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132 AROMATIC NITRO COMPOUNDS explosives that are quite as necessary as TNT for military purposes Effects of Substituents on Explosive Strength Bomb experiments show that tnnitrobenzene is the most powerful explosive among the nitrated aromatic hydrocarbons. One methyl group, as in TNT, reduces its strength, two, as in TNX, reduce it further; and three, as in tnnitromesitylene, still further yet. The ammo and the hydroxyl groups have less effect than the methyl group, indeed, two hydroxyl groups have less effect than one methyl—and tnnitroresorcmol is a stronger explosive than TNT, though weaker than TNB TNT is stronger than trmitrocresol, which differs from it m having an hydroxyl group The figures given below were determined by exploding the materials, loaded at the density indicated, in a small bomb, and measuring the pressure by means of a piston and obturator Density of loading is grams of explosive per cubic centimeter of bomb capacity. Trimtrobenzene Trinitrotoluene Tnnitro-TO-xylene Tnnitromesitylene . Tnnitrophenol (picric acid) Tnnitroresorcinol (styphinic acid) Trinitroamline (picramide) Tnnitro-TO-cresol Tnnitronaphthalene Pressure: Kilograms per square centimeter Density of loading: 0 20 2205 1840 1635 1470 2150 2080 2080 1760 0 25 3050 2625 2340 2200 3055 2840 2885 2480 2045 0 30 4105 3675 2980 2780 3865 3940 3360 2670 Similar inferences may be made from the results of lead block tests. Fifteen grams of the explosives produced the expansions indicated below, each figure representing the average from twenty or more experiments:
MONO- AND DI-NITROBENZENE 133 Trinitrobenzene 480 cc. Trinitrotoluene 452 cc. Picric acid 470 cc. Trinitrocresol 384 cc. Trinitronaphthalene 166 cc. Mono- and Di-Nitrobenzene Nitrobenzene is a pale yellow liquid, b.p. 208.0°, which is poisonous and has an almondlike odor closely resembling that of benzaldehyde (which is not poisonous). It is used as a component of certain Sprengel explosives and as a raw material for the preparation of aniline and of intermediates for the manufacture of dyestuffs and medicinals. Its preparation, familiar to every student of organic chemistry, is described here in order that the conditions for the substitution of one nitro group in benzene may serve us more conveniently as a standard for judging the relative ease and difficulty of the nitration of other substances. Preparation of Nitrobenzene. One hundred and fifty grams of concentrated sulfuric acid (d. 1.84) and 100 grams of nitric acid (d. 1.42) are mixed in a 500-cc. flask and cooled to room temperature, and 51 grams of benzene is added in small portions at a time with frequent shaking. Shaking at this point is especially necessary lest the reaction suddenly become violent. If the temperature of the mixture rises above 50-60°, the addition of the benzene is interrupted and the mixture is cooled at the tap. After all the benzene has been added, an air condenser is attached to the flask and the material is heated in the water bath for an hour at 60° (thermometer in the water). After cooling, the nitrobenzene (upper layer) is separated from the spent acid, washed once with water (the nitrobenzene is now the lower layer), then several times with dilute sodium carbonate solution until it is free from acid, then once more with water, dried with calcium chloride, and distilled (not quite to dryness). The portion boiling at 206-208° is taken as nitrobenzene. m-Dinitrobenzene, in accordance with the rule of Crum Brown and Gibson, is the only product which results ordinarily from the nitration of nitrobenzene. Small amounts of the ortho and para compounds have been procured, along with the meta, from the nitration of benzene in the presence of mercuric nitrate. 2 Dinitrobenzene has been used in high explosives for shells in mixtures with more powerful explosives or with ammonium nitrate. Its use 2 Davis, /. Am. Chem. Soc, 43, 598 (1921).
