WO2001007137A1 - Säulenchromatographisches trennverfahren - Google Patents
Säulenchromatographisches trennverfahren Download PDFInfo
- Publication number
- WO2001007137A1 WO2001007137A1 PCT/EP2000/006853 EP0006853W WO0107137A1 WO 2001007137 A1 WO2001007137 A1 WO 2001007137A1 EP 0006853 W EP0006853 W EP 0006853W WO 0107137 A1 WO0107137 A1 WO 0107137A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- liquid
- column
- eluent
- phase
- bar
- Prior art date
Links
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
- B01D15/40—Selective adsorption, e.g. chromatography characterised by the separation mechanism using supercritical fluid as mobile phase or eluent
-
- 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
- B01D15/42—Selective adsorption, e.g. chromatography characterised by the development mode, e.g. by displacement or by elution
- B01D15/424—Elution mode
- B01D15/426—Specific type of solvent
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
-
- 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
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
- C11B7/0008—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents
- C11B7/005—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents in solvents used at superatmospheric pressures
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/26—Conditioning of the fluid carrier; Flow patterns
- G01N30/38—Flow patterns
- G01N30/46—Flow patterns using more than one column
- G01N30/468—Flow patterns using more than one column involving switching between different column configurations
Definitions
- the present invention relates to a column chromatography separation process using a liquid and low molecular weight fluid as an eluent for the isolation and / or purification and / or preparative extraction of (natural) substances from mixtures of substances, preferably mixtures of natural substances.
- HPLC takes advantage of the knowledge that the separation performance of a column increases with decreasing grain size of the stationary phase. HPLC uses a much finer chromatographic separation material (3-10 ⁇ m) than that of
- the necessary pumps can be operated in analytical HPLC up to a pressure of 400 bar.
- pumps are operated up to a pressure of 70 (pump output: 300 l / h) to 100 bar (pump output: 60 l / h eluent (liquid)) (see e.g. Merck, Chrombook, p. 233, 1996, Darmstadt).
- the limiting factor in HPLC, especially with high flows, is the pump pressure.
- the column lengths used are therefore mostly short; the following applies: the smaller the particle diameter of the chromatographic material used, the shorter the columns have to be. In principle, compensation can be made by means of higher maximum working pressures, but this increases the operating costs enormously and can lead to the inefficiency of the HPLC method in the context of a preparative application.
- SFC has established itself as a column chromatography separation process with gases (CO 2 , N 2 O, SF 6 etc.) in the supercritical state as the mobile phase.
- gases CO 2 , N 2 O, SF 6 etc.
- liquids and gases are heated under pressure, which are converted into the supercritical state above the respective critical temperature and the critical pressure.
- supercritical fluids are not only distinguished by real fluids by their lower density, much lower viscosity and much higher diffusion coefficients, but above all by their excellent solvency. This is why supercritical liquids made of CO 2 , ethylene, propane, ammonia, nitrous oxide, water, Toluene, nitrogen heterocycles and others.
- SFE supercritical fluid extraction
- SCFE also called "destruction"
- the SFC works at temperatures above 35 ° C and a pressure on the column outlet side of over 120 bar.
- Verillon and Coleman describe on page 64 (Anton supra) the temperature and pressure range for working with fluids such as CO 2 - between 3 to 200 ° C and 90 - 400 bar.
- the separations take place in the supercritical and subcritical range, but not in the liquid range, ie in a pressure range below the critical pressure and temperature.
- Jusforques describes on p. 409 in Chap. 14 (supra Anton) the required working range with temperatures between 0 and 150 ° C and pressures between 100 and 350 bar (SFC equipment: Super C12 in the context of the preparative SFC). Prochrom also specifies a working pressure range between 100 and 350 bar, at temperatures between 10 and 80 ° C (Prochrom, prospectus for semi-preparative Supercritical Fluid Chromatograph, type: SuperC 20, 1998, Chamigneulle, France).
- EP 0 099 765 B1 discloses that the inlet pressure of the mixture into the column must be greater than the critical pressure of the eluent, namely between 1.05 and 3. Pressures less than the critical pressure are expressly described as separation conditions.
- Perrut describes in NO 163139 as separation conditions only the supercritical and subcritical range, namely pressures of 70-250 bar and temperatures between 25 and 80 ° C.
