# US 2014/0154393 A1 · Conjugated linoleic acid rich vegetable oil production from linoleic rich oils by heterogeneous catalysis

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- Number: US 2014/0154393 A1
- Document ID: US20140154393A1
- Status: Published application
- Kind: A1
- Application number: 13/692,619
- Filed: 2012-12-03
- Published: 2014-06-05
- Earliest claimed: 2012-12-03
- Assignees: Board of Trustees of the University of Arkansas
- Applicants: Board of Trustees of the University of Arkansas
- Inventors: Andrew Proctor; Utkarsh Shah
- Web page: https://patentgrep.com/patent/US20140154393A1

## CPC

- C11C 3/14: by isomerisation {(isomerisation induced by hydrogenation C11C3/12)}
- A23D 7/0053: {Compositions other than spreads}
- A23D 7/0056: {Spread compositions}
- C11C 3/00: Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom (sulfonated fats or oils C07C309/62; factice C08H; drying oils C09F)
- 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
- A23D: EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS (preservation thereof A23B20/00; production, refinement or preservation of animal or vegetable fats or oils C11B, C11C)

## Abstract

The invention is generally directed to conjugated linoleic acid (CLA)-rich vegetable oil production from linoleic rich oils by heterogeneous catalysis. A heterogeneous catalytic vacuum distillation process is used under high temperature conditions to isomerize linoleic acid in triacylglyceride vegetable oils to CLA to produce CLA-rich oils. After processing, the catalyst may be removed by filtration or centrifugation to obtain high quality, CLA-rich oils. The CLA-rich oils may then serve as a potent and bioactive nutraceutical and can be incorporated into various food products, such as a CLA-rich dressing, margarine or chips.

## Claims

### Claim 1

A process for producing conjugated linoleic acid-rich oil, said process comprising the steps of:
a. mixing a linoleic acid-rich oil with a catalytic amount of a transition metal to form an oil-catalyst mixture; and
b. catalysis of said oil-catalyst mixture to produce said conjugated linoleic acid-rich oil.

### Claim 2 (depends on 1)

The process of claim 1 further comprising the step of extracting said metal from said conjugated linoleic acid-rich oil.

### Claim 3 (depends on 2)

The process of claim 2 further comprising the step of extracting said metal from said conjugated linoleic acid-rich oil via filtration or centrifugation.

### Claim 4 (depends on 1)

The process of claim 1 wherein said linoleic acid-rich oil is a triacylglyceride vegetable oil.

### Claim 5 (depends on 4)

The process of claim 4 wherein said triacylglyceride vegetable oil is selected from the group consisting of soy, sunflower, corn, cottonseed or peanut oil.

### Claim 6 (depends on 44)

The process of claim 44 wherein said transition metal is selected from the group consisting of ruthenium, rhodium, molybdenum, palladium, gold, silver, copper, iron, manganese or nickel.

### Claim 7 (depends on 6)

The process of claim 6 wherein said transition metal is ruthenium or nickel.

### Claim 8 (depends on 1)

The process of claim 1 wherein said catalysis step further comprises catalysis of said oil-catalyst mixture in low pressure conditions and high temperature conditions to produce said conjugated linoleic acid-rich oil.

### Claim 9 (depends on 8)

The process of claim 8 wherein said catalysis step further comprises catalysis of said oil-catalyst mixture in low pressure conditions and high temperature conditions for up to approximately 192 minutes to produce said conjugated linoleic acid-rich oil.

### Claim 10 (depends on 9)

The process of claim 9 wherein said catalysis step further comprises catalysis of said oil-catalyst mixture in low pressure conditions and high temperature conditions for between approximately 108 minutes and approximately 180 minutes to produce said conjugated linoleic acid-rich oil.

### Claim 11 (depends on 8)

The process of claim 8 wherein said low pressure further comprise pressure conditions between approximately 1 mm Hg and approximately 2 mm Hg.

### Claim 12 (depends on 8)

The process of claim 8 wherein said high temperature conditions further comprise temperature conditions between approximately 197° C. and approximately 282° C.

### Claim 13 (depends on 12)

The process of claim 12 wherein said high temperature conditions are between approximately 210° C. and approximately 240° C.

### Claim 14 (depends on 1)

The process of claim 1 wherein said catalysis step further comprises catalysis of said oil-catalyst mixture in pressure conditions between approximately 1 mm Hg and approximately 2 mm Hg and temperature conditions between approximately 197° C. and approximately 282° C. to produce said conjugated linoleic acid-rich oil.

### Claim 15 (depends on 1)

The process of claim 1 wherein said catalysis step further comprises heterogeneous catalysis via vacuum distillation of said oil-catalyst mixture in a continuous flow bath at a temperature range between approximately 197° C. and approximately 282° C.

### Claim 16 (depends on 1)

The process of claim 1 wherein said catalysis step further comprises heterogeneous catalysis of said oil-catalyst mixture in a continuous flow bath at a temperature range between approximately 197° C. and approximately 282° C. and at a pressure range between 1 mm Hg and approximately 2 mm Hg.

### Claim 17 (depends on 1)

The process of claim 1 wherein said catalysis step further comprises a two-phase catalysis of said oil-catalyst mixture at a temperature range of between approximately 210° C. and approximately 240° C. and at a pressure range between 1 mm Hg and approximately 2 mm Hg to produce said conjugated linoleic acid-rich oil.

