Lipase-catalyzed synthesis of oligoesters of 2,5-furandicarboxylic acid with aliphatic diols
Abstract 2,5-Furandicarboxylic acid is a platform chemical for the production of biobased polymers and materials. This study reports the synthesis of furan oligoesters via polytransesterification of dimethyl furan-2,5-dicarboxylate and linear α, ω-aliphatic diols with chain length ranging from C2 to...
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Walter de Gruyter GmbH
2015
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crdegruyter:10.1515/pac-2014-1003 2024-09-15T17:40:49+00:00 Lipase-catalyzed synthesis of oligoesters of 2,5-furandicarboxylic acid with aliphatic diols Cruz-Izquierdo, Álvaro van den Broek, Lambertus A.M. Serra, Juan L. Llama, María J. Boeriu, Carmen G. 2015 http://dx.doi.org/10.1515/pac-2014-1003 https://www.degruyter.com/view/journals/pac/87/1/article-p59.xml https://www.degruyter.com/document/doi/10.1515/pac-2014-1003/xml https://www.degruyter.com/document/doi/10.1515/pac-2014-1003/pdf en eng Walter de Gruyter GmbH Pure and Applied Chemistry volume 87, issue 1, page 59-69 ISSN 1365-3075 0033-4545 journal-article 2015 crdegruyter https://doi.org/10.1515/pac-2014-1003 2024-08-12T04:09:11Z Abstract 2,5-Furandicarboxylic acid is a platform chemical for the production of biobased polymers and materials. This study reports the synthesis of furan oligoesters via polytransesterification of dimethyl furan-2,5-dicarboxylate and linear α, ω-aliphatic diols with chain length ranging from C2 to C12, using immobilized lipase B from Candida antarctica (Novozym 435) in dry organic solvents. Dimethyl furan-2,5-dicarboxylic acid (A) and 1,4-butanediol (B) were used as model substrates under different conditions producing a mixture of cyclic (CEOs) and linear (LEOs) ester oligomers up to decamers and dodecamers, respectively, with high yield. The size of the oligomers and distribution of the products is controlled by the initial concentration of substrates and temperature. While the shortest CEOs are the main cyclic compounds at 20 mM, the longest CEOs are formed at 175 mM. The chain length of the aliphatic diol co-monomers strongly influences the yield and the type of oligoesters formed. High substrate conversion of 90–95 % was obtained for C4–C12 diols, while in the case of ethylene glycol and 1,3-propanediol the conversion was moderate (i.e., 75 %). The product of the reaction between dimethyl furan-2,5-dicarboxylate and ethylene glycol (C2) and 1,3-propanediol (C3), respectively, consisted only of linear oligoesters. Longer oligoesters were obtained for alkyl chains higher than C4. The chain length and the abundance of oligoesters increases in the order: C2<C12<C10<C3<C8<C4 <C6. No substrate or product inhibition was observed in the production of furan-based oligoesters. The present biobased oligoesters are obtained via a green process and have potential application as macromonomers. Article in Journal/Newspaper Antarc* Antarctica De Gruyter Pure and Applied Chemistry 87 1 59 69 |
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English |
description |
Abstract 2,5-Furandicarboxylic acid is a platform chemical for the production of biobased polymers and materials. This study reports the synthesis of furan oligoesters via polytransesterification of dimethyl furan-2,5-dicarboxylate and linear α, ω-aliphatic diols with chain length ranging from C2 to C12, using immobilized lipase B from Candida antarctica (Novozym 435) in dry organic solvents. Dimethyl furan-2,5-dicarboxylic acid (A) and 1,4-butanediol (B) were used as model substrates under different conditions producing a mixture of cyclic (CEOs) and linear (LEOs) ester oligomers up to decamers and dodecamers, respectively, with high yield. The size of the oligomers and distribution of the products is controlled by the initial concentration of substrates and temperature. While the shortest CEOs are the main cyclic compounds at 20 mM, the longest CEOs are formed at 175 mM. The chain length of the aliphatic diol co-monomers strongly influences the yield and the type of oligoesters formed. High substrate conversion of 90–95 % was obtained for C4–C12 diols, while in the case of ethylene glycol and 1,3-propanediol the conversion was moderate (i.e., 75 %). The product of the reaction between dimethyl furan-2,5-dicarboxylate and ethylene glycol (C2) and 1,3-propanediol (C3), respectively, consisted only of linear oligoesters. Longer oligoesters were obtained for alkyl chains higher than C4. The chain length and the abundance of oligoesters increases in the order: C2<C12<C10<C3<C8<C4 <C6. No substrate or product inhibition was observed in the production of furan-based oligoesters. The present biobased oligoesters are obtained via a green process and have potential application as macromonomers. |
format |
Article in Journal/Newspaper |
author |
Cruz-Izquierdo, Álvaro van den Broek, Lambertus A.M. Serra, Juan L. Llama, María J. Boeriu, Carmen G. |
spellingShingle |
Cruz-Izquierdo, Álvaro van den Broek, Lambertus A.M. Serra, Juan L. Llama, María J. Boeriu, Carmen G. Lipase-catalyzed synthesis of oligoesters of 2,5-furandicarboxylic acid with aliphatic diols |
author_facet |
Cruz-Izquierdo, Álvaro van den Broek, Lambertus A.M. Serra, Juan L. Llama, María J. Boeriu, Carmen G. |
author_sort |
Cruz-Izquierdo, Álvaro |
title |
Lipase-catalyzed synthesis of oligoesters of 2,5-furandicarboxylic acid with aliphatic diols |
title_short |
Lipase-catalyzed synthesis of oligoesters of 2,5-furandicarboxylic acid with aliphatic diols |
title_full |
Lipase-catalyzed synthesis of oligoesters of 2,5-furandicarboxylic acid with aliphatic diols |
title_fullStr |
Lipase-catalyzed synthesis of oligoesters of 2,5-furandicarboxylic acid with aliphatic diols |
title_full_unstemmed |
Lipase-catalyzed synthesis of oligoesters of 2,5-furandicarboxylic acid with aliphatic diols |
title_sort |
lipase-catalyzed synthesis of oligoesters of 2,5-furandicarboxylic acid with aliphatic diols |
publisher |
Walter de Gruyter GmbH |
publishDate |
2015 |
url |
http://dx.doi.org/10.1515/pac-2014-1003 https://www.degruyter.com/view/journals/pac/87/1/article-p59.xml https://www.degruyter.com/document/doi/10.1515/pac-2014-1003/xml https://www.degruyter.com/document/doi/10.1515/pac-2014-1003/pdf |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Pure and Applied Chemistry volume 87, issue 1, page 59-69 ISSN 1365-3075 0033-4545 |
op_doi |
https://doi.org/10.1515/pac-2014-1003 |
container_title |
Pure and Applied Chemistry |
container_volume |
87 |
container_issue |
1 |
container_start_page |
59 |
op_container_end_page |
69 |
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1810486860057673728 |