Green Chemistry at Wellesley College:

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Green Chemistry at Wellesley College The
Development of a New Course for January 2005
Wintersession Denyce K. Wicht Assistant
Professor Suffolk University Department of
Chemistry and Biochemistry 41 Temple St. Boston,
MA 02114
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Motivation to Teach this Course
The Green Chemistry in Education
Workshop University of Oregon Eugene, Oregon
July 25- 30, 2004 The Green Chemistry in
Education Workshop is for educators in the
chemical sciences and is designed to cover new
trends in incorporating green or sustainable
chemistry concepts into the chemistry curriculum
and laboratory. The five-day workshop is a
combination of lectures, discussion, and hands-on
time in the laboratory.
Committee on Educational Research and Development
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Where is Wellesley and What is Wintersession?
The mission of Wellesley College is to provide a
strong liberal arts education to women. Its
located 13 miles west of Boston in Wellesley, MA.

Wintersession at Wellesley is a three week period
in January when students may choose to be at the
College to pursue a course or project, try an
internship, work, participate in team sports
training, or simply enjoy the beauty of the
Wellesley campus and a New England winter,
without the pressures of schedules and deadlines.
Wintersession courses are varied, and there are
offerings for credit as well as non-credit.
New credit courses must be approved by the
Committee on Curriculum and Instruction
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Proposed Course Description
Description Green chemistry can be defined as
the design of chemicals, chemical syntheses, and
chemical processes that are environmentally
benign and economically feasible. This course
will serve to introduce students to the 12
Principles of Green Chemistry and explore how
these principles are put into use through real
world examples. This course is designed for
students interested in chemistry, biochemistry,
engineering, environmental studies, materials
science and related fields. Textbooks Green
Chemistry Theory and Practice, by Paul T.
Anastas and John C. Warner Green Chemistry An
Introductory Text, by Mike Lancaster. Credits
0.5 units (Regular non-lab courses are assigned
one unit of credit) There is no laboratory
component to this course Schedule MWTh
900-1100 a.m. Jan 5th-26th Prerequisite
Chem 211 (Organic Chemistry I) Enrollment
Maximum 16 (minimum 6)
Approved by the Committee on Curriculum and
Instruction Fall 2004 Cross-registered in
Chemistry and Environmental Studies
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Define Goals of this Course

• To define, discuss the need for, give a
  historical perspective of, and provide examples
  of Green Chemistry.

This will be an iterative process in which we
will move between big picture topics and very
specific examples involving detailed aspects of
chemistry.

• To Introduce the 12 Principles of Green
  Chemistry.

• To discuss some of the Principles in more
  detailspecifically, atom economy alternative
  feedstocks, catalysis, and solvents.

• To present the critical evaluation of a Green
  Chemistry product or process to the group through
  a 15 minute oral presentation.

Breakdown of Grades Class Participation 50 Or
al Presentation 25 Research
Paper 25 100
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Determine Class Schedule
January 2005
Monday Tuesday Wednesday Thursday Friday
3 4 5 Class One 12 Principles of Green Chemistry 6 Class Two Atom Economy Office Hrs 2-4 7 Presentation/Paper Topic Due
10 Class Three Evaluating Feedstocks 11 Office Hrs. 2-4 12 Class Four Guest Speaker Amy Cannon UMass-Boston 13 Class Five Catalysis Office Hours 2-4 14 List of Primary Citations for Presentation/Paper Due
17 No Classes MLK Day 18 Office Hrs. 2-4 19 Class Six Organic Solvents 20 Class Seven Visit to Pfizer Global Manufacturing in Groton, CT 21
24 Class Eight Presentations Rachel, Mimosa, Maggie, Chikoti, Erika 25 Office Hrs. 2-4 26 Class Nine Presentations Kate, Shelley, Nooshin, Jessica, Christina 27 28 Papers Due
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1st Day Exercise to Precede Introduction of 12
Principles

• The company for which you work provides
  cyclohexanone to a major pharmaceutical company
• The traditional process your company has been
  using is becoming obsolete, as the cost of
  chromium waste treatment and disposal is
  marginalizing the companys profits
• Your supervisor has asked you to propose an
  alternative process for the synthesis of
  cyclohexanone

Started with a reaction they learned in Organic
Chemistry the prerequisite course
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Recall the Oxidation of Cyclohexanol from Organic
Chem

• After a quick search of the literature, you
  find a prep for the oxidation of cyclohexanol to
  cyclohexanone using sodium hypochlorite
  (household bleach) in aqueous acetic acid.
• The pilot plant does a preliminary run of the
  process and the plant engineer provides you with
  the GC-MS data of the product mixture.

