Chemical Education Today
Reports from Other Journals
News from Online: Green Chemistry by Erich S. Uffelman
Developing environmentally benign chemical products and processes within the context of renewable resources defines the field of Green Chemistry for many of its practioners. The impetus to pour more and more federal and private funds into this relatively new area of research has come from the realization that we may “run out of environment” faster than we run out of specific natural resources (http://www.sciam.com/ a r t i c l e . c f m ? a r t i c l e I D = 0 0 0 A 8 E C 8 - 0 F 7 6 - 1 FA 8 807883414B7F0000&chanID=sa006&colID=12). Green chemistry is inextricably linked with energy issues, environmental issues, and the rapidly developing field of environmental economics. This is a brief overview of some Web sites that readers new to green chemistry might find useful. The American Chemical Society has a fine Web site devoted to green chemistry at http://www.chemistry.org/portal/a/ c/s/1/acsdisplay.html?DOC=education\greenchem\index.html; links to many useful resources and Web sites may be found there. Additionally, what might be described as the twelve commandments of green chemistry stated by Anastas and Warner (1) are crisply summarized on the Web site and quoted below: 1. Prevention: It is better to prevent waste than to treat or clean up waste after it has been created. 2. Atom Economy: Synthetic methods should be designed to maximize the incorporation of all materials used in the process into the final product. 3. Less Hazardous Chemical Syntheses: Wherever practicable, synthetic methods should be designed to use and generate substances that possess little or no toxicity to human health and the environment. 4. Designing Safer Chemicals: Chemical products should be designed to effect their desired function while minimizing their toxicity. 5. Safer Solvents and Auxiliaries: The use of auxiliary substances (e.g., solvents, separation agents) should be made unnecessary wherever possible and innocuous when used. 6. Design for Energy Efficiency: Energy requirements of chemical processes should be recognized for their environmental and economic impacts and should be minimized. If possible, synthetic methods should be conducted at ambient temperature and pressure. 7. Use of Renewable Feedstocks: A raw material or feedstock should be renewable rather than depleting whenever technically and economically practicable. 8. Reduce Derivatives: Unnecessary derivitization (use of blocking groups, protection/deprotection, temporary modification of physical/chemical processes) should be minimized or avoided if possible, because such steps require additional reagents and can generate waste.
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9. Catalysis: Catalytic reagents (as selective as possible) are superior to stoichiometric reagents. 10. Design for Degradation: Chemical products should be designed so that at the end of their function they break down into innocuous degradation products and do not persist in the environment. 11. Real-time Analysis for Pollution Prevention: Analytical methodologies need to be further developed to allow for real-time, in-process monitoring and control prior to the formation of hazardous substances. 12. Inherently Safer Chemistry for Accident Prevention: Substances and the form of a substance used in a chemical process should be chosen to minimize the potential for chemical accidents, including releases, explosions, and fires.
The Environmental Protection Agency’s Web site at http:// www.epa.gov/greenchemistry/ has many valuable links and resources and is the resident site for the Presidential Green Chemistry Challenge Awards; it lists the winners of the awards since the program began in 1996. The Web site for past winners at http://www.epa.gov/greenchemistry/ past.html#2003 has abstracts for all of the research awards online, and provides a quick survey of important accomplishments and research areas in green chemistry. In addition to covering the Presidential Green Chemistry Challenge Awards, Chemical & Engineering News regularly runs articles on green chemistry drawn from conferences, meetings, and policy forums; the Web addresses for three recent articles are http://pubs.acs.org/isubscribe/journals/cen/81/ i39/html/8139sci2.html, http://pubs.acs.org/isubscribe/journals/ cen/80/i47/html/8047sci1.html, and http://pubs.acs.org/cen/ coverstory/8020/8020green.html. The journal Green Chemistry (http://www.rsc.org/is/journals/current/green/greenpub.htm) is sponsored by the