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Lipase-catalyzed acylation in a continuous down-flow fixed-bed reactor

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Abstract

The kinetic resolution of racemic 1-phenylethanol with ethyl acetate was investigated in a down-flow fixed-bed reactor operated in a continuous mode mainly at the molar ratio of 1: 3 in 400 mL toluene at 70°C. The catalytic activity of the immobilized lipase was studied by: (i) changing the flow rates, (ii) utilizing different substrate concentrations, (iii) applying step changes using ethyl acetate, ethyl benzene, acetic acid, acetophenone etc., (iv) investigating the inhibitory effect of either the desired or the stoichiometric products (R)-1-phenylethyl acetate and ethanol, respectively), (v) elucidating the effect of water on the activity and stability of the immobilized lipase. The residence time distribution and the reactor hydrodynamics were also discussed along with kinetic modelling. The results were linked to the one-pot reactions.

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References

  1. Carrea, G. and Riva, S., Angew. Chem. Int. Ed., 2000, vol. 39, p. 2226.

    Article  CAS  Google Scholar 

  2. Chen, C.-S. and Sih, C.J., Angew. Chem. Int. Ed., 1989, vol. 28, p. 695.

    Article  Google Scholar 

  3. Gotor-Fernandez, V., Brieva, R., and Gotor, V., J. Mol. Catal., 2006, vol. 40, p. 111.

    Article  CAS  Google Scholar 

  4. Machado, G.D.C., Paiva, L.M.C., Pinto, G.F., and Oestreicher, E.G., Enzyme Microb. Technol., 2001, vol. 28, p. 322.

    Article  CAS  Google Scholar 

  5. Bornschauer, U.T. and Kazlauskas, R.J., Hydrolases in Organic Synthesis: Regio- and Stereoselective Biotransformations, Weinheim: Wiley-VCH, 2006.

    Google Scholar 

  6. Ghanem, A. and Aboul-Enein, H.Y., Chirality, 2005, vol. 17, p. 1.

    Article  CAS  Google Scholar 

  7. Matsuda, T., Watanabe, K., Harada, T., Nakamura, K., Arita, Y., Misumi, Y., Ichikawa, S., and Ikariya, T., Chem. Commun., 2004, p. 2286.

