CN111718286A - Industrial production method of aromatic hydrocarbon sulfonyl chloride with power supply group - Google Patents
Industrial production method of aromatic hydrocarbon sulfonyl chloride with power supply group Download PDFInfo
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- CN111718286A CN111718286A CN202010714926.2A CN202010714926A CN111718286A CN 111718286 A CN111718286 A CN 111718286A CN 202010714926 A CN202010714926 A CN 202010714926A CN 111718286 A CN111718286 A CN 111718286A
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- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
- C07C303/08—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with halogenosulfonic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
- C07C303/06—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
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Abstract
The invention provides an industrial production method of arene sulfonyl chloride with an electron supply group, which comprises the following steps: (1) and (3) sulfonation reaction: premixing with a solvent, preheating (cold) treated liquid sulfur trioxide, adding a positioning agent, and carrying out a homogeneous continuous sulfonation reaction with aromatic hydrocarbon with an electric supply group in the presence of the solvent; (2) acyl chlorination reaction: premixing with a solvent, preheating (cold) treated chlorosulfonic acid, adding a catalyst, and carrying out homogeneous continuous acylation chlorination reaction on a product generated by the sulfonation reaction in the step (1); generating aromatic hydrocarbon sulfonyl chloride with power supply groups, hydrolyzing excessive chlorosulfonic acid, separating acid and desolventizing to generate aromatic hydrocarbon sulfonic acid chloride with power supply groups. The production process of the invention has no hydrogen chloride gas generated in the whole reaction process, can realize pipeline continuous reaction, has stable production and easy control, and has less amount of dangerous chemicals stored in a system with the same production scale and good intrinsic safety.
Description
Technical Field
The invention relates to an industrial production method of arene sulfonyl chloride with an electric supply group, in particular to a novel process for continuously or intermittently producing arene sulfonyl chloride with an electric supply group by using liquid sulfur trioxide and chlorosulfonic acid in a solvent.
Background
The arene sulfonyl chloride with the power supply group generated by sulfonating and acyl-chlorinating arene with the power supply group is an important fine chemical product, is an important intermediate for the industries of medicine, dye, pigment and plastic additive, and has very wide application.
At present, there are several methods for industrially producing sulfonic acid chloride of aromatic hydrocarbon with a power supply group, but most of them are produced by reacting aromatic hydrocarbon with a power supply group with excessive chlorosulfonic acid and then hydrolyzing the excessive chlorosulfonic acid, but different additives such as phosphorus oxychloride, inorganic ammonium salt, alkali metal or alkaline earth metal, etc. are added during sulfonation reaction in consideration of the amount of isomers, and there are some changes in reaction temperature and hydrolysis manner, etc. in the related art, see german patents DE1172258, DE1112978, US patent US3686300, japanese patent JP 56-46860, chinese patents CN1824649, CN1405151, CN1049213, CN1436773A, etc.
In the traditional process flow, as shown in a figure l, aromatic hydrocarbon with an electric supply group is adopted to directly react with excessive chlorosulfonic acid, so that a large amount of waste sulfuric acid and waste hydrochloric acid are generated, the treatment is difficult, and the three wastes are polluted greatly; and the separation of the later stage material and the waste acid is not easy: meanwhile, the use of a large amount of chlorosulfonic acid causes the synthesis cost to be overhigh and the production lacks competitiveness; in the large-scale production process, the safety of the production apparatus is very poor due to the use of a large amount of chlorosulfonic acid in the batch reaction system.
Disclosure of Invention
The invention aims to provide an industrial production process of arene sulfonyl chloride with an electric supply group, so as to reduce the pollution to the environment, improve the safety of a production device and reduce the production cost.
The technical scheme of the invention is as follows:
an industrial production method of arene sulfonyl chloride with an electron supply group comprises the following steps:
(1) and (3) sulfonation reaction: preheating (cooling) liquid sulfur trioxide premixed with a solvent to the temperature of a reaction system (-20-200 ℃), adding a positioning agent, and carrying out a homogeneous continuous sulfonation reaction on aromatic hydrocarbon with a power supply group in the solvent;
the reaction vessel is a continuous dynamic multiphase plug flow reaction system formed by combining a dynamic mixer and a pipeline reactor continuous sulfonation reactor, or a continuous dynamic multiphase plug flow reaction system formed by combining a static mixer and a pipeline reactor continuous sulfonation reactor, or a kettle type intermittent sulfonation reactor.
