WO2011039776A1 - Concentrats de haute pureté constitués d'un acide gras polyinsaturé et de son ester, obtenus par complexation du cuivre - Google Patents

Concentrats de haute pureté constitués d'un acide gras polyinsaturé et de son ester, obtenus par complexation du cuivre Download PDF

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Publication number
WO2011039776A1
WO2011039776A1 PCT/IN2010/000626 IN2010000626W WO2011039776A1 WO 2011039776 A1 WO2011039776 A1 WO 2011039776A1 IN 2010000626 W IN2010000626 W IN 2010000626W WO 2011039776 A1 WO2011039776 A1 WO 2011039776A1
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ester
fatty acid
polyunsaturated fatty
acid
solvent
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PCT/IN2010/000626
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English (en)
Inventor
Rakesh Ratnam
Shreeram Joshi
Trupti Terse
P. Suresh
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V. B. Medicare Pvt. Ltd.
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Publication of WO2011039776A1 publication Critical patent/WO2011039776A1/fr

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
    • B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
    • B01J20/3244—Non-macromolecular compounds
    • B01J20/3265—Non-macromolecular compounds with an organic functional group containing a metal, e.g. a metal affinity ligand
    • 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
    • B01D15/38—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving specific interaction not covered by one or more of groups B01D15/265 - B01D15/36
    • B01D15/3804—Affinity chromatography
    • B01D15/3828—Ligand exchange chromatography, e.g. complexation, chelation or metal interaction chromatography
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
    • B01J20/286—Phases chemically bonded to a substrate, e.g. to silica or to polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
    • B01J20/3234—Inorganic material layers
    • B01J20/3236—Inorganic material layers containing metal, other than zeolites, e.g. oxides, hydroxides, sulphides or salts
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
    • B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
    • B01J20/3244—Non-macromolecular compounds
    • 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
    • C11B3/00—Refining fats or fatty oils
    • C11B3/10—Refining fats or fatty oils by adsorption
    • 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

Definitions

  • TECHNICAL FIELD Invention relates to improved methods for isolation and purification of Polyunsaturated fatty acids or/and their esters.
  • the invention also relates to isolation and purification of Docosahexaenoic acid or/and its ester.
  • the invention also relates further to isolation and purification of Polyunsaturated fatty acids including Docosahexaenoic acid from fermentation medium of microorganisms that are grown to produce the said fatty acids.
  • the said method of isolation and purification comprises complexation of polyunsaturated acid, including Docosahexaenoic acid with copper ions.
  • Docosahexaenoic acid (DHA), a long chain polyunsaturated fatty acid (LC-PUFA) is important for brain and eye development. Ingestion of n-3 PUFAs may prevent coronary diseases. Medical studies clearly indicate that these fatty acids have beneficial health aspects, such as improved cardiovascular and immune functions and reduction of cancer, diabetes, and high blood pressure. Recent clinical results have demonstrated that dietary intake of 5.5 g of n-3 PUFAs per week from seafood was linked to a 50% reduction in the risk of primary cardiac arrest. Consequently, oil containing n-3 PUFAs has been in high demand for pharmaceutical and dietetic purposes. These applications require high purity of the PUFA.
  • DHA Docosahexaenoic acid
  • LC-PUFA long chain polyunsaturated fatty acid
  • PUFA enriched PUFA based on the physicochemical properties of FA, such as solubility; polarity; the number, position, and geometric configuration of the double bonds; and chain length. They all include an initial fatty acid pre-concentration stage followed by isolation of the specific PUFA of interest. Concentrates of PUFA are generally most efficiently prepared by urea adduction or low temperature fractional crystallization techniques. The urea fractionation of the fatty acids is mainly based on the degree of unsaturation. There is an inverse correlation between unsaturation and formation of urea crystals. Fractions rich in PUFA can also be obtained by supercritical C02 extraction of neutral lipids or the fatty acid alkyl esters.
  • n-3 PUFA An alternative approach for enrichment of n-3 PUFA is based on enzymatic techniques, such as lipase-catalyzed alcoholysis or interesterification of triglycerides and esterification of glycerol. Urea inclusion is a simple and efficient way to separate PUFA from saturated and monounsaturated FA but by itself is not sufficient to obtain high- purity target PUFA.
  • US 4,189,442 has disclosed a process of separating a fatty acid ester mixture according to degree of unsaturation, said process comprising, amongst other steps, use of macroreticular strong acid cation exchange resin to selectively adsorb fatty acid ester of higher degree of unsaturation and to leave in solution in solvent a fraction of said mixture enriched in content of ester of lesser degree of unsaturation, use of the solvent in each step having the same composition, and said resin having its exchangeable cation substituents consisting essentially of from about 10% to about 90% heavy metal substituents and the remainder alkali metal and/or alkaline earth metal substituents; the solvent and the percentage of heavy metal substituents in the resin being selected to provide selectivity.
  • Heavy metal substituents are selected from the group consisting of silver, copper and gold, and the alkali metal and/or alkaline earth metal substituents are selected from the group consisting of sodium, potassium, barium, calcium and magnesium.
  • the entire ion exchange capacity is saturated by at least two types of metal substituents, one being heavy metals and the other being alkali and alkaline earth metals and not only by one single category or single metal ions.
  • US 4,282,164 has disclosed A process for separating an alkyl carboxylate mixture according to degree of unsaturation comprising, amongst other steps, the steps of applying the mixture to surface of an aluminated silica gel adsorbent to selectively adsorb alkyl carboxylate of higher degree of unsaturation and to leave in solution in solvent a fraction of said mixture enriched in content of alkyl carboxylate of lesser degree of unsaturation and desorbing them by using another solvent said adsorbent being derived from silica gel having a surface area of at least about 100 square meters per gram; said adsorbent being further characterized by a ratio of surface-silicon atoms to aluminum atoms ranging from about 3: 1 to about 20:1, a moisture content less than about 10% by weight, and a particle size ranging from about 200 mesh to about 20 mesh
  • the adsorbing surface comprises a complex mix of metal ions are required for activity; and silver ions are preferentially chosen.
  • Corley et al in a process for separating a first triglyceride comprising a docosahexaenoic acid residue from a second triglyceride has disclosed use of metal ions for co-ordinating with the double bonds of Docosahexaenoic acid residues.
  • Suitable metal ions envisioned by them include metal ions selected from the group consisting of silver, magnesium, and calcium ions. Use of silver or magnesium ions is preferred.
  • objective of this patent is separating triglycerides comprising docosahexaenoic acid residues.
  • the silver ion is the most preferred ion for complexation so far and the systems are multi-ionic systems with a complex mix of heavy metal ions and alkali or alkaline metal ions.
  • the resolving power of Ag+-impregnated silica gel is attributed to the reversible charge-transfer complexation of Ag+ with carbon-carbon double bonds.
  • silver nitrate on silica gel has notable disadvantages under commonly encountered laboratory conditions: It decomposes under light; it is caustic; the Ag+ ion is easily reduced to Ag by PUFA; the silver nitrate is not easily recycled and reused; and silver nitrate is expensive. These disadvantages make silver nitrate unfavorable for commercial production of high-purity DHA.
