JPS58203946A - Preparation of 3,3'-dinitro-4,4'-dichlorobenzophenone and 3,3'-dinitro-4,4'-dichlorodiphenyl sulfone - Google Patents
Preparation of 3,3'-dinitro-4,4'-dichlorobenzophenone and 3,3'-dinitro-4,4'-dichlorodiphenyl sulfoneInfo
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- JPS58203946A JPS58203946A JP8489082A JP8489082A JPS58203946A JP S58203946 A JPS58203946 A JP S58203946A JP 8489082 A JP8489082 A JP 8489082A JP 8489082 A JP8489082 A JP 8489082A JP S58203946 A JPS58203946 A JP S58203946A
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- dichlorobenzophenone
- dinitro
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Abstract
Description
【発明の詳細な説明】
本発明は、３，３′−ジニトロ−４，４′−ジクロロベ
ンゾフェノンおヨヒ６．３′−ジニトロ−４，４’ −
ジクロロジフェニルスルホンの製造方法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention provides 3,3'-dinitro-4,4'-dichlorobenzophenone and 6,3'-dinitro-4,4'-
The present invention relates to a method for producing dichlorodiphenyl sulfone.
さらに計しくは、４，４′−ジクロロベンゾフェノンｉ
タハ４．４’−ジクロロジフェニルスルホ族ハロゲン
炭化水素溶剤中ニトロ化することを特徴とする３，３′
−ジニトロ−４．４′−ジクロロベンゾフェノンまたは
３．３′−ジニトロ−４．４′−ジクロロジフェニルス
ルホンの製造方法に関するものである。More specifically, 4,4'-dichlorobenzophenone i
Taha 4.4'-3,3' characterized by nitration in a 4'-dichlorodiphenylsulfo group halogen hydrocarbon solvent
-Dinitro-4,4'-dichlorobenzophenone or 3,3'-dinitro-4,4'-dichlorodiphenylsulfone.
３、３’−ジニトロ−４． ４’ − シクロロベンゾ
フエノンオヨヒ３．３’−ジニトロ−４，４′−ジクロ
ロジフェニルスルホンは磯医薬または耐熱性樹脂原料な
どの中間体として有用な物質である。3,3'-dinitro-4. 4'-Cyclobenzophenone 3,3'-dinitro-4,4'-dichlorodiphenyl sulfone is a substance useful as an intermediate for pharmaceuticals or raw materials for heat-resistant resins.
従来、これらの化合物は４．４′−ジクロロベンゾフェ
ノンまたは４．４′−ジクロロジフェニルスルホンのニ
トロ化により製造されることは公知である。It is conventionally known that these compounds can be prepared by nitration of 4,4'-dichlorobenzophenone or 4,4'-dichlorodiphenylsulfone.
例えば、ろ、３′−ジニトロ−４．４′−ジクロロベン
ゾフェノンの場合， ４１４’−ジクロロベンゾフェ
ノン 。For example, in the case of 3'-dinitro-4,4'-dichlorobenzophenone, 414'-dichlorobenzophenone.
を硝酸または硝酸ナトリウムと硫酸でニトロ化する方法
（ ｇ．Ｒ， ＫａｆａＵｙらＪ， ０４ｍ． Ｏム−
σｆ ＵＳＳＲ１５、９８〜１００（１９７９））があ
る。一方、３．３’−ジニトロ−４，４′−ジクロロジ
フェニルスルホンの場合モ、４＋ ”−ジクロロジフェ
ニルスルホンニ対して過剰の混酸を用いてニトロ化する
方法（ ｆ３＜４４四，６４０（１９０７）、竹谷ら特
開昭５２−１４７４４号）がある。A method of nitrating with nitric acid or sodium nitrate and sulfuric acid (g.R, KafaUy et al. J, 04m. Om-
σf USSR 15, 98-100 (1979)). On the other hand, in the case of 3,3'-dinitro-4,4'-dichlorodiphenylsulfone, there is a method of nitration using an excess of mixed acid with respect to 4+''-dichlorodiphenylsulfone (f3<444,640 (1907)). , Taketani et al., JP-A-52-14744).
