Oxalic anhydride

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, 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]

Oxalic anhydride
IUPAC name
Other names
oxalic anhydride
ethanedioic anhydride
3D model (JSmol)
Molar mass 72.0196 g mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).


  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, 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

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1,4-Dioxane () is a heterocyclic organic compound, classified as an ether. It is a colorless liquid with a faint sweet odor similar to that of diethyl ether. The compound is often called simply dioxane because the other dioxane isomers (1,2- and 1,3-) are rarely encountered.

Dioxane is used as a solvent for a variety of practical applications as well as in the laboratory, and also as a stabilizer for the transport of chlorinated hydrocarbons in aluminum containers.

Acetic formic anhydride

Acetic formic anhydride is an organic compound with the chemical formula C3H4O3 and a structural formula of H3C-(C=O)-O-(C=O)H. It can be viewed as the mixed anhydride of acetic acid and formic acid.

Acetic oxalic anhydride

Acetic oxalic anhydride is an organic compound with a chemical formula of C6H6O6 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.


Acetolactone or α-acetolactone is an organic compound with formula C2H2O2. It is the smallest member of the lactone family but can also be described as the epoxide of ketene. The compound was described in 1997 as a transient species in mass spectrometry experiments.Although acetolactone itself has not been isolated in bulk, the related species bis(trifluoromethyl)acetolactone ((CF3)2C2O2), which enjoys a degree of electronic stabilisation from its two trifluoromethyl groups, is known and has a half-life of 8 h at 25 °C. This compound is prepared by photolysis of bis(trifluoromethyl)malonyl peroxide.


The molecular formula C6H6O6 (molar mass: 174.108 g/mol) may refer to:

Acetic oxalic anhydride

Aconitic acid


Dehydroascorbic acid

Compounds of carbon

Compounds of carbon are defined as chemical substances containing carbon. More compounds of carbon exist than any other chemical element except for hydrogen. Organic carbon compounds are far more numerous than inorganic carbon compounds. In general bonds of carbon with other elements are covalent bonds. Carbon is tetravalent but carbon free radicals and carbenes occur as short-lived intermediates. Ions of carbon are carbocations and carbanions are also short-lived. An important carbon property is catenation as the ability to form long carbon chains and rings.


The oxalyl cation, also known as oxalic, has the chemical formula [C2O2]2+. It is the cation derived from oxalic acid.

Chemical compounds containing the oxalyl cation include:

Oxalyl chloride, C2O2Cl2

Oxalyl fluoride, C2O2F2


An oxocarbon or oxide of carbon is a chemical compound consisting only of carbon and oxygen.The simplest and most common oxocarbons are carbon monoxide (CO) and carbon dioxide (CO2) with IUPAC names carbon(II) oxide and carbon(IV) oxide respectively. Many other stable (practically if not thermodynamically) or metastable oxides of carbon are known, but they are rarely encountered, such as carbon suboxide (C3O2 or O=C=C=C=O) and mellitic anhydride (C12O9).

While textbooks will often list only the first three, and rarely the fourth, a large number of other oxides are known today, most of them synthesized since the 1960s. Some of these new oxides are stable at room temperature. Some are metastable or stable only at very low temperatures, but decompose to simpler oxocarbons when warmed. Many are inherently unstable and can be observed only momentarily as intermediates in chemical reactions or are so reactive that they can exist only in the gas phase or under matrix isolation conditions.

The inventory of oxocarbons appears to be steadily growing. The existence of graphene oxide and of other stable polymeric carbon oxides with unbounded molecular structures suggests that many more remain to be discovered.


Polycarbonyl, (also known as polymeric-CO, p-CO or poly-CO) is a solid metastable and explosive polymer of carbon monoxide. The polymer is produced by exposing carbon monoxide to high pressures. The structure of the solid appears amorphous, but may include a zig zag of equally spaced CO groups.

Common oxides
Exotic oxides
Compounds derived from oxides


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