GB2218989A - Recovery of carotenoids, tocopherols, tocotrienols and sterols from esterified palm oil - Google Patents
Recovery of carotenoids, tocopherols, tocotrienols and sterols from esterified palm oil Download PDFInfo
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- GB2218989A GB2218989A GB8829427A GB8829427A GB2218989A GB 2218989 A GB2218989 A GB 2218989A GB 8829427 A GB8829427 A GB 8829427A GB 8829427 A GB8829427 A GB 8829427A GB 2218989 A GB2218989 A GB 2218989A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
- C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
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- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
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Abstract
The invention is for a method for the isolation of the minor non-glyceride components of palm oil or like vegetable oil containing free fatty acid and non-glyceride components similar to that of palm oil which method comprises: (i) esterifying the free fatty acid component of the oil with one or more monohydric alcohols to form an esterified oil with every low free fatty acid content, (ii) converting the glycerides into monoesters by transesterification employing one or more monohydric alcohols, (iii) adsorbing the non-glyceride components onto a selective absorbent to separate said components from the esters of the oil, and (iv) thereafter desorbing the non-glyceride components from the adsorbent with the use of solvent to recover said components. The adsorbent is preferably activated alumina, activated carbon, or silica gel, preferably reverse phase (particularly C18) silica gel. By the method, carotenes, sterols, tocopherols and other non-glyceride components can be isolated.
Description
RECOVERY OF CAROTENOIDS, TOCOPHEROLS, TOCOTRIENOLS
AND STEROLS FROM ESTERIFIED PALM OIL
Crude palm oil contains about 1% of non-glyceride components which include carotenoids, tocopherols, tocotrienols and sterols. The carotenoids, consisting of mainly ct and p carotenes at 500 to 700 ppm, are important constituents with pro-vitamin A activity, possible anti-tumor formation properties, and other physiological activities. The tocopherols and tocotrienols are Vitamin E constituents and also natural anti-oxidants, and are present at approximately 600 to 1000 ppm in crude palm oil; the major component is the gamma-tocotrienol which has recently been found to have anti-cancer properties besides its known anti-oxidant activity.Tocotrienol has been found to lower blood cholesterol. (The sterols consists mainly of sitosterols, stigmasterol and campesterol provide raw materials for steroid intermediates 3and drugs).
Several methods have been developed to extract these valuable compounds; In the case of the carotenoids, the known methods can be classified as follows:
(i) Extraction by saponification e.g. British
Patent 567,682; U.S. Patent 2,460,796; U.S. Patent 2,440,029; U.S. Patent 2,572,467; U.S. Patent 2,652,433
(ii) Iodine method
(iii) Urea process
(iv) Extraction using Fuller's earth or activated carbon, eig. British Patent 691,924; British Patent 1,563,794; U.S. Patent 2,484,040
(v) Extraction by selective solvents e.g.
U.S. Patent 2,432,021
(vi) Molecular Distillation.
In the saponific@tion method e t.e oil is saponified to give soap, glycerol and a non-sapcnifiable fraction containing carotenes.
In the iodine method (ii), the-iodinc is added
to a solution of palm oil in petroleum ether, an
insoluble precipitate of carotene di-iodide is formed. The iodo- compound when treated with sodium thiosulphate however yields iso-carotene or debydro-caroten which has no. biological activity.
with the urea- method (iii), the triglycerides are broken down to fatty acids and methyl Esters which then form insoluble compounds with urea and thiourca, leaving the carotenoids in the remaining
liquid.
Extraction of carotenes using adsorbents has been carried out using Fuller's earth and activated carbon (method iv). However, the extraction of the carotenes from the earth gives oxidised or isomerised products of carotenes. Carotene is concentrated six
times in the extract.
Extraction of carotenes by selective solvents
(method v) has been carried out using propane or furùral. The carotene is concentrated (three times that of the original oil). in the furfural phase.
By method (vi) carotenes can also be obtained by molecular distilration (10-3 - 10-4 mm Hg).
Fractions collected at 230 C have a carotene content of about five times that of the original oil.
None of these methods however have been commercialised because of several difficulties.
According to the present invention there is a method for the isolation of the minor non-glyceride components of palm oil or like vegetable oil containing free fatty acid and non-glyceride components similar to that of plam oil, which method comprises:
(i)' Esterifying the free fatty acid component c' the oil with one or more monohydric alchols to form an esterified oil with a very low free fatty.
acrid content,
(ii) converting the glycerides into monoesters by transesterification employing one or more monohydric alcohols,
(iii) adsorbing the non-glyceride components onto a selective adsorbent to separate said components from the esters of the oil, and
(iv) thereafter desorbing the non-glyceride components from the adsorbent with the use of solvent to recover said components.
