EP0545292A2 - Procédé pour éliminer des stérols de graisses végétales et animales - Google Patents

Procédé pour éliminer des stérols de graisses végétales et animales Download PDF

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EP0545292A2
EP0545292A2 EP92120234A EP92120234A EP0545292A2 EP 0545292 A2 EP0545292 A2 EP 0545292A2 EP 92120234 A EP92120234 A EP 92120234A EP 92120234 A EP92120234 A EP 92120234A EP 0545292 A2 EP0545292 A2 EP 0545292A2
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fat
water
cholesterol
hydrocarbon
phase
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EP0545292A3 (en
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Siegfried Prof. Dr. Peter
Bernd Dr. Czech
Eckhard Dr. Weidner
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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
    • C11B3/006—Refining fats or fatty oils by extraction

Definitions

  • the present invention relates to a method for separating sterols from or for enriching sterols in vegetable and animal fats. Since cholesterol is by far the most important of these sterols, the separation / enrichment of cholesterol is generally discussed below as being representative of the separation / enrichment of the sterols in general.
  • Cholesterol (5-choleston-3 ⁇ -ol), MW 386.64, melting point 148.5 ° C, boiling point 360 ° C, is practically insoluble in water, little in alcohol in the cold, more soluble in heat. Cholesterol is readily soluble in ether, benzene, petroleum ether and chloroform. Cholesterol is found in large amounts in gallstones. As the main representative of zoosterols, cholesterol is also widespread in the other organs: in the cerebrum (approximately 10% of the dry matter), in nerve cells, in the adrenal glands and in the skin. Egg yolk and wool wax are also high in cholesterol. The blood contains 150 to 250 mg%, the heart 2000 mg% cholesterol (maximum amount around the 60th year of life).
  • the human body contains an average of 0.32% cholesterol, partly free, partly esterified with fatty acids: the esters are included in the blood lipids.
  • the esters are included in the blood lipids.
  • About 1 to 2 g of cholesterol are synthesized and added to in the body of the adult every day low-fat diet 0.04 to 0.1 g, with high-fat diet up to 1.4 g cholesterol.
  • Each 100 g of food contains butter 240 mg, margarine 186 mg, fatty beef 90 mg, fatty pork 99 mg, cod 58 mg, haddock 64 mg and cod liver oil 570 mg cholesterol.
  • Cholesterol also occurs in small amounts in vegetable fats. Cholesterol is biosynthesized from squalene via lanosterol. The main place of formation is the liver, but cholesterol is also formed in the adrenal cortex, skin, intestine, testes and aorta.
  • cholesterol is the biogenetic precursor of bile acids, vitamin D3, androsterone, testosterone, progesterone and other steroids. Cholesterol also plays a role in the organism as a skin protection substance, swelling regulator, nerve isolator and the like.
  • oils with a high content of unsaturated fatty acids e.g. sunflower oil, corn oil, linseed oil, soybean oil and grape seed oil
  • sunflower oil, corn oil, linseed oil, soybean oil and grape seed oil should lower blood cholesterol levels and thus in many cases work against arteriosclerosis.
  • the raw material for butter production is cream, a fat-enriched milk emulsion with 20 to 25% fat content. It is obtained when the milk is left to stand or centrifuged. By continuously beating in the churn or in the butter machine the cream is transformed into butter. The very fine fat particles gradually combine to form larger lumps. 1 kg of butter is generally obtained from 25 l of good milk.
  • the aqueous phase that forms is buttermilk.
  • the finished unsalted butter contains an average of 82 to 84% fat and 15% water as well as smaller amounts of lactose, lactic acid, casein, protein and minerals. From a colloid chemistry standpoint, butter is a water-in-oil emulsion, whereas milk is an oil-in-water emulsion. In the latter case, very fine fat particles float in an aqueous solution.
  • clarified butter is made from butter, which is 99.3% butter fat.
