Ethylene carbonate
| Ethylene carbonate | |
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1,3-dioxolan-2-one |
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Other names
ethylene glycol carbonate[1] |
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| Identifiers | |
| CAS number | 96-49-1  |
| PubChem | 7303 |
| ChemSpider | 7030 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C3H4O3 |
| Molar mass | 88.06 g mol−1 |
| Appearance | White to yellow solid |
| Density | 1.3210 g/cm3 |
| Melting point |
34-37 °C, 307-310 K, 93-99 °F |
| Boiling point |
260.7 °C, 534 K, 501 °F |
| Solubility in water | Soluble |
| Hazards | |
| MSDS | External MSDS |
| EU classification | Irritant (XI) |
| R-phrases | R41 |
| S-phrases | S26 S39 |
| Flash point | 150 °C (302 °F) |
| Autoignition temperature |
465 °C (869 °F) |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Ethylene carbonate is a 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]
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[edit] Production
Ethylene carbonate is produced by the reaction between ethylene oxide and carbon dioxide.
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
[edit] 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.
[edit] See also
[edit] External links
[edit] References
- ^ "CID 7303 -- PubChem Compound Summary". pubchem.ncbi.nlm.nih.gov. Retrieved 2008-03-15.
- ^ JEFFSOL ETHYLENE CARBONATE catalog entry at www.huntsman.com. Accessed on 2010-02-18.
- ^ Hans-Josef Buysch (2005), "Carbonic Esters", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a05_197
- ^ Ralph P. Seward; Ernest C. Vieira (1958). "The Dielectric Constants of Ethylene Carbonate and of Solutions of Ethylene Carbonate in Water, Methanol, Benzene and Propylene Carbonate". J. Phys. Chem. 62 (1): 127–128. Text "10.1021/j150559a041" ignored (help)
- ^ Richard Payne; Ignatius E. Theodorou (1972). "Dielectric properties and relaxation in ethylene carbonate and propylene carbonate". J. Phys. Chem. 76 (20): 2892–2900. doi:10.1021/j100664a019.
