R. Meyer J. Köhler A. Homburg Explosives

309 Tetranitronaphthalene
Tetranitromethane is insoluble in water, but soluble in alcohol and
ether. The volatile compound strongly attacks the lungs. The oxygenrich
derivative is not explosive by itself, but forms highly brisant mixtures
with hydrocarbons such as toluene.
Tetranitromethane is formed as a by-product during nitration of aromatic
hydrocarbons with concentrated acids at high temperatures,
following opening of the ring. It can also be prepared by reacting
acetylene with nitric acid in the presence of mercury nitrate as a
catalyst. According to a more recent method, tetranitromethane is
prepared by introducing a slow stream of ketene into cooled 100%
nitric acid. When the reaction mixture is poured into ice water, tetranitromethane
separates out.
Mixtures of tetranitromethane with organic fuels are very sensitive to
impact and friction and may react spontaneously by detonation or fast
deflagration.
Tetranitronaphthalene
Tetranitronaphthalin; tétranitronaphthaléne; TNN
yellow crystals
empirical formula: C10H4N4O8
molecular weight: 308.2
energy of formation: +23.7 kcal/kg = +99.2 kJ/kg
enthalpy of formation: +8.4 kcal/kg = +35.3 kJ/kg
oxygen balance: –72.7%
nitrogen balance: 18.18%
melting point:
softening of the isomer mixture
begins at 190 °C = 374 °F
Tetranitronaphthalene is a mixture of isomers, which is obtained by
continued nitration of dinitronaphthalenes.
The tetrasubstituted compound can only be attained with difficulty. The
crude product is impure and has an irregular appearance. It can be
purified with glacial acetic acid.