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gevogevoAdvancing the New Era of Renewables
HydrocarbonFuelsfromPlantBiomassHydrocarbonFuelsfromPlantBiomass
DavidA.Glassner,VicePresident,DavidA.Glassner,VicePresident,TechnologyTechnology
1
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gevogevo
2009Gevo,Inc. 2
gevogevoGevoisaVentureFundedCompany gevogevo
BasedinDenver,Colorado
VenturefundedbyKhoslaVentures,VirginGreenFund,
Burrill&CompanyandMalaysianLifeScienceFund
~50people
Morethan100patents&applicationsincludingexclusive
licensesfromUCLAandCargill
Pilotplant,laboratory&officespaceinDenver,Coloradototaling30,000squarefeet
Exclusivedevelopment&commercializationagreementswithICMincludingretrofit&useof1milliongallonperyearpilotplantinSt.Joseph,MO
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gevogevo
2009Gevo,Inc. 3
gevogevoKeyMessages gevogevo
Hydrocarbonfuelsthatsolverefinerschallengesandprovideenvironmentalbenefitscanbemadefromplantbiomassviathefermentationintermediateisobutanol
Highyieldisobutanolfermentationdeveloped
Chemistrytoconvertisobutanoltoavarietyofhydrocarbonfuelsmolecules
issimpleandwellknown
Processtechnologyforhydrocarbonsislowenergyinputandreducesgreenhousegasemissionsby85%
Cashoperatingcostforhydrocarbonfueliscompetitivewith$65
perbarrelcrudeoil(withoutincentives)
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gevogevogevogevo
2009Gevo,Inc. 4
IntroductiontoHydrocarbonsviaIntroductiontoHydrocarbonsviaIsobutanolFromCelluloseIsobutanolFromCellulose
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gevogevo
2009Gevo,Inc. 5
gevogevoHydrocarbonsCanbeManufacturedfromAnyCarbohydrateviaIsobutanolFermentation!
Isobutanol+$560Million
IntermediateBuildingBlocks
+$30Billion
NicheFuelBlendstocks
NicheFuelBlendstocks
ChemicalMarketChemicalMarket
Isobutanol+$40Billion
LowRVPHydrocarbons+$60Billion
FuelHydrocarbonsFuelHydrocarbons
Gasoline+$500B
JetFuel+$300B
Diesel+$500B
9FermentationProven9ProcessProvenatPilot9ReadyForDemoPlant
9FermentationProven9ProcessProvenatPilot9ReadyForDemoPlant9Cellulosicproven9Cellulosicproven
Madeandtested:9Gasoline9JetFuel9AvGas
Madeandtested:9Gasoline9JetFuel9AvGas
gevogevo
Madeandtested:9Isobutanol9Isobutylene9pXylene9Terephthalicacid9Isooctene9Alkylate9DieselBlendstock
Madeandtested:9Isobutanol9Isobutylene9pXylene9Terephthalicacid9Isooctene9Alkylate9DieselBlendstock
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gevogevo
2009Gevo,Inc. 6
gevogevoHydrocarbonsfromCelluloseProcessSchematic
Thenewportion
oftheprocessistheisobutanolfermentationandpurification
Manycellulosehydrolysisprocessesarebeingdevelopedforcommercialization
Isobutanoldehydrationtoisobutyleneisasimpleprocess
Isobutyleneoligomerizationispracticedinrefineriestodayonamixed
olefinstream
CelluloseHydrolysis
FermentationIsobutanolPurification
IsobutanolDehydration
IsobutyleneOligomerization
Sugars Isobutanolbroth
Isobutanol
IsobutyleneHydrocarbonfuels
Biomass
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2009Gevo,Inc. 7
IsobutanolFermentationIsobutanolFermentation
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2009Gevo,Inc. 8
gevogevoGevosPathwayMakesOnlyIsobutanol!glucose
2pyruvate
acetolactate
ketoisovalerate
2,3dihydroxyisovalerate
isobutyraldehyde
isobutanol
CO2
CO2
ALS
KARI
DHAD
KIVD
ADH
GLYCOLYSIS
Onemoleofglucose(MW180)yields 1molesofisobutanol(MW74X1=74)
2molesofcarbondioxide(MW44X2=88)1moleofwater(MW18X1=18)
Theoreticalisobutanolmassyieldis41.1%
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gevogevo
2009Gevo,Inc. 9
IsobutanolFermentationMeetsFeasibilityTargets!
Target
CornDryMillTarget
CellulosicBiomassTarget
Source:GevoTestingActualPlan
GasChromatographofFermentationBroth
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gevogevo
2009Gevo,Inc. 10
gevogevoGevosBiocatalystConvertsCellulosicSugars!
