Ultrasound assisted lipase catalyzed synthesis of poly-6-hydroxyhexanoate

Ultrasonic irradiation greatly improved the Candida antarctica lipase B mediated ring opening polymerization of E-caprolactone to poly-6-hydroxyhexanoate in the ionic liquid 1-ethyl-3-methylimidazolium tetraflouroborate. Compared to the conventional nonsonicated reaction, sonication improved the monomer conversion by 63% and afforded a polymer product of a narrower molecular weight distribution and a higher degree of crystallinity. Under sonication, the polydispersity index of the product was similar to 1.44 compared to a value of similar to 2.55 for the product of the conventional reaction. With sonication, nearly 75% of the monomer was converted to product, but the conversion was only similar to 16% for the reaction carried out conventionally. Compared to conventional operation, sonication enhanced the rate of polymer propagation by >2-fold and the turnover number of the lipase by >3-fold. (C) 2011 Elsevier B.V. All rights reserved.