Formic anhydride
Chemical compound From Wikipedia, the free encyclopedia
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).
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| Names | |
|---|---|
| Preferred IUPAC name
Formic anhydride[1] | |
| Other names
Methanoic anhydride Formyloxymethanone | |
| Identifiers | |
3D model (JSmol) |
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| 1901016 | |
| ChEBI | |
| ChemSpider | |
| 1041427 | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C2H2O3 | |
| Molar mass | 74.035 g·mol−1 |
| Appearance | Colorless gas |
| Boiling point | 24 °C (75 °F; 297 K) at 20 mmHg |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[2] It can also be produced by reacting formic acid with N,N′-dicyclohexylcarbodiimide ((C
6H
11−N=)2C) in ether at −10 °C.[3] It can also be obtained by disproportionation of acetic formic anhydride.[4]
Properties
Formic anhydride is a liquid with boiling point 24 °C at 20 mmHg.[3] It is stable in diethyl ether solution. It can be isolated by low-temperature, low-pressure distillation, but decomposes on heating above room temperature.[3] At room temperature and higher, it decomposes through a decarbonylation reaction into formic acid and carbon monoxide.[5] 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.[3]
Formic anhydride can be detected in the gas-phase reaction of ozone with ethylene.[6] The molecule is planar in the gas phase.[3]
See also
References
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