  • the clarified butter contains a maximum of 0.5% water and is practically free of lactose, casein and salts.
  • the clarified butter is produced by melting the butter and separating the aqueous phase with heating to 100 to 105 ° C. It usually serves as frying and shortening.
  • the color of the butter is related to the feeding of the dairy cows and the vitamin content of the feed.
  • Butter fat contains 0.2 to 0.45% lecithin, 0.22 to 0.41% cholesterol and the fat-soluble vitamins A and E.
  • Lactic acid bacteria are present in the butter up to 100 million / g, which is, however, harmless to health. It is best kept dark and cool to protect against becoming rancid. In the presence of heavy metal ions (especially copper) and higher acidity, butter can have a fish-like odor after only 2 to 3 days, because the lecithin in the butter is broken down into trimethylamine by hydrolysis and oxidation.
  • milk fat consists of triglycerides.
  • the carbon number of the triglycerides is in the range from 26 to 54.
  • the remaining 2% consist of a large number of other compounds, e.g. Lecithin, cholesterol, vitamins A and E, and a large number of other components that contribute to the characteristic taste of milk fat and are present in low concentrations.
  • the flavors of the butter are formed partly due to enzymatic processes during cream ripening and partly through the autoxidation of unsaturated fatty acids.
  • the main flavors of the cream are diacetyl (2,3-butanedione) and acetoin (3-hydroxy-2-butanone).
  • the following flavorings are also important: unsaturated aldehydes such as cis-4-heptenal and homologs, esters and lactones. From the lactones, ⁇ -decalactone, ⁇ -dodecalactone, ⁇ -tetradecalactone and ⁇ -hexadecalactone could be identified.
  • Another proposed method concerns the dissolution of the cholesterol-containing material in a non-polar solvent such as e.g. Hexane and the subsequent adsorption of the cholesterol on silica gel (JP-B-62-039593).
  • a non-polar solvent such as e.g. Hexane
  • Another work reports that cholesterol is adsorbed at the heptane / water interface together with alkylammonium (cetyltrimethylammonium, dioctyldimethylammonium) (Yu.A. Shchipanow, AN Popow, Latv. PSR Zinat. Akad. Vestis, Kim. Ser. ( 4), 445-51, 1980).
  • the food is then spun in a centrifuge to separate the cholesterol-laden BCD.
  • a centrifuge says Sidhu, 80 to 90% of the cholesterol could be removed.
  • a real advantage of BCD technology is that it works at temperatures down to 5 ° C. This means that Food cannot be spoiled by heating and can be cooled during manufacture to prevent the growth of microorganisms. He says that many food processing companies already have the necessary equipment and the BCD can be manufactured cheaply.
  • CSIRO signed a license agreement with an Australian company, National Eggs Products, earlier this year.
  • the company is in the process of starting the production of eggs in liquid or dry form with low cholesterol.
  • the health-promoting eggs could be used in a wide range of foods, from egg flip and ice cream to confectionery and mayonnaise.
  • sterols such as cholesterol, stigmasterol, sitosterol, lanosterol, agnosterol, etc. are soluble in alcohol.
  • the milk fat was stripped with steam at 70 ° C for 15 minutes to remove all traces of organic solvent residues. At this point the milk fat was ready for use in the manufacture of the various products.
  • water-miscible solvent means an organic solvent which is liquid at 20 ° C. and atmospheric pressure and is preferably miscible with water in any ratio. In any case, however, at least 10% by weight of water should dissolve in solvent (under the conditions just mentioned).
  • Preferred hydrocarbons are volatile (preferably saturated) hydrocarbons with a carbon number of 1 to 12, for example 1 to 8, in particular 1 to 4. Specific examples of this are methane, ethane, propane and butane, that is to say hydrocarbons which are used in food technology without restriction allowed are. These hydrocarbons can be easily separated from the treated fat after extraction at low temperatures. In the case of hydrocarbons boiling at temperatures below the extraction temperature, the extraction must take place at the respective vapor pressure or above. In addition, with the above preferred alkanes, the concentration thereof in the fat can be controlled very easily and reliably by means of the pressure.
  • Water-miscible solvents suitable for the process according to the invention are e.g. Alcohols, ketones, carboxylic acid esters and mixtures thereof. Alcohols, in particular alkanols, having 1 to 6, preferably 1 to 3, carbon atoms, such as e.g. Methanol, ethanol and propanol. Ethanol and isopropanol are particularly preferred, ethanol being the alcohol of choice in most cases.
  • the alcohol can also have more than one (e.g. two or three) hydroxyl groups and ether bridges. Examples of these are ethylene glycol, diethylene glycol, propanediol etc.
  • ketones are those with 3 to 5 carbon atoms, e.g.
  • Acetone and butanone are preferred, while for the carboxylic acid esters the total carbon number should also not exceed 5 (e.g. in the case of methyl formate and ethyl acetate).
  • alcohols are by far the most preferred as water-miscible solvents according to the invention, the term “alcohol” or “alkanol” is always used as a representative for "water-miscible solvent”, but this does not mean that the corresponding statements are limited to the cases in which actually use alcohols or alkanols.
  • the alcohols are noticeably dissolved in the fat phase during the extraction and must be removed from the raffinate after the sterols have been extracted. This is done conventionally by stripping at elevated temperatures and reduced pressure (approx. 70 to 80 ° C; 0.1 - 0.5 bar). The stripping process generally takes about 15 minutes.
  • This temperature load can now be avoided by the methods of this invention by using methane, ethane, propane or butane as hydrocarbons.
  • the raffinate phase is heated to about 20 ° C. above the process temperature and then expanded to a pressure of 0.5 to 1 bar via a relief valve.
  • the alkane is released in gaseous form and almost completely transports the dissolved alcohol out of the fat phase. In this way, a short and moderate increase in temperature is sufficient to free the raffinate from the solvents. Should there still be traces of alcohol in the fat, a further dissolution of one of the alkanes mentioned (e.g. methane at a pressure of 5 bar) and subsequent relaxation is sufficient to remove the last residues of alcohol.
  • the weight ratio of alcohol used to water used in the process according to the invention is generally 1: 0.05 to 1: 1, in particular 1: 0.07 to 1: 0.5, a ratio in the range from 1: 0.1 to 1 : 0.35 particularly preferred is.
  • the greater the ratio of water to alkanol the lower the alcohol content of the fat.
  • the solubility of the hydrocarbon in the alcohol decreases with increasing water content of the alcohol.
  • the alcohol content of the fat and the hydrocarbon content in the alcohol increase with a reduced water content of the alcohol.
  • water concentrations greater than 15% by weight will not be used, for example, when extracting cholesterol from milk fat with the help of ethanol, since otherwise the solubility of the cholesterol would be too low and the required amounts of extractant would become too large.
  • the weight ratio of fat to be extracted to hydrocarbon / alcohol / H2O mixture in the process according to the invention is normally 1: 0.5 to 1:10, in particular 1: 1 to 1: 7, with a weight ratio of 1: 2 to 1: 5 being particularly preferred is preferred.
  • stage d) of the process according to the invention the partial removal of the solvent, preferably achieved by distillation, is preferably carried out up to a residual alcohol content of 0.1 to 10, in particular 0.5 to 3,% by weight.
  • the above process is preferably carried out so that the weight ratio of alcohol to water in the extracting agent used in stage (ii) is in the range from 15: 1 to 1: 1, in particular 10: 1 to 1.5: 1.
  • the hydrocarbon which may be present in these extractants preferably makes up no more than 20% by weight, in particular no more than 10% by weight, of the extractant used.
  • the weight ratio of the fat to hydrocarbon to be extracted is preferably 8: 1 to 1: 5, particularly 6: 1 to 1: 3.
