catalytic conversion of carbohydrates to hydrocarbons

7/31/2019 Catalytic Conversion of Carbohydrates to Hydrocarbons

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Catalytic Conversion of Carbohydrates to HydrocarbonsDOE Biomass R&D TAC Meeting

May 19, 2011

Paul Blommel, PhD

Director of Process Chemistry, Virent Energy Systems, Inc.


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BioFuel Pathways from Biomass

Biomass

Fermentation

Fermentation

AqueousPhase

Reforming

Refining

Fischer-Tropsch

Catalysis

Gasification

Pyrolysis

Hydrolysis

Syngas

Bio-oils

Sugars

DieselJet Fuel

Ethanol

MethanolEthanol

Liquid Fuels

EthanolButanolHydrocarbons

Gasoline,Jet, Diesel,Chemicals,Alcohols,

Hydrogen

CH1.4O0.6

CH1.6O0.4

CH2O

CO + H2

CH2

CH2

CH3O0.5

CH3O0.5

CH3O0.5

CH2

CH2

CH3O

0.5

Conversion ofCarbohydrates

toHydrocarbons


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O

OHOH

HO

HOCH2OH

H2OH2

CO2

n-Paraf f ins

iso-Paraffins

Aromatics

+ H2O

3.58 C6H12O6 C14H30 + 7.5 CO2 + 6.5 H2O

Overall Theoretical Stoichiometrywith in situhydrogen generation

Hydrocarbon contains 65 % of Sugar CarbonHydrocarbon contains 94% of LHV of Sugar

Generation of Hydrocarbons from Carbohydrateswith In-situHydrogen Generation

Slide 3

Potential

CarbonYield

Potential

EnergyRecovery*

Ethanol

Fermentation67% 96%

Catalytic

Conversion in

situ hydrogen

65% 94%

Catalytic

Conversion ex

situ hydrogen

100% 144%(90% including H2)

*Potential LHV of liquid fuel product/LHV ofcarbohydrate feed


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Catalytic Carbohydrate ConversionTechnology

Feedstock Flexible Conventional Sugars

Non-Food Sugars

Drop-in Products

Liquid Fuels and Chemicals

Tunable Platform

Infrastructure Compatible

Fast and Robust Inorganic Catalysts

Moderate Conditions

Low Residence Times

Energy Efficient Exothermic

Low Energy Separation

Slide 4

A catalytic route to renewable hydrocarbon fuels and chemicals.

Virent Demonstration Plant


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Aromatics and Paraffins

BioForming Platforms

APR

Modified

ZSM-5

Condensation Hydrotreating

Biomass

SugarCane

Corn

Starch

Kerosene

Jet Fuel

Diesel

Slide 5

Gasoline +

AromaticsReactive

Intermediates


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Generation of Reactive Intermediates


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Production of Hydrocarbons fromReactive Intermediates

Slide 7

APR FractionationCatalytic

Conversion

GasolineProduct

C5 & C6Sugars

Hydrolysates


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BioGasoline ProductPremium product with the same components as petroleum derived gasoline

BioForming BioGasoline+120,000 BTUs/Gal

Ethanol

76,000 BTUs/Gal

Unleaded Gasoline

115,000 BTUs/Gal

Unleaded Gasoline

BioForming

Green Gasoline

~ 20 liters of sugar derived gasoline

from Virents BioForming process.Slide 8


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Catalytic Processing Offers Flexibility toReplace More than Fuels

0.0E+00

2.0E+06

4.0E+06

6.0E+06

8.0E+06

1.0E+07

1.2E+07

1.4E+07

1.6E+07

1.8E+07

2.0E+07

0 5 10 15 20 25 30 35 40 45

FIDR

esponse

(ArbitraryUnits)

Retention Time (Minutes)

11 % Benzene

1.2% Benzene

38 % Toluene

12 % Toluene

Optimized Product for Gasoline

Blending

Composition Shifted for

Aromatics Production

Product CompositionFlexibility

Bio-reformate can replace typical reformate which is dominantfeedstock for many chemicals, fibers, and plastics in use today.

