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ChemicalBook CAS DataBase List 2-(Perfluorobutyl)ethyl acrylate
52591-27-2

2-(Perfluorobutyl)ethyl acrylate synthesis

5synthesis methods

1H,1H,2H,2H-nonafluoro-1-hexanol (52.8 g) as fluoro alcohol and triethylamine (50 g) were dissolved in 500 ml of tetrahydrofuran. A solution of 18.1 g of acryloyl chloride as acid chloride in 100 ml of tetrahydrofuran was dropped in this solution over 2 hours while the mixture was being cooled in ice and stirred. After the completion of the dropping, the resulting white precipitate was filtrated and tetrahydrofuran and triethylamine were removed from the filtrate using a rotary evaporator. NMR measurement revealed that the resulting compound was 1H,1H,2H,2H-nonafluorohexyl acrylate.
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Yield:52591-27-2 92.2%

Reaction Conditions:

with toluene-4-sulfonic acid;hydroquinone at 80; for 5.5 h;Green chemistry;Reagent/catalyst;

Steps:

1.3; 3.3

(3) In the configuration of electromagnetic stirring, rectification column, thermometer, constant pressure dropping funnel,In a 2-liter reactor such as a separator or a condenser, 1000 g of an intermediate product (3.22 mol of a fluorine-containing alcohol), 8 g of p-toluenesulfonic acid, and 5 g of hydroquinone were added.The temperature was raised to 80 ° C with stirring, and 220 g (3.05 mol) of acrylic acid was added dropwise.The feeding time is 1.5 hours. At the end of the reaction, no significant water droplets were produced after 4 hours of continuous reaction. The fluorine-containing olefin and the unreacted fluoroalcohol are distilled off. The product was again distilled to 895 g of perfluorobutylethyl acrylate with a purity of 99.12% and a yield of 92.2%.

References:

CN108911983,2018,A Location in patent:Paragraph 0020; 0030

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