Process of producing isopropyl alcohol, process of producing phenol and isopropyl alcohol containing benzene hydrogenation products, and process of hydrogenating starting benzene-polluted acetone

FIELD: industrial organic synthesis.

SUBSTANCE: isopropyl alcohol production process comprises hydrogenation of starting acetone including from 0.01 to 10000 ppm benzene in presence of hydrogen and catalyst to give isopropyl alcohol and benzene hydrogenation products, acetone and benzene contained in feedstock being hydrogenated simultaneously. In its second embodiment, isopropyl alcohol production process comprises product separation stage. Process of producing phenol and isopropyl alcohol containing benzene hydrogenation products comprises stages: alkylation of benzene with isopropyl alcohol and/or propylene to form cumene, oxidation of resulting cumene into cumene hydroperoxide, acid cleavage of cumene hydroperoxide to produce phenol and acetone including from 0.01 to 10000 ppm benzene, preferably concentration of produced benzene-polluted acetone, and catalytic hydrogenation of benzene-polluted acetone into isopropyl alcohol containing benzene hydrogenation products, hydrogenation of benzene and acetone proceeding simultaneously.

EFFECT: enhanced process efficiency.

3 cl, 1 dwg, 1 tbl

 

The present invention relates to a process for the hydrogenation of initial acetone containing benzene, obtaining isopropanol.

Isopropanol is a widely used intermediate compound in organic synthesis, as well as an important commercial solvent.

Acetone is available in large quantities as a by-product in the manufacture of phenol by Komolova method. In Komolova the way the alkylate benzene with propene and/or isopropanol and get cumene, cumene oxidized to cumene hydroperoxide, and cumene hydroperoxide were cleaved with acid to obtain phenol and acetone. The acetone obtained at the specified Komolova method, contaminated with benzene. As indicated, for example, in European application EP-A-0434485, production of acetone in Komolova the way is a disadvantage, because the demand for phenol is growing much faster than the demand for acetone. Therefore, in application EP-A-0434485 invited to gidrirovanii acetone obtained by Komolova the way in isopropanol and return isopropanol in comology process.

In the application EP-A-0434485 not specified that in acetone, which receive Komolova way, benzene is present.

If the acetone obtained by Komolova method described in the application EP-A-0434485 really contains benzene, the benzene is returned to the process stream obtained is isopropanol does not affect the process itself. Any amount of benzene that is present in recyclorama thread may be reused upon receipt of cumene. Thus, in the process described in the application EP-A-0434485, it is advantageous to gidrirovanii only the acetone.

Moreover, if acetone does contain benzene, the specialist is entitled to expect that the response will come only acetone. Hydrogenation of benzene is much harder than the hydrogenation of acetone. This illustrates, for example, the article by E. de Ruiter and J.C.Jungers, Bull. Soc. Chim. Belg., 58, p.230, 1949, which States that in the case when hydronaut mixture of acetone and benzene, acetone reacts first.

In recent times it has become desirable to turn the acetone obtained by Komolova the way in isopropanol, which can be used for other purposes in addition to recycling in comology processeddata the presence of any quantity of benzene makes uncomfortable using isopropanol for other purposes, in addition to returning in comology process.

Remove traces of benzene from acetone by distillation is very difficult. Removal of benzene from isopropanol after hydrogenation is even more difficult because the boiling point of benzene and isopropanol close.

The present invention therefore is a method in which acetone contaminated with benzene, such as acetone, obtained by ku olowalu method, can be profitably converted into isopropanol, which can be used for other purposes, in addition to recycling.

This cost-effective process has been found by hydrogenation of the available benzene.

In accordance with the invention features a method of producing isopropanol, in which the original contaminated with benzene, acetone, containing from 0.01 to 10000 ppm of benzene, hydronaut getting isopropanol and products of hydrogenation of benzene and in which the hydrogenation of acetone and benzene are at the same time.

The method according to the present invention has the advantage that it can be used to obtain isopropanol containing a reduced amount of benzene or practically do not contain benzene, which can find various applications.

