AU634476B2 - Recovery of carotenoids - Google Patents
Recovery of carotenoids Download PDFInfo
- Publication number
- AU634476B2 AU634476B2 AU36320/89A AU3632089A AU634476B2 AU 634476 B2 AU634476 B2 AU 634476B2 AU 36320/89 A AU36320/89 A AU 36320/89A AU 3632089 A AU3632089 A AU 3632089A AU 634476 B2 AU634476 B2 AU 634476B2
- Authority
- AU
- Australia
- Prior art keywords
- oil
- palm
- carotenes
- carotene
- esterified
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/02—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains containing only carbon and hydrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
Description
634476 COMMONWEALTH OF AUSTRALIA PATENTS ACT 1952 COMPLETE SPECIFICATION (Original) FOR OFFICE USE Class Int. Class Application Number: Lodged: Complete Specification Lodged: Accepted: Published: Priority: 4 Related Art: 4 Name of Applicant: PALM OIL RESEARCH DEVELOPMENT BOARD S Address of Applicant: No.6, Persiaran Institusi, Bandar Baru Bangi, 43000 Kajang, o *Selangor, Malaysia 4 Actual Inventor(s) 001 Cheng Keat, SCHOO Yuen May, ONG Soon Hock Augustine, Address for Service: DAVIES COLLISON, Patent Attorneys, 1 Little Collins Street, Melbourne, 3000.
Complete Specification for the invention entitled: A "RECOVERY OF CAROTENOIDS" The following statement is a full description of this invention, including the best method of performing it known to us: -1 Ui -2-
II
i RECOVERY OF CAROTENOIDS This invention relates to a process for producing carotenoid concentrates and has particular but not exclusive application to a process for recovering carotenes from palm oil, palm oil products or other carotene-containing oils or solutions.
Carotenoids are the principal oil soluble yellow to orange red pigments found in plants and animals.
i Generally, there are two classes of carotenoids, that is Sthe carotenes and xanthophylls. Carotenes are hydrocarbon carotenoids while xanthophylls are oxygenated carotenoids.
Carotenoids are highly unsaturated compounds and are easily decomposed by heat, light and oxygen.
The more widely known carotenes are the alpha-, beta- and gamma-carotenes and lycopene. Some of the -3carotenes are precursors of vitamin A. Beta-carotene is a precusor of vitamin A and has also been shown to inhibit tumour progression, hence to reduce cancer formation. As the carotenes are natural compounds and in view of their vitamin A property, they are widely used in commercial applications in pharmaceutical and nutritional products The most important sources of carotenes are from vegetables, fruits and vegetable oil such as red palm oil.
Among these sources, palm oil is the richest source of carotenes. The orange red colour of palm oil is due to the presence of the carotenes. The concentration of carotenes j c' in palm oil can range from' 500 ppm to 3000 ppm, depending on the species of the palm fruit from which the oil is obtained. The commercial red palm oil contains about 15 500-700 ppm of carotenes, of which alpha-and beta- Scarotene form up to 90% of the total carotenes. So far, commercial production of natural carotenes has mainly i relied upon carrots as a source, while commercial extraction of carotenes from palm oil has to date not been very successful.
Some of the common techniques used in the recovery of carotenes from palm oil are saponification followed by i: extraction, the adsorbent method, extraction by selective 1i 25 solvents, crystallisation and molecular distillation of ji carotenes from the oil. With most of these techniques, large scale production of carotenes from palm oil would be very expensive and involve too many steps in the process.
The present invention accordingly provides a simple process for the recovery of carotenes from palm oil, palm oil products or other carotene-containing oils or solutions, comprising mixing edible oil with esterified -4carotene-containing oil or solution containing carotenes and subjecting the resulting mixture to a pressure of less than 0.060 Torr and a temperature of less than 200 0
C,
without incurring substantial decomposition of the carotenes during the process.
The temperature is preferably in the range 50 to 200 0 C, more preferably 70 to 190 0 C. The pressure is preferably in the range 0.002 to 0.060 Torr. The percentage of edible oil added to the esterified oil containing carotenes or the other solution containing carotenes is preferably in the range 0.1% to 50%, more preferably 1% to 10%, parts by weight of the mixture.
Jt According to one preferred embodiment of the invention, the esterified oil containing carotenes or the other solution containing carotenes is mixed with 0.1% to 50% parts by weight of an edible oil and the resulting S° mixture is passed through a distillation apparatus, preferably at a temperature range of 50 to 200°C and a o 00 pressure range 0.002 to 0.060 Torr.
