Green Chemistry & The ACS Green Chemistry Institute

1. Green Chemistry & The ACS Green Chemistry Institute Jennifer L. Young and Jesse Gallun American Chemical Society Capital Science 2008 Conference March 30, 2008 www.acs.org/greenchemistry email: gci@acs.org

2. Outline • History of Green Chemistry • ACS Green Chemistry Institute • U.S. Government, Universities & Other Organizations • Green Chemistry in the Real World • Future Outlook • Research • Education • Awards & Conferences • Industry • International

3. Green Chemistry History in U.S. • Early 1990s started in the U.S. Environmental Protection Agency • green chemistry theories, definitions, publications, conference sessions at ACS National Meetings • ACS convened stakeholders to start award and conference • 1996 first Presidential Green Chemistry Challenge Awards • 1997 first Annual Green Chemistry & Engineering Conference • 1997 Green Chemistry Institute founded

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

5. 12 Principles ofGreen Chemistry • Prevent waste • Maximize atom economy • Design less hazardous chemical syntheses • Design safer chemicals and products • Use safer solvents and reaction conditions • Increase energy efficiency • Use renewable feedstocks • Avoid chemical derivatives • Use catalysts, not stoichiometric reagents • Design chemicals and products that degrade after use • Analyze in real time to prevent pollution • Minimize the potential for accidents Reference: Anastas, P. T. and Warner, J. C. Green Chemistry: Theory and Practice, Oxford University Press: New York, 1998.

6. ACS Green Chemistry Institute • ACS GCI is 10 years old • 1997 – Green Chemistry Institute (GCI) founded as an independent, non-profit organization • 2001 – GCI joined the American Chemical Society (ACS) • Staff • Bob Peoples, Ph. DDirector, ACS Green Chemistry Institute • Jesse Gallun Communications & Outreach Associate • Joyce Kilgore Senior Administrative Associate • Julie ManleySenior Industrial Coordinator • Stacey Trey Conference Coordinator • Jennifer Young, Ph.D.Senior Program Manager

7. ACS Green Chemistry Institute • Mission: to advance the implementation of green chemistry and green engineering principles into all aspects of the chemical enterprise. www.acs.org/greenchemistry

8. Research & Education:Electronic Tools • k • Search for and contribute resources at www.GreenChemEx.org • k • Search for green analytical methods at www.nemi.gov • New research tools are under development by the ACS GCI Pharmaceutical Roundtable with Chemical Abstract Service (CAS)

9. Education: Books

10. Education: Summer School

11. Annual Student Awards • Kenneth G. Hancock Memorial Awards • $1000 research awards sponsored by ACS Environmental Chemistry Division and NIST • Joseph Breen Memorial Fellowship • Travel support to international green chemistry conference

12. Recognizing Innovation: Awards • US Presidential Green Chemistry Challenge • Collaboration of ACS and US EPA • Recognizes improvements from industry, small business, and academia • ACS Award for Affordable Green Chemistry • Endowed by Rohm and Haas Company • Recognizes global scientific discoveries that deliver cost-effective and environmentally friendly products and/or processes

13. Convening Scientists Keynote Speakers • Dr. Theo Colborn – President, The Endocrine Disruption Exchange • Dr. Skip Volante – Vice President, Process Research, Merck & Co, Inc. • Dr. Steven Chu – Director, Lawrence Berkeley National Laboratory • Dr. Bill Banholzer – Chief Technology Officer, The Dow Chemical Company • Jonathan Lash – President, World Resources Institute www.GCandE.org

14. Industrial Implementation: the Business Case • Case studies being used in MBA programs across the U.S. • S.C. Johnson - a study of S.C. Johnson’s Green List. • Tandus - environmental design of flooring products. • TerraCycle - start-up company with new sustainable fertilizer products. • NatureWorks - corn-based “PLA” plastic. • Pfizer - Green Chemistry process redesign yields bottom line results. • Shaw - “Cradle-to-Cradle” design of carpet products. • Archer Daniels Midland - the emerging market for “Greener” paints. • DuPont Cleaning Products Division Canada - strategic green product decisions. Email gci@acs.org for pricing information.

