CN116947707A - Continuous preparation method, device and system for acetamido benzenesulfonyl chloride - Google Patents

Continuous preparation method, device and system for acetamido benzenesulfonyl chloride Download PDF

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Publication number
CN116947707A
CN116947707A CN202211309117.9A CN202211309117A CN116947707A CN 116947707 A CN116947707 A CN 116947707A CN 202211309117 A CN202211309117 A CN 202211309117A CN 116947707 A CN116947707 A CN 116947707A
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China
Prior art keywords
reaction
acetanilide
chlorosulfonic acid
chloride
liquid
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CN202211309117.9A
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Inventor
孙宝昌
刘士豪
邹海魁
肖光辉
初广文
牛圣操
陈建峰
刘利明
罗勇
米建彬
付纪文
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Shijiazhuang Hehe Chemical Fertilizer Co ltd
Beijing University of Chemical Technology
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Shijiazhuang Hehe Chemical Fertilizer Co ltd
Beijing University of Chemical Technology
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Priority to CN202211309117.9A priority Critical patent/CN116947707A/en
Publication of CN116947707A publication Critical patent/CN116947707A/en
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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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J14/00—Chemical processes in general for reacting liquids with liquids; Apparatus specially adapted therefor
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/0006—Controlling or regulating processes
    • B01J19/0013—Controlling the temperature of the process
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/18—Stationary reactors having moving elements inside
    • B01J19/1862—Stationary reactors having moving elements inside placed in series
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J4/00—Feed or outlet devices; Feed or outlet control devices
    • B01J4/001—Feed or outlet devices as such, e.g. feeding tubes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J4/00—Feed or outlet devices; Feed or outlet control devices
    • B01J4/02—Feed or outlet devices; Feed or outlet control devices for feeding measured, i.e. prescribed quantities of reagents
    • 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
    • C07C303/08—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

Abstract

The application discloses a continuous preparation method of acetaminophen sulfonyl chloride, which takes liquid acetanilide and chlorosulfonic acid as raw materials, continuously inputs the liquid acetanilide and chlorosulfonic acid into a hypergravity reactor for reaction, then introduces the liquid acetanilide and chlorosulfonic acid into a stirred tank for secondary reaction, and carries out chlorination treatment on the reaction product to obtain the acetaminophen sulfonyl chloride. According to the application, the supergravity device is adopted as the sulfonation reactor, the generation of local hot spots in the reaction process is avoided through the reinforced mixing and mass transfer of materials, the product yield is high, the pressure sensing is arranged in the supergravity reactor, the continuous sulfonation process is realized, the whole process automatic linkage control can be realized, the process parameters are accurately regulated and controlled, the reaction device is obviously reduced, the demand and the labor intensity of workers are greatly reduced, the production process is safer, and the production cost is lower.

Description

Continuous preparation method, device and system for acetamido benzenesulfonyl chloride
Technical Field
The application relates to the technical field of synthesis of dye and medical intermediates, in particular to a continuous preparation method, device and system of acetamido benzenesulfonyl chloride.
Background
The acetamido benzene sulfonyl chloride is an important intermediate in the industries of dye and medicine manufacture, and has wide application in the fields of paint, plastics, pesticides and the like.
The industrial production of the acetamido benzene sulfonyl chloride mainly comprises two production processes of direct chlorosulfonation of chlorosulfonic acid and chlorination of acetamido benzene sulfonic acid. The chlorosulfonic acid direct chlorosulfonation method refers to that chlorosulfonic acid and acetanilide are subjected to sulfonation reaction and chlorination reaction in sequence to prepare the acetamido benzenesulfonyl chloride. The chlorination method of acetamido benzene sulfonic acid is to use chlorosulfonic acid or sulfur trioxide to carry out sulfonation reaction, and then to carry out chlorination reaction by taking thionyl chloride, phosphorus pentachloride, oxalyl chloride, phosphorus oxychloride and the like as chlorinating agents to obtain the acetamido benzene sulfonyl chloride.