Reminded them of the lab in which they did this
reaction
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Real Data from Organic Chem Lab
Reminded them of the Analytical Techniques Used
by Chemists
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Guided Group Discussion
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gt1
As a Chemist, what do you need to consider about
this process?
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More Guided Group Discussion
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27
gt1
As a Green Chemist what do you need to consider
about this process?
From here, the 12 Principles were introduced . . .
Pointed out that our goal is to eliminate the
distinction between a chemist and a green
chemist
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General Model for Subsequent Lectures
Topics related to Atom Economy, Evaluation of
Feedstocks, Catalysis and Solvents were drawn
from the text books. In-class discussions were
supplemented with primary literature articles and
group work.
Example An Efficient and green protocol for the
preparation of cycloalkanols a practical
synthesis of venlafaxine. Tetrahedron Letters
2004, 45, 7291-7295
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Provided Thought Questions as a Guide to Reading
Literature

• The paper states the yields under these
  conditions are low and are not ideally suited to
  large scale industrial synthesis. Why are the
  earlier patented methods not ideally suited to
  large scale industrial synthesis?
• 2. What are the differences in the temperature
  at which the reaction is run in the earlier
  patented methods as compared to the reported
  protocol? How might these differences impact
  energy usage?
• What is the structure of the phase transfer
  catalyst TBAHSO4? How does it work? What does
  needing a phase transfer catalyst imply about the
  solubility of the starting materials? Is this
  surprising?
• 4. The paper states the process is simple to
  operate and eliminates cumbersome purification
  techniques such as column chromatography, making
  it very attractive from a commercial point of
  view. Aside from being cumbersome, what other
  disadvantage might there be to column
  chromatography as a purification technique?

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Other Aspects of the Course

• Group work
• Example
• Calculate the atom economy of the greener
  synthesis of Ibuprofen
• From Cann, M.C. and Connelly, M. E. Real World
  Cases in Green Chemistry, American Chemical
  Society Washington, DC, 2000.
• Library staff briefly introduced/review
  Scifinder
• Amy Cannon discussed her thesis work on
  photovoltaic cells.
• We went out to lunch as a class in order to
  facilitate informal discussions on the general
  topic of green chemistry.
• Trip to Pfizer was excellent!
• Toured the manufacturing facility and the Pfizer
  staff explained the progress they had made in
  process analytical techniques (PAT)
• Culmination of the course the individual
  presentations

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Presentation Requirements

• PowerPoint Presentation
• At least 15 minutes with 5 minutes for
  questions
• Incorporate a Green Chemistry product or
  process
• Comparative and Evaluative
• Accurately citedno websites
• Iterative process between big picture and
  specific examples involving detailed aspects of
  chemistry (or physics or biology)
• Remember, your audience is your peers
• Goal of talk is pedagogical

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Some Presentation Topics

• Green Dry Cleaning Flourinated Surfactants in
  Supercritial Carbon Dioxide
• No More Spitting into the Ocean Safer Marine
  Antifoulants
• Motivating Automotives Combustion Engine
  Technology and the Alternatives.
• Softening Laundry Water and Protecting Natural
  Waters Amino-phosphonates or Zeolite A?
• Blue Bin or Black Box? Do you know what
  happens to your recycled paper? A Report on the
  use of Enzymes in Paper Recycling

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Blue bin or Black box?
Do you know what happens to your recycled
paper? A report on the use of enzymes in paper
recycling Rachel Nelson
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Student Comments Valuable Features

• This course initiated my background in green
  chemistry, a field I was not aware of before. I
  was introduced to quite a few reactions which
  were understandable, but still on a high level,
  both in class and through outside research. This
  definitely forced me to utilize my knowledge of
  organic chemistry in several instances with
  actual applications. The research report was the
  first time I had seriously worked with patents
  and scientific journals, as well as my topic
  (which I randomly chose, only to find out that I
  had no knowledge of it whatsoever). I have come
  away from this course with fairly in depth
  knowledge of a previously unknown topic, as well
  as an overview of green chemistry.
• I really appreciated the field trip and the
  independent project. That allowed for application
  of the knowledge. The small class atmosphere
  also allowed for discussion.
• Learning more about exactly what green
  chemistry is the field trip to Pfizer showed the
  theory in action in the real world.
• This course really brought chemistry to a real
  world level for me. I got to see how the
  chemistry I already knew for the most part could
  be made more environmentally friendly and even
  cheaper through green chemical principles.

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Student Comments Features to Improve

• A larger focus on how actual products and
  applications of green chemical process have
  changed the environment would have solidified the
  course. A laboratory experience to
  compare/contrast the green chemical route would
  also have helped bring the course out from theory
  into reality.
• It would have been nice to do some sort of lab
  activities.
• This is a really interesting course that I
  think should be taught during a regular semester.
  Green chemistry encompasses a lot of different
  issues that we didn't get a chance to cover.
• The only improvement would be for this
  course to be longer - i.e. a semester course. I
  was very disappointed when it was over.

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Conclusions

• Experimental or non-traditional academic
  periods are especially amenable
• to the development of a green chemistry course.
• Length and content of course can be tailored to
  meet various teaching needs if
• the 12 Principles are used as a general outline
  for the course.
• Incorporate aspects of previous courses into
  green chemistry course, particularly
• the prerequisite.
• Individual presentations and field trip were
  viewed as valuable features of
• the course.
• Suggestions for improvement semester long
  course and the incorporation of
• a lab.

OverallFeedback was positive!
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Acknowledgments
Green Chemistry In Education Workshop 2004 at the
University of Oregon Jim Hutchinson Ken
Doxsee Julie Haack Lallie Cobb McKenzie Kristi
Mikkelsen David Brown Davidson College Rich
Gurney Simmons College
Amy Cannon University of Massachusetts-Boston Pf
izer Global Manufacturing Buzz Cue Rich
Williams Laurie St. Pierre Berry Frank
Sistare Carlos Mojica Kurt Stickley
Wellesley College
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The Students!
Shelley, Jess, Kate, Maggie, Rachel, Erika,
Chikoti, Nooshin, Christina and Mimosa