Ethylene carbonate
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| Names | |||
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| IUPAC name
1,3-dioxolan-2-one
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| Other names
ethylene glycol carbonate[1]
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| Identifiers | |||
96-49-1  |
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| ChemSpider | 7030 |
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| Jmol 3D model | Interactive image | ||
| PubChem | 7303 | ||
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| Properties | |||
| C3H4O3 | |||
| Molar mass | 88.06 g·mol−1 | ||
| Appearance | White to yellow solid | ||
| Density | 1.3210 g/cm3 | ||
| Melting point | 34 to 37 °C (93 to 99 °F; 307 to 310 K) | ||
| Boiling point | 243.0 °C (469.4 °F; 516.1 K) | ||
| Soluble | |||
| Vapor pressure | {{{value}}} | ||
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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 | |||
Ethylene carbonate is the organic compound with the formula (CH2O)2CO. It is classified as the carbonate ester of ethylene glycol and carbonic acid. At room temperature (25 °C) ethylene carbonate is a transparent crystalline solid, practically odorless and colorless, and somewhat soluble in water. In the liquid state (m.p. 34-37 °C) it is a colorless odorless liquid.[2]
Production and reactions
Ethylene carbonate is produced by the reaction between ethylene oxide and carbon dioxide. The reaction is catalyzed by a variety of cations and complexes:[3]
- (CH2)2O + CO2 → (CH2O)2CO
Ethylene carbonate (and propylene carbonate) may be converted to dimethyl carbonate (a useful solvent and a mild methylating agent) via transesterification by methanol:
- C2H4CO3 + 2 CH3OH → CH3OCO2CH3 + HOC2H4OH
Dimethyl carbonate may itself be similarly transesterified to diphenyl carbonate, a phosgene-substitute:[3]
- CH3OCO2CH3 + 2 PhOH → PhOCO2Ph + 2 MeOH
Applications
Ethylene carbonate is used as a polar solvent with a molecular dipole moment of 4.9 D,[4][5] only 0.1 D lower than that of propylene carbonate. It can be used as a high permittivity component of electrolytes in lithium batteries.
Ethylene carbonate is also used as plasticizer, and as a precursor to vinylene carbonate, which is used in polymers and in organic synthesis.
See also
External links
References
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ JEFFSOL ETHYLENE CARBONATE catalog entry at www.huntsman.com. Accessed on 2010-02-18.
- ↑ 3.0 3.1 Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