  8. Frings, K., Koch, M., and Hartmeier, W., Enzyme Microb. Technol., 1999, vol. 25, p. 303.

    Article  CAS  Google Scholar 

  9. Kazlauskas, R.J., Trends Biotechnol., 1994, vol. 12, p. 464.

    Article  CAS  Google Scholar 

  10. Chen, C.-S., Fujimoto, Y., Girdaukas, G., and Sih, C.J., J. Am. Chem. Soc., 1982, vol. 104, p. 7294.

    Article  CAS  Google Scholar 

  11. Ogino, H. and Ishikawa, H., J. Biosci. Bioeng., 2001, vol. 91, p. 109.

    CAS  Google Scholar 

  12. Colombo, G., Ottolina, G., and Carrea, G., Monatsh. Chem., 2000, vol. 131, p. 527.

    Article  CAS  Google Scholar 

  13. Zaks, A. and Klibanov, A.M., J. Biol. Chem., 1998, vol. 26, p. 1.

    Google Scholar 

  14. Narayan, V.S. and Klibanov, A.M., Biotechnol. Bioeng., 1993, vol. 41, p. 390.

    Article  CAS  Google Scholar 

  15. Yang, L., Dordick, J.S., and Garde, S., Biophys. J., 2004, vol. 87, p. 812.

    Article  CAS  Google Scholar 

  16. Laane, C., Boeren, S., Vos, K., and Voeger, C., Biotechnol. Bioeng., 1987, vol. 30, p. 81.

    Article  CAS  Google Scholar 

  17. Faber, K., Biotransformations in Organic Chemistry, Berlin: Springer, 2004.

    Book  Google Scholar 

  18. Patel, R.N., Banerjee, A., and Szarka, L.J., J. Am. Oil Chem. Soc., 1996, vol. 73, p. 1363.

    Article  CAS  Google Scholar 

  19. Chen, J.C. and Tsai, S.W., Biotechnol. Prog., 2000, vol. 16, p. 986.

    Article  CAS  Google Scholar 

  20. Ujang, Z., Husain, H.W., Seng, M.C., and Rashid, A.H.A., Proc. Biochem., 2003, vol. 38, p. 1483.

    Article  CAS  Google Scholar 

  21. Lozano, P., de Diego, T., Carrie, D., Vaultier, M., and Iborra, J.L., Chem. Commun., 2002, p. 692.

  22. Reetz, M.T., Wiesenhofer, W., Franci, G., and Leitner, W., Adv. Synth. Catal., 2003, vol. 345, p. 1221.

    Article  CAS  Google Scholar 

  23. Jas, G. and Kirchning, A., Chem. Eur. J., 2003, vol. 9, p. 5708.

    Article  CAS  Google Scholar 

  24. Kirchning, A., Solodenko, W., and Mennecke, K., Chem. Eur. J., 2006, vol. 12, p. 5972.

    Article  Google Scholar 

  25. Csajagi, Cs., Szatzker, G., Toke, E.R., Urge, L., Davas, F., and Poppe, L., Tetrahedron: Asymmetry, 2008, vol. 19, p. 237.

    Article  CAS  Google Scholar 

  26. Maki-Arvela, P., Sahin, S., Kumar, N., Mikkola, J.-P., Eranen, K., Salmi, T., and Murzin, D.Yu., Catal. Today, 2009, vol. 140, p. 70.

    Article  Google Scholar 

  27. Sadana, A. and Henley, J.P., J. Biotechnol., 1988, vol. 7, p. 95.

    Article  CAS  Google Scholar 

  28. Dixon, M. and Webb, E.C., Enzymes, New York: Academic, 1979.

    Google Scholar 

  29. Fang, Y.W., Liu, S., Wang, S.J., and Lv, M., Biochem. Eng. J., 2009, vol. 43, p. 212.

    Article  CAS  Google Scholar 

  30. Klibanov, A.M., Tibtech, 1997, vol. 15, p. 97.

    Article  CAS  Google Scholar 

  31. Halling, P.J., Enzyme Microb. Technol., 1994, vol. 16, p. 178.

    Article  CAS  Google Scholar 

  32. Wehtje, E., Kaur, J., Adlercreutz, P., Chand, S., and Mattiasson, B., Enzyme Microb. Technol., 1997, vol. 21, p. 502.

    Article  CAS  Google Scholar 

  33. Ma, L., Persson, M., and Adlercreutz, P., Enzyme Microb. Technol., 2002, vol. 31, p. 1024.

    Article  CAS  Google Scholar 

  34. Valivety, R.H., Halling, J.P., and Macrae, A.R., FEBS Lett., 1992, vol. 301, p. 258.

    Article  CAS  Google Scholar 

  35. Kirilin, A., Sahin, S., Maki-Arvela, P., Warna, J., Salmi, T., and Murzin, D.Yu., Int. J. Chem. Kinet., 2010, vol. 42, p. 629.

    Article  CAS  Google Scholar 

  36. Haario, H., ModEst User’s Guide 6.1, Helsinki: Prof-Math Oy, 2002.

    Google Scholar 

Download references

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Correspondence to D. Yu. Murzin.

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Published in Russian in Kinetika i Kataliz, 2012, Vol. 53, No. 6, pp. 716–727.

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Sahin, S., Mäki-Arvela, P., Kangas, M. et al. Lipase-catalyzed acylation in a continuous down-flow fixed-bed reactor. Kinet Catal 53, 673–683 (2012). https://doi.org/10.1134/S0023158412060092

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  • DOI: https://doi.org/10.1134/S0023158412060092

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