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ACS: Incorporating Green Chemistry
into the High School Curriculum
Presented by: Michael Tinnesand
and
Barbara Sitzman
November 9, 2010
Which of the following events gave birth
to today’s Green Chemistry Initiatives?
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
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.
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 .
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
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
ACS-NSTA Green Chemistry Web Seminar, November 9 2010
Principles of Green Chemistry
1.
2.
3.
4.
5.
6.
Prevention
Atom Economy
Less Hazardous Chemical Syntheses
Designing Safer Chemicals
Safer Solvents and Auxiliaries
Design for Energy Efficiency
 Paul T. Anastas and John C. Warner, 1998
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
ACS-NSTA Green Chemistry Web Seminar, November 9 2010
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]
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.
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]
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.
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
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
ACS-NSTA Green Chemistry Web Seminar, November 9 2010
Let’s pause for questions
from the audience
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
ACS-NSTA Green Chemistry Web Seminar, November 9 2010
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
ACS-NSTA Green Chemistry Web Seminar, November 9 2010
A Convenient Liquid CO2 Extraction of a
Natural Product
ACS-NSTA Green Chemistry Web Seminar, November 9 2010
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.
ACS-NSTA Green Chemistry Web Seminar, November 9 2010
Opinion Poll 3
Do your students currently
perform a solubility experiment?
Yes
Is this lab an attractive substitute
or addition?
ACS-NSTA Green Chemistry Web Seminar, November 9 2010
No
Let’s pause for questions
from the audience
A Clock Reaction with
Safer Substances
•Solution A:
•Tincture of Iodine
•Vitamin C from tablets
•Water
•Solution B:
•Hydrogen Peroxide
•Starch Solution
•Water
Source: The Journal of Chemical Education
Wright, Stephen W. The Vitamin C Clock Reaction, J.Chem. Ed., January 2002, 79 (1), p 41-43
ACS-NSTA Green Chemistry Web Seminar, November 9 2010
Procedure for Clock Reaction
ACS-NSTA Green Chemistry Web Seminar, November 9 2010
Iodine Clock Reaction Video
ACS-NSTA Green Chemistry Web Seminar, November 9 2010
A Clock Reaction with
Safer Substances
I2(aq) + C6H8O6(aq)-> 2H+(aq) + 2I-(aq) + C6H6O6(aq)
2H+(aq) + 2I-(aq) + H2O2(aq) ->I2(aq) + 2H2O(l)
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
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
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?
ACS-NSTA Green Chemistry Web Seminar, November 9 2010
Mercury calculation
2.0  10 6 students 
0.150 L
0.01 mol Hg 271.6 g Hg


 400,000g Hg
2 students
1L
1 mol Hg
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!
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
Is this lab an attractive substitute
or addition?
ACS-NSTA Green Chemistry Web Seminar, November 9 2010
No
Let’s pause for questions
from the audience
Modeling Atom Economy
Students use models to build 2-propene two different ways.
Calculate the Atom Economy for each reaction
ACS-NSTA Green Chemistry Web Seminar, November 9 2010
How to Calculate
Atom Economy
Percent Atom Economy 
formula weight of desired products
 100%
formula weight of all products
ACS-NSTA Green Chemistry Web Seminar, November 9 2010
How to Calculate
Atom Economy
Reaction 1
formula weight of desired products
Percent Atom Economy 
 100%
formula weight of all products
42g desired products
Percent Atom Econom y
 100%  35% atomeconom y
119g total products
ACS-NSTA Green Chemistry Web Seminar, November 9 2010
How to Calculate
Atom Economy
Reaction 2
formula weight of desired products
Percent Atom Economy 
 100%
formula weight of all products
42g desired products
Percent Atom Econom y
 100%  70% atomeconom y
60g total products
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
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
Is this lab an attractive substitute
or addition?
ACS-NSTA Green Chemistry Web Seminar, November 9 2010
No
Let’s pause for questions
from the audience
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).
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
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.
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
CH4 + 2 O2 CO2 + 2H2O
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
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)
ACS-NSTA Green Chemistry Web Seminar, November 9 2010
Heat Produced by Bunsen burner
Here are the standard heat of formation values:
CO2 = -393.5kJ
CH4 =-74.8kJ
H20 = -241.8kJ
O2 = 0 kJ
CH4 + 2 O2 CO2 + 2H2O
H produced by the reaction  (H f products)  (H f reactants)
H produced by rxn  (CO2  2(H2O))  (CH4  2(02 ))
ACS-NSTA Green Chemistry Web Seminar, November 9 2010
Heat Produced by Bunsen burner
Here are the standard heat of formation values:
CO2 = -393.5kJ
CH4 =-74.8kJ
H20 = -241.8kJ
O2 = 0 kJ
CH4 + 2 O2 CO2 + 2H2O
H produced by the reaction  (H f products)  (H f reactants)
H produced by rxn  [CO2  2(H2O)]  [CH4  2(02 )]
H produced by rxn  [
393.5kJ
241.8kJ
74.8 kJ
0 kJ
802.3 kJ
 2(
)]  [
 2(
)] 
mol
mol
mol
mol
mol
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.
CH4 + 2 O2 2H2O + CO2
Calculated ΔHproduced = -802.3 kJ/mol CH4
1 m olCH
heat of reaction rate L
4 
H


