Method of producing 10-(4-xenyl)-2-isopropyl thioxanthone sulfur onium phosphorofluoric acid salt

A technology of isopropylthioxanthone and biphenyl is applied in the field of preparation of sulfonium salt compounds, and can solve the problems of poor product quality and high cost of production raw materials

Active Publication Date: 2008-04-02
INSIGHT HIGH TECH (BEIJING) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method of the present invention overcomes the shortcomings of high production raw material cost and poor product quality in the prior art method

Method used

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  • Method of producing 10-(4-xenyl)-2-isopropyl thioxanthone sulfur onium phosphorofluoric acid salt
  • Method of producing 10-(4-xenyl)-2-isopropyl thioxanthone sulfur onium phosphorofluoric acid salt
  • Method of producing 10-(4-xenyl)-2-isopropyl thioxanthone sulfur onium phosphorofluoric acid salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] In a 1000 ml four-necked flask, add 60.0 grams (0.24 moles) of 2-ITX (2-isopropylthioxanthone), 450 milliliters of acetonitrile and 100 milliliters of water, 18.0 grams of cerium ammonium nitrate (0.0328 moles), 10.0 grams 48% hydrobromic acid solution, after stirring evenly, keep the temperature at 25-30°C, add 200 grams (0.24 moles) of 10% sodium hypochlorite solution dropwise from the dropping funnel, stir for 24 hours and take a sample analysis, the content of raw material 2-ITX was 1.1%. Add 400 ml of water to the reaction solution, stir for 1 hour, then filter with suction, wash the filter cake with 100 ml of water, and dry to obtain 56.1 g of light yellow oxidation product. The purity by HPLC analysis was 97.4%, and the yield was 88.4%.

Embodiment 2

[0026] 20.5 grams (0.076 moles) of 2-ITX oxidation product (gained in Example 1) and 18.0 grams (0.117 moles) of biphenyl, 70 milliliters of acetic acid, 70 milliliters of acetic anhydride, 18 milliliters of dichloromethane, stirred in 250 milliliters four-necked flask Dissolve, then place in a low-temperature bath to cool down to below 15°C, add 26 ml of concentrated sulfuric acid dropwise, and keep the temperature of the reaction solution not higher than 15°C. After the dropwise addition, the mixture was stirred at 15°C for 2 hours. The reaction solution was transferred to a 2500 ml reaction bottle, 1000 ml of water and 1000 ml of dichloromethane were added, and after stirring for 30 minutes, the layers were separated in a separatory funnel, and the lower layer of dichloromethane solution was separated. Dichloromethane was evaporated to dryness on a rotary evaporator to obtain the bisulfate intermediate.

[0027] This intermediate was dissolved in 150 ml of methanol, and 25...

Embodiment 3

[0032]20.5 grams (0.076 moles) of 2-ITX oxidation product (gained in Example 1) and 18.0 grams (0.117 moles) of biphenyl, 70 milliliters of acetic acid, 70 milliliters of acetic anhydride, 18 milliliters of dichloromethane, stirred in 250 milliliters four-necked flask Dissolve, then place in a low-temperature bath to cool down to below 15°C, add 26 ml of concentrated sulfuric acid dropwise, and keep the temperature of the reaction solution not higher than 15°C. After the dropwise addition, the mixture was stirred at 15°C for 2 hours. Add 1000 milliliters of water and 1000 milliliters of dichloromethane, stir, and then transfer the reaction solution to a 2500 milliliter reaction flask. After 30 minutes, put in a separatory funnel to separate layers and separate the lower layer of dichloromethane solution. Dichloromethane was evaporated to dryness on a rotary evaporator to obtain the bisulfate intermediate.

[0033] This intermediate was dissolved in 150 ml of ethanol, and 250 ...

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Abstract

The present invention relates to a preparation method of novel cationic photoinitiator10-(4-biphenyl)-2-isopropyl-thiadiazole ketone sulfur hexafluorophosphate. The 2-isopropyl thioxanthone is used as raw material; the mixed oxidant of cerium ammonium nitrate and sodium hypochlorite is used; the hydrohalogenic acid is added for catalysis. After the oxidation reaction, the intermediate sulfoxide can be made; the sulfoxide and biphenyl react to get the intermediate of sulfonium salt through salt reaction. Finally, the mixed solvent of alcohol categories and water is used; and the aqueous solution potassium hexafluorophosphate is dropped into the solution of the intermediate sulfoxide to get the product. The method of the present invention can reduce the dosage of expensive oxidant, and quicken the speed of oxidation reaction. Besides, the ion exchange reaction is complete and the solvent is easy to be recycled and reused; the purity of the target product is high; the optical solidification effects are good; the whole process is easy for realization of industrial production.

Description

technical field [0001] The invention relates to a preparation method of a novel sulfonium salt compound without benzene release in cationic photoinitiators. Background technique [0002] In the past, people formulated cationic light-curing coatings, and widely used triarylsulfonium salt photoinitiators such as UVI6992. They produce simple phenyl compounds such as benzene after photolysis, which brings toxic residues to printed materials and may penetrate into the substrate. more serious problems in the packaging. Based on the non-toxic and environmental protection requirements in the field of food packaging, raw materials that produce volatile and easily migrated benzene-based small molecular substances will not be allowed to be used, prompting people to develop long-chain substituted phenylsulfonium salts as described in patent US4882201, or patented The biphenyl substituted sulfonium salt described in WO03 / 072567 that is allowed to appear in food, that is, 10-(4-biphenyl)...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D335/16
Inventor 杜西莹王永林闫庆金赵文超韩仕甸姚丽秀
Owner INSIGHT HIGH TECH (BEIJING) CO LTD
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