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Sustainability and Environmental Chemistry

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This hip and professional Google Slides and PowerPoint template illustrates environmental chemistry and its connection with sustainability. Set against a white background, it features engaging green chemistry graphics that will pique the audience's interest. Offering a suite of easy-to-understand visuals and diagrams to demonstrate the complex facets of environmental chemistry, this slide deck will make your presentation stand out. It's user-friendly and fully customizable, ensuring your next talk on environment preservation will not only inform but also inspire!

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Beyond Benign

Green Chemistry Education

HE Green Chemistry

August 13, 2019

Green Chemistry University Curriculum

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General Chemistry

Organic Chemistry

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All Course Materials for the Green Chemistry University Curriculum

August 23, 2019

The Yale-UNIDO University Curriculum is a semester long course developed in collaboration with Beyond Benign. This free course is designed for undergraduate students and teaches (i) how the principles of green chemistry can help resolve global human health and environmental issues, (ii) how green chemistry functions and (iii) how it is implemented. The curriculum was developed as part of the Global Green Chemistry Initiative (GGCI), a joint initiative between the Center for Green Chemistry and Engineering at Yale and the United Nations Industrial Development Organization (UNIDO), and was funded by GEF (Global Environment Facility). The GGCI consists of six primary projects to raise awareness and provide instruction and information on green chemistry. You can find more information at  https://www.global-green-chemistry-initiative.com/

All course materials can be downloaded here

Download Lesson

Course Syllabus

August 21, 2019

This course will explore the fundamentals of chemistry, how chemistry can help address global human health and environmental issues. It provides an introduction to the foundational principles of chemistry including atoms, molecules, chemical reactions, stoichiometry, chemical/physical properties, and periodic table trends. This knowledge is then related to various environmental and human health issues, and develop the appropriate solutions using green chemistry approaches covered in the course.

Lecture 01 – Course Introduction and Accidents and Their Unintentional Consequences

In this lecture students will learn about the course requirements and the innovative capabilities of Green Chemistry which will be covered during next 14 weeks. Students will also learn that accidents can be reduced or prevented with a thoughtful design using Green Chemistry principles.

Lesson download includes:

Lesson Plan: Lecture 1

PowerPoint Presentation: Lecture 1

Content Preview: Course Introduction, Chemical Plant Disasters, Consumer Products (DDT and BPA/Endocrine Disruptors), Why do Green Chemistry?

Optional/Supplemental Readings: Bhopal Plant Disaster Situation Summary

Lecture 02 – Green Chemistry: Reimagining Chemistry

In this class students will learn the definition of Green Chemistry and reflect on the last 25 years of Green Chemistry innovation. They will also explore the main drivers to implement Green Chemistry throughout the world and some of the latest Green Chemistry trends.

Lesson Plan: Lecture 2

PowerPoint Presentation: Lecture 2

Content Preview: What is Green Chemistry? 12 Principles of Green Chemistry, What drives Green Chemistry? 25 Years of Progress and The Future of Green Chemistry

Lecture 03 – 12 Principles of Green Chemistry

In this lecture students will learn about the 12 Green Chemistry Principles and explore industrial examples of implementing the principles.

Lesson Plan 3: 12 Principles of Green Chemistry

PowerPoint Presentation 3: 12 Principles of Green Chemistry

Class Exercises: Writing the 12 Principles and E-Factor

Reading: Presidential Green Chemistry Awards 1996-2016

Lecture 04 – It All Starts at the Beginning

In this lecture students will refresh their fundamental chemistry knowledge: periodic table and atoms. Knowing fundamentals is vital for understanding the Green Chemistry reactions which will be covered later in the semester.

Lesson Plan 4: It All Starts at the Beginning

PowerPoint Presentation 4: It All Starts at the Beginning

Content Preview: Periodic Table, Why is it useful,  Reading the periodic table, Isotopic Symbols, Atoms to Elements, Periodic Trend, Connection to bonding, Elements: Relevancy to Green Chemistry

Handout: The History of the Atom

Class Exercise: Periodic Table Battleship Game

Lecture 05 – The Molecule

In this lecture, students will be introduced to molecules and how to properly draw and assign nomenclature. This lecture will focus on the fundamental ways to identify molecules and extrapolate to organic nomenclature. Since the majority of the content in later lectures will focus on organic molecules and their functional groups, it is important that student have the skills to name and draw organic structures.

Lesson Plan 5: The Molecule

PowerPoint Presentation 5: The Molecule

Content Preview: Molecules and Compounds, Drawing Molecules, Nomenclature of Molecules, Functional Groups, Properties

Homework #1 & Homework #1 Answer Key

Class Exercise: Molecules and Answer Key

Lesson: Chemical Hazard Awareness and Answer Key

Handouts: Organic Compounds Nomenclature, Organic Molecule Nomenclature Steps, IUPAC Naming System

Activity: Polymers and Models

Lecture 06 – Stoichiometry and Reactions

In this lecture, students will continue to build their chemistry fundamentals. They will practice balancing equations and different types of chemical reactions. Finally, they will learn about biomimicry – an inspiration from nature to build new molecules and products.

Lesson Plan 6: Stoichiometry and Reactions

PowerPoint Presentation 6: Stoichiometry and Reactions 

Content Preview: Stoichiometry & Calculations, Reactions, Important Named Reactions, Lab vs. Nature, Green Chemistry in Perspective, Reagents, solvents, and reactors, Biomimicry

Class Exercises: Reactions Lab, Stoichmetry Challenge, Biomimicry Matching Game

Activities: Biomimicry and Empirical Formula

Case Study: Vitamin C Clock Reaction

Supplemental PowerPoint: Brief Intro To Green Chemistry and Biomimicry

Lecture 07 – Limiting Reagent, Yield, and Atom Economy

In this lecture, students will be introduced to the concepts of limiting reagents, yield, and atom economy. Building upon their working knowledge of balancing equations and stoichiometry, students will apply those core skills to determine the efficiency of reactions based upon molecular factors. This lecture will focus on the fundamental ways molecules are evaluated on their efficacy and extrapolate to the Green Chemistry metrics. Since the majority of the content in this lecture focuses on organic molecules and their functional groups, it is important that student have these skills reinforced by continuing to name and draw organic structures when performing calculations.

Lesson Plan 7: Limiting Reagent, Yield, and Atom Economy

Presentation 7: Limiting Reagent, Yield, and Atom Economy

Content Preview: Limiting Reagent, Theoretical and Percent Yield, Current norm for reaction efficiency, Atom Economy, New Green Chemistry reaction metric, E-Factor

Homework 2: Stoichiometry and Reactions & Key

Class Exercise: Green Synthesis of Ibprofen & Key

Supplemental Materials: The EcoScale as a Framework for Undergraduate Green Chemistry Teaching and Assessment

Lecture 08 – Exam 1

Exam 1 and  Exam 1 Answer Key

Lecture 09 – Sustainability

In this lecture students will learn about what Sustainability is and the common misconceptions among individuals today. The lecture covers the typical myths about Sustainability and provides evidence to justify. Furthermore, the lecture will cover the importance on sustainability in business and the various methods in which green chemistry positively effects business operations.

Lesson Plan 9: Sustainability

Presentation 9: Sustainability

Content Preview: Sustainability – Myths and Facts, Society, Economy, and the Environment, Business and Sustainability, Applying Green Chemistry to Management, Different Models of Sustainability

Lecture 10 – Life Cycle Assessment

In this lecture students will learn about Life Cycle Assessment. The lecture covers the standard framework, theory and real examples of Life Cycle Assessment. LCA is complex process and the purpose of this class is to introduce them to the importance and strengths of performing Life Cycle Assessments.

