JPS6140215B2 - - Google Patents
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- Publication number
- JPS6140215B2 JPS6140215B2 JP13705779A JP13705779A JPS6140215B2 JP S6140215 B2 JPS6140215 B2 JP S6140215B2 JP 13705779 A JP13705779 A JP 13705779A JP 13705779 A JP13705779 A JP 13705779A JP S6140215 B2 JPS6140215 B2 JP S6140215B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- acid
- water
- tca
- hydrochloric acid
- 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.)
- Expired
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- 239000007864 aqueous solution Substances 0.000 claims description 8
- NATVSFWWYVJTAZ-UHFFFAOYSA-N 2,4,6-trichloroaniline Chemical compound NC1=C(Cl)C=C(Cl)C=C1Cl NATVSFWWYVJTAZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 5
- BEHLMOQXOSLGHN-UHFFFAOYSA-N benzenamine sulfate Chemical class OS(=O)(=O)NC1=CC=CC=C1 BEHLMOQXOSLGHN-UHFFFAOYSA-N 0.000 description 5
- 235000010265 sodium sulphite Nutrition 0.000 description 5
- IMUUNYPYNWXUBO-UHFFFAOYSA-N 4-aminobenzene-1,3-disulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1S(O)(=O)=O IMUUNYPYNWXUBO-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 4
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229950000244 sulfanilic acid Drugs 0.000 description 3
- KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 2
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 2
- ZKQDCIXGCQPQNV-UHFFFAOYSA-N Calcium hypochlorite Chemical compound [Ca+2].Cl[O-].Cl[O-] ZKQDCIXGCQPQNV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- IQWHOYGEJQVUAU-UHFFFAOYSA-N O(Cl)Cl.[Cl] Chemical compound O(Cl)Cl.[Cl] IQWHOYGEJQVUAU-UHFFFAOYSA-N 0.000 description 2
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- OSKPFQZATUQPEE-UHFFFAOYSA-M [Cl+].[O-]Cl(=O)=O Chemical compound [Cl+].[O-]Cl(=O)=O OSKPFQZATUQPEE-UHFFFAOYSA-M 0.000 description 2
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- SAUMVKNLVQDHMJ-UHFFFAOYSA-N dichlorine trioxide Inorganic materials ClOCl(=O)=O SAUMVKNLVQDHMJ-UHFFFAOYSA-N 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- GVPODVKBTHCGFU-UHFFFAOYSA-N 2,4,6-tribromoaniline Chemical compound NC1=C(Br)C=C(Br)C=C1Br GVPODVKBTHCGFU-UHFFFAOYSA-N 0.000 description 1
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
２，４，６―トリクロルアニリン（以下TCA
と略称する）は染料、顔料、及び農薬等の中間体
として重要であり、種々の製造法が提案されてい
る。[Detailed description of the invention] 2,4,6-trichloroaniline (hereinafter referred to as TCA)
) is important as an intermediate for dyes, pigments, and agricultural chemicals, and various production methods have been proposed.
例えば、クロロホルム中のアニリン塩酸塩に塩
素ガスを通じる方法（Chattaway，Irving，
Journal of the Chemical Society.London 1933
巻、142ページ）、
アニリンの四塩化炭素溶液を塩素化する方法
（DaVies，Journal of the Chemical Society.
London1927巻 1123ページ）、
ベンゼンの存在下でアニリン塩酸塩をスルフリ
ルクロライドで処理する方法（Eller，Klemm，
Berichte der Deutschen Chemischen
Gesellschaft 55巻 221ページ）、
アニリンを10倍量の二硫化炭素に溶解し、乾燥
酸素ガスを通じる（V.Meyer，Sudborough、
Berichte der Deutschen Chemischen
Gesellschaft 27巻 3151ページ）、
２，４―ジクロルアニリンを塩酸中塩素により
酸素化する（Reed、Orton、Journal of the
Chemical Society.London91巻 1553ページ）、
２，４，６―トリブロムアニリンを濃塩酸と
200〜240℃に加熱する（Wegscheider，
Monatocheftefiir Chemie18巻333ページ）等であ
る。 For example, passing chlorine gas through aniline hydrochloride in chloroform (Chattaway, Irving,
Journal of the Chemical Society.London 1933
(Vol., p. 142), Method for Chlorinating Aniline in Carbon Tetrachloride Solutions (DaVies, Journal of the Chemical Society.
