Sistemas catalíticos heterogêneos para reações de acoplamento Stille-Migita
Ano de defesa: | 2019 |
---|---|
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 Goiás
|
Programa de Pós-Graduação: |
Programa de Pós-graduação em Engenharia Química (IQ)
|
Departamento: |
Instituto de Química - IQ (RG)
|
País: |
Brasil
|
Palavras-chave em Português: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.bc.ufg.br/tede/handle/tede/10047 |
Resumo: | Carbon-carbon coupling reactions are of fundamental importance in the synthesis of organic compounds. The Stille-Migita reaction is a cross-coupling reaction and occurs when an organotin compound and an organic halide hybridized to sp3 react under the presence of a metal-based catalyst, generally palladium. The reaction has the advantage of being compatible with virtually any functional group and for forming products with complex chains, such as pharmaceuticals and agrochemicals. However, Stille synthesis is usually performed by homogeneous catalysis, which enhances the need for costly purification processes necessary to remove metal debris from the reaction products. Thus, this work synthesized and verified the use of heterogeneous catalysts for Stille coupling reactions, using the efficient and economical method of wet impregnation in its preparation by producing monometallic catalysts with different oxides as support. The catalysts were characterized before and after calcination by thermogravimetry and differential thermal analysis (TG / DTA), X-ray diffraction (XRD), Scanning Electron Microscopy (SEM), textural analysis by adsorption/desorption isotherms of N2 and X-ray fluorescence (XRF). The reaction parameters were optimized: time, temperature, type of solvent and catalyst composition. The materials La2O3/Pd and TiO2/Pd showed no catalytic activity, whereas the catalysts Nb2O5/Pd and SiO2/Pd showed good conversions, above 80%. The recycling tests showed considerable loss of activity, which could be associated with filtration and leaching of the active phase between cycles. Nb2O5/Pd showed higher efficiency in the presence of non-toxic solvents (water/ethanol), unusual in Stille reactions. It is expected that this work will contribute to the development of heterogeneous catalysis, particularly in the coupling reactions, since economical methods of synthesis have produced catalytically active materials. |
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Alonso, Christian Gonçalveshttp://lattes.cnpq.br/7285754665946583Oliveira, Guilherme Roberto dehttp://lattes.cnpq.br/8239498431579015Alonso, Christian GonçalvesOstroski, Indianara ConceiçãoChagas, Rafael Pavão dashttp://lattes.cnpq.br/5848031195446622Godoy, Pedro Henrique Machado2019-09-26T12:35:32Z2019-08-27GODOY, P. H. M. Sistemas catalíticos heterogêneos para reações de acoplamento Stille-Migita. 2019. 132 f. Dissertação (Mestrado em Engenharia Química) - Universidade Federal de Goiás, Goiânia, 2019.http://repositorio.bc.ufg.br/tede/handle/tede/10047Carbon-carbon coupling reactions are of fundamental importance in the synthesis of organic compounds. The Stille-Migita reaction is a cross-coupling reaction and occurs when an organotin compound and an organic halide hybridized to sp3 react under the presence of a metal-based catalyst, generally palladium. The reaction has the advantage of being compatible with virtually any functional group and for forming products with complex chains, such as pharmaceuticals and agrochemicals. However, Stille synthesis is usually performed by homogeneous catalysis, which enhances the need for costly purification processes necessary to remove metal debris from the reaction products. Thus, this work synthesized and verified the use of heterogeneous catalysts for Stille coupling reactions, using the efficient and economical method of wet impregnation in its preparation by producing monometallic catalysts with different oxides as support. The catalysts were characterized before and after calcination by thermogravimetry and differential thermal analysis (TG / DTA), X-ray diffraction (XRD), Scanning Electron Microscopy (SEM), textural analysis by adsorption/desorption isotherms of N2 and X-ray fluorescence (XRF). The reaction parameters were optimized: time, temperature, type of solvent and catalyst composition. The materials La2O3/Pd and TiO2/Pd showed no catalytic activity, whereas the catalysts Nb2O5/Pd and SiO2/Pd showed good conversions, above 80%. The recycling tests showed considerable loss of activity, which could be associated with filtration and leaching of the active phase between cycles. Nb2O5/Pd showed higher efficiency in the presence of non-toxic solvents (water/ethanol), unusual in Stille reactions. It is expected that this work will contribute to the development of heterogeneous catalysis, particularly in the coupling reactions, since economical methods of synthesis have produced catalytically active materials.As reações de acoplamento carbono-carbono ― ou reações de acoplamento cruzado ― são de fundamental importância na síntese de compostos orgânicos. A reação de Stille-Migita é uma reação de acoplamento cruzado e ocorre quando um composto