In the Classroom
Bringing State-of-the-Art, Applied, Novel, Green Chemistry to the Classroom by Employing the Presidential Green Chemistry Challenge Awards Michael C. Cann Department of Chemistry, University of Scranton, Scranton, PA 18510;
[email protected] Most chemistry courses involve general concepts and theories but little if any time is spent discussing current stateof-the-art and innovative practices of the chemical industry, academic and other institutions, especially practices that are directed toward pollution prevention (green chemistry) (1). Most science majors graduate with little appreciation or understanding of industrial chemical processes and even less of such state-of-the-art processes that are green. As a means of bringing state-of-the-art, applied, novel green industrial chemistry into the classroom, we have employed a discussion (poster presentation and ad hoc classroom) of the awardwinning Presidential Green Chemistry Challenge (PGCC) Awards Program entries as part of our Environmental Chemistry course. Background On March 16, 1995, President Clinton announced the Presidential Green Chemistry Challenge (2). This program endeavors to “promote pollution prevention and industrial ecology through a new EPA Design for the Environment partnership with the chemical industry”. This is a part of the Clinton–Gore administration’s efforts at the EPA Reinventing Environmental Regulations Initiative and these awards are the only presidential-level awards made specifically in chemistry. Individuals, groups, and organizations are invited to nominate green chemistry technologies that are an example of one or more of the following three focus areas (as excerpted from the 1999 PGCC Awards Program Nominations Package). 1. The use of alternative synthetic pathways for green chemistry, such as: Catalysis/biocatalysis. Neutral processes, such as photochemistry and biomimetic synthesis. Alternative feedstocks that are more innocuous and renewable (e.g., biomass). 2. The use of alternative reaction conditions for green chemistry, such as: Use of solvents that have a reduced impact on human health and the environment. Increased selectivity and reduced wastes and emissions. 3. The design of chemicals that are, for example, Less toxic than current alternatives. Inherently safer with regard to accident potential.
It is also important to note that the application for PGCC awards must contain a “statement affirming that the green chemistry technology has been demonstrated, implemented, and/or applied in the United States within the last five years”. Thus, although these technologies are novel and significant, they are not “pie in the sky” proposals, as they
have been proven through demonstration and many have recently been put into practice. In 1996 and 1997 approximately 70 proposals were submitted for these awards, while in 1998 the number jumped to 120, indicating an increasing awareness of the importance of green chemistry and the prestige associated with these awards. The EPA publishes, in addition to the winners, brief summaries of all proposals submitted each year (3), providing an excellent database for noteworthy accomplishments in the area of green chemistry (4). Awards are made each year in each of the three focus areas above, to a small business and to an academic institution. These awards are made during the Annual Green Chemistry and Engineering Conference at the National Academy of Sciences (normally held in June of each year). The titles and institutions of the award-winning submissions for 1996, 1997, and 1998 are as follows. 1996 1. The Catalytic Dehydrogenation of Diethanolamine. Monsanto Company. (Diethanolamine is a key intermediate in the production of Monsanto’s Roundup herbicide and this new synthetic pathway produces less waste, gives a higher yield, and eliminates the need for the use of cyanide and formaldehyde.) 2. The Development and Commercial Implementation of 100 Percent Carbon Dioxide as an Environmentally Friendly Blowing Agent for the Polystyrene Foam Sheet Packaging Market. The Dow Chemical Company. (Carbon dioxide has been used to replace ozonedepleting blowing agents such as CFCs and HCFCs.) 3. Designing an Environmentally Safe Marine Antifoulant. Rohm and Haas Company. (Sea–Nine antifoulant prevents fouling from a wide variety of marine organisms; however, because it degrades rapidly it has no chronic toxicity, thus causing no harm to nontarget organisms). 4. Production and Use of Thermal Polyaspartic Acid. Donlar Corporation. (A very efficient synthesis of thermal polyaspartic acid was developed.) 5. Conversion of Waste Biomass to Animal Feed, Chemicals, and Fuels. Mark Holtzapple, Texas A&M University.
1997 1. The BHC Company Ibuprofen Process: Innovation in Pharmaceutical Processing. BHC Company. (This process is a new synthetic pathway that offers 80% atom utilization, compared to other pathways, which offer at best 40% atom utilization.) 2. Revolutionary Wet Processing Technology Which Removes Photoresist and Organic Contaminants for the Semiconductor, Flat Panel Display and Micromachining Industries Using Only Water and Oxygen as Raw Materials Eliminating the Need for Sulfuric Acid, Hydrogen Peroxide or Ashers. Legacy Systems Inc.
