JPS6056949A - Production of 4-substituted hydroxy-4'-hydroxydiphenyl sulfone - Google Patents
Production of 4-substituted hydroxy-4'-hydroxydiphenyl sulfoneInfo
- Publication number
- JPS6056949A JPS6056949A JP16413183A JP16413183A JPS6056949A JP S6056949 A JPS6056949 A JP S6056949A JP 16413183 A JP16413183 A JP 16413183A JP 16413183 A JP16413183 A JP 16413183A JP S6056949 A JPS6056949 A JP S6056949A
- Authority
- JP
- Japan
- Prior art keywords
- unreacted
- substituted hydroxy
- compound
- sulfone
- raw material
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は式
（式中Ｒはアルキル基、シクロアルキル基またはベン七
ン環に置換基を有してもよいベンジル基を表わす）で表
わされる４−ｆｆＬ換ヒドロキシ−４′−ヒドロキシジ
フェニルスルホンを純度よく且つ工業的に容易に製造す
る方法に関するものであって、 ４．４’−ジヒドロキ
シジフェニルスルホンをアルキル化、シクロアルキル化
またはベンジル化（そのベンジル基はベンセンｍｒｔｃ
ｒｉｔ換基な有してもよい）して４−置換ヒドロキシ−
４−ヒドロキシジフェニルスルホンを製造するに際し、
反応生成物である４−置換ヒドロキシ−４−ヒドロキシ
ジフェニルスルホンならひにそれと共存している未反応
の４，４′−ジヒドロキシジフェニルスルホンの水非混
和性有機溶媒溶液を炭酸水素塩水溶液と振盪して４，４
′−ジヒドロキシジフェニルスルホンを水層中に移行さ
せて除去する工程を含むことを特徴とする４−置換ヒド
ロキシ−４′−ヒドロキシジフェニルスルホンの製造方
法である。Detailed Description of the Invention The present invention provides 4-ffL-substituted hydroxy- This relates to a method for easily producing 4'-hydroxydiphenylsulfone with high purity on an industrial scale, the method comprising alkylating, cycloalkylating or benzylating 4'-dihydroxydiphenylsulfone (the benzyl group is benzene mrtc).
4-substituted hydroxy-
When producing 4-hydroxydiphenylsulfone,
If the reaction product is 4-substituted hydroxy-4-hydroxydiphenyl sulfone, a solution of unreacted 4,4'-dihydroxydiphenyl sulfone coexisting therein in a water-immiscible organic solvent is shaken with an aqueous bicarbonate solution. Te4,4
This is a method for producing 4-substituted hydroxy-4'-hydroxydiphenylsulfone, which comprises a step of transferring '-dihydroxydiphenylsulfone into an aqueous layer and removing it.
４−置換ヒドロキシ−４′−ヒドロキシジフェニルスル
ホンは感熱記録紙において顕色剤として使用される物質
である。それ自体は無色または淡色の電子供与発色性染
料をこの化合物と混合して紙面に塗布し、この紙面に熱
を加えればその加熱箇所が発色するのである。4-Substituted hydroxy-4'-hydroxydiphenyl sulfone is a substance used as a color developer in thermal recording paper. An electron-donating color-forming dye, which itself is colorless or light-colored, is mixed with this compound and applied to the paper surface, and when heat is applied to the paper surface, the heated areas become colored.
式（Ｉ＞においてＲがメチル基またはエチル基である物
質は特開昭５７−２１０８８６号公報に、Ｒがｎ−ブチ
ル基である物質は特開昭５８−２０４９６号公報に、ま
たＲがＣ４〜１２の直鎖アルキル基またはベンジル基（
置換基を有するもの゛もある）である物質は特開昭５８
−８２７Ｂ８号公報に記載されており、後２者の公開特
許公報にはそれらの物質の製造方法も記載されている。Substances in which R is a methyl group or ethyl group in formula (I>) are described in JP-A-57-210886, substances in which R is an n-butyl group are described in JP-A-58-20496, and R is a C4 ~12 linear alkyl groups or benzyl groups (
Substances that have substituents (some have substituents) are disclosed in Japanese Patent Application Laid-open No. 1983
-827B8, and methods for producing these substances are also described in the latter two published patent publications.
