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Method for preparing 2-(2,4-dihydroxyphenyl)-4,6-diphenyl-1,3,5-triazine

A technology of dihydroxyphenyl and diphenyl, which is applied in the field of preparation of 2--4,6-diphenyl-1,3,5-triazine, can solve the problem of lack of economic attractiveness, difficulty in recycling, Long synthetic route and other problems, to avoid the pressure of three wastes treatment, overcome the non-reusable, mild reaction conditions

Inactive Publication Date: 2019-01-11
DALIAN RES & DESIGN INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method greatly simplifies the synthesis process, it still uses a large amount of anhydrous aluminum trichloride as a catalyst, which cannot avoid the environmental pressure brought by a large amount of acidic wastewater.
CN106083751A takes benzonitrile as the starting material, synthesizes 2-(2,4-dihydroxyphenyl)-4,6-diphenyl-1,3,5-triazine through three steps, the process is loaded down with trivial details, and after During the treatment process, the reaction solvent dimethyl sulfoxide is difficult to recycle after mixing with water, and the product yield is low, which is not suitable for industrial production
There is also the condensation synthesis ring method adopted by the patent US5705643, the raw materials used are highly toxic, the synthetic route is long, it is not suitable for industrial scale production, and it lacks economic attractiveness

Method used

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  • Method for preparing 2-(2,4-dihydroxyphenyl)-4,6-diphenyl-1,3,5-triazine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] In the 250ml reaction flask, add 40g 1-butyl-3-methylimidazolium chloroaluminate ionic liquid ( [Bmim]Cl-2AlCl 3 ) and 18.45g (0.1mol) cyanuric chloride, add 15.6g (0.2mol) benzene dropwise under stirring condition at 15~20°C, finish adding in 4h, and keep warm at 15~20°C for 24h after dropping, with 210nm wavelength Under the condition of liquid chromatographic analysis, the content of cyanuric chloride is 1.5%.

[0024] The temperature of the above reaction solution was raised to 80°C, and 11 g (0.1 mol) of resorcinol was added in batches, and the addition was completed within 2 hours, during which a yellow solid was precipitated. After the addition, the reaction was kept for 4 hours.

[0025] Add 100ml of o-dichlorobenzene into the reaction bottle, stir well at 80°C, keep warm and let it stand for stratification. The chloroaluminate ionic liquid in the lower layer is recovered for the next reaction and reused. After the upper layer is cooled, a solid is precipitated...

Embodiment 2

[0027] In the 250ml reaction bottle, add 80g by the 1-ethyl-3-methylimidazolium chloroaluminate ionic liquid ( [Emim]Cl-1.8AlCl 3 ) and 18.45g (0.1mol) cyanuric chloride, add 16.38g (0.21mol) benzene dropwise under stirring condition at 20~25°C, add it in 4h, and keep it at 20~25°C for 12h after the dropwise addition, 210nm wavelength Under the condition of liquid chromatography analysis, the content of cyanuric chloride is 1.8%.

[0028] The temperature of the above reaction solution was raised to 75°C, and 9.9 g (0.09 mol) of resorcinol was added in batches, and the addition was completed within 2 hours, during which a yellow solid was precipitated. After the addition, the reaction was kept for 6 hours.

[0029] Add 100ml of chlorobenzene into the reaction flask, stir well at 75°C, keep warm and let stand for stratification. The chloroaluminate ionic liquid in the lower layer is recovered for the next reaction and reused. After the upper layer is cooled, the solid is precip...

Embodiment 3

[0031] In the 250ml reaction bottle, add 100g by aluminum trichloride and 1-butyl-4-picoline chloride 1-butyl-4-picoline molar ratio 2.2:1 mix the 1-butyl-4-picoline chloroaluminate ionic liquid that obtains ( [Bmp]Cl-2.2AlCl 3 ) and 18.45g (0.1mol) cyanuric chloride, add 14.04g (0.18mol) benzene dropwise under stirring condition at 25~30°C, finish adding in 2h, and keep warm for 8h at 25~30°C after dropping, at 210nm wavelength Under the condition of liquid chromatographic analysis, the content of cyanuric chloride was 1.6%.

[0032] The temperature of the above reaction solution was raised to 85°C, and 12.1 g (0.11 mol) of resorcinol was added in batches, and the addition was completed within 4 hours, during which a yellow solid was precipitated, and after the addition was completed, the reaction was kept for 8 hours.

[0033] Add 80ml of o-dichlorobenzene into the reaction bottle, stir well at 85°C, keep it warm and let it stand for stratification. The chloroaluminate ioni...

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Abstract

The invention discloses a method for preparing 2-(2,4-dihydroxyphenyl)-4,6-diphenyl-1,3,5-triazine. The method comprises the following steps: taking cyanuric chloride and benzene as initial raw materials, taking aluminum chlorate ionic liquid as a reaction solvent and a catalyst, and producing an intermediate I; reacting the intermediate I and resorcinol without separation, thereby obtaining the 2-(2,4-dihydroxyphenyl)-4,6-diphenyl-1,3,5-triazine. The 2-(2,4-dihydroxyphenyl)-4,6-diphenyl-1,3,5-triazine is extracted from the ionic liquid catalyst by adopting an extraction agent, so that separation between the product and the catalyst is realized. The aluminum chlorate ionic liquid can be repeatedly used, the pressure of the traditional aluminum chloride anhydrous catalyst on treatment of three wastes is avoided, and the green and environmental-friendly requirements are met.

Description

technical field [0001] The invention belongs to the field of fine chemicals, and in particular relates to a preparation method of 2-(2,4-dihydroxyphenyl)-4,6-diphenyl-1,3,5-triazine. Background technique [0002] Triazine UV absorber is a kind of UV absorber with high absorption performance, broad spectrum, strong heat resistance and good dispersibility. It is widely used in polymer materials such as plastics, polyurethanes, and coatings. It can effectively prevent products from being damaged by ultraviolet rays. The aging caused by it enhances the color stability of the product and prolongs the service life of the material. 2-(2,4-dihydroxyphenyl)-4,6-diphenyl-1,3,5-triazine ( ) is an important intermediate for the preparation of triazine UV absorbers UV-1577 and UV-1579. [0003] [0004] In "Synthesis and characterization of a s-triazine UV absorber UV-1577" (Zhejiang Chemical Industry, No. 3, 2009), Song Guangwei et al. used cyanuric chloride, bromobenzene, and m...

Claims

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Application Information

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IPC IPC(8): C07D251/24
CPCC07D251/24
Inventor 孟纪文刘威韩建国
Owner DALIAN RES & DESIGN INST OF CHEM IND
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