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252 CHEMISTRY AND TECHNOLOGY OF EXPLOSIVES

It seems possible that the products of the reaction of sym-trinitrobenzene with

NaOH or alkali ethoxides are not individuals but mixtures of several compounds.

For example, Busch and Kögel [41] found that sym-trinitrobenzene was able to

add on not only one, but also two or three molecules of an ethoxide.

Trinitrobenzene combines with potassium cyanide to form a blood red addition

product, to which Meisenheimer [40] ascribed the structure:

Oxidation. Mild oxidizing agents, such as potassium ferricyanide, convert tri-

nitrobenzene into picric acid (p. 204).

Reduction. sym-Trinitrobenzcne, when reduced with sodium- or ammonium

sulphide, forms 3,5-dinitroaniline. By treating it with hydrogen sulphide in alcoholic

solution dinitrophenylhydroxylamine may be formed:

(12)

With sodium polysulphide, sym-trinitrobenzene yields tetranitroazoxybenzene

along with dinitroaniline. All three nitro groups can be reduced by tin or iron

in hydrochloric acid, triaminobenzenc being formed, which is the starting material

for the manufacture of phloroglucinol. sym-Trinitrobenzene can react with sodium

borohydride to yield trinitrocyclohexane (Severin [66]).

Reaction specific to sym-trinitrobenzene. Sym-trinitrobenzene in acetone solu-

tion rapidly produces a red colour with alkali hydroxides or ammonia. In the

absence of the solvent the colour develops slowly.

Addition compounds. sym-Trinitrobenzcne readily forms well defined, often

coloured compounds with hydrocarbons with condensed rings. Kremann and

co-workers [18,44], Jefremov and co-workers [9,11,44a], Sudborough and Beard

[44b] and their co-workers have studied most of these systems, containing sym-

trinitrobenzene, by thermal analysis.