JPH11228455A - Production of useful substance - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method for producing a useful substance capable of continuously producing bisphenol A from acetone and phenol. SOLUTION: Bisphenol A is produced by a pseudo-moving layer type chromatographic separation method. The pseudo-moving layer type chromatographic separation method comprises carrying out an operation for feeding phenol into a system comprising plural filler-packed columns endlessly bound to each other to flow the phenol in one direction, an operation for feeding acetone into the system, an operation for extracting a liquid mush containing the produced bisphenol A produced by a catalytic reaction, an operation for extracting a liquid much containing water outside the system, and a pseudo- moving layer operation for intermittently moving a position for feeding and extracting the liquids for each column along the directions of the liquid flows in the system to apparently move the filler in each column in a direction opposite to the direction of the liquid flow, thus moving the bisphenol A in the direction of the liquid flow and apparently moving the water in the direction opposite to the direction of the liquid flow to continuously separating the water and the bisphenol A.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a method for producing a useful substance by a reaction, and bisphenol A by this method.
And a method for producing the same.

[0002]

2. Description of the Related Art Bisphenol A [2,2-bis (4-hydroxyphenyl) propane] is useful as a raw material for plastics such as polycarbonate. As a method for producing this bisphenol A, acetone and excess phenol are mixed in the presence of an acid catalyst. The reaction is well known. In this case, a strongly acidic cation exchange resin having a sulfonic acid group is used as the acid catalyst because it can be easily separated from the reaction solution after the reaction. It is also proposed to use an ion exchange resin containing both modified sulfonic acid type cation exchange groups and ordinary sulfonic acid type cation exchange groups modified with a sulfur amine compound in order to reduce the amount of by-product bisphenol A isomers. (Tokuhei 6-2713
No. 2, Japanese Patent Publication No. 55-16700, Japanese Unexamined Patent Publication No.
No. 89819, JP-A-6-340564, etc.).

[0003] It is known that in the method for producing bisphenol A using only a strongly acidic cation exchange resin having a sulfonic acid group as described above, an isomer of bisphenol A is by-produced. In contrast, the above method using an ion exchange resin containing both a modified sulfonic acid type cation exchange group modified with a sulfur-containing amine compound and a normal sulfonic acid type cation exchange group is advantageous in that the amount of isomers can be reduced. Although it is excellent, on the other hand, there is a problem that a special resin must be manufactured, which increases the cost, and there is a possibility that the sulfur-containing amine may contaminate the reaction solution.

In the conventional method, since a single column is filled with an ion exchange resin and reacted, water produced by the reaction is adsorbed on the ion exchange resin and the catalytic activity is significantly impaired. In addition, there is a problem that it is necessary to stop the apparatus at regular time intervals to perform a dehydration operation, which makes continuous production impossible.

As a method for continuously producing useful substances, a simulated moving bed type chromatographic separation method proposed in Japanese Patent Application Laid-Open No. 8-229306 is known. Therefore, it is considered that this method is applied to the production of bisphenol A. In this method, a reaction raw material is supplied to a raw material supply port of an apparatus, and an eluent not involved in the reaction is supplied from an eluent supply port, so that the reaction and the separation are simultaneously performed in the layer.

[0006]

However, in the simulated moving bed type chromatographic separation method proposed above for producing a useful substance, all the reactants are supplied to the raw material supply port, and the reaction is performed from the eluent supply port. Since the reaction and separation are performed simultaneously in the bed by supplying an eluent that does not participate, it is necessary to introduce components that do not participate in the reaction into the system, and a large amount of the reaction product extracted out of the system is eluted. There is a problem that the burden of the post-processing step of separating from the substrate is large. Also, one of the raw materials (in this case, phenol) as in the production of bisphenol A
If the supply of excess phenol is preferred to obtain a high conversion (see JP-B-55-16700), a large excess of phenol must be supplied, resulting in a quantitative excess. The supply rate of the supplied raw material increases, which causes a serious problem that it is difficult to secure a residence time in a zone where the reaction is to proceed, and it is difficult to appropriately maintain the moving speed of each component. Therefore, it is not suitable to use the simulated moving bed type chromatographic separation method proposed above for producing such a useful substance.

