Diethyl carbonate

Diethyl carbonate
Names
	Other names carbonic ether; ethyl carbonate; Eufin
Identifiers
CAS Number	105-58-8 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1533495;
ChemSpider	7478 ;
ECHA InfoCard	100.003.011
EC Number	203-311-1;
PubChem CID	7766;
RTECS number	FF9800000;
UNII	3UA92692HG ;
UN number	2366
CompTox Dashboard (EPA)	DTXSID3025041 ;
	InChI InChI=1S/C5H10O3/c1-3-7-5(6)8-4-2/h3-4H2,1-2H3 Key: OIFBSDVPJOWBCH-UHFFFAOYSA-N ; InChI=1/C5H10O3/c1-3-7-5(6)8-4-2/h3-4H2,1-2H3 Key: OIFBSDVPJOWBCH-UHFFFAOYAX;
	SMILES O=C(OCC)OCC;
Properties
Chemical formula	C5H10O3
Molar mass	118.132 g·mol−1
Appearance	Clear colorless liquid
Density	0.975 g/cm3
Melting point	−74.3 °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 labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H315, H319, H335
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, 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). verify (what is ?) Infobox references

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 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, minimizing 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

References

^ "DIETHYL CARBONATE". Retrieved 2010-02-01.
^ 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.
^ 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.
^ [1], "9-Dihydro-11,12-ketal derivatives of erythromycin A and epi-erythromycin A", issued 1982-03-01
^ [2], "3",4"-Oxyallylene erythromycin and oleandomycin, composition and method of use", issued 1982-03-01
^ Walter, K. Scientists Discover Method for Cleaner Fossil Fuel. MR&D Magazine. 09/18/2017 - 3:16pm

[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] [1], "9-Dihydro-11,12-ketal derivatives of erythromycin A and epi-erythromycin A", issued 1982-03-01

[5] [2], "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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[6]

Production

See also

References