WO2022099692A1 - Method and system for synthesizing 2-chloro-5-trifluoromethyl pyridine - Google Patents

Method and system for synthesizing 2-chloro-5-trifluoromethyl pyridine Download PDF

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WO2022099692A1
WO2022099692A1 PCT/CN2020/129058 CN2020129058W WO2022099692A1 WO 2022099692 A1 WO2022099692 A1 WO 2022099692A1 CN 2020129058 W CN2020129058 W CN 2020129058W WO 2022099692 A1 WO2022099692 A1 WO 2022099692A1
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chloro
fluorination
chlorination
assembly
trifluoromethylpyridine
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PCT/CN2020/129058
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French (fr)
Chinese (zh)
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查志雄
郭永丽
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单县欣润化工有限公司
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/61—Halogen atoms or nitro radicals
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
    • B01D3/009—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping in combination with chemical reactions
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
    • B01D3/02—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping in boilers or stills
    • 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
    • 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
    • B01J19/0053—Details of the reactor
    • 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
    • B01J19/0053—Details of the reactor
    • B01J19/0073—Sealings
    • 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
    • B01J4/007—Feed or outlet devices as such, e.g. feeding tubes provided with moving parts
    • 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
    • B01J4/008—Feed or outlet control devices
    • 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
    • B01J2204/00—Aspects relating to feed or outlet devices; Regulating devices for feed or outlet devices
    • B01J2204/002—Aspects relating to feed or outlet devices; Regulating devices for feed or outlet devices the feeding side being of particular interest
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00162—Controlling or regulating processes controlling the pressure

