# US 7,612,221 B2 · Production of fatty acid alkyl esters

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- Number: US 7,612,221 B2
- Document ID: US7612221B2
- Status: Granted
- Kind: B2
- Application number: 11/337,458
- Filed: 2006-01-23
- Published: 2006-07-13
- Granted: 2009-11-03
- Earliest claimed: 2002-04-02
- Assignees: The United States of America as represented by the Secretary of Agriculture
- Inventors: Michael J. Haas; William N. Marmer; Thomas A. Foglia
- Web page: https://patentgrep.com/patent/US7612221B2

## CPC

- C11C 3/003: {by esterification of fatty acids with alcohols (C11C3/02 takes precedence)}
- C07C 67/03: by reacting an ester group with a hydroxy group
- C11C: FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The present invention relates to a method for producing fatty acid alkyl esters, involving transesterifying a feedstock containing lipid-linked fatty acids with an alcohol and an alkaline catalyst to form fatty acid alkyl esters. The feedstock has not been previously treated to release the lipid components of said feedstock, or the feedstock has been previously treated to release lipid components and the feedstock contains residual lipids (e.g., <about 30% of the original content of lipids).

## Claims

### Claim 1

A method for producing fatty acid alkyl esters, comprising transesterifying a feedstock containing lipid-linked fatty acids with an alcohol and an alkaline catalyst to form fatty acid alkyl esters, wherein (I) said feedstock has not been previously treated to release the lipid components of said feedstock and the yield of said fatty acid alkyl esters is at least 90% of theoretical maximum or (ii) said feedstock has been previously treated to release lipid components and said feedstock contains residual lipids and the yield of said fatty acid alkyl esters is at least 75% of theoretical maximum; and wherein said feedstock excludes crude or refined isolated fats and oils from plant seeds or fruits or crude or refined animal products.

### Claim 2 (depends on 1)

The method according to claim 1, wherein said feedstock has not been previously treated to release the lipid components of said feedstock.

### Claim 3 (depends on 2)

The method according to claim 2, wherein said feedstock is a seed or fruit.

### Claim 4 (depends on 2)

The method according to claim 2, wherein said feedstock is selected from the group consisting of soy, coconut, corn, cotton, flax, palm, rapeseed/canola, safflower, sunflower, distiller's dried grains with or without solubles, and mixtures thereof.

### Claim 5 (depends on 2)

The method according to claim 2, wherein said feedstock is soy.

### Claim 6 (depends on 2)

The method according to claim 2, wherein said feedstock is coconut or palm.

### Claim 7 (depends on 2)

The method according to claim 2, wherein said feedstock is rapeseed/canola.

### Claim 8 (depends on 2)

The method according to claim 2, wherein said feedstock is distiller's dried grains with or without solubles.

### Claim 9 (depends on 2)

The method according to claim 2, wherein said feedstock has been pre-treated to allow access of said alcohol and said alkaline catalyst to the interior of said feedstock.

### Claim 10 (depends on 1)

The method according to claim 1, wherein said feedstock has been previously treated to release lipid components and said feedstock contains residual lipids.

### Claim 11 (depends on 10)

The method according to claim 10, wherein said feedstock has been previously treated to release lipid components and said feedstock contains < about 30% of the original content of lipids.

### Claim 12 (depends on 10)

The method according to claim 10, wherein said feedstock has been previously treated to release lipid components and said feedstock contains < about 25% of the original content of lipids.

### Claim 13 (depends on 10)

The method according to claim 10, wherein said feedstock has been previously treated to release lipid components and said feedstock contains < about 20% of the original content of lipids.

### Claim 14 (depends on 10)

The method according to claim 10, wherein said feedstock has been previously treated to release lipid components and said feedstock contains < about 15% of the original content of lipids.

### Claim 15 (depends on 10)

The method according to claim 10, wherein said feedstock is of plant or animal origin.

### Claim 16 (depends on 10)

The method according to claim 10, wherein said feedstock is selected from the group consisting of soy meal, coconut meal, corn meal, cotton meal, flax meal, palm meal, rapeseed/canola meal, safflower meal, sunflower meal, meat and bone meal, and mixtures thereof.

### Claim 17 (depends on 10)

The method according to claim 10, wherein said feedstock is meat and bone meal.

### Claim 18 (depends on 10)

The method according to claim 10, wherein said feedstock is soy meal.

### Claim 19 (depends on 1)

The method according to claim 1, wherein said feedstock excludes crude or refined isolated fats and oils from soy, coconut, corn, cotton, flax, palm, rapeseed/canola, safflower, sunflower, or tallow, lard or fish oil.

### Claim 20 (depends on 1)

The method according to claim 1, wherein said fatty acid alkyl esters are fatty acid methyl esters or fatty acid ethyl esters.

### Claim 21 (depends on 1)

The method according to claim 1, wherein said alcohol is a C1-4 alcohol.

