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Method for synthesizing 2-methyl-1-[4-(methylthio)phenyl]-2-(4-morpholinyl)-1-propanon

A synthetic method and morpholinyl technology are applied in the field of synthesis of 2-methyl-2-(4-morpholinyl)-1-[4-(methylthio)phenyl]-1-acetone, capable of Solve the problems of ineffective dissolution, high raw material price, and low product purity, and achieve the effects of low production cost, easy access to raw materials, and simple operation

Active Publication Date: 2010-03-03
INSIGHT HIGH TECH (BEIJING) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When methyl mercaptan is used instead of 2-hydroxyethanethiol for etherification, only a small amount of the target product is produced; the reason for the analysis is that the boiling point of methyl mercaptan is 11°C, and the methyl mercaptan introduced at the above reaction temperature quickly volatilizes to form a foul odor gas that does not dissolve effectively in solution
[0021] In summary, the existing preparation methods all have disadvantages such as high cost caused by high raw material prices, or low product purity due to unavoidable side reactions.

Method used

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  • Method for synthesizing 2-methyl-1-[4-(methylthio)phenyl]-2-(4-morpholinyl)-1-propanon
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  • Method for synthesizing 2-methyl-1-[4-(methylthio)phenyl]-2-(4-morpholinyl)-1-propanon

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Experimental program
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Embodiment 1

[0030] Embodiment 1: the preparation method of 2-methyl-2-(4-morpholinyl)-1-[4-(methylthio)phenyl]-1-propanone

[0031] 30g (0.112mol) 2-methyl-2-(4-morpholinyl)-1-(4-chlorophenyl)-1-propanone, 30ml toluene, 117g (0.336mol) of 20% sodium methylthiolate aqueous solution, Tetrabutylammonium bromide 1.1g (0.0034mol) was added to a 250mL reaction flask in turn, stirred and heated, and 2-methyl-2-(4-morpholinyl)-1-(4-chlorophenyl) was detected after 8h - The content of 1-acetone is 0.5%, stop heating, put it aside, add 50ml of toluene to the system, stir and separate, the organic phase is washed with water until it is nearly neutral, and then concentrated, and the residue is dissolved and crystallized with 75g of methanol to obtain 29.88g of the product. The rate is 95%. Analysis melting point 74~76℃, elemental analysis C15H12NO2S: C 64.47% (theoretical value 64.48%) H 7.60% (theoretical value 7.58%) N 5.06% (theoretical value 5.01%) S 11.50% (theoretical value 11.48%)

Embodiment 2

[0032] Embodiment 2: the preparation method of 2-methyl-2-(4-morpholinyl)-1-[4-(methylthio)phenyl]-1-propanone

[0033] 30g (0.112mol) 2-methyl-2-(4-morpholinyl)-1-(4-chlorophenyl)-1-propanone, 20% sodium methyl mercaptide aqueous solution 43.2g (0.123mol), tetrabutyl 5.4 g (0.0168 mol) of ammonium bromide was successively added to a 100 mL reaction flask, stirred and heated, and 2-methyl-2-(4-morpholinyl)-1-(4-chlorophenyl)-1 was detected after 8 hours. -The acetone content is 0.1%, stop the reaction, after standing, add 50ml chlorobenzene to the system, stir and separate layers, the organic phase is washed with water until it is near neutral and then concentrated, the obtained crude product is recrystallized with 75g ethanol to obtain 30.8g of the product, the yield 98%.

Embodiment 3

[0034] Embodiment 3: the preparation method of 2-methyl-2-(4-morpholinyl)-1-[4-(methylthio)phenyl]-1-propanone

[0035] 30g (0.112mol) 2-methyl-2-(4-morpholinyl)-1-(4-chlorophenyl)-1-propanone, 78g (0.224mol) of 20% sodium methylthiolate aqueous solution, tetraoctyl Add 4.9g (0.009mol) of ammonium bromide to a 250mL reaction flask in turn, stir and heat, and analyze 2-methyl-2-(4-morpholinyl)-1-(4-chlorophenyl)-1- The remaining 0.3% of acetone stopped the reaction. After standing, 50ml of toluene was added to the system, and the layers were stirred. The organic phase was washed with 50ml of water until it was nearly neutral and then concentrated. The obtained crude product was recrystallized with 75g of methanol to obtain 30.2g of the product, with a yield of 96 %.

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Abstract

The invention relates to a method for synthesizing a high-efficiency photoinitiator 2-methyl-1-[4-(methylthio)phenyl]-2-(4-morpholinyl)-1-propanon. In the method, 2-methyl-1-[4-(chloro)phenyl]-2-(4-morpholinyl)-1-propanon serving as a raw material is reacted with sodium methyl mercaptide in an organic water two phase solution system taking quaternary ammonium salt as a catalyst to generate the target product.

Description

Technical field: [0001] The invention relates to a method for synthesizing 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 (Formula I) is a high-efficiency UV photoinitiator, suitable for single and poly Functional monomer UV curing system and acrylate prepolymer. Can be used alone or mixed with ITX, 184. Due to its high UV absorption, it is especially suitable for use in ink and paint formulations. Such as offset printing ink, screen ink, printing plate photoresist, etc. [0003] [0004] Formula I [0005] At present, there are mainly four processes for synthesizing this compound. The first one is the patent EP0088050 of Ciba-Geigy Company. Using sulfide anisole as raw material, the obtained methylthio isobutyl ketone is brominated, and the target is obtained by reacting the cyclized product with morpholine. pro...

Claims

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Application Information

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IPC IPC(8): C07D295/104
Inventor 赵文超闫庆金文成贵麻忠利王永林任杰
Owner INSIGHT HIGH TECH (BEIJING) CO LTD
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