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Enzymatic synthesis of oleyl oleate in dense fluids

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Journal of the American Oil Chemists’ Society

Abstract

Esterification between oleic acid and oleyl alcohol, catalyzed by theMucor miehei immobilized lipase in a batch-stirred tank reactor with supercritical carbon dioxide as solvent produced higher reaction rates at supercritical conditions than in the solvent-free system. A continuous fixed-bed reactor was designed based on the results obtained from batch experiments. At 150 bar, 40°C, and with water activity 0.46% w/w, the activity of the enzyme preparation is practically unchanged when CO2 was used as solvent. The addition of small amounts of water increases the conversion rate. The higher conversion also was observed at longer residence time. Whenn-butane was used as reaction medium, a decrease in conversion was observed.

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References

  1. Nakamura, K., M.Y. Chi, Y. Yamada and T. Yano,Chem. Eng. Commun. 45:207 (1986).

    CAS  Google Scholar 

  2. Randolph, T.W., H.W. Blanch, J.M. Prausnitz and C.R. Wilke,Biotechnol. Lett. 7:325 (1985).

    Article  CAS  Google Scholar 

  3. Hammond, D.A., M. Karel and A.M. Klibanov,Appl. Biochem. Biotech. 11:393 (1985).

    CAS  Google Scholar 

  4. Randolph, T.W., D.S. Clark, H.W. Blanch and J.M. Prausnitz,Science 238:387 (1988).

    Article  Google Scholar 

  5. Randolph, T.W., D.S. Clark, H.W. Blanch and J.M. Prausnitz,AIChE J. 34:1354 (1988).

    Article  CAS  Google Scholar 

  6. Randolph, T.W., D.S. Clark, H.W. Blanch and J.M. Prausnitz,Proc. Natl. Acad. Sci. USA 85:2979 (1988).

    Article  CAS  Google Scholar 

  7. Nakamura, K., M.Y. Chi, Y. Yamada and T. Yano,3rd World Congress on Chemical Engineering, Tokyo, 1986, p. 945.

  8. Nakamura, K., T. Hashino and T. Yano,1st International Symposium on Supercritical Fluids, edited by M. Perrut, Nice, I.N.P.L.A.R. Vandoeuvre, Oct. 17–19, 1988, p. 925.

    Google Scholar 

  9. Chi, Y.M., K. Nakamura and T. Yano,Agric. Biol. Chem. 52:1541 (1988).

    CAS  Google Scholar 

  10. Pasta, P., G. Mazzola, G. Carrea and S. Riva,Biotechnol. Lett. 2:643 (1989).

    Article  Google Scholar 

  11. Erickson, J.C., P. Schyns and C.L. Cooney,AIChE J. 36:299 (1990).

    Article  CAS  Google Scholar 

  12. Marty, A., W. Chulalaksananukul, J.S. Condoret and D. Combes,High Pressure in Biotechnology, edited by C. Balny, R. Hayashi, K. Heremans and P. Masson, John Libbey Eurotext, Montrouge, 1990, p. 461.

    Google Scholar 

  13. Härröd, M., M. Lilja-Hallberg and I. Elfman,3rd International Symposium on Supercritical Fluids, edited by G. Brunner, and M. Perrut, I.N.P.L.A.R. Nancy, Oct. 17–19, Nancy, 1994, p. 149.

    Google Scholar 

  14. De Carvalho, I.B., T.C. De Sampaio and S. Barreiros, edited by G. Brunner, and M. Perrut, I.N.P.L.A.R. Nancy, Oct. 17–19, Nancy, 1994, p. 155.

    Google Scholar 

  15. Van Eijs, A.M.M., J.P.L. de Jong, H.J. Doddema and D.R. Lindeboon,1st International Symposium on Supercritical Fluids, edited by M. Perrut, Nice, I.N.P.L.A.R., Vandoeuvre, Oct. 17–19, 1988, p. 933.

    Google Scholar 

  16. Janssens, R., J.P. van der Lugt and H.M.W. Oostrom, High Pressure in Biotechnology, edited by C. Balny, R. Hayashi, K. Heremans and P. Masson, John Libbey Eurotext, Montrouge, 1988, p. 447.

    Google Scholar 

  17. Dumont, T., D. Barth and M. Perrut,Abstract Handbook, 2nd International Symposium on High Pressure Chemical Engineering, edited by G. Vetter, Erlangen, Sept. 24–26, 1990, Dechema, Frankfurt, p. 65.

    Google Scholar 

  18. Marty, A., W. Chulalaksananukul, J.S. Condoret, R.M. Willemont and G. Durand,Biotechnol. Lett. 12:11 (1990).

    Article  CAS  Google Scholar 

  19. Dumont, T., D. Barth and M. Perrut,2nd International Symposium on Supercritical Fluids, edited by M. McHugh, Boston, May 20–22, 1991, p. 150.

  20. Dumont, T., D. Barth, C. Corbier, G. Branlant and M. Perrut,Biotechnol. Bioeng. 39:329 (1992).

    Article  Google Scholar 

  21. Marty, A., W. Chulalaksananukul, R.M. Willemont and J.S. Condoret,Biotechnol. and Bioeng. 39:273 (1992).

    Article  CAS  Google Scholar 

  22. Marty, A., D. Combes and J.S. Condoret,Biocatalysis in Non-Conventional Media, edited by J. Tramper, M.H. Vermiie, H.H. Beeftink and U. von Stockav, Elsevier, Amsterdam, 1992, p. 425.

    Google Scholar 

  23. Bernard, P., D. Barth and M. Perrut,High Pressure in Biotechnology, edited by C. Balny, R. Hayashi, K. Heremans and P. Masson, John Libbey Eurotext, Montrouge, 1992, p. 451.