15. ACS GCI Pharmaceutical Roundtable Membershipas of February 1, 2008 Membership is open to all pharmaceutical research, development, and manufacturing companies. The Roundtable will be strongest when all global pharmaceutical corporations are members. Email gcipr@acs.org

16. International Cooperation • 25 Green Chemistry Institute international chapters, at various stages of development • Argentina • Australia • Brazil • Canada • China (People's Republic of China) • Estonia • Ethiopia • Finland • Greece • Hungary • India • Ireland • ACS GCI Pharmaceutical Roundtable created an EU subgroup in 2007 • Italy • Japan • Mexico • Nepal • New Zealand • Senegal • South Africa • Spain • Sweden • Taiwan • Thailand • United Kingdom • Uruguay

17. Outline • History of Green Chemistry • ACS Green Chemistry Institute • U.S. Government, Universities & Other Organizations • Green Chemistry in the Real World • Future Outlook • Research • Education • Awards & Conferences • Industry • International

18. Other Activities in the U.S. • Green Chemistry Research & Development Act • Numerous state-level initiatives • Government Agencies very active in green chemistry & engineering • Universities – developing curriculum, creating research centers, expanding GC networks • Independent Organizations - expanding the influence of GC principles across the chemical enterprise

19. Real Examples of Green Chemistry

20. soy protein soy protein Soy Adhesive • Soy adhesive developed to mimic the adhesion of mussels • Mimics the adhesive protein secreted by mussels (rich in 3,4-dihydroxylphenyl-alanine, lysine, cysteine) • Uses soybean flour, chemically modified with catechol, amino, and mercapto functionality, then cross-linked mercapto-enriched soy protein dopamine-grafted soy protein Li, Oregon State University

21. Soy Adhesive • Soy adhesives used for wood composite • Formaldehyde-free plywood, particleboard, medium density fiberboard • Replaces urea-formaldehyde and phenol-formaldehyde resins for wood composites • Emission of HAPs reduced up to 90% at wood composite production plant • In 2006, over 47 million pounds of urea-formaldehyde resin was replaced with soy adhesive at Columbia Forest Products • Cost competitive • Superior strength properties and water resistance of wood composite Li, Oregon State University, Columbia Forest Products, and Hercules, Inc.

22. Water-based Adhesive • 3M Post-it® Super Sticky Notes use new water-based technology • Solvent-based super-sticky adhesive formulation was developed 10 years ago but wasn’t taken to market because of 3M’s initiative to reduce VOCs • Water-based primer, adhesive and release coating formulations, based on acrylate polymers • Adhesive is based on a proprietary new microsphere technology

23. Water-based Adhesive • Introduced in 2003, for vertical and hard-to-stick surfaces • Had to overcome new challenges in switching from solvent-based to water-based system: • Additives needed in the formulation for balance of stability and stickiness • Changes needed in equipment and process for coating and drying • Cost savings: increased productivity (35% increase in line speed), reduced environmental controls, reduced materials costs

24. Pharmaceuticals Made in Greener Ways • Ibuprofen (anti-inflammatory drug) • Greener route makes the drug in 3 steps instead of 6 • Lipitor® (cholesterol lowering drug) • Greener route uses biotechnology for key chemical steps • Zoloft® (antidepressant drug) • Greener route makes the drug with less waste

25. Ibuprofen – Optimizing Atom Economy • Ibuprofen – new greener route • 3 catalytic steps (vs. 6 stoichiometric in traditional synthesis) • 99% atom utilization (with recovered acetic acid; vs. 40% previously) • Uses HF as catalyst and solvent; replaces AlCl3 • HF is recovered and recycled with > 99.9% efficiency Developed by Hoechst-Celanese (BHC Company)

