Production of value added chemicals from rice straw

VIETNAM NATIONAL UNIVERSITY HO CHI MINH CITY HO CHI MINH CITY UNIVERSITY OF TECHNOLOGY * - LE MINH TAN PRODUCTION OF VALUE-ADDED CHEMICALS FROM RICE STRAW Major: Chemical engineering Code: 8520301 MASTER THESIS Ho Chi Minh, July - 2021 THIS RESEARCH WAS CONDUCTED AT HO CHI MINH CITY UNIVERSITY OF TECHNOLOGY VNU-HCM Supervisor 1: Dr Tran Tan Viet Supervisor 2: Assoc Prof Dr Le Thi Kim Phung Reviewer 1: Dr Tran Phuoc Nhat Uyen Reviewer 2: Dr Pham Thi Hong Phuong The master thesis was defended at Ho Chi Minh city University of Technology, VNU-HCM, July 9th, 2021 (Online) The members of Assessment Committee including: Assoc Prof Dr Nguyen Quang Long - Chairman Dr Tran Phuoc Nhat Uyen - Reviewer Dr Pham Thi Hong Phuong - Reviewer Dr Nguyen Thi Le Lien - Committee Dr Dang Bao Trung - Secretary Confirmation of the Assessment Committee Chairman and the Head of Faculty after the thesis has been corrected (if any) Assessment Committee Chairman Assoc Prof Dr Nguyen Quang Long Dean of Chemical Engineering Faculty Prof Dr Phan Thanh Son Nam VIETNAM NATIONAL UNIVERSITY - HCM SOCIALIST REPUBLIC OF VIETNAM HO CHI MINH CITY UNIVERSITY OF Independence - Freedom - Happiness TECHNOLOGY MASTER THESIS MISSIONS Full Name: LE MINH TAN Student Date of Birth: 23/12/2997 Place of Birth: Tien Giang Major: Chemical engineering Code: 8520301 I THESIS TITLE: PRODUCTION OF VALUE-ADDED CHEMICALS FROM RICE STRAW MISSIONS AND CONTENTS: - Production of lignin from rice straw through pre-treatment method - Integration of delignification process, and bioethanol production for creating zerowaste biorefinery - Conversion obtained lignin into bio-oil - Evaluation of biorefinery approach, and creating the life cycle thinking of rice straw II DATE OF ASSIGNMENT: 22/02/2021 III DATE OF COMPLETION: 05/12/2021 IV SUPERVISORS: Dr Tran Tan Viet Assoc Prof Dr Le Thi Kim Phung Ho Chi Minh city, SUPERVISORS Dr Tran Tan Viet /08/2021 HEAD OF DEPARTMENT Assoc Prof Dr Le Thi Kim Phung Assoc Prof Dr Le Thi Kim Phung DEAN OF CHEMICAL ENGINEERING FACULTY Prof Dr Phan Thanh Son Nam ACKNOWLEDGEMENTS There are no proper words to convey my deep gratitude and respect for my thesis and research advisors, Dr Tran Tan Viet and Assoc Prof Le Thi Kim Phung They have inspired me to become an independent researcher and helped me realize the power of critical reasoning They also demonstrated what a brilliant and hardworking scientist can accomplish My sincere thanks must also go to my brilliants friends in, who is always besides me from joyful moments to hard time, cheered me on, and celebrated each accomplishment I will also never forget the sleepless nights in many coffee shops and the buffet parties Additionally, I really appreciate with help of Dr Tran Phuoc Nhat Uyen who I am most grateful to the collaborators for giving me many memories in at RPTC There is no way to express how much it meant to me to have been a member of RPTC Last but not the least, I would like to express my gratitude to my family for their unfailing emotional support, unconditional trust, timely encouragement, and endless patience I acknowledge the support of time and facilities from Ho Chi Minh City University of Technology (HCMUT), VNU-HCM for this study Ho Chi Minh city, July-2021 Le Minh Tan ABSTRACT Rice straw, the main agricultural wastes from rice production, has great potential to be converted into value-added raw materials In this study, the benefits of using rice straw in reducing the global dependency on fossil fuels and produce green chemicals were demonstrated by recovery process of high value material and integration of the process with bioethanol production for zero-waste biorefinery First, the study developed a method to reduce the silica content in lignin from rice straw more effectively and selectively The method is established by monitoring the precipitation behavior as well as the chemical structure of precipitate by singlestage acidification at different pH values of black liquor collected from the alkaline treatment of rice straw The simple two-step acidification of the black liquor at pilot-scale by sulfuric acid 20 w/v% is applied to recover lignin at pH and silica at pH and gives a percentage of silica removal as high as 94.38% Next, a pilot-scale biorefinery, whose bioethanol production from rice straw was an integrated recovery system for lignin, silica, and nutrient recovery was continuously developed The recovery yield of silica and lignin from the black liquor of alkaline pretreatment was up to 96%, and the lignin purity reached 79% without the existence of carbohydrate fiber After the recovery, the final liquid waste mainly contained inorganic matters and has a potential to be reused in the acidification step The distillation residue was a nitrogen source for simultaneous saccharification and fermentation equivalent to corn steep liquor with the final ethanol concentration of 1.6 wt.