Ferulic Acid as Building Block for the Lipase-Catalyzed Synthesis of Biobased Aromatic Polyesters

Enzymatic synthesis of aromatic biobased polyesters is a recent and rapidly expanding research field. However, the direct lipase-catalyzed synthesis of polyesters from ferulic acid has not yet been reported. In this work, various ferulic-based monomers were considered for their capability to undergo...

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Autores principales:	Alfred Bazin, Luc Avérous, Eric Pollet
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	<i>Candida antarctica</i> lipase B ferulic acid semi-aromatic polyesters biobased enzymatic polymerization Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/796d1b581d334326b120612a5a185ec8
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spelling	oai:doaj.org-article:796d1b581d334326b120612a5a185ec82021-11-11T18:44:07ZFerulic Acid as Building Block for the Lipase-Catalyzed Synthesis of Biobased Aromatic Polyesters10.3390/polym132136932073-4360https://doaj.org/article/796d1b581d334326b120612a5a185ec82021-10-01T00:00:00Zhttps://www.mdpi.com/2073-4360/13/21/3693https://doaj.org/toc/2073-4360Enzymatic synthesis of aromatic biobased polyesters is a recent and rapidly expanding research field. However, the direct lipase-catalyzed synthesis of polyesters from ferulic acid has not yet been reported. In this work, various ferulic-based monomers were considered for their capability to undergo CALB-catalyzed polymerization. After conversion into diesters of different lengths, the CALB-catalyzed polymerization of these monomers with 1,4-butanediol resulted in short oligomers with a DP<sub>n</sub> up to 5. Hydrogenation of the double bond resulted in monomers allowing obtaining polyesters of higher molar masses with DP<sub>n</sub> up to 58 and M<sub>w</sub> up to 33,100 g·mol<sup>−1</sup>. These polyesters presented good thermal resistance up to 350 °C and T<sub>g</sub> up to 7 °C. Reduction of the ferulic-based diesters into diols allowed preserving the double bond and synthesizing polyesters with a DP<sub>n</sub> up to 19 and M<sub>w</sub> up to 15,500 g·mol<sup>−1</sup> and higher T<sub>g</sub> (up to 21 °C). Thus, this study has shown that the monomer hydrogenation strategy proved to be the most promising route to achieve ferulic-based polyester chains of high DP<sub>n</sub>. This study also demonstrates for the first time that ferulic-based diols allow the synthesis of high T<sub>g</sub> polyesters. Therefore, this is an important first step toward the synthesis of competitive biobased aromatic polyesters by enzymatic catalysis.Alfred BazinLuc AvérousEric PolletMDPI AGarticle<i>Candida antarctica</i> lipase Bferulic acidsemi-aromatic polyestersbiobasedenzymatic polymerizationOrganic chemistryQD241-441ENPolymers, Vol 13, Iss 3693, p 3693 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	<i>Candida antarctica</i> lipase B ferulic acid semi-aromatic polyesters biobased enzymatic polymerization Organic chemistry QD241-441
spellingShingle	<i>Candida antarctica</i> lipase B ferulic acid semi-aromatic polyesters biobased enzymatic polymerization Organic chemistry QD241-441 Alfred Bazin Luc Avérous Eric Pollet Ferulic Acid as Building Block for the Lipase-Catalyzed Synthesis of Biobased Aromatic Polyesters
description	Enzymatic synthesis of aromatic biobased polyesters is a recent and rapidly expanding research field. However, the direct lipase-catalyzed synthesis of polyesters from ferulic acid has not yet been reported. In this work, various ferulic-based monomers were considered for their capability to undergo CALB-catalyzed polymerization. After conversion into diesters of different lengths, the CALB-catalyzed polymerization of these monomers with 1,4-butanediol resulted in short oligomers with a DP<sub>n</sub> up to 5. Hydrogenation of the double bond resulted in monomers allowing obtaining polyesters of higher molar masses with DP<sub>n</sub> up to 58 and M<sub>w</sub> up to 33,100 g·mol<sup>−1</sup>. These polyesters presented good thermal resistance up to 350 °C and T<sub>g</sub> up to 7 °C. Reduction of the ferulic-based diesters into diols allowed preserving the double bond and synthesizing polyesters with a DP<sub>n</sub> up to 19 and M<sub>w</sub> up to 15,500 g·mol<sup>−1</sup> and higher T<sub>g</sub> (up to 21 °C). Thus, this study has shown that the monomer hydrogenation strategy proved to be the most promising route to achieve ferulic-based polyester chains of high DP<sub>n</sub>. This study also demonstrates for the first time that ferulic-based diols allow the synthesis of high T<sub>g</sub> polyesters. Therefore, this is an important first step toward the synthesis of competitive biobased aromatic polyesters by enzymatic catalysis.
format	article
author	Alfred Bazin Luc Avérous Eric Pollet
author_facet	Alfred Bazin Luc Avérous Eric Pollet
author_sort	Alfred Bazin
title	Ferulic Acid as Building Block for the Lipase-Catalyzed Synthesis of Biobased Aromatic Polyesters
title_short	Ferulic Acid as Building Block for the Lipase-Catalyzed Synthesis of Biobased Aromatic Polyesters
title_full	Ferulic Acid as Building Block for the Lipase-Catalyzed Synthesis of Biobased Aromatic Polyesters
title_fullStr	Ferulic Acid as Building Block for the Lipase-Catalyzed Synthesis of Biobased Aromatic Polyesters
title_full_unstemmed	Ferulic Acid as Building Block for the Lipase-Catalyzed Synthesis of Biobased Aromatic Polyesters
title_sort	ferulic acid as building block for the lipase-catalyzed synthesis of biobased aromatic polyesters
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/796d1b581d334326b120612a5a185ec8
work_keys_str_mv	AT alfredbazin ferulicacidasbuildingblockforthelipasecatalyzedsynthesisofbiobasedaromaticpolyesters AT lucaverous ferulicacidasbuildingblockforthelipasecatalyzedsynthesisofbiobasedaromaticpolyesters AT ericpollet ferulicacidasbuildingblockforthelipasecatalyzedsynthesisofbiobasedaromaticpolyesters
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Ferulic Acid as Building Block for the Lipase-Catalyzed Synthesis of Biobased Aromatic Polyesters

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