 tim e(s) 
produced
m olCH
s
22.4 L
4
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.
CH4 + 2 O2 2H2O + CO2
Calculated ΔHproduced = -802.3 kJ/mol CH4
1 m olCH
heat of reaction rate L
4 
H


 tim e(s) 
produced
m olCH
s
22.4 L
4
1 m olCH
802.3 kJ 19.9  103 L
4  175 kJ
H


 245 s 
produced 1m olCH
s
22.4 L
4
ACS-NSTA Green Chemistry Web Seminar, November 9 2010
Energy Absorbed by the Water
Bunsen Burner
The combustion heats 200.0 g H2O from 16.0C to 66.5C,
ΔT=50.5C
H absorbed  mass   temp  specific heat capacity
ACS-NSTA Green Chemistry Web Seminar, November 9 2010
Energy Absorbed by the Water
Bunsen Burner
The combustion heats 200.0 g H2O from 16.0C to 66.5C,
ΔT=50.5C
H absorbed  mass   temp  specific heat capacity
H absorbed
0.00418 kJ
 200.0 g  50.5 C 
 42.2 kJ

g C

ACS-NSTA Green Chemistry Web Seminar, November 9 2010
Let’s pause for questions
from the audience
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
.001kJ s
H produced  wattageof hotplateor m icrowave
  tim e
watt
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 H2O from
16.0C to 66.0C, ΔT=50.0C
H absorbed
.00418 kJ
 200.0 g  50.0 C 
 41.8 kJ

g C
H produced  698watt 

.001kJ
watt
s  378s  264 kJ
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 H2O from
18.0C to 67.0C, ΔT=49.0C
H absorbed
.00418 kJ
 200.0 g  49.0 C 
 4 1.0 kJ

g C
H produced 1000watt 

.001kJ s
watt
 60 s  60.0 kJ
ACS-NSTA Green Chemistry Web Seminar, November 9 2010
Calculated Efficiencies
Calculate efficiencies
Efficiency = ΔHabsorbed / ΔHproduced
42.2 kJ
Bunsen burner efficiency 
 100  24.1%
175 kJ
41.8 kJ
hotplate efficiency 
 100  15.8 %
264 kJ
41.0 kJ
microwave efficiency 
 100  68.3 %
60.0 kJ

ACS-NSTA Green Chemistry Web Seminar, November 9 2010
Opinion Poll 6
Do you currently do a lab that
involves calorimetry in your
course?
Yes
Is this lab an attractive substitute
or addition?
ACS-NSTA Green Chemistry Web Seminar, November 9 2010
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/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
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/
ACS-NSTA Green Chemistry Web Seminar, November 9 2010
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
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/
ACS-NSTA Green Chemistry Web Seminar, November 9 2010
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-cb10-4170-811586056b84a762
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 Association
Dr. Francis Q. Eberle, Executive Director
Zipporah Miller, Associate Executive Director
Conferences and Programs
Al Byers, Assistant Executive Director e-Learning
NSTA Web Seminars
Paul Tingler, Director
Jeff Layman, Technical Coordinator
LIVE INTERACTIVE LEARNING @ YOUR DESKTOP