Royal Society of Chemistry and features research articles by specialists in the discipline. The Royal Society of Chemistry’s Green Chemistry Network page (http://www.chemsoc.org/networks/ gcn/) is a terrific site with a comprehensive set of relevant links and other information. Our Canadian neighbors have a useful site, the Canadian Green Chemistry Network, at http:// www.greenchemistry.ca. Implementing Green Chemistry in the Curriculum For readers interested in implementing green chemistry in their educational curricula, powerful justification may be found in an article by Terrence Collins in Science (http:// w w w. s c i e n c e m a g . o r g / c g i / c o n t e n t / f u l l / 2 9 1 / 5 5 0 1 / 48?maxtoshow=&HITS=10&hits=10&RESULTFORMAT= &author1=Collins%2C+T&searchid= 1069599196208_2167&stored_search= &FIRSTINDEX=0&fdate=10/1/1995&tdate=11/30/2003). In
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Chemical Education Today
Reports from Other Journals
World Wide Web Addresses Relating to Green Chemistry
the Journal of Chemical Education, “green chemistry” is a keyword that can be used to search for pertinent articles (http:// www.jce.divched.org/Journal/Search/index.html); there is a feature column edited by Mary M. Kirchhoff as well. The University of Scranton has developed a powerful set of green chemistry modules for use across the entire chemistry curriculum, from general chemistry through advanced courses in all areas, with funding from the Camille and Henry Dreyfus Foundation (http://academic.scranton.edu/faculty/ CANNM1/dreyfusmodules.html). Readers interested in guiding their undergraduates to internships in environmental issues can visit Washington and Lee University’s Environmental
Studies Web site at http://environmentalstudies.wlu.edu/ internships.htm; the site provides a wealth of information on many national and international opportunities, in addition to those local to Lexington, VA. Educational Institution Sites Major programs in green chemistry are housed at many U.S. universities. Some of these are listed. The Center for Environmentally Beneficial Catalysis is a newly funded $17 million NSF Engineering Research Center that involves the University of Kansas, the University of Iowa, and Washing-
http://www.nottingham.ac.uk/supercritical/
General Treatment
http://www.sciam.com/article.cfm?articleID=000A8EC80F76-1FA8-07883414B7F0000&chanID=sa006&colID=12
http://www.chemistry.org/portal/a/c/s/1/ acsdisplay.html?DOC=education\greenchem\index.html
http://web.chem.monash.edu.au/GreenChem/ http://www.rsc.org/is/journals/current/green/greenpub.htm Energy Management
http://www.doe.gov/engine/ content.do?BT_CODE=ENVIRONMENT
http://www.chemsoc.org/networks/gcn/ http://www.greenchemistry.ca
http://alsos.wlu.edu/
EPA
http://www.epa.gov/greenchemistry/
http://www.ornl.gov/sci/csd/Research_areas/ csdresearch.html
http://www.epa.gov/greenchemistry/past.html#2003
http://auto.howstuffworks.com/hydrogen-economy.htm
ACS Chemical and Engineering News Articles
http://pubs.acs.org/isubscribe/journals/cen/81/i39/html/ 8139sci2.html http://pubs.acs.org/isubscribe/journals/cen/80/i47/html/ 8047sci1.html http://pubs.acs.org/cen/coverstory/8020/8020green.html Implementing Green Chemistry in the Curriculum
http://www.sciencemag.org/cgi/content/full/291/5501/ 48?maxtoshow=&HITS=10&hits=10&RESULTFORMAT=&author1= Collins%2C+T&searchid=1069599196208_2167&stored_search= &FIRSTINDEX=0&fdate=10/1/1995&tdate=11/30/2003 http://www.jce.divched.org/Journal/Search/index.html http://academic.scranton.edu/faculty/CANNM1/ dreyfusmodules.html http://environmentalstudies.wlu.edu/internships.htm
http://www.naturallydangerous.com http://www2.exxonmobil.com/Corporate/Notebook/ Footprint/Corp_N_FootprintDetails.asp http://www.chevrontexaco.com/social_responsibility/ environment/ Chemical Industry Dow http://www.dow.com/environment/ehs.html DuPont http://www1.dupont.com/NASApp/dupontglobal/corp/ index.jsp?GXHC_gx_session_id_=602239ac3418e24e&GXHC_lang= en_US&GXHC_ctry=US&page=/content/US/en_US/social/ SHE/index.html Merck http://www.merck.com/about/cr/policies_performance/ environmental/ Bayer http://www.bayer.com/en/bayer/gv_sustain.php
Research
http://www.ku.edu/~cebc/ http://www.nsfstc.unc.edu/
http://www.cbsnews.com/stories/2003/11/13/60minutes/main583528.shtml
http://www.chem.cmu.edu/groups/collins/
http://www.americanchemistry.com/
http://www.uoregon.edu/~hutchlab/greenchem/index.html http://www.york.ac.uk/res/gcg/welcome.htm http://www.le.ac.uk/chemistry/greenchem/index.html
The access date for all sites is November 2003.
