Cover -- Title Page -- Copyright -- Dedication -- Contents -- Series Preface -- Preface -- List of Acronyms -- List of Symbols -- Part I Introduction -- Chapter 1 Background and Overview -- 1.1 Introduction -- 1.2 Lignin: Economical Aspects and Sustainability -- 1.3 Structure of the Book -- References -- Part II What is Lignin? -- Chapter 2 Structure and Physicochemical Properties -- 2.1 Introduction -- 2.2 Monolignols, The Basis of a Complex Architecture -- 2.3 Chemical Classification of Lignins -- 2.4 Lignin Linkages -- 2.5 Structural Models of Native Lignin -- 2.5.1 Softwood Models -- 2.5.2 Hardwood Models -- 2.5.3 Herbaceous Plant Models -- 2.6 Lignin-Carbohydrate Complex -- 2.7 Physical and Chemical Properties of Lignins -- 2.7.1 Molecular Weight -- 2.7.2 Dispersity Index (Đ) -- 2.7.3 Thermal Properties -- 2.7.4 Solubility Properties -- References -- Chapter 3 Detection and Determination -- 3.1 Introduction -- 3.2 The Detection of Lignin (Color-Forming Reactions) -- 3.2.1 Reagents for Detecting Lignins -- 3.3 Determination of Lignin -- 3.4 Direct Methods for the Determination of Lignin -- 3.4.1 Methods for Lignin as a Residue -- 3.4.2 Lignin in Solution Methods -- 3.5 Indirect Methods for the Determination of Lignin -- 3.5.1 Chemical Methods -- 3.5.2 Spectrophotometric Methods -- 3.5.3 Methods Based on Oxidant Consumption -- 3.6 Comparison of the Different Determination Methods -- References -- Chapter 4 Biosynthesis of Lignin -- 4.1 Introduction -- 4.2 The Biological Function of Lignins -- 4.3 The Shikimic Acid Pathway -- 4.4 The Common Phenylpropanoid Pathway -- 4.5 The Biosynthesis of Lignin Precursors (the Monolignol-Specific Pathway) -- 4.5.1 The Biosynthesis of Other Monolignols -- 4.5.2 The Transport of Monolignols -- 4.6 The Dehydrogenation of the Precursors -- 4.7 Peroxidases and Laccases.

4.8 The Radical Polymerization -- 4.8.1 Dimerization -- 4.8.2 Quinone Methides -- 4.8.3 Lignification -- 4.8.4 Interunit Linkage Types -- 4.8.5 Dehydrogenation Polymer (DHP) -- 4.9 The Lignin-Carbohydrate Connectivity -- 4.10 Location of Lignins (Cell Wall Lignification) -- 4.11 Differences Between Angiosperm and Gymnosperm Lignins -- References -- Part III Sources and Characterization of Lignin -- Chapter 5 Isolation of Lignins -- 5.1 Introduction -- 5.2 Methods for Lignin Isolation from Wood and Grass for Laboratory Purposes -- 5.2.1 Lignin as Residue -- 5.2.2 Lignin by Dissolution -- 5.3 Commercial Lignins -- 5.3.1 Kraft Lignin -- 5.3.2 Sulfite Lignin (Lignosulfonate Process) -- 5.3.3 Soda Lignin (Alkali Lignin) -- 5.3.4 Organosolv Pulping -- 5.3.5 Other Methods of Separation of Lignin from Biomass -- References -- Chapter 6 Functional and Spectroscopic Characterization of Lignins -- 6.1 Introduction -- 6.2 Elemental Analysis and Empirical Formula -- 6.3 Determination of Molecular Weight -- 6.3.1 Gel-Permeation Chromatography (GPC) -- 6.3.2 Light Scattering -- 6.3.3 Vapor-Pressure Osmometry (VPO) -- 6.3.4 Ultrafiltration (UF) -- 6.4 Functional Group Analyses -- 6.4.1 Methoxyl Group (MeO) -- 6.4.2 Phenolic Hydroxyl Group (OH ph) -- 6.4.3 Total and Aliphatic Hydroxyl Groups (R-OH) -- 6.4.4 Ethylenic Groups (>C=CC=O) -- 6.4.6 Carboxyl Groups (-COO-) -- 6.4.7 Sulfonate Groups and Total Sulfur Composition (R-SO2O- and S) -- 6.5 Frequencies of Functional Groups and Linkage Types in Lignins -- 6.5.1 β-O-4' Linked Units -- 6.5.2 β-5' Linked Units -- 6.5.3 β-1' Linked Units -- 6.5.4 α-O-4' Linked Units (benzyl ethers) -- 6.5.5 Condensed and Uncondensed Units -- 6.5.6 Biphenyl Structures -- 6.5.7 4-O-5' Linked Units -- 6.5.8 β-2 and β-6 Linked Units -- 6.5.9 β-β Linked Units.

