Green Chemistry

Principles and Case Studies

Felicia A Etzkorn

• Publisher: Royal Society of Chemistry
• Year: 2019
• Print ISBN: 9781788017985
• eBook ISBN: 9781839160165
• Edition: 1
• Topic: Sciences biologiques
• Subtopic: Science environnementale

Green chemistry as a discipline is gaining increasing attention globally, with environmentally conscious students keen to learn how they can contribute to a safer and more sustainable world. Many universities now offer courses or modules specifically on green chemistry – Green Chemistry: Principles and Case Studies is an essential learning resource for those interested in mastering the subject.

Providing a comprehensive overview of the concepts of green chemistry this book engages students with a thorough understanding of what we mean by green chemistry and how it can be put into practice. Structured around the well-known 12 Principles, and firmly grounded in real-world applications and case-studies, this book shows how green chemistry is already being put into practice and prepare them to think about how they can be incorporated into their own work.

Targeted at advanced undergraduate and first-year graduate students with a background in general and organic chemistry, it is a useful resource both for students and for teachers looking to develop new courses.

Contents

1 Prevent Waste

1.1 Green Chemistry: First, Do No Harm

1.2 Better Living Through Chemistry

1.3 Environmental Pollution

1.4 Risk Is a Function of Hazard and Exposure

1.5 Toxicology and Environmental Chemistry

1.6 Life Cycle Analysis

1.7 Case Study: Polylactic Acid (PLA) (NatureWorks^®)

1.8 Resources: The Scientific Literature

1.9 Implementation of Green Chemistry

1.10 Summary

1.11 Problems: Prevent Waste

References

2 Synthetic Efficiency

2.1 Intermediates and Reagents

2.2 Calculating Efficiency

2.3 Case Study: Atom Economical Ibuprofen Process (BHC Company)

2.4 Chirality

2.5 Greener Solutions for Single Stereoisomers

2.6 Case Study: Synthesis of Tamiflu from Shikimic Acid (Nie et al.)

2.7 Multistep Synthetic Efficiency

2.8 Summary

2.9 Problems: Synthetic Efficiency

References

3 Benign Synthesis

3.1 Eliminating Toxins in Synthesis

3.2 Regulatory Frameworks

3.3 Toxicology

3.4 Classifications of Chemical Toxins

3.5 Case Study: Greener Quantum Dot Synthesis (QD Vision)

3.6 Redox Reactions

3.7 Case Study: Fe-tetra-amido Macrocyclic Ligand (TAML™) Oxidation (Collins)

3.8 Case Study: Alcohol Oxidation by O₂ with Cu/TEMPO (Stahl)

3.9 Case Study: Amide Reductions with Silanes and Fe Catalysts (Nagashima)

3.10 Summary

3.11 Problems: Benign Synthesis

Bibliography

References

4 Benign Products

4.1 Benign by Design

4.2 Cradle-to-Cradle

4.3 Toxicology for Products

4.4 Causation

4.5 Regulations

4.6 Methods for Avoiding Toxic Substances in Products

4.7 Persistent Organic Pollutants (POPs)

4.8 Endocrine Disrupters

4.9 Pesticides

4.10 Case Study: Spinosad and Natular (Clarke)

4.11 Toxic Heavy Metals

4.12 Case Study: Yttrium as a Lead Substitute in Electrodeposition (PPG Industries)

4.13 Summary

4.14 Problems: Benign Products

Bibliography

References

5 Avoid Auxiliaries

5.1 Auxiliaries Defined

5.2 Solvent Auxiliaries

5.3 Extraction Auxiliaries

5.4 Chromatography Auxiliaries

5.5 Minimize Auxiliary Substances

5.6 Solvent-free Synthesis

5.7 Case Study: A Solvent-free Biocatalytic Process for Cosmetic and Personal Care Ingredients (Eastman Chemical Co.)

5.8 Selecting Conventional Solvents

5.9 Greener Substitutes for Solvents

5.10 Case Study: Water-based Acrylic-alkyd Technology (Sherwin-Williams Co.)

5.11 Case Study: Hydrogenation of Isophorone in scCO₂ (Nottingham-Swan)

5.12 Summary

5.13 Problems: Avoid Auxiliaries

References