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CHAPTER I PROPERTIES OF EXPLOSIVES
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HIGH EXPLOSIVES 3 they are heated o
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HIGH EXPLOSIVES 5 black match may b
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A COMPLETE ROUND OF AMMUNITION 7 f
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A COMPLETE ROUND OF AMMUNITION 9 11
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DETONATING FUSE 11 ting upon, say,
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DETONATING FUSE 13 branch line squa
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FIGURE 8. Pierre-Eugene Marcellin B
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VELOCITY OF DETONATION 17 placed up
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FIGURE 10 Charles Edward Munroe (18
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Sensitivity Tests SENSITIVITY TESTS
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TESTS OF EXPLOSIVE POWER AND BRISAN
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BOERHAAVE ON BLACK POWDER 29 Bertho
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BOERHAAVE ON BLACK POWDER 31 powder
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GREEK FIRE 33 And of the last two o
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ROGER BACON 35 only half filled wit
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ROGER BACON 37 large as the human t
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DEVELOPMENT OF BLACK POWDER 39 Deve
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DEVELOPMENT OF BLACK POWDER 41 the
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USES OF BLACK POWDER 43 Potassium n
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MANUFACTURE 45 rings and in other p
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ANALYSIS 47 caded, and is never app
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AMMONPULVER 49 ing is made from sod
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OTHER PROPELLENT EXPLOSIVES 51 toge
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PYROTECHNIC MIXTURES 53 colors. His
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PYROTECHNIC MIXTURES 55 composition
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PYROTECHNIC MIXTURES 57 and moisten
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PYROTECHNIC MIXTURES 59 chloride is
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PYROTECHNIC MIXTURES 61 positions w
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COLORED LIGHTS 63 flares during the
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Potassium chlorate Strontium nitrat
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Barium nitrate Potassium nitrate Po
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LANCES 69 minute with an illuminati
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PICRATE COMPOSITIONS 71 To be burne
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ROCKETS 73 is used in whistling fir
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ROCKETS 75 one ounce and a half. It
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ROCKETS 77 which handle a gross of
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Roman Candles ROMAN CANDLES 79 Roma
Page 81 and 82: STARS 81 the space between the star
Page 83 and 84: STARS 83 4-ply manila paper tubing,
Page 85 and 86: STARS 85 YVeingart 31 reports compo
Page 87 and 88: STARS 87 powder mixture, given a ye
Page 89 and 90: GERBS 89 Gerbs Gerbs produce jets o
Page 91 and 92: WHEELS 91 denly with a terrifying r
Page 93 and 94: PINWHEELS 93 Pinwheels To make pinw
Page 95 and 96: PINWHLELS 95 need of a vast theater
Page 97 and 98: MINES 97 match or fire wick), for t
Page 99 and 100: COMETS AND METEORS 99 an electric o
Page 101 and 102: BOMBSHELLS 101 the short pieces sep
Page 103 and 104: BOMBSHELLS 103 is folded, rubbed, a
Page 105 and 106: TOY CAPS 105 "It is to be noted," h
Page 107 and 108: JAPANESE TORPEDOES 107 minate but w
Page 109 and 110: RAILWAY TORPEDOES 109 hardens it),
Page 111 and 112: CHINESE FIRECRACKERS 111 English Cr
Page 113 and 114: CHINESE FIRECRACKERS 113 carrying o
Page 115 and 116: CHINESE FIRECRACKERS 115 struck a s
Page 117 and 118: SPARKLERS 117 is shaped by a motion
Page 119 and 120: PHARAOH'S SERPENTS 119 Wire Dips an
Page 121 and 122: BLACK NON-MERCURY SNAKES 121 pellet
Page 123 and 124: Potassium chlorate Lactose Paranitr
Page 125 and 126: CHAPTER IV AROMATIC NITRO COMPOUNDS
Page 127 and 128: EFFECT OF GROUPS ON FURTHER SUBSTIT
Page 129 and 130: UTILIZATION OF COAL TAR 129 the nuc
Page 131: UTILIZATION OF COAL TAR 131 In each
Page 135 and 136: TRINITROBENZENE 135 powder, 250 lit
Page 137 and 138: TRINITROBENZENE 137 + CHsONo H. ,OC
Page 139 and 140: TRINITROBENZENE 139 According to Da
Page 141 and 142: TRINITROTOLUENE 141 not yet been de
Page 143 and 144: TRINITROTOLUENE 143 ?mall amount, p
Page 145 and 146: TRINITROTOLUENE 145 with a correspo
Page 147 and 148: TRINITROTOLUENE 14? The soluble sul
Page 149 and 150: TRINITROTOLUENE 149 cent free SOa)
Page 151 and 152: TRINITROTOLUENE 151 CH, NO, " ~" a
Page 153 and 154: TRIXITROXYLENE 153 Dautriche found
Page 155 and 156: NITRO DERIVATIVES OF NAPHTHALENE I5
Page 157 and 158: NITRO DERIVATIVES OF NAPHTHALENE 15
Page 159 and 160: PICRIC ACID 159 of biphenyl. The mo
Page 161 and 162: PICRIC ACID 161 dinitrophenol as re
Page 163 and 164: PICRIC ACID 163 a yellow nitropheno
Page 165 and 166: PICRIC ACID 165 below have been pub
Page 167 and 168: AMMONIUM PICRATE 167 80° and 90°
Page 169 and 170: TR1NITR0ANIS0L AND TRINITROPHENETOL
Page 171 and 172: TRINITROANISOL AND TRINITROPHENETOL
Page 173 and 174: TETRANITROANILINE 173 Both trinitro
Page 175 and 176: TETRYL 175 TNA shows about the same
Page 177 and 178: TETRYL 177 All the above-indicated
Page 179 and 180: TETRYL 179 m-nitrotetryl is effecti
Page 181 and 182: TETRYL 181 The solubility of tetryl
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BUTYL TETRYL 183 MINIMUM CHARGE FOB
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HEXANITRODIPHENYLAMINE 185 Carter 1
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HEXANITRODIPHENYL SULFONE 187 pound
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HEXANITROAZOBENZENE 189 nitrocarban
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CHAPTER V NITRIC ESTERS Nitric este
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METHYL NITRATE 193 sion of 24.5 mm.
