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White Biotechnology for Sustainable Chemistry

BOOK

White Biotechnology for Sustainable Chemistry

Maria Alice Coelho | Bernardo D Ribeiro

(2015)

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Book Details

ISBN
978-1-78262-408-0
Edition
1
Language
English
Pages
434
Subjects
Environmental chemistry
Catalysis
Biotechnology
Industrial chemistry & chemical engineering
Environmental science, engineering & technology

Abstract

White biotechnology is the use of enzymes and microorganisms in industrial production through applied biocatalysis. This allows for milder reaction conditions (pH and temperature) and the use of more environmentally-compatible catalysts and solvents. This, in turn, leads to processes which are shorter, generate less waste, making them both environmentally and economically more attractive than conventional routes.

This book describes the use of white biotechnology within the sustainable chemistry concept, covering waste minimization; the use of alternative solvents (supercritical fluids, pressurized gases, ionic liquids and micellar systems) and energies (microwaves and ultrasound); sustainable approaches for the production of fine and bulk chemicals (aromas, polymers, pharmaceuticals and enzymes); the use of renewable resources and agro-industrial residues; and biocatalysts recycling.

Covering industrial processes and new technologies, this book combines expertise from academia and industry. It is a valuable resource for researchers and industrialists working in biotechnology, green chemistry and sustainability.


Maria Alice Z Coelho is a Professor at the Federal University of Rio de Janeiro, Brazil, and is responsible for the Biosystems Engineering Group. Her research focusses on bioprocess engineering.
 
Bernardo D Ribeiro is a Professor at the Federal University of Rio de Janeiro, Brazil, where he researches clean technologies with a sustainable approach.

