JPH11286457A - Continuous catalytic reduction of organic compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method for continuously catalytically reducing an organic compound, not having a limitation on the employment of a hydrogenation catalyst and not requiring a complicated operation for recycling the hydrogenation catalyst for the catalytic hydrogenation. SOLUTION: This method for continuously catalytically reducing an organic compound comprises using a stirring tank type reactor 1 in which a filter 4 for the solid-liquid separation of a reaction solution from a hydrogenation catalyst is disposed so that the whole filtration surface of the filter is brought into contact with the reaction solution, charging the organic compound as a raw material compound from a charging pipe 2 into the reactor 1 having the hydrogenation catalyst therein, further charging hydrogen gas from a charging pipe 3 into the reactor, and simultaneously discharging the reaction solution subjected to the solid-liquid separation from the hydrogenation catalyst by the use of the filter 4 from a discharging pipe 5.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a method for continuously reducing an organic compound in the presence of a hydrogenation catalyst, and more particularly, to a method for reducing hydrogen and an organic compound as a raw material (hereinafter simply referred to as a raw material compound). The present invention relates to a method for continuously reducing a reaction solution while continuously introducing the reaction solution into the reactor and continuously flowing the reaction solution from the reactor.

[0002]

2. Description of the Related Art Catalytic reduction is an important reaction in industrial production of various organic compounds, and various methods for continuously reducing organic compounds have been proposed. For example, (1) a tubular reactor is filled with a hydrogenation catalyst as a fixed bed, and a raw material compound and hydrogen are continuously introduced from a lower portion of the reactor,
And a method of performing catalytic reduction while continuously flowing the reaction solution and unreacted hydrogen from the upper part of the reactor, (2) suspending the hydrogenation catalyst in a raw material compound or a mixture of a raw material compound and a solvent,
A method in which this suspension and hydrogen are continuously supplied to a tower-type reactor to perform catalytic reduction, and a reaction solution containing a hydrogenation catalyst and unreacted hydrogen are continuously discharged from the reactor; (3) hydrogen A slurry of a hydrogenation catalyst and a solvent, a raw material compound, and hydrogen are continuously supplied to a stirred tank reactor to perform catalytic reduction, and a reaction solution containing a hydrogenation catalyst and unreacted hydrogen are continuously discharged from the reactor. There are methods.

[0003]

In the conventional method (1), the pressure loss in the catalyst layer packed as the fixed layer becomes a problem, so that a large resistance is generated in the flow of the raw material compounds and the reaction solution. It is necessary to secure a gap by using a hydrogenation catalyst having a large particle diameter so as not to cause such a problem. For this reason, a hydrogenation catalyst from which a particle having a large particle size cannot be obtained or a hydrogenation catalyst having low mechanical strength and easy to be pulverized are unsuitable for filling and using as a fixed bed because of a large pressure loss. In addition, in catalytic reduction in which the diffusion of the raw material compound into the catalyst pores is rate-determining, the particle size must be reduced in order to increase the effective coefficient of the hydrogenation catalyst. This is problematic, and it is difficult to carry out the method (1) in which the hydrogenation catalyst is packed and used as a fixed bed.

[0004] In the method (2), the hydrogenation catalyst comprises:
The suspension is supplied to the reactor as a suspension with the starting compound, and flows out of the reactor in a state of being suspended in the reaction solution. Therefore, it is necessary to use a hydrogenation catalyst having a specific gravity that can maintain a suspended state at all times. In the method (2), the hydrogenation catalyst flowing out from the reactor together with the reaction solution is separated from the reaction solution by solid-liquid separation outside the reactor in order to recycle the hydrogenation catalyst for catalytic reduction. A complicated operation such as mixing with a compound and returning to the inside of the reactor is required.

[0005] In addition, the method (3) is also a method in which the hydrogenation catalyst is discharged from the reactor together with the reaction solution, and thus the same operation as in the above (2) for circulating and reusing the hydrogenation catalyst for catalytic reduction. Cost.