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NITROGLYCERIN 195 blasting cap will
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NITROGLYCERIN 197 are evolved, but
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NITROGLYCERIN 199 than half its own
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NITROGLYCERIN 201 Thus, if 100 gram
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NITROGLYCERIN 203 quickly into a dr
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NITROGLYCERIN 205 "boils" strongly.
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NITROGLYCERIN 207 because the boili
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NITROGLYCERIN 209 the temperature r
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NITROGIA'CERIN 211 velocities of de
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NITROGLYCERIN 213 material in safet
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DINITROGLYCERIN 215 cerin. It mixes
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DINITROGLYCERIN 217 Both of the din
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NITROGLYCIDE 219 oxide ring, and mo
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DINITROCHLOROHYDRIN 221 can be froz
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NITROGLYCOL 223 amount is necessary
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NITROGLYCOL 225 portions with water
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TRINITROPHENOXYETHYL NITRATE 227 me
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PENTRYL 229 Another portion of the
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PENTRYL 231 tetryl by one of 27.5 c
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TRIMETHYLENE GLYCOL DINITRATE 233 i
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Butylene Glycol Dinitrate NITROERYT
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NITROMANNITE 23? While its stabilit
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NITRATED SUGAR MIXTURES 239 fact th
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NITROLACTOSE 241 Nitroglucose (d-Gl
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OTHER NITROSUGARS 243 readily solub
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EARLY HISTORY OF NITRATED CARBOHYDR
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NITROCELLULOSE 257 The two substanc
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NITROCELLULOSE 259 dre B. Either CP
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NITROCELLULOSE 261 nent materials w
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NltfROCELLULOSE 263 The pulped fibe
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NITROCELLULOSE 265 cellulose with g
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DURATION AT 1st period 2nd period 3
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DETERMINATION OF NITROGEN 269 upon
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DETERMINATION OF NITROGEN 271 actio
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NITROSTARCH 273 At the beginning of
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NJTROSTARCH 275 the contents of the
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UTILIZATION OF FORMALDEHYDE 277 cat
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PENTAERYTHRITE TETRANITRATE 279 ery
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DIPENTAERYTHRITE HEXANITRATE 281 ni
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TRIMETHYLOLNITROMETHANE TRINITRATE
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NITROPENTANONE AND RELATED SUBSTANC
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CHAPTER VI SMOKELESS POWDER An acco
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BULK POWDER 289 was called E C. pow
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BULK POWDER 291 FIGURE 71. Sweetie
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EARLY HISTORY OF COLLOIDED POWDERS
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EARLY HISTORY OF COLLOIDED POWDERS
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COLLOIDED NITROCELLULOSE POWDERS 29
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MANUFACTURE OF SINGLE-BASE POWDER 2
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STABILIZERS 307 Stabilizers The spo
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STABILIZERS 309 stable as those con
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TRANSFORMATIONS DURING AGING OF POW
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ABSORPTION OF MOISTURE 313 ence is
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ABSORPTION OF MOISTURE 315 ences. E
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CONTROL OF RATE OF BURNING 317 GAIN
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CONTROL OF RATE OF BURNING 319 Prog
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GELATINIZING AGENTS 321 but very li
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FLASHLESS CHARGES AND FLASHLESS POW
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BALL-GRAIN POWDER 329 in the presen
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CHAPTER VII DYNAMITE AND OTHER HIGH
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INVENTION OF DYNAMITE 333 The next
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INVENTION OF AMMONIUM NITRATE EXPLO
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GUHR DYNAMITE 337 which is practica
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STRAIGHT DYNAMITE 339 but "40% ammo
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STRAIGHT DYNAMITE 341 Munroe and Ha
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BLASTING GELATIN 343 of nitroglycer
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GELATIN DYNAMITE 345 night, and the
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PERMISSIBLE EXPLOSIVES 347 that one
