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Fractionation of Lignin Derived Compounds from Thermochemically Processed Lignin Towards Antimicrobial Properties

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Fractionation of Lignin Derived Compounds from Thermochemically Processed Lignin Towards Antimicrobial Properties University of Kentucky UKnowledge Theses and Dissertations--Biosystems and Agricultural Engineering Biosystems and Agricultural Engineering 2018 FRACTIONATION OF LIGNIN DERIVED COMPOUNDS FROM THERMOCHEMICALLY PROCESSED LIGNIN TOWARDS ANTIMICROBIAL PROPERTIES Luke A. Dodge University of Kentucky, [email protected] Digital Object Identifier: https://doi.org/10.13023/ETD.2018.130 Right click to open a feedback form in a new tab to let us know how this document benefits ou.y Recommended Citation Dodge, Luke A., "FRACTIONATION OF LIGNIN DERIVED COMPOUNDS FROM THERMOCHEMICALLY PROCESSED LIGNIN TOWARDS ANTIMICROBIAL PROPERTIES" (2018). Theses and Dissertations-- Biosystems and Agricultural Engineering. 54. https://uknowledge.uky.edu/bae_etds/54 This Master's Thesis is brought to you for free and open access by the Biosystems and Agricultural Engineering at UKnowledge. It has been accepted for inclusion in Theses and Dissertations--Biosystems and Agricultural Engineering by an authorized administrator of UKnowledge. For more information, please contact [email protected]. STUDENT AGREEMENT: I represent that my thesis or dissertation and abstract are my original work. Proper attribution has been given to all outside sources. I understand that I am solely responsible for obtaining any needed copyright permissions. I have obtained needed written permission statement(s) from the owner(s) of each third-party copyrighted matter to be included in my work, allowing electronic distribution (if such use is not permitted by the fair use doctrine) which will be submitted to UKnowledge as Additional File. I hereby grant to The University of Kentucky and its agents the irrevocable, non-exclusive, and royalty-free license to archive and make accessible my work in whole or in part in all forms of media, now or hereafter known. I agree that the document mentioned above may be made available immediately for worldwide access unless an embargo applies. I retain all other ownership rights to the copyright of my work. I also retain the right to use in future works (such as articles or books) all or part of my work. I understand that I am free to register the copyright to my work. REVIEW, APPROVAL AND ACCEPTANCE The document mentioned above has been reviewed and accepted by the student’s advisor, on behalf of the advisory committee, and by the Director of Graduate Studies (DGS), on behalf of the program; we verify that this is the final, approved version of the student’s thesis including all changes required by the advisory committee. The undersigned agree to abide by the statements above. Luke A. Dodge, Student Dr. Jian Shi, Major Professor Dr. Donald Colliver, Director of Graduate Studies FRACTIONATION OF LIGNIN DERIVED COMPOUNDS FROM THERMOCHEMICALLY PROCESSED LIGNIN TOWARDS ANTIMICROBIAL PROPERTIES ____________________________________ THESIS _____________________________________ A thesis submitted in partial fulfillment of the requirements for the degree of Master of Science in Biosystems and Agricultural Engineering in the College of Engineering at the University of Kentucky By: Luke Dodge Lexington, Kentucky Director: Dr. Jian Shi, Assistant Professor of Biosystems and Agricultural Engineering Department Lexington, Kentucky 2018 Copyright © Luke Anthony Dodge 2018 ABSTRACT OF THESIS FRACTIONATION OF LIGNIN DERIVED COMPOUNDS FROM THERMOCHEMICALLY PROCESSED LIGNIN TOWARDS ANTIMICROBIAL PROPERTIES The overuse of antibiotics in agriculture is an emerging concern, due to their potential detrimental impact to the environment. This study focuses on exploring antimicrobial properties of lignin derived compounds. Lignin is of interest as a feedstock to replacing some petroleum-based chemicals and products because it is the most abundant source of renewable aromatic compounds on the planet. Two lignin rich streams, residues from the enzymatic hydrolysis of dilute acid and alkaline pretreated corn stover, were decomposed via pyrolysis and hydrogenolysis, respectively. The resulting liquid oils were subjected to sequential extractions using a series of solvents with different polarities. Chemical compositions of the extracted fractions were characterized through HPLC and GC/MS. These extracted compounds were screened against Saccharomyces cerevisiae (S. cerevisiae), Escherichia coli, and Lactobacillus amylovorus for antimicrobial properties. Six lignin model monomers: guaiacol, vanillin, vanillic acid, syringaldehyde, 2,6-dimethoxyphenol, and syringic acid were compared to the oils and extracted fractions for antimicrobial properties. Development of lignin- derived chemicals with antimicrobial properties could provide a novel