Ethanol and Education: 1 0 0 w 9.f Alcohol as a Theme for 8 1 1 5- 1 Teaching Chemistry 0 2 k- b 1/ 2 0 1 0. 1 oi: d 5 | 1 0 2 5, 1 e n u J b): e W e ( at D n o ati c bli u P In Ethanol and Education: Alcohol as a Theme for Teaching Chemistry; Barth, et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2015. 1 0 0 w 9.f 8 1 1 5- 1 0 2 k- b 1/ 2 0 1 0. 1 oi: d 5 | 1 0 2 5, 1 e n u J b): e W e ( at D n o ati c bli u P In Ethanol and Education: Alcohol as a Theme for Teaching Chemistry; Barth, et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2015. 1189 ACS SYMPOSIUM SERIES Ethanol and Education: Alcohol as a Theme for Teaching Chemistry 1 00 Roger Barth, Editor w 9.f West Chester University 8 1 5-1 West Chester, Pennsylvania 1 0 2 bk- Mark A. Benvenuto, Editor 1/ 2 0 University of Detroit Mercy 1 0. 1 Detroit, Michigan oi: d 5 | 1 0 2 5, 1 e n u J b): e W e ( at D n o ati Sponsored by the c ubli ACS Division of Chemical Education P AmericanChemicalSociety,Washington,DC DistributedinprintbyOxfordUniversityPress In Ethanol and Education: Alcohol as a Theme for Teaching Chemistry; Barth, et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2015. LibraryofCongressCataloging-in-PublicationData Ethanolandeducation:alcoholasathemeforteachingchemistry/RogerBarth,editor, WestChesterUniversity,WestChester,Pennsylvania,MarkA.Benvenuto,editor, UniversityofDetroitMercy,Detroit,Michigan;sponsoredbytheACSDivisionof ChemicalEducation. 1 pagescm.-- (ACSsymposiumseries;1189) 0 0 Includesbibliographicalreferencesandindex. w 9.f ISBN978-0-8412-3059-0(alk.paper) 18 1. Alcohols.2. Brewing--Studyandteaching.3. Chemistry--Studyandteaching. 1 5- 4. Chemistry,Analytic--Studyandteaching. I.Barth,Roger,editor.II.Benvenuto, 1 0 MarkA.(MarkAnthony)editor.III.AmericanChemicalSociety.Divisionof 2 k- ChemicalEducation. b 1/ QD305.A4E752015 2 0 540.71--dc23 1 0. 2015015889 1 oi: d 5 | 1 0 2 5, 1 e ThepaperusedinthispublicationmeetstheminimumrequirementsofAmericanNational n u Standard for Information Sciences—Permanence of Paper for Printed Library Materials, J b): ANSIZ39.48n1984. e W e ( Copyright©2015AmericanChemicalSociety at D n DistributedinprintbyOxfordUniversityPress o ati c AllRightsReserved. ReprographiccopyingbeyondthatpermittedbySections107or108 ubli oftheU.S.CopyrightActisallowedforinternaluseonly,providedthataper-chapterfeeof P $40.25plus$0.75perpageispaidtotheCopyrightClearanceCenter,Inc.,222Rosewood Drive,Danvers,MA01923,USA.Republicationorreproductionforsaleofpagesinthis bookispermittedonlyunderlicensefromACS.Directtheseandotherpermissionrequests toACSCopyrightOffice,PublicationsDivision,115516thStreet,N.W.,Washington,DC 20036. Thecitationoftradenamesand/ornamesofmanufacturersinthispublicationisnottobe construedasanendorsementorasapprovalbyACSofthecommercialproductsorservices referenced herein; nor should the mere reference herein to any drawing, specification, chemicalprocess, orotherdataberegardedasalicenseorasaconveyanceofanyright or permission to the holder, reader, or any other person or corporation, to manufacture, reproduce,use,orsellanypatentedinventionorcopyrightedworkthatmayinanywaybe relatedthereto. Registerednames,trademarks,etc.,usedinthispublication,evenwithout specificindicationthereof,arenottobeconsideredunprotectedbylaw. PRINTEDINTHEUNITEDSTATESOFAMERICA In Ethanol and Education: Alcohol as a Theme for Teaching Chemistry; Barth, et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2015. Foreword The ACS Symposium Series was first published in 1974 to provide a mechanism for publishing symposia quickly in book form. The purpose of the series is to publish timely, comprehensive books developed from the ACS sponsoredsymposiabasedoncurrentscientificresearch. Occasionally,booksare developed from symposia sponsored by other organizations when the topic is of 1 0 0 keeninteresttothechemistryaudience. w 9.f 18 Beforeagreeingtopublishabook,theproposedtableofcontentsisreviewed 1 5- forappropriateandcomprehensivecoverageandforinteresttotheaudience. Some 1 0 2 papersmaybeexcludedtobetterfocusthebook;othersmaybeaddedtoprovide k- b comprehensiveness. When appropriate, overview or introductory chapters are 1/ 02 added. Draftsofchaptersarepeer-reviewedpriortofinalacceptanceorrejection, 1 0. andmanuscriptsarepreparedincamera-readyformat. 