JPS6110522A - Production of aromatic trialcohol - Google Patents

Abstract

PURPOSE:To separate the titled compound in high yield from a mixture obtained by oxidizing triisopropylbenzene in an alkaline aqueous solution, separating the oil phase containing the oxidation reaction product, and reducing the water-insoluble solvent solution. CONSTITUTION:Triisopropylbenzene is oxidized with an O2-containing gas in an alkaline aqueous solution until the conversion of the isopropyl group of the triisopropylbenzene reaches >=80% to obtain an oxidation reaction mixture consisting of an oily phase containing the oxidation reaction product and an alkaline aqueous solution phase. The alkaline aqueous solution phase is separated and removed from the mixture, and the remaining oxidation reaction product is dissolved e.g. in a water-insoluble solvent to obtain the solution of the product in said water-insoluble solvent. The solution is made to contact with an aqueous solution of a sulfite under agitation to effect the reduction of the compound. The aqueous phase is removed from the resultant reduction reaction mixture consisting of two liquid phases, and the titled compound is separated from the remaining oily-phase reduction reaction mixture. USE:Modifier of polycarbonate resin, epoxy resin, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION [Technical Field of the Invention] The present invention relates to a method for producing tris(2-hydroxy-2-propyl)benzene with good yield.

[Industrial application field]

Tris(2-hydroxy-2-propyl)benzene is α,α′,α″-1-lis(hydroxyphenyl) useful as a modifier for polycarbonate resins, epoxy resins, etc.
It is a synthetic raw material for producing triisopropylbenzene.

[Prior art]

Conventionally, the method for producing tris(2-hydroxy-2-propyl)benzene is to isolate triisopropylbenzene trihydroperoxide from the oxidation reaction product of triisopropylbenzene and reduce it with sulfite (
Journal r8r praktische Ch
emie, 4 Re1he.

Band 3, 1956) is known. However, with this method, the yield when isolating triisopropylbenzene trihydroperoxide from the oxidation reaction product of triisopropylbenzene is low;
The yield of -hydroxy-2-propyl)benzene based on triisopropylbenzene is approximately 25 mo 1%.
And small. In addition, it has various drawbacks, such as the process of producing tris(2-hydroxy-2-propyl)benzene being complicated because it involves separation of triisopropylbenzene trihydroperoxide, and is therefore not a practical method for industrial production. I can't say that.

[Purpose of the invention]

The present inventors conducted studies with the aim of providing a method for producing tris(2-hydroxy-2-propyl)benzene using an industrially simple process, which is different from these conventional methods.

[Means and actions to solve the problem] As a result,
The inventors have discovered that tris(2-hydroxy-2-propyl)benzene can be produced from triisopropylbenzene in high yield and in a simple process by employing the following method, and have completed the present invention.

That is, according to the present invention, (A) triisopropylbenzene is oxidized using a molecular oxygen-containing gas in the presence of an alkaline aqueous solution until the change rate of isopropyl groups in triisopropylbenzene becomes 80% or more. (B) obtaining a two-liquid phase oxidation reaction mixture consisting of an oil phase containing an oxidation reaction product of triisopropylbenzene and an alkaline aqueous solution; (B) an alkaline aqueous solution from the two-liquid phase oxidation reaction mixture obtained in step (A) above; The triisopropylbenzene oxidation reaction product obtained by separation and removal is dissolved in a water-insoluble solvent, or a water-insoluble solvent is added to the two-liquid phase oxidation reaction mixture to dissolve the oxidation reaction product in the water-insoluble solvent. (C) obtaining a water-insoluble solvent for the oxidation reaction product by separating and removing the alkaline aqueous solution phase; (C) the water-insoluble solvent for the oxidation reaction product obtained in step (B) above, and sulfite; a step of reducing the nucleic oxidation reaction product to obtain a two-liquid phase oxidation reaction mixture by bringing two liquid phases consisting of an aqueous solution into contact with each other under stirring; (D) the two liquids obtained in step (C) above; A step of separating the phase oxidation reaction mixture to remove the aqueous phase to obtain an oil phase reduction reaction mixture, (E) separating tris(2-hydroxy-2 A method for producing an aromatic trial alcohol is provided, which comprises combining the following steps: - separating propyl)benzene.