Lesson Plan 10: Life Cycle Assessment

Presentation 10: Life Cycle Assessment

Content  Preview: Life Cycle Thinking and Life Cycle Assessment (LCA), LCA Example: Laundry Detergent, LCA and Green Chemistry, LCA examples and discussions: i-STAT blood analyzing &  Styrofoam take-out container

Lecture 11 – Renewable Feedstocks

In this class students will learn about renewable feedstocks. More specifically, the lecture will focus on what a renewable feedstock is and the criteria necessary to identify appropriate materials for future feedstock.

Lesson Plan 11: Renewable Feedstocks

PowerPoint Presentation 11: Renewable Feedstocks

Content Preview: What is a Feedstock? Renewable vs. Depleting, Current feedstock consumption, Types of Renewable Feedstocks, CO2, Biomass, Agricultural, Industrial Applications, Challenges and Opportunities

Supplemental Materials: Bakery Waste to Chemicals, Bio-based Polycarbonate, Food Waste Biomass, Polymers of Limone Oxide, Ultrasonic and Catalyst Free Expodiation of Limonene

Lecture 12 – Renewable Feedstocks for Energy

In this lecture students will learn about the role chemistry has on providing a sustainable future. The lecture covers the topic of energy and more sustainable approaches for energy consumption.

Lesson Plan 12: Renewable Feedstocks for Energy

PowerPoint Presentation 12: Renewable Feedstocks for Energy

Content Preview: Petroleum industry ( Energy sources, Energy consumption & demand, Meeting the future energy demands), Biofuels from First Generation Corn-based ethanol & Biodiesel to   Second generation biofuels Cellulosics, oils, grasses to finally  Third and Fourth generation biofuels, Algae

Lecture 13 – Real-World Cases in Green Chemistry

In this class students will learn about successful Green Chemistry technologies that have been awarded by the United States Environmental Protection Agency. Students will have the opportunity to research previous winners and discuss with their fellow classmates.

Lesson Plan 13: Real-World Cases in Green Chemistry

PowerPoint Presentation 13: Real-World Cases in Green Chemistry

Content Preview: What are the Presidential Green Chemistry Challenge Awards? PGCCA Case Studies:

2016: Newlight Technologies, AirCarbon: Greenhouse Gas Transformed into High-Performance Thermoplastic

2012: Buckman International, Inc.: Enzymes Reduce the Energy and Wood Fiber Required to Manufacture High-Quality Paper and Paperboard

2011: Professor Bruce H. Lipshutz, Towards Ending Our Dependence on Organic Solvents

2008: SiGNa Chemistry, Inc.: New Stabilized Alkali Metals for Safer, Sustainable Syntheses

2005: Archer Daniels Midland and Novozymes, NovaLipidTM: Low Trans Fats and Oils Produced by Enzymatic Interesterification of Vegetable Oils Using Lipozyme®

2002: Pfizer re-design of Sertraline (ZOLOFT®)

1996: Dow Chemical Company Designing an Environmentally Safe Marine Antifoulant

Class Activity and Materials: Real-World Cases

Lecture 14 – Designing for Recycling and Degradation

In this class students will learn various processes for recycling and how to leverage it to think of the possibilities to design compounds to biodegrade.

Lesson Plan 14: Designing for Recycling and Degradation

PowerPoint Presentation 14: Designing for Recycling and Degradation

Content Preview: The Waste Treatment Pyramid, Reduced Solvent Use, Waste as a Feedstock, Biodegradation,  Design rules/rules of thumb for biodegradation, Designing Products and/or Waste to Biodegrade

Homework 3: Estimating Biodegradability and Key

Class Exercise: Design for Biodegradability and Predicting Biodegradation

Lecture 15 – Catalysis

In this lecture students will learn about the importance of catalysis and the added benefits it provides in all levels of chemistry. Students will see how catalysts make reactions more efficient by means of the activation energy. More importantly, students will be introduced to alternative types of catalysis that Green Chemistry utilizes to create more environmentally responsible processes.

Lesson Plan 15: Catalysis

PowerPoint Presentation 15: Catalysis

Content Preview: What is Catalysis? Why its important and improves performance, Categories of Catalysis, Homogeneous vs. Heterogeneous, Greener Alternatives for Catalysis, Current Trends for the Next Generation of Catalysts, Additional applications for catalysts

Lecture 16 – Solvents: Understanding Their Role

In this class students will learn the roles and responsibilities that solvent have in chemical transformations. The advantage and disadvantages will be discussed followed the various categories of solvent used today. After learning about the effects of solvent use, student will be introduced to the need for alternative solvents and their role in advancing technology, humans, and the environment.

Lesson Plan 16: Solvents: Understanding Their Role

PowerPoint Presentation 16: Solvents: Understanding Their Role

Content Preview: Learning objectives and outcomes, Understanding solvents, Solvent selection guides, Strategies for solvent replacement

Supplemental Materials: CHEM21 Solvent Selection Guide

Lecture 17 – Working without Solvents

In this class students will learn the possibilities to perform chemical transformations without the presence of an organic solvent. Students will explore alternative methodologies ranging from supercritical fluids to solventless conditions. The goal of this lecture is to not only inform student of alternative methodologies, but to provide real example of how these approaches are used today.

Lesson Plan 17: Working without Solvents

PowerPoint Presentation 17: Working without Solvents

Content Preview: Global Solvent Market, Chemistry without organic solvents, Supercritical Fluids, Ionic Liquids, Aqueous Chemistry, Solvent-Free processes, Mechanochemistry

Homework 4: Solvent Substitution and Key

Readings: Solvent Free Reactivity and Review of Aqueous Organic Reactions

Lecture 18 – Exam 2

Exam 2 and Exam 2 Answer Key

Lecture 19: Green Chemistry and Energy

In this lecture students will learn about the current state of energy production and consumption. Traditional sources of energy include non-renewable sources such as coal and oil. Renewable energy sources will be explored such as biofuels, solar cells and fuel cells. Students will learn how energy is used within the laboratory to heat, cool and for processing, along with alternative energy sources for performing synthetic reactions. The next generation of energy applications will also be discussed.

Lesson Plan 19: Green Chemistry and Energy

PowerPoint Plan 19: Green Chemistry and Energy

Content Preview: Current state of energy consumption: Globally, Source of energy: Power plant – coal, oil, natural gas, Renewable – Biofuels, solar cell, Fuel cells, hydro, etc., Energy in the Laboratory ( Thermal, Cooling, Distillation, Equipment, Synthesis), New Modern Applications

Class Exercise: Synthesis of Biodiesel and Dye Sensitized Solar Cell

Lecture 20 – Green Analytical Chemistry

In this class students will learn about Green Analytical Chemistry. The lecture includes information about analytical method assessment, including tools and techniques for assessing the greenness of methods. The lecture addresses sample preparation, analytical techniques and methods including chromatography and spectroscopy, and Process Analytical Technology (PAT).

Lesson Plan 20: Green Analytical Chemistry

PowerPoint Presentation 20: Green Analytical Chemistry

Content Preview: What is Green Analytical Chemistry? Analytical Method Assessment,  Tools and Techniques for Assessing Greenness of Analytical Methods, Sample Preparation, Analytical Techniques and Methods ( Chromatography,  Spectroscopy, Mass spectrometry) and  Process Analytical Technology (PAT)

Reading: Green Chemistry Metrics

Lecture 21 – Introduction to Toxicology

This lecture introduces toxicology. Students will learn different toxicology terms, including definition, types of toxic compounds, and factors influencing toxicity. At the end of the lecture, students will revise potential toxicology endpoints to molecular features which are derived from the periodic table. In addition to periodic table trends, the lecture also introduces the concept of pKa and links it to a skin irritation through the class activity.

