Estudo da atividade catalítica do óxido de grafite em reações orgânicas
Autor(a) principal: | |
---|---|
Data de Publicação: | 2021 |
Tipo de documento: | Tese |
Idioma: | por |
Título da fonte: | Repositório Institucional da UFG |
Texto Completo: | http://repositorio.bc.ufg.br/tede/handle/tede/11875 |
Resumo: | Graphite oxide (OGt) is characterized as graphite sheets with randomly distributed aromatic regions (sp2 carbon atoms) and oxygenated aliphatic regions (sp3 carbon atoms); has different functional groups such as hydroxyl, epoxy and carboxyl. The presence of these groups confers an acidic character to the material and, due to its biocompatibility, easy reuse, it can be considered a promising heterogeneous catalyst. Thus, we sought to use graphite oxide as an acid catalyst for the following organic reactions: Pechmann, reaction of disubstituted benzimidazoles, Mannich and Biginelli-like. To obtain graphite oxide, the Hummers method was used, in which graphite is oxidized involving a mixture of sodium nitrate, potassium permanganate and concentrated sulfuric acid; however, the methodology is a time-consuming and low-yield process. Thus, the graphite oxide was characterized by X-ray diffraction, IR spectroscopy, thermogravimetic analysis and by electron microscopy, which allowed to evaluate the oxidation process of graphite in graphite oxide. In this study, the reactions were analyzed in many parameters, such as: temperature, stoichiometric ratio, solvents, and amount of catalyst. Thus, when testing graphite oxide in these reactions, it was observed that OGt presented different behavior in each type of reaction; it was found that for the disubstituted benzimidazoles only 30 mg were needed to obtain a yield greater than 80%, while for the Biginelli-like reaction 300 mg was used and a yield below 80% was obtained. However, conditions were sought in which the reactions occurred in the absence of solvent, in order to make the processes environmentally friendly with the use of graphite oxide as a heterogeneous solid catalyst. Furthermore, the variation of substrates was evaluated for all reactions, which allowed us to observe that the best yields occurred with substrates in the presence of electron activating groups, while for the Pechmann, Mannich and Biginelli-like reactions there was no formation of products with an electron-withdrawing group -NO2. All products were characterized by 1H and 13C NMR and were identified by comparison with the spectra reported in the literature. |
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Oliveira, Guilherme Roberto dehttp://lattes.cnpq.br/8239498431579015Alonso, Christian Gonçalveshttp://lattes.cnpq.br/7285754665946583Oliveira, Guilherme Roberto deSilva, Valter Henrique CarvalhoChagas, Rafael Pavão dasPerez, Caridad NodaCosta, Maísa Borgeshttp://lattes.cnpq.br/2330577601304742Naves, Raquel Ferreira2022-02-02T11:14:52Z2022-02-02T11:14:52Z2021-12-14NAVES, Raquel Ferreira. Estudo da atividade catalítica do óxido de grafite em reações orgânicas. 2021. 238 f. Tese (Doutorado em Química). Universidade Federal de Goiás, Goiânia, 2021.http://repositorio.bc.ufg.br/tede/handle/tede/11875ark:/38995/0013000007czqGraphite oxide (OGt) is characterized as graphite sheets with randomly distributed aromatic regions (sp2 carbon atoms) and oxygenated aliphatic regions (sp3 carbon atoms); has different functional groups such as hydroxyl, epoxy and carboxyl. The presence of these groups confers an acidic character to the material and, due to its biocompatibility, easy reuse, it can be considered a promising heterogeneous catalyst. Thus, we sought to use graphite oxide as an acid catalyst for the following organic reactions: Pechmann, reaction of disubstituted benzimidazoles, Mannich and Biginelli-like. To obtain graphite oxide, the Hummers method was used, in which graphite is oxidized involving a mixture of sodium nitrate, potassium permanganate and concentrated sulfuric acid; however, the methodology is a time-consuming and low-yield process. Thus, the graphite oxide was characterized by X-ray diffraction, IR spectroscopy, thermogravimetic analysis and by electron