### Claim 18 (depends on 17)

The process of claim 17 wherein said catalytic amount of said transition metal comprises between approximately 0.64% and approximately 1% of said transition metal.

### Claim 19 (depends on 1)

The process of claim 1 wherein said catalytic amount of said transition metal comprises between 0.21% to approximately 1% of said transition metal.

### Claim 20 (depends on 19)

The process of claim 19 wherein said catalytic amount of said transition metal is approximately 0.64% of a ruthenium catalyst or approximately 1% of a nickel catalyst.

### Claim 21

A process for enriching a linoleic acid-rich vegetable oil, said process comprising the step of distilling said linoleic acid-rich vegetable oil in the presence of a transition metal catalyst to produce a conjugated linoleic acid-rich oil.

### Claim 22 (depends on 21)

The process of claim 21 further comprising the step of extracting said metal catalyst from said conjugated linoleic acid-rich oil.

### Claim 23 (depends on 22)

The process of claim 22 further comprising the step of extracting said metal catalyst from said conjugated linoleic acid-rich oil via filtration or centrifugation.

### Claim 24 (depends on 21)

The process of claim 21 wherein said linoleic acid-rich oil is a triacylglyceride vegetable oil.

### Claim 25 (depends on 24)

The process of claim 24 wherein said triacylglyceride vegetable oil is selected from the group consisting of soy, sunflower, corn, cottonseed or peanut oil.

### Claim 26 (depends on 45)

The process of claim 45 wherein said metal catalyst is selected from the group consisting of ruthenium, rhodium, molybdenum, palladium, gold, silver, copper, iron, manganese or nickel.

### Claim 27 (depends on 21)

The process of claim 21 further comprises distilling said linoleic acid-rich vegetable oil with low pressure and high temperature to produce said conjugated linoleic acid-rich oil.

### Claim 28 (depends on 27)

The process of claim 27 wherein said step of distilling further comprises steam distilling said linoleic acid-rich vegetable oil for up to approximately 192 minutes to produce said conjugated linoleic acid-rich oil.

### Claim 29 (depends on 28)

The process of claim 28 wherein said step of steam distilling further comprises steam distilling said linoleic acid-rich vegetable oil with low pressure and high temperature for between approximately 108 minutes and approximately 180 minutes to produce said conjugated linoleic acid-rich oil.

### Claim 30 (depends on 27)

The process of claim 27 wherein said low pressure is substantially vacuum pressure.

### Claim 31 (depends on 27)

The process of claim 27 wherein said high temperature conditions further comprise a temperature between approximately 197° C. and approximately 282° C.

### Claim 32 (depends on 31)

The process of claim 31 wherein said high temperature conditions are between approximately 210° C. and approximately 240° C.

### Claim 33 (depends on 21)

The process of claim 21 wherein said distilling step further comprises distilling of said linoleic acid-rich vegetable oil at a pressure between approximately 1 mm Hg and approximately 2 mm Hg, at temperature between approximately 197° C. and approximately 282° C. to produce said conjugated linoleic acid-rich oil.

### Claim 34 (depends on 21)

The process of claim 21 wherein said distilling step further comprises vacuum steam distilling said linoleic acid-rich vegetable oil in a continuous flow bath at a temperature range between approximately 197° C. and approximately 282° C.

### Claim 35 (depends on 34)

The process of claim 34 wherein said distilling step further comprises vacuum steam distilling said linoleic acid-rich vegetable oil at a temperature range of between approximately 210° C. and approximately 240° C. for between approximately 108 minutes and approximately 180 minutes to produce said conjugated linoleic acid-rich oil.

### Claim 36 (depends on 21)

The process of claim 21 wherein said transition metal catalyst comprises between 0.21% to approximately 1% of said transition metal catalyst.

### Claim 37 (depends on 36)

The process of claim 36 wherein said transition metal catalyst is approximately 0.64% of a ruthenium catalyst or approximately 1% of a nickel catalyst.

### Claim 38 (depends on 21)

A conjugated linoleic acid-rich oil produced by the process of claim 21.

### Claim 39 (depends on 38)

The conjugated linoleic acid-rich oil of claim 38 comprising up to approximately 21% conjugated linoleic acid.

### Claim 40 (depends on 39)

The oil of claim 39 wherein said linoleic acid-rich oil is a triacylglyceride vegetable oil.

### Claim 41 (depends on 40)

The oil of claim 40 wherein said triacylglyceride vegetable oil is selected from the group consisting of soy, sunflower, corn, cottonseed or peanut oil.

### Claim 42 (depends on 21)

An enriched food product prepared using the conjugated linoleic acid-rich oil from the process of claim 21.

### Claim 43 (depends on 42)

The food product of claim 42 wherein said food product further comprises margarine, dressing or chips.

### Claim 44 (depends on 1)

The process of claim 1 wherein said transition metal is transition metal having a vacant 3d-orbital or a vacant 4d-orbital.

### Claim 45 (depends on 21)

The process of claim 21 wherein said transition metal catalyst is transition metal having a vacant 3d-orbital or a vacant 4d-orbital.