JPS6253957A - Production of bisphenol s derivative - Google Patents

Abstract

PURPOSE:To obtain a compound useful as a developer for thermographic recording paper and capable of preventing the ground fog in good yield, by subjecting 4,4'-diallyloxydiphenyl sulfone to Claisen rearrangement in a specific solvent. CONSTITUTION:The amount of 3-allyl-4-hydroxy-4'-allyloxydiphenyl sulfone which is a mono-rearrangement product obtained by rearranging only one of 4,4'-diallyloxydiphenyl sulfone is adjusted to 5-20% based on the weight of the raw material 4,4'-diallyloxydiphenyl sulfone, and the formation of 3,3'- diallyloxy-4-4'-dihydroxydiphenyl sulfone which is a di-rearrangement product is suppressed to <=90% to carry not reaction, and 3,3'-diallyl-4,4'- dihydroxydiphenyl sulfone is obtained, recrystallized and purified in a mixed solvent of three of a dichloroalkane, aromatic and alcoholic solvents to give the aimed substance.

Description

Detailed Description of the Invention [Industrial Application Field] The present invention relates to the production of 3,37-diallyl-4,4'-dihydroxydiphenyl sulfone, which is used as a color developer for thermal recording paper that prevents background capri. It is about the method. Generally, heat-sensitive recording materials are prepared by preparing a coating liquid by mixing in advance a fine dispersion of a colorless or light-colored leuco dye and a fine dispersion of a color developer, which is a phenolic compound, and applying this coating liquid to paper, etc. Manufactured by coating and drying. If the coating liquid and heat-sensitive recording material develop color before use, they will not be able to achieve their purpose, and even if the color development is light, the commercial value as a heat-sensitive recording material will decrease. It is preferable that it be as colorless as possible. Generally, if the color developer contains many impurities, the coating liquid develops color and the heat-sensitive recording material develops color, resulting in so-called capri. When using 3゜3'-sialyl-4,4'-dihydroxydiphenylsulfone as a color developer,
If the reaction product is used as it is, the above-mentioned color development occurs and it is not practical at all. The present invention relates to a production method including a rearrangement method and a subsequent purification method for obtaining 3,3'-diallyl-4,4'-dihydroxydiphenyl sulfone with very little color development or capri.

[Conventional technology]

Various allyl aryl ethers
・th@re) undergoes ortho-rearrangement in yields of several to 85 or more when reacted at 160 to 280°C for several minutes to over ten hours without a solvent or in the presence of a solvent such as kerosene or dialkylaniline. There is a report that (0RGANIC
REACTIONS, Vo 1 ume n,
IIP, 1-48).

There are also reports that use catalysts to cause rearrangements at low temperatures (C) IEMISTRY LETTER 8, PP
-1041~1044, 1975 Publiahe
d by the Chemi-cal 5oclet
y of Japan) 64.4'-Diallyloxydiphenyl sulfone also becomes soluble in aqueous caustic soda solution when reacted at 190 to 230°C for 4 to 8 hours, and Claisen rearrangement occurs to form phenolic OH. The product was approved. In the reaction mixture of Claisen rearrangement of 4,4'-diallyloxydiphenylsulfone,
unreacted 4,4'-diallyloxydiphenyl sulfone,
3-allyl-4-hydroxy-4' with only one rearrangement
- In addition to allyloxydiphenylsulfone and the target product 3,3'-diallyl-4,4'-dihydroxy-diphenylsulfone, cyclization occurs between the OH group of the rearranged product and the ortho allyl group. By-products of furan compounds such as five-membered ring coumaran type and six-membered ring chroman type, as well as other by-products considered to be highly polar substances, were also confirmed by IIPLC (liquid chromatography) analysis. .

- As an example, 4,4'-diallyloxydiphenylsulfone was prepared without solvent at 200-210°C under a N2 stream.
As a result of HPLC analysis, the time-rearranged product contained about 0.05% of unreacted raw material and about 5% of 3-allyl-4-hydroxy-4'-allyloxydiphenylsulfone, a mono-rearranged product.
In addition to approximately 90% of 3,3'-diallyl-4,4'-dihydroxydiphenylsulfone, which is a di-rearranged product, several other peaks were observed, including bisphenol S and bisphenol S, which are more polar. It was observed that even substances were being produced. As described above, the rearrangement product as it is contains many by-products, and the aforementioned coating liquid itself develops a strong color, making it impractical as a color developer for heat-sensitive recording paper.