Table of Contents

Section Title Page Action Price
Cover Cover
White Biotechnology for Sustainable Chemistry i
Preface vii
Contents ix
Chapter 1 - Principles of Green Chemistry and White Biotechnology 1
1.1 Green Chemistry: Could Chemistry be Greener 1
1.2 White Biotechnology 2
1.3 Concluding Remarks 5
References 7
Chapter 2 - Sustainability, Green Chemistry and White Biotechnology 9
2.1 Introduction to Green Chemistry and Sustainability 9
2.2 Green Chemistry Metrics 13
2.3 Environmental Impact and Sustainability Metrics 16
2.4 The Role of Catalysis in Waste Minimisation 18
2.5 Solvents and Multiphase Catalysis 19
2.6 Green Chemistry and White Biotechnology 21
2.7 Green and Sustainability Metrics of White Biotechnology 22
2.7.1 Fermentation processes 22
2.7.2 Enzymatic Production of an Atorvastatin Intermediate 22
2.7.3 Enzymatic Synthesis of Sitagliptin 26
2.7.4 Enzymatic Production of Myristyl Myristate 28
2.8 White Biotechnology, Green Chemistry and the Utilisation of Waste Biomass 29
2.9 Conclusions & Future Prospects 32
References 32
Chapter 3 - Biocatalysis in Organic Media 36
3.1 Enzyme Structure and Function 36
3.2 Enzymes and Biocatalysts 37
3.3 Enzyme Catalysis in Aqueous Media 38
3.4 Enzyme Biocatalysis in Non-Aqueous (Non-Conventional) Media 40
3.4.1 Gases 41
3.4.2 Supercritical Fluids 41
3.4.3 Ionic Liquids 41
3.4.4 Semisolid Systems 42
3.4.5 Reactions Conducted at Very High Substrate Concentration 42
3.5 Enzyme Biocatalysis in Organic Solvents 42
3.6 Enzymes as Catalysts for Organic Synthesis 45
3.7 Conclusions 46
References 47
Chapter 4 - Microwave Assisted Enzyme Catalysis: Practice and Perspective 52
4.1 Introduction 52
4.2 Enzyme Catalysis 54
4.3 Microwave Irradiation 55
4.3.1 Brief History of Microwave Technology 56
4.3.2 Microwave Principles 57
4.3.2.1 Dipole Polarization 57
4.3.2.2 Ionic Conduction 58
4.3.3 Interaction Between Microwave Irradiation and Reaction Medium 58
4.3.4 Microwave Heating vs. Conventional Heating 60
4.3.5 Application of Microwaves in Enzymatic Reactions – Green Chemistry Approach 61
4.3.5.1 Initial Studies on the Application of Microwave Irradiation to Enzymatic Reactions 62
4.4 Application to Different Industrially Relevant Reactions 65
4.4.1 Microwave Assisted Enzymatic Hydrolysis for Proteomics 66
4.4.2 Application of Microwave Irradiation for Enzyme Catalyzed Biodiesel Production 73
4.4.3 Application of Microwave Irradiation to Enzyme Catalyzed Polymer Synthesis 74
4.4.4 Application of Microwave Irradiation for Enzyme Catalyzed Reactions in the Chemical Industry 75
4.4.5 Application of Microwaves for Enzyme Catalyzed Reactions in the Food and Cosmetics Industries 77
4.4.6 Application of Microwave Heating for Enzyme Catalyzed Reactions in the Pharmaceutical Industry 80
4.4.7 Separation of Racemic Compounds 83
4.4.8 Application of Microwaves to Enzyme Immobilization 89
4.5 Kinetic Models and Their Critical Analysis 91
4.6 Conclusions 96
Nomenclature 97
References 98
Chapter 5 - Lipase-Catalyzed Reactions in Pressurized Fluids 104
5.1 Introduction 104
5.2 Behavior of Lipases in Supercritical and Compressed Fluids 106
5.2.1 Effect of Nature of Solvent 108
5.2.2 Effects of Changing Pressure 114
5.2.3 Effects of Changing Temperature 116
5.2.4 Effect of Changing Water Content 118
5.2.5 Water Activity (aw) 120
5.2.6 Effect of Pressurization and Depressurization 121
5.3 Lipase-Catalyzed Reactions in Supercritical and Compressed Fluids 121
5.3.1 Esterification 122
5.3.2 Transesterification 128
5.3.3 Interesterification 129
5.3.4 Hydrolysis 130
5.4 Conclusions 131
References 131
Chapter 6 - Biocatalysis in Ionic Liquids 136
6.1 Ionic Liquids 136
6.2 Enzymes in Ionic Liquids 139
6.2.1 Lipases, Proteases and Esterases 143
6.2.2 Glycosidases 150
6.2.3 Other Enzymes 150
6.3 Whole-Cell Processes in Ionic Liquids 154
6.3.1 Toxicity Toward Microorganisms 154
6.3.1.1 Methods 155
6.3.1.2 General Trends 156
6.3.2 Whole-Cell Biocatalysis 160
References 168
Chapter 7 - Biocatalysis in Micellar Systems 178
7.1 Introduction 178
7.1.1 Biocatalysis 178
7.1.2 Micellar Systems 179
7.2 Oil-in-Water Systems 180
7.2.1 Emulsion Characterization 181
7.2.2 Enzyme Catalysis 184
7.2.2.1 Oil and Alkane Systems 184
7.2.2.2 Other Solvents 185
7.2.3 Whole-Cell Biotransformations 185
7.3 Water-in-Oil Systems 187
7.3.1 Influence of Phase Composition 188
7.3.1.1 Solvents 188
7.3.1.2 Amphiphiles 189
7.3.1.3 Aqueous Phase 189
7.3.2 Enzymatic Reactions 191
7.3.3 Immobilization of Reverse Micelles 192
7.4 Concluding Remarks 192
References 193
