A preparation method of N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide

Abstract

The present invention relates to a preparation method of N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide, and belongs to the technical field of solvent dye synthesis methods. The present invention comprises the following steps: 1,4-dihydroxyanthraquinone, 1,4-dihydroxyanthraquinone leuco body, p-phenylenediamine, resin acid catalyst, organic acid and solvent are subjected to temperature reaction, filtered and the solvent is removed by distillation; dilute alkali solution is continuously added, stirred at 70-90°C for 30-60 minutes, filtered, washed with water until neutral, dried to obtain a condensation material; acetic acid and acetic anhydride are added to the condensation material, the temperature reaction is performed, the mixture is cooled and filtered, washed until neutral, dried to obtain N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide; the N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide prepared by the present invention has high purity and yield.

Description

Technical Field

[0001] The invention relates to the technical field of solvent dye synthesis methods, in particular to a method for preparing N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide. Background Art

[0002] N-[4-[(4-Hydroxyanthraquinone-1-yl)amino]phenyl]acetamide, also known as Solvent Blue 122, is a deep red-blue solvent dye. It has good heat resistance and light resistance, good migration resistance and high tinting strength. It is mainly used in polyester fiber PET fiber, engineering plastics, and widely used in plastics such as PS, PET, PA, PC, ABS, etc.

[0003] Chinese patent CN104725253A: discloses a method for preparing solvent blue 122. Boric acid, p-aminoacetanilide, 1, 4-dihydroxyanthraquinone, 1, 4-dihydroxyanthraquinone leuco form are put into methanol, and kept warm at normal pressure. When the contents of 1, 4-dihydroxyanthraquinone and 1, 4-dihydroxyanthraquinone leuco form are both less than 3%, the reaction is terminated, and the temperature is lowered to room temperature for filtration, washing, and obtaining a crude product; the obtained crude product is stirred in an alkaline solution at 80-85°C for more than 0.5 hours, filtered while hot, washed to neutral, and then the obtained filter cake is stirred in an acid solution at 70-75°C, filtered while hot, washed to neutral, and dried to obtain the product.

[0004] Chinese patent CN108624078A: relates to a one-bath production method of solvent blue 122 dye, which comprises the following steps: (a) adding n-butanol, p-nitroaniline, 1,4-dihydroxyanthraquinone, zinc powder and an auxiliary agent into a reaction container, stirring and dissolving to obtain a first mixture; the auxiliary agent is a mixture composed of one or more selected from acetic acid, sulfuric acid and hydrochloric acid; (b) heating the first mixture to 80-150°C to react to an end point, and adding acetic anhydride after cooling to carry out an acylation reaction; (c) washing the filter cake with n-butanol, and collecting the washing liquid and the filtrate.

[0005] Chinese patent CN109810012B: discloses a method for preparing anhydrous solvent blue 122. 1,4-dihydroxyanthraquinone, p-aminoacetanilide, leuco form of 1,4-dihydroxyanthraquinone, boric acid, and organic acid are put into a mixed solution of DMF and isobutyl alcohol, refluxed and kept warm at normal pressure, and reacted until the product content is greater than 97%, and the contents of leuco form of 1,4-dihydroxyanthraquinone and 1,4-dihydroxyanthraquinone are both less than 1%, filtered while hot, the mother liquor is cooled to precipitate the dye, filtered, drained, and then pulped with methanol, filtered, washed with methanol, and the filter cake is vacuum dried to recover methanol to obtain the product.

[0006] The N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide prepared by the above patents and prior art has high production cost and low product purity. Summary of the invention

[0007] In order to solve the above problems, the present invention provides a method for preparing N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide, and the operating steps are as follows: S1: Weigh 32-48 parts of 1,4-dihydroxyanthraquinone, 10-18 parts of leuco form of 1,4-dihydroxyanthraquinone, 40-55 parts of p-phenylenediamine, 5-10 parts of resin acid catalyst, 1-3 parts of organic acid, and 300-500 parts of solvent by weight, and heat to react; S2: After the reaction is completed, filter and distill to remove the solvent; S3: Continue to add dilute alkali solution, stir at 70-90°C for 30-60 minutes, filter, wash with water until neutral, and dry to obtain a condensation material; S4: Add 100-200 parts of acetic acid and 62-96 parts of acetic anhydride to the condensation material, heat the reaction, cool and filter, wash to neutrality, and dry to obtain N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide.

