CN115784944A - Synthesis method of high-purity environment-friendly acid dye intermediate - Google Patents
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Abstract
The invention relates to a synthesis method of an intermediate of a high-purity environment-friendly acid dye, which comprises the following steps: mixing aniline, sodium metabisulfite and formaldehyde with water, adjusting the mixture to a set pH value, and carrying out addition reaction at a first temperature for a first time to obtain a first solution; cooling the solution I to a temperature II, adding a sodium chloride solution, and crystallizing to separate sodium anilinesulfonate out; mixing sodium benzene sulfamate with water, adding p-aminobenzene sulfonic acid, and performing coupling reaction at the second temperature for the second time to obtain a second solution; adding a sodium chloride solution into the solution II, and crystallizing to separate out a solid I; mixing the solid I with water, adding liquid alkali, and performing hydrolysis reaction at the temperature III for the time III to obtain a solution III; and cooling the solution III to the temperature IV, adding a sodium chloride solution, and crystallizing to separate out the p-aminoazobenzene-4-sulfonic acid. The method improves the purity of the generated sodium phenylamino sulfonate, reduces the content of byproducts, reduces the cost of aniline boiling water treatment, and simultaneously reduces the residual quantity of aniline.
Description
Technical Field
The invention belongs to the technical field of dye preparation, and particularly relates to a synthesis method of an intermediate of a high-purity environment-friendly acid dye.
Background
With the global environmental protection and the promotion of human health consciousness, besides 24 harmful azo dyes forbidden by textile and leather dyes, aniline is classified as a harmful substance to human bodies, and more manufacturers in recent years require that the dyes for textile and leather cannot have aniline residues, so that how to reduce aniline residues and emission in the production of aniline-related intermediates or dyes is of great importance to the dye industry.
The p-aminoazobenzene-4-sulfonic acid is an important intermediate for preparing acid red and direct red dyes, and the synthesis process is synthesized by aniline, sodium metabisulfite, formaldehyde and sodium sulfanilate.
According to the method, the reaction condition of the aminoazobenzene-4-sulfonic acid is corrected, the purity change of the aniline, the product and the by-product is detected by using HPLC (high performance liquid chromatography), the optimal condition is optimized, the aniline residue is reduced to the minimum, and the product purity reaches the maximum.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention aims to provide a method for synthesizing an intermediate of a high-purity environment-friendly acid dye, and aims to solve the problems that in the prior art, the traditional synthesis process method is adopted, the aniline residue is more, the waste water is easy to remain too much, the yield of the intermediate after synthesis is low, and the color light of the prepared red dye is even influenced; the traditional synthesis process is optimized, and the aniline residue is reduced, so that the purity of the main product reaches the highest.
The purpose of the invention is realized by the following technical scheme:
a synthetic method of an intermediate of a high-purity environment-friendly acid dye comprises the following steps:
mixing aniline, sodium metabisulfite and formaldehyde with water, adjusting the pH value to a set pH value by using liquid alkali or hydrochloric acid, and carrying out addition reaction to obtain a solution I;
adding a sodium chloride solution into the first solution, and crystallizing to separate out sodium benzenesulfonate;
mixing sodium benzene sulfamate with water, adding p-aminobenzenesulfonic acid, and performing coupling reaction to obtain a solution II;
adding a sodium chloride solution into the solution II, and crystallizing to separate out a solid I;
mixing the solid I with water, adding liquid alkali, and performing hydrolysis reaction to obtain a solution III;
and adding a sodium chloride solution into the solution III, and crystallizing to separate out p-aminoazobenzene-4-sulfonic acid.
The sodium anilinesulfonate synthesized by the method has high purity, low content of byproducts and low aniline residue, and the finally generated p-aminoazobenzene-4-sulfonic acid has the purity of more than 99 percent and the byproduct of less than 1 percent and has no aniline residue by utilizing the synthesis process.
In order to optimize the technical scheme, the specific measures adopted further comprise:
furthermore, the molar ratio of the aniline to the sodium metabisulfite to the formaldehyde is 1 (0.5-0.6) to 1-1.3, and the pH value is 2-9.5.
