The method of obtaining stanulovic esters

 

(57) Abstract:

The invention relates to a method for preparing stanulovic esters by hydrogenation of the composition of sterols in the solvent for the hydrogenation process and at elevated temperature in the presence of a hydrogenation catalyst with subsequent removal of the hydrogenation catalyst from the resulting hot solution, followed by transesterification intermediate composition stanilov with methyl ester of fatty acids at elevated temperatures and in the presence of an interesterification catalyst, and finally cleaning the thus obtained composition stanulovic esters. According to the invention, the intermediate composition of Stanlow not crystallize or removed from the reaction solution, and the solvent for the hydrogenation process at least partially replaced by a reagent of the process of interesterification. An alternative solvent for the hydrogenation process may be used as solvent for the process of interesterification and preferably also represents the reagent process of interesterification.

The invention relates to a method for stanulovic esters, in particular by hydrogenation, Armenia Sterol in the appropriate stanol or composition of Stanlow, with the subsequent removal of hydrogenation catalyst formed from the reaction solution, followed by transesterification of stanol or composition of Stanlow with ether containing lower alkyl, at elevated temperature and in the presence of an interesterification catalyst, and finally the thus obtained stanulovic ether or composition stanulovic esters undergo purification step.

Compounds containing stanol, are usually present in plants and animals, albeit in small quantities. Connection Sterol in most cases present in animals in the form of cholesterol. The Sterol compounds present in plants usually consist of several sterelny structures that have structural similarities between them. Among the latter the most often-sitosterol, campesterol and sigmasterol. Depending on the sources of plant materials can also contain various other compounds that have similarities with the above sterols, such as brassicasterol in rape-sitosterol and Betulinol in the birch, methylenecycloartanol and cycloartenol, avenasterol etc.

Sterols contained in wood materials also include saturated Streatham saturated carbon-carbon linkages. These compounds are called stanolone. Stanol corresponding to the most common plant Sterol-sitosterol, is the so-sitostanol. The process of hydrogenation of Stanlow described, for example, "Organic Preparations and Procedures" 1 (2) (1969) 107-109 (Augustine, R. L. and Reardon Jr, E. J. : The Palladium catalyzed hydrogenation of cholesterol) and in "Atherosclerosis" 24 (1975) 301-309 (Sugano, M. et al. : Lipid-lowering activity of phytosterols in rats).

Cholesterol is a necessary compound for the human body, as well as other vertebrates, for example, as an ingredient of skeletal structures. In high concentrations, however, cholesterol is harmful, as it accumulates on the walls of blood vessels and increases the risk of cardiovascular disease.

In research it has been observed that plant compounds containing a Sterol, and, in particular, plant compounds that contain stanol added to the diet, the lower the concentration of cholesterol in serum in humans. In the case when, for lowering cholesterol, it is desirable to use compounds that are derived from plant sterols, from the point of view of efficiency and applicability of these compounds, it is important that they are placed in a suitable x the form of the use of plant compounds, containing a Sterol, is the translation of these compounds in the saturated form of Stanlow and esterification them with fatty acids. In this case, on the one hand, the functional effectiveness of the compounds is very high and, on the other hand, being fat-soluble, they can easily be added to various food products.

The method traditionally used to obtain the considered compounds, so-called stanulovic esters, corresponds to the way in which in the first stage, the Sterol is subjected to catalytic hydrogenation in the solvent hydrogenation process. Hydrogenated Sterol (stanol) crystallized and subsequently filtered from the reaction mixture, and then applied to the process of transesterification, in which the reagent interesterification is usually the methyl ester of vegetable oil (South African patent ZA 96/7616).

The known method described above has the disadvantage that the cost stanovova ether produced by the above method becomes relatively high due to the high capital costs required to filter the crystallized intermediate compounds containing stanol. Schitalos is but to be separated from the reaction mixture before the process of interesterification.

Thus, the goal of the present invention is the creation of more perfect than the previous method of obtaining soluble stanulovic esters, this simplifies the process of obtaining stanulovic esters and reduced capital costs for obtaining stanulovic esters, provided almost quantitative yield, which maximized the production of the final product stanovova ether with high quality.

Thus, the present invention provides a method of obtaining stanovova ether, like described in the restrictive part of the first claim, the main characteristics of the method are reflected in the claims.

The invention is based on the idea that the capital cost of the enterprise to obtain stanulovic esters can be significantly reduced if lower stages of crystallization and filtration of the crystalline intermediate compounds containing stanol, from the reaction mixture, when the solvent hydrogenation process is left in the reaction solution, which was removed the catalytic hydrogenation. If necessary, the solvent is about the ECCA interesterification and solvent for the process of interesterification, if any.

It is preferable, however, that the solvent used in the hydrogenation process was used not only as a solvent but also as a reagent in the process of interesterification.

In the case when stanol formed as an intermediate product in the reaction of hydrogenation, is not separated from the reaction mixture before the step of transesterification, then reached not only the lowering of capital costs, but also an almost quantitative yield of the final product, as it eliminates the loss of output that would otherwise be inevitable at intermediate separation and filtration of the crystalline intermediate product.

In a particularly preferred embodiment of the present invention as a reagent process of interesterification and, perhaps as a solvent for the hydrogenation process using methyl ester of fatty acids derived from vegetable oils. Especially advantageous to use for the process of hydrogenation solvent having a lower boiling point than the reagent interesterification process; in this case, the solvent for the hydrogenation process may be removed by distillation from the reaction RA is shown adding saturated fatty acids to the final product stanovova ether. In this case, the solvent used for the hydrogenation process is preferably the methyl ester of coconut fatty acids or fatty acids of palm oil, while the reagent process of interesterification is a methyl ester of fatty acids of rapeseed oil. The source of fatty acid or composition of fatty acids in the ester alcohol, which is used as the reactant of the process of interesterification can be fatty acids of any grease, oil or composition.

Stanolone esters can indeed be obtained according to the invention, without crystallization and separation of Stanlow, also using conventional solvents for the hydrogenation process instead of the methyl esters of fatty acids. In this case, suitable solvents are alcohols, hydrocarbons and ethers of the type of tetrahydrofuran. Especially advantageously used as the solvent for the hydrogenation process of the high-boiling non-aromatic and therefore inert aliphatic hydrocarbon, because it does not interact with the chemical process of transesterification on the stage interesterification. This alternative solution is more preferable in the case where it is desirable to prevent including olshey in the process of interesterification, add to the reaction mixture remaining after hydrogenation and from which the separated catalyst for hydrogenation, and then before the actual process of transesterification is removed by distillation of the solvent for the hydrogenation process. However, the use of methyl esters of fatty acids can be justified because they have a higher flash point than conventional solvent-type n-propanol, which provides better fire safety.

The hydrogenation catalyst is preferably a catalyst based on a noble metal, such as palladium on coal or organic polymer compound. The process of hydrogenation is preferably carried out at a temperature not exceeding 120oBut the hydrogen pressure can vary over a wide range. The amount of hydrogenation catalyst used in the reaction, may also be different, but it is preferable to use the active ingredient in an amount of 0.1-2% by weight of Sterol, which must be subjected to hydrogenation. When using these process conditions of the hydrogenation the hydrogenation process can be carried out at high concentrations of solids, quickly and without process hydrogenation removed by filtering the hot reaction mixture. Filtration of the hydrogenation catalyst is a simple process and does not require high costs.

As a catalyst for interesterification process preferably uses the alcoholate of an alkali metal, such as methylate or sodium ethylate. In this case, the amount of catalyst in the process of interesterification is 0.1-1% by weight of the reaction solution. The process of transesterification is carried out at 100-130oAnd when using a stoichiometric excess of the reagent of the process of transesterification, for example double excess relative to stanol or Stanovoy composition.

According to the invention, in the method as starting substances can be used any Sterol or Sterol composition of vegetable origin, and in principle also animal sterols, such as cholesterol and lanosterol. However, it is preferable that gidriruemyi composition of the sterols contained mainly sitosterol and additionally campesterol and possibly stigmasterol. Particularly preferably, gidriruemyi mixture of sterols was based on tallow or vegetable oil.

Unexpected is that even if you omit necessary from the standpoint of prior known is his stanol, and removing the crystals by filtration, the resulting product stanovova ether nevertheless can be obtained in a sufficiently pure state and, above all, with a higher yield when using the cleanup stage of pereeterifikacii, which is in itself known. Even if the impurity concentration (for example, products of the dehydrogenation of Tocopherols and sterols, hydrocarbons with a long chain of carbon atoms, and fatty alcohols) formed in the reaction and bring the raw materials were high enough, then, according to the invention, it is possible to remove them using a known method, for example by distillation with water vapor and adsorption. In addition to these treatment processes can also be used, for example, the process of thin-film evaporation.

In the first stage, carried out a series of reactions - stage hydrogenation, preferably using such catalysts as catalysts containing precious metals: palladium, platinum or ruthenium. It is also possible, for example, the use of Raney Nickel, cobalt, or magnochromite catalysts. The catalyst carrier may be, for example, carbon, alumina, silica or organic polymer carrier.

the Noah mixture can vary within very wide limits. The concentration of catalyst may vary within wide limits. By maintaining the temperature above the level of the most effectively avoid the formation of by-products (for example, the reaction of removal of hydroxyl).

Thus, with proper selection of the conditions of the hydrogenation the hydrogenation process can be performed at high concentration of dry matter, quickly and without the formation of harmful by-products.

Before the end of the reaction the hydrogenation catalyst in the hydrogenation process are removed from the reaction mixture by filtration. If before transesterification desirable to remove part of the solvent hydrogenation process (methyl ester or other similar solvent), it should be conducted at a later stage. This is done by adding to the reaction mixture of methyl fatty acid ester, which must be used in the interesterification process, before or after distillation. Conditions of carrying out the process of distillation of the solvent, of course, depend on the physical properties of the used solvent. When this desirable condition is that the boiling point of the solvent on the fatty acid, used as a reagent, in order to ensure the possibility of fractional removal of the solvent hydrogenation process.

The next step of receiving stanovova ether is the stage of interesterification of stanol with ether fatty acid contained in the reaction solution.

The esterification reaction essentially can come under the influence of any reagent that catalyzes the transesterification (e.g., inorganic acids, toluensulfonate, organic tin compounds or alkaline catalysts). However, especially preferably used in the process of interesterification of alkali metal alcoholate, such as methylate or ethylate sodium - interesterification catalysts, which are in themselves known from the literature. The concentration of the catalyst and other reaction conditions vary widely depending on the type of catalyst. In the reaction using sodium methylate it is desirable to use the catalyst in an amount of about 0.1 to 1% of the number of the reaction mixture. When 100-130oC for 60-180 min the reaction takes place completely at about double the stoichiometric excess of methyl ester of fatty acid relative and formed in the reaction and introduced with the feedstock impurities (catalyst, the decomposition products of Sterol and others ) can be removed by washing with water and distilling with steam, and optionally, if necessary, by absorption of impurities suitable absorption material (e.g., containing activated charcoal and/or whitening the ground). Distillation with steam is a necessary step cleaning and to remove any excess reagent. Suitable conditions stage distillation using methyl ester of rapeseed fatty acid as solvent are: a temperature of 180-230oWith the pressures of 0.1-1 kPa and the amount of steam applied approximately 2-10% of the total number of the reaction mixture.

The following are examples of ways to obtain stanulovic esters according to the invention.

EXAMPLE 1. 300 g of Sterol derived from tall oil (10% campesterol/stanol, 90% -sitosterol/stanol) were suspended in 700 g of methyl ester of coconut fatty acid (containing esters of fatty acids, mainly WITH6- C14). Pd catalyst deposited on a fibrous polypropylene, Smop-20 (produced by Stoptech, Turku, Finland) was added in the amount of 0.7% of the amount of Sterol, the temperature was raised to 120oC, and the reaction autoclave byvania pressure in the reaction mixture varied in the range of 1-2 ATM. The hydrogenation catalyst was removed from the hot reaction medium by filtration. After that, the reaction mixture is introduced 360 g of methyl ester of fatty acids of rapeseed oil, and added as a solvent methyl ester of coconut fatty acid was removed by distillation at 140oC and a pressure of 0.8 kPa. Then as interesterification catalyst was added 3 g of sodium methylate, and the process of interesterification was carried out at 120oC for 5 h under a pressure of 0.5 kPa. The resulting ether was washed twice with water, and excess methylating reagent and impurities were distilled with steam at 200oC and 0.3 kPa. The product was filtered through whitening earth and a layer of activated charcoal. Received the product on the basis of stanovova ether contained 0.02% of free fatty acids, 0.3% methyl esters of fatty acids, and 0.8% not subjected to esterification sterelny compounds. According to the method of DSC (differential scanning calorimetry), the melting point of the ester stanol was 36-39oWITH

EXAMPLE 2. 295 g of Sterol derived from vegetable oil (25% campesterol, 55% -sitosterol and 15% of stigmasterol) were suspended in 705 g of methyl ester of coconut fatty acids (cotogna media 0.2% of palladium on the number of Sterol), the temperature was raised to 120oC. the Reaction the autoclave was purged with nitrogen. After that, the nitrogen was replaced by hydrogen atmosphere, the hydrogen was admitted to the reaction mixture in the course of 110 minutes During the hydrogenation pressure of hydrogen in the reaction mixture was 1-2 ATM.

The hydrogenation catalyst was removed from the reaction mixture by filtration.

Thereafter, 3 g of sodium methylate was added as a catalyst for esterification, the esterification reaction proceeded at 125oC for 1.5 h under a pressure of 0.7 to 0.9 kPa, at this time was removed, the formed methanol. Essential product in the first stage was distilleria with steam at 140-145oC and 0.7 to 0.9 kPa. In conclusion, the temperature was raised to 200-205o(Pressure of 0.3-0.4 kPa) to remove high boiling impurities. The resulting product was filtered through whitening earth and a layer of activated charcoal. Received the product on the basis of stanovova ether contained 0.025% of free fatty acids, 0.3% methyl esters of fatty acids, 0,6% not subjected to esterification sterelny compounds. The melting point stanovova ether was 93-97oWith the method according to DSC.

EXAMPLE 3. In the of varicella for the hydrogenation process and at the same time he was used as a reagent process of esterification instead of the methyl ester of coconut fatty acids. Stages of interactions and purification were carried out according to example 2 (however, the temperature and the pressure during the distillation with water vapor was 200-205oWith/0,3-0,4 kPa). The obtained plastic product had a melting point in the range 98-104oC.

EXAMPLE 4. In this example, the solvent used for the hydrogenation process was the methyl ester of coconut fatty acids, which before the step of transesterification was partially removed by distillation with water vapor and replaced by a methyl ester of fatty acids of rapeseed oil.

250 g of Sterol derived from vegetable oils, were suspended in 650 g of methyl ester of coconut fatty acids. The Pd/C catalyst was added in an amount of 0.2%, and the hydrogenation process Sterol was carried out as in the previous examples.

The hydrogenation catalyst was removed from the reaction mixture by filtration.

Thereafter, 300 g of methyl ester of fatty acids of rapeseed oil was sent to the reaction mixture, a saturated ester of coconut fatty acids was distilleria at 140-150oC and 0.7 to 0.9 kPa. The mixture was subjected to interesterification and purified by the methods set forth in the previous examples. Received the plastic is under way, described in example 1, high-boiling aliphatic hydrocarbons (temperature range distillation 180-210o(C) free from aromatic compounds, was used as a solvent for the hydrogenation process instead of the ester of coconut fatty acids. The interaction processes and purification were carried out according to example 1. The resulting product was a plastic mass, corresponding to the product in example 1 and having a melting point in the range of 37-40oC.

1. The method of obtaining stanulovic esters by hydrogenation of at least one Sterol in the solvent and at elevated temperature in the presence of a hydrogenation catalyst with the formation of at least one stanol, with the subsequent removal of the hydrogenation catalyst from the obtained reaction solution, followed by the process of transesterification of at least one of the specified stanol with ether containing lower alkyl, at elevated temperature and in the presence of an interesterification catalyst and subsequent treatment thus obtained stanovova ether or song stanulovic esters, characterized in that the solvent for the hydrogenation process are left in the reaction of races is greater least partially replace chemical interesterification and/or b) used as solvent for the process of interesterification and preferably at the same time as the reactant of the process of interesterification.

2. The method according to p. 1, characterized in that the reagent of the interesterification process and, as a solvent for the hydrogenation process using methyl ester of fatty acids derived from vegetable oils.

3. The method according to p. 2, characterized in that the solvent for the hydrogenation process is more low-boiling than the reagent process of interesterification, and it is removed by fractional distillation from the reaction solution, in which at the same time or earlier, add the reagent to the process of interesterification.

4. The method according to p. 3, characterized in that the solvent for the hydrogenation process using methyl ester of coconut fatty acids, and as a reagent in the process of interesterification methyl ether fatty acids of rapeseed oil.

5. The method according to p. 1, characterized in that the solvent for the hydrogenation process and at the same time as solvent for the process of interesterification use alcohol or high-boiling aliphatic hydrocarbon, free from aromatic compounds.

6. The method according to any of the preceding paragraphs, characterized in that the hydrogenation catalyst is used catalisano.

7. The method according to p. 6. characterized in that the hydrogenation catalyst is used in an amount of 0.1 to 2.0% by weight of the active component of the Sterol subject to hydrogenation.

8. The method according to any of the preceding paragraphs, characterized in that the hydrogenation process is carried out at a temperature not exceeding about 120oAnd the hydrogenation catalyst is removed from the reaction solution, preferably by filtration.

9. The method according to any of the preceding paragraphs, characterized in that as a catalyst for interesterification use alcoholate of an alkali metal, preferably methylate or sodium ethylate.

10. The method according to p. 9, wherein the interesterification catalyst is used in an amount of 0.1 to 1.0% by weight of the reaction solution.

11. The method according to any of the preceding paragraphs, characterized in that the process of interesterification is carried out at 100-130oAnd when using a stoichiometric excess of the reagent process of interesterification on stanol or composition of Stanlow.

12. The method according to any of the preceding paragraphs, characterized in that the composition of sterols, subject to hydrogenation, consists mainly of sitosterol and additionally from campesterol hydrogenation, are derived from tallow or vegetable oil.

 

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