Rahul Sharma (Editor)

Ethylene carbonate

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Density
  
1.32 g/cm³

Appearance
  
White to yellow solid

Formula
  
C3H4O3

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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.

Contents

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:

(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:

CH3OCO2CH3 + 2 PhOH → PhOCO2Ph + 2 MeOH

Applications

Ethylene carbonate is used as a polar solvent with a molecular dipole moment of 4.9 D, 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.

References

Ethylene carbonate Wikipedia


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