# US 6,723,863 B2 · Methods for the preparation of propylene glycol fatty acid esters

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- Number: US 6,723,863 B2
- Document ID: US6723863B2
- Status: Granted
- Kind: B2
- Application number: 10/213,434
- Filed: 2002-08-07
- Published: 2003-03-20
- Granted: 2004-04-20
- Earliest claimed: 2001-08-09
- Assignees: Archer Daniels Midland Company
- Inventors: Inmok Lee; George Poppe
- Web page: https://patentgrep.com/patent/US6723863B2

## CPC

- C11C 3/10: Ester interchange
- C07C 67/03: by reacting an ester group with a hydroxy group
- C11C 3/003: {by esterification of fatty acids with alcohols (C11C3/02 takes precedence)}
- 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

A process of producing a light-colored, high-monoester mixture from a polyol and an oil is provided wherein the process eliminates the use of organic solvents, multiple water washings and/or molecular distillation. The reactants, a polyol and an oil, described herein, condense in the presence of a catalyst, described herein, at a temperature range from about 180° C. to about 280° C. under an inert atmosphere or the vapor pressure of the polyol with a pressure of about 0 to about 500 psig to yield a monoester mixture possessing a desirable monoester composition and color. The present process yields a final product similar to that of processes which require the use of solvents, multiple water washings and/or molecular distillation.

## Claims

### Claim 1

A process of producing a monoester mixture comprising reacting a polyol with a triglyceride oil in the presence of a catalyst at a temperature range from about 180° C. to about 280° C. under an inert atmosphere with a pressure from about 0 to about 500 psig wherein a monoester mixture is produced.

### Claim 2 (depends on 1)

The process of claim 1, wherein said produced mono-ester mixture is purified, the process comprising the steps of:
a) neutralizing said catalyst,
b) separating excess polyol, and
c) deodorizing residual product.

### Claim 3 (depends on 2)

The process of claim 2, wherein said purification further comprises the treatment of said deodorized residual product to remove salts.

### Claim 4 (depends on 1)

The process of claim 1, wherein said triglyceride oil is selected from the group consisting of: vegetable oils, fish oils, animal oils or transgenically-modified plant oils, and derivatives and mixtures thereof.

### Claim 5 (depends on 4)

The process of claim 4, wherein said vegetable oils are comprised of soybean oil, linseed oil, sunflower oil, corn oil, canola oil, rapeseed oil, palm kernel oil, cottonseed oil, peanut oil, coconut oil, palm oil, tung oil or safflower oil.

### Claim 6 (depends on 1)

The process of claim 1, wherein said triglyceride oil is soybean oil.

### Claim 7 (depends on 4)

The process of claim 4, wherein said triglyceride oil is fully hydrogenated.

### Claim 8 (depends on 7)

The process of claim 7, wherein said triglyceride oil is a vegetable oil.

### Claim 9 (depends on 8)

The process of claim 8, wherein said triglyceride oil is soybean oil.

### Claim 10 (depends on 1)

The process of claim 1, wherein said produced monoester mixture has a Lovibond color of less than 2 Red.

### Claim 11 (depends on 1)

The process, of claim 1, wherein said catalyst comprises an alkali metal or alkali earth metal salt of a mono- or di-carboxylic acid.

### Claim 12 (depends on 1)

The process of claim 1, wherein said catalyst comprises sodium or potassium salt of a mono- or di-carboxylic acid.

### Claim 13 (depends on 11)

The process of claim 11, wherein said mono- or di-carboxylic acid is selected from the group consisting of: acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, eicosanoic acid, oleic acid, linoleic acid, linolenic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, maleic acid and benzoic acid.

### Claim 14 (depends on 12)

The process of claim 12, wherein said catalyst is potassium acetate.

### Claim 15 (depends on 1)

The process of claim 1, wherein said catalyst is present in a concentration between about 0.001% to about 10%, based on weight amount of the oil in the reaction.

### Claim 16 (depends on 15)

The process of claim 15, wherein said concentration is between about 0.01% to about 1.0%.

### Claim 17 (depends on 2)

The process of claim 2, wherein said step of neutralizing catalyst comprises adding sufficient amount of an acid to neutralize said catalyst.

### Claim 18 (depends on 17)

The process of claim 17, wherein said acid is phosphoric acid.

### Claim 19 (depends on 1)

The process of claim 1, wherein said polyol is a dihydric alcohol.

### Claim 20 (depends on 19)

The process of claim 19, wherein said dihydric alcohol is propylene glycol.

### Claim 21 (depends on 1)

The process of claim 1, wherein the molar ratio of polyol to oil is about 8:1 to about 14:1.

