JP2002226406A - Method for producing 1,3,5-trimethylbenzene - Google Patents

Abstract

PROBLEM TO BE SOLVED: To produce 1,3,5-trimethylbenzene from a mixture of trimethylbenzene isomers containing ethyltoluene. SOLUTION: 1,3,5-Trimethylbenzene is produced from a mixture of trimethylbenzene isomers containing ethyltoluene in high efficiency by a step to perform at least one of deethylation reaction, hydrogenative deethylation reaction and transalkylation reaction of ethyltoluene and the isomerization reaction of trimethylbenzene and a step to separate the 1,3,5-trimethylbenzene by adsorption.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a process for preparing 1,3,5-isomeric trimethylbenzene containing ethyl toluene.
Trimethylbenzene (hereinafter abbreviated as "1,3,5-TMB") is converted into at least one of ethyl toluene dehydrogenation reaction, hydrodeethylation reaction, transalkylation reaction and isomerization reaction of trimethylbenzene. The present invention relates to a method for producing from a step of performing and a step of adsorbing and separating 1,3,5-trimethylbenzene. 1,3,5-TM
B oxidizes the methyl group and is important as a raw material for agricultural chemicals, resins and the like.

[0002]

BACKGROUND OF THE INVENTION 1, 3, 5-TMB are distilled or from coal tar neutral oil is produced by the presence methylation of specific catalysts of the meta xylene HF-BF _3. However, since the production method is special, there are problems that a large distillation cost is required, and that the use of a special catalyst results in extremely high equipment costs such as measures against corrosion.

[0003]

1,3,5-TMB is present in C9 or higher aromatic oils obtained by removing benzene, toluene and xylene from aromatic oils in petroleum refining and petrochemicals. Therefore, from the C9 aromatic oil component, 1,3,3
If it is possible to separate 5-TMB, 1,3,5-TMB at low cost
Can be manufactured. However, C9 component aromatic oil contains T
A large amount of ethyl toluene (hereinafter abbreviated as “ET”) is present in addition to MB. ET has three types of isomers like TMB and has a boiling point very close to that of TMB, so that it is extremely difficult to separate 1,3,5-TMB by distillation. The present invention aims to solve such a problem.

[0004]

The C9 aromatic fraction produced in petroleum refining and petrochemicals contains ET and propylbenzene in addition to TMB. Table 1 shows the boiling points and melting points of these aromatic components.

[0005]

[Table 1]

In particular, the boiling points of TMB and ET are very similar, and 1,3,5-TMB has almost the same boiling point as 2-ET. Therefore, it is impossible to separate 1,3,5-TMB by the distillation method. On the other hand, the melting point is 1,3,5-T
MB and 1,2,4-TMB are almost the same, and it is impossible to separate 1,3,5-TMB by the cryogenic separation method.

The inventors of the present invention have conducted intensive studies to solve the above-mentioned problems.
By performing at least one of a hydrodeethylation reaction and a transalkylation reaction, the compound is converted into a compound which can be easily separated by distillation from TMB, and 1,2,4
-1,3,5-TMB is continuously formed by combining the step of isomerizing 1,2,3-TMB into 1,3,5-TMB and the step of adsorbing and separating 1,3,5-TMB. It has been found that it is possible to efficiently and efficiently manufacture.

That is, the present invention relates to a method for preparing 1,3,5-trimethylbenzene isomer mixture containing ethyltoluene.
In producing trimethylbenzene, (1) a step of performing at least one reaction of deethylation, hydrodeethylation, and transalkylation of ethyltoluene, and isomerization of trimethylbenzene; and (2)
A step of adsorbing and separating 1,3,5-trimethylbenzene,
A method for producing 1,3,5-trimethylbenzene, comprising: ".