そしてそこに記載されている方法は４．４′−ジヒドロ
キシジフェニル（ヒスフェノール５）ＫＡ化アルキルま
たは塩化ベンジルを反応させ、中間処理ののち、粗生成
物をシリカゲルを用いたクロブトグラフィーによって精
製して４−置換ヒドロキシ−４′−ヒドロキシジフェニ
ルスルホンの純品ヲ得る方法である。The method described therein involves reacting 4,4'-dihydroxydiphenyl (hisphenol 5) with alkyl KA or benzyl chloride, and after an intermediate treatment, the crude product is purified by chromatography using silica gel. This is a method for obtaining pure 4-substituted hydroxy-4'-hydroxydiphenyl sulfone.
発明者等は工業的操業において大きな困難を伴うクロマ
トグラフィーを使用せずに４−置換ヒドロキシ−４′−
ヒドロキシジフェニルスルホンの高純度品を製造する方
法を探究する過程において、このクロマトグラフィーが
必要となる原因の物質が未反応の４，４′−ジヒドロキ
シジフェニルスルホンであることを見出した。この物質
はそれが４−置換ヒドロキシ−４′−ヒドロキシジフェ
ニルスルホン中に混在すると、その％がごくわずかであ
っても、その４− ｊｈ換ヒビトロキシ４′−ヒドロキ
シジフェニルスルホンを使用して製造した感熱記録紙の
地肌に汚れが生ずる。The inventors have discovered that 4-substituted hydroxy-4'-
In the process of searching for a method for producing a highly purified product of hydroxydiphenylsulfone, it was discovered that the substance that necessitates this chromatography is unreacted 4,4'-dihydroxydiphenylsulfone. When this substance is mixed in 4-substituted hydroxy-4'-hydroxydiphenyl sulfone, even if its percentage is very small, it will cause a heat Dirt appears on the background of the recording paper.
式（Ｉ）で表わされる４−置換ヒドロキシ−４−ヒドロ
キシジフェニルスルホンは４，４′−ビスヒドロキシジ
フェニルスルホンに常法に従ってそれとほぼ等モルのハ
ロゲン化アルキル、六ロゲン化シクロアルキル、ベンゼ
ン環に置換基を有してもよいハロゲン化ベンジルあるい
はジアルキル硫酸などの反応試薬を反応させることによ
って生成するが、この際４，４′−ジ匝換ヒドロキシジ
フエニルスルホンの副生を抑えるために。4-Substituted hydroxy-4-hydroxydiphenylsulfone represented by formula (I) is obtained by substituting 4,4'-bishydroxydiphenylsulfone with approximately equimolar alkyl halide, cycloalkyl hexahalide, or benzene ring according to a conventional method. It is produced by reacting a reaction reagent such as benzyl halide or dialkyl sulfate which may have a group, but in this case, the by-product of 4,4'-di-converted hydroxydiphenyl sulfone is suppressed.
それらの反応試薬を著しく大量使用したＩシ、あるいは
反・応条件を強めることは避けなければならないので、
原料である４、４′−ジヒドロキシジフェニルスルホン
の一部が未反応のまま反応系中にとどまることは不可避
である。そしてこの物質は種々の有機温媒に対する溶解
度が目的物の４−置換ヒドロキシ−４′−ヒドロキシジ
フェニルスルホンと大差がないので、再結晶によってこ
の目的物を完全に精製することは困難であり、クロマト
グラフィーによって精製せざるを得なかった。It is necessary to avoid using extremely large amounts of these reaction reagents or intensifying the reaction conditions.
It is inevitable that a part of the raw material 4,4'-dihydroxydiphenylsulfone remains unreacted in the reaction system. Since the solubility of this substance in various organic thermal media is not much different from that of the target substance, 4-substituted hydroxy-4'-hydroxydiphenylsulfone, it is difficult to completely purify this target substance by recrystallization, and chromatography is difficult. I had no choice but to purify it by photography.