[0008] The organic acid is one of oxalic acid, malonic acid, formic acid, propionic acid and acetic acid.

[0009] The solvent is one of DMF, methanol, n-butanol, isobutanol and butanol.

[0010] The reaction temperature of S1 is 70-100°C and the reaction time is 10-15 hours.

[0011] The reaction temperature of S4 is 100-110° C. and the reaction time is 100-150 minutes.

[0012] The preparation method of the resin acid catalyst is: H1: Preparation of Vinyl D006 Sodium Polystyrene Sulfonic Acid Resin by Acylation Add 100-130 parts of D006 sodium polystyrene sulfonic acid resin, 1000-1200 parts of ethylene sulfonyl chloride, and 7-14 parts of zinc chloride into the reaction device 1, and react at 20-30° C. for 10-20 hours; after the reaction is completed, filter and dry to obtain vinyl D006 sodium polystyrene sulfonic acid resin; H2: Mixed reactants Add 3-10 parts of 2,3-dimercaptosuccinic acid, 0.2-0.7 parts of 3-vinylquinoline (CAS No.: 67752-31-2), 1000-1300 parts of toluene, and 0.003-0.04 parts of photoinitiator to the sodium vinyl D006 polystyrene sulfonic acid resin obtained in H1, and stir at room temperature for 120-150 minutes; H3: Polymerization under UV irradiation Exposing the mixture to ultraviolet light for 20-50 minutes to initiate a thiol-olefin click chemistry reaction; H4: Transformation to hydrogen type: Pickling solution preparation: prepare 1N hydrochloric acid solution, Flow rate: In ion exchange columns, it should be controlled at 5-10 times the volume of resin processed per hour; Flow rate: Maintain the flow rate at 1-3L / min to ensure adequate contact and transformation; Transformation time: Keep stirring and maintain temperature for 2-4 hours, then let stand for 1-2 hours to complete the transformation; The resin was thoroughly washed with a large amount of deionized water until the pH value of the washing solution was close to neutral, thereby obtaining a resin catalyst.

[0013] The ultraviolet light parameters are: Light source type: Use medium pressure mercury lamp as UV light source; Wavelength range: The main wavelength is between 250-400nm; Irradiation distance: Keep the distance between the sample and the light source about 20cm; Irradiation time: usually 20-50 minutes, depending on the reaction progress.

[0014] Reaction mechanism 1. Thiol-vinyl click chemistry reaction: Under appropriate conditions (such as light or heating), the thiol group (-SH) in 2,3-dimercaptosuccinic acid is activated to generate thiolate radicals (RS·). These thiolate radicals undergo addition reactions with the vinyl groups (C=C) in the sodium vinyl D006 polystyrene sulfonic acid resin to form new carbon-sulfur bonds (CS). At the same time, the vinyl group in 3-vinylquinoline also undergoes a similar addition reaction with another thiol group in 2,3-dimercaptosuccinic acid, introducing a quinoline group into the resin structure.

[0015] 2. Grafting process: Through the above-mentioned click chemistry reaction, quinoline and succinic acid were successfully grafted onto the sulfonic acid resin to form a grafted sulfonic acid resin catalyst with specific catalytic function.

[0016] Technical Effects The present invention discloses a method for preparing N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide. Compared with the prior art, the present invention has the following significant effects: 1. Improve catalytic efficiency: Compared with traditional inorganic acid catalysts, the sulfonic acid resin catalyst grafted with quinoline and succinic acid can more effectively promote the condensation reaction between 1,4-dihydroxyanthraquinone, 1,4-dihydroxyanthraquinone leuco form and p-phenylenediamine. This catalyst can provide a more suitable reaction environment, reduce the reaction activation energy, and thus accelerate the reaction rate.

[0017] 2. Reduce side effects: Due to the specific structure and function of the sulfonic acid resin catalyst, it can inhibit unnecessary side reactions to a certain extent and improve the purity of the target product.

[0018] 3. Easy to separate and recycle: The sulfonic acid resin catalyst is solid and can be easily separated from the reaction mixture and can be recycled and reused by simple filtration and washing, thereby reducing production costs.

[0019] 4. Environmentally friendly: The use of sulfonic acid resin catalysts instead of inorganic acid catalysts reduces the generation of waste acid, reduces environmental pollution, and complies with the principles of green chemistry. DETAILED DESCRIPTION

[0020] In order to further explain the technical means and effects adopted by the present invention to achieve the predetermined invention purpose, the following is a detailed description in combination with embodiments and comparative examples: N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide was determined by liquid chromatography. The results are shown in Table 1.

[0021] Example 1 A method for preparing N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide, the operating steps of which are: S1: Weigh 32g 1,4-dihydroxyanthraquinone, 10g 1,4-dihydroxyanthraquinone leuco form, 40g p-phenylenediamine, 5g resin acid catalyst, 1g organic acid, and 300g solvent, and heat to react; S2: After the reaction is completed, filter and distill to remove the solvent; S3: Continue to add dilute alkali solution, stir at 70°C for 30 minutes, filter, wash with water until neutral, and dry to obtain a condensation material; S4: Add 100 g of acetic acid and 62 g of acetic anhydride to the condensation material, heat the reaction, filter, wash to neutrality, and dry to obtain N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide.

[0022] The organic acid is oxalic acid.

[0023] The solvent is DMF.

[0024] The reaction temperature of S1 is 70°C and the reaction time is 10 hours.

[0025] The reaction temperature of S4 is 100° C. and the reaction time is 100 minutes.

[0026] The preparation method of the resin acid catalyst is: H1: Preparation of Vinyl D006 Sodium Polystyrene Sulfonic Acid Resin by Acylation Add 100g of D006 sodium polystyrene sulfonic acid resin, 1000g of ethylene sulfonyl chloride and 7g of zinc chloride into the reaction kettle 1, and react at 20°C for 10 hours; after the reaction is completed, filter and dry to obtain vinyl D006 sodium polystyrene sulfonic acid resin; H2: Mixed reactants Add 3 g of 2,3-dimercaptosuccinic acid, 0.2 g of 3-vinylquinoline (CAS No.: 67752-31-2), 1000 g of toluene, and 0.003 g of a photoinitiator to the sodium vinyl D006 polystyrene sulfonic acid resin obtained in H1, and stir at room temperature for 120 minutes; H3: Polymerization under UV irradiation The mixture was exposed to UV light for 20 min to initiate the thiol-olefin click chemistry reaction; H4: Transformation to hydrogen type: Pickling solution preparation: prepare 1N hydrochloric acid solution, Flow rate: in ion exchange columns, controlled at 5 times the volume of resin processed per hour; Flow rate: Maintain the flow rate at 1L / min to ensure adequate contact and transformation; Transformation time: Keep stirring and maintain temperature for 2 hours, then let stand for 1 hour to complete the transformation; The resin was thoroughly washed with a large amount of deionized water until the pH value of the washing solution was close to neutral, thereby obtaining a resin catalyst.

[0027] The ultraviolet light parameters are: Light source type: Use medium pressure mercury lamp as UV light source; Wavelength range: The main wavelength is between 250nm; Irradiation distance: Keep the distance between the sample and the light source about 20cm; Irradiation time: depends on the reaction progress, usually 20 minutes.

[0028] Example 2 A method for preparing N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide, the operating steps of which are: S1: Weigh 38g 1,4-dihydroxyanthraquinone, 12g 1,4-dihydroxyanthraquinone leuco form, 45g p-phenylenediamine, 6g resin acid catalyst, 2g organic acid, and 350g solvent, and heat to react; S2: After the reaction is completed, filter and distill to remove the solvent; S3: Continue to add dilute alkali solution, stir at 75°C for 40 minutes, filter, wash with water until neutral, and dry to obtain a condensation material; S4: Add 140 g of acetic acid and 78 g of acetic anhydride to the condensation material, heat the reaction, filter, wash to neutrality, and dry to obtain N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide.

[0029] The organic acid is malonic acid.

[0030] The solvent is methanol.

[0031] The reaction temperature of S1 is 80°C and the reaction time is 12 hours.

[0032] The reaction temperature of S4 is 105°C and the reaction time is 110 minutes.

[0033] The preparation method of the resin acid catalyst is: H1: Preparation of Vinyl D006 Sodium Polystyrene Sulfonic Acid Resin by Acylation Add 110g of D006 sodium polystyrene sulfonic acid resin, 1050g of ethylene sulfonyl chloride and 9g of zinc chloride into reaction equipment 1, and react at 25°C for 14 hours; after the reaction is completed, filter and dry to obtain vinyl D006 sodium polystyrene sulfonic acid resin; H2: Mixed reactants Add 5 g of 2,3-dimercaptosuccinic acid, 0.4 g of 3-vinylquinoline (CAS No.: 67752-31-2), 1100 g of toluene, and 0.01 g of photoinitiator to the sodium vinyl D006 polystyrene sulfonic acid resin obtained in H1, and stir at room temperature for 130 minutes; H3: Polymerization under UV irradiation The mixture was exposed to UV light for 30 min to initiate the thiol-olefin click chemistry reaction; H4: Transformation to hydrogen type: Pickling solution preparation: prepare 1N hydrochloric acid solution, Flow rate: In ion exchange columns, it is controlled at 6 times the volume of resin processed per hour; Flow rate: Maintain the flow rate at 2L / min to ensure adequate contact and transformation; Transformation time: Keep stirring and maintain temperature for 3 hours, then let stand for 1.5 hours to complete the transformation; The resin was thoroughly washed with a large amount of deionized water until the pH value of the washing solution was close to neutral, thereby obtaining a resin catalyst.

[0034] The ultraviolet light parameters are: Light source type: Use medium pressure mercury lamp as UV light source; Wavelength range: The main wavelength is between 300nm; Irradiation distance: Keep the distance between the sample and the light source about 20cm; Irradiation time: usually 30 minutes, depending on the reaction progress.

[0035] Example 3 A method for preparing N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide, the operating steps of which are: S1: Weigh 40g 1,4-dihydroxyanthraquinone, 16g 1,4-dihydroxyanthraquinone leuco form, 50g p-phenylenediamine, 8g resin acid catalyst, 2g organic acid, 450g solvent, and heat to react; S2: After the reaction is completed, filter and distill to remove the solvent; S3: Continue to add dilute alkali solution, stir at 85°C for 50 minutes, filter, wash with water until neutral, and dry to obtain a condensation material; S4: Add 180 g of acetic acid and 90 g of acetic anhydride to the condensation material, heat the reaction, filter, wash to neutrality, and dry to obtain N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide.

[0036] The organic acid is formic acid.

[0037] The solvent is n-butanol.

[0038] The reaction temperature of S1 is 90°C and the reaction time is 14 hours.

[0039] The reaction temperature of S4 is 105°C and the reaction time is 140 minutes.

[0040] The preparation method of the resin acid catalyst is: H1: Preparation of Vinyl D006 Sodium Polystyrene Sulfonic Acid Resin by Acylation Add 120g of D006 sodium polystyrene sulfonic acid resin, 1150g of ethylene sulfonyl chloride and 12g of zinc chloride into reaction equipment 1, and react at 25°C for 18 hours; after the reaction is completed, filter and dry to obtain vinyl D006 sodium polystyrene sulfonic acid resin; H2: Mixed reactants To the sodium vinyl D006 polystyrene sulfonic acid resin obtained in H1, 8 g of 2,3-dimercaptosuccinic acid, 0.6 g of 3-vinylquinoline (CAS No.: 67752-31-2), 1200 g of toluene, and 0.03 g of a photoinitiator were added, and stirred at room temperature for 140 minutes; H3: Polymerization under UV irradiation The mixture was exposed to UV light for 40 min to initiate the thiol-olefin click chemistry reaction; H4: Transformation to hydrogen type: Pickling solution preparation: prepare 1N hydrochloric acid solution, Flow rate: In ion exchange columns, it is controlled at 8 times the volume of resin processed per hour; Flow rate: Maintain the flow rate at 2L / min to ensure adequate contact and transformation; Transformation time: Keep stirring and maintain temperature for 3 hours, then let stand for 1.5 hours to complete the transformation; The resin was thoroughly washed with a large amount of deionized water until the pH value of the washing solution was close to neutral, thereby obtaining a resin catalyst.