Lesson Plan 21: Introduction to Toxicology

Presentation 21: Introduction to Toxicology

Content Preview: Toxicology definition, Toxicity types, Factors affecting chemical toxicity, Toxicology and the periodic table

Class Exercise: Aqueous and Lipid Solubility, pKa and Skin Irritation with Answer Keys

Handout: Log P, Log Kow and pKa

Lecture 22 – Chemical Exposure and Dosage

In this lecture, students learn components of risk – hazard and exposure and how green chemistry aims to minimize hazard, which ultimately leads to minimizing the risk.  This lecture also defines the concept of dose and how the toxicity testing is currently done through dose-response curves. A small class activity on the dose-response curve for solvents allows student to use their newly learned knowledge on dose-response in practice and a quiz at the end summarizes the key concepts covered during this class period.

Lesson Plan 22: Chemical Exposure and Dosage

Presentation 22: Chemical Exposure and Dosage

Content Preview: Risk Assessment, Hazard, Exposure, Dose, Dose Response Curve, LOAEL, NOAEL, and Reference Dose and Tools for Hazard Characterization

Homework 5: Chemical Exposure and Dose with Key 

Class Exercise: Lettuce Seed Assay and Daphnia Bioassay LD 50

Reading: Toxicology Dose Response

Lecture 23 – Molecular Toxicology

This lecture introduces Absorption, Distribution, Metabolism, and Excretion (ADME) concepts and how chemists can take advantage of physicochemical parameters like logP, molecular weight, and vapor pressure to redesign molecules that won’t absorb into the body, limit distribution, and facilitate metabolism and excretion. These concepts are reinforced by an in-class exercise that explores potential absorption routes by benzene. The lecture also explores new approaches to hazard minimization through molecular design.

Lesson Plan 23: Molecular Toxicology

Presentation 23: Molecular Toxicology

Content Preview: Absorption, Distribution, Metabolism, and Excretion (ADME),  Characteristics of an “ideal chemical”, Approaches to hazard minimization through molecular design

Class Exercise: ADME and Rational Design & Electrophilic Reactions with Answer Keys

Reading for Exercise: Electrophiles in Predictive Toxicology

Lecture 24 – Designing Future Products with Reduced Toxicity

This lecture continues to explore different approaches to hazard minimization by changing molecular design. After several practical examples and a case study, students will learn about current methods that scientists use to assess chemical toxicity on a large scale. In vivo and In vitro studies are discussed.

Lesson Plan 24: Designing Future Products with Reduced Toxicity

PowerPoint Presentation 24: Designing Future Products with Reduced Toxicity

Content Preview: Approaches to hazard minimization through molecular design, Case study: Codexis, Alternatives to animal testing, QSAR-Quantitative Structure Activity Relationship, The nexus of chemistry and toxicology, Sources of high throughput data

Homework 6: Toxicology with examples and answer key

Class Exercise: Using ProTox Class, Glutathione as a Tool, Crossroads of Computation

Reading: Selection of Chemical Alternatives

Lecture 25 & 26: Safe Chemical Design Game

The last two lectures, lecture 25 and lecture 26, allow students to explore safer chemical design and ADME through educational online computer game. The game encourages students to think like professional chemical designers and to develop a chemical product with respect to function and improved human and environmental health. The developed worksheet leads students through the game challenges and tests their understanding of the content as they progress through the game. The eight questions in the worksheet can be used as an individual assignment or as an in-class discussion. These questions are designed to be answered as students play the game.

Lesson Plan 25 & 26: Safe Chemical Design Game

Class Exercise: Safer Chemical Design Game and Answer Key

Reading: The Safer Chemical Design Game

Lecture 27 – Exam 3: Final Exam

Exam 3: Final Exam and Exam 3: Final Exam Answer Key

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What is Green Chemistry

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Developed by Paul Anastas and John Warner in 1998*, the following list outlines a a framework for making a greener chemical, process, or product.

Click on the tabs to reveal articles about each principle. These articles were originally developed for  The Nexus Blog . 

It is better to prevent waste than to treat or clean up waste after it has been created.

Contributed by Berkeley W. Cue, Jr., Ph.D., BWC Pharma Consulting, LLC.

In their publication “ Green Chemistry, Theory and Practice ” in 1998, Anastas and Warner introduced their 12 principles. My view is the first principle, often referred to as the prevention principle, is the most important and the other principles are the “how to’s” to achieve it

An often-used measure of waste is the E-factor , described by Roger Sheldon, which relates the weight of waste coproduced to the weight of the desired product. More recently, the ACS Green Chemistry Institute Pharmaceutical Roundtable ( ACS GCIPR ) has favored process mass intensity , which expresses a ratio of the weights of all materials (water, organic solvents, raw materials, reagents, process aids) used to the weight of the active drug ingredient (API) produced. This is an important roundtable focus because of the historically large amount of waste coproduced during drug manufacturing—more than 100 kilos per kilo of API in many cases. However, when companies apply green chemistry principles to the design of the API process, dramatic reductions in waste are often achieved, sometimes as much as ten-fold. So, it is important to extend the impressive results achieved by the ACS GCIPR to all parts of the drug industry, especially the biopharma and generic sectors, as well as to other sectors of the chemical enterprise where synthetic chemistry is used to produce their products.

More Resources & Examples:

Process Mass Intensity Tool

2012 PGCCA Winner: Codexis, Inc. and Professor Yi Tang, University of California, Los Angeles “ An Efficient Biocatalytic Process to Manufacture Simvastatin ”

2002 PGCCA Winner: Pfizer, Inc. “ Green Chemistry in the Redesign of the Sertraline Process ”

Pharma Strives for Green Goals , Stephen K. Ritter, Chemical & Engineering News, 90(22), May 28, 2012.

Articles Cited:

The E Factor: fifteen years on ; R.A. Sheldon; Green Chem. 2007, (9), pp 1273-1283, DOI: 10.1039/B713736M

Using the Right Green Yardstick: Why Process Mass Intensity Is Used in the Pharmaceutical Industry to Drive More Sustainable Processes ; Concepcion Jimenez-Gonzalez, Celia S. Ponder, Quirinus B. Broxterman, and Julie B. Manley; Org. Process Res. Dev., 2011, 15 (4), pp 912–917, DOI: 10.1021/op200097d.

• Atom Economy

Synthetic methods should be designed to maximize incorporation of all materials used in the process into the final product.

Contributed by Michael Cann, Ph.D., Professor of Chemistry, University of Scranton

The second principle of green chemistry can be simply stated as the “atom economy” of a reaction. Atom economy, which was developed by Barry Trost 1 , asks the question “what atoms of the reactants are incorporated into the final desired product(s) and what atoms are wasted?”

Traditionally, the efficiency of a reaction has been measured by calculating the percent yield. Let us assume that the following substitution reaction gives 100% yield. While this is admirable, we can shed more light on the efficiency of a reaction by calculating the “percent atom economy” as follows:

% Atom Economy = (FW of atoms utilized/FW of all reactants) X 100 = (137/275) X 100 = 50%

The percent atom economy is simply the formula weight of the desired product(s) (compound 4, 137 g/mol) divided by the sum of the formula weights of all the reactants (275 g/mol), which gives 50% in this case. Simply put, even if our percent yield is 100%, only half the mass of the reactants atoms are incorporated in the desired product while the other half is wasted in unwanted by-products. Imagine telling your mom you baked a cake and threw away half the ingredients! Thus chemists must not only strive to achieve maximum percent yield, but also design syntheses that maximize the incorporation of the atoms of the reactants into the desired product.

Principle #2 deals with the reactants. However, as those of us who have run a chemical reaction know, we usually use other materials such as solvents and separating agents during a synthesis. These materials usually make up the bulk of the material input, and thus we must also account for the waste that is produced from them. Stay “tuned” as you will see these discussed in subsequent Principles of Green Chemistry.

Atom Economy: A Measure of the Efficiency of a Reaction . Michael C. Cann and Marc E. Connelly; Real-World Cases in Green Chemistry; ACS, Washington, 2000.