    Google Scholar 

  24. Bernard, P., D. Barth and R.M. Nicoud,3rd International Symposium on Supercritical Fluids, edited by G. Brunner and M. Perrut, Nancy, I.N.P.L.A.R. Nancy, Oct. 17–19, 1994, p. 137.

    Google Scholar 

  25. Knez, Ž., and M. Habulin,Biocatalysis in Non-Conventional Media, edited by J. Tramper, M.H. Vermiie, H.H. Beeftink and U. von Stockav, Elsevier, Amsterdam, 1992, p. 401.

    Google Scholar 

  26. Knez, Ž., and M. Habulin,Biocatalysis 9:115 (1994).

    CAS  Google Scholar 

  27. Knez, Ž., V. Rižner and M. Škerget,3rd International Symposium on Supercritical Fluids, edited by G. Brunner and M. Perrut, Nancy, I.N.P.L.A.R. Nancy, Oct. 17–19, 1994, p. 143.

    Google Scholar 

  28. Shen, X.M., T.W. de Loos and J. de Swan Arons,Biocatalysis in Non-Conventional Media, edited by J. Tramper, M.H. Vermiie, H.H. Beeftink and U. von Stockav, Elsevier Science Publishers, Amsterdam, 1992, p. 417.

    Google Scholar 

  29. Dumont, T., D. Barth and M. Perrut,J. Supercrit. Fluids 6:85 (1993).

    Article  CAS  Google Scholar 

  30. Perrut, M.,High Pressure in Biotechnology, edited by C. Balny, R. Hayashi, K. Heremans and P. Masson, John Libbey Eurotext, Montrouge, 1992, p. 401.

    Google Scholar 

  31. Douglas, A.M., W.H. Blanch and J.M. Prausnitz,Ind. Eng. Chem. Res. 30:939 (1991).

    Article  Google Scholar 

  32. Adschiri, T., H. Akiya, L.C. Chin, K. Arai and K. Fujimoto,J. Chem. Eng. Jpn. 25:104 (1992).

    Article  CAS  Google Scholar 

  33. Endo, Y., K. Fujimoto and K. Arai,Developments in Food Engineering, edited by T. Yano, R. Matsuno and K. Nakamura, Blackie Academic & Professional, London, 1994, p. 849.

    Google Scholar 

  34. Martins, J., T.C. Sampaio, I.B. Carvalho, M.N. da Ponte and S. Barreiros,High Pressure in Biotechnology, edited by C. Balny, R. Hayashi, K. Heremans and P. Masson, John Libbey Eurotext, Montrouge, 1992, p. 411.

    Google Scholar 

  35. Aaltonen, O., and M. Rantakyla,2nd International Symposium on Supercritical Fluids, edited by M. McHugh, Boston, May 20–22, 1991, p. 146.

  36. Moshammer, B., B. Marr, A. Biladt and F. Froschl,Developments in Food Engineering, edited by T. Yano, R. Matsuno and K. Nakamura, Blackie Academic & Professional, London, 1994, p. 852.

    Google Scholar 

  37. Aaltonen, A., and M. Rantakyla,Chemtech.: 240 (1991).

  38. Nakamura, K.,3rd International Symposium on Supercritical Fluids, edited by G. Brunner and M. Perrut, Nancy, I.N.P.L.A.R. Nancy, Oct. 17–19, 1994, p. 121.

    Google Scholar 

  39. Knez, Ž., M. Leitgeb, D. Završnik and B. Lavrič,Fat. Sci. Technol. 92:169 (1990).

    CAS  Google Scholar 

  40. Knez, Ž., M. Habulin and S. Pečnik,Proceedings of the 5th European Congress on Biotechnology, edited by C. Christiansen, J. Munk and J. Villadsen, Munksgaard International Publishers, Copenhagen, July 8–13, 1990, p. 437.

    Google Scholar 

  41. Leitgeb, M., and Ž. Knez,J. Am. Oil Chem. Soc. 67:775 (1990).

    CAS  Google Scholar 

  42. Habulin, M., and Ž. Knez,J. Memb. Sci. 61:315 (1991).

    Article  CAS  Google Scholar 

  43. Pečnik, S., and Ž. Knez,J. Am. Oil Chem. Soc. 69:261 (1992).

    Google Scholar 

  44. Krmelj, V., M. Habulin and Ž. Knez,Fat. Sci. Technol., in press (1995).

  45. Novo Nordisk, Analytical method AF 206/2-GB, Copenhagen.

  46. Knez, Ž., and R. Steiner,J. Supercrit. Fluids 5:251 (1992).

    Article  CAS  Google Scholar 

  47. Fisher, K.,Angew Chemie 48:394 (1935).

    Google Scholar 

  48. Van Eijs, A.M.M., J.M.P. Wokke and B. Ten Brink,Preconcentration and Drying of Food Materials, edited by S. Bruin, Elsevier Amsterdam, 1988, p. 135.

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Authors and Affiliations

  1. Faculty of Chemistry and Chemical Engineering, University of Maribor, Smetanova 17, SLO-62000, Maribor, Slovenia

    Ž. Knez, V. Rižner & M. Habulin

  2. Pinus, Chemical Works, SLO-62327, Rače, Slovenia

    D. Bauman

Authors
  1. Ž. Knez
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  2. V. Rižner
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  3. M. Habulin
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  4. D. Bauman
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Knez, Ž., Rižner, V., Habulin, M. et al. Enzymatic synthesis of oleyl oleate in dense fluids. J Am Oil Chem Soc 72, 1345–1349 (1995). https://doi.org/10.1007/BF02546210

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  • DOI: https://doi.org/10.1007/BF02546210

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