Diethyl carbonate

Diethyl carbonate (sometimes abbreviated DEC) is an ester of carbonic acid and ethanol with the formula OC(OCH2CH3)2. At room temperature (25 °C) diethyl carbonate is a clear liquid with a low flash point.

"Ethyl carbonate" redirects here. For the monoethyl carbonate group, see Etabonate.
Diethyl carbonate
Names
Other names
carbonic ether; ethyl carbonate; Eufin[1]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.011
UNII
Properties
C5H10O3
Molar mass 118.132 g·mol−1
Appearance Clear colorless liquid
Density 0.975 g/cm3
Melting point −74.3[2] °C (−101.7 °F; 198.8 K)
Boiling point 126 to 128 °C (259 to 262 °F; 399 to 401 K)
Insoluble
Hazards
Flammable (F)
R-phrases (outdated) R11
S-phrases (outdated) S9 S16 S29 S33
Flash point 33 °C (91 °F; 306 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Diethyl carbonate is used as a solvent such as in erythromycin intramuscular injections.[3][4] [5]It can be used as a component of electrolytes in lithium batteries. It has been proposed as a fuel additive to support cleaner diesel fuel combustion because its high boiling point might reduce blended fuels' volatility, minimize vapor buildup in warm weather that can block fuel lines.[6]

Production

It can be made by reacting phosgene with ethanol, producing hydrogen chloride as a byproduct. Because chloroform can react with oxygen to form phosgene, chloroform can be stabilized for storage by adding 1 part (by mass) of ethanol to 100 parts (by mass) of chloroform, so that any phosgene that forms is converted into diethyl carbonate.

2 CH3CH2OH + COCl2 → CO3(CH2CH3)2 + 2HCl

See also

References
  1. "DIETHYL CARBONATE". Retrieved 2010-02-01.
  2. Ding, Michael (2001). "Liquid/Solid Phase Diagrams of Binary Carbonates for Lithium Batteries". Journal of the Electrochemical Society. 148: A299–A304. doi:10.1149/1.1353568.
  3. Anderson, Robert C.; Harris, Paul N.; Chen, K. K. (1955). "Further toxicological studies with ilotycin® (Erythromycin, Lilly)". Journal of the American Pharmaceutical Association. 44 (4): 199–204. doi:10.1002/jps.3030440404. ISSN 1930-2304.
  4. , "9-Dihydro-11,12-ketal derivatives of erythromycin A and epi-erythromycin A", issued 1982-03-01
  5. , "3",4"-Oxyallylene erythromycin and oleandomycin, composition and method of use", issued 1982-03-01
  6. Walter, K. Scientists Discover Method for Cleaner Fossil Fuel. MR&D Magazine. 09/18/2017 - 3:16pm
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