[0009]

DESCRIPTION OF THE PREFERRED EMBODIMENTS After 1,3,5-TMB is adsorbed and separated from a C9 aromatic oil containing ET and TMB, the remaining 1,2,4- and 1,2,3-TMB are separated by 1,3. , 5-T
In the process of isomerizing into MB and adsorbing and separating 1,3,5-TMB again, it is necessary to separate and / or remove components other than TMB from the C9 aromatic oil. However, among the C9 aromatic components, especially ET has a boiling point very close to that of TMB, so that it cannot be substantially separated and removed by the distillation method.

[0010] In order to solve this problem, if ET can be converted into a component which can be easily removed by TMB and distillation by reaction, it can be removed. From such a viewpoint, as a result of intensive studies, ET is dealkylated and / or hydrodealkylated and converted to toluene, or ET is transalkylated with another ET or another compound,
Mainly, by converting to toluene and a C10 aromatic component, it can be easily separated by distillation from TMB.

[0011] Such a reaction is possible by contacting a C9 aromatic oil with an acid type catalyst. As the acid type catalyst,
Examples thereof include a solid acid catalyst such as a silica-alumina catalyst, a solid phosphoric acid catalyst and an acid type zeolite catalyst, and a Friedel-Crafts catalyst such as aluminum chloride, and any catalyst can be used. And among the solid acid catalysts, more preferred are acid-type zeolite catalysts. As the zeolite that can be used as the acid type zeolite catalyst, any zeolite having a pore diameter capable of adsorbing ET can be used. By way of example, ZSM known as MFI-type zeolite
-5, pentasil-type zeolite, mordenite-type zeolite, faujasite-type zeolite, and the like. More preferably, 1,2,4- and / or 1,2,3-TMB can be isomerized to 1,3,5-TMB simultaneously with the ET conversion reaction. Zeolites satisfying such requirements include mordenite-type zeolites and faujasite-type zeolites. In particular, a mordenite zeolite is more preferably used.

The mordenite-type zeolite exists in nature, and natural zeolites can be used. However, synthetic products having a high zeolite content and containing few impurities are more preferable. Since the synthetic zeolite is generally a powder, it is preferable that the zeolite be molded before use. Examples of the molding method include a compression molding method, a rolling method, and an extrusion method, and the extrusion method is more preferable. In the extrusion method,
Binders such as alumina sol, alumina gel, bentonite and kaolin and, if necessary, a surfactant such as sodium dodecylbenzenesulfonate, span and rheodol are added to the synthetic zeolite powder as a molding aid and kneaded. If necessary, a machine such as a kneader is used. Furthermore, depending on the metal added to the catalyst, a metal oxide such as alumina or titania is added at the time of zeolite molding to increase the amount of the metal added to the catalyst or to improve the dispersibility. The kneaded mixture is extruded from the screen. Industrially, for example, an extruder called an extruder is used. The kneaded material extruded from the screen becomes a noodle-like material. The size of the compact is determined by the screen diameter used. The screen diameter is preferably 0.
A diameter of 2 to 1.5 mm is used. It is preferable that the noodle-shaped molded body extruded from the screen is treated by a marmellaizer in order to round corners. The formed body thus formed is dried at 50 to 250 ° C.
After drying, 250-600 to improve the molding strength
C., preferably 350-600.degree.

