Carbon suboxide

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.

Discovery

Benjamin Brodie discovered carbon suboxide in 1873 by passing electricity through carbon monoxide. He claimed that this substance was only one of many "oxycarbons" (with formulas Cx+1Ox, i.e. C, C 2O, C3O2, C4O3, C< sub>5OR4, ...); he also said he had identified the last two oxycarbons in this series.[1][2] However, only C3O2 is known today.

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. He assumed that a carbon-rich oxide was created instead. He called this substance "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.

Characteristics

Carbon suboxide 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 carbon suboxide caused the color of Mars's surface; the Viking probes later disproved this idea.[7]

Uses

Carbon suboxide is used to make malonates and to improve the affinity of leather dyes.

References

  1. ↑ Brodie BC (1873). "Note on the Synthesis of Marsh-Gas and Formic Acid, and on the Electric Decomposition of Carbonic Oxide". Proc. R. Soc. Lond. 21 (139–147): 245–247. doi:10.1098/rspl.1872.0052. JSTOR 113037. When pure and dry carbonic oxide [=carbon monoxide] is circulated through the induction-tube, and there submitted to the action of electricity, a decomposition of the gas occurs [...] Carbonic acid [=carbon dioxide] is formed, and simultaneously with its formation a solid deposit may be observed in the induction-tube. This deposit appears as a transparent film of a red-brown color, lining the walls of the tube. It is perfectly soluble in water, which is strongly colored by it. The solution has an intensely acid reaction. The solid deposit, in the dry condition before it has been in contact with the water, is an oxide of carbon.
  2. ↑ Brodie BC (1873). "Ueber eine Synthese von Sumpfgas und Ameisensäure und die electrische Zersetzung des Kohlenoxyds". Liebigs Ann. 169 (1–2): 270–271. doi:10.1002/jlac.18731690119.
  3. ↑ Berthelot M (1891). "Action de la chaleur sur l'oxyde de carbone". Annales de Chimie et de Physique. 6 (24): 126–132. Archived from the original on 17 February 2012. Retrieved 21 Feb 2007.
  4. ↑ Reyerson LH, Kobe K (1930). "Carbon Suboxide". Chem. Rev. 7 (4): 479–492. doi:10.1021/cr60028a002.
  5. ↑ Ballauff M, Li L, Rosenfeldt S, et al. (2004). "Analysis of Poly(carbon suboxide) by Small-Angle X-ray Scattering". Angewandte Chemie International Edition. 43 (43): 5843–5846. doi:10.1002/anie.200460263. PMID 15523711.
  6. ↑ Ellern A, Drews T, Seppelt K (2001). "The Structure of Carbon Suboxide, C3O2, in the Solid State". Z. Anorg. Allg. Chem. 627 (1): 73–76. doi:10.1002/1521-3749(200101)627:1<73::AID-ZAAC73>3.0.CO;2-A.
  7. ↑ Plummer WT, Carsont RK (1969). "Mars: Is the Surface Colored by Carbon Suboxide?". Science. 166 (3909): 1141–1142. Bibcode:1969Sci...166.1141P. doi:10.1126/science.166.3909.1141. PMID 17775571. S2CID 31568906.

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