Alternative paths to alcohols and hydrocarbons from biomass

• US 8,519,206 B2
• Filed: 06/20/2012
• Issued: 08/27/2013
• Est. Priority Date: 12/02/2008
• Status: Expired due to Fees

• Current Assignee: Ee-Terrabon Biofuels LLC
• Original Assignee: Ee-Terrabon Biofuels LLC, Texas A&M University System
• Inventors: Holtzapple, Mark T., Granda, Cesar B., Taco, Sebastian, Ross, Michael Kyle, Luce, Gary, Spencer, John A., Spencer, Rae L.
• Primary Examiner(s): Davis, Brian J
• Application Number:
  US13/527,991
• Publication Number:
  US 20120258508A1
• Time in Patent Office: 433 Days
• Field of Search: 585/240
• US Class Current: 585/240
• CPC Class Codes: C07C 1/24 by elimination of water
• CPC Class Codes: C07C 2/02 by addition between unsaturated hydrocarbons
• CPC Class Codes: C07C 29/149 with hydrogen or hydrogen-containing gases
• CPC Class Codes: C07C 31/08 Ethanol
• CPC Class Codes: C07C 67/04 by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
• CPC Class Codes: C07C 69/14 of monohydroxylic compounds
• CPC Class Codes: C10G 2300/1011 Biomass
• CPC Class Codes: C10G 2300/4081 Recycling aspects
• CPC Class Codes: C10G 2300/42 Hydrogen of special source or of special composition
• CPC Class Codes: C10G 2400/20 C2-C4 olefins
• CPC Class Codes: C10G 2400/22 Higher olefins
• CPC Class Codes: C10G 3/00 Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids production from non-melting solid oxygen-containing carbonaceous materials C10G1/00
• CPC Class Codes: C10G 50/00 Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation
• CPC Class Codes: C12P 7/40 containing a carboxyl group including Peroxycarboxylic acids
• CPC Class Codes: Y02P 30/20 using bio-feedstock

Abstract

A method of producing hydrocarbons from biomass that includes converting at least a portion of the biomass into a first product having at least one of a carboxylic acid, a ketone, an ammonium carboxylate salt, and combinations thereof; converting at least a portion of the first product into an alcohol; reacting at least some of the alcohol in an oligomerization reactor as part of a process that produces an oligomerization product.

Claims

1. A method of producing hydrocarbons from biomass, the method comprising:

converting at least a portion of the biomass into a first product comprising at least one of a carboxylic acid, a ketone, an ammonium carboxylate salt, and combinations thereof;

converting at least a portion of the first product into an alcohol;

reacting at least some of the alcohol in an oligomerization reactor as part of a process that produces an oligomerization product; and

separating hydrocarbons from the oligomerization product.

2. The method of claim 1, wherein converting at least a portion of the first product into an alcohol comprises reacting the carboxylic acid to form an ester and hydrogenolyzing the ester to make an alcohol.

3. The method of claim 1, wherein the first product comprises ketones, and wherein converting at least a portion of the first product into an alcohol further comprises hydrogenating ketones to make an alcohol.

4. The method of claim 1, wherein the first product comprises ammonium carboxylate salts, and wherein converting at least a portion of the first product into an alcohol further comprises reacting ammonium carboxylate salts to form an ester and hydrogenolyzing the ester to make an alcohol.

5. The method of claim 1, wherein the first product comprises carboxylic acids, and wherein converting at least a portion of the first product further comprises reacting carboxylic acids with an olefin to produce an ester;

and hydrogenolyzing the ester to produce the alcohol.

6. The method of claim 1, wherein converting at least a portion of the first product is carried out in the oligomerization reactor.

7. The method of claim 1, the method further comprising:

separating a recycle stream from the oligomerization product;

processing the recycle stream in a reformer to produce hydrogen; and

using a least a portion of the produced hydrogen for the conversion reaction of the biomass to the first product.

8. A method of producing hydrocarbons from biomass, the method comprising:

converting at least a portion of the biomass into a first product comprising one of a carboxylic acid, a ketone, an ammonium carboxylate salt, and combinations thereof;

converting at least a portion of the first product into an alcohol;

reacting at least some of the alcohol in an oligomerization reactor under suitable reaction conditions to produce a second product comprising hydrocarbons; and

separating hydrocarbons from the second product.

9. The method of claim 8, wherein converting at least a portion of the first product into an alcohol comprises:

reacting carboxylic acid with an olefin to produce an ester; and

hydrogenolyzing the ester to produce the alcohol.

10. The method of claim 9, wherein converting at least a portion of the first product is carried out in the oligomerization reactor.

11. The method of claim 10, wherein reactions in the oligomerization reactor are carried out with at least one catalyst.

12. The method of claim 8, the method further comprising:

separating a recycle stream from the second product;

processing the recycle stream in a reformer to produce hydrogen; and

using a least a portion of the produced hydrogen for the conversion reaction of the biomass to the first product.

13. The method of claim 12, the method further comprising:

separating olefins from the recycle stream prior to processing the recycle stream in a reformer to produce hydrogen; and

providing the olefins to the oligomerization reactor for the reaction that produces the second product.

14. The method of claim 8, the method further comprising:

separating a recycle stream from the second product;

separating olefins from the recycle stream; and

providing the olefins to the oligomerization reactor for the process that produces the second product.

15. A method of producing hydrocarbons from biomass, the method comprising:

converting biomass into a product stream comprising at least one of a carboxylic acid component, a carboxylate salt component, and combinations thereof;

reacting the product stream to produce an alcohol product; and

reacting at least some of the alcohol product in an oligomerization reactor as part of a process that produces an hydrocarbon oligomerization product.

16. The method of claim 15, wherein reacting the product stream is carried out in the oligomerization reactor.

17. The method of claim 15, the method further comprising:

separating a recycle stream from the hydrocarbon oligomerization product;

processing the recycle stream in a reformer to produce hydrogen; and

using a least a portion of the produced hydrogen for the conversion reaction of the biomass to the product stream.

18. The method of claim 16, the method further comprising:

separating olefins from the recycle stream prior to processing the recycle stream in a reformer to produce hydrogen; and

providing the olefins to the oligomerization reactor for the reaction that produces the oligomerization product.

19. The method of claim 15, the method further comprising:

separating a recycle stream from the hydrocarbon oligomerization product;

separating olefins from the recycle stream; and

providing the olefins to the oligomerization reactor for the process that produces the hydrocarbon oligomerization product.