CN107029636B - Production method and device of 3-ethylthio butyraldehyde - Google Patents
Production method and device of 3-ethylthio butyraldehyde Download PDFInfo
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- CN107029636B CN107029636B CN201710380775.XA CN201710380775A CN107029636B CN 107029636 B CN107029636 B CN 107029636B CN 201710380775 A CN201710380775 A CN 201710380775A CN 107029636 B CN107029636 B CN 107029636B
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- B01J3/00—Processes of utilising sub-atmospheric or super-atmospheric pressure to effect chemical or physical change of matter; Apparatus therefor
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- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
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Abstract
The application discloses a production method and a device of 3-ethylthio butyraldehyde, wherein crotonaldehyde, ethanethiol and a catalyst with the molar ratio of 0.9-1.1:1:0.01-0.03 are pumped into a coil reactor through a metering pump, and the temperature is maintained to be 20-200 ℃ and the pressure is maintained to be 5-50 kg/m 2 The time is 5-25 minutes, and then the product can be conveyed to a finished product storage tank after cooling, so as to obtain a finished product. According to the application, raw materials are introduced into a closed pipeline reactor, volatilization of ethanethiol smell is reduced through the use of a pressurizing reaction, and the post-treatment difficulty is reduced; the method has the advantages of simple reaction process, short reaction time, good tightness, better safety, high product content and stable yield.
Description
Technical Field
The application relates to the technical field of chemical production, in particular to a method and a device for producing 3-ethylsulfanyl butyraldehyde.
Background
3-ethylthiobutyraldehyde is an essential intermediate for the cyclohexenone herbicides clethodim and sethoxydim. The cyclohexenone herbicide has high selectivity, can prevent and treat various grassy weeds, including annual grassy weeds and perennial grassy weeds, is safe to dicotyledonous crops, and is a high-efficiency, low-toxicity and low-residue herbicide.
At present, the main process for synthesizing the 3-ethylthio butyraldehyde comprises the following steps:
U.S. patent No. 4440566 and the Chinese literature on the progress of synthesis research of clethodim, describe that 3-ethylthiobutyraldehyde is synthesized by taking crotonaldehyde and ethanethiol as raw materials, and the ethanethiol and the crotonaldehyde react in a kettle reactor under the action of a catalyst through stirring at 30 ℃ to generate 3-ethylthiobutyraldehyde, then the 3-ethylthiobutyraldehyde and dimethyl malonate are condensed into a ring, and then alkaline hydrolysis and acidification decarboxylation are carried out to obtain the target product trione (formula a). The production method of the process route is lag, the production condition is poor, the reaction heat release amount is large, the dripping reaction is needed, the heat is wasted, the production time is long, and the intermittent reaction is long, and because the ethanethiol with strong and lasting odor is needed to be used as the raw material, the whole production process needs to consider the ethanethiol gas treatment, and the tail gas treatment difficulty is increased.
In terms of production equipment, the operation of preparing 3-ethylthiobutyraldehyde by using a traditional kettle-type reactor is commonly used at present, and because the traditional kettle-type reactor is used, in order to better remove the problem of reaction heat, a coil pipe is used for cooling, and a method of dropwise adding ethanethiol is adopted to prevent the concentrated heat release of the reaction. Besides the kettle type reactor, facilities such as a high-level tank, a dripping tank and the like are also required, and a jacket in the kettle type reactor needs to be subjected to operations such as heat preservation, temperature reduction and the like. The whole set of equipment occupies large space, has poor sealing performance and low production efficiency.
Disclosure of Invention
The technical problems to be solved by the application are as follows:
the method for producing the 3-ethylthio butyraldehyde is provided, raw materials are introduced into a closed pipeline reactor, volatilization of the smell of the ethanethiol is reduced through the use of a pressurizing reaction, and the difficulty of post-treatment is reduced; the method has the advantages of simple reaction process, short reaction time, good tightness, better safety, high product content and stable yield.
The production device of the 3-ethylthio butyraldehyde is simple, good in tightness, better in safety, small in occupied area, high in product quality and stable in yield.
In order to solve the technical problems, the technical scheme of the application is as follows:
a method for producing 3-ethylthio butyraldehyde, comprising the following steps:
a. pumping crotonaldehyde, ethanethiol and catalyst with a molar ratio of 0.9-1.1:1:0.01-0.03 into a coil reactor through a metering pump;
b. fully mixing the materials conveyed to the coil reactor in the step a, and maintaining the temperature to be 20-200 ℃ and the pressure to be 5-50 kg/m 2 The time is 5-25 minutes;
c. c, conveying the product obtained in the step b to a condenser for condensation for 10-60 minutes, and cooling to 20-30 ℃;
d. and c, conveying the product obtained in the step c to a finished product storage tank to obtain a finished product.
Preferably, the molar ratio of crotonaldehyde, ethanethiol and catalyst in step a is 1:1:0.02.
Preferably, the catalyst of step a comprises triethylamine, pyridine and n-butylamine.
Preferably, the catalyst in step a is triethylamine.
Preferably, the temperature in step b is 120℃and the pressure is 20kg/m 2 The time was 10 minutes.
Preferably, the condensation time in step c is 30 minutes.
A production device of 3-ethylthio butyraldehyde comprises a coil pipe reactor, a condenser and a finished product storage tank which are sequentially communicated; the device also comprises an ethanethiol storage tank, a crotonaldehyde storage tank, a catalyst storage tank and corresponding ethanethiol metering pumps, crotonaldehyde metering pumps and catalyst metering pumps; the ethyl mercaptan storage tank, the crotonaldehyde storage tank and the catalyst storage tank are respectively communicated with the material inlet of the coil reactor through an ethyl mercaptan metering pump, a crotonaldehyde metering pump and a catalyst metering pump, the material outlet of the coil reactor is communicated with the material inlet of the condenser, and the material outlet of the condenser is communicated with the material inlet of the finished product storage tank.
Preferably, the coil reactor comprises: the coil pipe reactor comprises a coil pipe reactor main body, wherein a cavity is formed in the main body, a heat conducting oil outlet and a material outlet are formed in the upper part of the main body, and a heat conducting oil inlet and a material inlet are formed in the lower part of the main body; a coil is arranged on the inner wall of the main body, and two ends of the coil are respectively communicated with a material inlet and a material outlet; the coil pipe is also provided with a plurality of mixing units and a plurality of flow guiding devices, and the material outlet is provided with a back pressure valve. The back pressure valve can adjust the reaction pressure in the coil reactor.
The inner wall of the coil pipe reactor is provided with a coil pipe manufactured by stainless steel seamless pipes, the inside of the coil pipe is used for conveying and reacting materials, the outside of the coil pipe is used for keeping the reaction temperature through heat conduction oil, and a mixing unit of 1 meter is matched with each 20 meters in the coil pipe, so that mass transfer is enhanced, and the reaction is more facilitated. A flow guiding device is arranged in the coil pipe at intervals of 5 meters, so that materials which flow slowly at the pipe wall can be guided into the radial middle part of the pipe, and the fluid mixing speed is improved.
Preferably, the mixing unit is an SK mixing unit, an SV mixing unit or an SL static mixer; most preferably an SK hybrid unit.
Preferably, the flow guiding device is a hollow conical round table which is arranged in the coil pipe.
Preferably, the condenser is a tube array heat exchanger.
