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222 CHEMISTRY AND TECHNOLOGY OF EXPLOSIVES

tween A and B (Buehler et al. [130]). This would explain the superiority of trinitro-

benzene over picric acid as a complex forming agent.

(9) The heat of formation in solution of the addition compound of picric acid

and naphthalene determined by Brönsted [131], using e.m.f. measurements, was

found to be 2.15 kcal/mole. Similar figures were obtained by cryometric measure

Nitromethane

Dinitrodurene

4-acetyl-l-tert.-butyl-3-

-methyl-2,6-dinitrobenzene

1-tert.-butyl -3,5-dimethyl

-2.4,6-trinitrobenzene

Phthalic anhydride

Nitrobenzene

2,6-dinitrotoluene

Maleic anhydride

m-dinitrobenzene

s-trinitrobenzene

“Tetryl” ( N -methyl-2,4,6

N - tetranitroaniline)

Benzoquinone

Tetranitromethane

Chloranil

FIG. 47. Colours of addition products of various nitro compounds with hydrocar-

bons and amines: I - Benzene; II - Xylene; III - Durene; IV - Naphthalene; V -

Acetanilide; VI - Phenanthrene;VII - Tribromoaniline; VIII - Safrole; IX - An-

thracene; X - Aniline; XI - Diphenylamine; XII - Benzidine: XIII -Dimethyl-

aniline (Brackman [126]).

ments (Brown [132]), and solubility measurements (Moore, Shepherd, Goodall

[133]). However, all these measurements have neglected the heat of solution.

Briegleb [114] applied another method which gave more exact figures. He took

advantage of the fact that most of the addition compounds were strongly coloured

and measured the colour change of the solutions with temperature. He found that
the heats of formation of compounds of 1,3,5-trinitrobenzene with various hydro-
carbons in carbon tetrachloride varied between 1.5 and 4.5 kcal/mol.