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Heterogeneização De Complexos À Base De Ródio Com Ligan Tes Ciclopentadienila: Estudo Em Reações De Hidrogenação Catalítica”

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Heterogeneização De Complexos À Base De Ródio Com Ligan Tes Ciclopentadienila: Estudo Em Reações De Hidrogenação Catalítica” UNIVERSIDADE FEDERAL DO RIO GRANDE DO SUL INSTITUTO DE QUÍMICA PROGRAMA DE PÓS-GRADUAÇÃO EM QUÍMICA “HETEROGENEIZAÇÃO DE COMPLEXOS À BASE DE RÓDIO COM LIGAN TES CICLOPENTADIENILA: ESTUDO EM REAÇÕES DE HIDROGENAÇÃO CATALÍTICA” Fernanda Rosi Soares Pederzolli Tese apresentada como requisito parcial para a obtenção do grau de Doutor em Química Prof. Dr. Ricardo Gomes da Rosa Orientador Profa Dra Silvana Inês Wolke Co-orientadora Porto Alegre, julho de 2018. A presente tese foi realizada inteiramente pelo autor, exceto as colaborações as quais serão devidamente citadas nos agradecimentos, no período entre março/2012 e junho/2018, no Instituto de Química da Universidade Federal do Rio Grande do Sul sob Orientação do Professor Doutor Ricardo Gomes da Rosa e Co-orientação da Professora Doutora Silvana Inês Wolke. A tese foi julgada adequada para a obtenção do título de Doutor em Química pela seguinte banca examinadora: Comissão Examinadora: Prof. Dr. Jones Limberger - PUCRIO Prof. Dr. Leandro Bresolin - FURG Prof. Dr. João Henrique Zimnoch dos Prof. Dr. José Ribeiro Gregório – Santos – PPGQ /UFRGS PPGQ /UFRGS Prof. Dr. Ricardo Gomes da Rosa Profa Dra Silvana Inês Wolke (Orientador) (Co-orientadora) Fernanda Rosi Soares Pederzolli (Aluna) Agradecimentos Aos Professores Ricardo Gomes da Rosa e Silvana I. Wolke pela orientação, incentivo e paciência. Aos Profesores membros da banca examinadora da Tese: Jones Limberger, Leandro Bresolin, João Henrique Zimnoch dos Santos e José Ribeiro Gregório por gentilmente aceitarem o convite. Aos colegas de laboratório Henrique, Maria Francisca, Nathália, Felipe, Douglas, Karine, Bárbara, Bruno e Larissa pela amizade. Ao Professor Jairton Dupont pelo fornecimento de D2 e acesso a suas dependências laboratoriais. Ao CME-UFRGS pelas análises de microscopia de transmissão eletrônica e microscopia eletrônica de varredura de alta resolução e espectroscopia de energia dispersiva. Ao CNANO pelas análises de ressonância magnética nuclear no estado sólido. À Fundação de Amparo à Pesquisa do Estado do Rio Grande do Sul (FAPERGS) pelo financiamento do projeto PRONEX/FAPERGS- CNPq, 16/2551/0000. Ao CAPES pela bolsa concedida. Ao Instituto de Química da UFRGS. À minha Família, em especial aos meus pais Claudio e Telma pela compreensão e apoio incondicional. Às minhas amigas Kelly e Grazieli pela paciência, conselhos e amizade. ii Lista de trabalhos gerados a partir dos resultados descritos na tese Artigos publicados durante o período de doutoramento F.R.S. Pederzolli, S.I. Wolke, R. G. da Rosa, Recyclable rhodium-Cp’-heterogenized catalysts for hydrogenation of olefins, J. Catal. 360 (2018) 201–212. doi:10.1016/j.jcat.2018.02.007. Trabalhos publicados em congressos F.R.S. Pederzolli, R.G da Rosa, S.I. Wolke, Funcionalização de sílicas com 3- ciclopentadienil-proopiltrietoxissilano para heterogeneização de catalisadores [Rh-Cp]. No 17º. Congresso Brasileiro de Catálise e VII Congresso de Catálise do Mercosul, em Gramado de 15 a 19 de setembro de 2013. F.R.S. Pederzolli, S.I. Wolke, R.G. da Rosa, "Hidrogenação de olefinas por complexos de ródio com ligante ciclopentadienila-alcoxissilano". Na 38ª. Reunião Anual da Sociedade Brasileira de Química, em Águas de Lindóia, 28 de maio de 2015. iii Sumário Lista de figuras .............................................................................................................. ix Lista de tabelas ............................................................................................................ xiv Lista de abreviaturas e símbolos ................................................................................. xv Resumo........................................................................................................................xviii Abstract.........................................................................................................................xix 1. Introdução ................................................................................................................ 1 Objetivos ............................................................................................................ 3 2. Revisão bibliográfica ............................................................................................... 4 Heterogeneização de precursores catalíticos em sílica ...................................... 4 2.1.1. Heterogeneização por reação direta dos complexos com a superfície da sílica............ ............................................................................................................... 4 2.1.2. Heterogeneização de complexos em sílicas funcionalizadas ...................... 6 2.1.3. Heterogeneização de complexos com ligantes funcionalizados em sílica............ ............................................................................................................. 12 2.1.4. Heterogeneização de precursores catalíticos pelo método sol-gel ............ 23 2.1.4.1. Heterogeneização de precursores catalíticos por condensação com TMOS/TEOS ....................................................................................................... 24 2.1.4.2. Imobilização de Precursores Catalíticos por encapsulamento em Sílica Sol-gel.................... .............................................................................................. 25 2.1.5. Heterogeneização de precursores catalíticos em materiais híbridos a base de sílicio....... ................................................................................................................. 26 Sistemas Rh-Cp em que ocorre a mudança de hapticidade de 5 para 4 ....... 28 Considerações finais ........................................................................................ 31 3. Parte experimental ................................................................................................ 32 Materiais .......................................................................................................... 32 Métodos de análise ........................................................................................... 32 3.2.1. Espectroscopia no Infravermelho .............................................................. 32 3.2.2. Espectroscopia de Ressonância Magnética Nuclear .................................. 33 3.2.3. Microscopia Eletrônica de Transmissão (MET) ........................................ 33 3.2.4. Microscopia Eletrônica de Varredura de Alta Resolução e Espectroscopia de Energia Dispersiva (MEV-FEG-EDS) ................................................................ 33 3.2.5. Isotermas de adsorção-dessorção de nitrogênio ........................................ 34 3.2.6. Cromatografia em fase gasosa ................................................................... 34 3.2.7. Espectrometria de massas .......................................................................... 34 Sínteses ............................................................................................................ 35 iv 3.3.1. Sínteses dos Alcoxissilanos ....................................................................... 35 3.3.1.1. Síntese do 3-iodopropiltrietoxissilano ............................................... 35 3.3.1.2. Síntese do trietoxi(3-(2,3,4,5-tetrametilciclopenta-2,4-dien-1- il)propil)silano (Cp’).............................................................................................36 3.3.1.3. Síntese do trietoxi(3-(ciclopenta-2,4-dien-1-il)propil)silano (Cp) .... 37 3.3.2. Síntese dos precursores catalíticos ............................................................ 38 3.3.2.1. Síntese do precursor Rh-Cp’ ............................................................. 38 3.3.2.2. Síntese do precursor [Rh-Cp’]PF6 ..................................................... 39 3.3.3. Imobilização dos precursores em sílica ..................................................... 39 3.3.3.1. Imobilização do precursor Rh-Cp’ em sílica Aerosil 200- Rota A (Rh- Cp’ /Aerosil 200) ................................................................................................. 39 3.3.3.2. Imobilização do precursor Rh-Cp’ em sílica sol-gel – Rota B (Rh-Cp’ /Sol-gel)............... ................................................................................................ 40 3.3.3.3. Imobilização [Rh-Cp’] PF6 em sílica sol-gel .................................... 40 3.3.4. Funcionalização de sílicas com ligante ciclopentadienila ......................... 41 3.3.4.1. Funcionalização da sílica Aerosil 200 com 3-cloropropiltrietoxissilano – Rota C................... ............................................................................................ 41 3.3.4.2. Modificação da sílica Aerosil 200 funcionalizada com 3- cloropropiltrietoxissilano – Rota C ..................................................................... 42 3.3.4.3. Funcionalização da sílica Aerosil 200 com o Cp – Rota D ............... 42 3.3.4.4. Síntese da sílica sol-gel com o 3-cloropropiltrietoxissilano – Rota E................. ....................................................................................................... ...43 3.3.4.5. Síntese da sílica sol-gel Cp – Rota E ................................................ 43 3.3.4.6. Síntese da sílica sol-gel Cp’ – Rota F ............................................... 44 Testes catalíticos em hidrogenação de olefinas e dienos ................................. 44 Deuteração ....................................................................................................... 45 4. Resultados
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