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Development of a Propylene Glycol-Based Organosolv Process for Biomass Fractionation Chemical Engineering

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Development of a Propylene Glycol-Based Organosolv Process for Biomass Fractionation Chemical Engineering Development of a propylene glycol-based organosolv process for biomass fractionation Bruno Filipe Chanca Sampaio Thesis to obtain the Master of Science Degree in Chemical Engineering Supervisors: Dr. Luís C. Duarte Prof. Maria Joana Castelo-Branco de Assis Teixeira Neiva Correia Examination Committee Chairperson: Prof. Maria Teresa Nogueira Leal da Silva Duarte Members of the committee: Dr. Maria Margarida Pires dos Santos Mateus Dr. Luís C. Duarte October 2019 Declaration I declare that this document is an original work of my own authorship and that it fulfills all the require- ments of the Code of Conduct and Good Practices of the Universidade de Lisboa. iii Acknowledgments To my parents that provided me with everything I am today. To Dr. Luís Duarte, for being my mentor, pushing me to do better and treating my career as if it was his. To Professor Joana Neiva Correia for all the availability, knowledge and final revisions. To Dr. Américo Martins for kindly introducing me to the ASE system as well as for explaining its opera- tion. To Dr. Cristina Oliveira for allowing me to use the ASE equipment and providing every necessary dili- gence. To Dr. Florbela, Dr. Luísa, Dr. Roseiro, Patrícia, for every contribution to this work. To Céu and Belina, for all their knowledge and technical support, particularly with HPLC and the NREL protocols. To Vanmira for struggling with me, being my support and coffee buddy during this journey. To Diogo, for always being the funniest person in the room. To Luís, Cláudia, Pedro, Vicente, Yuliya, for all the help and all the laughter during lunch breaks. To all my friends and colleagues at LNEG, for always being ready to help. To all my friends at IST, who made the past five years an awesome adventure. To everybody who made this work possible. To all, THANK YOU, very much! v Resumo A etapa de pré-tratamento representa uma fração substancial dos custos operatórios do pro- cessamento da biomassa, representando um enorme impacto no desempenho económico e ambiental das biorefinarias. Assim, o desenvolvimento das estratégias de pré-tratamento é visto como uma peça- chave no impulsionamento da competitividade económica da conversão da biomassa. Nomeadamente, o propilenoglicol é considerado um solvente renovável, seguro, não-inflamável e não-tóxico, preferível a outros solventes mais tradicionais, como o etanol e a acetona. Neste trabalho, um processo organosolv com propilenoglicol foi avaliado para a desconstrução de resíduos de eucalipto e palha de trigo. Foi estudado o efeito das condições de pré-tratamento na solubilização dos diferentes componentes da biomassa e na sua digestibilidade enzimática, bem como o efeito de catalisadores e da transição para operação em contínuo. No tratamento com uma solução aquosa com 75% de propileno glicol e 0,5% de ácido sulfúrico, a 160ºC durante 15 minutos, obteve-se solubilizações de xilano e lenhina acima de 80%, em simultâneo com recuperações de celulose de 90%, revelando uma digestibilidade enzimática de 89%. A operação em contínuo resultou numa maior solubilização de xilano e lenhina, acompanhada por uma menor for- mação de produtos de degradação. Além disso, permitiu ainda a recuperação de 60 a 80% da lenhina inicial, na forma sólida, simplificando os processos de separação e recuperação de solvente a jusante. Estes resultados revelam o potencial do processo proposto para competir com outros proces- sos organosolv, dado que apresenta um desempenho semelhante em condições operatórias mais su- aves, com o respetivo ganho em custos de capital e operatórios. Palavras-chave: bioeconomia circular; biomassa lenhocelulósica; biorefinaria; pré-tratamento orga- nosolv; propilenoglicol; solvente não-volátil. vii Abstract Biomass pretreatment represents a substantial fraction of biomass processing costs and has great impact on economic and environmental performance of the biorefinery. Hence, improvements in pre-treatment strategies are widely recognized as a key way to improve the economic competitiveness of biomass conversion. Particularly, propylene glycol (PG) is a green, high-boiling, safe, non-toxic and non-flammable solvent, less hazardous than most commonly used solvents in organosolv processes, such as ethanol and acetone. In this work, a PG-based organosolv pretreatment was evaluated for the deconstruction of eu- calyptus residues and wheat straw, as model feedstocks. Pretreatment conditions and their effect on the solubilization of lignocellulosic components and enzymatic digestibility of pretreated solids were dis- cussed, as well as the effect of catalyst use and transition to flow-through operation. Xylan and lignin solubilization values above 80% were obtained for pretreatment at 160ºC for only 15 minutes with 75%PG and 0.5% of sulfuric acid. For those conditions, cellulose recovery reached 90% in the pretreated solids, resulting in 89% enzymatic digestibility. Flow-through operation mode en- abled the solid recovery of 60-80% of total lignin in feedstocks, simplifying downstream process design. Furthermore, flow-through regime allowed an increased lignin and xylan solubilization, as well as re- duced formation of degradation products, when compared to batch operation. These results suggest the ability of the proposed process to compete with other organosolv methods, as it originates similar yields at much milder operation conditions, with the respective gains in capital and operational costs. Keywords: circular bioeconomy; lignocellulosic biomass; biorefinery; organosolv pretreatment; propyl- ene glycol; high-boiling solvent. ix Table of contents Declaration .............................................................................................................................................. iii Acknowledgments ....................................................................................................................................v Resumo .................................................................................................................................................. vii Abstract.................................................................................................................................................... ix Table of contents ..................................................................................................................................... xi List of tables ........................................................................................................................................... xv List of figures ........................................................................................................................................ xvii Notation ................................................................................................................................................. xxi Framework ........................................................................................................................................... xxiii Funding ............................................................................................................................................ xxiii Thesis structure ............................................................................................................................... xxiii Publications by chapter ................................................................................................................... xxiv 1. General introduction ........................................................................................................................ 1 1.1. Lignocellulosic Feedstocks ........................................................................................................... 2 1.2. Pretreatment Review .................................................................................................................... 4 1.3. The organosolv processes ......................................................................................................... 11 1.3.1. Solvent options .............................................................................................................. 12 1.3.1.1. Alcohols ..................................................................................................................... 12 1.3.1.2. Organic acids ............................................................................................................. 14 1.3.1.3. Ketones ...................................................................................................................... 14 1.3.1.4. Amines ....................................................................................................................... 15 1.3.1.5. Dioxane ...................................................................................................................... 15 1.3.1.6. -valerolactone ........................................................................................................... 15 1.3.1.7. Alkylene carbonates .................................................................................................. 16 1.3.1.8. Polyhydric alcohols .................................................................................................... 19 1.3.2. Mechanism of organosolv pretreatment ........................................................................ 22 1.3.3. Towards commercialization ........................................................................................... 23 1.4. Objectives ..................................................................................................................................
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