Enzymatic synthesis and characterization of novel terpolymers from renewable sources
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 bioca...
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ftunivwagenin:oai:library.wur.nl:wurpubs/544913 2024-01-28T10:00:36+01:00 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 2019 text/html https://research.wur.nl/en/publications/enzymatic-synthesis-and-characterization-of-novel-terpolymers-fro https://doi.org/10.1515/pac-2018-1015 en eng https://edepot.wur.nl/467239 https://research.wur.nl/en/publications/enzymatic-synthesis-and-characterization-of-novel-terpolymers-fro doi:10.1515/pac-2018-1015 info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-nd/4.0/ Wageningen University & Research Pure and Applied Chemistry 91 (2019) 3 ISSN: 0033-4545 POC-2018 biobased terpolymer biocatalysis dimethyl furan-2,5-dicarboxylate dimethyl itaconate lipase info:eu-repo/semantics/article Article/Letter to editor info:eu-repo/semantics/publishedVersion 2019 ftunivwagenin https://doi.org/10.1515/pac-2018-1015 2024-01-03T23:15:04Z 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 (Mn, 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 Wageningen UR (University & Research Centre): Digital Library Pure and Applied Chemistry 91 3 397 408 |
institution |
Open Polar |
collection |
Wageningen UR (University & Research Centre): Digital Library |
op_collection_id |
ftunivwagenin |
language |
English |
topic |
POC-2018 biobased terpolymer biocatalysis dimethyl furan-2,5-dicarboxylate dimethyl itaconate lipase |
spellingShingle |
POC-2018 biobased terpolymer biocatalysis dimethyl furan-2,5-dicarboxylate dimethyl itaconate lipase 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 |
topic_facet |
POC-2018 biobased terpolymer biocatalysis dimethyl furan-2,5-dicarboxylate dimethyl itaconate lipase |
description |
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 (Mn, 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 |
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 |
publishDate |
2019 |
url |
https://research.wur.nl/en/publications/enzymatic-synthesis-and-characterization-of-novel-terpolymers-fro https://doi.org/10.1515/pac-2018-1015 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Pure and Applied Chemistry 91 (2019) 3 ISSN: 0033-4545 |
op_relation |
https://edepot.wur.nl/467239 https://research.wur.nl/en/publications/enzymatic-synthesis-and-characterization-of-novel-terpolymers-fro doi:10.1515/pac-2018-1015 |
op_rights |
info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-nd/4.0/ Wageningen University & Research |
op_doi |
https://doi.org/10.1515/pac-2018-1015 |
container_title |
Pure and Applied Chemistry |
container_volume |
91 |
container_issue |
3 |
container_start_page |
397 |
op_container_end_page |
408 |
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1789325070232977408 |