Chapter
Part I Drop-in Bio-Based Chemicals
Chapter 1 Olefins from Biomass
1.2 Olefins from Bioalcohols
1.2.1 Ethanol to Ethylene
1.2.2 Ethanol to Butadiene
1.2.3 C3 Alcohols to Olefins
1.2.4 C4 Alcohols to Olefins
1.3 Alternative Routes to Bio-Olefins
Chapter 2 Aromatics from Biomasses: Technological Options for Chemocatalytic Transformations
2.1 The Synthesis of Bioaromatics
2.2 The Synthesis of Bio-p-Xylene, a Precursor for Bioterephthalic Acid
2.2.1 Aromatic Hydrocarbons from Sugars
2.2.1.1 The Virent Technology
2.2.2 Aromatic Hydrocarbons from Lignocellulose or Other Biomass
2.2.2.1 The Anellotech Technology
2.2.3 p-Xylene from Bioalcohols
2.2.3.1 The Gevo Technology
2.2.3.2 p-Xylene from Bioethanol
2.2.4 Aromatic Hydrocarbons from Lignin
2.2.4.1 The Biochemtex MOGHI Process
2.3 The Synthesis of Bioterephthalic Acid without the Intermediate Formation of p-Xylene
2.4 Technoeconomic and Environmental Assessment of Bio-p-Xylene Production
Chapter 3 Isostearic Acid: A Unique Fatty Acid with Great Potential
3.2 Biorefinery and Related Concepts
3.3 Sustainability of Oils and Fats for Industrial Applications
3.5 Polymerization of Fatty Acids
3.5.1 Thermal Polymerization
3.5.2 Clay-Catalyzed Polymerization
3.7 Other Branched Chain Fatty Acids
3.8.1 Thermal and Oxidative Stability
3.8.2 Low-Temperature Liquidity
3.9.2 Cosmetics and Personal Care
3.10 Selective Routes for the Production of ISAC
3.10.1 Optimization of the clay-catalyzed process
3.10.2 Zeolite-catalyzed branching in the petroleum industry
3.10.3 Zeolite-catalyzed branching of fatty acids
3.10.4 Ferrierite-a breakthrough in fatty acid isomerization
3.11 Summary and Conclusions
Chapter 4 Biosyngas and Derived Products from Gasification and Aqueous Phase Reforming
4.2.1 Gasification Process
4.2.1.1 Densification and High-Temperature Gasification
4.2.1.2 Direct Gasification
4.2.2 Catalytic Gasification
4.2.3 Gas Upgrading by Reforming
4.2.4 Downstream of the Reformer
4.2.5 Future Process Breakthrough
4.3 Aqueous Phase Reforming
4.3.1 Thermodynamic and Kinetic Considerations
4.3.2 Catalysts for APR Reaction
4.3.3 Reaction Conditions and Feed
4.3.4 Mechanism of Reaction
4.3.5 APR on Biomass Fractions
4.3.6 Pilot Plants and Patents
4.3.7 Integration of the APR Process in a Biorefinery
Chapter 5 The Hydrogenation of Vegetable Oil to Jet and Diesel Fuels in a Complex Refining Scenario
5.2.2 Animal Oils and Fats
5.2.3 Triglycerides from Algae
5.3 Hydroconversion Processes of Vegetable Oils and Animal Fats
5.3.1 EcofiningTM Process
5.3.2 Product Characteristics and Fuel Specification
5.4 Chemistry of Triglycerides Hydroconversion
5.4.1 Deoxygenation over Sulfided Catalysts
5.5 Life Cycle Assessment and Emission
5.6 The Green Refinery Project
Chapter 6 Synthesis of Adipic Acid Starting from Renewable Raw Materials
6.2 Challenges for Bio-Based Chemicals Production
6.3 Choice of Adipic Acid as Product Target by Rennovia
6.4 Conventional and Fermentation-Based Adipic Acid Production Technologies
6.5 Rennovia's Bio-Based Adipic Acid Production Technology