In step (A>) of the present invention, triisopropylbenzene is oxidized.
2.3-substituted product, 1,2.4-substituted product, 1.3.5-
It may be a substituted product or a mixture of these in any proportion. Triisopropylbenzene is oxidized by a molecular oxygen-containing gas in the presence of an aqueous alkaline solution to form a two-liquid phase oxidation reaction mixture consisting of an oil phase containing oxidation reaction products and an aqueous alkaline phase. At this time, the degree of oxidation is such that the reaction rate of isopropyl groups in triisopropylbenzene is 80% or more, preferably 80% to 98%. In order to obtain an oxidation reaction product with such a high reaction rate of isopropyl groups, it is necessary to maintain the pt+ of the aqueous phase and the reaction temperature within appropriate ranges during the oxidation reaction. Specifically, these conditions vary slightly depending on the type of triisopropylbenzene, the concentration of the alkaline aqueous solution used, and other reaction conditions, but the pH of the aqueous phase is usually 8 to about 11. Preferably from about 8°C to about 10°C, and the reaction temperature is usually from about 80°C to about 120°C, preferably about 9°C.
The temperature is set at 5°C to about 110°C.

As the alkaline aqueous solution, for example, an aqueous solution of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, etc. is used, and the alkali concentration thereof is preferably 20% by weight or less.

In addition, the amount of alkaline aqueous solution used is 5 to 60% of the reaction system.
It is preferable to make it account for about % by weight.

An example of a technique for oxidizing triisopropyrhenzene until the reaction rate of isopropyl groups reaches 80% or more is described, for example, in Japanese Patent Application Laid-open No. 150529/1983. The advantage of performing such oxidation is that (C
) and bis(2-hydroperoxy-2-propyl)-2-triisopropylbenzene trihydroberoxide (hereinafter sometimes abbreviated as TRHP), which can be converted to tris(2-hydroxy-2-propyl)benzene in the step Hydroxy-2-propylbenzene (hereinafter referred to as
(sometimes abbreviated as HDHP) and bis (2-
Hydroxy-2-propyl)-2-hydroperoxy-
This oxidation reaction product, which has a higher total yield with 2-propylbenzene (hereinafter sometimes abbreviated as DHHP) than fluorine, can be processed without performing a TRHP separation operation. (By reducing Tris(2-
It is possible to obtain high yields of hydroxy-2-propyl)benzene.

The oxidation reaction mixture obtained by the oxidation reaction step is
A two-liquid phase oxidation reaction mixture is formed consisting of an oil phase containing the oxidation reaction product of triisopropylbenzene and an alkaline aqueous solution phase. Through this oxidation reaction, 1-liisopropylbenzene is oxidized to triisopropylbenzene oxidation reaction products including TRtlP, HDHP, DHHP, and the like.

The oxidation reaction product is contained in the oil phase of the oxidation reaction mixture, and the oil phase may be liquid or may exist as insoluble crystals in the alkaline aqueous solution phase. .

Since the oil phase of the oxidation reaction mixture obtained by the oxidation still contains a part of the alkaline aqueous solution, if it is directly subjected to the reduction treatment, tris(2-hydroxy-2-
It is necessary to separate the alkaline aqueous solution contained in the oxidation reaction product, since this causes problems in the separation process of propylbenzene and the like.

Therefore, in step (B) of the method of the present invention, the above (
The alkaline aqueous solution is separated and removed from the two-liquid phase oxidation reaction mixture obtained in step A) to obtain a water-insoluble solvent solution of the triisopropylbenzene oxidation reaction product. The following two methods can be adopted for this purpose.

[1] The oxidation reaction is carried out by dissolving the triisopropylbenzene oxidation reaction product obtained by separating and removing the alkaline aqueous solution from the two-liquid phase oxidation reaction mixture obtained in step (A) above in a water-insoluble solvent. Method for obtaining a water-insoluble solvent solution of the product.

[2] After adding a water-insoluble solvent to the two-liquid phase oxidation reaction mixture obtained in step (A) to dissolve the oxidation reaction product of triisopropylbenzene, by separating and removing the alkaline aqueous solution phase, A method for obtaining a water-insoluble solvent solution of the oxidation reaction product.

Among these methods, method [2] is preferred because the process is simple and the results obtained are almost the same as those obtained when method [1] is used.

