CN111205201B - Method and system for producing N-cyanoethyl-N-benzylaniline - Google Patents
Method and system for producing N-cyanoethyl-N-benzylaniline Download PDFInfo
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Abstract
The invention provides a method and a system for producing N-cyanoethyl-N-benzylaniline, which firstly use the hypergravity to carry out cyanoethylation and benzylation reactions, greatly strengthen mass transfer effects and micromixing, improve reaction conversion rate to a great extent, shorten reaction time, and simultaneously continuously measure feeding and discharging in the reaction process.
Description
Technical Field
The invention belongs to the field of dye intermediate preparation, and particularly relates to a method and a system for producing N-cyanoethyl-N-benzylaniline.
Background
N-cyanoethyl-N-benzylaniline is an important fine chemical raw material and intermediate, and is widely applied to synthesis of pesticides and dyes. In industry, production is carried out in a stirred tank reactor in a batch operation mode, and due to the complexity of organic reaction and the large volume of the stirred tank reactor, the temperature of materials and the mixing effect are difficult to achieve uniformity in local areas, the mass transfer effect is poor, and the production efficiency is low.
At present, the domestic production adopts a batch kettle method, water, acrylonitrile, zinc chloride, glacial acetic acid and aniline are heated and refluxed in a reaction kettle, and after the reaction is finished, distilling to recover acrylonitrile, cooling and crystallizing the distillation mother liquor, filtering and washing to obtain N-cyanoethylaniline, then heating up N-cyanoethylaniline, water, soda ash and benzyl chloride in a reaction kettle for reflux reaction, filtering and washing after the reaction is finished to obtain the N-cyanoethylaniline, wherein the process product needs operations such as distillation, layering, neutralization and the like, the operation is complex, the operation steps are multiple, the energy consumption is large, the content of the N, N-dicyanoethylaniline in the produced N-cyanoethylaniline is high, the method has influence on the quality of subsequent production varieties, and meanwhile, the comprehensive yield of the two-step reaction is about 85 percent, the wastewater amount is large, the energy consumption is high, and the reflux reaction time is long.
In view of the problems of the batch tank process, patent application publication No. CN 109503424a discloses an apparatus and a method for producing N-cyanoethyl-N-benzylaniline, comprising: adding aniline, acrylonitrile, zinc chloride and glacial acetic acid into a primary reaction kettle, and performing heating reflux reaction to obtain an N-cyanoethyl benzyl chloride solution; and then conveying the N-cyanoethyl benzyl chloride solution into a second reaction kettle, adding sodium bicarbonate and benzyl chloride, heating and carrying out reflux reaction to obtain the N-cyanoethyl-N-benzyl aniline, wherein the two-step comprehensive yield is higher than 96%. The method has long reaction time, takes reactants as a solvent, and also needs to recover the solvent, so the method has complicated production steps and is not suitable for industrial large-scale production.
The supergravity technology is a new technology for strengthening mass transfer, mixing and chemical reaction, and utilizes the centrifugal force generated by the rotation of the rotor in the supergravity rotating bed to simulate the supergravity environment to strengthen the transfer and reaction processes, thereby greatly improving the efficiency of the mass transfer and reaction processes. The supergravity rotating bed device mainly includes closed shell body, in the interior of said shell body a rotating rotor is set, on the rotor an annular packing layer is set, and different fluids can be flowed into the rotating bed from correspondent inlet of shell body, and the mass transfer process can be implemented under the centrifugal force field in the rotating packing layer, and its mass transfer rate can be raised by 1-3 order of magnitude compared with that of traditional reactors.
In a word, finding a synthesis process which can realize continuous production, strengthen mass transfer and mixing, greatly shorten reaction time and simultaneously recycle mother liquor water and washing water becomes a hot point of current research.
Disclosure of Invention
The invention aims to provide a method and a system for producing N-cyanoethyl-N-benzylaniline, which not only greatly improve the reaction efficiency and shorten the reaction time, but also ensure the high-purity and high-yield output of the product, have extremely strong economic benefit and are very suitable for industrial production.
The invention provides a method for producing N-cyanoethyl-N-benzylaniline, which comprises the following steps:
cyanoethylation reaction: continuously pumping aniline, acrylonitrile and mother liquor water A into a first supergravity reactor for mixing reaction, allowing the obtained reaction mixture A to flow into a first circulating tank, allowing the first circulating tank and the first supergravity reactor to form a first circulating system, discharging after circulating reaction, and performing oil-water separation to obtain N-cyanoethylaniline; the mother liquor A is obtained by mixing a water phase separated from the oil and water with a catalyst and a polymerization inhibitor;
benzylation reaction: continuously pumping the N-cyanoethylaniline, benzyl chloride and mother liquor water B into a second supergravity reactor for mixing reaction, allowing the reaction mixture B to flow into a second circulating tank and enabling the second circulating tank and the second supergravity reactor to form a second circulating system, continuously discharging to a dilution kettle after circulating reaction, cooling, separating materials, centrifuging and washing to obtain the N-cyanoethyl-N-benzylaniline; and the mother liquor water B is obtained by mixing the water phase obtained by centrifugation with an acid-binding agent.
In the cyanoethylation reaction, the molar ratio of aniline to acrylonitrile is 1:1-1.5, wherein the feeding amount of the mother liquor water A is 1-10 times of the mass of the aniline.
In the cyanoethylation reaction, the catalyst is a composite catalyst consisting of hydrochloric acid and zinc chloride, the mass concentration of the hydrochloric acid is 30-35 wt%, and the mass ratio of the hydrochloric acid to the zinc chloride is 1-3: 1.
in the cyanoethylation reaction, the polymerization inhibitor is hydroquinone; the dosage of the polymerization inhibitor is 0.1-5% of the mass of the acrylonitrile.
In the benzylation reaction, the molar ratio of the N-cyanoethylaniline to the benzyl chloride is 1:1-1.5, and the feeding amount of the mother liquor water B is 1-10 times of the mass of the N-cyanoethylaniline.
In the benzylation reaction, an acid-binding agent is added to adjust the pH value of the benzylation reaction system to 3-11, and the pH value is preferably 6-8. The acid-binding agent is selected from one or more of ammonia water, sodium carbonate and sodium bicarbonate.
The hypergravity reactor comprises a hypergravity rotating packed bed, a hypergravity rotating deflecting fluidized bed, a hypergravity rotating spiral channel, a hypergravity rotating disc or a stator-rotor hypergravity rotating device.
Preferably, the hypergravity reactor is a hypergravity rotating packed bed, and the hypergravity action of the rotating packed bed promotes reaction materials to flow and contact in a porous medium, so that huge shearing force is generated to tear liquid into a nanoscale liquid film, liquid threads or liquid drops, and the internal micromixing and reaction mass transfer effects are enhanced. Further preferably, the rotating speed of the super-gravity rotating packed bed is 500-.
The invention also discloses a system for producing the N-cyanoethyl-N-benzylaniline, which comprises the following steps: the system comprises a first hypergravity reactor, a first circulating tank, an oil-water separator, a first mother liquid tank, a second hypergravity reactor, a second circulating tank, a dilution kettle, a second mother liquid tank, a centrifugal machine and a washing tank which are connected in sequence;
the first hypergravity reactor is communicated with a first circulating tank to form circulation, the first circulating tank is communicated with an oil-water separator, a discharge hole of the oil-water separator is respectively connected to a feed hole of a first mother liquid tank and a feed hole of a second hypergravity reactor, and the discharge hole of the first mother liquid tank is connected with the feed hole of the first hypergravity reactor;
the second hypergravity reactor is communicated with a second circulating tank to form circulation, the second circulating tank is sequentially communicated with the dilution kettle and the centrifugal machine, and a discharge hole of the centrifugal machine is respectively connected to a feed inlet of a second mother liquid tank and a feed inlet of the washing tank.
Compared with the prior art, the invention has the following beneficial effects:
1. the reaction conversion rate can be improved to a great extent by applying the supergravity enhanced mass transfer effect and the micromixing, the reaction time is greatly shortened, and the production efficiency is high.
