Cinética de decomposição de líquidos iônicos dicatiônicos com ânions derivados de ácidos carboxílicos
Ano de defesa: | 2020 |
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Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , |
Tipo de documento: | Dissertação |
Tipo de acesso: | Acesso aberto |
Idioma: | por |
Instituição de defesa: |
Universidade Federal de Santa Maria
Centro de Ciências Naturais e Exatas |
Programa de Pós-Graduação: |
Programa de Pós-Graduação em Química
|
Departamento: |
Química
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País: |
Brasil
|
Palavras-chave em Português: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/22946 |
Resumo: | This work describes the synthesis, structural characterization, and thermal stability of eight dicationic ionic liquids (DILs) containing the cations 1,4-bis(3-methylimidazolium-1-yl)butane ([Bis(C4MIM)]2+) and 1,10-bis(3- methylimidazolium-1-yl)decane ([Bis(C10MIM)]2+) with the anions butyrate (C3COO-), pentanoate (C4COO-), hexanoate (C5COO-) and heptanoate (C6COO-) and two monocationic ionic liquids (MILs) containing the cation 3-methyl-1-butylimidazolium (C4MIM+) and the anions pentanoate and hexanoate. The thermal characterization of these ILs by TGA showed that DILs with the cation [Bis(C4MIM)]2+ are more stable than DILs with the cation [Bis(C10MIM)]2+ and the MILs, the latter being similar. Only for the DILs with the cation [Bis(C4MIM)]2+ an increase in the anion alkyl chain lead to an increase in thermal stability. DSC analysis (-80 to 130 ° C) showed that the DILs with the cation [Bis(C4MIM)]2+ and the MILs are amorphous solids, while most of the DILs with the cation [Bis(C10MIM)]2+are crystalline solids. The decomposition kinetics of the DILs [bis(C4MIM)][C3COO]2, [Bis(C4MIM)][C6COO]2 and [Bis(C10MIM)][C3COO]2 were analyzed by isothermal and isoconversional methodologies. The isoconversional methodologies were the Friedman, Osawa-Flynn-Wall (OFW) and Kissinger-Akahira-Sunose (KAS). The results of the isothermal analyses indicated that the zero-order reaction model best describes the experimental data. Also, the Ea values indicate that the [Bis(C4MIM)][C3COO]2 has a higher decomposition rate than the others, indicating that the velocity of decomposition is proportional to the molar mass of the ILs. The IL [Bis(C4MIM)][C6COO]2 presented two well-defined decomposition steps in isoconversional analyzes. For this methodology, it was also found that the thermal stability of the ILs is proportional to their molar masses. Ea values varied with conversion indicating that the decomposition of these DILs occurs in several steps, except for the first decomposition step of IL [Bis(C4MIM)][C6COO]2. The lnA value for the first decomposition step of this IL was determined by the compensation effect and the f(α) function follows a similar trend to the theoretical diffusion models. The decomposition products of the isothermal analysis of the DILs [bis(C4MIM)][C3COO]2 and [bis(C10MIM)][C3COO]2 were analyzed by 1H RMN and ESI-MS. In turn, non-isothermal decomposition products were analyzed using TGA-FTIR. The data showed that the DIL [bis(C4MIM)][C3COO]2 decomposes by SN2, E2, and heterocyclic carbenes formation reactions. For the DIL [bis(C10MIM)][C3COO]2 it was not possible to identify the mechanisms of isothermal decomposition. In the case of non-isothermal decomposition, esters were form as products, suggesting that the decomposition occurs by SN2 reactions |
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oai:repositorio.ufsm.br:1/22946 |
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Biblioteca Digital de Teses e Dissertações do UFSM |
