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High-Pressure Phase Equilibria of Ionic Liquids and Compressed

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High-Pressure Phase Equilibria of Ionic Liquids and Compressed High-Pressure Phase Equilibria of Ionic Liquids and Compressed Gases for Applications in Reactions and Absorption Refrigeration by Wei Ren Submitted to the graduate degree program in Chemical and Petroleum Engineering and the Graduate Faculty of the University of Kansas in partial fulfillment of the requirements for the degree of Doctor of Philosophy Committee Members: ________________________ Chairperson* Aaron M. Scurto ________________________ Kyle V.Camarda ________________________ Laurence R. Weatherley ________________________ Jyun-Syung Tsau ________________________ Brian B. Laird Date defended: 11/23/2009 The Dissertation Committee for Wei Ren certifies that this is the approved version of the following dissertation: High-Pressure Phase Equilibria of Ionic Liquids and Compressed Gases for Applications in Reactions and Absorption Refrigeration Wei Ren Committee Members: ________________________ Chairperson* Aaron M. Scurto ________________________ Kyle V. Camarda ________________________ Laurence R. Weatherley ________________________ Jyun-Syung Tsau ________________________ Brian B. Laird Date approved: ____________ i Abstract High-Pressure Phase Equilibria of Ionic Liquids and Compressed Gases for Applications in Reactions and Absorption Refrigeration by Wei Ren Environmental concerns using volatile organic compounds have attracted intensive research of replacing them with more sustainable (“greener”) solvents. Ionic liquids have been promising alternatives due to their unique physical and chemical properties, especially their lack of volatility. However, using ionic liquids over common organic solvents has several challenges, i.e., higher viscosity (lower diffusivity) than common organic solvents; lower solubility of reaction gases and large number of high-melting solids not liquids at processing conditions. Coupling ionic liquids with compressed gases systems may overcome most of these difficulties for their applications in separations, reactions, materials processing and engineering applications. To further develop these processes, phase behavior and phase equilibrium knowledge are of essential significance. The main objective of this research is to investigate high pressure global phase behavior and measure phase equilibrium of ionic liquids and compressed gases for their applications as reaction media for hydrogenation and hydroformylation reaction and as working fluids for absorption air conditioning systems. This research investigates imidazolium ionic liquids with various alkyl groups and anions and two compressed gases: carbon dioxide (CO2) and 1,1,1,2- ii Tetrafluoroethane (R-134a). The global phase behavior and phase equilibria are measured in the temperature range from approximately 0°C to 105°C and pressure up to 330 bar. Binary systems of R-134a with ionic liquids of [EMIm][Tf2N], [HMIm][Tf2N], [HMIm][PF6], [HMIm][BF4], and [BMIm][PF6] indicate a Type V system according to the classification of Scott and van Konynenburg. Regions of multiphase equilibria exist, viz. vapor liquid equilibrium, vapor liquid liquid equilibrium, liquid liquid equilibrium; while Type III phase behavior for [HMIm][Br] and R-134a is observed, which provides a novel purification method to separate [HMIm][Tf2N] from [HMIm][Br] after synthesis. The phase behavior of CO2 and all ionic liquids indicate Type III systems. The effects of ionic liquid structures on the solubility, lower critical end-point (LCEP) and mixture critical points are also investigated. Complete phase behavior study with the reactant, product, CO2 and ionic liquids for hydrogenation and hydroformylation reactions are accomplished, and volume expansion and molar volume data of liquid phase with CO2 pressure are measured simultaneously. Two regions of reaction rate with different primary phenomena can be explained by phase behavior knowledge: dilution effect and reactant partitioning. The unique phase properties of IL/CO2 suggest an ease product purification process and make it a favorable biphasic solvent system. Detailed phase behavior and equilibrium help understand fully the kinetics results, determine the operating conditions, choose appropriate separation process and properly design an optimal reaction system. iii The understanding and quantitative modeling of the high-pressure phase behavior and equilibria data are essential for process design and simulation. The Peng-Robinson equation of state model with van der Waals 2-parameter mixing rule is chosen to correlate the experimental data and predict phase equilibrium. Thermodynamic modeling of an absorption air conditioning system using ILs and compressed gases as working fluids is developed. This work reveals