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Chemical Catalysts for Biomass Upgrading


Chemical Catalysts for Biomass Upgrading


1. Aufl.

von: Mark Crocker, Eduardo Santillan-Jimenez

142,99 €

Verlag: Wiley-VCH
Format: EPUB
Veröffentl.: 27.11.2019
ISBN/EAN: 9783527814800
Sprache: englisch
Anzahl Seiten: 640

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Beschreibungen

A comprehensive reference to the use of innovative catalysts and processes to turn biomass into value-added chemicals Chemical Catalysts for Biomass Upgrading offers detailed descriptions of catalysts and catalytic processes employed in the synthesis of chemicals and fuels from the most abundant and important biomass types. The contributors?noted experts on the topic?focus on the application of catalysts to the pyrolysis of whole biomass and to the upgrading of bio-oils. The authors discuss catalytic approaches to the processing of biomass-derived oxygenates, as exemplified by sugars, via reactions such as reforming, hydrogenation, oxidation, and condensation reactions. Additionally, the book provides an overview of catalysts for lignin valorization via oxidative and reductive methods and considers the conversion of fats and oils to fuels and terminal olefins by means of esterification/transesterification, hydrodeoxygenation, and decarboxylation/decarbonylation processes. The authors also provide an overview of conversion processes based on terpenes and chitin, two emerging feedstocks with a rich chemistry, and summarize some of the emerging trends in the field. This important book: -Provides a comprehensive review of innovative catalysts, catalytic processes, and catalyst design -Offers a guide to one of the most promising ways to find useful alternatives for fossil fuel resources -Includes information on the most abundant and important types of biomass feedstocks -Examines fields such as catalytic cracking, pyrolysis, depolymerization, and many more Written for catalytic chemists, process engineers, environmental chemists, bioengineers, organic chemists, and polymer chemists, Chemical Catalysts for Biomass Upgrading presents deep insights on the most important aspects of biomass upgrading and their various types.
Preface xiii 1 Upgrading of Biomass via Catalytic Fast Pyrolysis (CFP) 1Charles A. Mullen 1.1 Introduction 1 1.1.1 Catalytic Pyrolysis Over Zeolites 4 1.1.1.1 Catalytic Pyrolysis Over HZSM-5 4 1.1.1.2 Deactivation of HZSM-5 During CFP 9 1.1.1.3 Modification of ZSM-5 with Metals 13 1.1.1.4 Modifications of ZSM-5 Pore Structure 18 1.1.2 CFP with Metal Oxide Catalysts 20 1.1.3 CFP to Produce Fine Chemicals 24 1.1.4 Outlook and Conclusions 26 References 27 2 The Upgrading of Bio-Oil via Hydrodeoxygenation 35Adetoyese O. Oyedun, Madhumita Patel, Mayank Kumar, and Amit Kumar 2.1 Introduction 35 2.2 Hydrodeoxygenation (HDO) 37 2.2.1 Hydrodeoxygenation of Phenol as a Model Compound 38 2.2.1.1 HDO of Phenolic (Guaiacol) Model Compounds 38 2.2.1.2 HDO of Phenolic (Anisole)Model Compounds 40 2.2.1.3 HDO of Phenolic (Cresol) Model Compounds 40 2.2.2 Hydrodeoxygenation of Aldehyde Model Compounds 41 2.2.3 Hydrodeoxygenation of Carboxylic Acid Model Compounds 43 2.2.4 Hydrodeoxygenation of Alcohol Model Compounds 44 2.2.5 Hydrodeoxygenation of Carbohydrate Model Compounds 44 2.3 Chemical Catalysts for the HDO Reaction 