LIVE INTERACTIVE LEARNING @ YOUR DESKTOP November 9, 2010 ACS: Incorporating Green Chemistry into...

LIVE INTERACTIVE LEARNING @ YOUR DESKTOP

November 9, 2010

ACS: Incorporating Green Chemistry into the High School Curriculum

Presented by: Michael Tinnesandand

Barbara Sitzman

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?

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.

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 .

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

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

Principles of Green Chemistry

7. Use of Renewable Feedstocks8. Reduce Derivatives9. Catalysis.10. Design for Degradation11. Real-time Analysis for Pollution Prevention12. Inherently Safer Chemistry for Accident Prevention

Paul T. Anastas and John C. Warner, 1998

Let’s pause for questions from the audience

Opinion Poll 1

• List one limitation to including Green Chemistry in a high school chemistry class.

[Type your ideas in the chat]

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.

Opinion Poll 2

• List one positive aspect of infusing Green Chemistry in a high school chemistry class.

[Type your ideas in the chat]

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.

“…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 DivisionJ. Chem. Educ., 2010, 87 (2), p 121

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

Sample labs, demos and activities to Introduce Green Chemistry Principles

1. A convenient liquid CO2 extraction of natural products

2. Vitamin C clock reaction

3. Modeling atom economy

4. Energy required to heat water

A Convenient Liquid CO2 Extraction of a Natural Product

The Royal Society of Chemistry publication, Green Chemistry.L.C. McKenzie, J.E. Thompson, R.Sullivan and J.E. Hutchison, Green Chem., 2004, 6, 355 - 358

A Convenient Liquid CO2 Extraction of a Natural Product

Green Lab - A Convenient liquid CO2 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 CO2 to demonstrate extraction of a nonpolar natural product using a green solvent.

Opinion Poll 3Do your students currently perform a solubility experiment?

Yes No

Is this lab an attractive substitute or addition?

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 EducationWright, Stephen W. The Vitamin C Clock Reaction, J.Chem. Ed., January 2002, 79 (1), p 41-43

Procedure for Clock Reaction

Iodine Clock Reaction Video

I2(aq) + C6H8O6(aq)-> 2H+(aq) + 2I-(aq) + C6H6O6(aq)

2H+(aq) + 2I-(aq) + H2O2(aq) ->I2(aq) + 2H2O(l)

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

What if?

Calculate the possible cumulative effect of not using safer materials.

A traditional clock reaction requires 150mL, 0.01 M HgCl2, 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?

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!

2.0 106 students 0.150 L

2 students

0.01 mol Hg

271.6 gHg

1 mol Hg400,000g Hg

Opinion Poll 4Do you currently do a lab on rates of reaction in your course?

Yes No

Modeling Atom Economy

Calculate the Atom Economy for each reaction

Students use models to build 2-propene two different ways.

How to Calculate Atom Economy

Percent Atom Economy formula weight of desired products

formula weight of all products100%

Reaction 1

Percent Atom Economy 42 gdesired products

119 g total products100% 35% atom economy

Reaction 2

Percent Atom Economy 42gdesired products

60g total products100% 70% atom economy

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

Opinion Poll 5Do you currently ask students to calculate percent yield as part of labs in your course?

Yes No

Energy Required to Heat WaterCompare the efficiency in three methods of heating

Introduction to Green Chemistry, Ryan, M., Tinnesand, M., Eds. (pp. 45-53).

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

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.

Heat Produced by Bunsen burner

Bunsen BurnerCombustion 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

CH4 + 2 O2 CO2 + 2H2O

The combustion reaction involves methane and oxygen combining to form carbon dioxide and water

CH4 + 2 O2 CO2 + 2H2O

Calculate the heat of reaction from standard heat of formation values.

H produced by the reaction (H f products) (H f reactants)

H produced by rxn (CO2 2(H2O)) (CH4 2(02))

Here are the standard heat of formation values:

CO2 = -393.5kJ H20 = -241.8kJCH4 =-74.8kJ O2 = 0 kJ

CH4 + 2 O2 CO2 + 2H2O

H produced by rxn [ 393.5kJ

241.8kJ

mol)] [

74.8 kJ

802.3 kJ

H produced by rxn [CO2 2(H2O)] [CH4 2(02)]

Here are the standard heat of formation values:

CO2 = -393.5kJ H20 = -241.8kJCH4 =-74.8kJ O2 = 0 kJ

CH4 + 2 O2 CO2 + 2H2O

CH4 + 2 O2 2H2O + CO2 Calculated ΔHproduced = -802.3 kJ/mol CH4

Hproduced

heat of reaction

mol CH4

rate L

stime (s)

1 mol CH4

22.4 L

CH4 + 2 O2 2H2O + CO2 Calculated ΔHproduced = -802.3 kJ/mol CH4

Hproduced

heat of reaction

mol CH4

rate L

stime (s)

1 mol CH4

22.4 L

Hproduced

802.3 kJ

1mol CH4

19.9 10 3 L

s245 s

1 mol CH4

22.4 L175 kJ

Energy Absorbed by the Water

Bunsen Burner

The combustion heats 200.0 g H2O from 16.0C to 66.5C, ΔT=50.5C

Habsorbed mass temp specific heat capacity

Energy Absorbed by the WaterBunsen Burner

The combustion heats 200.0 g H2O from 16.0C to 66.5C, ΔT=50.5C

Habsorbed mass temp specific heat capacity

Habsorbed 200.0 g 50.5 C 0.00418 kJ

g C42.2 kJ

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

H produced wattage of hotplate or microwave .001 kJ

Heat Produced by Hot Plate

Hot Plate

698 watt hot plate takes 378 seconds to heat 200.0 g H2O from 16.0C to 66.0C, ΔT=50.0C

H produced 698watt .001 kJ

378 s 264 kJ

Habsorbed 200.0 g 50.0 C .00418 kJ

g C41.8 kJ

Heat Produced by MicrowaveMicrowave

1000 watt microwave takes 60 seconds to heat 200.0 g H2O from 18.0C to 67.0C, ΔT=49.0C

Habsorbed 200.0 g 49.0 C .00418 kJ

g C4 1.0 kJ

H produced 1000watt .001 kJ

60 s 60.0 kJ

Calculated EfficienciesCalculate efficiencies

Efficiency = ΔHabsorbed / ΔHproduced

Bunsen burner efficiency 42.2 kJ

175 kJ100 24.1%

hotplate efficiency 41.8 kJ

264 kJ100 15.8 %

microwave efficiency 41.0 kJ

60.0 kJ100 68.3%

Opinion Poll 6Do you currently do a lab that involves calorimetry in your course?

Yes No

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/educationhttp://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

• 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/

Greener Education Materials for Chemists (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

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/

BibliographyACS 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-cb10-4170-8115-86056b84a762

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/

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

http://learningcenter.nsta.org

http://www.elluminate.com

National Science Teachers AssociationDr. 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 SeminarsPaul Tingler, Director

Jeff Layman, Technical Coordinator

LIVE INTERACTIVE LEARNING @ YOUR DESKTOP November 9, 2010 ACS: Incorporating Green Chemistry into...

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