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Hydrophobic Guar Gum Derivatives Prepared by Controlled Grafting

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Hydrophobic Guar Gum Derivatives Prepared by Controlled Grafting Louisiana State University LSU Digital Commons LSU Doctoral Dissertations Graduate School 2005 Hydrophobic guar gum derivatives prepared by controlled grafting processes for hydraulic facturing applications Ahmad Bahamdan Louisiana State University and Agricultural and Mechanical College, [email protected] Follow this and additional works at: https://digitalcommons.lsu.edu/gradschool_dissertations Part of the Chemistry Commons Recommended Citation Bahamdan, Ahmad, "Hydrophobic guar gum derivatives prepared by controlled grafting processes for hydraulic facturing applications" (2005). LSU Doctoral Dissertations. 3384. https://digitalcommons.lsu.edu/gradschool_dissertations/3384 This Dissertation is brought to you for free and open access by the Graduate School at LSU Digital Commons. It has been accepted for inclusion in LSU Doctoral Dissertations by an authorized graduate school editor of LSU Digital Commons. For more information, please [email protected]. HYDROPHOBIC GUAR GUM DERIVATIVES PREPARED BY CONTROLLED GRAFTING PROCESSES FOR HYDRAULIC FRACTURING APPLICATIONS A Dissertation Submitted to the Graduate Faculty of the Louisiana State University and Agricultural and Mechanical College in partial fulfillment of the requirements for the degree of Doctor of Philosophy In The Department of Chemistry by Ahmad Bahamdan B.S., King Fahd University of Petroleum and Minerals, Saudi Arabia, 1989 M.S., University of Arkansas at Little Rock, AR, 1995 August 2005 ACKNOWLEDGEMENTS First of all I would like to express my sincere appreciation to my advisor and mentor, Professor William H. Daly, for his kindness, guidance, and encouragement during the entire course of this work. His encouragement, advices, patience helped me going through the difficulties and crises I met during the path of this work. I would like to thank everyone who has contributed to this work. And I would like to thank my committee members: Prof. Ioan Negulescu, Prof. Gudrun Schmidt, Prof. David Spivak, and Prof. Douglas Harrison for reviewing my work and making valuable suggestions and critical comments. I would also like to extend my appreciation to Prof. Daly research group members for their support and friendship. I am truly grateful to my parents, wife, children, and whole family for their support, prayers, and best wishes. I was fortunate to receive a scholarship from Saudi Aramco to pursue my higher education. I would like to appreciate and thank Saudi Aramco for their support and I would like to express my thanks to my Saudi Aramco advisor Mr. Brad Brumfield and every one who assisted me to achieve my goal. ii TABLE OF CONTENTS ACKNOWLEDGEMENTS ………………………………………………………………ii LIST OF TABLES ………………………………………………………………………..v LIST OF FIGURES ……………………………………………………………………...vi ABSTRACT..……………………………………………………………………………...x CHAPTER 1. INTRODUCTION ………………………………………………………...1 1.1 Background ……………………………………………………………………….1 1.2 Principal of Hydraulic Fracturing Process……………………………………….. 2 1.3 The Composition of Fracturing Fluids ……………………………………………4 1.3.1 Guar Gum……...…………………………………………………………….4 1.3.2 Guar Gum Derivatives ………...…………………………………………....6 1.3.3 Hydrophobically Modified Guar Gum ...……………………………………7 1.3.4 The Crosslinking Agent …………………...………………………………..9 1.3.5 Gel Breakers ………...……………………………………………………..13 1.4 This Project………………………………………………………………………14 CHAPTER 2. SYNTHESIS AND CHARACTERIZATION OF CARBOXYMETHYL GUAR……………………………………………………………………………………17 2.1 Introduction………………………………………………………………………17 2.2 Experimental Procedures………………………………………………………...18 2.2.1 Preparation of Sodium Carboxymethyl Guar (NaCMG) From CAA …......18 2.2.2 Preparation of Sodium Carboxymethyl Guar (NaCMG) From SCA .……..19 2.2.3 Conversion of NaCMG to The Acid From………………………………...20 2.2.4 Determination of The Degree of Substitution via Titration……………......20 2.2.5 NMR Analysis of CMG-Triton B Salt …………………………………….21 2.3 Result and Discussion……………………………………………………………21 2.3.1 Preparation of Sodium Carboxymethyl Guar (NaCMG) From CAA and SCA………………………………………………………………………...21 2.3.2 Degree of Substitution (D.S.) Determination …...………………………...22 2.3.3 NMR Analysis of CMG-Triton B Salt………………...…………………...25 CHAPTER 3. GRAFT COPOLYMERIZATION OF GUAR GUM VIA XANTHATE AND RAFT PROCESSES……………………………………………………………….29 3.1 Introduction………………………………………………………………………29 3.2 Reversible Addition-Fragmentation Chain Transfer (RAFT)……………………31 3.3 Experimental Procedure …………………………………………………………35 3.3.1 Reagent and Solvents…………………………………………………...