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.
Similar content being viewed by others
References
Carrea, G. and Riva, S., Angew. Chem. Int. Ed., 2000, vol. 39, p. 2226.
Chen, C.-S. and Sih, C.J., Angew. Chem. Int. Ed., 1989, vol. 28, p. 695.
Gotor-Fernandez, V., Brieva, R., and Gotor, V., J. Mol. Catal., 2006, vol. 40, p. 111.
Machado, G.D.C., Paiva, L.M.C., Pinto, G.F., and Oestreicher, E.G., Enzyme Microb. Technol., 2001, vol. 28, p. 322.
Bornschauer, U.T. and Kazlauskas, R.J., Hydrolases in Organic Synthesis: Regio- and Stereoselective Biotransformations, Weinheim: Wiley-VCH, 2006.
Ghanem, A. and Aboul-Enein, H.Y., Chirality, 2005, vol. 17, p. 1.
Matsuda, T., Watanabe, K., Harada, T., Nakamura, K., Arita, Y., Misumi, Y., Ichikawa, S., and Ikariya, T., Chem. Commun., 2004, p. 2286.
Frings, K., Koch, M., and Hartmeier, W., Enzyme Microb. Technol., 1999, vol. 25, p. 303.
Kazlauskas, R.J., Trends Biotechnol., 1994, vol. 12, p. 464.
Chen, C.-S., Fujimoto, Y., Girdaukas, G., and Sih, C.J., J. Am. Chem. Soc., 1982, vol. 104, p. 7294.
Ogino, H. and Ishikawa, H., J. Biosci. Bioeng., 2001, vol. 91, p. 109.
Colombo, G., Ottolina, G., and Carrea, G., Monatsh. Chem., 2000, vol. 131, p. 527.
Zaks, A. and Klibanov, A.M., J. Biol. Chem., 1998, vol. 26, p. 1.
Narayan, V.S. and Klibanov, A.M., Biotechnol. Bioeng., 1993, vol. 41, p. 390.
Yang, L., Dordick, J.S., and Garde, S., Biophys. J., 2004, vol. 87, p. 812.
Laane, C., Boeren, S., Vos, K., and Voeger, C., Biotechnol. Bioeng., 1987, vol. 30, p. 81.
Faber, K., Biotransformations in Organic Chemistry, Berlin: Springer, 2004.
Patel, R.N., Banerjee, A., and Szarka, L.J., J. Am. Oil Chem. Soc., 1996, vol. 73, p. 1363.
Chen, J.C. and Tsai, S.W., Biotechnol. Prog., 2000, vol. 16, p. 986.
Ujang, Z., Husain, H.W., Seng, M.C., and Rashid, A.H.A., Proc. Biochem., 2003, vol. 38, p. 1483.
Lozano, P., de Diego, T., Carrie, D., Vaultier, M., and Iborra, J.L., Chem. Commun., 2002, p. 692.
Reetz, M.T., Wiesenhofer, W., Franci, G., and Leitner, W., Adv. Synth. Catal., 2003, vol. 345, p. 1221.
Jas, G. and Kirchning, A., Chem. Eur. J., 2003, vol. 9, p. 5708.
Kirchning, A., Solodenko, W., and Mennecke, K., Chem. Eur. J., 2006, vol. 12, p. 5972.
Csajagi, Cs., Szatzker, G., Toke, E.R., Urge, L., Davas, F., and Poppe, L., Tetrahedron: Asymmetry, 2008, vol. 19, p. 237.
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.
Sadana, A. and Henley, J.P., J. Biotechnol., 1988, vol. 7, p. 95.
Dixon, M. and Webb, E.C., Enzymes, New York: Academic, 1979.
Fang, Y.W., Liu, S., Wang, S.J., and Lv, M., Biochem. Eng. J., 2009, vol. 43, p. 212.
Klibanov, A.M., Tibtech, 1997, vol. 15, p. 97.
Halling, P.J., Enzyme Microb. Technol., 1994, vol. 16, p. 178.
Wehtje, E., Kaur, J., Adlercreutz, P., Chand, S., and Mattiasson, B., Enzyme Microb. Technol., 1997, vol. 21, p. 502.
Ma, L., Persson, M., and Adlercreutz, P., Enzyme Microb. Technol., 2002, vol. 31, p. 1024.
Valivety, R.H., Halling, J.P., and Macrae, A.R., FEBS Lett., 1992, vol. 301, p. 258.
Kirilin, A., Sahin, S., Maki-Arvela, P., Warna, J., Salmi, T., and Murzin, D.Yu., Int. J. Chem. Kinet., 2010, vol. 42, p. 629.
Haario, H., ModEst User’s Guide 6.1, Helsinki: Prof-Math Oy, 2002.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Kinetika i Kataliz, 2012, Vol. 53, No. 6, pp. 716–727.
The article is published in the original.
Rights and permissions
About this article
Cite this article
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
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0023158412060092