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Carbon suboxide
Structure of carbon suboxide
Space-filling model of carbon suboxide
IUPAC name
Identifiers
CAS number 504-64-3
PubChem 136332
ChEBI 30086
SMILES
InChI
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

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.

It is most commonly described as an evil-smelling gas.

Contents

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]

Uses

Carbon suboxide is used in the preparation of malonates; and as an auxiliary to improve the dye affinity of furs.

See also

References

  1. ^ 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:10.1098/rspl.1872.0052. http://links.jstor.org/sici?sici=0370-1662%281872%2F1873%2921%3C245%3ANOTSOM%3E2.0.CO%3B2-J.  
  2. ^ Brodie B. C. (1873). "Über eine Synthese von Sumpfgas und Ameisensäure und die electrische Zersetzung des Kohlenoxyds". Annalen der Chemie 169: 270. doi:10.1002/jlac.18731690119.  
  3. ^ 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.  
  4. ^ Diels O, Wolf B (1906). "Ueber das Kohlensuboxyd. I". Chemische Berichte 39: 689–697. doi:10.1002/cber.190603901103.  
  5. ^ SpringerLink - Journal Article
  6. ^ Reyerson L. H., Kobe K. (1930). "Carbon Suboxide". Chemical Reviews 7: 479–492. doi:10.1021/cr60028a002.  
  7. ^ 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:10.1002/anie.200460263.  
  8. ^ 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:10.1002/1521-3749(200101)627:1<73::AID-ZAAC73>3.0.CO;2-A.  
  9. ^ William T. Plummer & Robert K. Carsont (1969). "Mars: Is the Surface Colored by Carbon Suboxide?". Science 166 (3909): 1141. doi:10.1126/science.166.3909.1141. PMID 17775571.  

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