Alternative paths to alcohols and hydrocarbons from biomass

• US 8,410,321 B2
• Filed: 06/19/2012
• Issued: 04/02/2013
• Est. Priority Date: 12/02/2008
• Status: Expired due to Fees

• Current Assignee: Ee-Terrabon Biofuels LLC
• Original Assignee: Ee-Terrabon Biofuels LLC
• Inventors: Holtzapple, Mark T., Granda, Cesar B., Ross, Michael Kyle, Luce, Gary, Spencer, John A., Spencer, Rae L., Taco, Sebastian
• Primary Examiner(s): Davis, Brian J
• Application Number:
  US13/526,670
• Publication Number:
  US 20120264184A1
• Time in Patent Office: 287 Days
• Field of Search: 568/884
• US Class Current: 568/885
• 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 alcohols, hydrocarbons, or both from biomass, the method including converting biomass into a carboxylic acid; reacting the carboxylic acid with an olefin to produce an ester; and hydrogenolyzing the ester to produce alcohol. The steps of reacting the carboxylic acid with an olefin to produce an ester, and hydrogenolyzing the ester to produce an alcohol, may both be carried out in the same reactor.

Claims

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

converting biomass into a carboxylic acid;

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

hydrogenolyzing the ester to produce alcohol.

2. The method of claim 1, wherein reacting the carboxylic acid with an olefin to produce an ester and hydrogenolyzing the ester to produce an alcohol are carried out in the same reactor.

3. The method of claim 2, wherein reacting the carboxylic acid with an olefin to produce an ester and hydrogenolyzing the ester to produce an alcohol are carried out with one catalyst.

4. The method of claim 1, further comprising:

dehydrating at least a portion of the alcohol to produce an olefin feed, at least a portion of the olefin feed providing the olefin that reacts with the carboxylic acid to produce the ester.

5. The method of claim 4, wherein reacting the carboxylic acid with an olefin to produce an ester and hydrogenolyzing the ester to produce an alcohol are carried out in the same reactor.

6. The method of claim 5, wherein reacting the carboxylic acid with an olefin to produce an ester and hydrogenolyzing the ester to produce an alcohol are carried out with one catalyst.

7. The method of claim 1, further comprising:

reacting at least a portion of the alcohol at suitable conditions to produce hydrocarbons.

8. The method of claim 1, wherein converting the biomass into a carboxylic acid further comprises:

fermenting the biomass to yield a liquid fermentation broth comprising water and carboxylate salts;

dewatering the liquid fermentation broth to separate the water from the carboxylate salts; and

converting the carboxylate salts into carboxylic acids.

9. The method of claim 1, furthering comprising:

converting the alcohol into a hydrocarbon.

10. The method of claim 9, wherein reacting the carboxylic acid with an olefin to produce an ester and hydrogenolyzing the ester to produce an alcohol are carried out in the same reactor.

11. The method of claim 10, wherein reacting the carboxylic acid with an olefin to produce an ester and hydrogenolyzing the ester to produce an alcohol are carried out with one catalyst.

12. The method of claim 9, wherein converting the alcohol into a hydrocarbon comprises an oligomerization process.

13. The method of claim 12, wherein the converting the alcohol into a hydrocarbon comprises:

dehydrating at least a portion of the alcohol to produce an olefin feed; and

oligomerizing at least a portion of the olefin feed to produce the hydrocarbon.