JPS62181240A - Production of 2,6-dichloro-p-nitrophenol - Google Patents
Production of 2,6-dichloro-p-nitrophenolInfo
- Publication number
- JPS62181240A JPS62181240A JP2299586A JP2299586A JPS62181240A JP S62181240 A JPS62181240 A JP S62181240A JP 2299586 A JP2299586 A JP 2299586A JP 2299586 A JP2299586 A JP 2299586A JP S62181240 A JPS62181240 A JP S62181240A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- nitrophenol
- dichloro
- salt
- reaction
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- PXSGFTWBZNPNIC-UHFFFAOYSA-N 618-80-4 Chemical compound OC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl PXSGFTWBZNPNIC-UHFFFAOYSA-N 0.000 title abstract 2
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000000126 substance Substances 0.000 claims abstract description 9
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000002378 acidificating effect Effects 0.000 claims abstract description 7
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims abstract description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 15
- 150000003839 salts Chemical class 0.000 abstract description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 6
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract description 2
- 235000011054 acetic acid Nutrition 0.000 abstract description 2
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- 239000000975 dye Substances 0.000 abstract description 2
- 235000019253 formic acid Nutrition 0.000 abstract description 2
- 150000007522 mineralic acids Chemical class 0.000 abstract description 2
- 229910017604 nitric acid Inorganic materials 0.000 abstract description 2
- 150000007524 organic acids Chemical class 0.000 abstract description 2
- 239000000049 pigment Substances 0.000 abstract description 2
- 235000019260 propionic acid Nutrition 0.000 abstract description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 abstract description 2
- -1 Na salt Chemical class 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 abstract 1
- 238000000034 method Methods 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
- 229940005991 chloric acid Drugs 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は２．６−ジクロロ−Ｐ−ニトロフェノールの製
造法に関する。DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to a process for producing 2,6-dichloro-P-nitrophenol.
更に詳シくは、Ｐ−ニトロフェノールをジクロル化する
事による２、６−ジクロロ−Ｐ−ニトロフェノールの製
造法に関する。More specifically, the present invention relates to a method for producing 2,6-dichloro-P-nitrophenol by dichlorinating P-nitrophenol.
従来の技術 ２．６−シクロローＰ−ニトロフェノールハ。Conventional technology 2.6-cycloP-nitrophenol.
医薬、農薬あるいは染顔料用の原料として重要な化合物
である。２，６−ジクロロ−Ｐ−ニトロフェノールの製
法としては。It is an important compound as a raw material for medicines, agricultural chemicals, and dyes and pigments. As a method for producing 2,6-dichloro-P-nitrophenol.
（１） Ｐ−ニトロフェノールの水溶液に塩素を作用
させる方法（Ｂｓｉｌｅｔｅｉｎ ■２４１〜２頁）（
２）Ｐ−ニトロフェノールを塩酸と塩素酸ソーダで処理
する方法（ＦＢ−Ｒ６ｐＯｒ ｔ、 Ａ ７８１ ）（
５） 溶融状Ｐ−ニトロフェノールに塩素を作用させ
る方法（特開昭５７−７０８４０）（４） 塩化メチ
レン等を溶媒に、Ｐ−ニトロフェノールに塩素を反応さ
せる方法（特開昭５７−ｙａａａａ）
（５） ｍ塩酸中、Ｐ−ニトロフェノールに塩素全反
応させる方法（特開昭６Ｏ−５６９５９）（６）Ｐ−ニ
トロフェノールを濃塩酸と過酸化水素で処理する方法（
特開昭５７−６４６４６）等が提案されている。(1) Method of applying chlorine to an aqueous solution of P-nitrophenol (Bsiletein ■pages 241-2) (
2) Method of treating P-nitrophenol with hydrochloric acid and sodium chlorate (FB-R6pOrt, A 781) (
5) Method of reacting chlorine with molten P-nitrophenol (Japanese Unexamined Patent Publication No. 57-70840) (4) Method of reacting P-nitrophenol with chlorine using methylene chloride or the like as a solvent (Japanese Unexamined Patent Publication No. 57-yaaaa) (5) A method in which P-nitrophenol is subjected to a total chlorine reaction in m-hydrochloric acid (JP-A-6O-56959) (6) A method in which P-nitrophenol is treated with concentrated hydrochloric acid and hydrogen peroxide (
JP-A-57-64646) and the like have been proposed.
