JPS6383078A - Production of benzofurazan-1-oxide - Google Patents
Production of benzofurazan-1-oxideInfo
- Publication number
- JPS6383078A JPS6383078A JP22488986A JP22488986A JPS6383078A JP S6383078 A JPS6383078 A JP S6383078A JP 22488986 A JP22488986 A JP 22488986A JP 22488986 A JP22488986 A JP 22488986A JP S6383078 A JPS6383078 A JP S6383078A
- Authority
- JP
- Japan
- Prior art keywords
- surfactant
- reaction
- nitroaniline
- benzofurazan
- oxide
- 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.)
- Pending
Links
- OKEAMBAZBICIFP-UHFFFAOYSA-N 3-oxido-2,1,3-benzoxadiazol-3-ium Chemical compound C1=CC=CC2=[N+]([O-])ON=C21 OKEAMBAZBICIFP-UHFFFAOYSA-N 0.000 title claims description 22
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000004094 surface-active agent Substances 0.000 claims abstract description 17
- -1 alkali metal hypochlorite Chemical class 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 12
- 239000007810 chemical reaction solvent Substances 0.000 claims abstract description 11
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Inorganic materials Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000003945 anionic surfactant Substances 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 4
- 239000005708 Sodium hypochlorite Substances 0.000 abstract description 3
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000975 dye Substances 0.000 abstract description 2
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 abstract description 2
- SATVIFGJTRRDQU-UHFFFAOYSA-N potassium hypochlorite Chemical compound [K+].Cl[O-] SATVIFGJTRRDQU-UHFFFAOYSA-N 0.000 abstract description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000003460 sulfonic acids Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003125 aqueous solvent Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000009775 high-speed stirring Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003444 phase transfer catalyst Substances 0.000 description 2
- QJGDGUBLGKFNDB-UHFFFAOYSA-N 1-azido-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1N=[N+]=[N-] QJGDGUBLGKFNDB-UHFFFAOYSA-N 0.000 description 1
- 108010088249 Monogen Proteins 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は染料などの中間体として有用なベンゾフラザン
−１−オキシドの製造方法に関するものであって、さら
に詳しくは下式（１）で示される２−ニトロアニリン又
はその誘導体を水溶媒中で、アルカリ金属次亜塩素酸塩
で酸化し、下式（ｎ）で示されるベンゾフラザン−１−
オキシド又はその誘導体を製造する方法の改良に係る。Detailed Description of the Invention [Industrial Application Field] The present invention relates to a method for producing benzofurazan-1-oxide, which is useful as an intermediate for dyes, etc., and more specifically, it is represented by the following formula (1). 2-Nitroaniline or a derivative thereof is oxidized with an alkali metal hypochlorite in an aqueous solvent to produce benzofurazan-1- represented by the following formula (n).
This invention relates to improvements in methods for producing oxides or derivatives thereof.
↑
（１） （ｎ）
但し、Ｒは水素、ハロゲン、０１〜Ｃ４のアルキル基又
は００〜Ｃ４のアルコキシ基を示す。↑ (1) (n) However, R represents hydrogen, halogen, an 01-C4 alkyl group, or a 00-C4 alkoxy group.
［従来の技術］
ベンゾフラザン−１−オキシドの製造方法に関しては、
幾つかの方法が公知である６例えば、２−ニトロアニリ
ンから２−二トロフェニルアジドを経由してベンゾフラ
ザン−１−オキシドを製造する方法〔バイルシュタイン
、？、Ｈ，６０１； Ｏｒｇ。[Prior Art] Regarding the manufacturing method of benzofurazan-1-oxide,
Several methods are known.6 For example, a method for producing benzofurazan-1-oxide from 2-nitroaniline via 2-nitrophenyl azide [Beilstein, et al. , H, 601; Org.
５ｙｎｔｈ、第３１巻１４頁以降（１９５１）： フラ
ンス特許第１，３９５，８８６号参照〕や、アルカリ金
属次亜塩素酸塩の水溶液を２−ニトロアニリンのアルカ
リ性アルコール溶液に混合してベンゾフラザン−１−オ
キシドを製造する方法〔バイルシュタイン、２７゜ＥＩ
、６２２： Ｏｒｇ、５ｙｎｔｈ、第３７巻１頁以降（
１９５Ｇ）参照〕がその例である。このうち、前者の方
法は反応工程が長い上に煩雑で、収率が低い難点が有り
。5ynth, Vol. 31, p. 14 et seq. (1951): French Patent No. 1,395,886], or by mixing an aqueous solution of an alkali metal hypochlorite with an alkaline alcoholic solution of 2-nitroaniline to prepare benzofurazan-1. - Method for producing oxide [Beilstein, 27゜EI
, 622: Org, 5ynth, Vol. 37, p. 1 et seq. (
195G)] is an example. Among these, the former method has the drawbacks of long and complicated reaction steps and low yield.