use for this underutilized natural resource. KEYWORDS: lignin, pyrolysis, hydrogenolysis, liquid-liquid extraction, antimicrobial Luke Dodge April 26, 2018 FRACTIONATION OF LIGNIN DERIVED COMPOUNDS FROM THERMOCHEMICALLY PROCESSED LIGNIN TOWARDS ANTIMICROBIAL PROPERTIES By Luke Anthony Dodge Dr. Jian Shi Director of Thesis Dr. Donald Colliver Director of Graduate Studies April 26, 2018 Acknowledgments I am extremely grateful for the people who helped me throughout my research. I first want to thank my graduate advisor Dr. Jian Shi for his support through my graduate career at the University of Kentucky. I would like to extend a thank you to my other committee members Drs. Sue Nokes and Barbara Knutson for their insightful comments and guidance on my research project. I would like to thank Dr. Xiaowen Chen at NREL for providing the lignin samples and Dr. Lalitendu Das for helping with the GC/MS and GPC analysis. I also like to thank Dr. Dorin Boldor and Dr. Pranjali Muley from LSU for their helping on with the pyrolysis. I want to thank my mom and dad for all they have done to help me succeed during my graduate career. Your love and endless support was the motivation I needed to help me through this process. I would like to acknowledge the National Science Foundation under Cooperative Agreement No. 1355438 and 1632854 and the National Institute of Food and Agriculture, U.S. Department of Agriculture, Hatch-Multistate project under accession number 1003563 for supporting this research. iii TABLE OF CONTENTS Acknowledgments.............................................................................................................. iii LIST OF TABLES ............................................................................................................. vi LIST OF FIGURES .......................................................................................................... vii CHAPTER 1: INTRODUCTION ........................................................................................1 Introduction ......................................................................................................................1 1.1 Literature Review .......................................................................................................1 1.1.2 Lignin...................................................................................................................1 1.1.3 Thermochemical Lignin Decomposition .............................................................2 1.1.4 Sequential Extraction ...........................................................................................4 1.1.5 Lignin Derived Antimicrobials ............................................................................5 1.1.6 Applications in a Biorefinery ..............................................................................9 1.2 Research Motivations ...............................................................................................10 1.3 Objectives .................................................................................................................11 1.4 Research Approach and Research Questions ...........................................................11 1.4.1 Research Approach: ...........................................................................................11 1.4.2 Research Questions: ..........................................................................................12 CHAPTER 2: FRACTIONATION AND CHARACTERIZATION OF LIGNIN DERIVED COMPOUNDS FROM THERMOCHEMICALLY PROCESSED LIGNIN .13 Introduction ....................................................................................................................13 2.1. Experimental ...........................................................................................................13 2.1.1 Materials ............................................................................................................13 2.1.2 Lignin Sample Preparation ................................................................................13 2.1.3 Pyrolysis Protocol ..............................................................................................14 2.1.4 Catalytic Transfer-Hydrogenolysis (CTH) Protocol .........................................15 2.1.5 Gas Chromatography-Mass Spectrometry (GC/MS) Protocol ..........................16 2.1.6 Gel Permeation Chromatography (GPC) Protocol ............................................16 2.1.7 Sequential Extraction Protocol ..........................................................................17 2.1.8 Fourier-transform Infrared Spectroscopy (FTIR) ..............................................19 2.1.9 Statistical Analysis ............................................................................................19 2.2. Results and Discussion ............................................................................................20
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