Isobutanolcanbeproducedfromavarietyoflignocellulosicsugars
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2009Gevo,Inc. 11
gevogevoEthanol ABE Isobutanol Comments
Volumetricproductivity(g/l/hr)
2.5 0.5 2.0
Fermentorvolumesincreasedifglycolyticfluxisnotmaintained
Massyield(Theoretical)
0.480.51
0.340.40
0.390.41
Hightiterofsugarconvertedtoethanolandisobutanolkeepsyieldhigh
Finaltiter 130g/l 28g/l 105g/l
Highconcentrationkeepsenergycostlow
Microorganism Yeast Clostridia Yeast
Yeastareproveninlowcostindustrialfermentors
Allarebatchfermentationdata
ABEdataincludeshydrogenproduction(Jones,MicrobiologicalReview,
1986)
LowCostProductionRequiresHighPerformanceFermentation!
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2009Gevo,Inc. 12
HydrocarbonFuelsfromIsobutanolHydrocarbonFuelsfromIsobutanol
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2009Gevo,Inc. 13
gevogevoAdvancingtheNewEraofRenewables
Fuels
IsobutyleneIsobutanol
H2O
BioGasolineBlendstocks
BioDieselBlendstocks/Additives
Xylenesandotheraromatics terephthalicacid
PETotherpolymers
+C8, C12, C16MixturesBioJetFuel
Isooctene
OtherMonomers
Solvents
or
ETBE
MethylMethacrylate(MMA)
ButylRubber
Additives(antioxidants,plasticsmodifiers)
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2009Gevo,Inc. 14
JetFuelBlendstockMeetsASTMSpecifications!JetFuelBlendstockMeetsASTMSpecifications!
Valueadded: Flashpointishigh Freezingpointislow
Flexibilitytoblend
Uniquecompositionispatentable
FirstSasolSyntheticJetwasC12centeredisoparaffinmixturewithsimilarproperties
Asismeetsall
ASTMspecificationsexceptvolumetricdensity(0.768kg/Lvs.0.775kg/L)
Blendingwith25%JetAorwith10%GevoaromaticsmeetsallASTMspecifications
D1655specificationmaybechangedtolowerdensity
T50T10meetsproposedsyntheticjetfuelrequirements
Meetsenergydensity(43.2MJ/kgvs.42.8MJ/kg)
GCFIDAgilent7890A,DB5column,temperatureprogramstartedat40Cheatedupat10C/minto240C
iC12 GevoJetFuel
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gevogevogevogevo
2009Gevo,Inc. 15
Density(g/L)
RVP(psi)OctaneNumber[(R+M)/2]
GevoButanes 580 54 92
GevoIsooctanes 700 2 98100
GevoOlefins 716 1.8 103
GevoAromatics 870 23 99
GevoIsobutanol 802 45 98102
GevoGasolineBlend
740 7 99
ConventionalGasoline
GevoGasoline
GasolineMeetingASTMSpecificationsDemonstrated!GasolineMeetingASTMSpecificationsDemonstrated!
Gasolineiscomposedofthreemajorcomponents:
HighRVPmaterialtoprovideignitablevaportoengine
pentanes,butanes,lightolefinsfromsomerefineries
LowRVP,highoctane,highenergyaliphaticmaterialforenergycontentandperformance
C6C10isoparaffins,primarilyisooctenes/isooctanes
LowRVP,highoctane,highenergyaromaticmaterialforenergy
contentandperformance
BTX(benzene,toluene,xylenes)fromreformer
Higherlevelsofaromaticsareinpremiumblends
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2009Gevo,Inc. 16
HighCetaneDieselFuelDemonstrated!HighCetaneDieselFuelDemonstrated!
Challengeistoconvertbranchedolefintounbranchedoligomerswithhighcetane:
Evenunbranchedolefinsusuallyoligomerizetoisoparaffins
Linearparaffinsareproducedcommerciallywithexpensiveoligomerizationofethylene
Hightemperaturesfavorunbranchedmaterialbutcrackingoccurs
Keystrategyforgeneratinglinearparaffins:
Useshapeselectivecatalyststopreventbranchedmaterialfromforming
Inactivatesurfaceofcatalystsothatonlyshapeselectiveportionreacts
Runreactionathighesttemperaturepossiblewithoutcracking
Results: Conditions collidinetreatedZSM5zeoliteat220Cand1300psi
Monomethylparaffinfractionproducedin>20%yield(20gproduct/90gisobutylene)
MonomethylparaffinsmeetASTMspecsforNo.1Dieselincluding
cetanenumber>68
GevoDieselhascetane#>50
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2009Gevo,Inc. 17
AromaticsCompoundsDemonstrated!AromaticsCompoundsDemonstrated!
pXyleneandTerepthalicAcidfromIsooctene:
OptimizedinlabtoprepareforproductionfromGevoisobutanol
pxylenefromisooctene:>95%selectivity,highestsinglepassconversioninliterature
terepthalicacidfrompxylene:highyieldandcleanproduct
min5 10 15 20 25
Norm.