発明者尋は４，４′−ジヒドロキシジフェニルスルホン
が４−ｆ１ｍヒドロキシ−４１−ヒドロキシジフェニル
スルホンにくらべて炭酸水素月の水浴液に対してはるか
に大きな浴）γ（＋１．を、１］することを見出して′
４−発明を完成したものである。すなわち４−置換ヒド
ロキシ−４７−ヒ゛ドロキシジフエニルスルホ／と４．
４’−’、；ヒドロキシシフエールスルホ／との両者を
溶解している水非混和性；ｌｆ機＃媒の溶液を炭敵水パ
塩の水γ６液と振盪ずれは前者は水層中にほとんど移行
しないのに対゛して後者は極めてよく移行するのであり
、この方法によって両者を極めて容易に分１１Ｆするこ
とかできる。The inventor Hiromu discovered that 4,4'-dihydroxydiphenylsulfone has a much larger effect on hydrogen carbonate (+1., 1) compared to 4-f1m hydroxy-41-hydroxydiphenylsulfone. Find out'
4-Complete the invention. That is, 4-substituted hydroxy-47-hydroxydiphenyl sulfo/ and 4.
4'-'; Water immiscible in which both hydroxyl and sulfo/ are dissolved; Shake the solution of the lf solvent with the water γ6 solution of carbon and water salt, and the former will be in the aqueous layer. While the latter hardly migrates, the latter migrates extremely well, and by this method both can be separated extremely easily.
水非混和性４１機溶媒としては例えばクロロホルム、四
塩化炭素、ジクロロエタン、パークレン、トリクレン、
クロロセン、メチルイソブチルケトン、ジブチルケトン
、ジエチルエーテル。Examples of water-immiscible solvents include chloroform, carbon tetrachloride, dichloroethane, perchlorene, trichlene,
Chlorocene, methyl isobutyl ketone, dibutyl ketone, diethyl ether.
シフチルエーテル、ベンゼン、トルエン、キシレン、モ
クロロベンゼン、０−ジクロロベンゼンなどを挙げるこ
とができ、炭酸水素塩水溶液としては例えば炭酸水素ナ
トリウム、炭酸水素カリウム、炭酸水素アンモニウム、
炭酸水素カルシウムなどの水溶液をあげることができる
。Examples of aqueous hydrogen carbonate solutions include cyphthyl ether, benzene, toluene, xylene, mochlorobenzene, and 0-dichlorobenzene. Examples of aqueous hydrogen carbonate solutions include sodium hydrogen carbonate, potassium hydrogen carbonate, ammonium hydrogen carbonate,
Examples include aqueous solutions such as calcium bicarbonate.
４．４’−’）ヒドロキシジフェニルスルホンと上記の
各種反応試薬との反応は水あるいはアルコール類、アセ
トン、ジメチルホルムアミド、ジメチルスルホン、アセ
トニトリルなどの有機溶媒中で脱酸剤の存在下で行われ
、あるいは４，４′−ジヒドロキシジフェニルスルホン
の水酸基ｉ個をアルカリ土類金属塩にしておいてから口
れらの溶媒中で行われる。従って本発明の方法を行うに
は、これらの溶媒中で反応を行ったのち溶媒を除去し、
残りを水非混和性有機ｒ８ｔ＃、に溶融し、この溶液を
炭酸水素塩水溶液と振盪して４．４’−ジヒドロキシジ
フェニルスルホンを有機溶媒層から完全に除いたのち有
機溶媒を蒸留によって除いて４−Ｄｔ置換ヒドロキシ４
′−ヒト゛ロキシジフェニルスルホンを回収し、必費に
応じてそれをさらＫ例えば再結晶によってｔ＃製し′Ｃ
その純品を得る。この工程中において例えば４４機溶媒
溶液の水洗、゛あるいは不必要な析出物の１去などの操
作を適宜実施することによつ°〔作業を容易にすること
ができる。4.4'-') The reaction between hydroxydiphenyl sulfone and the various reaction reagents mentioned above is carried out in the presence of a deoxidizing agent in an organic solvent such as water or alcohols, acetone, dimethylformamide, dimethylsulfone, acetonitrile, etc. Alternatively, i hydroxyl groups of 4,4'-dihydroxydiphenylsulfone are converted into alkaline earth metal salts and then the reaction is carried out in a suitable solvent. Therefore, in order to carry out the method of the present invention, the reaction is carried out in these solvents, the solvent is removed, and
The remainder was dissolved in water-immiscible organic r8t#, and this solution was shaken with an aqueous bicarbonate solution to completely remove 4,4'-dihydroxydiphenylsulfone from the organic solvent layer, and then the organic solvent was removed by distillation. 4-Dt substituted hydroxy 4
'-Hydrooxydiphenyl sulfone is recovered and, if necessary, further processed to produce T#, for example by recrystallization.