Further, the temperature of the addition reaction is 40-70 ℃, and the time of the addition reaction is 1-3 h.
Further, before adding the sodium chloride solution into the first solution, the method further comprises the following steps: the solution was cooled to 40-50 ℃.
Further, the volume fraction of the sodium chloride solution is 10-20%.
Further, the molar ratio of the sodium benzene sulfamic acid to the p-aminobenzenesulfonic acid is 1:0.8-1.0.
Further, the temperature of the coupling reaction is 10-20 ℃, and the time of the coupling reaction is 2-4 h.
Further, the volume fraction of the liquid alkali is 20-30%.
Further, the temperature of the hydrolysis reaction is 95-100 ℃, and the time of the hydrolysis reaction is 2-5 h.
Further, before adding the sodium chloride solution into the solution III, the method further comprises the following steps: cooling the solution III to below 70 ℃.
The invention has the beneficial effects that:
the method is characterized in that aniline, sodium pyrosulfite and formaldehyde are subjected to addition reaction, and the reaction time, temperature and pH value are optimized, so that the purity of the generated p-aminoazobenzene-4-sulfonic acid precursor (sodium anilinesulfonate) is improved, the content of byproducts is reduced, the cost of aniline boiling water treatment is reduced, and the aniline residual quantity is reduced.
Compared with the traditional method for synthesizing sodium phenylaminosulfonate, the method has the advantages that the aniline reaction is completed at a higher temperature of 60-70 ℃ for a prolonged time by increasing the proportion of formaldehyde, but the synthesis method is lower in yield, and the p-aminoazobenzene-4-sulfonic acid intermediate obtained after the precursor and p-aminobenzenesulfonic acid are subjected to coupling reaction is lower in yield and reddish in color. The purity of the traditional synthetic sodium anilinesulfonate is analyzed by HPLC detection, the proportion of benzaldehyde by-product is 6-12%, and the proportion of the by-product is increased along with the temperature rise and the time extension, so that the yield and the color of the final p-aminoazobenzene-4-sulfonic acid intermediate can cause the color light of the acid red dye prepared subsequently to be dark and reduced. Therefore, the preparation method disclosed by the invention optimizes and sets the reaction time, the temperature and the pH value of the sodium anilinesulfonate, can effectively save energy and time, reduces the cost of aniline wastewater treatment, and improves the yield and the quality of products.
Detailed Description
The present invention will be further described with reference to the following examples for facilitating understanding of those skilled in the art, and the description of the embodiments is not intended to limit the present invention.
A synthesis method of an intermediate of a high-purity environment-friendly acid dye comprises two parts, namely, firstly preparing a precursor of p-aminoazobenzene-4-sulfonic acid, and then preparing p-aminoazobenzene-4-sulfonic acid.
A synthetic method of an intermediate of a high-purity environment-friendly acid dye comprises the following steps:
preparing a precursor: mixing aniline, sodium metabisulfite and formaldehyde with water, adjusting the pH value to be the pH value by using liquid alkali or hydrochloric acid, and carrying out addition reaction at a first temperature for a first time to obtain a first solution; and cooling the solution I to the temperature II, adding a sodium chloride solution, and crystallizing to separate out the sodium phenylamino sulfonate.
Preparation of p-aminoazobenzene-4-sulfonic acid: mixing sodium benzene sulfamate with water, adding p-aminobenzenesulfonic acid, and performing coupling reaction at the second temperature for the second time to obtain a second solution; adding a sodium chloride solution into the solution II, and crystallizing to separate out a solid I; mixing the solid I with water, adding liquid alkali, and performing hydrolysis reaction at the temperature III for the time III to obtain a solution III; and cooling the solution III to the temperature IV, adding a sodium chloride solution, and crystallizing to separate out the p-aminoazobenzene-4-sulfonic acid.
