The present invention provides a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product from a feed mixture, which process comprises passing the feed mixture through one or more chromatographic columns containing, as eluent, an aqueous organic solvent, wherein the temperature of at least one of the chromatographic columns through which the feed mixture is passed is greater than room temperature.
C11B 7/00 - Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
C11B 3/10 - Refining fats or fatty oils by adsorption
B01D 15/18 - Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns
B01D 15/38 - Selective adsorption, e.g. chromatography characterised by the separation mechanism involving specific interaction not covered by one or more of groups , e.g. affinity, ligand exchange or chiral chromatography
B01D 15/16 - Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to the conditioning of the fluid carrier
B01D 15/42 - Selective adsorption, e.g. chromatography characterised by the development mode, e.g. by displacement or by elution
5.
SMB process for producing highly pure EPA from fish oil
The present invention provides a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product, from a feed mixture, which process comprises introducing the feed mixture to a simulated or actual moving bed chromatography apparatus having a plurality of linked chromatography columns containing, as eluent, an aqueous alcohol, wherein the apparatus has a plurality of zones comprising at least a first zone and a second zone, each zone having an extract stream and a raffinate stream from which liquid can be collected from said plurality of linked chromatography columns, and wherein (a) a raffinate stream containing the PUFA product together with more polar components is collected from a column in the first zone and introduced to a nonadjacent column in the second zone, and/or (b) an extract stream containing the PUFA product together with less polar components is collected from a column in the second zone and introduced to a nonadjacent column in the first zone, said PUFA product being separated from different components of the feed mixture in each zone.
The present invention provides a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product from a feed mixture which is a fish oil or which is derived from fish oil, which process comprises the steps of: (i) purifying the feed mixture in a chromatographic separation step, to obtain a first intermediate product; and (ii) purifying the first intermediate product obtained in (i) in a simulated or actual moving bed chromatographic separation step, to obtain a second intermediate product; and (iii) purifying the second intermediate product obtained in (ii) in a simulated or actual moving bed chromatographic separation step, to obtain the PUFA product; wherein an aqueous organic solvent is used as eluent in each separation step; saturated and/or monounsaturated fatty acids present in the feed mixture are removed in the first separation step; the PUFA product is separated from different components of the feed mixture in steps (ii) and (iii); and the PUFA product obtained in the third separation step contains EPA or an EPA derivative in an amount greater than 90 wt %.
The present invention provides a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product from a feed mixture, which comprises: (a) purifying the feed mixture in a first chromatographic separation step using as eluent a mixture of water and a first organic solvent, to obtain an intermediate product; and (b) purifying the intermediate product in a second chromatographic separation step using as eluent a mixture of water and a second organic solvent, to obtain the PUFA product, wherein the second organic solvent is different from the first organic solvent and has a polarity index which differs from the polarity index of the first organic solvent by between 0.1 and 2.0, wherein the PUFA product is other than alpha-linolenic acid (ALA), gamma-linolenic acid (GLA), linoleic acid, an ALA mono- di- or triglyceride, a GLA mono- di- or triglyceride, a linoleic acid mono, di- or triglyceride, an ALA C1 -C4 alkyl ester, a GLA C1 -C4 alkyl ester or a linoleic acid C1 -C4 or a mixture thereof.
The present invention provides a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product from a feed mixture, which process comprises the steps of: (i) purifying the feed mixture in a first separation step in a simulated or actual moving bed chromatography apparatus having a plurality of linked chromatography columns containing, as eluent, an aqueous organic solvent, to obtain an intermediate product; and (ii) purifying the intermediate product obtained in (i) in a second separation step using a simulated or actual moving bed chromatography apparatus having a plurality of linked chromatography columns containing, as eluent, an aqueous organic solvent, to obtain the PUFA product; wherein (a) the first and second separation steps are carried out sequentially on the same chromatography apparatus, the intermediate product being recovered between the first and second separation steps and the process conditions in the chromatography apparatus being adjusted between the first and second separation steps such that the PUFA product is separated from different components of the feed mixture in each separation step; or (b) the first and second separation steps are carried out on separate first and second chromatography apparatuses respectively, the intermediate product obtained from the first separation step being introduced into the second chromatography apparatus, and the PUFA product being separated from different components of the feed mixture in each separation step.