(London 1927, p. 1123), Treatment of Aniline Hydrochloride with Sulfuryl Chloride in the Presence of Benzene (Eller, Klemm,
Berichte der Deutschen Chemischen
Gesellschaft, Vol. 55, p. 221), aniline is dissolved in 10 times the amount of carbon disulfide, and dry oxygen gas is passed through it (V. Meyer, Sudborough,
Berichte der Deutschen Chemischen
Oxygenation of 2,4-dichloroaniline with chlorine in hydrochloric acid (Reed, Orton, Journal of the
(Chemical Society.London Vol. 91, p. 1553), 2,4,6-tribromoaniline with concentrated hydrochloric acid.
Heat to 200-240℃ (Wegscheider,
Monatocheftefiir Chemie Vol. 18, p. 333), etc.
しかし、何れの方法も高価な有機溶剤や塩素化
剤を使用したり、出発原料が既に入手が容易でな
い（２，４―ジクロルアニリン）等の理由で、工
業的には実施困難な方法である。 However, both methods are difficult to implement industrially because they use expensive organic solvents and chlorinating agents, and the starting material is not easily available (2,4-dichloroaniline). be.
本発明者はTCAの工業的製造法を研究した結
果、
一般式（）
（式中、Ａ及びＢはスルホン基又は水素原子を
表わし、Ａ，Ｂのうち少なくとも一つはスルホン
基を示す。）で示されるアニリンスルホン酸類を
無機強酸水溶液中で塩素化することを特徴とする
２，４，６―トリクロルアニリンの製造法を完成
した。 As a result of researching the industrial production method of TCA, the inventor found that the general formula () (wherein A and B represent a sulfonic group or a hydrogen atom, and at least one of A and B represents a sulfonic group) is chlorinated in an aqueous solution of a strong inorganic acid. We have completed a method for producing 2,4,6-trichloroaniline.
本発明の方法は原料が安価なアニリンスルホン
酸類で、之を無機強酸水溶液中で塩素化するとい
う簡単な方法である故、実施容易で、且つ得られ
るTCAの純度、収率共に満足すべきもので工業
的価値が高い。 The method of the present invention uses inexpensive aniline sulfonic acids as raw materials and is a simple method of chlorinating them in a strong inorganic acid aqueous solution, so it is easy to implement and the resulting TCA has satisfactory purity and yield. High industrial value.
アニリンスルホン酸類としてはスルフアニル
酸、オルタニル酸、２，４―アニリンジスルホン
酸がある。 Aniline sulfonic acids include sulfanilic acid, orthanilic acid, and 2,4-anilinedisulfonic acid.
無機強酸としては塩酸又は硫酸等が使用でき
る。無機強酸水溶液として塩酸を用いる場合、塩
酸の濃度が10％以上のものが好ましい。塩酸は濃
度の高い方が好ましく、特に35％以上の濃塩酸が
好ましい。 Hydrochloric acid, sulfuric acid, etc. can be used as the inorganic strong acid. When using hydrochloric acid as the inorganic strong acid aqueous solution, the concentration of hydrochloric acid is preferably 10% or more. The higher the concentration of hydrochloric acid, the more preferable it is, and particularly preferable is concentrated hydrochloric acid of 35% or more.
硫酸を用いる場合、無機強酸水溶液としては20
〜85％の濃度の硫酸水溶液が好ましく、特に65〜
80％の濃度の硫酸水溶液が好ましい。 When using sulfuric acid, the inorganic strong acid aqueous solution is 20
Aqueous sulfuric acid solutions with a concentration of ~85% are preferred, especially 65~
An aqueous sulfuric acid solution with a concentration of 80% is preferred.
無機強酸水溶液はアニリンスルホン酸類の６〜
20重量倍用いるのが好ましい。 The inorganic strong acid aqueous solution contains 6 to 6 aniline sulfonic acids.
It is preferable to use 20 times the amount by weight.
