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Screening of Catalysts for the Subcritical Water Depolymerization of Lignin

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Screening of Catalysts for the Subcritical Water Depolymerization of Lignin South Dakota State University Open PRAIRIE: Open Public Research Access Institutional Repository and Information Exchange Electronic Theses and Dissertations 2020 Screening of Catalysts for the Subcritical Water Depolymerization of Lignin Balawanthrao Jadhav South Dakota State University Follow this and additional works at: https://openprairie.sdstate.edu/etd Part of the Chemistry Commons Recommended Citation Jadhav, Balawanthrao, "Screening of Catalysts for the Subcritical Water Depolymerization of Lignin" (2020). Electronic Theses and Dissertations. 4993. https://openprairie.sdstate.edu/etd/4993 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 Electronic 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]. SCREENING OF CATALYSTS FOR THE SUBCRITICAL WATER DEPOLYMERIZATION OF LIGNIN BY BALAWANTHRAO JADHAV A dissertation submitted in partial fulfilment of the requirements for the Doctor of Philosophy Major in Chemistry South Dakota State University 2020 ii DISSERTATION ACCEPTANCE PAGE Balawanthrao Jadhav This dissertation is approved as a creditable and independent investigation by a candidate for the Doctor of Philosophy degree and is acceptable for meeting the dissertation requirements for this degree. Acceptance of this does not imply that the conclusions reached by the candidate are necessarily the conclusions of the major department. Douglas Raynie Advisor Date Douglas Raynie Department Head Date Nicole Lounsbery, PhD Director, Graduate School Date iii ACKNOWLEDGEMENTS I express my deepest gratitude to my advisor, Dr. Douglas E. Raynie, for his continuous support, constant encouragement, and guidance throughout this journey. I thank him for being with me to improve my knowledge and research skills in the field of science through his valuable suggestions. He is not only a research advisor but also a kind nature human in society. He helped me in all difficulty situations in this journey. He is always welcoming everyone with his beautiful smile in the department. I thank my advisory committee members, Dr. Fathi Halaweish, Dr. Cheng Zhang, and Dr. William J. Wood for their invaluable guidance and feedback throughout my graduate study. I extend my sincere thanks to Dr. Ronald Hirko for his motivation and guidance to develop the teaching skills. I would like to thank the Department of Chemistry and Biochemistry, South Dakota State University, staff, and fellow co-workers for supporting and helping me to achieve this milestone in my life. I would like to thank SDSU and Brookings Community to provide us safest environment throughout this journey. I am thankful to the Indian Student Association to allowed me to serve as the President of the Indian Student Association. I am thankful to International Student Affairs to gave me the opportunity to help the international students during the COVID-19 pandemic. I appreciate my lambastes Ranen Roy, Ahsan Ahmed, Shiksha Subedi, Sajjadur Rahman, and Shanmugapriya Dharmarajan for their academic and personal support. I am grateful to Nancy Awasthi, Prachi Pahariya, Kanya Maji, Abhijit Maji, and Ramu K Dasarath for being with us always to support us in every situation like a family member. iv My heartful thanks to my beloved friend Dr. Darmakkolla Srikarrao for his encouragement, motivation, and support to come to United States to pursue my Doctorate. I am greatly indebted to my parents Madhav Rao Jadhav and Rathna Bai Jadhav for their love, blessings, support, prayers, and sacrifice throughout my education. I extend my acknowledgement to my brothers Sainath Jadhav and Vilas Rao Jadhav for their continuous support and encouragement. My acknowledgements to my family members, relatives, and well-wishers for their blessings and encouragement. I express my thanks to my wife Pranitha Jadhav, for being with me always for supporting, caring, and helping me to reach this milestone. My lovely daughter, Sriprajwala Jadhav, you are my strength in this chapter and your presence made every moment is joyful. This study was supported by the National Science Foundation EPSCoR Track II Dakota BioCon project for the North and South Dakota (Grant Nos. IIA-1355466 and IIA- 1330842). Thanks to everyone, who supported me directly, and indirectly throughout this journey. v TABLE OF CONTENT LIST OF ABBREVIATIONS ………………………………………………………. ix LIST OF FIGURES …………………………………………………………………. x LIST OF TABLES …………………………………………………………………. xvi ABSTRACT ………………………………………………………………………… xx CHAPTER ONE: INTRODUCTION AND BACKGROUND …………………. 