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N-Butanol/Butyl Acrylate/ Water

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N-Butanol/Butyl Acrylate/ Water Faculdade de Engenharia da Universidade do Porto Process Intensification for Butyl Acrylate Synthesis based on Sorption-Enhanced Reaction and Pervaporation-based Hybrid Processes Dissertation presented to Faculdade de Engenharia da Universidade do Porto for the degree of PhD in Chemical and Biological Engineering by Dânia Sofia Martins Constantino Supervisor: Professor Alírio E. Rodrigues Co-supervisors: Dr. Ana M. Ribeiro and Dr. Rui P. Faria Laboratory of Separation and Reaction Engineering, Associate Laboratory LSRE-LCM Department of Chemical engineering, Faculty of Engineering, University of Porto 2019 FEUP-LSRE/LCM - Universidade do Porto © Dânia Sofia Martins Constantino, 2019 All rights reserved This thesis was financially supported by Project POCI-01-0145-FEDER-006984 – Associate Laboratory LSRE-LCM funded by FEDER through COMPETE2020 Programa Operacional Competitividade e Internacionalização (POCI) – and by national funds through FCT – Fundação para a Ciência e Tecnologia, Associate Laboratory LSRE- LCM - UID/EQU/50020/2019 - funded by national funds through FCT/MCTES (PIDDAC), and Project NORTE-01-0145-FEDER-000006, supported by Norte Portugal Regional Operational Programme (NORTE 2020), under the Portugal 2020 Partnership Agreement, through the European Regional Development Fund (ERDF). Acknowledgements Some people were essential to accomplish this project, so my deepest acknowledgements are for them. First of all, I want to thank to Associate Laboratory of Separation and Reaction Engineering and Catalysis and Materials, namely to its Director, Professora Madalena Dias, for giving me this great opportunity that contributed for my personal and professional grow up, as well as all her availability and support to solve any bureaucratic issue, every time it was required. Now, I would like to express my sincere gratitude to my supervisor, Professor Alírio Rodrigues, for the continuous support, guidance, motivation to do always more and better, and for his immense shared knowledge. His long and successful journey is impressive being an inspiration for all who worked or dealt with him, so I am privileged to be part of his work-team. Then, I would like to thank to my co-supervisors, Dr Ana Mafalda Ribeiro and Dr Rui Pedro Faria, for all the support, guidance, friendship and availability for productive discussions about the main challenges that were emerging during this project, which were an asset to make important decisions when required. Their knowledge and abilities were crucial along this journey. Thank you for all comments and advices. I cannot forget that I had the pleasure to start this project with Dr Carla Pereira, who impressed me by her great abilities and the way she faces each challenge. I am very grateful for her advices, motivation and friendship and I wish her the best of luck, mainly at this stage of her life. I am deeply thankful to my dear friends, namely, Filipa, Vanessa, Raquel, Manuela and Mariana (the girl’s team of the twelve o’clock), with whom I shared doubts, fears and laughs. Thank you girls for your patience and for your friendship. My last acknowledgements, but not less important, go to my parents, by their dedication and patience, my brother, Luis Constantino and my husband, Wesley Souza, for all the emotional support and, finally, to the love of my life, my son, Santiago, who challenges me every day to be a better person. “New ways of thinking—an integrated multidimensional approach to the problems of global sustainability—have long been needed, and it is up to us to decide whether the especially difficult challenges that we are facing today will jolt us into finding and accepting them.” by Peter H. Raven Former president of the American Association for the Advancement of Science, 2002. Resumo A síntese de acrilato de butilo obtido através da esterificação do ácido acrílico e do n- butanol apresenta algumas limitações devido ao equilíbrio da reação e sobretudo à complexidade termodinâmica do sistema. Para além disso, existe um elevado risco de polimerização do ácido acrílico e do acrilato de butilo quando submetidos a elevadas temperaturas. Estas limitações fazem deste sistema um tema muito desafiante entre a comunidade científica no sentido de encontrar um processo capaz de ultrapassar estes inconvenientes, melhorando o processo convencional em termos ambientais e económicos. Nesse sentido, o objetivo deste trabalho consistiu no estudo de diferentes estratégias de intensificação de processos para a síntese de acrilato de butilo com base na integração do processo de reação e separação numa só unidade por forma a ultrapassar a conversão de equilíbrio por remoção contínua da água (subproduto) recorrendo a técnicas