Production process of N, N-dicyanoethylaniline and N, N-dicyanoethylaniline

By using a zinc chloride catalyst for the cyanoethylation reaction and simplified post-processing steps, the problems of long reaction time and low yield in the synthesis of N,N-dicyanoethylaniline are solved, and an efficient and simplified production process is achieved. , improving product purity and yield.

CN119330856APending Publication Date: 2025-01-21YANTAI ANOKY FINE CHEM CO LTD
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Patent Information

Application Number
CN202411451261.5
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2024-10-17
Publication Date
2025-01-21

AI Technical Summary

Technical Problem

The synthesis of N,N-dicyanoethyl aniline has problems such as long reaction time, complex post-treatment process, catalyst stability and safety problems, low yields and difficult reaction control, which limits the synthesis efficiency and widespread industrial application.

Method used

Zinc chloride is used as a catalyst to generate N,N-dicyanoethylaniline through cyanoethylation reaction, and the post-treatment process is simplified through vacuum distillation and cooling crystallization steps to improve reaction efficiency and yield.

Benefits of technology

The reaction time is shortened, the production efficiency is improved, the operation process is simplified, the use of chemical reagents and waste water discharge are reduced, the direct output of high-purity products is achieved, the yield is increased, and the waste of raw materials is reduced.

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Abstract

The invention provides a production process of N, N-dicyanoethylaniline and the N, N-dicyanoethylaniline, and particularly relates to the technical field of organic synthesis. The production process comprises the following steps: A, adding acrylonitrile, a catalyst, a polymerization inhibitor and water into a container, uniformly stirring, then dropwise adding aniline, and carrying out cyanoethylation reaction to generate a mixed solution containing N, N-dicyanoethylaniline; b, carrying out reduced pressure distillation on the mixed solution to obtain a fraction and a substrate, mechanically applying the fraction which is unreacted acrylonitrile to the next batch, adding water into the substrate, crystallizing, and filtering to obtain N, N-dicyanoethylaniline and a mother solution; wherein the catalyst is zinc chloride and hydrochloric acid. According to the production process of the N, N-dicyanoethylaniline, provided by the invention, the zinc chloride is used for replacing aluminum chloride as a catalyst, so that the reaction time is shortened to 4-8 hours, and the production efficiency is greatly improved. And the process is simplified in the post-treatment stage, and direct production of high-purity products is realized.
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Description

Technical Field

[0001] The invention relates to the technical field of organic synthesis, in particular to a production process of N,N-dicyanoethylaniline and N,N-dicyanoethylaniline. Background Art

[0002] As an important intermediate of azo disperse dyes, N,N-dicyanoethylaniline plays a key role in the synthesis of dyes such as Disperse Yellow 163 and Disperse Orange 40. Its preparation method has always been the focus of attention in the chemical industry. In the prior art, the synthesis of N,N-dicyanoethylaniline usually faces some challenges and limitations.

[0003] First, the traditional synthesis method uses aniline and acrylonitrile as raw materials, zinc chloride and aluminum chloride as catalysts. The reaction takes more than ten hours, and the post-processing process is complicated, requiring acid washing and water washing to obtain the final product. This method is not only time-consuming, but the catalyst aluminum chloride used has poor stability during storage and use, poses a safety hazard, and is rarely used in industry. In addition, the high catalytic activity of aluminum chloride may make the reaction difficult to control and easily induce side reactions.

[0004] In addition, although the use of microchannel technology in the synthesis of N,N-dicyanoethylaniline can speed up the reaction and shorten the reaction time, the yield of this method is low, only about 75%. This shows that in the synthesis process, the raw material conversion rate is not high, resulting in a waste of raw materials and an increase in production costs.

[0005] In summary, the challenges and limitations faced by the synthesis of N,N-dicyanoethylaniline mainly include long reaction time, complex post-treatment process, catalyst stability and safety issues, low yield and difficult reaction control, etc. These problems limit the synthesis efficiency and the wide range of industrial applications.

