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Applications of Ionic Liquids in Membrane Separation

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Applications of Ionic Liquids in Membrane Separation University of Arkansas, Fayetteville ScholarWorks@UARK Theses and Dissertations 12-2019 Applications of Ionic Liquids in Membrane Separation Mohanad Kamaz University of Arkansas, Fayetteville Follow this and additional works at: https://scholarworks.uark.edu/etd Part of the Complex Fluids Commons, Membrane Science Commons, and the Transport Phenomena Commons Citation Kamaz, M. (2019). Applications of Ionic Liquids in Membrane Separation. Theses and Dissertations Retrieved from https://scholarworks.uark.edu/etd/3491 This Dissertation is brought to you for free and open access by ScholarWorks@UARK. It has been accepted for inclusion in Theses and Dissertations by an authorized administrator of ScholarWorks@UARK. For more information, please contact [email protected]. Applications of Ionic Liquids in Membrane Separation A dissertation submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in Engineering by Mohanad Kamaz University of Basrah Bachelor of Science in Chemical Engineering, 2011 University of Arkansas Master of Science in Chemical Engineering, 2017 December 2019 University of Arkansas This dissertation is approved for recommendation to the Graduate Council. ____________________________________ Ranil Wickramasinghe, Ph.D. Dissertation Director ____________________________________ ____________________________________ David Ford, Ph.D. Ed Clauson, Ph.D. Committee Member Committee Member ____________________________________ ____________________________________ Xianghong Qian, Ph.D. Wen Zhang, Ph.D. Committee Member Committee Member Abstract Ionic liquids represent an emerging attractive material in membrane technology. The central theme of this doctoral dissertation is to develope novel membranes using ionic liquids. Two different approaches were used to prepare ionic liquid membranes including the immobilization of ionic liquid within the membrane pores or the use of pressure assembly method to deposit a selective ionic liquid layer on the top membrane surface. In chapter 2, imidazolium ionic liquids with three different alkyl halides were successfully synthesized and used to prepare supported ionic liquid membranes (SILMs). SILMs preraper were tested for aqueous and nonaqueous applications. For nonaqueous applications, the trend of separation was found to be divinylbenzene> styrene> toluene, which was attributed to the extended conjugation of π electron cloud. For nonaqueous system, preferential separation of different dyes was achieved. In chapter 3, SILMs have been tested for the fractionation of organic compounds. Fractionation of a feed stream consisting of benzene, naphthalene, and phenanthrene in tetradecane and cis- and trans-stilbene in hexane were investigated. Differences in the π electron cloud density of the aromatic solutes influence their interactions with the imidazolium cation which can affect the rates of transport. In the case of the three aromatic solutes the degree of conjugation and molecular weight increase in the order of benzene, naphthalene, and phenanthrene. However, for cis-and trans-stilbene, the mass transfer coefficient was larger for all three ionic liquids. Aqueous SILM was used as the liquid membrane phase to fractionate two nucleobases: thymine and cytosine in water. The mass transfer coefficient for thymine was 5.5 times greater than cytosine indicating the possibility of exploiting multimodal interactions fractionate compounds. Chapter 4 constitutes the preparation of novel polyionic liquid augmented membranes that were fabricated using pressure assisted self-assembly and employed for π- electron cloud mediated separation of aromatics from their aliphatic homologs. The prepared membranes can be employed for the fractionation of aromatics such as benzene, toluene, p-xylene, nitrobenzene. Further, these augmented membranes were demonstrated to have preferential separation of one stereoisomer over others. Finally, chapter 5 includes conclusions drawn out of this research and future directions and recommendations. Dedication To my beloved greatest mother, Azhar Almosowy. To my father, whose soul is always present to support me throughout my journeys, Ali Kamaz. Acknowledgment First and foremost, I would like to express my sincere gratitude to my supervisor Dr. Ranil Wickramasinghe for giving me the opportunity to this journey and fund me throughout this Ph.D. study as well as introducing me to the membrane research. His significant scientific contribution and wise guidance made this Ph.D. research not impossible. Also, I would show my appreciation and gratitude to Dr. Arijit Sengupta for all the innovative input he had put in the research and the long pertaining discussion and explanations. His guidance and sharp notifications made this research recognizable. My thanks also go to all the group members who helped me in my research and kept standing me on my feet during the hard times. Financial support from the Arkansas Research Alliance and the University of Arkansas are gratefully acknowledged. I would also like to express my great appreciation for my family in particular my mother. I am so thankful for your unconditional love and support that motivates me to do the best. Thanks for all the prayers you said to keep me blessed. Besides my advisor, I would like to thank my dissertation committee: Prof. David Ford, Prof. Ed Clauson, Prof. Xianghong Qian and Associate Prof. Wen Zhang. Thanks for being part of this dissertation and giving time to attend my defense. Also, thanks for your constructive comments and suggestions which widen and strengthen my research from many perspectives. Last but not the least, I would like to thank my host family the Petersons here in the U.S. for their tremendous unconditional love and support, especially taking care of me during the downtimes and keeping me moving forward. Mohanad Kamaz Ralph E Martin Department of Chemical Engineering University of Arkansas Table of Contents Chapter 1 Introduction ............................................................................................................. 1 1.1 Membrane Based Technology ........................................................................................... 1 1.2 Membrane processes ......................................................................................................... 1 1.3 Advanced membrane separation ........................................................................................ 4 1.4 Novel mechanisms in membrane separation ...................................................................... 5 1.4.1 Charge based separation mechanism ........................................................................... 6 1.4.2 Hydrophobic interactions ............................................................................................ 8 1.4.3 Facilitated transport .................................................................................................... 9 1.4.4 Pi electron cloud interaction ..................................................................................... 11 1.5 Ionic liquids and poly(ionic liquids) ................................................................................ 14 1.5.1 Synthesis of ionic liquids .......................................................................................... 18 1.6 Preparation of IL based membranes ................................................................................. 20 1.6.1 Supported ionic liquid membranes ............................................................................ 21 1.6.2 Physical coating using pressure assisted self-assembly ............................................. 22 1.7 Application of IL membranes .......................................................................................... 24 1.8 References....................................................................................................................... 30 Chapter 2 Pi electron cloud mediated separation of aromatics using supported ionic liquid membranes (SILMs) having antibacterial activity ................................................................ 38 2.1 Introduction ................................................................................................................ 39 2.2 Experimental ................................................................................................................... 41 2.2.1 Materials .................................................................................................................. 41 2.2.2 Synthesis of ionic liquid ........................................................................................... 41 2.2.3 Preparation of supported liquid membranes .............................................................. 43 2.2.4 Characterization ....................................................................................................... 43 2.2.5 Transport studies ...................................................................................................... 44 2.2.6 Stability of the SIL membranes ................................................................................. 45 2.3 Results and discussion ..................................................................................................... 45 2.3.1 Characterization ....................................................................................................... 45 2.3.2 Pi- electron mediated separation of aromatics and dyes ............................................. 47 2.3.3
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