JP2003028792A - Reaction control system for aqueous powder substance and manufacturing method of diphenyl sulfone compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a reaction control system for an aqueous powder substance for measuring a water content of the aqueous powder substance as a reaction material by means of an easy, quick, and accurate measurement method and calculating the water content of the aqueous powder substance and a usage of a reactant to be brought into reaction with the reaction material from the measurement result and to provide a diphenyl sulfone compound manufacturing method using this reaction control system. SOLUTION: This reaction control system for controlling reaction between the aqueous powder substance as the reaction material and the reactant is provided with a means of applying ionizing radiation to the aqueous powder substance and detecting a change in light quantity of reflected or permeated ionizing radiation for measuring the water content of the aqueous powder substance and a means of calculating a predetermined reaction condition of the reaction on the basis of the measured weight and water content of the aqueous powder substance. This reaction control system is used for this manufacturing method of a diphenyl sulfone compound.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a water-containing powder characterized by measuring the water content of a water-containing powdery material as a reaction raw material, and calculating and managing the reaction conditions of a chemical reaction using the reaction raw material from the measurement results. TECHNICAL FIELD The present invention relates to a reaction management system for a particulate matter and a method for producing a diphenylsulfone compound to which the reaction management system is applied.

[0002]

2. Description of the Related Art Conventionally, as a means for simply measuring the water content of powdered substances such as instant coffee and wheat flour, a fixed amount of these powdered substances are conveyed by a belt conveyor and the upper part of the belt conveyor is conveyed. There is known a method of measuring the water content of a powdery substance by attaching an automatic moisture measuring device, irradiating the powdery substance to be conveyed with infrared rays, and detecting a change in the amount of infrared light reflected or transmitted therethrough. (JP-A-61-4947, JP-A-61-2974)
No. 1, JP-A-61-29742, JP-A-4-
See JP-A-286937, JP-A-4-286938 and the like. ).

On the other hand, in the process of producing a chemical substance in which a reaction material is reacted with a reaction raw material (substrate) to obtain a target substance,
In the case where the reaction raw material is a powder containing water (hereinafter, referred to as “hydrous powder” in the present invention) or in order to reduce the manufacturing cost, the unreacted reaction raw material in a water-containing state from the reaction treatment liquid is used. There is a case where it is desired to collect (hereinafter, this collected product may be referred to as a “reaction collected product”) and use it again in the reaction.

Further, in order to carry out the reaction accurately by using the water-containing powder or the reaction recovered product, water is completely removed from the water-containing powder or the reaction recovered product, or the water-containing powder or the reaction recovered product is used. It is necessary to measure and understand the content of the solvent such as water contained in the reaction product.

However, in the case of completely removing water from the water-containing powdery substance or the reaction recovered substance, a separate drying facility is required, and it takes a long time for drying, which increases the manufacturing cost. Furthermore, there is little need to remove water if it does not participate in the reaction or if water can be used as the reaction solvent.

On the other hand, in the case of measuring the water content contained in the water-containing powder or the reaction product, for example, a method of sampling and manually measuring the water content may be considered, but the measurement work is It is not preferable in terms of work efficiency because it is complicated and requires a long time for measurement. Further, the water content changes with the passage of time due to the evaporation of water.

Therefore, particularly in the actual manufacturing process, the water content of the water-containing powdery material of the reaction raw material is measured,
From the obtained measurement results, it has been necessary to easily and quickly calculate and manage the amounts of the reaction raw materials, the reactants to be reacted therewith, the solvent and the like.

[0008]

DISCLOSURE OF THE INVENTION The present invention has been made in view of the above circumstances, and measures the water content of a water-containing powdery material as a reaction raw material using a simple, quick and accurate measuring method. An object of the present invention is to provide a reaction management system for a water-containing powdery substance, which calculates the water content contained in the water-containing powdery substance and the amount of a reactant or the like to be reacted with a reaction raw material from the measurement results. Another object of the present invention is to provide a method for producing a diphenyl sulfone compound to which the reaction management system is applied.

[0009]

[Means for Solving the Problems] In order to solve the above problems,
The present invention is, firstly, a reaction management system for managing a reaction condition for reacting a water-containing powder material as a reaction raw material with a reaction agent, wherein the water-containing powder material is irradiated with ionizing radiation to reflect or transmit the ionization radiation. By detecting the change in the light amount of the ionizing radiation, means for measuring the water content of the water-containing powder,
There is provided a reaction management system for a water-containing powdery substance, which has a means for calculating a predetermined reaction condition of the reaction based on the weight of the water-containing powdery substance whose water content is measured and the water content thereof.

A first invention of the present application is a reaction management system for managing reaction conditions for reacting a water-containing powder material as a reaction raw material with a reaction agent, which stores a water-containing powder material and conveys a predetermined amount thereof. Storage means for sending to the means, a transport means for transporting the water-containing powdery material sent from the storage tank, in the process of transporting the water-containing powdery material, irradiating the water-containing powdery material with ionizing radiation, By detecting a change in the amount of reflected or transmitted ionizing radiation, a water content measuring means for measuring the water content of the water-containing powder, and the weight of the water-containing powder sent to the conveying means. And a reaction management system for a water-containing powdery substance, which comprises means for calculating a predetermined reaction condition of the reaction based on the measured water content of the water-containing powdery substance.

Further, in the present invention, the water-containing powdery substance is preferably an unreacted reaction raw material recovered from the reaction solution, and the reaction raw material is represented by the formula (1):

[0012]

[Chemical 9]

(In the formula, R ¹ and R ² are each independently a halogen atom, a C1 to C8 alkyl group or a C2 to C8.
Represents an alkenyl group, and m and n are each independently 0.
Alternatively, it represents an integer of 1 to 4. More preferably, it is a diphenyl sulfone compound represented by

Further, in the present invention, it is preferable to use infrared rays, far infrared rays or near infrared rays as the ionizing radiation. Further, based on the water content of the measured water-containing powder, means for calculating the predetermined reaction conditions of the reaction,
It preferably has a function of calculating the amount of the reactant and / or solvent used in the reaction based on the measured water content of the water-containing powder, and the water content of the water-containing powder is 0. It is preferably in the range of 1% by weight to 30% by weight.

