1. LIVE INTERACTIVE LEARNING @ YOUR DESKTOP November 9, 2010 ACS: Incorporating Green Chemistry into the High School Curriculum Presented by: Michael Tinnesand and Barbara Sitzman

2. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 A.Pollution Prevention Act of 1990 B.The Presidential Green Chemistry Challenge of 1995 C.Oprah’s Favorite Things broadcast of 2002 D.The debut of Al Gore's An Inconvenient Truth in 2006 Quiz from the ACS Green Chemistry Institute http://www.chempower.org/quizintro.html Which of the following events gave birth to today’s Green Chemistry Initiatives?

3. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 What is Green Chemistry? Green Chemistry is the design of chemical products and processes that reduce or eliminate the use and/or generation of hazardous substances.

4. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Green Chemistry is Benign by Design When chemists plan, manufacture, process, use, and dispose of chemical products, they are making determinations about the impact on human health and environment.

5. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Which of the following is NOT among the top 10 benefits of Green Chemistry? A.Energy efficiency B.Fuller, bouncier hair C.Less waste D.Improved environmental and human health

6. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Which of the following is NOT among the top 10 benefits of Green Chemistry? A.Energy efficiency B.Fuller, bouncier hair C.Less waste D.Improved environmental and human health

7. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Principles of Green Chemistry 1. Prevention 2. Atom Economy 3. Less Hazardous Chemical Syntheses 4. Designing Safer Chemicals 5. Safer Solvents and Auxiliaries 6. Design for Energy Efficiency  Paul T. Anastas and John C. Warner, 1998

8. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Principles of Green Chemistry 7. Use of Renewable Feedstocks 8. Reduce Derivatives 9. Catalysis. 10. Design for Degradation 11. Real-time Analysis for Pollution Prevention 12. Inherently Safer Chemistry for Accident Prevention  Paul T. Anastas and John C. Warner, 1998

9. Let’s pause for questions from the audience

10. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Opinion Poll 1 List one limitation to including Green Chemistry in a high school chemistry class. [Type your ideas in the chat]

11. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Barriers to Incorporating Green Chemistry in High School Courses The typical introductory chemistry course is already ‘full’. Lack control of your own curriculum. Beginning students can’t appreciate green innovations. Students confuse environmental with green chemistry. Green Chemistry can carry political baggage. Green Chemistry principles not applicable at high school level. New Greener labs could be expensive.

12. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Opinion Poll 2 List one positive aspect of infusing Green Chemistry in a high school chemistry class. [Type your ideas in the chat]

13. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Benefits of Including Green Chemistry in High School Chemistry Courses Improves academic labs that are not models of best practice. Cumulative effect of sustainable practices is great. Students learn by example, important to set clear priorities early. Activities redesigned to replace current activities, but with a ‘greener’ focus. Activities and labs use commonly available supplies. U.S. Students lag in understanding of topics relevant to everyday life.

14. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 “…while a majority of students are aware of environmental issues, their understanding of the underlying causes of these issues lags behind their awareness…” Mary Kirchhoff, Director, ACS Education Division J. Chem. Educ., 2010, 87 (2), p 121

15. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Green Chemistry can Reinforce Basic Chemistry Concepts Rates of reaction Catalysis Chemical cycles Energy Thermochemistry Experimental design Law of Conservation of Matter Stoichiometry Percent yield Solubility Polarity Phase change Organic chemistry Synthesis

16. Let’s pause for questions from the audience

17. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Sample labs, demos and activities to Introduce Green Chemistry Principles 1.A convenient liquid CO 2 extraction of natural products 2.Vitamin C clock reaction 3.Modeling atom economy 4.Energy required to heat water

18. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 A Convenient Liquid CO 2 Extraction of a Natural Product The Royal Society of Chemistry publication, Green Chemistry.Green Chemistry L.C. McKenzie, J.E. Thompson, R.Sullivan and J.E. Hutchison, Green Chem., 2004, 6, 355 - 358

19. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 A Convenient Liquid CO 2 Extraction of a Natural Product

20. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Green Lab - A Convenient liquid CO 2 extraction of a natural product Chemistry Concepts: Solubility, polarity, phase change Traditional lab: Solubility of polar and non-polar substances demonstrated by dissolving various combinations of nonpolar solutes and solvents Green Chemistry Principle: Using safer solvents The Green fix: Uses the preparation of liquid CO 2 to demonstrate extraction of a nonpolar natural product using a green solvent.

21. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Opinion Poll 3 Do your students currently perform a solubility experiment? Yes No Is this lab an attractive substitute or addition?

22. Let’s pause for questions from the audience

23. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 A Clock Reaction with Safer Substances Solution B: Hydrogen Peroxide Starch Solution Water Solution A: Tincture of Iodine Vitamin C from tablets Water Source: The Journal of Chemical EducationThe Journal of Chemical Education Wright, Stephen W. The Vitamin C Clock Reaction, J.Chem. Ed., January 2002, 79 (1), p 41-43

24. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Procedure for Clock Reaction

25. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Iodine Clock Reaction Video

26. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 A Clock Reaction with Safer Substances I 2 (aq) + C 6 H 8 O 6 (aq)-> 2H + (aq) + 2I - (aq) + C 6 H 6 O 6 (aq) 2H + (aq) + 2I - (aq) + H 2 O 2 (aq) ->I 2 (aq) + 2H 2 O(l)

27. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 A Clock Reaction with Safer Substances Chemistry Concept: Rates of reaction Traditional labs: A number of clock reaction labs using a varying degree of hazardous materials Green Chemistry Principle: Using safer starting materials The Green fix: Iodine Clock reaction using safer household materials

28. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 What if? Calculate the possible cumulative effect of not using safer materials. A traditional clock reaction requires 150mL, 0.01 M HgCl 2, per group of two students. If approximately 2 million introductory students in the U.S. did the safer experiment, how much mercury waste would be avoided?

29. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Mercury calculation Although it may be unlikely for every student in the U.S. to do the same experiment, the cumulative effect of using unsafe substances can still be significant!

30. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Opinion Poll 4 Do you currently do a lab on rates of reaction in your course? Yes No Is this lab an attractive substitute or addition?

31. Let’s pause for questions from the audience

32. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Modeling Atom Economy Calculate the Atom Economy for each reaction Students use models to build 2-propene two different ways.

33. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 How to Calculate Atom Economy

34. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 How to Calculate Atom Economy Reaction 1

35. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 How to Calculate Atom Economy Reaction 2

36. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Modeling Atom Economy Chemistry Concept(s): Law of Conservation of Matter, stoichiometry, percent yield Traditional lab: Percent yield labs, stoichiometry Green Chemistry Principle: The atom economy The Green fix: Uses molecular models to introduce the concept of atom economy as an alternative/replacement to percent yield

37. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Opinion Poll 5 Do you currently ask students to calculate percent yield as part of labs in your course? Yes No Is this lab an attractive substitute or addition?

38. Let’s pause for questions from the audience

39. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Energy Required to Heat Water Compare the efficiency in three methods of heating Introduction to Green Chemistry, Ryan, M., Tinnesand, M., Eds. (pp. 45-53).

40. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Energy Required to Heat Water Chemistry Concepts: Energy, thermochemistry, experimental design, calorimetry Traditional lab: Calculating specific heat capacity of substances. Measuring the heat of combustion using calorimetry Green Chemistry Principle: Using lower amounts of energy in chemical processes The Green fix: Comparing relative amounts of energy for heating substances in the lab

41. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Energy Required to Heat Water For each method of heating water we must do two calculations: 1.The amount of heat produced by the source (Bunsen burner, hot plate, or microwave). 2.The amount of heat absorbed by the water. The amount of heat absorbed, compared to the amount of heat produced by the source, is the efficiency of the heating method.

42. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Heat Produced by Bunsen burner Bunsen Burner Combustion of methane takes 245 seconds (rate of flow = 19.9 x 10 -3 L/s) to heat the water. First, calculate the amount of heat released by the reaction CH 4 + 2 O 2  CO 2 + 2H 2 O

43. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Heat Produced by Bunsen burner The combustion reaction involves methane and oxygen combining to form carbon dioxide and water CH 4 + 2 O 2  CO 2 + 2H 2 O Calculate the heat of reaction from standard heat of formation values.

44. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Heat Produced by Bunsen burner Here are the standard heat of formation values: CO 2 = -393.5kJH 2 0 = -241.8kJ CH 4 =-74.8kJ O 2 = 0 kJ CH 4 + 2 O 2  CO 2 + 2H 2 O

45. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Heat Produced by Bunsen burner Here are the standard heat of formation values: CO 2 = -393.5kJH 2 0 = -241.8kJ CH 4 =-74.8kJ O 2 = 0 kJ CH 4 + 2 O 2  CO 2 + 2H 2 O

46. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Heat Produced by Bunsen burner Bunsen Burner Combustion of methane takes 245 seconds (rate of flow = 19.9 x 10 -3 L/s) to heat the water. CH 4 + 2 O 2  2H 2 O + CO 2 Calculated ΔH produced = -802.3 kJ/mol CH 4

47. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Heat Produced by Bunsen burner Bunsen Burner Combustion of methane takes 245 seconds (rate of flow = 19.9 x 10 -3 L/s) to heat the water. CH 4 + 2 O 2  2H 2 O + CO 2 Calculated ΔH produced = -802.3 kJ/mol CH 4

48. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Energy Absorbed by the Water Bunsen Burner The combustion heats 200.0 g H 2 O from 16.0  C to 66.5  C, ΔT=50.5  C

49. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Energy Absorbed by the Water Bunsen Burner The combustion heats 200.0 g H 2 O from 16.0  C to 66.5  C, ΔT=50.5  C

50. Let’s pause for questions from the audience

51. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Heat Produced by Hot Plate and Microwave The calculations for the heating by the hot plate and microwave oven are similar, the heat produced by the electric sources is easier to calculate if we know the wattage of the device. 1 watt =.001 kJ/second

52. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Heat Produced by Hot Plate Hot Plate 698 watt hot plate takes 378 seconds to heat 200.0 g H 2 O from 16.0  C to 66.0  C, ΔT=50.0  C

53. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Heat Produced by Microwave Microwave 1000 watt microwave takes 60 seconds to heat 200.0 g H 2 O from 18.0  C to 67.0  C, ΔT=49.0  C

54. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Calculated Efficiencies Calculate efficiencies Efficiency = ΔH absorbed / ΔH produced

55. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Opinion Poll 6 Do you currently do a lab that involves calorimetry in your course? YesNo Is this lab an attractive substitute or addition?

56. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 ACS Green Chemistry Teaching Resources Introduction to Green Chemistry: Instructional Activities for Introductory Chemistry Real-World Cases in Green Chemistry, vol I and II Going Green: Integrating Green Chemistry into the Curriculum Greener Approaches to Undergraduate Experiments ACS.org/education http://portal.acs.org/portal/acs/corg/content?_nfpb=true&_pageLabel=PP_SUPERARTICLE&node_id=1444&use_sec=false&se c_url_var=region1&__uuid=1c4c080f-cb10-4170-8115-86056b84a762

57. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Journal of Chemical Education Published by ACS for the ACS Division of Chemical Education. Topics in Green Chemistry (edited by Mary Kirchhoff, ACS Director of Education) provides a forum for dissemination of the latest curricular developments in green chemistry. http://jchemed.chem.wisc.edu/

58. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 Greener Education Materials for Chemists (GEMs)GEMs GEMs is an interactive tool developed by the University of Oregon. Organizes and disseminates core Green Chemistry educational materials. Searchable by level, keyword, topic, more… http://greenchem.uoregon.edu/gems.html

59. ACS-NSTA Green Chemistry Web Seminar, November 9 2010 The Chemical Education Digital Library (ChemEd DL) ChemEd DL aims to provide exemplary digital resources, tools, and online services to aid in teaching and learning chemistry. http://www.chemeddl.org/

60. Bibliography ACS Education Resources http://www.acs.org/education ACS Green Chemistry Resources http://portal.acs.org/portal/acs/corg/content?_nfpb=true &_pageLabel=PP_SUPERARTICLE&node_id=1444&use_sec=false &sec_url_var=region1&__uuid=1c4c080f-cb10-4170-8115- 86056b84a762http://portal.acs.org/portal/acs/corg/content?_nfpb=true &_pageLabel=PP_SUPERARTICLE&node_id=1444&use_sec=false &sec_url_var=region1&__uuid=1c4c080f-cb10-4170-8115- 86056b84a762 Journal of Chemical Education http://jchemed.chem.wisc.edu/ Greener Education Materials for Chemists (GEMS) http://greenchem.uoregon.edu/gems.html Chemical Education Digital Library http://www.chemeddl.org/

61. Thank you to the sponsor of tonight's Web Seminar:

62. http://learningcenter.nsta.org

63. http://www.elluminate.com

64. National Science Teachers Association Dr. Francis Q. Eberle, Executive Director Zipporah Miller, Associate Executive Director Conferences and Programs Al Byers, Assistant Executive Director e-Learning LIVE INTERACTIVE LEARNING @ YOUR DESKTOP NSTA Web Seminars Paul Tingler, Director Jeff Layman, Technical Coordinator