The method of obtaining sitosterol from tall oil pitch


(57) Abstract:

The invention relates to a method for sitosterol from tall oil pitch. Sitosterol obtained from vegetable raw materials, can be used in chemical, pulp and paper, food, pharmaceutical and other industries. The method consists in the following: tall pitch pine wood omelet alkaline, followed by extraction spirtobenzinovoy mixture with a ratio of alcohol : petrol 1:12 - 1:20 at 25-35oWith and release of the target product by crystallization solution of ethyl acetate containing 5-8% water, 5-15oS. the Method of obtaining sitosterol from tall oil pitch simple to perform, requires no special equipment, can significantly improve the quality of the finished product. The method was verified in a pilot scale in OJSC "Lesosibirsk KAS". table 1.

The present invention relates and obtaining sitosterol from vegetable raw materials and can be used in chemical, pulp and paper, food, pharmaceutical and other industries.

The main focus of sitosterol is the manufacture of preventive drugs Digene cardiovascular disease), and also as raw material for drug synthesis hormonal means, the first stage of which is microbiological oxidation Androstenedione.

For these purposes, as follows from the total accumulated world experience, fit obtained from vegetable raw materials sitosterol (the so-called phytosterol) a well-defined composition, namely:

for ingestion (dietary Supplement) - mass fraction of transforming sterols should not be less than 95% -sitosterol as a main component is 75-85%; -sitostanol - 10-15%; campestrin - 6 - 10%; campestanol - 2-5%. Pets presence of related cyclic and acyclic alcohols nonsteroidal nature;

for the synthesis of hormones share the transforming of sterols must be at least 80-85%.

When this prerequisite is the absence sitosterol is not for these purposes-sitosterol and Betulinol is most often present in the phytosterol related transformable sterols components.

From the available raw materials of plant origin are the most rich in sterols sulphate soap by-product upon receipt of cellulose sulfate way from wood and tall oil pitch - p is erenow) of these raw materials. They have a number of common characteristics. The hallmark of ways to get phytosterol from tall oil pitch from the methods of its production from sulfate soap is the introduction of an additional stage of saponification of tall oil pitch with alkali. All these known methods for producing phytosterol (mixture of sterols from tall oil products can be divided into two groups:

- crystallization of the neutral components of the aqueous-alcoholic solutions of soap (sulphate or pitch after saponification);

extraction of the neutral components of the soap organic solvent, followed by separation of phytosterol from neutral substances by crystallization.

Methods for producing phytosterol crystallization of alcohol-water solutions of Soaps have a number of technical and technological disadvantages, and the obtained product contains, in addition to sterols, salts of fatty and resin acids, which causes the need for additional purification and leads to a significant reduction of output. Get ways phytosterol has a limited scope, and methods do not allow to obtain a product of desired composition.

Extraction methods for isolating sterols from tall oil products have several advantages. Known naprelan substances with ethyl acetate, the distillation of ethyl acetate is added to the content in the extract is not more than 4%, one stripped off the extract is dissolved in the alcohol-gasoline mixture, taken in a mass ratio of 0.5-1.5:1, washed with water, then alcohol-gasoline solution of neutral substances evaporated. From the obtained after evaporation of the concentrate neutral substances by crystallization from ethanol-sitosterol with a melting point 134oC. This method has several significant disadvantages. The use of ethyl acetate as a solvent leads to its saponification in an alkaline medium and, consequently, the accumulation of acetic acid (and alcohol). In addition, because the solubility of ethyl acetate in water (up to 8%) in the extract are salts of fatty and resin acids, and in the aqueous phase after settling together with ethyl acetate neutral substances. This circumstance on the one hand leads to contamination of sterols and the need for additional purification, and, on the other hand, due to the receipt of the extractant in the aqueous phase is ash with him neutral substances, resulting in lower output sitosterol, as well as water pollution and occurs as a consequence of environmental complications.

The main disadvantage of this and other well-known ways is about the main directions of the use of quality therefore, the magnitude of the output product. Here is the assessment of the quality of the product at its melting temperature, is necessary but not sufficient characteristic of the received sitosterol. It is known that the melting temperature-sitosterol is 140oC. it is also Known that when the receiving-sitosterol from vegetable raw materials along with him retrieves related sterols were present in the raw material alcohols, melting point above 140o(-sitosterol - 165-167oC, campestrin - 158oC, Betulinol - 253oC) and below 140oC (the melting point of artenara, for example, 115oC). Therefore, pokazatel - melting point - not able to characterize the composition obtained-sitosterol or phytosterol and, accordingly, is not pokazatelem characterizing the suitability of the product and its compliance with the required quality.

A known method of producing phytosterol from tall oil pitch by saponification with alkali in alcohol medium by heating with subsequent isolation of the target product. The method involves the use of alcoholic phase propanol with the introduction of the additive of aluminum oxide in an amount of 0.1 to 1.0 wt.% from peck. The ratio of pitch and propanol 1:(5-10) parts p the NCI solvent stylenny peck processed (extracted) in diethyl ether and the solvent (ether) drove away. For crystallization of the phytosterol concentrate neutral substances (the product after distillation of the solvent (ether) used ethanol. This method also has its disadvantages. Despite the high yield of sterols (phytosterol), confirmed the possibility of obtaining the product of desired quality. The use of diethyl ether as a solvent leads to high explosive and fire risk process, and the use of aluminum oxide leads to environmental complications associated with the treatment of wastewater from metal.

Also known is a method of obtaining sitosterol from tall oil pitch, including two-stage saponification tall oil pitch, followed by separation sitosterol by crystallization from water-alcohol solution pitch soap. This way inherent in the above-mentioned disadvantages of crystallization methods for producing phytosterols.

Closest to the proposed method for the extraction of phytosterol from waste Kraft pulp production (prototype), which consists in the following. Waste from processing selfaccelerating production - tall oil pitch is subjected to saponification and subsequent extraction of phytosterol gasoline and crystallization of the residue after removal of the Colo 30%, esters of 4-6%, aldehydes - 8%. After 3-fold recrystallization of the obtained (according to the authors - -sitosterol) product with a melting point 132-134oC and output 3-4% of the original pitch. This known method of obtaining sterols, taken as a prototype, also has a number of disadvantages.

First, in this way, as in other known methods, confirmed the possibility of obtaining the target product - -sitosterol required quality. Secondly, the use of gasoline as a solvent neutral substances causes a considerable complication for phase separation of organic and aqueous layers due to the formation of a stable emulsion of the type water-in-oil. It is known that-sitosterol and its corresponding sterols are effective emulsifiers and emulsion stabilizers. Due to the emulsification is hit salts of resin and fatty acids in the organic layer, and neutral substances in the water layer. This circumstance leads to deterioration of product quality (need three crystallization for purification) and loss of neutral substances that remain in the pitch soap.

The aim of the proposed method is to simplify the technology and getting sitosterol is A.

This objective is achieved in that tall peck coniferous trees omelet alkali in a known manner, the extraction of neutral substances lead from diluted with water pitch soap mixture gasoline nefras) and alcohol (ratio of alcohol : petrol from 1:12 to 1:20), and obtaining the target product - sitosterol desired composition and quality - by crystallization at a temperature of 5-15oC concentrate neutral substances (CNV) obtained after removal of the solvent from the extract, watered by ethyl acetate containing 5-8% water.

The following are examples to illustrate the proposed method.

Example 1. 100 g of tall oil pitch obtained after distillation of tall oil from pine wood in Ust-Ilimsk content neutral substances 29.8 wt.% omelet standard method, of 40% aqueous sodium hydroxide. The obtained pitch soap diluted with water (1 part soap to 3 parts water) and extracted with spirtobenzinovoy mixture (1 part isopropyl alcohol and 12 parts of gasoline Nefras 80/120). For this to 420 g of the obtained solution of soap add 2730 g of extractant and the mixture was thoroughly stirred for 2 h at 30oC. after stirring the mixture advocate for 2.5 h Ave the creation of neutral substances in gasoline, separated and evaporated to remove the solvent. The rest is a concentrate of neutral substances (CNV). 2300 g of the extract obtained by 26.8 g CNV.

Received knw dissolved in 134 g watery ethyl acetate (5% water), and the mixture was stirred at 75-80oC until complete dissolution CNV. After that, the solution is cooled to a temperature of 10oC and crystallization at this temperature for 7-8 hours the Precipitated crystals sitosterol is separated by filtration, washed with watered with ethyl acetate, then with water and dried.

Obtained 4.8 g of sterols with a mass fraction of transformed sterols of 82.6% and a melting point 122oC.

Chemical composition (GLC), wt.% -sitosterol (sitostanol) was 74.3; campestrin (and campestanol) - 8,3; cyclic and acyclic alcohols - 17, an impurity is 0.4. -sitosterol - UTS., Betulinol - UTS.

The output of 4.8% from peck.

Example 2. Same as in example 1, 420 g of the solution pitch soap extracted 4910 g spirtobenzinovoy mixture. From 3970 g of the extract obtained 27.5 g CNV.

Crystallization knw lead from watery ethyl acetate (8% water) at the 5oC.

Received: 5,2 g sitosterol with a mass fraction of transformed sterols 84 - 5,8: campestrin (and campestanol) - 8,7, cyclic and acyclic alcohols - 15,2: impurity - 0,3; -sitosterol - UTS.. Betulinol - UTS.

The yield of 5.2%.

Example 7 (semi-industrial). 1000 kg of tall oil pitch obtained after distillation of tall oil from pine trees at the Ust-Ilimsk, with a mass fraction of neutral substances 30,6% are placed in a reactor equipped with a jacket for heating, a stirrer and a reflux-condenser. There also add a 42% solution of caustic soda in the number 626 kg

The process of saponification is carried out at constant stirring of the mixture at 100-105oC for 5 hours Upon completion of the saponification there is added under stirring 2635 kg of water. From the thus obtained aqueous solution pitch soap extract neutral substances by extraction with a mixture of isopropyl alcohol and gasoline in the ratio of 1:12. The process of extraction of the lead portions 35oC. 4261 kg solution pitch soap was spent 27300 kg extractant and received 24500 kg of the extract, after evaporation of the extractant selected 285 kg of concentrate unsaponifiable substances (output - 93% of theoretical).

Received knw dissolved in 1425 kg watery ethyl acetate (5% water), and is litre, washed with ethyl acetate, water and dried.

Received: 45 kg sitosterol with a mass fraction of transformed sterols 81% and a melting point of 120oC. the Chemical composition of sitosterol (GC), mass. %: -sitosterol (sitostanol) - 74; campestrin (and campestanol) - 7,0; acyclic and cyclic alcohols to 18.7; impurities - 0,3: -sitosterol - OTS.; Betulinol - UTS.

O.- 4.5% of the pitch.

Example 8. 100 g of sitosterol obtained in example 7, is dissolved in 1000 g watery ethyl acetate (8% water) at 75-80oC. the resulting solution was cooled to 25oC and lead the process of crystallization for 6 h at this temperature. The precipitated crystals are separated by filtration, washed with ethyl acetate, water and dried.

Received: 84,2 sitosterol and mass fractions of transformed sterols 96,1% and a melting point of 133oC.

Chemical composition (GC), mass. % - -sitosterin (sitostanol) - 86,3, campestrin (and campestanol) - 9,8 cyclic and acyclic alcohols and 3.5, impurity - 0,4; -sitosterol - OTS.; Betulinol - UTS.

The output of 3.8% from the original pitch.

The given examples show that the proposed method in the present limits of the parameters of the process ensures the obtaining of and quality namely, the mass fraction of transformed sterols 80-95% with no harmful impurities-sitosterol and Betulinol.

The process of extraction of neutral substances from the pitch at a temperature above the claimed increase the speed of the process, however, is undesirable because it increases the solubility of salts of acids, which leads to deterioration of the quality and reduce the yield of the target product as a consequence of the need to introduce additional stages of purification of the extract and of the finished product. In addition, the temperature of doing the extraction process is impractical because of energy considerations. The process of extraction at a temperature below the declared undesirable for reasons of mass transfer, but also because of the possibility of premature precipitation of crystals of the target product from the extract.

The presence of the alcohol extractant is required because, in the absence of complications due to the formation of stable nerastraivaisya emulsion extractant (petrol)-water, and as a consequence, the loss of the target product, solvents, and the impossibility of doing process (see, in particular, example 4). The use of an extractant containing alcohol in coldshine quality of the finished product and decreasing output. In addition, increased consumption of alcohol is undesirable because of economic considerations.

Use during crystallization sitosterol "watery" ethyl acetate can significantly improve the quality of the finished product (see, in particular, example 6). The increase in the share of water in ethyl acetate impossible because of the limited solubility of water in ethyl acetate.

The proposed method for sitosterol from tall oil pitch is relatively simple in execution, which does not require special equipment. He tested at pilot scale in OJSC "Lesosibirsk KAS' (, Lesosibirsk, Krasnoyarsk region), where 1 t tall oil pitch U. Rimskogo LPK (, Ust-Ilimsk, Irkutsk region) received 45 kg sitosterol, fully meet the chemical composition requirements of the microbiological industry.

The resulting product was tested in pilot conditions ZAO Pendaftar" in Moscow), where the desired output was obtained androstenediol microbiological oxidation. Method of microbiological oxidation of sterols in Androstenedione is also of practical importance, a reliable test of the quality of sterols, as PR is also inhibition of the oxidation process.

Implementation of the proposed method will allow for the first time in Russia to create on the basis of available and relatively cheap raw materials production sitosterol and hormonal drugs with a broad spectrum of action, as well as food additives, having hypocholesterolemic activity, to regulate cholesterol in the blood and, thereby, reduce cardiovascular disease.

The method of obtaining sitosterol from tall oil pitch by saponification with alkali, followed by removing by extraction with an organic solvent and isolation of the target product by crystallization, characterized in that the extraction process saponified tall oil pitch coniferous trees are spirtobenzinovoy mixture with a ratio of alcohol : petrol 1 : 12 - 1 : 20 at 25 - 35oC, crystallization was extracted from coal tar neutral substances lead after removal of the extractant solution of ethyl acetate containing 5% to 8% of water, with 5 - 15oC.


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