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In the Classroom 3. Reducing Risks to Human and Environmental Health with a New Class of Antimicrobial Chemistry. Albright & Wilson Americas Inc. (A new biocide was developed that has an unusually low toxicity toward higher species and degrades rapidly in the environment to harmless substances.) 4. Design and Application of Surfactants for Carbon Dioxide. Joseph M. DeSimone, University of North Carolina at Chapel Hill. (Surfactants specific to carbon dioxide were developed to facilitate the use of carbon dioxide as a solvent in industrial and chemical processes.) 5. Dry View Technology (a photothermographic film). Imation Corporation. (Photothermographic films are processed without the need for fixers or developers, thus eliminating the need for many toxic chemicals.)
1998 1. The Use of Microbes as Environmentally-Benign Synthetic Catalysts. Karen M. Draths and John W. Frost, Michigan State University. (Microbes created by genetic manipulation are employed as synthetic catalysts for the conversion of glucose into commodity and fine chemicals.) 2. The Development of the Concept of Atom Economy. Barry Trost, Stanford University. 3. Technology for the Third Millennium: The Development and Commercial Introduction of an Environmentally Responsible Fire Extinguishment and Cooling Agent. PYROCOOL Technologies Inc. 4. Elimination of Chlorine in the Synthesis of 4Aminodiphenylamine: A New Process Which Utilizes Nucleophilic Aromatic Substitution for Hydrogen. Flexsys America L. P. (4-Aminodiphenylamine is a key intermediate in the synthesis of rubber antidegradants.) 5. Novel Membrane-Based Process for Producing Lactate Esters—Nontoxic Replacements for Halogenated and Toxic Solvents. Argonne National Laboratories. 6. Invention and Commercialization of a New Chemical Family of Insecticides Exemplified by CONFIRM Selective Caterpillar Control Agent and the Related Selective Insect Control Agents MACH and INTREPID. Rohm and Haas Company.
The PGCC Poster Presentation In the fall semester at the University of Scranton we offer a course in Environmental Chemistry. This course is required for our students majoring in Environmental Science but it may also be taken as an elective by Chemistry, Biochemistry, and Biology majors. The prerequisites for this course are two semesters of General Chemistry and two semesters of Organic Chemistry. One requirement of Environmental Chemistry is the presentation of a poster detailing one of the PGCC winning proposals. At the beginning of the semester the instructor obtains from the EPA (3) copies of the winning proposals and a copy of “The Presidential Green Chemistry Challenge Awards Nominations Package”, which discusses the program and provides information to those who wish to apply. These are placed on reserve in the library and the students (in teams of two) read these materials and, on a first come–first served basis, select one of the proposals to present their poster on.
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Figure 1. Andrea Mugherini and Paul Bechtel are shown with their 1998 “best of show” award-winning poster. Their poster presented the work of Karen Draths and John Frost of Michigan State University entitled “The Use of Microbes as Environmentally-Benign Synthetic Catalysts”.
In preparation for the poster presentation the students must research the background of the proposal, including the prior state of the science/technology and how the subject of the proposal improves the science/technology, particularly from an environmental standpoint. In their search for information about the proposal the students are required to: 1. Converse with the contact person listed on the proposal and request further literature, including journal articles, patents, and industrial publications. Usually the students make contact by phone or email and they have found most individuals to be very helpful and eager to supply information. 2. Search the Web for information not only regarding the science/technology of the proposal but also regarding the company or institution submitting the proposal. 3. Search Chemical Abstracts (we use STN express).
During the course of the semester the teams must submit weekly progress reports. Several times during the semester the topics we are covering in class overlap with the subject matter of the PGCC proposals and this leads to some very interesting discussions, usually prompted by the students. This of course allows for some “real live” state-of-the-art and practical chemistry to be brought to the classroom. During the third week of November, the day before the oral presentation, the students set up their posters in the lobby of the chemistry–biology building. Thus many others, including faculty and students from other classes, are able to view the posters. The next evening each team of students gives a 15-minute oral presentation of their poster, which is followed by questions from the audience. The audience consists of the students enrolled in the class and the instructor. In addition, other students and faculty who are inspired to come as a result of viewing the posters in the lobby and by flyers announcing the poster session, are often in attendance. Lively discussions generally occur during the question period. After all presentations have been made the instructor asks, “Which of the posters should be given the ‘best of show award’”, and this also elicits a lively discussion (Fig. 1).
