Diethyl oxalate

Last updated
Diethyl oxalate
Ethyl oxalate.svg
Names
Other names
ethyl oxalate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.241 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-464-1
PubChem CID
UNII
UN number 2525
  • InChI=1S/C6H10O4/c1-3-9-5(7)6(8)10-4-2/h3-4H2,1-2H3
    Key: WYACBZDAHNBPPB-UHFFFAOYSA-N
  • CCOC(=O)C(=O)OCC
Properties
C6H10O4
Molar mass 146.142 g·mol−1
Appearancecolorless 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:
GHS-pictogram-exclam.svg
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).

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]

Contents

Production

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

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

  1. ↑ Garratt, Peter J. (2001). "Diethyl Oxalate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rd207. ISBN   0-471-93623-5.
  2. ↑ Everett Bowden (1930). "Methyl Oxalate". Organic Syntheses. 10: 78. doi:10.15227/orgsyn.010.0078.
  3. ↑ Don E. Floyd, Sidney E. Miller (1954). "Cetylmalonic Ester". Organic Syntheses. 34: 13. doi:10.15227/orgsyn.034.0013.
  4. ↑ P. A. Levene, G. M. Meyer (1936). "Ethyl Phenylmalonate". Organic Syntheses. 16: 33. doi:10.15227/orgsyn.016.0033.
  5. ↑ Lester Friedman, Edward Kosower (1946). "α-Ketoglutaric Acid". Organic Syntheses. 26: 42. doi:10.15227/orgsyn.026.0042.
  6. ↑ 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.
  7. ↑ Joseph I. Murray (1957). "Parabanic Acid". Organic Syntheses. 37: 71. doi:10.15227/orgsyn.037.0071.
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