Design of a Design of a Green Industrial Green Industrial Organic Chemistry Course Organic Chemistry Course Dr. Rabago Smith Dr. Rabago Smith Dr. Aurandt Dr. Aurandt Kettering University Kettering University CH 3 Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl O P S O O O O S O O P O O S NO 2 O O O O O O H H O O Cl Cl Cl Cl Green Chemistry & Engineering Conference Green Chemistry & Engineering Conference June 23, 2009 June 23, 2009
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Microsoft PowerPoint - paper69214_5.ppt [Read-Only] [Compatibility
Mode]Organic Chemistry CourseOrganic Chemistry Course
Dr. Rabago SmithDr. Rabago Smith Dr. AurandtDr. Aurandt
Kettering UniversityKettering University
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••Why?Why? ••AtAt thethe NationalNational ResearchResearch
Council,Council, environmentalenvironmental leadersleaders
agreedagreed thatthat greengreen chemistrychemistry mustmust bebe
incorporatedincorporated intointo thethe undergraduateundergraduate
engineeringengineering curriculumcurriculum.. ••ByBy usingusing
anan existingexisting coursecourse wewe reducedreduced thethe
strainstrain onon anan alreadyalready packedpacked
curriculumcurriculum..
Design of a Green Industrial Organic Chemistry CourseDesign of a
Green Industrial Organic Chemistry Course
GoalGoal
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3.3. IntegrationIntegration ofof thisthis coursecourse intointo
Kettering’sKettering’s curriculumcurriculum
4.4.AssessmentAssessment andand EvaluationEvaluation
5.5.DisseminationDissemination
Design of a Green Industrial Organic Chemistry CourseDesign of a
Green Industrial Organic Chemistry Course
ImplementationImplementation
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ObjectiveObjective 11:: RecognizeRecognize thethe majormajor
functionalfunctional groupsgroups presentpresent inin
organicorganic compoundscompounds..
ObjectiveObjective 22:: NameName thethe importantimportant
classesclasses ofof organicorganic chemicalschemicals
includingincluding:: alkanes,alkanes, alkenes,alkenes,
alkynes,alkynes, aromatics,aromatics, alcohols,alcohols,
amines,amines, aldehydes,aldehydes, ketonesketones andand
carboxyliccarboxylic acidsacids..
Design of a Green Industrial Organic Chemistry CourseDesign of a
Green Industrial Organic Chemistry Course
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Objective 3:Objective 3: Understand the general relationships
between the structure of Understand the general relationships
between the structure of organic materials and their physical
properties including organic materials and their physical
properties including melting point, boiling point, and
solubility.melting point, boiling point, and solubility.
ObjectiveObjective 44:: IdentifyIdentify thethe importantimportant
chemicalchemical reactionsreactions thatthat organicorganic
materialsmaterials undergoundergo includingincluding
addition,addition, elimination,elimination,
substitution,substitution, oxidationoxidation andand
reductionreduction..
ObjectiveObjective 55:: UnderstandUnderstand thethe originsorigins
andand usesuses ofof importantimportant feedstockfeedstock
chemicalschemicals usedused forfor industrialindustrial
synthesessyntheses ofof fuels,fuels, lubricants,lubricants,
consumerconsumer productsproducts andand polymerspolymers..
ObjectiveObjective 66:: BeBe familiarfamiliar withwith
chemicalschemicals;; physicalphysical andand
instrumentalinstrumental methodsmethods usedused toto
analyzeanalyze andand identifyidentify organicorganic
materialsmaterials..
Design of a Green Industrial Organic Chemistry CourseDesign of a
Green Industrial Organic Chemistry Course
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••LaboratoryLaboratory exerciseexercise ••NetworkingNetworking
opportunityopportunity ••ClassClass waswas divideddivided inin
twotwo modulesmodules
••ModuleModule 11 taughttaught byby DrDr.. AurandtAurandt
••ModuleModule 22 taughttaught byby DrDr.. RabagoRabago
SmithSmith
Design of a Green Industrial Organic Chemistry CourseDesign of a
Green Industrial Organic Chemistry Course
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Design of a Green Industrial Organic Chemistry CourseDesign of a
Green Industrial Organic Chemistry Course
ModuleModule 11 ••TwelveTwelve principlesprinciples ofof greengreen
chemistrychemistry andand thethe sixsix principlesprinciples ofof
greengreen engineeringengineering throughthrough
applicationapplication ofof pollutionpollution preventionprevention
throughthrough thethe lifecyclelifecycle ofof aa productproduct..
•• WeWe introducedintroduced organicorganic chemistrychemistry
compoundscompounds andand theirtheir physicalphysical
propertiesproperties..
