Method of dihydroquercetin production

FIELD: medicine; pharmacology.

SUBSTANCE: wood of Siberian or Daurian larch is debarked, cleaved and dried at 40-50°C to residual moisture 23-27%. Dried wood is chopped, and soluble substances are extracted with 75-85% ethyl alcohol aqueous solution at temperature 45-50°C in ratio raw material:extracting agent 1:(7-10). Further extracting agent is distilled off, and sawdust is supplied to press for additional alcohol return. Then extract aqueous part is cooled to 20-25°C within 20-30 minutes for isolation of resinous impurity accompanying dihydroquercetin (DHQ). Deresined extract aqueous part is added with methyltertbutyl ether (MTBE) in ratio 1: (0.3-0.45), and DHQ is reextracted within 2-3 hours. Extract ether part is isolated separate from aqueous part through sedimentation within 2-2.5 hours and supplied to MTBE evaporation, while target product is crystallised of hot water. Invention enables to produce DHQ with yield 2.2-2.5% of bone-dry wood mass with grade 90-96%.

EFFECT: simplification of process and production of high-quality product.

4 cl, 2 ex

 

The invention relates to chemical-pharmaceutical industry and relates to improvements in the method of producing dihydroquercetin (DQC).

It is known that the DQC has antioxidant, angioprotective, regenerating, detoxifying, anti-edematous action, has the ability to restore the elasticity of blood capillaries, prevents inflammatory processes, opukholeobrazovanie etc. due To the wide use of the DQC in the food, medical, cosmetic industries, the task of developing improved methods of its production remains relevant.

There are various methods of processing wood and bark of larch to obtain a wide range of biologically active products for food industry and medicine (V.A. Babkin, Ostroukhova L.A., Ivanova SZ and other Products for deep chemical processing of biomass larch. Grew up with. chem. J., 2004, .XLVIII, No.3, pp.62-69). The main active ingredient derived drugs is dihydroquercetin (DQC) is a flavonoid natural origin with a wide spectrum of biological activity.

All known methods of chemical processing softwood trees can be divided into three groups:

1) the ways that obtains a water-soluble products through education is otci feedstock with aqueous solutions of electrolytes;

2) methods involving obtaining navodno-soluble products of biologically active compounds, natural resinous substances - materials processing organic compounds (solvents);

3) methods involving obtaining cellulose materials processing alkalis and acids.

However, existing methods of obtaining these products are characterized by low use of wood (about 20-30%).

Known, for example, the allocation method DQC from larch wood by extraction of water by heating, cooling, filtering and mixing an aqueous extract for 2 h with polyamide powder in the ratio of 1:10, filtering off and drying polyamide powder, extraction DQC with polyamide powder with ethyl acetate and subsequent crystallization him out of hot water. (Patent RF № 2000797, CL AC 35/78, 1993).

The main disadvantage of this method is the low yield of the target product and the duration of the method.

A method of obtaining DQC by first removing water-soluble substances in the washing sawdust larch wood with water at ordinary temperature, followed by extraction DQC a mixture of water-acetone (1:4) at ordinary temperature. Dropped out after distillation of the acetone from the aqueous portion of the extract sieges is to DQC is recrystallized from hot water. Purity DQC is 95-97%, the yield of 1.75 to 2.0% by weight of absolutely dry wood (ASD) (RF Patent N 2038094, CL AC 35/78, publ. 27.06.95).

The disadvantages of this method are the duration of the process due to the implementation stage of the preliminary washing of sawdust with water, yield DQC due to losses during washing, sawdust, water, and huge consumption of expensive solvent is acetone, which because of its unlimited solubility in water is difficult regeneration.

A method of obtaining dihydroquercetin, including extraction of crushed wood of coniferous breeds by heating, filtration of the extract, its evaporation, extraction of the target product, its crystallization from hot water and drying, characterized in that as softwood use larch or douglasawh fir, the extraction was performed with ethyl acetate for 1-5 h at a ratio of crushed wood of larch or douglasawh fir and ethyl acetate 1:(5-7), and removing the desired product from one stripped off of the extract is carried out with hexane or gasoline at a ratio of 1:(8-20), and the process of extracting the target product is carried out at a temperature of 18-24°C for 15-40 min and stirring, after which hexane or benzene is distilled off. The purity of the target product is 94-96%, output Digi is requiredin 0.9 to 1.0% by weight of absolutely dry wood (RF Patent No. 2082425, CL AC 35/78, publ. 27.06.1997).

The disadvantages of this method are the high consumption of organic reagents and low yield of the target product.

A method of obtaining DQC from crushed wood of larch, including pre-impregnation of the latter with water (at a temperature of 25-40°C), extraction with ethyl acetate (ratio of raw material:solvent 1:4), evaporation of the extract and handling of gasoline (or hexane) without heating to remove tar. Not the extract is treated with hot water (temperature of 95-98°C), filtered from impurities. Upon cooling of the aqueous solution falls crystals DQC. The purity of the product is 90-95%, the output DQC of the mass of absolutely dry wood 1% (RF Patent No. 2158598, CL AC 35/78, publ. 10.11.2000).

