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ABSTRACT DE LA CRUZ, FLORENTINO BANAAG. Fate and Reactivity of Lignin in Municipal Solid Waste

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ABSTRACT DE LA CRUZ, FLORENTINO BANAAG. Fate and Reactivity of Lignin in Municipal Solid Waste ABSTRACT DE LA CRUZ, FLORENTINO BANAAG. Fate and Reactivity of Lignin in Municipal Solid Waste (MSW) Landfill. (Under the direction of Dr. Morton A. Barlaz). More than 50% of the 149 million metric tons of municipal solid waste (MSW) landfilled in the U.S. annually are derived from lignocellulosic materials (e.g. food and yard waste, wood, and pulp and paper products). As lignin is approximately 15% of residential solid waste, understanding its behavior during anaerobic decomposition in landfills is important for a complete description of carbon decomposition and storage in landfills. The overall objective of this dissertation was to use lignin in characterizing the decomposition of lignocellulose during anaerobic decomposition. This document is divided in three major sections to address (1) work to explore CuO oxidation as an alternative analytical method to improve quantification of lignin; (2) use of CuO lignin monomers as molecular markers to quantitatively estimate the amount of lignocellulose in mixed samples and; (3) to evaluate the chemical transformations of lignin during mesophilic and thermophilic anaerobic decomposition. To evaluate the feasibility of CuO oxidation as an alternate method to quantify lignin, experiments were conducted to evaluate potential for some common components of MSW to interfere with the CuO oxidation. Results showed the analysis of lignin phenols can be simplified by omission of the liquid – liquid extraction step traditionally employed as a purification step for subsequent GC/MS analysis. The study also showed that plastics, metals and lipophilic extractives do not affect CuO lignin in mixed MSW. It was also demonstrated the CuO lignin of ball-milled samples were not significantly different when compared to the CuO lignin of samples ground to pass a 60 mesh screen in a Wiley mill. Application of CuO oxidation of lignin on excavated landfill samples showed that similar conclusions can be obtained by using the traditional indicator of decomposition (Cellulose [Cel] + Hemicellulose[H])/Klason Lignin [KL]) and a new ratio based on sum of eight phenolic monomers (Λ8) from CuO oxidation (Cel+H)/Λ8. (Cel+H)/Λ8 in theory is more robust parameter in samples that may contain interferences as it is based on lignin specific measure. However, further study is necessary to explore the sensitivity and efficacy of (Cel+H)/Λ8 as a metric for the extent of MSW decomposition. To evaluate the applicability of CuO oxidation to estimate lignocellulose composition, end member mixing model was developed and calibrated using data from 93 different species of hardwood (HW), softwood (SW), leaves and grasses (LG) and needles (GN). Relatively accurate predictions were demonstrated in pure tissues. Poor predictions of GN in synthetic mixtures could be attributed to the deviation of CuO lignin of the selected end-members used formulating the synthetic mixtures from the mean value which was used in model development. Application of the model to estimate composition of landfill samples showed that majority of samples are comprised of HW and SW or pulp derived from these materials. To look for evidence of chemical transformations of lignin under mesophilic and thermophilic anaerobic conditions, Hardwood (HW), softwood (SW), grass and old newsprint (ONP) were decomposed in the laboratory and were analyzed both by chemical degradation and spectroscopic techniques. Significant carbon losses were observed in all materials with highest in grass (40% and 47% for mesophilic and thermophilic decomposition, respectively). For HW, grass and ONP, the carbon losses could be attributed primarily to cellulose and hemicellulose and some fraction of lignin. In SW, the carbon loss could be attributed to the uncharacterized carbon fractions (e.g. extractives etc.). 2D nuclear magnetic resonance (NMR) spectra showed slight reduction of β-O-4 linkage in HW, grass and ONP. Klason and acid soluble lignin as well as CuO lignin data indicate no substantial de-polymerization suggesting that reactivity of lignin were limited to side chain with no destruction of the aromatic structure. © Copyright 2014 Florentino B. De la Cruz All Rights Reserved Fate and Reactivity of Lignin in Municipal Solid Waste (MSW) Landfill by Florentino B. De la Cruz A dissertation submitted to the Graduate Faculty of North Carolina State University in partial fulfillment of the requirements for the Degree of Doctor of Philosophy Civil Engineering Raleigh, North Carolina 2014 APPROVED BY: Morton A. Barlaz Detlef Knappe Chair of Advisory Committee Advisory Committee Christopher Osburn Dimitris Agyropoulos Advisory Committee Advisory Committee DEDICATION Para sa aking mga magulang Eriberto De la Cruz at Gaudencia Banaag-De la Cruz salamat sa pamanang edukasyon sa kabila ng kahirapan. (To my parents Eriberto De la Cruz and Gaudencia Banaag-De la Cruz thank you for the gift of