6.6 Step 1: Selective Oxidation of Glucose to Glucaric Acid
6.6.1 Identification of Selective Catalysts for Aerobic Oxidation of Glucose to Glucaric Acid at Native pH
6.6.2 Demonstration of Long-Term Catalyst Stability for Glucose Oxidation Reaction
6.7 Step 2: Selective Hydrodeoxygenation of Glucaric Acid to Adipic Acid
6.7.1 Identification of Catalysts and Conditions for the Selective Reduction of Glucaric Acid to Adipic Acid
6.7.2 Reaction Pathways for the Selective Reduction of Glucaric Acid to Adipic Acid
6.7.3 Demonstration of Long-Term Catalyst Stability for Glucaric Acid Hydrodeoxygenation Reaction
6.8 Current Status of Rennovia's Bio-Based Adipic Acid Process Technology
6.9 Bio- versus Petro-Based Adipic Acid Production Economics
6.10 Life Cycle Assessment
Chapter 7 Industrial Production of Succinic Acid
7.2 Market and Applications
7.2.1 Hydrogenation of Succinic Acid
7.2.2 Polyester-Polyurethane Markets
7.3.1 Biochemical Pathway and Host Microorganism Considerations
7.3.2 Fermentation Process Options
7.3.2.2 Corynebacterium glutamicum Systems
7.3.2.3 Other Bacterial Systems
7.3.2.5 Media and pH Control
7.3.2.6 Aeration and Gas Systems
7.3.3 Downstream Process Options
Chapter 8 2,5-Furandicarboxylic Acid Synthesis and Use
8.1.1 2,5-Furandicarboxylic Acid and Terephthalic Acid
8.2 Synthesis of 2,5-Furandicarboxylic Acid by Oxidation of HMF
8.2.1 Aqueous Phase Oxidation of HMF
8.2.2 Oxidation of HMF in Acetic Acid
8.2.3 Oxidative Esterification of HMF to 2,5-Furan Dimethylcarboxylate (FDMC)
8.3 Synthesis of 2,5-Furandicarboxylic Acid from Carbohydrates and Furfural
8.4 2,5-Furandicarboxylic Acid-Derived Surfactants and Plasticizers
8.5 2,5-Furandicarboxylic Acid-Derived Polymers
8.5.1 Synthesis and Properties of Polyethylene Furandicarboxylate (PEF) and Related Polyesters
8.5.2 Synthesis and Properties of Other Furanic Polyesters and Copolyesters
Chapter 9 Production of Bioacrylic Acid
9.2.1 Production of AA from GLY
9.2.1.1 Direct Pathway from GLY to AA
9.2.1.2 Indirect Pathways from GLY to AA
9.2.2 Production of AA from LA
9.2.2.2 Direct Dehydration of LA to AA
9.2.3 Production of AA from Biopropylene
9.4 Summary and Conclusions
Chapter 10 Production of Ethylene and Propylene Glycol from Lignocellulose
10.2.1 Possible Transformation Schemes
10.2.2 Undesired Side Reactions
10.2.3 C-C and C-O Bond Cleavage for Selective Glycol Formation
10.3.1 Ruthenium Catalysts
10.3.1.1 C5 and C6 Sugar Alcohols and Monosaccharides
10.3.2 Platinum Catalysts
10.3.2.1 C5 and C6 Sugar Alcohols and Monosaccharides
10.3.3 Other Noble Metal Catalysts
10.3.4 Nickel-Based Catalysts
10.3.4.1 C5 and C6 Monosaccharides and Sugar Alcohols
10.3.5 Copper and Other Base Metal Catalysts
10.3.5.1 C5 and C6 Monosaccharides and Sugar Alcohols
10.4 Direct Formation of Glycols from Lignocellulose
10.5 Technical Application of Glycol Production
10.6 Summary and Conclusion
Part III Polymers from Bio-Based building blocks
Chapter 12 Polymers from Pristine and Modified Natural Monomers
12.1 Monomers and Polymers from Vegetable Oils
12.2 Sugar-Derived Monomers and Polymers
