Enzymatic synthesis of biobased aliphatic-aromatic oligoesters using 5,5′-bis(hydroxymethyl)furoin as a building block
5,5′-Dihydroxymethyl furoin (DHMF) is a novel biobased difuranic polyol scaffold, achievable from the benzoin condensation of 5-hydroxymethylfurfural (HMF), which has recently been employed as a monomer for the preparation of cross-linked polyesters and polyurethane. Its upgrading by means of enzyma...
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ftunivferrarair:oai:sfera.unife.it:11392/2409568 2024-04-14T08:02:25+00:00 Enzymatic synthesis of biobased aliphatic-aromatic oligoesters using 5,5′-bis(hydroxymethyl)furoin as a building block Baraldi S. Fantin G. Di Carmine G. Ragno D. Brandolese A. Massi A. Bortolini O. Marchetti N. Giovannini P. P. Baraldi, S. Fantin, G. Di Carmine, G. Ragno, D. Brandolese, A. Massi, A. Bortolini, O. Marchetti, N. Giovannini, P. P. 2019 ELETTRONICO http://hdl.handle.net/11392/2409568 https://doi.org/10.1039/c9ra06621g https://pubs.rsc.org/en/content/articlelanding/2019/RA/C9RA06621G#!divAbstract eng eng info:eu-repo/semantics/altIdentifier/wos/WOS:000487104200016 volume:9 issue:50 firstpage:29044 lastpage:29050 numberofpages:7 journal:RSC ADVANCES http://hdl.handle.net/11392/2409568 doi:10.1039/c9ra06621g info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-85072514672 https://pubs.rsc.org/en/content/articlelanding/2019/RA/C9RA06621G#!divAbstract info:eu-repo/semantics/openAccess info:eu-repo/semantics/article 2019 ftunivferrarair https://doi.org/10.1039/c9ra06621g 2024-03-21T17:50:54Z 5,5′-Dihydroxymethyl furoin (DHMF) is a novel biobased difuranic polyol scaffold, achievable from the benzoin condensation of 5-hydroxymethylfurfural (HMF), which has recently been employed as a monomer for the preparation of cross-linked polyesters and polyurethane. Its upgrading by means of enzymatic reactions has not yet been reported. Here we demonstrated that Candida antarctica lipase B (CALB) is a suitable biocatalyst for the selective esterification of the primary hydroxyl groups of DHMF. Exploiting this enzymatic activity, DHMF has been reacted with the diethyl esters of succinic and sebacic acids obtaining fully biobased linear oligoesters with number-average molecular weight around 1000 g mol-1 and free hydroxyl groups on the polymer backbone. The structures of the DHMF-diacid ethyl ester dimers and of the oligomers were elucidated by NMR and MS analyses. Article in Journal/Newspaper Antarc* Antarctica Università degli Studi di Ferrara: CINECA IRIS RSC Advances 9 50 29044 29050 |
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Open Polar |
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Università degli Studi di Ferrara: CINECA IRIS |
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ftunivferrarair |
language |
English |
description |
5,5′-Dihydroxymethyl furoin (DHMF) is a novel biobased difuranic polyol scaffold, achievable from the benzoin condensation of 5-hydroxymethylfurfural (HMF), which has recently been employed as a monomer for the preparation of cross-linked polyesters and polyurethane. Its upgrading by means of enzymatic reactions has not yet been reported. Here we demonstrated that Candida antarctica lipase B (CALB) is a suitable biocatalyst for the selective esterification of the primary hydroxyl groups of DHMF. Exploiting this enzymatic activity, DHMF has been reacted with the diethyl esters of succinic and sebacic acids obtaining fully biobased linear oligoesters with number-average molecular weight around 1000 g mol-1 and free hydroxyl groups on the polymer backbone. The structures of the DHMF-diacid ethyl ester dimers and of the oligomers were elucidated by NMR and MS analyses. |
author2 |
Baraldi, S. Fantin, G. Di Carmine, G. Ragno, D. Brandolese, A. Massi, A. Bortolini, O. Marchetti, N. Giovannini, P. P. |
format |
Article in Journal/Newspaper |
author |
Baraldi S. Fantin G. Di Carmine G. Ragno D. Brandolese A. Massi A. Bortolini O. Marchetti N. Giovannini P. P. |
spellingShingle |
Baraldi S. Fantin G. Di Carmine G. Ragno D. Brandolese A. Massi A. Bortolini O. Marchetti N. Giovannini P. P. Enzymatic synthesis of biobased aliphatic-aromatic oligoesters using 5,5′-bis(hydroxymethyl)furoin as a building block |
author_facet |
Baraldi S. Fantin G. Di Carmine G. Ragno D. Brandolese A. Massi A. Bortolini O. Marchetti N. Giovannini P. P. |
author_sort |
Baraldi S. |
title |
Enzymatic synthesis of biobased aliphatic-aromatic oligoesters using 5,5′-bis(hydroxymethyl)furoin as a building block |
title_short |
Enzymatic synthesis of biobased aliphatic-aromatic oligoesters using 5,5′-bis(hydroxymethyl)furoin as a building block |
title_full |
Enzymatic synthesis of biobased aliphatic-aromatic oligoesters using 5,5′-bis(hydroxymethyl)furoin as a building block |
title_fullStr |
Enzymatic synthesis of biobased aliphatic-aromatic oligoesters using 5,5′-bis(hydroxymethyl)furoin as a building block |
title_full_unstemmed |
Enzymatic synthesis of biobased aliphatic-aromatic oligoesters using 5,5′-bis(hydroxymethyl)furoin as a building block |
title_sort |
enzymatic synthesis of biobased aliphatic-aromatic oligoesters using 5,5′-bis(hydroxymethyl)furoin as a building block |
publishDate |
2019 |
url |
http://hdl.handle.net/11392/2409568 https://doi.org/10.1039/c9ra06621g https://pubs.rsc.org/en/content/articlelanding/2019/RA/C9RA06621G#!divAbstract |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
info:eu-repo/semantics/altIdentifier/wos/WOS:000487104200016 volume:9 issue:50 firstpage:29044 lastpage:29050 numberofpages:7 journal:RSC ADVANCES http://hdl.handle.net/11392/2409568 doi:10.1039/c9ra06621g info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-85072514672 https://pubs.rsc.org/en/content/articlelanding/2019/RA/C9RA06621G#!divAbstract |
op_rights |
info:eu-repo/semantics/openAccess |
op_doi |
https://doi.org/10.1039/c9ra06621g |
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RSC Advances |
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9 |
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50 |
container_start_page |
29044 |
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29050 |
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1796314827340120064 |