CN117209376A - Method for completely separating oleic acid and linoleic acid - Google Patents
Method for completely separating oleic acid and linoleic acid Download PDFInfo
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- CN117209376A CN117209376A CN202310990943.2A CN202310990943A CN117209376A CN 117209376 A CN117209376 A CN 117209376A CN 202310990943 A CN202310990943 A CN 202310990943A CN 117209376 A CN117209376 A CN 117209376A
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- oleic acid
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- linoleic acid
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- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 title claims abstract description 47
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 title claims abstract description 47
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 title claims abstract description 47
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 239000005642 Oleic acid Substances 0.000 title claims abstract description 47
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 title claims abstract description 47
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 title claims abstract description 47
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 title claims abstract description 27
- 235000020778 linoleic acid Nutrition 0.000 title claims abstract description 26
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 19
- 239000011259 mixed solution Substances 0.000 claims abstract description 14
- 238000010262 high-speed countercurrent chromatography Methods 0.000 claims abstract description 12
- 230000005526 G1 to G0 transition Effects 0.000 claims abstract description 11
- 238000002347 injection Methods 0.000 claims abstract description 3
- 239000007924 injection Substances 0.000 claims abstract description 3
- 238000005191 phase separation Methods 0.000 claims abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 5
- 238000007872 degassing Methods 0.000 claims description 4
- 238000001514 detection method Methods 0.000 claims description 4
- 238000002390 rotary evaporation Methods 0.000 claims description 4
- 238000001291 vacuum drying Methods 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 6
- 238000005516 engineering process Methods 0.000 abstract description 6
- 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 abstract description 4
- 229960004232 linoleic acid Drugs 0.000 description 18
- 239000000203 mixture Substances 0.000 description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000005456 glyceride group Chemical group 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000010775 animal oil Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 235000019871 vegetable fat Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- YZAZXIUFBCPZGB-QZOPMXJLSA-N (z)-octadec-9-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O YZAZXIUFBCPZGB-QZOPMXJLSA-N 0.000 description 1
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021319 Palmitoleic acid Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 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 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 235000004626 essential fatty acids Nutrition 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000021315 omega 9 monounsaturated fatty acids Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Abstract
The application relates to a method for completely separating oleic acid and linoleic acid, which comprises the following steps: fully shaking the solvent system, standing for phase separation, and collecting an upper phase and a lower phase separately; dissolving 70-80% of high-purity oleic acid in an upper phase, separating by adopting high-speed countercurrent chromatography, and from sample injection, connecting forward rotation, wherein the upper phase is a stationary phase, and a lower phase is a mobile phase to obtain a mixed solution of linoleic acid and the lower phase; then the reverse rotation is carried out, the lower phase is the stationary phase, the upper phase is the mobile phase, the mixed solution of oleic acid and the upper phase is obtained, and the lower phase and the upper phase are removed, so that linoleic acid and oleic acid are respectively obtained. The application firstly utilizes the high-speed countercurrent chromatography technology to separate and purify 70-80% high-purity oleic acid to obtain the oleic acid with the purity of more than 99%, the reagents of a solvent system can be recycled, and in theory, the oleic acid can be recycled by 100%.
Description
The application relates to a method for completely separating oleic acid and linoleic acid, which is a divisional application with the application number of 2019108600016 and the application date of 20190911.
Technical Field
The application belongs to the technical field of unsaturated fatty acid processing, and particularly relates to a method for completely separating oleic acid and linoleic acid.
Background
Oleic acid (Oleic acid) is a monounsaturated omega-9 fatty acid containing 18 carbon atoms and 1 double bond. Oleic acid is mainly derived from nature and exists in animal and vegetable oils and fats in the form of glycerides. And (3) saponifying and acidifying the grease with high oleic acid content to separate to obtain oleic acid. Natural oleic acid has a certain effect on softening blood vessels and provides the energy required by the body. Has effects in reducing blood sugar, regulating blood lipid, and reducing cholesterol.
