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

• US 9,175,315 B2
• Filed: 06/17/2011
• Issued: 11/03/2015
• Est. Priority Date: 06/18/2010
• Status: Active Grant

• Current Assignee: Gevo Incorporated
• Original Assignee: Butamax(TM) Advanced Biofuels LLC (BP PLC)
• Inventors: Anton, Douglas Robert, Bazzana, Stephane Francois, Dicosimo, Robert, Diner, Bruce A, Grady, Michael Charles, Roesch, Brian Michael, Burlew, Keith H, Cirakovic, Jelena, Woerner, Francis J
• Primary Examiner(s): CHOWDHURY, IQBAL HOSSAIN
• Application Number:
  US13/162,868
• Publication Number:
  US 20120156738A1
• Time in Patent Office: 1,600 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: A23K 10/38 from distillers' or brewers' waste
• CPC Class Codes: B01D 11/0492 Applications, solvents used
• CPC Class Codes: B01D 21/26 Separation of sediment aided by centrifugal force or centripetal forcecentrifuges B04B; cyclones B04C
• CPC Class Codes: B01D 21/262 by using a centrifuge
• CPC Class Codes: B01D 3/002 by continuous methods
• CPC Class Codes: C07C 29/86 by liquid-liquid treatment
• CPC Class Codes: C11B 1/025 by enzymes or microorganisms, living or dead
• CPC Class Codes: C11B 13/00 Recovery of fats, fatty oils or fatty acids from waste materials
• CPC Class Codes: C12F 3/10 from distillery slops
• CPC Class Codes: C12M 1/00 Apparatus for enzymology or microbiology
• CPC Class Codes: C12M 21/12 for producing fuels or solvents C12M21/04 takes precedence; liquid carbonaceous fuels C10L1/00, solid fuels C10L5/00
• CPC Class Codes: C12M 45/04 Phase separators; Separation of non fermentable material; Fractionation
• CPC Class Codes: C12M 45/09 by enzymatic treatment
• CPC Class Codes: C12N 1/14 Fungi culture of mushrooms A01G18/00; as new plants A01H15/00; Culture media therefor
• CPC Class Codes: C12N 15/00 Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor mutants or genetically engineered microorganisms, per se C12N1/00, C12N5/00, C12N7/00; new plants per se A01H; plant reproduction by tissue culture techniques A01H4/00; new animals per se A01K67/00; use of medicinal preparations containing genetic material which is inserted into cells of the living body to treat genetic diseases, gene therapy A61K48/00
• CPC Class Codes: C12P 7/16 Butanols
• CPC Class Codes: C12P 7/18 polyhydric
• CPC Class Codes: C12P 7/6418 by hydrolysis of fatty acid esters
• CPC Class Codes: Y02E 50/10 Biofuels, e.g. bio-diesel
• CPC Class Codes: Y02W 30/74 Recovery of fats, fatty oils, fatty acids or other fatty substances, e.g. lanolin or waxes

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:

a) providing an oil and converting at least a portion of the oil into carboxylic acid by contacting the oil with one or more enzymes, wherein the one or more enzymes are selected from an esterase, lipase, phospholipase, lysophospholipase, or a mixture thereof;

b) providing the converted carboxylic acid to a fermentation process; and

c) contacting butanol produced in the fermentation process with the provided carboxylic acid and at least one catalyst capable of esterifying the carboxylic acid with the butanol to form butyl esters of the carboxylic acid, wherein the catalyst is an enzyme selected from an esterase, lipase, phospholipase, lysophospholipase, or a mixture thereof;

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

2. The method of claim 1, wherein the production of butanol and the production of butyl esters occur simultaneously or sequentially.

3. The method of claim 1, wherein a feedstock in the fermentation process comprises one or more fermentable sugars.

4. The method of claim 2, 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.

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

6. The method of claim 1, wherein the carboxylic acid comprises 12 to 22 carbons.

7. The method of claim 1, wherein the carboxylic acid is a mixture of carboxylic acids.

8. The method of claim 1, wherein the butyl esters of the carboxylic acid are butyl esters of fatty acids.

9. 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 an aqueous stream comprising oligosaccharides, an oil stream, and solids;

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

(e) saccharifying the oligosaccharides of the aqueous stream;

(f) fermenting the products of the oligosaccharide saccharification present in the aqueous stream to produce butanol and concurrently contacting the butanol with at least one carboxylic acid and at least one catalyst capable of esterifying the carboxylic acid with the butanol to form butyl esters of the carboxylic acid, wherein the catalyst is an enzyme selected from an esterase, lipase, phospholipase, lysophospholipase, or a mixture thereof,

wherein the carboxylic acid is present at a concentration sufficient to produce a two-phase mixture;

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

11. The method of claim 9, wherein the carboxylic acid comprises fatty acids.

12. The method of claim 9, further comprising

converting at least a portion of the oil into carboxylic acid by contacting the oil with one or more enzymes, wherein the one or more enzymes are selected from an esterase, lipase, phospholipase, lysophospholipase, or a mixture thereof.

13. The method of claim 12, wherein the carboxylic acid is added to the fermentation vessel.

14. The method of claim 12 wherein the carboxylic acid comprises fatty acids.

15. The method of claim 9, further comprising:

adding the oil to the fermentation vessel and converting at least a portion of the oil into carboxylic acid by contacting the oil with one or more enzymes, wherein the one or more enzymes are selected from an esterase, lipase, phospholipase, lysophospholipase, or a mixture thereof.

10. 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 stream comprising oligosaccharides and oil, and solids;

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

(e) saccharifying the oligosaccharides of the stream;

(f) fermenting the products of the oligosaccharide saccharification present in the stream to produce butanol and concurrently contacting the butanol with at least one carboxylic acid and at least one catalyst capable of esterifying the carboxylic acid with the butanol to form butyl esters of the carboxylic acid, wherein the catalyst is an enzyme selected from an esterase, lipase, phospholipase, lysophospholipase, or a mixture thereof,

wherein the carboxylic acid is present at a concentration sufficient to produce a two-phase mixture;

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

16. The method of claim 10, wherein the carboxylic acid comprises fatty acids.

17. The method of claim 10, further comprising

converting at least a portion of the oil into carboxylic acid by contracting the oil with one or more enzymes, wherein the one or more enzymes are selected from an esterase, lipase, phospholipase, lysophospholipase, or a mixture thereof.

18. The method of claim 17, wherein the carboxylic acid is added to the fermentation vessel.

19. The method of claim 17, wherein the carboxylic acid comprises fatty acids.