Carbon suboxide
| Names | |
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| Preferred IUPAC name
Propa-1,2-diene-1,3-dione | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| MeSH | Carbon+suboxide |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C3O2 | |
| Molar mass | 68.03 g·mol−1 |
| Appearance | colorless gas |
| Odor | strong, pungent odor |
| Density | 3.0 kg/m3, gas[1]
1.114 g/cm3, liquid[2] |
| Melting point | −111.3 °C (−168.3 °F; 161.8 K) |
| Boiling point | 6.8 °C (44.2 °F; 279.9 K) |
| reacts | |
| Solubility | soluble in 1,4-dioxane, ether, xylene, CS2, tetrahydrofuran |
Refractive index (nD)
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1.4538 (6 °C) |
| 0 D | |
| Structure | |
| rhombic | |
| quasilinear (phase dependent) | |
| Thermochemistry | |
| Std enthalpy of formation ΔfH |
−93.6 kJ/mol |
| Standard molar entropy S |
276.1 J/mol K |
| Specific heat capacity, C | 66.99 J/mol K |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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| Infobox references | |
Carbon suboxide, or tricarbon dioxide is a molecule (and therefore a chemical substance). It is an oxide of carbon (or oxocarbon). The molecule has three carbon atoms and two oxygen atoms.
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| C 3O 2 Carbon suboxide |
CO Carbon monoxide |
CO 2 Carbon dioxide |
Carbon dioxide and carbon monoxide are oxides of carbon, that are more well-known.
One way of writing the chemical formula of carbon suboxide, is O=C=C=C=O.
Uses
[change | change source]Carbon suboxide is used in the preparation of malonates; and as an auxiliary to improve the dye affinity[needs to be explained] of furs.
In chemical synthesis, carbon suboxide is a 1,3-dipole, reacting with alkenes to make 1,3‑cyclopentadiones. Because it is so unstable, it is a reagent of last resort.[3]
How to make
[change | change source]It is made by heating a dry mixture of phosphorus pentoxide (P4O10) and malonic acid or by the esters of malonic acid.[4] Therefore, carbon suboxide can also be thought of as the ketene of malonic acid. Carbon suboxide is often called "the second anhydride" of malonic acid. Malonic anhydride is a real molecule.[5]
There are several ways to make carbon suboxide and several carbon suboxide reactions.[6]
There are several ways to make carbon suboxide and several carbon suboxide reactions that can be found in a 1930 examination by Reyerson.[6]
Polymerization
[change | change source]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] The number of monomers in the polymers is variable (see Oxocarbon#Polymeric carbon oxides). In 1969, it was hypothesized that the color of the Martian surface was caused by this compound; this was disproved by the Viking Mars probes (the red color is instead due to iron oxide).[9]
More information
[change | change source]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 include carbon dioxide (CO₂) and pentacarbon dioxide (C5O2). In many ways, it is similar to carbon dioxide, and pentacarbon dioxide.
If it is carefully purified, it can exist at room temperature in the dark without decomposing. It will polymerize under certain conditions.
Benjamin Brodie found it, as he passed electricity through carbon monoxide. He said that the product was part of a series of "oxycarbons" with formulas C
x+1O_{x}, namely C
2O, C
3O
2, C
4O
3, C
5O
4,.. . He said he had identified the last two.[10][11] Only C
3O
2 is known. In 1891 Marcellin Berthelot observed that heating pure carbon monoxide to about 550 °C created small amounts of carbon dioxide but no carbon at all
. Berthelot thought that a carbon-rich oxide was created instead, which he named "sub-oxide". He assumed it was the same product obtained by electric discharge and proposed the formula C
2O.[12] Otto Diels later said that the more organic names dicarbonylmethane and dioxallene were also correct.
References
[change | change source]- ↑ "Carbon Suboxide". WebElements Periodic Table. Retrieved 19 Feb 2019.
- ↑ Weast RC, Astle MJ, eds. (1983). CRC Handbook of Chemistry and Physics (64th ed.). Boca Raton: CRC Press. p. B-82. ISBN 9780849304637.
- ↑ Kappe, Thomas (2001). "Carbon suboxide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rc015. ISBN 0-471-93623-5.
- ↑ Diels O, Wolf B (1906). Ueber das Kohlensuboxyd. Yo. Vol. 39. pp. 689–697. doi:10.1002/cber.190603901103.
{{cite book}}:|work=ignored (help) - ↑ SpringerLink - Journal Article
- ↑ 6.0 6.1 Cite error: The named reference
Reyerson_1was used but no text was provided for refs named (see the help page). - ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ Brodie BC (1873). "Note on the Synthesis of Marsh-Gas and Ant 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.
- ↑ 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.
- ↑ 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.
Other websites
[change | change source]- WebElements page on compound's properties
- "Katalog der Deutschen Nationalbibliothek" [Catalog of the German National Library]. German National Library | dnb.de (in German).