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Environmental Economics
http://yosemite.epa.gov/ee/epa/eed.nsf/pages/homepage
http://lnweb18.worldbank.org/ESSD/envext.nsf/ 44ByDocName/EnvironmentalEconomicsandIndicators http://europa.eu.int/comm/environment/enveco/
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ton University in St. Louis; see http://www.ku.edu/~cebc/. The NSF Science and Technology Center for Environmentally Responsible Solvents and Processes involves Georgia Institute of Technology, North Carolina A&T State University, North Carolina State University, University of North Carolina, Chapel Hill, and The University of Texas, Austin; see http:// www.nsfstc.unc.edu/. The Institute for Green Oxidation Chemistry is at Carnegie Mellon University (http:// www.chem.cmu.edu/groups/collins/). The University of Oregon also has a green chemistry program; see http:// www.uoregon.edu/~hutchlab/greenchem/index.html. Many university programs abroad focus on green chemistry; a few are listed. The University of York, England not only has a significant program in green chemistry (http://www.york.ac.uk/ res/gcg/welcome.htm), but also is the host for the RSOC site mentioned above. The University of Leicester (http:// www.le.ac.uk/chemistry/greenchem/index.html) and the University of Nottingham (http://www.nottingham.ac.uk/supercritical) are also obviously British sites. The Centre for Green Chemistry, located at Monash University, Australia, is a special research center funded by the Australian Research Council (http://web.chem.monash.edu.au/GreenChem). These U.S. and international university Web sites not only discuss their research contributions to the field of green chemistry, they also often have useful material that introduces their work to nonspecialist audiences and provides links to other good Web sites. Energy Management U.S. Government agencies involved in green chemistry beyond the EPA- and NSF-sponsored sites mentioned above include the DOE, with its legacy of energy management and nuclear waste cleanup issues (http://www.doe.gov/engine/ content.do?BT_CODE=ENVIRONMENT). More information on the chemistry of nuclear waste cleanup (and a comprehensive treatment of nuclear issues in general) may be found at Alsos Digital Library for Nuclear Issues, the NSFsponsored National Science Digital Library project at Washington and Lee University (http://alsos.wlu.edu/). Oak Ridge National Laboratory also obviously has interests in these areas, and their Web site at http://www.ornl.gov/sci/csd/Research_areas/ csdresearch.html has considerable useful information. Since energy concerns are intimately tied to green chemistry, discussions of the hydrogen economy are important to the field. A good, balanced discussion of the hydrogen economy, including its green and non-green aspects, may be found at http://auto.howstuffworks.com/hydrogen-economy.htm. For trenchant observations on energy and environmental issues, see James P. Collman’s Web site at http:// www.naturallydangerous.com. For industrial positions on renewable energy and the environmental impact of energy production, the Web sites of Exxon-Mobil at http:// www2.exxonmobil.com/Corporate/Notebook/Footprint/ Corp_N_FootprintDetails.asp and Chevron-Texaco at http:// www.chevrontexaco.com/social_responsibility/environment/, make for fascinating reading, particularly given that the Exxon Valdez accident occurred prior to the Exxon-Mobil merger. www.JCE.DivCHED.org
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Sites of the Chemical Industry Many Web sites of chemical industries do not discuss their green chemistry issues separately from their overall environmental policy and environmental research interests. Representative examples of the information available online on industrial approaches to this topic include Dow (http:// www.dow.com/environment/ehs.html), DuPont (http:// www1.dupont.com/NASApp/dupontglobal/corp/index.jsp? GXHC_gx_session_id_=602239ac3418e24e&GXHC_lang= en_US&GXHC_ctry=US&page=/content/US/en_US/social/ SHE/index.html), Merck (http://www.merck.com/about/cr/ policies_performance/environmental/), and Bayer (http:// www.bayer.com/en/bayer/gv_sustain.php). Within the Dow Web site, the Environmental Health and Safety Debates and Dilemmas section might be of particular interest to teachers who want to initiate class discussions on topics of industrial relevance. The site features issues of industrial concern, with the regulatory, legal, and economic implications involved mentioned and with links to more information on the areas. Because Dow acquired Union Carbide after the legal settlement of the Bhopal, India, disaster, Dow’s corporate issues involving this topic are worth reading and considering. Whether chemists approve or disapprove, the Bhopal disaster is