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ACS SYMPOSIUM SERIES 1011 Green Chemistry Education g or s. c a s. b u p 9, 2009 | http://09-1011.fw001 Changing the Course of Chemistry 10 n October 1021/bk-2 Paul TY.a Ale nUanisvtearssit,y Editor N o10. HEoi: Irvin J. Levy, Editor ENC09 | d Gordon College V MU22, 20 HE UNIe: April KatAhmreyrinca nE C. hPemaircealn Sto,c iEetdy itor Cat SD NIn CHatio TEblic d by Pu e d a o nl w o D Sponsored by the ACS Division of Chemical Education, Inc. American Chemical Society, Washington, DC In Green Chemistry Education; Anastas, P., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2009. g or s. c a s. b u p 9, 2009 | http://09-1011.fw001 10 October 21/bk-2 n 10 N o10. ISBN: 978-0-8412-7447-1 HEoi: ENC09 | d NThaeti opnaaple rS utasnedda ridn thfoisr pInufbolricmaatitioonn m Seceitesn tchees —miPneirmmuamne rnecqeu iroefm Penaptse ro ff oAr mPerirnicteadn V MU22, 20 Library Materials, ANSI Z39.48-1984. HE UNIe: April CDoisptyrirbiguhtetd © b y2 0O0x9f oArdm eUrniciavne rCsihteym Pirceassl Society Cat SD All Rights Reserved. Reprographic copying beyond that permitted by Sections NIn TECHblicatio tC1h0lae7ta roaa rn pc1ee0r -8c Choaefpn tttheeerr , UfeI.enS c.o. ,C f o2$p24y20r .i2gR5h ot psAeluwcsto io$sd0 a .7lDl5o rwipveeerd, fpoDarga einn vtieesrr snp,aa li Mdu stAeo ot0hn1el9y C2, 3po,rp oUyvriSidgAehdt. d by Pu Republication or reproduction for sale of pages in this book is permitted only e under license from ACS. Direct these and other permission requests to ACS d oa Copyright Office, Publications Division, 1155 16th Street, N.W., Washington, wnl DC 20036. o D The citation of trade names and/or names of manufacturers in this publication is not to be construed as an endorsement or as approval by ACS of the commercial products or services referenced herein; nor should the mere reference herein to any drawing, specification, chemical process, or other data be regarded as a license or as a conveyance of any right or permission to the holder, reader, or any other person or corporation, to manufacture, reproduce, use, or sell any patented invention or copyrighted work that may in any way be related thereto. Registered names, trademarks, etc., used in this publication, even without specific indication thereof, are not to be considered unprotected by law. PRINTED IN THE UNITED STATES OF AMERICA In Green Chemistry Education; Anastas, P., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2009. g or s. c a s. Dedication b u p 9, 2009 | http://09-1011.fw001 To the educators who are 10 October 21/bk-2 by adcvhanacninggin ggre tehne p rcioncuiprslees oanf cdh permacitsictersy n 10 N o10. HEoi: NC9 | d E0 V MU22, 20 HE UNIe: April Cat SD NIn CHatio TEblic d by Pu e d a o nl w o D In Green Chemistry Education; Anastas, P., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2009. Foreword g or s. c a s. b u The ACS Symposium Series was first published in 1974 to pro­ p 9, 2009 | http://09-1011.fw001 pvoseuipdarerepdc o has.f e rm oOomecfc c htaAhaseniC oissnSmea rl silepfysoo ,r nb issopo outrokeb dsl pi sauhsrbeyil nmidgspeh svo ytesimlimoap peobelysdai,s aefc rdoqo mumoip cnrsk eylchymu eprnirnose isnvbitaeo ossbkpco oioefnoknsrstomi rfde.i ecd vT erbhelye­­ 10 October 21/bk-2 oauthdeire nocreg. anizations when the topic is of keen interest to the chemistry N on 10.10 Before agreeing to publish a book, the proposed table of con­ HEoi: tents is reviewed for appropriate and comprehensive coverage and for NC9 | d interest to the audience. Some papers may be excluded to better focus the E0 V MU22, 20 bapoporko; proiathtee,r s ovmearvy iebwe oar ddinetdr odtou ctporroyv icdhea pcteorms praereh enasdidveedn.e sDs.r afWts heonf HE UNIe: April mchaanputesrcsr ipatrse arpee eprr-erpeavrieedw eidn cparmioerr at-or eafdinya l foarcmceapt.t ance or rejection, and Cat SD As a rule, only original research papers and original review NIn CHatio papers are included in the volumes. Verbatim reproductions of previ­ TEblic ously published papers are not accepted. d by Pu e d a o nl ACS Books Department w o D In Green Chemistry Education; Anastas, P., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2009. Preface Any book that strives to describe the current status of a dynamic g or field does so at its peril. So it is with this book. The field of green s. ac chemistry is among the most dynamic in science, with a rate of growth s. ub and adoption that is not only remarkable but also necessary for our p 9 | http://11.pr001 cpirvoiglrizeassti oon f ttoh e acghreieevn e chsuemstaisitnrayb imlitoyv. emAenn t esiss enthtiea l sueclceemses nto f ing retehne 00 chemistry education, which provides an understanding of the scientific 01 9, 209- challenges faced by green chemistry, mastery