….35 3.3.2 Guar Gum Activation Process……………………………………………..35 3.3.3 Guar Gum Xanthate Graft Copolymerization……………………………...36 3.3.4 Synthesis of RAFT Agent………………………………………………….37 iii 3.3.5 Graft Polymerization of Acrylic Acid (AA) onto Guar Gum via RAFT Process…………………………………………………………………......37 3.3.6 Graft Polymerization of MMA onto Guar Gum via RAFT Process……….38 3.4 Result and Discussion……………………………………………………………38 3.4.1 Synthesis of Guar Gum Grafts Utilizing RAFT and Xanthates…...……….38 CHAPTER 4. SYNTHESIS AND CHARACTERIZATION OF THE POLYOXYALKYLENEAMINES-GUAR GUM DERIVATIVES...…………………..44 4.1 Introduction………………………………………………………………………44 4.2 Experimental Procedures………………………………………………………...45 4.2.1 Reagents and Solvents…………………………………………...………...45 4.2.2 Preparation of Methyl Carboxymethyl Guar (MCMG)………………..…..45 4.2.3 Polyoxyalkyleneamines Derivatives …………………………………...….46 4.3 Results and Disscussion………………………………………………………….47 4.3.1 Preparation of Methyl Carboxymethyl Guar (MCMG)…………………....47 4.3.2 Synthesis of CMG and CMHPG Polyoxyalkyleneamines Derivatives…....47 4.3.3 Characterization of Guar Gum Grafted Products…………………………..52 4.3.4 Determination of Graft Percentage via NMR………………………...……55 4.3.5 Viscosity Determination……………………………………..…….………59 CHAPTER 5. VISCOSITY TRENDS OF THE CROSSLINKED GELS…….………..63 5.1 Introduction………………………………………………………………………63 5.2 Experimental Procedure………………………………………………………….64 5.2.1 Instrumentation and Viscosity Calaculation…………………...…………..64 5.2.2 Viscosity Measurements………………………………………...…………66 5.3 Results and Discussion…………………………………………………………..67 5.3.1 Carboxymethylated Guar Derivatives (BMCMGGW45)………………….68 5.3.2 Carboxymethylhydroxypropyl Guar Derivatives (BM12CMHPG)……….74 5.3.3 Carboxymethylhydroxypropyl Guar Derivatives (BM13CMHPG)……….78 5.3.4 Gel Strength………………………………………………………………..82 5.3.5 Summary…………………………………………………………………...88 CHAPTER 6. GEL BREAKING………………………………………………………...92 6.1 Introduction………………………………………………………………………92 6.2 Experimental Procedure………………………………………………………….92 6.3 Results and Discussion…………………………………………………………..93 CHAPTER 7. SUMMARY AND FUTURE WORK…………………………………..102 7.1 Conclusions …………………………………………………………………….102 7.2 Future Work…………………………………………………………………….104 REFERENCES…………………………………………………………………………107 VITA……………………………………………………………………………………110 iv LIST OF TABLES Table 1.1: Guar gum substitution patterns ………………………………………………..7 Table 2.1: Carboxymethyl guar produced with varying amounts of NaOH and CAA…..24 Table 2.2: Carboxymethyl guar produced with varying amounts of NaOH and SCA ….24 Table 2.3: Degree of substitution of commercial products determined by titration …….24 Table 2.4: CMG D.S. values calculated from triton B-NMR method versus the values calculated from titration …………………………………………………………………28 Table 4.1: Name and structure of different polyoxyalkyleneamines used in this study…50 Table 4.2: Percent yield, degree of substitution, (D.S.) and graft percentage of grafted CMHPG products………………………………………………………………………..58 Table 4.3: Percent yield, degree of substitution, (D.S.) and graft percentage of grafted CMG products……………………………………………………………………………59 Table 4.4: Brookfield viscosity of the base material compared to the grafted derivatives at room temperature, 0.48% solutions, and 20 RPM……………………………………….61 Table 4.5: Fann 35A viscosity of the base material compared to the grafted derivatives at room temperature, 0.48% solutions, and 60 RPM……………………………………….62 Table 5.1: Average viscosity of crosslinked BMCMGGW-45 control sample and its derivatives (37.7/s, 2.4g/L, pH >10, 0.4ml of Zr crosslinking agent)…………………...71 Table 5.2: Average viscosity of crosslinked BMCMGGW-45 control sample and its derivatives (37.7/s, 4.8g/L, pH >10, 0.5ml of Zr crosslinking agent)…………………...74 Table 5.3: Average viscosity of crosslinked BM12CMHPG control sample and its derivatives (37.7/s, 2.4g/L, pH >10, 0.4ml of Zr crosslinking agent)…………………...77 Table 5.4: Average viscosity of crosslinked BM12CMHPG control sample and its derivatives (37.7/s, 4.8g/L, pH >10, 0.5ml of Zr crosslinking agent)…………………...77 Table 5.5: Average viscosity of crosslinked BM13CMHPG control sample and its derivatives (37.7/s, 2.4g/L, pH >10, 0.4ml of Zr crosslinking agent)…………………...81 Table 5.6: Average viscosity of crosslinked BM13CMHPGcontrol sample and its derivatives (37.7/s, 4.8g/L, pH >10, 0.5ml of Zr crosslinking agent)…………………...81 v LIST OF FIGURES Figure 1.1: Photo shows the Cyamopsis tetragonoloba seed envelop, the seeds, the split seed and the grounded seed and different products of guar gum………………………….5 Figure 1.2: Basic chemical structure of guar gum………………………………………...6 Figure 1.3: Scheme shows the equilibrium of borate ion complexation with cis-hydroxy pairs on a Guar Gum molecule leading to the formation of gel………………………….11 Figure 1.4: Hydrogen-bonding mechanism for zirconium-guar………………………... 13 Figure 1.5: Covalent bonding mechanism for zirconium-guar………………………......13 Figure 2.1: FT-IR spectra of guar gum compared CMG ………………………………..23 Figure 2.2: NMR spectrum of BMCMGGW45-Triton B derivative in D2O ……………26 Figure 2.3: NMR spectrum
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