Chemistry:Tetrachloroethylene oxide
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| Names | |
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| IUPAC name
tetrachlorooxirane
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| Other names
Perchloroethylene oxide (PCEO), Epoxyperchlorovinyl, Tetrachloroepoxyethane
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| Properties | |
| C2Cl4O | |
| Molar mass | 181.82 g·mol−1 |
| Appearance | liquid |
| Density | 1.72 g/cm3[1] |
| Melting point | –58 °C[2] |
| Boiling point | 110 °C [1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Tetrachloroethylene oxide, perchloroethylene oxide (PCEO) or tetrachlorooxirane, is the perchlorinated analogue of ethylene oxide and a proposed metabolite of tetrachloroethylene.[3] It is a halogenated epoxide with the formula C
2Cl
4O. Tetrachloroethylene oxide is fairly stable but rearranges to trichloroacetyl chloride at higher temperatures.[4]
Production
The synthesis of tetrachloroethylene oxide via the oxidation of tetrachloroethylene was described by the French chemist A. Besson in 1894. He identified the compound as the epoxide of tetrachloroethylene, noted its boiling point as 110 °C and named it "oxide of perchlorinated ethylene" (oxyde d'éthylène perchloré).[5]
Tetrachloroethylene oxide was later synthesised by the English chemist Frederick William Kirkbride in 1940, by exposing a mixture of oxygen and chlorine in tetrachloroethylene to UV light.[6]
Tetrachloroethylene oxide can be obtained by the direct oxidation of tetrachloroethylene under UV light.[4]
Reactions
Unlike most epoxides, PCEO does not polymerise.[4]
PCEO reacts with methanol, with mercury(II) chloride as the catalyst, giving methyl trichloroacetate and hydrogen chloride:[2]
- C
2Cl
4O + CH
3OH → CH
3O(CO)CCl
3 + HCl
PCEO reacts with methanolic potassium hydroxide to give potassium oxalate.[2] It is slowly decomposed by dilute acid or base solutions, giving off carbon monoxide, carbon dioxide and hydrogen chloride which was possibly from the further decomposition of the intermediate oxalyl chloride.[2]
Metabolism
Tetrachloroethylene oxide (PCEO) is a short-living metabolite of tetrachloroethylene. Unlike most epoxide metabolites, PCEO does not exhibit mutagenic or carcinogenic effects.[7]
It is metabolised to trichloroacetyl chloride which is hydrolysed to trichloroacetic acid.[8]
See also
References
- ↑ 1.0 1.1 Yaws, C. L. (2015). The Yaws Handbook of Physical Properties for Hydrocarbons and Chemicals: Physical Properties for More Than 54,000 Organic and Inorganic Chemical Compounds, Coverage for C1 to C100 Organics and Ac to Zr Inorganics.
- ↑ 2.0 2.1 2.2 2.3 Frankel, Donald; Johnson, Claude; Pitt, Harold (1957). "Notes - Preparation and Properties of Tetrachloroethylene Oxide". The Journal of Organic Chemistry (American Chemical Society (ACS)) 22 (9): 1119–1120. doi:10.1021/jo01360a614. ISSN 0022-3263.
- ↑ Raat, W. K. d. (2003). 133 Tetrachloroethylene (PER). Sweden: Arbetslivsinstitutet.
- ↑ 4.0 4.1 4.2 Campbell, R. W.; Vogl, O. (1977). "A Practical Synthesis of Tetrachloroethylene Oxide". Journal of Macromolecular Science: Part A - Chemistry (Informa UK Limited) 11 (3): 515–534. doi:10.1080/00222337708061286. ISSN 0022-233X.
- ↑ A. Besson (1894), "Sur la préparation de l’éthylène perchloré et l’action de l’oxygène ozonisé sur ce corps" in Comptes rendus de l’Académie des sciences, 118 (24), p. 1347-1350
- ↑ Oxidation of Perchloroethylene, Official Gazette of the United States Patent Office. (1943)
- ↑ Maltoni, Cesare; Selikoff, Irving J; New York Academy of Sciences, [https://archive.org/details/livinginchemical0534unse/page/n10/mode/ ALKYLATING AND ACYLATING AGENTS] Living in a chemical world: occupational and environmental significance of industrial carcinogens (1988), page 629
- ↑ Testa, B., Mayer, J. M. (2003). Hydrolysis in Drug and Prodrug Metabolism. page 633
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