1 oi: 5 | d As a rule, only original research papers and original review papers are 01 included in the volumes. Verbatim reproductions of previous published papers 2 5, arenotaccepted. 1 e n u J b): e W ACSBooksDepartment e ( at D n o ati c bli u P In Ethanol and Education: Alcohol as a Theme for Teaching Chemistry; Barth, et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2015. Preface Thisbookcomesfromthesymposium“ChemistryofFermentedBeverages” at the Biennial Conference on Chemical Education (BCCE) that was held in GrandRapids,MichiganinAugustof2014. Wehavenonethelesscastawidenet, including several distinguished chemists who did not present in Grand Rapids. The symposium and book address some wonderful opportunities to engage 1 0 0 students in a wide variety of chemistry classes, field experiences, study abroad, pr 9. andotherlearningactivitiesthroughexamplesinvolvingalcoholicbeverages. The 8 11 topiclendsitselftotreatmentsthatrangefromserioustoquirkyandlight-hearted, 5- 1 depending on the audience and objectives. Every subdiscipline of chemistry 0 2 k- can be addressed through alcoholic beverages. All levels, from introductory b 1/ chemistry for non-science majors to advanced chemistry seminars and research 2 10 canincorporatethescienceofalcoholicbeverages. Thisvolumewillcoversome 0. 1 of the possibilities through the lens of the experiences of chemistry faculty who doi: teachaboutalcoholicbeveragesinavarietyofsettings, rangingfromtraditional 5 | chemistryprogramstotechnicalprogramsinthealcoholindustry. 1 0 2 Tosome,thisprojectmayseemstrange;wegetasmatteringofamusedlooks, 5, 1 raised eyebrows, and sly chuckles. But there is nothing strange about reaching e un studentswithchemistrythatintereststhem. Whetherwewanttoadmititornot, J b): alcohol consumption is a big part of the lifestyle of many students, so it makes e W senseforfacultymemberstoteachchemistryclassesthatrevolvearoundalcohol, ate ( orthatusealcoholicbeveragestomakesomepointinachemistryclass. Alcoholic D n fermentation may be the oldest chemical process mastered by humankind. The o ati negative consequences of excessive drinking are well-known, yet numerous c bli studies have pointed out the health benefits of mild to moderate regular alcohol u P consumption. Giventhelargepercentageofstudentswhoregularlydrinkalcohol, ofteninviolationofinstitutionalprohibitionandagerestrictions,theyshouldhave accesstothesciencebehindthebeverage,aswellassomeintelligentdiscussion about it. Within this volume there are some very good chapters covering alcohol, its production, analysis, metabolism, as a source of livelihood, its role in the development of chemistry, and as a means of attracting student interest. The authors draw from experiences at every level from introductory chemistry for non-majors,throughgeneralandadvancedchemistrymajorcoursesandprojects, tospecializedbusiness/industrialapplications. Allofthemshowhowsomeaspect ofalcoholcanbeusedasamodeltoenhancethelearningprocess. Thisvolume will provide resources for faculty who are considering, developing, or actively teaching: ix In Ethanol and Education: Alcohol as a Theme for Teaching Chemistry; Barth, et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2015. ▪ Acourseorsequenceonalcoholproductionorservice; ▪ A stand-alone course based on fermented beverage chemistry or biotechnology; or ▪ Alcohol-based lessons or examples for an existing chemistry or biochemistrycourse. In addition, chemists who are interested in beer, wine, or spirits, and who would like to be able to field questions about alcoholic beverages and their chemistry, whether from students in a class, or from friends and colleagues in somelessformalsetting,willbenefitfromthisbook. We extend heartfelt thanks to the many persons whose efforts greatly enhancedthequalityofthisbook. TheseincludeACSBooksacquisitionseditor Tim Marney, and Letitia Glozer and Jasmine Suarez of Technica Editorial. 01 Marcy Barth (RB’s wife) professionally redrew and redesigned several of the 0 pr illustrations. Specialthanksgoestomorethanthirtyanonymousreviewers,whose 9. 18 outstandingworkensuredtheaccuracyandclarityofeachchapter. Wethankour 1 5- familiesandouruniversitieswhoseconstantsupportmadeourworkpossible. 1 20 We have approached the topic quite seriously, but have tried not to take k- b ourselves too seriously in the process. And so, concerning what is within these 1/ 02 pages, drinkitallin! 1 0. 1 oi: d 5 | Roger Barth 1 0 DepartmentofChemistry 2 5, WestChesterUniversity 1 ne WestChester,Pennsylvania19383 u b): J [email protected](e-mail) e 610-436-3210(telephone) W e ( 610-436-2890(fax) at D n o ati c ubli MarkA.Benvenuto P DepartmentofChemistryandBiochemistry UniversityofDetroitMercy Detroit,Michigan48221-3038 [email protected](e-mail) 313-993-1184(telephone) 313-993-1144(fax) x In Ethanol and Education: Alcohol as a Theme for Teaching Chemistry; Barth, et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2015. Editors’ Biographies Roger Barth RogerBarthwasborninNewYorkCity,attendedpublicschoolsinLevittown, PA, and was awarded a bachelor’s degree in chemistry from La Salle College in Philadelphia and a doctorate in physical chemistry from the Johns Hopkins University in Baltimore. He did post-doctoral work on heterogeneous catalysis 1 0 0 at Drexel University and at University of Delaware. His current research is on ot 9. beer chemistry. Barth has been a faculty member at West Chester University in 8 1 1 Pennsylvaniasince1985. Hisbook, TheChemistryofBeer: TheScienceinthe 5- 01 Suds,waspublishedbyWileyin2013. 2 k- b 1/ 2 0 0.1 Mark A. Benvenuto 1 oi: 5 | d Mark Benvenuto is a Professor of Chemistry at the University of Detroit 1 Mercy, in the Department of Chemistry & Biochemistry. His research spans 0 2 5, many subjects, including energy dispersive X-ray fluorescence spectroscopy to 1 e determine trace elemental compositions of aquatic and land-based plant matter, n u J food and dietary supplements, and medieval and ancient artifacts. Benvenuto b): receivedaB.S.inchemistryfromtheVirginiaMilitaryInstitute,andafterseveral e W e ( yearsintheArmy,aPh.D.ininorganicchemistryfromtheUniversityofVirginia. at Afterapost-doctoralfellowshipatThePennsylvaniaStateUniversity, hejoined D n thefacultyattheUniversityofDetroitMercyin1993. o ati c bli u P ©2015AmericanChemicalSociety In Ethanol and Education: Alcohol as a Theme for Teaching Chemistry; Barth, et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2015. Chapter 1 Overview Ethanol and Education: Alcohol as a Theme for Teaching Chemistry 1 RogerBarth*,1andMarkA.Benvenuto2 0 0 h c 9. 8 1DepartmentofChemistry,WestChesterUniversity, 1 5-1 WestChester,Pennsylvania19383 1 0 2DepartmentofChemistryandBiochemistry,UniversityofDetroitMercy, 2 bk- Detroit,Michigan48221-3038 1/ 2 *E-mail: [email protected]. 0 1 0. 