of the techniques of green 10 October 021/bk-2 cchheemmiisctarly ,p raancdt icgee,n ienrasil gahdt vianntoc etmhee natp polfi cthaeti ofnie oldf. thIne tphrei nacbispelensc eo fo gf rteheins on 0.1 educational component, green chemistry cannot achieve its promise and HEN doi: 1 potential. NC9 | Practitioners of green chemistry education, including those UE200 represented in the chapters in this book, are showing both the leadership V M22, and the diversity of approaches needed to advance green chemistry. UNIApril Many of the contributors to this volume have taken part in a series of SCHE Date: Csyhmempoicsiaal oSno cgieretye n (AchCeSm)i sotrvye r edthuec atcioounr sceo nodfu csteevde rbayl AtheC SA nmaetiroicnaanl TECHNIblication cmheeemtiinsgtrsy iant 2a0l0l 7l eavnedls 2a0n0d 8t.h Crouurgrhenout ta papllr ofaacchetess otof cihnecmoripsotrrya teidnug cgarteioenn d by Pu have been documented and discussed. The achievements of both the e contributors to this book and the broader chemical education community d a nlo to date in regard to green chemistry education have been driven by w o pedagogical insights into new and effective ways to teach chemistry as D well as by student interest—often in the form of passionate demand—for exposure to green chemistry. The only thing more impressive than the accomplishments in the field of green chemistry education thus far is the field's seemingly limitless future potential to accomplish the following: xi In Green Chemistry Education; Anastas, P., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2009. attracting students to the field of chemistry who otherwise may never have seen themselves as potential chemists or even as scientists providing chemists with an essential skill set that will be needed as the basis of a sustainable world bringing a new generation of innovators to engage some of the greatest challenges our society and our civilization face today. This book has been published in the sincerest hope that it will g or catalyze the efforts of future educators to build on the work that has s. c s.a already been accomplished and thereby help green chemistry education b pu attain new heights. http://pr001 9 | 11. 00 01 In Appreciation: 9, 209- 10 October 021/bk-2 extraordTinhairsy ebfofookrt s woof ulmd y htwavoe coneodt itobrse,e nM sp.o sKsaibthlery n wPitahroeuntt atnhde on 0.1 Professor Irv Levy. In addition, we all thank each of the authors for their HEN doi: 1 contributions that are the essence of this volume. NC9 | UE200 SCHE UNIV MDate: April 22, CPSceahnuoteolr l Tfoof.r FGAorrneeesantrs yCt ahanesdm Eisntrvyi raonndm Gerneteanl SEtnugdiiense ering Chemistry NIon Chemical Engineering Department d by TECH Publicati NYeawle HUanviveenr,s iCtyT 06520 e d a o nl w o D xii In Green Chemistry Education; Anastas, P., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2009. Chapter 1 Changing the Course of Chemistry Paul T. Anastas and Evan S. Beach g or cs. Center for Green Chemistry and Green Engineering, Chemistry, School a bs. of Forestry and Environmental Studies, Chemical Engineering Department, u 9, 2009 | http://p09-1011.ch001 Yale University, New Haven, CT 06520 10 October 021/bk-2 Tish ea ne duecvaetri-oenv oolfv cihnegm einstdse aanvdo ra ltlo th okseee pin teurpe stwedit hi n tchhee mlaistetrsyt on 0.1 innovations, discoveries, concepts, perspectives and tech­ ENCHEN 09 | doi: 1 nrdeiecqseuignents yooeff a trhcse h eifsmi eltidhc.ea lO dpnerevo edoluof cptthmse e amnnto dso tf p erGxoccrieetseisnneg s C dhethveaemtl oisrpetmrdyue cn- ets t hoiner UNIV MUApril 22, 20 esGelriemekesinn atCote h petrmhoeiv sitdgryee niaennrt aoto itvohnee r cvohiefe wmt oiosxtfir cyt h cesuu rbarspitcpaurnlocuaemcsh. besyT hhtoiisg hblcuihgilahdptiitnnegrg HE e: some of the outstanding work in the field. Cat SD CHNIation TEblic d by Pu e Introduction d a o nl w o The path that the field of chemistry has taken over the course of the past 200 D years is one of creativity, innovation, and discovery. It is also a path that we as chemists have followed without fully considering the consequences of either what we have created or the methods and processes we have used to do so. This is largely due to the fact that historically we have had little understanding of the impact of chemicals on human health and the environment. In recent decades, science has dramatically increased our knowledge of the various types of adverse consequences of chemicals. More importantly, it has begun to provide us with a molecular-level understanding of these consequences, thereby allowing us to design our chemical products and transformation processes in order to minimize © 2009 American Chemical Society 1 In Green Chemistry Education; Anastas, P., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2009. 