Oxida??o de ?steres met?licos de ?cidos graxos insaturados por ?xido de Ni?bio (v): um estudo da atividade do catalisador

Detalhes bibliográficos
Autor(a) principal: Cecchi, Christian Marcelo Paraguass?
Data de Publicação: 2018
Tipo de documento: Tese
Idioma: por
Título da fonte: Biblioteca Digital de Teses e Dissertações da UFRRJ
Texto Completo: https://tede.ufrrj.br/jspui/handle/jspui/4666
Resumo: Natural fatty acids and their esters are becoming an alternative and promising source as substitutes for reagents in synthetic routes. In unsaturated fatty acids, double bonds are attractive reactive centers for various types of reactions. Among the most relevant processes are those derived from the partial or total oxidation of these double bonds by the use of transition metals as catalysts, which include the epoxidation reaction, and other partial oxidations, which lead to the production of diols, aldehydes and/or ketones, or total oxidation, with the production of carboxylic acids as final products. The catalytic properties of niobium oxide (V) (Nb2O5?CBMM) of different degrees ? amorphous, optical and ultra pure, untreated or heat treated at 400, 500, 700 and 900 ?C ? were studied ? before and after interaction with hydrogen peroxide (H2O2) ?, by UV?Visible in diffuse reflectance mode, Raman and FTIR spectroscopies. The presence of NbO7 and NbO8 systems, which is directly related to the surface reaction sites present in different crystallization states, is characterized by the formation of ?1?hydroperoxide and ?2?peroxo type systems. The activity of the different catalysts obtained from the niobium oxide (V) was investigated using the oxidation of oleate and methyl linoleate in the presence of H2O2, acting as a reaction probe. The reaction was monitored by GC and techniques such as GC?MS and 1H and 13C NMR spectrometry were used to determine the dominant product of the reaction as 9?oxo?nonanoic acid methyl ester and only methyl linoleate was reactive. Based on these results, a reaction mechanism was proposed involving an auto?oxidation process that initially leads to the formation of hydroperoxides, which decompose rapidly via Hock?type rearrangement, leading to the formation of aldehydes, pointing to the ?1?hydroperoxide system as the oxidizing species.
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spelling Ferreira, Jos? Carlos Netto149460177-04http://lattes.cnpq.br/2496613154167269Ferreira, Aur?lio Baird BuarqueCesar?n Sobrinho, Dar?Ferreira, Aur?lio Baird BuarqueRocha, Angela SanchesSilva J?nior, Ant?nio Marques daLachter, Elizabeth RoditiHerbst, Marcelo Hawrylak073997997-33http://lattes.cnpq.br/7274418142986892Cecchi, Christian Marcelo Paraguass?2021-05-21T00:46:59Z2018-08-17CECCHI, Christian Marcelo Paraguass?. Oxida??o de ?steres met?licos de ?cidos graxos insaturados por ?xido de Ni?bio (v): um estudo da atividade do catalisador. 2018. [147 f.]. Tese( Programa de P?s-Gradua??o em Qu?mica) - Universidade Federal Rural do Rio de Janeiro, [Serop?dica - RJ] .https://tede.ufrrj.br/jspui/handle/jspui/4666Natural fatty acids and their esters are becoming an alternative and promising source as substitutes for reagents in synthetic routes. In unsaturated fatty acids, double bonds are attractive reactive centers for various types of reactions. Among the most relevant processes are those derived from the partial or total oxidation of these double bonds by the use of transition metals as catalysts, which include the epoxidation reaction, and other partial oxidations, which lead to the production of diols, aldehydes and/or ketones, or total oxidation, with the production of carboxylic acids as final products. The catalytic properties of niobium oxide (V) (Nb2O5?CBMM) of different degrees ? amorphous, optical and ultra pure, untreated or heat treated at 400, 500, 700 and 900 ?C ? were studied ? before and after interaction with hydrogen peroxide (H2O2) ?, by UV?Visible in diffuse reflectance mode, Raman and FTIR spectroscopies. The presence of NbO7 and NbO8 systems, which is directly related to the surface reaction sites present in different crystallization states, is characterized by the formation of ?1?hydroperoxide and ?2?peroxo type systems. The activity of the different catalysts obtained from the niobium oxide (V) was investigated using the oxidation of oleate and methyl linoleate in the presence of H2O2, acting as a reaction probe. The reaction was monitored by GC and techniques such as GC?MS and 1H and 13C NMR spectrometry were used to determine the dominant product of the reaction as 9?oxo?nonanoic acid methyl ester and only methyl linoleate was reactive. Based on these results, a