The patent and literature report about the synthesis process of acetamido benzene sulfonyl chloride at home and abroad, for example, the patent literature of publication No. CN1683331A discloses a production process of acetamido benzene sulfonyl chloride, which is prepared by taking solid acetanilide as a raw material and chlorosulfonating the solid acetanilide, hydrogen chloride generated by chlorosulfonic acid decomposition is circularly absorbed to prepare hydrochloric acid, and 40-50% of dilute sulfuric acid serving as a byproduct is used for recycling the acetamido benzene sulfonic acid. The application comprehensively utilizes byproducts in the production process, saves water, reduces production cost and protects environment. However, the process uses acetanilide solid as raw material, the conversion rate is only about 80%, the raw material utilization rate is too low, the production efficiency is low, and the product quality is unstable. Patent document CN113563234a discloses a synthesis process for producing p-aminobenzenesulfonyl chloride by an organic solvent method, wherein p-acetamido benzenesulfonyl chloride is produced by using chloroform or the like as a solvent, chlorosulfonic acid as a sulfonating agent, and thionyl chloride as a chlorinating agent. However, the use of organic solvents may cause problems such as pollution of waste organic solvents.
At present, batch method is mostly adopted for sulfonation in the production process of acetamido benzene sulfonyl chloride at home and abroad.
Firstly, chlorosulfonic acid is added into a reaction kettle, then acetanilide solid is slowly added, as sulfonation reaction is a strong exothermic process, the reaction temperature is controlled by indirectly transferring heat in a jacket reaction kettle in the reaction process, the feeding time is usually more than 6-8 hours, the heat preservation reaction is also required to be carried out for 2 hours after the feeding is completed, then thionyl chloride is dropwise added for chlorination reaction, and the mixture is added into ice water for dilution and hydrolysis after the reaction is completed. This process has the following disadvantages: 1. the liquid acetanilide obtained in the acetanilide production section is required to be cooled and sliced, then is added into a sulfonation reactor in a solid state to react with chlorosulfonic acid, and reacts with chlorosulfonic acid while the acetanilide is dissolved, so that the reaction rate is low and the production efficiency is low; 2. because the stirred tank reactor has huge volume and poor mass transfer and mixing efficiency, the partial reaction temperature is easily caused to be too high, thereby causing the excessive standard of byproducts, and the generated gas is not easy to be discharged, so that the product yield and the production efficiency are reduced; 3, due to the adoption of intermittent operation, the requirement of workers is large, the labor intensity is high, and the quality stability of products is poor; 4. at present, frozen brine or circulating water is used as an external refrigerant for the domestic sulfonation reaction to directly cool the reaction kettle, and the risk of severe reaction explosion of chlorosulfonic acid, sulfonation leakage and cooling water exists.
Disclosure of Invention
The application provides a preparation process of acetamido benzene sulfonyl chloride, which takes liquid acetanilide and chlorosulfonic acid as raw materials, takes a supergravity reactor as a sulfonation reactor, controls the reaction temperature through material circulation, has high raw material conversion rate, high production efficiency, less manual demand, obviously improves the product quality stability and realizes the intrinsic safety of the process.
In order to solve at least one of the above problems, the present application provides, in a first aspect, a continuous production method of acetaminophen sulfonyl chloride, comprising:
leading liquid acetanilide and chlorosulfonic acid reactant into a hypergravity reactor to obtain reaction materials, wherein the leading-in port of the hypergravity reactor comprises a sealing wall, a pressure sensor is arranged on the sealing wall, and the sealing wall is opened when the pressure sensor bears pressure so as to realize continuous automatic opening;
introducing the reaction materials into a stirring kettle for secondary reaction to obtain secondary reaction materials;
carrying out chlorination reaction on part of the secondary reaction material and thionyl chloride to obtain the acetamido benzenesulfonyl chloride;
and introducing the rest of the secondary reaction material into the hypergravity reactor.
Preferably, the continuous preparation method of the acetamido benzene sulfonyl chloride further comprises the following steps:
and adopting a heat exchanger to cool the rest secondary reaction materials.