2 these adverse consequences. This is the basis of the green chemistry movement, which has been bringing about a wide range of innovations throughout the chemical enterprise. It is generally accepted that if the still-nascent field of green chemistry is going to have the impact required to allow chemists to play their central role in designing a safer, healthier, and more sustainable world, we must teach the next generation of scientists and educated citizens the fundamental framework of green chemistry. This volume highlights some of the outstanding work from the green chemistry education community that is dedicated to charting this new org course. s. c a s. b u p 9, 2009 | http://09-1011.ch001 the kIeny Ttfroahcdeuit siW.o nCaalhy ec mhTeihsmtasi cta arCle ehedneucmcoautirisoatgnre,y dt eHtcoha nasic chAailel vwpee arcfyloesrvm Bearn eccehene m hTaicsa autle gntrhdaentd s fotorm bae­ October 1021/bk-20 thdiaeozsncasrr idbu esodirn gic noa ntnesyer mqrusee qnoucfie r.ae tdo mEell eeegmcaoennnctoesm ioynn, s sytthneetph epesceisor inooodrm iccy h,t eahmbaliezc aarwld ip,t rhao mcleiotstuslneest reoisgf arwradra eslttyoe on 0.1 generated, feedstock use, or other impacts of the chemistry beyond the effects on HEN doi: 1 yield and purity of the target product. Chemists have been taught to accept the NC9 | fact that handling of explosive, toxic, carcinogenic, or otherwise risky materials UE200 is simply part of the nature of the profession. Nonchemists who attend V M22, introductory chemistry lectures and labs are unlikely to see any challenge to the UNIApril gpeoniseoranls .p erRceedptuicoinn go fr icshke, mwishtircyh asis thdee frienaeldm aosf afi rfeusn, cetxiopnlo soifo nbso, tph olhlauztaiordn , aanndd CHE ate: exposure, is almost always achieved by minimizing exposure. In teaching CHNISation D hlaoboodrsa,t odrieepse,n dtheinsc etr aonnsl apteerss oton alr elpiraontceec tiovne ceaqpuiitpaml-e annt,d sutrpickte espa-fientyte ntsriavien infgu mtoe TEblic avoid injury, and adoption of microscale experiments to limit the amounts of d by Pu dangerous reagents used. To students, the origin of chemical reagents is largely e a mystery, and likewise, little thought is given to what happens to the materials d a nlo poured into the hazardous waste collection jars at the end of every experiment. w o Green chemistry education seeks to enhance chemists' understanding of the D impacts of their design choices and experiments. Curricula based on the 12 Principles of Green Chemistry (/) cast the field of chemistry in an entirely different light. Hazard and waste become recognized as design flaws or, more positively, as opportunities for innovation (2). Experiments can be performed in laboratories that are more comfortable and inviting as well as more economical to maintain. Routine handling of inherently safe chemicals reinforces the beneficial impacts and problem-solving potential of the chemical enterprise. Students gain an appreciation for product lifecycles (3) and environmental ethics and are empowered to follow their moral inclinations as scientists and engineers (4). In Green Chemistry Education; Anastas, P., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2009. 3 Introduction of Green Chemistry as a Field The idea of green chemistry was initially developed as a response to the Pollution Prevention Act of 1990, which declared that U.S. national policy should eliminate pollution by improved design (including cost-effective changes in products, processes, use of raw materials, and recycling) instead of treatment and disposal. Although the U.S. Environmental Protection Agency (EPA) is known as a regulatory agency, it moved away from the "command and control" or "end of pipe" approach in implementing what would eventually be called its g or "green chemistry" program. By 1991, the EPA Office of Pollution Prevention s. ac and Toxics had launched a research grant program encouraging redesign of s. ub existing chemical products and processes to reduce impacts on human health and p 9, 2009 | http://09-1011.ch001 ttCFhhoheeu anleeldaenranvltgyiiro eo n1nA 9m(9wNe0ansSr.t dF. s)T tihhnTee hn1 ei9 n p9tEr6roo PcddeArueec wdtiein oda n tpt teaoonr fttnf iutoehnnresd ht aoibpn ab nsouiwctah ilt rheaP screatehadsereic dmheU inci.t nSiaa .ngl dNrGe aeirnnteid eocunnh saCetlrm hiaSeilsmc tgireirysne tecrinnye 10 chemistry success stories. The Awards program and the technologies it October 021/bk-2 hTihgeh lmigihdt-st oa-rlea tne ow19 9a0 cso srnawer satonn ein corfe athsee ginre tehne cnhuemmbiestrr yo fe dinutceartnioatniaoln caul rmriceuetliunmgs. on 0.1 devoted to green chemistry, such as the Gordon Research Conferences on Green HEN doi: 1 Chemistry, and green chemistry networks