また後者の方法はベンゾフラザン−１−オキシドが高収
率で得られるものの、溶媒に用いたアルコールとアルカ
リ金属次亜塩素酸塩との反応から、爆発的に分解しやす
い不安定な次亜塩素酸エステルが形成されるため、危険
を伴う点で工業的規模の実施には適していない。Although the latter method yields benzofurazan-1-oxide in high yield, hypochlorous acid is unstable and easily decomposes explosively due to the reaction between the alcohol used as a solvent and the alkali metal hypochlorite. Due to the formation of esters, it is dangerous and therefore unsuitable for industrial scale implementation.
特開昭５６−７５４８０号公報には、トルエンのような
水不混和性有機溶媒と水からなる二層反応溶媒中に於い
て、相間移動触媒の存在下に、２−二トロアニリンとア
ルカリ金属塩を反応させて。JP-A-56-75480 discloses that 2-nitroaniline and an alkali metal salt are reacted in a two-layer reaction solvent consisting of a water-immiscible organic solvent such as toluene and water in the presence of a phase transfer catalyst. Let me react.
ベンゾフラザン−１−オキシドを製造する方法が開示さ
れている。しかし、この方法は高価な相間移動触媒を使
用しなければならず、また本発明者等の追試によれば、
高反応率を得るためには反応に約７時間もの長時間を要
し、しかも反応終了後は水と有機溶媒が混在する中間層
が形成されるため、分液が難しいと言う不都合があた。A method of making benzofurazan-1-oxide is disclosed. However, this method requires the use of an expensive phase transfer catalyst, and according to additional experiments by the present inventors,
In order to obtain a high reaction rate, the reaction requires a long time of about 7 hours, and after the reaction, an intermediate layer containing a mixture of water and organic solvent is formed, making it difficult to separate the liquids. .
Ｍｅｔｈｏｄｅｎ ｄｅｒ Ｏｒｇａｎｉｓｃｈｅｎ
Ｃｈｅｍｉｅ Ｓｔｉｃｋ−ｓｔｏｆｆ−Ｖｅｒｂｉｎ
ｄｕｎｇｅｎ １．Ｂａｎｄ Ｘ／ＴＥＩＬ １，１０
５８頁には、２−ニトロアニリンを水溶媒に懸濁させ。Methoden der Organischen
Chemie Stick-stoff-Verbin
dungeon 1. Band X/TEIL 1,10
On page 58, 2-nitroaniline is suspended in an aqueous solvent.
これを高速攪拌しながらアルカリ金属次亜塩素酸塩で酸
化する方法は記載されている。しかしながら、この方法
を本発明者等が追試してみたところによれば、ベンゾフ
ラザン−１−オキシドを高収率で取得すべく反応率を高
めると、たとえ高速攪拌を行なっていても反応液の分散
状態が徐々に悪化し、反応終了時には生成したベンゾフ
ラザン−１−オキシドが反応液表面に浮上して反応液は
流動性を失い、ベンゾフラザン−ｌ−オキシドの回収が
行なわれる次の濾過工程への移送さえ不可能になること
を突き止めた。従って、この方法も工業的規模での実施
には適していないと言える。A method of oxidizing this with an alkali metal hypochlorite while stirring at high speed has been described. However, when the present inventors conducted a follow-up test of this method, it was found that if the reaction rate was increased to obtain benzofurazan-1-oxide in a high yield, the reaction solution would be dispersed even with high-speed stirring. The condition gradually deteriorates, and at the end of the reaction, the generated benzofurazan-1-oxide floats to the surface of the reaction solution and the reaction solution loses fluidity, and is transferred to the next filtration step where benzofurazan-1-oxide is recovered. I found out that even that would be impossible. Therefore, it can be said that this method is also not suitable for implementation on an industrial scale.
