The Chemistry of Powder and Explosives - Sciencemadness Dot Org

TRINITROTOLUENE 14?
The soluble sulfonates in the deep red solution, if they are thrown
into the sewer, represent a loss of about 4 per cent of all the
toluene—a serious loss in time of war—as well as a loss of many
pounds of nitro group nitrogen. The sulfonic acid group in these
substances, like the nitro group which it replaced, is ortho, or
ortho and para, to two nitro groups, and is active and still capable
of undergoing the same reactions as the original nitro group.
They may be converted into a useful explosive by reaction with
methylamine and the subsequent nitration of the resulting dinitrotolylmethylamines,
both of which yield 2,4,6-trinitrotolyl-3methylnitramine
or m-methyltetryl.
CH;
CH,
?n-Methyltetryl, pale yellow, almost white, crystals from alcohol,
m.p. 102°, was prepared in 1884 by van Romburgh 27 by the nitration
of dimethyl-m-toluidine, and its structure was demonstrated
fully in 1902 by Blanksma, 28 who prepared it by the synthesis
indicated on the next page.
/?- and y-TNT lose their active nitro group by the action of
aqueous alkali and yield salts of dinitro-m-cresol. 29 The mixed
dinitro-m-cresols which result may be nitrated to trinitro-mcresol,
a valuable explosive. Their salts, like the picrates, are
primary explosives and sources of danger. 0- and y-TNT react
with lead oxide in alcohol to form lead dinitrocresolates, while
a-TNT under the same conditions remains unaffected.
In plant-scale manufacture, TNT is generally prepared by a
27 Rec. trav. chim., 3, 414 (1884).
28 Ibid., 21, 327 (1902).
29 Will, Ber., 47, 711 (1914); Copisarow, Chem. News, 112, 283 (1915).