now connected in the minds of some news reporters to the threat of terrorism to the chemical industry. Anastas and Warner published their 12 commandments of green chemistry (1) prior to the September 11, 2001 terrorist attacks against the U.S. Green chemistry principle number 12, (inherently safer chemistry should be chosen to prevent accidents, including releases, explosions, and fires) can now be thought of as a green chemistry contribution to minimizing terrorist targets. For one example of how this has been spotlighted in the mass media, see the recent (November 14, 2003) report on the CBS News 60 Minutes Web site summarizing their televised episode on the topic (http:// w w w. c b s n e w s . c o m / s t o r i e s / 2 0 0 3 / 1 1 / 1 3 / 6 0 m i n u t e s / main583528.shtml). For information from the American Chemistry Council (featured in the 60 Minutes story), see their Web site, which also has a wealth of information on other green chemistry and environmental topics pertinent to chemical industry (http://www.americanchemistry.com/). Environmental Economics To a significant extent the impetus for green chemistry depends on how much the environment is valued, since much (though certainly not all) of the research in the area is intended to replace chemicals and chemical processes that, if environmental damage is not considered of any importance, are highly successful. Consequently, it is useful to have some knowledge of the rapidly emerging field of environmental economics and the debates and issues within that field. For the U.S. EPA’s information and positions in this area, see http://yosemite.epa.gov/ee/epa/eed.nsf/pages/homepage. For the European Union’s information and positions in this area, see http://europa.eu.int/comm/environment/enveco/. For the World Bank’s information and positions in this area, see
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morial Trust. My pedagogical research is in the area of developing undergraduate experiments in NMR spectroscopy and green chemistry (2).
Conclusion Finally, green chemistry and its related issues are so huge in scope that in an article of this brevity I have of necessity left out a multitude of worthy and interesting Web sites, and I apologize in advance for those omissions. Green chemistry and its related issues can also become politically charged, so I have endeavored to provide a set of Web sites that, taken together, present what I hope is a fairly balanced overview. My own interests and experiences in this area are stated below.2 Notes 1. The Presidential Green Chemistry Challenge Awards are given for innovation in the areas of alternative synthetic pathway development, alternative solvents and reaction conditions, safer chemical design, academic research, and small business. 2. I received a Ph.D. in 1992 from the California Institute of Technology. I was a Ph.D. student under Terrence J. Collins at Caltech and Carnegie Mellon from 1984–1991. I spent two years as an NIH Postdoctoral Fellow in James P. Collman’s group at Stanford University. When Collins won the 1999 Presidential Green Chemistry Challenge Award, I received a Certificate of Merit for initiating the TAML Catalytic Oxidant project within his group. I currently do research in green oxidation catalysis that has been partially funded over the years by the National Science Foundation, the American Chemical Society–Petroleum Research Fund, Research Corporation, Hewlett-Packard, and the Jeffress Me-
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Literature Cited 1. Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: New York, 1998; p 30. 2. (a) Uffelman, E. S.; Cox, E. H.; Davis, C. M.; Goehring, J. B.; Lorig, T. An NMR-Smell Module for the First Semester General Chemistry Laboratory. J. Chem. Educ. 2003, 80, 1368–1372. (b) France, M. B.; Uffelman, E. S. Ring-Opening Metathesis Polymerization with a Well-Defined Ruthenium Carbene Complex: An Experiment for the Undergraduate Inorganic or Polymer Laboratory. J. Chem. Educ. 1999, 76, 661–665. (c) Uffelman, E. S.; Doherty, J. R.; Schulze, C.; Burke, A. L.; Bonnema, K.; Watson, T. T.; Lee, D. W., III. Microscale Syntheses, Reactions, and 1H-NMR Spectroscopic Investigations of Square Planar Macrocyclic Tetraamido-N Cu(III) Complexes Relevant to Green Chemistry. J. Chem. Educ. 2004, 81, 182–185. (d) Uffelman, E. S.; Doherty, J. R.; Schulze, C.; Burke, A. L.; Bonnema, K.; Watson, T. T.; Lee, D. W., III. Microscale Syntheses, Reactions, and 1HNMR Spectroscopic Investigations of Square Planar Macrocyclic Tetraamido-N Co(III) Complexes Relevant to Green Chemistry. J. Chem. Educ., in press.
Erich S. Uffelman is in the Department of Chemistry, Washington and Lee University, Lexington, VA 24450;
[email protected].
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