- the present invention is therefore based on the object of providing a column chromatography process in the context of liquid chromatography for the industrial isolation and / or purification and / or preparative extraction of (natural) substances from (natural) substance mixtures, which leads to pure products due to a high separation performance ,
- the present invention thus relates to a process for column-chromatographic separation of mixtures of substances, a fluid or an eluent being used Mixing of fluids in liquid, non-subcritical and non-critical state is used, which are gaseous at 25 ° C and 1 bar (hereinafter the inventive method).
- the eluents used according to the invention are low-molecular compounds which are gaseous under normal conditions (25 ° C.; 1 bar) and which are used under such temperature and pressure conditions that they are not in the critical state or in the liquid state or not in the subcritical state (i.e. not above the critical temperature and below the critical pressure).
- Preferred eluents for the process according to the invention are volatile compounds with little interaction
- eluents are liquid nitrous oxide (N 2 0); Liquid fluorocarbons or fluorocarbons ("freons"), such as chlorotrifluoromethane (CCIF 3 ), trifluoromethane (CHF 3 ), tetrafluoromethane (CF 4 ), 1, 1, 1, 2-tetrafluoroethane (CF 4 H 2 ), liquid carbon dioxide (C0 2 ), liquid sulfur hexafluoride (SF 6 ), liquid propene (C 3 H 6 ), liquid propane (C 3 H 8 ), liquid ammonia (NH 3 ), liquid sulfur dioxide (SO 2 ), liquid xenon (Xe), liquid ethane ( C 2 H 6 ), which are gaseous under normal conditions.
- CCIF 3 chlorotrifluoromethane
- CHF 3 trifluoromethane
- CF 4 tetrafluoromethane
- CF 4 H 2 1, 1, 1, 2-tetrafluoroethane
- Eluents are preferably used which have a dynamic viscosity of 10 "4 - 10 " 6 Pa s, preferably 2 * 10 * 4 - 2 * 10 "6 Pa s, a density of 0.5 - 1, 2 g / ml, preferably 0.5-1.2 g / ml.
- the dynamic viscosity is measured for the purposes of this application with a capillary viscometer at 25 ° C.
- such lower molecules are in liquid form as eluents in the mobile phase.
- Eluents which are known to the person skilled in the field of SFC are preferably used.
- liquid carbon dioxide is very particularly preferred, specifically in the liquid temperature range from -57 ° C. to 31.3 ° C., preferably from 0 to 20 ° C.
- liquid carbon dioxide is very particularly preferred, specifically in the pressure range of greater than 30 bar, preferably 30 to 150 bar and very preferably 30 to 60 bar.
- the liquid pressure range of the carbon dioxide is 5.2 to 73.7 bar.
- the critical pressure is 73.7 bar and the critical temperature is 31.3 ° C.
- the triple point of carbon dioxide is -57 ° C and 5.2 bar.
- the working range of the low molecular weight eluent used is the liquid phase with the associated p, T values.
- chromatographic separation in the sense of this invention means that a separation of substances takes place by distribution, that is to say by the dissolving process in both immiscible phases and by adsorption on a solid (adsorbent) on a stationary phase in the presence of an eluent as the mobile phase.
- LSC liquid-solid chromatography
- IUPAC has proposed terminology for the terms used here, which is expressly referred to.
- the mobile phase containing an eluent is mixed with the aid of a modifier customary in chromatography, such as an alcohol which is liquid under operating conditions, for example ethanol or methanol.
- This modifier can optionally be mixed with other auxiliaries and additives, such as acids or bases (eg acetic acid or diethylamine).
- the method according to the invention can be used for column lengths in a wide range.
- the columns are usually at least 10 cm long, but lengths of 0.25-2.0 m are preferred, and 1.1-1.7 m are particularly preferred.
- the pressure drop can be estimated according to Formula 1 on Table 1. Since the viscosity of the liquid eluents used is small, the resulting pressure drop is also low. Due to the low pressure drop per cm column, the column can be chosen to be correspondingly long with the same particle diameter of the stationary phase or, compared to HPLC, smaller particle diameters can be used with a constant column length.
- the method according to the invention can be operated with conventional arrangements, such as are also used in the known SFC methods.
- C0 2 is cooled from a liquid C0 2 -Vorratstank by means of a heat exchanger.
- the delivered by the pump C0 2 is brought by means of the heat exchanger to supercritical conditions (T> 31 ° C, p> 74bar), typically 40-60 c C. That CO 2 flows through the separation column and is expanded to a pressure control valve.
- This pressure regulating valve regulates the column outlet pressure, which prevails at the end of the separation column and is kept above the critical pressure (p> 74bar). This ensures supercritical separation conditions in the separation column.
- the C0 2 cools down due to the adiabatic expansion at the pressure control valve.
- the CO 2 is then heated with a heat exchanger and brought into the gaseous state.
- the product is separated from the gaseous C0 2 in a separator.
- the gaseous C0 2 reaches the storage tank via the heat exchanger, which liquefies it again.
- the result is a closed C0 2 cycle.
- the product is injected discontinuously from the storage vessel with the help of the pump onto the separation column.
- a total of at least four heat exchangers are required in an energy-intensive manner.
- the particular advantage of the method according to the invention is that an energy-consuming alternating cooling and heating of the C0 2 is avoided.
- Einzuspeisendes C0 2 is cooled from a liquid C0 2 -Vorratstank by means of a heat exchanger.
- the pumped C0 2 is set to the separation temperature by means of the heat exchanger. However, this can be very small since the C0 2 is only heated from typically 0-5 ° C to 5-20 ° C.
- this heat exchanger can also be taken out of operation.
- the liquid CO 2 flows through the separation column.
- the individual fractions are diverted to so-called fractionation columns, for example to three fractionation columns. Any number of fractionation columns are possible, but in the simplest case a fractionation column and an additional pipeline, which connects the changeover valve with another changeover valve.
- the column outlet pressure is controlled with a pressure control valve.
- the expansion of the CO 2 takes place at this valve.
- the sample is separated on the separation column.
- the changeover valve is switched so that CO and component A are diverted in the direction of the further changeover valve.
- the liquid C0 2 is relaxed.
- the C0 2 loses its solvent power.
- Component A is thereby retained on the fractionation column.
- the C0 2 is further cooled by a heat exchanger (if necessary) and is returned to the storage tank.
- the changeover valve is switched to another fractionation column.
- the eluting component B is held on this fractionation column.
- Component C on another fractionation column. If no sample substance elutes, the C0 2 flow can either be conducted via one of the fractionation columns or an additional pipeline with a pressure control valve, which connects the switching valve with the other switching valve.
- the chromatographic material of the separation column is chosen so that the resolution of the sample components is maximum.
- the material of the fractionation columns is selected so that adsorption of the respective sample component is maximal under the conditions prevailing there during the separation.
- This procedure can be repeated for several injections (until the capacity of a fractionation column is reached).
- the respective components are eluted with a suitable strong solvent, e.g. Ethanol.
- a separate pump conveys the eluent via the changeover valve to the outlet after the other changeover valve. In this case, the value fractions are collected dissolved in liquid.
- the pressure control valve can be fitted directly behind the separation column.
- the expanded C0 2 with the respective sample component is only passed to the relevant fractionation column after the expansion by means of the changeover valve.
- the pressure control valves can be arranged behind the fractionation columns. additionally there are additional separators behind it.
- the pressure behind the fractionation column is regulated.
- the material of the fractionation columns is chosen so that components A, B and C are retained in the relevant fractionation column under the prevailing conditions.
- the individual components of a modifier can be separated for the elution and the respective separators from CO 2 by increasing the elution strength of the CO 2 and / or additive.
- the elution can also be carried out with a liquid eluent.
- the separators can be omitted.
- the arrangement can also be modified so that only one separator behind the changeover valve is used instead of three separators.
- a conventional SFC system can be operated much more economically in terms of energy by the method according to the invention.
- the C0 2 does not need to be heated at all or only slightly. Due to the lower pressure upstream of the pressure control unit, the cooling due to the adiabatic expansion is also less and therefore much less energy has to be supplied to the heat exchanger after the separation column.
- the method according to the invention can be carried out on any SFC system.
- the process according to the invention is very particularly suitable for the column-chromatographic separation of unsaturated, in particular polyunsaturated, higher fatty acids or their derivatives, such as esters or lipids, preferably from natural oils, such as vegetable oil, algae oil, oil from microorganisms or fungi, and also fish oil, and thus for extraction and Purification of SDA (steahdonic acid, 18: 4, n3), AA (arachidonic acid, 20: 4, n-6), ETA (eicosatetraenoic acid, 20: 4, n-3), EPA 25 (eicosapentaenoic acid, 20: 5, n-3), DPA (docosapentaenoic acid, 22: 5, n-3), DHA (docosahexaenoic acid, 22: 6, n-3).
- GLA gamma-oleolenic acid 18: 3, n-6
- ALA alpha-linolenic acid 18: 3, n-3
- DPA docos
- Table 2 shows the EPA content in% of the respective fraction. As can easily be seen, the course is very similar. However, the separation in the liquid area of the invention was much faster.
