Production of N-containing Chemicals and Materials from Biomass 12

This book is a collection of studies on state-of-art techniques developed for producing value-added N-containing chemicals and N-doped carbon materials from renewable sources via sustainable technologies. Aiming to improve conversion effectiveness and develop innovative techniques for new value-added N-containing products, topics in the text address recent advances, assess and highlight promising methods or technological strategies, and outline direct conversion routes for conversion of renewable resources to N-containing chemicals and materials. World-renowned authorities, experts, and professionals have contributed individual chapters in selected areas to cover the overall topic comprehensively. In addition to researchers and professionals in the field, educators teaching university courses on biomass transformation, biomass energy, energy materials, heterocyclic chemistry, resource materials and sustainable development and green chemistry will find the text informative with new international perspectives. Cover Biofuels and Biorefineries Series: Volume 12 Production of N-containing Chemicals and Materials from Biomass Copyright Preface Acknowledgments About the Book Contents Editors and Contributors Part I. Production of N-Containing Compounds by Chemical Catalytic Processes 1. Hydrolysis of Nitrile Compounds in Near-Critical Water 1.1 Introduction 1.2 Near-Critical Water 1.3 Nitrile Compounds 1.4 Hydrolysis Reaction of Typical Nitriles in NCW 1.4.1 Hydrolysis Reaction in NCW 1.4.2 Hydrolysis of Nitrile Compounds 1.4.2.1 Hydrolysis of Nitrile Compounds Catalyzed by Acid/Base Catalysts 1.4.2.2 Hydrolysis of Saturated and Unsaturated Nitriles in NCW 1.4.2.3 Hydrolysis of Aliphatic and Aromatic Nitriles in NCW 1.4.2.4 Hydrolysis Reaction of Heterocyclic Nitriles in NCW 1.4.2.5 Hydrolysis Reaction of Dicyan-Nitriles in NCW 1.4.3 Comparison of Hydrolysis Reactions of Different Nitrile Compounds in NCW 1.4.4 Factors Affecting Hydrolysis of Nitrile Compounds in NCW 1.4.4.1 Reaction Temperature and Time 1.4.4.2 Reaction Pressure 1.4.4.3 Catalytic Additives 1.5 Conclusions and Future Outlook References 2. Major Advances in Syntheses of Biomass Based Amines and Pyrrolidone Products by Reductive Amination Process of Majo... 2.1 Introduction 2.2 Reductive Amination of FUR and HMF 2.3 Reductive Amination of LA 2.4 Conclusions and Future Outlook References 3. Producing N-Heterocyclic Compounds from Lignocellulosic Biomass Feedstocks 3.1 Introduction 3.2 Five-Membered N-Heterocyclic Compounds 3.2.1 Pyrrolidines 3.2.2 1-Ethyl-2-(Ethylideneamino)-5-Methylpyrrolidin-2-Ol 3.2.3 Pyrrolidones 3.2.4 Bicyclic and Fused Pyrrolidones 3.2.5 Pyrroles 3.2.6 Pyrazoles 3.2.7 Imidazoles 3.2.8 Tetrazoles 3.3 Six-Membered N-Heterocyclic Compounds 3.3.1 Pyridinium Salts 3.3.2 Pyridazin-3(2H)-One 3.3.3 Pyridazines 3.3.4 Pyrazines 3.4 Quinolines 3.5 Benzodiazepinones 3.6 Pyrido[2,3-d]Pyrimidines 3.7 1,2,4-Triazine, Quinoxaline and Pyrazolo[3,4-b]Quinoxaline 3.8 Conclusion and Future Outlook References 4. Waste Shell Biorefinery: Sustainable Production of Organonitrogen Chemicals 4.1 Waste Shell Biorefinery 4.1.1 Global Shell Waste Generation 4.1.2 The Ocean-Based Chitin Biomass 4.1.3 Chitin Extraction from Shell Waste 4.2 Chitin Hydrolysis into the Amino- or Amide-Sugar Products 4.2.1 Water Solvent Systems 4.2.2 Organic or Co-solvent Systems 4.3 Chitin Oxidation into Amino Acids 4.3.1 Amino Acids 4.3.2 Oxidation of Chitin Monomers to Produce Amino Acid Sugars 4.3.2.1 Oxidative Cleavage of Chitin Monomer to