In the catalytic reduction, for example, the catalytic reduction of an unsaturated hydrocarbon group such as an aromatic ring, a carbonyl group, a cyano group or a nitro group, or the reaction of a primary or secondary amine with a carbonyl compound and hydrogen. There are many types of starting compounds and reactions, such as reductive alkylation. In order to produce the target product selectively and in a high yield in each catalytic reduction, an optimal hydrogenation catalyst must be used. However, the methods (1) and (2) are limited in the hydrogenation catalysts that can be used as described above, and therefore the catalytic reduction that can produce the target product selectively and in high yield by these methods is limited. There is a problem. This problem can be solved by the method (3), but the method (3) still has a problem that a complicated operation is required to recycle and reuse the hydrogenation catalyst.

The present invention relates to a method for continuously reducing an organic compound by catalytic reduction, which does not limit the use of a hydrogenation catalyst and requires a complicated operation for circulating and reusing the hydrogenation catalyst for catalytic reduction. It is an object of the present invention to provide a method that does not perform the above.

[0008]

Means for Solving the Problems The present inventor has made intensive studies to solve the above-mentioned problems. As a result, in the continuous catalytic reduction of organic compounds, a stirred tank reactor is used as the reactor, and a filter for solid-liquid separation of the reaction solution and the hydrogenation catalyst is used so that the entire filtration surface is in contact with the reaction solution. If it is disposed inside the reactor, the hydrogenation catalyst and the reaction solution can be separated into solid and liquid by a filter, and only the reaction solution can flow out of the reactor to keep the hydrogenation catalyst inside the reactor. It has been found that the organic compound can be continuously catalytically reduced by continuously supplying the organic compound and hydrogen into the inside of the reactor, thereby completing the present invention.

That is, the present invention provides a method for continuously reducing an organic compound by using a stirred tank type reactor as a reactor, and a filter for solid-liquid separation of a reaction solution and a hydrogenation catalyst. The present invention relates to a method for continuously catalytically reducing an organic compound, wherein the organic compound is disposed inside the reactor so as to come into contact with a reaction solution.

The present invention does not require a complicated operation for recycling and reuse of the hydrogenation catalyst, and uses a hydrogenation catalyst most suitable for the catalytic reduction to be carried out in high yield and selective use. This is an excellent method that can produce the desired product.

[0011]

BEST MODE FOR CARRYING OUT THE INVENTION The catalytic reduction in the present invention is carried out by a gas-liquid-solid method using a solid hydrogenation catalyst, hydrogen gas and a raw material compound in a reactor or a solution obtained by dissolving the raw material compound in a solvent. Is a three-phase catalytic reduction of The target product produced by the catalytic reduction of the present invention is a solution dissolved in a liquid or a solvent inside the reactor, which is separated from the hydrogenation catalyst by a filter in a solid-liquid manner and flows out of the reactor.

The catalytic reduction that can be carried out according to the present invention is not particularly limited as long as it is the above-mentioned three-phase catalytic reduction, and various conventionally known catalytic reductions can be performed. For example,
Catalytic reduction of compounds having a carbonyl group, cyano group, nitro group, aromatic ring, carboxyl group or a group derived therefrom, reduction by reaction of a carbonyl compound with ammonia, primary amines or secondary amines and hydrogen Alkylation and the like.

These catalytic reductions include, for example, catalytic reduction of nitriles, catalytic reduction of an aromatic ring of a nitrogen-containing heteroaromatic compound, and reductive reaction of reacting a carbonyl compound with ammonia, a primary or secondary amine and hydrogen. Various amines can be produced by alkylation or the like, and an alkyl-substituted nitrogen-containing heteroaromatic compound can be produced by reacting the nitrogen-containing heteroaromatic compound with an aliphatic alcohol or the like and hydrogen. The present invention is suitable for such catalytic reduction of a nitrogen-containing compound. In the production of primary amines by catalytic reduction of nitriles, when catalytic reduction is carried out batchwise, ammonia is used to prevent a decrease in the yield of primary amines due to by-products such as secondary amines. However, if the catalytic reduction of nitriles is carried out continuously, preferably as in the present invention, the production of by-products can be suppressed by reducing the amount of ammonia used or without using ammonia and suppressing the production of by-products. Primary amines can be produced in high yield.