% in 160 hours The material flow indicated that more valued products produced by the simple method increase the profits of this process Also, the energy efficiency of the process was 0.53 that demonstrated the process's economy and sustainability Additionally, silica derived rice husk was used to synthesize ZSM-5 and Ni/ZSM-5 to catalyze for hydro processing of rice straw lignin for the first time The results show the high yield of bio-oil of 24.4 wt% and phenolic content of 41.2 wt.% when using Ni/ZSM-5 Finally, the full life cycle thinking of rice residues was also argued in this study m t ph ph m ch nh qu cao trình , thu silica lignin eo, , lignin s d ng Ngoài ra, ZSM-5 Ni/ZSM-5 làm xúc tác cho trình c lignin thành biocrude phenolic 41.2% k xúc tác Ni/ZSM- DECLERATION I hereby declare that the thesis has been composed by myself and that the work has not be submitted for any other degree or professional qualification I confirm that the work submitted is my own, except where work which has formed part of jointly-authored publications has been included My contribution and those of the other authors to this work have been explicitly indicated below I confirm that appropriate credit has been given within this thesis where reference has been made to the work of others A part of the work presented in this thesis was my publication, which was previously published in Scientific Report as The novel method to reduce the silica content in lignin recovered from black liquor originating from rice straw Clean Technologies and Environmental policy as Sustainable bioethanol and value-added chemicals production from paddy residues at pilot scale The Author Le Minh Tan July 2021 i CONTENTS CONTENTS i LIST OF TABLES v LIST OF ABBREVIATIONS vi CHAPTER PREFACE 1.1 Study Background 1.2 Research aims and Objectives 1.3 Outline of thesis CHAPTER LITERATURE REVIEW 2.1 Rice straw a potential lignocellulose biomass overview 2.1.1 Lignocellulosic biomass 2.1.2 Rice straw 2.2 Rice straw- based biorefinery 2.3 Production of rice straw lignin 2.4 Conversion of straw lignin into bio-oil 11 2.5 Circular bioeconomy 12 CHAPTER MATERIALS AND METHODS 14 3.1 Chemicals and Materials 14 3.2 Experiments 14 3.2.1 Rice straw pretreatment 14 3.2.2 Insight the precipitation behavior of black liquor in different pH values 14 3.2.3 Lignin recovery by 2-step acidification 15 3.2.4 Synthesis Ni/ZSM-5 from rice husk silica 15 3.2.5 Conversion of rice straw lignin into bio-oil 16 ii 3.3 Characterization and analysis 17 3.3.1 Lignin characterization 17 3.3.2 Catalyst characterization 17 3.3.3 Bio-oil characterization 18 CHAPTER RESULTS AND DISCUSSIONS 20 4.1 Lignin recovery with lower silica effects 20 4.1.1 Rice straw composition 20 4.1.2 Insight the precipitation behavior of black liquor in different pH values 20 4.1.3 Two-step acidification method for lignin and silica recovery 27 4.2 Hydroprocessing of lignin 31 4.2.1 Catalyst characterization 31 4.2.2 Catalytic hydroprocessing of lignin 35 4.2.3 Products analysis 36 4.3 Scale-up into pilot scale and integrated with bioethanol production process 40 4.3.1 Production of lignin in pilot scale 40 4.3.2 Integrated with the bioethanol production process 44 4.4 Circular bioeconomy analysis 47 CHAPER CONCLUSION AND FUTURE WORKS 51 LIST OF PUBLICATION 53 REFERENCES 54 SHORT CURRICULUM VITAE 65 iii LIST OF FIGURES Figure 1.1 The scientific idea of this study Figure 2.1 The structure of lignocellulose biomass Figure 2.2 Three type of lignin monomers: (A) p-coumaryl alcohol (hydroxyphenyl unit), (B) coniferyl alcohol (guaiacyl units), and (C) sinapyl alcohol (syringyl unit) Figure 2.3 Burning rice straw in field (a) and Using rice straw for animal feeds (b) Figure 2.4 The biorefinery in Vietnam Figure 3.1 Schematic representation of the process of recovery of lignin and silica from rice straw 15 Figure 4.1 Mass of total precipitate, ash, and non-ash in the black liquors 21 Figure 4.2 The color variation of the precipitate (a) and the filtrates of black liquors (b) at different pH values from to 10 22 Figure 4.3 FTIR and XRD spectrums of the precipitate from pH 10 to pH (a,c) and from pH to pH (b,d) 24 Figure 4.4 TG analysis of the precipitates from pH 10 to (a) and from pH to (b) 26 Figure 4.5 The recovery yield of lignin and silica, the ash content of lignin in difference processes 28 Figure 4.6 FTIR (a) and XRD (b) spectrums of lignin in a two-steps process 29 Figure 4.7 The recovery yield, the purity, and the silica content of lignin in several concentrations of NaOH 30 Figure 4.8 The XRD diffractograms of ZSM-5 and Ni/ZSM-5 (a), SEM micrographs of ZSM-5 (b) and Ni/ZSM-5 (d) and the TPD-Br of ZSM-5 and Ni/ZSM-5 (c) 32 Figure The BET isotherms of ZSM-5 and Ni/ZSM-5 34 51 CHAPER CONCLUSION AND FUTURE WORK Conclusion: In this study, the biorefinery based on residues and waste from the rice production chain (straw) represents an opportunity both to minimize waste production and to add more value in to those components which are associated with thea disposal cost The following findings were obtained as a result of the research: Firstly, the effects of pH value on the behavior of the precipitates of lignin and silica from the black liquor of rice straw have been comprehensively investigated by step-by-step acidification with dilute H2SO4 The color of the precipitate changes from golden brown to dark brown with decreasing pH value, whereas the opposite trend is true for the filtrate The pH value of is demonstrated to recover lignin most effectively based on chemical structure analysis, while a pH range of 10-8 was demonstrated to remove silica from the black liquor A two-step acidification process was developed with prior acidification of diluted sulfuric acid to pH and removal of silica, followed by acidification to pH for optimal lignin recovery These findings will be useful in mass production to identify lignin recovery during the acidification of black liquor Moreover, in the view of industrialization, by utilizing low concentration basic chemicals such as NaOH 1% and H2SO4 20%, this method not only produces value-add products but also saves energy and lowers waste in the environment because of its simplicity and efficiency By using diluted sodium hydroxide at a low concentration of 1w/v%, the precipitate obtained at pH has the highest lignin purity of 65.74%, a recovery yield of 66.75%, and a silica reduction of 94.38% Also, in this study, the biorefinery process with the zero-waste discharge concept was established thanks to the reuse and recovery of the waste stream with more valuable products produced The new system's energy consumption is more effective than the previous one, with an energy efficiency of 0.529 Lignin and silica were successfully recovered from black liquor generated from the bioethanol plant on a pilot scale with a high recovery yield Reusing the distillation residue as a Nitrogen source for the SSF step could reduce the purchase cost for CSL This biorefinery process, which is more sustainable than bioenergy production alone, promises a potential solution to sustainable development goals by providing higher-value creation 52 Finally, the rice residue's potential was demonstrated by the close life cycle, built by the chain of a simple method to improve its value The cycle could be an excellent way to lay the groundwork for developing a biorefinery model that adds more value to the rice production chain while adhering to circular bioeconomic principles Besides, the depolymerization of rice straw lignin was performed efficiently by Ni/ZSM-5 and ZSM-5 catalysts derived from rice husk The highest yield of liquid product (24.42 wt.%) and phenolic compounds (41.2 wt.%) was obtained from the Ni/ZSM-5 catalyzed reaction Future works: Besides the achievements, there is some work that needs to be conducted to make the research better These following works were suggested by the author based on circular bioeconomy principles and biorefinery concepts: - Statistics from the economic database for biorefineries in Vietnam potential biomass, price of bio-fuel in the Vietnam market, cost of building biorefinery, and so on - Analyzing the new process using Life Cycle assessment tools, Techno-economy, Socio-economy for sustainability - Investigating the use of biocrude in the production of biofuels, bio-based chemicals, etc - Studying on utilizing bio-char for producing bio-materials 53 LIST OF PUBLICATION T M Le et al., Sustainable bioethanol and value-added chemicals production from paddy residues at pilot scale Clean Technologies and Environmental policy, vol 20, 2021 N H Do et al., Scientific Reports, vol 10, pp 21-26, 2020 N H Do et al., Lignin and sodium lignosulfonate production from the black liquor generated during the production of bioethanol from rice straw Journal of Science and Technology, vol 58, pp 63-72, 2021 Vietnam 54 REFERENCES [1] M D Ferro et al Biochemical Engineering Journal, vol 104 pp 98 105, 2015 [2] T L C Oldoni et al extraction process of bioactive compounds from propolis 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Date of Birth: 23/12/2997 Place of Birth: Tien Giang Major: Chemical engineering Code: 8520301 I THESIS TITLE: PRODUCTION OF VALUE- ADDED CHEMICALS FROM RICE STRAW MISSIONS AND CONTENTS: - Production. .. in lignin recovered from black liquor originating from rice straw Clean Technologies and Environmental policy as Sustainable bioethanol and value- added chemicals production from paddy residues... Figure 4.18 The mass estimation of bioconversion of rice straw and rice husk in biorefinery concept 50 v LIST OF TABLES Table 4.1 The composition of rice straw and black liquor