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Advancing the New Era of Renewables
HydrocarbonFuelsfromPlantBiomass HydrocarbonFuelsfromPlantBiomass
DavidA.Glassner,VicePresident, DavidA.Glassner,VicePresident,
Technology Technology
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GevoisaVentureFundedCompany
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BasedinDenver,Colorado
VenturefundedbyKhoslaVentures,VirginGreenFund,
Burrill&CompanyandMalaysianLifeScienceFund
~50people
Morethan100patents&applicationsincludingexclusive
licensesfromUCLAandCargill
Pilotplant,laboratory&officespaceinDenver,Colorado
totaling30,000squarefeet
Exclusivedevelopment&commercializationagreements
withICMincludingretrofit&useof1milliongallonperyear
pilotplantinSt.Joseph,MO
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KeyMessages
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Hydrocarbonfuelsthatsolverefinerschallengesand
provideenvironmentalbenefitscanbemadefromplant
biomassviathefermentationintermediateisobutanol
Highyieldisobutanolfermentationdeveloped
Chemistrytoconvertisobutanoltoavarietyofhydrocarbonfuelsmolecules
issimpleandwellknown
Processtechnologyforhydrocarbonsislowenergyinputandreduces
greenhousegasemissionsby85%
Cashoperatingcostforhydrocarbonfueliscompetitivewith$65 perbarrel
crudeoil(withoutincentives)
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IntroductiontoHydrocarbonsvia
IntroductiontoHydrocarbonsvia
IsobutanolFromCellulose
IsobutanolFromCellulose
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HydrocarbonsCanbeManufacturedfromAnyCarbohydrate
viaIsobutanolFermentation!
Isobutanol
+$560Million
IntermediateBuilding
Blocks
+$30Billion
NicheFuelBlend
stocks
NicheFuelBlend
stocks
ChemicalMarket
ChemicalMarket
Isobutanol
+$40Billion
LowRVPHydrocarbons
+$60Billion
FuelHydrocarbons
FuelHydrocarbons
Gasoline
+$500B
JetFuel
+$300B
Diesel
+$500B
FermentationProven
ProcessProvenatPilot
ReadyForDemoPlant
FermentationProven
ProcessProvenatPilot
ReadyForDemoPlant
Cellulosicproven
Cellulosicproven
Madeandtested:
Gasoline
JetFuel
AvGas
Madeandtested:
Gasoline
JetFuel
AvGas
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Madeandtested:
Isobutanol
Isobutylene
pXylene
Terephthalicacid
Isooctene
Alkylate
DieselBlendstock
Madeandtested:
Isobutanol
Isobutylene
pXylene
Terephthalicacid
Isooctene
Alkylate
DieselBlendstock
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HydrocarbonsfromCelluloseProcessSchematic
Thenewportion oftheprocessistheisobutanolfermentationand
purification
Manycellulosehydrolysisprocessesarebeingdevelopedfor
commercialization
Isobutanoldehydrationtoisobutyleneisasimpleprocess
Isobutyleneoligomerizationispracticedinrefineriestodayonamixed
olefinstream
Cellulose
Hydrolysis
Fermentation
Isobutanol
Purification
Isobutanol
Dehydration
Isobutylene
Oligomerization
Sugars
Isobutanol
broth
Isobutanol
Isobutylene
Hydrocarbonfuels
Biomass
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IsobutanolFermentation
IsobutanolFermentation
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GevosPathwayMakesOnlyIsobutanol!
glucose
2pyruvate
acetolactate
ketoisovalerate
2,3dihydroxyisovalerate
isobutyraldehyde
isobutanol
CO
2
CO
2
ALS
KARI
DHAD
KIVD
ADH
GLYCOLYSIS
Onemoleofglucose
(MW180)yields
1molesof
isobutanol(MW74X1
=74)
2molesofcarbon
dioxide(MW44X2=
88)
1moleofwater
(MW18X1=18)
Theoreticalisobutanol
massyieldis41.1%
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IsobutanolFermentationMeetsFeasibilityTargets!
Target
CornDryMillTarget
CellulosicBiomassTarget
Source:GevoTesting
Actual
Plan
GasChromatographofFermentationBroth
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GevosBiocatalystConvertsCellulosicSugars!
Isobutanolcanbeproducedfromavarietyoflignocellulosicsugars
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Ethanol ABE Isobutanol Comments
Volumetric
productivity
(g/l/hr)
2.5 0.5 2.0 Fermentorvolumesincreasedif
glycolyticfluxisnotmaintained
Massyield
(Theoretical)
0.48
0.51
0.34
0.40
0.39
0.41
Hightiterofsugarconvertedto
ethanolandisobutanolkeepsyield
high
Finaltiter 130g/l 28g/l 105g/l Highconcentrationkeepsenergy
costlow
Microorganism Yeast Clostridia Yeast Yeastareproveninlowcost
industrialfermentors
Allarebatchfermentationdata
ABEdataincludeshydrogenproduction(Jones,MicrobiologicalReview,
1986)
LowCostProductionRequires
HighPerformanceFermentation!
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HydrocarbonFuelsfromIsobutanol
HydrocarbonFuelsfromIsobutanol
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AdvancingtheNewEraofRenewables
Fuels
Isobutylene
Isobutanol
H
2
O
BioGasolineBlendstocks
BioDieselBlendstocks/Additives
Xylenesandother
aromatics
terephthalicacid
PET
otherpolymers
+C
8
, C
12
, C
16
Mixtures BioJetFuel
Isooctene
OtherMonomers
Solvents
or
ETBE
MethylMethacrylate(MMA)
ButylRubber
Additives(antioxidants,plasticsmodifiers)
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JetFuelBlendstockMeetsASTMSpecifications!
