Tetrachloroethylene oxide

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Tetrachloroethylene oxide
Tetrachloroethylene oxide.svg
Names
IUPAC name
tetrachlorooxirane
Other names
Perchloroethylene oxide (PCEO), Epoxyperchlorovinyl, Tetrachloroepoxyethane
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C2Cl4O/c3-1(4)2(5,6)7-1
    Key: PHEPAUSSNBXGQO-UHFFFAOYSA-N
  • ClC1(Cl)C(Cl)(Cl)O1
Properties
C2Cl4O
Molar mass 181.82 g·mol−1
Appearanceliquid
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).

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 C2Cl4O. Tetrachloroethylene oxide is fairly stable but rearranges to trichloroacetyl chloride at higher temperatures. [4]

Contents

Production

Tetrachloroethylene oxide was first synthesised by the English chemist Frederick William Kirkbride in 1940, by exposing a mixture of oxygen and chlorine in tetrachloroethylene to UV light. [5]

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]

C2Cl4O + CH3OH → CH3O(CO)CCl3 + 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. [6]

It is metabolised to trichloroacetyl chloride which is hydrolysed to trichloroacetic acid. [7]

See also

References

  1. 1 2 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. 1 2 3 4 Frankel, Donald; Johnson, Claude; Pitt, Harold (1957). "Notes - Preparation and Properties of Tetrachloroethylene Oxide". The Journal of Organic Chemistry. 22 (9). American Chemical Society (ACS): 1119–1120. doi:10.1021/jo01360a614. ISSN   0022-3263.
  3. ↑ Raat, W. K. d. (2003). 133 Tetrachloroethylene (PER). Sweden: Arbetslivsinstitutet.
  4. 1 2 3 Campbell, R. W.; Vogl, O. (1977). "A Practical Synthesis of Tetrachloroethylene Oxide". Journal of Macromolecular Science: Part A - Chemistry. 11 (3). Informa UK Limited: 515–534. doi:10.1080/00222337708061286. ISSN   0022-233X.
  5. ↑ Oxidation of Perchloroethylene, Official Gazette of the United States Patent Office. (1943)
  6. ↑ 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
  7. ↑ Testa, B., Mayer, J. M. (2003). Hydrolysis in Drug and Prodrug Metabolism. page 633
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