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Higher Alcohols in the Alcoholic Distillation from Fermented Cane Molasses

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Higher Alcohols in the Alcoholic Distillation from Fermented Cane Molasses Louisiana State University LSU Digital Commons LSU Historical Dissertations and Theses Graduate School 1956 Higher Alcohols in the Alcoholic Distillation From Fermented Cane Molasses. Herminio M. Brau Louisiana State University and Agricultural & Mechanical College Follow this and additional works at: https://digitalcommons.lsu.edu/gradschool_disstheses Recommended Citation Brau, Herminio M., "Higher Alcohols in the Alcoholic Distillation From Fermented Cane Molasses." (1956). LSU Historical Dissertations and Theses. 166. https://digitalcommons.lsu.edu/gradschool_disstheses/166 This Dissertation 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 Historical Dissertations and Theses by an authorized administrator of LSU Digital Commons. For more information, please contact [email protected]. HIGHER ALCOHOLS IN THE ALCOHOLIC DISTILLATION FROM FERMENTED CANE MOLASSES A Dissertation 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 Doctor of Philosophy in The Department of Chemical Engineering by Herminio M. Brau B.S., University of Puerto Rico, 1944 M.Chera.Eng., New York U n iv e rsity , 1949 Ju ly , 1956 ACKNOWLEDGEMENT The author wishes to express Ms sincere gratitude to Dr. Arthur G. Keller for his sympathetic guidance, advice and interest in this work, to Mr. Victor Rodrigues Benites, Technical Director of the Run\ Pilot Plant of the AgricJtLtural Experimental Station of the University of Puerto Rico for valuable suggestions and advice during the experi­ mental phase of this research, and to the Agricultural Experimental Station of the University' of Puerto Rico whose financial assistance made th is work p o ssib le . TABLE OF CONTENTS Page ACKNOWLEDGEMENT ................................................................................................... i i ABSTRACT.................................................................................................................... x i CHAPTERS I . ORIGIN AND COMPOSITION OF FUSEL OIL............................................ 1 General Considerations and Definition of Terms .... I Constituents of Fusel Oil . 3 Origin of Fusel Oil ......................................................................... 6 Reaction Mechanism for the Deamination of Amino Acids. 17 Composition of Fusel Oil From Different Substrates . 19 Yields of Fusel Oil From Different Raw Materials . 21 Fusel Oil Content in Alcoholic Beverages .......................... 22 I I . COMMERCIAL USES OF FUSEL OIL ....................................... 24 Specifications for Fusel Oil and Am}-! Alcohol .................. 25 Production and Imports of Fusel Oil and Amyl Alcohol . 27 Uses of Amyl Alcohols and Fusel Oil. .......... 28 I I I . ANALYTICAL METHODS FOR THE DETERMINATION OF FUSEL OIL. 31 Rose-Herzfeld Volumetric Method. ........... 32 Allen-Marquardt Volumetric Method. ...................... 34 Mohler-Rocqucs Colorimetric Method . .............................. 37 Komarowsky-Fellenberg Colorimetric Method .......................... 40 Modifications to Komarovsky's Method ..................... 43 Miscellaneous Methods ..................................................................... 46 IV. EFFECT OF THE PRESENCE OF DIFFERENT CONCENTRATIONS OF FUSEL OIL ON THE DETERMINATION OF ALCOHOL BY PICNOMETER, REFRACTOMETER AND HYDROMETER ......................... 4S V. SEPARATION AND PURIFICATION OF FUSEL OIL DURING THE DISTILLATION PHASE OF THE PROCESS OF MANUFACTURE .... 56 Objectives of the D istillation Process ........ 5S Intermittent D istillation Processes, ......... 61 Continuous D istillation Processes ........................................... 67 Behavior of Fusel Oil in the Operation of the P u rify in g Column. .................. 72 Behavior of Fusel Oil in the Operation of the Rectifying Column ............................................... 82 Purification of the Fusel Oil Take-off ..................... 89 VI * AUTOMATIC CONTROLS IN THE ALCOHOLIC DISTILLATION .... 94 Quantity Control Systems ..................... 102 Composition Control Systems .............................................................109 i i i Page Modifications Developed in This Work Composition Control Sj'stem III ......... 119 Composition Control System IV ..................... 123 VII i EXPERIMENTS DATA ON FUSEL OIL DISTRIBUTION IN THE RECTIFYING COLUMN UNDER DIFFERENT OPERATING CONDITIONS......................... 134 Experimental Procedure and Equipment Utilised . 134 R esu lts .......................................................................................142 Conclusions .............................................................................. 