Linoleic acid (linolic acid) is a polyunsaturated omega-6 essential fatty acid containing 18 carbon atoms and 2 double bonds. Linoleic acid is present in animal and vegetable oils and fats in the form of glycerides together with other fatty acids, and is a main component of drying oils and semi-drying oils such as linseed oil and cottonseed oil which are composed in the form of glycerides. Can be used for reducing blood cholesterol and preventing atherosclerosis.
The content of oleic acid required by the medicinal oleic acid is more than 98%, myristic acid is less than 0.5%, palmitic acid is less than 0.5%, palmitoleic acid is less than 0.5%, stearic acid is less than 0.5%, linoleic acid is less than 0.5%, and linolenic acid is less than 0.5%. The traditional separation and purification method is difficult to reduce the linoleic acid content to below 0.5 percent.
The high-speed countercurrent chromatography (HSCCC) technology is a novel separation and purification technology based on the liquid-liquid distribution principle, does not need any solid support or carrier, and has the advantages of liquid stationary phase and mobile phase and no irreversible adsorption.
Disclosure of Invention
The application aims to provide a method for completely separating oleic acid and linoleic acid, which adopts a high-speed countercurrent chromatography technology and obtains oleic acid with purity more than 99 percent from 70-80 percent of high-purity oleic acid by one step of separation and purification of a solvent system.
The application provides a method for completely separating oleic acid and linoleic acid, which comprises the following steps:
fully shaking the solvent system, standing for phase separation, and collecting an upper phase and a lower phase separately; dissolving 70-80% of high-purity oleic acid in an upper phase, separating by adopting high-speed countercurrent chromatography, and from sample injection, connecting forward rotation, wherein the upper phase is a stationary phase, and a lower phase is a mobile phase to obtain a mixed solution of linoleic acid and the lower phase; then the reverse rotation is carried out, the lower phase is a stationary phase, the upper phase is a mobile phase, the mixed solution of oleic acid and the upper phase is obtained, and the lower phase and the upper phase are removed to obtain linoleic acid and oleic acid respectively;
wherein the solvent system is prepared by mixing n-hexane or n-heptane, acetonitrile or ethanol according to the volume ratio of 4-8:4-8.
And carrying out ultrasonic degassing treatment on the upper and lower phases obtained by separation and collection.
The conditions of the high-speed countercurrent chromatography are as follows: the rotation speed is 800rpm; the column temperature is 25 ℃; the flow rate of the mobile phase is 10mL/min; the detection wavelength of the detector was 214nm.
The process conditions for removing the upper phase and the lower phase are as follows: rotary evaporation vacuum drying is carried out at 50 deg.c and-0.085 MPa.
The solvent system is determined by the solubility of linoleic acid and oleic acid in the mutually immiscible two-phase solvents.
Advantageous effects
(1) The application firstly utilizes the high-speed countercurrent chromatography technology to separate and purify the oleic acid with the purity of more than 99 percent from the commercially available 70-80 percent high-purity oleic acid.
(2) The high-speed countercurrent chromatography technology has the advantages of no sample loss, no pollution, high efficiency, large preparation amount, recyclable solvent and the like.
(3) The solvent system reagent adopted in the application can be recycled, has good environmental protection function, and can realize 100% recovery in theory.
Detailed Description
The application will be further illustrated with reference to specific examples. It is to be understood that these examples are illustrative of the present application and are not intended to limit the scope of the present application. Furthermore, it should be understood that various changes and modifications can be made by one skilled in the art after reading the teachings of the present application, and such equivalents are intended to fall within the scope of the application as defined in the appended claims.
The reagents and instrumentation used in the examples were as follows:
reagent: n-hexane, n-heptane, acetonitrile and ethanol are all analytically pure reagents produced by national pharmaceutical group chemical reagent company, and 70-80% of high-purity oleic acid is a commercial product;
instrument: the high-speed countercurrent chromatograph is TBE-300C model high-speed countercurrent chromatograph manufactured by Shanghai Tongtian Biotechnology Co., ltd.
