Enzymatic transesterification of kraft lignin with long acyl chains in ionic liquids
International audience 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-...
Published in: | Molecules |
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Main Authors: | , , , , |
Other Authors: | , , , , , , , , , , , , , , , , , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
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HAL CCSD
2015
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Online Access: | https://hal.science/hal-01344626 https://hal.science/hal-01344626/document https://hal.science/hal-01344626/file/molecules-20-16334.pdf https://doi.org/10.3390/molecules200916334 |
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ftunivpicardie:oai:HAL:hal-01344626v1 |
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record_format |
openpolar |
institution |
Open Polar |
collection |
Université de Picardie Jules Verne |
op_collection_id |
ftunivpicardie |
language |
English |
topic |
lignin enzymatic esterification lipase ionic liquids [SDV]Life Sciences [q-bio] [CHIM]Chemical Sciences |
spellingShingle |
lignin enzymatic esterification lipase ionic liquids [SDV]Life Sciences [q-bio] [CHIM]Chemical Sciences Hulin, L. Husson, E. Bonnet, Jean-Pierre Stevanovic, T. Sarazin, C. Enzymatic transesterification of kraft lignin with long acyl chains in ionic liquids |
topic_facet |
lignin enzymatic esterification lipase ionic liquids [SDV]Life Sciences [q-bio] [CHIM]Chemical Sciences |
description |
International audience 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. |
author2 |
Génie Enzymatique et Cellulaire (GEC) Université de Technologie de Compiègne (UTC)-Centre National de la Recherche Scientifique (CNRS) Laboratoire réactivité et chimie des solides - UMR CNRS 7314 (LRCS) Réseau sur le stockage électrochimique de l'énergie (RS2E) Université de Nantes (UN)-Aix Marseille Université (AMU)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Collège de France (CdF (institution))-Université de Picardie Jules Verne (UPJV)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP) Université Paris Sciences et Lettres (PSL)-Université Paris Sciences et Lettres (PSL)-Université de Pau et des Pays de l'Adour (UPPA)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Université de Montpellier (UM)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP) Université de Toulouse (UT)-Université de Toulouse (UT)-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP ) Université Grenoble Alpes (UGA)-Université Grenoble Alpes (UGA)-Université de Nantes (UN)-Aix Marseille Université (AMU)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Collège de France (CdF (institution))-Université de Picardie Jules Verne (UPJV)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP) Université Grenoble Alpes (UGA)-Université Grenoble Alpes (UGA)-Advanced Lithium Energy Storage Systems - ALISTORE-ERI (ALISTORE-ERI) Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Réseau sur le stockage électrochimique de l'énergie (RS2E) Aix Marseille Université (AMU)-Université Toulouse III - Paul Sabatier (UT3) Université de Toulouse (UT)-Université de Toulouse (UT)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Collège de France (CdF (institution))-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP) Université Paris Sciences et Lettres (PSL)-Université Paris Sciences et Lettres (PSL)-Université de Pau et des Pays de l'Adour (UPPA)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP) Université de Toulouse (UT)-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP ) Université Grenoble Alpes (UGA)-Université Grenoble Alpes (UGA)-Nantes Université (Nantes Univ)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM) Université de Montpellier (UM)-Université Toulouse III - Paul Sabatier (UT3) Université de Toulouse (UT)-Nantes Université (Nantes Univ)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM) Université de Montpellier (UM) Centre de Recherche sur les Matériaux Renouvelables Université Laval Québec (ULaval) |
format |
Article in Journal/Newspaper |
author |
Hulin, L. Husson, E. Bonnet, Jean-Pierre Stevanovic, T. Sarazin, C. |
author_facet |
Hulin, L. Husson, E. Bonnet, Jean-Pierre Stevanovic, T. Sarazin, C. |
author_sort |
Hulin, L. |
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 |
HAL CCSD |
publishDate |
2015 |
url |
https://hal.science/hal-01344626 https://hal.science/hal-01344626/document https://hal.science/hal-01344626/file/molecules-20-16334.pdf https://doi.org/10.3390/molecules200916334 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
