Handbook of Green Chemistry volume 11: Green Metrics

Green Metrics......Page 1
Contents......Page 7
List of Contributors......Page 13
Preface......Page 15
1.1 Introduction and General Considerations......Page 17
1.2 Feedstocks......Page 21
1.3.1 Hazard and Risk......Page 22
1.4 General Chemistry Considerations and Chemistry Metrics......Page 26
1.5 Evolution of Green Chemistry Metrics......Page 27
1.6 Andraos: Tree Analysis......Page 30
1.7 Process Metrics......Page 31
1.8 Product Metrics......Page 32
1.9 Sustainability and Green Chemistry......Page 33
1.10 Making Decisions......Page 34
References......Page 35
2.1 Introduction to Safer Chemical Design......Page 45
2.2.1 Sustainability, Green Chemistry, and Green Engineering......Page 46
2.2.2 Life Cycle Considerations......Page 47
2.2.3 Life Cycle Assessment......Page 48
2.2.4 Chemical Process Sustainability Evaluation - Metrics......Page 50
2.3 Attributes of Chemicals of Good Character......Page 52
2.4 Tools for Characterizing the Attributes of Chemicals of Good Character......Page 53
2.4.3 Strive for Economic Efficiency......Page 56
2.4.6 Design for Selective Reactivity: Toxicity......Page 57
2.4.8 Minimize the Use of Toxic Solvents......Page 58
2.4.9 Limited Persistence and Bioaccumulation......Page 59
2.5 A Decision Framework......Page 60
2.5.2 Alternatives and Chemical Risk Assessment......Page 61
References......Page 62
3.1 Introduction......Page 65
3.2 Material Efficiency Analysis for Synthesis Plans......Page 66
3.3 Case Study I: Bortezomib......Page 72
3.3.1 Millennium Pharmaceuticals' Process......Page 75
3.3.2 Pharma-Sintez Process......Page 78
3.3.3 Material Efficiency - Local and Express......Page 80
3.3.4 Synthesis Strategy for Future Optimization......Page 88
3.3.5 Summary......Page 89
3.4.1 Reaction Network......Page 90
3.4.2 Material Efficiency......Page 92
3.4.3 Environmental and Safety-Hazard Impact......Page 94
3.4.5 Case I......Page 100
3.4.8 Case IV......Page 101
3.4.10 Case VI......Page 102
3.4.11 Concluding Remarks and Outlook for Improvements......Page 104
References......Page 107
4.1 Introduction......Page 111
4.2 The Evolution of Life Cycle Assessment......Page 112
4.3 LCA Methodology at a Glance......Page 113
4.3.2 Inventory Analysis......Page 114
4.3.4 Interpretation......Page 115
4.3.5 LCI/A Limitations......Page 116
4.3.6 Critical Review......Page 117
4.3.7 Streamlined Life Cycle Assessment......Page 118
4.4.1 Probing case studies......Page 119
4.4.2 Chemical Route Comparison......Page 122
4.4.3 Material Assessment......Page 125
4.4.4 Product LCAs......Page 128
4.4.5 Footprinting......Page 131
4.5 Final Remarks......Page 133
References......Page 134
5.1 Introduction......Page 141
5.2 State of the Art......Page 142
5.2.1 Design and Retrofit of Batch Processes......Page 143
5.2.2 Sustainability Assessment......Page 147
5.3 Framework for Design and Retrofitting in Batch Processes......Page 152
5.3.1 Economic Assessment......Page 154
5.3.2 Environmental Assessment......Page 155
5.3.3 Social Assessment......Page 156
5.3.4 Methodologies......Page 157
5.4.1 Retrofit Sustainable Batch Design......Page 158
5.4.2 Design of Batch Process......Page 163
5.5 Conclusions......Page 166
References......Page 168
6.1.1 Green Chemistry and Green Engineering in the Pharmaceutical Industry......Page 173
6.1.2 Green Metrics and Life Cycle Assessment......Page 174
6.1.3 Continuous Processing at Small Scale......Page 175
6.2.1 Green Chemistry Metrics......Page 178
6.3 Application of Green Chemistry Metrics and Life Cycle Assessment to Assess Microflow Processing......Page 179
6.3.1 Use as Benchmarking Tool for Continuous versus Batch; at Lab and Production Scale......Page 180
6.3.2.1 Reaction Conditions of Batch Process and Continuous Microflow Process......Page 183