[0007] In view of these problems, the present invention proposes a novel method for producing a useful substance, which has never been available, by utilizing the advantages of a simulated moving bed type chromatographic separation method capable of continuous production.
Specifically, it proposes a method for producing useful substances using a simulated moving bed type chromatographic separation method that can appropriately provide reaction and separation without introducing components not involved in the reaction into the system. is there.

Another object of the present invention is to propose a method for producing a useful substance which can be suitably employed when one of the reactants is excessively required.

Still another object of the present invention is to provide a method for producing a useful substance which can reduce or eliminate the burden of post-treatment of a reaction product discharged out of the system and which can be continuously produced and has high productivity. There is a suggestion.

[0010]

According to a first aspect of the present invention, there is provided a method for producing a useful substance, comprising the steps of: connecting a plurality of towers each having a layer of a filler formed therein in an endless circulation type; The operation of flowing in one direction, the operation of supplying the first liquid to one of the liquid inlets provided to supply the liquid to the top of each column, and the first liquid of the liquid inlet being different An operation of supplying a second liquid acting as a developing agent and a solvent to the first liquid at the liquid inlet, and one of liquid outlets provided to withdraw liquid from the end of each column. An operation of extracting a liquid rich in the target substance to the outside of the system, an operation of extracting a liquid rich in a substance other than the target substance from the other of the liquid outlets to the outside of the system, The positions of the liquid inlet and liquid outlet for the supply and withdrawal of liquid are intermittently moved by one column along the liquid flow direction in the system, and By performing each of the operations of the pseudo-moving layer in which the filler is apparently moved in the direction opposite to the flow direction of the liquid, a substance having a low affinity for the filler is used for the operation of the pseudo-moving layer. Regardless, while moving in the direction of flow of the liquid, a substance having a strong affinity for the filler is apparently moved in the opposite direction to the flow direction of the liquid to continuously separate these substances having different affinities. According to the pseudo moving bed type chromatographic separation method in which the target substance and a substance other than the target substance are drawn out of the system from different liquid outlets, the first liquid supplied to the system is subjected to a chemical reaction. At least one of the two or more types of raw materials that produce a useful substance, and the second liquid has the above-mentioned action, and the remaining raw materials that chemically react with the raw material of the first liquid to produce a useful substance. Characterized as a substance

In the above description, the term “affinity” generally means that the slow and fast movement of each component, which appears when a component contained in a liquid to be treated is moved by an eluent in a chromatographic separation operation, depends on the packing material and each material. The components are defined as the magnitude of this influential force, as the components depend on the differences in their influencing affinities. The affinity is substantially the same as what is described as "adsorption", "sorption" and the like in the description of general simulated moving bed type chromatographic separation, and does not distinguish them. A component having a high affinity moves slowly in the system, so that the operation of the simulated moving bed usually causes the component to apparently move upstream in the flow direction of the liquid. Conversely, a component having a low affinity moves quickly in the system, and usually moves downstream in the liquid flow direction. The target substance may be a component having a strong affinity or a component having a weak affinity.

In the above description, the fact that the second liquid "acts as a developing agent and a solvent" means that the second liquid is a raw material contributing to the reaction, and at the same time, in the conventional simulated moving bed type chromatographic separation method. It means that it acts as an eluent introduced as a liquid that does not contribute to the reaction. Therefore, this second liquid is introduced into the system so as to exist in all the columns constituting the similar moving bed apparatus.

