CN110872236A - N-cyanoethyl-N-benzylaniline and preparation method and application thereof - Google Patents
N-cyanoethyl-N-benzylaniline and preparation method and application thereof Download PDFInfo
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- CN110872236A CN110872236A CN201811004781.6A CN201811004781A CN110872236A CN 110872236 A CN110872236 A CN 110872236A CN 201811004781 A CN201811004781 A CN 201811004781A CN 110872236 A CN110872236 A CN 110872236A
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- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
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Abstract
The invention relates to N-cyanoethyl-N-benzylaniline and a preparation method and application thereof. The preparation method comprises the following steps: the reaction steps are as follows: adding water, cyanoethylaniline, benzyl chloride and soda ash into a reaction kettle for reaction to obtain a reaction product; standing: continuously adding water into the reaction kettle, uniformly mixing, standing and layering to obtain a water phase and an organic phase; a distillation step: and distilling the organic phase, and removing fractions to obtain a distillation product. According to the preparation method of the N-cyanoethyl-N-benzylaniline, the prepared N-cyanoethyl-N-benzylaniline is low in the content of the chlorinated benzene and the chlorinated toluene, so that the dye is convenient to produce, and the content of the chlorinated benzene and the chlorinated toluene on the fabric dyed by the dye synthesized from the intermediate N-cyanoethyl-N-benzylaniline does not exceed the limit requirement of Oeko-Tex Standard 100.
Description
Technical Field
The invention relates to N-cyanoethyl-N-benzylaniline and a preparation method and application thereof, belonging to the field of chemical synthesis.
Background
At present, green textiles and environment-friendly dyes become the key points for the development of textile industry and dye industry, and the environment-friendly dyes are one of the important conditions for ensuring the green textiles. N-cyanoethyl-N-benzylaniline is an important organic intermediate and is widely applied to the synthesis of disperse dyes. The N-cyanoethyl-N-benzylaniline is generally a white powder with a melting point of 97.2 to 102.3 ℃.
The environment-friendly dye needs to meet the requirements of environment-friendly quality besides necessary use process applicability, application performance and fastness performance. The environmental quality has practical indexes and contents, and is related to the structure of the dye, such as: the environmental-friendly dye requires that the azo dye which can not decompose and release 22 carcinogenic aromatic amines under specific conditions can not be carcinogenic; must be a non-allergenic dye, a non-acute toxic dye; the content of heavy metals contained is below a limit value, and the like. On the other hand, it is concerned with external factors such as the generation of side reactions during the production of dyes, unreacted raw materials, additional additives and auxiliaries, for example: the environment-friendly dye is required to be free of environmental hormone; the material does not contain chemical substances which can cause environmental pollution, such as volatile organic compounds, chlorine-containing carriers and the like; free of variability compounds and persistent organic pollutants; does not contain limited pesticides, etc.
The N-cyanoethyl-N-benzylaniline synthesized by the existing method often contains a large amount of compounds such as chlorobenzene and chlorotoluene, and the content of chlorobenzene and chlorotoluene on the fabric dyed by the dye synthesized by the intermediate exceeds the limit requirement of Oeko-Tex Standard 100.
Disclosure of Invention
Problems to be solved by the invention
In view of the technical problems in the prior art, such as that the synthesized N-cyanoethyl-N-benzylaniline contains a large amount of chlorobenzene, toluene chloride and the like, and the content of the chlorobenzene and the toluene chloride on the fabric dyed by the dye synthesized by the intermediate exceeds the limit requirement of an Oeko-Tex Standard100, the invention provides a preparation method of the N-cyanoethyl-N-benzylaniline.
Furthermore, the invention also provides N-cyanoethyl-N-benzylaniline, wherein the content of chlorinated benzene and chlorinated toluene is low.