The hydrogenation catalyst in the present invention is not particularly limited as long as it is a solid catalyst which is insoluble in the reaction solution, and an appropriate hydrogenation catalyst capable of selectively producing a desired product in a high yield according to the reaction is appropriately selected. And use it. Specific examples of the hydrogenation catalyst used in the present invention include, for example, platinum group elements (ruthenium, rhodium, palladium, osmium, iridium,
Hydrogenation catalysts containing at least one metal selected from the group consisting of platinum), iron group elements (iron, cobalt, nickel) and copper and / or a compound thereof as an active component of the catalyst are included. More specifically, the at least one metal and / or a compound thereof is activated carbon, alumina, silica-alumina, barium sulfate, calcium carbonate, barium carbonate,
Examples thereof include those supported on an inert carrier such as diatomaceous earth, Raney catalysts such as Raney nickel, Raney cobalt, and Raney copper, and metal oxides such as platinum oxide, ruthenium oxide, and cobalt oxide. These hydrogenation catalysts include those partially poisoned by a catalyst poison (for example, a white metal catalyst treated with a lead compound or the like, a nickel catalyst treated with a sulfur compound or the like), and the like.

An example of the embodiment of the present invention will be described with reference to FIG. According to the present invention, a raw material compound is introduced into a stirred tank reactor 1 in which a hydrogenation catalyst is present from an introduction pipe 2 and hydrogen is introduced from an introduction pipe 3, and a reaction solution is supplied from an outlet pipe 5 via a filter 4. The catalytic reduction is carried out while flowing out of the reactor. The hydrogenation catalyst and the reaction liquid are solid-liquid separated by the filter 4, and the reaction liquid excluding the hydrogenation catalyst is discharged from the outlet pipe 5. Since the hydrogenation catalyst remains in the reactor, continuous catalytic reduction is performed by continuously introducing the raw material compound and hydrogen.

In starting the process of the present invention, for example, a raw material compound and a hydrogenation catalyst are first charged into a stirred tank reactor, and hydrogen is introduced from an introduction pipe to complete batchwise catalytic reduction or stirring. A target compound and a hydrogenation catalyst are charged into a tank reactor. Thereafter, by continuously introducing the starting compound and hydrogen into the reactor, and continuously flowing out the reaction solution from the reactor, the catalytic reduction can be continuously performed.

Since the catalytic reduction is preferably carried out under hydrogen pressure, a pressurized reactor is used as the stirred tank type reactor, but the present invention is not limited to this.

When performing catalytic reduction using a plurality of starting compounds as in the case of reductive alkylation, even if a mixture of the starting compounds is introduced from one introduction pipe, a stirred tank reactor having a plurality of introduction pipes is used. And the respective starting compounds may be introduced into the reactor from separate introduction tubes. The starting compound and hydrogen may be introduced into the reaction solution, or either or both of them may be introduced from above the surface of the reaction solution inside the reactor. The introduction of hydrogen into the reaction solution is performed in a gas-liquid-solid phase.
This is preferred because of good phase contact.