Get that pure product. During this step, the operation can be made easier by appropriately carrying out operations such as washing the solvent solution with water, or removing unnecessary precipitates.
反応に際して少数の４，４′−ジ政換ヒドロキシジフェ
ニルスルホンが副生ずることもあるか、この物質は有機
溶媒によく溶Ｗ（、Ｌ且つアルカリ水溶液にはほとんど
溶解しないので、この性質を利用して容易に除去するこ
とができる。A small amount of 4,4'-diformed hydroxydiphenyl sulfone may be produced as a by-product during the reaction, or this substance is well soluble in organic solvents and hardly soluble in alkaline aqueous solutions, so this property can be used to can be easily removed.
本発明の方法によって製造した４−置換ヒドロキシ−４
′−ヒドロキシジフェニルスルホ／の融点を第１表に示
す。これらの化合物の多・く・のものは参考例に準じて
感熱記録紙の顕色剤として使用することができる。4-substituted hydroxy-4 produced by the method of the present invention
The melting points of '-hydroxydiphenylsulfo/ are shown in Table 1. Many of these compounds can be used as color developers for thermosensitive recording paper according to the reference examples.
ｖ、１ 表
ｃ２Ｈ５−１５９，４〜１６１．５
ｒニーＣ５１→、−１５２５〜１５３．９１ｇｏ−Ｃ７
Ｈ７−１２９，０〜１３０．０ｎ−０４Ｈｐ−１１８，
０〜１１９．［ｌ１ｓｏ−Ｃ４Ｈｐ−９４，０〜９６．
２ｔｅｒ ｔ−Ｃ４Ｂ５＋−９８−６〜１００．４１５
ｅＣ−Ｃ４）１ｐ−油状
Ω−ＣｓＨ１７−６１
ｎ”’０１２Ｈ２５−油 状
（ＪＣ）（２−１６７，２〜１６９．０σ １２Ｚ４〜
１２９６
実施例 １
４，４′−ジヒドロキシジフェニルスルホン３０．０ノ
、インプロヒルブロマイド１８．４Ｍおよび炭酸カリウ
ム２２．２ｆをジメチルホルムアミド２００−中に加え
、１００〜１２０℃の温度で４時間指１゛１゜した。v, 1 Table c2H5-159,4-161.5 r knee C51→, -1525-153.91go-C7
H7-129, 0-130.0n-04Hp-118,
0-119. [l1so-C4Hp-94,0-96.
2ter t-C4B5+-98-6~100.415
eC-C4) 1p-oil Ω-CsH17-61 n”'012H25-oil (JC) (2-167, 2~169.0σ 12Z4~
1296 Example 1 30.0 g of 4,4'-dihydroxydiphenyl sulfone, 18.4 M of inprohylbromide and 22.2 f of potassium carbonate were added to 200 g of dimethylformamide and incubated at a temperature of 100-120° C. for 4 hours. It was 1°.
