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ANNUAL REPORT 2012

Center for Green Chemistry & Green Engineering at Yale


Center for Green Chemistry & Green Engineering at Yale Yale University

225 Prospect Street New Haven, CT 06520 phone: 203.432.5215 greenchemistry@yale.edu visit us at http://greenchemistry.yale.edu http://twitter.com/YaleGCGE


GREEN CHEMISTRY & GREEN ENGINEERING at YALE

Managing Directors: Paul Anastas, PhD Director Teresa and H. John Heinz III Professor in the Practice of Chemistry for the Environment

Dr. Paul T. Anastas has appointments in the School of Forestry and Environmental Studies, Department of Chemistry, and Department of Chemical Engineering and serves as the Director of the Center for Green Chemistry and Green Engineering at Yale. Before returning to Yale in 2012, Dr. Anastas served as the Assistant Administrator for the US Environmental Protection Agency and the Agency Science Advisor from 2009-2012. From 2004 -2006, Paul Anastas served as Director of the ACS 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.

Julie B. Zimmerman, PhD Associate Director, Research Donna L. Dubinsky Associate Professor of Environmental Engineering Department of Chemical and Environmental Engineering School of Engineering and Environmental Studies

Dr. Julie Beth Zimmerman’s research interests broadly focus on green chemistry and engineering with specific emphasis on green downstream processing and life cycle assessment of algal biomass for fuels and value-added chemicals as well as novel biobased sorbents for purification of drinking water and remediation of industrial wastewater. Other ongoing focus areas include the design of safer chemicals from first principles and the implications of nanomaterials on human health and the environment. Further, to enhance the likelihood of successful implementation of these next generation designs, Dr. Zimmerman studies the effectiveness and impediments of current and potential policies developed to advance sustainability. Together, these efforts represent a systematic and holistic approach to addressing the challenges of sustainability to enhance water and resource quality and quantity, to improve environmental protection, and to provide for a higher quality of life.

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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Administrative Staff:

PhD Students:

Erin McBurney

Aaron Bloomfield

Senior Administrative Assistant

PhD Candidate, Chemistry

Janice Mitchell

Samuel Collom

Administrative Assistant

Research Staff: Katalin Barta, PhD Associate Research Scientist

Barry Husowitz, PhD Associate Research Scientist

Azadeh Kermanshahi Pour, PhD Postdoctoral Fellow

Francisco Lopez Laboratory Assistant

Toby Sommer, PhD Associate Research Scientist

Brian Weeks Research Assistant

PhD Candidate, Chemistry

Thomas Kwan PhD Student, Environmental Engineering

Amanda Lounsbury PhD Student, Environmental Engineering

Lauren Martini PhD Candidate, Chemistry

Leanne Pasquini PhD Candidate, Environmental Engineering

Lindsay Soh PhD Candidate, Environmental Engineering

Jamila Saifee Yamani PhD Candidate, Environmental Engineering

Ranran Wang PhD Student, Environmental Science

Visiting Researchers:

Masters Students:

Camille Brun

Troy Savage

Undergraduate Student, Chemistry; Ecole Nationale de Chemie Physique et Biologie de Paris, France

Chunchi Chen, PhD Postdoctoral Fellow; Academia Sinica Institute of Chemistry, Taiwan

Luis Armando Becerra Pérez Faculty of Economy and International Relations Autonomous University of Baja California Mexico

Thorsten vom Stein

Master’s Candidate, Environmental Science

Undergraduate Students: Yale College ‘12

Yale College ‘13

Megan Altizer Bezawit Getachew Matthew Spaulding Genoa Warner

Yale College ‘14

Yale College ‘15

Emily Hong Lucia Huang Andrew Marburg

Alex Co Holly Hajare

PhD Candidate, Chemistry Technische Chemie ITMC RWTH Aachen Germany

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GREEN CHEMISTRY & GREEN ENGINEERING at YALE

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 include the following: 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 GC&GE are rapidly spreading through both industrialized nations and the emerging Partnerships 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 GC&GE can only provide meaningful impact on the challenges of global sustainability when Collaborations 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

Green Chemistry & Green Engineering Center members have collaborated internationally on the topics within Green Chemistry and Green Engineering such as innovation, plastic addictives, risk assessment, the future of Green Chemistry and implementation in the United States and abroad.