1998 PGCCA Winner: Professor Barry M. Trost of Stanford University, " The Development of the Concept of Atom Economy ."

1. The Atom Economy-A Search for Synthetic Efficiency; Barry M. Trost;  Science  1991, (254), pp 1471-1477.

• Less Hazardous Chemical Syntheses

Wherever practicable, synthetic methods should be designed to use and generate substances that possess little or no toxicity to human health and the environment.

Contributed by David J. C. Constable, Ph.D., Director, ACS Green Chemistry Institute ®

When you think about it, this is a two-part principle divided by the first two words, “wherever practicable.” Saying those two words implies that it may not be practical or possible to avoid using substances that are toxic, and this is, if you will, the get out of jail card most chemists use to try to avoid applying this principle to their work. Let’s face it; chemists use toxic substances all the time because reactive chemicals afford reactions that are kinetically and thermodynamically favorable. And unless—and until—replacement chemicals along with new synthetic protocols are developed, inherently toxic materials will continue to be used. But it’s easier to say that it isn’t practicable and dispense with any thought about the chemical choices that are made.

It’s not that adhering to this principle is particularly difficult to do; it’s more that chemists are disinterested in doing it. For the synthetic organic chemist, effecting a successful chemical transformation in a new way or with a new molecule or in a new order is what matters. I have heard such arguments, as “all the other stuff in the flask is just there to make the transformation possible so it really doesn’t matter,” or “you have to be realistic and focus on the science.” Saying these things implies that the only science that matters is activating a carbon atom to functionalize it, or adding a ligand to a catalyst, etc., etc. This principle is asking chemists to broaden their definition of what constitutes good science.

What many have shown over and over again is that toxicity and the attendant hazard and risk associated with a chemical reaction is directly related to all the other “stuff” in a flask. In fact, the chemistry or chemical transformation in a synthesis generally impacts the overall toxicity profile (and most other measures of sustainability and green) of a product or process the least, except in those cases where we deliberately are producing a molecule that is toxic or biologically active by design. That is certainly the case for many molecules that are synthesized as in the pharmaceutical or agriculture chemical business—the molecules are toxic and/or have other effects on living organisms by design.

The chemicals and materials used in effecting chemical transformations matter and chemists need to pay more attention to the choices they make about what goes into the flask. It’s easy to discount all the other “stuff” and focus all our energy on the synthetic pathway that delivers the desired product. But when we ignore all the other “stuff,” we pay a high price and it’s a price we need to stop paying.

Occasionally, chemists do produce molecules that have toxic or other hazardous effects, and the next principle will have something to say about designing safer molecules.

• Designing Safer Chemicals

Chemical products should be designed to preserve efficacy of function while reducing toxicity.

Contributed by Nicholas D. Anastas, Ph.D., U.S. Environmental Protection Agency- New England

Minimizing toxicity, while simultaneously maintaining function and efficacy, may be one of the most challenging aspects of designing safer products and processes. Achieving this goal requires an understanding of not only chemistry but also of the principles of toxicology and environmental science. Highly reactive chemicals are often used by chemists to manufacture products because they are quite valuable at affecting molecular transformations. However, they are also more likely to react with unintended biological targets, human and ecological, resulting in unwanted adverse effects. Without understanding the fundamental structure hazard relationship, even the most skilled molecular magician enters the challenge lacking a complete toolkit.

Mastering the art and science of toxicology requires innovative approaches to chemical characterization that state that hazard is a design flaw and must be addressed at the genesis of molecular design. The intrinsic hazard of elements and molecules is a fundamental chemical property that must be characterized, evaluated and managed as part of a systems-based strategy for chemical design.

Now is the ideal time to develop a comprehensive and cooperative effort between toxicologists and chemists, focused on training the next generation of scientists to design safer chemicals in a truly holistic and trans-disciplinary manner through innovative curricular advancements. The field of toxicology is evolving rapidly, incorporating and applying the advancements made in molecular biology to reveal the mechanisms of toxicity. Elucidation of these pathways serve as the starting point for articulating design rules that are required by chemists to guide their choices in a quest to make safer chemicals. We are at the dawn of a new sunrise, poised to illuminate the path forward to a safer, healthier and more sustainable world.

More Resources and Examples

Anastas, N. Green Toxicology, 2012 in: Green Techniques for Organic Synthesis and Medicinal Chemistry , W. Zhang and B. Cue, eds., J Wiley.

Anastas, N.D. and J.C. Warner. 2005. Incorporating Hazard Reduction as a Design Criterion in Green Chemistry , Chem. Health. Safety, March/April, 3-15.

Green Chemistry Metrics: Measuring and Monitoring Sustainable Processes , 2009, A. Lapkin and D. Constable eds., J. Wiley.

Green Chemistry Education: Changing the Course of Chemistry , 2009, ACS Symposium Series 1011, P.T. Anastas, I. Levy and K.E. Parent, eds. J. Wiley

Designing Safer Chemicals , 1996, S. DeVito and R. Garrett eds., ACS Symposium Series 640.

US EPA, 2013, http://epa.gov/ncct/Tox21/ (accessed 3/3/13)

Disclaimer:

Although these references are given to provide additional information that may be useful or interesting, EPA is not responsible for, and cannot attest to the accuracy of, the content of these articles.

• Safer Solvents and Auxiliaries

The use of auxiliary substances (e.g., solvents, separation agents, etc.) should be made unnecessary wherever possible and, innocuous when used.

Dr. Concepcíon (Conchita) Jiménez-González, Director, Operational Sustainability, GlaxoSmithKline

It was a green chemistry conference and the very famous synthetic chemist had just received a question about why he had chosen a solvent that was without question a very poor choice. You have to be realistic, chemists know intuitively what's best, and solvents don't matter. It's the chemistry that counts. I've heard this kind of remark repeatedly over many years, despite the fact that it goes against the spirit and letter of Principle 5.

Solvents and mass separation agents of all kinds matter a lot to the chemistry not to mention the chemical process and the overall "greenness" of the reaction. In many cases, reactions wouldn't proceed without solvents and/or mass separation agents. To say that they don't matter, or that it's only the chemistry that counts is not just a logical fallacy, it's chemically incorrect. Solvents and separation agents provide for mass and energy transfer and without this, many reactions will not proceed.

It has also been shown that solvents account for 50 – 80 percent of the mass in a standard batch chemical operation, depending on whether you include water or you don't. Moreover, solvents account for about 75% of the cumulative life cycle environmental impacts of a standard batch chemical operation.

Solvents and mass separation agents also drive most of the energy consumption in a process. Think about it for a moment. Solvents are alternately heated, distilled, cooled, pumped, mixed, distilled under vacuum, filtered, etc. And that's before they may or may not be recycled. If they're not recycled, they are often incinerated.

Solvents are also the major contributors to the overall toxicity profile and because of that, compose the majority of the materials of concern associated with a process. On average, they contribute the greatest concern for process safety issues because they are flammable and volatile, or under the right conditions, explosive. They also generally drive workers to don personal protective equipment of one kind or another.

We will always need solvents, and with many things in chemical processes, it's a matter of impact trading. Optimize a solvent according to one green metric and many times, there are three others that don't look so good. The object is to choose solvents that make sense chemically, reduce the energy requirements, have the least toxicity, have the fewest life cycle environmental impacts and don't have major safety impacts.

Solvents and separation agents do matter and despite one or more famous synthetic organic chemists may think. It is possible to make better choices, and that is what application of this principle should promote.

Design for Energy Efficiency

Energy requirements should be recognized for their environmental and economic impacts and should be minimized. Synthetic methods should be conducted at ambient temperature and pressure.

By Dr. David Constable, Director, ACS Green Chemistry Institute ®

In recent years I've begun to talk about the green chemistry and engineering's "forgotten principles," and Design for Energy Efficiency is one of them. Amongst synthetic organic chemists, no consideration is given to temperature or pressure. The chemist just follows a protocol to get a reaction to go to completion and to separate the desired product at as high a yield as possible. Energy, from the chemist’s perspective, is irrelevant and for all intents and purposes, free. Just put the plug in the wall or the heating coil around the flask, or get the liquid nitrogen out of the dewar.