Since the filter in the present invention is arranged so that the entire filter surface is in contact with the reaction solution, the hydrogenation catalyst separated from the reaction solution and the solid-liquid can be easily removed from the filter filtration surface by the stirred reaction solution. , The clogging of the filter and accumulation of the hydrogenation catalyst on the filter filtration surface can be suppressed, and an increase in pressure loss in solid-liquid separation can be prevented. In the present invention, a filter having a size corresponding to the particle size of the hydrogenation catalyst used for the catalytic reduction is appropriately selected and used. FIG. 2 shows an example of the filter of the present invention. The filter 4 in FIG. 2 is a cylindrical filter whose almost entire surface is a filtration surface, and solid-liquid separation of the hydrogenation catalyst and the reaction solution is performed on almost the entire surface of the filter. Only the solid-liquid separated reaction liquid flows into the filter, is sent to the outlet pipe 5, and flows out of the reactor. The shape of the filter is not particularly limited. In addition to the cylindrical shape such as the above-described cylindrical shape, a plate-shaped filter may be provided at the inlet of the reaction solution in the outlet pipe as shown in FIG. Examples of the filter used in the present invention include a sintered metal filter, a sintered wire mesh filter, a porous ceramic filter, a wire slit filter, a metal membrane filter, and a metal fiber filter. In particular, a sintered wire mesh filter [for example, a rigid mesh filter:
Trade name (Nippon Pall Co., Ltd.)] is a preferable filter because clogging by a hydrogenation catalyst hardly occurs and pressure loss in solid-liquid separation hardly increases.

The introduction rate of the starting compound and the outflow rate of the reaction solution for performing the catalytic reduction of the present invention differ depending on the catalytic reduction to be carried out and cannot be determined uniquely. The time may be controlled so as to be a time necessary for sufficiently proceeding the catalytic reduction. The average residence time for sufficiently proceeding the catalytic reduction can be easily determined by preliminary experiments. Since the average residence time can be easily controlled by the outflow rate of the reaction solution, the starting compounds are introduced so that the liquid amount inside the reactor is kept constant according to the outflow rate of the reaction solution.

The linear velocity of the reaction solution relative to the surface area of the filtration surface of the filter is generally 0.05 to 0.7 m / hr, preferably 0.1 to 0.5 m / hr, more preferably 0.1 to 0.5 m / hr.
The solid-liquid separation of the hydrogenation catalyst and the reaction solution at 2 to 0.4 m / hr to allow the reaction solution to flow out causes clogging of the filter and accumulation of the hydrogenation catalyst on the filtration surface of the filter. This is preferable because it becomes difficult to suppress an increase in pressure loss in solid-liquid separation.

Since the reaction solution flowing out of the reactor does not contain a hydrogenation catalyst, the target product can be easily isolated by directly performing distillation or the like.

[0023]

The present invention will be described in more detail with reference to the following Examples, but the present invention is not limited by the following Examples.

Example 1 Using the reactor shown in FIG. 1, dimethylaminoethylamine was produced. A stirred tank reactor 1 is a pressurized reactor having a capacity of 500 ml having a stirrer, and a filter 4 is a cylindrical sintered metal filter having a structure shown in FIG. 2 and having a diameter of 7.5 mm and a height of 13 mm (filter surface area: 3.5 c).
m ² ). 125 g of dimethylaminoethylamine and 12.5 g of Raney cobalt were charged into the stirred tank reactor 1, and hydrogen was introduced from the introduction pipe 3 while heating and stirring.
The temperature was set to 0 ° C. and 4.9 MPa (50 kgf / cm ² ). Then, dimethylaminoacetonitrile is introduced from the introduction tube 2, and Raney cobalt and the reaction solution are separated into solid and liquid by the filter 4, and the reaction solution is discharged from the outflow tube 5 to keep the content of the reactor constant. The reaction was performed at the above temperature and pressure. Dimethylaminoacetonitrile was introduced at an introduction rate of 47 g / hr, and the reaction solution was allowed to flow out such that the filtration linear velocity of the reaction solution in the filter 4 became 0.17 m / hr. Since hydrogen was consumed by the reaction, hydrogen was introduced successively and maintained at the above pressure. The effluent obtained by the above operation up to 6 hours from the start of the introduction of dimethylaminoacetonitrile was distilled to obtain dimethylaminoethylamine in a yield of 95.5%.

