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Annual Report 2010

Systems

Policy & Outreach

Education

% FAME (scCO2)

Energy

Water

100% 90% 80% 70% 60% 50% 40% 30% 20% 10% 0% 50 70 90 Pressure, psi (isotherm 80C) Temperature, C (isobar 6000 psi)

C24:0 C22:0 C22:1 C20:0 C18:0 C18:1 C18:2 C18:3 C18:4 C16:0 C16:1 C16:3 C16:4 C14:0 C12:0

Materials

Center for Green Chemistry & Green Engineering at Yale


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Letter from the Director The Center’s third year of operation was an exciting one. We continued to build up our staff and infrastructure, had our most successful year in publishing papers in the highest quality peer-reviewed journals, and established several new research areas and collaborations. Our senior staff was successful in securing grant funding for a number of key projects. Furthermore, it is testimony to the talent and commitment of our students that they were recipients of prestigious fellowships from the National Science Foundation and the US Environmental Protection Agency. We are also proud that one of our PhD candidates was an inventor on the Center’s first US patent application. 2010 was also enormously successful in terms of the Center’s outreach efforts. Our new website launched early in the year and has been very popular bringing us new contacts and potential partners for future research and education projects. Our staff and students traveled worldwide to premier green chemistry and green engineering conferences, increasing the Center’s visibility as a source of cutting-edge research results, educational materials, and policy analysis. We continued to strive for a transdisciplinary, integrated working environment and you will find that reflected in this annual report. Our fundamental research broadly falls into the categories of materials, energy, systems, and water. The tremendous success of these projects depends on staff and students from a wide variety of backgrounds working side-by-side: not only chemists and engineers but also microbiologists, industrial ecologists, geographers, and political scientists. The growing successes in research have been simultaneous with new curriculum design and outreach to both academe and the general public. It is this combination of deep expertise with broad perspective that has been critical to the Center’s success to date and as we go forward. We are looking forward to building on last year’s success as we continue to make progress towards a more sustainable future through green science and technology. I invite you to visit our website (www. greenchemistry.yale.edu) where you can find more details on our latest activities. You can also follow us via Twitter at @YaleGCGE. As always, do not hesitate to get in touch with us at greenchemistry@yale.edu. We look forward to connecting with you. Sincerely,

Julie B. Zimmerman Acting Director Assistant Director, Research Center for Green Chemistry & Green Engineering at Yale


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Managing Directors Paul Anastas, PhD Director, Currently on Public Service Leave with the US EPA Teresa and H. John Heinz III Professor in the Practice of Chemistry for the Environment

Dr. Anastas has been appointed by President Barack Obama to serve as the Science Advisor and Assistant Administrator for Research and Development for the US EPA. Dr. Anastas is the Teresa and H. John Heinz III Professor in the Practice of Chemistry for the Environment. He is the Professor in the Practice of Green Chemistry with appointments in the School of Forestry and Environmental Studies, Department of Chemistry, and Department of Chemical Engineering. In addition, Dr. Anastas serves as the Director of the Center for Green Chemistry and Green Engineering at Yale. From 2004 -2006, Paul Anastas served as Director of the Green Chemistry Institute in Washington, D.C. He was previously the Assistant Director for the Environment in the White House Office of Science and Technology Policy where he worked from 1999-2004. Trained as a synthetic organic chemist, Dr. Anastas received his Ph.D. from Brandeis University and worked as an industrial consultant. He is credited with establishing the field of green chemistry during his time working for the U.S. Environmental Protection Agency as the Chief of the Industrial Chemistry Branch and as the Director of the U.S. Green Chemistry Program. Dr. Anastas has published widely on topics of science through sustainability, such as the books Benign by Design, Designing Safer Polymers, Green Engineering, and his seminal work with co-author John Warner, Green Chemistry: Theory and Practice.

Julie B. Zimmerman, PhD Acting Director Assistant Professor of Green Engineering School of Engineering and Applied Sciences School of Forestry and Environmental Studies

Dr. Julie Beth Zimmerman is an Assistant Professor of Green Engineering jointly appointed in the School of Engineering and Applied Science (Environmental Engineering Program) and the School of Forestry and Environment at Yale University.  Dr. Zimmerman also serves as the Acting Director of the Center for Green Chemistry and Green Engineering at Yale. Her research interests include green chemistry and engineering, systems dynamics modeling of natural and engineered water systems, environmentally benign design and manufacturing, the fate and impacts of anthropogenic compounds in the environment as well as appropriate water treatment technologies for the developing world. She also conducts research on corporate environmental behavior and governance interventions to enhance the integration of sustainability in industry and academia.  Dr. Zimmerman previously served as an Engineer in the Office of Research and Development at the United States Environmental Protection Agency where she managed grants to academia and small businesses in the areas of pollution prevention and sustainability.  She received a joint PhD from the University of Michigan in Environmental Engineering and Natural Resource Policy.