[0013] The molded article thus prepared is a solid.
An ion exchange treatment for imparting acidity is performed. solid
As a method of imparting acidity, ammonium ions are contained.
(Eg, NH_FourCl, NH_FourNO_Three, (NH_Four)
_TwoSO_FourEtc.) and ion exchange of zeolite
Exchange site with NH_FourIntroduce ions, then dry and bake
By conversion to hydrogen ions, or directly
Compounds containing acids (eg, HCl, HNO_Three, H_ThreeP
O_Four, H_TwoSO_FourEtc.), zeolite ion exchange site
There is a method to introduce hydrogen ions into
The former is preferred, as it may destroy the site structure.
That is, ion exchange treatment is performed with a compound containing ammonium ions.
Is managed. Alternatively, divalent and trivalent metal ions are converted to zeolite
Zeolite can also be introduced into ion exchange sites
Can be given solid acidity. With divalent metal ions
And the alkaline earth metal ion Mg²⁺, C
a²⁺, Sr ²⁺, Ba²⁺Can be cited as an example.
The trivalent metal ion is a rare earth metal ion Ce
³⁺, La³⁺Can be cited as an example. Divalent and
And / or a method for introducing a trivalent metal ion and an ammonium ion
Combines the method of introducing hydrogen ions on or directly
It can be used in some cases, and sometimes it is more preferable. I
The on-exchange treatment is usually an aqueous solution, using a batch method or a distribution method.
Done. The processing temperature is from room temperature to 100 ° C.
Is normal. The ion exchange treatment was performed in this way.
Thereafter, if necessary, a hydrogenation active metal is supported. Special
In addition, when hydrodealkylating ET, hydrogenation activated gold
It is preferred to carry a genus. As hydrogenation active metal
Is preferably rhenium, platinum, nickel, palladium, etc.
Commonly used. The preferred loading varies depending on the metal to be loaded.
Needless to say. For example, in the case of rhenium
The preferred loading amount is 0.01 to 1.0 weight based on the whole catalyst.
%, More preferably 0.05 to 0.5% by weight.
is there. In the case of platinum, it is 1 to 1000 ppm,
Preferably it is 10 to 500 ppm. In the case of platinum
When the supported amount increases, depending on the reaction conditions, the aromatic ring
Is not preferred because nuclear hydrogenation occurs. Nickel, para
In the case of indium, 0.05 to 0.5% by weight is preferably used.
Can be. The catalyst prepared in this way is 50 to 2
Dried at 50 ° C for 30 minutes or more, before use
It is baked at -600 ° C for 30 minutes or more.

The C9 aromatic oil is preferably brought into contact with the catalyst in a gaseous or liquid phase. At this time, the reaction is preferably performed in the presence of hydrogen. More preferably, the contact is performed under gas-phase flow reaction conditions. The contact between the C9 aromatic oil and the catalyst is W / F
H / g-mol in the range of 5 to 250 g-cat. H / g-mol (W is the catalyst weight (g-cat.)
Is the amount of C9 aromatic oil supplied to the reaction per hour (g
-mol / h)). The reaction temperature is 200 to 450 ° C, preferably 250 to 400 ° C, and the reaction pressure is 0.1 to
It is 10 MPa, preferably 0.1 to 5 MPa. Hydrogen feed is expressed by a H ₂ / F, 0.1~20mol / m
ol, preferably 1 to 10 mol / mol. Under such reaction conditions, the ethyltoluene in the C9 aromatic oil is
At least one of a dealkylation reaction, a hydrodealkylation reaction and a transalkylation reaction occurs, and ET
At least partly decreases. On the other hand, the 1,3,5-isomer having less than the equilibrium concentration is 1,2,4- and / or
Increased by 3-isomerization reaction. In this way,
As shown in FIG. 1, the reacted C9 aromatic oil is supplied to the adsorption separation step via a distillation tower for removing low-boiling substances and a distillation tower for removing high-boiling substances.

The adsorbent used in the adsorption separation step is preferably a zeolite adsorbent. As the zeolite, faujasite-type zeolite is preferable, and a synthetic product is more preferably used because of its high zeolite content. X-type and Y-type exist in the synthetic faujasite-type zeolite. Either zeolite can be used, but Y-type zeolite is particularly preferable. Since the synthetic zeolite is generally a powder, it is preferable that the zeolite be molded before use. Examples of the molding method include a compression molding method, a rolling method, and an extrusion method, and the extrusion method is more preferable. In the extrusion method, alumina sol is added to the synthetic zeolite powder,
Binders such as alumina gel, bentonite and kaolin and, if necessary, surfactants such as sodium dodecylbenzenesulfonate, span and rheodol are added as a molding aid and kneaded. If necessary, a machine such as a kneader is used. The kneaded mixture is extruded from the screen. Industrially, for example, an extruder called an extruder is used. The kneaded material extruded from the screen becomes a noodle-like material. The size of the compact is determined by the screen diameter used. The screen diameter is preferably 0.
A diameter of 2 to 1.5 mm is used. It is preferable that the noodle-shaped molded body extruded from the screen is treated by a marmellaizer in order to round corners. The formed body thus formed is dried at 50 to 250 ° C.
After drying, 250-600 to improve the molding strength
C., preferably 350-600.degree.