The present method used a selective adsorbent for the adsorption of the minor.non-glyceride components from esterified palm oil. We have found that this method is pqssible because, unlike crude palm oil, esterified plam oil possesses suitable physical and chemical properties. Passage of the e sterified palm oil with or without solvent through a selective adsorbent allows solid phase extraction or trapping of carotenoids, sterols, tocopherols and tocotrienols.
It is a surprising discovery that solid adsorbents such as alumina or silica gel, or carbon contrary to the expectation of .a.skilled worker in the art, provide a very satisfactory uay of obtaining the minor non-glyceride components which include the carotenes sterols, tocopherois etc. from the original vegetable oils.
In a typical extraction of carotens from pal: esters (e:g. methyl esters) prepared in accordanc with British Patent Specification sa48897A, passage through bonded phase silica gel provides a recovery of 70? of the available carotenes in the form of a concentrate. Extraction is possible in the presence of alcohols (e.@. methanol, ethanol etc.) from which the esters have been prepared. In t typical extraction of sterols, tocopherols and tocotrienols, palm esters are passed thrcvgh. suitable adsorbents such as activated alumina and silica gel. where they are selectively adsorbed and later desorbed using suitable solvents.Purification to pure components can be carried out using conventional chromatographic techniques.
The present method alloys for the recovery from palm oil of several valuable minor components. the value of which can surpass that of the oil. The industrial preparation of palm esters for oleochemicals, detergents, palm diesel, etc. opens sup an important avenue for the recovery of'these minor - components.
Follouing is a description by way of example'of the recovery of carotonoids, tocopherols, tocotrienols and sterols by reverse phase (Cl8) silica gel carbon and alumina adsorbents.
Example 1
Crude palm oil methyl ester was dissolved in methanol (30 ml) and the mixture was introduced into a glass column packed with C18 reverse phase (1Sg) the packing having a height of 20 cm and diameter of 1.8 cm. The ester eluted first and was collected and pumped as fraction W1. More methanol was introdueed into tile column to elute out as much ester as possible until carotenoid was about to be eluted out and this was collected and pumped as fraction
Hexane and methanol (98:2 v/v) or chloroform was used to elute out the carotenoid and this was collected as fractrion W3. Occasionally the column was then cleaned up once with chloroform (40 ml) giving rise to fraction W4. The column was then soaked in methanol for further use.A chromatographic separation was carried out under a nitrogen atmosphere and the recovery of carotenes was determined at 446 nm. The results are shown in
Table 1.
Table 1 Recovery of Carotenoids from Methyl Esters of Neutralis
Palm oil using C18 Reverse Phase as Adsorbent (I)** Recovery of
Methyl Solvents used as Collected Fractions/g Carotenoids
Esters/g Eluent*/ml
A B C D W1 W2 W3 W4 /% 15.19 30 30 15# 40 8.01 4.76 1.76 0.66 66@ 15.02 30 45 55# 15 7.98 4.79 1.86 0.0098 90 15.02 30 30 55# 50## 0.49 5.34 1.17 0.0079 63.9 15.01 30 45 45 40 0.42 5.62 0.94 0.0022 95 15.02 30 45 45 40 0.75 11.62 2.36 0.0034 95
8.01 30 190 45 40 1.79 6.08 0.07 0.0597 81 * Consecutive solventg used as eluent were; A = MeOH (use for dissolving ME);
B = MeOH; C = n-hexane : MeOH (98:2 v/v); D = CHCl3.
** Weight of adsorbent = 15 g.
# Solvent used was chloroform.
## Solvent used was ethanol (95%).
@ This value is based on the 3rd and 4th fractions.
Example 2
The procedure of Example 1 was repeated except
that different amounts of starting materials were
used, ie. methyl esters had first been eluted and cleaned .up.by passing through an alumina column. The
results are shown in Table 2.
Example 3
The procedure of Example 1 was repeated except
that instead of methanol, ethanol was used as eluent and.with different amounts of starting materials. The results are shown in Tabled 3.
Example 4
Recovery of carotenoids, tocopherols,
tocotrienols., and sterols from transesterified NPO
was carried out by adsorption onto C18 reverse
phase.SiO2 followed by alumina.