As a simulated moving bed type chromatographic separation apparatus used for carrying out such a method, for example, a four-zone simulated moving bed apparatus described in the following embodiment is disclosed. 62-91205
JP-A-4-22
The apparatus described in No. 7804 can be cited as an example. Liquids of two or more kinds of raw materials are introduced into the system from different liquid inlets (corresponding to the raw material supply port and the eluent supply port in the conventional apparatus). Then, the method of the present invention can be applied without any particular limitation using an apparatus based on a known simulated moving bed type chromatographic separation apparatus.

As the above-mentioned filler, for example, those having a separating ability and having a catalytic ability for the reaction can be used, and those having only a separating ability without a catalytic ability can be used. It can be determined according to the type of reaction to be used, conditions, separation conditions, and the like. For example, examples of the former filler include ion exchange resins and zeolites that are both a reaction catalyst and a chromatographic separating agent.

The reaction conditions for producing the useful substance are not particularly limited, as long as the reaction temperature, pressure, reaction time and the like satisfy the reaction conditions for producing the desired useful substance. In the above, the “chemical reaction” is not particularly limited, and may be any of a synthesis reaction, a decomposition reaction, a reaction using a catalyst, and the like. For example, it can be applied to the reaction to synthesize the target substance bisphenol A from acetone and phenol, and the reaction to synthesize oil-soluble phenol resin and alkylphenol (dodecylphenol, nonylphenol, octylphenol, etc.) used as surfactant from olefin and phenol. Also, it can be used for synthesis reactions of various esters and ethers.

According to the present invention, there is no need to introduce unnecessary components not involved in the reaction into the system, and it is also necessary to separate the component from other components in the step after the target substance is extracted out of the system. Or the burden is greatly reduced. In addition, for example, when one of the reaction raw materials (raw material) is excessively required to reduce by-products, the raw material is supplied into the system from different positions, so that the supply speed of the other reaction raw material is increased. This eliminates the need to operate the simulated moving bed under appropriate flow conditions.

In a second aspect of the present invention, there is provided a method for producing bisphenol A according to the above invention, wherein the raw material is used as a first liquid in a simulated moving bed type chromatographic separation apparatus filled with a filler in the form of hydrogen ions of a strongly acidic cation exchange resin. Acetone, one of the substances, is supplied, and phenol, another of the raw materials, is supplied in an excess state as a second liquid also serving as a developing agent and a solvent. , A reaction utilizing the catalytic activities of acetone and phenol is carried out, and at the same time, an operation of chromatographic separation for separately extracting bisphenol A and water out of the system is continuously carried out.

In the above, the apparatus of claim 1 can be used as a simulated moving bed type chromatographic separation apparatus. As the filler, an ordinary sulfonic acid type strongly acidic cation exchange resin which is a gel type and has a low degree of crosslinking can be used.

In the present invention, the useful substance (target substance) to be produced is bisphenol A, and the raw material of the first liquid supplied into the system of the simulated moving bed type chromatographic separation apparatus is acetone, a developing agent, and a solvent as a solvent. The raw material of the second liquid which is supplied in a large excess to the system for the function is phenol, and other substances (components) extracted out of the system as substances other than the target substance are water as a reaction product. It is. Bisphenol A is a component having low affinity for the filler, and water is a component having high affinity. In the method of the present invention, the reaction conditions are such that phenol is supplied in a large excess with respect to acetone, for example, as described in JP-A-6-3405 described above.
The optimum conditions can be determined by conducting a test in accordance with the conditions described in JP-A-64-64, etc., or according to the conditions.

According to the present invention, even when only a low-priced strongly acidic cation exchange resin having a sulfonic acid group is used, the produced bisphenol A is immediately extracted out of the system, and the phenol is always present in a large excess. Therefore, the isomer of bisphenol A is hardly produced as a by-product. Further, there is no possibility that the sulfur-containing amine compound will contaminate the reaction solution. Furthermore, since the water generated by the reaction is constantly drawn out of the system, the cation exchange resin in the form of a hydrogen ion can always keep its catalytic activity high.

