Skip to main content
SpringerLink
Log in

Kinetics and mechanism of the catalytic epoxidation of cyclohexene with tert-butyl hydroperoxide in the presence of molybdenum–squarate complex

  • Published:
Reaction Kinetics and Catalysis Letters Aims and scope Submit manuscript

Abstract

The kinetics of the catalytic epoxidation of cyclohexene with tert-butyl hydroperoxide (TBHP) in the presence of a novel molybdenum–squarate complex was studied. Both the kinetics and mechanism of the process were found to be similar to those established with the “classical” homogeneous catalysts for epoxidation.

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

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Landau, R., Sullivan, G.A., Brown, D.: Propylene oxide by the co-product processes. Chem. Technol. 602–607 (1979)

  2. Wulff, H.P.: British Patent 1249079 (1971), US Patent 3923843 (1975) to Shell Oil

  3. Sheldon, RA.: Synthetic and mechanistic aspects of metal-catalysed epoxidation with hydroperoxides. J. Mol. Catal. 7(1), 107–126 (1980)

    Article  CAS  Google Scholar 

  4. Sumegi, L., Gedra, A., Nemes, I., Hajdu, P., Gal, D.: Epoxidation studies. II. On the mechanism and kinetics of the catalytic epoxidation of propylene by alpha-phenylethyl hydroperoxide. Oxid. Commun. 3(1), 25–40 (1983)

    CAS  Google Scholar 

  5. Trifiro, F., Forzatti, P., Preite, S., Pasquon, I.: Liquid phase epoxidation of cyclohexene by tert-butyl hydroperoxide on a Mo-based catalyst. J. Less-Common Met. 36(1–2), 319–328 (1974)

    Article  CAS  Google Scholar 

  6. Sobczak, J., Ziolkowski, J.J.: Structure and catalytic reactivity of some bis-carboxylate molybdenum(V) complexes. J. Less-Common Met. 54(1), 149–157 (1977)

    Google Scholar 

  7. Yamazaki, M., Endo, H., Tokoyama, M., Kurusv, Y.: Catalytic epoxidation of cyclohexene with t-butyl hydroperoxide in the presence of various molybdenum complexes. Bull. Chem. Soc. Jpn. 56(11), 3523–3524 (1983)

    Article  CAS  Google Scholar 

  8. Sherington, D.C., Simpson, S.: Polymer-supported Mo and V cyclohexene epoxidation catalysts: activation, activity, and stability. J. Catal. 131(1), 115–126 (1991)

    Article  Google Scholar 

  9. Kotov, St.V., Kolev, Ts.M., Georgieva, M.G.: Preparation and use of novel molybdenum-containing organic complexes as catalysts in the epoxidation of cyclohexene. J. Mol. Catal. A. Chem. 195, 83–94 (2003)

    Article  CAS  Google Scholar 

  10. Kotov, St.V., Georgieva, M.G., Kolev, Ts.M.: Preparation and use of novel molybdenum-containing organic complexes as catalysts in the epoxidation of cyclohexene. II. Synthesis and applicability of molybdenum complexes based on squaric acid, 1-phenyl-1-ethanamine and 1,3-diamino-2-propanol. J. Mol. Catal. A. Chem. 207, 5–13 (2004)

    Article  CAS  Google Scholar 

  11. Topuzova, M.G., Kotov, St.V., Kolev, Ts.M.: Epoxidation of alkenes in the presence of molybdenum-squarate complexes as catalysts. Appl. Catal. A. Gen. 281, 157–166 (2005)

    Article  CAS  Google Scholar 

  12. Jay, R.R.: Direct titration of epoxy compounds and aziridines. Annal. Chem. 36(3), 667–668 (1964)

    Article  CAS  Google Scholar 

  13. Marquardt, D.W.: An algorithm for least squares estimation of nonlinear parameters. J. Soc. Ind. Appl. Math. 11(2), 431 (1963)

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. University “Prof. Dr. As. Zlatarov”, Bourgas, Bulgaria

    Encho H. Balbolov, Stefan V. Kotov, Tsonko M. Kolev & Mariana G. Topuzova

  2. Institute of Organic Chemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria

    Encho H. Balbolov, Stefan V. Kotov, Tsonko M. Kolev & Mariana G. Topuzova

Authors
  1. Encho H. Balbolov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Stefan V. Kotov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Tsonko M. Kolev
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Mariana G. Topuzova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Stefan V. Kotov.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Balbolov, E.H., Kotov, S.V., Kolev, T.M. et al. Kinetics and mechanism of the catalytic epoxidation of cyclohexene with tert-butyl hydroperoxide in the presence of molybdenum–squarate complex. React Kinet Catal Lett 97, 51–57 (2009). https://doi.org/10.1007/s11144-009-0018-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11144-009-0018-0

Keywords

Search

Navigation