Hexafluorocyclobutene Explained

Hexafluorocyclobutene is the organofluorine compound with the formula (CF2)2(CF)2. A colorless gas, it is a precursor to a variety of compounds, including squaric acid.[1] Hexafluorocyclobutene is prepared in two steps from chlorotrifluoroethylene. The thermal dimerization gives 1,2-dichloro-1,2,3,3,4,4-hexafluorocyclobutane.[2] Dechlorination of the latter gives hexafluorocyclobutene:[3]

C4F6Cl2 + Zn -> C4F6 + ZnCl2

Safety

Reminiscent of perfluoroisobutene, hexafluorocyclobutene is quite toxic with an LD = 6000 mg/min/m−3 (mice).[4]

See also

References

  1. Book: 10.1002/0470864028.ch21 . The Chemistry of Cyclobutanes . Fluorinated Cyclobutanes and Their Derivatives. David M. Lemal, Xudong Chen . Zvi Rappoport . Joel F. Liebman. 2005. PATAI'S Chemistry of Functional Groups. 955–1029 . 0470864001 .
  2. 10.1039/JR9520003830. The High-Temperature Dimerisation of Chlorotrifluoroethylene. 1952. Buxton. M. W.. Ingram. D. W.. Smith. F.. Stacey. M.. Tatlow. J. C.. Journal of the Chemical Society (Resumed). 3830.
  3. 10.1039/JR9610003198. Some Isomeric Hexafluorocyclobutanes and Pentafluorocyclobutenes. 1961. Fuller. G.. Tatlow. J. C.. Journal of the Chemical Society (Resumed). 3198.
  4. Book: 10.1016/B978-008043405-6/50040-2. Highly-toxic fluorine compounds. Fluorine Chemistry at the Millennium. 2000. Timperley. Christopher M.. 499–538. 9780080434056.

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