[0006] In view of this, the present invention is proposed. Summary of the invention

[0007] One of the purposes of the present invention is to provide a production process of N,N-dicyanoethylaniline to alleviate at least one of the above technical problems in the prior art.

[0008] A second object of the present invention is to provide an N,N-dicyanoethylaniline.

[0009] In order to achieve the above-mentioned purpose of the present invention, the following technical solutions are particularly adopted:

[0010] The first aspect of the present invention provides a production process of N,N-dicyanoethylaniline, comprising the following steps:

[0011] A. Add acrylonitrile, catalyst, inhibitor and water into a container and stir evenly, then drop aniline to carry out cyanoethylation reaction to generate a mixed solution containing N,N-dicyanoethylaniline;

[0012] B. performing reduced pressure distillation on the mixed solution to obtain a fraction and a substrate, wherein the fraction is unreacted acrylonitrile and is used in the next batch, and water is added to the substrate for crystallization and filtration to obtain N,N-dicyanoethylaniline and a mother liquor;

[0013] Wherein, the catalyst is zinc chloride and hydrochloric acid.

[0014] Furthermore, the polymerization inhibitor includes hydroquinone.

[0015] Further, in step A, the molar ratio of the aniline to the acrylonitrile is 1:

[0016] (2.2~3.0).

[0017] Furthermore, the temperature of the cyanoethylation reaction is 60-120° C., and the time is 4-8 hours.

[0018] Preferably, the temperature of the cyanoethylation reaction is 80-100°C.

[0019] Furthermore, the hydrochloric acid accounts for 1 to 4 wt % in the reaction system.

[0020] Preferably, the zinc chloride accounts for 10-30 wt % in the reaction system.

[0021] Furthermore, the water accounts for 5 to 25 wt% in the reaction system;

[0022] The polymerization inhibitor accounts for 0.1-0.3 wt % in the reaction system.

[0023] Furthermore, the crystallization temperature is 40-100° C. and the crystallization time is 1-3 hours.

[0024] Preferably, during the crystallization process, the amount of water added is 1.5 to 2.5 times the mass of the aniline.

[0025] Furthermore, the production process of the present invention further comprises the following steps after step B:

[0026] C. Applying the mother liquor and the unreacted acrylonitrile to the next batch, adding acrylonitrile and water and stirring evenly, and then dropping aniline to carry out cyanoethylation reaction to generate a mixed solution containing N,N-dicyanoethylaniline;

[0027] D. Cycle steps B and C;

[0028] Preferably, in step C, the molar ratio of aniline to acrylonitrile in the system is 1:(2.2-3.0).

[0029] The second aspect of the present invention provides N,N-dicyanoethylaniline, which is produced by the production process described in the first aspect.

[0030] Furthermore, the purity of the N,N-dicyanoethylaniline is greater than 98%.

[0031] Compared with the prior art, the present invention has at least the following beneficial effects:

[0032] The production process of N,N-dicyanoethylaniline provided by the present invention uses zinc chloride instead of aluminum chloride as a catalyst, simplifies catalyst management, and reduces potential safety hazards in the production process. The reaction time is shortened to 4-8 hours, greatly improving production efficiency. In the post-processing stage, cooling crystallization is used to replace the traditional complex pickling steps, simplifying the operation process, reducing the use of chemical reagents and wastewater discharge, and achieving direct output of high-purity products.

[0033] The N,N-dicyanoethylaniline provided by the present invention has a purity of more than 98%, and the impurity content is low, which can meet the needs of high-performance applications. The yield is higher than 95%, which reduces the waste of raw materials, reduces the preparation cost, and is conducive to large-scale production and cost control. The N,N-dicyanoethylaniline of the present invention has a wide range of application potentials as a catalyst or intermediate in organic synthesis, and can promote the progress of certain chemical reactions, such as acylation, hydroxycarbonylation of aromatic aldehydes, etc., further enhancing its competitiveness in the market. BRIEF DESCRIPTION OF THE DRAWINGS

[0034] In order to more clearly illustrate the specific implementation methods of the present invention or the technical solutions in the prior art, the drawings required for use in the specific implementation methods or the description of the prior art will be briefly introduced below. Obviously, the drawings described below are some implementation methods of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without paying creative work.

