Dioxane tetraketone
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| Names | |||
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| IUPAC name
1,4-Dioxane-2,3,5,6-tetrone | |||
| Other names
Dimeric oxalic anhydride | |||
| Identifiers | |||
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CompTox Dashboard (EPA) |
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| Properties | |||
| C4O6 | |||
| Molar mass | 144.04 g·mol−1 | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
 verify (what is  ?) | |||
| Infobox references | |||
Dioxane tetraketone is a chemical compound with the chemical formula C4O6. It is a carbon oxide. Dioxane tetraketone is unstable as a pure compound, and breaks apart into carbon dioxide and carbon monoxide at room temperature. It is stable in solution at −30 °C.[1]
Dioxane tetraketone is an oligomer of carbon dioxide and carbon monoxide, made from two units of each compound. It decomposes into the monomers at room temperature:[2]
- C4O6 → 2 CO2 + 2 CO
It can also be thought of as a dimer of the hypothetical compound oxalic anhydride.[3]
Preparation
[change | change source]The compound is made at low temperatures by a reaction of oxalyl chloride and silver oxalate in diethyl ether:[3]
- C2O2Cl2 + Ag2C2O4 → C4O6 + 2 AgCl
Dissolving the product in deuterated chloroform and diethyl ether gave observable C4O6.[1]
References
[change | change source]- 1 2 "Molecule of the Week: Dioxane Tetraketone". American Chemical Society. 2019-09-09. Retrieved 2026-03-09.
- ↑ Gambi, A.; Giumanini, A.G.; Strazzolini, P. (2001). "Theoretical investigations on (CO)n(CO2)m cyclic cooligomers". Journal of Molecular Structure: Theochem. 536: 9–16. doi:10.1016/S0166-1280(00)00601-1.
- 1 2 Strazzolini, Paolo; Gambi, Alberto; Giumanini, Angelo G.; Vancik, Hrvoj (1998). "The reaction between ethanedioyl (Oxalyl) dihalides and Ag2C2O4: A route to Staudinger's elusive ethanedioic (Oxalic) acid anhydride". Journal of the Chemical Society, Perkin Transactions 1 (16): 2553–2558. doi:10.1039/A803430C.