reaction mechanism was proposed involving an auto?oxidation process that initially leads to the formation of hydroperoxides, which decompose rapidly via Hock?type rearrangement, leading to the formation of aldehydes, pointing to the ?1?hydroperoxide system as the oxidizing species.Os ?cidos graxos naturais e seus ?steres est?o se tornando uma fonte alternativa e promissora como substitutos para reagentes em rotas sint?ticas. Nos ?cidos graxos insaturados as liga??es duplas s?o centros reativos atraentes para v?rios tipos de rea??es. Entre os processos mais relevantes est?o os derivados da oxida??o parcial ou total dessas liga??es duplas pelo uso de metais de transi??o como catalisadores, os quais incluem a rea??o de epoxida??o, e outras oxida??es parciais, que levam ? produ??o de di?is, alde?dos e/ou cetonas, ou oxida??o total, com a produ??o de ?cidos carbox?licos como produtos finais. As propriedades catal?ticas do ?xido de ni?bio (V) (Nb2O5?CBMM) de diferentes graus ? amorfo, ?tico e ultra puro, n?o tratado ou tratado termicamente a 400, 500, 700 e 900 ?C ? foram estudadas ? antes e ap?s de intera??o com per?xido de hidrog?nio (H2O2) ?, por espectroscopias de UV?Vis?vel em modo de reflect?ncia difusa, Raman e FTIR?ATR. Caracterizou?se a presen?a de sistemas do tipo NbO7 e NbO8, que est? diretamente relacionada aos s?tios reacionais superficiais presentes em diferentes estados de cristaliza??o, caracterizados pela forma??o de sitemas do tipo ?1?hidroperoxo e ?2?peroxo. A atividade dos diferentes catalisadores obtidos a partir do ?xido de ni?bio (V) foi investigada utilizando a oxida??o de oleato e do linoleato de metila na presen?a de H2O2, funcionando como sonda reacional. A rea??o foi acompanhada por CG e t?cnicas como CG?EM e espectrometrias de RMN de 1H e 13C foram utilizadas para determinar o produto dominante da rea??o como sendo o ?ster met?lico do ?cido 9?oxo?nonan?ico, sendo reativo somente o linoleato de metila. Com base nesses resultados foi proposto um mecanismo de rea??o envolvendo um processo de auto?oxida??o que leva inicialmente ? forma??o de hidroper?xidos, que se decomp?em rapidamente via rearranjo do tipo Hock, levando ? forma??o de alde?dos, indicando como esp?cie oxidante o sitema ?1?hidroperoxo.Submitted by Sandra Pereira (srpereira@ufrrj.br) on 2021-05-21T00:46:59Z No. of bitstreams: 1 2018 - Christian Marcelo Paraguass? Cecchi.pdf: 5837736 bytes, checksum: 026fa88ea93669d52acc867f6241ab1a (MD5)Made available in DSpace on 2021-05-21T00:46:59Z (GMT). No. of bitstreams: 1 2018 - Christian Marcelo Paraguass? Cecchi.pdf: 5837736 bytes, checksum: 026fa88ea93669d52acc867f6241ab1a (MD5) Previous issue date: 2018-08-17Coordena??o de Aperfei?oamento de Pessoal de N?vel Superior, CAPES, Brasil.application/pdfhttps://tede.ufrrj.br/retrieve/65176/2018%20-%20Christian%20Marcelo%20Paraguass%c3%ba%20Cecchi.pdf.jpgporUniversidade Federal Rural do Rio de JaneiroPrograma de P?s-Gradua??o em Qu?micaUFRRJBrasilInstituto de Ci?ncias Exatas1. Mbaraka, I.K.; Shanks, B.H. J. Am. Oil Chem. Soc. 2006, 83, 79-91, doi:10.1007/s11746-006-1179-x. 2. Biermann, U.; Bornscheuer, U.; Meier, M.A.; Metzger, J.O.; Sch?fer, H.J. Angew. Chem. Int. 2011, 50, 3854-3871, doi:10.1002/anie.201002767. 3. Anneken, D.J.; Both, S.; Christoph, R.; Fieg, G.; Steinberner, U.; Westfechtel, A. Ullmann's Encycl. Ind. 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dc.title.por.fl_str_mv Oxida??o de ?steres met?licos de ?cidos graxos insaturados por ?xido de Ni?bio (v): um estudo da atividade do catalisador
title Oxida??o de ?steres met?licos de ?cidos graxos insaturados por ?xido de Ni?bio (v): um estudo da atividade do catalisador
spellingShingle Oxida??o de ?steres met?licos de ?cidos graxos insaturados por ?xido de Ni?bio (v): um estudo da atividade do catalisador
Cecchi, Christian Marcelo Paraguass?
linoleato de metila
Espectroscopia Raman
oxida??o
methyl linoleate
Raman spectroscopy
oxidation
Qu?mica
title_short Oxida??o de ?steres met?licos de ?cidos graxos insaturados por ?xido de Ni?bio (v): um estudo da atividade do catalisador
title_full Oxida??o de ?steres met?licos de ?cidos graxos insaturados por ?xido de Ni?bio (v): um estudo da atividade do catalisador
title_fullStr Oxida??o de ?steres met?licos de ?cidos graxos insaturados por ?xido de Ni?bio (v): um estudo da atividade do catalisador
title_full_unstemmed Oxida??o de ?steres met?licos de ?cidos graxos insaturados por ?xido de Ni?bio (v): um estudo da atividade do catalisador
title_sort Oxida??o de ?steres met?licos de ?cidos graxos insaturados por ?xido de Ni?bio (v): um estudo da atividade do catalisador
author Cecchi, Christian Marcelo Paraguass?
