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Preparation method of 2,9-dimethyl quinacridone purplish red pigment

A technology of dimethylquinacridone and dihydroquinacridone, which is applied in the field of preparation of 2,9-dimethylquinacridone purple pigment, can solve the problem of difficult removal and m-nitrobenzenesulfonate Toxicity and irritation, etc., to achieve the effect of reducing the cost of raw materials, reducing the cost of three wastes treatment, and reducing the amount of waste water produced

Inactive Publication Date: 2020-04-17
HEBEI CAIKE CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Oxidation in the reaction process usually uses oxidants such as dichromate, sodium chlorate, m-nitrobenzene sulfonate, and such oxidants will have a great impact on environmental protection and sewage treatment after use. For example, dichromate contains Heavy metal chromium is difficult to remove in the environment, m-nitrobenzene sulfonate is toxic and irritating, etc.

Method used

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  • Preparation method of 2,9-dimethyl quinacridone purplish red pigment
  • Preparation method of 2,9-dimethyl quinacridone purplish red pigment
  • Preparation method of 2,9-dimethyl quinacridone purplish red pigment

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Ring-closing process: succinate diester self-condenses in the presence of sodium methoxide to obtain the first intermediate product dimethyl succinylsuccinate, and then adds aniline or substituted aniline to the reaction system for condensation reaction to obtain the second The intermediate product 2,5-dianiline-3,6-dihydroterephthalic acid dimethyl ester, which undergoes a ring-closure reaction under the action of polyphosphoric acid PPA, obtains the third intermediate product 2,9-dimethyl- 6,13-Dihydroquinacridone.

[0025] Oxidation process: Add 2,9-dimethyl-6,13-dihydroquinacridone obtained through condensation and ring-closing reaction into the reaction vessel, then add onionone-2-sodium sulfonate to it, and use KOH solution Adjust the pH to 10-11, heat up to 90°C, slowly add hydrogen peroxide solution into the reaction vessel, and control the hydrogen peroxide, allthone-2-sodium sulfonate and 2,9-dimethyl-6,13-dihydroquinacridine The molar ratio of pyridone added...

Embodiment 2

[0028] Oxidation process: Add 2,9-dimethyl-6,13-dihydroquinacridone obtained through condensation and ring-closing reaction into the reaction vessel, then add onionone-2-sodium sulfonate to it, and use KOH solution Adjust the pH to 7-8, heat up to 90°C, slowly add hydrogen peroxide solution into the reaction vessel, control The molar ratio of pyridone added is 1.3:0.07:1, continue to heat up to 130-140°C, keep the temperature, react for 4h, and the reaction ends; cool down the reaction solution to 80°C, pour it into a beaker, add the same volume as the reaction solution cold water, stirred and cooled to room temperature, filtered, the filter cake was washed with methanol, beating for 1 hour, filtered and top washed to obtain the crude PR122.

[0029] The ring-closing process and purification process are the same as in Example 1. The yield of the obtained product pigment purple PR122 was 85.71%.

Embodiment 3

[0031] Oxidation process: Add 2,9-dimethyl-6,13-dihydroquinacridone obtained through condensation and ring-closing reaction into the reaction vessel, then add onionone-2-sodium sulfonate to it, and use KOH solution Adjust the pH to 9-10, heat up to 90°C, slowly add hydrogen peroxide solution into the reaction vessel, and control the hydrogen peroxide, sodium allium-2-sulfonate and 2,9-dimethyl-6,13-dihydroquinacridine The molar ratio of pyridone added is 1.6:0.06:1, continue to heat up to 120-130°C, keep the temperature, react for 4h, and the reaction ends; cool down the reaction solution to 80°C, pour it into a beaker, add the same volume as the reaction solution cold water, stirred and cooled to room temperature, filtered, the filter cake was washed with methanol, beating for 1 hour, filtered and top washed to obtain the crude PR122.

[0032] The ring-closing process and purification process are the same as in Example 1. The yield of the obtained product pigment purple PR12...

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Abstract

The invention discloses a preparation method of a 2,9-dimethyl quinacridone purplish red pigment. The 2,9-dimethyl quinacridone purplish red pigment is prepared by adopting a ring-closure reaction atfirst and an oxidation process next. The method comprises the following steps: adding 2,9-dimethyl-6,13-dihydroquinacridone obtained after a condensation reaction and the ring-closure reaction into areaction container; then adding a catalyst into the reaction container, adjusting a pH value to 7-11 by using a dilute alkali solution, and carrying out heating to 90 DEG C; slowly adding a hydrogen peroxide solution into the reaction container, controlling the adding molar ratio of hydrogen peroxide to the catalyst to 2, 9-dimethyl-6,13-dihydroquinacridone, continuing to heat to 105-140 DEG C, keeping the temperature, conducting a reaction for 3-4.5 hours and terminating the reaction; cooling a reaction solution to 80 DEG C, pouring the reaction solution into a beaker, adding cold water withthe same volume as the reaction solution, carrying out stirring, conducting cooling to room temperature, performing filtering, washing a filter cake with methanol, carrying out pulping for 1 hour, then conducing filtering, and carrying out top washing to obtain a crude PR122 product; and purifying the crude PR122 product. According to the method, hydrogen peroxide is adopted to replace a traditional oxidizing agent, and an oxidation process is optimized, so the purpose of improving product yield is achieved.

Description

technical field [0001] The invention relates to a preparation method of 2,9-dimethylquinacridone purple pigment, which belongs to the technical field of chemical preparation. Background technique [0002] Quinacridone pigments entered the market in 1958. Compared with the red and purple pigments used before, quinacridone has outstanding characteristics such as weather resistance, heat resistance, and solvent resistance. Positioned in the high-end products of organic pigments. [0003] The production process of 2,9-dimethylquinacridone pigment (pigment purple PR122) is representative in the production process of quinacridone pigments. The industry generally adopts the succinic acid diester method. The method has two processes of first oxidation reaction followed by ring-closing reaction and first ring-closure reaction followed by oxidation reaction. Oxidation process after ring closure, that is, the succinate diester controls the reaction temperature in the presence of sod...

Claims

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Application Information

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IPC IPC(8): C09B48/00C07D471/04
CPCC07D471/04C09B48/00
Inventor 任全胜张吉晔陶世刚王淑梅李祥金刘子洋赵国杰
Owner HEBEI CAIKE CHEM CO LTD
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