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Deep Eutectic Solvents Synthesis, Characterization and Applications in Pretreatment of Lignocellulosic Biomass Ganesh Degam South Dakota State University

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Deep Eutectic Solvents Synthesis, Characterization and Applications in Pretreatment of Lignocellulosic Biomass Ganesh Degam South Dakota State University South Dakota State University Open PRAIRIE: Open Public Research Access Institutional Repository and Information Exchange Theses and Dissertations 2017 Deep Eutectic Solvents Synthesis, Characterization and Applications in Pretreatment of Lignocellulosic Biomass Ganesh Degam South Dakota State University Follow this and additional works at: http://openprairie.sdstate.edu/etd Part of the Chemistry Commons Recommended Citation Degam, Ganesh, "Deep Eutectic Solvents Synthesis, Characterization and Applications in Pretreatment of Lignocellulosic Biomass" (2017). Theses and Dissertations. 1156. http://openprairie.sdstate.edu/etd/1156 This Dissertation - Open Access is brought to you for free and open access by Open PRAIRIE: Open Public Research Access Institutional Repository and Information Exchange. It has been accepted for inclusion in Theses and Dissertations by an authorized administrator of Open PRAIRIE: Open Public Research Access Institutional Repository and Information Exchange. For more information, please contact [email protected]. DEEP EUTECTIC SOLVENTS SYNTHESIS, CHARACTERIZATION AND APPLICATIONS IN PRETREATMENT OF LIGNOCELLULOSIC BIOMASS BY GANESH DEGAM A dissertation submitted in partial fulfillment of the requirements for the Doctor of Philosophy Major in Chemistry South Dakota State University 2017 iii ACKNOWLEDGEMENTS There are literally a number of people involved in the fulfillment of this dissertation work. List they remain unnoticed. I would like to devote some space here to acknowledge their valuable contribution. I would like to express my gratitude to my advisor, Dr. Douglas E Raynie for sharing his vast knowledge in analytical chemistry and for his never-ending support and encouragement all through. His strong belief in science combined with a systematic approach, tremendous enthusiasm, and convivial criticism has been of great help and a real inspiration to me. I would like to thank the members of my graduate committee, Drs. Jihong Cole- Dai, Fathi Halaweish, and Francis Ting for their encouragement, useful comments, remarks, and engagement through the entire learning process. I extend my thanks to the graduate and undergraduate students of the green chemistry lab for their help and wholehearted support throughout my work. I find no words to express my thanks to my wife Nikitha Gundeti, who has encouraged and supported me through these tough times nothing could have been possible without her affection and encouragement. Last but not least I extend my sincere gratitude to Almighty for giving me this life and allow me to live in a wonderful world of green chemistry. This research was sponsored by the Army Research Laboratory and was accomplished under Cooperative Agreement Number W911NF-08-2-0024. The views iv and conclusions contained in this document are those of the authors and should not be interpreted as representing the official policies, either expressed or implied, of the Army Research Laboratory or the U.S. Government. The U.S. Government is authorized to reproduce and distribute reprints for Government purposes notwithstanding any copyright notation herein. v CONTENTS LIST OF FIGURES ...……………………………………………………………………xi LIST OF TABLES ……………………………………………………………………...xvi LIST OF EQUATIONS .………………………………………………………………xviii LIST OF ABBREVIATIONS ...………………………………………………………...xix ABSTRACT …………………………………………………………………………..xxiii 1 INTRODUCTION AND BACKGROUND ............................................................. 1 1.1 Problem Statement ............................................................................................... 1 1.2 Deep Eutectic Solvents ........................................................................................ 2 1.2.1 Definition .............................................................................................. 2 1.2.2 Classification ......................................................................................... 3 1.2.3 Type III Deep Eutectic Solvents ........................................................... 3 1.2.3.1 Choline Chloride ............................................................................ 6 1.2.3.2 Acetylcholine Chloride .................................................................. 7 1.2.3.3 Urea ................................................................................................ 7 1.2.3.4 Glycerol.......................................................................................... 8 1.2.4 Advantages ............................................................................................ 9 1.2.5 Number of Published References ........................................................ 10 1.2.6 Distribution of the Research Field ...................................................... 11 1.2.7 Applications ........................................................................................ 12 1.3 Lignocellulosic Biomass .................................................................................... 13 1.3.1 Biomass Pretreatment .......................................................................... 15 1.4 Justification of Study ......................................................................................... 17 vi 2 SYNTHESIS ............................................................................................................. 18 2.1 Introduction ........................................................................................................ 18 2.2 Experimental ...................................................................................................... 19 2.2.1 Materials .............................................................................................. 19 2.2.2 Methods ............................................................................................... 20 2.2.2.1 Thermal Treatment....................................................................... 20 2.2.2.2 Microwave Irradiation ................................................................. 21 2.2.2.3 Shaking Incubation ...................................................................... 21 2.2.2.4 Sonication .................................................................................... 21 2.2.2.5 Vortex Mixing .............................................................................. 21 2.2.2.6 Freeze Drying............................................................................... 22 2.2.2.7 Rotary Evaporator ........................................................................ 22 2.2.2.8 Karl Fisher Titration .................................................................... 22 2.2.2.9 Freezing Point Determination ...................................................... 22 2.2.2.10 FTIR Spectroscopy .................................................................... 23 2.2.2.11 1H NMR Spectroscopy ............................................................... 23 2.3 Results and Discussion....................................................................................... 23 2.3.1 Freezing Temperature (Tf) .................................................................. 25 2.3.2 FTIR Spectroscopy Analysis............................................................... 29 2.3.3 1H NMR Spectroscopy Analysis ......................................................... 32 2.4 Conclusions ........................................................................................................ 36 3 CHARACTERIZATION ........................................................................................ 37 3.1 Introduction ........................................................................................................ 37 vii 3.2 Experimental ...................................................................................................... 39 3.2.1 Materials .............................................................................................. 39 3.2.2 Methods ............................................................................................... 40 3.2.2.1 Synthesis ...................................................................................... 40 3.2.2.2 Water Content .............................................................................. 40 3.2.2.3 pH ................................................................................................. 40 3.2.2.4 Density ......................................................................................... 40 3.2.2.5 Refractive Index ........................................................................... 41 3.2.2.6 Surface Tension ........................................................................... 41 3.2.2.7 Octanol-Water Partition Coefficient ............................................ 41 3.2.2.8 Viscosity ...................................................................................... 42 3.2.2.9 Flammability ................................................................................ 42 3.2.2.10 Freezing Temperature ................................................................ 43 3.2.2.11 Decomposition Temperature ...................................................... 43 3.3 Results and Discussion....................................................................................... 43 3.3.1 Synthesis and Water Content .............................................................. 43 3.3.2 pH ........................................................................................................ 44 3.3.3 Density ...............................................................................................
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