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Towards regioselective enzymatic hydrolysis and glycerolysis of tricaprylin in miniemulsion and the direct preparation of polyurethane from the hydrolysis products

de Lima, Ana Paula D., Aschenbrenner, Eugen M., Oliveira, Sâmeque do N., Doucet, Jean-Baptiste, Weiss, Clemens K., Ziener, Ulrich, Fonseca, Luís P., Ricardo, Nágila M.P.S., de Freitas, Liane L., Petzhold, Cesar L., Landfester, Katharina
Journal of Molecular Catalysis. B, Enzymatic 2013 v.98 pp. 127-137
Burkholderia cepacia, Rhizopus arrhizus, catalytic activity, droplets, enzymatic hydrolysis, high performance liquid chromatography, hydrolysis, nuclear magnetic resonance spectroscopy, polyurethanes, solvents, temperature, triacylglycerols
Miniemulsion droplets are used as the reaction environment for the enzyme catalyzed hydrolysis and glycerolysis of tricaprylin. The reaction was conducted at slightly elevated temperatures in aqueous dispersion without any organic solvent. Lipase PS from Pseudomonas cepacia, known as a lipase without site preference (unspecific), and lipase from Rhizopus arrhizus (RAL), a lipase with sn-1,3 preference, were used for the reactions. The time courses of the conversions were studied in detail with NMR and HPLC. RAL exhibited sn-1,3 preference and Lipase PS clearly showed significant reaction in sn-2 position during hydrolysis of the triglyceride as well as during glycerolysis. From the hydrolysis products, polyurethane-based polymers were synthesized by directly adding isophoronediisocyanate to the miniemulsions after different reaction times. The properties of the products, e.g. the Tg, can be controlled by time-dependent addition of the isocyanate.