The Chemistry of Powder and Explosives - Sciencemadness Dot Org

150 AROMATIC NITRO COMPOUNDS
MOLECULAR PROPORTIONS M.P. DESCRIPTION
TNT: Substance
1 Aniline 83-84° Long brilliant red needles.
1 Dimethylaniline Violet needles.
1 o-Toluidine 53-55° Light red needles.
1 m-Toluidine 62-63° Light red needles.
1 a-Naphthylamine 141.5° Dark red needles.
1 0-Naphthylamine 113.5° Bright red prismatic needles,
1 0-Acetnaphthalide 106° Yellow needles.
1 Benzyl-0-naphthylamine 106.5° Brilliant crimson needles.
1 Dibenzyl-0-naphthylamine 108° Deep brick-red needles.
1 Benzaldehydephenylhydrazone 84° Dark red needles.
1 2-Methylindole 110° Yellow needles.
2 Carbazole 160° Yellow needles.
1 : 1 Carbazole 140-200° Dark yellow needles.
explodes or inflames when heated to about 230°, but Dupre 32
found that the addition of solid caustic potash to TNT at 160°
caused immediate inflammation or explosion. A mixture of powdered
solid caustic potash and powdered TNT inflames when
heated, either slowly or rapidly, to 80°. A similar mixture with
caustic soda inflames at 80° if heated rapidly, but may be heated
to 200° without taking fire if the heating is slow. If a small
fragment of solid caustic potash is added to melted TNT at 100°,
it becomes coated with a layer of reaction product and nothing
further happens. If a drop of alcohol, in which both TNT and
KOH are soluble, is now added, the material inflames within a
few seconds. Mixtures of TNT with potassium and sodium carbonate
do not ignite when heated suddenly to 100°.
Since the methyl group of TNT is attached to a picryl group,
we should expect it in some respects to resemble the methyl group
of a ketone. Although acetone and other methyl ketones brominate
with great ease, TNT does not brominate and may even be
recrystallized from bromine. The methyl group of TNT, however,
behaves like the methyl group of acetone in certain condensation
reactions. In the presence of sodium carbonate TNT condenses
with p-nitrosodimethylaniline to form the dimethylaminoanilide
of trinitrobenzaldehyde, 33 from which trinitrobenzaldehyde and
N,N-dimethyl-p-diaminobenzene are produced readily by acid
hydrolysis.
82
"Twenty-eighth Annual Report of H. M. Inspector of Explosives," 1903,
p. 26.
83
Sachs and Kempf, Ber., 35, 1222 (1902); Sachs and Everding, ibid.,
36, 999 (1903).