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UNIVERSITY of CALIFORNIA Santa Barbara Catalytic Depolymerization of Native and Technical Lignin Into Phenolic Compounds Using N UNIVERSITY OF CALIFORNIA Santa Barbara Catalytic Depolymerization of Native and Technical Lignin into Phenolic Compounds Using Nickel Catalyst A dissertation submitted in partial satisfaction of the requirements for the degree Doctor of Philosophy in Chemistry by Hao Luo Committee in charge: Professor Mahdi M. Abu-Omar, Chair Professor Steven K. Buratto Professor Peter C. Ford Professor Susannah L. Scott June 2018 The dissertation of Hao Luo is approved. _____________________________________________ Mahdi M. Abu – Omar, Committee Chair _____________________________________________ Steven K. Buratto _____________________________________________ Peter C. Ford ____________________________________________ Susannah L. Scott May 2018 Catalytic Depolymerization of Native and Technical Lignin into Phenolic Compounds Using Nickel Catalyst Copyright © 2018 by Hao Luo iii ACKNOWLEDGEMENTS First of all, I would like to express the deepest appreciation to my family for all their support throughout my life, without whom this dissertation would not be possible. I would also like to thank my research advisor Prof. Mahdi Abu-Omar for his guidance and persistent help throughout my graduate studies. His excellent mentorship and dedication towards excellence in science has made a tremendous impact on my life. His encouragement both academically and spiritually guaranteed the success of my graduate research. In addition, I would like to thank all of the current and past group members of the Abu-Omar research group. Your help was one of the most important factors that allowed me to succeed as a researcher. I am grateful for the Center for Catalytic Conversion of Biomass to Biofuels (C3Bio) for all the interdisciplinary collaborations and technical support. iv VITA OF HAO LUO June 2018 EDUCATION Bachelor of Science in Chemistry, Purdue University, May 2013 Doctor of Philosophy in Chemistry, University of California, Santa Barbara, June 2018 PROFESSIONAL EMPLOYMENT 2013-2016: Research Assistant, Department of Chemistry, Purdue University 2016-2018: Research Assistant, Department of Chemistry and Biochemistry, University of California, Santa Barbara PUBLICATIONS Hao Luo and Mahdi M. Abu-Omar. “Lignin Extract and Catalytic Upgrading from Genetically Modified Poplar”. Green Chem. 2018, 20, 745-753. Hao Luo, Frederic A. Perras, Ximing Zhang, Nathan S. Mosier, Marek Pruski and Mahdi M. Abu-Omar. “Atomic-Level Structure Characterization of Biomass Pre- and Post- Lignin Treatment by Dynamic Nuclear Polarization-Enhanced Solid-State NMR”. J. Phys. Chem A. 2017, 121, 623-630. Hao Luo and Mahdi M. Abu-Omar. (2017). Chemicals from Lignin. In M. Abraham (Ed.), Encyclopedia of Sustainable Technologies (pp. 573-585). Elsevier. Fan Wang, Greg Michalski, Hao Luo and Marc Caffee. “Role of biological soil crusts in affecting soil evolution and salt geochemistry in hyper-arid Atacama Desert, Chile”. Geoderma. 2017, 307, 54-64 Hao Luo, Ian M. Klein, Yuan Jiang, Hanyu Zhu, Baoyuan Liu, Hilkka I. Kenttämaa and Mahdi M. Abu-Omar. “Total Utilization of Miscanthus Biomass, Lignin and Carbohydrates: Using Earth Abundant Ni/C Catalyst”. ACS Sustain. Chem. Eng. 2016, 4, 2316-2322. v Hanyu Zhu, Joann P. Max, Christopher L. Marcum, Hao Luo, Mahdi M. Abu-Omar and Hilkka I. Kenttämaa. “Identification of the Phenol Functionality in Deprotonated Monomeric and Dimeric Lignin Degradation Products via Tandem Mass Spectrometry Based on Ion-Molecule Reactions with Diethylmethoxyborane”. J. Am. Soc. Mass Spectrom. 2016, 27(11), 1813-1823. Fan Wang, Wensheng Ge, Hao Luo, Ji-Hye Seo, Greg Michalski, “Oxygen-17 anomaly in soil nitrate: A new precipitation proxy for desert landscapes”. Earth. Planet. Sci. Lett. 2016, 438, 103-111. FIELDS OF STUDY Major Field: Inorganic Chemistry Studies in Catalytic Conversion of Lignin with Professor Mahdi Abu-Omar vi ABSTRACT Catalytic Depolymerization of Native and Technical Lignin into Phenolic Compounds Using Nickel Catalyst by Hao Luo Increasing greenhouse gas emissions as well as a series of environmental issues caused by fossil fuels combustion have motivated the development of renewable energy sources. Nonfood lignocellulosic biomass is a promising renewable source for making liquid fuels and valuable chemicals, due to its high energy content stored by the biosphere. However, the efficient utilization of biomass has been significantly hindered by its recalcitrant nature. Herein, we have investigated the use of Ni/C for the catalytic depolymerization of native lignin in Miscanthus, a grassy biomass. Under optimized conditions, over 69% yield of select aromatic products were obtained from lignin. Carbohydrates remaining after lignin removal were recovered as a solid residue, which