Tetraiodoethylene

Tetraiodoethylene

Tetraiodoethylene

Chemical compound

Tetraiodoethylene (TIE), or diiodoform, is the periodinated analogue of ethylene with the chemical formula C2I4. It is a decomposition product of carbon tetraiodide and diiodoacetylene.[5] It is an odourless yellow crystalline solid that is soluble in benzene and chloroform, and insoluble in water.[2] It has been used as an antiseptic and a component in pesticide and fungicide formulations.[6][7]

Quick Facts Names, Identifiers ...

Tetraiodoethylene reacts with ethylamine to give ethylamine di-tetraiodoethylene, EtNH2.(C2I4)2, and ethylaminetetraiodoethylene.[8] Tetraiodoethylene and iodine pentafluoride yield iodopentafluoroethane.[9]

Tetraiodoethylene turns brown and emits a "characteristic" odour due to decomposition when exposed to light.[10]

History

Tetraiodoethylene was discovered by Baeyer in 1885.[5] It was proposed as an antiseptic under the name Diiodoform, in 1893 by M. L. Maquenne and Taine.[10] It was an alternative to iodoform[10] which has a strong and persistent odour that caused difficulties for physicians in private practices.[11]

Synthesis

Tetraiodoethylene can be made by the iodination of calcium carbide:[1]

CaC2 + 3I2 → C2I4 + CaI2

Diiodoacetylene is a byproduct of the reaction which can later be iodinated to TIE.[1]

The action of aqueous solution of potassium hydroxide and iodine on barium carbide in chloroform or benzene can also give TIE.[10] Another synthesis involves mixing separate solutions of diiodoacetylene and iodine in carbon disulphide. Tetraiodoethylene would be left as a residue after carbon disulphide was evaporated.[10]

See also

References

  1. [1]
    TETRA-IODO-ETHYLENE, The Pharmaceutical Era. (1897). USA, D. O. Haynes & Company.
  2. [2]
    Lide, D. R. (1995). CRC Handbook of Chemistry and Physics. (Special Student Edition): A Ready-Reference Book of Chemical and Physical Data. CRC-Press. Page 522
  3. [3]
    Diiodoform in Notes on New Remedies. (1893). USA: Lehn & Fink.
  4. [4]
    "Tetraiodoethylene". pubchem.ncbi.nlm.nih.gov.
  5. [5]
    Peculiar Decomposition of Diiodoacetylene, Victor Meyel and Wilhelm Pemsel (1896)
  6. [6]
    The Code of Federal Regulations of the United States of America (1984). U.S. Government Printing Office.
  7. [7]
    Iodine and Plant Life: Annotated Bibliography, 1813-1949. With Review of the Literature. (1950). UK: Chilean Iodine Educational Bureau. page 22
  8. [8]
    Action of Tetraiodoethylene on Organic Bases, Chemical Abstracts. (1912). American Chemical Society.
  9. [9]
    Journal of the Chemical Society. (1948). page 2188
  10. [10]
    New Remedies – Diiodoform in Merck's Market Report and Pharmaceutical Journal: An Independent Monthly Magazine Devoted to the Professional and Commercial Interests of the Druggist. (1894).
  11. [11]
    Selections – DIIODOFORM in The International Dental Journal. (1895). USA: International Dental Publication Company.
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