In the present invention for producing bisphenol A, use of an ion exchange resin containing both a modified sulfonic acid type cation exchange group modified with a sulfur-containing compound and a usual sulfonic acid type cation exchange group as a filler is described. It is not excluded. In principle, these resins can be used. Therefore, if these resins are available at low cost and there are no industrial disadvantages, they can be used.

The invention of the apparatus for producing bisphenol A according to claim 4 is a system of a packed tower group in which a plurality of towers filled with hydrogen ion type strongly acidic cation exchange resin are connected endlessly, and acetone is supplied to the top of each tower. Acetone supply means for supplying acetone into the system from one of the liquid inlets provided so as to supply phenol to the top of each column from one of the liquid inlets provided to supply phenol to the system. Phenol supply means for supplying phenol, and bisphenol A produced by a catalytic reaction
Bisphenol A withdrawing means for extracting the bisphenol A liquid from one of the liquid outlets provided to drain the liquid abundant from the end of each column to the outside of the system; A water extraction means for extracting the water from one of the liquid outlets provided so as to be drawn out of the system from the end of the tower, and the positions of the liquid inlet and the liquid outlet for supplying and extracting these liquids within the system. Simulated moving bed operation means for intermittently moving one column at a time along the liquid flow direction and apparently moving the packing material in each column in the direction opposite to the liquid flow direction. And

According to this apparatus, as described in the second aspect of the present invention, it is possible to efficiently produce bisphenol A using only a strongly acidic cation exchange resin having a sulfonic acid group. That is, the produced bisphenol A is immediately taken out of the system, and phenol is always present in a large excess, so that the production can be carried out with almost no by-product of the isomer of bisphenol A. Further, since no sulfur-containing compound is used, there is no possibility of contamination of the reaction solution. Furthermore, since the water generated by the reaction is always drawn out of the system, the hydrogen ion type cation exchange resin can always keep its catalytic activity high.

[0024]

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS FIG. 1 is a flow chart showing the construction of a simulated moving bed type chromatographic separation apparatus used for producing bisphenol A by the method of the present invention.
The liquid flow state at a certain point in the middle of the intermittent movement of the withdrawal position is shown. (The flow of the liquid in the system, the supply of the liquid, and the liquid withdrawal at this point are indicated by bold lines. ).

In this figure, reference numerals 1 to 8 represent, for example,
Shown is a column filled with a sulfonic acid type strongly acidic cation exchange resin (hydrogen ion type) which is a gel type and has a low degree of crosslinking as a filler. They are connected by pipes so as to endlessly circulate (in the direction of the arrow in the figure) (* in the figure indicates that they are connected).

The first liquid (acetone) is supplied so that the first liquid and the second liquid can be supplied to the top of each of these towers 1 to 8 (lower end of FIG. 1 of each tower). ) And the supply pipe 11 for the second liquid (phenol + effluent) are connected to each other via an electromagnetic on-off valve.

In the figure, in order to avoid complication in the figure, the tower 5 is selected, an electromagnetic on-off valve 5a for supplying the first liquid from the supply pipe 10 to the tower 5 is used, and the second liquid is The electromagnetic on-off valves supplied from the supply pipe 11 are shown as 5b, and the symbols of these electromagnetic on-off valves for other towers are omitted, but when the electromagnetic on-off valves are described in relation to each tower, The symbols 1 to 8 of the respective towers are denoted by a or b to indicate the corresponding electromagnetic on-off valves. In addition, each tower 1-8
At the end of the column (upper end in FIG. 1 of each column), a raffinate containing bisphenol A as a target substance and an extract containing water as another substance other than the target substance are raffinated from these columns 1 to 8, respectively. The solenoid valve is connected to the extraction pipe 12 and the extraction pipe 13 via an electromagnetic on-off valve so that the raffinate can be extracted from the tower 5. The on-off valve is shown as 5c, the electromagnetic on-off valve for extracting the extract to the extraction pipe 13 is shown as 5d,
The notation in the drawing is omitted, and in the following description, c or d is added to the reference numerals 1 to 8 of each tower as described above.