塩素化は塩素ガスか、塩素の酸素酸塩と塩酸の
組合せで行なわれる。塩素の塩素酸塩としては、
例えば、次亜塩素酸ソーダ、次亜塩素酸カルシウ
ム、塩素酸ソーダ、又は塩素酸カリ等がある。塩
素の酸素酸塩の好ましい使用量は、次亜塩素酸塩
を用いる場合はアニリンスルホン酸類に対し次亜
塩素酸塩を４モル倍以下の範囲内で用いるのが好
ましく、塩素酸塩を用いる場合は、アニリンスル
ホン酸類に対し塩素酸塩を1.5モル倍以下の範囲
内で用いるのが好ましい。 Chlorination is carried out with chlorine gas or a combination of chlorine oxychloride and hydrochloric acid. As chlorine chlorate,
Examples include sodium hypochlorite, calcium hypochlorite, sodium chlorate, and potassium chlorate. The preferred usage amount of the chlorine oxychloride is that when using hypochlorite, it is preferably used within a range of 4 times the mole or less of hypochlorite to aniline sulfonic acids, and when using chlorate It is preferable to use the chlorate in an amount of 1.5 times or less by mole relative to the aniline sulfonic acid.
塩素化は−10℃から80℃までの範囲の温度で行
なうのが好ましく、特に−10〜10℃の温度で行な
うのが好ましい。 The chlorination is preferably carried out at a temperature in the range -10°C to 80°C, particularly preferably -10 to 10°C.
塩素化に要する時間は反応容器の形態、撹拌の
速さと効率、塩素ガスを通じる速度、或いは塩素
の塩素酸塩と塩酸の組合せで行う場合は酸素酸塩
の過剰度により異なるが普通１時間ないし３時間
で充分である。 The time required for chlorination varies depending on the configuration of the reaction vessel, the speed and efficiency of stirring, the rate of passage of chlorine gas, or the degree of excess of oxychloride when using a combination of chlorine chlorate and hydrochloric acid, but it is usually from 1 hour to 1 hour. 3 hours is enough.
反応が終つた内容物は、先ず亜硫酸塩で過剰の
塩素を消却し、多量の水中か、又は稀アルカリ水
溶液に投ずれば白色〜灰白色の結晶が析出するか
ら濾別し、水洗乾燥すると融点77〜78℃のTCA
が得られる。 After the reaction, first remove excess chlorine with sulfite, then pour it into a large amount of water or a dilute alkaline aqueous solution to precipitate white to grayish white crystals, filter them out, wash with water and dry to obtain a melting point of 77. TCA at ~78℃
is obtained.
ここに得られた化合物は例えばMethoden der
orgnischen chemie（Houben―Weyl）、BandV／
3Halogenverbindungen（1962年）884ページに記
載されているTCAの合成法により製出したTCA
と赤外吸収スペクトルは完全に一致し、又混融試
験では、融点降下を起さなかつた。 The compounds obtained here are e.g.
orgnischen chemie (Houben-Weyl), BandV/
3TCA produced by the TCA synthesis method described in Halogenverbindungen (1962) page 884
The infrared absorption spectra matched completely, and no drop in melting point occurred in the mixing test.
本発明の方法によればTCAを70％〜90％とい
う優れた収率で得ることができる。 According to the method of the present invention, TCA can be obtained with an excellent yield of 70% to 90%.
次に本発明を実施例により説明するが、文中部
とあるは何れも重量部を示す。 Next, the present invention will be explained with reference to Examples, where all parts in the text indicate parts by weight.
実施例 １
スルフアニル酸173部を36％塩酸1180部（1000
ml）中に加え充分撹拌する。全体を５〜０℃に冷
却し塩素ガスを約700c.c.／分の速度で３時間通じ
る。Example 1 173 parts of sulfanilic acid was mixed with 1180 parts of 36% hydrochloric acid (1000 parts
ml) and stir thoroughly. The whole is cooled to 5-0°C and chlorine gas is passed through it at a rate of about 700 c.c./min for 3 hours.
その後、亜硫酸ソーダ50部を300部の水に溶解
した溶液を添加して30分撹拌した後、更に水3000
c.c.／で稀釈する。 Then, a solution of 50 parts of sodium sulfite dissolved in 300 parts of water was added and stirred for 30 minutes, followed by an additional 3000 parts of water.
