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Green Chemistry Across the Curriculum At St. Olaf College Bob Hanson BCCE20, Indiana University, July 28, 2008 A Project

Green Chemistry Across the Curriculum At St. Olaf College Bob Hanson BCCE20, Indiana University, July 28, 2008 A Project Supported By the W.M. Keck Foundation. Goals of Green Chemistry at St. Olaf. Alter the chemistry curriculum 1 st year, 2 nd year, 3 rd year

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Green Chemistry Across the Curriculum At St. Olaf College Bob Hanson BCCE20, Indiana University, July 28, 2008 A Project

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  1. Green Chemistry Across the CurriculumAt St. Olaf CollegeBob HansonBCCE20, Indiana University, July 28, 2008A Project Supported By the W.M. Keck Foundation

  2. Goals of Green Chemistry at St. Olaf • Alter the chemistry curriculum • 1st year, 2nd year, 3rd year • Design a science facility that reflects this effort • LEED Gold Building www.stolaf.edu/sciencecomplex/

  3. Web App: Green Chemistry Assistant http://fusion.stolaf.edu/gca A collaborative project between St. Olaf College and US EPA - an extension of the EPA Green Chemistry Expert System SMART module

  4. Wittig Reaction Atom Economy – 30.3% E-Factor – 58.5 : 1 GCA Graphical Output Desired Product Coproduct Other materials Solvents Catalysts Ring Closing Metathesis of Diethyl Diallylmalonate Atom Economy – 88.3% E-Factor – 25.5 : 1

  5. GCA graphics

  6. GCA graphics

  7. Cl2 Br2 I2 Heptane EtOAc 1st Year: Periodic Trends & Solubility • Lab Manual includes “Green Connections” and new pre-/post-lab questions • Replace heptane with ethyl acetate • Volatile but with lesser hazards • Option as a renewable resources • Potentially less harmful degradation products • Observed color differences • Chlorine: colorless, Bromine: orange, and Iodine: yellow • Replace chromate anion with thiosulfate anion and eliminate barium cation

  8. Ethanol oxidation: kinetics study Eliminate the chromate oxidation process. Uses household bleach (6% sodium hypochlorite solution) Eliminates concentrated hydrochloric acid Mystery Product Reactions Replace permanganate with iodine redox system Eliminates phosphoric and hydrochloric acids 70% waste reduction (30 L annually) 1st Year Experimental Changes 7 experiments revised & changes implemented

  9. CuCl2·2H2O CuCl2

  10. Efforts: Students typically work in groups of two or three. Each group is required to appoint one student who will take responsible for accounting for group waste and filling out “waste manifests” for their group. Results (unquantified): Students are far more aware of waste issues. Students like taking some responsibility in this regard. Faculty become more aware of waste issues as well. Safety discussions and awareness arise spontaneously. 1st Year Waste Management Introduction

  11. 2nd Year: Sonogashira Coupling Reaction 20+ experiments evaluated and 7 changed Palladium (5%) and copper (8%) catalyzed coupling of terminal alkynes with aryl halides Uses product made in 1st lab of second semester, PEG 200 solvent Microwave 1 minute at 240 Watts Moderate success recycling catalysts and PEG solvent

  12. Ring Closing Metathesis Catalytic ring closure with production of ethylene Microwave for heating … proceeded to 98.3% conversion Polyethylene glycol solvent potential to recycle the catalyst low toxicity, biodegradability, and low vapor pressure modest catalyst recycling success More 2nd Year Experimental Pursuits

  13. Infuse Analytical & Physical labs with green chemistry principles Develop appropriate metrics Test metrics and apply to current lab experiments (benchmarking) Determine labs with the least green characteristics NFPA  3 High material/solvent use High energy use Nonrenewable feedstocks Stoichiometric reactions Reduce waste stream Develop new or modified experiments Change chemistry or chemical system Reducing material/solvent use in currents labs Make volumetric reductions Analysis of citrus fruit essential oils by GC, GC/MS, Raman and/or IR-ATR. 3rd Year: Goals & Objectives

  14. Analytical Lab Benchmarks

  15. 3rd Year: Solvent Reduction - HPLC Discovery HS C18 75 x 3 mm (3.5 mm dp), 20 mL inj, 254 nm detection; 68:30:1.5:0.5 Water:MeOH:formic acid:triethylamine; 0.50 mL/min. Analytes: a) procainamide, b) qunidine, c) lidocaine, d) diisopyramide. 75% solvent reduction, 50% time reduction

  16. Analytical Metrics

  17. 3rd Year: Volumetric Reduction - Downsizing • Iron determination via bipyridine complexation • Automation (robotic) vs. human (volumetric) method. • Challenge – maintain # sig figs and solution handling. AAE 79.87% 79.87% AME 1.67x10-5% 3.34x10-5% MME 4.77x10-6% 9.53x10-6%

  18. 3rd Year: New Citrus Oil Analysis Why is lemon oil used for some consumer products and orange oil for others? How chemically similar are citrus oil extracts? How would you determine this when starting with a piece of fruit (grapefruit, lemon, lime, or orange) and doing as little sample preparation as possible? . SAMPLING STRATEGIES • Solid Phase Microextraction • Peel / zest into vial • PMDS-DVB fiber • Supercritical CO2 extraction • Peel / zest into centrifuge tube • Dry ice & water bath

  19. Physical Properties of CO2 CO2 (l) Good solvent for small, nonpolar molecules: hydrocarbons < 20 carbon atoms & some aldehydes, esters, and ketones

  20. Headspace Samples of Citrus Zest Orange Lime Lemon Grapefruit GC Conditions: VF-5 capillary column (30 m x 0.25 mm x 0.23 mm film), splitless inj 250 °C; column oven hold 50 °C 1 min, 10 °C/min, hold 240 °C for 10 min; helium carrier gas 30 cm/s. MS Conditions: EI, Full scan 40-350 m/z. SPME: PDMS-DVB fiber, 65 mm, 30 s retracted headspace exposure.

  21. Interdisciplinary Investigative Interactive Innovative Interconnected Inviting Integrity Green Team, Builder (Boldt), Architect (Holabird & Root) LEED Gold target Building as Teacher Life-cycle costs Chemical Fume Hood Reductions (energy, operations, first costs) 120,000 NASF, 26 teaching labs Informal gathering spaces designed to extend learning beyond the classroom and laboratory. Green roof terrace Adjacent landscape Water management basins New Science Facility Sept. 1, 2008 Opening 65% decrease for intro/2nd year chemistry (2.5 linear ft/student std) 40% decrease across facility compared to initial design

  22. Future/On-going Work • Continue development and implementation in first two years of curriculum, particularly in the area of waste management and safety • Ramp up development and implementation in third year of curriculum • Piloting upper level p-chem lab (aqueous SEC w/proteins & dextrans to calculate virial coefficients) • LEED-NC Innovation Credit – Green Chemistry & Hood Reduction • Hire another Post-Doc (Enquire here!)

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