GREEN CHEMISTRY AND ENGINEERING

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3 GREEN CHEMISTRY AND ENGINEERING

5 GREEN CHEMISTRY AND ENGINEERING A Practical Design Approach CONCEPCIÓN JIMÉNEZ-GONZÁLEZ DAVID J. C. CONSTABLE

6 Copyright Ó 2011 by John Wiley & Sons, Inc. All rights reserved. Published by John Wiley & Sons, Inc., Hoboken, New Jersey. Published simultaneously in Canada. No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, scanning, or otherwise, except as permitted under Section 107 or 108 of the 1976 United States Copyright Act, without either the prior written permission of the Publisher, or authorization through payment of the appropriate per-copy fee to the Copyright Clearance Center, Inc., 222 Rosewood Drive, Danvers, MA 01923, (978) , fax (978) , or on the web at Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030, (201) , fax (201) , or online at Limit of Liability/Disclaimer of Warranty: While the publisher and author have used their best efforts in preparing this book, they make no representations or warranties with respect to the accuracy or completeness of the contents of this book and specifically disclaim any implied warranties of merchantability or fitness for a particular purpose. No warranty may be created or extended by sales representatives or written sales materials. The advice and strategies contained herein may not be suitable for your situation. You should consult with a professional where appropriate. Neither the publisher nor author shall be liable for any loss of profit or any other commercial damages, including but not limited to special, incidental, consequential, or other damages. For general information on our other products and services or for technical support, please contact our Customer Care Department within the United States at (800) , outside the United States at (317) or fax (317) Wiley also publishes its books in a variety of electronic formats. Some content that appears in print may not be available in electronic formats. For more information about Wiley products, visit our web site at Library of Congress Cataloging-in-Publication Data: Jimenez-Gonzalez, Concepción Conchita. Green chemistry and engineering : a practical design approach / Concepción Conchita Jimenez-Gonzalez, David J. C. Constable. p. cm. Includes index. ISBN (cloth) 1. Environmental chemistry Industrial applications. 2. Sustainable engineering. I. Constable, David J. C., II. Title. TP155.2.E58J dc Printed in Singapore

7 CONTENTS PREFACE xi PART I GREEEN CHEMISTRY AND GREEN ENGINEERING IN THE MOVEMENT TOWARD SUSTAINABILITY 1 1 Green Chemistry and Engineering in the Context of Sustainability Why Green Chemistry? Green Chemistry, Green Engineering, and Sustainability Until Death Do Us Part: A Marriage of Disciplines 13 Problems 15 References 15 2 Green Chemistry and Green Engineering Principles Green Chemistry Principles Twelve More Green Chemistry Principles Twelve Principles of Green Engineering The San Destin Declaration: Principles of Green Engineering Simplifying the Principles 34 Problems 38 References 39 3 Starting with the Basics: Integrating Environment, Health, and Safety Environmental Issues of Importance Health Issues of Importance 54 v

8 vi CONTENTS 3.3 Safety Issues of Importance Hazard and Risk Integrated Perspective on Environment, Health, and Safety 70 Problems 70 References 73 4 How Do We Know It s Green? A Metrics Primer General Considerations About Green Chemistry and Engineering Metrics Chemistry Metrics Process Metrics Cost Implications and Green Chemistry Metrics A Final Word on Green Metrics 101 Problems 102 References 103 PART II THE BEGINNING: DESIGNING GREENER, SAFER CHEMICAL SYNTHESES Route and Chemistry Selection The Challenge of Synthetic Chemistry Making Molecules Using Different Chemistries Route Strategy Protection Deprotection Going from a Route to a Process 126 Problems 127 References Material Selection: Solvents, Catalysts, and Reagents Solvents and Solvent Selection Strategies Catalysts and Catalyst Selection Strategies Other Reagents 168 Problems 168 References Reaction Conditions and Green Chemistry Stoichiometry Design of Experiments Temperature Solvent Use Solvents and Energy Use Reaction and Processing Time Order and Rate of Reagent Addition Mixing 189

