GB2145418A - Method of separating sterols from deodorisation distillates of oils - Google Patents
Method of separating sterols from deodorisation distillates of oils Download PDFInfo
- Publication number
- GB2145418A GB2145418A GB08402452A GB8402452A GB2145418A GB 2145418 A GB2145418 A GB 2145418A GB 08402452 A GB08402452 A GB 08402452A GB 8402452 A GB8402452 A GB 8402452A GB 2145418 A GB2145418 A GB 2145418A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sterols
- oils
- centrifugal
- distillates
- solvent
- 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.)
- Granted
Links
- 229930182558 Sterol Natural products 0.000 title claims abstract description 49
- 150000003432 sterols Chemical class 0.000 title claims abstract description 49
- 235000003702 sterols Nutrition 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title claims abstract description 17
- 239000003921 oil Substances 0.000 title description 24
- 238000001914 filtration Methods 0.000 claims abstract description 16
- 238000004062 sedimentation Methods 0.000 claims abstract description 14
- 238000001640 fractional crystallisation Methods 0.000 claims abstract description 5
- 239000003925 fat Substances 0.000 claims abstract description 4
- 239000010685 fatty oil Substances 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims description 22
- 230000000694 effects Effects 0.000 claims description 5
- -1 aliphatic ketones Chemical class 0.000 claims description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 239000007788 liquid Substances 0.000 description 36
- 235000019198 oils Nutrition 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
- 239000007787 solid Substances 0.000 description 14
- 238000001953 recrystallisation Methods 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 8
- 238000011084 recovery Methods 0.000 description 8
- 238000005406 washing Methods 0.000 description 6
- 238000000926 separation method Methods 0.000 description 5
- 239000006228 supernatant Substances 0.000 description 5
- 238000004332 deodorization Methods 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 229930003799 tocopherol Natural products 0.000 description 4
- 239000011732 tocopherol Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 235000019149 tocopherols Nutrition 0.000 description 3
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 3
- 235000019484 Rapeseed oil Nutrition 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000002385 cottonseed oil Substances 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 238000005199 ultracentrifugation Methods 0.000 description 2
- 241001133760 Acoelorraphe Species 0.000 description 1
- 241000252073 Anguilliformes Species 0.000 description 1
- 241000255789 Bombyx mori Species 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 244000020518 Carthamus tinctorius Species 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 241000238557 Decapoda Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 235000019774 Rice Bran oil Nutrition 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 210000002683 foot Anatomy 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000008165 rice bran oil Substances 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
A method of separating sterols in deodorisation distillates of fats and fatty oils by solvent-fractional crystallisation, which comprises centrifugal sedimentation and centrifugal filtration.
Description
SPECIFICATION
Method of separating sterols from deodorisation distillates of oils
The present invention relates to a method of separating sterols from the deodorisation distillates which are formed as by-products in the deodorisation step of a process for purifying fats and fatty oils (referred to herein as "oils").
In a conventional purification process, oils such as soybean, rape-seed, cotton-seed, safflower, sunflower, rice-bran, corn, coconut, palm and palm kernel oil are treated in a number of steps, one of which is deodorisation. In deodorisation, scum, slag, hotwell oil foots and other by-products (referred to herein as "deodorisation distillates" or merely "distillates") are formed, and which include, for instance, tocopherols, sterols, hydrocarbons, glycerides and/or free fatty acids.
The sterols may comprise from 1 to 35% by weight of the distillates. The sterols are good emulsifiers and stabilisers, and are good moisture-proofing agents for human skin. They are advantageously used as base materials for cosmetics, as raw materials for the synthesis of drugs such as steroid hormones, and as feed additives, e.g. for lobsters, eels and silkworms. The tocopherols may comprise from 0.1 to 20% by weight of the distillates. They may have utility as drugs, foods or anti-oxidants.
It is difficult to separate tocopherol condensates from the deodorisation distillates when sterols are present. It is therefore necessary to fractionate the sterols before the tocopherols can be isolated. Various methods are known, for the commercial-scale separation of sterols. One approach involves the addition of a material such as a dibasic organic acid, a metal chloride or urea. Another approach involves solvent fractional crystallisation.