  • This invention discloses a process of preparing improved purity concentrate of at least one polyunsaturated fatty acid or its ester from a mixture of the said polyunsaturated fatty acid or ester and at least one more other fatty acid or its ester having unsaturation or less unsaturation, the said process comprising steps of: (a) contacting solution of the said mixture in first solvent with copper ions supported on a stationary support in presence of the a first solvent to preferentially adsorb the said polyunsaturated fatty acid or its ester, the said stationary support is one that is capable of impregnation on its surface the copper ions that provide sites for reversible adsorption and desorption with at least one polyunsaturated fatty acid or its ester in presence of the said first solvent for adsorption and a second solvent for desorption, (b) washing away the said other fatty acid or its ester away from the stationary support, (c) desorbing the polyunsaturated fatty acid or its ester from the adsorbent by
  • the said stationary support may be any support that does not adversely react with the constituents of the mixture of fatty acids or their esters subjected to purification and comprises, without limitation, alumina, a resin, silica or Carboxy Methyl Cellulose.
  • the process of this invention may comprise following steps: (a) packing a chromatographic column with a slurry of stationary support carrying copper ions on its surface in a non-polar solvent and equilibrating the said column with the said non-polar solvent, (b) dissolving the said mixture of the said polyunsaturated fatty acid or its ester in the said non-polar solvent and loading the same onto the said stationary support carrying copper ions on its surface causing preferential adsorption of the said polyunsaturated acid or its ester, (c) preferably washing the column with the said non- polar solvent, (d) changing the polarity of the mobile phase by addition of a polar solvent causing desorption/elution, (e) collecting the eluted fractions that contain the polyunsaturated fatty acid or its ester, (f) optionally repeating the steps on the collected eluted fractions in step (e.) from (b.) to (e.) for further improving purity of the said first polyunsaturated fatty acid or
  • polyunsaturated fatty acid or ester of this invention is docosahexaenoic acid or docosahexaenoic acid ester
  • the said adsorbent is copper ions supported by alumina or copper ions supported by a non-ionic polystyrene resin
  • said non-polar solvent is cyclohexane
  • the said polar solvent is acetone.
  • the said docosahexaenoic acid ester may be docosahexaenoic acid methyl ester or docosahexaenoic acid ethyl ester.
  • the process of this invbention illustrate here comprises preparing improved purity concentrate of docosahexaenoic acid or its ester from a mixture of the said docosahexenoic acid or its ester and at least one more other fatty acid or its ester having unsaturation or less unsaturation, the said process comprising steps of: (a) packing a column with slurry of an adsorbent consisting of copper ions supported by alumina or copper ions supported by a non-ioninc polystyrene resin that is further equilibrated with cyclohexane, (b) contacting the said mixture dissolved in cyclohexane with the said adsorbent to get the said docosahexaenoic acid or its ester adsorbed on to the said adsorbent, (c) preferably washing the column after adsorption with cyclohexane, (d) changing the polarity of the mobile phase by addition of acetone to cause desorption
  • the mixture of the said polyunsaturated fatty acid or ester and at least one more other fatty acid or its ester having unsaturation or less unsaturation may be derived from a marine oil, which may be, including without limitation, fish oil, an oil extracted from a marine algae selcted for its ability of a heterotropic growth in a medium haing less salinity than sea water.
  • a Thraustochytriale may be a Thraustochytrium or Schizochytrium.
  • the process of this invention is surprisingly simple, does not require intricate balance of heavy metal ions with alkali or alkaline earth metal ions nor does it require use of silver metal ions.
  • the process of this invention comprises isolation of one or more of an ester of one or more of a polyunsaturated fatty acid or a polyunsaturated free fatty acid by low pressure chromatography on a stationary support with copper complexation from other ester of fatty acid or other fatty acid.
  • Catalyst of this invention is different from the catalyst used by US 4,189,442 for separating a fatty acid ester mixture according to degree of unsaturation and by US 4,282,164 for a process for separating an alkyl carboxylate mixture according to degree of unsaturation because in present invention, the Copper ion supported by the stationary support of this invention participates in the adsorption or desorption with desired unsaturated fatty acid in a mixture containing the said at least one unsaturated fatty acid and the said at least one other fatty acid. Thus, only one ion participates in adsorption and desorption process of desired unsaturated fatty acid even when stationary support used is A1 2 0 3 .
  • A1 2 0 can not participate in adsorption as each particle of it, is fully covered by Cu + ion by complexation, whereas, in above mentioned patent documents, both the metal, ions are required to achieve the disclosed adsorption and desorption of desired unsaturated fatty acid from the mixture.
  • non-ionic resin as support for copper ions, it is clear that except copper ion, there is no metal ion other than the copper ion that can be contemplated to be participating in the process of adsorption and desorption.