Example 1
N-hexane, acetonitrile and water are mixed according to the volume ratio of 6:6:2, adding the mixture into a separating funnel, fully shaking, standing and phase-separating to obtain a two-phase mixed solution, separately collecting an upper phase solvent and a lower phase solvent, respectively placing the two phases of solvents in an ultrasonic oscillator for ultrasonic degassing treatment, dissolving 70-80% of high-purity oleic acid in the upper phase solvent, and separating by adopting high-speed countercurrent chromatography: positive rotation is carried out for 0-60 minutes, the upper phase is a stationary phase, the lower phase is a mobile phase, and the mixed solution of linoleic acid and the lower phase is obtained; the mixture is reversely connected and positively rotated for 60 to 90 minutes, the lower phase is a stationary phase, the upper phase is a mobile phase, and the mixture of oleic acid and the upper phase is obtained; wherein the chromatographic conditions are set as follows: the rotation speed is 800rpm; column temperature 25 ℃; the flow rate of the mobile phase is 10mL/min; the detection wavelength of the detector is 214nm; and then placing the obtained mixed solution of linoleic acid and the lower phase and the mixed solution of oleic acid and the upper phase in a rotary evaporator, and carrying out rotary evaporation vacuum drying under the conditions of water bath temperature of 50 ℃ and vacuum pressure of-0.085 MPa to remove the lower phase and the upper phase, thereby obtaining linoleic acid and oleic acid products respectively.
The oleic acid product obtained in this example was analyzed for purity by HPLC, and the results showed that: oleic acid purity was 99.42% (with linoleic acid content of 0.12%).
Example 2
N-heptane, ethanol and water are mixed according to the volume ratio of 8:8:1, adding the mixture into a separating funnel, fully shaking, standing and phase-separating to obtain a two-phase mixed solution, separately collecting an upper phase solvent and a lower phase solvent, respectively placing the two phases of solvents into an ultrasonic oscillator for ultrasonic degassing treatment, dissolving 70-80% of high-purity oleic acid into the upper phase solvent, and separating by adopting high-speed countercurrent chromatography: positive rotation is carried out for 0-50 minutes, the upper phase is a stationary phase, the lower phase is a mobile phase, and the mixed solution of linoleic acid and the lower phase is obtained; the mixture is reversely connected and positively rotated for 50-80 minutes, the lower phase is a stationary phase, the upper phase is a mobile phase, and the mixture of oleic acid and the upper phase is obtained; wherein the chromatographic conditions are set as follows: the rotation speed is 800rpm; column temperature 25 ℃; the flow rate of the mobile phase is 10mL/min; the detection wavelength of the detector is 214nm; and then placing the obtained mixed solution of linoleic acid and the lower phase and the mixed solution of oleic acid and the upper phase in a rotary evaporator, and carrying out rotary evaporation vacuum drying under the conditions of water bath temperature of 50 ℃ and vacuum pressure of-0.085 MPa to remove the lower phase and the upper phase, thereby obtaining linoleic acid and oleic acid products.
The oleic acid product obtained in this example was analyzed for purity by HPLC, and the results showed that: oleic acid purity was 99.32% (with linoleic acid content of 0.08%).
Claims (4)
1. A method of completely separating oleic acid and linoleic acid comprising:
fully shaking the solvent system, standing for phase separation, and collecting an upper phase and a lower phase separately; dissolving 70-80% of high-purity oleic acid in an upper phase, separating by adopting high-speed countercurrent chromatography, and from sample injection, connecting forward rotation, wherein the upper phase is a stationary phase, and a lower phase is a mobile phase to obtain a mixed solution of linoleic acid and the lower phase; then the reverse rotation is carried out, the lower phase is the stationary phase, the upper phase is the mobile phase, the mixed solution of oleic acid and the upper phase is obtained, and the lower phase and the upper phase are removed, so that linoleic acid and oleic acid are respectively obtained.
Wherein the solvent system is prepared by mixing n-hexane or n-heptane, acetonitrile or ethanol according to the volume ratio of 4-8:4-8.