2. The invention continuously measures the feeding and discharging in the whole reaction process, can accurately control the reaction conditions such as temperature, pressure, pH value and the like required by a reaction system, obviously reduces the occurrence of side reactions and improves the product quality. The invention realizes industrial continuous production, greatly reduces workshop operators, and improves workshop production environment and safety measures.
3. The mother liquor and the washing water are recycled in the continuous production process, so that the wastewater discharge is greatly reduced, and the wastewater treatment cost is reduced.
4. In the production process of the N-cyanoethylaniline, the N-cyanoethylaniline is separated in a layered mode, material separation and washing are not needed in the middle, the operation steps and the generation of waste water are reduced, and the production efficiency is improved.
Drawings
FIG. 1 is a process flow diagram for the production of N-cyanoethyl-N-benzylaniline according to the present invention.
FIG. 2 is a diagram of a system for producing N-cyanoethyl-N-benzylaniline according to the present invention, wherein 1-a first hypergravity reactor, 2-a first circulation tank, 3-a first circulation pump, 4-a first transfer metering pump, 5-an oil-water separator, 6-a cyanoethyl mother liquor metering pump, 7-a first mother liquor tank, 8-a first mother liquor metering pump, 9-N-cyanoethyl aniline metering pump, 10-a second hypergravity reactor, 11-a second circulation tank, 12-a second circulation pump, 13-a second transfer metering pump, 14-a dilution tank, 15-N-cyanoethyl-N-benzylaniline metering pump, 16-a centrifuge, 17-a waste water tank, 18-a washing water tank, 19-a washing water metering pump, wastewater treatment, and recycling, and the like, 20-a second mother liquor metering pump and 21-a second mother liquor tank.
Detailed Description
The technical solutions in the embodiments of the present invention are clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be obtained by a person skilled in the art without any inventive step based on the embodiments of the present invention, are within the scope of the present invention.
The invention discloses a method for producing N-cyanoethyl-N-benzylaniline, which comprises the following steps:
cyanoethylation reaction: continuously pumping aniline, acrylonitrile and mother liquor water A into a first supergravity reactor for mixing reaction, allowing the obtained reaction mixture A to flow into a first circulating tank, allowing the first circulating tank and the first supergravity reactor to form a first circulating system, discharging after circulating reaction, and performing oil-water separation to obtain N-cyanoethylaniline; the mother liquor A is obtained by mixing a water phase separated from the oil and water with a catalyst and a polymerization inhibitor;
benzylation reaction: continuously pumping the N-cyanoethylaniline, benzyl chloride and mother liquor water B into a second supergravity reactor for mixing reaction, allowing the reaction mixture B to flow into a second circulating tank, allowing the second circulating tank and the second supergravity reactor to form a second circulating system, and continuously discharging the mixture after circulating reaction to a dilution kettle for cooling, separating, centrifuging and washing to obtain the N-cyanoethyl-N-benzylaniline; and the mother liquor water B is obtained by mixing the water phase obtained by centrifugation with an acid-binding agent.
In the cyanoethylation reaction, the N-cyanoethylaniline, the acrylonitrile and the mother liquor A are continuously fed according to a certain proportion, and the feeding amount of the raw materials is controlled to ensure that the reaction is complete; preferably, the molar ratio of the N-cyanoethylaniline to the acrylonitrile is 1:1-1.5, wherein the feeding amount of the mother liquor water A is 1-10 times of the mass of the N-cyanoethylaniline.
The mother liquid A is obtained by adding a catalyst and a polymerization inhibitor into the N-cyanoethylaniline mother liquid separated from the oil and water and then mixing, and then the mother liquid A is pumped into the first hypergravity device for cyclic utilization, so that resources are greatly saved, the discharge of waste water is reduced, and the production cost is reduced.
The catalyst is a catalyst commonly used in cyanoethylation reaction by a person skilled in the art, and is preferably a composite catalyst consisting of hydrochloric acid and zinc chloride, wherein the mass ratio of the hydrochloric acid to the zinc chloride is 1-3: 1. the amount of catalyst used in the present invention is not particularly limited, and the catalyst is used as is well known to those skilled in the art, and in the specific examples, the amount of catalyst is 10% to 50% by mass of aniline.