Preferably, the mass ratio of chlorosulfonic acid to acetanilide is 1.75-3.5.
Preferably, the feed mass ratio of the remaining part of the secondary reaction material to the acetanilide is 50-200:1.
In a second aspect, the present application provides a continuous production apparatus for acetaminophen sulfonyl chloride, comprising: a gravity assembly, a secondary reaction assembly and a chlorination assembly;
the liquid outlet of the hypergravity component is connected with the liquid inlet of the secondary reaction component, liquid acetanilide and chlorosulfonic acid reactant which are led into the liquid outlet of the hypergravity component can be mixed and sheared to obtain reaction materials, the inlet of the hypergravity component comprises a sealing wall, a pressure sensor is arranged on the sealing wall, and the sealing wall is opened when the pressure sensor bears pressure so as to realize continuous automatic opening;
the secondary reaction assembly comprises two liquid outlets, wherein one liquid outlet is connected with the chlorination assembly, and can be used for carrying out secondary mixing on part of the reaction materials to obtain secondary reaction materials;
and the chlorination component performs chlorination reaction on part of the secondary reaction materials to obtain the acetamido benzenesulfonyl chloride.
Preferably, the continuous preparation device of acetamido benzenesulfonyl chloride further comprises: and the other liquid outlet of the secondary reaction component is connected with the circulating component, and the circulating component can circulate the rest secondary reaction material into the chlorosulfonic acid reactant.
Preferably, the continuous preparation device of acetamido benzenesulfonyl chloride further comprises: the heat exchange assembly can cool the chlorosulfonic acid reactant and the rest of the secondary reaction materials.
Preferably, the hypergravity assembly comprises: the cutting filler is used for shearing and mixing the liquid acetanilide and the chlorosulfonic acid reactant.
In a third aspect, the present application provides a continuous preparation system for acetaminophen sulfonyl chloride, comprising: an acetamido benzenesulfonyl chloride preparation device, a chlorosulfonic acid feed line and a liquid acetanilide feed line as described above.
The beneficial effects of the application are that
1. The raw material acetanilide in the supergravity reactor is directly conveyed in a liquid state, so that the feeding rate of the acetanilide can be accurately controlled, the reaction of the acetanilide and chlorosulfonic acid is liquid-liquid reaction, the reaction efficiency is high, the raw material acetanilide is directly conveyed from an acetanilide production section, the process of cooling and slicing the acetanilide in the original solid feeding process and then conveying the acetanilide in a solid form is omitted, the production process is simplified, and the process is more energy-saving and environment-friendly;
2. according to the application, the supergravity reactor is used as the sulfonation reactor, the high-speed rotation filler greatly strengthens the mixing and mass transfer process between the acetanilide, the chlorosulfonic acid and the circulating materials, eliminates local hot spots, accelerates the reaction rate, and remarkably improves the product quality stability.
3. According to the application, the pressure sensor is arranged in the supergravity reactor, so that the continuous sulfonation process is realized, the whole process can be automatically controlled in a linkage manner, the technological parameters can be accurately regulated and controlled, the reaction device is obviously reduced, the demand and the labor intensity of workers are greatly reduced, the production process is safer, and the production cost is lower.
Drawings
In order to more clearly illustrate the embodiments of the application or the technical solutions in the prior art, the drawings which are used in the description of the embodiments or the prior art will be briefly described, it being obvious that the drawings in the description below are only some embodiments of the application, and that other drawings can be obtained from them without inventive effort for a person skilled in the art.
FIG. 1 is a schematic diagram of a device for preparing acetaminophen sulfonyl chloride in an embodiment of the present application;
Detailed Description
The following description of the embodiments of the present application will be made clearly and fully with reference to the accompanying drawings, in which it is evident that the embodiments described are only some, but not all embodiments of the application. All other embodiments, which can be made by those skilled in the art based on the embodiments of the present application without making any inventive effort, are intended to fall within the scope of the present application.
