Novel approach on the synthesis of starch betainate by transesterification
Autor(a) principal: | |
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Data de Publicação: | 2021 |
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/10316/107449 https://doi.org/10.1016/j.ijbiomac.2021.05.175 |
Resumo: | Transesterification of starch with methyl betainate was studied for the first time, both in aprotic media and in solid state, and both under alkaline and acidic conditions. Betaine hydrochloride was first esterified in methanol, attaining a conversion of 86%. Starch was then converted into starch betainate in either N,N-dimethylformamide or dimethyl sulfoxide, and using sulfuric acid as catalyst or pre-activating the polymer in NaOH/ethanol. Furthermore, solid-state transesterification was carried out in a ball mill, for which sulfuric acid was replaced with the less corrosive sulfamic acid. Cationic starch esters were characterised by 1H and 13C NMR spectroscopy, infrared spectroscopy, thermogravimetric analysis, viscometry, optical microscopy (in water) and scanning electron microscopy (dry). In solution, the process attained degrees of substitution up to 0.4. No by-products, dehydration, oxidation or colouring were detected, but starch underwent severe depolymerization in wet media. In solid state, whilst the resulting degree of substitution was lower, degradation was minimal. In any case, transesterification, with its variety of possibilities, yields cationic starches that offer a promising alternative to conventional ethers. |
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Novel approach on the synthesis of starch betainate by transesterificationBetaine methyl esterStarch betainateTransesterificationBetaineCatalysisEsterificationMagnetic Resonance SpectroscopyMicroscopy, Electron, ScanningOxidation-ReductionStarchTransesterification of starch with methyl betainate was studied for the first time, both in aprotic media and in solid state, and both under alkaline and acidic conditions. Betaine hydrochloride was first esterified in methanol, attaining a conversion of 86%. Starch was then converted into starch betainate in either N,N-dimethylformamide or dimethyl sulfoxide, and using sulfuric acid as catalyst or pre-activating the polymer in NaOH/ethanol. Furthermore, solid-state transesterification was carried out in a ball mill, for which sulfuric acid was replaced with the less corrosive sulfamic acid. Cationic starch esters were characterised by 1H and 13C NMR spectroscopy, infrared spectroscopy, thermogravimetric analysis, viscometry, optical microscopy (in water) and scanning electron microscopy (dry). In solution, the process attained degrees of substitution up to 0.4. No by-products, dehydration, oxidation or colouring were detected, but starch underwent severe depolymerization in wet media. In solid state, whilst the resulting degree of substitution was lower, degradation was minimal. In any case, transesterification, with its variety of possibilities, yields cationic starches that offer a promising alternative to conventional ethers.This work was carried out under the Project inpactus -innovative products and technologies from eucalyptus, Project N.° 21874 funded by Portugal 2020 through European Regional Development Fund (ERDF) in the frame of COMPETE 2020 n°246/AXIS II/2017. Authors would like to thank the Coimbra Chemical Centre, which is supported by the Fundação para a Ciência e a Tecnologia (FCT), through the projects UID/QUI/00313/2020 and COMPETE. Authors would also like to thank the CIEPQPF - Strategic Research Centre Project UIDB/00102/ 2020, funded by the Fundação para a Ciência e Tecnologia (FCT). M.S. acknowledges the PhD grant BDE 03|POCI-01-0247-FEDER-021874. R.A. acknowledges the post-doc grant BPD 02|POCI-01-0247-FEDER- 021874.Elsevier2021-07-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://hdl.handle.net/10316/107449http://hdl.handle.net/10316/107449https://doi.org/10.1016/j.ijbiomac.2021.05.175eng01418130Sharma, MohitAguado, RobertoMurtinho, DinaValente, Artur J. M.Ferreira, Paulo J.info: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:RCAAP2023-07-17T08:49:37Zoai:estudogeral.uc.pt:10316/107449Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T21:23:48.306242Repositório 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 |
Novel approach on the synthesis of starch betainate by transesterification |
title |
Novel approach on the synthesis of starch betainate by transesterification |
spellingShingle |
Novel approach on the synthesis of starch betainate by transesterification Sharma, Mohit Betaine methyl ester Starch betainate Transesterification Betaine Catalysis Esterification Magnetic Resonance Spectroscopy Microscopy, Electron, Scanning Oxidation-Reduction Starch |
title_short |
Novel approach on the synthesis of starch betainate by transesterification |
title_full |
Novel approach on the synthesis of starch betainate by transesterification |
title_fullStr |
Novel approach on the synthesis of starch betainate by transesterification |
title_full_unstemmed |
Novel approach on the synthesis of starch betainate by transesterification |
title_sort |
Novel approach on the synthesis of starch betainate by transesterification |
author |
Sharma, Mohit |
author_facet |
Sharma, Mohit Aguado, Roberto Murtinho, Dina Valente, Artur J. M. Ferreira, Paulo J. |
author_role |
author |
author2 |
Aguado, Roberto Murtinho, Dina Valente, Artur J. M. Ferreira, Paulo J. |
author2_role |
author author author author |
dc.contributor.author.fl_str_mv |
Sharma, Mohit Aguado, Roberto Murtinho, Dina Valente, Artur J. M. Ferreira, Paulo J. |
dc.subject.por.fl_str_mv |
Betaine methyl ester Starch betainate Transesterification Betaine Catalysis Esterification Magnetic Resonance Spectroscopy Microscopy, Electron, Scanning Oxidation-Reduction Starch |
topic |
Betaine methyl ester Starch betainate Transesterification Betaine Catalysis Esterification Magnetic Resonance Spectroscopy Microscopy, Electron, Scanning Oxidation-Reduction Starch |
description |
Transesterification of starch with methyl betainate was studied for the first time, both in aprotic media and in solid state, and both under alkaline and acidic conditions. Betaine hydrochloride was first esterified in methanol, attaining a conversion of 86%. Starch was then converted into starch betainate in either N,N-dimethylformamide or dimethyl sulfoxide, and using sulfuric acid as catalyst or pre-activating the polymer in NaOH/ethanol. Furthermore, solid-state transesterification was carried out in a ball mill, for which sulfuric acid was replaced with the less corrosive sulfamic acid. Cationic starch esters were characterised by 1H and 13C NMR spectroscopy, infrared spectroscopy, thermogravimetric analysis, viscometry, optical microscopy (in water) and scanning electron microscopy (dry). In solution, the process attained degrees of substitution up to 0.4. No by-products, dehydration, oxidation or colouring were detected, but starch underwent severe depolymerization in wet media. In solid state, whilst the resulting degree of substitution was lower, degradation was minimal. In any case, transesterification, with its variety of possibilities, yields cationic starches that offer a promising alternative to conventional ethers. |
publishDate |
2021 |
dc.date.none.fl_str_mv |
2021-07-01 |
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/10316/107449 http://hdl.handle.net/10316/107449 https://doi.org/10.1016/j.ijbiomac.2021.05.175 |
url |
http://hdl.handle.net/10316/107449 https://doi.org/10.1016/j.ijbiomac.2021.05.175 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
01418130 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Elsevier |
publisher.none.fl_str_mv |
Elsevier |
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 |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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RCAAP |
institution |
RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
collection |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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1799134124432162816 |