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Rhenium Trioxide, Rhenium Heptoxide and Rehnium Trichloride As Hydrogenation Catalysts

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Rhenium Trioxide, Rhenium Heptoxide and Rehnium Trichloride As Hydrogenation Catalysts Brigham Young University BYU ScholarsArchive Theses and Dissertations 1958-07-21 Rhenium trioxide, rhenium heptoxide and rehnium trichloride as hydrogenation catalysts William J. Bartley Brigham Young University - Provo Follow this and additional works at: https://scholarsarchive.byu.edu/etd BYU ScholarsArchive Citation Bartley, William J., "Rhenium trioxide, rhenium heptoxide and rehnium trichloride as hydrogenation catalysts" (1958). Theses and Dissertations. 8161. https://scholarsarchive.byu.edu/etd/8161 This Thesis is brought to you for free and open access by BYU ScholarsArchive. It has been accepted for inclusion in Theses and Dissertations by an authorized administrator of BYU ScholarsArchive. For more information, please contact [email protected], [email protected]. (QJ> I ,_t;z .1537 {1~ c~z- RHENIUMTRIOXIDE, RHENIUMHEPTOXIDE AND RHENIUMTRICHLORIDE AS HYDROGENATIONCATALYSTS A Thesis Submitted to the Department of Chemistry Brigham Young University Provo, Utah In Partial Fulfillment Of the Requirements for the Degree of Master of Science by William J. Bartley August, 1958 This thesis by William J. Bartley is accepted in its present form by the Department of Chemistry of the Brigham Young University as satisfying the thesis requirements for the degree of Master of Science. ii ACKNOWLEDGEMENTAND DEDICATION 'fhe author wishes to express his sincere appreciation and thanks to all who have assisted in any way toward the com- pletion of this work. Special thanks is extended to Dr. H. Smith Broadbent, who gave freely of his kind assistance and excellent advice. To my parents, Mr. and Mrs. Wm. Bartley, goes my grati- tude and appreciation for their undeviating support. My love and devotion go to my wonderful wife, Earlene, for her patience and encouragement. To her this work is dedicated. The author is also indebted to the United States Air Force--Office of Scientific Research under whose contract this study was made. iii TABLEOF CONTENTS page LIST OF TABLESAND'FIGURES viii I• INTRODUCTION. • •. • • • • • •· . ...... .... ... ..... 1 II. LITERATUREREVIEW • • • • • • • • • • • • • • • • • • • 3 4 Catalytic Hydrogenation •••••••••••••• 3 1. General••• ••••• • • ••••••••• 3 2. Catalysis• • • ••••••••••••••• 3 3. Adsorption •••••••••••••••••• 4 4. lictive Centers •••••••••••••••• 4 s. Poisoning •••••••••••••••••• 6 6. Selectivity ••••••••••••••••• G 7. General Methods of Hydrogenation ••••••• 7 s. Reduction of the Various Functional Groups.• 8 9. Conclusion •• ~~ •••••• • ••••••• 9 B. Rhenium Beptoxide. • ••••••••••••••• 9 1. Preparation•.• ••••••••••••• • 9 2. Properties.• ••••••••••••••• • 10 C. Rhenium Trioxide ••••••••••••••••• 12 1. Preparation••.•• • • • • • •. • • • •. 12 2. Properties.•.