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

A technology of alkyl imidazole tetrafluoroborate and alkyl pyridine tetrafluoroborate, applied in the field of preparing 2--4, can solve problems such as yield restriction, inability to recover and apply aluminum trichloride, and reduce pollution , the recycling process is simple and easy to implement, and the effect of saving catalyst costs

Active Publication Date: 2019-11-12
RIANLON +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] In view of this, the present invention aims at the problem that the catalyst aluminum trichloride cannot be recycled or recycled and applied in the synthetic process of the ultraviolet absorber intermediate, and the problem that a large amount of acid water is produced during the processing of aluminum trichloride restricts the yield, and provides An economical and environment-friendly method for preparing 2-(2,4-dihydroxyphenyl)-4,6-bisaryl-1,3,5-triazine with simple operation and no need for aluminum trichloride

Method used

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

Examples

Experimental program
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Effect test

Embodiment 1

[0050]Example 1: Add 550ml of 1-butyl-3-methylimidazolium tetrafluoroborate, 55ml of o-dichlorobenzene, 55.4g (0.30mol) of cyanuric chloride into the reactor, stir and cool down to 5°C, 46.8g (0.60mol) of benzene was added dropwise, and the dropwise addition time was 2h. While adding benzene dropwise, 3.2g of initiator HCl gas was introduced (completed within 1h), and the temperature was kept at 5-10°C. ~15°C heat preservation reaction for 12 hours, HPLC detection of 2-chloro-4,6-diphenyl-1,3,5-triazine content in the reaction solution was 95.2%, the HPLC spectrum is as follows figure 1 As shown, the peak elution time is consistent with the peak elution time of the standard product; add 34.2g (0.31mol) of resorcinol, stir and heat up to 70-80°C, keep the temperature for 12h, cool down to 20°C to filter out the crude product, and recover the filtrate Apply mechanically, the crude product is refined with methanol to obtain 2-(2,4-dihydroxyphenyl)-4,6-bisphenyl-1,3,5-triazine con...

Embodiment 2

[0051] Example 2: Add 200ml of 1-hexyl-3-methylimidazolium tetrafluoroborate and 100ml of 1-butyl-3-methylimidazolium tetrafluoroborate to the reactor, 55.4g (0.30mol) With cyanuric chloride, stir and cool down to 5°C, add dropwise 46.8g (0.60mol) of benzene, and the dropwise addition time is 3h, while adding dropwise benzene, feed 2.2g of initiator HCl gas (pass through within 1h), keep the temperature at 5~10°C, after the addition of benzene, keep it warm at 10~15°C for 6 hours, HPLC detects that the content of 2-chloro-4,6-diphenyl-1,3,5-triazine in the reaction solution is 94.6%, add m-benzene Diphenol 34.2g (0.31mol), stir and heat up to 90-100°C, heat preservation reaction for 8h, cool down to 20°C to filter out the crude product, recover the filtrate for mechanical use, and refine the crude product with methanol to obtain 2-(2,4-dihydroxyphenyl) - 4,6-bisphenyl-1,3,5-triazine content of 99.2% product, yield 90.5%.

Embodiment 3

[0052] Example 3: Add 200ml of 1-pentyl-3-methylimidazolium tetrafluoroborate and 220ml of 1-butyl-3-methylimidazolium tetrafluoroborate to the reactor, 110ml o-dichlorobenzene , 55.4g (0.30mol) cyanuric chloride, stirring to cool down to 5 ℃, dropwise adding 46.8g (0.60mol) of benzene, the dropping time is 3h, while adding benzene, feed 2.7g of initiator HCl gas (1.5h After passing through), keep the temperature at 5-10°C, and keep the temperature at 10-15°C for 9h after the addition of benzene, and detect 2-chloro-4,6-diphenyl-1,3,5-triazine in the reaction solution by HPLC Content 95.0%, add resorcinol 34.2g (0.31mol), stir and heat up to 80-90°C, heat preservation reaction for 10h, cool down to 20°C to filter out the crude product, recover the filtrate for mechanical use, and refine the crude product with methanol to obtain 2-(2, 4-dihydroxyphenyl)-4,6-bisphenyl-1,3,5-triazine with a content of 99.4% and a yield of 91.9%.

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Abstract

The invention provides a method for preparing 2-(2,4-dihydroxyphenyl)-4,6-bisaryl-1,3,5-triazine. In the existence of a tetrafluoroborate ionic liquid and HCl gas, cyanuric chloride and an aromatic hydrocarbon react to form a compound of a formula I; the compound of the formula I is reacted with resorcinol to form a compound of a formula II. The method avoids the use of aluminum trichloride, and achieves clean production and green chemical industry. A catalyst adopted in the method can be recycled and used for multiple times, thus effectively saving the cost.

Description

technical field [0001] The invention belongs to the technical field of synthesis of triazine ultraviolet absorber intermediates, in particular to a method for preparing 2-(2,4-dihydroxyphenyl)-4,6-bisaryl-1,3,5-triazine Methods. Background technique [0002] As we all know, triazine ultraviolet absorber intermediates are an important class of fine chemical products, which have the advantages of light color, high temperature resistance, wide range of ultraviolet absorption, and good compatibility with polymers and other additives. Dominating the market. The chemical formula of common triazine UV absorber intermediate is shown in formula (II), wherein R is H or CH 3 . When R is H, the intermediate 2-(2,4-dihydroxyphenyl)-4,6-bisphenyl-1,3,5-triazine is one of the main raw materials for the synthesis of UV absorber UV-1577 One; when R is CH 3 , this intermediate 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine is a synthetic triazine UV-absorbing One of ...

Claims

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Application Information

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IPC IPC(8): C07D251/24
CPCC07D251/24Y02P20/584
Inventor 云会霞孙春光范小鹏张会京徐丁孙东辉熊昌武毕作鹏李海平
Owner RIANLON
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