Method of extraction of phenol and biphenols

FIELD: chemical industry; methods of extraction of phenol and biphenols from the homogeneous reactionary mixtures.

SUBSTANCE: the invention is pertaining to the method of extraction of phenol and biphenols from the homogeneous reactionary mixtures of the direct oxidation of benzene by hydrogen peroxide. The method includes delivery of the reactionary mixture containing benzene, water, phenol, the sulfolane and the reaction by-products (biphenols) in еру distillation plant consisting of two or more columns for production of one or more products basically consisting of the azeotropic mixture of benzene with water and phenol, and also the product consisting of sulfolane, phenol and the reaction by-products. The stream including sulfolane is mixed with the water solution of the base and benzene for formation of the salts of the phenols and the subsequent stratification of the mixture, extraction by benzene and separation in the flow column containing benzene and sulfolane, which is returned in the reactor. From the same column separate the stream including sodium phenolates in the water solution, which is treated with the sulfuric acid for extraction of the phenols from their salts. At the stage of the extraction separate the extracting solvent, after distillation of which in the tailings bottom product receive the biphenols water solution. The separated organic solvent recirculates in the system. The technical result of the invention is improvement of the process of separation of phenols and biphenols from the complex azeotropic mixtures containing sulfolane.

EFFECT: the invention ensures the improved process of separation of phenols and biphenols from the complex azeotropic mixtures containing sulfolane.

9 cl, 1 ex, 1 dwg, 1 tbl

 

The present invention relates to a process for recovering phenol and biphenolic by-products from solutions containing these products.

In particular, the present invention relates to a process for recovering phenol and biphenolic by-products from their homogeneous mixtures containing benzene, sulfolane and water.

Phenol is a useful product, which is used in the manufacture of synthetic resins, insecticides and antioxidants.

In industry the phenol is usually obtained by alkylation of benzene with propylene to form cumene, which are oxidized to the corresponding tertiary hydroperoxide, which, in turn, split into phenol and acetone in the presence of an acid catalyst.

After neutralization of the remaining acid, the reaction mixture is subjected to several successive distillations to separate the products and by-products from the unreacted reagents, which are then recycled into the reaction.

The recently proposed method of production of phenol by direct oxidation of benzene with hydrogen peroxide in the presence of silicalite titanium, which operates in the liquid phase in the presence of sulfolane as solvent (US 6133487).

The method, which allows to obtain the phenol from benzene oxidation with high yields, always accompanied by subsequent reactions that p is avodat education polyhydroxyalkane products (mainly befunolol) at concentrations depending on the reaction conditions.

Consequently, emerging from the reaction stream, in addition to resulting in the process of phenol, befunolol and resin contains a solvent sulfolane, unreacted benzene and water, the resulting reaction, and also introduced together with diluted hydrogen peroxide.

In this case, the use of traditional cleaning method, which includes the sequential Stripping of the various components, unprofitable, because after separation of the more volatile components (benzene, water and phenol), first it would be necessary to ward off sulfolan in order to remove by-products having a higher boiling point than the solvent sulfolane.

This solution is not only uneconomical, but also unsuitable for the Department of befunolol, such as catechol, which form with sulfolane azeotropic mixture with high boiling point.

In this case, it is impossible to even apply simple extraction of the aqueous solution of soda (US 5338453)as sulfolan infinitely miscible with water.

These disadvantages of the known methods, as it turns out, can be overcome by using the method proposed in the present invention, which is based on the use of the alkaline solution and benzene to separate befunolol from sulfolane after removal of the benzene, N2Oh and phenol contained the stream, coming out of the response.

The method in accordance with the present invention allows to extract biphenylene by-products dissolved in sulfolane; directly receive the purified solvent containing benzene, necessary for subsequent loading into the reactor for direct oxidation of benzene, and the solution befunolol in water and pure phenol.