A second aspect of the present invention is an application of the first aspect of the present invention, wherein the formula (1)

[0016]

[Chemical 10]

(In the formula, R ¹ and R ² are each independently a halogen atom, a C1 to C8 alkyl group or a C2 to C8.
Represents an alkenyl group, and m and n are each independently 0.
Alternatively, it represents an integer of 1 to 4. ) In the presence of a base, a compound represented by the formula: R ³ —X ¹ (wherein
R ³ is, C1 to C8 alkyl group, C2-C8 alkenyl group, an aralkyl group which may have a C3~C8 cycloalkyl group or a substituent, ^{X 1} is a halogen atom. ) An alkyl halide represented by the formula: or a formula: X ² —R
⁴ -X ³ wherein, ^{R 4} is, C1 to which may have a substituent
C12 saturated or unsaturated hydrocarbon group, C1-C12 saturated or unsaturated hydrocarbon group having an ether bond, formula (3)

[0018]

[Chemical 11]

(In the formula, R ⁷ represents a methylene group or an ethylene group), or a formula (4)

[0020]

[Chemical 12]

(In the formula, R ⁸ is a hydrogen atom or C 1 to C ⁴
Represents an alkyl group. Represents a group represented ^{by), X 2,} X ³
Each independently represent a halogen atom. ] Formula (2) which has the process of adding the compound represented

[0022]

[Chemical 13]

{In the formula, R ¹ and R ² have the same meanings as described above, and Q represents a hydrogen atom, a C1-C8 alkyl group, C2-
C8 alkenyl group, C3-C8 cycloalkyl group, aralkyl group which may have a substituent, or formula (5)

[0024]

[Chemical 14]

[In the formula, X and Y are each independently
C1-C12 saturated or unsaturated hydrocarbon group which may have a substituent, C1-C12 saturated or unsaturated hydrocarbon group having an ether bond, formula (3)

[0026]

[Chemical 15]

(In the formula, R ⁷ represents a methylene group or an ethylene group), or a group represented by the formula (4)

[0028]

[Chemical 16]

(In the formula, R⁸Is a hydrogen atom or C1 to C4
Represents an alkyl group. ) Represents a group represented by. R^Three~ R⁶
Are each independently a halogen atom, C1-C8 al.
Represents a kill group or a C2-C8 alkenyl group, p, q, r
And t each independently represent 0 or an integer of 1 to 4.
However, a represents 0 or an integer of 1 to 10. ] A group represented by
Represents Production of diphenyl sulfone compound represented by
A method, comprising a water-containing powder of a compound represented by the above formula (1)
The ionizing radiation is irradiated to the object and the reflected or transmitted
By detecting a change in the amount of emitted radiation, the powder
Of measuring the water content of water and the water obtained by the measurement
In the formula (1) contained in the powder based on the content
A step of calculating the content of the compound represented, and the water-containing powder
Dissolve or suspend the substance in a solvent, and calculate the
Defined based on the content of the compound represented by the formula (1)
Amount of base and formula: R^Three-X¹(In the formula, R^ThreeAnd X
¹Represents the same meaning as described above. ) Alkyl hara represented by
Id or formula: X ^Two-R^Four-X^Three(In the formula, R^Four, X^TwoOver
And X^ThreeRepresents the same meaning as described above. ) The compound represented by
And a step of adding dipheni represented by the formula (2)
Provided is a method for producing a sulfone compound.

In the production method of the present invention, the hydrous powder of the compound represented by the formula (1) for measuring the water content is preferably a dehydrated cake recovered from the reaction solution. Further, by irradiating the water-containing powder of the compound represented by the formula (1) with ionizing radiation and detecting the change in the light amount of the reflected or transmitted ionizing radiation, the water content of the powder can be determined. It is preferable that the step of performing the measurement includes a step of irradiating the water-containing powdery substance, which is conveyed on the belt conveyor by a constant amount, with ionizing radiation.

Further, the water content of the water-containing powdery substance of the compound represented by the formula (1) whose water content is measured is
It is preferably 0.1% to 30% by weight. In the first and second inventions, as the ionizing radiation,
It is preferable to use infrared rays, far infrared rays, or near infrared rays.

[0032]

BEST MODE FOR CARRYING OUT THE INVENTION The reaction management system of the present invention comprises the steps of irradiating the surface of a water-containing powdery material, which is a reaction raw material, with ionizing radiation,
It has a means for measuring the water content contained in the water-containing powder by detecting the change in the amount of light reflected or transmitted by the ionizing radiation.

As the ionizing radiation used for the measurement, if the amount of water contained in the powdery substance can be measured by irradiating the surface of the powdery substance and detecting a change in the amount of light reflected or transmitted therethrough. There is no particular limitation. Examples of such ionizing radiation include visible rays, ultraviolet rays, infrared rays, near infrared rays, far infrared rays, and electron beams. Among these, in the present invention, it is preferable to use infrared rays, near infrared rays, or far infrared rays from the viewpoint of accurately measuring the water content.

To measure the water content of the powdery material, for example, the surface of the watery powdery material is irradiated with ionizing radiation and the change in the amount of reflected light or transmitted light is detected to determine the water content of the watery powdery material. It can be carried out using a device capable of measuring the content.

