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Tetranitromethane

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Tetranitromethane

Tetranitromethane[1]
Identifiers
CAS number  YesY
ChemSpider  YesY
UN number 1510
KEGG  N
ChEMBL  YesY
RTECS number PB4025000
Jmol-3D images Image 1
Properties
Molecular formula CN4O8
Molar mass 196.04 g/mol
Appearance Colorless to pale-yellow liquid or solid
Odor Pungent
Density 1.623 g/cm3
Melting point 13.8 °C (56.8 °F; 287.0 K)
Boiling point 126 °C (259 °F; 399 K)
Hazards
MSDS ICSC 1468
EU Index Not listed
EU classification Oxidizing Agent O Toxic T
R-phrases R8 R23/24/25 R36/38 R45
S-phrases S17 S45
Main hazards Oxidant, can form explosive mixtures
NFPA 704
1
3
2
OX
Related compounds
Related compounds Hexanitroethane
Octanitropentane
Trinitromethane
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N   YesY/N?)

Tetranitromethane or TNM is an 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 cetane number.[4]

Preparation

TNM is a pale yellow liquid that can be prepared in the laboratory by the nitration of acetic anhydride with anhydrous nitric acid (Chattaway's method).[5] This method was attempted on an industrial scale in the 1950s by Nitroform Products Company in Newark, USA, but the entire plant was destroyed by an explosion in 1953.[6]

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.[7] 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.[8]

For commercial use a cheaper method starting from acetylene has been used.[9] First, nitric acid containing mercuric nitrate is reduced by acetylene, resulting in nitroform (trinitromethane) and a mixture of carbon dioxide and nitrogen oxide as waste gas. The nitrogen oxides are valuable and normally recovered as nitric acid in an absorption tower. The resulting nitroform is converted to TNM by adding nitric and sulfuric acid at higher temperatures. With this method a yield of 90% (based on nitric acid) before purification can be reached.[10]

Safety

The ability of TNM to detonate is greatly affected by the presence of impurities, even in small quantities. TNM forms extremely powerful explosive mixtures when fuels are added in stoichiometric proportions. Many of these mixtures show sensitivity to impact even higher than that of nitroglycerine.[11]

TNM reacts with moisture at elevated pH to produce trinitromethane (nitroform) which reacts easily with metals to form highly unstable and explosive salts.

Tetranitromethane is highly toxic. Absorption of as little as 2.5 mg/kg can cause methemoglobinemia, lung edema, and damage to liver, kidney, and central nervous system. It is reasonably expected to be a human carcinogen.[12]

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".  
  3. ^ J. G. Tschinkel (1956). "Tetranitromethane as Oxidizer in Rocket Propellants".  
  4. ^ K. V. Altukhov, V. V. Perekalin (1976). "The Chemistry of Tetranitromethane". Russian Chemical Reviews 45 (11): 1052–1066.  
  5. ^ Liang, P. (1941), "Tetranitromethane",  
  6. ^ Mahoney vs Nitroform Co., 114 A.2d 863 (NJ Appellate Div 1955).
  7. ^ F. D. Chattaway (1910). "A simple method of preparing tetranitromethane".  
  8. ^ K. F. Hager (1949). "Tetranitromethane".  
  9. ^ K. J. P. Orton, P. V. McKie (1920). "The action of nitric acid on unsaturated hydrocarbons. The action of nitric acid on acetylene".  
  10. ^ Urbanski, Tadeusz (1964). Chemistry and Technology of Explosives I. Pergamon Press. pp. 589–594.  
  11. ^ Urbanski, Tadeusz (1964). Chemistry and Technology of Explosives I. Pergamon Press. p. 593.  
  12. ^  

External links

  • WebBook page for CN4O8
  • CDC - NIOSH Pocket Guide to Chemical Hazards
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