Publication YXY 2013

R-J. van Putten, J.C. van der Waal, E. de Jong, C.B. Rasrendra, H.J. Heeres, J.G. de Vries, Chem. Rev. 2013, 113, 1499.

1. Introduction 2. Nutritional and Toxicological Aspects of HMF and Its Derivatives2.1. HMF Occurrence in Our Diet 2.2. Metabolic Breakdown of HMF and Its Derivatives 2.3. Toxicological Effects of HMF and Its Derivatives 3. Dehydration Chemistry3.1. Neutral Monomeric Sugars3.1.1. Mechanistic Aspects 3.1.2. Byproducts 3.1.3. Computational Studies 3.2. Disaccharides and Polysaccharides 3.3. Sugar Acids 3.4. Conclusion 4. Process Chemistry4.1. HMF Formation in Single-Phase Systems4.1.1. Fructose Dehydration in Single-Phase Systems 4.1.2. Glucose Dehydration in Single-Phase Systems 4.1.3. Dehydration of Disaccharides, Trisaccharides, and Polysaccharides and Biomass Feedstock in Single-Phase Systems 4.2. HMF Formation in Biphasic Solvent Systems4.2.1. Fructose Dehydration in Biphasic Solvent Systems 4.2.2. Glucose Dehydration in Biphasic Solvent Systems 4.2.3. Dehydration of Oligo- and Polysaccharides in Biphasic Solvent Systems 4.3. HMF Formation in Ionic Liquids4.3.1. Definition of Ionic Liquids 4.3.2. Dehydration of Carbohydrates to HMF in Ionic Liquids 4.3.3. Conclusion on HMF Production in Ionic Liquids 5. Process Technology5.1. Introduction5.1.1. Aqueous Reaction Systems 5.1.2. Nonaqueous Reaction Systems 5.1.3. Mixed Solvent Reaction Systems 5.2. Kinetic Studies on HMF Formation5.2.1. Kinetic Studies on the Formation of HMF from Fructose 5.2.2. Kinetic Studies on the Formation HMF from Glucose 5.2.3. Kinetic Studies on the Formation of HMF from Cellulose, Lignocellulosic Biomass, and Fructan-Based Biomass 5.2.4. Kinetic Studies on the Decomposition of HMF 5.3. Reactor Concepts5.3.1. Reactions in Water 5.3.2. Reactions in Nonaqueous and Mixed Solvent Systems 5.4. Separation and Purification Strategies5.4.1. Separation and Purification Strategies for Aqueous Systems 5.4.2. Separation and Purification Strategies for Nonaqueous Systems 5.5. Pilot Scale Production of HMF5.5.1. Pilot Scale Studies of Aqueous HMF Processes 5.5.2. Pilot Scale Production Using Nonaqueous Solvents 5.5.3. Pilot Scale Production Using Mixed Solvent Systems 5.5.4. Pilot Scale Production of HMF Involving an HMF Derivative 5.6. Technoeconomic Evaluations of Different Modes of HMF Production 6. Relevance of 5-Hydroxymethylfurfural as a Platform Chemical6.1. Conversion of HMF to Monomers for Polymers6.1.1. HMF-Based Diols 6.1.2. 2,5-Diformylfuran 6.1.3. 2,5-Furandicarboxylic Acid (FDCA), Adipic Acid, and 5-Hydroxymethyl-2-furan Carboxylic Acid 6.1.4. Conversion of HMF into Other Monomers 6.2. Fine Chemicals6.2.1. Pharmaceuticals 6.2.2. Agrochemicals 6.2.3. Flavors and Fragrances 6.2.4. Natural Products 6.2.5. Macrocycles 6.2.6. Heterocycles 6.2.7. Sugar Derivatives 6.2.8. Spiroketals 6.2.9. Other Synthetic Conversions 6.3. HMF as Precursor of Fuel Components 7. Conclusions

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