［発明が解決しようとする問題点］
本発明は上述した従来技術の中にあって、水を反応溶媒
として２−ニトロアニリンをアルカリ金属次亜塩素酸塩
で酸化する方法の改良を目指すものであって１反応率を
高めた場合に反応液の分散状態が悪化して、ベンゾフラ
ザン−１−オキシドの回収が実質的に不可能になると言
う従来技術の問題点を解消せんとするものである。[Problems to be Solved by the Invention] The present invention aims to improve the method of oxidizing 2-nitroaniline with an alkali metal hypochlorite using water as a reaction solvent in the above-mentioned prior art. This is an attempt to solve the problem of the prior art in that when the 1 reaction rate is increased, the dispersion state of the reaction solution deteriorates, making it virtually impossible to recover benzofurazan-1-oxide.
［問題点を解決するための手段］
本発明の方法は、水を反応溶媒として前記した式（１）
で示される２−ニトロアニリン又はその誘導体を、強ア
ルカリ性条件下にアルカリ金属次亜塩素酸塩にて酸化し
て、前記の式（ＩＩ）で示されるベンゾフラザン−１−
オキシド又はその誘導体を製造する方法に於いて、反応
溶媒中に界面活性剤を共存させることを特徴とする。[Means for solving the problems] The method of the present invention is based on the above-mentioned formula (1) using water as a reaction solvent.
2-nitroaniline or a derivative thereof represented by the formula (II) is oxidized with an alkali metal hypochlorite under strongly alkaline conditions to produce benzofurazan-1- represented by the above formula (II).
The method for producing an oxide or a derivative thereof is characterized in that a surfactant is present in the reaction solvent.
［作 用］
水を反応溶媒として２−ニトロアニリン又はその誘導体
をアルカリ金属次亜塩素酸塩で酸化する反応の最大の問
題点は、既述した通り、反応の進行に伴って分散質の分
散状態が悪化し、特に反応生成物の反応溶媒に於ける分
散状態が悪化して生成物を含む反応混合物が流動性を失
うことにある。[Function] As mentioned above, the biggest problem with the reaction of oxidizing 2-nitroaniline or its derivatives with alkali metal hypochlorite using water as the reaction solvent is the dispersion of the dispersoids as the reaction progresses. Conditions deteriorate, especially the dispersion state of the reaction product in the reaction solvent deteriorates, and the reaction mixture containing the product loses fluidity.
上に示した式（Ｉ）及び（ｎ）の置換基Ｒがそれぞれ水
素である場合を例にとって界面活性剤の作用を説明する
と、本発明の方法で使用される界面活性剤は、原料２−
ニトロアニリン及び生成物ベンゾフラザン−１−オキシ
ドの水溶媒中での分散状態を良好に維持し、上記の如き
問題の発生を抑止する。従って１本発明では２−ニトロ
アニリン及びベンゾフラザン−１−オキシドの水中での
分散に優れた効果を発揮する界面活性剤がいずれも使用
可能であるが、典型的にはスルホン酸塩型又は硫酸エス
テル型などの陰イオン性界面活性剤が使用され、なかで
も分散能に優れ。To explain the action of the surfactant using the case where the substituents R in formulas (I) and (n) shown above are each hydrogen, the surfactant used in the method of the present invention is
The dispersion state of nitroaniline and the product benzofurazan-1-oxide in an aqueous solvent is maintained well, and the occurrence of the above-mentioned problems is suppressed. Therefore, in the present invention, any surfactant that exhibits an excellent effect on dispersing 2-nitroaniline and benzofurazan-1-oxide in water can be used, but typically a sulfonate type or a sulfuric acid ester is used. Anionic surfactants such as molds are used, especially those with excellent dispersion ability.
起泡性が少ない点で、硫酸エステル型陰イオン性界面活
性剤の使用が推奨される。界面活性剤の使用量は、反応
に供する原料２−ニトロアニリンの重量基準で０．０１
〜１．０ｗｔ％、好ましくは０．１〜０．５ｗｔ％の範
囲にある。The use of sulfate ester type anionic surfactants is recommended due to their low foaming properties. The amount of surfactant used is 0.01 based on the weight of the raw material 2-nitroaniline to be subjected to the reaction.
~1.0 wt%, preferably 0.1-0.5 wt%.
