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Ketone oxime ester photoinitiator green synthetic method

A photoinitiator and green synthesis technology, applied in the preparation of sulfides, organic chemistry, etc., can solve the problems of increased use of acid chlorides and catalysts, increased costs, waste of raw materials, etc., to reduce post-processing operations, low production costs, The effect of reducing production costs

Inactive Publication Date: 2016-04-27
TIANJIN INGENOCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Existing generally use catalysts such as aluminum trichloride, zinc chloride to carry out Friedel-Crafts acylation reaction to synthesize the diphenyl sulfide acyl substituent of the first step, as patent CN1178902c, CN101565472B, this method has following disadvantages: ① trichloro Catalysts such as aluminum chloride and zinc chloride are easy to hydrolyze and release hydrogen chloride, causing pollution; ② catalysts such as aluminum trichloride and zinc chloride can complex with acid chlorides and product ketones, resulting in increased use of acid chlorides and catalysts, resulting in waste of raw materials, Increased cost; ③ catalysts such as aluminum trichloride and zinc chloride produce a large amount of acidic wastewater during post-treatment, and are difficult to recycle, causing a large amount of pollution

Method used

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  • Ketone oxime ester photoinitiator green synthetic method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] a. Preparation of diphenyl sulfide cyclopentyl acetone

[0033] Add 111.8g of diphenyl sulfide (0.6mol), 1mol of zirconium catalyst and 600ml of dichloromethane into a four-necked flask equipped with an electric stirrer and a thermometer, pass through nitrogen protection, and reduce the temperature of the reaction solution to -5~ 0°C, then dropwise added a mixed solution of 126.9g octanoyl chloride (0.78mol) and 150g of dichloromethane, after the dropwise addition was completed, the temperature was raised to 15°C and stirring was continued for 2 hours. After the reaction was completed, the reaction solution was poured into 2000ml of 1mol / L dilute sulfuric acid, and the lower organic phase was separated. The aqueous phase was extracted with 300 ml of dichloromethane. The organic phases were combined, washed once with 500ml of saturated sodium bicarbonate solution, and then washed three times with 500ml of water until neutral, added 200g of anhydrous magnesium sulfate fo...

Embodiment 2

[0039] a. Preparation of diphenyl sulfide cyclopentyl acetone

[0040] Add 111.8 g of diphenyl sulfide (0.6 mol), 2 mol of zirconium catalyst and 500 ml of chloroform into a four-necked flask equipped with an electric stirrer and a thermometer, pass through nitrogen protection, and lower the temperature of the reaction solution to 0-5°C. Then, a mixed solution of 146.4 g of octanoyl chloride (0.9 mol) and 200 g of chloroform was added dropwise, and after the dropwise addition, the temperature was raised to 15° C. and stirring was continued for 2 hours. After the reaction was completed, the reaction solution was poured into 2000ml of 2mol / L dilute hydrochloric acid, and the lower organic phase was separated. The aqueous phase was extracted with 300 ml of chloroform. Combine the organic phases, wash once with 500ml of saturated sodium bicarbonate solution, then wash three times with 500ml of water until neutral, add 200g of anhydrous magnesium sulfate to dry, and distill off ch...

Embodiment 3

[0046] a. Preparation of diphenyl sulfide cyclopentyl acetone

[0047] Add 111.8g of diphenyl sulfide (0.6mol), 3mol of zirconium catalyst and 700ml of dichloroethane into a four-necked flask equipped with an electric stirrer and a thermometer, pass through nitrogen protection, and reduce the temperature of the reaction solution to 0~ 5°C, and then dropwise added a mixed solution of 107.4g octanoyl chloride (0.66mol) and 200g of dichloroethane, and after the dropwise addition was completed, the temperature was raised to 15°C and stirring was continued for 2 hours. After the reaction was completed, the reaction solution was poured into 2000ml of 2mol / L dilute hydrochloric acid, and the lower organic phase was separated. The aqueous phase was extracted with 300 ml dichloroethane. Combine the organic phases, wash once with 500ml of saturated sodium bicarbonate solution, then wash three times with 500ml of water until neutral, add 200g of anhydrous magnesium sulfate to dry, and d...

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Abstract

The present invention discloses a ketone oxime ester photoinitiator green synthetic method. According to the method, diphenyl sulfide as a raw material is condensed with caprylyl chloride under the effect of a zirconium catalyst, and then a ketone oxime ester photoinitiator can be obtained by oximation and esterification. The method does not relate to high temperature and high pressure reaction, and is mild in reaction conditions, and good in security. No aluminum chloride or zinc waste water is produced due to use of the zirconium catalyst during the synthesis process, produced byproducts can be recycled, no environmentally harmful solvent is used, and the ketone oxime ester photoinitiator green synthetic method is environmentally friendly, and therefore suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of new materials, in particular to a preparation method of a ketoxime ester photoinitiator. Background technique [0002] Ketoxime ester photoinitiator Oxe-1 is mainly used in the photocuring process of unsaturated resin monomer materials, especially in the production process of optical filters of liquid crystal materials. [0003] Existing generally use catalysts such as aluminum trichloride, zinc chloride to carry out Friedel-Crafts acylation reaction to synthesize the diphenyl sulfide acyl substituent of the first step, as patent CN1178902c, CN101565472B, this method has following disadvantages: ① trichloro Catalysts such as aluminum chloride and zinc chloride are easy to hydrolyze and release hydrogen chloride, causing pollution; ② catalysts such as aluminum trichloride and zinc chloride can complex with acid chlorides and product ketones, resulting in increased use of acid chlorides and catalysts, resulting in wa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/20C07C323/47C07C323/22C08F2/48
CPCC07C319/20C08F2/48
Inventor 覃湘东刘彦春贾俊国
Owner TIANJIN INGENOCHEM TECH CO LTD
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