(Luận văn thạc sĩ) chế tạo hệ phân tán graphene oxide copolymer nanocomposite ổn định định hướng ứng dụng trong tăng cường thu hồi dầu tại các vỉa xa bờ nhiệt độ cao

HOANG ANH QUAN MINISTRY OF EDUCATION AND TRAINING VIETNAM ACADEMY OF SCIENCE AND TECHNOLOGY GRADUATE UNIVERSITY OF SCIENCE AND TECHNOLOGY ORGANIC CHEMISTRY Hoang Anh Quan DESIGN OF STABLE GRAPHENE OXIDE-COPOLYMER NANOCOMPOSITE DISPERSION ORIENTATED FOR EOR APPLICATION IN HIGH-TEMPERATURE OFFSHORE RESERVOIRS Major : Organic Chemistry Code: 8440114 MASTER THESIS ORGANIC CHEMISTRY 2021 Ho Chi Minh City - 2021 Luan van MINISTRY OF EDUCATION VIETNAM ACADEMY OF AND TRAINING SCIENCE AND TECHNOLOGY GRADUATE UNIVERSITY OF SCIENCE AND TECHNOLOGY Hoang Anh Quan DESIGN OF STABLE GRAPHENE OXIDE-COPOLYMER NANOCOMPOSITE DISPERSION ORIENTATED FOR EOR APPLICATION IN HIGH-TEMPERATURE OFFSHORE RESERVOIRS Major: Code: Organic Chemistry 8440114 MASTER THESIS SCIENTIFIC SUPERVISOR: Dr Luu Anh Tuyen Assoc Prof Dr Nguyen Phuong Tung Ho Chi Minh City - 2021 Luan van ASSURANCE FOR MASTER THESIS I assure you that the data and research results in this master thesis are my research work based on documents and data that I have researched myself Therefore, the research results ensure the most honesty and objective At the same time, this result has never appeared in any other study Any help in this thesis was thanked and reference information such as method, data, figures, and pictures was cited clearly The data and results stated in the thesis are honest, if wrong, I will take full responsibility Ho Chi Minh city, October 31st, 2021 Learner Hoang Anh Quan Luan van ACKNOWLEDGMENT Throughout the writing of this dissertation, I have received a great deal of support and assistance I would first like to thank my scientific supervisors, Assoc Prof Dr Nguyen Phuong Tung and Dr Luu Anh Tuyen, whose expertise were invaluable in formulating the research questions and methodology Your insightful feedback pushed me to sharpen my thinking and brought my work to a higher level I would like to acknowledge my research group from Materials for enhanced oil recovery and energy conversion Lab - Institute of Applied Materials Science, who were always interested and enthusiastically supported me during the study period and completed this thesis experiment I would also like to thank lecturers from Graduate University of Science and Technology, for their valuable guidance throughout my studies You provided me with the knowledge and tools that I needed to choose the right direction and complete my dissertation In addition, I would like to thank my parents for their wise counsel and sympathetic ear You are always there for me Finally, I could not have completed this dissertation without the support of my friends, who provided stimulating discussions and happy distractions to rest my mind outside of my research Luan van ABSTRACT Thermostable and highly water-soluble polymers are essential for polymer flooding — one of the most effective methods used in the enhanced oil recovery (EOR) in hightemperature (HT) offshore reservoirs In this research, the copolymerization reaction of acrylamide (AM) and N-vinylpyrrolidone (NVP) monomers were performed via a freeradical mechanism induced by gamma-rays (γ-rays) irradiation The impact of input data (the ratio and the concentration of the monomer to product-solution viscosity) was scanned in detail and used to optimize the copolymerization conditions The optimal viscosity values of the polymer concentration were 0.5 wt.