In solvent fractional crystallisation, sterol crystals may be separated by ultra-centrifugation. However, ultra-centrifugation requires large-scale apparatus, and it is often difficult to treat the separated sterols satisfactorily. Further, it is necessary to use an amount of solvent much greater than, e.g. 15-30 times, the amount of the distillates, owing to the separational characteristics of sterols. The problem then arises that, since the sterols, accompanied by fatty acids, have some degree of solubility in the solvent, sterols remain in the distillates and may precipitate out in, and adversely affect, subsequent operations.
By way of example, methanol may be used as the solvent. The solubility of certain sterols in methanol is about 2%. The greater amount of solvent used, the larger the sterol content in the distillates after separation.
Sterols in the distillates, after separation, may be prevented from precipitation by adding a further solvent such as hexane, toluene or xylene. The fact that a further component is added, however, complicates solvent recovery.
According to the present invention, a method of separating sterols in deodorisation distillates of fats and fatty oils comprises solvent-fractional crystallisation, centrtifugal sedimentation and centrifugal filtration.
The method of the invention allows sterols to be obtained efficiently, while using only low amounts of solvent, and small-scale apparatus. Simple, manual operations only may be involved. The sterols which are obtained have good dehydration characteristics and can be handled easily.
The method of the invention may involve one or more centrifugal sedimentation operations, and one or more centrifugal filtration operations, in any order. One of each of the operations may give sufficient condensation and isolation of sterols. It is often preferred that a series of centrifugal sedimentation is followed by one centrifugal filtration. More than one of each operation can be more effective, e.g. to increase yields of other components of the distillates. The operations may be advantageously accompanied by others such as the washing of solids.
The accompanying drawing is a flow sheet illustrating a sequence of steps which may be conducted within the scope of the present invention.
With particular reference to the drawing, the deodorisation distillate is first mixed with a solvent. The solvent:distillate ratio is preferably from 1:1 to 1:3. Dissolution may be caused by heating. On complete dissolution, the solution is cooled to 10-20 C in order to precipitate primary sterol crystals. The solution is then passed to a sedimentation centrifuge, for centrifugal sedimentation, and the supernatent liquid is then taken off.
The residual liquid is mixed with further solvent. The solvent:liquid ratio may again be from 1:1 to 1:3. The liquid may again be dissolved in the solvent, by heating. On complete dissolution, the solution is gradually cooled to 0-5 C, in order to recrystallise sterols. If the temperature becomes too low, e.g. -5 to -10 C, fatty acids in the distillates may solidify and cause difficulty in subsequent separation.
The recrystallised solution is passed to a centrifugal filter. The solids thus separated are washed with the same solvent as was used in the centrifugal filtration. The washing solvent:solids ratio may be from 2:3 to 1:1. This washing step facilitates the recovery of oily substances.
The supernatantfrom the centrifugal sedimentation and the filtrate from the centrifugal filtration are combined with the wash liquor. Solids may be dissolved by heating. Cooling of the solution to 0-5 C recrystallises residual sterols which are then separated by centrifugal filtration.
If preferred, recrystallisation, at either stage of the illustrated process, may be achieved by hot filtration of the insolubles.
The sedimentation centrifuge as employed is preferably of the basket-type. The centrifugal effect is preferably from 1000 to 1500. The centrifugal filter as employed is also preferably of the basket-type. The centrifugal effect is preferably from 700 to 900. Low centrifugal effects facilitate handling and save labour.
The solvent used in the invention may be selected from the well-used solvents. Examples are C1 4 aliphatic alcohols such as methanol, ethanol, isopropyl alcohol and isobutyl alcohol, aliphatic carboxylic acid esters such as ethyl acetate, and aliphatic ketones such as methyl isobutyl ketone, methyl ethyl ketone and acetone.
Single solvents or solvent mixtures may be used.
The shape of the crystallites of sterols may vary, depending on the solvent used. However, homogeneous separation may be carried out irrespective of the crystal shape.
The following Examples illustrate the present invention.
Example I
The steps in the flow sheet were followed, using methanol as solvent. The compositions of liquids as treated in each unit operation changed as follows.
