Introduction

Astheworldslowlyrunsoutofoil,thepeopleontheplanetneedtostartlookingforalternative
formsofenergy.Agoodsolutionforthisisbiodiesel.Biodieselusesoldwasteoilsandconvertthem
intousableformsofdiesel.Themainburdenofbiodieselisthecostofproductionitisstillrather
expensivetoproduce.Thefourprimarywaysofproducingbiodieselaredirectuseandblending,
microemulsions,thermalcracking,andtransesterification.
1
Anotherwaythatmanyscientistsaretryingto
createbiodieselisfrommicroalgae.Thegrowthrateofmicroalgaemakesiteasytocreatealarge
amountofusablemicroalgalbiodieselthatcanbecompetitivewithpetroleumdiesel.
2
Biodieselcanalso
becreatedusingsoybeansasthebase.Europeanbiodieselismainlymadefromrapeseedoil.Sincethe
UShasalargeamountofsoybeans,theindustrycanusesoybeansasaprimaryfeedstockforthe
biodiesel.
3

Thepurposeofthisexperimentistochangevegetableoilintousablebiodieselby
transesterificationoftriglycerideswithmethoxide.Thebiodieselismadebytransesterification.
Transesterificationisreactinganalcoholwithaglycerol.Thevegetableoilmayhave1840long
carboxylicacidsattachedtoglycerolatpotentiallydifferentsaturations.Thetriglyceridereactswith
methanoltoformestersandglycerol.Smalleralcoholsareusedbecauselargeralcoholsmayhaveissues
duetoaoverlylargestericfactorandmayalsoincreasethevolatilityofthebiodieselthatiscreated.
Therearefreefattyacidsthatneedtobebrokendown.Freefattyacidsarelongchainsof
carboxylicacidsthatfloataroundinsolutioninsteadofstickingtotheglycerol.Thesefattyacidsarenot
convertedandneedtoeitherbeneutralizedorchangedtoesters.Saponificationisusedtoneutralizethe
fattyacids.Thisisdonebyaddingsomebasetoseparateitthefattyacidsfromtheglycerol.Oneofthe
mostimportantthingsistokeepthesolutionawayfromwaterbecausethewaterwillhydrolyzethe
triglyceridestoformsoaps.Correctusageofthebalances,measuringusinggraduatedcylinders,and
quantitativetransferwillbeusedinthislab.

Reagent MolarMass
(g/mol)
Density
(g/mL)
Hazards
Vegetable
Oil
.918 Maycauseslightirritation
Methanol

32.04 .791 Hazardousincaseofskincontact(irritant),ofeyecontact

(irritant),ofingestion,ofinhalation.Slightlyhazardousin
caseofskincontact(permeator).Severeoverexposure
canresultindeath.
KOH 56.11 2.04 Veryhazardousincaseofskincontact(corrosive,irritant),
ofeyecontact(irritant,corrosive),ofingestion,of
inhalation.Theamountoftissuedamagedependsonlength
ofcontact.Eyecontactcanresultincornealdamageor
blindness.Skincontactcanproduceinflammationand
blistering
Methoxide 54.02 Hazardousincaseofskincontact(corrosive,irritant,
sensitizer,permeator),ofeyecontact(irritant,corrosive),of
ingestion,ofinhalation
2propanol 60.1 .786 Hazardousincaseofskincontact(corrosive,irritant,
sensitizer,permeator),ofeyecontact(irritant,corrosive),of
ingestion,ofinhalation
phenolphth
alein
318.32 1.28 Veryhazardousincaseofskincontact(corrosive,irritant),
ofeyecontact(irritant,corrosive),ofingestion,of
inhalation.Theamountoftissuedamagedependsonlength
ofcontact.Eyecontactcanresultincornealdamageor
blindness.Skincontactcanproduceinflammationand
blistering
Heptane 100.21 .684 Hazardousincaseofskincontact(irritant),ofeyecontact
(irritant),ofingestion,ofinhalation.Slightlyhazardousin
caseofskincontact(permeator).Severeoverexposure
canresultindeath.
Hexane 86.18 .655 Hazardousincaseofskincontact(corrosive,irritant,
sensitizer,permeator),ofeyecontact(irritant,corrosive),of
ingestion,ofinhalation
Sodium
Sulfate
142.04 2.66 Hazardousincaseofskincontact(corrosive,irritant,
sensitizer,permeator),ofeyecontact(irritant,corrosive),of
ingestion,ofinhalation
H
2
O 18.01 1.00 none

