Download PDF
Synlett 2010(18): 2823-2824  
DOI: 10.1055/s-0030-1258998
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Hexachloroethane

Di Wu*
College of Chemistry and Chemical Engineering, Southwest ­University, Chongqing 400715, P. R. of China
e-Mail: wulai@swu.edu.cn;
Further Information

Publication History

Publication Date:
14 October 2010 (online)

   Permissions and Reprints All articles of this category

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

  • 1a Burger JJ. Chen TBRA. De Waard ER. Huisman HO. Tetrahedron  1980,  36:  1847 
    Google Scholar
  • 1b Hommes H. Verkruijsse HD. Brandsma L. Tetrahedron Lett.  1981,  22:  2495 
    Google Scholar
  • 1c Griffen EJ. Roe DG. Snieckus V.
    J. Org. Chem.  1995,  60:  1484 
    Google Scholar
  • 1d Knoch F. Kummer S. Zenneck U. Synthesis  1996,  265 
    Google Scholar
  • 2a Wamhoff H. Berressem R. Herrmann S. Synthesis  1993,  107 
    Google Scholar
  • 2b Vorbrüggen H. Krolikiewicz K. Tetrahedron  1993,  49:  9353 
    Google Scholar
  • 3 Budavari S. The Merck Index  12th ed.; Merck & Co. Inc.; Whitehouse Station N.J.: 1996. 
    Google Scholar
  • 4 Stauffer JE. inventors; US Patent  4899000. 
  • 5 Rommel M. Ernst A. Koert U. Eur. J. Org. Chem.  2007,  26:  4408 
    Google Scholar
  • 6 Wojciechowski K. Siedlecka U. Modrzejewska H. Kosinski S. Tetrahedron  2002 58,  7583 
    CrossrefGoogle Scholar
  • 7 Shindoh N. Tokuyama H. Takemoto Y. Takasu K.
    J. Org. Chem.  2008,  73:  7451 
    CrossrefPubMedGoogle Scholar
  • 8 Cappello V. Baumgartner J. Dransfeld A. Hassler K. Eur. J. Inorg. Chem.  2006,  2006, 4589 
    Google Scholar
  • 9 Carreira M. Charernsuk M. Eberhard M. Fey N. van Ginkel R. Hamilton A. Mul WP. Orpen AG. Phetmung H. Pringle PG. J. Am. Chem. Soc.  2009,  131:  3078 
    CrossrefGoogle Scholar
  • 10 Barfoot CW. Harvey JE. Kenworthy MN. Kilburn JP. Ahmed M. Taylor RJK. Tetrahedron  2005,  61:  3403 
    CrossrefGoogle Scholar
  • 11 Saito T. Nihei H. Otani T. Suyama T. Furukawa N. Saito M. Chem. Commun.  2008,  172 
    CrossrefGoogle Scholar
  • 12 Heuser S. Keenan M. Weichert AG. Tetrahedron Lett.  2005,  46:  9001 
    CrossrefGoogle Scholar