In the process of synthesizing the p-aminoazobenzene-4-sulfonic acid intermediate, the synthesis of a precursor sodium anilinesulfonate is crucial, and the purity of the precursor sodium anilinesulfonate can greatly influence the purity of the finally synthesized p-aminoazobenzene-4-sulfonic acid intermediate, so that the following embodiment is obtained by analyzing the precursor, then the optimal synthesis method is selected to synthesize the precursor, and then the p-aminoazobenzene-4-sulfonic acid is synthesized.
Preparing a precursor: example 1
Adding 200mL of water into a 1000mL four-mouth bottle, adding a sodium metabisulfite solution with the concentration of 0.55mol/L, stirring until the sodium metabisulfite solution is dissolved, adding a formaldehyde solution with the concentration of 1.05mol/L, adding an aniline solution with the concentration of 1.0mol/L, adjusting the pH of the reaction to be 5.5, and performing an addition reaction at 70 ℃ for 1 hour to obtain a solution I; wherein, the mol ratio of aniline, sodium metabisulfite and formaldehyde is 1.55. And cooling the solution I to 40 ℃, adding a sodium chloride solution with the volume fraction of 20%, crystallizing, separating out, and performing pressure filtration to obtain the sodium anilinesulfonate. After the reaction is finished, the purity of the main product, the by-product and aniline in the solution one is detected by using HPLC, wherein the main product is sodium anilinesulfonate (the purity is 90.44%), the by-product is 6.58% benzaldehyde, and the residual quantity of aniline is 2.98%.
Preparing a precursor: example 2
Adding 200mL of water into a 1000mL four-mouth bottle, adding a sodium metabisulfite solution with the concentration of 0.55mol/L, stirring until the sodium metabisulfite solution is dissolved, adding a formaldehyde solution with the concentration of 1.05mol/L, adding an aniline solution with the concentration of 1.0mol/L, adjusting the pH of the reaction to be 5.5, and performing addition reaction for 3 hours at 70 ℃ to obtain a solution I; wherein the molar ratio of aniline, sodium metabisulfite and formaldehyde is 1.55. And cooling the solution I to 40 ℃, adding a sodium chloride solution with the volume fraction of 20%, crystallizing, separating out, and performing pressure filtration to obtain the sodium benzenesulfonate. After the reaction is finished, the purity of the main product, the by-product and the aniline in the solution one are detected by using HPLC, wherein the main product is sodium anilinesulfonate (the purity is 87.32%), the by-product is 11.63% benzaldehyde, and the residual quantity of the aniline is 1.05%.
Preparing a precursor: example 3
Adding 200mL of water into a 1000mL four-mouth bottle, adding a sodium metabisulfite solution with the concentration of 0.55mol/L, stirring until the sodium metabisulfite solution is dissolved, adding a formaldehyde solution with the concentration of 1.05mol/L, adding an aniline solution with the concentration of 1.0mol/L, adjusting the pH of the reaction to be 2.5, and carrying out an addition reaction at 55 ℃ for 1h to obtain a solution I; wherein the molar ratio of aniline, sodium metabisulfite and formaldehyde is 1.55. And cooling the solution I to 40 ℃, adding a sodium chloride solution with the volume fraction of 20%, crystallizing, separating out, and performing pressure filtration to obtain the sodium benzenesulfonate. After the reaction is finished, the purity of the main product, the by-product and the aniline in the solution one are detected by using HPLC, wherein the main product is sodium anilinesulfonate (the purity is 87.58%), the by-product is 8.65% of benzaldehyde, and the residual amount of the aniline is 3.77%.
Preparing a precursor: example 4
Adding 200mL of water into a 1000mL four-mouth bottle, adding a sodium metabisulfite solution with the concentration of 0.55mol/L, stirring until the sodium metabisulfite solution is dissolved, adding a formaldehyde solution with the concentration of 1.05mol/L, adding an aniline solution with the concentration of 1.0mol/L, adjusting the pH of the reaction to be 2.5, and performing addition reaction for 3 hours at 55 ℃ to obtain a solution I; wherein, the mol ratio of aniline, sodium metabisulfite and formaldehyde is 1.55. And cooling the solution I to 40 ℃, adding a sodium chloride solution with the volume fraction of 20%, crystallizing, separating out, and performing pressure filtration to obtain the sodium benzenesulfonate. After the reaction is finished, the purity of the main product, the by-product and the aniline in the solution one are detected by using HPLC, wherein the main product is sodium anilinesulfonate (the purity is 66.17%), the by-product is 31.75% benzaldehyde, and the residual quantity of the aniline is 2.08%.
