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.
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| Other names ethyl oxalate | |
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3D model (JSmol) |
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| ECHA InfoCard | 100.002.241 |
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PubChem CID |
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| UNII |
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| 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] | |
Signal word | 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). Infobox references | |
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 CH3CH2OH + (CO2H)2 → (CO2CH2CH3)2 + 2 H2O
Reactions
Diethyl oxalate participates in many condensation reactions, usually to produce esters.
Diethyl oxalate is often used to prepare heterocycles. It is for example a precursor to 3,4-ethylenedioxythiophene. With urea, it condenses to give parabanic acid.
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