Enzymatic synthesis and characterization of novel terpolymers from renewable sources
Abstract 2,5-Furandicarboxylic acid and itaconic acid are both important biobased platform chemicals and their terpolymer with 1,6-hexanediol (HDO) can be the starting point for a new class of reactive polyesters, with important applications. The green synthetic route developed in this study involve...
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Walter de Gruyter GmbH
2018
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crdegruyter:10.1515/pac-2018-1015 2024-09-15T17:46:41+00:00 Enzymatic synthesis and characterization of novel terpolymers from renewable sources Aparaschivei, Diana Todea, Anamaria Frissen, August E. Badea, Valentin Rusu, Gerlinde Sisu, Eugen Puiu, Maria Boeriu, Carmen G. Peter, Francisc 2018 http://dx.doi.org/10.1515/pac-2018-1015 http://www.degruyter.com/view/j/pac.2019.91.issue-3/pac-2018-1015/pac-2018-1015.xml https://www.degruyter.com/document/doi/10.1515/pac-2018-1015/xml https://www.degruyter.com/document/doi/10.1515/pac-2018-1015/pdf en eng Walter de Gruyter GmbH Pure and Applied Chemistry volume 91, issue 3, page 397-408 ISSN 1365-3075 0033-4545 journal-article 2018 crdegruyter https://doi.org/10.1515/pac-2018-1015 2024-07-15T04:11:29Z Abstract 2,5-Furandicarboxylic acid and itaconic acid are both important biobased platform chemicals and their terpolymer with 1,6-hexanediol (HDO) can be the starting point for a new class of reactive polyesters, with important applications. The green synthetic route developed in this study involves a biocatalytic condensation polymerization reaction of dimethyl furan-2,5-dicarboxylate (DMFDC) and dimethyl itaconate (DMI) with HDO in toluene at 80°C, using commercial immobilized lipases from Candida antarctica B. In the best conditions, the formed polymer product was isolated with more than 80% yield, containing about 85% terpolymer with average molecular mass of about 1200 (M n , calculated from MALDI-TOF MS data) and 15% DMFDC_HDO copolymer. Considering the higher reactivity of DMFDC, the composition of the synthesized polymer can be directed by adjusting the molar ratio of DMFDC and DMI, as well as by extending the reaction time. Structural analysis by NMR demonstrated the regioselective preference for the carbonyl group from DMI adjacent to the methylene group. The biocatalyst was successfully reused in multiple reaction cycles. Article in Journal/Newspaper Antarc* Antarctica De Gruyter Pure and Applied Chemistry 91 3 397 408 |
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English |
description |
Abstract 2,5-Furandicarboxylic acid and itaconic acid are both important biobased platform chemicals and their terpolymer with 1,6-hexanediol (HDO) can be the starting point for a new class of reactive polyesters, with important applications. The green synthetic route developed in this study involves a biocatalytic condensation polymerization reaction of dimethyl furan-2,5-dicarboxylate (DMFDC) and dimethyl itaconate (DMI) with HDO in toluene at 80°C, using commercial immobilized lipases from Candida antarctica B. In the best conditions, the formed polymer product was isolated with more than 80% yield, containing about 85% terpolymer with average molecular mass of about 1200 (M n , calculated from MALDI-TOF MS data) and 15% DMFDC_HDO copolymer. Considering the higher reactivity of DMFDC, the composition of the synthesized polymer can be directed by adjusting the molar ratio of DMFDC and DMI, as well as by extending the reaction time. Structural analysis by NMR demonstrated the regioselective preference for the carbonyl group from DMI adjacent to the methylene group. The biocatalyst was successfully reused in multiple reaction cycles. |
format |
Article in Journal/Newspaper |
author |
Aparaschivei, Diana Todea, Anamaria Frissen, August E. Badea, Valentin Rusu, Gerlinde Sisu, Eugen Puiu, Maria Boeriu, Carmen G. Peter, Francisc |
spellingShingle |
Aparaschivei, Diana Todea, Anamaria Frissen, August E. Badea, Valentin Rusu, Gerlinde Sisu, Eugen Puiu, Maria Boeriu, Carmen G. Peter, Francisc Enzymatic synthesis and characterization of novel terpolymers from renewable sources |
author_facet |
Aparaschivei, Diana Todea, Anamaria Frissen, August E. Badea, Valentin Rusu, Gerlinde Sisu, Eugen Puiu, Maria Boeriu, Carmen G. Peter, Francisc |
author_sort |
Aparaschivei, Diana |
title |
Enzymatic synthesis and characterization of novel terpolymers from renewable sources |
title_short |
Enzymatic synthesis and characterization of novel terpolymers from renewable sources |
title_full |
Enzymatic synthesis and characterization of novel terpolymers from renewable sources |
title_fullStr |
Enzymatic synthesis and characterization of novel terpolymers from renewable sources |
title_full_unstemmed |
Enzymatic synthesis and characterization of novel terpolymers from renewable sources |
title_sort |
enzymatic synthesis and characterization of novel terpolymers from renewable sources |
publisher |
Walter de Gruyter GmbH |
publishDate |
2018 |
url |
http://dx.doi.org/10.1515/pac-2018-1015 http://www.degruyter.com/view/j/pac.2019.91.issue-3/pac-2018-1015/pac-2018-1015.xml https://www.degruyter.com/document/doi/10.1515/pac-2018-1015/xml https://www.degruyter.com/document/doi/10.1515/pac-2018-1015/pdf |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Pure and Applied Chemistry volume 91, issue 3, page 397-408 ISSN 1365-3075 0033-4545 |
op_doi |
https://doi.org/10.1515/pac-2018-1015 |
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Pure and Applied Chemistry |
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91 |
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3 |
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397 |
op_container_end_page |
408 |
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1810495012386897920 |