Effect of methoxy substituents on wet peroxide oxidation of lignin and lignin model compounds: understanding the pathway to c4 dicarboxylic acids

Detalhes bibliográficos
Autor(a) principal: Rodrigues, Alírio
Data de Publicação: 2018
Outros Autores: Vega-Aguilar, Carlos, Barreiro, M.F.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10198/24380
Resumo: Lignin depolymerization through peroxide oxidation produces dicarboxylic acids (DCA), especially C4-DCA, like succinic acid. In this work, the effect of methoxy substituents on C4-DCA production using peroxide oxidation of lignin model compounds (p-hydroxybenzoic acid, vanillic acid, and syringic acid) and hardwood and softwood lignin samples was studied. It was concluded that methoxy substituents increased the reactivity toward peroxide oxidation. The succinic acid yield was higher for the model compounds with fewer methoxy groups, achieving 5.8 wt % of succinic acid for p-hydroxybenzoic acid. For Eucalyptus globulus kraft lignin (hardwood lignin with guaiacyl and syringyl units), an increased reactivity was verified, and more succinic acid (3.5 wt %) was produced in a shorter time, comparatively with Indulin AT lignin (softwood lignin, with only guaiacyl units), which produced 2.7 wt %. This evidence suggests that E. globulus kraft lignin might be a better raw material than Indulin AT for succinic acid production by peroxide oxidation.
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spelling Effect of methoxy substituents on wet peroxide oxidation of lignin and lignin model compounds: understanding the pathway to c4 dicarboxylic acidsLignin depolymerization through peroxide oxidation produces dicarboxylic acids (DCA), especially C4-DCA, like succinic acid. In this work, the effect of methoxy substituents on C4-DCA production using peroxide oxidation of lignin model compounds (p-hydroxybenzoic acid, vanillic acid, and syringic acid) and hardwood and softwood lignin samples was studied. It was concluded that methoxy substituents increased the reactivity toward peroxide oxidation. The succinic acid yield was higher for the model compounds with fewer methoxy groups, achieving 5.8 wt % of succinic acid for p-hydroxybenzoic acid. For Eucalyptus globulus kraft lignin (hardwood lignin with guaiacyl and syringyl units), an increased reactivity was verified, and more succinic acid (3.5 wt %) was produced in a shorter time, comparatively with Indulin AT lignin (softwood lignin, with only guaiacyl units), which produced 2.7 wt %. This evidence suggests that E. globulus kraft lignin might be a better raw material than Indulin AT for succinic acid production by peroxide oxidation.This work was financially supported by Base Funding − UIDB/50020/2020 of the Associate Laboratory LSRE-LCM − funded by national funds through FCT/MCTES (PIDDAC); Base Funding−UIDB/00690/2020 of CIMO, Centro de Investigação de Montanha−funded by national funds through FCT/MCTES (PIDDAC); COST Action LignoCOST (CA17128). C.A.V.-A. thanks the Costa Rican Science, Technology and Telecommunications Ministry for the Ph.D. Scholarship MICITT-PINN-CON-2-1-4-17-1-002.Biblioteca Digital do IPBRodrigues, AlírioVega-Aguilar, CarlosBarreiro, M.F.2018-01-19T10:00:00Z20212021-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10198/24380engRodrigues, Alírio E.; Vega-Aguilar, Carlos A.; Filomena Barreiro, M. (2021). Effect of methoxy substituents on wet peroxide oxidation of lignin and lignin model compounds: Understanding the pathway to c4 dicarboxylic acids. Industrial and Engineering Chemistry Research. ISSN 0888-5885. 60:9, p. 3543-35530888-588510.1021/acs.iecr.0c05085info: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:RCAAP2023-11-21T10:54:32Zoai:bibliotecadigital.ipb.pt:10198/24380Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T23:15:13.488671Repositório 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 Effect of methoxy substituents on wet peroxide oxidation of lignin and lignin model compounds: understanding the pathway to c4 dicarboxylic acids
title Effect of methoxy substituents on wet peroxide oxidation of lignin and lignin model compounds: understanding the pathway to c4 dicarboxylic acids
spellingShingle Effect of methoxy substituents on wet peroxide oxidation of lignin and lignin model compounds: understanding the pathway to c4 dicarboxylic acids
Rodrigues, Alírio
title_short Effect of methoxy substituents on wet peroxide oxidation of lignin and lignin model compounds: understanding the pathway to c4 dicarboxylic acids
title_full Effect of methoxy substituents on wet peroxide oxidation of lignin and lignin model compounds: understanding the pathway to c4 dicarboxylic acids
title_fullStr Effect of methoxy substituents on wet peroxide oxidation of lignin and lignin model compounds: understanding the pathway to c4 dicarboxylic acids
title_full_unstemmed Effect of methoxy substituents on wet peroxide oxidation of lignin and lignin model compounds: understanding the pathway to c4 dicarboxylic acids
title_sort Effect of methoxy substituents on wet peroxide oxidation of lignin and lignin model compounds: understanding the pathway to c4 dicarboxylic acids
author Rodrigues, Alírio
author_facet Rodrigues, Alírio
Vega-Aguilar, Carlos
Barreiro, M.F.
author_role author
author2 Vega-Aguilar, Carlos
Barreiro, M.F.
author2_role author
author
dc.contributor.none.fl_str_mv Biblioteca Digital do IPB
dc.contributor.author.fl_str_mv Rodrigues, Alírio
Vega-Aguilar, Carlos
Barreiro, M.F.
description Lignin depolymerization through peroxide oxidation produces dicarboxylic acids (DCA), especially C4-DCA, like succinic acid. In this work, the effect of methoxy substituents on C4-DCA production using peroxide oxidation of lignin model compounds (p-hydroxybenzoic acid, vanillic acid, and syringic acid) and hardwood and softwood lignin samples was studied. It was concluded that methoxy substituents increased the reactivity toward peroxide oxidation. The succinic acid yield was higher for the model compounds with fewer methoxy groups, achieving 5.8 wt % of succinic acid for p-hydroxybenzoic acid. For Eucalyptus globulus kraft lignin (hardwood lignin with guaiacyl and syringyl units), an increased reactivity was verified, and more succinic acid (3.5 wt %) was produced in a shorter time, comparatively with Indulin AT lignin (softwood lignin, with only guaiacyl units), which produced 2.7 wt %. This evidence suggests that E. globulus kraft lignin might be a better raw material than Indulin AT for succinic acid production by peroxide oxidation.
publishDate 2018
dc.date.none.fl_str_mv 2018-01-19T10:00:00Z
2021
2021-01-01T00:00:00Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
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status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/10198/24380
url http://hdl.handle.net/10198/24380
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Rodrigues, Alírio E.; Vega-Aguilar, Carlos A.; Filomena Barreiro, M. (2021). Effect of methoxy substituents on wet peroxide oxidation of lignin and lignin model compounds: Understanding the pathway to c4 dicarboxylic acids. Industrial and Engineering Chemistry Research. ISSN 0888-5885. 60:9, p. 3543-3553
0888-5885
10.1021/acs.iecr.0c05085
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