[Problem that the invention seeks to solve]

As a result of various studies to eliminate this coloring of the coating liquid, it was found that there is a possibility of eliminating this coloration by using a recrystallization method.

However, lower alcohols such as methanol and ethanol, which are usually used as recrystallization solvents, as well as dioxane, tetrahydrofuran, dimethylformamide, dimethyl sulfoxide, and various ketones, have too high a solubility and the yield of crystals is extremely poor. In order to reduce the solubility, water was added to these solvents, but the solution only separated into an oil that required several hours for crystallization or did not crystallize at all.

Esters such as ethyl formate and methyl acetate can be crystallized, but it is difficult to obtain a good yield. Dicarboxylic acid esters such as ethyl oxalate and ethyl malonate are relatively good solvents, but they have the disadvantage of high boiling points.
It is disadvantageous industrially. Ethane dichloride (1,2-dichloroethane) is a good solvent, but the capri was still quite strong in the second recrystallization, and it was necessary to repeat the recrystallization several times to eliminate the capri. Then, in the case of the second and third recrystallization, the solubility decreased considerably, and it was necessary to use 10 to 30 times the amount of dichloroethane. Even if the amount of ethane dichloride used is increased to about 10 times the amount of ethane dichloride used, and a portion of lower alcohol such as methanol or propatool is used in combination with 1 to 2% of the amount of ethane dichloride, it will dissolve, but the yield will decrease. In addition, aromatic solvents have extremely low solubility and are not practical.

In the case of aromatic solvents with high boiling points, such as dichlorobenzene, the reaction product can melt and dissolve in the solvent at high temperatures, but upon cooling, it separates into an oil and then solidifies. No refining effect can be obtained.

[Means for solving problems]

The Claisen rearrangement reaction can be carried out in either a solvent-free or solvent-based manner, but avoid solvent-free rearrangement reactions in which temperature control is difficult and the reaction is treated as a solid when cold, and reactions in which ethylene glycol is used as a solvent, which produce highly polar substances, as much as possible. It is preferable to perform the rearrangement reaction in the presence of a mineral oil-based solvent whose boiling point is adjusted to 180-270°C, suppress the formation of di-rearranged products to 90% or less, and prevent the increase of the capri component as much as possible during the reaction process. In addition, the present inventors have determined that the resulting reaction product is
1. By a purification method of recrystallization using a tri-compound solvent consisting of a small amount of a dichloroalkane such as 2-dichloroethane, an aromatic solvent such as toluene, and a solvent with extremely high solubility such as isoglono-9ol, 3,3'-diallyl-4 with improved yield and little or no capri
, 4'-dihydroxydiphenyl sulfone can be obtained, leading to the present invention.

According to the present invention, there is provided a method for producing 3°3'-diallyl-4,4'-dihydroxydiphenyl by subjecting 4,4'-diallyloxynophenyl sulfone to Claisen rearrangement. Method C: 3-allyl-4-hydroxy-4'- which is a mono-rearranged product in which only one side of 4,4/-diallyloxydiphenylsulfone is rearranged.
The amount of allyloxydiphenyl sulfone was adjusted to 4.4% of the raw material.
The amount is 5 to 20% based on the weight of '-diallyloxydiphenylsulfone, and the reaction is carried out by suppressing the formation of 3,3'-diallyl-4,4'-dihydroxydiphenylsulfone, which is a di-rearranged product, to 90% or less. It is characterized by terminating.

According to the present invention, there is also 3 obtained by the above method,
A reaction product containing 3'-diallyl-4,4'-dihydroxydiphenylsulfone as a main component is treated with c) at least one dichloroalkane solvent as a recrystallization solvent, and (B)
) at least one aromatic solvent and (C) at least one alcohol-based or (and) glycol-based or (and) ether-based solvent, each of 10 to 90% by weight;
10~9o! A method for producing 3゜3'-diallyl-4,4'-dihydroxydiphenylsulfone, characterized by recrystallizing and purifying it using a mixed solvent in an amount of 0.1 to 301i. is provided.

In the present invention, 1,2-
In addition to dichloroethane, 1,3-dichloroguronone, 1
, 4-dichlorobutane, etc. can be used. Also,
As the aromatic solvent, in addition to toluene, benzene, xylene, monochlorobenzene, dichlorobenzene, trichlorobenzene, monochlorotoluene, nochlorotoluene, etc. can be used. In addition to impropagol, methanol, ethanol, furopanol, butanol, ethylene glycol, diethylene glycol, dioxane, tetrahydrofuran, dimethylformamide, dimethyl sulfoxide, acetone, methyl ethyl ketone, diethyl ketone, etc. are used as solvents with high solubility. be able to.

