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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doaj-662e48ba63a14b49ab44de4a8b846e862020-11-25T00:30:58ZengMDPI AGMolecules1420-30492015-09-01209163341635310.3390/molecules200916334molecules200916334Enzymatic Transesterification of Kraft Lignin with Long Acyl Chains in Ionic LiquidsLise Hulin0Eric Husson1Jean-Pierre Bonnet2Tatjana Stevanovic3Catherine Sarazin4Unité de Génie Enzymatique et Cellulaire, FRE CNRS 3580, Université de Picardie Jules Verne, 33 Rue Saint-Leu, 80039 Amiens, FranceUnité de Génie Enzymatique et Cellulaire, FRE CNRS 3580, Université de Picardie Jules Verne, 33 Rue Saint-Leu, 80039 Amiens, FranceLaboratoire de Réactivité et Chimie des Solides, UMR CNRS 7314, Université de Picardie Jules Verne, 33 Rue Saint-Leu, 80039 Amiens, FranceSciences du Bois et de la Forêt, Centre de Recherche sur les Matériaux Renouvelables, Université Laval, 2425 Rue de la Terrasse, Québec, QC G1V 0A6, CanadaUnité de Génie Enzymatique et Cellulaire, FRE CNRS 3580, Université de Picardie Jules Verne, 33 Rue Saint-Leu, 80039 Amiens, FranceValorization 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.http://www.mdpi.com/1420-3049/20/9/16334ligninenzymatic esterificationlipaseionic liquids |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Lise Hulin Eric Husson Jean-Pierre Bonnet Tatjana Stevanovic Catherine Sarazin |
spellingShingle |
Lise Hulin Eric Husson Jean-Pierre Bonnet Tatjana Stevanovic Catherine Sarazin Enzymatic Transesterification of Kraft Lignin with Long Acyl Chains in Ionic Liquids Molecules lignin enzymatic esterification lipase ionic liquids |
author_facet |
Lise Hulin Eric Husson Jean-Pierre Bonnet Tatjana Stevanovic Catherine Sarazin |
author_sort |
Lise Hulin |
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 AG |
series |
Molecules |
issn |
1420-3049 |
publishDate |
2015-09-01 |
description |
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. |
topic |
lignin enzymatic esterification lipase ionic liquids |
url |
http://www.mdpi.com/1420-3049/20/9/16334 |
work_keys_str_mv |
AT lisehulin enzymatictransesterificationofkraftligninwithlongacylchainsinionicliquids AT erichusson enzymatictransesterificationofkraftligninwithlongacylchainsinionicliquids AT jeanpierrebonnet enzymatictransesterificationofkraftligninwithlongacylchainsinionicliquids AT tatjanastevanovic enzymatictransesterificationofkraftligninwithlongacylchainsinionicliquids AT catherinesarazin enzymatictransesterificationofkraftligninwithlongacylchainsinionicliquids |
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1725324657378197504 |