COMPARATIVE EXAMPLE 1 240 g of dimethylaminoacetonitrile and 48 Raney cobalt were placed in a 1-liter electromagnetically stirred autoclave.
g, and 25 g of ammonia was introduced with stirring to obtain a temperature of 24 ° C. and 0.49 MPa (5.0 kgf / cm ² ). Hydrogen was introduced into the mixture at 100 ° C. and 4.9 MPa (5
0 kgf / cm ² ). Since hydrogen was consumed by the reaction, hydrogen was successively introduced and maintained at the above pressure. After completion of the reaction, the reaction mixture was cooled and then filtered to remove the catalyst, and the obtained filtrate was distilled to obtain dimethylaminoethylamine in a yield of 90.7%.

Example 2 Using the same reaction apparatus as in Example 1, 3-methoxypropylamine was produced. A reactor was charged with 100 g of 3-methoxypropylamine and 10 g of Raney cobalt,
50 g of 3-methoxypropionitrile from the inlet tube 2
The reaction was carried out in the same manner as in Example 1 except that the reaction liquid was introduced from the outlet pipe 5 so that the filtration linear velocity of the reaction liquid in the filter 4 was 0.17 m / hr. The effluent up to 7 hours after the start of introduction of 3-methoxypropionitrile was distilled to obtain 3-methoxypropylamine in a yield of 93.5%.

Comparative Example 2 400 g of 3-methoxypropionitrile and Raney cobalt 80 were placed in a 1-liter electromagnetically stirred autoclave.
g, and 40 g of ammonia was introduced with stirring. Hydrogen was introduced into the mixture at 100 ° C. and 4.9 MPa (5
0 kgf / cm ² ). Since hydrogen was consumed by the reaction, hydrogen was successively introduced and maintained at the above pressure. After the end of the reaction, the reaction mixture was cooled and then filtered to remove the catalyst, and the obtained filtrate was distilled to give 3- (90.4%) yield.
Methoxypropylamine was obtained.

Example 3 Using the same reactor as in Example 1, 3-amino-1-propanol was produced. 3-amino-1-
100 g of propanol and 10 g of Raney cobalt were charged, and a solution in which 16% by weight of ammonia was dissolved in 1 part by weight of 3-hydroxypropionitrile at room temperature was introduced at 42 g / hr from the inlet tube 2. The procedure was performed in the same manner as in Example 1 except that the reaction solution was allowed to flow out of the outflow pipe 5 so that the speed was 0.10 m / hr.
The effluent up to 17 hours from the start of the introduction of the solution consisting of 3-hydroxypropionitrile and ammonia was distilled to give 3-amino-1-propanol in a yield of 88.2%.

Comparative Example 3 3-Hydride was added to a 1-liter electromagnetic stirring type autoclave.
Roxypropionitrile 300g and Raney cobalt 3
0 g was charged, and 76 g of ammonia was introduced with stirring.
Was. Hydrogen was introduced into the mixture at 100 ° C. and 4.9 MPa (5
0kgf / cm ^Two). The reaction consumes hydrogen
Therefore, hydrogen was successively introduced and maintained at the above pressure. End of reaction
Thereafter, the reaction mixture is cooled and then filtered to remove the catalyst by filtration.
Then, the obtained filtrate was distilled to give 3-7.9 with a yield of 87.9%.
Amino-1-propanol was obtained.

Example 4 Using the same reactor as in Example 1, benzylamine was produced. A reactor was charged with 80 g of benzylamine, 4.0 g of ammonia, 12 g of Raney cobalt and 40 g of methyl alcohol.
g / hr, and the same procedure as in Example 1 was carried out, except that the reaction solution was discharged from the outlet pipe 5 so that the filtration linear velocity of the reaction solution in the filter 4 became 0.17 m / hr. The effluent from the beginning of the introduction of benzonitrile to 8 hours was distilled to obtain benzylamine in a yield of 94.2%.

