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

It is metabolised to trichloroacetyl chloride which is hydrolysed to trichloroacetic acid. [5]

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. [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]

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]

See also

Related Research Articles

<span class="mw-page-title-main">Carboxylic acid</span> Organic compound containing a –C(=O)OH group

In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group attached to an R-group. The general formula of a carboxylic acid is often written as R−COOH or R−CO2H, sometimes as R−C(O)OH with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.

<span class="mw-page-title-main">Organic compound</span> Chemical compound with carbon-hydrogen bonds

Some chemical authorities define an organic compound as a chemical compound that contains carbon–hydrogen or carbon–carbon bonds; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-containing compounds such as alkanes and its derivatives are universally considered organic, but many others are sometimes considered inorganic, such as halides of carbon without carbon-hydrogen and carbon-carbon bonds, and certain compounds of carbon with nitrogen and oxygen.

<span class="mw-page-title-main">Potassium ferrocyanide</span> Chemical compound

Potassium ferrocyanide is the inorganic compound with formula K4[Fe(CN)6]·3H2O. It is the potassium salt of the coordination complex [Fe(CN)6]4−. This salt forms lemon-yellow monoclinic crystals.

<span class="mw-page-title-main">Potassium hydroxide</span> Inorganic compound (KOH)

Potassium hydroxide is an inorganic compound with the formula KOH, and is commonly called caustic potash.

<span class="mw-page-title-main">Tetrachloroethylene</span> Chemical compound in very wide use

Tetrachloroethylene, also known under the systematic name tetrachloroethene, or perchloroethylene, and abbreviations such as "perc" (or "PERC"), and "PCE", is a chlorocarbon with the formula Cl2C=CCl2. It is a colorless liquid widely used for dry cleaning of fabrics, hence it is sometimes called "dry-cleaning fluid". It also has its uses as an effective automotive brake cleaner. It has a mild sweet odor, detectable by most people at a concentration of 1 part per million (1 ppm).

<span class="mw-page-title-main">Manganese dioxide</span> Chemical compound

Manganese dioxide is the inorganic compound with the formula MnO
2
. This blackish or brown solid occurs naturally as the mineral pyrolusite, which is the main ore of manganese and a component of manganese nodules. The principal use for MnO
2
is for dry-cell batteries, such as the alkaline battery and the zinc–carbon battery. MnO
2
is also used as a pigment and as a precursor to other manganese compounds, such as KMnO
4
. It is used as a reagent in organic synthesis, for example, for the oxidation of allylic alcohols. MnO
2
has an α-polymorph that can incorporate a variety of atoms in the "tunnels" or "channels" between the manganese oxide octahedra. There is considerable interest in α-MnO
2
as a possible cathode for lithium-ion batteries.

<span class="mw-page-title-main">Lithium aluminium hydride</span> Chemical compound

Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula Li[AlH4] or LiAlH4. It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic synthesis, especially for the reduction of esters, carboxylic acids, and amides. The solid is dangerously reactive toward water, releasing gaseous hydrogen (H2). Some related derivatives have been discussed for hydrogen storage.

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Bisulfide is an inorganic anion with the chemical formula HS. It contributes no color to bisulfide salts, and its salts may have a distinctive putrid smell. It is a strong base. Bisulfide solutions are corrosive and attack the skin.

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<span class="mw-page-title-main">Oxalyl chloride</span> Chemical compound

Oxalyl chloride is an organic chemical compound with the formula Cl−C(=O)−C(=O)−Cl. This colorless, sharp-smelling liquid, the diacyl chloride of oxalic acid, is a useful reagent in organic synthesis.

In chemistry, disproportionation, sometimes called dismutation, is a redox reaction in which one compound of intermediate oxidation state converts to two compounds, one of higher and one of lower oxidation states. The reverse of disproportionation, such as when a compound in an intermediate oxidation state is formed from precursors of lower and higher oxidation states, is called comproportionation, also known as synproportionation.

<span class="mw-page-title-main">Phosphorous acid</span> Chemical compound (H3PO4)

Phosphorous acid is the compound described by the formula H3PO3. This acid is diprotic, not triprotic as might be suggested by this formula. Phosphorous acid is an intermediate in the preparation of other phosphorus compounds. Organic derivatives of phosphorous acid, compounds with the formula RPO3H2, are called phosphonic acids.

<span class="mw-page-title-main">Gold(III) chloride</span> Chemical compound

Gold(III) chloride, traditionally called auric chloride, is an inorganic compound of gold and chlorine with the molecular formula Au2Cl6. The "III" in the name indicates that the gold has an oxidation state of +3, typical for many gold compounds. It has two forms, the monohydrate (AuCl3·H2O) and the anhydrous form, which are both hygroscopic and light-sensitive solids. This compound is a dimer of AuCl3. This compound has a few uses, such as an oxidizing agent and for catalyzing various organic reactions.

<span class="mw-page-title-main">Sulfuryl chloride</span> Chemical compound

Sulfuryl chloride is an inorganic compound with the formula SO2Cl2. At room temperature, it is a colorless liquid with a pungent odor. Sulfuryl chloride is not found in nature, as can be inferred from its rapid hydrolysis.

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Chromium pentafluoride is the inorganic compound with the chemical formula CrF5. It is a red volatile solid that melts at 34 °C. It is the highest known chromium fluoride, since the hypothetical chromium hexafluoride has not yet been synthesized.

Silver hyponitrite is an ionic compound with formula Ag2N2O2 or (Ag+
)2[ON=NO]2−, containing monovalent silver cations and hyponitrite anions. It is a bright canary yellow solid practically insoluble in water and most organic solvents, including DMF and DMSO.

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<span class="mw-page-title-main">Europium compounds</span> Compounds with at least one europium atom

Europium compounds are compounds formed by the lanthanide metal europium (Eu). In these compounds, europium generally exhibits the +3 oxidation state, such as EuCl3, Eu(NO3)3 and Eu(CH3COO)3. Compounds with europium in the +2 oxidation state are also known. The +2 ion of europium is the most stable divalent ion of lanthanide metals in aqueous solution. Many europium compounds fluoresce under ultraviolet light due to the excitation of electrons to higher energy levels. Lipophilic europium complexes often feature acetylacetonate-like ligands, e.g., Eufod.

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. American Chemical Society (ACS). 22 (9): 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. Informa UK Limited. 11 (3): 515–534. doi:10.1080/00222337708061286. ISSN   0022-233X.
  5. Testa, B., Mayer, J. M. (2003). Hydrolysis in Drug and Prodrug Metabolism. page 633
  6. Oxidation of Perchloroethylene, Official Gazette of the United States Patent Office. (1943)