- Table 3 shows the purities of the fractions on both EPA and DHA for the same separations. It can also be seen here that the separations are comparable, but the separation in the liquid region can be carried out in half the time with this phase.
- Tables 4 and 5 show a separation of the same starting material on a different stationary phase. It can also be seen here that the separations are very similar under different conditions. In this stationary phase, however, the substances later elute under liquid conditions. The maximum achievable EPA purity is approx. 80% on this stationary phase. If an EPA purity of more than 70% is defined as a comparison for the mass yield, the yield of 36.2% in liquid conditions is significantly higher than that of supercritical conditions with only 30.3%. The pronounced tailing of both the EPA and the DHA is probably due to highly active silanol groups. This phase is less suitable for the separation. However, it could be shown that the separations are comparable in different state areas.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Wood Science & Technology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Extraction Or Liquid Replacement (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU68242/00A AU6824200A (en) | 1999-07-21 | 2000-07-18 | Column chromatography separation method |
EP00956199A EP1202785B1 (de) | 1999-07-21 | 2000-07-18 | Säulenchromatographisches trennverfahren |
AT00956199T ATE240142T1 (de) | 1999-07-21 | 2000-07-18 | Säulenchromatographisches trennverfahren |
DE50002204T DE50002204D1 (de) | 1999-07-21 | 2000-07-18 | Säulenchromatographisches trennverfahren |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19934168A DE19934168A1 (de) | 1999-07-21 | 1999-07-21 | Säulenchromatographisches Trennverfahren im Rahmen einer Flüssigkeitschromatographie mittels niedermolekularen Eluenten |
DE19934168.0 | 1999-07-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001007137A1 true WO2001007137A1 (de) | 2001-02-01 |
Family
ID=7915526
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2000/006853 WO2001007137A1 (de) | 1999-07-21 | 2000-07-18 | Säulenchromatographisches trennverfahren |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP1202785B1 (de) |
AT (1) | ATE240142T1 (de) |
AU (1) | AU6824200A (de) |
DE (2) | DE19934168A1 (de) |
ES (1) | ES2199849T3 (de) |
WO (1) | WO2001007137A1 (de) |
ZA (1) | ZA200200426B (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108152393A (zh) * | 2017-12-08 | 2018-06-12 | 国网陕西省电力公司电力科学研究院 | 1100kV滤波器用柱式断路器中四氟化碳的检测方法 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
LU500141B1 (de) | 2021-05-10 | 2022-11-10 | K D Pharma Bexbach Gmbh | Chromatographieverfahren und -vorrichtung, insbesondere Verfahren und Vorrichtung zur superkritischen Flüssigkeitschromatographie |
US20240219356A1 (en) | 2021-05-10 | 2024-07-04 | K.D. Pharma Bexbach Gmbh | Chromatography method and device, in particular method and device for supercritical liquid chromatography |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0127926A1 (de) * | 1983-06-03 | 1984-12-12 | Hewlett-Packard Company | Chromatographische Trennung |
US5422007A (en) * | 1992-04-29 | 1995-06-06 | Institut Francais Du Petrole & Separex | Method and apparatus for fractionation of a mixture on a simulated fluidized bed in the presence of a compressed gas, a supercritical fluid or a subcritical liquid |
-
1999
- 1999-07-21 DE DE19934168A patent/DE19934168A1/de not_active Withdrawn
-
2000
- 2000-07-18 DE DE50002204T patent/DE50002204D1/de not_active Expired - Lifetime
- 2000-07-18 EP EP00956199A patent/EP1202785B1/de not_active Expired - Lifetime
- 2000-07-18 AU AU68242/00A patent/AU6824200A/en not_active Abandoned
- 2000-07-18 WO PCT/EP2000/006853 patent/WO2001007137A1/de active IP Right Grant
- 2000-07-18 AT AT00956199T patent/ATE240142T1/de active
- 2000-07-18 ES ES00956199T patent/ES2199849T3/es not_active Expired - Lifetime
-
2002
- 2002-01-17 ZA ZA200200426A patent/ZA200200426B/en unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0127926A1 (de) * | 1983-06-03 | 1984-12-12 | Hewlett-Packard Company | Chromatographische Trennung |