The main disadvantages of this method are the high consumption of organic extractants (gasoline and ethyl acetate), and correspondingly high consumption of electricity for their evaporation and heating of the extraction and the low yield of the target product.

The most closest to the claimed method prototype is a method for dihydroquercetin, comprising the following stages (RF Patent No. 2034559, AK 35/78, publ. 10.05.1995,).

The crushed and dried the wood of larch (relative humidity 7%) fill in n-hexane or petrol and boil with bratim refrigerator for 1 hour. The solvent is then drained, and not sawdust poured with ethyl acetate, heated to the boiling point (77° (C) and refluxed for one hour. The hot extract was filtered from sawdust, cooled and evaporated. Dry extract pour hot water (ratio 1:10, 80° (C) and allocate dihydroquercetin by crystallization from hot water. The output of dihydroquercetin is 0.81-0,91 of the mass of absolutely dry wood, the purity of the target product is 92-96%.

The disadvantages of this method are the duration of the process and low yield of the target product.

An object of the invention is to increase the yield of the target product, while maintaining its high quality.

The goal of the project is achieved by the proposed method lies in the following.

The wood of Siberian larch or white-naped peeled from the bark, split and dried at 40-50°C to a residual moisture content of 23 to 27%. Dried wood is crushed and loaded into the extractor. From crushed wood of larch extracted soluble substance in an aqueous solution of ethyl alcohol containing organic part of at least 75%, mainly 75-85% (azeotropic mixture ethanol-water)at a temperature of 45-50°when the ratio of raw material:solvent 1:(7-10). Next, the solvent is distilled off, and the files with the rest of the extractant serves to press for an additional refund of alcohol. Then the aqueous portion of the extract is cooled to 20-25°C for 20-30 minutes to remove related DQC resinous impurities.

In deresinated aqueous portion of the extract (concentrate) add metyltrebutyl ether (MTBE) in the ratio 1:(0,3-0,45) and extravert DQC at a temperature of 34-36°C in vacuum for 2-3 hours. Essential part of the extract is separated from the water portion of the defense for 2-2,5 hours and served on evaporation. After evaporation of the ether fraction to the dry residue add distilled water, heated aqueous solution containing DQC, up to 50°and crystallized With the last of the hot water.

The proposed method allows to obtain DQC with the release of 2.2-2.5% of the mass of absolutely dry wood with purity of 90-96%. The chemical composition of the DQC proven methods of elemental analysis of C, H, O and high performance liquid chromatography HPLC.

Determining the distinctive features of the proposed method in comparison with the prototype are:

1. The extraction of raw materials carry 75-85% ethanol at a temperature of 45-50°when the ratio of raw material:solvent = 1:(7-10), which allows to significantly simplify the process, to exclude from the process stage preliminary removal of resin crushed wood nonpolar hydrocarbons (n-hexane or petrol), to make the process is economical and more profitable as the temperature of the wood is reduced to 45-50°C.

2. The resulting aqueous portion of the extract (after separation of the extractant) refrigerate for 20-30 minutes to 20-25°for deposition of resinous impurities, which improves the purity of the target product.

3. From deresinated extract is re-extracted with DQC methyl tertiary butyl ether at a ratio of 1:(0,3-0,45) within 2-3 hours, allowing you to further purify the desired product from the impurities of resins and oils.

Methyl tertiary butyl ether has valuable qualities and cheap. It is favorable for the process boiling point /52°With almost does not dissolve water and other polar substances and very well soluble organic compounds of medium polarity, which is the DQC. It is very important that metyltrebutyl ether unlike known for this process, ether solvents such as diethyl ether, dioxane, tetrahydrofuran, bad form peroxides and therefore more preferable in the aspect of the explosion.

The invention is illustrated by the following examples of specific implementation method.

Example 1.

The Siberian larch wood peeled from the bark, split and dried at 50°C to a residual moisture content of 23%. Dried wood is ground first at chipping machine MRR-20 to which the sizes of wood chips, then to a particle size of 1×0,1×1 mm on the blade grinder and loaded into the extractor with a working volume of 6 cubic meters

450 kg of crushed wood of larch pour 3465 liters of 75% aqueous ethanol solution (the ratio of raw materials - extractant 1:10) and the extraction is carried out at a temperature of 50°and With constant stirring for 3 hours. Next, aqueous-alcoholic extract served in a vacuum evaporation apparatus, and sawdust screw conveyor, with the remainder of the extract is fed to a screw press AMPS-01, where additionally carry out the extraction of the extract, which also served on evaporation in a vacuum evaporation apparatus. The remaining mass of wood fed to the granulator PG-310 for receiving fuel pallets.

Distilled alcohol is returned to the process cycle, and the aqueous portion of the extract (concentrate) is poured into a container of "shirt", cooled for 30 min to 20°when this occurs, the deposition of the resin on the bottom of the tank, which is removed manually with a spatula.

Deresinated concentrate (220 liters) is pumped into a tank for holding essential Stripping, add 100 liters of methyl tertiary butyl ether and extravert DQC in the vacuum of 0.2 MPa with stirring (pumping pump in a closed circle) at a temperature of 36°C for 2 hours. Next essential part of the extract is separated from the water portion of the defense during the course the e 2.5 hours, the water is drained, and the ether fraction containing DQC (95 liters), served on evaporation.

After evaporation of the ether fraction to the dry residue add distilled water (190 liters), heated aqueous solution containing DQC, up to 50°and poured into the container, where the target product is crystallized by cooling water from 50 to 18°C for 2 hours. Then DQC is filtered on Buchner funnels filter paper and then the target product with a humidity of 45% is dried in an oven at a temperature of 50° to a residual moisture content of 7%.

The output of the DQC was 2.2% by weight of absolutely dry wood with a degree of purity of 94%.

Example 2

The Daurian larch wood peeled from the bark, split and dried at 40°C to a residual moisture content of 27%. Dried wood is ground first at chipping machine MRR-20 to the size of wood chips, then to a particle size of 1×0,1×1 mm on the blade grinder and loaded into the extractor. 450 kg of crushed wood of larch extracted soluble substances 85%aqueous solution of ethyl alcohol at a temperature of 45°when the ratio of raw materials - the extractant is 1:7 (2300 l)with constant stirring for 2 hours. Upon completion of the extraction pump out water-alcohol extract of vacuum pump and is served in a vacuum evaporation apparatus for the distillation of alcohol and sawdust from OST the com extract serves to press. Obtained by distillation of the alcohol back into the production cycle, and the aqueous concentrate is poured into a container of "shirt", cooled for 20 min to 25°when this occurs, the deposition of the resin on the bottom of the tank, which is removed manually with a spatula.

300 l not concentrate add 100 l metyltrebutyl ether and extravert DQC under stirring at a temperature of 34°in the vacuum of 0.2 MPa for 3 hours, after which MTBE is separated from the water portion of the defense for 2 hours, water is drained, and the ether fraction containing DQC (95 liters), served on evaporation.

After evaporation of the ether fraction to the dry residue add distilled water (240 liters), heated aqueous solution containing DQC, up to 50°and poured into the container, where the target product is crystallized by cooling water from 50 to 18°C for 2 hours. Then DQC is filtered off and then the target product with a humidity of 55% is dried in an oven at a temperature of 50° to a residual moisture content of 8%.

The output of the DQC was 2.5% by weight of absolutely dry wood with a degree of purity of 96%.

The use of the proposed method will allow you to:

to increase the output of the DQC to 2.2-2.5% while maintaining high purity of the target product;

- to simplify the way, excluding technology complex and time-consuming preliminary abysmalia the Oia feedstock;

- to improve the environmental safety of the method, excluding from the process flammable, toxic solvents: ethyl acetate, n-hexane, benzene;

- to reduce the cost and improve the quality of the target product, since the latter is obtained in native form, with undisturbed natural structure, since the process is performed at low temperatures, in contrast to high-temperature counterparts, with the inevitable collapse patterns and losses of up to 70% of the final product.

The proposed method allows to obtain DQC with high yield and high purity, substantially simplify the process, reduce the time of the process and to allow the processing of large (hundreds of tons) crude oil.

1. The method of obtaining dihydroquercetin (DQC), including extraction of the last of the crushed wood of larch with an organic solvent under heating, distillation of the solvent, extraction of the target product from the aqueous portion of the extract, its crystallization from hot water and drying, characterized in that the extraction is carried out with an aqueous solution of ethyl alcohol containing organic part of 75-85% at a temperature of 45-50°C for 2-3 h at a ratio of crushed wood and extractant equal to 1:(7-10), obtained after distillation alcohol aqueous extract is cooled to 20-25°C for 20-30 min for deletion is of a resinous impurities, from deresinated extract is re-extracted with DQC methyl tertiary butyl ether at a ratio of 1:(0,3-0,45) for 2-3 h followed by the separation of the etheric portion of the extract and the process of evaporation of methyl tertiary butyl ether.

2. The method according to claim 1, characterized in that the wood of larch is used with a humidity of not more than 27%.

3. The method according to claim 1, characterized in that the extraction DQC methyl tertiary butyl ether is carried out at a temperature of 34-36°in the vacuum of 0.2 MPa.

4. The method according to claim 1, characterized in that the essential part of the extract containing dihydroquercetin, separated by settling in for 2-2,5 hours



 

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