cromatográficas (adsorção) e de pervaporação. Deste modo, as diferentes estratégias adotadas nesta investigação contemplaram: reatores cromatográficos de leito fixo, reatores cromatográficos de leito fixo com membranas integradas e, numa fase posterior, processos cíclicos de adsorção/ pervaporação, nomeadamente reatores cromatográficos de leito móvel simulado. Em todos os casos optou-se por usar a mesma fase estacionária, a resina de permuta iónica Amberlyst-15, de modo a facilitar a comparação dos diferentes processos estudados. Assim, numa primeira fase, foram realizados experimentalmente estudos dinâmicos de adsorção e pervaporação, na ausência de reação, a fim de estimar os respetivos parâmetros de cada componente e de forma a ser possível prever e comparar o desempenho dos reatores de leito fixo e de leito fixo com membranas hidrofílicas integradas. Para isso, modelos matemáticos foram desenvolvidos para cada tecnologia, considerando fenómenos de transferência de massa, reação, adsorção e pervaporação, os quais foram posteriormente estendidos para implementação de tecnologias de processos cíclicos, como o reator de leito móvel simulado e o reator de membranas de leito móvel simulado. Os modelos matemáticos previamente desenvolvidos permitiram o estudo da otimização dos respetivos processos abordados neste trabalho e o dimensionamento dos mesmos à escala industrial. A síntese experimental de acrilato de butilo foi também realizada no reator de leito móvel simulado à escala piloto disponível no laboratório (LICOSEP), variando alguns parâmetros de operação no sentido de validar o modelo matemático previamente desenvolvido no qual foram usados os parâmetros de adsorção multicomponente previamente determinados numa unidade de leito fixo na ausência de reação. Numa fase final, foi realizada uma breve análise aos fatores energéticos e económicos envolvidos nos diferentes processos cíclicos à escala industrial de forma a avaliar a viabilidade e competitividade das estratégias de intensificação do processo propostas neste trabalho para a síntese de acrilato de butilo comparativamente aos diferentes processos apresentados na literatura. Abstract The butyl acrylate synthesis obtained from the esterification reaction between acrylic acid and n-butanol presents some limitations due to the reaction equilibrium and mainly due to the thermodynamic complex behaviour of the system. Furthermore, there is a high risk of polymerisation of acrylic acid and butyl acrylate when they are submitted to high temperatures. All these limitations make this system a very challenging subject among the scientific community towards finding a process that is able to overcome these drawbacks improving the conventional process regarding economic and environmental issues. The main objective of this work was to study different process intensification strategies for the butyl acrylate synthesis based on the integration of reaction and separation in a single unit in order to overcome the equilibrium conversion by the continuous removal of water (by-product) using chromatographic (adsorption) and pervaporation techniques. Thus, the different strategies adopted in this research involved: fixed-bed chromatographic reactors, fixed-bed chromatographic reactors with integrated membranes and, at a later stage, cyclic adsorption/ pervaporation processes, namely simulated moving bed chromatographic reactors. In all cases, the same stationary phase was used, the Amberlyst-15 ion exchange resin, in order to perform a fair comparison between the different studied processes. Thus, in a first stage, dynamic studies of adsorption and pervaporation were accomplished, in the absence of reaction, in order to estimate the respective parameters for each compound and to enable the prediction and comparison of the performance between the fixed-bed adsorptive reactor and the fixed-bed adsorptive reactor with integrated hydrophilic membranes. For that, mathematical models were developed for each technology, considering phenomena like mass transfer, reaction, adsorption and pervaporation, which were then extended to model the other continuous processes, such as the simulated moving bed reactor and the simulating moving bed membrane reactor. The mathematical models previously defined allowed to study the optimisation of the processes addressed in this work and to perform the respective scaling up to industrial scale. The experimental butyl acrylate synthesis was also carried out in the simulate moving bed reactor pilot scale unit (LICOSEP) available in the laboratory, by changing some operating parameters in order to validate the mathematical model developed earlier using the multicomponent adsorption equilibrium parameters previously determined in a fixed- bed unit in absence of reaction. Finally, a brief analysis to the energetic and
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