しかしながら、これらはいずれも混酸便用量が多く廃酸
の後処理が問題となる。また反応終了後、反応系から目
的物を取り出す際目的物が粒状になりやすく、原料およ
び酸が結晶内に取り込まれ、高純度品が得られ難く、さ
らに後処理も容易でない。また、混酸から直ちに析出し
た結晶をｆ過して目的物を得る方法は作業上に問題があ
り、工業的な製造法ではない。さらに、通常、ニトロ化
反応では多量の発熱を伴なうの゛で、原料を少量ずつ添
加するか、効率の良い冷却装置が必要となり、作業上ま
たは経済性の面で不利である。このようにこれらの方法
を工業的に実施することは種々の難点がある。However, in all of these methods, the amount of mixed acid feces is large, and post-treatment of the waste acid poses a problem. Further, when the target product is removed from the reaction system after the reaction is completed, the target product tends to become granular, and the raw materials and acid are incorporated into the crystals, making it difficult to obtain a highly pure product and furthermore, post-treatment is not easy. Furthermore, the method of obtaining the desired product by filtering the crystals immediately precipitated from the mixed acid has operational problems and is not an industrial production method. Furthermore, the nitration reaction usually involves a large amount of heat generation, so it is necessary to add the raw materials little by little or to use an efficient cooling device, which is disadvantageous in terms of operation and economy. As described above, there are various difficulties in implementing these methods industrially.
したがって、４．４’−ジクロロベンゾフェノンまたハ
４，４′−ジクロロジフェニルスルホンをニトロ化する
除、生成する発熱をｂ 鼻（、に開側１することおよび
混酸の使用量を出来るだけ低減させ、かつ反応の後処理
が容易であり、しかも、高収率で高純度の結晶性の３．
３′−ジニトロ−４，４′−ジクロロベンゾフェノン、
３．３’−ジニトロ−４，４’−ジクロロ要望されてい
る課題である。Therefore, when nitrating 4,4'-dichlorobenzophenone or 4,4'-dichlorodiphenylsulfone, the generated heat should be kept open and the amount of mixed acid used should be reduced as much as possible. 3. The post-treatment of the reaction is easy, and moreover, it has high yield and high purity crystallinity.
3'-dinitro-4,4'-dichlorobenzophenone,
3.3'-dinitro-4,4'-dichloro This is a desired problem.
本発明者らは、４．４’−ジクロロベンゾフェノンおよ
び４．４′−ジクロロジフェニルスルホンのニトロ化に
ついて鋭意検討した結果、脂肪族）・ロゲン化炭化水素
溶剤中でニトロ化を行なうと反応が円滑に進行し、高収
率、高純度で、しかも結晶性の３．３′−ジニトロ−４
，４′−ジクロロベンゾフェノ／および３．３′−ジニ
トロ−４，４′−ジクロロジフェニルスルホンが製造で
きることを見出し、本発明に到達した。As a result of intensive studies on the nitration of 4,4'-dichlorobenzophenone and 4,4'-dichlorodiphenylsulfone, the present inventors found that the reaction is smoother when the nitration is carried out in an aliphatic/logenated hydrocarbon solvent. The process proceeds to produce high yield, high purity, and crystalline 3,3'-dinitro-4.
, 4'-dichlorobenzopheno/ and 3,3'-dinitro-4,4'-dichlorodiphenyl sulfone, and have arrived at the present invention.
本発明の方法は、脂肪族ノ・ロゲン化炭化水素を４１、
とじて使用することによって、はじめて前記の目的が達
成される。すなわち、反応熱の制御が容易であり、混酸
の使用量が低減でき、かつ溶剤の回収も容易で、必要に
応じて丹使用も可能であｒ）、ｓ、ｓ’−ジニトロ−４
，４′−ジクロロベンゾフェノンおヨヒ３．５′−ジニ
トロ−４，４’−ジクロロジフェニルスルホンを高収率
、高純度で製造できる。The method of the present invention comprises converting an aliphatic non-logenated hydrocarbon into 41,
Only by using it together can the above-mentioned objective be achieved. That is, the reaction heat can be easily controlled, the amount of mixed acid used can be reduced, and the solvent can be easily recovered, and it is also possible to use red if necessary.
, 4'-dichlorobenzophenone and 3,5'-dinitro-4,4'-dichlorodiphenyl sulfone can be produced in high yield and with high purity.
本発明の方法で使用される浴剤は脂肪１＆ノ・ロゲン化
炭化水素溶剤である。The bath agent used in the process of the invention is a fatty and non-rogenated hydrocarbon solvent.
例えば、ジクロロメタン、クロロホルム、四基化炭素、
１．１−ジクロロエタン、１，２−ジクロロエタン、１
．１．１− ）ジクロロエタン、１．１．２− ）ジク
ロロエタン、 １．ｉ、１．２−ナト５クロロエタ７
．１、１．２．２−テトラクロロエタン、１．２−ジク
ロロエチレン、トリクロロエチレン、テトラクロロエチ
レンなどが挙げられる。For example, dichloromethane, chloroform, carbon tetracarbon,
1.1-dichloroethane, 1,2-dichloroethane, 1
．． 1.1-) dichloroethane, 1.1.2-) dichloroethane, 1. i, 1,2-nato5 chloroetha7
．． Examples include 1,1.2.2-tetrachloroethane, 1,2-dichloroethylene, trichlorethylene, and tetrachloroethylene.
溶剤の使用量は特に制限はないが、通常、原料の４．４
′−ジクロロベンゾフェノンまたは４，４′−ジクロロ
ジフェニルスルホンに対して０２〜２０重量倍量で使用
される。好ましくは１〜１０市被倍楡である。There is no particular limit to the amount of solvent used, but it is usually 4.4% of the raw material.
It is used in an amount of 02 to 20 times the weight of '-dichlorobenzophenone or 4,4'-dichlorodiphenylsulfone. Preferably 1 to 10 elms are covered.
本発明の方法において、ニトロ化剤としては混酸、また
は硝酸塩と硫酸が用いられる。In the method of the present invention, mixed acids or nitrates and sulfuric acid are used as the nitrating agent.
原料ノ４．４’−ジクロロベンゾフェノンまたは４．４
′−ジクロロジフェニルスルホンに対する硝唯の使用量
は２０〜５０倍モル、特に２．２〜３０倍モルが好まし
い。Raw material 4.4'-dichlorobenzophenone or 4.4
The amount of nitrate to be used is preferably 20 to 50 times, particularly 2.2 to 30 times, by mole relative to '-dichlorodiphenylsulfone.
硝ｔｌｌｔ諜度については特に制限はないが、通常、比
重１３０〜１．５２の硝酸を用いる。特に比重１．４２
〜１，５０の硝酸が好ましい。There are no particular restrictions on the nitric acid content, but nitric acid with a specific gravity of 130 to 1.52 is usually used. Especially specific gravity 1.42
~1,50 nitric acid is preferred.
硝酸塩の使用量は２〜３倍モル、特に２．１〜２５倍モ
ルが好ましい。硝酸塩としては通常硝酸す） ＩＪウム
、硝酸カリウムが用いられる。The amount of nitrate used is preferably 2 to 3 times the mole, particularly 2.1 to 25 times the mole. As nitrates, nitric acid, potassium nitrate, and potassium nitrate are usually used.
また、（＃酸のイφ用量は２〜８倍モル、特に４〜６倍
モルが好ましい。硫酸の濃度は７０％以上であればさし
つかえない。In addition, the amount of (# acid) is preferably 2 to 8 times the molar amount, particularly 4 to 6 times the molar amount.The concentration of sulfuric acid may be 70% or more.