Examples of water-insoluble solvents that can dissolve the oxidation reaction product of triisopropylbenzene well include pentanol, hexanol, heptatool, occunor, 2-ethylhexyl alcohol, isooctanol,
Alcohols having 5 or more carbon atoms, preferably 5 to 10 carbon atoms, such as nonanol and decanol; Ethers, ketones having 4 or more carbon atoms, preferably 4 to 8 carbon atoms, such as methane, diethyl ketone, methyl isobutyl ketone, acetophenone, benzene, toluene, xylene, cumene, cymene, triisopropylbenzene, hexane, heptane Examples include hydrocarbons or halogenated hydrocarbons such as octane, chloroborum, methylene chloride, dichloroethane, chlorobenzene, and dichlorobenzene, and two or more of these can also be used as a mixed solvent. Among these organic solvents, tris (2-hydroxy-
It is preferable to use methyl isobutyl ketone or dichloroethane, since 2-propyl)benzene can be isolated at a high yield. The amount of water-insoluble solvent used is sufficient to dissolve the oxidation reaction product,
Although it varies depending on the melting temperature, differences in raw materials, type of solvent, etc., in both methods [1] and [2], per 100 parts by weight of the oil phase of the oxidation reaction mixture,
It is preferable to use about 10 to 1000 parts by weight of the solvent.

The temperature during dissolution is arbitrary as long as the oxidation reaction mixture is completely dissolved, but 50 to 150°C is usually preferred. Furthermore, in both methods [1] and [2] above, the temperature during liquid separation of the alkaline aqueous solution is usually preferably 50 to 150°C.

When the oxidation reaction product is dissolved in a water-insoluble solvent, the above [1]
] When employing the method, the dissolved alkali aqueous solution undergoes phase separation, so it may be removed and, if necessary, washed with water. Furthermore, even when the above-mentioned method [2] is employed, the water-insoluble solvent solution of the oxidation reaction product may be washed with water if necessary after separating and removing the alkaline aqueous solution phase.

In step (C) of the method of the present invention, two liquid phases consisting of a water-insoluble solvent solution of the oxidation reaction product of triisopropylbenzene obtained in step (B) and an aqueous sulfite solution are brought into contact with each other under stirring. The oxidation reaction product is reduced by.

Examples of the sulfite that can be used in the present invention include inorganic salts of sulfite such as sodium sulfite, potassium sulfite, and ammonium sulfite, but it is advantageous to use thorium sulfite from the viewpoint of cost. Furthermore, there is no particular problem even if the sulfite contains 54% or less of carbonate or bicarbonate as an impurity. Theoretically, the amount of sulfite to be used should be equivalent to the amount of hydroperoxide groups present in the oxidation reaction product in the reaction system. It is desirable to use a slightly larger amount, and the equivalent ratio (number of moles of sulfite/g equivalent of hydroperoxide group) is usually 0.9 to 3.0, more preferably 1.
It is preferable to use it in the range of 0.05 to 1.5.

As a method for preparing a two-liquid phase solution consisting of a water-insoluble solvent solution of the oxidation reaction product of triisopropylbenzene and sulfite water/8 liquid, the following methods [1] to [4] can be considered.

[1] After adding water to the water-insoluble solvent solution, sulfite is added.

[2] After adding sulfite to the water-insoluble solvent solution,
Add water.

[3] Add the previously prepared aqueous sulfite solution to the water-insoluble solvent solution.

[4] Add the above water-insoluble solvent solution to the previously prepared aqueous sulfite solution.

Although any of these methods may be used, method [4] is preferred in the present invention from the viewpoints of reaction rate, reaction selectivity, and ease of operation. The concentration of sulfite in the aqueous phase is usually in the range of 2 to 5 Qwt%, preferably 10 to 30%.

In any of the methods [1] to [4] above, the amount of water used is usually 30 to 1000 parts by weight per 100 parts by weight of the water-insoluble solvent solution of the oxidation reaction product of triisopropylbenzene. Preferably 70 to 35
It is preferable to use 0 parts by weight.

In reducing the oxidation reaction product, any reactor to which a batch method, semi-batch method, or continuous method can be applied may be used, but in the present invention, a semi-batch method is particularly preferred.

Contacting the two-liquid phase solution when carrying out the reduction reaction of the oxidation reaction product can be carried out by a well-known stirring method. Specifically, there are stirring blade methods that rotate or vibrate stirring blades, vibration methods that move the reaction vessel itself, methods that stir by blowing out inert gas from the bottom of the reactor, and ultrasonic methods. It is possible to adopt methods such as stirring the liquid itself by making it move or flow in one direction. In this case, although it depends on the shape of the reactor used, as long as sufficient contact between the two liquid phase solutions can be achieved, any of the above-mentioned stirring methods may be used.