アルカリ金属次亜塩素酸塩としては、従来技術で使用さ
れるものが本発明でも使用することができるが、特に次
亜塩素酸ナトリウム及び次亜塩素酸カリウムが好ましい
。As the alkali metal hypochlorite, those used in the prior art can also be used in the present invention, but sodium hypochlorite and potassium hypochlorite are particularly preferred.
反応は従来技術と同様、強アルカリ性条件下で、典型的
にはｐｉ（１２以上の条件下で進められ、反応温度は一
１０〜５０℃、好ましくは２０〜４０℃の範囲で選択さ
れる０反応時間は長くても４時間程度で工業的に満足で
きる反応率と収率を上げることができる。As in the prior art, the reaction is carried out under strongly alkaline conditions, typically pi (12 or higher), and the reaction temperature is selected in the range of -10 to 50°C, preferably 20 to 40°C. An industrially satisfactory reaction rate and yield can be achieved with a reaction time of about 4 hours at most.
以上は２−ニトロアニリンを原料として、ベンゾフラザ
ン−１−オキシドを製造する場合を例にとって、本発明
の方法を詳述したが１式（２）に包含される２−ニトロ
アニリン誘導体から、式（ｎ）に包含されるベンゾフラ
ザン−１−オキシド誘導体を製造する場合も、上とほぼ
同様な反応条件を採用して目的のベンゾフラザン−１−
オキシド誘導体を取得することができる。The method of the present invention has been described above in detail by taking as an example the case where benzofurazan-1-oxide is produced using 2-nitroaniline as a raw material. When producing benzofurazan-1-oxide derivatives included in n), almost the same reaction conditions as above are adopted to produce the desired benzofurazan-1-
Oxide derivatives can be obtained.
［実 施 例］
実施例
攪拌機、還流冷却器、滴下ロート及び温度計を備えた５
００ｍ１容の四つロフラスコに、２−ニトロアニリン４
１．Ｉｇ（０，２９８モル）、水９０ｇ及び界面活性剤
として、アルキル硫酸エステルソーダ塩〔第一工業製薬
■製の［モノゲンＧＪ） ０．１２ｇを仕込み、普通の
攪拌下（３００〜３５０ｒｐｍ）に４８ガの水酸化ナト
リウム水溶液１５．１ｇ（０，１８１モル）を添加して
内温を２５〜３０℃に保ちながら、２時間掛けて滴下ロ
ートから１３．０％の次亜塩素酸ナトリウム水溶液２２
０ｇ（０，３８４モル）を滴下した。[Example] Example 5 equipped with a stirrer, a reflux condenser, a dropping funnel and a thermometer
2-nitroaniline 4 in a 00ml four-bottle flask
1. Ig (0,298 mol), 90 g of water, and 0.12 g of alkyl sulfate sodium salt [Monogen GJ manufactured by Daiichi Kogyo Seiyaku ■] as a surfactant were added, and the mixture was stirred under normal stirring (300 to 350 rpm) for 48 hours. Adding 15.1 g (0,181 mol) of aqueous sodium hydroxide solution from Moth and keeping the internal temperature at 25 to 30°C, a 13.0% aqueous sodium hypochlorite solution 22 was added from the dropping funnel over a period of 2 hours.
0 g (0,384 mol) was added dropwise.
滴下終了後、さらに３５〜４０℃にて４時間反応せしめ
て室温迄冷却し、しかる後反応混合物を３５％の塩酸で
ｐＨ７に中和した０次に反応混合物を濾過してベンゾフ
ラザン−１−オキシドの結晶を水層から濾別した後、充
分に水洗を行なって含水ベンゾフラザン−１−オキシド
４１．３ｇを得た。After completion of the dropwise addition, the reaction was further carried out at 35-40°C for 4 hours, cooled to room temperature, and then the reaction mixture was neutralized to pH 7 with 35% hydrochloric acid.Then, the reaction mixture was filtered to obtain benzofurazan-1-oxide. The crystals were filtered from the aqueous layer and washed thoroughly with water to obtain 41.3 g of hydrous benzofurazan-1-oxide.
次いでこれを減圧乾燥して４０．１ｇの製品ベンゾフラ
ザン−１−オキシドを回収した。This was then dried under reduced pressure to recover 40.1 g of product benzofurazan-1-oxide.
こうして得られた製品の融点は６８〜７０℃であり、ガ
スクロマトグラフィーで分析したベンゾフラザン−１−
オキシドの純度は９９．０％、未反応２−ニトロアニリ
ン量は０．５％であった。理論収率は９９．０％である
。The melting point of the product thus obtained was 68-70°C, and benzofurazan-1-1 was analyzed by gas chromatography.