本発明の方法の実癩に際しては、原料の４．４’−ジク
ロロベンゾフェノンまたは４．４′−ジクロロジフェニ
ルスルホンを有機溶剤に混合した後、混ばを滴下するか
、混酸に４．４′−ジクロロベンゾフェノンマタハ４．
４′−ジクロロジフェニルスルホンを加えた後有機溶剤
を加えるか、またあらかじめ有機溶剤に混酸を混合し、
４．４′−ジクロロベンゾフェノンマタはａ、ａ’−ジ
クロロジフェニルスルホンを加えてもよい。なお、硝酸
の替りに硝酸塩を使用した褐合、原料の４．４′−ジク
ロロベンゾフェノン４ ｔ、−ハ４．４− ジクロロジ
フェニルスルホンな有機溶剤に混合した後、硝酸塩を加
えて硫酸を個下する方法が多用される。反応温度は２０
〜１００’Ｃで、特に４０〜８０°Ｃが好ましい。反応
は、通常、２〜１０時間で進行する。When carrying out the method of the present invention, the raw material 4,4'-dichlorobenzophenone or 4,4'-dichlorodiphenylsulfone is mixed with an organic solvent, and then the mixture is added dropwise to the mixed acid. Dichlorobenzophenone Mataha 4.
After adding 4'-dichlorodiphenylsulfone, add the organic solvent, or mix the mixed acid with the organic solvent in advance,
4. A, a'-dichlorodiphenyl sulfone may be added to 4'-dichlorobenzophenone. In addition, for browning using nitrate instead of nitric acid, the raw material 4,4'-dichlorobenzophenone is mixed with an organic solvent such as 4,4'-dichlorodiphenylsulfone, and then nitrate is added and sulfuric acid is added. This method is often used. The reaction temperature is 20
˜100°C, particularly preferably 40-80°C. The reaction usually proceeds in 2 to 10 hours.
反応後有機層と混酸層を分離し、有機層について溶剤を
留去し一過、水洗、乾燥して６．５′−ジニトロ−４，
４’−ジクロロベンゾフェノンまたハ３．５’−シニト
ロー４，４′−ジクロロジフェニルスルホンの結晶を高
収率高純度で得ることが出来る。また混酸層からは、必
要に応じて混酸を回収し、これを次のニトロ化に利用す
ることも可能である。After the reaction, the organic layer and mixed acid layer were separated, and the solvent was distilled off from the organic layer, passed through, washed with water, and dried to obtain 6,5'-dinitro-4,
Crystals of 4'-dichlorobenzophenone or 3,5'-sinitro-4,4'-dichlorodiphenylsulfone can be obtained in high yield and purity. Further, it is also possible to recover the mixed acid from the mixed acid layer as needed and use it for the next nitration.
以上述べた方法は典型的な例であり、有機層と混。The method described above is a typical example and does not mix with the organic layer.
酸層を分離せず直ちに水で希釈し、そのまま溶剤を留去
し、目的物を得ることも可能である。It is also possible to directly dilute the acid layer with water without separating it, and then directly distill off the solvent to obtain the desired product.
以下、本発明の方法を実施例をあげてさらに成体的に祝
明する。Hereinafter, the method of the present invention will be explained in more detail with reference to Examples.
実施例１
４．４′−ジクロロベンゾフェノン５０．２＠（０，２
モル）を１２−ジクロルエタン１０．ｏｍｇに溶解させ
る。室温で硝酸（比重１．５０）２８．２．９を加えた
のち、３０〜４０’Ｏで９８％硫、酸１１７ｇを５０分
ｉ司で滴下する。さらに７０〜８０°Ｃで８時間かきま
ぜた後冷却し、有機層と混酸層を分液する。さらに水１
ｏｏｍｇを使用して洗浄、分液した溶液の溶剤を水蒸気
蒸留により留去して、結晶をＰ別、水洗、乾燥して３，
６′−ジニトロ−４，４′−ジクロロベンゾフェノンの
淡黄色プリズム状結晶を得た。Example 1 4.4'-dichlorobenzophenone 50.2@(0,2
10. mol) of 12-dichloroethane. Dissolve in omg. After adding 28.2.9 g of nitric acid (specific gravity 1.50) at room temperature, 117 g of 98% sulfuric acid was added dropwise over 50 minutes at 30-40'O. After further stirring at 70 to 80°C for 8 hours, the mixture is cooled and separated into an organic layer and a mixed acid layer. 1 more water
The solvent of the solution washed and separated using oomg was distilled off by steam distillation, and the crystals were separated from P, washed with water, and dried.
Pale yellow prismatic crystals of 6'-dinitro-4,4'-dichlorobenzophenone were obtained.
