Method of production of phenol and acetone

FIELD: chemistry.

SUBSTANCE: method includes two-stage acid-catalysed decompounding of cumene hydroperoxide in series reactors under heat resulted in simultaneous generation dicumene peroxide in the first stage followed with its decompounding in reaction medium environment in the second stage. Thus any catalytic agent is not used; it is prepared in separate reactor immediately prior to introduce to the first reactor of cumene hydroperoxide decompounding by mixing sulphuric acid with phenol in ratio 2:1 to 1:1000 and keeping produced mixture at temperature 20-80°C within 1-600 minutes.

EFFECT: method allows for considerable yield reduction of hydroxyacetone.

4 cl, 7 tbl, 6 ex

 

The present invention relates to the field of industrial organic synthesis, more precisely, to obtain phenol and acetone Kukolnik way.

The known method for production of phenol and acetone by oxidation of cumene with oxygen with subsequent acid-catalyzed decomposition of cumene hydroperoxide allows to obtain both the desired product in high yield (Kruglov D., Golovenko BN. Joint production of phenol and acetone. M, Goskomizdat, 1964). It is widely used to manufacture these products as the major in the world.

Known methods for producing phenol and acetone in which to reduce the output of phenolic resin products of the oxidation of cumene containing cumene hydroperoxide (CHP), cumene, dimethylphenylcarbinol (DMPC), split in two stages in the presence of sulfuric acid. In the first stage at a temperature of 55-80°To carry out the decomposition of the majority (97-99%) of the CCP and synthesis of dicumylperoxide (DCT) of DMPC and the CCP, and the second at a temperature of 80-120°With, in the resulting reaction mixture containing phenol, acetone, dimethylphenylcarbinol (DMPC) and dicumylperoxide (DCT), add acetone in an amount of 1.5-1.8 times its initial concentration. When this occurs, the splitting of the DCT formed in the first stage, decomposition of the remaining CCP and dehydration remaining DMFC (Russian p the tents No. 2068404, No. 2121477).

These methods allow to reduce significantly the quantity of generated by-products in comparison with one-stage decomposition (exit resin 25 kg/t of phenol), at the same time, the resultant byproduct of hydroxyacetone remains at a high level (and sometimes increased).

Hydroxyacetone is a source of formation of 2-methylbenzofuran that it is difficult to separate from phenol and which impairs the color index commodity phenol. Remove hydroxyacetone of phenol with an alkaline processing complicates the process (Vasiliev I.I., Zakashansky V.M. Sat. "The processes of oil refining and petrochemistry ", SPb, Giord, 2005, S. 344).

Reduction of hydroxyacetone decomposition of the CCP for phenol and acetone reach by conducting the reaction in an excess of phenol (RF patent No. 2291852 and U.S. patent 7109385). However, these methods require to return a portion of the commodity product of phenol, which has already passed all the stages of selection, on the stage of decomposition of the CCP, which will certainly lead to performance degradation of the installation due to the increased load on the system for isolation and purification of phenol.

Closest to the proposed method of decomposition of the CCP is a method of decomposition, implemented in two stages (Russian patent No. 2142932 - prototype).

The process is carried out in three successive installations is the R reactors mixing in the first stage and in the reactor displacement in the second stage. In the first stage decomposition of the CCP carried out in conditions that are close to isothermal at a temperature of 47-50°C, concentration of catalyst is sulfuric acid, equal 0,018 at 0.020 wt.% and additional dilution of the reaction mixture with acetone in an amount equal to 5-8 wt.% regarding the amount of the CCP. When this reacts almost all of the CCP, as part of the CCP and DMFC formed DCT.

In the second stage, the process is carried with partial neutralization of sulfuric acid with ammonia with the formation of hydrosulphate of ammonia at a temperature 120-146°and with the addition of a quantity of water. The concentration of sulfuric acid 0,09-0,10 wt.%. The decomposition of the CCP and CSD occurs in a reaction medium containing phenol and acetone formed from HPC and advanced input acetone.

The disadvantages of the prototype method are a significant number of hydroxyacetone in the resulting phenol, which according to the statement of the authors of the process is 1300 ppm in the reaction mass decomposition of the CCP (the author's report of the prototype method at the conference "prospects of development of chemical processing of fossil fuels" HPGE-2006, 12-15 September 2006, Saint-Petersburg; "Hemostat", St. Petersburg, 2006, s), which significantly reduces its quality and the need for partial neutralization of sulfuric acid with ammonia, which complicates the technology and process control.

To reduce the output g is toxicity decomposition of CPC decomposition technical GPC is carried out in the presence of a catalyst, prepared in a separate reactor immediately prior to its entry into the reactor for the decomposition of the CCP by mixing phenol with sulfuric acid at a temperature of from 20 to 80°and the ratio of sulfuric acid: phenol from 2:1 to 1:1000 and maintaining this mixture at this temperature for 1-600 minutes. The concentration of sulfuric acid in the environment of the reaction products is 0,002-of 0.015 wt.%. Used in the proposed process, the sulfuric acid has a concentration of not less than 75%, it is possible to use oleum.

The process is carried out in two stages in at least two serially connected reactors. At the first stage in the first reactor by circulation of the reaction mass carry out the decomposition of technical CCP at a temperature of 40-75°in the presence of the above catalyst. The concentration of the catalyst depends on the reactor temperature, the ratio of phenol:acetone, water content and DMPC in raw materials. The feed rate should not exceed 10% of the speed of circulation of the reaction mass (preferably less than 5%), the ratio of circulation (the ratio of the flow rate of the circulating mass flow rate of supply of raw materials - technical CCP) with more than 9. In these conditions, the conversion of CCP, equal 95-99,8%, is decomposed with the formation of phenol and acetone, as well as the synthesis of the DCT of the CCP and DMFC.

In the second stage in the latter auctore at a temperature of 90-140° To carry out the decomposition of the synthesized DCT and the rest of the CCP. Unlike the prototype method there is no need partial neutralization of the catalyst, as in the first stage of the process uses a much smaller concentration. This allows to simplify the equipment used for the decomposition of the CCP.

To regulate the process of decomposition of the DCT may require the introduction into the reaction mass addition of water in an amount up to 1% of the reaction mass. The amount of this water depends on the content DMPC in the technical code of civil procedure, because it depends on the number of escaping the reaction of water due to dehydration DMFC. Increasing the water content in the reaction mass reduces the rate of decomposition of the CCP and CSD, as well as the rate of formation of by-products - cumylphenol and dimers AMC. The feed rate of water to regulate in such a way as to maximize the selectivity of the process of formation of phenol and acetone.

Dilution of the reaction mixture during the acid-catalyzed decomposition of the CCP, for example, acetone reduces the yield of the condensation products AMS - dimers and cumylphenol.

In the above process conditions using technical GPK similar composition of output hydroxyacetone reduced to 1.5-2 times that can improve the quality of commercial pheno is and when applying the same treatment system. In addition, the reduction of use of sulfuric acid leads to the reduction of consumption of alkali used to neutralize the acid, which ultimately reduces the amount of mineral waste products, in particular sodium sulfate.

To maintain in the reactor set temperature generated by decomposition of the CCP dissipate heat by means of heat exchangers, preferably built into the reactors.

A distinctive feature of the proposed method is the use of a catalyst prepared in a separate reactor a mixture of sulfuric acid and phenol in a ratio of from 2:1 to 1:1000 and kept at a temperature of 20-80°for 1-600 minutes.

Industrial applicability the present invention is illustrated by the following examples.

Example 1.

The decomposition of cumene hydroperoxide is conducted on a pilot plant consisting of two reactors: reactor decomposition of the CCP first stage with a volume of 12 ml, equipped with a circulating loop, and the second stage reactor with a volume of 7 ml, representing a reactor displacement. The reaction mass from the first stage reactor partially served on the second reactor, and partially returned to the inlet of the first reactor, thus conducting its circulation. In the flow of the reaction mass at the entrance to the first stage reactor serves a catalyst and raw materials the composition shown in table 1. When carrying out the reaction using the raw material of another composition, the results will differ from those shown in the examples of this invention, however, the positive effect of its use will continue. The catalyst is prepared by mixing concentrated sulfuric acid with phenol, which serves two pumps in a temperature-controlled reactor with a capacity of 10 µl from which the mixture enters the reactor for the decomposition of the CCP.

Table 1
Raw materials used for the decomposition of CPC
ComponentContent, wt.%
1Gasoperated cumene (CCP)82.30 level
2The cumene10,32
3Dimethylphenylcarbinol (DMPC)5,27
4The acetophenone1,03
5Water0,2
6Dicumylperoxide (DCT)0,30
7Phenol0,02
8Unidentified0,56

In the reactor for the decomposition of the CCP serves raw materials indicated in table 1 the composition and the catalyst that p is to obtain continuously a mixture of concentrated sulfuric acid, supplied with a speed of 1 mm/h, and phenol, served with a speed of 9 μl/h (ratio 1:5), and keeping them in the mixture for 60 minutes at a temperature of 50°S. this flow corresponds to the concentration of sulfuric acid in the reaction medium 0.007 wt.%. The speed of circulation of the reaction mass is 500 ml/hour, the Temperature in the reactor is maintained at 40°With through coolant supply proper temperature in the jacket of the reactor.

Emerging from the first stage reactor stream is diluted with acetone, applied at a rate of 8 ml/h, and served in the second stage reactor, heated to a temperature of 125°C. effluent from the second stage reactor stream is cooled and analyzed by GLC. The composition of the reaction mixture decomposition of the CCP are given in table 2.

Table 2
The composition of the reaction mass decomposition of CPC
ComponentConcentration, wt.%
Phenol40,69
Acetone41,89
Dicumylperoxide (DCT)0,28
Dimethylphenylcarbinol (DMPC)0,14
Cumylphenol0,37
The amount of dimers α-methylstyrene0,17
Acetophenon the 1,10
α-methylsterol (AMC)2,98
The cumeneof 10.72
Hydroxyacetone0,07
The oxide mesityl0,001
Unidentified0,67
Water0,92

Example 2.

The decomposition of the CCP produced on the same equipment as in example 1, but used as raw material mixture composition is shown in table 3.

The raw material is fed into the reactor at a rate of 10 ml/h, concentrated (96%) sulfuric acid is served with a speed of 0.55 ál/h, which corresponds to its concentration 0,009 wt.%, the phenol to the mixture with sulfuric acid served with a speed of 0.45 ál/h, which corresponds to the ratio of sulfuric acid/phenol of 2:1. A mixture of phenol and sulfuric acid was incubated for 600 minutes at a temperature of 20°C. the Speed of circulation of the reaction mixture of 200 ml/h Coming from the first stage reactor, the reaction mass is mixed with acetone, served with a speed of 3 ml/h, and served in the second stage reactor. The temperature in the reactor of the first stage 50°in the second stage reactor 140°C. the Composition of the reaction mass decomposition of CPC are shown in table 4.

Example 3.

The decomposition of the CCP produced on the same equipment and under the same conditions as in example 2, but for making katalizatorov reactor serves 30% oleum with a speed of 0.3 µl/h, and phenol with a speed of 600 μl/h (ratio in terms of sulphuric acid 1:1000). The residence time of the mixture in the reactor at a temperature of 80°C is 1 minute. The composition of the reaction mass decomposition of CPC are shown in table 4.

Example 4.

The decomposition of the CCP produced on the same equipment and under the same conditions as in example 1, but for the preparation of the catalyst in the reactor serves 75%sulfuric acid at the rate of 2 ál/h, and the phenol at a speed of 5 μl/h (ratio in terms of sulphuric acid 1:2). The residence time of the mixture in the reactor at a temperature of 60°With 80 minutes.

0,21
Table 3
Raw materials used for the decomposition of CPC
ComponentContent, wt.%
1Gasoperated cumene (CCP)80,46
2The cumene12,31
3Dimethylphenylcarbinol (DMPC)5,31
4The acetophenone0,54
5Water0,1
6Dicumylperoxide (DCT)0,61
7Phenol0,46
8Unidentified

The composition of the obtained reaction mass is presented in table 4.

Table 4
The composition of the reaction mixture decomposition of the CCP in examples 2-4
ComponentConcentration, wt.%
Example 2Example 3Example 4
Phenol40,8743,5940,67
Acetone44,6042,6244,63
Dicumylperoxide (DCT)0,020,040,09
Dimethylphenylcarbinol (DMPC)0,060,050,10
Cumylphenol0,160,130,18
The amount of dimers α-methylstyrene0,070,050,10
The acetophenone0,510,480,54
α-methylsterol (AMC)2,502,432,46
The cumeneof 10.219,5910,14
Hydroxyacetone0,060,050,09
The oxide mesityl0,01 0,01
Unidentified0,270,320,29
Water0,660,640,70

Example 5.

The decomposition of the CCP produced on the same equipment as in example 1, but used as raw material mixture composition is shown in table 5.

The raw material is fed into the reactor at a rate of 25 ml/h, concentrated (96%) sulfuric acid is served with a speed of 1.3 μl/h, which corresponds to its concentration 0,009 wt.%, the phenol to the mixture with sulfuric acid is served with rate of 3.4 ál/h, which corresponds to the ratio of sulfuric acid/phenol (1:1,5. A mixture of phenol and sulfuric acid was incubated for 140 minutes at a temperature of 42°C. the Speed of circulation of the reaction mixture of 200 ml/h Coming from the first stage reactor, the reaction mass is mixed with acetone, which is served with a speed of 11 ml/h, and water, which is served at a rate of 0.2 ml/h, which corresponds to 0.6% of the reaction mixture. The resulting mixture was fed into the second stage reactor. The temperature in the first stage reactor 40°in the second stage reactor 90°C. the Composition of the reaction mass decomposition of CPC are shown in table 6.

Table 5
Raw materials used for the decomposition of CPC
ComponentContent, wt.%
1Gasoperated cumene (CCP)82,73
2The cumene11,92
3Dimethylphenylcarbinol (DMPC)3,82
4The acetophenone0,52
5Water0,06
6Dicumylperoxide (DCT)0,64
7Phenol0,02
8Unidentified0,29

Table 6
The composition of the reaction mixture decomposition of the CCP in example 5
ComponentConcentration, wt.%
Phenol43,28
Acetone42,80
Dicumylperoxide (DCT)0,03
Dimethylphenylcarbinol (DMPC)0,08
Cumylphenol0,21
The amount of dimers α-methylstyrene0,11
The acetophenone0,47
α-methylsterol (AMC)2,23
The cumene8,87
hydroxyacetone 0,05
The oxide mesityl0,01
Unidentified0,92
Water0,94

Example 6.

The decomposition of the CCP produced on the same equipment as in example 1, but used as raw material mixture composition is shown in table 5.

The raw material is fed into the reactor at a rate of 25 ml/h, concentrated (96%) sulfuric acid is served with rate of 0.8 μl/h, which corresponds to its concentration 0,006 wt.%, the phenol to the mixture with sulfuric acid serves at a rate of 2.4 μl/h, which corresponds to the ratio of sulfuric acid/phenol (1:1,7. A mixture of phenol and sulfuric acid was incubated for 180 minutes at a temperature of 42°C. the Speed of circulation of the reaction mixture of 200 ml/h Coming from the first stage reactor, the reaction mass is mixed with acetone, which is served with a speed of 11 ml/h, and water, which is served with rate of 0.34 ml/h, which corresponds to 1% of the reaction mixture. The resulting mixture was fed into the second stage reactor. The temperature in the reactor of the first stage 50°in the second stage reactor 135°C. the Composition of the reaction mass decomposition of CPC are presented in table 7.

Table 7
The composition of the reaction mixture decomposition of the CCP in example 6
To the ponent Concentration, wt.%
Phenol43,11
Acetone42,53
Dicumylperoxide (DCT)0,09
Dimethylphenylcarbinol (DMPC)0,11
Cumylphenol0,22
The amount of dimers α-methylstyrene0,12
The acetophenone0,46
α-methylsterol (AMC)2,19
The cumene8,75
Hydroxyacetone0,05
The oxide mesityl0,01
Unidentified0,85
Water1,51

1. Method for production of phenol and acetone by acid-catalyzed decomposition of cumene hydroperoxide in the series connected reactors in two stages at an elevated temperature with simultaneous formation of the first stage of dicumylperoxide and its subsequent decomposition in the reaction medium in the second stage, wherein the process is carried out in the presence of a catalyst, which is prepared in a separate reactor prior to the introduction into the first reactor for the decomposition of cumene hydroperoxide by mixing sulfuric acid with phenol in a ratio of from 2:1 to 1:1000 and maintaining the resulting mixture at a temperature of 20-80° With over 1-600 minutes

2. The method according to claim 1, wherein the sulfuric acid has a concentration above 75% or use oleum.

3. The method according to claim 1, characterized in that in the second stage of decomposition of cumene hydroperoxide additionally served water in an amount up to 1% of the reaction mass.

4. The method according to claim 1, characterized in that in the first stage, keep the temperature from 40 to 75°and in the second stage, from 90 to 140°C.



 

Same patents:

FIELD: chemistry.

SUBSTANCE: invention relates to the method of obtaining phenol and acetone by acid-catalysable decomposition of hydro-peroxide of cumene in the environment of the reaction products at elevated temperatures in one stage. In this case the process is carried out in the presence of a catalyst, prepared immediately before its introduction into the reactor for the decomposition of hydro-peroxide of cumene by mixing sulfuric acid with phenol at the ratio of from 2:1 till 1:1000 and the waiting time from mixing till putting into the reactor for the decomposition of hydro-peroxide of cumene from 1 to 600 minutes at a temperature from 20 to 80°C. As a rule, sulfuric acid has a concentration of higher than 75% or oleum is used.

EFFECT: it makes it possible to decrease the output of the by-product hydroxyacetone, improves the quality of market-grade phenol and decreases the consumption of sulfuric acid.

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

SUBSTANCE: the invention is pertaining to the field of chemical industry, in particular, to the industrial process of production of phenol and acetone by the cumene method. The method is realized by decomposition of the technological cumene hydroperoxide in the in series connected reactors in two stages with formation on the first stage of the dicumylperoxide at the temperature of 40-65°С at presence as the catalytic agent of 0.003-0.015 mass % of the sulfuric acid with its subsequent decomposition on the second stage in the reaction medium at the temperature of 90-140°С. The process is conducted at the excess of phenol in the reaction mixture at the molar ratio of phenol : acetone exceeding 1, preferentially - from 1.01 up to 5. Excess of phenol is formed either by distillation (blowing) of acetone or addition of phenol in the reaction medium. The technical result of the invention is reduction of formation of hydroxyacetone, which one worsens the quality of the commercial phenol.

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

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FIELD: chemistry.

SUBSTANCE: invention relates to the method of obtaining phenol and acetone by acid-catalysable decomposition of hydro-peroxide of cumene in the environment of the reaction products at elevated temperatures in one stage. In this case the process is carried out in the presence of a catalyst, prepared immediately before its introduction into the reactor for the decomposition of hydro-peroxide of cumene by mixing sulfuric acid with phenol at the ratio of from 2:1 till 1:1000 and the waiting time from mixing till putting into the reactor for the decomposition of hydro-peroxide of cumene from 1 to 600 minutes at a temperature from 20 to 80°C. As a rule, sulfuric acid has a concentration of higher than 75% or oleum is used.

EFFECT: it makes it possible to decrease the output of the by-product hydroxyacetone, improves the quality of market-grade phenol and decreases the consumption of sulfuric acid.

2 cl, 4 tbl, 4 ex

FIELD: industrial organic synthesis.

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13 cl, 4 ex

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

SUBSTANCE: the invention is pertaining to the field of chemical industry, in particular, to the industrial process of production of phenol and acetone by the cumene method. The method is realized by decomposition of the technological cumene hydroperoxide in the in series connected reactors in two stages with formation on the first stage of the dicumylperoxide at the temperature of 40-65°С at presence as the catalytic agent of 0.003-0.015 mass % of the sulfuric acid with its subsequent decomposition on the second stage in the reaction medium at the temperature of 90-140°С. The process is conducted at the excess of phenol in the reaction mixture at the molar ratio of phenol : acetone exceeding 1, preferentially - from 1.01 up to 5. Excess of phenol is formed either by distillation (blowing) of acetone or addition of phenol in the reaction medium. The technical result of the invention is reduction of formation of hydroxyacetone, which one worsens the quality of the commercial phenol.

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, catalysts.

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8 cl, 24 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to a method for preparing phenol and acetone by acid-catalyzed cleavage of cumyl hydroperoxide. Method involves preliminary heating the reaction mixture to temperature above 100°C and then for thermal treatment of product heat in exothermic reaction is used, mainly the cleavage reaction of cumyl hydroperoxide that presents in the concentration from 5 to 10 wt.-%. The preferable residual content of dicumyl hydroxide in thermally treated product is 0.01-0.05 wt.-%. Stages in cleavage of cumyl hydroperoxide and the following thermal treatment can be carried out in a single reactor with two zones among that one zone is fitted with a device for heat removing and another zone has a feature of the flow-type pipe. Reactor is equipped by a device for circulation of part of product from thermal treatment zone to a feeding line for decomposition of product. Method provides improving energetic indices of process due to optimal consumption of heat energy in maintaining high selectivity of the decomposition process.

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EFFECT: increased selectivity of decomposition at lesser recycle apparatus volume and reduced investment expenses.

11 cl, 1 dwg, 9 ex

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,

,

in which M denotes a metal ion, or a combination of metal ions, corresponding to the elements belonging to group IB-VIIB or VIII of the Periodic table (CAS version), including the lanthanides; m is an integer from 1 to 6; p denotes an integer from 0 to 4; q represents an integer from 1 to 4; X represents an anion

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The invention relates to an improved method for production of phenol, acetone and-methylstyrene Kukolnik method and relates to the stage of acid decomposition of technical cumene hydroperoxide
The invention relates to the production of cycloalkanones C8-C12promising intermediates in the synthesis of lactams, aliphatic dicarboxylic acids, Daminov - monomers for the production of polyamide fibers, plastics and plasticizers new types and other valuable materials

FIELD: chemistry.

SUBSTANCE: invention pertains to the method of oxidation of hydrocarbons using oxygen in trifluoroacetic acid and can be used particularly for oxidation of alkanes, cycloalkanes, alkylaromatic hydrocarbons, alkenes, cycloalkenes. The method involves saturation of trifluoroacetic acid with oxygen, after which, the initial hydrocarbon is added to the obtained reaction medium and is kept until depletion of bound oxygen with obtaining the corresponding oxygen containing compound.

EFFECT: invention allows carrying out a process of selective partial catalytic oxidation of hydrocarbons with obtaining different oxygen containing organic compounds without use of high temperature and traditional catalyst systems based on transition metals.

1 tbl, 5 ex

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