The purity of the oxide was 99.0%, and the amount of unreacted 2-nitroaniline was 0.5%. The theoretical yield is 99.0%.
比較例
界面活性剤の使用を省き、攪拌を普通の攪拌（３００〜
３５０ｒｐｍ）から高速攪拌（６５０〜７００ｒｐｍ）
に変更した以外は先の実施例と全く同様な操作を行なっ
たところ、次亜塩素酸ナトリウム水溶液の滴下終了後、
さらに３５〜４０℃にて４時間反応させた段階で１反応
混合物は流動性のない泥状物となった。Comparative Example The use of surfactant was omitted, and the stirring was carried out using normal stirring (300
350 rpm) to high speed stirring (650-700 rpm)
When the operation was exactly the same as in the previous example except that the change was made to
After a further 4 hours of reaction at 35 to 40°C, the reaction mixture turned into a slurry with no fluidity.
そこで、この反応混合物を匙で濾過具上に取り出し、塩
酸で中和後、充分水洗して含水ベンゾフラザン−１−オ
キシドを得た。次にこの含水物を減圧乾燥して３Ｌ１ｇ
の製品ベンゾフラザン−１−オキシドを回収した。この
ものの融点は６８〜７０℃であり、ガスクロマトグラフ
ィーで分析したベンゾフラザン−１−オキシドの純度は
９７．５％、未反応２−ニトロアニリン量は１．６％で
あった。Therefore, this reaction mixture was taken out onto a filter using a spoon, neutralized with hydrochloric acid, and thoroughly washed with water to obtain hydrous benzofurazan-1-oxide. Next, this water-containing material was dried under reduced pressure to produce 3L1g
The product benzofurazan-1-oxide was recovered. The melting point of this product was 68 to 70°C, the purity of benzofurazan-1-oxide analyzed by gas chromatography was 97.5%, and the amount of unreacted 2-nitroaniline was 1.6%.
理論収率は９４．２％である。The theoretical yield is 94.2%.
［発明の効果コ
本発明の方法では、原料及び反応生成物の分散に寄与す
る界面活性剤の共存下に１反応が進められるため、従来
法よりも反応率を高めることができ、また反応率を高め
た場合にも反応混合物が泥状化してしまうことがない。[Effects of the invention] In the method of the present invention, one reaction is carried out in the coexistence of a surfactant that contributes to the dispersion of raw materials and reaction products, so the reaction rate can be increased compared to conventional methods, and the reaction rate can also be increased. Even when the temperature is increased, the reaction mixture does not become muddy.
従って、本発明によれば所望の目的生成物を高収率で得
ることができる。また、本発明の方法は界面活性剤を使
用する関係で、生成物中に界面活性剤が若干混入するが
、その界面活性剤も生成物を充分水洗することによって
、除去することができる。さらに付は加えれば、本発明
の方法は水を溶媒としているため、アルコールを溶媒と
した場合の如く爆発の危険がなく、シかも反応終了後に
濾別される廃液は、界面活性剤を含むだけのアルカリ水
溶液であるので、排水処理も容易である。Therefore, according to the present invention, a desired target product can be obtained in high yield. Further, since the method of the present invention uses a surfactant, some surfactant is mixed into the product, but the surfactant can also be removed by thoroughly washing the product with water. Furthermore, since the method of the present invention uses water as a solvent, there is no risk of explosion unlike when alcohol is used as a solvent, and the waste liquid that is filtered out after the completion of the reaction only contains a surfactant. Since it is an alkaline aqueous solution, wastewater treatment is easy.
Claims (1)
学式、表等があります▼（II） 但し、Ｒは水素、ハロゲン、Ｃ＿１〜Ｃ＿４のアルキル
基又はＣ＿１〜Ｃ＿４のアルコキシ基を示す。 水を反応溶媒として上記の式（ I ）で示される２−ニ
トロアニリン又はその誘導体を、強アルカリ性条件下に
アルカリ金属次亜塩素酸塩にて酸化して上記の式（II）
で示されるベンゾフラザン−１−オキシド又はその誘導
体を製造する方法に於いて、反応溶媒中に界面活性剤を
共存させることが特徴とするベンゾフラザン−１−オキ
シド又はその誘導体の製造方法。 ２、前記の界面活性剤がスルホン酸塩型又は硫酸エステ
ル型の陰イオン性界面活性剤である特許請求の範囲第１
項記載の方法。[Claims] 1. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) However, R is hydrogen, halogen, an alkyl group of C_1 to C_4, or C_1 ~C_4 represents an alkoxy group. 2-nitroaniline or its derivative represented by the above formula (I) is oxidized with an alkali metal hypochlorite under strongly alkaline conditions using water as a reaction solvent to form the above formula (II).