Means for solving the problems
The invention relates to a preparation method of N-cyanoethyl-N-benzylaniline, which comprises the following steps:
the reaction steps are as follows: adding water, cyanoethylaniline, benzyl chloride and sodium carbonate into a reaction kettle for reaction to obtain a reaction product;
standing: continuously adding water into the reaction kettle, uniformly mixing, standing and layering to obtain a water phase and an organic phase;
a distillation step: and distilling the organic phase, and removing fractions to obtain a distillation product.
According to the preparation method, in the reaction step, the adding amount of water is 50-100% of the weight of the N-cyanoethylaniline; the mol ratio of the N-cyanoethylaniline to the benzyl chloride to the sodium carbonate is 1: 1.0-1.1: 0.5 to 0.6.
According to the preparation method, in the standing step, the adding amount of the water is 50-150% of the weight of the N-cyanoethylaniline.
The production method according to the present invention, wherein the distillation step comprises: starting jacket steam, heating to 100-160 ℃, and then starting straight-through steam for distillation; preferably, the distillation comprises atmospheric distillation or vacuum distillation.
The preparation method according to the present invention, wherein, in the reaction step, the reaction temperature is 90 ℃ to 120 ℃, preferably 100 ℃ to 110 ℃.
The preparation method according to the present invention, wherein, in the standing step, the temperature of the reaction kettle is controlled to be between 90 ℃ and 110 ℃, preferably between 95 ℃ and 105 ℃.
The preparation method according to the present invention, wherein the preparation method further comprises:
a precipitation step: adding water into the distillation product, and cooling the distillation product to separate out the N-cyanoethyl-N-benzylaniline.
The invention also provides N-cyanoethyl-N-benzylaniline, which is prepared according to the preparation method disclosed by the invention.
The N-cyanoethyl-N-benzylaniline according to the present invention is characterized in that the sum of the contents of monochlorotoluene and dichlorotoluene in the N-cyanoethyl-N-benzylaniline is 50ppm or less, preferably 20ppm or less, and more preferably 10ppm or less.
The invention also provides the application of the N-cyanoethyl-N-benzylaniline prepared by the preparation method or the N-cyanoethyl-N-benzylaniline prepared by the preparation method in preparing dye.
ADVANTAGEOUS EFFECTS OF INVENTION
According to the preparation method of the N-cyanoethyl-N-benzylaniline, the prepared N-cyanoethyl-N-benzylaniline is low in the content of the chlorinated benzene and the chlorinated toluene, so that the dye is convenient to produce, and the content of the chlorinated benzene and the chlorinated toluene on the fabric is not more than the limit requirement of Oeko-Tex Standard100 after the dye synthesized by the intermediate N-cyanoethyl-N-benzylaniline is dyed.
Detailed Description
Various exemplary embodiments, features and aspects of the invention will be described in detail below. The word "exemplary" is used exclusively herein to mean "serving as an example, embodiment, or illustration. Any embodiment described herein as "exemplary" is not necessarily to be construed as preferred or advantageous over other embodiments.
Furthermore, in the following detailed description, numerous specific details are set forth in order to provide a better understanding of the present invention. It will be understood by those skilled in the art that the present invention may be practiced without some of these specific details. In other instances, methods, means, devices and steps which are well known to those skilled in the art have not been described in detail so as not to obscure the invention.
The invention provides a preparation method of N-cyanoethyl-N-benzylaniline, which comprises the following steps:
the reaction steps are as follows: adding water, cyanoethylaniline, benzyl chloride and sodium carbonate into a reaction kettle for reaction to obtain a reaction product;
standing: continuously adding water into the reaction kettle, uniformly mixing, standing and layering to obtain a water phase and an organic phase;
a distillation step: the organic phase is distilled (for example, by transferring the organic phase to an evaporation vessel, introducing steam and distilling), and after removal of the distillate, a distillate is obtained.
In the reaction step, water, cyanoethylaniline, benzyl chloride and soda ash are subjected to a chemical reaction to produce cyanoethyl-benzylaniline. In the invention, the temperature of the reaction kettle can be slowly raised to a certain temperature (for example, 90-120 ℃), and then the reaction is carried out with heat preservation until the reaction end point, so as to reduce the generation of impurities. Specifically, in the reaction step, the temperature for the heat preservation reaction may be 90 to 120 ℃, preferably 100 to 110 ℃, so that water, cyanoethylaniline, benzyl chloride and soda ash can be fully reacted. Generally, sampling can be carried out to detect whether the purity is qualified, wherein when the purity (HPLC) of the raw material N-cyanoethylaniline is less than or equal to 3 percent, the reaction can be indicated to be complete.
Further, in the reaction step of the present invention, the amount of the added water is 50% to 100% by weight of the cyanoethylaniline, for example: 55%, 65%, 75%, 85%, 95%, etc.; the mol ratio of the N-cyanoethylaniline to the benzyl chloride to the sodium carbonate is 1: 1.0-1.1: 0.5 to 0.6.
In the standing step, the adding amount of the water is 50-150% of the weight of the N-cyanoethylaniline, such as: 60%, 70%, 80%, 90%, 100%, 110%, 120%, 130%, 140%, etc. The invention further adds water for even mixing, thereby effectively layering the reaction product and the water phase to obtain the water phase and the organic phase. Generally, the upper layer is an organic phase and the lower layer is an aqueous phase, and the lower aqueous phase may be separated first and then the organic phase may be transferred to an evaporation kettle.
In the present invention, in the standing step, the temperature of the reaction kettle is controlled between 90 ℃ and 110 ℃, preferably between 95 ℃ and 105 ℃, the standing time may be between 0.5 hour and 2 hours, stirring may be performed after adding water before standing so that the added water and the reaction product can be mixed uniformly, and the stirring time may be between 0.5 hour and 2 hours.
The distillation step of the present invention comprises: the jacket steam was started and the temperature was raised to 100 to 160 c (in this case, the distillate amount was reduced). After the distillate (i.e., distillate) was decreased in amount, the straight-through steam was turned on to continue the distillation. Generally speaking, after the straight-through steam distillation is started, with the increase of the distillate quantity of the fraction, the contents of chlorobenzene and toluene chloride in the fraction can be continuously sampled and detected (the contents of chlorobenzene and toluene chloride in the fraction can be detected, and the contents of chlorobenzene and toluene chloride in the distillation product can also be detected), and when the contents of chlorobenzene and toluene chloride are not changed twice continuously, the distillation can be stopped.
Preferably, the distillation comprises atmospheric distillation or vacuum distillation; specifically, the temperature of the distillation step is from 100 ℃ to 160 ℃, for example: 110 ℃, 140 ℃, 150 ℃, and the like, preferably 100-130 ℃; namely, the temperature can be raised to 100-160 ℃ by using jacket steam. Organic impurities such as benzene chloride, toluene chloride and the like in the N-cyanoethyl-N-benzylaniline obtained in the reaction step can be effectively removed through the distillation step, so that the environment-friendly N-cyanoethyl-N-benzylaniline with high purity is obtained.
In the invention, the jacket steam is used for slowly raising the temperature, and then the straight-through steam is used for continuously distilling, so that the heating can be more thorough. More benzene chloride and toluene chloride can be brought out from the distillate, and the purity of the N-cyanoethyl-N-benzylaniline in the distillation product is higher.
Further, the preparation method of the present invention further comprises a precipitation step: adding water into the distillation product, and cooling the distillation product to separate out the N-cyanoethyl-N-benzylaniline. In the invention, the separation step can be carried out in a material separating pot, namely water is added into the material separating pot, then the distillation product is transferred into the material separating pot and cooled to 50-60 ℃, the material separation is carried out, the N-cyanoethyl-N-benzylaniline is separated out and then filtered, and the filtrate can be used for the next material separation water or reaction water.
The invention also provides N-cyanoethyl-N-benzylaniline which is prepared according to the preparation method. The N-cyanoethyl-N-benzylaniline has low content of chlorinated benzene and chlorinated toluene, and is convenient for producing dyes.