Neutralised palm oil methyl ester (15g), which
was cleaned by passing though Kieselguhr (70-230 Mesh
ASTM), was dissolved-in methanol (30 ml) and the
mixture was introduced into the glass column packed
with C18 reverse phase ClS g, 20 cm height1 1.8 cm
diameter). The eluted ester was. collected as
fraction 1 (9.20 g).Another 4Sml of-methanol were
intioduced into the column to elute out as much ester
as possible until carotenoids were about to be eluted
out and these were collected as fractions 2 and 3
(3.67 g and 1.91 g respectively). 45 ml of hexane
and methanol (98:2 v/v) were used to elute out the Table 2 Recovery of Carotenoids from Methyl Esters of Neutralis
Palm oil using C18 Reverse Phase as Adsorbent (I)** Recovery of
Methyl Solvents used as Collected Fractions/g Carotenoids
Esters/g Eluent*/ml
A B C D W1 W2 W3 W4 /% 15.00 30 30 15# 15 8.30 5.04 1.56 0.0409 74.7
3.76 30 30 45 30 0.17 2.44 1.03 0.1039 80.6
2.10 30 30 45 30 0.05 1.79 0.23 0.0303 39.2
2.01 30 30 45 30 - 1.90 0.13 0.0150 26
1.04 30 30 45 30 0.01 0.91 0.11 0.0144 4 * Consecutive solventg used as eluent were;A = MeOH (use for dissolving ME);
B = MeOH; C = n-hexane : MeOH (98:2 v/v); D = CHCl3.
** Weight of adsorbent = 15 g.
# Solvent used was chloroform.
## Solvent used was ethanol (95%).
@ These methyl esters samples had first been eluted through an alumina Table 3 Recovery of Carotenoids from Methyl Esters of Neutralis
Palm oil using C18 Reverse Phase as Adsorbent (I)** Recovery of
Methyl Solvents used as Collected Fractions/g Carotenoids
Esters/g Eluent*/ml
A B C D W1 W2 W3 W4 /% 15.02 30 55 55# - 0.17 14.75 - - all@
8.01 30 60 45 30 0.03 7.59 0.12 - 92.3
6.00 30 100 55 40 3.00 2.80 0.10 0.1003 93.6
3.75 30 30 65 30 0.23 2.76 0.67 0.0381 87 * Consecutive solventg used as eluent were; A = 95% EtOH (use for dissolving
ME); B = 95% EtoH; C = n-hexane : EtOH (98:2 v/v); D = CHCl3.
** Weight of adsorbent = 15 g.
# Solvent used was chloroform.
@All carotenoids had been eluted out together with methyl esters in fraction
W2.
carotenoids and this was collected as fraction 4 (0.1785 g). Chromatography separtion was carried out under a nitrogen atmosphere. The percentage recoveries of carotenoids (quantified by uvivlcible spectrophotometry) , tocopherols and tocotrienols (quantified by GLC) of cach of the four fractions above ire tabulated in Table 4.
Fractions 1, t and 3 (tctal 12.84 g) in which most of the tocopherols, tocotrienols and sterols were found were then combined and eluted into a glass column packed with neutral alumina (1.43 g; ratio of methyl ester:adsorbent, 9:1 w/w). The height of the packing material was 4.5 cm and the diameter of the column was 0.8 cm. The methyl ester eluted was collected as fraction 1 (11.75g). n-Hexane (2 x 12.9m1) was introduced into the column to clean up as much methyl cster as possible and this was collected as fraction 2 (0.9 g). Finally, chloroform (4 z 8.6 m})-was used to recover the sterols, tocopherols 'and tocotrienols from alumina and this was collected as fraction~3.Chromatogfaphy separation was carried out under nitrogen atmosphere. Percentage recoveries of tocopherols and tocotrienols, and sterols in each of the above three fractions were worked out and the results are shown in Table 5.
.Example5 -. The recovery of carotenoids, tocopherols and tocotrienols, and sterols was performed by adsorption onto alumina followed by C18 reverse phase silica
Gel.
Neutralised palm oil methyl esters (90 g) was cleaned up by filtering through Xieselguhr and then eluted into a glass column packed with alumina (neutral, 10 g, 3.5 cm height and 2.5 cm diameter).