% Therefore, the optimal conditions for copolymerization were obtained at 1.7 for AM/NVP monomer ratios and 23.2 wt.% for monomers concentration The copolymerization induced by γ-rays irradiation in optimized conditions was then carried out, and the obtained viscosity of 0.5 wt.% of produced copolymers solutions was 5.02 cP These results were in good agreement with the calculated values The obtained copolymers were then covalently coupled with graphene oxide (GO) synthesized from natural graphite using the modified Hummer’s method The product nanocomposites, called GO–P(AM-NVP), were characterized by Fourier transform infrared spectroscopy, Raman spectroscopy, scanning electron microscopy, and gel permeation chromatography The thermal and chemical stabilities of brine-dispersed P(AM-NVP) copolymers annealed at 123 °C (the WT Miocene reservoir temperature) and GO–P(AM-NVP) nanocomposite dispersion annealed at 135 °C (the WT Oligocene reservoir temperature) for 31 days were observed via visual inspection and viscosity testing Results indicated that the dispersions of P(AM-NVP) copolymers and P(AM-NVP) copolymers conjugated on GO nanosheets have excellent thermal and chemical stabilities and hence became a promising agent for EOR in HT offshore reservoirs Luan van GRAPHICAL ABSTRACT Luan van Hoang Anh Quan – Master thesis Contents CONTENTS CONTENTS i LIST OF FIGURES iv LIST OF TABLES vii LIST OF ABBREVIATION viii INTRODUCTION Chapter 1: Literature Review 1.1 Enhanced oil recovery (EOR) 1.1.1 Introduction to Enhanced oil recovery 1.1.2 Mechanism of enhanced oil recovery 1.1.3 Enhanced oil recovery methods 1.2 Polymers 1.2.1 Introduction 1.2.2 Polymers in EOR 1.2.2.1 Biologically produced polymer (biopolymer) 1.2.2.1 Synthetic polymer 10 1.2.3 Synthesis of EOR polymers 11 1.2.5 Mechanism of polymer flooding in EOR process 14 1.2.5.1 Capillary Number (Nc ) 14 1.2.5.2 Polymer flooding in EOR 15 1.2.6 Gamma-rays irradiation-induced copolymerization 17 1.2.6.1 Free radical copolymerization 17 1.2.6.2 Radiation-initiated polymerization 18 1.3 GO–Polymer materials 19 1.3.1 P(N-vinylpyrrolidone–Acrylamide) copolymers 19 1.3.1.1 Acrylamide 19 i Luan van Hoang Anh Quan – Master thesis Contents 1.3.1.2 N-vinylpyrrolidone 20 1.3.2 Graphene oxide in EOR 21 1.3.3 The researches about GO–Polymers materials 22 1.3.4 The researches about GO–Popolymers materials in EOR 23 Chapter 2: Experimental 25 2.1 Chemical and materials 25 2.2 Equipment, instruments, software 27 2.3 Procedure 30 2.3.1 Graphene oxide (GO) preparation 30 2.3.2 Gamma-rays irradiation-induced copolymerization of AM and NVP monomers 31 2.3.3 Optimization 32 2.3.4 Synthesis of GO–P(AM-NVP) nanocomposite 33 2.4 Determination of the effect of the monomer composition and concentration on copolymers yield 34 2.5 Characterization measurements 35 2.6 Thermal and chemical stabilities of P(AM-NVP) and GO–P(AM-NVP) dispersions 35 Chapter 3: Results and Discussion 37 3.1 Effect of monomer composition and concentration on product yield, molecular weight, and product viscosity 37 3.2 Optimization 40 3.3 Characterization of P(AM-NVP) and GO–P(AM-NVP) 42 3.3.1 FTIR of GO, P(AM-NVP) and GO–P(AM-NVP) 42 3.3.2 Raman spectra of GO and GO–P(AM-NVP) 45 3.3.3 SEM analysis of P(AM-NVP) and GO–P(AM-NVP) 46 ii Luan van Hoang Anh Quan – Master thesis Contents 3.4 Evaluation of thermal and chemical stabilities of P(AM-NVP) copolymers and GO-P(AM-NVP) dispersions 