Benzene

Toluene

Para-Xylene

Meta-Xylene

Ortho-Xylene

Slide 9
http://www.google.com/imgres?imgurl=http://www.tela.it/immagini/imballi.jpg&imgrefurl=http://www.tela.it/products.html&usg=__8Hsv5gqBuazdASPuFe7SN1SuC_o=&h=544&w=621&sz=37&hl=en&start=6&sig2=QleLu1LgNSTWWMyg7arNSw&itbs=1&tbnid=FDKjLpy1xYDvKM:&tbnh=119&tbnw=136&prev=/images?q=polyurethane+foam&hl=en&gbv=2&tbs=isch:1&ei=m7zxS76nIp3sMMOpxeoL


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Process Scale Up Gasoline/Aromatics

Carbohydrates-to-Aromatics process

Scale-up of x100 from pilot plant

10,000 gallons per year

Full Length Reactor andCommercial Scale Catalyst

Product volumes for registrationand fleet testing

Feedstock handling and purification

system flexibility Operations started in November 2009

Overall success: On time, underbudget, high quality product

Slide 10
http://vnet/Pictures/Eagle/Eagle%20040.JPG


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Paraffins and Naphthenes

BioForming Platform - RPN

APR

Gasoline

Condensation Hydrotreating

Biomass

SugarCane

Corn

Starch

Gasoline +

Aromatics

Kerosene

Jet Fuel

Diesel

Slide 11

Modified

ZSM-5

ReactiveIntermediates


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Virent RPN Characteristics

Boiling Point

Polarity

Commercial Jet A-1

Virent Jet

Slide 12

Max Jet Max Diesel

Gasoline 20% 20%

Jet 50% 0%

Diesel 10% 60%

Process Oil 20% 20%

Flexible product slate

Product is uniquely advantaged

due to both component classes

and ability to meet broad boiling

point specifications

Jet certification challenging and

requires large volumes


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Feedstock flexibility for catalytic conversion

Biomass

Cellulose(35-50%)

Hemicellulose(15-35%)

Lignin(15-35%)

Others: 5-15%(Ash, Extractives)

Pentose(Xylose, Arabinose)

Hexose(Glucose, Mannose, Galactose)

Monosaccharides

Oligosaccharides

Soluble Cyclics &Phenolics

Ash & SolubleInorganics

Lignin

Sugar Degradation(Furfurals, HMF, Organic

Acids)

MicrobialConversion

CatalyticRoutes

vs.

Slide 13


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NABC Overview

Slide 14

Consortium LeadsNational Renewable Energy Laboratory

Pacific Northwest National Laboratory

Consortium PartnersAlbemarle Corporation

Amyris Biotechnologies

Argonne National Laboratory

BP Products North America Inc.

Catchlight Energy, LLC

Colorado School of Mines

Iowa State University

Los Alamos National Laboratory

Pall Corporation

RTI International

Tesoro Companies Inc.

University of California, Davis

UOP, LLCVirent Energy Systems

Washington State University

Virent leads the Catalytic Conversion of Lignocellulosic Sugars (CLS) strategy. The underlined parties above are

currently collaborating within the CLS strategy.


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Virent Deconstruction Partners

Slide 15

Dilute acid pretreatment and

enzyme hydrolysis

Wet oxidation and enzymehydrolysis

Strong acid pretreatment

Virent catalytic deconstruction

Enzyme

Hydrolysis

Dilute Acid

Deconstruction

Enzyme

Hydrolysis

Wet Oxidation

Deconstruction

Catalytic

Deconstruction

Concentrated

HCl

Deconstruction

Polyoxygenates

Furans

Carboxylic Acids

Separator


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Catalytic Lignin Conversion

Slide 16


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catalytic conversion of carbohydrates to hydrocarbons

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