The eluted methyl esters were collected as fraction 1
Table 4 Recovery of Carotenoids, Tocopherols and
Tocotrienols, and Sterols from Methyl Esters of Neutralised
Palm oil using C18 Reverse Phase Silica Gel ------------------------------------------------
Fraction Recovery*/%
Carotenoids Tocopherols and Sterols
Tocotrienols
1 5.2 61.7 (556) 9
2 3.5 19.9 (450) - 8.3
3 6.3 11.9 (516) 6.3
4 67.4 2.3 (1045) ND# * Recovery in ppm is bracketed.
# ND = Not Detectable.
Table S Recovery of Tocopherols, Tocotrienols and
Sterols from Methyl Esters of Neutralised Palm Oil using
Alumina as Adsorbent (I)* -- Fraction Recovery@/% Tocopherols & Tocotrienols Sterols --------------------------------------------------
1 79.4 (366) 30.1
2 5.8 (347) 18.9
3 2.6 (1510) 15.4 * The methyl esters used has first been eluted through the
C18 reverse phase column to remove carotenoids as shown in
Table 4 I Recovery in ppm is bracketed.
(82.23 g). n-Hexane (210 ml) was then introduced
into the column to clean up as much methyl esters as
possible and this was collected as fraction 2 (6.81 -g).' rinally4chloroform (240 @l) was used to recover
the adsorbed components including tocopherols and
tocotrienols, and sterols from the starting material
used (i.e. neutralised palm oil methyl esters) in the
3 fractions collected is shown in Table 6.
15.3 g of eluted methyl esters from fraction l above was then dissolved in methanol (30 ml) and the
mixture was introduced into the glass column packed
with C18 reverse phase SiO2 (15 g; 20 cm height, cm cm diameter). The ester eluted was collected as
fraction 1 (9.04 g). Another 45 ml of methanol was
introduced into the column to elute out as much ester as possible before the carotenoids were eluted out
and this was collected as fraction 2 (5.83 g).
n-Hexane and methanol (98:2, 45 ml) were used
elute out the carotenoids and collected as fraction 3
(0.32 g). The column was then cleaned up once with chlorcfc@m (40 ml) and then soaked in methanol for
further use. The chromatography was carried out
under nitrogen atmosphere. The percentage recoveries
of carotenoids, tocopherols and tocotrienols, and
sterols of each of the three fractions above were
worked out and tabulated in Table 7.
Table 6 Recovery of Tocopherols, Tocotrienols and
Sterols from Methyl Esters of Neutralised Palm Oil using
Alumina as Adsorbent (II)
Fraction Recovery@/% Tocopherols & Tocotrienols Sterols --------------------------------------------------
1* 77.8 (357) 72.5
2 10.4 (577) 13.2
3 5.7 (3315) 6.8 * A portion of methyl esters eluted was passed through C18 reverse phase to recover carotenoids as shown in Table 7.
ii Recovery in ppm is bracketed.
Table 7 Recovery of Carotenoids, Tocopherols and
Tocotrienols, and Sterols from Methyl Esters of Neutralised
Palm Oil using C18 Reverse Phase as Adsorbent*
Fractio Recovery@/% Carotenoids Tocopherols and Sterols
Tocotrienols
1 1 6.04 71.6 (423) 42.5
2 i,72 -33.;7 -(-316) 12.3
3 89.06 1.7 (290) ND * The methyl esters used has first been eluted through the alumina column as shown in Table 6.
I The percentage recovery was based on the starting materia used in the column. Recovery in ppm is bracketed.
ND = Not Detectable.
It is understood that in place of the methyl alcohol used to produce. the above described methyl esters any of the branched or straight chain alcobol having from I to 6 carbon atoms may be used, although methyl alcohol is preferred.
Table 8 Adsorption and Extraction of Carotenoids of Methyl ESters of Crude Palm Oil using Activated Carbon
Continuous Column Extraction*
Experiment Adsorption of Recovery of
Carotenoids/% Carotenoids/%
1# 79 49
2## 88 50.6
------------------------------------------------- *The following conditions were used:- weight of methyl esters = 5g; weight of carbon = 1 g; ratio of methyl esters to carbon =5:1; weight of butylated hydroxytoluene (BHT) = 0.01 g; adsorption was sone at 28-30 C; percentage recovery of carotenoids from carbon was from toluene fraction only.
# 18 ml of petroleum ether b.p. 60-80 C, 88 ml of toluene and 38 ml of toluene/ethanol (3:1 v/v) successively were used as eluent; all solvents were at 28-3 C.
