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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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ChemSpider | |
PubChem
CID
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UNII | |
CompTox Dashboard (
EPA)
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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).
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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]
It is metabolised to trichloroacetyl chloride which is hydrolysed to trichloroacetic acid. [5]
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. [6]
Tetrachloroethylene oxide can be obtained by the direct oxidation of tetrachloroethylene under UV light. [4]
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]
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]
![]() | |
Names | |
---|---|
IUPAC name
tetrachlorooxirane
| |
Other names
Perchloroethylene oxide (PCEO), Epoxyperchlorovinyl, Tetrachloroepoxyethane
| |
Identifiers | |
3D model (
JSmol)
|
|
ChemSpider | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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).
|
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]
It is metabolised to trichloroacetyl chloride which is hydrolysed to trichloroacetic acid. [5]
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. [6]
Tetrachloroethylene oxide can be obtained by the direct oxidation of tetrachloroethylene under UV light. [4]
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]
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]