Due to the adoption of the technical scheme, the application has the beneficial effects that:
1. the production reaction is carried out in a closed pipeline, certain reaction pressure is maintained, the problem of vaporization of ethanethiol is avoided, and the metering pump is used for continuously metering and feeding, so that the problem of leakage of ethanethiol during batch feeding of intermittent reaction is avoided, and the operation environment can be improved;
2. the production reaction of the method effectively solves the heat transfer problem and accelerates the reaction process: the operation of preparing 3-ethylthio butyraldehyde by using the traditional kettle type reactor has to adopt a coil pipe for cooling in order to better remove the problem of reaction heat, and adopts a method of dripping ethanethiol to prevent the concentrated heat release of the reaction; the production equipment of the method can fundamentally solve the heat exchange problem of reactants due to the large specific surface area, the two components are fed according to the proportion, the reaction concentration is high, and the reaction is completed instantaneously;
3. the production process of the method realizes material saving: the ratio of the reactants is 1:1 mole as can be seen by the equation, but the batch reaction is carried out with the molar ratio of about 1.05:1 in order to increase the yield and ensure smooth production, and crotonaldehyde is excessively added; the method can effectively reduce the proportion of the reaction, and basically adds reactants in an equimolar ratio of 1:1;
4. the production process of the method can realize the improvement of the reaction temperature and effectively improve the reaction speed: because the reaction coefficient is related to the temperature and the catalyst, the reaction speed can be increased by 2-4 times when the temperature is increased by 10 ℃, and because the pressurizing reaction can be arranged in the equipment in the production process of the method, the vaporization problem of ethanethiol is effectively avoided, and the reaction temperature can be increased to 20-200 ℃, so that the reaction speed is effectively increased;
5. the production process of the method can realize the reduction of the volume of reaction equipment and the increase of production safety: in the prior art, an intermittent kettle type reactor is used for producing 4 batches of materials every day, the feeding time of each batch of materials is 2 hours, the dripping time is 2 hours, the reaction time is 4-5 hours, the discharging time is 1 hour, the total time is 10-12 hours, 2 batches of materials are fed to each device every day, 2 reaction devices are needed, the volume of each device is about 1.5 cubes, 1 cube is filled with the materials, the whole volume of the materials is 4 cubes, the total volume of 2 sets of devices is about 3000 liters, the floor area of a platform frame is 50 square meters, and the height is 3.5 meters; a high-level tank, a dripping tank, a jacket and the like are also needed, and operations such as heat preservation, temperature reduction and the like are also needed; the coil reactor used in the method also produces 4 cubes of material per day, 167 liters per hour, 3 liters per minute, and 0.05 liters per second. The reaction time was 10 minutes, the volume of the apparatus was only 30 liters, the floor area was 20 square meters and the height was 4 meters.
Therefore, the method introduces the raw materials into a closed pipeline reactor, reduces volatilization of the smell of the ethanethiol through the use of a pressurizing reaction, and reduces the difficulty of post-treatment; the method has the advantages of simple reaction process, short reaction time, good tightness, better safety, high product content and stable yield.
Drawings
The application will be further described with reference to the drawings and examples.
FIG. 1 is a schematic view of the construction of the production apparatus of the present application;
FIG. 2 is a schematic illustration of the structure of a deflector in a coil reactor according to the present application;
wherein, 1-ethanethiol storage tank; a 2-crotonaldehyde storage tank; 3-a catalyst storage tank; a 4-ethanethiol metering pump; a 5-crotonaldehyde metering pump; 6-a catalyst metering pump; 7-coil reactor; 8-a conduction oil inlet; 9-a heat conducting oil outlet; 10-coil pipe; 11-material inlet; 12-material outlet; 13-a condenser; 14-a finished product storage tank; 15-a back pressure valve; 16-a flow guiding device.
Detailed Description
The application is further illustrated in the following, in conjunction with the accompanying drawings and examples.
Example 1Production facility related to the production of the application
As shown in fig. 1 and 2, the production equipment of 3-ethylthiobutyraldehyde comprises an ethanethiol storage tank 1, a crotonaldehyde storage tank 2 and a catalyst storage tank 3; the equipment respectively conveys materials to a coil reactor 7 for reaction through an ethanethiol metering pump 4, a crotonaldehyde metering pump 5 and a catalyst metering pump 6; heating by heat conduction oil in the reaction process, wherein the heat conduction oil enters through a heat conduction oil inlet 8 at the bottom of the coil reactor 7; is led out through a heat conducting oil outlet 9 at the bottom of the coil reactor 7; the heat conducting oil is used for heating materials in the coil pipe 10, the materials enter from a material inlet 11 positioned at the bottom of the coil pipe reactor 7, and are output from a material outlet 12 positioned at the upper part of the coil pipe reactor 7 after reaction; after being condensed by the condenser 13, the waste water can be conveyed to a finished product storage tank 14 for storage; in addition, a deflector 16 and a mixing unit are also provided within the coil 10. A back pressure valve 15 is also arranged at the material outlet 12 of the coil reactor 7.