  • the content of the alcohol in the solvent for the fat is generally not more than 20% by weight, in particular not more than 10% by weight.
  • the amounts of water which may be present in such a mixture generally originate from the water content of the alcohol used and are accordingly in the trace range up to approximately 5% by weight, in particular approximately 1% by weight.
  • the weight ratio of the fat-rich phase to the water-alcohol phase in the above extraction is in the range from 0.4: 1 to 5: 1. With increasing phase ratio, the yield of sterin-poor fat increases. With the right choice of the phase ratio and the ratio of hydrocarbon: alcohol: water: fat and especially with counterflow with return recoveries of 95 to 99% of low-sterol or sterol-free product can be obtained, the sterol content of which can be reduced to 0.01% by weight.
  • the process according to the invention can be carried out, for example, in such a way that the starting product, for example butter oil, is dissolved in a hydrocarbon in a mixer.
  • the solution of the fat to be freed from sterol (in particular cholesterol) is fed to an extraction column at the bottom and the extraction agent (alcohol / water mixture) is fed to the extraction column at the top.
  • the extractant normally forms the heavy phase and flows through the column in countercurrent to the solution of the fat from top to bottom.
  • the alcohol / water phase can also be the easier phase. In this case the flow directions change accordingly.
  • the sterols dissolve in addition to some fat in the extractant.
  • the extract is fed to a rectification column and the alcohol is removed to a residual content of preferably about 0.5 to 2%. If thermal treatment is important, rectification is carried out under reduced pressure or by stripping.
  • the alcohols methanol, ethanol and isopropanol (as well as acetone) are generally preferred because they have the lowest boiling points.
  • the solubility of the fat in the extract phase has dropped to practically 0.
  • the dissolved fat floats and is preferably separated by decanting or centrifuging.
  • the extracted sterol is practically completely dissolved in the precipitated oil (fat).
  • products up to a sterol content of 5% and above can be obtained. These products are suitable as raw materials for the production of pure sterols (especially pure cholesterol), if necessary after repeating the process according to the invention.
  • Cholesterol is of economic interest, for example, as a starting product for the synthesis of steroid hormones and liquid crystals.
  • the remaining water is preferably mixed with the top product from the rectification of the extract phase and returned to the top of the extraction column as the extraction agent.
  • the water-soluble flavors such as those found in butter oil, remain dissolved in water in the course of the process according to the invention and are thus returned to the process.
  • the aroma of the product to be freed from sterols is practically retained.
  • the fatty acid pattern can only be influenced in the ratio of the amount of fat in the two phases. With a yield of 95% and above, no change of importance is to be expected.
  • Another possibility of returning the flavoring substances dissolved in water to butterfat is that when the alcohol is separated from the alcohol-rich phase by distillation, so much water is distilled off that the amount of flavoring water obtained is just sufficient to remove from the sterol-free or low-purity Make butterfat spreadable butter by emulsifying the water.
  • cholesterol is to be removed from butter oil (milk fat).
  • Butter oil and hydrocarbon are mixed in the mixer (1) at a temperature slightly above the melting temperature of the butter fat in the desired ratio, so that a homogeneous solution is obtained.
  • the minimum pressure in the mixer is determined by the vapor pressure of the hydrocarbon above the solution. It may be advantageous to add some alcohol to the solution.
  • the homogeneous solution is fed to the extraction column (2) at the bottom. It flows in the column upwards and against the alcohol / water phase. The cholesterol is absorbed by the alcohol / water phase. A small amount of fat also passes into the alcohol / water phase. The light phase freed from cholesterol leaves the extraction column at the top and enters column (3).
  • the temperature in the extraction column can be below the temperature in the mixer. It can be freely selected down to freezing point.
  • the operating pressure in the extraction column is higher than atmospheric pressure.
  • the solvent of the fat-rich phase (the raffinate) is largely separated from the dissolved fat in a flash process in the column (3) at a temperature which is about 20 to 40 ° C. higher than the temperature in the extractor.