RelevantRelevant activitiesactivities ••ToxicToxic ReleaseRelease
InventoryInventory (EPA)(EPA).. TheThe studentsstudents
choosechoose aa regionregion andand identifyidentify thethe
organicorganic compoundscompounds releasedreleased.. ••TheyThey
thenthen drawdraw lineline angleangle formulasformulas andand
structuralstructural formulasformulas forfor thethe
compound,compound, toto reinforcereinforce thethe skillsskills
learnedlearned inin classclass.. ••NameName thethe
compoundscompounds.. ••InvestigateInvestigate whywhy thesethese
compoundscompounds areare listedlisted onon thethe TRITRI..
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Design of a Green Industrial Organic Chemistry CourseDesign of a
Green Industrial Organic Chemistry Course
TRI Exercise: FormativeTRI Exercise: Formative
“I“I thoughtthought thatthat thethe toxictoxic releaserelease
inventoryinventory waswas aa veryvery goodgood
assignmentassignment.. ItIt openedopened mymy eyeseyes asas toto
whatwhat isis beingbeing pollutedpolluted inin mymy ownown
areaarea......TheThe resultsresults werewere veryvery
surprisingsurprising..”” “I“I thinkthink usingusing thethe
toxictoxic releaserelease inventoryinventory reallyreally
enlightenenlighten studentsstudents justjust howhow easyeasy itit
toto findfind outout whatwhat kindkind ofof chemicalchemical isis
beingbeing releasedreleased inin thethe environmentenvironment..
TheThe moremore knowledgeableknowledgeable wewe areare ofof ourour
environmentenvironment andand whatwhat wewe areare doingdoing toto
it,it, thethe moremore likelylikely wewe areare toto protectprotect
itit..””
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Design of a Green Industrial Organic Chemistry CourseDesign of a
Green Industrial Organic Chemistry Course
ModuleModule 22 ••InIn thisthis modulemodule thethe
studentsstudents areare introducedintroduced toto thethe mainmain
sourcessources ofof environmentalenvironmental
pollutantspollutants.. ••IntroductionIntroduction toto thethe
pollutionpollution preventionprevention (P(P22)) conceptconcept..
••ApplicationApplication ofof greengreen chemistrychemistry inin
thethe synthesissynthesis ofof chemicalschemicals andand itsits
impactimpact inin thethe overalloverall decreasedecrease inin
thethe productionproduction ofof pollutantspollutants..
RelevantRelevant activitiesactivities ••ThreeThree
differentdifferent polymerspolymers andand theythey drawdraw thethe
angleangle lineline structurestructure forfor thethe eacheach ofof
thethe monomersmonomers.. ••TheyThey thenthen answeranswer aa
seriesseries ofof questionsquestions thatthat relaterelate toto
thethe costcost ofof thethe material,material,
environmentalenvironmental informationinformation (i(i..ee.. COCO22
footfoot print,print, biodegradable,biodegradable, etcetc..))
andand thethe chemicalchemical propertiesproperties ofof thethe
polymerpolymer..
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Design of a Green Industrial Organic Chemistry CourseDesign of a
Green Industrial Organic Chemistry Course
CESCES :: FormativeFormative
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Design of a Green Industrial Organic Chemistry CourseDesign of a
Green Industrial Organic Chemistry Course
Laboratory ExerciseLaboratory Exercise Synthesis of
BiodieselSynthesis of Biodiesel
HC
H2C
H2C
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Design of a Green Industrial Organic Chemistry CourseDesign of a
Green Industrial Organic Chemistry Course
AssessmentAssessment Assessment exams Assessment exams Knowledge
AssessmentKnowledge Assessment Assessment of teaching
techniquesAssessment of teaching techniques SII assessment of the
class by studentsSII assessment of the class by students SII
assessment of class by professorsSII assessment of class by
professors Teaching evaluationsTeaching evaluations
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Design of a Green Industrial Organic Chemistry CourseDesign of a
Green Industrial Organic Chemistry Course
Assessment ExamsAssessment Exams
30 questions multiple choice30 questions multiple choice
Each question addresses a learning objectiveEach question addresses
a learning objective
GivenGiven toto allall sectionssections ofof thethe
classclass
ResultsResults areare comparedcompared betweenbetween
sectionssections toto determinedetermine ifif learninglearning
objectivesobjectives werewere accomplishedaccomplished..
