Skip to main content

Applications of the Olefin Metathesis Reaction to Industrial Processes

  • Chapter
Ring Opening Metathesis Polymerisation and Related Chemistry

Part of the book series: NATO Science Series ((NAII,volume 56))

Abstract

The industrial applications of the olefin metathesis reaction are relatively recent although this reaction was observed about 50 years ago. Streck described in details the historical development of this reaction in his review in a book of the same series [1]. He gave also interesting data on the industrial processes in refs. [2] and [3]. More recently, Ivin and Mol, in their classical book on olefin metathesis, have also developped this field in a special chapter [4]. The idea of olefin disproportionation was first proposed by Robert Banks at Phillips [5], who had observed traces of pentenes and propene in the reaction mixture after passing isobutane and butenes through a bed filled with molybdenum carbonyl supported on alumina. The Ring Opening Metathesis Polymerization was found by the Natta group at Montedison [6, 7]. Many groups studied this reaction and its mechanism was proposed by Chauvin

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Streck, R. (1990), in Y. Imamoglu, B. Zümreoglu-Karan and A.J. Amass (eds.), Olefin Metathesis and Polymerization Catalysts, NATO ASI Series Vol. 326, Kluwer Academic Publishers, Dordrecht, pp. 439–455.

    Book  Google Scholar 

  2. Streck, R. (1990), in Y. Imamoglu, B. Zümreoglu-Karan and A.J. Amass (eds.), Olefin Metathesis and Polymerization Catalysts, NATO ASI Series Vol. 326, Kluwer Academic Publishers, Dordrecht, pp. 457–488.

    Google Scholar 

  3. Streck, R. (1990), in Y. Imamoglu, B. Zümreoglu-Karan and A.J. Amass (eds.), Olefin Metathesis and Polymerization Catalysts, NATO ASI Series Vol. 326, Kluwer Academic Publishers, Dordrecht, pp. 489–515.

    Google Scholar 

  4. Ivin, K.J. and Mol, J.C. (1997), Olefin Metathesis and Metathesis Polymerization, Academic Press, San Diego.

    Google Scholar 

  5. Banks, R.L. (1986), ChemTech 16, 112.

    CAS  Google Scholar 

  6. Dall’Asta, G. and Mazzanti, G. (1963), Makromol. Chem. 61, 178.

    Article  Google Scholar 

  7. Dall’Asta, G. (1968), J. Polym. sci. A-1 6, 2397.

    Article  Google Scholar 

  8. Hérisson, J.L. and Chauvin, Y. (1970), Makromol. Chem. 141, 161.

    Article  Google Scholar 

  9. Peters, E.F. and Evering, B.L. (1958), U.S. pat. 2 963 471.

    Google Scholar 

  10. Banks, R.L. and Bailey, G.C. (1964), Ind. Eng. Chem., Prod. Res. Div. 3, 170.

    Article  CAS  Google Scholar 

  11. Banks, R.L. (1979), ChemTech 9, 494.

    CAS  Google Scholar 

  12. Amigues, P., Chauvin, Y., Commereuc, D., Lai, C.C., Liu, Y.H. and Pan, J.M. (1990), Hydrocarbon Process. 83, 79.

    Google Scholar 

  13. Banks, R.L., Banasiak, D.S., Hudson, P.S. and Norell, J.R. (1982) Specialty chemicals via olefin metathesis, J. Mol. Catal. 15, 21–33.