The polymerization inhibitor is preferably hydroquinone, which is soluble in water and stable in chemical property, so that acrylonitrile in the reaction system can be prevented from being polymerized. The amount of the polymerization inhibitor is determined according to the amount of acrylonitrile, and is preferably 0.1-5% of the mass of the acrylonitrile.
In the above cyanoethylation reaction, the rotor speed of the first hypergravity reactor is 500-. And the residence time of the reaction mixture A in the first circulation system is controlled to be 0.5-5h, preferably 0.5-2h, so that the reaction materials can be ensured to be completely reacted and the generation amount of byproducts is small in the preferred circulation time.
In the first hypergravity reactor, the temperature of the cyanoethylation reaction is 50-130 ℃, and the optimal temperature is 70-100 ℃; the reaction pressure is 0MPa to 1.5MPa, preferably 0.2MPa to 0.5 MPa.
In the benzylation reaction, the N-cyanoethylaniline, the benzyl chloride and the second mother liquor are continuously fed according to a certain proportion, and the reaction is completed by controlling the feeding amount of raw materials; preferably, the molar ratio of the N-cyanoethylaniline to the benzyl chloride is 1:1-1.5, and the feeding amount of the second mother liquor water is 1-10 times of the mass of the N-cyanoethylaniline.
And adding an acid-binding agent into the second mother liquor water to adjust the pH value of the second mother liquor water. The acid-binding agent of the present invention is not particularly limited in kind, and may be selected from acid-binding agents known to those skilled in the art, and in the present invention, one or more of ammonia water, sodium carbonate, and sodium bicarbonate is preferred. In the benzylation reaction, an acid-binding agent is added to adjust the pH value to 3-11, and the pH value is preferably 6-8.
In the benzylation reaction, the rotor speed of the second hypergravity reactor is 500-2800r/min, and the most preferable range is 1200-2000 r/min. And the residence time of the reaction mixture A in the second circulation system is controlled to be 0.5-5h, preferably 0.5-1h, so that the reaction materials can be ensured to be completely reacted and the generation amount of byproducts is small in the preferred circulation time.
In the second hypergravity reactor, the temperature of the benzylation reaction is 50-130 ℃, and preferably 60-110 ℃; the reaction pressure is 0MPa to 1.5MPa, preferably 0.2MPa to 0.7 MPa.
In the benzylation reaction, the centrifugally separated N-cyanoethyl-N-benzylaniline mother liquor and an acid-binding agent are mixed to regulate the pH value of the system, and then the mixed solution is pumped into a second supergravity reactor for recycling, so that the recycling of the mother liquor is realized. After being collected, the washing water is cooled and added into a dilution kettle to separate out the N-cyanoethyl-N-benzylaniline, so that the recycling of the washing water is realized.
The invention also discloses a system for producing the N-cyanoethyl-N-benzylaniline, which comprises the following steps: the system comprises a first hypergravity reactor, a first circulating tank, an oil-water separator, a first mother liquid tank, a second hypergravity reactor, a second circulating tank, a dilution kettle, a second mother liquid tank, a centrifugal machine and a washing tank which are connected in sequence;
the first hypergravity reactor is communicated with a first circulating tank to form circulation, the first circulating tank is communicated with an oil-water separator, a discharge hole of the oil-water separator is respectively connected to a feed hole of a first mother liquid tank and a feed hole of a second hypergravity reactor, and the discharge hole of the first mother liquid tank is connected with the feed hole of the first hypergravity reactor;
the second hypergravity reactor is communicated with a second circulating tank to form circulation, the second circulating tank is sequentially communicated with the dilution kettle and the centrifugal machine, and a discharge hole of the centrifugal machine is respectively connected to a feed inlet of a second mother liquid tank and a feed inlet of the washing tank.
Preferably, after the materials in the first circulation tank, the second circulation tank, the oil-water separator and the dilution kettle reach a certain liquid level, the feeding speed and the discharging speed of the system are kept consistent, and the height of the designated liquid level is kept unchanged.
Examples
An embodiment of the present invention will be described in detail with reference to fig. 1 and 2. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products commercially available.