ジメチルホルムアミドを減圧下に留去し、ＩＢ、光物に
クロロホルム２００ａ＋４！と水２０１Ｊ−を加えて溶
解し、さらに少量の硫酸を加えて水層のｐＨを５．０と
して分液した。Dimethylformamide was distilled off under reduced pressure, and chloroform 200a+4 was added to the IB light source. and 201 J of water were added to dissolve the mixture, and a small amount of sulfuric acid was further added to adjust the pH of the aqueous layer to 5.0, and the layers were separated.
クロロホルム層に炭酸水素ナトリウムの１０チ水溶液２
００−を加えて振盪分液することを２回５つだ後のクロ
ロボルム層中には薄Ｊ脅クロマトグラフィーによって４
，４′−ジヒドロキシジフェニルスルホンの存在は認め
られなかった。このクロロホルム層を１００ｍの水で洗
滌したのち、クロロホルムを留去し、残留物をトルエン
で再結晶して４−イソプロポキシ−４′−ヒト゛ロキシ
ジフェニルスルホン２２．１を融点１２９０〜１６ａＯ
℃の微細な白色結晶として得た。Add 10% aqueous solution of sodium hydrogen carbonate to the chloroform layer.
After adding 00- and shaking and separating twice, the chloroborum layer was analyzed by thin J chromatography.
, 4'-dihydroxydiphenyl sulfone was not observed. After washing this chloroform layer with 100 m of water, the chloroform was distilled off and the residue was recrystallized with toluene to obtain 4-isopropoxy-4'-hydroxydiphenyl sulfone 22.1 with a melting point of 1290 to 16 aO.
Obtained as fine white crystals at ℃.
この４−インプロポキシ−４′−ヒドロキシジフェニル
スルホンを用いて製造した感熱記録紙は地肌が非常に白
く、その他の性能もすぐれていた（参考′ｖｉｎ参照）
。Thermal recording paper manufactured using this 4-impropoxy-4'-hydroxydiphenylsulfone had a very white background and had excellent other properties (see 'vin').
.
実施例 ２
４．４’−ジヒドロキシジフェニルスルホン１２５１を
ジメチルホルムアミド５００−に溶解し、さらに炭酸カ
リウム８２．Ｅｌおよびｎ−ブチルブロマイド１１０．
４Ｆを加え、１００〜１１０℃の温度で４時間攪拌を続
けたのちジメチルホルムアミドを留去した。Example 2 4. 4'-dihydroxydiphenylsulfone 1251 was dissolved in dimethylformamide 500, and potassium carbonate 82. El and n-butyl bromide 110.
After adding 4F and continuing stirring at a temperature of 100 to 110°C for 4 hours, dimethylformamide was distilled off.
残留物にクロロボルム７００ｆｎｌＶおよび水７００ｄ
を加えて沼解し、硫酸を加え”Ｃｐｋｌを約５として分
液した。クロロホルム層を炭阪水素ナトリウムの１０％
水溶液７００ｎｄで２回むＣ浄して未反応の４，４′−
ジヒドロキシジフェニルスルポンを除き、温湯５００−
で２回洗浄したのちクロロホルムを留去し、トルエンで
再結晶を行って４−ｎ−ブトキシ−４′−ヒドロキシジ
フエニルスルホン７２゜１ｆを融点１．１ ＆’Ｄ 〜
１１１９．０ ℃ノ白色結晶トシテ得た。The residue contains 700 fnlV of chloroborum and 700 d of water.
The chloroform layer was diluted with sulfuric acid and the Cpkl was set to about 5.The chloroform layer was diluted with 10%
Unreacted 4,4'-
Excluding dihydroxydiphenyl sulpon, warm water 500-
After washing twice with
White crystals were obtained at 1119.0°C.
この結晶を参考例に準じてｈ色剤として使用して製造し
た感熱記録紙は地肌に汚れを生じなかった。The thermosensitive recording paper produced using this crystal as an h coloring agent according to the reference example did not cause stains on the background.
なお上記の炭酸水素ナトリウム水浴液による洗浄液から
は４，４′−ジヒドロキシジフェニルスルホンが回収さ
れた。Note that 4,4'-dihydroxydiphenyl sulfone was recovered from the washing solution using the sodium bicarbonate water bath solution.
参考例
実施例１で製造した４−インプロポキシ−４１−ヒドロ
キシジフェニルスルホン１０．４Ｍ、ポリビニルアルコ
ール（株式会社クラレ、［クシレ−１０５Ｊ）の１５％
水溶液４１．５ ｒ 、無機：ｌＡオニ＋ ＜ Ｚンゲ
ルハルト社、「ＵＷ−９ＤＪ） ８．Ｏｆおよび純水４
０．０２をガラスピース（径１〜１，５叫）１５０ｒと
共に２５０ｆｎｌのポリエチレン瓶に入れ、密栓して）
ｋｄＤｅｖｉ１社製ペイントコンディショナーに装着し
、６３０回／分の振動数で８時ｆｌｄ＋振盪したのち、
カラスヒースを除去して粒度２〜６μの４−インプロポ
キシ−４′−ヒドロキシジフェニルスルホンの水性懸濁
液を得た（Ａ液）。Reference Example 10.4M of 4-inpropoxy-41-hydroxydiphenylsulfone produced in Example 1, 15% of polyvinyl alcohol (Kuraray Co., Ltd., [Kushire-105J)]
Aqueous solution 41.5 r, inorganic: 1A Oni+ <Z-Ngelhardt, "UW-9DJ" 8. Of and pure water 4
0.02 into a 250fnl polyethylene bottle with a glass piece (diameter 1 to 1.5 mm) of 150r, and seal it tightly.)
After attaching it to the kdDevi1 paint conditioner and shaking at 8:00 fld+ at a frequency of 630 times/min,
The glass heath was removed to obtain an aqueous suspension of 4-impropoxy-4'-hydroxydiphenylsulfone having a particle size of 2 to 6 microns (Liquid A).
他方３−Ｎ−メチルシクロヘキシルアミノ−６−メチル
−７−フェニルアミノフルオランＺＯり、ポリビニルア
ルコール（前記と同じ）ノ１５係水溶液４１．５ｔ、無
機填料（前記と同じ）１１．５２および純水４０．Ｏｆ
をガラスピーズ１５０ｔと共に２５０−のポリエチレン
瓶に入れ、密栓してペイントコンデイショーナーで６６
０回／分の振動数で５時間振盪したのち、カラスビーズ
を除去してフルオラン化合物の水性懸濁液（粒度２〜３
μ）を得た（Ｂ液）。On the other hand, 3-N-methylcyclohexylamino-6-methyl-7-phenylaminofluorane ZO, 41.5 tons of a 15% aqueous solution of polyvinyl alcohol (same as above), 11.52 tons of inorganic filler (same as above), and pure water. 40. Of
Put it in a 250mm polyethylene bottle with 150t of glass peas, seal it tightly, and add 66mm of paint conditioner.
After shaking for 5 hours at a frequency of 0 times/min, the glass beads were removed and an aqueous suspension of the fluoran compound (particle size 2-3
μ) was obtained (liquid B).
さらにポリビニルアルコール
の１５チ水？ｆ＝ＢＩ＆：４１．５Ｆ，無（伐項料（前
記に同じ）１８５２および純水４０．Ｏｆをガシスヒー
ズ１５０２と共に２５０＋＋＋７！ポリエチレン類に入
れ、上ｂＩシと同様に処理して無機填料の水性懸濁液を
得た（Ｃ徹）。Furthermore, 15% water of polyvinyl alcohol? f = BI &: 41.5F, no (logging fee (same as above) 1852 and pure water 40.Of are put in 250+++7! polyethylene with Gasis Heat 1502 and treated in the same manner as above bI to obtain an aqueous suspension of inorganic filler. A cloudy solution was obtained (Toru C).
Ａ液１ｏｙそしてＢ液およびＣ散の各５ｖを・混合し，
２０分間攪拌して塗布紙を製造した。Mix 1 oy of liquid A and 5 v each of liquid B and powder C,
A coated paper was prepared by stirring for 20 minutes.