Comparative Example 4 300 g of benzonitrile, 10 g of water and 30 g of Raney cobalt were charged into a 1-liter electromagnetically stirred autoclave, and 22 g of ammonia was introduced with stirring. Hydrogen was introduced into the mixture, and the temperature was increased to 100 ° C. and 4.9 MPa (50 kg
f / cm ² ). Since hydrogen was consumed by the reaction, hydrogen was successively introduced and maintained at the above pressure. After completion of the reaction, the reaction mixture was cooled, then filtered to remove the catalyst, and the obtained filtrate was distilled to obtain benzylamine in a yield of 87.5%.

Example 5 N, N, N ', N'-tetramethylethylenediamine was produced using the reactor shown in FIG. The stirred tank reactor 1 and the filter 4 are the same as in the first embodiment. In a reactor, 69.6 g of N, N, N ', N'-tetramethylethylenediamine, 87.2 g of methyl alcohol, 43.
2 g and 0.76 g of 5% by weight palladium / carbon (50% by weight water-containing product) were charged.
A 5% by weight aqueous solution of formaldehyde was simultaneously introduced at a rate of 80.6 g / hr, and 5% by weight palladium / carbon was filtered off with a filter 4 and passed through the outlet pipe 5 so that the filtration linear velocity of the reaction solution in the filter 4 became 0.34 m / hr. The procedure was performed in the same manner as in Example 1 except that the reaction solution was discharged. The effluent up to 8 hours after the introduction of the ethylenediamine and the 47% by weight aqueous formaldehyde solution was distilled to obtain 94.2%
N, N, N ', N'-tetramethylethylenediamine was obtained in a yield of

Example 6 Piperidine was produced using the same reactor as in Example 1. 68.0 g of piperidine and 7.73 g of 5% by weight ruthenium / carbon (50% by weight water-containing product) were charged into the reactor, and hydrogen was introduced from the hydrogen introduction pipe 3 while heating and stirring, and 110 ° C., 4.9 MPa (50 kgf / cm ² ). Then, pyridine was introduced at 34.0 g / hr,
The filter 4 was filtered with 5 wt% ruthenium / carbon, and the linear velocity of the reaction solution in the filter 4 was 0.11 m
/ Hr in the same manner as in Example 1, except that the reaction solution was allowed to flow out of the outflow pipe 5 so as to be / hr. The effluent was distilled up to 8 hours after the introduction of pyridine to obtain piperidine in a yield of 95.4%.

Example 7 Benzylamine was produced using the reactor shown in FIG. The stirred tank reactor 1 is a pressurized reactor having a capacity of 200 liters having a stirrer, and the filter 4 is a cylindrical sintered wire mesh filter having a structure shown in FIG. 2 and having a diameter of 60 mm and a height of 180 mm (trade name: Rigimesh filter) , Nippon Pall Co., Ltd.) and four of them were attached to the outflow pipe 5 (total surface area of the filter: 0.1357 m 2). 97 kg of benzylamine, 7 kg of ammonia, and 12 kg of Raney cobalt were charged into a reactor, and hydrogen was introduced from the hydrogen introduction pipe 3 while heating and stirring, and the mixture was heated at 100 ° C. and 4.9 MPa (50 kPa).
gf / cm ² ). Next, benzonitrile was introduced from the inlet tube 2 and the reaction solution from which Raney cobalt was filtered off by the filter 4 was allowed to flow out from the outlet tube 5 to carry out the reaction at the above temperature and pressure while keeping the content of the reactor constant. Was done. Benzonitrile was introduced at 50 kg / hr,
The outflow of the reaction solution was performed so that the filtration linear velocity of the reaction solution in the filter 4 became 0.37 m / hr. Since hydrogen was consumed by the reaction, hydrogen was introduced successively and maintained at the above pressure. The effluent obtained by the above operation from the start of the introduction of benzonitrile to 145 hours was distilled to 98.7%
Benzylamine was obtained in a yield of.