収ｉ６Ｂ、２ｇ（収率９９％）、高速液体クロマトグラ
フィーによる純度は９９．７係であった。融点１３１〜
１５２．５’Ｏ。The yield was 2 g (99% yield) of i6B, and the purity by high performance liquid chromatography was 99.7. Melting point 131~
152.5'O.
エタノールから再結晶して淡黄色プリズム状結晶の純品
を得た。融点１３２５°ｃ。Recrystallization from ethanol yielded pure pale yellow prismatic crystals. Melting point 1325°c.
元素分析 ＣＨＮ ＯＲ
計算イロ垂Ｌ（％） ４５，７６ １，
７６ ８．２１ ２０．８０測定値（＠
４５，８０ １．７８ ８．２５ ２０．８２
実施例２
４．４′−ジクロロベンゾフェノン５０．２ｐ（０，２
モル）を９８％硫騒１１７１に添加した後、１．１．１
一トリクロロエタンｉｏｏｍｇを加え、硝酸（比重１．
４２）５３．７ｐを滴下する。さらに７０〜８０８Ｃで
１０時間かきまぜたのち、冷却して有機層と（１１゜離
層を分液し、溶剤を水蒸気蒸留により留去して結晶を口
利、水洗、乾燥して、ロ、３′−ジニトロー４４′−ジ
クロロベンゾフェノンの淡黄色ブ１ノズム状結晶を得た
。収量６Ｂ、２ｇ（収率９９係）、四速液体クロマトグ
ラフィーによる純度１１９９５チであった。融点１５１
〜１３２５°Ｃ０
実施例３
４４′−ジクロロベンゾフェノン５０．２．９（０，２
モル）ヲ１，２−ジクロロエタン１０ ＣＪｍｌ＠％４
サセ、硝酸ナトリウム６７４ｇを加え゛たのち、３０〜
４Ｄ０Ｃにて９８φ硫酸１２０ｇを３０分間で滴下する
。Elemental analysis CHN OR Calculation Irotari L (%) 45,76 1,
76 8.21 20.80 Measured value (@
45,80 1.78 8.25 20.82
Example 2 4.4'-dichlorobenzophenone 50.2p (0,2
1.1.1 after adding mol) to 98% sulfur 1171
Add iomg of monotrichloroethane and add nitric acid (specific gravity 1.
42) Drop 53.7p. After further stirring at 70 to 808C for 10 hours, it was cooled and separated into an organic layer (11°), the solvent was distilled off by steam distillation, the crystals were washed with water, dried, and '-Dinitro-44'-dichlorobenzophenone was obtained as pale yellow, monochromatic crystals. Yield: 6B, 2 g (yield: 99), purity as determined by four-speed liquid chromatography: 11,995 cm. Melting point: 151
~1325°C0 Example 3 44'-dichlorobenzophenone 50.2.9 (0,2
mole) 1,2-dichloroethane 10 CJml@%4
After adding sasse and 674g of sodium nitrate, 30~
At 4D0C, 120g of 98φ sulfuric acid was added dropwise over 30 minutes.
さらに７０〜８０°Ｃで８時間かきまぜたのち、？６却
し水ＡＯａｌを加え生成した硫酸ナトリウムを溶解し有
機層と混酸層を分液する。さらに水１００ｍｅを使用し
て洗浄、分液した溶液の溶剤を水蒸気蒸留により留去し
て結晶を口利、水洗、乾燥し、６，６′−ジニトロ−４
，４′−ジクロロベンゾフェノンの淡黄色プリズム状の
結晶を得た。収量６６．８ｇ＜収率９８％）高速゛液体
クロマトグラフィーによる靜尼度は９９７Ｓであった。After stirring for another 8 hours at 70-80°C, ? 6. Add cooled water AOal to dissolve the produced sodium sulfate and separate the organic layer and mixed acid layer. Further, the solvent of the solution was washed with 100 m of water and separated by steam distillation, and the crystals were washed with water and dried.
, 4'-dichlorobenzophenone was obtained in the form of pale yellow prisms. Yield: 66.8 g <Yield: 98%) The purity determined by high performance liquid chromatography was 997S.