that a biphasic reaction system with IL/CO2 for homogeneously catalyzed reactions provides a highly tunable, flexible and economic platform for reactions and separations. However, without understanding the phase equilibrium, the kinetics results cannot be properly interpreted. This work also demonstrates that the absorption refrigeration system using ionic liquids and compressed gases in vehicles is feasible using just the waste heat from the engine and can provide comparable cooling capacity as vapor compression system. The common vapor compression system diverts work from the engine to power the air conditioning system and this adds to fuel consumption and pollution. iv Acknowledgements I want to express sincere gratitude to my advisor, Dr. Aaron M. Scurto, for his guidance, enthusiasm and encouragement throughout my graduate study at the University of Kansas. He inspired me to explore ideas and carry out research in the field of thermodynamics. I really appreciate his help and patience. I am grateful to Professor Kyle Camarda, Dr. Jyun-Syung Tsau, Professor Jenn-Tai Liang, Professor Laurence Weatherley and Professor Brian B. Laird for their inspirational and valuable advice. I also want to thank Dr. Mark B. Shiflett and Dr. A. Yokozeki for their helpful discussions and rewarding collaborations. I would like to give my special thanks to Mr. Alan Walker and Mr. Scott Ramskill for their excellent work and help on setting up and maintaining experiment equipment. I would like to thank the faculty and staff of the Department of Chemical and Petroleum Engineering, Center for Environmentally Beneficial Catalysis (CEBC) and Center of Tertiary Oil Recovery Project (TORP), especially Dr. Fenghui Niu, Dr. Claudia Bode, Mr. Ed Atchison, Mrs. Deanna Bieberly, Dr. Tie-pan Shi, Dr. Min Cheng, Dr. Chicheng Ma, and the friends I made during my graduate study for their encouragement and friendship. I wish to thank my group mates, Jay Schleicher, Azita Ahosseini, Sylvia Ogechi Nwosu, for their support, discussion and cooperation. Finally, I want to express my deepest appreciation to my family: my daughter, Katherine, son Kevin, husband Bao Lin and my parents: Lanting Ren and Minru Bao for their endless love and persistent support for me. v Dedicated to my loving family: Katherine, Kevin, Bao Lin and my parents vi List of Figures Figure 1.1 Illustrations of common cation classes and anions used with ionic liquids......2 Figure 1.2 Other cations used in ionic liquids ...............................................................2 Figure 1.3 Literature survey on publications of ionic liquids. All data is till September, 2009 ......6 Figure 2.1 Diagram of experimental apparatus. (1) Gas Cylinder; (2) Syringe Pump; (3) Heater/Circulator; (4) Immersion Heater/Circulator; (5) Water Bath; (6) High pressure view cell; (7) Mixing Bar; (8) Lab Jack; (9) Computer; (10) Cathetometer with Telescope (11) Vacuum Pump.............................................................................51 Figure 2.2 High- pressure equilibrium view-cell.........................................................57 Figure 2.3 Liquid-liquid-vapor equilibria....................................................................64 Figure 2.4 Phase equilibrium data of Decane/CO2 71°C with literature data of Gasem’s group[2] and Robinson Jr.’s group[5]...........................................................65 Figure 2.5 Phase equilibrium data of Decane/CO2 at 71°C with literature data of Sage’s group[1], Schucker’s group [4] ........................................................................66 Figure 2.6 The mixture density data of Decane/CO2 at 71°C with literature data of Gasem’s group [2] and Robinson Jr.’s group[5]..........................................................67 Figure 2.7 Setup to measure the global phase behavior...............................................70 Figure 2.8 Setup of autoclaves.....................................................................................71 Figure 2.9 Inductively Covered Plasma (ICP) Spectroscopy ......................................77 Figure 2.10 Set up of ICP ...........................................................................................78 Figure 2.11 The whole set up of UV-vis high pressure polarity measurement ...........80 Figure 2.12 Picture of the high pressure UV-vis Cell..................................................82 vii Figure 2.13 The detailed set up of the high pressure UV-vis Cell...............................82 Figure 4.1 Common types of global phase diagrams according to their Scott and van Konynenburg [1] and Bolz et al. [3]. .........................................................................121 Figure 4.2 Ionic liquid cations and anions and refrigerant used in this study: a) cation structures; b) anion structures; c) refrigerant gas: 1,1,1,2-tetrafluoroethane
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