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US8053615: Synthesis of liquid fuels and chemicals from oxygenated hydrocarbons

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Filing Information

Inventor(s) Randy D. Cortright · Paul G. Blommel ·
Assignee(s) Virent Energy Systems, Inc. ·
Attorney/Agent(s) Quarles & Brady LLP ·
Primary Examiner N. Bhat ·
Application Number US12044837
Filing date 03/07/2008
Issue date 11/08/2011
Prior Publication Data
Predicted expiration date 10/18/2029
Patent term adjustment 590
U.S. Classifications 585/240  · 423/437.1  · 585/324  · 568/801  · 585/242  ·
International Classifications C07C2960  · C07C400  ·
Kind CodeB2
Related U.S. Application DataCROSS REFERENCE TO RELATED APPLICATIONS
This application claims benefit of U.S. Provisional Application Nos. 60/985,475 filed on Nov. 5, 2007, 60/985,500 filed on Nov. 5, 2007, and, 60/905,703 filed on Mar. 8, 2007.
Commonly owned U.S. Nonprovisional application Ser. No. 11/961,280 filed on Dec. 20, 2007, discloses related subject matter.
Commonly owned U.S. Nonprovisional application Ser. No. 11/800,671 filed on May 7, 2007, now U.S. Pat. No. 7,767,867 discloses related subject matter.
Commonly owned PCT Application No. PCT/US06/048030 filed on Dec. 18, 2006, discloses related subject matter.
147 Claims, 20 Drawings


Abstract

Processes and reactor systems are provided for the conversion of oxygenated hydrocarbons to hydrocarbons, ketones and alcohols useful as liquid fuels, such as gasoline, jet fuel or diesel fuel, and industrial chemicals. The process involves the conversion of mono-oxygenated hydrocarbons, such as alcohols, ketones, aldehydes, furans, carboxylic acids, diols, triols, and/or other polyols, to C4+ hydrocarbons, alcohols and/or ketones, by condensation. The oxygenated hydrocarbons may originate from any source, but are preferably derived from biomass.

Independent Claims | See all claims (147)

  1. 1. A method of making a C4+ compound comprising: providing water and a water soluble oxygenated hydrocarbon comprising a C1+O1+ hydrocarbon in an aqueous liquid phase and/or a vapor phase, providing H2, catalytically reacting in the liquid and/or vapor phase the oxygenated hydrocarbon with the H2 in the presence of a deoxygenation catalyst at a deoxygenation temperature and deoxygenation pressure to produce an oxygenate comprising a C1+O1-3 hydrocarbon in a reaction stream, and catalytically reacting in the liquid and/or vapor phase the oxygenate in the presence of an acid catalyst at a condensation temperature and condensation pressure to produce the C4+ compound, wherein the C4+ compound comprises a member selected from the group consisting of C4+ alcohol, C4+ ketone, C4+ alkane, C4+ alkene, C5+ cycloalkane, C5+ cycloalkane, aryl, fused aryl, and a mixture thereof.
  2. 104. A method of making a C4+ compound comprising: providing water and a water soluble oxygenated hydrocarbon comprising a C1+O1+ hydrocarbon in an aqueous liquid phase and/or a vapor phase, catalytically reacting a portion of the water and oxygenated hydrocarbon in the liquid phase and/or vapor phase in the presence of an aqueous phase reforming catalyst at a reforming temperature and a reforming pressure to produce in situ generated H2, catalytically reacting in the liquid and/or vapor phase the oxygenated hydrocarbon with the in situ generated H2 in the presence of a deoxygenation catalyst at a deoxygenation temperature and deoxygenation pressure to produce an oxygenate comprising a C1+O1-3 hydrocarbon in a reaction stream, and catalytically reacting in the liquid and/or vapor phase the oxygenate in the presence of an acid catalyst at a condensation temperature and condensation pressure to produce the C4+ compound, wherein the C4+ compound comprises a member selected from the group consisting of C4+ alcohol, C4+ ketone, C4+ alkane, C4+ alkene, C5+ cycloalkane, C5+ cycloalkene, aryl, fused aryl, and a mixture thereof.
  3. 140. A method of making a C4+ compound comprising: providing an aqueous solution comprising water and a member selected from the group consisting of a sugar, furfural, carboxylic acid, ketone, furan, and a combination thereof; catalytically reacting in a liquid and/or vapor phase the sugar, furfural, carboxylic acid, ketone, furan, or combination thereof, with H2 in the presence of a hydrogenation catalyst at a hydrogenation temperature and hydrogenation pressure to produce an oxygenated hydrocarbon comprising a C1+O1-3 hydrocarbon, catalytically reacting a portion of the water and oxygenated hydrocarbon in the liquid phase and/or vapor phase in the presence of an aqueous phase reforming catalyst at a reforming temperature and a reforming pressure to produce in situ generated H2, catalytically reacting in the liquid and/or vapor phase the oxygenated hydrocarbon with the in situ generated H2 in the presence of a deoxygenation catalyst at a deoxygenation temperature and deoxygenation pressure to produce an oxygenate comprising a C1+O1-3 hydrocarbon, and catalytically reacting in the liquid and/or vapor phase the oxygenate in the presence of an acid catalyst at a condensation temperature and condensation pressure to produce the C4+ compound, wherein the C4+ compound comprises a member selected from the group consisting of C4+ alcohol, C4+ ketone, C4+ alkane, C4+ alkene, C5+ cycloalkane, C5+ cycloalkene, aryl, fused aryl, and a mixture thereof.
  4. 144. A method of making a C4+ compound comprising: providing an aqueous solution comprising water and a member selected from the group consisting of a polysaccharide, disaccharide, monosaccharide, polyhydric alcohol, sugar, sugar alcohol, and a combination thereof; catalytically reacting in a liquid and/or vapor phase the sugar, sugar alcohol, polysaccharide, disaccharide, monosaccharide, polyhydric alcohol, or combination, with H2 in the presence of a hydrogenolysis catalyst at a hydrogenolysis temperature and hydrogenolysis pressure to produce an oxygenated hydrocarbon comprising a C1+O1+ hydrocarbon, catalytically reacting a portion of the water and oxygenated hydrocarbon in the liquid phase and/or vapor phase in the presence of an aqueous phase reforming catalyst at a reforming temperature and a reforming pressure to produce in situ generated H2, catalytically reacting in the liquid and/or vapor phase the oxygenated hydrocarbon with the in situ generated H2 in the presence of a deoxygenation catalyst at a deoxygenation temperature and deoxygenation pressure to produce an oxygenate comprising a C1+O1-3 hydrocarbon, and catalytically reacting in the liquid and/or vapor phase the oxygenate in the presence of an acid catalyst at a condensation temperature and condensation pressure to produce the C4+ compound, wherein the C4+ compound comprises a member selected from the group consisting of C4+ alcohol, C4+ ketone, C4+ alkane, C4+ alkene, C5+ cycloalkane, C5+ cycloalkene, aryl, fused aryl, and a mixture thereof.

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US8283506 UOP LLC Peter Kokayeff et al. Oct 2012
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