Chapter 8 - Green Downstream Processing in the Production of Enzymes 197
8.1 Introduction 197
8.2 Initial Separation Steps for Enzyme Recovery 198
8.3 Concentration Steps in Enzyme Downstream Processing 199
8.3.1 Precipitation 199
8.3.2 Membrane Separation 200
8.3.2.1 Ultrafiltration 200
8.4 Purification Technologies for Enzymes 201
8.4.1 Chromatography 201
8.4.2 Biphasic Systems 203
8.4.2.1 Extractive Bioconversion 203
8.5 Conclusions 204
Acknowledgements 204
References 204
Chapter 9 - Lipases in Enantioselective Syntheses: Evolution of Technology and Recent Applications 207
9.1 Introduction 207
9.2 Lipase-Catalyzed Enantioselective Syntheses 208
9.2.1 Classical Kinetic Resolution 210
9.2.2 Deracemization Processes 211
9.2.2.1 Cyclic (Stepwise) Deracemization 211
9.2.2.2 Enantioconvergent Processes (ECPs) 213
9.2.2.3 Dynamic Kinetic Resolution (DKR) 214
9.2.2.3.1 DKR via Enzymatic Racemization.Biocatalyzed racemization is regarded as an attractive option in DKR, since it is performed under... 214
9.2.2.3.2 DKR via Chemical Racemization by Deprotonation–Protonation.If the stereocenter in the racemic material is attached to an acidic ... 214
9.2.2.3.3 DKR via Chemical Racemization by Addition–Elimination.Cyanohydrins, hemiacetals, hemiaminals and hemithioacetals may engage in s... 214
9.2.2.3.4 DKR via Nucleophilic Substitution.DKRs of α-haloesters via racemization by substitution with halides are known.33,34 In these ca... 214
9.2.2.3.5 DKR via Metal Catalysis.A variety of metal catalysts for the racemization step have been reported (Table 9.3), but only a few co... 215
9.2.3 Enantioselective Desymmetrizations 218
9.3 Medium Engineering 219
9.4 Immobilization of Lipases 224
9.4.1 Brief Background 224
9.4.2 Immobilization Protocols 224
9.4.2.1 Physical Adsorption 225
9.4.2.2 Covalent Attachment 227
9.5 Tailor-Made Lipases: Improving the Enantioselectivity 228
9.6 Reactor Configuration 230
9.7 The Use of Ionic Liquids 232
References 236
Chapter 10 - Redox Biotechnological Processes Applied to Fine Chemicals 245
10.1 Introduction 245
10.2 Redox Enzymes 246
10.3 Oxidation Reactions 247
10.3.1 Hydroxylation 247
10.3.1.1 Benzylic Moiety 248
10.3.1.2 Allylic Moiety 248
10.3.2 Epoxidation 249
10.3.3 Baeyer–Villiger Oxidation 250
10.3.4 Sulfide Oxidation 252
10.3.5 Lipase-Mediated Oxidation 254
10.4 Reduction Reactions 257
10.4.1 Reduction of Diketones 257
10.4.2 Reduction of α-Methyleneketones 261
10.4.3 Reduction of α-Haloketones and α-Haloenones 263
10.5 Conclusions 267
Acknowledgements 268
References 268
Chapter 11 - Production of Polymers by White Biotechnology 274
11.1 Introduction – Production of Polymers via Conventional Chemical Processes 274
11.2 Monomer Production by White Biotechnology 277
11.2.1 Microbial Production of Monomers 277
11.2.1.1 Ethylene 277
11.2.1.2 Propylene 277
11.2.1.3 Isoprene 280
11.2.1.4 Diols 280
11.2.1.5 Diamines 280
11.2.1.6 Dicarboxylic Acid 280
11.2.1.7 Hydroxycarboxylic Acid 280
11.2.2 Monomer Synthesis by Enzymatic Degradation of Naturally Occurring Polymers 281
11.2.2.1 Oligosaccharides 281
11.2.2.2 Lignin 281
11.2.3 Enzymatic Conversion of Vinyl Monomers 282
11.3 Polymer Production by White Biotechnology 282
11.3.1 General Aspects 282
11.3.2 Polymer Production by Microorganisms (Table 11.2) 282
11.3.2.1 Polyhydroxyalkanoates (PHAs) 282
11.3.2.2 Poly(lactic acid) (PLA) 284
11.3.2.3 Polyamides 285
11.3.2.4 Bacterial Cellulose 285
11.3.2.5 Hyaluronan (Hyaluronic Acid, HA) 285
11.3.2.6 Alginates 285
11.3.3 Polymer Production via Biosynthetic Pathways In vitro 286
11.3.4 Enzymatic Polymerization 286
11.3.4.1 Polyester Synthesis Catalyzed by Enzymes (Table 11.3) 286
11.3.4.1.1 Condensation Polymerization by Lipase89–97.Polyesters are polymers which contain ester moieties in their main chains. Organic es... 286
11.3.4.1.2 Ring-Opening Polymerization (ROP) of Lactones by Lipase98–111.Lactones, cyclic esters, are excellent starting substrates for the... 287
11.3.4.2 Polysaccharide Synthesis Catalyzed by Enzymes 287
11.3.4.2.1 Condensation Polymerization Catalyzed by Glycosidases112–124.Glycosyl fluorides, sugar derivatives whose anomeric hydroxyl group... 287
11.3.4.2.2 Addition Polymerization of Sugar Oxazolines Catalyzed by Glycosidases125–129.In the previous section, a review was made of enzym... 291
11.3.4.2.3 Condensation Polymerization by Phosphorylases130,131.Amylose, α(1 → 4)glucan, can be synthesized by phosphorylase-catalyzed enzy... 291
11.3.4.3 Polyaromatics Synthesis Catalyzed by Enzymes 291