For those that do think about energy, most if not all the attention that energy gets from chemists is devoted to heating, cooling, separations, electrochemistry, pumping and reluctantly, to calculations related to thermodynamics (e.g., Gibbs Free Energy). The attention is not in minimizing or considering where energy comes from or if it matters what form is used, it's just a given that we need to heat or cool or shove electrons into the reaction to make or break bonds. In reflecting on my own training as a chemist, I never was asked to convert any heating, cooling, pumping or electrochemical requirements to a cost for electricity, steam or some other utility. That may be done in chemical engineering, but not in chemistry.

Energy is a key issue for the 21st century. A majority of the energy that is produced is based, and will continue to be based on fossil fuels. And most of the energy that is delivered to the point of use is lost in conversion and transmission. What this means is that if you look at the life cycle of energy production, and you look at how much energy is actually available for useful work at the point of need, it is less than 1 or 2 percent of the energy that was originally available in the fossil fuel. It is also true that most fossil fuel energy is used for transportation services of one kind or another and the second biggest use is in space heating and cooling. There are a tremendous number of opportunities for chemists to change this energy use profile, but it is my experience that very few chemists see themselves as being a part of either transportation or the built environment.

If you think about where most chemists are trained around energy, and certainly chemical engineers are, it's around ∆H in the Gibbs Free Energy equation. Heats of formation, heats of vaporization, enthalpy, exothermic reactions, etc; these are what we think about. The interesting thing is that nature largely works with ∆S and weak forces of interaction. You don’t see a tree doing photosynthesis at reflux using a solvent, or a cell membrane is not extruded at the melt temperature of something like polystyrene.

There is so much more to energy and engaging chemists in thinking about energy than asking them to run reactions at ambient temperature and pressure. Reactions themselves are rarely where a majority of energy is used; most is used in solvent removal to set up for the next reaction, or to remove one solvent and replace it with another, or to isolate the desired product, or to remove impurities. Apart from hydrogenations or reactions that are oxygen or moisture sensitive, most reactions are done at atmospheric pressure. This doesn't mean that energy isn't important, it is just important in areas where most chemists are not focused.

Once again, thinking about more than one part of the reaction or the process during the design of a new molecule is critical not only from the standpoint of energy, but also from many different angles. Energy—like thinking about how to arrange a synthesis to have the fewest number of steps, or use the lowest cost starting materials or any other aspect of interest to the synthetic or process chemist—is just another design parameter. Historically it has not been seen as that, but we can no longer afford to design new molecules in the absence of a detailed and extended consideration of how energy will be used.

• Use of Renewable Feedstocks

A raw material or feedstock should be renewable rather than depleting whenever technically and economically practicable.

By Dr. Richard Wool, Professor of Chemical and Biomolecular Engineering and Director of the Affordable Composites from Renewable Materials program, University of Delaware.

The concept of making all our future fuels, chemicals and materials from feedstocks that never deplete is an interesting concept which at first glance seems impracticable. Mankind currently removes fossil fuels, coal, oil and natural gas from the ground and extracts minerals for profit until they are exhausted. In particular, our fossil fuels for carbon-based chemicals and materials are being rapidly depleted in a predictable manner with the expected rise of global populations and expanding energy intensive economies on several continents. The impacts on human health and the environment are significant and present major challenges for our scientists and leaders in the next 50 years.

Can we address these global problems by using Green Chemistry Principal #7? Yes, we will get our feedstock, as if by magic, from “thin air” and it will be renewable. The carbon in the air is in the form of carbon dioxide CO 2 and methane CH 4 and is removed by photosynthetic processes powered by the sun to form plants, trees, crops, algae, etc., which collectively we call “biomass”.

Nature produces about 170 billion tons of plant biomass annually, of which we currently use about 3.5 percent for human needs. It is estimated that about 40 billion tons of biomass, or about 25 percent of the annual production, would be required to completely generate a bio-based economy. The technical challenge in the use of such renewable feedstocks is to develop low energy, non-toxic pathways to convert the biomass to useful chemicals in a manner that does not generate more carbon than is being removed from “thin air”; the difference between C(in) from the air, and C(out) from the energy used, is the carbon footprint ΔC. Ideally, when using Principal #7, all carbon footprints by design should be positive such that C(in) >> C(out). This leads in a natural way to the reduction of global warming gasses impacting our current climate change. We should also insure that the new chemicals and materials derived from renewable resources are non-toxic or injurious to human health and the biosphere.

In 2002, the U.S. Department of Energy in their Vision for Bioenergy and Bio-based Products in the United States stated:

“By 2030, a well-established, economically viable, bioenergy, and bio-based products industry is expected to create new economic opportunities for rural America [globalization through localization], protect and enhance the environment, strengthen the U.S. energy independence, provide economic security, and deliver improved products to consumers.”

In the past 10 years, significant advances have been made in the development of fuels, chemicals and materials from renewable feedstocks. These for example, have included biodiesel from plant oils and algae, bioethanol and butanol from sugars and lignocellulose, plastics, foams and thermosets from lignin and plant oils, and even electronic materials from chicken feathers. In terms of Green Chemistry Principal #7, our future is bright and laced with optimism due to the ongoing fruitful collaborations between several disciplines involving biotechnology, agronomy, toxicology, physics, engineering and others, where new fuels, chemicals and materials are being derived from renewable feedstock from “thin air” with minimal impact on human health and the environment.

Additional Resource

Vision for Bioenergy and Biobased Products in the United States - Updated 2006

• Reduce Derivatives

Unnecessary derivatization (use of blocking groups, protection/deprotection, temporary modification of physical/chemical processes) should be minimized or avoided if possible, because such steps require additional reagents and can generate waste.

By Peter J. Dunn, Green Chemistry Lead, Pfizer

One of the key principles of green chemistry is to reduce the use of derivatives and protecting groups in the synthesis of target molecules. One of the best ways of doing this is the use of enzymes. Enzymes are so specific that they can often react with one site of the molecule and leave the rest of the molecule alone and hence protecting groups are often not required.

A great example of the use of enzymes to avoid protecting groups and clean up processes is the industrial synthesis of semi-synthetic antibiotics such as ampicillin and amoxicillin.

In the first industrial synthesis Penicillin G (R=H) is first protected as its silyl ester [R = Si(Me) 3 ] then reacted with phosphorus pentachloride at -40 o C to form the chlorimidate 1 subsequent hydrolysis gives the desired 6-APA from which semi-synthetic penicillins are manufactured.

(i) TMSCl then PCl5, PhNMe2, CH2Cl2, -40oC (ii) n-BuOH, -40oC, then H2O, 0oC (iii) Pen-acylase, water

This synthesis has been largely replaced by a newer enzymatic process using pen-acylase. This synthesis occurs in water at just above room temperature. The new synthesis has many advantages from a green perspective one of which is that the silyl protecting group is not required.

More than 10,000 metric tons of 6-APA is made every year and much of it by the greener enzymatic process so this is a fantastic example of Green Chemistry making a real difference.

More Resources

The Importance of Green Chemistry in Process Research and Development

Catalytic reagents (as selective as possible) are superior to stoichiometric reagents.

Contributed by Roger A. Sheldon, Ph.D., Emeritus Professor of Biocatalysis and Organic Chemistry, Delft University of Technology and CEO of CLEA Technologies B.V.