48 3.4.1 Observing the appearance after being annealing 49 3.4.2 The viscosity of annealed samples 50 Chapter 4: Conclusions and Recommendations 52 4.1 Conclusions 52 4.2 Recommendations 53 LIST OF PUBLISHED PAPERS RELATED TO LEARNER 54 REFERENCES a APPENDIX e A.1 Pictures of the equipments and instruments e A.2 Pictures of the softwares .i iii Luan van Hoang Anh Quan – Master thesis List of Figures LIST OF FIGURES Figure 1.1 Oil recovery categories Figure 1.2 Target for different crude oil systems Figure 1.3 Effect of Nc on residual oil saturation Figure 1.4 Enhanced oil recovery methods Figure 1.5 Suitable monomers for free radical polymerization 12 Figure 1.6 The mechanism of free radical formation of KPS 12 Figure 1.7 Mechanism of pre-irradiation polymerization 13 Figure 1.8 Mechanism of direct irradiation polymerization 14 Figure 1.9 Effect of capillary number on residual oil saturation and oil recovery 15 Figure 1.10 Water breakthrough can be delayed and sweep efficiency improved by increasing the viscosity of the injected fluid with polymer 16 Figure 1.11 Acrylamide powder (a), structure of acrylamide (b) and polyacrylamide (c) 19 Figure 1.12 Reaction formula of hydrolysis of polyacrylamide 20 Figure 1.13 Structure of N-vinylpyrrolidone 21 Figure 1.14 Structure of graphene and graphene oxide 21 Figure 2.1 Synthesis procedure of GO 31 Figure 2.2 Shortened steps of the γ-ray induced free radical P(AM-NVP) copolymerization 32 Figure 2.3 Synthesis procedure of GO–P(AM-NVP) nanocomposite 34 Figure 3.1 P(AM-NVP) copolymers after purifying (a) and P(AM-PVP) copolymers disperse in brine (b) 37 Figure 3.2 Response surface of viscosity of 0.5 wt.% copolymers solution 41 Figure 3.3 FTIR spectra of (a) P(AM-NVP), (b) NVP and (c) AM 43 Figure 3.4 FTIR spectra of (a) GO–P(AM-NVP), (b) P(AM-NVP) and (c) GO 44 Figure 3.5 Raman spectra of (a) GO and (b) GO–P(AM-NVP) 46 iv Luan van Hoang Anh Quan – Master thesis Chapter 3: Results and Discussion Figure 3.10 Viscosity of (a) 0.5 wt.% P(AM-NVP) copolymers in brine annealed at 123 °C and (b) 1.0 wt.% GO–P(AM-NVP) nanocomposite in brine annealed at 135 °C during 31 days 51 Luan van Hoang Anh Quan – Master thesis Chapter 5: Conclusions and Recommendations Chapter Conclusions and Recommendations Chapt er 4: Conclus ions andRecom mendat ions 4.1 Conclusions The present study reported the completed procedure to obtain the copolymers and GO–copolymers nanocomposite, which can work for offshore reservoirs under high-temperature and high-salinity conditions The γ-ray induced copolymerization of the optimized acrylamide and Nvinylpyrrolidone monomer mixtures was successfully performed with high efficiency and allowed to obtain the thermostable P(AM-NVP) copolymers with easy-to-design properties, simplicity, low cost, and green for the environment The optimal conditions for copolymerization were obtained at 1.7 for AM/NVP monomer ratios and 23.2 wt.% for monomers concentration The obtained copolymers were then covalently coupled with graphene oxide (GO) synthesized from natural graphite using the modified Hummer’s method These properties suit to the required reservoir conditions and to scale up safely for producing the stable copolymers, which can be applied for EOR at high temperature (up to 123 °C) and high-salinity brine Moreover, we also found that 1.0 wt.