cartridge cases and
cartridges used during WWII are given in TM cartridges for small-arms and artillery ammunition)
9.1985-6(1953) 17)Anon, “Index of Technical Manuals, Technical
VIII)Cartridges, Military, Japan. Descriptions of Bulletins, etc”, Dept of the Army Pamphlet No
cartridges used during WWII are given in OPNAV 310-4, Washington 25, DC, April 1962,p 998
 c 77

[Technical bulletins (TB’s) describing cartridges Cartridge Belt, A leather or fabric band with
calibers 40,75,81,90,105 & 280mm] 18)A.B. loops or pockets for carrying cartridges or
Schilling, Picatinny Arsenal; private communication cartridge clips. It can be worn around the waist
(1962) like a belt or suspended from the shoulders, In
the Iatter case it is called bandoleer
Cartridge, Artillery. See under CARTRIDGE, Re/s: I)Glossary of Ord(1959), 31 & 57 2)
AMMUNITION Merriam-Webbter’s( 1961)

Cartridge Bags. Propellant charges in “separate Cartridge, Belt. A fabric or metal band with
-loading ammunition’ ‘(See Ref 7)(such as used in loops for carrying cartridges that are fed from it
guns and howitzers caliber 155mm and higher) are into a machine gun or other automatic weapons
contained in bags made of cloth which does not Refi Glossary of Ord(1959), 57
leave any residual smoldering fragments or ash in
the bore after firing. Smoldering fragments might Cartridge, Blank, An item consisting of a ctge
ignite unburned products resulting from combustion case, primer and smokeless proplnt or BkPdr, but
of the proplnt(mostly CO) causing a “flareback” no projectile. It is used in training in signaling,
(Ref 1,2,4& 5).Silk cloth was used in the US and in saluting(See also under BTJLLETS and
before WWII, but when silk became unavailable under CARTRIDGE AMMUNITION)
(during the war) it was replaced by mohair. In Re/: Glossary of Ord(1959), 57
Germany they used successfully cotton treated 1
with a soln of NC. In GtBritain, Dreyfus(Ref 3)
Cartridge, Blasting. Blasting expls(such as
patented a cartridge cloth made of regenerated
dynamites) are usually furnished in cylindrical
cellulose impregnated with guanidine or one of
containers, called wrappers or shells consisting
its salts, especially Gu metaphosphate
of paraffined paper. These not only serve to
At present acrylic cotton fibers are used in
protect the expl from moisture, but they also
US cartridge bags(Ref 6 )( See also Fig) facilitate handling, storage and loading into
bore holes. The ensemble: ie container plus charge
is called “cartridge”. Cartridges manufd by the
DuPont Co are subdivided into “small’‘(diam
CHARGE. PBOPH.LIMG M3 (GREENBAG) 11/e, 11/4, 11/2, 13/4 & 2“ and length 8“) and
“large’ ‘(diam 4, 4X, 5 & 7“ and length 16 or 24”).
The largest cartridge which can be shipped under
ICC(Interstate Commerce Commission) Regulations
~. ,~ ,M*X
is 501bs, total wt, with a maz diam 12” & a max
CHARGE PROPELLING M4A1 (WHITE 6AG! length 36”(except for dynamites contg less than

.,-,,
,..-
,- w,,, ,.,
—. .. . ...
.—. -,.-r, -... ~~—
!!
-+— 11
10% NG, in which. case there is no litpitation
length)
on

!iiiilii~
,- ,.-. For dynamite cartridges having a diam of
.... . . . ~17F&&$lV@fiL?~I~]~ fiJ~T?&~@jJ ‘2“ or less, the most common type of container is
*X,. i-!
.-..’$$ ., .
... .. ... s made from spirally wound Manila paper which is
575 IN MAX + impregnated with paraffin. For very hydroscopic
CHARGE, PROPELLING Ml 3 expls, the container is dipped, after filling it with
Re/.s.’ l)Hayes(19s8), 34-5 2)Anon, “Ammunition expl,into a bath of molten paraffin. For cartridges
Inspection Guide”, TM 9.1904(1944), 507-10, larger than 2“ in diam, a spiral wound, glued
526-7 & 539-41 3)H.Dreyfus, Britp 569040(1945) & paper shell is used. This type of cartridge is
CA 41, 4929(1947) 4)Oharr( 1946), 184-91 5)Anon, waterproofed by spraying with molten paraffin.
“Artillery Ammunition”, TM 9=1901(1950), 337-52 Some powder-type dynamites are packed in
6) Anon, “Ammunition General”, TM 9-1900(19>J), strong Manila paper bags, making 12.5-lb chges.
130-1 “l-his type of loading facilitates the pouring of
expls into small diam boreholes
Cartridge, Ball. A cartridge in which the For some types of blasting, BkPdr is still
projectile is of the ball type(See also under in use. The DuPont Co manufactures pressed
BULLETS and CARTRIDGE, AMMUNITION) cylindrical pellets ca 2“ long and lfi to 2“ in diam,
Re/: Glossary of 0rd(1959), 57 provided with a central hole 3/ e“ in diam. Four
 iC 78

of these pellets are wrapped in red shell paper to cartridge case is given in Ref 36,p 231. Cartridge
form a cartridge 8“ long. The cartridge is then cases used in ammunition are usually cylindrical
dipped in paraffin or bottlenecked in shape and can be of paper,
Some types of work, notably seismic cardboard, parchment, metal, cloth or combustible
prospecting, require a means of joining dynamite material. The most common material formerly used
cartridges together to make a continuous column for cartridge cases for military purposes was
for loading into boreholes. ne couPling devices brass(Refs 1,16 & 22 and some Refs, under
are known as cartridge coupIers and the type CARTRIDGE, AMMUNITION)
manufd by the DuPont Co is called “Fast-Coupler” As brass was a critical material during WWII,
(Ref 3,P 56) in Europe, the Germans started to use steel and
It should be mentioned that after WWII, when many cases were manufd from this material(Ref
large quantites of scrap, cast TNT were available 28a,p Ger 27). As steel proved to be a
as surplus material, some blasting cartridges for satisfactory material! steel cases are now made in
use in ‘ ‘strip mining” were made by filling other countries including US(Refs 8,9,10,11,13,
cylindrical cardboard containers(3-4” in diam and 15,1 7,21,24a & 28). Other metals such as Al and
ca 3ft long) with lumps of TNT. For initiation of its alloy s(Refs 2,3,4 & 7) or Zn-Cu alloy s(Ref 6)
TNT, a cartridge of dynamite provided with a have also been tried. The possibility of using
blasting cap was inserted in the upper (open) s intered iron cartridges ~as been investigated at
part of each cardboard cylinder(Ref 6) Frankford Arsn, Philadelphia(Ref 20), but further
Compositions of expls used in blasting work is required. Plastic cartridge cases are
cartridges are given under Blasting Explosives described in Refs 12 & 27
Some special cartridges, such as Airdox, Illustrations of typical metallic cartridge
Cardox, Chemecol, Hydrox and Sheathed Cartridges cases are given under CARTRIDGE, AMMUNITION
are described separately(See aIso Ref 5) Since metallic, artillery cartridge cases are
Cartridge-packing machines for dynamites expensive, they are usually recovered after firing
are briefly described in Refs 1 & 2 and then shipped back for reprocessing or
Re/s.’ 1 )Naofim, NG( 1928), 167-73 2)Stettbacher salvaging of the metal(Ref 36). A non-metallic
(1933), 302, & 304-9 3)Blasters’Hdb( 1952), 47, cartridge case which would burn completely
54-7, 65, 70 & 79-82 4)A.Izzo, *’Manuale del during firing of a weapon would be an advantage
Minatore Esplosivista”, Hoepli, Milano(1953) 5) to all troops. Such a cartridge, now known as
Taylor & Gay(1958), 123-44 & 16o 6)G.D.Clift, <‘combustible case”, was first deveLoped during
Chemical Center, Edgewood, Maryland; private WWII in Germany(Ref 25). The case was made
communication(1962) from nitrated pulp. Combustible cases are also
manufd in the US, but the compn of their wall
Cartridge, Bomb Ejector. See under Cartridge material is either not revealed or classified
-Actuated Devices (Refs 26,29,31,32,33,34, & 36). The so-called
“cartridge without case” or “caseless cartridge”,
Cartridge, Butterfly Valve, See under Cartridge invented in France(Ref 24) does not seem to be
-Actuated Devices promising
One disadvantage of a combustible case is
Cartridge, Canister. A ctge assembled with a that it does not perform the fundtion of sealing off
canister the rear end of the gun tube, which prevents
leakage of the high-pressure propelling gases.
Cartridge, Canopy Remover. See under Cartridge This function is achieved in a cartridge case
-Actuated Devices consisting of a short meral base to which is
attached a combustible cylinder. This cartridge
Cartridge, Cardox. See Cardox case is called “partially combustible’‘(Ref 36,PP
232 & 234)
Cartridge Cases. It has been mentioned under R e{s: l)M.Soto, Memorial de Artileria(Feb & Aug
CARTRIDGE, AMMUNITION, that the case 1930) [Translation from Span in MAF 12, 219-46
serves as a container for proplnts and aiso for (1933)] (Manuf of cartrklge cases) 2)
sealing off the rear end of the gun tube, during Aluminium Industrie AG, BritP 455761( 1936) & CA
firing, against the back pressure of propelling 31, 2578( 1937)( Cartridge cases for military
gases. More detailed description of functions of a purposes made of AI-alloy which is coated with
 c 79

oxide produced by anodic oxidation) 3) methods used in manuf of steel artillery ctge
Schering-Kahlbaum AG, BritP 466320(1937)&CA cases) 22)Papers presented at the Cartridge
32, 782(1938)(Ctge cases of Al or Al-alloy coated Case Committee Meeting, Held at NOL, White
with AIF3 or Al phosphate) 4) Aluminium Ind AG, Oak, Md, Ordn 40, 535-44( 1955)( Discussions on
BritP473732(1937 )& CA 32, 2897 -8(1938 )(Cases various methods of manuf artillery ctge cases)
from Al-alloy, being improved by heat treatment) 23)L.Pourquie, MAF 29, 333-45( 1955)( Th40rie de
5)S.R..Carson, USP 2111167(1938) & CA 32, fonctionnement des douilles au tir), translated by
3618( 1938)( Sma11-arms ctge cases are covered with Dr G. Loehr as “Theory of the Functioning of
a strongly adhering dry lubricating and protective Cartridge Cases During Firing”, PicArsn
coating such as a mixt of pyroxylin and very Translation No Q 1956) 24)M.Linyer de la Barb6e,
finely divided amorph graphite) 6)K.Staiger, USP MAF 29, 801-16( 1955)( Cartouches saris douilles),
2190536(1940) & CA 34, 4051( 1940)(Ctge cases of translated by Dr G. R. Loehr as ‘tCartridges
Zn-Cu alloys) 7)J.Korpium, USP 2196018(1940) & Without Cases”, PicArsnTransIation No 10(1957).
34, 5045( 1940)( Ctgecases ofoxide-coated AIor Critical evaluation of the idea of “caseless
Al-alloy) 8)H.R.Turner, IronAge 149, No 12, cartridges” by Dr. H.Schmager is given on pp 16-2
54-5(1942) & CA 36, 3765( 1942)( Artillery ctge [Linyer de la Barb~e investigated the possibility
cases made of steel) 9)C.D.Coxe, USP 2286064 of eliminating cartridge cases by directly combining
(1942) & CA 36, 6996( 1942)(Ctge case manufd by a proplnt with projectile. He examined various
special process from low-carbon steel contg some possible solns and selected that of molding
Cu) 10)R.B.Schenk, IndHeating 10, 639-40, 642, solve ntless proplnts(of standard US accelerated
644,646,648,650,652,654,656 & 658(1943) & CA combustion type) into a hollow multiperforated
38, 1197(1944)(A brief history of the development cylinder, which had an aperture at the forward end
of steel ctge cases) 1 l)W.Hesse, Wehrtech- corresponding to the rear half of the projectile.
Monatsh 47, 259-69(1943) & CA 39, 4038(1945) This system has some advantages but its
(Development of Cu-plated steel ctge cases) 12) disadvantages are such that Dr:H.Schmager of
J .E.Rothrock, USP 2340695(1944)&CA 38,4448 Essen, Germany considers the idea as utopian]
(1944)(Ctge cases made of synthetic molding 24a)P.H.Butdett, “Ordn 42, 195-7( 1957)(A review on
materials such as resin-lignin fiber mixt) 13) the progress made in the development of steel
H.R.Turner, Metallurgic 29, 281(1944) & CA 40, ctge cases for small arms) 25)Drs H. Leuning,
7126(1946)(Manuf of steel ctge cases carried out H. Walter & p .Miiller, “Manufacture of Combustible
in 5 stages with several intermediate annealing) Cartridge Cases from Nitrated Pulp”, PicArsn
14)A.M.Cohn, USP 242954(1947) & CA 42, Translation No 16 by Dr G. R. Loehr(1957) 26)
764( 1948) [A ctge case shaped Iike a shotgun S. Axelrod & G.Demirrack, PATR 2454(1957)
shell is coated on the inside with a flash compn (Development of new formulations for combustible
(such as a mixt of aromatic nitrocompd and an ctge cases) (Conf) 27) Anon, Ordn 42, 474(1957)
oxidizer), and then loaded with grains(O.24° diam (Plastic ctge case) 28)Ahon, Ordn 42, 1029
& 0.26” long) of colloided smokeless proplnt. ( 1958)(Steel spiral-wrap ctge case) 28a)PATR
The flash compn causes uniform ignition tbuout 251 O(1958),pp Ger 25-7(Ger cartridge cases) 29)
the entire ctge ] 15) C. C. Fawcett et al, USP S. Axelrod & V. Mirko, PATR 2478( 195t3)(Improved
246285 1(1949) & CA 43, 3770( 1949)( Manuf of formulations for combustible ctge cases)(Conf)
cases from carbon fine-grained steels by cup and 30)G.Demitrack, PATR 2522( 1958)( Combustible
draw-case forming techniques) 16)Encycl- primer for use in combustible ctge case)(Conf)
Britannica 2(1952), 787( Manuf of ctge cases) 17) 31)S.Axelrod et al, Propulsion Application
K. T. Norris, Ordn 38, 930-4( 1954)( The steel ctge Section,Progress Report PAS Rept NO 101,
case) 18)W.N.King, Ordn 39, 49-52(1954) PicArsn, (Feb 1960)(Research and development of
(Manuf of steel ctge cases) 19)R.R,Gomez, combustible ctge cases)(Conf) 32)E.Wurzel,
Ordn 39, 491-94( 1954)( The spiral-wrapped case) PAS Rept No 102(March 1960)(A survey of
20) J. P. Scanlan, “Sintered Iron for Car~ridge Cases”, methods of prepn of combustible ctge cases) (Conf)
Frankford Arsn Rept No R-1180, Project TSI-46 33)Anon, C & EN 38, 63(Dec 12, 196@(A new
( 1954)(Attempts to fabricate cal .5o ctge cases combustible ctge case has been developed by
from high density sintered iron cups by the cold Armor Research Foundation; compn is not given)
drawing process gave rather promising results, 34)S.Axelrod et al, PAS Rept No 121, PicArsn
but further work is required) 21 )L.Schiller, Ordn ( July-Aug 1961)(Rept on progress of work on
40, 358-61 (1955 )( Comparison of heat-treating combustible ctge cases)(Conf) 35)US Milit~y
 C 80

Specifications: MIL-C-203671, MIL-C-46236, Sensitiveness of Explosives. Tests conducted at

MIL-C-46275 and MIL-C-46276 36)Gen W.K. the USBurMines with 40 and 60% gelatin- and
Ghormley, Ordn 47, 231-4 (1962 )( Combustible and ammonia- dynamites in ctges 7/8, 11/4 and 11/2”
partially combustible cartridge cases) diam, showed that both the rate of deton and the
gap test values decreased with a decrease in
Cartridge Cases, Tests of aredescribedin OP diam. It was found also that more misfires took
(ordnance Proof) Manuals 8-1 6(1942) and 10-50 place in small boreholes than in larger ones. As
(1957) the proportion of paper wrapper to explosive
itself is greater in smaller diam ctges, more
Cartridge, Catapult. See under Cartridge-Actuated poisonous gases such as CO are formed in
Devices boreholes. Both economy and safety are
decreased by the use of 7/8” diam ctges and for
Cartridge, Center-Fire. See under CARTRIDGE, these reasons they are not recommended for use.
AMMUNITION It is considered that the min diam should be 1%”
R ef: S.P .Howell & J .E.Crawshaw, USBurMines
Cartridge, Chemecol. See Chemecol Report of Investigation RI 2436(1922)

Cartridge, Clip. A sheet-metal item intended to Cartridge, Drogue Gun. See under Cartridge
hold together a number of cartridges at their Actuated Devices
bases in order to facilitate rapid loading into the
magazine of a rifle or pistol Cartridge, Dummy. See under CARTRIDGE,
Refs: I)Funk & Wagnalls, C‘New Standard AMMUNITION
Dictionary”, NY (1958), 410 2) Glossary of Ord
(1959), 72 Cartridge, Ejection Seat Catapult, See under
Cartridge-Actuated Devices
Cartridge Cloth. See Cartridge Bags
Cartridge, Engine Starter. See under Cartridge
Cartridge, Combustible. See Refs 25,26,29,30,31, -Actuated Devices
32,33 & 34 under Cartridge Case
Cartridge, Exactor. See under Cartridge-Actuated
Cartridge Counts. The number of dynamite Devices
cartridges, 114x8” contained in a 501b box. This
number is for “DuPont Gelatin” 85-96, for Cartridge, Full. A ctge contg a chge of proplnt
“Gelex” Nol 110 and for “Doubel E” or “tMonobel intended to produce full service velocity of a
E“ 205ctges weapon
Ref: Blasters’Hdb(1952), 60,64 & 70 Re/: Glossary of 0rd(1959), 58

Cartridge Couplers. See under Cartridge,Blasting Cartridge, Gas-Generating. See under Cartridge
-Actuated Devices
Cartridge, Cutter. See under Cartridge-Actuated
Devices Cartridge, Grenade. See Cartridge, Signal(for
Grenade Launcher)
Cartridge, Delay. See under Cartridge-Actuated
Devices Cartridge, Grenade(Rifle and Carbine). See under
CARTRIDGE, AMMUNITION and US Specification
Cartridge, Depth Charge Projector. A ctge contg JAN-C-746
proplnt used to project a depth chge from a
weapon such as a Y-gun, which is a we-barrel Cartridge, High Pressure Test of. See under
device, shaped like the letter Y. It throws depth CARTRIDGE , AMMUNITION
chges to either side of the stern of a vessel on
which rhe gun is mounted Cartridge, Hydraulic. A device consisting of a
Re/: Glossary of Ord(1959), 58 & 322 number of small hydraulic rams, used for
disintegrating coal or rocks
Cartridge Diameter Effect on Strength and Ref: Funk & Wagnalls, “New Standard
 C81

Dictionary”, NY(1958), 410 in an electrically primed ctge case together with a

small chge of proplnt
Cartridge, Hydrox. See Hydrox Cartridge R efs: I) Anon, “Military Pyrotechnics”, TM
9=1981(1951) 2)Glossary of.0rd(1959), 60 3)
Cartridge, Igniter for. See under Cartridge US Specifications MIL-C-1 1232, MIL-C-1 1233A,
-Actuated Devices and “Power Cartridge MIL-c-12910 & MIL-c-13086
Handbook”, US Naval Proving Grounds, Dahlgren,
Va(1959) Cartridge, plastic. See Refs 12 & 27 under
Cartridge Case
Cartridge, Illuminating. A pyrotechnic device
used to provide illumination for reconnaissance, Cartridge, Pyrotechnic, Any pyrotechnic item in
observation, bombardment, lan ding, and projectile the shape of a cylinder may be so called. This
firing, It usually contains a flare and a parachute might include illuminating cartridges, such as
for suspension in air fhres(with or wo parachutes), photoflash,
Refs: I) Anon, “Military Pyrotechnics”, TM signals for pyrotechnic pistols and projectors,
9-1981(195 1), 5 & 31 2)Glossary of 0rd(1959), 155 slick marker and smoke cartridges
3)US Military Specification MIL-C-12926A Refs: l) J. Goldenson & C. E. Danner, C & EN 26,
1976-8(1948) & CA 42, 6115-16( 1948) (Description
Cartridge, Incendiary. A ctge contg a projectile of some Ger, Ital & Japanese pyrotechnic
designed to produce an incendiary effect at the cartridges used during WWII) 2) Anon, a*Military
target Pyrotechnics”, TM 9-1981 (1951), 5, 31-62, 72-6,
Refs: 1 )Glossary of 0rd(1959), 59 2)US Military 104-44 & 146-59 3)Anon, “Ammunition GeneraI”,
Spec MIL-C-1316(Cartridge, incendiary, caliber TM 9-1900(1956), 193-212 4)US Military
.50) Specifications: MIL-C11232, MIL-CI 1233A,
MIL-C-11765B, MIL-C-12825A, MIL-C-1291O,
Cartridge, Initiator. See under Cartridge-Actuated MIL-c-12926A, MIL-C-13086, MIL-C-18539(2),
Devices MIL-c-45 115 and MIL-C-46411

Cartridge, Jet Engine Igniter. See under Cartridge Cartridge, Release (Aircraft Safety Lap Belt).
-Actuated Devices See under Cartridge-Actuated Devices

Cartridge, Lap Belt Release. See under Cartridge Cartridge, Remover. See under Cartridge-Actuated
-Actuated Devices Devices

Cartridge, Life Raft Vial. See under Cartridge Cartridge, Rimfire. See under CARTRIDGE,
-Actuated Devices AMMUNITION

Cartridge, Line Throwing. See under Cartridge Cartridge, Sheathed. See under Sheathed Cartridge
-Actuated Devices
Cartridge, Signal (for Grenade Launcher). Some
Cartridge, Paper. See under CARTRIDGE, pyrotechnic ground signals are projected by means
AMMUNITION of grenade launchers attached to rifles or carbines,
using special blank cartridges. The same method
Cartridge, Parachute Harness Release. See under of propelling may be used for smoke rifle grenades
Cartridge-Actuated Devices Ref: Anon, “Military Pyrotechnics”, TM 9=1981
(1951), 111”22
Cartridge, Parachute Opener. See under Cartridge
-Actuated Devices Cartridge, Sintered Iron. See Ref 20, under
Cartridge Cases
Cartridge, Photoflash. A device for use in
connection with aerial photography at low altitudes Cartridge, Steel. See Refs 8,9,10,11,15,17,21,
100 to 5000ft, during reconnaissance missions. It 24a & 28, under Cartridge Cases
consists of a photoflash chge and delay fuze
assembled in a case which, in turn is assembled “Cartridge Strength”. The term “strength”
 C 82

refers to the energy content of an expl which in Cartridge, Y Gun. See Cartridge, Depth Charge
turn determines the force and power it deveIops Projector
and the work it is capable of doing. The strength
of a straight NG dynamite is usually expressed in Cartridge, Zinc. Copper Alloy. See Ref 6, under
percent of NG by wt. The dynamite contg 40% NG CARTRIDGE, AMMUNITION
is considered as a “ standard” and its strength, as
detd by ballistic mortar, serves for comparison Carvone(l-Methy l-2-oxy-4-isopropy lene-A=-tetra-
with other dynamites. A dynamite contg 20% NG, bydro-benzene or 6, 8-p-menthadien-2-one),
when tested by ballistic mortar, does not give value CO-CH
of strength equal to 50% of 40% dynamite, but / ‘\cH.c/cH’
somewhat higher. This is because some of the “c”cNcH-cH/ >CH ; cO1 liq’ bp Ca
80% of other ingredients of 20% dynamite are also 2 2
contributing to the energy delivered by the expl.. 225°; constituent of the oils of caraway, dill and
When the percentage of NG is increased to 60%, cumin(Refs 1 & 4)
it does not mean that its strength is increased Harries et al(Refs 2 & 3) claimed to prepare
3-times as much as that of 20% dynamite. This is the diozonide and the diozonide peroxide of
because the energy gained by increase of NG carvone. Their structures were ,not detd. The
content, is partially lost due to the decrease in diozvnide was obtained as a yel oil on treating
other ingredients, some of them. contributing to carvone in CC14 with ozone, followed by
the strength purification with petr ether. It deconpd on standing
It is often desirable to know how the strength with format ion of formaldehyde. Further treatment
of a single cartridge rates in comparison with the of diozonide with ozone yielded diozonide
strength of a ctge of the same dimensions contg peroxide, which exploded by itself after standing
standard dynamite. This is known as t Cartridge for several hrs in a freezing mixt. It expld
strength”, “bulk strength” or “volume strength”. almost instantly when treated with warm w or
It is detd by balIistic mortar tests when rubbed with a glass rod
It should be pointed out, that two dynamites Re/s: l)Beil 7, 153, (101) & [128] 2)Beil 7,
of the same strength do not necessarily produce ( 101) 3)C.D.Harries, “Untersuchungen fiber das
the same blasting action in mines, quarries, etc. Ozon”, Springe~, Berlin( 1916), 445 & 450
This is due to the fact that props other than 3)Hackh’s(1944), 173
strength, particularly density and velocity of
detonation, have a distinct influence on their Case-Bonded Propellant. A rocket proplnt charge
performance prepd by casting directly in the chamber of
Re/s: l) Blasters’Hdb( 1949), 47 & 49 2) Blasters’ rocket motor (See under CAST PROPELLANTS)
Hdb(1952), 49
Case, Cartridge. See Cartridge Cases
Cartridge Tests, For description of various
tests to which cartridges are subjected for Cased Charges or Cased Explosives. Any expl
acceptance and, subsequently for surveillance material confined in a case, which can be metal,
and grading are described in: plastic, cardboard, etc, may be so called. There
R e/s: Anon, <‘Test Methods for Small-Arms is no book on this subject, but a number of
Ammunition”, Ordnance Proof Manual ORD reports, mostly of British origin. The confidential
)d608=pM, Frankford Arsenal, Philadelphia, Pa references listed below were not used as sources
(1945) 2)Anon, C‘Small-Arms Ammunition”, TM of info(Comp with Sheathed Explosives)
9=1990(1947), 40-50 3)Anon, “Artillery R efs.’ l) GtBritAdvisoryCouncil, “Cased Charges,
Ammunition”, TM 9-1901(1950) 4) Anon, “Arms Casing of Different Materials, Mild Steel, Cast
and Ammunition Testing”, Ordnance Proof Iron, Lead and Aluminum”, AC 460( 1944)( Conf)
Manual, OPM 10-50, VOI 1(1957) 2)Anon, Safety in Mines Research Station,
Buxton, England, “Cased Charges, Fragmentation’1
Cartridge Thruster. See under Cartridge-Actuated D41 ( 1944), OTIA No 7149(Conf) 3)G.Ward et al,
De.~;ces “Evaluation of the Effectiveness of Various
Types of Cased Explosives”, Instrumentation
Cartridge-Vial, Life Raft. See under Cartridge Report 1134-57, PicArsn(1957)(Conf)
-Actuated Devices
 C83

“Case Histories of Accidents in the Chemical R e/s: l)EncyclBritannica 4(1952), 961-2 2)

Industry”. Title of the book published by the Merriam-Webster’s( 1961), 346
Manufacturing Chemists Assoc, Inc, Washington
9, DC, Vol 1(1962), 192pp Case-Shot. See Canister

Casein or Caseinogen. A white phosphoprotein Casse-Blocs "Celtite" A shaped-charge

occurring as a colloidal suspension in milk. It (charge creuse in Fr), consisting of AN 74.6 &
can be pptd by heating milk with an acid or by 20/80-Pentolite 25.4%, manufd by the Soci4t6
other methods. Casein is the principal Anonyme d’Explosifs Industrials at Dijon, France.
ingredient of cottage or other cheeses. It is also The chge is used by placing it directIy on a rock,
used in manuf of plastics, paints, paper, tree, etc
synthetic fibers, etc Re/: A. Izzo, “Manuale del Minatore
Re /s: l) E. L. Tague, “Casein, Its Preparation, Esplosivista”, Hoepli, Milano(1953), 153 & 156
Chemistry and Technical Utilization”, Van
Nostrand, NY( 1926) 2)Ullmann 3(1929), 110-15 Castan (Explosif de) or Poudre Végétale,
(not found in new edition) 3)Thorpe 2(1938), 411-17 patented in 1884 consisted of Knitrate 48, K
4) H. Hadert, “Casein and Its Uses”, Translated chlorate 20, S(flour) 20 & sawdust 12%
from the Ger, ChemPubgCo, NY(1938) 5)E. Refs: l)Cundill( 1889) in MP 5, 305(1892) 2)
Sutermeister & F. L. Browne, ‘ ‘Casein and Its Daniel(1902), 117 & 782
Industrial Application”, ACS Monograph No 30,
Reinhold, NY( 1939) 6)Kirk & othmer 3(1949), Castan (Poudre Plate de). BkPdr in the form of
225-36 7)M.Beau, “La CastSine”, Dunod, Paris parallelipipedes measuring 10 x 10 x 2mm,
(1952) 8) J. R.Spellacy, “Casein, Dried and , formerly used in French cannons of calibers 75 &
Condensed Whey”, Lithotype Process Co, San 85mm
Francisco, Calif( 1953) 9)US Military Specification% Ret: Daniel(1902), 117
MIL-C-11532
Casteau(Explosifs de). safety expls patented in
Casein, Nitration. Accdg to Johnson & Belgium in 1899 and manufd by c‘La Poudrerie de
Kohmann(Ref 3), the first attempt to treat casein Casteau”. The No 1 formulation consisted ~f AN
with-nitric acid was made in 1885 by Nencki & 90 & nitrodextrin 10%, whereas the No 2 variety
Sieber(Ref I) who obtd p-nitrobenzoic acid contained 1 to 5% rosin added
instead of nitrated casein, as expected. The 2nd Re/: Daniel(1902), 117
attempt was made by von Fiirth(Ref 2) who
nitrated not only casein, but also white of egg Castellanos(Poudres), Two types of dynamites
(albumin) and horn were used at the end of the 19th century: a)NG+ NB +
Re/s: l)M.Nencki & N.Sieber, Ber 18, 394(1885) fibrous material + pulverized earth and b) NG + K
2)0.von Fiirth, ‘ ‘Einwirkung von Salpetersaure or Na nitrate + picrate + sulfur + carbon +
auf Eiweissstoff”, Habilitationsscbift, Strassburg incombustible salt insol in NG(such as Zn, Mg or
(1899)(Not available at PicArsn Library) 3) Ca silicate, Ca oxalate or Zn carbonate. The
T. B. Johnson & E. F. Kohmann, JACS 37,1864-5 recommended compn of latter type consisted of :
(1915) NG 40, K or Na nitrate 25, picrate 10, sulfur 5,
carbon 10 & incombustible salt 10%
Caseless Bomb. Development of such bomb is Re/s: l)Cundill(1889) in Mp 5, 305(1892) 2)
discussed by A. L. Forchielli & J. H. Veltman in Daniel(1902), 117-1$
conf PATR 1855( 1951)
Cast Composite Propellants for Rockets. See
Caseless Cartridge. See Ref 24 under Cartridge under CAST PROPELLANTS
Cases
Cast Double-Base Propellants for Rockets. See
Casemate. A fortified position or chamber under CAST PROPELLANTS
(usually of concrete) in which ammunition can be
stored and cannons or other weapons may be Cast Explosives. Ezpls melting at temps below
placed to fire thru embrasures. AISO, an armored 100° (such as TNT, mp ca 81°) and which are
enclosure “for a cannon or ammo on a warship usually loaded iin ammo by casting (see under
 C 84

Loading of Ammunition). Expl mixts contg at Casting Powder. See under CAST PROPELLANTS
least one of the low-melting components, in
fairly large propn, can also be cast-loaded. In Casting Powder No 1. See Corditite Casting
some countries, expls melting at higher than Powder under CORDITES
100° were allowed to be cast. For example,
PA(mp ca 12 2°) was cast-loaded by the Casting Solvent. See under CAST PROPELLANTS
Japanese in their “Shimose” shells
Following are US military expls which can Casting Techniques for Explosives. See under
be cast-loaded: Amatols(AN 60 or 50 & TNT 40 to Loading of Ammunition
50%), Baratol(Ba nitrate 67 & TNT 33%),
Baronal(Ba nitrate 50, TNT 35 & Al 15%) CAST PROPELLANTS. These proplnts (not to be
Composition B(RDX 60 & TNT 40% with 1% wax confused with Molded Composite Propellants) are
added), Cyclotols(RDX 75,70,65 or 60 & TNT 25, obtained by filling a mold contg granules of a
30,35 or 40%), DBX(AN 21, RDX 21, TNT 40 & proplnt material with a plasticizing liquid, and
Al 18%), Ednatol(EDNA 55 & TNT 45%), heating the resulting mixt until a fairly homogeneous
Pentolit(PETN 50 & TNT 50%), Picratol(Amm mass is obtained
picrate 52 & TNT 48%), Plumbatol(Pb nitrate 70 & By using casting techniques, it is possible
TNT 30%), PTX-1 (RDX 30, Tetryl 50 & TNT 20%1 to obtain grains of any desired shape or size.
PTX-2(RDX 44-41, PETN 26-28 & TNT 28-33%), The work on prepn of cast proplnts for use in
Tetrytols(Tetryl 80,75,70 or 65 & TNT 20, 25, rockets was initiated in the US in 1944
30 or 35%), TNT, Torpex(RDX 42, TNT 40 & Al (Addrd Ref e)
18%); Trimonite(PA 88-90 & MNN 12-10%) and Casting of proplnts techniques may be
Tritonal (TNT 80 & Al 20%) subdivided into: A)Manuf of cast homogeneous
Re/: W.R. Tomlinson, Jr & O. E. Sheffield, proplnts B)Manuf of proplnts by slurry casting and
c‘Properties of Explosives of Military Interest”, C)Manuf of cast composite proplnts
PATR 1740, Rev 1(1958) A) Manuf of Cast Homogeneous Propellants. This
includes, solvent, solventless- or ball-proplnts as
Cast Explosives of Winning. Incorporation of a starting materials. The method consists of the
small quantity of a monobasic fatty acid(mp following operations:
<100° and contg at least 8 carbon atoms, such as a)prepn of Casting powder~ A colloided proplnt
steraic acid) in expls contg TNT & inorganic which incorporates NC and other ingredients is
nitrates, improves their flow props on casting and made into cylinders ca 0.035” i n diam & length
lessens the tendency of the chge to segregate. (using the standard solvent extrusion method) or
Eg: TNT 34, AN 34, Na nitrate 30, chalk 0.9 & made into spheres ca 0.03” in diam (using the
stearic acid 0.1 % process described under BALL POWDER)
Ref: C. H. Winning, USP 2733139(1956) & CA b)Prepn of Casting Solvent. A liquid expl
50, 6796( 1956) plasticizer, such NG, NG + NGc or DEGDN is
mixed with non-expl plasticizer> such as DBuph,
Casthelaz & Désignolle proposed in 1867( BritP DMePh or triacetin and a stabilizer, such as
3469) several expl compns of which the foIlowing EtCentr. The resulting mixt is evacuated to
might be considered as typical: a)K picrate 55 & remove air and volatiles
K chlorate 45% b)K picrate 35, K chlorate 47 & c) Prepn of Mold(Beaker). A mold for solid
K ferrocyanide 18% c)K picrate 37, K chlorate rocket proplnt grains having internal burning
18 & Pb chromate 45 d)pb picrate 43, K chlorate configuration, is prepd from a cellulose acetate or
16 & Pb chromate 41% e) pb picrate 37, K chlorate ethyl cellulose sheet(’ ‘inhibitor”), 1/8 to 1/2”
26, Pb chromate 35 & charcoal 2% thick, by wrapping and cementing it about a
Refs: l)Cundill( 1889) in MP 5, 318(1892) 2) cylindrical mandrel to form a cylinder of required
Daniel(1902), 189 diam. The bottom end of the cylinder is closed
with a plastic disc and the ensemble is placed
Casting, Centrifugal. See Centrifugal Casting inside a heavy-walled container, which has
provisions for attaching the cores(usually made
Casting of Explosives. See under Loading of of Al) which form the perforation of the grain
Ammunition (Ref 2,PP 58-9 & Ref 3,P 249)
c) Filling Operation. With the cores in place, the

—— —. — _—.—.——-—-
 C 85

beaker is filled totwo-thirdsof available space with an av particle size of 250 microns
with “casting powder”. After closing and The slurring methods have the advantage of
sealing the top of beaker, the entire unit is greater simplicity and versatility, and lower cost
evacuated to remove air, residual moisture and than the standard casting process(Ref 3,p 251)
other volatiles trapped among the granules. The SIurrying methods have been used in prepn
interstitial spaces remaining betw the granules of of some cast composite proplnts
casting powder are now filled with casting (See also AddnlRefs g,h,j,l & m)
solvent, also evacuted prior to use. Filling may C)Manu/ of Cast Composite Propellants,
be done from the top of the mold, from the bottom, Composite proplnts, based on inorg salts as
or radially from perforated cores. The rate of oxidizers and organic plastics as fuel- binders,
filling should be fast enough so that the total ckn be manufd as “free-standing” and “case
quantity can be added before the swelling of the -bonded” charges. The free-standing chges can
granules can appreciably interfere with the flow. be made either by extrusion or by casting into a
After the solvent fills all the interstices betw the beaker-similar to the procedure described above
individual grains, the feeding is stopped and the under Manuf of Cast Homogeneous Propellants
beaker is sealed (See also Ref 2,P 60)
d)Curing. In this operation rhe beaker with When the rocket chamber is used as the
contents is heated at 600(1400F) in an oven until mold for casting the proplnt, the charge is called
the solvent penetrates the granules making them “case-bonded”. For this the inner surface of the
coalesce into a single, nearly homogeneous mass. chamber must be cleaned and sprayed with some
Since this is purely a physical phenomenon, there binder material which acts also as an inhibitor.
is practically no shrinkage on curing. When Along with chamber prepn comes the prepn of
using ball proplnts as casting powders, the grains cores or ‘ ‘risers” which provides the mold for the
do not entirely lose their original shape on perforations of the grain. The material used for
curing, because they have a case-hardened casting is obtained by adding a finely ground
outer shell. Such cast proplnts are more fragile oxidizer of required particle size to the ‘(premix”,
than the original grains The c‘premix” is prepd by blending the fuel
After curing, the cast is annealed by a binder with the necessary curing agent, inert
gradual cooling proceduxe and inspected by additives, and ballistic modifiers as described in
x-rays for possible defects(such as voids) and Ref 2,pp 62-4. After adding the oxidizer and
then machined to conform to required dimensions. thoroughly blending it with premix, the resulting
This type of cast proplnt is not “case-bonded” to t ‘slurry “ is poured into the rocket chamber. After
the WSIIS of the rocket motor chamber and does the cores are lowered into the chamber and
not possess the added strength afforded by such secured in place, the chamber is placed in the
bonding (Ref 2,pp 58-60)(See also Ref l,pp 102-4 ‘ ‘curing” oven where the temp is gradually
and Addrd Refs a,b & c)” raised to as high as 300°F(1490C). After
Compns of some “casting powders” and “curing” is complete the cores are removed,
“casting solvents” are given in Addnl Refs d, excess proplnt cur away, and the nozzle
e&f) assemblies attached(Ref 2,pp 64-5)
B)Manzi/ of Propellants by Slurry Casting. In , Following are examples of cast composite
order to increase the versatility of the casting proplnts: a)A eroplex proplnts are prepd by
process a number of methods have been developed mixing Amm or K perchIorate with resin, as a
which avoid the necessity of making “casting binding material and pouring the resulting slurry
powder”. AH the ingredients are simply blended into a mold (See also Vol l,p A108-R) b)
in a mixer, generally under vacuum, and the Plastisol proplnts are made of approx 75% Amm
resulting “slurry” poured into the mold and Perchlorate and 25% of a mixt in equal parts of
“cured” at 60°. The critical feature is the finely divided polyvinyl chloride and non-soluble
form of the NC, the fibrous form being plasticizer. The mixt solidifies when heated
inadmissible because of its high rate of swelling c)P olysulfide proplnts are prepd by suspending
and soln. Various types of colloided NC have granular Amm perchlorate in a polysulfide
been used, including granules of a few microns synthetic rubber mixed with small quantity of
in diam. One variation of slurry cast proplnt ingredients which serve as vulcanizing agents,
developed by Hercules Powder Co, uses a reinforcing agents, and burning-rate accelerators.
partially colloided form of NC, called “densified” The resulting slurry is cast into the rocket
 c 86

motor chamber and cured from 1 to 3 days at J. J.O’Neill, Jr, USP 2916775(1959) &CA 54,
200°F(ca 93°C)(Ref 4,pp 32-3). The 8088( 1960) [Large grains of rocket proplnt are
polysulfide rubber has been used in Thiocol prepd by treatment of NC proplnt spheres ca
proplnts(Ref 2,p 62)(See also Ref 1,pp 101-2 and 0.00 1“ in diam (such as described under BALL
AddnlRef a) POWDER) with at least 25% by voi of dewatered
Refs: l)R.A.Connor, Edit, “Summary Technical deterrents, such as DBu-phthalate or sebacate,
Report of Division 8, NDRC;’ Vol 1, Washington, DiMe-sebacate or phthalate, triacetin, etc. For
DC(1946), 89( Casting techniques); 101-2(Cast double-base proplnts, NG, DEGDN, NGc or
perchlorate proplnts); 102-4(Cast double-base Butanetriol Trinitrate is incorporated. For
proplnrs) 2) F. A, Warren ~%ocket Propellants”, example, 56.18 parts of spheres(consisting of
Renhold, NY( 1958), 58-68 3)R.Steinberger, PP 12.6% N-NC 87.7, DNT 11, EtCentr 1 & C black
249-51 in “The Chemistry of Propellants”, A O. 3%) were held at 10mm in a {‘sigma-blade mixer”
Meeting Organized by the AGARD Combustion and for 16hrs. Then 37 parts of similarly treated liq
Propulsion Panel, Paris, France in June 1959, mixt(consisting of NG 74, DMePh 25 & EtCentr
Pergamon Press, NY( 1960), 249-51 4)B .Kit & 1%) was added with agitation. Agitation was
D.S.Evered, “Rocket Propellants HandbookJ’ continued until even distribution of spheres in
Macmillan, NY(1960), 32-3 liquid was achieved, After pouring the slurry
A ddnl Re/s: a)OSRD Report 5580( 1945) (Techniques into a mold, it was heated at 75° until the spheres
of prepn of cast double-base proplnts) a, )OSRD were substantially dissolved. When cool, the
Rept 5582( 1945 )(Cast perchlorate proplnts uniform grain was removed from the mold] m)
based on thermoserting high polymers) b)OSRD D.W.Ryker, USP 2917379(1959) & CA 54, 8088
Rept 5593( 1945)( Experimental study of factors ( 1960)(Same as above, but the hot mixt is not
affecting the stability and consolidation of cast poured into molds but into a worm- or screw-feed
proplnts) c)OSRD Rept 5759( 1945)(StudJes app, such as “Moyno” pump, heated to 75-80° so
relating to the development of cast proplnts with that complete soln of spheres is attained. Then
special reference to the mechanism of consoli- the mixt is extruded and cut into grains of
dation) d)OSRD Rept 6298(1945) [Cast double desired length) n)A.Andrew, USP 2929107(1960)&
-base jet proplnt prepd by adding to the grains of CA 54, l1561(1960)(Prepn of globules 0.002
{ ‘casting powder”, consisting of NC(12.6% N) 89, -0.004” in diam of colloided NC suitable as
DNT 10 & stabilizer 1%, placed in a mold the primary materials in plastics or in cast proplnts)
“‘casting liquid” consisting of a mixt of NG & o)A.W.Sloan & D. J. Mann, USP 2931800(1960) & CA
triacetin] e)OSRD Rept 5577(1946) [A general 54, 14722( 1960)( Prepn of small, dense particles
survey of the development of cast double-base of NC suitable as primary materials in lacquers
proplnts by NDRC as of Nov 1945. The reco- or cast proplnts) p) V. Grassie, USP 2946673(1960)
mmended proplnt was prepd from the “casting & CA 54, 21764( 1960)( Prepn of a cast double-base
powder” consisting of NC( 13.15% N) 74, NG 20, proplnt by combining in a mold granular NC
DEtPh 5 & EtCentr 1% with carbon black, added having a bulk d of at least 25 lb/cu ft with a
0.5% to which was added the “casting solvent” casting liquid consisting of NG and desensitizing
consisting of NG 65, DMePh 34 & EtCentr 1%] plasticizers. The granular NC is produced by
f)S.Wachtell, PATR 1731 (1949 )(Chromatographic agitating fibrous NC in an aq bath contg an org
-spectrographic method for detg DEtPh in Type 1 liq which destroys the fibrous structure of the NC
casring proplnt) g)C.Ribaudo, PATR 2014(1954) without dissoln) r)Anon, “Cast Double-Base
(C) h)S.M.Kaye, PATR 2015(1954)(C) i) Propellants”, pp 186-95 in Vol 2 of “complete
A. H. Castelli et al, PATR 2021( 1954)( U)(Simple, Draft Manuscript ORDP 20-176, Explosives Series,
rapid IR analysis of ~~casting solvent”, such as Solid Propellants”, Hercules Powder Co,
one contg NG 70, triacetin 29 & 2-nitro-DPhA 1%) Wilmington, Del( 1960)( Conf)(Not used as a source
j)C.Ribaudo, PATR 2071(1954)(C) k) of info) s)Allegany Ballistics Laboratory,
J .Reinhart et al of NOL, “Nitrasol Propellants “Status of Research and Engineering Projects”,
-Composite Propellant Formulations Based on a ABL/QPR-35, Contract NOrd 16640(Dec 1, 1961
P lastisol-Nitrocellulos e-PentaeryttiitoI -Feb 28, 1962)( Conf)(Not used as a source of info)
Trinitrate Binder’ ‘(U), Bull of the 14th Meeting of t)Imperial Chemical Industries Ltd, “Research
the Joint Army-Navy-Air Force Solid Propellat and Development Work on Cast Double-Base
Group, Johns Hopkins University, Silver Spring, Propellant Rockets”, (Feb 1962)( Conf)(Not used
Md(1958)(Conf)(Not used as a source of info) 1) as a source of info)
 C 87

Castor oil (Ricinus Oil). A pale yel to colorless, castor oil lYop 226) b) White star with parachute:
very viscous oil, consisting tnostly(ca 80%) of Ba nitrate 70.5, Al powder 19, AI grains 9.5 &
ricinolein (triglyceride of ricinoleic acid), castor oil 1.0% (p 227) c)Green star with
C3H5(C18H3303)3; fr p ca - 10°,d 0.957 to 0.967’ at parachute: Ba chlorate 90, shellac 8 & castor oil
15.5/15.5°, n~ 1.476-1.478 at 25°, viscosity 6-8 2% (p 227) and d)White pyrotechnic light:Ba nitrate
poises at 25°, saponification value 178 and 74, K nitrate 6, Al powder 22, gum arabic 4 and
iodine value 85; sol in ale, eth, benz, chlf & CS2. castor oil 6z(p 239)
Three commercial grades are available in the US: Kirk & Othmer(Ref 7,p 323) lists the
USP XIII, No 1 & No 3. Castor oil is derived from following illuminating flare compns employing
the seeds of the plant Ricinus communis by cold castor oil: a)Ba nitrate 36, Mg(coated with 6% of
-pressing for the first grade of medicinal oil and linseed oil) 42, Al 8, Na oxalate 12, linseed oil 1
by hot-pressing for technical grades. The USP & castor oil 1% and b)Ba nitrate 68, Al 21, Na
grade oil is used in medicines(as purgative) and in oxalate 5, sulfur 4 & castor oil 2%
cosmetics, while tech grades are used as high Castor Oil, Dehydrated Heating of castor oil to
-grade lubricants (especially for internal 200-240° in the presence of catalysts, such as
combustion engines, )(such as in airplanes), as Sn or Ti oxides yields a partially dehydrated oil
hydraulic fluid in brakes, as recoil fluid for guns, which is miscible with mineral oils. It was used
as softener in NC lacquers & in artificial leather during WWI under the name of ‘RCastorlubrin” for
finishes, in manuf of transparent soaps, and in Lubrication of aircraft engines, but was replaced
resins & plastics(Refs 2,5 & 9)(See also Ref 10 Iater by high grade mineral Lubricating oiIs. It is
and AddnlRefs f,g,h & i) still widely used in brake fluids, shock
Castor oil has aIso been used in some expl absorbers, and shimmy damper systems. k is also
and pyrotechnic compns mostly as a coating agent frequently used in combination with light mineral
to reduce the hygroscopicity and sensitivity(to oils, glycols, etc.
shock and friction) of some ingredients Heating of castor oil to 250-300° in the
Below are examples of French Cheddites presence of catalysts(direct method) or by
(Street Explosives) using castor oil: employing one of the indirect methods, such as
Accdg to Weingarten(Ref 12), castor oil has described in Ref s,p 243, produces completely
been used in some US pyrotechnic compns, but dehydrated oil. This oil possesses good drying
there is a tendency to repIace it, as well as other props and is widely used as a substitute for tung
natural oiIs, with synthetic materials. Following oil. The term “dehydrated castor oil” is used to
are exaniples of US compns using castor oil: a) denote this type of oil (Ref 5,pp 241-3 )(See ako
Sr nitrate 50, Mg 30, Ti oxide 10, polyvinyl Ref 11)
chloride 6, castor oil 2 & linseed oil 2% b)Ba Castor Oil, Hydrogenated. Since ricinoleic acid is
nitrate 76, Al flakes 6, Al atomized 12, sulfur 4 & an unsaturated acid, hydrogen can be added to its
castor oil 2% double-bond, yieldirig a satd acid of higher mp
Izzo(Ref 6) lists the foIlowing pyro compns with max ca 87°. Hydrogenation may be conducted
using castor oil: a) White star for French by introducing hydrogen under pressure into the
military signal cartridge used in Vdry pistol: Ba thoroughly agitated oil at temps of the order of
nitrate 57, Al powd 30, Sb sulfide 6, cryolite 6 & 150° and in the presence of a Ni catalyst. It can

K chlorate 70.0 75.0 74.6 80.0 80.0 79.0 -- -

Na chlorate - -_ _ -- - 79.0 - -
Amm perchlorate - —_ _ -—— 82.0 50.0 “
Na nitrate 80.0 - - -- - .- 30.0
P icrino- 10.0 20.() - -— - -- —
napthalene
DNB 11.6 ___ —- -
MNN -_ 5.5 12.0 13.0 1.0 -- —
DNT —_ _ 2.0 15.0 16. o 13.0 15.0
Starch 9.2 -_ 14.9 --- ---
Castor oil 9.2 10.0 5+0 5.0 8.0 5.0 5.0 5.0 5.0 5.0
Refs 1 144 444 444
 c 88

be used as a substitute for waxes(Ref 3,pp 243-4) Production Mgr 23, 3-4, 6 & 8-10(1943) & CA 37,
Castor Oil, Nitrated. Brighton(AddnlRef a) prepd, 3961 (1943 )(Castor oil in war and industry) g)
by treating castor oil with dil nitric acid, a A. Kraus, Farbe u Lack 57, 433-7(1951) & CA
reddish-brn viscid oil with Ncontent betw 2.3 & 46, 1777-8(1952) [Uses of raw castor oil and of
3.8% and d ca 1.05. The substance was sol in oxidized castor oil(known as C‘blown castor oil$’
acet, eth & AcOH, but insol in CS2. It did not or Limorol) in NC lacquer films] h)A.Kraus,
decomp at 100° but slowly darkened. Radcliffe & Ibid 60, 185-6(1954) & CA 48, 12422(1954)
Polychronis(Addnl Ref b)nitrated castor oil and (Lacquers made of NC & castor o~l were only
ricinoleic acid (as well as some other fatty acids) slightly yellowed when exposed to sunlight, but
with coned or 99% fuming nitric acid and obtained they did not pass the t ‘fold” test) i)K.Murai et a~
products of low N content. Keck(Addnl Ref c) JOilChemistq’Sot, Japan 3, 2-6(1954)&CA 50,
patented a proplnt consisting of NC and nitrated 2 50( 1956)(Study of plasticizers for polyvinyl
castor oil chloride obtained from castor-oil fatty acid, and
Castor Oil, Oxidized, Heating of castor oils in lower fatty acids of coconut oil)
intimate contact with air or oxygen at temps of 80
to 130°, with or wo a catalyst, produce oils of Castor oil, Analytical. See “ASTM Standards”
high viscosity and higher d, than untreated castor ( 1955), Part 4, 0555-54, pp 234-56 (Tests of
oils. The oxidized oils, known also as ‘tblown drying oils, such as castor oil); D960-52, 367-8
oils” are used as plasticizers in lacquers, (Std specs and tests for raw castor oil);
artificial leathers, oil cloths and similar products 0961 -55T, 224-5 (Tentative specs and tests for
(Ref 5,p 241). It was claimed by Nakamura dehydrated castor oil)
(AddnlRef d) that a small quantity of peroxide
was formed when castor oil was treated with air Castro Powder. An Amer expl proposed in 1884;
at ca 155°. Mondain-Monval & Marteau(Addnl K chlorate 50.00, bran 43.75 & Sb sulfide 6.75%
Ref e) claimed that direct oxidation of castor oil Re/s: l)Daniel(1902), 118 2)P~rez Ara(1945), 213
(as well as of some other vegetable oils) by air
in a heated glass tube also produced peroxides Catactines. Expls patented in 1s88 by Chandelon
Refs: l)Daniel(1902), 472 2)Thorpe 2(1938), for use in grains or compressed. They consisted
420-22 3)CondChemDict( 1942), 288(Cheddites) of mixts of one of the organic picrates or
4)Davis( 1943), 258, 269, 358-60 & 365 5)Kirk & chloropicrates with sulfur, carbon and an oxygen
0thm6r 3(1949), 237-44 6)1220, Pirotecnia( 1950), carrier, such as a nitrate or chlorate of alkaline
226-7 & 239 7)Kirk & Othmer 11(1953), 323 8) or alkaline-earth metals
Sax( 1957), 444( Toxicity & fire hazard of castor Refs: l)CundiH(1889) in MP 5, 306(1892) 2)
oil) 9)CondChemDict(196 1), 229 10)US Daniel(1902), 118
Specification J J J-C-86 (Castor oil, technical) 11)
US Military Specifications MIL-C-15179A(Castor Catalysis. It may be defined as the effect
oil, dehydrated) 12)G.Weingarten, PicArsn, produced on the rate of reaction either by a small
Dover, NJ ;private communication(19k2) quantity of a substance(called c‘catalyst”),
Addnl Re/.s: a)R.Brighton, JSCI 36, 984-6(1917) & which appeares to be unchanged in the reaction
CA 12, 98(1918 )( Nitration of castor oil with dil products, or by some physical energy, such as
nitric acid) b)L.G.Radcliffe & C. Polychronis, radiation, electricity or magnetism. Reactions
JSocDyers Colorants 36, 65-76(1920) &CA 14, accelerated by catalysts are called “positive
3330( 1920)( Nitration of castor oil and of catalytic reactions “ ~ while those retarded are
ricinoleic acid with coned and 99% fuming known as ~!negative catalytic reactions”. The
nitric acid) c)C.H.Keck, USP 165 1459(1927) & Phenomenon of cataly;is is essentially a branch
CA 22, 870(1928)(A proplnt consisting of NC and of e‘surface chemistry”
nitrated castor oil) d)M.Nakamurag JSocChemInd Historical, Accdg to Kirk & Othmer(Ref 12,p 245),
Japan 40, 229(1937) & CA 31, 7681(1937) the fact that a them reaction can be aided by
(Formation of small quantity of peroxide on the addn of certain substances was known to
treating castor oil with air at ca 155°) e) the alchemists in the Middle Ages and by the end
P .Mondain-Monval & S, Marteau, AnnCombustibles of 18th and beginning of 19th century several
Liquides 12, 923-8(1937) & CA 32, 3154(1938) industrial processes were known such as
(Formation of peroxide by heating castor oil with hydrolysis of starch by acids(ParmentierY 1781)
air in a glass tube) f)J .E .Good, Paint Varnish and the lead-chamber sulfuric acid manuf

. . .. .
 C 89

(Clement & Desormes, 1806). Berzelius described NY(1946) 10)R.H.Griffith, “The Mechanism of
and classified in 1s36 the known reactions in Contact Catalysis”, OxfordUnivPress, London
which the rate was altered by the presence of (1946) 1 l)W.G.Frankenburg, VJ.Komarewsky &
certain substances, under the name of E .K,Rideal, Edits, “Advances in Catalysis and
“catalysis” Related Subjects”, Academic Press”, NY, Vols
The most important work on catalysis was 1-10( 1948-1958) 12)Kirk & othmer 3(1949),
done, however, in the present century, first in 245-72 (Catalysis) 13)S.G.Gregg, “The Surface
France by Sabatier(in collaboration with Chemistry of Solids”, Reinhold, NY(1951),
Sanderens) and in Russia by Ipatieff(in collabn with 245-70 (Catalysis and chemisorption) 14)P .H.
Zelinsky & others). In Germany the work was Emmett, Edit, “Catalysis”, Reinhold, NY Vols
done by Haber & the IG Farbenindustrie group; 1-7( 1954-1960) 15)E.Mo11oY & E. Carr,
in England by Hinshelwood & Rideal; and in US “Catalysts”, Newness, London(1955) 16)v.I.
by Langmuir & Taylor Komarewsky et al, Edits in Vol 2 of Weiss berger’s
At present catalytlc processes are used on a ‘ ‘Technique of organic Chemistry”, Interscience,
very large scale for the prepn of both lnorg and NY(1956) 17)Kirk & Othmer, FirstSuppl(1957),
organic compds 144-50(Catalysis) 18)C.H.Collier, Edit,
Following are examples of catalytic “Catalysis in Practice”, Reinhold, NY(1957)
processes which are of interest for those working 19) A. V. Topchiev, “Boron Fluoride and Its
in explosives or ammunition plants: a)Combination Compounds as Catalysts in Organic Chemistry”,
of hydrogen and nitrogen to form ammonia in Translated from the Russian by J.J .Greaves,
presence of ferric oxide catalyst at 400 to 600° Pergamon Press, NY(1959) 20) J. E. Germain,
and 200 to 1000 atm pressure b) Oxidation of “Catalvse H~t~rogane”, Dunod,, Pais(1959)
ammonia to nitrogen oxides in presence of Pt Addn/ Re/.s: a)W.Briin, USP 211 1203(1$138) & CA
gauze as catalyst c) Oxidation of sulfur dioxide 32, 3617(1938) [Incorporation in a priming mixt
to trioxide in presence of vanadium pentoxide at (such as contg Pb thiocyanate, Ba nitrate and
500° d)catalytic prepn of benzene and toluene LST) about 2%, or less of a catalyst, is claimed
from petroleum. Nitration of benzene and toluene to accelerate the reaction and to lower the temp.
yields high expls, such as TNB and TNT These catalysts included metals or alloys(such
Refs: See under Catalyst as Ag, Bi$ Cu, Fe or Pt)$ oxides(such as
Mn02, Coo) or a salt of metallo-acid(such as Na
Catalyst or Catalyzer, It is a substance which tungstate)] b)Katalyst-Chemie AG, FrP 821767
affects the speed of a reaction, (or even starts (1937) & SwissP 192363(1937); CA 32, 3964&
it), but remains chemically unchanged at the end. 4173( 1938)( Use of catalysts, such as Cr, W,
It is known, however, that catalysts may take Mo-Ta-Ni, V, Ga or In in nitration of
part in some reactions and may be physically naphthalene, glycerin & other org compds) c)G, F.
changed. For more inf~ on catalysts! see Refs Hennion, USP 2314212(1943) & CA 37, 5077
Refs: l)P .Sabatier, ‘{La Catalyse en Chimie ( 1943XUse of BF3 as catalyst in nitration of
Organique”, English Translation, Wiley, NY cyclic org compds) d)M.Senkus, USP 23332491
(1923) 2)W.Langenbeck, ‘tDie Organischen (1944) & CA 38, 1749( 1944)(Use of reducing
Katalysatoren”, Springer, Berlin(1935) agents such as S, C,acetone or 2-nitroheptane as
(Lithoprinted by Edwards Bros, AnnArbor, Mich) catalysts in Iiq-phase nitrations of satd
3)V.N.Ipatieff, “Catalytic Reactions at High aliphatic hydrocarbons) e)N.A.Valyashko et al,
Pressures and Temperatures”, Macmillan, NY TrudyKhar’kovKhim-TekhnolInst No 4, 48-59
(1937) 4)Thorpe 2(1938), 422-9(Catalysis in (1944) & CA 42, 1218(1948)(Nitration of toluene
industrial chemistry) 5)S.Berkman, J .C. with N02 without H2S04, but in presence of
Morrell & G, Egloff, “Catalysis, Inorganic and catalysts) f)N.Levy, USP 2394315(1946) & CA
Organic”, Reinhold, NY(1940) 6) G. M. Schwab, 40, 2454( 1946)( Use of silicate catalysts contg
{ ‘Handbuch der Katalyse”, VOIS 1-7, Springer, Ag or Sb or both in prepn of nitroparaffins) g)C.V.
Wien(1940-1943)( Lithoprinted by Edwards Bros, Caesar & M.Goldfrank, JACS 68, 372-5(1946) &
AnnArbor, Mich) 7)Davis(1943), 276-7 & 377 8) CA 40, 3633( 1946)@se of NaF as catalyst in
H. W. Lohse, “Catalytic Chemistry”, ChemPubgCo, nitration of starches with N20~ ) h)B.Hass &
NY(1945) 9)H.E.Emmett, “Catalysis and Its H.Stecher, IEC 39, 817-21(1947) & CA 41, 5436
Industrial Applications”, pp 214-42 in vol 6 of ( 1947)(Use of catalysts in vapor-phase nitrations
J .Alexander’s, “Colloid Chemistry”, Reinhold, of satd hydrocarbons) i) A. E. Rout, BritP 586732
 c 90

(1937) & USP 2431585(1947); CA 41, 6897(1947) & various salts on combustion of proplnts, Pascal
42, 1605( 1948)( Use of catalysts in vapor-phase et al conducted a series of experiments
nitrations of aromatic hydrocarbons) j )R.M. commencing with combstn of carbon in atm of
Schramm & F .H.Westheimer, JACS 70, 1782-4 nitric oxide. As catalysts! the salts of K, Na,
( 1948)( Use of catalysts in nitration of anisole) Cs, Rb, Sr & Cu were tried. The best results
k)W.J.Chute et al, CanJRes 26B, 89-103 & were obtained with K bitartrate and then
114-37(1948); CA 42, 4918 & 4919( 1948)( Catalyzed followed Na dinitronaphtholsulfonate(Yellow 0S),
nitration of amines) l)A.I.Titov & A.N. K chloride, Na carbonate & Sr chloride] x)J.
Baryshnikov, ZhObshchKhim 17, 829-35(1947)& Cason et al, USP 2686804(1954) & CA 49, 2075
CA 42, 3340( 1948)(Mechanism of nitration of (1955 )(Use of Br or Br compds as catalysts in
aromatic compds in the presence of mercury nitrating secondary amines or their nitrates with
salts) m)T.Connor, CanJRes 26B, 294-308(1948) mixts of 98% nitric acid and acetic anhydride) y)
& CA 42, 5844( 1948)( Use of catalysts in nitration J .A.Hannum, USP 2692194& 2692195(1954); CA
of secondary aliphatic amines) n)N. Levy et al, 49, 2736-8(1955) { Addn of small amts of
USP 2455425(1948) & CA 43, 2220( 1949)( Nitration substances, such as the pyridine salt of
of paraffins with N02 in presence of catalysts) uranylacetylacetonate, [U02(C5H702)3H. C5H5NI,
o)K.W.Gee, USP 2464572(1949) & CA 43, 4285 or of the alkylamine chromates or dichromates to
( 1949)( Use of catalysts in prepn of nitroparaffins) Iiq nitroaliphatic fuels catalyzes the combustion
p) A. I. Titov & N .G.Laptev, ZhObshchKhim 19, reaction by promoting smooth burning without
229-39 & 267-78(1949); CA 44, 5828(1950) & 43, lowering expln temp of the fuel} z)A.I.Titov &
6585( 1949)( Mechanism of catalytic nitration of A.N.Baryshnikova, ZhObshchKhim 24, 2005-8 &
aromatic compds in the presence of Hg salts) 2040-4(1954); CA 50, 10667(1956) & 49, 14659
g)G.S.Samuelson et al, JACS 72, 3872-4(1950) & ( 1955)(Mechanism of catalytic nitrations of
CA 45, 2885( 1951)( Hydrogenation of nitrocompds aromatic compds) aa)S.Z.Roginskii, ReferatZh-
with Raney Ni treated with chioroplatinic acid Khim 1956, Abstt No 53971 & CA 53, 3857(1959)
and with alkali) p)J .A.Grand & R. Miller, USP (Mechanism of catalysis on the basis of isotope
2555333(1951) & CA 45, 7337( 1951)( Use of Cu data) bb)M.A.Cook & F. A. Olson, C & EN 34,
chromite as combustion catalyst in solid 4434-6( 1956) & CA 50, 17453( 1956) (Catalyzed
compressed fuel, such as mixt of NGu 75 & GuN explns occurred with hydrogen-oxygen
25%) r)Anon, ChemEngrg 1951, June, p 183 stoichiometric mixts and also with hydrogen
(Catalytic process for waste disposal developed -oxygen-argon mixts when 14-15 mole % of argon
by D. V. Moses and put into operation at DuPont’s had been incorporated in a steel mixing tank) cc)
Belle Plant, West Virginia, consists of vapor G. R. Thomas, USP 2877263(1959) & CA 53,
-phase catalytic destruction of organic wastes by 14010 (1959)( Use of catalysts in nitration of an
oxidation to C02 & H20. It was claimed that the ester of N-monoalkyl-substitut ed carbamic acid)
method is more convenient than bio-oxidation dd)K.0k06, BiulWojskowejAkadTech in
and less expensive than non-catalytic ,oxidation at JaroslawaDobrowskiego 8, No 1 PraceChem
high temp) s)E.L.BlackaH et al, JCS 1952, 116-20(1959) & CA 54, 19547( 1960)( Use of
28-32 & CA 46, 9392( 1952)( Use of HN02 as picric acid as catalyst in nitration of benzene,
catalyst in nitration of aromatic compds) t) toluene, naphthalene and chlorobenzene)
Krupp Treibstoffwerk GmbI-i, GerP 831393(1952)
& CA 52, 10144( 1958)( Nitration of satd nonaromatic Catalyst(Rocketry). A liq or solid substance
hydrocarbons with N02 in presence of catalytic which, by its contact with a “monoreactant”
amts of free radicals, such as PbEt4, azomethane, fluid, increases the breakdown or reaction rate,
azobenzene or triethylmethyl) u)G.B .B achman & without itself becoming altered in nature or
J .V.Hewett, USP 2597698(1952)&CA 47, 2766 amount. One of the earliest known rocket
( 1953)( Use of small amts of free halogens as applications of a catalyst was in a Ger ATO
catalysts in vapor-phase nitration of aliphatic engine, The “Walter 109-500”. Liquid Ca
hydrocarbons) v)C.C.Price & C.A.Sears, JACS permanganate was sprayed in the thrust chamber
75, 3276-7(1953) & CA 49, 6153( 1955)( Nitration of the motor to make contact with the primary
of aromatic compds with nitryl chloride, CIN02, spray of coned H20Z. The catalyst caused the
in presence of catalysts, such as HF, AIcla or nearly instantaneous breakdown of this mono
BF9) w)P.Pascal et al, MP 35, 335-47(1953) -proplnt into hot steam and oxygen. Other
[In order to det the influence of presence of catalysts considered or tried include: Na

— 1
—..
 c 91

permanganate, Kpermanganate, Mn dioxide& Catechol. See Pyrocatechol

Fe oxide
Re/s: l) A. J. Zaehringer, “SolidPropellant Catergol, A Ger code name for a rocket propellant
Rockets”, AmRocketCo, Wyandotte, Mich(1955), system using catalyst for decomposition
50-1 2) Rocket Encycl(1959), 71 Re/: A.J .Zaehringer, “Solid Propellant Rockets”,
AmerRocketCo, Wyandotte, Mich(1955), 149
Catalytic Ignition(Rocketry). A method of
igniting the main proplnts in a rocket combustion Cathode Ray, Cathode Ray Tube and Cathode
chamber by utilizing a solid or a liq catalyst to Ray (Oscillograph. Cathode ray is an emission
initiate them decompn or breakdown of one of from the cathode(negative electrode) of a
the proplnts and thereby to generate ignition discharge tube, consisting of negatively charged
temp and pressure particIes(eIectrons). The ray is projected at
Ref: Rocket Encycl(1959), 73 right angle to the surface of the cathode. The
discharge of the tube may be caused either by
Catapult(Ancient). One of the “engines of war” alternating high-potential current or by a series
used in ancient times for projecting long darts, of spark discharges. The electrons emitted by
stones and javelins. There were different kinds the cathode travel in straight lines unless
and sizes of catapults to which various names deflected by the action of a magnetic or electric
were given. The smaIIer kinds were in the form field. They differ from beta-rays only in having
of Arbalest(Cros show), which is briefly described lower velocities
in VO1 1 ~p A477 of this Encyclopedia. The Cathode rays have many applications, such
larger catapult consisted of a powerful wood, as in the cathode-ray tube and the cathode-ray
horn or steel bow fastened transversely to a oscillograpb. The former is a vacuum tube in
stand and wound up by means of a windlass which the deflection of an electron beam
fastened upon another stand. One of the varieties indicates on a fluorescent screen instantaneous
couId discharge a whole flight of darts values of the actuating vokages or currents. The
simultaneously and might be considered as the oscillograph incorporates a cathode ray tube and
earliest machine gun. The catapult was smaller is used extensively in ballistics, such as for
and less powerful than the Ballista(qv) and photographing rapid events(See under Cameras,
discharged projectiles at low angle of elevation. High-Speed, Photographic)
Some authorities consider the catapult as one of R e/s: l)C.Cranz, “Lehrbuch der Ballistik”,
the Mangonels(qv)(See also Trebuchet) Erg~nzungsband( 1936), 163 2)J .T.MacGregor
Re/s: l)Greener(1881),p 7 & Fig 4,P 8 2) -Morris, “Cathode Ray Oscillography”, Chapman &
Farrow’s hiilitEncycl 1 (1895), 309-10 3)W. L. Hall, London(1936) 3)G.Parr, “The Low Voltage
Rogers, ArOrdn 15, 339, Fig 5(1935) 4) Cathode Ray Tube and Its Applications”,
EncyclBritannica 5(1952), 23 & 8(1952), 453 5) Chapman & Hall, London(1937) 4)M.Bly, “A
Merriam-Webster’ S( 1961), 351 Guide to Cathode Ray Patterns”, Wiley, NY
(1943) 5) J. F. Rider & S. D. UsIan, “Encyclopedia
Catapult(Modern). Any mechanical device on Cathode-Ray Oscilloscopes and Their Uses”,
utiIizing the recoil of a spring for hurling Rider Publisher, Irrc, NY(1950) 6)EncyclBritannia
grenades or bombs. Also a device for launching 5(1952), 41 6) J. F, Rider, “Obtaining and
an airplane at flying speed? as from an aircraft Interpreting Test Scope Traces”, .Rider Publisher,
carrier. It is usually a carriage accelerated on a Inc, NY(1954) 7)J .H.Ruiter, “Modern
track by deflagration of a proplnt chge or by Oscilloscopes and Their Uses”, Reinhart, NY
hydraulic or steam pressure. This term is also ( 1955) 8)A.Haas, “Oscilloscope Techniques”,
applied to a device moving a rocket or guided Gernsback Library, NY(1958) 9)V.N.Laut & A.L.
missile into the air from a ramp or track and for Lyubovich, “The Cathode Ray Tube Memory of
ejecting a person from an aircraft(See also under the High Speed Electronic Computer of the USSR
Cartridge Activated Devices) Academy of Sciences”, Translated from the Rus
Re/s: l)Glossary of Ord( 1959), 62 2)Merriam by R. Feinstein, Pergamon Press, NY(1960)
-Webster’s( 1961), 351
Cauvet & Baron Explosives. Two formulations
Catapult Take-off. See Assisted Take-off(ATO) were submitted in 1882 to the Commission
in Vol 1,p A497-R of this Encyclopedia Fran$aise des Substances Explosives: a)K
 C 92

chlorate 50 & K ferrocyanide 50% and b)K Cavity Type Transducer suitable for making
chlorate 50, K ferrocyanide 25 & sugar 25% dynamic pressure measurements of ordnance
(Compare with Augendre Powder, Vol l,p A507 of items was discussed by C. L. Pataky, PATR
this Encyclopedia) 2321(1956)(U)
F!e/: Cundill(1888) in Mp 5, 291 & 306(1892)
CBRW. Abbr for Chemical, Biological, and
Cavalii, Giovanni(1808-1879). Ital artillery Radiological Warfare
officer, who introduced many improvements in
weapons and ammunition and made Ital artillery CBS. A plastic HE consisting of RDX 84 &
one of the best of the world butyl srearate 16% with ca 1,5% stabilizer added
Re/: E. Bravetta, SS 3, 241-3(1908) R e/s: l) Anon, “Care, Handling, Preservation
and Destruction of Ammunition”, TM 9-1903(1956),
Cavasenza FigIi, Plant at Casale(Isola). One 77(listed WO giving its compn) Z)Anon, ‘ ‘Ord-
of the Ital exp[ plants nance Safety Manual”, ORDM 7-224, C7 to 1 lW 1-2,
Table 1905, Group 1, item 3 3)E.P.Vail, picArsn;
Cavitated Charge or Hollow Charge. See private communication ( 1962)
Shaped Charge
CBS-128K and CBS-162A, Composit rocket proplnts
Cavitation in Explosive or Propellant Charges.
developed by Grand Central Rocket Co. Their compns
The formation of one or more cavities(air spaces
and props are given in conf “Propellant Manual”,
or voids) in cast-loaded solid, expl or proplnt SPIA M2(1959), Unit No’s 567 & 561
chges is called cavitation (See under Loading of
Ammunition). A cavity in a HE chge of a shell CC. Abbr for Chemical Corps
may cause premature expln in the gun because
of collapse of the chge under the force of CC(Cyclonire-Cannon)p repel I ants. Exptl
acceleration. A cavity in a proplnt chge may double-base proplnts, contg RDX in lieu of NG,
affect its ballistic characteristics( Ref 1). were developed during WWII by rhe DuPont Co.
Cavities in loaded ammo may be discovered by Two compns are as follows: a)CCl: NC(12. 6% N)
x-ray devices such as Betatrons 37.5, RDX 50.0, butylstearate 12.0 & DPhA 0.5
The phenomenon of cavitation occurs also and b)CC2: NC(12.6Z N) 36.5, RDX 53.0,
in liq rocket proplnts where the suction pressure burylstearate 10.0 & DPhA 0.5%. About 0.4% of
is greater than the vapor pressure of the proplntj K nitrate could be added as flash-reducer. The
and bubbles of gas form(Ref 2) proplnt CC2 was intended for use in high-velocity
(See also under Loading of Ammunitition) weapons, such as 90mm AT and T guns. The CC
R efs: I )Glossary of Ord( 1959), 62 2)Rocket proplnts exhibited superior thermochemical props,
Encycl(1959), 73 showed good velocity relationship and better
thermal srability than proplnts contg NG. Their
Cavité au Bloc de Trauzl ou Épreuve au Bloc disadvantage was poor uniformity from round to
de Plomb. French for Trauzl Block Test, also round. The manuf and analytical procedures are
called Lead Block Expansion Test, but con- described in Ref 2( See also CR Propellants)
ducted somewhat differently from the procedure Refs: l)L.Pauling et al, OSRD Rept 5495(1945)
used in US or Germany. A brief description of Fr 2) E. I.DuPont de Nemours & Co, OSRD 6216
method, also called “Coefficient d’utilisation ( 1945) 3)Anon, ‘ ‘Summary Technical Report of
Pratique”, is given in Vol 1, p IX of this Ency- Division 8, NDRC”, Vol 1, Washington, DC(1946)
clopedia
CD. A Brit “solvent” colloidal proplnt for
Cavity. See under Cavitation small arms ammo. Its compn & props are given
in conf “Propellant Manual”, SPIA MX1959)~
Cavity Charge. See Shaped Charge Unit No 366

Cavity Effect. Same as Munroe-Neumann CDT(80). A cast, rocket, double-base proplnt

Effect, Shaped Charge Effect or Hollow Charge developed at ABL. Its compn & props are
Effect given in conf “Propellant Manual”, SPIA M2
( 1959), Unit NO 578
 c 93

CE(Composition Exploding). Brit designation velocity 2980m/sec. Its OB to C02 was

of Tetryl( 2,4,6 -Trinitrophenylmethy lnitramine) positive
Re{: L.M~dard, MAF 22, 596-7(1948)
Ceipek’s Explosives. Blasting expls developed
befpre WWI in Austria: a)AN 88, carbonized Cellite. A plastic compd used in films, etc prepd
tumeric pdr 6.2s & wood charcoal 5.75% b)AN 88, by mixing an alcoholic soln of the lower
carbonized pdr of curcuma root 1.05, carbonized acetylated products of cellulose(cellulose
pdr of sandal wood 0.9S & nitrated pdr of acetate) with camphor, followed by drying.
curcuma root 10% c)AN 78-87, TNT 4-13.5, Cellite films are less flammable than celluloid
carbonized turmeric pdr 5.5-10$ carbonized films(Ref 2)
cereal flour O-3 & NaCl O-3% d)AN 80-90 & The term Cellite has also been applied
nitrated turmeric pdr 20-10% to the aq soln of Na sulfite used for the
Re/s: I)N.Ceipek, USP 988244(1911) & CA 5, purification of crude TNT(Ref 1)
1995(1911) 2)N.Ceipek, Britp’s 9742 & 9743 R e/s: l)clift & Fedoroff, 1(1942), Chap V1,P 3
(1911) & CA 5, 3342(1911) 3)N.Ceipek, USP 2)Gardner’s Chem Synonyms(1948), 121 3)
1033537(1912) & CA 6, 2687(1912 CondChemDict(196 1)-not found

“Celite”. Trademark for diatomaceous earth Cellobiose and Derivatives

and a line of produc ts processed from it by CeUobiose(formerly called Cellose),
Johns-Manville. Celites occur at Lompoc, CHO, ~ 22 , , ; mw 342.30. It seems that ~-isomer
Calif as white to pale-brownish, porous materials was never isolated. The ~-cellobiose, col
varying in d from 0.24 to O. 34g/cc. They are microscopic crysts(from dil ale), contains from
capable of absorbing 300 to 400% of water by wt. 0.25 go 0.5 mole H20; mp ca 225° with decompn,
A typical analysis of celite, on ignited basis, is: [rzl~o +34.8°(in 6% aq soln). Can be prepd by
Si02 92.7, A1203 3.8, Fe203 1.4, CaCWMgO 1.0 treating dry a-cellulose octaiicetate with absol
and potash & soda 0.9z; unaccounted materials methanol in which some Na is dissolved(Ref 2).
O. 2%. Celites are used as filter aids, as filIers It can also be prepd by saponification of
in plastics$ as chromatographic adsorption ~-cellobiose octaacetate with alcoholic KOH or
columns and as catalyst carriers (Refs 1,3 & 4) by the action of some bacteria on ceHulose(Ref 1)
(See ahso numerous entries in CA’s) Re/s: l)Beil 31, 380-1 2)OrgSynth 17(1937), 34 &
The use of Cellite as component of inert COIIVO1 2(1943), 122
simulants for HE ‘s, was investigated at PicArsn. Cellobiose Octa&etates, C2eH3e01 ~. Its
A mixt contg Celite 10 & crude or semi-refined a-isomer, ndls or Iflts(from ale), mp 220-20, can
polychloronaphthalene was found to be suitable be prepd by treating dry absorbent cotton with
for that purpose(Ref 2) AC20 contg some coned H2S04(Ref 2), or by
The term Celite is also applied to a soln other methods(Ref 1). The ~-isomer, ndls(from
of dicalcium silicate & dicalcium alurhinate ale), mp ca 200°, can be prepd by heating
used in Portland cement industry(Ref 1) cellobiose with AC2 O & CH3COONa or by other
Re/s: l)Gardner’sChemSynonyms(1948), 121 2) methods(Ref 1)
A. J. Clear & O. E.Sheffield, PATR, 1618(1948) Re/s: l)Beil 31, 382-3 2)OrgSynth 17(1937), 36 &
(Inerts simulants for high expls) 3)H.Strain, COIIVO1 2(1943), 124
AnalChem 21, 77(1949 )( Use of diatomaceous earth
in chromatographic columns) 4) CondChemDict CelIobiose Nitrates. J’wo nitrates: Cellobiose
(1961), 233 Nitrate A, N content 8.45 %;and Cellobiose
Nitrate B, N content 13.7% are listed by Berl &
Celladyne, Antifrost. See Antifrost Hefter without giving any props except mol wt
Celladyne in Vol l,p A466-L of this Encyclopedia (Ref)
Re/: E.Berl & 0. Hefter, Ann 478, 244(1930) &
Cellamite. An expl contg AN 86.0, NG 12.0, NC CA 24, 4333(1930)
( 12% N) 0.5 & cellulose 1.5%. It was
investigated in 1925 by the Commission des Cellobiose Octanitrates, C , ~Hl ~N~027; mw
Substances Explosives(CSE) and found to have a 702.30, N 15.93%. TWO compds are described
CUP value(power by French Lead Block in the literature:
Expansion Test) 83% of PA and detonation Cellobiose Octanitrate o{ Asbford et al, wh
 c 94

crysts(from 2:1-ether-methanol), mp 154-5°; was Cellose. Same as Cellobiose

prepd by nitrating celloboise with nitric acid(d
1.5) in the same manner as was described in Cellosolve. Registered trade name for mono- and
Ref 2 for nitration of starch. The compd was dialkyl ethers of ethleneglycol and their derivs.
more stable than maltose octanitrate(judging by The so-called “Cellosolve” Solvent is
Abel Test), but it did not pass Bergmann-Junk Etbyleneglycol Monoethyletber or 2-Etboxyetbanol,
Test(Ref 3) H2C2.0.CH2.CH20H; mw 90.12; col Iiq,
Cel[obiose Octanitrate of Fleury et al. It is d 0.9311 at 20/200, fr p ca -70°, bp 135.1°,
claimed that it is ~-cellobiose octanitrate and n~ 1.406 at 25°, fl p 130°; miscible with w and
its structural formula is: hydrocarbons; can be prepd by heating
ethylenechloride with ethanol & Na acetate, or
by other methods; used as solvent for NC, natural

o No @ ‘.— ;02 $H2.0N02 & synthetic resins and for many other purposes
2 1/ N02 HV -–0 N02 (Refs 1-4)
C,H __). eI.. . 0. -J?’$ ‘{ There ate also Butyl “Cellosolve’‘(qv),
H “Cellosolve” Acetate(Ethylenegly col
E H2.0N02 \~N02 ~lH
H Noz Monoethylether Acetate), CH3C00.CH2CH2 .0.C2H5;
CO1 liq, d 0.9748 at 20/20°Y bp 156.4°; used as
wh crpts(from hot methanol by pptn with solvent for NC, oils and resins; Methyl
‘ ‘Cellosolve’’(Erhy leneglycol Monomethylether
3: l-methanol-water); mp 140°, expl at 287°
or 2-Methoxyethanol), H3C.0.CH2.CH20H; CO1
(Maquenne block), d 1.67 at 20°, [a]~ +22°11’
Iiq , d 0.9663 at 20/20°, bp 124.6°, n~ 1.4021
(in 6ps of acetone); very sol in acet & fairly
sol in abs ale; dec very slowly at RT and loses at 20° Y fl p 115 °F(ca 460); used as solvent for
c a 357. of its wt when heated at 100° for 20hrs. NC, celluIose acetate, synthetic resins and for
It was prepd by adding cellobiose in small purposes and Methyl “Cellosolve” Acetate

portions (with agitation) to a mixt of nitric-acetic (Ethyleneglycol Monomethylether Acetate),

acids maintained below OO. Cellobiose was CH5C00.CH2.CH2.0 .CH3; CO1 liq, d 1.0067 at
abtd by saponification with Na ethylate of 20/20°, bp 145.1°, fl p 140 °F(ca 600); used as
~-cellobiose octanitrate(Ref 4) solvent for NC, cellulose acetate gums, resins,
R e/s: l) Beil-not found 2) W. R, Ashford et al, waxes, oil and for other purposes(Ref 1-4)
CanJRes 24B, 242(1946) 3)Ibid, 25B, 155-8 Refs: l)Beil 1, 467, (244), [518] & {2069} 2)
(1947) & CA 41, 4312(1947) 4)G,Fleury et al, Hackh’s(1944), 178 3)Kirk & Ckhmer 7(1951),
MP 31, 115-16(1949) & CA 46, 1168(1952) 5) 244-5 (under GlycoIs) 4)CondChemDict( 1961),
E. P.Swan & L. D. Hayward, CanJChem 34, 234 & 468
856-62( 1956)( Denigration of cellobiose
octanitrate) Celloxylin, Commercial term for NC’s of low N
content
Cellophane. Registered trade name for the
elastic, transparent, heat-resistant, water-and Cell-Pitch Lye, It is a solid combustible
oil insol, gas-tight cellulose film obtd by pptn of material produced by evapn of spent waste liquid
viscose soln with Amm salts. It is used as a obtained from fermentation of sulfite-cellulose
wrapper or protective package for fabricated waste lyes(Ref 1). Was used in Germany as a
article s(Refs 1 & 4). Manuf of cellophane is fuel, as a binding agent and as an ingredient of
described in Ref 3 AN explosives(Ref 2)
Use of cellophane in packaging of mortar Refs: l)H.B.Landmark, ChemZtg 39, 98-9(1915)
increment chges was investigated at PicArsn & JSCI 34, 275(1915) 2)VKRp(Vereinigte
(Ref 2). “Saran” coated cellophane has not Koln-Rottweiler Pulverfabriken}, GerP 303980
proven to be entirely satisfactory, but appeared (1917) & JSCI 41, 199A(1922)
that laminates of pol yethylene with cellophane
would probably be greatlY superior to any single Cellular Explosives of Low Density. A
film or coated film water-stable, closed-cell, foamed-in-place
Refs: l)Hackh’s(1944), 178 2)R.Bostwick, PATR exP1osive prepd by mixing a soln of HE(such as
1621 (1946) 3)Kirk & Othmer 3(1949), 280-91 TNT, PETN, RDX, etc) with a resin [especially
4)CondChemDict( 1961), 234 a mixt of polyesters of ethyIenegIycoI and

——— —-.-—.
 c 95

maleic anhydride and mono- or poly(methyl- processing. It is intended for use as wads and
m ethyl acrylate) ] and bubbling with air in a spacers in ammo b)Composition B Cellulose
blowing chamber; then running the mixt into Nitrate Plastic shall be manufd from NC(not less
molds and curing. Alternatively 10-30% by VOI of than 11% N) 72 to 78 & camphor 28 to 22% with
them blowing agent, such as diazoaminabenzene solvent sufficient for processing, In the dry
or toluene diisocyanate is added and the mixt product, used as discs of various thicknesses,
is foamed and moIded at ~ 120° . These the mineral ash content shall be not higher than
expl foams are claimed to be useful in conjunction 1%, and residual solvent from 0.83 to 5.0%,
with high-density HE in floating mines, torpedoes, depending on thickness of the disc
etc The tests for these compns are described
Ref: H. J.Stark, USP 2845025(1958) & CA 52, in Ref 12
17716(195 @ Re/s.’ l)Daniel(1902), 119-25 la) J. J. TriHat, CR
191, 654-6( 1930)( Structwe of Celluloid) 2)
Cellular Materials, Burning Characteristics of, Marshall 3(1932), 215 3)V.H.Reed, PATR 607
are discussed in US ButMines Y Report of (1935) 4)Thor~ 2(1938), 443-56 5)Davis(1943),
Investigation RI 4777(1951), 16pp 257-8 6)Ullmann S( 1954), 141-56 7)PYROFAG,
GerP 953416(1956) & CA 53, 10766(1959)
Cellulodine. A mixt of NC with a small amt of [A smoke-producing device consisting of a
cellulose was proposed by Marga in 1895. This burnable core(such as Celluloid) and a smoldering
mixt when treated with a volatile solvent for NC cover(such as paper impregnated with saltpeter)]
produced a jelly which was less viscous and 8)Sax(1957), 447 9)Rohm & Haas GmbH, GerP
easier to work than one contg only NC. The 964985(1957) & CA 53, 22948( 1959)( CeIluIoid
product was recommended for use in blank -like substances obtained by plasticizing NC
cartridges wirh dicycIopentadenones) 10) Directorate of
Refs: Daniel(1902), 119 Materials and Explosive Research and
Development, GtBritain, Report Nos PL/58/6 &
Celluloid(zylonite or Xylonite). A proprietary pL/58/7, “CelIuloid in Ammunition”, Ott-Nov,
product patented in 1870 by Hyatt Bros of 1958(Conf) ll)CondChemDict( 1961)~ 235 12)US
Newark, NJ(Ref 5). Celluloid consists Military Specification MIL-C-1556(BuOrd),
essentially of a solid soIn of NC(with ca 11% N) Csllulose Nitrate-PIastic( Celluloid or
and camphor(or its substitute)$ with or without a PyroxyIine Type)(for use in Ammunition)
coloring matter. The product may be molded into
differently shaped articles(such astool handles, Celluloidine(Poudre cellulo~que). Smokeless
containers, combs, toys, discs, etc), using proplnt patented by Turpin in 1888 was prepd by
pressure and elevated temps. Props of typical gelatinizing pulped NC with the least amt of a
Celluloids are: d 1.35-1.60, tensile strength volatile solvent(such as ethyl acetate) and
5000-1000Opsi, ignition temp 320-380°F(160 spreading the resulting paste, in a thin layer, on
-1930), molding temp 18 5-250 °F(85-1210)(Ref a large plate placed in a drier. Then the nearly
11). It is highly flammable and explodes when dry thick sheet was removed, passed thru rolls
confined. Manuf of Celluloid is described in and cut into small cubes
Refs 4,5 & 6; its toxicity is unknown(Ref 8). Re/s: l)CundiU(1889) in MP 6, 107(under
Its stability and tests are discussed in Ref 2 Turpin) 2)Daniel(1902), 125
Some older foreign proplnts resembled, in
their compns, Celluloid(see under Camphor). Use Cellulosa. The name given by C.G.B jikkmann to
of Celluloid as bottom closing screw disc for the product obtained by nitration of 3parts of pea
time fuzes is described in Ref 3 and a smoke flour with mixed acid consisting of 10ps H2S04
-producing device in Ref 7. Uses of Celluloid in & 5ps HN03. This product was used in so-called
some Brit ammo are discussed in conf Ref 10 B j6rkmann Explosives
The following two “Celluloid - Type” R e/: Daniel(1902), 72(two bottom lines) & 125
compns are used in US for military purposes
(Ref 12): a)Composition A Cehlose Nitrate CELLULOSE AND DERIVATIVES
Plastic shall be manufd from NC(ca 11% N) ca Cellulose, (C6Hto0~)n; mw (162.14)X, d 1.27
3parts, camphor ca lpat, urea 0.75 i 0.05% of -1.61; a white, polysaccharide occurring in all
dry wt of NC and solvent in amt sufficient for vegetable tissues & fibers. Its fundamental
 C 96

composition corresponds to that of glucose cotton fibers rather than fibers slurried in
anhydride. The cellulose molecule may be liquor(Ref 51). Ardashev(Ref 11) made a study
represented as a polymer of glucose-residue of the chemical delinting of cotton seed & of
units linked in a chain: the industrial utilization of lint so obtained.
Studies on the use of other materials as
substitutes for cotton have been reported by
Schwarz(Ref 3), Morin(Ref 6) and many other
investigators
Cellulose is insol in w, ale, eth & all
known simple org SOIVS. The best SOIV for it is
L cuprammonium hydroxide, [Cu(NH~)4(OH)21 ,
-!
Th–e exact length of the cellulose molecule is also called Schweitzer’s Reagent. It is also sol
not known but it is variable and very large. in a coned soln of Ca thiocyanate alone or in
Cellulose threads possess micellar structure and combination with formaldehyde. Other SOIVS &
cons ist( according to x-ray diagrams) of numerous gelatinizes for cellulose include: zinc chloride
rod-like crystallites$ which are oriented with (in 40% soln & on heating), basic beryllium
their long axis parallel to the thread axis, perchlorate, 84% phosphoric acid, selenic acid,
forming a fiber arsenic acid, suIfurous acid, 66% HBr, 70-75% HF,
Almost pure cellulose is found in pith, coned HI, chloral with pyridine, chloral hydrate
absorbent cotton & in some filter papers, Pure in H2S04, and inorg salts(such as NaCl) in coned
cellulose is most readily obtd from cotton by solns & at high temps. Coned solns of NaOH at
treating it with dil alkalies & acids and ca -10° only partially dissolve cellulose while
thoroughly washing. with water. Another source the remainder is swelled & ~‘mercerized”.
of cellulose is wood(mostly coniferous) which Sulfuric acid in concns of 60% & above dissolves
contains 50-60% cellulose; and straw(mostly cellulose, converting it into sulfates; when
cereal) which contains 30-40%. A common treated for only a short time with H.$04, the
classification of cellulose is based on their cellulose is “ ‘parchmentized’’ (Ref 23,pp 150,
soIubilities in aq alkalies: If cellulose is 179,187 & Ref 44,p 362ff)
treated with NaOH soln of ca 18% at 20°, it The physical & chemical props of cellulose
will swell and much of the material, which is of have been detd & reported by a number of
short chain length, will dissolve. The residue investigators. For this info the refs listed
from this treatment is called alpha cellulose. should be consulted
When the soln of shorter chain lengths, called Since cellulose contains 3 active
hemicellulose, is acidified, part wiIl hydroxyl groups in each glucose anhydride unit,
precipitate. This is called beta cellulose. The many substances react with it producing esters &
remainder of substance, soluble in water, is other compds. These reactions are sometimes
called gamma celIulose (Refs 20,54 8Z 60)(See aLso accompanied by destruction of the fibrous
Refs 4,5,26,28 & others listed) structure: nitric acid, in concns above 75%,
Olsen(Ref 14a) described the prepn of forms NC suitable for the prepn of lacquers,
refined wood pulp having alpha cellulose artificial silky celluloid & propellants(See also NC
content up to 99%. This pulp approximated in or Cellulose Nitrate); acetic anhydride, in the
its characteristics those of cotton Iinters, and was presence of HZSO ~, converts cellulose into a
used for nitration to NC, Cellulose from reeds & mixt of di- and tri-acetates which are used for
other annual pIants was investigated by the the prepn of acetate rayon & as moderants for
Soci~t6 Franfaise de la Cellulose(Ref 29) as a some propInts; diIute mineral acids convert
possible raw material for prepn of military grade cellulose to “hydrocellulose” & finally into
NC. Eskridge(Ref 48) patented a process for d-glucose; oxidizing agents such as chromates,
the production of alpha cellulose from cottonhull bichromate, permanganates, bleaching
fibers by digesting the fibers at 116° with an substances, bromine water & others form a
alkali soln contg 1.6% NaOH & other chemicals. product called { ‘hydrocellulose” & “oxycellulose”;
A continous process for producing chemical-grade coned formic acid produces cellulose formate
cotton from Iinters was reported by Hercules (Ref 23,P 316); many aliphatic & aromatic acids
(Ref 50). What’s unique about the Hercules’ produce esters of cellulose(Ref 23, 345-76);
process is that digestion is carried out on moist some alkyl chlorides or srd{ates when heated with