(2) Acyl chlorination reaction: preheating (cooling) chlorosulfonic acid premixed with a solvent to the temperature of a reaction system (-20-200 ℃), adding a catalyst, and carrying out homogeneous continuous acyl chlorination reaction on a product generated by the sulfonation reaction in the step (1); generating aromatic hydrocarbon sulfonyl chloride with the power supply group, hydrolyzing slightly excessive chlorosulfonic acid, separating acid and desolventizing to generate aromatic hydrocarbon sulfonic acid chloride with the power supply group.
The reaction vessel is a continuous dynamic multiphase plug flow reaction system formed by combining a dynamic mixer and a pipeline reactor continuous acyl chlorination reactor, or a continuous dynamic multiphase plug flow reaction system formed by combining a static mixer and a pipeline reactor continuous acyl chlorination reaction, or a kettle type intermittent acyl chlorination reaction.
Wherein the substituent on the benzene ring of the aromatic hydrocarbon with the power supply group comprises the following components:
strong electron-donating group: dialkylamino, alkylamino, amino, hydroxy, alkoxy;
medium electron donating groups: amide groups, acyloxy groups;
weakly electron donating groups: alkyl, carboxymethyl, phenyl.
The solvent used in the sulfonation reaction in the step (1) and the acyl chlorination reaction in the step (2) comprises: liquid arene sulfonyl chloride semi-finished product with an electric supply group, DMF, DMC, EMC, DEC, PC, DME, ethyl acetate, 1, 4-dioxane, acetonitrile, phosphorus trichloride, thionyl chloride, silicon tetrachloride, oxalyl chloride, isocyanate, phosphorus oxychloride, thionyl chloride, sulfonyl chloride, disulfide dichloride, sulfur tetrachloride, chlorine, diphosgene, dimethyldichlorosilane, methyltrichlorosilane, trimethylchlorosilane, methyldichlorosilane, monoethyltrichlorosilane, diethyldichlorosilane, triethylchlorosilane, ethyldichlorosilane, diethylchlorosilane and the like or a mixed solvent of a plurality of the solvents which is formed according to a certain proportion, or the mixed solvent composed of the above single-component solvent and halogenated hydrocarbon of C1-C4 according to a certain proportion, wherein the mass ratio of the single-component solvent to the halogenated hydrocarbon of C1-C4 is as follows: 0.5 to 99.5 percent.
Under the reaction condition, when the semi-finished product of the arene sulfonyl chloride with the power supply group is in a liquid state, the semi-finished product is preferably a reaction system solvent; as the liquid semi-finished product is used as a reaction system solvent, the occurrence of side reactions such as ortho (particularly meta) sulfonic acid/sulfonyl chloride and the like can be inhibited, and the yield and the selectivity of the product can be further improved.
Under the reaction conditions, when the semi-finished product of the arene sulfonyl chloride with the power supply group is not in a liquid state, the solvent is preferably: and (3) when phosphorus trichloride, thionyl chloride, silicon tetrachloride, oxalyl chloride, isocyanate, phosphorus oxychloride, thionyl chloride, sulfuryl chloride, disulfide dichloride, sulfur tetrachloride, chlorine and diphosgene are used as a solvent system, the presence of the solvent can promote the proceeding of acyl chlorination, and the reaction in the step (2) is catalyzed.
The molar ratio of the liquid sulfur trioxide to the aromatic hydrocarbon with the power supply group in the step (1) is 1-2: 1; the molar ratio of the aromatic hydrocarbon with the power supply group to the chlorosulfonic acid in the step (2) is 1: 1-2.
The positioning agent in the step (1) is one or a mixture of N-fluoro-diphenyl sulfonamide, acetic acid, ammonium acetate, ammonium sulfate and xylene sulfone according to a certain proportion.