% in brine dispersion of P(AM-NVP) covalently attached to partial rGO exhibited high stability in both viscosity and appearance during the annealing at 135 °C in 31 days As a result, the produced GO–P(AM-NVP) nanocomposite had excellent 52 Luan van Hoang Anh Quan – Master thesis dispersion Chapter 5: Conclusions and Recommendations stability in high-salinity and high-temperature conditions The advantageous properties of the P(AM-NVP) copolymers and GO–P(AM-NVP) nanocomposite possess the potential for EOR applications in high-tempera ture offshore reservoirs 4.2 Recommendations A closer study of how these nanocomposites alter the wettability of a rock surface and contact angle should be executed before and after annealing Measuring the interfacial tension (IFT) of the copolymers and GO–copolymers dispersions should be executed before and after annealing Modifying PAM copolymers structures with another monomer (not Nvinylpyrrolidone) should be studied 53 Luan van Hoang Anh Quan – Master thesis List of published papers related to learner LIST OF PUBLISHED PAPERS RELATED TO LEARNER Nguyen, T L., Hoang, A Q., Nguyen, P T., Luu, A T., Pham, D K., Dinh, V P., & Luong, T B (2021) STABLE DISPERSION OF GRAPHENE OXIDE–COPOLYMER NANOCOMPOSITE FOR ENHANCED OIL RECOVERY APPLICATION IN HIGHTEMPERATURE OFFSHORE RESERVOIRS Colloids and Surfaces A: Physicochemical and Engineering Aspects, 127343 54 Luan van Hoang Anh Quan – Master thesis References REFERENCES [1] Minqi Li, World energy 2017-2050: Annual report, Dep Econ Univ Utah 2050 (2017) 1–29 [2] Alexander H Tullo, The future of oil is in chemicals, not fuels, C&EN Glob Enterp 97 (2019) 26–29 https://doi.org/10.1021/CEN-09708-FEATURE2 [3] A Bahadori, Fundamentals of enhanced oil and gas recovery from conventional and unconventional 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Luan van Hoang Anh Quan – Master thesis Appendix APPENDIX A.1 Pictures of the equipments and instruments Figure A.1 Powersonic 603 Hwashin Technology Figure A.2 Drying/Oven – Shellap Figure A.3 Digital Temperature Control Hotplate with Magnetic Stirrer e Luan van Hoang Anh Quan – Master thesis Appendix Figure A.4 Ultrasonic Hielscher UP 100H Figure A.5 FreeZone 6L Benchtop Freeze Dry Systems Figure A.6 pH/ORP Mettler Hana HI 3220 f Luan van Hoang Anh Quan – Master thesis Appendix Figure A.7 Brookfield DV-III+ Programmable Rheometer Figure A.8 Stuart RE300 Rotary Evaporator Figure A.9 Fourier transform infrared spectroscopy (FT-IR) PerkinElmer frontier g Luan van Hoang Anh Quan – Master thesis Appendix Figure A.10 DSC-3/TGA Mettler Toledo Figure A.11 Raman Horiba Xplora One h Luan van Hoang Anh Quan – Master thesis Appendix A.2 Pictures of the softwares Figure A.12 StatGraphics 18–X64 software Figure A.13 Origin 8.5 software i Luan van Hoang Anh Quan – Master thesis Appendix + Figure A.14 Mendeley Desktop Figure A.15 MathType software j Luan van Hoang Anh Quan – Master thesis Appendix Figure A.16 Chemdraw Professional 16.0 software k Luan van ... of N-vinylpyrrolidone 1.3.2 Graphene oxide in EOR Figure 1.14 Structure of graphene and graphene oxide The conjugation of various high-viscosity polymers on graphene oxide nanosheets (GONs) has... N-vinylpyrrolidone PAM Polyvinylpyrrolidone APS Ammonium persulfate GO Graphene oxide rGO Reduced graphene oxide GONs Graphene oxide nanosheets NMP N-methylpyrrolidone RSM Response surface methodology... White Tiger P(AM-NVP) Poly(acrylamide-N-vinylpyrrolidone) copolymers GO–P(AM-NVP) P(AM-NVP) copolymers covalently couple with graphene oxide nanocomposite viii Luan van Hoang Anh Quan – Master thesis