12.2.2 Polymers from 1,4:3,6-Dianhydrohexitols
12.2.3 Polymers from Diacetals Derived from Sugars
12.3 Polymers from Terpenes and Rosin
12.3.2 Terpenes and Rosin Production and Application
12.3.2.1 Isomerization Reactions to Obtain Different Terpenes
12.3.3 Terpenes as Monomers for Polymer Synthesis without Any Modification
12.3.3.1 Cationic Polymerization of Pinenes
12.3.4 Terpenes as Monomers after Chemical Modification
12.3.4.1 Limonene Modified by the Thiol-Ene Reaction
12.3.4.2 Dimethylstyrene from Limonene
12.3.4.3 Terephthalic Acid Synthesis from Terpenes
12.3.4.4 Epoxidation of Limonene for the Synthesis of Polycarbonates and Polyurethanes
12.3.4.5 Copolymers Containing Terpenes
12.3.7.1 Thermoset Polymers from Rosin
12.3.7.2 Thermoplastic Polymers from Rosin
12.4 Final Considerations
Chapter 13 Polymers from Monomers Derived from Biomass
13.1 Polymers Derived from Furans
13.1.5 Polymers Based on the DA Reaction
13.2 Polymers from Diacids, Hydroxyacids, Diols
13.2.2 SA and Its Polymers
13.2.2.2 Poly(ester amide)s
13.2.3 Adipic Acid and Its Polymers
13.2.4 Levulinic Acid and Its Polymers
13.2.5 Vanillin, Vanillic, and Ferulic Acids and Derived Polymers
13.2.6 Diols and Their Polymers
13.3.2 Linear 1,3-Linked Glycerol Polymers
13.4 Final Considerations
Part IV Reactions Applied to Biomass Valorization
Chapter 14 Beyond H2: Exploiting H-Transfer Reaction as a Tool for the Catalytic Reduction of Biomass
14.2 MPV Reaction Using Homogeneous Catalysts
14.3 MPV Reaction Using Heterogeneous Catalysts
14.3.1 Mechanism and Path on Heterogeneous Catalysts
14.4 H-Transfer Reaction on Molecules Derived from Biomass
14.4.1 Levulinic Acid Hydrogenation
14.4.2 Furan Derivative Hydrogenation
14.4.3 Lignin and Sugar Hydrogenation
14.4.4 Glycerol Dehydration/Hydrogenation
14.5 Industrial Applications of the MPV Reaction
Chapter 15 Selective Oxidation of Biomass Constitutive Polymers to Valuable Platform Molecules and Chemicals
15.2 Selective Oxidation of Cellulose
15.2.1 Platform Molecules Obtained via Selective Oxidation of Cellulose
15.2.1.2 Gluconic and Glycolic Acids
15.3 Selective Oxidation of Lignin
15.3.1 Selective Oxidation of Lignin in the Presence of Homogenous Catalysts
15.3.2 Selective Oxidation of Lignin in the Presence of Heterogeneous Catalysts
15.4 Selective Oxidation of Starch
Chapter 16 Deoxygenation of Liquid and Liquefied Biomass
16.2 General Remarks on Deoxygenation
16.3 Deoxygenation of Model Compounds
16.3.1 Phenol and Alkylphenols
16.3.2 Guaiacol and Substituted Guaiacols
16.3.3 Lignin-Derived Molecules
16.3.4 Short-Chain Carboxylic Acids
16.3.5 Furans, Furfurals, and Benzofurans
16.4 Deoxygenation of Liquid and Liquefied Biomass
16.4.2 Bio-Oils from Hydrothermal Liquefaction or Fast Pyrolysis
16.5 Deoxygenation in Absence of Hydrogen
16.5.3 Long-Chain Carboxylic Acids
16.5.4 Biomass and Liquefied Biomass Deoxygenation by Hydrothermal Processes
16.5.4.2 Hydrothermal Upgrading
16.5.4.3 Supercritical Water Processing
16.6 Conclusions and Outlook
Chapter 17 C-C Coupling for Biomass-Derived Furanics Upgrading to Chemicals and Fuels