In the step (2), the catalyst is one or a mixture of several of DMF, triethylamine, pyridine, dimethylaminopyridine, DMAC, 4-dimethylaminopyridine and triethylene diamine according to a certain proportion.
The addition of the catalyst greatly promotes the reaction of acyl chlorination.
In the step (1), a continuous dynamic multiphase plug flow reaction system formed by combining liquid sulfur trioxide and a reactor with power supply group aromatic hydrocarbon, preferably a dynamic mixer and a pipeline reactor is selected; the efficiency of the continuous sulfonation reaction carried out by using the reaction equipment is much higher than that of one or the combination of two of a static mixer, a batch kettle reactor and a pipeline reactor, the reaction time is shorter and the unit efficiency is higher.
In the step (2), a reactor of chlorosulfonic acid and aromatic sulfonic acid with a power supply group, preferably a continuous dynamic multiphase plug flow reaction system formed by combining a dynamic mixer and a pipeline reactor, is adopted; the continuous acyl chlorination reaction carried out by utilizing the reaction equipment has higher reaction efficiency than one or the combination of two of a static mixer, a batch kettle reactor and a pipeline reactor, shorter reaction time and higher unit efficiency.
Through the pipeline continuous production, the dangerous chemical substances of the production system can be greatly reduced, the intrinsic safety of the system is realized, the investment of the device is reduced, and the economic benefit is improved.
Before the reaction in the step (1), premixing liquid sulfur trioxide and a solvent according to a certain mass ratio (0.5-99.5%), and heating (or cooling) to a proper temperature (-20-200 ℃); this is favorable to mass transfer and heat transfer of sulfonation reaction, can raise sulfonation yield and position sulfonic acid group, and is favorable to selectivity of product.
Before the reaction in the step (2), the chlorosulfonic acid and the solvent are premixed according to a certain mass ratio (0.5-99.5%) and heated (or cooled) to a proper temperature (-20-200 ℃); the method is favorable for mass transfer and heat transfer of the acyl chlorination reaction, can improve the acyl chlorination yield and position sulfonyl chloride groups, and is favorable for the selectivity of products.
Before the reaction in the step (1), premixing liquid sulfur trioxide and a solvent according to a certain mass ratio (0.5-99.5%), and heating (or cooling) to a proper temperature (-20-200 ℃); adding a positioning agent, and then carrying out sulfonation reaction with the aromatic hydrocarbon with the power supply group in a solvent system, wherein the selectivity of the product can be greatly improved under the action of the positioning agent.
By replacing part of chlorosulfonic acid with liquid sulfur trioxide, the method not only can greatly reduce the production cost, but also can greatly reduce the emission of waste acid and waste gas, thereby achieving the purpose of emission reduction.
The solvent participates in the reaction to ensure that the whole process is liquefied, thereby not only providing possibility for the continuous reaction process of a continuous dynamic multiphase plug flow reaction system (or a static mixer and a pipeline reactor) formed by combining a dynamic mixer and the pipeline reactor, but also directly realizing the direct separation of waste acid.
Meanwhile, the preparation method can realize the byproduct of the aromatic hydrocarbon sulfonic acid with the power supply group, and greatly improves the operation efficiency of the device.
The invention has the beneficial effects that:
the invention uses liquid-phase sulfur trioxide as a sulfonating agent instead, which is the most economic synthesis mode in organic synthesis, does not produce any pollution, only connects sulfur trioxide to a benzene ring, is a green clean synthesis process, and has qualitative leap over the traditional sulfonation by using sulfuric acid and chlorosulfonic acid. The aromatic sulfonic acid with the power supply group of the sulfonated product further reacts with chlorosulfonic acid without generating hydrogen chloride gas and waste hydrochloric acid, and the byproduct sulfuric acid is greatly reduced compared with the traditional process, thereby having obvious clean production characteristics. Meanwhile, the energy consumption is greatly reduced due to the adoption of the pipelining reaction. The sulfur trioxide has relatively small molecular weight and the price is less than half of that of chlorosulfonic acid, so that the sulfur trioxide is used for substituting chlorosulfonic acid for sulfonation, thereby greatly reducing the production cost. In addition, the use of the solvent in the new process greatly reduces the activity of the liquid sulfur trioxide, makes direct sulfonation possible and improves the yield. Meanwhile, the solvent variety and the ratio of the solvent variety to the reactant are adjusted, so that partial positioning effect can be directly realized.
The production process of the invention has no hydrogen chloride gas generated in the whole reaction process, can realize pipeline continuous reaction, has stable production and easy control, and has less amount of dangerous chemicals stored in a system with the same production scale and good intrinsic safety. The method avoids the defects of poor intrinsic safety and high energy consumption caused by the adoption of intermittent reaction, difficulty in production control, more unorganized hydrogen chloride emission, and large amount of dangerous chemicals stored in a system with the same production scale in the traditional process.
Drawings
FIG. 1 is a flow diagram of a conventional process for the production of arenesulfonyl chlorides with an electron donating group.
FIG. 2 is a flow chart of a production process of the arene sulfonyl chloride with the power supply group.
Detailed Description
The present invention is further illustrated by the following examples, which are not intended to limit the scope of the invention.
The process flow of the invention for producing the aromatic hydrocarbon sulfonyl chloride with the power supply group is shown in figure 2, and the reaction formula is as follows:
aromatic hydrocarbon + SO 3/solvent with power supply group
Aromatic hydrocarbon/solvent with power supply group
Aromatic hydrocarbon/solvent + HSO3Cl with electron donating group
Aromatic hydrocarbon sulfonyl chloride + sulfuric acid with power supply group
Example 1
Toluene (diethyldichlorosilane) solution with the flow rate of 92kg/h and the concentration of 20% is cooled by a metering pump, precooled liquid sulfur trioxide (diethyldichlorosilane) solution with the flow rate of 84kg/h and the concentration of 20% is added into ammonium acetate serving as a positioning agent, then the cooled solution and the ammonium acetate are simultaneously injected into a dynamic mixer, the mixture is fully mixed by the dynamic mixer and then is sent into a pipeline reactor for continuous sulfonation, and the temperature is controlled to be 50-60 ℃ for reaction.
The reacted feed liquid and precooled chlorosulfonic acid (containing 50% of solvent and 500ppm of catalyst DMF) with the flow rate of 24kg/h enter a static mixer together, the mixture is sent into a chlorination pipeline reactor after being mixed, the reaction temperature is controlled to be 60-70 ℃, the reaction is finished and enters a continuous desolventizing system, the solvent is removed, then the product enters a crystallizing system, 38.4kg/h of benzene sulfonyl chloride is separated, the product purity is 98%, and the yield is 98.3%.
Example 2
Adding 810kg of acetanilide and 500kg of chloroform + silicon tetrachloride mixed solvent (3 kg of positioning agent xylene sulfone) into a 3000L reaction kettle with a stirrer, a thermometer and a charging opening, starting stirring, dripping 1250kg of liquid sulfur trioxide/(chloroform + silicon tetrachloride mixture) solution (the concentration of sulfur trioxide is 40%) at the temperature of 10-20 ℃, keeping the temperature for 1 hour after dripping, adding 1400kg of chlorosulfonic acid (containing 500kg of solvent and 5kg of catalyst) at the temperature of 50 +/-2 ℃, and keeping the temperature for 1 hour after dripping to 70-80 ℃.
Standing for 8h, cooling to 20 deg.C, adding appropriate amount of water to decompose excessive chlorosulfonic acid, cooling to no more than 28 deg.C, demixing, removing solvent layer, filtering, and washing filter cake to pH 3-4 to obtain p-acetamidobenzenesulfonyl chloride 1317kg with purity of 96% and yield of 90.2%.
Example 3
Adding 20 g of DMF (dimethyl formamide) into a 500ml four-neck flask with a stirrer, a thermometer and a charging hole, starting stirring, then simultaneously dropwise adding 0.1mol of phenol and 0.105mol of liquid sulfur trioxide (containing 20 g of DMF), controlling the temperature to be minus 20-0 ℃ for reaction, after dropwise adding, keeping the temperature for 2 hours, then adding 0.13mol of chlorosulfonic acid at minus 20 ℃, after dropwise adding, keeping the temperature for 2 hours at 60-70 ℃.