de organoestanho e um haleto orgânico hibridizado em sp3 reagem sob a presença de um catalisador a base de metal, geralmente o paládio. A reação possui a vantagem de ser compatível com praticamente qualquer grupo funcional e por formar produtos com cadeias complexas, como produtos farmacêuticos e agroquímicos. Entretanto, a síntese de Stille é geralmente realizada mediante catálise homogênea, que intensifica a necessidade de processos de purificação dispendiosos necessários para remover restos de metais dos produtos da reação. Sendo assim, este trabalho teve como propósito sintetizar e verificar o uso de catalisadores heterogêneos para reações de acoplamento Stille, utilizando o método eficaz e econômico de impregnação por excesso de solvente em sua preparação e tendo como principal enfoque a produção de catalisadores monometálicos com diferentes óxidos como suporte. Os catalisadores foram caracterizados antes e após a calcinação por termogravimetria e análise térmica diferencial (TG/ATD), difração de raios X (DRX), Microscopia Eletrônica de Varredura (MEV), análise textural por isotermas de adsorção/dessorção de N2 e fluorescência de raios X (FRX). Os parâmetros reacionais foram verificados: tempo, temperatura, tipo de solvente e carga catalítica. Os materiais La2O3/Pd e TiO2/Pd não apresentaram atividade catalítica, enquanto que os catalisadores de Nb2O5/Pd e SiO2/Pd apresentaram boas conversões, acima de 80%. Os testes de reciclagem demonstraram considerável perda de atividade, possivelmente associadas a filtração e lixiviação da fase ativa entre ciclos. Nb2O5/Pd mostrou eficiência superior quando na presença de solventes não-tóxicos (água/etanol), incomum em reações de Stille. Por fim, espera-se que este trabalho contribua no desenvolvimento da catálise heterogênea, em particular nas reações de acoplamento, visto que métodos econômicos de síntese produziram materiais cataliticamente ativos.Submitted by Ana Caroline Costa (ana_caroline212@hotmail.com) on 2019-09-25T19:07:16Z No. of bitstreams: 2 Dissertação - Pedro Henrique Machado Godoy - 2019.pdf: 3208046 bytes, checksum: e124c90ecb9122aab193fbfefddfd9dd (MD5) license_rdf: 0 bytes, checksum: d41d8cd98f00b204e9800998ecf8427e (MD5)Approved for entry into archive by Luciana Ferreira (lucgeral@gmail.com) on 2019-09-26T12:35:32Z (GMT) No. of bitstreams: 2 Dissertação - Pedro Henrique Machado Godoy - 2019.pdf: 3208046 bytes, checksum: e124c90ecb9122aab193fbfefddfd9dd (MD5) license_rdf: 0 bytes, checksum: d41d8cd98f00b204e9800998ecf8427e (MD5)Made available in DSpace on 2019-09-26T12:35:32Z (GMT). No. of bitstreams: 2 Dissertação - Pedro Henrique Machado Godoy - 2019.pdf: 3208046 bytes, checksum: e124c90ecb9122aab193fbfefddfd9dd (MD5) license_rdf: 0 bytes, checksum: d41d8cd98f00b204e9800998ecf8427e (MD5) Previous issue date: 2019-08-27Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESapplication/pdfporUniversidade Federal de GoiásPrograma de Pós-graduação em Engenharia Química (IQ)UFGBrasilInstituto de Química - IQ (RG)http://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessReações de acoplamento orgânicoReação de StilleCatálise heterogêneaImpregnação por excesso de solventeOrganic coupling reactionsStille reactionCatalysis heterogeneousExcess solvent impregnationENGENHARIAS::ENGENHARIA QUIMICASistemas catalíticos heterogêneos para reações de acoplamento Stille-MigitaHeterogeneous catalytic systems for Stille-Migita coupling reactionsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesis34814965011584600786006006006007826066743741197278-18486402610968708782075167498588264571reponame:Repositório Institucional da UFGinstname:Universidade Federal de Goiás (UFG)instacron:UFGLICENSElicense.txtlicense.txttext/plain; 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dc.title.eng.fl_str_mv |
Sistemas catalíticos heterogêneos para reações de acoplamento Stille-Migita |
dc.title.alternative.eng.fl_str_mv |
Heterogeneous catalytic systems for Stille-Migita coupling reactions |
title |
Sistemas catalíticos heterogêneos para reações de acoplamento Stille-Migita |
spellingShingle |
Sistemas catalíticos heterogêneos para reações de acoplamento Stille-Migita Godoy, Pedro Henrique Machado Reações de acoplamento orgânico Reação de Stille Catálise heterogênea Impregnação por excesso de solvente Organic coupling reactions Stille reaction Catalysis heterogeneous Excess solvent impregnation ENGENHARIAS::ENGENHARIA QUIMICA |
title_short |
Sistemas catalíticos heterogêneos para reações de acoplamento Stille-Migita |
title_full |
Sistemas catalíticos heterogêneos para reações de acoplamento Stille-Migita |
title_fullStr |
Sistemas catalíticos heterogêneos para reações de acoplamento Stille-Migita |
title_full_unstemmed |
Sistemas catalíticos heterogêneos para reações de acoplamento Stille-Migita |
title_sort |
Sistemas catalíticos heterogêneos para reações de acoplamento Stille-Migita |
author |
Godoy, Pedro Henrique Machado |
author_facet |
Godoy, Pedro Henrique Machado |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Alonso, Christian Gonçalves |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/7285754665946583 |
