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434 CHEMISTRY AND TECHNOLOGY OF EXPLOSIVES

EXPLOSIVE PROPERTIES AND APPLICATION OF TRINITRONAPHTHALENE

Trinitronaphthalene is similar to dinitrobenzene as regards its explosive power.

Before and during World War I it was fairly widely used, first in France and later

in Germany, for filling shells, mostly in fusible mixtures with TNT.

Initially it was known as “Naphtite”, later as “Trinal”. Its other names are TN and

TNN.

The maximum rate of detonation of trinitronaphthalene is about 5140 m/sec

(Calvet [32]).

TETRANITRO DERIVATIVES OF NAPHTHALENE

Five isomers of tetranitronaphthalene are known from the literature: the α− isomer,

the position of two nitro groups in it being unknown, the β− (or 1,3,6,8-), the γ−

(1,3,5,8- or 1,4,6,8-), the 6- (1,4,5,8-) and the 1,3,5,7-isomers:

α β γ

m. p. 259°C m. p. 203°C m. p, 194-195°C

δ m. p. 260°C

m. p. 340-345°C decomposition 263-265°C

The isomer δ was originally thought to be 1,2,5,8-tetranitronaphthalene (Will

[17]). This was corrected by Dimroth and Ruck [18a]).

Each of them forms fine sand-coloured crystals, dissolving with difficulty in

organic solvents. Some of them (e.g. 1,3,5,8-) are readily soluble in acetone. Concen-

trated sulphuric and nitric acids are the best solvents for them.

By the nitration of commercial dinitronaphthalene a product is obtained which

consists of the 1,3,6,8-, 1,3,5,8- and 1,4,5,8-isomers. The existence of the α− isomer
is not quite certain. It was reported by d’Aguiar [14], who obtained it by the pro-

longed boiling of 1,5-dinitronaphthalene with nitric acid (sp. gr. 1.45). The exper-

riments were repeated by Beilstein and Kuhlberg [15] with a mixture of nitric and
sulphuric acids instead of the nitric acid alone. However, Will’s investigations [17]