Cooling to 20 ℃, adding a small amount of water for washing, layering, and desolventizing a solvent layer to obtain 18 g of p-hydroxybenzene sulfonyl chloride product with the purity of 93.5 percent and the yield of 87.5 percent.
Example 4
0.1mol of benzene (containing 10 g of 1, 4-dioxane) is added into a 500ml four-neck flask with a stirrer, a thermometer and a charging hole, stirring is started, 0.12mol of liquid sulfur trioxide (containing 80 g of 1, 4-dioxane) is dripped at the temperature of 60-80 ℃, the temperature is kept for l hours after dripping, then 0.116mol of chlorosulfonic acid is added at the temperature of 60-70 ℃, and the temperature is kept for 1 hour after dripping and heating to-20-0 ℃.
Cooling to 20 deg.c, washing with small amount of water, layering, and desolventizing to obtain 17.3 g of methyl benzenesulfonyl chloride product with purity of 95.3% and yield of 93.5%.
Claims (9)
1. An industrial production method of arene sulfonyl chloride with an electron donating group is characterized by comprising the following steps:
(1) and (3) sulfonation reaction: premixing with a solvent, adding a positioning agent into liquid sulfur trioxide subjected to waste heat or precooling treatment, and carrying out homogeneous continuous sulfonation reaction with aromatic hydrocarbon with an electric supply group in the presence of the solvent;
(2) acyl chlorination reaction: premixing with a solvent, adding a catalyst into the mixture, and performing homogeneous continuous acylation chlorination reaction on the mixture and a product generated by sulfonation reaction in the step (1) by using waste heat or precooled chlorosulfonic acid; generating aromatic hydrocarbon sulfonyl chloride with power supply groups, hydrolyzing excessive chlorosulfonic acid, separating acid and desolventizing to generate aromatic hydrocarbon sulfonic acid chloride with power supply groups.
2. The industrial production method of an aromatic hydrocarbon sulfonyl chloride with an electric supply group as claimed in claim 1, wherein the substituent on the benzene ring of the aromatic hydrocarbon with the electric supply group is any one of the following:
strong electron-donating group: dialkylamino, alkylamino, amino, hydroxy, alkoxy;
medium electron donating groups: amide groups, acyloxy groups;
weakly electron donating groups: alkyl, carboxymethyl, phenyl.
3. The method for industrially producing an aromatic hydrocarbon sulfonyl chloride with an electron donating group according to claim 1, wherein the solvent used in the step (1) and the step (2) comprises: liquid arene sulfonyl chloride semi-finished products with power supply groups, DMF, DMC, EMC, DEC, PC, DME, ethyl acetate, 1, 4-dioxane, acetonitrile, phosphorus trichloride, thionyl chloride, silicon tetrachloride, oxalyl chloride, isocyanate, phosphorus oxychloride, thionyl chloride, sulfonyl chloride, disulfide dichloride, sulfur tetrachloride, chlorine, diphosgene, dimethyldichlorosilane, methyltrichlorosilane, trimethylchlorosilane, methyldichlorosilane, monoethyltrichlorosilane, diethyldichlorosilane, triethylchlorosilane, ethyldichlorosilane and diethylchlorosilane, or a mixed solvent of a plurality of the solvents according to a certain proportion;
or the mixed solvent of the above single-component solvent and halogenated hydrocarbon of C1-C4, wherein the mass ratio of the single-component solvent to the halogenated hydrocarbon of C1-C4 is as follows: 0.5 to 99.5 percent.
4. The industrial production method of arene sulfonyl chloride with an electric supply group as claimed in claim 1, wherein the positioning agent in the step (1) is one or a mixture of N-fluoro-diphenyl sulfonamide, acetic acid, ammonium acetate, ammonium sulfate and xylene sulfone; the molar ratio of the liquid sulfur trioxide to the aromatic hydrocarbon with the power supply group in the step (1) is 1-2: 1.
