Enzymatic Transesterification of Kraft Lignin with Long Acyl Chains in Ionic Liquids
Valorization of lignin is essential for the economic viability of the biorefinery concept. For example, the enhancement of lignin hydrophobicity by chemical esterification is known to improve its miscibility in apolar polyolefin matrices, thereby helping the production of bio-based composites. To th...
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ftpubmed:oai:pubmedcentral.nih.gov:6332217 2023-05-15T13:36:39+02:00 Enzymatic Transesterification of Kraft Lignin with Long Acyl Chains in Ionic Liquids Hulin, Lise Husson, Eric Bonnet, Jean-Pierre Stevanovic, Tatjana Sarazin, Catherine 2015-09-09 http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6332217/ http://www.ncbi.nlm.nih.gov/pubmed/26370956 https://doi.org/10.3390/molecules200916334 en eng MDPI http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6332217/ http://www.ncbi.nlm.nih.gov/pubmed/26370956 http://dx.doi.org/10.3390/molecules200916334 © 2015 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/). CC-BY Article Text 2015 ftpubmed https://doi.org/10.3390/molecules200916334 2019-01-27T01:31:34Z Valorization of lignin is essential for the economic viability of the biorefinery concept. For example, the enhancement of lignin hydrophobicity by chemical esterification is known to improve its miscibility in apolar polyolefin matrices, thereby helping the production of bio-based composites. To this end and due to its many reactive hydroxyl groups, lignin is a challenging macromolecular substrate for biocatalyzed esterification in non-conventional media. The present work describes for the first time the lipase-catalyzed transesterification of Kraft lignin in ionic liquids (ILs). Three lipases, three 1-butyl-3-methylimidazolium based ILs and ethyl oleate as long chain acyl donor were selected. Best results were obtained with a hydrophilic/hydrophobic binary IL system (1-butyl-3-methylimidazolium trifluoromethanesulfonate/1-butyl-3-methylimidazolium hexafluoro- phosphate, 1/1 v/v) and the immobilized lipase B from Candida antarctica (CALB) that afforded a promising transesterification yield (ca. 30%). Similar performances were achieved by using 1-butyl-3-methylimidazolium hexafluorophosphate as a coating agent for CALB rather than as a co-solvent in 1-butyl-3-methylimidazolium trifluoromethane-sulfonate thus limiting the use of hydrophobic IL. Structural characterization of lignin oleate was performed by spectroscopic studies (FTIR and 1H-NMR). The synthesized lignin oleate exhibited interesting thermal and textural properties, different from those of the original Kraft lignin. Text Antarc* Antarctica PubMed Central (PMC) Molecules 20 9 16334 16353 |
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Article Hulin, Lise Husson, Eric Bonnet, Jean-Pierre Stevanovic, Tatjana Sarazin, Catherine Enzymatic Transesterification of Kraft Lignin with Long Acyl Chains in Ionic Liquids |
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Valorization of lignin is essential for the economic viability of the biorefinery concept. For example, the enhancement of lignin hydrophobicity by chemical esterification is known to improve its miscibility in apolar polyolefin matrices, thereby helping the production of bio-based composites. To this end and due to its many reactive hydroxyl groups, lignin is a challenging macromolecular substrate for biocatalyzed esterification in non-conventional media. The present work describes for the first time the lipase-catalyzed transesterification of Kraft lignin in ionic liquids (ILs). Three lipases, three 1-butyl-3-methylimidazolium based ILs and ethyl oleate as long chain acyl donor were selected. Best results were obtained with a hydrophilic/hydrophobic binary IL system (1-butyl-3-methylimidazolium trifluoromethanesulfonate/1-butyl-3-methylimidazolium hexafluoro- phosphate, 1/1 v/v) and the immobilized lipase B from Candida antarctica (CALB) that afforded a promising transesterification yield (ca. 30%). Similar performances were achieved by using 1-butyl-3-methylimidazolium hexafluorophosphate as a coating agent for CALB rather than as a co-solvent in 1-butyl-3-methylimidazolium trifluoromethane-sulfonate thus limiting the use of hydrophobic IL. Structural characterization of lignin oleate was performed by spectroscopic studies (FTIR and 1H-NMR). The synthesized lignin oleate exhibited interesting thermal and textural properties, different from those of the original Kraft lignin. |
format |
Text |
author |
Hulin, Lise Husson, Eric Bonnet, Jean-Pierre Stevanovic, Tatjana Sarazin, Catherine |
author_facet |
Hulin, Lise Husson, Eric Bonnet, Jean-Pierre Stevanovic, Tatjana Sarazin, Catherine |
author_sort |
Hulin, Lise |
title |
Enzymatic Transesterification of Kraft Lignin with Long Acyl Chains in Ionic Liquids |
title_short |
Enzymatic Transesterification of Kraft Lignin with Long Acyl Chains in Ionic Liquids |
title_full |
Enzymatic Transesterification of Kraft Lignin with Long Acyl Chains in Ionic Liquids |
title_fullStr |
Enzymatic Transesterification of Kraft Lignin with Long Acyl Chains in Ionic Liquids |
title_full_unstemmed |
Enzymatic Transesterification of Kraft Lignin with Long Acyl Chains in Ionic Liquids |
title_sort |
enzymatic transesterification of kraft lignin with long acyl chains in ionic liquids |
publisher |
MDPI |
publishDate |
2015 |
url |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6332217/ http://www.ncbi.nlm.nih.gov/pubmed/26370956 https://doi.org/10.3390/molecules200916334 |
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Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6332217/ http://www.ncbi.nlm.nih.gov/pubmed/26370956 http://dx.doi.org/10.3390/molecules200916334 |
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© 2015 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/). |
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CC-BY |
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https://doi.org/10.3390/molecules200916334 |
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Molecules |
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20 |
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9 |
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16334 |
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16353 |
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