Example two
Crotonaldehyde is fed into a coil reactor 7 through a crotonaldehyde metering pump 5 at a flow rate of 87.5 kg/h, triethylamine is fed into a catalyst metering pump 6 at a flow rate of 2.5 kg/h, ethanethiol is fed into an ethanethiol metering pump 4 at a flow rate of 77.7 kg/h, the reaction temperature is kept at 30 ℃, the residence time in the coil reactor 7 is 25 minutes, the reaction pressure of the materials is controlled to be 20kg through a back pressure valve 15 on a material outlet 12, and the reacted materials enter a finished product storage tank 14 through a pipeline. The content of the finished product reaches 94 percent, and the finished product is directly used for the next reaction. The reaction temperature is controlled at 30 ℃, so that the reaction speed is low, the reaction is incomplete, and the condensation through the condenser 13 is not needed.
Example III
Crotonaldehyde is fed into a coil reactor 7 through a crotonaldehyde metering pump 5 at a flow rate of 87.5 kg/h, triethylamine is fed into a catalyst metering pump 6 at a flow rate of 2.5 kg/h, ethanethiol is fed into an ethanethiol metering pump 4 at a flow rate of 77.7 kg/h, the reaction temperature is kept at 50 ℃, the residence time in the coil reactor 7 is 20 minutes, the reaction pressure of the materials is controlled to be 20kg through a back pressure valve 15 on a material outlet 12, and the reacted materials are condensed to 30 ℃ through a condenser 13 and then enter a finished product storage tank 14. The content of the finished product reaches 95.4 percent, and the finished product is directly used for the next reaction.
Example IV
Crotonaldehyde is fed into a coil reactor 7 through a crotonaldehyde metering pump 5 at a flow rate of 87.5 kg/h, triethylamine is fed into a catalyst metering pump 6 at a flow rate of 2.5 kg/h, ethanethiol is fed into an ethanethiol metering pump 4 at a flow rate of 77.7 kg/h, the reaction temperature is kept at 80 ℃, the residence time in the coil reactor 7 is 15 minutes, the reaction pressure of the materials is controlled to be 20kg through a back pressure valve 15 on a material outlet 12, and the reacted materials are condensed to 30 ℃ through a condenser 13 and then enter a finished product storage tank 14. The content of the finished product reaches 98.5 percent, and the finished product is directly used for the next reaction.
Example five
Crotonaldehyde is fed into a coil reactor 7 through a crotonaldehyde metering pump 5 at a flow rate of 87.5 kg/h, triethylamine is fed into a catalyst metering pump 6 at a flow rate of 2.5 kg/h, ethanethiol is fed into an ethanethiol metering pump 4 at a flow rate of 77.7 kg/h, the reaction temperature is kept at 120 ℃, the residence time in the coil reactor 7 is 10 minutes, the reaction pressure of the materials is controlled to be 20kg through a back pressure valve 15 on a material outlet 12, and the reacted materials are condensed to 30 ℃ through a condenser 13 and then enter a finished product storage tank 14. The content of the finished product reaches 99 percent and is directly used for the next reaction.
Example six
Crotonaldehyde is fed into a coil reactor 7 through a crotonaldehyde metering pump 5 at a flow rate of 175 kg/h, triethylamine is fed into a catalyst metering pump 6 at a flow rate of 5 kg/h, ethanethiol is fed into an ethanethiol metering pump 4 at a flow rate of 155.4 kg/h, the reaction temperature is kept at 150 ℃, the residence time in the coil reactor 7 is 5 minutes, the reaction pressure of the materials is controlled to be 50kg through a back pressure valve 15 on a material outlet 12, and the reacted materials are condensed to 30 ℃ through a condenser 13 and then fed into a finished product storage tank 14. The content of the finished product reaches 99 percent and is directly used for the next reaction.