The present invention provides a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product from a feed mixture, which comprises: • (a) purifying the feed mixture in a first chromatographic separation step using as eluent a mixture of water and a first organic solvent, to obtain an intermediate product; and • (b) purifying the intermediate product in a second chromatographic separation step using as eluent a mixture of water and a second organic solvent, to obtain the PUFA product, wherein the second organic solvent is different from the first organic solvent and has a polarity index which differs from the polarity index of the first organic solvent by between 0.1 and 2.0, wherein the PUFA product is other than alpha-linolenic acid (ALA), gamma-linolenic acid (GLA), linoleic acid, an ALA mono- di- or triglyceride, a GLA mono- di- or triglyceride, a linoleic acid mono, di- or triglyceride, an ALA C1 -C4 alkyl ester, a GLA C1 -C4 alkyl ester or a linoleic acid C1 -C4 or a mixture thereof.
The present invention provides a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product, from a feed mixture, which process comprises introducing the feed mixture to a simulated or actual moving bed chromatography apparatus having a plurality of linked chromatography columns containing, as eluent, an aqueous organic solvent, wherein the apparatus has a plurality of zones comprising at least a first zone and second zone, each zone having an extract stream and a raffinate stream from which liquid can be collected from said plurality of linked chromatography columns, and wherein (a) a raffinate stream containing the PUFA product together with more polar components is collected from a column in the first zone and introduced to a nonadjacent column in the second zone, and/or (b) an extract stream containing the PUFA product together with less polar components is collected from a column in the second zone and introduced to a nonadjacent column in the first zone, said PUFA product being separated from different components of the feed mixture in each zone, and wherein the aqueous organic solvent is other than aqueous alcohol.
The present invention provides a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product from a feed mixture, which process comprises the steps of: (i) purifying the feed mixture in a first separation step in a simulated or actual moving bed chromatography apparatus having a plurality of linked chromatography columns containing, as eluent, an aqueous organic solvent, to obtain an intermediate product; and (ii) purifying the intermediate product obtained in (i) in a second separation step using a simulated or actual moving bed chromatography apparatus having a plurality of linked chromatography columns containing, as eluent, an aqueous organic solvent, to obtain the PUFA product; wherein (a) the first and second separation steps are carried out sequentially on the same chromatography apparatus, the intermediate product being recovered between the first and second separation steps and the process conditions in the chromatography apparatus being adjusted between the first and second separation steps such that the PUFA product is separated from different components of the feed mixture in each separation step; or (b) the first and second separation steps are carried out on separate first and second chromatography apparatuses respectively, the intermediate product obtained from the first separation step being introduced into the second chromatography apparatus, and the PUFA product being separated from different components of the feed mixture in each separation step.
The present invention provides a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product from a feed mixture, which process comprises passing the feed mixture through one or more chromatographic columns containing, as eluent, an aqueous organic solvent, wherein the temperature of at least one of the chromatographic columns through which the feed mixture is passed is greater than room temperature.
B01D 15/18 - Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns
B01D 15/38 - Selective adsorption, e.g. chromatography characterised by the separation mechanism involving specific interaction not covered by one or more of groups , e.g. affinity, ligand exchange or chiral chromatography
The present invention provides a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product from a feed mixture which is a fish oil or which is derived from fish oil, which process comprises the steps of: (i) purifying the feed mixture in a chromatographic separation step, to obtain a first intermediate product; and (ii) purifying the first intermediate product obtained in (i) in a simulated or actual moving bed chromatographic separation step, to obtain a second intermediate product; and (iii) purifying the second intermediate product obtained in (ii) in a simulated or actual moving bed chromatographic separation step, to obtain the PUFA product; wherein an aqueous organic solvent is used as eluent in each separation step; saturated and/or monounsaturated fatty acids present in the feed mixture are removed in the first separation step; the PUFA product is separated from different components of the feed mixture in steps (ii) and (iii); and the PUFA product obtained in the third separation step contains EPA or an EPA derivative in an amount greater than 90 wt%.
The present invention provides a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product from a feed mixture, which process comprises the steps of: (i) purifying the feed mixture in a first separation step in a simulated or actual moving bed chromatography apparatus having a plurality of linked chromatography columns containing, as eluent, an aqueous organic solvent, to obtain an intermediate product; and (ii) purifying the intermediate product obtained in (i) in a second separation step using a simulated or actual moving bed chromatography apparatus having a plurality of linked chromatography columns containing, as eluent, an aqueous organic solvent, to obtain the PUFA product; wherein (a) the first and second separation steps are carried out sequentially on the same chromatography apparatus, the intermediate product being recovered between the first and second separation steps and the process conditions in the chromatography apparatus being adjusted between the first and second separation steps such that the PUFA product is separated from different components of the feed mixture in each separation step; or (b) the first and second separation steps are carried out on separate first and second chromatography apparatuses respectively, the intermediate product obtained from the first separation step being introduced into the second chromatography apparatus, and the PUFA product being separated from different components of the feed mixture in each separation step.
The present invention provides a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product from a feed mixture, which process comprises the steps of: (i) purifying the feed mixture in a first separation step in a simulated or actual moving bed chromatography apparatus having a plurality of linked chromatography columns containing, as eluent, an aqueous organic solvent, to obtain an intermediate product; and (ii) purifying the intermediate product obtained in (i) in a second separation step using a simulated or actual moving bed chromatography apparatus having a plurality of linked chromatography columns containing, as eluent, an aqueous organic solvent, to obtain the PUFA product; wherein (a) the first and second separation steps are carried out sequentially on the same chromatography apparatus, the intermediate product being recovered between the first and second separation steps and the process conditions in the chromatography apparatus being adjusted between the first and second separation steps such that the PUFA product is separated from different components of the feed mixture in each separation step; or (b) the first and second separation steps are carried out on separate first and second chromatography apparatuses respectively, the intermediate product obtained from the first separation step being introduced into the second chromatography apparatus, and the PUFA product being separated from different components of the feed mixture in each separation step.
The present invention provides a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product from a feed mixture, which process comprises the steps of: (i) purifying the feed mixture in a first separation step in a simulated or actual moving bed chromatography apparatus having a plurality of linked chromatography columns containing, as eluent, an aqueous organic solvent, to obtain an intermediate product; and (ii) purifying the intermediate product obtained in (i) in a second separation step using a simulated or actual moving bed chromatography apparatus having a plurality of linked chromatography columns containing, as eluent, an aqueous organic solvent, to obtain the PUFA product; wherein (a) the first and second separation steps are carried out sequentially on the same chromatography apparatus, the intermediate product being recovered between the first and second separation steps and the process conditions in the chromatography apparatus being adjusted between the first and second separation steps such that the PUFA product is separated from different components of the feed mixture in each separation step; or (b) the first and second separation steps are carried out on separate first and second chromatography apparatuses respectively, the intermediate product obtained from the first separation step being introduced into the second chromatography apparatus, and the PUFA product being separated from different components of the feed mixture in each separation step.
The present invention provides a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product, from a feed mixture, which process comprises introducing the feed mixture to a simulated or actual moving bed chromatography apparatus having a plurality of linked chromatography columns containing, as eluent, an aqueous organic solvent, wherein the apparatus has a plurality of zones comprising at least a first zone and second zone, each zone having an extract stream and a raffinate stream from which liquid can be collected from said plurality of linked chromatography columns, and wherein (a) a raffinate stream containing the PUFA product together with more polar components is collected from a column in the first zone and introduced to a nonadjacent column in the second zone, and/or (b) an extract stream containing the PUFA product together with less polar components is collected from a column in the second zone and introduced to a nonadjacent column in the first zone, said PUFA product being separated from different components of the feed mixture in each zone, and wherein the aqueous organic solvent is other than aqueous alcohol.
The present invention provides a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product from a feed mixture, which process comprises passing the feed mixture through one or more chromatographic columns containing, as eluent, an aqueous organic solvent, wherein the temperature of at least one of the chromatographic columns through which the feed mixture is passed is greater than room temperature.
B01D 15/18 - Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns
B01D 15/38 - Selective adsorption, e.g. chromatography characterised by the separation mechanism involving specific interaction not covered by one or more of groups , e.g. affinity, ligand exchange or chiral chromatography
C11B 3/10 - Refining fats or fatty oils by adsorption
C11C 1/00 - Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
The present invention provides a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product from a feed mixture, which process comprises the steps of: (i) purifying the feed mixture in a first separation step in a simulated or actual moving bed chromatography apparatus having a plurality of linked chromatography columns containing, as eluent, an aqueous organic solvent, to obtain an intermediate product; and (ii) purifying the intermediate product obtained in (i) in a second separation step using a simulated or actual moving bed chromatography apparatus having a plurality of linked chromatography columns containing, as eluent, an aqueous organic solvent, to obtain the PUFA product; wherein (a) the first and second separation steps are carried out sequentially on the same chromatography apparatus, the intermediate product being recovered between the first and second separation steps and the process conditions in the chromatography apparatus being adjusted between the first and second separation steps such that the PUFA product is separated from different components of the feed mixture in each separation step; or (b) the first and second separation steps are carried out on separate first and second chromatography apparatuses respectively, the intermediate product obtained from the first separation step being introduced into the second chromatography apparatus, and the PUFA product being separated from different components of the feed mixture in each separation step.