(A) Primary Precipitation followed by Centrifugal Sedimentation
Deodorization Distillates 38.2 kg
(Rape-seed Oil) (including 10.28 kg of
sterols)
Methyl alcohol 9.93 kg
Original Supernatant Residual
Liquid Liquid Liquid
Methyl alcohol 9.93 kg 7.15 kg 2.78 kg
Oils* 27.92 22.66 5.26
Sterols 10.28 2.06 8.22
Total 48.13 31.87 16.26 * The ingredients other than sterols in the deodorization distillates are herein given the
general term "Oils" (B) Recrystallization (1)followed by Centrifugal Filtration (1)
Methanol used in the recrystallization 29.8 kg
Original Solid
Liquid Filtrate Fraction
Methyl alcohol 32 58 keg 31.42 kg 1.16 kg
Oils 5.26 4.51 0.75
Sterols 8.22 1.70 6.52
Total 46.06 37.63 8.43 (C) Washing
Methanol used as a wash liquid 21.84 kg
Original Solid
Liquid Wash Liquid Fraction
Methyl alcohol 23.0 kg 22.52 kg 0.48 kg
Oils 0.75 0.61 0.14
Sterols 6.52 0.47 6.05
Total 30.27 23.60 6.67 (D) Recrystallization (2) followed by Centrifugal Filtration (2)
Original Solid
Liquid Filtrate Fraction
Methyl alcohol 61.09 kg 60.83 kg 0.26 kg
Oils 27.78 27.64 0.14
Sterols 4.23 0.49 3.74
Total 93.1 88.96 4.14
Adding up the above:
Original Solid
Liquid Filtrate Fraction
Methyl alcohol 61.57 kg 60.83 kg 0.74 kg
Oils 27.92 27.64 0.28
Sterols 10.28 0.49 9.79
Total 99.77 88.96 10.81
% Recovery of sterols 95.2%
% Recovery of oils 99.0%
Example 2
The method as in Example 1 was repeated, with the exception that isopropanol was used instead of methanol.
(A) Primary Precipitation followed by Centrifugal Sedimentation
Deodorization Distillates 40.0 kg
(Soybean oil) (including 8.8 kg of sterols)
Isopropanol 50.9 kg
Original Supernatant Residual
Liquid Liquid Liquid
Isopropanol 50.9 kg 46.2 kg 4.7 kg
Oils 31.2 28.4 2.8
Sterols 8.8 1.3 7.5
Total 90.9 75.9 15.0 (B) Recrystallization (1)followed by Centrifugal Filtration (1)
Isopropanol used in the recrystallization 50.9 kg
Original Supernatant Residual
Liquid Liquid Liquid
Isopropanol 55.6 kg 50.4 kg 0.5 kg
Oils 2.8 2.5 0.3
Sterols 7.5 1.5 6.0
Total 65.9 54.4 6.8 (C) Washing
Isopropanol used as a wash liquid 12.7 kg
Original Solid
Liquid Wash Liquid Fraction
Isopropanol 13.2kg 12.8kg 0.4kg
Oils 0.3 0.25 0.05
Sterols 6.0 0.4 5.6
Total 19.5 13.45 6.05 (D) Recrystallization (2) followed byCentrifugal Filtration (2)
Original Solid
Liquid Filtrate Fraction
Isopropanol 109.4kg 109.1 kg 0.3kg
Oils 31.15 31.05 0.1
Sterols 3.2 0.4 2.8
Total 143.75 140.55 3.1
Adding up the above:
Original Solid
Liquid Filtrate Fraction
Isopropanol 109.8 kg 109.1 kg 0.7 kg
Oils 31.2 31.05 0.15
Sterols 8.8 0.4 8.25
Total 149.8 140.55 9.25
% Recovery of Sterols 95.5%
% Recovery of Oils 99.5%
Example 3
The method as in Example 1 was repeated with the exception that acetone was used instead of methanol.