Evan Beach, PhD Program Manager Associate Research Scientist

Dr. Evan Beach is a research scientist in the Department of Chemistry. He joined the Anastas group in 2007 after working in green chemistry laboratories at Carnegie Mellon University and The University of North Carolina at Chapel Hill. His research interests are focused on transformations of biomass, including exploitation of lignin and algae biomass as sources of value-added chemicals to support biofuel technologies. Dr. Beach also develops curriculum for green chemistry and green engineering educational programs aimed at university students as well as outreach programs for the general public.


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Center Members Administrative Staff:

PhD Students:

Erin McBurney Senior Administrative Assistant

Kathryn Dana PhD Candidate, Environmental Engineering

Janice Mitchell Administrative Assistant

Patrick Foley PhD Candidate, Environmental Engineering

Research Staff:

Lauren Martini PhD Candidate, Chemistry

Katalin Barta, PhD Postdoctoral Associate Laura Brentner, PhD Postdoctoral Associate Zheng Cui, PhD Postdoctoral Associate Matthew Eckelman, PhD Postdoctoral Associate Valerie Fuchs, PhD Postdoctoral Associate

Sarah Miller PhD Candidate, Environmental Engineering Leanne Pasquini PhD Candidate, Environmental Engineering Lindsay Soh PhD Candidate, Environmental Engineering Jamila Saifee Yamani PhD Candidate, Environmental Engineering Masters Students:

Fuzhan Nasiri, PhD Assocoiate Research Scientist

Erik Fyfe Master’s Candidate, Environmental Science

Toby Sommer, PhD Associate Research Scientist

Troy Savage Master’s Candidate, Environmental Management

Adelina Voutchkova, PhD Postdoctoral Associate

Undergraduate Students:

Ranran Wang Postgraduate Associate

Megan Altizer Yale College ‘12

Visiting Researchers:

Bezawit Getachew Yale College ‘12

Thomas Sondergaard Hansen PhD Candidate, Technical University of Denmark

Brent Muller Yale College ‘11

Anthony Phimphachanh Undergraduate, National School of Chemistry, Physics, and Biology, Paris

Matthew Spaulding Yale College ‘12

Arnaud Yvon Undergraduate, National School of Chemistry, Physics, and Biology, Paris

Justin Steinfeld Yale College ‘11 Becca Santee Trietch Yale College ‘13 Shirlee Wohl Yale College ‘13


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The Center Welcomes New Research Staff Katalin Barta, PhD Postdoctoral Associate, Department of Chemistry Dr. Barta was a postdoctoral researcher in the lab of Peter Ford at UC-Santa Barbara before joining our staff at Yale in 2010. She received her Diploma in Chemistry from Eötvös Lorand University and her Ph.D. in Chemistry from RWTHAachen. She previously carried out graduate research in green chemistry, homogenous catalysis and ligand design under the direction of Professor Walter Leitner. Her master’s research focused on using alternative solvents such as fluorous biphase systems and supercritical carbon-dioxide under the supervision of Professor Istvan Horvath. Her current interest focuses on catalytic transformations of biomass. Valerie J. Fuchs, PhD Postdoctoral Environmental Research Associate Yale Institute for Biospheric Studies; Department of Chemical and Environmental Engineering Valerie studied technologies and policies related to sustainable water and wastewater treatment in the Sustainable Futures Institute at Michigan Tech.  With the Yale Institute for Biospheric Studies and the Center for Green Chemistry and Green Engineering, she is providing expertise on anthropogenic water and nitrogen cycling to: 1) build decision support systems for green and grey infrastructure design and management; 2) understand and assign real costs to water markets based on nutrient cycling and treatment using system dynamics modeling; 3) increase infrastructure sustainability through applying resilience measures; and 4) improve the future of municipal wastewater as a resource for biofuel and bioplastics systems as well as fertilizer and soil amendments through nutrient recovery. Thomas Hansen PhD Candidate, Technical University of Denmark Visiting Assistant in Research, Yale School of Engineering and Applied Science Thomas S. Hansen is a third year graduate student from Denmark. His PhD work in Denmark has mainly been focused on catalytic ways to convert biomass into useful polymer building blocks. During his time at Yale he plans to expand the principles of catalytic biomass conversion from Denmark to include other feedstocks and products directed toward a new chemical infrastructure based on biomass. He received his BSc degree in 2006 and MSc in 2008 from the University of Southern Denmark in Chemistry – Biochemistry and Molecular Biology. In 2007 he spent half a year during his master thesis working with Professor Sir J. Fraser Stoddart at UCLA in the field of supramolecular chemistry. He initiated his PhD in 2008 at the Technical University of Denmark and arrived late fall 2010 at Yale University where he will spend six months before graduating in Denmark. Thomas is working on the conversion of lignin into useful chemicals at Yale University.


