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Competitive Catalytic Hydrogenation of Benzene, Toluene, and the Polymethylbenzenes on Platinium

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Competitive Catalytic Hydrogenation of Benzene, Toluene, and the Polymethylbenzenes on Platinium University of Tennessee, Knoxville TRACE: Tennessee Research and Creative Exchange Doctoral Dissertations Graduate School 8-1961 Competitive Catalytic Hydrogenation of Benzene, Toluene, and the Polymethylbenzenes on Platinium Charles Phillip Rader University of Tennessee - Knoxville Follow this and additional works at: https://trace.tennessee.edu/utk_graddiss Part of the Chemistry Commons Recommended Citation Rader, Charles Phillip, "Competitive Catalytic Hydrogenation of Benzene, Toluene, and the Polymethylbenzenes on Platinium. " PhD diss., University of Tennessee, 1961. https://trace.tennessee.edu/utk_graddiss/2953 This Dissertation is brought to you for free and open access by the Graduate School at TRACE: Tennessee Research and Creative Exchange. It has been accepted for inclusion in Doctoral Dissertations by an authorized administrator of TRACE: Tennessee Research and Creative Exchange. For more information, please contact [email protected]. To the Graduate Council: I am submitting herewith a dissertation written by Charles Phillip Rader entitled "Competitive Catalytic Hydrogenation of Benzene, Toluene, and the Polymethylbenzenes on Platinium." I have examined the final electronic copy of this dissertation for form and content and recommend that it be accepted in partial fulfillment of the equirr ements for the degree of Doctor of Philosophy, with a major in Chemistry. Hilton A. Smith, Major Professor We have read this dissertation and recommend its acceptance: William T. Smith, William E. Bull, Carl Buehler Accepted for the Council: Carolyn R. Hodges Vice Provost and Dean of the Graduate School (Original signatures are on file with official studentecor r ds.) August 101 1961 To the Graduate Council: I am submitting herewith a thesis written b,y Charles Phillip Rader entitled 11Competitive Catalytic Hydrogenation of Benzene, Toluene, and the Polymethylbenzenes on Platinumo11 I recommend that it be accepted in partial fulfillment of the requirements for the degree of Doctor of Philosophy, with a major in Chemistr,yo �Major Professor 12�� We have read this thesis and recommend its acceptance: Accepted for the Oouncilz . cia, Dean of �bool COMPETITIVE CATALYTIC HYDROGENATION OF BENZENE , TOLUENE, AND THE POLYMETHYLBENZENES ON PLATINUM Thesis A Presented to the Graduate Council of The University of Tennessee In Partial Fu lfillment of the Requirements for the Degree Doctor of Philosophy by Charles Phillip Rader August 1961 33 ACKNOWLEDGMENT The author wishes to express sincere appreciation to Dr. Hilton A. Smith for the capable guidance he ha s provided by giving so freely of his time, his talents, and himself during the course of this work. He desires to thank his wife , Clarita Anne, for providing the inspira­ tion for the successful comp letion of this research, and his daughter, Clarita Marie, for giving it a more profound purposea Appreciation is also due to his mothe r and father for the wealth of encouragement they have furnished. He is grateful to the National Science Foundation for granting the fellowships which enabled this research to be carried outo 525437 TO CLARITA ANNE AND CLARITA MARJE TABlE OF CONTENTS CHAPmR PAGE INTRODUCTION • • • • • • • • • • • • • • • • • • • • • • • • • 1 A. Purpose of This Research 0 0 • • • • • • • • • • 0 • • • • 1 B. Historical Background. • . • • • • • • • • • • • • 1 c. Nature of Hydrogenation Catalysts. 