A conceptual diagram for measuring the water content of a water-containing powdery substance using this measuring apparatus is shown in FIG. In FIG. 1, the water-containing powdery substance 3 is continuously conveyed on the conveying means 2 by a constant amount. Here, the transporting means 2 is not particularly limited as long as it is a means capable of continuously transporting a certain amount of a water-containing powdery substance to a predetermined place (dissolution tank, reaction tank, etc.), but a belt conveyor is generally used. Target. Further, the automatic moisture meter 1 is installed above the conveying means 2 and irradiates the surface of the water-containing powdery substance 3 with ionizing radiation such as infrared rays and near infrared rays, and the amount of reflected light of the irradiated ionizing radiation. And a detection sensor 5 for detecting The detection sensor 5 detects the amount of reflected light, but a detection sensor that detects the amount of transmitted light may be used. Further, the irradiation unit 4 is
For example, the ionizing radiation having a wavelength that is difficult to be absorbed by moisture on the surface of the powdery substance and the wavelength of 2 to 4 which is absorbed by moisture.
Different types of ionizing radiation can be used, and the ionizing radiation of each of these wavelengths can be sequentially applied to the powder surface. Then, the detection sensor 5 detects the degree of absorption by the water as a change in the amount of reflected light (absorbance).

The automatic moisture meter 1 used has a relatively low water content (for example, a water content of 0% by weight) in order to improve the measurement accuracy of the water content of a water-containing powder.
By changing the wavelength of the ionizing radiation used for the measurement, in the case of 10% by weight) and in the case where the water content is relatively large (for example, in the case of the water content of 10% by weight to 30% by weight), It is preferable to have a function of reducing measurement error.

As a concrete example of the apparatus for measuring the water content,
JP-A-50-132887 and JP-A-61-494
No. 7, JP 61-29741, JP 61
-29742, JP-A-2-27227, JP-A-3-117750, JP-A-4-95856, JP-A-4-286938, and JP-A-4-28.
6939, JP-A-6-229918 and JP-A-6-229919, moisture content measuring devices, near infrared light moisture meter (trade name: OMM-300
0, manufactured by Literon) and the like.

Further, in the reaction management system of the present invention, the water-containing powdery substance is stored and sent out to the conveying means, and
It is preferable to further include a storage unit having a function (weight management function) capable of managing the weight of the water-containing powdery substance sent to the transportation unit. As such a storage means, for example, a water-containing powdery material is stored, and the water-containing powdery material is sent to a conveying means,
A storage hopper having a function of automatically stopping the carry-out at the time when a predetermined amount of the water-containing powdery substance is sent out is mentioned.

The reaction management system of the present invention is based on the measured water content and the content of the reaction raw material contained in the water-containing powder based on the weight of the water-containing powder sent to the conveying means, and the calculated reaction raw material. And a means for calculating reaction conditions based on the content of Here, the reaction conditions mean the amount of the reaction agent used to react with the reaction raw materials, the amount of the solvent, and the like. In addition to the reactant that directly reacts with the reaction raw material, the reactant includes a wide range of acids and bases, catalysts and the like.

The calculation of the water content and the reaction conditions can be carried out, for example, by a personal computer 10 including a data processing device 7, a memory unit 8 and a display 9 which interlock with the automatic moisture meter 1 as shown in FIG. .
The automatic moisture meter 1 and the personal computer 10 are linked via a controller 6, and the automatic moisture meter 1 and the controller 6, and the controller 6 and the personal computer 10 are removable. Although not shown, the automatic moisture meter 1 and the personal computer 10 can be connected without the controller 6.

When calculating the water content, the absorbance of a water-containing powder having a known water content is stored as basic data in the memory unit 8 in advance (in this case, a calibration curve is created based on the basic data). It is preferable to leave it). And
By comparing the absorbance of the water-containing powdery substance detected by the detection sensor 5 with the basic data (or the calibration curve), the measured water content of the water-containing powdery substance can be calculated. The reaction conditions include, in advance, the reaction conditions such as the molecular weight of the reaction raw material and the reactant, the reaction molar ratio, the amount of the solvent used per the reaction raw material (the reaction molar ratio, the amount of the solvent used per the reaction substance unit, etc.) in the memory unit 8. By inputting the basic data on the above, and using the basic data and the amount of the reactant contained in the water-containing powder obtained from the measured water content, the data processing device 7 automatically equipped with the calculation program. Can be calculated.
Further, these calculation results can be displayed on the display 9 in a predetermined format, or can be printed out from a printer (not shown).

Further, the present invention may be, for example, a system in which a moisture meter 1, a storage means 11 having a weight management function, and a personal computer 10 are connected to each other as shown in FIG. In this system, the personal computer 10 uses the measurement data of the absorbance from the moisture meter 1,
It is possible to receive the weight data of the hydrated powder sent from the storage tank 11 to the conveying means, and calculate the water content of the hydrated powder and the reaction conditions from these data. The calculation result can be output / displayed in a predetermined format.

The water-containing powder of the reaction raw material which is the object of the measurement of the water content of the present invention is not particularly limited as long as it is the water-containing powder of the reaction raw material (substrate) containing water. From the viewpoint of obtaining better measurement accuracy, the water content is preferably 0.1% by weight to 30% by weight. As such a water-containing powdery substance, a dehydrated cake which is a substance precipitated from water or a solution containing water and which is obtained by filtration is preferably exemplified. Further, the reaction raw material may be a reaction product obtained by the reaction (further used as the next reaction raw material) or an unreacted reaction raw material recovered after the completion of the reaction.

Among these, the reaction raw material is preferably a diphenyl sulfone compound represented by the above formula (1). Here, in the formula (1), R ¹ and R
² is each independently a halogen atom such as a fluorine, chlorine, bromine or iodine atom; C1 such as a methyl, ethyl, n-propyl, isopropyl, n-butyl or t-butyl group.
~ 8 alkyl group; represents a C2-8 alkenyl group such as propenyl, isopropenyl and butenyl groups. m and n each independently represent 0 or an integer of 1 to 4.