—.—-_ ~_. —
 c 97

cellulose in an autoclave produce ethers of Edit, “Rogers’ Industrial Chemistry”, Van

celhdose (Ref 26,p 311 & Ref 23,p 377); Nostrand, NY(1 942), 1441-56 18)R.B.Barns &
various nitrogetz-contg substances are used to C .J .Burton, IEC 35, 120-5(1943)(Electron
prepare, by indirect methods, aminocellulose microscope ~d cellulose) 19)E.Ottj 4‘cellulose
(Ref 23,P 423-38); phenyl isocyanate reacts with and Derivatives”, Interscience, NY(1943)
cellulose to produce the celluIose phenyl ester 20)Hackh’s(l 944), 178 21)N.Gral~n,
of carbamic acid(C6H~ .NH.CO0.CQH904); and ‘ ‘Sedimentation and Diffusion Measurements on
a viscose soln, treated by the method of CelluIose and Cellulose Derivatives”, Almqvist
Lilienfeld, produces cellulose thiourethanes & Wiksells, UppsaIa(1944) 22) E. Heuser, ‘ ‘The
(Ref 23,p 440) [See also Cellulose Derivatives & Chemistry of Cellulose”, Wiley, NY(1944) 22a)
Cellulose Nitrate(NC) described below] Collective, MSCE 31, 238(1944) & 33, 107(1947)
Uses, CelIulose is the most important (Refining of linters) 23)J .T.Marsh & F. C. Wood,
industrial org raw material in the world, and ‘ ‘An Introduction to the Chemistry of CelluIose”,
unlike mineral wealth, the supply is replenishable Chapman & HaII, London(1945) 24)R.N.Shreve,
continuously. It is the basis of the textile & ‘ ‘The Chemical Process Industries”, McGraw
paper-making industries. When nitrated, cellulose -Hill, NY, 1st edit(1945), pp 445,743,758 & 2nd
yields NC used in proplnts & expls, collodion, edit(1956)Y pp 454, 783 25)P, H. Hermans,
‘ ‘celluloid” ~ pyroxylin Iacqures, and a variety of “Contribution to the Physics of Cellulose
miscellaneous products Fibres”, E1sevier, NY( 1946) 26)C.Dor<e, “The
The requirements of the US Armed Forces Methods of Cellulose Chemistry”, Chapman &
for cellulose used in various military applications Hall, London(l 947) 27)J .M.Matthews et al,
are given in the specifications listed as Ref 61 “Textile Fibers”, Wiley$ NY(1947), pp 99-450
Refs: l)Beil 31, 446(Compd from sucrose) 2) 28)The Svedberg, JPhCollChem S1, 1-18(1947)
M. Cunningham & C.Dor~e, JCS 1011, 497-512 (The cellulose molecule) 29)Soci6t4
(1912)(Action of ozone on cellulose) 3)R. Fran$aise de la Cellulose, BritP 591072(1947) &
Schwarz, MAF 1, 229(1922); JCSI 38, 602 A(1919); CA 45, 859(1951) 30)G.Champetier, ‘ ‘D~riv~s
OstChemZtg 22, 50-2, 57-60(1919) & CA 13, Cellulosiques”, Dunod, Paris(1947), 1-37 31)
3317( 1919)( Cotton & its substitutes for manuf L. Brissaud, MSCE 33, 75-98 (1947 )(Detn of
of NC) 3a) E. Worden, “Technology of Cellulose pentosanes in plant materials & in pulp) 32)
Esters”, VanNostrand, NY, VOI I, Part 1(1921) Collective, MSCE 33, 99-106( 1947) (Refining of
4)C.Birtwell et al, JTextInst 14, 305 T(1923) & pulp from wood) 33)G.Petitpas, MSCE 34, 125
CA 18, 171(1924)(Chemical analysis of cotton) 5) ( 1948)( Reaction of cellulose with aIkalies) 34)
A. B. Corey & H, LeB.Gray, IEC 16, 853, 1130 T. Petitpas, MSCE 34, 139(1948)(Variation of
(1924) tk CA 18, 2805(1924); CA 19, 575(1925) structure of celluIose in alk soIns) 35)A.
(Preparation of standard NC) 6)G.Morin, Mp 22, Br6guet et al, MSCE 34,149,153(1948)
57( 1926)( Niwation cellulose derivatives) 7)AcW0 (Absorption of NaOH by native ceIlulose & by
Schorgert “The Chemistry of Cellulose and Wood”, regenerated viscose cellulose) 36) E. Calvet,
McGraw-Hill, NY(1926) 8)K.Hess, “Die Chemie MSCE 34, 163-77( 1948 )( Mercerization of cellulose
der Zellulose und Ihrer Begleiter”, Akademischen by NaOH) 37)J.Chastaignet, MSCE 34, 255
Verlag, Leipzig(1928) 9) L. Brissaud, Mp 25, ( 1948)( Extraction from wood by org SOIVS) 38)
476-530( 1932-33 )(Degradation of cellulose by dil A. Roudier, MSCE 34, 263(1948)(Extraction of
HC1) 10) H. Mark, c‘Physik und Chemie der cellulose from wood by org SOIVS) 39)A.
Cellulose”, Springer, Berlin(1932) ll)B.T. Roudier, MSCE 34, 273( 1948) (Refining of
Ardashev, IEC 25, 575-81(1933) 12)M.Battegay s cellulose) 40)K.Tamaru, JChemSocJ apan 69,
L .Denivelle, “La Cellulose”, Hermann, Paris 20-2(1948) & CA 46, 8849(1952); BullChemSoc
(1934-35) 13)0. Faust, Edit, “’CeIluloseverbindun- Japan 24, 164-8(1951) &CA 47, 305(1953)
gen”, Springer, Berlin(1935) 14)Thorpe (Combustion of cellulose in presence of inorg
2(1938), 456ff 14a)F.Olsen, IEC 30, 524(1938) salts) 41)Kirk & Othmer 3(1949), 342-56 & 4
15)C.G.Schwalbe, “Die Chemie der H61zer”, (1949), 563 42)p.H.Hermans, “phYsics and
Borntraeger, Berlin(1938) 16)E.Sutermeister, Chemistry of Cellulose Fibers”, ELsevier, NY
‘ ‘Chemistry of Pulp and Paper Making”, Wiley, NY ( 1949) 43)0. Pfeiffer & D.Krfigger, ‘ CBeitr&ge
(1941) 17)0.Eisenhut & E.Kuhn, AngChem 55, zur Oxydation von Cellulose mit Stickstoffdioxyd’ ~
198-206(1942).(Microscopic investigation of native Verlag Chemie, Weinheim(1949) 44)Karrer
& artificial cellulose fibers) 17a)C.C, Furnas~ (1950), 362ff 45)K.H.Meyer et al, Monatsh 81,
 C98

151-4( 1950) &CA 44, 8639( 1950)(Solution of also important that the deriv preserve the high
cellulose in org SOIVS) 46)H.F,Mark & A.V. molecular structure of the cellulose chain,
Tobolsky, “Physical Chemistry of High Polymer otherwise the product will represent not
Systems”, Interscience, NY, vol 2(1950) 47) cellulose, but a degraded carbohydrate deriv
R.S.Jessup & E. J. Prosen, JRNFS 44, 387-93 (Ref 4). Spurlin(Ref 5) has considered the
( 1950)( Heats of combustion & formation of reaction of cellulose & its derivs in various
cellulose & cellulose nitrate) 48)J .L.Eskridge, reaction media: such as l)homogeneous systems
USP 2536o45 & 6(1951) & CA 45, 2668(1951) 49) 2)two-phase systems in which cellulose is
L. E.Wise & E.C. Jahn, “Wood Chemistry”, amorphous and 3)two-phase systems in which
Reinhold, NY( 1952) 50)Anon, ChemEngrg 61, cellulose is partially crystaHine(See also Ref 7
116-8(May, 1954) 51)W.E.Segl, USP 2673690 & others above)
(1954) & Official Gazette USPO 680, No 5, Some reactions and derivs of cellulose are
1279(30 Mar, 1954) 52E.Ott, H. M. Spurlin & M.W. given under Cellulose(above). The derivs of
Grafflin, “Cellulose and Cellulose Derivatives”, interest in the expl industry and allied
Interscience, NY, VO1 5, p-t 3(1955) 53)K. applications are included here:
Ward, Jr, Edit, “The Chemistry and Chemical Cellulose Acetates or Acetyl Cellulose
Technology of Cotton”, Interscience, NY( 1955), are esters of cellulose & acetic acid$ and are
782PP 54)E! .B .Thomas, “The Production of the most widely known org cellulose derivs; they
Chemical Cellulose from Wood”, JChemEduc 35, are used expensively in industry under a variety
493( 1958) 54a)J .Grant, “Cellulose Pulp”, of trade names. Olsen et al(Ref 3) proposed that
L. Hill, London(1958), 540PP 55) J. Honeyman, AC’s be used as deterrents in priming compns,
Edit, t ‘Recent Advances in the Chemistry of and Preckel(Ref 8) patented their use as an
Cellulose and Starch” ~ Inters cienceY NY( 1959), inhibitor film on large-grain smokeless proplnts.
358Pp 56) J. A. Gascoigne & M. M. Gascoigne, There are also numerous applications of CA’s in
‘ ‘Biological Degradation of Cellulose”, textiles & plastics used in ordnance. The
Butterworth, London(1960), pp 1-30 57)H. specification requirements for AC’s used in
Staudinger, c‘Die Hochmolekularen Organischen proplnts are given in hm-C-20301. See also
Verbindungen, Kautschuk und Cellulose”, Vol l,p A5 5-R under Acetyl Cellulose for addnl
Springer, Berlin( 1960) 58)Consultants Bureau info on AC’s
Enterprises Inc, t ‘Soviet Research on the Cellulose Acetate Butyrates, wh flakes or
Swelling of Cellulose Materials, 1949-1956”, granules, similar to cellulose acetate and
English Translation, NY(1960) 59) J. P. Casey, similarly converted into plastic films, sheets
“Pulp and Paper”, Interscience, NY, Vols 1-3 & molded objects(Ref 9). See Specs MIL-C-55 37A
( 1960-61) 60)ConChemDict( 1961), 235 61) (1) & JAN-C-590
UsSpecifications Ml L-C-206 (Cotton cellulose for Cellulose Acetate Nitrates. See Nitroacetyl-
use in expl); MiL.C-216 [Wood pulp(sulfite) celluloses, Vol l,p A56-L
cellulose for use in expls ] ; and MI L-C-677 Cellulose Acetorzitrate, C, *H1 ~(N02)2(COCH~)4.
(Cellulose, regenerated, strip for use in primer This product & other acetonitrates, contg
vent seals of small arms ammo) varying amts of N02 & AC groups, were claimed
to be prepd by Atsuki(Ref 1) by acetylating NC
Cellulose Derivatives [Except Cellulose Nitrate with acetic anhydride & glac AcOH in presence
(NC)] . Cellulose, as a polyhydroxy alcohol, of H2S04. The flammability of the product was
offers the possibility of reacring with many much lower than that of NC$ but its tendency
substances to produce a variety of compds. The to decompose spontaneously was the same as
course of the reaction and props of the derivs that of NC
depend, to some extent, on the condition of the Cellulose, Aminated. See Aminated Cellulose,
original cellulose. It may have been modified by Vol l,p A172-L
hydrolysis, by oxidation, or by regeneration. Cellulose, Aminate4Acetate Esters). See
Derivatives are prepd usually with the objective Aminated Cellulose Acetate Esters, Vol l,p A 172-L
of obtg physical props, representing an improve- Cellulose, Aminoetbyl. See Aminoethylcellulose,
ment over cellulose itself. Therefore, treatments Vol l,p A203
which result in only slightly modified cellulose, Cellulose, Aminoetbyl(Nitrate). See
yielding no greatly changed physical props, are Aminoethylcellulose Nitrate, Vol 1,p A204-L
of comparative little interest to industry. It is CelluIose, Aminoetbyl(Perchlorate). See
 c 99

Aminoethylcellulose Perchlorate Vol l,p A204-R cellulose prepd from cotton wastes or suitable
Ce~lujose Benzoates are esters of ce]lulose& short-fibered commercial cotton and shall be free
benzoic acid. The mono-and di-benzoates were from foreign matter of any kind. Cotton Iinters
ptepdby treating cellulose in alk soln with may be used when specified in the contract or
benzoyl chloride. Tri-benzoate was reported to order b) The material shall be prepd for nitrating
have been prepd by the action of benzoyl by purifying and thoroughly washing with water
chloride & pyridine on cellulose at 110-300 in c)Moisture(max 7.0%)- by loss of wt after drying
the presence of nitrobenzene. The prod is sol at 105° d)Alkali sol matter(max 5.0%)- by
in chlf & nitrobenz(Ref 6) extracting cellulose with 7.14% NaOH soln,
Cellulose Berzzoates(Nitrates). Set-do & Kondo washing the residue successively with water, alc
(Ref 2) treated cellulose monobenzoate at 18-20° & eth, drying at 1050 and weighing e)Ether
with mixed acids of different percentage compn extractive matter(max 0.4%)- by extraction with
and obtd cellulose mononitrate- & dinitrate ether, drying the residue at 105° and weighing
mononitrobenzoate. The expl props of these f)Ash(max 0.5%)- by igniting a sample moistened
nitrates are similar to those of normal NC, but with 70~ nitric acid soln until the combustible
they are more stablej less hygro, less sol in matter has been consumed, cooling in a
eth-ale, and burn at a slower rate than NC desiccator and weighing g)Viscosity(3 to 9
Cellulose Nitrates. See folIowing item, poises for Grade 1 cotton and 10 to 36 for Gde
discussed separately II)- by falling sphere method using soln of
Cellulose Triacetate. See Acetyl Cellulose, cellulose in cuprammonium h) Lime(max, trace)- by
Vol l,p A55-R pptn of Ca ion with Amm oxalate soIn i)
See also Ethyl and Methyl Cellulose Chlorides(max, trace)- by pptn of Cl ion with Ag
Refs: l)K.Atsuki, JFacultyEngTokyoImpUniv nitrate soln j)Sulfates(max, trace)- by pptn of
15, 309-16(1915); CA 19, 1626(1925) & .$S 20, S04 ion with Ba chloride soln k)Hypochlorites
140( 1925) 2)M.Sendo & J .Kondo, CelluloseInd (max, trace)-by KI soln(lt violet coloration)
(Tokyo) 6, 150-5(1930)& CA 25, 11668(1931) 3) l)Absorbency- by rolling ca Ig sample into a
F. Olsen et al, USP 2001212(1935) & CA 29, ball and placing it lightly on the surface of 200ml
4586(1935) 4)C.J.Maim & C. R. Fordyce, of w in a 250ml beaker. The ball must sink below
“Cellulose Organic Acid Esters” in the surface within 3secs
“Cellulose and Cellulose Derivatives”, E.Ott, US military requirements and tests for
Edit, Interscience, NY(1943), 667ff 5)H.M. wood pulp(sulfite) intended for manuf of NC are
Spurlin, {‘Kinetics and Equilibria Involved in as follows(Ref 8): a)The material shall be
Cellulose Reactions”, Ibid 6)Dor6e( 1947), 301-2 bleached sulfite pulp from coniferous wood which
7)G.Champetier, CgD6riv~s CelIuIosiques”, has been washed to remove the purifying chemicals
Dunod, Paris(1947), 275pP 8)R.F.Prekel Usp and formed into sheets or laps suitable for
2549005(1951) & CA 45, 10590(1951) 8a)Faith, fluffing or shredding and subsequent nitration.
Keyes & Clark( 1957), 242-6(Manuf of cellulose The material shall be free from foreign matter of
acetate) 8b)W.D.Paist, “Cellulosics”, Reinhold, any kind b)Moisture(max 10.0%)- by loss of wt
NY(I 958)( Applicatiorrs of chemical products from after drying at 105° b)Weight- 0.525~0.l 25OZ per
cellulose) 9)CondChemDict( 1961), 236 10)US sq ft per O.O~n thickness c)Thickness-
Spec MIL=C-20301 (Cellulose acetate for use in o.045400~5+0.OIQ d)Alpha-cellulose( min 95.07. for
proplnts)
Grade A pulp and 90.0% for Gde B)- by treating a
sample of cellulose with 17.5% NaOH soln,
Cellulose and Its Esters(Except Cellulose
filtering, washing the residue, drying it ar 105°
Nitrate) Analytical Procedures. Tests for
and weighing e)Beta-cellulose( max 4% for Gde B)
cellulose used in industries other than manuf of
-by acidifying the filtrate of previous operation
expls & propln ts are described in Refs I-6.
with glac AcOH, heating to coaguIate the
Tests for cellulose acetate, cellulose acetate
beta-cellulose, allowing ppt to settle, fitering,
butyrate, ethylcellulose and methylcellulose are
drying and weighing f)Gamma-celhdose( max 6.o%
given in Ref 6, Methods D8 17, D871, D914 &
for Gde B)- by subtracting from 100 the sum of
D 1347
percentages of alpha- and beta-celluloses g)
US military requirements and tests for
AlkaIi soluble matter(max 7.0% for Gde A & 15.0%
cotton intended for manuf of NC are as follows
for Gde B)- same procedure as for cotton h)Ether
(Ref 7): a)The material shall be bleached
extractive matter(max 0.20% for Gde A & 0.40%
 c 100

for Gde B)- same procedure as for cotton i) Ash Nitrocellulose( NC), more properly called
(rnax O.30% for Gde A & 0.50% for Gde B)- same ( ‘cellulose nitrate”, is the oldest deriv of
procedure as for cotton j) Lime(max 0.05z for cellulose and the only inorg ester which has
Gales A or B)- by Amm oxalate soln k) Chlorides attained coml importance. Assuming a
(max, trace)- by Ag nitrate soln I)Sulfates- by Ba C6H, oO~ unit for cellulose, any NC may be
chloride soln m)Hypochlorites(max, trace)- by written as C6H7(OH)x(ON02)y,where x+y = 3. If for
KI soln(lt violet coloration in presence of trace theoretical purposes the average number(y) of
of hypochlorites) n)Viscosity(8 to 17 poises)- by nitrate groupings for CG unit is required? it can
falling sphere method, using soln of cellulose in be calcd from the relation:
cuprammonium
162N
US military requirements and tests for ~ where N is percentage of
regenerated cellulose in strips ca 0.5” wide and ca y= 1400-45N
0.006” thick for use in primer vent seals for small nitrogen found on analysis. Thus a product
arms ammo are described in Ref 9 contg on-the average one ‘nitrate grouping per
US military requirements and tests for CG will contain 6.76%N, two groupings 11. ll%N
cellulose acetate, cellulose acetare butyrate and and three groupings 14. 14%N(Ref 59,p 233 &
ethylcellulose are given in Refs 10, 11 & 12. Ref 73a, pp 25-6)
There is no US military specification for With the exception of trinitrocellulose,
methylcellulose however, the above NC’s do not represent
Re/s: l)Kast-Metz(1944), 22-53 (Various tests for stoichiometric compds, since no homogeneous
cellulose) 2)Dor~e(1947), 10-39 42-72( Various reaction product composed of a single
tests for cellulose) 3)OrgAnalysis 1(1953), 32 & individual mono-or dinitrocellulose has been
54-5(Some tests for cellulose) 4)Ott 5, Pt 3 obtained. The nitrate groups are distributed
(1955), 1357-92(Various tests for cellulose) 5) along the entire length of the cellulose chain
OrgAnalysis 3(1956), 479( Cellulose derivs, according to the laws of chance and the
characterization) 6) ASTMStds(1961): Method reactivity of hydroxyl groups. Depending on the
D1343(Viscosity detn of cellulose derivs by conditions of esterification, a NC of any desired
falling ball method; D1348(Moistute detn in N content may be obtained. The name ‘ ‘cellulose
cellulose); D1696(soly of cell in NaOH solns); nitrate”, or t ‘nitrocellulose” ~ therefore does not
D1795(Detn of intrinsic viscosity of cell refer to a single stoichiometric compd, but it is a
dissolved in cuprammonium hydroxide soln by generic term denoting a family of compds(Ref
employing a capillary-type viscometer); D1 915 73a, p 26)
(Chromatographic analysis of chemically refined In older literature, especially the European,
cellulose); D817(Tests for cellulose acetate before the polymeric nature of cellulose was
butyrate); D871 (Tests for cellulose acetate); definitely established, its unit was assumed to b e
D914(Tests for ethylcellulose); D1347(Tests C24H2808(OH)1 ~ and its nitrated products were
for methylcellulose) 7)US Joint Army-Navy called dodecanitrate ~ endecanitrate etc. Since
Specification JAN-C-206; Cellulose, Cotron(For these terms are still found in some literature,
Use in Explosives) 8) JAN-C-216; Cellulose, their meaning is given in the following table:
Wood pulp(For Use in Explosives) 9) JAN-C-677; NO
Cellulose, Regenerated Strip(For Use in Ammu- Cellulose Formula Molecular Nitro- per 1 g
nition) 10)US Military Specification MIL-C-20301, Weight gen, % NCt
in cc
Cellulose Acetate(For Use in Propellants) 11) —..— ...—..— —... .— -
MIL-C-5537A(1 ), Cellulose Acetate Butyrate(For Dodecanitrate C24H280a(ON02)12 1188.56 14.14 -–
Use in the Manufacture of Organic Protective Endecanitrate C24H2909(ON02)1, 1143.56 13.47214
Coatings) 12)MIL-E-1 0853 B(Ethylcellulose)
Decanitrate C24H30010(ONC)2),0 1098.56 12.75203
Enneanitratt C24H310,1(ON02)9 1053.56 11.96 190
CELLULOSE NITRATES or NITROCELLULOSES
(NC’s)(called Nitrocellulose, Coton-poudre or Octanitrate C24H320,2(ON02)~ 1008.56 11.11 178
Pyroxyline in Fr; NitrozeHulose in Ger; I-ieptanitrate C24H33013(ON02)7 963.56 10.18 162
Nitrocellulosa in Ital; Nitrokletchatka, Piroksilin
Hexanitrate C24H34014(ON02)6 918.56 9.15 146
or Nitrotsellulosa in Rus; Nirrocelulosa or
Piroxilina in Span; and Sh5kamen in Jap)(See Pentanitrate C24H3~01 ~(ON02)5 873.56 8.02 128
addl foreign names under specific types of NC). T etranitrate C24H~60,6(ON02)4 8.2g.56 6.76 108
 c 101

the Preparation and Treat ment of Gun cotton”

(See also Ref 51,P 367)
that claimed the process of converting. NC into a
As the nitration of cellulose is a
pulp in the same manner as practiced in making
heterogeneous reaction involving irregular
paper. Abel showed thru his process of pulping
esterification of some or all OH groupsy the
& pressing NC into sheets, discs, cylinder &
attributing of definite formula to products of
other forms, and thru further researches that the
nitration is not necessarily valid. The N
stability of NC was greatly improved. Sihortly~
content of any particular NC largely defines its
thereafter, E ,A.Brown, asst to Abel, discovered
SOly & other props~ and consequently its
industrial application. A summary of the types that dry compressed NC could be made to
detonate violently by a MF detonator such as
of NC’s used in industry is as follows(Refs 43 &
Nobel had used for NG. Then, a further
59)
discovery was made that wet, compressed NC
could be exploded by a small quantity of dry NC
Nitrogen, % Solvents Uses [principle of Booster]. Thus large blocks
of wet NC could be used with comparative safety
10.7-11.2 Alcohol Celluloid plastics;
laquers and the manuf & use of NC were thereby
11.2 -11.7 Methanol; eth-ale; Photogr films, established(Ref 44)
acetone ethyl-, laquers & nitrate
buty- or amyl The next major step in the history of NC
rayon
acetates: methyl was the development of celIuloid( 1870) the first
-ethyl ke’tone -
synthetic plastic. This was followed by
11.8 -12.3 Same as above; Gelatinous expls; development of the NC Iacquer industry which,
in saluble in films; Iaquers;
alcohol srtifical leather following WWI, expanded greatly(Ref 43)

12.4 -13.5 Acefone; partially Propellants &

sol m other solvents explosives Properties of NC’s. See under Collodion Cotton ,
Pyrocellulose, Blend and Guncotton

Historical (Ref 3). The history of modem expls

Preparation of NC’S. Cotto% one of the purest
began with the discovery of NG & NC. At about
forms in which cellulose occurs in nature, had
the time that A .Sobrero first prepd NG, during
been used(up to WWII) as the chief source for
1845-47, C. F.Scti6nbeim at BaseI and R. Bottger
the prepn of NC. Efforts have been made also
at Frankfort-on-the-Main independently nitrated
to find other sources of cellulose, such as wood
cotton; they perceived the possibilities of the & other plants, suitable for nitration. The pres-
prod and later cooperated to exploit its use in ent major sources of nitration grade cellulose
expls. Earlier in 1833, Braconnot had nitrated
are sulfite & sulfate wood pulps. Although
starch; and in 1838 T.J .Pelouze continuing the
HN03, in both liq & vapor form, and mists of
experiments of BraconnotY also nitrated paper,
HN03 with a variety of other chemicals have
cotton & various other materials but did not
been used experimentaly to nitrate cellulose, the
realize that he had prepd NC. With the announce-
industry to-day and for over a century still
ment by Schonbeim in 1846, an d in the same
empIoys HN03-H2S04 acids as nitrating agent.
year by B ottger that guncotton had been prepd,
In contrast to other reactions, in which cellulose
the names of these two men soon became
dissolves & its original fibrous structure is Iost,
associated with the discovery & utilization of
nitration is effected with retention of its fibrous
NC. However, the published literature, at that
structure, except that some swelling of fibers
time, contains papers by several investigators on
might take place
the nitration of cellulose, before the process of
Schi$nbeim was known. Among these were paper For explanation of the process of nitration
by Dumas and Pelouze, and Prof Otto of Germany. two theories were advanced. Accdg to the 1st of
Other names associated with the prepn of NC these, the reaction proceeds in topochemical
are those of Berzelius, Taylor, Dr Knopp of fashion, whereby the nitrating reagent diffuses
Leipzig, Teschemacher, Gladstone, Crum, von progressively from the outside to the interior of
Lenk of Austria, and others up to 1852(Ref 44) the fiber, so that the chains on the surface are
A patent by Tompkins in England mentions, nitrated first. Accdg to the 2nd theory, the
in 1862Y the use of “pulped guncotton” but makes nitrating reagent pen etrates uniformly in all parts
no claim to invention of the pulping process. It of the cellulose fiber, and the reaction proceeds
was Abel’s patent of 1865 on “Improvements in quickly thruout the whole micellar system in
 c 102

permutoidaI manner(Ref 73a,pp 26-9 & Ref 74,pp lab Holland type paper beater. Enough ‘Na
730-7). Aced to Miles & Craik(Ref 9a) the carbonate is added to keep the reaction faintly
nitration of NC of less than 12.5%N is a alk to phenolphthalein. Pulping is continued to
topochemical reaction whereas above this N content the desired fineness. “Poaching ‘‘ is conducted
the reaction is permutoidal by washing NC from the beater, filtering the “mixt
The extent or degree of nitration of and boiling for 4hrs with fresh w while stirring
cellulose is expressed by the nitrogen content, mechanically. From time to time a little
except in France & some other Latin countries, Na2COg soln is added to maintain the mixt sl
where the degree of nitration is expressed as alk to phenolphthalein. According to the Spec”
cc’s of ‘NO evolved in a nitrometer and measured the total boiling treatment with poaching is as
under std conditions, per lg of NC. Each follows:
O. lcc of NO corresponds to ca 0.0063%, or each 4 hrs boiling with or without Na2C03
percent of NO times 15.96 equals number of cc of
2 hrs boiling without Na2C03
NO(Ref 44,p 258; Ref 50, table 3 & Ref 51,p 367) .
It is possible to prep NC’s covering the 1 ht boiIing without Na2C03
entire range of N content, however, the products 1 hr boiling without Na2C03
normally prepd(for military applications) fall in
Each boil is followed by settling of NC & change
the range ca 10.7 to 14% as shown in table
of w. Finally “washing” of NC is conducted
above. The products with N to ca 12.2%N are
with a min of two washes accompanied by
known as “Collodion Cotton” or { ‘Pyroxylin”.
mechanical agitation. If a sample taken after
Those with N 12.6-12.7% as “Pyrocellulose”,
the w washes gives a min of 35 minutes in the
“Pyre” or “Pyrocotton”; those with N 12.15
65.5°C Heat Test & 30 minutes in the 134.5°C
-12.25 as “Blend” or “Blended NC”; those with
Heat Test, the NC is considered satisfactorily
13.35-13.45% as “Guncotton” and those with N
stabilized. Otherwise addI washes should be
content ca 14% as “High Nitrogen NC”. The
given the NC
prepn, props and uses of various NC’s in
Industrial Manufacture o/ NC(Ref 75). For
proplnts & expls are discussed separately below
miIitary use the ind manuf of NC in the USA is
Laboratory Procedure Used at Picatinny Arsenal
carried out by the mechanical dipper process
(Ref 79). Second cut cotton linters or wood
(DuPont) which has displaced other hazardous
puIp previously dried to a moisture content of
processes. About 32 lbs of dried cotton linters
less than 0.5%, are nitrated by immersion in
or w~od pulp cellulose is added to a chge of ca
mixed acid(MA):
1500 lbs mixed acid at a temp of 30°C. The
Ratio of MA to cotton 55to 1
nitrator is equipped with paddles, so designed
Composition of MA(approx)
that the cellulose is immediately drawn below
a) for 12.6%N H$04/HN03/H20
the surface of the acid. Since the nitration
63.5/21/15.3% reaction is exothermic, the temp is kept from
b)for 13.4%N H$04/HN03/H20 rising above 34°. Addn of cellulose to the acid
68/22/10% requires about 4 reins; nitration, with agitation of
Temp of acid at start 34°c the mixt, requires 20 reins total time. The slurry
Time of nitration 24 minutes is then discharged thru a bottom valve into a
During nitration the mixt is stirred occasionally centrifuge, where most of the spent acid is
to keep the acid homogeneous. The mixt is then removed. This acid-wet crude NC then is forked
filtered on a Biichner funnel for ca 3 reins and thru an opening in the bottom of the wringer into a
rapidly drowned~ accompanied by strong hand drowning basin, where it is rapidly submerged by
stirring~ in at least 50 VOIS of cold w, contg ice. a heavy stream of w. It is now ready for the
After the NC is settled, most of the w is necessary purification process
decanted & fresh w is added. The NC-W mixt is The mixed acid used in the nitration of
boiled & the acidity adjusted to 0.25 to 0.50% as cellulose has a compn dependent upon the type
H2S04. This “sour boil” is continued for at of cellulose nitrated, the degree of nitration
least 24hrs for Pyrocellulose and at least 60 hrs desired, and the season of the year. During
for Guncotton. Addl boiling with changes of w warm weather, it is necessary that the HN03
are made in accordance with Specification content be S1 greater than during winter, because
MIL-N-244A of a tendency toward denigration of the mixed
The next operation is ‘“pulping” of NC in a acid during warm weather. Variations in mixed

——.-.———.
!
 c 103

acid compns are used also in order to obt In addn to requirements with respect to nitrogen
prodtcts having different volubility & viscosity content, NC must comply with requirements of
characteristics, Typical compns of mixed acids the 65.5°KI & 134.5 °Heat Tests. Grades A & D
are shown below: NC must not be less than 99% sol in eth-alc
mixt. Grade A(Ty pe 1)~ Gd C & Gd D NC must
Composition of Mixed Acid for Nitrating Cellulose contain not more than 0.4% ash and not more
than 0,4% material insol in acct. Other requirements
For Pyrocellulose For Guncotton
from: such as fineness & viscosity may. also be
from:
Composition, Cryton specified. Explosive & other props of military
Wood UIP C?tton Wood ulp
% Lmters Cellu f ose L Inters Cellu f ose grade NC are discussed under individual types,
below
Sulfuric acid 59.2 57.0 60.5 59.5 Uses. NC isused in single-base, smokeless
Nitric acid 21.5 23.5 24.5 28.5 propellants(NC & non-expl ingredients); double
Nitrosylsulfuric 3.5 4.4 4.0 3.0 -base, smokeless proplnts(NC & NG); triple
acid -base, smokeless proplnts(NC, NG &
Water 15.8 15.1 11.0 9.0 nitroguanidine); and in dynamites. Commercially
Removal of impurities, originally present or NC is used in pharmaceuticals, lacquers, and
produced by side reactions during nitration of photographic products(Ref 80)( For more detailed
cellulose, is accomplished by lengthy hydrolysis info on ~C’s~ see various types of NC listed in
under acid conditions% beating, poaching & wash- Table and discussed separately, next page)
ing operations. The acid hydrolysis termed
‘ ‘sour boil” ~ is carried out by treating the crude Collodion Cotton or Pyroxylin(caIled Pyroxyline
NC with boiling w contg 0.025-0,50% acid, or Collodion in Fr; Kollodiumwolle in Ger;
calcd as H$04. Pyroxylin & Pyrocellulose are Collodio or Pirossilina in Ital; Kolloksilin or
subjected to 40 hrs of boiling treatment, with 3 Piroksilin in Rus; and Colodio or Piroxilina
changes of w; Guncotton is subjected to 60 hrs in Span)(Grade D NC, according to US Military
of boiling treatment, followed by two 5-hr boiling Spe,c MIL-N-244A) NC contg 11 to 12% N, which
treatments, with 3 changes of W. J3eating, corresponds to a mixt of “octanitro- and
poaching & washing operation are carried out enneanitrocelIuloses” ~ C2 ~H3201 ~ (ON02)S to
similar to the Spec procedure given under C24H3, 0, , (ON02)9, according to earlier
Laboratory Procedue nomenclature; It-yel matted filaments or pale
yel, syrupy liq when dissolved in eth-alc(3: 1 );
Military Grades of NC, The product produced bY very flammable & dangerous, fl p ~SOOF;
the above nitration & purification process is of decompd by light; sol in eth-ale, acet or glacial
max stability. It is generally v S1 alk and AcOH, and is pptd from soln by w; when exposed
contains less than O.01% cellulose sulfate, in thin layers of solnfi its solv evaporates
which is unstable to heat & moisture. The leaving a cough, colorless film(Ref 81). When
great care taken in the purification of NC is subjected to che action of boiling water for 10
necessary since propellants made from NC contg days, it is hydrolyzed to the extent of 1.71%
even small amts of unstable impurities deteriorate (available HNOa liberated)(Ref 75)
rapidly. The US military grades of NC are as Pyroxylin was first prepd, in 1838, by
follows: Pelouze and later by other investigators who
LNitrocelltdose
—.—. .—.—— ..- —Nitrogen—.— Content nitrated paper, linen & cotton by the action of
Grade A Pyrocellulose HNOa(Ref 44). Its p;epn by nitrating tissue
Type I 12.6@0.10%N paper using mixed acid is described by Worden
Type II 12.60~0.15zN (Ref 7)
Material used for the manuf of celluloid
Grade B Gun cotton 13.35%N contains 11.0 to 11 .2%N~ while that used in
(minimum) B lusting Explosives has a N content of
Grade c Blend 11.5-1 2%. Military P yroxylin contains
Type I 13.15740 .05zN 12.2@ 10%N(Ref 75)
Type H 13.25 %@.05%N TWO kinds of NC ‘S were used in France
Grade D Pyroxylin 12.20~0.10%N during WWI: Coton-Poudre No 1 (CP, ), insol in
Grade E 12.00 f1.10%N eth-alc & contg ca 13%N; and Coton-Poudre
 Table Vlll

Thermochemical Properties of Nitrocellulose (Compiled from Information Supplied by E. Costa & R. Trask of PicArsn)
Nitrocel- :lpirjl:l Mo 1 OB OB Den- Heat of Heat of Gas Mean Heat COVO1- Relative
~t. % N Sity, Combstn E xp ln(at VOIUIIIe, Capacity, ume ins EnerW,
lulose(NC) (at const VO1), const VOI), moles/g c#g/deg /lbt 10) cal/g(ll)
:0, :0~ 2+ g/cc
% cal/mole (6) cal/g (7) (g)

Collodion CGH8N209 252 11.1 -6.3 -44.5 1.653 657000 734 0.04390 0.?545 29.61 -27
Cotton(l)
Collodion CeH7 ~8N2 ~209 645 267 12.2 -1.2 -37.1 1,653 - 895 0.04129 0.3478 28.51 +155
. . .
Cotton(l)
Pyrocel- C6H7 ~5N2,4509 go 272 12.6 +0.7 -34.6 1.655 651800 941 0.04041 0.3454 28.11 183
lulose(2)
Blend(3) CH
6 7.365 N2.67010.27
281 13.15 3.4 -30.8 1.656 651700 1024 0.03920 0.3421 27.56 268.4

c6H7 ~3N2 6701034 28213.25 3.8 -30.2 1.656 650000 1034 0.03898 0.3415 27.46 279
Blend(3) . .
Guncotton(4) C6H7 . ~oNz . 7tOfo At 28413.35 4.3 -29.5 1.656 – 1040 0.03876 0.3409 27.36 291
Guncotton(4) C6H7 2GN2 ,401 ~ 46
. . 28513.45 4.8 -28.9 1.657 649000 1061 0,03854 ‘-).3403 27.26 305
Hi gh-Ni trq-
gen NC(5) C6H7N301 , 29714.14 8.1 -24.2 1.659 647000 1160 0.03704 0.3362 26.57 407
(l) Collodion cottons are also called “pyroxylins”. NC’s contg 11.0-11.2% N are used in manuf of
celfuloid, NC’s contg 11.5-.12.0% are used in manuf of some blasting expIs and NC contg 12,2k0.1~
N is used for military purposes. AH pyroxylins are SOI in ether-ethanol mixts and partially sol in
ethanol( 2) Pyrocellulose, or simply “pyre” used for military purposes, contains 12.6~o.1%N. It is
comp~eteiy sol in 2:1-ether-ethanoI (3) Blends are usualfy obtained by bIending “pyro” with
gun cotton, but they can also be prepd by direct nitration of cellulose with acids intermedi ate in
strength betw-those used in prepn of pyro and of guncotton (4)Guncotton used for-military
purposes contains 13.35- I 3.45% N. Its solubiiity in .2:l-ether-ethanol is 6 to 10% (5)1-Iigh nitrogen
NC can be prepd by nitration of cellulose with mixt of nitric-acetic acid with acetic anhydride. or
by other methods. It is sol in acetone, as are collodion cotton, bIend, pyro and guncotton (6)Heat
of Combustion, (-E), is taken from NBSJR 44, 387-93(1950) (7)Heat of Explosion, Q, is calcd from
the formula Q.(-E)-67421(,— 2C+0.5H-0) cal/g (8) Gas Vohtme, n, is calcd from the formula
Mol Wt
n= C+0,5H+0.5N (9)Mean Heat Capacity, Cv, is calcd from the formula CV=l.62C+3. 265 H+3.384N+ 5,1930
Mol Wt Mol Wt
( 10) Covolume, ~, , is calcd from the formtda qi =(). ~,@.2C+7.0H+17,0N+ ?,@ cm3/g; by mtdtiplying it
!
Mol Wt
by factor 27,7, the covolume is obtained in in3/lb (1 I) Relative Energy. in the Gas, E, is calcd
from the formula E.~E).132771~~
Mol Wt
 C 105

No 2( CP2), sol in eth-alc & contg ca 12%N. A industrial procedures described under
mixc of CP, & CP2, colloided with eth-alc$ was CELLULOSE NITRATES
used to make Poudre B(See B Poudre). Either Its properties are as foIlows: Ballistic
CP, or CP2 with NG was used to make Ballistite Potential, (Q: )gxVi/1000=789,
(qv); and both of them, with NG and non-volatile (Q~).xV./1000=766; Brisance by Sand Test,
SOIVS, were used to make Attenuated Ballistite Ii5~ ~an~ crushed vs 48g for TNT; Explosion
(See Vol I,p A506-L). Before WWII, Poridres SD Temperature, 170° dec(j see); Gas Volume
(saris dissolvants or solventess powders) were produced on explosion, detd(V) 743ml/g with
prepd in France. These pdrs consisted of NC H20 liq, detd(Vi) 917ml/g with Hz O gas, calcd
gelatinized with NG and without a vol SOIV. The (V= ) 904ml/g with H20 gas; Heat of Cornhstion,
so-called CP$D(which stands for NC contg (c$’) 2406cal/g at const press, (Q:) 2415cal/g
11.6-II .7%N, without solvent) was used in some at const vol; Heat of Explosion, detd (Q:)
of these proplnts. The designation CP3, 942cal/g with H20 gas, (Q:) 860cal/g with
sometimes found in Fr literature~ means NC with HZO gas at const vol, calcd t ~~c 849cal/g at
a N content to ca 11.5% (Refs 8,14,22 & 68) const vol; Heat of Formation, 615cal/g at
Italian collodion cotton and its specifica- const press;” Hydrolysis Test, 249 hrs, forms
tions are described by Molina(Ref 9), Mangini 1.22% HN09; Hygroscopicity, at 30° and 90% RH,
(Ref 60), Giua(Ref 62), Belgran&Ref 70) & ‘n gains ca 3%; impact Sensitivity, 2kg wt, PA App
Ref 69 3“ for 5mg sample vs 14” for TNT, Bur of Mines
According to P~rez Ara(Ref 51) & other App 8cm; Solub rlity, insol in w & eth, 99%.
sources V Spainish NC corresponding to Amer dissolves in eth-alc(2: 1), 63% dissolves in
Collodion Cotton (pyroxylin) is called COZOdZOn NeOH, 21% dissolves in ethyl nitroacetate, 11%
CP2 or A/god&n Colodiori and consists of a dissolves in ale; sol in acet, ethyl acetate,
mixt of octo- and nononitrocellulose. Its N methyl acetate$ propylene oxidel nitromethane,
is 11-127. and d 1/653; NO evolved was nitroethane & in other SOIVS; Stability by
lf@l$)@c/g of NC [See aIso Sancho(Ref 39)]’ 65.5°KI Test, minimum 35 reins and by 134.5°
Stettbacher(Ref 61) reported that the Heat Test minimum 30 reins; Vapor Pressure
compn & prepn of Swiss NC proplnts were at 60° 0.0 mrnHg; Volatility at (500 0.0% and
similar to Fr Poudre B. They differed only in Water Produced on Explosion 140g/kg of NC
form and size of grains. These proplnts were Uses. Pyrocellulose has been used since the
prepd by mixing in a “Knettmachine’ ‘(kneading Spanish-American War( 1898) in cannon and
machine)% and in the presence of eth-ale, 80 small arms proplnts. Historical development of
Guncotton(13-13.4%N) and 20% Collodion Cotton “P yr$? proplnts is described under Cannon
(11.7-1 2,2%N) to which was added 1-1,5% Propellants. The original US single-base
DPhA. The gelatinized mass was worked to the proplnts consisted of Pyrocellulose colloided
desired shape & size of grains, and the vol sol with ether-alc$ but beginning ca 19099 there was
evaporated by drying. These proplnts were added 0.5% DPhA to act as a stabilizer and
manufd by “Die Eidgenossische(Staatliche) this amt was later increased to 17.. This
Pulverfabrik in Wimms(Bern)(See Ref 27) period also saw the introduction of the
‘ ‘water-dry pr’ocess” which permitted manuf of
Pyrocellulose, Pyro or Pyrocotton [called proplnts in a fraction of the time reqd for the
Coton-poudre or CP in Fr(may be considered as C‘air-dry process’‘(Ref 44)
a mixt of Coton-poudre No 1 or CP, ( 13%N) and of Pyrocellulose propInts were unduly
Coton-poudre No 2 or’CP2(12%N); hygro and gave bright flashes when fired from a
Schiessbaumwolle in Ger; PirocolIodione in cannon. However, this compn remained std
Ital; Piroksilin No 2 or Pirokollodion in Russ; until adoption of FNH(fIashless-nonhy groscopic)
and P irocelulosa in Span] [Grade A NC, and NH(nonhygroscopic) single-has e proplnts ca
according to US Military Spec MIL-N-244A(2) 1. 1930. Yet, pyrocellulose proplnts were manufd
NC contg 12.6~0.15%N, which corresponds to & used extensively by the US Navy during WWII
“decanitrocellulose”, C24Hao01 ~(ON02)1 o, (Ref 75,p 248)
according to earlier nomenclature; mw 1098.56, To-day, in the manuf of NC propellants,
N 12.75%, OB to C02 -3’5%; wh solid d 1.655 there sometimes are used mixts of Pyrocellulose
Historical See under Cannon Propellants & Gwzcotton(qv)Y which are called Blend or
Pyrocellulose is made by the laboratory & Blended Nitrocellulose( qv). These mixts are
 C 106

designed tohave the desired solubility& Guncotton [called Coton-poudre in Fr(may be

viscosity characteristics, and a specified N considered as Coton-poudte No 1 or CP, nitrated
conrent(See also under Cannon Propellants) to higher than 13%N); Schiessbaumwolle or
Schiesswolle in Ger; I?ulmicotone in Ital;
Blend or Blended Nitrocellulose(Grade C NC, P iroksilin No 1 in Rus; Algod6n Fulminate or
according to US Military Spec MIL-N-244A). Fulmicot6n in Span; and Menyaku in J ap)(Grade
This NC prepd by blending 60-65% Gurzcotton B NC, according to US Military Spec MIL-N
(ca 13.4% N) with 40-35% Pyrocottorz(ca 12.6% -244A). NC contg 13.35% N minimum, which
N). The resulting ‘ ‘blend” contains corresponds to “endecanitrocellul ose”,
13015 ~0.05% N. Blended NC is used when it is C,4H2909(ON02)1 ,, according to earIier
desired to prep a single-base, smokeless proplnt nomenclature; mw 1143.56* N 13.47%; OB to
of high ballistic porential usirtg 2:] eth-ak as C02 -29%; wh solid, d 1.665; insol in eth-ale;
SOIV. It is not possible to prep this kind of sol in acet or in ethyl acetate
proplnt using straight guncotton because guncocton Guncotton is the military grade of NC
is only SI sol in 2:1 eth-al and therefore would contg the highest N content(ca 13.45%) possible
not form a colloid. The Blend is sol in 2:1 to obtain by nitrating cellulose with mixed
eth-alc to the extent of 35-407. or ca the nitric-sulfuric acids. The reason is not
percentage of PyroceIlulose in it. The resulting definitely known, but in 1901 Cross, Bevan &
colloid is quite suitable for the prepn of Jenks introduced the theory that cellulose
smokeless proplnts reacts partly, during nitration: with H2S04
Perparation of Blended NC is described forming sulfuric esters. These esters, being
under Guncotton(qv) very stable, prevent nitration beyond the
The props of the Blend are as follows: “endeca!” stage. If it is desired to prepare NC
Ballistic Potential, (Q~)gxVi/1000=845Y with higher than 13,4570 N, it is necessary to
(Q~)cxVc/1000=814; Brisance by Sand Test, use mixed acids which do not contain H2S04
48g sand crushed vs 48g for TNT; Explosion as an ingredient. Such acids can be:
Temperature, 200° dec(5 see); Gas Volume a)mixt of 99% HN03 + acetic acid + acetic
produced on explosion, detd(V) 720ml/g with anhydride
H20 liq, detd(Vi) 893ml/g with H20 gas, calcd b)mixt of 99% HN03 + phosphoric acid +
(Vc) 878ml/g with H20 gas; Heat of Combustion, phosphoric anhydride
(Q$) 2338cal/g at const press, (Q:) 2348cal/g at c )mixt of 99% HN03 + nitrogen dioxide(See
const vol; Heat O/ Explosion, detd (Q:) 1027cal/g Refs 23, 32)
with H20 liq, (~~ 946cal/g with H20 gas at d)mixt of 99% HNO~ + some anhyd salt readily
const Vol$ calcd ( d ~)c 927cal/g with H20 gas at absorbing water, such as Ca(NOa )2
const vol; Heat of Formation, 576cal/g at const e)N2 OS fumes obtd by distilling nitric acid
press; Hydrolysis Test, 240 hrs, forms 1.1% (Refs 23,25,28,41) and
HN03; Hygroscopicity, 30° and 90% RH, ca f)finally by renitrating Guncotton using either
2.5%; impact Sensitivity, 2 kg wt, PA App 3“ straight HN03 or HN03 combined with AcOH,
for 5mg vs 14” for TNT, But of Mines App 8cm; AC20 or an anhydrous salt
Volubility, insol in w & eth, S1 sol in ale, (See also under High Nitrogen Nitrocelluloses)
35-40% SO1 in 2:1 eth-ale, sol in acet, ethyl Preparation Of Guncottorz. Cellulose intended
acetate & in many other org SOIVS; Stability in for the prepn of Guncotton can be of cotton
65.5°KI Test, 35 min + , in 134.5° Heat Test, linters or wood pulp. Cotton linters are usually
30 minutes +; Vapor Pressure at 600, O.Omm Hg; received in 150-lb bales, while wood pulp
Viscosity in 5% acet soln at 25°, ca 1.4 sec cellulose is received in the form of sheets,
(for a steel ball 5/16” diam to fall a distance about 4ft wide, rolled into bales weighing ca
of 10”); Volatility at 60°, 0.0%; Water produced 700-lbs each. Before proceeding with nitration,
on explosion, 139g/kg NC cellulose must be pretreated
Uses. Blended NC is used in the manuf 1. Pretreatment of Cellulose. The bale of
of single-base and double-base proplnts. cotton Iinters is fed into a “balebreaker” and
Requirements of the US Armed Forces for NC’s then into a “cotton picker”. The fluffed cotton
used in manufg proplnts are given in is fed over a slow-moving, wire-mesh into a
Specification MIL-N-244A(See also Cannon drier equipped with steam heated coils & fans.
Propellant) The temp of drier is maintained betw 105-I 10°
 C 107

(220-230°F), and this operation reduces the follow(each preceded by a fresh water change)
moisture content of Iinters from 6-770 to ca 0.5%. for a total boiling time of 70hrs(See also Ref 16)
The Iinters are then removed from the bin, B. Pulping. Since cellulose fibers are not
weighed & transferred to the nitrating room solid but tubular? having capillary channels
In the case of wood pulp, the pulp sheets running thru them, part of the impurities present
are fed into a drier maintained at 110-115° in Guncotton are occluded in these channels
(230-240°F) by hot air jets. During a drying and cannot be removed unless the fibers are
time of ca 15 reins, the moisture content is cut into very short fragments. This operation
reduced from 4-5% to ca 0.5%. The dried Pu~P is done in an apparatus called a ~‘beater”,
sheets pass from the drier into a ‘<shredder” similar to that employed in the paper industry.
where they are reduced to peices about 5mm in The sction of the blades in the “beater” cuts
1ength the unpulped Guncotton to lengths of 1 mm or
If the cellulose is intended to be stored, less. Large amts of water, maintained alkaline
it should be kept in airtight containers due to by addn of Na2COa, are used during this
its hygro nature operation of pulping NC. The satisfactorily y
II. Nitration of Cellulose. The “DuPont pulped NC is transferred as a slurry to the
Mechanical Dipper Process” is now used ‘ ‘poaching” house
exclusively in the USAS A nitrating unit IV. Purification of Guncotton: A. Poaching.
consists of four stainless steel nitrators which Preliminary boiling of crude NC reduces its
discharge into the same centrifugal wringer. acidity while the pulping operation mechanically
Each nicrator is equipped with. two. vertica~ breaks down” the fibers into very small
. .
aglrators revolving m opposite dlrec~ions, fragments. However, these operations do not
imparting motion toward the center. These remove rhe acidity entirely and it is necessary
agitations consist of a series of vertical arms Y to subject the pulped NC to additional boiling
placed in such a manner, that when in motion in water. This operation is similat to that
the cotton(or wood pulp) is quickly drawn described under “Sour Boil” except that it is
beneath the surface of acid & away from the conducted in an alk medium(See also Ref 11).
fume exhaust line The water is boiled by injectining live steam
Typical compns of mixed acids, used in into the poachers and the operations of boiling
nitrating cellulose to Guncotton, are given & change of water are conducted as described
under CELLULOSE NITRATES, Preparation of under CELLULOSE NITRATES, Preparation of
NC(Industrial Manufactme of NC). The crude NC(Laboratoty Procedure) B. Washing.
Guncotton &~ spent acid are discharged from the Following poaching, the NC is sufficiently
nitratorinto a centrifugal wringer which removes washed with cofd water(not less than two
most of the acid. The spent acid is run into washings) under mechanical agitation, for
tanks where it can be used, after adjusting its ~hr intervals, to insure its compliance with
compn, for nitrating cellulose to Pyrocotton or US Spec ‘MIL-N-244A
where it is fortified to the same strength as the V. Screening, In order co obtain uniformity in
original MA for re-use. The wet Guncotton is proplnts & uniform ballistics in weapons, it is
immediately immersed in water to await necessa~ to have NC of uniform props(such as
{ ‘stabilization” & t ‘purification” N content, viscosity & etc). It is very difficult
III. Stabilization of Guncotton. A. Sour Boil. to achieve this uniformity among different batches
Due to the fact that acids & other impurities of NC. Good results are obtd when portions of
are strongly adsorbed on the fibers of NC and, batches having high N content & high viscosity
therefore, are hard to remove, the stabilization are blended with portions having low N content
of Guncotton is a tedious & elaborate process. & low viscosity. The resulting mixts possess
The preliminary or “sour boil” of crude Guncotton props intermediate betw those of the individual
is carried out in large wooden(cypress) tubs batches. This operation is done during screening.
equipped with ducts for heating & circulating The slurry from several poaching tubs is fed
water at a temp approx 100°. During the first thru a distributor arrangements which spreads
two hrs$ the acidity of the water is adjusted to the NC uniformly on a “Packer” screens. The
0.05 -O.50%(calcd as H2S04). After a boiling screen, having slots 0.02 inches$ is vibrated
treatment of not less than 40-hrs and a fresh mechanically and the properly pulped NC is
water change, then two separate 5-hr boils blended as it passes thru the screen into
 C 108

collecting boxes. If it is desired to obtn H20 liq, detd(Vi) 883ml/g with H20 gas;
Guncotton and not a Blended NC, the material Heat o{ Combustion, 2303cal/g at const vol;
goes from the screen directly to the wringers Heat o/ Explosion, detd (Q:) 1063cal/g with
to remove the remaining water H20 liq, (Q~)g 982cal/g with H20 gas;Heat
VI. Blending. From the standpoint of o/ Formation, 5S lcal/g at press; Hygroscopicity,
‘ ‘ballistic potential”, it would be advantageous 30° and 90% RH, ca 2%; Imbact Sensitivity,
to use straight Guncotton in smokeless 2 kg wt, PA App 3“ for 5mg samples vs 14° for
proplnts, but Guncotton is only S1 sol in eth-ale, TNT, Bur of Mines App, 9cm; Power by Ballistic
the mixt commonly used in the USA to colloid Mortar, 125% TNT; SoIubility, insol in w & eth,
NC. .Therefore, Blended NC(qv) which is sol in v S1 sol in ale, ca 10% sol in 2:1 eth-ale, sol in
2:1 eth-alc mixt to the extent of ca 40%, is acet, ethyl acetate & other org SOIVS; .$tability
preferred for single-base proplnts. In this in 100° Heat Test, loses 0,3% 1st 48 hrs and
operation 60-65% of Guncotton(13 .4%N) is 0.0% in 2nd 48 hrs, in 100° Vacuum Stability
blended with 40-35% of Pyrocellulose Test(5g sample) 1.5CC gas evolved; Vapor
(12.6% N). Each blending unit consists of two Pressure at 60°, 0.0 mm Hg; Volatility at
tubs, both equipped with propellor type 60°, 0,0%
agitations ~ interconnected in such a manner Uses. Guncotton is used for the prepn of
that the contents are kept in constant various flashless proplnts and in shrapnel shell
circulation. The receiving tub(or high tub) of a compns as a flame carrier. It is also used in
blending unit is filled with slurry from the electric primers & in eclectically initiated
screening operation so that the overflow destructors(Ref 55). When used alone it requires
discharges into the “low tub”. When the a SOIV such as acet; when used in “Blended
1atter tub becomes partly filIed, a circulating NC”, a 2:1 eth-alc SOIV may be used. The
pump is started and part of the slurry is requirements of the US Armed Forces for
returned from the “low” to the “high” tub. Guncotton used in military applications are
This operation continues for 6-7X hrs, after given in Specification MIL-N-244A
which time a sample is tested for N content High-Nitrogen Nitrocelluloses. This term
& volubility in 2:1 eth-alc. If satisfactory, the includes all NC’s having a N content higher
blended slurry is transferred to the “wringing than that of ordinary Guncotton, or from 13.75%
house” N to 14.14% N, the latter representing the
VII. Wringing. The transference of NC, from theoretical limit. Such a NC would consist
the ~ime of nitration thru stabilization purification principally of “dodecanitrate”,
& blending operations, is accompanied by large C24H2*O~(0N02)t z, according to earlier
amts of water which must be removed, since nomenclature; mw 1118.56, N 14.14%; OB to
water would interfere with the colliding of NC C02 -24%, d 1.67-1.70
by 2:1 eth-alc. This water from purified NC is In order to prepare a proplnt of higher
removed by wringing & partly by displacement ballistic potential than is possible with
with alc. The wringer is a centrifugal machine ordinary Guncotton, High-Nitrogen NC must be
with a perforated brass basket lined, with a used. It has already been explained under
24-mesh copper screen. The basket is geared to Guncotton that it is impossible to prepare a NC
revolve at 95o rpm Y which centrifugal action having higher than 13.45 % N by nitration of
forces the water from the NC to a drain. The cellulose with mixed HN03-H2S04 acids. For
time of wringing is ca 7 reins. The wrung NC this reason, High-Nitrogen NC must be prepd
(moisture content ca 31%) is discharged into by using other nitrating mixts, not contg
metallic, rustproof cans provided with tightly H2S04 as a dehydrating agent, Some products
fitting covers. This final operation concludes resulting from the u;e of these various nitrating
the manuf of NC mixts are as follows:
The properties of Guncotton(13 .45% N) are a)Nitration of wet Guncotton(25% H20) with a
as follows: Ballistic Potential, mixt of nitric acid + acetic acid + acetic
(Q:) xVi/100=867, Brisance by Sand Test, 49g anhydride(60:20:20 or 50:25 :25) and a ratio of
san # crushed vs 48g for TNT; Detonation Rate, guncotton to acid of 1 to 50, yields NC of 14%
7300m/sec at d 1.20g/cc; Explosion N, of low viscosity & suitable for military use;
Temperature, 230° dec(5 see); Gas Volume nitration of cellulose by similar nitrating agents
produced on explosion, detd(V) 712 ml/g with yields NC of 13.8% N(See Refs 17,18,20,21,35,
 C 109

47,56) prepn of high-ballistic potential smokeless

b)Nitration of celh,dose with a mixt of nitric proplnts, using a SOIV other than eth-alc. For
acid + phosphoric acid + phosphoric example, in a singIe-base proplnt contg 95
anhydride(49:49:2) and a ratio of cellulose to NC(14%N), 2.5 Ba(N03)2, 1.5 KN03, 0.75 DPhA &
acid of 1 to 50, yields NC of 13.8% N(Refs 2,10, ” O.25% graphite, a VOI SOIV of 70 acetone & 30%
12,29,30,31,34,36). The viscosity of this NC is alc may be used, or a mixt of acet & eth. In
very high, but it can be reduced & the NC prepg this proplnt, the water in wet NC is
stabilized by heating it in an 85/15 glycerin replaced in the usual manner by ale, and then
-water mixt or in an aq soln of Amm nitrate, or acet is added to make the total amt of SOIV
ammonia as proposed by several investigators equal to 50Z of the total wt of resulting proplnt.
c)Nitration of cellulose with 99% HN03 in the This SOIV mixt is removed by mild heating
presence of NH4N03 (15-20%) or KNOa(30%) In the prepn of a double-base proplnt
yields NC of 13.8% N(Refs 21,35). The salts contg 81.5 NC(14%N), 15.ONG, 1.5 Ba(N03)2,
prevent hardening & contraction of cotton linters 1.0 KN03, 0.75 DPhA & 0.25z graphite, the SOIV
which occurs when HN03 is used alone(Ref 21); can be the same as above, or it may contain
wet guncotton may be similarly nitrated more alc(43/47 acetone/alcohol). Due to the
d)Nitration of cellulose, in the shape of paper presence of NG, which acts as a gelatinzer
rolls, with NZ05 gas produced by heating coned for NC, the total amt of vol SOIV may be as
HN03, yields NC of 14% N. This process of low as 35% of the total wt of the mixt
prepg high-nitrogen NC was developed by the (See also Cannon Propellants, Propellants &
Germans during WWII(See Refs 23,25,2S,41) others)
The properties of 13.75% N NC are (This section was reviewed by Dr F. J. MasuelIi
intermediate between those of Guncotton(l 3.45%N) of PicAtsn)
& of 14% N NC R e~s on NC: l)Beil-not found 2)G.Lunge &
Following are the props of 14%N E.Weintraub, ZAngChem 12, 445(1899)(NC of
nitrocellulose: Ballistic Potential, (~7gxVi/1 000= 13.8-13.9% N prepd by nitration of cellulose
904, (Q~)cxVc /1000=867; Brisance by Sand Test, with HN03 & P205) 3)G.W.MacDonaId,
52g sand crushed vs 48g for TNT; Gas Volume ‘ ‘Historical Papers on Modern Explosives”,
produced on explosion, detd(V) 688ml/g with Whittaker & Co, London(1912) 4)Marsha11 1
H20 liq, detd(V~) 854ml/g with H20 gas, calcd (197), 135-93; 2(1917), 208,552 & 636 5)J.B.
(Vc ) 838ml/g with H20 gas; Heat of Combustion, Bernadou, “Smokeless Powder, Nitrocellulose
(~p) 2232cal/g at const press, (Q:) 2242cal/g at and Theory of the Cellulose Molecule”, Wiley,
const vol; Heat of Explosion, detd (Q:) 1137 . NY( 1917) 6)J .A.MarshallX “’The Manufacture
cal/g with HZO liq, (Q:) 1059 caI/g with and Testing of Military Explosives”, McGraw
H20 gas at const volt ca f cd (Q~)c 1051cal/g -Hill, NY(1919),pp 5-29 7)E.Worden,
with H20 gas at const vol; Heat of Formatiorz, “Technology of Cellulose Esters”, VanNoatrand,
516cal/g at const press; Hydrolysis Test, NY, Vol 1, Part 3(1921) 8)Pascal(1930),
240 hrs, forms 1% HN03; Hygroscojicity, 30° 99-135 9)Mo1ina( 1930), 206 9a)F .D.Miles &
and 90% RH~ ca 1%; impact Sensitivity, 2kg wt, J .Craik, JPhysChem 34, 2067 -20( 1930)(Theory
PA App 3“ for 5mg sample vs 14” for TNT, of nitration of NC) 10)E.Berl & G. Rueff, Ber
But of Mines App 8cm; Volubility, insol in w, 63, 3212(1930); Cellulosechem 12, 53(1931)&
eth, n-propyl alc & iso-propyl ale; 0.6 SOI in CA 25, 5760( i931)(NC with max of 14.04% N
ethanol? 1% sol in MeOH, 1.4% sol in 2: I eth-ale, obtd by nitration of cellulose with nitric &
20% SOI in methyl acetate, 42% sol in phosphoric acids) 1 l)F .Olsen, USP 1798270
nitromethane, 86% sol in l-nitropropane, and (1931) & USP 1893677(1933) 1 la) C. Trogus,
100% sol in acet, eth acetate, propylene oxide & Ber 64B, 405-7(1931) & CA 25, 5285(1931)
LUTLylacetate; Stability, in 900C vacuum (Nitration of cell with coned HN03-AcOH) 12)
Stability Test, 1.46cc gas evolved; in 100°Tesi, F. Lenze & E. Rubens, SS 26, 4(1931) & CA 25,
11+ cc in 24 hrs; Viscosity, 5% acet soln at 1674(1931); SS 27, 114, 154(1932) & CA 26,
25°, ca 2 sec(time reqd for a 5/16” diam steel 4473( 1932)( Prepn of high nitrogen NC, of 14% N,
ball to fall a distance of 10”); Volatility, by nitration of cellulose with HN03 & P20~)
at 600, O.O~; Water produced on explosiortv 13)G.de Bruin, SS 26, 84(193 l)(Without describing
133g/kg NC the method of prepn, deB claimed that he could
Uses. High-Nitrogen NC is used for the prep any NC between 2-14%N) 14)Vennin,
 Cll0

Butlot & Lfcorch6( 1932), 347-400 15) Marshall Dubien(Poudrerie National D’Angoul~me), MP
3(1932), 34-6, 142 & 208 16) H. Muraout, BullFr 28, 82(1938) & CA 33, 7570( 1939) (Nitration of
51, 1089-93(1932) & CA 27, 838(1933)(NC of cotton with HN03 & P20~ gave NC with a max
13.7% N was obtd by extracting the unstabilized of 13.8-13.9% N) 35)A.Bouchonnet et al, MP
Guncotton with inethanol or ethanol) 17) 28, 277, 295 & 308(1938) & CA 33> 8401(1939)
G.Darzens, MP 25, 437(1932-33) & CA 28, (Nitration of cellulose with 100% HN03 &
567 1(1934)(NC of 13.7% N was prepd by nitrating mineral salts, such as KN03 or NH4N03, gave
cellulose with 100% HN03 + acetic anhydride + chlf) NC of 13.8% N; nitration with HNO~+AcOH
18) L.Brissaud, Mp 25, 440-8(1932-33) & CA 28, +Ac20 50:25:25 gave NC of 14.1% N; and
567 1-2(1934) (NC of varying N content was prepd nitration with nitric acid vapors gave NC between
using nitrating medium similar to that of Darzens) 8.6 & 13.6% N) 36)E.Berl, BritP 470292(1938) &
19)Stettbacher( 1933), 122-46 20) K.Hess & C. CA 32, 779(1938)(High-nitrogen NC prepd by
Trogus, GerP 579285(1933)& CA 27, 4671(1933) nitration of cellulose with HN03+H3P04+P205 )
(Prepn of high-nitr~gen NC by nitration with 37)T.Ucbafkki & W. Szypolski, RoczChem 19,
H!N03+AcOH+Acz0) 21)A.Bouchonnet et al, CR 387(1939) & CA 34, 4566(1940)(Nitration of
197, 63-5(1933) & CA 27, 5979( 1933XA stabIe cellulose with HN03 & inorg salts Pave NC of
NC of max theoretical N content(14.14Z) was 13.3% N) 38)Thorpe 4(1940), 501-16 38a)M.
obtd by nitrating cotton linters with 50 HN03, Kassaroff, “Zur Kenntnis der Nitrozellulose”,
25 AcOH & 25% AC20); CR 197, 332-4(1933) & SS 35, 23, 49, 74 & 97(1940) 39)Sancho(1941),
CA 27, 5979-80( 1933)(A max of 13.8% N NC was 306-23 40)M.F06x, BullFr [5] 8, 381, 390
obtd with a nitrating acid of 99% HN03+ 15-20% [ 1941)&CA 36, 1491( 1942)(Prepn & props of NC
NH4N03 or 30% KN03) 22)Pepin Lehalieur of 13.7-13.8% N, prepd by nitrating cellulose
(1935), 221-46 23)Z.Rogovin & K. Tikhonov, with nitric acid vapors) 41)F.Trombe, BuHFr
Cellulosechem 16, 11(1935) & CA 29, 4169(1935) 9, 526(1942) & CA 37, 3942( 1943)(Nitration Of
(Nitration of ceIlulose with HN09 contg 5% cellulose with nitrogenous gases) 42)K.Fabel,
N20~, yielded NC of 13.7-13.8% N vs 13.3% N. NC 13, 83,123,164,207(1942); NC 14, 3-8(1943);
obtd with HN09 & 5% P205) 24)M.Mathieu, CR SS 38, 72,88,136(1943) & CA 38,1879, 2821(1944)
200, 401(1935) & CA 29, 2352( 1935)(Structure (A review of the props Of NC) 43)J .Barsha>
of trinitrocellulose) 25)R.Dalmon et al, CR ‘ ‘Inorganic Esters”, Chapter VIII B in Ott, vol
201, 664(1935) & CA 30, 283( 1936) (Nitration of 5(1943), 622ff 44)Davis(1943), 244-73 45)
ramie with N205 in chlf gave NC of 14.147. N; Bebie( 1943), 50 & 78 46)W.H.Rinkenbach*
stabilization reduced the N content to 13.88%); CIThermoChemistry of Nitrocelhdose”, PATR
CR 201, 1123-4(1935) & CA 30, 854(1936)(NC of 1265(1943) 47)H.Friese, Gerp 708237(1943) &
14. 12% N obtd by nitration of cellulose with CA 37, 2935( 1943 XNitration of wood or straw
N205 gas) 26) Z. Rogovin & S. Glazman, with HN03+AcOH+Ac20) 48)Hackh’s(1944),
ZhPriklKhim 8, 1237-47( 1935)( Physical 213 & 702 49)E.Heuser, “The Chemistry Of
heterogeniety of NC & props of its fractions) Cellulose”, Wiley, NY(1944), 172-222 50)R.S.
27)M.Mathieu, “La Nitration de la Cellulose. Jessup. et al, “Heats of Combustion of Cellulose
R~action Topochimique”, Hermann, paris( 1936), and Nitrocelluloses”, OSRD Rpt ‘3932(1944)
66pp 28)A.Bouchonnet et al, CR 202, 1437 (PB#22871) 50a)Kast-Metz(1944), 211 51)
(1936) & CA 30, 467 l(1936)(Nitrat ion of cellulose P~rez-Ara(1945), 358-98 52)1. Julander,
with fuming HN03) 29) A. Bouchonnet et al~ “Studies on Nitrocellulose”, Dissertation,
BullFr [5] 4, 560(1937) & CA 31, 5581-2(1937) Univ of Uppsala, Sweden(1945); ArkivKemi
(13. 5% N NC was prepd by nitrating cellulose Mineral Geol 21A, NO 8, l-145 (1945)(in Engl)
with HN03 92 and HPOa 8 ps) 30)A. Bouchonne\ 53)J .T.Matsh & F.C.Wood, “An Introduction to
Mp 27, 236(1937) & CA 31, 8200( 1937)(NC of the Chemistry of Cellulose”, Wiley, NY(1945),
14.05% N was obtd by nitration of cellulose 301-10 54)R.kLMcKee, USP 2377435(1945) &CA
with HN03 & P205) 31) T. Uraba~ski & Z. 39, 5487( 1945)(Nitration of cellulose in acids
Janiszewski, RoczChem 17, 349(1937) & CA of increasing strengths) 55)Anon, TM 9-1900
31, 8927( 1937)(Nitration of cellulose with NZ05 (1945), P 36 5@EJ31=rlY Usp 2384415(1945) &
gave NC of 14% N) 32) P. P. Shorygin & E.V. CA 40$ 206( 1946)(Continous nitrat ion us ~~g
KhaitY ZhObshchKhim 7, 188(1937) & CA 31, HN03+H3POa+P205) 57) J. Barsha,
4810( 1937)(Nitration of cellulose with HN03 & “Nitrocellulose”, in J .Alexander, “Colloid
N204) 33)Hayes(l 938), 17-26 34)Friederich & Chemistry”, Reinhold, NY, vol 6(1946), 860-86
 C 111

57a)Hercules Powder Co, “Nitrocellulose denigration of NC with mixed acids) 87)A.

-Properties and Uses”, Wilmington, Del(1947) Saposchnikoff(Sapozhnikov), SS 3, 201(1908)
58)Vivas, Feigenspan & Ladreda 2(1946), 113-48 (Influence of H2S04 on nitration of cellulose)
& 3(1948), 86 59)Dor<e( 1947), 233-50 60) 88)E.Berl & WSmith, Jr, JSCI 27, 534(1908) &
Mangini, Esplosivi(1947), 207-16 61)Stettbacher CA 2 2450( 1908)(AIkaline decompn of NC)
(1948), 41 & 62-6 62)Giua, Dizionario, vol 2 89)E.Berl & W.Srnith, Jr, Ber 41, 1837(1908) &
(1949), 132-9 63)Kirk & Othmer 3(1949), 361-70 CA 2, 2450(1908)(Prepn of 13.3$% N NC by action
64)E .K.Rideal & A.J .B.Robertson, “The of HN03+ acetic anhydride) 90)F. L. Nathan,
Spontaneous Ignition of Nitrocellulose”, paper JSCI 28, 177(1909)&CA 3, 1342( 1909)(A
presented at 3rd Symposium on Combustion, rdsumt$ of the history of NC manuf in England)
Williams & Wilkins, Bakimore(1949), 536-44 91)M.Schall, SS 12, 57(1917) & CA 12, 631(1918)
65) K. FabeI, “Nitrocellulose”, EnkeY Stuttgart (Recovery of spent acid in the manuf of NC & NG)
(1950) 66)R.S,Jessup & E. J. Prosen, “Heats of 92)B.J.Smart, ChemEngMinRev(Australia) 10,
Combustion of Cellulose and Nitrocellulose”, 380(1918) & CA 13, 262(1919)(Nitration of
JRNBS 44, 387-93(1950); NBS Res Paper RP marine fibers “Posidonia”) 93)G.de Bruiny
2086(1950) 67)A.P.Zakoshchikov, Rec 40, 632-64(1921); SS 17, 53, 58(1922) &
“Nitrotsellulosa”, Oborongiz, Moscow(1950) CA 16, 13 17(1922 )( Contribution to the study of
68)L.Brissaud, MP 33, 137-42(195 l)(Laboratory NC’s) 94)A.Logothetis & G. Gregoropoulos, SS
study of nitration of wood pulp) 69)Ital Army 17, 89(1922 )( Behavior of NC on heating under
Spec, MD Esercito, CapitoIato Tecnico Generale pressure) 95)E.C.Bingham & W.L.Hyden,
per la Fomitura di Esplosivi Propellenti(1951), JFrankInst 194, 731-40( 1922)(Study of fluidity of
CTF 29 to 33 70)Belgrano(1952), 98-109 71) NC solns) 96)R.G.Woodbridge, Jr, IEC 12,
Stettbacher, ~,61voras(1952), 86-90 72)A. 380(1922)( Manuf of NC from woodpulp) 97)C.K.
Kenneweg, “Uber den Umgang mit Nitroceliulose”, Krauz & F. J. Bletcha, C & EN 134, 1-4, 17-20
R. Miiller, Kdhn-Braunsfeld( 1952) 73)G.Champetier, (1927) & CA 21, 2795( 1927)(Prepn of 13% N NC
D~riv<s Cellulosiques”, Dunod, pari.s(1953) by nitration of cellulose with HN03 48.2 &
73a)F.J.Masuelli, “A Study of the Reaction of H3P04 50%) 98)I.G.Farbenind AG, FrP
Cellulose Nitrate with Various Reducing Agents”, 640087(1927) & CA 23, 1268( 1929)( Reduction
Doctoral thesis, Virginia Polytechnic Institute, of viscosity of NC by heating under pressure in w
Blacks burg, Va(June 1953) 74) J. Barsha at 140-70°) 99)E .Berl & E .Berkenfeld,
‘ ‘Inorganic Esters, Nitrocellulose”, in ott, VO1 ZAngChem 41, 130(1928) &CA 22, 3044(1928)
5, Part 2, 713-55 75)Anon, TM 9*191 O(1955), (Prepn of NC’s of various viscosities) 100)R.W.
127-35 & 248 76)F.D.Miles, “Cellulose Ryan & E. A.Lanz, IEC 20, 40-2(1928) & CA 22,
Nitrate”, lnterscience, NY(1955) 77)C.Bignotti, 1041( 1928)( Effect of temp on the rate of decompn
“Le Nitrocellulose”, Dr Carlo & Co, Firenze of NC) 10l)P.Demougin, Mp 23, 268(1928) &
(1956) 77a)Faith, Keyes & Clark(1957), 247-51 CA 24, 4387( 1930 XNitration of wood & other
(Manuf of NC) 78)Sax(1957), 946-7(Fite and cellulose) 102)M.G.Milliken, BrP 301267(1928)
expl hazards of NC’s) 79)PATR 1740, Rev 1 & CA 23, 407 l(1929)(Reduction of NC viscosity
(1958), 201-10 80)R.P .Antonelli, “Encyclo- by forcing w slurry of NC, under pressure, thru
pedia of Explosives”, OTIA, Durham, NC(1960), a special apparatus) 103)F ,D.Miles & M.
84-5 81)CondChemDict (1961), 293, 803 & 960 Milbourn, JPhChem 34, 2598(1930) & CA 25,
82)US Specifications MIL-N-244A(NC for use in 3163(1931)(Structure of ramie NC) 104)STARI
expls) and MIL-N-5538A(Tech NC for use in org (Service Technique de l’AffilIerie Royale
coatings) Italienne), Industria Chimica No’s 6, 7, 8 & 12
Additional Refs on NC: 83)A.Saposchnikoff (1930) and NO’S 1, 3 & 5(1931); French translation
(Sapozhnikov), SS 1, 453(1906)(Theory of in MAF 15t 481-557 (1936 )( Substitutes for cotton
nitration of celluIose) 84)A,Sapojnikoff in the manuf of NC) 105)J .Desmaroux & M.
(Sapozhnikov), MP 14, 42-64(1906-7)& SS 3, Mathieu, CR 192, 234(1931) & CA 25, 3163(1931)
444(1908 )(Decompn of NC at cemps below ignition (Structure of NC up to N content of” 13.9%) 106)
point) 85)E.Berl & R. Klaye, SS 2, 381(1907) & F,Lenz & E. Rube!ls, SS 26, 4(1931 )( Prepn of NC
CA 2, 184( 1908)( Researches on higher nitrates of max N content) 107)G.de Bruin, SS 26, 84
of ceIIuIose, hydrocellulose & oxyceiIuIose) (1931)(Study of NC of max N content) 107a)S.
86)E.Berl & R. Klaye, SS 2, 403(1907) & CA 2, Oguri & S. Terui, JSocChemInd(Japan) 34,
898(1908 )(Progressive nitration of cellulose & 422-6B(1931) & JSCI 51, BrA 140(1932)(Hygro of
NC) 108)H.A.Aaronson, pATR 208(1932) for NC & detn of rate of solution) 128)J,
(Relation between viscosity of cotton linters and Desmaroux et al, MP 29, 134-96(1939) & CA
of NC produced therefrom) 109)W.0.Snelling & 34, 1851 (1940)(Decompn of NC as a result of
R.N. Boyd, USP1873063(1932) &CA 26,6141 varied treatments) 129) H. A. Aaronson, PATR
(1932 )( Reduction of viscosity of NC achieved by 966( 1939)( Cellulose & NC produced from
heating it to 110° in an aq soln of NH4N03) bagasse pulp) 130)D.R.Cameron, PATR 1054
110)C.Krauz & A.Majrich, ChemObzor 7, 209-16 ( 1940)( Plant scale study of NC prepd from grade
(1932) & CA 27, 2812( 1933)( Effect of inorg & org A wood pulp) 131)H.C.Porter, IEC 32, 1034-6
salts on stability of NC)(See also Acidity in (1940) & CA 34, 6075( 1940)( Ignitability of NC &
Explosives, Vol l,p A90-R) lll)S.A.Glikman et various other materials in air) 132)K.Fabel, NC
al, Plastmassy(Russia) 11, NO 4, 11-12(1933) 11, 223-5( 1940)( Theory of cellulose nitration)
(Influence of Ca on the viscosity of NC) 112) 133)C.G.Dunkle, PATR 1100( 1941 )( Purification
C. J.Staud & J .T.Fuess, USp 1917400(1933) of NC from cotton linters) 134)G.L.Richter, OSRD
(Nitration of cellulose with N02 either in Rpt 71( 1941 )(Wood cellulose nitrates for
gaseous or liq state produces NC up to 12% N) munitions) 135)A.Kraus, NC 12, 63-4(1941) &
l13)P.Demougin, CR 196, 408-10 (1933 )( Volubility CA 36, 4748( 1942)( Volubility table of NC of
of NC as a function of pulping) l13a)H.A. various N contents in various solvents) 136)M.
Aaronson, pATR 408(1933)(Stabi1ity of wood Mathieu, CR 212, 80(1941) & CA 35, 6443(1941)
pulp for the prepn of Guncotton) 114)W. (X-ray photography of the process of nitration of
Scharrnbeck, SS 29, 33,67,98,133,196,230,266 cellulose by N20~) 137) K. Fabel, NC 12, 103,
(1934) & CA 29, 345(1935)(NC from wood 126(1941) & CA 37, 2928( 1943)( Review of
cellulose) l15)E.Rubens, NC 5,3,19,42,(1934) & nitration of cellulose from wood$ straw~ bagasse,
CA 28, 4593( 1934)(Use of domestic raw materials etc) 138)] .Desmaroux et al, CR 212, 212,396
in place of cotton for the production of NC) (1941) & CA 38, 1637( 1944)(Nitration of cellulose
116)M.Mathieu, BullFr 3, 346( 1936)( Nitration of in mixts of HN03 & O contg materials, such as
cellulose) 117)wASAG, GerP 634938(1936) & ether or dichlorodiethyl ether) 139)C.Kullgren,
CA 31, 339(1937 )( Nitration of cellulose in SvenskKemTid 53, 233-41(1941) & 56, 221-38
presence of wetting agents) 118)A.Foulon, SS ( 1944) (In Ger); CA 36., 262(1942) & 40, 2630
32, 348(1937 )(Description of Hercules method of ( 1946)(Stabilization of NC and comparison of
digesting NC as appeared in GerP 613063 of solubilities of NC prepd from wood pulp & from
1937) l19)M.G.Milliken, USp 2103592(1937) cotton) 140)H.A.Aaronson, PATR 1066(1941)
(Stabilization of NC by continous method) 120) (Nitration of high alpha cellulose wood pulp
E. Berl, BritP 469663(1937) & CA 32, 779(1938) from aspen wood by the Forest Products Lab
(Stabilization of NC by continous extraction at process) 141) J.M.Williams, OSRD Rpt 898
RT with MeOH or ethanol) 12 l) A. Bouchonnet & ( 1942)(Mechanism of gelatinization .& soln of NC
F.Trombe, BuHFr [5]- 5, 71 S(1938) & CA 32, in nonaqueous solvents) 142) L. Zapf, PATR
8769( 1938) (Apparatus for nitrating cellulose in 1159(1942)(Semi-plant scale purification of NC
dry HN03 vapors) 122)Deutsche Celluloid from cotton linters) 143)H.A.Aaronson, PATR
-Fabrik, GerP 643982(1938) & CA 33, 386(1939) 1187(1942)(Prepn & props of NC of high-nitrogen
(Military grade NC prepd by nitrating sulfite content) 144)R.W.Scharf, PATR 1190(1942)
wood @p) 123)M.F .Monbiot, BritP 495908 (Semi-plant scale purification of NC by ethanol)
(1938) & CA 33, 3152( 1939)(NC suitable for 145)R.O.Carter, Jr, et al, OSRD Rpt 1385(1943)
expls prepd by nitrating regenerated cellulose) (h4echanism of gelatinization & soln of fibrous
12~)S.A.Glikman, ZhFizKhim 1 I, No 4, 512-17 NC in non-aqueous solvents) 146)G.Petitpas,
( 1938)(Influence of electrolytes on viscosity of MSCE 30, 243-7(1943) & CA 40, 7614-15(1946)
NC) 125)T.Urba6ski et al, RoczChem 18, (Nitration of cellulose in mixts of HN03& O contg
856-64(1938) & 21, 120-3(1947); CA 33>4423 compds); MSCE 30$ 248-56(1943) & CA 40,
(1939) & 42, 4856( 1948)(UV & NC) 126)J . 7629( 1946)( Speed of nitration & gelatinization of
Meissner, GerP 670242 (1939 )( Continous method NC) 147)F .Vogel, PATR 1233(1943)(Semi
of nitrating cellulose) 127)A.Kraus, FarbenC hem -plant scale purification of NC from cotton
10, 236, 242, 301(1939); FarbenZtg 44, 1031, linters) 148)H,A.Aaronson, PATR 1331(1943)
1052(1939); NC 11, 226(1940); FarbenZtg 46, (Nitration of cellulose with N205 by the Stein
121, 190, 400(1941) & CA 34, 3109-10(1940); CA Hall Co process) 149)A.Stettbacher, protar 9,
35, 7800(1941); CA 36, 1174 -5(1942 )(Solvents 212-18, 233-42(1943) & CA 38, 4445(1944)
 C113

(Structure & some props of NC) 150)J.Ch6din & Giddens, IEC 39, 1303-9(1947) & CA 41,
A. Tribot, MSCE 31, 128-53(1944) & CA 40, 7110-1 l(1947)(StabiIization of NC with ammonia
761 3-14( 1946)(Rate of nitration of ceIlulose in and mechanism of the stabilization process)
different sulfonitric acid baths) 151)J.Ch6din, 174)L.Brissaud, MP 30, 205-9, 217-21(1948)
MSCE 31, 154-70(1944) & CA 40, 7614(1946) (Nitration of ceIIulose in mixts diluted with inert
(Mechanism of nitration of cellulose in relation to liquids; action of N~2 in nitrating acids on the
its structure) 152)G.L.Wilson & F. D. Miles, props of NC) 175)E .Calvet, MSCE 34, 179-93
TrFarad Soc 40, 150-63(1944) & CA 38, 5667 (1948 )(Nitration of cellulose) 176) J. Ch~din &
(1944)(Nitration of cellulose in vapor of HNO~) A. Tribot, MSCE 34, 277-87 (1948 )(Nitration of
153)H.A.Aaronson, PATR 1407(1944)(Use of cellulose) 177)H. Campbell & P. Johnson,
wetting agents in stabilization of NC) 154)G. JPolymerSci 3, 735-49( 1948),& CA 43, 8134
Schmid & E. Beuttenmiiller, ZElektrochem 50, (1949)( Interaction betwn NC in soln & inorg
209-1 5(1 944) & CA 40, 4590( 1946)(NC decompn) salts) 178)B.T.Fedoroff & W. R. Tomlinson,
155)R.L.Stern, USP 2366880(1945) & CA 39, Jr, “The Viscosity of High-Nitrogen
2404( 1945) (Purification of NC with particular Nitrocellulose”, Paper presented at the Army
attention to poaching) 156)W.E SiHick, USP -Navy Solid “Propellant Group, 111 Inst of
2367533(1945) & CA 39, 3159( 1945)( Recovery of Technology, Chicago, 111(19 April, 1948) 179)H.
waste HNOa in manuf of NC) 157)J .R. Yeager, Campbell & P .Johnson, JPolymerSci 4, 247-63
ChemMetEngrg 52, 113(May, 1945)( Milliken (1949) & CA 43, 8244( 1949)( Liquid & vapor phase
continous digester for NC) 158)] .Ch~din, MSCE adsorption of acetone by NC) 180) R. H. Blaker &
32, 108-34 (194~)(Mechanism of nitration of R.M.Badger, JPhCollChem 53, 794-803(1949) &
cellulose) 159)T.R.Olive, ChemEngrg 53, CA 43, 6888(1949); JACS 72, 3129-32(1950) & CA
92-6, 136-9(Dec 1946)(Ball powder process of 44, 8636( 1950)(Investigation of props of NC in
F .Olsen used by Western Cartridge Co at East soln by light-scattering methods) 181 )F.Trombe
Alton,III) 160)D.Fensom,CanJRes 24 E,83-7(1946) et aI, AnnChim(Paris) [ 12] 4, 745-810(1949) &
& CA 40, 4883( 1946)(Viscosities of NC gels in CA 44, 6119(1950)(Semi-pIant nitration of
80/20 mixts of NG/DEGDN) 161) F. Bouchard et celluIose to 13.8% N content by nitric acid
al, USP 2403493(1946) & CA 40, 6815(1946) vapors) 182)L.BrissaudY MP 31, 81-92, 145-60
(Manuf of NC) 162)H.Muraour & G.Aunis, MAF (1949) & CA 46, 11683(1952)(Nitration of
20, 4~3(1946)(Theromochemical props of NC) cellulose and dehydration of NC) 183)L.
163)H.vanKohorn, USP 2410319(1946)& CA 41, Rubenstein & B.Campbell, USP 2464777(1949)&
1104(1947)(Nitration of cellulose) 164)R.A. CA 43, 6228( 1949)(Addn of 4-12% NC, having a
Cooley, ChemInd 59, 645(1946) & CA 41, 863 fiber length 30-35 microns, to LA in detonators
( 1947XManuf of NC in Japan by continous reduces sensitivity & improves Ioading
method) 165)S.Watanabe, JSocTextileCeNulose characteristics) 184)P. Walter, Farben, Lacke,
Ind(Japan) 1, 636-41(1945) & CA 44, 6117(1950) Anstrichstoffe 3, 252-9(1949) & CA 43, 8681
(Nitration of cellulose with a chloroform-acid (1949)(Collodion cotton; a review) 185)B.T.
system) 166)J.Ch4din & A. Tribot, M.$CE 33, Fedoroff, PATR 1717(1949)(Prepn of low
143-57( 1947)(Mechanism of nitration of cellulose) viscosity, high-nitrogen NC) 186)P .Forest &
167)G.J.Doyle et al, JPhysCoHChem 51, 569-79 Y .Lacroix, MP 32, 33-40( 1950)(Stabilization of
(1947 XViscosity of NC) 168)J.Taylor & C.R.L. NC in an autoclave) 187)N.Moreau & Y. Lacroix,
Hall, JPhCollChem 51, 606-10(1947) MP 32, 443-62 (1950 )(Prepn of low viscosity NC
(Thermodynamic consts for NC of 12.16, 12.73, by treatment with ammonia) 188)] .F.von
13.10, & 13.24% N contents) 169)M.O.Schut & Gizycki, ChemZtg 74, 649-51 & 662-4(1950); CA
D. H.McMurtie, CanP 443769(1947) & CA 41, 45, 2209 & 4443(195 i)(Thermal degradation of
7120(1947)(Nitration of wood pulp to NC of 13% N) NC by prolonged heating at 100°; hydrolytic
170)G.J.Doyle et al, JPhCollChem 51, 569-74 decompn of NC during boiIing in water) 189)].
(1947) & CA 41, 4023( 1947 XViscosity of NC) Cummings et al, JSocMotPictTelevEngrs 54,
171)R.H.Blaker et al, JPhysCollChem 51, 574-9 268-74(1950) & CA 44, 4809( 1950)(Spontaneous
(1947) & CA 41, 4023( 1947)(Molecular ignition of decompg NC- film) 190)L.P.Kuhn,
heterogeneity of NC) 172)W.R.Ashford et al, AnalChem 22, 276-83( 1950)(IR spectra of NC)
CanJRes 25B, 151(1947)& CA 41, 4311-12 191)A,R.BoyIe & F. J. LIewellyn, JSCI 69, 179-81
( 1947)(Effect of alkalies on NC & on other (1950) & CA 44, 11097(1950)(Electrostatic
nitrated carbohydrates) 173) R. E. Reeves & J ,E. ignitability of puIped NC & some Cordites)
 C 114

