D. Wicht Green Chemistry at Wellesley College August 2 nd, 2006 Green Chemistry at Wellesley...

D. Wicht Green Chemistry at Wellesley College August 2nd, 2006

Green Chemistry at Wellesley College: The Development of a New Course for

January 2005 Wintersession

Denyce K. WichtAssistant ProfessorSuffolk University

Department of Chemistry andBiochemistry 41 Temple St.

Boston, MA 02114


Motivation to Teach this Course

The Green Chemistry in Education WorkshopUniversity 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


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.

Where is Wellesley and What is Wintersession?

New credit courses must be approved by the Committee on Curriculum and Instruction

The mission of Wellesley College is to provide a strong liberal arts education to women. It’s located 13 miles west of Boston in Wellesley, MA.

Wintersession courses are varied, and there are offerings for credit as well as non-credit.


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. WarnerGreen 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 9:00-11:00 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 chemistry.

• To Introduce the 12 Principles of Green Chemistry.

• To discuss some of the Principles in more detail—specifically, 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%Oral Presentation: 25% Research Paper: 25%

100%


Monday Tuesday Wednesday Thursday Friday

3 4 5 Class One12 Principles of Green Chemistry

6 Class TwoAtom Economy

Office Hrs 2-4

7Presentation/Paper Topic Due

10 Class ThreeEvaluating Feedstocks

11 Office Hrs. 2-4

12 Class FourGuest Speaker:Amy Cannon UMass-Boston

13 Class FiveCatalysis

Office Hours 2-4

14List of Primary Citations for Presentation/Paper Due

17

No ClassesMLK Day

18

Office Hrs. 2-4

19 Class SixOrganic Solvents

20 Class SevenVisit to Pfizer Global Manufacturing in Groton, CT

21

24 Class EightPresentations:Rachel, Mimosa, Maggie, Chikoti, Erika

25

Office Hrs. 2-4

26 Class NinePresentations:Kate, Shelley, Nooshin, Jessica, Christina

27 28Papers Due

Determine Class Schedule

January 2005


1st Day Exercise to Precede Introduction of 12 Principles

OH O

+ H2CrO4

H2SO4

H2O+ H2CrO3 + H2O

• 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 company’s 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


OH O

NaOCl+ + NaCl + H2O

CH3CO2H

H2O

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


0

O

OH

O

O

O

Cl

58%

14% > 1%27%

Reminded them of the Analytical Techniques Used by Chemists

Real Data from Organic Chem Lab


OH O

Cl

O

O

O

NaOCl + NaCl + H2O

CH3CO2H

H2O+ + +

58% 27% >1%

Guided Group Discussion

As a Chemist, what do you need to consider about this process?


OH O

Cl

O

O

O

NaOCl + NaCl + H2O

CH3CO2H

H2O+ + +

58% 27% >1%

As a Green Chemist what do you need to consider about this process?

More Guided Group Discussion

From here, the 12 Principles were introduced . . .

Pointed out that our goal is to eliminate the distinction between a “chemist” and a “green chemist”


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.

General Model for Subsequent Lectures

Example:An Efficient and green protocol for the preparation of cycloalkanols: a practical synthesis of venlafaxine. Tetrahedron Letters 2004, 45, 7291-7295

N

OMe

O

OMe

OH

N

+10% aq. NaOH

TBAHSO4


1. 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?

3. 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?

Provided Thought Questions as a Guide to Reading Literature


• Group workExample: 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

Other Aspects of the Course


Presentation Requirements

• PowerPoint Presentation

• At least 15 minutes with 5 minutes for questions

• Incorporate a Green Chemistry product or process

• Comparative and Evaluative

• Accurately cited—no 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 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


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 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.”


Conclusions

• Experimental or non-traditional academic periods are especially amenableto 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 ofthe course.

• Suggestions for improvement: semester long course and the incorporation ofa lab.

Overall—Feedback was positive!


Acknowledgments

Green Chemistry In Education Workshop 2004 at the University of OregonJim HutchinsonKen DoxseeJulie HaackLallie Cobb McKenzieKristi MikkelsenDavid Brown Davidson CollegeRich Gurney Simmons College

Amy Cannon University of Massachusetts-Boston

Pfizer Global ManufacturingBuzz CueRich WilliamsLaurie St. Pierre BerryFrank SistareCarlos MojicaKurt Stickley

Wellesley College


Shelley, Jess, Kate, Maggie, Rachel, Erika, Chikoti, Nooshin, Christina and Mimosa

The Students!

D. Wicht Green Chemistry at Wellesley College August 2 nd, 2006 Green Chemistry at Wellesley...

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