In the apparatus of the present embodiment, an electromagnetic opening / closing type shutoff valve (a shutoff valve downstream of the tower 5 is typically used in the same manner as described above) to shut off the flow of liquid between the towers of the circulation pipe. A reference numeral 5s is shown, and if it is necessary to explain other towers, the explanation will be made by adding s to the reference numerals of the towers in the same manner as described above. For example, in the state shown in the figure, the effluent (phenol) is withdrawn from the end of the tower (tower 1 in the figure) upstream of the shut-off valve 1s) through the solenoid on-off valve 1e to the effluent (phenol) extraction pipe 15 and returned to the phenol supply system. Again to supply it into the system. This is done for the following reasons. That is, the first reason is to clarify all of the flow rates in the system and adjust the flow rate to an appropriate value by measuring the flow rate of the effluent. The second reason is that, by analyzing the composition of the effluent, the degree of the sneakage of the target substance, bisphenol A, to the extract side and the spillage of the non-target substance, water, to the raffinate side are confirmed. This is to properly set.

[0029]

EXAMPLE 1 A reaction in which one molecule of acetone and two molecules of phenol are used to generate and separate one molecule of a useful substance, bisphenol A, and one molecule of water other than the target substance is shown in FIG. Was carried out using

The apparatus is composed of eight stainless steel columns (towers with a heating jacket) having an inner diameter of 1 cm and a length of 30 cm.
8 are connected in an endless series, and all the columns contain 23.6 ml of a hydrogen ion form of Amberlyst 31 (trade name: manufactured by Rohm and Haas Co.), which is a strongly acidic cation exchange resin, as a filler. Each was filled.

The operation of this apparatus was controlled by controlling the opening and closing of an electromagnetic valve by a sequencer (not shown) to intermittently switch the flow path eight times to make one cycle. The bold line in the drawing indicates a state in which the liquid is flowing in a certain switching state (a state in which acetone is supplied to the column 5 and a phenol is supplied to the column 8) in one cycle. The liquid flow is an upward flow, and the circulating flow is once taken out of the system as an effluent before the place where the second liquid, phenol is supplied (the top of the column 8 in the state of FIG. 1), and is mixed with fresh phenol. Was supplied by the supply pump 111. All columns 1-8 were kept at a constant temperature with a water jacket. The number of columns in each zone was divided into four zones as two, one, four, and one in the downstream direction from the second liquid supply port. That is, in the state of FIG. 1, a component having a strong affinity for the filler from the supply port of phenol as the second liquid (the top of the column 8) to the extract extraction port (the end of the column 7). Two Zone IV to collect
One zone III from the extract outlet (column 7 column end) to the first liquid acetone supply port (column 5 top), and the raffinate extract port (column 2 column 2) from the first liquid supply port. 4) from zone II to the second liquid supply port (top of column 8)
One zone I for recovering a component having a low affinity up to one zone. These liquid supply ports and liquid discharge ports were shifted by one column in the downstream direction of the circulating flow of the liquid every predetermined time by switching the opening and closing of each of the electromagnetic on-off valves.

Bisphenol A was produced under the following conditions.

Reaction temperature 70 ° C. One cycle time 214.4 minutes Raw material Acetone Japanese Industrial Standard reagent special grade, purity 99.5% or more Raw material Phenol Japanese Industrial Standard reagent special grade, purity 99.0% or more Each supply flow rate and withdrawal flow rate acetone (stock solution) 0.12 ml / min phenol (from eluant supply port) 7.26 ml / min raffinate 1.45 ml / min extract 5.93 ml / min effluent 0.36 ml / min A raffinate solution and an extract solution having the following respective component concentrations were obtained as effluents of the seven cycles as respective divided solutions.