9 CONTENTS vii Appendix 7.1: Common Practices in Batch Chemical Processing and Their Green Chemistry Impacts 191 Problems 196 References Bioprocesses How Biotechnology Has Been Used Are Bioprocesses Green? What Is Involved in Bioprocessing Examples of Products Obtained from Bioprocessing 216 Problems 226 References 232 PART III FROM THE FLASK TO THE PLANT: DESIGNING GREENER, SAFER, MORE SUSTAINABLE MANUFACTURING PROCESSES Mass and Energy Balances Why We Need Mass Balances, Energy Balances, and Process Flow Diagrams Types of Processes Process Flow Diagams Mass Balances Energy Balances Measuring Greenness of a Process Through Energy and Mass Balances 261 Problems 265 References The Scale-up Effect The Scale-up Problem Factors Affecting Scale-up Scale-up Tools Numbering-up vs. Scaling-up 289 Problems 290 References Reactors and Separations Reactors and Separations in Green Engineering Reactors Separations and Other Unit Operations Batch vs. Continuous Processes Does Size Matter? 323 Problems 323 References 327

10 viii CONTENTS 12 Process Synthesis Process Synthesis Background Process Synthesis Approaches and Green Engineering Evolutionary Techniques Heuristics Methods Hierarchical Decomposition Superstructure and Multiobjective Optimization Synthesis of Subsystems 354 Problems 355 References Mass and Energy Integration Process Integration: Synthesis, Analysis, and Optimization Energy Integration Mass Integration 373 Problems 381 References Inherent Safety Inherent Safety vs. Traditional Process Safety Inherent Safety and Inherently Safer Design Inherent Safety in Route Strategy and Process Design Conclusions on Inherent Safety 406 Problems 406 References Process Intensification Process Intensification Background Process Intensification Technologies Process Intensification Techniques Perspectives on Process Intensification 437 Problems 437 References 442 PART IV EXPANDING THE BOUNDARIES Life Cycle Inventory and Assessment Concepts Life Cycle Inventory and Assessment Background LCI/A Methodology Interpretation: Making Decisions with LCI/A Streamlined Life Cycle Assessment 481 Problems 484 References 488

11 CONTENTS ix 17 Impacts of Materials and Procurement Life Cycle Management Where Chemical Trees and Supply Chains Come From Green (Sustainable) Procurement Transportation Impacts 511 Problems 515 References Impacts of Energy Requirements Where Energy Comes From Environmental Life Cycle Emissions and Impacts of Energy Generation From Emissions to Impacts Energy Requirements for Waste Treatment 540 Problems 540 References Impacts of Waste and Waste Treatment Environmental Fate and Effects Data Environmental Fate Information: Physical Properties Environmental Fate Information: Transformation and Depletion Mechanisms Environmental Effects Information Environmental Risk Assessment Environmental Life Cycle Impacts of Waste Treatment 565 Problems 574 References Total Cost Assessment Total Cost Assessment Background Importance of Total Cost Assessment Relationship Between Life Cycle Inventory/Assessment and Total Cost Assessment Timing of a Total Cost Assessment Total Cost Assessment Methodology Total Cost Assessment in a Green Chemistry Context 589 Problems 594 References 597 PART V WHAT LIES AHEAD Emerging Materials Emerging Materials Development Nanomaterials 602

12 x CONTENTS 21.3 Bioplastics and Biopolymers About New Green Materials 609 Problems 609 References Renewable Resources Why We Need Renewable Resources Renewable Materials The Biorefinery Renewable Energy 625 Problems 630 References Evaluating Technologies Why We Need to Evaluate Technologies and Processes Comprehensively Comparing Technologies and Processes One Way to Compare Technologies Trade-Offs Advantages and Limitations of Comparing Technologies 645 Problems 646 References Industrial Ecology Industrial Ecology Background Principles and Concepts of Industrial Ecology and Design Industrial Ecology and Design Industrial Ecology in Practice 663 Problems 665 References Tying It All Together: Is Sustainability Possible? Can Green Chemistry and Green Engineering Enable Sustainability? Sustainability: Culture and Policy Influencing Sustainability Moving to Action 674 Problems 674 References 675 INDEX 677