Preparing a precursor: example 5
Adding 200mL of water into a 1000mL four-mouth bottle, adding a sodium metabisulfite solution with the concentration of 0.55mol/L, stirring until the sodium metabisulfite solution is dissolved, adding a formaldehyde solution with the concentration of 1.05mol/L, adding an aniline solution with the concentration of 1.0mol/L, adjusting the pH of the reaction to be 9.5, and carrying out addition reaction for 1h at 55 ℃ to obtain a solution I; wherein the molar ratio of aniline, sodium metabisulfite and formaldehyde is 1.55. And cooling the solution I to 40 ℃, adding a sodium chloride solution with the volume fraction of 20%, crystallizing, separating out, and performing pressure filtration to obtain the sodium benzenesulfonate. After the reaction, the purity of the main product, the by-product and aniline in the first solution was measured by HPLC, wherein the main product was sodium benzenesulfonate (purity of 97.04%), the by-product was 1.62% benzaldehyde, and the residual amount of aniline was 1.34%.
Preparing a precursor: example 6
Adding 200mL of water into a 1000mL four-mouth bottle, adding a sodium metabisulfite solution with the concentration of 0.55mol/L, stirring until the sodium metabisulfite solution is dissolved, adding a formaldehyde solution with the concentration of 1.05mol/L, adding an aniline solution with the concentration of 1.0mol/L, adjusting the pH of the reaction to be 9.5, and performing addition reaction for 3 hours at 55 ℃ to obtain a solution I; wherein the molar ratio of aniline, sodium metabisulfite and formaldehyde is 1.55. And cooling the solution I to 40 ℃, adding a sodium chloride solution with the volume fraction of 20%, crystallizing, separating out, and performing pressure filtration to obtain the sodium benzenesulfonate. After the reaction is finished, the purity of the main product, the by-product and the aniline in the solution I is detected by using HPLC, wherein the main product is sodium anilinesulfonate (the purity is 94.42%), the by-product is 5.10% benzaldehyde, and the residual amount of the aniline is 0.48%.
Preparing a precursor: example 7
Adding 200mL of water into a 1000mL four-mouth bottle, adding a sodium metabisulfite solution with the concentration of 0.55mol/L, stirring until the sodium metabisulfite solution is dissolved, adding a formaldehyde solution with the concentration of 1.05mol/L, adding an aniline solution with the concentration of 1.0mol/L, adjusting the pH of the reaction to be 9.5, and carrying out addition reaction for 1h at 40 ℃ to obtain a solution I; wherein, the mol ratio of aniline, sodium metabisulfite and formaldehyde is 1.55. And cooling the solution I to 40 ℃, adding a sodium chloride solution with the volume fraction of 20%, crystallizing, separating out, and performing pressure filtration to obtain the sodium anilinesulfonate. After the reaction is finished, the purity of the main product, the by-product and the aniline in the solution I is detected by using HPLC, wherein the main product is sodium anilinesulfonate (the purity is 97.71%), the by-product is 1.16% benzaldehyde, and the residual amount of the aniline is 1.68%.
Preparing a precursor: example 8
Adding 200mL of water into a 1000mL four-mouth bottle, adding a sodium metabisulfite solution with the concentration of 0.55mol/L, stirring until the sodium metabisulfite solution is dissolved, adding a formaldehyde solution with the concentration of 1.05mol/L, adding an aniline solution with the concentration of 1.0mol/L, adjusting the pH of the reaction to be 9.5, and carrying out addition reaction for 3 hours at 40 ℃ to obtain a solution I; wherein, the mol ratio of aniline, sodium metabisulfite and formaldehyde is 1.55. And cooling the solution I to 40 ℃, adding a sodium chloride solution with the volume fraction of 20%, crystallizing, separating out, and performing pressure filtration to obtain the sodium anilinesulfonate. After the reaction, the purity of the main product, the by-product and aniline in the first solution was measured by HPLC, wherein the main product was sodium benzenesulfonate (purity of 97.71%), the by-product was 1.63% benzaldehyde, and the residual amount of aniline was 0.66%.
