Linear copolymeric poly(thia‐alkanedioates) by lipase‐catalyzed esterification and transesterification of 3,3′‐thiodipropionic acid and its dimethyl ester with α,ω‐alkanediols
Abstract Linear copolymeric polyesters (polyoxoesters) containing thioether functions [poly(3,3′‐thiodipropionic acid‐ co ‐α,ω‐alkanediols)] were formed in good yield by esterification of an equimolar mixture of 3,3′‐thiodipropionic acid (4‐thiaheptane‐1,7‐dioic acid) and 1,6‐hexanediol (weight aver...
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crwiley:10.1002/bit.21704 2024-06-02T07:58:11+00:00 Linear copolymeric poly(thia‐alkanedioates) by lipase‐catalyzed esterification and transesterification of 3,3′‐thiodipropionic acid and its dimethyl ester with α,ω‐alkanediols Fehling, E. Klein, E. Vosmann, K. Bergander, K. Weber, N. 2007 http://dx.doi.org/10.1002/bit.21704 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fbit.21704 https://onlinelibrary.wiley.com/doi/pdf/10.1002/bit.21704 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Biotechnology and Bioengineering volume 99, issue 5, page 1074-1084 ISSN 0006-3592 1097-0290 journal-article 2007 crwiley https://doi.org/10.1002/bit.21704 2024-05-03T11:19:42Z Abstract Linear copolymeric polyesters (polyoxoesters) containing thioether functions [poly(3,3′‐thiodipropionic acid‐ co ‐α,ω‐alkanediols)] were formed in good yield by esterification of an equimolar mixture of 3,3′‐thiodipropionic acid (4‐thiaheptane‐1,7‐dioic acid) and 1,6‐hexanediol (weight average molecular mass, M W >600 Da: ∼81% after 6 h) or 1,12‐dodecanediol ( M W > 900 Da: ∼90% after 6 h) catalyzed by immobilized lipase B from Candida antarctica (Novozym 435) for up to 336 h in moderate vacuo without a solvent or drying reagent in the reaction mixture. Poly (3,3′‐thiodipropionic acid‐ co ‐1,6‐hexanediol) and poly (3,3′‐thiodipropionic acid‐ co ‐1,12‐dodecanediol) were extracted from the reaction mixtures using tetrahydrofurane and precipitated from tetrahydrofurane— iso ‐hexane (1:1, v/v) at ∼0°C. The precipitate of poly(3,3′‐thiodipropionic acid‐ co ‐1,6‐hexanediol) showed a maximum molecular weight of 6 × 10 5 Da corresponding to a M W of ∼24,200 Da and a degree of polymerization of up to 2,150 monomer units. The precipitated poly(3,3′‐thiodipropionic acid‐ co ‐1,12‐dodecanediol) showed a maximum molecular weight of 8 × 10 5 Da corresponding to a M W of ∼27,200 Da and a maximum degree of polymerization of up to 2,200 monomer units. The chemical structures of both polyesters containing thioether functions were confirmed by chemical derivatization and NMR spectrometry. The chemical structures of various low‐molecular weight reaction intermediates of the esterification of 3,3′‐thiodipropionic acid with 1,6‐hexanediol were elucidated by GC–MS. Biotechnol. Bioeng. 2008;99: 1074–1084. © 2007 Wiley Periodicals, Inc. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library Biotechnology and Bioengineering 99 5 1074 1084 |
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English |