[0035] Figure 1 The present invention provides a continuous production process flow chart of N,N-dicyanoethylaniline. DETAILED DESCRIPTION

[0036] The embodiments of the present invention will be described in detail below in conjunction with the embodiments and examples, but those skilled in the art will understand that the following embodiments and examples are only used to illustrate the present invention and should not be considered to limit the scope of the present invention. Based on the embodiments in the present invention, all other embodiments obtained by ordinary technicians in this field without making creative work are within the scope of protection of the present invention.

[0037] The first aspect of the present invention provides a production process of N,N-dicyanoethylaniline, comprising the following steps:

[0038] A. Add acrylonitrile, catalyst, inhibitor and water into a container and stir evenly, then drop aniline to carry out cyanoethylation reaction to generate a mixed solution containing N,N-dicyanoethylaniline;

[0039] B. performing reduced pressure distillation on the mixed solution to obtain a fraction and a substrate, wherein the fraction is unreacted acrylonitrile and is used in the next batch, and water is added to the substrate for crystallization and filtration to obtain N,N-dicyanoethylaniline and a mother liquor;

[0040] Wherein, the catalyst is zinc chloride and hydrochloric acid.

[0041] The production process of N,N-dicyanoethylaniline provided by the present invention uses zinc chloride instead of aluminum chloride as a catalyst, simplifies catalyst management, and reduces potential safety hazards in the production process. The reaction time is shortened to 4-8 hours, greatly improving production efficiency. In the post-processing stage, cooling crystallization is used to replace the traditional complex pickling steps, simplifying the operation process, reducing the use of chemical reagents and wastewater discharge, and achieving direct output of high-purity products.

[0042] Specifically, the method for synthesizing N,N-dicyanoethylaniline provided by the present invention has significant advantages, which are mainly manifested in the following aspects:

[0043] First, this method avoids the use of aluminum chloride in the traditional method by using only zinc chloride as the Lewis acid catalyst, thereby reducing safety hazards in the production process. This improvement not only improves production safety, but also simplifies the selection and management of catalysts.

[0044] Secondly, the reaction time of this synthesis method is significantly shortened to 4-8 hours, which is much faster than the traditional method of more than ten hours, thereby significantly improving the reaction efficiency and production capacity.

[0045] In terms of post-processing, this method adopts the method of cooling crystallization, which is simple to operate and does not require complicated pickling steps. This not only reduces the difficulty of operation, but also reduces the use of chemical reagents and corresponding wastewater discharge.

[0046] In addition, the process uses hydrochloric acid as a catalyst in the reaction and washes away impurities during the cooling crystallization process, so that N,N-dicyanoethylaniline with a purity of more than 98% can be obtained without additional acid washing, which further improves the purity and quality of the product. Using hydrochloric acid as a catalyst, impurities are washed away during the cooling crystallization, so that N,N-dicyanoethylaniline with a purity of more than 98% can be obtained without acid washing.

[0047] The efficiency of water resource utilization has also been significantly improved, because the water used for washing can be recycled for subsequent experiments, greatly reducing the generation of three wastes, reflecting the concept of environmental protection and sustainability.

[0048] In terms of yield, the yield of the product obtained by this process is very high, reaching more than 95%, which is much higher than the yield of traditional methods, which means less waste of raw materials and higher economic benefits.

[0049] The high purity of N,N-dicyanoethylaniline is due to the high conversion rate of the reaction and the dual effect of using hydrochloric acid as a catalyst, which not only promotes the thoroughness of the reaction but also effectively removes impurities during the crystallization process.

[0050] Furthermore, the polymerization inhibitor includes hydroquinone.

[0051] Further, in step A, the molar ratio of the aniline to the acrylonitrile is 1:

[0052] (2.2~3.0).

