Skip to main content
SpringerLink
Log in

Kinetics of oxirane cleavage in epoxidized soybean oil

  • Technical
  • Published:
Journal of the American Oil Chemists’ Society

Abstract

The kinetics of oxirane ring cleavage in epoxidized soybean oil have been studied using glacial acetic acid at 60, 70, 80 and 90°C. It was shown that the reaction can be successfully modelled as first order with respect to the epoxide concentration and second order with respect to acetic acid. The reaction velocity constant at 70°C was found to be 2 × 10−3 1−3 hr−1 mol−2, the frequency factor, A, = 2.321 × 107 hr−1 and the energy of activation, Ea = 15.84 k cal mol−1. The effects of the concentration of acetic acid and the temperature on the net yield of epoxides by in situ epoxidation were also studied on the basis of the predicted kinetic parameters of the reaction system.

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. Rusling, J.F., G.R. Riser, M.E. Snook and W.E. Scott,J. Am. Oil Chem. Soc. 45:760 (1968).

    CAS  Google Scholar 

  2. Synthetic Organic Chemicals, U.S. Production and Sales (1963-1982), U.S. International Trade Commission, U.S. Government Printing Office, Washington, D.C.

  3. Carlson, K.D., and S.P. Chang,J. Am. Oil Chem. Soc. 62:934 (1985).

    Article  CAS  Google Scholar 

  4. Zaher, F.A., S.M. El-Shami and M.H. El-Mallah,Seifen Ole Fette Wachse 111:605 (1985).

    CAS  Google Scholar 

  5. Zaher, F.A., M.H. El-Mallah and M.M. El-Hefnawy, Fett Wissen-chaft Technologie, in press (1988).

  6. Roswsky, A., inHeterocyclic Compounds with Three and Four Membered Rings, edited by A. Weissberger, Wiley Interscience, New York, 1964, pp. 181–459.

    Google Scholar 

  7. Swern, D.,J. Am. Oil Chem. Soc. 47:424 (1970).

    Article  CAS  Google Scholar 

  8. Szakacs, S., S. Gobols and F. Nagy,J. Chem. Soc. Perkins Trans. II, 417–420 (1983).

    Article  Google Scholar 

  9. Isaacs, N.S.,Tetrahedron Lett. 4549 (1965).

  10. Isaacs, N.S., and K. Neelakantan,Can. J. Chem. 46:1043 (1968).

    Article  CAS  Google Scholar 

  11. Schmitt, W.,Z. Phys. Chem. (Frankfurt) 59:217 (1968).

    CAS  Google Scholar 

  12. Frost, A.A., and R.G. Pearson,Kinetics and Mechanism, 2nd edn, John Wiley & Sons, Inc., New York, 1961.

    Google Scholar 

  13. Chalabiev, Ch.A., M.M. Guseinov and O.A. Sadygor,C.A. 93:47545S (1980).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Fats and Oils Laboratory, National Research Centre, Dokki, Cairo, Egypt

    F. A. Zaher, M. H. El-Mallah & M. M. El-Hefnawy

Authors
  1. F. A. Zaher
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. H. El-Mallah
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. M. El-Hefnawy
    View author publications

    You can also search for this author in PubMed Google Scholar

About this article

Cite this article

Zaher, F.A., El-Mallah, M.H. & El-Hefnawy, M.M. Kinetics of oxirane cleavage in epoxidized soybean oil. J Am Oil Chem Soc 66, 698–700 (1989). https://doi.org/10.1007/BF02669955

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02669955

Keywords

Search

Navigation