26. Lipitor® – Using Biocatalysis • Codexis developed key chiral intermediate for Atorvastatin (active ingredient in Lipitor® cholesterol lowering drug) • Synthesis enabled by the directed evolution of 3 biocatalysts • Greatly reduces generation of cyanide waste • 4,000 fold improvement in cyanation reaction volumetric productivity NaCN biocatalyst mild conditions glucose biocatalysts mild conditions Key intermediate, called HN (HydroxyNitrile) multiple steps atorvastatin calcium (active ingredient in Lipitor®)

27. Zoloft® - Reducing Waste • Sertraline is the active ingredient in the antidepressant drug Zoloft® • Pfizer’s new “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

28. Re-formulating for Safer Products • Scientists are re-formulating products to eliminate hazardous chemicals • SC Johnson developed Greenlist™ and used it to reformulate Windex® - resulting in improved performance and a safer product • Nike is also reformulating products to remove toxic chemicals

29. Formulation Ingredients • SC Johnson & Sons’ Greenlist™ is a system that rates the environmental and health effects of ingredients • Scores range Best (3) - Restricted Use Material (0) • Ratings for more than 90% of SCJ’s raw materials, including solvents, surfactants, chelants, propellants, resins, packaging, etc. • Windex® - reformulated using Greenlist™ and improved performance • Other companies are developing ingredient lists: Nike; U.S. EPA and GreenBlue (CleanGredients); others

30. New Materials Derived from Corn • Scientists are making new materials that are derived from corn • NatureWorks LLC makes poly(lactic acid) (PLA) plastic containers and fibers • DuPont makes Sorona® for apparel, upholstery, resins, and nonwoven applications

31. Poly(lactic acid) from NatureWorks LLC • Manufacturing poly(lactic acid) (PLA) from renewable resources • corn or wheat • agricultural waste in future • Uses 20-50% fewer fossil fuels than conventional plastics • The synthesis of PLA produces a high yield, does not require organic solvents, and creates no hazardous materials • PLA products can be recycled or composted • PLA resin can be made into fibers and plastics for consumer goods such as clothing and food packaging • Can produce about 188,000 yogurt cups/acre of corn • Wal-mart is packaging all fresh cut produce in this PLA catalyst, solventless catalyst, solventless fermentation corn

32. Sorona® Fiber from DuPont • Monomer for Sorona®, 1,3-propanediol, is generated from corn using a genetically engineered microorganism • Properties of fabrics include softness, stretch and recovery, easy care, stain resistance, and colorfastness • For use in apparel, upholstery, resins, and nonwoven applications 1,3-propanediol terephthalate Sorona®

33. Group Discussion • As a research chemist, in academia or industry or government, only part of your job is discovering innovative green chemistry technology. • Another important part of your job is convincing your colleagues, funding agency, manager, company, and consumer to accept your green chemistry technology. This is still a huge barrier to implementing green chemistry across the chemical enterprise.

34. Group Discussion Scenario: Greener Plastic Bottles NEW PLASTIC: You discovered a new, greener way to make poly(ethylene terephthalate) PET plastic bottles (soda & water bottles). PROCESS: The polymer product (chemical structure) is the same, but the process is greener than the existing process. Your new process uses one monomer that is derived from a renewable resource, a highly active catalyst at a low level, and generates less waste. The final polymer structure is the same as the one made by the old process, so it still can be made into bottles and recycled in the same way as before. COST: The new process will cost more initially, but as volumes of sales increase, the price will become lower than the polymer made by the old process. Questions: • How do you convince a company to commercialize this new, greener polymer? • How do you convince the consumers to buy this new product? • In any research setting, how do you convince your peer researchers that this greener polymer is important and scientifically sound (“hard science”)? • In an academic setting, how would you convince a funding agency to fund this research?

35. Thank you! Jennifer Young and Jesse Gallun email: gci@acs.org website: www.acs.org/greenchemistry