Diethyl oxalate
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Names | |
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Other names
ethyl oxalate
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Identifiers | |
3D model (JSmol)
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ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.002.241 |
EC Number |
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PubChem CID
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UNII | |
UN number | 2525 |
CompTox Dashboard (EPA)
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Properties | |
C6H10O4 | |
Molar mass | 146.142 g·mol−1 |
Appearance | colorless liquid |
Density | 1.0785 g/cm3 |
Melting point | −38.5 °C (−37.3 °F; 234.7 K) |
Boiling point | 186 °C (367 °F; 459 K) |
Hazards | |
GHS labelling:[1] | |
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Warning | |
H302, H319 | |
P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Diethyl oxalate is an organic compound with the formula (CO2CH2CH3)2. It is the diethyl ester of oxalic acid. Diethyl oxalate is a colorless liquid. It is very similar to dimethyl oxalate but is a liquid at room temperature and has lower solubility in water. Both compounds are reagents in the synthesis of more complex compounds.[1]
Production
[edit]Diethyl oxalate can be obtained by esterification of oxalic acid with ethanol using sulfuric acid as a catalyst. A procedure for the closely related dimethyl oxalate is available:[2]
- 2 CH3CH2OH + (CO2H)2 → (CO2CH2CH3)2 + 2 H2O
Reactions
[edit]Diethyl oxalate participates in many condensation reactions, usually to produce esters.[3] [4] [5]
Diethyl oxalate is often used to prepare heterocycles. It is for example a precursor to 3,4-ethylenedioxythiophene.[6] With urea, it condenses to give parabanic acid.[7]
References
[edit]- ^ Garratt, Peter J. (2001). "Diethyl Oxalate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rd207. ISBN 0-471-93623-5.
- ^ Everett Bowden (1930). "Methyl Oxalate". Organic Syntheses. 10: 78. doi:10.15227/orgsyn.010.0078.
- ^ Don E. Floyd, Sidney E. Miller (1954). "Cetylmalonic Ester". Organic Syntheses. 34: 13. doi:10.15227/orgsyn.034.0013.
- ^ P. A. Levene, G. M. Meyer (1936). "Ethyl Phenylmalonate". Organic Syntheses. 16: 33. doi:10.15227/orgsyn.016.0033.
- ^ Lester Friedman, Edward Kosower (1946). "α-Ketoglutaric Acid". Organic Syntheses. 26: 42. doi:10.15227/orgsyn.026.0042.
- ^ Pei, Qibing; Zuccarello, Guido; Ahlskog, Markus; Inganäs, Olle (1994). "Electrochromic and Highly Stable Poly(3,4-ethylenedioxythiophene) Switches Between Opaque Blue-Black and Transparent Sky Blue". Polymer. 35 (7): 1347–1351. doi:10.1016/0032-3861(94)90332-8.
- ^ Joseph I. Murray (1957). "Parabanic Acid". Organic Syntheses. 37: 71. doi:10.15227/orgsyn.037.0071.