Patent Description:
A process involving hydrogenation reaction by bringing a liquid organic compound into contact with hydrogen in the presence of a catalyst is conventionally known.

It is known bringing hydrogen gas into contact with a catalyst at the start-up of such a process before a liquid organic compound and hydrogen are brought into contact with a catalyst and then bringing the liquid organic compound into contact the hydrogen with the catalyst.

For example, in Patent Literature <NUM>, it is disclosed that, at the start-up of a process for hydrogenating dinitrile by bringing a liquid of aromatic dinitrile into contact with hydrogen in the presence of a catalyst, hydrogen is first brought into contact with a catalyst, follow by bringing the hydrogen and a liquid containing isophthalonitrile into contact with the catalyst. Patent Literatures <NUM> and <NUM> describe a method for producing cumene (isopropylbenzene) through hydrogenolysis of α,α-dimethyl benzyl alcohol.

As one of processes involving hydrogenation reaction by bringing a liquid organic compound into contact with hydrogen in the presence of a catalyst, there is a process for obtaining cumene, the process including subjecting liquid cumyl alcohol to (a) hydrocracking reaction, or (b) dehydration and subsequent hydrogenation reaction, in the presence of a catalyst. In the present specification, cumyl alcohol refers to <NUM>-phenyl-<NUM>-propanol.

However, when the present inventors have examined, it has been found that when the above-mentioned method is applied at the start-up of such a process, the amount of isopropylcyclohexane produced, which is a reaction by-product, increases, which is problematic.

The present invention has been made in light of the above-mentioned problem, and an object thereof is to provide a method for producing cumene wherein the amount of isopropylcyclohexane produced, which is a by-product, is small.

A method for producing cumene according to the present invention is a method for obtaining cumene by subjecting <NUM>-phenyl-<NUM>-propanol to (a) hydrocracking reaction, or (b) dehydration and subsequent hydrogenation reaction, the method comprising the following steps A and B:.

According to the present invention, there is provided a method for producing cumene wherein the amount of isopropylcyclohexane produced, which is a by-product, is small.

A method for producing cumene according to a first embodiment of the present invention will be described.

The method for producing cumene according to the first embodiment of the present invention is a method for producing cumene by subjecting <NUM>-phenyl-<NUM>-propanol to (a) hydrocracking reaction, or (b) dehydration and subsequent hydrogenation reaction, to obtain cumene. This method comprises the following steps A and B.

Step A: feeding a liquid containing cumene to a reactor loaded with a catalyst.

Step B: feeding hydrogen and a liquid containing <NUM>-phenyl-<NUM>-propanol to the reactor after the step A.

The present embodiment will be described in detail hereinafter.

In the step A, a liquid containing cumene is fed to a reactor. The concentration of cumene in the liquid in the step A can be <NUM>% by mass or more, <NUM>% by mass or more, and <NUM>% by mass or more. In one aspect, the concentration of cumene in the liquid can be <NUM>% by mass or more, and is preferably <NUM>% by mass or more, more preferably <NUM>% by mass or more, and further preferably <NUM>% by mass or more. The concentration of cumene in the liquid may be <NUM>% by mass.

The liquid may contain <NUM>-phenyl-<NUM>-propanol. In one aspect, the concentration of <NUM>-phenyl-<NUM>-propanol in the liquid can be <NUM>% by mass or less, <NUM>% by mass or less, or <NUM>% by mass or less. In one aspect, the concentration of <NUM>-phenyl-<NUM>-propanol in the liquid can be <NUM>% by mass or less, is preferably <NUM>% by mass or less, more preferably <NUM>% by mass or less, and further preferably <NUM>% by mass or less.

It is suitable to raise the temperature of the catalyst in the reactor during the step A. It is suitable to raise the temperature of the catalyst in the reactor so that the temperature is in the below-mentioned reaction temperature range at the end of the step A.

Hydrogen is not usually fed to the reactor at the start of the step A. The molar ratio of hydrogen/(cumene + <NUM>-phenyl-<NUM>-propanol) at the start of the step A is preferably <NUM>/<NUM> or less, more preferably <NUM>/<NUM> or less, and further preferably <NUM>/<NUM> or less.

In one aspect, while the step A is performed, the molar ratio of hydrogen/(cumene + <NUM>-phenyl-<NUM>-propanol) is preferably <NUM>/<NUM> or less, more preferably <NUM>/<NUM> or less, and further preferably <NUM>/<NUM> or less. In one aspect, while the step A is performed, hydrogen is not fed to the reactor.

In the step B, hydrogen and a liquid containing <NUM>-phenyl-<NUM>-propanol are fed to the reactor.

Although the concentration B <NUM> of <NUM>-phenyl-<NUM>-propanol in the liquid in the step B is not limited, it is preferable that the concentration B1 be <NUM>% by mass or more, and the concentration B <NUM> may be <NUM>% by mass or more, and although the maximum is not limited, the concentration B1 can be <NUM>% by mass or less, <NUM>% by mass or less, or <NUM>% by mass or less.

The liquid may contain cumene. In one aspect, the concentration of cumene in the liquid can be <NUM>% by mass or less, <NUM>% by mass or less, or <NUM>% by mass or less. In one aspect, the concentration of cumene in the liquid can be <NUM>% by mass or more, <NUM>% by mass or more, or <NUM>% by mass or more.

The concentration B1 of <NUM>-phenyl-<NUM>-propanol in the liquid in the step B and the concentration of <NUM>-phenyl-<NUM>-propanol in the liquid in the step A are independent. The concentration B1 of <NUM>-phenyl-<NUM>-propanol in the liquid in the step B and the concentration of <NUM>-phenyl-<NUM>-propanol in the liquid in the step A may be the same.

In the step B, it is suitable to maintain the temperature of the reactor in the below-mentioned reaction temperature range. When the temperature of the reactor is not raised in the step A, it is suitable to raise the temperature of the reactor in the below-mentioned reaction temperature range in the step B.

The amount of the liquid fed to the reactor in the step B can be suitably set according to the type and the amount of the catalyst.

In the step B, hydrogen is fed to the reactor with the liquid. The amount of hydrogen will be mentioned below.

In the step B, <NUM>-phenyl-<NUM>-propanol in the liquid containing <NUM>-phenyl-<NUM>-propanol is converted into cumene by (a) hydrocracking reaction, or (b) dehydration and subsequent hydrogenation reaction.

Then, a catalyst and conditions when <NUM>-phenyl-<NUM>-propanol is subjected to (a) hydrocracking reaction to obtain cumene will be described.

In the case of hydrocracking reaction, a liquid containing cumene is obtained by bringing hydrogen and the liquid containing <NUM>-phenyl-<NUM>-propanol into contact with the catalyst to react the <NUM>-phenyl-<NUM>-propanol and the hydrogen in the reactor.

Examples of the catalyst used in hydrocracking reaction (hereinafter occasionally described as a "hydrocracking catalyst") include catalysts containing a metal of Group <NUM>, <NUM><NUM> or <NUM> in the periodic table, and specific examples of the catalyst include catalysts containing cobalt, catalysts containing nickel, catalysts containing palladium, catalysts containing copper, and catalysts containing zinc. The catalysts containing nickel, the catalysts containing palladium, or the catalysts containing copper are preferable in view of suppressing the production of by-products. Examples of the catalysts containing nickel include nickel, nickel-alumina, nickel-silica and nickel-carbon; examples of the catalysts containing palladium include palladium-alumina, palladium-silica and palladium-carbon; and examples of the catalysts containing copper include copper, Raney copper, copper-chromium, copper-zinc, copper-chromium-zinc, copper-silica and copper-alumina.

The reactor used in hydrocracking reaction contains any one or a combination of a plurality of the above-mentioned catalysts. The reactor can be in the form of a slurry bed or a fixed bed. It is preferable to use a fixed bed in large-scale industrial operation. It is preferable to perform the reaction by a continuous method.

The amount of hydrogen consumed in hydrocracking reaction is equal to the number of moles of <NUM>-phenyl-<NUM>-propanol. However, since hydrogen-consuming components other than <NUM>-phenyl-<NUM>-propanol are also usually contained in the raw material liquid, it is suitable to feed excess hydrogen over the stoichiometric amount in view of securing the conversion rate of <NUM>-phenyl-<NUM>-propanol. As the partial pressure of hydrogen is increased, the reaction proceeds more rapidly. Therefore, the molar ratio of hydrogen/<NUM>-phenyl-<NUM>-propanol is usually adjusted to <NUM>/<NUM> to <NUM>/<NUM>, is preferably <NUM>/<NUM> to <NUM>/<NUM>, and is more preferably <NUM>/<NUM> to <NUM>/<NUM>. The molar ratio of hydrogen/(cumene + <NUM>-phenyl-<NUM>-propanol) is usually <NUM>/<NUM> or more. The molar ratio may be more than <NUM>/<NUM>.

Excess hydrogen which remains after the hydrocracking reaction can also be separated from the reaction liquid, then recycled and used. Although the hydrocracking reaction temperature is usually <NUM> to <NUM>, <NUM> to <NUM> is preferable, and <NUM> to <NUM> is more preferable. The hydrocracking reaction pressure is usually <NUM> to <NUM> kPa-G, preferably <NUM> to <NUM> kPa-G, and more preferably <NUM> to <NUM> kPa-G.

The conversion rate of <NUM>-phenyl-<NUM>-propanol when the hydrocracking reaction is applied is usually <NUM>% or more.

Catalyst and conditions when dehydration reaction followed by hydrogenation reaction are performed.

Then, a catalyst and conditions when <NUM>-phenyl-<NUM>-propanol is subjected to (b) dehydration and subsequent hydrogenation reaction to obtain cumene will be described.

In this case, <NUM>-phenyl-<NUM>-propanol in the liquid is brought into contact with a catalyst in a reactor to obtain a liquid containing α-methylstyrene by the dehydration reaction of <NUM>-phenyl-<NUM>-propanol, and then, hydrogen and the liquid containing α-methylstyrene are brought into contact with a catalyst in a reactor to allow hydrogenation reaction between the α-methylstyrene and the hydrogen to thereby obtain a liquid containing cumene.

In the present aspect, the step of dehydrating <NUM>-phenyl-<NUM>-propanol in a liquid to obtain a liquid containing α-methylstyrene may be referred to as a "dehydration step", and the step of subjecting hydrogen and the liquid containing the α-methylstyrene in the liquid to hydrogenation reaction to obtain a liquid containing cumene may be referred to as a "hydrogenation step".

Examples of the catalyst used in the dehydration step (hereinafter occasionally described as a "dehydration catalyst") include homogeneous acid catalysts such as sulfuric acid, phosphoric acid and p-toluenesulfonic acid; and solid acid catalysts such as activated alumina, titania, zirconia, silica-alumina and zeolites. It is preferable to perform the dehydration step in the presence of a solid acid catalyst, and it is more preferable to use activated alumina, in view of improving reaction efficiency.

The dehydration reaction in the dehydration step is usually performed by bringing the liquid containing <NUM>-phenyl-<NUM>-propanol into contact with the dehydration catalyst in the reactor. Since dehydration reaction is followed by hydrogenation reaction in a hydrogenation step, the liquid containing <NUM>-phenyl-<NUM>-propanol may be brought into contact with the dehydration catalyst in the presence of hydrogen. The dehydration reaction temperature is usually <NUM> to <NUM>, and preferably <NUM> to <NUM>. The dehydration reaction pressure is usually <NUM> to <NUM> kPa-G.

Examples of the catalyst used in the hydrogenation step (hereinafter occasionally referred to as a "hydrogenation catalyst") include catalysts containing a metal of Group <NUM> or <NUM> in the periodic table, and specific examples of the catalyst include catalysts containing nickel, catalysts containing palladium, catalysts containing platinum, and catalysts containing copper. The catalysts containing nickel, the catalysts containing palladium, and the catalysts containing copper are preferable from in view of suppressing the nucleus hydrogenation reaction of an aromatic ring, and high yield. As the catalysts containing nickel, nickel, nickel-alumina, nickel-silica and nickel-carbon are preferable; as the catalysts contains palladium, palladium-alumina, palladium silica and palladium-carbon are preferable; and as the catalysts containing copper, copper, Raney copper, copper-chromium, copper-zinc, copper-chromium-zinc, copper-silica and copper-alumina are preferable. These catalysts can be used alone or in combination of two or more.

The hydrogenation step is performed by bringing hydrogen and the liquid containing α-methylstyrene into contact with the hydrogenation catalyst in the reactor. Hydrogenation reaction follows the above-mentioned dehydration reaction, and some of water produced in the dehydration reaction may be separated by oil-water separation or the like, or water may be brought together with α-methylstyrene into contact with the hydrogenation catalyst without separation, in this aspect.

The amount of hydrogen consumed in the hydrogenation reaction is equal to the number of moles of α-methylstyrene. However, since hydrogen-consuming components other than α-methylstyrene are also usually contained in the raw material liquid, it is suitable to feed excess hydrogen over the stoichiometric amount in view of securing the conversion rate of α-methylstyrene. As the partial pressure of hydrogen is increased, the reaction proceeds more rapidly. Therefore, the molar ratio of hydrogen/α-methylstyrene is usually adjusted to <NUM>/<NUM> to <NUM>/<NUM>, is preferably <NUM>/<NUM> to <NUM>/<NUM>, and is more preferably <NUM>/<NUM> to <NUM>/<NUM>. Excessive hydrogen which remains after the hydrogenation reaction can also be separated from the reaction liquid, then recycled and used. The molar ratio of hydrogen/(cumene + <NUM>-phenyl-<NUM>-propanol) is usually <NUM>/<NUM> or more. In the case of the (b), the amount of substance of "hydrogen" in the molar ratio is the amount of substance of hydrogen subjected to the hydrogenation reaction, and the amount of substance of "cumene + <NUM>-phenyl-<NUM>-propanol" is the total amount of substance of cumene and <NUM>-phenyl-<NUM>-propanol in the liquid subjected to dehydration reaction. The molar ratio may be more than <NUM>/<NUM>.

Although the hydrogenation reaction temperature is usually <NUM> to <NUM>, <NUM> to <NUM> is preferable, and <NUM> to <NUM> is more preferable. The hydrogenation reaction pressure is usually <NUM> to <NUM> kPa-G.

The dehydration reaction and the subsequent hydrogenation reaction may be performed in a reactor that contains the dehydration catalyst and the hydrogenation catalyst sequentially from the upstream side in one container, a reactor that contains a catalyst obtained by physically mixing the dehydration catalyst and the hydrogenation catalyst in one container, a reactor that contains the hydrogenation catalyst supported on the dehydration catalyst in one container, or a reactor in which a container containing the dehydration catalyst and a container containing the hydrogenation catalyst are connected through a line in series sequentially from the upstream side.

The state of the contact between the catalyst and the liquid in the container can be in the form of a slurry bed or a fixed bed. It is preferable to use a fixed bed in large-scale industrial operation. In the present embodiment, the dehydration reaction and the subsequent hydrogenation reaction are performed by a continuous method.

According to a method according to the present embodiment, the amount of by-products, especially isopropylcyclohexane, in the reaction mixture can be reduced, and the selectivity from <NUM>-phenyl-<NUM>-propanol to cumene can be increased.

The above-mentioned method for producing cumene is suitably applied to a step of producing cumene in the below-mentioned method for producing propylene oxide.

Specifically, the production of propylene oxide according to an embodiment of the present invention comprises the following steps.

Oxidization step: a step of oxidizing cumene to obtain cumene hydroperoxide.

Epoxidation step: a step of reacting the cumene hydroperoxide obtained in the oxidization step and propylene to obtain propylene oxide and <NUM>-phenyl-<NUM>-propanol.

Cumene production step: a step of converting the <NUM>-phenyl-<NUM>-propanol obtained in the above-mentioned epoxidation step into cumene using the above-mentioned method for producing cumene and recycling the obtained cumene to the oxidization step.

These steps will be described hereinafter.

Cumene in the oxidization step is usually oxidized by autoxidation with oxygen-containing gas such as air and oxygen concentrated air. This oxidation reaction may be performed without using an additive, or with using an additive such as alkali. The reaction temperature is usually <NUM> to <NUM>, and the reaction pressure is usually between atmospheric pressure and <NUM> MPa.

Example of the additive include alkali metal hydroxides such as NaOH and KOH; alkaline-earth metal hydroxides; alkali metal carbonates such as Na<NUM>CO<NUM> and NaHCOs; ammonia; (NH<NUM>)<NUM>CO<NUM>; and alkali metal ammonium carbonates.

It is preferable to perform the epoxidation step in the presence of a catalyst containing titanium-containing silicon oxide in view of obtaining target propylene oxide at a high yield and a high selectivity. It is preferable that the catalyst be the so-called Ti-silica catalyst, which contains Ti chemically bound to silicon oxide. Examples of the catalyst includes catalyst in which Ti compounds are supported on silica carriers, catalysts in which Ti compounds are compounded with silicon oxide by a coprecipitation method or a sol-gel method, or zeolite compounds containing Ti.

The epoxidation reaction is performed by bringing propylene and cumene hydroperoxide into contact with a catalyst. The reaction can be performed in the liquid phase using a solvent. The solvent should be a liquid at the temperature and pressure of the reaction, and should be substantially inactive to the reactants and the products. An example of a solvent is cumene.

The epoxidation reaction temperature is generally <NUM> to <NUM>, and preferably <NUM> to <NUM>. The pressure may be a pressure enough to maintain the reaction mixture in a liquid state. It is generally advantageous that the pressure be <NUM> to <NUM> kPa.

The epoxidation reaction can be advantageously performed using a catalyst in the form of a slurry bed or a fixed bed. It is preferable to use a fixed bed in large-scale industrial operation. The epoxidation reaction can be performed by a batch method, a semi-continuous method or a continuous method.

The <NUM>-phenyl-<NUM>-propanol produced in the epoxidation reaction is fed to the above-mentioned method for producing cumene. A liquid containing <NUM>-phenyl-<NUM>-propanol after propylene oxide and unreacted propylene are collected from the reaction mixture obtained in the epoxidation reaction is usually fed to a cumene production step.

Cumene produced in the cumene production step is recycled to the oxidization step. The obtained cumene may be purified by distillation, water washing and the like before recycling to the oxidization step.

The liquid containing cumene in the step A may be any liquid as long as it is a liquid containing cumene.

The liquid containing cumene in the step A may be a liquid that has undergone the cumene production step or a liquid containing <NUM>-phenyl-<NUM>-propanol after propylene oxide and unreacted propylene are collected from the reaction mixture obtained in the epoxidation reaction. A liquid containing cumene produced in another plant may be used for the liquid containing cumene in step A. Moreover, the liquid containing cumene in the step A may be a mixture of the above-mentioned liquids containing cumene.

The liquid containing cumene in step A after passing through the above-mentioned reactor can also be circulated to the oxidization step, the epoxidation step and the cumene production step.

The liquid containing <NUM>-phenyl-<NUM>-propanol in step B may be any liquid as long as it is a liquid containing <NUM>-phenyl-<NUM>-propanol, and, for example, the liquid containing the <NUM>-phenyl-<NUM>-propanol obtained by reacting propylene with the cumene hydroperoxide obtained by oxidizing cumene can be used.

The method for producing cumene according to the present invention can be performed in (α) the case where the reaction in the cumene production step is stopped, and then resumed; or (β) the case where the cumene production step is started for the first time.

For example, in the method for producing propylene oxide, when the reaction is stopped in all the steps of the oxidization step, the epoxidation step and the cumene production step, the reaction can be started by the following methods.

In such a case, "the liquid containing cumene" fed to the reactor for the oxidization step may be the same as "the liquid containing cumene" in the step A in the above-mentioned method for producing cumene.

As an example of the method for producing cumene in such a case, a second embodiment will be described hereinafter.

A method for producing cumene according to a second embodiment is a method for producing cumene by subjecting <NUM>-phenyl-<NUM>-propanol to (a) hydrocracking reaction, or (b) dehydration and subsequent hydrogenation reaction, to obtain cumene. This method comprises the following step A' and step B'.

Step A': a step of feeding a liquid containing cumene having a <NUM>-phenyl-<NUM>-propanol concentration of <NUM>% by mass or less to a reactor loaded with a catalyst.

Step B': a step of feeding hydrogen and a liquid having a <NUM>-phenyl-<NUM>-propanol concentration of <NUM>% by mass or more to the reactor after the step A'.

In the step A', a liquid containing cumene having a <NUM>-phenyl-<NUM>-propanol concentration of <NUM>% by mass or less is fed to a reactor. It is preferable that the <NUM>-phenyl-<NUM>-propanol concentration C0 in step A' be sufficiently low, and, for example, the concentration may be <NUM>% by mass or less, <NUM>% by mass or less, <NUM>% by mass or less, <NUM>% by mass or less, <NUM>% by mass or less, or <NUM>% by mass or less, or may be substantially <NUM>.

An example of components other than <NUM>-phenyl-<NUM>-propanol in the liquid is cumene. Cumene can account for <NUM>% by mass or more of components other than <NUM>-phenyl-<NUM>-propanol in the liquid, and cumene accounts for preferably <NUM>% by mass or more, more preferably <NUM>% by mass or more, and further preferably <NUM>% by mass or more.

It is suitable that the temperature of the catalyst in the reactor be raised during the step A'. It is suitable that the temperature of the catalyst in the reactor be raised so that the temperature at the end of the step A' is in the range of reaction temperature described for the step B of the first embodiment.

After all the catalyst in the reactor is brought into contact with the liquid containing cumene having a <NUM>-phenyl-<NUM>-propanol concentration of <NUM>% by mass or less, the feeding of hydrogen to a reactor in the step A' may be started.

In the step B', hydrogen and a liquid having a <NUM>-phenyl-<NUM>-propanol concentration C1 of <NUM>% by mass or more are fed to the reactor. In the step B', the temperature of the reactor is maintained in the range of the reaction temperature described for the step B of the first embodiment. When the temperature of the reactor is not raised in the step A', the temperature of the reactor is raised in the step B' in the range of the reaction temperature described for the step B of the first embodiment.

The <NUM>-phenyl-<NUM>-propanol concentration C1 may be <NUM>% by mass or more, and the concentration C1 may be <NUM>% by mass or more. The upper limit thereof is not limited, and the concentration C1 can be <NUM>% by mass or less, <NUM>% by mass or less, and <NUM>% by mass or less.

The amount of the liquid fed to the reactor in the step B' can be suitably set according to the type and the amount of a catalyst.

Hydrogen is fed to the reactor with the liquid having a <NUM>-phenyl-<NUM>-propanol concentration of <NUM>% by mass or more, in step B'. The amount of hydrogen can be set as described for the step B of the first embodiment. Hydrogen may be started to be fed to the reactor prior to the step B', for example at the start of the step A' or in the middle of the step A', in view of improvement in the reaction rate. Alternatively, hydrogen may be started to be fed at the start of the step B' or in the middle of the step B', for example. When hydrogen is started to be fed at the start of the step A' or in the middle of the step A' and the below-mentioned step X' is provided between the step A' and the step B', the feeding of hydrogen may be continued in the step X'.

It is suitable that hydrogen be fed at least when the <NUM>-phenyl-<NUM>-propanol concentration in the liquid is <NUM>% by mass or more, in view of allowing <NUM>-phenyl-<NUM>-propanol to react efficiently.

The concentration of the <NUM>-phenyl-<NUM>-propanol in the liquid fed to the reactor may be increased rapidly from a C0 of <NUM>% by mass or less to a C1 of <NUM>% by mass or more between the A' step and the B' step. The second embodiment may include, between the step A' and the step B', a step X' of increasing the <NUM>-phenyl-<NUM>-propanol concentration in the liquid fed to the reactor from a concentration C0 of <NUM>% by mass or less to a concentration C1 of <NUM>% by mass or more gradually.

In the step X', it is suitable to maintain the temperature of the reactor in the range of the reaction temperature described for the step B of the first embodiment. When the temperature of the reactor is not raised in the step A', it is suitable to raise the temperature of the reactor in the step X' in the range of the reaction temperature described for the step B of the first embodiment.

The feeding of hydrogen to the reactor may be started in the step X'.

A metallic reactor having an inner diameter of <NUM> (the metal reactor contained a sheath having an outer diameter of <NUM> and equipped with a thermometer therein) was loaded with a catalyst (catalyst mass: <NUM>; the catalyst contained activated alumina and <NUM>% by mass palladium. A fixed bed was used for a method for supporting the catalyst.

Liquid cumene was fed to the reactor to fill the reactor with the liquid cumene under the pressure of <NUM>. Then, while nitrogen gas and liquid cumene were fed at <NUM> Nml/minute and at <NUM>/hour, respectively, to the reactor under the same pressure, the reactor was heated with an electric furnace so that the temperature of the inlet portion of the catalyst layer reached <NUM>. After the temperature of the inlet portion of the catalyst layer stabilized at <NUM>, nitrogen gas was switched to hydrogen gas, and hydrogen gas was fed at <NUM> Nml/minute under the same pressure. At almost the same time as the switch to hydrogen gas, a <NUM>-phenyl-<NUM>-propanol solution (<NUM>) (<NUM>-phenyl-<NUM>-propanol concentration: <NUM>% by mass, cumene concentration: <NUM>% by mass, isopropylcyclohexane concentration: <NUM>% by mass) was fed to the reactor at <NUM>/hour as a raw material liquid instead of liquid cumene by the switch of the liquid feeding lines. The number of moles of hydrogen fed per unit time was <NUM> times the number of moles of <NUM>-phenyl-<NUM>-propanol fed per unit time.

The amount of the liquid (reaction liquid sample) discharged from the reactor during the time from <NUM> minutes to <NUM> minutes after the start of hydrogen gas feeding was <NUM>, and the <NUM>-phenyl-<NUM>-propanol concentration in the reaction liquid was <NUM> % by mass. The analysis results are shown in Table <NUM>. The average temperature of the catalyst layer measured during collection of the reaction liquid was <NUM>. It was presumed that it was at <NUM> minutes after the start of hydrogen feeding that the <NUM>-phenyl-<NUM>-propanol concentration in the reactor became steady state.

The amount of the liquid (reaction liquid sample) discharged from the reactor during the time from <NUM> to <NUM> minutes after the start of hydrogen gas feeding was <NUM>, and when the reaction liquid was analyzed, the <NUM>-phenyl-<NUM>-propanol concentration was <NUM> % by mass. The analysis results are shown in Table <NUM>. The average temperature of the catalyst layer measured during collection of the reaction liquid was <NUM>.

The same reactor as in Example <NUM> was provided. A cumene solution (<NUM>) (cumene concentration: <NUM>% by mass, <NUM>-phenyl-<NUM>-propanol concentration: <NUM>% by mass, isopropylcyclohexane concentration: <NUM>% by mass) was fed to the reactor to fill the reactor with the cumene solution (<NUM>) under the pressure of <NUM>. Then, while nitrogen gas and the cumene solution (<NUM>) were fed at <NUM> Nml/minute and <NUM>/hour, respectively, to the reactor under the same pressure, the reactor was heated so that the temperature of the inlet portion of the catalyst layer reached <NUM>. After the temperature of the inlet portion of the catalyst layer stabilized at <NUM>, nitrogen gas was switched to hydrogen gas, and hydrogen gas was fed at <NUM> Nml/minute under the same pressure. In Example <NUM>, the raw material liquid is the cumene solution (<NUM>). The number of moles of hydrogen fed per unit time was <NUM> times the number of moles of <NUM>-phenyl-<NUM>-propanol fed per unit time.

The amount of the liquid (reaction liquid sample) discharged from the reactor during the time from <NUM> minutes to <NUM> minutes after the start of hydrogen gas feeding was <NUM>. The <NUM>-phenyl-<NUM>-propanol concentration in the reaction liquid at the time point of <NUM> minutes after the start of hydrogen gas feeding was <NUM>% by mass. The analysis results are shown in Table <NUM>. The average catalyst temperature measured after collection of the reaction liquid was <NUM>.

The same reactor as in Example <NUM> was provided. While nitrogen gas was fed to the reactor, the reactor was heated until the temperature of the inlet portion of the catalyst layer reached <NUM>, under the pressure of <NUM>. After the temperature of the inlet portion of the catalyst layer stabilized at <NUM>, nitrogen gas was switched to hydrogen gas, and hydrogen gas was fed at <NUM> Nml/minute under the same pressure. On this occasion, the temperature of the inlet portion of the catalyst layer rose to <NUM>. Then, the reactor was heated so that the temperature of the inlet portion of the catalyst layer reached <NUM> under the same pressure. Then, a <NUM>-phenyl-<NUM>-propanol solution (<NUM>) (<NUM>-phenyl-<NUM>-propanol concentration: <NUM>% by mass, cumene concentration: <NUM>% by mass, isopropylcyclohexane concentration: <NUM>% by mass) was fed to the reactor at <NUM>/hour as a raw material liquid under the same pressure. The number of moles of hydrogen fed per unit time was <NUM> times the number of moles of <NUM>-phenyl-<NUM>-propanol fed per unit time.

The reaction liquid was discharged from the reactor <NUM> minutes after the start of hydrogen gas feeding. The amount of the liquid (reaction liquid sample) discharged from the reactor during the time from <NUM> minutes to <NUM> minutes after the start of hydrogen gas feeding was <NUM>, and the <NUM>-phenyl-<NUM>-propanol concentration in the reaction liquid was <NUM>% by mass. The analysis results are shown in Table <NUM>. The average catalyst temperature measured during collection of the reaction liquid was <NUM>.

The temperature of the inlet portion of the catalyst layer is expected to rise to <NUM> under the following conditions: the same reactor as in Example <NUM> is provided; while nitrogen gas is fed to the reactor, the reactor is heated until the temperature of the inlet portion of the catalyst layer reaches <NUM>; nitrogen gas is then switched to hydrogen gas; and hydrogen gas was fed at <NUM> Nml/minute, under the pressure of <NUM>.

The <NUM>-phenyl-<NUM>-propanol conversion rate and the isopropylcyclohexane selectivity in the following Table <NUM> were calculated by the following expressions. <MAT> <MAT> <MAT> <MAT> <MAT> <MAT> <MAT> <MAT> <MAT> <MAT>.

Claim 1:
A method for producing cumene by subjecting <NUM>-phenyl-<NUM>-propanol to (a) hydrocracking reaction, or (b) dehydration and subsequent hydrogenation reaction, to obtain cumene,
the method comprising the steps of:
(A) feeding a liquid containing cumene to a reactor loaded with a catalyst; and
(B) feeding hydrogen and a liquid containing <NUM>-phenyl-<NUM>-propanol to the reactor after the step (A).