Related Publications: Anastas, Paul T.; Zimmerman, Julie B. eds., Innovations in Green Chemistry and Green Engineering, Selected Entries from the Encylopedia of Sustainability Science and Technology. Springer, 2012. Beach, E. S.; Weeks, B. R.; Stern, R.; Anastas, P. T., Plastics additives and green chemistry. Pure Applied Chemistry_2013,_85 (8), 1611-1624 in press. Cote, I.; Anastas, P. T.; Birnbaum, L. S.; Clark, R. M.; Dix, D. J.; Edwards, S. W.; Preuss, P. W., Advancing the Next Generation of Health Risk Assessment. Environmental Health Perspectives 2012, 120, 1499-1502. Li, C. J.; Anastas, P. T., Green Chemistry: present and future. Chemical Society Reviews 2012, 41 (4), 1413-1414. Matus, K. J. M.; Clark, W. C.; Anastas, P. T.; Zimmerman, J. B., Barriers to the Implementation of Green Chemistry in the United States. Environmental Science & Technology 2012, 46 (20), 10892-10899. Matus, K. J.M.; Xiao, X; Zimmerman, J. B., Green chemistry and green engineering in China: drivers, policies and barriers to innovation. Journal of Cleaner Production 2012, 32, 193-203.

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GREEN CHEMISTRY & GREEN ENGINEERING at YALE

RESEARCH: MATERIALS

Catalytic Transformation of Lignin Model Compounds and Biomass Development of new earth-abundant metal catalysts for selective transformation of lignin model compounds and lignocellulosic biomass. This project aims to selectively defunctionalize lignin while preserving aromaticity and a useful degree of complexity. It is important to develop biomass as a renewable source of chemicals but we must strive to do so in a sustainable fashion. Conversion of lignin from agricultural waste and energy crop residues to higher-value products has potential to produce chemicals and fuels without competing with food resources. The fundamental catalytic chemistry has already been established for the most part using precious metals. The price and scarcity of these metals may exclude them from practical applications in industrial-scale biomass conversion. Our goal is to use cheaper, more abundant metals for these catalytic steps. The chemistry of the expensive metal complexes can be used to help guide the development of cheaper metal alternatives. The development of catalysts based on abundant metals would have important impacts beyond biomass chemistry as well.

Presentations:

Differing Selectivities in Mechanochemical versus Conventional Solution Oxidation of a Lignin Model with Oxone. Sam Collom, Paul Anastas, Evan Beach, Robert Crabtree, Nilay Hazari, Toby Sommer -Bristol-Myers Squibb Symposium, New Haven, CT -1st Engineering Tech Forum, Storrs, CT

Related Publications:

Collom, S. L.; Anastas, P. T.; Beach, E. S.; Crabtree, R. H.; Hazari, N.; Sommer, T. J., Differing Selectivities in Mechanochemical versusConventional Solution Oxidation using Oxone. Tetrahedron Letters 2013, 54 (19), 2344-2347. Hansen, T. S.; Barta, K.; Anastas, P. T.; Ford, P. C.; Riisager, A., One-pot reduction of 5-hydroxymethylfurfural via hydrogen transfer from supercritical methanol. Green Chemistry 2012, 14, 2457-2461. 6


RESEARCH: MATERIALS

Tailored Design of Carbon Nanotubes (CNTs) for Reduction of Unintended Environmental Implications Working with the 12 Principles of Green Engineering in the development of a design framework for tailored Carbon Nanotubes (CNT) cytotoxicity to inform life cycle inventories for impact assessment on promising applications for CNTs. Carbon nanotubes (CNTs) have unique properties that are being exploited for numerous potential applications in nearly every industry. Both single-walled (SWNTs) and multi-walled (MWNTs) carbon nanotubes present possible environmental and human health hazard. While CNT applications have potential to positively influence promotion of alternative energy to therapeutic drug delivery, responsible implementation is essential to the sustainability of the nanotechnology industry. Therefore, it is essential to further understand and identify the specific properties of CNTs that govern cytotoxicity. With this knowledge, future design and manufacture of CNTs can be tailored for specific applications to avoid unnecessary deleterious impacts.