Produce Short-chain Amino Acids 4.3.2.2 Oxidation of Chitin/Chitosan into Amino Acids 4.4 Chitin Dehydration into Furanic Amide (3A5AF) 4.4.1 Potential of 3A5AF as a Building Block Chemical 4.4.2 Chitin Monomer Dehydration to 3A5AF 4.4.3 Chitin Polymer Dehydration to 3A5AF 4.5 Other Transformation Strategies 4.5.1 Hydrothermal Methods 4.5.2 Hydrogenation/Hydrogenolysis Reactions 4.5.3 Condensation Reactions 4.6 Concluding Remarks and Future Outlook References 5. Sustainable Production of Nitriles from Biomass 5.1 Introduction 5.2 Bio-Based Nitriles Production from Renewable Nitrogen Sources 5.3 Bio-Based Nitriles Production from Renewable Oxygenates 5.3.1 Acrylonitrile 5.3.2 Acetonitrile 5.3.3 Fatty Nitriles 5.3.4 Furan Nitriles 5.3.5 Aromatic Nitriles 5.4 Conclusions and Future Outlook References 6. Catalytic Upgrading of Bio-Based Ketonic Acids to Pyrrolidones with Hydrogen Donor Sources 6.1 Introduction to Reductive Amination of Levulinic Acid (LA) 6.2 Hydrogen Gas 6.2.1 Noble Metal-Based Catalysts 6.2.2 Non-noble Metal-Based Catalysts 6.3 Formic Acid 6.4 Ammonium Formate 6.5 Hydrosilane 6.6 Boron Hydride 6.7 Conclusions and Outlook References Part II. Production of N-Containing Compounds via Biological Processes 7. Microbial Production of Amine Chemicals from Sustainable Substrates 7.1 Metabolic Engineering for the Production of Amino Acids as N-Containing Building Blocks 7.1.1 l-Glutamate 7.1.2 l-Lysine 7.1.3 Production of Other l-Aspartate Family Amino Acids 7.1.4 l-Tryptophan 7.2 Extending the Metabolic Pathways of Amino Acid Biosynthesis 7.2.1 Value-Added N-Containing Chemicals Derived from l-Glutamate 7.2.1.1 Putrescine 7.2.1.2 GABA 7.2.1.3 5-Aminolevulinic acid 7.2.1.4 l-Theanine 7.2.1.5 N-Methylglutamate 7.2.2 Value-Added N-Containing Chemicals Derived from l-Lysine 7.2.2.1 Cadaverine 7.2.2.2 5-Aminovalerate 7.2.2.3 l-Pipecolic Acid 7.2.2.4 Ectoine and Hydroxyectoine 7.2.2.5 l-Carnitine 7.2.3 Value-Added N-Containing Chemicals Derived from l-Tryptophan 7.2.3.1 Violacein 7.2.3.2 Hydroxytryptophan, Serotonin and Melatonin 7.2.3.3 Anthranilate and N-Methylanthranilate 7.2.3.4 Chlorinated Tryptophan 7.2.3.5 Brominated Tryptophane and Tyrian Purple 7.2.3.6 Brominated Indoles and Tryptamines 7.2.4 Value-Added N-Containing Chemicals Derived from l-Isoleucine 7.2.4.1 4-Hydroxyisoleucine 7.3 Microbial Production of N-Containing Compounds from Renewable Substrates 7.3.1 Wood/Plant-Derived Substrates 7.3.1.1 Starch 7.3.1.2 Cellulose 7.3.1.3 Xylose 7.3.1.4 Arabinose 7.3.2 Agricultural Residues 7.3.3 Side Streams from Industrial Processes 7.3.3.1 Glycerol 7.3.3.2 Spent Sulfite Liquor 7.3.3.3 Amino Sugars 7.3.3.4 Residues from Food and Beverage Production 7.3.4 Methanol as Representative C1 Substrate 7.3.5 Marine Resources 7.4 Perspectives for the Microbial Production of N-Containing Compounds 7.4.1 Trending Approaches in Metabolic Engineering 7.4.2 Expanding the Substrate Spectra 7.4.3 Expanding the Product Portfolio 7.5 Conclusion and Future Outlook References Part III. Application of N-containing Biomass to Manufacture of Chemicals and Materials 8. Engineering Biochar-Based Materials for Carbon Dioxide Adsorption and Separation 8.1 Introduction 8.2 Recent Advances in Using Biochar as an Adsorbent for Carbon Capture 8.3 Key Engineering Strategies Targeting Biochar for Carbon Dioxide Adsorption and Separation 8.3.1 Strategies for Modifying the Physical Properties of Biochar 8.3.1.1 Increasing the Specific Surface Area 8.3.1.2 Increasing Pore Volume and Optimising Pore Size 8.3.1.3 Developing a Hierarchical Pore Structure 8.3.2 Strategies for