Method for recycling catalyst in aryl-s-triazine ultraviolet absorber prepared by Friedel-Crafts method

A s-triazine and ultraviolet light technology, applied in organic chemistry and other directions, can solve the problems of unrecyclable aluminum trichloride, high cost, environmental pollution, etc., to eliminate aluminum trichloride-containing wastewater and improve clean production. Effect

Active Publication Date: 2019-10-22
JIANGSU KAITENG PHARMA RAW MATERIALS CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The present invention aims at the problems that aluminum trichloride cannot be recycled and reused as a catalyst in the synthesis process of UV1164 and UV1577 and other aryl-s-triazine ultraviolet light absorbers, and the problem is that the cost is high and the environment is polluted. Method for catalyst aluminum trichloride in s-triazine class ultraviolet absorber intermediate

Method used

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  • Method for recycling catalyst in aryl-s-triazine ultraviolet absorber prepared by Friedel-Crafts method
  • Method for recycling catalyst in aryl-s-triazine ultraviolet absorber prepared by Friedel-Crafts method
  • Method for recycling catalyst in aryl-s-triazine ultraviolet absorber prepared by Friedel-Crafts method

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Experimental program
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Effect test

Embodiment 1

[0029] Add 3 liters of chlorobenzene, 184 grams of cyanuric chloride, 156 grams of benzene (2 times the amount) and 400 grams of aluminum chloride (3 times the amount) in 5 liters of there-necked flasks equipped with mechanical stirring; Add 20 milliliters of concentrated hydrochloric acid (0.2 times), stir and react for 1 hour, rise to room temperature and then heat to 90°C, add 1.2 kilograms of 1-methyl-3-ethylimidazole tetrachloroaluminate ionic liquid (imidazole / aluminum chloride =1:2), stirred for half an hour. The upper layer is the chlorobenzene solution, and the lower layer is the ionic liquid layer. After liquid separation, the chlorobenzene layer recovers part of the solvent, filters the precipitated solid, washes with water, and recrystallizes to obtain monochlorodiphenyl-1,3,5-tri 215 grams (81%) of oxazine; 1 gram of aluminum trichloride seed was added to the ionic liquid layer, cooled to room temperature, stirred slowly overnight, and 220 grams of powdered alumin...

Embodiment 2

[0031] Add 3 liters of chlorobenzene, 184 grams of cyanuric chloride, 156 grams of benzene (2 times the amount) and 400 grams of aluminum chloride (3 times the amount) in 5 liters of there-necked flasks equipped with mechanical stirring; Add 20 ml of concentrated hydrochloric acid (0.2 times), stir the reaction for 1 hour, rise to room temperature and add 121 g of resorcinol (1.1 times), then heat to 90° C. for 2 hours. After the reaction, add 1.2 kg of 1-methyl-3-ethylimidazole tetrachloroaluminate ionic liquid (imidazole / aluminum chloride = 1:2), stir for half an hour, then filter while hot, and filter the cake with 0.2 liter of chlorine Wash with benzene, and recrystallize the solid to obtain 228 grams of diphenyl-6-(1-resorcinyl)-1,3,5-triazine product (67% yield); add 1 gram of aluminum trichloride seed to the filtrate , cooled to room temperature, stirred slowly overnight, and filtered out 295 grams of powdery aluminum trichloride;

Embodiment 3

[0033] Add 3 liters of chlorobenzene, 184 grams of cyanuric chloride, 212 grams of m-xylene (2 times the amount) and 400 grams of aluminum chloride (3 times the amount) in a 5 liters there-necked flask equipped with mechanical stirring; ice water cooling Next, add 20 milliliters of concentrated hydrochloric acid (0.2 times), stir and react for 1 hour, rise to room temperature and heat to 90 ° C, then add 1.2 kilograms of 1-methyl-3-ethylimidazole tetrachloroaluminate ionic liquid (imidazole / aluminum chloride=1:2), stirred for half an hour. The upper layer is the chlorobenzene solution, and the lower layer is the ionic liquid layer. After liquid separation, the chlorobenzene layer recovers part of the solvent, and the solid is filtered to recrystallize to obtain the product monochloro-2,4-(1-m-xylyl)- 308 grams (95%) of 1,3,5-triazine; 1 gram of aluminum trichloride seed was added to the ionic liquid layer, stirred slowly at room temperature overnight, and 226 grams of precipi...

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Abstract

The invention discloses a method of recycling a catalyst used in Friedel-Crafts process for producing an aryl-s-triazine ultraviolet absorber. The method includes the following steps: 1) with chlorobenzene as a solvent, performing a Friedel-Crafts reaction to cyanuric chloride and aromatic hydrocarbon under a catalyst, AlCl3, to prepare a reaction solution which contains an intermediate of the aryl-s-triazine ultraviolet absorber; 2) adding a tetrachloroaluminate ionic liquid, as an extract agent, to the reaction solution so as to separate the intermediate of the aryl-s-triazine ultraviolet absorber from the AlCl3 or tetrachloroaluminate ions, and recycling the extracted and separated AlCl3 or tetrachloroaluminate ions as the catalyst or the extract agent for producing the aryl-s-triazineultraviolet absorber via the Friedel-Crafts process. In the method, the tetrachloroaluminate ionic liquid is used as the extract agent to separate the intermediate from the catalyst phase AlCl3, so that the catalyst, AlCl3, used in the Friedel-Crafts process can be recycled. The method eliminates waste water containing the AlCl3 without reduction on product yield, thus significantly improving clean production performance.

Description

technical field [0001] The invention relates to a method for preparing an intermediate of an aryl-s-triazine-type ultraviolet light absorber by the Friedel-Crafts method, in particular to a method for recycling the catalyst aluminum trichloride in the preparation of an aryl-s-triazine-type ultraviolet light absorber intermediate by the Friedel-Crafts method, belonging to the aromatic Synthesis of s-triazine-based UV absorbers. Background technique [0002] Aryl-s-triazine UV absorbers are an important class of fine chemical products. As additives, they are widely used in organic polymer materials such as plastics, coatings, and synthetic fibers. of aging. Among the numerous aryl-s-triazine UV absorbers, UV-1164 and UV-1577 (see the structural formula) figure 1 ) represented by 2,4-diaryl-6-(1-diphenolyl)-s-triazine-derived UV absorbers not only have low volatility, high absorption efficiency, strong absorption capacity, good high temperature resistance, and excellent color...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D251/22C07D251/24
Inventor 李斌刘文煜张月宝陈新宜孙国平
Owner JIANGSU KAITENG PHARMA RAW MATERIALS CO LTD
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