JPS6140661B2 - - Google Patents
Info
- Publication number
- JPS6140661B2 JPS6140661B2 JP9097682A JP9097682A JPS6140661B2 JP S6140661 B2 JPS6140661 B2 JP S6140661B2 JP 9097682 A JP9097682 A JP 9097682A JP 9097682 A JP9097682 A JP 9097682A JP S6140661 B2 JPS6140661 B2 JP S6140661B2
- Authority
- JP
- Japan
- Prior art keywords
- acetyl
- sulfuric acid
- moles
- acid
- alkylacetophenone
- 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
Links
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 238000006277 sulfonation reaction Methods 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 2
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- FGIAPFAFWQPFOT-UHFFFAOYSA-N 5-acetyl-2-methylbenzenesulfonyl chloride Chemical compound CC(=O)C1=CC=C(C)C(S(Cl)(=O)=O)=C1 FGIAPFAFWQPFOT-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- FOBJXKVZKYRFOO-UHFFFAOYSA-N 5-acetyl-2-methylbenzenesulfonamide Chemical compound CC(=O)C1=CC=C(C)C(S(N)(=O)=O)=C1 FOBJXKVZKYRFOO-UHFFFAOYSA-N 0.000 description 1
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000008141 laxative Substances 0.000 description 1
- 229940125722 laxative agent Drugs 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical class NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 1
- -1 sodium 5-acetyl-2-methylbenzenesulfonate Chemical compound 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は、下記の構造式で表される５―アセチ
ル―２―アルキルベンゼンスルホン酸またはその
塩の製造法に関する。
The present invention relates to a method for producing 5-acetyl-2-alkylbenzenesulfonic acid or a salt thereof represented by the following structural formula.
【式】
（Ｒ：炭素数１ないし５のアルキル基、
Ｍ：水素原子またはアルカリ金属）
本発明の特徴は、下記反応式のごとく、４―ア
ルキルアセトフエノンに硫酸を配位させて硫酸コ
ンプレツクスを生成せしめ、低温でSO3を作用さ
せ選択的に５―アセチル―２―アルキルベンゼン
スルホン酸またはその塩を製造する方法である。
その作用機構は充分詳かではないが、スルホン
化反応において４―アルキルアセトフエノンに硫
酸を配位させることにより選択的に５―アセチル
―２―アルキルベンゼンスルホン酸またはその塩
を収率よく得ることができるのは画期的にすぐれ
た方法である。
４―アルキルアセトフエノンを濃硫酸を使用し
ないで無水硫酸または発煙硫酸と反応させるとア
セチル基がスルホン化され、５―アセチル―２―
アルキルベンゼンスルホン酸またはその塩はほと
んど得られない。
本発明のスルホン化に用いる濃硫酸は98％程度
のものを用い４―アルキルアセトフエノン１モル
に対し３〜15モル、望ましくは４〜８モル混合す
る。３モルより少ないと収率が低下し、15モル以
上を用いてもさしたる効果がないので不経済であ
る。
濃硫酸と混合した後に添加する無水硫酸もしく
は発煙硫酸中のSO3の量は４―アルキルアセトフ
エノン１モルに対し２〜15モル、望ましくは４〜
10モルが適当である。２モル未満では収率が低
く、15モル以上を超えてもさしたる効果がない。
この際の反応は20℃以下の低温で行なうのがよ
く、就中０〜10℃の範囲で行なうと好結果が得ら
れる。20℃を超えると収率が低下するので好まし
くなく、また０℃未満の低温は工業的実施に困難
を伴うので通常は０〜20℃の範囲で実施する。
本発明の反応はスルホン化に際し、４―アルキ
ルアセトフエノンのアセチル基に一且硫酸を配位
せしめて選択的に３の位置にスルホン化すること
により収率よく５―アセチル―２―アルキルベン
ゼンスルホン酸とその塩を得ることを特徴として
いる。
なお、本発明の方法に適用されるアルキル基と
しては、C1〜C5の低級アルキル基が一般に用い
られるが、その他アルコキシ基、アリール基など
の炭化水素を含む基にも広く利用できる。
本発明の物質である５―アセチル―２―アルキ
ルベンゼンスルホン酸またはその塩は種々の塩素
化反応、例えば塩化チオニルによる塩素化反応に
より心臟薬として知られているフエニルエタノー
ルアミン誘導体製造の中間体として有用な５―ア
セチル―２―アルキルベンゼンスルホニルクロラ
イドを高収率、高純度で製造することができる。
従来、５―アセチル―２―アルキルベンゼンス
ルホニルクロライドを製造する方法は、公知であ
り、いくつかの方法が文献に記載されている。
例えば、インデアンジヤーナル―オブケミスト
リイ（Indian.J.Chem.）18．271〜９（1976）に
は、４―メチルアセトフエノンをクロロホルム中
でクロルスルホン酸と加熱反応させて５―アセチ
ル―２―メチルベンゼンスルホニルクロライドを
得る方法が記載されているが、これから得られる
５―アセチル―２―メチルベンゼンスルホンアミ
ドの収率が30％と低いことから、低収率と推定さ
れる。
また、Ger.Offen.2，843，016，（1979）には、
３―アミノ―４―メチルアセトフエノンを低温で
ジアゾ化した後、氷酢酸中で塩化銅の存在下に亜
硫酸ガスを反応させて、５―アセチル―２―メチ
ルベンゼンスルホニルクロライドを製造する方法
が記されているが、原料が高価な上、低濃度の反
応であるため工業的には容積効率が悪く経済的な
方法ではない。
かかる目的のためには、本発明の方法で製造さ
れた５―アセチル―２―アルキルベンゼンスルホ
ン酸またはその塩を用いて容易に５―アセチル―
２―アルキルベンゼンスルホニルクロライドを高
収率で製造し得るからその工業的価値は極めて大
きい。
すなわち、本発明の５―アセチル―２―アルキ
ルベンゼンスルホン酸またはその塩は５―アセチ
ル―２―アルキルベンゼンスルホニクロライドお
よびその誘導体の原料として有用な物質である。
以上、本発明の化合物の製造および用途につい
て一般的に述べたが、さらに元素分析値、赤外吸
収スペクトル、NMRスペクトル、物理的性状を
掲げると共に製造について実施例をもつて具体的
に説明する。
＜実施例 １＞
98％硫酸530ｇ（5.3モル）中に４―メチルアセ
トフエノン134ｇ（1.0モル）を、15℃に保持しな
がら滴下し、30分間同温に保つて撹拌した。
次いで、５〜10℃に冷却しながら無水硫酸560
ｇ（7.0モル）を滴下した後、５℃に保つて５時
間撹拌を続けた。
水２に得られた反応液を添加して希釈した
後、45％水酸化ナトリウム水溶液2187ｇ（24.6モ
ル）を加えて中和した。中和後の反応液を60℃に
昇温した後、34℃まで徐冷して、生成した５―ア
セチル―２―メチルスルホン酸ナトリウムを晶析
させ取した。
収量は228.5ｇで純度は95％であり、収率は
92.0％であつた。
以下、実施例1.と同様の操作で第１表に示す量
を用いて反応せしめ第１表に示す結果を得た。[Formula] (R: Alkyl group having 1 to 5 carbon atoms, M: Hydrogen atom or alkali metal) The feature of the present invention is that, as shown in the reaction formula below, sulfuric acid complex is prepared by coordinating sulfuric acid to 4-alkylacetophenone. This is a method for selectively producing 5-acetyl-2-alkylbenzenesulfonic acid or its salt by producing Tx and reacting with SO 3 at low temperature. Although its mechanism of action is not fully understood, 5-acetyl-2-alkylbenzenesulfonic acid or its salt can be selectively obtained in good yield by coordinating sulfuric acid to 4-alkylacetophenone in the sulfonation reaction. This is an innovative and excellent method. When 4-alkyl acetophenone is reacted with anhydrous sulfuric acid or fuming sulfuric acid without using concentrated sulfuric acid, the acetyl group is sulfonated and 5-acetyl-2-
Almost no alkylbenzenesulfonic acid or its salt is obtained. The concentrated sulfuric acid used in the sulfonation of the present invention is about 98%, and is mixed in an amount of 3 to 15 moles, preferably 4 to 8 moles, per mole of 4-alkylacetophenone. When the amount is less than 3 moles, the yield decreases, and even when 15 moles or more is used, there is no significant effect and it is uneconomical. The amount of SO 3 in anhydrous sulfuric acid or oleum added after mixing with concentrated sulfuric acid is 2 to 15 mol, preferably 4 to 15 mol, per 1 mol of 4-alkylacetophenone.
10 moles is suitable. If it is less than 2 moles, the yield will be low, and if it exceeds 15 moles, there will be no significant effect. The reaction at this time is preferably carried out at a low temperature of 20°C or lower, and particularly good results are obtained when carried out at a temperature in the range of 0 to 10°C. If the temperature exceeds 20°C, the yield will decrease, which is not preferable, and if the temperature is lower than 0°C, it will be difficult to carry out industrially, so it is usually carried out at a temperature in the range of 0 to 20°C. The reaction of the present invention involves selectively sulfonating 5-acetyl-2-alkylbenzene sulfonate in high yield by coordinating mono- and sulfuric acid to the acetyl group of 4-alkylacetophenone and selectively sulfonating the 3-position. It is characterized by obtaining acids and their salts. Note that as the alkyl group applied to the method of the present invention, a lower alkyl group of C1 to C5 is generally used, but other groups containing hydrocarbons such as an alkoxy group and an aryl group can also be widely used. The substance of the present invention, 5-acetyl-2-alkylbenzenesulfonic acid or its salt, can be used as an intermediate in the production of phenylethanolamine derivatives, which are known as laxatives, by various chlorination reactions, such as chlorination reactions with thionyl chloride. Useful 5-acetyl-2-alkylbenzenesulfonyl chloride can be produced with high yield and high purity. Conventionally, methods for producing 5-acetyl-2-alkylbenzenesulfonyl chloride are known, and several methods are described in the literature. For example, Indian Journal of Chemistry (Indian.J.Chem.) 18 . 271-9 (1976) describes a method of heating and reacting 4-methylacetophenone with chlorosulfonic acid in chloroform to obtain 5-acetyl-2-methylbenzenesulfonyl chloride. Since the yield of 5-acetyl-2-methylbenzenesulfonamide is as low as 30%, it is assumed that the yield is low. Also, in Ger. Offen. 2, 843, 016, (1979),
There is a method for producing 5-acetyl-2-methylbenzenesulfonyl chloride by diazotizing 3-amino-4-methylacetophenone at low temperature and then reacting it with sulfur dioxide gas in the presence of copper chloride in glacial acetic acid. However, since the raw materials are expensive and the reaction is carried out at low concentrations, it is not an economical method because it is industrially inefficient in terms of volume. For this purpose, 5-acetyl-2-alkylbenzenesulfonic acid or its salt produced by the method of the present invention can be used to easily convert 5-acetyl-
Since 2-alkylbenzenesulfonyl chloride can be produced in high yield, its industrial value is extremely large. That is, the 5-acetyl-2-alkylbenzenesulfonic acid or its salt of the present invention is a substance useful as a raw material for 5-acetyl-2-alkylbenzenesulfonichloride and its derivatives. The production and uses of the compound of the present invention have been generally described above, and the production will be specifically explained with examples along with listing elemental analysis values, infrared absorption spectra, NMR spectra, and physical properties. <Example 1> 134 g (1.0 mol) of 4-methylacetophenone was added dropwise to 530 g (5.3 mol) of 98% sulfuric acid while maintaining the temperature at 15°C, and the mixture was stirred at the same temperature for 30 minutes. Next, sulfuric anhydride 560°C was added while cooling to 5-10°C.
g (7.0 mol) was added dropwise, and stirring was continued for 5 hours while maintaining the temperature at 5°C. The obtained reaction solution was diluted by adding it to Water 2, and then 2187 g (24.6 mol) of a 45% aqueous sodium hydroxide solution was added to neutralize it. After the neutralized reaction solution was heated to 60°C, it was slowly cooled to 34°C, and the produced sodium 5-acetyl-2-methylsulfonate was crystallized and collected. The yield is 228.5g and the purity is 95%.
It was 92.0%. Thereafter, reactions were carried out in the same manner as in Example 1 using the amounts shown in Table 1, and the results shown in Table 1 were obtained.
