Cationization of eucalyptus kraft lignoboost lignin: preparation, properties, and potential applications

Detalhes bibliográficos
Autor(a) principal: Pinto, Patrícia I.F.
Data de Publicação: 2022
Outros Autores: Magina, Sandra, Budjav, Enkhjargal, Pinto, Paula C.R., Liebner, Falk, Evtuguin, Dmitry
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10773/35936
Resumo: Current changes toward a more biobased economy have recently created tremendous renewed interest in using lignin as a valuable source for chemicals and materials. Here, we present a facile cationization approach aiming to impart kraft lignin water-solubility, with similar good features as lignosulfonates. Eucalyptus globulus kraft lignin obtained from a paper mill black liquor by applying the LignoBoost process was used as the substrate. Its reaction with 3-chloro-2-hydroxypropyl-trimethylammonium chloride (CHPTAC) in an aqueous alkaline medium was studied to assess the impact of different reaction conditions (temperature, time, educt concentration, molar CHPTAC-to-lignin ratio) on the degree of cationization. It has been shown that at pH 13, 10 wt % lignin content, 70 °C, and 3 h reaction time, a CHPTAC-to-lignin minimum molar ratio of 1.3 is required to obtain fully water-soluble products. Elemental analysis (4.2% N), size-exclusion chromatography (M w 2180 Da), and quantitative 13C NMR spectroscopy of the product obtained at this limit reactant concentration suggest introduction of 1.2 quaternary ammonium groups per C9 unit and substitution of 75% of the initially available phenolic OH groups. The possible contribution of benzylic hydroxyls to the introduction of quaternary ammonium moieties through a quinone methide mechanism has been proposed. Since both molecular characteristics and degree of substitution, and hence solubility or count of surface charge, of colloidal particles can be adjusted within a wide range, cationic kraft lignins are promising materials for a wide range of applications, as exemplarily demonstrated for flocculation of anionic dyes.
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spelling Cationization of eucalyptus kraft lignoboost lignin: preparation, properties, and potential applicationsCurrent changes toward a more biobased economy have recently created tremendous renewed interest in using lignin as a valuable source for chemicals and materials. Here, we present a facile cationization approach aiming to impart kraft lignin water-solubility, with similar good features as lignosulfonates. Eucalyptus globulus kraft lignin obtained from a paper mill black liquor by applying the LignoBoost process was used as the substrate. Its reaction with 3-chloro-2-hydroxypropyl-trimethylammonium chloride (CHPTAC) in an aqueous alkaline medium was studied to assess the impact of different reaction conditions (temperature, time, educt concentration, molar CHPTAC-to-lignin ratio) on the degree of cationization. It has been shown that at pH 13, 10 wt % lignin content, 70 °C, and 3 h reaction time, a CHPTAC-to-lignin minimum molar ratio of 1.3 is required to obtain fully water-soluble products. Elemental analysis (4.2% N), size-exclusion chromatography (M w 2180 Da), and quantitative 13C NMR spectroscopy of the product obtained at this limit reactant concentration suggest introduction of 1.2 quaternary ammonium groups per C9 unit and substitution of 75% of the initially available phenolic OH groups. The possible contribution of benzylic hydroxyls to the introduction of quaternary ammonium moieties through a quinone methide mechanism has been proposed. Since both molecular characteristics and degree of substitution, and hence solubility or count of surface charge, of colloidal particles can be adjusted within a wide range, cationic kraft lignins are promising materials for a wide range of applications, as exemplarily demonstrated for flocculation of anionic dyes.American Chemical Society2023-01-20T15:59:42Z2022-03-16T00:00:00Z2022-03-16info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10773/35936eng0888-588510.1021/acs.iecr.1c04899Pinto, Patrícia I.F.Magina, SandraBudjav, EnkhjargalPinto, Paula C.R.Liebner, FalkEvtuguin, Dmitryinfo: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:RCAAP2024-02-22T12:09:23Zoai:ria.ua.pt:10773/35936Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:06:55.855289Repositório 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 Cationization of eucalyptus kraft lignoboost lignin: preparation, properties, and potential applications
title Cationization of eucalyptus kraft lignoboost lignin: preparation, properties, and potential applications
spellingShingle Cationization of eucalyptus kraft lignoboost lignin: preparation, properties, and potential applications
Pinto, Patrícia I.F.
title_short Cationization of eucalyptus kraft lignoboost lignin: preparation, properties, and potential applications
title_full Cationization of eucalyptus kraft lignoboost lignin: preparation, properties, and potential applications
title_fullStr Cationization of eucalyptus kraft lignoboost lignin: preparation, properties, and potential applications
title_full_unstemmed Cationization of eucalyptus kraft lignoboost lignin: preparation, properties, and potential applications
title_sort Cationization of eucalyptus kraft lignoboost lignin: preparation, properties, and potential applications
author Pinto, Patrícia I.F.
author_facet Pinto, Patrícia I.F.
Magina, Sandra
Budjav, Enkhjargal
Pinto, Paula C.R.
Liebner, Falk
Evtuguin, Dmitry
author_role author
author2 Magina, Sandra
Budjav, Enkhjargal
Pinto, Paula C.R.
Liebner, Falk
Evtuguin, Dmitry
author2_role author
author
author
author
author
dc.contributor.author.fl_str_mv Pinto, Patrícia I.F.
Magina, Sandra
Budjav, Enkhjargal
Pinto, Paula C.R.
Liebner, Falk
Evtuguin, Dmitry
description Current changes toward a more biobased economy have recently created tremendous renewed interest in using lignin as a valuable source for chemicals and materials. Here, we present a facile cationization approach aiming to impart kraft lignin water-solubility, with similar good features as lignosulfonates. Eucalyptus globulus kraft lignin obtained from a paper mill black liquor by applying the LignoBoost process was used as the substrate. Its reaction with 3-chloro-2-hydroxypropyl-trimethylammonium chloride (CHPTAC) in an aqueous alkaline medium was studied to assess the impact of different reaction conditions (temperature, time, educt concentration, molar CHPTAC-to-lignin ratio) on the degree of cationization. It has been shown that at pH 13, 10 wt % lignin content, 70 °C, and 3 h reaction time, a CHPTAC-to-lignin minimum molar ratio of 1.3 is required to obtain fully water-soluble products. Elemental analysis (4.2% N), size-exclusion chromatography (M w 2180 Da), and quantitative 13C NMR spectroscopy of the product obtained at this limit reactant concentration suggest introduction of 1.2 quaternary ammonium groups per C9 unit and substitution of 75% of the initially available phenolic OH groups. The possible contribution of benzylic hydroxyls to the introduction of quaternary ammonium moieties through a quinone methide mechanism has been proposed. Since both molecular characteristics and degree of substitution, and hence solubility or count of surface charge, of colloidal particles can be adjusted within a wide range, cationic kraft lignins are promising materials for a wide range of applications, as exemplarily demonstrated for flocculation of anionic dyes.
publishDate 2022
dc.date.none.fl_str_mv 2022-03-16T00:00:00Z
2022-03-16
2023-01-20T15:59:42Z
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url http://hdl.handle.net/10773/35936
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10.1021/acs.iecr.1c04899
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dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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