Preparing a precursor: example 9
Adding 200mL of water into a 1000mL four-mouth bottle, adding a sodium metabisulfite solution with the concentration of 0.55mol/L, stirring until the sodium metabisulfite solution is dissolved, adding a formaldehyde solution with the concentration of 1.05mol/L, adding an aniline solution with the concentration of 1.0mol/L, adjusting the pH of the reaction to be 9.5, and carrying out an addition reaction for 5 hours at 40 ℃ to obtain a solution I; wherein the molar ratio of aniline, sodium metabisulfite and formaldehyde is 1.55. And cooling the solution I to 40 ℃, adding a sodium chloride solution with the volume fraction of 20%, crystallizing, separating out, and performing pressure filtration to obtain the sodium anilinesulfonate. After the reaction is finished, the purity of the main product, the by-product and the aniline in the solution I is detected by using HPLC, wherein the main product is sodium anilinesulfonate (the purity is 97.54%), the by-product is 2.10% benzaldehyde, and the residual amount of the aniline is 0.36%.
Combining examples 1-9 and table 1, the reaction process flow in examples 1 and 2 can effectively reduce the residual concentration of aniline, but the by-products are increased, resulting in a decrease in the purity of the main product. In the reaction process flows of comparative examples 3 and 4, under the relatively strong acidic condition and the prolonged reaction time, part of the main product is decomposed into byproducts, so that the purity of the byproducts is greatly increased to 31.75 percent, and the purity of the main product is reduced to 66.17 percent. Examples 5 and 6, under the strongly acidic condition, the aniline addition reaction is promoted to prepare sodium anilinesulfonate, so that the purity of the main product is improved from 90.44% to 97.04%, the aniline residual quantity is 2.98% -1.34%, and meanwhile, the aniline residual quantity is reduced along with the prolonging of the reaction time, but the proportion of the by-products is increased more. In comparative examples 7-9, under the conditions of stronger alkalinity and lower temperature, the purity of the main product can be higher than 97 percent along with the extension of the reaction time, the residual quantity of the aniline is reduced to be minimum 0.36 percent, and the by-product is only slightly improved by 0.5 percent. As the temperature is lowered, the rate of decomposition of the main product into by-products is lowered, and the reaction of the residual aniline is continued slowly, but aniline remains.
Preparation of p-aminoazobenzene-4-sulfonic acid: 900ml of the sodium benzenesulfonate produced in examples 7 to 9 was mixed with water and dissolved in a 2000ml beaker, and a p-aminobenzenesulfonic acid solution having a concentration of 0.9mol/L was added to conduct a coupling reaction at 15 ℃ for 3 hours to obtain a second solution; wherein the molar ratio of the sodium benzene-amino sulfonate to the p-aminobenzenesulfonic acid is 1:0.9. adding a sodium chloride solution with the volume fraction of 20% into the second solution, crystallizing to separate out a first solid, mixing the first solid with water, adding liquid caustic soda with the volume fraction of 25%, heating to 97 ℃, performing hydrolysis reaction for 3.5 hours to obtain a third solution, cooling the third solution to below 70 ℃, adding a sodium chloride solution with the volume fraction of 20%, crystallizing to separate out, and performing filter pressing to obtain the p-aminoazobenzene-4-sulfonic acid. And (3) detecting the purity of the main product, the by-product and the aniline in the solution III by using HPLC after the reaction is finished, wherein the main product is p-aminoazobenzene-4-sulfonic acid (the concentration is more than 99 percent), the by-product is a benzaldehyde substance (the content is less than 1 percent), and no aniline residue exists.