upon treatment with iron chloride produced useful platform chemicals (furfurals and levulinic acid). Understanding bond connectivity in biomass (between lignin and carbohydrates) advances the development and commercialization of more efficient catalytic methods for biomass utilization. To achieve this goal, Dynamic Nuclear Polarization (DNP) Enhance Solid State NMR (ssNMR) was used to probe the atomic level structure of biomass pre- and post- lignin treatment. Our results revealed an increase in the relative ratio of crystalline cellulose upon the catalytic depolymerization of lignin (CDL) using Ni/C catalyst. In parallel with direct catalysis of native lignin in raw biomass, organosolv pretreatment was used to produce sulfur-free technical lignin in high vii purity. Our study investigated the effect of biomass substrate and organosolv pretreatment methods on the isolated lignin towards further upgrading over a Ni/C catalyst. By comparing different solvents (acetic acid/formic acid, acetone and methanol) applied for lignin extraction, methanol was revealed to minimize the undesirable re- condensation of organosolv lignin. viii TABLE OF CONTENTS Chapter Ӏ. Introduction: Potential and Difficulties in Conversion of Lignin into Value- Added Compounds A. Abstract………………………………………………………………………..1 B. Lignin basics: structure and isolation…………………………………………1 1. Lignin structure: building blocks and interlinkages……………………….1 2. Lignin isolation technologies…………………………………………...…2 C. Lignin valorization: conversion into value-added materials…………………..6 1. Lignin utilization as power/fuel………………………………………...…8 2. Lignin utilization as macromolecules……………………………………12 3. Lignin utilization as monomer aromatics………………………………..15 D. Environmental Benefits from utilization of lignin……………………….…..18 E. Conclusion…………………………………………………………...………20 F. References……………………………………………………………………21 Chapter ӀI. Total Utilization of Miscanthus Biomass: by Using Earth Abundant Metal Catalysts A. Introduction……………………………………..…………………………….31 B. Catalytic depolymerization of lignin (CDL) in miscanthus biomass using Ni/C catalyst……………………………………………………………………...…32 C. Identification and quantification of aromatic products……………………….33 D. Composition analysis of carbohydrate residue……………………………….38 E. Upgrading of carbohydrate residue into platform chemicals using FeCl3……40 ix F. Conclusion…………………………………………………………...………..42 G. Supporting information……………………………………………………….43 1. Materials and methods…………………………………………….……..43 2. Instrumentation and chromatographic conditions………………………..45 H. References…………………………………………………………………….48 CHAPTER III. Atomic Level Structure Characterization of Biomass Pre- and Post- Lignin Treatment by Dynamic Nuclear Polarization-Enhanced Solid State NMR. A. Introduction…………………………………………………………………..52 B. Catalytic depolymerization of lignin (CDL) in gene mutant poplar species using Ni/C catalyst…………………………………………………………...54 C. DNP enhanced ssNMR analysis on biomass………………………………...59 1. Comparison of cellulose region in raw biomass and residue after CDL reaction………………………………………………………...…………59 2. Comparison of lignin region in gene mutant poplar substrates……..…...62 D. Conclusion…………………………………………………………………...67 E. Supporting information………………………………………………………67 1. Materials and methods…………………………………………………...67 2. Instrumentation and chromatographic conditions………………………..71 F. References………………………………………………………………...….74 CHAPTER IV. Lignin Extract and Catalytic Upgrading from Genetically Modified Poplar. x A. Introduction……………………………………………………………….….82 B. Organosolv extraction of lignin from poplar species…………………...……85 C. Two dimensional HSQC-NMR analysis of organosolv lignin……………....88 D. Catalytic depolymerization of organosolv lignin………………………...….93 E. Conclusions……………………………………………………………...….100 F. Supporting information………………………………………………...…...101 1. Materials and methods………………………………………………….101 2. Instrumentation and characterization conditions………………...……..104 G. References…………………………………………………………………..107 CHAPTER V. Bio-based Epoxy Resin through the Curing of Surface Modified Cellulose with Epoxy Monomer Derived from Biomass. A. Introduction……………………………………………………………...….113 B. Surface modification of cellulose from organosolv extraction of poplar biomass……………………………………………………………………..116 C. Curing of surface modified cellulose with epoxide monomer……………...123 D. Conclusions and future work………………………………………...……..128 E. Supporting information………………………………………………...…...130 1. Materials and methods…………………………………………...……..130 2. Instrumentation and characterization conditions………………...……..133 F. References…………………………………………………………………..135 xi Chapter Ӏ. Introduction: Potential and Difficulties in Conversion of Lignin into Value-Added Compounds A. Abstract Increasing global energy consumption and environmental issues resulting from fossil fuel combustion
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