For convenience of description, the description of "first", "second", etc. in this application is provided for descriptive purposes only and is not to be construed as indicating or implying a relative importance or the number of technical features indicated. Thus, a feature defining "a first" or "a second" may explicitly or implicitly include at least one such feature. In addition, the technical solutions of the embodiments may be combined with each other, but it is necessary to base that the technical solutions can be realized by those skilled in the art, and when the technical solutions are contradictory or cannot be realized, the combination of the technical solutions should be considered to be absent and not within the scope of protection claimed in the present application.
Based on the problems that the prior art obtains liquid acetanilide through cooling and slicing, then the liquid acetanilide is added into a sulfonation reactor in a solid state to react with chlorosulfonic acid, the acetanilide is dissolved and reacts with chlorosulfonic acid, the reaction rate is low and the production efficiency is low, the application provides a continuous preparation method of acetaminophen sulfonyl chloride, which comprises the following steps:
leading liquid acetanilide and chlorosulfonic acid reactant into a hypergravity reactor to obtain reaction materials, wherein the leading-in port of the hypergravity reactor comprises a sealing wall, a pressure sensor is arranged on the sealing wall, and the sealing wall is opened when the pressure sensor bears pressure so as to realize continuous automatic opening;
introducing the reaction materials into a stirring kettle for secondary reaction to obtain secondary reaction materials;
carrying out chlorination reaction on part of the secondary reaction material and thionyl chloride to obtain the acetamido benzenesulfonyl chloride;
and introducing the rest of the secondary reaction material into the hypergravity reactor.
In the embodiment, chlorosulfonic acid reactant is mixed with acetanilide liquid in a hypergravity reactor after being metered and reacts, a pressure sensor at the inlet of the hypergravity reactor is automatically started after bearing pressure, the reacted material enters a stirring kettle through a liquid outlet of the hypergravity reactor, and the material leaving the stirring kettle is subjected to chlorination treatment to obtain the product acetaminophenesulfonyl chloride.
In order to improve the utilization rate of raw materials, in the embodiment, a part of reaction materials leaving the stirring kettle are circulated as circulating materials and are mixed with chlorosulfonic acid after being cooled by a heat exchanger, on one hand, the temperature of the system can be controlled, the circulating reaction materials can be used as a heat transfer carrier, in addition, the utilization rate of chlorosulfonic acid can be improved, the consumption of chlorosulfonic acid is reduced, and the other part of materials are extracted to enter a chlorination reactor to be subjected to chlorination reaction with thionyl chloride, so that a p-acetamido benzenesulfonyl chloride product is obtained. The high gravity sulfonation reactor, the stirring kettle and the heat exchanger form a reaction circulation system, the high gravity reactor is discharged to the stirring kettle and then circulated back to the high gravity reactor through a pump for continuous reaction, and the sulfonation product is extracted to enter the chlorination reactor for chlorination reaction after reaching a certain liquid level in the stirring kettle.
The specific type of heat exchanger is not limited in the present application, and the oil cooler is preferred as it is well known to those skilled in the art; in the application, by using the oil cooler, cold brine or circulating water is firstly used for cooling the external refrigerant (oil), cooled cold oil is cooled with the sulfonation reaction material, the risk of chlorosulfonic acid leakage and cooling water reaction explosion is solved from the source, and the safety performance is improved.
In summary, according to the continuous preparation method of the acetaminophen sulfonyl chloride, the reaction raw material acetanilide is directly conveyed in a liquid state, so that the feeding rate of the acetanilide can be accurately controlled, the reaction of the acetanilide and chlorosulfonic acid is liquid-liquid reaction, the reaction efficiency is high, the raw material acetanilide is directly conveyed by a pump from an acetanilide production section, the process of cooling and slicing the acetanilide in the original solid feeding process is omitted, and then the acetanilide is conveyed in a solid form, so that the production process is simplified, and the process is more energy-saving and environment-friendly; according to the application, the supergravity reactor is adopted as the sulfonation reactor, the mixing and mass transfer process among the acetanilide, chlorosulfonic acid and circulating materials is greatly enhanced by the filler rotating at high speed, so that not only is the local hot spot eliminated and the reaction rate accelerated, but also the reaction temperature is accurately regulated and controlled by the circulating heat transfer of the materials, and the product quality stability is remarkably improved; meanwhile, the continuous sulfonation process is realized, the whole process can be automatically controlled in a linkage manner, the process parameters are accurately regulated and controlled, the reaction device is obviously reduced, the demand and the labor intensity of workers are greatly reduced, the production process is safer, and the production cost is lower. According to the application, the oil cooler is used as a heat exchanger, cold brine or circulating water is used for cooling an external refrigerant (oil), cooled cold oil is cooled with the sulfonation reaction material, the risk of chlorosulfonic acid leakage and cooling water reaction explosion is solved from the source, and the safety performance is improved.