6.5.10 Dibenzodioxocin Units -- 6.6 Characterization by Spectroscopic Methods -- 6.6.1 Fourier Transform Infrared (FTIR) Spectroscopy -- 6.7 Raman Spectroscopy -- 6.7.1 Ultraviolet (UV) -- 6.7.2 NMR Spectroscopy -- 6.7.3 Other Spectroscopic Methods -- References -- Chapter 7 Chemical Characterization and Modification of Lignins -- 7.1 Introduction -- 7.2 Characterization by Chemical Degradation Methods -- 7.2.1 Oxidation with Nitrobenzene -- 7.2.2 Oxidation with Cupric Oxide -- 7.2.3 Permanganate Oxidation -- 7.2.4 Mild Hydrolysis -- 7.2.5 Acidolysis -- 7.2.6 Thioglycolic Acid Hydrolysis (Mercaptolysis) -- 7.2.7 Thioacetolysis -- 7.2.8 Thioacidolysis -- 7.2.9 Hydrogenolysis -- 7.2.10 Derivatization Followed by Reductive Cleavage (DFRC) -- 7.2.11 Nucleus-Exchange Reaction (NE) -- 7.2.12 Ozonolysis -- 7.2.13 Pyrolysis -- 7.3 Other Chemical Modifications of Lignins -- 7.3.1 Acylation -- 7.3.2 Alkylation -- 7.3.3 Halogenation -- 7.3.4 Nitration -- 7.3.5 Sulfonation -- 7.3.6 Oxidation -- 7.3.7 Other Modifications of Lignins -- 7.4 Thermolysis (Pyrolysis) of Lignins -- 7.5 Biochemical Transformations of Lignins -- 7.5.1 Biodegradation of Lignin -- 7.5.2 Enzyme-Based Oxidation of Lignin -- References -- Part IV Lignins Applications -- Chapter 8 Applications of Modified and Unmodified Lignins -- 8.1 Introduction -- 8.2 Lignin as Fuel -- 8.2.1 Combustion in the Paper Industry -- 8.2.2 Heating and Power -- 8.3 Lignin as a Binder -- 8.3.1 Coal Briquettes -- 8.3.2 Packing -- 8.3.3 Pelleted Feeds -- 8.4 Lignin as Chelating Agent -- 8.5 Lignin in Biosciences and Medicine -- 8.6 Lignin in Agriculture -- 8.7 Polymers with Unmodified Lignin -- 8.7.1 Phenol-Formaldehyde Binders -- 8.7.2 Polyolefin-Lignin Polymers -- 8.7.3 Polyester-Lignin Polymers -- 8.7.4 Acrylamide-Lignin Polymers -- 8.7.5 Polyurethane-Lignin Polymers.