Dilute with cc/.
TCAが析出してくるから濾過し、得たケーキ
約300部を１％苛性ソーダ溶液1500部中に投じて
室温で撹拌し、濾過して充分に洗滌する。乾燥す
るとTCA170部が得られ、収率は86％である。 TCA precipitates out, so filter it. Approximately 300 parts of the resulting cake is poured into 1,500 parts of 1% caustic soda solution, stirred at room temperature, filtered, and thoroughly washed. After drying, 170 parts of TCA are obtained, with a yield of 86%.
実施例 ２
スルフアニル酸173部を36％塩酸2950部（2500
ml）中に懸濁して充分に撹拌する。内容物を０〜
５℃に冷却しておき、之に５％の活性塩素を含む
次亜塩素酸ソーダ溶液2200c.c.を２時間にわたつて
滴下する。Example 2 173 parts of sulfanilic acid was added to 2950 parts (2500 parts) of 36% hydrochloric acid.
ml) and stir thoroughly. Contents 0~
It was cooled to 5°C, and 2200 c.c. of sodium hypochlorite solution containing 5% active chlorine was added dropwise over 2 hours.
滴下終了後苛性ソーダ1200ｇを含んだ氷水3000
c.c.中に反応物を注加し、生成したTCAが充分に
析出したら、濾別し、水洗する。乾燥後TCAの
得量は138部であり、収率は70％であつた。 After dropping, add 3000 g of ice water containing 1200 g of caustic soda.
The reactant is poured into cc, and when the generated TCA is sufficiently precipitated, it is filtered and washed with water. The amount of TCA obtained after drying was 138 parts, and the yield was 70%.
実施例 ３
オルタニル酸173部を70％硫酸水溶液3000部中
に投じ、充分に撹拌しておく。外部より冷却し、
内温が５〜０℃になつたら塩素ガスを約800c.c.／
分の速度で３時間通じる。その後、亜硫酸ソーダ
の粉末60部を添加して30分撹拌した後、水8000部
中に反応物を注加してTCAを析出させる。これ
を濾過し、充分に水洗して乾燥する。Example 3 173 parts of ortanilic acid is poured into 3000 parts of a 70% sulfuric acid aqueous solution and stirred thoroughly. Cooled from the outside,
When the internal temperature reaches 5-0℃, add chlorine gas to about 800c.c./
It lasts 3 hours at the speed of a minute. Thereafter, 60 parts of sodium sulfite powder was added and stirred for 30 minutes, and then the reactant was poured into 8000 parts of water to precipitate TCA. This is filtered, thoroughly washed with water, and dried.
TCAの得量148部、収率75％である。 The amount of TCA obtained was 148 parts, a yield of 75%.
実施例 ４
オルタニル酸173部を36％塩酸2360部中に添加
し撹拌する。Example 4 173 parts of ortanilic acid is added to 2360 parts of 36% hydrochloric acid and stirred.
全体を０〜−５℃に冷却し、塩素酸ソーダの粉
末110部を少量ずつ２時間にわたつて添加する。
添加終了後、更に１時間撹拌してから過剰の塩素
を消却するために50部の亜硫酸ソーダを含む溶液
300部を加える。 The whole is cooled to 0 DEG to -5 DEG C. and 110 parts of sodium chlorate powder are added in small portions over a period of 2 hours.
After the addition is complete, stir for an additional hour and then add a solution containing 50 parts of sodium sulfite to quench the excess chlorine.
Add 300 copies.
30分撹拌してから6000部の水中に反応物を注入
し、濾過水洗する。乾燥後のTCAの得量は148部
で75％の収率である。 After stirring for 30 minutes, the reactant was poured into 6000 parts of water, filtered and washed with water. The amount of TCA obtained after drying was 148 parts, a yield of 75%.
実施例 ５
70％硫酸水溶液2500部に２，４―アニリンジス
ルホン酸253部を添加し、10〜５℃に冷却する。
酸素ガスを約900c.c.／分の速度で2.5時間通じる。Example 5 253 parts of 2,4-aniline disulfonic acid is added to 2500 parts of a 70% aqueous sulfuric acid solution, and the mixture is cooled to 10-5°C.