0 • • • • • 6 • • • • • 4 D. Thermodynamics and Kinetics •• • • • • • • • • • • • • • • 10 E. Stereochemistry and Mechanism. 0 • • • • • • • • • • • • • 13 F. Competitive Catalytic Hydrogenation. • • • • • • • • • • • 15 n. THEORETICAL DISCUSSION • • • • • • o • • • • • • • • • 0 • • • 18 A. Competitive Hydrogenation and the Hydrogenation Mechanism of the Benzene Nucleus o o • o • • • • • • • 0 18 B. Mathematical Analysis . • • 0 • 0 • 0 • • • • • • • • 0 • • 25 IIT• EXPERIMENTA� • • • • • • o • • • • o • • • • • • • • • • • • • 36 A. Materials. ••••o••••o• • • • • • • • • • • • 0 0 36 1. Platinum OXide Catalyst. • • 0 • • • • • • • • • • • • 36 2. Acetic Acid. • • • • • • 0 • 0 • • • • • • • • • • • 0 36 3. Hydrogen • o ••••••••••••••o • • • • • • 37 4. Benzoic Acid 0 • • • • • • • • • • • • 0 • • • • • • • 37 5. Benzene •••••••••• o • • • • • • • • • • • • • 37 6. Toluene . • • • • • • • • • • • • • • • • • • • • • • • 36 7. ortho-Xylene • • . • 0 • • 0 . • • • • . • • • • • • 36 B. meta-Xylene . • • • . • . • . • • • • • • • • • • • • 36 9. para-Xylene . • • • • • • • • • • • • • • • • 0 • • • • 39 iv CHAPI'ER PA GE Hemimellitene (1,2,3-Trimethylbenzene)o • 0 • 0 0 . .. 40 11 . Pseudocumer.e (1,2,4-Trimethylbenzene ) ••• • • • • 0 40 12. Mesitylene (1,3,5-Trimethylbenzene ) • • 0 0 • 41 13o P.rehnitene (1,2,3,4-Tetramethylbenzene ) • • • 0 0 0 • 41 14'o Isodurene (1,2,3,5-Tetramethylbenzene ) o • • 0 0 0 41 15o Durene (1,2,4,5-Tetramethylbenzene) • o • • • 0 0 0 0 42 16. Pentamethylbenzene. o o • o ••• o o • o • 0 0 0 42 17 o Hexamethylbenzene o o 0 0 0 0 0 0 0 • 0 0 0 0 0 0 43 HYdrogenation Apparatus o • 0 0 0 0 0 • 0 0 • 0 0 44 Hydrogenation Procedure o • • • o 0 0 0 0 oooeoo 45 1. General o • o • o o • • • o o o o 0 0 0 0 000000 45 2. Hydrogenation of Individual Hydrocarbons •• o o o o • 46 3. Binar,y Competitive Hydrogenations o •• 0 0 0 • 0 0 0 48 Spectrophotometric Analyses o o o o o o • • 0 • 0 . 0 0 49 1. Method and Apparatus. o • o•oooo 0 0 0 0 49 2 o Experimental Procedure o • o o o • o o e • o o o • • o 52 3. Development of Analytical Method. • • • 0 0 0 0 0 0 0 54 4. Verification of Analytical Method 0 0 • • 0 • • 0 0 • 56 E. Treatment of Experimental Data ••• o ••• o o o • • • • 62 IV o BESULTS • o • • o • o o o • • • • • • • o • o • o o • o o 66 A. �drogenation of Individual Hydrocarbons •• 0 • 0 0 0 66 Bo Competitive Hydrogenation of Benzene and Toluene ••• 0 0 69 c. Competitive Izydrogenation of Benzene with the Xylenes • • o o • • o o • o • o • • • o • o • • • • 73 v CHAPTER PAGE D. Competitive Hydrogenation of Toluene and the Xylenes • • • • • o 0 • • • • 0 0 • 0 • 77 E. Competitive Hydrogenation of the Xylenes. • 0 0 0 0 • • 0 61 F. Competitive Hydrogenation of the Trimethylbenzenes • o • ooeoo••ooooooooo 66 G. Competitive Hydrogenation of the Tetramethylbenzenes, Pentamethylbenzene1 and Hexamethylbenzene o 0 • 0 0 0 0 91 v. INTERPRETATIONS AND