In the present invention, it is represented by the above formula (1).
4, among the dihydroxydiphenyl sulfone compounds
More preferred is 4'-dihydroxyphenyl sulfone.
To 4,4'-dihydroxydiphenyl sulfone,
In a water-immiscible solvent such as ruene, a predetermined amount of base and formula: R
^Three-X¹Or an alkyl halide represented by the formula: X^Two-R
^Four-X^ThreePredetermined amount in the reaction solution obtained by reacting the compound represented by
Of water is added to adjust the pH of the water layer and the desired product is taken out.
After the reaction, the crystals should be precipitated from the reaction solution and collected by filtration.
4'-dihydroxydiphenylsulfur recovered by
Hong dewatered cake is particularly preferred.

Next, the method for producing the diphenylsulfone compound represented by the above formula (2), which is an application of the reaction control method of the present invention, will be described in detail. In the production method of the present invention, first, a water-containing powdery substance of the dihydroxydiphenylsulfone compound represented by the above formula (1) as a reaction raw material, preferably a dehydrated cake recovered from the reaction solution is irradiated with ionizing radiation. Then, the moisture content of the powdery substance is measured by detecting the change in the light amount of the ionizing radiation reflected or transmitted.

Next, based on the calculated water content of the compound represented by the formula (1), the content of the compound represented by the formula (1), the solvent, the base, the formula: R ³ —X ¹ The amount of the alkyl halide represented by the formula, the compound represented by the formula: X ² —R ⁴ —X ³ or the like is calculated. Next, the water-containing powdery substance is dissolved or suspended in a predetermined amount of a solvent, and the base and the alkyl halide represented by the formula: R ³ —X ¹ or the formula: X are added thereto.
² -R ⁴ is reacted by adding a predetermined amount of the compound represented by -X ^3. According to the production method of the present invention, by grasping the amount of the net reaction raw material contained in the reaction recovered product by measuring the water content contained in the reaction recovered product, the amount of solvent, base amount, alkyl used in the reaction It is possible to calculate and manage the amount of preparations such as halides quickly and accurately.

In the alkyl halide represented by the formula: R ³ -X ¹ or the compound represented by the formula: X ² -R ⁴ -X ³ , R ³ is methyl, ethyl, n-propyl, isopropyl or n-. C1-C8 alkyl group such as butyl and t-butyl group; C2-C8 alkenyl group such as ethenyl, propenyl, isopropenyl, butenyl group; C3-C8 cycloalkyl group such as cyclopropyl, cyclopentyl, cyclohexyl group; or benzyl group Represents an aralkyl group which may have a substituent such as Among these, C2-C4 alkyl groups such as ethyl, n-propyl, isopropyl, n-butyl and t-butyl groups are preferable, and isopropyl group is particularly preferable.

R ⁴ is methylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, nonamethylene, decamethylene, undecamethylene, dodecamethylene, methylmethylene, dimethylmethylene, methylethylene, Methylene ethylene, ethyl ethylene, 1,2-dimethyl ethylene, 1-methyl trimethylene, 1-methyl tetramethylene, 1,3-dimethyl trimethylene, 1-ethyl-4-methyl-tetramethylene,

2-hydroxytrimethylene, 2-hydroxy-2-methyltrimethylene, 2-hydroxy-2-
C1-12 saturated carbonization which may have a substituent such as ethyltrimethylene, 2-hydroxy-2-propyltrimethylene, 2-hydroxy-2-isopropyltrimethylene, 2-hydroxy-2-butyltrimethylene group. Hydrogen radical;
C1-12 unsaturated hydrocarbon groups which may have a substituent such as vinylene, propenylene, 2-butenylene, ethynylene, 2-butynylene, 1-vinylethylene group; ethyleneoxyethylene, tetramethyleneoxytetramethylene, ethylene Oxyethyleneoxyethylene, ethyleneoxymethyleneoxyethylene, 1,3-dioxane-
C1 having ether bond such as 5,5-bismethylene group
~ A C12 saturated or unsaturated hydrocarbon group; represents either the group represented by the formula (3) or the group represented by the formula (4).

In the formula (3), R ⁷ represents a methylene group or an ethylene group, and in the formula (4), R ⁸ is a hydrogen atom;
Represents a C1-C4 alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl group; Here, R ^{3 to} R ⁶ are each independently a halogen atom such as fluorine, chlorine and bromine; methyl, ethyl and n.
-C1-C8 alkyl group such as propyl, isopropyl, n-butyl, t-butyl group; C2-C8 alkenyl group such as vinyl, propenyl, isopropenyl, butenyl group and the like. X ¹ , X ² and X ³ are the same or different and each represents a halogen atom. Examples of the halogen atom include a chlorine atom, a bromine atom and an iodine atom.

The base used is, for example,
Examples thereof include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkaline earth metal hydroxides such as magnesium hydroxide and calcium hydroxide; alkali metal carbonates such as calcium carbonate.

The production method of the present invention is carried out in the presence of a base, water,
Preference is given to carrying out either polar organic solvents or water-immiscible organic solvent bilayer systems. Examples of the water-miscible organic solvent include N, N-dimethylformamide, N, N-
Amide solvents such as dimethylacetamide, 1,3-dimethylimidazolidine, 1,3-dimethyl-2-imidazolidinone, N-methylpyrrolidone, hexamethylphosphoric triamide; tetrahydrofuran; acetone; dimethyl sulfoxide; Can be mentioned. Examples of the non-water-miscible organic solvent include aromatic hydrocarbon solvents such as benzene, toluene, chlorobenzene and dichlorobenzene;
Diethyl ketone, methyl isobutyl ketone (MIB
K), ketone solvents such as cyclohexanone; ester solvents such as ethyl acetate and propyl acetate; ether solvents such as diethyl ether and diisopropyl ether. The reaction temperature is usually in the range of -20 ° C to 150 ° C, preferably 30 ° C to 120 ° C, and the reaction is usually completed in several hours to tens of hours.

