The Chemistry of Powder and Explosives - Sciencemadness Dot Org

174 AROMATIC NITRO COMPOUNDS
NO, NH, NH,
j-NO, NO,
NO,
Pure TNA, yellowish-brown or greenish-brown crystals from
acetone, melts with decomposition at about 210° and deflagrates
at about 226°. It is soluble in glacial acetic acid (1 part in 24 at
boiling temperature), readily in acetone (1 in 6 at boiling temperature),
and sparingly in benzene, ligroin, and chloroform. If
a small amount of water is added to an acetone solution of TNA
and the liquid is refluxed, the nitro group in the 3-position, having
other nitro groups ortho and para to it, is replaced rapidly
by hydroxyl. The resulting trinitroaminophenol, m.p. 176°, is
capable of attacking metals to form dangerous explosive salts
which are similar to the picrates. If TNA is boiled with aqueous
sodium carbonate or bicarbonate both the amino group and the
nitro group in the 3-position are hydrolyzed, and trinitroresorcinol
is formed.
NH: NH, NH,
NO,H,ONO
•NO,
NO2alk. HH.0
•NO,
NO2 NH2 NO,
With alcoholic ammonia TNA yields trinitro-m-phenylenediamine,
m.p. 288°. Its nitro group in the 3-position reacts with
primary and secondary amines, with sodium acid sulfite, etc., in
the same way that the meta nitro groups of /3- and -y-trinitrotoluene
do. Marqueyrol found that TNA is attacked rapidly by
boiling water, about half of it being converted into trinitroaminophenol,
the other half being destroyed with the evolution
of gases, largely carbon dioxide and nitrogen along with smaller
quantities of carbon monoxide, hydrocyanic acid, and nitric oxide.
At 75° the reaction between water and TNA is complete after
4 days; at 60° it is about half complete after 7 days; at 40° it is
appreciable after 10 days. Any decomposition of this sort, of
course, is too much for an explosive intended for military use.