Method for preparing 1-ethylcyclohexyl acrylate

A cyclohexyl acrylate and ethyl technology, applied in the field of organic chemical synthesis, can solve the problems of complicated post-processing process, loss and the like, and achieve the effects of convenient industrial production, simple operation and high purity

Active Publication Date: 2015-09-16
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Both of the above two methods need to separate the 1-ethylcyclohexanol produced by the reaction before feeding in the next step. The post-treatment process is relatively cumbersome, and there will be a certain loss during the post-treatment process.

Method used

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  • Method for preparing 1-ethylcyclohexyl acrylate
  • Method for preparing 1-ethylcyclohexyl acrylate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Preparation of 1-ethylcyclohexyl acrylate: Weigh 6.2g (0.26mol) of magnesium chips into a 500ml three-neck flask and protect it with dry nitrogen. Weigh 32.0 g (0.296 mol) of bromoethane, 46.0 g of tetrahydrofuran and 60.0 g of toluene, mix them evenly, and place them in a constant pressure dropping funnel with an internal temperature of 13°C. Add 5mL of a mixture of tetrahydrofuran, toluene and ethyl bromide to the magnesium chips. After the reaction is initiated, a large amount of heat is released, and the internal temperature rises to 35°C. The solution turns gray and white smoke comes out. When the internal temperature dropped to 15°C, the mixture of ethyl bromide, tetrahydrofuran and toluene was continuously added dropwise and the stirring was started. Control the internal temperature to <35°C, drop it for 1 hour, then transfer to room temperature (20-30°C) and stir for 1 hour to prepare the Grignard reagent.

[0030] In addition, take 19.6g (0.2mol) cyclohexanone...

Embodiment 2

[0036] Preparation of 1-ethylcyclohexyl acrylate: Weigh 6.2g (0.26mol) of magnesium chips into a 500ml three-neck flask and protect it with dry nitrogen. Weigh 32.0 g (0.296 mol) of bromoethane and 86.0 g of tetrahydrofuran, mix them uniformly and place them in a constant pressure dropping funnel with an internal temperature of 13°C. Add 5 mL of a mixture of tetrahydrofuran and ethyl bromide to the magnesium chips. After the reaction is initiated, a large amount of heat is released, and the internal temperature rises to 35 ° C. The solution turns gray and white smoke comes out. When the internal temperature dropped to 15°C, the mixture of ethyl bromide and tetrahydrofuran was continuously added dropwise and the stirring was started. Control the temperature <35°C, drop it for 1h, then transfer to room temperature (20-30°C) and stir for 1 hour, no magnesium chips remain.

[0037] Take by weighing 19.6g (0.2mol) cyclohexanone and be dissolved in 20.0g toluene and be placed in th...

Embodiment 3

[0043]Preparation of 1-ethylcyclohexyl acrylate: Weigh 6.2g (0.26mol) of magnesium chips into a 500ml three-neck flask and protect it with dry nitrogen. Weigh 32.0 g (0.296 mol) of bromoethane, 46.0 g of tetrahydrofuran and 60.0 g of toluene, mix them evenly, and place them in a constant pressure dropping funnel with an internal temperature of 13°C. Add 5mL of a mixture of tetrahydrofuran, toluene and ethyl bromide to the magnesium chips. After the reaction is initiated, a large amount of heat is released, and the internal temperature rises to 35°C. The solution turns gray and white smoke comes out. When the internal temperature dropped to 15°C, the mixture of ethyl bromide, tetrahydrofuran and toluene was continuously added dropwise and the stirring was started. Control the internal temperature to <35°C, drop it for 1 hour, then transfer to room temperature (20-30°C) and stir for 1 hour to prepare the Grignard reagent.

[0044] Take by weighing 19.6g (0.2mol) cyclohexanone a...

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Abstract

The invention relates to a method for preparing 1-ethylcyclohexyl acrylate. The method comprises the following steps: magnesium turnings are fetched, and a mixed liquid of bromoethane and a reaction solvent is dropped into the magnesium turnings; bromoethane is subjected to a reaction with the magnesium turnings, such that a Grignard reagent is prepared; cyclohexanone is dissolved in toluene, and the solution is dropped into the Grignard reagent; when dropping is finished, a reaction is continued under a maintained temperature; when the Grignard reaction is finished, the temperature of the reaction system is reduced to 0-40 DEG C, and an acid-binding agent is added; a dichloromethane solution of propionyl chloride is dropped in, and an esterification reaction is carried out; when dropping is finished, the reaction is continued for 1-5h under a temperature maintained at 10-70 DEG C, such that a reaction liquid is obtained; the reaction liquid is poured into water for quenching; liquid separation is carried out; a water phase is extracted with dichloromethane; organic phases are combined; washing and drying are carried out, and the solvent is removed, such that a crude product is obtained; a polymerization inhibitor is added into a distillation flask, and the crude product is subjected to reduced-pressure distillation; and a distillate at a temperature of 98-100 DEG C under a pressure of 60Pa is collected, such that 1-ethylcyclohexyl acrylate is obtained. The method provided by the invention has the advantages of high yield, low cost, simple preparation, and suitability for expanded production. With the method, a GC purity can reach 99.5%. The method has a good application prospect.

Description

technical field [0001] The invention relates to a method for preparing 1-ethylcyclohexyl acrylate, which belongs to the field of organic chemical synthesis. Background technique [0002] In recent years, as semiconductor elements have been miniaturized, further miniaturization has been required in the photolithography steps of their production. Use the corresponding KrF, ArF or F 2 Various studies have been conducted on photolithography materials for short-wavelength irradiation light such as excimer lasers and methods for forming fine patterns, and development of new photolithography materials that can respond to short-wavelength irradiation light such as excimer lasers is expected. [0003] As photolithography materials, most of the materials developed in the past are based on phenolic resins. However, these materials contain aromatic rings and absorb light greatly, so they cannot obtain pattern accuracy sufficient to cope with miniaturization. [0004] Therefore, a poly...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/54C07C67/14
CPCC07C29/40C07C67/14C07C2601/14C07C69/54C07C31/1355
Inventor 马振堂李强易朝辉邹广辉秦三进刘志刚
Owner VALIANT CO LTD
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