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Green Chemistry at Wellesley College:


Green Chemistry: Theory and Practice, by Paul T. Anastas and John C. Warner ... Kurt Stickley. Wellesley College. D. Wicht Green Chemistry at Wellesley College ... – PowerPoint PPT presentation

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Title: Green Chemistry at Wellesley College:

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
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
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
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
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
  • To Introduce the 12 Principles of Green
  • 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
Determine Class Schedule
January 2005
1st Day Exercise to Precede Introduction of 12
  • 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

Started with a reaction they learned in Organic
Chemistry the prerequisite course
Recall the Oxidation of Cyclohexanol from Organic
  • 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
Real Data from Organic Chem Lab
Reminded them of the Analytical Techniques Used
by Chemists
Guided Group Discussion
As a Chemist, what do you need to consider about
this process?
More Guided Group Discussion
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
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
Provided Thought Questions as a Guide to Reading
  • 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
  • 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?

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
  • 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

Presentation Requirements
  • PowerPoint Presentation
  • At least 15 minutes with 5 minutes for
  • Incorporate a Green Chemistry product or
  • 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

Some Presentation Topics
  • Green Dry Cleaning Flourinated Surfactants in
    Supercritial Carbon Dioxide
  • No More Spitting into the Ocean Safer Marine
  • 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

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
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.

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
  • 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.

  • 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!
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
The Students!
Shelley, Jess, Kate, Maggie, Rachel, Erika,
Chikoti, Nooshin, Christina and Mimosa
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