Definitions

  • the invention relates to the technical field of chemical synthesis, in particular to a method and system for synthesizing 2-chloro-5-trifluoromethylpyridine.
  • 2-Chloro-5-trifluoromethylpyridine is a chemical substance whose appearance and properties are white semi-solids, mainly used in the production of agricultural chemicals such as diflufenacil and pharmaceuticals.
  • 2-Chloro-5-trifluoromethylpyridine products are generally stored in a cool and ventilated warehouse, and should be stored separately from oxidants and edible chemicals, and should not be stored together.
  • 3-methylpyridine is usually used as a raw material for chlorination to obtain 2-chloro-5-trichloromethylpyridine, and then further fluorination is performed to obtain 2-chloro-5-trichloromethylpyridine.
  • the product can be obtained; 3-methylpyridine can also be used as a raw material, and the product can be obtained by fluorination in the presence of a catalyst.
  • the technical solution adopted in the present invention is: a method for synthesizing 2-chloro-5-trifluoromethylpyridine, comprising the following steps: S1: preparing raw materials: adding N-oxy-3-methylpyridine The base pyridine raw material is put into the product synthesis system, and the catalyst is put into the product synthesis system at the same time; S2: chlorination reaction: benzoyl chloride is continued to be put into the above product synthesis system, and 2-chloro-5-methylpyridine is generated through the chlorination reaction S3: drop into initiator, sufficient catalyzer in the 2-chloro-5-methylpyridine product of above-mentioned gained, and control the initiation reaction to obtain the first product 2-chloro-5-trichloromethylpyridine; S4: by the above-mentioned The resultant is rectified and purified to obtain a fine 2-chloro-5-trichloromethylpyridine; S5: secondary separation and purification of 2-chloro-5
  • the catalyst in S3 is used as a phase transfer catalyst
  • the catalyst in S4 is one of cetyltrimethylammonium bromide or tetrabutylammonium bromide.
  • the reaction temperature of the fluorination reaction is -20--10°C, and the reaction time is 36-48h.
  • the initiator in the step S3 is cyclohexanone peroxide.
  • the catalyst in the step S1 is antimony pentoxide or aluminum oxide.
  • the weight ratio of 2-chloro-5-trichloromethylpyridine and iodine pentafluoride in the step S6 is 5-10:1.
  • a 2-chloro-5-trifluoromethylpyridine synthesis system is the product synthesis system described in any one of claims 1-6, including the following Step: comprising a sealed chlorination reaction kettle assembly, a fluorination reaction kettle assembly is connected to the chlorination reaction kettle assembly downstream of the chlorination reaction kettle assembly, and the chlorination reaction kettle assembly is connected with the chlorination reaction kettle assembly.
  • a purification treatment assembly is arranged between the chlorination reaction kettle components, and a chlorination feed treatment mechanism and a fluorination feed treatment mechanism are respectively provided on the top of the chlorination reaction kettle assembly and the fluorination reaction kettle assembly.
  • the chlorinated feed processing mechanism is used to achieve qualified particle size treatment and transport it to the inside of the chlorination reactor assembly
  • the fluorinated feed processing mechanism is used to achieve qualified material particle size treatment and transport it to the Inside the fluorination reaction kettle assembly
  • a product purification assembly is arranged at the discharge port of the fluorination reaction kettle assembly.
  • the chlorination reaction kettle assembly includes a sealed chlorination reaction kettle body, and the top of the chlorination reaction kettle body is provided with a first pressure gauge, a first temperature controller, a first inspection port, a chlorine A chlorination feed port, the top of the chlorination feed port is connected to the output end of the chlorination feed treatment mechanism, and the discharge port of the chlorination reaction kettle body is connected to the inlet of the purification treatment component.
  • the fluorination reaction kettle assembly includes a sealed fluorination reaction kettle body, and the top of the fluorination reaction kettle body is provided with a second pressure gauge, a second temperature controller, a second inspection port, a second A fluorinated feed port, a second fluorinated feed port, the top of the first fluorinated feed port is connected to the discharge port of the fluorinated feed processing mechanism, the second fluorinated feed port
  • the port is connected with the outlet of the purification treatment assembly, and the outlet of the fluorination reaction kettle body is connected with the inlet of the product purification assembly.
  • the purification treatment assembly includes a distillation still connected to the outlet of the chlorination reaction still body and used for receiving the first product 2-chloro-5-trichloromethylpyridine output from the chlorination reaction still body, A primary purification device is connected downstream of the distillation still, and a secondary purification device is connected downstream of the primary purification device. The outlet of the secondary purification device is connected to the second fluorination inlet of the fluorination reactor body. The feed port is connected.
  • the product purification assembly includes a recrystallization purification device, the inlet of the recrystallization purification device is connected to the outlet of the fluorination reaction kettle body.
  • a control valve is installed at each outlet and inlet position, and the materials conveyed between the adjacent components are powered by a power pump.
  • the chlorinated feed treatment mechanism and the fluorinated feed treatment mechanism are feed treatment mechanisms with the same structure, and the feed treatment mechanism includes an inclined rectangular feed pipe.
  • the feed port of the feed pipe is higher than the discharge port of the rectangular feed pipe, and the discharge port of the rectangular feed pipe is communicated with the first fluorination feed port of the fluorination reaction kettle body.
  • a pair of roller feeding assemblies are installed in the rectangular feeding tube, and the pairing roller feeding assemblies are used to control the feeding speed.
  • the feeding control assembly, the pair of roller feeding assembly and the fine feeding control assembly respectively provide driving power through two first feeding motors and two second feeding motors;
  • the second feeding motors are all fixedly installed on the outer side wall of the rectangular feeding pipe.
  • the pair of roller feeding components includes two oppositely arranged feeding rollers, and between the opposite side walls of the two feeding rollers is provided a crushing and blanking space for controlling the falling of materials, and each of the feeding rollers is located at a corresponding position.
  • the motor shaft of the first feeding motor is connected.
  • the fine feeding control assembly includes two abrasive rollers arranged opposite to each other, the two abrasive rollers are respectively arranged below the feeding roller, and the two abrasive rollers are comminuted by the feeding rollers through opposite rotation.
  • the latter material is extruded and fed, and each of the abrasive rollers is respectively connected with the motor shaft of the second feeding motor at the corresponding position.
  • This method utilizes N-oxygen-3-methylpyridine as a raw material to prepare 2-chloro-5-trifluoromethylpyridine, and the source of the raw material is easy and the cost is relatively low;
  • this method adopts a combination of chlorination reaction and fluorination reaction to obtain a product, and through efficient purification, the yield and quality of the product can be guaranteed;
  • the state of the material is not limited when the material is input.
  • the 2-chloro-5-trifluoromethylpyridine synthesis system can quickly realize the crushing and quantitative input of the material to ensure the effective control of the reaction components.
  • FIG. 1 is a partial cross-sectional structural schematic diagram of the present invention.
  • FIG. 2 is a schematic structural diagram of the installation position relationship of the roller feeding assembly of the present invention.
  • FIG. 3 is a schematic structural diagram of the installation position relationship of the fine feed control assembly of the present invention.
  • 1 chlorination reactor assembly 101, chlorination reactor body; 102, the first pressure gauge; 103, the first thermostat; 104, the first inspection port; 105, the chlorination feed port; 2, Fluorination reactor assembly; 201, fluorination reactor body; 202, second pressure gauge; 203, second thermostat; 204, second inspection port; 205, first fluorination feed port; 206, second Fluorination feed inlet; 3. Purification processing components; 301, Distillation kettle; 302, Primary purification equipment; 303, Secondary purification equipment; 4. Chlorination feed processing mechanism; 5. Fluorination feed processing mechanism; 6. Product purification components; 601, recrystallization and purification equipment; 7, rectangular feed pipe; 8, roller feeding components; 801, feeding rollers; 9, fine feeding control components; 901, abrasive rollers; 10, first feeding 11. The second feeding motor.
  • a method for synthesizing 2-chloro-5-trifluoromethylpyridine includes the following steps: S1: preparing raw materials: putting N-oxy-3-methylpyridine raw materials into the product synthesis system , put into the product synthesis system simultaneously; S2: chlorination reaction: continue to drop into benzoyl chloride in above-mentioned product synthesis system, produce 2-chloro-5-picoline through chlorination reaction; S3: to above-mentioned gained 2 - put initiator and sufficient catalyst into the chloro-5-methylpyridine product, and control the initiation reaction to obtain the first product 2-chloro-5-trichloromethylpyridine; S4: after rectifying and purifying the above-mentioned result Obtained fine 2-chloro-5-trichloromethylpyridine; S5: Secondary separation and purification of 2-chloro-5-trichloromethylpyridine for use -5-trichloromethylpyridine, iodine pentafluoride, and accelerator
  • 2-chloro-5-trifluoromethylpyridine is prepared by using N-oxy-3-methylpyridine as raw material.
  • the source of raw materials is easy and the cost is low.
  • the product is obtained by combining chlorination reaction and fluorination reaction. Purification can ensure the yield and quality of the product, and the use of multiple purification operations in the purification process can effectively ensure the purity of the obtained product.
  • the catalyst in S3 is used as a phase transfer catalyst
  • the catalyst in S4 is one of cetyltrimethylammonium bromide or tetrabutylammonium bromide.
  • the reaction temperature of the fluorination reaction is -20--10°C
  • the reaction time is 36-48 h, and the sufficiency of the reaction can be better ensured by controlling the reaction temperature and time.
  • the initiator in the step S3 is cyclohexanone peroxide.
  • the catalyst in the step S1 is antimony pentoxide or aluminum oxide.
  • the weight ratio of 2-chloro-5-trichloromethylpyridine and iodine pentafluoride in the step S6 is 5-10:1.
  • a 2-chloro-5-trifluoromethylpyridine synthesis system is the product synthesis system described in any one of claims 1-6, wherein It includes a chlorination reaction kettle assembly 1 with a sealed arrangement, and a fluorination reaction kettle assembly 2 is connected to the chlorination reaction kettle assembly 1 downstream of the chlorination reaction kettle assembly 1.
  • a purification treatment assembly 3 is arranged between the kettle assembly 1 and the chlorination reaction kettle assembly 1, and a chlorination feed treatment mechanism is respectively provided on the top of the chlorination reaction kettle assembly 1 and the fluorination reaction kettle assembly 2 4.
  • the fluorination feed processing mechanism 5, the chlorination feed processing mechanism 4 is used to realize that the particle size of the material is qualified and transported to the inside of the chlorination reactor assembly 1, and the fluorination feed processing mechanism 5 is used for After the particle size of the material is qualified and transported to the inside of the fluorination reactor assembly 2 , a product purification assembly 6 is provided at the discharge port of the fluorination reactor assembly 2 .
  • the materials entering the chlorination reactor assembly 1 through the chlorination feed processing mechanism 4 can be quickly pulverized to ensure the reaction efficiency after the materials enter.
  • an intermediate product can be obtained inside the fluorination reactor assembly 2, and then the intermediate product is purified by the purification treatment assembly 3 as a raw material for the next reaction, and a sufficient reaction is carried out in the fluorination reactor assembly 2. , and finally the desired product is processed by the product purification assembly 6 to realize the final product.
  • the materials entering the fluorination reactor assembly 2 through the fluorination feed processing mechanism 5 can also be pulverized to different degrees as required, which is beneficial to The full contact with other materials in the subsequent reaction improves the reaction efficiency.
  • the chlorination reaction kettle assembly 1 includes a sealed chlorination reaction kettle body 101, and a first pressure gauge 102, a first temperature controller 103, a first pressure gauge 102, a first temperature controller 103, a first pressure gauge 102, a first An inspection port 104, a chlorination feed port 105, the top of the chlorination feed port 105 is connected to the output end of the chlorination feed processing mechanism 4, and the discharge port of the chlorination reaction kettle body 101 It is connected to the inlet of the purification processing assembly 3 .
  • the temperature and air pressure inside the chlorination reaction kettle body 101 can be controlled by the first pressure gauge 102 and the first temperature controller 103, thereby ensuring the high efficiency of the reaction.
  • the fluorination reaction kettle assembly 2 includes a sealed fluorination reaction kettle body 201, and a second pressure gauge 202, a second temperature controller 203, a second pressure gauge 202, a second temperature controller 203, a second pressure gauge 202, a second temperature controller 203, Two inspection ports 204, a first fluorination feed port 205, a second fluorination feed port 206, the top of the first fluoride feed port 205 is in phase with the discharge port of the fluoride feed treatment mechanism 5 connected, the second fluorination feed port 206 is connected to the outlet of the purification processing assembly 3 , and the outlet of the fluorination reaction kettle body 201 is connected to the inlet of the product purification assembly 6 .
  • the temperature and air pressure inside the fluorination reaction kettle body 201 can be controlled by the second pressure gauge 202 and the second temperature controller 203, thereby ensuring the high efficiency of the reaction.
  • the purification treatment assembly 3 includes a device connected to the outlet of the chlorination reaction still body 101 and used for receiving the first product 2-chloro-5-trichloromethylpyridine output from the chlorination reaction still body 101
  • the distillation still 301 is connected with a primary purification device 302 downstream of the distillation still 301, and a secondary purification device 303 is connected downstream of the primary purification device 302.
  • the second fluorination feed port 206 of the reactor body 201 is connected.
  • the product purification assembly 6 includes a recrystallization and purification device 601 , and the inlet of the recrystallization and purification device 601 is connected to the outlet of the fluorination reactor body 201 .
  • Purification and filtration can be achieved by means of recrystallization, which can effectively improve the purity of the obtained product.
  • a control valve (not shown in the figure) is installed at each outlet and inlet position, and the materials conveyed between the adjacent components are powered by a power pump (not shown in the figure) to ensure material transfer. of fluency.
  • the chlorinated feed treatment mechanism 4 and the fluorinated feed treatment mechanism 5 are feed treatment mechanisms with the same structure, and the feed treatment mechanism includes a rectangular feed pipe 7 arranged obliquely.
  • the feed port of the rectangular feed pipe 7 is higher than the discharge port of the rectangular feed pipe 7, and the discharge port of the rectangular feed pipe 7 is connected to the first fluorination feed of the fluorination reactor body 201.
  • the feeding port 205 is communicated with each other.
  • a pair of roller feeding assemblies 8 are installed in the rectangular feeding pipe 7. The pairing roller feeding assemblies 8 are used to control the feeding speed.
  • a fine feeding control assembly 9 is installed in the rectangular feeding pipe 7 at the lower part of the lower part, and the pair of roller feeding assembly 8 and the fine feeding control assembly 9 are respectively driven by two first feeding motors 10, two The second feeding motor 11 provides driving power; the two first feeding motors 10 and the two second feeding motors 11 are fixedly installed on the outer wall of the rectangular feeding pipe 7 .
  • the feeding processing mechanism can quickly squeeze and pulverize the inserted granules or block materials through the roller feeding assembly 8, so as to ensure that the incoming materials can be fully pulverized and improve the material reaction effect and efficiency.
  • the roller feeding component 8 is preliminarily crushed by the rollers, and the fine feeding control component 9 realizes secondary abrasive crushing, thereby further improving the crushing fineness and effect, and realizing the input of ultra-fine crushed materials.
  • the pair of roller feeding assembly 8 includes two oppositely arranged feeding rollers 801, and between the opposite side walls of the two feeding rollers 801 is provided a crushing and blanking space for controlling the falling of materials, and each of the feeding rollers 801 is respectively It is connected to the motor shaft of the first feeding motor 10 at the corresponding position.
  • the fine feeding control assembly 9 includes two abrasive rollers 901 arranged opposite to each other, the two abrasive rollers 901 are respectively arranged below the feeding roller 801, and the two abrasive rollers 901 are opposite to each other through counter-rotation.
  • the pulverized materials by the above-mentioned feeding rollers 801 are extruded and fed, and each of the abrasive rollers 901 is respectively connected with the motor shaft of the second feeding motor 11 at the corresponding position.
  • Each feeding roller 801 and abrasive roller 901 are independently controlled by power, which can more effectively ensure the sufficiency of power.
  • each first feeding motor 10 and second feeding motor 11 can realize forward and reverse rotation.
  • the impurity can be controlled to reverse the rotation of the corresponding first feeding motor 10 to achieve material discharge and reduce damage to the feeding roller 801 .