dc.contributor.advisor-co1.fl_str_mv |
Oliveira, Guilherme Roberto de |
dc.contributor.advisor-co1Lattes.fl_str_mv |
http://lattes.cnpq.br/8239498431579015 |
dc.contributor.referee1.fl_str_mv |
Alonso, Christian Gonçalves |
dc.contributor.referee2.fl_str_mv |
Ostroski, Indianara Conceição |
dc.contributor.referee3.fl_str_mv |
Chagas, Rafael Pavão das |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/5848031195446622 |
dc.contributor.author.fl_str_mv |
Godoy, Pedro Henrique Machado |
contributor_str_mv |
Alonso, Christian Gonçalves Oliveira, Guilherme Roberto de Alonso, Christian Gonçalves Ostroski, Indianara Conceição Chagas, Rafael Pavão das |
dc.subject.por.fl_str_mv |
Reações de acoplamento orgânico Reação de Stille Catálise heterogênea Impregnação por excesso de solvente |
topic |
Reações de acoplamento orgânico Reação de Stille Catálise heterogênea Impregnação por excesso de solvente Organic coupling reactions Stille reaction Catalysis heterogeneous Excess solvent impregnation ENGENHARIAS::ENGENHARIA QUIMICA |
dc.subject.eng.fl_str_mv |
Organic coupling reactions Stille reaction Catalysis heterogeneous Excess solvent impregnation |
dc.subject.cnpq.fl_str_mv |
ENGENHARIAS::ENGENHARIA QUIMICA |
description |
Carbon-carbon coupling reactions are of fundamental importance in the synthesis of organic compounds. The Stille-Migita reaction is a cross-coupling reaction and occurs when an organotin compound and an organic halide hybridized to sp3 react under the presence of a metal-based catalyst, generally palladium. The reaction has the advantage of being compatible with virtually any functional group and for forming products with complex chains, such as pharmaceuticals and agrochemicals. However, Stille synthesis is usually performed by homogeneous catalysis, which enhances the need for costly purification processes necessary to remove metal debris from the reaction products. Thus, this work synthesized and verified the use of heterogeneous catalysts for Stille coupling reactions, using the efficient and economical method of wet impregnation in its preparation by producing monometallic catalysts with different oxides as support. The catalysts were characterized before and after calcination by thermogravimetry and differential thermal analysis (TG / DTA), X-ray diffraction (XRD), Scanning Electron Microscopy (SEM), textural analysis by adsorption/desorption isotherms of N2 and X-ray fluorescence (XRF). The reaction parameters were optimized: time, temperature, type of solvent and catalyst composition. The materials La2O3/Pd and TiO2/Pd showed no catalytic activity, whereas the catalysts Nb2O5/Pd and SiO2/Pd showed good conversions, above 80%. The recycling tests showed considerable loss of activity, which could be associated with filtration and leaching of the active phase between cycles. Nb2O5/Pd showed higher efficiency in the presence of non-toxic solvents (water/ethanol), unusual in Stille reactions. It is expected that this work will contribute to the development of heterogeneous catalysis, particularly in the coupling reactions, since economical methods of synthesis have produced catalytically active materials. |
publishDate |
2019 |
dc.date.accessioned.fl_str_mv |
2019-09-26T12:35:32Z |
dc.date.issued.fl_str_mv |
2019-08-27 |
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.citation.fl_str_mv |
GODOY, P. H. M. Sistemas catalíticos heterogêneos para reações de acoplamento Stille-Migita. 2019. 132 f. Dissertação (Mestrado em Engenharia Química) - Universidade Federal de Goiás, Goiânia, 2019. |
dc.identifier.uri.fl_str_mv |
http://repositorio.bc.ufg.br/tede/handle/tede/10047 |
identifier_str_mv |
GODOY, P. H. M. Sistemas catalíticos heterogêneos para reações de acoplamento Stille-Migita. 2019. 132 f. Dissertação (Mestrado em Engenharia Química) - Universidade Federal de Goiás, Goiânia, 2019. |
url |
http://repositorio.bc.ufg.br/tede/handle/tede/10047 |
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por |
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por |
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3481496501158460078 |
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600 600 600 600 |
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7826066743741197278 |
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-1848640261096870878 |
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2075167498588264571 |
dc.rights.driver.fl_str_mv |
http://creativecommons.org/licenses/by-nc-nd/4.0/ info:eu-repo/semantics/openAccess |
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http://creativecommons.org/licenses/by-nc-nd/4.0/ |
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openAccess |
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Universidade Federal de Goiás |
dc.publisher.program.fl_str_mv |
Programa de Pós-graduação em Engenharia Química (IQ) |
dc.publisher.initials.fl_str_mv |
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 |
dc.source.none.fl_str_mv |
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UFG |
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tasesdissertacoes.bc@ufg.br |
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