融点１３１〜１５２５°Ｃ０実画例４
４４′−ジクロロジフェニルスルホン５７．４ｇ（０２
モル）ヲ１．２−ジクロロエタン１７０ｍ１をカロえる
。室温で硝酸（比重１．５０）２８．２ｇをカロえたま
ぜた後冷却し有機層と混酸層を分液し、溶存１を水蒸気
蒸留に留去して結晶を口利、水洗、乾燥し３、３’ −
ジニトロ−４，４’−ジクロロジフェニルスルホンの針
状結晶を得た。収量７４６ｇ（収率９９％）尚速液体ク
ロマトグラフィーによる純度は９９６％であった。融点
２０１〜２０２°０゜エタノールから再結晶して針状結
晶の純品を得た。Melting point 131-1525°C0 Illustration example 4 44'-dichlorodiphenylsulfone 57.4g (02
mol) Add 170 ml of 2-dichloroethane. After stirring 28.2 g of nitric acid (specific gravity 1.50) at room temperature, the mixture was cooled, the organic layer and the mixed acid layer were separated, the dissolved 1 was distilled off by steam distillation, and the crystals were washed with water and dried. ,3'-
Needle-shaped crystals of dinitro-4,4'-dichlorodiphenylsulfone were obtained. Yield: 746 g (yield: 99%); purity as determined by instant liquid chromatography was 996%. It was recrystallized from ethanol with a melting point of 201-202°0 to obtain a pure product in the form of needle-like crystals.
一点２０１〜２０２ｕＣ０
元素分析 ＯＨＮ Ｓ Ｃ１計′卿１阻
（→ ３Ｂ、２１ １，５９ ７．４３ ８
．４９ １８．８１測定＋ｒＫ（＠３８，２６ １．
６０ ７．４１ ８．５２ １８．８２実施例５〜８
原料の４，４′−ジクロロベンゾフェノンまたＧま４．
４′−ジクロロジフェニルスルポンを使用して、溶剤の
種類と使用ｔ；“、硝酸、硫酸の使用量および反応温度
と反応時間を表−１のように変えたほがは実施例１と同
様な方法で目的物を得た。One point 201~202uC0 Elemental analysis OHN S C1 total 1 block (→ 3B, 21 1,59 7.43 8
．． 49 18.81 measurement + rK (@38,26 1.
60 7.41 8.52 18.82 Examples 5 to 8 Raw material 4,4'-dichlorobenzophenone or G4.
Using 4'-dichlorodiphenyl sulfone, the method was the same as in Example 1 except that the type and amount of solvent used, the amounts of nitric acid and sulfuric acid, and the reaction temperature and reaction time were changed as shown in Table 1. Obtained the object in a certain way.
結果を実施例１〜４とともに表−１に示した。The results are shown in Table 1 together with Examples 1 to 4.
／/
Claims (1)
−ジクロロジフェニルスルホ゛ン１＝ｔｔｊ［）１０ゲ
ン炭化水素溶剤中でニトロ化することを特徴とする３、
３’−ジニトロ−４，４′−ジ−クロロベンゾフェノン
またはろ、３′−ジニトロ−４，４′−ジクロロジフェ
ニルスルホンの’Ｍ 遣方法。1) 4.4'-dichlorobenzophenone or 4.4'
-dichlorodiphenylsulfone 1=ttj[)10, characterized in that it is nitrated in a hydrocarbon solvent,
Method for using 3'-dinitro-4,4'-di-chlorobenzophenone or 3'-dinitro-4,4'-dichlorodiphenyl sulfone.
