Skip to main content
SpringerLink
Log in

Solvent free telomerization of butadiene with water into octadienols in the presence of nonionic surfactant: efficient micellar catalysis

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

Telomerization of butadiene with water into 2,7-octadien-1-ol using a palladiumhydrosoluble phosphine system was investigated. The reaction was carried out without solvent in the presence of carbon dioxide and a nonionic surfactant. Promoted effect of neutral surfactant appeared above the critical micelle concentration and the conversion and the selectivity depended on the structure of nonionic surfactant hydrophilic part. The role of the nonionic surfactant is discussed.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. J.R. Livingston, US Patent 5, 302, 750 (1994);

  2. C. Miyazawa, T. Mori, H. Kameo and S. Isogai, PCT Int. Appl. WO 9400, 410 (1994);

    Google Scholar 

  3. K. Koga, T. Noda and M. Oguri. JP Patent 5,155,795 (1993);

  4. A. Thome, M. Roeper and F.J. Steegmueller, DE Patent 4223363 (1993);

  5. K. Sato, I. Nakajima and Y. Misu, UK Patent 2,260,136 (1993);

  6. E. Drent, Eur. Patent Appl. 542,366 (1993);

    Google Scholar 

  7. D.L. Packett, US Patent 5,169,981 (1992).

  8. T. Yasuo, H. Tamio, H. Kenichi, M. Masami and Y. Noriaki, Eur. Patent Appl. 436, 226 (1991);

    Google Scholar 

  9. M. Roeper, W. Berteff and D. Koeffer, US Patent 4,962,243 (1990);

  10. K.E. Atkins, R.M. Manyik and G.E. O'Connor, Fr. Patent 2,045,369 (1971).

  11. R.F. Heck,Palladium Reagents in Organic Syntheses (Academic Press, London, 1985) pp. 327–337;

    Google Scholar 

  12. P.W. Jolly, R. Mynott, B. Raspel and K.P. Schick, Organometallics 5 (1986) 473, and references therein;

    Google Scholar 

  13. K. Kaneda, H. Kurosaki, M. Terasawa and S. Teranishi, J. Org. Chem. 46 (1981) 2356, and references therein.

    Google Scholar 

  14. J. Tsuji, Acc. Chem. Res. 6 (1973) 8.

    Google Scholar 

  15. E. Kuntz, Fr. Patent 2,366,237 (1976).

  16. E. Monflier, P. Bourdauducq and J.L. Couturier, PCT Int. Appl. WO 94,18147 (1994); US Patent 5,345,007 (1994);

  17. E. Monflier, P. Bourdauducq, J.L. Couturier, J. Kervennal and A. Mortreux, J. Mol. Catal. 97 (1995) 29.

    Google Scholar 

  18. E. Monflier, P. Bourdauducq, J.L. Couturier, J. Kervennal and A. Mortreux, Appl. Catal. (1995), in press.

  19. E. Monflier, P. Bourdauducq and J.L. Couturier, Fr. Patent 94,03897 (1994).

    Google Scholar 

  20. K.E. Atkins, W.E. Walker and R.M. Manvik, J. Chem. Soc. Chem. Commun. (1971) 330;

  21. U.M. Dzhemilev, V.V. Sidorova and R.V. Kunakova, Izv. Aka. Nauk SSSR, Ser. Khim. 3 (1983) 584.

    Google Scholar 

  22. J.P. Blianchini, B. Waegell, E.M. Gaydou, H. Rzehak and W. Keim, J. Mol. Catal. 10 (1981) 247.

    Google Scholar 

  23. S. Ahrland, J. Chatt, N.R. Davies and A.A. Williams, J. Chem. Soc. (1958) 276.

  24. I. Pennequin, J. Mentech, B. Thiriet, A. Mortreux and F. Petit, Fr. Patent 2,693,188 (1994);

    Google Scholar 

  25. K. Hill, B. Gruber and K.J. Weise, Tetrahedron Lett. 35 (1994) 4541.

    Google Scholar 

  26. M.J. Rosen,Surfactants and Interfacial Phenomena, 2nd Ed. (Wiley, New York, 1989).

    Google Scholar 

  27. D. Myers,Surfaces, Interfaces, and Colloids — Principles and Applications (VCH, Weinheim, 1991).

    Google Scholar 

  28. G.W. Gray and P.A. Winsor,Liquid Crystals and Plastic Crystals, Vol. 2, Physico-Chemical Properties and Methods of Investigations (Ellis Horwood, Chichester, 1974) 25.

    Google Scholar 

  29. I. Grassert, E. Paetzold and G. Oehme, Tetrahedron 30 (1993) 6605, and references therein.

    Google Scholar 

  30. P.J. Quinn and C.E. Taylor, J. Mol. Catal. 13 (1981) 389;

    Google Scholar 

  31. T.D. Madden, W.E. Peel, P.J. Quinn and D. Chapman, J. Biochem. Biophys. Meth. 2 (1980) 19.

    Google Scholar 

  32. T. Kunitake and S. Shinkai, Adv. Phys. Org. Chem. 17 (1980) 435.

    Google Scholar 

  33. D.L. Reger and M.M. Habib, J. Mol. Catal. 7 (1980) 365, and references therein;

  34. C. Lapinte and H. Riviere, Tetrahedron 43 (1977) 3817;

    Google Scholar 

  35. I. Rico, F. Couderc, E. Perez, J.P. Laval and A. Lattes, J. Chem. Soc. Chem. Commun. (1987) 1205;

  36. T.P. Murtha and T.K. Shioyama, US Patent 4,434,082 (1984);

  37. B. Fell and G. Papadogianakis, J. Mol. Catal. 66 (1991) 143;

    Google Scholar 

  38. E. Paetzold and G. Oehme, J. Prakt. Chem. 335 (1993) 181;

    Google Scholar 

  39. M.J.H. Russell and B.A. Murrer, US Patent 4,399,312 (1983);

  40. H. Bahrmann and P. Lappe, Eur. Patent Appl. 602, 463 (1994);

    Google Scholar 

  41. H. Bahrmann, G. Deckers, W. Greb, P. Heymanns, P. Lappe, T. Mueller, J. Szameitat and E. Weibus, Eur. Patent Appl. 602, 442 (1994);

    Google Scholar 

  42. H. Niels Flach, I. Grassert and G. Oehme, Macromol. Chem. Phys. 195 (1994) 3289.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Faculté des Sciences J. Perrin, Université d'Artois, Rue Jean Souvraz, Sac postal 18, 62307, Lens, France

    Eric Monflier

  2. Elf Atochem, CRRA, Rue Henri Moissan, 69310, Pierre Bénite, France

    Paul Bourdauducq, Jean-Luc Couturier & Jacques Kervennal

  3. Laboratoire de Catalyse Hétérogène et Homogène, URA CNRS 402 ENSCL, Bătiment C7, BP 108, 59652, Villeneuved'Ascq Cedex, France

    Isabelle Suisse & André Mortreux

Authors
  1. Eric Monflier
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Paul Bourdauducq
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jean-Luc Couturier
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jacques Kervennal
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Isabelle Suisse
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. André Mortreux
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Monflier, E., Bourdauducq, P., Couturier, JL. et al. Solvent free telomerization of butadiene with water into octadienols in the presence of nonionic surfactant: efficient micellar catalysis. Catal Lett 34, 201–212 (1995). https://doi.org/10.1007/BF00808335

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00808335

Keywords

Search

Navigation