Hexachloroethane

Introduction

Hexachloroethane is a colorless, nonflammable, crystalline solid with a camphor-like odor. It is a versatile electrophilic chlorination reagent that reacts with a series of nucleophiles. [¹] Furthermore, the hexachloroethane-triphenylphoshine combination has wide applications in organic synthesis as a nucleophilic chlorination reagent. [²] Applications of hexachloroethane are quite extensive and especially industrial uses are expanding. Hexachloroethane is used in metallurgy for refining aluminium alloys and removing impurities from molten metals. Further, it is used as a degassing agent for magnesium and to inhibit the explosiveness of methane and combustion of ammonium perchlorate. It is also used as a smoke generator in grenades, in pyrotechnics, as an ignition suppressant, as a component of fire extinguishing fluids, as a polymer additive, as a flame-proofing or vulcanizing agent, and in the production of synthetic diamonds. [³]

Hexachloroethane is commercially available, but can also be easily prepared according to the procedure reported by John E. Stauffer (Scheme  [¹] ), [4] where perchloroethylene is subjected to oxychlorination with hydrogen chloride and oxygen in the presence of an oxychlorination catalyst.

Scheme 1

References

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