発明が解決しようとする問題点
前記し７’Ｃ２，６−ジクロロ−Ｐ−ニトロフェノール
の製法とじて公知の前記した製法はそれぞれ欠点がある
。即ち。Problems to be Solved by the Invention Each of the above-mentioned processes known as the process for preparing 7'C2,6-dichloro-P-nitrophenol has drawbacks. That is.
（１）の方法は溶解度の低いＰ−ニトロフェノールを極
めて希薄な溶液として反応させねばならない上樹脂状物
質を生成しやすく、収率も低い。In method (1), P-nitrophenol, which has low solubility, must be reacted as an extremely dilute solution, and resin-like substances are likely to be produced, and the yield is low.
（２）の方法は塩素酸ソーダを使用する為、このものの
取扱いに規制を受けるのみならず取扱いを誤ると反応中
に爆発の危険もある。Since method (2) uses sodium chlorate, not only is the handling of this substance subject to regulations, but there is also the risk of explosion during the reaction if handled incorrectly.
（５）の方法は、ｐ−ニトロフェノールが溶融時。Method (5) is when p-nitrophenol is melted.
分解する為工業的に有利な方法とはいいがたい。It is hard to say that it is an industrially advantageous method because it decomposes it.
（４）の方法は塩素を使用する為、その設備上の制約、
又、過剰の塩素を使用することに基づくオフガスの除害
設備の付与等、工業的に制約が大きい。Since method (4) uses chlorine, there are restrictions on the equipment,
Furthermore, there are significant industrial restrictions such as the provision of off-gas abatement equipment due to the use of excess chlorine.
（ｓ） （６）の方法は１反応率は高いものの反応中の
粘度が著しく高く、効率のよい工業的製法にはなりえな
い。(s) Although the method (6) has a high 1 reaction rate, the viscosity during the reaction is extremely high, and it cannot be an efficient industrial production method.
このような背景から操作が簡便で設備生産性のたかい方
法によって高収率、高純度で２．６−ジクｏ ｏ −Ｐ
−ニトロフェノールを製造する方法の開発が望まれてい
る。Against this background, 2,6-dichloro-P can be produced in high yield and purity using a method that is easy to operate and has high equipment productivity.
- It is desired to develop a method for producing nitrophenol.
問題点を解決する為の手段
本発明者は前記したような問題点を解決すべく鋭意研究
を重ねた結果１本発明に至ったものである。Means for Solving the Problems The present inventor has conducted extensive research to solve the above-mentioned problems, and as a result has arrived at the present invention.
即ち、本発明は、Ｐ−ニトロフェノールに次亜塩素酸又
は／及びその塩と酸性物質を作用させジクロル化する事
を特徴とする。２，６−ジクロロ−Ｐ−ニトロフェノー
ルの製造法を提供する。That is, the present invention is characterized in that P-nitrophenol is dichlorinated by reacting hypochlorous acid or/and a salt thereof with an acidic substance. A method for producing 2,6-dichloro-P-nitrophenol is provided.
本発明の方法を実施するにあたっては通常は。In carrying out the method of the invention, typically.
次亜塩素酸又は／及びその塩の水浴液中に、 ｐ −ニ
トロフェノールを加えた後、撹拌下に酸性物質の水溶液
を徐々に加えて反応を行うのが好ましく使用する次亜塩
素ハ又は／及びその塩としては次亜塩素ば又は、そのナ
トリウム塩、カリウム塩等のアルカリ金属の塩が挙げら
れるが、これらは混合物として用いてもよくこれらは通
常水浴液として用いられる。その濃度については特に制
限はないが１例えば次亜塩素酸ナトリウムを用いる場合
には工業的入手の容易性１倫格等を考慮し、市販の１０
〜１４重量％濃度のものを使用するのが有利である。そ
の使用量は原料（ｐ−ニトロフェノール）１モルに対し
て４．０〜６．５モル好ましくは４．５〜５．５モルで
ある。After adding p-nitrophenol to a water bath solution of hypochlorous acid or/and its salt, it is preferable to carry out the reaction by gradually adding an aqueous solution of an acidic substance under stirring. Examples of the salts thereof include hypochlorite, and salts of alkali metals such as sodium salts and potassium salts thereof, but these may be used as a mixture, and these are usually used as a water bath solution. There are no particular restrictions on the concentration, but for example, when using sodium hypochlorite, commercially available 10
Advantageously, a concentration of ~14% by weight is used. The amount used is 4.0 to 6.5 mol, preferably 4.5 to 5.5 mol, per 1 mol of the raw material (p-nitrophenol).