Specifically, in the N-cyanoethyl-N-benzylaniline of the present invention, the sum of the contents of monochlorobenzene and dichlorotoluene may be 50ppm or less, preferably 20ppm or less, more preferably 10ppm or less, so that the contents of chlorobenzene and chlorotoluene on the dyed fabric of the dye synthesized from the intermediate N-cyanoethyl-N-benzylaniline do not exceed the limit requirements of Oeko-tex standard 100. The N-cyanoethyl-N-benzylaniline of the invention can not contain chlorobenzene, other chlorobenzene and toluene chloride compounds.
The invention also provides the application of the N-cyanoethyl-N-benzylaniline prepared by the preparation method or the N-cyanoethyl-N-benzylaniline prepared by the preparation method in preparing dye. For example: the N-cyanoethyl-N-benzylaniline can be used for synthesizing SE type (medium temperature type) disperse dye, has higher color fixation rate and sublimation resistance fastness, is suitable for dyeing polyester fibers by a hot melt method, and has better dyeing effect by a high-temperature high-pressure method.
Examples
Embodiments of the present invention will be described in detail below with reference to examples, but those skilled in the art will appreciate that the following examples are only illustrative of the present invention and should not be construed as limiting the scope of the present invention. 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.
Example 1
The reaction steps are as follows: 1300kg of bottom water, 2600kg of N-cyanoethylaniline, 950kg of soda ash and 2300kg of benzyl chloride are put into a 10000L glass-lined reaction kettle, the temperature is slowly raised to 105-110 ℃ within 16 hours after the feeding is finished, and then the reaction is carried out under the condition of heat preservation until the reaction is completed. Sampling and detecting to obtain qualified product, wherein the reaction is completed when the purity (HPLC) of the raw material N-cyanoethylaniline is less than or equal to 3%.
Standing: after the reaction is finished, controlling the temperature of the reaction kettle to be 100 ℃, slowly adding 1700kg of water into the reaction kettle, continuously stirring for 1 hour after the water is added, standing for 1 hour, layering, firstly removing a lower water layer, and then conveying an upper layer to an evaporation kettle.
A distillation step: and (3) heating the evaporation kettle to 120 ℃ by using jacket steam, starting straight-through steam to perform reduced pressure distillation after the distillate quantity of the fraction is reduced, stopping distillation when the distillate quantity of the fraction reaches 1000kg (the contents of continuous benzene chloride and toluene chloride in the fraction are not changed basically), and removing the fraction to obtain a distillation product.
A precipitation step: 6000kg of bottom water is put into the material separating kettle, then the distillation product in the evaporation kettle is conveyed to the material separating kettle, so that the temperature of the distillation product is reduced to 55 ℃, material separation is carried out, the material separation is finished, N-cyanoethyl-N-benzylaniline is obtained through centrifugation, and the obtained filtrate can be used for next batch of water for separation or reaction.
Example 2
The reaction steps are as follows: 2600kg of separated material filtrate, 2600kg of N-cyanoethylaniline, 950kg of soda ash and 2400kg of benzyl chloride are put into a 10000L glass-lined reaction kettle, the temperature is slowly raised to 105-110 ℃ within 12 hours after the materials are put into the reaction kettle, and then the reaction is carried out under the condition of heat preservation until the reaction is completed. Sampling and detecting to obtain qualified product, wherein the reaction is completed when the purity (HPLC) of the raw material N-cyanoethylaniline is less than or equal to 3%.
Standing: after the reaction is finished, controlling the temperature of the reaction kettle to be 100 ℃, slowly adding 2600kg of water into the reaction kettle, continuously stirring for 1 hour after the addition is finished, standing for 1 hour, layering, firstly removing a lower water layer, and then conveying an upper layer to an evaporation kettle.