•• ••••••••• • •• • 13 D. Rhenium Trichloride: Inorganic Chemistry ••••• 14 1. Preparation •••••••• , ••••••••• 14 2. Properties •••••••••••••••••• 15 3. Analysis ••••••••••••••••••• 17 · a. Quantitative Analysis for Chlorine in Rhenium Chlorides •••••••••••• 17 b. Qualitative Crystal Tests •••••••• 17 E. Rhenium 'l'richloride: Organic Chemist1"7 •••••• 17 1. Preparation of Trimethylrhenium and 'l'ri- ethylrhenium ••••••••• • ••••••• 17 2. Properties of Re(CH ) and Re(C B ) •••• • 17 3 2 3. Preparation of Rhenium.3 Ethoxide and5 3 Iso- propoxide •••••••••••••••••• 18 4. Properties of Rhenium Ethoxide and Iso- propoxide •••••••••••••••••• 18 F. Analysis of Rhenium Compounds ••••••••••• 18 lo Quantitative Analysis• •• • ••••••• • 18 2. Oxidation State Determination •••••••• 18 III. EXPERIMENTAL. • • • • • • • • • • • • • • • • • • • • • 19 Ii. General. • • • • • • • • • • • • • • • • • • • • • 19 1. Catalyst Codes. • • • • • • • • • • • • • • • 19 2. Catalyst Preparation. • • • • • • • . • . • • 19 a. Rhenium Trioxide • • • • • • • • • • • • 19 iv page b. Rhenium Heptoxide •••••••••• • 19 c. Rhenium Trichloride •••••••••• 20 Method of Hydrogenation •••••••••• 20 4. Method of Analysis ••••••••••••• 21 a. Catalysts: Ultimate Analysis ••••• 21 b. Catalysts: Oxidation State Determina- tion ••••••••••••• J ••• 22 c. Analysis of Hydrogenated Organic Sub- strates ••••••••••••••• • 22 B. Catalyst Preparations and Analyses• •••••• 23 I. Rhenium Trioxide Catalysts ••••••• • • 23 2. Rhenium Heptoxide Catalysts: !;! .§ili in Acetic Acid ••••••• • •••••••• 26 3. Rhenium Heptoxide Catalysts: Reduced !B, Situ • •••• , • • • • • • • • • • • • • • 27 c. Hydro~tion Experiments. • •••••••••• 28 1. Hydrogenation with Rhenium Trioxide De- rived Catalysts •••••••••••••• 28 (a) 3-Pentanone ••••••••••••• 28 (b) 2,3-Butanedione ••••••••••• 28 (c) Cyclohexanone •••••••••••• 28 (d) Crotonaldehyde •••••••••••• 28 (e) Benzaldehyde •• , ••••••••••• 29 (f) !!-Nitrobenzaldehyde ••••••••• 29 ( g) 1-Hexene. • • • • • • • • • • • • • • 29 (h) Cyclohexene ••••••••• • ••• 29 (i) Styrene • • • • • • • • • • • • • • • 30 (j) Benzene ••••••• • • • • ■ • • • 30 (k) Pyridine. • • .. • • • • • • • • • • • 30 (I) 2-Nitropropane •••••••••••• 31 (m) Nitrocyclohexane ••• • ••••••• 31 (n) Nitrobenzene ••••••••••••• 31 (o) .2-Nitrophenylacetic Acid ••••••• 31 (p) Formic Acid • • • • • • • • • • • • • 32 (q) Acetic Acid ••••••••••••• 32 (r) Butyric Acid ••••••••••• • • 32 (s) Isobutyric Acid ••••••••• • • 32 (t) Crotonic Acid •••••••••• • • 32 (u) Valerie Acid ••••••••••••• 33 (v) Caprylic Acid ............ 33 (w) Undecylenic Acid ••••••••••• 33 (x) Benzoic Acid ••••••••••••• 33 (y) Ethyl Acetate •••••••••••• 34 (z) Butyl Butyrate •••••••••••• 34 (aa) Ethyl Benzoate •••••••••••• 34 (bb) Hydrazobenzene •••••••••••• 34 (cc) Azobenzene •••••••••••••• 35 (dd) Capronitrile ••••••••••••• 35 (ee). Acetamide • • • • • • • • • • • • • • 36 (ff) Benzamide • • • • • • • • • • • • • • 36 (gg) Acetanilide ••••••••••••• 36 2. Hydrogenations With Rhenium Heptoxide De- rived Catalysts Reduced _!!.2!1!:! •••••• 36 (a) Acetic Acid ••••••••••••• 36 V page (b) Butyric Acid. • . • . • . • 37 (c) Caprylic Acid • • • . • . • . • 37 3. Hydrogenations with Rhenium Heptoxide De- rived Catalysts Reduced .!!!.§!!!! • • • • . • 37 (a) Cyclohexanone • • • • • . • • • • • 37 (b) I-Rexene. • • • . • . • • • • • 37 (c) Styrene • . • • • . • . • • . • 38 (d) Acetic Acid • • . • • • • • • • • ei .• 38 (e) Butyric Acid. • • • • • • • • • • • • 39 (f) Caproic Acid. • • • • • • • • • • • • 39 (g) Caprylic Acid • • • . • • • . • . • 40 (h) Capric Acid • • • • .. • . • . • • . 