Carbon suboxide
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Carbon suboxide, or tricarbon dioxide, is an oxide of carbon with the chemical formula O=C=C=C=O. Its four cumulative double bonds make it a cumulene.
The substance was discovered in 1873 by Benjamin Brodie by passing electricity through carbon monoxide. He claimed that the product was part of a series of "oxycarbons" with formulas Cx+1Ox, i.e. C, C 2O, C3O2, C4O3, C< sub>5OR4, ..., and having identified the last two;[1][2] however, only C3O2 is known.
In 1891 Marcellin Berthelot noticed that heating pure carbon monoxide to around 550°C creates small amounts of carbon dioxide but no carbon at all, and assumed that a carbon-rich oxide, was created instead. which he called "suboxide". He thought that it was the same product obtained by an electric arc and proposed the formula C2O.[3] Otto Diels later claimed that the more organic names dicarbonyl methane and dioxalene were correct as well.
It is commonly described as an oily liquid or gas at room temperature with a very noxious smell.[4]
Carbon suboxide spontaneously polymerizes to a red, yellow, or black solid. The structure is postulated to be poly(α-pyrone), similar to the structure in 2-Pyrone (α-pyrone). [5][6] In 1969, it was hypothesized that the color of the surface of Mars was caused by this compound; which was denied by the Viking probes.[7]
Uses
changeCarbon suboxide is used to make malonates; and as to improve the affinity of leather dyes.
References
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- ↑ Reyerson L. H., Kobe K. (1930). Carbon Suboxide. Vol. 7. pp. 479–492. doi:10.1021/cr60028a002.
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