TNT: Trinitrotoluenes and Mono and Dinitrotoluenes

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and THE THEORETICAL NITRATION OF TOLUENE 21 2) +H2SO4 C6H3(CH3)(NO2)(SO3H) +HNO3 -* C6H3(CH3)(NO2)(SO3H) +H2O, The third-stage reaction is similar to the second stage: C6H3(CH3) (NO2)2 +H2SO4 and C6H2(CH3)(NO2)2(SO3H) +HNO3 -* C6H2(CH3)(NO2)2(SO3H) +H2O, -> C6H2(CH3) (NO2)3 +H2SO4. In each stage there may be the reactions of either previous or later stages taking place, because of the impossibility of absolute control. The theory that sulphonation takes place before the nitration can be accomplished may be the key to the question as to why some mono- and dinitrotoluenes are easily nitrated, and some are difficultly nitrated. The sulphonic group follows the laws of orientation perhaps more closely than almost any other group, and this explains why (assuming the sulphonation theory) dilute nitric acid will not nitrate direct, but will merely replace a sulphonic group. Therefore, if the sulphonic group is not already in place, the nitrogroup cannot enter the molecule. So, if the previous
22 TRINITROTOLUENE stage has resulted in the formation of isome^ with the groups in such positions that the sulphonic group cannot enter the molecule easily, the isomer will be nitrated only by very strong nitric acid, or by using some special method of introducing the sulphonic group. This solution to the question would seem to indicate that in the first-stage nitration the sulphonation does not take place, but that the toluene is nitrated directly by the use of nitric acid. Starting with toluene, purified as is considered necessary for nitrations, the primary nitration is to mononitrotoluene. The theoretically perfect nitration would proceed in this manner: CH3 CH3 CH3 CH3 NO2 This nitration, however, is never accomplished, for the mononitrotoluene consists of all three isomeric forms. The mononitrotoluene modifications are present in the proportion of 38 per cent para, 60 per cent ortho, and 2 to 4 per cent meta. (1) This result is exactly what would be expected, because with the methyl group in position 1, the tendency of the nitro-groups is to enter either position 2 or position 4. This fact holds true even with the more generally accepted view that the first stage of the reaction consists in sulphonating the toluene, because the sulphonic group behaves and orientates just the same as the nitro-group, and with the methyl group in position 1, the sulphonic group will also enter either position 2 or position 4. The
Page 1 and 2: T N T rri r R r N I T E O T O L U E
Page 3 and 4: WHOSE SACRIFICES AND LOVE HAVE MADE
Page 5 and 6: TABLE OF CONTENTS CHAPTER I PAGE IN
Page 7 and 8: 2 TRINITROTOLUENE use in specificat
Page 9 and 10: 4 TRINITROTOLUENE On the other hand
Page 11 and 12: CHAPTER II HISTORICAL SOME doubt ex
Page 13 and 14: 8 TRINITROTOLUENE ter's work, isola
Page 15 and 16: 10 TRINITROTOLUENE uene was identif
Page 17 and 18: 12 TRINITROTOLUENE toluene is nothi
Page 19 and 20: 14 TRINITROTOLUENE Ortho Meta Para
Page 21 and 22: 16 TEINITROTOLUENE obtained; the or
Page 23 and 24: 18 TRINITROTOLUENE proved it to be
Page 25: CHAPTER III THE THEORETICAL NITRATI
Page 29 and 30: 24 TRINITROTOLUENE another nitro-gr
Page 31 and 32: 26 TRINITROTOLUENE (The German theo
Page 33 and 34: 28 TRINITROTOLUENE ' the small amou
Page 35 and 36: 30 TRINITROTOLUENE responds instant
Page 37 and 38: 32 TRINITROTOLUENE in the manufactu
Page 39 and 40: 34 TRINITROTOLUENE This principle o
Page 41 and 42: 36 TRINITROTOLUENE such that the wa
Page 43 and 44: 38 TRINITROTOLUENE 2.2. The total a
Page 45 and 46: 40 TRINITROTOLUENE tion of the high
Page 47 and 48: 42 TRINITROTOLUENE Following the ni
Page 49 and 50: 44 TRINITROTOLUENE have been used w
Page 51 and 52: 46 TRINITROTOLUENE This is necessar
Page 53 and 54: 48 TRINITROTOLUENE granted in 1914,
Page 55 and 56: 50 TRINITROTOLUENE good plan to ove
Page 57 and 58: CHAPTER V THE PURIFICATION OF TNT T
Page 59 and 60: 54 TRINITROTOLUENE with the top of
Page 61 and 62: 56 TRINITROTOLUENE has been added,
Page 63 and 64: 58 TRINITROTOLUENE 6. Modified Solv
Page 65 and 66: 60 TRINITROTOLUENE to the decomposi
Page 67 and 68: 62 TRINITROTOLUENE and the samples
Page 69 and 70: 64 TRINITROTOLUENE cent alcohol, co
Page 71 and 72: 66 TRINITROTOLUENE Care must be tak
Page 73 and 74: 68 TRINITROTOLUENE this it will sol
Page 75 and 76: 70 TRINITROTOLUENE This last is the
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72 TRINITROTOLUENE gible. The adopt
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74 TRINITROTOLUENE Na2O No. 1. Na2S
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76 TRINITROTOLUENE pressed into pla
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78 TRINITROTOLUENE governed almost
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80 TRINITROTOLUENE The complete tab
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82 TRINITROTOLUENE ting off the car
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84 TRINITROTOLUENE Dimethylaniline
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86 TRINITROTOLUENE trinitrotoluene
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88 TRINITROTOLUENE the stilbenes ar
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90 TRINITROTOLUENE reaction of expl
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92 TRINITROTOLUENE In his report, h
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94 TRINITROTOLUENE The density of T
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96 TRINITROTOLUENE tion. Extended r
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Jill X JTROTOLITXE v.i!.-. A mui-h
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TIJIMTRUTOLUEXE *>.», r.i* ;rv u "
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1 u-2 TRINITROTOLUENE The Dinitroto
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104 TRINITROTOLUENE as thoroughly a
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CHAPTER IX ACCIDENTS TXT is conside
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1 OS TRINITROTOLUEXE A metallic con
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110 TRIXITROTOIXEKE The workman, im
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CHAPTER X TNT DISEASES THE problem
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114 TRIXITROTOIXEXE then mixed with
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116 TRINITROTOLUENE There are six d
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11 N TRINITROTOLUENE actual increas
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REFERENCES CHAPTER II (1) Anallen,
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REFERENCES 123 >n. Chem. Soc, 1903,
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126 INDEX FAGH Boiling-point of the
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128 INDEX PAGE Grainer 45 Graining
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130 INDEX P Packing PAGE 61 Para ni
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132 INDEX PAGE Toluene detection of
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TNT: Trinitrotoluenes and Mono and Dinitrotoluenes

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