6 Energy Efficiency

6.1 Energy

6.2 Conservation of Energy

6.3 Case Study: Succinic Acid Through Metabolic Engineering (BioAmber)

6.4 Microwaves

6.5 Case Study: Cellulose Processing by Microwave with an Ionic Liquid (Rogers)

6.6 Photochemistry

6.7 Case Study: Ruthenium Photocatalyst (Yoon)

6.8 Battery Technology

6.9 Case Study: Vanadium Redox Flow Battery (UniEnergy Technologies)

6.10 Transformer Technology

6.11 Case Study: Vegetable Oil Dielectric Insulating Fluid for High Voltage Transformers (Cargill)

6.12 Renewable Liquid Fuels

6.13 Solar Photovoltaics

6.14 Summary

6.15 Problems: Energy Efficiency

References

7 Renewable Feedstocks

7.1 Fossil Feedstocks

7.2 Renewable Feedstocks

7.3 Cellulose

7.4 Sugars

7.5 Case Study: Cost-advantaged Production of Intermediate and Basic Chemicals from Renewable Feedstocks (Genomatica)

7.6 Lignins

7.7 Nitrogen: Proteins, Amino Acids, and Nucleic Acids

7.8 Case Study: Production of Biofeedstock Dicarboxylic Acids for Nylon (Verdezyne)

7.9 Case Study: Human Immunodeficiency Virus (HIV) Drug Carbovir from a Purine

7.10 Lipids: Fats and Oils

7.11 Natural Products

7.12 Case Study: Synthesis of Paclitaxel from Pacific Yew Tree Needles

7.13 Summary

7.14 Problems: Renewable Feedstocks

References

8 Avoid Protecting Groups

8.1 Derivatives

8.2 Renewable Feedstocks

8.3 Reactive Functional Groups

8.4 Case Study: Convergent Synthesis of an α-Hydroxyamide (Etzkorn)

8.5 Case Study: An Efficient Biocatalytic Process for Simvastatin Manufacture (Codexis-Tang)

8.6 Protecting-group-free Synthesis

8.7 Case Study: Synthesis of Ambiguine H Without Protecting Groups (Baran)

8.8 Convergent Synthesis

8.9 Case Study: Convergent Synthesis of Swinholide A (Krische)

8.10 Summary

8.11 Problems: Avoid Protecting Groups

References

9 Catalysis

9.1 Catalysts Accelerate Reactions

9.2 Enzymes: Nature's Catalysts Are Proteins

9.3 Advantages of Catalysts

9.4 Case Study: Greener Manufacturing of Sitagliptin Enabled by an Evolved Transaminase (Merck–Codexis)

9.5 Earth-abundant Metal Catalysts

9.6 Catalytic Mechanisms

9.7 Case Study: Using Metathesis Catalysis to Produce High-performing, Green Specialty Chemicals at Advantageous Costs (Elevance)

9.8 Catalyst Reuseability

9.9 Summary

9.10 Problems: Catalysis

References

10 Degradation or Recovery

10.1 Biological and Industrial Cycles

10.2 Case Study: Biodegradable Polymers from Carbon Monoxide (Coates)

10.3 The Great Pacific Garbage Patch

10.4 Case Study: Water-degradable Plastics (Miller)

10.5 Case Study: Bacterial Degradation of Polyethylene Terephthalate (Miyamoto-Oda)

10.6 Case Study: Biodegradable Surfactants and Sugars Replace Very Persistent Fluorinated Surfactants in Aqueous Firefighting Foams (Solberg Co.)

10.7 Metals Recovery

10.8 Case Study: Recovery of Ecocatalysts from Plants (Grison)

10.9 Summary

10.10 Problems: Degradation or Recovery

References

11 Real-time Analysis

11.1 Real-time Analysis

11.2 Control Parameters

11.3 Reaction Monitoring

11.4 Case Study: Highly Reactive Polyisobutylene (Soltex)

11.5 Spectral Methods

11.6 Case Study: 3D TRASAR^® Cooling System Chemistry and Control (Nalco)

11.7 Chromatographic Methods

11.8 Reactor Design

11.9 Case Study: Kilogram-scale Prexasertib Monolactate Monohydrate Synthesis Under Continuous Flow CGMP Conditions (Ely-Lilly & Co.)

11.10 Summary

11.11 Problems: Real-time Analysis

References

12 Prevent Accidents

12.1 Eliminate Hazards

12.2 Types of Chemical Hazards

12.3 Global Harmonization System

12.4 Elimin...

Table of contents

• Cover
• Title
• Copyright
• Preface
• Acknowledgements
• Dedication Dedication
• The 12 Principles of Green Chemistry The 12 Principles of Green Chemistry
• Contents
• Subject Index