    Article  CAS  Google Scholar 

  14. Reusser, R.E. and Crain, D.L. (1974), U.S. pat. 3 729 524.

    Google Scholar 

  15. Montgomery, D.P (1972), U.S. pat. 3 707 579.

    Google Scholar 

  16. Chaumont, P. and John, C.S. (1988), J. Mol. Catal. 46, 317.

    Article  Google Scholar 

  17. Freitas, E.R. and Gum, C.R. (1979), Chem. Eng. Progr., 75.

    Google Scholar 

  18. Sherwood, M. (1982), Chem. Ind. (London), 994.

    Google Scholar 

  19. Montgomery, P.D., Moore, R.N. and Knox, W.R. (1976), U.S. pat. 3 965 206.

    Google Scholar 

  20. Innes, R.A., Sabourin, E.T. and Swift, H.E. (1979), Am. Chem. Soc., Petrol, Chem. Prepr. 24, 1065.

    CAS  Google Scholar 

  21. Innes, R.A. and Swift, H.A. (1981), ChemTech 11, 244.

    CAS  Google Scholar 

  22. Banks, R.L. (1984), in B.E. Leach (eds.), Applied Industrial Catalysis 3, Academic Press, New York, pp.215.

    Google Scholar 

  23. Logan, R.S. and Banks, R.L. (1968), Hydrocarbon Process. 61, 135.

    Google Scholar 

  24. Logan, R.S. and Banks, R.L. (1968), Oil Gas J. 66, 131.

    CAS  Google Scholar 

  25. Crain, D.L. and Reusser, R.E. (1972), Am. Chem. Soc., Petrol. Chem. Prepr. 17, E80.

    CAS  Google Scholar 

  26. Burnett, R.L. and Hughes, T.R. (1973), J. Catal. 31, 55.

    Article  CAS  Google Scholar 

  27. Chauvin, Y., Commereuc, D. and Cruypelinck, D. (1976), Makromol. Chem. 177, 2637.

    Article  CAS  Google Scholar 

  28. Graulich, W., Swodensk, W. and Theisen, D. (1972), Hydrocarbon Process., 71.

    Google Scholar 

  29. Breslow, D.S. (1990), ChemTech 20, 540.

    CAS  Google Scholar 

  30. Thorn-Csanyi, E., private communication.

    Google Scholar 

  31. Streck, R. (1982) Some applications of the olefin metathesis reaction to polymer synthesis, J. Mol. Catal. 15, 3–19.

    Article  CAS  Google Scholar 

  32. Marbach, A. and Hupp, R. (1989), Rubber World June, 30.

    Google Scholar 

  33. Mutch, A., Leconte, M., Lefebvre, F. and Basset, J.M. (1998) Effect of alcohols and epoxides on the rate of ROMP of norbornene by a ruthenium trichloride catalyst, J. Mol. Catal., A: General 133, 191–199.

    Article  CAS  Google Scholar 

  34. Bell, A; (1992), J. Mol. Catal. 76, 165.

    Article  CAS  Google Scholar 

  35. Kloziewicz, D.W. (1983), U.S. pat. 4 400 340.

    Google Scholar 

  36. Basset, J.M., Leconte, M., Ollivier, J. and Quignard, F. (1989), U.S. pat. 4 861 848.

    Google Scholar 

  37. Van Deursen, J.H. and Sjardijn, W. (1989), Chem. Mag., 669.

    Google Scholar 

  38. Kohara, T., Masayoshi, O. and Natsuume, Y. (1991), U.S. pat. 5 063 096.

    Google Scholar 

  39. Murakami, T., Kohara, T. and Tadao, N. (1992), U.S. pat. 5 106 920.

    Google Scholar 

  40. Nishi, Y., Masayoshi, O. Tadao, N. and Kohara, T. (1992), U.S. pat. 5 143 979.

    Google Scholar 

  41. Takahashi, N., Kohara, T. and Tadao, N. (1993), U.S. pat. 5 187 012

    Google Scholar 

  42. Kohara, T. and Tadao, N. (1994), U.S. pat. 5 276 098.

    Google Scholar 

  43. Kohara, T. and Tadao, N. (1994), U.S. pat. 5 302 656.

    Google Scholar 

  44. Hani, T., Nobukazu, T., Kohara, T. and Tadao, N. (1994), U.S. pat. 5 334 424.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2002 Springer Science+Business Media Dordrecht

About this chapter

Cite this chapter

Lefebvre, F. (2002). Applications of the Olefin Metathesis Reaction to Industrial Processes. In: Khosravi, E., Szymanska-Buzar, T. (eds) Ring Opening Metathesis Polymerisation and Related Chemistry. NATO Science Series, vol 56. Springer, Dordrecht. https://doi.org/10.1007/978-94-010-0373-5_21

Download citation

  • DOI: https://doi.org/10.1007/978-94-010-0373-5_21

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-1-4020-0559-6

  • Online ISBN: 978-94-010-0373-5

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics