JPH0244304B2 - - Google Patents
Info
- Publication number
- JPH0244304B2 JPH0244304B2 JP57093360A JP9336082A JPH0244304B2 JP H0244304 B2 JPH0244304 B2 JP H0244304B2 JP 57093360 A JP57093360 A JP 57093360A JP 9336082 A JP9336082 A JP 9336082A JP H0244304 B2 JPH0244304 B2 JP H0244304B2
- Authority
- JP
- Japan
- Prior art keywords
- bromobenzenesulfonyl chloride
- bromobenzene
- chlorosulfuric acid
- reaction
- chloride
- 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 - Lifetime
Links
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims description 22
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 13
- VFPWGZNNRSQPBT-UHFFFAOYSA-N 2-bromobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1Br VFPWGZNNRSQPBT-UHFFFAOYSA-N 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 8
- 150000008282 halocarbons Chemical class 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 1
- 239000011734 sodium Substances 0.000 claims 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- KMMHZIBWCXYAAH-UHFFFAOYSA-N 4-bromobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(Br)C=C1 KMMHZIBWCXYAAH-UHFFFAOYSA-N 0.000 description 5
- 229910052936 alkali metal sulfate Inorganic materials 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical class C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 2
- JPOXNPPZZKNXOV-UHFFFAOYSA-N bromochloromethane Chemical compound ClCBr JPOXNPPZZKNXOV-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 125000004436 sodium atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、高純度なブロモベンゼンスルホニル
クロリドの製造に関するものである。
（従来の技術）
従来、ハロゲンベンゼンスルホニルクロリドを
製造する方法としては、種々の方法が知られてい
るが、工業的な製法としては、ハロゲンベンゼン
をクロロ硫酸と反応する方法が知られている。そ
の際に、副反応をおさえる方法として、クロロホ
ルム、四塩化炭素などの溶媒を用いる方法（日本
科学会編「新実験化学講座（第14巻）有機化合物
の合成と反応（）丸善（昭53.2.20、p.1787〜
1788）等がある。
（発明が解決しようとする問題点）
しかしながら、これらの方法は反応条件を選ぶ
ことによつても、２〜10％のジフエニルスルホン
類の副生をさけることはできないので、高純度な
ハロゲンベンゼンスルホニルクロリドを得るため
には、精製をしなければならないという欠点を有
していた。
（問題を解決するための手段）
本発明者らは、簡単な操作で、ジフエニルスル
ホン類等の副生をおさえ、高純度、高収率でブロ
モベンゼンスルホニルクロリドを製造する方法に
ついて鋭意研究を重ねた結果、ハロゲン化炭化水
素溶媒中、ブロモベンゼンとクロロ硫酸を反応さ
せる際、アルカリ金属の硫酸塩を添加すれば、従
来の問題点が解決しうることを見出し、この知見
に基づいて本発明をなすに至つた。
すなわち本発明は、ハロゲン化炭化水素溶媒
中、ブロモベンゼンとクロロ硫酸とを反応させた
ブロモベンゼンスルホニルクロリドを製造する方
法において、一般式
Y2SO4 (1)
（式中、Ｙはナトリウム原子またはカリウム原子
を表す。）で示されるアルカリ金属の硫酸塩を添
加することを特徴とするブロモベンゼンスルホニ
ルクロリドの製造法である。
本発明のおいて添加物として使用する前記一般
式(1)で示されるアルカリ金属の硫酸塩としては、
例えば硫酸ナトリウム、硫酸カリウムをあげるこ
とができる。
また、反応溶媒として使用するハロゲン化炭化
水素としては、例えば四塩化炭素、クロロホル
ム、１，２−ジクロロエタン、１，１，２，２−
テトラクロロエチレン、クロロブロモメタン等を
あげることができる。
本発明におけるクロロ硫酸の使用量は、ブロモ
ベンゼン１モルに対して２モル以上、好ましくは
2.5〜５モルであり、またアルカリ金属の硫酸塩
の添加量としては、ブロモベンゼン１モルに対し
て0.1〜１モル、好ましくは0.2〜0.33モルである。
ハロゲン化炭化水素溶媒の使用量は反応混合物が
充分に撹拌できる量であれつばよく、ブロモベン
ゼン１モルに対し150ｇ以上あれば充分である。
ブロモベンゼンとクロロ硫酸との反応方法は、
ハロゲン化炭化水素溶媒と共にクロロ硫酸および
アルカリ金属の硫酸塩を仕込んでおき、これに加
熱撹拌下ブロモベンゼンを滴下反応させる方法が
よく、反応温度は20〜100℃、好ましくは40〜80
℃が適当である。反応時間は、反応温度または溶
媒などの種類により選定すればよいが、40〜80℃
では１〜５時間あれば充分である。
反応によつて得られる反応混合物は、水を滴下
し過剰のクロロ硫酸を分解した後分液、水洗し、
次いで反応溶媒を留去する方法等の常法に従つて
後処理することにより目的とする高純度のブロモ
ベンゼンスルホニルクロリドを得ることができ
る。
本発明の方法の特徴は、ハロゲン化炭化水素溶
媒中、ブロモベンゼンとクロロ硫酸を反応させる
際、アルカリ金属の硫酸塩を添加することによ
り、添加しない場合に比較しジフエニルスルホン
類を1/5〜1/15に抑え精製をしないで高純度のブ
ロモベンゼンスルホニルクロリドを製造できるこ
とであり、従来の方法に比べ簡単な操作でしかも
経済的に製造できる等格別の効果を奏するもので
あり高純度のブロモベンゼンスルホニルクロリド
の工業的製造方法として効果の高い方法である。
次に本発明の方法を実施例および比較例により
具体的に説明する。
実施例 １
温度計、コンデンサーおよび撹拌機を備えた２
四つ口反応フラスコに四塩化炭素670ml、98％
クロロ硫酸349.6ｇ（3.00モル）および硫酸ナト
リウム46.9（0.33モル）を仕込み、撹拌下40℃に
加熱した。これにブロモベンゼン157.0ｇ（1.00
モル）を２時間かけて滴下してさらに70℃で２時
間加熱撹拌をつづけ、その後10℃に冷却し、水
670mlを20℃以下に保ちながら滴下して過剰のク
ロロ硫酸を分解し、次いで水500mlで洗浄し、四
塩化炭素を留去して、４−ブロモベンゼンスルホ
ニリクロリド253.2ｇ（収率99.1％）を得た。こ
のものをガスクロマトグラフイーにより分析した
結果、４−ブロモベンゼンスルホニルクロリド
98.9％、２−ブロモベンゼンスルホニルクロリド
0.6％、4.4′−ジブロモジフエニルスルホン0.2％
であつた。
４−ブロモフエニルスルホニルクロリドの純収
率は98.0％であつた。
比較例 １
実施例１の硫酸ナトリウムを入れないで、実施
例１と同様に反応させ４−ブロモベンゼンスルホ
ニルクロリド239.0ｇ（収率93.5％）を得た。こ
のものをガスクロマトグラフイーにより分析した
結果、４−ブロモベンゼンスルホニルクロリド
96.5％、２−ブロモベンゼンスルホニルクロリド
1.0％、4.4′−ジブロモジフエニルスルホン2.3％
であつた。
４−ブロモフエニルスルホニルクロリドの純収
率は90.2％であつた。
実施例 ２〜６
実施例１と同様な方法でブロモベンゼン、クロ
ロ硫酸、硫酸ナトリウム、四塩化炭素の種類また
は使用量を変え反応を行なつた。得られた結果を
次表に示す。
【表】DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to the production of highly pure bromobenzenesulfonyl chloride. (Prior Art) Conventionally, various methods have been known for producing halogenbenzenesulfonyl chloride, and a method of reacting halogenbenzene with chlorosulfuric acid is known as an industrial production method. At that time, a method of suppressing side reactions is to use solvents such as chloroform and carbon tetrachloride (edited by the Japanese Science Society, "New Experimental Chemistry Course (Volume 14), Synthesis and Reactions of Organic Compounds"), Maruzen (February 1982). 20, p.1787~
1788) etc. (Problems to be Solved by the Invention) However, these methods cannot avoid the by-product of 2 to 10% diphenyl sulfones even by selecting reaction conditions. It has the disadvantage that purification is required to obtain sulfonyl chloride. (Means for Solving the Problem) The present inventors have conducted extensive research on a method for producing bromobenzenesulfonyl chloride with high purity and high yield through simple operations while suppressing by-products such as diphenylsulfones. As a result of repeated experiments, it was discovered that the conventional problems could be solved by adding an alkali metal sulfate when reacting bromobenzene and chlorosulfuric acid in a halogenated hydrocarbon solvent.Based on this knowledge, the present invention was developed. I was able to accomplish this. That is, the present invention provides a method for producing bromobenzenesulfonyl chloride by reacting bromobenzene and chlorosulfuric acid in a halogenated hydrocarbon solvent, which has the general formula Y 2 SO 4 (1) (wherein, Y is a sodium atom or This is a method for producing bromobenzenesulfonyl chloride, which is characterized by adding a sulfate of an alkali metal represented by (representing a potassium atom). The alkali metal sulfate represented by the general formula (1) used as an additive in the present invention includes:
Examples include sodium sulfate and potassium sulfate. Examples of halogenated hydrocarbons used as reaction solvents include carbon tetrachloride, chloroform, 1,2-dichloroethane, 1,1,2,2-
Examples include tetrachloroethylene and chlorobromomethane. The amount of chlorosulfuric acid used in the present invention is 2 mol or more per 1 mol of bromobenzene, preferably
The amount of the alkali metal sulfate added is 0.1 to 1 mol, preferably 0.2 to 0.33 mol, per mol of bromobenzene.
