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Ethylene carbonate (sometimes abbreviated EC) 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]

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[1]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.283
Properties
C3H4O3
Molar mass 88.062 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R-phrases (outdated) R41
S-phrases (outdated) S26 S39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).
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Infobox references

Production and reactionsEdit

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 can also be produced from the reaction of urea and ethylene glycol using zinc oxide as a catalyst at a temperature of 150 °C and a pressure of 3 kPa:[4]

(NH2)2CO + HO−CH2CH2−OH → (CH2O)2CO + 2 NH3

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

ApplicationsEdit

Ethylene carbonate is used as a polar solvent with a molecular dipole moment of 4.9 D,[5][6] only 0.1 D lower than that of propylene carbonate.

It can be used as a high permittivity component of electrolytes in lithium batteries and lithium-ion batteries. Other components like diethyl carbonate, ethyl methyl carbonate, dimethyl carbonate and methyl acetate can be added to those electrolytes in order to decrease the viscosity and melting point.[7]

Ethylene carbonate is also used as plasticizer, and as a precursor to vinylene carbonate, which is used in polymers and in organic synthesis.

See alsoEdit

External linksEdit

ReferencesEdit

  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. "Carbonic Esters". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_197.
  4. ^ Bhalchandra M. Bhanage; Shin-ichiro Fujita (2003). "Transesterification of urea and ethylene glycol to ethylene carbonate as an important step for urea based dimethyl carbonate synthesis". Green Chemistry. 5 (4): 429–432. doi:10.1039/b304182d.
  5. ^ 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.
  6. ^ 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.
  7. ^ E. R. Logan; J. R. Dahn (2018). "A Study of the Physical Properties of Li-Ion Battery Electrolytes Containing Esters". J. Electrochem. Soc. 165 (2): A21–A30. doi:10.1149/2.0271802jes.