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Overview of the Center The Mission of The Center for Green Chemistry and Green Engineering at Yale is to advance sustainability by catalyzing the effectiveness of the Green Chemistry and Green Engineering community. Green Chemistry and Green Engineering represent the fundamental building blocks of sustainability. Working in these disciplines, chemists and engineers are creating the scientific and technological breakthroughs that will be crucial to the future success of the human economy. The Center for Green Chemistry and Green Engineering at Yale works to stimulate and accelerate these advances. The Center is Guided By Four Core Operating Principles... • Insist on scientific and technical excellence and rigor. • Focus on generating solutions rather than characterizing problems. • Work with a diverse group of stakeholders. • Share information and perspectives broadly. We Seek To Accomplish Four Key Objectives... • Advance the science. • Prepare the next generation. • Catalyze implementation. • Raise awareness. The Focus Areas for the Center for Green Chemistry and Green Engineering Include: Research The Yale Center supports and advances research in Green Chemistry and Green Engineering (GC&GE), a critical component to building the community, designing and discovering innovative solutions, and achieving a sustainable future. The Center serves as a catalyst to both Yale and the greater Green Chemistry and Green Engineering communities for discipline-specific and cross-disciplinary research collaborations focused on key areas of GC&GE within science, technology, and policy for sustainability. Policy and Outreach The Center engages in policy, communication, and outreach initiatives that raise awareness of- and support for GC&GE. In this dialogue the Center engages with a wide network of stakeholders, including NGOs, industry, academia, and government, as well as local communities and the general public. Education A robust educational program is an essential element of the Center. Center activities are focused on educating undergraduate and graduate students in the principles and practice of GC&GE. The Center also serves the wider academic community by providing opportunities for faculty training and by developing and disseminating GC&GE curriculum materials. International Partnerships GC&GE are rapidly spreading through both industrialized nations and the emerging economies. In all regions, the Center engages with the network of scientists, engineers, policy-makers, business people, and public health and environmental experts focused on sustainability science on behalf of the greater good. Industrial Collaborations GC&GE can only provide meaningful impact on the challenges of global sustainability when implemented on a large scale. For this reason, collaboration with industry is a key part of the Yale Center’s work. Direct engagement creates a dialogue that informs industry of the latest research breakthroughs in the field of sustainable science and technology. Likewise, such engagement informs academic researchers on industry’s most important concerns. This dialogue facilitates a direct line for implementation of these innovations.


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Research: Materials Designing Safer Chemicals This project aims to derive empirical rules that can be used by chemists and engineers to guide the design of chemicals with reduced toxicological, environmental, physical and global hazards. In 2010 the Center built a custom database of toxicological data and began developing a public web interface. Center researchers devised a rapid, multi-step method for converting the chemical registry information found in the toxicity databases into 3-dimensional molecular structures suitable for property prediction with Yale-developed “Qikprop” software. The predictions of chemical reactivity have been shown to be crucial for understanding statistical correlations between molecular properties and toxicity. The first publication demonstrating the feasibility of the statistical approach appeared in the January 30th issue of Tetrahedron. It used data from EPA’s Toxic Release Inventory to show that highly toxic chemicals have distinct properties compared to chemicals in general (as taken from a database of 13 million commercial chemicals). 3D visualizations, partitioning analysis, and clustering techniques have proven to be useful for visually highlighting the property limits that are most likely to contain safe chemicals. Publications: Voutchkova, A. M.; Osimitz, T. G.; Anastas, P. T., Toward a Comprehensive Molecular Design Framework for Reduced Hazard. Chemical Reviews 2010, 110 (10), 5845-5882. Voutchkova, A. M.; Ferris, L. A.; Zimmerman, J. B.; Anastas, P. T., Towards Molecular Design for Hazard Reduction Fundamental Relationships Between Chemical Properties and Toxicity. Tetrahedron 2010, 66 (5), 1031-1039. Conference Presentations: “Towards molecular design for hazard reduction: Deriving fundamental relationships between chemical properties and toxicity,”  Adelina Voutchkova, Jakub Kostal, John Emerson, Julie B. Zimmerman, Thomas Osimitz,  Paul T. Anastas, 49th Annual Society of Toxicology Meeting, Salt Lake City, UT 14th Annual Green Chemistry and Engineering Conference, Washington D.C. Grants: Kendeda Fund: Rational Design of Safer Chemicals, 2010-2012