Raffinate liquid Extract liquid Bisphenol A 1.061 mol / l 0.002 mol / l Water 0.010 mol / l 0.260 mol / l Acetone 0.005 mol / l 0.002 mol / l Raffinate liquid The purity of bisphenol A excluding phenol therein was 99.8% on a mass basis, and no isomer of bisphenol A could be detected in each of the divided liquids. Assuming that the overall reaction rate of acetone is {(mol number of acetone in inlet−mol number of acetone in outlet) / mol number of acetone in inlet} × 100, this is 98.9%, and the yield of bisphenol A is {mol of exit bisphenol A}. If the number / mol of inlet acetone is x100, this is 98.6%, which is a value found in the literature, which is 69.5% of acetone conversion (Table 1 of Japanese Patent Publication No. 55-16700) and the conversion of acetone. 9
5.0% (Table 1 of JP-A-6-340564). The recovery rate of bisphenol A produced in the reaction in a raffinate solution was 99.3%,
Bisphenol A generated by the reaction could be efficiently recovered.

In order to isolate bisphenol A from the obtained raffinate solution, it can be separated, for example, by the following method according to a conventional method. That is, acetone and water are stripped to form an adduct crystal having a ratio of bisphenol A to phenol of 1: 1. After filtering, phenol is dissolved and removed with an organic solvent such as toluene.

[0036]

According to the present invention, when a reaction is carried out in a simulated moving bed by a simulated moving bed type chromatographic separation method, components which do not participate in the reaction are not introduced into the system. Can be given appropriately, and the effect of reducing the post-treatment load for separating the target substance of the reaction product extracted out of the system from other substances can be reduced or eliminated, and continuous production is possible. Thus, the target substance can be obtained with high productivity.

In particular, since the raw materials for the reaction are supplied from different supply ports into the simulated moving bed system, it is possible to prevent the supply rate from being extremely increased when it is desired to make one of the reaction raw materials excessive. Thus, the operation of the simulated moving bed can be performed under an appropriate flow rate condition, and the overall reaction rate can be increased.

In a reaction in which the production of by-products can be suppressed by supplying one of the reaction raw materials in excess,
This has the effect of reducing the amount of by-products and obtaining a liquid having a high content of the target component.

According to the second aspect of the invention, when producing bisphenol A from acetone and phenol, phenol can be supplied in a large excess, and the produced bisphenol A is immediately discharged out of the system. Therefore, even when only a strongly acidic cation exchange resin having a sulfonic acid group is used as a filler, it is possible to suppress the generation of isomers and obtain a product with a high conversion and a high purity. In addition, since water generated by the reaction is constantly extracted to the outside of the system, an excellent effect that continuous operation can be performed while maintaining a high catalytic activity of the hydrogen ion type cation exchange resin is exhibited.

[Brief description of the drawings]

FIG. 1 is a flowchart showing a schematic configuration of a simulated moving bed type chromatographic separation apparatus used in Example 1.

[Explanation of symbols]

1-8: Unit packed tower (1-8) a: Solenoid on-off valve (for acetone supply) (1-8) b: Solenoid on-off valve (for phenol + effluent supply) (1-8) c: ( Electromagnetic on / off valve (for extracting raffinate) (1-8) d: Electromagnetic on / off valve (for extracting extract) (1-8) e: Electromagnetic on / off valve (for extracting effluent) 5a: First liquid in column 5 5b: Electromagnetic on-off valve for supplying the second liquid to the tower 5 from the supply pipe 11 5c: Electromagnetic on-off valve for extracting the raffinate from the tower 5 to the extraction pipe 12 5d: For the extraction pipe 13 Electromagnetic on-off valve for extracting the extract from the tower 5 5e: Electromagnetic on-off valve for extracting the effluent from the tower 5 to the extraction pipe 15 5s: Valve for shutting off the flow of the liquid from the tower 5 to the tower 6 10: First liquid (Acetone) supply piping 101 : Supply pump 11: Supply pipe for the second liquid (phenol + effluent) 111: Supply pump 12: Raffinate extraction pipe 13: Extract extraction pipe 15: Efluent extraction pipe