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pyridine Compounds (AREA)

Abstract

The present invention relates to the technical field of chemical synthesis, and particularly, to a method and system for synthesizing 2-chloro-5-trifluoromethyl pyridine. The method comprises the following steps: S1: preparing raw materials; S2: carrying out a chlorination reaction; S3: adding an initiator and sufficient catalyst to a 2-chloro-5-methylpyridine product obtained from the above steps, and controlling an initiation reaction to obtain a crude 2-chloro-5-trichloromethyl pyridine; S4: distilling and purifying the product from above steps to obtain a refined 2-chloro-5-trichloromethyl pyridine; S5: separating and purifying, for the second time, the 2-chloro-5-trichloromethyl pyridine to be used; S6: carrying out a fluorination reaction; S7: transferring the crude solution to a downstream process of a product synthesis system for purification, and obtaining a refined 2-chloro-5-trifluoromethyl pyridine. The present method uses a combination of a chlorination reaction and a fluorination reaction in the synthesis of 2-chloro-5-trifluoromethyl pyridine to obtain the product, and also ensures product yield and quality by means of efficient purification.

Description

一种2-氯-5-三氟甲基吡啶合成方法及系统A kind of 2-chloro-5-trifluoromethylpyridine synthesis method and system 技术领域technical field
本发明涉及化学合成技术领域，尤其是一种2-氯-5-三氟甲基吡啶合成方法及系统。The invention relates to the technical field of chemical synthesis, in particular to a method and system for synthesizing 2-chloro-5-trifluoromethylpyridine.
背景技术Background technique
2-氯-5-三氟甲基吡啶是一种化学物质，其外观与性状为白色半固体，主要用于农用化学品如精吡氟禾草灵和医药品的生产。2-氯-5-三氟甲基吡啶产品一般储存于阴凉、通风的库房，应与氧化剂、食用化学品分开存放，切忌混储。2-Chloro-5-trifluoromethylpyridine is a chemical substance whose appearance and properties are white semi-solids, mainly used in the production of agricultural chemicals such as diflufenacil and pharmaceuticals. 2-Chloro-5-trifluoromethylpyridine products are generally stored in a cool and ventilated warehouse, and should be stored separately from oxidants and edible chemicals, and should not be stored together.
目前在进行2-氯-5-三氟甲基吡啶的合成时通常采用以3-甲基吡啶为原料先进行氯化得2-氯-5-三氯甲基吡啶,再进一步进行氟化而得到产品；也可以用3-甲基吡啶为原料,在催化剂存在下进行氟氯化反应而得到产品。At present, when synthesizing 2-chloro-5-trifluoromethylpyridine, 3-methylpyridine is usually used as a raw material for chlorination to obtain 2-chloro-5-trichloromethylpyridine, and then further fluorination is performed to obtain 2-chloro-5-trichloromethylpyridine. The product can be obtained; 3-methylpyridine can also be used as a raw material, and the product can be obtained by fluorination in the presence of a catalyst.
利用现有的方法制备2-氯-5-三氟甲基吡啶时通常存在产率低，合成反应后的产物分离提纯率低，排放存在大量污染物的问题，因此现有的制备2-氯-5-三氟甲基吡啶的合成方法不能有效地满足越来越高的生产要求。When using the existing method to prepare 2-chloro-5-trifluoromethylpyridine, the yield is usually low, the separation and purification rate of the product after the synthesis reaction is low, and there are a large number of pollutants in the discharge. Therefore, the existing preparation of 2-chloro The synthesis method of -5-trifluoromethylpyridine cannot effectively meet the increasingly high production requirements.
发明内容SUMMARY OF THE INVENTION
本发明为解决上述技术问题之一，所采用的技术方案是：一种2-氯-5-三氟甲基吡啶合成方法，包括如下步骤：S1：准备原料：将N-氧-3-甲基吡啶原料投入产品合成系统内部，同时投入催化剂至产品合成系统内部；S2：氯化反应：向上述产品合成系统内继续投入苯甲酰氯，经过氯化反应产生2-氯-5-甲基吡啶；S3：向上述所得的2-氯-5-甲基吡啶产品中投入引发剂、充足的催化剂，并控制引发反应得到初品2-氯-5-三氯甲基吡啶；S4：通过对上述所得物进行精馏并提纯后得到精品2-氯-5-三氯甲基吡啶；S5：二次分离提纯2-氯-5-三氯甲基吡啶待用S6：氟化反应：将上述二次分离提纯后的2-氯-5-三氯甲基吡啶、五氟化碘、促进剂投入至合成系统内进行氟化反应，得含有2-氯-5-三氟甲基吡啶的粗品溶液；S7：将粗品溶液转入产品合成系统内部的下游工序进行纯化，得到精品2-氯-5-三氟甲基吡啶。In order to solve one of the above technical problems, the technical solution adopted in the present invention is: a method for synthesizing 2-chloro-5-trifluoromethylpyridine, comprising the following steps: S1: preparing raw materials: adding N-oxy-3-methylpyridine The base pyridine raw material is put into the product synthesis system, and the catalyst is put into the product synthesis system at the same time; S2: chlorination reaction: benzoyl chloride is continued to be put into the above product synthesis system, and 2-chloro-5-methylpyridine is generated through the chlorination reaction S3: drop into initiator, sufficient catalyzer in the 2-chloro-5-methylpyridine product of above-mentioned gained, and control the initiation reaction to obtain the first product 2-chloro-5-trichloromethylpyridine; S4: by the above-mentioned The resultant is rectified and purified to obtain a fine 2-chloro-5-trichloromethylpyridine; S5: secondary separation and purification of 2-chloro-5-trichloromethylpyridine for use S6: fluorination reaction: the above two The 2-chloro-5-trichloromethylpyridine, iodine pentafluoride and accelerator after the first separation and purification are put into the synthesis system to carry out fluorination reaction to obtain a crude product solution containing 2-chloro-5-trifluoromethylpyridine ; S7: the crude product solution is transferred to the downstream process inside the product synthesis system for purification to obtain the fine 2-chloro-5-trifluoromethylpyridine.
优选地，所述S3中的催化剂作为相转移催化剂使用，所述S4中的催化剂为十六烷基三甲基溴化铵或四丁基溴化铵中的一种。Preferably, the catalyst in S3 is used as a phase transfer catalyst, and the catalyst in S4 is one of cetyltrimethylammonium bromide or tetrabutylammonium bromide.
优选地，所述氟化反应的反应温度为-20～-10℃、反应时间为36-48h。Preferably, the reaction temperature of the fluorination reaction is -20--10°C, and the reaction time is 36-48h.
优选地，所述S3步骤中的引发剂采用过氧化环己酮。Preferably, the initiator in the step S3 is cyclohexanone peroxide.
优选地，所述S1步骤中的催化剂为五氧化二锑或三氧化二铝。Preferably, the catalyst in the step S1 is antimony pentoxide or aluminum oxide.
优选地，所述S6步骤中的2-氯-5-三氯甲基吡啶、五氟化碘的重量比为5-10：1。Preferably, the weight ratio of 2-chloro-5-trichloromethylpyridine and iodine pentafluoride in the step S6 is 5-10:1.
一种2-氯-5-三氟甲基吡啶合成系统，所述2-氯-5-三氟甲基吡啶合成系统为权利要求1-6中任意一项所述的产品合成系统，包括如下步骤：包括一密封设置的氯化反应釜组件，在所述氯化反应釜组件，在所述氯化反应釜组件的下游连接有一氟化反应釜组件，在所述氯化反应釜组件与所述氯化反应釜组件之间设有一提纯处理组件，在所述氯化反应釜组件、所述氟化反应釜组件的顶部分别设置有一氯化进料处理机构、氟化进料处理机构，所述氯化进料处理机构用于实现将物料粒径处理合格后并输送至氯化反应釜组件内部，所述氟化进料处理机构用于实现将物料粒径处理合格后并输送至所述氟化反应釜组件内部，在所述氟化反应釜组件的出料口设置有一产品纯化组件。A 2-chloro-5-trifluoromethylpyridine synthesis system, the 2-chloro-5-trifluoromethylpyridine synthesis system is the product synthesis system described in any one of claims 1-6, including the following Step: comprising a sealed chlorination reaction kettle assembly, a fluorination reaction kettle assembly is connected to the chlorination reaction kettle assembly downstream of the chlorination reaction kettle assembly, and the chlorination reaction kettle assembly is connected with the chlorination reaction kettle assembly. A purification treatment assembly is arranged between the chlorination reaction kettle components, and a chlorination feed treatment mechanism and a fluorination feed treatment mechanism are respectively provided on the top of the chlorination reaction kettle assembly and the fluorination reaction kettle assembly. The chlorinated feed processing mechanism is used to achieve qualified particle size treatment and transport it to the inside of the chlorination reactor assembly, and the fluorinated feed processing mechanism is used to achieve qualified material particle size treatment and transport it to the Inside the fluorination reaction kettle assembly, a product purification assembly is arranged at the discharge port of the fluorination reaction kettle assembly.
优选地，所述氯化反应釜组件包括一密封设置的氯化反应釜体，在所述氯化反应釜体的顶部设置有第一压力表、第一温控器、第一检修口、氯化进料口，所述氯化进料口的顶部与所述氯化进料处理机构的输出端相连接，所述氯化反应釜体的出料口与所述提纯处理组件的进口相连。Preferably, the chlorination reaction kettle assembly includes a sealed chlorination reaction kettle body, and the top of the chlorination reaction kettle body is provided with a first pressure gauge, a first temperature controller, a first inspection port, a chlorine A chlorination feed port, the top of the chlorination feed port is connected to the output end of the chlorination feed treatment mechanism, and the discharge port of the chlorination reaction kettle body is connected to the inlet of the purification treatment component.
优选地，所述氟化反应釜组件包括一密封设置的氟化反应釜体，在所述氟化反应釜体的顶部设置有第二压力表、第二温控器、第二检修口、第一氟化进料口、第二氟化进料口，所述第一氟化进料口的顶部与所述氟化进料处理机构的出料口相连接，所述第二氟化进料口与所述提纯处理组件的出口相连，所述氟化反应釜体的出口与所述产品纯化组件的进口相连。Preferably, the fluorination reaction kettle assembly includes a sealed fluorination reaction kettle body, and the top of the fluorination reaction kettle body is provided with a second pressure gauge, a second temperature controller, a second inspection port, a second A fluorinated feed port, a second fluorinated feed port, the top of the first fluorinated feed port is connected to the discharge port of the fluorinated feed processing mechanism, the second fluorinated feed port The port is connected with the outlet of the purification treatment assembly, and the outlet of the fluorination reaction kettle body is connected with the inlet of the product purification assembly.
优选地，所述提纯处理组件包括一与所述氯化反应釜体的出口相连接并用于接收来自氯化反应釜体输出的初品2-氯-5-三氯甲基吡啶的蒸馏釜，在所述蒸馏釜的下游连接有一次提纯设备，在所述一次提纯设备的下游连接有二次提纯设备，所述二次提纯设备的出口与所述氟化反应釜体的第二氟化进料口相连。Preferably, the purification treatment assembly includes a distillation still connected to the outlet of the chlorination reaction still body and used for receiving the first product 2-chloro-5-trichloromethylpyridine output from the chlorination reaction still body, A primary purification device is connected downstream of the distillation still, and a secondary purification device is connected downstream of the primary purification device. The outlet of the secondary purification device is connected to the second fluorination inlet of the fluorination reactor body. The feed port is connected.
优选地，产品纯化组件包括一重结晶纯化设备，所述重结晶纯化设备的进口与所述氟化反应釜体的出口相连。Preferably, the product purification assembly includes a recrystallization purification device, the inlet of the recrystallization purification device is connected to the outlet of the fluorination reaction kettle body.
优选地，在各出口与进口位置处均安装有控制阀，各相连相邻的零部件之间输送物料通过动力泵提供动力。Preferably, a control valve is installed at each outlet and inlet position, and the materials conveyed between the adjacent components are powered by a power pump.
优选地，所述氯化进料处理机构与所述氟化进料处理机构为结构相同的进料处理机构，所述进料处理机构包括一倾斜设置的矩形进料管，在所述矩形进料管的进料口高于所述矩形进料管的出料口，所述矩形进料管的出料口与所述氟化反应釜体的第一氟化进料口相连通设置，在所述矩形进料管内安装有一对辊进料组件，所述对辊进料组件用于实现控制进料 速度，在所述对辊进料组件的下部的所述矩形进料管内安装有一精细进料控制组件，所述对辊进料组件、所述精细进料控制组件分别通过两个第一进料电机、两个第二进料电机提供驱动动力；两所述第一进料电机、两所述第二进料电机均固定安装在所述矩形进料管的外侧壁上。Preferably, the chlorinated feed treatment mechanism and the fluorinated feed treatment mechanism are feed treatment mechanisms with the same structure, and the feed treatment mechanism includes an inclined rectangular feed pipe. The feed port of the feed pipe is higher than the discharge port of the rectangular feed pipe, and the discharge port of the rectangular feed pipe is communicated with the first fluorination feed port of the fluorination reaction kettle body. A pair of roller feeding assemblies are installed in the rectangular feeding tube, and the pairing roller feeding assemblies are used to control the feeding speed. The feeding control assembly, the pair of roller feeding assembly and the fine feeding control assembly respectively provide driving power through two first feeding motors and two second feeding motors; The second feeding motors are all fixedly installed on the outer side wall of the rectangular feeding pipe.
所述对辊进料组件包括两相对设置的进料辊，两所述进料辊的相对侧壁之间设置有控制物料落下的粉碎下料空间，各所述进料辊分别于对应位置处的所述第一进料电机的电机轴相连。The pair of roller feeding components includes two oppositely arranged feeding rollers, and between the opposite side walls of the two feeding rollers is provided a crushing and blanking space for controlling the falling of materials, and each of the feeding rollers is located at a corresponding position. The motor shaft of the first feeding motor is connected.
优选地，所述精细进料控制组件包括两相对设置的磨料辊，两所述磨料辊分别设置在所述进料辊的下方，两所述磨料辊通过对转实现对被上述进料辊粉碎后的物料进行挤料进料，各所述磨料辊分别与对应位置处的所述第二进料电机的电机轴相连。Preferably, the fine feeding control assembly includes two abrasive rollers arranged opposite to each other, the two abrasive rollers are respectively arranged below the feeding roller, and the two abrasive rollers are comminuted by the feeding rollers through opposite rotation. The latter material is extruded and fed, and each of the abrasive rollers is respectively connected with the motor shaft of the second feeding motor at the corresponding position.
本发明的有益效果体现在：The beneficial effects of the present invention are embodied in:
1、本法利用N-氧-3-甲基吡啶为原料制备2-氯-5-三氟甲基吡啶，原料来源容易，成本较低；1. This method utilizes N-oxygen-3-methylpyridine as a raw material to prepare 2-chloro-5-trifluoromethylpyridine, and the source of the raw material is easy and the cost is relatively low;
2、本法在合成2-氯-5-三氟甲基吡啶的过程中采用氯化反应、氟化反应结合获得产品，并经过高效提纯，能够保证产品的产率与质量；2. In the process of synthesizing 2-chloro-5-trifluoromethylpyridine, this method adopts a combination of chlorination reaction and fluorination reaction to obtain a product, and through efficient purification, the yield and quality of the product can be guaranteed;
3、在进行物料的投入时不限制材料的状态，通过2-氯-5-三氟甲基吡啶合成系统能够快速的实现粉碎、定量的投入物料，保证反应组分的有效控制。3. The state of the material is not limited when the material is input. The 2-chloro-5-trifluoromethylpyridine synthesis system can quickly realize the crushing and quantitative input of the material to ensure the effective control of the reaction components.
附图说明Description of drawings
为了更清楚地说明本发明具体实施方式或现有技术中的技术方案，下面将对具体实施方式或现有技术描述中所需要使用的附图作简单地介绍。在所有附图中，类似的元件或部件一般由类似的附图标记标识。附图中，各元件或部件并不一定按照实际的比例绘制。In order to illustrate the specific embodiments of the present invention or the technical solutions in the prior art more clearly, the following briefly introduces the accompanying drawings that are required to be used in the description of the specific embodiments or the prior art. Similar elements or components are generally identified by similar reference numerals throughout the drawings. In the drawings, each element or component is not necessarily drawn to actual scale.
图1为本发明的局部剖视结构示意图。FIG. 1 is a partial cross-sectional structural schematic diagram of the present invention.
图2为本发明的对辊进料组件的安装位置关系结构示意图。FIG. 2 is a schematic structural diagram of the installation position relationship of the roller feeding assembly of the present invention.
图3为本发明的精细进料控制组件的安装位置关系结构示意图。FIG. 3 is a schematic structural diagram of the installation position relationship of the fine feed control assembly of the present invention.
图中，1氯化反应釜组件；101、氯化反应釜体；102、第一压力表；103、第一温控器；104、第一检修口；105、氯化进料口；2、氟化反应釜组件；201、氟化反应釜体；202、第二压力表；203、第二温控器；204、第二检修口；205、第一氟化进料口；206、第二氟化进料口；3、提纯处理组件；301、蒸馏釜；302、一次提纯设备；303、二次提纯设备；4、氯化进料处理机构；5、氟化进料处理机构；6、产品纯化组件；601、重结晶纯化设备；7、矩形进料管；8、对辊进料组件；801、进料辊；9、精细进料控制组件；901、磨料 辊；10、第一进料电机；11、第二进料电机。In the figure, 1 chlorination reactor assembly; 101, chlorination reactor body; 102, the first pressure gauge; 103, the first thermostat; 104, the first inspection port; 105, the chlorination feed port; 2, Fluorination reactor assembly; 201, fluorination reactor body; 202, second pressure gauge; 203, second thermostat; 204, second inspection port; 205, first fluorination feed port; 206, second Fluorination feed inlet; 3. Purification processing components; 301, Distillation kettle; 302, Primary purification equipment; 303, Secondary purification equipment; 4. Chlorination feed processing mechanism; 5. Fluorination feed processing mechanism; 6. Product purification components; 601, recrystallization and purification equipment; 7, rectangular feed pipe; 8, roller feeding components; 801, feeding rollers; 9, fine feeding control components; 901, abrasive rollers; 10, first feeding 11. The second feeding motor.
具体实施方式Detailed ways
下面将结合附图对本发明技术方案的实施例进行详细的描述。以下实施例仅用于更加清楚地说明本发明的技术方案，因此只作为示例，而不能以此来限制本发明的保护范围。Embodiments of the technical solutions of the present invention will be described in detail below with reference to the accompanying drawings. The following examples are only used to more clearly illustrate the technical solutions of the present invention, and are therefore only used as examples, and cannot be used to limit the protection scope of the present invention.
如图1-3中所示，一种2-氯-5-三氟甲基吡啶合成方法，包括如下步骤：S1：准备原料：将N-氧-3-甲基吡啶原料投入产品合成系统内部，同时投入催化剂至产品合成系统内部；S2：氯化反应：向上述产品合成系统内继续投入苯甲酰氯，经过氯化反应产生2-氯-5-甲基吡啶；S3：向上述所得的2-氯-5-甲基吡啶产品中投入引发剂、充足的催化剂，并控制引发反应得到初品2-氯-5-三氯甲基吡啶；S4：通过对上述所得物进行精馏并提纯后得到精品2-氯-5-三氯甲基吡啶；S5：二次分离提纯2-氯-5-三氯甲基吡啶待用S6：氟化反应：将上述二次分离提纯后的2-氯-5-三氯甲基吡啶、五氟化碘、促进剂投入至合成系统内进行氟化反应，得含有2-氯-5-三氟甲基吡啶的粗品溶液；S7：将粗品溶液转入产品合成系统内部的下游工序进行纯化，得到精品2-氯-5-三氟甲基吡啶。As shown in Figure 1-3, a method for synthesizing 2-chloro-5-trifluoromethylpyridine includes the following steps: S1: preparing raw materials: putting N-oxy-3-methylpyridine raw materials into the product synthesis system , put into the product synthesis system simultaneously; S2: chlorination reaction: continue to drop into benzoyl chloride in above-mentioned product synthesis system, produce 2-chloro-5-picoline through chlorination reaction; S3: to above-mentioned gained 2 - put initiator and sufficient catalyst into the chloro-5-methylpyridine product, and control the initiation reaction to obtain the first product 2-chloro-5-trichloromethylpyridine; S4: after rectifying and purifying the above-mentioned result Obtained fine 2-chloro-5-trichloromethylpyridine; S5: Secondary separation and purification of 2-chloro-5-trichloromethylpyridine for use -5-trichloromethylpyridine, iodine pentafluoride, and accelerator are put into the synthesis system to carry out fluorination reaction to obtain a crude product solution containing 2-chloro-5-trifluoromethylpyridine; S7: the crude product solution is transferred into The downstream process inside the product synthesis system is purified to obtain the fine 2-chloro-5-trifluoromethylpyridine.
在此利用N-氧-3-甲基吡啶为原料制备2-氯-5-三氟甲基吡啶，原料来源容易，成本较低，采用氯化反应、氟化反应结合获得产品，并经过高效提纯，能够保证产品的产率与质量，在纯化的工序中采用多次纯化的操作能够有效的保证所得产品的纯净度。Here, 2-chloro-5-trifluoromethylpyridine is prepared by using N-oxy-3-methylpyridine as raw material. The source of raw materials is easy and the cost is low. The product is obtained by combining chlorination reaction and fluorination reaction. Purification can ensure the yield and quality of the product, and the use of multiple purification operations in the purification process can effectively ensure the purity of the obtained product.
优选地，所述S3中的催化剂作为相转移催化剂使用，所述S4中的催化剂为十六烷基三甲基溴化铵或四丁基溴化铵中的一种。Preferably, the catalyst in S3 is used as a phase transfer catalyst, and the catalyst in S4 is one of cetyltrimethylammonium bromide or tetrabutylammonium bromide.
优选地，所述氟化反应的反应温度为-20～-10℃、反应时间为36-48h，控制反应温度与时间可以更好的保证反应的充分性。Preferably, the reaction temperature of the fluorination reaction is -20--10°C, and the reaction time is 36-48 h, and the sufficiency of the reaction can be better ensured by controlling the reaction temperature and time.
优选地，所述S3步骤中的引发剂采用过氧化环己酮。Preferably, the initiator in the step S3 is cyclohexanone peroxide.
优选地，所述S1步骤中的催化剂为五氧化二锑或三氧化二铝。Preferably, the catalyst in the step S1 is antimony pentoxide or aluminum oxide.
优选地，所述S6步骤中的2-氯-5-三氯甲基吡啶、五氟化碘的重量比为5-10：1。Preferably, the weight ratio of 2-chloro-5-trichloromethylpyridine and iodine pentafluoride in the step S6 is 5-10:1.
一种2-氯-5-三氟甲基吡啶合成系统，所述2-氯-5-三氟甲基吡啶合成系统为权利要求1-6中任意一项所述的产品合成系统，其特征在于：包括一密封设置的氯化反应釜组件1，在所述氯化反应釜组件1，在所述氯化反应釜组件1的下游连接有一氟化反应釜组件2，在所述氯化反应釜组件1与所述氯化反应釜组件1之间设有一提纯处理组件3，在所述氯化反应釜组件1、所述氟化反应釜组件2的顶部分别设置有一氯化进料处理机构4、氟化进料处理机构5，所述氯化进料处理机构4用于实现将物料粒径处理合格后并输送至氯化反应釜组件1内部，所述氟化进料处理机构5用于实现将物料粒径处理合格后并输送至所述氟化反应 釜组件2内部，在所述氟化反应釜组件2的出料口设置有一产品纯化组件6。A 2-chloro-5-trifluoromethylpyridine synthesis system, the 2-chloro-5-trifluoromethylpyridine synthesis system is the product synthesis system described in any one of claims 1-6, wherein It includes a chlorination reaction kettle assembly 1 with a sealed arrangement, and a fluorination reaction kettle assembly 2 is connected to the chlorination reaction kettle assembly 1 downstream of the chlorination reaction kettle assembly 1. In the chlorination reaction kettle assembly 1 A purification treatment assembly 3 is arranged between the kettle assembly 1 and the chlorination reaction kettle assembly 1, and a chlorination feed treatment mechanism is respectively provided on the top of the chlorination reaction kettle assembly 1 and the fluorination reaction kettle assembly 2 4. The fluorination feed processing mechanism 5, the chlorination feed processing mechanism 4 is used to realize that the particle size of the material is qualified and transported to the inside of the chlorination reactor assembly 1, and the fluorination feed processing mechanism 5 is used for After the particle size of the material is qualified and transported to the inside of the fluorination reactor assembly 2 , a product purification assembly 6 is provided at the discharge port of the fluorination reactor assembly 2 .
通过氯化进料处理机构4进入氯化反应釜组件1的物料可以快速的实现粉碎，保证物料进入后的反应效率。The materials entering the chlorination reactor assembly 1 through the chlorination feed processing mechanism 4 can be quickly pulverized to ensure the reaction efficiency after the materials enter.
同时控制反应温度与时间后可以使得氟化反应釜组件2内部得到中间产物，然后利用提纯处理组件3对中间产物进行提纯后作为下一反应的原料，在氟化反应釜组件2进行充分的反应，最终得到所需产品经过产品纯化组件6的处理来实现最终产品，同样的通过氟化进料处理机构5进入氟化反应釜组件2的物料也可以根据需要实现不同程度的粉碎，从而有利于后续反应中与其他物料的充分接触，提高反应效率。After simultaneously controlling the reaction temperature and time, an intermediate product can be obtained inside the fluorination reactor assembly 2, and then the intermediate product is purified by the purification treatment assembly 3 as a raw material for the next reaction, and a sufficient reaction is carried out in the fluorination reactor assembly 2. , and finally the desired product is processed by the product purification assembly 6 to realize the final product. Similarly, the materials entering the fluorination reactor assembly 2 through the fluorination feed processing mechanism 5 can also be pulverized to different degrees as required, which is beneficial to The full contact with other materials in the subsequent reaction improves the reaction efficiency.
优选地，所述氯化反应釜组件1包括一密封设置的氯化反应釜体101，在所述氯化反应釜体101的顶部设置有第一压力表102、第一温控器103、第一检修口104、氯化进料口105，所述氯化进料口105的顶部与所述氯化进料处理机构4的输出端相连接，所述氯化反应釜体101的出料口与所述提纯处理组件3的进口相连。Preferably, the chlorination reaction kettle assembly 1 includes a sealed chlorination reaction kettle body 101, and a first pressure gauge 102, a first temperature controller 103, a first pressure gauge 102, a first temperature controller 103, a first pressure gauge 102, a first An inspection port 104, a chlorination feed port 105, the top of the chlorination feed port 105 is connected to the output end of the chlorination feed processing mechanism 4, and the discharge port of the chlorination reaction kettle body 101 It is connected to the inlet of the purification processing assembly 3 .
通过第一压力表102、第一温控器103可以控制氯化反应釜体101内部的温度与气压，从而保证反应的高效性。The temperature and air pressure inside the chlorination reaction kettle body 101 can be controlled by the first pressure gauge 102 and the first temperature controller 103, thereby ensuring the high efficiency of the reaction.
