Novel approach on the synthesis of starch betainate by transesterification

Detalhes bibliográficos
Autor(a) principal: Sharma, Mohit
Data de Publicação: 2021
Outros Autores: Aguado, Roberto, Murtinho, Dina, Valente, Artur J. M., Ferreira, Paulo J.
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.
id RCAP_dad2786cbbad1a6a3359fb0cd4d32e1e
oai_identifier_str oai:estudogeral.uc.pt:10316/107449
network_acronym_str RCAP
network_name_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository_id_str 7160
spelling 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
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
_version_ 1799134124432162816