5. The industrial production method of arene sulfonyl chloride with an electron donating group according to claim 1, wherein the catalyst in the step (2) is one or a mixture of several of DMF, triethylamine, pyridine, dimethylaminopyridine, DMAC, 4-dimethylaminopyridine and triethylene diamine; the molar ratio of the aromatic hydrocarbon sulfonation product with the power supply group to chlorosulfonic acid in the step (2) is 1: 1-2.
6. The industrial production method of aromatic hydrocarbon sulfonyl chloride with an electric supply group as claimed in claim 1, wherein the reaction vessels in the steps (1) and (2) are a continuous dynamic multiphase plug flow reaction system formed by combining a dynamic mixer and a pipeline reactor, a continuous dynamic multiphase plug flow reaction system formed by combining a static mixer and a pipeline reactor, or a kettle type batch reaction system.
7. The industrial production method of aromatic hydrocarbon sulfonyl chloride with an electric supply group as claimed in claim 1, wherein the main reactant liquid sulfur trioxide or chlorosulfonic acid of the step (1) and the step (2) is premixed with a solvent by a mass ratio of 0.5-99.5% and reacted at a temperature of-20-200 ℃.
8. The industrial production method of arenesulfonyl chloride with electron donating group as claimed in claim 1, wherein when the arenesulfonyl chloride with electron donating group is liquid under the corresponding reaction conditions, the arenesulfonyl chloride with electron donating group is used as the solvent in step (1) and step (2).
9. The industrial production method of arene sulfonyl chloride with an electric supply group as claimed in claim 1, wherein when the semi-finished arene sulfonyl chloride with an electric supply group is not in a liquid state under the corresponding reaction conditions, phosphorus trichloride, thionyl chloride, silicon tetrachloride, oxalyl chloride, isocyanate, phosphorus oxychloride, sulfuryl chloride, sulfonyl chloride, disulfide dichloride, sulfur tetrachloride, chlorine and diphosgene are used as the solvent system in the step (1) and the step (2).
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113277965A (en) * | 2021-05-21 | 2021-08-20 | 金华双宏化工有限公司 | Method for continuously synthesizing paratoluensulfonyl chloride by using microchannel reactor |
| CN113582883A (en) * | 2021-08-03 | 2021-11-02 | 金华双宏化工有限公司 | Method for continuously synthesizing p-toluenesulfonyl chloride |
| CN113800486A (en) * | 2021-09-14 | 2021-12-17 | 山东凯盛新材料股份有限公司 | Production process of bis (chlorosulfonyl) imide |
| CN115710204A (en) * | 2022-11-21 | 2023-02-24 | 金华双宏化工有限公司 | Method for continuously synthesizing benzene sulfonyl chloride |
| CN116253667A (en) * | 2022-12-27 | 2023-06-13 | 煤炭科学研究总院有限公司 | Aggregation-induced emission material and preparation method thereof |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1922136A (en) * | 2004-02-25 | 2007-02-28 | 惠氏公司 | Processes for the preparation of aryl-and heteroaryl-alkylsulfonyl halides |
| CN101195593A (en) * | 2007-07-31 | 2008-06-11 | 浙江嘉化集团股份有限公司 | Industrial production method of alkylbenzene sulfonyl chloride |
| CN103304451A (en) * | 2013-05-13 | 2013-09-18 | 台州市前进化工有限公司 | Preparation method of aromatic hydrocarbon sulfonyl chloride derivative |
| CN103508880A (en) * | 2013-10-09 | 2014-01-15 | 江西吉翔医药化工有限公司 | Method for synthesizing 3,5-dichlorobenzoyl chloride |