## 10 ml of n-hexane (of which 5 ml was used to dossp;ve methyl esters), 43 ml of toluene and 17 ml of toluene/ethanol were used as eluent; both toluene and toluene/ethanol were pre-warmed to 400C before use.
Table 9 Adsorption and Extraction of Carotenoids of Methyl Esters of crude
Palm Oil using Activated Carbon - Batchwise Extraction* ------------------------------------------------------------------------------------------------------------------------
Exp. Activated Solvent for Adsorption of Recovery of Remarks
Carbon Recovery/ml Carotenolds/% Carotenoids/% ----------------------------------------------------------------------------------------------------------------------1 Carbon S511 CH2Cl2; 120 25.2 3.8 Untreated carbon;
Carbon pH = 11.8 2 Norit OL CH2Cl2; 120 61.2 3.3 Untreated carbon 3 Carbon S511 CH2Cl2; 120 70.3 3 Carbon was warmed
amd vacuum pumped
dry before use 4 Carbon S511 CH2Cl2; 120 73.5 2.4 Antioxidant hydro
quinone; carbon
was vacuum pumped
dry before use.
5 Carbon S511 CH2Cl2; 120 66.5 10.3 Carbon - treated
with EtoH, HCl & BR<
Na2CO3; activated
at 300 C; pumped
dry at 200 C; pll
=10.1 6# Carbon S511 Toluene; 60 61.9 26.1 Carbon was pumped
at 250 C for 2 hr *The following conditions were used: weight of methyl
Carbon = 4 g; methyl esters : carbon = 5:1; adsorption done at 28-3 C; recovery of carotenoids from carbon
Soxhlet extractor with solvent.
# Recovery of carotenoids from carbon was done by soaking the carbon in toluene.
Claims (13)
1. A method for the isolation of the minor non-glyceride components . of palm oil or like vegetable oil containing free fatty acid and non-glyceride components similar to that of palm oil, which method comprises:
(i) esterifying the free fatty acid component of the oil with one or more monohydric alcohols to form an esterified oil with very low free.fatty acid content,
(ii) converting the glycerides into monoesters by transesterification employing one or more monohydric alcohols,
(iii) adsorbing the non-glyceride components onto a selective a#scrbent to separate said components from the esters of the oil, and
(iv) thereafter desorbing the non-glycerlde components from the adsorbent with the use of solvent to recover said components.
2. A method as claimed in claim 1 wherein the adsorbent is activated alumina carbon or silica gl, preferably reverse phase (particularly C 18) silica gel.
3. A method as claimed in claim 1 or claims 2 wherein the non-giyceride components obtained from step (iii) are separated into sterols, tocopheroLs, tocotrienols and carotenes by a chromatographic technique, cr wherein the reo@@vered minor o@mp##ent is cnly carctene by using carbon adsorbent.
4. A method as claimed in any one of the preceding claims wherein the esterification of step (i) is carried out employing (a) a solid alkali metal bisulphate or (b) a sulphate acid strongly-acidic ion-exchange resin as a catalyst and the transesterification of step (ii) is carried out employing a basic catalyst or both the esterification and transesterification are carried out using an enzyme e.g. candida rugosa.
5. A method as claimed in any one of the preceding claims wherein the oil which is esterified in step (i) is a palm oil or a palm oil fraction.
6. A method as claimed in any one of the preceding claims wherein the carboxylic acid is esterified and/or the glycerides are transesterified with one or more C1 to C3 alcohols, preferably methanol.
7; A method as claimed in any one of claims 4 to 6 wherein there is employed from 1 to 20% by weight of catalyst, based upon the weight of the free fatty carboxylic acid.
8; A method for the recovery of- carotenes from esterified palm oil by employing a C 18 reverse phase silica gel as adsorbent using two combinations of solvents as consecutive eluents as follows
(i) Methanol, n-hexane : ethanol (98 : 2 v/v) and CHCl3
(ii) Ethanol, n-hexane : 95% EtOH (98 : 2 v/v) and CHCl3.
9. A method as claimed in claim 9 in which the recovery of carotenes from esterified palm oil is at least 95S with a ratio of methyl ester to adsorbent of 1 : 1 (w/w) on the recovery of carotenes from esterfied palm oil is at least 92.3$ when the ratio of methyl esters to adsorbent is o.5 : 1 (w/w).
10. A method for the recovery of carotenes from esterified plam oil by employing activated carbon as adsorbent and using aromatic solvent such as toluene or aliphatic solvent such as dichioromethane or ethanol for desorbing carotene s from the carbon.