JetFuelBlendstockMeetsASTMSpecifications!
Valueadded:
Flashpointishigh
Freezingpointislow
Flexibilitytoblend
Uniquecompositionispatentable
FirstSasolSyntheticJetwasC12
centeredisoparaffinmixturewith
similarproperties
Asismeetsall ASTM
specificationsexceptvolumetric
density(0.768kg/Lvs.0.775kg/L)
Blendingwith25%JetAorwith10%
GevoaromaticsmeetsallASTM
specifications
D1655specificationmaybechanged
tolowerdensity
T50T10meetsproposedsynthetic
jetfuelrequirements
Meetsenergydensity(43.2MJ/kg
vs.42.8MJ/kg)
GCFIDAgilent7890A,DB5column,temperatureprogramstartedat40Cheatedupat10C/minto240C
iC
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GevoJetFuel
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Density
(g/L)
RVP(psi)
Octane
Number
[(R+M)/2]
GevoButanes 580 54 92
GevoIsooctanes 700 2 98100
GevoOlefins 716 1.8 103
GevoAromatics 870 23 99
GevoIsobutanol 802 45 98102
GevoGasoline
Blend
740 7 99
Conventional
Gasoline
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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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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AromaticsCompoundsDemonstrated!
AromaticsCompoundsDemonstrated!
pXyleneandTerepthalicAcidfromIsooctene:
OptimizedinlabtoprepareforproductionfromGevoisobutanol
pxylenefromisooctene:>95%selectivity,highestsinglepassconversioninliterature
terepthalicacidfrompxylene:highyieldandcleanproduct
min 5 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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TechnologySummary
TechnologySummary
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HydrocarbonsConservetheBiomassEnergy!
Ethanol Isobutanol Isooctene
Energycontentoffuel
(BTUs/gallon)
76,000 95,000 112,000
Fueldensity(g/ml)
0.7894 0.8106 0.733
1
Energycontentoffuel
(BTUs/pound)
11,600 14,100 17,500
Massfractionfuelyield
(poundsfuelperpoundsugar)
0.48 0.39 0.30
Energyproduced(BTUsfuel
perpoundsugarconverted)
5,500 5,500 5,400
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85%isooctenesand15%C12s
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IsobutanolRecoveryEnergyisVeryLow!
Ethanol Isobutanol
BTUsenergypergallonfuelrecovered
14,000 15,000
BTUsenergyperBTUfuelrecovered
0.18 0.16
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HydrocarbonsfromCelluloseReduce
GreenhouseGasEmissionsby85%ComparedtoGasoline
Isooctene Gasoline
Greenhousegasemissions(carbon
dioxideequivalentgramspermillion
BTUoffuel)BasedonWanget.Al.,
2007
15,000
1,2
98,000
1
1
GreenhousegasemissionsfromWanget.al.,2007
2
Cellulosicconversionprocessusingswitchgrass,diluteacid
prehydrolysisandcellulaseenzymehydrolysis.
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HydrocarbonsareAbouttheSameCostperBTUasEthanol!
Ethanol Isobutanol Isooctene
Rich
1
Cashoperatingcost($/gallon) 1.18 1.44 1.86
Gallonsfuelfor1millionBTUsfuel 13.2 10.5 9.4
Cashoperatingcost($/millionBTUs
fuel)
15.53 15.16 16.62
At$65/barrelcrudewholesalegasolineisabout$1.80pergallon
Cashoperatingcostfor$50/tonbiomassor$3/bushelcorn
Isooctenerichfractionisapremiumgasolineblendstockwith1.8
RVPand96octane(1540centspergallonpremiumtowholesale
gasoline)
Helpsrefinersmeetlowvaporpressuregasolineregulationsto
reduceozoneandVOCs
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PathwaytoCommercialization
PathwaytoCommercialization
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iBuOHProcessUnit
(~$30Mcapitalcostto
retrofit100MGPYEthanol)
CommercializationStrategy
Accesscapacityviaretrofitsofexistingethanol(tolling)
Entermarketwithhighvaluefuelproducts
Useexistingpetrochemicalchannelsandinfrastructure
Addtechnologyandproductioncapabilityincrementally
Readilyscalabletechnology
CommercializationStrategy
Accesscapacityviaretrofitsofexistingethanol(tolling)
Entermarketwithhighvaluefuelproducts
Useexistingpetrochemicalchannelsandinfrastructure
Addtechnologyandproductioncapabilityincrementally
Readilyscalabletechnology
CapitalLightApproach:RepurposeEthanolPlants
Biocatalyst
Change
AnimalFeed
(~4kgforeachgallonproduced)
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Step1
Step2
HydrocarbonUnit
(~$18Mcapitalcost
for100MGPYEthanol)
BiomassConvertingUnit
Step3
Diesel
Jet
Gasoline
Isobutanol
Hydrocarbons
Chemicals
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KeyMessages
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Hydrocarbonfuelsthatsolverefinerschallengesand
provideenvironmentalbenefitscanbemadefromplant
biomassviathefermentationintermediateisobutanol
Highyieldisobutanol fermentationdeveloped
Chemistrytoconvertisobutanol toavarietyofhydrocarbonfuelsmolecules
issimpleandwellknown
Processtechnologyforhydrocarbonsislowenergyinputandreduces
greenhousegasemissionsby85%
Cashoperatingcostforhydrocarbonfueliscompetitivewith$65 perbarrel
crudeoil(withoutincentives)