Skip to main content
Log in

Catalytic application of mesoporous molecular sieves to vapor‐phase Beckmann rearrangement of cyclohexanone oxime

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

The vapor‐phase Beckmann rearrangement of cyclohexanone oxime to ɛ‐caprolactam catalyzed by mesoporous molecular sieves was studied. The proton‐form mesoporous molecular sieves, H‐MCM‐41 and H‐FSM‐16, exhibited extremely high activity, selectivity and stability for ɛ‐caprolactam formation when 1‐hexanol was used as diluent. The weak acid sites and/or surface silanol groups of mesoporous molecular sieves play an important role in the selective ɛ‐caprolactam formation.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. C.T. Kresge, M.E. Leonowicz, W.J. Roth, J.C. Vartuli and J.S Beck, Nature 359 (1992) 710.

    Article  CAS  Google Scholar 

  2. S. Inagaki, Y. Fukushima and K. Kuroda, J. Chem. Soc. Chem. Commun. (1993) 680.

  3. K. Roos, A. Liepold, W. Reschetilowski, R. Schmidt, A. Karlsson and M. Stoecker, Stud. Surf. Sci. Catal. 94 (1995) 389.

    Article  CAS  Google Scholar 

  4. A. Corma, A. Martinez, V. Martinez-Soria and J.B. Monton, J. Catal. 153 (1995) 25.

    Article  CAS  Google Scholar 

  5. A. Corma, M.S. Grande, V. Gonzalez-Alfaro and A.V. Orchilles, J. Catal. 159 (1996) 375.

    Article  CAS  Google Scholar 

  6. A. Aucejo, M.C. Burguet, A. Corma and V. Fornes, Appl. Catal. 22 (1986) 187 and references therein.

    Article  CAS  Google Scholar 

  7. T. Yashima, K. Miura and T. Komatsu, Stud. Surf. Sci. Catal. 84 (1994) 1897.

    CAS  Google Scholar 

  8. T. Curtin, J.P. McMonagle and B.K. Hodnett, Appl. Catal. A 93 (1992) 75.

    Article  CAS  Google Scholar 

  9. T. Curtin, J.P. McMonagle and B.K. Hodnett, Appl. Catal. A 93 (1992) 91.

    Article  CAS  Google Scholar 

  10. P.S. Singh, R. Bandyopadhyay, S.G. Hegde and B.S. Rao, Appl. Catal. A 136 (1996) 249.

    Article  CAS  Google Scholar 

  11. H. Sato, K. Hirose, M. Kitamura and Y. Nakamura, Stud. Surf. Sci. Catal. 49 (1989) 1213.

    Google Scholar 

  12. T. Ushikubo and K. Wada, J. Catal. 148 (1994) 138.

    Article  CAS  Google Scholar 

  13. S. Sato, S. Hasebe, H. Sakurai, K. Urabe and Y. Izumi, Appl. Catal. 29 (1987) 107.

    Article  CAS  Google Scholar 

  14. L.-X. Dai, R. Hayasaka, Y. Iwaki, K.A. Koyano and T. Tatsumi, J. Chem. Soc. Chem. Commun. (1996) 1071.

  15. J.S. Beck, J.C. Vartuli, W.J. Roth, M.E. Leonowicz, C.T. Kresge, K.D. Schmitt, C.T.-W. Chu, D.H. Olson, E.W. Sheppard, S.B. McCullen, J.B. Higgins and J.L. Schlenker, J. Am. Chem. Soc. 114 (1992) 10834.

    Article  CAS  Google Scholar 

  16. A. Corma, V. Fornes, M.T. Navarro and J. Perez-Pariente, J. Catal. 148 (1994) 569.

    Article  CAS  Google Scholar 

  17. C.-Y. Chen, H.-X. Li and M.E. Davis, Micropor. Mater. 2 (1993) 17.

    Article  Google Scholar 

  18. T. Tatsumi, K.A. Koyano, Y. Tanaka and S. Nakata, Chem. Lett. (1997) 469.

  19. T. Ishikawa, M. Matsuda, A. Yasukawa, K. Kandori, S. Inagaki, T. Fukushima and S. Kondo, J. Chem. Soc. Faraday Trans. 92 (1996) 1985.

    Article  CAS  Google Scholar 

  20. T. Tatsumi, K.A. Koyano, Y. Tanaka and S. Nakata, J. Porous Mater., in press.

  21. T.R. Forester and R.F. Howe, J. Am. Chem. Soc. 109 (1987) 5076.

    Article  CAS  Google Scholar 

  22. P. Salvador and W. Kladnig, J. Chem. Soc. Faraday Trans. I 73 (1977) 1153.

    Article  CAS  Google Scholar 

  23. K. Ludmila, N. Jana and N. Kveta, J. Catal. 124 (1990) 441.

    Article  Google Scholar 

  24. X.-Z. Jiang, J. Mol. Catal. A 121 (1997) 63.

    Article  CAS  Google Scholar 

  25. P.S. Landis and P.B. Venuto, J. Catal. 6 (1966) 245.

    Article  CAS  Google Scholar 

Download references

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dai, L., Koyama, K. & Tatsumi, T. Catalytic application of mesoporous molecular sieves to vapor‐phase Beckmann rearrangement of cyclohexanone oxime. Catalysis Letters 53, 211–214 (1998). https://doi.org/10.1023/A:1019038829725

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1019038829725

Navigation