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.

Diethyl carbonate
Names
Other names
carbonic ether; ethyl carbonate; Eufin[1]
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.011
EC Number
  • 203-311-1
PubChem CID
RTECS number
  • FF9800000
UNII
UN number 2366
CompTox Dashboard (EPA)
Properties
Chemical formula
 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)
Solubility in water
 Insoluble
Hazards
GHS pictograms
GHS Signal word Warning
GHS hazard statements
 H226, H315, H319, H335
GHS precautionary statements
 P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+352, P303+361+353, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P370+378, P403+233, P403+235, P405, P501
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).
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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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