The method in a specific embodiment comprises the following steps:
(1) continuously pumping aniline, acrylonitrile and mother liquor A into a first hypergravity reactor 1 for reaction in a certain proportion mode through a metering pump, enabling materials to flow into a first circulating tank 2, and starting a first circulating pump 3 to convey the materials to the first hypergravity reactor 1 for mixing reaction;
(2) when the first circulating tank 2 reaches a liquid level, continuously conveying the materials to an oil-water separator 5 through a first transfer metering pump 4, pumping the separated lower-layer mother liquor into a first mother liquor tank 7 through a cyanoethyl mother liquor metering pump 6, adding a catalyst and a polymerization inhibitor into the first mother liquor tank 7, and pumping the obtained mother liquor water A into a first supergravity reactor 1 through a mother liquor metering pump 8; continuously pumping the separated upper-layer material N-cyanoethylaniline into a second hypergravity reactor 10 through an N-cyanoethylaniline metering pump 9, and continuously pumping the reaction material into an oil-water separator in the process, wherein the liquid level is kept unchanged;
(3) continuously pumping N-cyanoethylaniline, benzyl chloride and mother liquor B into a second super-gravity reactor 10 for mixing in a certain proportion mode through a metering pump, enabling the materials to flow into a second circulating tank 11, and conveying the materials to the second super-gravity reactor 10 for mixing reaction by using a second circulating pump 12;
(4) when the second circulation tank 11 reaches a satisfactory liquid level, continuously conveying the material to a dilution kettle 14 through a second transfer metering pump 13, continuously adding industrial water or washing water into the dilution kettle 14 through a washing water metering pump 19 for cooling and precipitating the material, continuously pumping the material of the dilution kettle 14 into a centrifuge 16 through an N-cyanoethyl-N-benzylaniline metering pump 15 to obtain N-cyanoethyl-N-benzylaniline through centrifugation, and maintaining the liquid level height; mother liquor after centrifugation is pumped into a second mother liquor tank 21 through a waste water pump 17, an acid binding agent is added into the second mother liquor tank 21 to adjust the pH value, then the mother liquor is pumped into a second supergravity reactor 10 through a second mother liquor water metering pump 20, and washing water is pumped into a washing water tank 18 through the waste water pump 17 and is used for diluting kettle cooling thinner.
(5) The product N-cyanoethyl-N-benzylaniline is dried by a centrifuge 16, packaged and measured.
Example 1
(1) Cyanoethylation reaction:
setting a pump, respectively using 170g/min of aniline, acrylonitrile and mother liquor A, the method comprises the steps of continuously pumping 100g/min and 325g/min of materials into a first supergravity reactor for mixing reaction at 83-85 ℃, wherein the reaction pressure is 0.2MPa, the material retention time of a circulating system formed by the first supergravity reactor and a first circulating tank is 60min, the first circulating tank continuously discharges materials into an oil-water separator at the flow rate of 595g/min, standing and layering are carried out, a lower-layer mother solution of the oil-water separator is pumped into a first mother solution tank, 20 wt% of aniline mass catalyst (the mass ratio of hydrochloric acid to zinc chloride is 2: 1) and 1 wt% of acrylonitrile mass polymerization inhibitor (hydroquinone) are added into the first mother solution tank, then the materials are pumped into the first supergravity reactor, an upper-layer material N-cyanoethylaniline is continuously pumped into a second supergravity reactor, and the materials flow into the oil-water separator all the time in the process, and the liquid level is kept unchanged.
(2) Benzylation reaction:
continuously pumping N-cyanoethylaniline (with the content of 81.5%) output in the step (1), benzyl chloride and mother liquor water B (with the content of 20% soda ash) into a second super-gravity reactor at the flow rates of 325g/min, 240g/min and 500g/min respectively for mixing, wherein the reaction temperature is 95-98 ℃, the reaction pressure is 0.4MPa, the circulation time of a circulation system formed by the second super-gravity reactor and a second circulation tank is 80min, the pH value of materials in the reaction system is controlled to be 6-8, the second circulation tank continuously discharges materials to a dilution kettle at the flow rate of 1065g/min, meanwhile, industrial water or washing water is continuously added into the dilution kettle at the flow rate of 2200g/min for cooling and separating, the materials in the dilution kettle are continuously pumped into a centrifuge at the flow rate of 3260g/min through a metering pump, and the finished product of the N-cyanoethyl-N-benzylaniline is obtained through centrifugation and washing.