Publications:

Pasquini, L.; Hasmi, S. M.; Sommer, T.; Elimelech, M.; Zimmerman, J. B., Impact of Surface Functionalization on Bacterial Cytotoxicity of Single-Walled Carbon Nanotubes. Environmental Science & Technology 2012, 46 (11), 6297-6305.

Presentations:

A New Perspective on Carbon Nanotube (CNT) Cytotoxicity: MWNTs Exhibit Equivalent Loss of Cell Viability as SWNTs (poster) Leanne Pasquini, Julie B. Zimmerman Sustainable Nanotechnology Organization, Arlington, VA Understanding the Impact of SWNT Aggregation on Toxicity to Inform Greener Nano Design Leanne Pasquini, Julie B. Zimmerman SETAC North America 33rd Annual Meeting, Long Beach, CA

Percent loss of E.coli cell viability upon contact with three different MWNT deposit layers illustrating the range in sample cytotoxic potential compared with a pristine SWNT sample.

Loss of Cell Viability (%)

100 80

SWNT

MWNT_1

60 MWNT_2

40 20

Ball-Milled MWNT_1

0 7


GREEN CHEMISTRY & GREEN ENGINEERING at YALE

RESEARCH: ENERGY RESEARCH: ENERGY

One-pot extraction and transerification of algal lipids This research aims to extract and transesterify algal lipids in one step for the direct production of biodiesel from algae feedstocks. The implementation of algae as a fuel source is hindered by gaps in technology making the biodiesel production process currently inefficient. Life-cycle analysis (LCA) of the biodiesel production process highlights the potential significant impact of a more effective single-step lipid extraction and transesterification process. This research seeks to combine these steps by utilizing heterogeneous catalysts and supercritical carbon dioxide (scCO2) as a green solvent for both the extraction and transesterification of triglycerides to biodiesel. This worked is aimed at providing a low temperature and thus low energy reaction system with the potential to produce biodiesel efficiently, selectively, and sustainably.

FAME CO 2

Schematic of triglyceride transesterification using supercritical carbon dioxide and methanol with heterogeneous catalysts to produce fatty acid methyl esters (biodiesel).

FAME

catalyst scCO 2 + MeOH TG

DG

MG

glycerol

CO 2

Presentations:

One-Pot Algal Biodiesel Production Using Supercritical Carbon Dioxide (Poster) Lindsay Soh, Julie B. Zimmerman Green Chemistry Gordon Research Conference/Seminar, Barga, Italy Algal biodiesel production in supercritical carbon dioxide Lindsay Soh, Julie B. Zimmerman -American Chemical Society National Meeting, San Diego, CA. -International Symposium on Supercritical Fluids, San Francisco, CA. -16th Annual Green Chemistry & Engineering Conference, Washington, DC.

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RESEARCH: MATERIAL

Designing Chemicals for Reduced Toxicity This work on green chemical design aims to understand the pathways that link fundamental chemical properties to harmful effects on human health and the environment. The goal is to publish design guidelines to serve as a first-level toxicity screening tool for new commercial chemicals, or existing chemicals used in new products and formulations. The Center’s approach combines elements of mechanistic analysis, computational chemistry, and statistics to identify ranges and bounds for chemical properties that are most correlated with specific harmful effects in organisms. Case studies on acute and chronic toxicity of chemicals to aquatic species were completed in 2011. Ongoing work is investigating machine learning techniques as a way to improve the analysis.