17.2 Upgrading Strategy for Furanics
17.2.1 Aldol Condensation of Furfural-HMF
17.2.1.1 Mechanism of Aldol Condensation Reaction
17.2.1.2 Catalysts for Aldol Condensation
17.2.1.3 Upgrading Strategy
17.2.2 Hydroxyalkylation-Alkylation: Sylvan Process
17.2.2.1 Mechanism of Hydroxyalkylation-Alkylation (HAA)
17.2.2.2 Catalysts for Hydroxyalkylation-Alkylation (HAA)
17.2.2.3 Upgrading Strategy
17.2.3.1 Mechanism of Diels-Alder Reaction
17.2.3.2 Catalysts for Diels-Alder Reaction
17.2.3.3 Upgrading Strategy
17.2.4 Piancatelli Reaction-Ring Rearrangement of Furfural
17.2.4.1 Mechanism of Furfural Ring Rearrangement
17.2.4.2 Catalysts for Ring Rearrangement of Furfural
17.2.4.3 Upgrading Strategy
17.2.5 Oxidation of Furanics
17.2.5.1 Mechanism of Furanics Oxidation
17.2.5.2 Catalysts for Furfural Oxidation
17.2.5.3 Upgrading Strategy
17.2.6 Dimerization of Furfural via Oxidative Coupling
17.3 Summary and Conclusion
Part V Biorefineries and Value Chains
Chapter 18 A Vision for Future Biorefineries
18.2 The Concept of Biorefinery
18.3 The Changing Model of Biorefinery
18.3.1 Olefin Biorefinery
18.3.2 Biorefinery for Flexible Production of Chemicals and Fuels
18.4 Integrate CO2 Use and Solar Energy within Biorefineries
Chapter 19 Oleochemical Biorefinery
19.1 Oleochemistry Overview
19.1.2 Value Chain for Oleochemistry
19.1.2.3 Oleochemical Substances
19.2 Applications and Markets for Selected Oleochemical Products
19.2.1 Applications for Products from Oleochemistry Value Chain
19.2.2 Fats and Oil as Raw Materials for Oleochemicals
19.2.3 Fatty Acid Market: History, Present, and Prognosis
19.2.4 Glycerine Market: History, Present, and Prognosis
19.3 Future Perspectives of Oleochemistry in the View of Bioeconomy
19.3.1 Potentials for Oleochemistry
19.3.2 Legal and Regulatory Background
Chapter 20 Arkema's Integrated Plant-Based Factories
20.2 Arkema's Plant-Based Factories
20.2.1 Marseille Saint-Menet (France)
20.2.3 Blooming Prairie (United States)
20.3 Cross-Metathesis of Vegetable Oil Plant
20.3.1 From Rapeseed Oil to a Synthetic Palm Kernel or Coconut Oil
20.3.2 Preliminary Economic Analysis
20.3.4 Lessons for Research and Development Program
20.3.5 Lessons for Legislators
20.4 Summary and Conclusions
Chapter 21 Colocation as Model for Production of Bio-Based Chemicals from Starch
21.2 Wet Milling of Cereal Grains: At the Heart of the Starch Biorefinery
21.2.1 Wet Milling of Maize (Corn)
21.2.2 Wet Milling of Wheat
21.2.3 Downstream Processing of Starch Slurry
21.2.4 Cereal Grain Wet Mill Products as Raw Materials for Bio-Based Chemicals
21.3 The Model of Colocation
21.3.1 Creating Value through Economies of Scale
21.3.2 The Benefits Gained from Colocation at Starch Biorefineries
21.3.2.1 Increased Cash Flow
21.3.2.2 Reduced Capital Demand
21.3.2.3 Reduced Manufacturing Risk
21.4 Examples of Starch-Based Chemicals Produced in a Colocation Model
21.4.1.1 Corn Wet Mills for Biofuel Ethanol
21.4.1.2 Wheat Wet Mill for Premium Grain Alcohol
21.4.5 2-Keto-L-gulonic Acid
21.5 Summary and Conclusions
