Formic anhydride

Preparation

Formic anhydride can be obtained by reaction of formyl fluoride with excess sodium formate and a catalytic amount of formic acid in ether at −78 °C. It can also be produced by reacting formic acid with N,**-dicyclohexylcarbodiimide ((−N=)2C) in ether at −10 °C. It can also be obtained by disproportionation of acetic formic anhydride.

Properties

Formic anhydride is a liquid with boiling point 24 °C at 20 mmHg. Due to its instability, formic anhydride is not commercially available and must be prepared fresh and used promptly.

The decomposition of formic anhydride may be catalyzed by formic acid.

Formic anhydride can be detected in the gas-phase reaction of ozone with ethylene. The molecule is planar in the gas phase.

References

References

1. (2014). "Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)". [[Royal Society of Chemistry.
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4. R. Schijf, J. W. Scheeren, A. van Es, W. Stevens (1965) ''Mixed carboxylic acid anhydrides: IV. formic anhydride''. Recueil des Travaux Chimiques des Pays-Bas, volume 84, issue 5, pages 594–596. {{doi. 10.1002/recl.19650840510
5. Boogaard, A.. (July 1972). "An electron diffraction investigation of the molecular structure of formic anhydride". Elsevier Science.
6. A. Vaccani, A. Bauder and Hs. H. Günthar (1975), ''The Microwave Spectrum of Formic Anhydride''. Abstracts of OSU International Symposium on Molecular Spectroscopy 1970-1979