In the production method of the present invention, it is also possible to carry out the reaction by adding a newly prepared reaction raw material to the water-containing powdery substance which is the recovered reaction raw material. According to this method, by measuring the water content contained in the reaction recovered product and grasping the amount of the net reaction raw material contained in the reaction recovered product, the total of that amount and the amount of the reaction raw material newly supplied From the amount, the amount of solvent, the amount of base, the amount of alkyl halide, etc. used in the reaction can be calculated and managed quickly and accurately.

The diphenylsulfone compound represented by the above formula (2) can be obtained by the production method of the present invention. In formula (2), R ¹ , R ² , m and n have the same meanings as described above. Q is a hydrogen atom; C such as methyl, ethyl, n-propyl, isopropyl, n-butyl and t-butyl groups
1-8 alkyl group; C2-8 alkenyl group such as vinyl, propenyl, isopropenyl, butenyl group; C3-8 such as cyclopropyl, cyclopentyl, cyclohexyl group
Cycloalkyl group; benzyl, 4-chlorobenzyl, 2
An aralkyl group which may have a substituent such as a phenylethyl group; or a group represented by the above formula (5).

In the above formula (5), p, q, r and t each independently represent 0 or an integer of 1 to 4, and a is 1 to 1
Represents an integer of 10. X and Y are each independently methylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, nonamethylene, decamethylene, undecamethylene, dodecamethylene, methylmethylene, dimethylmethylene, methylethylene. , Methylene ethylene, ethyl ethylene, 1,2-dimethyl ethylene, 1-methyl trimethylene, 1-methyl tetramethylene, 1,3-dimethyl trimethylene, 1-ethyl-4-methyl-tetramethylene,

2-hydroxytrimethylene, 2-hydroxy-2-methyltrimethylene, 2-hydroxy-2-
C1-12 saturated carbonization which may have a substituent such as ethyltrimethylene, 2-hydroxy-2-propyltrimethylene, 2-hydroxy-2-isopropyltrimethylene, 2-hydroxy-2-butyltrimethylene group. Hydrogen radical;
C1-12 unsaturated hydrocarbon groups which may have a substituent such as vinylene, propenylene, 2-butenylene, ethynylene, 2-butynylene, 1-vinylethylene group; ethyleneoxyethylene, tetramethyleneoxytetramethylene, ethylene Oxyethyleneoxyethylene, ethyleneoxymethyleneoxyethylene, 1,3-dioxane-
C1 having ether bond such as 5,5-bismethylene group
To C12 saturated or unsaturated hydrocarbon group; represents either the group represented by the formula (3) or the group represented by the formula (4).

Specific examples of the compound represented by the formula (2) include 4-methoxy-4'-hydroxydiphenyl sulfone, 4-ethoxy-4'-hydroxydiphenyl sulfone and 4-n-propoxy-4'-hydroxy. Diphenyl sulfone, 4-isopropoxy-4'-hydroxydiphenyl sulfone, 4-n-butoxy-4'-hydroxydiphenyl sulfone, 4-sec-butoxy-4-hydroxydiphenyl sulfone, 4-t-butoxy-4'-
4-hydroxy-, such as hydroxydiphenyl sulfone
4'-substituted hydroxydiphenyl sulfone;

4- [4- (4-hydroxyphenylsulfonyl) phenoxy-4-butyloxy] -4 '-[4-
(4-Hydroxyphenylsulfonyl) phenoxy-3
-Propyloxy] diphenyl sulfone, 4,4'-bis [4- (4-hydroxyphenylsulfonyl) phenoxy-2-ethyloxy] diphenyl sulfone, 4,
4'-bis [4- (4-hydroxyphenylsulfonyl) phenoxy-3-propyloxy] diphenylsulfone, 4,4'-bis [4- (4-hydroxyphenylsulfonyl) phenoxy-4-butyloxy] diphenylsulfone, 4 , 4'-bis [4- (4-hydroxyphenylsulfonyl) phenoxy-5-pentyloxy]
Diphenyl sulfone, 4,4'-bis [4- (4-hydroxyphenylsulfonyl) phenoxy-6-hexyloxy] diphenyl sulfone, 4- [4- (4-hydroxyphenylsulfonyl) phenoxy-4-butyloxy] -4 ' -[4- (4-Hydroxyphenylsulfonyl) phenoxy-2-ethyloxy] diphenylsulfone, 4- [4- (4-hydroxyphenylsulfonyl) phenoxy-3-propyloxy] -4 '-[4- (4- Hydroxyphenylsulfonyl) phenoxy-2-ethyloxy] diphenyl sulfone, 4,4′-bis [4- [4
-(2-Hydroxyphenylsulfonyl) phenoxy]
Butyloxy] diphenyl sulfone, 4,4'-bis [4
-[2- (4-Hydroxyphenylsulfonyl) phenoxy] butyloxy] diphenyl sulfone, 1,1-bis
[4- (4-Hydroxyphenylsulfonyl) phenoxy] methane, 1,2-bis [4- (4-hydroxyphenylsulfonyl) phenoxy] ethane, 1,3-bis [4-
(4-Hydroxyphenylsulfonyl) phenoxy] propane, 1,4-bis [4- (4-hydroxyphenylsulfonyl) phenoxy] butane, 1,5-bis [4-
X in the formula (2) such as (4-hydroxyphenylsulfonyl) phenoxy] pentane and 1,6-bis [4- (4-hydroxyphenylsulfonyl) phenoxy] hexane.
And / or Y is a compound having a C1 to C12 saturated hydrocarbon group which may have a substituent;

1,2-bis [4- (4-hydroxyphenylsulfonyl) phenoxy] ethylene, 4,4'-bis [4- [4- (4-hydroxyphenylsulfonyl) phenoxy] -2-trans-butenyloxy] Diphenyl sulfone, 4- [4- [4- (4-hydroxyphenylsulfonyl) phenoxy] -2-trans-butenyloxy] -4 ′-[4- (4-hydroxyphenylsulfonyl) phenoxy-4-butyloxy] diphenyl sulfone, 4- [4- (4-hydroxyphenylsulfonyl)
Phenoxy-2-trans-butenyloxy] -4'-
[4- (4-hydroxyphenylsulfonyl) phenoxy-3-propyloxy] diphenyl sulfone, 4- [4
-[4- (4-Hydroxyphenylsulfonyl) phenoxy] -2-trans-butenyloxy] -4 '-[4-
(4-hydroxyphenylsulfonyl) phenoxy-2
-Ethyloxy] diphenyl sulfone, 1,4-bis [4
-[4- [4- (4-Hydroxyphenylsulfonyl) phenoxy-2-trans-butenyloxy] phenylsulfonyl] phenoxy] -cis-2-butene, 1,4-bis [4- [4- [4- (4 -Hydroxyphenylsulfonyl) phenoxy-2-trans-butenyloxy] phenylsulfonyl] phenoxy] -trans-2-butene and the like, in formula (2), X and / or Y are C1 to C12 which may have a substituent. A compound which is an unsaturated hydrocarbon group;

4,4'-bis [4- (4-hydroxyphenylsulfonyl) phenoxy] dibutyl ether,
2,2'-bis [4- (4-hydroxyphenylsulfonyl) phenoxy] diethyl ether, 4,4'-bis
[4- (4-hydroxyphenylsulfonyl) phenoxy-2-ethyleneoxyethoxy] diphenylsulfone, 2,2'-bis [4- [4- [4- (4-hydroxyphenylsulfonyl) phenoxy-2-ethyleneoxyethoxy] ] Phenylsulfonyl] phenoxy] diethyl ether, 2,4'-bis [2- (4-hydroxyphenylsulfonyl) phenoxy-2-ethyleneoxyethoxy] diphenylsulfone, 2,4'-bis [4- (2-hydroxyphenyl) Sulfonyl) phenoxy-2-ethyleneoxyethoxy] diphenyl sulfone, 4,4′-bis [3,5-dimethyl-4- (3,5-dimethyl-4-)
Hydroxyphenylsulfonyl) phenoxy-2-ethyleneoxyethoxy] diphenylsulfone, 4,4′-
In formula (2) such as bis [3-allyl-4- (3-allyl-4-hydroxyphenylsulfonyl) phenoxy-2-ethyleneoxyethoxy] diphenyl sulfone, C1 to C12 in which X and / or Y have an ether bond A compound which is a saturated or unsaturated hydrocarbon group of

Α, α'-bis [4- (4-hydroxyphenylsulfonyl) phenoxy] -p-xylene, α,
α'-bis [4- (4-hydroxyphenylsulfonyl) phenoxy] -m-xylene, α, α'-bis [4-
(4-Hydroxyphenylsulfonyl) phenoxy]-
o-xylene, α, α′-bis [4- [4- [4- (4-
Hydroxyphenylsulfonyl) phenyl-1,4-phenylenebismethyleneoxy] phenylsulfonyl] phenoxy] -p-xylene, α, α′-bis [4- [4- [4
-(4-hydroxyphenylsulfonyl) phenyl-
1,3-phenylenebismethyleneoxy] phenylsulfonyl] phenoxy] -m-xylene, α, α′-bis
[4- [4- [4- (4-hydroxyphenylsulfonyl) phenyl-1,2-phenylenebismethyleneoxy] phenylsulfonyl] phenoxy] -o-xylene,

4,4'-bis [4- (4-hydroxyphenylsulfonyl) phenyl-1,4-phenylenebismethyleneoxy] diphenylsulfone, 4,4'-bis
[4- (4-hydroxyphenylsulfonyl) phenyl-1,3-phenylenebismethyleneoxy] diphenylsulfone, 4,4′-bis [4- (4-hydroxyphenylsulfonyl) phenyl-1,2-phenylenebismethyleneoxy ] Diphenyl sulfone, 4,4'-bis
[3,5-Dimethyl-4- (3,5-dimethyl-4-hydroxyphenylsulfonyl) phenyl-1,4-phenylenebismethyleneoxy] diphenylsulfone, 4,
4'-bis [3,5-dimethyl-4- (3,5-dimethyl-4-hydroxyphenylsulfonyl) phenyl-
1,3-phenylene bismethyleneoxy] diphenyl sulfone, 4,4′-bis [3,5-dimethyl-4-
(3,5-Dimethyl-4-hydroxyphenylsulfonyl) phenyl-1,2-phenylene bismethyleneoxy] diphenyl sulfone, 4,4′-bis [3-allyl-
4- (3-allyl-4-hydroxyphenylsulfonyl) -1,4-phenylenebismethyleneoxy] diphenylsulfone, 4,4′-bis [3-allyl-4- (3
-Allyl-4-hydroxyphenylsulfonyl) -1,
3-phenylene bismethyleneoxy] diphenyl sulfone, 4,4′-bis [3-allyl-4- (3-allyl-
4-hydroxyphenylsulfonyl) -1,2-phenylenebismethyleneoxy] diphenylsulfone and the like, in the formula (2), a compound in which X and / or Y is a group represented by the formula (3);

4,4'-bis [4- (4-hydroxyphenylsulfonyl) phenoxy-2-hydroxypropyloxy] diphenyl sulfone, 1,3-bis [4- [4
In the formula (2) such as-[4- (4-hydroxyphenylsulfonyl) phenoxy-2-hydroxypropyloxy] phenylsulfonyl] phenoxy] -2-hydroxypropane, X and / or Y is represented by the formula (4). And a compound which is a group.