1 oi: d 5 | 1 0 2 5, 1 e Fermented beverages have been in use since early prehistory. n u J Fermentation itself as well as the processes before and after it eb): all have important chemical implications. The subdisciplines W e ( of chemistry play significant roles in the preparation, quality, at and packaging of fermented beverages. Several key concepts D n in chemistry and related technical disciplines have origins in o ati fermentedbeverageproduction. c bli u P Introduction Although the alcoholic beverage industry cultivates an image of traditional craftsmanship passed down the generations, it is in fact a highly technical endeavor. Production processes are constantly refined for efficiency, quality, andconsistency. Eachstepisrichinchemistry, engineering, andbiotechnology. Eachoffersopportunitiesforstudentstolearnaboutaspectsofchemistry. Every subdiscipline of chemistry is heavily represented. Because of its relevance and its ability to arouse student interest, teaching about the chemistry of fermented beveragesisbecomingmorewidespreadinhighereducation. ©2015AmericanChemicalSociety In Ethanol and Education: Alcohol as a Theme for Teaching Chemistry; Barth, et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2015. History Alcohol goes back to the origins of humanity. It seems likely that when modern humans crossed the Red Sea from Africa to Asia, they were already equipped with the skills to ferment sugary liquids to alcoholic beverages (1). Chemicalevidenceforthedeliberateproductionofalcoholicbeveragesdatesfrom 9000yearsagoinNeolithicChina(2). Evidenceforgrapewineisreporteddating atleast7000yearsagointhenorthernMesopotamianregion(3),butsincegrapes originate at least 500 km to the north, it is likely that wine is actually older (4). Barleybeerhasbeenfounddatingfrom5500yearsago,alsointheMesopotamian region (5). When the invention of writing opened the book on history 5000 yearsago,beerwasalreadydistributedthroughouttheMesopotamiansociety(6). Distillation came much later. It was mentioned by Abu Musa Jabir ibn Hayyan 01 “Geber” (721-815), an ancient chemist from the Moslem golden age whose 0 ch writingsinfluencedtheteachingandpracticeofchemistryforcenturies. Distilled 9. 18 beveragescameintoregularuseinGermanyinthelate1400’s(7). 1 5- Theproductionofalcoholicbeverageshasbeenadrivingforceforchemistry 1 20 fromitsoriginsasascience. AntoineLavoisier(1743-1794),inwhoseanalytical k- b balance chemistry took its modern form, described the fermentation reaction as 1/ 02 grapemust=carbonicacid+alcohol. Lavoisieristheauthorofthefirstmodern 1 0. chemistrytextbook(8). Thefascinationwithalcoholicfermentationandalcoholic 1 oi: beverages has not subsided; a search for “alcoholic beverage” on the Amazon® d 5 | booksiteturnsup22,898results. 1 0 2 5, 1 e n u b): J Classification of Alcoholic Beverages e W e ( All alcoholic beverages are produced by fermentation of simple sugars by at D microorganisms,mostcommonlyayeast,Saccharomycescerevisiaeoroneofits n o closerelatives,S.uvarumorS.pastorianus. Amajorclassificationiswhether,the ati c alcoholissignificantlyconcentrated, eitherbydistillationorfreezing. Asecond bli u major classification is the source of sugar for fermentation. The sugar can be P providedbyanaturalsourceofsugar,suchasfruit,honey,orsugarcane,oritcan derivefromthehydrolysisofstarch. Amyriadofsecondarydistinctionsemerge whenpost-processes,suchasadditionofflavorsoraginginbarrelsareconsidered. Non-ConcentratedBeverages Thekeydistinctioninthisclassofbeveragesisthetypeofthecarbohydrate, sugarorstarch. Someexamplesofnon-concentratedbeveragesderivedfromsugar aregiveninTable1. Therearemanyflavoredandhybridvarieties,eachwithits ownname,andoftenmorethanonename. 2 In Ethanol and Education: Alcohol as a Theme for Teaching Chemistry; Barth, et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2015.