2. A method for completely separating oleic acid and linoleic acid according to claim 1, wherein: and carrying out ultrasonic degassing treatment on the upper and lower phases obtained by separation and collection.
3. A method for completely separating oleic acid and linoleic acid according to claim 1, wherein: the conditions of the high-speed countercurrent chromatography are as follows: the rotation speed is 800rpm; the column temperature is 25 ℃; the flow rate of the mobile phase is 10mL/min; the detection wavelength of the detector was 214nm.
4. A method for completely separating oleic acid and linoleic acid according to claim 1, wherein: the process conditions for removing the upper phase and the lower phase are as follows: rotary evaporation vacuum drying is carried out at 50 deg.c and-0.085 MPa.
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| CN202310990943.2A CN117209376A (en) | 2019-09-11 | 2019-09-11 | Method for completely separating oleic acid and linoleic acid |
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| CN202310990943.2A CN117209376A (en) | 2019-09-11 | 2019-09-11 | Method for completely separating oleic acid and linoleic acid |
| CN201910860001.6A CN110590545B (en) | 2019-09-11 | 2019-09-11 | Method for completely separating oleic acid and linoleic acid |
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| CN111635308B (en) * | 2020-06-20 | 2023-04-07 | 四川中海茂农业开发有限公司 | Method for co-producing and preparing linoleic acid and alpha-linolenic acid from idesia polycarpa seed oil |
| CN115490588B (en) * | 2022-09-18 | 2024-02-06 | 西北农林科技大学 | Method for separating various unsaturated fatty acids from torreya seed oil |
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| CH663951A5 (en) * | 1984-10-10 | 1988-01-29 | Nestle Sa | PROCESS FOR THE SELECTIVE ENRICHMENT OF POLYUNSATURATED FATTY ACIDS IN A MIXTURE CONTAINING ENRICHED FRACTION FATTY ACIDS AND COMPOSITIONS CONTAINING THE SAME. |
| DE4206539A1 (en) * | 1992-03-02 | 1993-09-09 | K D Pharma Gmbh | METHOD FOR OBTAINING UNSATURATED FATTY ACIDS |
| US20070065526A1 (en) * | 2005-09-19 | 2007-03-22 | Gow Robert T | Methods and compositions comprising Panax species |
| US20070213298A1 (en) * | 2006-02-07 | 2007-09-13 | Universitetet I Oslo | Omega 3 |
| NZ556769A (en) * | 2007-07-27 | 2010-01-29 | Ind Res Ltd | Use of ionic liquids for extraction or fractionation of lipids |
| CN103086873B (en) * | 2013-01-11 | 2015-09-16 | 国家海洋局第三海洋研究所 | High speed adverse current chromatogram is separated preparation high purity DHA method |
| CN104031013B (en) * | 2014-06-17 | 2016-08-24 | 浙江工业大学 | A kind of utilize the isolated and purified method preparing salvianolic acid B and rosmarinic acid of high speed adverse current chromatogram |
| CA2994266A1 (en) * | 2015-07-31 | 2017-02-09 | Scientific Holdings, Llc | Botanical identification method and system |
| CN106542991A (en) * | 2016-10-21 | 2017-03-29 | 哈尔滨理工大学 | A kind of high-speed counter-current extracts the method and purposes of high-purity linoleic acid and its preparation in Lignum Xanthoceratiss seed kernel oil |
| CN107739296B (en) * | 2017-09-30 | 2020-11-24 | 武汉欧米嘉生物医药有限公司 | Method for collecting oleic acid from tea oil |
| CN108164415B (en) * | 2017-12-28 | 2021-07-09 | 上海同田生物技术股份有限公司 | Method for completely separating EPA and DHA from fish oil |
| CN108864234B (en) * | 2018-07-06 | 2020-06-26 | 厦门医学院 | Method for separating inosine from ascidians plicata |
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| CN110590545B (en) | 2023-08-29 |
| CN110590545A (en) | 2019-12-20 |
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