Formic anhydride
| Structural formula of formic anhydride | |
| Ball-and-stick model of the formic anhydride molecule | |
| Names | |
|---|---|
| IUPAC name
Formyloxymethanone
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| Other names
Methanoic anhydride
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| Identifiers | |
1558-67-4  |
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| 1901016 | |
| ChEBI | CHEBI:36657 |
| ChemSpider | 7827603 |
| 1041427 | |
| Jmol 3D model | Interactive image |
| PubChem | 9548680 |
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| Properties | |
| C2H2O3 | |
| Molar mass | 74.04 g·mol−1 |
| Appearance | Colorless gas |
| Boiling point | 24 °C (75 °F; 297 K) at 20 mmHg |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Formic anhydride, also called methanoic anhydride, is an organic compound with the chemical formula C
2H
2O
3 and a structural formula of (H(C=O)−)2O. It can be viewed as the anhydride of formic acid (HCOOH).
Contents
Preparation
Formic anhydride can be obtained by reaction of formyl fluoride with sodium formate in ether at −78 °C.[1] It can also be produced by reacting formic acid with N,N′-dicyclohexylcarbodiimide ((C
6H
11−N=)2C) in ether at −10 °C.[2] It can also be obtained by disproportionation of acetic formic anhydride.[3]
Properties
Formic anhydride is a liquid with boiling point 24 °C at 20 mmHg.[2] It is stable in diethyl ether solution. It can be isolated by low-temperature, low-pressure distillation, but decomposes on heating above room temperature.[2] It decomposes into formic acid and carbon monoxide.[4]
The decomposition of formic anhydride may be catalyzed by formic acid.[2]
Formic anhydride can be detected in the gas-phase reaction of ozone with ethylene.[5] The molecule is planar in the gas phase.[2]
See also
References
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<references />, or <references group="..." />- ↑ George A. Olah, Yashwant D. Vankar; Massoud Arvanaghi; Jean Sommer (1979), Formic Anhydride. Angewandte Chemie Int. Ed. Engl., volume 18, issue = 8, page = 614. doi:10.1002/anie.197906141.
- ↑ 2.0 2.1 2.2 2.3 2.4 G. Wu, S. Shlykov, F. S. Van Alseny, H. J. Geise, E. Sluyts, B. J. Van der Veken (1995), Formic Anhydride in the Gas Phase, Studied by Electron Diffraction and Microwave and Infrared Spectroscopy, Supplemented with Ab-Initio Calculations of Geometries and Force Fields. J. Phys. Chem., volume 99, issue 21, pages 8589–8598 doi:10.1021/j100021a022
- ↑ 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
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ 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