[0053] The specific reaction formulas are shown in the following reaction formulas Ⅰ and Ⅱ:

[0054]

[0055] In the process of aniline and acrylonitrile reacting to generate N, N-dicyanoethylaniline, although the theoretical molar ratio is 1:2, the present invention sets acrylonitrile to be excessive, mainly to ensure that the aniline can react as completely as possible. Since the dicyanoethylation of aniline requires two acrylonitrile molecules, excessive acrylonitrile helps to promote the reaction in the direction of generating more N, N-dicyanoethylaniline, thereby improving the conversion rate of the reaction and the selectivity of the product. In addition, excessive acrylonitrile can also reduce the occurrence of side reactions and simplify the separation and purification steps of the product in the post-processing process.

[0056] Typically but not limiting, the molar ratio of aniline to acrylonitrile can be, for example, 1:2.2, 1:2.3, 1:2.4, 1:2.5, 1:2.6, 1:2.7, 1:2.8 or 1:3.0, or any value within the range of 1:(2.2-3.0).

[0057] Furthermore, the temperature of the cyanoethylation reaction is 60-120° C., and the time is 4-8 hours.

[0058] The temperature of the cyanoethylation reaction is 60-120°C, which is conducive to the chemical reaction between aniline and acrylonitrile, ensuring the full progress of the reaction, while avoiding side reactions or uncontrollable rapid reactions that may be caused by excessively high temperatures. The cyanoethylation reaction time of 4-8 hours provides a guarantee for full contact and reaction between the reactant molecules, which helps to improve the conversion rate of the reaction and the selectivity of the product. By controlling the reaction time, the reaction process can be finely regulated to ensure that the aniline and acrylonitrile in the reactants are fully utilized and reduce the waste of raw materials. At the same time, this time range helps to control the reaction rate and avoid operational difficulties and safety hazards caused by too fast a reaction speed.

[0059] Preferably, the temperature of the cyanoethylation reaction is 80-100°C.

[0060] Typically but not limiting, the temperature of the cyanoethylation reaction can be, for example, 60°C, 70°C, 80°C, 90°C, 100°C, 110°C or 120°C, or any value within the range of 60°C to 120°C; the time can be, for example, 4 hours, 5 hours, 6 hours, 7 hours or 8 hours, or any value within the range of 4 hours to 8 hours. Preferably, the reaction temperature can be, for example, 80°C, 85°C, 90°C, 95°C or 100°C, or any value within the range of 80°C to 100°C.

[0061] Furthermore, the hydrochloric acid accounts for 1 to 4 wt % in the reaction system.

[0062] In this specification, the "reaction system" refers to the environment for the cyanoethylation reaction, which is composed of acrylonitrile, a catalyst, an inhibitor, water and aniline.

[0063] Typically but not limiting, the proportion of hydrochloric acid in the reaction system may be, for example, 1 wt%, 1.5 wt%, 2 wt%, 2.5 wt%, 3 wt% or 4 wt%, or any value within the range of 1 wt% to 4 wt%.

[0064] Preferably, the zinc chloride accounts for 10 to 30 wt % in the reaction system.

[0065] Typically but not limiting, the proportion of zinc chloride in the reaction system may be, for example, 10 wt%, 15 wt%, 20 wt%, 25 wt% or 30 wt%, or any value within the range of 10 wt% to 30 wt%.

[0066] Furthermore, the water accounts for 5 to 25 wt % in the reaction system. The presence of water helps to dissolve zinc chloride. When zinc chloride is dissolved, the reaction rate and efficiency can be increased.

[0067] Typically but not limiting, the proportion of water in the reaction system may be, for example, 5 wt%, 10 wt%, 15 wt%, 20 wt% or 25 wt%, or any value within the range of 5 wt% to 25 wt%.

[0068] The polymerization inhibitor accounts for 0.1-0.3 wt % in the reaction system.

[0069] Typically but not limiting, the proportion of the polymerization inhibitor in the reaction system may be, for example, 0.1 wt%, 0.2 wt% or 0.3 wt%, or any value within the range of 0.1 wt% to 0.3 wt%.

[0070] Furthermore, the crystallization temperature is 40-100° C. and the crystallization time is 1-3 hours.