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2021-11-24T12:21:04Z2021-11-24T12:21:04Z2020-02-19http://repositorio.ufsm.br/handle/1/22946This work describes the synthesis, structural characterization, and thermal stability of eight dicationic ionic liquids (DILs) containing the cations 1,4-bis(3-methylimidazolium-1-yl)butane ([Bis(C4MIM)]2+) and 1,10-bis(3- methylimidazolium-1-yl)decane ([Bis(C10MIM)]2+) with the anions butyrate (C3COO-), pentanoate (C4COO-), hexanoate (C5COO-) and heptanoate (C6COO-) and two monocationic ionic liquids (MILs) containing the cation 3-methyl-1-butylimidazolium (C4MIM+) and the anions pentanoate and hexanoate. The thermal characterization of these ILs by TGA showed that DILs with the cation [Bis(C4MIM)]2+ are more stable than DILs with the cation [Bis(C10MIM)]2+ and the MILs, the latter being similar. Only for the DILs with the cation [Bis(C4MIM)]2+ an increase in the anion alkyl chain lead to an increase in thermal stability. DSC analysis (-80 to 130 ° C) showed that the DILs with the cation [Bis(C4MIM)]2+ and the MILs are amorphous solids, while most of the DILs with the cation [Bis(C10MIM)]2+are crystalline solids. The decomposition kinetics of the DILs [bis(C4MIM)][C3COO]2, [Bis(C4MIM)][C6COO]2 and [Bis(C10MIM)][C3COO]2 were analyzed by isothermal and isoconversional methodologies. The isoconversional methodologies were the Friedman, Osawa-Flynn-Wall (OFW) and Kissinger-Akahira-Sunose (KAS). The results of the isothermal analyses indicated that the zero-order reaction model best describes the experimental data. Also, the Ea values indicate that the [Bis(C4MIM)][C3COO]2 has a higher decomposition rate than the others, indicating that the velocity of decomposition is proportional to the molar mass of the ILs. The IL [Bis(C4MIM)][C6COO]2 presented two well-defined decomposition steps in isoconversional analyzes. For this methodology, it was also found that the thermal stability of the ILs is proportional to their molar masses. Ea values varied with conversion indicating that the decomposition of these DILs occurs in several steps, except for the first decomposition step of IL [Bis(C4MIM)][C6COO]2. The lnA value for the first decomposition step of this IL was determined by the compensation effect and the f(α) function follows a similar trend to the theoretical diffusion models. The decomposition products of the isothermal analysis of the DILs [bis(C4MIM)][C3COO]2 and [bis(C10MIM)][C3COO]2 were analyzed by 1H RMN and ESI-MS. In turn, non-isothermal decomposition products were analyzed using TGA-FTIR. The data showed that the DIL [bis(C4MIM)][C3COO]2 decomposes by SN2, E2, and heterocyclic carbenes formation reactions. For the DIL [bis(C10MIM)][C3COO]2 it was not possible to identify the mechanisms of isothermal decomposition. In the case of non-isothermal decomposition, esters were form as products, suggesting that the decomposition occurs by SN2 reactionsEste trabalho descreve a síntese, caracterização estrutural e estabilidade térmica de oito Líquidos Iônicos Dicatiônicos (LIDs) contendo os cátions 1,4-bis(3-metilimidazolil-1-íneo)butano ([Bis(C4MIM)]2+) e 1,10-bis(3-metilimidazolil-1-íneo)decano ([Bis(C10MIM)]2+) e os ânions butirato (C3COO-), pentanoato (C4COO-), hexanoato (C5COO-) e heptanoato (C6COO-) e dois Líquidos Iônicos Monocatiônicos (LIMs) contendo cátion 3-metil-1-butilimidazolíneo (C4MIM+) e os ânions pentanoato e hexanoato. A caracterização térmica desses LIs por TGA mostrou que os LIDs com o cátion ([Bis(C4MIM)]2+) são mais estáveis que os LIDs com o cátion ([Bis(C10MIM)]2+ e que os LIMs, sendo que os últimos possuem estabilidade térmica similar. Para os LIDs com o cátion [Bis(C4MIM)]2+ o aumento da cadeia do ânion levou ao aumento da estabilidade térmica. As análises de DSC (-80 até 130 °C) mostraram que os LIDs com o cátion [Bis(C4MIM)]2+ e os LIMs são sólidos amorfos, enquanto que os LIDs com o cátion [Bis(C10MIM)]2+ comportaram-se como sólidos cristalinos. A cinética de decomposição dos LIDs [Bis(C4MIM)][C3COO]2, [Bis(C4MIM)][C6COO]2 e [Bis(C10MIM)][C3COO]2 foram determinadas usando metodologias isotérmicas e isoconversionais. Os métodos isoconversionais utilizados foram os de Friedman, Osawa-Flynn-Wall (OFW) e Kissinger-Akahira-Sunose (KAS). Os resultados das análises isotérmicas indicaram que o modelo ordem de reação com ordem igual a zero é o que melhor descreve os dados experimentais. Além disso, os valores de Ea determinados para os LIDs indicaram que o [Bis(C4MIM)][C3COO]2 se decompõe mais rapidamente (possui menor Ea), indicando que a velocidade de decomposição é proporcional à massa molar dos LIs. O [Bis(C4MIM)][C6COO]2 apresentou duas etapas bem