The reduction reaction of the oxidation reaction product is usually carried out under atmospheric pressure, but it may be carried out under reduced pressure or increased pressure as necessary (usually 100 mm 11 g to 10 g in absolute pressure).
Kg/cat, preferably 0.5 to 2 Kg/cn+
It is best to do this within the range of

The reaction temperature can usually be selected within the range from the freezing point of the water-insoluble solvent to the reflux temperature, but it is preferably carried out within the range of 50 to 150°C. The reaction time depends on the reaction temperature, etc., but the reaction time is usually in the range of 0.5 to 10 hr from the start of the reaction, so the reduction reaction of the oxidation reaction product can be carried out within this range. .

In step (D) of the method of the present invention, the two-liquid phase reduction reaction mixture obtained in step (C) is separated to remove the aqueous phase,
An oil phase reduction reaction mixture is obtained. The two-liquid phase reduction reaction mixture can be separated by a conventional oil-water separation method that utilizes the difference in specific gravity between the two liquid phases. In carrying out this liquid separation operation, the two-liquid phase reduction reaction mixture is separated from Tris (
The temperature of the two-liquid phase reduction reaction mixture is maintained at a temperature at which solid substances such as 2-hydroxy-2-propyl) benzene or sulfate do not precipitate, and the aqueous phase in which sulfate, etc. are dissolved is removed. . The temperature at this time varies somewhat depending on the type and amount of the water-insoluble solvent used, the amount of sulfite used, etc., but is preferably within the range of 50 to 150°C. The oil phase reduction reaction mixture obtained by liquid separation may be further washed with water if necessary.

In step (E) of the method of the present invention, the Urawa reduction reaction mixture obtained in step (D) is
2-propyl)benzene is separated. Specifically, a crystallization method, an extraction method, etc. can be adopted as a separation method. For example, as a crystallization method, the reduction reaction mixture is used as it is or after being concentrated, and then tris(2-hydroxy-2-propyl)benzene is crystallized. For example, how to do this.

If necessary, the tris(2-hydroxy-2-propyl)benzene thus prepared can be further recrystallized to obtain even more pure tris(2-hydroxy-2-propyl).
(propyl)benzene can be obtained.

〔Effect of the invention〕

According to the present invention, highly pure tris(2-hydroxy-2-
Propyl)benzene can be obtained in high yield.

[Embodiments of the invention]

Next, a more detailed explanation will be given with reference to examples.

Example 1 (1) In a reactor equipped with a stirrer, a sparger for air blowing, an aqueous alkali solution inlet, and a reflux condenser,
5% L3,5-triisopropylbenzene 7900
g, 800 g of 4.5% by weight Na011 aqueous solution was charged, heated to 100°C, and then heated to 5.5 kg/CI with air.
The pressure was increased to IG. After that, the air was 2.6Nn? /hr
The oxidation reaction was carried out at 100°C with stirring while blowing at a rate of .

During this time, a 4.5% by weight NaOH aqueous solution was appropriately introduced into the reactor so as to maintain the pH of the aqueous phase in the reaction solution at 8 to 10. The two-liquid phase oxidation reaction mixture containing the oxidation reaction product of L3,5-)lyisopropylhenzene, in which the reaction rate of the isopropyl group was 95% after 34.5 hours of reaction, was
00g was obtained. T RH in the oil phase of the oxidation reaction mixture
The concentrations of P, HDHP, DHHP, and tris(2-hydroxy-2-propyl)benzene were 22.2%, 38.1%, 14.0%, and 2.0% by weight, respectively.

(2) Two-liquid phase oxidation reaction mixture 15 obtained in +11 above
Add 2000g of methyl isobutyl ketone to 00g,
By separating the oil and water at a temperature of 50°C, the alkaline aqueous solution was removed and the methyl isobutyl ketone aqueous solution 33 containing the 1.3.5-triisopropylbenzene oxidation reaction product was obtained.
00g was obtained. The concentrations of TRHP, DHHP, and tris(2-hydroxy-2-propyl)benzene in the solution were 8.2% by weight, 14.1% by weight, 5.2% by weight, and 0.74% by weight, respectively. 1゜3.5-1-
TRIIP for lyisopropylbenzene (pure product)
, HDHP, DHHP and tris(2-hydroxy-
Combined with 2-prozyl)benzene, the yield is 76.6 mol%.
Met.