  • the invention further comprises isolation of one or more of an ester of one or more of a polyunsaturated fatty acid or free fatty acid from a marine oil.
  • the invention comprises obtaining highly pure ester of Docosahexaenoic acid)that is more than 95% pure.
  • the isolated ester may be hydrolysed to get acid.
  • the marine oil may be a fish oil or an oil extracted from a marine algae selcted for its ability of a heterotropic growth in a medium haing less salinity than sea water.
  • Such a Thraustochytriale may be a Thraustochytrium or Schizochytrium.
  • copper is complexed on a variety of stationary media / supports that on one hand would provide complexation with copper, do not adversely react with polyunsaturated fatty acids and produce adsorption sites for polyunsaturated fatty acids that provide for reversible adsorption and desorption by using appropriate eluent liquid.
  • the stationary support of this invention includes, without limitation, alumina, a resin, silica, Carboxy Methyl Cellulose and the like, complexed or impregnated with or substituted with copper ions on the surface. Many prior art methods of achiving copper ion impregnation on stationary supports are available.
  • they include activating the stationary support at an elevated temperature, usually up to 150°C under vacuum for a period of time such as 24 hours. Then the activated support is cooled to ambient temperature, suspended in saturated copper sulphate solution, conveniently at is achieved, usually for 16 hours, at room temperature. The impregnated stationary support is then filtered and dried at about 150°C preferably in a vaccum drying oven (0.67 kPa) till moisture less than 1%, cooled to room temperature under same pressure and kept in a desiccator until used.
  • illustratin is given with Alumina and non-ionic resins as stationary supports. However, other stationary supports may also be used that will nto adversely react with polyunsaturated fatty acids or their esters.
  • Non- ionic resin used here is a non-ionic polystyrene resin Tulsion ADS600 from Thermax India. Highly pure Docosahexaenoic acid (DHA) (more than 95% purity) was obtained from marine algal oil using low pressure copper complexation chromatography. High pressure also can be used, however best results have been obtained with low pressure chromatography. An enriched fraction of PUFA containing 75% DHA, 12% Docosapentaenoic acid (DPA), 6% Docosatrienoic acid (DTA) & 2% Palmitic acid by weight was esterified and loaded on Cu impregnated alumina. Cyclohexane & acetone were used as mobile phase.
  • DHA Docosahexaenoic acid
  • DTA Docosatrienoic acid
  • DHA esters with a purity of >95 % & a recovery of >65% were obtained.
  • the process of this invention may have to be repeated twice or a more number of times depending on what is the initial purity of the composition to be purified.
  • Alumina / Resin is activated by heating to 150°C under vacuum for 24 hours. Then the Alumina / Resin is cooled to ambient temperature. 1 :10 w/v of resin or Alumina to saturated copper sulphate solution in water is stirred for 16 hours at room temperature. The Alumina / Resin is then filtered and dried at 150°C in vaccum drying oven (0.67 kPa) till moisture less than 1%, cooled to room temperature under same pressure and was kept in a desiccator. The copper sulphate impregnated Alumina / Resin is now ready for column chromatography. Resin used here is a non-ionic polystyrene resin Tulsion ADS 600 from Thermax India.
  • a DHA methyl ester enriched composition of PUFA containing 75 % of DHA residue by weight was dissolved in cyclohexane and was loaded onto Cu-alumina column.
  • the feed concentration was 20%.
  • the capacity of the adsorbent was lOg DHA residue/L of bed volume.
  • Flow rate was maintained between 1-2 BV (Bed volume)/hr for all operations. Washing was done using 1 BV of cyclohexane.
  • the polarity of the mobile phase was changed by addition of acetone, which caused desorption/elution.
  • Fractions were collected at the column outlet and analysed for purity by GC (Gas chromatography). DHA methyl ester with a purity of more than 95 % & a recovery of more than 65% was obtained. Similar results were obtained with 75% DHA ethyl ester as feed.
  • DHA methyl ester enriched composition of PUFA esters containing 40% of DHA residue by weight was dissolved in cyclohexane and was loaded onto Cu-alumina column.
  • the feed concentration was 20%.
  • the capacity of the adsorbent was lOg DHA residue/L of bed volume.
  • Flow rate was maintained between 1-2 BV/hr for all operations. Washing was done using 1 BV of cyclohexane.
  • the polarity of the mobile phase was changed by addition of acetone which caused desorption/elution.
  • Fractions were collected at the column outlet and analysed for purity by GC.
  • DHA methyl ester with a purity of more than 70 % & a recovery of more than 65% was obtained. Similar results were obtained with 40% DHA ethyl ester as feed. The purity was further enhanced by repeating the column operation as shown in Example 1.
  • a DHA methyl ester enriched composition of PUFA esters containing 72 % DHA residue by weight was dissolved ) in cyclohexane and was loaded onto Cu-impregnated non-ionic resin, Tusion ADS 600 from Thermax India, which is a non-ionic polystyrenic adsorbent.
  • the feed concentration was 20%.
  • the capacity of the adsorbent was 5g DHA residue/L of bed volume.
  • Flow rate was maintained between 1-2 BV (Bed volume)/hr for all operations. Washing was done using 1 BV of cyclohexane.
  • the polarity of the mobile phase was changed by addition of acetone, which caused desorption/elution. Fractions were collected at the column outlet and analysed for purity by GC (Gas chromatography). DHA methyl ester with a purity of more than 86 % & a recovery of more than 72% was obtained.