definidas de decomposição nas análises isoconversionais. Os resultados desta análise também mostraram que a estabilidade dos LIs é proporcional às suas massas molares. Os valores de Ea variaram com a conversão indicando que a decomposição dos LIDs ocorre em múltiplas etapas. Exceto para a primeira etapa de decomposição do [Bis(C4MIM)][C6COO]2. Os valores de lnA para a primeira etapa de decomposição do LI [Bis(C4MIM)][C6COO]2 foram determinados pelo efeito de compensação. Para o mesmo LI e mesma etapa determinou-se que a função f(α) segue uma tendência similar aos modelos teóricos de difusão. Os produtos de decomposição da análise isotérmica dos LIDs [Bis(C4MIM)][C3COO]2 e [Bis(C10MIM)][C3COO]2 foram analisados por RMN de 1H e ESI-MS. Por sua vez, os produtos de decomposição não isotérmica foram analisados utilizando TGA-FTIR. Os dados mostraram que o LID [Bis(C4MIM)][C3COO]2 se decompõe por reações de SN2, E2 e formação de carbenos heterocíclicos. Para o LI [Bis(C10MIM)][C3COO]2 não foi possível identificar os mecanismos de decomposição isotérmica. No caso da decomposição não isotérmica se verificou a formação de ésteres como produtos, sugerindo que a decomposição ocorre por reações de SN2.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESporUniversidade Federal de Santa MariaCentro de Ciências Naturais e ExatasPrograma de Pós-Graduação em QuímicaUFSMBrasilQuímicaAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessLíquidos iônicos dicatiônicosCinética de decomposiçãoCarboxilatoDicationic ionic liquidsDecomposition kineticsCarboxylateCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICACinética de decomposição de líquidos iônicos dicatiônicos com ânions derivados de ácidos carboxílicosDecomposition kinetics of dicationic ionic liquids with carboxylic acid derived anionsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisFrizzo, Clarissa Piccininhttp://lattes.cnpq.br/0029279904716491Bonacorso, Helio GauzeVerly, Rodrigo Moreirahttp://lattes.cnpq.br/8219963144747335Vieira, Jean Carlos Bauer1006000000006006006008339c8fa-17c5-4531-bcb5-111d15cb015cf7723771-900a-4ab1-8970-71b2e6db0401dbcce58b-96b0-4f45-a78d-ca6f339e038d2d7f845c-4de6-407a-bced-015b4a47974breponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALDIS_PPGQUIMICA_2020_VIEIRA_JEAN.pdfDIS_PPGQUIMICA_2020_VIEIRA_JEAN.pdfDissertação de Mestradoapplication/pdf7532891http://repositorio.ufsm.br/bitstream/1/22946/1/DIS_PPGQUIMICA_2020_VIEIRA_JEAN.pdf2c2cc2601fcc3f8e68c5355848c4aea3MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Cinética de decomposição de líquidos iônicos dicatiônicos com ânions derivados de ácidos carboxílicos |
dc.title.alternative.eng.fl_str_mv |
Decomposition kinetics of dicationic ionic liquids with carboxylic acid derived anions |
title |
Cinética de decomposição de líquidos iônicos dicatiônicos com ânions derivados de ácidos carboxílicos |
spellingShingle |
Cinética de decomposição de líquidos iônicos dicatiônicos com ânions derivados de ácidos carboxílicos Vieira, Jean Carlos Bauer Líquidos iônicos dicatiônicos Cinética de decomposição Carboxilato Dicationic ionic liquids Decomposition kinetics Carboxylate CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Cinética de decomposição de líquidos iônicos dicatiônicos com ânions derivados de ácidos carboxílicos |
title_full |
Cinética de decomposição de líquidos iônicos dicatiônicos com ânions derivados de ácidos carboxílicos |
title_fullStr |
Cinética de decomposição de líquidos iônicos dicatiônicos com ânions derivados de ácidos carboxílicos |
title_full_unstemmed |
Cinética de decomposição de líquidos iônicos dicatiônicos com ânions derivados de ácidos carboxílicos |
title_sort |
Cinética de decomposição de líquidos iônicos dicatiônicos com ânions derivados de ácidos carboxílicos |
author |
Vieira, Jean Carlos Bauer |
author_facet |
Vieira, Jean Carlos Bauer |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Frizzo, Clarissa Piccinin |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/0029279904716491 |
dc.contributor.referee1.fl_str_mv |
Bonacorso, Helio Gauze |
dc.contributor.referee2.fl_str_mv |
Verly, Rodrigo Moreira |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/8219963144747335 |