[0041] The ultraviolet light parameters are: Light source type: Use medium pressure mercury lamp as UV light source; Wavelength range: The main wavelength is between 350nm; Irradiation distance: Keep the distance between the sample and the light source about 20cm; Irradiation time: usually 40 minutes, depending on the reaction progress.

[0042] Example 4 A method for preparing N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide, the operating steps of which are: S1: Weigh 48g 1,4-dihydroxyanthraquinone, 18g 1,4-dihydroxyanthraquinone leuco form, 55g p-phenylenediamine, 10g resin acid catalyst, 3g organic acid, 500g solvent, and heat to react; S2: After the reaction is completed, filter and distill to remove the solvent; S3: Continue to add dilute alkali solution, stir at 90°C for 60 minutes, filter, wash with water until neutral, and dry to obtain a condensation material; S4: Add 200 g of acetic acid and 96 g of acetic anhydride to the condensation material, heat the reaction, filter, wash to neutrality, and dry to obtain N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide.

[0043] The organic acid is acetic acid.

[0044] The solvent is butanol.

[0045] The reaction temperature of S1 is 100° C. and the reaction time is 15 hours.

[0046] The reaction temperature of S4 is 110° C. and the reaction time is 150 minutes.

[0047] The preparation method of the resin acid catalyst is: H1: Preparation of Vinyl D006 Sodium Polystyrene Sulfonic Acid Resin by Acylation Add 130g of D006 sodium polystyrene sulfonic acid resin, 1200g of ethylene sulfonyl chloride and 14g of zinc chloride into the reaction kettle 1, and react at 30°C for 20 hours; after the reaction is completed, filter and dry to obtain vinyl D006 sodium polystyrene sulfonic acid resin; H2: Mixed reactants To the sodium vinyl D006 polystyrene sulfonic acid resin obtained in H1, 10 g of 2,3-dimercaptosuccinic acid, 0.7 g of 3-vinylquinoline (CAS No.: 67752-31-2), 1300 g of toluene, and 0.04 g of a photoinitiator were added, and the mixture was stirred at room temperature for 150 minutes; H3: Polymerization under UV irradiation The mixture was exposed to UV light for 50 min to initiate the thiol-olefin click chemistry reaction; H4: Transformation to hydrogen type: Pickling solution preparation: prepare 1N hydrochloric acid solution, Flow rate: In ion exchange columns, it is controlled at 10 times the volume of resin processed per hour; Flow rate: Maintain the flow rate at 3L / min to ensure adequate contact and transformation; Transformation time: Keep stirring and maintain temperature for 4 hours, then let stand for 2 hours to complete the transformation; The resin was thoroughly washed with a large amount of deionized water until the pH value of the washing solution was close to neutral, thereby obtaining a resin catalyst.

[0048] The ultraviolet light parameters are: Light source type: Use medium pressure mercury lamp as UV light source; Wavelength range: The main wavelength is between 400nm; Irradiation distance: Keep the distance between the sample and the light source about 20cm; Irradiation time: depends on the reaction progress, usually 50 minutes.

[0049] Comparative Example 1 No resin acid catalyst was added, and the rest was the same as in Example 1.

[0050] Comparative Example 2 The other steps were the same as in Example 1 except that 2,3-dimercaptosuccinic acid was not added.

[0051] Comparative Example 3 The other steps were the same as in Example 1 except that 3-vinylquinoline was not added.

[0052] Table 1 purity / % Yield / % Example 1 98.3 90.8 Example 2 98.7 91.2 Example 3 99.1 91.6 Example 4 99.3 92.1 Comparative Example 1 91.4 78.5 Comparative Example 2 92.6 85.7 Comparative Example 3 93.9 86.3 Through the data analysis of the above examples and comparative examples, the N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide prepared by the present invention has higher purity and yield.