1 1.1. Introduction ……………………………………………………………….1 1.1.1. Biomass …………………………………………………………1 1.2. Lignocellulosic Biomass ………………………………………………… 2 1.2.1. Introduction ……………………………………………………. 2 1.3. Lignin ……………………………………………………………………. 3 1.3.1. Introduction ……………………………………………………. 3 1.3.2. Lignin structure …………………………………………………3 1.3.3. Lignin sources …………………………………………………. 5 1.4. Lignin monomers applications …………………………………………... 6 1.5. Lignin Extraction ………………………………………………………….6 1.6. Depolymerization of Lignin ………………………………………………10 1.7. Subcritical water ………………………………………………………….12 1.7.1. Introduction ……………………………………………………. 12 1.7.2. Applications of Subcritical water ……………………………… 13 vi CHAPTER TWO: CATALYST SCREENING FOR THE DEPOLYMERIZATION OF LIGNIN IN THE PRESENCE OF SUBCRITICAL WATER …………….24 2.1. Introduction ……………………………………………………………. 24 2.2. Experimental ……………………………………………………………27 2.2.1. Materials and Catalysts ……………………………………….27 2.2.2. Hydrothermal Conversion Process ……………………………28 2.2.3. Separation and Extraction of Phenolic monomers ……………29 2.2.4. GC-MS Analysis ……………………………………………...29 2.3. Results and Discussion …………………………………………………29 2.3.1. Product Analysis and Quantification ………………………….29 2.4. Role of Subcritical water and Catalysts in depolymerization of alkali Lignin…………………………………………………………………...58 2.5. The possible pathways and mechanism of Alkali lignin in the presence of subcritical water and catalysts………………………………………60 2.6. Summary ……………………………………………………………….62 2.7. Conclusion ……………………………………………………………...63 vii CHAPTER THREE: OPTIMIZATION OF REACTION CONDITIONS FOR THE DEPOLYMERIZATION OF ALKALI LIGNIN IN THE PRESENCE OF SUBCRITICAL WATER AND CATALYST …………………………………...65 3.1. Introduction ……………………………………………………………. 65 3.2. Experimental ……………………………………………………………67 3.2.1. Materials ……………………………………………………….67 3.2.2. Method …………………………………………………………67 3.2.3. GC-MS analysis ……………………………………………….68 3.3. Results and Discussion ………………………………………………...68 3.3.1. Identification of Products and Quantification …………………68 3.4. Summary ………………………………………………………………76 3.5. Conclusion …………………………………………………………….77 CHAPTER FOUR: EXTRACTION AND DEPOLYMERIZATION OF LIGNIN FROM PINE SAWDUST AND PISTACHIO SHELLS BIOMASS…………. 78 4.1. Introduction …………………………………………………………. 78 4.2. Materials ……………………………………………………………...80 4.3. Experimental procedure ………………………………………………80 4.3.1. Extraction of lignin from Pine sawdust and Pistachio shells….80 4..3.2. Sample Preparation…………………………………………...81 viii 4.3.3. Experimental setup ………………………………………….82 4.3.4. Depolymerization of lignin from Pistachio Shells …………. 83 4.4. Results and Discussion ……………………………………………...84 4.4.1. Characterization of extracted lignin ……………………...84 4.4.1.1. FT-IR spectroscopy …………………………………….84 4.4.1.2. 1H NMR spectroscopy ………………………………….86 4.4.1.3. Thermogravimetric analysis (TGA) ……………………88 4.4.1.4. Identification of phenolic monomers using GC-MS……89 4.5. Conclusion ………………………………………………………....92 CHAPTER FIVE: CONCLUSIONS AND FUTURE WORK ………………. 93 REFERENCES …………………………………………………………………. 96 ix ABBREVIATIONS AL……………………………………… Alkali Lignin SCW……………………………………. Subcritical Water ASE……………………………………. Accelerated Solvent Extraction MIK……………………………………. Methyl Isobutyl Ketone TGA…………………………………… Thermogravimetric Analysis GC-MS………………………………… Gas Chromatography-Mass Spectrometry FT-IR…………………………………... Fourier Transformation Infrared Spectroscopy ([bmim][Cl]) …………………………... 1-butyl-3-methylimidazolium chloride OPB …………………………………... Oil Palm Biomass ScCO2 ………………………………… Supercritical Carbon dioxide [MMIM]-[MeSO4] ……………………… ….1,3-dimethylimidazolium methyl sulfate DCM …………………………………….......Dichloromethane BSA …………………………………………Bovine Serum Albumin LC-MS/MS ………………………………… Liquid chromatography-tandem mass spectrometry AA ……………………………………….... Anhydrous Ammonia CSS……………………………………. Coriandrum Sativum Seeds PS …………………………………………. Pistachio Shells AADESs ………………………………Amino acid deep eutectic solvents HDO …………………………………. Hydrodeoxygenation HTL …………………………………...Hydrothermal Liquefaction [BMIM]CF3SO3] ………………………1-butyl-3-methylimidazolium trifluoromethanesulfonate x LIST OF FIGURES Figure 1.1. Structure of Lignocellulosic biomass and different types of components …………………………………………………………………………….2 Figure 1.2. The Complex structure of lignin ………………………………………….5 Figure 1.3. Phase diagram of water representing sub-and supercritical region …………………………………………………………………………………...13 Figure 2.1. Phenolic monomers of the lignin ………………………………………… 25 Figure 2.2. Stepwise process for the depolymerization of alkali lignin in the presence of subcritical water and different types of Catalysts……………………………………... 28 Figure 2.3. Standard calibration curves of six phenolic monomers……………………30 Figure 2.4. GC-MS chromatogram of phenolic monomers from the alkali lignin in
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