fevereiro 2015 vol. 1 num. 2 - XX Congresso Brasileiro de Engenharia Química

Artigo - Open Access.

Idioma principal




The use of Candida antarctica lipase B immobilized in hydroxyl-propyl-methyl cellulose microemulsion-based organogels as media for the catalysis of oleic acid epoxidation with Η2Ο2, has been tested. The optimization of several reaction conditions such as temperature, concentration of substrates and the enzyme content of the organogel have been examined. For this purpose an experimental design (central composite rotatable design) was applied. The results showed that the highest yields are observed for the lower temperatures, while the enzyme and oleic acid concentrations do not affect significantly the reaction yield. A yield of 84% was obtained within 48 hours of reaction, 35° C, 0.8 mg of enzyme/ml of microemulsion and 1.2 mL of H2O2. Moreover, the reusability of the catalyst has been verified.



DOI: 10.5151/chemeng-cobeq2014-0251-26330-155429

Referências bibliográficas
  • [1] Biasutti, M. A. Kinetics of reactions catalyzed by enzymes in solutions of surfactants. Adv. Col. Interf. Sc., 136, 1-24, 2008.
  • [2] Bjorkling, F., Godtfredsen, S., Andamp; Kirk, O. Lipase-mediated formation of peroxy-carboxylic acids used in catalytic epoxydation of alkenes. J. Chem. Soc., Chem. Com., 1301-1303, 1990.
  • [3] Carboni-Oerlemans, C., Dominguez de Maria, P., Tuin, B., Bargeman, G., van der Meer, A., Andamp; van Gemert, R. Hydrolase-catalysed synthesis of peroxycarboxylic acids: Biocatalytic promiscuity for practical applications. J. Biotech., 126, 140-151, 2006.
  • [4] Correa, F., Sutili, F., Miranda, L., Leite, S., De Souza, R., Andamp; Leal, I. Epoxidation of oleic acid catalyzed by PSCI-Amano lipase optimized by experimental design. J. Mol. Catal B: Enz., 81, 7-11, 2012.
  • [5] Delimitsou, C., Zoumpanioti, M., Xenakis, A., Andamp; Stamatis, A. Activity and stability studies of Mucor miehei lipase in novel microemulsion-based organogels. Biocatal. Biotransf., 20(5), 319-327, 2002.
  • [6] Warwel, S.; Klaas, M. Complete and partial epoxidation of plant oils by lipase-catalyzed perhydrolysis. Ind. Crops Prod., 9, 125-132, 1999.
  • [7] Gitin, L., Habulin, M., Knez, Z., Andamp; Hopulele, T. Some parameters optimization for enzymatic epoxidation reaction of sunflower seed oil at atmospheric pressure and 40ºC. The Annals of the University Dunarea de Jos of Galati, 2006.
  • [8] Kudanga, T., Prasetyo, E., Sipila, A., Nyanhongo, G., Andamp; Guebitz, G. Chemo-enzymatic functionalization of lignocellulose materials using oxiranes. Proc. Biochem., 45, 1557-1562, 2010.
  • [9] Lutz, J. Encyclopedia of Chemical Technology (Vol. 9). (M. Grayson, Ed.) New York: Wiley, 1980.
  • [10] Moreira, M., Bitencourt, T., Andamp; da Graca Nascimento, M. Optimization of Chemo-Enzymatic Epoxidation of Cyclohexene Mediated by Lipases. Syn. Commun., 35, 2107-2114, 2005.
  • [11] Pai, Z., Khlebnikova, T., Mattsat, Y., Andamp; Parmon, V. Catalytic oxidation of fatty acids. I. Epoxidation of unsaturated fatty acids. Reac. Kin.Catal. Let., 98, 1-8, 2009.
  • [12] Pavlidis, I. G. Lipases in water-in-ionic liquid microemulsions: structural and activity studies. J. Mol. Catal. B: Enzym., 60, 50-56, 2009.