45 2.3.1 Catalyst Promoters for HDO 48 2.3.2 Catalyst Supports for HDO 49 2.3.3 Catalyst Selectivity for HDO 49 2.3.4 Catalyst Deactivation During HDO 50 2.4 Research Gaps 51 2.5 Conclusions 52 Acknowledgments 52 References 53 3 Upgrading of Bio-oil via Fluid Catalytic Cracking 61Idoia Hita, Jose Maria Arandes, and Javier Bilbao 3.1 Introduction 61 3.2 Bio-oil 63 3.2.1 Bio-oil Production via Fast Pyrolysis 63 3.2.2 General Characteristics, Composition, and Stabilization of Bio-oil 63 3.2.2.1 Adjustment of Bio-oil Composition Through Pyrolytic Strategies 65 3.2.2.2 Bio-oil Stabilization 66 3.2.3 Valorization Routes for Bio-oil 69 3.2.3.1 Hydroprocessing 69 3.2.3.2 Steam Reforming 70 3.2.3.3 Extraction of Valuable Components from Bio-oil 71 3.3 Catalytic Cracking of Bio-oil: Fundamental Aspects 71 3.3.1 The FCC Unit 71 3.3.2 Cracking Reactions and Mechanisms 73 3.3.3 Cracking of Oxygenated Compounds 74 3.3.4 Cracking of Bio-oil 76 3.4 Bio-oil Cracking in the FCC Unit 78 3.4.1 Cracking of Model Oxygenates 78 3.4.2 Coprocessing of Oxygenates and Their Mixtures with Vacuum Gas Oil (VGO) 78 3.4.3 Cracking of Bio-oil and Its Mixtures with VGO 79 3.5 Conclusions and Critical Discussion 86 References 88 4 Stabilization of Bio-oil via Esterification 97Xun Hu 4.1 Introduction 97 4.2 Reactions of the Main Components of Bio-Oil Under Esterification Conditions 102 4.2.1 Sugars 102 4.2.2 Carboxylic Acids 109 4.2.3 Furans 113 4.2.4 Aldehydes and Ketones 114 4.2.5 Phenolics 116 4.2.6 Other Components 117 4.3 Processes for Esterification of Bio-oil 121 4.3.1 Esterification of Bio-oil Under Subcritical or Supercritical Conditions 121 4.3.2 Removal of the Water in Bio-oil to Enhance Conversion of Carboxylic Acids 121 4.3.3 In-line Esterification of Bio-oil 123 4.3.4 Esterification Coupled with Oxidation 123 4.3.5 Esterification Coupled with Hydrogenation 123 4.3.6 Steric Hindrance in Bio-oil Esterification 124 4.3.7 Coking in Esterification of Bio-oil 125 4.3.8 Effects of Bio-oil Esterification on the Subsequent Hydrotreatment 129 4.4 Catalysts 132 4.5 Summary and Outlook 136 Acknowledgments 137 References 137 5 Catalytic Upgrading of Holocellulose-Derived C5 and C6 Sugars 145Xingguang Zhang, Zhijun Tai, Amin Osatiashtiani, Lee Durndell, Adam F. Lee, and Karen Wilson 5.1 Introduction 145 5.2 Catalytic Transformation of C5–C6 Sugars 146 5.2.1 Isomerization Catalysts 147 5.2.1.1 Zeolites 149 5.2.1.2 Hydrotalcites 151 5.2.1.3 Other Solid Catalysts 154 5.2.2 Dehydration Catalysts 154 5.2.2.1 Zeolitic and Mesoporous Brønsted Solid Acids 156 5.2.2.2 Sulfonic Acid Functionalized Hybrid Organic–Inorganic Silicas 159 5.2.2.3 Metal–Organic Frameworks 163 5.2.2.4 Supported Ionic Liquids 164 5.2.3 Catalysts for Tandem Isomerization and Dehydration of C5–C6 Sugars 165 5.2.3.1 Bifunctional Zeolites and Mesoporous Solid Acids 165 5.2.3.2 Metal Oxides, Sulfates, and Phosphates 167 5.2.3.3 Metal–Organic Frameworks 172 5.2.4 Catalysts for the Hydrogenation of C5–C6 Sugars 172 5.2.4.1 Ni Catalysts 173 5.2.4.2 Ru Catalysts 176 5.2.4.3 Pt Catalysts 178 5.2.4.4 Other Hydrogenation Catalysts 178 5.2.5 Hydrogenolysis Catalysts 179 5.2.6 Other Reactions 183 5.3 Conclusions and Future Perspectives 184 References 186 6 Chemistry of C—C Bond Formation Reactions Used in Biomass Upgrading: Reaction Mechanisms, Site Requirements, and Catalytic