Tetranitromethane

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Tetranitromethane[1]
File:Tetranitromethane.pngFile:Tetranitromethane 3D.png
Chemical name Tetranitromethane
Other names TNM
Tetan
Chemical formula CN4O8
Molecular mass 196.04 g/mol
CAS number [509-14-8]
Density 1.623 g/cm3
Melting point 13.8 °C
Boiling point 126 °C
SMILES O=[N+]([O-])C([N+]([O-])=O)([N+]([O-])=O)[N+]([O-])=O
Disclaimer and references

Tetranitromethane or TNM is an organic oxidizer with chemical formula C(NO2)4. Its chemical structure consists of four nitro groups attached to one carbon atom. In 1857 it was first synthesised by the reaction of sodium cyanoacetamide with nitric acid. [2]

Uses

It has been investigated for use as an oxidizer in bipropellant rockets, however its extreme explosive sensitivity makes it effectively unusable.[3] In the laboratory it is used a reagent for the detection of double bonds in organic compounds and as a nitrating reagent. It has also found use as an additive to fuel to increase the cetane number. [4]

Preparation

TNM is a pale yellow liquid that can be prepared by the nitration of acetic anhydride with anhydrous nitric acid.[5]

The first industrial scale production was started in Germany during World War II in an effort to improve the cetane number of diesel fuel. This process improved the original method, which started with acetic acid and nitric acid. [6]. Without regard to yield or cost, approximately 10 tons of TNM were produced in a few weeks. However, this production process has not been used again industrially after the end of the war, because of high associated costs. [7]

For commercial use a cheaper method starting from acetylene has been used. [8] First, acetylene is reacted with nitric acid containing mercury nitrate, resulting in nitroform (trinitromethane) and a mixture of carbon dioxide and nitrogen oxide as waste gas. The resulting nitroform is converted to TNM by adding sulfuric acid at higher temperatures. With this method a yield of 90% before purification can be reached.

References

  1. Merck Index, 11th Edition, 9164.
  2. L. N. Shishkov (1857). "Sur la constitution de l'acetic fulminique et un nouvelle serie de corps derives de l'acide acetique". Annales de chimie et de physique. 49 (11): 310.
  3. J. G. Tschinkel (1956). "Tetranitromethane as Oxidizer in Rocket Propellants". Industrial and Engineering Chemistry. 48 (4): 732. doi:10.1021/ie50556a022.
  4. K. V. Altukhov, V. V. Perekalin (1976). "The Chemistry of Tetranitromethane". Russian Chemical Reviews. 45 (11): 1052–1066. doi:10.1070/RC1976v045n11ABEH002759.
  5. Org. Syn. Coll. Vol. III, 1955, 803.
  6. F. D. Chattaway (1910). "A simple method of preparing tetranitromethane". Journal of the Chemical Society. 97: 2099–2102. doi:10.1039/CT9109702099.
  7. K. F. Hager (1949). "Tetranitromethane". Industrial and Engineering Chemistry. 41 (10): 2168–2172. doi:10.1021/ie50478a028.
  8. K. J. P. Orton, P. V. McKie (1920). "The action of nitric acid on unsaturated hydrocarbons. The action of nitric acid on acetylene". Journal of the Chemical Society. 117: 283–297. doi:10.1039/CT9201700283.

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