Green Metrics, Volume 11

Paul T. Anastas joined Yale University as Professor and iserves as the Director of the Center for Green Chemistry and Green Engineering at Yale. From 2004-2006, Paul Anastas has been the Director of the Green Chemistry Institute in Washington, D.C. Until June of 2004 he served as Assistant Director for Environment at e White House Office of Science and Technology Policy where his responsibilities included a wide range of environmental science issues including furthering international public-private cooperation in areas of Science for Sustainability such as Green Chemistry. In 1991, he established the industry-government-university partnership Green Chemistry Program, which was expanded to include basic research, and the Presidential Green Chemistry Challenge Awards. He has published and edited several books in the field of Green Chemistry and is one of the inventors of the 12 principles of Green Chemistry. David J.C. Constable is the Director the American Chemical Society´s Green Chemistry Institute®. From the end of September, 2011 until January, 2013 David worked as the owner and principal at Sustainability Foresights, LLC. David left Lockheed Martin as the Corporate Vice President of Energy, Environment, Safety & Health (ESH) at the end of September 2011. Prior to joining Lockheed Martin, David was the Director of Operational Sustainability in the Corporate Environment, Health, and Safety Department at GlaxoSmithKline.During David´s tenure with GlaxoSmithKline, he held positions of increasing responsibility and global reach within Corporate Environment, Health and Safety. He first joined SmithKline Beecham, a predecessor to GlaxoSmithKline, in 1991. Prior to joining SmithKline Beecham, he served as a Group Leader in the SHEA Analytical Services group of ICI Americas. Dr. Jiménez-González is currently Director of New Product Development at Stiefel, a GlaxoSmithKline company. She has worked in GlaxoSmithKline for about 14 years in a variety of roles of increasing responsibility, most recently Director of Engagement, Planning, Analysis and Reporting and Director of Operational Sustainability leading teams responsible for the global programs to embed Sustainability into the operations, the Sustainability external reporting and the Environment, Health and Safety (EHS) strategic plan. Before joining GSK, she was program manager at the Environmental Quality Center of the Monterrey Institute of Technology and Superior Education (ITESM), and worked in several EHS and sustainability positions in Mexico. She currently also teaches Green Chemical Engineering at North Carolina State University (NCSU). In the past she was a faculty member at ITESM and visiting faculty in the Saltillo Institute of Technology, Mexico. She has a B.S. in Chemical and Industrial Eng. from the Chihuahua Institute of Technology (Mexico); a M.Sc. in Environmental Eng. from ITESM, Mexico; and a PhD in Chemical Engineering from NCSU. Her publications involve topics in the area of life cycle assessment, material selection, green chemistry, energy optimization, much of the publications as a result of GlaxoSmithKlines research.

• List of Contributors XIPreface XIII1 Green Chemistry Metrics 1David J.C. Constable1.1 Introduction and General Considerations 11.2 Feedstocks 51.3 Chemicals 61.3.1 Hazard and Risk 61.4 General Chemistry Considerations and Chemistry Metrics 101.5 Evolution of Green Chemistry Metrics 111.6 Andraos: Tree Analysis 141.7 Process Metrics 151.8 Product Metrics 161.9 Sustainability and Green Chemistry 171.10 Making Decisions 18References 192 Expanding Rational Molecular Design beyond Pharma: Metrics to Guide Safer Chemical Design 29Nicholas D. Anastas, John Leazer, Michael A. Gonzalez, and Stephen C. DeVito2.1 Introduction to Safer Chemical Design 292.2 Life Cycle Thinking 302.2.1 Sustainability, Green Chemistry, and Green Engineering 302.2.2 Life Cycle Considerations 312.2.3 Life Cycle Assessment 322.2.4 Chemical Process Sustainability Evaluation – Metrics 