【表】
取得品をエタノールで抽出・精製した５―アセ
チル―２―メチルベンゼンスルホン酸ナトリウム
の分析値および物性は次の通りであつた。
(1) 元素分析％（C9H9O4SNaとして）
（MW＝236）
計算値 Ｃ：45.8 Ｈ：3.8 Ｓ：13.6 Na：9.7
実測値 Ｃ：45.6 Ｈ：3.9 Ｓ：13.7 Na：9.6
(2) 赤外吸収スペクトル νＫＢｒ ｎａｘcm-1
3500，2950，1670，1595，
1550，1420，1380，1350，
1290，1245，1190，1095，
1065，1020，950，830，
800，720，700，675，
620，580，550，480，
(3) NMRスペクトル
δ：8.35〜8.15（1H，singlet）
7.90〜7.60（1H，doublet）
7.40〜7.10（1H，doublet）
2.60〜2.55（3H，singlet）
2.40〜2.55（3H，singlet）
(4) 水、低級アルコールに可溶、他有機溶媒には
ほとんど溶解しない。[Table] The analytical values and physical properties of sodium 5-acetyl-2-methylbenzenesulfonate, which was extracted and purified with ethanol, were as follows. (1) Elemental analysis% (as C 9 H 9 O 4 SNa)
(MW=236) Calculated value C: 45.8 H: 3.8 S: 13.6 Na: 9.7 Actual value C: 45.6 H: 3.9 S: 13.7 Na: 9.6 (2) Infrared absorption spectrum ν KBr nax cm -1 3500, 2950, 1670，1595，1550，1420，1380，1350，1290，1245，1190，1095，1065，1020，950，830，800，720，700，675，620，580，550，480，(3) NMRspectrumδ :8.35~8.15 (1H, singlet) 7.90~7.60 (1H, doublet) 7.40~7.10 (1H, doublet) 2.60~2.55 (3H, singlet) 2.40~2.55 (3H, singlet) (4) Applicable to water and lower alcohols It is hardly soluble in other organic solvents.
Claims (1)
水硫酸もしくは発煙硫酸と反応させてスルホン化
することを特徴とする５―アセチル―２―アルキ
ルベンゼンスルホン酸またはその塩の製造法。 ２ スルホン化反応を20℃以下０℃以上の温度で
行なう特許請求の範囲１記載の方法。 ３ ４―アルキルアセトフエノン１モルに対し濃
硫酸を３〜15モル、無水硫酸または発煙硫酸中の
SO3の量を２〜15モルそれぞれ添加し反応させる
特許請求の範囲１記載の方法。 ４ アルキル基がメチル基である特許請求の範囲
１記載の方法。 ５ アルカリ金属がナトリウムまたはカリウムで
ある特許請求の範囲１記載の方法。[Claims] 1. A method for producing 5-acetyl-2-alkylbenzenesulfonic acid or a salt thereof, which comprises reacting 4-alkylacetophenone with sulfuric anhydride or fuming sulfuric acid in concentrated sulfuric acid to sulfonate it. . 2. The method according to claim 1, wherein the sulfonation reaction is carried out at a temperature of 20°C or lower and 0°C or higher. 3 For 1 mole of 4-alkylacetophenone, add 3 to 15 moles of concentrated sulfuric acid, anhydrous sulfuric acid or oleum.
The method according to claim 1, wherein the reaction is carried out by adding SO 3 in an amount of 2 to 15 moles. 4. The method according to claim 1, wherein the alkyl group is a methyl group. 5. The method according to claim 1, wherein the alkali metal is sodium or potassium.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9097682A JPS58206550A (en) | 1982-05-27 | 1982-05-27 | 5-acetyl-2-alkylbenzenesulfonic acid, its salt and their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9097682A JPS58206550A (en) | 1982-05-27 | 1982-05-27 | 5-acetyl-2-alkylbenzenesulfonic acid, its salt and their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58206550A JPS58206550A (en) | 1983-12-01 |
| JPS6140661B2 true JPS6140661B2 (en) | 1986-09-10 |
Family
ID=14013541
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9097682A Granted JPS58206550A (en) | 1982-05-27 | 1982-05-27 | 5-acetyl-2-alkylbenzenesulfonic acid, its salt and their preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58206550A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0162404B1 (en) * | 1984-05-15 | 1988-08-24 | Seitetsu Kagaku Co., Ltd. | Process for preparing 2-alkyl-5-haloacetylbenzenesulfonamide |
| JPS61229859A (en) * | 1985-04-03 | 1986-10-14 | Seitetsu Kagaku Co Ltd | 5-acetyl-2-alkylbenzenesulfonic acid-n,n-dialkylaniline salt and production thereof |
| JPS60239457A (en) * | 1984-05-15 | 1985-11-28 | Seitetsu Kagaku Co Ltd | Preparation of 5-acetyl-2-alkylbenzenesulfonyl chloride |
| JPS60239459A (en) * | 1984-05-15 | 1985-11-28 | Seitetsu Kagaku Co Ltd | Preparation of 5-acetyl-2-alkylbenzenesulfonamide |
-
1982
- 1982-05-27 JP JP9097682A patent/JPS58206550A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58206550A (en) | 1983-12-01 |
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