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Method for preparing acetoacetoxy ethyl methacrylate

A technology of acetoacetoxyethyl methacrylate and hydroxyethyl methacrylate, which is applied in the field of preparation of acetoacetoxyethyl methacrylate, can solve problems such as difficult separation, low yield, and many side reactions, and achieve a solution Difficult separation, high yield, and the effect of improving product purity

Inactive Publication Date: 2016-05-04
WEIFANG KEMAI CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] U.S. Patent No. 3,554,987, US No. 3,658,878 once disclosed the synthetic method about AAEM, mostly adopt hydroxyethyl methacrylate (HEMA) and ethyl acetoacetate as raw material, carry out transesterification reaction with sulfuric acid as catalyst, these methods use ethyl acetate as solvent , due to the self-condensation and hydrolysis of ethyl acetoacetate, resulting in many side reactions and difficult separation, so the yield is low

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] 130g of hydroxyethyl methacrylate, 92g of toluene, 2g of sodium hydroxide as a catalyst, and 2g of hydroquinone as a polymerization inhibitor were added to the reaction flask after mixing, and the flask was placed in an oil bath at 100°C. When it reaches 90°C-100°C, add 90g of diketene dropwise into the flask for two hours. After the dropwise addition, keep it under the above temperature conditions for 6 hours. The solvent was distilled off at 120°C. After the solvent was removed, vacuum distillation was continued to collect fractions at a pressure of 150Pa and a temperature of 105°C-110°C. The 202g fraction obtained was acetoacetoxy ethyl methacrylate. The rate is 94%. The product is analyzed by gas chromatography. The main content is 98.5%, and the content of methacrylic acid is ≤0.5%.

Embodiment 2

[0023] Mix 130g of hydroxyethyl methacrylate, 100g of N,N-dimethylformamide, 2g of sodium hydroxide as a catalyst, and 2g of hydroquinone as a polymerization inhibitor, mix them into a reaction flask, and place the flask at 100°C In the oil bath, when the internal temperature reaches 90°C-100°C, add 110g of diketene dropwise into the flask for two hours. After the dropwise addition, keep it warm for 6 hours. Remove the solvent under the condition of 50°C-60°C, after removing the solvent, continue to carry out vacuum distillation, collect the fraction under the condition of pressure 200Pa and temperature 108°C-115°C, the obtained 202g fraction is acetoacetoxy ethyl methacrylate, The yield of the final product is 94%. The product is analyzed by gas chromatography. The main content is 98.6%, and the content of methacrylic acid is ≤0.5%.

Embodiment 3

[0025] 130g of hydroxyethyl methacrylate, 200g of chlorobenzene, 10g of triethylamine as a catalyst, 5g of phenothiazine and 5g of p-benzoquinone as a polymerization inhibitor were mixed and added to the reaction flask, and the flask was placed in a 130°C oil bath In the pot, when the internal temperature reaches 110°C-130°C, add 100g of diketene dropwise into the flask, the dropwise addition time is one hour, and keep warm for 3 hours after the dropwise addition is completed. The solvent was removed at -55°C, and after removing the solvent, distillation under reduced pressure was continued. Collect the fractions under the conditions of pressure 50Pa and temperature 100°C-105°C. The 206g fraction obtained is acetoacetoxyethyl methacrylate, and the yield of the final product is 95%. The product is analyzed by gas chromatography, and the main content is 98%. , Methacrylic acid content ≤ 0.5%.

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Abstract

The invention discloses a method for preparing acetoacetoxy ethyl methacrylate, which comprises the following steps: mixing hydroxyethyl methacrylate, a polymerization inhibitor, a catalyst and a solvent, and dropwisely adding ketene dimer at 30-160 DEG C; and after the dropwise addition is finished, carrying out thermal reaction under the temperature condition above until the reaction finishes; and after the thermal reaction finishes, distilling to remove the solvent, and continuing distillation to obtain the acetoacetoxy ethyl methacrylate. The method is simple in technique. The product has the advantages of high yield, high purity and stable quality.

Description

technical field [0001] The invention relates to a method for preparing acetoacetoxy ethyl methacrylate. Background technique [0002] Acetoacetoxyethyl methacrylate (AAEM) is a new type of methacrylic acid water-based functional monomer. It has the advantages of low toxicity, easy copolymerization and good complexation performance. Its special molecular structure makes AAEM in acrylic emulsion Polymerization, resin based on unsaturated polyester resin, UV light curing and other fields have a wide range of uses, and the application potential in industry is constantly expanding. Acetoacetoxy ethyl methacrylate (AAEM) is a light yellow transparent liquid , containing polymerizable vinyl and active acetoacetyl functional groups in the molecule, it is one of the new types of methacrylic monomers that have been studied internationally and have relatively high value. It has the characteristics of low toxicity and easy copolymerization. It has a wide range of uses in synthesis and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/46C07C67/54C07C69/72
CPCC07C67/46C07C67/54C07C69/72
Inventor 钟世强赵昱邢晓华刘存帅钟娟娟贾丽萍李远超
Owner WEIFANG KEMAI CHEM CO LTD
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