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284 NITRIC ESTERS At a time when the only practicable methods for the preparation of nitromethane were the interaction of methyl iodide with silver nitrite and the Kolbe reaction from chloracetic acid, the explosive was far too expensive to merit consideration. The present cheap and large scale production of nitromethane by the vapor-phase nitration of methane and of ethane has altered the situation profoundly. Trimethylolnitromethane trinitrate is an explosive which can now be produced from coke, air, and natural gas. Nitromethane too has other interest for the manufacturer of explosives. It may be used as a component of liquid explosives, and it yields on reduction methylamine which is needed for the preparation of tetryl. The crude trimethylolnitromethane from the condensation commonly contains a small amount of mono- and dimethylolnitromethane from reactions involving one and two molecules of formaldehyde respectively. It is recrystallized from water to a melting point of 150°, and is then nitrated. Stettbacher reports that the pure substance after many recrystallizations melts at 164-165°. The nitration is carried out either with the same mixed acid as is used for the nitration of glycerin (40% nitric acid, 60% sulfuric acid) or with very strong nitric acid, specific gravity 1.52. If the trihydric alcohol has been purified before nitration, there is but little tendency for the nitrate to form emulsions during the washing, and the operation is carried out in the same way as with nitroglycerin. In the laboratory preparation, the nitric ester is taken up in ether, neutralized with ammonium carbonate, dried with anhydrous sodium sulfate, and freed from solvent in a vacuum desiccator. The explosive is procured as a yellow oil, more viscous than nitroglycerin, density 1.68 at ordinary temperature. It has but little tendency to crystallize at low temperatures. A freezing point of —35° has been reported. It is very readily soluble in ether and in acetone, readily soluble in alcohol, in benzene, and in chloroform, and insoluble in ligroin. It is less soluble in water and less volatile than nitroglycerin. Because it is less volatile, it is slower to cause headaches, and for the same reason the headaches are slower to go away. It is distinctly inferior to nitroglycerin as a gelatinizing agent for collodion nitrocotton. The nitro group attached directly to an aliphatic carbon atom appears to have an unfavorable effect on stability, for trimethylol-
NITROPENTANONE AND RELATED SUBSTANCES 285 nitroniethane trinitrate gives a poorer potassium iodide 65.5° heat test than nitroglycerin. Naoum 120 reports the data which arc tabulated below. TBIMETHTLOL- N1TB0METHANE NlTBO- TBINlTIMTt' GLYCKR13J Trauzl test: 75% kieselguhr dynamite 325 cc. 305 cc. 93% blasting gelatin 580 cc. 600 cc. Drop test, 2-kilogram weight . 6 cin. 2 cm. Nitropentanone and Related Substances Cyclopentanone and cyclohexanone contain four active hydrogen atoms and condense with formaldehyde to form substances which contain four —CH2—OH groups. The latter may be converted directly into explosive tetranitrates or they may be reduced, the carbonyl groups yielding secondary alcohol groups, and the products then may be nitrated to pentanitrates. CH, CH, C=0 *CHS c: CH, /CH-OH "CH2-OH c=o — ,CH2-0H "CHj-OH -CHj-OH "CH-OH CH-OH -CH-OH CH, C C=O .CH,-0N0, CH-ONO, Tetramethylolcyclopentanone tetranltrate CH2 CH, .CH2-ONO2 CH-ONOj / .CH^-ONOj Tetraiuethylolcyclopelitanol pentaultrate The explosives derived in this way from cyclopentanone and cyclohexanone were patented in 1929 by Friederich and Flick. 1 - 1 They 120 Op. cit., p. 241. 121 Ger. Pat. 509,118 (1929).