Related Publications:

Riederer, A. M.; Belova, A.; George, B. J.; Anastas, P. T., Urinary Cadmium in the 1999–2008 U.S. National Health and Nutrition Examination Survey (NHANES). Environmental Science & Technology 2013, 47 (2), 1137-1147. Kostal, J.; Voutchkova-Kostal, A.; Weeks, B.; Zimmerman, J.; Anastas, P., A Free Energy Approach to the Prediction of Olefin and Epoxide Mutagenicity and Carcinogenicity. Chemical Research in Toxicology 2012, 25 (12), 2780-2787. Voutchkova, A.; Beothling, R.; Anastas, P. eds., Designing Safer Chemicals, Volume 9 of Handbook of Green Chemistry Series. Wiley-VCH, 2012

Presentations:

Designing Benign Chemistries Julie B. Zimmerman SETAC North America 33rd Annual Meeting, Long Beach, CA

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GREEN CHEMISTRY & GREEN ENGINEERING at YALE

RESEARCH: SYSTEMS

Biodegradation of Renewable Surfactants Our previous studies have shown that C-glycosides are a promising family of bioderived surfactants with good performance characteristics and a small environmental footprint. Preliminary biodegradation and toxicity studies focused on OECD standard methods. However, given the unique structural features of these chemicals, we are interested in the details of the breakdown mechanism, to better understand the potential environmental fate. Working with a mixed bacterial culture from the New Haven water treatment plant, we have identified one of the major metabolites of the prototype surfactant. Characterization is being accomplished through use of advanced analytical instrumentation including FT-ICR-mass spectrometry and multinuclear NMR spectroscopy.

Enzymatic Hydrolysis of Tetraselmis suecica Cell Wall: Toward a Carbohydrate Biorefinery The carbohydrate components of microalgae are promising raw materials for fermentation processes such as bioethanol production. This project aims to characterize the cell wall composition of a model marine organism, T. suecica, to evaluate its potential as a source of biofuel or value-added projects. We are using analytical techniques to track the monomeric composition of the cell wall as a function of the cell growth cycle and nutrient conditions. We are also using transmission electron microscopy to visualize the cell wall morphology and thickness, to better understand how cultivation conditions affect the processability of the biomass resource.

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RESEARCH: WATER

Sustainable Remediation of Metal Contaminants from Wastewater: A Novel Nano Metal Oxide Impregnated Chitosan-Based Adsorbent The goal of this research is to design an adjustable system that be adapted for wastewater streams of any composition and continuous flow design, currently focusing on remediation of selenium. Given the environmental challenges associated with wastewater remediation and the desire to design a technology to address this challenge with a solution that is itself sustainable, we have developed a chitosan-based nano-metal impregnated adsorbent. This technology exploits the high surface area and affinity of nano-metal oxides for many target contaminants (like arsenic and selenium) while being simple and sustainable during the implementation phase. We have already demonstrated improved remediation of arsenic, and hope to use similar ideas for successful remediation of and reduction of selenium. We are also looking for innovative methods of selective removal of these target contaminants in the presence of background ions that have been known to inhibit removal efficiency.

Related Publications:

Yamani, J. S.; Miller, S. M.; Spaulding, M. L.; Zimmerman, J. B., Enhanced arsenic removal using mixed metal oxide impregnated chitosan beads. Water Research 2012, 46 (14), 4427-4434.

A) Mixed beads

As(III)

As(V)

oxidation

Al

abs

orp

tion

Ti

As(V) UV light As(III)

oxidation

As(V)

A) Mixed batch

As(V)

ion diffus

Ti

abs orp

tion

Ti

Al

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GREEN CHEMISTRY & GREEN ENGINEERING at YALE

