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Thiol-functionalized copolymeric polyesters by lipase-catalyzed esterification and transesterification of 1,12-dodecanedioic acid and its diethyl ester, respectively, with 1-thioglycerol. | LitMetric

AI Article Synopsis

  • Researchers developed new types of copolymeric polyoxoesters using branched-chain methylenethiol functions through lipase-catalyzed polyesterification and polytransesterification processes.
  • The reaction involved 1,12-dodecanedioic acid or diethyl 1,12-dodecanedioate, and 1-thioglycerol, using an immobilized lipase B from Candida antarctica, and took between 360 to 480 hours to complete.
  • Analysis of the final products revealed that one polyoxoester had a higher molecular weight of approximately 170,000 Da compared to 7,100 Da for the other, and various analytical techniques such as GPC/SEC and NMR were used to characterize them

Article Abstract

Copolymeric polyoxoesters containing branched-chain methylenethiol functions, i.e., poly(1,12-dodecanedioic acid-co-1-thioglycerol) and poly(diethyl 1,12-dodecanedioate-co-1-thioglycerol), were formed by lipase-catalyzed polyesterification and polytransesterification of 1,12-dodecanedioic acid and diethyl 1,12-dodecanedioate, respectively, with 1-thioglycerol (3-mercaptopropane-1,2-diol) using immobilized lipase B from Candida antarctica (Novozym 435) in vacuo without drying agent in the reaction mixture. After 360-480 h, both polyoxoesters were purified by extraction from the reaction mixtures followed by solvent fractionation. The precipitate of poly(1,12-dodecanedioic acid-co-1-thioglycerol) demonstrated a M(W) of ~170,000 Da, whereas a M(W) of ~7,100 Da only was found for poly(diethyl 1,12-dodecanedioate-co-1-thioglycerol). Both polycondensates were analyzed by GPC/SEC, alkali-catalyzed transmethylation, NMR- and FTIR-spectrometry.

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Source
http://dx.doi.org/10.1007/s10529-010-0311-zDOI Listing

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