"Ethyl carbonate" redirects here. For the monoethyl carbonate group, see Etabonate.
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 colorless liquid with a low flash point.
Diethyl carbonate is used as a solvent such as in erythromycinintramuscular 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] As a fuel additive, it can reduce emissions such as volatile organic compounds, CO2, and particulates.[7]
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.
It can also be made by the alcoholysis of urea with ethanol. This reaction requires a heterogeneous catalysis that can act both as a Lewis acid and a base, such as various metal oxides. The reaction proceeds via the formation of the intermediary ethyl carbamate.[7]
^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. PMID 14367139.
^US 4382086, Sciavolino, Frank C. & Hauske, James R., "9-Dihydro-11,12-ketal derivatives of erythromycin A and epi-erythromycin A", published 1983-05-03, issued 1982-03-01, assigned to Pfizer Inc.
^US 4363803, Hauske, James R., "3",4"-Oxyallylene erythromycin and oleandomycin, composition and method of use", published 1982-12-14, issued 1982-03-01, assigned to Pfizer Inc.
^Walter, K. Scientists Discover Method for Cleaner Fossil Fuel. MR&D Magazine. 09/18/2017 - 3:16pm
^ abcShukla, Kartikeya; Srivastava, Vimal Chandra (2016). "Diethyl carbonate: critical review of synthesis routes, catalysts used and engineering aspects". RSC Advances. 6 (39): 32624–32645. Bibcode:2016RSCAd...632624S. doi:10.1039/c6ra02518h. Retrieved Aug 3, 2021.
^Rad, Bio-. "Bio-Gel A Gels - Instruction Manual" (PDF). Retrieved 12 April 2023.
December 15, 2023
diethyl, carbonate, ethyl, carbonate, redirects, here, monoethyl, carbonate, group, etabonate, sometimes, abbreviated, ester, carbonic, acid, ethanol, with, formula, och2ch3, room, temperature, diethyl, carbonate, colorless, liquid, with, flash, point, namespr. Ethyl carbonate redirects here For the monoethyl carbonate group see Etabonate 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 colorless liquid with a low flash point Diethyl carbonate NamesPreferred IUPAC name Diethyl carbonateOther names Carbonic ether Ethyl carbonate di Eufin 1 IdentifiersCAS Number 105 58 8 Y3D model JSmol Interactive imageChEMBL ChEMBL1533495ChemSpider 7478 YECHA InfoCard 100 003 011EC Number 203 311 1PubChem CID 7766RTECS number FF9800000UNII 3UA92692HG NUN number 2366CompTox Dashboard EPA DTXSID3025041InChI InChI 1S C5H10O3 c1 3 7 5 6 8 4 2 h3 4H2 1 2H3 YKey OIFBSDVPJOWBCH UHFFFAOYSA N YSMILES O C OCC OCCPropertiesChemical formula C 5H 10O 3Molar mass 118 132 g mol 1Appearance Colorless liquidDensity 0 975 g cm3Melting point 43 C 45 F 230 K 2 Boiling point 125 9 C 258 6 F 399 0 K 2 Solubility in water InsolubleHazardsGHS labelling PictogramsSignal word WarningHazard statements H226 H315 H319 H335Precautionary 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 P501Flash 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 Y N 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 minimizing vapor buildup in warm weather that can block fuel lines 6 As a fuel additive it can reduce emissions such as volatile organic compounds CO2 and particulates 7 Contents 1 Production 2 Use in biological research 3 See also 4 ReferencesProduction editIt 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 2HClIt can also be made by the alcoholysis of urea with ethanol This reaction requires a heterogeneous catalysis that can act both as a Lewis acid and a base such as various metal oxides The reaction proceeds via the formation of the intermediary ethyl carbamate 7 2 CH3CH2OH CO NH2 2 CO3 CH2CH3 2 2 NH3It can also be synthesized directly from carbon dioxide and ethanol using various methods and via oxidative carbonylation with carbon monoxide Another method is transesterification from dimethyl carbonate Yet another method is from the reaction of ethyl nitrite and carbon monoxide where the ethyl nitrite can be made from nitric oxide and ethanol This method requires a catalyst such as palladium 7 Use in biological research edit0 01 v v DEC solutions can be used as a relatively gentle cold sterilizing reagent for laboratory chromatography resins 8 See also editEthylene carbonate DEPCReferences edit DIETHYL CARBONATE Retrieved 2010 02 01 a b William M Haynes ed 2016 CRC Handbook of Chemistry and Physics 97th ed CRC Press p 15 15 ISBN 978 1498754293 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 PMID 14367139 US 4382086 Sciavolino Frank C amp Hauske James R 9 Dihydro 11 12 ketal derivatives of erythromycin A and epi erythromycin A published 1983 05 03 issued 1982 03 01 assigned to Pfizer Inc US 4363803 Hauske James R 3 4 Oxyallylene erythromycin and oleandomycin composition and method of use published 1982 12 14 issued 1982 03 01 assigned to Pfizer Inc Walter K Scientists Discover Method for Cleaner Fossil Fuel MR amp D Magazine 09 18 2017 3 16pm a b c Shukla Kartikeya Srivastava Vimal Chandra 2016 Diethyl carbonate critical review of synthesis routes catalysts used and engineering aspects RSC Advances 6 39 32624 32645 Bibcode 2016RSCAd 632624S doi 10 1039 c6ra02518h Retrieved Aug 3 2021 Rad Bio Bio Gel A Gels Instruction Manual PDF Retrieved 12 April 2023 Retrieved from https en wikipedia org w index php title Diethyl carbonate amp oldid 1181160952, wikipedia, wiki, book, books, library,