192)B.G.Ranby & H.Sihtola, SvenskKemTid 62, kinetics & mechanism of nitration, denigration &
229-39(1950) & CA 45, 6379( 1951)(Study of decompn of NC) 210) J. Fauveau & L. Brissaudy
heating NC in an autoclave in acidified water Frp 1002689(1953),” described in Mp 35., 331
at 120°) 192a)S.Nernoto, JapP 181448(1950) & (1953)( Improvement in method of prepg
CA 46, 1256( 1952)(App for continous nitration of industrial NC intended for use in varnishes,
cellulose) 193)W.Dardel, InstS ewagep~ify J and paints, films & celIuloid) 211 )InstNacional de
Proc(Berne, Switz)l 950, 174-200 & CA 46, 6299 Industria & A.Garcia, SpanP 210044(1953) & CA
( 1952)(Description of tyPicaI Swiss 49, 3538( 1955 XStabilization of deteriorated NC)
sewage-purification plants, among the? purification 212)R.L.Trask, PATR 1961( 1953)( Summaty rept
of wastes from the manuf of NC) 194) E. Calvet & of lab studies to characterize sulfate wood pulp
J.Dhers-Pession, MSCE 35, 45-51(1951)& CA for NC) 213)G.Ch4rubin, BullFr 1954, 192-5 &
46, 490 l(1952)(Heat of esterification of cellulose CA 48, 9684( 1954)(Nitration of cotton Iinters)
by HNOa) 195)L.Nicolas, BullAssocTechInd 214)H.Maisner, USp 2690964(1954) & CA 49,
Papeti;re 5, 427-35(1951) & CA 46, 3758(1952) 618(1955 )(Expl gels, consisting of NC & liq
(Influence of method of nitrating cellulose on nitroparaffins, used as sensitizers in expl compns)
degree of polymerization of NC) 196)J .Ch~din & 215 P. Jowdin & R. Tribot, MP 36, 65-70(1954)&
A.Tribot, Ibid 5, 435-43(1951) & CA 46, 3757 CA 50, 2173( 1956)( Action of alkalies on the
(1952); MSCE 36, 31-42( 1951)(Different techniques stability of expl grade NC) 216)M.Parpaillon,
of nitrating cellulose fibers) 197)M.S.Schechter, MP 36, 177-87(1954) & CA 50, 2173(1956)
C & EN 29, 1150(1951) & CA 46, 3279(1952) (Reaction of DphA with NC & with other nitrate
(Acetone-moist NC dried in an elec oven at esters in the presence of acetic acid) 217)G.
110° exploded after Z hr; the material had not Matsumoto, J apP 7495(1954) & CA 50, 4510
been previously dried in air) 198)D.Montenegro, (1956 )(APP for continous nitration of cellulose)
Engenharia e Qu(m(Brazil) 3, 197-8(1951) & CA 218)T.H.Smith, NorskSkogindustri 8, 402-8(1954)
46, 10613(1952); Actas y Trabajos CongrSudamer (in English) & CA 50, 17431 (1956) (Fractionation
Qu~m 5° Congr(Lima, Peru) 1, 391-5(1951) &CA of NC according to degree of substitution) 219)
49, 15241( 1955)(Stability of NC improved by R. M. Brooks, USP 2678310(1954)(Two-stage
heating with aq DPhA) 199) L. Brissaud, Mp nitration of cellulose with straight HN03 to NC
33, 137-42(195 1 )(Suitability of wood pulp for contg 12.01 to 13.41% N) 220)V.I,Alekseenko et
nitration to NC) 200) Y. Matsumato, JapP al, DoklAkadN 95, No 1, 93-6( 1954) (Compatibility
676(1951) & CA 46, l1682(1952)(Prepn of NC) of NC with other high polymers) 221)Serrano de
201)H.Henkins & R.McGill, IEC 44, 1393(1952) Pablo, Revista de Aeronautic 4, 41(1954)( Prepn
(Expln temp of 13.4% N NC was 242° in 4 sees of NC from cotton$ straw & rags; expl problems
and of 12.6% N NC 243° at 4.2 sees; no expIn in Spain) 222)E .Grison & J .Quinchon, MP 37,
for both at 170°) 202)L.Brissaud, MP 34, 59-84(1955) & CA 50, 17452( 1956)( The beating of
341-50( 1952) (Prepn of granulated NC) 203)J. NC; comparison of different types of beaters)
Fauveau, Chim & Ind(Paris) 67, 304-5(1952) 223)S.Ronssin, MP 37, 85-96( 1955) (Measurement
(NC in the form of spherical grains) 204)Y. of specific surface of NC) 224)S. Wantannabe,
Kate, JapP 2292(1952) & CA 47, 6658(1953) JChemSocJapan, IndChemSect 58, 625-7(1955) &
(Reduction in viscosity of NC by treating it in CA 50, 7449( 1956 XActivation energy of decompn
an autoclave with cold water or air) 295)L. of NC & “bursting point” of NC) 225}W.A.
Nicolas, MSCE 37, 275-85(1952) & CA 48, 9684 Caldwell, JOilChemists’ ASSOC 38, 431-54(1955)
( 1954)( Influence of method of nitration on degree & CA 50, 11662(1956)(Industrial manuf of NC)
of polymerization of NC; intrinsic viscosities of 226)L.V.Rozental & E .K.Podgoretskii, ZhKhim.
NC in various solvents) 206)K.Thinius & P, Prom 1955, 112 & CA 50, 11662(1956)(Inf luence
Runze, ChemTech 4, 295(1952) & CA 48, 7317 of surface-active agents on dehydration of NC)
(1954)( Flammability of NC films) 207)L.Brissaucij 227)0. Riiber, NorsltSkogindustri 9, 204-7(1955)
MP 34, 341-50(1952)& CA 49, 2735( 1955)(NC (in English) & CA 50, 17431(1956)(Influence of
granules; a type of ball powder) 208)J.J. nitrogen content on the intrinsic viscosity of NC)
Creasey, Paper-Maker(London) 125, 398-400, 228)C.F.Bennett & T.E.Timell, Svensk-
402-4(1953) & CA 47, 7792( 1953)( Expln & fire Papperstidn 58, 281-6(1955) & CA 50, 2973(1956)
hazards of NC films) 209)R.W.VanDohah, “The (Prepn of 14.14% N NC) 229)M.L.Wolfrom et al,
Chemical Properties of Nitrocellulose”, Allegany JACS 77, 6573(1955); 78, 4695(1956); 80, 946&
Ballistics Lab Rpt(Jan, 1953)( Structure of NC; 1675(1958); 81, 1221 & 3469( 1959) (Controlled

-.-— —.—
 C115

thermal decompn of NC) 230)J?.Lhoste & 0. pulp) 250)Y.Lacroix & N. Bugat, MP 41, 39-47
Naud, MP 38, 137-43(1956)(The level of ( 1959)(Detn of NC losses during cooking in an
nitration of industrial NC’s) 231)L.Brissaud autoclave) 25 l) C. Fr~jacques, FrP 1189916
et al, MP 38$ 145-57( 1956)( The beating of NC; (1959) & MP 42, 477-81 (196@(Improvements in
comparison of Horn & Thorsen beaters and the nitration of celIulose) 252) L. Brissaud et al?
measurement of specific surface of NC) 232)Y. FrP 1200864(1959) & MP 42* 501-7(1959~
Lacroix et al, MP 38, 159-66( 1956)( The beating (Improvements in nitration of cellulose) 253)
of Guncotton) 233) K. Brimley, BritP 787411(1956) M.Giua et al, “Trattato di Chimica Industrial”,
& CA 58, 7704( 1958)(Plasticized NC of high N UTET, Torino 6(1959), 170-213 254)P .
content & low viscosity for prepn of plastic Lhoste & J. P.Dubois, MP 42, 29-37(1960) &
incendiary mixts) 234)K.T.Carolan & M. Chmura, CA 55, 17t)05(1961)(Special props of sulfuric
PATR 2440( 1957XStorage stability of NC ester impurity in NC’s) ‘“255)P .Lhoste & O.
plastics) 235)J.S.Musgrave & R. L. Trask, PATR Naud, MP 42, 205-22(1960)& CA 55, 17006
2444( 1957)(Effect of NC stabilization CYCle On ( 1960 XAction of NG on NC) 256) M.A.Millett
cycIe on stable life of proplnts) 236)M.A1 et al, Forest Products Lab Final Rpt”,
Millett,’ ‘Studies on the Thermal Decomposition Fundamental Studies on the Characterization
of Cellulose Nitrate and Cellulose Nitrate of Nitrating Pulps-Stability Studies of
Propellants,” Forest Products Lab, Madison, Cellulose Nitrate”, (1960) 257)ICI, Ltd,
Wisconsin(l 957)(A literat~e survey from CA Nobel Division, ‘ ‘Industrial Nitrocellulose”,
1907-56) 237)M.A.Millett, “Stability Tests for Kynoch Press, Birmingham(1961)
Military Cellulose Nitrate and Cellulose Nitrate
Propellants”, FPL(1957)(A literature s~vey CelIulose Nitrate, Action of So!vents(Swelling,
1907-57) 238)M.A.Millett et al, ‘{The Kinetics Gelatinization, Volubility and Plasticization).
of Rapid High Temperature Stabilization of As a general rule solvents for polymers like NC
Cellulose Nitrate”, FpL FinaI Tech Rpt(1957) act at first as swelling agents and only after-
239) J. Bonnet, Chim & Ind(Paris) 77> NO 1, wards as dispersing reactants. NC is capable
100-2(1957)(Study of nitration of cotton, of forming “swelling compounds” with a
emphasizing diffusion & swelling phenomena number of org solvents(such as cyclohexanone,
which are main factors in the rate of nitration) fenchone, m-xylene, etc) without losing its
240) G. Molinet, Mp 39, 21 5-25( 1957)(Stabi1ity Of fibrous structure~- Solubiliry of polymers like
NC) 241)Y.Lacroix & J.Mars, MP 30, 227-37 NC is not as clearly defined a property as that of
( 1957)(Aucomatic Taliani app for measuring low mol wt compds. When NC is treated with a
stability of NC) 242)W.A.Schmelling, BOW solvent a “gel” is obtained and the phenomena
(Baraboo, Wisconsin), TechRept 165(1957) is known as “gelatinization”. If the solvent is
(Lab investigation of multiphase nitration of volatile, it can be evaporated in order to obtain
cellulose) 243)P .Lhoste, MP 40, 77-81(1958) & a plastic-like colloided material. A smokeless
CA 55, 3055( 1961)(Su1fWic acid imP~ity in NC(or NC-NG) proplnt processed with the aid of
cellulose trinitrate prepd by mixed acids) .244) an ether-alcohol mixt is an example. If the
P. Lhoste & O.Naud, MP 40, 83-92(1958) & CA solvent is noh-voIatile, or only slightly
55, 3053( 1961) (Stability of cellulose trinitrate volatile, the NC forms a gel, but usually heat is
& relation between its ion exchange power and required for completion of operation, A double
the Abel test) 245 X3.Ronssin, MP 40v 457-71 -base(NC-NG) solventless smokeless proplnt is an
(1958) & CA 54, 25825( 1960)(Measmement of example. If heating is undesirable(because of
specific surface of NC’s, powders, fibers and danger) gelatinization can be achieved by
of crystaIs) 246) R. L. Trask, P ATR 24~.f( 1?5:;) blending NC at RT, with gelatinize dissolved or
(Pilot-plant studies of sulfate wood pulp as a suspended in a liq(such as alcohol) which is not
source of military NC) 247)E. Kaila, Paperi ja necessarily a solvent for NC. If a solid
Puu(Helsinki) 40, 339(1958)& CA 52,19121 gelatinize, such as camphor, is used(as in the
(1958)(NC dissolved in butyI=ine or other org prepn of Celluloid), the water-wet NC is mixed
amines for use in expls) 2.48)D.Gross & A.F. with powdered camphor, some alcohol is added
Robertson, JRNBS 61,413’ 1958) & CA 53,8629 and the mass is kneaded at RT for several hours.
( 1959)(Self ignition temps of materials, such aS The .process is usually called “plasticizacion”
cotton linters -& NC plastics) 249) L. Brissaud & P. It is not very easy to distinguish between
Miaud, MP 41, 27-38( 1959)( Nitration of wood “gelatinization” and “plasticization”. Both
 CI16

phenomena give similar plastic-like materials, various agents in gelatinization of NC)

which are flexible and crack-resistant. Accdg to 10) J.Desmaroux & M.Mathieu, CR 191, 786-8
G. Rugger of PicArsn , a “gelatinizer” tends to (1930) & CA 25, 2900(1931)(X-ray study of
draw the molecules together, whereas a gelatinization of NC with NG, cyclohexanone &
C‘plasticizer” spreads them acetophenone) 11 )J .Desmaroux, Mp 24, 211-33
The volubility of NC in org solvents and ( 1930 -1931 )(Study of gelatinization of NC with
formation of “gels ‘‘ is attributed to formation of nitroglycol) 12)J .Desmaroux, JChimPhys 1931,
molecular addition compds betw NC and the 163-73 & CA 25, 4170( 1931)(Affinity of NC for
solvent. Numerous papers were published on gelatinizers; a review) 13) A. J. Phillips,
this subject and the most important of them ate PATR 279( 1932)( Study of efficiency of various
listed below, including their titles or short agents in gelatinization of NC) 14)(? )Thomas,
abstracts MP 25, 115-20(1932-1933) & CA 27, 4083(1933)
From the practical point of view, it is [Detn of “coefficient of swelling’’ (coefficient de
important to know that soly of NC in a solvent is gonflement” in Fr) in water, ether & eth-alc
a function of its N content and to a lesser extent mixts. This coefficient is defined as ‘ ‘the
of its viscosity. No categorical statement can be apparent increase in vol in cc per g of NC as
made regarding the soly in any class of solvents. measured after contact for 24hrs betw liquid &
Other factors, such as temp, time, method of NC”. For its detn, a sample of dry, pulped NC is
manuf, presence of impurities, etc, might also placed in a graduated test tube of 12.4mm ID
influence the SOIY but to a lesser extent(see and the height is measured. Then the liq is
also Refs 32, 34, 64, 69 & 74) introduced, the tube stoppered & shaken,
(This section was reviewed by Dr F. J. MasuelIi allowed to stand for 24hrs and the new height of
of PicArsn) NC is measured] 15)L.M4dard, MP 25, 449-54
Re/s: l)M.Marqueyrol & D. Florentin, MP 18, (1932-1933) & CA 28, 5650( 1934)(Relation betw
150-67(1921) & CA 16, 2990( 1922) (Various electrical moment and gelatinizing power of NC)
gelatinizes for NCJ 2)J .Desmaroux, MP 18, 16) P. Demougin, MP 26, 37-41( 1934 -5)( Relation
168-82(1921) & CA 16, 2990( 1922)( Gelatinization betw soly of NC and its N content) 17)M.
of NC and “coefficient of gelatinization) 3)Ab Mathieu, CR 199, 55-7(1934) & CA 28, 5659
der Halden, MP 18, 183-4(1921)& CA 16, 2991 ( 1934)(X-ray examination of gelatinization of N
(1922) [Modification of detn of “coefficient of with acetone. It is compIete when I moI of acet
gelatinization” of NC fitst described by has been fixed by each N03 group of NC and
Desmaroux. Procedure: Introduce into a large this is shown by the disappearance of any
test tube, provided with a stopper, a sample of tryst structure) 18)J .Desmaroux, CR 199,
NC(() .5g)(previously dried in an oven & cooled) 148-50(1934) & CA 28, 5659( 1934~Gelatinization
and add 25ml of 2: l-ether-amyl alcohol mixt. of NC with acetone) 19)M.Mathieu, “La
Stopper the tube and keep it, with frequent G~latinisation des Nitrocelluloses”, Hermann &
shaking, in a water-thermostat at 20° for 18hrs. Cie, Paris(1936) 20) P. Parodl-Delfino, USP
After centrifuging, decant 5ml of the clear 209645 1(1937) & CA 32, 357(1938 )( Gelatinization
liquid, evaporate the solvent and weigh the of NC with NG in the presence of the triacetate
residue, Calculate the coefficient from the of an alkyl, such as of methyl-trimethylol
formula(Wt of residue)x 100/Wt of sample] 4)J. methane) 21) J. T. Power & K. R. Brown~ USP
.Desmaroux, MP 23, 54-62 (1928 )( Study of 2102187(1937) & CA 32, 1455( 1938) (Gelatinization
gelatinization of NC with camphor) 5)A.J. of NC with NG may be accelerated by a small
Phillips, JPhysChem 33, 118-30(1929)(Behavior amt of ethoxyethyl nitrate or acetate) 22)W.A.
of NC in polarized light) 6)J .J .Trillat, CR Sisson, [EC 30, 530-37(1938)(X-ray diffraction
191, 654-6(1930)& CA 25, 1377(1931) behavior of cellulose derivs) 23) J. T. Power &
(Gelatinization of NC with camphor; detn of K.R.Brown, USP 2106188(1938) & CA 32, 27S4
structure of celluloid) 7)J .C.Derksen et al, (1938); Britp 498346(1939) &CA 33, 4788(1939)
ZPhysChem 149A, 371-81(1930)& CA 24, (Gelatinization of NC with NG is accelerated by
5201( 1930)(Gelatinization of NC with camphor) the use of ca 1% of an alkyl ether of hexahydric
8)J .R.Katz et al, Ibid 151-A, 145, 163 & 172 alcohol, contg at least 5 ether groups, such as
(1930); CA 25, 2623(193 I)(Gelatinization of NC penta-methyl- or penta-methyl- mannite or sorbite)
with camphor; structure of celluloid) 9)A, J. 24) L. P. Kyrides, USP 2126560(1938) & CA 32,
Phillips, PATR 72( 1931) (Study of efficiency of 7926( 1938)( Cyclohexylamine as gelatinize for

— . . ..
 C 117

NC) 25)J.Desmaroux, MP 28, 204-35(1938)& CA 38)k. Calvet, CR217, 482-3(1943)&CA 39,

33, 8469( 1939)(Absorption of cyclopentanone by 2690( 1945 XCalorimetric study of gelatinization of
NC) 26) J. D. Hopper, PATR 952(1939)(Study new NC with acetic esters) 39)A,J.Phillips, PATR’s
solvents as possible ingredients of proplnts) 1249(1943) & l!587(1946)(Re1ation of hydrogen
27)AIvaro-AIberto, AnnAcadBrasilSci 11, 19-20 -bonding concept to gelatinization of NC 40)T.
(1939) & CA 33, 5659(1939) [Confirmation of Petitpas, MSCE 30, 201-42(1943) & 41 i 2573
theory of M.Mathieu(See Refs 17 & 19) in case of ( 1947XThermodynamic & structural studies of
complete gelatinization of NC with acetone] 28) the absorption of various gelatinizes by NC)
L.M6dard, MP 29, 10-11(1939) & CA 34, 1468 41)A.Soler, Ion(Madrid) 4, 455-63 & 480(1944) &
( 1940)(Study of gelatinization of NC with various CA 39, 1055( 1945)(Study of gelatinization of NC
mineral acid esters: MeSP06 & Me2SOa of 11.8% N. with NG in the presence of EtCentr at
gelatinize all NC’s rapidly and completely; various stages of the rolIing process) 42)A.
Me2S04 & 80/20-EtNOa/EtOH gelatinize Soler, AnalesFfs y Qu[m(Madtid) 40, 266-80(1944)
collodion- and pyrocotton and onIy incompletely & CA 42, 8048(1948) [Study of the effect of temp
guncotton; Mea B03, PrNOz, BuN02 & PrN03 on “coefficient of gelatinization of Soler’’(See
have no gelatinizing action on NC) 28a)A,R. Ref 37), showed that, generally, it increases with
Nees, IEC, AnalEd 11, 142( 1939)(Detn of color the temp] 43)Kast-Metz(1944), 201-4( Gelatinization
and turbidity of solns) 29) J. T. Power & K.R. ability of NC) 44)~.Calvet, MSCE 32, 168-99
Brown, USP 2146026(1939) & CA 33, 3590(1939) (1945 )(Study of mechanism of gelatinization of NC
(Gelatinization of expls, contg NC, with NG is by employing the microcalorimeter method) 45)
accelerated by the alkyl ester of an anhydric alc fi.Calvet & J, Coutelle, MSCE 32, 200-19(1945) &
contg at least one free OH group and having CA 42, 8581 -2(1948 )( Calorimetric study of
alkyl group contg not more than 5 carbon atoms~ gelatinization of NC with methyl nitrate acetic
such as methylanhydtosorbitol and dimethyl- esters and ether-alcohoI mixts ) 46)T.Petitpas &
anhydrosorbitol) .30)H.Fassnacht, USP 2194544 M.Mathieu, TrFaradSoc 42B, 17-33(1946)
( 1940) & CA 34, 4908(1940) [Gelatinization of NC (Reactions occuring in the gelatinization of
with a liq expl ester(such as NG) is -accelerated NC’s) 47)fi.Calvet & G.S6bille, CR 222,
by adding an aliphatic monohydric alc contg a 84-5(1946) & CA 40, 4284( 1946) (Calorimetric
carbonyl group, such as diacetone ] 31)T. study of gelatinization of NC with ether-aIcohoI
Petitpas, JChimPhys 37, 6-18(1940) & CA 34, mixts) 48)P.F.Macy, PATR 1616(1946)
6064( 1940)(Study of gelatinization of NC with (Development of explosive plasticizers for NC)
acetone, cyclopentanone and hydrocarbons) 32) 49)B .T.Fedoroff, PATR 1619( 1946)(Development
A. Kraus, NC 11, 226-7( 1940) (Action of liquids on of non-explosive plasticizers for NC) 50)P.F.
NC of various N contents; a table of solubilities Macy, PATR 1638(1947)(Explosive plasticizers
of NC’S) 33)M.Wadano, Kolloid-Z 92, 324-38 for NC) 51)T.Petitpas, Chim & Ind(Paris) 58,
(1940) & CA 35, 2634( 1941)(Relationship betw N 17-53(1947) & CA 42, 757( 1948)(Review of work
content of NC a.ld its SUIY) 34)A.~aus $ NC done, mostly in France since 1923 on gelatiniza-
12, 63-4(1 941)(Soly of NC’s of various N content tion of NC) 52)J .Ch;din & R. Vandoni, MSCE
and viscosities in various solvents; a table) 35) 33, 205-18(1947) &CA 43, 4927-8(1949)
fi. Calvet et al, CR 212, 542-4(1941); 213, 126-8 (Discussion on gelatinization of NC with
(1941) & 214, 716-18(1942); CA 36, 6073(1941)& acetone & with other substances) 53)T,Petitpas
38$ 3888( 1944 XCalorimetric study of gelatinization & M. Mathieu, MSCE 33, 219-37( 1947) (Study of
of NC with acetone) 36)N,Ipartelepek$ HungP reactions of gelatinization of NC’s) 54)B.T.
128457(1942) & CA 42, 9180( 1946)( Gelatinization Fedoroff, PATR 1678(1948XPrepn of high N,
of NC suspended in hot W) 36a)A. J. Phillips, low viscosity NC and the search for efficient
PATR 1201 (1942 )(Study of gelatinizing action of non-expl gelatinizes) J5)D. Fenson, CanJRes
esters of phthalic and adipic acids on NC) 37) 26B, 59-69(1948)& CA 42, 4347(1948)
ASoIer & A.Vain, Ion(Madrid) 2, 745-52(1942)& (Photoelectric study of rate of gelatinization of
CA 37, 2572(1943) [ Detn of gelatinization of NC NC with NG) 56)S.Axelrod, PATR 1681(1948)
with substances usually employed as stabilizers (Gelatinization of NC with liq expls, such as
(such as EtCentr, Ph-urethane, etc), expressed nitromethane) 57)B.T.Fedoroff, PATR 1753
as the “coefficient of gelatinization of Soler”. ( 1949)(Non-expl plasticizer for NC) 58)T.C.
This is defined as the max amt in grams that are Castorina, PATR 1755(1949XEXPl plasticizers
completely gelled in 2hrs by lg of the substance] for NC) 58a)I. Jullander, Acts Chemica-
 C 118

Scandinavica3, 1309-17( 1949)(A simple method 999-1003(1955) & CA 50, 3036( 1956)( Theological
for the measurement of turbidity applicable to props of NC-NG gels) 76)Anon TM 9.1910
NC SOlnS) 59)A.T.Blomquist& F. T. Fiedorek, (1955), 218-19( Gelatinization of NC)
USP 2485855(1949) &CA 44,3516(1950)
(Nitramines as explosive plasticizers for NC) Cellulose Nitrate, Denitration of. Due to the
60)L.D.Myers&R .W.Webster, USP 2485910 fact that nitration(esterification) of celIuIose is
(1949) & CA 44, 9727( 1950)(Plasticizers for NC a reversible reaction, proceeding as:
obtained by oxidation of unsatd fatty acid esters (CsH702)(OH)3+xHN0~(C5 H702)(0H)3.y
to a degree which renders them compatible with (ON02)Y+XH20,
resins and elastometers) 61)W.H.Woodstock, an equilibrium exists for each concn of nitrating
USP 2497920(1950) &CA 44, 5156(1950)(Alkyl acid, which corresponds to a definite degree of
alkenylphosphonates as plasticizers forNC$ nitration(N content of NC), provided all other
cellulose acetate and ethyl cellulose) 62)H.M. conditions, such as temp & pressure remain the
Spurlin, USP 2510915(1950)&CA 44,9728 same. This means that if the concn of nitrating
(1950 )(Triesters of3-ethyldecane-1,2, 10 bath, contg the product nitrated to a certain N
-tricarboxylic acid as plasticizers for cellulose content, is slightly weakened by addn of water,
esters and ethers) 63)H.G.Reid, USp 2517350 the reaction will go from right to left and NC
(1950) & CA 44, ll173(1950XNonyl esters, will be partly hydrolyzed to the N content
especially the benzoate, chlorobenzoate & corresponding to the concn of the new nitrating
formate as plasticizers for NC & other cellulose bath. This reaction is known as q‘denigration”
derivs) 64)H.A.Aaronson, PATR 1786(1950) The denigration practically does not happen
(Kinetics of soln of NC’S in expl plasticizers) if the acid is rapidly diluted with cooling to a
65) BritCelanese, Ltd, BritP 654771(1951) & CA very low concnj as, for example, when NC wet
47, 605(1953)(Monoethers of 1,4-butaned;ol, with acid is drowned in a large amt of cold w
such as mono-Bu ether, as plasticizers for NC) contg ice. If, on the other hand, drowning is
65a) L. Brissaud & M. LecIercq, MP 33, 473-80 done into a smaH amt of w and the temp is
(195 l)(Electrophotometric detn of turbidity and allowed to rise, a certain amt of denigration will
coloration of NC solns) 66) F. Boyer-Kawenoki & take place. It has been observed, that if
G.Champetier, CR 234, 1053-5(1952) & ,CA 47, during wringing out the spent acid, the NC is
2481( 1953 XFixation of camphor by NC) 67)T. left in contact with humid atmosphere longer
Sakurai=t al, JIndExplosivesSoc, Japan 13, 33-9 than usual, considerable denigration takes place,
& 328-34(1952); CA 49, 273 & 5844(1955) especially in outer layers of wrung NC(See also
(Gelatinization of NC with NG) 68)F.Boyer Refs 5,8 & 14)
-Kawenoki, CR 236, 2315-17(1953) & CA 47, Although NC is an ester, treatment of it
10840( 1953)( Fixation of EtCentr with NC) 69) with usual saponification agents, such as aq
F. J .Masuelli, “A Study of the Reaction of alkalies, does not yield cellulose and an alkali
Cellulose Nitrate with Various Reducing Agents”, nitrate but reaction proceeds somewhat
Doctoral thesis, Virginia Polytechnic Institute, differently, resulting finally in decompn
Blacksburg, Virginia( 1953), 32-5( Salvation) 70) (degradation) products of NC, such as modified
Ott 5, Part 1(1953), 333-4(Swelling of NC) 71) cellulose and their nitrates~ sugars” some
T.Sakurai & Y.Sate, JIndExpls Sot, Japan 14, organic acids, C02, etc together with alkali
111-16(1953) & CA 49, l1283(1955XEffect of AN nitrates & nitrates, and ammonia(See also Refs
on gelatinization of NC with NG) 72)H. Maisner~ 1,2,4 & 14). It is possible, however, to saponify
USP 2690964(1954) & CA 49, 618(1955) NC to cellulose without degradation, if treatment
(Gelatinization of NC with nitroparaffinsy such as is effected by weaker denigration agents Y such as
NMe) 73)G.Desseigne & J .Tranchant, CR 239, by alkaline hydrosulfides, as is used in the
769-71(1954) & CA 49, 11285(1955)(Gelatinization manuf of rayon by the “nitrocellulose process”
of NC with urethanes & substituted ureas) 74) (See also Refs 7,11,14 & 15)
Ott 5, Pt 2(1954), 714-15 (Solvents for NC’S); Other methods of denigration are described
Ibidy I% 3(1955), 1082-5 & 1451-3 [Soly of NC’s in Refs 9,10,12,13,14 & 16(See also Ref 13a)
of various N contents and viscosities in various (This section was reviewed by Dr F. J.Masuelli
solvents; a table based on data of Kraus(Ref of PicArsn)
34) and of Hercules Powder Co, Wilmington, R efs: .l)M.Berthelot, CR 131, 519( 190())(Study
Del] 75)T .Okawa,]ChemSoc, Japan 76, of decompn of NC by alkalies) 2)E .Berl & A.

—.
 C119

Fodor, SS5, 254, 296 &313( 1910)(Denitration (19551 & CA 52, 17799( 1958)(Continuous
of NC by alkalies) 3)R.C.Farmer et al, JCS denigration of NC by NaHS, followed by
117, 815-16( 1920)(Hydrolysis of Cordite & desulfuti?ing) 16)E.P .Swan & L. D. Hayward,
Guncotton) 4)W.O.Kenyon & ‘H. LeB.Gray, JACS CanJChem 34, 858-62(1956) & CA 51, 1047
58, 1422( 1936)(Alkaline decrimpn of NC) 5) (1957 )(Denitration of NC by catalytic
J.Desmaroux, CR 206, 1483(1938)&CA 32, hydrogenation)
5204( 1938)(Denitration of NC by dil acids) 6)M.
Mathieu & T.Petitpas, CR 206, 1485(1938)&CA Cellulose Nitrate Analytical Procedures.
32, 5204( 1938 XDenitration of NC and structure Various analytical procedures for commerical
& soly of resulting products) 7) F. H. Reichel & grade NC’s and for some foreign military grade
A.E.Craver, BritP 512960(1939)& CA 35, 1228 NC’s are given in Refs 1-48. The most important
(1941) USP 2289520(1942)&CA 37, 532(1943) source of info for US commerical grades is in
[Denigration of NC fibers(previously swelled by Ref 48, where the folIowing tests are described
aq acetone) with a reducing agent ~ such as in detail: a)Tests for soluble NC, such as
alkali hydrosulfide in not more than in 3% soln at appearence$ ash, nitrogen by nitrometer method$
20°] 8)K.Fabel, NC 12, 143-6(1941)& CA 38, stability by 134.5° Heat Test, viscosity by
2 199( 1944)(Denitration of NC during centrifuging steel ball method, volubility Y film test and
the product wet with acid may be avoided by toluene dilution test by Method D301 ,pp
excluding air during centrifuging) 9) K. Thinius, 1061-70 in Pt 6 b)Test and specs for NC
GerP 723628(1942) & CA 37, 5590(1943) (Pyroxylin) plastic sheets, rods & tubes in
(Denigration of NC by suspending the moist Method D701 ,pp 227-31 in Pt 9 c)Detn of chain
product in an inert org Iiq and treating the slurry length uniformity by fractional pptn of NC’s in
with an inorg acid chloride) 10)D.O.Hoffman et Method D171 6,pp 1105-11 in Pt 6 and 446-52
al, JACS 69, 249(1943 )(Denitration of NC by in Pt 8
AC20 & Zn in the presence of either HC1 or British military grade(ctService”) NC’s
pyridine) 1 l)F.H.ReicheI & R. T. K. CornwelIY are described in Ref 33. They are prepd by
USP 2421391(1947) & CA 41, 5306(1947) nitration of either cotton(waste or linters) or
(Denigration of NC with an aq soln of an alk wood(in the form of paper or pulp). Nitrogen
reducing agent, such as NaHS, KHS, NH4HS coptent of NC’s ranges from 10.9-11.47. for
or Ca(HS)2 at pH below 12) 12)G.H.Segall & “Low Nitrogen, Soluble NC”, to ca 13.35 for
C. B. Purves, CanJChem 30, 860-71(1952) t ‘Mechanical High Nitrogen NC”. The Brit
(Denigration of NC by suspending it in dry “Pyto”, also called ‘tMechanical Soluble NC”,
pyridine and treating with hydroxylamine, its contains 12.45 to 12.75% N
o-methylethane and their hydrochloride) 13) A) British “Service” Procedures: a) Preparation
M.Soffer et al, JACS 74, 5301-3(1952) of samples. NC may be supplied at various
(Denigration of NC by the action of Li-Al stages of its manuf. The samples are taken wer
hydride) 13a)F.J.Masuelli, “A Study of the and require preliminary treatment before anaIys is
Reaction of Cellulose Nitrate with Various can begin. The whole wet sample is spread on a
Reducing Agents”, Doctoral thesis, Virginia large sheet of clean white paper, rubbed well
Polytechnic Institute, Blacksburg, Va(1953), betw the fingers to break all aggregates, mixed
31-2 [Denigration is a special case of thoroughly and transferred to a clean wide
saponification and is limited to those necked glass bottle closed by a rubber cap or
reactions in which the process is carried out ‘in stopper and Iabelled {‘Prepared Wet Sample”
such a fashion whereby the cellulose is (PWS). About 100g of this sample is placed
regenerated with the least amt of degradation. betw several sheets of clean filter paper and
The denigrated fibers, however still contain from transferred to a hand press where it is
1 to 2% N. Denigration with Na hydrosulfide subjected to heavy pressure for 10 reins. If
proceeds as follows: Ce11-(ON02)z+2NaHS the paper is well satd with w, the operation is
-+Cell+2NaN02+2S] 14)Ott 5, Pt 2(1954), repeated with fresh paper. Then the material is
720-l(Denitration by spent acid); 730-1 & 753 rubbed betw the fingers until free from lumps and
(by acids); 752-3(by alkalies contg reducing transferred to a tray of paper or Al. After
agents); 753(by acid chlorides) & 753(by Li-Al lightly covering the tray with a sheet of fiIter
hydride). Ibid, R 3(1955), 109@ Deni~ation by paper(to protect from dust), it is left at RT for
polysulfides) 15)Wolff & CO, Ge@ 936005 24 hrs. For final drying the tray is transferred to
 C 120

a thermostatically controlled oven to remain until rhe supernatant liq is quite clear(minimum
there for 6 hrs at 50°, The dried NC is 4 days), the total vol of content(V) is read and
transferred to a clean, dry bottle, which is ca 50ml of cIear Iiq is transferred to a tared
closed by a rubber stopper and labelled silica dish, where the solvent is evapd at RT
“Prepared Main Sample’’(PMS) b) Mirzeral and the zesidue is heated at 65° to const wt.
matter(ash). is detd by burning ca 2g of Then the residue is incinerated with paraffin as
“PMS”, mixed with liq paraffin in aPt dish described in test(b) and z of organic matter sol
over a Bunsen burner, followed by incineration in eth-alc is calcd from the formula:
in a muffle furnace at 6000. After cooling, the [(Wt of residue-Wt of ash)x25V] /Vol of liq
residue is wetted with 2ml of 57. Amm. evapd(ca 50ml) g)Soly oj NC of 10.9-12.75%
carbonate soln & heated at 100-105° to const wt N content is detd by treating ca 0.5g of “PMS”
c)Gn’t is detd by digesting the “mineral matter” in the same manner as in the test(f), except
with coned HC1 on a water-bathY allowing the that 100ml(instead of 50ml) of supernatant liq
insol matter to settle~ diluting the liq with an is removed. Then the VOI in the graduate is
equal amt of distd w & decanting thru a No 41 made up wirh more eth-alc soln, followed by
Whatman filter paper. After washing the dish & shaking and allowing to stand overnight. After
filter paper, the filtrate and washings are saved repeating this opern once more? the total
for the detn of “total iron”. The filter paper superna~ant liq is decanted thru a tared
is placed in a Pt dish, dried at 100-105° & then alundum crucible grade RA98 and the residue
ignited untd free from carbonaceous matter. If in the graduate is removed ro the crucible by
any grit is present it is transferred with camel washing with eth-alc. After thorough washing
hair brush thru a small No 36 BS sieve(see of residue with eth-ale, it is dried(in the
Table, p A674, in Vol 1 of this Encycl) and crucible) at 65° to const wt and % org matter
onto a small No 60 BS sieve. The number of sol in eth-alc is calcd from the formula:
particles retained on each sieve & their nature 100- [ 100x(Wt of residue)] /Wt of NC h) Organic
are reported d) Total iron is detd by evapg the matter insoluble in acetone is detd by dissolving
combined filtrate & washings from the “grit” ca lg of ~ tpMS~ ~in 500ml of redistd acet and~
test to below 100ml(if the vol exceeds it), after allowing the soln to stand overnight
transferring the liq to a 100ml vol flask & filtering it thtu an alundum crucible grade
adding distd w to the mark. After pipetting 25ml RA98. After thorough washing of beaker &
into a 50ml std Nessler tube & diluting to the filtering the washings thru the crucibIe, it is
mark with W, add 2ml of 20% citric acid soln$ transferred to a Wiley type apparatus to be
O.lml of thioglycollic acid & sufficient amt of extracted for at least 2 days. After drying the
10% Amm hydroxide to produce a S1 pink color. crucible in air, it is heated in an oven at
After mixing & allowing to stand for 5 reins, 103-105° to const wt. Then the crucible is
the iron content is detd by comparing with placed in a small beaker, the residue is wetted
color standards in a Lovibond tiutometer with 570 Amm carbonate soln and the ensemble
e)Alkalinity is detd by titrating with O. lN Na dried at 100° in the open. After removing the
carbonate soln, in presence of methyl orange crucible from beaker, it is heated at 103-5° to
indicator, 100ml of filtered supernatant liq obtd const wt and loss of wt, on ignition, times 100
after shaking at intervals for a period of 1 hr & gives % org matter insol in acet i)Organic
allowing to settle, ca 10g of “PMS” with 100ml matter soluble in acetone-alcohol is detd only
O. lN HC1 & 100ml distd w and comparing the on NC of low N content(soluble) to be used for
reading with that obtained on titrating a blank purposes ~ther than manuf of solventless
consisting of HCI & distd w shaken in the same proplnts. In this test ca lg of ‘(PMS” and
manner. Alkalinity, calcd as CaC03=(Titre 150ml of solvent consisting of 93 parts by wt of
differencexFactor of O. IN Na2C03 )/10 f)So@ denatured alc(prepd by mixing 100ps by vol of
oj NC of minimum N content 12.75% is detd by 92% alc with 4ps of methanol & 2ps of benzene)
shaking by hand vigorously ca 4g of “PMS” & 7ps of acetone are shaken(in the same manner
with 150ml of 2: l-ether-alcohol in a 200ml as described in test f) in a stoppered tube 43cm
graduate, provided with polythene stopper, long & 2. 5cm in diam and then allowed” to stand
followed by mechanical shaking for 6 hrs on a overnight. If the amt of deposit is small, the
wheel rotating at 15rpm in a water-bath clear Iiq is decanted and the residue is shaken
maintained at 15.5°. After allowing to stand with new 150ml portion of solvent. After alIowing
 C 121

to stand overnight, the clear Iiq is decanted and is prepd by nitration of either wood pulp
the residue is transferred quantitatively to the (Spec JAN-C-216) or cotton(Spec JAN-C-206)
alundum crucible grade RA98, which is then as is described under Cellulose Nitrate$
heated inan oven at 75-78° toconst wt. If the Manufacture. The finished product shall contain
amt of deposit is appreciable, an aliquot portion no adulterants, such as alkali, mercuric
of clear liq is transferred to a tared Al dish chloride or other substances which will mask
and” after allowing the bulk of the solvent to the heat tests in any way. Following are other
evaporate in the open, the final drying to const requirements and tests:
wt is conducted in an oven at 75-80°. The % a)fieat test at 134.5°. The test is conducted as
matter sol in acet-alc=(Wt of residue x100x150)/ described in paragraph F-4g(and in Ref 54,
( Wt of sampIe x Vol of aliquot taken) j)Sul@es Method 404.1) and NC is considered satisfactory
are detd by heating ca 5g of “PMS” with 50ml if the violet color of std methyl violet paper,
coned HN03 in a 400ml beaker until complete 70mm long & 15mm wide, is not completely
dissoln of NC and disappearance of nitrous turned to salmon pink in 25mins, but is
fumes. The soln is treated with lg of recrystd completely changed in 30 reins b)Heat test at
NaC103 in successive smalI portions and, after 65.5°. The test is conducted as described in
evaporating to dryness & allowing to cool, add paragraph F-4h and NC is con~idered
20ml coned HC1 & O.5g NaCIOa and the soln is satisfactory i f the discoloration appeari~ on the
again evzipd. After cooling, the residue is damp portion of std KI-stsrch paper, 1“ ‘long &
removed with a little distd w & the soln 0.37” wide(moistened on upper haIf with 50%
filtered(to remove any insol matter) into the 2nd glycerine-water) takes place in not less than
400ml beaker. Then the 1st beaker is washed 35mins c) Nitrogerz content. The requirements
and the washings are also filtered. The soln for various Grades and Types are Iisted under
in the 2nd beaker is made up to 200ml with Cellulose Nitrate, Military Grades. The test is
distd w and, after adding 3ml of 10% HCl soln, conducted by nitrometer method as described in
heated to boiling. To the boiling soln is added paragraphs F-4a(l)a(l), & F-4a( l)a(2) & F-4a(l)b
slowly 10ml of hot 10% BaC12 soln and: after in Ref 47 & Ref 54, Method 209.3.2 d)Soly in
continuing to boil for 5mins Y the ppt is allowed ether-alcohol. Requirement for Grade A(ca
to digest overnight. The ppt is then transferred 12.6%) & for Grade D(ca 12.O%N) is 99% soly,
quantitatively to a tared Gooch crucible to be while for Grade B(13.35%) & Grade C(13.25
dried in an oven at 103-105° for 1 hr, followed -13.35%) it is not specified. The test may be
by ignition at 800° for 30mins. A blank conducted by volumetric method [paragraph
experiment is carried out at the same time. The % F-4b(2)] & by gravimetric method
sulfate(calcd as H2S04)=(Wt of BaS04 in detn [paragraphs F-4 b(3)a, F-4b(3)b & F-4b(3)c] .
-Wt of BaS06 in blank) x 8.404 k) Settling Test In the volumetric test, Ig sample of dry NC is
is conducted by thorough mixing(by means of a shaken thoroughly in a stoppered Erlenmeyer
round-tipped glass rod) ca 8g of “PMS” with flask with 75ml of alcohol(US Amy Spec 4-1018 or
20ml of distd w in a 250ml beaker. The opern US Navy Spec 51AB) for ca 5 reins and then
is repeated with three addnl 10ml portions of w allowed to stand for 2 hrs. After adding 150ml
and, after addg with stirring another 50ml of ether(US Spec JAN-E-199), the mixt is
portion of w, the slurry is transferred quanti- thoroughly shaken and allowed to stand overnight
tatively to a 250ml graduate(with 200ml mark without removing the stopper. Then the flask
not less than 19cm & not more than 22cm high). is again shaken and the mixt is transferred to a
After making up to 200ml mark with distd w and special volubility tube, 21” long & 1.35” ID,
stoppering the graduatet it is shaken having the lower end constricted for a length of
mechanically for 15mins and then placed for 2“ to an ID of 0.3” and graduated in divisions of
1 hr on a bench free from vibrations. The vol O.lml. After allowing the tube to stand to const
occupied by settIed NC is read and reported as vol of insol material(usually several hrs), the
“settling test” I)Nitrogen content of NC is reading is taken, and if it is O. 25ml or less, the
detd by Method EA32; 132°C -$tability test by materiaI is considered 99% soluble and if the
Method EA15; and 170°F Heat Test by Method vol exceeds 0.25m17 the tube with contents is
EA 15. These methods are not available to us saved for gravirnetric test. When Grade A NC is
at this time examined, the clear Iiq in the soly tube of
B)US Military Procedures. NC for use in proplnts previous opern is siphoned off to the level of ca
 C 122

0.25” from the upper surface of settled material, in a 250ml beaker with ca 150ml of distd w and
without disturbing it. After shaking vigorously, transferring the slurry to a 250ml cylinder,
ether is added to within 3“ of the top and shaking 10” long, provided with a stopper and graduated
is repeated. Then the insol matter is allowed to at 2ml intervals. After washing the beaker and
settle and the clear lig is decanted. This transferring the washings to the cylinder(not
opern of washing & decanting is repeated 3 allowing the VOI in the cylinder to rise to more
times more. After the 4th recantation, the than ca 240ml) the stopper is replaced and the
insol material is washed with 2:1-eth-alc soln cylinder is thorougly shaken. Then the stopper
into a tared Gooch crucible where it is rinsed is removed, the NC adhering to the inner wall of
thoroughly with eth-alc. Then the crucible is cylinder is rinsed until the vol reaches 250ml,
dried in air, heated at 100° to const wt, the stopper is replaced, and the cylinder is
carefully ignited over a free flame, cooled in a thoroughly shaken & allowed to stand for 1 hr.
desiccator and weighed. The loss in wt after The vol occupied by settled NC, after standing,
ignition (A) is considered the wt of insol is reported as c‘fineness” h) Viscosity(No
material and % of soly of NC is equal to: definite requirement). The test is conducted by
[(Wt of sample-A) x 100] /Wt of sample. When treating 20g of dry NC either in a 16-02 wide
Grades B & C are examined, 100ml of cIear soln mouth bottle or in a liter Kjeldahl flask$ with
are drawn from soIubility tube of volumetric test 20g of ale, followed by 160ml of pure absol
(wirhout disturbing the settled material) into an acet and, after stoppering the bottle(or flask),
Al can 50mm high & 90mI in diam provided with a shaking it in a rotating wheel with the bottle
tightly fitting cover. The can is then heated held at 45° to the plane of rotation, until
slightly on top of closed water-bath and 50ml of mixing is complete. The mixt is allowed to
distd w is added gradually with stirring & stand for 24hrs before transferring it to a
continued heating. After NC has been pptd as viscosimeterj which consists of a glass tube
finely divided fibres, the heating is continued 14” long & 1“ ID closed at the lower end with a
until the liq evaporates. Then the can is stopper covered with metal foil and having
heated at 95-100° to const wt. If the wt of two marks exactly 10” apart(2” from each end of
soluble NC in 100ml of clear soln in the can is the tube). The tube, filled to 1“ from the top,
A, and W is four-ninths of the wt of the original is stoppered and placed for at least lhr in a
sample, then 100A/W is equal to % of sol NC water thermostat maintained at 25°. After
e) Acetone insoluhle(max allowed 0.4%). It is removing & wiping the tube, ir is adjusted in a
detd by wetting ca lg of dry NC in a 250m1 vertical position(by means of a clamp & stand)$
Erlenmeyer flask with 10ml alcohol, followed the upper stopper removed and several steel balls
by shaking with 150ml of filtered 99% pure (having diam 0.793 to 0.795” & weighing 2.025
acetone until complete dissolution. The soln is to 2.045g and previously calibrated with a liq
then passed thru a tared Gooch crucible and the of known viscosity) are dropped in succession.
flask is washed with several portions of acet The time required for each ball to pass from one
using the washings for rinsing the residue in the mark to the other is tecorded by a stop watch
crucible. Then the crucible is dried at 100° and the average is taken
to const wt and the increase in wt is calcd to % Requirements and tests for Pyroxylin
of acet insol f) Ash(max allowed 0.4%). It is type NC are described in Specs listed here as
detd by gelatinizing ca 2g of dry NC in a tared Refs 51 & 52 and for Technical NC(for use in
crucible with 57. castor oil soln in ricet and ignit- organic coatings) in Ref 53. Several US std
ing the gel. It is allowed to burn without applying tests are described in Ref 55. In Ref 49 is
heat to the crucible until charred residue remains. described detn of N content of NC by IR
Then the crucible is heated to complete the spectrophorometry and in Ref 5S detn of NC by
ignition, cooled and weighed. If preferred, NC chromous chloride reduction. One of the latest
is digested in the crucible with nitric acid and methods on detn of N content in NC by
then ignited by heating the crucible g) Fineness ferrous-titanous titration is described in Ref 44.
(No definite requirement except that NC shall be This test will be included in the next edition of
uniformly pulped & be free fr...m lumps! strings, US Military Standard Spec
or material of such consistency as ro affect Detn of N content by ferrous sulfate or
proper colliding in the mixers). The test is ferrous ammonium sufate, such as described in
conducted by thoroughly mixing 10g of dry NC Refs ll,12a,37,40 & 43 seems to be rapid and
 C 123

especially suitable for plant control. However, “standard” NC. Transfer 0.6-O.65g of ‘*std”
the use of K nitrate as a “standard” sometimes NC into a tared narrow weighing bottle, stopper
gives low results and makes this method nor as it and reweigh. Remove the stopperY insert
accurate as for example, the nitrometer method. the bottle carefully without upsetting it thru the
The method developed at PicArsn in 1948(Ref neck of a 300ml Erlenmeyer flask contg 150ml
18) is different because it uses as “’standards” of coned H2S04(free from HN03 ) cooled to ca
NC’s of different N contents, previously analyzed 10°. The flask is provided with a rubber
by DuPont nitrometer. As this method was never stopper and a glass rod(ben t at the ‘lower end
published in the literature, it is, for this reason, to an angle of 450), fitting loosely in the
described here in detail. The method is essentially perforation. Stopper the flask and swirl it in a
as follows: a)Prep ‘‘ std” ferrous ammonium rotary manner> keeping it in an ice-bath until
sulfate-soIn(Reagent I) by dissolving, with complete dissolution of NC. Remove the stopper,
stirring, 106.15g of pure hexahydrate in ca 900ml leaving the glass rod in the flask and titrate
of warm soln prepd by mixing I part(by vol) of with Reagent 1, as described under “Standardiz-
coned HzS04(free from HN03) & 2ps of distd w. ation of Reagent I by K nitrate”. When the pink
Cool the soln, make it up to 11 and transfer coloration appears, tip over the weighing
part of it to an automatic SOml Machlett burette. bottle by means of the bent rod and if the liq
One ml of this soln is equivalent to 0.0019g of turns greenish-yel, continue titration until pink
N if ritrated ‘against KNO~ or HN03 b)Prep color is permanent and then “backritrate”
* ‘std” K nitrate soln(Reagent II) by dissolving with Reagent 11 as described in previous test.
13.72g of pure salt(previously dried for 2 hrs at Take reading f)Detn of N content of unknown
100-1 10°) in 11 of distd w and transfer part of sample. Proceed exactly as in previous test
it to a 5ml automatic semi-micro burette. One ml using 0.6-O.65g sample dried in the same manner
of this soln is equivalent to 0.0019g of N. This as “std” NC and if reading is closer to that
soln is intended for use in t ‘back titration” found for “std” Guncotton, use it in calcn;
(See below) c)Prep f ‘std” NC’s by accurately and if reading is closer to that of Pyrocellulose:
detg(by DuPont nitrometer) N contents of pure, use this in calcn. If (a) g of “std” Guncotton
dry samples manufd at the plant, such as contg (n)% nitrogen, require(r)ml of Reagent I
Guncotton, Pyrocellulose or Pyroxylin and keep and if (A)g of test sample require (R)ml of
the ‘ %tds” in jars, tightly closed with rubber Reagent I, then % N in test sample is calcd
stoppers d)StandardizeReagent I by K nitrate. from the formula: n x%x #
Add slowly (from the burette) Reagent I into a Tests conducted at PicArsn for NC’s
wOml Erlenmeyer flask, contg ca 0.6g(accurately ranging from 12.46 to 13.95% N gave on the
weighed) KNOa(previously dried for 2hrs at average results within ~ O.O2% of nitrometer
100-1 100), dissolved in 150ml of coned H2S04 values
(free from HN03 ). The flask is placed in an Analytical procedures for acids used for
ice-bath and is swirled in a rotary manner during nitration of cellulose will be described under
titration. The tip of burette is kept inside the Mixed Acid, Nitric Acid and Sulfuric Acid
flask without touching the surface of liq. The R efs: l)A.Logothetis & G. Gregoropoulus, SS
speed of addn is regulated so as to allow the 16, 1-2( 1921)(A rapid method of detn of water
pink coloration, due to the formation of content in wet NC) 2)E .Knecht & E. HibbertY
hypothetical complex “FeS04.NO”, to disappear ‘ ‘New Reduction Methods in Volumetric Analysis”
on swirling as soon as it is formed. No Longmans Green & Co, London(1925), 101
accumulation of the reagenr on the surface of the (Titanou$ chIoride method for detn of N content
Iiq in the flask is permitted, to prevent possibIe in NC) 3)H.Muraour, BullFr [4] 45, 1189-92
oxidation of the ferrous ion by air. The (1929) & CA 24, 1597(1930)(Detn of nitrate N in
titration is continued until rhe appearance of a NC & smokeless proplnts by dissolving the
permanent pink color. Remove the flask from sample in acetone, adding HZ02, NaOH,
the ice-bath and “back titrate” the soln with NaB02.H20 and treating with Devarda alloy)
Reagent II until the color turns back to greenish 4)A.J.PhiHips, IEC, AnalEd 7, 416-19(1935)
-yel. Take reading and see if one drop of (Detn of the fineness of NC by dye absorption
Reagent I turns the soln S1 pinkish. If not, method) 5)E.Berl et al, IEC, AnalEd 10,
take the last reading and add another drop of 219-24(1938) & CA 32, 4338( 1938) (Stabilization
Reagent I e)Standardize Reagent I by and stability tests of NC) 6)S.cott & Furman
 C 124

( 1939), 650-2(Detn of N content using DuPont ChimInd, Bruxelles, Belgium 3(1954) & CA 50,
nitrometer) 7)C.J.Maim et al, IEC, AnalEd 14, 7479( 1956)(Detn of N content in NC) 26)J,
292-7(1942) & CA 36, 2716( 1942) (Analysis of Tranchant, Ibid 3(1954) & CA 51, 1607(1957)
mixed cellulose esters using partition method; (Titanometric detn of N content in NC) 27)P.
review of previously used methods of analysis) Miaud, MP 37, 465-97 (1955 )(Detn of water in
8)Clift & Fedoroff vol 1(1942), chap 12,pp 10-11 NC cakes by means of high-frequency current)
& VOI 2(1943),PP 15-23 (Various NC tests) 9) 27)H.Stalcup & R. Williams, AnaIChem 27, 543-6
Davis(1943), 268-9( Stability tests); 269-73 ( 1955)(Volumetric detn of NC & NGu by
(Detn of N content by nitrometer) 10)Kast transnitration of salicylic acid) 28) Ott vol 5,
-Metz( 1944), 183-261 (Various chemical & part 3(1955), 1394(Detn of viscosity of NC);
physical tests for NC) ll)B.N,Mitra & M. 1407(Detn of N content); 1411 -13( Stability
Srinivarsan, J IndianChemSoc 21, 397-8(1944) & tests); 1414 -15(Detn of impurities, such as ash,
CA 39, 4487( 1945) (Application of ferrous acidity, alkalinity, sulfur & chlorides in NC);
ammonium sulfate to detn of N content in 1416(Detn of density) 29) T. C. Castorina, PATR
Gun cotton) 12)A.D .Shikher Rusp 67715(1946) & 2107( 195 5)( Radiometric method for detn of
CA 43, 3197( 1949)(Detn of stability of NC) 12a) sulfate in crude NC) 30)E .Thonert & F .Lobato,
P .Hosken et al, PicArsnChemLabRept 119743 Explosivst 1955, 109-13 & CA 51, 9160(1957)
(1947 )(Detn of N by ferrous ammonium sulfate) [An automatic detn of stability of NC, proplnts
13)M,LArkhipov et al, ZhPriklKhim 20, 773-80 & expIs by the radicaIIy modified method of
(1947); 21, 1107-13(1948) & 22, 385-91 & Grotanelli, which was described in MemAccad-
1030-6(1949); CA 42, 5669(1948); 43> 9435(1949); Italia, Chim 2, No 6, 5-17(1931) and abstracted
43, 9436( 1949) & 44, 2233( 1950) (Methods of in CA 26, 2866(1932)] 31)P. Verschragen~
detg viscosity of solns of cellulose & NC) 14) AnalChimActa 12, 227-30( 1955) (Comparative
G. Foges & G. Krishnaswamy, JIndianChemSoc investigation of N content detns by methods
24, 313-20(1947) & CA 42, 5673( 1948)(Detn of the of Sch16sing, Lungel Leclercq & Math~ and
fineness of NC pulp) 15)Dor<e(1947), 241-50 Devarda showed that Sch16sing’s method gave
(Tests for NC) 16)L.Brissaud, Ml’ 30, 201-4 the most consistent results. The Schlosing
(1948 )(Detn of the fineness of NC by means of a method is described by Kast-Metz(1944), 217)
Swedish apparatus called “Flour Tester”) 32)W.C.Easterbrook & R. H. Mathew, Imperial
17) L. Brissaud, MP 30, 211-16( 1948) (Volumetric Chemical Industries, Ltd, Nobel Division Report
detn of H2S04 in NC’s using Ba thiocyanate as i?l-5470(1956)( Review of methods for N detns
an indicator) 18) B. T. Fedoroff, PicArsnChem in NC) 33)fdinistry of Supply, GtBritain,
LabRept 122871 (1948)( GenLabFi1e 11 23) “The Examination of Nitrocellulose”, Method
(Rapid method for the detn of N content in NC’s EA22, OIN 14950(1956) 34) E. Biasotto Mano &
by the ferrous ammonium sulfate method, using L. C. A. Cunha, Lima, RevQu(mInd(Rio de Janeiro)
as rhe “standard” a NC of known N content, 25, NO 290, 17-19(1956) & CA 51, 4215(1957)
previously detd by nitrometer) 19)K.Thinius, (New color reactions for cellulose, NC,
Farbe u Lack 56, 3-9(1950) & CA 44, 4817 cellulose acetate & other cellulose derivs)
( 1950)( Luminescence analysis for identification 35)P.Lhoste, Mp 39, 209-14( 1957)(Detn of
of NC, cellulose, cellulose acetate, ethylcellulose sulfuric acid in NC) 36)J .Grodzinski, Anal-
& methylcellulose) 20) L. B. Genung, AnalChem Chem 29, 150-2(1957) & CA 51, 3999(1957)
22, 403(1950) & CA 44, 6121( 1950)(Detn of N (Detn of N in NC by ferrous-titanous
content by nitrometer) 21)R.Leclercq & J. t itrimetric method) 37)S.Sandi & G.F lanquart,
Math~, BullBelg 60, 296-300(1951) & CA 46, ChimAnal(Paris) 39, 20-4(1957) & CA 51, 7943
423 2(195 2)(Detn of N in NC by ferrous ( 1957)(Detn of N in NC, NG, PETN, etc by
ammonium sulfate method) 22)W. E .Shaefer & titration with ferrous sulfate soln using the
W.W .Becker, AnalChem 25, 1226-31( 19S3) dead-stop end point method) 38)Y.Lacroix er al,
(Modified ferrous-titanous meyhod for detn of MP 39, 459-68(1957) & CA 52, 19688(1958)
N content) 23) OrgAnalysis vol 2( 1954), (Detn of N in NC by Devarda method) 39)R.D*
97- 122(Detn of nitrate N content by various Sarson, AnalChem 30, 932-7(1958) & CA 52,,
methods) 24) T. H. Smith, NorskSkogindustri 11425(1958)(Detn of NC in expl & propInt mixts
(Norway) 8, 402-8( 1954) (in Engl)(Fractionation by nonaqueous titration as an acid in
of NC’s accdg to the degree of substitution) dimethylformamide) 40)J ,~ime~ec, Chem
25)R .Buess et al, ComptRend27eCongrIntern- Pr~mysl 7, 285-9(1957) & CA 52, 12675( 1958)

m
 C 125

(Modified ferrous sulfate titration method for filtering are repeated twice with 50ml AcOH and
detn of N in org nitrates, such as NC) 41)J.L. once with 50mI dist w. Then the residue in the
Garden & B. Leopold, AnalChem 30, 2057-60 flask is transferred quantiratively( using a
(1958) & CA 54, 2735-6( 1960)(Colofimerric stream of hot w) to the same crucible, the
detn of N in NC by the phenoldisulfonic acid contents in crucible are washed with two 40mI
method) 42)T.Murakami, B unsekiKagaku portions of hot w and crucible is dried in an oven
(Japan) 7, 304-9(1958)&CA 54, 3065(1960) at 100-1050 to const wt. Percentage of
(Acidimetric detn of N in NC and in mixed NC=(100A/W)-B, where A is gain in wt of
acids) 43) A. F. Williams & J. Brooks, crucible, W wt of sample and B wt of material
ProcInternAympMichrochem, Birmingham Univ insol in AcOH or w(such as graphite or carbon
1958, 430-7 & CA 54$ 19306(1960)(Detn of N in black)] ; Method 404.1 (Detn of stability of NC &
NC by titration with ferrous ammonium proplnts by 120 & 134.5° Heat Tests); Method
sulfate in strong sulfuric acid soln) 44)R.H. 406.1 (Detn of stability of NC by Taliani test);
Pierson & E.C.Julian, AnalChem 31, 589-92 55)C.C.Jamison, PATR(In Preparation)
(1959) & CA 53, 17512( 1959)(Detn of N in NC (Quantitative detn of nitrogen in NC by chromous
and in smokeless proplnts by modified chloride reduction) 56) F. Feigl, ChemAnal 52,
ferrous-titanous titrimetric method) 45)H.M. lNo 2, 47-9(1963) [Spot test detection of LNC is con-
Rosenberger & C.J .Shoemaker, AnalChem 31, ducted in two operations: a) The nitrate group is
131 5-17(1959) & CA 53, 22914( 1959 XInfrared detected by fusing the sample with benzoin(mp
detn of NC in mixts of cellulose resins) 46) 1379 and testing the evolved gas for nitrous acid
J. D.MuIlen, AnalChimActa 20, 16-19(1959)& by means of the Griess reaction(ie red color in an
CA 53, 22953( 1959)(Detn of N in NC by modified acetic acid soln of sulfanilic acid and l-naphthyl-
titanous chloride method) 47)B .T, Fedoroff et amine) b)The cellulosic component of NC is de-
aI, PATR 2700, VOI 1(PB No 171603),pp t ected by the appearance of an orange color when
A373 to A378(Nitrometer method for detn of N the sample is warmed with thiobarbituric acid,
in nitrates, applicable to NC) 48)ASTMStds HJ. C(: 0).NHt C(:S).NH. $20, and 85% phosphoric
.—.—
(1961), parts 6,8 & 9(Various tests for NC) acid. Both procedures are described in detail]
49)H.Levitzy & G. Norwitz, Frankford Arsenal
TechRept 162=3=1, Philadelphia, Pa( 1961 )(Detn Celmonite. A Favier type mining expl which
of N in NC by infrared spectrophotometry) 50) passed the Buxton Test(Brit): AN 67, TNT 12
US Joint Army-Navy Specification JAN-N-244(2), & NaCI 21%
Nitrocellulose(For use in expls & proplnts) 51) Re/: Marshall 3(1932), 119
US MiIitary Spec MIL-C-15567(BuOrd), Cellulose
Nitrate, Plastic (Celluloid or Pyroxylin Type(For Celsius, Anders ( 1701-1744). Swedish astronomer,
use in powder wads & spacers and in fuzes~ known for invention of “centigrade” thermometer,
tracers & primers) 52)US Joint Army-Navy Spec- also known as “Celsius” thermometer
JAN-C-801, Cellulose Nitrate, Plastic(Pyroxylin) Re/: EncyclBritannica 5(1952), 101
Rods(For use as a fuel component for igniters)
53)US Military Spec MIL-C-5538A, Nitrocellulose, Celtite or Zeltit. A coal-mine expl invented by
Technical(For use in organic coatings) 54)US Dr R. Nahsen & Co, Hamburg and formerIy per-
Military Standard MIL-STD-286A(1960); Method mitted for use in Brit coal mines, having passed
209.2 .2(Detn of NC content in expls & proplnts the Woolwich Test. Its compn was: NG 57, NC 8,
by subtracting from 100%, the sum of percentages K nitrate 19, wood meal 9 & Amm oxalate 12
of other ingredients as detd by appropriate parts
methods); Method 209.3 .2(Detn of N content in R e/.’ Marshall, Dict( 1920), 20 [Compare with
NC using DuPont nitrometer method); Method Naotim, NG(1928), 409]
209.6,2 [Detn of NC(of not less than 12.2% N
content) in proplnts by extraction with 65-70% Cement and Concrete in Ordnance. The term
ACOH is conducted as follows: About lg of dry cement, which in eludes a great variety of ma-
sample is refluxed in a 250ml Erlenmeyer flask terials, refers here only to the hydraulic
with 100ml of 65-70% ACOH for 30mins on a material (mairdy Portland cement) and the term
hot plate and the hot supernatant Iiq is concrete refers to mixts of cement with sand,
decanted thru a tared filtering crucible using gravel, broken stones, etc. and sufficient w to
suction. Operations of extraction recantation & cause the cement to set. If steel rods are used
 C 126

in combination with concrete, the resulting Cement, Acid-Resistant. See under Acid-Re-
tnaterials is known as ‘reinforced” or <‘armored” sistant Materials in VOI l,PP A92-A93 of this
concrete(Refs 1,2 & 7) Encyclopedia
In additic-. to using these materials for
construction of various bldgs for Ordnance plants Cement for Laboratory Use. A Cement similar to
or for construction of fortification s(pill boxes, DeKhotinsky commercial product may be prepd by
etc ), cement and concrete(except the reinforced) heating, with frequent stirring, at not over 140°,
(Refs 8 & 9) were used for manuf of ammo, such 3 lbs shellac scales with 1 pint of North
as landmines, bombs, mortar shells and hand Carolina pine-tar oil, followed by pouring the
grenades. This was done in order to save iron, resulting uniform mixt into molds of the desired
which was a critical material in some countries shape
during WWI & WWII, but it seems that items Re/: InorgSynth 1(1939), 189
which were tequired to produce blast effect
rather than fragmentation could conveniently be Cement, Pettman. A mixt of iron oxide, shellac!
made of concrete alcohol, rosin, ethyl cellulose & pine tar) used
Some of the cement or concrete ammo items to seal fuzes etc. in projectiles
used during WWII by the Czechs, Germans, Re/: l) Glossaty of 0rd(1959), 63 2)US Joint
Italians and Japanese are listed in Refs 3,4,5 & 6 Army-Navy Specification JAN-C-99(1)
Re/s: l)Kirk & Othmer 3(1949), 411-499 2)
EncyclBritannica 5(1952), 104-11 & 6( 1952), Cement, Pyroxylin. A mixt conrg pyroxylin
207-12 3) Anon, “German Explosive Ordnance”, (collodion cotton), a solvent and a plasticizer;
TM 9-1985-2(1953), 39-43( Concrete Bombs, used for cementing NC plastics to other materials
12kg, 50kg & 250kg); 6@5(Concrete practice Re/: CondChemDict(1961), 238
Bombs, 10kg, 50kg, & 250kg); 83(BLC 50
Photoflash Bomb with cement ballast); 277-78 Center-Fire Cartridge. See under CARTRIDGE,
(Concrete A/P Stockmine and Concrete A/P Ball AMMUNITION, Small-Armis Cartridges
Mine) 4)Anon, “Japanese Explosive ordnance”,
TM 9-1985-4(1953), 26 [ 15kg Bomb, Concrete CENTRALITES
(with steel pellets set in)] ; 27-8(10kg & 30kg Introduction. The term “Centrality’ ‘( Zentralit or
Concrete Substitute Bombs); 29(4kg Practice Centralit in Ger; Centrality in Fr & in Ital;
Bomb with concrete nose); 228 [ l-lb Hand Centrality in Span and Tsentralit in Rus) is
Grenade with body made of pottery clay, derived from the name of the “Central Laboratory
glazed or unglazed)(There is no reason why for Scientific & Technical Research at Neubabels-
pottery body cannot be substituted by concrete berg, Germany (Zentralstelle fiir wi ssenschaftlich
body) 5) Anon, “Italian and French Explosive -technische Untersuchungen ZU Neubabelsberg),
Ordnance”, TM 9.1985-6(1953), 2(Ital 3kg A/P where these compds were first investigate~
Bomb with part of the body made of concrete beginning ca 1906(Ref 8). The term “CentraIite”
with steel fragments embedded in it); 21(Ital 5kg usualIy designates some N, N’-dialkyl derivs of
Vento-Marker with part of the body made of carbanilide(sym-dipheny lurea) ,which were found to
concrete), 23(Ital 3kg AA Bomb with concrete be suitable for use as solid non-volatile,
body contg steel pellets embedded in it) 6)H.H. gelatinizer-stabilizers in smokeless proplnts.
Bullock, Museum, PicArsn [Czech 210 Mortar These substwces, the most important of them
Shell(Outer body made of steel 1/8” thick, the Centrality l(Ethyl Centrality) or N, N’-diethyl-
inner casing 1/32” thick and betw them concrete carbanilide, also possess the property of
body, I 9/16” thick with steel fragments em- reducing the temp of burning of ,proplnts, thus
bedded in it) 7) R. F. Blanks & H. L. Kennedy, acting as a flash-reducer. Being neutral,
~QTechnology of Concrete and Cement, VO1 L Centralizes can be used in proplnts contg NG
Wiley( 1955) 8)ASTM Standards(1961 ), Part 4 For incorporation in smokeless proplnts,
(Specs for various cements and concrete) 9)US Centralizes are tisually dissolved in a volatile
Military and Federal Specifications for cements solvent(such as alcohol) and the soln is added to
used by Armed Forces are listed in “hdex of the mixer contg the proplnt slurry. If the proplnt
Specifications and Standards”, US Dept of is going to be “solvent type”( such as Cordite or
Defense, Washington 25, DC, part 1 with 13allistite), the slurry consists of NC, NG & a
Cumulative Supplement dated 30 July, 1961 volatile solvent(such as acetone) and if it is to be
 C 127

‘tsoIventless type’ ‘(such as rocket propInts), and transferred to a large separator funnel.
the slurry contains NC, NG & water After discarding the Iower(aqueous) layer, the
The term C‘Centrality” was recently upper(organic) layer is washed twice with 400g
extended to incIude one of the alkylaryl portions of 4.5% aq HC1 at temp of 80°(to
- carbanili des prepd in France( see Centrality 4). eleminate any alkalinity), followed by four
There is also Butyl centrality to which ‘no washings with w at 80°(to eliminate chlorine
numerical designation has been given(See ions). The crude product is melted in a flat
Centrality, Butyl) dish and kept at ca 80° in a vacuum oven until
the product is dry. This treatment also removes
nearly completely, any monoethylsniline which
Centralite 1 or Ethyl centralite(US); Carbamite may remain as impurity after washings. This
(Brit); Cerztralit 1 or Zentmlit ](Ger); Mollit 1 method is claimed to give a product with a mp ca
(Ger trade name for product used as a 72.3° and a yield of 89%, based on monoethyl=
pi asti ci zer); N, N ‘- Dietbylcarbani/ide or aniline used. The impurities in Centr I should
N, N’-Die~hyI.N, N’-di@enylure~ OC [N(C2H5).- not be more than O. 005% of chlorine and 0.04%
C6H5 1~; mw 268.35, N 10.44%; coi trysts of secondary amine
(from ale); mp 72.4°(790 is given in Refs 1, 2, Mechanism of stabilization of proplnts by
19, 22 & 30); subIimes above its mp, but not as Centr 1 and its gelatinizing and stabilizing
easily as does camphor, bp 325-30°; volatile powers are discussed in Refs 3,5,9,12,13,14,18,
with steam(Ref 19); d 1.x4 at 25 °(detd at 20,21,23,26,27,28,30,31 & 33. Formation of
PicArsn); d 1.12 at,20°(Ref 39); Q: 8409.3 complexes of Centr I with -various substances
cal/g(Refs 15 & 24); Q? 97.5 cal/g(Ref 24) & are given in Refs 7,10,32,35 & 38. Recovew
94..4 cal/g or 25.3 kcal/mole(Ref 32a); Q! of Centr 1 and of other compds from double-base
31.9 kcal/mole(Ref 32a); calorific constant(h) proplnts is described in Ref 36. Synthesis of
-24.4 CSI per 0.0 Ig of Centr 1 which corresponds various compds which are formed from Centr 1
to calcd calorific value at con’st pressure 2253 during the aging of double-base proplnts is
kcal/mole at 17°, vs experimental value described in Ref 29. Binary rnixts and
2264,6kcsf/mole( Ref 25). Its soIy in various org molecular combinations of Centr 1 with various
solvents was detd by Desvergnes(Ref 6) and at compds are discussed in Refs 7,10,11 & 35.
PicArsn. Soly of Centr I in 100g of water: Addnl information on Centr 1 may be found in
3mg at 0°, 8mg at 20°, 12mg at 50° and 30mg at Refs 4,8,16,17,19 & 24
85°; soIy in 100g of absol alcohol: 72.67g at Uses: After WWI it was manufd in Ger under
20° and 515.2g at 50°; 0.584g of Centr I dksolves the name of Mollit 1 for use as a plasticizer
in lg of acetone at RT and 0,877g dissolves (Ref I, p[238] & Ref 4). Its use as
in lg of solvent consisting of 63% acetone & 37% gelatinizer-stabilizer-flash reducer in smokeless
alcohol. Centr is also sol in glycerin and in NG proplnts was already mentioned under
Centr 1 was first prepd in 1876 by Michler CENTRALIZES, Introduction. It has also been
et al,(Refs 1 & 2) by heating ethylphenyl- used as an age-retarder in vulcanized rubber
carbamyl chloride with monoerhylaniline at (Ref 39)
130° or by heating diethylaniline with phosgene, When used in proplnts in smalI quantities
under pressure. Vaganay & Wevert patented the (ca 1%) Centr I acts only as a stabilizer, while
metiod(fif 34), which, when reduced to a larger qusntities(3-it)%) are -used when it is
Laboratory scale, is as follows: required to act also as a gelatinize for NC and,
In a I liter round-bottom flask(provided with sometimes, as a flash-reducer(Ref 37)
a stirrer and pIaced in an ice-water cooling Following are examples of proplnts contg
bath), contg 450g of 7% aq NaCl soln & 363.5g Centr I: a)Ger, single-base: NC( 13.1% N) 93.5,
of monoethylaniline, CG H~.NH(C6H5 ), cooled to Centr 2.8, Acardite 0.6, graphite 1.5, K sulfate
0-4°, is introduced slowly(for ca 3hrs), blow 1.1 & unaccounted 0. 5%(Ref 37) b)Ger PETN
the surface of liquid, 163g phosgene, while proplnt: NC(13.2% N) 56.0, PETN 34.0 &
stirring and maintaining the temp below 4°. The Centr + DNT 10%( Ref 37) c)Ger double-base:
resulting slurry, contg in suspension ethyl- NC(12.5% N) 58.1, NG37.2, Centr 3.9, K sulfate
phenyIcarbamyl chloride, and in soln ethylaniIine 0.3 & unaccounted 0.5%(Ref 37) d)Ger, double
chloride, is stirred for addnl 30mins and transferred -base: NC( 12.9% N) 59.6, NG 39.0, Centr 0.7,
to a flask of 1.5-1 capacity contg 412g of 33% aq graphite 0.1 & unaccounted 0.6% e)Ger,
NaOf{ Soln. The Mixt is heated for 3hrs at S(JO
 C 128

double-base: NC(12.3% N) 64.0, NG 30. O& Centr power) 4)Naoiim, Expl S( 1927), 103( Centralizes
6. O%(Ref 37) f)Ger, double-base: NC(12.2% hi) 1,2 & 3 were manufd in Germany after WWI, by
63.0, NG 28.0 & Centr 9. O%(Ref 37) g)Ger, the firm Weiter-tet-Meer in Uerdingen am Rhein
double-base: NC(12. I% N) 65.1, DEGDN 31.5, under the names MoHit 1, Mollit 2 & MoIlit 3)
Certtr 2.7, graphite 0.3 & K sulfate 0.4%(Ref 5)H.L6corch4 & P. Jovinet, CR 187, 1147-8(1928)
37) h) Ger, double-base: NC(1 1.9% N) 65.0, & CA 23, 3345( 1929)(Mechani sm of stabilization
DEGDN 23.2, Centr 8.8, graphite 0.1, K su!fate of double-base proph-rts by Centr 1 & DPhA. It
1.5 & unaccounted 1.4%(Ref 37) i)Ger proplnr was concluded that Centr 1 is a better stabilizer
S6702: NC(12.0% N) 29.5, DEGDN 29.5, AN than DPhA when in presence of NG) 6)L.
40.0 & Centr l. O%(moisture ca 1.1% is not Desvergnes, Ann ChimAnalChimAppl 10,226-8
considered)(Ref 37) j)Brit Cordite N: NC(13.1% N) ( 1928) & CA 22, 4034( 1928)(Soly of Centr 1 in
19.0, NG 18.5, NGu 54.7, Cenrr 7.5, & cryolite org solvents) 7)L .M<dard, MP 24,174-210
(K3A1F6) O.~% with chalk 0.15% added(Ref (1930- 3 I)(Study of mo! ecul ar combinations of
24~p 107) k)Amer, H-4 rocket proplnt: NC 58.0, Centr 1 with various compds) 8) Stettbacher
NG 30.0, DNT 2.5, Centr 8.0 & K sulfate (1933), 197( Centralizes 1 & 2 were first
1.5%(Ref 24a,p 153) I)Amer, JPT rocket proplnt: investigated in Germany ca 1906 as possible
NC(13.25% N) 59.0, NG 40.0 & Centr 1.0% and stabilizers for NC in smokeless propInts) 9)M.
added DPhA 0.2 & nigrosine dye O.l%(Ref 24a,p Giua & M. Guastalla,Chim & Ind(Paris 29, 272-7(1933)
153) m)Amer, M5 cannon proplnt: NC(13.25% N) (Action of stabilizers, including Centr 1, on NC,
81.95, NG 15.0, Ba nitrate 1.4, K nitrate MNT, DNT, TNT, PA & some other expls) 10)
0.75, Centr 0.6, graphite 0.3, residual alcohol L.M~dar~ Chim & Ind(Paris) 30, 277-80( 1933)
2.3 & residual water 0.3 patcs(US .Spec JAN-P-323) (Discussion on possibility of existence of
n) Amer, M15 cannon proplnt: NC( 13. 15% N) 20.0, complex DPhA- EtCentr) l.l)T.Urbm’ski, Rocz-
NG 19.0, NGu 54.7, Centr 6.o, cryolite 0.3 & Chem 13, 399(1933) & 15, 191(19351 CA 28
residual .alc 0.3%(US Spec MIL-P-668A) o) Amer, 27(1934) & 30, 2834( 1936)( Binary mixts of
M17 cannon proplnt: NC( 13.15% N ) 22.0, NG EtCentr with HNMnt, eutectic point 52. 1°; with
21.5, NGu 54.7, Centr 1.5, cryolite 0.3 d PETN 68° and with Eryrhritol Nitrate 42.2°)
residuaI SIC 0.3%, with graphite 0.1% added(US 12)M.Tonegutti, SS 32, 300-5(1937) & CA 32,
Spec MIL-p-668A) p) Amer, M7, mortar& small 1099( 1939)( Stabilizing power of Centr 1 detd by
arms proplnt: NC(13.15% N) 54.6, NG 35.5, methods of Taliani or Thomas compares closely
K perchlorate 7.8, Centr 0.9, carbon black with those for DPhA and Acardite) 13)T.
1.2 & residual SIC 0.8%(LN Sfec JAN-p< 59) Urbahski & W.Miladowski, SS 33, 247(1938) &
q)Amer, M9, mortar & smali arms proplnts: NC CA 33, 385( 1939)(DP hA was shown to be a better
( 13.25% N) 57.75, NG 40.0, K nitrate 1.5, Centr stabilizer for NC than Centr 1) 14)R. Dal bert,
0.75 & residual alc O. 5%(US Spec MIL-P-20306) MP 28, 147- 55(1938) & CA 33, 7569(1939)
r)US, T18, recoilless rifle proplnt: NC( 13.15% N) (Comparison of doublebase proplnts stabilized
72.0 NG 19.75, Ba nitrate 0.75, K nitrate 0.7, with Centr 1~ DP hA or carbazol e showed that
Centr 6.5, graphite 0.3, residuaI alc 1.2& denigration of NG & NC and Iowering of viscosity
residual water 0.3 parts(Pic Arsn Spec PA-PD of ptoplnt were I east with Centr 1) 15) E. BurIot,
-329) s )US, T28 recoilless rifle proplnt: NC MP 29, 25 l(1931)(Some props o-f Centr I) 16)
(13. 15% N), 6%25, NG 25.0, Ba nitrate 0.75, Tho~e 4(1940), 521(Some props of Centr I)
K nitrate 0.7 Centr 6.o, graphite 0.3, residuai 17) Davi< 1943), 319( Centr 1 has superseded
alc 1.2 & residual water 0.3%(US Spec Centr 2 for use in smokeless proplnts) 18) Alvaro
OAC-p D-134 )( See also Centrality 1, Analytical Alberto, AnaisAcadBrasilCienc 16, 31 1-2(1944)
Procedures; Centrality 1, Nitro Derivatives of; & CA 39, 3160- l(1945)(Stabili zing power of
and Centrality 1, Transformation Products, Formed Centr 1 in double-base proplnts) 19)Kast-Metz
During Aging of Propellants Containing It) (1944), 165 [Some Fops of Centr 1] 20)L.
Re/s: l)Beil 12, 422 & [238] 2) W.Michler et al, Pauling, OSRD Rept 4821(1945) [Thermal
Ber 9, 712 & 1913(1876) 3) T. L. Davis, IEC 14, stability of trench mortar sheet proplnts such
114 1( 1922)( Gelatinizing power of Centr 1 for as those contg(approx): NC(ca 13.22% N) 52.2,
straight NC proplnts is higher than that of NG 43.0, DEtPh 3.o, EtCentr 0.6 & K sulfate
Centr 2, but lower than ButyIcentralite. It seems 1.2%, were better than of similar proplnts contg
that the heavier the alkyl group in substituted DPhA] 21)L.Pauling,OSRD Rept 5418(1945)
{lphen ylureas, the greater is the gelatinizing (Thermal stability of Ballistite type ptoplnts
..
contg EtCentr did not seem to be better than of

.
 C 129

those contg, DPhA. Incorporation of DEtPh in 2111 2(1958 )( Recovery of Centr 1 and other compds
Centr contg proplnts improved their stabi!ity) from double-base proplnts) 37)B.T.Fedoroff et al,
22)P ;rez Ara( 1945), 423(Some props of Centr 1) PATR 2510(1958) pp Ger 27 & Ger 141-5 37a)
23)A11 & En Expls(1946), 42( Centr I acts in M.Giua et al: CTrattato di Chimica Industrial”,
propln~s as gel atinizer for NC and as stabilizer UTET, Torino 6, (1959), 363-4 38) G. Ch#rubin,
& a ash-reducer) 24)H.Muraour & G .Auriis, MAF JChimPhys 57, 361-73(1960) &CA 54, 21938
20, 433( l$M6)(Some pops of Cerztr 1) 24a) (1960)(Intermol edar linkage betw Centr 1 &
“Summ sty Technical Report of Division 8, NC) 39)CondChemDict( 1961), 375( Props & uses
NDRC~VoI 1(1946),107 25)J .Tay!or et d, of Centr 1)
JPhysCoHChem 51, 590-l(~947)(Calorific
constant and calorific value t%r Centr 1) 26)P. F.
Macy, PATR 1641(1947) [Investigation of Centralite 1 Analytical Procedures. Centr I can
stabilizers for doubl &base proplnt(mcket, trench be detected by various calorimetric tests, such as
mortar & artilI cry), showed that carb azole, described in Refs 1,6,12,2428 & 33. Some other
asym-DPhUrea and Centr 1 are better stabilizers qualitative tests are given in Ref 13. Quantitative
than DPhA) 27) R..Drdbert & H. FicherouIf e, MP detns of Centr I by” bromination methods are
30, 283-300( 1948) (Investigation of various org described in Refs 4579 )399 10,14,16,17,20,27,34 &
compds from the point of view of their 35. Chromatographic and spectrophotometric
utilization as st abilizers-gelatini zers in smoke- methods are found in Ref.s 11,15,18,21,22,23,24,
less proplnts to replace Centr 1 or DPhA showed 29,30,32 & 33. Other quantitative methods,
that the fallowing compds might prove of interest: including polarographic, are in Refs 2,7a,20a,25,
2-acetyIphenanthrene, butyloxal ate, carboxybutyl- 26,27 & 30. X-ray diffraction spectra data are
morpholine, carboxyethylmorpholine and given in Ref 19. Dems of stabilizing action of
ethylene- 1, 2-diureth ane) 28)A. G. Garc~a Centr 1 by methods of Taliani and Thomas are
-Guti6rrez, Ion(Madrid) 9, 165-71( 1949)& CA discussed in Refs 3 & 8
43, 6825( 1949)( Review of substances, including The following qualitative tests for EtCentr
Centr 1, used as stabilizers in smokeless has been used at PlcArsn:
proplnts) 29)P.E.Wilcox & W.A,Schroeder, JOC a) Potassium Bichromate CoIor Test. To ca lmg
15, 944-9( 1950)(Synthesis of various compds sample placed on a spot plate, are added, while
formed from Centr 1 during the aging of double stirring, 3 drops of coned HzSO, and ca Img of
-base propInts) 30)W.R.Grassie et al, CanJ Res K2Cr207. A raspberry-red color indicates the
28f3, 468-84(1950) & CA 45, 3594(195 l)(Stabilifing presence of Centr
props of Centr I in comparison with possible new b) Coned Srdfuric-Dilute Nitric Acid Color Test.
stabilizers for NC) 30a)W.A. Schroeder et al, To ca lmg sample placed on a spot plate are
AnalChem 23, 1743( 1951)(UV & visible added while stirring 3 drops coned H2S04 and
absorption spectra) 3 l) Stettbacher, PoIvoras( 1952)$ 1 drop dil HNOa(6 drops coned HNOa to IOOml
(Gelatinizing power of Centr 1 is reported to be distd water). A raspberry-red coIor indicates the
lower than that of Acardite or DPhA, but higher presence of Centr
than DPhUr.ethane) 32) F. Boyer-Kawenoki, CR c) Precipitation as Dibromocentralite Test. To ca
236, 2315-17(1953) & CA 47, 10840 (1953 )( Fixation 100mg sample dissolved in 5ml glacial AcOH are
of Centr 1 in cycloh exane by NC of 12% N) 32a) added 20 drops of liq Br and the mixt a.lIowed to
L.M~dar~ MAF 28, 480( 1954) (Some thermochemical stand for ca 30mins. After removing AcOH and the
data) 33)G.Desseigne & J. Trenchant, CR 239, excess Bi by bubbling with air, the residue is
769-71(1954) & CA 49, l1285(1955)(Influence of dissolved by heating in 20ml ethanol and, while
certain groups in substituted ureas, such as the soln is boiling, cold water is added in small
Centralizes, on their geIatiniz.ing power for NC) portions until a small amt of permanent residue
34)J. Vaganay& S. Wevert, FrP 1058486(1954) /2 is formed. After cooling the mixt, some of the wh
MP 37, 525-8 (1955 )(Improvement in prepn of trysts are collected, dried and tested in Fischer
Centr 1 and of other symmetrical dialkyldiary- (or equivalent) melting point apparatus (mp of
Iureas) 35)M.ParpaiIlon, MP 38, 233-41(1956) & dibromocentralite is 123.0-1 23.5°)
CA 51, 11717(1957){ Formation of comple~NHa ~ Centrality 1, intended for use in US
EtCentr-NGu, OC [N(C2H5).C=HS ] ~-HN:C military propInts(Ref 36) shalI be supplied in
~NHeNO. the form of either white lumps(CIass 1), powder
36) R. R. Buell, USP 2843584(1958) & CA 52, 4 (Class 2) or flakes(Class 3), consisting essentia]IY
 C 130

of diethyldiphenylurea. All classes shall be free washings of fUMeI, the mixt is titrated with N/10
from grit or visible impurities and meet the NaOH soln in presence of phpht indicator. A
folIowing other requirements: blank detn, using the same ingredients as above
I) Solidi/icatiorz point -71° to 72.5° incl and the except Cent, is run simultaneously
substance shall melt to a bright clear liquid, %Ethylaniline = [ 12. 1(V, - V2)N] /W, where
free from scum and deposit. Test shall be v, = ml of NaOH soln required for blank; V2= ml of
conducted in an apparatus similar to the one NaOH soln required for sample; N=normality of
described in Ref 36$p 313-R, except that the 2nd NaOH soln and W=wt of sample
thermometer is provided for correction: The inner b) Tertiary amines, A 5g sample in 20ml of benz
tube, filled to within 11~” of the top with molten contained in a separatoty funnel is thoroughly
Cent, is inserted in the larger tube, which in turn shaken with 20ml of N/2 HC1 and then allowed to
is pIaced in a large mouth bottle, 100ml capacity, rtand for few reins. The separated aq layer is
filled to within 1” of the top with water at 650., transferred to a 50ml Nessler tube ro which are
The 1st thermometet(standard) is adjusted so that also added distd w washings of funnel and 2 ml
the bulb is in the center of molten material, of N NaN02 soln. Then the contents of tube are
while the bulb of the 2nd therm is in the air space made up to 50ml mark and, after thorough
above it and in the mid point of the exposed Hg shaking, allowed to srand for 30min. By means of
column of the 1st thermometer. The molten a calorimeter the color is compared with standards
material is stirred vigorously by up and down contg known arnts of diethylaniline
movemtnts of hand stirrer until solidification V) Acidity - shall not exceed lml of N/10 NaOH
begins and the temp stops failing. Then the temp soln per 100g of Centr. A 10g sample is melted in
will start to rise and is observed carefully until 30ml of hot distd w contained in a flask and the
the maximum is reached. This temp is recorded as mixt is shaken vigorously until Centr crystallizes.
the uncorrected solidification point(T). This max After cooling the mixt to RT, it is titrated with
temp is corrected for emergent stem by adding N/10 NaOH in presence of phpht indlcatot. At
the value calcd from the formula: N(T-t) x 0.000159, the same time the vol of N/10 NaOH required for
where N=degrees in the exposed mercury column, a blank is detd and this is deducted from vol
T uncorrected solidification point, t= av temp of required for the sample. The corrected reading
the exposed Hg column detd by means of the 2nd shall not exceed O. lml of N/10 NaOH for 10g
thermometer and 0.000159 = coefficient of expan- sample
sion of Hg in glass VI) Hydrolyzable chlorine Compounds - shall be
II) Volatile Mutter - 0.1%, maximum. It is detd by absent. A 5g sample contained in a beaker is
heating a 5g sample in a tared shallow dish, for warmed on a water-bath for 15mins with 10ml of
2hrs at 600, cooling in a desicator and weighing 5% Na ethylate soln in ale, then diluted with
III)A.sb Content - 0.3% max. It is detd by placing cold distd w, allowing Centr 1 to crystallize. The
a 5g sample in a tared crucible, adding alcohol slurry is filtered, the filtrate acidified with coned
to completely cover the sample and igniting the HN03 and tested for chlorine ion by adding 5ml
mixt. After completion of combustion, the crucible of 10~ AgN03 soln, The opalescence shall not be
is heated to redness until alI carbon has been greater than that produced by a reagent blank
removed, cooled in a desiccator and weighed VII) Particle Size. Class 2(powdet) - a minimum
IV)S econa’ary and Tertia~ A mines. The sum, 99.9% of the material shall pass thru a US Std
calcd as ethylaniline and diethylaniline, No 30 sieve; Class 3( flakes) - a min 99.9% shall
respectively, shall not exceed 0.20% pass thtu No 3% sieve; the average of the max
a)secondary amineso A 25g sample~ dissolved in thickness of 25 flakes, as detd by micrometer,
30ml of benz contained in an Erlen fI is treated shall not exceed 0.025”. The screen test is
with 5ml of N/4 soln of Acz O in xylene and, conducted by placing a 100g sample on the
after scoppering the flask, allowed to stand required screen provided with a bottom pan and a
overnight, Then 25ml of N/10 Na OH soln is cover and shaking either by hand(for Iomins) or
added and, after thorough shaking, the mixt is for 5 reins by means of a mechanical shaker
transferred to a separator funnel and to this are geared to produce 300 ~ 15 gyrations and 150 ~ 10
added distd w washings of the flask. After adding taps of the striker per min(Comparison of US Std
2.5mJ of N/10 HCI, the funnel is shaken and Sieves with Tyler, Brit & Ger series is given in
allowed to stand. The separated aqueous layer is Ref 35, Table l,p A674)
transferred to a beaker and, after adding distd w
 C 131

