DE3831516A1 - Verfahren zum anreichern von oelsaeure und/oder elaidinsaeure - Google Patents
Verfahren zum anreichern von oelsaeure und/oder elaidinsaeureInfo
- Publication number
- DE3831516A1 DE3831516A1 DE19883831516 DE3831516A DE3831516A1 DE 3831516 A1 DE3831516 A1 DE 3831516A1 DE 19883831516 DE19883831516 DE 19883831516 DE 3831516 A DE3831516 A DE 3831516A DE 3831516 A1 DE3831516 A1 DE 3831516A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- oleic acid
- elaidic
- oleic
- elaidic acid
- 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
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 title claims abstract description 40
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 title claims abstract description 40
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 title claims abstract description 27
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 title claims abstract description 27
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 239000005642 Oleic acid Substances 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims abstract description 21
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 title claims abstract description 20
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 11
- 239000000194 fatty acid Substances 0.000 claims abstract description 11
- 229930195729 fatty acid Natural products 0.000 claims abstract description 11
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 230000005526 G1 to G0 transition Effects 0.000 claims abstract description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000004811 liquid chromatography Methods 0.000 claims abstract description 3
- 239000000741 silica gel Substances 0.000 claims abstract description 3
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 10
- 239000003480 eluent Substances 0.000 claims description 7
- 235000021314 Palmitic acid Nutrition 0.000 claims description 5
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 235000019486 Sunflower oil Nutrition 0.000 claims description 4
- 239000002600 sunflower oil Substances 0.000 claims description 4
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 3
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000012876 carrier material Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 1
- 239000002245 particle Substances 0.000 abstract 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 19
- 239000002253 acid Substances 0.000 description 5
- 238000004237 preparative chromatography Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000003760 tallow Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- XZTJQQLJJCXOLP-UHFFFAOYSA-M sodium;decyl sulfate Chemical compound [Na+].CCCCCCCCCCOS([O-])(=O)=O XZTJQQLJJCXOLP-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/08—Refining
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/32—Bonded phase chromatography
- B01D15/325—Reversed phase
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19883831516 DE3831516A1 (de) | 1988-09-16 | 1988-09-16 | Verfahren zum anreichern von oelsaeure und/oder elaidinsaeure |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19883831516 DE3831516A1 (de) | 1988-09-16 | 1988-09-16 | Verfahren zum anreichern von oelsaeure und/oder elaidinsaeure |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3831516A1 true DE3831516A1 (de) | 1990-03-22 |
| DE3831516C2 DE3831516C2 (enExample) | 1992-02-20 |
Family
ID=6363090
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19883831516 Granted DE3831516A1 (de) | 1988-09-16 | 1988-09-16 | Verfahren zum anreichern von oelsaeure und/oder elaidinsaeure |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3831516A1 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0712651A1 (de) * | 1994-11-15 | 1996-05-22 | K.D. PHARMA GmbH | Verfahren zum Gewinnen eines Stoffes oder einer Stoffgruppe aus einer Mischung |
| WO2000074471A1 (en) * | 1999-06-04 | 2000-12-14 | Consejo Superior De Investigaciones Cientificas | Use of high oleic high stearic oils |
| US7141267B2 (en) | 1999-06-04 | 2006-11-28 | Consejo Superior De Investigaciones Cientificas (Csic) | High oleic/high stearic sunflower oils |
| US7592015B2 (en) | 1999-06-04 | 2009-09-22 | Consejo Superior De Investigaciones Cientificas | Use of high oleic high stearic oils |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0105066A1 (en) * | 1982-10-06 | 1984-04-11 | Uop Inc. | Process for the separation of fatty acids using a solid bed of adsorbent |
| US4524029A (en) * | 1983-09-22 | 1985-06-18 | Uop Inc. | Process for separating fatty acids |
| US4529551A (en) * | 1981-04-10 | 1985-07-16 | Uop Inc. | Process for separating oleic acid from linoleic acid |
-
1988
- 1988-09-16 DE DE19883831516 patent/DE3831516A1/de active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4529551A (en) * | 1981-04-10 | 1985-07-16 | Uop Inc. | Process for separating oleic acid from linoleic acid |
| EP0105066A1 (en) * | 1982-10-06 | 1984-04-11 | Uop Inc. | Process for the separation of fatty acids using a solid bed of adsorbent |
| US4524029A (en) * | 1983-09-22 | 1985-06-18 | Uop Inc. | Process for separating fatty acids |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0712651A1 (de) * | 1994-11-15 | 1996-05-22 | K.D. PHARMA GmbH | Verfahren zum Gewinnen eines Stoffes oder einer Stoffgruppe aus einer Mischung |
| WO2000074471A1 (en) * | 1999-06-04 | 2000-12-14 | Consejo Superior De Investigaciones Cientificas | Use of high oleic high stearic oils |
| US6956155B1 (en) | 1999-06-04 | 2005-10-18 | Consejo Superior De Investigaciones Cientificas | High oleic high stearic plants seeds and oils |
| US7141267B2 (en) | 1999-06-04 | 2006-11-28 | Consejo Superior De Investigaciones Cientificas (Csic) | High oleic/high stearic sunflower oils |
| US7435839B2 (en) | 1999-06-04 | 2008-10-14 | Consejo Superior De Investigaciones Cientificas | High oleic high stearic plants, seads and oils |
| US7592015B2 (en) | 1999-06-04 | 2009-09-22 | Consejo Superior De Investigaciones Cientificas | Use of high oleic high stearic oils |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3831516C2 (enExample) | 1992-02-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |