Carbon suboxide
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| Carbon suboxide | |
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| IUPAC name |
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| Identifiers | |
| CAS number | [] |
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| Properties | |
| Molecular formula | C3O2 |
| Molar mass | 68.0309 g mol−1 |
| Appearance | colorless gas strong, pungent odor |
| Density | 0.906 ± 0.06 g/cm3, gas at 298 K |
| Melting point |
−111.3 °C |
| Boiling point |
6.8 °C |
| Refractive index (nD) | 1.4538 (0 °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, is an oxide of carbon with chemical formula C3O2 or O=C=C=C=O. Its four cumulative double bonds make it a cumulene. It is one of the stable members of the series of linear oxocarbons O=Cn=O, which also includes carbon dioxide (CO2) and pentacarbon dioxide (C5O2).
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.
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[edit] Synthesis
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 hypothesized that the color of Martian surface was caused by this compound; this was disproved by the Viking Mars probes.[9]
[edit] Uses
Carbon suboxide is used in the preparation of malonates; and as an auxiliary to improve the dye affinity of furs.
[edit] See also
- Carbon subsulfide, C3S2, whose structure is S=C=C=C=S
- Carbon monoxide (CO)
- Dicarbon monoxide (C2O)
- Dicarbon dioxide (C2O2)
[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. doi:. http://links.jstor.org/sici?sici=0370-1662%281872%2F1873%2921%3C245%3ANOTSOM%3E2.0.CO%3B2-J.
- ^ Brodie B. C. (1873). "Über eine Synthese von Sumpfgas und Ameisensäure und die electrische Zersetzung des Kohlenoxyds". Annalen der Chemie 169: 270. doi:.
- ^ Marcellin Berthelot (1891). "Action de la chaleur sur l'oxyde de carbone". Annales de chimie et de physique 6 (24): 126–132. http://gallica.bnf.fr/ark:/12148/bpt6k34894x/f124.table.
- ^ Diels O, Wolf B (1906). "Ueber das Kohlensuboxyd. I". Chemische Berichte 39: 689–697. doi:.
- ^ SpringerLink - Journal Article
- ^ Reyerson L. H., Kobe K. (1930). "Carbon Suboxide". Chemical Reviews 7: 479–492. doi:.
- ^ M. Ballauff, L. Li, S. Rosenfeldt, N. Dingenouts, J. Beck, P. Krieger-Beck (2004). "Analysis of Poly(carbon suboxide) by Small-Angle X-ray Scattering". Angewandte Chemie International Edition 116 (43): 5843–5846. doi:.
- ^ A. Ellern, T. Drews, K. Seppelt (2001). "The Structure of Carbon Suboxide, C3O2, in the Solid State". Zeitschrift für anorganische und allgemeine Chemie 627 (1): 73–76. doi:.
- ^ William T. Plummer & Robert K. Carsont (1969). "Mars: Is the Surface Colored by Carbon Suboxide?". Science 166: 1141. doi:.
[edit] External links
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