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8489082A JPS58203946A (en) | 1982-05-21 | 1982-05-21 | Preparation of 3,3'-dinitro-4,4'-dichlorobenzophenone and 3,3'-dinitro-4,4'-dichlorodiphenyl sulfone |
| US06/454,973 US4556738A (en) | 1982-01-12 | 1983-01-03 | Process for preparation of 3,3'- or 3,4'-diamino benzophenone |
| NLAANVRAGE8300074,A NL189406C (en) | 1982-01-12 | 1983-01-11 | PROCESS FOR THE PREPARATION OF 3,3 'OR 3,4' DIAMINOBENZOPHENONE. |
| GB08300598A GB2116168B (en) | 1982-01-12 | 1983-01-11 | Process for preparing of 3,3'- or 3,4' -diamino benzophenone |
| FR8300403A FR2519631B1 (en) | 1982-01-12 | 1983-01-12 | PROCESS FOR THE PREPARATION OF 3,3'- OR 3,4'-DIAMINO BENZOPHENONE |
| CA000419346A CA1182129A (en) | 1982-01-12 | 1983-01-12 | Process for preparation of 3,3'-or 3,4'- diaminobenzophenones |
| CH137/83A CH655304A5 (en) | 1982-01-12 | 1983-01-12 | PROCESS FOR THE PREPARATION OF DIAMINO-3,3 'OR -3,4' BENZOPHENONE. |
| DE3300821A DE3300821C2 (en) | 1982-01-12 | 1983-01-12 | Process for the preparation of 3,3'- or 3,4'-diaminobenzophenone |
| IT8319267A IT1212692B (en) | 1982-04-13 | 1983-01-25 | Di:amino-benzophenone prodn. |
| GB08304332A GB2118542B (en) | 1982-02-18 | 1983-02-16 | Process for preparing of 3,3'-diamino diphenylsulfones |
| AU11452/83A AU553454B2 (en) | 1982-02-18 | 1983-02-16 | Preparation of 3,3:-diaminodiphenyl sulfones |
| CA000421816A CA1193283A (en) | 1982-02-18 | 1983-02-17 | Process for preparing 3,3'-diamino diphenysulfones diphenylsulfones |
| KR1019830000634A KR870001156B1 (en) | 1982-02-18 | 1983-02-17 | Process for preparing 3,3'-diamino diphenylsulfones |
| FR8302683A FR2521556B1 (en) | 1982-02-18 | 1983-02-18 | PROCESS FOR THE PREPARATION OF 3, 3'-DIAMINO-DIPHENYLSULFONES |
| IT19647/83A IT1193677B (en) | 1982-02-18 | 1983-02-18 | PROCESS TO PREPARE 3,3'-DIAMMINO-DIFENILSOLFONI |
| DE19833305654 DE3305654A1 (en) | 1982-02-18 | 1983-02-18 | METHOD FOR PRODUCING 3,3'-DIAMINODIPHENYL SULPHONES |
| US06/466,498 US4482742A (en) | 1982-02-18 | 1983-04-12 | Process for preparing of 3,3'-diamino diphenylsulfones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8489082A JPS58203946A (en) | 1982-05-21 | 1982-05-21 | Preparation of 3,3'-dinitro-4,4'-dichlorobenzophenone and 3,3'-dinitro-4,4'-dichlorodiphenyl sulfone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS58203946A true JPS58203946A (en) | 1983-11-28 |
Family
ID=13843344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8489082A Pending JPS58203946A (en) | 1982-01-12 | 1982-05-21 | Preparation of 3,3'-dinitro-4,4'-dichlorobenzophenone and 3,3'-dinitro-4,4'-dichlorodiphenyl sulfone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58203946A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01146878A (en) * | 1987-12-04 | 1989-06-08 | Mitsui Toatsu Chem Inc | Production of nitro-substituted tetraphenyl-thiophene-1,1-dioxides |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4844210A (en) * | 1971-10-06 | 1973-06-26 | ||
| JPS5148640A (en) * | 1974-10-15 | 1976-04-26 | Mitsui Toatsu Chemicals | 55 nitoro 144 nafutokinonno seizohoho |
-
1982
- 1982-05-21 JP JP8489082A patent/JPS58203946A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4844210A (en) * | 1971-10-06 | 1973-06-26 | ||
| JPS5148640A (en) * | 1974-10-15 | 1976-04-26 | Mitsui Toatsu Chemicals | 55 nitoro 144 nafutokinonno seizohoho |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01146878A (en) * | 1987-12-04 | 1989-06-08 | Mitsui Toatsu Chem Inc | Production of nitro-substituted tetraphenyl-thiophene-1,1-dioxides |
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