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A kinetic model for the enzyme-catalyzed self-epoxidation of oleic acid

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Journal of the American Oil Chemists' Society

Abstract

This paper reports a kinetic model for the selfepoxidation of oleic acid with toluene as solvent and Novozym 435 (a commercially available preparation of immobilized Candida antarctica lipase) as catalyst at 30°C. The effects of various parameters on the conversion and rates of reaction were studied. Both the initial rate and the progress curve data were used to fit an ordered bi-bi model. At low temperatures, the rate of epoxidation was faster than the rate of deactivation of the enzyme by hydrogen peroxide.

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References

  1. Rangarajan, B., A. Havey, E.A. Grulke, and P.D. Culnan, Kinetic Parameters of a Two-Phase Model for in situ Epoxidation of Soybean Oil, J. Am. Oil Chem. Soc. 72:1161–1169 (1995).

    CAS  Google Scholar 

  2. Kuo, M.C., and T.C. Chou, Epoxidation of Oleic Acid with Oxygen in the Presence of Benzaldehyde Using Heterogenized Homogenous Co-Type Ion-Exchange Membrane as Catalyst, Can. J. Chem. Eng. 68:831–838 (1990).

    Article  CAS  Google Scholar 

  3. Kuo, M.C., and T.C. Chou, Kinetics and Mechanism of the Catalyzed Epoxidation of Oleic Acid with Oxygen in the Presence of Benzaldehyde, Ind. Eng. Chem. Res. 26:277–284 (1987).

    Article  CAS  Google Scholar 

  4. Rastogi, A., A. Vega, C. Georgakis, and H.G. Stenger, Jr., Optimization of Catalyzed Epoxidation of Unsaturated Fatty Acids by Using Tendency Models, Chem. Eng. Sci. 45:2067–2074 (1990).

    Article  CAS  Google Scholar 

  5. Chou, T.C., and S.V. Lee, Epoxidation of Oleic Acid in the Pressence of Benzaldehyde Using Cobalt (II) Tetraphenylporphyrine as Catalyst, Ind. Eng. Chem. Res. 36:1485–1490 (1997).

    Article  CAS  Google Scholar 

  6. gen Klaas, M.R., and S. Warwel, Enzymatic Preparation of Peroxy-.Epoxy-and Peroxy-Epoxy Fatty Acids, in Oils—Fats—Lipids 1995, Proceedings of the 21st World Congress of the International Society for Research (ISF), Den Haag, October, 1995, P.J. Barnes, and Ass., Bridgwater, United Kingdom, 1996, Vol. 3, pp. 469–471.

  7. Warwel, S., and M.R. gen Klass, Chemo-Enzymatic Epoxidation of Unsaturated Carboxylic Acids, J. Mol. Cat. B: Enz. 1: 29–35 (1995).

    Article  CAS  Google Scholar 

  8. Jay, R.R., Direct Titration of Epoxy Compounds and Aziridines, Anal. Chem. 36:667–668 (1964).

    Article  CAS  Google Scholar 

  9. Lucas, H.L., and D. Pressman, Determination of Unsaturation in Organic Compounds by Means of the Mercury-Catalyzed Reaction with Standard Bromate-Bromide Solution, Ind. Eng. Chem., Anal. Ed. 10:140–142 (1938).

    Article  CAS  Google Scholar 

  10. Björkling, F., H. Frykman, S.E. Godtfredsen, and O. Kirk, Lipase Catalyzed Synthesis of Peroxycarboxylic Acids and Lipase Mediated Oxidations, Tetrahedron 48:4587–4592 (1995).

    Article  Google Scholar 

  11. Björkling F., S.E. Godtfredsen, and O. Kirk, Lipase-Mediated Formation of Peroxycarboxylic Acids Used in Catalytic Epoxidation of Alkenes, J. Chem. Soc., Chem. Commun. 1301–1303 (1990).

  12. Bailey, J.E., and D.F. Ollis, Biochemical Engineering Fundaments, McGraw-Hill Publishers, New York, 1986, p. 219.

    Google Scholar 

  13. Fogler, H.S., Elements of Chemical Reaction Engineering, Prentice-Hall, New Delhi, India (1995).

    Google Scholar 

  14. Manjula Devi, K., Catalysis in Organic Synthesis, Ph.D. Thesis, University of Mumbai, Mumbai, India, 1999.

    Google Scholar 

  15. Arroyo, M., and J.V. Sinistera, High Enantioselective Esterification of 2-Aryl Propionic Acids Catalyzed by Immobilized Lipase from Candida antarctica: A Mechanistic Approach, J. Org. Chem. 59:4410–4418 (1994).

    Article  CAS  Google Scholar 

  16. Uppenberg, J., N. Öhrner, M. Norin, K. Hult, G.J. Kleywegt, S. Patkar, V. Waagen, T. Anthonsen, and A. Jones, Crystallographic and Molecular-Modeling Studies of Lipase B from Candida antarctica Reveal a Stereospecific Pocket for Secondary Alcohols, Biochemistry 34:16838–16851 (1995).

    Article  CAS  Google Scholar 

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Correspondence to G. D. Yadav.

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Yadav, G.D., Manjula Devi, K. A kinetic model for the enzyme-catalyzed self-epoxidation of oleic acid. J Amer Oil Chem Soc 78, 347–351 (2001). https://doi.org/10.1007/s11746-001-0267-2

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  • DOI: https://doi.org/10.1007/s11746-001-0267-2

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