# US 9,040,263 B2 · Production of alcohol esters and in situ product removal during alcohol fermentation

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- Number: US 9,040,263 B2
- Document ID: US9040263B2
- Status: Granted
- Kind: B2
- Application number: 13/193,147
- Filed: 2011-07-28
- Published: 2012-08-16
- Granted: 2015-05-26
- Earliest claimed: 2010-07-28
- Assignees: Butamax Advanced Biofuels LLC
- Applicants: Douglas Robert Anton; Stephane Francois Bazzana; Keith H. Burlew; Jelena Cirakovic; Robert Dicosimo; Bruce A. Diner; Michael Charles Grady; Brian Michael Roesch; Francis J. Woerner
- Inventors: Douglas Robert Anton; Stephane Francois Bazzana; Keith H. Burlew; Jelena Cirakovic; Robert Dicosimo; Bruce A. Diner; Michael Charles Grady; Brian Michael Roesch; Francis J. Woerner
- Web page: https://patentgrep.com/patent/US9040263B2

## CPC

- A23K 10/12: by fermentation of natural products, e.g. of vegetable material, animal waste material or biomass
- A23K 10/38: from distillers' or brewers' waste
- C12P 7/16: Butanols
- C12P 7/62: Carboxylic acid esters
- C12P 7/6458: by transesterification, e.g. interesterification, ester interchange, alcoholysis or acidolysis
- C12P 7/649: Biodiesel, i.e. fatty acid alkyl esters
- C12P 2203/00: Fermentation products obtained from optionally pretreated or hydrolyzed cellulosic or lignocellulosic material as the carbon source
- Y02E 50/10: Biofuels, e.g. bio-diesel
- Y02P 60/87: Re-use of by-products of food processing for fodder production
- A23K: FODDER
- C12P: FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE {(brewing of beer C12C; producing vinegar C12J; producing specific peptides or proteins C07K; producing enzymes C12N9/00; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; measuring or testing processes involving enzymes or microorganisms C12Q; measuring or testing processes involving nucleic acid amplification reactions C12Q1/6844; fermentation processes to form a food composition, A21 or A23; compounds in general, see the relevant compound class, e.g. C01, C07)}
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## 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

### Claim 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.

### Claim 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.

### Claim 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.

### Claim 4 (depends on 3)

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

### Claim 5 (depends on 3)

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.

### Claim 6 (depends on 3)

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.

### Claim 7 (depends on 3)

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.

### Claim 8 (depends on 3)

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

### Claim 9 (depends on 3)

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

### Claim 10 (depends on 3)

The method of claim 3, further comprising:
adding additional carboxylic acid to the fermentation vessel.

### Claim 11 (depends on 10)

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

### Claim 12 (depends on 3)

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.

### Claim 13 (depends on 3)

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

### Claim 14 (depends on 3)

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

### Claim 15 (depends on 3)

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

### Claim 16 (depends on 15)

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

### Claim 17 (depends on 16)

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.

### Claim 18 (depends on 16)

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.

### Claim 19 (depends on 18)

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

### Claim 20 (depends on 3)

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.

### Claim 21 (depends on 20)

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.

### Claim 22 (depends on 3)

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

### Claim 23 (depends on 1)

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

### Claim 24 (depends on 1)

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

### Claim 25 (depends on 2)

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

### Claim 26 (depends on 2)

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