The chemical compound 1,3-dioxetanedione, or 1,3-dioxacyclobutane-2,4-dione is a hypothetical oxide of carbon with formula C2O4. It can be considered a cyclic dimer of carbon dioxide (CO2) or as a double ketone of 1,3-dioxetane (1,3-dioxacyclobutane).

Theoretical calculations indicate that the compound would be extremely unstable at room temperature (half-life of less than 1.1 μs); but may be stable at −196 °C.[2]

Skeletal formula of 1,3-dioxetanedione
Systematic IUPAC name
3D model (JSmol)
Molar mass 88.018 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).


  1. ^ "CID 17801328 - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 4 December 2007. Identification and Related Records. Retrieved 7 October 2011.
  2. ^ Errol Lewars (1996), Polymers and oligomers of carbon dioxide: ab initio and semiempirical calculations. Journal of Molecular Structure: THEOCHEM, Volume 363, Number 1, pp. 1–15.

The chemical compound 1,2-dioxetanedione, or 1,2-dioxacyclobutane-3,4-dione, often called peroxyacid ester, is an unstable oxide of carbon (an oxocarbon) with formula C2O4. It can be viewed as a double ketone of 1,2-dioxetane (1,2-dioxacyclobutane), or a cyclic dimer of carbon dioxide.In ordinary conditions, it quickly decomposes to carbon dioxide (CO2) even at 180 K (−93.1 °C), but can be detected by mass spectrometry and other techniques.1,2-Dioxetanedione is an intermediate in the chemoluminescent reactions used in glowsticks. The decomposition proceeds via a paramagnetic oxalate biradical intermediate.Recently it has been found that a high-energy intermediate in one of these reactions (between oxalyl chloride and hydrogen peroxide in ethyl acetate), which is presumed to be 1,2-dioxetanedione, can accumulate in solution at room temperature (up to a few micromoles at least), provided that the activating dye and all traces of metals and other reducing agents are removed from the system, and the reactions are carried out in an inert atmosphere.


C2O4 may refer to:

Compounds sharing the molecular formula:

Oxalate (ethanedioate)


1,2-Dioxetanedione (1,2-dioxetane-3,4-dione)

1,3-Dioxetanedione (1,3-dioxetane-2,4-dione)

Carbonic anhydride

Carbonic anhydride may refer to:

Carbon dioxide, the acidic oxide of carbonic acid

Dicarbonic acid, the monoanhydride of carbonic acid using two molecules

1,3-Dioxetanedione, the dianhydride of carbonic acid using two molecules

1,3,5-Trioxanetrione, the dianhydride of carbonic acid using three molecules


Dioxetanedione may refer to:




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.

Common oxides
Exotic oxides
Compounds derived from oxides


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