Oxalic anhydride

Names
Preferred IUPAC name

Oxiranedione

Other names

oxalic anhydride
ethanedioic anhydride

Identifiers

CAS Number

* 308818-63-5 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 13693079 Y

PubChem CID

* 23297885

CompTox Dashboard (EPA)

* DTXSID00632683

InChI

* InChI=1S/C2O3/c3-1-2(4)5-1 Y

Key: PFPYHYZFFJJQFD-UHFFFAOYSA-N Y

* InChI=1/C2O3/c3-1-2(4)5-1

Key: PFPYHYZFFJJQFD-UHFFFAOYAE

SMILES

* O=C1OC1=O

Properties

Chemical formula

| C2O3
Molar mass | 72.019 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)

Infobox references

Chemical compound

Oxalic anhydride or ethanedioic anhydride, also called oxiranedione, is a hypothetical organic compound, one of several isomers having the formula C2O3 that have been studied computationally. It 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, Paolo 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]

## See also

[edit]

* 1,2-dioxetanedione
* α-acetolactone

## References

[edit]

1. ^ Paolo Strazzolini; Alberto Gambi; Angelo G. Giumanini; 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. 68 (1): 877–882. Bibcode:2007AcSpA..68..877E. doi:10.1016/j.saa.2006.12.073. PMID 17320475.
3. ^ M. M. Rauhut; L. J. Bollyky; R. A. Clarke; M. Loy; B. G.Roberts (September 30, 1965). Chemiluminescent Materials (AD0621845) (PDF) (Technical report). Office of Naval Research and Advanced Research Projects Agency. 9. Archived (PDF) from the original on July 22, 2021.

## External links

[edit]

* Media related to Oxalic anhydride at Wikimedia Commons

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Oxocarbons

Common oxides|

* CO
* CO2

Exotic oxides|

* CO3
* CO4
* CO5
* CO6
* C2O
* C2O2
* C2O3
* C2O4 (1,2-Dioxetanedione and 1,3-Dioxetanedione)
* C3O
* C3O2
* C3O3
* C3O6
* C4O2
* C4O4
* C4O6
* C5O2
* C5O5
* C6O6 (Cyclohexanehexone and Ethylenetetracarboxylic dianhydride)
* C8O8
* C9O9
* C10O8
* C10O10
* C12O6
* C12O9
* C12O12

Polymers|

* Graphite oxide
* C3O2
* CO
* CO2

Compounds derived from oxides|

* Metal carbonyls
* Carbonic acid
* Bicarbonates
* Carbonates
* Polycarbonates (Dicarbonates and Tricarbonates)
* Peroxydicarbonates

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