Materials 207Tuong V. Bui, Nhung Duong, Felipe Anaya, Duong Ngo, Gap Warakunwit, and Daniel E. Resasco 6.1 Introduction 207 6.2 Mechanisms and Site Requirements of C–C Coupling Reactions 208 6.2.1 Aldol Condensation: Mechanism and Site Requirement 208 6.2.1.1 Base-Catalyzed Aldol Condensation 208 6.2.1.2 Acid-Catalyzed Aldol Condensation: Mechanism and Site Requirement 214 6.2.2 Alkylation: Mechanism and Site Requirement 219 6.2.2.1 Lewis Acid-Catalyzed Alkylation Mechanism 219 6.2.2.2 Brønsted Acid-Catalyzed Alkylation Mechanism 220 6.2.2.3 Base-Catalyzed Alkylation: Mechanism and Site Requirement 225 6.2.3 Hydroxyalkylation: Mechanism and Site Requirement 225 6.2.3.1 Brønsted Acid-Catalyzed Mechanism 227 6.2.3.2 Site Requirement 228 6.2.4 Acylation: Mechanism and Site Requirement 229 6.2.4.1 Mechanistic Aspects of Acylation Reactions 230 6.2.4.2 Role of Brønsted vs. Lewis Acid in Acylation Over Zeolites 232 6.2.5 Ketonization: Mechanism and Site Requirement 234 6.2.5.1 Mechanism of Surface Ketonization 234 6.2.5.2 Site Requirement 238 6.3 Optimization and Design of Catalytic Materials for C–C Bond Forming Reactions 239 6.3.1 Oxides 239 6.3.1.1 Magnesia (MgO) 239 6.3.1.2 Zirconia (ZrO2) 245 6.3.2 Zeolites 248 6.3.2.1 ZSM-5 248 6.3.2.2 HY 254 6.3.2.3 HBEA 257 References 259 7 Downstream Conversion of Biomass-Derived Oxygenates to Fine Chemicals 299Michele Besson, Stephane Loridant, Noemie Perret, and Catherine Pinel 7.1 Introduction 299 7.2 Selective Catalytic Oxidation 300 7.2.1 Introduction 300 7.2.2 Catalytic Oxidation of Glycerol 301 7.2.2.1 Glycerol to Glyceric Acid (GLYAC) 301 7.2.2.2 Glycerol to Tartronic Acid (TARAC) 304 7.2.2.3 Glycerol to Dihydroxyacetone (DHA) 305 7.2.2.4 Glycerol to Mesoxalic Acid (MESAC) 305 7.2.2.5 Glycerol to Glycolic Acid (GLYCAC) 305 7.2.2.6 Glycerol to Lactic Acid (LAC) 306 7.2.3 Oxidation of 5-Hydroxymethylfurfural (HMF) 307 7.2.3.1 HMF to 2,5-Furandicarboxylic Acid (FDCA) 307 7.2.3.2 HMF to 2,5-Diformylfuran (DFF) 309 7.2.3.3 HMF to 5-Hydroxymethyl-2-furancarboxylic Acid (HMFCA) or 5-Formyl-2-furancarboxylic Acid (FFCA) 310 7.3 Hydrogenation/Hydrogenolysis 310 7.3.1 Introduction 310 7.3.2 Hydrogenolysis of Polyols 310 7.3.2.1 Hydrodeoxygenation of Polyols 311 7.3.2.2 C–C Hydrogenolysis of Polyols 314 7.3.3 Hydrogenation of Carboxylic Acids 316 7.3.3.1 Levulinic Acid 316 7.3.3.2 Succinic Acid 318 7.3.4 Selective Hydrogenation of Furanic Compounds 320 7.3.5 Reductive Amination of Acids and Furans 323 7.4 Catalyst Design for the Dehydration of Biosourced Molecules 324 7.4.1 Introduction 324 7.4.2 Glycerol to Acrolein 325 7.4.3 Lactic Acid to Acrylic Acid 328 7.4.4 Sorbitol to Isosorbide 330 7.5 Conclusions and Outlook 331 References 331 8 Conversion of Lignin to Value-added Chemicals via Oxidative Depolymerization 357Justin K. Mobley 8.1 Introduction 357 8.1.1 Cautionary Statements 360 8.2 Catalytic Systems for the Oxidative Depolymerization of Lignin 361 8.2.1 Enzymes and Bio-mimetic Catalysts 361 8.2.2 Cobalt Schiff Base Catalysts 363 8.2.3 Vanadium Catalysts 367 8.2.4 Methyltrioxorhenium (MTO) Catalysts 368 8.3 Commercial Products from Lignin 369 8.4 Stepwise Depolymerization of ?