### Claim 22 (depends on 21)

The process of claim 21, wherein said molar ratio is about 12:1.

### Claim 23 (depends on 1)

The process of claim 1, wherein said temperature range is from about 180° to about 240° C.

### Claim 24 (depends on 23)

The process of claim 23, wherein said pressure is from about 30 to about 400 psig.

### Claim 25 (depends on 24)

The process of claim 24 wherein, said pressure is from about 100 to about 400 psig.

### Claim 26 (depends on 1)

The process of claim 1 wherein said inert atmosphere is selected from the group consisting of N2, CO2 and Ar.

### Claim 27 (depends on 1)

The process of claim 1 wherein said inert atmosphere is CO2.

### Claim 28

A process of producing a monoester mixture comprising,
a. forming a mixture by agitating a polyol with a triglyceride oil in the presence of a catalyst,
b. subjecting said mixture to a vacuum,
c. sealing reactor and heating the mixture in a vacuum to a temperature from about 180° C. to about 280° C., wherein a vapor pressure is generated, and a monoester mixture is produced.

### Claim 29 (depends on 28)

The process of claim 28 further comprising the steps of,
i. cooling the mixture,
ii. neutralizing said catalyst,
iii. collecting the monoester mixture produced from said mixture, and
iv. stripping the monoester mixture at a temperature from about 50° C. to about 150° C. under vacuum.

### Claim 30 (depends on 28)

The process of claim 28, wherein the triglyceride oil is selected from the group consisting of: vegetable oils, fish oils, animal oils or transgenically-modified plant oils, and derivatives and mixtures thereof.

### Claim 31 (depends on 30)

The process of claim 30, wherein said vegetable oils are comprised of soybean oil, linseed oil, sunflower oil, corn oil, canola oil, rapeseed oil, palm kernel oil, cottonseed oil, peanut oil, coconut oil, palm oil, tung oil or safflower oil.

### Claim 32 (depends on 31)

The process of claim 31, wherein the vegetable oil is soybean oil.

### Claim 33 (depends on 28)

The process of claim 28, wherein the triglyceride oil is fully hydrogenated.

### Claim 34 (depends on 33)

The process of claim 33, wherein the triglyceride oil is a vegetable oil.

### Claim 35 (depends on 34)

The process of claim 34, wherein said vegetable oil is soybean oil.

### Claim 36 (depends on 10, 28)

The process of one of claims 10 or 28, wherein said produced monoester mixture has a Lovibond color of less than 2 Red.

### Claim 37 (depends on 28)

The process of claim 28, wherein said catalyst comprises an alkali metal or alkali earth metal salt of a mono- or di-carboxylic acid.

### Claim 38 (depends on 28)

The process of claim 28, wherein said catalyst comprises sodium or potassium salt of a mono- or di-carboxylic acid.

### Claim 39 (depends on 38)

The process of claim 38, wherein said mono- or di-carboxylic acid is selected from the group consisting of: acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, eicosanoic acid, oleic acid, linoleic acid, linolenic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, maleic acid and benzoic acid.

### Claim 40 (depends on 39)

The process of claim 39, wherein said catalyst is potassium acetate.

### Claim 41 (depends on 28)

The process of claim 28, wherein said catalyst is present in a concentration between about 0.001% to about 10%, based on weight amount of the oil in the reaction.

### Claim 42 (depends on 41)

The process of claim 41, wherein said concentration is between about 0.01% to about 1.0%.

### Claim 43 (depends on 29)

The process of claim 29, wherein said step of neutralizing catalyst comprises adding sufficient amount of an acid to neutralize said catalyst.

### Claim 44 (depends on 43)

The process of claim 43, wherein said acid is phosphoric acid.

### Claim 45 (depends on 28)

The process of claim 28, wherein said polyol is a dihydric alcohol.

### Claim 46 (depends on 45)

The process of claim 45, wherein said dihydric alcohol is propylene glycol.

### Claim 47 (depends on 28)

The process of claim 28, wherein the molar ratio of polyol to oil is about 8:1 to about 14:1.

### Claim 48 (depends on 47)

The process of claim 47, wherein said molar ratio is about 12:1.

### Claim 49 (depends on 28)

The process of claim 28, wherein said vacuum is from about 1 to about 30 inches of Hg at a temperature between about 5° C. and about 120° C.

### Claim 50 (depends on 28)

The process of claim 28, wherein said vapor pressure is from about 0 to about 60 psig.

### Claim 51 (depends on 28)

The process of claim 28, wherein the triglyceride oil is partially hydrogenated.