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電子書籍詳細


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バイオマス改質技術のための化学触媒

Chemical Catalysts for Biomass Upgrading

1

Crocker, Mark (EDT)   Santillan-Jimenez, Eduardo (EDT)

Wiley-VCH 2019/11
640p.
出版国: DE
ISBN: 9783527344666
eISBN: 9783527814800
KNPID: EY00369793
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Full Description

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.

Table of Contents

Preface xiii

1 Upgrading of Biomass via Catalytic Fast Pyrolysis (CFP) 1
Charles 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 35
Adetoyese 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 61
Idoia 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 97
Xun 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 145
Xingguang 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 207
Tuong 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 299
Michele 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 357
Justin 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 β-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 395
Yang (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 439
Amin 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 469
David Kubička

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 497
Ryan 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 529
Anne 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 α-Pinene 551

13.6.2.2 Heterogeneous Catalysts for the Epoxidation of Monoterpenes 553

13.6.2.3 Isomerization of α-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 569
Xi 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 591
Eduardo Santillan-Jimenez and Mark Crocker

Index 599