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Lipase-catalysed formation of macrocycles by ring-opening polymerisation of epsilon-caprolactone
KTH, School of Biotechnology (BIO), Biochemistry (closed 20130101).ORCID iD: 0000-0002-2993-9375
1998 (English)In: Polymer, ISSN 0032-3861, E-ISSN 1873-2291, Vol. 39, no 25, p. 6519-6524Article in journal (Refereed) Published
Abstract [en]

Studies were undertaken to gain mechanistic information on lactone ring-opening polymerisation reactions using Candida antarctica lipase B (Novozym 435) as the catalyst and epsilon-caprolactone as the monomer. Polymerisations were performed in organic solvents as well as without solvent at 60 degrees C. Candida antarctica lipase B catalysed concurrently with the intermolecular ring-opening polymerisation, and also the formation of macrocycles by an intramolecular condensation reaction. Candida antarctica lipase B had the highest initial rate of consumption of epsilon-caprolactone (1.2 mu mol mg(-1) min(-1)) in the bulk polymerisation, without solvent. Under these conditions, the highest average M-w, 4701 D, of poly(epsilon-caprolactone) was obtained. There were small amounts of cyclic oligomers present. When comparing the polymerisations performed in dioxane, acetonitrile and THF after 24 h reaction time with the bulk polymerisation, the average M-w of poly(epsilon-caprolactone) [2984, 1297, 1862 D, respectively] and the initial rates of monomer conversion of the enzyme (0.1, 0.05, 0.013 mu mol mg(-1) min(-1), respectively) were lower, however, the formation of cyclic oligomers was high. In dioxane, macrocycles of up to 2623 D corresponding to 23 monomer units were formed, and in acetonitrile there were mostly cyclic oligomers present. (C) 1998 Elsevier Science Ltd. All rights reserved.

Place, publisher, year, edition, pages
STFI, Swedish Pulp & Paper Res Inst, SE-11486 Stockholm, Sweden. Royal Inst Technol, Dept Biochem & Biotechnol, SE-10044 Stockholm, Sweden.: ELSEVIER SCI LTD , 1998. Vol. 39, no 25, p. 6519-6524
Keywords [en]
enzymatic ring-opening polymerisation, epsilon-caprolactone, macrocycles
National Category
Biochemistry and Molecular Biology
Identifiers
URN: urn:nbn:se:kth:diva-225144DOI: 10.1016/S0032-3861(98)00068-8ISI: 000075896900041OAI: oai:DiVA.org:kth-225144DiVA, id: diva2:1194359
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QCR 20180405

Available from: 2018-04-01 Created: 2018-04-01 Last updated: 2018-04-05Bibliographically approved

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