developed in the United States, the NC9 | United Kingdom, Spain, and Italy. The 12 Principles of Green Chemistry were UE200 published in 1998, providing the new field with a clear set of guidelines for V M22, further development (/). In 1999, the Royal Society of Chemistry launched its CHE UNIate: April jjpooruuorrlnnifaaellr sa,t Geadrne,d e sngp reecCeinha elc mihsiessmutreiyss. t rdye vcIonot necdthe ept ots lgahrsaetv een1 c0co hnyetmeinairusset,rd y nthoaa tgivoaeni naa lpt rpaneceattriweodno .r kinsA mchalaejvoaerr SD CHNIation asiwganr doefd t htios wCahsa upvrionv, idGerdu bbbys t,h aen dci tSactihorno cfokr, wthhe ic2h0 0c5o mNmobeenld Pedri zthee fior r wCohrekm aiss t"rya TEblic great step forward for green chemistry" (5). d by Pu e d a o nl Green Chemistry in the Classroom w o D The increasing acceptance of green chemistry in the last decade has been paralleled by the rapid development of green chemistry educational programs around the world, mostly at the undergraduate and graduate levels. Classes are offered by many institutions, ranging from small four-year colleges to major research universities. The first college-level course in green chemistry was taught by Professor Terry Collins at Carnegie Mellon University (CMU) (d). Since 1992, the course has been offered to graduate students and advanced undergraduates. In 2008, the course objectives were as follows: In Green Chemistry Education; Anastas, P., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2009. 4 To understand sustainability ethics as they apply to chemistry and establish the arguments for recognizing "green" criteria. To reflect on motives and forces that have entrenched technologies that are obviously or potentially harmful to the environment (7). To define "green chemistry", place its development in a historical context, introduce the 12 Principles, and study successful examples of green technologies. To identify the key challenges facing green chemistry and consider what will be required to solve them (8). g or To identify reagents, reactions, and technologies that should be and s. ac realistically could be targeted for replacement by green alternatives. s. ub To understand the history, meaning, and importance of persistent and p 9, 2009 | http://09-1011.ch001 befTinieoovl adibcrseo cconuomfmm peueunl batfaltaiilcmv a ehin leidpaa orlh tlehwlua ialtttanhhnd tlt sehs auraedsnatiandtsig n. earnebsdieloiactryrci hsnc eii endn gicsrere.ue pnt ocrhse mwihsitcryh apnrde stehnet remlaatjeodr 10 October 021/bk-2 rTehael- wcoourlrds ei mstpraecstsse so ft hceh elminiks tsb' edtweseiegnn cfuhnodicaemse. nFtaol r cehxeammipclael, bcoonndce-dpitss soacnida titohne on 0.1 energy is taught in the context of ozone depletion, flame retardants, and HEN doi: 1 bleaching technologies; substitution and elimination reactions are discussed in NC9 | terms of their role in the persistence of organochlorine pollutants in the UE200 environment. This link between molecular structure and hazard is discussed in V M22, depth in Chapter 8. Sustainability ethics is also a significant component of the HE UNIe: April ceoxuprasned. thTehire dmesaitgenr iacla phaabs ilbiteieens idne ovredloerp etdo eton sushreo wth atht en enwe ecdh efmori ccahle mpriosdtsu cttos Cat and processes will better consider and incorporate the interests of future SD CHNIation ginetnreordauticoinnsg (s8tu, de9n).t s tAo noetnhdeor criimnep-odritsarnutp tisnegc tiocnh emofi cathlse tchoaut rsien tefrofceures es wiotnh TEblic cellular processes at environmental concentrations and represent a major design d by Pu challenge for green chemists. Historical case studies, including cultural de reactions to chemistry as well as tensions among industry, the environmental a nlo community, and public health professionals, are covered in detail. As the course w o at CMU moves well into its second decade, it is evolving to take advantage of D web technology. Lecture materials will soon be available freely to the global green chemistry community. Furthermore, the course web site is envisioned to become a venue where students, teachers, and experts can interact in problem- solving activities and discussions of state-of-the-art green chemistry research. At the cutting edge of green chemistry curricula for chemists is the emergence of new molecular design principles (Chapter 8). As green chemistry continues to mature and incorporate learning from a variety of disciplines, courses in the field will provide students with better tools for understanding the molecular bases of acute and chronic toxicity, endocrine-disrupting properties, In Green Chemistry Education; Anastas, P., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2009.

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