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PERMISSIBLE EXPLOSIVES 349 many cla
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PERMISSIBLE EXPLOSIVES 351 The Fren
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Nitroglycenn Potassium nitrate Sodi
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LIQUID OXYGEN EXPLOSIVES 355 The Pr
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CHLORATE AND PERCHLORATE EXPLOSIVES
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AMMONIUM NITRATE MILITARY EXPLOSIVE
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CHAPTER VIII NITROAMINES AND RELATE
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METHYLNITRAMINE 371 Methylnitramine
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NITROUREA 373 filled with a strong
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GUANIDINE NITRATE 375 Guanidine or
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GUANIDINE NITRATE 377 The cyanamide
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GUANIDINE NITRATE 379 only one mole
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NITROGUANIDINE 381 been found, as d
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NITROGUANIDINE 333 mixture, is trea
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NITROGUANIDINE 385 A solution of ni
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NITROGUANIDINE 387 Nitroguanidine,
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NITROGUANIDINE 389 material "firmly
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NITROSOGUANIDINE 391 stant volume o
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ETHYLENEDINITRAMINE 393 rial which
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DINITRODIMETHYLSULFAMIDE 395 gives
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CVCLOTRIMETHVLENETRINITRAMINE 397 r
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CYCLOTRIMETHYLENETRINITRAMINE 399 r
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DISCOVERY OF FULMINATING COMPOUNDS
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DISCOVERY OF FULMINATING COMPOUNDS
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MERCURY FULMINATE 405 cold anvil an
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MERCURY FULMINATE 407 water, filter
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MERCURY FULMINATE 409 HgSA + NaCN +
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MERCURY FULMINATE 411 mented with s
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DETONATORS 413 Amusements with Fulm
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DETONATORS 415 characters of the ch
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DETONATORS 417 potassium chlorate.
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DETONATORS 419 in the amount of san
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TESTING OF DETONATORS 421 pressed.
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TESTING OF DETONATORS 423 later rec
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LEAD AZIDE 425 used; the azide is e
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LEAD AZIDE 427 the interaction of h
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LEAD AZIDE 429 of which there exten
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SILVER AZIDE 431 temperature of spo
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CYANURIC TRIAZIDE 433 The best resu
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EXPLOSIVE Cyanuric triazide Lead az
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TRINITROTRIAZIDOBENZENE 437 purifie
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NITROGEN SULFIDE 439 acid, sulfur d
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DIAZONIUM SALTS 441 A 0.05-gram sam
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DIAZODINITROPHENOL 443 Preparation
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DIAZODINITROPHENOL 445 alcohol 2.43
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TETRACENE 447 its structure. It is
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TETRACENE 449 Preparation 0} Tetrac
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HEXAMETHYLENETRIPEROXIDEDIAMINE 451
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FRICTION PRIMERS 453 which had been
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PERCUSSION PRIMERS 455 or with wate
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PERCUSSION PRIMERS 457 is safest to
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Aaronson, 158, 226 Abel, 42, 194, 2
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Ge, 241 Geschwind, 151 Gibson, 127,
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Pliny, 35 Prentice and Co., 253 Pre
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INDEX OF SUBJECTS Alkylnitroguanidi
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Ballistite, attenuated, 259 erosive
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Carbon tetrabromide, 375 Carbon tet
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Dehydrating press, 299, 300, 302 De
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Ether, solvent, 135, 152, 169, 181,
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Gold, fulminating, 3, 400, 401 Gold
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K KI starch test, 268, 285 Kekule o
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Methylglucoside tetranitrate, 243 M
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Nitromaltose, 240, 241 Nitromannite
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Picric acid, Trauzl test, 211, 231
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Salt, common (sodium chloride), 60,
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Strength of dynamite, 338, 339, 341
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Trinitrobenzene, sensitivity to imp
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