优选地，所述氟化反应釜组件2包括一密封设置的氟化反应釜体201，在所述氟化反应釜体201的顶部设置有第二压力表202、第二温控器203、第二检修口204、第一氟化进料口205、第二氟化进料口206，所述第一氟化进料口205的顶部与所述氟化进料处理机构5的出料口相连接，所述第二氟化进料口206与所述提纯处理组件3的出口相连，所述氟化反应釜体201的出口与所述产品纯化组件6的进口相连。Preferably, the fluorination reaction kettle assembly 2 includes a sealed fluorination reaction kettle body 201, and a second pressure gauge 202, a second temperature controller 203, a second pressure gauge 202, a second temperature controller 203, a second pressure gauge 202, a second temperature controller 203, Two inspection ports 204, a first fluorination feed port 205, a second fluorination feed port 206, the top of the first fluoride feed port 205 is in phase with the discharge port of the fluoride feed treatment mechanism 5 connected, the second fluorination feed port 206 is connected to the outlet of the purification processing assembly 3 , and the outlet of the fluorination reaction kettle body 201 is connected to the inlet of the product purification assembly 6 .
通过第二压力表202、第二温控器203可以控制氟化反应釜体201内部的温度与气压，从而保证反应的高效性。The temperature and air pressure inside the fluorination reaction kettle body 201 can be controlled by the second pressure gauge 202 and the second temperature controller 203, thereby ensuring the high efficiency of the reaction.
优选地，所述提纯处理组件3包括一与所述氯化反应釜体101的出口相连接并用于接收来自氯化反应釜体101输出的初品2-氯-5-三氯甲基吡啶的蒸馏釜301，在所述蒸馏釜301的下游连接有一次提纯设备302，在所述一次提纯设备302的下游连接有二次提纯设备303，所述二次提纯设备303的出口与所述氟化反应釜体201的第二氟化进料口206相连。Preferably, the purification treatment assembly 3 includes a device connected to the outlet of the chlorination reaction still body 101 and used for receiving the first product 2-chloro-5-trichloromethylpyridine output from the chlorination reaction still body 101 The distillation still 301 is connected with a primary purification device 302 downstream of the distillation still 301, and a secondary purification device 303 is connected downstream of the primary purification device 302. The second fluorination feed port 206 of the reactor body 201 is connected.
在进行初品2-氯-5-三氯甲基吡啶的提纯时通过蒸馏与纯化可以有效的保证提纯的效果，使其满足使用需求。When purifying the first product 2-chloro-5-trichloromethylpyridine, distillation and purification can effectively ensure the effect of purification, so that it can meet the needs of use.
优选地，产品纯化组件6包括一重结晶纯化设备601，所述重结晶纯化设备601的进口与所述氟化反应釜体201的出口相连。Preferably, the product purification assembly 6 includes a recrystallization and purification device 601 , and the inlet of the recrystallization and purification device 601 is connected to the outlet of the fluorination reactor body 201 .
通过重结晶的方式实现提纯过滤，可以有效的提高所得产物的纯度。Purification and filtration can be achieved by means of recrystallization, which can effectively improve the purity of the obtained product.
优选地，在各出口与进口位置处均安装有控制阀(图中未示出)，各相连相邻的零部件之间输送物料通过动力泵(图中未示出)提供动力，保证物料转运的流畅性。Preferably, a control valve (not shown in the figure) is installed at each outlet and inlet position, and the materials conveyed between the adjacent components are powered by a power pump (not shown in the figure) to ensure material transfer. of fluency.
优选地，所述氯化进料处理机构4与所述氟化进料处理机构5为结构相同的进料处理机构，所述进料处理机构包括一倾斜设置的矩形进料管7，在所述矩形进料管7的进料口高于所述矩形进料管7的出料口，所述矩形进料管7的出料口与所述氟化反应釜体201的第一氟化进料口205相连通设置，在所述矩形进料管7内安装有一对辊进料组件8，所述对辊进料组件8用于实现控制进料速度，在所述对辊进料组件8的下部的所述矩形进料管7内安装有一精细进料控制组件9，所述对辊进料组件8、所述精细进料控制组件9分别通过两个第一进料电机10、两个第二进料电机11提供驱动动力；两所述第一进料电机10、两所述第二进料电机11均固定安装在所述矩形进料管7的外侧壁上。Preferably, the chlorinated feed treatment mechanism 4 and the fluorinated feed treatment mechanism 5 are feed treatment mechanisms with the same structure, and the feed treatment mechanism includes a rectangular feed pipe 7 arranged obliquely. The feed port of the rectangular feed pipe 7 is higher than the discharge port of the rectangular feed pipe 7, and the discharge port of the rectangular feed pipe 7 is connected to the first fluorination feed of the fluorination reactor body 201. The feeding port 205 is communicated with each other. A pair of roller feeding assemblies 8 are installed in the rectangular feeding pipe 7. The pairing roller feeding assemblies 8 are used to control the feeding speed. A fine feeding control assembly 9 is installed in the rectangular feeding pipe 7 at the lower part of the lower part, and the pair of roller feeding assembly 8 and the fine feeding control assembly 9 are respectively driven by two first feeding motors 10, two The second feeding motor 11 provides driving power; the two first feeding motors 10 and the two second feeding motors 11 are fixedly installed on the outer wall of the rectangular feeding pipe 7 .
进料处理机构通过对辊进料组件8可以实现对置入的颗粒或者块状的物料进行快速的挤压粉碎，从而保证进入的物料能够充分的粉碎，提高物料反应效果与效率。The feeding processing mechanism can quickly squeeze and pulverize the inserted granules or block materials through the roller feeding assembly 8, so as to ensure that the incoming materials can be fully pulverized and improve the material reaction effect and efficiency.
对辊进料组件8进行初步的对辊粉碎，精细进料控制组件9实现二次磨料粉碎，从而进一步的提高粉碎细度与效果，实现超细粉碎物料的投入。The roller feeding component 8 is preliminarily crushed by the rollers, and the fine feeding control component 9 realizes secondary abrasive crushing, thereby further improving the crushing fineness and effect, and realizing the input of ultra-fine crushed materials.
所述对辊进料组件8包括两相对设置的进料辊801，两所述进料辊801的相对侧壁之间设置有控制物料落下的粉碎下料空间，各所述进料辊801分别于对应位置处的所述第一进料电机10的电机轴相连。The pair of roller feeding assembly 8 includes two oppositely arranged feeding rollers 801, and between the opposite side walls of the two feeding rollers 801 is provided a crushing and blanking space for controlling the falling of materials, and each of the feeding rollers 801 is respectively It is connected to the motor shaft of the first feeding motor 10 at the corresponding position.
优选地，所述精细进料控制组件9包括两相对设置的磨料辊901，两所述磨料辊901分别设置在所述进料辊801的下方，两所述磨料辊901通过对转实现对被上述进料辊801粉碎后的物料进行挤料进料，各所述磨料辊901分别与对应位置处的所述第二进料电机11的电机轴相连。Preferably, the fine feeding control assembly 9 includes two abrasive rollers 901 arranged opposite to each other, the two abrasive rollers 901 are respectively arranged below the feeding roller 801, and the two abrasive rollers 901 are opposite to each other through counter-rotation. The pulverized materials by the above-mentioned feeding rollers 801 are extruded and fed, and each of the abrasive rollers 901 is respectively connected with the motor shaft of the second feeding motor 11 at the corresponding position.
各个进料辊801、磨料辊901均单独动力控制，可以更有效的保证动力的充足性，同时各个第一进料电机10、第二进料电机11可以实现正反转，当遇到无法粉碎的杂质是可以控制对应的第一进料电机10的旋转反向来实现吐料，减少对进料辊801的损坏。Each feeding roller 801 and abrasive roller 901 are independently controlled by power, which can more effectively ensure the sufficiency of power. At the same time, each first feeding motor 10 and second feeding motor 11 can realize forward and reverse rotation. The impurity can be controlled to reverse the rotation of the corresponding first feeding motor 10 to achieve material discharge and reduce damage to the feeding roller 801 .
以上各实施例仅用以说明本发明的技术方案，而非对其限制；尽管参照前述各实施例对本发明进行了详细的说明，本领域的普通技术人员应当理解：其依然可以对前述各实施例所记载的技术方案进行修改，或者对其中部分或者全部技术特征进行等同替换；而这些修改或者替换，并不使相应技术方案的本质脱离本发明各实施例技术方案的范围，其均应涵盖在本发明的权利要求和说明书的范围当中；对于本技术领域的技术人员来说，对本发明实施方式所做出的任何替代改进或变换均落在本发明的保护范围内。The above embodiments are only used to illustrate the technical solutions of the present invention, but not to limit them; although the present invention has been described in detail with reference to the foregoing embodiments, those of ordinary skill in the art should understand that the foregoing embodiments can still be used for The technical solutions described in the examples are modified, or some or all of the technical features thereof are equivalently replaced; and these modifications or replacements do not make the essence of the corresponding technical solutions deviate from the scope of the technical solutions of the embodiments of the present invention. Within the scope of the claims and description of the present invention; for those skilled in the art, any alternative improvements or transformations made to the embodiments of the present invention fall within the protection scope of the present invention.
本发明未详述之处，均为本技术领域技术人员的公知技术。The parts that are not described in detail in the present invention are the well-known technologies of those skilled in the art.