  • [13] Piazza, G., Foglia, T., Andamp; Nuniez, A. Epoxidation of fatty acids with membrane-supported peroxygenase. Biotechnol. Lets, 22, 217-221, 2000.
  • [14] Schneider, R., Lara, L., Bitencourt, T., da Graça Nascimento, M., Andamp; dos Santos Nunes, M. Chemo-Enzymatic Epoxidation of Sunflower Oil Methyl Esters. J. Braz. Chem. Soc., 20(8), 1473-1477, 2009.
  • [15] Área temática: Processos Biotecnológicos 7Sharpless, K., Andamp; Verhoeven, T. Metal-catalyzed, highly selective oxigenations of olefins and acetylenes with tert-butyl hydroperoxide. Practical conciderations and mechanisms. Aldrichim. Acta, 4, 63-74, 1979.
  • [16] Skouridou, V., Stamatis, H., Andamp; Kolisis, F. Lipase-mediated epoxidation of α-pinene. J. Mol. Catal. B: Enzym., 21, 67-69, 2003.
  • [17] Slayden, S., Liebman, J., Andamp; Sawaky, Y. The hydroxyl, ether and peroxide groups. (S. Patai, Ed.) Chichester: Wiley, 1993.
  • [18] Stamatis, H. Xenakis, A., Kolisis, F. Bioorganic reactions in microemulsions: the case of lipase. Biotechnol. Adv., 17, 293-318, 1999.
  • [19] Vogel, A., Furniss, B., Hannaford, A., Smith, P., Andamp; Tatchell, A. In Vogel''s Textbook of practical organic chemistry (pp. 1132-1135). New York: Longmann Scientific and Technical, 1989.
  • [20] Warwel, S., Andamp; ger Klaas, M. Chemo-enzymatic epoxidation of unsaturated carboxylic acids. J. Mol. Catal. B: Enzym., 1, 29-35, 1995.
  • [21] Wiles, C., Hammond, M., Andamp; Watts, P. The development and evaluation of a continuous flow process for the lipase-mediated oxidation of alkenes. Beilstein J. Org. Chem., 27(5), 2009.
  • [22] Yadav, G., Andamp; Devi, K. (2001). A kinetic model for the enzyme-catalyzed self-epoxidation of oleic acid. JAOCS, 78(4), 347-351.
  • [23] Zoumpanioti, M., Karali, M., Xenakis, A., Andamp; Stamatis, H. Lipase biocatalytic processes in surfactant free microemulsion-like ternary systems and related organogels. Enz. Microb. Technol., 39, 531-539, 2006.
  • [24] Zoumpanioti, M., Merianou, E., Karandreas, T., Stamatis, H., Andamp; Xenakis, A. Esterification of phenolic acids catalyzed by lipases immobilized in organogels. Biotechnol. Letters, 32, 1457-1462, 2010.
  • [25] Zoumpanioti, M., Parmaklis, P., Dominguez de Maria, P., Stamatis, H., Sinisterra, J., Andamp; Xenakis, A. Esterification reactions catalyzed by lipases immobilized in organogels: effect of temperature and substrate diffusion. Biotechnol. Letters, 30, 1627-1631, 2008.
  • [26] Zoumpanioti, M., Stamatis, H., Andamp; Xenakis, A. Microemulsion-based organogels as matrices for lipase immobilization. Biotechnol. Adv., 28, 395-406, 2010.
Como citar:

ZANETTE, A. F.; ZAMPAKIDI, I.; ZOUMPANIOTI, M.; SOUZA, R. O. M. A.; XENAKIS, A.; CARDOZO FILHO, L. ; "EPOXIDATION OF OLEIC ACID CATALYZED BY CANDIDA ANTARCTIC LIPASE IMMOBILIZED IN MICROEMULSION BASED ORGANOGELS", p. 383-390 . In: Anais do XX Congresso Brasileiro de Engenharia Química - COBEQ 2014 [= Blucher Chemical Engineering Proceedings, v.1, n.2]. São Paulo: Blucher, 2015.
ISSN 2359-1757, DOI 10.5151/chemeng-cobeq2014-0251-26330-155429

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