In some other embodiments, the feed mass ratio of chlorosulfonic acid to acetanilide is 1.75 to 3.5:1, preferably 2 to 3:1; the molar ratio of chlorosulfonic acid to acetanilide in the sulfonation reaction process is 2-4, preferably 2.5-3.3; the feed mass ratio of the circulating material to the liquid acetanilide is 40:200:1, preferably 60-150:1. If the feed ratio is too low, the reaction of the acetanilide is incomplete, the viscosity of the material is high, and the material is easy to be locally overheated; if the feed ratio is too high, the amount of acid-containing waste water generated in the hydrolysis process is large.
Preferably, the temperature of the circulating reaction system is controlled by automatic interlocking with an external refrigerant, and the reaction temperature is 30-55 ℃, preferably 45-50 ℃. If the temperature is too low, the reactivity is reduced, the reaction time is long, and the production efficiency is low; if the temperature is too high, the reaction rate is too high, byproducts are increased, and potential safety hazards exist.
In the application, the average residence time of the reaction materials chlorosulfonic acid and liquid acetanilide in a reaction system formed by the hypergravity reactor and the stirring kettle is 0-60min, preferably 1-20min, and more preferably 5-15min.
In the application, the sulfonation reaction process adopts material external circulation heat removal to control the reaction temperature, and the specific operation process comprises the following steps: the liquid acetanilide and chlorosulfonic acid enter a hypergravity sulfonation reactor in proportion to react, the sulfonated product flows into a stirring kettle, the discharge of reactants is controlled by a DCS automatic system, and the sulfonated product enters the chlorination reactor.
The application provides a device for realizing the preparation method of the acetamido benzenesulfonyl chloride, which is shown in figure 1 and comprises the following steps: a hypergravity component, a secondary reaction component and a chlorination component;
the liquid outlet of the hypergravity component is connected with the liquid inlet of the secondary reaction component, liquid acetanilide and chlorosulfonic acid reactant which are led into the liquid outlet of the hypergravity component can be mixed and sheared to obtain reaction materials, the inlet of the hypergravity component comprises a sealing wall, a pressure sensor is arranged on the sealing wall, and the sealing wall is opened when the pressure sensor bears pressure so as to realize continuous automatic opening;
the secondary reaction assembly comprises two liquid outlets, wherein one liquid outlet is connected with the chlorination assembly, and can be used for carrying out secondary mixing on part of the reaction materials to obtain secondary reaction materials;
and the chlorination component performs chlorination reaction on part of the secondary reaction materials to obtain the acetamido benzenesulfonyl chloride.
In this embodiment, after the pressure sensor at the inlet of the hypergravity assembly receives pressure, the hypergravity assembly is automatically opened, chlorosulfonic acid reactant and acetanilide liquid are introduced, after the chlorosulfonic acid reactant and the acetanilide liquid are mixed and react in the hypergravity assembly, the reaction material enters the secondary reaction assembly, the reaction material is extracted from the secondary reaction assembly and enters the chlorination assembly to carry out chlorination reaction with thionyl chloride, and the acetamido benzenesulfonyl chloride product is obtained, and the secondary reaction assembly can be a stirred tank.
In some other embodiments, the acetaminophen sulfonyl chloride continuous production apparatus further comprises: and the other liquid outlet of the secondary reaction component is connected with the circulating component, and the circulating component can circulate the rest secondary reaction material into the chlorosulfonic acid reactant.
In order to further improve the utilization rate of reactants, a part of secondary reaction materials obtained in the secondary reaction component is chlorinated to obtain a p-acetamido benzenesulfonyl chloride product, and the other part of the secondary reaction materials is circulated into the hypergravity component through the circulation component, wherein the circulation component can be a circulation pump, and the circulation materials are introduced into the circulation pump and pumped into the hypergravity component through the circulation pump.
In some other embodiments, the acetaminophen sulfonyl chloride continuous production apparatus further comprises: the heat exchange assembly can cool the chlorosulfonic acid reactant and the rest of the secondary reaction materials.
In this embodiment, after the part of the reaction materials involved in the circulation is cooled by the heat exchange component, the utilization rate of the reactants can be improved, and the reaction materials can also be used as a heat transfer carrier, so that the temperature of the whole reaction system can be controlled.
In some other embodiments, the supergravity assembly comprises: the cutting filler is used for shearing and mixing the liquid acetanilide and the chlorosulfonic acid reactant.
The specific type of the hypergravity reactor is not limited in the application, and the application is well known to the person skilled in the art, such as a rotary packed bed, a baffling type, a spiral channel type, a rotary disc type, a fixed rotor type and other hypergravity rotating devices disclosed in the prior art.
The rotary packed bed comprises a shell and a rotor, wherein the rotor is internally provided with a filler, the rotor is driven by a motor, and the filler rotating at high speed tears liquid into very fine or very small liquid drops, liquid films or liquid filaments, so that the mixing and mass transfer among materials are greatly enhanced.
In summary, according to the continuous preparation device for acetaminophen sulfonyl chloride, provided by the application, the reaction raw material acetanilide is directly conveyed in a liquid state, so that the feeding rate of the acetanilide can be accurately controlled, the reaction between the acetanilide and chlorosulfonic acid is liquid-liquid reaction, the reaction efficiency is high, the raw material acetanilide is directly conveyed by a pump from an acetanilide production section, the process of cooling and slicing the acetanilide in the original solid feeding process is eliminated, and then the acetanilide is conveyed in a solid form, so that the production process is simplified, and the process is more energy-saving and environment-friendly; according to the application, the supergravity reactor is adopted as the sulfonation reactor, the mixing and mass transfer process among the acetanilide, chlorosulfonic acid and circulating materials is greatly enhanced by the filler rotating at high speed, so that not only is the local hot spot eliminated and the reaction rate accelerated, but also the reaction temperature is accurately regulated and controlled by the circulating heat transfer of the materials, and the product quality stability is remarkably improved; meanwhile, the continuous sulfonation process is realized, the whole process can be automatically controlled in a linkage manner, the process parameters are accurately regulated and controlled, the reaction device is obviously reduced, the demand and the labor intensity of workers are greatly reduced, the production process is safer, and the production cost is lower. According to the application, the oil cooler is used as a heat exchanger, cold brine or circulating water is used for cooling an external refrigerant (oil), cooled cold oil is cooled with the sulfonation reaction material, the risk of chlorosulfonic acid leakage and cooling water reaction explosion is solved from the source, and the safety performance is improved.
The application also provides an acetamido benzenesulfonyl chloride preparation system, which comprises: a continuous preparation device of acetamido benzene sulfonyl chloride, a chlorosulfonic acid feeding pipeline and a liquid acetanilide feeding pipeline. The chlorosulfonic acid from the chlorosulfonic acid storage tank is mixed with circulating materials cooled by the heat exchange assembly and enters the supergravity assembly after being metered by the pump and the flowmeter, the acetanilide liquid from the acetanilide production section enters the supergravity assembly after being metered by the flowmeter, the two materials are contacted and mixed in the supergravity assembly and react, the reacted materials enter the secondary reaction assembly through the liquid outlet of the supergravity assembly, a part of the materials leaving the secondary reaction assembly circulate and are mixed with chlorosulfonic acid after being cooled by the heat exchange assembly, and the other part of the materials are extracted and enter the chlorination assembly to carry out chlorination reaction with thionyl chloride, so that the acetamido benzenesulfonyl chloride is obtained. The application is not limited to the type of secondary reaction module, and a stirred tank is preferred.