[0071] Typically but not limiting, the crystallization temperature can be, for example, 40°C, 50°C, 60°C, 70°C, 80°C, 90°C or 100°C, or any value within the range of 40°C to 100°C; the crystallization time can be, for example, 1 hour, 1.5 hours, 2 hours or 3 hours, or any value within the range of 1 hour to 3 hours.

[0072] Furthermore, during the crystallization process, the amount of water added is 1.5 to 2.5 times the mass of the aniline.

[0073] Typically but not limiting, during the crystallization process, the amount of water added is 1.5 times, 1.75 times, 2 times, 2.25 times or 2.5 times the mass of the aniline, and can also be any value within the range of 1.5 to 2.5 times.

[0074] Furthermore, the present invention provides a continuous production process of N,N-dicyanoethylaniline, such as Figure 1 As shown, the following steps are included:

[0075] A. Add acrylonitrile, catalyst, inhibitor and water into a container and stir evenly, then drop aniline to carry out cyanoethylation reaction to generate a mixed solution containing N,N-dicyanoethylaniline;

[0076] B. performing reduced pressure distillation on the mixed solution to obtain a fraction and a substrate, wherein the fraction is unreacted acrylonitrile and is used in the next batch, and water is added to the substrate for crystallization and filtration to obtain N,N-dicyanoethylaniline and a mother liquor;

[0077] C. Applying the mother liquor and the unreacted acrylonitrile to the next batch, adding acrylonitrile and water and stirring evenly, and then dropping aniline to carry out cyanoethylation reaction to generate a mixed solution containing N,N-dicyanoethylaniline;

[0078] D. Cycle steps B and C;

[0079] Wherein, the catalyst is zinc chloride and hydrochloric acid.

[0080] By recycling the mother liquor and the fraction, the generation of the three wastes is further reduced. In addition, the continuous production process of the present invention recycles the unreacted acrylonitrile and the mother liquor, improves the utilization rate of the raw materials, reduces the discharge of chemical wastes, ensures the continuity and efficiency of production, reduces the production cost, and reduces the impact on the environment.

[0081] The recycling strategy in the entire process, including the recycling of catalysts and inhibitors, as well as the recycling of crystallization and washing water, not only reduces costs but also reduces the generation of wastewater, reflecting the efficient use of resources and environmental protection.

[0082] Preferably, in step C, the molar ratio of aniline to acrylonitrile in the system is 1:(2.2-3.0).

[0083] In the cyanoethylation reaction in step C, acrylonitrile in the fraction is recycled. After the acrylonitrile is supplemented, the molar ratio of aniline to acrylonitrile in the system can also be 1:2.2, 1:2.3, 1:2.4, 1:2.5, 1:2.6, 1:2.7, 1:2.8 or 1:3.0, or any value within the range of 1:(2.2-3.0).

[0084] The second aspect of the present invention provides N,N-dicyanoethylaniline, which is produced by the production process described in the first aspect.

[0085] The N,N-dicyanoethylaniline provided by the present invention has a purity of more than 98%, and the impurity content is low, which can meet the needs of high-performance applications. The yield is higher than 95%, which reduces the waste of raw materials, reduces the preparation cost, and is conducive to large-scale production and cost control. The N,N-dicyanoethylaniline of the present invention has a wide range of application potentials as a catalyst or intermediate in organic synthesis, and can promote the progress of certain chemical reactions, such as acylation, hydroxycarbonylation of aromatic aldehydes, etc., further enhancing its competitiveness in the market.

[0086] Furthermore, the purity of the N,N-dicyanoethylaniline is greater than 98%.

[0087] The present invention is further described below by specific examples and comparative examples, but it should be understood that these examples are only used for more detailed description and should not be understood as limiting the present invention in any form. The raw materials used in the examples and comparative examples of the present invention, if no specific conditions are specified, are carried out according to conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used without indicating the manufacturer are all conventional products that can be purchased commercially.

[0088] Example 1

[0089] This embodiment provides a N,N-dicyanoethylaniline, and the production process is as follows:

[0090] 1. Add 100 g aniline, 170 g acrylonitrile, 109.4 g zinc chloride, 15 g hydrochloric acid (mass concentration is 31%), 1.2 g hydroquinone and 90 g water into a four-necked flask and react at 90°C for 6 h.