The calcined adsorbent is subjected to an ion exchange treatment with a preferred metal ion. Here, an adsorbent containing potassium ions at the ion exchange site is preferable. The potassium ions are introduced by an ion exchange treatment with an aqueous solution containing K ⁺ -containing hydrochloride, nitrate, carbonate, hydroxide or the like by a batch method or a flow method. It is preferable that the adsorbent contains silver ions and lead ions in addition to potassium ions, since the adsorption / separation performance is further improved. Such an ion exchange treatment may be performed at the stage of the zeolite powder and molded, or may be performed after the molding.

The adsorbent removes water of crystallization in the zeolite before use. Usually, by heating at 200 to 600 ° C., most of the crystallization water can be removed.

The present adsorbent is used to convert C9 aromatic oil into 1,
Adsorption separation technology for adsorbing and separating 3,5-TMB is as follows:
A so-called chromatographic preparative method may be used, or an adsorptive separation method using a simulated moving bed may be used. Separation by a simulated moving bed is most preferably used when a specific isomer is separated and produced.

The continuous adsorption / separation technique using a simulated moving bed is performed by continuously circulating the following adsorption operation, concentration operation, desorption operation and desorbent recovery operation as basic operations. (1) Adsorption operation: The raw material feed containing the mixture of aromatic isomers comes into contact with the adsorbent of the present invention, and the component having a higher adsorption power is selectively adsorbed. The strongly adsorbed component is recovered together with a desorbing agent described later as an extract component. (2) Concentration operation: The weakly adsorbed component is further brought into contact with the adsorbent, and the component with weaker adsorbing power is more purified, and is recovered from the raffinate together with the desorbent. (3) Desorption operation: The highly purified weakly adsorbed component is recovered as raffinate, while the strongly adsorbed component is expelled from the adsorbent by the desorbent and recovered as an extract component with the desorbent. . (4) Desorbent recovery operation: The adsorbent having substantially adsorbed only the desorbent is brought into contact with a part of the raffinate stream, and a part of the desorbent contained in the adsorbent is recovered as a desorbent recovery stream. .

FIG. 2 schematically shows the adsorption separation operation using the simulated moving bed. Adsorption chambers 1 to 12 filled with the adsorbent are continuously circulated and connected.

The desorbing agent preferably used in the present invention is selected in consideration of the desorbing power, the difference in boiling point from the substance to be separated, and the like.
In the present invention, toluene, xylene and ethylbenzene are particularly preferably used. In the case of xylene, any isomer may be used, but para-xylene is particularly preferred.

Further, the coexistence of these toluene, xylene and ethylbenzene improves the adsorption / separation performance.

Hereinafter, an embodiment will be described.

[0024]

