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Process for isolation of monophenolic-bisaryl triazines

A technology of aryl and aroyl, applied in the field of separation of monohydric phenol-diaryl triazine compounds

Inactive Publication Date: 2004-11-17
CYTEC TECH CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the selectivity is not 100% and the subsequent reaction with resorcinol in a single reactor (pot) process forms small amounts of unwanted polyresorcinol impurities and tri-aryl-triazines

Method used

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  • Process for isolation of monophenolic-bisaryl triazines
  • Process for isolation of monophenolic-bisaryl triazines
  • Process for isolation of monophenolic-bisaryl triazines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0094] Example 1: Treatment with 5% aqueous sodium carbonate to isolate 2-(2,4-dihydroxyphenyl)- 4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine

[0095] a. Preparation of 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine (according to WO 00 / 29392)

[0096] A reaction flask equipped with a reflux condenser, nitrogen inlet and mechanical stirrer was charged with 50 g cyanuric chloride, 191 ml o-dichlorobenzene (ODCB) and 108.5 gm aluminum chloride. The mixture was placed in an ice bath, cooled to 5°C, and then 6.5 gm of concentrated hydrochloric acid was added over 20 minutes. The mixture was warmed to room temperature and stirred for 2 hours. It was cooled again to 5°C and then 51.8 gm of m-xylene was added slowly over 4 hours while allowing the temperature to rise to 21°C. The mixture was stirred at room temperature for another 16 hours. The reaction mixture was heated to approximately 69°C and 32.8 gm m-xylene was added over 30 minutes. The mixture wa...

Embodiment 2

[0100] Example 2: Isolation of 2-(2,4-dihydroxyphenyl)-4,6-bis by treatment with 3% aqueous sodium carbonate (2,4-Dimethylphenyl)-1,3,5-triazine

[0101] Add 112.5 ml of 3% aqueous sodium carbonate solution and 50 gm of the crude polyresorcinol-triazine impurity prepared in Example 1a to a reaction flask equipped with a reflux condenser, a Dean-Stark apparatus, a nitrogen inlet, and a mechanical stirrer. 2-(2,4-Dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine. The resulting mixture was heated to reflux and held at reflux for 2 hours and the residual ODCB was collected as an azeotrope in a Dean-Stark apparatus. Heating was stopped, the mixture was filtered at about 80°C, and the filter cake was washed with 112.5 ml of 3% aqueous sodium carbonate and 300 ml of 50°C water. A residue of 47 g thus obtained was analyzed by HPLC as 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)- 1,3,5-Triazine.

[0102] a. Separation of polyresorcinol-triazines

[0103] The ...

Embodiment 3

[0104] Example 3: Treatment with aqueous sodium hydroxide solution isolated 2-(2,4-dihydroxyphenyl)-4,6-bis (2,4-Dimethylphenyl)-1,3,5-triazine

[0105]Into a reaction flask equipped with a reflux condenser, a Dean-Stark apparatus, a nitrogen inlet, and a mechanical stirrer was added 50 gm of the crude 2-(2,4-dihydroxy phenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, followed by the addition of 175 ml of 0.25% aqueous sodium hydroxide solution. The reaction mixture was heated to reflux and the residual ODCB was collected as an azeotrope in a Dean-Stark apparatus. An additional 175 ml of 0.25% aqueous sodium hydroxide solution was added to maintain the pH at about 10, and reflux was continued for 1 hour. Heating was stopped, the mixture was filtered, and the filter cake was washed successively with 30 ml of 0.25% aqueous sodium hydroxide solution and 500 ml of water. Analysis of the product (47 gm) by HPLC revealed no detectable residues in 2-(2,4-dihydroxyphenyl)-4,6-...

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Abstract

This invention relates to a novel, efficient, economic and general-purpose process for isolating monophenolic-bisaryl triazine compounds from polyphenolic-triazines compounds and other impurities. More specifically, this invention relates to a process for isolating the monophenolic-bisaryl triazine compounds by contracting it with a base, an alcohol or a hydrocarbon solvent.

Description

field of invention [0001] The present invention relates to a new efficient and economical general method for separating monohydric phenol-diaryl triazine compounds from polyphenol-triazine compounds and other impurities. More specifically, the present invention relates to a process for isolating monohydric phenol-diaryltriazine compounds by contacting them with bases, alcohols or hydrocarbon solvents. Background of the invention [0002] Many materials, especially polymeric materials, degrade when exposed to sunlight and other sources of ultraviolet radiation. Polymeric materials such as plastics can discolor and / or become brittle with prolonged exposure to UV light. Therefore, many UV light absorbers, stabilizers and other materials capable of suppressing this degradation have been developed. Other areas of application for UV absorbers include cosmetics (eg sunscreens), fibers, spandex, inks, photographic materials and dyes. [0003] A known class of UV absorbers are com...

Claims

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Application Information

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IPC IPC(8): C07D251/24
CPCC07D251/24
Inventor R·B·古普塔H·辛格R·C·卡帕多那
Owner CYTEC TECH CORP
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