| Carbon suboxide | |
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| IUPAC name | propadiene-1,3-dione |
| Identifiers | |
| CAS number | 504-64-3 |
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| Properties | |
| Molecular formula | C3O2 |
| Molar mass | 68.0309 g mol−1 |
| Appearance | colorless gas |
| Density | 0.906 ± 0.06 g/cm3, gas at 298 K |
| Melting point |
−107°C |
| Boiling point |
6.8°C |
| Structure | |
| Molecular shape | linear |
| Related compounds | |
| Related oxides | carbon dioxide carbon monoxide dicarbon monoxide carbon trioxide |
| Related compounds | carbon subnitride |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
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Carbon suboxide, or tricarbon dioxide, C3O2, has four cumulative double bonds, making it a cumulene. It is closely related to CO, CO2 and C2O, and other oxides of carbon.
Brodie discovered it in 1873 by submitting electric current to carbon monoxide.[1][2] Marcellin Berthelot created the name carbon suboxide, [3] while Otto Diels later stated that the more organic names dicarbonyl methane and dioxallene were also correct.
It is synthesized by warming a dry mixture of phosphorus pentoxide (P4O10) and malonic acid or the esters of malonic acid.[4] Therefore, it can be also considered as the anhydride of malonic anhydride, i.e. the "second anhydride" of malonic acid. Malonic anhydride (not to be confused with maleic anhydride) is a real molecule.[5]
Several other ways for synthesis and reactions of carbon suboxide can be found in a review from 1930 by Reyerson.[6]
Carbon suboxide polymerizes spontaneously to a red, yellow, or black solid. The structure is postulated to be poly(α-pyronic), similar to the structure in 2-Pyrone (α-Pyrone). [7][8] In 1969, it was proposed that the color of Martian surface is attributed to this compound, but it was shown to be a incorrect by the Viking mission.[9]
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