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In the Classroom
The grade for each student depends upon the following criteria: 1. Presentation of scientific content, both visual and verbal. 2. Visual effect: neatness, layout, professional manner, and impact. 3. Oral delivery. 4. Performance during the question period. 5. Did the student ask insightful and meaningful questions during the question period of the other students?
Other Uses for the PGCC Proposals For the first time this year, students in our Industrial Chemistry course (a required course for the Chemistry– Business major, taught by Trudy A. Dickneider) will also study the PGCC. Students in this course must write a report on one of the PGCC proposals, covering the chemistry/ technology, the motivation for the development of the project (save dollars, save in compliance costs, etc.), and the business aspects such as relation to profit and plant design. Many colleges and universities do not offer environmental chemistry or industrial chemistry courses and thus may not find these exercises applicable to their courses. However, the chemistry presented in the PGCC proposals covers a broad spectrum of areas in chemistry and thus the specific chemistry in a particular proposal might lend itself to discussion in many different courses. For example, The BHC Ibuprofen Process could be incorporated into a sophomore organic course during a discussion of any number of topics, including Friedel–Crafts acylation, formation and hydrolysis of epoxides, and hydrogenation of carbonyls to form alcohols.1 Conversion of Waste Biomass to Animal Feed, Chemicals and Fuels could be discussed in a biochemistry class under the guise of enzymes in microorganisms that hydrolyze cellulose and hemicellulose into free sugars. The Catalytic Dehydrogenation of Diethanolamine (this leads to a key intermediate in the synthesis of the herbicide Roundup) might be discussed in a synthetic organic class as an alternative synthetic pathway. The Production and Use of Thermal Polyaspartate Polymers lends itself to a discussion in polymer chemistry (and in biochemistry, since these polymers are biodegradable while polyacrylic acid is not). Reducing Risks to Human and Environmental Health with a New Class of Antimicrobial Chemistry offers itself for discussion in a toxicology class. A general discussion of the Presidential Green Chemistry Challenge Awards Program would also lend itself as a topic in courses dealing with environmental science or environmental studies for non-science majors.
Discussing The Presidential Green Chemistry Challenge Awards in courses not only brings “real live”, creative, stateof-the-art, and valuable chemistry to the students, but also environmentally sound chemistry. Industry is embracing green chemistry more and more, for it not only makes for a cleaner environment but it also makes for good public relations and perhaps most significantly (from industry’s viewpoint) it usually is beneficial to the bottom line (5). Students who are not exposed to green chemistry and taught to “think green” will be at a disadvantage. Note 1. I also teach sophomore organic and graduate mechanistic organic and have employed a discussion of this proposal in these courses.
Literature Cited 1. For a previous article on green chemistry in teaching and research see: Collins, T. J. J. Chem Educ. 1995, 72, 965–966. 2. Raber, L. Chem. Eng. News 1996, 74(Jul 15), 9–10. Raber, L. Chem. Eng. News 1997, 75(Jun 30) 7–8. Additional recent articles on green chemistry include: Breen, J. Chem. Eng. News 1997, 75(Dec 22), 47. Hileman, B. Chem. Eng. News 1998, 76(Jun 8), 31–32. 3. To obtain information on the PGCC proposals, contact Tracy Williamson at the EPA; phone: 202/260-3960; email: williamson.
[email protected]. We have found Dr. Williamson to be very helpful and enthusiastic regarding disseminating information on the PGCC awards and the program in general. Information available in print includes The PGCC Awards Program Nomination Package for 1999 Awards and The PGCC Awards Program Summary of 1997 [1996 is also available] Award Entries and Recipients. Much of the same information can be found on the Web at http://www. epa.gov/opptintr/gcc/. 4. Additional information on green chemistry can be found in the following ACS symposium volumes. Benign by Design: Alternative Synthetic Design for Pollution Prevention; Anastas, P. T.; Farris, C. T., Eds.; ACS Symposium Series 577; American Chemical Society: Washington, DC, 1994. Pollution Prevention in Industrial Processes: The Role of Process Analytical Chemistry; Breen, J. J.; Dellarco, M. J., Eds.; ACS Symposium Series 508; ACS, 1992. Designing Safer Chemicals: Green Chemistry for Pollution Prevention; Devito, S. C.; Garrett, R. L., Eds.; ACS Symposium Series 640; ACS, 1996. Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T.; Williamson, T. C., Eds.; ACS Symposium Series 626; ACS, 1996. 5. Wilkinson, S. L. Chem. Eng. News 1997, 75(Aug 4), 35-43. An editorial by then ACS President R. Breslow: Breslow, R. Chem. Eng. News 1996, 74(Aug 26), 72.
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