この塗布叡火日色原紙にワイへ′ーロッド隘１２を用い
て塗布し６０℃の温風で２分間乾燥して感熱記録紙を製
造した。この感熱記録紙は地肌が非常に白かった。The coating was coated on the coated yellow base paper using a wire rod (12) and dried for 2 minutes with warm air at 60°C to produce heat-sensitive recording paper. This thermal recording paper had a very white background.
特許出願人 新日曹化工株式会社Patent applicant: Shin Nisso Kako Co., Ltd.
Claims (1)
化、シクロアルキル化またはベンジル化（そのベンジル
基はベン七ン環に置換基をイＪしてもよい）して式 （式中Ｒはアルキル基、シクロアルキル基またはベン七
ン環に置換基を有してもよいベンジル基を表わす）で表
わされる４−置換ヒドロキシ−４′−ヒドロキシジフエ
ニルスルホンを製造スるに際し、反応生成物である４−
置換ヒドロキシ−４′−ヒドロキシジフェニルスルホン
ならびにそれと共存している未反応の４，４′−ジヒド
ロキシジフェニルスルホンの水非混和性有機溶媒溶液を
炭酸水素塩水溶液と振盪して４，４′−ジヒドロキシジ
フェニルスルホンを水層中に移行させて除去する工程を
含むことを特徴とする、４−置換ヒドロキシ−４′−ヒ
ドロキシジフェニルスルホンの製造方法。[Scope of Claims] 4.4'-Dihydroxydiphenylsulfone is alkylated, cycloalkylated or benzylated (the benzyl group may have a substituent on the benzyl ring) to form the formula (in the formula R represents an alkyl group, a cycloalkyl group, or a benzyl group which may have a substituent on the ben7 ring). 4- which is a thing
A water-immiscible organic solvent solution of substituted hydroxy-4'-hydroxydiphenylsulfone and unreacted 4,4'-dihydroxydiphenylsulfone coexisting therewith is shaken with an aqueous bicarbonate solution to produce 4,4'-dihydroxydiphenyl. A method for producing 4-substituted hydroxy-4'-hydroxydiphenyl sulfone, which comprises a step of transferring sulfone into an aqueous layer and removing it.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16413183A JPS6056949A (en) | 1983-09-08 | 1983-09-08 | Production of 4-substituted hydroxy-4'-hydroxydiphenyl sulfone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16413183A JPS6056949A (en) | 1983-09-08 | 1983-09-08 | Production of 4-substituted hydroxy-4'-hydroxydiphenyl sulfone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6056949A true JPS6056949A (en) | 1985-04-02 |
| JPH0377187B2 JPH0377187B2 (en) | 1991-12-09 |
Family
ID=15787333
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16413183A Granted JPS6056949A (en) | 1983-09-08 | 1983-09-08 | Production of 4-substituted hydroxy-4'-hydroxydiphenyl sulfone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6056949A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63251685A (en) * | 1987-04-07 | 1988-10-19 | 東海カ−ボン株式会社 | Hybrid frp tubular body |
| US5284978A (en) * | 1990-01-29 | 1994-02-08 | Yoshitomi Pharmaceutical Industries, Ltd. | Method for producing diphenyl sulfone compounds |
| EP0997315A1 (en) * | 1998-10-29 | 2000-05-03 | Nicca Chemical Co., Ltd. | Polycyclic phenol compounds and heat-sensitive recording materials employing them |
| WO2000056705A1 (en) * | 1999-03-23 | 2000-09-28 | Nippon Soda Co., Ltd. | Industrial process for the production of diphenyl sulfone compounds |
| WO2002057221A1 (en) * | 2001-01-22 | 2002-07-25 | Nippon Soda Co.,Ltd. | Process for producing diphenyl sulfone compound |
| WO2003029202A1 (en) * | 2001-09-28 | 2003-04-10 | Konishi Chemical Ind. Co., Ltd. | 4-isopropoxy-4’-hydroxydiphenyl sulfone for developers, process for its production and thermal recording material |
