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]

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.

1,3-Butadiene undergoes a Diels-Alder cycloaddition reaction to form 4-vinylcyclohexane.

In North America this is produced by Nippon Chemical Texas Inc. in Pasadena, TX.

Safety

4-Vinylcyclohexene is classified as a Group 2B carcinogen by the IARC ("possibly carcinogenic to humans").[3]

References

  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. ^ "Safety (MSDS) data for 4-vinylcyclohexene". Oxford University. Archived from the original on 2010-12-31. Retrieved 2009-04-19.
  3. ^ a b "4-Vinylcyclohexene" (PDF). IARC. Retrieved 2009-04-19.
  4. ^ a b 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 978-3-527-30673-2.
  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.

6. https://nctius.com/op-coproduct-streams/

Allikas: Https://en.wikipedia.org/wiki/Vinylcyclohexene
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