MaterialsandMethods
4

Measureout250mLofunusedvegetableoilintoaflaskandheatupto55Cwhilestirring.Do
notheatabove60C.Measure50mLofmethanolandadd1.41gramsofKOH.Swirluntildissolved.
Whentheoilreaches55Caddmethoxidetotheoil.Maintainthe55Ctemperatureforanhour.
Measure40mLof2propanolintoaflaskandadd4mLofusedoil.Warmonhotplateandadd
phenolphthalein.SlowlyaddKOHfrompipetuntilsolutionbecomespink.Recordfinalvolumeand
divideby4.Afteranhour,removefromthehotplateandpourintoacleanbottle.Allowbiodieselto
separateforaday.Pourintoaseparatecontainerandaddwatertoclean.Dothisuntilwaterisclear.
Totestqualityofbiodiesel,put150mLofbiodieselintoclearbottleandadd150mLwaterand
shakevigorously.TheoilandwatershouldseparateAnotherwaytotestistodissolve25mLofthe
biodieselinto225mLofmethanol.Thebiodieselshoulddissolvecompletely.
Tousegaschromatography,measure1mLofwaterintoadrytesttube.Add2mLheptaneor
hexanetothewater.Add2dropsofbiodieseltothemix.Shakevigorouslyandallowittorestfora
coupleminutes.Pipetthetoplayerintoacleantesttube.Addalittlesodiumsulfatetoittoabsorbthe
residualwater.Take2dropsofsolutionandplaceintoacleantesttubewith1mLofheptaneor
hexane.Recordthedata.

Discussion

Vegetableoilismainlyconsistedoftriglycerides.Athighertemperatures,thesetriglyceridescan
bereactedwithanalcoholtoformglycerolandanester.Inthisexperiment,thealcoholusedwas
methanolandthatresultedinamethylesterbeingformed.KOHwasaddedtothereactionasacatalyst
tohelpthereactionproceed.AddingKOHtomethanolproducesmethoxide,whichisaverystrong
base.TheKOHdeprotonatesthealcoholandproducesmethoxide.Intheexperiment,thisreactionwas
coveredwithParafilmtopreventabsorptionofwaterbecausewatercausesbasehydrolysis,which
degradesthereactant.Methoxideisastrongbasethatcandonateelectrons.ThismakesthemaLewis
basealso.Bydefinition,anucleophileissomethingthatcandonateanelectronpairtoformachemical
bond.Thisnucleophileattacksthethreecarbonylatomsonthetriglycerideandproducesan
intermediate.Thisintermediateishighlyunstableandbreaksintoglycerolandanester.Thisreactionis
calledtransesterification.Transesterificationisexchangingtheorganicgroupofanesterwiththeorganic
groupofanalcohol.Belowisthegeneralprocessforproducingbiodiesel.

Thedensityofthemethylestercreatedislowerthanthedensityoftheglycerolsoitfloatsupto
thetop.Thebiodieselisthencollectedfortesting.Inthewashtest,thebiodieselwasmixedwithwater
andvigorouslymixedtogether.Thebiodieselseparatedfromthewatercleanly.Thisindicatesthatthere
wasnoexcesssoapformationfromtoomuchbaseandthatthereactionwascomplete.Thesecondtest
wasamethanoltest.Thebiodieseldissolvedinsidethemethanolcompletely.Thismeansthatthe
reactionwascomplete.

References

1.FangruiMaa,MilfordAHannaBiodieselproduction:areview1999.164169.
2.YusufChisti.Biodieselfrommicroalgae2004.33193328
3.Sheehan,J.Camobreco,V.Duffield,J.Graboski,M.Shapouri,H.Lifecycleinventoryof
biodieselandpetroleumdieselforuseinanurbanbus.Finalreport.2004.201208.
4.AnIntroductiontoChemicalSystemsintheLaboratory.Halies,HaydenMcNeilPlymouth,
Michigan2014..