Example 1 (Preparation of catalyst) 74.2 g of powder of Na-type synthetic mordenite (SiO ₂ / Al ₂ O ₃ = 18.6 mol / mol, mordenite content 94.3 wt%) manufactured by Tosoh Corporation 39.5 g of alumina powder (Al ₂ O ₃ content: 76.1 wt%, SCF type, Condea) having a boehmite structure (α-alumina monohydrate), alumina sol (Al ₂ O ₃ content: 10 wt%, colloidal alumina) 200, Nissan Kagaku) 80 grams, alumina gel powder (Al ₂ O ₃ content 70)
10% by weight, Catalid AP (C-10), 10 g of distilled water and 10 g of distilled water were mixed for about 1 hour to obtain a paste-like mixture. This was formed into a noodle shape through a screen having a hole of 0.8 mmφ. Thereafter, it was dried at 120 ° C. overnight. 12-32 after drying
The particles were classified with a mesh sieve. After that, at 500 ° C. for 2 hours,
It was fired in an air atmosphere to obtain a Na-type mordenite compact. 50 g of the molded body was mixed with 250 ml of an aqueous solution containing 5 wt% of calcium nitrate (Katayama Chemical Co., Ltd.) at 80 ° C. and 30
The ion exchange treatment was performed for minutes. After that, 250m of distilled water
After washing once with l, the ion exchange treatment with an aqueous solution of calcium nitrate and the washing with distilled water were repeated a total of five times. Thereafter, the operation of washing with 250 ml of distilled water at 80 ° C. for 30 minutes was repeated five times. Next, ammonium ion exchange treatment was performed at 80 ° C. for 30 minutes using a solution of 5 g of ammonium chloride (Katayama Chemical Co., Ltd.) dissolved in 250 ml of distilled water. Thereafter, an operation of washing with 250 ml of distilled water at 80 ° C. for 30 minutes was performed five times. Next, rhenium oxide (VI
I) A mordenite molded body subjected to ammonium ion exchange was immersed in a solution obtained by dissolving 0.13 g of (Re ₂ O ₇ ) (Katayama Chemical Co., Ltd.) in 75 g of distilled water, and allowed to stand at room temperature for 4 hours. Occasional stirring was performed. The solution was drained by decantation and dried at 120 ° C. overnight. The ion exchange rate of the catalyst thus prepared was measured by the Kjeldahl method for NH ₄ ions and by the atomic absorption method for Na and Ca. Among the mordenite ion exchange sites, NH ₄ , Ca, and Na ions were 42, 46, and 12 equivalent%, respectively. On the other hand, Re
Was analyzed by a fluorescent X-ray method. As a result, the supported amount of Re was 0.16% by weight on a dry basis. Prior to use, the catalyst thus prepared was calcined at 540 ° C. for 2 hours to convert NH ₄ ions to H ions, and converted to the acid form. This catalyst is referred to as “catalyst 1”.

(Catalyst Reaction) 15 g of Catalyst 1 was charged into a reaction tube, and the reactivity of C9 aromatic oil was subjected to a fixed bed flow gas phase reaction in the presence of hydrogen. The reaction conditions are as follows.

Reaction temperature 320 ° C. Reaction pressure 1.0 MPa W / F 35 g-cat.h / g-mol H ₂ / F 5 mol / mol The results of the feed and the liquid phase in the reaction product are shown in Table 2. It was shown to.

[0027]

[Table 2]

From Table 2, it is apparent that the ET concentration decreases due to the reaction and the 1,3,5-TMB concentration increases due to the isomerization reaction.

Example 2 A catalyst was prepared in the same manner as in Catalyst 1, except that chloroplatinic acid was used instead of rhenium oxide to carry 25 ppm of Pt on the catalyst. This catalyst is referred to as “catalyst 2”.

15 grams of Catalyst 2 was charged into a reaction tube, and a C9 aromatic oil was reacted in the presence of hydrogen in a fixed bed flow gas phase reaction. The reaction conditions are as follows.

Reaction temperature 320 ° C. Reaction pressure 1.0 MPa W / F 35 g-cat. · H / g-mol H ₂ / F 2 mol / mol The results of the feed and the liquid phase in the reaction product are shown in Table 2. It was shown to.

Examples 3 to 7 and Comparative Example 1 (Definition of Adsorption Selectivity) In the batch evaluation in Examples, the adsorption performance of the adsorbent is represented by the adsorption selectivity (α) of the equation (1).

