Trinitromethane

Nitroform

Colorless solid ( below the melting point )

Fixed

1.806 g · cm -1

25.35 ° C

Readily soluble in water

1.4451 ( 24 ° C)

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Trinitromethane is an unstable nitro derivative of the methane and thereby a nitroalkane. The connection is the triply substituted representatives of the series of Nitromethane with nitromethane, dinitromethane, trinitromethane and tetranitromethane.

Production and representation

Trinitromethane was first produced in 1857 in the form of its ammonium salt by Shishkov. In 1918, the synthesis has been developed by the combined oxidation and nitration of ethyne with nitric acid, which allows industrial production. Here, the two reactants are reacted in a tube reactor in the counter flow principle. In the laboratory, it can also be obtained by hydrolysis of tetranitromethane under mild basic conditions. The production by the reaction of nitric acid with isopropyl alcohol is possible. The ammonium salt formed by the action of water or alcohol on Trinitroacetonitril.

Properties

Trinitromethane is a strong acid. The colorless free acid is unstable, the intense yellow anion stable ( NO2) 3C in aqueous solution. For trinitromethane two tautomeric structures can be formulated. The equilibrium lies almost completely on the side of the CH -acidic structure. Quantum chemical calculations show a difference in free energy of 33.0 kJ · mol - 1 for N- OH-acidic structure. 1H -NMR spectrum shows only a single peak at 2.48 ppm for the CH function. In the series of Nitromethane this is the biggest difference compared to methane at 9.767 ppm, 5.72 ppm and nitromethane with dinitromethane at 3.90 ppm.

Use

Trinitromethane is used for the production of explosives and propellants.

Safety

Trinitromethane explodes violently on rapid heating. Solutions with a water content of less than 55 % by mass may still decompose explosively.