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The Stereospecific Hydrogenation and Dehydrogenation of Rosin and Fatty Acids

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The Stereospecific Hydrogenation and Dehydrogenation of Rosin and Fatty Acids Louisiana State University LSU Digital Commons LSU Master's Theses Graduate School 2011 The ts ereospecific yh drogenation and dehydrogenation of rosin and fatty acids Edward O'Brien Louisiana State University and Agricultural and Mechanical College, [email protected] Follow this and additional works at: https://digitalcommons.lsu.edu/gradschool_theses Part of the Chemical Engineering Commons Recommended Citation O'Brien, Edward, "The ts ereospecific yh drogenation and dehydrogenation of rosin and fatty acids" (2011). LSU Master's Theses. 2081. https://digitalcommons.lsu.edu/gradschool_theses/2081 This Thesis is brought to you for free and open access by the Graduate School at LSU Digital Commons. It has been accepted for inclusion in LSU Master's Theses by an authorized graduate school editor of LSU Digital Commons. For more information, please contact [email protected]. THE STEREOSPECIFIC HYDROGENATION AND DEHYDROGENATION OF ROSIN AND FATTY ACIDS A Thesis, Submitted to the Graduate Faculty of the Louisiana State University and Agricultural and Mechanical College in partial fulfillment of the requirements for the degree of Master of Science in Chemical Engineering In The Department of Chemical Engineering by Edward O’Brien B.S., The University of Dallas, 2009 December 2011 ACKNOWLEDGEMENTS I would like to thank my advisor Dr. Kerry Dooley for his patience, direction, and mentorship throughout this project. Thanks to Arizona Chemical for their financial support throughout this project. I would also like to thank Dr. W. Dale Treleaven for his assistance with the NMR, and thanks to Paul Rodriguez and Joe Bell for their assistance in the machine shop. Finally, I would like to thank Grady Thigpen and Cassidy Sillars for their contributions in the lab. ii TABLE OF CONTENTS ACKNOWLEDGEMENTS…………………………………………………………………….....ii LIST OF TABLES…………………………………………………………………………….......v LIST OF FIGURES……………………………………………………………………………....vi ABSTRACT..................................................................................................................................vii CHAPTER 1: INTRODUCTION AND LITERATURE REVIEW…………...……………….....1 1.1 Introduction and Goals…………………………………………………………...........1 1.1.1 Literature Review: Hydrogenation of Abietic Acid to Abietyl Alcohol...............3 1.1.2 Literature Review: Dehydrogenation of Abietic Acid..........................................4 1.1.3 Literature Review: Hydrogenation of Fatty Acids................................................5 CHAPTER 2: EXPERIMENTAL PROCEDURES........................................................................8 2.1 Hydrogenation of Abietic Acid......................................................................................8 2.1.1 Feed Composition...........................................................................................8 2.1.2 Reaction Procedure.........................................................................................9 2.1.3 Sample Analysis............................................................................................10 2.2 Dehydrogenation of Abietic Acid................................................................................11 2.2.1 Feed Composition and Catalyst Characterization.........................................11 2.2.2 Reaction Procedure.......................................................................................12 2.2.3 Sample Analysis............................................................................................12 2.3 Selective Hydrogenation of Fatty Acids to Fatty Alcohols.........................................13 2.3.1 Feed and Catalyst Characterization..............................................................13 2.3.2 Reaction Procedure.......................................................................................13 2.3.3 Sample Analysis............................................................................................14 CHAPTER 3: RESULTS AND DISCUSION...............................................................................15 3.1 Compound Identification by GCMS............................................................................15 3.2 Catalysts and Their Sources.........................................................................................16 3.3 Hydrogenation of Abietic Acid....................................................................................20 3.4 Dehydrogenation of Abietic Acid................................................................................27 3.4.1 Dehydrogenation of Abietic Acid in Small Bomb Reactors.........................27 3.4.2 Equilibrium Analysis for Conversion to Dehydroabietic Acid.....................30 3.4.3 Dehydrogenation Results for Larger Reactors..............................................32 3.4.4 Kinetic Analysis for the Dehydrogenation Results.......................................39 3.5 Selective Hydrogenation of Fatty Acids to Fatty Alcohols.........................................45 CHAPTER 4: CONCLUSIONS....................................................................................................56 REFERENCES..............................................................................................................................58 APPENDIX A – GAS CHROMATOGRAPH (GC) AND MASS SPECTRUMS DETAILS......61 iii APPENDIX B – TABULAR REACTION DATA AND RESULTS............................................65 VITA..............................................................................................................................................76 iv LIST OF TABLES Table 1.1: Dehydrogenation Tests, Inert Gas, from Literature........................................................5 Table 2.1: Composition of Synthetic DTO (AZ-1)..........................................................................8 Table 3.1: Catalysts Used..............................................................................................................17 Table 3.2: Results of Synthetic DTO Hydrogenations in Ethanol Solvent....................................26 Table 3.3: Estimated Thermodynamic Properties, Joback Method...............................................31 Table 3.4: Dehydrogenation Tests, Air, 1 atm...............................................................................35 Table 3.5: Dehydrogenation Tests, Inert Gas................................................................................36 Table 3.6: Kinetics Results, Dehydrogenation Tests.....................................................................40 Table 3.7: Kinetics Results, Hydrogenation with Pd Catalysts.....................................................48 Table 3.8: Kinetic Results, Hydrogenation with Alloy Catalysts..................................................49 Table 3.9: Kinetic Results, Hydrogenation with Alloy Catalysts and Methanol...........................51 Table 3.10: Hydrogenation with Alloy Catalysts, and Methanol..................................................53 Table A.1: The Parameters for Sylv4............................................................................................61 Table A.2: The Parameters for Sylv42..........................................................................................61 Table A.3: The Parameters for AzFAMES....................................................................................62 Table A.4: The Parameters for Az9...............................................................................................62 Table B.1: Bomb Reactor Raw Data..............................................................................................65 Table B.2: Raw Results of the Large Scale Dehydrogenation Reactions......................................67 Table B.3: Raw Results for Fatty Acid Hydrogenation Experiments............................................68 Table B.4: Dehydrogenation Results.............................................................................................69 Table B.5: Composition Percent Results for the Rosin Hydrogenation Runs...............................71 Table B.6: Composition Results for Hydrogenation of Fatty Acid Runs......................................72 v LIST OF FIGURES Figure 1.1: Linoleic Acid.................................................................................................................1 Figure 1.2: Abietic Acid and Pimaric Acid Structures....................................................................2 Figure 1.3: Oleyl Alcohol, Abietyl Alcohol and Dehydroabietic Acid...........................................3 Figure 3.1a: Comparison of Pd catalysts, reaction of linoleic acid...............................................22 Figure 3.1b: Comparison of Pd catalysts, reaction of abietic acid.................................................23 Figure 3.2a: Comparison of other catalysts, reaction of linoleic acid...........................................24 Figure 3.2b: Comparison of other catalysts, reaction of abietic acid.............................................25 Figure 3.3a: Comparison of simple Pd and Pt catalysts for selectivity to dehydroabietic acids...28 Figure 3.3b: Comparison of Ni, Ru and Pd/Cu catalysts for selectivity to dehydroabietic acids.29 Figure 3.4: Reaction to dimer, According to Arizona Chemical and Fujii et al............................34 Figure 3.5: % Conversion to Dehydrogenation Products for Catalysts “B” and “E”....................45 Figure A.1: Chromatogram of 18-2A from the Dehydrogenation Runs........................................63
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