A primary goal of green chemistry is the minimization or preferably the elimination of waste in the manufacture of chemicals and allied products: “prevention is better than cure” . This necessitates a paradigm shift in the concept of efficiency in organic synthesis, from one that is focused on chemical yield to one that assigns value to minimization of waste. What is the cause of waste? The key lies in the concept of atom economy: “synthetic methods should be designed to maximize the incorporation of all materials used in the process into the final product” . In the reaction scheme we compare, for example, the reduction of a ketone to the corresponding secondary alcohol using sodium borohydride or molecular hydrogen as the reductant. Reduction with the former has an atom economy of 81%  while reduction with the latter is 100% atom economic, that is everything ends up in the product and, in principle, there is no waste. 

Unfortunately, hydrogen does not react with ketones to any extent under normal conditions. For this, we need a catalyst such as palladium-on-charcoal. A catalyst is defined as “a substance that changes the velocity of a reaction without itself being changed in the process” . It lowers the activation energy of the reaction but in so doing it is not consumed. This means that in principle at least, it can be used in small amounts and be recycled indefinitely, that is it doesn’t generate any waste. Moreover, molecular hydrogen is also the least expensive reductant and, for this reason, catalytic hydrogenations are widely applied in the petrochemical industry, where the use of other reductants is generally not economically viable. It is only in the last two decades, however, following the emergence of green chemistry, that catalysis has been widely applied in the pharmaceutical and fine chemical industries, with the goal of minimizing the enormous amounts of waste generated by the use of stoichiometric inorganic reagents. This involves the use of the full breadth of catalysis: heterogeneous, homogeneous, organocatalysts and, more recently, Nature’s own exquisite catalysts: enzymes. The latter are particularly effective at catalyzing highly selective processes with complex substrates under mild conditions and, hence, are finding broad applications in the pharmaceutical and allied industries. Moreover, they are expected to play an important role in the transition from a chemical industry based on non-renewable fossil resources to a more sustainable bio-based economy utilizing renewable biomass as the raw material, yet another noble goal of green chemistry.

R.A. Sheldon, I. Arends and U. Hanefeld, Green Chemistry and Catalysis , Wiley-VCH, Weinheim, 2007 (ISBN 978-3-527-30715-9)

R.A. Sheldon, Fundamentals of green chemistry: efficiency in reaction design , Chem. Soc. Rev. 41 (2012) 1437-1451.

R.A. Sheldon, E Factors, green chemistry and catalysis: An odyssey Chem. Commun. (2008) 3352-3365.

• Design for Degradation

Chemical products should be designed so that at the end of their function they break down into innocuous degradation products and do not persist in the environment.

Contributed by Rich Williams, Founder and President at Environmental Science & Green Chemistry Consulting, LLC

Green chemistry practitioners aspire to optimize the commercial function of a chemical while minimizing its hazard and risk. Hazard, the capability to cause harm, is an inherent characteristic arising, like function, from a chemical’s stereochemistry (the content and arrangement of atoms). Green chemistry principles 3, 4, 5, and 12 guide designers to reduce the hazards of chemicals. Principle 10, however, guides the design of products that degrade after their commercial function in order to reduce risk or the probability of harm occurring. Risk is a function of both a molecule’s inherent hazard AND exposure – contact between a chemical and a species. Degradation can eliminate significant exposure, thereby minimizing risk regardless of the hazard of the chemical involved.

Exposure to persistent chemicals can be significant as a result of global dispersion enabled by properties such as volatility or sorption to particles and partitioning into organisms based on properties such as fat solubility. Regulators have established criteria (half-lives in water, soil, air) that define persistence within frameworks used to identify chemicals as PBT (Persistent, Bioaccumulative, Toxic).

A green chemistry objective is to design out molecular features responsible for hazardous characteristics and risk. Trade-offs, or alternative approaches, must be evaluated when the molecular features to be designed in for commercial function overlap with those to be designed out to reduce hazard and risk.

Biodegradation, hydrolysis, and photolysis can be designed into chemical products. In the same way that mechanistic toxicology knowledge is essential to identify and design out molecular features that are the basis for hazards, an understanding of the mechanisms of degradation and persistence are required to design in chemical features that promote degradation and eliminate features that promote persistence. Many persistent compounds are extensively chlorinated. Halogens such as chlorine are electron withdrawing, thereby inhibiting the enzyme systems of microbes because aerobic microbial degradation favors electron rich structures.

Prediction methods that can guide the design of molecular architecture expected to degrade include rules of thumb linking structural features to degradability or persistence, databases of existing knowledge, models that evaluate biodegradability or PBT attributes, and experimental testing. All of these tools can be adapted to individual chemical sectors and specific objectives.

Understanding the anticipated release and transport pathways for a chemical informs the selection of an effective design strategy. Degradation must occur within the relevant environmental compartment(s) and at a meaningful rate. Domestic wastewater typically passes through a vigorous bioreactor within wastewater treatment plants (WWTP). The consumer product industry has designed molecules for removal within these bioreactors. In the early 1960’s, industry transitioned from non-biodegradable branched surfactants, which caused extensive foaming and other health problems in surface waters receiving WWTP effluent, to biodegradable linear alkyl benzene sulfonate based detergents – an approach to innovative design that continues today.

Tools currently exist to enable the implementation of principle 10, but advances in mechanistic understandings linking molecular features to hazards and degradability will enable more comprehensive application of green chemistry to control hazard and risk. Effective communication across disciplines is also essential to provide designers with knowledge they can factor into the complexities of product design. Because of regulatory and business constraints, many product design decisions must be made relatively early. Predictive decision-making tools must provide confidence about hazard and risk in a way that is aligned with the timing and magnitude of development decisions, and most importantly, while there is still flexibility to alter a molecular design or product formulation.

• Real-time analysis for Pollution Prevention

Analytical methodologies need to be further developed to allow for real-time, in-process monitoring and control prior to the formation of hazardous substances.

Contributed by Douglas Raynie, Assistant Professor, Chemistry & Biochemistry, South Dakota State University

Imagine driving down a busy highway in a car with all of the windows painted an opaque black!!! While that scenario many not seem realistic (or safe), what if you had a 360° camera and the sensors and technology being developed for self-driving cars? Now, the safety of your commute is more ensured.

This description, while applied to automobiles, is illustrative of the 11th principle of green chemistry. Just as we need real-time feedback for driving safety, real-time feedback is essential in proper functioning chemical processes. Most chemists are familiar with laboratory analysis from their undergraduate training. But analysis can also be performed in-line, on-line, or at-line in a chemical plant, a subdiscipline known as process analytical chemistry. Such analysis can detect changes in process temperature or pH prior to a reaction going out of control, poisoning of catalysts can be determined, and other deleterious events can be detected before a major incident occurs.

Process analysis is of such importance that the US Food and Drug Administration encourages such an approach for the manufacture, design, and control of pharmaceutical manufacturing. Since 1984, an industry-academic partnership, the Center for Process Analytical Chemistry, has promoted research into emerging techniques for process analytical chemistry.

While the traditional roles of analytical chemistry also advance green chemistry goals, the effective application of process analytical chemistry directly contributes to the safe and efficient operation of chemical plants worldwide.

Additional resource:

Center for Process Analysis & Control

• Inherently Safer Chemistry for Accident Prevention

Substances and the form of a substance used in a chemical process should be chosen to minimize the potential for chemical accidents, including releases, explosions, and fires.

Contributed by Shelly Bradley, Campus Chemical Compliance Director, Hendrix College; Dr. David C. Finster, Professor of Chemistry, Wittenberg University; and Dr. Tom Goodwin, Elbert L. Fausett Professor of Chemistry, Hendrix College

Safety can be defined as the control of recognized hazards to achieve an acceptable level of risk. Green Chemistry Principle # 12 is known as the “Safety Principle”. It may be the most overlooked of the twelve principles, yet it is the logical outcome of many of the other principles. In fact, it is practically impossible to achieve the goals of Principle 12 without the implementation of at least one of the others. Since the very essence of green chemistry is to “… reduce or eliminate the use or generation of hazardous substances” there is an intrinsic connection to laboratory safety. While there are a few exceptions, the majority of the Green Chemistry Principles will result in a scenario that is also safer.

