Regioselective Acylation of Levoglucosan Catalyzed by Candida Antarctica (CaLB) Lipase Immobilized on Epoxy Resin
International audience Every year, a large amount of residual agroindustrial waste has been generated and only around 10% is in fact reused. The development of new strategies for biomass valorization is important to add value to these commodities, since biomass is an excellent alternative feedstock...
Published in: | Sustainability |
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Format: | Article in Journal/Newspaper |
Language: | English |
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HAL CCSD
2019
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Online Access: | https://hal.univ-lille.fr/hal-03025754 https://hal.univ-lille.fr/hal-03025754/document https://hal.univ-lille.fr/hal-03025754/file/sustainability-11-06044-v2.pdf https://doi.org/10.3390/su11216044 |
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ftccsdartic:oai:HAL:hal-03025754v1 2023-05-15T13:49:24+02:00 Regioselective Acylation of Levoglucosan Catalyzed by Candida Antarctica (CaLB) Lipase Immobilized on Epoxy Resin Avelar do Nascimento, Marcelo Ester Gotardo, Larissa Miguez Bastos, Eduardo C. L. Almeida, Fabio A. C. Leão, Raquel O. M. A. de Souza, Rodrigo Wojcieszak, Robert Itabaiana, Ivaldo Unité de Catalyse et Chimie du Solide - UMR 8181 (UCCS) Centrale Lille Institut (CLIL)-Université d'Artois (UA)-Centrale Lille-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Lille 2019-10-31 https://hal.univ-lille.fr/hal-03025754 https://hal.univ-lille.fr/hal-03025754/document https://hal.univ-lille.fr/hal-03025754/file/sustainability-11-06044-v2.pdf https://doi.org/10.3390/su11216044 en eng HAL CCSD info:eu-repo/semantics/altIdentifier/doi/10.3390/su11216044 hal-03025754 https://hal.univ-lille.fr/hal-03025754 https://hal.univ-lille.fr/hal-03025754/document https://hal.univ-lille.fr/hal-03025754/file/sustainability-11-06044-v2.pdf doi:10.3390/su11216044 http://creativecommons.org/licenses/by/ info:eu-repo/semantics/OpenAccess Sustainability https://hal.univ-lille.fr/hal-03025754 Sustainability, 2019, Sustainability, 11 (21), pp.6044. ⟨10.3390/su11216044⟩ [CHIM.CATA]Chemical Sciences/Catalysis info:eu-repo/semantics/article Journal articles 2019 ftccsdartic https://doi.org/10.3390/su11216044 2021-12-19T00:43:52Z International audience Every year, a large amount of residual agroindustrial waste has been generated and only around 10% is in fact reused. The development of new strategies for biomass valorization is important to add value to these commodities, since biomass is an excellent alternative feedstock to obtain chemicals of interest from renewable resources. The major compound of pyrolytic treatment of lignocellulosic biomass is levoglucosan (1,6-anhydroglucopyranose), an anhydro-sugar that can be transformed into glucose and is greatly valued in the most diverse industrial sectors as a surfactant, emulsifier, or even a lubricant. In this work, levoglucosan was acylated by lipase-catalyzed transesterification in acetonitrile with great conversions and selectivities with different acyl donors such as ethyl esters of lauric, palmitic, stearic, and oleic acids prepared in situ in an integrated strategy mediated by commercial lipases Novozym435 (N435), PSIM, and the home-made biocatalyst CaLB_epoxy. As a result, all biocatalyst generated mostly monoesters, with N435 being more selective to produce lauric esters (99% at 50°C) and PSIM to produce oleic esters (97% at 55 °C) while CaLB_epoxy was more selective to produce oleic esters of levoglucosan (83% at 55°C). This is the first report in the literature on the production of high selectivity levoglucosan esters. Article in Journal/Newspaper Antarc* Antarctica Archive ouverte HAL (Hyper Article en Ligne, CCSD - Centre pour la Communication Scientifique Directe) Sustainability 11 21 6044 |
institution |
Open Polar |
collection |
Archive ouverte HAL (Hyper Article en Ligne, CCSD - Centre pour la Communication Scientifique Directe) |
op_collection_id |
ftccsdartic |
language |
English |
topic |
[CHIM.CATA]Chemical Sciences/Catalysis |
spellingShingle |