-O-4 Linkages 369 8.4.1 Benzylic Oxidation 369 8.4.2 Secondary Depolymerization 376 8.5 Heterogeneous Catalysts for Lignin Depolymerization 382 8.6 Outlook 386 Acknowledgments 386 References 386 9 Lignin Valorization via Reductive Depolymerization 395Yang (Vanessa) Song 9.1 Introduction 395 9.2 Late-stage Reductive Lignin Depolymerization 396 9.2.1 Mild Hydroprocessing 398 9.2.2 Harsh Hydroprocessing 404 9.2.3 Bifunctional Hydroprocessing 407 9.2.4 Liquid Phase Reforming 410 9.2.5 Reductive Lignin Depolymerization Using Hydrosilanes, Zinc, and Sodium 414 9.3 Reductive Catalytic Fractionation (RCF) 416 9.3.1 Reaction Conditions 417 9.3.2 Lignocellulose Source 417 9.3.3 Applied Catalyst 427 9.4 Outlook 428 Acknowledgment 429 References 429 10 Conversion of Lipids to Biodiesel via Esterification and Transesterification 439Amin Talebian-Kiakalaieh and Amin Nor Aishah Saidina 10.1 Introduction 439 10.2 Different Feedstocks for Biodiesel Production 441 10.3 Biodiesel Production 441 10.3.1 Algal Biodiesel Production 442 10.3.1.1 Nutrients for Microalgae Growth 443 10.3.1.2 Microalgae Cultivation System 444 10.3.1.3 Harvesting 444 10.3.1.4 Drying 445 10.3.1.5 Lipid Extraction 446 10.4 Catalytic Transesterification 446 10.4.1 Homogeneous Catalysts 446 10.4.1.1 Alkali Catalysts 446 10.4.1.2 Acid Catalysts 448 10.4.1.3 Two-step Esterification–Transesterification Reactions 448 10.4.2 Heterogeneous Catalysts 450 10.4.2.1 Solid Acid Catalysts 451 10.4.2.2 Solid Base Catalysts 451 10.4.3 Enzyme-Catalyzed Transesterification Reactions 453 10.5 Supercritical Transesterification Processes 454 10.6 Alternative Processes for Biodiesel Production 455 10.6.1 Ultrasonic Processes 455 10.6.2 Microwave-Assisted Processes 456 10.7 Summary 459 References 459 11 Upgrading of Lipids to Hydrocarbon Fuels via (Hydro)deoxygenation 469David Kubi?ka 11.1 Introduction 469 11.2 Feedstocks 471 11.3 Chemistry 472 11.4 Technologies 475 11.5 Catalysts 477 11.5.1 Sulfided Catalysts 477 11.5.2 Metallic Catalysts 480 11.5.3 Metal Carbide, Nitride, and Phosphide Catalysts 483 11.6 Conclusions and Outlook 489 References 490 12 Upgrading of Lipids to Fuel-like Hydrocarbons and Terminal Olefins via Decarbonylation/Decarboxylation 497Ryan Loe, Eduardo Santillan-Jimenez, and Mark Crocker 12.1 Introduction 497 12.2 Lipid Feeds 500 12.3 deCOx Catalysts: Active Phases 502 12.4 deCOx Catalysts: Support Materials 508 12.5 Reaction Conditions 509 12.6 Reaction Mechanism 511 12.7 Catalyst Deactivation 516 12.8 Conclusions and Outlook 518 References 518 13 Conversion of Terpenes to Chemicals and Related Products 529Anne E. Harman-Ware 13.1 Introduction 529 13.2 Terpene Biosynthesis and Structure 529 13.3 Sources of Terpenes 532 13.3.1 Conifers and Other Trees 532 13.3.2 Essential Oils and Other Extracts 534 13.4 Isolation of Terpenes 535 13.4.1 Tapping and Extraction 535 13.4.2 Terpenes as a By-product of Pulping Processes 536 13.5 Historical Uses of Raw Terpenes 536 13.5.1 Adhesives and Turpentine 536 13.5.2 Flavors, Fragrances, Therapeutics, and Pharmaceutical Applications 537 13.6 Catalytic Methods for Conversion of Terpenes to Fine Chemicals and Materials 537 13.6.1 Homogeneous Processes 538 13.6.1.1 Hydration and Oxidation Reactions 538 13.6.1.2 Homogeneous Catalysis for the Epoxidation of Monoterpenes 541 13.6.1.3 Isomerizations 541 13.6.1.4 Production of Terpene Carbonates from CO2 and Epoxides 543 13.6.1.5 Polymers and Other Materials from Terpenes 545 13.6.1.6 “Click Chemistry” Routes for the Production of Materials and Medicinal Compounds from Terpenes 548 13.6.2 Heterogeneous Processes 551 13.6.2.1 Isomerization and Hydration of ?