Under the umbrella of the Environmental Protection Agency (EPA), Green Chemistry’s primary focus is clearly to make the environment safer. Materials and processes that are safer for the environment also are likely to be safer for the general public. However, another population that benefits from green chemistry and is not often mentioned is workers. The manufacturing or laboratory worker is often the first in-line person to benefit from hazard reductions.

The health and safety of workers are under the purview of the Occupational Safety and Health Administration (OSHA). In a recent news release, OSHA unveiled a chemical management system designed to increase worker safety. The Hierarchy of Safety Controls as highlighted in OSHA’s new Transitioning to Safer Chemicals Toolkit illustrates the difference between focusing on the control or hazard part of the safety definition. Traditional chemical safety models focus primarily on the control component of that definition. The graphic (adapted from OSHA) shows that the most effective means of increasing safety is eliminating the hazard component. Since the elimination of hazards is the basic tenet of Green Chemistry, this marriage of the ideas of Green Chemistry from both OSHA and EPA should have a synergistic impact on hazard reduction. Combining the forces of these two agencies toward a common goal may lead to conversations and changes that result in safer conditions for workers, a safer environment for the general public, and a safer planet for us all.

References Cited:

Manuele, F. A. Acceptable Risk , Professional Safety , 2010 , 30-38 (accessed 11/22/2013)

Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice ; Oxford University Press; New York, 1998.

US OSHA, OSHA releases new resources to better protect workers from hazardous chemicals , (accessed 11/22/2013)

US OSHA, Transitioning to Safer Chemicals: A Toolkit for Employers and Workers , (accessed 11/22/2013)

US OSHA,  Why Transition to Safer Alternatives? , (accessed 11/22/2013)

*Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice, Oxford University Press: New York, 1998, p.30. By permission of Oxford University Press.

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Introduction to Green Chemistry

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Introduction to Green Chemistry. Mary Kirchhoff Associated Colleges of the Chicago Area 16 September 2003. Green Chemistry. Green Chemistry is the design of chemical products and processes that reduce or eliminate the use and/or generation of hazardous substances.

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Introduction to Green Chemistry Mary Kirchhoff Associated Colleges of the Chicago Area 16 September 2003

Green Chemistry • Green Chemistry is the design of chemical products and processes that reduce or eliminate the use and/or generation of hazardous substances.

Historical Approach to Environmental Problems • Waste treatment, control, and disposal; pollutant monitoring; hazardous waste site cleanup. • Development of standards for emissions to air, releases to water, and disposal by land, as well as regulation of these standards. • “Command and Control”

Growth in Environmental Regulation EPACT FFCA CERFA CRAA PPA PPVA IEREA ANTPA GLCPA ABA CZARA WRDA EDP OPA RECA CAAA GCRA GLFWRA HMTUSA NEEA AMFA ARPAA AJA ASBCAA ESAA-AECA FFRAA FEAPRA IRA NWPAA CODRA/NMSPAA FCRPA MMPAA 120 110 100 90 80 70 60 50 40 30 20 10 0 AQA NAWCA RCRAA WLDI APA SWDA CERCLA CZMIA COWLDA FWLCA MPRSAA WQA SDWAA SARA NWPA BLRA ERDDAA EAWA NOPPA PTSA UMTRCA ESAA QGA NCPA CAAA CWA SMCRA SWRCA SDWAA ARPA MPRSAA Number of Laws BLBA FWPCA MPRSA CZMA NCA FEPCA PWSA MMPA HMTA TSCA FLPMA RCRA NFMA CZMAA ESA TAPA FRRRPA SOWA DPA NEPA EQIA CAA EPA EEA OSHA FAWRAA NPAA AQA FOIA FCMHSA WRPA AFCA FHSA NFMUA WSRA EA RCFHSA TA FWCA BPA FIFRA AEPA PAA NHPA WLDA WA FWCAA NBRA MBCA NPS FAWRA FWA IA AEA AA RHA NLRA WPA YA 1870 1880 1890 1900 1910 1920 1930 1940 1950 1960 1970 1980 1990 2000

Environmental Expenditures& Economic SustainabilitySource: R. R. Bezdek., MISI - 1999

Pollution Prevention Act of 1990 PollutionPrevention SourceReduction Recycling Treatment Disposal

Characterization of Environmental Problems Risk = f(hazard x exposure) Traditionally, risk management has focused on exposure rather than hazard.

Circumstantial vs. Intrinsic Recognize hazard as a design flaw • Circumstantial • Use • Exposure • Handling • Treatment • Protection • Recycling • Costly • Intrinsic • Molecular design for reduced toxicity • Reduced ability to manifest hazard • Inherent safety from accidents or terrorism • Increased potential profitability

Why Green Chemistry? • “Business is going to get significantly more profitable through the application of green technology. Proactive companies are finding the theme ‘good for business’ to be credible and real.” Paul V. Tebo, Vice President for Safety, Health, and Environment, DuPont • We have found that voluntary environmental improvements - as encouraged by programs like EPA’s Green Chemistry Challenge ... - can return as much as 53% on capital, compared with a negative 16% when improvements are mandated by law.” William S. Stavropoulos, President and Chief Executive Officer, The Dow Chemical Company

Presidential Green Chemistry Challenge • Goal: To promote pollution prevention and industrial ecology through a new EPA Design for the Environment partnership with the chemical industry. • Challenge: To find cleaner, cheaper, and smarter ways to manufacture the products that we depend on.

Presidential Green Chemistry Challenge Awards • Alternative synthetic pathways • Alternative reaction conditions • Designing safer chemicals • Academic • Small business

Twelve Principles of Green Chemistry • 1. Prevention • 2. Atom Economy • 3. Less Hazardous Chemical Syntheses • 4. Designing Safer Chemicals • 5. Safer Solvents and Auxiliaries • 6. Design for Energy Efficiency • 7. Use of Renewable Feedstocks • 8. Reduce Derivatives • 9. Catalysis • 10. Design for Degradation • 11. Real-time Analysis for Pollution Prevention • 12. Inherently Safer Chemistry for Accident Prevention

Principle 1It is better to prevent waste than to treat or clean up waste after it is formed.

Redesign of the Sertraline Process • Sertraline: active ingredient in Zoloft • Combined process • Doubled yield • Ethanol replaced CH2Cl2, THF, toluene, and hexane • Eliminated use of 140 metric tons/year TiCl4 • Eliminated 150 metric tons/year 35% HCl Pfizer

Redesign of the Sertraline Process

Principle 1: Waste prevention • Cytovene • antiviral agent used in the treatment of cytomegalovirus (CMV) retinitis infections • AIDS and solid-tissue transplant patients • Improved synthesis • reduced chemical processing steps from 6 to 2 • reduced number of reagents and intermediates from 22 to 11 • eliminated 1.12 million kg/year liquid waste • eliminated 25,300 kg/year solid waste • increased overall yield by 25%

Principle 2Synthetic methods should be designed to maximize the incorporation of all materials used into the final product.

Principle 2: Atom economy • Traditional synthesis of ibuprofen • 6 stoichiometric steps • <40% atom utilization

Principle 2: Atom economy • Catalytic synthesis of ibuprofen • 3 catalytic steps • 80% atom utilization (99% with recovered acetic acid) BHC

Principle 3Wherever practicable, synthetic methodologies should be designed to use and generate substances that possess little or no toxicity to human health and the environment.

Principle 3: Non-toxic substances • Disadvantages • phosgene is toxic, corrosive • requires large amount of CH2Cl2 • polycarbonate contaminated with Cl impurities

Principle 3: Non-toxic substances • Advantages • diphenylcarbonate synthesized without phosgene • eliminates use of CH2Cl2 • higher-quality polycarbonates • Komiya et al., Asahi Chemical Industry Co.