Non-covalent Polymer Chemistry Reversible binding between a surfactant and a homopolymer having complementary sites for the surfactant can lead to phase separation and block copolymer-like morphology.  The surfactant is designed such that specific environmental stimuli can induce changes in the polymer chain-level structure.  The “synthesis” of functional materials by guided selfassembly is in accordance with Green Chemistry principles such as solvent-free chemistry and reduced dependence on unnecessary derivatization. Publications: Gopinadhan, M.; Beach, E. S.; Anastas, P. T.; Osuji, C., Smectic Demixing in the Phase Behavior and Self-Assembly of a Hydrogen-Bonded Polymer with Mesogenic Side Chains. Macromolecules 2010, 43 (16), 6646-6654.


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Research: Materials Algae-derived Surfactants This project aims to synthesize and characterize two new classes of C-glycoside surfactants derived from algal biomass. Carbohydrate-based surfactants have long been of interest due to their desirable performance properties and their potential to be derived from renewable feedstocks. Although most carbohydrate based surfactants utilize an O-glycosidic linkage, recent advances in carbohydrate C-C bond formation allows for the facile synthesis of new classes of carbohydrate-based surfactants based on a C-glycosidic linkage. This project aims to synthesize and characterize two new classes of C-glycoside surfactants derived from algal biomass. Publications: Foley, P. M.; Phimphachanh, A.; Beach, E. S.; Zimmerman, J. B.; Anastas, P. T., Linear and Cyclic C-Glycosides as Surfactants. Green Chemistry 2010, in press, DOI:10.1039/C0GC00407C. Conference Presentations: “Pursuing Useful, Biologically Derived Small Molecules: C-Glycosides as Surface Active Agents,” Patrick Foley, Julie B. Zimmerman 14th Annual Green Chemistry and Engineering Conference, Washington D.C. Intellectual Property: The Center’s C-glycoside surfactant technology shows great promise for a variety of applications and is currently being developed in cooperation with the Office of Cooperative Research at Yale. In addition to the recent article in Green Chemistry, an International Patent Application has been filed (No. PCT/US10/55831).

Catalytic Transformation of Biomass The Center is developing new catalysts and methods for rational transformation of lignin and other biomass-derived materials. Non-food biomass is a significant, carbon-neutral energy source. Thus developing chemical approaches for its transformation either to liquid transportation fuels or to diverse useful chemicals would have significant economic and environmental benefits.  This is a challenging task due to the highly complex structure of biomass therefore many different directions will be explored during the course of this project.  Initially heterogenous catalytic systems will be studied and established. Based on these systems, we will gain insight to understanding key factors and structural features required for reactivity and selectivity that will lead to development of homogenous catalysts. These novel homogenous systems would then allow for milder reaction conditions and increased selectivity. Grants: U.S. Department of Agriculture: Transformation of Lignin into Building Blocks for Protective Coatings, 2010-2012


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Research: Materials One-pot, Multicomponent Synthesis of Arylnaphthalene Lactone Natural Products This research involves the development of a one-pot, multi-component synthesis of arylnaphthalene naural products through use of a silver catalyst and carbon dioxide. Publications: Foley, P. M.; Eghbali, E; Anastas, P. T., Silver-Catalyzed One-Pot Synthesis of Arylnaphthalene Lactone Natural Product. Journal of Natural Products 2010, 73 (5), 811-813. Foley, P.; Eghbali, N.; Anastas, P. T., Advances in the methodology of a multicomponent synthesis of arylnaphthalene lactones. Green Chemistry 2010, 12, 888-892.

Physicochemical Characterization and Toxicity Evaluation of Functionalized Single Walled Carbon Nanotubes (SWCNTs) The objective of this research is to determine whether surface functionalizations decrease both environmental and human toxicity of single-wall carbon nanotubes (SWCNTs)Several surface functionalities will be studied. Conference Presentations: “Exploring the environmental and human health implications of single walled carbon nanotubes (SWNTs): A comparative bacterial toxicity study of pristine, hydroxy, and carboxy functionalized SWNTs,” Leanne Pasquini, Julie B. Zimmerman 14th Annual Green Chemistry and Engineering Conference, Washington D.C. Grant: National Science Foundation: Design of Safer Carbon-Based Nanomaterials: The Impact of Surface Modifications on Toxicity and Environmental Fate and Transport, 2009-2012 Fellowships awarded to Leanne Pasquini: National Science Foundation’s Graduate Research Fellowship US EPA STAR Fellowship

Polymers from Triglycerides This work focuses on replacements for styrene comonomer in plant oil-based thermoset polymers. It is possible to use bio-based comonomers with modified soybean oil to create crosslinked materials. Mechanical testing is underway.


