4-Vinylcyclohexene

4-Vinylcyclohexene

4-Vinylcyclohexene

Chemical compound

4-Vinylcyclohexene is an organic compound consisting of a vinyl group attached to the 4-position of the cyclohexene ring. It is a colorless liquid. Although chiral, it is used mainly as the racemate. It is a precursor to vinylcyclohexene dioxide.[4]

Quick Facts Names, Identifiers ...

Production

It is produced by buta-1,3-diene dimerization in a Diels-Alder reaction.[5][4] The reaction is conducted at 110 - 425 °C at pressures of 1.3 - 100 MPa in the presence of a catalyst. A mixture of silicon carbide and salts of copper or chromium comprises the catalyst. A competing product is 1,5-cyclooctadiene.

Safety

4-Vinylcyclohexene is classified as a Group 2B carcinogen by the IARC ("possibly carcinogenic to humans").[2]

References

  1. [1]
    Lide, David R. (1998). Handbook of Chemistry and Physics (87 ed.). Boca Raton, Florida: CRC Press. pp. 8–111. ISBN 0-8493-0594-2.
  2. [2]
    "4-Vinylcyclohexene" (PDF). IARC. Retrieved 2009-04-19.
  3. [3]
    "Safety (MSDS) data for 4-vinylcyclohexene". Oxford University. Archived from the original on 2010-12-31. Retrieved 2009-04-19.
  4. [4]
    Schiffer, Thomas; Oenbrink, Georg. "Cyclododecatriene, Cyclooctadiene, and 4-Vinylcyclohexene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_205.pub2. ISBN 978-3527306732.
  5. [5]
    Wittcoff, Harold; Reuben, B. G.; Plotkin, Jeffrey S. (1998). Industrial Organic Chemicals (2 ed.). Wiley-Interscience. pp. 236–7. ISBN 978-0-471-44385-8. Retrieved 2009-04-19.
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