In summary, the continuous preparation method, the device and the system for the acetaminophen sulfonyl chloride provided by the application have the advantages that the raw material acetanilide in the supergravity reactor is directly conveyed in a liquid state, the feeding rate of the acetanilide can be accurately controlled, the reaction between the acetanilide and chlorosulfonic acid is a liquid-liquid reaction, the reaction efficiency is high, the raw material acetanilide is directly conveyed by a pump from an acetanilide production section, the process of cooling and slicing the acetanilide in the original solid feeding process is eliminated, and then the process is more energy-saving and environment-friendly; the high-gravity reactor is adopted as the sulfonation reactor, the mixing and mass transfer process among the acetanilide, the chlorosulfonic acid and the circulating materials is greatly enhanced by the filler rotating at high speed, so that not only is the local hot spot eliminated and the reaction rate accelerated, but also the reaction temperature is accurately regulated and controlled by the circulating heat transfer of the materials, and the product quality stability is remarkably improved; the continuous sulfonation process is realized by adopting the supergravity reactor, the whole process can be automatically controlled in a linkage way, the technological parameters are accurately regulated and controlled, the reaction device is obviously reduced, the demand and the labor intensity of workers are greatly reduced, the production process is safer, and the production cost is lower. After the oil cooler is used, cold brine or circulating water is used for cooling an external refrigerant (oil), cooled cold oil is cooled with a sulfonation reaction material, the risk of chlorosulfonic acid leakage and cooling water reaction explosion is solved from the source, and the safety performance is improved.
The continuous production system of acetaminophen sulfonyl chloride provided by the present application will be described with reference to specific examples.
Example 1:
in the embodiment, the feeding flow of liquid acetanilide is 15kg/h, the feeding flow of chlorosulfonic acid is 45, two materials continuously enter a hypergravity reactor, the discharged materials of the hypergravity reactor flow into a stirring kettle, the temperature of the whole reaction circulation system is controlled at 50 ℃, the flow of circulating materials is 1800kg/h, the rotating speed of the hypergravity reactor is 600rpm, the average residence time of the reaction materials in the reaction circulation system is 5min, the materials leaving the stirring kettle enter a chlorination reactor and react with thionyl chloride to obtain the acetaminophen sulfonyl chloride, and the product is analyzed, wherein the product yield is 92%.
Example 2:
in the embodiment, the feeding flow of liquid acetanilide is 15kg/h, the feeding flow of chlorosulfonic acid is 36kg/h, two materials continuously enter a hypergravity reactor, the discharged materials of the hypergravity reactor flow into a stirring kettle, the temperature of the whole reaction circulation system is controlled at 45 ℃, the flow of circulating materials is 1500kg/h, the rotating speed of the hypergravity reactor is 1000rpm, the average residence time of the reaction materials in the reaction circulation system is 15min, the materials leaving the stirring kettle enter a chlorination reactor and react with thionyl chloride to obtain the acetaminophenesulfonyl chloride, the product is analyzed, and the product yield is 91.6%.
Example 3:
in the embodiment, the feeding flow of liquid acetanilide is 15kg/h, the feeding flow of chlorosulfonic acid is 50kg/h, two materials continuously enter a hypergravity reactor, the discharged materials of the hypergravity reactor flow into a stirring kettle, the temperature of the whole reaction circulation system is controlled at 35 ℃, the flow of circulating materials is 1200kg/h, the rotating speed of the hypergravity reactor is 1200rpm, the average residence time of the reaction materials in the reaction circulation system is 30min, the materials leaving the stirring kettle enter a chlorination reactor and react with thionyl chloride to obtain the acetaminophenesulfonyl chloride, the product is analyzed, and the product yield is 90.8%.