[0053] The above description is only a preferred embodiment of the present invention and does not limit the present invention in any form. Although the present invention has been disclosed as a preferred embodiment as above, it is not used to limit the present invention. Any technical personnel in this field can make some changes or modify the technical contents disclosed above into equivalent embodiments without departing from the scope of the technical solution of the present invention. However, any brief modifications, equivalent changes and modifications made to the above embodiments based on the technical essence of the present invention without departing from the content of the technical solution of the present invention are still within the scope of the technical solution of the present invention.

Claims

1. A method for preparing N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide, the operating steps of which are: S1: Weigh 32-48 parts of 1,4-dihydroxyanthraquinone, 10-18 parts of leuco form of 1,4-dihydroxyanthraquinone, 40-55 parts of p-phenylenediamine, 5-10 parts of resin acid catalyst, 1-3 parts of organic acid, and 300-500 parts of solvent by weight, and heat to react; S2: After the reaction is completed, filter and distill to remove the solvent; S3: Continue to add dilute alkali solution, stir at 70-90°C for 30-60 minutes, filter, wash with water until neutral, and dry to obtain a condensation material; S4: adding 100-200 parts of acetic acid and 62-96 parts of acetic anhydride to the condensation material, heating the reaction, cooling and filtering, washing to neutrality, and drying to obtain N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide; The resin acid catalyst is prepared by reacting vinyl D006 sodium polystyrene sulfonic acid resin, 2,3-dimercaptosuccinic acid and 3-vinylquinoline.

2. The method for preparing N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide according to claim 1, characterized in that: The organic acid is one of oxalic acid, malonic acid, formic acid, propionic acid and acetic acid.

3. The method for preparing N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide according to claim 1, characterized in that: The solvent is one of DMF, methanol, n-butanol, isobutanol and butanol.

4. The method for preparing N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide according to claim 1, characterized in that: The reaction temperature of S1 is 70-100°C and the reaction time is 10-15 hours.

5. The method for preparing N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide according to claim 1, characterized in that: The reaction temperature of S4 is 100-110° C. and the reaction time is 100-150 minutes.

6. The method for preparing N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide according to claim 1, characterized in that: The preparation method of the resin acid catalyst is: H1: Preparation of Vinyl D006 Sodium Polystyrene Sulfonic Acid Resin by Acylation Add 100-130 parts of D006 sodium polystyrene sulfonic acid resin, 1000-1200 parts of ethylene sulfonyl chloride, and 7-14 parts of zinc chloride into the reaction device 1, and react at 20-30° C. for 10-20 hours; after the reaction is completed, filter and dry to obtain vinyl D006 sodium polystyrene sulfonic acid resin; H2: Mixed reactants Add 3-10 parts of 2,3-dimercaptosuccinic acid, 0.2-0.7 parts of 3-vinylquinoline, 1000-1300 parts of toluene, and 0.003-0.04 parts of photoinitiator to the sodium vinyl D006 polystyrene sulfonic acid resin obtained in H1, and stir at room temperature for 120-150 minutes; H3: Polymerization under UV irradiation Exposing the mixture to ultraviolet light for 20-50 minutes to initiate a thiol-olefin click chemistry reaction; H4: Transformation to hydrogen type: Pickling solution preparation: prepare 1N hydrochloric acid solution, Flow rate: In ion exchange columns, it should be controlled at 5-10 times the volume of resin processed per hour; Flow rate: Maintain the flow rate at 1-3L / min to ensure adequate contact and transformation; Transformation time: Keep stirring and maintain temperature for 2-4 hours, then let stand for 1-2 hours to complete the transformation; The resin was thoroughly washed with a large amount of deionized water until the pH value of the washing solution was close to neutral, thereby obtaining a resin catalyst.

7. The method for preparing N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide according to claim 6, characterized in that: The ultraviolet light parameters are: Light source type: Use medium pressure mercury lamp as UV light source; Wavelength range: The main wavelength is between 250-400nm; Irradiation distance: Keep the distance between the sample and the light source about 20cm; Irradiation time: usually 20-50 minutes, depending on the reaction progress.