Production of alcohol esters and in situ product removal during alcohol fermentation

• US 9,040,263 B2
• Filed: 07/28/2011
• Issued: 05/26/2015
• Est. Priority Date: 07/28/2010
• Status: Active Grant

• Current Assignee: Gevo Incorporated
• Original Assignee: Butamax(TM) Advanced Biofuels LLC (BP PLC)
• Inventors: Anton, Douglas Robert, Bazzana, Stephane Francois, Burlew, Keith H., Cirakovic, Jelena, Dicosimo, Robert, Diner, Bruce A., Grady, Michael Charles, Roesch, Brian Michael, Woerner, Francis J.
• Primary Examiner(s): NOAKES, SUZANNE MARIE
• Application Number:
  US13/193,147
• Publication Number:
  US 20120208246A1
• Time in Patent Office: 1,398 Days
• Field of Search: None
• US Class Current: 435/134
• CPC Class Codes: A23K 10/12 by fermentation of natural products, e.g. of vegetable material, animal waste material or biomass
• CPC Class Codes: A23K 10/38 from distillers' or brewers' waste
• CPC Class Codes: C12P 2203/00 Fermentation products obtained from optionally pretreated or hydrolyzed cellulosic or lignocellulosic material as the carbon source ethanol C12P7/10
• CPC Class Codes: C12P 7/16 Butanols
• CPC Class Codes: C12P 7/62 Carboxylic acid esters
• CPC Class Codes: C12P 7/649 Biodiesel, i.e. fatty acid alkyl esters
• CPC Class Codes: Y02E 50/10 Biofuels, e.g. bio-diesel
• CPC Class Codes: Y02P 60/87 Re-use of by-products of food processing for fodder production

Abstract

An alcohol fermentation process and composition that includes production of alcohol esters by esterification of product alcohol in a fermentation medium with a carboxylic acid (e.g., fatty acid) and a catalyst (e.g., lipase) capable of esterifying the product alcohol, such as butanol, with the carboxylic acid to form the alcohol esters. The alcohol esters can be extracted from the fermentation medium, and the product alcohol recovered from the alcohol esters. The carboxylic acid can also serve as an extractant for removal of the alcohol esters from the fermentation medium.

Claims

1. A method for producing butyl esters comprising:

contacting butanol produced in a fermentation process with at least one exogenous carboxylic acid and at least one extracellular enzyme capable of esterifying the carboxylic acid with the butanol to form butyl esters of the carboxylic acid;

wherein the carboxylic acid in the fermentation process is present at a concentration sufficient to produce a two-phase mixture.

23. The method of claim 1, wherein the carboxylic acid comprises fatty acids.

24. The method of claim 1, wherein the enzyme is an esterase, lipase, phospholipase, lysophospholipase, or mixture thereof.

2. A method comprising:

(a) contacting butanol produced in a fermentation process with at least one exogenous carboxylic acid and at least one extracellular enzyme capable of esterifying the carboxylic acid with the butanol to form butyl esters of the carboxylic acid;

wherein the carboxylic acid in the fermentation process is present at a concentration sufficient to produce a two-phase mixture comprising an aqueous phase and a butyl ester-containing organic phase;

(b) separating the butyl ester-containing organic phase from the aqueous phase; and

(c) recovering butanol from the butyl esters.

25. The method of claim 2, wherein the carboxylic acid comprises fatty acids.

26. The method of claim 2, wherein the enzyme is an esterase, lipase, phospholipase, lysophospholipase, or mixture thereof.

3. A method for producing butanol and butyl esters from a feedstock comprising:

(a) providing a feedstock;

(b) liquefying the feedstock to create a liquefied biomass comprising oligosaccharides;

(c) separating the feedstock slurry to produce a product comprising an aqueous stream, an oil stream, and solids;

(d) adding the aqueous stream to a fermentation vessel containing a fermentation broth

(e) saccharifying the aqueous stream;

(f) fermenting the saccharified aqueous stream to produce butanol and concurrently contacting the butanoi with at least one exogenous carboxylic acid and at least one extracellular enzyme capable of esterifying the carboxylic acid with the butanol to form butyl esters of the carboxylic acid wherein the carboxylic acid is present at a concentration sufficient to produce a two-phase mixture;

(g) separating the butyl ester-containing organic phase from the aqueous phase; and

(h) recovering butanol from the butyl esters;

and optionally steps (e) and (f) occur concurrently.

4. The method of claim 3, wherein the feedstock in the fermentation process comprises one or more fermentable sugars.

5. The method of claim 3, wherein the feedstock in the fermentation process comprises one or more fermentable sugars derived from corn grain, corn cobs, crop residues such as corn husks, corn stover, grasses, wheat, rye, wheat straw, barley, barley straw, hay, rice straw, switchgrass, waste paper, sugar cane bagasse, sorghum, sugar cane, soy, components obtained from milling of grains, cellulosic material, lignocellulosic material, trees, branches, roots, leaves, wood chips, sawdust, shrubs and bushes, vegetables, fruits, flowers, animal manure, and mixtures thereof.

6. The method of claim 3, further comprising

obtaining an oil from the oil stream and converting at least a portion of the oil into carboxylic acid.

7. The method of claim 3, wherein the feedstock slurry is separated by decanter bowl centrifugation, tricanter centrifugation, disk stack centrifugation, filtering centrifugation, decanter centrifugation, filtration, vacuum filtration, beltfilter, pressure filtration, screen filtration, screen separation, grating, porous grating, flotation, hydroclone, filter press, screwpress, gravity settler, vortex separator, or combination thereof.

8. The method of claim 3, wherein the carboxylic acid comprises fatty acids.

9. The method of claim 3, wherein the carboxylic acid comprises 12 to 22 carbons.

10. The method of claim 3, further comprising:

adding additional carboxylic acid to the fermentation vessel.

11. The method of claim 10, wherein the oil is converted to carboxylic acid after the step of adding the additional carboxylic acid.

12. The method of claim 3, wherein the carboxylic acid is corn oil fatty acid, soya oil fatty acid, or a mixture of corn oil fatty acid and soya oil fatty acid.

13. The method of claim 3, wherein the oil comprises glycerides and the one or more extracellular enzymes hydrolyze the glycerides into fatty acids.

14. The method of claim 3, wherein the extracellular enzyme is an esterase, lipase, phospholipase, or lysophospholipase.

15. The method of claim 3, wherein recovering butanol from the butyl esters comprises hydrolyzing the esters into carboxylic acid and butanol.

16. The method of claim 15, wherein the butyl esters are hydrolyzed in the presence of a hydrolysis catalyst.

17. The method of claim 16, wherein the hydrolysis catalyst comprises an acid catalyst, an organic acid, a water soluble acid, water insoluble acid, or base.

18. The method of claim 16, wherein the hydrolysis catalyst comprises an enzyme capable of hydrolyzing the butyl esters to form a carboxylic acid and butanol.

19. The method of claim 18, wherein the enzyme is an esterase, lipase, phospholipase, or lysophospholipase.

20. The method of claim 3, wherein recovering butanol from the butyl esters comprises transesterifying the butyl esters into butanol and other fatty acid alkyl esters or acyl glycerides.

21. The method of claim 20, wherein the other fatty acid alkyl esters comprise fatty acid methyl esters, fatty acid ethyl esters, or fatty acid propyl esters.

22. The method of claim 3, wherein the solids are processed to form to an animal feed product.