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

Eberhard Fehling (1) , Klaus Bergander (2) , Erika Klein (1) , Nikolaus Weber (1) , Klaus Vosmann (1)

1 Max Rubner-Institute, Federal Research Institute for Nutrition and Food
2 Institute for Organic Chemistry

Copolymeric polyesters containing branched-chain methylenethiol functions, i.e., poly(1,12-dodecanedioic acid--1-thioglycerol) and poly(diethyl 1,12-dodecanedioate--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 (Novozym 435) in vacuo without drying agent in the reaction mixture. After 360-480 h, both polyesters were purified by extraction from the reaction mixtures followed by solvent fractionation. The precipitate of poly(1,12-dodecanedioic acid--1-thioglycerol) demonstrated a M of ~170,000 Da, whereas a M of ~7,100 Da only was found for poly(diethyl 1,12-dodecanedioate--1-thioglycerol). Both polycondensates were analyzed by GPC/SEC, alkali-catalyzed transmethylation, NMR- and FTIR-spectrometry.

Mots clés: Esterification; 12-Dodecanedioic acid; Immobilized lipase B from; Poly(diethyl 1; 12-dodecanedioate--1-thioglycerol); Poly(1; 12-dodecanedioic acid--1-thioglycerol); 1-Thioglycerol (3-mercaptopropane-1; 2-diol)

Eberhard Fehling, Klaus Bergander, Erika Klein, Nikolaus Weber, Klaus Vosmann. Thiol-functionalized copolymeric polyesters by lipase-catalyzed esterification and transesterification of 1,12-dodecanedioic acid and its diethyl ester, respectively, with 1-thioglycerol. Biotechnology Letters, 2010, 32 (10), pp.1463-1471. ⟨10.1007/s10529-010-0311-z⟩. ⟨hal-00594927⟩