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Research: Energy Biodiesel From Algae in Uganda This project is investigating algae strains obtained from salt lakes in Uganda for their potential in biodiesel production. Lake Katwe in Uganda is home to a number of unidentified algae species that grow there in abundance.  By determining the species and collecting information about their lipid content, this project will help identify the prospects for algae as a source of fuel and chemicals in East Africa, complementing “second generation” oilseed crops as a feedstock for an integrated biorefinery. Publications: Klein, A. P.; Beach, E. S.; Emerson, J. W.; Zimmerman, J. B., Accelerated Solvent Extraction of Lignin from Aleurites moluccana (Candlenut) Nutshells. Journal of Agricultural and Food Chemistry 2010, 58 (18), 10045-10048.

Biohydrogen Production in Reverse Micelles Understanding why fermentative bacterial hydrogen production is enhanced in reverse micelles, in order to find green alternatives for the surfactant/solvent mixture conventionally used. Publications: Brentner, L. B.; Peccia, J.; Zimmerman, J. B., Challenges in Developing Biohydrogen as a Sustainable Energy Source. Environmental Science and Technology 2010, 44 (7), 2243-2254. Extraction of Algal Lipids for Use in Biodiesel Production The objective of this research is to contribute to the development of algal lipids as a viable biofuel energy source by optimizing lipid extraction techniques for efficiency, sustainability, decreased hazard, and selectivity. Conference Presentations: “Biodiesel Production Potential of Algal Lipids Extracted with Supercritical Carbon Dioxide,” Lindsay Soh, Jordan Peccia, Julie B. Zimmerman ACS Fall 2010 National Meeting and Exposition, Boston, MA; Green Solvents for Synthesis, Alternative Fluids in Science and Application, Berchtesgaden, Germany; 4th Annual Algae Biomass Summit, Phoenix, AZ. Grants: National Science Foundation: Exploring the Relationships between Gene Regulation and Microbial Ecology for the Sustainable Production of Microalgaebased Biofuels, 2009-2012 Fellowship awarded to Lindsay Soh: US EPA STAR Fellowship

Visible Light Sensitization of TiO2 Semiconductor Surfaces for Use in Solar Cells This research focuses on the visible light sensitization of titanium dioxide (TiO2) semiconductor surfaces with metal complexes and their applications to solar energy conversion in sensitized solar cells and catalysis.


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Research: Systems Algal Biodiesel Lifecycle Analysis Lifecycle analysis (LCA) tools are being used to evaluate design considerations for optimization of biodiesel production from algae. Conference Presentation: “Lifecycle assessment of algal biodiesel: A model to guide process design for industrial production,” Laura B. Brentner, Julie B. Zimmerman 14th Annual Green Chemistry and Engineering Conference, Washington D.C.

Improving the Life-Cycle of Biodiesel in Uganda through Green Chemistry This research focuses on the industrial life-cycle of biodiesel production in East Africa from non-food oilseed crops, with an eye toward producing valuable co-products from the biomass residues.

Lifecycle Assessment of Chitosan This work seeks to quantify the environmental impacts of manufacturing the biopolymer chitosan from chitin. Data is being collected from various chitosan manufacturing plants, covering several different methods of chitosan production.  This project will analyze the environmental impacts at different steps of the processes and provide a basis for comparing chitosan to other chemicals used in the application areas.


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Research: Water Biopolymer Sorbents for Arsenic Removal This research is aimed at developing biopolymer-based sorbents for removal of arsenic from water. This project involves synthesis, characterization, and evaluation of TiO2 -impregnated chitosan bead sorbents. Batch studies have shown that these materials are capable of removing both arsenite and arsenate from water. UV irradation enhances removal capacity for both forms of inorganic arsenic and is able to harness the photocatalytic power or TiO2 to oxidize arsenite to arsenate. This is noteworthy because arsenite is 10 times more toxic than arsenate and is more difficult to remove than arsenate. Publications: Miller, S. M.; Zimmerman, J. B., Novel, bio-based, photoactive arsenic sorbent: TiO2-impregnated chitosan bead. Water Research 2010,44 (19), 5722-5729. Conference Presentations: “Bio-based Arsenic Sorbent” Sarah M. Miller, Julie B. Zimmerman American Chemical Society Spring 2009 National Meeting and Exposition, San Francisco, CA “Toward implementation of a novel, bio-based arsenic sorbent,” Sarah M. Miller 14th Annual Green Chemistry and Green Engineering Conference, Washington, D.C. Grants: National Science Foundation: Mechanistic Laboratory and Field Evaluation of Sustainable Point-of-Use Water Treatment Technologies to Remove Turbidity and Deactivate Coliform Bacteria, 2007-2011 National Science Foundation: Targeted Design of Biomaterials for Water Treatment: Arsenic Removal and Recovery, 2009-2012