ISSN: 1420-3049 Molecules https://hal.science/hal-01344626 Molecules, 2015, 20 (9), pp.16334-16353. ⟨10.3390/molecules200916334⟩ |
op_relation |
info:eu-repo/semantics/altIdentifier/doi/10.3390/molecules200916334 hal-01344626 https://hal.science/hal-01344626 https://hal.science/hal-01344626/document https://hal.science/hal-01344626/file/molecules-20-16334.pdf doi:10.3390/molecules200916334 PUBMEDCENTRAL: PMC6332217 |
op_rights |
http://creativecommons.org/licenses/by/ info:eu-repo/semantics/OpenAccess |
op_doi |
https://doi.org/10.3390/molecules200916334 |
container_title |
Molecules |
container_volume |
20 |
container_issue |
9 |
container_start_page |
16334 |
op_container_end_page |
16353 |
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1800755869043916800 |
spelling |
ftunivpicardie:oai:HAL:hal-01344626v1 2024-06-02T07:56:25+00:00 Enzymatic transesterification of kraft lignin with long acyl chains in ionic liquids Hulin, L. Husson, E. Bonnet, Jean-Pierre Stevanovic, T. Sarazin, C. Génie Enzymatique et Cellulaire (GEC) Université de Technologie de Compiègne (UTC)-Centre National de la Recherche Scientifique (CNRS) Laboratoire réactivité et chimie des solides - UMR CNRS 7314 (LRCS) Réseau sur le stockage électrochimique de l'énergie (RS2E) Université de Nantes (UN)-Aix Marseille Université (AMU)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Collège de France (CdF (institution))-Université de Picardie Jules Verne (UPJV)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP) Université Paris Sciences et Lettres (PSL)-Université Paris Sciences et Lettres (PSL)-Université de Pau et des Pays de l'Adour (UPPA)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Université de Montpellier (UM)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP) Université de Toulouse (UT)-Université de Toulouse (UT)-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP ) Université Grenoble Alpes (UGA)-Université Grenoble Alpes (UGA)-Université de Nantes (UN)-Aix Marseille Université (AMU)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Collège de France (CdF (institution))-Université de Picardie Jules Verne (UPJV)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP) Université Grenoble Alpes (UGA)-Université Grenoble Alpes (UGA)-Advanced Lithium Energy Storage Systems - ALISTORE-ERI (ALISTORE-ERI) Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Réseau sur le stockage électrochimique de l'énergie (RS2E) Aix Marseille Université (AMU)-Université Toulouse III - Paul Sabatier (UT3) Université de Toulouse (UT)-Université de Toulouse (UT)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Collège de France (CdF (institution))-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP) Université Paris Sciences et Lettres (PSL)-Université Paris Sciences et Lettres (PSL)-Université de Pau et des Pays de l'Adour (UPPA)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP) Université de Toulouse (UT)-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP ) Université Grenoble Alpes (UGA)-Université Grenoble Alpes (UGA)-Nantes Université (Nantes Univ)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM) Université de Montpellier (UM)-Université Toulouse III - Paul Sabatier (UT3) Université de Toulouse (UT)-Nantes Université (Nantes Univ)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM) Université de Montpellier (UM) Centre de Recherche sur les Matériaux Renouvelables Université Laval Québec (ULaval) 2015 https://hal.science/hal-01344626 https://hal.science/hal-01344626/document https://hal.science/hal-01344626/file/molecules-20-16334.pdf https://doi.org/10.3390/molecules200916334 en eng HAL CCSD MDPI info:eu-repo/semantics/altIdentifier/doi/10.3390/molecules200916334 hal-01344626 https://hal.science/hal-01344626 https://hal.science/hal-01344626/document https://hal.science/hal-01344626/file/molecules-20-16334.pdf doi:10.3390/molecules200916334 PUBMEDCENTRAL: PMC6332217 http://creativecommons.org/licenses/by/ info:eu-repo/semantics/OpenAccess ISSN: 1420-3049 Molecules https://hal.science/hal-01344626 Molecules, 2015, 20 (9), pp.16334-16353. ⟨10.3390/molecules200916334⟩ lignin enzymatic esterification lipase ionic liquids [SDV]Life Sciences [q-bio] [CHIM]Chemical Sciences info:eu-repo/semantics/article Journal articles 2015 ftunivpicardie https://doi.org/10.3390/molecules200916334 2024-05-07T02:39:22Z International audience 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. Article in Journal/Newspaper Antarc* Antarctica Université de Picardie Jules Verne Molecules 20 9 16334 16353 |