DE2352346A1 - Verfahren zur erhoehung des gehaltes an gebundenen mehrfach ungesaettigten fettsaeuren von geniessbaren oelen - Google Patents
Verfahren zur erhoehung des gehaltes an gebundenen mehrfach ungesaettigten fettsaeuren von geniessbaren oelenInfo
- Publication number
- DE2352346A1 DE2352346A1 DE19732352346 DE2352346A DE2352346A1 DE 2352346 A1 DE2352346 A1 DE 2352346A1 DE 19732352346 DE19732352346 DE 19732352346 DE 2352346 A DE2352346 A DE 2352346A DE 2352346 A1 DE2352346 A1 DE 2352346A1
- Authority
- DE
- Germany
- Prior art keywords
- oil
- polar solvent
- solvent
- bound
- fraction
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 20
- 239000008157 edible vegetable oil Substances 0.000 title claims description 5
- 239000000194 fatty acid Substances 0.000 title description 6
- 235000014113 dietary fatty acids Nutrition 0.000 title description 5
- 229930195729 fatty acid Natural products 0.000 title description 5
- 150000004665 fatty acids Chemical class 0.000 title description 5
- 239000003921 oil Substances 0.000 claims description 54
- 235000019198 oils Nutrition 0.000 claims description 54
- 239000002798 polar solvent Substances 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 25
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 17
- 235000020778 linoleic acid Nutrition 0.000 claims description 16
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims description 15
- 239000012454 non-polar solvent Substances 0.000 claims description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 10
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 235000013310 margarine Nutrition 0.000 claims description 4
- 239000003264 margarine Substances 0.000 claims description 4
- 235000020238 sunflower seed Nutrition 0.000 claims description 4
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims description 3
- -1 N-substituted amide Chemical class 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 235000012343 cottonseed oil Nutrition 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- 235000013305 food Nutrition 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000002385 cottonseed oil Substances 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000003495 polar organic solvent Substances 0.000 claims description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 2
- 235000014438 salad dressings Nutrition 0.000 claims description 2
- 239000010779 crude oil Substances 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 239000012188 paraffin wax Substances 0.000 claims 1
- 238000000605 extraction Methods 0.000 description 19
- 125000005456 glyceride group Chemical group 0.000 description 11
- 239000007788 liquid Substances 0.000 description 9
- 239000004215 Carbon black (E152) Substances 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 150000002430 hydrocarbons Chemical class 0.000 description 8
- 239000003925 fat Substances 0.000 description 7
- 235000019197 fats Nutrition 0.000 description 7
- 235000019486 Sunflower oil Nutrition 0.000 description 6
- 239000002600 sunflower oil Substances 0.000 description 6
- 235000019485 Safflower oil Nutrition 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 239000003813 safflower oil Substances 0.000 description 5
- 235000005713 safflower oil Nutrition 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 4
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 229960004488 linolenic acid Drugs 0.000 description 4
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000005192 partition Methods 0.000 description 3
- 241000208818 Helianthus Species 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 229940049918 linoleate Drugs 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
- HCSCWJCZRCSQFA-UHFFFAOYSA-N 1-methylpyrrolidin-2-one;hydrate Chemical compound O.CN1CCCC1=O HCSCWJCZRCSQFA-UHFFFAOYSA-N 0.000 description 1
- HXMVNCMPQGPRLN-UHFFFAOYSA-N 2-hydroxyputrescine Chemical compound NCCC(O)CN HXMVNCMPQGPRLN-UHFFFAOYSA-N 0.000 description 1
- 244000020518 Carthamus tinctorius Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 241000282620 Hylobates sp. Species 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 239000008162 cooking oil Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000004626 essential fatty acids Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 101150046463 gsiA gene Proteins 0.000 description 1
- 229940116364 hard fat Drugs 0.000 description 1
- 239000010514 hydrogenated cottonseed oil Substances 0.000 description 1