In addition, in order to avoid handling the rearrangement product as a solid, first make it into an alkaline aqueous solution, add a solvent such as ethane dichloride, which is a component of the recrystallization solvent, and then make it acidic by adding an aqueous solution of hydrochloric acid, etc. Alternatively, after dissolution, the solution may be separated into layers using an apparatus, and after removing the saline solution, the remaining residue may be recrystallized by adding toluene or alcohol as a recrystallization solvent. Furthermore, alcohols that are hardly soluble in an aqueous inorganic salt solution when dichloroethanes and toluenes coexist,
Regarding ketones, even if alcohols are added together with dichloroethanes and toluenes before separating and removing the inorganic salt aqueous solution, there is no problem since the alcohols will not be removed together with the aqueous solution.

For convenience of operation, the recrystallization solvents may be added separately in stages. It is sufficient that the entire amount is added by the time of cooling recrystallization.

〔Effect of the invention〕

4,4'-sialyloxydiphenylsulfone undergoes Claisen rearrangement to form 3,3'-diallyl-4゜4'-
When producing a color developer for heat-sensitive recording materials containing dihydroxydiphenyl sulfone as a main component, by carrying out the production method of the present invention, a coating liquid that is a mixture of a fine dispersion of a leuco dye and a fine dispersion of a color developer can be produced. It becomes possible to produce a color developer with very little or no color development and fog on heat-sensitive recording materials at a high yield and through simple operations. In addition, depending on the quality of the rearranged product and the purpose of the product, the yield can be further increased at the expense of some capri by adjusting the amount of lower alcohols such as isopropanol. On the other hand, it is possible to obtain a color developer completely free of capri, at the cost of lower yield. Furthermore, by carrying out the present invention, manufacturing costs and performance can be adjusted as desired.

〔Example〕

The invention will be further explained below by way of examples.

Performance test method (color development of paint liquid, capri test) In order to evaluate the cloth effect, a paint liquid was prepared and evaluated as follows.

Each 'ri product 0.0! Put M in a mortar and add 5 PV to it.
A aqueous solution 1. Add Of, crush thoroughly with a pestle, add 3 parts of water, and add
2 was added and further pulverized. This liquid was put into a test tube with an inner diameter of 10 mm and a length of 120 mm, and then 3 drops of a fine dispersion of leuco dye (approximately 0.19 F) having the following composition were added dropwise, and the temperature was 50 to 55℃ while stirring with a snow cuff. After warming for 5 minutes in a hot bath, leave it at room temperature for 120 minutes or more, and then check the brightness scale (
Japan Dyeing Research Institute Foundation! The brightness of the paint liquid was determined by visually checking the brightness of the paint liquid. Note that the brightness of the blank (without developer) was N=8. If N = 7.5 or more, it can be considered that there is almost no fog.

Leuco dye dispersion composition 3-N-methyl-N-cyclohexylamino-6-methyl-7-anilinofluorane...1.5t10
% PVA aqueous solution ・2.0 water
...0.5 (stock solution sufficiently finely dispersed in a sand mill 4.0) The above finely dispersed stock solution 4
．． Of water 8. The mixture was diluted with Of to obtain a fine leuco dye dispersion.

Example 1 4,4'-diallyloxydiphenyl sulfone (purity 99.9% by HPLC analysis) was placed in a 1000d four-way flask.
0chi) 330t (1.0 mol), MCC Oil-8 (manufactured by Idemitsu Kosan) 220t, white kerosene (manufactured by Daikyo Oil) 220
After replacing with N2, heat at 200-210℃ under N2 gas flow.
The mixture was rearranged for 5 hours. This product was allowed to stand for a while, and the reaction product separated into the lower layer was pipetted with about 3 f. to prepare a separate sample for analysis. The HPLC analysis results showed that the unreacted raw material contained 19.8% mono-translocated product and 77.4% di-transposed product.
%Met.

16.5 f of ethylene glycol was added to the sampled product at 150°C with stirring, and an aqueous solution of 82.5 f (2.0 mol) of caustic soda and 495 tons of water was gradually added to the sample at 125°C. In addition, an alkaline aqueous solution of the reaction product was prepared, and after the mixture was allowed to stand still, the alkali aqueous solution in the lower layer was extracted, leaving the paraffin oil in the upper layer. The amount of this alkaline aqueous solution was 905f.

A portion of this alkaline aqueous solution 225f (0.2-5 mol)
was placed in a 500-meter flask, dichloroethane (1,2-dichloroethane) sof was added, and the mixture was stirred for 20 minutes.
Gradually add 97r (0.53 mol) of dihydrochloric acid aqueous solution to make it acidic, and after stirring for a while at about 75°C, let it stand to separate into layers.The upper layer of inorganic salt aqueous solution is removed. After adding 8.4 f of nol and stirring and dissolving at 80 to 85° C. for a while, the mixture was cooled and recrystallized. After filtration at 25°C, the crystals were washed with a mixture of 40 g of ethane dichloride and 40 f of toluene, and then washed with 100 g of water.
Dry.

Discharge amount 50.8 liters (61.6 liters) Brightness of paint liquid N=8 Example 2 225 f of the remaining alkaline aqueous solution obtained in Example 1 (0.2 liters)
Recrystallization was carried out in the same manner as in Example 1, except that 5 mol) was used and the inproper tool was 4.2 t.

Gain! k 67,jl (81,7ch) Lightness of paint liquid N=7 Example 3 The reaction was carried out in the same manner as in Example 1 except that the reaction time was changed to 6 hours in Example 1 to obtain an alkaline aqueous solution. . HPLC
Analysis results show 0.51% of unreacted raw material and 14.0 mono-translocated product.
%, and the di-translocation product was 82.1%.

Subsequently, recrystallization was performed in the same manner as in Example 1.

Amount obtained: 53.6 r (65,0 chi) mp
14 B, 5-152.0℃ Brightness of paint liquid
N=8 to 8.5 Example 4 225 f (0,2
Recrystallization was carried out in the same manner as in Example 1, except that the amount of isoglono and nol was changed to 4.2 t.

Amount obtained: 66.1 (81,0chi) alp
148.7-152.2℃ Brightness of paint liquid N
F ~ 7.5° Comparative Example 1 225f (0,2
Recrystallization was carried out in the same manner as in Example 1, except that 5 mol) was used and isopropanol was not used.

Amount obtained: 75.9f (92chi) Brightness of paint liquid N = 4.5~5 (Capri is terrible)
Example 5 A reaction was carried out in the same manner as in Example 1 except that the reaction time was changed to 7 hours to obtain an alkaline aqueous solution. HPLC
The analysis results are: 0.44% of unreacted raw material, 8.2% of mono-rearranged product.
%, and the di-translocation product was 88.1%.

Subsequently, recrystallization was performed in the same manner as in Example 1.

Amount obtained: 48.7F (59.0ch) Brightness of paint liquid N=8 Example 6 225 t (0.25t) of the alkaline aqueous solution obtained in Example 5
Recrystallization was carried out in the same manner as in Example 1, except that the amount of isopropanol was changed to 4.2 f.

-[68,5F (83,0%) Brightness of paint liquid N=6 Comparative Example 2 Except for not using isopropanol in Example 6,
Recrystallization was carried out in the same manner as in Example 1.

Amount obtained: 74.3f (90.0chi) Brightness of paint liquid N = 4.5-5 (severe fog) Example 7 Same as Example 1 except that the reaction time was 8 hours. The reaction was carried out to obtain an alkaline aqueous solution. HPLC
The analysis results are 0.20% of unreacted raw material and 7.0% of mono-rearranged product.
The number of di-translocation products was 88.7.

Subsequently, recrystallization was performed in the same manner as in Example 1.

Brightness of paint liquid N = 6.5 Example 8 A 225f (0,2%) alkaline aqueous solution of the residue obtained in Example 7
Recrystallization was carried out in the same manner as in Example 1, except that the isopropanol was changed to 11 and Or.

Gain! Brightness of 42.0f (50.9%) paint liquid N=7-7.5 Comparative Example 3 225r (0.25 mol) of the alkaline aqueous solution obtained in Example 3 was added to 1o00+++A! Place the mixture in a Yotsuro flask, add 300 t of ethane dichloride, and while stirring, gradually add 20% aqueous hydrochloric acid solution 97F (0.54 mol) to make it acidic.
After stirring for a while at .degree. C., the mixture was allowed to separate into layers, the upper aqueous layer was extracted, and the remaining lower layer was cooled and recrystallized. It was filtered at 25°C, washed with 100f of water, and then dried.

Amount obtained: 46.2f (56.0%) Brightness of paint liquid: N=4.5 (bad Capri) Comparative Example 4 °Crystals 3B and Ot obtained in Comparative Example 3 above were mixed with dichloroethane 3
It was dissolved in a mixed solvent of 80f and 3.8t of methanol, cooled, and recrystallized. The crystals were filtered, washed with 50 g of ethane dichloride, and dried.

Example 9 The reaction was carried out in the same manner as in Example 1, except that white kerosene was not used in Example 1, MC Oil WS (Idemitsu Kosan) 440r was used, and the reaction was carried out for 4.5 hours. It was made into an aqueous solution. The HPLC analysis results showed that the unreacted raw material was 0.62%, the mono-rearranged product was 12.5%, and the di-rearranged product was 83.1%.

Subsequently, recrystallization was performed in the same manner as in Example 1.

Obtained i 47.7F (57.8%) Brightness of paint liquid N = 7.5 Example 1O The remaining alkaline aqueous solution obtained in Example 9 2252 (0.2
Recrystallization was carried out in the same manner as in Example 1, except that inglono-9-nol was changed to 4.2 f using 5 mol).

Amount obtained: 67.0F (81.2%) Brightness of coating liquid: N=6 Example 11 Example 9 except that the reaction time was 5.5 hours in Example 9.
The reaction was carried out in the same manner as above to obtain an alkaline aqueous solution. H.P.L.
C analysis results are 0.48% of unreacted raw material, 10 mono-rearranged products.
．． 5%, and 85.5 di-translocation products.

Subsequently, recrystallization was performed in the same manner as in Example 1.

Amount obtained: 47.8 f (57.9 t) Brightness of paint liquid N = 7 Comparative Example 5 4,4'-diallyloxydiphenyl sulfone (HPLC analysis purity 99.0 t) was placed in a 1000-fourth flask.
Add 30F (1.0 mol) and 600r of ethylene glycol, and after replacing with N2, at 195-200°C under a N2 stream.
The reaction took place for 5.5 hours. After the reaction, pour it into water and crush it.
Washed with water. After drying, displacement 320t1 yield 97.0'%
Met. mp134.5-145.5°C.

The HPLC analysis results showed that the unreacted raw material was 0.24 J, the mono-rearranged product was 8.42%, and the di-rearranged product was 81.0 J.

Continue with powder 80. 90thiacetic acid 160f1 using Of
It was recrystallized from a mixed solvent of 160F water, filtered, washed, and dried. Displacement: 66.0f (82.5 inches) (Total yield: 80.
0%) mp142-147°C. Brightness of paint liquid N〈4 (Very high Capri) Comparative Example 6 Crystals obtained in Comparative Example 6 60. Recrystallize from a mixed solvent of 150 F of ethane dichloride and 1.52 F of water using Or, filter,
Washed and dried.

Brightness of paint liquid N=5 (bad Capri) Comparative Example 7 Crystals obtained in Comparative Example 6 37. Of, 400f of ethane dichloride, 3.0f of methanol. The product was recrystallized from a mixed solvent of or, filtered, washed, and dried.

mp 148-152℃ Procedural amendment (voluntary) July 7, 1985 Michibe Uga, Commissioner of the Patent Office 1, Indication of the case 1985 Patent Application No. 191972 2, Name of the invention Manufacture of bisphenol S derivatives Method 3, Relationship with the case of the person making the amendment Patent applicant name: NICCA CHEMICAL INDUSTRY CO., LTD. 4, Agent address: 5-8-10 Toranomon-chome, Minato-ku, Tokyo 105
Column 6 of "Detailed Description of the Invention" of the specification to be amended, contents of the amendment (a) Page 19 of the specification, line 9, "filtered, and further" was replaced with "filtered, and added to 80 g of ethane dichloride." Clean it, and then adjust it to J.

(Al Page 21 of the specification, 3rd to 4th lines from the bottom, "filter, wash," replaces "filter, 50 g of 90% acetic acid, 50 g of water,
Wash with 0g of mixed solution and correct it to ``.

(8) On page 22, line 2 of the details, the text "Comparative Example 6" will be amended to "Comparative Example 5."

(Jin) On page 22 of the specification, line 4, "filter, wash, J" will be corrected to "filter and wash with 80 g of dichloroethane."

(・t) Page 22 of the specification, line 10, “filtration, washing,”
It says, ``Filter, add 40g of dichloroethane and 0 methanol.
．． Wash with 3g of mixed solution and correct to j.

Procedural amendment (voluntary) December 17, 1985 Director General of the Patent Office Kadobe 1, Indication of the case 1985 Patent Application No. 191972 2, Name of the invention Process for manufacturing color developer for thermal recording paper (New name) 3. Relationship with the case of the person making the amendment Patent applicant name: NICCA CHEMICAL CO., LTD. 4. Agent (4 others) 5. Subject of amendment (1) Change in the “title of the invention” in the specification Column (2) “Claims” column of the specification (3) Column 6 of “Detailed Description of the Invention” of the specification, contents of amendment (2. Scope of Claims column) I will correct it.

(3) A. On page 3, line 5 of the specification, the phrase "method for producing sulfone" will be amended to "method for producing r-sulfone color developer."

mouth, page 4, line 3 of the specification, "for obtaining sulfone"
Correct the statement to "for obtaining a color developer consisting of sulfone."

C. On page 6, line 17 of the specification, the phrase "extremely poor solubility" will be amended to "extremely poor solubility, which has the disadvantage that it cannot be put to practical use. Also, the solubility is extremely poor."

2. On page 9, lines 3 and 4 of the specification, the phrase ``manufacturing diphenyl'' will be corrected to ``manufacturing a color developer for thermal recording paper made of diphenyl.''

Ho, E! Page 9, lines 12 to 15 of Part A, - The phrase “A reaction was obtained” was amended to “The reaction was completed and a reaction was obtained.” Masu.

, page 10 of the specification, lines 3 to 5, “Characterized by...
・・・・・・・・・Provided. ” is ``Characteristics.

” will be corrected.

7. Claims amended list of attached documents 1 copy 2. Claim 1: Claisen rearrangement of 4,4-diallyloxydiphenyl sulfone to produce 3,3'-diallyl-4,4'-
In producing a color developer for thermal recording paper consisting of dihydroxydiphenylsulfone, 3-allyl-4-hydroxy-41-, which is a mono-rearranged product in which only one side of 4,4'-diallyloxydiphenylsulfone is rearranged, is used. The weight of allyloxydiphenylsulfone is 5 to 20% based on the weight of the raw material 4,4'-diallyloxydiphenylsulfone.
%, and the di-translocation product a, a? -diallyl-4,4'
- The reaction was terminated by suppressing the production of dihydroxydiphenyl sulfone to 90% or less, and the resulting 3,3
A reaction product containing ′-diallyl-4゜4′-dihydroxydiphenylsulfone as a recrystallization solvent (
A) at least 11 st of dichloroalkane solvent, and (
3) At least one kind of aromatic solvent and at least 1 m of an alcohol-based or (and) glycol-based or (and) ether-based solvent are each mixed at 10 to 90 parts by weight and 1 part by weight.
A method for producing a color developer for thermal recording paper, which comprises recrystallizing and purifying the color developer using a mixed solvent in an amount of 0 to 90% by weight and 0.1 to 30% by weight.

Claims (1)

[Claims] In producing 3,3'-diallyl-4,4'-dihydroxydiphenyl sulfone by Claisen rearrangement of 1,4,4'-diallyloxydiphenyl sulfone, 4,
The amount of 3-allyl-4-hydroxy-4'-allyloxydiphenylsulfone, which is a mono-rearranged product in which only one side of 4'-diallyloxydiphenylsulfone is rearranged, is determined by the weight of the raw material 4,4'-diallyloxydiphenylsulfone. 3,3′- which is a di-translocation product.
A method for producing 3,3'-diallyl-4,4'-dihydroxydiphenyl sulfone, which comprises terminating the reaction by suppressing the production of diallyl-4,4'-dihydroxydiphenyl sulfone to 90% or less. In producing 3,3'-diallyl-4,4'-dihydroxydiphenyl sulfone by Claisen rearrangement of 2,4,4'-diallyloxydiphenyl sulfone, 4,
The amount of 3-allyl-4-hydroxy-4'-allyloxydiphenylsulfone, which is a mono-rearranged product in which only one side of 4'-diallyloxydiphenylsulfone is rearranged, is determined by the weight of the raw material 4,4'-diallyloxydiphenylsulfone. 3,3′- which is a di-translocation product.
The reaction is terminated by suppressing the production of diallyl-4,4'-dihydroxydiphenylsulfone to 90% or less, and the resulting 3,3'-diallyl-4,4'-dihydroxydiphenylsulfone is the main component. The reaction product,
Recrystallization solvents include (A) at least one dichloroalkane solvent, (B) at least one aromatic solvent, and (C) alcohol-based or (and) glycol-based or (and) ether-based solvent. Recrystallization and purification using a solvent mixed with at least one of A method for producing '-diallyl-4,4'-dihydroxydiphenylsulfone.