A distillation step: and (3) heating the evaporation kettle to 130 ℃ by using jacket steam, starting straight-through steam to carry out atmospheric distillation after the distillate quantity of the fraction is reduced, stopping distillation when the distillate quantity of the fraction reaches 800kg (the contents of continuous benzene chloride and toluene chloride in the fraction are not changed basically), and removing the fraction to obtain a distillation product.
A precipitation step: 6000kg of bottom water is put into the material separating kettle, then the distillation product in the evaporation kettle is conveyed to the material separating kettle, so that the temperature of the distillation product is reduced to 55 ℃, material separation is carried out, the material separation is finished, N-cyanoethyl-N-benzylaniline is obtained through centrifugation, and the obtained filtrate can be used for next batch of water for separation or reaction.
Comparative example 1
The reaction steps are as follows: 2600kg of bottom water, 2600kg of N-cyanoethylaniline, 950kg of soda ash and 2300kg of benzyl chloride are put into a 10000L glass-lined reaction kettle, the temperature is slowly raised to 105-110 ℃ within 16 hours after the putting is finished, and then the reaction is carried out under the condition of heat preservation until the reaction is completed. Sampling and detecting to obtain qualified product, wherein when the purity (HPLC) of the raw material N-cyanoethylaniline is less than or equal to 3%, the reaction is complete;
a precipitation step: after the reaction is finished, 3400kg of water is slowly added into the kettle, the temperature is continuously reduced to below 50 ℃ after the addition is finished, the material is separated out, the N-cyanoethyl-N-benzylaniline is obtained by centrifugation after the material separation is finished, and the obtained filtrate can be used for next separation water or reaction water.
Comparative example 2
The reaction steps are as follows: 1300kg of bottom water, 2600kg of N-cyanoethylaniline, 950kg of soda ash and 2300kg of benzyl chloride are put into a 10000L glass-lined reaction kettle, the temperature is slowly raised to 105-110 ℃ within 15 hours after the feeding is finished, and then the reaction is carried out under the condition of heat preservation until the reaction is completed. Sampling and detecting to obtain qualified product, wherein the reaction is completed when the purity (HPLC) of the raw material N-cyanoethylaniline is less than or equal to 3%.
A distillation step: and after the reaction is finished, transferring all the materials to an evaporation kettle, directly starting straight-through steam to carry out normal pressure distillation until the distillate quantity of the distillate reaches 1000kg, stopping distillation, and removing the distillate to obtain a distillation product.
A precipitation step: and after distillation, transferring the material to a material separating kettle, adding 6000kg of bottom water into the material separating kettle, conveying the distillation product in the evaporation kettle to the material separating kettle to cool the distillation product to 55 ℃, separating the material, and after the material separation is finished, centrifuging to obtain the N-cyanoethyl-N-benzylaniline, wherein the obtained filtrate can be used for next batch of separation water or reaction water.
Performance testing
The contents of chlorobenzene and toluene chloride in examples 1-2 and comparative examples 1-2 of the present invention were measured according to the method of GB/T20384-2006 "determination of residual amounts of chlorobenzene and toluene chloride for textiles", and the results are shown in Table 1 below.
TABLE 1
| Example 1 | Example 2 | Comparative example 1 | Comparative example 2 | |
| Monochlorobenzene content/ppm | Is free of | 6.78 | 273.72 | 237.04 |
| Dichlorotoluene content/ppm | Is free of | Is free of | 8.21 | 2.46 |
| Chlorinated benzene content/ppm | Is free of | Is free of | Is free of | Is free of |
As can be seen from Table 1, the eco-friendly N-cyanoethyl-N-benzylaniline prepared by the method of example 1-2 contains no monochlorobenzene and dichlorotoluene or has a very low content, so that the purity of the eco-friendly N-cyanoethyl-N-benzylaniline is higher, and the content of monochlorobenzene and dichlorotoluene on the fabric dyed by the dye synthesized from the intermediate does not exceed the limit requirement of Oeko-TexStandard 100. In addition, the N-cyanoethyl-N-benzylaniline prepared by the method does not contain other chlorobenzene and chlorotoluene compounds.