education.) ii BIOGRAPHY Florentino De la Cruz received his Bachelor of Science degree in Chemical Engineering from the University of the Philippines Los Baños in 2001. In 2002, he worked as a laboratory analyst at United Laboratories Inc. In 2003, he was employed as an instructor at Department of Engineering Science at the University of the Philippines Los Baños where he taught courses such as advance engineering graphics, differential equations and fluid mechanics. He received his Master of Science degree in Chemical Engineering with minor in Environmental Science from the same university in 2007. In 2008, he joined Dr. Morton Barlaz at North Carolina State University and started working on his doctoral degree in Environmental Engineering. As a PhD student, he has been involved in several solid waste projects including the development of a model to estimate carbon footprint of a landfill, hydrogen sulfide attenuation and municipal solid waste decomposition. His dissertation research is about the chemical characterization and understanding of the chemical changes during anaerobic decomposition of lignocellulose in anaerobic environment such as landfills. iii ACKNOWLEDGEMENTS I am glad to admit that I was quite inadequate in so many aspects when I started this work because in that way I was compelled to reach out for help and in the process meet quite a number of wonderful people sharing not only lessons in professional field but more importantly on how to become a better person. I apologize if for whatever reason, I missed to mention anyone to whom I am indebted. To my adviser Dr. Barlaz for the guidance and patience. It has been a good learning years being under your supervision. I have learned about so many things with every project that I handled. Thank you for everything. To my committee (Drs. Knappe, Osburn and Agyropoulos) for your suggestions and for your considerations. Discussions with you have been important input for the improvement of this work. To my family in the Philippines who have been my source of strength when I felt like giving up. To Gigi for the support and inspiration. To my UPLB ES Department family, thank you for believing in me. I am hoping to re- join the department soon. To David Black for assistance in the lab and for helping students beyond what is called for by your job. iv To Yinglong Guan and Michael Mondou for the conscientious work on CuO analysis. Without your help I would not have been able to finish this work. To Dr. Gracz of the Department of Structural Biochemistry thank you for trusting in me, for your support and for the inspiration to finish this work. I have learned so much about NMR spectroscopy in just a short time. To Dr. Pezslen of Department of Forest Biomaterials for the help in wood identification and for sharing your wood collection for this work. I could finally answer yes whenever you ask me if I graduated already. To Drs. Dittmar and Niggeman of Max Planck Institute in Germany thank you for our exchanges of ideas and for letting me visit your lab to learn more about CuO analysis. To Joe Cox College Forest Manager NCSU Department of Forestry and Environmental Resources for facilitating in sample collection at Schenk Forest. To Dr. Richard Braham of Department of Forestry as well as Dr. Alexander Krings and Dr. Mark Weathington (life is too short for boring plants) of JC Raulston Arboretum for the help in the collection and identification of different plant tissues To Jason Patskotsky for help with Matlab programming. To my Filipino friends at NC State Jason So, Remil, Tony, Jules Cacho and Dr. De los Reyes for the company. You guys made living away from family more bearable. To Saquing Family, thank you for making me feel like a part of your family. Hope to get together with you soon. v To Drs. Osborne and Maity for the advice on statistics. To NC State Turf People Bill Beardall and April Bauder for providing grass samples. The golf cart ride was fun! To Dr. Yelle for generously sharing knowledge about NMR spectroscopy especially HSQC contour assignments and for letting me visit your lab for research collaboration. To the Solid Waste Research Group (aka Hot room residents), Jenny Padgett (my first research lab mate), Xiaoming, Jim, Johnsie, Milla, Joe, Wenji and Mei for the friendship. To the undergrads who have helped me in different projects: Australia (Josh, John); Plastics Biodegradation (Mark); Wood decomposition (Niel); Sulfide (Analee, Caroline, Mike, Matt, Chris, Trevon, Rachel, Mark). To my officemates at Mann 223 and to Environmental lab people thanks for the conversations whenever we had time. To Birgit Anderson from Textiles department for help within FT-IR spectroscopy. To Dr. Ralph for answering my questions and his inputs on NMR spectroscopy and plant cell wall dissolution. To my roommates Brian and Thomas thank you for the listening to my stories. I know you didn’t really understand some of the technical stuff I was telling but still you listen. To Raleigh Catholic community and Sacred Heart Cathedral Saturday Folk Choir where I met wonderful people and at the same time learn more about music.
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