### Claim 22 (depends on 1)

The method according to claim 1, wherein said alcohol is selected from the group consisting of methanol, ethanol, isopropanol, and mixtures thereof.

### Claim 23 (depends on 1)

The method according to claim 1, wherein said alkaline catalyst is selected from the group consisting of Group I or Group II hydroxides, alkoxides, or carbonates, or mixtures thereof.

### Claim 24 (depends on 1)

The method according to claim 1, wherein said alkaline catalyst is selected from the group consisting of NaOH, KOH, sodium methylate, potassium methylate, sodium carbonate, potassium carbonate, or mixtures thereof.

### Claim 25 (depends on 1)

The method according to claim 1, wherein the molar ratio of said alcohol: said alkaline catalyst is about ≦500:1.

### Claim 26 (depends on 1)

The method according to claim 1, wherein the concentration of said alkaline catalyst is about ≧0.05N.

### Claim 27 (depends on 1)

The method according to claim 1, wherein said method utilizes about 0.04-about 25 ml of said alcohol per gram of said feedstock.

### Claim 28 (depends on 1)

The method according to claim 1, wherein said method utilizes a molar ratio of said alcohol: said feedstock glyceride content of 3.38-2178:1.

### Claim 29 (depends on 1)

The method according to claim 1, wherein said method utilizes about 2-about 10 ml of said alcohol per gram of said feedstock.

### Claim 30 (depends on 1)

The method according to claim 1, wherein said method utilizes about 0.02-about 0.4 molar of alkali in said alcohol.

### Claim 31 (depends on 1)

The method according to claim 1, wherein the reaction time of said method is about 1-about 12 hours.

### Claim 32 (depends on 1)

The method according to claim 1, wherein said method is conducted at a reaction temperature of about 20°-about 70° C.

### Claim 33 (depends on 1)

The method according to claim 1, wherein said fatty acid alkyl esters contain less than about 1000 mg free fatty acids/g fatty acid alkyl esters.

### Claim 34 (depends on 1)

The method according to claim 1, wherein said fatty acid alkyl esters contain less than about 5% weight basis of unreacted triacylglycerols, unreacted diacylglycerides, and unreacted monoacylglycerides.

### Claim 35 (depends on 1)

The method according to claim 1, wherein the yield of said fatty acid alkyl esters in (I) is at least about 80% of theoretical maximum.

### Claim 36 (depends on 1)

The method according to claim 1, wherein the yield of said fatty acid alkyl esters in (I) is at least about 85% of theoretical maximum.

### Claim 37 (depends on 1)

The method according to claim 1, wherein the yield of said fatty acid alkyl esters is at least about 90% of theoretical maximum.

### Claim 38 (depends on 1)

The method according to claim 1, wherein the yield of said fatty acid alkyl esters is at least about 95% of theoretical maximum.

### Claim 39 (depends on 1)

The method according to claim 1, wherein the yield of said fatty acid alkyl esters is at least about 96% of theoretical maximum.

### Claim 40 (depends on 1)

The method according to claim 1, wherein the yield of said fatty acid alkyl esters is at least about 97% of theoretical maximum.

### Claim 41 (depends on 1)

The method according to claim 1, wherein the yield of said fatty acid alkyl esters is at least about 98% of theoretical maximum.

### Claim 42 (depends on 1)

The method according to claim 1, wherein the yield of said fatty acid alkyl esters is at least about 99% of theoretical maximum.

### Claim 43 (depends on 1)

The method according to claim 1, wherein the yield of said fatty acid alkyl esters is at least about 100% of theoretical maximum.

### Claim 44

A method for producing fatty acid alkyl esters, comprising transesterifying a feedstock containing lipid-linked fatty acids with an alcohol and an alkaline catalyst to form fatty acid alkyl esters, wherein said feedstock has not been previously treated to release the lipid components of said feedstock and the yield of said fatty acid alkyl esters is at least 90% of theoretical maximum; and wherein said feedstock excludes crude or refined isolated fats and oils from plant seeds or fruits or crude or refined animal products.

### Claim 45

A method for producing fatty acid alkyl esters, comprising transesterifying a feedstock containing lipid-linked fatty acids with an alcohol and an alkaline catalyst to form fatty acid alkyl esters, wherein said feedstock has been previously treated to release lipid components and said feedstock contains residual lipids and the yield of said fatty acid alkyl esters is at least 75% of theoretical maximum; and wherein said feedstock excludes crude or refined isolate fats and oils from plant seeds or fruits or crude or refined animal products.

### Claim 46 (depends on 1)

The method according to claim 1, wherein said method is conducted at a reaction temperature of about 20°-about 40° C.

### Claim 47 (depends on 1)

The method according to claim 1, wherein said method is conducted at a reaction temperature of about 20°-about 30° C.

### Claim 48 (depends on 1)

The method according to claim 1, wherein said method is conducted at a reaction temperature of 20°-40° C.

### Claim 49 (depends on 1)

The method according to claim 1, wherein said method is conducted at a reaction temperature of 20°-30° C.