Carbon suboxide
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| Carbon suboxide | |
|---|---|
  |
|
| Molecular formula | C3O2 |
| Molar mass | 68.031 g mol−1 |
| Appearance | colourless gas |
| Properties | |
| Density | 3.0 kg/m³, gas at 298 K |
| Melting point | −107°C |
| Boiling point | 6.8°C |
| Molecular shape | linear |
| Related compounds | |
| Related oxides | carbon dioxide carbon monoxide dicarbon monoxide carbon trioxide |
| Related compounds | carbon subnitride |
| Infobox disclaimer and references | |
Carbon suboxide, C3O2, is a colorless pungent gas, with 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, 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. [3]
Several other ways for synthesis and reactions of carbon suboxide can be found in a review from 1930 by Reyerson.[4]
Carbon suboxide polymerizes spontaneously to a red to black solid. The structure is postulated to be poly(α-pyronic). [5] [6]
[edit] References
- ^ Brodie B. C. (1873). "Note on the Synthesis of Marsh-Gas and Formic Acid, and on the Electric Decomposition of Carbonic Oxide". Proceedings of the Royal Society (London) 21: 245-247.
- ^ Brodie B. C. (1873). "". Ann. 169: 270.
- ^ Diels O, Wolf B (1906). "". Ber. 39: 689.
- ^ Reyerson L. H., Kobe K. (1930). "Carbon Suboxide". Chemical Reviews 7: 479-492. DOI:10.1021/cr60028a002.
- ^ M. Ballauff, L. Li, S. Rosenfeldt, N. Dingenouts, J. Beck, P. Krieger-Beck. "Analysis of Poly(carbon suboxide) by Small-Angle X-ray Scattering" 116 (43): 5967 - 5970. DOI:10.1002/anie.200460263.
- ^ A. Ellern, T. Drews, K. Seppelt. "The Structure of Carbon Suboxide, C3O2, in the Solid State" 627, (1): 73 - 76. DOI:<73::AID-ZAAC73>3.0.CO;2-A 10.1002/1521-3749(200101)627:1<73::AID-ZAAC73>3.0.CO;2-A.
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