[0091] 2. After the reaction, the mixed solution was distilled under reduced pressure to remove the unreacted acrylonitrile. The collected amount of unreacted acrylonitrile was 61.2 g. 180 g of water was added to the substrate, stirred at 60° C. for 2 h, filtered and washed with water to obtain 211.55 g of N,N-dicyanoethylaniline and 221 g of mother liquor.

[0092] 3. Add 121.4 g of mother liquor and 61.2 g of unreacted acrylonitrile into a four-necked flask, supplement with 108.8 g of acrylonitrile and 78.0 g of zinc chloride, then add 100 g of aniline, 15 g of hydrochloric acid and 1.2 g of hydroquinone and react at 90 °C for 6 h.

[0093] 4. After the reaction, the mixed solution was distilled under reduced pressure to remove the unreacted acrylonitrile. 180 g of water was added to the substrate, stirred at 60° C. for 2 h, filtered and washed with water to obtain 211.6 g of N,N-dicyanoethylaniline, with a yield of 98.9%.

[0094] Example 2

[0095] This embodiment provides a N,N-dicyanoethylaniline, and the production process is as follows:

[0096] 1. The difference from this step in Example 1 is that the amount of acrylonitrile added is 137 g, and the other raw materials and amounts are the same as those in this step in Example 1.

[0097] 2. After the reaction, the mixed solution was distilled under reduced pressure to remove the unreacted acrylonitrile. The collected amount of unreacted acrylonitrile was 29.7 g. 180 g of water was added to the substrate, stirred at 60° C. for 2 h, filtered and washed with water to obtain 207.06 g of N,N-dicyanoethylaniline and 253 g of mother liquor, with a yield of 96.8%.

[0098] 3. Add 120.14 g of mother liquor and 29.7 g of unreacted acrylonitrile into a four-necked flask, supplement with 107.3 g of acrylonitrile and 79.3 g of zinc chloride, then add 100 g of aniline and 15 g of hydrochloric acid and react at 90°C for 6 hours.

[0099] 4. After the reaction, the mixed solution was distilled under reduced pressure to remove the unreacted acrylonitrile. 180 g of water was added to the substrate, stirred at 60° C. for 2 h, filtered and washed with water to obtain 207.02 g of N,N-dicyanoethylaniline, with a yield of 96.8%.

[0100] Example 3

[0101] This embodiment provides a N,N-dicyanoethylaniline, and the production process is as follows:

[0102] 1. The difference from this step in Example 1 is that the amount of hydrochloric acid (mass concentration is 31%) added is 12 g, and the other raw materials and amounts are the same as those in this step in Example 1.

[0103] 2. After the reaction, the mixed solution was distilled under reduced pressure to remove the unreacted acrylonitrile. The collected amount of unreacted acrylonitrile was 61.9 g. 180 g of water was added to the substrate, stirred at 60° C. for 2 h, filtered and washed with water to obtain 208.12 g of N,N-dicyanoethylaniline and 223 g of mother liquor, with a yield of 97.2%.

[0104] Example 4

[0105] This embodiment provides a N,N-dicyanoethylaniline, and the production process is as follows:

[0106] 1. The difference from this step in Example 3 is that the amount of zinc chloride added is 72.8 g, and the other raw materials and amounts are the same as those in this step in Example 3.

[0107] 2. After the reaction, the mixed solution was distilled under reduced pressure to remove the unreacted acrylonitrile. The collected amount of unreacted acrylonitrile was 63.2 g. 180 g of water was added to the substrate, stirred at 60° C. for 2 h, filtered and washed with water to obtain 204.06 g of N,N-dicyanoethylaniline and 220 g of mother liquor, with a yield of 95.4%.

[0108] Example 5

[0109] This embodiment provides an N,N-dicyanoethylaniline. The difference from Embodiment 1 is that the amount of acrylonitrile added is 125.2 g, and the total amount of acrylonitrile after acrylonitrile is supplemented in step 3 is 125.2 g. The remaining raw materials and steps are the same as those in Embodiment 1 and will not be described again.

