Unveiling the dual role of the cholinium hexanoate ionic liquid as solvent and catalyst in suberin depolymerisation
Autor(a) principal: | |
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Data de Publicação: | 2014 |
Outros Autores: | , , , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10773/19863 |
Resumo: | Disruption of the three-dimensional network of suberin in cork by cholinium hexanoate leads to its efficient and selective isolation. The reaction mechanism, which likely involves selective cleavage of some inter-monomeric bonds in suberin, was still unanswered. To address this question, the role of the ionic liquid during suberin depolymerisation and during cleavage of standard compounds carrying key chemical functionalities was herein investigated. A clear demonstration that the ionic liquid catalyses the hydrolysis of acylglycerol ester bonds was attained herein, both experimentally and computationally (DFT calculations). This behaviour is related to cholinium hexanoate capacity to activate the nucleophilic attack of water. The data showed also that the most favourable reaction is the hydrolysis of acylglycerol ester bonds, with the C2 position reporting the faster kinetics, whilst most of the linear aliphatic esters remained intact. The study emphasises that the ionic liquid plays the dual role of solvent and catalyst and leads to suberin efficient extraction through a mild depolymerisation. It is also one of the few reports of ionic liquids as efficient catalysts in the hydrolysis of esters. |
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Unveiling the dual role of the cholinium hexanoate ionic liquid as solvent and catalyst in suberin depolymerisationBIRCH OUTER BARKCORK SUBERINPOTATO-TUBERSTRUCTURAL-CHARACTERIZATIONQUERCUS-SUBERFERULIC ACIDCELL-WALLCUTINPOLYESTERBIOSYNTHESISDisruption of the three-dimensional network of suberin in cork by cholinium hexanoate leads to its efficient and selective isolation. The reaction mechanism, which likely involves selective cleavage of some inter-monomeric bonds in suberin, was still unanswered. To address this question, the role of the ionic liquid during suberin depolymerisation and during cleavage of standard compounds carrying key chemical functionalities was herein investigated. A clear demonstration that the ionic liquid catalyses the hydrolysis of acylglycerol ester bonds was attained herein, both experimentally and computationally (DFT calculations). This behaviour is related to cholinium hexanoate capacity to activate the nucleophilic attack of water. The data showed also that the most favourable reaction is the hydrolysis of acylglycerol ester bonds, with the C2 position reporting the faster kinetics, whilst most of the linear aliphatic esters remained intact. The study emphasises that the ionic liquid plays the dual role of solvent and catalyst and leads to suberin efficient extraction through a mild depolymerisation. It is also one of the few reports of ionic liquids as efficient catalysts in the hydrolysis of esters.ROYAL SOC CHEMISTRY2017-12-07T19:27:25Z2014-01-01T00:00:00Z2014info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10773/19863eng2046-206910.1039/c3ra45910aFerreira, RuiGarcia, HelgaSousa, Andreia F.Guerreiro, MarinaDuarte, Filipe J. S.Freire, Carmen S. R.Calhorda, Maria JoseSilvestre, Armando J. D.Kunz, WernerRebelo, Luis Paulo N.Pereira, Cristina Silvainfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-02-22T11:38:45Zoai:ria.ua.pt:10773/19863Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T02:54:35.697028Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
dc.title.none.fl_str_mv |
Unveiling the dual role of the cholinium hexanoate ionic liquid as solvent and catalyst in suberin depolymerisation |
title |
Unveiling the dual role of the cholinium hexanoate ionic liquid as solvent and catalyst in suberin depolymerisation |
spellingShingle |