40 (i) Laurie Acid • • . • • • . • • • . 40 (j) Stearic Acid. • • • • . • • . • • • • 41 (k) (3 -Alanine. • • • • • • • ..'. • . • • 41 (1) Phenylalanine • • • . • • . • • • • 41 (m) Glutaric Acid • • • • • • . • • . • • 42 (n) Ethyl Acetate • • • • • • • • • • • • 42 (o) Butyl Butyrate. • • • • . • • . • 42 (p) Ethyl Benzoate. • • • • • . • • • • . 43 (q) Rydrazobenzene. • • • • . • . • • • • 43 (r) Azobenzene. • • . • • • • • . • • • • 43 (s) Acetamide . • • • • • • . • • . • • . 43 (t) Acetanilide . • . • • • . • • • . • . 44 (u) N-Ethylacetanilide. • • • • . • . • 44 4. Hydrogenations With Rhenium Trichloride Derived Catalysts • • . • • • • • . • • • 44 (a) 2-Butanone. • • • • • • • • • • • • • 44 (b) 3-Reptanone • . • • . • . • • • • . 44 (c) 2-0ctanone. • . • • • • • • . • • . • 45 (d) 5-Hexene-2-one. • • • • . • • • • • . 45 (e) Cyclohexaneone. • • . • • • • • . 45 (f) Crotonaldehyd'3• • • • • • • . • • • • 46 (g) I-Rexene. • • • • • • . • • • • • • • 46 (h) Cyclohexene . • . • • . • • • • . • 46 (i) Styrene • . • . • . • . .. • . • • . 46 (j) Benzene • . • . • . • 46 (k) Nitrobenzene. • . • . • • • • 47 (1) Acetic Acid • • . • • • . • • • • • • 47 (m) Butyric Acid. .. 47 . • • . • • ~• . (n) Ethyl Acetate • • • • • . • • . • . 47 IV. DISCUSSION. • • . • • • • • • • • • • • . ., . 48 A. Catalyst Preparation and Properties. • • • • . • 48 1. Rhenium Trioxide. • • • . • . • • . • . • 48 2. Rhenium Heptoxide Derived Catalysts . • • • 49 3. Rhenium Trichloride • . • . • 50 B. Analysis of Catalysts. • • • . • . • . • . • . 50 1. Ultimate Analysis • • • . • . • . • 50 2. Oxidation State Determination • . • . • 52 c. Analysis of Hydrogenation Products • . • . • 53 D. Hydrogenations . • . • 53 vi pace 1. Rhenium Trioxide Derived Catalysts ••••• 53 2. Rhenium Heptoxide Derived Catalysts Re- duced Ex Situ in Acetic Acid •••••••• 60 3. RheniumHeptoxide Derived Catalysts Re- duced In Situ ••••••••••••••• 60 4. RheniumTricliloride Catalysts Derived In Situ •••••••••••••••••• 68 E. A ComparI'soii of Rhenium Trioxide, Rhenium Heptoxide and Rhenium Trichloride Catalysts ••• 71 F. Comparison of the Rhenium Derived Catalysts in the Reduction of Selected Substrates ••••• 76 G. A Comparison of the Catalysts Used in This Study With Some of the "Standard" Catalysts ••• 83 V. SUMMARY•••• • • . • • • . 89 VI. BIBLIOGRAPHY• • • • • • . • • • • • • . • • • • 91 vii LIST OF TABLESAND FIGURES Table page I. Hydrogenations Using Rhenium Trioxide Derived Catalysts Reduced --In Situ 54 II+ Hydrogenations Using Rhenium Heptoxide Derived Catalysts Reduced Ex Situ in Acetic Acid 61 III. Hydrogenations Using-- Rhenium Heptoxide Derived Catalysts Reduced~ ill,!! 62 IV. Hydrogenations Using Rhenium Trichloride Derived Catalysts Reduced .--In Situ 69 v. Comparison of Rhenium Trioxide, Rhenium Heptoxide and Rhenium Trichloride Catalysts 72 VI. Comparison 0£ the Rhenium Derived Catalysts in the Hydrogenation of Selected Substrates 77 VII. Comparison of Rhenium Trioxide, Rhenium Heptoxide and Rhenium Trichloride with Some of the "Standard" Catalysts in the Hydrogenation of Selected Substrates 84 Figure I. The Effect of Water on the Reduction of Carboxylic Acids with Rhenium
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