microscopy, which allowed to evaluate the oxidation process of graphite in graphite oxide. In this study, the reactions were analyzed in many parameters, such as: temperature, stoichiometric ratio, solvents, and amount of catalyst. Thus, when testing graphite oxide in these reactions, it was observed that OGt presented different behavior in each type of reaction; it was found that for the disubstituted benzimidazoles only 30 mg were needed to obtain a yield greater than 80%, while for the Biginelli-like reaction 300 mg was used and a yield below 80% was obtained. However, conditions were sought in which the reactions occurred in the absence of solvent, in order to make the processes environmentally friendly with the use of graphite oxide as a heterogeneous solid catalyst. Furthermore, the variation of substrates was evaluated for all reactions, which allowed us to observe that the best yields occurred with substrates in the presence of electron activating groups, while for the Pechmann, Mannich and Biginelli-like reactions there was no formation of products with an electron-withdrawing group -NO2. All products were characterized by 1H and 13C NMR and were identified by comparison with the spectra reported in the literature.O óxido de grafite (OGt) é caracterizado como folhas de grafite com regiões aromáticas distribuídas aleatoriamente (átomos de carbono sp2) e regiões alifáticas oxigenadas (átomos de carbono sp3); apresenta diferentes grupos funcionais como hidroxila, epóxi e carboxilas. A presença desses grupos confere caráter ácido ao material e, devido a sua biocompatibilidade, fácil reutilização, pode ser considerado um promissor catalisador heterogêneo. Assim, buscou-se a utilização do óxido de grafite, como catalisador ácido para as seguintes reações orgânicas: Pechmann, reação dos benzimidazóis dissubstituídos, Mannich e Biginelli-like. Para a obtenção do óxido de grafite empregou-se o método Hummers, no qual o grafite é oxidado envolvendo uma mistura de nitrato de sódio, permanganato de potássio e ácido sulfúrico concentrado; porém, a metodologia é um processo demorado e de baixo rendimento. Assim, o óxido de grafite foi caracterizado por difração de raios-X, espectroscopia de IV, análise termogravimética e por microscopia eletrônica, o que permitiu avaliar o processo oxidativo do grafite em óxido de grafite. Neste estudo, as reações foram analisadas em muitos parâmetros, tais como: temperatura, razão estequiométrica, solventes, e quantidade de catalisador. Dessa maneira, ao testar o óxido de grafite nessas reações observou-se que o OGt apresentou comportamento diferenciado em cada tipo de reação; constatou-se que para os benzimidazóis dissubstituído foram necessários apenas 30 mg para obter um rendimento superior a 80%, enquanto para a reação de Biginelli-like utilizou-se 300 mg e obteve-se um rendimento abaixo de 80%. Porém, buscou-se condições no qual as reações ocorressem na ausência de solvente, com o intuito de tornar os processos ambientalmente corretos com a utilização do óxido de grafite como catalisador sólido heterogêneo. Além do mais, avaliou-se a variação de substratos para todas as reações, o que permitiu observar que os melhores rendimentos ocorreram com substratos na presença de grupos ativadores de elétrons, enquanto para as reações de Pechmann, Mannich e Biginelli-like não houve a formação de produtos com grupo -NO2, retirador de elétrons. Todos os produtos foram caracterizados por RMN 1H e 13C e foram identificados pela comparação com os espectros relatados na literatura.Submitted by Leandro Machado (leandromachado@ufg.br) on 2022-02-01T16:30:48Z No. of bitstreams: 2 Tese-Raquel Ferreira Naves-2021.pdf: 5187177 bytes, checksum: bcfcafe6ea711105d704d481f154f561 (MD5) license_rdf: 805 bytes, checksum: 4460e5956bc1d1639be9ae6146a50347 (MD5)Approved for entry into archive by Liliane Ferreira (ljuvencia30@gmail.com) on 2022-02-02T11:14:52Z (GMT) No. of bitstreams: 2 Tese-Raquel Ferreira Naves-2021.pdf: 5187177 bytes, checksum: bcfcafe6ea711105d704d481f154f561 (MD5) license_rdf: 805 bytes, checksum: 4460e5956bc1d1639be9ae6146a50347 (MD5)Made available in DSpace on 2022-02-02T11:14:52Z (GMT). No. of bitstreams: 2 Tese-Raquel Ferreira Naves-2021.pdf: 5187177 bytes, checksum: bcfcafe6ea711105d704d481f154f561 (MD5) license_rdf: 805 bytes, checksum: 4460e5956bc1d1639be9ae6146a50347 (MD5) Previous issue date: 2021-12-14Fundação de Amparo à Pesquisa do Estado de GoiásporUniversidade Federal de GoiásPrograma de Pós-graduação em Química (IQ)UFGBrasilInstituto de Química - IQ (RG)Attribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessÓxido de grafiteCatalisadorReações orgânicasOrganic reactionsGraphite oxideCatalystCIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICAEstudo da atividade catalítica do óxido de grafite em reações orgânicasStudy of the catalytyc activity of grphite oxide in organic reactionsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesis825005005005002910953reponame:Repositório Institucional da UFGinstname:Universidade Federal de Goiás (UFG)instacron:UFGLICENSElicense.txtlicense.txttext/plain; charset=utf-81748http://repositorio.bc.ufg.br/tede/bitstreams/c2fd47fc-0190-4797-8248-49250882d1c0/download8a4605be74aa9ea9d79846c1fba20a33MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8805http://repositorio.bc.ufg.br/tede/bitstreams/f5ad4fec-3add-4694-a8f6-8af1312c8412/download4460e5956bc1d1639be9ae6146a50347MD52ORIGINALTese-Raquel Ferreira Naves-2021.pdfTese-Raquel Ferreira Naves-2021.pdfapplication/pdf5187177http://repositorio.bc.ufg.br/tede/bitstreams/55db2607-156e-42bd-8e4d-6cbe75a23029/downloadbcfcafe6ea711105d704d481f154f561MD53tede/118752022-02-02 08:14:52.938http://creativecommons.org/licenses/by-nc-nd/4.0/Attribution-NonCommercial-NoDerivatives 4.0 Internationalopen.accessoai:repositorio.bc.ufg.br:tede/11875http://repositorio.bc.ufg.br/tedeRepositório InstitucionalPUBhttp://repositorio.bc.ufg.br/oai/requesttasesdissertacoes.bc@ufg.bropendoar:2022-02-02T11:14:52Repositório Institucional da UFG - Universidade Federal de Goiás (UFG)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 |
dc.title.pt_BR.fl_str_mv |
Estudo da atividade catalítica do óxido de grafite em reações orgânicas |
dc.title.alternative.eng.fl_str_mv |
Study of the catalytyc activity of grphite oxide in organic reactions |
title |
Estudo da atividade catalítica do óxido de grafite em reações orgânicas |
spellingShingle |
Estudo da atividade catalítica do óxido de grafite em reações orgânicas Naves, Raquel Ferreira Óxido de grafite Catalisador Reações orgânicas Organic reactions Graphite oxide Catalyst CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA |
title_short |
Estudo da atividade catalítica do óxido de grafite em reações orgânicas |
title_full |
Estudo da atividade catalítica do óxido de grafite em reações orgânicas |
title_fullStr |
Estudo da atividade catalítica do óxido de grafite em reações orgânicas |
title_full_unstemmed |
Estudo da atividade catalítica do óxido de grafite em reações orgânicas |
title_sort |
Estudo da atividade catalítica do óxido de grafite em reações orgânicas |
author |
Naves, Raquel Ferreira |
author_facet |
Naves, Raquel Ferreira |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Oliveira, Guilherme Roberto de |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/8239498431579015 |
dc.contributor.advisor-co1.fl_str_mv |
Alonso, Christian Gonçalves |
dc.contributor.advisor-co1Lattes.fl_str_mv |
http://lattes.cnpq.br/7285754665946583 |
dc.contributor.referee1.fl_str_mv |
Oliveira, Guilherme Roberto de |
dc.contributor.referee2.fl_str_mv |
Silva, Valter Henrique Carvalho |
dc.contributor.referee3.fl_str_mv |
Chagas, Rafael Pavão das |
dc.contributor.referee4.fl_str_mv |
Perez, Caridad Noda |
dc.contributor.referee5.fl_str_mv |
Costa, Maísa Borges |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/2330577601304742 |
dc.contributor.author.fl_str_mv |
Naves, Raquel Ferreira |
contributor_str_mv |
Oliveira, Guilherme Roberto de Alonso, Christian Gonçalves Oliveira, Guilherme Roberto de Silva, Valter Henrique Carvalho Chagas, Rafael Pavão das Perez, Caridad Noda Costa, Maísa Borges |
dc.subject.por.fl_str_mv |
Óxido de grafite Catalisador Reações orgânicas Organic reactions |
topic |