又１本発明の方法で使用する酸性物質としては塩ば、硫
酸、硝酸、リン酸等の無機酸、蟻酸、酢酸、プロピオン
酸、酪酸等の有機酸を挙げることが出来る。これらは使
用する次亜塩素酸又は／及び塩に対して０．４〜０．６
５等量モル好ましくは０．５〜０．６等量モル使用され
１通常これらを水で希釈し３０〜７０重ｆｆｉ％水溶液
として使用する。The acidic substances used in the method of the present invention include salts, inorganic acids such as sulfuric acid, nitric acid and phosphoric acid, and organic acids such as formic acid, acetic acid, propionic acid and butyric acid. These are 0.4 to 0.6 based on the hypochlorous acid or/and salt used.
5 equivalent moles, preferably 0.5 to 0.6 equivalent moles, are used.1 Usually, these are diluted with water and used as a 30 to 70 weight percent aqueous solution.
反応温度については、−１０℃〜１００℃、好ましくは
１５℃〜７０℃で実施するのが良い。The reaction temperature is preferably -10°C to 100°C, preferably 15°C to 70°C.
これより温度が低い場合は、反応速度が低下するととも
に、好ましくない副生物を生じる。又これより高い温度
で反応を実施した場合には次亜塩素酸の分解による塩素
化剤の損失、及び酸化反応の銹発による酸化性副生物を
生じて、収率１品質の低下を来すので好ましくない。Lower temperatures will reduce the reaction rate and produce undesirable by-products. If the reaction is carried out at a temperature higher than this, the loss of the chlorinating agent due to the decomposition of hypochlorous acid and the generation of oxidizing by-products due to the rusting of the oxidation reaction will result in a decrease in yield and quality. So I don't like it.
このようにして、１〜６時間反応させることによって反
応を終了し通常反応液を酸性化してから目的物を結晶と
して分離する。このようにして。In this way, the reaction is completed by reacting for 1 to 6 hours, and the reaction solution is usually acidified and then the target product is separated as crystals. In this way.
純反９５％以上、収率８０％以上で、目的とする２、６
−ジクロロ−Ｐ−ニトロフェノールを得る。Purity 95% or more, yield 80% or more, target 2, 6
-dichloro-P-nitrophenol is obtained.
なお更に高純度の目的物を得る為に、一般的な精製手段
（例えば再結晶）を施すことも出来る。Furthermore, in order to obtain the target product with even higher purity, general purification means (for example, recrystallization) can also be applied.
実施例 本発明を実施例によって、更に詳細に説明する。Example The present invention will be explained in more detail by way of examples.
実施例１
撹拌機、温度計、冷却管及び滴下ロートを備えた５ｔの
四ツロフラスコに、１５３重量％濃度の次亜塩素酸ナト
リウム（ＮａＣ１０）水浴液３．５ｔ。Example 1 3.5 t of sodium hypochlorite (NaC10) water bath solution with a concentration of 153% by weight was placed in a 5 t four-ton flask equipped with a stirrer, a thermometer, a condenser and a dropping funnel.
Ｐ−ニトロフェノール２ ＋ ２．４９を加えた後。After adding P-nitrophenol 2 + 2.49.
２０〜５０℃にて、Ｓ塩酸４５７ｔと水４５７ノ応温度
が５０℃を越えない様にした。塩酸の滴下終了時、はぼ
反応は完了したが尚１５分間攪拌を続けた後、反応液を
高速液体クロマトグラフィーで分析すると、目的物の生
成率は９５％であった。At 20 to 50°C, the reaction temperature of 457 tons of S hydrochloric acid and 457 tons of water was made not to exceed 50°C. At the end of the dropwise addition of hydrochloric acid, the reaction was completed; however, stirring was continued for 15 minutes, and the reaction solution was analyzed by high performance liquid chromatography, and the yield of the target product was 95%.