13 PREFACE In the last decade, interest in and understanding of green chemistry and green engineering have increased steadily beyond academia and into the business world. Industries within different sectors of the economy have made concerted efforts to embed these concepts in their operations. Given our experience with green chemistry and green engineering in the pharmaceutical industry, we were initially approached by the publishers to edit a book on green chemistry in the pharmaceutical industry. This was a worthy proposal, but we felt that we had a greater opportunity and worthier endeavor to produce a book that would attempt to fully integrate green chemistry and green engineering into the academic curricula and that at the same time could serve as a practical reference to chemists and engineers in the workplace. Green chemistry and green engineering are still relatively new areas that have not been completely ingrained in traditional chemistry and engineering curricula, but classes and even majors in these topics are becoming increasingly common. However, most classes in green chemistry are taught from an environmental chemistry perspective or a synthetic organic chemistry perspective, with neither approach addressing issues of manufacturing or manufacturability of products. Green engineering classes, on the other hand, tend to emphasize issues related to manufacturing, but do not treat reaction and process chemistry sufficiently, so these disciplines still seem to be disconnected. This lack of integration between chemistry, engineering, and other key disciplines has been one of the main challenges that we have had within the industrial workplace and in previous academic experiences. As a consequence of these experiences, we decided to write this book to bridge the great divide between bench chemistry, process design, engineering, environment, health, safety, and life cycle considerations. We felt that a systems-oriented and integrated approach was needed to evolve green chemistry and green engineering as disciplines in the broader context of sustainability. To achieve this, we have organized the book in five main sections. xi

14 xii PREFACE. Part I. Green Chemistry and Green Engineering in the Movement Toward Sustainability. Chapters 1 to 4 set the broader context of sustainability, highlighting the key role that green chemistry and green engineering have in moving society toward the adoption of more sustainable practices in providing key items of commerce.. Part II. The Beginning: Designing Greener, Safer Chemical Synthesis. Chapters 5 to 8 address the key components of chemistry that will contribute to the achievement of more sustainable chemical reactions and reaction pathways. They also provide an approach to materials selection that promotes the overall greenness of a chemical synthesis without diminishing the efficiency of the chemistry or associated chemical process.. Part III. From the Flask to the Plant: Designing Greener, Safer, More Sustainable Manufacturing Processes. Chapters 9 to 15 provide those key engineering concepts that support the design of greener, more sustainable chemical processes.. Part IV. Expanding the Boundaries: Looking Beyond Our Processes. Chapters 16 to 20 introduce a life cycle thinking perspective by providing background and context for placing a particular chemical process in the broader chemical enterprise, including its impacts from raw materials extraction to recycle/reuse or end-of-life considerations.. Part V. What Lies Ahead: Beyond the Chemical Processing Technology of Today or Delivering Tomorrow s Products More Sustainably. Finally, Chapters 21 to 25 provide some indication of trends in chemical processing that may lead us toward more sustainable practices. To help provide a practical approach, we have included examples and exercises that will help the student or practitioner to understand these concepts as applied to the industrial setting and to use the material in direct and indirect applications. The exercises are intended to make the book suitable for both self-study or as a textbook, and most exercises are derived from our professional experiences. The book is an outgrowth of our experience in applied and fundamental research, consulting, teaching, and corporate work on the areas of green chemistry, green engineering, and sustainability. It is intended primarily for graduate and senior-level courses in chemistry and chemical engineering, although we believe that chemists and engineers working in manufacturing, research, and development, especially in the fine-chemical and pharmaceutical areas, will find the book to be a useful reference for process design and reengineering. Our aim is to provide a balance between academic needs and practical industrial applications of an integrated approach to green chemistry and green engineering in the context of sustainability. Acknowledgments We thank all our colleagues who have contributed directly or indirectly to our journey toward sustainability, and whose ideas and collaborations throughout the years have contributed to our own experience in the areas of green chemistry and green engineering. We also express our gratitude to GlaxoSmithKline, in general, and to James R. Hagan, in particular, for their support and encouragement.

15 PREFACE xiii We also give special thanks to Rafiqul Gani and Ana Carvalho from the Computer Aided Process-Product Engineering Center, Department of Chemical and Biochemical Engineering at the Technical University of Denmark, for their comments, reviews, and contributions to Chapter 12; to Mariana Pierobon and BASF for their helpful comments and for allowing us to use one of BASF s eco-efficiency assessments as an example in the life cycle chapters; to Sara Conradt for allowing us to use a sample of her masters thesis as an example of LCA outputs; and to Tom Roper and John Hayler at GSK for their feedback on green chemistry throughout the years. Finally, we want to thank Chemical Engineering magazine, the American Chemical Society, Springer Science and Business Media, Elsevier, John Wiley & Sons, the Royal Society of Chemistry, and Wiley-VCH for permission to reproduce some printed material. December 2009 CONCEPCIÓN JIMENEZ-GONZALEZ DAVID J. C. CONSTABLE

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