Lignin Chemistry (eBook)

Luis Serrano, Rafael Luque, Bert F. Sels (Herausgeber)

eBook Download: PDF

2020 | 1st ed. 2020
VI, 271 Seiten
Springer International Publishing (Verlag)
978-3-030-00590-0 (ISBN)

Infos

The series Topics in Current Chemistry Collections presents critical reviews from the journal Topics in Current Chemistry organized in topical volumes. The scope of coverage is all areas of chemical science including the interfaces with related disciplines such as biology, medicine and materials science. The goal of each thematic volume is to give the non-specialist reader, whether in academia or industry, a comprehensive insight into an area where new research is emerging which is of interest to a larger scientific audience.

Each review within the volume critically surveys one aspect of that topic and places it within the context of the volume as a whole. The most significant developments of the last 5 to 10 years are presented using selected examples to illustrate the principles discussed. The coverage is not intended to be an exhaustive summary of the field or include large quantities of data, but should rather be conceptual, concentrating on the methodological thinking that will allow the non-specialist reader to understand the information presented. Contributions also offer an outlook on potential future developments in the field.

The chapter 'Lignin-Based Composite Materials for Photocatalysis and Photovoltaics' is available open access under a CC BY 4.0 License via link.springer.com.

Professor Rafael Luque

Rafael Luque is Deputy Head of Department from Departamento de Quimica Organica at Universidad de Cordoba, where he graduated in 2005. With a postdoctoral stay of three years at the Green Chemistry Center of Excellence, The University of York (With Prof. James Clark), Prof. Luque has a significant experience on biomass and waste valorisation practises to materials, fuels and chemicals as well as nanoscale chemistry and green engineering.

Prof. Luque has published over 300 research articles, filed 3 patent applications and edited 10 books as well as numerous contributions to book chapters and invited, guest, keynote and plenary lectures in scientific events worldwide. He is also heavily involved in Chemical Education and promoting Science in Developing Countries. Among recent awards, Rafael received the Marie Curie Prize from Instituto Andaluz de Quimica Fina in Spain (2011), the Green Talents award from the Federal Ministry of Education and Research in Germany (2011), the TR35 Spain from Technology Review and MIT as one of the top 10 young entrepreneurs in Spain (2012), the RSC Environment, Sustainability and Energy Early Career Award (2013) from the Royal Society of Chemistry UK and the 2015 Lu Jiaxi lectureship from the College of Chemistry and Engineering in Xiamen University (China).

Dr. Luis Serrano

Luis Serrano is Ramon y Cajal Fellow in the Chemical Engineering Department of the University of Cordoba (Spain). He received his PhD in Chemical Engineering from University of Cordoba.

Previously, he got a post-doctoral grant in the University of the Basque Country (Spain) and a Juan de la Cie

rva grant in the same university. From 2015 to 2017, he was working in the Centre National de la Recherche Scientifique (France), one of the most recognized institutions around the world, as advanced researcher collaborating in two important national projects about cellulose and lignin. Moreover, he held visiting appointments at important research centers in Brazil, Portugal, Argentina, Tunisia, Chile and Italy.

His expertise is the biorefinery concept of lignocellulosic biomass including: the extraction, purification and depolymerization of lignin to produce chemicals; new uses of cellulose fibers (adsorbents, composites, special papers, etc.); nanocellulose production and functionalization; extraction, purification and transformation of hemicelluloses to added value products; and direct conversion of biomass to poyols as precursors of polyurethane foams.

During this period, he has published more than 60 scientific papers in high impact journals; he has collaborated in 28 R&D&I projects funded in competitive calls and 6 R&D&I projects with companies; he has co-directed 1 doctoral thesis, 4 master project thesis and 3 final career projects.

Professor Bert Sels

Bert F. Sels (1972), currently full professor at KU Leuven (Belgium), obtained his Ph.D. in 2000 in the field of heterogeneous oxidation catalysis under guidance of professor Pierre Jacobs. He was awarded the DSM Chemistry Award in 2000, the Incentive Award by the Belgian Chemical Society in 2005, and the international Green Chemistry Award in 2015. He is currently director of the Centre for Surface Chemistry and Catalysis (COK), and active in designing heterogeneous catalysts for future challenges in industrial organic and environmental catalysis. His expertise includes heterogeneous catalysis in bio-refineries, design of hierarchical zeolites and carbons for biomass conversion, and the spectroscopic and kinetic study of the active sites. He is co-chair of the Catalysis Commission of the International Zeolite Association (IZA) and co-founder of European Research Institute of Catalysis (ERIC). He is also member of the European Academy of Sciences and Arts, member of the international advisory board of ChemSusChem (Wiley) and ChemCatChem (Wiley) and associate editor of ACS Sustainable Chemistry & Engineering.