The esterified oil containing carotenes or the other solution containing carotenes can be the alkyl esters such as the methyl esters, ethyl esters, isopropyl esters or butyl esters of the fatty acids of palm oil and its products, or any other food grade solvents that made up the solution. The edible oil used is preferably palm oil and its products, such as palm olein, palm stearin, neutralized palm oil, neutralized palm olein, or other vegetable oils. In this process, the alkyl esters of the fatty acids of palm oil or its products, or the other food grade solvents of the solution containing the carotenes, in the mixture are distilled off, while the carotenes are concentrated in the edible oil fraction. The carotenes concentrate is dark red in colour. The carotenes in the concentrates or edible oil are substantially stable over a long period of time and have a concentration of at least 1000 ppm and above. The concentration of the carotenes can i 5 range from 1000 ppm to 30000 ppm or higher depending on the concentration of the starting material or proportion of edible oil that is added to the esterified oil containing carotenes or solution containing carotenes.
Preferably, the mixture is heated to the required temperature and then allowed to pass through a S distillation apparatus where the temperature of the i "mixture is maintained and the required pressure created.
SThe distilled alkyl esters or food grade solvents are collected in a separate container from the carotene concentrate.
Preferably the esterified oil or esterified palm oil containing the carotenes are prepared via esterification or transesterification of palm oil or oils containing carotenes. If a solution containing carotene is employed to form the mixture, it may be esterified also if inecessary or desirable. The oil used in the esterification or transesterification is preferably palm oil, palm olein, or palm stearin or any other vegetable oil containing carotenes. The alkyl esters produced by the esterification or transesterification process are preferably the methyl, ethyl, isopropyl or butyl esters of the fatty acids. The edible oil added to the esterified oil containing carotenes or solution containing carotenes is preferably palm oil and palm oil products such as palm olein and palm stearin, other vegetable oils such as peanut, soyabean, corn, rapeseed, sunflower, olive,
-I
-6palmkernel, coconut and fish oils, in each case, either crude, degummed and bleached, refined bleached and deodorised or refined.
The present invention will now be illustrated by the following examples.
Example 1 200 parts by weight of crude palm oil having a concentration of 645 ppm and free fatty acids of less than 5% was transesterified with 79 to 120 parts by weight of methanol and 0.5 to 1.0 parts by weight of a base catalyst. After the transesterification reaction, the ester was separated from the glycerol, and washed with water until the washing was neutral. The ester was then dried using drying agents or vacuum. The dried ester was still orange red in colour and has a carotene content of 700 ppm.
20 200 parts by weight of dried ester was then added with 20 parts by weight of refined and deodorised (RD) red palm oil. The resulting mixture was then passed through a vacuum distillation column(molecular distillator) at a pressure of 0.020 to 0.025 Torr and a temperature of 90 0
C.
The concentration of carotene of the concentrate obtained after the distillation was 6570 ppm.
The experiment was repeated using different temperatures for distillation and the results are shown in Table 1.
-7- TABLE 1 Temperature (oC) 110 130 150 170 Carotene Concentrate (ppm) 6650 6687 6754 6985 Example 2 200 parts by weight of the dried ester as prepared in Example 1 was added with 10 parts by weight of refined and deodorised (RD) red palm oil. The resulting mixture was then passed through a vacuum distillation column(molecular distillator) at a pressure of 0.020 to 10 0.025 Torr and a temperature of 90 0 C. The concentration of carotene of the concentrate obtained after the distillation was 9673 ppm.
The experiment was repeated using different temperatures for distillation and the results are shown in Table 2.
t t TABLE 2 Temperature (oC) 110 130 150 170 Carotene Concentrate (ppm) 9754 9799 9861 9980 Example 3 200 parts by weight of the dried ester as prepared in Example 1 was added with 5 parts by weight of refined and deodorised (RD) red palm oil. The resulting mixture was then passed through a vacuum distillation column(molecular distillator) at a pressure of 0.020 to 0.025 Torr and a temperature of 90 0 C. The concentration of carotene of the concentrate obtained after the distillation was 18762 ppm.
The experiment was repeated using different temperatures for distillation and the results are shown in Table 3.
TABLE 3 Temperature 110 130 150 170 Carotene Concentrate (ppm) 18798 18861 18890 18994 Example 4 200 parts by weight of crude palm oil having a concentration of 645 ppm and free fatty acids of less than was transesterified with 79 to 135 parts by weight of ethanol and 0.5 to 1.0 parts by weight of a base catalyst.
