Lignin and Lignans as Renewable Raw Materials – Chemistry, Technology and Applications

<p>Series Preface<br /><br />Preface xiii<br /><br />Acronyms xvii<br /><br />List of Symbols xxi<br /><br />Part One Introduction 1<br /><br />1 Background and overview 3<br /><br />1.1 Introduction 3<br /><br />1.2 Lignin: economical aspects and sustainability 4<br /><br />1.3 Structure of the book 5<br /><br />References 8<br /><br />Part Two What is lignin? 9<br /><br />2 Structure and physicochemical properties 11<br /><br />2.1 Introduction 11<br /><br />2.2 Monolignols, the basis of a complex architecture 12<br /><br />2.3 Chemical classification of lignins 15<br /><br />2.4 Lignin linkages 19<br /><br />2.5 Structural models of native lignin 22<br /><br />2.6 Lignin–carbohydrate complex 37<br /><br />2.7 Physical and chemical properties of lignins 44<br /><br />References 48<br /><br />3 Detection and determination 53<br /><br />3.1 Introduction 53<br /><br />3.2 The detection of lignin (colour–forming reactions) 53<br /><br />3.3 Determination of lignin 59<br /><br />3.4 Direct methods for the determination of lignin 61<br /><br />3.5 Indirect methods for the determination of lignin 65<br /><br />3.6 Comparison of the different determination methods 72<br /><br />References 75<br /><br />4 Biosynthesis of lignin 81<br /><br />4.1 Introduction 81<br /><br />4.2 The biological function of lignins 82<br /><br />4.3 The shikimic acid pathway 82<br /><br />4.4 The phenylpropanoid pathway 85<br /><br />4.5 The biosynthesis of lignin precursors (the monolignol specific pathway) 86<br /><br />4.6 The dehydrogenation of the precursors 92<br /><br />4.7 Peroxidases and laccases 92<br /><br />4.8 The radical polymerisation 95<br /><br />4.9 The lignin–cabohydrate connectivity 109<br /><br />4.10 Location of lignins (cell walls lignification) 111<br /><br />4.11 Lignins from hybrids 112<br /><br />4.12 Differences between Angiosperm and Gymnosperm lignins 115<br /><br />References 119<br /><br />Part Three Sources and Characterization of Lignin 127<br /><br />5 Isolation of lignins 129<br /><br />5.1 Introduction 129<br /><br />5.2 Methods for lignin isolation from wood and grass for laboratory purposes 130<br /><br />5.3 Commercial lignins 143<br /><br />References 154<br /><br />6 Functional and spectroscopic characterization of lignins 161<br /><br />6.1 Introduction 161<br /><br />6.2 Elemental analysis and empirical formula 161<br /><br />6.3 Determination of molecular weight 163<br /><br />6.4 Functional group analyses 167<br /><br />6.5 Frequencies of functional groups and linkage types in lignins 176<br /><br />6.6 Characterization by spectroscopic methods 182<br /><br />6.7 Raman spectroscopy 186<br /><br />References 195<br /><br />7 Chemical characterization and modification of lignins 207<br /><br />7.1 Introduction 207<br /><br />7.2 Characterization by chemical degradation methods 207<br /><br />7.3 Other chemical transformations of lignins 238<br /><br />7.4 Other chemical modifications of lignins 247<br /><br />7.5 Thermolysis (pyrolysis) 249<br /><br />7.6 Biochemical transformations of lignins 250<br /><br />References 252<br /><br />Part Four Lignins Applications 267<br /><br />8 Applications of modified and unmodified lignins 269<br /><br />8.1 Introduction 269<br /><br />8.2 Lignin as fuel 272<br /><br />8.3 Lignin as a binder 273<br /><br />8.4 Lignin as chelant agent 275<br /><br />8.5 Lignin in biosciences and medicine 276<br /><br />8.6 Lignin in agriculture 278<br /><br />8.7 Polymers with unmodified lignin 279<br /><br />8.8 Other applications of unmodified lignins 288<br /><br />8.9 New polymeric materials derived from modified lignins and related biomass derivatives 294<br /><br />8.10 Polymers derived from chemicals obtainable from lignin decomposition 304<br /><br />8.11 Other applications of modified lignins 305<br /><br />References 308<br /><br />9 High–value chemical products 313<br /><br />9.1 Introduction 313<br /><br />9.2 Gasification: syngas from lignin 315<br /><br />9.3 Thermolysis of lignin 316<br /><br />9.4 Hydrodeoxygenation (hydrogenolysis) 317<br /><br />9.5 Hydrothermal hydrolysis 319<br /><br />9.6 Chemical depolymerisation 321<br /><br />9.7 Oxidative transformation of lignin 324<br /><br />9.8 High–value chemicals from lignin 328<br /><br />References 335<br /><br />Part Five Lignans 339<br /><br />10 Structure and chemical properties of lignans 341<br /><br />10.1 Introduction 341<br /><br />10.2 Structure and classification of lignans 341<br /><br />10.3 Nomenclature of lignans 346<br /><br />10.4 Lignan occurrence in plants 349<br /><br />10.5 Methods of isolation of lignans from plants 354<br /><br />10.6 Structure determination of lignans 356<br /><br />10.7 The chemical synthesis of lignans 357<br /><br />References 387<br /><br />11 Biological properties of lignans 401<br /><br />11.1 Introduction 401<br /><br />11.2 Biosynthesis of lignans 402<br /><br />11.3 Metabolism of lignans 413<br /><br />11.4 Plant physiology and plant defence 418<br /><br />11.5 Podophyllotoxin 422<br /><br />11.6 Biological activity of different lignan structures 435<br /><br />References 466<br /><br />Part Six Outcome and Challenges 491<br /><br />12 Summary, conclusions, and perspectives on lignin chemistry 493<br /><br />12.1 Sources of lignin 493<br /><br />12.2 On the structure of lignin 494<br /><br />12.3 Biosynthesis and biological function 495<br /><br />12.4 Applications of lignin 495<br /><br />12.5 Lignans 497<br /><br />12.6 Perspectives 498<br /><br />References 499<br /><br />General index 500<br /><br />Author index 501</p>
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