Synthesis method of photoinitiator 1-hydroxycyclohexyl phenyl ketone

A technology of hydroxycyclohexyl phenyl ketone and cyclohexyl benzophenone, which is applied in the field of synthesis technology of 1-hydroxy cyclohexyl phenyl ketone, and achieves the effects of high yield, less waste water and high yield

Inactive Publication Date: 2020-11-20
UNIV OF SCI & TECH LIAONING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The purpose of the present invention is to provide a kind of synthetic method of photoinitiator 1-hydroxycyclohexyl phenyl ketone in order to overcome the technical problem that existing α-hydroxycyclohexyl phenyl ketone synthetic method exists

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Add 5.3g of magnesium powder, 70ml of tetrahydrofuran and a catalytic amount of iodine to a reactor with a condenser, heat up to 85°C and reflux, dropwise add 25g of chlorobenzene to initiate. After the Grignard reagent is prepared, 20g of cyclohexylcarbonitrile dissolved in 20ml of tetrahydrofuran is added dropwise. After the dropwise addition is completed, reflux at 85°C for 30min to 60min until the liquid phase detection reaction is complete. Cool to 25°C, then add a mixed acid solution of 22ml concentrated sulfuric acid and 50ml water. Stir at room temperature for 2 hours, separate liquids and evaporate to dryness under reduced pressure to obtain 33.5 g of cyclohexyl benzophenone with a yield of 97% and a liquid phase purity of 96%+.

[0029] Add 15 g of cyclohexyl benzophenone to a reactor with a condenser, and pass chlorine gas to react for 1.5 hours at 70°C to obtain 17.74 g of compound 1-chlorocyclohexyl benzophenone with a liquid phase purity of 98%+, and then add...

Embodiment 2

[0031] Add 5.3g of magnesium powder, 70ml of tetrahydrofuran and a catalytic amount of iodine to a reactor with a condenser, heat up to 85°C and reflux, dropwise add 35g of bromobenzene to initiate. After the Grignard reagent is prepared, 20g of cyclohexylcarbonitrile dissolved in 20ml of tetrahydrofuran is added dropwise. After the dropwise addition is completed, reflux at 80°C for 30min-60min until the liquid phase detection reaction is complete. Cool to 25°C, then add a mixture of 25ml concentrated sulfuric acid and 50ml water. Stir at room temperature for 2 hours, separate liquids and evaporate to dryness under reduced pressure to obtain 33.8 g of cyclohexyl benzophenone with a yield of 98% and a liquid phase purity of 96%+.

[0032] Add 15g of cyclohexyl benzophenone to the reactor with condenser, and let chlorine gas flow for 1.5 hours at 70℃ to obtain 17.8g of compound 1-chlorocyclohexyl benzophenone with a liquid phase purity of 98%+, then add 15ml In an aqueous solution...

Embodiment 3

[0034] Add 5.3g of magnesium powder, 70ml of tetrahydrofuran and a catalytic amount of iodine to a reactor with a condenser. The temperature is raised to 85°C to reflux, and 45g of iodobenzene is added dropwise to initiate. After the Grignard reagent is prepared, 20g of cyclohexylcarbonitrile dissolved in 20ml of tetrahydrofuran is added dropwise. After the dropwise addition is completed, reflux at 83°C for 30min to 60min until the liquid phase detection reaction is complete. Cool to 25°C, then add a mixture of 28ml concentrated sulfuric acid and 60ml water. Stir at room temperature for 2 hours, separate liquids and evaporate to dryness under reduced pressure to obtain 34.1 g of cyclohexyl benzophenone with a yield of 99% and a liquid phase purity of 96%+.

[0035] Add 15g of cyclohexyl benzophenone to a reactor with a condenser, and pass chlorine gas to react for 1.5 hours at 70℃ to obtain 17.9g of compound 1-chlorocyclohexyl benzophenone with a liquid phase purity of 98%+, and ...

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PUM

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Abstract

The invention aims to solve the technical problems of an existing alpha-hydroxycyclohexyl phenyl ketone synthesis method, provides a synthesis method of a photoinitiator 1-hydroxycyclohexyl phenyl ketone, and belongs to the technical field of chemical synthesis. The synthesis method comprises the following steps: (1) reacting a halogenated benzene with magnesium particles to prepare a Grignard reagent, dropwise adding cyclohexylcarbonitrile into the prepared Grignard reagent, and after the reaction is completed, hydrolyzing to generate cyclohexyl phenyl ketone; and (2) reacting cyclohexyl phenyl ketone with chlorine to obtain 1-chlorocyclohexyl phenyl ketone, and carrying out a hydrolysis reaction on the 1-chlorocyclohexyl phenyl ketone and a sodium hydroxide aqueous solution under the action of a catalyst to obtain 1-hydroxycyclohexyl phenyl ketone. The method is simple in synthesis process, high in yield and suitable for industrial production.

Description

Technical field [0001] The invention belongs to the technical field of chemical synthesis, and specifically relates to a synthesis process of 1-hydroxycyclohexyl phenyl ketone. Background technique [0002] Photoinitiator 184 is an efficient free radical type I non-yellowing photoinitiator, which is widely used in copy varnish, plastic coating wood coating, adhesive, lithographic printing ink, screen printing ink, flexo printing ink, and electronic products. [0003] At present, the following methods are mainly used for the synthesis of α-hydroxycyclohexyl phenyl ketone: [0004] (1) Felkin, Verrier; Journal of Bulletin of the Chemistry Society of France, 1967, 3: 1047-1052 reported that cyclohexanone and hydrogen cyanide were mixed to produce cyanohydrin, and dihydropyran was used to protect the hydroxyl group. It reacts with phenyl magnesium bromide and acid hydrolysis, the yield is about 30%. In this synthetic route, the step of removing the protective group needs to be carried ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/64C07C49/83
CPCC07C45/455C07C45/63C07C45/64C07C2601/14
Inventor 王永飞刘清雷
Owner UNIV OF SCI & TECH LIAONING
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