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Production method of fluorine-containing (methyl) acrylate monomer

A production method and acrylate technology are applied in the production field of fluorine-containing acrylate monomers, which can solve the problems of high production cost, low yield, environmental pollution and the like, and achieve the effects of less environmental pollution, environmental protection and production cost reduction.

Inactive Publication Date: 2012-07-11
太仓中化环保化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among the three methods, the hydrolysis of acyl chloride and alcoholysis of acryloyl chloride has serious environmental pollution problems, and the yield is low, only 60-70%; the most ideal p-toluenesulfonic acid is used as a catalyst in the direct esterification synthesis method , the esterification rate can only reach about 80%.
So far, the production of fluorine-containing (meth)acrylates has not reached a fully mature industrialization level in my country, and the production cost is high, which greatly limits the development and application of fluorine-containing polymers

Method used

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  • Production method of fluorine-containing (methyl) acrylate monomer
  • Production method of fluorine-containing (methyl) acrylate monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] A tetrafluoropropyl acrylate (structural formula: CH 2 =CH-COOCH 2 CF 2 CF 2 The preparation method of H) is specifically as follows: in a 250ml three-necked flask, add 39.6g tetrafluoropropanol, 64.5g methyl acrylate, 4.5g phenothiazine, 3.96g phosphotungstic acid (H 3 PW 12 O 40 .7H 2 O) and 100ml benzene. Stir and heat to 70°C, react for 12h, and end the reaction. After the reaction solution is cooled to 30°C, wash with warm water, collect the 132~134°C fraction under normal pressure to obtain tetrafluoropropyl acrylate product with a content of about 99.5% by weight. The yield is 75 %.

Embodiment 2

[0022] A tetrafluoropropyl acrylate (structural formula: CH 2 =CH-COOCH 2 CF 2 CF 2 The preparation method of H) is specifically as follows: in a 2.5L three-necked flask, add 396g of tetrafluoropropanol, 645g of methyl acrylate, 3.2g of phenothiazine, 12.9g of hydroquinone, 4.5g of p-hydroxyanisole, 39.6 g Phosphotungstic heteropoly acid (H 3 PW 12 O 40 .20H 2 O) and 1000ml of benzene. Stir and heat to 70°C. After 12 hours of reaction, the reaction is finished. After the reaction solution is cooled to 30°C, it is washed with distilled water. The fraction from 132 to 134°C is collected under normal pressure to obtain 521 g of tetrafluoropropyl acrylate with a purity of 99.5% and a yield of 93.2%. . The residue after distillation was filtered to obtain 39.2 g of recovered phosphotungstic heteropoly acid.

Embodiment 3

[0024] A method for producing 1,1,5-trihydroperfluoropentyl methacrylate, specifically: in a 500ml four-neck round bottom flask, add 116.2g octafluoropentanol, 60.1g methyl methacrylate, 0.31 g phenothiazine, 0.61g hydroquinone, 0.31g p-hydroxyanisole, 5.81g phosphotungstic acid (H 3 PW 12 O 40 .7H 2 O) and 140ml of benzene, heated to 80°C, kept at this temperature for 7 hours, and then finished the reaction. After the reaction solution was cooled to 30°C, washed with distilled water, distilled under reduced pressure, and collected 80°C / 23mmHg fractions to obtain a purity of 99.5 % 1,1,5-trihydroperfluoropentyl methacrylate 137.4g, the yield was 91.3%. The residue after distillation was filtered to obtain 5.77 g of recovered phosphotungstic heteropoly acid.

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Abstract

The invention relates to a production method of a fluorine-containing (methyl) acrylate monomer, which comprises a step that (methyl) acrylate reacts with fluorine-containing alcohol to produce fluorine-containing acrylate, wherein the reaction is carried out at the temperature of 50 DEG C-250 DEG C under the existence of phosphotungstic heteropoly acid, a polymerization retarder and an entrainer, and the charging molar ratio of the (methyl) acrylate to the fluorine-containing alcohol is 1.2-2.0:1. The invention uses the (methyl) acrylate and the fluorine-containing alcohol as raw materials and prepares the fluorine-containing (methyl) acrylate monomer through the alcoholysis reaction of the ester; the yield can reach as high as 96%; and the substances used in the reaction, such as the phosphotungstic heteropoly acid and the entrainer can be recycled and reused, so the production cost is greatly reduced. In addition, the method of the invention has little environment pollution and is beneficial to environment protection.

Description

Technical field [0001] The invention relates to a production method of fluorine-containing (meth) acrylate monomer. Background technique [0002] Fluorine-containing (meth)acrylate monomer is a fluorine-containing organic compound with double bonds, and is one of the important monomers of fluoropolymers. [0003] There are three main methods for synthesizing fluorine-containing (meth)acrylate monomers (see Zhang Qinghuai et al. Synthesis and application of fluorine-containing (meth)acrylate monomers, Acrylic Chemicals and Applications, Volume 18, Issue 2) , 21-25, 2005). Among the three methods, both the amidation method and the alcoholysis method of acryloyl chloride have serious environmental pollution problems, and the yield is low, only 60-70%; the direct esterification synthesis method uses the most ideal p-toluenesulfonic acid as the catalyst At this time, the esterification rate can only reach about 80%. So far, the production of fluorine-containing (meth)acrylate has not...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/653C07C67/03B01J31/18
Inventor 周旺鹰张超宋芬王恩来戴柏凡钱林
Owner 太仓中化环保化工有限公司