Chapter 22 Technologies, Products, and Economic Viability of a Sugarcane Biorefinery in Brazil
22.2 Biorefineries: Building the Basis of a New Chemical Industry
22.2.1 Biomasses/Residues and Their Costs
22.2.2 Competing Technologies/Products in Development: The Importance of Biotechnology
22.3 Sugarcane-Based Biorefineries in Brazil: Status
22.3.1 An Industry with a History of Evolution
22.3.2 Existing Biorefineries in Brazil
22.3.2.1 Bioethylene and Biopolyethylene
22.3.2.3 Other Biorefineries
22.4 A Method for Technical Economic Evaluation
22.4.1 Braskem's Roadmap for Chemicals from RRMs
22.4.2 Braskem's Method for the Evaluating the Chemicals Produced from RRMs
22.5 The Sugarcane Biorefinery of the Future: Model Comparison
22.5.1 Conventional Sugarcane Ethanol Plant
22.5.2 Stand-Alone Cellulosic Ethanol Plant
22.5.3 Integrated Conventional and Cellulosic Ethanol Factory
22.5.4 Biorefinery Producing Ethanol, Raw Sugar, and Succinic Acid
22.5.5 Biorefinery Producing Ethanol, Raw Sugar, Succinic Acid, and Butanol
Chapter 23 Integrated Biorefinery to Renewable-Based Chemicals
23.2 An Alternative Source of Natural Rubber: Toward a Guayule-Based Biorefinery
23.3 Toward Renewable Butadiene
Chapter 24 Chemistry and Chemicals from Renewables Resources within Solvay
24.2 Chemistry from Triglycerides
24.2.2 AugeoTM Family: Glycerol as a Platform for Green Solvents
24.2.3.2 Polymer Intrinsic Properties
24.2.3.3 Main Technological Properties and Applications
24.2.4 A New Generation of "Sustainable" Viscoelastic Surfactants Based on Renewable Oleochemicals
24.2.4.2 Micellar Structure and Rheology
24.2.4.3 VES Fluids in the Recovery of Oil and Gas
24.2.4.4 Other Novel Applications for VES
24.3 Chemistry on Cellulose: Cellulose Acetate
24.3.1 What Is Cellulose Acetate?
24.3.2 An History That Started More Than 100,Years Ago
24.3.3 Main Markets and Applications for CA
24.3.3.3 Plastic Applications
24.3.4 Cellulose Acetate Today and Tomorrow
24.4.1.2 Why Is Guar Unique?
24.4.2 Nonderivatized Guar: From Physicochemical Properties to Major Applications
24.4.3 Guar Derivatives: From Physicochemical Properties to Major Applications
24.4.4 Challenges and Opportunities
24.6 Summary and Conclusions
Chapter 25 Biomass Transformation by Thermo- and Biochemical Processes to Diesel Fuel Intermediates
25.2 Biological Processes
25.2.2.1 Photoautotrophic Cultivation Technology
25.2.2.2 Heterotrophic Cultivation Technology
25.2.3 Microbial and Algal Oils Upgrading to Fuels
25.3.2 Hydrothermal Liquefaction
Chapter 26 Food Supply Chain Waste: Emerging Opportunities
26.2 Pretreatment and Extraction
26.3.1 Food Additives and Functional Foods
26.3.3 Platform Chemicals and Biopolymers
26.4.1 Combining Chemical and Bioprocessing
26.4.2 Chemical Processing and the Biorefinery
26.5 Technical and Sustainability Assessment and Policy Analysis
26.5.1 Assessing a Market
26.5.2 Cost Analysis of Biorefining
26.5.3 Sustainability Transition Patterns
26.6 Conclusions and Outlook
Chemicals and Fuels from Bio-Based Building Blocks
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