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  • Chemical Kinetics & Catalysis (AREA)
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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Microbiology (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)

Abstract

L'invention concerne un procédé pour préparer un concentrat à pureté améliorée constitué d'au moins un acide gras polyinsaturé ou de son ester, à partir d'un mélange dudit acide gras polyinsaturé ou de son ester et d'au moins un autre acide gras supplémentaire ou son ester, ces derniers présentant un niveau d'insaturation élevé ou faible. Ce procédé consiste à utiliser des ions cuivre imprégnés sur un support fixe pour une adsorption préférentielle ou sélective desdits acides gras polyinsaturés dans des solvants à prédominance non polaire et pour une désorption dans des solvants polaires. Le mélange dudit acide gras polyinsaturé ou de son ester et d'au moins un autre acide gras supplémentaire ou son ester, ces derniers présentant un niveau d'insaturation élevé ou faible, peut être issu d'une huile marine, qui peut être, entre autres, une huile de poisson ou une huile extraite à partir d'une algue marine sélectionnée pour sa capacité à croître de manière hétérotropique dans un milieu dont la salinité est inférieure à celle de l'eau de mer. Une telle algue de l'ordre des Thraustochytriales peut être un Thraustochytrium ou un Schizochytrium.
PCT/IN2010/000626 2009-09-17 2010-09-16 Concentrats de haute pureté constitués d'un acide gras polyinsaturé et de son ester, obtenus par complexation du cuivre WO2011039776A1 (fr)

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IN2155MU2009 2009-09-17

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019242873A1 (fr) 2018-06-21 2019-12-26 Nuseed Pty Ltd. Compositions d'acides gras polyinsaturés enrichies en dha
CN110975839A (zh) * 2019-12-04 2020-04-10 江苏新宇生物科技有限公司 一种提高脱铜离子效率的新型树脂材料及其制备方法
CN113956919A (zh) * 2021-11-15 2022-01-21 山东禹王制药有限公司 一种高纯度不饱和脂肪酸的制备方法

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US4189442A (en) * 1978-10-18 1980-02-19 The Procter & Gamble Company Separation of fatty acid esters
US4784807A (en) * 1987-07-06 1988-11-15 Uop Inc. Process for separating triglylcerides by degree of unsaturation
US4961881A (en) * 1988-02-17 1990-10-09 Uop Process for separating triglycerides and regenerating absorbent used in said separation process
US6399803B1 (en) * 1999-02-26 2002-06-04 Omegatech, Inc. Process for separating a triglyceride comprising a docosahexaenoic acid residue from a mixture of triglycerides

Patent Citations (4)

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Publication number Priority date Publication date Assignee Title
US4189442A (en) * 1978-10-18 1980-02-19 The Procter & Gamble Company Separation of fatty acid esters
US4784807A (en) * 1987-07-06 1988-11-15 Uop Inc. Process for separating triglylcerides by degree of unsaturation
US4961881A (en) * 1988-02-17 1990-10-09 Uop Process for separating triglycerides and regenerating absorbent used in said separation process
US6399803B1 (en) * 1999-02-26 2002-06-04 Omegatech, Inc. Process for separating a triglyceride comprising a docosahexaenoic acid residue from a mixture of triglycerides

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Title
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 2006:737915 *
ZHANG, Y.X. ET AL.: "Purification of arachidonic acid from fungal single-cell oil via A12O3-supported CUSO4 column chromatography", JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, vol. 83, no. 7, 2006, pages 659 - 662 *
ZHOU, Y. ET AL.: "Preparation of high content a-ethyl linolenate product", RIYONG HUAXUE GONGYE, vol. 35, no. 4, 2005, pages 216 - 218 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019242873A1 (fr) 2018-06-21 2019-12-26 Nuseed Pty Ltd. Compositions d'acides gras polyinsaturés enrichies en dha
EP3586640A1 (fr) 2018-06-21 2020-01-01 Nuseed Pty Ltd Compositions d'acides gras polyinsaturés enrichies en dha
US11872201B2 (en) 2018-06-21 2024-01-16 Nuseed Nutritional Us Inc. DHA enriched polyunsaturated fatty acid compositions
CN110975839A (zh) * 2019-12-04 2020-04-10 江苏新宇生物科技有限公司 一种提高脱铜离子效率的新型树脂材料及其制备方法
CN113956919A (zh) * 2021-11-15 2022-01-21 山东禹王制药有限公司 一种高纯度不饱和脂肪酸的制备方法

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