Determination of Centralite 1 in Propellants

A. Volumetric Bromination Method(For detn of in the proplnt is less than 4%, the soln is
Centrl innewlymanufd single- or double-base transferred to a 250ml iodine titration flask, Then
proplnts contgno other brominatable materials, the extraction fIask is rinsed with four 10ml
such as DPhA, acardites, urethanes, p-nitro- portions of glac A cOH txansf erring the rinsings to
methylaniline and salicylates). This method, the iodine flask, After cooling the soln to
described in Ref 34 as Method 202.2.2, consists 20° ~ 2°, exactly 25ml of N/5 std bromate-bromide
of the following operations: soln is added
a) Preparation of Sample. If the proplnt consists Note: This soln is prepd by dissolving in distd w
of grains weighing 0.2g or less, it is carefully 5.6g of KBrOa dried at 100° & 30g of KBr and
ground, few grains at a time to pass a 10-mesh diluting the soln to 1 liter with distd w(see Method
screen. A laboratory mili, such as Wiley, Model 605.1 of Ref 34). It is standardized with N/10 Na
No 2G(provided with a shield and an explosion l thiosulfate soln which is prepd by dissolving 26g
-proof moto~) is used for this purpose(see Ref 34, of pure Na2S203. 5H20 & O. lg of Na2C03 in
Method 509.3. 1). The ground sample is placed sufficient smt of distd w to make I liter and
immediately in a bottle with ground-glass stopper. standardizing it, after allowing to stand for at
‘For larger than O. 2g grains, they are sliced by least 24hrs, with K2Crz07 soln in presence of
means of “powder cutter” with beryllium alloy KI & HcI as described in Method 602.1 of Ref 34
blade, to pieces ca 0.17mm thin and these are Then the stopper of the flask is moistened
cut into pieces ca 1/8” square prior to grinding with one drop of 15% KI soln, 5mI of 3$% HC1
them in the laboratory mill, as above. In case of sohr is added to the flask and exact time is
sheet proplnt; it is cut into pieces ca 1/8” square noted, The flask is stoppered immediately and
using beryllium alloy shears, and the cut pieces swirled for few seconds to allow the bromination
are placed immediately in a bottle provided with a to proceed. After elapse of 1,0~ 0,25 reins from the
glass stopper. Before grinding the pieces in the time of addn of HCI, the stopper is removed, l(lml
mill, they are made brittle by chilling them. For of 15% KI soln is added and the flask swirled.
this, the bottle is placed in an ice-salt bath until Then the gutter and walls of the flask are rinsed
the grains become brittle(Ref 34, Method 509.3. I) with distd w and the contents is titrated
b) Extraction o/ Sample. A 5g sample(weighed to immediately with ‘O. I N std Na thiosulfate soln
within 0.2mg), of ground proplnt ,is transferred to until the appearance of light yellow color.
an extraction thimble which is placed in an Finally, 5 ml of starch indicator soln is added
extractor(such as Soxhlet or Wiley), provided with and titration continued until the blue color of
a condenser( such as Allihn type) and an extraction soln disappears
flask. After filling the flask to about half with Note: .Starch indicator soln is prepd by dissolving
anhydtous methylene chloride, CH2 :C12(US 2g of soluble starch and 1-2 milligrams of
MiIitary Spec MIL-Dw5998)(See Note below), the Hg12(as preservative) in a small amt of cold distd
apparatus is assembled and the flask is heated on w) pouring the soln slowly, with stirring, into
a hot plate, adjusting the temp so that the solvent 500ml of boiling, freshly distd w and continuing
drips from the condenser to the thimble at the rate to boil for 5mins(See Method 701.1 in Ref 34)
of 2-3 drops per second. The operation is A blank is run simultaneously with sample,
continued until the extraction is completed. This using 50ml of glac ACOH & 25ml of 0.2N bromate
can be verified by testing calorimetrically (see at -bromide soln. The percent of Centr 1 is calcd
the beginning of this analytical section) the liquid from the following formula: [6.71 (A-B)N] /W,
dripping from the thimble, When the extraction is or in case of Centr 2(Methylcentralite):
complete, the solvent is evap, using a stream of [6. O1(A-B)N] /W,where A=ml of Na thiosulfate
dry air and the dry residue is retained for further soln required for the blank; B = ml of thiosulfate
tests(Ref 34, Method 104. 1.3) soln required to titrate liberated iodine in the soln
Note: Methylene chloride is used as extraction contg the brominated sample; N=normality of
solvent (in preference to ether or CC14) because thiosulfate soln and W=weight of sample corrected
it has, a low solvent effect on NC and is safe to for total volatifes
handle Note: If the Centr 1 content of the proplnt is
c) Determination o/ Centraiite 1 in Extracted expected to be betw 4 & 6%, the contents of
Matedal, The dry residue in extraction flask is extraction flask is dissolved in loml of gIac
dissolved in 10ml of glacial AcOH(US Spec AcOH [See opn (c)] and transferred to a 100ml
JAN-A-465) and, if the nomin~ content of Centr volumetric fIask. After rinsing the extraction
 C 132

flask with four l(lmI portions of gIac ACOH and connected, the receiver is removed, 5g of Na
transferring the rinsings to a vol flask, its chloride is added to the distillate and it is
content is made up to 100ml mark with glac AcOH. transferred to a 1 liter separator funnel. The
Then 50 ml is pipetted into iodine flask and used condenser, the goose-neck tube and adapter are
for bromination as described in opn c. If more rinsed with ca 60ml of ether and the tinsings
than 6% of Centr I is expected to be in the are transferred to the separatoty funnel
proplnt, only 25ml of soht in volumetric flask is c) Extraction. The funnel is stoppered, shaken
transferred to iodine flask and to this is addbd vigorously for several reins and the aqueous
25ml of glac AcOH before the bromination procedure layer is drawn off into the 750-ml receiver
B, Bromination Method [ For detn of available flask, whereas the ether extract is transferred
stabili zer(Centr 1 & DPh A) in aged proplnts contg to a 200ml volumetric flask. The aq layer is
no other brominatable materials, such as acardites, transferred back the the separator funnel for
urethanes, phenols, p-nitromethylani line and the 2nd extraction with 60ml ether. This
sslicylates). Accdg to Apatoff & Cohen(Ref 37), extract is also transferred to the 200ml vol
the US Military .Standatd Method 217,2.1 known as flask and the aq Iayer to the separator funnel.
“Available Stabilizer and desctibed in Ref 34, After the 3rd extraction, the contents of the
depends on soly of dibromoethylcentralite in 200ml flask is made up to the mark with ether
hot 47. s% alcohol as a means of separating it d)Determination of DPhA by Gravimetric
from tetrabromodiphenyl amine ppt. After diluting Bromination, One half(100m1) of the above ether
the filtrate with w and heating the soln for extract is pipetted into a 250a-11beaker, while
several hrs on a water-bath(while a stream of air the other half is reserved for opn (e) which
is directed on the surface of liq to assist the follows, After placing the beaker on a closed
evapn), the dibrotnocentralite precipitates and water-bath, bromine is added drop by drop untiI
is filtered off & weighed. It has been found a slight excess(which is indicated by appearance
difficult to obtain quantitative recovery of Centr of light reddish-brown color) is present(ca 0.6ml
by this method because of failure of the dissolved is required for each percent of Centr & DPhA).
Centr 1 to completely precipitate and coagulate Then the beaker is swirled, the soln is aIIowed
during heating on the water bath. It appears also to come to a boil and the beaker is immediately
that the concn of alc(47. 5%) and temp of soln are removed from the top of the bath. The rest of the
critical in Method 2.17.2.1 ether is evapd by a current of dry air just to
In view of the inadequacy of the above disappearance of ether odor, because prolonged
methodi Alpatoff & Cohen developed at the lab of evapn after removal of ether will yield low
Frankford Arsn, the following method, which is results. The residue in the beaker is heated to
claimed to be rapid and accurate: boiling with 40ml of 95z alc and the exact time
a) Preparation 0{ Sample. Same as in opn(a) of is noted. Then, 40ml of dist w is added and the
(A) beaker is allowed to remain on the bath for
b)D instillation. A 5g( weighed to within O. 2mg) exactly 10mins from the time noted, after which
sample of ground proplnt is transferred to a l-i the hot soln is filtered thru a tared 30ml fritted
balloon flask, and, after adding 100mI of distd w & glass crucible of medium porosity. The ppt on
100ml of 30% NaOH solrI, the flask is closed witha the crucible consi sting of tetrabromo-DPhA is
two-hole stopper, provided with a stream inlet washed, first with ca 50ml of boiling 47.5% ale,
tube and a goose-neck tube ca 20cm high & llmm and then with distd w. This is followed by
OD. The latter tube is connected to condenser, &ying at 105 j 2° for 1 hr, cooling in a desicator
which is provided at the other end with an and weighting. These opns are repeated until the
adapter inserted in a 751)-ml Erlen fl (receiver) wt between weighings at 2hr interval is less than
contg 25m1 of distd w. After connecting the 0.5mg
inlet tube of the flask to a steam generator(either The % of DPhA is calcd from the formula:
a 2-1 balloon steam generating flask or a low (34.90 x A x 2)/Wr, where A=increase in wt of
-pressure steam line), the distn is conducted crucible and W=wt of sample, corrected for tota[
(without use of allxiliary heating of the flask contg voIatiles
proplnt) until, (in case of proplnts contg 4-5% of e)Determination of Total Volume of Sodium
Centr or 1-3% of DPhA), 450-500 mI of Iiquid Thiosulfate Equivalent. The remaining 100ml of
is collected. Then the steam generator is dis- ether extract [ see opn (d)] is transferred to a
250ml beaker, followed by rinsing the flask with
 C 133

a few inls of ether. After evapg the ether [ which 361 ,400( 1931)(An improved Taliani test for dem
could be done concurrently with rh e brominated of stabilizing action of various substances
portion of opn (d)] , the residue is di ssoIved in including Centr 1) 4)H.Levenson, I13C, AnalEd
glac AcOH, and the soln is transferred quantitative- 2, 246-7( 1930) [ Detn of Centr I in double-base
ly to a 100mI vol flask. Then the beaker is rinsed proplnts by extracting it(together with NG) with
with several portions of A cOH and the rinsing ether, evaporating the ether, dissolving the
added to the contents in the flask The fiask is extracted material in alcohol and treating the
fiIled to the mark with AcOH and, after mixing, soln with s td bromine- bromate s oIn in presence
exactly 50ml of soIn is transferred to a 250ml of HCI? 5)c).C. Ellington & H. B. Beard, JACI
iodine titration flask, an~ after cooling the soln 50, 151T(1931) & CA 25, 3485(193 I)(Modification
to 20 ~ 2°, 25ml of std 0.2N bromate-bromine soln of L evenson’s method: purified CC14 is used as
is added. Further procedure is the same as in solvent instead of alcohol; the advanrage results
opn (c) of A, but calcn is different, because here from the fact fhat CCla is non-reactive to bromine)
is detd the vaIue C, which is the mls of normal 6)Marshall 3(1932), 219( Color reactions for
Na thiosulfate soln equivalent to the sum of products from Centr I during aging of double-base
brominated stabilizers. It is equal to (A-B) x N x 4, proplnts) 7)0. Turek, Voj ensko-TechnickeZpravy
where A=ml of Na thiosulfate required for (Prague) 9, 73-5 & 96(1932); CA 26, 4953(1932)
blank; B=ml of Na thiosulfate required to (Modification of bromometric method of detn of
titrate the liberated iodine in the soln contg the Centr 1 and critical review of methods of
brominated sample and N=normality of Na Levenson and Ellington & Beard) 7a)K.Masaki,
thiosulfate soln BulIChemSocJapan 7, 353-62(1932) & CA 27
Centr 1 is calcd by converting the % of 904(1933)(A spectrochemical study of reaction
DPhA detd in opn (d) of (A) to its equivalent products betw Centr and gaseous N02) 8)M.
volume of normal Na thiosulfate soln and Tonegutti, SS 32, 300-5(1937)& CA 32, 1099
subtracting this value from the vol of normal Na ( 1938)(Detn of stability of smokeless proplnrs
thiosulfate soln equivalent to the sum of the contg Centr 1, DPhA or Acardite by methods of
brcminated stabilizers as obtained in opn (e) of Taliani and of Thomas. The Thomas method was
(B). If D(mls of normal Na thiosulfate soln found to be more reliable) 9) W.H. Brown,
equivalent to DPhA in sample) is equal to: SocChemIndVictoria, Proc 38, 42-6(1938) & CA
(%DphAx W)/2*115, hen % Centr I is equal tO 33, 6597( 1939)( Volumetric bromination method
[ 6.71( C-D)] /w, where C=ml of normal Na of dem of Centr 1; the procedure is similar to
thiosulfate soln equivalent to the sum of the that of Ellington & Beard) 10) Thorpe 4(1940),
stabilizers in sample and W=wt of sample corrected 52 I(A brief description of procedure for dem of
for total volatiles Centr in proplnts developed by Levenson)(See
Note:If instead of Centr 1, Centr 2(Methyl- Ref 4)(A1s0 estimation of nitrosamine present
centralite) is a component of the proplnt, the in aged proplnts) ll)R. B. Corey et al, OSRD
cal cn would be: Rept 1103(1942) and 1558( 1943)( Spectro-
%Centr 2= [6.oI(c-D)I /W photometric investigations of double-base propInts
Swedish requirements and test for Centr 1 contg Centr I) 12)Kast-Metz( 1944), 167
are given in Ref 33a* They include: appearance [Calorimetric reactions for deteding Centr I
solidification pt(72°), boiling pt(326°)~ matter and other tetrasubstituted ureas, such as Centr 2.
insol in ether-ale, ash, moisture and reaction A rose-red coloration is produced when a very
(whether acidic or alkaline) dil(l: 100) soht in coned H2S04 is treated with a
(Analytical procedures were reviewed by Mr few grains of powdered K2Cr207 or Pb02(Tafel
N. Liszt of PicArsn) Reaction). An intense red coloration is obtained
R e/s: l) J. Tafel, Ber 25, 412-13(1892)(Color when Centr is treated with a very small quantity
reaction for deteccion of Centr 1; rose-red color of K or Na nitrite in H2S04 soln(Desvergnes
is produced when a few trysts of K2Cr207 are Reaction)] 13)Kast-Metz(1944), 271-2( Qualitative
added to a smaIl sample dissolved in coned detn of Centr 1 in proplnts); 289-95 (Quantitative
H2S04) 2)H.L~corch~ & P. Jovinet, MP 23, detn of Centr 1 in propInts); 328-30(Dem of Centr
69-78 (1928)(A rather complicated and tedious I in Celluloid) 14)L.Pauling et al, OSRD Rept
method of quantitative detn of Centr 1 when in 4820(1945) [A modified volumetric bromination
mixts with NG) 3)J .Goujon, MAF 8, 837-902(1929) procedure which employs glac AcOH as the
& its Ger translation in SS 26,217,261,,289,330, organic solvent for the sample to be brominated,
 C 134

and combines the advantges of CC14 & alcohol & NG from NGu type of proplnts, such as Cordite
procedures(See Refs 4 & 5) in that the reaction -N; NGu is much less sol in this mixt than in
is carried out in a one-phase system which is methylene chloride alone) 28)J. Grodzinski,
inert to bromine] 15)L.P auling et al, OSRD BullResearch-CouncilIsrael 7A, 21-8(1957) &
Rept 5967(1945), 16( Spectrophotometric data for CA 52, 7020-1( 1958)(Colorimetric dem of
Centr 1 and its transformation products formed Centr in proplnts by means of eerie molybdate
during aging of double-base proplnts) 16)T.D. Soln) 29) M. Laccetti et al, GenLabRept
Waugh et al, IEC, AnalEd 18, 636-7(1946) 57-HI-519, PicArsn, Dover, NJ( 1957)( Development
(Improved volumetric-bromination for detg Centr 1 of spectrophotometric method for simultaneous
in smokeless proplnts. Methylene chloride is detn of “actual” Centr 1 and its primary
used to extract the stabilizer from proplnt and degradation products in aged proplnts) 30)L.
glac AcOH as the solvent in bromination) 17)Coll, Marvillet, MP 40, 273-87(1958) & CA 54, 25825
“Summary Technical Report of Division 8, NDRC~’ J 1960)( ChromatograPhic detn of Centr 1 and of
Vol 1, Washington, D~1946), 124-5(A brief other ingredients of proplnts) 31) M. A. Laccetti &
description of bromination procedures using M. Roth; JANAF*P ACSP Second Cooperative Test
CC14 and alcohol as solvent for tie extract) 18) Program on Stabilizers, PicArsnTechMemo No
S. Weisberger, PATR 1662( 1947) [Development GL,-6.59(1959)( Evaluation of methods for the
of chromatographic method for Jetg Centr in the analysis of DPhA, EtCentr and some of their
81mm mortar propint contg NC(13.25% N) 52.15, degradation products) 32)M.Laccetti, FREL
NG 43.00, DE@h 3.00, K sulfate 1.25 & EtCentr TechMemo No ACS.2-59, PicArsn, Dover, NJ(1959)
0.60%] 19) A. M. Soldate & R. M. Noyes, AnalChem (Spectrophotometric method for the detn of
19, 442-4(1947)(X-ray diffraction spectra for Centr admixtures of DPhA & EtCentr in proplnts) 33)
1) 20)1. S. Hirschhorn, AnalChem 19, 880-2(1947) M.Roth et al, FREL TechMemo No ACS-2.60,
[Rapid method of detn of Centr 1 & NG in rocket ( 1960)( Interlaboratory detn of specttophotomettic
proplnts. Both ingredients are extracted with 84% factors for DPhA & Centr 1 and their primary
ACOH and then Centr is detd by bromination degradation products) 33a) Anon, “Analytical
method of Waugh et al(See Ref 16)] 20a) T.C.J. Methods for Powders and Explosives”, AB
Ovenston & C. A.Parker, JSCI 66, 394-5(1947) Bofors, Nobelkrut, Sweden( 1960), 80-1 34)
(Detn of nitrosamine content of proplnts stabilized US Military Standard MIL=STD=286A(1961)
with Centr 1) 21) F. Pristera, PATR 1691(1948) (Propellants, Solid: Sampling, Examination and
[Modification of chromatographic method Testing); Method 202.2 .2(Detn of EtCentr in
described in PATR 1662( See Ref 18) to be applied newly manufd proplnts); Method 2 17.2.l(Dem of
to proplnts contg K nitrate instead of K sulfate] available stabilizer in aged proplnts) 35)PATR
22) T.C.J.Ovenston, JSCI 68, 54-9(1949) & CA 2700 VO1 1(196o), pp A516 & A674 36)US Joint
43, 5593( 1949)( Chromatography in an explosives Army-Navy Specification JAN-E-255 [Ethyl
laboratory) 23) T.C.J .Ovenston, Arudyst 74, Central ite(Carbamite)] 37)J .Apatoff & J. Cohen,
344-5 1(1949) & CA 43, 8137(1949)(Chron~ato- ‘ ‘Determination of Admixture of Diphenylsmine
graphic detn of Centr 1 in proplnts) 24)W.A. and Ethyl Centrality in Propellants” ,Test Report
Schroeder et al, IEC 42, 539-46(1950) T62-1 5-1, Ftankford Arsenal, Philadelphia, Pa
(Chromatographic-spectrographic method for detn (1962)
of compds formed during accelerated aging of Centrality 1; Nitro Derivatives
double-base proplnts contg Centr l; color Mononitrocentralites, Cl ,Hl #303; mw 313.35,
reactions with eerie sulfate reagent) [See also N 13.42%. Two isomers are known: 2- Nilrocen-
IEC 41, 2822(1949)] 25) V. R. Grassie et al, trulite, CO1 crysts(from benz-ligroin), mp 56-7°;
CanJRes 286, 468-84(1950) & CA 45, 3594(1951) was prepd in small yield by condensation of
(Preliminary tests on possible new stabilizers N-ethyl- 2-nitrocarbanilyl chloride with N-e~ylani-
for NC, as compared with standard stabilizers, line(Refs 7 & 8) and 4nitrocentndite, .yel,
such as Centr 1) 26)G.Sifre, MP 35, 382-6 viscous oil which could not be induced to
(1953) & CA 49, 9448( 1955)( polarographic detn crystallize; was prepd by condensation of N-ethyl
of Centr 1 in propInts; the method is fairly rapid, -4-nitrocarbanilyl chloride with N-ethylaniline
but precision is no better than 2%) 27) J. O. Watts (Refs 7 & 8)
& H..StalcuP, AnalChem 29, 253-4(1957) & CA 51, Ldcorch~ & Jovinet(Ref 5), by nitrating
5424( 1957) [An azeotropic mixt of pentane & Centr l(dissolved in AcOH) with 1 mole nitric
methylene chloride(2: 1) is used to extract Centr 1 acid prepd a product, melting at 43° which was

— —
 C 135

probably an impure nitrocentralite; it was not One of the most important investigations
properly identified of transformation products of Centr I, formed
Dinitrocentralites, Ct ,Ht *N40~; mw 358.35, during aging of some doubIe-base proplnts, was
N 15.64%. One isomer: 4, 4’-Dinitrocentralite, con~ucted during WWII and CALTECH under
OC [N(C2H5)C6H (NOZ)] z, bright yel c~sts direction of Dr L. PauIing(Ref 4). Abstract of
(from ale), mp 147%(by Maquenne block); was this work is given in Ref 5 and an abbreviated
prepd by nitrating Centr I with coned nitric or version in R ef 9. Some of the transformation
with mixed nitric-sulfuric acids(Refs 1,2,3,4 & 6). products were synthesized, as described in
A product melting at 144° was prepd by treating Ref 8. The work on transformation products of
Centr 1 with nitrous fumes(Refs l,P 181) Centr I done at PicArsn is briefly described
Trinitrocentralites, C,7Hj7N507, mw 403.35, in Refs 10 & ll(See also Centrality 1, Analytical
N 17.36%. One isomer, presumably: 2,4,4’ Procedures)
- Trinitrocerztralite, crysts(from absol ale), mp Following is a brief description of the
151.5-152.3°, was prepd by nitrating 4,4’ work done in the US during WWII:
-dinitrocentralite with mixed nitric-sulfuric acid, TWO double-base proplnts were
as described in Ref 7,p 948 investigated, one was Cordite jP 76, a
Tetranitrocentralites, C, ~H1 ~N60$; mw 448.35, “solvent” process compn of high content of
N 18.75%. One isomer: 2,4, 2’4’. Tetranitro- Centr, Its approx compn was: NC(12. 24% N)
centr~ite, OC [N(CZH5).C6H3(N02 )21 ~, cqsts, 49.6, NG 41.4 & EtCentr 9%. The other,
mp 178°(by Maquenne block) is known. It can RPL ~42(Radford Pilot Lot No 142), was a
be prepd by nitrating Certtr 1 with fuming nitric c‘solventless” process compn conrg a small amt
or with coned mixed nitric-sulfuric acid(Refs 1,2 of Centr. It compn was: NC(13.22% N) 59.0, NG
& 6). A small quantity of tetranitro compd was 40.0 & EtCentr 1%. Artificial aging of these
reported to have been obtained on treating Centr proplnts was produced by heating samples in
1 with nitrous fumes(Ref 3) vented metal cans at 65° & 75° for varying
Hexanitrocentralites, Cl ,Hl ~N@Ot ~; mw 538.35, periods of time up to 2yrs. The samples were
N 20.82%. One isomer: 2,4,6,2’,4’,6’ Hexanitro” periodically removed, cut into slices 0.1 to O. 15mm
cerztraZite, oc [ N (CzH5). CeHz(NOz)a ] z, trysts, in thickness by means of a sliding microtome,
mp 248°(by Maquenne block) is known. It was weighed and extracted for 2-3hrs with anhyd
prepd by nitrating Centr with coned nitric acid ether or methylene chloride in a Soxhlet
and oleum as described in Ref 4. Its soly in grams apparatus, Extracts in ether were first evapd
per 100g of solvent at 25.5° is: EtOAc 0.839, to remove the solvent(because it is a strong
Me2C0 I. 055, absol EtOH 0.029, MeOH 0.067, eluent) and the residue was taken up in
C6 H6 0.054, CHC13 0.339, Et20 0.024, CS2 I: I benz-ligroin. Extracts in methylene chloride
0.007, CC14 0.028, C7Ha 0.031 & C5H~N 12.65 were either diluted directly with Iigroin or
(with decompn). Its expl props were not detd partly concentrated and then diluted with ligroin.
Accdg to Thorpe(Ref 6), nitration of Centr Aliquot portions of the resulting solns were
I did not produce Hexanitrocentralite taken for chromatography. The absorbent used
Re/s: l)Beil 12, [238] 2) M.Giua 8: G.Guast~la~ in all of the chromatographic experiments was a
AttiAccadTor 60, 75(1925) & CA 19, 2133(1925) 2:1 mixt of silicic acid(Merck Reagent) and
3)A.Apard, MP 22, 181-2 & 187-9(1926) 4)L. Celite 535(of Johns ManvilIe Corp). The apparatus
Desvergnes RevChimInd 37, 41(1928) & CA 22, was the same as for detn of transformation
1963(1928) 5)H.L6corch~ & EJovinet, Mp 23, products of DPhA described by W.A.Schroeder
148-9(1928) 6)Thorpe 4(1940), 521 7) P. E. Wilcox, et al, IEC 41, 2818(1949). The quantity of each
& W. A. Schroeder, JOC 15, 946-8(1950) 8)W.A. compd isolated on chromatographic column
Schroeder et al, IEC 42, 545(1950) was estimated spectrophotometrically in
Centralite 1; Transformation Products Formed absolute alc by measuring the optical density
During Aging of Propellants Containing It. at the wave length of maximum absoprtion(Refs
Aging of proplnts contg Centr 1, its stabilizing 4&9)
action on NC & NG, md transfo~ation products Quantitative analyses were made on
formed during aging are discussed in Refs 1-7 & samples which originally contained ca 100mg of
9-10. Nitro compds of Centr 1, some of them Centr. The chromatography c-spectrographic
formed during aging of proplnts, are described method can detect quantitatively less than O.lmg
here under Centrality 1, Nitro Derivatives of of substance
 C 136

When the chromatographic method was Transformation products of Centr 1

applied to selected samples of each proplnt, it isolated at PicArsn(Refs 10 & 11) from stored
was possible to isolate about 40 compds, of double-base proplnts included: nitro- and
which 17 were definitely identified, 3 nitroso- derivs of Centr and products formed
tentatively identified and the remainder could on its cleavage by acids. These included
not The compds identified could be classified N-ethylaniline which, being very reactive, com-
as follows: bined immediately with nitrous acid to form N
a) Compounds in which the urea structure is -nitroso-N-ethy laniline which was present in
still present. These included: 4-nitro-, 4,4’-dinitre- large amt. This product was removed together
and only small amts of 2,4,4’-trinitro- and 2-nitro- with 2-nitro-N-ethyl ~iline from degradation
ethylcarbanilides products by steam distn. Some derivs of Centr I
b) Compounds in which the urea structure is isolated from aged proplnts possessed stabi.
split. These included N-nitroso-N-ethy Ianiline lizing props
& 4-nitro-N-nitroso-N-ethy laniline and traces of (The section on Transformation Products
4-nitro-N-ethylaniline, 2-nitro-N-ethylaniline, was reviewed by Mr. N. Liszt of PicArsn)
2,4-dinitro-N-ethy laniline, N-ethylcarbanilide, Re/s: l)H.L6corch4 & P. Jovinet, MP 23, 69 &
4-nitroaniline & 4-nitrophenoL Certain other 147(1928); CA 22, 3779(1928) & 23, 2296(1929)
identified compds, such as 4-nitro-N,N-diethyl- {Transformation products of Centr 1 formed in
aniline, probably were derived from traces of double-base propInt [ containing NC(12% N) 66,
N, N-diethylanil ine which could be detected in NG 27 & Centr ~%] after 4yrs of storage at 50*,
commercial Centr 1 consisted mostly of p-nitrophenylethy lnitrosamine
c)Compounds tentatively identified. These were and mononitrocentralite. The 1st was volatile
probably degradation products of NG, because with steam while the 2nd was not } 2) Marshall
they resembled some of the substances isolated 3(1932), 211-12 [ Centr 1 in a proplnt stored at
from old solns of NG RT’s or above, gradually becomes hydrolyzed,
Besides the identified products, there yielding C02 and N-ethylaniline, the latter
were isolated several transformation products, gives a slightly basic reaction and can
the structure of which were not detd. Another neutralize any acid present. Ethylani line can
undetermined problem was the fate of portion also combine with No to form ethylphenyl.
of Centr l(ca 50%) which was apparently depleted nitrosamine, H5C2.N(NO).C6H5, which is
from the proplnts and could not be accounted further converted into nitronitrosamine and
for in terms of Centr derivs in the extract into nitroethylph enYlamines.Some nitrocentralites
Behaviors of proplnts Jp 76 & RPL 142 are also formed. As only a small quantity of
0 n heating at 65° were not identical, Although N-ethylaniline is present at any one time, it
the heating of samples of JP 76 continued for does not seriously attack the nitric esters and
107 weeks, no blistering or evolution of N02 Centr I can therefore be used in proplnts contg
was observed. On the other hand, samples of NG] 3) Thorpe 4(1940), 521 [Stabilizing action
RPL 142 became blistered and evolved N02 of Centr I is explained by the theory that as
after 93 weeks of heating. While in JP 76, soon as the proplnt contg NC-N G-Centr 1 becomes
N-nitroso-N-ethy laniline was the major primary aciic, the Cent is hydrolyzed to ethylaniline
transformation product of Centr I and 4nitro- which reacts with any nitrous acid present to
centralite was the minor product, the situation form phenylethylnitrosamine. Any nitric acid
was reversed in RPL 142, where 4-nitrocentralite formed during the decompn of the proplnt is
predominated. Furthermore, the rate at which absorbed(at least partly) by Centr with the
Centr 1 disappeared from JP 76 was about 5 formation of a mononitrocentralite. By estimating
times as great as that at which it was depleted the amt of nitrosamine present it is possible to
from RPL 142. This was due to the greater estimate approximately the extent of c~aging~ $
initial amt of Centr in JP 76 of a proplnt. For this detn 2g of the finely
Only three samples of RPL 142 proplnt divided proplnt can be digested for 24hrs at RT
were heated at 75° and, of these, two became with looml of ale, 2ml of sohr placed in a test
blistered and evolved NO= after 33 week% while tube, 5ml of alc added, followed by lml of a 1%
the 3rd sample remained unchanged(except for soln of ct-naphthylamine & 5 drops of HC1. The
color) even after 41 weeks of heating(Refs 4,5, closed tube is then placed in a water bath,
6&9) heated to 600 and, after 10mins the color of

1 ——.
 C 137

liquid is compared with a standard] 4)L. under Analytical Procedures)

P~uling et al, OSRD Rept 5967( 1945)( Trans- Centr 2 was first prepd by Michler(Refs
formation products of Centr I during aging of 1 & 2) on passing phosgene thru boiling
various double-base proplnt”s) 5) C011, “Summary cJimethylaniline. Michler & Zimmermsnn(Refs
Technical Report of Division 8, NDRC~~ol 1, 1 & 3) prepd it by heating methylphenylcarbamyl
Washington, DC(1946)(Resumt! of OSRD 5967) chloride with methyl aniline & some Zn dust.
(See Ref 4) 6)C.A.Parker, JSCI 67$ 434-6(1948) Dains et al(Refs I & 4) prepd it by heating
(Chromatographic separation of some trans- equimolecular quantities of N-methyl-N, N’
formation products of Centr 1 formed during -diphenylthiourea with methylphenylcarbamyl
aging of Cordites. These products include chloride at 1500. Mailhe(Refs I &7) prepd it
N-nitroso-N-ethylaniline and its nitro derivs) by passing vapor of N-methylformanilide(yel,
7)A.G.Garcja-Guti~rrez, Ion(Madrid) 9, 165-7 viscous oil, bp 286°) over finely divided
(1949) & CA 43, @25( 1949)(A review of nickel at 380-400°
stabilization of smokeless proplnts and ma- Gelatinizing power of Centr 2 was
terials used for stabilizers. These included discussed by Davis(Refs 6 & 11) and its
Centr 1 and Centr 2. It was found that both stabilizing power was investigated by Rinken-
Centralizes form analogous transformation bach(Ref 12), Grassie et al(Ref 17) and
products in aged proplnts, except that nitration Desseigne & Tranchant(Ref 21)
of Centr 2 proceeds more easily and higher Uses: Centr 2 can be used for the same purpo-
nitro derivs can be formed) 8)P. E. Wilcox & ses as Centr l(Refs 6 & 22) but it is sometimes
W.A. Schroeder, JOC 15, 944-9 (1950 )(Synthesis not as desirable due to its rather high mp
and detn of props of some derivs of urea and (121-121.5°) and because it is not as good a
of Centr, which were formed during accelerated gelatinize for NC as Centr l(Ref 6). It was
aging of double-base PrOP~ntSO Among the used during WWI in some rifle proplnts(Ref 11),
compds prepd and investigated were mono-, di- and was proposed as an anti-knock additive to
and trinitto- centralizes. They are described motor fuels(Ref 14). It can also be used as a
here under Centrality 1, Nitro Derivatives) coating agent of proplnts(Ref 22)(See also
9)W.E.Schroeder et al, IEC 42, 539-46(1950) Cenrralite 2, Analytical Procedures; Centrality
(Transformation products of Centr 1 formed in 2, Nitro Derivatives of and Centrality 2
double-base proplnts during accelerated aging) Transformation Products Formed During Aging
10)M.Laccetti, GenLabRept 57-HI-519, PicArsn, of Propellants Containing It)
Dover, NJ(1958) 1 I)M.Roth et al, FREL Re/s.’ l)Beil 12, 418, (251) & [236] 2)w.
TechMemo ACS=2-60, PicArsn, Dover, NJ(1960) Michler, Ber 9, 716(1876) 3) W.Michler & R.
Zimmerman, Ber 12, 1166(1879) 4) F. B. Dains
Centralite 2 or Methylcentralite (US); MoUit 2 et al, JACS 38> 134(1916) 5)H.Kast~ “Spreng-
(Ger trade name for product used as a plasti- und Ziindstoffe”, Vieweg, Braunschweig(1921),
cizer); N, N’.Dimetbylcarbanilide or N, N’ 185(Some props of Centr 2) 6) T. L. Davis, IEC
.DimethyZ-N, N’-dipbenylurea, OC [N(CH3 )J- 14, 114( 1922) (Gelatinizing power of Centr 2 for
CeH5] z; mw 240.29, N 11.66%; ctysts(from NC in single-base proplnts is lower than that
ale), mp 121.5°, bp 350 °(Refs 1,13 & 15); of Centr 1 or Burylcentralite) 7)A.Mailhe, CR
difficultly volatile with steam(Ref 13); heat of 176, 904(1923) & JCS 124 I, 458(1923 )(New
combustion at const VOI, Q;, 808 lcal/g or method of prepn of Centr 2) 8)Stettbacher
1941.7kcal/mole & at const pressure, @, (1933), 197(Cenm 2 & Centr 1 were investigated
8087cal/g or 1943. lkcal/mole; heat of formation in Germany ca 1907 as possible stabilizers for
at const vol, Q~ 66.5cal/g or 16. Okcal/mole & NC in smokeless proplnts) 9)T.Urbadski,
at const pressure, Q~, 89.4cal/g or 21. 5kcal/mole RoczChem 13, 399(1933) & 28, 27’(1943)(f3inav
(Refs 19 & 20); calorific constant, h, is -23.8 mixts of Centr 2 with expls, such as HNMnt &
cal per O.Olg of Centr 2, which corresponds to PETN have ,correspondingly, eutectic points
calcd calorific value at const pressure of of 77.4° & 102.7°) 10)Thorpe 4(1940), 521
1930kcal/mole at 17°, vs experimental value of (Some props of Centt 2) ll)Davis( 1943), 319
1948.5kcal/mole(Ref 16). Centr 2 is insol in W, (Centr 2 was widely used during WWI as a
SOI in alc(7g in 100ml of 96% alc at RT); sol in deterrent in rifle proplnts designed to produce
ether & benzene(Refs 1, 13 & 15). Its SOIY in very high velocities) 12)W.H.Rinkenbach,
100g NG is 13.Og at 18° & 19.4g at 23 °(Ref 8, PATR 1480(1944)(Investigation of various US
 C 138

single-base proplnts has shown that Centr 2 IV)Arnines -0. 20% calcd as methyl amine when
is as effective as DPhA in stabilizing FNH-M1 detd using the proced IV for secondary amines
proplnt, but not effective for FNH-M3 and Pyro described under Centr I but calcg % methyl-
proplnts. It is, however, a better stabilizer than aniline from the formula: [1O.7(V, -V2)N] /W
methyl acardite or carbazole) 13)Kast-Metz -A x 1.78, where V,= ml of NaOH soln required
( 1944), 165-6(Some props of Centr 2) 14)G.B. to titrate blank; V2. ml of NaOH soln required
Banks, USP 2373372(1945) & CA 39, 3423 to titrate sample; N.normality of NaOH soln;
( 1945)(Addn of small quantity, such as 0.1%, W=wt of sample and A=% acidity as AcOH
of Centr 2 to motor fuels improves their Note: This method is not specific for amines
antiknock properties) 15) P~rez Ara( 1945), 423 but will detect other groups such as OH
(Some props) 16) J. Taylor et al, JPhysCollChem V)Acidity - shall not exceed 0.006% acid calcd
51, 590(1947 )(Some thermochemical props) as AcOH. A 20g sample dissolved in lC)Oml of
17)V.R.Grassie et al, CanJRes 28B, 468(1950) benzene is extracted with three successive
& CA 45, 3594(195 l)(Comparison of stabilizing 25ml portions of boiled w and the combined
props of various stabilizers including Centr 2) extract titrated with 0.02N NaOH soln using
18)W.A.Schroeder et al, AnalChem 23, 1743 phpht as indicator. A blank detn is run con-
(1951)(uv & VisibIe spectra of Centr 2) 19)L. currently and % ACOH is calcd from the formula:
M6dard & M. Thomas, MP 34, 423-4 & 440(1952) [6.0(v1 -V2)N] /W, where VI =ml of NaOH soln
(Some thermochemical data) 20) L. M6dard, MAF required to titrate sample; V2. ml of NaOH soln
28, 480(1954 XSarne info as in Ref 19) 21)G. requited for blank; N=normality of NaOH ~oln
Desseigne & J. Trenchant, CR 239, 769(1954) and W=wt of sample
& CA 49, l1285(1955)(GeIatinizing power for VI)hydrolyzable Matter - shall be absent when
NC of Centr 2 in comparison with other sub- tested as described under Centr 1
stituted ureas and urethanes) 22)US Military VII)Particle Size. Class 2(powder)-a min of
Specification MIL=M-19719(1960),P 5 100% of the material shall pass thru US Std
No 50(297 micron) sieve c crrforming to US Spec
Centralite 2, Analytical Procedures. Calori- RR-s-366, The test is conducted in the same
metric & other qualitative tests for Centr 2 are manner as described for Centr 1
similar to those described under Central ite 1, Determination 0/ Centrality 2 in P70peUants
Analytical procedures(See also Refs 1, 2 & 3)* may be conducted as described in Methods A
Chromatographic detn is described in Ref 4 and and B under Centrality 1, Analytical Procedures,
analysis by IR spectroscopy in Ref 6. In Ref 5 except that the formulas for calcns are different
are given UV and visible absorption spectra of and are given under Centr 1
Centr 2 and in Ref 7 described detn of its UV Swedish requirements and tests are given
absorption spectra in Ref 8. They include: appearance, solidifica-
Centrality 2 intended for use in US tion pt(121°),boiling pt(350°), matter insol in
proplnts(Ref 9) shall be supplied either in the eth-ale, ash, moisture and reaction(whether
form of white lumps(Class 1) or powde4C~ass 2), acidic or alkaline)
consisting essentially of dimethyldipheny lurea. Re/s: l) B. T. Dewey & A. H. Gelman, IEC,
Both classes shall be free from grit or visible AnalEd 14, 361(1942) & CA 36, 3750(1942)
impurities and meet the following other (Color reactions of Centr 2 with H2Se03-H2S04
requirements: solns) 2)Kast-Metz( 1944), 167( Color reactions
1).$olidi/ication Point - 120.5° to 122°, and the for detection of Centr 2 are identical with those
substance shall melt to a bright, clear liquid described for Centr 1) 3) Kast-Metz( 1944), 292-3
free from scum and deposit. Test shall be (Gravimetric and volumetric methods for detn of
conducted in an apparatus and in the manner Centr 2 in proplnts are similar to those for Centr
similar to proced (1) described under Centrality 1) 4) T. C. J. Ovenston, Analyst 74, 344-51(1949)
1, Analytical Procedures, except that no water & CA 43, 8138-9( 1949)( Chromatographic in-
is placed in the outer bottle, just air vestigation of propints using various stabilizers,
II)VolatiZe Matter - 0.20% max. Same detn as fot among them Centr 2) 5)W. A. Schroeder et alt
Centr 1, except that heating shall be for 3hrs AnalChem 23, 1740-7(1951) & CA 46, 5434(1952)
at 100-105° (Detn of ultraviolet and visible absorption
III) Ash Content -0. 1% max. Same test as for spectra of several stabilizers, among them Centr
Centr 1 2, in ethanol) 6) F. Pristera, AnalChem 25, 844
 C 139

(1953) & CA 47, 9207( 1953)( Analysis by infrared N- Ethyl-N’ -met by LN. N’.dipbenylurea,
spectroscopy of propInts contg various stabilizers N(CZH5).C6H5
among them Centr 2) 7)P. G. Grammaticakis, CR Oc< ; mw 254.28, N 11.02Yo;
248, 244-7(1939) & CA 54, 8277( 1960)(Detn of N(CH3).C6H~
UV absorption spectra of Centr 2) 8)Anon, CO1 crysts(from gasoline), mp 74 °(Refs 1 & 2);
‘(Analytical Methods for Powders and Explosives ~’, wh pdr(by successive crystns from benz,
AB Bofors, Nobelkrut, Sweden(1960), 80-1 9) acetone, methanol & chloroform) 60.5°(by
US Spec MII...M=19719A(1960) [Methyl centrality Maquenne block)(Ref 4); Q: 8233cal/g or
(For Ammunition Use)] 2093.8kcal/mole and Q: 8247cal/g or
Centralite 2; Nitro Derivatives 2094.4kcal/mole( Refs 4 & 5); Q? lt)l.6cal/g or
Monorzitrocerrtralites, Cl ~Hl ~N303; mw 25.8kcal/mole and Q! 118.3cal or 30. l.kcal/mole
285.29, N 14.73%; were claimed to be obtained (Refs 4 & 5); Tavemier(Ref 7) gives Q: l18cal/g
by Moisak(Ref 3) on nitration of Centr 2 with and Q! 143cal/g. It is insol in w; easily sol in
nitric acid of 10-20% concn alc or benz and diffc sol in ether(Ref 1)
Dinitrocentralites, Cl ~H1 ~N405; mw 330.29, Centr 3 was prepd by Dains et al(Refs
N 16.96% One isomer, 4, 4’-Dirtitrocerztru2ite, 1 & 2) by two methods: a)Heating of equi-
oc [N(CH3).CGH4(N02)I ~; ctysts, mp 156-7° mole~lar quantities of N-ethyl.N,N’-diphenyl-
(by Maquenne block) is known(Refs 1, 2 & 4). thiourea and methylphenylcarbamyl chloride at
It can be prepd by nitrating Centr 2 with 30-70% 150-160° or b)Heating a mixt of ethylaniline,
nitric acid(Ref 3) methylphenylcarbamyl chloride and pyridine at
Trinitrocentralites, Cl ~H1 ~N~07; mw 375.29, 140°
N 18.66%. One isomer, x,x, x- Tn”nitrocentraf ite, Gelatinizing power of Centr 3 is discussed
was claimed to be prepd by nitrating Centr 2 in Ref 6
with coned nitiic acid(Ref 3) Uses: Can be used for the same purposes as
Tetranitrocentralites, Ct ~Ht ~N60g; mw 420.29, Centr 1, but is inferior to it
N 20.00%. One isomer, 2, z; 2’, .4’. Tetra~~itro- ‘ (See also Centrality 3, Analytical Procedures)
centrality, OC [N(CH3).C~H3(N02)2 ] z; small Re/s: l)Beil 12, (253) 2) F. B. Dains et al,
yel trysts, mp 192° is known. It was prepd by JACS 38, 134(1916) 3)Kast-Metz(1944), 166
nitrating Centr 2 with mixed nitric-sulfuric acid (Some props) 4)L.M4dard & M. Thomas, Mp 34,
(Refs 1, 2 & 4). Its expl props were not detd 424 & 440( 1952) (Some thermochemical data)
Hexanitrocentralite, Cl~H10N80, ~; mw 51 O.29, 5) L. M<dard, MAF 28, 480(1954 )(Same info as
N 21.96%. One isomer of unknown structure is in Ref 4) 6) G. Desseigne & J. Trenchant, CR
known; yel trysts, mp > 300°(with sublimation); 239, 769-71(1954) & CA 49, 11285( i955)(Gela-
was obtained on adding slowly a soln of Centr tinizing power of Centr 3 in comparison with
2 in coned sulfuric acid to a mixt of coned other gelatinizes) 7)P .Tavemier MP 38, 306
nitric acid with oleum, preheated to 50-600 & 328(1957) & CA 51, 15952( 1957) (Sc8ne
(Ref 2,pp 185-6). Its expl props were not detd thermochemical data)
Re/s: l)Beil 12, [236] 2)A.Apard, MP 22, Centralite 3, Analytical Procedures. Accdg to
183-7( 1926) 3)1. E. Moisak, TransKirovInstit- Kast-Metz( 1944), 167, color reactions of Centr
Kazan’(Russia), No 3, 1.59-64( 1935)& CA 29, 3 are identical with those described under Centr
4177(1935) 4) Thorpe 4(1940), 521 1. Some gravimetric and volumetric procedures
Centralite 2; Transformation Products Formed described in Kast-Metz(1944), 292-3 are
During Aging of Propellants Containing It. applicable to detn of Centr 3 in smokeless
Accdg to A. G. Garc(a”Guti~rrez, Ion(Madrid) proplnts. No other info is at our disposal
9, 165-7(1949) & CA 43, 6825(1949), Centr 2 Centralite 3, Nitro Derivatives. No info at our
forms in aged proplnts, transformation products disposal
analogous to those formed from Centr 1, Centrality 3 Transformation Products Formed
except that nitration of Centr 2 proceeds easier During Aging of Propellants Containing it. NO
and higher nitro derivs can be formed(see also info at our disposal
Centrality 2, Nitro Derivatives) In addition to Centralizes 1, 2 and 3,
there is also Centrslite 4, which was prepd
Centrality 3 or Ethylmethylcentralite(US); and investigated in France, and Butyl centrality,
Mollit 3(Ger trade name for product used as a first described by Davis in 1922
plasticizer); N.Ethyl-/i’ -metbylcarbanilide or
 C 140

Centralite 4. The name proposed by Tavemier of n-butylaniline, would be one of the methods
for Etbyltolylcentraiite or N-Ethyl-N’-tolyI.N,N’ of prepn. Schroeder et al(Refs 5) who detd its
-diphenylure% N(c7H7).CGH5 UV & visible absorption spectra, did not prep
Oc ; mw 330.43 the material but obtained it from one of the labs
$ (C, H5).C6H, working under NDRC contracts. The purity of
N 8.48% the sample is unknown, because its mp was
Tavernier(Refs 2 & 3) gives the following not detd
props: mp ca 30°, Q? l12cal/g, Q~ 138ca1/g, Uses: It can be used in proplnts for the same
specific mass 1.143 g/cm3 at 3000K and purposes as other Centralites(Ref 2 & 3), but
specific volume 0.875 cri~3/g, but does not we couId not find in the literature any form-
describe its method of prepn. Dr Walter(Ref 4) ulations using it
suggests to treat N-tolyl-aniline(in pyridine Re/s: l)Beil 12-not found 2) T. L. Davis, IEC
+ ether) with pho sgene, followed by heating the 14, 1140(1922) 3)Davis( 1943), 319 4)P~rez
resulting chloride with N-ethyl-aniline. The Ara(1945), 423 5) W. A. Schroeder et al, AnalChem
following reactions take place: 23, 1741 & 1743(1951)
N(C7H7).C6H5 Centralite, Butyl, Analytical Procedures. No
X7H7
COC12 + HN -oC( +HCl - info at our disposal
“C6 H~ cl Centralite, Butyl; Nitro Derivatives of. No info
at our disposal
HN(C2F15)
— -... C.HS> Oc<N(c7H7).C6H5 Centralite, Butyl; Transformation Products
h.
+ HCI
Farmed During Aging of Propellants Containing
R(C2H5).C6HS
it. No info at our disposal
Uses: No info at our disposal
R e~s: l) Beil-not found 2)P .Tavernier, MP Centralite RII. A permissible expl cont~ AN
38, 307 & 329(1956) & CA 51, 15952(1957) 42, K perchlorate 20, TNT 14, Na oxalare 6 &
3)P.Tavemier, MP 39, 270 & 294(1957) & CA NaCl 18%(Ref 1). Accdg to Thorpe(Ref 2) it was
53, 1715(1959) 4)H.Walter, PicArsn; private a Belgia’n expl contg AN 62, TNT 14, Na oxalate
communication(1962) 6 & NaCl 18%
Centralite 4, Analytical Procedures. No info at Re/s: l) Pepin Lehalleur(1935), 421 2) Thorpe
our disposal 4(1940), 556
Centralite 4, Nitro Derivatives. No info at our
disposal Centrifugal. See Centrifuge and Its Applications
Centralite 4; Transformation Products Formed
During Aging of Propellants Containing it. No Centrifugal Casting of Metals and Explosives.
info at our disposal Centrifugal casting of metallic objects(such as
cylindrical bodies, railway car wheels, pipes,
Centralite, Butyl; N, N’.Dibutylcarbanilide or piston rings, gear blanks, etc) consists of
N, N’.Dibutyl-N, N’-dipbenylurea, pouring the molten meral into a mold which is
OC [N(C4H9).CeH~l ~; mw 324.45, N 8.64%; rotating rapidly about its axis. It may be
wh pdr, mp ?. This compd was prepd and considered as a modified type of pressure
investigated in Germany and found to be casting which consists of making a casting
suitable as a stabilizer and gelatinize for with the aid of pressure upon the molten or
smokeless proplnts(Ref 4). Accdg to Davis highly plastic material in the die or mold(Refs
(Refs 2 & 3), it is a better gelatinize than 23467
?*)7 & 8 and numerous entries in CA’s)
either the ethyl or methyl compd, because the Railway car wheels were probably the
heavier the alkyl group, the greater the first foundry products in the US to be cen-
gelatinizing power appears to be, Beil(Ref 1), trifugally cast. The idea to do it was conceived
Davis(Refs 2 & 3), p~rez Ara(Ref 4) and in 1898 by j .C.Davis and the production began
Schroeder(Ref 5) do not describe its method of in 1902 at the East St Louis Works of American
prepn, but it was undoubtedly prepd in the same Steel Foundaries. During WWI experiments were
manner as other Centralizes, except that ethyl conducted at the Buckeye Steel Casting Co on
and methyl groups of materials used for their centrifugal castings of tubes and jackets for
prepn were replaced by n-butyl. For example, 75mm field guns, but the results were rather
interaction of I mole of phosgene with 2 moles unsuccessful. Later on, extensive research
 C 141

on manuf of gun tubes was carried out at gave slightlY lower results
Watertown Arsenal under the direction of Dr Re/s: l) Deutsche Sprengstoff A-G, GerP
F. C. Langenberg, resulting in the development 279526(1913) & CA 9, 1995( 1915)( Centrifugal
of a successful procedure(Ref 8) casting of fusible expls) 2)M. vonSchwarz &
In the Watertown ArsenaI method, the A. V~ch, Metallwirtschaft 8, 891-9(1929) & CA
metal is melted in batch lots of the required 24, 43(1930)(A review of centrifugal casting of
weight in high-frequency induction furnaces and metals) 2a)Hayes(1938), 192-3( Centrifugal
poured into a horizontally mounted mold rotating casting of cannons) 3)C. R. Hayward, c‘An
at 1300rpm while it is cooled on the outside Outline of Metallurgical Practice”, Van
with water. The mold is made of heavy cast Nostrand, NY(1952), 619( Centrifugal method
iron and machined inside to the desired shape for casting gun barrels developed at Watertown
of the exterior of the gun to be produced. The Arsenal, Mass) 4) J. G. Henderson & J .M.Bates,
finished casring has a hollow core and can be c‘Metallurgical Dictionary”, Reinhold, NY
easily bored out to the desired internal diam of (1953), 65 & 250( Centrifugal casting of metals)
the gun(Ref 3)( See also Ref 2a) 5)G. D. Clift, PATR 2381 (1956)( Centrifugal
Application of centrifugal techniques to casting of expls for 57mm HEAT shell) 6)A.D.
casting of HE charges was patented in 1913 by Merriman, “Dictionary of Metallurgy”,
the Deutsche Sprengstoff AG(Ref 1). Although Macdonald & Evans, London( 1958), 33( Centri-
it was c1 aimed that chges of high density and fugal method of casting) 7)Glossary of Ord
free of cavitation were produced by this method, (1959), 63( CentrifigaI casting) 8) C.W.Briggs,
no later work appears to have been done on this “Steel Casting Handbook”, Steel Founders’
subject, until rhe invesrigations conducted by Society of America, Cleveland, 0hio(1960),
Clift at Picatinny ArsenalfRef 5) on loading 610-ll(History of development in US of
with Comp B the 57mm T188EI0 HEAT shells. centrifugal casting process)
This type of sheIl was selected because it
could not be loaded satisfactorily by con- Centrifugal Force of Projectile and its
ventional single-pour loading procedures Utilization for Arming Fuzes and Boosters of
and it was necessary to use a special two-pour Artillery Projectiles. When a chge of proplnt in
method, In this rather slow method, Comp B was an artillery round of ammo is fired in a weapon,
poured into the shell at 85° in two increments, the pressure of resulting proplnt gases, causes
the 1st at a depth of 1~” from the base of the the projectile to move towards the muzzle. As
shell and the 2nd(after puddling the 1st pour the pressure of gases increases the speed of
and assembling a riser), to within ~’ of the proj en creases and this acceleration causes a
top of the riser setback, Rifling in the bore of the weapon
Centrifugal loading of Comp B was causes the proj to rotate as it travels towards
conducted in a specially designed and con- the muzzle. At the instant the proj leaves the
structed machine. Details of machine, capable muzzle, it has obtained its max velocity and
of accommodating two 57mm shells, is shown highest rate of spin. Setback ceases and un-
in Figs 8,9,10,’11,12 & 13 of Ref 5, While two attached components develop a tendency to
shells(with risers inside and preheated to 80°) creep forwatd. To overcome this “creep force”
were .in vertical position, Cbmp B(preheated to suitable springs are frequently incorporated
92°) was poured into them thru plastic shrouds in a fuze design. Centrifugal force is normally
and funneIs to the required level. Then the utilized to withdrew a restraining pin or
arm of the machine was rotated at 200 or 250rpm, barrier from a component to permit its expl chge
and the cradles holding the shell assemblies to align with the firing pin or another expl chge
were swung by centrifugal force outward to a in the train. Until this has occured the fuze is
horizontal position where they remained while considered ~~safe$’ for handling or shipping. A
rotation continued untiI the charges solidified. fuze is considered ‘ ‘armed” (ready to detonate)
The time required for cooling and for total when all safety devices to prevent arming have
operation was not indicated in Ref 5 been removed and the continuity of expl train
Shells loaded centrifugally at 200rpm has been established
gave slightly higher penetration on firing against Fuzes and boosters activated by
mild steel targets, than those Ioaded by two centrifugal force are design ed to operate in the
-pour process, while shells loaded at 250rpm rotational velocity range of the missile-weapon
 C 142

combination in which they are used. Rotational than by gravity. In some cases the operations
speed is dependent upon the twist of the that are not possible by gravity method(as,
rifling and the muzzle velocity, For example, for example, sepn of gummy or gelatinous
the rotation al velocity of a 37mm shell fired in solids from liquids) can be carried out by
the MIA2 gun is ca 6600@m and of a lt)5mm centrifuging
shell fired in a howitzer ca 13000 rpm(Ref 4,p For the sepn of solids from liquids,
245). This means that fuzes for projs fired there are two types of centrifuges: a) Solid
from these weapons would have different wall(such as imperforate basket type) centrifuge,
arming characteristics based on the rate of in which sepn or concn is by subsidence or
rotation flotation and b) Perforated wall(such as
Fuzes utilizing centrifugal force must be perforated basket type) centrifuge in which the
fashioned so that they will not become solid phase is supported on a permeable surface
“unarmed” as the rotational velocity decreases. thru which the fluid passes. A 3rd type is a
Some types , also are provided with devices combination of a) & b) above. Here the primary
concn is achieved by subsidence, followed by
(such as safety wire or cotter pin) to prevent
drainage of the liquid phase from the solid phase.
accidental arming during handling or shipping
preparations. Such “safer y” devices must These centrifuges can be either of batch or
be removed before firing continuous operations. For sepn of liquids,
In addn to centrifugal force, arming of there are bottle and tubular centrifuges(Ref 2,
fuzes can also be accomplished by impact, 8,10,12,14,16,19,20,21,23,25,26 & 27)
setback-, setforward- or creep forces and by A centrifuge of extremely high speed,
which wasdevelopedin 1923 by Svedberg, is
pressure of gases(Refs 1,2,3,4 & 6)
known as ultracentr~/uge, This instrument
For testing fuzes contg centrifugal
became very usefuI in the estimation of
elements, the following “arming test$~ can be
particle sizes and in the detn of mol wts of
used: The fuze is spun in an apparatus aHowed
large molecules, such as of cellulose and
to achieve different speeds of rotation and the
NC(Refs 3,4,6,7,9,11,17,18,20,22 & 24)
lowest speed at which the centrifugal elements
SpeciaI laboratory centrifuges used in
move outward is recorded, This insures arming
analysis and research are described in Refs
of fuzes at minimum speeds expected in the
15,17,20,22, & 24
weapon. Setback elements of fuzes can be
Centrifuging has been used extensively
tested by dropping them in a “drop-test
in chemical industries, including the manuf
machine” from a height of drop to simuIate
of expls. For example in the DuPont method
the minimum setback in the weapon(Ref 3,p 135)
of manuf of NC(See this VOI of Encyclopedia,
(This section was prepd in coHaboration with
under Cellulose, Nitro; Manufacture), the sepn
A. B. Schilling of Pi cArsn)
of NC from the spent nitrating acid is done by
Refs: l)Hayes( 1938), 580-1 2)Anon,
centrifuging. Another example is the sepn of
‘tAmmunition Inspection Guide”, TM 9-1904
TNT ctpts from ‘ %ellite” soln(Na2S03 in
(1944), 322 3)0hart(1946), 127-30& 135 4)
water) and then from wash water, which will
Anon, “Artillery Ammunition”, TM 9-1901
be described under Toluene, Trinitro; Manu-
( 1950), 242-5 5) B. A.Gay, “A Study of the
facture. It can be done by centrifugation or by
Effects of Setback and Centrifugal Force on
vacuum ,filtration using a “Nutsch”
Non-solid Shell Fillers”, P.4TR 1785(1951)
Various centrifuges used in the manuf of
(Conf)(Not used as a source of info) 6)Anon,
NC and expls are described in Ref 1
“Ammunition General”, TM 9-1900(1956),
Walkup(Ref 13) patented in 1949 a basket
134-9
type centrifuge in which the slurry of
explosive particles is fed continuously into a
Centrifuge and its Applications. Centrifuge
rapidly rotating cylindrical container with
is an apparatus that subjects a material to a
perforated walls. The explosive, as it looses
high centrifugal field by very rapid rotation.
the slurry liquid thru the perforations, first
As the centrifuging field can be varied by
forms a lining of conoidal surface and then,
changing rotation speeds or dimensions, and
subsequently fe~ particles climb along this
as these fields are always much greater than
surface and are propelled outwardly from the
gravity, aI1 operations can be performed more
mouth of the container over the edge of the
rapicfIy and in a lesser space by centrifugation
 C 143

lining 1039-69 (Various types of ultracentrifuges) &

Refs: 1)0. Griindlich, SS 5, 352-7, 413.18, 1069-96 (Methods of measurements by ultracentri-
434-8, 458-61 & 478-8(1910) & CA 5, 1841(1911) fuges) 21)1.M.Abramovich et al, RUSP 103110
(Con st~ction & oPeration of various centrifuges (1956) & CA 50, 16204( 1956)(A continuously
used in manuf of NC & expls) 2)Ullmann 10 operating centrifuge provided with an automatic
(1932), 577-87(Zentrifugen) 3)T.Svedberg, discharge of udersized material from the bottom)
IEC, AnalEd 10, 113-28( 1938) (Ultracentrifuge 22)E.Wiedemann, Dechema Monograph 26, 330-60
and its field of research) 4) T. Svedberg & K.O. (1956) & CA 51, 3196( 1957)(Development &
Pedersen, “The Ultracentrifuge”, Clarendon application of a new ulttacentrifuge and some
Press, Oxford( 1940) 4a) D. R. Cameron, PATR new types of lab centrifuges) 23)1. E. Broadwell,
1062( 1940)( Removal of surface moisture from Chem & ProcessEngrg 38, 432-6(1957) & 40,
proplnts by centrifuge) 5)H.Banning, USP 86-90( 1959)(Centrifuging; a review) 24)E0
2353983(1944) & CA 38, 6095( 1944)(Description Wiedemann, Helv 40, 1831-4(1957) & CA 52,
of centrifugal separator for purification of 2466( 1958)( Lab centrifuges & ultracentrifuges)
cellulose) 6)N.Gral~, ‘Sedimentation and 25)J.E.Flood Jr., IEC 50, 428-9(1958) & 51,
Diffusion Measurements on Cellulose and 344-5( 1959) (Centrifugation; reviews under
Cellulose Derivatives”, Dissertation, Uppsala, ~~Unit operations”) 26) W. Budeberg, Chem-
Sweden(1944) 7)1. JuIander, ‘ ‘Studies of Nitro- Tech(Berlin) 10, 341-5(1958) & CA 54, 16043
cellulose”, Dissertation, Uppsala(1945) 8)].0. (1960)(A review of various industrial centrifgues)
Maloney, IEC 38, 24-5(1946) and succeeding 27)J.W.LOy, USP 2921969(1960) & CA 54,
years up to 1956, (Centrifugation, under 7257( 1960)( Centrifugal crystal purilier)
Unit Operations) 9)T.Svedberg, JPhysCollChem
51, 1- 18(1947)(Physico-them studies of cellulose Centrifuge Test for Exudation. It is one
molecule by ultracentrifugal sedimentation) the tests used to determine the amt of liquid
10)P.G.Romankov, KhimProm 1947, NO L 16-19 ingredients(such as NG, NGu, etc) of dynamites
& CA 50, 15139(1956)(A review of info on the and to separate them from solid ingredients
newer design of filters & centrifuges for (such as AN, sawdust, etc), This test can also
continuous sepn of hard to filter sediments) be used to det exudation in commercial TNT’s.
11)1. Julander, JPolymerSci 2, 329-45( 1947) Here “exudate” consists usually of an
(Ultracentrifugal investigations of cellulose eutectic mixt of DNT with isomers of TNT,
& its derivs) 12)Kirk & Othmer 3(1949),501-21 mainly beta and gamma
(Centrifuges and centrifugal sepn) 13)L.E. Centrifuge test is considered to give
Walkup, USP 2490108(1949) & CA 44, 1709-10 truer values for exudation than other tests
(1950)( Basket-~pe centrifuge for expIs [See Ref 3,P XI, under Exudation(or Sweating)
industry) 14)Perry( 1950), 992-1013(Centrifuges) Tests 1 particularly the Pressure Test(See
15)S.Oka & G.Mute, JapanAnalysr 1, 136-40 Ref l,p 421), This is because in the Pressure
(1952) & CA 47, 4781( 1953)(Rapid analysis by Test, the sample of dynamite is subjected to
centrifugal method) 16)RiegeI, ChemMach pressure of 80psi and as this pressure is much
(1953), 367-89(Centrifugals) 17) J. ReiIly & greater than any that will occur in practice, it
W. N.Rae, { ‘Physico-chemical Methods”, Van may be considered unrealistic. In employing
Nostrand, NY, VOI 2(1954), 215-19( Centrifugal the centrifuge test, the pressure upon any parr
action) & 220-25 (Ultracentrifuge) 18)J. W. of the expl is very moderate but is sufficient
Williams, JPoIymer Sci 12, 351-78( 1954) (Sedi- to remove any liquid film of too great a thickness
mentation analysis by ultracentrifuge) 19)J. E. that covers the particles of absorbent and which
Flood, ChemEngrg 62, N06, 217-27(1955) might cause the exudation
(Centrifugal for sepn of solids from liquids) The procedure for centrifugal testing of
20)A. Weissberger, Edit, “Physical Methods of dynamites, as was used in England, is described
Organic Chemistry”, Interscience, NY;VO1 L in Ref l,pp 421-2
Part 1(1956), 542-8, 563-606, 655 & 718-23 This test was also adopted and modified
(Centrifuges and centrifuge filtration & by the USBurMines and is described in Ref 2, pp
ultrafiltration); Ibid, VO1 I, P t 1(1959), 224-7 25-6). The apparatus consists of two tared
(Centrifugal sedimentation), 226-7(U1tracentri- perforated porcelain Gooch crucibles, each
fuges) & 348-9( Centrifugal filtration); Ibid, attached above a solid crucible and each
VO1 1, Pt 2(1960), 101 l-39( Centrifugal ~alYsis)* ensemble secured by means of a holder CO each
 C 144

end of the arm of the lab centrifuge. After & Ca carbonate O-1.5pts(Ref 2)
placing in each Gooch crucible an 8g sample, Re/s: l)J.B.Bronstein & C.E.Wailer, USP
the radius of rotation of bottom of each 1188244(1916) & CA 10, 2150(1916) 2)Ibid
outermost crucible is adjusted to 7cm and the USP 1188245(1916) & CA 10, 2150(1916)
temp in the room to 20°. The centrifuge is
rotated by hand for 5mins at the rate of 600rpm. Cerenkov Radiation. See Cherenkov Radiation
The Gooch crucibles are then removed, wiped
on the outside and weighed. If the loss in wt Ceresine or Mineral Wax. See under WAXES
of sample is greater than 5%, the expl has
failed to pass the test Ceric-Ammonium Nitrate ar Cerium-Ammonium
Gelatinous expls(such as blasting Nitrate. See under Nitrates
gelatin and gelatin dynamites), or plastic expls
(such as PETN or RDX with ca IO% of oil) do Ceric-Ammonium Sulfate or Cerium-Ammonium
not respond to centrifuge test although they Sulfate. See under Sulfates
sometimes exude in storage. For testing
exudation of these expls, the so-caHed ‘tBritish Ceric Oxide or Cerium Dioxide. See under
Test”, described in Ref 2,pp 26-7, can be used Oxides
R e/s: l)Marshall 2(1917), 421-2 2) C. E. Munroe
& J. E. Tiffany,’ ‘Physical Testing of Explosives”, Ceric Sulfate or Cerium Sulfate. See under
USBurMines Bull 346( 1931), 25-6 3)PATR Sulfates
2700, Vol l(1960),p XI
Cerium, Ce at wt 140,13,at No 58; one of the
Cereal Dust Explosions. See Dust Explosions “rare earth” elements; gray, ductile, maleable
metal which tarnishes in moist air; d 6.78; mp
Cereal Meal. The coarsely ground and unbolted 645°, bp 1400° ; sol in dil acids; insol in cold
grain of cereals, such as rye, corn, wheat, w & slowly oxidizes in hot w; forms numerous
barley, oats, etc(Ref 2). Some cereal meals alloys & salts. It occurs in monazite sand
have been used as fuel and sensitizer components which is ?n orrhophosphate of thorium and rare
of industrial expls. Eg: a) French AN dynamite earths. Cc-Fe pyrophoric alloys are used as
-AN 45, NG 40, Na nitrate 5 & cereal meal 10% sparking flints for lighters, tracer bullets & for
(Ref l,P 341) b)Ger AN expl-~ 61.0, Na military signaling. Ce metal is used as com-
nitrate 3.o, cereal meal 7.5, glycerin 3.0~ MNT ponent of some rocket proplnts and in alloys
1.0, NG 4.0 & K or Na chloride 20.5%(Ref I,p for jet engines. Toxicity , fire & expln hazards
352) c)Ger Carbonit 11-NG 25.0, K nitrate 34.0, of Ce are discussed in Ref 5. Ce alloy, called
Ba nitrate 1.0, cereal meal 38,5, spent tan Miscb Metal: Ce 52, Nd 18, Pr 5, Sm 1 & other
bark meal 1.0 & Na carbonate 0.5%(Ref l,P 353) substances(such as La, Ca, Al, C, Si & Fe)
d)Ger Carbonit IV-NG 30.0, Na nitrate 24.5, 24%, has many applications. Mixt of Ce &
cereal meal 40.5 & K bichromate 5. O%(Ref l,p Th oxides is used in Welsbach incandescent
353) gas mantles
Re/.s: l)Davis(1943), 336,341,352 & 353 2) Lindeman & Hafstadt(Ref 2) patented
Kirk & Othmer 3(1949), 634-47 detonating expls contg finely pulverized alloy
of Ce with Mg or Al with oxidizing agents,
Cereal Screenings. Refuse after screening of such as K chlorate, AN, K permanganate or K
cereals, which may include bran, small bichromate
imperfect grains, weed seeds> etc, was R e/s: l)Mellor 5(1924), 586-676 (Cerium family
proposed for use as a component of some of rare earths) 2) T. Lindeman & M. Hafstadt,
detonating expls, such as those based on NS NorwP 44012(1927) & CA 22, 4251( 1928) 3)
(Nitrostarch). Eg: a)NS 30-45, TNT 2-10, AN Thorpe 2(1938), 507-8 4)Kirk & Othmer 3(1949),
10-30, Ba nitrate(which in part may be 634-47 5)Sax(1957), 448-9 6) CondChemDict
substituted by Na nitrate) 45 & sulfur 0-10 (1961), 241 & 755-6( Misch Metal)
parts are mixed with “‘cereal screenings” 2-3
& Ca carbonate O-O.5pts(Ref 1) b)NS 26-3o, Cerium Azide. See Cerium Triazide under
r ‘cereal screenings 5-8 & sulfur 0-5pts xe Azides, Vol l,p A528-R of this Encyclopedia
mixed with Na nitrate 58-65, paraffin oil 0.4-0.5
 C 145

Cerium Compounds for Smoke Production. A of Cs & Rb are as effective flash reducers for
number of Ce compds contg mixts were proposed colloidal proplns as salts of K. Cs metal and
by J .DeMent, USP 2995526( 1961),P 8, as its alloys are used in manuf of vacuum tubes
smoke-producing pyrotechnic compns and photoelectric cells(Ref 3)
Re/s: l)Mellor 2(1922), 449,451 & 468 2) Gmelin,
Cerium Dioxide. See Ceric C)xide under Oxides Syst Nr 25( 1938) 3)Kirk & Othmer 1(1947),
453-5 & 3(1949), 648-51 4)H.Muraour & G.Aunis,
Cerium Hydroxydiazide. See Vol l,p 528-R of MP 35, 296~1953) & CA 49, 13651(1955) 5)Sax
Encyclopedia (1957), 450-2 6) CondChem Dict(1961), 243

Cerium Nitrate or Cerous Nitrate. See under Cesium Acetylide-Acetylene. See Vol I,p
Nitrates A72-L of Encyclopedia

Cerium Nitride. See under Nitrides Cesium Azide. See VOI I,p A528-R

Cerium Sulfate. See under Sulfates Cesium Nitrate. See under Nitrates

Cerous-Ammonium Nitrate. See under Nitrates Cesium Nitrites. See under Nitrites

Cerous Nitrate. See under Nitrates Cesium Perchlorate. See under Perchlorates

Cermets(Ceramels). Ceramic-metal mixts prepd Cesium Periodate. See under Periodates

by powder metallurgy techniques in which a
powdered mixt of refractory material(such as Cesium Permanganate. See under Permanganates
metal silicates, oxides or carbides) is molded
to the desired form with a metal or an afIoy Cetane Number or Cetane Rating. It is a
(such as of Co, Ni, Fe, Al, Cr or Mo) md a measute.of ignition value of a Diesel fuel oil
brazing agent(such as Nb, Ta, Ti or Zr) and (comparable to the octane number rating for
then subjected to high temp and pressure. The gasoline), expressed as percentage by volume
resulting items combine favorable props of of n-cetane [ l-hexadecane, CH3.(CH2) IA .CH3;
components(such as strength and resistance CO1 liq, bp 287.5°, obtained from petroleum] ,
to high temp, oxidation & thermal shock) and which must be mixed with l.methylnaphthalene
are suitable for use in gas turbines, in order to obtain the same ignition lag as the
nuclea~ reactor mechanisms and rocket & oil being tested
turbojet engines(Refs 1,3 & 5). Use of cermets Ref.s: l)CondChemDict( 1961), 245 2)Merriam
in ordnance is discussed in Ref 2 -Webster’s( 1961), 368
17e/.s: l) G. C. Deutsch et al, “A Review of the
Development of Cermets”, Advisory Group for CG 14. A pre- WWII Ital smokeless proplnt: NC
Aeronautical Research and Development, NATO, 60, NG 25, DNT(solid) 10 & Centr 5%
Paris, Report 185(1958) 2)] .M.Woulbroun, Ordn Re/: M.Gha & G. Guastal~a, Chim & lnd(Paris)
44, 501-5( 1959)( Cermets for Oraance) 3)JcR= 29, 272(1933)
Tinklepaugh & W. J3.Cr~dali, “Ce~ets”,
Reinhold, NY(1960) 4)CondChemDict( 1961), CH-6, RDX Composition(U). See L. D. Hampton,
241-2 NavOrdRept 6880( 1960)( Conf)

Cesium or Caesium, Cs, at wt 132.91, silver Chaff, Rope, and Window Countermeasures.
-white, soft ductile metal, d 1.90, mp 2$3°, bp Cba// is an electromagnetic wave reflector,
6W0; sol in acids & ale; decomp by w; can be consisting of a thin narrow piece of metal,
prepd by thermochemical reductiofi of CSCI with designed to be released into the atmosphere
Ca. Toxicity and fire & expln hazards of Cs are (either by dropping from a plane or shot into
discussed by Sax(Ref 5). Liquid Cs has been the air in projectiles) to act as a counter-
suggested for ion propulsion systems and measure against enemy radar. A grouping of
plasma for thermoelectric conversion(Ref 6). several pieces is called cbafl set. A similar
Muraour & Aunis(Ref 4) have shown that salts device, but longer, is called rope. A small
 C 146

parachute may be attached to each piece to Oxford( 1935) 2) C. Dainton c‘Chain Reactions
reduce the rate of fall. Another similar device, -An Introduction”, Methuen, London( 1956)
but sometimes metallized only on one side, is 3) Condchem Dict( 1961), 246 4)Merriam-Webster’s
called window. Original use of the word ( 1961), 370
‘*window” appears to have been strictly a
matter of code Chakatsuyaku. Japan for TNT
Re/: Glossary of 0rd(1959), 63,248 & 319 Re/: OpNav 30=3M( 1945), 26

Chaff Shell or Window Projectile. Special Chakoor Powder(1903): K chlorate 70, sugar
projectile contg “chaff”, “window” or “rope” 28 & wax 2%
which is injected in the air to confuse enemy R e/: Giua, Trattato, 6(1959), 398
radar
Re/: Glossav of 0rd(1959), 319 Chalcone and Derivatives
Cbalcorze(Benzalacetophenone or Betaphenyl-
Chain(in Demolition). A number of units of acrylophenone), (Chalkon in Ger),
demolition charges cast on a length of
detonating cord with a short section of cord C6Hg. e H:~H. CO.C H ; mw 208. 25; yel trysts,
between adjacent units mp 57-8°, bp 345-8 8(with ‘. S1 decompn). Other
Re/: Glossary of ord( 1959), 63 props & prepn in Ref
Ref.’ Beil 7, 478,(260) & 423
Chain Rammer. A power-driven chain-linkage MorzorzitrocbaZcorzes, Cl ~H1 , N03; rnw 253.25,
device for loading a projectile into the breech N 5.53%. Seven isomers: 2-, 3-, 4-, 2’-, 3’-,
of a large caliber cannon, such as in turrets. 4’- and a-Nitrochalcones are listed in Ref
The power rammer assembly is attached to the Re/: Beil 7, 482-3, (263) & [482-3]
racer immediately in rear of the cannon. This Dinitrocbulcorzes, Cl ~Hl 0N205; mw 298.25,
system is used to increase the rapidity of fire, N 9.39%. Five isomers: 2,3’-, 3,2’-, 3,3’-,
and to insure uniform seating of hea~ projs 4,3’-, 4,@-Dinitrochalcones are described in
Re/s: l)Hayes( 1938), 309=11 2) Glossary of Ref
Ord(1959), 63-4 Re(: Beil 7, 483 & [429]
Trinitrochalcones, Cl ~HQN~07; mw 343.25,
Chain Reaction. It is a reaction that once N 12.24%. Following isomers are described
started maintains itself by interaction of in the literature: 3,3’, S’- Trinitrochalcone or
starting materials with transistor reactive 3,5. Dinit?u@-(3”nitrobenzal) -aceto#.renone,
products, such as molecules, atoms or nuclei ~ 02N.C6H4.CH:CH. C0.CeH (N02)2; yel
and more of the reactive products being formed crysts(from AcOH), mp 226 8; sol in AcOH,
as they are consumed. M. Bodenstein of Germany acet & ethyl acetate; insol in alc or ether. Was
was the first to point out(in 1913), that reaCtiOns prepd by treating 3,5-dinitroacetophenone with
might proceed by a chain of subsidiary reactions. 3-nitrobenzaldehyde in alcoholic HCl(Refs 1 & 3)
Since then the subject has developed rapidly 3,3”, a- TrinitrocbaIcone or 3, @Dinitro-e{3
and is now a well established branch of -nitro. benzylidene)-ac etophenone, 02N. CG H4.-
reaction kinetics CH:C(N02).C0.C6 H4.N02; lt yel crysts(from
Since WWII, the term “chain reaction” ethyl acetate)> mp 152.5-1 54°; very sol in
frequently refers to self-propaf@ting fission of boiling AcOH; sol in acet, benz & chlfi diffc
atomic nuclei continued by the further action col in CC14; in sol in ligroin or water. Was
of one of the fission products. For ex~ple) prepd by treating 3, 3’-dinitrochalcone with
when a U-235 nucleus absorbs a neu~ns it absol nitric acid at 0°, either alone or in
splits ot fissions releasing a great amt of presence of AcOH or Ac20(Refs 2 & 4)
energy and emitting many neutrons, which 4,3’, a. Trinitruchalcone or 3, @-Dinitro.@
may, in turn, be absorbed in other U-235 -(4.nitrobenzyl idene)- acetophenone,
nuclei to propagate the reaction 02 N. C6H4.CH:C(N02).C0. C6H4.N02; yel
(See also Atomic(or Nuclear) Energy, VOI 1 ndls(from et acet), mp 135°; SO1 in the s~e
of this Encyclopedia,p A500-A504) solvents as 3,3’ ,a-isomer. Was prepd by
Re/.s.’ l)N.N.Semenov, “chemical Kinetics nitrating 4, 3’-dinitrochalcone with absol nitric
and Chain Reactions” ~ Claendon press> acid(Refs 2 & 4)
 C 147

Re/s: l)Beil 7, 483 2)Beil 7, [430] 3)L. and in a revolver, it is a hole in the cylinder
Berend & F.Heymann, JPraktChem 69, 470 for inserting a cartridge(Refs 1,2,3,5 & 6)
(1904) 4)J. van der Lee, Rec 47, 426-9& In arecoillessrifle, the chamber is
430(1928); CA 23, 116(1929) considerably larger than the cartridge case;
T#tranitrocAu2cone, Ct ~HeN409; Perztarz@o. therefore the complete round is suspended in
chalcone, Cl ~H7Ng01 , and Hexanitrocbalcone, the center of the chamber, Ctge cases in these
Cl ~H6N60f ~-not found in Beil and in CA’s rounds are perforated in order to allow escape
1907-1960, incl of gas to the sides of the chamber and then to
atmosphere thru openings(orifices) at the rear
Chaluer de combustion. Heat of combustion of the chamber in breechblock(Ref 3,pp 167-8)
In rockets, there are two kinds of
Chaleur de detonation(ou d’explosion)(Fr). chambers: the “combustion chamber” and
Heat of detonation(or explosion) “thrust chamber’ ‘(See Ref 4)
Re/s: l)Hayes(1938), 162 & 165 2)Anon,
Chaleur de formation. Heat of formation ‘fFundaments-s of Small Arms”, TM.9-2205
(1952), 72, 83 & 95 3)Anon, “principles Of
Chaleur specifique(Fr). Specific heat Artillery Weapons”, TM 9-3305-1(1956) 26 &
167-8 4)RocketEncycl( 1959), 75-8, 96-7 &
Chalk. A native amorphous calcium carbonate 517-24 5)Glossav of Ord( 1959), 64 6)Merri~
composed of calcareous remains of minute -Webster’s(1961), 372
marine organisms. It can be used as antacid
or stabilizer in expl and proplnt compns(See Chambering is the phase of small-arms operation
Calcium Carbonate, under Carbonates) that deals with the placing of the round into the
Re/s: l)Hackh’ S( 1944), 185 2)CondChemDict chamber
(1961), 247 Re/: Glossary of Ord(1959), 64

Chalon Apparatus. A very simple app for detg Chamber Pressure. When a chge of proplnt is
brisance of expls. It consists of two lead ignited within a gun chamber, it bums giving
cylinders 40mm in diam & 30mm high, placed off gases which develop pressure, serving o
one on top of the other vertically with the drive the projectile towards the muzzle, This
lower one resting on a cast iron foundation and pressure increases gradually until it reaches
the upper one covered with a steel disc, 3mm a certain maximum, called t ~eak pressure”.
thick. A chge of expl(40-50g), contained in a After this the pressure decreases until the
zinc can, covered with a Iid(contg one central proj emerges from the gun and then it drops
hole thru which is inserted either a Bickford quickly to atmospheric. Peak pressure can be
fuse or wires of elec detonator) is placed on either calcd or detd experimentally by means of
top of the disc and is exploded. The compression devices known as “copper crusher gage” and
of upper lead cylinder, caused by expln, is “piezoelectric gage”. These devices, however,
measured and compared with that produced by do not record the time necessary to reach the
PA, which serves as a “standard” peak, nor the rate of increase and subsquent
Re/s: l)P. F. Chalon, c‘Les Explosifs Modemes’: decrease of pressure during the movement of
B~ranger, Paris(191 1), 452-3 2)Pepin Lehalleur proj. This info can be obtained by means of
(1935), 64 devices called “recording pressure gages”. In
one of them, known as “Bichel Pressure Gage”,
Chambre à poudre(Fr). Proplnt chamber of a the pressure acts on a piston which, in turn,
cannon causes compression of a spring and, at the
same time, traces a mark on a drum which is
Chamber of a Weapon In general, it is the part rotated very rapidly by means of an electric
of a weapon in which the firing charge is motor. In another device, called ‘ ‘Petavei
placed. In a cannon, the chamber(also called Recording Manometer”, the motion of piston
‘ ~owder chamber”), is the part of gun barrel (usually very small) is magnified many times
betw the obturator or breechblock and the by causing it to deflect a small mirror which
forcing cone. In a weapon with fixed ammunition, throws a beam of light onto a sheet of
it is the space occupied by the cartridge case; photographic paper wound on a drum which is
 C 148

rotated rapidly(Refs 1 & 4) picrates with oxidizers, such as chlorates

Ohart(Ref 3,pp 4 & 5) lists the following and / or nitrates. Eg: a) Blasting expl: MNN
maximum chamber pressures, in psi for some picrate 28, AN 45 & K chlorate 27% b)Military
of the US weapons used during WWII: 75mm expl: DNB picrate 57, AN 17 & K chlorate 26%
gun 3600, 75mm howitzer 29000, 60mm smooth c)Militaty expl: MNN pi crate 33 & K chlorate
-bore trench mortar 6000, 8 lmm smooth-bore 67%
trench mortar 6000 and 4.2-in rifled-bore Re/: Colver(1919), 695-6
chemical mortar 9000. Ohart also gives(Ref 3,p
88, Fig 39) typical pressure and velocity Channel Black. A variety of carbon black(qv)
curves for artillery projs obtained at the made by’ impingement of a luminous natural-gas
Ballistics Research Laboratory, Aberdeen flame against and iron plate from which it is
Proving Ground, Maryland scraped at frequent intervals
In rockets, the chamber pressure is the Re/: CondChemDict(1961), 248
pressure developed as a result of burning of
solid or liquid proplnts in the combustion Channel(or Canal) Inclusion Compounds. See
chamber. It is usually measured thru the under Clathrates and Other Inclusion Compounds
injector face or near the injector end of the
thrust chamber by providing a small passage Cha6yaku. A Japan expl contg PA 75 & TNT
for the gas to press against some external 25%, used during WWII as a bursting chge for
measuring device(Ref 5) aerial bombs
R efs: I)Marshall 2(1917), 444-53 2) Hayes Re/s: l)OpNav 30-3M( 1945),26 2) Antonelli
(1938), 57,65,72,77 & 92-6 2a)Anon, “Ammuni- (1960), 29-30
tion Inspection Guide”, TM 9-1904(1944), 322
3)Ohart(1946), 4, 5 & 88 4)Glossary of Ord Chapman Explosive, patented in England 1888,
(1959), 219-20 5) Rocket Encycl(1959), 77-8 was proposed to replace MF in primers. Its
compn was: K nitrate 51.9, P(amorphous) 15.9,
Champion Powder. A blasting, low-grade NG K chlorate 10.9, Mg(powder) 6.1, Mn dioxide
expl developed in the Iate eighties by the 5.2, HgO 4.0, K carbonate 2.0, sugar 2.0 &
California Powder Works, San Lorenzo, Calif rosin(powder) 2.0%
to compete with “Judson Powder”, also called Ref.’ Daniel( 1902), 127
“RRP’ ‘(Railroad Powder), Both Champion and
Railroad powders were similar in compn and Chapman-Jouguet Theory. See under Deto-
were used mostly for bank blasting in RR nation, Theories of
construction. The exact compn of Champion
Powder is not given in the Ref, but RRP was Char de Combat (Fr). Tank
prepd by melting together(with constant
stirring) 15parts of sulfur, 3ps rosin, 2ps Characteristic Data(Safety) for Explosive
asphalt, 70ps of Chile saltpeter & 10PS of Materials. Under the title “Sicherheitstechnische
powdered anthracite coal. The hot mixt was Kenndaten explosivf2higer Stoffe”, H. Koenen,
poured on the floor and granulated by raking K. H.Ide et al, describe in Explosivst 1961,
until cold. The resulting solid grains were 4-13, 30-42 & 195-7 detns of the following
coated with 5% NG, RRP and Champion Powder characteristics: density(Dichte), heat of
produced on expln a ‘{heaving” rather than formation(Bildun gsw~rme), heat of explosion
“shattering” effect (Explosionsw~me), temperature of explosion
Re/: Van Gelder & Schlatter(1927), 338 & (Explosionstemperatur), ignition temperature
507-8 (Entziindungstemperatur), chemical stability
at 75°(Chemische Stabilit3t bei 75° ), ignitability
Chan6yaku. A Japan expl contg TNT 70 & DNN (Entuziindlichkeit), duration of burning
(dinitronaphthalene), 30% used during WWII as (Brenndauer), heating under confinement
a bursting chge for artillery shells (Erhitzen unter Einschluss), friction sensitivi-
Re/s: l)opNav 30-3M( 1945), 26 2) Antonelli ness(Reibempfindli chkeit), impact sensitiveness
(1960),29 (Schlagempfindlichkeit), expansion in lead
block(Ausbachung im Bleiblock, ) and sensitiveness
Chandelon Explosives(1888). Mixts of org to detonation-shock(Sensibilit2t gegen
 C 149

Detonationsstoss) Charbonneaux Explosives: a)Industtial expl:

Twenty expI substances were examined K chlorate 75 & saccharine 25%(Refs 1 & 2)
and values of their characteristics are given and b)An expl proposed as a bursting charge
in table,pp 196-7 in shelLv: Na nitrate 58.8, PA 23.5, MNN 11.8
& Pb dioxide 5.9%(Ref 3). Nitrated petroleum
Characteristic Product of Berthelot (Produit or nitrated turpentine may be substituted for
caracteristique de Berthelot$ in Fr). See MNN to form a proplnt for rifIes
Berthelot Characteristic Product Re/s: l)A.E.Charbonneux, USP 886038(1907)
& CA 2, 2622(1908) 2)Esca1es, Chlorat$pr
Characteristics of Explosives and Propellants (191o), 102 3) A. E. Charbonneux, USP 1174546
(Caract~ristiques des Explosifs et des (1916) &CA 10, 1435(1916)
Poudres, in Fr). In France, the following
properties are considered “caractdristiques”: Charbonnier, P(1862-1936). Fr general of
heat of formation(chaleur de formation); heat Naval artillery, specializing in ballistics.
of explosion(chaIeurde I’explosion); specific Author of several papers and books on
volume(volume sp~cifique)(vol of gas in liters ballistics, including “Trait6 de Bali stique
liberated by Ikg of the expl, calcd to 0° & Exte$rieure”, Gauthier-Villars, Paris, vol 1
760mm with w as vapor); temperature of (1921) & vol 2(1927)
explosion( tempt?rature de 1‘explosion)(absol Re/: Anon, MAF 15, p VII of 2nd fascicule and
temp reached by gases on expln); co,volume pp II-X of 3rd fascicule( 1936)( Obituary and
(See Ref 2,pp 67-70); pressure of explosion in brief biography)
cIosed vessel) (pr&ssion de l’explosion en vas
C1OS); velocity of detonation(vitesse de Charbonnier’s Contributions in Ballistics. A
d~tonation); work performed by the explosive complete list of his publications is given in
or potential of the explosive)(travail fourni par Ref 2 including his important contributions in
1‘explosif ou potentiel de l’explosif); impact “bterior Ballistics”, and in Ref 3 in “Exterior
sensitiviness)( sentibilit~ au choc de mouton); Ballistics”,
force of explosive(f)(force de l’explosif)(See R e/s: l) Anon, MAF 15, pp 1X.X111 of 3rd
Ref 2,pp 70-l); brisance by c~sher test fascicule( 1936) 2)M.E.Serebriakov, “Interior
(brisance par ~crasement de crusher); brisance Ballistics”, oboronizdat, MOSCOW(1949),
by Kast’s formula(brisance d’apres Kast); translated by Dr. V. Nekrassoff for Aberdeen
power by lead block test(CUP par essai au Proving Ground, Md,p 33 3)M.Garnier, “La
bloc de plomb)(See Ref 6,p XXV, under Balistique Ext4rieure Moderne en France”,
Trauzl Test); and constants of Muraour K, & published in MAF 28, 117-34(1954); pp 131-5
K2(constantes de la vivacit~ de Muraour K, et (Method of Charbonnier for calcn of trajectories)
Kz(relative quickness of proplnts)(See Ref 2,pp
90-2) Charcoal. A black amorphous substance; a
Tavernier detd the following characteristics form of carbon derived from the incomplete
of some French proplnts: calorimetric potential combustion of animal or vegetable matter
(potentiel calom4trique)(Refs 3 & 4), volume of (Ref 2). When a pure form of charcoal is
gases(voIume des gaz)(Ref 3) and temperamre desired, it is derived from sugar. Its method of
of explosion(temptramre d’explosion(Ref 4). prepn by calcination of sugar heated to ca
He also detd the influence of some inorganic 800° is described in Ref 3. This method is
additives on characteristics of proplnts(Ref 5) considered superior to the treatment of sugar
Re/s: l)pepin Lehalleur(1935), 48, 84& 94) with coned H..#04. Toxicity, fire & expl
2)H.Muraour, “Poudres et Explosifs”, Presses hazards of charcoaI are discussed in Ref.4
Universitaires, Paris(1947), @-92 3)P* Charcoal is used in various them
Tavernier MP 35, 233-72(1953) 4)Ibid 37, processes, as a decolonizing & filtering
225-68( 1955) 5)Ibid 38, 267-99(1956) 6)B. mediumt as absorbent~ in pharmaceutical PrePns
Fedoroff et al, PATR 2700, VOI I(1960),PP & plastics and as a component of propellants,
VII, IX, X, XV, XVI, XVII, XX,XXI, & XXVI BkPdr, pyrotechnics & of other expls(Refs 1 &
5). Charcoals used by the US Armed Forces
Carbon(Fr). Charcoal must compi y with the applicable specifications
(Ref 6)
 C 150

Marshall, Dict( 1920),PP 108-9 lists 33 demolition blocks assembled around detonating
expls in which charcoal is used as one of the cord and dropped with attached parachute to
ingredients keep the chain elongated. Another “line
Refs: l)Davis(1943), 28,39,42,48,49,52,66,72, chsrge”s known as cutting charge is in the
76,79,83-9,92-3,95,99,105,117, 2)Hackh’s shape of a trough and contains a wedge shaped
(1944), 186 3)~orgSyn* 2(1946), 74-5 4)Sax or curved liner. When detonated on a thick
(1957 ),455-6 5)CondChemDic41961), 248 sheet of metal it produces a straight cut
6)uS Specifications: J AN-C- 178A( I)(Charcoal (shearing). A similar charge also used for
for use in ammunition); LLL-C-25 l(Chsrcoal); cutting is called wedge charge. It is provided
MIL-C-17605A(charcoal, activated, technical, with a wedge-shaped cavity, lined or unlined.
unimpregnated); MIL-C- 13724A (Charcoal, A demolition expl of great length is known as
activated, impregnated, ASC); and MIL-C linear charge
- 10202A (Charcoal, activated, technical) The so-called spotting charge, consists
(See also under BLACK POWDER & under of a small amt of BkPdr in a practice(or
Carbon) occasionally in service) bomb, shell or mine
to show( by producing some smoke) the location
Charcoal, Analytical Procedures. Analysis of of its point of functioning. An expl chge
wood charcoal, covering moisture, volatile covered with an adhesive substance to make it
matter and ash is given in ASTMStds( 1961), stick against an object when thrown or planted,
Part 6, Method D1762-60T,pp 860-2 is known as sticky charge, also called “sticky
grenade”. An expl consisting of a number of
Charcoal, Brown. See Brown Charcoal and also demolition blocks(total wt ca 151bs), tied
Davis(1943), 42 together, capped, fuzed and mounted on the
end of a pole is called pole charge. An expl
CHARGE. An explosive charge is a given chge contained in a booster is called
qusnti~ of expl, contained in a bomb, shell, booster charge and in a detonator is
rocket warhead, torpedo, mine, grenade, fuze, detonator charge. In a shell provided with a
demolition or pyrotechnic item. If the chge, deep cavity(which is intended to seat a
also called filler, is used for breaking the proximity fuze, and other type of a fuze can be
casing of a bomb, shell, etc to produce frag- used provided part of the cavity would be
mentation or demolition, it is called hurstirzg filled with a small removable chge, known as
(or main) charge. If the chge is without casing, supplementary charge
such as used in detg blast characteristics, it The so-called s@nging charge intended
is called b~re charge and if the chge is within for use with the blast-driven earth rod, Ml 3,
a container, it is called cased charge or as art expl chge which may be inserted into the
con/ined cbarge(if the container is resistant). borehole after the rod has been extracted, is
A small chge of BkPdr or other low expl covered by US Spec MIL-C-13882(Ref 7). The
contained in a ~~base ejection projectile” for chge consists of pellets of Comp B
the purpose of expelling the contents, such as A propellant charge (or powder charge)
smoke canisters, is called base ejecting charge is a given quantity of a ‘tlow explosive’ ‘(such
or expelling charge. A chge used in demolition as BkPdr, colloidal smokeless proplnt$ com-
items is called demolition charge and that posite proplnt or liquid rocket proplnt), which
used for producing craters in earth is known bums under partial confinement in the bore
as craten”ng charge. An expl chge used in of a firearm or in a rocket motor in order to
bombs designed to be dropped or catapulted propel, by the pressure of resulting gases, a
from a watercraft for use against submarines, projectile. If a round of ammo in an artillery
etc is called depth bomb charge. A chge with weapon is “fixed”$ the proplnt chge inside a
a shaped cavity is called shaped charge, cartridge is rigidly fixed to the projectile; if
cavity charge or bellow cbarge(GtBritain). If it is a ‘~semifixed” ammo, the proplnt is in
the cavity of a shaped charge is lined with several bags which are, in turn, contained in a
sheet-metal, it is called lined charge or cartridge case which is loosely attached to the
lined shaped charge. This term should not proj; if it is a “separate-loaded” ammo, the
be confused with the line charge, which proplnt is contained in separate bags which
consists of a chain of several split elongated are loaded directly behind a proj in a breech.
 C 151

A chge consisting of several bags, equal or Charge, Bursting. See under CHARGE
unequal in size, so that range & muzzle
velocity adjustments can be made by increas- Charge, Cased. See under CHARGE
ing or reducing the number of bags( as contrast-
ed with a single-section charge, in which the Charge, Cavity. See Shaped Charge
chge cannot be changed) is called rnultisection
charge. The bag nearest to rhe breech is called Charge, Cratering. See Cratering Charge
base charge and if it produces a normal velocity
of proj, it is also known as normal charge. The Charge creuse(Fr). Hollow or shaped charge
other section(bags), which are intended to
increase the muzzle velocity and range are Charge, Cutting. See under CHARGE
called increment charges. If a multisection
chge is made up of equal wt bags, it is called Charge, Delay. See Delay Charge
equal section charge and if the wts are unequal
-unequal section charge. A charge intended to Charge, Demolition. See Demolition charge
produce full service muzzle velocity is called
full charge, while the chge producing very Charge de poudre(Fr). Propellant charge
high muzzle velocity is known as .@ecial
charge. A chge intended to produce muzzle Charge, Depth Bomb. See under Charge
vel below normal is called reduced charge and
when such chge is used for target practice it Charge, Equal Section. See under Charge
is known as target charge
In certain cases, such as in some US Charge, Expelling. see under charge
howitzers, two types of chges are provided,
one for inner, the other for outer zones of Charge, Explosive. See under charge
fire. The cloth of the bags for the inner zone
is dyed green, while that for the other zone Charge, FIash. See under Charge
white, Accordingly there are green bag charge
and white bag charge Charge, Green Bag. See under Charge
A chge of proplnt which travels along
the bore with rhe proj as burning proceeds is Charge, Hollow. Brit for Shaped Charge
call ed t rav elling charge or Langweiler charge.
For certain large chges, where the individual Charge, Increment. See under charge
proplnt grains are large and it is desired to
make the chge as small as possible, the grains Charge Limit or Limit Charge (charge Iimite or
are placed end to end within the proplnt bag. Charge maximum in Fr; Grenzladung in Ger).
This is known as stacked charge When a chge of an expl is fired in a bore-hole
Refs: I) Anon, “Ammunition Inspection Guide”, of gassy and/or dusty coal mine, the flame
TM 9-1904( 1944), 100,102,104,107,109,115 & 122 produced on expln might ignite the gas(known
2)Ohart(1946), 19,36,123,171-2,188-9, 192,218, as “firedamp”) and/or coal dust if the temp
236 & 239 3) Anon, “Artillery Ammunition”, of flame is above ignition points of gas or
TM 9.1901(1950), 4-9,14-17,35 & 333-53 4) dust, This would cause an expln in mines
Anon, ‘(Ammunition General”, TM 9-1900(1956), resulting in many deaths and in damage to the
33-60, 128-131,142 & 260-62 5)G10ssaKy of mine. Up to the invention of NG expls, BkPdr
0rd(1959), 64-7 6)uS Specification MIL-C-13882 was used, nearly exclusively, in most of the
(Charge, Explosive, Springing for Rod, Earth, coal r.tiaes. The precautions to prevent expls
Blast Driven, M13) of firedamp consisted of using a)’ ‘safety
lamps’ ‘(inyented in 1816 by Sir Humphry Davy)
Charge-amorce(Fr). Primer charge b)efficient ventilation in work area and c)rather
small chges in bore-holes
Charge, Base. See under CHARGE When BkPdr started to be replaced by
NG expls, the number of disastrous expls of
Charge, Base Ejecting. See under CHARGE firedamp increased and this forced some
European countries to inaugurate studies on
 C 152

,causes of firedamp expls. French Govt created limit chge established as 900g(Ref 8,P 238-
in 1877 the Commission de Grisou, but it was & Ref ll,p 418)
not until 1888, that some safety regulations for In England the safety expls known as
use of expls in coal mines were adopted by ‘ ‘Permitted Explosives” were adopted and
the Commission des Substances Explosives. their limit chge was fixed as 280z(793.8g)
These rules were based on recommendations (Ref 8,pp 239-40)
of Mallard & collab, published in MP 2, 355-518 In Germany the safety expls, designated
(1884-1889), under the title of “L’Emploi des as “Wetter- or Wettersichere- Sprengstoffe”,
Explosifs en Pr&sence du Grisou’ ‘(See also were adopted and the limit chge was fixed as
Ref 8,P 229) 450g for gassy coal mines and 600g for dusty
One of the findings of Mallard & collab coal mines(Ref 8,p 242)
was, that in order to ignite firedamp it is h US, the safety expls, designated as
necessary to have the temp of flame produced ‘*Permissible Explosives”, were adopted and
on expln of chge, considerably above the their limit chge was fixed as 240z(680g), for
ignition point of gas. Another finding was that untamped chges(Ref 3,p 587 & Ref 8,p 239)
ignition of firedamp does not take place imme- The test formerly used at the USBur-
diately on contact with flame, but there is a Mines for detg limit charge, was conducted by
r ‘retardation” of as high as 10secs at temp firing unstemmed chges(in original wrappers)
of flame 6500 and lower at higher temps(Ref in amts increasing by 25g, into a gallery
ll,p 438). If during this induction period, the contg air wirh 4% of natural gas and 201bs of
temp of flame is reduced(due to adiabatic bitumirwus coal dust, (100-mesh, fine), until
expansion) to below the ignition point of the maximum amt was found of which 10shots
firedamp, there is no danger of expln. As the could be fired without causing an expln.
flame produced by a small chge is easie: to The temp of gallery atm was 25°(770F). The
cool by expansion, than that of larger chges, gallery consisted of a cylinder 30.48m in length
most European countries and later the US & L93m in diam, built of boiler-plate steel in
adopted the idea of “limit charge”. This may 5 divisions, each consisting of 3 similar
be defined as: “the largest charge at which no sections. One end of the gallery was closed
explosion takes place on firing 10(or 5) shots by a concrete block, while the other end was
into a gallery contg firedamp of approximately closed with a steel plate having in its center
the same composition as encountered in coal a hole 12” in diam with a ring 10.5” ID which
mines’’(Refs 1,3,4 & 8) was made to fit snuggly with the surface of
Investigations conducted in France, the muzzle of the cannon used in shooting
Belgium, England and Germany showed that into the gallery. The cannon consisted of a
although each expl compn has a different limit steel cylinder 91.4cm long, 6 lcm OD &
charge, it is usually in the range of 200 to 21. lcm ID. The natural gas consisted(approx)
900g. Marshall(Ref 2) and Barnett(Ref 4,PP of methane 88.0, ethane 10.8 & nitrogen 1.2%.
132-41) listed compns and props of many Out of 201b of coal dust, 181bs were placed
safety expls, including their “limit charges”. on shelves laterally arranged along the first
In about 1890, Fr Govt, on recommenda- 20ft of the gallery, while 21bs were placed
tion of Mallard & Le Chatelier, prohibited the near the inlet system(for the gas) in such a
use of BkPdr in coal mines(Ref ll,p 403), but manner that all or part of the dust would be
permitted the use of some expls, which were suspended in the 1st division of the gallery
designated as “Explosifs de. Surete” or (Ref l,pp 88-% Ref 3,P 587 & Ref 4,P 123)
“Explosifs Antigrisouteuses”. These were (Not described in Ref 7)
subdivided into “E.xplosifs Couehe” and For description of detns of limit charges,
“ExpIosifs Roche”. For the first , the limit as conducted in Belgium, England, France and
chge was established as 500g with maximum Germany, see Refs 3, 4 & 8
temp of flame(calcd) 1500°; while for the second, According to Pelant(Ref 10), the rests
the chge was 1000g & the temp 1900 °(Ref 4,p conducted in 1930$s at Moravsk~ Ostrava,
122 & Ref 8,p 2381 Czekoslovakia with chges of not “safe”
In Belgium, the safety expls, designated expls ranging betw 200 & 500g, showed that
as “’Explosifs SGP’’(Explosifs S6curitd ignition of firedamp took place after each
-Grisou-Poussi2re), were adopted and their firing. Based on these rests, Pelant came to
 C 153

the conclusion that limit charge is of no Charge, Normal. See under CHARGE
significance
Accdg to Ref 12, the older Russian Charge, pole. See under CHARGE
regulations specified that the maximum chge
per bore-hole in gassy coal mines should be Charge, Propeilent. See under CHARGE
800g. Recent investigations have shown,
however, that ignition or non-ignition of fire- Charge, Propelling, Earth Rod. A chge of
damp by a “safe” expI depends rather on the proplnt in a metal can used to drive ~ metal
conditions at which expln takes place, than rod into earth or shale
on the wt of the chge. In the new Rus regu- i?e/: Glossary of Ord( 1959), 65
lations the chge per bore-hole is limited not
by its wt, but by the depth of the hole. In Charge, Reduced. See under CHARGE
blasting of gaseous coal, the size of the chge
should never be longer than half of the length Charge Section. One of the component parts
of the hole and the remainder should be filled of a chge that is made up of two or more
with stemming(tmping) separate parts
Re/s: I)C.Hall, W. O. Snelling & S. P. HowelI, Re/: GIossary of Ord( 1959), 66
“Investigation of Explosives Used in Coal
Mines”, USBurMines Bull 15(1912),pp 82-9 Charge, Shaped. See Shaped Charge
2)MarshaIl 1(1917), 390-91 & 395-97 3)Marshall
2(1917), 582-606 4)Barnett( 1919), 122-23 & Charge, Single Section. See under CHARGE
132-34 5)Nao~m, EzPIs(1927), 138( Grenz1adung)
6)Nao~m, NG( 1928), 385 7) C. E. Munroe & J.E. Charge, Special. See under CHARGE
Tiffany, “Physical Testing of Explosives”,
USBurMines Bull 346(1931), 49-57(Detn of Charge, Spotting. See under CHARGE
capacity of expls to ignite flammable & expl
atmospheres) 8)Vennin, Burlot & Lecorche Charge, Springing. See under CHARGE
( 1932), 228-51 9)Marshall 3(1932), 187 10)
V. Pelant, Chim & Ind(Paris), Special Number, Charge, Stacked. See under CHARGE
p 901(1933) ll)Pepin Lehalleur(1935), 407=22
12)A.I.Seleznev, Ugol’ 26, No 5, 29-30(1951) Charge, Sticky. See under CHARGE
(Engl translation is available in PicArsn Library
as U39646) 13)Blasters ‘1-jbd( 1952), 26-7 Charge, Supplementary. See under CHARGE

Chargement en comprimé or Chargement par Charge, Target. See under CHARGE

compression (Fr), See Press-Loading, under
Loading of Ammunition Charge, Travelling. See under CHARGE

Chargement en fondu or Chcrrgement par Charge, Unequal Section. See under CHARGE
fusion (Fr). See Cast-Loading, under Loading
of Ammunition Charge, Wedge. See under CHARGE

Chargement en nougat or Chargement mixte Charge Weight Ratio. The ratio of the wt of a
(Fr). See Cake-Loading, under Loading of chge(especially an expl chge), to the total
Ammunition weight of the loaded bomb, shell, etc that
contains the chge. For example this ratio is
Chargement des obus (Fr). Loading of Shells. ca 50Z for GP(general purpose) bomb, ca 70 z
See under Loading of Ammunition for LC(light case) bomb, ca 15% for AP(armor
-piercing) bomb and ca 30% for SAP( semi-armor
Chargement en semoule (Fr). See Slurry Loading -piercing) bomb
under Loading of Ammunition Re/s: I)Glossary of Ord( 1959), 67 2)Encyclo-
pedia, VOI 2(1962), under BOMBS
Charge, Multisection. See under CHARGE
Charge, White Bag. See under CHARGE
 C 154

Charlotte Ordnance Missile Plant. A missile The rifle was eventually modified by Capt
assembly plant, located at Charlotte, North Gras to adopt a center-fire metallic cartridge,
Carolina 1 lmrn caliberjand this weapon remained in use
Re/: Glossary of Ord( 1959), 67 until ca 1874, when it was replaced by Gras,
llmm and in 1879 by Gras-Kropatschek, 1 mm.
Charpy and Izod Tests. These tests, known All these weapons were single-shot and used
also as “’notched beam(or bar) impact tests”, BkPdr as proplnt
have been widely used in US for testing the Re/s: l) W. W. Greener, “The Gun and Its
strength of metallic and plastic materials Development”, Cassell, petter, Galpin & Co,
(including those used in ammo). In both tests Lmdon(1881), 129-31 2) W.H. B. Smith, “Rifles”,
the specimen is struck by a calibrated swinging Vol 2 of the ‘“NRA Book of Small Arms”,
pendulum of a pendulum machine( such as the Military Service Pubg Co, Harrisburg, P a( 1948),
Pendulum-Type Impact Machine, which is 60 & 150 3) Encyclopedia Britannica 5( 1952),
briefly described in Ref 2,p 60) and the energy 312-13
absorbed by the fracture is detd. Both tests
employ low striking velocities, such as ChatelIerauIt Machine Gun(FusiI-mitraill eur
17.5 ft/sec for the Charpy and 11.5 for the Mod$Ie 1924, in Fr). A weapon also called
Izod test. In the Charpy Test, the notched bar automatic rifle, adopted in 1924 by the French
is placed betw two supports (without using Army. It used 7. 5mm rimless cartridges and
clamps), with notch equidistant betw them its magazine capacity was 30 cartridges.
and is struck by the pendulum on the side It was manufd at the Chatellerault Arms
oPPoslte the notch; whereas in the Izod Test, Plant. Later models(1934- 1939) intended for
the specimen is held in a vise as a cantilever use in tanks, armored cars, airplanes used
bar with center line of the notch on a level larger capacity magazines. The so-called
with the top surface of the clamping device ‘(fortress model”, used during WWH in Maginot
and the specimen is struck by the pendulum Line had a magazine holding 15o rounds.
on the notched side 22mm above the edge of Chatellerault also furnished an aircraft
the clamp(Ref 2)( See also Ref 4). The testing version which on tests fired 1300 rounds per
procedures are given in Ref 3 min
Gibson(Ref 1) investigated both methods Re~s: l) G. M. Chinn, “The Machine Gun”, US
for testing steels, such as used in manuf of GovtPtgOff, Washington DC, Vol 1( 1951), 40 I-6
shells & gun barrels and gave preference to 2) M. Lefort, MAF 29, 800( 1955) 3)’W.H.B.
Charpy Test Smith & J. E. Smith, ‘tSmall Artms of the World”,
Re/s: I) W. A. Gibson, PATR 238( 1932) la) Stackpole, Harrisburg, Pa ( 1960), 139 & 392
Hayes(1938), 138 2)M.Het~nyi, ‘“Handbook
of Experimental Stress Analysis”, Wiley, Chatellerault Arms plant (Manufacture Nationale
NY( L950), i6 & 60-1 3)ASTM stds(1961), Pt 3: d’Armes de Ch2tell erault). French Govt
A327-54,pp 75-8 & E23-60,pp 79-93 4)w. Arsenal, Iocated at Ch2tellerault(Vienne),
Spiith, “Impact Testing of Materials”, Gordon manufg various small arms, including machine
& Breach, NY(196 1), 79-85; translation and guns. It was founded in 1819. A good historic
revision by M. E. Rosner of “Der Schlagversuch description is given in Ref 2
in der Werkstof fpriifung”, Gentner Verlag, Re/s: I) W.H. B. Smith, “Rifles”, Vol 2 of
Sruttgart( 1957) “NRA Book of Small Arms”, Military Service
PubgCo, Harrisburg, P a( 1949), 150 2)M.
Chassepot Rifle. A breech-loading rifle Lefort, MAF 29, 781-800(1955)
invented in 1866 by A.A. Chassepot(1833- 1905)
and adopted ca 1869 by the Fr forces under Chauchat Machine Rifle, Model 1915 (Fusil
the name of ‘* Fusil mod~le 1866”. It was a -mitrailleur Chauchat-Suterre, in Fr)(call ed in
bolt-action weapon, which was superior to England “Chauchard”). A cal 8mm weapon
Ger “needle-gun” invented by N. Dreyse ca used during WWI by French troops. From Dec
1838. Although “’chassepot” had the defect 1917 to Apr 1918, nearIy 38000 Chauchats were
of employing soft paper, self-consuming shipped to US to equip nine combat divisions
cartridges, it was used rather successfully before sailing to Europe. Some of these
during the Fran co-Prussian War of 1870-71. weapons were altered to caliber .30
 C 155

Refs: l)G. M. Chinn, “’The Machine Gun”, sidiary of the Soci6t6 Anonyme Suisse
US GovtPtgQff, Washington, DC, Vol 1( 195 1), d’Explosifs, Liestal, near Basel, Switzerland
238-42 2) W. H. B. Smith & J. E. Smith, ‘“Small has also plants located at Torano(Carrara),
Arms of the World”, Stackpole, Harrisburg, Borgofranco(Ivrea) and Cinzano Torinese(Ref
Pa(1960), 127 & 390 35). Besides France, Italy and Switzerland
(Refs 21,27,31 & 35), Cheddites were also
Chauvet Powders, patented in 1882: a)K manufd in Germany (Refs 2 I & 27), Australia
chlorate 95.2 & K ferr ccyanide 4.8% and b) (Ref 18), Russia(Ref 20a), Belgian Congo
K chlorate 90, K ferrocyanide 5 & sugar 5% (Ref 28), Algeria(Ref 28), Tunisia(Ref 28) and
(Compare with Cauvet & Baron Explosives Finland(Refs 33 & 35). Accdg to M4dard(Ref
listed in Vol 2 of this Encyclopedia and with 28), the name of the firm manufg Cheddites
Polveri Baron e Cauvet in Ref p,394) in France is the Soci~t~ G4n6ra1e d’Explosifs
R e/: Giua, Trattato 6( 1959), 394 “Cheddite”, main office in Paris and the
plant at L amarche-sur-satme(cfke d’Or). This
CHEDDITES OR STREETITES Company owns also the plant in Algeria( at
(Street Explosives) Bell efontaine) and in Tunisia(Mancuba).
(Cheddites, Explosifs Street, Explosifs O or Cheddites were al somanufd in Spain(Ref 26,p
Explosifs du type OC in Fr; Cheddite in 349)
Ger; Chedditi in Ital; Chedditas in Span; Chlorate Cheddites may be subdivided
Sheddity in Rus). Cheddites are special into nongelatin- and gelatin- types. The non
types of chlorate(or perchlorate) explosives. -gelatin-type Cheddites are in the form of
‘The main feature of Cheddites is that the soft grains, white or yellow in color, unless
grains of chlorates(or perchlorates) are coated they have been artificially colored by some
with liquid(or pIastic) materials in order to oil-sol dyes in order to distinguish one type
render the grains less hydroscopic and less from another. They are readily compressible
sensitive to mech action( such as impact or and in order to obtain the full expl power
friction) their density should be carefully controlled.
Historical. Explosives now known as If the d is low the max power is not developed,
“Cheddites” were invented in 1897 by Street whereas very high compressions lead to
(Ref 1) and in 1898 were patented several difficulty in detonation. These expls are
varieties of the original compn. One of the relatively insensitive to shock and friction
formulas contained nitronaphthalene picrate, at RT and burn, when unconfined, more or
called in Fr “picronitronaphthalene”. At less rapidly without any tendency to, expIode,
about the same time the Chemische Fabrik even when fired in large masses. Heating at
Griesheim in Germany patented a similar exPl 120° for an appreciable period causes no
contg nitrotoluene picrate( called in Fr decompn, but at 2000 the oil in Cheddite
“picronitrotoluene’ ‘)( See Ref 5,p 740). Manuf decomposes, part of the nitrocompds volatilizes
of these expls under the name of ‘tExplosifs and the whole mass darkens. Heating of
Street” began ca 1898 by the Soci6t6 Berg*s, Cheddites in small quantities to 250-65° causes
Corbin et Ci e at Chedde, Haute Savoie, France deflagration. Densities of compressed mat-
and certain varieties were admitted to Belgium. erials average 1.3- ‘1.4; power(by Trauzf test)
They were also exported to England where slightly below that of TNT, but their brisance
they were authorized since 1900 under the name (by Kast’s formula or by Cu crusher test) is
of ~’Cheddites”, called so because they were only 30-50% of TNT, due to the low detonation
manufd at Chedde. As far as is known, this velocity, 2300 -3200 m/sec(as detd by the
plant is still in existence(Ref 5,PP 139 & method of Dautriche). This rate depends not
740-1 only on compn but also on density. It increases
A subsidiary of the French firm was with the d up to a certain point(optimum density)
established in ’001 in Salviano, neat Livorno, and then decreases very rapidly. For example,
Italy(Ref 7). Accdg to “Dr Omero Vettori(Ref one of the Cheddites developed the rate
35), it is likely that this plant is now one of 2283m/sec at d 1.07, it increased to 2901 at
the plants belonging to the Societ?i Italiana d 1,17, dropped to 2451 at d 1.14 and failed
Esplosivo Cheddite with the main office at to detonate at d L5(Refs 13,15,20 & 23)
Torino. This Company which is now a sub- Information in the literature on expl
 C 156

props of Cheddites is rather scarce, but non-hygroscopic( Refs 1,2,3,4,5,7,11,13,14,15,

whatever is available is shown here in Tables 17,20,20 a,23,26 & 30)
or in Notes to Tables Some Cheddites patented by Street(Ref
None of the Chlorate Cheddites can 2), were prepd by coating K chlorate with
contain any Amm salt, because double decompn ‘qsulfurated oil”, which was obtained by
might take place with the formation of dangerous heating to 180° ca 10ps of sulfur in 90ps of an
Amm chlorate. Cheddites contg K or Na oil, preferably I ins eed oil. Another variety
perchlorares are more stable and less reactive patented by Street(Ref 4) was obtained by
than those contg K or Na chlorates. Amm incorporating K chlorate with varying relative
~rchlorate may also be used, provided chlorates quantities of a mixt of charcoal and PA with
are absent. Na chlorate is more hydroscopic pitch, tar or vegetable oil
than K chlorate but it is more economical and For gelatin-type Cheddites, the nitro-
contains more oxygen per unit wt(Ref 24,p compds( see under manuf of non-gelatinized
359)( See Tables 1,2 & 3) types) are mixed with NC & NG and heated to
The gelatin-type Cheddites are plastic ca 40° until the mass becomes uniform. Then
type expls which do not harden in storage. a finely powdered chlorate is added and coating
They were developed in 1911 by C. Rubins and is conducted with stirring, but without raising
manufd by the Cheddit & Dynamit AG, Liestal, the temp(Ref 23)
Switzerland and then in other countries. These Detailed description of manuf of French
expls are not ve~ powerful, but their brisance Cheddites as it was done at the Poudrerie de
is superior to any AN expl. They are very Vonges is given in the book of Vermin, Budot
effective for work in galleries, especially with & L6corch4(Ref 20,pp 54 1-3). A good description
humid and not too hard rocks(Ref 21,p 3 13; Ref of its manuf in Spain is given by Vivas,
27,p 90; Ref 30,p 180 & Ref 31,p 118)(See Feigenspan & Ladreda(Ref 26,pp 350-11
Table 3) Compositions o/ Cheddites. Some formulations
Manufacture of Cbeddites. For non-gelatinized of Cheddites contg azobenzene are Ii steal in
types the following procedure may be used: Vol l,p A647-L of Encyclopedia and some
One or several expl compds [ such as MNN, examples of Cheddites contg castor oil are
DNN, MNB, MNT, DNT, liq TNT(Drip Oil), P A given in VO1 2, under Castor Oil
azo- or azoxybenzene, et c~, are dissolved in The first Cheddites or Street Explosives
a heavy oily substance(such as castor-, linseed-, studied and approved for manuf at the Poudrerie
olive-, or pertoleum oil , paraffin, wax$ fat$ de Vonges by the French “Commission des
vaselin, pitch, tar, resin or plastic material) Substances Explosives”, beginning 1897, had
by heating the mixt in a steam-jacketed. the compns listed in Table l(Refs la$5, 13,15,
enamelled iron parI at temps of 65-80°. When 20 & 24)
the mass becomes homogeneous, it is allowed Table 1
to cool to ca 55°, and then preheated(to ca Composition I II 111
500), dry and finely pulverized chlorate(or K chlorate 75.0 74.6 80
perchlorate) is gradually introduced, while Picronitro- 20 - -
naphthalene
stirring with a wooden spatula. As soon as
it becomes evident that the particles of 5.5 12.0
powder are uniformly coated with oily mixt, Starch 14.9 .-
the slurry is transferred to another building Castor oil 5.0 5.0 8.0
where it is poured onto a flat wooden surface ~~s~:~kity Lower than that
and rolled into a thin layer for cooling to f~GN~5 l&Dyn ami te
Bri sance
30-35°. Then the resulting solid mass is Rate of i Ieselguhr
broken by means of a wooden roller into detonation 25%)
grains and these are passed thru a screen, to Note: Picronitronaphthal ene or Nitronaphthalene
remove the very fine particles. Finally the Pi crate is an equimol ecular combination,
grained Cheddite is made into cartridges by Cl ~H7(N02).C6H20H(N0 )3, mp 71° [See
pressing in wooden molds from which it is Jovinet, MP 23, 37( 1928)7
transferred to paper cartridges. Cartridges contg Prior to WWI and probably up to WWII
Na chlorate Cheddite should be dipped in Cheddites listed here in Table 2 were author-
molten paraffin or wax in order to render them ized in France and large quantities were
 C 157

exported to Belgium, Engl.an d ~d other ticrn(1932) of the book of Vennin~ BurIot &
countries. It is probable that most of these L 4corcht5(Ref 20)
Cheddites were manufd at the time of publica-
Table 2
French Chlorate Cheddites or Explosifs O
On” 1 On” 2 On04 On05 On05 On” 6 f.)nG’7 0n08
.. ---- . .. -. ----- .. . . . .— . . ... .-— -—
Composition 41 —..
-... 60tis
-. 60bi SM —. -., ...-— bis A
--- B —<C’ —>
K chlorate -_ 90
80 80 79 90 ~89-
Na chlorate -- 79 79 -- 90 90
MNN 12 13 1
-_ ---
DNT(cryst,mp 67-9°) 2 15 16 2 -- -
TNT -- 14 -- -
Castor oil 85 5 55 ----
-- -_ 7 757 10
Paraffin 10
-- -_ 343
Vaselin
-- -_ 3 -- -
Heavy petr oil
-_ -_ 2-
Pitch, tar or rosin

Notes to Table 2 are listed below Table 3 and Notes to Table 3 are on p C 158
Table 3
Various Chlorate Cheddites (Non.gelatin Types)
French Cheddites British .SwissGerman
60N 60N On05 0n014 0n014
Composition 41 60
—— (older) (newerj 7
?60N&~
—— —.— .-. . A. L. 2. -
K chIorate 7980 - - - - _ 90 - ‘78090
73
Na chlorate -- 80 75 77 87.7 87.5 - 89 79 -79--
MNN ___
DNT
TNT --- .- ---
16 16 2 (!q)- T-
-- 145-
Castor oil 665 5 - O*9 - - - 54-
5
Resinous oil --- -_ _ -- -( 5 ----
Paraffin --- -_ 7.1 800 10 11 -_ ---
Heavy petr oil --- -_ _ --- -_ -- 10
PA 2 ----- -- -- ---
Starch --- --- -- - 6 ---
Sawdust --- -_ _ --- --- 1-
Power(PA= 100%) 87 80 80
References 11, 11, 11, 11, 29, 29,. 29, 13, 13, 14, 14, 27; 21, 21,
p128plll P124 P128 P212 p210 p212 P496;P496; p 167 P168p87;p314p314
21 24, 24, 31
p314 P361 p361 pl13

Notes to Table 2:
A) Follo wing properties are given for Cheddite 23.8 x 106( TNT 86,1 x 10s), brisance by Cu
On 02 60bi sM(modi fi 4e) by Sukh arevskii & cylinder crusher test 1.4mm(TNT 3.6), sensitive-
Pershakoff(Ref 20a): density, g/ml 1.4(TNT ness to friction by rubbing in porcelain mortar
1.59), heat of formation+ 666caI\g(TNT +70.5), exPlodes(TNT does not), ~ensitiviness to
heat of explosion 1185crd/g(TNT 950), volume impact, using 2kg weight 30cm(TNT 60cm)
of gases of expln 337 l/kg(TNT 69o), ignition B)M&dard(Ref 29,p 2 10) gives po wer(CUP) for
(defIagration) temp ca 260°(TNT ca 3000), On” 5 86% of PA and for 0n08 78%
max temp of expl 4500 °(TNT 22800), detonation C) Cheddites On 06 were used during WWI for
rate 3000misec(TNT 6700), power by TrauzI test military purposes under the names of Min61ite A,
255cc(TNT 285), brisance by Kast’s fo~ula Min&lite B and Mine?lite C. The best known was
 C 158

MindIite B which wasused for loading grenades reduction of cost, but it also made the Cheddites
and mines. A similar Cheddite contg 90% of Na more hydroscopic. This disadvantage can,
chlorate instead of 90 of K chlorate was used in however, be overcome by waterproofing the
grenades and trench mortar s(Ref 24,p 361) containers(paper cartridges) with molten
D) Accdg to Vermin et al(Ref 20), the most paraffin. More serious disadvantage of Na
pcpular type of Cheddite used in France after chlorate Cheddites is the proximity of
WWI was on 05 and the next in popularity was “optimum $~ density (at which the expI performs
@ 08 the best) to “limite density ’’(density Iimite’$
E) Accdg to Giua(Ref 32,p 398), a variety of in Fr) at which the expl becomes insensitive
Cheddite, prepd by coating the grains of K to initiation
chlorate with a mixt of linseed oil and an amide Older French Cheddites On”>, 0n06B,
was patented in 1903 by Brown & Moore for use 0n08 &on” 14(s.ee Tables 2 & 3) had low
as a smokeless propInt “limite” or “optimum” densiti es, low deton
There were many other Cheddites used velocity and low power(wP ). As their oxygen
prior to WWII and several of them are listed balance was positive it was presumed that by
in Table 3 bringing it closer to zero, (such as by increasing
the amt of DNT), it wouId be possible to obtain
Notes to Table 3: more powerful expls. This, however, did not
A) Cheddite known in France as P was designat- achieve the purpose, because the addn of
ed in Germany as Miniersprengsto//. It was used extra DNT increased. the density of the compn
for demolition work, such as destroying bridges, above its ~‘optimum” value and rendered it
RR switches etc(Ref 27,p.91) sometimes insensitive to initiation. In order
B) Barnett(Ref 15,p 109-11) gives for Cheddite to avoid this, it was proposed to reduce’’d~’ by
P detonation velocity 3565m/sec at d 1.45 and incorporating some light materials, such as
for Cheddite S 2940 at d 1.45. He also lists cork flour or sawdust( see expls 55-CSE- 1948”
Cheddite Type 604: K chlorate 75, MNN 10 & and 58-CSE- 1948 in Table 4). These expls
DNT 15% with deton vel 3156m/sec at d 1.48 were slightly more powerful than older type
C)To the list of Brit Cheddites may be added Na chlorate-DNT Cheddites, but their manuf
Colliery Cbeddites: K chlorate 76.5-79.5, MNN was more tedious because it had to be con-
15.5-14.5, DNT .2.5-1 .5, castor oil 5.5-4.5 & ducted in two steps, using two different bldgs
moisture up to l%(Ref 14,P 279) in order to avoid explns due tosimultaneous
D)Ger Cheddite designated as 2 was used, presence of dusts of a fuel and of an oxidizer
under the name of Miedziankit in Ger-Polish in the same bldg. In the 1st bldg liq DNT was
mines(Ref 21,p 314; Ref 27,p 91; Ref 31,p 118) mixed with cork flour or sawdust and the
Accdg to M6dard(Ref 29), Cheddites are paste transferred to the 2nd bldg where powdered
known now in France as Explosi/s OC (or Na chlorate was incorporated
Explosifs 0) and they are still in demand in The CSE also conducted research on
mining and quarrying operations. Because Gelatin-Cheddites, which were already known
chlorates(and perchloratesj require much in Switzerland and in Italy(See Swiss & Ital
electric energy for their manuf, the Cheddites Gelatin-Ch eddites in Table 4). A corresponding
are rather expensive and they are gradually French formulation, known as On 018 was
being replaced by cheaper nitrate expls(mo stly really no improvement over Swiss & Ital types.
based on AN)$ known in France as Explosi/s It was difficult to detonate unless detonating
Nitrat6s or Explosi/s N. In order to make cord was used. Much more powerful “Gelatin
Cheddites less expensive, so that they might -Cheddites” were obtained when Na chIorate
compete with Explosifs N, research has been was replaced by Amm perchlorate and when
undertaken in France, mostly at the laboratory P ETN was incorporated(see below under
of CSE(Comission des Substances Explosives). Percblorate Cheddites)
As a result of this research some improved and Accdg to Dr Ornero Vettori(Ref 35), the
less expensive formulations were developed. following Cheddites have been manufd by the
One of the economic improvements was the Societh Itrdiana Esplosivo Cheddite at the
replacement of crystalline DNT(mp 67-9°) Salvi ano(Livorno) plant: a) Cheddite OS Extra
with cheaper, crude( called 0‘liquid’$) DNT(mp b)cbeddzte O Extra c) Cbeddite O Extra B
50-8°)(Compare expls of Table 2 with On05A d) Plastigel I and e) Plastigel /[(See Table 4),
and 0n014A of Table 3). Use of Na chlorate Their compn & props arra given by Dr Vettori.
in lieu of K chlor’kte al so contributed towards Stability of Plastigel is y30mins at 600
 C 159

Table 4
Newer Types of Chlorate Cheddites
French Italian Cheddites
Composition and 55 58 OS Swiss & Itsl French Italian
Some Properties -CSE -CSE Extra Extra Extra Gelatin Gelatin Plasti~;ls
-1948 -1948 B Cheddites Che-ddite I
—. -tir*
Na chlorate 74 74 90 79.0 8T6 75 70 . =.0 fio
DNT(liquid) 23 23 - 16.0 - 23.8 23.5 19.0 19.7 19.7
Sawdust 3- (@l) _ - - - - -
Cork flour 3 ------ - --
NG -- - 5.0 5.5 - -
Collodion cotton - - - - - 1.2 1.5 1.5 1.8 1.8
Castor oil - - 5.0 --
Paraffin 7 5.0 --
Vaselin 3 2.4 --
PETN 6.5
TNT 10.0 6.5 -
Oxygen balance % - - +6.o3 +3.9.0 +4.32 +’4.4
Density, g/cc - - ca 1 ca 1 ca 1 1.9 2.0 ca 2
Detonation - - 3000 3200 3200 3600 -
rate, m/s
Power(PA 100%) 93 89 80 94 85 83 83 83 108 -
Impact test, - - >18 28 >16 24 -
cm, 2kg
References 29 29 35 35 35 21 & 30 21 29 35 35
Percblorate Cbeddites are those based on In Table 5 are listed some typical
perchlorates, such as of K or Amm. Mixts P erchI orate Cheddi tes. Two French plastic
based on KC104 are more powerfd, more Cheddites, designated as Sevranite no I and
stable and less sensitive to ignition, friction Sevranite 72°2 were developed at the laboratory
and percussion than corresponding mixts contg of CSE after 1$)46. They are much more powerful
KC103. Mixts contg NH4C104 are even more than any previously known Cheddites(CUP is
powerful than those contg KC104 and they are 142% PA for no 1 and 138 for n02) and their
suffi ci endy insensitive to be handled with detonation velocity is ca 7000m/sec at d 1.55
safety. Some Perchlorate Cheddi tes were used (Ref 29,PP 218-19)
for military purposes Table 5
Perchlorate Cheddites
Brit German French Bel-
French Blas- Mili- ;erc$lora;ts Swed Sevranites
Composition I .— II 111 — tine t ary
—. —. Territ nol n02
—.
Ammperchlorate =2 50 88-9060 --- 43 31 42 43
K perchlorate --- - 56 68 35 34 -
Amm nitrate --- . 10 42 48 -
Na nitrate 30 — 22 --- 28 32
MNN --- - 121 ---
DNB --- - 32 -- - -
DN T 1315 -- --
--- ;16 :14 12 127,8
TNT 11 -. 15
Castor oil 5 5— - --- _ .
Paraffin - 12-10 7 ___ -
NG --- - 44--
Collodion cotton - - - - --- 1.2
Woodmeal --- _ 156- —
PETN --- . --- - 48 42
Plasticizer - - - - --- - 18 16
AI powder --- _ --- _ 3 - 10
References 8 8 21 21 21 21 21 21 21 29 21
P316 P316 P316 P316 P316 CY316 D~16 Pp 218-19 P316
 C 160

Notes to Table 5: G)Belg Yonckite(spelled in Ger Jonckit) was

A) French expls I & II were designed to be used used for military and industrial purposes
for industrial purposes, while III was used H) Detonation velocity for French I 4020mr sec
during WWI under the name of Perarnmon for at d 1,04, and for II 3361m/sec at d 1.04
filling bombs Uses of Cheddites. Although Cheddites were
B)Brit f31astine was used for blasting operns, originally designed to be used for industrial
including military purposes, some of them were used during WWI
C)Ger Military Cheddite was used during WWI for military purposes, such as demolition work,
for cast-loading 1and- and sea-mines loading bombs, grenades, mortar shells and land-
D)Ger Perchloratits were used for industrial & sea-mines(See also Notes under Tables 2,
purposes 3&5)
F)Fr Sevranites, use is unknown

R efs: I) E. Street, EngP 9970( 1897): FrP Amm perchlorate Cheddites) 27)Stettbacher
267407( 1897); JSCI 17, 375( 1898) (Expls obtained ( 1948), 87 & 90- l(Compn & some props of
by coating the grains of K chlorate with Cheddites manufd in Switzerland and Germany)
nitrocompds dissolved in oils by heating at 28)L. M4dard, MP 32, 210-12[ 1950) (Cheddites
40-60°, with stirring followed by cooling) la) grains of K chlorate with CCsuffurated oil”)
CSE(Commi ssion des Substances Explosives), 3) E. Street, EnglP 13724(1898) & JSCI 17, 488
MP 9, 144( 18Y-8); ] 1, 22(190 1) & 12, 117 & ( 1898) [ Expls prepd by coating the finely
122( 1903-4) 2) E. Street, EnglP 12760( 1898) & pulverized alkaline chlorates or perchlorated
JSCI 18, 400( 1899)( ExpIs prepd by coating ( with or w/o addn of carbonates or hydrocar-
13)Marshali 1(1917), 380-2(Some Cheddites & bonates) with and “oily substance prepd by
their manuf and 2(1917), 49@Some Cheddites & dissolving at 65 to 100° nitrocompds and/or
their props) 14) Colver(1918), 167-9, 279-80 & azo-, azoxy-, amidoazo- or ami doazoxy-
640(Some Cheddites & expl props); 279( Manuf) benzene in an oil (such as Iinseed, olive,
15) Barnett( 1919), 109-12 (Various Cheddites petroleum oils) ] 4) E; Street, EnglP 24468
and Fops) 16)MarshalI, Dict( 19 20), 2 I(Two (1898) & JSCI 18, 1051( 1899) (An expl consisting
types of Fr Cheddites manufd after WWI) of powdered KC103 coated with pitch, vegetable
17) Ullmann 4(1929), 788, under Explosivstoffe oil or tar and mixed with powdered charcoal
(In new edition it wiH be listed under and PA) 5) Daniel( 1902), 134 & 740-4( Compns
Sprengstoffe) 18)R. J. Lewis, “cReport of the of various Cheddites and their prepn) 6)csE
Chief Inspector of Explosives of Victoria (Commission des Substances Explosives),
(Australia) for 1929”, Mel bourne( 1930) MP 13, 144-8 & 282( 1905 -6)( Compn & props of
(Cheddites as authorized expls in AustraIia) Cheddite 60bis & 60bisM)(M stands for ctmodifi6e”)
19)Marsha11 3( 1932), 153 & 155( Compti & 7) E. Bravetta, SS 1, 125-7( 1906) (Manuf of
props of Cheddite 60M) 20) Vermin, Butlot & Cheddites 41, 60 & 60bis at Salviano plant in
L @corch4( 1932), 539-46(Cheddites, calI ed d so Italy) 8)CSE, MP 1A 192-5 & 206-33( 1906-7)
Explosifs Street or Explosifs O) 20a) (Cheddites based on Amm perchlorate) 8a)
Sukharevskii & P ershakoff(l 932), 150 & 198-201 Gody( 1907), 267-8 9)H.Dautriche & E. Burkard,
(Manuf & props of Cheddites) 21)Stettbacher SS 4$ 204-7 & 224-8( 1909) (Prepn & props of
( 1933), 309- 15( French, Swiss & German Cheddites listed in Ref 8) 10)CSE, Mp Is,
Cheddites) 22) Pepin Lehalluer( 1935), 344-9 135-7( 1909 -10)( Props of Cheddite proposed by
(French Cheddites) 23) Thorpe 2( 1938), 525 Bergks, Corbin & Cie:Na chlorate 75, DNT 19,
(Compns, manuf & props of various Cheddites) MNN .1 & castor oil 5%) 1 l) Escales( 1910),
24) Davis(1943), 357-60 & 365-6 (Various 110- 142( Chlorate Cheddites) & 163-84( Perchlorate
Cheddites) 25) P4rez Ara( 1945), 207-8( ~ed&tes) Cheddites) 12)H. Dautriche, Mp 16, 66-8s
26) Vivas, Feigenspan & Ladreda 2( 1946), 211-12 & 224-9(191 l-12)( Ched~tes with NaC103)
349-51 (Compn, manuf & props of K chlorate and

—
 C 161

manufd in France before WWII under the names nitrocompds by various coIorimetric procedures.
of Explosi/s du type OC or Explosi/s cbloratt?es In testing for PA a small part of the residue
were of high quality at comparatively low is treated with w and if the color of Iiq turns
price, especially those contg Iiq DNT. M4dard yel, some KCN soln is added. If the color turns
gives compn of several expls of this type and purple-red, the presence of PA may be considered
lists the pl ants manufg them) 29) L. M.4dard, as proved. TNT is recognized by a deep purple
MP 32, 215 & 218-22( 1950) [Compns and some -red color produced when an al coholic or acetonic
props of modified Cheddites developed and soln of evapd ether(or benz) extract is treated
tested during 1948-1949 in laboratories of CSE with Na or K hydroxide. Under the same con-
(Commission des Substances Explosives)] ditions, DNT(if free from TNT) gives a blue
30)B elgrano( 1952), 179-81 & 184( Compns, props color. If TNT is also present the blue color of
and methods of manuf of several Ital Cheddites) DNT is masked by purple-red color of TNT.
3 l)Stettbacher( 1952), 113 & 117-18(Swiss Heating by direct flame of the test tube contg ca
Cheddites manufd by the Cheddite & Dynamit 0,5g of residue and 6mI of 25% alc NaOH soln
AG at Liestal) 32)M.Giua, ‘ CTrattato di causes, in case of TNT, sym-TNB, or Trinitro-
Chimica Industrial”, UTET, Tori no, Vol 6 metaxylene(TNX) evoln of ammonia, leaving the
( 1959), 396( Compns, some props of Cheddites, soln colored intensively brn-red. Nitronaphthalenes
types 41, 60bis & 60bisM; also of two Amm also evolve ammbnia, but DNB, 2,6-DNT and
perchlorate Cheddites) 33)1. Huhtanen,
MNT do not, while 2,4-DNT does it only after
Explosivst 1960, 189-94 (Cheddite-type expls prolonged heating
used in Finland) 34) IL K. Andteev, Explosivst
TNB, TNT and TNX, dissolved in acetone)
1962, 229(Some props of Cheddite Type 60) develop dk-red color on adding a few drops of
35)Dr Omero Vettori of Societh Italiana ammonia. This reactio~ can also b? used to
E splosivo Cheddite, Via Cernaia 15, Torino, distinguish betwetm a, @ & y-TNT’s, which
Italy; 1etters of Nov 24, 1962, Jan 10, 1963,
give correspondingly. dk-red, green and blue
Feb 2, 1963 and Match 7, 1963 colors. If *’Drip Oil’‘(mixt of crude DNT &
TNT) is present the color with ammonia is red
Cheddites, Analytical Procedures. at the beginning, but, it turns violet on standing.
Qualitative Tests. For Cheddites contg a
MNB and MNT do not produce any color when
chlorate, binding material s(paraffin, vaselin, treated with a caustic or ammonia, but their
castor oil, etc) and powdered coal, a sample presence in Cheddites can be detected by bitter
( 10-~5g) is heated for lhr, under reflux, with almond odor (FLef l,pp 137-8)( See also under
ether(or benz), the extract filtered and evapd Quantitative Tests)
to dryness. It leaves as deposit the binder.
when TNT is present in mixt with DNT,
The non-extractable material is treated with
it is very difficult to detect DNT by blue color
hot w to di SSOIve the chlorate, thus leaving coal
produced on contact with Na or K hydroxide,
as residue. The aq soln is evapd and 0,2-0t3g
beca~lse the red-violet coIor produced by TNT
of solid is heated in a test tube. Evoln of
is very intense ald it masks the blue color of
oxygen, manifested by burning with bright
DNT. For rapid colorimetricdetectionof DNT,
flame of a glowing wood splinter inserted into
in presence of TNT a method developed during
the neck of the test tube, indicates the
WWII at Keystone Ordnance Works, Meadville,
presence of a chlorate(or perchlorate). The
Pa is recommended. The procedure is based
residue after extraction with w is examined for
on the fact that DNT is practically irtsol in
coal by burning a small portion o n the tip of a cold coned soln of Na suifite(known as
metallic spatui a. For Cheddites contg, in lieu sellite), while TNT is very sol. It is
o f coal, some nitrocompd(such as a nitro= described here because Ref 3, where the
naphthalene, nitrobenzene, nitrotoluene or PA),
method originally appeared, is now out of print
the residue(binder) after ether(or benz) extraction Procedure: Triturate in a small mortar ca lg of
is tested for chlorate(or perchlorate), as sample(in which the presence of DNT and(or
described above, but one-half of the evapd
TNT is suspected) with a few mls of CC14, allow
extract is treated in cold with 10% Na or K
to settle and decant the extract into a small
hydroxide. This dissolves nitrocpmpds leaving ieparatory funnel. As soly of DNT in CC14 is
fatty substances as residue, The other half ca 3.5% -and of TNT only 0.7470~ this treatment
of evapd ether(benz) extract is tested for
will dissolve the bulk of DNT, leaving a large
 C 162

proportion of TNT undissolved. Shake the sample(in a flask) with severaI small portions
exti.act in a separator funnel with an equal vcd of hot w, decanting the soln each time into a
of 11% sellite soln slightly acidified with tared, small, sintered glass filtering crucible
Hz S04. AHo w to settle and remove the bottom of medium porosity. Any residue in the flask
layer(soIn of DNT in CC14) to a small beaker. should be transferred quantitatively to the
Discard the red upper Iayer(sellite with the crucible and the latter washed with hot distd w
TNT decomposed by treatment) and transfer the i )Collect the filtrate and washings, cool them
CC14 Iayer back to the funnel. Repeat once or and transfer to a iOOml vol fl. Add dist w to
twice the treatm eat using fresh portions of the mark j )Pipette out a 100ml aliquot into a
sellite and test the CC14 soln for the presence 500ml beaker and add 100ml of 5% AcOH soln
of DNT. For this, place 2 drops of the soIn into contg IOg of n“itron base. Separate the resulting
the hollow of a porcelain spot plate, add 5 ppt of nitron chlorate(or nitron perchlorate)
drops of freshIy prepd coned KOH soln in by filtration thru a sintered glass crucible ,
1:1 alc-acet and observe the color. BIue or a which is not the same as in opn h k)Wash
blue with a pinkish tinge(if TNT was not com- the crucible and contencs with 75- 100ml of 1%
pletely removed by sellite) indicates the AcOH soln, dry, cool and weigh l) Calculate
presence of DNT. Other reagents, such as the percentage of chlorate(or perchlorate) by
diethylaminoethanol, may be used. This colors multiplying the wt by a factor, which is
TNT deep violet and does not color DNT if 0.3092 for KC103, 0.2686 for NaC103, 0.3360
used in neutral media. but colors it blue-green for KC104, 0.2970 for NaC103 and 0.2849 for
if alkali is present NH4C104 m) Dry the crucible with residue
DNT may also be detected and separated (See Opn h) at 100-10°, cool and weigh. This
from TNT & MNT by chromatographic methods, residue might be carbon, sawdust> cellulose>
as described in Refs 2,5 & 6 collodion cotton, etc n) Determine, if required,
Quantitative Tests for Cheddites: a) Extract other props of the Cheddite, such as moisture,
wirh ether for 6-7hrs in a Soxldet(or other acidity (or alkalinity), thermal stability> density~
extractor) a ICI.Og sample and transfer the brisance, power, detonation velocity, etc(see
extract to a tared beaker b) Evap the ether also Ref l,pp 138-9 & Ref ll,pp 470-1)
at 60 °(3-4hrs) and leave the beaker overnight Perchlorates in Cheddites may also be
in a desiccator with coned sulfuric acid. Weigh detd by methods similar to those used in
the beaker to obtain the wt of ingredients, such analysis of composite proplnts, as described
as nitrocomps, vaselin, castor oil, etc c) Remove in Ref 4
from beaker a 0.3-O.5g sample(accuratelY Quantitative Determinations o/ DNT, MNT and
weighed) and determine its nitrogen content TNT in Cbeddites. As drip oil(mixt of impure
by Kjeldahl method, as modified by Williams DNT, MNT & TNT) is often used for manuf of
d)If presence of PA is suspected, treat Cheddites, it is necessary to know how to
(with warm di std water) about one-half determine these ingredients
(accurately weighed) of the material left in the The following two methods, taken from
beaker; fiIter the extract and treat the filtrate Ref 3 (which is now out of print), are fairly
with a 107. soln of nitron base in a 5% AcOH rapid and reliable
soln; separate the resulting ppt of nitron Method 1, (Developed during WWII by A.
picrate by filtration, dry it and weigh e) Examine Zabenko at Volunteer Ordnance Works of
the material left after removal of PA, in small Hercules Powder Co, Chattanooga, Term).
portions for other nitrocompds using the same In this method, a sample in which MNT has
procedures as indicated under Qualitative been detected(such as by odor) is treated with
Tests f)Weigh accurately the Iast portion of mixed nitric-sulfuric acid of the strength
material left in the beaker(See opn d) and required to nitrate MNT to DNT and the amt
treat it in cold with 10% Na or K hydroxide soln. of nitric acid consumed is detd by titrating the
This treatment dissolves nitrocompds, leaving excess with standard ferrous sulfate soln
oily and greasy substances(such as castor oil, procedure. Weigh accurately in a 15ml weighing
vaselin, etc) as residue. Wash this residue with bottle a 5g sample and drown the ensemble in
w, dry and weigh g)Examine the non-extractable 100ml of 95% sulfuric acid contained in a
materiaI which was left in Soxhlet(See opn a), 250ml beaker. Add slowly, while stirring by
first by drying and weighing it h)Shake the means of a short thermometer, from a weighing

1
 C 163

pipette about 10gof accurately weighed p C 119-R

“standard” mixed acid keeping the temp in Note 6: The above Method 1 of Zabenko is
beaker below 40~ Cover the beaker with a used for detn of MNT in its mixts with DNT &
watch glass and allow to stand for 15mins. TNT. In order to determine the amt of DNT in
Place the beaker in an ice-salt bath and titrate these mixtures, use Method 2, which follows
the soln with standard ferrous sulfate soln Method 2( Developed During WWII at Keystone
(lml of which corresponds to 0.02g HN03 ) Ordnance Works, Meadville, Pa). Triturate in a
to a permanent faint pink color. Keep the temp medium size mortar a 10. Og sample with ca
in the beaker below 40° 50ml of CC14, allow to settle and decant the
% MNT= [(W1 xC-RXE)X(2.1736 X1OO)] /W, Iiq into a 500ml separator funnel. Repeat this
where WI = wt of std mixed acid; C= % HNO~ in opn 3 or 4 times, transferring each time the
mixed acid; R = mls std FeS04 required, minus Iiq into the same funnel. Shake the contents
0.2ml; E. grams of HN03 equivalent to lml of of funnel for lmin with an equal vol of 17%
std FeS04; and W. wt of sample Na sulfite(f’sellite”) soln (which was previously
Notek Titration as described here does not slightly acidified with H2S04 ) and allow to
give as accurate results as the ‘ ‘back titration” stand until two layers separate. Transfer the
method described under Cellulose Nitrate, bottom layer(soln of DNT in CC14 ) into a
Analytical Procedures, p C 119-R beaker and discard the red, top layer(sellite
Note 2: For prepn of “standard” ferrous with products of decompn of TNT). Transfer
sulfate soln dissolve 176. 5g of FeS04.7H20 the CC14 soln back into the same funnel and
in 400ml distd w contained in a 1000ml vol fl repeat the washings twice with fresh sellite
and add slowly, while stirring, 500ml of cold solns. Then place 2 drops of CC14 soln into the
1: l(by vol) sulfuric acid. After addg distd w to hollow of a porcelain spot plate and add 5
the mark, transfer to a dark reagent bottle for drop~ of freshly prepd coned soln of KOH in
storing. Drop inside the bottle a piece or iron 1:1 alc-acet mixt. If the color developed on
wire(or nail) to prevent the oxidation of ferrous this addn is not purely blue, but has a pinkish
to ferric ion tinge, repeat washing with sellite once more
Note 3: Instead of using the above reagent, and then transfer the CC14 soln to a tared dish.
the ferrous ammonium sulfate soln may be Evaporate the contents on a water bath, under
used. Its prepn and standardization with K the hood(avoiding inhaling the vapors of CC14
nitrate soln are described under Cellulose which are very toxic), cool the dish in a
Nitrate, Analytical Procedures, .p C 119-R desiccator and weigh
Note 4: For prepn of “standard” mixed acid, % DNT= (W1 X 100)/W= W, X 10
add slowly, while stirring, from a weighing where WI = wt of dried residue and W= wt of
pipette, l15ml of 80% CP nitric acid to 2200ml sample(10.Og)
of coned sulfuric acid contained in a large % TNT= 100-% DNT
beaker which is cooled in an ice-salt bath. If DNT content is small(such as below
Transfer the soln to a brown glass-stoppered 10%), while the bulk of material is TNT,
bottle and keep in a cool place another procedure, also described in Ref 3(See
Note 5: For detn of % HN03 in std mixed acid, pp 136-7 ),. might be found more convenient. As
transfer from a weighing pipette 5-8g, accurately ‘ ‘drip oil” used in Cheddites always contains
weighed sample of acid to a 250ml beaker more than 10% of DNT, the other procedure is
contg 100ml of 95% sulfuric acid. Place the not discussed here
beaker in an ice-salt bath and titrate with std DNT may also be detd by titanous
ferrous sulfate soln until a permanent faint chloride buffer method as used by Butts et al
pink coloration for analysis of smokeless proplnts(Ref 3a)
%HN03= [( RxE)x 100] /W1, Chromatographic procedures described
where R = mls std FeS04 required, minus in Refs 2,5 & 6 and IR(infrared) method described
0.2ml; E = grams of HN03 equivalent to lml in Refs 7,8,9,10,12 & 13 can also be used for
of std FeS04; and WI = wt of std mixed acid quantitative detns of nitrocompds in Cheddites
(Ref 3,pp 133-4) (See also Chlorates, Analytical Procedures and
If more accurate results are desired, use under individual chlorates)
the “back titration” method described under Re/s: l)M.Giua, SS 17, 137-9 (1922 )( Chemical
Cellulose Nitrate, Analytical Procedures, analysis of Cheddites) 2)Dr Halfter, SS & NC
 C 164

38, 173-5 (1943 )(Sepn of DNT from TNT by such as K chlorate & perchlorate used as
chromatographic method) 3) Clift & Fedoroff, ingredients of Cheddites) 15 )Dr Omero Vettori
vol 4(1946), 133-4 (Quantitative methods for of’ Societ~ Italiana Esplosivo Cheddite, Torino,
detn of MNT in mixts with DNT & TN~ 134-7 Italy; private communications 1962)
(Qualitative and quantitative methods for detn
of DNT in mixts with TNT) 3a) P. G. Butts et Cheddite-Type Explosives Containing Azobenzene.
al, AnalChem 20, 947-8( 1948)(Detn of DNT See p A647-L in Vol 1 of this Encyclopedia
in proplnts) 4)W. B. Meldrum et al, AnalChem
20, 949-50( 1948)(Detn of K chlorate in proplnts) Cheddite.Type Explosives Used in Finland.
5)T.C. J. Ovenston, JSCI 68, 58(1949 )(Detn of See LHuhtanen, Explosivst 1960, 189-94
expls, including 1-MNN; 1,3-DNB; 2,4-DNT;
1,3,5 -TNB; 2,4,6-TNT; 2,4-DNPh & 2,4,6-TNph Cheesa Sticks. Long pieces of Cordite, coated
by chromatographic methods) 6) Chi-Shau Ling, with Amm oxalate & shellac, which were used>
JChineseChemSoc 18, 135-6(195 I)(in EngI) & instead of fuses, squibs, etc, in British South
CA 46, 2965(1952) [ Sepn of 2 ,4-DNT from other Africa for igniting blasting expls. They were
nitrated products of toluene by chromatographic also authorized for use in England
method. For this a soln of crude nitrated toluene Refs: i) Marshall 2(1917), 540 2) Marshall,
(50g) in 500ml acetone is poured thru a 5.2cm Dict(1920), 21 3)Thorpe 2(1938), 525
column consisting of 80g pure magnesia, at
the rate of 1 drop per sec and then the column Chelation and Chelatometry. Chelatio~derived
is dried. TNT, being strongIy absorbed, pro- from the Gr word “keIos” which means “claw”)
duces a violet zone at the top of the column; is a chemical reaction in which some polyvalent
DNT, being poorly absorbed, forms a green metallic ions(such as Cu++) react with organic
zone at the bottom; and MNT and other products compds(’’chelating agents”) which contain
pass thru the column unabsorbed. DNT may be functional groups(such as -OH, -NH2 or -COOH)
removed from lower zone by extraction with 95% to form extremely stable, water soluble complexes,
ethanol followed by evapn & crystn. The same called chelates. The polyvalent metal in solns
procedure may be used for extraction of TNT of chelates is chemically unreactive and cannot
from upper section of column] 7) F. Pristera, be detected. by ordinary them tests. The term
Applied Spectroscopy 7, NO 3, 115-21(1953) & “chelation “ is sometimes also used to include
CA 48, 1683( 1954) (Infrared method for detg ‘ ‘hydrogen bonding”
TNT & 2 ,4-DNT in admixts such as found in A typical example of “chelation” is
exudates) 8) F. Pristera & M. Halik, PATR formation of “Versene Copper Chelate”, from
2013(1954); AnalChem 27, 217-22(1955) & CA Versene(one of the Dow chelating agents) and
49, 8744( 1955 )(IR method for detg 0-, m-, & the copper ion:
p-MNT’s and 2,4- & 2,6-DNT’s in mixtures)
9) F. Pristera, PATR 2254(1956) [Analysis of NaOOC.H2C CH2.COOH
expls by IR method; 68 spectrograms are giveq “N-CH2-CH2-N ‘ +Cu++ -.,
amorw them are a-MNN; 1,5- & 1,8-DNN’s; NaOOC.H2C” “ CH2 .COOH
MNB; m- & p-DNB’s; 1,3,5 -TNB; p-MNPh;
2,4-DNPh; 2,4,6-TNPh; o-, m- & p-MNT’s; NaOOC.H2C\ . CH2 .H2C1 ~,CH2 .COONa
2,4- & 2,6-DNT’s; a(2,4,6)-, ~(2,3,4)- & ‘N.
y(2,4,5)-TNT’s; AN & Amm picrare] 10)W.E. ,/ ‘CU ‘- ?.cH
Fredericks & F. Pristera, PATR’s 2485( 1958) & H 2,C’ \
2
2546( 1958)(IR merhod for detg MNT’s, DNT’s & o= c-o “ o-&o
TNT’s in admixts) 1 l)Giua, Trattato, 6( 1959), In chelated Versene, the copper ion has
470-71 12)W.E.Fredericks & F. Pristera, PB become a member of an inner ring structure in
Report 137467 & CA 54, 12585( 1960) (Same info the molecule and is inactivated. It will remain
as in PATR 2546 of Ref 10) 13) F. Pristera et so unless it is desired to reverse the process,
al, AnalChem 32, 495-508(1960) & CA 54, such as in polymerization of synthetic rubber
1285 -86(1960 )( Analysis of expls by IR Chelates find numerous applications in
spectroscopy) 14) Anon, “Analysis for Powders chemical industries and in some analytical
and Explosives”, AB Bofors Nobelkrut, Bofors,
procedures, including those used in explosives
Sweden(1960), 148-50 (Analysis of substances, Iabs(see CA’s under Chelatometry)
 C 165

An example of application of chelatomet- Chemecol is considered as one of the

ry to analysis of expls is given under Ref6 safest and efficient devices for breaking coal
Re/s: l)H.Diel, ChemRevs 21, 39-111(1937) and it can be used” in most dangerous gaseous
(the chelate rings) 2)Kirk & Othmer 4(1949), and/or dusty coal mines (Refs 1,2,3 & 4)
382(under Coordination Compounds) 3)Karrer Other devices, similar to Chemecol are:
(1950), 520 4)A.E.Martell & M. Calvin, Airdox - operated by compressed air, mentioned
“Chemistry of the Metal Chelate Compounds”, in Vol 1, of Encyclopedia, p A 117-R and
Prentice-Hall, NY( 1952) 5) Anon, C & EN described in Ref 4,pp 137-42.
1956(Feb 27), 956-7( The chemistry of chelation) Armstrong - operated by compressed air,
6)J.VIe3tAl et al, ChemPr&mysl 6, 50-2(1956) & mentioned in Vol 1 of Encyclopedia, p A485-L
CA 50, 14229( 1956) (Chelatometric method and described in Ref 4,pp 137 & 140-42
suitable for detn of lead in expls, such as Cardox - operated by gas produced on heating
Pb picramate, -styphnate, -azide or -picrate liquid carbon dioxide, briefly described in Vol
is described) 7) CondChemDict(1961), 24&9 2 of this Encyclopedia and more completely in
8)S.Patai, “Glossary of Organic Chemistry”, Ref 4,pp 123-7 and
Interscience, NY(1962), 39 Hydrox - operated by gas produced on heating
a mixt of Na nitrate & Amm chloride(See Ref 4,
Chemecol (Spelled <‘Chemocol” in Ref 1). It pp 127-33)
is a chemico-mechanical device(developed by Re/s: l) Anon, “DuPont Invention Points to
Du Pent Co) which breaks coal from the mine New Era in Coal-Mining”, C & EN 29, 1745
face by the force of compressed gas which is (1951) 2)Blasters’Hbd( 1952)., 79-82 3)Cook
generated by chemical reaction within the (1958), 16 4)Taylor & Gay(1958), 133 and
device and is released mechanically. Chemecol plate 9 facing p 160
assembly consists of a long, narrow, steel
tube, closed at one end by a plug equipped with Chemical Aerial Bombs. See under Chemical
electrical connections, and, at the other end, Bombs
by a rupture disc held in place by a discharge
head. Inside this tube is a gas generating unit CHEMICAL AGENTS or CHEMICAL
composed of a c<starter mix” and a “pressure WARFARE AGENTS(CWA)
mix’ ‘(usually a non-detonating AN-fuel mix). A (Agents chimiques or Gaz de combat in Fr;
metallic, conductive, starter ribbon is imbedded Chemische Kampstoffe, Kampfstoffe or
in the starter mix and this ribbon is connected Gaskampfstoffe in Ger; Aggressive, Aggressive
electrically to the plug and then(thru a cable) chimice or Gas di guerra in Ital; Agresivos
to a 36 volt storage battery. Usually several qu~micos or Gas de guerra in Span; Otravliayu-
Chemecol tubes are placed in a borehole shchiye Veshchestva(OV), Boyevyiye OV~
drilled in the coal face and the tubes may be Boyevyiye Gazy or Boyevyiye Khimicheskiye
discharged either one at a time, or multiple Veshchestva in Rus). CWA’S are chemical
connections may be made to discharge several items(except explosive and pyrotechnic compns)
tubes at a time. In order to start the gas used for military purposes, both offensive and
generating reaction, it is sufficient to pass defensive. The most important of these items
a current of ca 8amps thru the ribbon for 6 to are substances known as “war gases” or
10secs. Once started, the reaction continues “poison gases”. These are used to produce
to liberate gas until a predetermined pressure, lethal, injurious or irritant effects resulting
such 15-20 thousand psi, is reached. Then, in casualties
the disc is ruptured and the gas rushes out Under the term of ‘<chemical agents” are
thru the ports in the discharge tube and breaks also understood items used for starting fires
the coal, without danger of igniting the mine in enemy installations, houses~ .ships~ or
gas or coal dust. Prior to rupture of disc, vehicles(see under INCENDIARY WARFARE)
breakage or disintegration of starter ribbon as well as substances producing smokes
takes place and this interrupts the circuit of serving for screening movements of troops,
battery, thus eliminating the possibility of ships, trains, or vehicle s(See under SMOKES
formation of an elec spark which might ignite IN WARFARE)
coal gas released at the time of breaking of the Smokes producing compns used for
disc signaling purposes(such as colored smokes)
 C 166

are usually classified as pyrotechnic items the most effective one of the entire WWI, because
Historical. The use of poisonous materials for it met the Allied Armies both unprep~ed and
military purposes was known in Biblical times. unprotected. May casualties were caused by
These poisons were obtained from plants or this attack(Ref 16,pp 21-2 & 42). In early
snakes, and poisoning of food, wine or water subsequent attacks, the asphyxiating gases,
produced many casualties among enemy troops. such as compressed chlorine or phosgene,
Poisons were also used to smear tips of were released from containers(in which they
arrows and, when firearms came into use, some were kept under pressure) at a time when the
poisonous bullets were made. It does not seem wind was blowing towards the enemy lines.
that such bullets are used now but poisonous This was known as “gas-cloud method”. Later
arrows are still used by some natives in this procedure was replaced by the use of
Africa, Asia and Australia c‘chemical shells” which were filled with
Use of smokes, fumes or gases to produce chemical agents. On bursting of these shells,
casualties is also a very old practice. Smoke the chemicals were scattered in the air
and fumes produced on slow-burning of green inflicting damage where required. The Allies
wood(w or w/o resins, pitch, sulfur or arsenic) immediately followed the Ger example and
was used by some ancients to drive out men soon surpassed the Ger efforts. This type of
and animals from caves or other dwellings(Ref warfare was widely used thruout .WWI
16,p 13-20). The earliest recorded attack, Although “chemical warfare” was outlawed
which may be considered ,as “chemical gas” after WWI by the Hague Convention, all great
took place during thePeloponesianWar(431 to nations were prepd before and during WWII to
404BC) when Spartans directed the fumes resort to this kind of war again, and many new
produced on burning green wood(mixed with tar, “chemical agents” were developed. The most
sulfur and arsenic) towards the besieged prolific in this respect were the Germans, who
Athenians in towns of Plataea and Delium developed, among other compds the so-called
(Ref 16,p 20 & Ref 59,p 420). Another example “nerve gases “(Refs 35 & 52). None of the
of chemical attack took place in 187BC when nations ventured, however, to use during WWII
the people of Ambrajia drove out the Remans any asphyxiating gas, although smokes and,
(who besieged their town) by means of fumes especially, incendiaries were used to a great
produced from barrels filled with feathers and extent
glowing coals (Ref16,p 20). Poisonous fumes US chemical agents are subdivided, accdg
produced on burning of green wood(w or w/o to the ‘ ‘Ordnance Corps Manual” ORD M 7-224
other substances) were used in many was (Ref 36), into three groups: Group A consists
including the Franco-Algierean Wat when Gen of “blister’’ gases, such as H, HD, HN, and L.
P.$lissier succeeded in suffocating a great They are the most dangerous to handle and
number of natives(Kabyls) by burning large require for protection not only a gas mask but
quantity of green wood and directing the fumes special clothing, including heavy rubber boots
against the narives. This took place in 1845 and heavy rubber gloves; Group B consists of
(Ref 16,p 21) nonpersistent(choking, blood & nerve-, tear-
More effective chemical agents were proposed and vomiting-) gases, (such as CG, PS, AC, CK,
during Crimean War( 1853-56) and during Amer DA, DM, CL, CNS and CNB) and smokes(such
Civil War(1861-65 ). These included sulfur as FM and FS). They require for protection gas
dioxide, suggested by Brit Gen Dundonald, for masks and gloves. Personnel handling liquid
use against the Russians besieged in Sevastopol acid-type them agents should wear also
(Ref 16,p 21) and Amer proposals to use rubber boots and aprons; Group C includes
chlorine, cacodyl, cacodyl oxide or an irritating WP and PWP and should be handled by
gas produced on heating a mixt of sulfuric and personnal equipped with flame-proof gloves &
hydrochloric acid(Ref 53). None of these coveralls, and chemical safety goggles
materials, however, was applied in practice The majority of agents prepd or investigated
Modern chemical warfare began with the in US have been assigned “symbols” or other
German gas attack at Ypres, France on April names which have no relationship to rheir
22, 1915, when 5700 cylinders filled with them compns. These agents are listed below
chlorine gas, were blown against French and in alphabetical order of their code letter. No
Canadian trenches, This first gas attack was classified information is included here
 C 167

AC. Hydrogen Cyanide or Prussic Acid(Fr DC, Diphenylcyanoarsine(Ger Clark II),

Vincennite or Manganite), HCN; CO1 liq with (C6H5)2ASCN; soIid; dispersed by heat; it
odor of bitter almonds, bp ca 78°F(25 .60.); produces an a~rosol, irritating respiratory
lethal when inhaled; one of the “blood” gases passages and causing nausea and headache.
(Group B,nonpersistant them agents )(Ref 16,p It is one of the “vomiting” gases(Ref 16,pp
242 & Ref 36,P 29-27) 199-201 & Ref 54a,p 68)
BA. Bromoacetone(Fr Martonite, Ger B-stoff), DM Adamsite or Diphenylaminechloroarsine,
Br.CH2.C0.CHa; CO1 liq, bp 136.5°; violent HN(C5H4)2ASC1; grn-yel to blk solid, mp
irritant, mainIy for the eyes; was used during 383 °F(ca 1950); dispersed by heat to produce
WWl(Ref 16,pp 142 & 172) an aerosol causing skin and eye irritation,
BBC or CA. a-Bromobenzylcy anide(Fr Carnite), headache and nausea(Ref 16,p 206; Ref 25a,p
C6H5.CH(CN)Br; yel trysts melting at 17° F 172; Ref 36,p 29-29). It is one of the “vomiting”
(25°) to a brownish oil, which boils at gases(Ref 54a,p 67)(See also Vol l,p A491-R
437°F(ca 225°) giving a heavy vapor of soured under Arsine Derivatives, Organic)
fruit odor; it is one of the tear gases(Ref 16, DP. Diphosgene or Trichloromethylchloroformate
pp 181 & 292; Ref 25a, P 172) (Fr .%rpalite; Ger Perstoff), CI.CO0.CC13;
CDA Accdg to Bebie(Ref 22,p 63) it is CW oily liq with musty hay odor, bp 260.@ F
symbol for DiphenybanOarsine~ see DA (ca 127°~ acts as lung irritant similarly to
CG. Phosgene or CarbonyI Chloride(Fr CG(Ref 16,pp 154-5 & Ref 25a,p 170)
Collongite, Ger D-Stoffe), COC12; COI liq with ED. Ethyldichloroarsine(Ger Dick or Griinkreuz
odor of fresh cut hay, bp 47’0F(8.3°); when -3), C2H5 .AsC12; oily liq with biting pepper
inhaled causes pulmonary endema(Group B, -like odor; bp 312 °F(ca 1560); acts as lung
nonpersistent)(Ref 16,p 154; Ref 2$a,p 170 & irritant(Ref 16,pp 143 & 195-6; Ref 25a,p 168)
Ref 36,P 29-24) (See also Vol l,p A491-R, under Arsine
CK. Cyanogen Chloride(Fr Vitrite or Mattguinite] Derivatives, Organic)
CNC1; CO1 Iiq with pungent odor, bp 55°F FM. Titanium Tetrachloride(Ger F-Stoff),
(12.80); lethaI when inhaled(Group B, non TiC14; heavy, CO1 liq which solidifies at
persistent)(Ref 16,p 248 & Ref 36,p 29-28) -9°F(ca -230);, bp 277°F; produces in moist
CL. Chlorine(Fr Bertholite, Ger Chlor), Clz; air dense white clouds with acrid odor(Ref 16,
grn-yel’ gas with pungent odor, bp -30° F(-34.40); p 269; Ref 25a,p 174; Ref 36,p 29-31 & Ref
lung irritant often lethal(Group B, nonpersistent) 54a,p 69)
(Ref 16,p 151; Ref 25a,p 171 & Ref 36,p 29-30) FS. Sulfur Trioxide in Chlorosulfonic Acid
(See also Chlorine) (55/45), SOa-SO~HCl; heavy liq with pungent
CN. Chloroacetophenone or Phenacyl Chloride, odor; fr p -22° F(-30°); fumes strongly in air
CSH5 .CO.CH Cl; greyish solid with fruity producing dense white smoke(Ref 16,p 268;
odor, mp 129 8 F(54°); it is a strong tear-producing Ref 25a,p 174; Ref 36,p 29-32 and Ref 54a,
substance(Ref 16,p 176 & Ref 36,P 29-29 p 68)
CNB. Soln of CN in mixt of benzene and GA. Ethylphosphorodimethy lamidycyanadate
CC14; fr p 19°F(-7Q20); acts as tear gas(Ref or Monoethylester of dimethylaminocy ano-
36,p 29-31 & Ref 54a,p 67) phosphoric acid(Tabun, Trilon 83, T83 or
CNC. Soln of CN in chloroform; acts as tear TIOO in Ger), o
gas(Ref 54a,p 67)
CzH5.0.# .N(CH3 )2 ;
CNS. Soln of CN in mixt of PS(chloropicrin)
& Chloroform; fr p 35 °F(l.70); acts as teat gas CN
(Ref 36,p 29-30& Ref 54a,p 67) COI to dk-brn oil; was first prepd before WWII
DA. DiphenylchIoroarsine(Ger Clark I), in Germany and Switzerland and planned to be
(C6H5)2ASC1; a viscous semi-solid mass used in Chem bombs and rockets(Ref 52,p Ger
varying in color betw wh & blk; mp 111°F(ca 204 & Ref 55)
440)- 9 gives on heating an aerosoI causing skin GB. Isopropylmethylphosphonofluoridate or
& eye irritation, chest distress and nausea Isopropylester of methylfluoropho spheric acid
(Ref 16,pp 143 & 196; Ref 36,P 28-29). It is (Sarin, Tril~n 46. T46 or T114 in Ger),
one of the vomiting gases(Ref 54a,p 67)(See
also Ref 22,p 6~). This compd is designated in (H~C)zCH.$P.CH~; COI & odorless, very
Ref 25a,p 173 as PD(qv) F
 C 168

volatile liq, about 3 times as toxic as GA; CN-2 and CN-3 in Ref 52a,p 68, but their
quick-acting agent of medium persistency; was compn is not given. It is mentioned however,
first prepd before WWII in Germany and that they produce more permanent damage than
Switzerland(Ref 52,p Ger 204; Ref 54a,p 68 H or HD. Since WWII, these compds have been
& Ref 55) studied in US and GtBritian
GD. P inacolylmethylphosphonof luoridate or HT. Symbol for CWA called ‘ ‘Mustard Gas
Pinacolicester of methylfluorophosphoric Agent T’‘(Ref 54a,p 152)
acid(Somon in Ger), o KT (Brit). Tin Tetrachloride(Fr Opacite),
(CH3 )3 C. CH.0.#.CH3 ; SnC14; CO1 liq, bp 136.4°; produces wh smoke
which is not corrosive; was used during WWI
~H3 i
CO1, camphor-smelling Iiq; less volatile but in mixt with CG & PS in some shells(Ref 16,p
more toxic than GB; was first prepd before 269)
WWI1 in Germany and Switzerland(Ref 52,p L. Lewisite or Chlorovinyldichloroarsine(Ml),
C1.CH:CH.~sC12; dk-grn oily Iiq with odor
Ger 204 & Ref 55)
resembling that of geraniums; fr p 15°F(ca
GF. Cyclohexylmethylphosphonofluoridate or
CyclohexyIicester of methyIfIuorophosphoric -9.40); it boils ca 374°F(1900) yielding a dense
acid, vapor, acting physiologically similarly to H;
$
in addn, it is a systemic poison when absorbed
C~CH.0.~.CH3 (Ref 55) into the body thru the skin or lungs. It is less
F persistent than H(Class A of them agents)(Ref
H (or HS). Mustard Gas, ThiodigIycoI Chloride 16, 202-6; Ref 25a,p 167; Ref 36,p 29-12 and
or DichIoroethyI Sulfide(Fr Yperite; Ger Lost Ref 54a,p 68) (See also Vol l,p A491-R, under
or Gelbkreuz), S(CHZ .CH2 .C1)2, brn oily liq Arsine Derivatives, Organic).
with horseradish or garlic odor, fr p ca MD. Methyldichloroarsine( Ger Methyldick),
50°F(100); causes bIistering(vesicant) effect CH3.AsC12; blister gas(Ref 16,p 143; Ref
on the skin. It is a persistent them agent 22,p 101). Compate with ED and PD
belonging to Class A, which is the most PD. Phenyldichloroars ine(Fr Sternite),
dangerous to handle(Ref 16,pp 221-39; Ref 25a,p C6H5 .AsC12 . A liq which can be dispersed by
166; Ref 36,p 29-10 and Ref 54a,p 68) expl action or as a spray to form a delayed
HC. Mixture of hexachloroethane, C13 C. CC13Y action casualty gas of low persistency. Classed
with Zn dust, NH4C104 & NH4 Cl; produces as “blister” gas, it also acts as vomiting gas
on burning a grayish-white smoke which serves (Ref 54a,p 68)
for screening(Ref 16,p 270 and Ref 25a,p 174) In Ref 25a,p 173, PD is Iisted as
HD. Distilled Mustard(puified H); amber Diphenylchloroarsine(Compare with DA)
-colored oil, fr p 58 °F(14.50); bp 433.6°F PS. Chloropicrin, Nitrochloroform or
(223°) with decompn; practically odorless and Trichloronitromethane( Brit Vomiting Gas; Fr
much more difficult to detect than impure Aquinite; Ger Klop), C13C.N02; CO1 liq with an
product.; produces, the same effect as H(Ref odor resembling that of anise, bp 231.5-234°F
25a,p 166; Ref 36,p 29-10 & Ref 54a,p 68) (ca 1470); class B them agent, intermediate
HN. Nitrogen Mustards are defined by Sartori in toxicity betw CL & CG(Ref 16,pp 1s8-61;
(Ref 35,p 226) as tertiarY 2 ,2’-dihalodialkyl- Ref 25a,p 169; Ref 36,p 29-26 and Ref 54a,p
amines, more particularly 2 ,2’-dichlorodiethyl- 69)
amines of the structure, R-N(CH2CF$ Cl)z, PWP. Plasticized White Phosphorus. A finely
in which R is an alkyl, haloalkyl or aryl group. divided WP suspended in gel of rubber and
The name’ “nitrogen mustards” is derived from xylene. It is a smoke producing agent with
the structure similarity to mustard gas(see H), side incendiary effects. Its action is similar
They are also called ‘%adiomimetric poisons” ro WP except that it is slower burning(Ref
because many of their biological props are 36,P 29-41 & Ref 54a,p 68). Both PWP and WP
like those of ionizing radiations. Their toxic are Class C chemical agents
props are similar to those of H or HD. They Q. A chemical agent of specialized application
were first prepd in Germany before WWH. A (Ref 54a,p 68)( Its formula is secret)
table lisring 22 “nitrogen mustards” is given T, A chemicaI agent of specialized application
on p 228 of Ref 35. One of these CN-1 is (Ref 54a,p 68)(Its formula is secret)
listed in Ref 36,p 29-11 and three: CN-1, TH 1. Thermite. An incediary chemical agent
 C 169

composed of an intimate mixt of ca 73% FeO C1CH2.C0.C2H5 was used by the French, as
& 27% of finely granulated Al; used in items a tear gas, under the name of Homomartonite
of ammo to provide a source of heat to cause (Ref 16,pp 175-6) m)Dibromoethylsulfide(Fr
fires at target(Ref 16,p 263; Ref 25a,p 176 and Bromlost),(Br2CH2 .CH2)2S(blister gas)(Ref
Ref 54a,p 68) 16,p 292). Compare with Mustard Gas(CW
TH2. Thermate. An incendiary chemical agent symbol H or HS) n)Ethyliodoacetate( B.rit SK),
composed of an intimate mixt of TH1 with a C2H5.00C.CH21(tear gas)(Ref 16,pp 164-5)
binder and an addnl oxidizer. It was formerly o)Dichlorodimethylether, C1H2C.0.CH2C1
used as an igniter for magnesium bombs(Ref (acts like CG)(Ref 16,pp 166-7) p)Di-
54a,p 68) bromodimethylether, BrH2C.0.CH2 Br(acts like
VX. Persistent them agent. Its formula is CG)(Ref 16,pp 167-8) q) Bromoxylene,
secret, but its uses are discussed in CH3 CH2 Br
unclassified ~CAssembly of Explosive Components”, C6H4< and Dibromoxylene, C6 H<
Technical Bulletin TB 9~1300s2031 (1961) CH2 Br CH2 Br
WP. White(Yellow) Phosphorus. A It yel waxy (tear gases)(Ref 16,pp 182-3) r)perchloro-
solid,mp llO°F(ca 430), bp 549°F(ca 2870). methylmercaptan, C13C.SCl(irritant) (Ref 16,pp
It is chemically very active and upon contact 213-14) s) Thiophosgene(Fr Lacrimite),
with air burns with a luminous flame producing SiCC12(tear gas)(Ref 16,p 214) t)Methyl-
dense white smoke which is not toxic, unless cyanoformate, CH3.0.C0.CN and Ethyl-
it is very dense. When loaded in ammo, it is cyanoformate, C2H5.0.C0.CN. A mixt of
dispersed by a burster chge. It is very toxic these products with the addn of ca 10% of the
if taken internally(Ref 16,p 262; Ref 25a,p esters of chloroformic acid was used by the
1?5; Ref 36,P 29-41 and Ref 54a,p 69) Ger Army during WWI under the name of
In addn to the above US chemical agents <‘Cyclon’‘(Ref 16,pp 251-3) u)Daisite,Fr
(some of them probably obsolete), the following thermite mixts(Ref 16,p 265) v)Brit “S”
compds, which were developed during and Mixture produc~d brn-yel smoke of low
after WWI, may be mentioned: a)Ethylchlorosulfo- screening power(Ref 16,p 268) w)Brit ‘tKT”
nate(Fr Villantite), C2H5 .S02 OCl(lung (Fr Opacite), SnC14 - was used in some Fr
injurant)(Ref 16,pp 142 & 208) b)Chloromethyl- smoke shells in mixt with phosgene(see CG)
chloroformate, (C1.CH2 ). COOC1 in mixt with and chloropicrin(see PS)(Ref 16,P 269)
Dichloromethylchloroformate, {Clz .CH).COOC1 Several hundred new chemical agents
was used. as lung irritant) called in German were developed and tried in Germany before
*’K.Stoff” or ‘tC-Stoff’’(Fr Palite)(Ref 16,pp and during WWII(Ref 52,p Ger 28), the most
161-3 ). This mixt replaced Methylchloro- important of them was a group of Trilons,
sulfonate, C1.S02.0CH3(Ref 16,p 211) c) which included Tabun, Sarin(c’nerve gas”)
Dimethylsulfate(Fr Rationite; Ger D-Stoff), and Somon(Ref 52,p Ger 204). Tabun and
(CH3 )2 S04(blister gas)(Ref 16,pp 214-20) d) Sarin are also described in Ref 35,pp 253-4
Phenylcarbylaminechloride(Ger ‘!K2-Stoff’ ‘), Sartori(Ref 35) described under the title
C6H5.NCC12(lung injurant)(Ref 16,pp 253-5) of ‘tNew Chemical Warfare Agents”, the
e)Phenyldibromoarsine( Ger X-Stoff), C6H5.- following compds: Nitrogen Mustards(Ref 35,PP
AsBr2(lung injurant)(Ref 16,pp 201-2) f) 226 & 228)( See also under CW symbol HN);
Cyanogenbromide( Brit CB; Austrian CE; Ital Fluroacetates, which comprise the esters of
Campiellite), CNBr(systemic poisoning)(Ref fluoroacetic acid and of higher co-fluorocarbo-
16,pp 250-1) g) Benzylbromide(Fr Cyclite; Ger xylic acids of the general formula F(CH2 )n-
T-Stoff), C6H5.CH2 Br(irritant or tear gas)(Ref COOR. The first compd of this series, methyl-
16,pp 178-80) h) Benzyliodide(Fr Fraissite), fluoroacerate, FCH2COOCH~, was prepd in
C6H5.CH21(same as bromide)(Ref 16,p 180) 1896 by Swarts but possibility of its use as
i)Chloroacetone(Fr Tonite; Ger A-Stoff), CWA was not discovered until shortly before
CH3 .C0.CH2Cl(irritant or tear gas)(Ref 16,pp WWII. Many other fluoroacetates were prepd
142 & 171-2) j) Bromoacetone. See CW symbol and investigated before and during WWII. It
BA k)Martonite, Fr them agent consisting of was planned to use some of them as water
bromoacetone 80 & chloroacetone 20%(Ref contaminants(Ref 35,pp 236-7). In tables 3,4,
16,p 176) l) Bromomethylethy lketone, BrCH2.- 5,6 & 7 of Ref 35 are listed various
C0.C2H5. Its mixt with Chloromethylethy lketone, fluoroacetates. As a rule, they are highly
 C 170

toxic when inhaled and to a lesser extent when (Chem identification of war gases) 22)Bebie
absorbed thru the skin; Fluoropbospbates are (1943), 29,38,44-5,47-8,53-4,56-7,62-5,70,79,
comprised of the diesters of fluorophosphoric 87,100-1,147-8, & 160-2 23)R.Agrelo & J.M.
RO>P:F Franci, AnalesAsocQuimArgentina 31, 30B
acid the substituted diamidophos-
RO ’0’ (1943) & CA 38, 2763( 1944)(History &
R2N F classification of war gases) 24) A. Izzo.,
phoryl fluorides ~ ~)P;m and related
“Guerra Chimica e Protezione Antigas”,
2 Ro, ,F Hoepli, Milano( 1944) 25)A.H.Waitt, “Gas
substances, such as R Nz~, of
2 Warfare”, Published by Infantry Journal,
RO ,F
JP~ , where R is an alkyl, aryl or Washington,DC( 1944) 25 a)Anon, “Ammunition
RO Inspection Guide”, TM 9D190A(1944), 26)G.J.B.
cycloalkyl group(Ref 35 ,pp 245-6). In tables Fischer, “Incendiary Warfare”, McGraw-Hill,
8,9 & 10 of Ref 35, are listed several of these NY(1946) 27)US Strategic Bombing Survey,
compds “Powder, Explosives, Special Rockets, .Jet
R e/s: l) Pascal( 1930), 247-302(Gaz de combat) propellants, War Gases and Smoke Acid”,
2)Ullmann 6( 1930)( Kampfstoffe, Chemische),pp Ministerial Rept No 1, Exhibits CD and CH,
419-33(not found in new edition) 3 )Anon, Oil Division, Washington,DC( 1947) 28)Z.M.
‘{A Handbook of Chemical Warfare Agents”, Bacq, ActualitdsBiochim 8, 1-48( 1947) (Recent
US GovtPtgOff, Washington,DC(1931 ) 4)A. work on toxic war gases; a review with 60
Izzo, “Guerra Chimica e Difesa Antigas”, refs) 29)USArmy ChemicalCorps, ~’The
Hoepli, Milano( 1933) .5)M.Sartori, “Die Chemical Warfare Service in World War II”,
Chemie derKampfstoffe ~~,Vieweg, Braunschweig Reinhold, NY(1948) 30)W.A.Noyes, “Science
(1935) 6)R.Hanslian, “Der chemische Krieg”, in World War II”, Little, Brown & Co, Boston
](Milit5rischer Teil), Verlag von Mittler, ( 1948), 141-260(Chemical warfare agents);
Berlin(1936) 7)A.M.Prentiss, “Che~i.cals in 274-91 (Screening smokes); 292-5 (Toxic aerosols);
War; A Treatise on Chemical Warfare”, 3 18-32(Offensive them warfare; 388-409( Incendiary
McGraw-Hill, NY( 1937) 8) J. Meyer, ‘“Der bombs); 410-19 (Incendiary fuels); 420-30 (Flame
Gaskampf und die Chemischen Kampfstoffe”, -thrower development) 3 I)R.T.Williams “The
Hirzel, Leipzig( 1938) 9)M.Sartori, “Chimica Biochemical Reactions of Chemical Warfare
delle Sostanze Aggressive” , Hoepli, Milano Agents:’ UnivChicagoPress, Chicago(1948)
(1938) and its Engl translation:. !<The War 32) J. MacRae, AFCJ(Armed Forces Chemical
Gases. Chemistry and Analysis”, Churchill, Journal) 3, No 7, 30-3(1950) & CA 443179
London( 1939), 10)W.Kinttof, “Experiments ( 1950)(Chem warfare; a review of research
in Warfare Chemistry”, Massie PubgCo, progress during 1931 to 1949 incl) 33)A.C.
London( 1939) 1 l)Thorpe 3( 1939), 7-22(Chem Auliffe, AFCJ 3, No 8, 28-9(1950) & CA ~,
warfare) 12)H.F.Thuillier, “Gas in the Next 5037( 1950)(Industry and Chemical Corps)
War”, Goefrey Bles, London( 1939) 13 Anon, 33a)G.L junggren, “Stridgaser och Gasskyd”,
“The Detection and Identification of War Gas”, Zivilverteidigungsverbandes, Stockholm( 1950)
ChemPubgCo, NY( 1939) 14)A.Meyer”, Les 34)Kirk & Othmer 7(195 1), 117-45(Gas warfare
Gaz de Combat”, Ch. Lavauzelle, Paris( 1940) agents) 35)M.Sartori, ChemRevs 48, 225-57
15 )W.Schweisheimer, MedRecord 154, 196-8 (1951) & CA 45, 5337( 1951)( New developments
(1941) & CA 36, 185(1942 )(Historical discussion in the chemistry of war gases; a review with
on uses of poison gases, poisonous arrows and 120refs) 36)Anon, “’Ordnance Safety Manuai
venomous snakes in war) 16)C. Wachtel, ORDM 7.224( 1951),pp 29-11 to 29-5 l(Classifica-
“Chemical Warfare”, ChemPubgCo, Brooklyn, tion of chemical agents as A,B & C; packing,
NY( 1941) 17)M. B. Jacobs, ‘War Gases, Their marking, handling, storage, fire hazard, shipping,
Identification and Decontamination”, Inter- first aid treatment and destruction) 37)Anon,
science, NY( 1942) 18) F. A. Hessel., M. S. Hessel & “Field Behavior of Chemical Agents”, TM
J. W.Martin, t Ichemi Stw in Warfare”, Hastings Y240(1951) 38)E.F.Bullene, AFCJ 5, No 4,
House, NY(1942) 19)A.H.Waitt, “Gas Warfare”, 4-7(1952 )( Effectiveness of them warfare)
Duell, Sloane & Pearce, NY(1942) 20~.D. 38a) A. M. Prentiss, Jr, AFCJ 5, No 3, 2-4
Leake & D. F.Marsh, JChemEduc 20, 339-43 (1952) & CA 46, 4699( 1952)(Chem warfare in
(1943 )(Action of war gases) 21)A.F.Claflin & the Air Corps) 39)EncyclBritannica !5(1952),
F.C.Hickey, JChemEduc 20, 35 1-7( 1943) 354-60(Chemical warfare), 39a)G.Castel.
franchi & P. Malatesta, “Lezioni di Chimica t ‘Employment of Toxic Chemical Agents”, TM
di Guerra”, Ed Studium, Roma( 1954) 40) 3~200A( 1961 )(Conf)(Not used as a source of
Anon, “Chemical Filling and Handling info) 59)Dr 0. Eisenschiml, Chemist 39,
Equipment”, TM 3-255(1955) 41)A.Kondritzer, 421(Dec 1962) 60)US Military Specifications:
US Armed Forces MedJ 7, 791-6(1956) & CA MIL-C-357A, MIL-C-379A, MIL-C-10338B,
50, 10308( 1956) (Chemistry, detection and MIL-C-10463B, MIL-C-10758C, MIL-C-5 1029 and
decontamination of nerve gases) 42)Anon, others
“Military Chemistry and Chemical Agents”,
TM 3*2 15(1956) 43)Anon, “Medical Manual of Chemical Ammunition. Ammunition in which the
Chemical Warfare”, BritCrownCopyright, filler has the basic function of producing a
ChemPubgCo, NY(1956) 44) Anon, “Ground toxic or irritant effect on the body, a screening
Chemical Munitions”, TM 3*300( l$?56) 45) effect(smoke) or an incendiary action(See also
G. Schenk, “The Book of Poisons”, Swets & Chemical Energy Ammunition, Chemical Bombs,
Zeitlinger, Amsterdam( 1956)(Section on them Chemical Grenades, Chemical Gun. Howitzer
warfare agents) 46) A. Koblin & J. Epstein, and Recoilles Rifle Shells, Chemical Land
AFCJ 11, No 5, 24-7(1957) & CA 51, 18392-3 Mines, Chemical Mortars & Chemical Mortar
(1957 )( Field sampling and analysis of nerve Shells, and Chemical Rockets
gas) 47)B.Gehauf & J. Goldensen, Anal Chem Re/s: l)Ohart(1946), 86,101,105,120,220,234,
29, 276-8(1957) & CA 51, 6434( 1957)( Detection 268,290,355,357-8 & 362 2)Anon, “ordnance
and estimation of nerve gases by fluorescence Safety Manual”, Dept of the Army ORDM
reaction) 48) Anon, “Storage, Shipment and 7s224, C3, Paragraph 209(1954) 3)Anon,
Handling of Chemical Agents and Hazardws “Ground Chemical Munitions”, TM 3.300(1956)
Chemicals”, TM 3-250( 1957) 49)CoHier’s
Encycl 19(1957), 332-38( Warfare, chemical) Chemical Ammunition, Destruction of. See
50)J.Goldensen, AnalChem 29, 877-9(1957) under Chemical Munitions; Destruction, Handling,
& CA 51$ 11940(1957)(Detection of nerve gases Storing and Shipping of
by chemiluminescence) 5 l) Anon, “Capabilities
and Employment of Toxic Chemicals”, TM Chemical Ammunition, Testing of. In testing
3200((1958) 52)PATR 251 O(1958),PP Ger 28 bombs, grenades, or projectiles filled with
& 204(Some Ger them warfare agents developed poisonous gases, the firing and observation
before and during WWII) 53)W.D.Miles, AFCJ personnel must be equipped with gas masks
1.2, No 2, 26-7 & 33( 1959); CA 53, 6 12(1959) and other necessary equipment. Direction of
(Chemical warfare agents proposed, but not wind and its velocity must be taken into con-
accepted for use in Amer Civil War) 53a)W.D. sideration before testing to prevent the liberated
Miles, AFCJ 12, NO 5, 34-6(1959) & CA 53, gases from endangering nearby localities
612( 1959)(Chem weapons used in US ca 1825 Re/: Anon, “Ordnance Safety Manual”, ORDM
included stink balls, fire rain and smoke pots) 7*224, C7(1958)
54)M.Giua & M. Civera, “Aggressivi Chimici”,
pp 501-56 and L. Stefanini, “Fiammiferi’’,pp Chemical Artillery Ammunition. See Chemical
559-609 in Giua’s, “Trattato di Chimica Gun, Howitzer & Recoilless Rifle Shells and
Industrial”, UTET , Torinol VI( 1959) 54a) Chemical Mortar Shells
Glossary of Ord( 1959) 55)D.N..Kramer et al,
USP 2926072( 1960) & CA 54, 13502(1960) Chemical & Bacteriological Warfare. Chemical
(Calorimetric detection by means of oximes, warfare (CW) is defined under Chemical,
such as 4,4’-bis(dimethy lamino)benzophenone Biological and Radiological(CBR) Warfare.
oxime, of chemical warfare “G” Agents: GA,GB, Bacteriological warfare, which may be
GD & GF) 56)R.W.Pfeil, USP 2921791(1960) considered as a branch of biological warfare, is
& CA 54, 14510( 1960)( Calorimetric detection conducted with ammunition(such as bombs)
of above G agents by means of a crayon con- filled with deadly or sickness-producing
sisting of di-Na diisonitrwoacetone hexahydrate bacteria
20, o-toluidine. 20, urea 15,, Li stearate 27, Re/: Glossary of 0rd(1959), 28
LiCl 3 & CaO 15%) 57)G,H..Gray, “Laboratory
Handbook of Toxic Agents”, Prentice-Hall, Chemical, Biological and Radiological(CBR)
Englewood Cliffs, NJ(1961) 58)Anon, Warfare, sometimes called: Chemical,
 C 172

Bacteriological(or Germ) and Nuclear War/are. Off, Washington, DC(1960) 15)Anon,

Chemical warfare(CW) may be defined as the ‘ ‘Nonmilitary Defense. Chemical and
tactics and technique of using chemical agents Biological Defenses in Perspective”, Advances
(qv) in offensive action, or of employing in Chemistry Series No 26, ACS, Washington,
defensive measures against such actions(Ref DC( 1960) 16) Anon, “Chemical, Biological
12,p 69) and Nuclear Training Exercises and
Biological warfare(BW) or Biowar may Integrated Training”, FM 3-48(1960) 17)H.L.
be defined as warfare waged by the employment Andrews, “Radiation Biophysics”, Prentice
of biological agents, such as viruses, certain -Hall, Englewood Cliffs, NJ(1961) 18)Anon,
microorganisms, toxic bacteriological products, “Chemical, Biological and Radiological(CBR)
and chemical plant-growth inhibitors to produce Decontamination”, TM 3*220(1961) 19)Anon,
death or casualties in man, animals, or plants; “Chemical, Biological and Radiological(CBR)
defense against such warfare(Ref 12,p 38) Operations”, FM 3.5(1961) 20) Anon,
Radiological warfare(RW) may be defined “Chemical and Biological Weapons Employment”,
as the employment of agents or weapons to FM 3. 10(1962) 21) B. H. Gundel, Ordn 47,
produce residual radioactive contamination, as 435-7(1963) [Discussion on justification of
distinguished from the initial effects of a using CB(Chemica 1 & Biological) weapons in
nuclear explosion(blast, thermal$ and initial warfare ]
nuclear radiation); defense against such warfare
(Ref 12,p 233) Chemical Bombs. Under this name are bombs
For more info on these types of warfare filled with a chemical agent(qv). Some US
see Refs 1-11 & 13-21 chemical bombs are listed in Vol 2 of this
(See also Chemical Agents) Encyclopedia under BOMBS and most Ger
Refs: 1)Refs for Chemical Warfare are the same chemical bombs of WWII are listed in Ref 4
as given under Chemical Agents 2) Anon, Ordn Some fairly recent US chemical bombs
32, 76(Sept 1947)( Biological or germ warfare) are listed in Refs 1,2 & 3, but none is listed
3)T.Roseburg, “Peace and Pestilence”, McGraw or described in the latest edition of ‘ammun-
-Hill, NY(1949) 4) AEC(Atomic Ener~ Commiss- ition Complete. Round Charts’’(Ref 5). The
ion), “The Effects of Atomic Weapons”, McGraw ‘(smoke bombs” described on sheets 13 & 14
-Hill, NY(1950) 5) J. DeMent, USpAppl 729875 of Ref 5 are used for signaling, and for this
(1952); Official Gaz 659, 1104(1952); CA 47, reason are classified not as chemical bombs
978( 1953 )(Radioactive chemical warf are agents) but as pyrotechnic items
6)Anon, ‘ ‘Military Biology and Biological Re/s: 1)Anon, “Chemical Bombs and Clusters”,
Warfare Agents”, TM 3-216(1956) 7)Anon, Dept of the Army Tech Manual TM 3*4f)()(1957)
t ‘Soldier’s Handbook for Nuclear, Biological and (Characteristics, nomenclature and marking
Chemical Warfare”, FM(Field Manual) 21.41 of gas, incendiary and smoke bombs) 2)
( 1948) 8)Anon, “Small Unit Procedures in Anon,. “Bomb, Gas, Nonpersistent, 750-lb,
Nuclear, Biological and Chemical Warfare”, MC-1”, Dept of the Army Tech Bulletin TB
FM 21-40(1958) 9) Anon, “Radiological 3*400(1958) 3) Anon, “Bomb, Fire, 750-lb,
Recovery of Fixed Military Installations”, M116A2”, TB 3400(1958) 4)PATR 2510
TM 3.225(1958) 10)S.Kinsman et al, (1958),pp Ger 14-23 5)Anon, “Ammunition
‘ ‘Radiological Health Handbook”, US Dept of Complete Charts”, Book III, “Bombs,
Health, Education and Welfare, Cincinnati, Pyrotechnics, Grenades, Mines, Cartridge
Ohio(1959) 1 l) ICRP, ‘f Recommendations of Actuated Devices, Rockets, Rocket Motors,
the International Commission on Radiological Demolition Material, Miscellaneous Items of
Protection”, Pergamon Press, NY(1959) Ammunition”, PicArsn, Dover, NJ(1961)
12)Glossary of Ord(1959), 38( Biological
Warfare or “Biowar’ ‘); 69( Chemical Warfare), Chemical Candles. A device(now obsolete)
and 233( Radiological Warfare) 13)Anon, consisting of a thin metal container filIed
“Research in CBR”, Dept of the Army with a them agent and provided with a match
Pamphlet, No 3.2(1960) 14)US Congress, -head which could be ignited by friction or
Senate Committee on Foreign Relations”, electrically. These candles were used both
Chemical-Biological-Radiological Warfare for screening and harassing effects
and Its Disarmament Aspects”, US GovtPrtg- Re/: Hayes(1938), 623
 C 173

Chemical Cannon Shells. See Chemical Gun, and M = wc of mortar, exclusive of accessories,
Howitzer and Recoilless Rifle Shells; also spare parts and tools
Chemical Mortar Shells and Chemical For example, Amer 81mm Infantry Mortar
Rockets has E = 48, while Amer 4.2in(106.7mm) Chemical
Mortar has E = 254( See also table on p 72
Chemical Cellulose. White fibers, consisting of Ref)
mostly of alpha-cellulose$ obtained from Ref: A. M. Prentiss, ArmyOrd 29, 7 1-3(1945)
vegetable matter(such as wood or cotton
linters) by treatment with sulfite dilute NaOH Chemical Energy Ammunition. Ammo.(such as
soln or other reagent. Material obtained by HEAP or HEAT) intended to penetrate armor
treatment of cotton Iinters with dilute NaOH or other resistant targets by them energy
is also known as chemical cotton rather than kinetic energy as in conventional
(See also CELLULOSE AND DERIVATIVES) AP ammo
Ref: Merriam-Webster’s( 1961), 360 & 384 Ref: Glossary of Ord( 1959), 69

Chemical Corps (CC). A branch of US Army Chemical Factors in Propellant Ignition.

having primary responsibility for chemical See M. A.Cook & F. A. Olson, AIChE 1,
warfare matters 39 1-400(1955)
Refs: 1 )Anon, “Chemical Corps Reference
Handbook”, FM 3.8(1955) 2)Glossary of Ord Chemical Fire Starters. Devices intended for
(195 9), 67 3)Anon, “Chemical Service starting fires under adverse climatic con-
Units”, FM 3*85(1960) ditions; such as in wet jungles or on snow
-covered terrain. The Ml fire starter is a
Chemical Cotton. See under Chemical Cellulose cylindrical NC container 1.25” in diam by
3.25” in length filled with 0.802 of
Chemical Destruction of Explosives. These kerosene thickened to a gel and provided
methods rely upon them reactions, which to be with an ignition device, consisting of a
completed require time and full contact of the match-head attached to a disk which covers
expl with the reagent, usually in soln. Chem the filling. A scratcher is attached inside a “
methods should not be used in attempts to metal cap which covers the match head of
destroy expls in large quantities or when any the fire starter. The cap is fastened to the
of the expl items are enclosed or pressed container with adhesive tape(Ref, pp 51-4 &
into components such as detonators. Chem Fig 30). A smaller fire starter, M2, is
destruction methods are suitable for use in designed to be carried in a pocket of the
labs for quantities of expls not greater than Air Force survial kit for use by downed AF
ca 25g cfew in starting fires under adverse climatic
In ~ef 1 are described recommended conditions. This device is a rectangular NC
chemical destruction methods for BkP dr, LA, container, 0.5 xO.5x3’~ contg 0.202 Of
MF & NG. The method described for BkPdr thickened kerosene and provided with an
is the same as given in this Vol under Black igniter which consists of a match-head
Powder,p B 177-R, and methods for destruction mixture with a pull-type scratcher wire(Ref,
of LA are in Ref 2. Destruction of MF will be pp 54-5 & Fig 31)
described under Fulminates and of NG under Ref: Anon, “Ground Chemical Munitions”,
Glycerin, Nitro TM 3~300(1956), 51-5
Refs: I) Anon, “‘Ordnance Safety Manual”,
ORDM 7s224, C3, paragraph 302(1954) Chemical Flame Throwers, See Flame Throwers
2)PATR 2700; Vol 1( 1960),pp A551 &
A573-A575 Chemical Fuels for Rockets. Discussion on
their composition, energy and exhaust speeds
Chemical Efficiency of Mortar can be calcd is given by A. Stettbacher in Explosivst
from the equation: E = (F x W x R)/M, where 1956, 25-33
E = efficiency; F = maximum rate of fire in
rounds per minut~ W = wt of shell filler(HE ) Chemical Grenades. General term for any
in pounds; R = max range of mortar in yds; grenade(hand or rifle) charged with a chemical
 C 174

agent used for casualty, harassing, incendiary purposes are usually classified as pyrotechnic
or screening(smoke) purposes. There are two items. Chemical shells were developed during
types of chemical grenades: a) Burning WWI and used then to a great extent, especially
type which ruptures the grenade body and by the Germans
releases the them filling by a burning action The type of shell used during WWI
(Ref 1, 355 & 357-8; Ret 2,pp 104-5 & Ref 5) consisted of a thin metallic container filled
and b) Bursting type which ruptures the with a chemical(solid or liquid) and provided
grenade body and releases the them fiIIing with a fuze and a booster larger than that in
by bursting of a small chge of HE(such as HE shells of corresponding caliber, ,The
Tetryl) contained in a narrow tube placed in rupture of casing and scattering of them
the center of them filIing(Ref l,p 362; Ref filling were accomplished on bursting of the
2,pp 106-9 and Ref 5) booster(or and auxiliary booster). As all of
Several types of chemicaI grenades used the bursting chge was located in one part of the
by the US Armed Forces during WWII are shell, scattering of them contents was not
listed in Refs 1,2,3,4,6 & 7. In Ref 8, which uniform and some undesirable fragmentation
lists grenades used as late as 1961, there are (instead of just rupture of casing) took place
no chemical hand grenades and only the For these reasons, a new type of them
folIowing three rifIe grenades: a)Grenade, shell was develope d at Pi cArsn sometime after
Rifle, Smoke, WP, filled with 8.480z of white WWI. In the improved type of shell, a long
phosphorous(considered to be obsolete) thin metallic tube(such as of Al), filled with
b) Grenade, Rifle, Smoke, Colored, M22 & a booster type HE(such as Tetryl) was
M22A2 and c) Grenade, RifIe, Smoke, attached to the booster. ,As this tube, called
Colored, M23 & M23A1. Fillers in grenades bur.ster, extends thruout the length of the shell,
b) & c) weigh 6.400z a better rupturing effect and more uniform
(See also Chemical Candles) scattering of them filling can be obtained than
Refs: l)Ohart(1946), 355, 357-9 & 362; Fig with the older type. Very little effect is
203 on p 357 2) Anon, ‘tAmmunition General” produced by fragments of new type of them
TM 9.1900(1.956), 104-9; Fig 3 on p 15; Fig shell since the bursting chge is just
68 on p 104; Fig 72 on p 109) 2a) Anon, sufficient to crack the shell and scatter the
c‘Ground Chemical Munitions “t TM 3s300 chemical filling. In firing them shelis it is
(1956), 27-50(Chemical hand grenades) important that they burst before entering the
3)Anon, *’Grenade, Hand and Rifle, Smoke, ground in order that the chemical be spread
WP, M 34”, Dept of the Army Technical instead of being concentrated in and near the
Bulletin TB 3~300*5( 1958) 4) Anon, “Grenade, shell crater(Refs 1, 2 & 3)
Hand, Irritant, CN-DM, M6A1”, TB ~3~*4, Various types of them artillery shells
(1959) 5)GIossary of Ord(1959), 138 6)Anon, used during WWII are described in Ref 4
“Grenade, Hand, Tear, CS, M7A1”, TB 57 The following currently used US them
(1960) 7)Anon, “Grenade, Hand, Tear, CS, gun, howitzer and recoilless rifle shells
M7A2”, TB 86( 1961) $) Anon, “Ammunition are listed in Ref 5:
Complete Round Charts”, Book III, PicArsn, a)Inc(Incendiary) and HE-Inc shells for 20mm
Dover, NJ, Sheet 20( Grenades) 9)US SPecifi- Guns(Sheet 1)
cations-not found b)WP Smoke for 57mm Gun Ml(obsolete)(Sheet
4)
Chemical Ground Ammunition. Title of the c)WP Smoke for 57mm Recoilless Rifles M18
Department of the Army Technical Manual & M18Al(Sheet 4)
TM 3-300( 1956) d)WP Smoke for 75mm Guns(obsolete )( Sheet
6)
Chemical Gun, Howitzer & Recoilless Rifle e)WP Smoke for 75mm Recoilless Rifle M20
Shells. Artillery projectiles filled with one or (Sheet 7)
several chemical compds designed to produce f)WP Smoke for 75mm Howitzers M lA1 & M3
either casualties such as CWA’S), fires(such (obsolete)(Sheet 8)
as incendiaries) or to screen certain areas g)WP Smoke for 76mm Guns M32 & M48(Sheet 9)
from view(such as smoke-producing compns). h)WP Smoke for 76mm Guns MIAIC & M1A2
Shells conrg smoke compns used for signaling (obsolete)(Sheet 10)
 C 175

i)WP Smoke for 90mm Guns M36, M41 & M54 classified papers) or equipment(such as
(two types of shells)(Sheet 14) filing cabinets) which should be prevented
j )WP Smoke, HD Gas(Persistent), GB Gas from falling into undesirable hands, devices
(Nonpersistent) and HC Smoke for 105mm consisting of sheet-metal boxes filled with
Howitzers M2Al, M2A2 and M49(Sheets 16 & incendiary mixts, such as thermites can be
17) used. ,Several of these devices are described
k)WP Smoke for 105mm Recoilless Rifle M27 in the Ref
(Sheet 18) Ref: Anon, “Ground Chemical Munitions”,
l)WP Smoke with Tracer for 120mm Guns TM 3~300(1956), 55-63
M1A3 & M58(Sheet 21)
m)HD Gas(Persistent), H Gas(Persistent), Chemical Industry; Case Histories of Accidents
GB Gas(Nonpersistent) and. WP Smoke Shells in the. This subject is discussed in the book
(three different types) for 155mm Howitzers published by Manufacturing Chemists Assoc,
Ml, MIA1 and M45(Sheet 22) Inc, Washington 9, DC, Vol 1( 1962)
n)WP Smoke(two types Qf shells), HD Gas
and GB Gas for 155mm Guns M2, M2A1 and “Chemical Kinetics and Chain Reactions”,
M46(Sheet 23) Title of the book by N. N.Semenoff, Clarendon
(See also Ref 6) Press, Oxford(1935)
Note: For meaning of US CW(chemical warfare)
symbols, such as wP, HD, etc, see under Chemical Land Mines. These mines are
CHEMICAL AGENTS usually employed to disperse persistent war
(This section was reviewed by A. B. Schilling) gases from fixed locations. In most cases
R e~s: l)Hayes( 1938), 562-3 2)Anon, they are located together with HE mines in
*‘Ammunition Inspection Guide”, TM 9*1904 mine fields:, None of these mines is described
(1944), 17& 128 3)Ohart(1946), 106& 120 in Refs 1,2 & 4 and only one type, the 1
4)Anon, “Artillery Ammunition”, TM 9*19~1 gallon, in Ref 4, This mine consists of a
(1950), 17,19-20,122-3,131-2,144-6,150,152, rectangular can, 1. lgal capacity contg lgal
159,166-9,185-6,195-8,216-17,222-5 & 240 of liquid such as HD or H(see under CHEMICAL
5)Anon, “Ammunition Complete. Round Chart”, AGENTS) and provided with a burster chge &
Book II, “Artillery Ammunition”, PicArsn(1961) a firing device(electric or nonelectric). The
6)Anon, “Assembly of Explosive Components”, mine is buried slightly below the surface of
TB(Technical Bulletin) 9~1300*203*1( 1961) the ground and can be actuated either by
(Description of: 105mm .Howitzer shell contg pressure of a person stepping on it or by pull
nonpersistent gas GB; 155mm Gun shell contg (or sheer) of a trip wire. ,This action causes
GB or persistent gas VX; 8 inch Howitzer the burster to explode, which is followed by
shell contg either GB or VX gas)(Formula rupture of the mine casing and release of
of VX, is classified) chemical agent designed to harass or poison
enemy personnel
Chemical Hand Grenades. See under Chemical Another US land mine; the 2 gallon, M23,
Grenades described in Ref 4,is filled with persistent
gas VX(formula of gas is classified)
Chemical Howitzer Shells. See under Chemical The use of chemical land mines is now
Gun, Howitzer & Recoilless Rifle Shells very limited and one of the reasons for this
is the possibility of shifting winds blowing
Chemical Ignition. Various chemical igniters them agents into positions of friendly troops
are discussed by A. Stettbacher in NC 9, (This section was reviewed by A. B.Schilling
75-7, 100-1, & 138-41(1938) of PicArsn)
Re/s: l)Anon, “Ammunition General”, TM
Chemical Ignition and Flame Throwers. This 9.1900( 1956)-not found 2) Anon, “Land
subject is discussed by E. C. Kirkpatrick, in Mines”, TM 9~194~ 1956)-not. found 3) Anon,
OSRD Rept 3507(1944) “Ground Chemical’ Munitions”, TM 3.300
(1956), 64-8.. 4) Anon, CC Ammunition Complete
Chemical Incendiary Devices. when it is Round Chart”, Book III, PicArsn, Dover, NJ
requited to destroy by fire, material s(such as ( 1961), Sheet 21-not found 5)Anon, “Mine,
 C 176

Gas, Persistent, VX, 2 Gallon, M23, TB CML by the propellent gases. This mortar was
76(1962) similar to the British 2 inch Bomb Thrower
(Ref 2,p 120)
Chemical Mines. See Chemical Land Mines R efs: l)Hayes( 193.8), 568 la) Anon, “Mortar,
Chemical, 4.2 inch”, TM 3s320(1945) 2)
Chemical Mortar & Chemical Mortar Shells. Ohart( 1946), 120 & 191 3) Anon, “Artillery
Chemical mortar is a weapon(see under Mat~riel and Associated Equipment”, TM
CANNONS) designed to fire shells contg toxic 9.2300( 1949), 78-83 4)Anon, c‘Arrillery
or harassing chemicals , substances producing Ammunition”, TM 9.1901(1950), 122-30,
screening smokes, or incendiaries. These 166-70 & 201-6 5) Anon, “Principles of
shells are called cbem.i.cal mOrtar shells. The Artillery Weapons”, TM 9s3305~ 1( 1956),
term “chemical mortar “ is somewhat obsolete, 160-3 6)Anon, g‘Ammunition Complete .Round
because current US mortars are capable of Cnart”, Book II, “Artillery Ammunition”,
firing, besides expl types of shells, also PicArsn, Dover, NJ(1961), Sheets 5,11,12 &
them types(Refs 1,2 & 4) 20
The most important of these mortars is
the 4.2inch Mortar which is a rifled, muzzle Chemical Mortar, 4.2 i rich; PropelIant for.
-loading weapon(Refs 1, la,3 & 5) capable of The following compn was developed and
firing a chemical shell equipped with a tested at PicArsn during WWII: NC( 13.25% N)
rotating unit which includes a cup-shaped 53.5, NG 43.0, diethylphthalate 3.0 & DPhA
annular disc of soft metal, of the same diam as 0.5%, with methylcellulose 0.03%,. added.
the shell body. Under the action of proplnt It was in the shape of squares 2.2” x 2.2”
gases, transmitted thru a pressure plate, the and 0.013” thick, with one perforation 1.35”
flange of the disc is forced outward into the in diam. Its thermal stability, as judged by
rifling, performing the same function as the 65.5° Surveillance Test and 120° & 135°
rotating band of gun- or howitzer shells. The Heat Tests, was satisfactory
propelling charge consists of NH(non- Re/: W.H.Rinkenbach, pATR 1359( 1943),
hygroscopic) smokeless proplnt, in the form of Table VI
thin discs, The chge is ignited by means of
an igniter cartridge(Refs 1,2 & 4) Chemical Mortar ShelIs. See under Chemical
The following chemical type shells have Mortars & Chemical Mortar Shells
been used in 4.2-in Mortar M30: WP Smoke,
PWP Smoke, H Gas, HT Gas, CK Gas, CG Chemical Munitions. In a broad sense, any
Gas and FS Gas(now obsolete(see Ref 6, and all supplies and equipment required
Sheet 20) to conduct offensive or defensive war by
Note: For meanings of symbols such as WP, means of chemical agents. ,This includes
PWP etc, see under. CHEMICAL AGENTS chemical weapons, chemical ammunition,
There are also TNT shells and Ill transport and fuel, but excludes personnel
(Illuminating) Shells for 4.2in Mortar M30 but and supplies and equipment for purposes
they do not belong to chemical ammunition other than for direct military operations. In a
A smaller, current US mortar, the 60mm, restricted sense, the term means chemical
is a smooth-bore, muzzle-loading weapon ordnance, which includes chemical military
(Refs 3 & 5) capable of firing(besides TNT mat~riel , such as combat weapons with
and Ill shells), one type of WP shell(Ref 6, ammunition and equipment for their use,
sheet 5). Another US smooth-bore, muzzle vehicles, repair tools and machinery
-loading mortar, the 8 lmm(Refs 3 & 5), can (See also Chemical Ammunition)
fire(besides TNT, Comp B, Ill and Inert R efs: l) Anon, “Ground Chemical Munitions”,
shells), three types of WP smoke and two TM 3s300( 1956) 2)Glossary of Ord( 1959),
types of FS shells(Ref 6, Sheets 11 & 12) 192( Munitions) and 202( Ordnance)
During WWII the US Army used a small
(2 inch caliber) mortar(mounted on a table) Chemical Munitions: Destruction, Handling,
provided with a cylindrical shell 6in long, Storing and Shipping. See Anon, “ordnance
enlarged at the head to act as a bourrelet and Safety Manual”, ORDM 7*224(195 1),
filled with a smoke mixt which was ignited paragraphs 2907 to 2937 and Anon,
 c 177

“Ground Chemical Munitions”, TM 3a300 as “buzz” bomb) 2)Ibid, IEC 38, 31O-2O
(1956), 84-6 ( 1946)( Corrosion and stability studies of
hydrogen peroxide-permanganate systems)
Chemical Ordnance. See under Chemical 3)Ibid, IEC 38, 627-30( 1946)( Analytical
Munitions studies and characteristics of the system
hydrogen peroxide-permanganate) 4)Ibid,
Chemical Pots or Smoke Pots. Portable IEC 40, 1320-31( 1948) [Discussion on
containers, usually cylindrical in shape, possibility of ‘using MNMe(mononitromethane)
filled wirh a chemical smoke-producing in liq proplnts for launching “buzz” bombs.
agent. ,They may be subdivided into The great disadvantage of MNMe is its
“burning” and ‘<generator” types. ,The former extreme sensitivity to mechanical action]
type is usually filled with a mixt consisting
of HC 47, ZnO 47 & granulated Al 6%; when Chemical Pulp. pulp prepd by a them process,
ignited it burns with evoln of dense smolce. as distinguished from ‘mechanical” puIp
The latter type usually contains “fog oil” which is prepd by grinding
which is one of the petroleum oils SGF 1 or Ref: Chambers’s Technical Dictionary
SG132; when heated by burning fuel, the “fog Macmillan, NY(1954), 155
oil” vaporizes producing dense smoke
The following US smoke pots are described Chemical Recoilless Rifle Shells. See under
in the Ref: a)Pot, Smoke HC, Ml b)pot~ Chemical Gun, Howitzer and Recoilless
Smoke, 30-lb, M5 c)Pot, Smoke, Floating HC, Rifle Shells
M4A2 d)Pot, Smoke SGF2, An-W and e)Pot,
Smoke SGF 2, Mk 5, Mod 2 Chemical Rifle Grenades. See under Chemical
Ref: Anoq, t ‘Ground Chemical Munitions”, Grenades
TM 30300( 1956), 6-26
Chemical Rocket Engine, A rocket engine that
Chemical Priming. Under the title: ‘(Chemische operates on them proplnts rather than on
Kurz: und Langzeitzihdung”, Stettbacher(Ref ) other energy sources. Chem rocket engines
described various delay action primers activated may be operated by liquid or solid proplnts
by chemical means. Most of these primers R&f: RocketEncycl( 1959), 87-8
were used in sabotage items
R ej: Stettbacher( 1948), 130-2 Chemical Rocket Propulsion and Combustion
Research”. Title of the book by S. S. Penner,
Chemical Problems of Space Flight are discussed published by Gordon & Breach, NY(1962)
by F. Hecht in the “3rd InternAstronautCorgr,
Stuttgart, Ger, Ott 1952 [CA 49, 11286(1955)] . Chemical Rockets. Rockets equipped with
The paper includes a review of new proplncs, chemical warheads. These heads consist
ceramic & high-temperature materials, plastics, of thin-walled casings loaded with casualty
them purification techniques, gas analysis, atm or harassing gas or smoke. ,They may be
research and other problems related to space adopted for point fuzes or base fuzes and have
flight a btmster extending well along the axis of
the head from the fuze seat(Ref 2,p 9)( See
Chemical Projectiles, See Chemical Bombs, also Ref l,pp 9 & 332)
Chemical Grenades, Chemical Rockets and Followirig chemical ground type rockets
Chemical Shells are described in Ref 2: 2.36-in Rockets,
Smoke, WP: M1OA4; -M1OA2 and -MIOAl(pp
Chemical PropelIants. Under this term, Bellinger 41-2). 3.5-in Rocket, Smoke, WP, T127E2
et al describe several liquid rocket proplnts (p 48); 4.5-in RoCkets(Navy)(High Capacity,
which were investigated at the Army Chemi- Smoke FS, and Smoke WP)(pp 53-4); 7.2-in
cal Center, E dgewood Arsenal~ M~land Rockets, Gas: CG, M25(T21) and CK, M27
Re/s: l) F. Bellinger et al, IEC 38, 160-9 (T52),pp 69-70. Only one chemical aircraft
( 1946)(The system hydrogen peroxide rocket is listed in Ref 2. It is 3.5-in Rocket,
-permanganate was found to be suitable for Smoke FS, Mk7 Modifications. Its velocity is
launching the JB-2 flying bomb, also known 1140fps(p 118). Two persistent gas types of
 C 178

rockets are described in. Ref 3 and two smoke, Chemical Wood Pulp. Pulp obtained from wood
WP, rockets; 2.36-in, M1OA2 and 3.5-in, M30 by the sulfite, sulfate or soda process(See
are described in Ref 4 Wood Cellulose under CELLULOSE)
Re/s: l)Ohart( 1946), 9 & 232) 2) Anon,
“Rockets” , TM 9~ 1940( 1950) 3) Anon, Chemische Fabrik Dynamites. This German
“Rocket, Gas, Persistent, CB, l15mm and. Co patented, as NG absorbents, the substances
Rocket, Gas, Persistent, VX, l15mm, M55”, prepd by the method of Parks(based on discovery
TB 73(1961 ).. 4)Anon, “Ammunition Complete of Bielefeldt). These absorbents were prepd
Round Chart”, Book III, PicArsn, Dover, NJ by reacting sulfur monochloride(S2 C12) with
(1961), Sheet No 28 a vegetable oil(process similar to vulcaniza-
tion of rubber by the action of S2C12 on CS2).
Chemical Safety. See under Safety in Chemical The resulting mass, although as elastic and
and Ordnance Plants pliant as rubber, absorbed NG just as well as
kieselguhr. It was claimed that dynamites
Chemical Shells. See Chemical Gun & Howitzer with this ‘~dope” were comparatively
Shells, Chemical Mortar Shells, Chemical insensitive; they could be mixed with PA,
Recctilless Rifle Shells and Chemical Rockets TNT, MF & other expls and used for loading
shells
Chemical Sprays. Liquid sprays from aerial Ref: Daniel(1902), 134
release devices designed to cause harassing
or casualty effects(war gases), screening Chemisorption. It is the chemical phenomenon
(smoke compns), or fire.s(incendiary compns) associated with absorption(Vol l,p A105-L).
Ref: Glossary of Ord( 1959), 69 In chemical adsorption(chemisorption) definite
chemical bonds are produced betw the atoms
Chemical Stability of Explosives and Propel- & molecules on the surface of solid absorbents
lants; Determination of. See Stability of and the molecules or atoms of ‘~adsorbates”.
Explosives and Propellants. Determination of Chemisorption is usually accompained by an
enormous evolution of heat(of the order of
Chemical Stabilizer. A substance added to a tens of thousands kcal per mole) and is
proplnt or expl mixts to reduce them decompn very difficult to reverse. As an example of
during storage. To these belong Acardites(see chemisorption, may be cited adsorption of
Vol l,p A7-R of this Encyclopedia), Centrality, oxygen on incandescent tungsten or of
DPhA(diphenylamine), etc hydrogen & nitrogen by tungsten even in the
cold
.Re/s: l)Kirk & Othmer 1(1947), 217ff; and
Chemical Tests for Explosives and PropelIants. 1st Suppl( 1957), 144. 2)S.J.Gregg, “Surface
See under individual expls and proplnts Chemistry of Solids”, Reinhold, NY(1951),
Chemisorption, 245-70 3)W.E.Garner, Edit,
“Chemical Tests for New Explosives”. Title “Chemisorption”, Butterworths, London &
of NDRC, Div B report by R. McGill, OSRD Academic Press, NY(1957)
787(PBL NO 30778)(1942)
Chemocol. See Chemecol
Chemical Warfare(CW). The tactics and
technique of using chemical agents in Cherenkov(Cerenkov) Radiation is the very faint
offensive action, or of employing defensive emission of a bluish light from transparent
measures against such actions substances(such as glass, water, etc)
(See also Chemical, Biological and Radio- developed in the vicinity of strong radioactive
logical Warfare) sources. This phenomenon, first observed by
Ref:&lossary of 0rd(1959), 69 M-me Curie ca 1910 and later by other workers
in the field of radioactivity, was not under-
Chemical Warfare Agents(CWA). See CHEMICAL stood until P .A.Cherenkov explained it after
AGENTS and under Chemical, Biological and conducting exhaustive studies in 1934-1938,
Radiological Warfare incl. He also developed an instrument t CCheren-
kov counter”) which became useful for research
 C 179

in high energy fields. Investigations on ( 1958),p Ger 4

Cherenkov radiation have been resumed since
1940 by other workers, and an instrument China Clay. The product obtd by leaching
more versatile than Cherenkov counter, called weathered deposits of granitic rocks, so
“photomultiplier”, was developed that quartz & mica portions are removed
The complete mathematical theory and (Ref 1), For example, when Feldspar weathers,
numerous applications of Cherenkov radiation the first product is Cornish stone; this next
in various fields, such as optics, nuclear becomes china clay rock from which the china
physics, high frequency radio techniques, clay is obtd. ,The purest china clay is known
astrophysics and cosmic rays are discussed as kaolin and consists mainly of hydrated
in the Ref aluminum silicate(Ref 2)
Ref: J.V.Jelley, “~erenkov Radiation and Its It is used as an ingredient of some Brit
Applications” , published for the United Kingdom Permitted Explosives, such as Polar Ajax
Atomic Energy Authority, Pergamon Press, NY & Polar Dynobel No 2; and in some US HE &
(1958) pyrotechnic compns
Re/s: l)Hackh’s( 1944), 190 2 )J .H.White,
Cherokee OrdnanceWorks. Ordnance Corps
‘CA Reference Book of Chemistry”, Univ of
field installation located at Danville,
Lend Press, London( 1960), 212
Pennsylvania

Chishokianin. Japan name for 2,3,4 ,6-Tetra-

Chiaraviglio & Carbino Stability Test. Expls nitroaniline. See Vol l,p A4 11-L
are heated at relatively low temps and the
pressure of gases formed on decompn of CHITIN
expl is recorded by a very sensitive Chitin, (CaH1 ~N05)n; mw (203. 19)n, N 6.89%,
manometer(Ref 2). A detailed description of wh solid(when pure); insol in w & in SOIVS
this is given in Ref 1 which dissolve cellulose; decomp to
Re/.s: l)D.Chiaraviglio & O. M. Corbino, glucosamine(also called chitosamine) &
AttiAccadLinceiRend 24, (5a), 120(1915) acetic acid when boiled with coned HC1;
2)ReiHy( 1938), 88 nitrous acid converts it to chito.se. a form of
sugar; treatment with strong alkalies gives
Chicago Ordnance Plant, Ordnance Corps AcOH & cbitosan, a split-product of chitin
ammo plant, Iocated in Chicago 35, Illinois (Refs 4 & 7)
Ref: OrdTech Term(1962), 70 It is a naturally occurring horny
substance which forms the framework of
invertibrates(such as crabs, lobsters & other
Chidite. A mine blasting expl, based on Amm mollusca), and is the animal analog of cellulose
Per.chlorate, used extensively in Canada ca of plants. Chitin is considered a polymer,
1910-20. It was considered preferable to constg of more than 100 units of anhydro-N
dynamites in cold climates because, unlike -acetylgluco samine, a deriv of D-glucose.
NG, it was not adversely affected by freezing. It possesses the same degree of polymerization
The market for this compn was dissipated ca as wood cellulose and has the characteristics
1920 due to the competitive appearance of of polysaccharides
other non-freezing blasting explosives Due to the fact that chitin contains one
Ref: G. F. Smith, Analyst 80, 19( 1955) acetyl group for each CG unit, it can be
deacetylated to a solid prod useful in the
Chikkaen (Navy) or Chikka Namari (Army). prepn of expls. Also because it contains OH
Japan for Lead Azide groups, it may be converted into useful
esters(Ref 7)
Chile Saltpeter. Same as Sodium Nitrate. See l?e~s: l) Beil-not found 2) K. H. Meyer & H.
under Nitrates Wehrli, Helv 20, 353-62(1937) & CA 31, 5807
( 1937)( Chemical comparison of chitin with
Chil worth Special Powder or Chil worth cellulose) 3) G. A.Hill & L. Kelley, “Organic
Smokeless Sporting Powder. See Amide Chemistry”, Blakiston, Philadelphia 1944),
Powder, Vol l,p A168-R and PATR 2510 191 4)Hackh’s( 1944), 191 5) J. T. Marsh &
 C 180

F. C. Wood, “An Introduction to the exploded when heated rapidly; insol in

Chemistry of Cellulose”, Chapman & Hall, perchloric acid(Ref 3)
(1945), 106-7 6)Karrer( 1950), 349 7)Kirk Deacetylated chitin can be prepd by the
& Othmer 11(19s3), 10 & 2nd Supplement method of Rigby(Ref 3) which consists of
( 1960), 222-27 8) Fieser & Fieser(1956), heating at 110° for 4hrs, shrimp, lobster or
388-89 crab shells(previoulsy washed by success iv&
Nitrated Chitin or Chitin Nitrate, [ C6H702- treatments with boiling 1% NaOH soln, 5%
(ON02)2.NH.C0.CH3 ] n; mw (293.19)n, N HC1 soln & Na2C03 soln contg some soap)
14.33 %( found 7,5% nitrate N); wh fibrous with 40% NaOH soln. This method was checked
flakes, ignites ca 163° & burns vigorously; & confirmed by Meyer & Wehrli(Ref 4) and
thermally stable by Abel Test; insol in , WOIfrom et al(Refs 5 & 6). It is claimed that
most SOIVS; partially sol in formic acid(from this treatment does not degrade the product
which it is repptd by w); sol in coned in regard to polymerization
H2S04 or HCl(from which it is not repptd by The Percblorate salt, of 85% deacetylated
w); various org SOIVS such as benz, tetralin, chitin, a cream-colored, granular, free-flowing
aniline, nitrobenz, phenol, pyridine & furfural expl product(with an acid content of 96%
cause it to swell; it is completely denigrated theoretical, calcd as perchloric acid), was
by NaSH in 3 hrs at 16°(Ref 3) prepd by Wolfrom et al(Ref 6) by a method
This compd was first obtd by nitrating considered an extension of the method
chitin with coned HN03(d 1.50); the chitin described by Hofmann et al(Ref 2). This salt,
dissolved after l-2hrs at RT and soln was sol - in 100% HN03, detonated(leaving
poured into a large amt of cold w(Ref 3). considerable carbon residue) when heated
The product contained 7.5% nitrate N, confined over an open flame
indicating that only 1.5 instead of 2( OH) Re/s: l) BeiI-not found 2)K.A.Eiofmann et al,
groups had been esterified. Earlier, Ftirth & Ber 43, 1080(1910) 3)G.W.Rigby, USP
Scholl(R~f’ 2) treated chitin with fuming 2040879(1936) & CA 30, 4598( 1936) 4)K.
HN03 and obtd two products, one of them Meyer & H. Wehrli, Helv 20, 353( 1937) & CA
insol in ordinary SOIVS while the other was 31, 5807( 1937) 5)M.L.Wolfrom et al, JACS
sol in ale, acet, ethyl acetate, acetic acid 65, 2084( 1943) 6)M.L.WO1 from et al, Ohio
but insol in eth. It was claimed that both State Univ Final Rept, Project 459, Columbus,
products were nitro-esters of chitin but no Ohio(Jan 1953)pp 1,3 & 34
furrher investigations were made. .Shoruigin & Nitrated Deacetylated Chitin. A wh flocculent
Hait(Ref 3) claimed the 1st prod(insol) was ppt contg 11.6 to 11.9% nitrate N(as detd by
chitin nitrate while the 2nd prod consisted of DuPont nitrometer; obtd by Wolfrom et al(Ref
oxidized products of decompd chitin. Meyer & 3) by nitrating deacetylated chitin with 100%
Wehrli(Ref 4) also prepd nitrochitin as well HNOa. The nitrated product represented the
as other derivs of chitin. According to M & W, combined nitrate salt & nitrate ester of
the additive derivs of chitin with mineral deacetylated chitin. This substance
acids are not homogeneous compds but mixts contd one nitric acid salt unit per anhydro-
of polyglucosamines n-glucosamine unit and 1.60-1.65 nitrate ester
Re/s: l) Beil-not found 2)0.vonFiirth & E. unit per anhydro-o-gluco samine & anhydro
Scholl, BeitrChemPhysiol 10, 188-98( 1907) -N-acetyl-D’-glucosamnine units. Attempts to
& CA 1, 3020( 1907) 3)P.P.Shoruigin(or nitrate deacetylated chitin by means of
Schorigin) & E.Hait, Ber 67, 1712-14(1934) nitrogen pentoxide, in a non-aqueous medium
& CA 29, 473(1935) 4)K.H.Meyer & H. Wehrli, “k in the presence of sodium fluoride, by the
Helv 20, 353-62(1937) & CA 31, 5807(1937) method of Caesar(Ref 2) were unsuccessful
Chitin, Deacetylated. A product which has mainly because of occlusion of NaF in the
lost ca 85% of the N-acetyl groups of natural nitrated products(Ref 3)
chirin; small creamy to it-tan flakes; sol in The nitrated deacetylated chitin was
dil aq solns of AcOH(repprd by neutralization); insol in w or acet but sol in a 1:1 mixt of the
sol in w or ale; S1 sol in 98-100% HN03 two. On heating in a test tube over an open
(0.30 gm dissolved in 20g HN03 at 300); flame, it decompd with a puff leaving a con-
when irs soln in HN03 was poured into ice siderable amt of carbon residue
water, a wh flocculent ppt was obtd which Its Percblorate salt, contg 11.4% toral N,
 C 181

7.1% nitrate N & 26.1% perchloric acid, was A very large number of chlorates are
prepd by Wolfrom et al(Ref 3) by nitrating, known and they may be divided into inorg &
with 100% HN03, the perchlorate of deacetylated org chlorates. Inorg chlorates of alk or
chitin(See above). ,,The salt so prepd was alkaIine earth metals are prepd either by
insol in either acet or w but completely sol in action of chlorine on hot alkali or by
6:1 or 1:1 acetone-w. ,The material decompd electrolytic oxidn of the chloride ion. For
with a burst of flame, leaving no residue, the prepn of org chlorates, such as pyridine
when heated over an open flame chlorate, a pyridine base is treated with an
Re/s: 1)Beil-not found 2) C. V. Caesar, USP aq soln of HC103. Kirk & Othmer(Ref 8),
2400287(1946) & CA 40, 4487(1946); JACS Gmelin(Ref 3) & others describe various
68, 372(1946) 3)M.L.wolfrom’ et al, Ohio methods of prepg chlorates. See also under
State Univ Final Rept, Project 459, Columbus, various chlorate compds des~ribed below
Ohio(Jan 1933) Chlorates mixed with combustible materials
may form expl compns. For example$ an expln
Chloramine or Chloramide (Monochloramine), can occur if a chlorate is mixed with org matter,
NH2C] ; mw 51.48, N 27.20%; CO1 oil with a charcoal or sulfur and the mixt is struck with
strong ammoniacal odor; fr p -66°, very a hammer or heated. In the expl industry,
unstable as it is decompd with expl violence chlorates are used as oxidg agents in combina-
by heat or agitation, sol in water. It can be tion with MF, phosphorus, antimony sulfide &
prepd by the action of ammonia on Na hypo- other combustible substances for primer cap
chlorite or dil hypochlorous acid compns. ,They are also used in pyrotechnic
Chloramine was widely used in the compns for flares & aerial bombs, and as a
treatment of water supplies between 1930-44 component of permissible expls. ,Chlorates,
but many water plants have abandoned this as well as perchlorates, are used extensively
treatment to-day. It has bactericidal props, in the manuf of Cheddites(qv)
but against many organisms its action is much Re/s: l)R.Escales~Chloratsprengstoffe~
weaker than free chlorine. This compd can Viet & Co, Leipzig( 1910), l-62(Historical
react, under alkaline condition, with excess description of chlorates & chlorate expls)
ammonia to form hydrazine 2)Mellor 2( 1922), 296ff 3)Gmelin, SystNr 6
Re/s: l)Gmelin, SystNr 6(1927), 418ff 2) (1927), 307-62 4)Ullmann 3 2nd ed (1929),
Mellor.8(1928), 6.04 3)Davis(1943), 427 4) 278-307; 5, 3rd ed (1954), 525-42 5) Thorpe
Hackh’s(1944), 192 5)Kirk & Othmer 3(1949), 3(1939), 66ff 6)Mellor(1939), 512 6a)I.F.
665 6) E. Colton & M. M. Jones, JChemEduc Blinov, “Chlorate and Perchlorate Explosives:’
32, 485-87( 1955)(A review of the chemistry of Oborongiz , Moscow( 1941) 7)1.Kabik, US
monochloramine) 7) CondChemDict( 1961), 252 BurMines Info Circ 7340(1945) & CA 41, 4311
( 1947)(Hazards from chlorates & perchlorates
oa & ma Chloranilinium Pentazidodicuprates, in mixts with reducing materials) 8)Kirk &
C6H4C1NH3 [ Cu2(N~)5 ] ; exp compds which .Othmer 3(1949), 707ff 9)Sax(1957), 459
darken at 80° and explode at 210-13°. See 10)T.A.Rodgers & C. J. Wassink, “Studies of
Cupric Azide Complexes, & Ref 16 in Vol l,p Thermal Decomposition of Chlorates and
A533-R Perchlorates at Constant Temperatures and
Pressures”, Univ of Ark Final Summary Rept
CHLORATES (1958 )(Dept of Army Contract No DA-23-072
Chlorates. Compounds formed from chloric -ORD. 1049) 10a)R.G.Hall, USP 2841481
acid(HClC)3), by combination of the mono- (1958) & CA 52, 17716( 1958) (Stable pyrotechnic
valent radical -C103 & a metal, hydrogen or compns are obtained by mixing a liq phenol-,
other radical, are called chlorates. The urea-, or melamine-formaldehyde condensation
chlorate salts are crystalline & some are product and a 120-mesh oxidizing material
deliquescent; they are decompd by heat such as an Amm, alkali metal or alk-earth
with evolution of oxygen; sol ii water; and metal chlorate, perchlorate or nitrate or
are powerful oxidg agents. The principal urea nitrate in a .1:1-3 ratio and polymerizing
toxic effects are the production of for 3mins at 80-100°) ll)F.A.Warren et al,
methemoglobin in the blood& destruction of C<Chlorates and PercJdorates Their Manufacture,
red blood corpuscles Properties and Uses”, NAVORD Rept 7147
 C 182

(Vol l)(1960)(Contract NOrd 18471) 12)F.A. (such as chlorine, hypochlorite, etc) interfere
Warren et al, “Chlorates and Perchlorates (Ref l,pp 243-4 )(See also Ref 8, vol 2,p
Their Characteristics and Uses”, NAVORD 267-8)
Rept 7147(V01 2)( 1960)( Conf)(Not used as a f)Other calorimetric and spot tests. See Refs
source of info) 1,4,8 & 9
g)Testing of samples suspected to contain
Chlorates, Analytical Procedures. Following chlorates, chlorides or perchlorates. Acidify
are some tests for chlorate ion: the aq s oln of sample S1ightly with nitric
A. Qualitative Tests: acid and add an excess of Aq nitrate soln.
a)Testing by heating with H2S04. Place a Formation of ppt of AgCl indicates the presence
few mgs of solid material in a Pt crucible, of a chloride. Boil the slurry and filter off
add a few drops of coned H2S04 and heat with the coagulated ppt. To the clear filtrate add a
a flame; an expln accompanied by evoln of few mls of 40% formaldehyde and boil to reduce
yel fumes indicates a chlorate(Ref 5,p 262) the chlorate to chloride. Add an excess of
b)Spot test with MnS04 +‘ H3P04. ,This test Ag nitrate and allow to stand on a steam bath
described by Feigl(Ref 9) is applicable for for lhr, while the mixt is protected from light.
testing expls. It is based on the formation of Remove ppt of AgCl by filtration and evap
complex Mn+++ ions when a chlorate is the filtrate(in a dish) to dryness and the
treated with MnS04 in a coned phosphoric disappearance of nitric acid odor. Cool the
acid soln: dish and transfer the ppt, using a small amt
CIO~ + 6Mn+++ 12P04--= 6Mn(P04)2--+ C1-+3H20. of w, to small pt crucible, Dry the contents by
The resulting color is more or less violet heating and fill the crucible near the top with
depending on the chlorate content. Very pale anhydrous Na carbonate or with Amm chloride.
colors may be intensified by adding a drop Fuse the mass, cool it and dissolve in dil
of an alc soln of diphenylcarbazide. Limit of nitric acid. ,Add an excess of Aq nitrate soln
sensitiveness is 0.00005mg and, if ppt of AgCl forms, the presence(in
c)Color test by aniline. It is one of the oldest original sample) of perchlorates is indicated
methods and depends on the formation of a (Ref 3,pp 14-15)
blue coloration when a soln of aniline in coned Note: Other reducing agents than formaldehyde
H2S04 is added to an aq soln of sample. (such as Zn in an acid, sulfur dioxide or
Several modifications of the original method ferrous sulfate) may be used(Refs 5,6,7 & 11)
are known. Aniline sulfate may also be used B. Quantitative Tests
for the quantitative detn of chlorates(Ref l,pp a)Reduction with formaldehyde. This test,
243-4; Ref 8, vol 2,pp 266-7) essentially the same as qualitative test (g)
d)Method of Denig~s. Place in a small test was used at the USBurMines explosives
tube 2 drops of test soln and add gradually, laboratory at Bruceton, Pa. It is an accurate
with stirring and cooling under tap w, 2ml method, but rather time consuming. A detailed
of H2S04. Then add without stirring 5drop.$ d~scription of the test is given in Ref 3,pp
of resorcinol reagent(prepd by dissolving lg 63-4(See also Ref 5,p 1677)
of re sorcinol in 10drops of H2S04 ) and swirl b)Reduction with sulfur dioxide. This test
the tube gently while cooling it under tap w. described by Gody(Ref l,p 245) and by Storm
Green color indicates a chlorate. If the color (Ref 3,pp 62-3), has been used at the
is too intense, dil the soln with w. Limit of ButMines. ,For this procedure, treat an aliquot
sensitiviness is 0.0000 lg. ,Nitrites interfere part of the w extract of an explosive(pre-
giving blue color, but this can be overcome ferably contg not more than about 0.50g of
by using a modified procedure described by chlorate ) with a current of sulfur dioxide
Gody(Ref l,p 244) (such as provided by a small cylinder of liq
e)Method of Lafitte. Add to test soln a few S02 ) and regulate the current by means of a
drops of aq aniline(l:40) and then HCl(d valve in such a manner that no excessive
1.18), twice as much by vol. A red-violet rise in temp of the reaction vessel is observed.
color developes immediately but this changes Continue this opn until a strong odor of S02
to dark blue and then to green. As little as persists in the soln after stopping the current
0.0006g of chlorate can be detected in a satd and blowing across the surface of the liquid,
soln of K nitrate, but many oxidizing agents After complete saturation with S02, boil the
 C 183

liq to remove any traces of S02 and then add a detn of chlorate and perchlorate in presence
few nils of H202 soln, which oxidizes the of each other was re-cently described by
last traces of S02 to SOS. Acidify the soln DeSousa(Ref 12). In this method one portion of
with a few drops of HN03 and det the chloride the sample, together with 12 times its wt of
(resulting from the reduction of the chlorate) NH4CI, is heated in a Pt dish, covered with
by pptn with Ag nitrate soln and weighing as a ribbed watch glass, for l-2hrs, just below
AgCl the fusion pt of residual chlorides(in order
Complete removal of S02 from the soln is to avoid damage to Pt dish). This operation is
necessary in order to prevent reduction of the repeated with addnl amt of NH4C1. ,~e chlorates
Ag nitrate and perchlorates are reduced to chlorides. The
(See also Ref 5,P 274) second portion of sample is boiled, while
c)Reduction with ferrous sulfate. .See Ref 5~PP stirring, for 15mins with 10% FeS04 soln in
274 & 1677; Ref 6, Vo.1 2,pp 390 & 565; Ref oder to reduce chlorates, leaving perch lorates
ll,pp 607-9 and Ref 15,pp 313 & 571 unchanged. Then the 1st portion is dissolved
d) Ferrous ammonium sulfate. See Ref 5,p 2160 (after coolifig) in w acidified with HN03 and
e)Reduction with zinc in acetic acid. See Ref an excess of AgN03 soln is added to ppt
5,pp 275,276& 1677; Ref 6, Vol 2, p 391 chlorides as AgC1. At the same time the 2nd
f)Reduction with Devarda’s alloy. See Ref 6, portion is cooled, acidified with HN03(until
Vol 2,p 391 the basic ferric salts are redissolved) and
g)Reduction by ignition with ammonium treated with an excess of AgNO~ as abov~
chloride. See Ref 6, VOI 2,p 391 After filtering each portion separately thru
h)Reduction with hydrochloric acid. See Ref 6, Gooches and washing the AgCl ppts, first with
Vol 2,pp 599 & 601 0.1% AgN03 and then with 1% HN03, they are
i)Reduction with bromide in the presence of transferred, without drying, to 1 liter beakers,
hydrochloric acid. See Ref 15,pp 361-2 each contg sufficient amt of ammonical O. lM
j)Reduction with iodide in the presence of potassium nickel cy%nide soln to satisfy the
hydrochloric acid. See Ref 15,P 361-2 reactiop: 2AgCl + K2Ni(CN)4. 2KAg(CN)2+ NiC12
k)Titratlon with standard mercurous nitrate
The’ O. lM K2Ni(CN)a soln is prepd by
solution. See Ref 15,p 399
titrating 1 mole KCN dissolved in ca 500ml of
The following procedure described in
w contg ammonia, with O. lM NiS04 soln until
Ref 6, Vol 2,p 390, is accdg to Ref 11,
murexide indicator(satd soln of Amm purpurate,
applicable for analysis of the pure chlorates made fresh daily) changes from yel to purple.
of Ag, Al, Amm, Ba, Ca, Cd, Cs, Cu, Fe, K, Li,
Then the soln is diluted to 1 liter
Mg, Na, Ni, Pb, Rb and Zn
As soon as contents of beakers are
Procedure: Dissolve a 0.3g sample in 100ml
completely dissolved} the solns are diluted to
of w, add 50ml of 10% soln of FeS04.7H20,
ca 500m1 and titrated, in presence of murexide
heat. with const stirring to boiling and maintain indicator, with O. lM disodium ethylene-
for 15mins. Cool, add sufficient amt of HN03
diaminetetraacetate( EDTA) to chge of color
to dissolve the basic ferric salt, and then an
from yel to purple. Each ml of O,1OOM EDTA
excess of AgN03 soln. After allowing the ppt
corresponds to 16.691mg CIO~ and 19.891mg
of AgCl to settle in a dark place, filter thru
Clo:
a sintered glass crucible, wash with w and
(See also Refs 2,4,10 and under individual
dry, first at 100° and then at 130°, to const
chlorate s.)
wt. One gram of AgCl corresponds to 0.8550g Re/s: l) Gody( 1907), 243-4 (Co10rimetric tests
KC103 for chlorates) 2)Escales, Chloratspr(1910),
Accdg to Ref ll,p 608, this analysis is 45-8( Qualitative); 48-51 (Quantitative); 51-2
not applicable to chlorates of Co, Au, Cr, Mn (Detn of impurities in chlorates); 72-4( Tests
and probably Hg. ,This is because they offer for ,chlorates in BkPdr) 3) C. G. Storm, ‘tThe
possibility of cationic interference in the Analysis of Permissible Explosives”, US
reduction step. ,This interference can be ButMinesBull 94(1916), 14-16 & 62-4 4)
overcome by reducing chlorate to chloride by Gmelin, SystNr 6(1927), 351-62 5)Scott &
ignition with Na2C03 or NH4C1 followed by Furman(1939), 262,274-6,1677 & 2160 6)
detn of resulting chloride by pptn with AgN03 Tre.adwell & Hall 2(1942), 390-1, 565,599 &
A volumetric method for simultaneous 601 7)Kast-Metz(1944), 464 8)Welcher 1
 C 184

(1947), 144, 181& 382(Detns with ~-naphthol, dioxide, C102; and when heated rapidly, it
resorcinol or formaldehyde); 2(1947), 266-7, dec without expln, forming chlorine, basic
322,354,421 & 441( Detns with aniline, perchlorate & oxide
benzidine ~-naphthylamine, @-naphthylphenyl- Al chlorates not only act as oxidg agents,
amine & phenyldihydrobenzoacridine); 3(1947), but also due to w of crystallization, as
39 &445(Detns with pyridine&diphenyl- cooling agents in proplnts
carbazide); 4(1948), 187,270,508 &520(Detns Refs: l)D.K.Dobrosserdoff, ZhRusFiz-Khim-
with thiourea, brucine, strychnine, indigo Obshch 36, 468(1904) 2)Mellor 2(1922), 353
carinine & methylene blue) 9) Feigl 1(1954), ‘3)Gmelin, SystNr 6(1927), 338 & 342 4)
274-5 &300(Spot tests); 2(1956), 484(Spot Ullmann 3(1929), 297 5) Anon, US War Dept
test for chlorates in expls) 10)E.A.Burns, Tech Manual TM 3*250(1940), 36, { ‘Stosage
‘%pectrornetric Determination of chlorate and Shipment of Dangerous Chemicals” 6)
Impurities in Ammonium Perchlorate”, Cal- CondChet@ict( 1950), 30(Not listed in 1961
TechProgress Rept 30.12(1959), Contract No edit) 7)Sidgwick, Chem Elems 1(1950), 428
NASW-6 ll)F.A,Francis et al, “Chlorates 8)Sax( 1957), 261 9) F. A. Warren et al, “Chlorates
and Perchlorates”, NAVORDRept7147(Vol 1) and Pert.hlorates”, NAVORD Rept 7147(Vol 1)
(1960), 607-10 12) A. D.. de Sousa, Chemist (1960), 139
Analyst 49, No 1, 18(1960 )( ’’Determination of
Chlorate and Per.chlorate in Presence of Ammonium Chlorate, NH4C103; mw 101.50,
Each Other”) 13)H.Laub, ZAnalChem 173, N 13.80%; wh trysts, mp sublimes &
208-10(1960)&CA 54, 16254( 1960) (Sepnof explodes 70-100 °(depending on rate of heating
various anions, including CIO~, by paper & sample size); accdg to Kast(Ref 7,p 208),
chromatography) 14)1. I. M. Elbeih & M. A.Abou Salvadori reported mp 60°; sol in w; heating
-Elnaga, AnalChimActa 23, 30-5(1960)&CA aq soln above 75° causes spontaneous
54, 18195 (1960)(A new scheme of analysis for decompn; sol in AcOH & aq ale; nearly insol
the common anions, including CIO~ based in abs ale. Was first prepd by Gay-L ussac in
on paper chromatography) 15)Vogel, 18’15 from aq HC103 & NH40H or(NH4)2C03.
InorgAnalysis(1961), 313,361-2, 399& 571 It can be prepd also by treating a soln of
Amm silicofluoride with KC103 or by the
Chlorates, Destruction of. One of the simplest reaction of (NH4)2C0,3 & Ca(CIOa )Zor Ba(c103)2
methods for destruction of a chlorate is to (Refs 3 & 5). ,Gelhaar(Ref 1) prepd the salt by
treat the sample with coned HC1, followed by neutralization of aq HC103 with NH3 and
evaporation to dryness evapn of the w; he thoroughly examined its
Re/: Scott & Furman(1939), 907 props(See below under Explosive Properties).
Fairbrother(Ref 4) reptd that a cold satd soln
List of Chlorate Compounds of NH4C103 appears to undergo no decompn
Aluminum Chlorate, A1(C103)3. The anhyd when kept indefinitely; if any solid phase is
salt could not be prepd. Attempts to prep it present decompn occurs in a few days
by heating the hydrates always led to explns. Ammonium chlorate is an expl compd. It
This compd exists as hexa- and ennea is highly dangerous and can explode when
-hydrates: Hexabydrate, A1(C103 )3.6H20; mw shocked or exposed to heat(Ref 13). Potjewijd
385.44, COI hygr rhombohedral trysts, mp dec (Ref 10) reported that a drum of weed killer
or expl > 100°; can be prepd by treating a (100 kg) exploded with violence on the premises
hot soln of Ba or Ca chlorate with a soln of of a hospital. It was suspected that NH4C1
A12(S04)3. After filtering the ppt of Ba or had been added to the KC103 resulting in
Ca sulfate, the filtrate must be evapd by formation of NH4C103
heating in a desiccator contg coned H2S04. Explosive Properties were detd by Gelhaar
If the evapn is done in the cold, the (Ref 1), Nao~m & Aufschltiger(Ref 6), Kast
Ermeuhydrwte, A1(C103)3.9H20, is obtd. It (Ref 7) etco Bri.sarzce: by Kast’s Formula,
is sol in w, eventually forming a basic salt 19.8x 10S(TNT 86.1 x 106) and by Cu Crusher
on standing; also sol in alc & in dil HCI. Test 1.5mm at d 0.9( TNT 3.6mnl at d 1.59)
According to Dobrosserdoff(Ref 1), when a (Ref 7) Detonation Velocity: 3300m/sec at
hydrated Al chlorate is slowly heated, it d 0.9(Ref ?) Explosion Temperature: expl
decomposes & explodes forming chlorine at 94° in 7mins at 100° in 3.5mins & 107°

.
 C 185

in 2mins(Ref 1); 102°(Ref 5); when heated in Ammonium Chlorate, Analytical Procedures.
a sealed capillary tube, it expl with noise Chlorate ion may be detd by methods outlined
(Ref 7) Friction Sensitivity - decrepitates under Chlorates, Analytical Procedures, while
when rubbed in a porcelain dish(Ref 7) Gas ammonium ion may be detd as outlined under
Volume: 82X8 l/kg(Refs 1 & 7) Heat of Expln Ammonium Chromate, Analytical Procedures
(Qe): 441cal/g(Ref 1); 468cal/g(Ref 6) & (under CHROMATES)
4S9cal/g(Ref 7) Heat o/ Formatiorz(Qf); There is no US Specification for
64kcal/mol or 620cal/g(Ref 7) Ignition: Ammonium Chlorate
can be ignited by gas flame or BkPdr fuse(Ref Amm chlorate, usually present in tech
46) Impact Sensitivity with 2kg wt 15cm(Ref Amm perchlorate, is art undesirable impurity
1) & 20cm(Ref 7) bzitiation Sensitivity - See if the material is intended for use in expl or
Sensitivity to Initiation Power, by Trauzl pyrotechnic compns. This is because Amm
Test,254cc(Ref 1); 240cc(Ref 6) and 245cc chlorate lowers deflagration temp and impairs
(Ref 7) Sensitivity to Initiation-can be detonated the stability of Amm perchlorate. For these
by a std blasting cap, but it is preferred to use reasons, only small amts of chlorates are
cap & booster(such as PA)(Ref 7) Stability in usually tolerated, such as 0.02%( calcd as
Storage is unsatisfactory; when stored at RT NH4C103) in Amm perchlorate intended for
it decomp slowly leaving AN as a residue and use in US rocket proplnts, tracer ammo and
not the chloride or perchlorate as would be flame throwers(Ref2,pp 2 & 6)
expected(Ref 8); when stored at above RT or As only traces of Amm chlorate are
in closed containers, ignition or spontaneous present in Amm perchlorate, a calorimetric test
expln may occur(Refs 2 & 9) can be used, such as by means of brucine
Uses: Because of its unsatisfactory stability -sulfuric acid reagent(Ref 1) or by ortho
and high sensitivity to mechanical action, it -tolidine reagent(Ref 2)
cannot be recommended for use in military expl Refs: l)C.Eger, AnalChem 27, 1199-1200
or pyrotechnic compns. Nevertheless, the (1955) & CA 49, 13835(1955) 2)US Military
Japanese Navy used it during WWII in an Specification MlL.A.192A( 1)( 1961), 4
(Ammonium Perchlorate)
exP1 of unknown name which consisted of
NH4C103 51.5, Ba(N03)2 34.5, woodpuip 5.0
and oil +” TNN 8.2parts(Ref 12). Another” Anilinochlorates, See Vol l,p A406-R of this
example is the expl patented by Billwiller(Ref Encyclopedia, under Salts of Aniline with
11): mixt of NH4C103 with naphthalene, Inorganic Acids
paraffin wax and/or lubricating oil; it could be
-.
Initiated, when confined, with thermite. .Accdg to Barium Chlorate, Ba(C103)2, mw 304.27; CO1
Ref 5, NH4C103 was used in some Ger trysts, mp 414 °(dec); begins to evolve
detonators and in blasting expls contg liquid oxygen at 300°; decrepitates or dec.omp
TNT violently when heated rapidly; Qf 18 lkcal/mol.
Refs: l) J. Gelhaar SS 11, 166-7(1916) 2) Can be prepd by dehydrating the monohydrate.
Clover( 1918), 280 3)Mellor 2(1922), 338 Monobydrate, Ba(C103 )2 .H20; mw 322.29;
4) F. Fairbrother JACS 44, 2419-22( 1922)& CO1, non-hygro monoclinic trysts; mp begins
CA 17, 37( 1923) 5)C. A. Taylor & Wm.H. to loose H20 at 120°, evolves O at 3000;
Rinkenbach, US BurMinesBull 219(1923), d 3.179; n~ 1.562 at 20°; sol in w [22.8g of
3.6-7 6)F.Naodm & R. Aufsch12iger SS 19, Ba(C103)2 in 100g of w at 0°, 37 at 20°,
123(1924) 7)H.Kast, SS 21, 208-9(1926) & 77.5 at 60° & 126.4g at 100° ] (Ref 5b); S1
2?, 8(1927) 8)Gmelin, Syst Nr 6( 1927), 337 sol in alc or eth. It was prepd in 1802 by
& 342 9)Ullmann 3(1929), 297 10)T. R. Che,nevix and in 1815 by L. N. Vauquelin
Pot jewijd, PharmWeekblad 72, 68-9(1935) & by passing chlorine into w in which Ba
CA 29, 1985(1935) ll)J.Billwiller, l?rP hydroxide or carbonate was suspended.
862323(1941) & CA 42, 9180(1948) 12) Present methods of prepn include electrolysis
Anon, “Handbook of Japanese Explosive of hot BaC12, saturation of a hot aq soln of
Ordnance”, OPNAV 3@3M ( 1945), 32 13)Sax Ba(OH)2 with chlorine, or reaction of BaC12
(1957), 275 14)17.A.Warren et al, “Chlorates & Na chlorate(Refs 12345
$!?$ & 8)
and P erchlorate.s”, NAVORD Rept 7147 Ba chlorate is a very powerful oxidg agent
(Vol 1)(1960), 139-40 and is dangerous when mixed with org
 C 186

compds, especially hydrocarbons 2)Me110r 2(1922), 344 3)Gmelin, SystNr 6

Uses: Ba chlorate has been used in some (1927), 337 & 339 4)Ullmann q 1929), 297
primer and igniter compns(Ref 15,P 255), but 5)Melior(1939), 514 5a)Davis(1943), 70,72,
more often in pyrotechnic compns. In these 86& 119 5b)Kast-Metz(1944), 513-14 5c)
mixts, Ba chlorate not only supplies the Weingart, Pyrotechnics 1947), 133 & 146
oxygen required for combustion but also imparts 6)B.P.Seipel, ChemAnal 38, 81-3(1949)&
to the flame the characteristic green color of CA 44, 2400( 1950)( Laboratory prepn of Ba
Ba compds. Most of its uses were for green chlorate) 7)R.F .Barrow & E. F. Calvin,
light pyrotechnic compns used for signaling ProcPhysSoc(London), 32B, 32-9(1949)&
purposes, such as: a)Rocket green signal CA 44, .939( 1950) 8)Kirk & othmeq 3
compn: Ba chlorate 55.5, Ba nitrate 33.3 & (1949), 715 9)CondChemDict( 1950), 82
orange shellac 11.2%(Ref l,P 159) b)Green 9a)Izzo, Pirotecn~a(1950), 211-12, 227 &
rifle light and green V~ry light. compn: Ba 2.29 10)Sidgwick, ChemElms 1(1950), 258
chlorate .90 & orange shellac 10%(Ref l,P 10a)Shidlovskii( 1954), 22-3, 27-8, 67, 118,
159) c)Green position light compn: Ba 149 & 194-5 1 l)P.Retny-Gennet~ & G.
chlorate 23.2* Ba nitrate 59.0~ K chlorate 6.3, Dur~nd, BuHFr 1955, 1059-60 & CA 50,
otange shellac 10.5 & stearin l%(Ref l,p 1419( 19s6)(Soly of Ba chlorate in ale-w
.159) d)Green light compn: Ba chlorate 40* rnixts) 12)Sax( 195.7), 331 12a)PATR 2510
Ba nitrate 50 & shellac 10%(Ref 7) e)Ital (1958),P Ger 154 13) F.A.Warlen et al,
green light: Ba chlorate 70, shellac 17 & C‘Chlorates and Perchlorates”, NAVORD
lactose 13!%(Ref 9a, P 211) f)Ger green star Rept 7147(V01 1)(1960), 140 14) CondChem.
signal: B.a chlorate 64, K chlorate 18 & Dict( 1961), 125-6 15)Ellern, Pyrotechnics
shellac 18%(Ref 9a,p 211 & Ref 12a,p Ger 1961), 56, 97, 99 & 255
154) f)French green star: Ba chlorate 85,
carbon 3 & shellac 12%(Ref 9a,p 227) g)Fr Barium Chlorate, Analytical Procedures.
green star with parachute: Ba chlorate 90, Chlorate ion may be detected and detd as
castor oii(or vaselin) 2 & accorides gum 8% described under Chlorates, Analytical
(Kef 9a,p 227) h)Ger green stat: Ba chIorate procedures while Ba ion can be detd as
86, accroides gum 11 &’ carbon(fine pdr) 3% described in Refs 2,3 & 5
(Ref 9a,p 229) i)Rus green light: E!a chlorate Faber(Ref 1) describes the following
8.1 & accroides gum 19%(Ref 10a,pp 118 & quantitative tests: moisture, Ba(C103)2,Hz0
195) j)Rus green Iights: Ba chlorate f35 & content; hypochlorites, bromates, acidity,
sheIlac 15%; 13a chIorate 89 & iditol 11% and in.soIuble matter, Ca saIts & Na salts, but he
Ba chIorate .63 Ba nitrate 25 & iditoI 12% advises to make preliminarily the following
(Ref 10a,p 194) k)Ger green signal ~ig~t: qualitative tests for the purpose of detg the
Ba chlorate’8 1.1, S 10.8W char,coal 2.7 & purity of the salt in a general way, in order
calomel 5.4%[Ref 12atp Ger 154) to indicate the method of procedure: a) Flame
Ba chIorate is not used in current US test - by means of a Pt wire moistened with
expl or pyrotechnic compns and there is no US coned HC1, dipped in the powdered salt and
Specification. It was used, however, during heated in the flame of Bunsen burner and
and sometime after WWI and the Specification bichloride test - by adding a few drops of Ag
requirements were, accdg to Faber(Ref l,pp nitrate soln to a soln of Ba chlorate.
163-4), as follows: Color-white, or with Turbidity, in the soln will indicate the presence
on~y very sl yel tinge; odor - none; purity of traces of chloride
as Ba(C103 )2 .H20 99.5%; acidity - none; Kast-Metz(Ref 4) described methods of
insol matter - trace; moisture, m.ax O.270; analysis of green-light pyrotechnic’ compns
bromates, calcd as Br, max 0-01%; Na salrs, contg besides Ba chlorate, the following
calcd as Na20, max 0.25%; K salts, calcd substances: .shellac(or rosin accroides gum),
as K20t max 0.25%; granulation: 100% thru with or without K chlorate, calomel, lacrose,
80-mesh screen and 60% thru 100-mesh. Kast dextrin and powdered carbon or Mg
-Metz(Ref 5b,p 514), gives simiIar require- Re/s: l) Faber, Pyrotechnics 3(1919), 160-64
ments, but in addn: chlorides & sulfates 2)Scott & Furman(1939), 117,127 & 129
-traces and Fe & Ca salts absent 3)Treadwell & Hall, Vols 1 & 2(1942) 4)Kasc
Refs: l) Faber, Pyrotechnics, “3(1919), 151-64 -Metz( 1944), 530-31 5) Vogel, InorgAnalysis
 C 187

(1961), 554 2H20; mw 243.03, wh d.elq monoclinic trysts,

rep-looses Hz O above 100°, further heating
Benzylamine Chlorate, C6H5.CH2.NH2.HCIO~ ; causes decompn; d 2.711; v sol in w; sol in
rnw 191.59, N 7.31%; yel hygr pltlts, mp alc or acet; can be prepd either by saturating
110.5°; sol in w or ale; insol in eth or benz; a hot aq suspension of slaked lime with
was prepd by mixing aq chloric acid with an chlorine, or by electrolysis of CaC12. An
excess of benzylamine. Its expl props were interesting lab method of prepg the pure compd
not inve.stigated is given by Ehret(Ref 5). It is an oxidg
Refs: l)Beil 12, (446) 2)R,L.Datta & J.K. agent which can be used in pyrotechnics when
Choudhury, JACS 38, 1082(1916) an orange-colored light is desired
The Tetra- and Hexa-hydrates have been
reported(Ref 7)
Benzylethylamine Chlorate, C6H~.CH2 .NH.-
Refs: l)Escales, Chloratspr(1910), 13 2).
C2Hs.HC103; . mw 219.67, N 6.37%; CO1 trysts,
Mellor 2(1922), 344 3)Gmelin, Syst Nr 6(1927),
mp 81,5, burns explosively in a flame; sol in
341 4)Ullmann 3(1929), 297 5)W.F.Ehret,
hot w or ale; insol in eth or ben~ was prepd
JACS 54; 3127, 3130(1932) 6)Thorpe 2(1938),
by heating benzylethylamine with a SI excess
214 7)Sidgwick, ChemElems 1 (1950), 257
of aq chloric acid
8)Sax(1957), 425 9) F. A. Warren et al,
Re/s: l)BeiI 12, (448) 2)R.L.Datta & J.K.
“Chlorates and Perchlorates”, NAVORD
Choudhury, JACS 38, 1082(1916)
Rept 7147(V01 1)(1960), 140

Benzylmethylamine Chlorate, C6H5.CH2 .NH,- Chromous Chlorate, Cr(CIO~ )2; its aq soln
CH~.HC109; mw 205.64, N 6.81%; CO1 trysts, was prepd in 1877 by L. Storck & W. de
mp 59.6°$ burns explosively in a flame; sol Coninck by treating chrome alum with barium
in w or ale; insol in eth or benz; was prepd by chlorate; can also be prepd by treating chromic
sulfate with potassium chlorate. The soln is a
heating benzylmethylamine with a SI excess of
aq chloric acid strong oxidg agent. According to Sidgwick
Re/s: l)Beil 12(448) 2)R.L.Datta & J.K. (Ref 3), the solid salt has been made, but it
Choudhury, JACS 38, 1082( 1916) is very unstable
Refs: l)MeIlor 2(1922), 357 2)Ulmann 3
(.1929), 297 3)Sidgwick, ChemElems 2(1950),
Cadmium Chlorate, Cd(C103 )2; mw 279.33, COI
1013
trysts; can be prepd by prolonged heating of
the dihydrate at approx 65° Cobaltous Chlorate, Co(CIO~ )2, very unstable
lh%ydnzte, Cd(C103 )2.2HZO; mw 315.36; CO1 salt; can be prepd by carefully heating the
delq prismatic trysts, mp 80°(dec), d 2.28 at dihydrate. Dihydrate, CO(C103 )2.2H20, pale
18°. very sol in w or ale; S1 sol in acet; can red powd; can be obtd by keeping the
be ~repd by saturating a hot slurry of Cd(OH)z tetrahydrate over P205
with chlorine, or by the action of Ba(CIOs )2 on Tetrahydrate,Co(C103 )2 .4H20; mw 297.92,
CdS04. Both salts are power oxidg agents dk-red trysts; can be obtd by maintaining the
which will explode by heat or shock hexahydrate above 18.6°
Cadmium chlorate reacts with ammonia Hexahydrate, Co(C103 )2 .6H2 O; mw 333.95,
to form Tetramminecadmium( lI) Chlorate, dk-red cubic delq trysts, mp 61°, bp dec at
[ Cd(NH~ )41(C103)2; and Hesammine cadmium 100°, d 1.92; very sol in w or ale; was obtd by
(Ii)’ Chlorate. [Cd(NH3)~ 1(C103 )2, both of Wdchter in 1843 by treating an aq soln of
which are expl metal ammines. See Vol 1, cobaItous sulfate with barium chlorate,
Table A,p A277 filtering the ppt of BaS04, and evapg the
Re/s: l)A.Meusser, Ber 35, 1420(1902) 2) filtrate to dryness over H2S04 below 18.5°
Mellor 2(1922), 350 3)Gmelin, SystNr 6(1927), When treated with ammonia, cobalt
341 4)CondChemDict( 1950), 125 5)Sidgwick, chlorates form the following ammines which
ChemElems 1(1950), 277 6)Sax(1957), 418 are expl: Tetramminecobalt(III) Chlorate,
[CO(NH,)41 (C10,)2; Aquopentamminecobalt(lll)
Calcium Chlorate, Ca(C103 )Z; mw 207.00, wh Chlorate Monobydrate, [CO(NH3 )5. H20].-
delq trysts; can be obtd by heating the (C103 )2 .H20; and Hexamminecobalt(lIl)
dihydrate above 76°. Dihydrate, Ca(CIO~ )2.- Chlorate Morzo.hydrate. [CO(NHS)61 (CIO, )3 .-
 C 188

H20(See VOI 1; Table B,p A27f$ Table C,p conract with coned H2S04; sol in w or aIc;
A279; and Table D,p A280) was prepd by double decompn of dimethyl-
Re/s: l)Mellor 2(1922), 360 2)Ullmann 3 phenylbenzyiammonium bromide & AgC103
(1929), 298 3)Sidgwick, ChemE~ems 2(1950)> and evapn of soln over H2S04. It slowly decomp
1383 4)Sax(1957), 494 5)Gmelin, SYSt Nr to a gray mass when left at RT for several
58(1961), 581 days
Refs: l)BeiI 12,(450) 2) R. L. Datta & J.K.
Cupric Chlorate, Cu(C103)2; the anhydrGus
Choudhury, JACS 38, 1085(1916)
salt has not been prepd. Hexabydrate,
CU(C103 )2.6H O; mw 338.55; grn cubic delq Ethylbenzylamine Chlorate. See Benzyl-
J ethylamine Chlorate, above
trysts, mp 65 , bp dec 100°; v SOl in W; SO1
in alc or acet; was prepd in soln by L.N. Ethylenediamine Dichlorate, H2N.CH2.CHz.-
VauqueIin, in 1815, by dissolving copper NH2.2HC103; mw 229.03, N 12.23.%; CO1 flat
hydroxide or carbonate in aq chloric acid. crysts(from w or ale), mp dec at 150°, burns
In 1843 A.WZchter prepd the solid salt by with a flash in contact with a flame; SOI in w
evapg, in vacuum, the filtrate obrd by mixing or ale; was prepd by neutralizing an ethylene-
aq solns Of Ba(C~O 3)2 & CUS040 Some diamine soln with chloric acid, and evapg the
investigators(Ref I) have claimed that the resulting soln on a w bath to crystn
hexahydrate is really the tetrahydrate This compd explodes violently, when
A basic salt of compn CU(C103 )2 .3 Cu- dry, on heating or shock. It has been proposed
(CX-1)2 is also known(Ref 1) for use, either alone or in mixts with MF, in
When copper chlorate is heated with primers & blasting caps(Ref 2)
ammonia, the fol~owing ammino-compds, Re~s: l)Beil 4, (399) 2) A. St3hler, GerP
which are expl, are formed. Tetrummine- 290999(1915) & CA 11, 1549(1917) 3)R.L.
coppe~~[) Chlorate, [CU(NJ-J3 )4] (C]03)2; Datta & J. K. Choudhury, JACS 38, 1083(1916)
and tfexamminecoppe~ ii) Chlorate, Guanidine Chlorate, H, N. C(:NH).NH,.HCIC),;
[CU(NH3 )6] (C10~)2 (See VO1 1, Table E,p mw 143.54, N 29.27; wh trysts, mp dec
A281). Copper chlorate primary ammine complexes 148°, defgr on hearing in a flame or in
of the general formula CU(C1O ~ )2 NH2 X(where contact wirh coned HeS04; was prepd by
X =CH3, C2 H5, C3H7 or C6H5) were prepd by double decompn of guanidine sulfate & .Ba-
Amiel(Ref 3) by saturating a coned soln of (Clo, )2
CU(C103 )2 with the corresponding ammine. Refs: I)BeiI 3,(40) 2).R.L.Datt.a & J.K.
The resulting complexes are dk-blue tryst Choudhury, JACS 38, 1805( 1916)
expl compds, some of which are unstable Hydrazine Chlorate, H2N.NH2.HC103; mw
even at .RT 116.66, N 24.20%; wh hygr trysts, mp 80°,
Re/s: l)Mellor 2(1922), 342 2)Ullmann 3 explodes when heated above its mp; v sol in
(1929), 298 3)J.Amiel, CR 199, 51-3(1934)& w, v SI SOI in ale; ins.ol in eth, benz or chlf;
CA 28, 5361(1934) 4)Sidgwick, ChemElems its alc SOI is unstable. It was prepd by
1(1950), 155 5)Sax(1957), 516 SaIvadori(Ref 1) by neutralizing a dil soln of
Diethylphenylbenzylammonium Chlorate, chl--ic acid with a dil soln of hydrazine
N [ (C2H5)2C6H~.CH2 CGHe] .C103; mw hydrate, followed by evapg in vacuo over
323.81, N 4.33%; trysts, mp 77°, bp dec H2S04
>125° with effervescence; sol in w or ~lc; This compd explodes violently by
was prepd by double decompn of AgC103 & percussion. Its expl power, according CO
diethylphenylbenzy lammonium chloride. Escales(Ref 2), is considerably greater than
that of MF L
When left in air for long periods, this compd
patiaIly decomposes; and it burns with a Refs: l)R.Salvadori, Gazz 37 II, 32(1907) &
f~ash in contact with a flame JCS 92, 759(1907) 2)EscaJes, Chioratspr
Refs: l)Beil 12,(451) 2)R.L.Datta & J.K. ( 1910), 198 3)ADL, PuteExplsCompds, Part
Choudhury, JACS 38, 1085(1916) 1(1947), 72

Dimethylphenylbenzylammonium Chlorate, Lead Chlorate(Normal), Pb(C103 )2; mw

N [(CH3 )2 C6H5.CH2C6H5 )1C103; mw 374.12, wh hygr trysts, mp dec, d 3.89; can
295.76, N 4.74%; wh hygr trysts, mp dec at be obtd by prolonged heating of rhe mono-
137°; explodes when heated rapidly or in hydrate above 110°. Monohydrate, Pb(C108 )2.-

1
 C 189

H20, mw 392.14; wh monoclinic delq trysts, resulting filtrate to obt LiC103

rnp(looses H20 above 1100), bp(dec above According to Kirk & Othmer(Ref 4),
190° when heated slowly; explodes at 235° L iCIO~ has a limited use in pyrotechnics
when heated .rapidly); s~l in w, nearly insol The prepn of L itbiumtetrammirze Chlorate
in ale. It was prepd in 1843 by W%chter by is reported(Ref 1)
neutralizing a hot soln of chloric acid with Re~s: l)M.ellor 2(1922), 326-29 2)Gmelin,
lead oxide(PbO). W.K.Lewis prepd the salt SystNr 6(1927), 341 3)Ullmann 3(1929), 298
by evapg to dryness equiv amts of PbO & 4)Kirk & Othmer 3(1949), 715 5)Sax(1957), 831
HC103, dissolving the residue in a small amt 6) F. A.Warren et al, C*Chlorates and Perchlor-
of HC103 and addg abs alc which pptd the ates”, NAVORD Rept 7147(VOl 2)( 196°)~
monohydrate(Ref 2) 140-1
Marin(Ref 1) observed that by dissolving Pb Magnesium Chlorate, Mg(C103)2; mw 191.23.
chlorate in hot glycerin, a deposit of wh The anhyd salt has not been prepd. Dibydrate,
trysts formed, after cooling the soln, which Mg(C103 )2. 2H20, forms on drying the tetra- or
when separated & washed with alc constituted hexa-hydrate at 65°. Tetrahydrate, Mg(C103 )2.-
a very powerful detonating substance. It 4H30, forms on drying the hexahydrate at
exploded violently when subjected to either 35 l Hexabydrate, Mg(C103)2 .6~0, mw
heat or shock and was proposed for use in 299.33, wh delq trysts, mp 35ff, dec at 120°, d
various primary compns for detonators, and 1.80 at 25°; very sol in w, In 1.844, A. Wachter
in pyrotechnics prepd the hexahydrate by treating Ba(C103)2 with
Re/s: See below under Lead Chlorate(Basic) the hexahydrate by treating Ba(C103 )2 with
Lead Chlorate(Basic), Pb(C103)2.Pb(OH)2; MgS04 in aq soln, filtering the pptd BaS04
mw 615.35, wh solid; can be prepd by treating and evapg the filtrate over coned H2S04
2 mols of lead oxide with 2 mols of hot (Refs 2,3 & 4). According to Sidgwick(Ref 5),
coned chloric acid. There are also Dibasic this compd is formed when chlorine is passed
and Tribasic salts into cold w contg magnesium oxide in
Marin(Ref 1) reacted basic lead chlorates suspension
with glycerin, tannin or coned solns of Magnesium chlorate was proposed by
carbohydrates to obt various amor complexes. von Weldon as a starting material in the
When di- or tri-basic salts were used, the prepn of other chlorates, when it is desired
resulting complexes were nearly insol in w. to obt them in the pure state(Refs 2,3 & 4)
The most powerful & brisant of these expls Re/.s: l)K.A,Hofmann et al, Ber 47, 1993
were those prepd brom Pb chlorates & glycerin. (1914) 2)Mellor 2(1.922), 349 3)Grnelin,
These complexes exploded violently by heat SystNr 6( 1927), 341 4)Ullmann 3(1929), 298
or shock and were proposed for use in primer 5)Sidgwick, ChemElems 1 (1950), 240 6)Sax
& initiating mixts (1957), 841 7)F.A..Warren et al, “Chlorates
Refs: l)A-J.Marin, Frp 478351(1915) & CA and Perchlorates”, NAVORD Rept 7147(Vol
10, 2300(1916); USP 1206456(1916) & CA 1)(1960), 141
11, 211(1917) 2)Mellor 2(1922), 356 3)Gmelin, Manganous Chlorate, Mn(C10~)2; mw 221.86.
Syst Nr 6(1927), 339 4)Ullmann 3(1929), 297 In 1843 A. W?3chter(Ref 1) prepd a nearly
5)Siglgwick, ChemElems 1 (1950), 625 6)Sax colorless soln of manganous chlorate by
(1957), 817 7)Ellern, Pyrotechnics(1961), 56 treating Ba(C103)2 with manganous sulfate
Lithium Chlorate, LiC103 ;-row 90.04; CO1 and filtering the ppt of BaS04. Evapn of the
delq rhmb ndls, mp 124-29°, dec at 270°; can be filtrate was successful up to a certain concn,
prepd by heating its hydrate to 90°. Sesqui- then decompn took place and the soln turned
bya%ate, LiC109.~H20; mw 99.4o; CO1 tetragonal red. Jahnsen(Ref 2) obtd a yel-brn ppt of
Manganous-amino-chlorate by treating a cold
crysrs, mp 65°, bp(looses w at 900); very
soln of Mn(C109 )2 with ammonia. This product
sol in w(314g per 100g w) or in ale. It can
was unstable and rapidly darkened by oxid~
be prepd by one of the following methods: Re/s: l)A.W~chter, JPraktChem 30, 321(1843)
a)electrolysis of lithium chloride ~oln
2)A.Jahnsen, “fiber die Ammoniakate einige
b)interaction of Ba(CIO~ )2 & Li2S04 solns Schwermetallchlorate, -bromate, und -iodate”,
and c)by mixing aq solns of LiCl & NaC103, Dissertation, Ziirich(1915) 3)Mellor 2(1922),
separating the pptd NaCl, and concg the
359
 C 190

Mercuric Chlorate, Hg(C103)2; mw 367.52, Piperazine Chlorate (Diethy lenediamine Chlorate),

CO1 delq needle-like trysts, mp dec, d ,CH2 .CH
*
4.998; dec in contact with w; coned H2S04 HN. , NH.2HC103; mw 255.08, N
produces flashes of light. According to Mellor ‘CHz.Cfi2
(Ref 1), the basic salt, Hg(C103 )OH was 10.98%; wh shiny tryst plates, mp dec
first prepd in 181S by L.N. Vauquelin by the 98-100°, defgr in a flame; was prepd by
action of chloric acid on H@ and subsequent double decompn of silver chlorate &
evapn of the soln piperazine
.- hydrochloride
R efs: See below under Mercurous Chlorate Re/s: l)Beil 23,(4) 2)R.L.Datta & J.K.
Mercurous Chlorate, HgC103; mw 284.07, wh Choudhury, J ACS 38, 1083(1916)
rhmb trysts, mp detonates ca 250°, d 6.40~ Potossium Chlorate, KC103; mw 122.55;
sol in w, alc or acet ac. This salt was first CO1, non-hygr monoclinic trysts, mp 368-70°,
prepd in 1815 by L.N.Vauquelin, in 1843 by bp dec ca 400°, giving off oxygen; d 2.32,
A. W;chter, and in 1895 by I. Traube all by the Qf -93.5 kcal/mol; Heat Capacity 23.96
action of chloric acid on Hg20(Ref 1). It can cal/deg/mol at 298° K; sol in w, alkalies or
also be prepd by the action of K or Na chlorate aq KC1; S1 sol in glycerol or ethyleneglycol;
on a soln of mercurous nitrate nearly insol in abs alc or abs acet, Potassium
It is an oxidg agent which explodes when chlorate is S1 to moderately poisonous; the
heated to decompn, but in admixtue with com- principal toxic effects are the production of
bustible materials, it explodes more violently methemoglobin and the destruction of red
than when alone blood corpuscles. The probable lethal dose
Refs: l)MeIlor 2(1922), 351 2)Sax(1957), is 50-500 mg/kg or betw one teaspoonful and
857 & 865-66 one ounce for a 150-lb man
This salt was first isolated by C.L.
Methylbenzylomine Chlorate. See Benzyl-
BerthoHet about 1786, hence the name
methyl amine Chlorate, above
(‘Salt of Berthollet”. Two of the more
Nickel Chlorate, Ni(C109)z; mw 225.60. important methods of prepg KC103 are:
Anhyd salt has not been prepd. Tetrabydrate, a) CbemicaI(lndirect) Method in which a hot
Ni(C103)2.4H20; mw 261.62; is formed by satd soln of KC1 is added, in S1 excess, to
heating the hexahydrate to 39°. Hexahydrate, a hot satd soln of Ca(C103)2; the soln is
Ni(C103 )2 .6HZ O; mw 333.70; dk-red trysts, cooled to 0° and filtered, the ppt is washed
mp(looses w at 390), dec at 80°~ d 2.07; SO1 with w and dried and b) Electrolytic(Direct)
in w. Was obtd by W2chter in 1843 by the Method by electrolysis of KCI in a diaphragm-
double decompn of nickel sulfate & barium Iess cell, using a cathode of steel & anode
chlorate, followed by filtering the BaS04 of graphite(Ref 19)
and evapg the filtrate at RT over H2S04 Potassium chlorate is a very powerful
(Ref 2) oxidg agent and, in admixture with combustible
Ephraim & J ahnsen(Ref 1) prepd blue materials, it forms very powerful expls.
needle-like trysts of Hexamminerzickel( lf) According to Stettbacher(Ref 12), KC103
Chlorate, [Ni(NH3)61 (C10,)2, mp 180°, yields the most expl mixts with reducing
dec explosively at 210°, d 1.52, by treating materials, in comparison with other oxygen
Ni chlorate with ammonia. 5ee Vol 1, Table releasing salts; the most dangerous is
E,p A281 Armstrong’s Mixture co ntg red phosphorus
Re/s: l)F.Ephraim & A. Jahnsen, Ber 48, & KCIOa(See Vol l,p A485-R). P4rez Ara
42(1915) 2)Mellor 2(1922), 360 3) Ullmann (Ref 16) reports that mixts of KC103 & sulfur
3(1929), 299(erroneously lists as anhyd are unstable and are readily exploded by heat
salt) 4) J. Amiel, CR 198, 1033-35(1934) & or impact. The instability of sulfur-KC103
CA 28, 2633-34( 1934)( Reactions of chlorates mixts is discussed in detail by Tanner(Kef
with sulfur, selenium, tellurium & org matter) 24). Mixts of KC103 & sugar are also very
5)Sidgwick, ChemElems 2(1950), 1437 6)Sax expl and may be detonated by flame, heat,
(1957), 934 impact or in contact with coned H2S04
Accg to Marshall(Ref 4, vol 1, 378)
Dupr< showed that heat aIone suffices to
explode KC103 if it is applied with suddeness.

1
 C 191

Under ordinary conditions, KC103(like and provides oxygen required for combustion
NH4N03 ), when not in contact with combustible of other ingredients. It has, however, the
matter, is not a dangerous material. However, disadvantage to corrode firearms, because one
in 1899 a large quantity exploded dining a of the products of its decompn is hot vapor
fire at the United Alkali Co, St Helens, of KC1, which is corrosive
England and did an enormous amt of damage. Following are examples of US military
Other serious explns occurred at Manchester primer and igniter compns contg K chlorate:
in 1908 and at Seaforth in 1910, both in a)Primer Mix, US Army .Starzdard K chlorate
England. Consequently, KC103 should be 33.4?2.0, Sb sulfide 33.3k2.0, LA 28.3 &
stored in a fire-proof bldg away from com- Carborundum 5. O-@5%(Addnl Ref j, Method
bustible materials, and it should be handled No 202 & Addrd Ref k) b)Primer Mix No 70:
with great care K chlorate plus gum 53.Oi 5.0, Pb thiocyanate
Explosive Properties. Kast showed(Ref 7a) 25.0~3.0, Sb sulfide 17.0~2.O & TNT(Grade I)
that when K chlorate is heated in a sealed 5. Ofl.5%(Addnl Ref j, Method No 205 & Addrd
capillary a defgrn accompanied by weak noise Ref 1) c) Primer Mix P-1OO: K chlorate
takes place; when heated on a spatula or 53.0~2..O, Pb thiocyanate 25.0$1’.0, Sb sulfide
dropped on a red-hot iron surface an instant 17.0~1.0, & LA 5. O~I%(Addnl Ref j , Method
decompn with evoln of oxygen takes place. No 206 & Addnl Ref k) (Comp.ar~ with Addnl
It is fairly insensitive to impact(one deton Ref e) d)Igniter Mix /or M31A1 and some
and one defgrn out of 6 tests were obtained other detonator assemblies: K chlorate
with a 20kg wt dropped from the height of 55.0~1.O & Pb thiocyanate 45.0~1.0% .
16cm) and to friction(when tested by rubbing Following are examples of pyrotechnic
in a porcelin mortar). Its thermal stability compns(some of them obsolete) contg K
proved to be very good even when heated to chlorate: a)Rocket red signal compn: K
temps 170-80°. Attempts to ignite it by means chlorate 25, Sr nitrate 66.6 & orange shellac
of BkPdr fuse were unsuccessful and the 8.4%(Ref 5,p 140) b)Red rifle & red V.4ry
tests for power(by Trauzl method), detonation pistol light compn: K chlorate 72.7, Sr
velocity (by Dautriche method) and bris ante carbonate 15.2 & orn shellac 12.l%(Ref 5,pp
(by copper cylinder crusher method) produced 140 & 182) c)Red position light compn: K
no measurable value s(Ref 7a). Accdg to chlorate 37.5, Sr nitrate 50 & orn shellac
Blinov(Ref 13a), K or Na chlorates explode 12.5%(Ref 5,pp 32, 140 & 184) d)Green
from a strong impact, if they ate at temps position light compn(See under Barium
above rep’s Chlorate, Uses) e) Smoke torch blob compn:
Some expl props of mixts of K chlorate K chlorate 88.9, red gum(gum Kauri) 7.4 &
with charcoal~ woodmeal or Al power are charcoal(fine) 3.7%(Ref 5 ,p 140) f )Yellow star
given in Ref 7a compn: K chlorate 70, Na bicarbonate 15 &
Uses. Berthollet tried to use KC1O ~ in BkPdr shellac 15%(Ref 20a,p 206) g)Red star compn:
as a replacement for saltpeter, but the results K chlorate 55, Sr carbonate 21, lactose 15,
were disastrous(Ref 15). It took more than shellac 7 & carbon black 2%(Ref 20a,p 207)
100yrs to learn how to prep KC103 expls in h)Red signal compn: K chlorate 76, Sr oxalate
such a manner as to be comparatively safe 8, shellac 7 & tar 9%(Ref 20,p 207) i)Blue
to handle. Large amts of KC103 have been star compn: K chlorate 70, CUS04 ,4NH3.HZ0
used in HE’s ,(such as Chedditest Koh- 15 & shellac 15%(Ref 20a,p 2 13) j)vkdet
Iensprengstoffe, etc) in primer & igniter mixts star cornpn: K chlorate 58.5, Sr chlorate 14.5,
(in combination with MF, LA, Sb sulfide, Pb Cu carbonate 10, sulfur 10 & shellac 7%(Ref
thiocyanate wih or w/o abrasives), in matches, 20,p 215) k)Colored smokes compns: K
toy caps, pull-wire igniters, electric squibs~ chlorate 28, coloring substances 36, lactose
RR torpedoes, smokes, flares & signal lights 28, sulfur 4 & Amm chloride 4%(Ref 20a,p 234)
(See also Refs l,4,5,7,12,13a,14,15,16,17,18, I)Various colored smoke compns. See Ref
20a,21,22a,24a,26 & Addnl Refs). Some Ger 20a,pp 235-38 m)Russian red light signal
primer compns of WWII are listed in Ref 23a,p compn: K chlorate 57, Sr carbonate 25 &
Ger 136 shellac 18%(Ref 22a,pp 73 & 84) n)Rus red
When used in primer and igniter compns, smoke compn : K chlorate 35, rhodamine 40
KC103 increases their sensitivities to frictlcn & lactose 25%(Ref 22a,p 73) O)RUS photo
 C 192

mixt: K chlorate 63 & Mg 37%(Ref 22a,p 84) Following are chemical requirements:
p)Rus black smoke compns: K chlorate 45, Grade A Grade B
naphthalene 40 & charcoal 1570 and K chlorate Moisture, max, % 0.05 0.05
55 & anthracene 45%(Ref 22a,pp 241-2) q) KC103, rein, % 99.5 99s
Russ blue smoke compn: K chlorate 35, H20-insols, max, % 0.02 0.10
synthetic indigo 40 & lactose 25 %(Ref 22a,p pH value 5-8 5-8
242) r)Rus yellow smoke compn: K chlorate Hypochlorites None None
34.6, aminoazobenzene 40 & lactose 25.4% Chlorites None None
(Ref 22a,p 251) S)RUS blue smoke compn: Chlorides(as KCI), 0.10 0.10
K chlorate 35, methylene blue 60 & lactose 5% max, %
(Ref 22a,p 252) t)Ger pyrotechnic compns. Bromates(as KBr03 ), 0.02 0.10
See Ref 23a,p Ger 154 max$ %
Ellern(Ref 26,pp 270-80), lists numerous Heavy metals None None
compns contg K chlorate of which the following Alk-earths None None
are exampIes: A) Military or special safety Na-salts(as NaC103), 0.09 0.09
match: a)K chlorate 88, charcoal 10 & max, 70
dextrin 2% b)K chlorate 50, Sb sulfide 30 & Grit None None
dextrin 20% and c)K chlorate 60, Sb sulfide
(black) 6, ground glass 22.5 & gum arabic 11.5% These two grades are subdivided into
B)SAW(strike-any where) match: K chlorate 32, six classes accdg to granulation(See Table
P4S3 10, powdered glass & other filler 33, II in Ref 28)
ZnO 6, rosin 4, animal glue 11 & extender 4% Tests are described under Potassium
C) Older types, percussion primers: a)K Chlorate, Analytical Procedures
ct,lorate 53, Sb sulfide 17, Pb thiocyanate Re/s: l)Escales, Chloratspr(1910), 13-41,
25 & TNT 5%; it was moistened with gum soln 52-61 & 143-49 2)S.Smith, PrChSoc 26, 124
& pressed in primer caps while wet and b)K ( 1910) & CA 4, 2206( 1910)(Action of sulfuric
chlorate 41.5, Sb sulfide 9.5, CUCNS 4.7 & acid on K chlorate) 3)G.B.Taylor &. W.C.
ground glass 44. 3% D) Electric primer compns: Cope, ChemMetEngrg 15, 141-43(1916)
a)K chlorate 60, DADNPh 20, charcoal 15 & (Hygroscopicity of K chlorate 4)Marshall 1
NS 5%(suitable for ignition rather than for (1917), 377; 2(1917), 688 & 759 and 3(1932),
detonation) and b)K chlorate 55 & Pb 111-12 5) Faber, Pyrotechnics 3(1919), 127-50
thiocyanate 45% E) Colored smokes: K chlorate 6)Mellor 2( 1922), 297 & 326 7)C.A.Taylor
22-33, dye 30-50, Na or K bicarbonate 3-10, & W. H.Rinkenbach, ‘tExplosives”, USBur-
confectioner’s sugar or lactose 20-35, kerosene MinesBull 219, Washington, DC(1923), 32-6
or paraffin oil 2-4, kieselguhr O-.4 & red iron 7a)H.Kast, SS 22, 58-61 & 78-9( 1927)(Some
oxide O-3% F) ’Plastic Bonded’ colored expl props of K chlorate) 8)Gmelin, Syst Nr
smoke: K chIorate 23, dye 51, sugar 18 & K 6(1927), 337 9)Ullmann 3(1929), 297-98
bicarbonate 8%; combined with 2.2 parts of 10)W. A. Noyes, Jr & W. E. Vaughan, ChemRevs
polyvinyl acetate plasticized by dichloro- 7, 240-42(1930), (Thermal decompn of K
methane and dried by evapn G )CCap’ mixtures: chlorate) 1 l) K. A. Hofmann & P. H. Marin,
a)K chlorate 67, red P 27, S 3 & pptd Ca SitzberPreusAkadWis senschPhysik-MathemKlasse
carbonate 3%, bound with unspecified amt 1933, 450( Thermal decompn of K chlorate alone
of ‘gum water’ and b)K chlorate 61, red P 4, or in mixt.s with K nitrate) 12)Stettbacher 1
black Sb sulfide 21,pptd Ca carbonate 2 & (1933), 310-11 13)M.Meyer, JChemEduc 17,
animal glue 12% H)Railroad torpedo: K 494( 1940) (Thermal decompn of K chlorate in
chlorate 40, S 16, sand(60 mesh) 37, binder 5 presence of chromic oxide & K bichromate)
& neutralizer 2% I)Whistling compns: K 13a) LF.Blinov, “Chlorate and Perchlorate
chlorate 73-77, gallic acid 24-19 & red gum Explosives’’(in Rus), Oborongiz, Moscow
3-4%(Ref 26,pp 270-80) (1941), 40-45 14) A. Alberto & M. R. LiberalIi,
Accdg to Ref 28, there are two grades of AnaisAcadBrasilCienc 15, 373-75(1943) &
K chlorate for use in US ammunition: a)Grade CA 38, 2491( 194 I)(Small amt of KC103 in TNT
A is intended to be used as an ingredient of greatly increases its sensitivity to shock)
primer mixtures and b)Grade B to be used as 15)Davis(1943), 64-7,70,72,84-8,104,117,119,
an ingredient of pyrotechnic mixts 123,354-61 & 453-6 16)P~rez Ara(1945),
 C 193

203-5 17)Anon, OpNav 30-3M(1945), 28 in some foreign primers and detonators) e)K.S.
(Jap expls Ennayaku & Entoyaku using Warren, PATR 1569(1945)(Development Of the
KC103) 18)Weingart, Pyrotechnics(194i’), mixt: K chlorate 50, Pb thiocyanate 35 & Al
6.3-1,63-4,66-7,72,127,132-6,141-2,146-7,171 & 15%, which is more suitable for some primers
194-7 19)Kirk & Othmer 3(1949), 708-16 than previously used PA-1OO Primer Mix)(See
& 11 (1953), 323 20)CondCher@ict( 1950), under Potassium Chlorate, Uses) e, )Compagnie
538 20a)Izzo, Pirotecnia(1950), 204-17, de produits chimiques et ~lectrom~tallwgiques
225-8 & 234-8 (Use; of K chlorate in Alais, Eroges & Camargue, FrP 969032(1950)
pyrotechnics) 21 EtatFran~ais, FrP 971644 & CA 46, 6388( 1952) (Match-head compn
(1951 )& CA 46, 9311( 1952)(Expl powders contg specially prepd KC103 ) f) B. A. Rausch,
contg combustible materials & KC103) 22) PATR 2120( 1955 )(Development of igniter
S. Yamamoto & T. Asaba, JIndExplSocJapan compn: KCIO~ 39.6, Pb(SCN)2 32.4, charcoal
13, 235-41(1952) & CA 49, 6761( 1955) (Effects 18 & lacquer binder 10% to replace the flash
of inert substances on thermal decompn of compn: KC103 60, DADNPh 202 carbon 15 &
KC103 ) 22a)Shidlovskii( 1954), 21-2, 25,27, NS 5% for use in electric initiating elements)
67,73,84-5,91,93,118,187,191,195-6,242, g) A. M. Anzolone et al, PATR 2179(1955)(C)
247-8,250-2 & 254( Prop,s of KC103 and its h)B.A.Rausch, PATR 2220(1955)(U)
uses inpyrotechnic compns) 23)Sax( 1.957), (Evaluation of several styphnate type primer
1038 23a)PATR 2510( 1958),pp Ger 136 compns as possible substitutes for std
(Primer compns)&Ger 154( Pyrotechnic chlorate-based compns in percussion Primers).
compns) 24)H.G.Tanner, JChemEduc 36, i) A. M, Anzalone, PATR 2227(1955)(C) j)
58-9(1959) 24a)F .A.Warren et al, “Chlorates A. R. Lusardi, “Laboratory Manual”, Expls &
and Perchlorates”, NAVORD Rept 7147(V01 1) ProplntsLab, PicArsn, Dover, NJ(1962),
(1960), 68-70 & 142; Ibid, Vol 2(1960 )(Conf) Methods 202,203,204,205,296,208 & 209
(not used as a source of info) 25)1.Huhtanen, k)US Military Specification MIL-D-2493
Explosivst 1960, 189-94 (Some thermochemical (superseding PA-PD-124) l)US Military Spec
data for KC103 and its mixts with combustible MIL-P-20U9A(superseding MIL-E-20449)
materials for use in Cheddite-type expl S) 26) Potassium Chlorater Analytical Procedures.
Ellern, pyrotechnics(1961), 51,66,97,99,100, Chlorate ion can be detected and detd as
111,126,128,148,171,188,208,254 & 270-80 described under Chlorates, Analytical
(Uses of KC1O ~ in various pyrotechnic Procedures. Potassium ion may be detected
compns) 27)Anon, “Pyrotechnics Handbook”, by dipping a Pt wire moistened with coned
Vol 3, Chapter XVI, Ingredients, Part II, HCl into powdered sample and heating it in
McGraw-Hill Technical Writing Service, NY the non-luminous flame of a Bunsen burner.
(1962) 28)US Military Specification MIL-P If the collor of flame .is. violet, the salt is
- 105 A(Potassium chlorate for use in fairly pure(Ref l,p 141 & Ref 3,p 862). K
ammunition) can be identified by pptg it as K2NaCo(N02)~,
Addnl Refs: a)W.R.Tomlinson et al, pATR as well as by potassium salts of chloro-
1316( 1944)( Percussion- and stab-sensitive platinate, perchloratei acid tartrate, picrate,
compns KCIO~-Sb2S3-MF-abrasive used dixing silicofluoride, etc(Ref 3,p 862). Various
WWII in some foreign cartridges as first chge. quantitative methods for detn of K ion are
Mixts KC103-Sb2S3-abrasive with occasional given in Refs 3,4,4a & 8
addn of carbon or MF used as percussion Analyses of commercial K chlorates are
chges in some foreign fuze primers) b)K.S. given in Refs 1,2,7 & 10. Determinations of
Warren, PATR 1411( 1944)(Development of K chlorate in mixts with other ingredients are
primer mixt for M-5 Chemical Mine Fuze. It given in Refs 1,3,5,7,9,11,12,13 and under
consisted of K chlorate & Pb thiocyanate and Cheddites, Analytical Procedures
was similar to std igniting mixt for M-31 Following are US Military Specification
detonator) c)K.S.Warren, PATR 1448(1944) tests:
(Mixts of K chlorate with basic Pb 4t6-dinitro- A)Moisture. Heat a 10g, accurately weighed
resorcinate were found to be not sufficiently sample together with a tared container, for
sensitive to initiation in order to serve as 5hrs at 100°, cool in a desiccator and weigh,
possible constituents of primer” compns ) d)K.S. Save the sample for next opn
Warren, PATR 1450( 1944) (Uses of K chlorate B)K chlorate content. Weigh ac :urately a
 C 194

0. 15g sample of dry material(saved from opn where V = ml of Aq chloride required for
A), dissolve in 100ml of distdw contained in sample soln; v = ml required for blank;
a 500ml Erlen fl and add exactly 50ml of an W= wt of sample in. 100ml aliquot, calcd on
8% soln of (NH4 )2 Fe(S04)2 .6HzO(Mohr’s salt). the dried sample
Close the flask with Bunsen valve and heat H) Brornates. Pipette a 200ml aliquot(from
the soln to boiling. Two reins after steam soln prepd in opn D) into a 500ml glass
ceases to emit from the valve, cool the flask stoppered iodine flask, add 5ml. of 1:9 HCI-W
rapidly to RT and remove the valve. Add 10ml soln and 5ml of freshly prepd 10% KI soln
of Zimmermann-Reinhardt reagent(prepd by followed by 5ml of starch indicator. Stopper
cautiously adding 12.5ml of coned sulfuric acid the flask, shake it and set in a dark place for
& 12.5ml of phosphoric acid to 7g of MnS04.- lhr. Titrate the contents with 0.02N Na
4H20 dissolved in 50ml of w, and diluting the thiosulfate soln until the blue color disappears
mixt to 100ml), shake and titrate the excess Run concurrently a blank using 200ml of distd
of Mohr’s salt with std O.lN soln of K per- w and the same reagents as above
manganate. Concurrently run the blank value %KBrOa= [ 2.783 (V-V)N] /W,
for exactly 50mI of 8% Mohr’s salt where V. ml Na thiosufate used for sample
%KC103= [ 2.043(V-V)N] /w, titration; v = ml for blank; N= normality of Na
where V = ml of KMn04 required for blank, thiosulfate soln; and W= wt of sample in 200ml
v = ml required for sample soln; N = normality aliquot calcd on the dried sample
of KMn04; and W= wt of dry sample I)Heavy metals. Acidify 25ml aliquot from
C) Water-insoluble material. Dissolve ca 50g opn D soln with 0. lN HC1 soln and bubble
of original sample in ca 650ml of warm distd H2S gas thru the soln for ca 30 sees. No pptn
w filter the soln thru a tared filtering crucible or coloration should result
and wash the residue with 5 portions of hot W. J)Alkaline-earth metals. Alkalize 25ml aliquot
Dry the crucible for lhr at 105°, COOI it in a from opn D with lml of 10% Amm hydroxide
desiccator and weigh. Save the filtrate and soln, add 5ml of 10% Amm oxalate soln and
residue for subsequent opns heat the mixt nearly to boiling. No ppt should
D)pfl value. Cool the. filtrate from opn C to be formed on cooling
RT, transfer it to a 1000ml volumetric flask K)Sodium salts, are detd gravimetrically by
and dilute to the mark. Remove part of soln means of magnesium uranyl acetate reagent,
and det its pH by means of a standardized using a 20g sample. As this, rather tedious
pH meter method, is essentially the same as described
E)Hypochlorites. Dip a strip of KI-starch in the literature(See Ref 3,pp 879-81 and Ref
paper into the soln used for pH test and if 8,pp 558-60), no description is given here
the paper does not turn immediately blue, L) Grit. Place the water-insol residue of opn
hypochlorites are absent. Save the soln for C on a small smooth glass plate and rub with
opn F. If the paper turns blue(which indicates a smooth steel spatula or blade. Any rough
the presence of hypochlorites ), the test for particles which behave in the manner similar
chlorites should be disregarded to sand, when it is ground betw glass and
F) Cblorites. If hypochlorites are absent add steel, should be considered as grit
to soln of opn E ca 2ml of O. lN sulfuric acid M) Granulation. For classes 1,2,3,4 & 5 a
and dip the KI-starch paper. If it does not 100g sample is shaken on appropriate set
turn immediately blue, chlorites are absent of sieves 10mins by hand or 5mins by means
G) Chlorides. Pipette out 100ml aliquot(of of a mechanical shaker geared to produce
soln prepd in opn D) into a white porcelain 300~15 gyrations and 150~10 taps of the striker
dish, add lml of 5% K chromate soln and per min. The portions retained or passed by
titrate with the soln (contg exactly 4.791g the various sieves should be weighed and the
of purq dry Ag nitrate per 1000ml of aq soln) results calcd to the percentage basis. For
to the first perceptible color change. Run class 6* .a 10g sample is placed on a dry
concurrently a blank by titrating under the tared, 3.” diam No 325 US Std sieve, and
same conditions of lighting and background, washed with a steady gentle stream of
100ml of distd w contg lml of the same K isopropanol(previously saturated with K
chromate soln to the same color change chlorate at 25~5° ) from a wash bottle, breaking
%KC1= [o.2i(v-v)l /w, UP any lumps by means of a glass rod. During
 C 195

the washing the sieve should be shaken the contact surface betw the two liquids
gently and occasionally the bottom of the g) Cbl~rides. Acidify slightly with dil nitric
screen tapped. ,Washing should be continued acid 10rnl of filtrate from opn d and add
until no more sample passes thru the sieve; lml of 10% Ag nitrate soln, If turbidity is
then the sieve is dried on a steam bath and in obtained within 5mins, chlorides are present.
an oven at 100-105° for 15mins, cooled in a Compare the turbidity with those obtained
desiccator and weighed. No more than 5% of with solns contg known amts of chlorides
sample should be retained on the sieve (Ref 7)
Tests conducted at the Bofors labs(Ref For large amts of chlorides, detn is
7) include the following: made by titrating a neutral soln of sample
a)Appeammzce. White and free from mechanical with O. IN Ag nitrate soln using ca 10 drops
impurities of 107o K chromate indicator, to the first
b)KCIO~ content. Dissolve an accurately reddish coloration(For details see Ref 7,p
weighed O. 5g sample in 200ml distd w con- 103)
tained in a 400ml tall beaker, add & dissolve h)Sulfates. Acidify slightly with dil HC1(l: 1)
5g of Na nitrite(chloride-free) and then 50ml 10ml of filtrate from opn d and add lml of
of O. IN Ag nitrate soln. Cover the beaker with 10% Ba chloride soln. If turbidity is obtained
a watch glass and boil gently in a hood(while within 15mins, sulfates are present. Compare
adding distd w occasionally to maintain the the turbidity with those obtained with solns
original volume), until the evoln of nitrous contg known amts of sulfates(Ref 7,p 103)
fumes ceases. Cool and add 5ml of 10% ferric For large amts of sulfates, detn is made
alum soln(contg 10ml of coned nitric acid per by gravimetric method described in Ref 7,p
liter) as indicator and titrate with O. IN Amm 103
thiocyanate soln. Run concurrently a blank i)ffeavy metals. Acidify 10ml of filtrate from
detn opn d with 0.5ml of 10!Z HCI soln and bubble
%KC103 = [ 12.255 (b-a)nl /w, hydrogen sulfide thru it for lmin. Dark
where b = ml of thiocyanate soln used for coloration or ppt indicates heavy metals
sample; a = ml used for blank; n = normality of j)Alkaline-earths. Alkalize 10ml of filtrate
thiocyanate soln; and w= wt of sample from opn d with 0.5ml ammonia, add 2ml of
c)Bromate~. The method is essentially the 10% Amm oxalate soln, heat to nearly boiling
same as the US spec method, described here and then cool. Ppt or turbidity indicates the
as H, except that a 2g sample is used and presence of alkaline-earths
Na thiosulfate soln is O.OIN. Starch indicator k)A mmonium salts. Warm ~,, a test tube a lg
is a 1% aq soln sample with 10ml of 10% NaOH soln and if
d) Water-insoluble matter. The method is ammonia is evolved(as indicated by odor or
essentially the same as the US spec. method by moistened litmus paper held in the
described here as C, except that a 10g opening of the test tube), the sample contains
sample dissolved in 200ml distd w is used. an Amm salt
The filtering crucible is of medium porosity, l)Sodium salts. Heat a clean Pt wire over a
such as Jena IG3 or Pyrex M. Save the filtrate Bunsen flame until no yel flame is visible,
e)Percblorates. Det them qualitatively by cool, plunge into a satd soln of sample and hea
adding to 10ml of filtrate from previous opn, as above. Yel coloration of flame indicates
0.5ml of 0.3% aq soln of methylene blue. In the presence of appreciable amt of Na salt.
the presence of perchlorates, a violet ppt If only traces are present a very pale yel
with green fluorescence is formed color is observed besides the characteristic
/)Nitrates. Mix in a test tube a few mls of violet color of K salt
opn d filtrate with lml dil sulfuric acid and A more. precise “flame spectrophotometric
some cold satd ferrous sulfate soln. While method” is given in Ref 6
keeping the test tube inclined, let a few mls m)Reactiorz. Dissolve a 10g sample in 200ml
of coned sulfuric acid run slowly (from a of hot distd w, cool, filter thru a coarse
pipette) down along the inner side of the paper and wash the filter with 50ml distd w.
tube, so that the acid does not mix with the Divide the filtrate into two parts and add to
aq soln but forms a layer under it. If nitrates one part a few drops of methyl red indicator
are present, a dark brown ring will appear at and to another part a few drops of phenol-
 phthalein soln. If the 1st part turns red the disconnect the crucible from adapter in the
soln is acid and if the 2nd part turns pink , neck of suction flask, and wipe the bottom of
the soln is alkaline crucible with tissue paper. Repeat the above
n) Moisture is detd by heating a 5-10g sample opns, first with another 3.Oml portion of soln
at 100” for 2hrs or by Karl Fischer method No 1, then with two 2.Oml, and two l.Oml
(Ref 7,p 15) portions making a total of 12.Oml of soln No 1.
o) Grarzulation is detd as described in Ref 7,p Remove the crucible, discard the filtrate and
23. US Std sieves or Tyler sieves can be wash with distd w the outside of crucible, the
used adapter and suction flask. These opns are
Bofors AB also describes(Ref 7,p 150), supposed to remove, completely K chlorate,
the following calorimetric method for detn of leaving other ingredients of primer mix intact.
chlorates in perchlorates: Mix a2g sample In order to verify the completeness of washing,
with 2ml of aniline reagent(3.6g of aniline swirl the crucible with another lml portion of
dissolved in IOOml of 1:1 HCI soln) and 0.5ml sohr No 1 and transfer the liq by suction to a
distd w. If a blue or green coloration appears test tube. Mix its contents with lml distd w,
within 30mins, chlorates are present. Det the incline the tube at an angle of ca 45° and add
contents as KC103, by comparing the color slowly from a dropper ca O. 5ml of diphenyl-
of sohr with these obtained with solns of amine reagent( lg of DPhA dissolved in 100ml
pure KC103 of known contents of coned sulfuric acid) in such a manner that
Determinations of K chlorate in expls are it runs along the inner side of the tube
similar to those described under Cheddites, without mixing with soln No 1 but forms a
Analytical Procedures layer under it. If an appreciable amt of
Determinations of K chlorate in primer- and chlorate ion is present, a distinct blue ring
igniter- compns are described in Refs 5,9,11, will be visible at the junction of the two
12 & 13 layers. On shaking the tube, the ring disappears,
Following procedure was developed in but the contents assumes a blue coloration,
1950 at PicArsn and isincorporatedin Spec which lasts several seconds depending on the
MIL-D-2493(Ref 12,pp 6-7). It is applicable amt of chlorate ion present. If only a trace
to mixes contg K chlorate, Sb sulfide, LA & of chlorate ion is present, the blue ring may
Pb thiocyanate not form, but upon shaking the test tube, a
Prepn o{.wash solns: slight bluish coloration will appear moment-
Soln No 1. Add to ca 800ml of distd w in 1 arily throughout the soln, lasting only a
liter amber glass bottle, ca 40g of K thiocyanate, fraction of a second. If a definite blue ring
insert a rubber stopper and shake until forms, repeat the washings as before using
complete dissolution. Add to this soln l.Og one l.Oml portion of soln No 1, followed by
Pb thiocyanate, lg of Sb sulfide and lg of LA; O.5ml portion. Usually nor more than a total of
restopper the bottle, shake vigorously for ca 14.5ml is required
10mins and allow it to stand overnight. When After complete removal of K chlorate,
necessary, remove a portion required for swirl the crucible once with l.Oml of soln
complete test, filter it before using and No 2 and remove the liquid immediately by
transfer to a burette suction. Wipe the bottom of crucible with
Soln No 2. Add to ca 400ml of distd w in a tissue paper, dry the crucible in an oven at
one-half liter amber glass bottle, l.Og of Pb 80~ 1° for 30mins, cool in a desiccator and
thiocyanate, l.Og of Sb sulfide & l.Og of weigh
LA; insert a rubber stopper, shake vigorously %KC103= (100 B)/W,
for ca 10mins and allow it to stand over- where B = loss in wt of the contents of
night. Filter before using a portion required crucible and W= wt of the sample on a
for complete test and transfer to a burette moisture-free basis
Procedure. “Weigh a Ig sampl e(previously For detn of other ingredients: Sb sulfide,
dried ar ca 65°) in a tared 30ml sintered glass LA & Pb thiocyanate, see Ref 12,pp 7-9
crucible of medium porosity, add from the If the mix does not contain Pb thiocyanate
burette 3.Oml of soln No 1 and swirl the the wash solns do not contain any thiocyanate
crucibIe for exactly Imin taking care not to and in some cases the washing may be con-
spill any liquid. Remove the liquid by suction, ducted by using LA-satd distd w as described
 C 197

in Ref 12,p 9 mp 147° with decompn; sol in w or ale; insol

For an igniting mix consisting of K in nondissociating org SOIVS; was prepd by
chlorate 55 and Pb thiocyanate 45 Y., the heating a coned aq soln of HC103 on a water
thiocyanate is detd first by the method bath with a S1 excess of pyridine, This
described in Ref 12,p 10 and Kchlorate is cc,mpd burns with a sudden flash when
calcd by subtracting Pb thiocyanate content touched with a flame or in contact with coned
from 100 H $04
For primer mix No 70, the ingredients: Re/s: l)Beil 20,(58) 2)R.L.Datta & J.K.
TNT, Sb sulfide and Pb thiocyanate are detd Choudhury, JACS 38, 1083-84(1916)
as described in Ref 13, while the remaining Quinoline Chlorate, HC=CH- C–N=CH
ingredient
subtracting
K chlorate + gum is calcd by
from 100 the sum of other ingredients I II ~ .HC1O,
HC=CH- C-CH=CH
Re/s: l) Faber 3(1919), 141-50 2)C..A.Taylor
mw 213.62, N 6.56%; yellowish hygr trysts,
& Wm. H. Rinkenbach, “Explosives”, USBur- mp 66-7°; sol in w or alc but cannot be
MinesBull 219 (1923), 32-61 Analysis of recrystallized from these SOIVS; was prepd by
commercial K chlorate); 142-3 (Detn of K
heating an aq soln of HC103 with a S1 excess
chlorate in dynamites) 3)Scott .& Furman
of quinoline and purifying the prod by washing
(1939), 274-6, 861-70, 1677 & 2160 4)
with a mixt of alc & eth. This compd decomp
Treadwell & Hall, vols 1 & 2(1942) 4a)
with a flash and a large amt of smoke when
Kast-Metz( 1944), 373-80 (Analysis of commer-
touched with a flame or in contact with coned
cial K chlorate) 5) Anon, “Control Laboratory
HJ04, leaving a blk residue
Manual”, Expls & Proplnts Branch, PicArsn,
Re/s: l)Beil 20,(136) 2)R.L.Datta & J.K.
Doverv NJ (1956); Method No 501. l(Analysis
Choudhury, JACS 38, 1084(191.6)
of M31 Igniting Mixture); Method No 502.1
(Analysis of PA-100 Primer Mixture); Method Silver Chlorate, AgC103; mw 191,34; exists
No 503. l(Analysis of Standard Primer Mixture) in two forms: stable wh, opaque tetragonal
6)M.Halik & R.Croom, PATR 2430(1957)(U) prisms(d 4.42-4.44) and labile cubic trysts
(Flame spectrophotometric method for detg (d 4.21); mp 230°, bp dec at 270°, evolving
Na chlorate in K chlorate) 7) Anon, ‘ ‘Analy- oxygen; sol in w or ale; was prepd in 1802
tical Methods for Powders and Explosives”, by R.Chenevix(See in Ref 2), by passing
AB Bofors Nobelkrut, Bofors, Sweden(1960), chlorine gas into w in which silver oxide was
1.48-9(Analysis of commercial K chlorate); suspended. It can also be prepd by dissolving
150(Colorimetric detn of chlorates in K Ag20, or finely divided metallic Ag, in
perchlorate) 8)Vogel, InorgAnalysis( 1961), chloric acid(Ref 2). Its method of prepn from
313,361-2,399,412,560-4,571,723 &.885 9) AgNO~ & NaC103 is described by Nicholson
A. R. Lusardi, “Laboratory Manual”, Expls & & Holley(Ref 5)
Proplnts Lab, PicArs,n, Dover, NJ(1962), Silver chlorate is a strong oxidg agent and
Methods 202,203,204,205,206,208 & 209 forms powerful expl mixts with combustible
(Analyses of primer and igniter mixts contg materials. According to A. Wtichter(See in Ref
K chlorate) 10)US Military Specification 2), silver chlorate alone can decomp explosive-
MIL-P.150A(K chlorate for use in ammunition) ly when heated very rapidly
1 l)US Joint Army-Navy Specification JAN-P Bruni & Levi(Ref 1) prepd an expl compd
l 21 7(or PA-P D-254 )(Detn of K chlorate in K Triamminesilver Chlorate, AgC103.3NH3, by
perchlorate) 12)US Military Specification the action of ammonia on AgC103
MlL.D-2493(Superseding PA-pD-l W(Analy- Re/s: l)G.Bruni & G. Levi, Gazz 46 II, 17
ses of various primer and ignirer mixts) 13) (1916) 2)Mellor 2(1922), 340 3)Gmelin,
US Military Spec MIL-P-20449A(Ord)( Superseding Syst Nr 6(1927), 339-40 4)Ullmann 3(1929),
MIL-E-20449)(Analy sis of No 70 primer compn) 299 5)D.G.Nicholsont & C. E. Honey, Jr,
Inorg Synth 2(1946), 4-6 6)Sidgwick,
Pyridine Chlorate, HC —N—=CH ChemElems 1(1950), 128 7)Sax(1957), 1104
I . HC103; 8)F.A.Warren .et al, ‘ ‘Chlorates and
II
HC—CH ‘-CH Perchlorates”, NAVORD Rept?7147(VOI 1)
mw 165.56, N 8.56%; wh crysts(from alc) (1.960), 141
having soft, soapy touch & odor of pyridine, Sodium Chlorate, NaC109; mw 106.45; reported
 C 198

in Mellor(Ref 3) to be tetramorphous, forming: not used in older expl compns until a method
a)cubic .b)unstable rhombic c)unstable was found to waterproof the substance. ,This
monoclinic and d)rhombic. or pseudo-cubic was achieved by coating the grains of Na
crystalline forms; COI, odorless cubic trysts chlorate with oily, greasy or plastic materials
are the common form; mp 248-61°, bp decomp; (such as castor oil, vaselin, paraffin, etc)
o
d 2.490 at 15 ; n~ 1.515 at 20°; sol in w, ale, and the resulting expls became known as
alkalies, and aq solns of NaCl, glycerol and CHEDDITES(qv), also called Streecites or
liq ammonia(Ref 3)(See also Refs 5,6,11 & Street Explosives. Some of these expls were
18b) used by the French during WWI for military
Methods of prepg NaC103 are the same as purposes, such as demolition work and for
those for KC103, except that Na salts are loading grenades, mines and trench mortar
used. Detailed description of methods of bombs. ,Coating of grains not only rendered
prepn are given in Refs 1,5 & 11. The present them less hydroscopic but it also made them
coml method is by electrolysis of hot coned less sensitive. to friction and impact(See also
aq soln of NaCl(Refs 8,9 & 11) Refs 1,6 & 11). Babor(Ref 8) waterproofed
Sodium chlorate decomp when heated or the trysts of ~a ‘chlorate by coating them
in contact with combustibles or coned acids, with 4% collodion s oln, followed by drying.
in the same manner as the potassium salt. Several expl compns contg Na chlorate and
Although it is a powerful oxidg agent and combustible materials were patented in France
contains more oxygen per unit wt than KC103, after WWII(Ref 13). A Na chlorate expl
it has not found wide use in expls due to its developed during WWII by Kiernan & Bowen
extreme hygroscopicity & high sensitivity. was tested at PicArsn and found to be
According to Faber(Ref 2), one of the principal unsuitable for military purposes(Ref 10a).
reasons why NaCIO~ is dangerous is. due to Some Ger Na chlorate expls, such as
the deliq & subsequent effl of the material Chloratits, Gesteins-Koronits and
causing segregation of fine trysts which are Miedziankit, are listed in Ref 18a. NaCIO ~
highly reactive. An expln which cost the lives has also been used in manuf of matches(Ref
of 4 persons and injured several others 12) and in some pyrotechnic compns(Ref 20).
occurred in the chemistry bldg of Howard Kirk & Othmer(Ref 11) lists its principal uses
University, Washington, DC on 27 March 1952. as an intermediate in the manuf of perchlorates
The blast resulted when ca 400 lbs of sodium and in weed killers
chlorate was being removed from a basement CPCEM(Compagnie de produits chimiques
storage room(Ref 16). ,The investigating. et ~lectrom~tallurgiques ) Alais, Frogues &
committee reported that a static elec spark, Camargue patented recently [ FrP 992332(1951)
believed to have been generated when a worker & CA 50, 1102o(1956)] , a pyrotechnic mixt
grasped the metal handles of the loaded hand of a chlorate or a nitrate and tat, such as
truck, caused the expln & fire. The report Na chlorate 80 & tar 20% made in the form of
recommended NaC103 should never be stored a rod 6mm in diam and 170mm long, covered
in a general storage area, but it should be with a O. lmm synthetic resin layer. The
stored for lab use in glass bottles contg not rwl burns for 95sec developing a temp of
over l-lb(Ref 17) 1400=1600°. Immersion in water for 3hrs did
Details concerning the props, hazards and not impair its burning characteristics
percautions in handling & storing NaC103 US Military Spec(Ref 21) covers the
are discussed by Mattair(Ref 15) and in MCA reagent-grade Na chlorate and the requirements
safety booklet(Ref 14) are:
Explosive Properties. They are comparable a)NaC103 content, minimum 99%
to those of K chlorate. Expls contg NaC103 b)Insolubles, maximum 0.010
posse ss slightly higher power than those contg an c)Bromate(as Br09 ), max 0.07
equal proportion of KC103. For example, d)Chloride(as Cl), max 0.005
among the expls listed by L. M4dard, MP e)Nitrogen compds(as N), max 0.001
32,. 210(1950), the one contg 90% NaC103 f)Sulfate(as S04), max 0.003
& 10% paraffin is about 8% more powerful than g)Ca,Mg & Amm hydroxide 0.01
the corresponding expl contg KC103 precipitate, max
Uses: Na chlorate, being hydroscopic, was h)Heavy metals(as Pb), max 0.001
 C 199

i)Iron(as Fe), max 0.0005 nitrate, may be used

j)Form Crysts Na chlorate intended for US military use
k)Color Colorless is analyzed as prescribed in Ref 6. The
Accdg to Belgrano(Ref 16a) a good Na procedures are as follows:
chlorate, suitable for Cheddites should possess A)NczC103 content. Weigh accurately a O.lg
the following properties: NaC103 min content sample(previously dried over coned sulfuric
99. 50%, NaCl max 0.05%s in solubles max 0.04%, acid for 24hrs) and dissolve it in 10ml distd
and moisture max 0.07% w in a 250ml Erlen fl. Add 35.Oml of acid
Refs: l)Escales, Chloratspr(1910), 41,61 & ferrous sulfate soln(prepd by dissolving 7.00g
128 2)H.B.Faber, ‘tMilitary Pyrotechnics”, of ferrous sulfate in 90ml freshly-boiled distd
US GovtPrintOfc, Washington, VOI 3(1919), w and addg sufficient amt of coned suIfuric
128ff 3)MeHor 2(1922), 325 4).C.A.Taylor acid to make 100ml), close the flask with a
& W.H.Rinkenbach, “Explosives”, USBur- stopper provided with Bumsen valve and boil
Mine sBull 219, Washington(1923), 36 5) gently for 10mins. Cool, add 10ml of 10%
Gmelin, Syst Nr 6(1927), 337, 340 6) manganous sulfate soln and titrate the excess
IJllmanrt 3(1929). 298 7)Stettbacher 1(1933), ferrous sulfate with O. lN K permanganate soln.
314 8)M.Babor, BuHSectSciAcadRoumake Run concurrently a blank with 35 .Oml acid
19, 213-18(1937-38) & CA 34, 5661(1940) ferrous sulfate
9)A.L.Pitman et al, ChemMetEngrg 45, 692-96 %NaC103= [(A-B)x 0.1774]/W,
( 1938)(Production of sodium chlorate by where A ml of K permanganate
q soln used in
electrolytic method) 10)Davis(1943), 357-66 the blank, ,B = ml used in the sample test and
10a) J. Phillips, PATR 1277( 1943 )( Study of W= wt of sample
NaC103 explosive developed by Kiernan & B)lnsoltibles, Dissolve a 10g sample in 10ml
Bowen) ll)Kirk & Othmer 3(1949;, 70916 of hot distd w, heat on a steam bath for lhr,
12)CondChemDict( 1950),604 l~)EtatFran$ais, filter thru a tared sintered glass crucible,
FrP 971644(1951) & CA 46, 9311(1952) ri~se it with hot w, dry at 105?3°, cool in a
14)Anon, Manufg Chemists Ass~c, Chemical desiccator and weigh
Safety Data Sheet SD-42 (1951),1 lpp & CA C) Chlorz”de. Dissolve exactly 2.000g of sample
46, 5319(1952) 15)R.Mattair, .paperInd 33, in 40ml of hot distd w, (contained in a 100ml
1187-88(1952) & CA 46, 3761(1952) 16) Anon, Nessler tube), cool, add 5 drops of nitric
C & EN 30~ 1416 & 1420(1952) 16a)Belgrano acid(free from nitrogen oxides) and lml of Ag
( 1952), 178(Na chlorate for Cheddites) 17) nitrate(prepd by dissolving 1.700g of AgN03
:.
0.R.Ewing, C & EN 30, 3210(1952) & CA m sufficient w to make 100ml). Prepare a blank
46, 9845( 1952) (Abstract incorrectly lists site in another Nessler tube with 40ml of w, 5 drops
of expl as Catholic Univ instead of Howard of nitric acid, lml of Ag nitrate and O. 10mg
Univ) 18a)PATR 2510( 1958)zP Ger 28(Table of NaCl(or lml of a soln contg O. 1649g NaCl
8) & Ger 69 18Sax(1957), 1114 18b)Cond- in 1 liter). If the turbidity in the sample tube
ChemDict( 1961), 1037 19) F. A.Warren et al, is greater than in the blank, the material does
“Chlorates and Perchlorates”, NAVORD not comply with requirement of Ref 6
Rept 7147(V01 .1)( 1960J 67-8 20) Ellern, D)Brornate. Dissolve exactly 2.000g of sample
Pyrotechnics(1961), 148,171,256 & 259 21) in 200ml of freshly boiled and cooled w in a
US SpecificationNIL*$11169 (Requirements for glass-stoppere.d flask, add 10.Oml of lN HC1,
Na chlorate, reagent grade) mix, and add 10ml of freshly prepd 10% ICI
Sodium Chlorate, Analytical Procedures. soln followed by 5ml of freshly prepd starch
Chlorate ion may be detected and detd as , indicator. Stopper immediately, swirl gently
described under Chlorates, Analytical to mix the contents and allow it to stand for
Procedures. Sodium ion may be detected by lhr protected from light. Titrate with O.lN Na
the color it imparts to a flame, or by means thiosulfate solution until the blue color
of the spectroscope. The procedure is described disappears. If more than 0.65ml of thiosulfate
in Ref l,p 875( See also Ref 2). For quantitative is required, the material does not comply with
detn of Na, it can be precipitated as Zn-, Mg-, requirement of Ref 6
Co- or Ni-, uranyl acetate as described in E)Nitrogen compounds, Dissolve exactly
Refs 1,2 & 5. Other methods, such as pptn as 2,000g of sample in 40ml distd w, add 1.000g
Na pyroantimonate or as Na cesiumbismuth of powdered Devarda’s metal and 20ml of 10%
 C 200

NaOH. Stopper the flask and, after allowing separate. Prepare a control by mixing 0.50ml
it to stand in a cool place for 2hrs, distil of the soln contg 0.005mg of iron [ prep.d by
40ml, collecting the distillate in 5ml of w dissolving 0.08635g of NH4.Fe(S04)2. 12H20
contg 1 drop of dil HC1. Add to the distillate in 10ml of 10% sulfuric acid and adding
lml of 10% NaOH and 2.Oml of Nessler’s soln sufficient w to make 100ml] with 10ml of w,
(prepd as described in Ref l,p 630, Footnote lml of 37% HCI, 15ml of butanolic K thio-
2). Prepare a control with 0.02mg of nittogen cyanate, shake vigorously and aHow it to
by treating 2ml of a soln contg 0.0382g of separate. If the red color in butanol layer
NH4 Cl in 1000ml of w in the same manner in the sample mix is darker than the control,
as the 2g sample. If the color of test soln is the material does not comply with spec
darker than the control, the sample does not requirement
comply with spec requirement Kaye(Ref 3) describes a method for detn
F) Sul/ate. Dissolve exactly 3.000g of sample of purity of Na chlorate by titration in non-
in 100ml of w, add lml of 1O$ZHC1 and 5ml of aqueous medium and Halik & Croom(Ref 4)
Ba chloride soln(prepd by dissolving 12.00g give a flame spectrophotometric method for
BaCl * in ‘sufficient w to make 100ml). Allow detg Na chlorate in K chlorate
it to stand overnight and if any turbidity or ppt Re/s: l)Scott & Furman(1939), 875-8 2)
forms, the sample does not comply with Treadwell & Hall(1942), VOIS 1 & 2 3)S.
requirements of spec Kaye, PATR 1947( 1953) (Detn of purity of
G)Ca, Mg and Armn hydroxide precipitates. inorg compds of ordnance interest by titration
Boil a soln of 10.00g sample in 50ml of w and in nonaqueous medium) 4)M.Halik & R.
15ml of 37% HC1 until no more chlorine is Croom, PATR 2430(1957) 5)Vogel, Inorg-
evolved. Dilute” to 120ml with w, heat to Analysis(1961), 557-9, 663, 722-3 & 885
boiling, add 5ml of Amm oxalate soln(prepd 6)US Military Specification MlL=S-l 1169(tests
by dissolving 4.000g in sufficient w to make for Na chlorate, reagent grade)
100ml), 3ml of Amm phosphate soln(prepd by Strontium Chlorate, Sr(C103)2, mw 254.54; wh
dissolving 13.00g of dibasic Amm phosphate rhrnb trysts, mp dec 120°, d 3.152; sol in W,
in sufficient w to make 100ml) and 20ml of insol in ale; was obtd in 1843 by A. W%chter
28% Amm hyd?oxide. Allow it to stand over- (See in Ref 2) on warming, over coned H2S04,
night and if a ppt is present, filter, wash with a soln obtd by neutralizing aq HC103 with
2.5% Amm hydroxide and ignite. If the wt of either Sr(OH)2 or SrC03. The anhyd salt may
the residue exceeds 0.00I0g, the sample does also be obtd by heating the octahydrate or
not comply with requirements of spec other hydrates to ca 120°. Monobydrate,
H)Heavy metals. Evaporate to dryness on a Sr(C103 )2.H20, is listed in Ullmann(Ref 2).
steam bath a mixt of 5.000g of sample with Trihydrate, Sr(C103 )2.3H20, is reported in
15ml of hot w & 10ml of 37% HCI. and dissolve Mellor(Ref 1) as having been obtd by A.
the residue in 50ml of w. Treat 10ml of this Potilitzin in needle-like trysts by cooling
soln with 2ml of the soln(prepd %y dissolving a 59% soln of strontium chlorate to -40°, and
0.0160g of Pb nitrate in 1000ml of w)which is rhmb prisms by cooling a 6470 soln to -20 to
equivalent to 0.02mg of Pb, dilute to 30ml 25°. Octabydrate, Sr(C103 )2.8H20; mw 398.67;
with w and add lml of lN acetic acid(Soln A). wh ndls, mp(looses 8H20 at 120° & decomp
Treat 30ml of original 50ml soln with lml of at 2900); sol in w, S1 sol in ale; coml salt
lN acetic acid and designate it as Soln B. can be prepd either by electrolysis of strong
To both solns add 10ml of freshly -prepd satd aq soln of SrC12 or by passing chlorine gas
aq sohr of hydrogen sulfide and if Soln B is thru a warm aq soln of Sr(OH)2 with subsequent
darker than Soln A, the sample does not evapn of the w and crystn of the octahydrate
comply with spec requirement Uses: The octahydrate is used as an oxidg
l,)lrorz, Add to the remaining 10ml from the agent in expls, exercising a cooling effect
test H, 15ml of butanolic potassium “thio- due to the large amt of w of crystn, and in
cyanate soln(prepd by dissolving 10.00g of pyrotechnic compns for producing a red light
K thiocyanate in 10ml of w, warming to ca (Refs 3a,4,5a & 7). Izzo(Ref 4a) gives the
30°, adding sufficient n-butanol to make following compn for violet light star: Sr
100ml and shaking vigorously until clear), chlorate., 14.5, K chlorate 58.5 , Cu car-
shake vigorously for 30secs, and allow it to bonate 10, sulfur 10 & shellac 7%
 C 201

Re/s: l)Mellor 2(1922), 345 2)Ullmann 3 explodes ca 88°; sol in w or ale; insol in eth
(1929), 299 3)Gmelin, Syst Nr 29(1931), 143ff or benz; was prepd by addg an aq soln of
and Nr29(1960),220ff 3a)Davis(1943),86 chloric acid dropw~se to a S1 excess of o
4)CondChemDict( 1950), 629 4a)Izzo, -toIuidine, care being taken not to add an
Pirotecnia( 1950), 215 5)Sidgwick, ChemElems excess of HC103 as the presence of a little
1 (1950)+ 257 5a)Shidlovskii( 1954), 27-8 free acid will decomp the mixt explosively, even
6)Sax(1957), 1138 7)CondChernDict( 1961), at RT. This compd is not indefinitely stable
1080 8)Ellern, Pyrotechnic s(196 1)-not found in air, turning gray & finally blk on long
standing. It burns explosively in contact with
Strontium Chlorate, Analytical Procedures.
a flame
Chlorate ion may be detected and detd as
Re/s: l)Beil 12,(374) 2)R.L.Datta & J.K.
described under Chlorates, Analytical
Choudhury, JACS 38, 1080-81(1916)
Procedures and strontium ion as described
in Refs 2,3 & 4. The complete analysis of p-Toluidine Chlorate, CO1 crysts(from ale),
salt may be done in the manner described by mp expl at 125°; sol in ale; nearly insol in
Faber(Ref 1) for Ba chlorate. The method is eth or benz; was prepd by addg an aq soln of
HCIOa dropwise to an ethereal soln of p-tol-
outlined here under Barium Chlorate, Analy-
uidine, taking care to keep the p-toluidine in
tical Procedures. There is no US Military
S1 excess. This compd on exposure to air
Specification
Re/s: l) Faber, Pyrotechnics 3(1919), 160-4 gradually turns gray due to slow decompn of
the salt. It takes fire suddenly in contact with
2)Scott & Furman( 1939), 899-902 3)Treadwell
a flame and emits a large. amt of wh fumes
& Hall( 194,2), Vols 1 & 2 4)Vogel, Inorg
Re/s: l)Beilstein 12;(411) 2)R.L.Datta &
Analysis(1961), 552-3
J. K. Choudhury, JACS 38, 1081(1916)
Tetramethylammonium Chlorate, N(CH3)4..
Trimethylsulfine Chlorate, S(CH3)3 .C103;
C103; mw 157.59; N 8.89%; wh trysts, mp
mw 160.63; col hygr crysts(from w), mp
explodes at 230°; SOI in alc or w; was prepd
explodes at 170°; very sol in w; was prepd by
by double decompn of tetramethylammonium
double decompn of AgC103& trimethylsulfine
iodide & AgC103 and evapg the soln on a w
iodine, and evapg the soln on a w bath. This
bath to crystn. This compd suddenIY flashes
salt liquifies when exposed to air, and
in contact with a flame or in contact with
explodes violently on heating or in contact
coned H2S04(Refs 1 & 2)
with a flame
Datta & Choudhury(Ref 2) also prepd
Re/s: l)BeiI 1,(144) 2jR.L.Datta & J.K.
Tetrwethylarnr,voniurn Chlorate, N(C2H~ )4-
Choudhury, JACS 38, 1085(1916)
C103, wh trysts, mp 223 °(dec); and Tetra-
propylurnrnorzium Chlorate, N(C ~H7)4C103, Zinc Chlorate, ZnC103; its prepn is given in
wh trysts, mp 217° but neither salt is expl, MeHor(Ref 1) and in Gmelin(Ref 2)
However, they both take fire easily when in Dihydrate, Zn(CIO~ )2.2H20; mw 268.27; COI
contact with a flame or coned H 2S04 polyhedral trysts; can be obtd by allowing
Re/s: l)Beilstein 4,(326) 2)R.L.Datta & J.K. the tetrahydrate salt to stand at 65° for some
Choudhury, JACS 38, 1084-85(1916) time; its prepn is described in Gmelin(Ref 2).
Tetrabydrate, Zn(C103) .4H20; mw 304.36,
Thallous Chlorate, TIC103; mw 287.85; CO1 6
CO1, deliq trysts, mp 55 , bp dec, d 2.15;
needle-like trysts, mp dec, d 5.505 at 9°;
can be obtd from the hexahydrate salt
SI sol in cold w, readily sol in hot w; was
Hexahyclrate, Zn(C10~)2.6H20; mw 340.39;
prepd by dissolving the metal in chloric acid,
CO1 monoclinic trysts, mp 60°, bp decomp;
or by mixing KC103 & thalIous nitrate, or as
was prepd by action of chloric acid on zinc
recommended by J. Muir(See in Ref 1) by the
carbonate, by action of Ba(C103 )2 on ZnS04,
interaction of Ba(C103)z & thallous sulfate.
and by action of Zn fluQsilicate on KC103.
This compd is an oxidg agent which when
It gradually passes at 14-15° into the
heated forms thallic perchlorate
tetrahydrate salt
Refs: l)Mellor 2(1922), 355 2)Sidgwick,
All of the zinc hydrated chIorates are
ChemElems 1 (1950), 487 3)Sax(1957), 1175
very sol in w, ale, glycerin or ether. They,
o-Toluidine Chlorate, CH3.C6H4 .NH2+ HC103; like other inorg chlorates, are also oxidizers
mw 191.62, N 7.31%; CO1 pltlts(from ale), mp which readily explode in contact with com-
 C 202

bustible materials (or its substitute, Na chlorate) found no

Uses: In the book of CundiII(1889J available application in expls or proplnts but was used
at PicArsn in the French translation [MP in percussion caps, where high sensitivity
5, 333(1892)] is described an older expl is a desirable property. One of the mixts
“Extradite” which was based on Zn suit able as a primer c ompn was Augendre
chlorate and AN Powder(See Vol 1 of Encyclopedia,p A507-L),
Ephraim & Jahnsen(See in Ref 2) prepd, proposed in 1849. This mixt was, however, too
by action of ammonia on zinc chlorate, two sensitive for use as .an expl or a proplnt. In
ammines which are expl: Tetrammirzezirzc(ll) 1871, H. Sprengel of Germany partially solved
Chlorate, [ Zn(NH3)4] (C103)2, CO1 trysts; the problem of densitization by adopting a
and Hexamminezin~ll) Chlorate, [Zn(NH3)6] - method in which the chlorate was not brought
(C10~)2, CO1 trysts which lose NH9 at RT and into contact with combustible ingredients of
pass into the tetrammine deriv(See Vol ~, intended mixts until ready to fire. He made
Table F,p A282) up K chlorate into porous cartridges and then
Re/s: l)Mel.lor 2(1922), 349-50 2)Gmelin, dipped them into liquid combustible materials
Syst Nr 32(1924), 176 & 32(1956), 882 3) just before use. These expls were, however,
Ullmann 3(1929), 299 4)CondChemDict. inconvenient to handle. The expls introduced
( 195o), 714 5)Sidgwick, ChemElems 1 (1950), in France in 1881 by E. Turp.ti under the name
277 6)SSX(1957), 1267 of “Poudres i double effet”( “Double Effect
Powders”), which contained tar as a
CHLORATE EXPLOSIVES combustible and desensitizer, were more con-
Chlorate Explosives are mixts of chlorates venient to handle and could be manufd before
(chiefIy K or Na) with various combustible use. These expls, and later exp.1.s of Turpin
materials, such as oils, greases, paraffins, (1888), known as cCPyrodialites” were not,
liquid nitrocompds, carbon, charcoal, etc. however, as good as the expls patented in
Many of these mixts ace known and were used 1897 by Street, now known as Cheddites
in Europe, since 1850’s. Some of them> such Following is the list of chlorate expls
as Cheddites, are still in use. Some of these which are or will be described in this
expls, such as Rack-a-Rock, Rendrock & Encyclopedia:
Vigorites were used in the US, but as far as Alkalsit.. See PATR 2510 (1958), Ger 3-R
is known, chlorate expIs are not used now in Almatrites. See Vol l+ A140-L
the US, being replaced either by AN or Asphalines. See Vol l,p A496-L
perchlorate mixts Augendre Powder. See Vol l,p A507-L
Historical. Since the discovery of potassium Azobenzene Cheddite Type Explosives, See
chlorate by C. L. Berthollet(in 1780’s) Vol 1, A647-L
attempts have been made to utilize it in expl Bakufun. See Vol 2,p B5-L
mixts, chiefly as replacement for potassium Barbarit. See Vol 2,p B19-R
nitrate in Bkpdts. K chlorate is not only a Baron & Cauvet Explosives. See Cauvet &
powerful oxidizer but it can also be detonated Baron Explosives
alone if allowed to fall, while in a molten state Bayon Powder. See Vol 2,p B26-L
on a red-hot iron plate. The first expl Bellford Powder. See Vol 2,p B32-R
utilizing K ~hlorate was prepd by BerthoHet Benedikt Explosives. See Vol 2,p B33-L
(See. Berthollet Powder in Vol 2 of Encyclopedia Bengaline. See Vol 2,p B33-R. This expl
p B 107-L). This was a much more powerful & patented in 1882 by Mendail is erroneously
brisanr expl than BkPdr, but too dangerous called by Pfrez Ara(Ref 15,p 211)c’Benzalina”
to handle on acct of its extreme sensitiviness Berthelot Powder. See Vol 2,p B 106-L
to friction and impact. This mixr often explod- Berthollet Powder. See Vol 2,p B 107-L
ed during its manuf, or prematurely in firearms. Bjorkmann Explosives. See Vol 2,p B 165-L
After disastrous explns, which took place in Boritines. See Vol 2,p B250-R & Ref 4,p 81
France in 1788 and 1792 during pulverizing Brain Powders. See Vol 2,p B 260-L & Ref 3,p
and mixing of ingredients(K chlorate, sulfur 359
& carbon), the manuf of powders contg K Brank(von) Powders. See Vol 2,p B261-L &
chlorate was prohibited in France. Ref 20,p Ger 23
In the following 50-60 years K chlorate Briggs Explosive( 1909). See Vol 2,p B 265-L
 C 203

Britainite. See VOI 2,p B300-R. A different Davey Powders(1852). See Ref Ia,p 314; Ref
compn:KC103 72.0, AN 20.7 & naphthalene 4,p 76 & Ref 21,p 393
7.3% is given in Ref 21,p 395 Davies Powder(1860). See Ref la,p 315; Ref
Brown’s Powder. See Vol 2,p B 3 18-R 2,p 180 & Ref 21,p 391
Callou Powder. Mixt of KC103 & AS2S3 DeCustro Powders( 1883). See Ref Ia,p 317 &
(otpiment). See Ref 3,p 262 Ref 2,p 183
Canouil Powder. See Vol 2,p C39-R; Ref la,p Delhorbe Explosive. See Ref 2,p 184
303 & Ref 2, 108 Demetriade, J onesen & WiHiam Explosive
Carlit(or Karitto) Explosive(1906). See (1905). See Ref 21,p 398
VOI 2,p C68-R & Ref 21,p 399 D4signolle & Casthelaz Powder. See Casthelaz
Castan(Poudre v6gt$tale)(1884). See Vol 2,p & D6signoHe Powder
C83-R; Ref la,p 305; Ref 2,p 782(as Dickson P owder( 1895). See Ref 2,p 205
V4g.4tale) & Ref 2,p 394 DistIer, E?lecher & Lopez Explosive. See Ref
Casthelaz & D~signolle Powder( 1867). See 7,p 259
VOI 2,p C84-L; Ref 2,p 189(as Dc$signolle & Divine Explosives, such as Rack-a-Rock. See
Casthelaz) & Ref 21,p 392 Ref Ia,p 76; Ref 2,p 667; Ref 3,p 265; Ref 5,p
Castro Powder( 1884). See Vol 2,p C88-R; Ref 379; Ref 7,p 135; Ref 15,pp 231-3 & Ref 21,p
la,p 305; Ref 2,p 118; Ref 15,p 213 & Ref 393
21,p 394 Domergue ExpIosive(1889). See Ref 2,p 207 &
Catactine(or Chandelon) fixplosives( 1888). Ref 21,p 395 Donar.
See Vol 2,p C88-R; Ref la,p 306; Ref 2,p 118; Donar. One of the expls patented in Russia by
Ref 7,pp 695-6 & Re f 21,p 395 FiedIer. See Ref 2,p 300 & Ref 3,p 266
Cauvet & Baron Explosives. See Vol 2,p Double Effect Powders(of Turpin). See Ref
C91-R & Ref 21,p 394 lb,pp 105-6 & Ref 2,pp 777-8
Chakoor Powder( 1903). See VOI 2,p C 146 & Dulitz Explosive( 1886). See Ref 1a,p 323 &
Ref 21,p 398 Ref 2,p 209
Chandelon Explosives. See Catactine Duplexite(of Turpin). See Ref lb,p 108; Ref
Chapman Explosives 1888). See Vol 2,p 2,p 210; Ref 4,p 81 & Ref 21,p 395
C148; Ref la,p 306& Ref 2,p 127 Dynamogene(1882). See Ref la,p 327 & Ref 2,p
Chauvet Powders(1882). See VOl 2,p C 155 & 231
Ref 21,p 394 Edmunds Explosives(1893). See Ref 2,p 238
Cheddites. See Vol 2,pp C 155 Egelit. Same as Miedzianki.t(Ref 8a,p 61)
Chloratit. See VO1 2 & Ref 20,p Ger 28-L Ehrhardt Powders( 1864 & 1865). See Ref la,p
Chlorat-Rivalit. See Vol 2 & Ref 8a,p 82 330; Ref 2,p 238; Ref 3,p 263 & Ref 15,p 214
(under Rival it) Ennayaku. See Addnl Ref U,p 28( in this section)
Chloratzit. See Vol 2 & Ref 8a,p 21 Entoyaku, See Addnl Ref U,p 28(in this section)
Cicene. See Cycene Evangelidi Explosive(1904). See Ref 21,p 398
Clarite. See Vol 3 & Ref 2,p 143 Explosifs O & OC. Same as Cheddites
Clement or Fuchs Powders. See Vol 3 & Explosif 03, Same as Prometht?e
Ref 2,pp 145 & 310 Explosif P. One of the Cheddites based on K
Colliery Cheddite. See Note C in Table 3 chlorate(See Table 3, under CHEDDITES)
under CHEDDITES Explosif S. One of Cheddites based on Na
Colliery Steelite. See Vol 3 & Ref 5,p 383 chlorate(See Table 3 under CHEDDITES)
Columbia Powder. See Vol 3 & Ref 21,p 395 Explosive Papers(Papiers explosibles in Fr).
Comet Powder. See Vol 3 & Ref 15,p 211 See Ref lb,pp 62-4; Ref 2,pp 436,599,604 & 665
Cornet Powder. See Vol 3 & Ref 21,p 399 and Ref 15,p 213
Coronite or Koronit. See Vol 3 & Ref 8a,p 55. Extralite. See Ref la,p 333
Ref 20$p Ger 32 Fahrm Explosive(1898). See Ref 2,p 294
Cotter Powder. See Vol 3 & Ref 21,p 399 Fallenstein Explosive(1884 & 1886). See Ref
CSE Explosives. See Vol 3 & Addnl Ref W,p la,p 334 and Kinetite
21 l(in this section) Fenton Powder(1873). See Ref l,p 335; Ref 2,p
Cycene(Cicene) Powder. See Vol 3 & Ref 21,p 298; Ref 3,p 264; Ref 15,p 212& Ref 21,p 392
395 FieIder Explosives(1901). See Ref 2,p 300;. Ref
Dapremont Powder( 1877). See Ref 21,p 393 3,p 266 & Ref 15$p 231 and also Donar
 C 204

Flerlet Powder( 1870). See Ref 21,p 392 Hassia-Chlorat. See Ref 8a,p 48
F Iobert Ammunition. See Ref 8a,p 40 Hawkins Explosive( 1895). See Ref 2,P 37’0
Fluorine of Turpin. See Ref 2,p 302 Hawkins Brothers Explosives 1896). See Ref 2,P
Fontaine Powder(1896). See Ref la,p 336; Ref 370 & Ref 21,p 391
2,p 616(under picrates) & Ref 21,p 397 Hercules Dynamite. See Ref lb,p 12 & Ref 2,p
Fontana, Barelly & DeChoisy Powder(1869). 374
See Ref 21,p 392 Himalaya Powder or Himalayite( 1906). See
Fr3nkel Explosive. See Ref la,p 338 & Ref Ref 8a,p 51 & Ref 21, P 399
2,p 309 Himly Powder. See Ref 2,p 375; Ref 15,p 216
Fuchs(or Fux) Powder. See Ref la,p 339; Ref & Ref 21,p 400
2,pp 145 & 31% Ref 21,P 399 Himly and Von Triitschler-F alkenstein Powder
Gelatin-Cheddites. See Table 4 under (1869). See Ref 2,P 375
CHEDDITES Hochst?itter Powder( 1869), See Ref lb,p 14;
German Chlorate Explosives. See Ref 20,pp Ref 2,p 376 & Ref 21,p 392
Ger 3,23,28,32 & 69 Horsley Dynamites(1872). See Ref lb,p 14 &
German Chlorate Primary Mixtures. See Ref 20,p Ref 2,p 71?
Ger 136 Horsley Powder. See Ref 21,p 392
German ChIorate Pyrotechnic Mixtures. See I-Iowittite. See Ref lb,p 15 & Ref 2,p 372
Ref 20,p Ger 154 Ievler(or Jewler) Explosives 1897), such as
Gerresdorfer & Bals Powder( 1892). See Ref 2,p Prometh~e or Explosif 03. See Ref 2,p 382
341 & Ref 2L,P 395 & Ref 15,P 231
Gesteins-Koronit. See Ref 14,p 364 & Ref 20,p Jahnite(or Jahline). See Johnite
Ger 69 & table 22 Jewler Explosives. See Ievler Explosives
Giedyuim Powder(1868). See Ref 21,p 392 Johnite Explosive. See Ref lb,p 16 & Ref 2,pp
Girard Explosives 1900, 1905 & 1908). See 387-8
Ref 2,p 343; Ref 4,pp 93 & 95; Ref 21,PP Justice Powders(1888). See Ref lb,p 19; Ref
396-7 & 399 2,p 389 & Ref 21,p 394
Goetz Powder. See Ref la,p 349; Ref 2,P 355 Keil Explosive. See Ref lb,p 19 & Ref 2,p 391
& Ref 21,p 400 Kellow & Short Powder(1862). See Ref lb,p 20;
Golovine Explosive(1905). See Ref 21,p 398 Ref 2,p 391; Ref 3,P 262 & Ref 21,P 391
Gomez Powders. See Ref la,p 350; Ref 2,p Kieselbacher Chloratsprengstoff. Same as
356 & Ref 21,p 400 Miedziankit(Ref 8a,p 61)
Gotham Explosive. See Ref la,p 350; Ref 2,p Kinetire Explosive( 1884). See W.Smith JSCI
356 & Ref 21,p 400 6, 2-12(1887). Ref lb,pp 20-1; Ref 2,P 392;
Grafitite or Graphitite( 1896). See Ref 21,p 396 Ref 4,p 186 & Ref 15,p 210
Graham Powder. See Ref la,p 351; Ref 2,p Kirsanow Explosive( 1901). See Ref 3,p 231 &
356; Ref 15,p 212 & Ref 21,p 400 Ref 21,p 397
Green Powder( 1887) .(Poudre verte in Fr). Kiwit. .See Ref 8a,p 54
See Ref lb,p 110; Ref 2,p 784; Ref 15,p 222 & Knaffl powder. See Ref lb,p 21; Ref 2,p 293;
Ref 21,p 396 Ref 3,p 263; Ref 15,p 214 & Ref 21,p 400
Hafenegger Powders(1868). See Ref lb,p 7; (spelled Knaffi)
Ref 2,p 366; Ref 3,p 263 & Ref 21,p 392 K6hler Powder(1857). See Ref lb,p 22; Ref 2,P
Hahn Powders(1867). See Ref lb,p 8; Ref 2,p 393 & Ref 15,P 206
366; Ref 3,p 264 & Ref 15,P 206 Kolbe Explosive. See Ref lb,p 22 & Ref 2,p
Hall(or Will) Powder( 1863). See Ref lb,p 8; 393
Ref 2,p 366 & Ref 21,p 391 Kolowratnik Explosive No 3(1912). See Ref 7,P
Hannan Explosives(1882). See Ref lb,p 9; Ret 325
2,p 368 & Ref 21,p 391 K6pe(Moritz) Explosive(1883). See Ref 15,PP
Harrison Powders(1862). See Ref lb,pp %10; 215-16
Ref 2,p 369 & Ref 21,P 391 Koronit. See Ref 20,p Ger 102
Hart Powder( 1888). See Ref lb,p 10 & Ref 2,p Kraft Dynamite of Bjorkmann. See Ref lb,p
369 23 & Ref 2,P 396
Harvey Explosive. See Ref 2,p 369 & Ref 21,p Landauer Explosives, known also as Landin or
400 Launoy(1891). See Ref lb,p 25; Ref 2,pp
 C 205

402-3 & Ref 21,p 395 Nobel Safety Explosive( 1896). See Ref 2,p 580
Lanolin. See Landauer Explosives & Ref 21,p 396
Lascinski Explosive(1906). See Ref 21,p 399 Noble Powders( 1880). See’ Ref lb,p 57; Ref 2,pp
Launoy. See Landauer Explosives 582-3 & Ref 21,p 393
L.C. Pulver. A Ger Cheddite(Ref 8?,p 56) Nysebastine(1876). See Ref 2,p. 586
Le Mar4chal Powder( 1885). See Ref lb,pp Oliver Powder( 1869). See Ref lb,p 59; Ref 2,p
26-7; Ref 2,p 404; Ref 3,p 266 & Ref 21,p 590 & Ref 21,p 392(spelled Olivier)
394 Oriental Powder. See Ref lb,p 59 & Ref 2,p
Lheure Explosive(1905). See Ref 21,p 398 591
Liardet Explosive( 1893). See Ref 7,p 699 Papier explosible. See Explosive Paper
Lindeman Explosive(1899). See Ref 2,p 408 Parone Explosive. See Ref lb,p 63; Ref 2,p
Lindner Explosive( 1895). See Ref 2,p 409 601 & Ref 15,P 206
Louis Explosives(1905). See Ref 4,p 100 Pattison Explosive( 1880). See Ref lb,p 63;
Mackintosh Powder( 1857). See Ref lb,p 31 Ref 2,p 601 & Ref 21,p 393
Mathews Powder(1905). See Ref 21,p 398 Peck Powder(1905). See Ref 21,p 398
Maurette Powder. See Ref 2,p 420 Pelez(yr ,Peley ?) Explosive Paper. See under
Melland Explosive Paper( 1865). See Ref lb,pp Explosive Papers
36-7; Ref 2,p 436; Ref 3,p 265; Ref 15,p 216 & Pellier Powders( 1882 & 1884). See Ref lb,pp
Ref 21,p 391 65-6; Ref 2,p 603; Ref 15,p 216& Ref 21,p
Melville Powders(1850). See Ref Ib,p 37; Ref 394
2,p 436; Ref 15,p 212& Ref 21,P 391 Perkins Primary Mixtures( 1870). See Ref lb,p
Mendail Explosive. See Bengaline in Vo12,p 66; Ref 2,p 609
B 33-R. It is called Benzalina in Ref 15,p 211 Perlit. See Dr. Roman, NC 3, 161(1932)
Mercurit. See Ref 8a,p 60 Permanit. See Dr. Roman, NC 3, 161(1932)
Michailowski Powder( 1882). See Ref lb,p 39; Pertuiset(or Mundell) Powder(1867). See Ref
Ref 2,p 439 & Ref 21,p 394 lb,p 66; Ref 2,pp 447 & 610; Ref 15,p 206
Miedziankit(Egelit or Kieselbacher Chlorat- & Ref 21,p 392
sprengstoff). See Table 3, Note D under Petrofracteur Explosive. See Ref lb,p 67 &
CHEDDITES Ref 2,p 613
Millbank Explosives. See Ref Ib,p 39& Ref Petrolit. See Ref 8a,p 74
2,p 439 Petry Explosive Card( 1882). See Ref 21,p 394
Mindlite( 1911). See Ref 14,p 360; Ref 15,p Pettinger Primary Mixtures( 1898). See Ref 2,p
210 & Ref 21,p 399 614
Min41ites A, B & C. See Note C, Table 2 Pierrite Explosive. See Ref 8a,p 74
under CHEDDITES P irodialiti. See Pyrodialites of Turpin
Minnensprengstoff. See Table 3 under Pirodialiti senza fiamma. See Ref 21,p 396
CI-IEDDITES Pironome. See Pyronome
Mitchellite. See Ref 8a,p 62 Plastigels. See Table 4 under CHEDDITES
Monnier Powder. See Ref lb,p 41; Ref 2,p 442 Plessit. See Ref 8a,p 76
& Ref 21,p 400 Pohl White Powder. See Ref lb,p 69; Ref 2,p
Mundell Powder. Same compn as Pertuiset 635; Ref 5,p 576 & Ref 15,p 212
Naphthalite. See Ref 8a.p 65 Pollard Powder. See Ref 2,p 635 & Ref 21,p 400
Ni~htingale & Pearson Explosive(1897). See Poudre blanche Cornil. See Cornil White
Ref 2,p 452 & Ref 15,p 212 Powder
Nisser Powders(1865-1870). See Ref lb,pp Poudre v~g~tale. See Castan(Poudre vdg~tale)
43-4; Ref 2,p 452; Ref 3,p 265; Ref 15,p 215 & Prometh4e or Prometheus Explosive(1900).
Ref 21,p 392 See Ref 2,p 382; Ref 3,p 266; Ref 8a,p 77;
Nitrocaillebotte(or Nitrocurds) Explosive of Ref 15,p 231 & Ref 21,p 397
Sj5berg( 1886-7). See Ref lb,pp 47 & 95 and Prussian Fire. See Wigfall Powder
Ref 2,p 493 & 717 Pyrodialites(of Turpin)( 1888-1898). See
Nitrolkrut( 1876). See Ref lb,p 49; Ref 2,p Ref 2,pp 661-4; Ref 3,p 266; Ref 4,p 108 &
560 & Ref 21,p 53 147; Ref 5,p 379 Ref 14,p 360 & Ref 21,p
Nobel Explosive(ca 1880). See Ref lb,p 53 & 396(pirodialiti)(See also Double-Effect
Ref 2,p s77 Powders)
 C 206

Pyrodialites, Flameless. See Pirodialiti senza Sederolite Primary Mixture. See Ref lb,p 93;
fiamma in Ref 21,p 396 Ref 2,p 712 & Ref 21,p 400
Pyronome(1881). See Ref lb,p 74; Ref 2,p Seranine of Horsley. See Ref lb,p 94; Ref 2,P
664 & Ref 21,p 393 713 & Ref 21,p 400
Quinby, Sharps & Gregro Explosive( 1902). See Sharp & Smith Powder( 1866). See Ref lb,p
Ref 21,p 397 94; Ref 2,p 714; Ref 3,p 264; Ref 15,p 215 &
Rack-a-Rock(1881). See Ref lb,p 76; Ref 2,pp Ref 21,p 391
657-8; Ref 3,p 265; Ref 5,p 379; Ref 7,P 135; Siemens Powder(1882). See Ref lb,p 94; Ref
Ref 8a,p 79; Ref 15,pp 231-3 & Ref 21,P 2,P 715; Ref 3,p 264; Ref 15,P 206 & Ref 21,P
393 394
Raibun. See Acldnl Ref U,p 25(in this section) Silberrad Powder( 1911). See Ref 7,PP 675-6
Randites(1892). See Ref 2,p 668 &.Ref 21,p Silesia Powders. See Ref 3,pp lg5-6; Ref 5,PP
395 382-3; Ref 7,p 151; Ref 8a,p 89; Ref 14,P
Rave Explosives(1859). See Ref lb,pp 767; 360; Ref 15,pp 209-10 & Ref 21,p 400
Ref 2,p 669 & Ref 21,p 391 Silesite Powder of Pietrowicz & Sieger(1889).
Rendrock Powder Co Explosives(1881, 1901 & See Ref lb,p 95; Ref 2,P 714& Ref 3,P 81
1904). See Ref 21,pp 393, 397 & 398 Simpson Powder(19@i). See Ref 21,p 398
Reverley Powder(similar to Augendre Powder). Singleton Powder( 1898). See Ref 2,p 717 &
See Ref lb,p 79; Ref 2,p 681; Ref 5,p 377 & Ref 21,p 396
Ref 21,p 400 Sj6berg Explosive( 1886-7). See Nitrocaillebotte
Reynolds Powder. See Ref lb,p 79; Ref 2,p
Slack Powder( 1898). See Ref” 2,p 717 & Ref
681 & Ref 21,p 400
21,p 396
Ricker & Spence Powder( 1862). See Ref lb,p
Sleeper Powder. See Ref lb,p 96 & Ref 2,p
80; Ref 2,p 683; Ref 15,p 214 & Ref 21,p 391
717
Robert Powder( 1873). See Ref lb,p 81 & Ref
Smith Explosive( 1905).. See Ref 21,p 398
2,p 686
“Soci6t6 Universelle d’Explosifs” Explosives
Robertson Powder. See Ref lb,p 82 & Ref 2,p
(1911). See Ref 7,pp 681-2
686
Sodalite Explosive(1897). See Ref 2,p 721 &
Roger Powder( 1870). See Ref lb,p 84; Ref 2,p
Ref 21,p 396
691; Ref 15,p 206 & Ref 21,p 392
Spence Powder. See Ref 2,p 735; Ref 3,p 263 &
Romite( 1882). See Ref lb,p 84; Ref 2,p 691;
Ref 15,p 214( See also Ricke r & Spence
Ref 15,p 206 & Ref 21,p 394
Powder)
Rompe-rota. A Cuban expl similar to Rack-a
Spore Expiosive(1903). See Ref 21,p 397
-Rock. See Ref 15,p 233
Ross & Cairney Explosives(1899). Ref 2,p Sprengel Type Chlorate Explosives. See Ref
693 & Ref 21,p 396(speHed as Roos 3,p 268; Ref 8a,pp 90-1 & Ref 15,P 230
Stanley Explosive(1905). See Ref 2 l,p 398
Rudeloff Plastic Explosives(1906). See Ref
Steele Explosive( 1904). See Ref 2 l,p 398
7 ,p 246
Steelite(1907). See Ref 4,p 148; Ref 5,P
Sanlaville & Laligant Powder( 1880). See Ref
lb,p 87; Ref 2,p 700 & Ref 21,p 393 382; Ref 8a,p 91; Ref 14,P 360 & Ref 15,P
Schindler Powder( 1893). See Ref 2,p 703 & 209
Ref 21,p 395 Stockholm Superfosfat Fabriks AB Explosives
Schlesinger Powder( 1852). See Ref lb,pp (1915). See Ref 7,P 741
Storite Explosives 1893). See Ref 2,p 739 &
89-90 & Ref 2,p 703
Ref 21,p 400
Schnebelin(or Schnebelite) Powder( 1891). See
Ref lb,p 90; Ref 2,p 703 & Ref 21,P 393 Street Explosives or Streetites. Same as
Schnebelin-Boileau Powder(1902). See Ref 2 l,p Cheddites
Stubenrauch’s Explosive( 1896). See Ref 2,p
397
Schfickher Powders( 1890). See Ref lb,pp 90-1 795(as Von Stubenrauch)
Styre Powder( 1900). See Ref 21,p 397
& Ref 2,pp 704-5
Schuler Powder( 1893). See Ref 2,p 705; Ref Teutonite. A modification of Augendre
15,p 212 & Ref 21,p 395 Powder. See Ref 2,pp 74 & 765
Thomas Explosive( 1905). See Ref 21,p 398
Sebomite(1904). See Ref 3,p 266; Ref 4,p
Thorite Powder ( 1895). See Ref 2,p 766 & Ref
148; Ref 8a,p 88; Ref 14,p 360 & Ref 21,p
21,p 395
398
 C 207

Thunder Powder. See Ref lb,p 103 & Ref 2,p & Ref 21,p 394
767 White Powder. See Augendre Powder
Tzobach Primary Mixture(1890). See Ref 2,p Wigfall Powder or Prussian Fire( Feu
776 prussien in Fr). See Ref 2,p 809 & Ref 21,p
Tschirner Explosive( 1880). See Ref. lb,p 105; 391
Ref 2,p 777; Ref 7,pp 693-4; Ref 15,p 222 & Wilhelmit. See Ref 8a,p 103
Ref 21,p 393 William Powder. See Ref lb,p 118 & Ref 2,p
Turpin Explosives Containing Chlorates. See 810
Boritines, Double Effect Powders, Duplexite, Winiwarter Primary Mixture(1852 & 1853). See
Fluorine, Pyrodyalites and “un-named” expls Ref lb,p 1“18 & Ref 2,p 810
listed in Ref lb,p 108 Zaliwsky Powder. See Ref lb,p 120-1 & Ref
Un-named-.chlorate explosives of Turpin. See 2,p 814 .
Ref lb,p 108 Some chlorate mixts which bear no names
US Naval Friction Fuse Composition are listed under Addnl Refs. , which follow
(obsolete)...See Ref 2,p 779
“V4g4tale” Powder of Castan( 1884). See Properties 01 Chlorate Explosives. In general,
Castan(Poudre vdg~tale) expls based on chlorares are very powerful
Velterine C or Welterine C(1893-1897). See and brisant, but are very sensitive to friction
Ref 2,p 783 & Ref 7,p 35 and impact. Coating of particles of chlorates
Venghldffer Powder( 1889). See Ref 21,p 395 with substances such as castor ,oiI, rosin,
Verg4 Explosive( 1903). See Ref 2 l,p 397 paraffin, tar, aromatic nitrocompds, crude
Verte(Poudre). See Green Powder rubber, vaselin, pertoleum, plastic materials,
Victorite( 1887). See Ref lb,p 110; Ref 2,p diminish considerably the sensitiveness but
785; Ref 7,p 323 & Ref 15,p 222 not sufficiently to make these expls suitable
Vigorine of Bjorkmann( 1875), also called for loading artillery shells(See CHEDDITES)
(incorrectly accdg to Salvati) Vigorite. See The chlorate expls are more sensitive
Ref 2,p 785 and Ref 21,pp 387 & 392 than those contg perchlorates, and expls contg
Vigorite of California Vigorite Powder Co. See Na chlorate are more sensitive than those with
Ref lb,p 111 & Ref 2,p 786 K chlorate. Expls contg K or Na chlorate
Yigorite of Hamilton Powder Co. See Ref lb,pp shouId not be mixed with Arnm salts because,
110-1 1; Ref 2,p 786 & Ref 8a,pp 100-1 in this case, double decomp takes place
Vigorite of Nordenfeldt. See Ref 3,p 362 with rhe formation of Amm chlorate which can
Von Brank’s Powders. See Brank’s Powders explode spontaneously. It also is advisable not
in Vol 2 of Encyclopedia or in Ref 2,p 790 to use eirher PA or. TNCrs in chlorate expls,
Von Stubenrauch’s Explosives. See Stuben- because such mixts are very sensitive(Ref 7,p
rauch’s Explosives 383). These precautions were not alwaYs
Von Wendland’s Explosive. See Wendland’s followed
Explosive (See also under individual chlorate expls, such
Vril Explosives 1889). See Ref Ib,p 113; Ref as CHEDDITES)
2,p 797; Ref 3,p 264; Ref 4,p 81 & Ref 2 l,p Uses of Chlorate Explosives. Most chlorate
395 expIs have been used for industrial purposes,
Vulcalne Explosive(1893). See Ref 2,p 797 but during WWI & WWII some were used by the
Vulcan Powder(Poudre vulcain in Fr). See French, Russians, Italians, Japanese and
Ref lb,p 113 & Ref 2,p 797 Germ ans for loading mines, torpedoes, hand
Vulcanite of Moritz & K6ppel(Austria). See grenades & depth charge s(but not in artillery
Ref lb,p 114 & Ref 2,p 798 shells). Many expls contg chlorate have been
Wahlenberg Explosives 1876). See Ref lb,p used in primers and detonators
115; Ref 2,p 800; Ref 15,p 230(spelled (See also under individual expls, such as
Walenberg) & Ref 21,p 392 CHEDDITES)
Ward & Gregory Powder, See Ref 2 l,p 400 Re/s: la)CundiH(1889) in MP 5(1892) lb)
Ward & Gregory Primary Mixture. See Ref 2,p Cundill( 1889) in MP 6(1893) 2)Daniel(1902),
802 various pages 3)Gody( 1907), 262-70 4)
Weber Powder. See Ref 2,p 803 Escales, Chloratspr( 1910), 76-1,00 (List of
Wendland’s Explosive( 1886). See Ref 2,p 796 patents from 1849 to 1909); 143-6 (Compns &
 C 208

props of chlorate expls used ca 191O) 5) & perchlorate expls) H)P. B jdrkman,
Marshall 1 (1917), 377-82 6)Marshall 2(1917), Tek.TidUpplCKemi 64; 41-4( 1934) & CA 28,
759 7)Colver(1918), 135,159,167,246-7, 6311-12 (1934 )( Claims that expls prepd by
278,323,325,351,673,675-6,681-2,693-6,699 & impregnating porous K chlorate briquets or
741 8) Barnett( 19 19), 106-13 8a)Marshall, grains with liq hydrocarbons are less sen-
Dict(1920), various papes 9)Na o~m, NG sitive to friction than ordinary K chlorate
(1928), 427-30 10)Vennin, Bur!ot & L~corch~ expls) I)G. von Feilitzen, Ibid(Claims that
(1932), 537-44 ll)Marshall 3(1932), 111-13 B’s expls are sensitive to friction; -several
12)Stettbacher( 1933), 309-15 13)pepin accidents with these expls are cited) J)
Lehalleur(1935)t 344-50 13a)I.F.Blinov, I. G. Farbenind AG, USP 2000414(1934) & CA
“Khloratnyiye i Perkhloratnyiye Vztyvchatyiye 29, 4180( 193 5)(Claims that incorporation of
Veshchestva’ ‘(Chlorate and Perchlorate Amm chlorate, up to 20%, in Na nitrate expls
Explosives), Oborongiz, MOSCOW(1941) 14) increases their brisance without increasing
Davis( 1943), 357-63 15)pdrez Ara(1945) their sensitivity to friction) K) I. F. Blinov,
199-261, 222 & 230-32 16)Vivas, Feigenspan ZhPriklKhim 8, 52-5( 1935) & CA 29, 7077
& Ladreda Z( 1946), 347 & 349 17)Stettbacher (193 5) [ Impact test values were detd for the
(1948), 90-1 18)Belgrano(1952), 179-81 following types of chlorate expls: a)92ps of
19)Stettbacher( 1952), 117-19 20)PATR 2510 K chlorate(grain size O. 15mm) mixed with 8ps
(PB 161270)( 1958),PP Ger 3,23,28,32,69,136 of Iiq desensitizer(such as kerosene, xylene,
& 154 21) Giua, Trattato 6(1959, 390-400 glycerin, castor oil, MNT, aniline or benzene)
22)1.Huhtanen, Explosivst 1960, 189-94 and b)K chlorate 85ps mixed with 15ps of a
(Chlorate expls used in Finland) 23)F.A. solid or semi-solid desensitizer(such as rosin,
Warren et alJ*Chlorates and Perchlorates., MNN, petroleum bottoms, naphthalene, paraffin
Their Manufacture, Properties and Uses”, or petrolatum). Results of tests have shown
NAVORD Rept 7147(Vol 1)(1960), 195-208 that with the liquids$ the sensitivity depends
24)Ibid, Vol 2( 1960) (Conf)(not used as a mainly on their them structure(aromatic
source of info) compds showed the highest desensitizing
Addnl Re/s: A)Sprengstoff AG Carbonit,GerP props), while the viscosity was of secondary
307880( 1917)( not found in CA or in JSCI) importance. As to the solid- or semi-solid
(Expls prepd by fusing chlorates with urea or ingredients, their desensitizing props depend
other substances capable of forming easily not only on their compn, but also on the
fusable masses) B)J .Baumann, ChemZtg plasticity) L)L.S.Beyers, USP 2079105(1937)
44, 474(1920) & CA 14, 2712( 1920) (Chlorate & CA 31, 4500(1937) [Blasting expls contg
expls contg dicyandiamide) C)E .Wolcott, 66-73Ps of a mixt of alkali chlorate & alkali
USP 1355203(1920) & CA 15, 177(1921) nitrate together with 17-20ps of Iiq DNT(fr p
(Desensitized K chlorate suitable for use 3-15°) and 10-14% of a 20-60 mesh woodmealj
in expl compns can be prepd by crystn from art M)L.S.Beyers, USP 2083 143(1937) & CA 31,
aq soln of chlorate and sulfonated derivs of 5583(1937) [An expl suitable for blasting: K
California pertoleum) D) B. Miihlefeld, SS 16, chlorate 38-41, Na nitrate 19-23, shredded
113-15(1921) & CA 16, 496(1922 )( Description wood 13-14, liq DNT(frp -5-+ 15°) 23.5-27.5 &
of chlorate expls used in Germany for blasting NC(N> 12%) 0.5-2.5%. Method of prepn is
rocks of medium hardness and in potash, rock described] N)I.F. Blinov, Kalii(Russia),
salt & iron ore mining) E) E. Spitalsky & E. 1937, No 10, 19-31 & CA 33, 3155-6(1939)
Krause, SS 20, 103-7, 119-23 & 133-5(1925) (Compn & props of some Rus chlorate expls
& CA 20, 1141(1926)(Description of chlorate of weak & medium strength used in open or
expls used in Russia) F) A. C. Scott & Mexco, underground work) O)C.O.Davis, USP
Ltd, BtitP 248089( 1926) & CA 21, 652(1927) 2190703(1940) & CA 34, 4270-l(1940)(Expls
(Crysts of O-carrying substs, such as K prepd by dispersing a solid “O-accepting”
chlorate are coated with synthetic resin such ingredient, such as Al, ferro-Si, S, sugar,
as may be formed from a phenol, a phenol & nitrocompd, etc with a chlorate or perchlorate
formaldehyde, or from urea or thiourea. Other dispersed in anhydrous ammonia) P )D.C.
ingredients such as MNN, DNT, a perchlorate McMeans, USP 2109049(1938) & CA 32, 3156
or woodmeal may be added) G)Dr. Roman, NC ( 1938) [ Granular chlorate expl suitable for
3, 161-3 (1932 )( Compn & props of some chlorate underground work is. prepd by mixing KC103
 C 209

35, a ‘ ‘hot mixture” 20(obtained by heating are given by Fedoroff et al in PATR 2510
12ps of liq DNT, 6ps of toluene & 2ps of ( ‘1958),P Ger 28. See also A.Haid & H.Selle, SS
petrolatum with a small runt of nitric acid 251-2(1929) & Pepin Lehalleur( ,1935), 347
until disappearance of N oxides fumes),
sugar 35 & sawdust 10%] Q)E.Lorenzini, Chlorate-Rivalit. A Ger expl introduced during
BritP 535971(1941) & CA 36, 1496(1942) WWI: K chlorate 88.5 & paraffin 11.5%
[ Expl compns prepd by mixing solns(in w Re/: MarshaH, Dict(1920), 82
or in other suitable solvents) of inorg or org
chlorates and/or perchlorates with binding Chloratzit. A Ger expl contg K chlorate &
substances, such as dextrin, starch or gum perchlorate together with aromatic nitrocompds,
arabic, followed by incorporation of com- resins and carbohydrates. Cooling agents were
bustibles such as cellulose, coal dust, sulfur, incorporated for mixts intended for use in coal
etc, which were previously stirred with w, The mines, and the name was changed to Kohlen- or
resulting slurry is then concentrated into a Wetter- Chloratzit
paste and mixed with a stabilizing oily subst, Re/: Marshall, Dict(1920), 21
such as vaselin, paraffin, or castor oil) R)J.
B~llwiHer, FrP 862323(1941) & CA 42; 9179-80 Chloratodimercuriacetaldehyde or Chlorat-
(1948) [ Expls obtained by mixing Amm chlorate odimercuraldehyde, OHC. C(:Hg).HgCIOa; mw
(nitrate or perchlorate) with naphthalene, 625.66, COI, lustrous prisms, exceedingly expl
paraffin, lubricating oil, etc can be exploded even when covered with w; was obtd by adding
in a closed space by a compn such as thermite) alc acetaldehyde to a soln of mercuric oxide
S)W.R.Tomlinson, Jr, PATR 1230(1943) in aq HC103. It explodes violently just by
(Investigation of two chlorare expls of the shaking even under water
Universal Powder Co showed that these Re/s: l)Beil 3, 606( Under Oxydimercuriacetal-
expls offered no promise for use in military dehyd) 2)K.A.Hofmann, Ber 38, 2000(1905)
ammo or in demolition work) T)A.J.Phillips,
PATR 1277( 1943 )(Study of Na chlorate expls Chlorototrimercuriacetaldehyde or Chlorato-
of Kiernan & Bowen showed that these expls trimercuraldehyde, Hg
offered no promise for use in military ammo OHC.<’ ~o).Hgc,03;
or in demolition work) U)Anon, “Handbook ‘>Hg’ ‘
of Japanese Explosive Ordnance”, OpNav mw 742.25; wh pdr, explodes on contact with a
30-3M( 1945), 25-32(Compns of Jap chlorate flame or coned sulfuric acid; can be prepd by
expls: Bakufun, Ennayaku, Entoyaku passing acetylene into an aq soln of mercuric
& Raibun) V)G.C.Tibbits et al, pB Rept chlorate “or into a mixt of mercuric nitrate and
50394( 1946),p 91( Japanese used during WWII, Na chlorate. It is S1 less expl than the
quite extensively, mixts contg chlorates or dimercuric compd above
perchlorates, both for industrial and military Wohl er & Matter(Ref 3) give the following
purposes, such as in blasting, demolition work, expl props: Expln Ternp 130° (in 20 secs)(See
mines and depth charges ) W)L.Mddard, Mp also Ref 4) and Lead Block Expansion at d
35, 210-14 & 218( 1950)(Chlorate expls developed 2.995 15.3cc vs 25.6 at d 3.368 for MF
after WWII by the Commission des Substances Re/s: l)Beil 3, 607{ Under Tris- [h ydcoxymercuri ]
Explosives) X)S.Custodero, ItalP 522944 -acetaldehyd } 2) K. A. Hofmann, Ber 38, 2001
(1955) & CA 53, 3698( 1959) (ExP1s prepd by ( 1905) 3) L.W6hler & O. Matter, SS 2, 204-5 &
incorporating an oxidizer, such as a chlorate 247(1907) 4)Davis(1943), 411
or a perchlorate into a liquid polymer, which
is then solidified by addn of a suitable Chloric Acid, HC103; mw 84.47, exists only in
catalyst) Y)I.Huhtanen, Explosivst 1960, aq solns, the highest concn of which corresponds
189-94(Same chlorate expls used in Finland) to the bepta- hydrate, HC103.7H20;” mw 210.58.
Its solns(up to 40%), are coIorIess, frp <-20°,
Chloratit. A type of Austrian and Ger chlotate bp dec 40°, d 1.282 at 14.2°; toxic rating is
expl, consisting of Na or K chlorate & hydro- given in Sax(Ref 7). Its usual method of prepn is
carbons in a variety of compns, which was to treat an aq suspension of Ba chlorate with
sanctioned for blasting operations during and an equiv amt of dil H2S04; after filtering the
after WWI. Some chloratit compns & their props BSS04, the COI filtrate is coned in vacuo at
 C 210

1O-2O” over coned H2~4 to a d of 1.26. This or org cxm,pds, sometimes vioIently(Ref 4).
corresponds to a 40% soIn; attempts to prep Wood, paper & similar ,materids decomp the
stronger soins always resulted in decompn acid at once, very often with spontaneous
Solns up to 30% strength are fairly stable combustion or even a mild expfosion.
when stored in the cold, away from light, and The salts of chloric acid, called Chlorates
provided org matter is absent. Coned solns of (qv), are important compds in the expl, proplnt &
HC103 are dangerous to store because on pyrotechnic industries
standing they form chIorine dioxide, U02, Re/s: l)Mellor 2(1922), 269 & 305 2) Gmelin,
one of the most powerful oxidg agents. When aq Syst Nr 6(1927), 307 3)Mellor( 1939), 515
solns are warmed, chlorine & C102 may evolve 4) V.Majer, Chemie(Prague) 3, 90-1( 194$) & CA
depending upon the concn 46, 2805( 1952)( Explosion produced by
Cldoric acid is strongly ionized in w and in HC103) >)Kirk & Orhmer 3(1949), 707 6)
some org SOIVS. It is a strong oxidg agent Ullmann 5( 1954), 525-6 7)S?X(1957), 461
reacting with reducing compns. such as metals
 TABLE IX
Types Grain Dimensions,Weightsof Charges and Other Data for Propellants Used in US Army Artillery Ammunition (Except Rockets)
(lnformation for this table was supplied by Russell L. Trask and J. F. W. Pflueger of Picatinny Arsenal)

Mod*l, Type ad Woigftt

Of ChOmbw Difference: Typo, Modol Velocity of
C?eltulatiee 01 PfOpdlanl Pr**sw*, psi GrainDimensions in inches Ratio Ratio NuiMf!I Type of encl Weight of Proiectilq Dcsienation of Weapon,
PIepewexf Cbefge Kew- sew) L D d w W* 4 % L/D D/d k Ammunition Pr+etilcc lb, Ips C.iib.r and MOd.f
la Omcos