11. A method for the isolation of the minor non-glyceride components of palm oil or the like substantially as hereinbefore described in .any one of the examples.
12. A non-glyceride component of palm oil or the like when obtained using a process as claimed in any one of claims I to 11.
13. Sterols, tocopherols, tocotrienols and carotenes when obtained from the component of clatm 12.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB878729232A GB8729232D0 (en) | 1987-12-15 | 1987-12-15 | Recovery of carotenoids tocopherols tocotrienols & sterols from esterified palm oil |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8829427D0 GB8829427D0 (en) | 1989-02-01 |
| GB2218989A true GB2218989A (en) | 1989-11-29 |
| GB2218989B GB2218989B (en) | 1991-09-04 |
Family
ID=10628516
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB878729232A Pending GB8729232D0 (en) | 1987-12-15 | 1987-12-15 | Recovery of carotenoids tocopherols tocotrienols & sterols from esterified palm oil |
| GB8829427A Expired - Lifetime GB2218989B (en) | 1987-12-15 | 1988-12-15 | Recovery of carotenoids, tocopherols, tocotrienols and sterols from esterified palm oil |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB878729232A Pending GB8729232D0 (en) | 1987-12-15 | 1987-12-15 | Recovery of carotenoids tocopherols tocotrienols & sterols from esterified palm oil |
Country Status (2)
| Country | Link |
|---|---|
| GB (2) | GB8729232D0 (en) |
| MY (1) | MY104388A (en) |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0421419A2 (en) * | 1989-10-04 | 1991-04-10 | Bristol-Myers Squibb Company | Tocotrienols in the treatment of hypercholesterolemia, hyperlipidemia and thromboembolic disorders |
| US5157132A (en) * | 1990-05-18 | 1992-10-20 | Carotech Associates | Integrated process for recovery of carotenoids and tocotrienols from oil |
| US5217992A (en) * | 1989-10-04 | 1993-06-08 | Bristol-Myers Squibb Company | Tocotrienols in the treatment of hypercholesterolemia, hyperlipidemia and thromboembolic disorders |
| WO1994005650A1 (en) * | 1992-08-27 | 1994-03-17 | Henkel Kommanditgesellschaft Auf Aktien | Isolation of tocopherol and sterol |
| US5670668A (en) * | 1996-07-03 | 1997-09-23 | Eastman Chemical Company | Crystalline tocotrienol esters |
| US5902890A (en) * | 1995-03-20 | 1999-05-11 | Henkel Kommanditgesellschaft Auf Aktien | Process for obtaining carotene from palm oil |
| US6072092A (en) * | 1994-03-18 | 2000-06-06 | Palm Oil Research & Development Board | Recovery of carotenes |
| EP1097985A1 (en) * | 1999-11-04 | 2001-05-09 | Malaysian Palm Oil Board | A Method of chromatographic isolation for non-glyceride components |
| EP1122250A1 (en) * | 2000-02-02 | 2001-08-08 | Malaysian Palm Oil Board | A method of chromotagraphic isolation for vitamin E isomers |
| GB2371545B (en) * | 2000-12-14 | 2003-07-02 | Supervitamins Sdn Bhd | Recovery of minor components and refining of vegetable oils and fats |
| GB2387384A (en) * | 2000-12-14 | 2003-10-15 | Supervitamins Sdn Bhd | Recovery of minor components from vegetable oils and fats |
| EP1424013A1 (en) * | 2002-11-27 | 2004-06-02 | Malaysian Palm Oil Board | A method of extracting and isolating minor components from vegetable oil |
| WO2005051294A2 (en) | 2003-11-19 | 2005-06-09 | Carotech Inc. | Recovery of phytonutrients from oils |
| US7173145B2 (en) | 2001-11-29 | 2007-02-06 | University Of Maryland, College Park | Process for extraction and purification of lutein, zeaxanthin and rare carotenoids from marigold flowers and plants |
| US7507847B2 (en) | 2005-02-17 | 2009-03-24 | Palm Nutraceuticals Sdn. Bnd. | Quality of crude oils and fats and recovery of minor components |
| WO2009105351A1 (en) * | 2008-02-21 | 2009-08-27 | Dow Global Technologies Inc. | Separation of natural oil-derived aldehydes or hydroxy methyl esters using process chromatography |