US5422007A (en) * | 1992-04-29 | 1995-06-06 | Institut Francais Du Petrole & Separex | Method and apparatus for fractionation of a mixture on a simulated fluidized bed in the presence of a compressed gas, a supercritical fluid or a subcritical liquid |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108152393A (zh) * | 2017-12-08 | 2018-06-12 | 国网陕西省电力公司电力科学研究院 | 1100kV滤波器用柱式断路器中四氟化碳的检测方法 |
Also Published As
Publication number | Publication date |
---|---|
EP1202785A1 (de) | 2002-05-08 |
ES2199849T3 (es) | 2004-03-01 |
DE19934168A1 (de) | 2001-01-25 |
AU6824200A (en) | 2001-02-13 |
ATE240142T1 (de) | 2003-05-15 |
EP1202785B1 (de) | 2003-05-14 |
ZA200200426B (en) | 2003-05-28 |
DE50002204D1 (de) | 2003-06-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE69401506T2 (de) | Verfahren zur chromatografischer fraktionierung von fettsäuren und ihre derivaten | |
DE69020825T2 (de) | Kontinuierliches Verfahren und Vorrichtung für eine chromatographische Trennung einer Mischung von mindestens drei Bestandteilen in drei gereinigte Ausflüsse mittels eines Lösungsmittels bei zwei verschiedenen Temperaturen und/oder Drucken. | |
Salgın | Extraction of jojoba seed oil using supercritical CO2+ ethanol mixture in green and high-tech separation process | |
DE69807449T2 (de) | Reinigung mehrfach ungesättigter fettsäureglyceride | |
DE60218834T2 (de) | Trennung von mischungen aus pflanzenöl-triglyceriden durch festbettadsorption | |
DE69013702T2 (de) | Verfahren zur Extraktion und Abscheidung und Vorrichtung zur Verwendung von überkritischem Druck. | |
Glisic et al. | The combined extraction of sage (Salvia officinalis L.): Ultrasound followed by supercritical CO2 extraction | |
Markom et al. | Supercritical CO2 fractionation of crude palm oil | |
DE60118234T2 (de) | Verfahren zur verminderung der konzentration von unerwünschten bestandteilen in einer zusammensetzung | |
Fang et al. | Separation of natural tocopherols from soybean oil byproduct with supercritical carbon dioxide | |
EP1034160A1 (de) | Verfahren zur herstellung von fettsäuremethylester und anlage zur durchführung des verfahrens | |
HUE025265T2 (en) | Simulated moving bed chromatography method for extracting high purity eicosapentaenoic acid from fish oil | |
DE60033904T2 (de) | Chromatographisches Verfahren zur Isolieren von Squalen, Steroiden, Vitamin E und Carotenoiden. | |
EP3630326A1 (de) | Verfahren zum trennen von naturstoffgemischen mittels scpc | |
US20220008839A1 (en) | Semi-aqueous method for extracting a substance | |
CN107207398A (zh) | 长链二酸的提纯 | |
CN105873893A (zh) | 用于生产多不饱和脂肪酸的色谱法 | |
JP2020090680A (ja) | 高度に精製したポリ不飽和脂肪酸を生成するクロマトグラフプロセス | |
EP1202785B1 (de) | Säulenchromatographisches trennverfahren | |
US6677469B1 (en) | Supercritical fluid fractionation process for phytosterol ester enrichment vegetable oils | |
Chen et al. | Supercritical carbon dioxide extraction of rice bran oil and column partition fractionation of γ-oryzanols | |
Azenha et al. | Enhanced separation of bioactive triterpenic acids with a triacontylsilyl silica gel adsorbent: From impulse and breakthrough experiments to the design of a simulated moving bed unit | |
DE102007061436A1 (de) | Verfahren zur Gewinnung von Fettbegleitstoffen aus Kraftstoffen und Verwendung dieses Verfahrens | |
CN107176909A (zh) | 一种使用超临界流体色谱纯化二十二碳六烯酸的方法 | |
Alkio | Purification of pharmaceuticals and nutraceutical compounds by sub-and supercritical chromatography and extraction |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AL AM AT AU AZ BA BB BG BR BY CA CH CN CR CU CZ DE DK DM EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ UA UG US UZ VN YU ZA ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2000956199 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2002/00426 Country of ref document: ZA Ref document number: 200200426 Country of ref document: ZA |
|
WWP | Wipo information: published in national office |
Ref document number: 2000956199 Country of ref document: EP |
|
REG | Reference to national code |
Ref country code: DE Ref legal event code: 8642 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 10069080 Country of ref document: US |
|
WWG | Wipo information: grant in national office |
Ref document number: 2000956199 Country of ref document: EP |
|
NENP | Non-entry into the national phase |
Ref country code: JP |