[0033]

(Equation 1)

Here, A and B indicate one of the components, and S
Represents an adsorption phase, and L represents a liquid phase in equilibrium with the adsorption phase.

When the value of the adsorption selectivity (α _{A / B} ) is larger than 1, the component A is selectively adsorbed, and when smaller than 1, the component B is selectively adsorbed. Further, the adsorbent having the value of the adsorption selectivity (α) larger than 1 or the adsorbent smaller than 1 and close to 0 facilitates the adsorption and separation of A and B.
When α _{A / B} is close to 1, the components A and B cannot be separated. When A is a desorbing agent (hereinafter abbreviated as "Des") and B is a component showing the maximum adsorption strength in the feed material components, the value of α _{A / B} is preferably as close to 1 as possible. When it is extremely large, the adsorbed components cannot be sufficiently desorbed. On the other hand, when it is significantly smaller than 1, the desorbent is strongly adsorbed by the adsorbent, and the next component to be adsorbed cannot be sufficiently adsorbed.

(Preparation of adsorbent) Sodium type Y-type zeolite (hereinafter referred to as Na-Y) (manufactured by Tosoh Corporation)
Zeolum Na-5.5Y powder product) 100 parts by weight of alumina sol (Nissan Chemical No. 200; Al ₂ O) as a binder
₃ = 10 wt%) and kneaded by adding 15 parts by weight in terms of alumina. The kneaded material was extruded from a screen having a hole of 0.4 mmφ, and was formed into a noodle shape. After drying the formed NaY-type zeolite at 120 ° C, 500
Fired at ℃. This adsorbent is abbreviated as adsorbent 1.

Adsorbent 1 as a NaY-type zeolite compact
Of 10 g of potassium nitrate (Katayama Chemical Co., Ltd.) at 80 ° C. and 30 ml
Ion exchange for minutes. Then, it was washed with 50 ml of distilled water. Again, the same ion exchange treatment with potassium nitrate aqueous solution and washing with distilled water were repeated 5 times in total. Thereafter, the plate was washed with 50 ml of distilled water at 80 ° C. for 30 minutes. This water washing operation was repeated five times to prepare a KY type zeolite adsorbent (hereinafter abbreviated as “adsorbent 2”).

1.8 g of silver nitrate (Katayama Chemical Co., Ltd.) (equivalent to about 30 equivalent% of Ag ions with respect to the KY type adsorbent) was prepared from KY type zeolite prepared in the same manner as in adsorbent 2. It was immersed in 50 ml of a dissolved aqueous solution and subjected to silver ion exchange at 80 ° C. for 30 minutes. Then, add 50 ml of distilled water
Washed with water at 0 ° C. for 30 minutes. This washing operation was repeated five times to prepare an Ag-KY type zeolite adsorbent (hereinafter abbreviated as "adsorbent 3").

2.33 g of lead nitrate (Katayama Chemical Co., Ltd.) was prepared from KY type zeolite prepared in the same manner as in adsorbent 2 (corresponding to about 40 equivalent% of Pb ion to KY type adsorbent). Was dissolved in 50 ml of an aqueous solution in which was dissolved, and lead ion exchange was performed at 80 ° C. for 30 minutes. Then, add 50 ml of distilled water
Washed with water at 0 ° C. for 30 minutes. This water washing operation was repeated five times to prepare a Pb-KY type zeolite adsorbent (hereinafter abbreviated as “adsorbent 4”).

Immediately before the evaluation of the adsorption separation performance,
It was baked at 00 ° C. for 30 minutes.

(Measurement of Adsorption Selectivity) An autoclave having an internal volume of 5 ml was charged with 2 g of the adsorbent and 3 g of the raw material, and
The mixture was left at 30 ° C. for 30 minutes with occasional stirring. The adsorption feed material liquid and the liquid phase after the adsorption experiment were analyzed using a gas chromatograph. Using the analysis result, the adsorption selectivity was calculated according to the equation (1). The feedstock liquid composition (weight ratio) used was as follows. n-Nonane was used as an internal standard not adsorbed on the adsorbent.

N-nonane: 1,3,5-TMB: 1,2,4-TMB: 1,2,
3-TMB: 2-ET: 3-ET: 4-ET: Des = 5: 5: 15: 5:
5: 10: 5: 50 Paraxylene, toluene and ethylbenzene were evaluated as desorbing agents. Table 3 shows the results.

[0043]

[Table 3]

As is apparent from Table 3, KY, Ag
By using -KY, Pb-KY adsorbent and desorbent para-xylene, toluene, and ethylbenzene,
It can be seen that 1,3,5-trimethylbenzene can be separated as a non-adsorbed phase component, that is, a raffinate component.

[0045]

According to the present invention, in producing 1,3,5-trimethylbenzene from a trimethylbenzene isomer mixture containing ethyltoluene, ethyltoluene is subjected to at least one of a deethylation reaction, a hydrodeethylation reaction, and a transalkylation reaction. 1,3,5-trimethylbenzene can be efficiently produced by combining the two reactions, the step of performing the isomerization reaction of trimethylbenzene, and the step of adsorbing and separating 1,3,5-trimethylbenzene.

[Brief description of the drawings]

FIG. 1 shows a step of performing at least one of a deethylation reaction, a hydrodeethylation reaction, and a transalkylation reaction of ethyltoluene and an isomerization reaction of trimethylbenzene, and adsorption separation of 1,3,5-trimethylbenzene. It is a figure which shows the process of performing typically.

FIG. 2 is a diagram schematically showing an adsorption separation operation using a simulated moving bed according to an embodiment of the present invention.

[Explanation of symbols]

 1 to 12: adsorption chamber 13: desorbent supply line 14: extract extraction line 15: isomer mixture supply line 16: raffinate extraction line 17: desorbent recovery line 18: valve

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (reference) C07C 15/02 C07C 15/02 // C07B 61/00 300 C07B 61/00 300 F term (reference) 4D017 AA03 BA04 CA01 4G069 AA03 AA08 AA09 BA01B BA01C BA07A BA07B BA45A BA45C BC02B BC09B BC64B BC64C BC68A BC75A CB02 DA06 EA02Y FA02 FB14 FB65 FC05 ZA06A ZA06B 4H006 AA02 AC27 AD17 BA16 BA21 C30 BA30 BA30 BA30 BA30 BA30 BA30

Claims (7)

[Claims] (1) In producing 1,3,5-trimethylbenzene from a trimethylbenzene isomer mixture containing ethyltoluene, (1) deethylation, hydrodeethylation, and transalkylation of ethyltoluene 1,3,5-trimethylbenzene, and (2) a step of adsorbing and separating 1,3,5-trimethylbenzene. Manufacturing method. 2. Deethylation reaction of (1) ethyltoluene,
2. The method according to claim 1, wherein in the step of performing at least one of a hydrodeethylation reaction and a transalkylation reaction and an isomerization reaction of trimethylbenzene, an acid catalyst is used in the presence of hydrogen. A method for producing 3,5-trimethylbenzene. 3. The method for producing 1,3,5-trimethylbenzene according to claim 2, wherein the acid-type catalyst is an acid-type zeolite. 4. The method for producing 1,3,5-trimethylbenzene according to claim 3, wherein the acid zeolite is an acid mordenite. 5. The method according to claim 2, wherein the acid type catalyst contains at least one metal selected from rhenium, nickel and platinum as a hydrogenation active metal. A method for producing 5-trimethylbenzene. 6. The method according to claim 1, wherein the adsorbent used in the step (2) of adsorbing and separating 1,3,5-trimethylbenzene is a faujasite-type zeolite. Production method of 1,3,5-trimethylbenzene. 7. The method according to claim 6, wherein the adsorbent contains at least one cation of potassium, silver and lead.
The method for producing 1,3,5-trimethylbenzene described in the above.