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Design of a Green Industrial Organic Chemistry CourseDesign of a
Green Industrial Organic Chemistry Course
Assessment ExamAssessment Exam
0 20 40
er ce
nt ag
e co
rre ct
a ns
w er
P er
ce nt
ag e
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ns w
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Design of a Green Industrial Organic Chemistry CourseDesign of a
Green Industrial Organic Chemistry Course
Knowledge AssessmentKnowledge Assessment 1.1. Able to recognize the
major functional groups Able to recognize the major functional
groups
present in organic compounds. present in organic compounds.
Answer:Answer:
1.1. Not at allNot at all 2.2. SomewhatSomewhat 3.3. CapableCapable
4.4. Very CapableVery Capable
2.2.AbleAble toto namename importantimportant classesclasses ofof
organicorganic chemicals,chemicals, includingincluding thethe
alkanes,alkanes, alkenes,alkenes, alkynes,alkynes,
aromatics,aromatics, alcohols,alcohols, amines,amines,
aldehydes,aldehydes, ketones,ketones, andand carboxyliccarboxylic
acidsacids
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Design of a Green Industrial Organic Chemistry CourseDesign of a
Green Industrial Organic Chemistry Course
Knowledge AssessmentKnowledge Assessment 3.3. AbleAble toto
understandunderstand thethe generalgeneral
relationshipsrelationships betweenbetween thethe
structurestructure ofof organicorganic materialsmaterials andand
theirtheir physicalphysical propertiesproperties includingincluding
meltingmelting point,point, boilingboiling point,point, andand
solubilitysolubility ..
4.4. AbleAble toto identifyidentify thethe importantimportant
chemicalchemical reactionsreactions thatthat organicorganic
materialsmaterials undergo,undergo, includingincluding
addition,addition, elimination,elimination,
substitution,substitution, oxidationoxidation andand
reductionreduction..
5.5. AbleAble toto understandunderstand thethe originsorigins
andand usesuses ofof importantimportant feedstockfeedstock
chemicalschemicals usedused forfor industrialindustrial
synthesessyntheses ofof fuels,fuels, lubricants,lubricants,
consumerconsumer products,products, andand polymerspolymers..
6.6. FamiliarFamiliar withwith chemical,chemical,
physical,physical, andand instrumentalinstrumental methodsmethods
usedused toto analyzeanalyze andand identifyidentify organicorganic
materialsmaterials
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Design of a Green Industrial Organic Chemistry CourseDesign of a
Green Industrial Organic Chemistry Course
Knowledge assessment analysisKnowledge assessment analysis
1 2 3 4 5 6
0
20
40
60
80
Comparison of the evaluation assessment Comparison of the
evaluation assessment and the knowledge assessmentand the knowledge
assessment
P er
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co rr
0 20
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Design of a Green Industrial Organic Chemistry CourseDesign of a
Green Industrial Organic Chemistry Course
Evaluation assessment analysisEvaluation assessment analysis
Traditional sections (2)Traditional sections (2) Green sectionGreen
section
Comparison of the evaluation assessment with other
sectionsComparison of the evaluation assessment with other sections
P
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10
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60
70
80
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Design of a Green Industrial Organic Chemistry CourseDesign of a
Green Industrial Organic Chemistry Course
Assessment of ActivitiesAssessment of Activities 35 students35
students
DidDid thethe ToxicToxic ReleaseRelease InventoryInventory
exerciseexercise informinform youyou ofof thethe commoncommon
chemicalchemical namesnames ofof pollutantspollutants inin thethe
areaarea youyou chose?chose?
NotNot atat allall 00%% SomewhatSomewhat 5151..44%%
DefinitelyDefinitely 4848..66%%
DidDid thethe ToxicToxic ReleaseRelease InventoryInventory
exerciseexercise aidaid inin youryour understandingunderstanding
ofof thethe identificationidentification ofof functionalfunctional
groupsgroups inin chemicalchemical compounds?compounds?
NotNot atat allall 55..77%% SomewhatSomewhat 7171..44%%
DefinitelyDefinitely 2222..99%%
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Design of a Green Industrial Organic Chemistry CourseDesign of a
Green Industrial Organic Chemistry Course
CES SoftwareCES Software
NotNot atat allall 22..99%% SomewhatSomewhat 4545..77%%
DefinitelyDefinitely 5151..44%%
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Design of a Green Industrial Organic Chemistry CourseDesign of a
Green Industrial Organic Chemistry Course
SIISII StrengthsStrengths
InsightInsight “It“It isis interestinginteresting howhow muchmuch
chemistrychemistry affectsaffects thethe restrest ofof
engineering,engineering, oror anyany otherother partpart ofof
thethe world”world”
ImprovementsImprovements More examplesMore examples Moves too
fastMoves too fast To much informationTo much information
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Design of a Green Industrial Organic Chemistry CourseDesign of a
Green Industrial Organic Chemistry Course
44..3535 onon aa 55 pointpoint scalescale
CommentsComments:: “The“The classclass waswas veryvery
interestinginteresting andand openedopened mymy mindmind toto
organicorganic chemistrychemistry andand itsits
applicationsapplications..”” “This“This coursecourse reallyreally
makesmakes youyou thingthing aboutabout whatwhat kindkind ofof
productsproducts you'reyou're usingusing andand whatwhat theythey
mightmight bebe doingdoing toto thethe environmentenvironment..