Inhalt

Contents 6
Lignin-Based Composite Materials for Photocatalysis and Photovoltaics 8
Abstract 8
1 Introduction 10
2 Native Versus Processed Lignin 12
2.1 Sources 12
2.2 Classification of Lignin 12
2.3 Extraction of Lignin 13
2.3.1 Sulfite Process 13
2.3.2 Soda Process 13
2.3.3 Kraft Process 14
2.3.4 Organosolv Process 14
2.4 Properties of Lignin 14
3 General Applications of Lignin 16
3.1 Synthesis of Materials from Lignin 16
4 Overview of Carbon-Based Materials in Photocatalysis and Photovoltaics 17
4.1 Lignin-Based Composites in Photocatalysis 19
4.1.1 Preparation Techniques of Lignin-Based Composite Photocatalyst 19
4.1.2 Chemical Interaction Between Lignin and Semiconductor 22
4.1.3 Applications of Lignin-Based Composites in Photocatalysis 24
4.2 Applications of Lignin-Based Materials in Photovoltaics 30
5 Conclusions, Future Perspectives, and Challenges 34
Acknowledgements 35
References 35
Degradation of Vanillin During Lignin Valorization Under Alkaline Oxidation 39
Abstract 39
1 Introduction 40
2 Methods 41
2.1 Materials 41
2.2 Alkaline Oxidation 41
2.3 Analysis Methods 42
2.3.1 High-Performance Liquid Chromatography (HPLC) 42
2.3.2 Liquid Chromatography–Electrospray Mass Spectrometry (LC–MS) 42
2.3.3 Gel Permeation Chromatography (GPC) 43
2.3.4 Gas Chromatography–Mass Spectrometer (GC–MS) 43
2.3.5 Heteronuclear Single Quantum Coherence (2D HSQC NMR) 43
2.3.6 Calculation Formulas 43
3 Results and Discussion 44
3.1 Alkaline Oxidation of Pine Lignin 44
3.2 Alkaline Oxidation of Vanillin 45
3.2.1 Temperature 46
3.2.2 Time 48
3.2.3 Stirring Speed, O2 Pressure, and Alkali Concentration 48
3.2.4 Catalyst 48
3.3 Analysis of Unknown Products 49
3.4 Presumable Mechanism of Vanillin Degradation 53
4 Conclusions 54
Acknowledgements 55
References 55
Perspective on Lignin Oxidation: Advances, Challenges, and Future Directions 58
Abstract 58
1 Introduction 58
2 Overview of Lignin Oxidation Research 59
2.1 Oxidation of Dimeric Model Compounds 59
2.1.1 Oxidative Cleavage of Non-oxidized Dimeric Structures 60
2.1.2 Oxidation of Side-Chain Alcohol Groups in Dimeric Structures 62
2.1.3 Cleavage of Oxidized Dimeric Structures 63
2.2 Oxidation of Isolated Lignin Substrates 64
3 Challenges in Lignin Oxidation 65
3.1 Substrate-Related Challenges 66
3.2 Catalyst- and Process-Related Challenges 67
4 Future Directions 68
Acknowledgements 69
References 69
Thermosetting Polymers from Lignin Model Compounds and Depolymerized Lignins 74
Abstract 74
1 Introduction 75
2 Lignin Model Compounds 76
2.1 Epoxy Resins 77
2.2 Polyurethanes 81
2.3 Phenol-Formaldehyde Resins—Polybenzoxazines 83
2.4 Other Polymeric Materials 84
3 Depolymerized Lignin Bio-oils 87
3.1 Epoxy Resins 87
3.2 Polyurethanes 91
3.3 PF Resins 93
4 Conclusion and Perspectives 93
Acknowledgments 94
References 94
Carbon Materials from Technical Lignins: Recent Advances 99
Abstract 99
1 Introduction 100
2 Carbon fibers 101
2.1 Lignin–lignin blends 102
2.2 Lignin–cellulose blends 103
2.3 Reinforcement 103
2.4 Fractionation 103
2.5 Chemical modification 104
2.5.1 Acetylation 104
2.5.2 Iodine pretreatment 104
2.6 New types of lignin 104
3 Carbon adsorbents 105
3.1 Carbonization 105
3.2 Physical activation 106
3.3 Chemical activation 107
3.4 Template Synthesis 112
3.5 Hydrothermal Carbonization 113
4 Porous CF 114
4.1 Carbonization 114
4.2 Physical Activation 115
4.3 Chemical Activation 115
5 Carbon Catalysts 115
5.1 Esterification 116
5.2 Cellulose Hydrolysis 116
5.3 Ethyl Tert-Butyl Ether Synthesis (Etherification) 117
5.4 Decomposition of 2-Propanol 118
6 Electrodes for Electrochemical Applications 120
6.1 Hydrogen Electrosorption 120
6.2 Electrical Double Layer Capacitors (EDLC) 120
6.3 Li-Ion Batteries 122
6.4 Na-Ion Batteries 123
7 Other Carbon Materials 123
7.1 Graphitic Carbons 123
7.2 Glassy Carbon 123
7.3 Carbon Black 124
8 Conclusions 124
Acknowledgements 125
References 125
Catalytic Strategies Towards Lignin-Derived Chemicals 133
Abstract 133
1 Introduction 134
2 Lignocellulosic Biomass 135