RESEARCH: WATER

Life Cycle Assessment of Green and Gray Stormwater Infrastructures To better inform decision makers for greener and sustainable stormwater management, this research assessed and compared life-cycle environmental impacts of green, gray, and integrated green & gray stormwater infrastructures, accounting the influences of variable local characteristics and future dynamics. Major results from this life cycle analysis research have shown that new stormwater infrastructures can significantly improve water quality and aquatic ecosystem health, but at the cost of added resource consumption and elevated GHG emissions and human toxicity impacts during the infrastructures’ construction, operation, and maintenance phases. Given the impacts of climate change, infrastructures with larger treatment capacity and higher resiliency are needed in order to effectively alleviate the impacts associated with more intense, more frequent stormwater events.  Also, improvement in infrastructure design and engineering (e.g. using low-impact or recycled materials or enhancing treatment efficiency) can largely offset the extra environmental impacts caused by the need of infrastructure upsizing. Reducing land imperviousness is an effective substitute to building new stormwater infrastructures. Finally, results have also shown, the assessment and implementation of integrated stormwater infrastructure systems and integrated wastewater and stormwater management can better assist decision makings with tradeoff dilemmas. 

Presentations:

Water and Energy Nexus: Vicious Cycle, Tradeoff, or Coupled Solution? (poster) Ranran Wang, Julie Zimmerman NSF CMMI Engineering Research and Innovation Conference, Boston, MA    Life Cycle Assessment of Green & Gray Stormwater Infrastructures Ranran Wang 29th FES Annual Doctoral Conference, Yale University, New Haven, CT Consequential Life Cycle Analsyis of Green vs. Grey Infrastructure for Stormwater Management Julie B. Zimmerman SETAC North America 33rd Annual Meeting, Long Beach, CA

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Biobased Feedstocks Workshop in Washington, DC The Nicholas Institute for Environmental Policy Solutions at Duke University and the Center for Green Chemistry & Green Engineering at Yale University hosted the Biobased Feedstocks, Supply Chain Risks and Rewards workshop in Washington, DC in November. The workshop was possible with support from Yale Center for Business and the Environment, Deloitte, Biotechnology Industry Organization (BIO), and the American Chemical Society. Duke and Yale Universities gathered representatives from industry, government, and academia to present their perspectives and discuss the economic, policy, and resource impacts of converting to biobased, renewable feedstocks for energy, chemicals, and materials production. The workshop concluded with an open discussion on prioritizing the actions, drivers, challenges, tools, and techniques needed to encourage the adoption

Green Chemistry and Engineering Leadership Program The Center is coordinating an international effort to train young scientists for future leadership roles in the field. In 2011 the Center convened distinguished scientists in the fields of green materials, chemistry, engineering, and energy to plan a program for identifying and supporting next generation leaders. The group will work to establish a system to match postdoctoral researchers and junior faculty members with opportunities in the field. The group also intends to organize a series of workshops to provide networking opportunities, encourage outreach to allied fields, and provide training in outreach to journalists and policymakers.

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Green Chemistry & Green Engineering In The Field GREEN CHEMISTRY & GREEN ENGINEERING at YALE

P2 Science: A Case Study Based on Yale Research

Dr. Patrick Foley, a graduate of Yale University’s Environmental Engineering program in 2011, patented with Paul Anastas and The Center for Green Chemistry and Yale a C-glycosides surfactant technology that lead to the development of P2 Science.

The Development of P2 Science

P2 Science has developed a unique biorefining process that produces specialty chemicals for fragrance & flavor ingredients derived from vegetable oils instead of the currently used petrochemicals. These vegetable derived chemicals can serve as replacements for petrochemical aldehydes used in fragrances. These have proven to be attractive to many major industrial user and fragrance formulators. The company’s long-term goals are to market novel chemicals.

The Technology

P2’s technology is a new take on an established process to provide improved efficiency, safety and value. The P2 process is a hybrid ozonolysis process cleaving double-bonds in vegetable oils, resulting in di-acids and linear aldehydes. The linear aldehydes can be used in flavors and fragrances, or as precursors to high-value cosmetic ingredients.

