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Preparation method of acrylic acid-4-chlorobutyl ester compounds

A compound and chlorobutyl ester technology, applied in the field of preparation of acrylic acid-4-chlorobutyl ester compounds, can solve the problems of high price, inability to recycle, application limitation and the like, and achieve the effects of mild preparation reaction conditions and high yield

Inactive Publication Date: 2016-06-08
江苏优普生物化学科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the tetrahydrofuran ring-opening method reported in the literature, the commonly used catalyst is iodine simple substance, which is expensive and cannot be recycled, and its application is limited to a certain extent.

Method used

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  • Preparation method of acrylic acid-4-chlorobutyl ester compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Into a 1000ml four-necked round-bottomed flask equipped with mechanical stirring, thermometer and reflux condenser, add 173g tetrahydrofuran, 200g toluene, 10.9g zinc chloride, stir, heat up to 65°C, add 209g methacryloyl chloride dropwise, react for 5h . Gas chromatography detection (analysis conditions are: nitrogen as carrier gas, flow rate of 1.5mL / min., injection volume of 0.2 microliters; FID hydrogen flame ion detector, SEG30QC3 / AC5 column, gasification chamber temperature 280 ℃.) The reaction results showed that the raw material methacryloyl chloride was completely reacted, and the yield of the target product-4-chlorobutyl methacrylate reached 91.2%.

Embodiment 2

[0019] To a 1000ml four-necked round-bottomed flask equipped with mechanical stirring, a thermometer and a reflux condenser, add 216.3g of tetrahydrofuran and 22.5g of zinc bromide, stir, raise the temperature to 50°C, add 181g of acryloyl chloride dropwise, and react for 8h. The gas chromatography detection reaction results showed that the raw material acryloyl chloride was completely reacted, and the yield of the target product acrylic acid-4-chlorobutyl ester reached 94.5%.

Embodiment 3

[0021] To a 1000ml four-necked round-bottomed flask equipped with mechanical stirring, a thermometer and a reflux condenser, add 165.2g of tetrahydrofuran and 4.4g of zinc chloride, stir, raise the temperature to 60°C, add 135.8g of acryloyl chloride dropwise, and react for 4h. The gas chromatography detection reaction results showed that the raw material acryloyl chloride was completely reacted, and the yield of the target product 4-chlorobutyl acrylate reached 93.7%.

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Abstract

The invention discloses a preparation method of acrylic acid-4-chlorobutyl ester compounds. A catalyst is added to an organic solvent, acryloyl chloride or methacryloyl chloride is added dropwise, the mixture undergoes a ring-opening reaction for 0.5-10 h, and acrylic acid-4-chlorobutyl ester compounds are generated; the catalyst is a zinc salt compound. With the zinc salt compound such as zinc chloride, zinc bromide or zinc iodide as the catalyst, the preparation reaction condition is relatively mild, and the acrylic acid-4-chlorobutyl ester product can be obtained in a short time, and the yield of the acrylic acid-4-chlorobutyl ester product prepared with the method is higher and can be 90% or higher.

Description

technical field [0001] The invention relates to a preparation method of acrylic acid-4-chlorobutyl ester compound, and relates to the field of ring-opening reaction. Background technique [0002] 4-Chlorobutyl acrylate compound is a kind of important organic synthesis intermediate, this kind of compound has two active sites of carbon-carbon double bond and carbon-chlorine bond, and can interact with tertiary amines such as trimethylamine, dimethylethylamine, etc. The reaction generates cationic acrylate monomers containing quaternary ammonium salt structure, and can also prepare products such as liquid crystal materials containing aromatic structures, which have received extensive attention from many scientific researchers in recent years. [0003] However, there are many deficiencies in the traditional method for synthesizing acrylic acid-4-chlorobutyl ester compounds. Patent 200910253985.8 reported that p-toluenesulfonic acid was used as a catalyst, and acrylic acid and 6...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/24C07C69/653
CPCC07C67/24
Inventor 邹笑天曲红梅张继钱
Owner 江苏优普生物化学科技股份有限公司
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