[0065]

EXAMPLES Next, the present invention will be described in more detail by way of examples. In the following examples, an online moisture meter (trade name: OMM-3000, manufactured by Literon) was used as an automatic moisture meter. This online moisture meter is a type that has a type of sensor that detects reflected light by using near-infrared rays having three types of wavelengths as irradiation light. Further, in the following Examples, 4,4′-dihydroxydiphenyl sulfone (hereinafter abbreviated as “BPS”) and bis (2-chloroethyl) ether were reacted with sodium hydroxide as a base in a water solvent. , Equation (6)

[0066]

[Chemical 17]

(Wherein a represents 0 or an integer of 1 to 10) is a reaction example.

First, as shown in FIG. 4, the dehydrated cake 3 (of BPS) obtained by filtering BPS precipitated from the reaction solution containing water with a centrifugal filter is stored in the storage hopper 11, and from there. It was conveyed to the dissolution tank 12 by the belt conveyor 2 in fixed amounts. At this time, the moisture content was measured using the online moisture meter 13 installed on the belt conveyor 2. The water content was determined by plotting a calibration curve using the measured value of BPS whose water content was previously measured as reference data and comparing this calibration curve with the actual measurement value. All of these calculations were performed using a predetermined calculation software installed in a personal computer (not shown in FIG. 4) linked with the online moisture meter 13. The water content of the dehydrated cake-like BPS at this time was 21.1% by weight.
Met. On the other hand, when a small amount of this dehydrated cake-like BPS was sampled to measure the water content, the water content was 20.9% by weight, and the difference from the value measured by the online moisture meter 13 was 0.2% by weight. Met.

Then, the measured value and the storage hopper 11
Calculate the weight of dehydrated cake-like BPS3 delivered from
The amounts of BPS and solvent charged to the dissolution tank 12 were calculated.
Further, the BPS solution dissolved in the solvent is transferred to a reaction tank (not shown), and the transferred BPS solution is further added with BPS.
(Prepared separately), based on the total amount of BPS content obtained from the water content measured by the automatic moisture meter and the newly added BPS, sodium hydroxide and bis (2-chloroethyl) ) The amount of ether added was calculated. These calculations are all done online with the Moisture Analyzer 13
It was performed using a personal computer linked to.
When the reaction was carried out by adding the calculated charged amounts, the reaction proceeded in the same manner as in the case where only dry BPS was used, and the target product was obtained in a similar yield.

From the above, by using the on-line moisture meter 13, the BPS reaction charge amount can be simply and quickly obtained with the measurement accuracy almost equal to the drying loss measurement by sampling (manual work) which has been performed conventionally. It turns out that automatic management is possible. Also, online moisture meter 1
It is possible to automatically calculate the charged amounts of the solvent used for the reaction, sodium hydroxide and bis (2-chloroethyl) ether, using a personal computer connected to No. 3, so in this embodiment using BPS as the reaction raw material. It was also found that total control of the example reactions is possible.

[0071]

As described above, according to the present invention,
The water content of the water-containing powder of the reaction raw material is measured using a simple, quick and accurate measuring method, and the water content contained in the water-containing powder of the reaction material, the reaction agent to react with the reaction raw material, etc. Provided is a reaction management system for hydrated powdery substances, which enables simple, quick and accurate calculation and management of the amount used. Further, according to the production method of the present invention, a production method capable of industrially (or in the production process) producing a diphenylsulfone compound by applying the reaction management system is provided.

[Brief description of drawings]

FIG. 1 is a conceptual diagram for measuring a water content of a water-containing powdery substance 3 conveyed on a conveying means 2 using a moisture meter 1.

FIG. 2 is a diagram showing measurement data of a light amount change (absorbance) of reflected light of ionizing radiation irradiated on the surface of a water-containing powdery substance 3 conveyed on a conveying means 2 from an automatic moisture meter 1 via a controller 6. FIG. 3 is a conceptual diagram of a system that transmits to the personal computer 10, calculates the water content and reaction conditions in the personal computer 10, and displays or outputs the calculation result.

FIG. 3 is data of the weight of the water-containing powdery substance 3 sent from the transporting device 2 and the amount of reflected light of ionizing radiation irradiated on the surface of the water-containing powdery substance 3 transported on the transporting device 2. FIG. 3 is a conceptual diagram of a system in which data of change (absorbance) is transmitted to the personal computer 10, the personal computer 10 calculates the water content of the water-containing powdery substance, the reaction condition, and the calculation result is displayed or output.

FIG. 4 is a graph showing the weight data of the dehydrated cake-like BPS 3 sent from the belt conveyor 2 and the dehydrated cake-like B conveyed on the belt conveyor 2 in the embodiment.
The data of the light quantity change (absorbance) of the reflected light of the ionizing radiation with which the surface of PS3 is irradiated is stored in the personal computer 10
FIG. 3 is a conceptual diagram of a system for transmitting the water content to the personal computer 10, calculating the water content of the water-containing powdery substance, the reaction condition, and displaying or outputting the calculation result.

[Explanation of symbols]

1 ... Automatic moisture meter 2 ... Conveying means (belt conveyor) 3: Water-containing powder 4 ... Ionizing radiation irradiation unit 5 ... Detection sensor 6 ... Controller 7 ... Data processing device 8 ... Memory section 9 ... Display 10 ... Personal computer 11 ... Storage means (storage hopper) 12 ... Dissolution tank 13 ... Online moisture meter

   ─────────────────────────────────────────────────── ─── Continued front page    F-term (reference) 2G059 AA01 AA05 BB09 CC09 DD12                       EE01 EE02 FF08 HH01 KK01                       MM05 MM10 MM12 PP04                 4H006 AA02 AC43 BE10 TA02 TB42                       TC32

Claims (12)