(A) Primary Precipitation followed by Centrifugal Sedimentation
Deodorization Distillates 45.0 kg
(Cotton-seed oil) (including 7.8 kg of sterols)
Acetone 113.8kg Original Supernatant Residual
Liquid Liquid Liquid
Acetone 113.8 kg 109.7 kg 4.1 kg
Oils 37.2 36.2 1.0
Sterols 7.8 2.6 5.2
Total 158.8 148.6 10.3 (B) Recrystallization (1) followed by Centrifugal Filtration (1)
Acetone used in the recrystallization 26.0 kg
Original Supernatant Residual
Liquid Liquid Liquid
Acetone 30.1 kg 27.4 kg 2.7 kg
Oils 1.0 0.2 0.8
Sterols 5.2 1.7 3.5
Total 36.3 29.3 7.0 (C) Washing
Acetone used as a wash liquid 17.7 kg
Original Solid
Liquid Wash Liquid Fraction
Acetone 20.4 kg 20.1 kg 0.3 kg Oils 0.8 0.7 0.1
Sterols 3.5 0.3 3.2
Total 24.7 21.1 3.6 (D) Recrystallization (2) followed by Centrifugal Filtration (2)
Original Solid
Liquid Filtrate Fraction
Acetone 157.2 kg 154.9 kg 2.3 kg
Oils 37.1 36.3 0.8
Sterols 4.6 1.5 3.1
Total 198.9 192.7 6.2
Adding up the above:
Original Solid
Liquid Filtrate Fraction
Acetone 157.5 kg 154.9 kg 2.6 kg
Oils 37.2 36.3 0.9
Sterols 7.8 1.5 6.3
Total 202.5 192.7 9.8
% Recovery of Sterols 97.6%
% Recovery of Oils 80.8%
Claims (5)
1. A method of separating sterols in deodorisation distillates of fats and fatty oils by solvent-fractional crystallisation, which comprises centrifugal sedimentation and centrifugal filtration.
2. A method according to claim 1, in which the solvent is selected from C1.4 alkanols, aliphatic carboxylic acid esters, aliphatic ketones and mixtures thereof.
3. A method according to claim 1, in which the centrifugal sedimentation is conducted in a basket-type sedimentation centrifuge, at a centrifugal effect of from 1000 to 1500.
4. A method according to any preceding claim, in which the centrifugal filtration is conducted in a basket-type centrifugal filter, at a centrifugal effect of from 700 to 900.
5. A method according to claim 1, substantially as described in any of the Examples.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14924083A JPS6041694A (en) | 1983-08-17 | 1983-08-17 | Separation method for sterine compounds in deodorized oil and fat distillate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8402452D0 GB8402452D0 (en) | 1984-03-07 |
| GB2145418A true GB2145418A (en) | 1985-03-27 |
| GB2145418B GB2145418B (en) | 1987-03-18 |
Family
ID=15470942
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08402452A Expired GB2145418B (en) | 1983-08-17 | 1984-01-31 | Method of separating sterols from deodorisation distillates of oils |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS6041694A (en) |
| GB (1) | GB2145418B (en) |
| MY (1) | MY100003A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3009417A1 (en) * | 2014-10-13 | 2016-04-20 | LANXESS Deutschland GmbH | Improved method for producing para-thymol |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB895145A (en) * | 1957-08-28 | 1962-05-02 | Eastman Kodak Co | Separation of sterols |
| GB1008767A (en) * | 1961-06-01 | 1965-11-03 | Eastman Kodak Co | Improvements in or relating to sterols and tocopherols |
| GB1030514A (en) * | 1962-03-20 | 1966-05-25 | Eastman Kodak Co | Improvements in or relating to tocopherols and sterols |
| GB1030792A (en) * | 1962-03-20 | 1966-05-25 | Eastman Kodak Co | Improvements in or relating to tocopherols and sterols |
| GB1133903A (en) * | 1966-04-12 | 1968-11-20 | Gen Mills Inc | Process for obtaining tocopherols |
-
1983
- 1983-08-17 JP JP14924083A patent/JPS6041694A/en active Granted
-
1984
- 1984-01-31 GB GB08402452A patent/GB2145418B/en not_active Expired
-
1987
- 1987-06-23 MY MY8700865A patent/MY100003A/en unknown
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB895145A (en) * | 1957-08-28 | 1962-05-02 | Eastman Kodak Co | Separation of sterols |
| GB1008767A (en) * | 1961-06-01 | 1965-11-03 | Eastman Kodak Co | Improvements in or relating to sterols and tocopherols |
| GB1030514A (en) * | 1962-03-20 | 1966-05-25 | Eastman Kodak Co | Improvements in or relating to tocopherols and sterols |
| GB1030792A (en) * | 1962-03-20 | 1966-05-25 | Eastman Kodak Co | Improvements in or relating to tocopherols and sterols |
| GB1133903A (en) * | 1966-04-12 | 1968-11-20 | Gen Mills Inc | Process for obtaining tocopherols |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH047359B2 (en) | 1992-02-10 |
| MY100003A (en) | 1988-10-26 |
| GB8402452D0 (en) | 1984-03-07 |
| JPS6041694A (en) | 1985-03-05 |
| GB2145418B (en) | 1987-03-18 |
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Effective date: 19930131 |