ItIt waswas veryvery interestinginteresting andand actuallyactually
funfun..””
Teaching EvaluationsTeaching Evaluations
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Design of a Green Industrial Organic Chemistry CourseDesign of a
Green Industrial Organic Chemistry Course
Questions? Questions?
AcknowledgmentsAcknowledgments
Funded by the Michigan DEQ RETAP Internship Program Environment
Science Funded by the Michigan DEQ RETAP Internship Program
Environment Science and Service Divisionand Service Division
ConclusionsConclusions ••The design and implementation of a Green
Industrial The design and implementation of a Green Industrial
Organic Chemistry was successfulOrganic Chemistry was
successful
••The data obtained proves that the learning objectives The data
obtained proves that the learning objectives for the class can be
successfully learned after a “green for the class can be
successfully learned after a “green spin” is added to the
classspin” is added to the class
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Design of a Green Industrial Organic Chemistry CourseDesign of a
Green Industrial Organic Chemistry Course
Extra slidesExtra slides
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Design of a Green Industrial Organic Chemistry CourseDesign of a
Green Industrial Organic Chemistry Course
PrePre--test assessment analysistest assessment analysis
Traditional sections (2)Traditional sections (2) Green sectionGreen
section
Comparison of the evaluation assessment with other
sectionsComparison of the evaluation assessment with other sections
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Design of a Green Industrial Organic Chemistry CourseDesign of a
Green Industrial Organic Chemistry Course Syllabus
comparisonSyllabus comparison
WeekWeek Topic/ Green CourseTopic/ Green Course Topic Traditional
courseTopic Traditional course
11 Syllabus, Introductions, Syllabus, Introductions, Assessment
testAssessment test Role of Organic Chemistry and the Role of
Organic Chemistry and the
EnvironmentEnvironment
Molecules Molecules
22
Role of Organic Chemistry and the Role of Organic Chemistry and the
EnvironmentEnvironment
Introduction to Functional Groups (TRI Introduction to Functional
Groups (TRI exercise)exercise)
AlkanesAlkanes
Alkenes and Alkynes Alkenes and Alkynes
33 AlkanesAlkanes AlkenesAlkenes
Alkenes and Alkynes Alkenes and Alkynes Reactions of Alkenes
Reactions of Alkenes
44 Alkene ReactionAlkene Reaction Green ChemistryGreen Chemistry
Alcohols Alcohols
Exam 1Exam 1 Benzene and Its Derivatives Benzene and Its
Derivatives
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Design of a Green Industrial Organic Chemistry CourseDesign of a
Green Industrial Organic Chemistry Course Syllabus
comparisonSyllabus comparison
WeekWeek Topic/ Green CourseTopic/ Green Course Topic Traditional
courseTopic Traditional course
55 AlcoholsAlcohols Aldehydes Ketones Carboxylic AcidsAldehydes
Ketones Carboxylic Acids
Fossil Fuels & Petroleum Refining Fossil Fuels & Petroleum
Refining
Alternative Fuels Alternative Fuels
66
CES SoftwareCES Software EXAM 1 (Module 1)EXAM 1 (Module 1)
Introduction to organic contaminants Introduction to organic
contaminants
in the environmentin the environment
Alcohols, Ethers, Phenols, and Thiols Alcohols, Ethers, Phenols,
and Thiols
Carboxylic Acids Carboxylic Acids
77 Introduction to organic contaminants Introduction to organic
contaminants in the environmentin the environment Carboxylic Acids
Carboxylic Acids
88 Petrochemical contamination of the Petrochemical contamination
of the
environmentenvironment 12 Principles of green chemistry12
Principles of green chemistry
Exam 2Exam 2
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Design of a Green Industrial Organic Chemistry CourseDesign of a
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Syllabus comparisonSyllabus comparison
1010 Case StudyCase Study Exam Module 2Exam Module 2 Laboratory
exerciseLaboratory exercise
Organic Polymer ChemistryOrganic Polymer Chemistry
Exam 3Exam 3