Nanoporous Catalysts for Biomass Conversion

Edited by Feng-Shou Xiao, Zhejiang University, Hangzhou, China Liang Wang, Zhejiang University, Hangzhou, China Series Editor Christian Stevens, Faculty of Bioscience Engineering, Ghent University, Belgium

• List of Contributors xiiiSeries Preface xviiAcknowledgements xix1 Nanoporous Organic Frameworks for Biomass Conversion 1Xiang Zhu, Chi-Linh Do-Thanh, and Sheng Dai1.1 Introduction 11.2 Nanoporous Crystalline Organic Frameworks 41.2.1 Metal–Organic Frameworks 41.2.2 Covalent Organic Frameworks 101.3 Nanoporous Organic Sulfonated Resins 111.3.1 Amberlyst Resins 111.3.2 Nafion Resins 111.4 Conclusions and Perspective 13References 132 Activated Carbon and Ordered Mesoporous Carbon-Based Catalysts for Biomass Conversion 17Xiaochen Zhao, Jifeng Pang, Guangyi Li, Fei Liu, Jinming Xu, Mingyuan Zheng, Ning Li, Changzhi Li, Aiqin Wang, and Tao Zhang2.1 Introduction 172.2 Activated Carbon and Mesoporous Carbon 182.2.1 Preparation of Activated Carbon and Mesoporous Carbon 182.2.2 Properties of Carbon in Catalysis 192.2.3 Functionalization of Carbon Materials 202.3 Cellulose Conversion 212.3.1 Cellulose Hydrolysis 212.3.2 Conversion of Cellulose to Hexitols 272.3.3 Conversion of Cellulose to Glycols 302.3.4 Conversion of Cellulose to Other Important Chemicals 322.4 Lignin Conversion 332.4.1 Hydrogenolysis (Hydrocracking) 342.4.2 Hydrodeoxygenation (HDO) 352.4.3 Hydrogenation and Ethanolysis 382.5 Synthesis of Biofuel (Diesel or Jet Fuel) from Lignocellulose 392.5.1 C–C Coupling Reactions 402.5.2 Hydrodeoxygenation (HDO) 422.6 Summary 46References 463 Nanoporous Carbon/Nitrogen Materials and their Hybrids for Biomass Conversion 55Hui Su, Hong-Hui Wang, Tian-Jian Zhao, and Xin-Hao Li3.1 Introduction 553.2 Dehydrogenation of Formic Acid 573.2.1 Mono-Metallic Nanoparticle/Carbon–Nitrogen Nanocomposites: Metal-Support Effect 573.2.2 Bimetallic Nanoparticle/Carbon–Nitrogen Nanocomposites 593.2.3 Trimetallic Nanoparticle/Carbon–Nitrogen Nanocomposites 593.2.4 Core–Shell Nanostructure/Carbon–Nitrogen Nanocomposites 603.2.5 Reduction of Carbon Dioxide to Formic Acid Using Carbon/Nitrogen Materials 613.3 Transfer Hydrogenation of Unsaturated Compounds from Formic Acid 643.4 Synthesis of High-Value-Added Chemicals from Biomass 673.5 Metal-Free Catalyst: Graphene Oxide for the Conversion of Fructose 713.6 Conclusions and Outlook 72References 734 Recent Developments in the Use of Porous Carbon Materials for Cellulose Conversion 79Abhijit Shrotri, Hirokazu Kobayashi, and Atsushi Fukuoka4.1 Introduction 794.2 Overview of Catalytic Cellulose Hydrolysis 814.3 Functionalized Carbon Catalyst for Cellulose Hydrolysis 844.3.1 Synthesis and Properties of Carbon Catalysts 844.3.2 Sulfonated Carbon Catalyst for Cellulose Hydrolysis 854.3.3 Oxygenated Carbon Catalyst for Cellulose Hydrolysis 874.3.4 Mechanistic Aspects of Carbon-Catalyzed Cellulose Hydrolysis 904.4 Summary and Outlook 93References 945 Ordered Mesoporous Silica-Based Catalysts for Biomass Conversion 99Liang Wang, Shaodan Xu, Xiangju Meng, and Feng-Shou Xiao5.1 Introduction 995.2 Sulfated Ordered Mesoporous Silicas 1005.2.1 Conversion of Levulinic Acid to Valerate Esters 1005.2.2 One-Pot Conversion of Cellulose into Chemicals 1015.2.3 Dehydration of Xylose to Furfural 1045.3 Ordered Mesoporous Silica-Supported Polyoxometalates and Sulfated Metal Oxides 1065.4 Heteroatom-Doped Ordered Mesoporous Silica 1085.4.1 Al-Doped Mesoporous Silica 1085.4.2 Sn-Doped Mesoporous Silica 1085.5 Ordered Mesoporous Silica-Supported Metal Nanoparticles 1095.5.1 Mesoporous Silica-Supported Pd Nanoparticles 1105.5.2 Mesoporous Silica-Supported Pt Nanoparticles 1115.5.3 Mesoporous Silica-Supported Ni Nanoparticles 1115.6 Overall Summary and Outlook 113References 1156 Porous Polydivinylbenzene-Based Solid Catalysts for Biomass Transformation Reactions 127Fujian Liu and Yao Lin6.1 Introduction 1276.2 Synthesis of Porous PDVB-Based Solid Acids and Investigation of their Catalytic Performances 1296.2.1 Sulfonic Group-Functionalized Porous PDVB 1296.2.2 Sulfonic Group-Functionalized Porous PDVB-SO3HSO2CF3 1326.2.3 PDVB-Based Porous Solid Bases for Biomass Transformation 1336.2.4 Strong Acid Ionic Liquid-Functionalized PDVB-Based Catalysts 1356.2.5 