Oxygen gas is passed at a rate of about 900 c.c./min for 2.5 hours.
その後亜硫酸ソーダの粉末５部を加え30分撹拌
してから6000部の水中にあけ濾過し、充分に水
洗、乾燥する。TCAの得量は158部、80％の収率
である。 Then, add 5 parts of sodium sulfite powder, stir for 30 minutes, pour into 6,000 parts of water, filter, thoroughly wash with water, and dry. The amount of TCA obtained was 158 parts, a yield of 80%.
実施例 ６
２，４―アニリンジスルホン酸253部を36％塩
酸2950部（2500ml）中に懸濁して充分に撹拌す
る。これを−５〜−10℃に冷却し、活性塩素60％
を含む次亜塩素酸カルシウム200部に水100部を混
じた泥状液を２時間かかつて添加する。更に１時
間撹拌を続けてから6000部の水中に投じ、濾過、
水洗する。濾過ケーキは更に１％苛性ソーダ溶液
と室温で１時間撹拌してから、濾過水洗乾燥す
る。TCAの得量は163部、収率は83％である。Example 6 253 parts of 2,4-aniline disulfonic acid are suspended in 2950 parts (2500 ml) of 36% hydrochloric acid and thoroughly stirred. Cool this to -5 to -10℃ and use 60% active chlorine.
Add a slurry of 200 parts of calcium hypochlorite containing 100 parts of water for 2 hours or more. Continue stirring for another hour, then pour into 6000 parts of water, filter,
Wash with water. The filter cake is further stirred with 1% caustic soda solution for 1 hour at room temperature, then filtered, washed with water and dried. The amount of TCA obtained was 163 parts, and the yield was 83%.
実施例 ７
２，４―アニリンジスルホン酸253部を36％塩
酸2360部中に添加し充分に撹拌する。これを冷却
して０〜−５℃に達したら塩素酸カリの粉末123
部を少量ずつ２時間にわたつて添加する。添加終
了後、更に同温で１時間撹拌してから過剰の塩素
を消却するために50部の亜硫酸ソーダを含む溶液
300部を加える。30分撹拌してから6000部の水中
に反応物を注入し、濾過水洗する。濾過ケーキは
もう一度１％苛性ソーダ溶液で洗滌してから水洗
乾燥するTCAの得量は177部で収率は90％に達す
る。Example 7 253 parts of 2,4-aniline disulfonic acid are added to 2360 parts of 36% hydrochloric acid and thoroughly stirred. Cool this and when it reaches 0 to -5℃, powder of potassium chlorate 123
portion in small portions over 2 hours. After the addition is complete, stir for another hour at the same temperature, then add a solution containing 50 parts of sodium sulfite to eliminate excess chlorine.
Add 300 copies. After stirring for 30 minutes, the reactant was poured into 6000 parts of water, filtered and washed with water. The filter cake was washed once again with 1% caustic soda solution, then washed with water and dried.The amount of TCA obtained was 177 parts, and the yield reached 90%.
Claims (1)
表わし、Ａ，Ｂのうち少なくとも一つはスルホン
基を示す。）で示されるアニリンスルホン酸類を
無機強酸水溶液中で塩素化することを特徴とする
２，４，６―トリクロルアニリンの製造法。[Claims] 1 General formula () (wherein A and B represent a sulfonic group or a hydrogen atom, and at least one of A and B represents a sulfonic group) is chlorinated in an aqueous solution of a strong inorganic acid. A method for producing 2,4,6-trichloroaniline.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13705779A JPS5661334A (en) | 1979-10-25 | 1979-10-25 | Production of 2,4,6-trichloroaniline |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13705779A JPS5661334A (en) | 1979-10-25 | 1979-10-25 | Production of 2,4,6-trichloroaniline |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5661334A JPS5661334A (en) | 1981-05-26 |
| JPS6140215B2 true JPS6140215B2 (en) | 1986-09-08 |
Family
ID=15189871
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13705779A Granted JPS5661334A (en) | 1979-10-25 | 1979-10-25 | Production of 2,4,6-trichloroaniline |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5661334A (en) |
-
1979
- 1979-10-25 JP JP13705779A patent/JPS5661334A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5661334A (en) | 1981-05-26 |
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