[CHIM.CATA]Chemical Sciences/Catalysis Avelar do Nascimento, Marcelo Ester Gotardo, Larissa Miguez Bastos, Eduardo C. L. Almeida, Fabio A. C. Leão, Raquel O. M. A. de Souza, Rodrigo Wojcieszak, Robert Itabaiana, Ivaldo Regioselective Acylation of Levoglucosan Catalyzed by Candida Antarctica (CaLB) Lipase Immobilized on Epoxy Resin |
topic_facet |
[CHIM.CATA]Chemical Sciences/Catalysis |
description |
International audience Every year, a large amount of residual agroindustrial waste has been generated and only around 10% is in fact reused. The development of new strategies for biomass valorization is important to add value to these commodities, since biomass is an excellent alternative feedstock to obtain chemicals of interest from renewable resources. The major compound of pyrolytic treatment of lignocellulosic biomass is levoglucosan (1,6-anhydroglucopyranose), an anhydro-sugar that can be transformed into glucose and is greatly valued in the most diverse industrial sectors as a surfactant, emulsifier, or even a lubricant. In this work, levoglucosan was acylated by lipase-catalyzed transesterification in acetonitrile with great conversions and selectivities with different acyl donors such as ethyl esters of lauric, palmitic, stearic, and oleic acids prepared in situ in an integrated strategy mediated by commercial lipases Novozym435 (N435), PSIM, and the home-made biocatalyst CaLB_epoxy. As a result, all biocatalyst generated mostly monoesters, with N435 being more selective to produce lauric esters (99% at 50°C) and PSIM to produce oleic esters (97% at 55 °C) while CaLB_epoxy was more selective to produce oleic esters of levoglucosan (83% at 55°C). This is the first report in the literature on the production of high selectivity levoglucosan esters. |
author2 |
Unité de Catalyse et Chimie du Solide - UMR 8181 (UCCS) Centrale Lille Institut (CLIL)-Université d'Artois (UA)-Centrale Lille-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Lille |
format |
Article in Journal/Newspaper |
author |
Avelar do Nascimento, Marcelo Ester Gotardo, Larissa Miguez Bastos, Eduardo C. L. Almeida, Fabio A. C. Leão, Raquel O. M. A. de Souza, Rodrigo Wojcieszak, Robert Itabaiana, Ivaldo |
author_facet |
Avelar do Nascimento, Marcelo Ester Gotardo, Larissa Miguez Bastos, Eduardo C. L. Almeida, Fabio A. C. Leão, Raquel O. M. A. de Souza, Rodrigo Wojcieszak, Robert Itabaiana, Ivaldo |
author_sort |
Avelar do Nascimento, Marcelo |
title |
Regioselective Acylation of Levoglucosan Catalyzed by Candida Antarctica (CaLB) Lipase Immobilized on Epoxy Resin |
title_short |
Regioselective Acylation of Levoglucosan Catalyzed by Candida Antarctica (CaLB) Lipase Immobilized on Epoxy Resin |
title_full |
Regioselective Acylation of Levoglucosan Catalyzed by Candida Antarctica (CaLB) Lipase Immobilized on Epoxy Resin |
title_fullStr |
Regioselective Acylation of Levoglucosan Catalyzed by Candida Antarctica (CaLB) Lipase Immobilized on Epoxy Resin |
title_full_unstemmed |
Regioselective Acylation of Levoglucosan Catalyzed by Candida Antarctica (CaLB) Lipase Immobilized on Epoxy Resin |
title_sort |
regioselective acylation of levoglucosan catalyzed by candida antarctica (calb) lipase immobilized on epoxy resin |
publisher |
HAL CCSD |
publishDate |
2019 |
url |
https://hal.univ-lille.fr/hal-03025754 https://hal.univ-lille.fr/hal-03025754/document https://hal.univ-lille.fr/hal-03025754/file/sustainability-11-06044-v2.pdf https://doi.org/10.3390/su11216044 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Sustainability https://hal.univ-lille.fr/hal-03025754 Sustainability, 2019, Sustainability, 11 (21), pp.6044. ⟨10.3390/su11216044⟩ |
op_relation |
info:eu-repo/semantics/altIdentifier/doi/10.3390/su11216044 hal-03025754 https://hal.univ-lille.fr/hal-03025754 https://hal.univ-lille.fr/hal-03025754/document https://hal.univ-lille.fr/hal-03025754/file/sustainability-11-06044-v2.pdf doi:10.3390/su11216044 |
op_rights |
http://creativecommons.org/licenses/by/ info:eu-repo/semantics/OpenAccess |
op_doi |
https://doi.org/10.3390/su11216044 |
container_title |
Sustainability |
container_volume |
11 |
container_issue |
21 |
container_start_page |
6044 |
_version_ |
1766251304727871488 |