8.7.6 Bioplastics (Liquid Wood) -- 8.7.7 Hydrogels -- 8.7.8 Foams and Composites -- 8.7.9 Conducting Polymers -- 8.8 Other Applications of Unmodified Lignins -- 8.8.1 Lignin in Lead-Acid Batteries -- 8.8.2 Lignin-Based Nanoparticles and Thin Films -- 8.8.3 Lignin in Dust Control -- 8.8.4 Lignin in Concrete Admixtures -- 8.8.5 Lignin as a Dispersant, Emulsifier, and Surfactant -- 8.8.6 Lignin as Floating Agent -- 8.9 New Polymeric Materials Derived from Modified Lignins and Related Biomass Derivatives -- 8.9.1 Modified Lignin in Phenol-Formaldehyde Wood Adhesives -- 8.9.2 Modified Lignins for Epoxy Resin Synthesis -- 8.9.3 Polyurethanes -- 8.9.4 Lignin-Polybutadiene Copolymers -- 8.10 Polymers Derived from Chemicals Obtainable from Lignin Decomposition -- 8.11 Other Applications of Modified Lignins -- 8.11.1 Nanoparticles (NPs) -- 8.11.2 Cationic Amphiphilic Lignin Derivatives -- 8.11.3 Soil Preservation -- 8.11.4 Fertilizers -- References -- Chapter 9 High-Value Chemical Products -- 9.1 Introduction -- 9.2 Gasification: Syngas from Lignin -- 9.3 Thermolysis of Lignin -- 9.4 Hydrodeoxygenation (Hydrogenolysis) -- 9.5 Hydrothermal Hydrolysis -- 9.6 Chemical Depolymerization -- 9.6.1 Acid Media Depolymerization -- 9.6.2 Base Media Depolymerization -- 9.6.3 Ionic Liquid-Assisted Depolymerization -- 9.6.4 Supercritical Fluids-Assisted Depolymerization -- 9.7 Oxidative Transformation of Lignin -- 9.7.1 Oxidation with Chlorinated Reagents -- 9.7.2 Oxidation with Ozone -- 9.7.3 Oxidation with Hydrogen Peroxide -- 9.7.4 Oxidation with Peroxy Acids -- 9.7.5 Catalytic Oxidation -- 9.8 High-Value Chemicals from Lignin -- 9.8.1 Vanillin -- 9.8.2 Dimethyl Sulfide and Dimethylsulfoxide -- 9.8.3 Active Carbon -- 9.8.4 Carbon Fiber -- References -- Part V Lignans.

Chapter 10 Structure and Chemical Properties of Lignans -- 10.1 Introduction -- 10.2 Structure and Classification of Lignans -- 10.2.1 Lignans -- 10.2.2 Hybrid Lignans -- 10.3 Nomenclature of Lignans -- 10.4 Lignan Occurrence in Plants -- 10.5 Methods of Determination and Isolation of Lignans from Plants -- 10.5.1 Lipid Extraction -- 10.5.2 Solvent Extraction -- 10.5.3 Separation by Precipitation -- 10.5.4 Chromatographic Methods -- 10.5.5 Extraction of Polar Lignans from Biological Materials -- 10.6 Structure Determination of Lignans -- 10.7 The Chemical Synthesis of Lignans -- 10.7.1 Generalities on the Asymmetric Total Synthesis of Lignans -- 10.7.2 Dibenzylbutane Lignans -- 10.7.3 Dibenzylbutyrolactone Lignans -- 10.7.4 Cyclolignans (Aryltetralin Lignans) -- 10.7.5 Dibenzocyclooctadiene Lignans -- References -- Chapter 11 Biological Properties of Lignans -- 11.1 Introduction -- 11.2 Biosynthesis of Lignans -- 11.2.1 Pinoresinol Synthase (Dirigent Protein) -- 11.2.2 The General Biosynthetic Pathway of Lignans -- 11.2.3 Other Biosynthetic Pathways of Lignans -- 11.2.4 Biosynthetic Pathways for Neolignans -- 11.2.5 Biosynthetic Pathways for Norlignans -- 11.3 Metabolism of Lignans -- 11.4 Plant Physiology and Plant Defense -- 11.5 Podophyllotoxin -- 11.5.1 Extraction, Synthesis, and Biotechnological Approaches -- 11.5.2 Biological Activities of PPT -- 11.5.3 The Action Mechanism of PPT -- 11.5.4 Congeners and Derivatives (Other Aryltetralin Lactones) -- 11.6 Biological Activity of Different Lignan Structures -- 11.6.1 Dibenzylbutane Lignans -- 11.6.2 Dibenzylbutyrolactone Lignans -- 11.6.3 Dibenzylbutyrolactol Lignans -- 11.6.4 Furanoid Lignans -- 11.6.5 Furofuranoid Lignans -- 11.6.6 Aryltetralin Lignans (No Lactones) -- 11.6.7 Arylnaphthalene Lignans -- 11.6.8 Dibenzocyclooctadiene Lignans -- 11.6.9 Neolignans.

11.6.10 Hybrid Lignans.