The Team:

Rob Bettigole, Chairman Neil A. Burns, CEO Patrick Foley, PhD, Chief Scientific Officer Diana Hu, Market Analyst

Learn More about P2 www.p2science.com

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Green Chemists & Engineers in the Community Science Lessons for a New Haven School:

This spring 5 Center graduate students and staff volunteered to give a science lesson at Roberto Clemente Leadership Academy, a New Haven Public School. Center members designed an activity on biomimicry to help celebrate Earth Day with the students and spent a little time talking about pursuing science in education and careers.

A Nano Literature Club:

During the summer of 2012, PhD Candidate Leanne Pasquini met weekly with two local high school students to form a “nano literature club.� The group took turns finding and presenting an article of interest found in either popular media or from primary literature related to nanotechnology such as nanotechnology for the advancement of cancer therapeutics and the current (non)regulation of nanomaterials.

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GREEN CHEMISTRY & GREEN ENGINEERING at YALE

Yale Green Chemists & Engineers in the Field The Center’s alumni are advancing their careers in Green Chemistry and Green Engineering across the globe. Former graduate students and postdocs are now professors at prestigous schools, consultants, and leaders in industry.

Yale  Green  Chemists  and  Engineers   In  The  Field   Academia  

Industry  

Consul9ng  

4%   7%   26%   63%  

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government  


Yale Green Chemists & Engineers in the Field Dr. Sarah Miller

AAAS Fellow Directorate for Computer & Information Science & Engineering Division of Computer and Network Systems

Since graduating from Yale University in 2012, Sarah is currently a AAAS Science Policy Fellow at the National Science Foundation in the Computer, Information Science, and Engineering Directorate.  She now works on federal programs that seek to improve computer science and engineering education.

Dr. Adelina Voutchkova-Kostal Assistant Professor Department of Chemistry

Adelina Voutchkova-Kostal’s research group at GW aims to address the urgent need to develop more environmentally benign methodologies for the fine chemicals industry, specifically exploring novel multifunctional catalysts that improve atom/ energy economy, allow the use of renewable feedstocks and minimize the toxic waste streams released into the environment. Dr. Voutchkova-Kostal’s group also focuses on rational design of safer industrial chemicals, aims to address the urgent need to develop methods for minimizing the probability that a new chemical will have adverse biological effect before it is ever synthesized.Voutchkova-Kostal Lab. Website: http://home.gwu.edu/~avoutchkova

Dr. Matthew Eckelman

Assistant Professor Department of Civil and Environmental Engineering Northeastern University

Dr. Eckelman graduated from Yale University in the department of Environmental Engineering in 2009 and worked with the Zimmerman lab as a postdoctoral associate. He has an expertise in Environmental impacts of metals production, use, emissions, and recovery, life cycle assessment, systems modeling of bioenergy and bio-based industrial chemicals, and material and energy use in urban environments and civil infrastructure. Website: http://www.civ.neu.edu/people/eckelman.html

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GREEN CHEMISTRY & GREEN ENGINEERING at YALE

Green Chemistry & Green Engineering Partners at Yale The Center partners with several different groups across the University to explore new research opportunities and innovation collaborations. The Center has been fortunate to work with and learn from colleagues in the Department of Chemistry, School of Engineering and Applied Sciences, as well as the School of Forestry and Environmental Studies including these outstanding research groups. Professor Menachem Elimelich’s group research centers on problems involving physicochemical and biophysical processes. Their work concentrates on engineered and natural environmental systems focused on environmental applications and implications of nanomaterials, membrane separations for desalination and water reuse, engineered osmosis for sustainable production of water and power, as well as water and sanitation in developing countries. Website: http://www.yale.edu/env/elimelech/Research_Page/Research_page.html Professor Nilay Hazari’s research group is developing organometallic catalysts that activate carbon dioxide and facilitate its conversion to organic carboxylates. They are optimizing the structure of palladium cross-coupling catalysts to increase their activity and stability, significantly decreasing the amount of catalyst required. Website: http://www.yale.edu/hazarigroup/ Professor William Jorgensen’s group examines organic, medicinal, and computational chemistry to simulate reactions and computer-aided drug discoveries. The tools produced by the Jorgensen group are used in collaboration with the Center for design guidelines for chemicals with reduced toxicity. Website: http://www.JorgensenResearch.com Professor Jordan Peccia’s research group foscuses on microalgae biofuels as an answer to many of the sustainability and economic limitations recently ascribed to petroleum and plant-based biofuels; the Peccia group is a leader in the study of pathogens emitted during biosolids land application, and bioaerosols, investigating the integration of physical aerosol processes with molecular biology-based tools to describe the dynamics and sources of biological aerosols in the indoor environment. Website: http://www.eng.yale.edu/peccialab/index.html