According to the final product yield, the discharge speed of the N-cyanoethyl-N-benzylaniline can be calculated to be 422g/min, the purity is 96.8 percent, and the yield is 98.5 percent.
Example 2
(1) Cyanoethylation reaction:
the same method as described in example 1;
(2) benzylation reaction:
setting a pump, continuously pumping N-cyanoethylaniline (with the content of 81.5%), benzyl chloride and mother liquor water B (with the content of ammonia water of 12%) into a second supergravity reactor at the flow rates of 317g/min, 240g/min and 600g/min respectively for mixing, wherein the reaction temperature is 95-98 ℃, the reaction pressure is 0.4MPa, the circulation time of a circulation system formed by the second supergravity reactor and a second circulation tank is 90min, the pH value of materials in the reaction system is controlled to be 6-8, the materials in the second circulation tank are continuously discharged to a dilution kettle at the flow rate of 1157g/min, meanwhile, industrial water or washing water is continuously added into the dilution kettle at the flow rate of 2400g/min for cooling and separating materials, the materials in the dilution kettle are continuously pumped into a centrifugal machine at the flow rate of 3550g/min through a metering pump, and N-cyanoethyl-N-benzylaniline finished products are obtained through centrifugation and washing. And pumping the separated mother liquor into a mother liquor B tank through a pump, pumping the mother liquor B tank into a second supergravity reactor through a metering pump after soda is supplemented, pumping washing water into a washing water tank through the pump, and continuously using the washing water for diluting the kettle cooling thinner.
According to the final product yield, the discharge speed of the N-cyanoethyl-N-benzylaniline can be calculated to be 420g/min, the purity is 97.1 percent, and the yield is 98.3 percent.
Comparative example 1
Compared with the example 1, the batch reactor type production process is adopted, a 10000L glass lining reaction kettle is adopted, 1700Kg of aniline, 1000Kg of acrylonitrile and 3250Kg of mother liquor water A are added, the stirring and heating are carried out to 83-85 ℃, the pressure is 0.5-0.8Mpa, the reaction is carried out for 20 hours, and N-cyanoethylaniline is obtained by dilution crystallization, filtration by a centrifuge and water washing. Then putting a single batch of N-cyanoethyl aniline, 2400Kg of benzyl chloride and 5000Kg of mother liquor water B into a 10000L glass lined reaction kettle, stirring and heating to 95-98 ℃, reacting for 25 hours under the pressure of 0.6-0.8Mpa, diluting and crystallizing, filtering by a centrifugal machine, and washing by water to obtain the N-cyanoethyl-N-benzyl aniline. According to the final product yield, 3500Kg of N-cyanoethyl-N-benzylaniline discharge speed, 79.1 percent of purity and 81.7 percent of yield can be calculated.
It should be understood that the above-mentioned embodiments of the present invention are only examples for clearly illustrating the present invention, and are not intended to limit the embodiments of the present invention, and it will be obvious to those skilled in the art that other variations or modifications may be made on the basis of the above description, and all embodiments may not be exhaustive, and all obvious variations or modifications may be included within the scope of the present invention.
