Oxalic anhydride

Oxalic anhydride
Names
IUPAC name
oxiranedione
Other names
oxalic anhydride
ethanedioic anhydride
Identifiers
308818-63-5
ChemSpider 13693079 Yes
Jmol-3D images Image
Properties
C2O3
Molar mass 72.0196 g mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 Yes verify (what is: Yes/?)
Infobox references

Oxalic anhydride or ethanedioic anhydride, also called oxiranedione, is a hypothetical organic compound with the formula C2O3, which can be viewed as the anhydride of oxalic acid or the two-fold ketone of ethylene oxide. It is an oxide of carbon (an oxocarbon).

The simple compound apparently has yet to be observed (as of 2009). In 1998, however, P. Strazzolini and others have claimed the synthesis of dioxane tetraketone (C4O6), which can be viewed as the cyclic dimer of oxalic anhydride.[1]

It has been conjectured to be a fleeting intermediate in the thermal decomposition of certain oxalates[2] and certain chemoluminescent reactions of oxalyl chloride.[3]

References

  1. ↑ Paolo Strazzolini, Alberto Gambi, Angelo G. Giumanini and Hrvoj Vancik (1998). "The reaction between ethanedioyl (oxalyl) dihalides and Ag2C2O4: a route to Staudinger’s elusive ethanedioic (oxalic) acid anhydride". J. Chem. Soc., Perkin Trans. 1 (16): 2553–2558. doi:10.1039/a803430c.
  2. ↑ Ahmed A. El-Sherif, Bakir J. A. Jeragh (2007), Mixed ligand complexes of Cu(II)-2-(2-pyridyl)-benzimidazole and aliphatic or aromatic dicarboxylic acids: Synthesis, characterization and biological activity. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, volume 68, issue 1, pages 877-882. doi:10.1016/j.saa.2006.12.073
  3. ↑ M. M. Rauhut, L. J. Bollyky, R. A. Clarke, M. Loy, B. G.Roberts (1965) CHEMILUMINESCENT MATERIALS. Technical Report 9 (AD0621845), Defense Technical Information Center, 78 pages.

See also