LMR 700S;(SB w 1.29 55300 0.0845 0.05-42 0.0113 0.0215 - - - L36 4.80 - FA Ctge, Ball, M55A1 3380 Gun, 20mm, bt39
DNT coatiogh SP (0.217)

Ball, S’C870 1.38 520CQ Granuhon (lWICMt retained on IJS Sievesk 0.12C% on so lk 0.13 On 187.93 cm 2042.08
—. on 25; 48.3E On 3& FA Ctge, Ltall, bt.55A2 33W Gtm,20mnl, bj39
0.67 on 35 arid 0.49% On NO 40 (0.217)

NZ(DBk SP 4.30 30000 0.2405 0.0617 0.LW73 0.0272 3.$X3 8.45 FA Pratt, M55A1 (1.34) 2600 (An, 37mm,.fJl A2 k ,M9

Ml; (SBW DXTL SP 10.48 40000 0.2770 0.1221 0.0143 0.0210 0.0186 0.0198 2.27 &54 12.12 FA AP, M87A1 (1.96) 2870 Gun, 40mm, Ml

Ml&(SBk SP 13.95 5300 0.1351 0.0492 0.0134 0.0179 2.75 3.67 - FA flE, ht306Al (2.75) 1200 Rec R, 57mm, Mi8 &
M18A1

Ma (DBk Sheet 0.%4 1“. 1.X0,004. - MA HE, M49A2 (3.07) hiOnW, h~, M2abt19
(FOW kfiCMMttS)

M% (DBh Discs in 0.091 0.0031 0.0345 - MA HE, .M49A2 (3.07) fhta, 60mm, M2a ML9
Ig.itien Ctge M5A1

MIU (SBk kIP 32.97 6800 0.4587 0. 1%3 0.0203 0.0335 0.0341 0.033s 2.34 9.67 -1.78 FA NE, M309AI (14.40) 990 Rec R, 75mm, M20

Ml; (SB w DNT)SP 17.03 33500 0.2828 0.0476 0.0184 0.0146 5.94 2.59 - FA HE, M48 (14.70) 1500 GUI, 75mm, M1897

Ml; (SB w DNTk 8P 5.82(Z1) S400 0.2798 0.0S67 0.0188 0.0189 4.93 3.02 - SF HE, .M48 (14.70) 700 t{ow, 75mm, MlAl&h13
7.4NZ2) 6200 810
9.66(Z3) 10300 950
14.55(24) 2SM0 1250

Mlfi(TBk W’ >7.84 39500 0.6860 0.302kI 0.028 0.0559 0.0535 0.0547 2.27 10.89 4.39 FA AP-T, T166E2 (14.60) 271Xl Gun, 76mm, b+l, MlA2
& MIAIC

bk% (DBk she= 1.87 4980 2.223 - 0.244 1,437 Distace becwpetforatims 1.438 in; thickness Ofsheeto.oo80i~ MA HE, M56(10.92&lL40) 573 Mortar. 81mm, Ml&M29
Max variation in thickness 0.0014 in
(FOIS knscenems)

M% (DBk Discs in 0.274 0.0094 0.0589 - MA HE, M56 (10.92& 11.40) 573 kt.rmr, 81mm, Ml 6ibf29
3@imI Ctges M3
&kkd O.1%
 TABLE IX (cent)
Model, Type and Weight of Chamber Difference: Type, Model Volocity of
Granulation of Propellant Pressure, psi Grain Dimensions in inches Ratio Ratio (~. Wl) x 100 Type of and Weight of Projectile Designation of Weapon,
Propellant Charge (Copper gage) L D d w Wo Wi wa L/D D/d w. Ammunition Projectile,lbs fps Caliber and Model

1“ *“”..,

M; (D13); Discs 2.98 0.012 0.061 MA HE, M362 (9.42) fllmn Mortar, hQ9
(Eight increments) m
0.W>5

Mz(cff} r7isc.
i,) 0.262 0.0114 f2.0619 MA HE, M3C2 (9.42) 81mm Mortar, hf29
Ignition Ctge M(X

M(X (58 w C\ T); 116.73 36300 0.6452 0.2715 0.0240 - 0.0514 0.0486 0.0s00 2.38 5.60 11.36 FA HE, M71 (23.40) 2700 Gun, SOmm, Ml, MlAl,
(Sulfh VP M2 & M3

141, s8 44000 1.1437 0.4733 0.0533 - 0.0802 0.076S 0.0784 2.42 4.72 8.23R FA AP-T, M31LIA1 (24.10) 3000 Gun, 90mm, M36

8- S>(Z1) 6600 0.249 0.0478 0.0192 0.0143 - 5.21 2.49 SF HE, Ml (33.00) 650 How, 105mm, M2A2 &
9.9&72) 8200 710 M4A1
\!l; (SDw D> Th\lP 12.s1 (73) .9200 0.3541 0.14(S 0.0140 - 0.0255 0.0269 0.0262 2.42 10.47 -5.34 782
16.31(Z4) IIIX)O 875
22.0N73) 14350 1020
n
tu
30.85(76)
45.25(Z7)
198W
31OO+J
1235
1s>0 z
122.0> 7100 0.4517 0,1944 0.0204 - 0.0330 0.0342 0.0336 2.32 9.>3 -3.57 FA HEP-T, M326 (2j,50) 1265 Rec R, 105mm, M27
& f.427Al

129. CO B6W 0.5130 0.2217 0.0232 - 0.0373 0,0387 0.03s2 2.32 9.56 -3.68 FA HEAT, M344 (17.55) 16s0 Rcc R, 106mm, M40

W (D13k %ect 6.84 Ilsc$l Sheer thickness 0.026 i“; LenEch of sides 2.6>2 in; Uidth of sides 2.6W in; .4verage 2.671 im Diamerer of MA HE, M3A1 (25.50) 809 Mortar, 4.2 in, M2
(Four increments) perforation 1.36 in

M?, (DBh Discs in 0.274 30 information at our disposal almut dimensions of discs MA HE, M3A1 (25.50) S09 M.xtac, 4.2 in, M2
IgnitiOn Ctge \i2

In p.suds

W (Tif); MP 29.43 44800 1.545 0.642 0.063 - 0.118 0.110 0.114 2.41 10.19 7.02 SeP A AP-T (50.85) 3500 Gun, 120mm, M58

.M6 (SB w DXT).\IY 30.86 38$00 0.6887 0.3067 0.0287 - 0.05s6 0.0547 0.0S52 2.25 10.69 1.63 SLA HE, M101 (95) 2RO0 (An, 155mm, M2A1
& !442
 TABLE IX (cent)

htad.1,Typa end W.i@ of Chamber Diff.mncm Type, kkdcl v*lOcity .1

Ganulotiam of Prop.llent Pmssum, psi Grain Dimmsions in inch-s Ratio Ratio (We-w;)xwl) Typ* of and Weight of Pr0~9ctil*, D.slgnation of WwpOII
Pr.+lanf charge (*W 9.*) L D d w we Wi w. L/D D/d we — Ammunition Pro@tile, Ibs fps COlibar and fkd.i

1. pounds

Ml; (SB W DNT, 4.15(Z3) 55@l 0.4033 0.1763 0.0143 – 0.0332 0.0336 0.0334 2.29 12.33 -1.20 SLA HE, M107(95) 880 How, 15jmm, M2
Sulfi .MP 5.32fz4) 7000 1020
7.05(Z5) 10250 1220
9.82(Z6) 17500 1520
13.2qz7) 31000 1850

MI$ (SB W DXTk MP 20.58(ZI) l15cm 0.s614 0.4187 0.M25 - 0.0736 0.0720 0.0728 2.30 9.84 2.20 SLA HE, M437 (147.75) 1675 Gun, 175mm, Ml13
37.75(Z2) 176U0 2310
55. 56(Z3) 436(W 31X20

?46 (SB w DXTk MP 80.&i9(reJ) 29300 1.1520 0.4815 0.0487 - 0.0851 0.0826 0.0839 2.39 9.89 2.98 SLA HE, M103 (240) 2600 Gun, 8 in, Ml
92.27(nor) 37600 2850

Mk (SB w DNTh W 16.62(Z5) 12s00 0.>574 0.2403 0.0249 - 0.0425 0.0402 0.0414 2.32 9.65 5.56 SLA HE, MI06 (2CO) 13wl HOW, 8in, .W2
21.84(Z6) 19800 1640
2a05(z7) 32CCX2 1950

M (SB wDNT)i F@ 43.6.3(Z1) 104s0 0.9s50 0.4154 0.0426 - 0.0726 0.0711 0.0791 2.30 9.77 2.08 SL A HE, f.il14 (360) lSW How, 240mm, Ml
54.01(Z2) 15100 1740
6J5.59(Z3) 22900 2020
79. n(z4) 34000 2350

M (SB w DNTk .MP H3&4fred) lWOO 1.3093 0.5336 0.0505 - 0.1023 0.0888 0.0956 2.45 10.57 14.12 SLA HE, M350 (800) 1?m Gun, 2fDmm, !466
140.o(mr) 31700 2050

AbbNviotioms Uwd in Tabfo IX ammo - ammunition AP - Annoepicrcin& AP. I - Amoppiercingincen.diar~ AP-T - Armorpiercing-traceG Cal - CalibeG Ctge - Cartridge; D - Diameter of proplnt graiIv d - Diameter
of grain perfotaric. o% (DE) - Doublebasc p,OpbU; FA - Fixed ammo; Pp. - Feet per second (0.3048 m/sech HE - liigb.explosiv~ HEAT - Hip,hexplosiv&antitti, HEP-T - High-e~losivepIaxi& ttacff, ffw -

HQWit?.w $n - inch(25.4mmh L - Length of propim maim M - +ACM3clor MO iif i cation; m - meter (3.2808 feet); MA - Mortar amm~ MP - Multiperforatcd (7)grai~ mol- noma~ Pratt - Practice proplnt - prOpeiIant;
psi - pounds per square inch (0.07031 k~sq cmk Rac R - Recoilfess rifle; rod - reduc l +, 5A - Small arnq SB - Singl*base proplnq Sap A - Separated amm~ SFA - Smni.fixed amm, Sf.A -. ~arate loading amm~
SP - SingIe.perforated grain; SuIf - sulfated T - Experimental M (TB) - Triplebase proplnu W - Web rhick”ess of w pmplnt grain, w - with; Wa - Average web of b4P proplnt grai~ Wi - Inner web of MP proplnt grain;
we - Outer web of MP pmplnt graiq Z - Zone

Note: ~mpesitions of MI, $!2, M5, $f6, ,i18, M9, M1O, M17 & \i26 me given in Tables V, VI, & VII, un~er CAY4CE4 PROPELL AhT
 C 215

SUPPLEMENT
TO THE
LIST OF THE BOOKS ON EXPLOSIVES AND
RELATED ITEMS GIVEN IN VOL 1, p A676

1 )P. F. Chalon, “Les Explosifs Modernes, ” 22)H. E. Watts, c{The Law Relating to Explo-
C. B6ranger, Paris(1911) 2)W. R. Quinan, sives,” Griffin, London(1954) 23)Ya. B.
{‘High Explosive s,” Critchley Parker, Zel’dovich & A. S. Kompaneets, t ‘Teoriya
London(1912) 3)A.Marshall, “Dictionary Detonatsii” (Theory of Detonation), GosIzdat-
of Explosives, ” Churchill, London(1920) Tekh-TeorLit, Moscow(1955) 24) E.Ott,
4)M. Giua, ‘fLe Polvere Senza Fume, ” c‘Cellulose and Cellulose Derivative s,”
Subalpina, Torino(1930) 5)G. D. Clift & Interscience, NY, Vol V, Parts l,2& 3(1954-
B. T. Fedoroff, “A Manual for Explosives Lab- 1955) 25) T. Urbarfski, “Teoria Nitrowania”
oratories, ” Lefax, Philadelphia, Pa, Vols (Theory of Nitration), P aAstwoweWydNaukowe,
1-4(1942-1944) 6) A. L. Olsen & J. W. Greene, Warsaw(1955) 26) E. M. M. Gonz61ez, c‘Ex-
“Laboratory Manual of Explosive Chemistry, ” plosives, ” Ediciones Ejdrcito, Madrid(1955)
Wiley, NY(1943) 7)P. F. Bubnov, 27)A. J. Zaehringer, ‘ ‘Solid Propellant Rock-
‘ CInitsiiruyoushchiiye Vzryvchatyiye Vesh- ets, ” First Stage, AmRocketCo, Wyandotte,
chestva, ” (Initiating Explosives), Cboronguiz, Mich(1955) 28)A. A. Sergeev, “Rules for
MOSCOW(1946) 8) C. Dor4e, t ‘The Methods Safety Measures, when Working with Explo-
of Cellulose Chemistry, ” Chapmm & Hall, sives, ” Ugletekhizdat, Moscow(1955) (in RUS)
London(1947) 9) F. Weichelt, “Handbuch 29) F. D. Miles, “Cellulose Nitrate, ” Oliver
der gewerblichen Sprengtechnik, ” Marhold, & Boyd, London(1955) 30) C. Bignotti,
Halle-Saale(1949) 10)T. Tharaldsen, “Nitrocellulose,” Cya, Firenze(1956)
“Eksplosivstoff er,” Dreyers Vorlag, Oslo 30a)J. Cottenet, “Les Explosifs au Service
(1950) 1 l) A. Izzo, C‘Pirotecnia e Fuochi de l‘Agriculture, ” Maison Rusti que, Paris
Artificial,” Hoepli Milano(1950) 12) (1956) 31)K.K. Andreev, “Vzryv i
K. Fabel, C{Nitrocellulose, ” F. Enke Verlag, Vzryvchatyiye Veschchestva” (Explosion &
Stuttgart(1950) 13) J. M. Jimthez, “Explo- Explosives), VoyenIzdat, Moscow(1956)
sives, “ Ediciones Ej~rcito, Madrid(1951) 32)K.K. Andrej ew(Andreev), c‘Sprengstoffe, ”
14) A. Kenneweg, { ‘Ueber den Umgang mit Verlag Mini sterium fiir N ationale Verteidigung,
Nitrocellulose, ” Verlagsgesellschaft, R. Berlin(1957) 33)K.K.Andteev, “Termi-
Muller, Koln-Braunsfeld( 195 2) 15) J. Taylor, cheskoye Razlozheniye i Goreniye Vzryv-
~’Detonation in Condensed Explosive s,” chatykh Veshchestv” (Thermal Decompo-
Clarendon Press, Oxford, Englmd(1952) sition and Burning of Explosives), Go senergo-
16)A. Izzo, “Manuale del Minatore Esplosi- izdat, MOSCOW(1957) 34)N. E. Yaremenko
vista, ” Hoepli, Milano(1953) 17)K.K. & B. Ya.Svetlov, “Teoriya i Tekhnologiya
Andreev, { ‘Vzryv” (Explosion), GosIzdat- Promyshlenykh Vzryvchatykh Veshchestv”
Tekh-TeorLit, Moscow(1953) 18)A.A. (Theory & Technology of Industrial Explo-
Shidlovskii, “Osnovy Pirotekhniki” (Funda- sives), Promstroyizdat, MOSCOW(195 7)
mentals of Pyrotechnics), GosIzdatOboron- 34a)S. F. Vaskovskii,. “Prakticheskoye
Prom, Moscow(1954) 19)G. I. Pokrovskii, Rukovodstvo po Obrashchenyou s Vzryvchatymi
“Vzryv” (Explosion), VoyenIzdMini stObor, Materialami” (Instruction for Handling Explo-
MOSCOW(1954) 20)D. .%nolenski, “Teoria sive Material s,” Gosgeoltekhizdat, Moscow
Materialow Wybucho wych” (Theory of EXPIO- (1957) 35)A. J .Zaeringer, “Solid Propel-
sive Substances), WydMinistOboronyN =odo wej, lant Rockets, ” 2nd Stage, AmRocketCo,
Warsaw(1954) 21)G.Castellfrmchi & p. Wyandotte, Mich(1958) 35a)F. A. Warren,
Malatesta, “Lezioni di Chimi ca di Guerra, ” “Rocket Propellants, ” Reinhold, NY(1958)
Ed Studium, Roma, Part 1 ‘( Esplosivi, ” Pt2 36)T. Urbatfski, “Chemie a Technologies
“Aggressive Chimice” (1954), 640 PP V~bu5in, ” (Chemistry & Technology of
 C 216

Explosives), StiitnfNakladelstvlTechnik6
Lit eratury, Praha, lDil(l 958) (Translated
from Polish) 37)M. Giua & M. L. Marchino,
“Esplosivi, ” pp 1 to 497 in “Trattato di
Chimica Industrial,” UTET, Torino, vol
VI(1959) 38)F. A. Baum, K. P. Stanyukovich
& B. I. Shekht er, ‘q Fizika Vzryva” (Physics
of Explosion), GosIzdFiz-TekhLit, Moscow
(1959) 39) J. Honyman, “Recent Advances
in the Chemistry of Cellulose and Starch, ”
bterscience, NY(1959) 40)Ye.Yu.0rlova,
<‘Khimia y Tekhnologi a Brizantnykh Vzryv-
chatykh Veshchestv, ” GosNauchTekhIzdat,
Moscow(1960) (2 parts) (English translation
under the title ‘ ‘The Chemistry and Tech-
nology of High Explosives, ” was prepd in
linotyped form by Technical Documents
Li ai son Office, Wright-Patterson Air Force
Base, Ohio, MCL-844/H2, June 1961) 41)
Anon, t ‘Analytical Methods for Powders and
Explosives, ” AB Bofors, Nobelkrut, Sweden
(1960) 42)K.K. Andreev & A. F. Beliaev,
“Teoriya Vzryvchatykh Veshchestv” (Theory
of Explosives), Go sNauchTekhIzdat, Moscow
(1960) 43)H; Ellern, ‘ ‘Modem P yrot eth-
nics, ” ChemPublgCo, NY(1961) 44)R.P.
Antonelli, ‘~Encyclopedia of Explosive s,”
OTIA, Ordnance Liaison Group, Durham, NC
(A compilation of principal expls, their
characteristics, processes of manuf & uses)
45)T.Urba6ski, c‘Chemistry and Technology
of Explosives, “ Pergamon Press, NY, Vols
1- 3(1962) (Translated from Polish)
 C 217

A cumulative alphabetical listing of items discussed in Vols 1 & 2, which may not
necessairly begin with letters A, B & C, but which may represent alternate names of
items or compounds already listed alphabetically in the text. NOTE: AH page -numbaws
preceded by alphabet letter A refer to Vol 1; pages preceded by letters B &-C are ~und
in Vol 2,

Abbreviations, Code Names & Symbols American Ammonium Nitrate Dynamites

Vol 1, Abbr 1-65; Vol 2, IX A355 (table)
Abbreviations for Books, Periodicals, etc, American Ammonium Nitrate Gelatin
Vol 1, Abbr 66-76; Vol 2, XI Dynamites A368 (table)
Acetazidine or Azidine A24-R, A627-R 4-Amidino-l-nitrosamidino-tetrazene. See
Acetoacetyldipheny lamine, Same as Guanylnitrosaminoguany l-tetrazene or
N, N-Diphenylacetamide Tetracene under GuanyIaminoguanyI-
Acrylic Aldehyde or Acrolein A96-L tetrazene and Derivatives
Action of Solvents on Cellulose Nitrate. Amidocarbonic Acid. See Carbamic Acid
See Cellulose Nitrate, Action of C40-L
Solvents Cl 15-R Aminobutane. Same as Butylamine B377-L
Active Oxygen A101-L & A515-L Amino formic Acid. See Carbamic Acid
Actual Nitric as Nitric Acid A89-L & A90-L C40-L
Actual Sulfuric as Nitric Acid AX-R AmmonaImatrit. See under AImatrites A140-L
Actual Sulfuric as Sulfuric Acid A90-L Ammon- Gelatine Dynamite and Ammon-
Acyl and Aryl Derivatives of Azidoditbio- Gelignite (British Not-Permitted (Ammo-
carbonic Acid A632-R nium Nitrate Dynamites) A368 (table)
,\erojet Propellants A1O%L Ammonium Acetate A27-R
A em jet Propellants. See under Ammonium Ammonium-AIuminum Alum Al56-L
Nitrate Blasting Explosives, High Ammonium Azide A521-L
Explosives and PropeIIants A350(table) Ammonium Azide Ammonates A521-R
Agglomeration or Caking and Its Prevention Ammoni urn Azidodithiocarbonate A634-L
c3-R Ammonium Chlorate C184-R
AggIutinant or Binder B120-R Ammonium Chrome Alum Al56-L
Airships ‘and Ballons; Application in War Ammoniurn-kon Alum A156-R
B 1O-L Ammonium Nitrate A311 to A340
Aitch-Tu-Ess. See under Asbestos A494-L Introduction A311
Akardit. See Acardite A7-R Historical A312
Aldehyde. See Acet aldehyde A 14-L Laboratory Preparation and Manufacture
Aldolcondensation Product of 5- A313 & A340
Aminotetrazole A260-R Explosive and Other Properties A318
Alizarine, Nitro Derivatives. See under Uses A334
Dihvdroxyanthraquinone Analytical Procedures, General A369
Alkali and Alkaline E arrh Salts of A zido- Analytical Procedures, Spencer Chemical
dithiocarbonic Acid A633-R co A379
Alkali Amides. See under Amides A 168-R US Specification Requirements and Tests
Allophanamide. Same as Biuret B 164-L A370
Allophonic Acidamide. Same as Biuret Ammonium Nitrate Blasting Explosives,
B 164-L High Explosives and Propellants A341
Allylazidodithiocarbonate A632-L to A354
Aluminum Acetylide A70-L Ammonium Nitrate Dynamite (AND) (American
Aluminum Azide A521-L and European Types) A355 to A356
Aluminum Carbide. See under Acetylides Ammonium Nitrate Explosions, Fires and
and Carbides A70-L Hazards A357 to A363
Aluminum Chlorate C 184L Ammonium Nitrate Explosives of Spencer
Aluminum Triazide A52 1-L Chemical Co A354 (table)
 C218

Ammonium Nitrate Explosives, Tests of Copper Acetylides A74

Spencer Chemical Co [a)cook-off tempera- Lead Azide A563-76
ture b)Detonation velocity c)Wax-gap Lead Azide Explosives A580-87
and d)Impact-friction pendulum] Potassium Chlorate C193-L
A354 (notes) Silver Acetylide or Silver Carbide A8 1-R
Ammonium Nitrate Fertilizer Grade (FGAN) Sodium Azicie A612-R to A619
A364 to A367
Sodium Chlorate C199-L
Ammonium Nitrate Gelatin (ANG) A367 to
Strontium Chlorate C201-L
A368
Anhydrobisinadandione. Same as Bindone
Ammonium Nitrate, US Military Specification
B121-R
Requirements and Tests A370
Aniline, Azido Derivatives A62FL
Amen-GeIatin Dynamite and Ammon-Gelignite
Aniline, AZO Derivatives A646L
(British Not-Permitted Ammonium Nitrate
Aniline, Azoxy Derivatives A665-L
Dynamites) A368(table)
Anisole, Azido Derivatives A629-R
Analytical Procedures for:
Ani sole, Azo-Derivatives A64GL
Acardites AFL
Anisole, Azoxy-Derivatives A665-R
Acetal A13-L Anthrachrysone, Tetranitro. Same as
Acet aldehyde A15-L
1,3,5 ,7-Tetrahydroxy anthraquinone,
Acetic Acid A25-R
Tetranitro
Acetic Anhy~ide A30-L
Anthragallol, Nitro Derivatives. See under
Acetins A32-L
Trihydroxyanthraquinones
Acetone A35-R
Anthrarufin, Tetranitro. Same as
Acetylides A63-R
1,5-Dihydroxyanthraquinone, Tetranitro
Aluminum A143-R
Antigrisou (Explosifs) A466-R
Amatol Al64-L
Antimony, Metal A467-R
Ammonal A292-R
Antimony, Analytical Procedures A469 to
Ammonia A303-L
A470
Ammonium Nitrate A369-L
Antimony Triazide A522-R
Ammonium Chlorate C 185-R
Arsenic Azide A522-R
Aniline and Derivatives A415
Arsenic Triazide A522-R
Anisole and Derivatives A454
Arsenium Carbide. See under Acetylides and
Antimony A469-70
Carbides A70-R
Barium Chlorate C 186-R
Aryl and Acyl Derivatives of Azidodithio-
Benzene, Nitro Derivatives B5 1-L carbonic Acid A632-R
BIack Powder B 176
Asc arite. See under Asbestos A494L
Camphor C2 1-R
Asphaltines. See under Asphalt A496-R
Cannon Propellants C38
Auric Imidoamide A 169-L
Carbazole C45
Aurous Azide or Gold Azide A536L
Carbon C57
Austrian Ammonals A289 & A290 (table)
Castor Oil C88-R
Azacyclobutadiene. See Azete A51&R
Cellulose and Its Esters(Except
9-Azafluorene. Same as Carbazole C45.L
Nitrocellulose) C99-L
Azeotropic Distillation Method for Moisture
Cellulose Nitrate Cl 19-R
Determination A370-R to A37 1-L
Centrality 1 C 129-R
Azide-Atyphnate-Aluminum. See ASA A493-R
Centrality 2 C 138-L
Centrality 3 C139-R Azidine or Acetazidine A24-R & A627-R
Azodicarbonhydrazide A271-L
Charcoal C150-L
1, I’-Azo-5 ,5’-di(p-tolyl)-tetrazole A266-R
Cheddites C161-L Azopicric Acid. See Hexanitroazophenol
Chlorates C 182-L
A658-L
 C 219

B l-benzyl-vic-tetrazole A191-L
Benzyl Azidodithiocatbonate A633-L
Backfire. See Backflash B2- R Benzylperacetate or Acetylbenzylperoxide
Ballistic Cap and Windshield A483-L A55-L
“Banana Oil. ” See Amyl Acetate A393-L Berdan Rifle. See Berdanka B 101-R
BARC. See under Amphibious Vehicles Beryllium Acetylide A70-R
A393-L Beryllium Azide. See Beryllium Diazide
Barium Acetylide A 70-R A524-R
Barium Azide. See Barium Diazide A523-L Beryllium Carbide. See under Acetylides and
Barium Chlorate C 185-R Carbides A7 1-L
Barium Nitroaminoguanidine A212-L Beryllium Diazide A524-R
Barium Picramate A242-L Betaphenylacrylophenone. Same as
Basic Cupric Azide A533-L Chalcone C 146-R
Belgium Ammonium Nitrate Gelatin Bibenzoyl. Same as Benzil B-64R
Dynamites A368(table) Bicarbonates and Carbonates C59-L
Benite. See under Black Powder Modifications Bikarbit or Bicarbite B1 11-R
B173-R Binding Energy. See under Atomic Energy
Benzalacetophenone. Same as Chalcone A500-R
C146-R Biphenylamines. See under Aminobiphenyls
Benzalaminoguanidini urn- 1,&dinitro- 2 A 191-L
Biphenyldiazonium Perchlorate. See under
-(aminoguanyl ~biguanidine Benzalhydramne
Aminobiphenyls A191-L
A215-L
p,p’ -Biphenylenebisazotrinitromethane A67-R
4-Benzeneazodiphenylamine or 4-Anilinoazo- Bi s-(aminoguanidinium} 1,6-dinitro-2-
benzene A420-R (aminoguanyl~biguanidine A214-R
Ben zeneazotrinitrom ethane and Derivatives Bis-(benzalaminoguani dinium} 1,6-di-
A67-R nitrobiguanidine A215-L
Benzenecarboxylic Acid. Same as Benzoic
Bi S(Carboxamide~acet ylene. See Acetylene-
Acid B69-R
dicarboxamide A65-L
1,3-Benzodiazole. Same as Benzimidazole
4,4’ -Bi s-dimethylamino-benzoph enone. See
B65-L Auramine A507-R
Benzodioxadiazine. Same as Benzofuroxan
Bi S( 1, l-dimethyl-2-propynyl yperoxide. See
B68-L A6GR
under Acetylene Hydroperoxides
Benzofurazan Oxide. Same as Benzofuroxan A525-L
Bi s(hydroxylamino) Azide
B68-L Bis(hydroxymethyl) methylaminomethane. See
Benzoglyoxaline. Same as Benzimidazole A232-R
Aminomethylpropanediol
B65-L
4-[Bi s(p-hydroxyphenyl)methylene]-2,5-
-.-13enzoh ydryl A zidodithiocarbonate A633-L cyclohexadien- l-one. See Aurine A508-R
l,2,3-Benzotriazino [3,4-4 perimidine. See Bi s(l-methyl- l-ethyl- 2-propynyl)-peroxide. See
under Aminophenylperimidines A246-L under Acetylene Hydroperoxides A66-R
2, 1,3-Benzoxadiazole. Same as Benzofurazan
Bis(3-methyl-2,4,6-trinitrophenyl)-amine. See
B67-R 2,4,6,2’,4’,6’ -Hexanitro-3,3’ -dimethyI-
Benzoylacetylperoxide or Acetylbenzoyl- diphenylamine A443-R
peroxide A54-R Bismuth Azide. See Bismuth Triazide A525-L
Benzoyl A xidodithiocarbonate A633-L Bismuth Azidodithiocarbonate A636-R
Ben zoylazidomethane or eAzidoaceto- Bismuth Triazide A525-L
phenone under Acetophenone A47-R 1,2- Bis(2-nitramino- 2-imidazolin- l-yl ~ethane
Benzozone or Acetylbenzoylpmoxide A54-R A220-R
Benzyl Abietate. See under Abietic Acid Bis-1-(2-nitroamino-2-imidazolinyl)-ethane
A3-R A220-R
Benzyl acetylperoxide or Acetylbenzyl- 1,2* Bis(2-nitrimino-3-nitro- l-imidazolidyl)-
peroxide A55-L ethane A220-R
1- Benzyl-5-amino-vic-tetrazole. See 5-Amino Bis- l-(3-nitro-2-imid azolidonyl)ethane
A221-L
 C 220

1,2-Bis(3-nitro-2-oxo- l-imidazolidyl) ethane Calibers of US Ammunition and Weapons

A386 to A.387
A221-L
Caliver. See under Arquebus A488-L
N’,Ns-Bis[a-tetrazolyl-5]-hexazidiene A260-R
Callou Powder. See under Chlorate
Bistriazomesidine. See 2-Amino-4,6-diazido-
Explosives c203-L
mesitylene A224-R
Canal (or Channel) Inclusion Compounds.
Bitumen. See under Asphalt A496-R
See under Clathrates and Other Inclusion
Blasting Gelatin A147 (table)
Compounds in Vol 3
Blend or Blended Nitrocellulose C106-L
Carbamylurea. Same as Biuret B164-L
Blue Steel Missile (Brit). See under Missiles
Carbenes. See under Asphalt A496-R
Boron Azide. See Boron Triazide A525-L
Carbides. See Acetylides and Carbides
Boron Carbide. See under Acetylides and
A69-R
Carbides A7 1-L
Carbonyl Di azide A528-L
Boron Triazide A525-L
Cellulose Triacetate. See under Acetyl
Breechflash. See Backflash B 2-R
Celluloids A55-R
British Ammonals. See under Ammonals
Cerium Azide. See Cerium Triazide A528-R
A289, A290 & A291-R
Cerium Hydroxydiazide A528-R
British Ammonium Nitrate Gelatin Dynamites
Cerium Triazide A528-R
A368(table)
Cesium Acetylide-Acety lene A72-L
Bromine Azide A525-R
A635-R Cesium Azide A528-R
Bromine Azidodithiocarbonate
p-Bromobenzoyl Azidodithiocarbonate A633-L Cesium Carbide A72-L
Brown Powder. See under Black Powder Cesium Hydrogen Acetylide A72-L
Chain Reaction. See under Atomic Energy
Modifications B 173-L
A501-L
1,4-Butanedicarboxylic Acid. See Adipic
Chishokianin. See 2,3 ,4, GTetranitroaniline
Acid A 104-L
A411-L
But anolaniline. See Anilinobutanol A422-R
Chlorine Azide or Chloroazide A529L
Butylcarbinol. See Amyl Alcohol A394-R
Chlorine A zidodithiocarbonate A635-R
Butyl Centrality. See Centrality, Butyl
Chloroazidine. See Azobi s-(chloroformami dine)
C140-L A652-R
1‘-Chloro-l-methyl-benzene. See Benzyl
c
Chloride B95-R
Chloronitroanilinopropanols A436.R
Cadmium Acetylide A71-L
@-Chlorotoluene. Same as Benzyl Chloride
Cadmium Amide Al69-L
B95-R
Cadmium Azide A526-L
Chocolate Powder. See under Black Powder
Cadmium Azidodithiocarbonate A63GR
Modifications B 173-L
Cadmium Diazide A526-L
Chromium Azide A530-L
Caesium and Caesium Compounds. See
Chromium Azide Complexes A530-R
under Cesium
Chromium Carbide. See under Acetylides and
Cage Inclusion Compounds. See Clathrates
Carbides A72-R
and Other Inclusion Compounds in Vol 3
Chromylacetylacetone. See under Acetyl-
Calcium Acetate A28-L
acetone A53-R
Calcium Acetylide A71-L
Clean Bomb (Hydrogen Bomb). See under
Calcium Azide A527-R
Atomic Bomb A499-R
Calcium Carbide. See under Acetylides and
CIuster, Aimable. See Aimable CIuster
Carbides A71-R
A114-L
Cal cium Carbide- Ammonia-Acet ylene A72-L
Cobalt Azide. See Cobalt Triazide A531-L
Calcium Carbide-Ammonia-Acetylene A72-L
Cobalt Azide Complexes A531-R
Calcium Diazide A527-R
Cobaltous Azetyl ide A72-R
Calcium Diazide Dihydrazinate A528-L
Cobalt Tri azide A531-L
Calcium Diazide Monohydrazinate A5 27-R
Calcium Hydrogen Acetylide Cold-Working, See Autofrettage A51O-R
A72-L
Calibers(hiillimeters vs Inches) Combustion and Burning. See Burning all,l
Combustion B343-L
A675 (Table II)
 C 221

Commercial Detonator. Same as Blasting Cap for Tanks A392-R

B185-L Depressive (or Regressive) Burning. See
Complex of Trinitroanisole A453-R Burning, Regressive B360-L
Compound CJ&N~OcP, caIled in Ger Demolition Hoses B16
‘%lpetersaure-diazophosp henylsaute Demolition Snakes B 16
A246-R Denigration of Cellulose Nitrate. See
Condensed Powders. See under Bulk and Cellulose Nitrate, Denigration of Cl 18-R
Condensed Powder B322-R Designolle & Casthelaz. See Casthelaz &
‘ CCook-Off” Temperature Test, as conducted Designolle C84-L
at the Spencer Chemical Co, Kansas Destruction of Amatol A 162-L
City, Mo A354 (Note a) Destruction of Black Powder B 177-R
Copper Acetylides, Analytical Procedures Destruction of Bombs B233-L
A74 to A76 Destruction (Disposal) of Lead Azide
Copper Azides. See A574-75
Cupric Azide A532-L Destruction Site or Burning Ground. See
Cuprous Azide A534-L Burning Ground etc B357
Copper Azidodithiocarbonate A636-R Detonating Cables B 16-R
Copper Nitroaminoguanidine A212-R Detonation, Advance. See Advance Deto-
Copper Picramate A242-L nation A105-R
Corrdlin. See Aurine A508-R Diacetin. See under Acetins A31-R
Coumarone. Same as Benzofuran B67-R Diacetone Diperoxide. See under Acetone
Critical Mass. See under Atomic Energy Peroxides A4 1-R
A501-L Diacetophenone Diperoxide. See Aceto-
Crossbow. See Arbalest A477-L phenoneperoxide, Dimeric A48-R
CSE Commission des Substances Explosives 1, 9Diacetoxy-2-acetyl-4,6,8-trinitro-2,4 ,6, &
(Explosif) (1902). See under Aluminum - tetrazanone or H-16. See under Acetyl-
Containing Explosives Al46-L diacetoxytetrazanonane A57-R
Cupric Acetylide A74-L 1,2-Diacetylethane. See Acetonylacetone
Cupric Amminoazide and Complexes A533-L A4GR
Cupric Azide A532-L Diacetylmethane. See Acetyiacetone A53-L
Cupric Azide, Basic A533-L Dialkyltetrazolylureas. See under Alkyl-
Cupric Azide Complexes A533-R tetrazolylureas A132-R
Cuprous Acetylide A72-L sym-Diaminourea. Same as Carbohydrazide
Cuprous Acetaldehyde Catalysts A74-L C54-L
Cuprous Acetylide A72-R Diaminoazoxybenzene. See Azoxyaniline
Cuprous Acetylide-CMoride A74-L .A@i5-L
Cuprous Azide A534-L 4,4’-Diaminobiphenyl. Same as Benzidine
Cuprous Hydrogen Acetylide A74-L B63-R
Cutocellulose. See under Adipocellullose Diaminohydroxytriazine Picrate. See Ammeline
A104-A1O5 P i crate A274-R
Cyanodiphenylamine. See Anilinobenzonitrile 4 ,6-Diamino-s-triazin- 2-ol. See Ammeline
A422-L A273-R
Cyanogen Azi dodithiocarbonate A635-R Diammonium-5-nitraminotetrazole A260-L
Cyanomethane. See Acetonitrile A45-L Diazobenzene Hydrate. Same as
Cyclohexatriene. Same as Benzene B41-R Benzenediazonium Hydroxide B55-L
Cyclotrimethyleneimine. See Azetidine Diazobenzene Nitrate. Same as
A519L Benzenediazonium Nitrate B56-L
Diazobenzene Oxalate. Same as
Benzendiazonium Oxalate B56-R
Diazobenzene Perchlorate. Same as
D Benzenediazonium Perchlorate B56-R
Diazobenzene Picrate. Same as
“cDavy Crock et” (Atomic Rifle) A504R Benzenediazonium Picrate B57-L
DD Device. See under Amphibious Devices Diazobenzene Sulfate. Same as
 C 222

Benzenediazonium Sulfate B57-L See under Acetylene Hydroperoxides

Diazobenzene Sulfocyanate. Same as A66-R
Benzenediazonium Sulfocyanate B57-L Dihydtoxyazobenzene. See Azophenol
Diazobenzene Sulfonic Acid and Derivatives. A657-L
See 13enzenediazonium Sulfonic Acid and Dihydroxyazoxyphenol. See Azoxyphenol
Derivatives B 57-L A671-L
Diazobenzene Tetrachloroiodide. Same as Dihydroxybiphenyl. Same as Biphenol
Benzenediazonium Tetrachloroiodide B122-L
B57-R Dihydroxybitolyl. Same as Bicresol B1 12-R
Diazobenzene Thiocyanate. Same as Dihydroxybutane or Butylene Glycol. Same
Benzenediazonium Sulfocyanate B57-L as Butanediol B368-R
Diazobenzene Tribromide. Same as Dihydroxydimethy lbiphenyl. Same as
Benzenediazonium Tribromide B58-L .Bicresol B 112-R
DiazoacetyIacetoneanhy dride. See 4-Acetyl 4,4’ -Dihydroxyfuchsone. See Aurine A50&R
-5-methyl- 1,2,3 -oxydiazoIe A84-L Dihydroxypropyl amine. See Aminopropanediol
Diazodinitrophenole. Same as Dinitrobenz- A25 1-L
enediazooxide B59-L 2 ,5-Diketohexane. See Acetonylacetone
( l-Diazo-3-nitrobenzene )-Perchlorate. Same A46-R
as m-Nitrobenzenediazonium Perchlorare Dimeric Acetone Peroxide A41-R
B56-R Dimeric Acetophenone Peroxide A48-R
Diazotetr azolephenylhydrazi ne. See N’ - Dime thoxyazobenzene. See Azoani sole
Amino-N’ -phenyl-N’-(tetrazolyl-5)- A646-L
triazine A247-R Dimethoxyazoxybenzene. See Azoxyanisole
Dibenzopyridine. See Acridine A94-L A665-R
Dibenzopyrrole. Same as Carbazole C45-L Dimethylaniline. See Aminoxylene A272
Dibenzoyl. Same as Benzil B64-R Dimethylarsenocy anide or Cacodyl Cyanide
Dicarbamylamine. Same as Biuret B164-L C 1-R
1, l-(N-Dichloramino)-5 -(p-tolyl).a-tetrazole Dimethyl azobenzene. See Azotoluene A660-L
A266-R Ilimethyl azoxybenzene. See Azoxytoluene
N,N’ -DichIoroazodic arboxamidine. See a, a’ - A672- L ,
Azobi s-(chIorof ormamidine) A652-R Dimethylazoethane. See Azopropane A65&R
Dicuproacetaldehyde A73-L Dimethylazoxyethane. See Azoxypropane
Diethoxyazobenzene. See Azophenetole A671-R
A65GR Dimethylbiphenyl. Same as Bitolyl B 163-L
Diethoxy azoxybenzene. See Azoxyphenetole 2,5-Dimethyl-2,5 -di-(t-butylperoxy Y3-hexyne.
A6 70-R See under Acetylene Hydroperoxides
1, l- Diethoxyethane. See Acetal A13-L A66-R
3-(P-Diethylamino ethyl)- a- sym-triazole 2,5-Dimethyl-2,5 -dihydroperoxy- 3-hexyne.
Dipicrate A209L See under Acetylene Hydroperoxides
Diethylene Glycol Monethyl Ether. Same as A66-R
“Carbitol” Solvent C51-R Dimethyldipheny lamine. See under Anilino-
1, l-Die thyl- 2-propynylhydroperoxide. See xylene A443-L
under Acetylene Hydroperoxides A66-L asym-Dimethylethyl ene Glycol. Same as iso-
7, 8-Dihydroacenaphthy lene. See Acenaphthene Butanediol i3370-L
A12-L Dimethylenemethane. See AIlene under
Dihydto-di keto- anthracene. See Anthraquinone Allenic Compoundq A133-R
A459-R Dimethylketone. See Acetone A33-R
Dihyrodiketobenzene. See Benzoquinone Di-(3-merhylpenty nyI~3-peroxide. See under
B79-R Acetylene Hydroperoxides A66-R
2,3-Dimethyl-l-pheny l-3-pyrazolin-5 -one.
5,6-Dihydro-6imino- s-triazine-2,4( lH,3H)-
dione. See Ammelide A273-L See Antipyrine A471-R
Dihydroxyazoben zene. See A zophenol 1,1-Dimethyl-2-propyny lhydroxide. See under
A657-L Acetylene Hydroperoxides A66-L
1,1’ -Dihydroperoxy-l, 1’ -dicyclohexylacety lene. Dinitrodiazobenzene Nitrate. Same as
 C 223

Dinitrobenzenediazonium Nitrate B56-R

E
Dioxybenzene. See Benzoquinone B79-R
Diphenic Acid or Biphenic Acid B121-R Effective Oxygen. See under Available Oxygen
Diphenol. Same as Biphenol B1 22-L A515-R
Diphenyl. Same as BiphenyI B 122-R Electric Blasting Squibs B212-R
Diphenylaminocarboxy lic Acid. See Electron Bomb B235
Anilinobenzoic Acid A421-R ‘ CEvanol”. See under AminoethylpolyvinyI
Diphenylamino-4-diazonium Hydroxide. See Alcohol A205-R
p-AniIinobenzenediazonium Hydroxide Energies, Activation.. See Activation Energies
A42 1-L A 1OO-Rto A 101-L
Diphenylbenzylamine. Same as Benzyl- Energy, Atomic. See Atomic Energy A500-L
diphenylamine B96-R Enheptin. See 2-Amino-5 -nitrothiazole A263-R
Diphenylcarbamy lallylamine. See N-Allyl Erosion of Propellants. See Burning, Erosive
-N’, N’-diphenylurea A 137-R B357-L
Diphenyldiimide. See Azobenzene A646-R Erosive Action of ACT 5 Propellant A98-L
Diphenyldiketone. Same as Benzil B64R Erosive Burning(in Propellants). See Burning,
DiphenyIeneimine. Same as Carbazole C45-L Erosive B357-L
s ym-Diphenylethane. Same as Bibenzyl B 11O-L Erosive Effect of Gas Flow. See Burning,
Diphenylglyoxal. Same as Benzil B64-R Erosive B357-L
Diphenylketone. Same as Benzophenone B77-L Erythrene. Same as Butadiene B365-R
Diphenylmethylamine. See under Aniiinotoluene Erythric Acid of Brugnatelli. See Alloxan
A438-L A134-R
N, N-Diphenylurea. See Acardie I A7-R Erythritetetrani trat e A147 (table)
1,3- or sym-Diphenylurea. Same as Carbanilide Ethanal. See Acetaldehyde A 14-L
C44-L Ethanaloxime. See Acetaldoxime AIGL
DiphenyIyI. Same as Biphenyl B 122-R Ethanamide. See Acecamide A16-R
sym-Dipicryl-urea B 156-L Ethaneamidine or Ethenylamidine. See a-
Dipotassium Hydrazobenziene-Azobenzene Amino-eimidoethane A223-L
A647-L Ethanoic Acid. See Acetic Acid A25-L
Dipotassium Salt of Nitroacetic Acid A27-R Ethanoic Anhydride. See Acetic Anhydride
Dipropyl Ketone or 4-Heptanone. Same as A29-R
Butyrone B393-L Ethanol amine. See Amino ethanol A200-L
Disol. See 2,4-Dinitroanisole A448-L @-Ethanolaniline. See under AminophenyI-
Disposal of Bombs I?234-L ethanol and under Anilinoethanol
Distyrylazobenzene. See Azostilbene A6 59-R A245-R & A424-L
Distyryl-benzene B 156-L Ethanoyl Bromide. See Acetyl Bromide
Disuccinyl Peroxide B 156-R A55-R
N‘ ,N6-(Ditetrazoly l-5)-hexazadiene A260-R Ethanoyl Chloride. See Acetyl Chloride
Ditetryl or BitetryI B 13 1-R A56-R
Dithiocarbonic or Dithioformic Acid, Azido Ethenylamidine or Ethaneamidine. See
Derivatives A632 a-Amino-a-imidoethane A223-L
Dirolylamine. See Anilinoxylene A443-L Ethine. See Acetylene A5%R
Dixylyl. Same as Bixylyl B 164-R Ethoxyacetanilide. See Acetamidophen&toIe
Double-Base Cannon Propellants C33-L A20-L
DUKW. See under Amphibious Vehicles A393-L Ethoxyaminobenzene. See Aminophenetole
Dumdum Bullets. See Bullets, Dumdum B331-R A240-R
Dummy and Blank Bullets. See Bullets, Blank EthoxyaniIine. See Aminophenetole A240-R
and Dummy B33 1-R Ethyl Abietate. See under Abietic Acid and
Dynamite O(French Ammonium Nitrate Non Derivatives A3-R & A4-L
-Permissible Gelatin) A368(table) Ethylacardite. See Acardite HI A8-R
Ethylacetic Acid or Butanoic Acid. Same as
Butyric Acid B391-L
Ethylaldehyde. See Acetaldehyde A14-L
Ethylamine. See Aminoethane A199-R
 C 224

3-@-Ethyl aminoethyl-&sym-tri azole)

F
Dipicrate A20&R
Ethyl aminotetrazoles. See under Amino-
Fallout. See under Atomic Energy A502-L
ethyl t etra zoles A20G17
False Ogive or Ballistic Cap A483-L
5- Ethyl amino- a-tetrazole A207-L
Felixdorf Factory Ammonals (Austrian)
Ethylaminotriazoles. See under Amino-
A289 (table)
ethyl triazoles A207-R
Ferric Azide A543-L
Ethylttzaurolic Acid. See under Azaurolic
Ferric Azide, Basic A543-R
Acids A517-R
Ferric Triazide. See Iron Azide A543-L
Ethyl Bromide. See Bromoethane B3 11-L
Ferrous Acetylide. See Iron Acetylide
Ethyl Centrality. Same. as Centrality 1
A76-R
Ethylene Aldehyde. See Acrolein A96-L
Ferrous Azide A543-L
EthyIenecarboxylic Acid. See Acrylic Acid
A96-R Filite~ See BALLISTITE, Italy, item e ‘~L
Ethylenedioxybenzene. Same as Benzodioxan Fission Bomb. See under Atomic Bomb A499-L
B 66-R Fission Reaction A501-L
N,N’ -Ethyleneguanidine. See under Amino- Flareback. See Backflash B2-R
imidazolines A219L Fluorine Azide A536-L
Ethyl enenaphthalene. See Acenaphthene Forcites(BeIgian & French Ammonium Nitrate
A12-L Non-Permissible Gelatins) A368(table)
Ethylidene Diethyl Ether. See Acetal A13-L Foriegn Cannon Propellants C37-L
Ethylidene Oxide. See Acetaldehyde A14-L Formula 266( Explosif). See under A1uminum
Ethylidene(2,4,6 trinitrophenylhy &azine). -Containing Explosives A146-L
See Acetaldehydepicrylhy&azone A15-L Frangible 3ullets. See i3ullets, Frangible I? 331-R
Ethylmethyl Centrality. Same as Centrality French Ammonals. See under Ammonals
3 C139-L A290 (table)
l- Ethyl- 2-nitramino-A2-imid azoline A220-R French Ammonium Nitrate Gelatin Dynamites
l- EthyI-2-nitrimino- 3-nitroimidazolidine A368 (table)
A221-L Fulminating Gold. See Auric Imidoamide
3-Ethyl- 1,2,4- txiazole-4-diazonium Hydroxide A169L
A208-R Fulminating Silver of Berthollet. See Silver
Ethyne. See Acetylene A58-R Amide under Amides A16>R
Eulite and its mercuric salt A67-R 3-Furazanacetic-4-carboxylic Acid A67-R
European Ammonium Nitrate Dynamites. See Furylacetamide. See Acetamidofuran A19-L
under Ammonium Nitrate Dynamites Fusion or Hydrogen Bomb. See under Atomic
A356 (tables) Bomb A499-L
Exploding Powder. See Bakufun B5-L Fusion Reaction. See under Atomic Energy
Ezplosif amylac~. See Amide (Explosif) A501-L
A16&L
Explosifs antigrisouteux A467- L
Explosion and Ignition of Anesthetic Agents
A402-L G
Explosion of Brominating Agents B305-L
E@osive Materials, Characteristic Data GaIcit. See under Asphalt-P erchlorate
fbafety) for C 148-R Castable Propellants A497-L
Explosives and Propellants, Characteristics ‘Gallium Triazide A536L
df C149-L Gas Bubbles in Explosives. See Bubbles of
Explosives Containing Aluminum A147 to A151 Gas, etc B320-L
Explosophores. See under Auxoexplose A5 13-R Gas Explosions, Action on Solid Propellants
Extinguishing Incediary Bombs B234-R A98-L
Exudation, Centrifuge Test for C 143-R Gas-Generati~g Cartridges. See under
Cartridges C70-R
Gasoline. Same as Benzin B66-L
Gasometric Method for Determination of
 C 225

Ammonium Nitrate Content by Nitrometer A21o-L

A373-77 Guided Missile Launcher. See under CANNON
Gas-Producing Cartridges. See under C29-L
Cartridges C70-R Gun. See under CANNON c26-R
Gelatin. See under American Dynamites,
Gelatinized Al67-L
Gel-CoaIites. See under American Dynamites,
Gelatinized AI67-L H
German AmmonaIs. See under Ammonals
A289 to A291 “H,” Symbol for N- Acetylamidomethyl-
Gessner Projectile. See under Arrow Pro- hexamethylenetetraminemononim~e
jectile A488-R A54-L
GiIsonite or MineraI Rubber. See under H-16. Symbol for 2-AcetyI- I, 9-diacetoxy-
Asphalt A496-R 4,6,8-trinitro-2,4,6,8-tetrazanonane
Glucinum or Beryllium B 107=L A57-R
Glycerol-~-monoamine. See 2-Amino 1,3- Halogen Derivatives of Anilinoethanol
propanediol A251-L A430 to A431
Glyceryl Diacetate. See Diacetin under Handling Bombs B238-L
Acetins A31-R Harquebus. See Arquebus A48&L
Glyceryl Monoacetate. See Monacetin under H Bomb (Hydrogen Bomb). See under Atomic
Acetins A31-R Bomb A499-L
Glyceryl Triacetate. See Triacetin under Heavy Metal- Salts of Azidodithiocarbonic
Acetins A31-R Acid A636-R
Glycine or Glycocoll. See Amino acetic Acid 4-Heptanone or Dipropyl Ketone. Same as
A178-L Butyrone B393-L
Glycol Monobutyl Ether or 2-ButoxyethanoI. Heptryl. See N-(2,4,6-Trinitro-N-nitranilino)
Same as Butyl “Cellosolve” 13381-R -trimethylolmethane Trinitrate under
Glycoluril. See Acetylenediurein A65-L Anilinotrimahylolmethane and Derivatives
Gold Acetylide A7GR A44 1-R to A442-R
Gold Amidoimide. See Auric Imidoamide Hepkylamines. See Aminoheptanes A215-R
A169-L Hexahydro-2 ,4,6-triimino-s-tri azine. See 1-
Gold Azide A53r$L Aminohexahydro- 2,4, 6-triimino- sym-triazine
Gold Azidodithiocarbonate A63 7-L A216-L
Gold Carbide A76-R 2,5-Hexanedione. See Acetonylacetone
Goose Missile. See Bull Goose or Goose A46-R
B340-R Hexanedionic Acid. See Adipic Acid AI04-L
Goudronite, Ammonite. See under Ammonite Hexanitrocarbanilide B 156-L
A31O-L 5-Hexen-2-one. See Allyiacetone A135-R
Grisonite or Mineral Rubber. See under Hexylamines. See Aminohexanes A215-R
Asphalt A4g6-R High Pan Fires (in manuf of Ammonium
Gri sou-dynamite roche (French Non- Nitrate) A31&L
Permissible Gelatin) A368 (table) High-Speed Photographic Cameras C 13-L
Grisounite couche and Grisounite roche Homologs of PentryI A429-R
A466-R (table) Howitzer. See under CANNON C27-L
Guanazine. See 4- Aminoguanamle A20FR Howitzer, RecoiIless Rifle& ChemicaI Shells.
Guanidine Azidodithiocarbonate A63GL See Chemical Gun, etc C174-L
Guanidinium-5-nitraminotetrazole A260-L Hybrid. See under Auxoexplose A5 14-R
Guanidinoethylaminoimidazoline, Nitrated Hydrazine Azide A536-R
Derivatives. See under Aminoimidazolin- Hydrazine Azide Hemiammonate A537-L
l-yl-ethylguanidine A222 Hydrazine Azide Monohydrazinate A537-L
Guanylaminotetrazole. See under 5-Amino- Hydrazobisformamidine. Same as Biguanidine
tetrazole A260-R B115-L
Guanylguanidine. Same as Siguanide B1 14-L Hydrazodicarbonamidine. Same as Biguanidine
Guanylhydrazine. See Aminoguanidine B115-L
 C 226

Hydrazoic Acid. See under Hydrogen Azide at the Spent er Chemical Co, Kansas
A539L City, Mo A354 (Note d)
Hydrogen Arsenide. See Arsine A491-L Initiation and Growth of Explosion B127L
Hydrogen Azide A537-R Inorganic Amides and Imides A 168-70
Hydrogen Azide, Anhydrous A53&L Inorganic Azides A520-A625
Hydrogen Azide, Aqueous or Hydrazoic Acid Inspection of Bombs B238-L
A539L Introduction to Vol 1 I-H
Hydroperoxides and Peroxides of Acetylene Iodine Azide or Iodoazide A542-R
Derivatives A66 Iron Acetylide A76-R
Hydroxyamines. See Aminoalcohols A17PL Iron Azide A543-L
2-Hydroxy-2- aminoimidazolidine. See 2- Iron Carbide. See under Acetylides and
Amino- 2-imidazolinol A222-L Carbides A76-R
Hydroxyaminomethy lpropane. See Amino- iso-Amylpicrate A39+R
methylpropanol A233-L Iso-Amylureidoacetyl Azide A399R
Hydroxy aminopropane. See Aminopropanol 2-Isocyanare Benzoylazide. See 2-Azido-
A253-L formylphenylisocy anate A63&R
Hydroxybenzotriazole. Same as Benzotrizolol Iso-Me-NENA. See Nitraminopropanol Nitrate
B87-R under Aminopropanols A253-L
@-Hydroxybutyraldehyde. See Acetaldol Iso5ctoic Acids, Aluminum Soaps A155-R
(Aldol) A15-R Isdpicramic Acid. See 2,6-Dinitro-4-amino-
Hydroxydiphenylamine. See Anilinophenol phenol under Aminophenol A243-R
A433-R Isoxazole, Amino-Diazo-and Nitro-Derivatives
~-Hydroxyethylamine. See Aminoethanol A67
A200-L &Isoxazoleazotrinitrom ethane A67-R
@-Hydroxyethylaminobenzene or /3-Hydroxy- Isoxazolecarboxy lic Acids A67
ethylaniline. See under Anilinoethanol 4-(4-Isoxalyl)-3-furazancarboxylic Acid,
A424-L Silver Salt A67-”R
l-(2-Hydroxyethyl)- 2-nitramino-A2-imidazoline Italian Ammonals A291R
A220-R Italian Military Aluminized Plactic Explosive
N-(@- Hydroxyethyl)-N’ -phenyl- 1, 2-diamino- Al48-L
ethane. See Anilinoethylaminoethanol Izod and Charpy Tests. See Charpy and
A431-L Izod Tests C154-L
l-Hydroxy- 2-propanone. See Acetol A33-R
Hydroxytoluene. Same as BenzyI Alcohol B91-L
2-Hydroxy-3,4, Grrinitroacetanilide. See under J
Acetamidophenol A21-R
Hypnone. See Acetophenone A47-L Japanese Explosives:
Ammonyaku A383-L
Angayaku A402-R
Chishokianin. See 2,3 ,4,6 -Tetranitroaniline
I A411-L
Type 91. See 2,4,6-Trinitroanisole A450-L
Type A or A(ko) Explosive A1lYL
Igniter Fuse or Bickford Igniter B 112-R JATO. See under ATO A497-R
Igniter Train or Burning Train. See Burning
Train etc B360-R
Ignition and Explosion of Anesthetic Agents
A402-L
K
Iminodihydropurine. See Aminopurine A254-L
Imirmdihychotriazine. See Aminotriazine
Kaliialmatrit. See under Almatrites A 140-L
A267-L
Kamikaze or Baka (Suicide) Bomb B4-R
2- Imino-1,3,4-thi adiazoline. See under
Karitto or Carlit C68-R
Aminothiadiazole A262-R
2-Ketotrimethyleneimine. See 2-Azetidinone
Impact-Friction Pendulum Test as conducted
A519-L
KI-Starch Test. See Abel’s Test A2-L Detn of Acidity in LA A571-R
Kreulen Aluminum Block A145-L Detn of Volubility of LA in HZO A572-L
Kynuric Acid. See under Carboxyphenyloxamic Detn of Sand Test Value for LA A572-L
Acid C66-L Dern of Moisture in LA A572-3
Detn of Ball Drop Test Value for LA
A573-L
Analysis of Ethyl Alcohol Solution A573-R
L Analysis of “Killing Tank” Liquid A573-R
Analysis of Nitric Acid Used for “Killing”
Lanthanum Triazide A544-R LA A574-L
Lead Acetates. See under Acetates A28 Disposal of Laboratory Samples Containing
to A29 LA (by Various Methods) A574-R to
Lead Aceto-Bromate A29-L A575
Lead Aceto-Chlorate A29-L Laboratory Test for the Presence of LA
Lead Aceto-P erchlorate A2+L A575-R
Lead Aceto-Sodiurn Perchlorate A29L Lead Azide, Various Military Types A557
Lead Acetylide A7GR to A563
Lead Azide (Lead Diazide) (LA) A545 to Dextrinated LA, Type I(US) A557& A559
A556 British(Service) LA A557 & A559
General Properties A545 to A550 Colloidal LA, Type II (US) A558 & A559
Laboratory Preparation A546 PVA (Polyvinylalcohol) LA A558& A559
Manufacture of Dextrinated Lead Azide Dextrinated Colloidal LA A558 & A559
A547 RD-1333 LA A558 & A559
Explosive Properties A548 RD-1343 LA A558 & A559
Destruction (Disposal or Killing) of Lead RD-1352 LA A559 & A560
Azide A550 Lead Azidodithiocarbonate A637-L
Uses of Lead Azide A551 Lead Imide A16$AL
Lead (IV) Azide A556L Lead Nitroaminoguanidine A212-R
Lead Azide Basic A555-R Lead Picramate A242-R
Lead Azide Explosive, Primer ~d Deto- LeRoux (Explosif) A14f+L
nator Compositions A576 COA580 Liardet Powder. See Acme Powder A93-R
Analytical Procedures: Limit Charge or Charge Limit Cl 5 1-R
Analysis of an Unknown Sample A580-R Liquid Air(Liquid Oxygen)-Aluminum
Analysis of mixtures: LA, Sb*SS, Explosives A154-L
PB(SCN)2 & KcIO, A580-R to A584-R List of Abbreviations, Code Names and
Analysis of Mixtures: LA, Sb2S3, KC1C4, Symbols Vol 1, Abbr 1-65; Vol 2, IX
glass & shellac A585-R List of Abbreviations for Books and Periodicals
Analysis of Mixtures: LA, Ba(NOJZ, Vol 1, Abbr 66-76 Vol 2, XI
basic LSt & Sb,~ A586-L Lithium Acetylides and Lithium Carbides
Analysis of Mixtures: LA & Al A587-R A77
Lead Azide, Plant Analytical Procedures Lithium Aluminohydride. See Aluminum-
A563 to A576 Lithium Hydride A154-R
Determination of Lead Nitrate A563 Lithium Azide A588
Detn and Tests for Dextrin A564 Low Density CeHular Explosives. See Cellular
Analysis of Lead Nitrate Dilution Tank Explosives of Low Density C94-R
A565
Analysis of Sodium Azide Liquor A565
Analysis of SA Feed Tank A567 M
Analysis of SA Dilution Tank A567
Detn of Lead Azide by the US Military Magnesi urn Acet~lide A 77-R
Specification Method A567 to A570 Magnesium Arsenide A491-L
Detn of LA by the US Navy Method A570-L Magnesium Carbide A77-R
Detn of LA by the British Method A570-R Magnesium Diazide A589-R
Detn of Total Lead Content in LA A571-R Magnesium-Methanol Explosives Al55-L
 C 228

Maintenance of Bombs B238-L A193-R

Malonylurea or Acid
Barbituric B 19-R Methylaminotetrazole. See Aminomethyl-
Manganese AceryIide A78-L
tetrazole A233-R to A234
Manganese Carbide A78-L Methylaminothiazole. See Aminomerhyl-
Manganese Diazide A589R thiazole A234-R to A235
Manometric Bomb. See Bomb Manometric
Methylaminotriazole. See Aminomethyltri-
B224R
azol e A235-L to A236
Mercuric Azide A590-L
A637-L Methylaniline. See under Aminotoluenes
Mercuric Azidodithiocarbon ate
Mercurous Azide A591-L A264-R ro A265
Mercury Acetylides A78 Methyl azaurolic Acid. See under Azaurolic
Mercur ous Azidodithiocarbonate A637-L Acids 4517-R
Mesidine. See Aminomesitylene A224R Methyl Azidodithiocarbonate A633-L
N,N’ -Mesoxalyl Urea. See Alloxan A134-R Methylbiphenylamine. See Aminomethyl-
‘ ‘Mets”, See under P araldehyde A14-R biphenyl A229-L
Metalammonium. See Ammonium Metal A31O-R Methylbromide. See Bromomethane B3 12-R
Metaldehyde. See under Acetaldehyde A 14R Methyl Centrality. Same as Centrality 2 C 137-L
Methanol-Aluminum (or Magnesium) Explo- Methyl Cyanide. See Acetonitrile A45-L
sives A155-L Methyldiphenylamine. See under Anilino-
Methazonic Acid. See Mononitroacetaldoxime toluene A438-L
A16-L N-Methyldipicry lamine. See 2,4,6,2’,4’,6’-
Methoxyacetanilide. See Acetamidoanisole Hexanitro-N-methyI-diphenylamine A440-R
A17-L Methylethylketone. Same as Butanone B374R
Methoxyaminobenzenes. See Aminoanisoles MethyIethylmethane. Same as n-Butane B366-R
A182-L Methyl Glycerol or Trihydroxybutane. Same as
Methoxybenzaldehyde. See Ani saldehyde Butanetriol B370-R
A444-R 3- Methyl- 3-hydtoperoxy- l-butyne. See under
Methoxybenzaldehyde-phenylhydrazone. See Acetylene Hydroperoxides A6&L
Anisaldehydepheny lhyhamne A445-L 3-Methyl- 3-hydtoperoxy- l-pentyne. See under
Merhoxybenzanilide. Same as Benzamidanisole Acetylene Hydroperoxide A6GL
B3 9-R a- Methylisoxazolecaboxy lic Acid. See under
Methoxybenzene. See Anisole A448 Acetylene-Nitric Acid Reaction Studies
Methoxybenzoic Acid. See Anisic Acid A67-L
A446-R l-Methyl- 2-nitramino-A2- imidazoline A220-R
Methoxybenzoylazi de. See Ani soylazide l-Methyl- 2-nitrimino- 3-nitroimidazolidine
A456-L A221-L
Methoxybenzyl Alcohol. See Ani syl Alcohol Methylnonylthiuronium Picrate A69-L
A456-R Methylphenyl amines. See under Amino-
Methoxyphenylaminotetrazoles. See under toluenes A265
Amino methoxyphenylterrazoles A22%L Methylphenylether. See Anisole A448
Methoxyphenyltetrazole. See Anisyltetraznle Methylphenylketone. See Acetophenone
A457-L A47-L
Methyl Abietate. See under Abieric Acid Methylphenylketoxime. See Acetophenone-
A4- L oxime A49-L
Methylacardite. See Acardite H A&L Methylphenyl Propane or Phenyl Butane. Same
Methylacetanilide. See Acetamidotoluene as Butylbenzene B380-R
A22-L Methyl Picrate. See 2,4,6-Trinitroanisole
Methyl acetyl Ether. See Acetone A33-R A450-L
Methylamine. See Aminomethane. A225-R 2-Methylpropane or Trimethylmethane. Same as
Methyl aminoguanidines. See under Amino- iso-Butane B368-L
methylguanidines A231-L Methyl-propanediol. Same as iso-Butanediol
Methyl aminonitroform. See Aminomethane B370-L
Nitroform A22 7-R Methyl-propanetriol or Trimethylolmethane. Same
Methyl aminophenols. See Aminocresols

.
1
 C 229

as iso-Butanetriol B371-R under Aminoethanol A201-L

Methylpyrrylketone. See AcetyIpyrrole A86-R Neutral Burning. See Burning, Neutral B3 58-L
hlethyltrimerhy lene Glycol. Same as iso NIBTN or Nitro-iso-butanetriol. See under
-Butanediol B370-L iso-Butanetriol B37 1-R
Military LNitrate of Ammonia. See Amatol Nickel Acetylide and Nickel Carbide A78-R
A158-L & A163-R Nickel Diazide A592-R
Mineral Pitch. See Asphalt A496-L Nickel Nitroaminoguanidine A2 13-R
Mineral Rubber or Gil sonite. See under Niter Cake. See Bisulfate, Sodium B 162-R
Asphalt A496-R Nitramide or Nitroxylamide Al 70-L
Miner’s Safety Fuse or Bickford Fuse B 112-L Nitramite. See Avigliana 3 A5 16-R
Misch Metal. See under Cerium Nitre-Bed or Caliche C&L
Modern Cameras C13-R Nitrocelluloses or Cellulose Nitrates C1OO-L
Moistute Determination in Ammonium Nitrate Nitrogen Oxides, Absorh=mt Matekials for
A370-R to A371-L A5-L
Mold and Bacteria Action on Nitric Esters and ~Nitro-a-i sonitrosoacetone. See Acet yl-
Smokeless Propellants B3-L methylnitrolic Acid A84-L
Mollit 3. Same as Centrality 3 C 139-L Nitrolit. See 2 ,4,6-Trinitroani sole A450-L
LMonacetin. See under Acetins A31-R Nitrolkrut or B erg (Explosive) B 10 1-R
Monoethanolarnine. See Aminoethanol Nitrometer Method for Determination of
A200-L Nitrogen Content in Nitrates A373 to
Monolene. See under Aminoethylation of N- A378
(2-Hydroxyprop yl )-ethyl enediamine 3-Nitropropene. See AHyl, Nitro A138-R
A203-L y-Nitropropylene. See Allyl, Nitro A139R
Mortar. See under CANNON C27-R Nitroso(N-so) (Nitrosylsulfuric Acid) Deter-
MSX. See l- Acetoxy-2 ,4,6- trinitro-2,4,6- mination’in Acids A8%R
triazaheptane under Acetoqtriazahept ane Nitrosyl Azide A594-L
A53-L Nitroxylamide or Nitramide A170-L
Mudcapping. See Adobe shooting under Nn030; Nn031; Nn032 and Nn033 (Explosifs)
Agriculture and Forestry Use of Explo- A148-L
sives A113-R Nomenclature Vol 1, II-VI
Musk Xylene. See TrinitroterbutylxyIene Non-P ermissible Ammonium Nitrate Gelatin
under Alkyd Resins A128-L Dynamites (American, Belgian and French)
Myrite. See under Carbon Disulfide C61-L A368 (table)
Not-P ermitted Ammonium Nitrate Gel atine
Dynamites (British) A368 (table)
Nuclear Bomb. See Atomic Bomb A49FL
Nuclear Energy. See Atomic Energy A500-L
N Nuclear Explosions. See Atomic Explosions
A501-R
p-Naphthalene. See Anthracene A457-R Nuclear Fission Weapons and Ammunition.
Naphthyleacetamide. See Acetamidonaphthalene See Atomic Weapons and Ammunition
A19-R A504
Naphthylacetate. See Acetoxynaphthalene Nuclear Reactions. See Atomic Reactions
A52-R A501-L
Naphthylamine. See Aminonaphthalene Nuevo Anagon (Spanish Ammonal) A289
A237-L (table)
~-Napthylazotrinitromethane A67-R
NATO Military Cartridges C76-L
Natriralmatrite. See under Almatrites A 140-L
NBSX. See ATX A507-L
Needle Point Projectiles. See Arrowhead
o
projectiles A489-L
Needle Shell. See Arrow Projectile A488-R Octahydro- l-acetyl- 3,5, 7-trinitro- s-tetrazo-
NENA. See l-Nitramino-2-ethaol Nitrate
tine. See l- Acetyl-3,5, 7-trinitro6cta-
 C 230

hydro- s-tetrazine, designated QDX or SEX under Acetophenone A47-R

A49-R Phenazone. See Antipyrine A471-R
Octyl. Same as Diteiryl or Bitetryl B 13 1-R Phenetidine. See Aminophenetole A240-R
Oil of Mirbane. Same as Mononitrobenzene Phenyl Abietate. See under Abietic Acid
B45-R A4-L
Ordnance Buildings and Other Structure. See N-Phenylacetaminde. See Acetanilide A22-R
Buildings, etc B320-R Phenyl Acetonitrile. See Benzyl Cyanide
Organic Amides and Imides “A170 & A171 B95-R
Organic Azides and Azido Derivatives P henylalanine. See under Anilinopropionic
A626 to A643 Acid A436-R
Oxalyl ethylester Azide. See Azidoijxalic Phenyldlylamine. See N-AIIylaniline A 136-R
acid Ethylester A641-L Phenylallylozonide. See Allylbenzeneomnide
Oxoethylpyrrole. See Acetylpyrrole A86-R ‘413 7-L
2-Oxrr4,4,6-trimethyltetrahydropyrimidine. Phenylaldehyde. Same as Benzaldehyde B35-L
See Anhydroacetoneurea A403-R Phenylamine. See Aniline A406
Oxygen Balance to CO(OB to CO) and Phenylaminobutanol. See Anilinobutanol
Oxygen Balance to CO,(OB to CO,). See A422-R
under Available Oxygqn A515 Phenylaminobutyric Acid. See Anilinobutyric
Oxyliquit A147(table) Acid A423-R
Phenylamino-4-& azonium Hydroxide. See
p-Anilinobenzenediazonium Hydroxide
P A421-L
Phenyl aminodihydroxypro pane. See Anilino-
Packing of Bombs B237-R propanediol A434-R
P spite. French for CWA Acrolein A90-L Phenylaminoethanol or Phenylethanolamine.
P araldehyde. See under Acetaldehyde A 14-R See under Anilinoethanols A424-L
P araldol. See under Acetaldol A 15-R Phenylaminogumidine. See Anilinoguanidine
Paris Gun & Other German Big Guns B 113-R A431-R
P entaerythritol-Ac etone Compounds. See 2-Phenylamino-2- methyl- 1,3-dihy&oxypropane.
Acetone Compounds of P entaerythritol See 2-Anilino-2-methyl- 1,3-propanediol
A40-L A433L
Pentaerythritolmonoally lether Trinitrate. See Phenylaminopropmol. See Anilinopropanol
2-AIIyloxymethyl-2-hydroxymethyI- 1,3- A436-L
propanediol Trinitrat e A138-R l-Phenyl-5- amin~tetraale. See under
2 ,4-Penranedione. See Acetylacetone A53-L Aminophenyltetrazol es A247-L
Pent anol. See Amyl Alcohol A394-R 5-Phenylamino-tetrazole. See Anilinotetrazole
P enthrinit A 147 (table) A437-L
Pentryl. See 2-(2’ ,4’ ,~Trinitro-N-nitranilino Phenylaminopropanediol. See AnilinoPro-
Ethanol Nitrate under Anilinoethanol and panediol A434-R
Derivatives A425-L to A429R Phenylaminopropanol. See Anilinopropaol
P entryl Homologs A42FR A436-L
Peracetic Acid, Benzylester. See Acetyl- Phenylamino-rrimethy lolmethae. See
benzyIperotide A55-L Anilinotrimethy lolmethane A44 1-L
Perbutyric Acid or Peroxybutyric Acid. Same as Phenylaniline. See Aminobiphenyl A 191-R
Butyrylhydroperoxide B394-L N-Phenylanthranilic Acid. See Anilinobenzoic
Peroxyacetic Acid, Butyl Esrer of. See Acid A421-R
Butyl Peroxyacetate B387-L Phenylazodiphenylamine A420-R
Peroxybenzoic Acid, Butyl Ester of. See Phenylazobenzoic Acid. See Azobenzene-
tert-Butyl Peroxybenzoate B387-R carboxylic Acid A6S0-R
Peroxybutyric Acid or Perbutyric Acid. Same as Phenylazoxybenzoic Acid. See Azoxybenzen~
Butyrylhydroperoxide B394-L carboxylic Acid A66&L
Peroxymonosulfuric Acid or Care’s Acid C69-L Phenylbenzene. Same as Biphenyl B122-R
Petroleum Benzin. Same as Benzin B66-L Phenylbenzylmine. Same as BenzyIaniline
Phenacyl Azide. See ti-Azidoacetophenone B93-L

. —... ———. . .. . . . ——.—

I
 C 231

Phenylbenzyl Ether. Same as Benzylphenyl 2 ,4,6-Trinitroanilino acetic Acid A420-L

Ether B99-L
2-(N-P icryI-N-nitramino} l-butanol Nitrate.
Phenyl Bromide. See Bromobenzene B308-R A423-L
See under Anilinobutanol
Phenyl Butane or Methylphenyl propane. Same 2-(N-P icryl-N-nitraminoY l-but~bl Nitrate.
as Butylbenzene B380-R
see 2-(N,2,4,6-Tetranitro anilino~ l-butanol
Phenylbutanone or Propyl Phenyl Ketone. Same A423-L
Nitrate
as Butyrophenone B393-R
a-p icrylnitramino- iso-butyric Acid. See
Phenylcarbamic Acid, Same as Carbanilic Acid A423-R
under Anilinobutyric Acid
C43-R
Picrylphenylenediamines. See Trinitroamino-
Phenyl Cyanide. Same as Benzonitrile B76-R
dlphenyl arnines under Aminodiphenyl-
o- Phenylene-formamidine. Same as Benzimida- A197
amines
zole B65-L
Picryltoluidine. See Trinitroanilinotol uenes
N, N-o-Phenyleneguanidine. See 2-Amino-
A4’3%R
benzimidazole A 187-L
Picrylurethane or Trinitrocarbanilic Acid
o-Phenylene-urea. Same as Benzimidazolone
Ethyl Ester C43-R
B65-R
PicrylurethyIan C44-L
Phenylethanolamine. See under Anilinoethanol
Plaster Shooting. See Adobe Shooting under
A424-L
Agriculture and Forestry Use of Explo-
PhenylfIuoroform. Same as Benzotrifluoride
sives A113-R
B89-L
Plastic Bomb. See Bomb, Plastic B225-L
Phenylformic Acid. Same as Benzoic Acid
Plosophore. See under Auxoexplose AS 14-L
B69-R
Polverifici Giovanni Stacchini SA (Esplosivo)
N-PhenylgIycine or Phenylglycocoll. See
A14%L
Anilinoacetic Acid A420-L
Polymer of Acetylacetone Peroxide A53-R
Phenylhydride. Same as Benzene B4 1-R
Polynirroalcohols, Ammonia Derivatives of
Phenylmercapran or Thiophenol. Same as
A306-L
Benzenethiol B63-L
Polynitroderivatives of Abietic Acid A3-R
Phenylmethanol. Same as Benzyl Alcohol
Potassium Acetylide A7FL
B91-L
Potassim-Alminum Alum A 156-R
N-Phenyl-N’,N’-phthaly lhydrazine. See
Potassium Amide or Potassamide A 169R
N-Anilinophthalimide A434L
Potassium Azide A594-R
PhenyIsulfochIoride. Same as Benzenesulfenyl
Potassium Azidodithiocarbonace A634-L
Chloride B61-L
PhenyItoIuidine. See under Anilinotoluene Potassium Carbide A79-L
A43&L Potassium Chrome Alum. See under Alums
PhenylcrimethyIolmethylamine. See Anilino- A15&R
Potassium Hydrogen Acetylide A79L
trimethylolmethane A44 1-L
Potassium-bon Alum A1>6-R
N-Phenyl-(tria-hy droxymethyl)-methylamine.
Potassium- 5-nitraminotetrazole A260-L
See’ Anilinotrimethy lolmethane A441-L
Potassium Picramate A242-R
Phenylxylidine. See Anilinoxylene A443-L
,Potatoes as a Source of Absorbent Materials
Phosphorus Carbide A7fkR
A5-R
Phosphorus-Nitrogen Azide A594-R
PhysicaI Tests Used to Determine Explo- Poudre ~ solvant or Poudre blanche. See B
sive and Other Properties Vol 1, VII (Poudre) 3 1-L
Picatinny Arsenal. See under Arsenals Poudres B Ballistic Homogeniety B5-R
A489-R Power Cartridges. See under Cartridges C70-R
Picramic Acid. See 2 ,&Dinitro- 2-aminophenol Power-Gas Generating Cartridges. See under
under Aminoph enols A24 1-R Cartridges C70-R
Picramide. See 2,4,6-Trinitroaniline A409-R Power-Generating Cartridges. See under
to A4 11-L Cartridges C70-R
Picric Powder. See Abel Powder Al-R Progressive Burning. See Burning Progressive
5-(P icrylamino)-a-cetrazole. See 5-(2’ ,4’,6’- B359-R
Trinitroanilino)-a-tetrazole A437-R Propadiene. See Allenic Compounds A 133-R
PropanoIamine. See Aminopropanol A253-L
N-PicryIgIycine or N-Picrylglycocoll. See
 C 232

Propanolaniline. See Anilinopropanol Analysis A99-L

A43GL RATO. See under ATO A497-R
Propanolon. See Acetol A33-R Recoilless Rifle, Howitzer & Chemical Shells.
2-Propanone. See Acerone A33-R See Chemical Gun, etc C174-L
Propellant Actuated Devices. See under Regressive (or Depressive) Burning. See
Cartridges C70-R Burning, Regressive B360-L
Propellant for Chemical Mortar, 4.2 inch. See Ricinus oil. See Castor oil C~7-L
Chemical Mortar, etc C176-R Ripping Ammonal A289(table)
Propenal. See Acrolein A96-L Rochling Anticoncrete Projectile. See under
Propeneamide. See Acrylamide A96-R Arrow Projectile A488-R
Propenenitrile. See Acrylonitrile A97-R Rocket Launcher or Rocket Projector. See
Propene- 1,2,3-tricarboxy lic Acid. See under CANNON C28-R
Aconitic Acid A93-R Rocket Propellants, Burning Characteristics.
Propylamine. See Aminopropane A25&L B350-R
Propenylanisole. See AnethoIe A402-R Rope, Chaff, and Window Countermeasures
Propylcyanide or Butanenitrile. Same as C145-R
Butyronitrile B393-L Rubidium AcetyIide A79L
Propyl Phenyl Ketone or Phenylbutanone. Same Rubjdium Azide A596-R
as Buryrophenone B393-R Rubidium Carbide A7YL
Pulsometer. See under Air Lifts A 118-L Rubidium Hydrogen Acetylide A7$AL
Pyriculine. See Azete A518-R Russian Ammonals A292-L
Pyridylamine. See Aminopyridine A254-R Russian Ammunition and Weapons A385-R
Pyrimidinetetrone. See AllOxan A 134-R Russian Mixture. See Ammontol A383-L
Pyroacetic Ether. See Acetone A33-R
Pyrocatechol. Same as Benzodioxan B66-R
Pyrocellulose, Pyro or Pyrocotton C 1os-L s
pyrocotton C105-L
Pyrotechnic Candle C24-R St Helen’s Powder. See under AmmonaIs
Pyrotechnic Compositions, Burning Character- A289 (table)
istics B355-R St John’s Bread or Carob-Bean C69-L
Pyrotechnic Compositions Containing: Salicylic Acid Triazoacetate. See under
Aluminum and Alloys A145, A153 & A154 Acetylsalicylic Acid A87-L
Antimony A468 Salite or Bergenstr6m (Explosive) B102-L
Auramin O A50%L “Salpetersaure-D iazophosphenyl saute” of
Pyroxylin or Collodion Cotton C 103-R Michaelis. See Compound CcH~N~OGP +
Pyruvic Alcohol. See Acetol A33-R 3H,0 A24GR
Pyruvonitrolic Acid. See Acetylmethyl- Screens. See Sieves A674 (Table I)
nitrolic Acid A84-L Self-Destroying Ammunition A391-R
Self-Hooping. See Autofrettage A51O-R
Semi-Gelatine (A British Ammonium Nitrate
Q Not-P ermitt ed Dynamite) A368 (table)
Setting Point Determination, See Solidification
QDX or SEX. See l-Acetyl-3,5,7-trinitro- Point Determination A612-L; C7-L
octahydro-s-tria.zinc A49-R Sevranite No 1 (Explosive) A148-L
Quaternary, Ternary and Binary Mixtures B 116-L SEX. See QDX A49-R
QuinolyIamine. See Aminoquinoline A255-R Shattering Effect or Brisance B26s-L
Quinone, See Benzoquinone B79-R Shipping & Transportation of Bombs B238-L
Quinonedioxime Peroxide. Same as Sieve s(Screens). Comparison of US, Tyler,
Benzofuroxan B68-L British and German Systems A674
(Table I)
Silicon Carbide A79-L
R Silicon Carbid~Aluminurn Oxide Fiber
A155-R
Radioactivation Analysis. See Activation Silicon Tetrazide A597-R

.— . . ...— —--.—.
.-—— “—=x
 C 233

Silver Acetylide, Analytical A81-R Space Travel. See Astronautics A49&L

Silver Acetylide, Destruction A81-R Spanish Ammonals A292-L
Silver Acetylide or Silver Carbide A79-R Special Bulldog Explosive. See Bulldog,
Silver Acetylide, Analytical and Destruction Special B 324-L
A81-R Specific Force and Berthelot’s Characteristic
Silver Acetylide Complexes A80-A81 Product B 105-L
Silver Amide A169R Spotter Tracer Bullet, See Bullets, Spotter
Silver Azide A597-R to A601-R -Tracer B332-L
Silver Azidodithiocarbonate A637-L Stabili& See Acardite I A7-R
Silver Nitroaminoguanidine A213-R Stilbeneazostilb ene. See Azo stilbene A659-R
Silver Picramate A242-R Storage Batteries. See Accumulators A 12-L
Single-Base Cannon Propellants. C3 1-R Storage of Bombs B237-R
Smoke Compositions Containing Auramine O Street Explosives. Same as Cheddites or
A 508-L Streetites C155-L
Smoke Pots. See Chemical Pots C177-L Streetites or Cheddites C155-L
Sodamide A170-L Strontium Acetylide or Strontium Carbide
Sodium Acetate A29-L A82-R
Sodium Acetylide A82-L Strontium Diazide A620-L
Sodium Aluminum Alum A157-L Styryl amine. See Aminost yrene A257-L
Sodium Amide A170-L Succinum. See Amber A 165-R
Sodium Azide (SA) A601 to A612 Suicide Bomb. See Baka Bomb 34-R
General Properties A601 to A603 & A605 Sulfurless Black Powder. See under Amide
to A607 (Explosif) A168-L ; B173-L
Laboratory Preparation and Manufacture Sulfuryl Diazide A62 1-R
A603 to A604 Surveillance of Bombs B238-L
Explosive Properties A604 to A605 Sylvic Acid. See Abietic Acid AZ-R
Uses A607 to A608
Sodium Azide, Plant Analytical Procedures
A612-R to A619
Analysis of Ammonia A612-R & A303 T
Analysis of .%dium Metal A612-R
Analysis of Wringer-Cake A6 13-L TATNB. Same as 1,3 ,5-Triazido-2,4 ,6-trinitro
Analysis of First Mother Liquor A613-R -benzene B43-R
Analysis of Second Mother Liquor A615-L TAX. See l-Aceto-3 ,5-dinitro-l ,3,5 -triaza-
Analysis of First Clear Liquor A615-L cyclohexane A50
Analysis of Lime Treatment Tank A615-R Ternary, Quaternary and Binary Mixtures B 116-L
Analysis of Second Clear Liquor A61GL a-Terpinene Peroxide. See Ascaridol A494-R
Anal ysis of Crude Sodium Azide Liquor Testing of Chemical Ammunition, See Chemical
A616-L Ammunition, Testing of C171-R
Analysis of SA, CrystSHine A617-L Tests (Physical) to Determine Explosive and
Calorimetric Determination of SA in Other Properties Vol 1, VII
Aqueous Ammonia A617-L Tetrahy&,ofuran or Tetramethylene Oxide. Same
Analysis of Technical SA Prepared from as Butylene Oxide B382-R
Hydrazine and Ethyl Nitrate A617-R Tetrahydroxyanthraquinone. See Anthra-
Sodi urn Azidodithiocarbon ate A634-R chrysone A458-R
Sodium Carbide A82-L 3,4,5, 6Tetrahydro-4,6- diimino- s-triazin-2
Sodium Hydrogen Acetylide A82-L (lH)-one. See Ammeline A273-R
Sodium Picramate A242-R Tetrahydroimida~ dlimidazole-2,5 (lH,3H)-
Sofranex A (Explosif) A148-L dione. See Acetylenediurein A65-L
Solidification Point Determination for Sodium Tetrahydro-3,3,5 ,5-tetrakis(hydroxymethyl)-
Azide A612R to A613L 4-oxypyrane. See Anhydroenneaheptitol
SP-42, SP-43, SP-45, SP-47 and SP-49 Pro- A404-L
pellants. See Aerojet Propellants A350 Tetrahydroxybiphenyl. Same as Biresorcinol
(table) B126-R
 C 234

2,2,4 ,4- Tetraki s(hydroxymethylnitrat e)- 1- Total Acidity as Nitric Acid A88-R
pyranol- l-nitrate. See Anhydroenneaheptitol Total Acidity as Sulfuric Acid A89-L
Pentanitrate A404-L Total Actual Acidity A90-L
Tetramethylammonium Azidodithiocarbonate Total Nitric as Nitric Acid A88 & A89
A637-R Total Sulfuric as Sulfuric Acid A89
Tetramethylazobenzene. See Azoxylene Transannular Photoperoxide of Anthracene
A662-L A438-R
Tetramethylazoxybenzene. See Azoxyxylene Transformation Products Formed During Aging
A673-L of Propellants C135-L, C139-L, C139-R,
Tetramethyl-biphenyl. Same as Bixylyl B 164-R C140-L, C 140-R
1, 1,4,4- Tetramethyl-2-butynyl enedihydro- Transportation & Shipping of Bombs B238-L
peroxide. See under Acetylene Hydro- Trench Mortar. See under CANNON C28-L
peroxides A66-R Tri acetin. See under Acetins A31-R
Tetramethyl-pz-diaminobenzophenone. See Triacetone Triperoxide. See under Acetone
Auramine A507-R Peroxides A42-R
Tetramethylene Oxide or Tetrahydrofuran. Trialkyls of Aluminum A144-R
Same as Butylene Oxide B382-R 3,4,5 -Triamino-a-sym-triazole. See 4-
Aminoguanazole A209-R
Tetramethyltetramethy lene-dihydro-peroxide.
2 ,4,6- Triaza-2,4 ,6-trinitro-hept an- 1-01
See 2,5-Bis (hydroperoxy-2,5-dimethyl)
-hexane B 144-R Acetate. See l-Acetoxy-2,4,6-trinitro-2,4,6-
triazaheptane or MSX A53-L,
Tetrane. Same as n-Butane B3.66-R
Tetranitro-carbanilide. See N,N’-B is(dinitro- 4-Triazoacenaphthene. See under Acenaph-
thenes A 12-R
phenyl)-urea under Bis(phenyl)-urea B 15 5-R
Triazoates. See Azides, Inorganic A520-L
Tetranitro-sym-dipheny l-urea. See N, N’-Bis
(dinitrophenyl)-urea under Bis(phenyl)-urea Triazo Compounds. See Azido Compounds
B155-R A626ff
Tetranitromethane, Manufacture from Acetylene lH-1,2,3-Triazole-4- ethylamine. See 4-(~-
Aminoethyl)-~vic-triazole A20%L
A67-L
Tetrazolo- 1, 2-azido-4-phthal azine- 1,2- 3-Triazopropene. See Allylazide A 137-L
Tribromomethane. See Bromoform B3 12-L
dihydtide. See (1’ -Azidophthalazine-4’ ,
‘rricrotonylidenetriperoxid e - tetramine.
5’ )-5,1-tetraZole A641-R
See under Amine Peroxides A17&L
Thallium Azide A621-R A637-R
Triethyllead Azidodithiocarbonate
ThaIIium Diethyl Picramate A243-L
Trihydroxybutane or Methyl Glycerol. Same as
Thallium Dimethyl Picramate A243-L
ButanetrioI B 370-11
Thallous A zidodithiocarbonate A637-L
4’,5,7- Trihydroxyff avone. See Apigenin
ThaIlous-Thallic Azide A623-R
A473-R
Thermonuclear or Fusion Bomb. See under
4,5,2’ -Trihydroxy-2-m ethyl anthraquinone. See
Atomic Bomb A499-L
Aloeemodine A140-R
Thiophenol or Phenylmercaptan. Same as
4’,5 ,7- Trihydroxy- 2-phenyIchromone. See
Benzenethiol B63-L
Apigenin A473-R
Thorium Dicarbide A82-R
Trimeric Acetone Peroxide. See under
Tin Azide A624-L
Acetone Peroxides A42-R
Titanium Carbide A82-R
Trimeric Methyleneaniline. See Anhydro-
Titanous Chloride Method for Determination
formaIdehydeaniIine A404-R
of Nitrobenzene in Aniline A4 15-R
Trim ethyl aniline. See Aminohemimellitene
TNTAB. Abbr for 2,4 ,6-Trinitro-l,3 ,5-triazido
A215-R
-benzene B43-R
Trimethylaniline. See Aminomesitylene
TNT Recovery from Scrap Amatol A 161-L A224-R
Toluidine. See under Aminotoluenes A265-R Trimethyanilines.
Tolylamine. See under Aminotoluenes See Aminohemimellitene A215-R
A264-R
See Aminomesitylenes A224-R
Tolyltetrazolonimide. See under Amino-
See Aminopseudocumens A254-L
tolylt etrazoIes A265-R Trimethyl-[3-azido-5 -nitro-4-hydroxy-pheny l]-

————.—.. . ---—. .—-. . . ..-___ .--—._—_ .———

 C 235

ammonium Hydroxide. See 2- Azido-6-nitro- Vinylethylene. Same as Butadiene B365-R

1,4-benzoquinone-4-trim ethyl imide ‘
A640-R
Trimethyleneimine. See Azetidine A5 18-R w
Trimethylmethane or 2-Methylpropane. Same
as iso-Butane B 368-L Water(or Methanol~Aluminum(or Magnesium)
Trimethylolmethane or Methyl-propanetriol. Explosives A 155-L
Same as iso-ButanetrioI B37 1-R Wax-Gap Test as conducted at the Spencer
N-( Trimethylolmethane)-ailine. See Chemical Co, Kansas City, Mo A354,
Anilinotrimethy lolmethane A441-L Note c
2,4 ,6- Trimethyl- 1,3 ,5-trioxane, See White German Powder. See Augendre Powder
P araldehyde under Acetaldehyde A14-R A507-L
Trinirrides. See Azides, Inorganic A520 Window, Chaff, and Rope Countermeasures
to A625 C145-R
Triphenylmethyl Azidodithiocarbonate A633-R Window Projectile or Chaff Shell C146-L
1,3 ,5- TriphenyI-trimethyl enetriamine. See Windshield and Ballistic Cap A483-L
Anhydroform aldehydeaniline A404-R Wolfram Carbide. See Tungsten Carbide
Triple-Base Cannon Propellants C37-L A82-R
Tungsten (or Wolfram) Carbide A82-R
Type 2 Explosives B2-R
Type 91 Explosive (Japanese) A450-L x
Type A Explosive (Japanese). See A(ko)
Explosive A1l YL Xylidene. Same as Aminoxylene A272
Xylonite or Celluloid C95-L
Xylylamine. See Aminoxylene A272-L
u

Unstable Burning (in Rocket Motors). See Y

Burning, Unstable B361-L
p-Urazine. See 4-Aminourazole A272-L Y-gun. See under Cartridge, Depth Charge
Urethane-morpholine. Same as N (or 4) Projector C80-L
-Carboethoxy-morpholine C53-L
US Ammunition and Weapons (Calibers) z
A386-87
US Military Cartridges C73-R Zeltit or Celtite C125-R
Zinc Acetylide A83-L
Zinc Azide A624-L
v Zinc Azidodithiocarbonate A637-L
Zinc Diazide A624-L
Vanadium Carbide A83-L Zirconium Carbid& A83-L
Vinylaniline. See Aminostyrene A257-L Zylonite or Celluloid C95-L
Vinyl Carbinol. See Allyl Alcohol A 135-R

* U.S. GOVERNMENT PR~JNG OFFICE: 1976 0- 595-870

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