151 V III. COMPILATION OF EQUILIBRIUM DATA FOR THE SYSTEM ETHANOL-WATER AT ATMOSPHERIC PRESSURE .............................. 159 BIBLIOCRAPHY................................................................................. 162 Origin and Composition of Fusel O il ............................. 163 Commercial Uses of Fusel O il ......................................................... 173 Analytical Methods for the Determination of Fusel Oil . 174 Separation and Purification of Fusel Oil During D istillation ............................. 179 Automatic Controls in the Alcoholic D istillation .............. 183 Compilation of Equilibrium Data for the System Ethanol- Water at Atmospheric Pressure .....................................................1S5 APPENDIX - TABLES OF EXPERIMENTAL DATA........................................ 187 AUTOBIOGRAPHY................................................................................................259 iv LIST OF TABLES Page TEXT 1. Composition of Fusel Oil From Different Origins .... 20 2. Yields of Fusel Oil From Different Raw Materials. 21 3. Fusel Oil Content in Alcoholic Beverages. ....... 23 4. Production and Imports of Amyl Alcohol and Fusel Oil, . 27 5. Allocations of Amyl Alcohols From April 1—June 30, 1935 ......................'............................................................................ 2S 6. Fusel Oil and Alcohol Distribution by Plates of the P u rify in g Column ......................................................................... 78 7. Fusel Oil and Alcohol Distribution by Plates of the P u rify in g Column ................................................................ 79 8. Operating Conditions in the Rectifying Column in the Various Experiments Conducted at Different Reflire Ratios and Feed Compositions ............................. 139 9. Location of Plate of Maximum Fusel Oil Concentration Under Different Operating Conditions ........ 150 10. Fusel Oil Content in Main Product Under Different Operating Conditions . .......................................... 151 : 11. Fusel Oil Content in Top Plate of the Rectifying Column Under Different Operating Conditions ........ 151 12. Apparent Alcohol Content in the Plate of Maximum Fusel Oil Concentration ..................... 153 APPENDIX I. Experimental Data on the Effect of the Presence of Different Concentrations of Fusel Oil on the Determination of Alcohol by Picnoineter, Refrac- tomcter and Hydrometer ................................. 188 II-XV. Experimental Data Obtained in the Studies on Automatic Controls in the Alcoholic D istillation. 190 v Page XVI-LX. Experimental Data on Fusel Oil and Alcohol D istri­ bution by P la te s o f the R ectify in g Colismi Under Different Operating Conditions ................................... 204 LXI. Equilibrium Compositions for the System Ethanol- Water at Atmospheric Pressure in Terms of Per Cent by Weightj Mol Fraction and Per Cent by Volume a t bO°F and 20°C. ....................................... 249 v i LIST OK FIGURES Page 1. Effect of Presence of Fusel Oil on the Determination of Alcohol by the Picnomcter and Hydrometer Methods . 54 2. Effect of Presence of Fusel Oil on the Determination of Alcohol by the Refractometer Method. .......................... 56 / v i i LIST OF DRAWINGS Page DRAWING NUMBER 1. Distillation Flow Sheet ............... 68 2. Quantify Control System I ........................................................... 103 3. Quantity Control System II ........................................106 4. Quantity Control System III ....................................110 5. Composition Control System I. ..... 112 5A. Composition Control System l‘A ...........................................114 6. Composition Control System I I ...» 115 6A. Composition Control System IIA ...........................................117 7. Composition Control System III. ........... l'2l 8. Composition Control S 3'stein IV ........... 128 9. Flow Diagram and Instrumentation of Rectifying Column ................. 138 v i i i ABSTRACT Fusel oil is the name given collectively to a mixture of alcohols higher in molecular weight than ethanol, obtained as by-products in the alcoholic fermentation industries. Iso-amyl, active-amyl, iso-butyl and n-propyl alcohols are generally the main constituents of fusel oil with n-amyl, n-butyl and iso-propyl alcohols generally present in lesser amounts. In addition, minute amounts of a wide variety of organic sub­ stances appear as impurities in the fusel oil by-product. The main constituent alcohols of fusel oil arc derived from amino acids present in the mash and formed by autolytic breakdown of the pro­ teins of the cells themselves. The origin of n-butyl and iso-propyl alcohols
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