11.3.4.3.1 Oxidative Polymerization of Phenolic Compounds132–145.The enzymes responsible for the oxidation–reduction process in maintaining... 302
11.3.4.3.2 Oxidative Polymerization of Polyphenolic Compounds146–151.Flavonoids, such as catechin and rutin, are called “polyphenols”, and ... 302
11.3.4.3.3 Oxidative Polymerization of Aniline Derivatives152–155.Oxidative polymerization of aniline was conducted a century ago59 to give... 302
11.4 Future Prospects 303
References 303
Chapter 12 - Production of Aroma Compounds by White Biotechnology 310
12.1 Introduction 310
12.2 Methods for Producing Aroma Compounds 312
12.3 Why Use White Biotechnology to Produce Aroma Compounds 314
12.4 Examples of Aroma Compounds Produced Through White Biotechnology 316
12.4.1 Background and Overview: Processes, Advantages and Developments 316
12.4.2 Products Obtained—An Industrial Perspective 317
12.4.3 Production of Aroma Compounds in Bioreactors 319
12.5 Green Chemistry in the Production of Aroma Compounds 320
12.5.1 Alternative Solvents 321
12.5.1.1 Supercritical Fluids 321
12.5.1.2 Pressurized Liquid Extractions (PLEs) 322
12.5.1.3 Ionic Liquids (ILs) 322
12.5.2 Alternative Extraction Methods 323
12.5.2.1 Ultrasound Assisted Extraction (UAE) 323
12.5.2.2 Microwave Heating 323
12.5.3 Alternative Substrates 324
12.5.3.1 Alternative Substrates and Culture Media for Bioaroma Production 324
12.5.3.2 Rational Use of Biocatalysts 325
12.6 Concluding Remarks 326
References 327
Chapter 13 - Biotransformation Using Plant Cell Culture Systems and Tissues 333
13.1 Biotransformation and Green Chemistry 333
13.2 Plant Cell Cultures 334
13.3 Use of Plant Cell Cultures in Biotransformation 337
13.3.1 Biotransformation Using Cell Immobilization 347
13.3.2 β-Cyclodextrins in Biotransformation 349
13.4 Use of Whole or Parts of Plants in Biotransformation 349
13.4.1 Phytoremediation 352
13.4.2 Biosensors 352
13.4.3 Reduction 353
13.4.4 Hydrolysis 354
13.4.5 Oxidation 354
References 355
Chapter 14 - Development of Processes for the Production of Bulk Chemicals by Fermentation at Industrial Scale – An Integrated Approach 362
14.1 Introduction 362
14.1.1 The Potential of White Biotechnology for the Production of Bulk Chemicals 362
14.1.2 Setup of a Development Project 363
14.2 Steering the Direction of the Development Project 364
14.2.1 The Three Typical Main Business Drivers in Large Scale Bioproduction 364
14.2.1.1 Reduce Cost of Production 365
14.2.1.2 Reduce CO2 Emissions 365
14.2.1.3 Become Independent of Fossil Resources 365
14.2.2 The Three Typical Main Parameters for Reducing the Cost of Production 365
14.2.2.1 Product Yield 365
14.2.2.2 Productivity (Space–Time Yield) 366
14.2.2.3 Product Concentration in the Fermenter 366
14.2.3 Alignment with Business Drivers 366
14.3 Strain Development 368
14.3.1 Search for Natural Producers 368
14.3.2 Metagenomics 368
14.3.3 Host Strain Selection 368
14.3.4 Random Mutagenesis 369
14.3.5 Screening 370
14.3.6 Metabolic Engineering 371
14.3.6.1 Analysis: Identifying the Targets for Genetic Modification 371
14.3.6.2 Synthesis: Implementing the Targets 374
14.3.6.3 An Example of Metabolic Engineering: The Biosynthesis of Phenol 374
14.3.7 Evolutionary Engineering 375
14.3.8 Protein Engineering 377
14.4 Process Technology Development 378
14.4.1 Conceptual Design 378
14.4.2 Raw Materials 378
14.4.3 Fermentation 379
14.4.3.1 Operation Mode 380
14.4.3.2 Growth Limitation 380
14.4.3.3 Aerobic/Anaerobic Fermentation 380
14.4.3.4 Scale Up 381
14.4.3.5 Cell Removal 381
14.4.4 Product Recovery 382
14.4.4.1 Evaporation 382
14.4.4.2 Extraction and Reactive Extraction 382
14.4.4.3 Precipitation 383
14.4.4.4 Acidification and Crystallization 384
14.4.4.5 Chromatography 384
14.4.4.6 Electrodialysis 384
14.4.5 Purification 384
14.5 The Integrated Approach: Developing Microbiology and Process Technology in Parallel 384
14.5.1 Product Inhibition 385
14.5.2 Fermentation Operating Mode 385
14.5.3 Unit Operations in the Downstream Part of the Plant 386
14.5.4 Holistic Understanding of Biology and Process Technology 386
14.6 Conclusions 387
Acknowledgements 387
References 387
Chapter 15 - Trends and Perspectives in Green Chemistry and White Biotechnology 391
15.1 Ultrasound 391
15.2 Fluorous Solvents 393
15.3 Aphrons 396
15.4 Glycols 398
15.4.1 Glymes 398
15.4.2 Liquid Polymers 399
15.5 Alkyl Carbonates 400
15.6 Other Applications 402
15.6.1 Tunable Solvents 402
15.6.2 Biodesalination 403
15.6.3 Nanotechnology 404
References 405
Subject Index 409

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