  • the liquid phase is then depressurized to atmospheric pressure in the expansion valve (4) and fed to the distillation column (5), in which the hydrocarbon, alcohol and water portions still dissolved in fat are separated off.
  • the solvent separated off in the column (3) is returned to the mixer (1).
  • the alcohol / water phase (the extract) is largely freed from the volatile hydrocarbon by a flash process and then in the raffinate phase in column (6) at temperatures of 20 to 40 ° C above the temperature in the extraction column Relief valve (7) brought to atmospheric pressure.
  • the extract which leaves the bottom of the extraction column (2), is fed to the rectification column (8). It consists of a mixture of alcohol and water as the main components, in which, in addition to some fat and hydrocarbon, the extracted cholesterol is dissolved.
  • the rectification column (8) works at atmospheric pressure.
  • the extract is divided into a top product, which contains alcohol as the main component and small amounts of hydrocarbon in addition to water, and in one Bottom product of water with low alcohol content (about 1%) and fat broken down.
  • the fat When the alcohol is separated from the aqueous phase, the fat becomes insoluble and separates out as an oil. The latter surprisingly contains the extracted cholesterol practically completely dissolved.
  • the oil is separated in the separator (9) by decanting or centrifuging.
  • the remaining aqueous phase contains the extracted water-soluble flavors of the feed and traces of cholesterol.
  • the fat obtained in separator (9) can contain up to about 5% cholesterol.
  • the water phase from separator (9) is combined with the top product of column (8) and returned to the top of the extraction column (2). In this way, according to the method according to the invention, a fat can be freed of cholesterol without environmental problems having a high yield (96 to 98% can be obtained as cholesterol-free fat), because solvents and extracting agents are completely returned to the method.
  • the milk fat is characterized by a particularly broad fatty acid pattern compared to the usual dietary fats, as can be seen from Table 1 below.
  • a special feature is the relatively high content of butyric acid and caproic acid. This includes the physiological value of milk fat.
  • TABLE 1 Composition of the fatty acid mixtures obtained from some natural fats Percentage of the fatty acid mixture butter Lard Coconut fat olive oil Butyric acid (C4) 3rd - - - Caproic acid (C6) 2nd - - - Caprylic acid (C8) 1 - 8th - Capric acid (C10) 2nd - 7 - Lauric acid (C12) 4th - 47 - Myristic acid (C14) 10th 3rd 18th - Palmitic acid (C16) 28 25th 9 9 9 Stearic acid (C18) 10th 10th 2nd 2nd Sum of saturated fatty acids 60 38 91 11 Oleic acid (C18) 35 52 6 85 Linoleic acid (C18) 5 10th
  • the solvent ratio is chosen to be small, for example 1: 1, the loss of milk fat can be reduced, for example to 5%. As a result, the fatty acid pattern is changed little. The loss of flavorings is also less. However, in this case it is not possible to reduce the cholesterol content to extremely low values with a simple countercurrent extraction.
  • Butter oil (milk fat) and hydrocarbon are mixed in mixer (10) at a temperature slightly above the melting temperature of the butter oil in the desired ratio so that a homogeneous solution is formed. It may be advantageous to add enough alcohol (e.g. ethanol) to the solution to maintain the equilibrium concentration in the extractor.
  • the pressure in the mixer (10) corresponds to the vapor pressure of the hydrocarbon over the solution.
  • the homogeneous solution is fed to the extraction column (11) in a central section.
  • the temperature in the extraction column (11) can be below the temperature in the mixer (10). It can be freely selected down to freezing point.
  • the extract phase can be the heavy or the light phase.
  • the content in butter oil can be adjusted and regulated by the pressure. If the butter oil has a high alkane content and the alkanol has a higher water content, the extract phase is the difficult phase. With lower alkane levels in butter oil and low water levels in the alkanol, the extract phase is the light phase. The alkane content of the butter oil and the water content of the alkanol are adjusted so that the density difference between the extract and raffinate phases is at least 50 kg / m3.
  • Extract phase and raffinate phase are carried out in countercurrent in the extraction column (11).
  • Cholesterol is absorbed by the extraction agent, which consists of alkanol and water. It also extracts a small amount of fat dissolved.
  • the raffinate phase freed from cholesterol leaves the extraction column (11) and reaches the flash evaporator (12).
  • the temperature in the extraction column (11) in the case where methane, ethane, propane or butane is used as the alkane, the majority of the alkane and the greater part the alkanol dissolved in the butter oil is separated at the working pressure in the evaporator (12) and returned to the mixer (10).
  • the butter oil is then expanded to atmospheric pressure in the expansion valve (13) and fed to the rectification column (14).
  • the extract leaving the extraction column (11) goes into the flash evaporator (15). There, in analogy to the procedure for the raffinate phase, the dissolved alkane and part of the alkanol are separated off at elevated temperature and returned to the column (11). The extract is then brought to ambient pressure in the expansion valve (16) and fed to the rectification column (17).
  • the extract consists of a mixture of alcohol and water, in which, in addition to some fat, the extracted cholesterol and small amounts of alkane are dissolved.
  • the extract is broken down into a top product which contains alkanol as the main component and, in addition to water, small amounts of hydrocarbon, and into a bottom product of water with a low alkanol content (about 1%) and fat.
  • the fat becomes insoluble and separates as an oil.
  • the latter surprisingly contains the extracted cholesterol practically completely solved.
  • the oil is separated from the aqueous phase in the separator (18) by decanting or centrifuging.
  • the remaining aqueous phase contains the extracted water-soluble flavors and traces of cholesterol.
  • the milk fat obtained in the separator (18) contains the extracted cholesterol in concentrations of up to 5% by weight. A part of this product (about 50 to 70%) is returned to the extraction column (11) at the point of exit of the extractant as reflux.
  • the light phase contained 60 g butter oil dissolved in a mixture of 106 g hexane, 0.6 g water and 9 g ethanol.
  • the light phase butter oil had a cholesterol content of 0.19% by weight.
  • the heavy phase contained 1% by weight of butter oil dissolved.
  • the ratio of ethanol to water in the heavy phase was 4.3: 1.
  • Light phase hexane and ethanol were distilled off, thereby obtaining 59.5 g of butter oil having a reduced cholesterol content of 0.19% by weight. This corresponds to a recovery of butterfat of around 98%.
  • the ethanol was distilled off from the heavy phase using a Vigreux column to a residual content of about 1% by weight.
  • the resulting dissolved butter oil was decanted. It contained 3.7% by weight of cholesterol.
  • the water remaining after the ethanol had evaporated contained only traces of cholesterol.
  • the butter oil-rich phase was surprisingly heavier than the ethanol-rich aqueous phase.
  • the weight ratio of butterfat-rich to ethanol-rich phase was 0.39: 1.
  • the light, ethanol-rich phase was placed in a Vigreux column and the ethanol was stripped down to a residue of about 1% by weight.
  • the dissolved butter oil became insoluble and floated up.
  • the cholesterol content of the butter oil separated from the heavy phase was 1.2% by weight.
  • the water part of the heavy phase contained only traces of cholesterol.
  • the recovery of butter oil was 87% by weight.
  • the light phase contained 59 g butter oil, which was dissolved in 148 g propane, 24 g ethanol and 2 g water.
  • the cholesterol content of the butter oil dissolved in the light phase was 0.22% by weight.
  • the heavy phase consisted of 18 g water, 66 g ethanol, 12 g propane and 1 g butter oil. In the latter, the extracted cholesterol was dissolved in a concentration of 2.2% by weight.
  • the ethanol was separated from the heavy phase by distillation. The dissolved butter oil failed. After the distillation, the water contained about 1% by weight of ethanol and only traces of cholesterol.
  • the butter oil had a cholesterol content of 0.027% by weight.
  • the water phase was combined with the distillate and pumped back to the top of the extraction column as extractant. After the pump, the gaseous product from the flash process was mixed into the extractant stream. The extracted cholesterol was almost completely dissolved in the precipitated butter oil. The water phase only contained traces of cholesterol. 5.1% by weight of cholesterol were dissolved in butter oil of the extract. The recovery of cholesterol-free butterfat was 95%.
  • the extract contained 3% by weight of butterfat dissolved. It was also freed from the solvent in a rotary evaporator at 120 ° C and water jet vacuum. The remaining butterfat contained 5.5% by weight of cholesterol.
  • the light phase contained 19.7 g butterfat dissolved in a mixture of 36 g isohexane, 12 g isopropanol and 2.5 g water.
  • the solvent was distilled off to obtain 19.7 g of a butter fat with a cholesterol content of 0.21% by weight (recovery of butter fat 98.5%).
  • the weight ratio of isopropanol to water in the heavy phase was 2.3: 1.
  • the isopropanol was distilled off from the heavy phase except for a residue of about 1% by weight.
  • the dissolved butter oil failed, which was then decanted off. It contained 3.5% cholesterol in solution.
  • the aqueous phase remaining after the isopropanol had evaporated contained only traces of cholesterol.
  • the bottom product with an ethanol content of about 1% by weight was fed to a separator (9) together with the precipitated butter oil and separated into the water phase and oil phase.
  • the water phase was combined with the distillate and pumped back to the top of the extraction column (2) as the extractant. After the pump, the product from the flash process was mixed into the extractant stream.
  • the extracted cholesterol was almost completely dissolved in the precipitated butter oil.
  • the water phase only contained traces of cholesterol. 5.0% by weight of cholesterol were dissolved in butter oil of the extract.
  • the yield of cholesterol-free butter oil was 95%.
  • the raffinate was depressurized to a pressure of 0.2 bar by means of a reducing valve (22) and at this pressure and a bottom temperature of 80 ° C., ethanol and residues of Separated propane from butter fat.
  • a reducing valve (22) As the bottom product, 183 g of butter oil were withdrawn per hour from the distillation column (23). The butter oil had a cholesterol content of 0.02% by weight.
  • the top product from ethanol and propane was condensed and returned to the dissolving vessel (19).
  • the bottom product with an ethanol content of about 1% by weight was fed to a separator (29) together with the precipitated butter oil and separated into the water phase and oil phase.
  • the water phase was combined with the distillate and pumped back as extractant into the bottom of the extraction column (20). After the pump, the extractant flow became the Product blended from the flash process.
  • the extracted cholesterol was almost completely dissolved in precipitated butter oil.
  • the water phase only contained traces of cholesterol.
  • the butter oil of the extract contained 12% by weight of cholesterol dissolved.
  • the yield of cholesterol-free butter oil was 98%.
  • the upper liquid phase consisted of 12 g butter oil, 10 g propane, 739 g acetone and 91 g water.
  • the butter oil in this phase contained 1.21% by weight of cholesterol.
  • the weight ratio of the light (solvent-rich) liquid phase to heavy (butter oil-rich) liquid phase was about 3: 1.
  • the yield of reduced cholesterol butter oil was 94%.
  • the acetone was distilled off from the solvent-rich liquid phase with the aid of a Vigreux column to a residual content of about 1% by weight.
  • the resulting butter oil was decanted.
  • the water remaining after the acetone had evaporated contained only traces of cholesterol.
  • the bottom product with an ethanol content of about 1% by weight was fed to a separator (39) together with the precipitated butter oil and separated into the water phase and oil phase.
  • the water phase was combined with the distillate and pumped back as extractant into the bottom of the extraction column (31). After the pump, the product from the flash process was mixed into the extractant stream.
  • the extracted cholesterol was almost completely dissolved in the precipitated butter oil.
  • the water phase only contained traces of cholesterol.
  • the butter oil of the extract contained 12% by weight of cholesterol dissolved.
  • the yield of cholesterol-free butter oil was 98%.

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EP19920120234 1991-11-29 1992-11-26 Method of removing sterols from vegetable and animal fats Withdrawn EP0545292A3 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4139398 1991-11-29
DE19914139398 DE4139398C1 (fr) 1991-11-29 1991-11-29

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EP0545292A2 true EP0545292A2 (fr) 1993-06-09
EP0545292A3 EP0545292A3 (en) 1993-11-10

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EP19920120234 Withdrawn EP0545292A3 (en) 1991-11-29 1992-11-26 Method of removing sterols from vegetable and animal fats

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EP (1) EP0545292A3 (fr)
JP (1) JPH05230494A (fr)
AU (1) AU2968692A (fr)
CA (1) CA2083723A1 (fr)
DE (1) DE4139398C1 (fr)

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* Cited by examiner, † Cited by third party
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WO1997003566A1 (fr) * 1995-07-20 1997-02-06 Unilever N.V. Aromatisation d'huiles comestibles
DE10037515C1 (de) * 2000-08-01 2002-02-28 Sueddeutsche Kalkstickstoff Verfahren zur Abtrennung von Sterinen und/oder deren Derivaten aus einer Lipidmatrix mit Hilfe komprimierter Kohlenwasserstoffe

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4407917C2 (de) * 1993-03-15 2002-12-12 Sueddeutsche Kalkstickstoff Verfahren zur Gewinnung von Lipidfraktionen aus pulverförmigen Eiprodukten
US6166230A (en) * 1996-05-15 2000-12-26 Gist-Brocades B.V. Sterol extraction with polar solvent to give low sterol, high triglyceride, microbial oil
DE19820032A1 (de) * 1998-05-05 1999-11-11 Aev Altmark Eiveredlung Gmbh Eiprodukte mit stark reduziertem Cholesteringehalt und Verfahren zu deren Herstellung
WO2011081119A1 (fr) * 2009-12-29 2011-07-07 不二製油株式会社 Procédé permettant de réguler la production de chloropropanols et de substances formant du chloropropanol dans des huiles et des graisses de triglycérides
WO2016096988A1 (fr) * 2014-12-19 2016-06-23 Dsm Ip Assets B.V. Procédé d'extraction du cholestérol hors de matières grasses laitières
JP6517180B2 (ja) * 2016-12-07 2019-05-22 マルハニチロ株式会社 魚介類エキスからの成分を有効成分として含む塩味増強用調味料及びその用途
US11629309B2 (en) * 2017-09-14 2023-04-18 Fermenta Biotech Limited Solvent free process for extraction of cholesterol from milk fat

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1360759A (fr) * 1963-03-20 1964-05-15 Eastman Kodak Co Procédé de séparation des tocophérols et des stérols des boues de désodorisation et produits analogues
NZ223508A (en) * 1988-02-12 1991-07-26 New Zealand Dairy Res Inst A method of reducing sterols in edible fats and oils

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997003566A1 (fr) * 1995-07-20 1997-02-06 Unilever N.V. Aromatisation d'huiles comestibles
US5976595A (en) * 1995-07-20 1999-11-02 Unilever Patent Holdings Flavoring of edible oils
DE10037515C1 (de) * 2000-08-01 2002-02-28 Sueddeutsche Kalkstickstoff Verfahren zur Abtrennung von Sterinen und/oder deren Derivaten aus einer Lipidmatrix mit Hilfe komprimierter Kohlenwasserstoffe

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AU2968692A (en) 1993-06-03
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JPH05230494A (ja) 1993-09-07
CA2083723A1 (fr) 1993-05-30

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