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Ethylene carbonate

Ethylene carbonate
Skeletal formula of ethylene carbonate
Ball-and-stick model of the ethylene carbonate molecule
Names
IUPAC name
1,3-dioxolan-2-one
Other names
ethylene glycol carbonate
Identifiers
96-49-1 YesY
3D model (Jmol) Interactive image
ChemSpider 7030 YesY
ECHA InfoCard 100.002.283
PubChem 7303
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
Hazards
Safety data sheet External MSDS
Irritant (XI)
R-phrases R41
S-phrases S26 S39
Flash point 150 °C (302 °F; 423 K)
465 °C (869 °F; 738 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
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.

Ethylene carbonate is produced by the reaction between ethylene oxide and carbon dioxide. The reaction is catalyzed by a variety of cations and complexes:

Ethylene carbonate (and propylene carbonate) may be converted to dimethyl carbonate (a useful solvent and a mild methylating agent) via transesterification by methanol:

Dimethyl carbonate may itself be similarly transesterified to diphenyl carbonate, a phosgene-substitute:

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.


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