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326 CHEMISTRY AND TECHNOLOGY OF EXPLOSIVES

V VI

Compound II is highly toxic. It results in the formation of methaemoglobin. The

presence of trinitrotoluene in the human body leads to an enhancement of the

formation of glucuronic acid, which reacts with the alcohols V and VI to form the

corresponding esters.

The formation of the amines III and IV has also been observed by Lamberg

and Callaghan [134].

UNSYMMETRICAL ISOMERS OF TRINITROTOLUENE

The following unsymmetrical trinitro derivatives of toluene are known:

β

2,3,4-

m.p. 112°C

γ

2,4,5-(3,4,6-)

m.p. 104°C

δ

3,4,5-

m.p. 137°C

2,3,5-

m.p. 97.5°C

2,3,6- (2,5,6-)

m. p. 111°C

All isomers are formed by nitration of m- nitrotoluene. Hepp [35] isolated
the β− and γ− isomers from the product of a severe nitration of m- nitrotoluene.

Their structures have been determined by Will [37].
In a number of detailed investigations Marqueyrol, Koehler and Jovinet [135,