The present invention provides a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product, from a feed mixture, which process comprises introducing the feed mixture to a simulated or actual moving bed chromatography apparatus having a plurality of linked chromatography columns containing, as eluent, an aqueous organic solvent, wherein the apparatus has a plurality of zones comprising at least a first zone and second zone, each zone having an extract stream and a raffinate stream from which liquid can be collected from said plurality of linked chromatography columns, and wherein (a) a raffinate stream containing the PUFA product together with more polar components is collected from a column in the first zone and introduced to a nonadjacent column in the second zone, and/or (b) an extract stream containing the PUFA product together with less polar components is collected from a column in the second zone and introduced to a nonadjacent column in the first zone, said PUFA product being separated from different components of the feed mixture in each zone, and wherein the aqueous organic solvent is other than aqueous alcohol.
The present invention provides a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product from a feed mixture, which process comprises passing the feed mixture through one or more chromatographic columns containing, as eluent, an aqueous organic solvent, wherein the temperature of at least one of the chromatographic columns through which the feed mixture is passed is greater than room temperature.
B01D 15/18 - Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns
B01D 15/38 - Selective adsorption, e.g. chromatography characterised by the separation mechanism involving specific interaction not covered by one or more of groups , e.g. affinity, ligand exchange or chiral chromatography
C11B 3/10 - Refining fats or fatty oils by adsorption
C11C 1/00 - Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
The present invention provides a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product from a feed mixture which is a fish oil or which is derived from fish oil, which process comprises the steps of: (i) purifying the feed mixture in a chromatographic separation step, to obtain a first intermediate product; and (ii) purifying the first intermediate product obtained in (i) in a simulated or actual moving bed chromatographic separation step, to obtain a second intermediate product; and (iii) purifying the second intermediate product obtained in (ii) in a simulated or actual moving bed chromatographic separation step, to obtain the PUFA product; wherein an aqueous organic solvent is used as eluent in each separation step; saturated and/or monounsaturated fatty acids present in the feed mixture are removed in the first separation step; the PUFA product is separated from different components of the feed mixture in steps (ii) and (iii); and the PUFA product obtained in the third separation step contains EPA or an EPA derivative in an amount greater than 90 wt%.
The present invention provides a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product, from a feed mixture, which process comprises introducing the feed mixture to a simulated or actual moving bed chromatography apparatus having a plurality of linked chromatography columns containing, as eluent, an aqueous alcohol, wherein the apparatus has a plurality of zones comprising at least a first zone and second zone, each zone having an extract stream and a raffinate stream from which liquid can be collected from said plurality of linked chromatography columns, and wherein (a) a raffinate stream containing the PUFA product together with more polar components is collected from a column in the first zone and introduced to a nonadjacent column in the second zone, and/or (b) an extract stream containing the PUFA product together with less polar components is collected from a column in the second zone and introduced to a nonadjacent column in the first zone, said PUFA product being separated from different components of the feed mixture in each zone.
There is provided a process for purifying a fatty acid, which process comprises reacting a fatty acid with a lithium salt in a first solution and under conditions to allow formation of a precipitate of a lithium salt of the fatty acid; isolating the precipitate; dissolving the precipitate in a second solution followed by separation of the organic and aqueous layers so formed; and evaporating the organic layer to isolate the purified fatty acid. There is also provided a process for increasing the length of a fatty acid, and the use of a lithium salt to purify a fatty acid.
A composition comprising a polyunsaturated fatty acid (PUFA) product is provided. The PUFA product is recovered from a feed mixture by a chromatographic separation process. The process includes introducing the feed mixture to a simulated or actual moving bed chromatography apparatus having a plurality of linked chromatography columns. The apparatus has a plurality of zones including a first zone and a second zone, each zone having an extract stream and a raffinate stream. The raffinate stream containing the PUFA product together with more polar components is collected from a column in the first zone and introduced to a nonadjacent column in the second zone. The extract stream containing the PUFA product together with less polar components is collected from a column in the second zone and introduced to a nonadjacent column in the first zone. The PUFA product is separated from different components of the feed mixture in each zone.