| US6762200B2 (en) | 2000-03-28 | 2004-07-13 | Nippon Soda Co. Ltd. | Oxa(thia)zolidine derivative and anti-inflammatory drug |
| KR100529158B1 (en) * | 2002-11-14 | 2005-11-17 | 주식회사 코오롱 | Process for producing 4-isopropoxy-4'-hydroxydiphenyl sulfone |
| CN1318399C (en) * | 2001-01-22 | 2007-05-30 | 日本曹达株式会社<Del/> | Processes for the preparation of diphenylsulfone compounds |
| US7241924B2 (en) | 1999-03-23 | 2007-07-10 | Nippon Soda Co., Ltd. | Industrial process for the production of diphenyl sulfone compounds |
| JP2008133193A (en) * | 2006-11-27 | 2008-06-12 | Nicca Chemical Co Ltd | Method for producing alkyloxyhydroxydiphenyl sulfone |
-
1983
- 1983-09-08 JP JP16413183A patent/JPS6056949A/en active Granted
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63251685A (en) * | 1987-04-07 | 1988-10-19 | 東海カ−ボン株式会社 | Hybrid frp tubular body |
| US5284978A (en) * | 1990-01-29 | 1994-02-08 | Yoshitomi Pharmaceutical Industries, Ltd. | Method for producing diphenyl sulfone compounds |
| EP0997315A1 (en) * | 1998-10-29 | 2000-05-03 | Nicca Chemical Co., Ltd. | Polycyclic phenol compounds and heat-sensitive recording materials employing them |
| WO2000056705A1 (en) * | 1999-03-23 | 2000-09-28 | Nippon Soda Co., Ltd. | Industrial process for the production of diphenyl sulfone compounds |
| EP1860099A2 (en) | 1999-03-23 | 2007-11-28 | Nippon Soda Co., Ltd. | Industrial process for the production of diphenyl sulfone compounds |
| US7241924B2 (en) | 1999-03-23 | 2007-07-10 | Nippon Soda Co., Ltd. | Industrial process for the production of diphenyl sulfone compounds |
| US6762200B2 (en) | 2000-03-28 | 2004-07-13 | Nippon Soda Co. Ltd. | Oxa(thia)zolidine derivative and anti-inflammatory drug |
| CN1318399C (en) * | 2001-01-22 | 2007-05-30 | 日本曹达株式会社<Del/> | Processes for the preparation of diphenylsulfone compounds |
| WO2002057221A1 (en) * | 2001-01-22 | 2002-07-25 | Nippon Soda Co.,Ltd. | Process for producing diphenyl sulfone compound |
| KR100821548B1 (en) * | 2001-01-22 | 2008-04-14 | 닛뽕소다 가부시키가이샤 | Process for producing diphenyl sulfone compound |
| CN100383117C (en) * | 2001-01-22 | 2008-04-23 | 日本曹达株式会社 | Processes for the preparation of diphenylsulfone compounds |
| EP1930318A2 (en) | 2001-01-22 | 2008-06-11 | Nippon Soda Co., Ltd. | Process for producing diphenyl sulfone compound |
| US7619120B2 (en) | 2001-01-22 | 2009-11-17 | Nippon Soda Co., Ltd. | Processes for the preparation of diphenylsulfone compounds |
| WO2003029202A1 (en) * | 2001-09-28 | 2003-04-10 | Konishi Chemical Ind. Co., Ltd. | 4-isopropoxy-4’-hydroxydiphenyl sulfone for developers, process for its production and thermal recording material |
| KR100529158B1 (en) * | 2002-11-14 | 2005-11-17 | 주식회사 코오롱 | Process for producing 4-isopropoxy-4'-hydroxydiphenyl sulfone |
| JP2008133193A (en) * | 2006-11-27 | 2008-06-12 | Nicca Chemical Co Ltd | Method for producing alkyloxyhydroxydiphenyl sulfone |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0377187B2 (en) | 1991-12-09 |
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