CONCLUSIONS 0 0 0 0 0 • 0 0 0 0 0 0 0 0 0 97 General Interpretation. • • • 0 0 0 0 0 0 0 0 0 0 0 0 97 B. Relation between Molecular Structure , Ease of Adsorption, and Reduction Rate •• o o •••• • • 0 0 0 101 c. Relation of This Investigation to the aydrogenation Me chanism of the Benzene Nucleu s •• o 0 0 0 0 0 0 0 0 • 113 VI. SUMMARY 0 0 0 0 0 0 • 0 0 0 o e o o 0 0 0 • 0 • 0 0 0 0 0 119 BIBLIOGRAPHYo • o 0 0 0 0 0 0 0 • 0 0 0 Cll 0 0 0 0 0 0 0 0 • 0 • 0 • 122 LIST OF TABLES TABlE PAGE I. Experimental Results of the Analyses of Benzene-ortho xYlene Solutions of Known Concentrations o • • • • • • • • 59 Smnmary of Results of Analyses of Binary Acceptor Solutions of Known Concentrations••••• o 0 • • 0 • • 0 60 lli. Comparison of Standard Rate Constants for the Hydrogenation of Individual a1drocarbons at 30° with Those Obtained in Previous Work o • • • • • 0 • • • 0 67 IV. Acceptor Concentration Data for the Competitive aydrogenation of Benzene and Toluene o • o • • • 0 • • • • 70 V., Cbmpetitive Adsorption Equilibrium Constants from the Competitive Hydrogenation of Benzene with the Xylenes • • • • • • • • • • o • • o • • • • • • 0 76 VI. Competitive Adsorption Equilibrium Constants from the Competitive Hydrogenation of Toluene with the �lenes. • . • • . • • • . • • . • • • • • • • • • • • • • 19 VII. Competitive Adsorption Equilibrium Constants from the Competitive Hydrogenation of the Iylenes • • • • • • ••• 83 VIII., Smnmary of the Experimental Values of the Competitive Adsorption Equilibrium Cbnstants from the Competitive Hydrogenation of Benzene, Toluene, and the Iylenes • • • • 86 IX. Competitive Adsorption Equilibrium Constants for the Competitive aydrogenation of the Trimeteylbenzenes • • • • 92 vii TABlE .PAGE X.. Competitive Adsorption Equilibrium Constants for the Competitive Hydrogenation of the Tetramethy1- benzenes, Pentamethylbenzene, and Hexamethy1benzene ....o o 95 XIo A Comparison of Relative Reduction Rates with the Competitive Adsorption Equilibrium Constants for the Competitive Hydrogenation of Toluene and the Polymethylbenzenes with Benzene.. " • o o • 0 " • 0 " 0 102 LIST OF FIGURES FIGURE PAGE l o Plot of Potential Energy versus Reaction Coordinate for a Reaction Taking Place on a Catalyst Surface ••o . 0 0 • 7 2 o Ultraviolet Absorption Spectra of Benzene1 Toluene1 and the xYlenes in Glacial Acetic Acid o o • o o o • o • e o 55 3. Plots of Absorbancy.varsus Concentration for a Series of Standard meta-Xylene Solutions o o o o o o o • o • 57 4 o Plot of Log Hydrogen Pressure versus Time for Hydrogenation of para-Xylene o • o o o o o o o • • • o • • • 63 5 o Plot of Log Toluene Concentration versus Log Benzene Concentration for the Competitive Hydrogenation of Benzene and Toluene. o •• o • o ••• o • 0 • • • • 0 • 0 0 72 6. Plot of Log Xylene Concentration versus Log Benzene �- Concentration for the Com petitive aydrogenation of Xylene and Benzene •••o • o o ••••• o • • • • • • 74 �- 7. Plot of Log meta-Xylene Concentration versus Log Toluene Concentration for the Competitive Hydro- genation of -Xylene and Toluene •••o • o o • • • • • • 8 � 7 8. Plot of Log or tho-Xylene Concentration versus Log para-Xylene Concentration for the Competitive Hydrogenation of ortho-Xylene and para-Xylene. • o •
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