Tetranitromethane

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Tetranitromethane[1]
IUPAC name Tetranitromethane
Other names TNM
Tetan
Identifiers
CAS number [509-14-8]
SMILES O=[N+]([O-])C([N+]([O-])=O)([N+]([O-])=O)[N+]([O-])=O
Properties
Molecular formula CN4O8
Molar mass 196.04 g/mol
Density 1.623 g/cm3
Melting point

13.8 °C
Boiling point

126 °C
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox 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]

Contents

[edit] Uses

It has been investigated for use as an oxidizer in bipropellant rockets, however its high freezing temperature makes it unsuitable. The explosive sensitivity is low, but would be raised by anti-freezing additives. This 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]

[edit] 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.[7]

[edit] 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. ^ a b 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. 

[edit] External links