Óxido de grafite Catalisador Reações orgânicas Organic reactions Graphite oxide Catalyst CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA |
dc.subject.eng.fl_str_mv |
Graphite oxide Catalyst |
dc.subject.cnpq.fl_str_mv |
CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA |
description |
Graphite oxide (OGt) is characterized as graphite sheets with randomly distributed aromatic regions (sp2 carbon atoms) and oxygenated aliphatic regions (sp3 carbon atoms); has different functional groups such as hydroxyl, epoxy and carboxyl. The presence of these groups confers an acidic character to the material and, due to its biocompatibility, easy reuse, it can be considered a promising heterogeneous catalyst. Thus, we sought to use graphite oxide as an acid catalyst for the following organic reactions: Pechmann, reaction of disubstituted benzimidazoles, Mannich and Biginelli-like. To obtain graphite oxide, the Hummers method was used, in which graphite is oxidized involving a mixture of sodium nitrate, potassium permanganate and concentrated sulfuric acid; however, the methodology is a time-consuming and low-yield process. Thus, the graphite oxide was characterized by X-ray diffraction, IR spectroscopy, thermogravimetic analysis and by electron microscopy, which allowed to evaluate the oxidation process of graphite in graphite oxide. In this study, the reactions were analyzed in many parameters, such as: temperature, stoichiometric ratio, solvents, and amount of catalyst. Thus, when testing graphite oxide in these reactions, it was observed that OGt presented different behavior in each type of reaction; it was found that for the disubstituted benzimidazoles only 30 mg were needed to obtain a yield greater than 80%, while for the Biginelli-like reaction 300 mg was used and a yield below 80% was obtained. However, conditions were sought in which the reactions occurred in the absence of solvent, in order to make the processes environmentally friendly with the use of graphite oxide as a heterogeneous solid catalyst. Furthermore, the variation of substrates was evaluated for all reactions, which allowed us to observe that the best yields occurred with substrates in the presence of electron activating groups, while for the Pechmann, Mannich and Biginelli-like reactions there was no formation of products with an electron-withdrawing group -NO2. All products were characterized by 1H and 13C NMR and were identified by comparison with the spectra reported in the literature. |
publishDate |
2021 |
dc.date.issued.fl_str_mv |
2021-12-14 |
dc.date.accessioned.fl_str_mv |
2022-02-02T11:14:52Z |
dc.date.available.fl_str_mv |
2022-02-02T11:14:52Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/doctoralThesis |
format |
doctoralThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
NAVES, Raquel Ferreira. Estudo da atividade catalítica do óxido de grafite em reações orgânicas. 2021. 238 f. Tese (Doutorado em Química). Universidade Federal de Goiás, Goiânia, 2021. |
dc.identifier.uri.fl_str_mv |
http://repositorio.bc.ufg.br/tede/handle/tede/11875 |
dc.identifier.dark.fl_str_mv |
ark:/38995/0013000007czq |
identifier_str_mv |
NAVES, Raquel Ferreira. Estudo da atividade catalítica do óxido de grafite em reações orgânicas. 2021. 238 f. Tese (Doutorado em Química). Universidade Federal de Goiás, Goiânia, 2021. ark:/38995/0013000007czq |
url |
http://repositorio.bc.ufg.br/tede/handle/tede/11875 |
dc.language.iso.fl_str_mv |
por |
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por |
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82 |
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29 |
dc.relation.cnpq.fl_str_mv |
1095 |
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3 |
dc.rights.driver.fl_str_mv |
Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Universidade Federal de Goiás |
dc.publisher.program.fl_str_mv |
Programa de Pós-graduação em Química (IQ) |
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UFG |
dc.publisher.country.fl_str_mv |
Brasil |
dc.publisher.department.fl_str_mv |
Instituto de Química - IQ (RG) |
publisher.none.fl_str_mv |
Universidade Federal de Goiás |
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