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Preparation method of quinacridone intermediate

A technology of quinacridone and intermediates, which is applied in the preparation of organic compounds, chemical instruments and methods, and cyanide reaction preparation, etc., which can solve the problems of large environmental pollution, high energy consumption, and large amounts of organic waste, and achieve reduction The effect of organic waste

Inactive Publication Date: 2016-02-24
WENZHOU JINYUAN CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the crude pigment particles prepared by this process route are very coarse, and the subsequent pigmentation requires ball milling or kneading, which consumes a lot of energy and pollutes the environment.
[0007] In CN1554709, it is mentioned that diethyl succinate undergoes a series of chemical reactions to generate 2,5-diphenylamino-3,6-dihydroterephthalic acid diethyl ester compound, and then oxidizes, hydrolyzes, and closes the ring to prepare quinacridine Ketone Pigment Red 122, the oxidizing agent used in the oxidation reaction is sodium m-nitrobenzene sulfonate. The disadvantage of this method is that a large amount of organic waste is generated due to the reduction of aromatic by-products during the synthesis of intermediates

Method used

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  • Preparation method of quinacridone intermediate
  • Preparation method of quinacridone intermediate
  • Preparation method of quinacridone intermediate

Examples

Experimental program
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Effect test

Embodiment 1

[0060]Add 500 parts of methanol, 69.4 parts of p-toluidine, 70 parts of dimethyl succinyl succinate, 1.3 parts of hydrochloric acid (31%) and 0.6 parts of concentrated sulfuric acid (98%) in sequence, into 1500 parts of the reaction kettle, and stir For 20 minutes, heat up to reflux, reflux for 4 hours, cool down to 55°C, control at 50-60°C, add 0.7 parts of anthraquinone-2,6-sodium disulfonate, add 90 parts of 30% hydrogen peroxide in 60 minutes, and complete the addition Stir for 5 minutes, add 160 parts of 50% sodium hydroxide in 30 minutes, stir for 20 minutes after adding, heat up to reflux, reflux for 4 hours, cool down to 65°C, add 190 parts of water, stir for 10 minutes, add 1060 parts of water, filter, Collect the filtrate. Measure the pH value of the filtrate, acidify and precipitate with 15% hydrochloric acid, take 30-60 minutes, adjust the pH value to 2.0, stir for 30 minutes, filter, wash the filter cake with tap water, dry and pulverize to obtain the finished int...

Embodiment 2

[0067] Add 680 parts of ethanol, 95 parts of aniline, 87.3 parts of dimethyl succinyl succinate, 4 parts of hydrochloric acid (31%) and 4 parts of concentrated sulfuric acid into the autoclave successively, stir for 20 minutes, seal the autoclave, and heat up to 95°C, keep warm for 3 hours, cool down to 5-55°C, add 0.9 parts of anthraquinone-2,6-sodium disulfonate, add 150 parts of 30% hydrogen peroxide in 90 minutes, stir for 5 minutes, use at 50-60°C Add 210 parts of 50% potassium hydroxide in 30 minutes, stir for 20 minutes after adding, seal the autoclave, heat up to 95°C and keep it for 4 hours, cool down to 60°C, add 3500 parts of water, stir for 15 minutes, keep the temperature at about 35°C, filter , wash the filter residue with 350 parts of water, merge into the filtrate, collect the filtrate, adjust the pH value to 1.5 with 30% sulfuric acid, stir for 30 minutes, retest the pH value should be 1.5, filter, wash with tap water, dry and pulverize to obtain the intermedia...

Embodiment 3

[0073] Add 680 parts of ethanol, 20 parts of aniline, 85 parts of p-toluidine, 87.5 parts of dimethyl succinylate, 2 parts of 31% hydrochloric acid and 0.8 parts of concentrated sulfuric acid into the autoclave in sequence, stir for 20 minutes, and seal the pressure Kettle, heat up to 100°C, keep warm for 4 hours, cool down to 50-60°C, add 1.8 parts of anthraquinone-2,6-sodium disulfonate, add 150 parts of 30% hydrogen peroxide in 60 minutes, stir for 5 minutes, at 50- Add 210 parts of 50% potassium hydroxide in 30 minutes at 60°C, stir for 20 minutes, heat up to 100°C, keep warm for 3 hours, cool down to 60°C, add 3500 parts of water, the temperature is about 35°C, filter, and wash the filter residue with 350 parts of water , merged into the filtrate, collected the filtrate, adjusted the pH value to 1.5 with 31% hydrochloric acid, stirred for 30 minutes, retested the pH, filtered, washed with tap water, dried, and pulverized to obtain the intermediate product. 127 parts were ...

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Abstract

The invention belongs to the industry of pigment and relates to an environment-friendly quinacridone intermediate, namely 2, 5-diphenylamino terephthalic acid, and a preparation method of a derivative thereof. The preparation method of the quinacridone intermediate is as indicated in the formula (1), wherein X and Y are selected from H, F, Cl, CH<3> or OCH<3> in a mode that X and Y are independent of each other. The preparation method of the quinacridone intermediate comprises the steps that dimethyl succinylo succinate and aniline or an aniline derivative or a mixture of aniline and the aniline derivative are condensed in an alcohol medium under catalysis of acid, 2, 5-diphenylamino-3, 6-dihydro dimethyl terephthalate and a derivative thereof are obtained, then hydrogen peroxide serves as oxidant, oxidation and hydrolysis are conducted on 2, 5-diphenylamino-3, 6-dihydro dimethyl terephthalate and the derivative thereof in the water-containing alkaline alcohol medium, subsequently, acidification is conducted, and the quinacridone pigment key intermediate, namely 2, 5-diphenylamino terephthalic acid, and the derivative thereof are obtained. According to the preparation method of the quinacridone intermediate, no reducing aromatic by-product is generated, organic waste is greatly reduced, and environmental value and economic value are achieved.

Description

technical field [0001] The invention belongs to the pigment industry, and relates to a preparation method of an environment-friendly quinacridone intermediate: 2,5-dianilinoterephthalic acid and derivatives thereof. Background technique [0002] Quinacridone pigments have the general formula: [0003] [0004] Wherein, X and Y are independently selected from H, F, Cl, CH3, OCH3. [0005] Quinacridone pigments have good molecular symmetry, good molecular planarity and can form intermolecular hydrogen bonds, so quinacridone pigments have excellent heat resistance, and can withstand 300 °C in polyolefin plastics, solvent resistance, and light resistance. It is a very important class of high-performance organic pigments, which are widely used in many fields such as coatings, plastics, inks, melt spinning and cosmetics, and can be used in electronic photography and color copying. Used as a functional pigment. [0006] CN1207402, CN1077124, CN100349988, CN100358949, CN102585...

Claims

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Application Information

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IPC IPC(8): C07C229/62C07C227/18
CPCC07C227/08C07C227/18C07C229/48C07C229/62
Inventor 黄日新
Owner WENZHOU JINYUAN CHEM CO LTD
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