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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
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STARS 81 the space between the star
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STARS 83 4-ply manila paper tubing,
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STARS 85 YVeingart 31 reports compo
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STARS 87 powder mixture, given a ye
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GERBS 89 Gerbs Gerbs produce jets o
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WHEELS 91 denly with a terrifying r
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PINWHEELS 93 Pinwheels To make pinw
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PINWHLELS 95 need of a vast theater
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MINES 97 match or fire wick), for t
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COMETS AND METEORS 99 an electric o
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BOMBSHELLS 101 the short pieces sep
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BOMBSHELLS 103 is folded, rubbed, a
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TOY CAPS 105 "It is to be noted," h
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JAPANESE TORPEDOES 107 minate but w
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RAILWAY TORPEDOES 109 hardens it),
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CHINESE FIRECRACKERS 111 English Cr
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CHINESE FIRECRACKERS 113 carrying o
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CHINESE FIRECRACKERS 115 struck a s
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SPARKLERS 117 is shaped by a motion
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PHARAOH'S SERPENTS 119 Wire Dips an
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BLACK NON-MERCURY SNAKES 121 pellet
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Potassium chlorate Lactose Paranitr
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CHAPTER IV AROMATIC NITRO COMPOUNDS
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EFFECT OF GROUPS ON FURTHER SUBSTIT
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UTILIZATION OF COAL TAR 129 the nuc
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UTILIZATION OF COAL TAR 131 In each
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MONO- AND DI-NITROBENZENE 133 Trini
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TRINITROBENZENE 135 powder, 250 lit
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TRINITROBENZENE 137 + CHsONo H. ,OC
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TRINITROBENZENE 139 According to Da
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TRINITROTOLUENE 141 not yet been de
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TRINITROTOLUENE 143 ?mall amount, p
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TRINITROTOLUENE 145 with a correspo
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TRINITROTOLUENE 14? The soluble sul
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TRINITROTOLUENE 149 cent free SOa)
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TRINITROTOLUENE 151 CH, NO, " ~" a
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TRIXITROXYLENE 153 Dautriche found
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NITRO DERIVATIVES OF NAPHTHALENE I5
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NITRO DERIVATIVES OF NAPHTHALENE 15
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PICRIC ACID 159 of biphenyl. The mo
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PICRIC ACID 161 dinitrophenol as re
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PICRIC ACID 163 a yellow nitropheno
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PICRIC ACID 165 below have been pub
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AMMONIUM PICRATE 167 80° and 90°
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TR1NITR0ANIS0L AND TRINITROPHENETOL
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TRINITROANISOL AND TRINITROPHENETOL
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TETRANITROANILINE 173 Both trinitro
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TETRYL 175 TNA shows about the same
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TETRYL 177 All the above-indicated
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TETRYL 179 m-nitrotetryl is effecti
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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
Page 233 and 234: TRIMETHYLENE GLYCOL DINITRATE 233 i
Page 235 and 236: Butylene Glycol Dinitrate NITROERYT
Page 237 and 238: NITROMANNITE 23? While its stabilit
Page 239 and 240: NITRATED SUGAR MIXTURES 239 fact th
Page 241 and 242: NITROLACTOSE 241 Nitroglucose (d-Gl
Page 243 and 244: OTHER NITROSUGARS 243 readily solub
Page 245 and 246: EARLY HISTORY OF NITRATED CARBOHYDR
Page 257 and 258: NITROCELLULOSE 257 The two substanc
Page 259 and 260: NITROCELLULOSE 259 dre B. Either CP
Page 261 and 262: NITROCELLULOSE 261 nent materials w
Page 263 and 264: NltfROCELLULOSE 263 The pulped fibe
Page 265 and 266: NITROCELLULOSE 265 cellulose with g
Page 267 and 268: DURATION AT 1st period 2nd period 3
Page 269 and 270: DETERMINATION OF NITROGEN 269 upon
Page 271 and 272: DETERMINATION OF NITROGEN 271 actio
Page 273 and 274: NITROSTARCH 273 At the beginning of
Page 275 and 276: NJTROSTARCH 275 the contents of the
Page 277 and 278: UTILIZATION OF FORMALDEHYDE 277 cat
Page 279 and 280: PENTAERYTHRITE TETRANITRATE 279 ery
Page 281 and 282: DIPENTAERYTHRITE HEXANITRATE 281 ni
Page 283: TRIMETHYLOLNITROMETHANE TRINITRATE
Page 287 and 288: CHAPTER VI SMOKELESS POWDER An acco
Page 289 and 290: BULK POWDER 289 was called E C. pow
Page 291 and 292: BULK POWDER 291 FIGURE 71. Sweetie
Page 293 and 294: EARLY HISTORY OF COLLOIDED POWDERS
Page 295 and 296: EARLY HISTORY OF COLLOIDED POWDERS
Page 297 and 298: COLLOIDED NITROCELLULOSE POWDERS 29
Page 299 and 300: MANUFACTURE OF SINGLE-BASE POWDER 2
Page 307 and 308: STABILIZERS 307 Stabilizers The spo
Page 309 and 310: STABILIZERS 309 stable as those con
Page 311 and 312: TRANSFORMATIONS DURING AGING OF POW
Page 313 and 314: ABSORPTION OF MOISTURE 313 ence is
Page 315 and 316: ABSORPTION OF MOISTURE 315 ences. E
Page 317 and 318: CONTROL OF RATE OF BURNING 317 GAIN
Page 319 and 320: CONTROL OF RATE OF BURNING 319 Prog
Page 321 and 322: GELATINIZING AGENTS 321 but very li
Page 323 and 324: FLASHLESS CHARGES AND FLASHLESS POW
Page 329 and 330: BALL-GRAIN POWDER 329 in the presen
Page 331 and 332: CHAPTER VII DYNAMITE AND OTHER HIGH
Page 333 and 334: 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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