Under isopropanol, which practically does not contain benzene, understand isopropanol, which contains less than 2 ppm (2 mg/kg), acceptable less than 1 ppm (1 mg/kg), preferably less than 0.4 ppm (0.4 mg/kg), more preferably less than 0.1 ppm (0,1×10-6), even more preferably less than 20 parts per billion (20 mg/kg), and most preferably does not contain benzene.

In the process of the present invention, the benzene may, for example, gidrirovaniya in cyclohexane, cyclohexene or cyclohexadiene.

The hydrogenation is preferably under argueta more than 70% of benzene, more preferably over 90%, even more preferably more than 95% and most preferably from 99% to 100% benzene.

Preferred factors that affect the hydrogenation of benzene, are the type and amount of catalyst, temperature, quantity of each of the reagents or the feed rate with which each reactant fed into the reactor. Hydrogenation of benzene is predominantly carried out using a catalyst of a particular type, capable of gidrirovanii benzene, while all other factors are preferably chosen in such a way as to make the optimal hydrogenation process.

Hydrogenation of acetone and benzene in the original acetone, benzene polluted, can be implemented in one or more separate stages, but mainly their hydrogenation carried out at the same time. Thus, the catalyst is mainly a catalyst capable of simultaneously gidrirovanii acetone and benzene.

Hydrogenation of acetone and benzene mainly carried out in the presence of a catalyst containing a metal, which is capable of hydrogenation.

Preferred metals for the hydrogenation include copper, Nickel, platinum, palladium, ruthenium and rhodium. Can be used only one metal or combination of metals.

The metal is mainly applied to novtel is. Suitable carriers are carbon, aluminum oxide, silicon oxide, zirconium oxide and titanium oxide. A preferred carrier is silica, as the use of media silicon oxide leads to a very high selectivity in respect to the hydrogenation of acetone to isopropanol. Preferred examples of native silicon oxide are diatomaceous earth, precipitated silica and silica gel.

A particularly preferred catalyst is a hydrogenation catalyst containing Nickel, mainly supported on a carrier. Most preferred is a catalyst containing Nickel on a carrier of silica.

For practical reasons, at the present time can be used catalysts containing media from 5% wt./mass. up to 80% wt./mass. metal. If metal for hydrogenation is Nickel, the preferred are catalysts containing more than 25% of the mass./mass. Nickel, mostly more than 50% of the mass./mass. Nickel and more preferably in the range from 50 to 70 wt. -%/mass. Nickel inclusive.

The preferred method of providing simultaneous hydrogenation of acetone and benzene is the use of a Nickel catalyst, the dispersion and the Nickel content which is such that the surface area of the Nickel is at least 5 m 2Nickel per gram of catalyst. More preferably the surface area of the Nickel is at least 20 m2Nickel per gram of catalyst and most preferably the surface area of the Nickel is at least 30 m2Nickel per gram of catalyst. Suitable practical upper limit is obtained from the value of 50 m2Nickel per gram of catalyst.

The surface area of the Nickel can be determined by measuring the capacitance of the monolayer to chemisorption hydrogen, as described in J.W.E.Coenen and B.C.Linsen, "Physical and Chemical Aspects of Adsorbents and Catalysts", B.C.Linsen, ed. Academic Press (1970) 471 or R.Z.C. van Meerten, A.H.G.M.Beaumont, P.F.M.T. van Nisselrooij and J.W.E.Coenen, Surface Sci 135 (1983) 565. When measuring the surface area of Nickel monolayer is defined as the amount of hydrogen absorbed in the hydrogen pressure of 1 bar and a temperature of 293 K. the Amount of adsorbed hydrogen is determined after grinding at a temperature of 725 To within 4 hours, subsequent vacuum for 2 hours at a temperature of 675 To and controlled puffing.

The catalyst preferably has a bulk density in the range of 800-1200 kg/m3, preferably has a BET surface area in the range of 100-250 m2/g, preferably has a pore volume in the range from 0.20 to 0.50 cm3/g and preferably has a diameter of extrudate in the range from 1 to 6 mm

Produce the R is mainly in the form of a fixed layer. In the most preferred embodiment of the invention the method according to the present invention is carried out in the feed mode a small flow of reagents. I.e. liquid acetone served in a thin stream along the surface of the catalyst, which is placed in an atmosphere filled with gaseous hydrogen.

The molar ratio of hydrogen to acetone is preferably at least 1. More preferably the value of the molar ratio of hydrogen to acetone is in the range from 1:1 to 10:1, most preferably in the range from 1.5:1 to 5:1.

The hydrogenation process can be carried out in a wide range of temperatures, pressures in the reactor and used velocities of liquid and gas along the surface. Depending on the type of catalyst, each of these reaction conditions to optimize in such a way as to obtain optimum hydrogenation of benzene. For example, a less active catalyst requires a higher reaction temperature. Further, the use of higher velocities of liquid and gas along the surface will require higher temperatures, while the use of lower reaction temperatures may require the use of a lower velocities of liquid and gas along the surface. The preferred temperature in the reactor is in the Arvale from the 40° With up to 150°S, more preferably in the range from 60°to 130°C. the aging of the catalyst may require a higher temperature. The pressure of the reaction is preferably in the range from 1 to 100 bar, more preferably in the range from 10 to 40 bar. Higher pressure leads to an increase in the cost of gas compression, while a lower pressure can lead to a low rate of conversion.

The speed of movement of gas along the surface is preferably in the range of 0.01-10 m/s and the velocity of a fluid along the surface is preferably in the range of 0.0001-0.1 m/s

The gas is primarily essentially pure hydrogen, while the hydrogen may contain a small amount, for example, in the range from 0 to 15% wt./mass., in particular, methane, ethane, nitrogen and other impurities.

The method according to the present invention has the advantage that it can be carried out for the source of acetone containing benzene in a wide range of concentrations. The possible content of benzene in the original acetone may be in the range from 0.01 ppm to 10000 ppm, more preferably from 0.1 ppm to 100 ppm the Method according to the present invention further provides special advantages for the source of acetone containing at least 0.5 ppm benzene, and these advantages the society become even more pronounced, when the concentration of benzene increases at least up to 1 ppm Advantages are even more pronounced for the source of acetone containing at least 1.5 ppm benzene.

The method according to the present invention is very convenient to combine process of production of phenol. Thus, the present invention features a process for the production of phenol, including:

a) alkylation of benzene with isopropanol and/or propylene with obtaining cumene;

b) oxidation of cumene with stage a) cumene hydroperoxide;

c) the acid cleavage of cumene hydroperoxide to obtain phenol and acetone contaminated with benzene;

d) preferably the concentration of acetone contaminated with benzene, which is obtained in stage C);

e) hydrogenation of acetone contaminated with benzene, which is obtained in stage d), in isopropanol containing products of the hydrogenation of benzene.

Stages (a) through (C) is conveniently carried out, as described, for example, in application EP-A-0371738 and EP-A-0434485. Stage d) it is convenient to carry out the distillation. Stage (e) is conveniently carried out, as described previously in the present description. Isopropanol obtained in stage e), can be used as a solvent in various applications. If necessary, isopropanol, obtained in stage e), you can return to the step a). Such recycling is convenient to carry out, as described in applications EP-A-0371738 THE EP-A-0434485.

To further improve the quality of isopropanol, the method according to the present invention is preferably combined with a number of separation stages.

Thus, the invention also proposes a method of hydrogenation of the initial acetone contaminated with benzene, as described previously, which includes the following stages:

i) the simultaneous hydrogenation of both components of the initial acetone containing from 0.01 ppm to 10000 ppm of benzene, in the presence of hydrogen, with the formation of the reaction product containing isopropanol and products of hydrogenation of benzene;

ii) separating the gaseous products from the reaction product obtained in stage i), and the separation of liquid reaction product;

iii) the separation of light by-products and unreacted acetone from the liquid reaction product obtained in stage (ii), and the allocation of the resulting crude isopropanol;

(iv) separation of heavy by-products from the crude isopropanol obtained at stage iii), and removing the product in the form of purified isopropanol;

v) recycling unreacted acetone and/or part of the lung by-products obtained in stage (iii), and/or part of the heavy by-products obtained in stage iv), on stage hydrogenation of i).

This process includes a number of stages of separation of substances that results in isopropanol activecache quality. Moreover, recycling of by-products, as indicated at stage (v), improves the selectivity of the process.

The method may be performed periodically, paliperidone and continuous process. The process is conveniently carried out as continuous. In the specified continuous process pre-heated and preferably a pre-prepared mixture of the original acetone contaminated with benzene, and hydrogen serves on stage (i), thereby starting the process. Then acetone and benzene, mostly at the same time, hydronaut. The product stream from step (i) may contain isopropanol, by-products, such as diisopropyl ether and/or hexyleneglycol, not necessarily the products of hydrogenation of benzene, such as, for example, cyclohexane, and, if they are present, unreacted hydrogen and/or acetone.

In phase ii) next, perform a separation of the gaseous products from the reaction product obtained in stage i). This is mainly used gas-liquid separator. Gaseous products, in addition to other volatile by-products may contain unreacted hydrogen. Part of the gaseous product preferably otdovat, and the remaining amount is preferably recyclery at stage i). In phase ii) are the liquid product of the reaction. Then at stage iii) light by-products and narora Ravasi acetone is separated from the specified liquid reaction product. The specified separation is mainly carried out by distillation. After this division receive the product in the form of crude isopropanol from which to stage iv) separating the heavy by-products. The specified separation is also preferably carried out by distillation. After the division receives the product in the form of purified isopropanol. In the preferred embodiment, this invention purified isopropanol is subjected to further processing and receive the final product in the form of isopropanol. Specified additional processing in order to obtain the final product in the form of isopropanol mainly carry out the following additional stages:

vi) the allocation of the azeotropic mixture of isopropanol, water and cyclohexane purified from isopropanol obtained at stage iv), and the final product in the form of isopropanol;

vii) the separation of the azeotropic mixture of isopropanol, water and cyclohexane obtained in stage vi, the water and the azeotropic mixture of isopropanol and cyclohexane; and

viii) an optional recycling of the azeotropic mixture of isopropanol and cyclohexane obtained in stage vii), at stage vi).

The separation of the phase vi and phase vii) is mainly carried out by distillation.

Unreacted acetone and part of the lung by-products obtained in stage (iii), and part of thee is elih products with stage iv) return to hydrogenation in stage (i). In a preferred embodiment of the invention the flow of products, recyclorama with stage iii) stage i), mainly contains acetone and diisopropyl ether. The flow of products, recyclorama with stage iv) at stage i), preferably mainly contains hexyleneglycol. By recycling these products, the selectivity is improved, resulting in higher yield of isopropanol.

Illustration of the method according to the present invention is then carried out with reference to the drawing.

A stream of acetone (101), contaminated with benzene, mixed with a flow of fresh hydrogen (103), is preheated in the heat exchanger (105), and fed into the reactor (107)containing 55-62% wt./mass. catalyst of Nickel on silica, the surface area of the Nickel which is 34 m2/g, in the form of a fixed catalyst layer. Stemming the flow of reaction product (109) is removed from the reactor (107) and is cooled in the heat exchanger (111). After cooling the gaseous compounds from the product stream is separated from the liquid compounds in a gas-liquid separator (113). From the top of the gas-liquid separator (113) shows the gas flow (115). Part of this flow (115) otdovat (117), while the rest of recyclery in the reactor (119). From the bottom of the gas-liquid separator to remove the liquid stream (121) and submit it to disti the air column (123). From the top of the distillation column (123) allocate the flow of light products (125). Stream (125) consists mainly of unreacted acetone and a by-product in the form of diisopropyl ether. Some of the listed stream of light products (125) otdovat (127), while another part recyclery in the reactor (129). From the bottom of distillation columns specified (123) remove the flow of crude isopropanol (131) and send it to the second distillation column (133). From the lower part of this second distillation column (133) remove the flow of heavy products (135). Stream (135) mainly contains a by-product in the form of hexyleneglycol. Part of this flow of heavy products (135) otdovat (137), while the rest of recyclery in the reactor (139). From the upper part of this second distillation column (133) remove the flow of purified isopropanol (141) and send it to a third distillation column (143). From the bottom of the third distillation column (143) receive the flow of the final product - isopropanol (145). From the top of the third distillation column (143) receive flow azeotropic mixture of cyclohexane, water and isopropanol (147), served in the fourth distillation column (149). From the bottom of the fourth distillation column (149) remove the water flow (151)cast. From the top cha the minute of the fourth distillation column (149) allocate stream azeotropic mixture of cyclohexane and isopropanol (153), which recyclery in a third distillation column (143).

The invention is further illustrated by the following examples.

Examples

In the reactor in the form of a tube with a length of 35 cm and an inner diameter of 10 mm to form a fixed layer containing 5 g of the catalyst, as indicated in table 1. The original acetone containing 50 ppm (50 mg/kg) benzene, placed in the reactor in a quantity, expressed in parts by weight on the spatial volume per hour (WHSV), as shown in table 1. The original acetone hydronaut in the presence of hydrogen and catalyst at the temperature and pressure shown in table 1. The degree of conversion of benzene and acetone are shown in table 1. Selectivity for ISO-propanol, calculated with respect to all products of the conversion of acetone exceeds 99%. The content of benzene in the stream of the obtained product in the form of isopropanol determined by gas chromatography/mass spectrometry mass 78 in odnoionnoi mode. Benzene content in the resulting isopropanol are listed in table 1.

Table 1
ExampleCatalystT°)P (bar)mol H2/say

acetone
WHSV (kg of raw material/kg of catalyst/hourThe conversion of acetone (% wt./mass.) Conversion of benzene (% wt./mass.)The number of benzene remaining in the product
1Leuna 6564 tl 1.2902021,5>to 99.9>to 99.9<20 ppb
2Leuna AS 65121302021,599,9>to 99.9<20 ppb
3Leuna AS 6512702020,5>to 99.9>to 99.926 parts per billion
4Leuna AS 6512902020,5>to 99.9>to 99.9<20 ppb
5Leuna AS 65121102020,5>to 99.9>to 99.9<20 ppb

- Leuna AS 6512 denotes the catalyst 55-62% wt./mass. Nickel on silica, the surface area of the Nickel which is 34 m2/g of catalyst bulk density is 850-1150 kg/m3, BET-surface area is 180-240 m2/g catalyst and a pore volume of 0.25-0.45 cm3/g of catalyst (catalyst Leua 6512 AS receive CRI KataLeuna).

- Leuna 6564 1.2 tl denotes the catalyst 28% wt./mass. Nickel on alumina, the surface area of the Nickel which is 43 m2/g of catalyst bulk density is 810-910 kg/m3, BET-surface is 100-120 m2/g of catalyst and the pore volume is 0,38-0,46 cm3/g of catalyst (catalyst Leuna 6564 tl 1.2 receive from the company CRI KataLeuna).

1. The method of producing isopropanol, in which the original acetone containing from 0.01 to 10000 ppm of benzene, hydronaut in the presence of hydrogen and catalyst to obtain isopropanol and hydrogenation products of benzene, in which the hydrogenation of acetone and benzene in the feedstock flows simultaneously.

2. The method according to claim 1, wherein the hydrogenation is carried out in the presence of a catalyst containing Nickel.

3. The method according to claim 2, in which the hydrogenation is carried out in the presence of Nickel catalyst, the surface area of the Nickel which is at least 15 m2Nickel per gram of catalyst.

4. The method according to claim 2 or 3, in which the catalyst is mainly in the form of a fixed layer.

5. The method according to claim 1 or 2, in which the process is carried out at a flow small flow of the reactants.

6. The method according to claim 1 or 2, in which the acetone contains from 0.1 to 100 ppm benzene.

7. Method for production of phenol and isopropanol containing products guide is investing benzene, including:

a) alkylation of benzene with isopropanol and/or propylene to form cumene;

b) oxidation of cumene obtained in stage a), cumene hydroperoxide;

c) the acid cleavage of cumene hydroperoxide to obtain phenol and acetone contaminated with benzene containing from 0.01 to 10000 ppm benzene;

d) preferably, the concentration of acetone contaminated with benzene, which is obtained in stage C);

e) hydrogenation contaminated with benzene acetone, obtained in stage d) and containing from 0.01 to 10,000 ppm, in the presence of hydrogen and catalyst in isopropanol containing products of hydrogenation of benzene, and hydrogenation of acetone and benzene are at the same time.

8. The method according to claim 7, in which stage e) is carried out in the presence of a catalyst containing Nickel.

9. The method of hydrogenation of the initial acetone contaminated with benzene, comprising the following stages:

(i) hydrogenation of the initial acetone containing from 0.01 to 10000 ppm of benzene, in the presence of hydrogen and catalyst, and the hydrogenation of acetone and benzene in the feedstock proceeds simultaneously with the formation of the reaction product containing isopropanol and products of hydrogenation of benzene;

ii) separating the gaseous products from the reaction product obtained in stage i), the allocation of ginkgophyta reaction;

iii) the separation of light by-products and unreacted acetone from the liquid reaction product obtained in stage (ii), and the allocation of the resulting crude isopropanol;

(iv) separation of heavy by-products from the crude isopropanol obtained at stage iii), and the allocation of product in the form of purified isopropanol;

v) recycling unreacted acetone and/or part of the lung by-products obtained in stage (iii), and/or part of the heavy by-products obtained in stage iv), on stage hydrogenation of i).



 

Same patents:

FIELD: petrochemical processes.

SUBSTANCE: hydrocarbon feedstock containing at least 1 vol % of at least one 5- or 6-membered cyclic hydrocarbon is subjected to preliminary processing, which consists in that feedstock is brought into contact with catalyst in presence of hydrogen under conditions favorable for selective opening of the cycle of cyclic hydrocarbon followed by isomerization stage wherein preliminarily processed feedstock comes into contact with isomerization catalyst to produce triptane-containing product stream.

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34 cl

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11 cl, 2 dwg, 1 tbl, 1 ex

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FIELD: chemical industry; methods of production of phenol and acetone.

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EFFECT: the invention ensures reduction of formation of hydroxyacetone, which one worsens the quality of the commercial phenol.

5 cl, 4 ex, 8 tbl

FIELD: organic chemistry, chemical technology.

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12 cl, 5 ex

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11 cl, 1 dwg, 9 ex

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5 cl, 3 dwg, 6 tbl, 4 ex

FIELD: organic chemistry, medicine, pharmacy.

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13 cl, 2 tbl, 2 ex

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EFFECT: the invention ensures reduction of formation of hydroxyacetone, which one worsens the quality of the commercial phenol.

5 cl, 4 ex, 8 tbl

FIELD: organic chemistry, chemical technology.

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8 cl

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to technology for producing phenol and acetone by cumene method, in particular, to a stage for separating cleavage products of alkylaryl hydroperoxide. Method involves separating a mixture of cleavage products for at least three fractions in a single distillation step by charging the mixture of cleavage products into lateral section of fractionating column, removal the first ketone-containing fraction through the upper part of fractionating column, removal of the second fraction containing substituted or unsubstituted phenol through the bottom part of column, and removal of the third fraction containing unreacted mono-, di- and/or trialkyl-substituted benzene and hydroxyketone as a side flow. The side outlet channel of the flow is located above the site for charging the mixture of cleavage products in fractionating column. The first fraction contains at least 75 wt.-% of ketone containing in the cleavage product before carrying out the distillation stage. Invention provides improvement of economy indices of the process due to reducing material and energetic consumptions and enhancing purity degree of final products.

EFFECT: improved method for treatment.

21 cl, 2 dwg

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to manufacturing phenol by cumene method, in particular, to a step for treatment of final product and preparing phenol of high purity degree. Method for treatment of crude phenol is carried out for two steps. At the first step method involves oxidation of acetol, aldehydes and α-methylstyrene with air oxygen in phenol medium by using a heterogeneous catalyst comprising metals with transient valence. At the second step method involves condensation of oxidation products and non-oxidized products by using a heterogeneous acid catalyst. Separation of compounds in the process of phenol treatment is carried out on the final step of isolation of the commercial product by distillation method. At the first stage metal compounds of by-side subgroups 1 and 6 and metals of 8 group of Periodic system on neutral or acid carrier are used as a catalyst preferably. At the second step alumosilicate contacts based on zeolites of type "X" or "Y", or other zeolites comprising or not comprising promoting and modifying additives are used as a catalyst. Invention provides the high degree of purification of phenol from impurities and the improvement of economy indices of the process.

EFFECT: improved method for phenol treatment.

12 cl, 5 ex

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