Title: Catalytic conversion of cellulose to liquid hydrocarbon fuels by progressive removal of oxygen to facilitate separation processes and achieve high selectivities

Abstract

Described is a method to make liquid chemicals. The method includes deconstructing cellulose to yield a product mixture comprising levulinic acid and formic acid, converting the levulinic acid to .gamma.-valerolactone, and converting the .gamma.-valerolactone to pentanoic acid. Alternatively, the .gamma.-valerolactone can be converted to a mixture of n-butenes. The pentanoic acid can be decarboxylated yield 1-butene or ketonized to yield 5-nonanone. The 5-nonanone can be hydrodeoxygenated to yield nonane, or 5-nonanone can be reduced to yield 5-nonanol. The 5-nonanol can be dehydrated to yield nonene, which can be dimerized to yield a mixture of C.sub.9 and C.sub.18 olefins, which can be hydrogenated to yield a mixture of alkanes.

Inventors:

Dumesic, James A.; Ruiz, Juan Carlos Serrano; West, Ryan M.

Issue Date:

2015-06-30

Research Org.:

Wisconsin Alumni Research Foundation, Madison, WI (United States)

Sponsoring Org.:

USDOE

OSTI Identifier:

1187952

Patent Number(s):

9067903

Application Number:

14/093,907

Assignee:

Wisconsin Alumni Research Foundation (Madison, WI)

Patent Classifications (CPCs):

B - PERFORMING OPERATIONS B01 - PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL B01J - CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY

C - CHEMISTRY C01 - INORGANIC CHEMISTRY C01B - NON-METALLIC ELEMENTS

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B - PERFORMING OPERATIONS B01 - PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL B01J - CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY

B01J23/10 - of rare earths
B01J23/6484 - {Niobium}
B01J35/0006 - {Catalysts containing parts with different compositions}
B01J35/1019 - {100-500 m2/g}

C - CHEMISTRY C01 - INORGANIC CHEMISTRY C01B - NON-METALLIC ELEMENTS

C01B2203/0233 - the reforming step being a steam reforming step
C01B2203/06 - Integration with other chemical processes
C01B2203/065 - using hydrotreating, e.g. hydrogenation, hydrodesulfurisation
C01B2203/1211 - Organic compounds or organic mixtures used in the process for making hydrogen or synthesis gas
C01B3/32 - by reaction of gaseous or liquid organic compounds with gasifying agents, e.g. water, carbon dioxide, air

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C1/213 - by splitting of esters
C07C1/24 - by elimination of water
C07C11/02 - Alkenes
C07C11/08 - with four carbon atoms
C07C2521/12 - Silica and alumina
C07C2527/054 - Sulfuric acid or other acids with the formula H2Sn03n+1
C07C2527/08 - Halides
C07C2527/11 - Hydrogen chloride
C07C2527/1206 - Hydrogen fluoride
C07C2527/173 - Phosphoric acid or other acids with the formula Hn+2PnO3n+1
C07C2531/04 - containing carboxylic acids or their salts
C07C51/00 - Preparation of carboxylic acids or their salts, halides or anhydrides
C07C51/09 - from carboxylic acid esters or lactones
C07C53/126 - Acids containing more than four carbon atoms
C07C59/185 - Saturated compounds having only one carboxyl group and containing keto groups

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS

C07D307/33 - in position 2, the oxygen atom being in its keto or unsubstituted enol form
C07D309/12 - only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers

C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10G - CRACKING HYDROCARBON OILS

C10G2300/1014 - of vegetal origin
C10G2400/20 - C2-C4 olefins
C10G3/42 - {Catalytic treatment}
C10G3/45 - {containing iron group metals or compounds thereof}
C10G3/47 - {containing platinum group metals or compounds thereof}

Y - NEW / CROSS SECTIONAL TECHNOLOGIES Y02 - TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE Y02P - CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

Y02P30/20 - Bio-feedstock

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DOE Contract Number:  

FG02-03ER15468

Resource Type:

Patent

Resource Relation:

Patent File Date: 2013 Dec 02

Country of Publication:

United States

Language:

English

Subject:

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 09 BIOMASS FUELS