The amount of halogenated hydrocarbon solvent to be used is sufficient as long as the reaction mixture can be stirred sufficiently, and 150 g or more per mole of bromobenzene is sufficient. The reaction method between bromobenzene and chlorosulfuric acid is
A good method is to charge chlorosulfuric acid and an alkali metal sulfate together with a halogenated hydrocarbon solvent, and then dropwise react bromobenzene therewith with heating and stirring.The reaction temperature is 20 to 100°C, preferably 40 to 80°C.
°C is appropriate. The reaction time can be selected depending on the reaction temperature or type of solvent, but it is 40 to 80℃.
1 to 5 hours is sufficient. The reaction mixture obtained by the reaction is separated by adding water dropwise to decompose excess chlorosulfuric acid, and then washed with water.
The desired high purity bromobenzenesulfonyl chloride can then be obtained by post-treatment according to a conventional method such as distilling off the reaction solvent. The feature of the method of the present invention is that when bromobenzene and chlorosulfuric acid are reacted in a halogenated hydrocarbon solvent, by adding an alkali metal sulfate, diphenyl sulfones are reduced to 1/5 compared to the case without addition. It is possible to produce high-purity bromobenzenesulfonyl chloride with a reduction of ~1/15 and no purification, and it is an exceptionally effective method that can be produced easily and economically compared to conventional methods. This is a highly effective method for industrially producing bromobenzenesulfonyl chloride. Next, the method of the present invention will be specifically explained using Examples and Comparative Examples. Example 1 2 equipped with thermometer, condenser and stirrer
670 ml of carbon tetrachloride, 98% in a four-necked reaction flask.
349.6 g (3.00 moles) of chlorosulfuric acid and 46.9 g (0.33 moles) of sodium sulfate were charged and heated to 40° C. with stirring. To this, bromobenzene 157.0g (1.00
mol) was added dropwise over 2 hours, continued heating and stirring at 70°C for 2 hours, then cooled to 10°C, and added water.
Excess chlorosulfuric acid was decomposed by adding 670 ml dropwise while keeping the temperature below 20°C, followed by washing with 500 ml of water and distilling off carbon tetrachloride to obtain 253.2 g of 4-bromobenzenesulfonylichloride (yield 99.1%). I got it. Analysis of this product by gas chromatography revealed that it was 4-bromobenzenesulfonyl chloride.
98.9%, 2-bromobenzenesulfonyl chloride
0.6%, 4.4'-dibromodiphenyl sulfone 0.2%
It was hot. The pure yield of 4-bromophenylsulfonyl chloride was 98.0%. Comparative Example 1 239.0 g (yield: 93.5%) of 4-bromobenzenesulfonyl chloride was obtained by carrying out a reaction in the same manner as in Example 1 without adding the sodium sulfate used in Example 1. Analysis of this product by gas chromatography revealed that it was 4-bromobenzenesulfonyl chloride.
96.5%, 2-bromobenzenesulfonyl chloride
1.0%, 4.4′-dibromodiphenyl sulfone 2.3%
It was hot. The pure yield of 4-bromophenylsulfonyl chloride was 90.2%. Examples 2 to 6 Reactions were carried out in the same manner as in Example 1 by changing the types or amounts of bromobenzene, chlorosulfuric acid, sodium sulfate, and carbon tetrachloride. The results obtained are shown in the table below. 【table】
Claims (1)
とクロロ硫酸とを反応させたブロモベンゼンスル
ホニルクロリドを製造する方法において、一般式 Y2SO4 (1) （式中、Ｙはナトリウム原子またはカリウム原子
を表す。）で示されるアルカリ金属の硫酸塩を添
加することを特徴とするブロモベンゼンスルホニ
ルクロリドの製造法。[Scope of Claims] 1. A method for producing bromobenzenesulfonyl chloride by reacting bromobenzene and chlorosulfuric acid in a halogenated hydrocarbon solvent, with the general formula Y 2 SO 4 (1) (wherein, Y is sodium A method for producing bromobenzenesulfonyl chloride, which comprises adding a sulfate of an alkali metal represented by (representing an atom or a potassium atom).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57093360A JPS58210058A (en) | 1982-06-01 | 1982-06-01 | Preparation of high purity halogenobenzenesulfonyl chloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57093360A JPS58210058A (en) | 1982-06-01 | 1982-06-01 | Preparation of high purity halogenobenzenesulfonyl chloride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58210058A JPS58210058A (en) | 1983-12-07 |
| JPH0244304B2 true JPH0244304B2 (en) | 1990-10-03 |
Family
ID=14080111
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57093360A Granted JPS58210058A (en) | 1982-06-01 | 1982-06-01 | Preparation of high purity halogenobenzenesulfonyl chloride |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58210058A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5838253A (en) * | 1981-08-31 | 1983-03-05 | Mitsui Toatsu Chem Inc | Preparation of 4-chlorobenzenesulfonyl chloride |
-
1982
- 1982-06-01 JP JP57093360A patent/JPS58210058A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5838253A (en) * | 1981-08-31 | 1983-03-05 | Mitsui Toatsu Chem Inc | Preparation of 4-chlorobenzenesulfonyl chloride |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58210058A (en) | 1983-12-07 |
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