After the transesterification reaction, the ester was separated from the glycerol, and washed with water until the washing was neutral. The ester was then dried using drying agents or vacuum. The dried ester was still orange red in colour and has a carotene content of 705 ppm.
SII
200 parts by weight of dried ester was then added with 20 parts by weight of refined and deodorised (RD) red palm oil. The resulting mixture was then passed through a vacuum distillation column(molecular distillator) at a pressure of 0.020 to 0.025 Torr and a temperature of 90 0
C.
VThe concentration of carotene of the concentrate obtained ii h- after the distillation was 6508 ppm.
The experiment was repeated using different temperatures for distillation and the results are shown in Table 4.
TABLE 4 Temperature 110 130 150 170 Carotene Concentrate (ppm) 6597 6637 6761 6887 -9- SExample 200 parts by weigh of the dried ester as prepared in Example 4 was added with 10 parts by weight of refined and deodorised (RD) red palm oil. The resulting mixture was then passed through a vacuum distillation column(molecular distillator) at a pressure of 0.020 to 0.025 Torr and a temperature of 90 0 C. The concentration of carotene of the concentrate obtained after the distillation was 9558 ppm.
The experiment was repeated using different temperatures for distillation and the results are shown in Table TABLE i 15 Temperature (OC) 110 130 150 170 Carotene Concentrate (ppm) 9617 9695 9782 9901 Example 6 200 parts by weight of the dried ester as prepared S in Example 4 was added with 5 parts by weight of refined j and deodorised (RD) red palm oil. The resulting mixture was then passed through a vacuum distillation column(molecular distillator) at a pressure of 0.020 to 0.025 Torr and a temperature of 90 0 C. The concentration of 2i carotene of the concentrate obtained after the distillation was 18409 ppm.
The experiment was repeated using different temperatures for distillation and the results are shown in Table 6.
M 1 1 TABLE 6 Temperature (oC) 110 130 150 170 Carotene Concentrate (ppm) 18515 18590 18695 18741 Example 7 S200 parts by weight of the dried ester as prepared in Example 4 was added with 5 parts by weight of refined and deodorised (RD) red palm oil. The resulting mixture was then passed through a vacuum distillation S column(molecular distillator) at a pressure of 0.002 to 10 0.004 Torr and a temperature of 150 0 C. The concentration of carotene of the concentrate obtained after the i distillation was 20783 ppm.
Example 8 S200 parts by weight of the dried ester as prepared in Example 4 was added with 5 parts by weight of refined bleached and deodorised(RBD) palm olein. The resulting mixture was then passed through a vacuum distillation Scolumn(molecular distillator) at a pressure of 0.020 to i 0.025 Torr and a temperature of 130 0 C. The concentration of carotene of the concentrate obtained after the distillation was 18571 ppm.
Example 9 200 parts by weight of the dried ester as prepared in Example 4 was added with 5 parts by weight of neutralised, bleached and degummed (NBD) palm oil. The resulting mixture was then passed through a vacuum distillation column (molecular distillator) at a pressure of 0.020 to 0.025 Torr and a temperature of 90 0 C. The -11concentration of carotene of the concentrate obtained after the distillation was 19048 ppm.
Example 200 parts by weight of the dried ester as prepared in Example 4 was added with 5 parts by weight of refined bleached and deodorised (RBD) palm oil. The resulting mixture was then passed through a vacuum distillation column (molecular distillator) at a pressure of 0.020 to 0.025 Torr and a temperature of 130 0 C. The concentration S of carotene of the concentrate obtained after the S distillation was 18650 ppm'.
Example 11 200 parts t weight of the dried ester as prepared in Example 4 was added with 5 parts by weight of refined and deodorised (RD) red palm olein. The resulting mixture was then passed through a vacuum distillation column (molecular distillator) at a pressure of 0.020 to 0.025 Torr and a temperature of 130°C. The concentration of carotene of the concentrate obtained after the distillation was 19708 ppm.
Claims (19)
1. A process for the recovery of carotenes from palm oil, palm oil products or other carotene-containing oils or solutions, comprising mixing edible oil with esterified carotene-containing oil or solution containing carotenes and subjecting the resulting mixture to a pressure of less than 0.060 Torr and a temperature of less than 200 0 C. S
2. A process as claimed in Claim 1 further including S. transesterification of the carotene-containing oil to I, produce said esterified carotene-containing oil.
3. A process as claimed in Claim 2, wherein the carotene-containing oil used in the transesterification process is crude palm oil. S'
4. A process as claimed in Claim 2, wherein the oil used in the transesterification process is crude palm Solein.
A process as claimed in Claim 2, wherein the carotene-containing oil used in the transesterification process is crude palm stearin. t t
6. A process as claimed in Claim 2, wherein the carotene-containing oil used in the transesterification process is neutralised palm oil.
