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Preparation method of 2-methyl-2-(4-morpholinyl)-1-[4-(methylthio)phenyl]-1-acetone

A technology of methylthio and morpholino, applied in the field of preparation of 2-methyl-2-(4-morpholino)-1-[4-(methylthio)phenyl]-1-propanone, It can solve the problems of unfriendly odor and low yield of the final product, and achieve the effect of low cost, high purity and easy operation

Active Publication Date: 2011-11-16
湖南久日新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This process also has problems such as low yield and unfriendly odor of the final product

Method used

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  • Preparation method of 2-methyl-2-(4-morpholinyl)-1-[4-(methylthio)phenyl]-1-acetone
  • Preparation method of 2-methyl-2-(4-morpholinyl)-1-[4-(methylthio)phenyl]-1-acetone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1: Preparation of 2-chloro-2-methylpropionyl chloride

[0022] 30 g (0.34 mol) of isobutyric acid and 26 g (0.17 mol) of phosphorus oxychloride were mixed, heated to 75° C. and reacted for 1.5 h. Chlorine gas was introduced into the reaction solution and stirred for 20h. It was distilled under reduced pressure (pressure 20KPa) to obtain 43.2 g of 2-chloro-2-methylpropionyl chloride. Yield: 90%, content 97%.

[0023] Boiling point: 90-91°C (pressure 20KPa).

[0024] 1 HNMR (CDCl 3 ): δ 1.60 (s, 6H).

Embodiment 2

[0025] Example 2: Preparation of 2-chloro-2-methylpropionyl chloride

[0026] 30 g (0.34 mol) of isobutyric acid and 23.4 g (0.17 mol) of phosphorus trichloride were mixed, heated to 70° C. and reacted for 1.5 h. Chlorine gas was introduced into the reaction solution and stirred for 20h. It was distilled under reduced pressure (pressure 20KPa) to obtain 41.2 g of 2-chloro-2-methylpropionyl chloride. Yield: 86%, content is 97%.

Embodiment 3

[0027] Example 3: Preparation of 2-methyl-2-chloro-1-[4-(methylthio)phenyl]-1-propanone

[0028] 120 mL of dichloromethane was cooled to 5°C in an ice-water bath, 16.8 g (0.126 mol) of aluminum trichloride was added, 16.0 g (0.113 mol) of 2-chloro-2-methylpropionyl chloride was slowly added dropwise for 20 min, and 11.3 g (0.113 mol) of 2-chloro-2-methylpropionyl chloride was slowly added dropwise g (0.091 mol) anisole for 30 min. Heat to 50°C and stir for 1.5h. The reaction solution was cooled to 20° C., added to 120 mL of 10% industrial hydrochloric acid, and stirred for 1 h. After standing, the aqueous layer was separated, the organic phase was washed with water until neutral, and dried over anhydrous sodium sulfate for 10 h. Precipitate at low pressure to obtain 17.5 g of pale yellow oil, which is 2-methyl-2-chloro-1-[4-(methylthio)phenyl]-1-propanone. Yield: 85%, content: 95%.

[0029] 1 H NMR (CDCl 3 ) δ 1.62 (s, 6H), 2.47 (s, 3H), 7.22 (d, 2H), 7.79 (d, 2H).

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Abstract

The invention a preparation method of 2-methyl-2-(4-morpholinyl)-1-[4-(methylthio)phenyl]-1-acetone. The 2-methyl-2-(4-morpholinyl)-1-[4-(methylthio)phenyl]-1-acetone prepared by the method provided by the invention is an efficient radical ultraviolet initialtor and is suitable for the single-function or multifunctional monomer ultraviolet curing system and an acrylate prepolymer. The compound can be used alone or used together with photo initiators (ITX and 184). As the compound has efficient ultraviolet absorption property, the compound is especially suitable for being used in the formulas of oil and colored paint such as offset ink, silk screen printing ink and printing plate-making photoresist. The method has the advantages of simple processing equipment, easiness for operation and low cost; the prepared compound has high purity; and the product purity reaches more than 99%.

Description

Technical field [0001] The invention relates to a method for preparing a high-efficiency free radical photoinitiator 2-methyl-2-(4-morpholinyl)-1-[4-(methylthio)phenyl]-1-propanone. Background technique [0002] 2-Methyl-2-(4-morpholinyl)-1-[4-(methylthio)phenyl]-1-propanone is a high-efficiency UV photoinitiator, suitable for single and multi-functional monomer UV Light-curing systems and acrylate prepolymers. There are currently five main methods for synthesizing this compound. Ciba-Geigy's patent EP0088050 reports that using anisole sulfide as raw material, the obtained methylthioisobutyl ketone is brominated, and the target product is obtained through the ring-opening reaction of the epoxy intermediate and morpholine. The patent CN1354175A of Beijing Yingli High-tech Technology Development Co., Ltd. reports that using anisole sulfide as the raw material, the obtained methylthioisobutyl ketone is brominated, and reacts with morpholine in the presence of a Lewis acid cat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/104
Inventor 赵国锋罗想张齐毛桂红郑勇王昆杨天艳李晓娟李欢欢
Owner 湖南久日新材料有限公司
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