The preparation method of comparative example 1, which did not include the standing step and the distillation step, produced N-cyanoethyl-N-benzylaniline having high contents of monochlorobenzene and dichlorotoluene and low purity of N-cyanoethyl-N-benzylaniline.
The preparation method of comparative example 2, which did not include the standing step, produced N-cyanoethyl-N-benzylaniline having high contents of monochlorobenzene and dichlorotoluene and low purity.
The above examples of the present invention are merely examples for clearly illustrating the present invention and are not intended to limit the embodiments of the present invention. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. Any modification, equivalent replacement, and improvement made within the spirit and principle of the present invention should be included in the protection scope of the claims of the present invention.
Claims (10)
1. A preparation method of N-cyanoethyl-N-benzylaniline is characterized by comprising the following steps:
the reaction steps are as follows: adding water, cyanoethylaniline, benzyl chloride and sodium carbonate into a reaction kettle for reaction to obtain a reaction product;
standing: continuously adding water into the reaction kettle, uniformly mixing, standing and layering to obtain a water phase and an organic phase;
a distillation step: and distilling the organic phase, and removing fractions to obtain a distillation product.
2. The preparation method according to claim 1, wherein in the reaction step, the water is added in an amount of 50 to 100% by weight based on the weight of the cyanoethylaniline; the mol ratio of the N-cyanoethylaniline to the benzyl chloride to the sodium carbonate is 1: 1.0-1.1: 0.5 to 0.6.
3. The method according to claim 1 or 2, wherein the water is added in an amount of 50 to 150% by weight based on the weight of N-cyanoethylaniline in the step of standing.
4. The production method according to any one of claims 1 to 3, wherein the distillation step comprises: starting jacket steam, heating to 100-160 ℃, and then starting straight-through steam for distillation; preferably, the distillation comprises atmospheric distillation or vacuum distillation.
5. The method according to any one of claims 1 to 4, wherein the reaction temperature in the reaction step is 90 ℃ to 120 ℃, preferably 100 ℃ to 110 ℃.
6. The method according to any one of claims 1 to 5, wherein in the standing step, the temperature of the reaction vessel is controlled to be between 90 ℃ and 110 ℃, preferably between 95 ℃ and 105 ℃.
7. The production method according to any one of claims 1 to 6, characterized by further comprising:
a precipitation step: adding water into the distillation product, and cooling the distillation product to separate out the N-cyanoethyl-N-benzylaniline.
8. N-cyanoethyl-N-benzylaniline, prepared according to the preparation process of any one of claims 1 to 7.
9. The cyanoethyl-N-benzylaniline according to claim 8, wherein the sum of the contents of monochlorotoluene and dichlorotoluene in the cyanoethyl-N-benzylaniline is 50ppm or less, preferably 20ppm or less, more preferably 10ppm or less.
10. Use of the cyanoethyl-N-benzylaniline prepared according to the process of any one of claims 1 to 7 or according to claim 8 or 9 for the preparation of dyes.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113527909A (en) * | 2021-07-23 | 2021-10-22 | 杭州吉华江东化工有限公司 | Synthesis process of environment-friendly dye |
| CN115536548A (en) * | 2022-10-10 | 2022-12-30 | 浙江亿得新材料股份有限公司 | Environment-friendly intermediate synthesis method |
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| CN113527909A (en) * | 2021-07-23 | 2021-10-22 | 杭州吉华江东化工有限公司 | Synthesis process of environment-friendly dye |
| CN115536548A (en) * | 2022-10-10 | 2022-12-30 | 浙江亿得新材料股份有限公司 | Environment-friendly intermediate synthesis method |
| CN115536548B (en) * | 2022-10-10 | 2023-09-12 | 浙江亿得新材料股份有限公司 | Environment-friendly synthesis method of intermediate |
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