Claims (10)

  1. 一种2-氯-5-三氟甲基吡啶合成方法，其特征在于：包括如下步骤：A method for synthesizing 2-chloro-5-trifluoromethylpyridine, comprising the steps of:
    S1：准备原料：S1: Prepare raw materials:
    将N-氧-3-甲基吡啶原料投入产品合成系统内部，同时投入催化剂至产品合成系统内部；The N-oxygen-3-picoline raw material is put into the product synthesis system, and the catalyst is put into the product synthesis system at the same time;
    S2：氯化反应：S2: Chlorination Reaction:
    向上述产品合成系统内继续投入苯甲酰氯，经过氯化反应产生2-氯-5-甲基吡啶；Continue to drop into benzoyl chloride in above-mentioned product synthesis system, produce 2-chloro-5-picoline through chlorination reaction;
    S3：向上述所得的2-氯-5-甲基吡啶产品中投入引发剂、充足的催化剂，并控制引发反应得到初品2-氯-5-三氯甲基吡啶；S3: drop into initiator, sufficient catalyzer in the 2-chloro-5-methylpyridine product of above-mentioned gained, and control the initiation reaction to obtain first product 2-chloro-5-trichloromethylpyridine;
    S4：通过对上述所得物进行精馏并提纯后得到精品2-氯-5-三氯甲基吡啶；S4: obtain fine 2-chloro-5-trichloromethyl pyridine by rectifying and purifying the above-mentioned gained;
    S5：二次分离提纯2-氯-5-三氯甲基吡啶待用S5: secondary separation and purification of 2-chloro-5-trichloromethylpyridine for use
    S6：氟化反应：S6: Fluorination Reaction:
    将上述二次分离提纯后的2-氯-5-三氯甲基吡啶、五氟化碘、促进剂投入至合成系统内进行氟化反应，得含有2-氯-5-三氟甲基吡啶的粗品溶液；The 2-chloro-5-trichloromethylpyridine, iodine pentafluoride and accelerator after the above-mentioned secondary separation and purification are put into the synthesis system to carry out fluorination reaction, so as to obtain the 2-chloro-5-trifluoromethylpyridine containing 2-chloro-5-trifluoromethylpyridine the crude solution;
    S7：将粗品溶液转入产品合成系统内部的下游工序进行纯化，得到精品2-氯-5-三氟甲基吡啶。S7: The crude product solution is transferred to the downstream process inside the product synthesis system for purification to obtain the fine 2-chloro-5-trifluoromethylpyridine.
  2. 根据权利要求1所述的一种2-氯-5-三氟甲基吡啶合成方法，其特征在于：所述S3中的催化剂作为相转移催化剂使用，所述S4中的催化剂为十六烷基三甲基溴化铵或四丁基溴化铵中的一种。The method for synthesizing 2-chloro-5-trifluoromethylpyridine according to claim 1, wherein the catalyst in the S3 is used as a phase transfer catalyst, and the catalyst in the S4 is hexadecyl One of trimethylammonium bromide or tetrabutylammonium bromide.
  3. 根据权利要求1所述的一种2-氯-5-三氟甲基吡啶合成方法，其特征在于：所述氟化反应的反应温度为-20～-10℃、反应时间为36-48h。The method for synthesizing 2-chloro-5-trifluoromethylpyridine according to claim 1, wherein the reaction temperature of the fluorination reaction is -20 to -10°C, and the reaction time is 36-48 h.
  4. 根据权利要求1所述的一种2-氯-5-三氟甲基吡啶合成方法，其特征在于：所述S3步骤中的引发剂采用过氧化环己酮。The method for synthesizing 2-chloro-5-trifluoromethylpyridine according to claim 1, wherein the initiator in the step S3 adopts cyclohexanone peroxide.
  5. 根据权利要求1所述的一种2-氯-5-三氟甲基吡啶合成方法，其特征在于：所述S1步骤中的催化剂为五氧化二锑或三氧化二铝。The method for synthesizing 2-chloro-5-trifluoromethylpyridine according to claim 1, wherein the catalyst in the step S1 is antimony pentoxide or aluminum oxide.
  6. 根据权利要求1所述的一种2-氯-5-三氟甲基吡啶合成方法，其特征在于：所述S6步骤中的2-氯-5-三氯甲基吡啶、五氟化碘的重量比为5-10：1。A kind of 2-chloro-5-trifluoromethylpyridine synthesis method according to claim 1, is characterized in that: the 2-chloro-5-trichloromethylpyridine in described S6 step, the iodine pentafluoride The weight ratio is 5-10:1.
  7. 一种2-氯-5-三氟甲基吡啶合成系统，所述2-氯-5-三氟甲基吡啶合成系统为权利要求1-6中任意一项所述的产品合成系统，其特征在于：包括一密封设置的氯化反应釜组件，在所述氯化反应釜组件，在所述氯化反应釜组件的下游连接有一氟化反应釜组件，在所述氯化反应釜组件与所述氯化反应釜组件之间设有一提纯处理组件，在所述氯化反应釜组件、所述氟化反应釜组件的顶部分别设置有一氯化进料处理机构、氟化进料处理机构，所述氯化进料处理 机构用于实现将物料粒径处理合格后并输送至氯化反应釜组件内部，所述氟化进料处理机构用于实现将物料粒径处理合格后并输送至所述氟化反应釜组件内部，在所述氟化反应釜组件的出料口设置有一产品纯化组件。A 2-chloro-5-trifluoromethylpyridine synthesis system, the 2-chloro-5-trifluoromethylpyridine synthesis system is the product synthesis system described in any one of claims 1-6, wherein It includes a sealed chlorination reactor assembly, a fluorination reactor assembly is connected downstream of the chlorination reactor assembly, and the chlorination reactor assembly is connected to the chlorination reactor assembly. A purification treatment assembly is arranged between the chlorination reaction kettle components, and a chlorination feed treatment mechanism and a fluorination feed treatment mechanism are respectively provided on the top of the chlorination reaction kettle assembly and the fluorination reaction kettle assembly. The chlorinated feed processing mechanism is used to achieve qualified particle size treatment and transport it to the inside of the chlorination reactor assembly, and the fluorinated feed processing mechanism is used to achieve qualified material particle size treatment and transport it to the Inside the fluorination reaction kettle assembly, a product purification assembly is arranged at the discharge port of the fluorination reaction kettle assembly.
  8. 根据权利要求7所述的一种2-氯-5-三氟甲基吡啶合成系统，其特征在于：所述氯化反应釜组件包括一密封设置的氯化反应釜体，在所述氯化反应釜体的顶部设置有第一压力表、第一温控器、第一检修口、氯化进料口，所述氯化进料口的顶部与所述氯化进料处理机构的输出端相连接，所述氯化反应釜体的出料口与所述提纯处理组件的进口相连。A 2-chloro-5-trifluoromethylpyridine synthesis system according to claim 7, characterized in that: the chlorination reactor assembly comprises a sealed chlorination reactor body, and the chlorination reactor assembly comprises a sealed chlorination reactor body. The top of the reactor body is provided with a first pressure gauge, a first temperature controller, a first inspection port, and a chlorination feed port, and the top of the chlorination feed port and the output end of the chlorination feed treatment mechanism connected, the discharge port of the chlorination reaction kettle body is connected with the inlet of the purification treatment component.
  9. 根据权利要求8所述的一种2-氯-5-三氟甲基吡啶合成系统，其特征在于：所述氟化反应釜组件包括一密封设置的氟化反应釜体，在所述氟化反应釜体的顶部设置有第二压力表、第二温控器、第二检修口、第一氟化进料口、第二氟化进料口，所述第一氟化进料口的顶部与所述氟化进料处理机构的出料口相连接，所述第二氟化进料口与所述提纯处理组件的出口相连，所述氟化反应釜体的出口与所述产品纯化组件的进口相连。A 2-chloro-5-trifluoromethylpyridine synthesis system according to claim 8, wherein the fluorination reaction kettle assembly comprises a sealed fluorination reaction kettle body, and the fluorination reaction kettle body is arranged in a sealed manner. The top of the reactor body is provided with a second pressure gauge, a second temperature controller, a second inspection port, a first fluorination feed port, and a second fluorination feed port. The top of the first fluorination feed port It is connected with the discharge port of the fluorination feed treatment mechanism, the second fluorination feed port is connected with the outlet of the purification treatment assembly, and the outlet of the fluorination reaction kettle body is connected with the product purification assembly The import is connected.
  10. 根据权利要求9所述的一种2-氯-5-三氟甲基吡啶合成系统，其特征在于：所述提纯处理组件包括一与所述氯化反应釜体的出口相连接并用于接收来自氯化反应釜体输出的初品2-氯-5-三氯甲基吡啶的蒸馏釜，在所述蒸馏釜的下游连接有一次提纯设备，在所述一次提纯设备的下游连接有二次提纯设备，所述二次提纯设备的出口与所述氟化反应釜体的第二氟化进料口相连。A 2-chloro-5-trifluoromethylpyridine synthesis system according to claim 9, characterized in that: the purification processing component comprises a port connected to the outlet of the chlorination reaction kettle and used for receiving The distillation still of the primary product 2-chloro-5-trichloromethylpyridine output from the chlorination reactor body is connected with a primary purification device downstream of the distillation still, and a secondary purification device is connected downstream of the primary purification device equipment, the outlet of the secondary purification equipment is connected with the second fluorination feed port of the fluorination reaction kettle body.
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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0370317A1 (en) * 1988-11-22 1990-05-30 Bayer Ag Process for the preparation of substituted 2-chloropyridines
EP0438691A1 (en) * 1990-01-18 1991-07-31 Bayer Ag Process for the preparation of substituted 2-chloropyridines
CN1040431C (en) * 1992-02-19 1998-10-28 拜尔公司 Process for the preparation of 2-chloro-5-methyl-pyridine
CN102452976A (en) * 2010-10-28 2012-05-16 宁波大学 Synthetic method of 2-chloro-5-trifluoromethylpyridine
CN103787960A (en) * 2014-02-27 2014-05-14 江苏省激素研究所股份有限公司 Synthetic method of 2-chloro-5-trichloromethyl pyridine
CN206008699U (en) * 2016-08-05 2017-03-15 南通新邦化工科技有限公司 A kind of zinc stearate process units
CN111004172A (en) * 2019-12-23 2020-04-14 内蒙古元正精细化工有限责任公司 Preparation method and synthesis device of 2-chloro-3-trifluoromethylpyridine