Civil Infrastructure Systems: Fostering Leapfrog Adoption of Green Infrastructure through Optimization of Urban Storm Water and Nitrogen Cycles Comprehensively evaluating and modeling green and grey stormwater systems to optimize environmental function, geospatial placement, and social and economic benefit to leapfrog current costly infrastructure design and support local, state, and federal policy-making for sustainable stormwater systems investments. This project brings together students, faculty, citizens, and local, state and federal policy-makers in partnership to meet four aims: 1) critical review of current green infrastructure knowledge and implementation; 2) place-based characterization of hydrologic/nitrogen cycling by and socio-economic function of green infrastructure (south-, centraland northeastern urban seaboard); 3) GIS-supported geospatial optimization of hydrologic/nitrogen cycles by varying location of green infrastructure practices; 4) development of decision-support and policy recommendations for bestpractice in green infrastructure investment.


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Research: Water MUSES Project Center researchers are modeling and analyzing the use, efficiency, value and governance of water as a material in the Great Lakes region through an integrated approach. The main objective of MUSES project is to propose frameworks for assessing the value of water as a material for informed water use decision-making and policies promoting a sustainable future for the Great Lakes region in the face of climate change. Publications: Mo, W.; Nasiri, F.; Eckelman, M. J.; Zhang, Q.; Zimmerman, J. B., Measuring the Embodied Energy in Drinking Water Supply Systems: A Case Study in Great Lakes Region, Environmental Science & Technology, 2010 44 (24), 95169521. Conference Presentations: “Urban Water Reclamation-Reuse Planning and Management: A System Dynamics Approach,” Fuzhan Nasiri, Troy Savage, Ranran Wang, Nico Barawid, and Julie B. Zimmerman CRMGERAD-MITACS Joint Workshop on Decision Analysis and Sustainable Development, Montreal, QC, Canada Grant: National Science Foundation: Collaborative Research: Modeling and Analyzing the Use, Efficiency, Value and Governance of Water as a Material in the Great Lakes Region Through an Integrated Approach, 2007-2012

Wastewater Treatment and Algae This project seeks to identify research priorities for using wastewater as a nutrient source for algae biofuel. This project is preparing a perspective on the history of algal biofuel research and algal wastewater treatment research.  The historical foundation is followed by a review of literature on the process of feeding wastewater to algae both for treatment and for biofuel.  We will provide a discussion based on the reviewed science of prioritized research areas, technological potential, and policy implications for realizing the potential of wastewater-fed microalgal biofuels.


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Research: Education

Yale School of Engineering and Applied Science and The Engineering and Science University Magnet School Partnership The SEAS and ESUMS Partnership pairs Yale graduate level engineering students and teachers in the New Haven Public Schools. The Engineering graduate students are given the opportunity to work in the New Haven community and enhance their own learning experiences. Yale graduate students assist teachers in the classroom, lending an extra hand, providing instruction, and enhancing the learning experience for the young students. These engineering graduate students also serve as role models for continuing science education.

Green Chemistry and Green Engineering Web Curriculum The Center has contributed modules to the Carnegie Mellon Institute for Green Science “Learning Green” website. Learning Green is a free resource aimed at undergraduate students.  It includes video lectures, reading assignments, exercises, and quizzes. The website is: http://igs.chem.cmu.edu

High School Green Chemistry and Green Engineering Course A green Chemistry & Green Engineering course taught by the Center’s graduate students for 10th graders in New Haven, offered through Yale’s SCHOLAR program. Conferences: “Green chemistry and engineering course for Yale/New Haven’s summer SCHOLAR program,” Sarah M. Miller 14th Annual Green Chemistry and Engineering Conference, Washington D.C.