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Abstract Linear copolymeric polyesters (polyoxoesters) containing thioether functions [poly(3,3′‐thiodipropionic acid‐ co ‐α,ω‐alkanediols)] were formed in good yield by esterification of an equimolar mixture of 3,3′‐thiodipropionic acid (4‐thiaheptane‐1,7‐dioic acid) and 1,6‐hexanediol (weight average molecular mass, M W >600 Da: ∼81% after 6 h) or 1,12‐dodecanediol ( M W > 900 Da: ∼90% after 6 h) catalyzed by immobilized lipase B from Candida antarctica (Novozym 435) for up to 336 h in moderate vacuo without a solvent or drying reagent in the reaction mixture. Poly (3,3′‐thiodipropionic acid‐ co ‐1,6‐hexanediol) and poly (3,3′‐thiodipropionic acid‐ co ‐1,12‐dodecanediol) were extracted from the reaction mixtures using tetrahydrofurane and precipitated from tetrahydrofurane— iso ‐hexane (1:1, v/v) at ∼0°C. The precipitate of poly(3,3′‐thiodipropionic acid‐ co ‐1,6‐hexanediol) showed a maximum molecular weight of 6 × 10 5 Da corresponding to a M W of ∼24,200 Da and a degree of polymerization of up to 2,150 monomer units. The precipitated poly(3,3′‐thiodipropionic acid‐ co ‐1,12‐dodecanediol) showed a maximum molecular weight of 8 × 10 5 Da corresponding to a M W of ∼27,200 Da and a maximum degree of polymerization of up to 2,200 monomer units. The chemical structures of both polyesters containing thioether functions were confirmed by chemical derivatization and NMR spectrometry. The chemical structures of various low‐molecular weight reaction intermediates of the esterification of 3,3′‐thiodipropionic acid with 1,6‐hexanediol were elucidated by GC–MS. Biotechnol. Bioeng. 2008;99: 1074–1084. © 2007 Wiley Periodicals, Inc. |
format |
Article in Journal/Newspaper |
author |
Fehling, E. Klein, E. Vosmann, K. Bergander, K. Weber, N. |
spellingShingle |
Fehling, E. Klein, E. Vosmann, K. Bergander, K. Weber, N. Linear copolymeric poly(thia‐alkanedioates) by lipase‐catalyzed esterification and transesterification of 3,3′‐thiodipropionic acid and its dimethyl ester with α,ω‐alkanediols |
author_facet |
Fehling, E. Klein, E. Vosmann, K. Bergander, K. Weber, N. |
author_sort |
Fehling, E. |
title |
Linear copolymeric poly(thia‐alkanedioates) by lipase‐catalyzed esterification and transesterification of 3,3′‐thiodipropionic acid and its dimethyl ester with α,ω‐alkanediols |
title_short |
Linear copolymeric poly(thia‐alkanedioates) by lipase‐catalyzed esterification and transesterification of 3,3′‐thiodipropionic acid and its dimethyl ester with α,ω‐alkanediols |
title_full |
Linear copolymeric poly(thia‐alkanedioates) by lipase‐catalyzed esterification and transesterification of 3,3′‐thiodipropionic acid and its dimethyl ester with α,ω‐alkanediols |
title_fullStr |
Linear copolymeric poly(thia‐alkanedioates) by lipase‐catalyzed esterification and transesterification of 3,3′‐thiodipropionic acid and its dimethyl ester with α,ω‐alkanediols |
title_full_unstemmed |
Linear copolymeric poly(thia‐alkanedioates) by lipase‐catalyzed esterification and transesterification of 3,3′‐thiodipropionic acid and its dimethyl ester with α,ω‐alkanediols |
title_sort |
linear copolymeric poly(thia‐alkanedioates) by lipase‐catalyzed esterification and transesterification of 3,3′‐thiodipropionic acid and its dimethyl ester with α,ω‐alkanediols |
publisher |
Wiley |
publishDate |
2007 |
url |
http://dx.doi.org/10.1002/bit.21704 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fbit.21704 https://onlinelibrary.wiley.com/doi/pdf/10.1002/bit.21704 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Biotechnology and Bioengineering volume 99, issue 5, page 1074-1084 ISSN 0006-3592 1097-0290 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/bit.21704 |
container_title |
Biotechnology and Bioengineering |
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99 |
container_issue |
5 |
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1074 |
op_container_end_page |
1084 |
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1800741458446123008 |