[Claims] 1. A reaction management system for controlling reaction conditions for reacting a water-containing powder material as a reaction raw material with a reaction agent, comprising irradiating the water-containing powder material with ionizing radiation and ionizing the reflected or transmitted ionization radiation. By detecting the change in the amount of radiation,
Means for measuring the water content of the water-containing powder, and means for calculating the predetermined reaction conditions of the reaction, based on the weight of the water-containing powder and the water content of which the water content was measured. A reaction management system for water-containing powdery substances. 2. A reaction management system for controlling reaction conditions for reacting a water-containing powdery substance as a reaction raw material with a reaction agent, comprising a storage means for storing the water-containing powdery substance and delivering a predetermined amount thereof to a conveying means. , A transporting means for transporting the water-containing powdery substance sent from the storage tank, and irradiating the water-containing powdery substance with ionizing radiation in the process of transporting the water-containing powdery substance, and the reflected or transmitted ionizing radiation By detecting the change in the amount of light, the water content measuring means for measuring the water content of the water-containing powder, and the weight of the water-containing powder sent to the conveying means and the measured water-containing powder And a means for calculating a predetermined reaction condition of the reaction based on the water content of the reaction management system for a water-containing powdery substance. 3. The reaction management system according to claim 1, wherein the water-containing powder is an unreacted reaction raw material recovered from the reaction solution. 4. The reaction raw material is represented by the formula (1): (In the formula, R ¹ and R ² each independently represent a halogen atom, a C1 to C8 alkyl group or a C2 to C8 alkenyl group, and m and n each independently represent 0 or an integer of 1 to 4. The reaction management system according to any one of claims 1 to 3, which is a diphenyl sulfone compound represented by the formula (1). 5. The reaction management system for a water-containing powdery substance according to claim 1, wherein infrared rays, far infrared rays or near infrared rays are used as the ionizing radiation. 6. A means for calculating a predetermined reaction condition of the reaction based on the measured water content of the water-containing powdery substance,
The water-containing powder according to any one of claims 1 to 5, which has a function of calculating the amount of the reactant and / or solvent used in the reaction based on the measured water content of the water-containing powder. Reaction management system. 7. The water-containing powdery substance reaction management system according to claim 1, wherein the water-containing powdery substance has a water content of 0.1% by weight to 30% by weight. 8. A formula (1): (Wherein R ¹ , R ² m and n have the same meanings as described above), in the presence of a base, the formula: R ³ —X ¹ (wherein R ³ is An alkyl halide represented by a C1 to C8 alkyl group, a C2 to C8 alkenyl group, a C3 to C8 cycloalkyl group or an aralkyl group which may have a substituent, and X ¹ represents a halogen atom, or a formula. : ^X 2 ^-R 4 -X ³ wherein, ^{R 4} is,
A C1 to C12 saturated or unsaturated hydrocarbon group which may have a substituent, a C1 to C12 saturated or unsaturated hydrocarbon group having an ether bond, a compound represented by the formula (3): (In the formula, R ⁷ represents a methylene group or an ethylene group.)
Or a group represented by the formula (4): (In the formula, R ⁸ represents a hydrogen atom or a C1 to C4 alkyl group.), And X ² and X ³ each independently represent a halogen atom. ] Formula (2) with the step of adding the compound represented {In the formula, R ¹ and R ² have the same meanings as described above, and Q is
A hydrogen atom, a C1-8 alkyl group, a C2-8 alkenyl group, a C3-8 cycloalkyl group, an aralkyl group which may have a substituent, or a compound represented by the formula (5): [In the formula, X and Y are each independently a C1-C12 saturated or unsaturated hydrocarbon group which may have a substituent, a C1-C12 saturated or unsaturated hydrocarbon group having an ether bond. A group of formula (3): (In the formula, R ⁷ represents a methylene group or an ethylene group.)
Or a group represented by the formula (4): (In formula, R < ⁸ > represents a hydrogen atom or a C1-C4 alkyl group.). R ^{3 to} R ⁶ are each independently a halogen atom, a C 1 to C 8 alkyl group or C
It represents a 2-C8 alkenyl group, p, q, r, and t each independently represent an integer of 0 or 1 to 4, and a represents an integer of 0 or 1 to 10. ] Represents the group represented by. A method for producing a diphenylsulfone compound represented by the following formula, wherein a water-containing powdery substance of the compound represented by the formula (1) is irradiated with ionizing radiation, and a change in the amount of light of the ionizing radiation reflected or transmitted is detected. By doing so, the step of measuring the water content of the powder, and the content of the compound represented by the formula (1) contained in the powder based on the water content obtained by the measurement. A step of calculating, and dissolving or suspending the water-containing powder in a solvent, there,
An amount of a base determined based on the calculated content of the compound represented by the formula (1), and a formula: R ³ —X ¹ (wherein,
R ³ and X ¹ have the same meanings as described above. ) Or an alkyl halide represented by the formula: X ² —R ⁴ —X ³ (wherein R
⁴ , X ² and X ³ have the same meanings as described above. ) And a step of adding the compound represented by the formula (2). 9. The water-containing powdery substance of the compound represented by formula (1) for measuring the water content is dehydrated cake recovered from the reaction solution, and is represented by formula (2). A method for producing a diphenyl sulfone compound. 10. The water content of the powdery substance is obtained by irradiating a water-containing powdery substance of the compound represented by the formula (1) with ionizing radiation and detecting a change in the amount of the ionizing radiation reflected or transmitted therethrough. The diphenyl sulfone represented by the formula (2) according to claim 8 or 9, wherein the step of measuring the content includes a step of irradiating a water-containing powdery substance conveyed on a belt conveyor by a constant amount with ionizing radiation. Method for producing compound. 11. The method for producing a diphenylsulfone compound represented by the formula (2) according to claim 8, wherein infrared rays, far infrared rays, or near infrared rays are used as the ionizing radiation. 12. The water content of the water-containing powdery substance of the compound represented by the formula (1), wherein the water content is measured, is 0.1% by weight to 30% by weight. A method for producing a diphenylsulfone compound represented by the formula (2) according to any one of claims.