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Catalytic Distillation Catalytic Distillation: Modeling and Process Development for Fuels and Chemicals by Aashish Gaurav A thesis presented to the University of Waterloo in fulfillment of the thesis requirement for the degree of Doctor of Philosophy in Chemical Engineering Waterloo, Ontario, Canada, 2017 ©Aashish Gaurav 2017 Examining Committee Membership The following served on the Examining Committee for this thesis. The decision of the Examining Committee is by majority vote. External Examiner Professor Krishnaswamy Nandakumar, Cain Endowed Chair & Professor, Cain Department of Chemical Engineering, Louisiana State University Supervisor(s) Professor Flora Ng, University Professor, Department of Chemical Engineering, University of Waterloo. Internal Member Professor Eric Croiset, Chair and Professor, Department of Chemical Engineering, University of Waterloo. Internal Member Professor Ali Elkamel, Professor, Department of Chemical Engineering, University of Waterloo. Internal-external Member Professor Gordon Savage Professor, Systems Design Engineering, University of Waterloo Other Member(s) Professor Peter Douglas Professor, Department of Chemical Engineering, University of Waterloo ii AUTHOR'S DECLARATION I hereby declare that I am the sole author of this thesis. This is a true copy of the thesis, including any required final revisions, as accepted by my examiners. I understand that my thesis may be made electronically available to the public iii Abstract Catalytic Distillation (CD) is a hybrid green reactor technology that utilizes the dynamics of simultaneous reaction and separation in a single process unit to achieve a more compact, economical, efficient and optimized process design when compared to the traditional multi-unit designs. This thesis advances CD as a process intensification technique by presenting process design and outlining key process conditions for improving the productivity, profitability and environmental impacts of 4 chemical systems: 1) Olefin Oligomerization of isobutene to isooctane 2) Aldol condensation of acetone to MIBK 3) Hydrogenation of benzene to cyclohexane 4) Biodiesel production from soybean oil and yellow grease For optimizing process design or operation over a wide design space and at low cost, a high-fidelity model of the plant or process that is predictive over the entire range of interest is essential. Such a model could be used to optimize design or operation, exploring a wide design space rapidly and at low cost, and applying optimization techniques to determine answers. The thesis develops the first model to describe fast reactions involving a non-condensable gas such as hydrogen in a catalytic distillation process. A reaction with a Hatta number greater than one (Hatta number corresponds to the relative rate of the reaction in a liquid film to the rate of diffusion through the film) is considered to be a fast reaction. The postulate is that a hydrogenation reaction in the solid/liquid film enhances mass transfer leading to improved process performance. A reaction accelerated by “enhanced H2 concentration “via diffusion/reaction could account for the lower hydrogenation partial pressure observed in various CD systems. Hydrogenation is a reaction of immense industrial importance, particularly in the petroleum industry and the current distillation models do not include non-condensable gases. Hydrogenation at lower pressures, is a key CD process advantage reported in patent literature but a scientific study elucidating the observed phenomena was absent from literature. A new proposed film model was developed by incorporating the concept of H2 diffusion through a film in the solid /liquid interface in a three-phase non-equilibrium model developed previously in our laboratory. This film model was validated using three hydrogenation reactions that have been reported to have hydrogenations in lower hydrogen pressure, namely, the hydrogenation of benzene, the CD process for the production of isooctane via the dimerization of isooctane and the iv subsequent hydrogenation of isooctene to isooctane, and the production of methyl-isobutyl- ketone from acetone and hydrogen . In recent years, there has been interest to develop efficient processes for the production of biodiesel from low grade or waste oils with high free fatty acid content. An integrated catalytic distillation process design for continuous large scale biodiesel production from a feedstock with high free fatty acid and a solid acid catalyst was developed using ASPEN PLUS. Model predictions indicated that for an annual biodiesel production of 10 million gallons from vegetable oil, a CD process can result in significant savings in capital (41.4% lesser cost than the conventional process) and utility requirements (18.1% less than the conventional process). The cost of biodiesel was found to highly depend on the feedstock price and hence, in second part of the studies, a new green process for biodiesel production from yellow grease using CD technology was designed. The CD technology was found to lower capital costs by 22.2 % and utility costs by 32.3 %. The CD process also resulted in an improved catalysis, emission control and waste minimization. v Acknowledgements Firstly, I would like to thank my supervisor, Professor Flora Ng for her guidance and support throughout my academic program. I am enamored and grateful for the trust, confidence opportunities she has given me to learn and experience new aspects of research, your valuable and thoughtful counsel, and for your undaunted tenacity in tackling challenging research problems. I am indebted to Professor Rempel, who has been a huge influence on my development as a researcher. His course on research topics in chemical kinetics, catalysis and advanced reactor engineering gave me the opportunity to approach the research from a different angle. I appreciate greatly his encouragement and guidance throughout my research and his effort in proof-reading several of my papers and providing valuable insight to different research elements. To my advisory committee members, I wish to express my sincere thanks and admired gratitude for their valuable suggestions on my research proposal. In particular, I wish to thank Professor Krishnaswamy Nandakumar for his valuable suggestions and Professor Ali Elkamel for his instruction in courses related to numerical methods and optimization that were instrumental in shaping the modeling work presented in this thesis. Chau Mai Thi Quynh, Stephan Dumas and Lu Dong were very helpful in conducting the experiments from which kinetic data has been extracted for the biodiesel simulation studies. Thank You for our patience and hard work. Dr. Behnam Goortani and Pieter Schmal deserve special thanks for helping me to unlock the mysteries of gPROMS. My thanks to Judy Caron, Cathy Logan Dickie and Liz Bevan for help on administrative matters and Dennis Herman and Ravindra Singh for help on technical problems. Financial support from the Natural Sciences and Engineering Research Council of Canada (NSERC) for this research is gratefully acknowledged. I would like to thank the Ontario Government and University of Waterloo for a Trillium scholarship for Graduate Studies. My stay in Waterloo was a unique opportunity and experience, which would not have been so joyful without my friends in University and my hockey and baseball teams. And finally, thank you to my family for your love, patience, support and encouragement. vi Dedication This Thesis is dedicated to my Dad, Ashok Prasad who has been my role-model for hard work, persistence and personal sacrifices, and who instilled in me the inspiration to set high goals and the confidence to achieve them. Time and again, when I have needed help, he has given me his all. I might have had some hardships but my hardships are nothing against the hardships that my father went through in order to get me to where I started. vii Table of Contents Examining Committee Membership ...................................................................................................... ii AUTHOR'S DECLARATION .............................................................................................................. iii Abstract .................................................................................................................................................. iv Acknowledgements ................................................................................................................................ vi Dedication ............................................................................................................................................ vii List of Figures ........................................................................................................................................ xi List of Tables ...................................................................................................................................... xiii List of Abbreviations (in alphabetical order) ........................................................................................ xv Chapter 1 Introduction ............................................................................................................................ 1 1.1 Catalytic Distillation ........................................................................................................................ 1 1.2 Applications of Catalytic Distillation .............................................................................................. 2 1.3 Background
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