In the description of the present specification, a description referring to terms "one embodiment," "some embodiments," "examples," "specific examples," or "some examples," etc., means that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the present specification. In this specification, schematic representations of the above terms are not necessarily directed to the same embodiment or example.
Furthermore, the various embodiments or examples described in this specification and the features of the various embodiments or examples may be combined and combined by those skilled in the art without contradiction. The above description is merely an embodiment of the present specification and is not intended to limit the present specification. Various modifications and changes may be made to the embodiments herein by those skilled in the art. Any modification, equivalent replacement, improvement, or the like, which is made within the spirit and principle of the embodiments of the present specification, should be included in the scope of the claims of the embodiments of the present specification.

Claims (9)

1. A continuous preparation method of acetamido benzene sulfonyl chloride is characterized by comprising the following steps:
leading liquid acetanilide and chlorosulfonic acid reactant into a hypergravity reactor to obtain reaction materials, wherein the leading-in port of the hypergravity reactor comprises a sealing wall, a pressure sensor is arranged on the sealing wall, and the sealing wall is opened when the pressure sensor bears pressure so as to realize continuous automatic opening;
introducing the reaction materials into a stirring kettle for secondary reaction to obtain secondary reaction materials;
carrying out chlorination reaction on part of the secondary reaction material and thionyl chloride to obtain the acetamido benzenesulfonyl chloride;
and introducing the rest of the secondary reaction material into the hypergravity reactor.
2. The continuous production method of acetaminophen sulfonyl chloride according to claim 1, further comprising:
and adopting a heat exchanger to cool the rest secondary reaction materials.
3. The continuous preparation method of acetaminophen sulfonyl chloride according to claim 2, wherein the mass ratio of chlorosulfonic acid to acetanilide is 1.75-3.5:1.
4. The continuous production method of acetaminophen chloride as claimed in claim 2, wherein the feeding mass ratio of the remaining secondary reaction material to acetanilide is 50-200:1.
5. A continuous preparation device for acetamido benzenesulfonyl chloride, which is characterized by comprising: a hypergravity component, a secondary reaction component and a chlorination component;
the liquid outlet of the hypergravity component is connected with the liquid inlet of the secondary reaction component, liquid acetanilide and chlorosulfonic acid reactant which are led into the liquid outlet of the hypergravity component can be mixed and sheared to obtain reaction materials, the inlet of the hypergravity component comprises a sealing wall, a pressure sensor is arranged on the sealing wall, and the sealing wall is opened when the pressure sensor bears pressure so as to realize continuous automatic opening;
the secondary reaction assembly comprises two liquid outlets, wherein one liquid outlet is connected with the chlorination assembly, and can be used for carrying out secondary mixing on part of the reaction materials to obtain secondary reaction materials;
and the chlorination component performs chlorination reaction on part of the secondary reaction materials to obtain the acetamido benzenesulfonyl chloride.
6. The apparatus for continuously producing acetaminophen chloride as claimed in claim 5, wherein the apparatus for continuously producing acetaminophen chloride further comprises: and the other liquid outlet of the secondary reaction component is connected with the circulating component, and the circulating component can circulate the rest secondary reaction material into the chlorosulfonic acid reactant.
7. The apparatus for continuously producing acetaminophen chloride as claimed in claim 5, wherein the apparatus for continuously producing acetaminophen chloride further comprises: the heat exchange assembly can cool the chlorosulfonic acid reactant and the rest of the secondary reaction materials.
8. The continuous production apparatus of acetaminophen chloride as claimed in claim 5, wherein said supergravity assembly comprises: the cutting filler is used for shearing and mixing the liquid acetanilide and the chlorosulfonic acid reactant.
9. A continuous preparation system for acetamido benzenesulfonyl chloride, which is characterized by comprising: a continuous production apparatus for acetaminophen chloride, as claimed in claims 5 to 8, a chlorosulfonic acid feed line and a liquid acetanilide feed line.
CN202211309117.9A 2022-10-25 2022-10-25 Continuous preparation method, device and system for acetamido benzenesulfonyl chloride Pending CN116947707A (en)

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