EP1171555B1 - Procede pour eliminer des acides gras libres, contenus dans des corps gras et des huiles d'origine biologique ou dans leurs condensats de vapeur - Google Patents

Procede pour eliminer des acides gras libres, contenus dans des corps gras et des huiles d'origine biologique ou dans leurs condensats de vapeur Download PDF

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EP1171555B1
EP1171555B1 EP00922646A EP00922646A EP1171555B1 EP 1171555 B1 EP1171555 B1 EP 1171555B1 EP 00922646 A EP00922646 A EP 00922646A EP 00922646 A EP00922646 A EP 00922646A EP 1171555 B1 EP1171555 B1 EP 1171555B1
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Prior art keywords
fatty acids
weight
free fatty
water
organic nitrogen
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EP1171555A2 (fr
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Siegfried Peter
Eckhard Weidner
Martin Drescher
Wolfgang König
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Peter Siegfried Prof Dr
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Peter Siegfried Prof Dr
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    • 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
    • C11B3/02—Refining fats or fatty oils by chemical reaction
    • C11B3/06—Refining fats or fatty oils by chemical reaction with bases

Definitions

  • the present invention relates to a method of removal free fatty acids from fats and oils of biological origin or their damper condensates by extraction.
  • oils and fats of biological origin serve as raw materials for the production of surfactants, plasticizers, waxes, lubricants, Fatty alcohols, etc.
  • Essential components of fats and Oils are the triesters of glycerides and fatty acids, the so-called Triglycerides.
  • the physical properties of the Fats and oils are a) determined by the chain length of the fatty acids, b) by the degree of saturation of the fatty acids and c) by the Distribution of the different fatty acids over the three hydroxyl groups of glycerin determined. Fats with a high proportion saturated fatty acids are generally at ambient temperature firmly. Fats or oils from predominantly unsaturated fatty acids are liquid at ambient temperature.
  • the fats and oils of biological origin contain a number of by-products, the shelf life, smell, taste and appearance affect.
  • the most important by-products are: suspended matter, organic phosphorus compounds, free fatty acids, Dyes and fragrances. Mucus and other complex Colloidal compounds can cause the hydrolytic breakdown of fats and promote oils in their storage and are in the further Refining disruptive. Therefore, through the process of so-called degumming removed.
  • the degumming is based on hydration with water or direct steam.
  • the organic phosphorus compounds (phosphatides) take part Water, swell and become insoluble.
  • Phosphorus compounds and suspended matter are removed the other task in free fatty acids and color and To separate odors.
  • Commercial raw fats and oils contain on average 1 to 3% by weight of free fatty acids, good ones Varieties 0.5% by weight and less, some palm, olive and Fish oils 20% by weight and more.
  • the one used to remove the free fatty acids Deacidification mainly by treatment with aqueous Alkali solutions or by damping at temperatures of approx. 220 ° C executed.
  • the removal of the free fatty acids by Esterification with glycerin or with a monohydric alcohol, by selective solvent extraction or by adsorbents has less importance. The following are the previously known deacidification processes explained in more detail.
  • So steam deacidification is an alternative has been developed. This also as physical refining or distillative deacidification processes the free fatty acids with hot steam under vacuum also continuously removed from the crude oils.
  • This comes it is not so important that the fatty acids distill off completely because fatty acids can remain in a small amount expediently removed by post-refining with lye become.
  • the crude fat must be removed before the deacidification by distillation however as completely as possible of mucilages, phosphatides and metal traces are freed - usually by the Treatment with phosphoric acid - as the accompanying substances during the Distillation leads to dark, unpleasant tasting substances that can then hardly be removed.
  • the neutralization of oils and fats by separating the free fatty acids from the raw fat by means of selective acting Solvent is another method that is especially useful for highly acidic oils and fats come into question.
  • Solvent allows the liquid extraction with ethanol the deacidification of Olive oil with 22% by weight of free fatty acids down to about 3% by weight free fatty acids.
  • Another extractant which at suitable temperatures only free fatty acids and very strong Unsaturated triglycerides dissolves is furfural.
  • the Selexol process uses liquid propane used as an extractant in countercurrent.
  • the liquid Propane selectively dissolves saturated neutral oil, while fatty acids, Oxidation products, unsaponifiables and the highly unsaturated Glycerides can hardly be dissolved and remain. This method is mainly used for the fractionation of fish oils and Fish liver oils applied.
  • degumming and alkali refining have already become one some brightening, there is generally a decolorization stage switched on.
  • Deodorization is essential steam distillation, in which the volatile compounds be separated from the non-volatile glycerides.
  • the Fragrances and aromas are predominantly aldehydes and Ketones that are characterized by autoxidative or hydrolytic reactions during the processing and storage of fats and oils have formed.
  • the low partial pressure of those to be removed Connections requires that the damping be done in a vacuum becomes. Steaming is usually done at 180 to 220 ° C and a pressure from 6 to 22 mbar.
  • US Patent 2,157,882 also uses extraction instead extraction of free fatty acids with sodium hydroxide solution with a Alkanolamine suggested to be the most free Remove fatty acids and some of the dyes. That so However, treated oil is cloudy and tends to decompose at the time Storage. That is why it is suggested to use the laundry Follow ethanolamine a wash with a dilute sodium hydroxide solution allow. Then the deacidified oil is washed with water, to remove the last traces of alkali.
  • the invention is therefore based on the object of an improved Process for the deacidification of oils and fats biological To indicate origin, on the one hand also high levels of free Can handle fatty acids without technical problems, and on the other hand, the production of very high quality Fats and oils, such as those made possible by the food industry be desired.
  • the method according to the invention is based on the fact that, surprisingly, when deacidifying Oils (or fats) with a high percentage of free fatty acids by means of aqueous solutions of organic bases, for example 2-dimethylamino-ethanol, then does not form a viscous soap stick, if the amine content in the aqueous solution is at least about 20 % By weight and at most about 60% by weight and preferably between is about 30% and about 40% by weight. Instead are under such conditions both the oil phase and the Extract phase liquids with low viscosity. The phase separation runs quickly within a few minutes; the emerging phases are clear.
  • the concentrations of sodium hydroxide in the chemical Corresponding to deacidification, a highly viscous soap stick.
  • the basic nitrogen compound must contain at least about 40 wt .-% water so that in Equilibrium with the oil to be deacidified formed two phases become.
  • the concentration of the organic base, for example of 2-dimethylamino-ethanol, in the aqueous Solution at least about 20 wt .-%, better still about 30 to 40 % By weight, so that no viscous soap stick or cloudy Phases arise.
  • the one used for deacidification aqueous solution according to the invention has a content of about 20 % By weight to about 60% by weight of organic nitrogen compound must have.
  • Residues of the basic nitrogen compounds dissolved in the raffinate are preferably mixed with water or with dilute acetic acid, Lactic acid, citric acid, sulfuric acid or hydrochloric acid solutions washed out.
  • traces of the basic Extractant in the raffinate by stripping with carbon dioxide away.
  • stripping with carbon dioxide occurs simultaneously a drying of the oil.
  • the carbon dioxide can be diluted Gas or as a dense, supercritical gas for disposal from traces of the basic nitrogen compounds used the raffinate can be used.
  • the removal of the extractant used according to the invention can be easily by distillation respectively.
  • the prerequisite is that the vapor pressure of the water is approximately equal to or higher than the vapor pressure of the basic nitrogen compound (s) used.
  • the water and the basic organic compound are distilled off together or the water is first preferably distilled off, where the ratio of basic compound to water is constant remains or increases and the formation of a viscous Soapstocks is avoided.
  • the vapor pressure of the basic Connection higher than water vapor pressure the ratio would decrease from basic connection to water and finally the Form a viscous soap stick.
  • the boiling point of the basic nitrogen compound (s) on the one hand, equal to or higher than the boiling point of the water and on the other hand lower than the boiling point of the extracting fatty acids.
  • Suitable basic, organic compounds for the process according to this invention should have the following properties: a) the compound should, if possible, no amides with the form free fatty acids; b) the connection should be in with water be miscible with any ratio; c) the boiling point of the Connection should be equal to or higher than that of water, d) the odor from the aqueous solutions should be as low as possible.
  • Suitable organic Nitrogen compounds are: N-methylmorpholine, 2-dimethylaminoethanol, 3- (diethylamino) -1-propanol, 2-diethylaminoethanol, 1- (dimethylamino) -2-propanol, dimethylformamide, N-methylmorpholine, 2-methylethylaminoethanol, 2-dibutylaminoethanol, Dimethylformamide, morpholine, 2-diisopropylaminoethanol, etc.
  • tertiary amines are used because of their higher basicity of binary and monosubstituted amines preferred.
  • oils and fats to be deacidified should be degummed and be filtered, especially if more than 100 ppm phosphatide available. Contains the fat or oil prepared in this way still dissolved oxygen, which also before further processing should be removed.
  • the process then involves the deacidification of the starting material while protecting temperature-sensitive connections such as Carotenes, tocotrienols, tocopherols etc. These among others nutritionally important compounds are also included conventional physical refining using direct steam is carried out due to the high temperatures largely destroyed or driven out.
  • the invention is suitable Procedures also excellent for removing the free Fatty acids from the damper condensates of fats and oils by means of the conventional physical just mentioned Refining, i.e. by means of steam deacidification.
  • damper condensates generally contain free fatty acids in very high concentrations, usually around 80 up to 94% by weight. Because of the high content of free fatty acids
  • the extractant used according to the invention i.e. the Mixture of organic base and water, but richer of the basic nitrogen compound than previously related described with the deacidification of fats and oils.
  • the Proportion of organic nitrogen compound in the extractant should be at least about 40% by weight. If such a aqueous solution rich in basic nitrogen compound, for example 60% by weight 2-dimethylaminoethanol and 40% by weight Water, as an extractant for the liquid steam condensate added, you get a liquid, homogeneous mixture.
  • This liquid mixture are then one to four parts, preferably two to four parts, an alkane and / or an ester, in particular of an ethyl acetate, on part of the liquid mixture added. This creates the previously homogeneous mixture two coexisting, liquid phases, of which the water-containing Phase with high selectivity that contains free fatty acids.
  • alkane and / or ester phase are essentially those in Damper condensate dissolved fats and oils.
  • the in Damper condensate also dissolved by-products, such as tocopherols, Tocotrienols and phytosterols also go with high selectivity into the alkane phase.
  • the hydrous phase with the Free fatty acids contained therein are of low viscosity, so that a phase separation approximately within 20 minutes after the interruption the mixing has taken place.
  • the raffinate that results after separation of the aqueous phase is strong depending on the starting product on by-products such as tocopherols, phytosterols, tocotrienols enriched.
  • the extraction is from such concentrates of these valuable by-products among economically attractive Conditions possible.
  • alkanes are propane, butane, hexane, petroleum ether, Heptane, heptane fractions, octane, etc. are suitable.
  • the pressure in the mixing vessel must match the respective vapor pressure in two phases at least correspond to the butane or propane in is in liquid form.
  • the esters are particularly suitable Ethyl acetate, for example ethyl acetate, propyl acetate, butyl acetate or a mixture of them.
  • the concentration of free fatty acids in the treatment Starting material more than about 50% by weight
  • the addition of alkanes is required the entire system (starting material and extracting agent) remains two-phase.
  • the addition of alkane or ester is accordingly even with high concentrations of free fatty acids in the Starting mixture the formation of two easy to use secured liquid phases, and it can with the invention extraction agent used by an extraction in Countercurrent extracts with high concentrations of free fatty acids be preserved.
  • the solvent ratio can be small, which affects the economy of the method according to the invention has an advantageous effect.
  • a starting product becomes through a line 10 (Oil, fat or damper condensate) of a first extraction column 12 fed.
  • the free fatty acids with an extracting agent, that from a mixture of a basic nitrogen compound and water is extracted with high selectivity.
  • the extracting agent used contains at least about 20% by weight and at most about 80% by weight of the organic nitrogen compound (organic base). Concentrations have proven to be particularly favorable the basic nitrogen compound from about 30 to 40 wt .-% proven. The concentration of basic nitrogen compound can, however, be selected even higher.
  • the oil or fat freed from the free fatty acids is removed by a power 14 of a washing column 16 (extraction column) fed in with the residues of the basic nitrogen compound Water or with an aqueous solution containing an acid, be washed out, and leaves the washing column 16 as raffinate R.
  • the at the top of the washing column 16 through a line 18th escaping wash solution is then in by distillation worked up a distillation column 20. In doing so Water and possibly the volatile solution dissolved in the water
  • the acid (such as acetic acid) is distilled off until the Bottom product of the distillation column 20 the composition of the extractant has reached. This bottom product will then through a line 22 to the extractant circuit described below fed while the distillate of the Distillation column 20 as washing liquid via a line 24 of the washing column 16 already mentioned is fed.
  • the one containing the free fatty acids at the top of the extraction column 12 extracted extractant is through a line 26 fed to a second distillation column 28.
  • water and the basic nitrogen compound fall during distillation in the distillation column 28 as a top product during the the extracted free fatty acids and some containing neutral oil Extract as a bottom product through a line 30 from the Distillation column 28 is withdrawn.
  • the top product of Distillation column 28 is used as an extractant by a Line 32 fed to the extraction column 12, in which the Extraction of the free fatty acids takes place, with which the extractant circuit closed is.
  • Through lines 34 and 36 is the distillation columns 20 and 28 for distillation required energy supplied in the form of heating steam.
  • the raffinate contained 0.05% by weight of free fatty acids, 1.4% by weight of tocopherol, 0.6% by weight of stigmasterol and 97.95% by weight of neutral oil. In the extract 0.46% by weight of the amount of neutral oil used remained.
  • the raffinate minus extractant consisted of 0.3 wt .-% free Fatty acids, 0.4% by weight tocopherols, 0.1% by weight stigmasterol, and 99.4% by weight neutral oil. 6 wt .-% of the amount used Neutral oil was in the extract. The solvent ratio had the low value of 0.14.
  • 100 g of palm oil with a content of 5.5% by weight of free fatty acids were at 60 ° C with 100 g of a mixture of 30 g of N, N-dimethylamino-ethanol and 70 g of water by stirring together mixed. After the mixing process was interrupted, the Phase separation, which occurred after about 3 minutes, was waited for and samples are taken from both coexisting phases and analyzed.
  • the palm oil (raffinate) contained minus the extractant less than 0.1% by weight of free fatty acids.
  • the Extract contained less extractant 77% by weight of fatty acids and 23% by weight glycerides (mono-, di- and triglycerides; the latter the main component). About 1.2 g glycerides (about 1.2% of the Weight) were extracted together with the free fatty acids.
  • 100 g of palm oil with 4.3% by weight of free fatty acids were at 80 ° C with a solution of 40 wt.% N, N-dimethylaminoethanol in Water mixed together by stirring. After separation of the Coexisting phases were samples from each of the phases taken and analyzed.
  • the extract contained less extractant 67% by weight of fatty acids and 33% by weight of glycerides (Mono-, di- and triglycerides).
  • the raffinate contained minus Extractant less than 0.1% free fatty acids. In the extract there were 2 g of glycerides (approx. 2% of the weight). 1.9% by weight of N, N-dimethylaminoethanol were dissolved in the raffinate, that were washed out with water.
  • 100 g of palm oil with 4.2% by weight of free fatty acids were at 50 ° C with 100 g of a solution of 40% by weight of N, N-dimethylaminoethanol extracted in water.
  • the extract consisted of extractant 75% by weight of fatty acids and 25% by weight of glycerides.
  • the extract also contains 1 g Glycerides (corresponding to a 1% loss in fat).
  • the Raffinate contained 0.1% by weight of free fatty acids.
  • Palm oil was planted in a plant according to the attached figure first extraction column 12 with an amount of 30.0 kg / h fed. Since the palm oil contained 4.3% by weight of free fatty acids, the feed through line 10 consisted of 28.71 kg / h of neutral oil and 1.29 kg / h free fatty acids.
  • the extraction column 12 was the palm oil at 80 ° C with 30.0 kg / h extractant in Countercurrent brought into contact. The extractant was out Dimethylaminoethanol (DMAE) and water in a ratio of 1: 1 composed.
  • DMAE Dimethylaminoethanol
  • the one leaving the extraction column 12 Raffinate flow comprised 24.424 kg / h neutral oil, 0.090 kg / h free Fatty acids, 0.855 kg / h DMAE and 0.855 kg / h water.
  • the extract stream consisted of 14.145 kg / h DMAE, 14.145 kg / h water, 0.285 kg / h neutral oil and 1.20 kg / h free fatty acids combined.
  • the raffinate stream was fed to the washing column 16, in which at 80 ° C with 15.0 kg / h of water in countercurrent DMAE was washed out.
  • the raffinate stream thus purified left the washing column 16 in the following composition: 28.424 kg / h neutral oil, 0.012 kg / h DMAE and less than 0.025 kg / h free fatty acids. This corresponds to a neutral oil with 0.00042 % DMAE and less than 0.00088% free fatty acids.
  • the wash water left the wash column 16 with the following Composition: 15.855 kg / h water, 0.855 kg / h DMAE and 0.064 kg / h free fatty acids.
  • the wash water was in the distillation column 20 regenerated at 100 ° C. As a top product 15.0 kg / h of water through line 24 into the washing column 16 recycled. The bottom product with 0.855 kg / h of water and 0.855 kg / h DMAE is with the extract stream flowing through line 26 combined from the extraction column 12.
  • the combined with the bottom product from the distillation column 20 Extract stream from the extraction column 12 was the Distillation column 28 fed.
  • the top product of the distillation column 28 became 15.0 kg / h water and 15.0 kg / h DMAE as an extractant through line 32 into the extraction column 12 returned.
  • the distillation column left as the bottom product 28 0.285 kg / h neutral oil and 1.264 kg / h free Fatty acids.
  • the extract therefore consisted of 18.4% by weight Neutral oil and 81.6% by weight free fatty acids.

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Claims (11)

  1. Procédé pour éliminer des acides gras libres contenus dans des corps gras ou des huiles d'origine biologique par extraction des acides gras libres à l'aide d'un mélange de composés azotés organiques basiques et d'eau comme produit d'extraction à une température inférieure à la température d'ébullition des composés azotés organiques, la part des composés azotés organiques basiques contenue dans le produit d'extraction s'élevant au moins à environ 20 % en poids et au maximum à environ 60 % en poids, de préférence entre environ 30 et environ 40 % en poids, et la température d'ébullition du(des) composé(s) azoté(s) organique(s) basique(s) utilisé(s) étant égale ou supérieure à la température d'ébullition de l'eau et inférieure à la température d'ébullition des acides gras à extraire.
  2. Procédé selon la revendication 1,
    caractérisé en ce que le(s) composé(s) azoté(s) basique(s) contenu(s) dans le corps gras ou l'huile raffiné et obtenu par extraction est(sont) éliminé(s) par lavage à l'aide d'eau ou de solutions aqueuses d'acides volatiles.
  3. Procédé selon la revendication 1 ou 2,
    caractérisé en ce que, lors de la désacidification des corps gras et des huiles contenant une teneur en acides gras libres située entre environ 50 % en poids et plus, on ajoute aux matières de départ à désacidifier des alcanes et/ou un ester, en particulier un acétate d'éthyle, dans une concentration suffisante pour permettre la décomposition en deux phases du système constitué par le produit d'extraction, l'alcane et la matière de départ.
  4. Procédé pour éliminer des acides gras libres contenus dans les condensats de vapeur de corps gras ou d'huiles d'origine biologique comprenant les étapes suivantes :
    extraction des acides gras libres à l'aide d'un mélange de composés azotés organiques basiques et d'eau comme produit d'extraction à une température inférieure à la température d'ébullition des composés azotés organiques, la part des composés azotés organiques basiques contenue dans le produit d'extraction s'élevant au moins à environ 40 % en poids et au maximum à environ 60 % en poids, de préférence entre environ 50 % en poids et plus, et la température d'ébullition du(des) composé(s) azoté(s) organique(s) basique(s) utilisé(s) étant égale ou supérieure à la température d'ébullition de l'eau et inférieure à la température d'ébullition des acides gras à extraire, et
    addition de 1 à 4 parts, de préférence de 2 à 4 parts, d'alcane et/ou d'un ester, en particulier d'un acétate d'éthyle, pour 1 part de mélange homogène liquide obtenu lors de l'étape d'extraction précédente.
  5. Procédé selon la revendication 3 ou 4,
    caractérisé en ce que le(s) composé(s) azoté(s) basique(s) en phase alcane et/ou phase ester est(sont) éliminé(s) par lavage à l'aide d'eau ou de solutions aqueuses d'acides volatiles.
  6. Procédé selon l'une des revendications 2 ou 5,
    caractérisé en ce que le(s) composé(s) azoté(s) organique(s) dissout(s) dans l'eau ou les solutions aqueuses d'acides volatiles après l'étape d'élimination par lavage est(sont) séparé(s) par distillation.
  7. Procédé selon l'une des revendications 3 à 6,
    caractérisé en ce que l'alcane utilisé est du propane, du butane, du pentane, de l'hexane, de l'heptane, une fraction d'heptane, de l'octane ou un mélange de ces derniers.
  8. Procédé selon l'une des revendications 3 à 7,
    caractérisé en ce que l'ester utilisé est un acétate d'éthyle, acétate de propyle, acétate de butyle ou un mélange de ces derniers.
  9. Procédé selon l'une des revendications précédentes,
    caractérisé en ce que les acides gras extraits sont séparés du produit d'extraction par distillation sous pression atmosphérique ou sous vide du produit d'extraction contenant les acides gras.
  10. Procédé selon l'une des revendications précédentes,
    caractérisé en ce que le composé azoté organique basique utilisé est une amine tertiaire.
  11. Procédé selon l'une des revendications précédentes,
    caractérisé en ce que le composé azoté organique basique utilisé est du 2-diméthylamino-éthanol, 2-méthylamino-diéthanol,
    4-méthylmorpholine, 2-diisopropylamino-éthanol, 2-dibutylamino-éthanol, 3-diméthylamino-propanol, 1-diméthylamino-2-propanol, 2-diméthylamino-éthanol, 2-diméthylamino-1-butanol, 2-(méthyléthylamino)-éthanol, diméthylformamide, morpholine, pyridine, 2-diméthylamino-2-méthyl-1-propanol, 4-méthyl-pyridine, 1-méthyl-pyrrol, 2-dibutylamino-éthanol, 2-diméthylamino-éthylamine, monoéthanolamine, 3-diméthylamino-1-propanol, diméthylamino-2-propanone, 1-diméthylamino-1-propylènamine, ou un mélange de ces composés.
EP00922646A 1999-04-21 2000-04-18 Procede pour eliminer des acides gras libres, contenus dans des corps gras et des huiles d'origine biologique ou dans leurs condensats de vapeur Expired - Lifetime EP1171555B1 (fr)

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DK00922646T DK1171555T3 (da) 1999-04-21 2000-04-18 Fremgangsmåde til fjernelse af frie fedtsyrer fra fedtstoffer og olier af boplogisk oprindelse eller deres dampkondensater

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DE19918097 1999-04-21
DE19918097A DE19918097C2 (de) 1999-04-21 1999-04-21 Verfahren zur Entfernung freier Fettsäuren aus Fetten und Ölen biologischen Ursprungs oder deren Dämpferkondensaten
PCT/EP2000/003498 WO2000063327A2 (fr) 1999-04-21 2000-04-18 Procede pour eliminer des acides gras libres, contenus dans des corps gras et des huiles d'origine biologique ou dans leurs condensats de vapeur

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US (1) US6579996B2 (fr)
EP (1) EP1171555B1 (fr)
JP (1) JP3711023B2 (fr)
CN (1) CN1133736C (fr)
AR (1) AR023552A1 (fr)
AT (1) ATE269387T1 (fr)
AU (1) AU756898B2 (fr)
BR (1) BR0009895A (fr)
CA (1) CA2370785A1 (fr)
DE (2) DE19918097C2 (fr)
DK (1) DK1171555T3 (fr)
ES (1) ES2218150T3 (fr)
IL (1) IL145977A (fr)
MX (1) MXPA01010698A (fr)
PL (1) PL350431A1 (fr)
RU (1) RU2242505C2 (fr)
TR (1) TR200103038T2 (fr)
UA (1) UA71958C2 (fr)
WO (1) WO2000063327A2 (fr)

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DE10164274B4 (de) * 2001-12-27 2005-12-29 Energietechnik Leipzig Gmbh Verfahren und Vorrichtung zur kontinuierlichen Extraktion von freien Fettsäuren, Tocopherolen und/oder Sterolen aus nativen Ölen und zur Umesterung nativer Öle
NL1020603C2 (nl) * 2002-05-15 2003-11-18 Tno Werkwijze voor het drogen van een product met behulp van een regeneratief adsorbens.
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US6579996B2 (en) 2003-06-17
IL145977A0 (en) 2002-07-25
JP3711023B2 (ja) 2005-10-26
BR0009895A (pt) 2002-01-15
AU756898B2 (en) 2003-01-23
AR023552A1 (es) 2002-09-04
MXPA01010698A (es) 2002-06-04
WO2000063327A3 (fr) 2001-04-05
ATE269387T1 (de) 2004-07-15
IL145977A (en) 2004-12-15
CN1133736C (zh) 2004-01-07
CA2370785A1 (fr) 2000-10-26
US20020111504A1 (en) 2002-08-15
PL350431A1 (en) 2002-12-16
DE50006822D1 (de) 2004-07-22
CN1347445A (zh) 2002-05-01
DE19918097A1 (de) 2000-12-21
JP2002542379A (ja) 2002-12-10
RU2242505C2 (ru) 2004-12-20
AU4296400A (en) 2000-11-02
DE19918097C2 (de) 2003-12-24
EP1171555A2 (fr) 2002-01-16
TR200103038T2 (tr) 2002-03-21
DK1171555T3 (da) 2004-11-01
ES2218150T3 (es) 2004-11-16
WO2000063327A2 (fr) 2000-10-26
UA71958C2 (en) 2005-01-17

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