In the existing method for synthesizing sodium benzenesulfonamide, as shown in example 1-2, the purity is 87-90%, the byproduct benzaldehyde is 6-12%, and aniline remains 1-3%, although the purity is nearly 90%, the final intermediate prepared from the acidic red dye has poor color stability due to the byproduct benzaldehyde being left in a high proportion, and the aniline remains improve the current environmental protection and human health consciousness, so that the aniline remains in the intermediate, dye and wastewater are reduced to the minimum. The invention optimizes each key reaction condition, which can save energy and time, reduce the cost of aniline wastewater treatment, and improve the yield and quality of the product.
Therefore, compared with the prior art, the treatment process can completely remove the residual aniline, the purity of the obtained aminoazobenzene-4-sulfonic acid can exceed 99%, and the concentration of the by-product is less than 1%.
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Experimental data analysis table
The above is only a preferred embodiment of the present invention, and the protection scope of the present invention is not limited to the above-mentioned embodiments, and all technical solutions belonging to the idea of the present invention belong to the protection scope of the present invention. It should be noted that modifications and adaptations to those skilled in the art without departing from the principles of the present invention may be apparent to those skilled in the relevant art and are intended to be within the scope of the present invention.
Claims (10)
1. A synthetic method of an intermediate of a high-purity environment-friendly acid dye is characterized by comprising the following steps:
mixing aniline, sodium metabisulfite and formaldehyde with water, adjusting the pH value to a set value, and carrying out addition reaction to obtain a solution I;
adding a sodium chloride solution into the first solution, and crystallizing to separate out sodium phenylamino sulfonate;
mixing sodium benzene sulfamate with water, adding p-aminobenzenesulfonic acid, and performing coupling reaction to obtain a solution II;
adding a sodium chloride solution into the solution II, and crystallizing to separate out a solid I;
mixing the solid I with water, adding liquid alkali, and performing hydrolysis reaction to obtain a solution III;
and adding a sodium chloride solution into the solution III, and crystallizing to separate out p-aminoazobenzene-4-sulfonic acid.
2. The method for synthesizing the intermediate of the high-purity environment-friendly acid dye according to claim 1, wherein the method comprises the following steps: the molar ratio of the aniline to the sodium metabisulfite to the formaldehyde is 1 (0.5-0.6) to 1-1.2, and the pH value is 2-9.5.
3. The method for synthesizing the intermediate of the high-purity environment-friendly acid dye according to claim 1, wherein the method comprises the following steps: the temperature of the addition reaction is 40-70 ℃, and the time of the addition reaction is 1-3 h.
4. The method for synthesizing the intermediate of the high-purity environment-friendly acid dye according to claim 1, wherein before the step of adding the sodium chloride solution into the first solution, the method further comprises the following steps: the solution was cooled to 40-50 ℃.
5. The method for synthesizing the intermediate of the high-purity environment-friendly acid dye according to claim 1, wherein the method comprises the following steps: the volume fraction of the sodium chloride solution is 10-20%.
6. The method for synthesizing the intermediate of the high-purity environment-friendly acid dye according to claim 1, wherein the method comprises the following steps: the molar ratio of the sodium benzene sulfamic acid to the p-aminobenzenesulfonic acid is 1:0.8-1.0.
7. The method for synthesizing the intermediate of the high-purity environment-friendly acid dye according to claim 1, wherein the method comprises the following steps: the temperature of the coupling reaction is 10-20 ℃, and the time of the coupling reaction is 2-4 h.
8. The method for synthesizing the intermediate of the high-purity environment-friendly acid dye according to claim 1, wherein the method comprises the following steps: the volume fraction of the liquid caustic soda is 20-30%.
9. The method for synthesizing the intermediate of the high-purity environment-friendly acid dye according to claim 1, wherein the method comprises the following steps: the temperature of the hydrolysis reaction is 95-100 ℃, and the time of the hydrolysis reaction is 2-5 h.
10. The method for synthesizing the intermediate of the high-purity environment-friendly acid dye according to claim 6, wherein before the step of adding the sodium chloride solution into the solution III, the method further comprises the following steps: cooling the third solution to below 70 ℃.
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