Green Energy Consortium The Yale Energy initiative aims to demonstrate the feasibility of using oxomanganese catalysts immobilized on TiO2 nanoparticles (NPs) to achieve photocatalytic water oxidation. The consortium is lead by Yale Professors and co-PIs, Victor Batista, Gary Brudvig, Robert Crabtree, and Charles Schmuttenmaer. Funded by the U.S Department of Energy, the group has developed an interdisciplinary team with expertise in catalyric surface complexes, computational modeling, femtosecond spectroscopy, and quantitative electrochemical studies of oxidation chemistry in relation to fuel production.

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Professor Robert Crabtree’s group research focuses on finding organometallic complexes that act as catalysts. The group looks at improving atom economy of reactions and storing and releasing hydrogen as an alternative to fossil fuels. Website: http://ursula.chem.yale.edu/~crabtree Professor Gary Brudvig’s group is studying the mechanisms for photosynthesis examining how plants can do water oxidation, and what can be learned to put towards synthetic catalysts for doing the same reaction. The group also examines solar energy and dye sensitized solar cells. Website: http://ursula.chem.yale.edu/~brudvig Professor Charles Schmuttenmaer’s group focuses on laser spectroscopy to direct time-resolved studies, utilizing visible, UV, and IR lasers with the ability to use a subpicosecond timescale for far-infarerd (FIR) region of the spectrum to better determine matter that was before unable to be seen. Website: http://thz.yale.edu/ Professor Victor Batista’s group complements this experimental work with theoretical calculations to examine modeling and explaining physical bases behind the strength of a catalyst. Website: http://www.chem.yale.edu/~batista/ Learn more about the Green Energy Consortium: http://www.chem.yale.edu/~green/

Center for Business and the Environment at Yale The Yale Center for Business and the Environment (CBEY) is involved in programs and initiatives focused on outreach, education and research. Through the involvement of students, faculty, and strategic partners, CBEY is actively involved in areas from environmental finance to corporate environmental strategy. Interdisciplinary projects include: • Conservation Finance Camp Carbon Finance Speaker Series • Sabin Environmental Venture Prize and Speaker Series • Environmental Economics Research Seminar • Sustainability Leaders Series • Business and the Environment Consulting Clinic • Case Study Development • Yale Community Carbon Fund • Renewable Energy and International Law Network

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GREEN CHEMISTRY & GREEN ENGINEERING at YALE

Undergraduate Students in The Center Undergraduate students fromYale College and abroad play an important role in the Center for Green Chemistry & Green Engineering. They offer assistance in the lab while gaining technical skills. Project Manager, Dr. Evan Beach explains, “The one-on-one mentorship gives

undergrads the experience of working on a research project that requires a greater level of independence. They get to see how a lab operates on a day to day basis and the process of presenting results and getting feedback from colleagues.” The Center currently has four undergraduates in the labs, all with unique experiences and aspirations for their future goals. Alex Co is currently assisting a project on the biodegradation of a surfactant. He explains he has

“seen parallels with what I am researching in the lab and what I’m learning class.”

Alex has discovered an interest in policy as well as chemistry and working with the researchers in the Center has encouraged him to seriously consider graduate school. Alex has been asked to write about his experiences for ACS GCI’s newsletter, The Nexus, to be published online in February.

Holly Hajare discovered The Center’s website before she was even accepted at Yale and toured the labs during her campus visit. Holly explains that while working with The Center, she has had more opportunities to work with the NMR spectrometers that she hadn’t had in class and has “especially enjoyed working in the group dynamic to analyze data

collaboratively.”

Holly is also a member of the Ballet Company at Yale and plays violin in a Yale orchestra.

Lucia Huang was initially interested in the Center’s interdisciplinary research dynamic. Lucia has had opportunities to work with algae biofuel projects in Professor Zimmerman’s engineering lab as well as the synthesis of lignin projects in Professor Anastas’ chemistry lab. Lucia has aspirations to incorporate her research skills in a future career in business. “Knowing

the Center has spin-off companies and works with other enterprises opens my eyes for possibilities to work in business in the future,” says Lucia.

Lucia is also the President of The Women’s Leadership Initiative at Yale, and a member of the Yale Finance Club for Women.

Andrew Marburg was drawn to Green Chemistry and its mission of sustainable and rational chemical design. He explains working with Dr. Beach has given him valuable research skills including NMR methods for identifying chemical structures. Andrew explains, “The Center

has a collaborative atmosphere and holds regular group meetings, so I’ve been able to learn a bit about the other projects, too.”

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Yale Courses

Offered through Spring 2013 - Fall 2014 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 Sustainable Design (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” and  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. 21


GREEN CHEMISTRY & GREEN ENGINEERING at YALE

RESEARCH: Education

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.

Kroon Hall, Yale University ŠRobert Benson 22


In The Media: Environmental Engineer Visits Group V Inventors Greenwich Academy, January 12, 2012 Green Chemist: A Q&A with Departing EPA Science Advisor Paul Anastas Scientific American, January 17, 2012 The Subaru Plant and the Principles of Green Engineering in Practice Article Myriad, January 17, 2012 ‘Father of green chemistry’ plans return to Yale Yale News, January 26, 2012 The Father of Green Chemistry Forbes, February 2, 2012 Transitioning, Paul Anastas leaves EPA and returns to Yale Chemical & Engineering News, March 5, 2012 ‘Young people get it,’ Yale professor says of fostering Central High students’ interest in science Gazette.net, March 20, 2012

Engineers Develop Sustainable Technique to Remove Arsenic from Water Supplies Yale School of Engineering & Applied Sciences News, June, 2012 Paul Anastas and the Robin Hood Question Green Chemistry, Editorial, July, 2012 ‘Green’ chemist to speak at MSU Times Record News, November, 2012 Ullyot Public Affairs Lecture, 2012 Lecturer: Paul Anastas Chemical Heritage Foundation,  2012 Texas A&M University at Qatar hosts green chemistry and engineering conference Texas A&M University, January, 2013 Julie Beth Zimmerman named to the inaugural Donna L. Dubinsky endowed post Yale News, April 8, 2013

Calls for green building standards YNN, March 29, 2012

Paul Anastas Ph.D. ‘89 delivers annual lecture The Justice - Brandeis University, April 9, 2013

Green Chemistry Guru Comes Home New Haven Independent, April 19, 2012

Green World Chemical Heritage, Spring 2013

Julie Zimmerman to Receive Huber Prize Yale Daily News, May 9, 2012

Green Chemistry, Interview with Paul Anastas Where We Live, WNPR, May 8, 2013

High Hopes for Growing a Green Fuel in Arid East Africa Environment Yale, May 2012 Toward a more economical process for making biodiesel fuel from algae Phys.org, June 19, 2012

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GREEN CHEMISTRY & GREEN ENGINEERING at YALE in the Media

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Center for Green Chemistry & Green Engineering November, 2012 24


Center for Green Chemistry & Green Engineering at Yale 225 Prospect Street New Haven, CT 06520 phone: 203.432.5215 greenchemistry@yale.edu visit us at http://greenchemistry.yale.edu


Yale Center for Green Chemistry & Engineering Annual Report 2012