0
1000
2000
3000
4000
5000
6000
FID1 A, Front Signal (S:\P-XYLENE.D) FID1 A, Front Signal
(S:\RUN 66 CUT BOTTOM.D)
BTEX(Benzene,Toluene,Ethylbenzene,Xylenes):
Producedfromisobutyleneusingtypicalrefineryreformingconditions
Primaryproductisbenzeneandtoluene,byproductsarehydrogenandcrackedHCs
HeavyAromatics(tButylBenzenes)forJetFuel:
Alkylationofbenzeneandtoluenewithisobutylene
Alkylatedbenzeneshavehighflashpoint,burncleanerthannapthalenes
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2009Gevo,Inc. 18
TechnologySummaryTechnologySummary
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2009Gevo,Inc. 19
gevogevoHydrocarbonsConservetheBiomassEnergy!Ethanol Isobutanol
Isooctene
Energycontentoffuel(BTUs/gallon) 76,000 95,000 112,000
Fueldensity(g/ml) 0.7894 0.8106 0.7331
Energycontentoffuel(BTUs/pound) 11,600 14,100
17,500
Massfractionfuelyield(poundsfuelperpoundsugar) 0.48 0.39
0.30
Energyproduced(BTUsfuelperpoundsugarconverted)
5,500 5,500 5,400
gevogevo
185%isooctenesand15%C12s
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gevogevo
2009Gevo,Inc. 20
gevogevoIsobutanolRecoveryEnergyisVeryLow!Ethanol Isobutanol
BTUsenergypergallonfuelrecovered14,000 15,000
BTUsenergyperBTUfuelrecovered0.18 0.16
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gevogevo
2009Gevo,Inc. 21
gevogevoHydrocarbonsfromCelluloseReduceGreenhouseGasEmissionsby85%ComparedtoGasoline
Isooctene Gasoline
Greenhousegasemissions(carbondioxideequivalentgramspermillionBTUoffuel)BasedonWanget.Al.,2007
15,0001,2 98,0001
1 GreenhousegasemissionsfromWanget.al.,20072
Cellulosicconversionprocessusingswitchgrass,diluteacid
prehydrolysisandcellulaseenzymehydrolysis.
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2009Gevo,Inc. 22
gevogevoHydrocarbonsareAbouttheSameCostperBTUasEthanol!Ethanol
Isobutanol Isooctene
Rich1
Cashoperatingcost($/gallon) 1.18 1.44 1.86
Gallonsfuelfor1millionBTUsfuel 13.2 10.5 9.4
Cashoperatingcost($/millionBTUsfuel)
15.53 15.16 16.62
At$65/barrelcrudewholesalegasolineisabout$1.80pergallon
Cashoperatingcostfor$50/tonbiomassor$3/bushelcorn
Isooctenerichfractionisapremiumgasolineblendstockwith1.8
RVPand96octane(1540centspergallonpremiumtowholesalegasoline)
HelpsrefinersmeetlowvaporpressuregasolineregulationstoreduceozoneandVOCs
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2009Gevo,Inc. 23
PathwaytoCommercializationPathwaytoCommercialization
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2009Gevo,Inc. 24
gevogevo
iBuOHProcessUnit(~$30Mcapitalcostto
retrofit100MGPYEthanol)
CommercializationStrategyAccesscapacityviaretrofitsofexistingethanol(tolling)
EntermarketwithhighvaluefuelproductsUseexistingpetrochemicalchannelsandinfrastructureAddtechnologyandproductioncapabilityincrementally
Readilyscalabletechnology
CommercializationStrategyAccesscapacityviaretrofitsofexistingethanol(tolling)
EntermarketwithhighvaluefuelproductsUseexistingpetrochemicalchannelsandinfrastructureAddtechnologyandproductioncapabilityincrementally
Readilyscalabletechnology
CapitalLightApproach:RepurposeEthanolPlants
BiocatalystChange
AnimalFeed(~4kgforeachgallonproduced)
gevogevo
Step1
Step2HydrocarbonUnit(~$18Mcapitalcost
for100MGPYEthanol)BiomassConvertingUnitStep3
DieselJet
Gasoline
Isobutanol
HydrocarbonsChemicals
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2009Gevo,Inc. 25
gevogevoKeyMessages gevogevo
Hydrocarbonfuelsthatsolverefinerschallengesandprovideenvironmentalbenefitscanbemadefromplantbiomassviathefermentationintermediateisobutanol
Highyieldisobutanol fermentationdeveloped
Chemistrytoconvertisobutanol
toavarietyofhydrocarbonfuelsmolecules
issimpleandwellknown
Processtechnologyforhydrocarbonsislowenergyinputandreducesgreenhousegasemissionsby85%
Cashoperatingcostforhydrocarbonfueliscompetitivewith$65
perbarrelcrudeoil(withoutincentives)