| CN105111111A (en) * | 2015-09-10 | 2015-12-02 | 泰兴市臻庆化工有限公司 | Preparation method for aryl sulfonyl chloride derivative |
| CN106866466A (en) * | 2017-02-16 | 2017-06-20 | 吴赣药业（苏州）有限公司 | A kind of method for synthesizing N-acetylsulfanilyl chloride as sulfonating agent with sulfur trioxide |
| CN108640860A (en) * | 2018-06-12 | 2018-10-12 | 新乡市锦源化工有限公司 | The preparation method and N-acetylsulfanilyl chloride of the N-acetylsulfanilyl chloride of green energy conservation |
| CN109232327A (en) * | 2018-10-31 | 2019-01-18 | 浙江工业大学上虞研究院有限公司 | A kind of method that toluene sulfonation prepares p-methyl benzenesulfonic acid |
-
2020
- 2020-07-23 CN CN202010714926.2A patent/CN111718286A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1922136A (en) * | 2004-02-25 | 2007-02-28 | 惠氏公司 | Processes for the preparation of aryl-and heteroaryl-alkylsulfonyl halides |
| CN101195593A (en) * | 2007-07-31 | 2008-06-11 | 浙江嘉化集团股份有限公司 | Industrial production method of alkylbenzene sulfonyl chloride |
| CN103304451A (en) * | 2013-05-13 | 2013-09-18 | 台州市前进化工有限公司 | Preparation method of aromatic hydrocarbon sulfonyl chloride derivative |
| CN103508880A (en) * | 2013-10-09 | 2014-01-15 | 江西吉翔医药化工有限公司 | Method for synthesizing 3,5-dichlorobenzoyl chloride |
| CN105111111A (en) * | 2015-09-10 | 2015-12-02 | 泰兴市臻庆化工有限公司 | Preparation method for aryl sulfonyl chloride derivative |
| CN106866466A (en) * | 2017-02-16 | 2017-06-20 | 吴赣药业（苏州）有限公司 | A kind of method for synthesizing N-acetylsulfanilyl chloride as sulfonating agent with sulfur trioxide |
| CN108640860A (en) * | 2018-06-12 | 2018-10-12 | 新乡市锦源化工有限公司 | The preparation method and N-acetylsulfanilyl chloride of the N-acetylsulfanilyl chloride of green energy conservation |
| CN109232327A (en) * | 2018-10-31 | 2019-01-18 | 浙江工业大学上虞研究院有限公司 | A kind of method that toluene sulfonation prepares p-methyl benzenesulfonic acid |
Non-Patent Citations (2)
| Title |
|---|
| KATHRINC ESARZ等: "Gaschromatographic Analysis of Aromatic Sulphonic Acids.The Sulphonation of Aromatic Hydrocarbons and Related Compounds", 《JOURNAL FUER PRAKTISCHE CHEMIE (LEIPZIG)》 * |
| 安德列-斯坦科维茨等: "《化工装置的再设计 过程强化》", 30 September 2012 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113277965A (en) * | 2021-05-21 | 2021-08-20 | 金华双宏化工有限公司 | Method for continuously synthesizing paratoluensulfonyl chloride by using microchannel reactor |
| CN113582883A (en) * | 2021-08-03 | 2021-11-02 | 金华双宏化工有限公司 | Method for continuously synthesizing p-toluenesulfonyl chloride |
| CN113582883B (en) * | 2021-08-03 | 2022-11-04 | 金华双宏化工有限公司 | Method for continuously synthesizing p-toluenesulfonyl chloride |
| WO2023010649A1 (en) * | 2021-08-03 | 2023-02-09 | 金华双宏化工有限公司 | Method for continuous synthesis of p-toluenesulfonyl chloride |
| CN113800486A (en) * | 2021-09-14 | 2021-12-17 | 山东凯盛新材料股份有限公司 | Production process of bis (chlorosulfonyl) imide |
| CN115710204A (en) * | 2022-11-21 | 2023-02-24 | 金华双宏化工有限公司 | Method for continuously synthesizing benzene sulfonyl chloride |
| CN115710204B (en) * | 2022-11-21 | 2024-01-09 | 金华双宏化工有限公司 | Method for continuously synthesizing benzenesulfonyl chloride |
| CN116253667A (en) * | 2022-12-27 | 2023-06-13 | 煤炭科学研究总院有限公司 | Aggregation-induced emission material and preparation method thereof |
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