-Pinene 551 13.6.2.2 Heterogeneous Catalysts for the Epoxidation of Monoterpenes 553 13.6.2.3 Isomerization of ?-Pinene Oxide 555 13.6.2.4 Vitamins from Terpenes 555 13.6.2.5 Dehydrogenation and Hydrogenation Reactions of Terpenes 557 13.6.2.6 Conversion of Terpenes to Fuels 558 Acknowledgments 560 References 561 14 Conversion of Chitin to Nitrogen-containing Chemicals 569Xi Chen and Ning Yan 14.1 Waste Shell Biorefinery 569 14.2 Production of Amines and Amides from Chitin Biomass 571 14.2.1 Sugar Amines/Amides 571 14.2.2 Furanic Amines/Amides 574 14.2.3 Polyol Amines/Amides 576 14.3 Production of N-heterocyclic Compounds from Chitin Biomass 579 14.4 Production of Carbohydrates and Acetic Acid from Chitin Biomass 581 14.5 Production of Advanced Products from Chitin Biomass 584 14.6 Conclusion 587 References 587 15 Outlook 591Eduardo Santillan-Jimenez and Mark Crocker Index 599
Mark Crocker is Associate Director at the University of Kentucky Center for Applied Energy Research, where he leads the Biofuels and Environmental Catalysis research program, and Professor of Chemistry at the University of Kentucky. Eduardo Santillan-Jimenez is Principal Research Scientist at the University of Kentucky Center for Applied Energy Research. His current work focuses on the application of heterogeneous catalysis to the production of renewable fuels and chemicals.
A comprehensive reference to the use of innovative catalysts and processes to turn biomass into value-added chemicals Chemical Catalysts for Biomass Upgrading offers detailed descriptions of catalysts and catalytic processes employed in the synthesis of chemicals and fuels from the most abundant and important biomass types. The contributors—noted experts in the field—focus on the application of catalysts to the pyrolysis of whole biomass and to the upgrading of bio-oils. The authors also discuss catalytic approaches to the processing of biomass-derived oxygenates, as exemplified by sugars, via reactions such as reforming, hydrogenation, oxidation, and condensation. Additionally, this book provides an overview of catalysts for lignin valorization via oxidative and reductive methods and considers the conversion of fats and oils to fuels and terminal olefins by means of esterification/transesterification, hydrodeoxygenation, and decarboxylation/decarbonylation processes. The authors also provide an overview of conversion processes based on terpenes and chitin, two emerging feedstocks with a rich chemistry, and summarize some of the emerging trends in the field. This important book: Provides a comprehensive review of innovative catalysts, catalytic processes, and catalyst design Offers a guide to one of the most promising ways to find useful alternatives for fossil fuel resources Includes information on the most abundant and important types of biomass feedstocks Examines topics such as catalytic cracking, pyrolysis, depolymerization, and many more Written for catalytic chemists, process engineers, environmental chemists, bioengineers, organic chemists, and polymer chemists, Chemical Catalysts for Biomass Upgrading presents deep insights on the most important aspects of biomass upgrading.

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