Acetic oxalic anhydride

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Acetic oxalic anhydride
Acetic oxalic anhydride.svg
Ball-and-stick model of the acetic oxalic anhydride molecule
Names
Preferred IUPAC name
Diacetic oxalic dianhydride
Other names
Diacetyl oxalate
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C6H6O6/c1-3(7)11-5(9)6(10)12-4(2)8/h1-2H3 checkY
    Key: XRMBFFGBVGXJJF-UHFFFAOYSA-N checkY
  • CC(OC(C(OC(C)=O)=O)=O)=O
Properties
C6H6O6
Molar mass 174.108 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Acetic oxalic anhydride is an organic compound with a chemical formula of C
6H
6O
6 and a structural formula of (H3C-(C=O)-O-(C=O)-)2. It can be viewed as a mixed anhydride, formally derived from acetic acid (H3C-(C=O)OH) and oxalic acid ((-(C=O)OH)2), in 2:1 molecular ratio, by the loss of two water molecules.

Preparation[]

Unlike some other anhydrides, Acetic oxalic anhydride cannot be obtained directly from the acids. It was synthesized in 1953 by and , by reacting silver oxalate (Ag
2C
2O
4) suspended in diethyl ether with acetyl chloride at temperatures below −5 °C and distilling off the solvent under low pressure. It can also be obtained by reacting anhydrous oxalic acid with ketene (H
2C=C=O).[1]

Properties[]

Acetic oxalic anhydride is an unstable colorless crystalline solid, soluble in diethyl ether, that decomposes at about −3 °C into acetic anhydride (H
3C-(C=O)-)2O, carbon dioxide (CO
2) and carbon monoxide (CO). It is hydrolyzed by water into acetic and oxalic acids.[1]

Acetic oxalic anhydride was conjectured to be an intermediate in the decomposition of anhydrous oxalic acid by acetic anhydride.[1]

See also[]

References[]

  1. ^ a b c W. R. Edwards and Walter M. Henley (1953), Acetic Oxalic Anhydride. J. Am. Chem. Soc., volume 75, issue 14, pages 3857-3859. doi:10.1021/ja01110a505
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