この反応液に、濃塩酸９０ゴを加え敵性とした後、２０
〜３０℃に於いて生成物をＰ別した。この結晶を真空乾
燥し２７０２の目的物（２，６−ジクロロ−Ｐ−ニトロ
フェノール）ｅ？４１ｃ。After adding 90 grams of concentrated hydrochloric acid to this reaction solution to make it hostile, 20 grams of concentrated hydrochloric acid was added to make it hostile.
The product was separated from P at ~30°C. The crystals were dried under vacuum to produce the desired product of 2702 (2,6-dichloro-P-nitrophenol) e? 41c.
この目的物を高速液体クロマトグラフィーで分析した結
果、純度は９７．９％であった。As a result of analyzing this target product by high performance liquid chromatography, the purity was found to be 97.9%.
（参考実験）
実施例１でえられた２、６−ジクロロ−Ｐ−ニトロフェ
ノールをベシャン還元法で反応させた結果２．６−ジク
ロロ−Ｐ−アミンフェノールが収率８５％で得られた。(Reference experiment) As a result of reacting the 2,6-dichloro-P-nitrophenol obtained in Example 1 by the Bechamp reduction method, 2,6-dichloro-P-aminephenol was obtained in a yield of 85%.
実施例２〜５
実施例１に準じて下記表に示される反応条件によって反
応を実施しそれぞれ「結果」で示されるような収率、純
度で２，６−ジクロロ−Ｐ−ニトロフェノール金、ｔだ
。Examples 2 to 5 The reaction was carried out according to the reaction conditions shown in the table below according to Example 1, and 2,6-dichloro-P-nitrophenol gold, t is.
注（１） Ｎａ０Ｃ１（＋ ３．３重ｔ％水溶ｏ、）
はＰ−ニトロフェノール１ｍ０１に対する使用量（２）
酸（酸性物質）はそれぞれ同重漬の水と混合した上
で使用した。Note (1) Na0C1 (+3.3wt% water soluble o,)
is the amount used per 1 m01 of P-nitrophenol (2)
Each acid (acidic substance) was mixed with the same amount of water before use.
発明の効果
Ｐ−ニトロフェノールヲシクロル化り、ＬＡ−ジクロロ
−Ｐ−ニトロフェノールを製造する方法において１次組
塩素酸又は／及びその塩を使用して安全で、かつ効率的
な方法によって高純度。Effects of the invention In the method of producing LA-dichloro-P-nitrophenol by cyclolating P-nitrophenol, it is possible to obtain high purity by a safe and efficient method using primary chloric acid or/and its salts. .
高収率で２．６−シクロローＰ−ニトロフェノールを製
造する事が出来る様になった。It became possible to produce 2,6-cyclop-nitrophenol in high yield.
Claims (1)
次亜塩素酸塩と酸性物質を作用させる事を特徴とする２
，６−ジクロロ−Ｐ−ニトロフェノールの製造法(1) 2 characterized by the action of hypochlorous acid or/and hypochlorite and an acidic substance on P-nitrophenol.
, 6-dichloro-P-nitrophenol manufacturing method
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2299586A JPS62181240A (en) | 1986-02-06 | 1986-02-06 | Production of 2,6-dichloro-p-nitrophenol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2299586A JPS62181240A (en) | 1986-02-06 | 1986-02-06 | Production of 2,6-dichloro-p-nitrophenol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62181240A true JPS62181240A (en) | 1987-08-08 |
| JPH0220621B2 JPH0220621B2 (en) | 1990-05-10 |
Family
ID=12098106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2299586A Granted JPS62181240A (en) | 1986-02-06 | 1986-02-06 | Production of 2,6-dichloro-p-nitrophenol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62181240A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111440072A (en) * | 2020-04-08 | 2020-07-24 | 江苏扬农化工集团有限公司 | Synthetic method of chlorfluazuron key intermediate 2, 6-dichloro-4-nitrophenol |
-
1986
- 1986-02-06 JP JP2299586A patent/JPS62181240A/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111440072A (en) * | 2020-04-08 | 2020-07-24 | 江苏扬农化工集团有限公司 | Synthetic method of chlorfluazuron key intermediate 2, 6-dichloro-4-nitrophenol |
| CN111440072B (en) * | 2020-04-08 | 2022-12-13 | 江苏扬农化工集团有限公司 | Synthetic method of chlorfluazuron key intermediate 2, 6-dichloro-4-nitrophenol |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0220621B2 (en) | 1990-05-10 |
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