Example sevenControl: production conditions of the prior art
Proportioning: crotonaldehyde: ethanethiol: triethylamine = 1:1.03:0.02
525 kg (7.5 mol) of crotonaldehyde is metered by a high-level tank and is put into a reaction kettle with 1.5 cubic meters, 15 kg (0.15 mol) of triethylamine is accurately added into the reaction kettle by a triethylamine metering tank to serve as a catalyst, chilled water in a coil pipe is started to be cooled to 25 ℃, and 480 kg (7.73 mol) of ethanethiol is metered and dropwise added. The temperature is controlled not to exceed 30 ℃ in the dripping process, and the dripping is completed within 4 hours. Keeping the temperature at 30 ℃ for 4-5 hours, strictly controlling the temperature in the heat preservation process, and carrying out the next reaction without separation, wherein the total material after the reaction is 1020 kg and the content is about 97%.
It is to be understood that these examples are illustrative of the present application and are not intended to limit the scope of the present application. Furthermore, it should be understood that various changes and modifications can be made by one skilled in the art after reading the teachings of the present application, and such equivalents are intended to fall within the scope of the application as defined in the appended claims.
Claims (8)
1. The production method of the 3-ethylthio butyraldehyde is characterized by comprising the following steps:
a. pumping crotonaldehyde, ethanethiol and catalyst with a molar ratio of 0.9-1.1:1:0.01-0.03 into a coil reactor through a metering pump;
b. fully mixing the materials conveyed to the coil reactor in the step a, and maintaining the temperature to be 20-200 ℃ and the pressure to be 5-50 kg/m 2 The time is 5-25 minutes;
c. c, conveying the product obtained in the step b to a condenser for condensation for 10-60 minutes, and cooling to 20-30 ℃;
d. c, conveying the product obtained in the step c to a finished product storage tank to obtain a finished product;
the coil reactor comprises: the coil pipe reactor comprises a coil pipe reactor main body, wherein a cavity is formed in the main body, a heat conducting oil outlet and a material outlet are formed in the upper part of the main body, and a heat conducting oil inlet and a material inlet are formed in the lower part of the main body; a coil is arranged on the inner wall of the main body, and two ends of the coil are respectively communicated with a material inlet and a material outlet; the coil pipe is also provided with a plurality of mixing units and a plurality of flow guiding devices, and the material outlet is provided with a back pressure valve.
2. The method for producing 3-ethylsulfanyl butyraldehyde as recited in claim 1, wherein: the mol ratio of crotonaldehyde, ethanethiol and catalyst in the step a is 1:1:0.02.
3. The method for producing 3-ethylsulfanyl butyraldehyde as recited in claim 1, wherein: the catalyst in the step a comprises triethylamine, pyridine and n-butylamine.
4. The method for producing 3-ethylsulfanyl butyraldehyde as recited in claim 1, wherein: the catalyst in the step a is triethylamine.
5. The method for producing 3-ethylsulfanyl butyraldehyde as recited in claim 1, wherein: the temperature in the step b is 120 ℃ and the pressure is 20kg/m 2 The time was 10 minutes.
6. The method for producing 3-ethylsulfanyl butyraldehyde as recited in claim 1, wherein: the mixing unit is an SK mixing unit, an SV mixing unit or an SL static mixer.
7. The method for producing 3-ethylsulfanyl butyraldehyde as recited in claim 1, wherein: the flow guiding device is a hollow conical round table which is arranged in the coil pipe.
8. The method for producing 3-ethylsulfanyl butyraldehyde as recited in claim 1, wherein: the condenser is a tube array heat exchanger.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003213343A (en) * | 2002-01-22 | 2003-07-30 | Daido Steel Co Ltd | Vacuum evaporation and recovery apparatus |
| CN105418470A (en) * | 2015-11-17 | 2016-03-23 | 江苏长青农化股份有限公司 | Synthetic method of clethodim |
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- 2017-05-25 CN CN201710380775.XA patent/CN107029636B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003213343A (en) * | 2002-01-22 | 2003-07-30 | Daido Steel Co Ltd | Vacuum evaporation and recovery apparatus |
| CN105418470A (en) * | 2015-11-17 | 2016-03-23 | 江苏长青农化股份有限公司 | Synthetic method of clethodim |
Non-Patent Citations (1)
| Title |
|---|
| 戴立言 ; 方俊 ; 姜昕鹏 ; 石永根 ; 陈英奇 ; 吕秀阳 ; .5-[2-(乙硫基)丙基]-1,3-环己二酮的合成工艺研究.高校化学工程学报.2006,(06),第974-976页. * |
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