(3) 1,638 g of a 19% by weight sulfite aqueous solution was charged into 31 reaction vessels equipped with a reflux condenser and a stirring device, and the 1,3.5-triisopropylbenzene obtained in (2) above was oxidized with this while stirring. 700 g of reaction product-methyl isobutyl ketone solution was added over 1.5 hours (Na2
The equivalent ratio of SOa/hydroperoxide is 1.5).

During this time, the reaction temperature was maintained at reflux temperature (90-92°C). After the addition was completed, stirring was continued at reflux temperature for 60 minutes to obtain a two-liquid phase oxidation reaction mixture. The mixture was then cooled to 86°C for 10
It was left standing for a minute. Excluding the separated aqueous phase, 25.0ii1
% of tris(2-hydroxy-2-propyl)benzene was obtained. The yield of tris(2-hydroxy-2-propyl)benzene was 97 mo1% based on the charged TRHP, HDHP, DHHP, and tris(2-hydroxy-2-propyl)benzene.

(4) Tris(2-hydroxy-
As a result of cooling 680 g of a solution of 2-propyl)benzene in methyl isobutyl ketone to room temperature and filtering out the precipitated crystals, 155 g of white crystals of tris(2-hydroquine-2-propyl)benzene with a purity of 96.0% were obtained. Ta. 1,
3.5-) Tris(2) from lysobrobylbenzene
-Hydroxy-2-propyl)benzene yield is 65m
o1%.

Example 2 (J,) 61,201 g of 19% by weight thorium sulfite aqueous solution was charged into the reaction tank shown in (3) of Example 1, and L3 obtained in (2) of Example 1 was added to this while stirring. ,5-
700 g of methyl isobutyl ketone solution containing the oxidation reaction product of triisopropylbenzene was added over 2 hours (NazSO3/hydroperoxide, equivalent ratio 1.1).
).

During this time, the reaction temperature was maintained at reflux temperature. After addition, 2
After continuing to stir at reflux temperature for an hour, the two-liquid phase reduction reaction mixture was cooled to 87° C. and allowed to stand for 10 minutes. Excluding the separated aqueous phase, 24.6% by weight of Tris(2-hydroxy-2-
691 g of a methyl isobutyl ketone solution containing (propyl)benzene was obtained. Preparation TRHP, HDHP, D
HHP and tris(2-hydroxy-2-propyl)
The yield of tris(2-hydroxy-2-propyl)benzene based on benzene was 97 mo1%.

(2) Tris(2-hydroxy-
691 g of a solution of methyl isobutyl ketone (2-propyl)benzene was cooled to room temperature, and the precipitated crystals were filtered and dried. As a result, tris(2-hydroxy-
152 g of white crystals of 2-propyl)benzene were obtained.

1.3.5- The yield of tris(2-hydroxy-2-propyl)benzene from triisopropylbenzene is 6
It was 3.6 mo1%.

Example 3 (1) To 1500 g of the two-liquid phase oxidation reaction mixture containing the oxidation reaction product of 1,3.5-)lyisopropylbenzene obtained in (1) of Example 1, 1,2-dichloroethane 4 was added.
200 g was added, and the aqueous alkali solution was removed by oil-water separation at a temperature of 60° C. to obtain 5500 g of a 1.2-dichloroethane solution containing an oxidation reaction product of 1.3.5-1-lyisopropylbenzene. TRHP in the solution,
HD I-I P, D II HP and Tris (
The concentrations of 2-hi)'roxy-2-propyl)benzene are 4.92% by weight, 8.46% by weight, and 3.11% by weight, respectively.
and 0.44% by weight.

(2) Into the reduction reaction tank shown in (3) of Example 1, 1400 g of a 14-fold reserved sodium sulfite aqueous solution was charged, and while stirring, the 1,3.5-triisopropyl obtained in the above (1) was added. 1000 g of a 1,2-dichloroethane solution containing the benzene oxidation reaction product was added over 2 hours (Na
2SO2/hydroperoxide equivalent ratio is 1.1). During this time, the reaction temperature was maintained at reflux temperature (75-77°C). After the addition was completed, stirring was continued at reflux temperature for 2 hours, and then the two-liquid phase oxidation reaction mixture was cooled to 70° C. and allowed to stand for 10 minutes.