Claims (6)
1. A process for producing N-cyanoethyl-N-benzylaniline, comprising:
cyanoethylation reaction: continuously pumping aniline, acrylonitrile and mother liquor water A into a first supergravity reactor for mixing reaction, allowing the obtained reaction mixture A to flow into a first circulating tank, allowing the first circulating tank and the first supergravity reactor to form a first circulating system, discharging after circulating reaction, and performing oil-water separation to obtain N-cyanoethylaniline; the mother liquor A is obtained by mixing a water phase separated from the oil and water with a catalyst and a polymerization inhibitor; the catalyst is a composite catalyst consisting of hydrochloric acid and zinc chloride, the mass concentration of the hydrochloric acid is 30-35 wt%, and the mass ratio of the hydrochloric acid to the zinc chloride is (1-3): 1; the polymerization inhibitor is hydroquinone; the amount of the polymerization inhibitor is 0.1-5% of the mass of the acrylonitrile; the rotating speed of the rotor of the first hypergravity reactor is 500-2800 r/min;
benzylation reaction: continuously pumping the N-cyanoethylaniline, benzyl chloride and mother liquor water B into a second supergravity reactor for mixing reaction, allowing the reaction mixture B to flow into a second circulating tank and enabling the second circulating tank and the second supergravity reactor to form a second circulating system, continuously discharging to a dilution kettle after circulating reaction, cooling, separating materials, centrifuging and washing to obtain the N-cyanoethyl-N-benzylaniline; the mother liquor B is obtained by mixing the water phase obtained by centrifugation with an acid-binding agent, and the feeding amount of the mother liquor B is 1-10 times of the mass of the N-cyanoethylaniline; the molar ratio of the N-cyanoethylaniline to the benzyl chloride is 1: 1-1.5; the rotating speed of the rotor of the second hypergravity reactor is 500-2800 r/min.
2. The method for producing N-cyanoethyl-N-benzylaniline according to claim 1, wherein an acid-binding agent is added during the benzylation reaction to adjust the pH of the benzylation reaction system to 3 to 11.
3. The method for producing N-cyanoethyl-N-benzylaniline according to claim 2, wherein an acid-binding agent is added during the benzylation reaction to adjust the pH of the benzylation reaction system to 6-8.
4. The method for producing N-cyanoethyl-N-benzylaniline according to claim 1, wherein the acid-binding agent is selected from one or more of ammonia water, sodium carbonate and sodium bicarbonate.
5. The method for producing N-cyanoethyl-N-benzylaniline as claimed in claim 1, wherein the hypergravity reactor is a hypergravity rotating packed bed, the rotor speed of the first hypergravity reactor is 1500-2000 r/min, and the rotor speed of the second hypergravity reactor is 1200-2000 r/min.
6. A system for producing N-cyanoethyl-N-benzylaniline, comprising: the system comprises a first hypergravity reactor, a first circulating tank, an oil-water separator, a first mother liquid tank, a second hypergravity reactor, a second circulating tank, a dilution kettle, a second mother liquid tank, a centrifugal machine and a washing tank which are connected in sequence;
the first hypergravity reactor is communicated with a first circulating tank to form circulation, the first circulating tank is communicated with an oil-water separator, a discharge port of the oil-water separator is respectively connected to a feed port of a first mother liquid tank and a feed port of a second hypergravity reactor, and the discharge port of the first mother liquid tank is connected with the feed port of the first hypergravity reactor;
the second hypergravity reactor is communicated with a second circulating tank to form circulation, the second circulating tank is sequentially communicated with the dilution kettle and the centrifugal machine, and a discharge hole of the centrifugal machine is respectively connected to a feed inlet of a second mother liquid tank and a feed inlet of the washing tank.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103539700A (en) * | 2013-10-25 | 2014-01-29 | 浙江迪邦化工有限公司 | Preparation method of N-cyanoethylaniline |
| CN107793328A (en) * | 2016-08-30 | 2018-03-13 | 浙江迪邦化工有限公司 | A kind of production method of N, N cyanoethyl benzylaniline |
| CN109503424A (en) * | 2018-12-10 | 2019-03-22 | 杭州申航新材料有限公司 | N- cyanoethyl-Phenhenzamine production equipment and method |
-
2020
- 2020-01-22 CN CN202010075026.8A patent/CN111205201B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103539700A (en) * | 2013-10-25 | 2014-01-29 | 浙江迪邦化工有限公司 | Preparation method of N-cyanoethylaniline |
| CN107793328A (en) * | 2016-08-30 | 2018-03-13 | 浙江迪邦化工有限公司 | A kind of production method of N, N cyanoethyl benzylaniline |
| CN109503424A (en) * | 2018-12-10 | 2019-03-22 | 杭州申航新材料有限公司 | N- cyanoethyl-Phenhenzamine production equipment and method |
Non-Patent Citations (1)
| Title |
|---|
| N-氰乙基-N-苄基苯胺的工艺研究;王旗;《染料工业》;19921231;第29卷(第4期);第20-21页 * |
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