342.3 Attributes of Chemicals of Good Character 362.4 Tools for Characterizing the Attributes of Chemicals of Good2.4.1 Strive to Reduce or Eliminate the Use of Chemicals 402.4.2 Maximize Biological and Use Potency and Efficacy 402.4.3 Strive for Economic Efficiency 402.4.4 Limited Bioavailability 412.4.5 Limited Environmental Mobility 412.4.6 Design for Selective Reactivity: Toxicity 412.4.7 Minimize the Incorporation of Known Hazardous Functional Groups: Toxicophores and Isosteres 422.4.8 Minimize the Use of Toxic Solvents 422.4.9 Limited Persistence and Bioaccumulation 432.4.10 Quick Transformation to Innocuous Products 442.4.11 Avoid Extremes of pH 442.5 A Decision Framework 442.5.1 A Suggested Protocol for Approaching Safer Chemical Design 452.5.2 Alternatives and Chemical Risk Assessment 452.6 The Road Ahead: Training of a Twenty-First Century Chemist 46References 463 Key Metrics to Inform Chemical Synthesis Route Design 49John Andraos and Andrei Hent3.1 Introduction 493.2 Material Efficiency Analysis for Synthesis Plans 503.3 Case Study I: Bortezomib 563.3.1 Millennium Pharmaceuticals’ Process 593.3.2 Pharma-Sintez Process 623.3.3 Material Efficiency – Local and Express 643.3.4 Synthesis Strategy for Future Optimization 723.3.5 Summary 733.4 Case Study II: Aspirin 743.4.1 Reaction Network 743.4.2 Material Efficiency 763.4.3 Environmental and Safety–Hazard Impact 783.4.4 Input Energy 843.4.5 Case I 843.4.6 Case II 853.4.7 Case III 853.4.8 Case IV 853.4.9 Case V 863.4.10 Case VI 863.4.11 Concluding Remarks and Outlook for Improvements 88References 914 Life Cycle Assessment 95Concepción Jiménez-González4.1 Introduction 954.2 The Evolution of Life Cycle Assessment 964.3 LCA Methodology at a Glance 974.3.1 Goal and Scope 984.3.2 Inventory Analysis 984.3.3 Impact Assessment 994.3.4 Interpretation 994.3.5 LCI/A Limitations 1004.3.6 Critical Review 1014.3.7 Streamlined Life Cycle Assessment 1024.4 Measuring Greenness with LCI/A – Applications 1034.4.1 Probing Case Studies 1034.4.2 Chemical Route Comparison 1064.4.3 Material Assessment 1094.4.4 Product LCAs 1124.4.5 Footprinting 1154.5 Final Remarks 117References 1185 Sustainable Design of Batch Processes 125Tânia Pinto-Varela and Ana Isabel Carvalho5.1 Introduction 1255.2 State of the Art 1265.2.1 Design and Retrofit of Batch Processes 1275.2.2 Sustainability Assessment 1315.3 Framework for Design and Retrofitting in Batch Processes 1365.3.1 Economic Assessment 1385.3.2 Environmental Assessment 1395.3.3 Social Assessment 1405.3.4 Methodologies 1415.4 Case Studies 1425.4.1 Retrofit Sustainable Batch Design 1425.4.2 Design of Batch Process 1475.5 Conclusions 150References 1526 Green Chemistry Metrics and Life Cycle Assessment for Microflow Continuous Processing 157Lihua Zhang, Qi Wang, and Volker Hessel6.1 Introduction 1576.1.1 Green Chemistry and Green Engineering in the Pharmaceutical Industry 1576.1.2 Green Metrics and Life Cycle Assessment 1586.1.3 Continuous Processing at Small Scale 1596.2 Environmental Analysis through Green Chemistry Metrics and Life Cycle Assessment 1626.2.1 Green Chemistry Metrics 1626.2.2 Life Cycle Assessment (LCA) 1636.3 Application of Green Chemistry Metrics and Life Cycle Assessmentto Assess Microflow Processing 1636.3.1 Use as Benchmarking Tool for Continuous versus Batch; at Lab and Production Scale 1646.3.2 Use as Decision Support Tool for Single Innovation Drivers – Choice of Type of Microreactor and Type of a Catalyst (Including Use/Not Use) 1676.3.2.1 Reaction Conditions of Batch Process and Continuous Microflow Process 1676.3.2.2 SLCA Results 1686.3.2.3 Economic Evaluation 1706.3.2.4 Conclusions 1716.3.3 Use as Decision Support Tool for Single Innovation Drivers – Solvent Choice and Role of Recycling 1716.3.4 Use as Decision Support Tool for Bundled Innovation Drivers Such as Multifacetted Process Optimization versus Process Intensification 1746.3.4.1 API Production Process at Sanofi 1746.3.4.2 Process Alternatives for Optimization and Intensification 1746.3.4.3 Ecological