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Equilibrium Limitations and Selectivity On EQUILIBRIUM LIMITATIONS AND SELECTIVITY ON CONVERSION OF GLYCEROL TO PROPYLENE GLYCOL ______________________________________________________ A Thesis presented to the Faculty of the Graduate School University of Missouri- Columbia ______________________________________________________ In Partial Fulfillment of the Requirements for the Degree Master of Science _______________________________________________________ by LIZANETTE RIVERA-RAMOS Dr. Galen J. Suppes, Thesis Supervisor AUGUST 2006 © Copyright by Lizanette Rivera-Ramos 2006 All Rights Reserved The undersigned, appointed by the Dean of the Graduate School, have examined the thesis entitled EQUILIBRIUM LIMITATIONS AND SELECTIVITY ON CONVERSION OF GLYCEROL TO PROPYLENE GLYCOL presented by Lizanette Rivera-Ramos a candidate for the degree of Master of Science and hereby certify that in their opinion it is worthy of acceptance. Dr. Galen J. Suppes Dr. Thomas R. Marrero Dr. Hsieh ACKNOWLEDGEMENTS I would like to express my sincere gratitude to my graduate advisor Dr. Galen Suppes, for his guidance, support, and contributions through my graduate studies. I would also like to thank Dr. Thomas R. Marrero for his comments and suggestions. Both of them had been excellent role models over the past years and I would like to thank them for giving me the opportunity to be their student. Appreciation is extended to Chuang-Wei “Roger” Chiu for provided me the guidance of an experienced researcher throughout my experimental work. Finally, I would like to thank the lab. team for their constant support and help in my research endeavors. Thank you one and all. ii TABLE OF CONTENTS ACKNOWLEDGEMENTS ................................................................................ii LIST OF TABLES...........................................................................................vii LIST OF FIGURES..........................................................................................ix CHAPTER 1...................................................................................................................... 1 1. INTRODUCTION .................................................................................................. 1 1.1 Introduction to Bio-Based Products........................................................... 1 1.2 Propylene Glycol ....................................................................................... 3 1.2.1 Physical and Chemical Properties ................................................................. 3 1.2.2 Uses ................................................................................................................... 4 1.3 Background Literature............................................................................... 4 1.4 Research Emphasis .................................................................................. 5 2. EXPERIMENTAL MATERIALS AND METHODS .......................................... 8 2.1 Introduction ............................................................................................... 8 2.2 Materials ................................................................................................................ 8 2.2.1 Glycerol .............................................................................................................. 8 2.2.2 Propylene Glycol (PG) ..................................................................................... 8 2.2.3 Hydroxyacetone (Acetol) ................................................................................. 9 2.2.4 Hydrogen ........................................................................................................... 9 2.2.5 Catalyst .............................................................................................................. 9 2.2.6 n-Butanol ........................................................................................................... 9 iii 2.3 Chemical Reaction Apparatus................................................................... 9 2.3.1 Introduction ........................................................................................................ 9 2.3.2 Feed Area ........................................................................................................ 10 2.3.3 Pre-heat and Evaporation ............................................................................. 10 2.3.4 Reactor ............................................................................................................. 11 2.3.5 Condenser ....................................................................................................... 11 2.4 Procedures.............................................................................................. 12 2.4.1 Experimental Procedures .............................................................................. 12 2.4.2 Method of analysis ......................................................................................... 12 2.6 Data Reduction ....................................................................................... 13 3. VERIFYING EQUILIBRIUM OF GLYCEROL TO PROPYLENE GLYCOL REACTION ...................................................................................................................... 14 3.1 Reaction of Glycerol to Propylene Glycol................................................ 15 3.2 Reaction of Propylene Glycol to Acetol ................................................... 18 3.4 Reaction of Acetol to Propylene Glycol ................................................... 22 3.5 Equilibrium Constant and Gibbs Free Energy ......................................... 26 4. TRENDS IN BYPRODUCTS ............................................................................ 35 4.1 Reaction of Glycerol to Propylene Glycol................................................ 36 4.2 Reaction of Propylene Glycol to Acetol ................................................... 43 4.4 Reaction of Acetol to Propylene Glycol .................................................. 49 5. CATALYST PRODUCTIVITY .......................................................................... 54 5.1 Reaction of Glycerol to Propylene Glycol................................................ 55 6. CONCLUSIONS ................................................................................................. 61 iv 6.1 Effect of Reaction Temperature .............................................................. 61 6.1.1 Reaction of Glycerol to Propylene Glycol ................................................... 61 6.1.2 Reaction of Propylene glycol to Acetol ....................................................... 61 6.1.3 Reaction of Acetol to Propylene Glycol ...................................................... 62 6.2 Effect of System Pressure....................................................................... 62 6.2.1. Reaction of Glycerol to Propylene Glycol .................................................. 62 6.2.2. Reaction of Propylene Glycol to Acetol ..................................................... 62 6.2.3. Reaction of Acetol to Propylene Glycol ..................................................... 63 6.3 Effect of Residence Time ........................................................................ 63 6.3.1. Reaction of Glycerol to Propylene Glycol .................................................. 63 6.3.2. Reaction of Propylene Glycol to Acetol ..................................................... 63 6.3.3. Reaction of Acetol to Propylene Glycol ..................................................... 64 6.4. Effect of H 2: Glycerol Mole Ratio............................................................ 64 6.5. Effect of Water Content.......................................................................... 65 6.5.1. Reaction of Glycerol to Propylene Glycol .................................................. 65 6.6 Carbon Efficiency .................................................................................... 65 6.6.1 Reaction of Glycerol to Propylene Glycol ................................................... 65 6.7 Recommendations .................................................................................. 65 REFERENCES ............................................................................................................... 66 APPENDIX ...................................................................................................................... 68 APPENDIX A................................................................................................. 69 ADDITIONAL GRAPHS AND TABLES ......................................................... 69 A.1 Reaction of Glycerol to Propylene Glycol ...................................................... 69 v A.2 Reaction of Acetol to Propylene Glycol ......................................................... 72 A.3 Reaction of Propylene Glycol to Acetol ......................................................... 75 APPENDIX B................................................................................................. 78 SAMPLE CALCULATIONS ........................................................................... 78 APPENDIX C ................................................................................................ 84 EQUIPMENT PICTURES.............................................................................. 84 APPENDIX D ................................................................................................ 95 PHYSICAL AND CHEMICAL PROPERTIES ...............................................
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