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103288718B (en) * 2013-06-26 2015-07-15 辽宁天予化工有限公司 Preparation method of 2-chloro-5-tirfluoromethylpyridine

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0370317A1 (en) * 1988-11-22 1990-05-30 Bayer Ag Process for the preparation of substituted 2-chloropyridines
EP0438691A1 (en) * 1990-01-18 1991-07-31 Bayer Ag Process for the preparation of substituted 2-chloropyridines
CN1040431C (en) * 1992-02-19 1998-10-28 拜尔公司 Process for the preparation of 2-chloro-5-methyl-pyridine
CN102452976A (en) * 2010-10-28 2012-05-16 宁波大学 Synthetic method of 2-chloro-5-trifluoromethylpyridine
CN103787960A (en) * 2014-02-27 2014-05-14 江苏省激素研究所股份有限公司 Synthetic method of 2-chloro-5-trichloromethyl pyridine
CN206008699U (en) * 2016-08-05 2017-03-15 南通新邦化工科技有限公司 A kind of zinc stearate process units
CN111004172A (en) * 2019-12-23 2020-04-14 内蒙古元正精细化工有限责任公司 Preparation method and synthesis device of 2-chloro-3-trifluoromethylpyridine

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
WANG SHUANGMI: "Synthesis of 2-chloro-5-trifluromethylpyridine", CHINA MASTER’S THESES FULL-TEXT DATABASE, ENGINEERING SCIENCE & TECHNOLOGY I, 15 February 2012 (2012-02-15), XP055929579 *

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