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Understanding Cellulose Primary and Secondary UNDERSTANDING CELLULOSE PRIMARY AND SECONDARY PYROLYSIS REACTIONS TO ENHANCE THE PRODUCTION OF ANHYDROSACCHARIDES AND TO BETTER PREDICT THE COMPOSITION OF CARBONACEOUS RESIDUES By ZHOUHONG WANG A dissertation submitted in partial fulfillment of the requirements for the degree of DOCTOR OF PHILOSOPHY WASHINGTON STATE UNIVERSITY Department of Biological Systems Engineering DECEMBER 2013 To the Faculty of Washington State University: The members of the Committee appointed to examine the dissertation of ZHOUHONG WANG find it satisfactory and recommend that it be accepted. ___________________________________ Manuel Garcia-Pérez, Ph.D., Chair ___________________________________ Armando G. McDonald, Ph.D. ___________________________________ Su Ha, Ph.D. ___________________________________ Shyam S. Sablani, Ph.D. ii ACKNOWLEDGMENT I would like to thank Dr. Manuel Garcia-Perez for his support and advice during my PhD studies. It’s my great honor to learn from his passion on research and his oversight of my research. I would like to thank my committee members: Dr. Armando McDonald, Dr. Su Ha, and Dr. Shyam Sablani for their kind guidance and continued participation. I would like to thank Prof. Sascha Kersten for the support during my visit to his group (Sustainable Process Technology (original Thermal Chemical Conversion of Biomass), University of Twente, the Netherlands). Thanks to all the members in SPT group (Prof Wim van Swaaij, Prof. Jean-Paul Lange, Prof. van den Berg, Dr. Wim Brilman, Dr. Louis van der Ham, Dr. Guus van Rossum, Dr. BoeloSchuur, Dr. Roel Westerhof, Dr. Michal Gramblicka, Johan Agterhorst, Karst van Bree, Erna Fränzel-Luiten, Benno Knaken, Yvonne Bruggert-ter Huurne, Maria Castellvi Barnes, Laura Garcia Alba, Stijn Oudenhoven, Rens Contact, Ying Du, Xiaohua Li, Jeroen de Graaf, Joram Boegborn, Tim Hilbert, Michiel van Kuppevelt) for the help and joy they kindly offered. Special thanks to Dr. Roel Westerhof for all his help and recommendations when writing my papers. Also I would like to thank all the staff members in our department (Wayne DeWitt, Vincent Himsl, Joan Hagedorn, Jonathan Lomber, John Anderson, Dorota Wilk, Pat Huggins and Pat iii King), who helped me in the lab with the instruments, dealing with financial problems, and on the administrative work. Really thank you for all the support and help you offered. My colleagues (Shuai Zhou, Shi-Shen Liaw, Brennan Pecha, Matt Smith, Jieni Lian, Robert Johnson, Filip Stankovikj, Jesus A Garcia, Raul Pelaez, Waled Suliman), thank you for all those nice and enlightening discussions during my whole time at Washington State University. And also thank you for those great hang outs. I really enjoyed my time here in both studying and living. iv UNDERSTANDING CELLULOSE PRIMARY AND SECONDARY PYROLYSIS REACTIONS TO ENHANCE THE PRODUCTION OF ANHYDROSACCHARIDES AND TO BETTER PREDICT THE COMPOSITION OF CARBONACEOUS RESIDUES Abstract by Zhouhong Wang, Ph.D. Washington State University December 2013 Chair: Manuel Garcia-Perez Pyrolysis is a promising method to convert biomass into an oil that can be refined into valuable fuels and chemicals as well as a carbonaceous residue that can be converted into adsorbents. In pyrolysis, cellulose, the most abundant biomass constituent, is thermally converted into mono- and oligo-anhydrosugars (chiefly levoglucosan and cellobiosan) in high yields with small quantities of a carbonaceous “bio-char” residue. However, the reaction mechanisms for cellulose pyrolysis have not been well investigated. The major goal of this dissertation is to advance our knowledge on the pyrolysis mechanisms responsible for the formation of anhydrosugars and carbonaceous residues under slow and fast pyrolysis. Our hypothesis is that under fast heating rate conditions, cellulose forms a very reactive liquid intermediate of cellulose primary products (levoglucosan, cellobiosan) which, if v not evaporated fast enough, will undergo cross-linking reactions. Cross-linked product formation is a critical step for the formation of carbonaceous residues under slow heating rate conditions. It was found that cellulose crystallinity can affect the formation rate of this liquid intermediate, which is promoted by amorphous state. Our research shows that this liquid state is a temperature controlled step that enhances dehydration reactions and cross-linking reactions if persistent. We also determined that secondary reactions in the liquid phase derive not from levoglucosan remaining in the liquid phase, but from oligo-anhydrosugars like cellobiosan. Extended studies found sulfuric acid inducing dehydration and cross-linking reactions during pyrolysis of cellulose and levoglucosan. In pyrolysis of cellobiosan, sulfuric acid increased the yield of levoglucosan. The concentration of sulfuric acid at which the yield of levoglucosan from the pyrolysis of Douglas fir wood is maximized near the yield was found from cellulose. The changes occurred during slow heating of cellulose were studied using 13C-NMR, FTIR, IEC and SEM. A new reaction mechanism that includes the formation of cross-linked sugars was developed to explain the evolution of carbonaceous residues from cellulose pyrolysis at slow heating rates. The results in this dissertation provide fundamental insights into cellulose thermal reactions for developing new strategies to enhance yield of anhydrosugars or valuable chemicals and to better predict the composition of carbonaceous residues formed. vi Table of Contents ACKNOWLEDGMENT................................................................................................................ iii Abstract ............................................................................................................................................v Table of Contents .......................................................................................................................... vii List of Tables ...................................................................................................................................x List of Figures ................................................................................................................................ xi Chapter 1 Introduction .....................................................................................................................1 1.1 Multiscale Structure of Lignocellulosic Materials ................................................................ 3 1.2 Cellulose ............................................................................................................................... 4 1.3 Cellulose Characterization .................................................................................................... 5 1.4 Cellulose Thermochemical Reactions .................................................................................. 8 1.5 Conclusions of literature review ......................................................................................... 32 1.6 Dissertation objective ......................................................................................................... 33 1.7 Methodology ....................................................................................................................... 34 1.8 Publications ......................................................................................................................... 36 Reference .................................................................................................................................. 40 Chapter 2 Effect of Cellulose Crystallinity on the Formation of a Liquid Intermediate and on Product Distribution during Pyrolysis ......................................................................................49 2.1 Introduction ......................................................................................................................... 51 2.2 Materials and Methods ........................................................................................................ 53 2.3 Results and Discussions ...................................................................................................... 55 2.4 Conclusions ......................................................................................................................... 73 vii Acknowledgements ................................................................................................................... 74 Reference .................................................................................................................................. 75 Chapter 3 Effect of Pyrolysis Temperature on the Formation of Anhydrosugars during the Fast Pyrolysis of Cellulose in a Wire Mesh Reactor at Atmospheric Pressure .............................80 3.1 Introduction ......................................................................................................................... 83 3.2 Materials and Methods ........................................................................................................ 86 3.3 Results and Discussions ...................................................................................................... 92 3.4 Conclusions ....................................................................................................................... 106 Acknowledgement .................................................................................................................. 107 Reference ...............................................................................................................................
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