Profile Comparison of Crude Batch and Continuous Operation 1756.3.4.4 Cost Analysis of Batch and Continuous Operation 1786.3.4.5 Conclusions 1796.3.5 Cascading Reactions Into a Microreactor Flow Network – Greenness of Multistep Reaction/Separation Integration 1796.3.5.1 LCA Study for Single-Step Analyses in Batch and Flow 1816.3.5.2 LCA Study for “Two-Reactor Network” Process Designs 1846.3.5.3 LCA Study for “Three-Reaction Network” Process Designs 1846.3.6 Use as Process-Design Guidance and Benchmarking Tool Against Conventional Processes 1866.3.6.1 Process Simulation and CAPEX Cost Study 1886.3.6.2 LCA for Continuous Flow Synthesis of ADA 1906.3.6.3 LCA for Two-Step Conventional Synthesis of ADA 1916.3.6.4 Complete LCA Picture 1916.3.6.5 Green Metrics Compared for the Direct Microflow Route and Conventional Two-Step Route 1926.3.6.6 Conclusions 1946.4 Economic Analysis and Snapshot on Applications with Continuous Microflow Processing 1956.4.1 Life Cycle Costing (LCC) 1956.4.2 Snapshot on LCC Applications with Continuous Microflow Processing 1966.5 Conclusions and Outlook 199References 2017 Benchmarking the Sustainability of Biocatalytic Processes 207John M. Woodley7.1 Introduction 2077.2 Biocatalytic Processes 2077.3 Biocatalytic Process Design and Development 2107.4 Sustainability of Biocatalytic Processes 2107.5 Quantitative Measuring of the Sustainability of Biocatalytic Processes 2127.6 Early Stage Sustainability Assessment 2137.6.1 Evaluation of Route Feasibility 2147.6.1.1 Atom Economy 2147.6.1.2 Carbon Mass Efficiency 2147.6.2 Evaluation of Biocatalyst and Reaction Development 2157.6.2.1 Process Mass Intensity 2157.6.2.2 Solvent Intensity 2157.6.2.3 Water Intensity 2167.6.2.4 E-factor 2167.7 Benchmarking 2167.7.1 Route Selection 2167.7.2 Biocatalyst and Reaction Development 2177.8 Examples 2177.8.1 Biocatalytic Route to Atorvastatin 2187.8.2 Biocatalytic Route to Sitagliptin 2197.9 Future Perspectives 2217.9.1 Process Development 2217.9.2 Methodology 2237.10 Concluding Remarks 224References 2258 How Chemical Hazard Assessment in Consumer Products Drives Green Chemistry 231Lauren Heine and Margaret H. Whittaker8.1 Introduction 2318.2 What Drives Consumer Product Companies to Look for Less Hazardous Chemical Ingredients 2328.2.1 Chemical Substitution and Regrettable Substitution 2338.2.2 Nonprofit Organization (NPO) Campaigns 2358.2.3 Retailer Initiatives 2378.2.4 State Initiatives 2408.2.5 Consumer Product Sector Leaders: Setting the Example for Others 2428.3 What is Chemical Hazard Assessment? 2438.3.1 Globally Harmonized System of Classification and Labelling of Chemicals (GHS) 2448.3.2 Comprehensive and Abbreviated Forms of CHA 2478.3.2.1 GreenScreen for Safer Chemicals 2488.3.2.2 Quick Chemical Assessment Tool (QCAT) 2528.3.2.3 GreenScreen List Translator (GS LT) 2538.4 How Chemical Hazard Assessment is Used 2558.4.1 Chemical Footprint Project 2558.4.2 Health Product Declaration Version 2.0 (HPD) 2598.4.3 Red List – Declare Label 2598.4.4 United States Environmental Protection Agency: Safer Choice Program 2608.4.5 International Living Future Institute’s Living Product Challenges 2628.4.6 Cradle to Cradle Certified Product Program 2628.4.7 Chemical Alternatives Assessment 2638.5 Case Studies Showing How CHA Leads to Safer Consumer Products 2648.5.1 Case Study 1. US EPA Safer Choice Product Certification 2648.5.2 Case Study 2. Levi Strauss & Co. Screened Chemistry 2678.5.3 Case Study 3. Development of an Alternative Food Can Liner 2698.6 Challenges: Beyond Chemical Hazard Assessment 2718.6.1 Transparency 2718.6.2 Filling Data Gaps for Existing and Emerging Hazards: Predictive Toxicology and Tox21 2728.6.3 Integrating CHA into Green Product Design 2728.7 Conclusion 274References 2759 Tying it all together to drive Sustainability in the Chemistry Enterprise 281David J.C. Constable and Concepción Jiménez-González9.1 New Areas of Sustainable and Green Chemistry MetricsResearch 286References 290Index 291

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