3 Lignin Chemistry During Biomass Fractionation 137
3.1 Base-Catalyzed Fractionation 138
3.1.1 Application and Mechanism 138
3.1.2 Kraft Pulping 139
3.1.3 Sulphite Pulping 140
3.1.4 Soda Pulping 140
3.2 Acid-Catalyzed Fractionation 140
3.2.1 Application and Mechanism 140
3.2.2 Concentrated Acid Hydrolysis (CAH) 142
3.2.3 Dilute Acid Hydrolysis (DAH) 142
3.3 (Aqueous) Organosolv Fractionation 143
4 Are Traditional Lignin Streams a Promising Feedstock for the Production of Chemicals? 143
4.1 Considerations on the Isolation and Analysis of Lignin 144
4.2 Depolymerization of Traditional Lignin 145
4.2.1 Reductive Depolymerization 145
4.2.2 Oxidative Depolymerization 146
4.2.3 Acid- or Base-Catalyzed Depolymerization 147
4.2.4 Solvolytic Depolymerization 148
4.2.5 Thermal Depolymerization Through Fast-Pyrolysis 148
4.3 Closing Remarks on Traditional Lignin Valorization 149
5 Innovative Lignin Streams: Preserving ?-O-4 Bonds During Fractionation 150
5.1 Mild Fractionation: Passive Approach 150
5.1.1 Ammonia 150
5.1.2 Ionic Liquids 151
5.1.3 Flow-Through Reactor Setups for Acid Hydrolysis 152
5.1.4 ?-Valerolactone 152
5.1.5 Mechanical Pretreatment 153
5.2 Chemical Stabilization During Fractionation: Active Approach 153
6 Depolymerization of Native Lignin to Stable Monomers 155
6.1 Reductive Catalytic Fractionation (RCF) 155
6.2 Reductive One-Pot Processing 157
6.3 Oxidative Catalytic Fractionation (OCF) 158
6.4 Other Opportunities Towards Higher Lignin Monomer Yields from Native Lignin 159
6.4.1 Thermal (Fast-Pyrolysis) 159
6.4.2 Solvolytic 159
6.4.3 Base-Catalyzed 160
6.4.4 Acid-Catalyzed 160
7 Perspective on Lignin-Derived Chemicals 161
7.1 Direct Utilization 161
7.2 Chemocatalytic Upgrading 162
7.3 Biocatalytic Upgrading 163
8 Conclusions 164
Acknowledgements 165
References 165
Lignin Depolymerization to BTXs 173
Abstract 173
1 Introduction 173
2 State of the Art 175
3 Plant Lignin Structure 177
4 Extraction and Isolation of Lignin. Repolymerization Phenomenon 177
5 Strategies for Lignin Conversion 179
5.1 Basic and Acid-Catalyzed Depolymerization 180
5.2 Oxidative Depolymerization 183
5.3 Ionic-Liquid Catalyzed Depolymerization 183
6 Heterogeneous Catalysis Depolymerization 184
6.1 Deoxygenation from Lignin (One step) 185
6.2 Deoxygenation from Bio-oil or Target Oxygenated Compounds (two steps) 188
7 Enzymatic Depolymerization 191
8 Future Perspectives 194
Acknowledgements 196
References 197
Heterogeneous Catalyzed Thermochemical Conversion of Lignin Model Compounds: An Overview 201
Abstract 201
1 Introduction 202
1.1 Biomass Pretreatment 204
1.1.1 Kraft Lignin 204
1.1.2 Alkali-Pulping Lignin 204
1.1.3 Sulfite Process Lignin 204
1.1.4 Steam Explosion 205
1.1.5 Organosolv Lignin 205
1.1.6 Acid-Hydrolysis Lignin 205
1.1.7 Enzymatic-Hydrolysis Lignin 206
1.2 Lignin Thermochemical Conversion 206
1.3 Lignin Model Compounds 207
1.4 Heterogeneous Catalysis 209
1.5 Overview and General Considerations for This Review 209
2 Reductive Conversion Processes 210
2.1 Hydroprocessing of Lignin Model Compounds 210
2.1.1 Monomers 210
2.1.2 Dimers 220
2.2 Catalytic Transfer Hydrogenation of Lignin Model Compounds 226
2.2.1 Monomers 226
2.2.2 Dimers 231
3 Oxidative Conversion Processes 234
3.1 Monomers 235
3.2 Dimers 244
4 Pyrolytic Processes 244
4.1 Monomers 247
4.2 Dimers 248
4.3 Reforming of Lignin Pyrolysis Oil Model Compounds 249
5 Hydrolytic Processes 259
6 Overview and Future Perspectives 261
References 265

Produkt-Details

• Erscheint lt. Verlag: 25.3.2020
• Reihe/Serie: Topics in Current Chemistry Collections
• Reihe/Serie: Topics in Current Chemistry Collections
• Zusatzinfo: VI, 271 p. 74 illus., 43 illus. in color.
• Sprache: englisch
• Themenwelt: Naturwissenschaften ► Chemie ► Organische Chemie
• Themenwelt: Wirtschaft
• Schlagworte: aromatic structure • lignin structure • Lignosulfonates • macro monomers and polymers applications • Platform chemicals
• ISBN-10: 3-030-00590-9 / 3030005909
• ISBN-13: 978-3-030-00590-0 / 9783030005900