| US8003144B2 (en) | 2004-09-01 | 2011-08-23 | Malaysian Palm Oil Board | Specialty palm oil products and other specialty vegetable oil products |
| CN103627519A (en) * | 2012-08-29 | 2014-03-12 | 丰益(上海)生物技术研发中心有限公司 | Method for removing total cholesterol in animal fat |
| WO2014129974A1 (en) * | 2013-02-22 | 2014-08-28 | Shayonano Singapore Pte Ltd | Process for the isolation of carotenoids |
| US11154795B2 (en) | 2016-10-21 | 2021-10-26 | Novasep Equipment Solutions | Use of compressed gas for moving eluent applied to chromatography |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1562794A (en) * | 1976-11-26 | 1980-03-19 | Univ Sains Malaysia | Method for the extraction of carotenes from palm oil |
| GB2090836A (en) * | 1980-12-15 | 1982-07-21 | Agency Ind Science Techn | Method for the preparation of tocotrienol concentrates from oleaginous materials |
| GB2148897A (en) * | 1983-11-03 | 1985-06-05 | Inst Penyelidikan Minyak Kelap | Catalytic esterification of carboxylic acid/glyceride mixtures |
-
1987
- 1987-12-15 GB GB878729232A patent/GB8729232D0/en active Pending
-
1988
- 1988-12-15 GB GB8829427A patent/GB2218989B/en not_active Expired - Lifetime
-
1989
- 1989-01-04 MY MYPI89000007A patent/MY104388A/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1562794A (en) * | 1976-11-26 | 1980-03-19 | Univ Sains Malaysia | Method for the extraction of carotenes from palm oil |
| GB2090836A (en) * | 1980-12-15 | 1982-07-21 | Agency Ind Science Techn | Method for the preparation of tocotrienol concentrates from oleaginous materials |
| GB2148897A (en) * | 1983-11-03 | 1985-06-05 | Inst Penyelidikan Minyak Kelap | Catalytic esterification of carboxylic acid/glyceride mixtures |
Cited By (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0421419A2 (en) * | 1989-10-04 | 1991-04-10 | Bristol-Myers Squibb Company | Tocotrienols in the treatment of hypercholesterolemia, hyperlipidemia and thromboembolic disorders |
| EP0421419A3 (en) * | 1989-10-04 | 1992-04-01 | Bristol-Myers Squibb Company | Tocotrienols in the treatment of hypercholesterolemia, hyperlipidemia and thromboembolic disorders |
| US5217992A (en) * | 1989-10-04 | 1993-06-08 | Bristol-Myers Squibb Company | Tocotrienols in the treatment of hypercholesterolemia, hyperlipidemia and thromboembolic disorders |
| US5157132A (en) * | 1990-05-18 | 1992-10-20 | Carotech Associates | Integrated process for recovery of carotenoids and tocotrienols from oil |
| WO1994008987A1 (en) * | 1990-05-18 | 1994-04-28 | Carotech Associates | Integrated process for recovery of carotenoids and tocotrienols from oil |
| WO1994005650A1 (en) * | 1992-08-27 | 1994-03-17 | Henkel Kommanditgesellschaft Auf Aktien | Isolation of tocopherol and sterol |
| US5627289A (en) * | 1992-08-27 | 1997-05-06 | Henkel Kommanditgesellschaft Auf Aktien | Recovery of tocopherol and sterol from tocopherol and sterol containing mixtures of fats and fat derivatives |
| US6072092A (en) * | 1994-03-18 | 2000-06-06 | Palm Oil Research & Development Board | Recovery of carotenes |
| US5902890A (en) * | 1995-03-20 | 1999-05-11 | Henkel Kommanditgesellschaft Auf Aktien | Process for obtaining carotene from palm oil |
| US5670668A (en) * | 1996-07-03 | 1997-09-23 | Eastman Chemical Company | Crystalline tocotrienol esters |
| EP1097985A1 (en) * | 1999-11-04 | 2001-05-09 | Malaysian Palm Oil Board | A Method of chromatographic isolation for non-glyceride components |
| US6586201B1 (en) | 1999-11-04 | 2003-07-01 | Choo Yuen May | Method of chromatographic isolation for non-glyceride components |
| AU781701B2 (en) * | 1999-11-04 | 2005-06-09 | Malaysian Palm Oil Board | A method of chromatographic isolation for non-glyceride components |