6.3.2.2 SLCA Results......Page 184
6.3.2.3 Economic Evaluation......Page 186
6.3.3 Use as Decision Support Tool for Single Innovation Drivers - Solvent Choice and Role of Recycling......Page 187
6.3.4.2 Process Alternatives for Optimization and Intensification......Page 190
6.3.4.3 Ecological Profile Comparison of Crude Batch and Continuous Operation......Page 191
6.3.4.4 Cost Analysis of Batch and Continuous Operation......Page 194
6.3.5 Cascading Reactions Into a Microreactor Flow Network - Greenness of Multistep Reaction/Separation Integration......Page 195
6.3.5.1 LCA Study for Single-Step Analyses in Batch and Flow......Page 197
6.3.5.3 LCA Study for ``Three-Reaction Network´´ Process Designs......Page 200
6.3.6 Use as Process-Design Guidance and Benchmarking Tool Against Conventional Processes......Page 202
6.3.6.1 Process Simulation and CAPEX Cost Study......Page 204
6.3.6.2 LCA for Continuous Flow Synthesis of ADA......Page 206
6.3.6.4 Complete LCA Picture......Page 207
6.3.6.5 Green Metrics Compared for the Direct Microflow Route and Conventional Two-Step Route......Page 208
6.3.6.6 Conclusions......Page 210
6.4.1 Life Cycle Costing (LCC)......Page 211
6.4.2 Snapshot on LCC Applications with Continuous Microflow Processing......Page 212
6.5 Conclusions and Outlook......Page 215
References......Page 217
7.2 Biocatalytic Processes......Page 223
7.4 Sustainability of Biocatalytic Processes......Page 226
7.5 Quantitative Measuring of the Sustainability of Biocatalytic Processes......Page 228
7.6 Early Stage Sustainability Assessment......Page 229
7.6.1.2 Carbon Mass Efficiency......Page 230
7.6.2.2 Solvent Intensity......Page 231
7.7.1 Route Selection......Page 232
7.8 Examples......Page 233
7.8.1 Biocatalytic Route to Atorvastatin......Page 234
7.8.2 Biocatalytic Route to Sitagliptin......Page 235
7.9.1 Process Development......Page 237
7.9.2 Methodology......Page 239
7.10 Concluding Remarks......Page 240
References......Page 241
8.1 Introduction......Page 247
8.2 What Drives Consumer Product Companies to Look for Less Hazardous Chemical Ingredients......Page 248
8.2.1 Chemical Substitution and Regrettable Substitution......Page 249
8.2.2 Nonprofit Organization (NPO) Campaigns......Page 251
8.2.3 Retailer Initiatives......Page 253
8.2.4 State Initiatives......Page 256
8.2.5 Consumer Product Sector Leaders: Setting the Example for Others......Page 258
8.3 What is Chemical Hazard Assessment?......Page 259
8.3.1 Globally Harmonized System of Classification and Labelling of Chemicals (GHS)......Page 260
8.3.2 Comprehensive and Abbreviated Forms of CHA......Page 263
8.3.2.1 GreenScreen for Safer Chemicals......Page 264
8.3.2.2 Quick Chemical Assessment Tool (QCAT)......Page 268
8.3.2.3 GreenScreen List Translator (GS LT)......Page 269
8.4.1 Chemical Footprint Project......Page 271
8.4.3 Red List – Declare Label......Page 275
8.4.4 United States Environmental Protection Agency: Safer Choice Program......Page 276
8.4.6 Cradle to Cradle Certified Product Program......Page 278
8.4.7 Chemical Alternatives Assessment......Page 279
8.5.1 Case Study 1. US EPA Safer Choice Product Certification......Page 280
8.5.2 Case Study 2. Levi Strauss & Co. Screened Chemistry......Page 283
8.5.3 Case Study 3. Development of an Alternative Food Can Liner......Page 285
8.6.1 Transparency......Page 287
8.6.3 Integrating CHA into Green Product Design......Page 288
8.7 Conclusion......Page 290
References......Page 291
Chapter 9: Tying it all together to drive Sustainability in the Chemistry Enterprise......Page 297
9.1 New Areas of Sustainable and Green Chemistry Metrics Research......Page 302
References......Page 306
Index......Page 307
End User License Agreement......Page 317