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Preparation method of 1-ethylcyclohexylmethacrylate

A technology of acrylate and cyclohexyl, which is applied in the field of preparation of substituted acrylate, can solve the problems of side reaction extraction, insufficient, difficult to remove by-products, etc., and achieve the effects of reducing the introduction of impurities, removing interference, and improving yield

Inactive Publication Date: 2019-06-14
NINGBO NATA OPTO ELECTRONICS MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this acidification process, side reactions and insufficient extraction are prone to occur, resulting in product loss and a decrease in yield
2. When the first method uses methacryloyl chloride as a raw material, the excess acid chloride will introduce impurities, and chlorine will also remain in the subsequent resin synthesis, affecting the performance of the photoresist
3. When the second method uses methacrylic acid as a raw material, the by-products of DCC are difficult to remove, and large-scale production cannot be realized
4. Although the third method does not require post-processing to obtain the intermediate alcohol in the first step, it still needs to use a format reagent, which is costly, and at the same time uses methacryloyl chloride as a raw material, which will still produce residual chloride ions

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation of 1-ethylcyclohexyl (meth)acrylate:

[0037]

[0038] Weigh 34.3g (1.4mol) of magnesium chips, 10g (0.06mol) of zinc chloride and 100g of diethyl ether in a 2L three-necked flask and pass through dry nitrogen protection. Weigh 222.4g (2.04mol) of bromoethane, 100g (1.02mol) of cyclohexanone and 500g of diethyl ether and mix them evenly to form a preparation solution I, which is placed in a constant pressure dropping funnel with an internal temperature of 32°C. Add 5mL of preparatory solution I to the magnesium chips. After the reaction is initiated, a large amount of heat is released, and the internal temperature rises to 60°C. The solution turns gray and white smoke comes out. When the internal temperature drops to 40°C, start adding the preparatory solution I dropwise and start stirring. Control the internal temperature <65°C, after 1 hour of dripping, keep the temperature at 40°C for 2 hours. Add 8.96g (0.08mol) of potassium tert-butoxide and 10g of...

Embodiment 2

[0040] Example 2: Preparation of 1-ethylcyclohexyl (meth)acrylate:

[0041]

[0042] Weigh 34.3g (1.4mol) of magnesium chips, 10g (0.04mol) of lanthanum chloride and 100g of diethyl ether in a 2L three-necked flask and pass through dry nitrogen protection. Weigh 222.4g (2.04mol) of bromoethane, 100g (1.02mol) of cyclohexanone and 500g of diethyl ether and mix them evenly to form a preparation solution I, which is placed in a constant pressure dropping funnel with an internal temperature of 32°C. Add 5mL of preparatory solution I to the magnesium chips. After the reaction is initiated, a large amount of heat is released, and the internal temperature rises to 60°C. The solution turns gray and white smoke comes out. When the internal temperature drops to 40°C, start adding the preparatory solution I dropwise and start stirring. Control the internal temperature <65°C, after 1 hour of dripping, keep the temperature at 40°C for 2 hours. Add 8.96g (0.08mol) of potassium tert-but...

Embodiment 3

[0044] Example 3: Preparation of 1-ethylcyclohexyl (meth)acrylate:

[0045]

[0046] Weigh 34.3g (1.4mol) of magnesium chips, 4g (0.09mol) of lithium chloride and 100g of diethyl ether into a 2L three-necked flask and pass through dry nitrogen protection. Weigh 222.4g (2.04mol) of bromoethane, 100g (1.02mol) of cyclohexanone and 500g of diethyl ether and mix them evenly to form a preparation solution I, which is placed in a constant pressure dropping funnel with an internal temperature of 32°C. Add 5mL of preparatory solution I to the magnesium chips. After the reaction is initiated, a large amount of heat is released, and the internal temperature rises to 60°C. The solution turns gray and white smoke comes out. When the internal temperature drops to 40°C, start adding the preparatory solution I dropwise and start stirring. Control the internal temperature <65°C, after 1 hour of dripping, keep the temperature at 40°C for 2 hours. Add 8.96g (0.08mol) of potassium tert-butoxi...

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Abstract

The invention discloses a preparation method of 1-ethylcyclohexylmethacrylate. The preparation method comprises following steps: bromoethane, Cyclohexanone, and magnesium chips are subjected to reaction in the presence of a first catalyst, after reaction, a second catalyst and a polymerization inhibitor are added directly, and a methyl acrylic anhydride solution is added dropwise for esterification reaction so as to obtain 1-ethylcyclohexylmethacrylate. According to the preparation method, in the first step, the catalyst is adopted for activation of ketone carbonyl groups, so that grignard reaction is more complete; in the second step, an intermediate is subjected to a next step of reaction without separation purification, so that the yield is increased greatly. It is shown by experimentsthat, 1, reaction total yield is as high as 90%; 2, an acid anhydride is adopted to take the place of acyl chloride for ester interchange reaction, so that introduction of impurities under other conditions is reduced, using of acyl chloride is avoided, and interference caused by chloride ions in products is avoided.

Description

technical field [0001] The invention relates to a preparation method of a compound, in particular to a preparation method of a substituted acrylate. Background technique [0002] As the size of integrated circuits continues to decrease, the resolution requirements for photoresists in the photolithography process are also increasing. This has prompted people to continue to conduct in-depth research on photoresist materials based on short-wavelength light sources such as KrF, ArF or F2 excimer lasers, and continue to develop photoresists with smaller line widths, higher resolutions, and smaller line roughness. glue material. As the current mainstream high-end photoresist material, due to the limitation of the light source used, ArF photoresist will absorb a large amount of phenolic resin containing benzene rings and cannot be used any longer. Through research, it is found that (meth)acrylates with ring structure, such as 1-alkylcyclohexyl (meth)acrylates, have no absorption ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/54C07C67/08
Inventor 许东升马潇周浩杰顾大公毛智彪沈博
Owner NINGBO NATA OPTO ELECTRONICS MATERIAL CO LTD