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁶ Identification code FI C07C 37/20 C07C 37/20 39/16 39/16 (72) Inventor Takayuki Masuda 1-2-8 Shinsuna, Koto-ku, Tokyo Organo Corporation

Claims (4)

[Claims] An operation of flowing a liquid in one direction in a system in which a plurality of columns having a layer of a filler formed therein are connected in an endless circulation type;
An operation of supplying the first liquid to one of the liquid inlets provided to supply the liquid to the top of each tower, and the first liquid being supplied to a liquid inlet different from the first liquid among the liquid inlets. Supplying a second liquid that acts as a developing agent and a solvent to the liquid, and a liquid rich in the target substance from one of the liquid outlets provided to withdraw the liquid from the end of each column. Withdrawing a liquid rich in substances other than the target substance out of the system from another of the liquid outlets, and a liquid for supplying and extracting these liquids. Simulated movement in which the positions of the inlet and the liquid outlet are intermittently moved by one column along the liquid flow direction in the system, and the filler in each column is apparently moved in the direction opposite to the liquid flow direction. The operation of the bed and the operation of the bed are performed respectively, so that a substance having a low affinity for the filler can be removed from the liquid regardless of the operation of the simulated moving bed. In the direction of flow of the filler and apparently in the direction opposite to the flow direction of the liquid to continuously separate these substances having different affinities. A simulated moving bed type chromatographic separation method in which a substance and a substance other than the target substance are drawn out of the system from different liquid outlets, wherein the first liquid supplied to the system generates a useful substance by a chemical reaction. And at least one of the two or more types of raw materials to be used, and the second liquid is the remaining raw material that has the above-mentioned action and chemically reacts with the raw materials of the first liquid to produce a useful substance. A method for producing a useful substance, comprising: 2. The bisphenol A according to claim 1, wherein the filler is a hydrogen ion form of a strongly acidic cation exchange resin, the first liquid is acetone, and the second liquid is phenol. Production method. 3. An operation of supplying phenol to a system of a plurality of packed packed columns connected endlessly and flowing it in one direction, an operation of supplying acetone to the system, and a liquid containing a large amount of bisphenol A produced by a catalytic reaction. To remove the liquid containing a large amount of water from the system, and to intermittently move the supply and withdrawal positions of these liquids one by one along the liquid flow direction in the system. The operation of the pseudo moving bed in which the packing material in each column is apparently moved in the direction opposite to the liquid flow direction is performed, and bisphenol A is moved in the liquid flow direction, and water is apparently observed. Is a simulated moving bed type chromatographic separation method in which water and bisphenol A are continuously separated by moving in the direction opposite to the flow of the liquid, and each is continuously withdrawn. 4. A system comprising a group of packed columns in which a plurality of columns packed with a strongly acidic cation exchange resin in the form of hydrogen ions are connected endlessly, and one of a liquid inlet provided to supply acetone to the top of each column. Acetone supply means for supplying acetone into the system from one side, phenol supply means for supplying phenol into the system from one of the liquid inlets provided to supply phenol to the top of each column, and a catalytic reaction Bisphenol A withdrawing means for extracting the bisphenol A liquid from one of the liquid outlets provided so as to drain the liquid rich in bisphenol A generated from the end of each column to the outside of the system; A water extracting means for extracting the liquid from one of the liquid outlets provided to drain the liquid from the end of each column to the outside of the column, and positions of a liquid inlet and a liquid outlet for supplying and extracting these liquids Along the liquid flow direction in the system A simulated moving bed operating means for intermittently moving one column at a time to apparently move the filler in each column in the direction opposite to the flow direction of the liquid; apparatus.