Cooperative Effects in Applying both PDVB-Based Solid Acids and Solid Bases for Biomass Transformation 1416.3 Perspectives of PDVB-Based Solid Catalysts and their Application for Biomass Transformations 144Acknowledgments 144References 1457 Designing Zeolite Catalysts to Convert Glycerol, Rice Straw, and Bio-Syngas 149Chuang Xing, Guohui Yang, Ruiqin Yang, and Noritatsu Tsubaki7.1 Glycerol Conversion to Propanediols 1497.1.1 Introduction 1497.1.2 Mechanisms of Propanediol Synthesis 1517.1.3 Zeolite Catalysts for Propanediol Synthesis 1527.1.4 Conclusions and Outlook 1567.2 Rice Straw Hydrogenation 1567.2.1 Introduction 1567.2.2 Direct Conversion of Rice Straw into Sugar Alcohol Through In-Situ Hydrogen 1577.2.3 Conclusions and Outlook 1597.3 Bio-Gasoline Direct Synthesis from Bio-Syngas 1597.3.1 Introduction 1597.3.2 Biomass Gasification to Bio-Syngas 1607.3.3 Representative FT Gasoline Synthesis System 1617.3.4 FT Gasoline Synthesis Catalysts 1637.3.5 Conclusions and Outlook 168References 1698 Depolymerization of Lignin with Nanoporous Catalysts 177Zhicheng Luo, Jiechen Kong, Liubi Wu, and Chen Zhao8.1 Introduction 1778.2 Developed Techniques for Lignin Depolymerization 1788.2.1 Heterogeneous Noble Metal Catalyst System in the Presence of Hydrogen 1788.2.2 Heterogeneous Transition Metal Catalyst System in the Presence of Hydrogen 1838.2.3 Homogeneous Catalyst System for Lignin Depolymerization in the Presence of H2 1878.2.4 Cleavage of C–O Bonds in Lignin with Metals and Hydrogen-Donor Solvents in the Absence of Hydrogen 1888.3 Oxidative Depolymerization of Lignin 1908.3.1 Metal-Supported Oxide Catalysts 1918.3.2 Polyoxometalate Catalysts 1958.3.3 Organometallic Catalysts 1968.3.4 Ionic Liquid Catalysts 1978.4 Hydrolysis of Lignin with Base and Acid Catalysts 1988.5 Other Depolymerization Techniques (Cracking, Photocatalysis, Electrocatalysis, and Biocatalysis) 2008.6 Conclusions 202Acknowledgments 203References 2039 Mesoporous Zeolite for Biomass Conversion 209Liang Wang, Shaodan Xu, Xiangju Meng, and Feng-Shou Xiao9.1 Introduction 2099.2 Production of Biofuels 2109.2.1 Pyrolysis of Biomass 2109.2.2 Upgrading of Pyrolysis Oil 2119.2.3 Conversion of Lipids into Alkane Oil 2179.2.4 Synthesis of Ethyl Levulinate Biofuel 2189.3 Conversion of Glycerol 2209.3.1 Dehydration of Glycerol 2209.3.2 Etherification of Glycerol 2219.3.3 Aromatization of Glycerol 2239.4 Overall Summary and Outlook 224References 22510 Lignin Depolymerization Over Porous Copper-Based Mixed-Oxide Catalysts in Supercritical Ethanol 231Xiaoming Huang, Tamás I. Korányi, and Emiel J. M. Hensen10.1 Introduction 23110.1.1 Hydrotalcites 23110.1.2 Lignin Depolymerization 23310.2 Lignin Depolymerization by CuMgAl Mixed-Oxide Catalysts in Supercritical Ethanol 23410.2.1 Effect of Catalyst and Ethanol Solvent 23610.2.2 Influence of Reaction Parameters and Lignin Source 24010.2.3 Effect of Catalyst Composition 24210.3 Conclusions 246References 24811 Niobium-Based Catalysts for Biomass Conversion 253Qineng Xia and Yanqin Wang11.1 Introduction 25311.2 Hydrolysis 25511.3 Dehydration 25711.3.1 Sorbitol Dehydration 25711.3.2 Carbohydrate Dehydration 25811.3.3 Glycerol Dehydration 26111.4 HMF Hydration to Levulinic Acid 26511.5 Hydrodeoxygenation 26611.6 C–C Coupling Reactions 27211.7 Esterification/Transesterification 27211.8 Other Reactions in Biomass Conversion 27311.8.1 Delignification 27311.8.2 Ring-Opening of GVL 27311.8.3 Steam Reforming Reaction 27411.8.4 Ketalization 27411.9 Summary and Outlook 274References 27512 Towards More Sustainable Chemical Synthesis, Using Formic Acid as a Renewable Feedstock 283Shu-Shuang Li, Lei Tao, Yong-Mei Liu, and Yong Cao12.1 Introduction 28312.2 General Properties of FA and Implications for Green Synthesis 28512.3 Transformation of Bio-Based Platform Chemicals 28612.3.1 Reductive Transformation Using FA as a Hydrogen Source 28612.3.2 Tandem Transformation Using FA as a Versatile Reagent 29112.4 FA-Mediated Depolymerization of Lignin or Chitin 29212.4.1 Lignin Depolymerization using FA 29212.4.2 Chitin Depolymerization using FA 29512.5 Upgrading of Bio-Oil and Related Model Compounds 29612.6 FA as the Direct Feedstock for Bulk Chemical Synthesis 29712.7 Conclusions and Outlook 300References 300Index 307