7. A process as claimed in Claim 2, wherein the carotene-containing oil used in the transesterification process is neutralised palm olein. -13-
8. A process as claimed in any one of Claims 1 to 7, Swherein the esterified oil comprises the methyl esters of the fatty acids originally present in the.oil.
9. A process as claimed in any one of Claims 1 to 7, wherein the esterified oil comprises the ethyl esters of the fatty acids originally present in the oil.
A process as claimed in any one of Claims 1 to 7, wherein the esterified oil comprises the isopropyl esters j of the fatty acids originally present in the oil.
11. A process as claimed in Claim 1, wherein the solution containing carotenes comprises a food grade solvent or a mixture of food grade solvents.
12. A process as claimed in any one of Claims 1 to 11, wherein the edible oil added to the esterified carotene-containing oil or solution containing carotenes is selected from: crude palm oil; Srefined and deodorised (RD) red palm oil; refined, bleached and deodorised (RBD) palm oil; neutralised, bleached and degummed (NBD) palm oil; crude palm olein; neutralised, bleached and degummed(NBD) palm olein; refined, bleached and deodorised(RBD) palm olein; refined and deodorised (RD) red palm olein; neutralised palm oil; neutralised palm olein; bleached and deodorised palm stearin; -14- and mixtures of two or more of said edible oils.
13. A process as claimed in any one of Claims 1 to 11, wherein the edible oil added to the esteri-fied oil or solution containing carotenes is selected from soyabean oil, corn oil, rapeseed oil, sunflower oil, olive oil, peanut oil, palmkernel oil, coconut oil, fish oil, carrot oil, or mixtures of two or more of said oils. sal
14. A proces& as claimed in any one of the preceding claims, wherein the amount of edible oil added to the transesterified oil containing carotenes or solution containing carotenes is in the range of 0.1% to 50% by weight of the resulting mixture.
A process as claimed in any one of the preceding claims, wherein the amount of edible oil added to the transesterified oil containing carotenes or solution 0, containing carotenes is in the range of 1% to 10% by weight of the resulting mixture.
16. A process as claimed in any one of the preceding claims, wherein the process of distillation of the O" resulting mixture is carried out at a temperature in the range 50 to 200 0 C.
17. A process as claimed in Claim 16 wherein the process of distillation of the resulting mixture is carried out at a temperature in the range 70 to 190 0 C.
18. A process as claimed in any one of the preceding claims, wherein the distillation of the resulting mixture is carried out at a pressure in the range 0.002 to 0.060 Torr. ore o te-
19. A process as claimed in any~preceding claim further including passing the mixture through a distillation apparatus where it is subjected to said temperature and pressure. A process for the recovery of carotenes, substantially as hereinbefore described in any of the Examples. a F n r0a Ia rr UT IS=l 1I referred to or indicated in the specific nd/or claims of this applicatio i'dually or collectively, and any and, inations of any two or more of said T-q: -r' I t 4 t 4 44 S.144 DATED this 14th day of June, 1989. DAVIES COLLISON, Patent Attorneys for PALM OIL RESEARCH AND DEVELOPMENT BOARD '444 IV I 'E? r1V O'
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU36320/89A AU634476B2 (en) | 1988-06-14 | 1989-06-14 | Recovery of carotenoids |
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AUPI8768 | 1988-06-14 | ||
AUPI876888 | 1988-06-14 | ||
AUPI8770 | 1988-06-15 | ||
AUPI877088 | 1988-06-15 | ||
AU36320/89A AU634476B2 (en) | 1988-06-14 | 1989-06-14 | Recovery of carotenoids |
Publications (2)
Publication Number | Publication Date |
---|---|
AU3632089A AU3632089A (en) | 1989-12-21 |
AU634476B2 true AU634476B2 (en) | 1993-02-25 |
Family
ID=27153735
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU36320/89A Expired AU634476B2 (en) | 1988-06-14 | 1989-06-14 | Recovery of carotenoids |
Country Status (1)
Country | Link |
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AU (1) | AU634476B2 (en) |
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1989
- 1989-06-14 AU AU36320/89A patent/AU634476B2/en not_active Expired
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AU3632089A (en) | 1989-12-21 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PC | Assignment registered |
Owner name: MALAYSIAN PALM OIL BOARD Free format text: FORMER OWNER WAS: PALM OIL RESEARCH AND DEVELOPMENT BOARD |