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Preparation method of 2-hydroxy-1-[4-(2-hydroxyethoxy) phenyl]-2-methyl-1-acetone

A hydroxyethoxy and phenyl technology, applied in the field of photoinitiator preparation, can solve the problems of catalyst loss, increased catalyst usage, loss of protective agent acetic acid, etc., and achieves the effect of high yield and purity

Pending Publication Date: 2022-04-12
TIANJIN JIURI NEW MATERIALS CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The prior art discloses a preparation method of a water-soluble photoinitiator 2-hydroxyl-1-[4-(2-hydroxyethoxyl)phenyl]-2-methyl-1-propanone, comprising using 2-hydroxyl Ethyl phenyl ether is used as a raw material. First, carry out a hydroxyl protection reaction with acetic acid, perform a Friedel-Crafts acylation reaction after vacuum distillation and purification, and obtain an alkyl-substituted aromatic ketone, and then carry out a bromination reaction in bromine carbon tetrachloride solution, and Alkaline hydrolysis in sodium methoxide methanol solution to obtain the above-mentioned photoinitiator (referring to literature: Sun Yong et al., Shandong Chemical Industry, 2003, (3): 5-9); CN102786405A and CN101811951A each disclose a kind of 2-hydroxyl-1- The preparation method of [4-(2-hydroxyethoxy) phenyl]-2-methyl-1-propanone all comprises: carrying out 2-hydroxyethyl phenyl ether acetate and isobutyryl chloride under Lewis acid catalysis Friedel-Crafts acylation reaction, followed by bromination and alkali hydrolysis to obtain the above-mentioned photoinitiator; the above-mentioned preparation process needs to protect and deprotect the hydroxyl group in the reaction raw material, resulting in a large loss of protective agent acetic acid; in addition, the Friedel-Crafts acylation process Among them, due to the presence of ester groups in the raw materials, a large amount of catalyst will be consumed, which will significantly increase the amount of catalyst used. Taking the amount disclosed in CN101811951A as an example, the amount of catalyst used is 2 to 2.2 times that of isobutyryl chloride. The theoretical dosage of chemical reaction is twice as high, resulting in a large loss of catalyst

Method used

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  • Preparation method of 2-hydroxy-1-[4-(2-hydroxyethoxy) phenyl]-2-methyl-1-acetone

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Embodiment 1

[0078] This embodiment provides a preparation method of 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methyl-1-propanone, which specifically includes the following steps:

[0079] (1) Add 94g of phenol, 84g of potassium hydroxide, 2g of PEG200 and 500g of dichloroethane in a four-neck flask to mix, heat up and reflux for dehydration reaction, GC monitors the conversion rate of phenol in the reaction solution > 98%, and then washes to neutral , reclaim ethylene dichloride by precipitation, and distill under reduced pressure to obtain the compound of formula b;

[0080]

[0081] The composition of the obtained compound of formula b was tested, and its liquid phase content was 98%, and the yield of the calculation step (1) was 94%;

[0082] The data result that the product obtained in step (1) is carried out to H-NMR analysis is as follows;

[0083] 1 H-NMR (CDCl3, 400Hz): 7.18-7.07 (m, 2H), 6.85-6.70 (m, 3H), 4.22 (t, 2H), 3.82 (t, 2H).

[0084] (2) Add the compound of formula...

Embodiment 2

[0097] The difference between this embodiment and Example 1 is only that in step (3), the equimolar amount of NaI is replaced by KI, and the equimolar amount and equal concentration of potassium hydroxide solution are replaced by sodium hydroxide solution. Other parameters and conditions and implementation Exactly the same as in Example 1.

[0098] The yield of photoinitiator 2959 in the step (3) of this embodiment is 85.7%, and the purity is 99.3%.

Embodiment 3

[0100] The difference between this embodiment and embodiment 1 is only that tetrabutylammonium bromide equimolar amount is replaced by tetrabutylammonium bisulfate, and other parameters and conditions are exactly the same as in embodiment 1.

[0101] The yield of photoinitiator 2959 in the step (3) of this embodiment is 83.0%, and the purity is 99.0%.

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Abstract

The invention relates to a preparation method of 2-hydroxy-1-[4-(2-hydroxyethoxy) phenyl]-2-methyl-1-acetone, which comprises the following steps: mixing 2-chloro-1-[4-(2-chloroethoxy) phenyl]-2-methyl-1-acetone with alkali liquor, alkali metal iodide and a phase transfer catalyst, and then carrying out microwave reaction to obtain the 2-hydroxy-1-[4-(2-chloroethoxy) phenyl]-2-methyl-1-acetone. The 2-hydroxyl-1-[4-(2-hydroxyethoxy) phenyl]-2-methyl-1-acetone is subjected to a reaction to obtain 2-hydroxyl-1-[4-(2- Alkali metal iodide and a phase transfer catalyst are added in the reaction process, microwave is combined, double hydrolysis of alpha-chlorine and alkyl chloride is achieved, the target photoinitiator is obtained, the alkaline hydrolysis reaction process has the high yield, the yield of 2-hydroxy-1-[4-(2-hydroxyethoxy) phenyl]-2-methyl-1-acetone can reach 80% or above, and the yield of 2-hydroxy-1-[4-(2-hydroxyethoxy) phenyl]-2-methyl-1-acetone can reach 80% or above. The purity can reach 99% or above.

Description

technical field [0001] The invention belongs to the field of photoinitiator preparation, and relates to a preparation method of 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methyl-1-propanone. Background technique [0002] 2-Hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methyl-1-propanone is a kind of α-hydroxy ketone photoinitiator, which has high photoinitiation efficiency and thermal Good stability, yellowing resistance, no peculiar smell; [0003] The prior art discloses a preparation method of a water-soluble photoinitiator 2-hydroxyl-1-[4-(2-hydroxyethoxyl)phenyl]-2-methyl-1-propanone, comprising using 2-hydroxyl Ethyl phenyl ether is used as a raw material. First, carry out a hydroxyl protection reaction with acetic acid, perform a Friedel-Crafts acylation reaction after vacuum distillation and purification, and obtain an alkyl-substituted aromatic ketone, and then carry out a bromination reaction in bromine carbon tetrachloride solution, and Alkaline hydrolysis in sodium me...

Claims

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Application Information

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IPC IPC(8): C07C45/64C07C45/46C07C45/63C07C49/84C07C41/16C07C43/225
Inventor 王晓蒙毛桂红赵国锋武瑞武锦鹏
Owner TIANJIN JIURI NEW MATERIALS CO LTD
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