In accordance with the foregoing objective of the present invention is a method for extracting phenol and befunolol from their homogeneous mixtures containing benzene, sulfolane and water, which comprises the following stages:

(a) feeding the reaction mixture containing benzene, water, phenol, sulfolane and the reaction by-products (biphenol), distillation unit consisting of two or more columns, for receiving the upper part of the column one or more products, mainly consisting of azeotropic mixtures of benzene with water and phenol, and in the lower part of the column - product consisting of sulfolane, the residual phenol and side reaction products;

(b) the filing of the azeotropic mixture of benzene with water in the condensation system consisting of one or more capacitors connected in series, in which after stratification share an aqueous phase and a benzene phase. The last part is sent back to the irrigation distillers, while water pasupuleti collect;

(C) feeding the product from the bottom of the column, coming from distillers stage (a), an aqueous solution of the base and benzene in one or more mixers and separators (D311) for the formation of salts from befunolol the purpose of the stratification system in the organic phase consisting of benzene, sulfolane, and the aqueous phase consisting of water, salts befunolol and parts of sulfolane;

(g) feeding the aqueous phase coming from the mixer/separator (D311), and benzene in column (C) extraction fluid liquid to obtain a water-saturated organic extract containing benzene and sulfolan, in the upper part of the column, and the purified product containing salts of phenols in aqueous solution, in the lower part of the column;

(d) feeding the organic phase obtained in stage (b) and (g), and water in system mixing/separation (D312) for organic stream containing sulfolane, benzene and water, and a saturated organic water flow, which is directed to the extraction column S;

(e) feeding the organic phase obtained in stage (d), in the distillation column S320, in which heterogeneous azeotropic mixture of benzene with water, with the maximum pressure, is separated in the upper part of the column and the product consisting of sulfolane, benzene and residual water is separated in the lower part of the column;

(g) the filing of the azeotropic mixture is, obtained in stage (e), in the condensation system consisting of one or more capacitors, in which the aqueous phase is separated completely removed and used to prepare an aqueous solution of the base, designed to obtain salts of phenols, and the benzene phase, which is sent back to irrigation columns;

(C) the supply of the pure product, out of the extraction column C, in the mixer and the acidification of its inorganic acid or CO2to extract phenols from their salts;

(I) the supply of water and salt solution obtained in stage (C), and extracting agent in the extraction column S to obtain an extract containing biphenol, in the upper part, and the pure product consisting of a water-salt solution containing the remains of the extracting agent, in the lower part;

(K) the supply of the pure product in a distillation column S to obtain residual extracting agent together with water in the upper part, and a water-salt solution, which is then sent for recycling or regeneration, in the lower part;

(l) feeding the extract coming from the column C, and the product leaving the top of column C, distillation column C, obtaining a heterogeneous azeotropic mixture extracting solvent with water in the upper part of the column and is of astora, containing water and biphenol, at the bottom of the drill string.

(m) the supply of the product emerging from the upper part of the column, condensing system, consisting of one or more capacitors, where they get the water phase, which is sent back to irrigation columns S on stage (l), together with an organic phase containing the extracting agent:

(h) feeding the organic phase leaving the condenser, distillation column C to obtain water-benzene mixture, which is recycled to stage (a), in the upper part of the column and extracting agent, which directly serves in the separating column C, in the lower part of the column.

In accordance with one embodiment of the present invention the method includes:

(a) feeding the reaction mixture containing benzene, water, phenol, sulfolane and side reaction products, in the first distillation column C to obtain a product consisting of azeotropic mixtures of benzene with water, in the upper part of the column, and the product includes residual benzene and water, sulfolan, phenol and the reaction by-products, in the lower part of the column;

(b) the filing of the azeotropic mixture of benzene with water in the condensation system consisting of one or more capacitors connected in series, in which after stratification share an aqueous phase and a benzene phase. Lastly the Yu partially sent back to the irrigation distillation column, while the aqueous phase is completely collected;

(C) submission of product exiting the bottom of column C, the second distillation column C220 to obtain a product containing benzene, water and traces of phenol and supplied again to the step (a), in the upper part of the column and a tail product comprising phenol, sulfolane and befunolol;

(g) feeding the tail of the product coming out of the distillation column C220, in a third distillation column S230, to obtain pure phenol in the form of a side of a shoulder strap, as well as to obtain in the upper part of the column distilled product containing light products (benzene and water), and the tail of a stream, consisting of sulfolane containing residues of phenol and befunolol, at the bottom of the drill string.

(d) feeding the tail of the stream exiting the column S230, an aqueous solution of the base and benzene in one or more mixers/separators (D311) for the formation of salts of phenols and benzene serves in such quantity to cause stratification of the system to the organic phase, consisting of sulfolane and benzene, and aqueous solution containing salts of phenol and a portion of the sulfolane;

(e) feeding the aqueous phase coming from the mixer/separator (D311), and benzene in column (C) extraction fluid liquid with the purpose of obtaining organic extract was saturated with water and containing benzene and sulfolan, the upper part of the column and the purified product, containing salts of phenols in aqueous solution, in the lower part;

(g) feeding the organic phase obtained in stage (d) and (e), and water (D312) mixing/separation to obtain an organic stream containing sulfolane, benzene and water, and a saturated organic water flow, which is directed to the extraction column S;

(C) feeding the organic phase obtained in stage (f), in a distillation column S320, in which heterogeneous azeotropic mixture of benzene with water, with maximum pressure, is separated in the upper part of the column and the product consisting of sulfolane, benzene and the remaining water is separated in the lower part of the column;

(and) feed azeotropic mixture obtained in stage (C), in the condensation system consisting of one or more capacitors, in which the aqueous phase is separated completely removed and then used to prepare an aqueous solution of the base, designed to obtain salts of phenols, and the benzene phase, which is then sent back to irrigation columns;

(K) the supply of the pure product, out of the extraction column C, in the mixer and the acidification of its inorganic acid or CO2to extract phenols from their salts;

(l) the supply of water and salt solution obtained in stage (K), and extracting agent to the extraction column S to obtain an extract, containing biphenol, in the upper part of the column, and the purified product consisting of a water-salt solution, in the lower part;

(m) the supply of the pure product in a distillation column Is to extract residual extracting agent together with water in the upper part of the column, and water-salt solution is sent for recycling or regeneration, in the lower part of the column;

(h) feeding the extract out of the extraction column C, and the product leaving the top of column C, distillation column S obtaining a heterogeneous azeotropic mixture extracting solvent with water in the upper part of the column and a solution containing water and biphenol, at the bottom of the drill string.

(a) submission of product emerging from the upper part of the column, condensing system, consisting of one or more capacitors, where they get the water phase, which is sent for irrigation columns S on stage (h), together with an organic phase containing the extracting agent;

(p) supply of part of the organic phase leaving the condenser, distillation column C to get in the upper part of the column of water-benzene mixture, which is then recycled to stage (a), and extracting agent, which directly serves in the separating column C, in the lower part of the column.

In accordance with one of the options is carried out the method according to the present invention, emerging from the reaction stream before it is fed into the distillation unit can be subjected to degassing in a single evaporator (D210) to remove most of the dissolved inert gases.

The evaporator operates at temperatures in the range from 20 to 100°and at a pressure of from 0.1 to 0.9 bar, preferably at temperatures in the range from 40 to 70°and a pressure of from 0.4 to 0.7 bar.

The stream exiting the evaporator, then fed to a distillation system.

Columns S, C220 and S230 are essentially in the same temperature conditions in the lower parts, i.e. at about 150-200°With, but at different pressures and temperatures in the upper parts.

In particular, column C operates at a pressure in the range from 0.1 to 0.9 bar and at a temperature of the upper part of the range from 20 to 100°column C220 operates at a pressure in the range from 0.5 to 0.1 bar and a temperature of the upper part of the range from 30 to 100°With, while column S230 operates at a pressure in the range from 0.01 to 0.1 bar and a temperature of the upper part of the range from 30 to 90°C.

Column S is designed for the separation of benzene and water in its upper part. Condensed product after stratification divided into water and the benzene phase. The last part is sent back to the column for irrigation, while the aqueous phase is completely collected.

Tail stream from the column contains the residual benzene and water, to avoid excessive temperature increase by the cube of the column.

Removing residual benzene and water contained in the tailings stream S perform in the second column (C220), which operates under a lower pressure than the previous column and the distillate from which also contains phenol, again served in S.

Tail the rest of the columns C220 guide to the next distillation column (S230), in which the sixth stage of pure phenol as a side product, while all possible present light products are concentrated in the distillate at the top of the column, and then re-directed to S.

Tail stream from S230, consisting of sulfolane containing residual phenol and biphenol, refer to the section of the Department of befunolol, in which it is first treated with excess aqueous base for the conversion of phenols present in the salt. Usually apply a solution of NaOH, KOH, Na2CO2To2CO3, Na3PO4To2PO4. Preferably used NaOH solution.

Then the stream is mixed with benzene in sufficient quantity for splitting the system in the aqueous phase containing alkali metal salts of phenols and part of sulfolane, and the organic phase consisting of sulfolane and benzene saturated with water.

After separation the aqueous phase is sent to to the column (S) SX, where it is treated with benzene for the extraction of the contained sulfolane, and thus extracted the product is saturated with water and consisting of benzene, sulfolane, and the purified product containing the reaction of alkali metals in aqueous solution.

Part of the extracting solvent is supplied from the upper part of the column C, the rest is a fresh portion of the benzene, the compensating part, consumed in the reaction.

The organic phase coming from D311 and S, first washed with water D312 to remove possible traces of salts dispersed in water, and then sent to distillation column (S320) for separating excess water. The surgery is performed by separating a heterogeneous azeotropic mixture of benzene with water, with the maximum pressure in the upper part of the column.

After separation of the condensate is separated into water and the benzene phase. The last fully sent back to the column for irrigation, while the aqueous phase is completely collected and used for preparation of the alkali solution used to obtain the salts of phenols.

Caudal flow column (S320) consists of sulfolane, benzene and water in concentrations suitable for returning the mixture in the reaction.

The purified product containing the reaction of sodium in the aqueous solution fed into the mixer together with the acid, suppose the equipment H 2SO4for the extraction of phenols from their salts. Thus obtained aqueous sulfate solution and extracting agent selected from aromatic hydrocarbons, alcohols, ketones, complex or simple esters, insoluble or partially soluble in water, in particular, cumene, benzene, tert-amyl alcohol, isopropyl ester, 3-pentanone, diisopropylate, butyl acetate, methyl isobutyl ketone, preferably methyl isobutyl ketone (MIK), served in the extraction column, while the extract containing biphenol in an organic solvent, and the purified product, consisting of sulfate in water saturated specified solvent.

The purified product, out of the extraction column, is fed into distillation column for steaming the remaining solvent, receiving at the tail of an aqueous solution of sulfate, which can be sent for recycling.

The flow of water coming from the upper part of the column Is also sent to S, for better steaming solvent. The column is also equipped with a reflux condenser, through which the condensed product is completely fed back into the column for irrigation.

Removing the extracting solvent is accomplished by the filing of an extract from S and vapors from the upper part of the column C, in the same distillation column (S), getting at the top (head) part of the heterogeneous and Europol mixture of the solvent with water, with maximum pressure.

After condensation of the distillate is separated into organic and aqueous phase. The last fully sent back to the column for irrigation, while the organic phase comprising an organic solvent saturated with water, again sent for extraction in S.

Finally, in the tail thread to receive an aqueous solution of befunolol.

As the organic solvent, warded off from S, contains a small amount of benzene, coming from a previous operation, a portion of the solvent (about 5%) should be subjected to distillation in the column S to remove benzene, avoiding, thus, its accumulation in the extraction cycle.

Thus, in the upper part of the column receives consisting of benzene and water distillate, which again served in S, while in the tail fraction receive an organic solvent, from which the benzene removed.

The method in accordance with the present invention is best understood by referring to the block diagram in the drawing, which shows a possible, but non-limiting embodiment of the invention.

Below is a working example illustrating, but not limiting the invention.

Example 1

For the extraction of phenol and befunolol follow the scheme shown in the drawing, based on:

the stream exiting the installation according to claim what izvodstvu phenol, consisting of 36 wt.%. benzene, 2 wt.% water, 4 wt.% phenol, 0.4 wt.% befunolol and 57.6 wt.% sulfolane;

- an aqueous solution of NaOH and benzene fed to the mixer/separator D311 in such quantity to obtain salts of phenols and cause the stratification system in the aqueous phase containing salts of phenols and part of sulfolane, and the organic phase consisting of sulfolane and benzene, respectively;

solution containing sulfuric acid at a concentration of 98 wt.%, fed to the mixer for separation of phenols from their salts.

The number and data related to individual flows are shown below in table 1.

12
Table 1
The stream exiting the reactorThe resulting phenolAn aqueous solution of NaOHH2SO4Water-salt solution for recyclingAqueous solutions of bifemales
No.ComponentsConsumption (kg/h)Weight %Consumption (kg/h)Weight %Consumption (kg/h)Weight%Consumption (kg/h)Weight %Consumption (kg/h)Weight% Consumption (kg/h)Weight %
1Benzene230480,03135,9276--87,1080,2449------
2H2About15834,9522,4684--32826,02092,304666,2452,000018043,60079,31989093,80771,0580
3Phenol25097,7793,911825000,000of 100.0000----0,9410,004193,8380,7332
4Catechol2150,0000,3351--------2150,00016,7999
5Hydroquinone1080,0000,1684--------1080,0008,4390
6Resin380,000 0,0592--------380,0002,9693
7Sulfolan366443,93857,1218--------0,0040,0000
8NaOH----2649,5857,4505------
9H2SO4------3245,98598,0000----
10Na2SO4--------4703,37120,6761--
11MICK----------0,0800,0006
About212,6020,0020----------
13N236,5390,0057----------
Consumption (kg/h)641512,84225000,00035562,7133312,23022747,91012797,729
PhaseLiquidLiquidLiquidLiquidLiquidLiquid
Temperature106,1179,4160,0050,00109,60105,43
(°)
Pressure (ATM)1,5000,00191,0001,0001,3501,150

1. The method of extraction of phenol and befunolol from their homogeneous mixtures containing benzene, sulfolane and water, which comprises the following stages:

(a) feeding the reaction mixture containing benzene, water, phenol, sulfolane and the reaction by-products (biphenol), distillation unit consisting of two or more columns, for receiving the upper part of the column one or more products essentially consisting of an azeotropic mixture of benzene with water and phenol, and in the lower part of the column - product consisting of sulfolane, phenol and side reaction products;

(b) the filing of the azeotropic mixture of benzene with water in the condensation system consisting of one or more capacitors connected in series, in which after stratification share an aqueous phase and a benzene phase, the latter partially sent back to the irrigation main line in the system, while the aqueous phase is completely collected;

(C) feeding the product from the bottom of the column of distillers stage (a), an aqueous solution of the base and benzene in the mixer/separator for the formation of salts of phenols and stratification system in the organic phase consisting of benzene, sulfolane, and the aqueous phase consisting of water, salts of phenols and parts of sulfolane;

(g) feeding the aqueous phase coming from the mixer/separator phases (D311), and benzene in column (C) extraction of the liquid fluid to be received in the upper part of the organic extract, which is rich in water and containing benzene and sulfolan, and in the lower part of the pure product containing salts of phenols in aqueous solution;

(d) feeding the organic phase obtained in stage (b) and (g), and water in system mixing/separation (D312) for receiving the upper part of the organic stream containing sulfolane, benzene and water, and a saturated organic water flow, which is directed to the extraction column S;

(e) feeding the organic phase obtained in stage (d), in the distillation column S320, in which heterogeneous azeotropic mixture of benzene with water, with maximum pressure, is separated in the upper part, and a product consisting of sulfolane, benzene and water is separated in the lower part;

(g) filing azeotrope is MESI, obtained in stage (e), in the condensation system consisting of one or more capacitors, in which the aqueous phase is separated completely removed and used to prepare an aqueous solution of the base, designed to obtain salts of phenols, and the benzene phase, which is then sent back to the column for irrigation;

(C) the supply of the pure product, out of the extraction column C, in the mixer and the acidification of its inorganic acid or CO2for the release of phenols from their salts;

(I) the supply of water and salt solution obtained in stage (C), and extracting agent in the extraction column S to obtain an extract containing biphenol, in the upper part and the pure product consisting of a water-salt solution, in the lower part;

(K) the supply of the pure product in a distillation column S to obtain residual extracting agent together with water in the upper part and the lower part of the water-salt solution, which is sent for recycling or regeneration;

(l) feeding the extract coming from the column C, and the product leaving the top of column C, distillation column S obtaining a heterogeneous azeotropic mixture extracting solvent with water in the upper part and of a solution containing water and Biff is Ola, in the lower part;

(m) submission of product coming out of the top, in the condensation system consisting of one or more capacitors, where they get the water phase, which is sent on irrigation columns S stage (l), and the organic phase containing the extracting agent;

(h) feeding the organic phase leaving the condenser, distillation column C to get in the upper part of the water-benzene mixture, which is then recycled to stage (a), and in the lower part - extracting agent, which directly serves in the separating column C.

2. The method according to claim 1, wherein distilling the installation at the stage of (a) consists of three columns S, C220 and S230, operating at temperatures in their lower parts from 150 to 200°With, but at different pressures and temperatures in the upper parts.

3. The method according to claim 2, in which the column S operates at a pressure of from 0.1 to 0.9 bar and a temperature of the upper part 20 to 100°C.

4. The method according to claim 2, in which the column C220 operates at a pressure of from 0.05 to 0.1 bar and a temperature of the upper part of from 30 to 100°C.

5. The method according to claim 2, in which the column S230 operates at a pressure of from 0.01 to 0.1 bar and a temperature of the upper part of from 30 to 90°C.

6. The method according to claim 1, in which the solution of the base in stage (C) are selected from NaOH, KOH, Na2CO3To2CO3, Na3PO4and K3RHO .

7. The method according to claim 1, wherein acidifying the environment at the stage (C) is an inorganic acid or CO2.

8. The method according to claim 1, in which the extracting agent at the stage (s) selected from aromatic hydrocarbons, alcohols, ketones, complex or simple esters, insoluble or partially soluble in water, in particular from cumene, benzene, tert-amyl alcohol, isopropyl ether, 3-pentanone, Diisopropylamine, butyl acetate, isobutyl ketone.

9. The method according to claim 8, in which the extracting agent is a mixture.



 

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11 cl, 1 dwg, 9 ex

FIELD: industrial organic synthesis.

SUBSTANCE: invention relates to production of phenol via acid catalytic decomposition of cumene hydroperoxide followed by isolation of phenol from decomposition products and purification of phenol to remove trace impurities including acetol. Purification of phenol is accomplished through hetero-azeotropic rectification with water. Acetol is isolated as a part of liquid-phase side stream from semiblind plate located within exhausting section of hetero-azeotropic rectification column. Side stream is supplemented by cumene and used to supply stripping column, from which fraction of acetol/cumene azeotropic mixture is taken as distillate and residue is returned under semiblind plate of hetero-azeotropic rectification column to be further exhausted. From the bottom of the latter, crude phenol is withdrawn and passed to final purification from the rest of reactive trace impurities. Acetol/cumene azeotropic mixture is subjected to heat treatment at 310-350°C, which may be performed in mixtures with high-boiling production waste or in mixtures with bottom product of rectification column for thermal degradation of high-boiling synthesis by-products, which bottom product is recycled via tubular furnace. Above-mentioned semiblind plate, from which side stream is tapped, is disposed in column zone, wherein content of water is minimal and below which contact devices are positioned with efficiency at least 7.5 theoretical plates. Side stream with cumene added to it is passed to the vat of stripping column with efficiency at least 15 theoretical plates.

EFFECT: minimized content of acetol in purified phenol and reduced power consumption.

5 cl, 3 dwg, 6 tbl, 4 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to new derivatives of glucopyranosyloxybenzylbenzene represented by the formula (I): wherein R1 represents hydrogen atom or hydroxy(lower)alkyl; R2 represents lower alkyl group, lower alkoxy-group and lower alkylthio-group being each group is substituted optionally with hydroxy- or (lower)alkoxy-group, or to its pharmaceutically acceptable salts. Also, invention relates to pharmaceutical composition eliciting hypoglycemic activity and to a method for treatment and prophylaxis of hyperglycemia-associated diseases, such as diabetes mellitus, obesity and others, and to their intermediate compounds. Invention provides preparing new derivatives of glucopyranosyloxybenzylbenzene that elicit the excellent inhibitory activity with respect to human SGLT2.

EFFECT: valuable medicinal properties of compounds.

13 cl, 2 tbl, 2 ex

The invention relates to petrochemistry and can be used in the production of phenol and acetone Kukolnik method

The invention relates to analytical chemistry of organic compounds and can be used for concentration of phenol in analytical control of natural water, drinking water and treated wastewater

The invention relates to a process for the production of phenol method Kukolnik

The invention relates to the field of production of phenol, as well as preparation of catalysts for this process

The invention relates to the synthesis of organic compounds, particularly to the technology of producing bisphenols, and can be used in the chemical industry for the production of monomers, antioxidants and biologically active substances
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