Alternative Synthetic Pathways • Sodium iminodisuccinate • Biodegradable, environmentally friendly chelating agent • Synthesized in a waste-free process • Eliminates use of hydrogen cyanide Bayer Corporation and Bayer AG 2001 Alternative Synthetic Pathways Award Winner

Principle 4Chemical products should be designed to preserve efficacy of function while reducing toxicity.

Principle 4: Reduce Toxicity • Spinosad: a natural product for insect control • produced by Saccharopolyspora spinosa • isolated from Caribbean soil sample • demonstrates high selectivity, low toxicity Dow AgroSciences

Designing Safer Chemicals • Cationic electrodeposition coatings containing yttrium • Provides corrosion resistance to automobiles • Replaces lead in electrocoat primers • Less toxic than lead and twice as effective on a weight basis PPG Industries 2001 Designing Safer Chemicals Award Winner

Small Business Award • PYROCOOL Technologies, Inc. • PYROCOOL F.E.F. (Fire Extinguishing Foam) • 0.4% aqueous mixture of highly biodegradable nonionic surfactants, anionic surfactants, and amphoteric surfactants • replacement for halon gases and aqueous film forming foams (AFFFs)

ACQ Wood Preservatives • Pressure-treated lumber • 7 million board feet/year • chromated copper arsenate (CCA) preservative • 40 million pounds of arsenic • 64 million pounds of hexavalent chromium • Alkaline Copper Quaternary (ACQ) wood preservative • Bivalent copper complex plus quaternary ammonium compound dissolved in ethanolamine of ammonia • Virtually eliminates use of arsenic in US • Avoids production, transportation, use, and disposal risks associated with CCA Chemical Specialties, Inc.

Principle 5The use of auxiliary substances (e.g. solvents, separation agents, etc.) should be made unnecessary wherever possible and, innocuous when used.

Principle 5: Benign solvents • Carbon-carbon bond formation in water • Diels-Alder, Barbier-Grignard, pericyclic • Indium-mediated cyclopentanoid formation Li, Tulane University

Research to Commercialization: Thomas Swan & Co Ltd • Multi-purpose plant using supercritical fluids • First full-scale facility for continuous, multi-purpose synthesis, including • Hydrogenations • Friedel-Crafts reactions • Hydroformylations • Etherifications • Technology developed with the University of Nottingham

Reactions in Supercritical Fluids • Formation of cyclic ethers • Hydrogenation Poliakoff, University of Nottingham

CO2 for Dry Cleaning • Dry Cleaning • current process uses perc (perchloroethylene), a suspected carcinogen and groundwater contaminant • new process uses liquid carbon dioxide, a nonflammable, nontoxic, and renewable substance

Non-Fluorous CO2-Philic Materials • Replacement for expensive, persistent fluorous CO2-philes • New CO2-philes needed to expand commercial applications of CO2 • Poly(ether-carbonates) • Lower miscibility pressures than perfluoropolyethers • Biodegradable • 100 times less expensive Beckman, University of Pittsburgh

Principle 6Energy requirements should be recognized for their environmental and economic impacts and should be minimized. Synthetic methods should be conducted at ambient temperature and pressure.

Principle 6: Minimize energy usage • Catalytic synthesis of ULTEM® thermoplastic resin • 25% less energy required to produce each pound of resin • volume of organic waste stream for off-site disposal decreased by 90% • 50% less catalyst used GE Plastics (General Electric Corporation)

Alternative products • Thermal Polyaspartic Acid (TPA) • catalytic polymerization process • biodegradable polymer • substitute for non-biodegradable polyacrylic acid (PAC) • Donlar Corporation

Principle 7A raw material of feedstock should be renewable rather than depleting wherever technically and economically practicable.

Adipic Acid Synthesis • Contributes 2% anthropogenic N2O/year

Adipic Acid Synthesis • Recycles nitrous oxide into adipic acid synthesis • new pathway to phenol Solutia, Inc.

Adipic Acid Synthesis • No nitrous oxide generated • Renewable feedstock replaces petroleum-based feedstock Draths and Frost, Michigan State

Principle 7: Renewable feedstocks • Conversion of waste biomass to levulinic acid • paper mill sludge, municipal solid waste, unrecyclable waste paper, agricultural residues Biofine, Incorporated

Principle 7: Renewable feedstocks • CO2 feedstock in polycarbonate synthesis • Improved Zn catalyst yields faster reaction, uses milder reaction conditions • Coates et al., Cornell University

Principle 8Unnecessary derivatization (blocking group, protection/deprotection, temporary modification of physical/chemical processes) should be avoided whenever possible.

Boric Acid-Mediated Amidation • Direct amidation of carboxylic acids with amines • Boric acid: nontoxic, safe, inexpensive • Eliminates use of SOCl2, PCl3, phosgene • Widely applicable Emisphere Technologies, Inc

Principle 8: Derivatization • Enzymatic synthesis of cephalexin • eliminates protection/deprotection of functional groups

Principle 9Catalytic reagents (as selective as possible) are superior to stoichiometric reagents.

Principle 9: Catalysis • Improved synthesis of a central nervous system compound • interdisciplinary approach, combining chemistry, microbiology, and engineering • For every 100 kg product, • 300 kg chromium waste eliminated • 34,000 liters solvent eliminated Eli Lilly and Company

Principle 9: Catalysis

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Green Chemistry

Green Chemistry. Sponsored by:. “ Chemistry has an important role to play in achieving a sustainable civilization on earth.” — Dr. Terry Collins, Professor of Chemistry Carnegie Mellon University. Definition.

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Green Chemistry. GREEN CHEMISTRY. DEFINITION Green Chemistry is the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products . GREEN CHEMISTRY IS ABOUT

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Green Chemistry. By Dr. Kandikere Ramaiah Prabhu Principal Research Scientist Department of Organic Chemistry Indian Institute of Science Bangalore – 560 012. October 23, 2010, Bangalore. History….. Green Chemistry is born around 199o What is green chemistry or Sustainable Technology

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Green Chemistry . By Emmie Guy 10 Orange. What is meant by the term green chemistry?. The term Green Chemistry relates to creating new products, chemicals and procedures to have a positive impact on our environment in order to take care of the world we live in by preventing pollution.

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Green Chemistry. Rhiannon Bennett. Green Chemistry follows a set of 12 Principles in order to avoid the use or generation of hazardous substances. It is used in industrial production to prevent pollution and to minimise effect on the environment. What is green chemistry?.

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Green Chemistry. By Akrem Abdul. What is Green Chemistry?.

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Green Chemistry. By Jeremy Dolphin. What is Green Chemistry?. Green chemistry is a branch of chemistry that focuses on more environmentally safe production and use of chemicals and reactions. . The twelve principles of green chemistry.

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Green Chemistry. Daniel van der Linden. Green Chemistry. 1. Explain what is meant by the concept of “ Green Chemistry ”? Green Chemistry is designing chemical products that reduce eliminate and hazardous substances. Therefore causing less damage to environment and humans.

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GREEN CHEMISTRY. What is it? • encourages environmentally conscious behaviour • reduces and prevents pollution • reduces the destruction of the planet. GREEN CHEMISTRY. What is it? • encourages environmentally conscious behaviour • reduces and prevents pollution

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Green Chemistry. Milan Sanader Author, Nelson Chemistry. GREEN CHEMISTRY INVOLVES…. Reducing or eliminating the use or production of hazardous substances in the manufacture of chemical products Considering the hazards of reagents as well as their properties. A GREEN CHEMICAL PROCESS IS.

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Green Chemistry. By Courtney Smith 10 Orange. What Is Green Chemistry??. Green chemistry is a design and process of safer chemicals to eliminate the use of hazardous substances. Green chemistry relies on 12 principles that are used to re-design or design molecules. 12 Principles.

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Green Chemistry: Introduction and Applications

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Green Chemistry

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