Example 8 The procedure of Example 7 was repeated except that 80 kg of diethylaminopropylamine and 12 kg of Raney cobalt were charged into the reactor and the reaction was carried out while introducing diethylaminopropionitrile. However, diethylaminopropionitrile was kept at 27.5 k for 106.5 hours after the start of the introduction of diethylaminopropionitrile.
g / hr, and the reaction solution was discharged from the outlet pipe 5 so that the filtration linear velocity of the reaction solution in the filter 4 became 0.24 m / hr. Thereafter, diethylaminopropionitrile was added to the reaction solution at 40 g for 214.5 hours. The reaction solution was allowed to flow out so that the filtration linear velocity became 0.37 m / hr. The effluent from the beginning of introduction of diethylaminopropionitrile to 214.5 hours was distilled to 92.3 hours.
% Yield of diethylaminopropylamine was obtained.

Example 9 Using the same reactor as in Example 1, 3-methylaminopropylamine was produced. The same procedure as in Example 1 was carried out except that 100 g of 3-methylaminopropylamine and 10 g of Raney cobalt were charged into the reactor, and 3-methylaminopropionitrile was introduced at a rate of 50 g / hr from the inlet tube 2 to 87.0% 3-Methylaminopropylamine was obtained in a yield.

COMPARATIVE EXAMPLE 5 In a 1-liter electromagnetic stirring type autoclave, 440 g of 3-methylaminopropionitrile and 79.2 g of Raney cobalt were charged, and 49 g of ammonia was introduced with stirring, and 18.5 ° C. and 0.18 MPa ( 1.8kgf /
cm ² ). Hydrogen is introduced into the mixture at 100 ° C.
9 MPa (50 kgf / cm ² ). Since hydrogen was consumed by the reaction, hydrogen was successively introduced and maintained at the above pressure. After completion of the reaction, the reaction mixture was cooled and then filtered to remove the catalyst, and the obtained filtrate was distilled to obtain 3-methylaminopropylamine in a yield of 80.1%.

[Brief description of the drawings]

FIG. 1 is a diagram showing a configuration of a reaction apparatus for carrying out the present invention.

FIG. 2 is a diagram showing an outline of solid-liquid separation of a hydrogenation catalyst and a reaction solution in the present invention.

FIG. 3 is a diagram showing an outline of solid-liquid separation of a hydrogenation catalyst and a reaction solution in the present invention.

FIG. 4 is a diagram showing a configuration of a reaction apparatus for carrying out the present invention.

FIG. 5 is a diagram showing a configuration of a reaction apparatus for carrying out the present invention.

[Explanation of symbols]

1: stirred tank reactor, 2: inlet tube, 3: inlet tube (hydrogen), 4: filter, 5: outlet tube

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁶ Identification code FI C07C 213/02 C07C 213/02 215/08 215/08 217/08 217/08 217/26 217/26 // C07B 61/00 C07B 61/00 C 300 300 (72) Inventor Kenichi Kagugawa 25th Kita-sode, Sodegaura-shi, Chiba

Claims (3)

[Claims] In a method for continuously reducing an organic compound, a stirred tank reactor is used as a reactor, and a filter for solid-liquid separation of a reaction solution and a hydrogenation catalyst is provided with a filter whose entire filtration surface corresponds to the reaction solution. A method for continuously catalytically reducing an organic compound, wherein the organic compound is disposed inside the reactor so as to be in contact with the organic compound. 2. The method according to claim 1, wherein the filter is a sintered wire mesh filter. 3. The solid-liquid separation of the reaction solution and the hydrogenation catalyst is performed so that the filtration linear velocity of the reaction solution with respect to the surface area of the filter filtration surface is 0.05 to 0.7 m / hr. The described method.