- 239000008173 hydrogenated soybean oil Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 235000004213 low-fat Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000016087 ovulation Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/001—Spread compositions
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/015—Reducing calorie content; Reducing fat content, e.g. "halvarines"
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
- C11B7/0008—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
- C11B7/0008—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents
- C11B7/0033—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents in solvents containing other heteroatoms in their molecule
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Edible Oils And Fats (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4803972A GB1444551A (en) | 1972-10-18 | 1972-10-18 | Solvent extraction of glyceride oils |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2352346A1 true DE2352346A1 (de) | 1974-05-02 |
Family
ID=10447145
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732352346 Pending DE2352346A1 (de) | 1972-10-18 | 1973-10-18 | Verfahren zur erhoehung des gehaltes an gebundenen mehrfach ungesaettigten fettsaeuren von geniessbaren oelen |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3892789A (enExample) |
| JP (1) | JPS4974206A (enExample) |
| AU (1) | AU471905B2 (enExample) |
| BE (1) | BE806254A (enExample) |
| BR (1) | BR7308116D0 (enExample) |
| CA (1) | CA1022185A (enExample) |
| DE (1) | DE2352346A1 (enExample) |
| ES (1) | ES419773A1 (enExample) |
| FR (1) | FR2203593B1 (enExample) |
| GB (1) | GB1444551A (enExample) |
| IE (1) | IE38372B1 (enExample) |
| IT (1) | IT1020517B (enExample) |
| LU (1) | LU68642A1 (enExample) |
| NL (1) | NL7314265A (enExample) |
| SU (1) | SU606552A3 (enExample) |
| ZA (1) | ZA737991B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9212788D0 (en) * | 1992-06-16 | 1992-07-29 | Efamol Holdings | Separation of unsaturates |
| US5405633A (en) * | 1992-10-08 | 1995-04-11 | Skw Trostberg Aktiengesellschaft | Process for the extraction of fats and oils |
| ES2080685B1 (es) * | 1994-02-11 | 1996-09-01 | Consejo Superior Investigacion | Procedimiento para la separacion no destructiva de los pigmentos cloroplasticos y la fraccion glicerica en aceites y oleorresinas vegetales. |
| US5928478A (en) * | 1998-09-14 | 1999-07-27 | Berg; Lloyd | Separation of linoleic acid from linolenic acid by azeotropic distillation |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2200391A (en) * | 1939-01-17 | 1940-05-14 | Pittsburgh Plate Glass Co | Solvent extraction of glyceride oils |
| US2573900A (en) * | 1948-11-26 | 1951-11-06 | Pittsburgh Plate Glass Co | Treatment of glyceride oils |
| US3376326A (en) * | 1964-12-31 | 1968-04-02 | Procter & Gamble | Interesterification of glycerides |
-
1972
- 1972-10-18 GB GB4803972A patent/GB1444551A/en not_active Expired
-
1973
- 1973-10-12 IE IE1821/73A patent/IE38372B1/xx unknown
- 1973-10-15 US US406748A patent/US3892789A/en not_active Expired - Lifetime
- 1973-10-15 AU AU61372/73A patent/AU471905B2/en not_active Expired
- 1973-10-15 ZA ZA00737991A patent/ZA737991B/xx unknown
- 1973-10-16 CA CA183,530A patent/CA1022185A/en not_active Expired
- 1973-10-17 BR BR8116/73A patent/BR7308116D0/pt unknown
- 1973-10-17 IT IT70076/73A patent/IT1020517B/it active
- 1973-10-17 NL NL7314265A patent/NL7314265A/xx not_active Application Discontinuation
- 1973-10-17 FR FR7337080A patent/FR2203593B1/fr not_active Expired
- 1973-10-17 SU SU731967539A patent/SU606552A3/ru active
- 1973-10-18 DE DE19732352346 patent/DE2352346A1/de active Pending
- 1973-10-18 JP JP48117343A patent/JPS4974206A/ja active Pending
- 1973-10-18 BE BE136844A patent/BE806254A/xx unknown
- 1973-10-18 ES ES419773A patent/ES419773A1/es not_active Expired
- 1973-10-18 LU LU68642A patent/LU68642A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| LU68642A1 (enExample) | 1974-05-09 |
| BE806254A (fr) | 1974-04-18 |
| GB1444551A (en) | 1976-08-04 |
| ES419773A1 (es) | 1976-03-01 |
| AU471905B2 (en) | 1976-05-06 |
| US3892789A (en) | 1975-07-01 |
| ZA737991B (en) | 1975-05-28 |
| FR2203593A1 (enExample) | 1974-05-17 |
| AU6137273A (en) | 1975-04-17 |
| JPS4974206A (enExample) | 1974-07-17 |
| NL7314265A (enExample) | 1974-04-22 |
| IE38372L (en) | 1974-04-18 |
| FR2203593B1 (enExample) | 1978-02-17 |
| IE38372B1 (en) | 1978-03-01 |
| IT1020517B (it) | 1977-12-30 |
| CA1022185A (en) | 1977-12-06 |
| SU606552A3 (ru) | 1978-05-05 |
| BR7308116D0 (pt) | 1974-06-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |