WO2013012203A2 - Method of preparing cumyl alcohol and method of preparing phenol, acetone and alpha methyl styrene - Google Patents

Abstract

The present invention relates to a method of preparing cumyl alcohol and a method of preparing phenol, acetone and alpha methyl styrene. According to the present invention, through a hydrogenation process for cumene hydroperoxide obtained by oxidizing cumene in a phenol preparing process, selectivity may be improved and the amount of cumyl alcohol may be increased. In addition, the amount of the alpha methyl styrene may be selectively increased. Further, the produced amount of the alpha methyl styrene may be controlled according to market demand by controlling the amount of the cumene hydroperoxide.

Description

 【Specification】

 [Name of invention]

 Process for preparing cumyl alcohol and process for preparing phenol, acetone, and alpha methyl styrene

 Technical Field

 The present invention relates to a method for preparing cumyl alcohol and a method for preparing phenol, acetone, and alpha methyl styrene, and more particularly, to preparing cumyl alcohol capable of selectively increasing alpha methyl styrene without reducing the production of phenol. And to a process for the preparation of phenol, acetone, and alpha methyl styrene.

 This application is subject to the Korean Patent Application No. 10-2011-0070516 filed to the Korean Patent Office on July 15, 2011 and the Korean Patent Application No. 10-2011-0073166 filed to the Korean Patent Office on July 22, 2011. Claiming benefit, the entire contents of which are incorporated herein by reference.

 Background Art

 Alpha-methyl styrene is widely used as an additive in the manufacture of certain copolymers and novel polymers such as ABS. Alpha methyl styrene also has use as an intermediate for the preparation of fine compounds such as unsaturated alpha methyl styrene dimers. These dimers have been used as molecular weight control agents in the preparation of copolymers such as acrylonitrile-butadiene-styrene resins and styrene-butadiene rubbers. The hydrogenated form of alpha methyl styrene dimer has industrial value as a component in lubricating compositions.

 Such alpha methyl styrene is generally produced as a by-product of the phenol production process for producing phenol through oxidation and dehydration processes using cumene as a raw material.

 1 is a process diagram briefly showing a conventional phenol production process.

Referring to FIG. 1, a stream in which cumene is oxidized in the presence of oxygen in a cumene-supplied oxygen reactor (1) is converted into cumene hydroperoxide and a small amount of cumyl alcohol in an amount of about 24% by weight. ) Containing about 24% by weight of cumene hydroperoxide in the stripper (3) The stream is concentrated to 82 weight percent. The concentrated cumene hydroperoxide and cumyl alcohol containing streams are then fed via a reservoir (4) to a cracking reaction vessel (5) to dehydrate under acid catalyst to produce phenol and acetone from cumene hydroperoxide and also from cumyl alcohol Produces alpha methyl styrene. However, since the cumyl alcohol is only 0.035 mole per 1 mole of cumene hydroperoxide in the cumene oxidation process, the production amount of alpha methyl styrene in the phenol manufacturing process is reduced to the small amount of cumyl alcohol produced in the cumene oxidation process. Are limited by

 Therefore, research has been conducted to selectively increase the production of alpha methyl styrene.Also, a portion of cumene hydroperoxide from the stripper before the cleavage reactor is selectively converted to cumyl alcohol to alpha methyl. There is a way to increase styrene. However, the method has a low conversion rate and selectivity, lowers the process efficiency, and has a problem of stability due to the use of highly concentrated cumene hydroperoxide.

 In addition, the conventional method discloses a method of converting the hydrogenation process of the alpha methyl styrene produced for recycling to the reaction reaction group back to cumene, not mainly for the purpose of increasing the alpha methyl styrene (US Pat. No. 5,905,178). Or, by treating alpha methyl styrene as a by-product of the phenol production process, attempts to minimize the production of alpha methyl styrene are mainly made (US Pat. No. 5,530,166). However, there is insufficient research to increase the production of alpha methyl styrene. to be.

 [Content of invention]

 [Issue to solve]

 In order to solve the above problems, the present invention provides a method for producing cumyl alcohol and phenol that can selectively increase the alpha methyl styrene was considered as a by-product in the phenol production process by hydrogenation from cumene hydroperoxide to cumyl alcohol To provide acetone, and a method for producing alpha methyl styrene.

[Measures of problem] Accordingly, the present invention provides a process for preparing cumyl alcohol in which hydrogenation of cumene hydroperoxide is carried out under a Pd-Co catalyst.

 In addition, the present invention,

 (a) oxidizing cumene to produce a cumene hydroperoxide stream;

 (b) separating at least ¾ parts of the cumene hydroperoxide stream and hydrogenating under Pd-Co catalyst to produce cumyl alcohol;

 (c) dewatering the reaction product comprising the cumyl alcohol; And (d) dehydrating the remaining portion of the cumene hydroperoxide stream not subjected to the hydrogenation reaction.

 According to an embodiment of the present invention, the steps (c) and (d) may be performed simultaneously in the same reaction period.

 According to another embodiment of the present invention, the steps (c) and (d) may be performed separately in a separate reaction period.

 According to one embodiment of the present invention, the weight ratio of Pd: Co in the Pd-Co catalyst may be 1: 0.05 to 1: 1.

 According to an embodiment of the present invention, in the step (c), the semi-ungmul containing cumyl alcohol may be dehydrated under an acidic catalyst.

 According to one embodiment of the present invention, in the step (c), the semi-ungmul containing cumyl alcohol may be dehydrated under a resin catalyst.

According to one embodiment of the invention, in step (a), the cumene hydroperoxide stream may be produced at a concentration of 5 to 25% by weight. Also, according to another embodiment of the present invention in step (b), cumene hydroperoxide switch: by separating the stream of 5 to 50 parts by weight _^0/0 can be used in the hydrogenation banung.

In the production method according to the method of the present invention, when the hydrogenation reaction is performed for 3 hours, the selectivity of the hydrogenation reaction may be 95% or more, and the conversion of cumene hydroperoxide to cumyl alcohol may be 80% or more. Hereinafter, a method of preparing cumyl alcohol of the present invention and a method of preparing phenol, acetone, and alpha methyl styrene will be described in more detail. Process for preparing cumyl alcohol

 Method for producing cumyl alcohol of the present invention is cumene hydroperoxide Pd-

Hydrogenation under Co catalyst to produce cumyl alcohol.

 The use of Pd-Co catalysts in the hydrogenation of cumene hydroperoxide can convert cumene hydroperoxide to cumyl alcohol with high conversion and selectivity.

The hydrogenation reaction may be performed at a temperature of about 40 to about 80 ^° C for about 0.2 to about 7 hours, but is not limited thereto. The hydrogenation reaction can also be carried out under conditions of normal fluid space velocity.

 The hydrogenation. The reaction can be carried out by adding about 1 to about 10 moles of hydrogen with respect to 1 mole of cumene hydroperoxide in conventional reaction groups well known in the art. At this time, if the added mole number of hydrogen is less than 1 mole, there is a problem that the conversion and selectivity is lowered.

 The Pd-Co catalyst may further include a carrier selected from the group consisting of alumina, silica, clay, carbon, zirconia, titania, mesoporous molecular sieves, and combinations thereof.

 According to one embodiment of the present invention, the Pd-Co catalyst is preferably used a Pd-Co / C catalyst containing carbon as a carrier.

 According to one embodiment of the present invention, the Pd-Co catalyst may be used in an amount of 0.5 to 15 parts by weight based on 100 parts by weight of cumene hydroperoxide stream at a concentration of 25% by weight. When the amount of the Pd-Co catalyst is 5 to 15 parts by weight, it may exhibit high conversion and selectivity. .

In addition, the weight ratio of Pd: Co in the Pd-Co catalyst of the present invention may be 1: 0.05 to 1: 1, preferably 1: 0.2 to 1: 0.5. In particular, when the weight ratio of Pd: Co is 1: 0.2, conversion to cumyl alcohol can be achieved with the highest conversion and selectivity within the same hydrogenation reaction time. According to the production method of the present invention, since the hydrogenation process of cumene hydroperoxide is carried out under mild conditions, it reduces the risk of explosion at runway reaction temperature of cumene hydroperoxide to increase the conversion to cumyl alcohol under the most stabilized conditions. Can be.

 The selectivity of the hydrogenation reaction in the method for producing cumyl alcohol of the present invention is

95% or more, more preferably 98% or more. In the case of the conventional catalyst reduction (catalyst reduction) method, the conversion is up to 20 to 35%, the selectivity is 80%, the maximum yield is not 40%, whereas the hydrogenation process according to the production method of the present invention is about 3 Cumyl alcohol can be obtained at a conversion rate of at least 80%, at least 95% of selectivity, and at least 80% of yield within a time of hydrogenation reaction time. At least 99% of conversion, at least 98% of selectivity, and yield 98 of about 4 hours of hydrogenation reaction time. Cumyl alcohol can be obtained by more than%. Furthermore, cumyl alcohol can be obtained with a conversion rate of substantially 100% as the reaction time is increased. Process for preparing phenol, acetone, and alpha methyl styrene

 Method for producing phenol, acetone, and alpha methyl styrene of the present invention,

 (a) oxidizing cumene to produce a cumene hydroperoxide stream; (b) separating at least a portion of the cumene hydroperoxide stream and hydrogenating it under a Pd-Co catalyst to produce cumyl alcohol; (c) dewatering the reaction product comprising the cumyl alcohol; And (d) dewatering the remaining portion of the cumene hydroperoxide stream that has not undergone the hydrogenation reaction.

In general, a phenol manufacturing process is the cumene level of 25 weight _^0/0 produced through an oxidation banung hydroperoxide (CHP) solution through the stripper concentrated to CHP solution of 80 increased _^0/0, and phenol through an exploded banung, acetone , And a process for producing alpha methyl styrene.

By the way, cumene hydroperoxide has a flash point of 57 to 79 ^° C, it is explosive when mixed with air. Furthermore, there is a risk of explosion and fire upon contact with organic materials, acids, bases and metals. In addition, as the concentration of cumene hydroperoxide increases, the runway reaction temperature decreases, which may cause an explosion hazard. There is a report of increase (Thermochimica acta, 501, 2010, 65-71). Therefore, there is a need for a method for performing a phenol plant in a stable manner without using a high concentration of Cuman hydroperoxide as described above. The production method of the present invention provides a process capable of producing cumyl alcohol in a stable state using a low concentration of cumene hydroperoxide.

 For this reason, it is very important that the conversion process of cumene hydroperoxide is carried out at maximum stabilized conditions, that is, at a low cumene hydroperoxide concentration and at a low temperature.

 In addition, in the conventional phenol manufacturing process, cumyl alcohol has only about 0.035 moles of cumene hydroperoxide 1, thereby limiting the production of alpha methyl styrene.

 According to the production method of the present invention, after increasing the yield of cumyl alcohol through the hydrogenation process of cumene hydroperoxide to cumyl alcohol, it is possible to increase the production of alpha methyl styrene by dehydrating the cumyl alcohol. That is, in the prior art, while the cumene hydroperoxide stream obtained by the oxidation of cumene is concentrated in a stripper and then dehydrated as it is in a decomposition reactor, the method of the present invention provides the oxidation in a low concentration state before concentration in a stripper. By separating a part of cumene hydroperoxide obtained after the reaction and using it in the hydrogenation process, the selectivity of cumene hydroperoxide and conversion to cumyl alcohol can be improved.

 Therefore, the production method of the present invention shows a much better result than the conventional by converting cumene hydroperoxide to cumyl alcohol in the region of low concentration stability is secured in the production process. In other words, in the production method of the present invention, the cumene hydroperoxide stream before passing through the stripper into the cleavage reactor is not used as a reaction counterpart of the hydrogenation reaction reaction, but the cumene hydroperoxide after cumene oxidation is used. Ensure stability of the process.

In the preparation method of the present invention, first, cumene is oxidized to produce a cumene hydroperoxide stream (step (a)). According to one embodiment of the invention, through the steps of: (a) the process of, the hydroperoxide stream of cumene in the range of about 5 to about 25 parts by weight _^0/0 concentration can be produced eu also the oxidation of the cumene while the stream Via a small amount of cumyl alcohol.

At this time, the oxidation conditions in step (a) is not particularly limited, and may be performed under general conditions. For example, the oxidation of cumene can usually be carried out by automatic oxidation with an oxygen-containing gas such as air or oxygen enriched air. The oxidation reaction can also be carried out with or without additives such as alkalis. The additives include alkali metal compounds such as sodium hydroxide (NaOH), potassium hydroxide (KOH), alkaline earth metal compounds, alkali metal carbonates such as sodium carbonate (Na ₂ CO ₃ ), sodium hydrogen carbonate (NaHC0 ₃ ), ammonia, ammonium carbonate Etc. may be used, but the present invention is not limited thereto. According to one embodiment of the present invention, the oxidation reaction can be carried out at a pressure of about 50 to about 200 ^° C and a atmospheric pressure of about 5 MPa.

 In addition, the oxidation of cumene in step (a) may be carried out through a plurality of oxidation reaction groups, preferably three oxidation reaction groups used in a conventional phenol process. Further, step (a) may oxidize a cumene containing stream having a cumene concentration of at least 80%, preferably at least 98% in the presence of an oxygen containing stream to form a cumene hydroperoxide containing stream.

 According to one embodiment of the invention, conventional initiators may be used to promote oxidation of the cumene. The initiator may be an organic hydroperoxide such as cumene hydroperoxide, t-butyl hydroperoxide, a peroxy free radical initiator, an azo free radical initiator, or the like, but is not limited thereto.

 Next, at least a part of the cumene hydroperoxide stream prepared in step (a) is separated and reacted with hydrogen under a Pd-Co catalyst to prepare cumyl alcohol (step (b)).

Part of the cumene hydroperoxide stream separated in step (b) is converted to cumyl alcohol and then produces alpha methyl styrene, thus hydrogenating The amount of alpha methyl styrene can be controlled by appropriately adjusting the proportion of the cumene hydroperoxide stream used in the reaction. According to one embodiment of the invention, a portion of the cumene hydroperoxide stream, preferably about 5 to about 50% by weight, can be separated and used for the reaction.

 In addition, according to one embodiment of the present invention, the cumene hydroperoxide stream may be subjected to a hydrogenation reaction by separating at least a portion without concentration. In the hydrogenation reaction, cumene hydroperoxide can be converted into cumyl alcohol with high conversion and selectivity by using a Pd-Co catalyst. In addition, by using the Pd-Co catalyst it is possible to shorten the time to convert cumene hydroperoxide to cumyl alcohol to enjoy the entire process time.

 The Pd-Co catalyst may further include a carrier selected from the group consisting of alumina, silica, clay, carbon, zirconia, titania, mesoporous molecular sieves, and combinations thereof. According to one embodiment of the invention, the Pd-Co catalyst may be a Pd-Co / C catalyst containing carbon as a carrier.

 According to one embodiment of the present invention, the Pd-Co catalyst may be used in an amount of about 0.5 to about 15 parts by weight based on 100 parts by weight of cumene hydroperoxide stream having a concentration of 25% by weight. When the amount of the Pd-Co catalyst is 0.5 to 15 parts by weight, it may exhibit high conversion and selectivity.

 In addition, the weight ratio of Pd: Co in the Pd-Co catalyst of the present invention may be 1: 0.05 to 1: 1, preferably 1: 0.2 to 1 :(). 5. In particular, the weight ratio of Pd: Co is 1: 0.2. The conversion to cumyl alcohol can be achieved at the highest conversion and selectivity within a certain hydrogenation reaction time.

The hydrogenation reaction may be performed for about 0.2 to about 7 hours at a temperature condition of about 40 to about 80 ^° C. The hydrogenation reaction can also be carried out under conditions of ordinary fluid space velocity.

In addition, the hydrogenation reaction may be performed by adding about 1 to about 10 moles and hydrogen per 1 mole of cumene hydroperoxide. At this time, if the number of moles of hydrogen added is less than 1 mole, there is a problem of low conversion and selectivity. If exceeded, excessive amounts of hydrogen must be recycled, which may cause economic problems.

 According to the preparation method of the present invention, the process of hydrogenation of cumene hydroperoxide is carried out under mild conditions, so the runway reaction of cumene hydroperoxide may reduce the explosion risk of the city and increase the conversion to cumyl alcohol under the most stabilized conditions. In addition, high concentrations of cumene hydroperoxide can be converted to cumyl alcohol, thereby increasing the alpha methyl styrene content in subsequent steps.

 Selectivity of the hydrogenation reaction in the production method of the present invention may be 95% or more, more preferably 98% or more. In the conventional catalyst reduction method, the conversion rate is 20 to 35%, the selectivity is 80%, and the maximum yield is not 40%, whereas the hydrogenation process of the present invention is about 3 hours. Cumyl alcohol can be obtained with a conversion rate of 80%, a selectivity of 95%, and a yield of 80% or more within a hydrogenation reaction time, and a conversion rate of 99%, a selectivity of 98%, and a yield of 98% or more within a hydrogenation reaction time of about 4 hours. Cumyl alcohol can be obtained. Increasing the reaction time can also yield cumyl alcohol with substantially 100% conversion. In addition, cumene, which is mixed with cumene hydroperoxide in the hydrogenation process, may be converted to some cumyl alcohol, and thus, further yield improvement may be expected.

 Next, the reaction product containing the cumyl alcohol is dehydrated (step (c)), and the remaining portion of the Coman hydroperoxide stream which has not undergone the hydrogenation reaction is dehydrated (step (d)).

 Step (c) is a step of obtaining alpha methyl styrene by dehydration reaction of cumyl alcohol. In addition, step (d) is a step of obtaining phenol and acetone by dehydration reaction of cumene hydroperoxide. .

 According to an embodiment of the present invention, the steps (c) and (d) may be performed simultaneously in the same reaction period.

When carrying out steps (c) and (d) simultaneously, the cumyl alcohol subjected to the hydrogenation reaction and the remainder of the cumene hydroperoxide stream not subjected to the hydrogenation reaction are mixed to proceed with dehydration in the form of a mixture. At this time The mixture comprising the cumyl alcohol and cumene hydroperoxide stream is

Concentration at a concentration of 80 to 82% by weight may proceed to dehydration reaction.

 According to an embodiment of the present invention, in the step (c), the semi-ungmul containing cumyl alcohol may be dehydrated under acidic catalyst.

 Further, in step (d), the remainder of the cumene hydroperoxide stream that has not undergone the hydrogenation reaction can be dehydrated under acidic catalyst.

 The acidic catalyst may be a liquid or solid acidic catalyst. The liquid acidic catalyst is hydrochloric acid, sulfuric acid or nitric acid, preferably sulfuric acid can be used. The solid acidic catalyst is also selected from the group consisting of Group 4 metal oxides modified by Group 6 metal oxides, sulfated transition metal oxides, mixed metal oxides of cerium oxides and Group 4 bimetallic oxides, and mixtures thereof. desirable.

 According to another embodiment of the present invention, in the step (c), the semi-ungmul containing cumyl alcohol may be dehydrated under a resin catalyst.

 Further, in the step (d), the remaining portion of the cumene hydroperoxide stream that has not undergone the hydrogenation reaction can be dewatered under a resin catalyst.

The resin catalyst may be, for example, a polystyrene-based cation exchange resin, it is preferable to use a sulfonated polystyrene-based cation exchange resin catalyst. The ^'it is a resin containing a sulfonic acid group at various concentrations in the polystyrene-based cation exchange resin can be appropriately selected. For example, a cation exchange resin having a concentration of sulfonic acid group of about 30 to 60% can be used. In addition, the dehydration reaction using the resin catalyst may be performed for about 0.2 to about 7 hours at a temperature condition of about 50 to about 90 'C, but the present invention is not limited thereto.

By carrying out the dehydration of cumyl alcohol under the resin catalyst, there is an additional advantage that alpha methyl styrene can be produced with higher conversion and selectivity. Also, the product may further include trace amounts of acetophenone, cumene, and heavy compounds. In step (b) and residues of the remaining streams except the cumene hydroperoxide stream used in the hydrogenation reaction of step (b), before performing step (c) to minimize the production of heavy compounds, if necessary. The obtained mixture of cumyl alcohol can also be diluted. According to another embodiment of the present invention, step (c) and step (d) may be performed separately in a separate reaction period.

 That is, the dehydration of cumyl alcohol converted by hydrogenation reaction and the dehydration of cumene hydroperoxide without hydrogenation may be performed in separate physically separated reactors.

 Accordingly, the detailed process conditions of the dehydration process for producing phenol and acetone and the dehydration process for producing alpha methyl styrene can be optimized and set differently, so that there is an additional advantage of increasing both the yield of phenol and alpha methyl styrene. .

 For example, according to one embodiment of the present invention, the dehydration reaction of cumyl alcohol may be performed under a resin catalyst, and the remainder of the cumene hydroperoxide stream which has not undergone the hydrogenation reaction may be dewatered under acidic catalyst. In this case, the resin catalyst used for dehydration reaction of cumyl alcohol may be used in an amount of about 1 to about 10 parts by weight based on 100 parts by weight of cumyl alcohol. In addition, when the dehydration reaction is carried out under acidic catalyst to the remainder of the cumene hydroperoxide stream, it is preferable to undergo a neutralization reaction, but for the dehydration reaction of the cumyl alcohol, a resin catalyst is used to undergo a neutralization reaction after the dehydration reaction. no need.

 According to one embodiment of the present invention, the remaining portion of the cumene hydroperoxide stream not subjected to the hydrogenation reaction may be concentrated to proceed with dehydration reaction. ,

If the dehydration process is carried out in this way, there is an advantage that can increase the production of alpha methyl styrene without reducing the production of phenol and acetone as the main product. In the dehydration process, when cumene hydroperoxide and cumyl alcohol coexist in one reaction period, The reaction has the additional advantage of preventing the production of by-products. For example, the amount of time to perform separating and dewatering step the impurity is less than 7% by weight based on the total amount of phenol, acetone and alpha methyl styrene, may be less than 5 parts by weight and preferably ^_0/0.

 After step (c) and step (d), it may further comprise the step of purifying the product containing the phenol, acetone and alpha methyl styrene and separating by distillation. Through this process, alpha methyl styrene, phenol, and acetone can each be separated.

 The purification step can be used under ordinary conditions. In addition, the distillation conditions are not particularly limited and may be made through a conventional method. Next, a method for preparing phenol, acetone and alpha methyl styrene according to one embodiment of the present invention will be described in more detail with reference to the accompanying drawings. 2 is a simplified illustration of a process for producing phenol, acetone, and alpha methyl styrene in accordance with one embodiment of the present invention.

Referring to FIG. 2, the method of the present invention comprises: an oxidation reaction reactor 10 for proceeding oxidation of cumene; A hydrogenation reactor 30 for using a portion of the cumene hydroperoxide stream obtained after the oxidation in a hydrogenation reaction; The hydrogenation stripper for concentrating the cumyl alkoeul and the remaining cumene hydroperoxide stream has not been used in the hydrogenation reaction resulting in banung _(S tripper) (40); A cleavage reactor 60 for proceeding with dehydration reaction of the complex concentrated in the stripper; A refining apparatus (70) for purifying the product obtained by the dehydration reaction; And a separation device 80 for separating the product. In addition, reservoirs 20 and 50 may be provided between the oxidation reaction reactor 10 and the stripper 40, and between the stripper 40 and the decomposition reaction reactor 60.

Specifically, the present invention produces cumene hydroperoxide and cumyl alcohol having a low concentration by the oxidation of cumene, and at least a portion of the cumene hydroperoxide is directly reacted without hydrogenation to produce cumyl alcohol, the hydrogenation reaction when used Un Cumen By mixing the remaining residues of hydroperoxide and cumyl alcohol obtained by the hydrogenation reaction to prepare a reflux containing cumyl alcohol, and dewatering it, a product containing alpha methyl styrene having increased productivity is obtained. Can be. Since the product also contains phenol and acetone, the product is purified and distilled after the step to obtain alpha methyl styrene with increased productivity with phenol and acetone. Therefore, through the hydrogenation process of cumene hydroperoxide, the conversion rate of cumene hydroperoxide to cumyl alcohol can be improved and the content thereof can be increased or decreased, and the amount of alpha methyl styrene can be increased or decreased. have. That is, the present invention feeds cumene to the reaction vessel 10 and proceeds the reaction reaction of cumene in the presence of oxygen. According to one embodiment of the present invention, although not shown in the figure, the oxidative reaction reactor 10 may be provided with a plurality of oxidation reactions in stages. For example, the reaction may proceed in three stages in three oxidation reactors. In the oxidation reactor 10, a stream of cumene hydroperoxide of from 5 to 25 parts by weight _^0/0 concentration is generated through the oxidation of the cumene, this may contain a small amount of cumyl alkoeul.

 Thereafter, the present invention separates a part of the stream and transfers the reservoir 20 to the hydrogenation reactor 30 to proceed with the hydrogenation reaction. At this time, the low concentration of cumene hydroperoxide stream conveyed to the reservoir 20 is fed to the top-down or bottom-up of the catalytic hydrogenation reaction reactor 30 to produce cumyl alcohol with hydrogenation reaction. . The reaction vessel used for the hydrogenation reaction is

The reaction may proceed through a CSTR continuous stirred-tank reactor, but the present invention is not limited thereto, and any reaction may be used as long as it is used under ordinary hydrogenation reaction conditions. For example, it is preferable that the catalyst is layered in the hydrogenation reactor 30, and reaction is performed by injecting hydrogen and maintaining the internal temperature. According to an embodiment of the present invention, the hydrogenation reaction reactor ₃₀ has a _Pd .

The reaction can be carried out by charging the Co / C catalyst. In addition, the concentrated cumene hydroperoxide stream may be injected into the top of the reaction vessel using a pressure pump. By the hydrogenation reaction cumene hydroperoxide was converted to cumyl alcohol. When the hydrogenation reaction is completed, the produced cumyl alcohol is supplied back to the reservoir 20, and is transferred to the stripper 40 through it. In addition, the remaining stream of cumene hydroperoxide that has not undergone the hydrogenation reaction is sent directly to stripper 40.

 Accordingly, stripper 40 contains a small amount of cumyl alcohol by oxidation of cumene in the remaining stream of cumene hydroperoxide not used for hydrogenation reaction and cumene in the reaction vessel 10, in addition to cumyl alcohol obtained by the hydrogenation reaction. Includes the complex.

Thereafter, the stripper 40 ^' concentrates the mixture and passes through the reservoir 50 to the decomposition reaction vessel 60. According to one embodiment of the invention, the mixture may be concentrated to a concentration of 80 to 82% by weight.

 Then, dehydration reaction is performed on the mixture in the decomposition reaction device 60 to decompose cumene hydroperoxide into phenol and acetone, and decompose cumyl alcohol with alpha methyl styrene. According to one embodiment of the present invention, the decomposing reaction device 60 may be filled with an acidic catalyst or a resin catalyst to perform dehydration reaction.

 The mixture of phenol, acetone and alpha methyl styrene produced in the decomposition reaction reactor 60 is transferred to the purification apparatus 70 to proceed with the purification reaction.

 Finally, the purified mixture is transferred to a separation device 80 and separated by distillation into phenol, acetone and alpha methyl styrene, respectively.

 The phenol, acetone and alpha methyl styrene that are finally separated can be collected into a collection reservoir through separately connected outlets.

 At this time, in the present invention, the reactor used for each reaction step is not particularly limited in its condition, it is possible to use a conventional reaction reaction well known in the art. In addition, each semi-unggi can be connected through a separate transfer line. A method for preparing phenol, acetone and alpha methyl styrene according to another embodiment of the present invention will be described in more detail with reference to the accompanying drawings.

Figure 3 is a simplified view of a process for producing phenol, acetone and alpha methyl styrene according to an embodiment of the present invention. Referring to Figure 3, the method of the present invention, the oxidation reaction step for proceeding the oxidation of cumene (100); A hydrogenation reactor 300 for using a portion of the cumene hydroperoxide stream obtained after the oxidation in a hydrogenation reaction; A stripper 400 for concentrating the remaining cumene hydroperoxide stream not used in the hydrogenation reaction; A first cleavage reactor 320 for proceeding with dehydration of cumyl alcohol obtained by the hydrogenation reaction; A second cleavage reactor 600 for proceeding dehydration of the remaining cumene hydroperoxide stream not used for the hydrogenation reaction in the stripper; A neutralization apparatus 700 for proceeding neutralization of the product obtained from the second decomposition reactor 600; And a separation apparatus 800 for separating the products. In addition, receivers 200 and 500 may be further provided between the oxidation reaction reactor 100 and the stripper 400, and between the stripper 400 and the second decomposition reaction reactor 600. In addition, a reservoir 310 may be further provided between the hydrogenation reaction vessel 300 and the first decomposition reaction reactor 320.

 Specifically, the present invention produces cumene hydroperoxide and cumyl alcohol having a low concentration by the oxidation of cumene, and at least a portion of the cumene hydroperoxide is directly reacted without hydrogenation to produce cumyl alcohol, which is then dehydrated under a resin catalyst. By reacting and separately dehydrating the remaining portion of cumene hydroperoxide that was not used in the hydrogenation reaction, a product containing phenol, acetone and alpha methyl styrene with increased productivity can all be obtained.

That is, after the step of producing phenol and acetone by dehydration reaction from cumene hydroperoxide and the step of producing alpha methyl styrene by dehydration reaction from cumyl alcohol, after the step ^' phenol, acetone and alpha methyl By combining, purifying and separating the products of styrene, it is characterized by obtaining alpha methyl styrene with increased productivity at the same time without decreasing the production of the main products phenol and acetone. In addition, the decomposition reaction of cumyl alcohol and cumene hydroperoxide independently in the spatial separation state As it proceeds, there is no fear of by-products caused by these reactions, and the content of total impurities is lowered.

More specifically with reference to FIG. 3, first, cumene is supplied to the oxidative reaction reactor 100 to perform an oxidation reaction of cumene in the presence of oxygen. According to one embodiment of the present invention, although the reaction reactor 100 is not shown in the drawing, a plurality of dogs may be provided in step by step oxidation reaction. For example, the oxidation reaction may be performed in three stages in three oxidation reactions. Oxidation of the cumene produces a cumene hydroperoxide ^' stream at a concentration of 5 to 25% by weight.

 Thereafter, the present invention separates a part of the cumene hydroperoxide stream and supplies it to the hydrogenation reactor 300 via the reservoir 200 to proceed with the hydrogenation reaction. The low concentration cumene hydroperoxide stream sent to reservoir 200 can feed catalyst to the top-down or bottom-up of hydrogenation reactor 300 to produce cumyl alcohol as a hydrogenation reaction. The reaction vessel used for the hydrogenation reaction may be subjected to reaction through a CSTR reaction reactor, but is not limited thereto, and any reaction may be used as long as it is used under ordinary conditions of hydrogenation reaction. For example, it is preferable that the catalyst is layered in the hydrogenation reaction reactor 300, and reaction is performed by injecting hydrogen and maintaining the internal temperature. According to an embodiment of the present invention, the reaction may be performed by layering a Pd-Co / C catalyst on the hydrogenation reaction reactor 300. In addition, the concentrated cumene hydroperoxide stream may be injected into the top of the reaction counter using a pressurized pump. The hydrogenation reaction converts the cumene hydroperoxide to cumyl alcohol.

_. When the hydrogenation reaction is completed, the prepared cumyl alcohol is supplied back to the low-term (310), and is transferred to the first decomposition reaction vessel (320). Dehydration reaction to alpha methyl styrene is performed in the first decomposition reactor 320. According to one embodiment of the invention, the dehydration and reaction can be carried out using an acid catalyst. Alternatively, according to another embodiment of the present invention, the dehydration reaction may be performed using a resin catalyst. For example, cumyl is passed through the cumyl alcohol in the first cracking reactor 320 immobilized via a beads or the like. The alcohol undergoes a decomposition reaction to produce a product comprising alpha methyl ethylene.

 The product comprising alpha methyl ethylene produced in the first cracking reactor 320 is then combined with the product comprising phenol and acetone via the second cracking reactor 600 and the neutralizer 700 described below.

 The remaining stream of cumene hydroperoxide that has not undergone the hydrogenation reaction is sent directly to stripper 400. Accordingly, the stripper 400 includes cumene hydroperoxide not used in the hydrogenation reaction. The stripper 400 may also include small amounts of cumyl alcohol obtained by the oxidation of cumene.

 Then, dehydration reaction is performed on the cumene hydroperoxide in the second decomposition reactor 600 to decompose the cumene hydroperoxide into phenol and acetone. According to one embodiment of the present invention, the dehydration reaction in the second decomposition reaction reactor 600 may be performed under an acidic catalyst. Reaction conditions such as temperature, pressure, reaction time, catalyst type, and catalyst amount in the first decomposition reaction reactor 320 and the second decomposition reaction reactor 600 may be independently set.

 Accordingly, the product containing phenol and acetone produced in the second decomposition reaction step 600 is transferred to the neutralization device 700 to perform a neutralization process.

 Next, the product comprising the phenol and acetone, which have undergone the neutralization process, and the product containing alpha methyl styrene produced in the first cracking reaction step 320, are combined and transferred to the separation device 800. Separation device 800 separates into phenol, acetone and alpha methyl styrene, respectively, through purification and distillation. The final separated phenols, acetone and alpha methyl styrene can also be collected into collection reservoirs through separate connected outlets.

According to the production method according to an embodiment of the present invention as described above, after the step of producing phenol and acetone from cumene hydroperoxide and the step of generating alpha methyl styrene from cumyl alcohol separately, after the step By combining, purifying and separating the products, alpha methyl increases productivity simultaneously without reducing the production of the main products phenol and acetone. You can get styrene. In addition, since cumyl alcohol and cumene hydroperoxide are separated from each other in the process, there is no fear of byproducts caused by their reaction, so that the total impurities are lowered and subsequent purification processes can be simplified to reduce production costs. Can be.

【Effects of the Invention】

 The present invention proceeds to the hydrogenation reaction of cumene hydroperoxide obtained by the oxidation of cumene at the most stabilized conditions of low concentration and low temperature, it is possible to produce cumyl alcohol in a more stable state without the explosion risk of cumene hydroperoxide. In addition, the present invention can produce alpha methyl styrene with high selectivity and conversion through a dehydration process using a hydrogenation process using a Pd-Co catalyst.

 Further, according to one embodiment of the present invention, alpha methyl styrene can be produced with higher conversion and selectivity by performing dehydration of cumyl alcohol under a resin.

 In addition, according to an embodiment of the present invention, by separating the process for producing alpha methyl styrene from cumyl alcohol and the process for producing phenol and acetone from cumene hydroperoxide, impurities are reduced and the main products of phenol and acetone It is possible to increase the production of alpha methyl styrene without decreasing the yield.

 [Brief Description of Drawings]

 1 is a process diagram briefly illustrating a conventional phenol production process.

 2 is a process diagram briefly illustrating a process for producing phenol, acetone and alpha methyl styrene according to an embodiment of the present invention.

 3 is a process diagram briefly illustrating a process for producing phenol, acetone and alpha methyl styrene according to an embodiment of the present invention.

 4 is a graph showing the conversion rate of cumene hydroperoxide, the selectivity and yield of cumyl alcohol according to the method for preparing cumyl alcohol of Examples 1 to 5;

 [Specific contents to carry out invention]

 Hereinafter, through the specific examples of the invention, it will be described in more detail the operation and effects of the invention. However, these embodiments are only presented as an example of the invention, whereby the scope of the invention is not determined.

<Manufacture of cumyl alcohol> Example 1

 The reaction was carried out by filling the hydrogenation reactor with Pd-Co / C as a catalyst, injecting hydrogen and maintaining the internal temperature. The reaction product was injected with a cumene hydroperoxide stream at a concentration of 25% by weight using a pressure pump. The hydrogenation reaction was carried out by injecting 150 g of cumene hydroperoxide (CHP) at a concentration of 25% by weight and Pd-Co / C catalyst lg having a weight ratio of 1: 1 to Pd: Co. In addition, the molar ratio of cumene hydroperoxide stream and injected hydrogen was maintained at 1: 8. The reaction time was 3 hours. Examples 2-5

 It carried out similarly to Example 1 except having used the Pd-Co / C catalyst which changed the weight ratio of Pd: Co. The weight ratio of Pd: Co is shown in Table 1 below.

 TABLE 1

Preparation of Phenol, Acetone and Alpha Methyl Styrene

 Example 6

 Phenol, acetone and alpha methyl styrene were prepared according to the process diagram shown in FIG.

 First, the oxidation of cumene using an oxidizing agent was carried out using three oxidation reaction groups in a phenol process to prepare a stream including cumene hydroperoxide (CHP) at a concentration of 25% by weight.

(1) Conditions under which the first oxidizer is added Supply (CHP 0.4% + Cumene 99.6%) 1 ml / min, 02: 100 ml / min, pressure: 3 bar, reaction temperature: 100 ^° C

 (2) the condition of adding a second oxidizer

 Supply (CHP 8.42% + Cumene 91.58%) 1 ml / min, 02: 100 ml / min, pressure: 3 bar, reaction temperature: 96

 (3) the condition of adding a third oxidizer

 Supply (CHP 16.27% + Cumene 83.73%) 1 ml / min, 02: 100 ml / min, pressure: 3 bar, reaction temperature: 94 ° C

 At this time, the concentration of the CHP stream was changed to 8.4 to 24% by weight through three oxidation reactions.

Thereafter, 25 weight ⁰ /. Of the low concentration stream was separated and transferred to the low organ 20, and then supplied to the hydrogenation reaction vessel 30.

The hydrogenation reaction was filled with Pd-Co / C as a catalyst, injected with hydrogen, and maintained at an internal temperature. In addition, cumene hydroperoxide stream is water banung 25 weight _^0/0 concentration is by using a pressure pump and injected into the reactor top (top-down). The hydrogenation banung is cumene hydroperoxide (CHP) 150g, Pd 25 wt. _^0/0 concentration was carried out under the conditions of one of Pd-Co / C catalyst lg, hydrogen flow rate of 150 cc / min: the weight ratio of Co is 1 . In addition, the molar ratio of cumene hydroperoxide stream and injected hydrogen was maintained at 1: 8. The hydrogenation reaction time was carried out for 3 hours.

 When the hydrogenation reaction was completed, the prepared cumyl alcohol was to be supplied to the reservoir 20, which was transferred to the stripper 40. Therefore . Accordingly, the stripper 40 is filled with a mixture of cumyl alcohol obtained from the hydrogenation reaction and cumyl alcohol and cumene hydroperoxide not used in the hydrogenation reaction.

Then, the mixture was concentrated in the stripper 40, and transferred to the decomposition reaction vessel 60 through the reservoir 50, and the rest was transferred directly to the decomposition reaction vessel 60. Then, dehydration reaction is performed on the mixture using a polystyrene-based cation exchange resin (hereinafter, Resin A) having a sulfonic acid group concentration of 40% as a resin in the decomposition reaction reactor 60, cumene hydride. Loperoxide Digestion with phenol and acetone was allowed to dehydrate cumyl alcohol with alpha methyl styrene. At this time, the decomposition reaction was carried out by using a resin A 5% by weight based on 150g of the mixture. In addition, the reaction temperature was maintained at 65 ^° C. was converted until the concentration of cumene hydroperoxide is less than 1%.

The mixture of phenol, acetone and alpha methyl styrene produced in the decomposition reactor 60 was transferred to the purification apparatus 70 and the purification reaction was carried out. ^It after purification, the product was separated into each phenol, alpha-methylstyrene and acetone by distillation and transferred to a separation device 70. The Examples 7-10

 It carried out similarly to Example 6 except having changed the weight ratio of Pd: Co in Pd-Co / C catalyst. The weight ratio of Pd: Co is shown in Table 2 below.

 TABLE 2

실시예 11 내지 12

Examples 11-12

Polystyrene cation exchange resin (hereinafter, Resin B) having a concentration of 48% of sulfonic acid as a resin catalyst (Example 11), polystyrene cation exchange resin (hereinafter, Resin C) having a concentration of ⁵ % of sulfonic acid (hereinafter, Resin C) (Example 12 Was carried out in the same manner as in Example 8, except that) was used. Example 13 Resin catalyst instead was carried out in the same manner as in Example 8, except the sulfuric acid decomposition for the 150g common compound unggi half _{(60) (H 2 S0 4} ) by putting the lg that the ^"proceed to dehydration banung. Example 14

 Phenol, acetone and alpha methyl styrene were prepared according to the flowchart shown in FIG. 3.

The oxidation of cumene proceeds with an oxidant using the oxidizing half unggi 100 to prepare a stream comprising cumene hydroperoxide in 24 parts by weight _^0/0 concentration was carried out in the same manner as in Example 1.

 Thereafter, 25 wt% of the low concentration stream was separated and transferred to the reservoir 200, and then supplied to the hydrogenation reaction vessel 300.

The hydrogenation reaction reactor 300 was filled with Pd-Co / C with a catalyst, hydrogen was injected, and the reaction was performed by maintaining the internal temperature at 65 ^° C. In addition, cumene hydroperoxide stream of the reaction is 25 wt. _^0/0 concentration is by using a pressure pump was injected in half unggi the bottom (bottom-up). The hydrogenation reaction was subjected to hydrogenation reaction under conditions of 150 g of cumene hydroperoxide at a concentration of 25% by weight, Pd-Co / C catalyst lg having a weight ratio of 1: 0.2 of Pd: Co, and a hydrogen flow rate of 150 cc / min. In addition, the molar ratio of cumene hydroperoxide stream and injected hydrogen was maintained at 1: 8. The hydrogenation reaction time was carried out for 3 hours. After the hydrogenation reaction is complete, the cumyl alcohol prepared to be supplied back to the long-term (310), through which it was transferred to the first decomposition reactor (320). Resin A was fixed to the first decomposition reaction reactor 320 by a bead by means of beads to allow dehydration to alpha methyl styrene by passing through cumyl alcohol. Wherein the first decomposition half unggi 320 there was used a resin A with respect to the supplied cumyl alcohol with 5 parts by weight ⁰ /. Banung the degree was converted until held at 80 ^° C and the concentration of cumyl alkoeul less than 2% .

On the other hand, the remaining 75% stream of cumene hydroperoxide not transferred to the hydrogenation reaction reactor 300 was concentrated to 82% via stripper 400. Concentrated cumene hydroperoxide was transferred from stripper 400 to second cracking reactor 600.

 An acidic catalyst was added to the second decomposition reactor 600 to decompose cumene hydroperoxide into phenol and acetone. At this time, a sulfuric acid catalyst was added to the second cracking reactor to react the reaction. In addition, the reaction temperature was maintained at 65 ° C and switched until the concentration of cumene hydroperoxide was less than 1%.

 Phenol and acetone produced in the second decomposition reaction reactor 600 is combined with alpha methyl styrene produced in the first decomposition reaction reactor 320 through the neutralization device 700, and transferred to the separation device 800, The process of separating into phenol, acetone and alpha methyl styrene, respectively. Examples 15-16

 The same process as in Example 14 was carried out except that resin B (Example 15) and resin C (Example 16) were used as the resin catalyst. Comparative Example 1

 The oxidation of cumene using an oxidant was performed to prepare a stream including cumene hydroperoxide at a concentration of 25% by weight in the same manner as in Example 6.

Separating a portion of the cumene hydroperoxide in the prepared 25 parts by weight _^0/0 concentration was carried out with a reducing banung. At this time of lg with respect to the cumene hydroperoxide _{150g Co / Al / P0 4 (} Co:. 7 weight ⁰ /, A1: 25 parts by weight _^0/0, P: 3 parts by weight _^0/0) by using catalytic reduction with no hydrogen banung Proceed to cumil alcohol was washed. The reaction time was 3 hours.

 Upon completion of the reduction reaction, a mixture comprising cumyl alcohol prepared and cumene hydroperoxide not used in the reduction reaction was transferred to the decomposition reactor.

Sulfuric acid (¾S0 ₄ ) was added as an acidic catalyst to the decomposition reaction reactor, and the acidic catalyst was cumene by continuously dehydrating the mixture. Hydroperoxide was decomposed to phenol and acetone and cumyl alcohol was dehydrated with alpha methyl styrene. In the decomposition reaction, 4.5 wt% of sulfuric acid was added to 150 g of the mixture to carry out the reaction. In addition, the reaction temperature was maintained at 65 ^° C.

 Other conditions were carried out in the same manner as in Example 6 to prepare phenol, acetone and alpha methyl styrene. Comparative Examples 2 to 3

Of not proceed with the hydrogenation Place the cumene hydroperoxide 50g of oxide banung and 80% by weight of the huge hit enriched stripper concentration of cumene in a concentration of 27 weight _^0/0, and diluted in a solvent of acetone and 100g lg Co / Al Cumyl alcohol was prepared by reduction reaction using / P0 ₄ and Co / Zr0 ₂ catalysts. The reaction time was 3 hours.

 When the reduction reaction was completed, the reaction was carried out by transferring the reaction product to a decomposition reactor.

 Other conditions were carried out in the same manner as in Comparative Example 1 to prepare phenol, acetone and alpha methyl styrene.

 The experimental conditions of Examples 6 to 16 and Comparative Examples 1 to 3 are shown in Table 3 below.

TABLE 3

Experimental Example

 Experimental Example 1

 The conversion rate of cumene hydroperoxide (CHP), the selectivity and yield of cumyl alcohol (CA) of Examples 1 to 5 were calculated according to Equations 1 to 3 below.

The graph according to the result is shown in FIG.

 [Equation 1]

CHP conversion rate (%) = (CHP feed (wt%) - CHP product (weight _^0/0)) / (CHP feed (weight ^_0/0))

 [Equation 2]

CA selectivity (%) = (CA product (mol%) / (CHP feed (mol _^0/0) - CHP product (mol ^_0/0))

[Equation 3]-CA yield (%) = CHP conversion (%) * CA selectivity (%) Referring to Figure 4, among the Pd-Co catalyst, particularly excellent when the weight ratio of Pd: Co is 1: 0.2 It can be seen that the conversion, selectivity and yield are shown. Experimental Example 2 The conversion rate of cumene hydroperoxide (CHP), the selectivity and yield of cumyl alcohol (CA) of Examples 6 to 10 and Comparative Examples 1 to 3 were calculated according to Equations 1 to 3 of Experimental Example 1 Shown in

상기 표 4 의 결과로부터， 본 발명의 실시 예 6 내지 10 은 Pd-Co/C 를 촉매로 사용하여 수소화 반웅을 수행함으로써 , 쿠멘 하이드로퍼옥사이드 (CHP)의 전환율 및 쿠밀 알코을 (CA)의 선택도가 수소화 반웅을 진행하지 않고 촉매로 Co/Al/P0₄ 및 Co/Zr(¾ 을 사용하여 환원 반웅을 진행한 비교예 1 내지 3 보다 현저히 우수하고, 따라서 쿠밀 알코을의 생산량이 현저히 증가하였음을 알 수 있다. 실험 예 3

From the results of Table 4, Examples 6 to 10 of the present invention by performing a hydrogenation reaction using Pd-Co / C as a catalyst, the conversion rate of cumene hydroperoxide (CHP) and selectivity of cumyl alcohol (CA) It was found that the reaction was significantly better than those of Comparative Examples 1 to 3 in which reduction reaction was performed using Co / Al / P0 ₄ and Co / Zr (¾ as a catalyst without proceeding hydrogenation reaction, and thus, the yield of cumyl alcohol was significantly increased. Experimental Example 3

 Conversion rate of cumyl alcohol (CA), selectivity and yield of alpha methyl styrene (AMS) of Examples 14 to 16 and Comparative Example 1 were calculated according to Equations 4 to 6 shown in Table 5 below.

[Equation 4] CA conversion (%) = (CA feed (weight%)-

CA product (% by weight)) / (CA feed (% by weight))

Equation ⁵

AMS selectivity (%) = (AMS product (mol _^0/0) / (CA feed (mol _^0/0) - CA product (mol ^_0/0))

 [Equation 6]

 AMS yield (%) = CA conversion (%) * AMS selectivity (%)

상기 표 5 의 결과로부터， 본 발명의 실시 예 14 내지 16 은 쿠밀 알코을에서 알파 메틸 스티 렌으로의 탈수반웅을 분리하여 수행하고 레진 촉매를 사용함으로써， 비교예 1 에 비해 쿠밀 알코올 (CA)의 전환율 및 선택도가 우수하고， 최종적으로 알파 메틸 스티 렌의 생산량이 산성 촉매를 사용한 경우에 비해 현저히 증가하였음을 알 수 있다.

From the results of Table 5, Examples 14 to 16 of the present invention is carried out by separating the dehydration reaction from cumyl alcohol to alpha methyl styrene and using a resin catalyst, the conversion rate of cumyl alcohol (CA) compared to Comparative Example 1 And excellent selectivity, and finally it can be seen that the production of alpha methyl styrene was significantly increased compared with the case of using an acid catalyst.

 [Explanation of code]

 1, 10, 100: oxidation reactor

 2, 4, 20, 50, 200, 310, 500: storage

 30, 300: hydrogenation reaction

 3, 40, 400: stripper

5, 60: Decomposition van unggi ^'

 6, 70: tablet

 7, 80, 800: separation device

320: first decomposition reaction Second disassembly: neutralizer

Claims

[Patent Claims]  [Claim 11  A process for preparing cumyl alcohol in which hydrogenation of cumene hydroperoxide is carried out under a Pd-Co catalyst. ― [Claim 2]  The method of claim 1, wherein the weight ratio of Pd: Co of the Pd-Co catalyst is 1: 0.05 to 1: 1. [Claim 3]  The method of claim 2, wherein the weight ratio of Pd: Co in the Pd-Co catalyst is 1: 0.2 to 1: 0.5. [Claim 4]  The method of claim 1, wherein the Pd-Co catalyst further comprises a carrier selected from the group consisting of alumina, silica, clay, carbon, zirconia, titania, mesoporous molecular sieves and mixtures thereof. Method for preparing cumyl alcohol. [Claim 5] The method of claim 1, wherein the Pd-Co catalyst with respect to the cumene hydroperoxide to 100 parts by weight of a 25 increase _^0/0 0 concentration. Method for producing cumyl alcohol used in 5 to 15 parts by weight. [Claim 6]  (a) oxidizing cumene to produce a cumene hydroperoxide stream; (b) separating at least a portion of the cumene hydroperoxide stream and hydrogenating it under a Pd-Co catalyst to produce cumyl alcohol; (C) dewatering the reaction product comprising the cumyl alcohol; And (d) dehydrating the remaining portion of the cumene hydroperoxide stream that has not been subjected to the hydrogenation reaction to dehydrating the phenol, acetone, and alpha methyl styrene. [Claim 7]  7. The method of claim 6, wherein step (c) and step (d) are carried out simultaneously in the same reaction period of the phenol, acetone, and alpha methyl styrene. [Claim 8]  The method of claim 1, wherein steps (c) and (d) are performed separately in separate reactors. [Claim 9]  The method according to claim 6, wherein in step (c), the semicoal water containing cumyl alcohol is dehydrated under an acidic catalyst to form phenol, acetone, and alpha methyl styrene. [Claim 10]  The method according to claim 6, wherein in step (c), the semi-flour containing the cumyl alcohol is dewatered and reacted under a resin catalyst. [Claim 11]  The method for preparing phenol, acetone, and alpha methyl styrene according to claim 10, wherein the resin catalyst is a polystyrene-based cation exchange resin catalyst. [Claim 12] The method for preparing phenol, acetone, and alpha methyl styrene according to claim 10, wherein the resin catalyst is used in an amount of 1 to 10 parts by weight based on 100 parts by weight of the cumyl alcohol. [Claim 13]  The process according to claim 6, wherein the weight ratio of Pd: Co in the Pd-Co catalyst is 1: 0.05 to 1: 1. [Claim 14]  The method of claim 13, wherein the weight ratio of Pd :, Co in the Pd-Co catalyst is 1: 0.2 to 1: 0.5. [Claim 15]  The method of claim 6, wherein the Pd-Co catalyst further comprises a carrier selected from the group consisting of alumina, silica, clay, carbon, zirconia, titania, mesoporous molecular sieves and mixtures thereof. Process for preparing phenol, acetone, and alpha methyl styrene. [Claim 16]  The method of claim 6, wherein the Pd-Co catalyst is used at 0.5 to 15 parts by weight based on 100 parts by weight of cumene hadroperoxide stream at a concentration of 25% by weight. [Claim 17] 7. The method of claim 6, wherein in step (a), the cumene hydroperoxide stream is prepared at a concentration of 5 to 25 weight ⁰ / .concentrations to produce phenol, acetone, and alpha methyl styrene. [Claim 18] 7. The process according to claim 6, wherein in step (b), 5 to 50% by weight of the cumene hydroperoxide stream is separated and used for the hydrogenation reaction. [Claim 19]  The phenol, acetone, and alpha methyl styrene according to claim 6, wherein the hydrogenation reaction is performed for 0.2 to 7 hours at a hydrogen flow rate of 1: 1 to 1:10 depending on the temperature of 40 to 80 and the molar ratio to cumene hydroperoxide. Manufacturing method. [Claim 20]  The method of claim 6, wherein the selectivity of the hydrogenation reaction is 95% or more when the hydrogenation reaction is performed for 3 hours. . [Claim 21]  The method of claim 6, wherein the conversion rate of cumene hydroperoxide is 80% or more when hydrogenation reaction is performed for 3 hours. [Claim 22]  7. The method of claim 6, wherein said cumene hydroperoxide stream further comprises cumyl alcohol. [Claim 23]  7. The method of claim 6, wherein in step (b) the cumene hydroperoxide stream separates at least a portion without concentration. [Claim 24] The method for producing phenol, acetone and alpha methyl styrene according to claim 6, wherein in step (c), the reaction product containing the cumyl alcohol is concentrated and dehydrated.