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Ethylene carbonate

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Title: Ethylene carbonate  
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Ethylene carbonate

Ethylene carbonate
Skeletal formula Ball-and-stick model
Identifiers
CAS number  YesY
PubChem
ChemSpider  YesY
Jmol-3D images Image 1
Properties
Molecular formula 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 260.7 °C (501.3 °F; 533.8 K)
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; 423 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY   YesY/N?)

Ethylene carbonate is 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]

Contents

  • Production and reactions 1
  • Applications 2
  • See also 3
  • External links 4
  • References 5

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 organic synthesis.

See also

External links

  • WebBook page for ethylene carbonate

References

  1. ^ "CID 7303 -- PubChem Compound Summary". pubchem.ncbi.nlm.nih.gov. Retrieved 2008-03-15. 
  2. ^ JEFFSOL ETHYLENE CARBONATE catalog entry at www.huntsman.com. Accessed on 2010-02-18.
  3. ^ a b Hans-Josef Buysch (2005), "Carbonic Esters",  
  4. ^ 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.  
  5. ^ Richard Payne; Ignatius E. Theodorou (1972). "Dielectric properties and relaxation in ethylene carbonate and propylene carbonate". J. Phys. Chem. 76 (20): 2892–2900.  
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