| EP1122250A1 (en) * | 2000-02-02 | 2001-08-08 | Malaysian Palm Oil Board | A method of chromotagraphic isolation for vitamin E isomers |
| JP2001261671A (en) * | 2000-02-02 | 2001-09-26 | Malaysian Palm Oil Board | Method of isolating vitamin e isomers by chromatography |
| US6656358B2 (en) | 2000-02-02 | 2003-12-02 | Malaysian Palm Oil Board | Method for the chromatographic isolation of vitamin E isomers |
| JP2012140467A (en) * | 2000-02-02 | 2012-07-26 | Malaysian Palm Oil Board | Method for chromatographic isolation of vitamin e isomer |
| GB2371545B (en) * | 2000-12-14 | 2003-07-02 | Supervitamins Sdn Bhd | Recovery of minor components and refining of vegetable oils and fats |
| GB2387384A (en) * | 2000-12-14 | 2003-10-15 | Supervitamins Sdn Bhd | Recovery of minor components from vegetable oils and fats |
| GB2387384B (en) * | 2000-12-14 | 2003-12-24 | Supervitamins Sdn Bhd | Recovery of minor components and refining of vegetable oils and fats |
| SG114611A1 (en) * | 2000-12-14 | 2005-09-28 | Supervitamins Sdn Bhd | Recovery of minor components and refining of vegetable oils and fats |
| US7173145B2 (en) | 2001-11-29 | 2007-02-06 | University Of Maryland, College Park | Process for extraction and purification of lutein, zeaxanthin and rare carotenoids from marigold flowers and plants |
| EP1424013A1 (en) * | 2002-11-27 | 2004-06-02 | Malaysian Palm Oil Board | A method of extracting and isolating minor components from vegetable oil |
| JP2004175805A (en) * | 2002-11-27 | 2004-06-24 | Malaysian Palm Oil Board | Method for extracting and isolating minor component from vegetable oil |
| US7161055B2 (en) | 2002-11-27 | 2007-01-09 | Malaysian Palm Oil Board | Method of extracting and isolating minor components from vegetable oil |
| JP4642341B2 (en) * | 2002-11-27 | 2011-03-02 | マレーシアン・パーム・オイル・ボード | Method for extracting and isolating minor components from vegetable oils |
| WO2005051294A2 (en) | 2003-11-19 | 2005-06-09 | Carotech Inc. | Recovery of phytonutrients from oils |
| EP1689353A2 (en) * | 2003-11-19 | 2006-08-16 | Carotech Inc. | Recovery of phytonutrients from oils |
| EP1689353B1 (en) * | 2003-11-19 | 2013-01-09 | Carotech Inc. | Recovery of phytonutrients from oils |
| US8003144B2 (en) | 2004-09-01 | 2011-08-23 | Malaysian Palm Oil Board | Specialty palm oil products and other specialty vegetable oil products |
| US7507847B2 (en) | 2005-02-17 | 2009-03-24 | Palm Nutraceuticals Sdn. Bnd. | Quality of crude oils and fats and recovery of minor components |
| WO2009105351A1 (en) * | 2008-02-21 | 2009-08-27 | Dow Global Technologies Inc. | Separation of natural oil-derived aldehydes or hydroxy methyl esters using process chromatography |
| CN103627519A (en) * | 2012-08-29 | 2014-03-12 | 丰益(上海)生物技术研发中心有限公司 | Method for removing total cholesterol in animal fat |
| CN103627519B (en) * | 2012-08-29 | 2016-06-08 | 丰益(上海)生物技术研发中心有限公司 | A kind of de-method except total cholesterol in animal tallow |
| WO2014129974A1 (en) * | 2013-02-22 | 2014-08-28 | Shayonano Singapore Pte Ltd | Process for the isolation of carotenoids |
| CN105026368A (en) * | 2013-02-22 | 2015-11-04 | 莎尤纳诺新加坡私人有限公司 | Process for the isolation of carotenoids |
| US9592499B2 (en) | 2013-02-22 | 2017-03-14 | Shayonano Singapore Pte Ltd | Process for the isolation of carotenoids |
| US11154795B2 (en) | 2016-10-21 | 2021-10-26 | Novasep Equipment Solutions | Use of compressed gas for moving eluent applied to chromatography |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8729232D0 (en) | 1988-01-27 |
| GB2218989B (en) | 1991-09-04 |
| MY104388A (en) | 1994-03-31 |
| GB8829427D0 (en) | 1989-02-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 711H | Case decided by the comptr. ** correction allowed (sect. 117/1977) | ||
| PE20 | Patent expired after termination of 20 years |
Expiry date: 20081214 |