author_facet Cecchi, Christian Marcelo Paraguass?
author_role author
dc.contributor.advisor1.fl_str_mv Ferreira, Jos? Carlos Netto
dc.contributor.advisor1ID.fl_str_mv 149460177-04
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/2496613154167269
dc.contributor.advisor-co1.fl_str_mv Ferreira, Aur?lio Baird Buarque
dc.contributor.advisor-co2.fl_str_mv Cesar?n Sobrinho, Dar?
dc.contributor.referee1.fl_str_mv Ferreira, Aur?lio Baird Buarque
dc.contributor.referee2.fl_str_mv Rocha, Angela Sanches
dc.contributor.referee3.fl_str_mv Silva J?nior, Ant?nio Marques da
dc.contributor.referee4.fl_str_mv Lachter, Elizabeth Roditi
dc.contributor.referee5.fl_str_mv Herbst, Marcelo Hawrylak
dc.contributor.authorID.fl_str_mv 073997997-33
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/7274418142986892
dc.contributor.author.fl_str_mv Cecchi, Christian Marcelo Paraguass?
contributor_str_mv Ferreira, Jos? Carlos Netto
Ferreira, Aur?lio Baird Buarque
Cesar?n Sobrinho, Dar?
Ferreira, Aur?lio Baird Buarque
Rocha, Angela Sanches
Silva J?nior, Ant?nio Marques da
Lachter, Elizabeth Roditi
Herbst, Marcelo Hawrylak
dc.subject.por.fl_str_mv linoleato de metila
Espectroscopia Raman
oxida??o
topic linoleato de metila
Espectroscopia Raman
oxida??o
methyl linoleate
Raman spectroscopy
oxidation
Qu?mica
dc.subject.eng.fl_str_mv methyl linoleate
Raman spectroscopy
oxidation
dc.subject.cnpq.fl_str_mv Qu?mica
description Natural fatty acids and their esters are becoming an alternative and promising source as substitutes for reagents in synthetic routes. In unsaturated fatty acids, double bonds are attractive reactive centers for various types of reactions. Among the most relevant processes are those derived from the partial or total oxidation of these double bonds by the use of transition metals as catalysts, which include the epoxidation reaction, and other partial oxidations, which lead to the production of diols, aldehydes and/or ketones, or total oxidation, with the production of carboxylic acids as final products. The catalytic properties of niobium oxide (V) (Nb2O5?CBMM) of different degrees ? amorphous, optical and ultra pure, untreated or heat treated at 400, 500, 700 and 900 ?C ? were studied ? before and after interaction with hydrogen peroxide (H2O2) ?, by UV?Visible in diffuse reflectance mode, Raman and FTIR spectroscopies. The presence of NbO7 and NbO8 systems, which is directly related to the surface reaction sites present in different crystallization states, is characterized by the formation of ?1?hydroperoxide and ?2?peroxo type systems. The activity of the different catalysts obtained from the niobium oxide (V) was investigated using the oxidation of oleate and methyl linoleate in the presence of H2O2, acting as a reaction probe. The reaction was monitored by GC and techniques such as GC?MS and 1H and 13C NMR spectrometry were used to determine the dominant product of the reaction as 9?oxo?nonanoic acid methyl ester and only methyl linoleate was reactive. Based on these results, a reaction mechanism was proposed involving an auto?oxidation process that initially leads to the formation of hydroperoxides, which decompose rapidly via Hock?type rearrangement, leading to the formation of aldehydes, pointing to the ?1?hydroperoxide system as the oxidizing species.
publishDate 2018
dc.date.issued.fl_str_mv 2018-08-17
dc.date.accessioned.fl_str_mv 2021-05-21T00:46:59Z
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 CECCHI, Christian Marcelo Paraguass?. Oxida??o de ?steres met?licos de ?cidos graxos insaturados por ?xido de Ni?bio (v): um estudo da atividade do catalisador. 2018. [147 f.]. Tese( Programa de P?s-Gradua??o em Qu?mica) - Universidade Federal Rural do Rio de Janeiro, [Serop?dica - RJ] .
dc.identifier.uri.fl_str_mv https://tede.ufrrj.br/jspui/handle/jspui/4666
identifier_str_mv CECCHI, Christian Marcelo Paraguass?. Oxida??o de ?steres met?licos de ?cidos graxos insaturados por ?xido de Ni?bio (v): um estudo da atividade do catalisador. 2018. [147 f.]. Tese( Programa de P?s-Gradua??o em Qu?mica) - Universidade Federal Rural do Rio de Janeiro, [Serop?dica - RJ] .
url https://tede.ufrrj.br/jspui/handle/jspui/4666
dc.language.iso.fl_str_mv por
language por
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