Ethylene carbonate

Ethylene carbonate

Names
IUPAC name 1,3-dioxolan-2-one
Other names ethylene glycol carbonate[1]
Identifiers
CAS Number	96-49-1
ChemSpider	7030
Jmol interactive 3D	Image
PubChem	7303
InChI InChI=1S/C3H4O3/c4-3-5-1-2-6-3/h1-2H2 Key: KMTRUDSVKNLOMY-UHFFFAOYSA-N InChI=1/C3H4O3/c4-3-5-1-2-6-3/h1-2H2 Key: KMTRUDSVKNLOMY-UHFFFAOYAD
SMILES C1COC(=O)O1
Properties
Chemical formula	C3H4O3
Molar mass	88.06 g·mol^−1
Appearance	White to yellow solid
Density	1.3210 g/cm^3
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)
Solubility in water	Soluble
Hazards
Safety data sheet	External MSDS
EU classification (DSD)	Irritant (XI)
R-phrases	R41
S-phrases	S26 S39
Flash point	150 °C (302 °F; 423 K)
Autoignition temperature	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).
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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

• Ethylene
• Propylene carbonate

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. Hans-Josef Buysch (2005), "Carbonic Esters", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a05_197
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. doi:10.1021/j150559a041.
5. 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.