[0110] The yield was 198.9 g, the yield was 93.0%, and the purity was 99.3%.

[0111] Comparative Example 1 (without addition of hydrochloric acid)

[0112] This comparative example provides a N,N-dicyanoethylaniline, and the production process is as follows:

[0113] 100 g of aniline, 170 g of acrylonitrile, 109.4 g of zinc chloride, 1.2 g of hydroquinone and 90 g of water were added to a four-necked flask and kept at 90° C. for 6 h. After the reaction, samples were taken for HPLC detection and it was found that the content of N,N-dicyanoethylaniline in the reaction system was only 26%, so no post-treatment step was performed.

[0114] Comparative Example 2 (without zinc chloride)

[0115] This comparative example provides a N,N-dicyanoethylaniline, and the production process is as follows:

[0116] 100 g of aniline, 170 g of acrylonitrile, 15 g of hydrochloric acid (mass fraction 31%), 1.2 g of hydroquinone and 90 g of water were added to a four-necked flask and kept at 90° C. for 6 h. After the reaction, samples were taken for HPLC detection and it was found that no N,N-dicyanoethylaniline was generated in the reaction system, so no post-treatment step was performed.

[0117] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention, rather than to limit it. Although the present invention has been described in detail with reference to the aforementioned embodiments, those skilled in the art should understand that they can still modify the technical solutions described in the aforementioned embodiments, or replace some or all of the technical features therein with equivalents. However, these modifications or replacements do not cause the essence of the corresponding technical solutions to deviate from the scope of the technical solutions of the embodiments of the present invention.

Claims

1. A production process of N,N-dicyanoethylaniline, characterized in that: The following steps are involved: A. Add acrylonitrile, catalyst, inhibitor and water into a container and stir evenly, then drop aniline to carry out cyanoethylation reaction to generate a mixed solution containing N,N-dicyanoethylaniline; B. performing reduced pressure distillation on the mixed solution to obtain a fraction and a substrate, wherein the fraction is unreacted acrylonitrile and is used in the next batch, and water is added to the substrate for crystallization and filtration to obtain N,N-dicyanoethylaniline and a mother liquor; Wherein, the catalyst is zinc chloride and hydrochloric acid.

2. The production process according to claim 1, characterized in that: The polymerization inhibitor includes hydroquinone.

3. The production process according to claim 1, characterized in that: In step A, the molar ratio of the aniline to the acrylonitrile is 1:(2.2-3.0).

4. The production process according to claim 1, characterized in that: The temperature of the cyanoethylation reaction is 60 to 120° C. and the time is 4 to 8 hours; Preferably, the temperature of the cyanoethylation reaction is 80-100°C.

5. The production process according to claim 1, characterized in that: The hydrochloric acid accounts for 1 to 4 wt% in the reaction system; Preferably, the zinc chloride accounts for 10 to 30 wt % in the reaction system.

6. The production process according to claim 1, characterized in that: The water accounts for 5 to 25 wt% in the reaction system; The polymerization inhibitor accounts for 0.1-0.3 wt % in the reaction system.

7. The production process according to claim 1, characterized in that: The crystallization temperature is 40-100°C and the time is 1-3h; Preferably, during the crystallization process, the amount of water added is 1.5 to 2.5 times the mass of the aniline.

8. The production process according to any one of claims 1 to 6, characterized in that: The following steps are also included after step B: C. applying the mother liquor and the unreacted acrylonitrile to the next batch, adding acrylonitrile and water and stirring evenly, and then dropping aniline to carry out cyanoethylation reaction to generate a mixed solution containing N,N-dicyanoethylaniline; D. Cycle steps B and C; Preferably, in step C, the molar ratio of aniline to acrylonitrile in the system is 1:(2.2-3.0).

9. An N,N-dicyanoethylaniline, characterized in that The product is produced by the production process described in any one of claims 1 to 8.

10. The N,N-dicyanoethylaniline according to claim 9, characterized in that Purity>98%.