A method for producing benzofurazan-1-oxide or a derivative thereof, characterized in that a surfactant is present in the reaction solvent. 2. Claim 1, wherein the surfactant is a sulfonate type or sulfate ester type anionic surfactant.
The method described in section.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22488986A JPS6383078A (en) | 1986-09-25 | 1986-09-25 | Production of benzofurazan-1-oxide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22488986A JPS6383078A (en) | 1986-09-25 | 1986-09-25 | Production of benzofurazan-1-oxide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6383078A true JPS6383078A (en) | 1988-04-13 |
Family
ID=16820749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22488986A Pending JPS6383078A (en) | 1986-09-25 | 1986-09-25 | Production of benzofurazan-1-oxide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6383078A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6248895B1 (en) * | 1998-05-22 | 2001-06-19 | Torrent Pharmaceuticals Ltd. | Benzofuroxan compound, method of preparation, pharmaceutical composition and method of treatment using the same |
-
1986
- 1986-09-25 JP JP22488986A patent/JPS6383078A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6248895B1 (en) * | 1998-05-22 | 2001-06-19 | Torrent Pharmaceuticals Ltd. | Benzofuroxan compound, method of preparation, pharmaceutical composition and method of treatment using the same |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5763650A (en) | Process for the preparation of a halosubstituted aromatic acid | |
| JPS6383078A (en) | Production of benzofurazan-1-oxide | |
| JP3789749B2 (en) | Method for producing thiosalicylic acid | |
| KR970011007B1 (en) | Hydroxyethylsulfonylnitro and hydroxyethylsulfonylamino-benozic acids and process for thier preparation | |
| US6274714B1 (en) | Method for producing 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride | |
| JPH10168027A (en) | Production of ruthenium (iii) acetate solution | |
| US6077941A (en) | Method for producing 1,2-naphthoquinone-2-diazide derivatives | |
| US4180513A (en) | Method for synthesizing acid blue 104 | |
| CN117447423A (en) | Preparation method of thiadiazolyl sulfonyl chloride compounds and thiadiazolyl sulfonamide compounds | |
| JPH0314557A (en) | Production of 4,4'-thiobisbenzene thiol | |
| JP2730991B2 (en) | Method for producing 1-amino-2-chloro-4-hydroxy-anthraquinone | |
| JP4031156B2 (en) | Preferential production method of Z form of 2-aminothiazole derivative | |
| KR100379637B1 (en) | Method for preparing 2-amino-3,5-dibromobenzaldehyde having high purity and yield | |
| JP3884572B2 (en) | Process for producing tert-butyl 4'-methyl-2-biphenylcarboxylate | |
| KR100517343B1 (en) | Preparation method of Methoxyphenylhydrazine | |
| JPH04273844A (en) | Preparation of 2,2'-oxydisuccinic acid salt | |
| JPS62167754A (en) | Production of cyanomethylthioacetic acids | |
| ZA200204875B (en) | Novel process of the preperation of alpha-(2-4-disulfophenyl)-N-tert-butylnitrone and pharmaceutically acceptable salts thereof. | |
| US4374989A (en) | Process for the manufacture of dianthraquinonyl-N,N'-dihydroazine | |
| RU1817772C (en) | Process for preparing 2-chloro-4-nitroaniline | |
| JP2614108B2 (en) | Method for producing sulfenyl oxime carbamate derivative | |
| JPS62255454A (en) | Production of 2-(4,4'-bis(dimethylamino)-benzohydryl)-5-dimethylaminobenz-oic acid | |
| JPS6042784B2 (en) | Method for producing 1-aminoanthraquinone | |
| JPS609033B2 (en) | Method for producing 3-hydroxy-5-phenyl isoxazole | |
| JPH10218856A (en) | Production of 4-sulfonamidophenylhydrazine hydrochloride |