dc.contributor.author.fl_str_mv |
Vieira, Jean Carlos Bauer |
contributor_str_mv |
Frizzo, Clarissa Piccinin Bonacorso, Helio Gauze Verly, Rodrigo Moreira |
dc.subject.por.fl_str_mv |
Líquidos iônicos dicatiônicos Cinética de decomposição Carboxilato |
topic |
Líquidos iônicos dicatiônicos Cinética de decomposição Carboxilato Dicationic ionic liquids Decomposition kinetics Carboxylate CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Dicationic ionic liquids Decomposition kinetics Carboxylate |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This work describes the synthesis, structural characterization, and thermal stability of eight dicationic ionic liquids (DILs) containing the cations 1,4-bis(3-methylimidazolium-1-yl)butane ([Bis(C4MIM)]2+) and 1,10-bis(3- methylimidazolium-1-yl)decane ([Bis(C10MIM)]2+) with the anions butyrate (C3COO-), pentanoate (C4COO-), hexanoate (C5COO-) and heptanoate (C6COO-) and two monocationic ionic liquids (MILs) containing the cation 3-methyl-1-butylimidazolium (C4MIM+) and the anions pentanoate and hexanoate. The thermal characterization of these ILs by TGA showed that DILs with the cation [Bis(C4MIM)]2+ are more stable than DILs with the cation [Bis(C10MIM)]2+ and the MILs, the latter being similar. Only for the DILs with the cation [Bis(C4MIM)]2+ an increase in the anion alkyl chain lead to an increase in thermal stability. DSC analysis (-80 to 130 ° C) showed that the DILs with the cation [Bis(C4MIM)]2+ and the MILs are amorphous solids, while most of the DILs with the cation [Bis(C10MIM)]2+are crystalline solids. The decomposition kinetics of the DILs [bis(C4MIM)][C3COO]2, [Bis(C4MIM)][C6COO]2 and [Bis(C10MIM)][C3COO]2 were analyzed by isothermal and isoconversional methodologies. The isoconversional methodologies were the Friedman, Osawa-Flynn-Wall (OFW) and Kissinger-Akahira-Sunose (KAS). The results of the isothermal analyses indicated that the zero-order reaction model best describes the experimental data. Also, the Ea values indicate that the [Bis(C4MIM)][C3COO]2 has a higher decomposition rate than the others, indicating that the velocity of decomposition is proportional to the molar mass of the ILs. The IL [Bis(C4MIM)][C6COO]2 presented two well-defined decomposition steps in isoconversional analyzes. For this methodology, it was also found that the thermal stability of the ILs is proportional to their molar masses. Ea values varied with conversion indicating that the decomposition of these DILs occurs in several steps, except for the first decomposition step of IL [Bis(C4MIM)][C6COO]2. The lnA value for the first decomposition step of this IL was determined by the compensation effect and the f(α) function follows a similar trend to the theoretical diffusion models. The decomposition products of the isothermal analysis of the DILs [bis(C4MIM)][C3COO]2 and [bis(C10MIM)][C3COO]2 were analyzed by 1H RMN and ESI-MS. In turn, non-isothermal decomposition products were analyzed using TGA-FTIR. The data showed that the DIL [bis(C4MIM)][C3COO]2 decomposes by SN2, E2, and heterocyclic carbenes formation reactions. For the DIL [bis(C10MIM)][C3COO]2 it was not possible to identify the mechanisms of isothermal decomposition. In the case of non-isothermal decomposition, esters were form as products, suggesting that the decomposition occurs by SN2 reactions |
publishDate |
2020 |
dc.date.issued.fl_str_mv |
2020-02-19 |
dc.date.accessioned.fl_str_mv |
2021-11-24T12:21:04Z |
dc.date.available.fl_str_mv |
2021-11-24T12:21:04Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
format |
masterThesis |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/22946 |
url |
http://repositorio.ufsm.br/handle/1/22946 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
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Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
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Brasil |
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Química |
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Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
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