Unveiling the dual role of the cholinium hexanoate ionic liquid as solvent and catalyst in suberin depolymerisation Ferreira, Rui BIRCH OUTER BARK CORK SUBERIN POTATO-TUBER STRUCTURAL-CHARACTERIZATION QUERCUS-SUBER FERULIC ACID CELL-WALL CUTIN POLYESTER BIOSYNTHESIS |
title_short |
Unveiling the dual role of the cholinium hexanoate ionic liquid as solvent and catalyst in suberin depolymerisation |
title_full |
Unveiling the dual role of the cholinium hexanoate ionic liquid as solvent and catalyst in suberin depolymerisation |
title_fullStr |
Unveiling the dual role of the cholinium hexanoate ionic liquid as solvent and catalyst in suberin depolymerisation |
title_full_unstemmed |
Unveiling the dual role of the cholinium hexanoate ionic liquid as solvent and catalyst in suberin depolymerisation |
title_sort |
Unveiling the dual role of the cholinium hexanoate ionic liquid as solvent and catalyst in suberin depolymerisation |
author |
Ferreira, Rui |
author_facet |
Ferreira, Rui Garcia, Helga Sousa, Andreia F. Guerreiro, Marina Duarte, Filipe J. S. Freire, Carmen S. R. Calhorda, Maria Jose Silvestre, Armando J. D. Kunz, Werner Rebelo, Luis Paulo N. Pereira, Cristina Silva |
author_role |
author |
author2 |
Garcia, Helga Sousa, Andreia F. Guerreiro, Marina Duarte, Filipe J. S. Freire, Carmen S. R. Calhorda, Maria Jose Silvestre, Armando J. D. Kunz, Werner Rebelo, Luis Paulo N. Pereira, Cristina Silva |
author2_role |
author author author author author author author author author author |
dc.contributor.author.fl_str_mv |
Ferreira, Rui Garcia, Helga Sousa, Andreia F. Guerreiro, Marina Duarte, Filipe J. S. Freire, Carmen S. R. Calhorda, Maria Jose Silvestre, Armando J. D. Kunz, Werner Rebelo, Luis Paulo N. Pereira, Cristina Silva |
dc.subject.por.fl_str_mv |
BIRCH OUTER BARK CORK SUBERIN POTATO-TUBER STRUCTURAL-CHARACTERIZATION QUERCUS-SUBER FERULIC ACID CELL-WALL CUTIN POLYESTER BIOSYNTHESIS |
topic |
BIRCH OUTER BARK CORK SUBERIN POTATO-TUBER STRUCTURAL-CHARACTERIZATION QUERCUS-SUBER FERULIC ACID CELL-WALL CUTIN POLYESTER BIOSYNTHESIS |
description |
Disruption of the three-dimensional network of suberin in cork by cholinium hexanoate leads to its efficient and selective isolation. The reaction mechanism, which likely involves selective cleavage of some inter-monomeric bonds in suberin, was still unanswered. To address this question, the role of the ionic liquid during suberin depolymerisation and during cleavage of standard compounds carrying key chemical functionalities was herein investigated. A clear demonstration that the ionic liquid catalyses the hydrolysis of acylglycerol ester bonds was attained herein, both experimentally and computationally (DFT calculations). This behaviour is related to cholinium hexanoate capacity to activate the nucleophilic attack of water. The data showed also that the most favourable reaction is the hydrolysis of acylglycerol ester bonds, with the C2 position reporting the faster kinetics, whilst most of the linear aliphatic esters remained intact. The study emphasises that the ionic liquid plays the dual role of solvent and catalyst and leads to suberin efficient extraction through a mild depolymerisation. It is also one of the few reports of ionic liquids as efficient catalysts in the hydrolysis of esters. |
publishDate |
2014 |
dc.date.none.fl_str_mv |
2014-01-01T00:00:00Z 2014 2017-12-07T19:27:25Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/10773/19863 |
url |
http://hdl.handle.net/10773/19863 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
2046-2069 10.1039/c3ra45910a |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
ROYAL SOC CHEMISTRY |
publisher.none.fl_str_mv |
ROYAL SOC CHEMISTRY |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
instname_str |
Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
instacron_str |
RCAAP |
institution |
RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
collection |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
repository.name.fl_str_mv |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
repository.mail.fl_str_mv |
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1799137598647566336 |