The present invention provides a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product, from a feed mixture, which process comprises introducing the feed mixture to a simulated or actual moving bed chromatography apparatus having a plurality of linked chromatography columns containing, as eluent, an aqueous alcohol, wherein the apparatus has a plurality of zones comprising at least a first zone and second zone, each zone having an extract stream and a raffinate stream from which liquid can be collected from said plurality of linked chromatography columns, and wherein (a) a raffinate stream containing the PUFA product together with more polar components is collected from a column in the first zone and introduced to a nonadjacent column in the second zone, and/or (b) an extract stream containing the PUFA product together with less polar components is collected from a column in the second zone and introduced to a nonadjacent column in the first zone, said PUFA product being separated from different components of the feed mixture in each zone.
A composition having a polyunsaturated fatty acid (PUFA) product is provided. The composition has an amount of isomeric impurities up to 1 wt% and has greater than 85 wt% PUFA product. The PUFA product is docosahexaenoic acid.
A61K 31/202 - Carboxylic acids, e.g. valproic acid having a carboxyl group bound to an acyclic chain of seven or more carbon atoms, e.g. stearic, palmitic or arachidic acid having three or more double bonds, e.g. linolenic acid
B01D 15/10 - Selective adsorption, e.g. chromatography characterised by constructional or operational features
B01J 8/08 - Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with moving particles
30.
SIMULATED MOVING BED CHROMATOGRAPHIC SEPARATION PROCESS FOR THE PURIFICATION OF POLYUNSATURATED FATTY ACIDS
The present invention provides a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product, from a feed mixture, which process comprises introducing the feed mixture to a simulated or actual moving bed chromatography apparatus having a plurality of linked chromatography columns containing, as eluent, an aqueous alcohol, wherein the apparatus has a plurality of zones comprising at least a first zone and second zone, each zone having an extract stream and a raffinate stream from which liquid can be collected from said plurality of linked chromatography columns, and wherein (a) a raffinate stream containing the PUFA product together with more polar components is collected from a column in the first zone and introduced to a nonadjacent column in the second zone, and/or (b) an extract stream containing the PUFA product together with less polar components is collected from a column in the second zone and introduced to a nonadjacent column in the first zone, said PUFA product being separated from different components of the feed mixture in each zone.
B01D 15/18 - Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns
C07C 51/487 - Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
C11B 3/10 - Refining fats or fatty oils by adsorption
C12P 7/64 - Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
03 - Cosmetics and toiletries; cleaning, bleaching, polishing and abrasive preparations
05 - Pharmaceutical, veterinary and sanitary products
40 - Treatment of materials; recycling, air and water treatment,
Goods & Services
[ essential oils, non-medicated oils for cosmetic use and further manufacture of cosmetic products, cosmetics, and distilled oils for body care, all foregoing comprised substantially of omega oils ] [ medicated oils, ] omega oils for pharmaceutical purposes, [ and edible fish oils for medical purposes, ] all the foregoing comprised substantially of omega oils [ processing of oils ]
03 - Cosmetics and toiletries; cleaning, bleaching, polishing and abrasive preparations
05 - Pharmaceutical, veterinary and sanitary products
29 - Meat, dairy products, prepared or preserved foods
40 - Treatment of materials; recycling, air and water treatment,
Goods & Services
(1) Essential oils, namely, essential oils for cosmetic purposes, essential oils for personal use, essential oils for the care of the body, essential oils for the care of the skin, essential oils for the care of the hair, essential oils for use in manufacturing skin care preparations, essential oils for use in the manufacturing of perfumes, essential oils for the production of perfumes, essential oils for use in cosmetics, essential oils for use in manufacturing cosmetics, essential oils used in the preparation of cosmetics; non-medicated oils namely omega oils that are not impregnated with medicine; cosmetics; medicated oils namely omega oils that are impregnated with medicine; omega oils for use in the manufacture of pharmaceutical products; edible fish oils; distilled oils for body care namely, distilled oils for personal use, distilled oils for the care of the skin, distilled oils for use in manufacturing skin care preparations.
(2) Edible oils. (1) Processing of omega oils namely chromatographic separation of the same for the production of omega oil concentrate.