Excluding the separated aqueous phase, 14.9% by weight of Tris(2-
hydroxy-2-propyl)benzene
The yield of tris(2-hydroxy-2-propyl)benzene based on propyl)benzene was 97 mo1%.

(3) 980 g of the 1,2-dichloroethane solution containing tris(2-hydroxy-2-propyl)benzene obtained in (2) above was cooled to 20°C, and the precipitated crystals were filtered and dried. 128 g of white crystals of tris(2-hydroxy-2-propyl)benzene with a purity of 94.6% were obtained. The yield of benzene was 61.6 mo1%.

Example 4 (1) To 1500 g of the two-liquid phase oxidation reaction mixture containing the oxidation reaction product of 1.3.5-triisopropylbenzene obtained in (11) of Example 1, ■-octatool/toluene mixed solvent was added. (l-octanol/Toluev weight ratio, 2
18) Add 4500g and remove the alkaline aqueous solution by separating oil and water at a temperature of 70°C.
-1 containing 1-lyisobrobylbenzene oxidation reaction product
- 5800 g of octanol/toluene solution were obtained.

The concentrations of TRHP, HDHP, DHHP, and tris(2-hydroxy-2-propyl)benzene in the solution were 4.67% by weight, 8.02% by weight, and 2.95% by weight, respectively.
and 0.42% by weight.

(2) Into the reduction reaction tank shown in (3) of Example 1, 1154 g of a 19% by weight sodium sulfite aqueous solution was charged, and while stirring, the 1,3.5-)liisopropylene obtained in (1) above was added. A 1-octatool/toluene solution containing the virhenzene oxidation reaction product was added over 1.5 hours (Na
1503/hydroperoxide equivalent ratio 1.3). The reactor reaction temperature was kept at reflux temperature (88-90°C). After the addition was completed, stirring was continued at reflux temperature for 60 minutes, and then the two-liquid phase reduction reaction mixture was cooled to 85° C. and allowed to stand for 10 minutes.

Excluding the separated aqueous phase, 14.1% by weight of Tris(2-
991 g of a 1-octatool/toluene solution containing hydroxy-2-propyl)benzene was obtained.

The yield of tris(2-hydroxy-2-propyl)benzene was 98 mo 1% based on the charged TRt[P, HDHP, DHHP and tris(2-hydroxy-2-propyl)benzene.

(3) 1-octatool/containing tris(2-hydroxy-2-propyl)benzene subjected to f4F in (2) above
After cooling 991 g of toluene solution to 20°C, the precipitated crystals were separated by filtration and dried. As a result, Tris (2-
White crystals of hydro+cy(2-propyl)benzene93.
6g was obtained.

1.3.5-) The yield of tris(2-hydroxy-2-propyl)benzene from lysopropylhenzene is 4
It was 8.4 mo1%.

Claims (1)

[Claims] (1) (A) By oxidizing triisopropylbenzene using a molecular oxygen-containing gas in the presence of an alkaline aqueous solution until the change rate of the isopropyl group in triisopropylbenzene becomes 80% or more, triisopropylbenzene is produced. a step of obtaining a two-liquid phase oxidation reaction mixture consisting of an oil phase containing an oxidation reaction product and an alkaline aqueous solution phase; (B) separating and removing the alkaline aqueous solution phase from the two-liquid phase oxidation reaction mixture obtained in step (A) above; The resulting triisopropylbenzene oxidation product is dissolved in a water-insoluble solvent, or a water-insoluble solvent is added to the two-liquid phase oxidation reaction mixture to dissolve the oxidation reaction product in the water-insoluble solvent, and then an alkali a step of obtaining a water-insoluble solvent solution of the oxidation reaction product by separating and removing the aqueous solution phase; A step of reducing the oxidation reaction product to obtain a two-liquid phase oxidation reaction mixture by bringing two liquid phases consisting of a step of separating the reaction mixture to remove the aqueous phase to obtain an oil phase reduction reaction mixture; (E) separating tris(2-hydroxy-2-propyl) from the oil phase reduction reaction mixture obtained in step (D) above; ) A method for producing an aromatic trial alcohol, which consists of the step of separating benzene, and the combination of the following steps.