Functionalizing Biochar for High-Performance CO2 Adsorption and Separation 8.3.2.1 Introducing Basic Functional Groups 8.3.2.2 Introducing Oxygenated Functional Groups 8.3.2.3 Loading Alkaline and Alkaline Earth Metals 8.3.3 Summary 8.4 Challenges and Perspectives 8.5 Conclusions and Future Outlook References 9. Producing N-Containing Chemicals from Biomass for High Performance Thermosets 9.1 Introduction 9.2 Overview of Nitrogen-Containing Compounds Derived from Renewable Platform Chemicals 9.2.1 Nitrogenous Compounds Derived from Nitrogen-Free Biobased Platform Compounds 9.2.1.1 From Vanillin 9.2.1.2 From Guaiacol 9.2.1.3 Furan-Derived Nitrogen-Containing Compounds 9.2.2 Nitrogenous Biomass Found in Nature 9.2.2.1 Chitin 9.2.2.2 Amino Acid 9.3 Bio-based Nitrogen-Containing Epoxy Resin 9.3.1 Heat Resistant Bio-based Epoxy Resin 9.3.2 Intrinsically Flame-Retardant Bio-based Epoxy Resin 9.3.3 Toughening of Bio-based Epoxy Resins 9.3.4 Biodegradable and Recycled Bio-based Epoxy Resin 9.3.5 Bio-based Epoxy Resins with Other Functions 9.4 Bio-based Nitrogen-Containing Benzoxazine Resin 9.4.1 Bio-based Benzoxazines with High Thermal Property 9.4.2 Bio-based Benzoxazines with Flame Retardancy 9.4.3 Bio-based Benzoxazines with Antibacterial and Algaecidal Properties 9.4.4 Bio-based Benzoxazine Resins with Other Functions 9.5 Other Bio-based Nitrogen-Containing Thermosetting Resins 9.5.1 Bio-based Phthalonitrile Resin 9.5.2 Bio-based Polyurethane Resin 9.5.3 Bio-based Cyanate Ester Resin 9.6 Conclusions and Perspectives References 10. Preparation of N-Doped Carbon Materials from Lignocellulosic Biomass Residues and Their Application to Energy Stor... 10.1 Introduction 10.2 Synthetic Routes for the Preparation of N-Doped Carbon Materials 10.2.1 Post-synthesis Strategies 10.2.2 In Situ Strategies 10.3 Nitrogen-Doped Carbon Materials Derived from Lignocellulosic Biomass Residues in Energy-Related Applications 10.3.1 Electrocatalytic and Catalytic Applications 10.3.2 Electrodes in Supercapacitors 10.4 Summary and Outlook References 11. Preparation of Green N-Doped Biochar Materials with Biomass Pyrolysis and Their Application to Catalytic Systems 11.1 Introduction 11.2 Preparation Methods of Nitrogen-Doped Biochar 11.3 Chemical Activation and Nitrogen Doping During Biomass Pyrolysis for Nitrogen-Doped Biochar 11.3.1 Nitrogen Doping Process During Biomass Pyrolysis 11.3.2 Chemical Activation Process During Biomass Pyrolysis 11.3.3 Simultaneous Pyrolysis, Activation, and Nitrogen Doping of Biomass 11.4 Biomass Catalytic Pyrolysis with Nitrogen-Doped Biochar Catalyst 11.4.1 Effect of the Catalytic Pyrolysis Process 11.4.2 Effect of Active Functional Groups in Catalyst 11.4.3 Effect of Pore Structure in Catalyst 11.4.4 Effect of Biomass Composition 11.5 Conclusions and Future Outlook References Part IV. N Transformations During Thermal Processes 12. Evaluating the Role of Gasification Stages on Evolution of Fuel-N to Deepen in Sustainable Production of NH3 12.1 Introduction 12.2 Materials and Methods 12.2.1 Materials: MBM Characterization 12.2.2 Pyrolysis and Gasification Experiments 12.2.3 Characterization of N-Containing Products 12.2.4 Stage Contribution to Final Fuel-N Distribution 12.3 Results 12.3.1 MBM Characterization 12.3.2 Fuel-N Distribution Obtained in Pyrolysis Stage 12.3.3 Characterization of Tar Obtained in Pyrolysis Experiments 12.3.4 Fuel-N Distribution Obtained from Char Gasification Stage 12.3.5 Contribution of Each Stage to Final Fuel-N Distribution 12.4 Conclusions and Future Outlook 12.4.1 Conclusions 12.4.2 Future Outlook References Index