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Research: Education Green Chemistry and Green Engineering Courses Taught at Yale University World Water (ENVE330) This course will explore the complex issues associated with water, global trends, and sustainability.  Topics will range from sources to meet current water needs for human consumption, industry, agriculture, recreation and ecosystem services, and the state of these sources under future scenarios of status quo, global warming, population growth, and the industrialization of developing nations.  The course will also cover the fundamentals of water chemistry, the current design of water and wastewater treatment and distribution systems, an analysis of these designs through Green Engineering, and innovations for future designs including providing services without significant infrastructure.  There will also be elements of the course focused on water policy, environmental justice, and the economic valuation of water globally.  This course will also have a one-credit elective laboratory for the students to conduct experiments related to water treatment processes in the developed and developing world, particularly point of use water treatment systems. Green Engineering and Sustainability (ENVE 360/ENAS 360/ENAS 660) This course will focus on a green engineering design framework, The 12 Principles of Green Engineering, highlighting the key approaches to advancing sustainability through engineering design. This class will begin with discussions on sustainability, metrics, general design processes, and challenges to sustainability. The current approach to design, manufacturing, and disposal will be discussed in the context of examples and case studies from various sectors. This will provide a basis for what and how to consider when designing products, processes, and systems to contribute to furthering sustainability. The fundamental engineering design topics that will be addressed include toxicity and benign alternatives, pollution prevention and source reduction, separations and disassembly, material and energy efficiencies and flows, systems analysis, biomimicry, and life cycle design, management, and analysis. Science to Solutions: How Should We Manage Water (F&ES 610a) While there are many different approaches to understanding and managing environmental problems, most involve three major steps:  (i) describing/understanding the nature of the problem and its causes; (ii) using technical, policy, social and other management tools/processes to help address it; while (iii) recognizing/making the value judgments embedded in each (what problems/data are “important”?  what solutions are “best”?).  The purpose of this introductory course is to illustrate how an MEM student might integrate scientific understanding with management choices as part of an effort to address any particular environmental issue.  Ideally, it should help students choose areas of specialization, as well as improve their ability to engage in integrative problem solving – both in their final semester and after they graduate. The class is focused on water issues, but the integrative structure of the class could be used on other problems as well.  The class is built around a case study approach, in which the faculty bring their different perspectives to bear on understanding and addressing the issues raised in a diverse set of cases, including:  the “dead zone” in the Gulf of Mexico; the New York City drinking water supply; Australia’s response to water scarcity; the Cochabamba “water wars”; and invasive species in the Great Lakes. Greening Business Operations  (F&ES 886a/FES 380) The course examines various industries from engineering, environmental, financial perspectives, and emphasizes increasingly detailed analyses of corporate environmental performance. Methods are drawn from operations management, industrial ecology, and accounting and finance to investigate industrial processes, the potential to pollute, and the environmental and business implications of various sustainability approaches. Life cycle assessment and environmental cost accounting are typical tools that are taught; the class also involves several field trips to companies.


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Research: Policy & Outreach Toxic Substances Control Act (TSCA) Policy Reform The Center is working to identify the role green chemistry can play in modern US chemical policy. This project is carrying out policy analysis on how to lower the barriers to implementing safer chemistry in addition to regulatory pathways. The work is considering international policy space on chemicals management including an analysis of successes and challenges, as well as a similar analysis for state-level green chemistry policies. The focus is not simply on regulation or risk but includes elements to support and enhance innovation and the role that chemical hazard can play in policymaking. Publications: “Integrating Green Chemistry and Green Engineering into the Revitalization of the Toxic Substances Control Act” by Kira Matus, Evan Beach and Julie Zimmerman (This whitepaper can be read at greenchemistry.yale.edu/policy-outreach) Matus, K. J. M; Zimmerman, J. B.; Beach, E. S., A Proactive Approach to Toxic Chemicals: Moving Green Chemistry Beyond Alternatives in the “Safe Chemicals Act of 2010”. Environmental Science & Technology 2010, 44 (16), 60226023. Grant: Kendeda Fund: TSCA Reform: Integrating Green Chemistry and Green Engineering into the Revitalization of the Toxic Substances Control Act, 2010-2012

Writing About Green Science for Mainstream Press Dr. Evan Beach and Dr. Adelina Voutchkova are Environmental Health News Science Communication Fellows for 2010. Every month they contribute to “New Science” and “Media Review” blogs for the website environmentalhealthnews.org. These articles are aimed at explaining recently published developments in green chemistry and engineering and providing feedback to professional journalists who cover related issues.

The Center for Green Chemistry & Green Engineering Online Stay up to date with The Center website featuring the latest news, publications, research projects and member bios. greenchemistry.yale.edu The Center has launched semi-annual newsletters, sending Center news, publications, and higlights directly to your email. Sign up for the newsletters on the Center’s website: greenchemistry.yale.edu/join-our-mailing-list Now you can follow The Center on Twitter! @YaleGCGE


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Research: Policy & Outreach Promoting Green Chemistry and Green Engineering The Center strives to be a source of up-to-date information about successes and challenges in the field of green science.  Center members have published tutorials, perspectives, and review articles, and traveled widely to advocate green principles. Publications: Cui, Z.; Beach, E. S.; Anastas, P. T., Green Chemistry in China. Manuscript in review. Boyle, C.; Mudd, G.; Mihelcic, J. R.; Anastas, P. T.; Collins, T.; Culligan, P.; Edwards, M.; Gabe, J.; Gallagher, P.; Handy, S.; Kao, J.; Krumdieck, S.; Lyles, L. D.; Mason, I.; Mcdowall, R.; Pearce, A.; Riedy, C.; Russell, J.; Schnoor, J. L.; Trotz, M.; Venables, R.; Zimmerman, J. B.; Fuchs, V.; Miller, S.; Page, S.; Reeder-Emery, K., Delivering Sustainable Infrastructure that Supports the Urban Built Environment. Environmental Science & Technology 2010, 44, 4836-4840. Anastas, P. T.; Eghbali, N., Green Chemistry: Principles and Practice. Chemical Society Reviews 2010, 39 (1), 301312. Anastas, P. T., The Essential Bill Glaze. Environmental Science & Technology 2010, 44 (19), 7181-7183. Anastas, P. T., 2020 visions. Nature 2010, 463 (7277), 26-32. Conferences:

Evan Beach “Plastics additives and green chemistry,” 14th Annual Green Chemistry and Engineering Conference, Washington D.C.; Innovation for Sustainable Production (i-SUP 2010), Bruges, Belgium, SETAC North Atlantic Chapter Annual Meeting and Green Chemistry Short Course; University of Connecticut Occupational and Environmental Health Center Symposium, Storrs, CT; Guangdong Senior Executive Program; American Industrial Hygiene Association Connecticut River Valley Conference. Zheng Cui “Green Chemistry in China,” 14th Annual Green Chemistry and Engineering Conference, Washington D.C. Julie Zimmerman “Rational Design of Safer Chemicals,” Gordon Research Conference on Green Chemistry, Davidson, NC; “Meeting Global Water Challenges through Green Chemistry and Engineering”, Gordon Research Conference on Environmental Sciences: Water, Holderness, NH; “Natural Coagulants and Novel Biomaterials for Arsenic Removal from Water“, Department of Geography and Environmental Engineering, Johns Hopkins University, Baltimore, MD.


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Twelve Principles of Green Chemistry 1.Prevention It is better to prevent waste than to treat or clean up waste after it is formed. 2. Atom Economy Synthetic methods should be designed to maximize the incorporation of all materials used in the process into the final product. 3. Less Hazardous Chemical Syntheses Wherever practicable, synthetic methodologies should be designed to use and generate substances that possess little or no toxicity to human health and the environment. 4. Designing Safer Chemicals Chemical products should be designed to preserve efficacy of function while reducing toxicity. 5. 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. 6. 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.

7. Use of Renewable Feedstocks A raw material or feedstock should be renewable rather than depleting whenever technically and economically practicable. 8. Reduce Derivatives Unnecessary derivatization (blocking group, protection/deprotection, temporary modification of physical/chemical processes) should be avoided whenever possible. 9. Catalysis Catalytic reagents (as selective as possible) are superior to stoichiometric reagents. 10. Design for Degradation Chemical products should be designed so that at the end of their function they do not persist in the environment and break down into innocuous degradation products. 11. 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. 12. 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.

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


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Twelve Principles of Green Engineering 1. Inherent Rather Than Circumstantial Designers need to strive to ensure that all materials and energy inputs and outputs are as inherently nonhazardous as possible.

7. Durability Rather Than Immortality Targeted durability, not immortality, should be a design goal.

2. Prevention Instead of Treatment It is better to prevent waste than to treat or clean up waste after it is formed.

8. Meet Need, Minimize Excess Design for unnecessary capacity or capability (e.g., “one size fits all”) solutions should be considered a design flaw.

3. Design for Separation Separation and purification operations should be designed to minimize energy consumption and materials use.

9. Minimize Material Diversity Material diversity in multicomponent products should be minimized to promote disassembly and value retention.

4. Maximize Efficiency Products, processes, and systems should be designed to maximize mass, energy, space, and time efficiency.

10. Integrate Material and Energy Flows Design of products, processes, and systems must include integration and interconnectivity with available energy and materials flows.

5. Output-Pulled Versus Input-Pushed Products, processes, and systems should be “output pulled” rather than “input pushed” through the use of energy and materials.

11. Design for Commercial “Afterlife” Products, processes, and systems should be designed for performance in a commercial “afterlife.”

6. Conserve Complexity Embedded entropy and complexity must be viewed as an investment when making design choices on recycle, reuse, or beneficial disposition.

12. Renewable Rather Than Depleting Material and energy inputs should be renewable rather than depleting.

Anastas, P.T., and Zimmerman, J.B., “Design through the Twelve Principles of Green Engineering”, Env. Sci. Tech. 2003, 37(5), 94A-101A.


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Annual Report 2010

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Yale Green Chemistry 2010 Annual Report