Method for producing fluorine-containing alkyl (meth)acrylate

一种制造方法、丙烯酸的技术，应用在丙烯酸酯或甲基丙烯酸酯丙烯酸酯)的制造领域，能够解决无法完全预料反应等问题

Inactive Publication Date: 2008-03-12
TOKUYAMA CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0023] As mentioned above, it can be seen that the production method of fluorine-containing alkyl (meth)acrylate is a very specific reaction, and it is impossible to predict whether the reaction will proceed smoothly.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0130] Add 1 L of dichloromethane, 3,3,4,4,5,5,6,6,6-nonafluorohexanol 100 g (379 mmol), acrylic acid 30 g (417 mmol), and benzenesulfonate into a 3 L four-neck glass reactor. 73 g (414 mmol) of acid chloride, and 0.5 g of a polymerization inhibitor (manufactured by Sumitomo Chemical Co., Ltd., trade name: Smilizer GM). At this time, almost no heat generation of the reaction solution was observed.

[0131] Then, while cooling the reaction liquid to 40° C. or lower, 84 g (832 mmol) of triethylamine was slowly added dropwise. After completion of the dropwise addition, the reaction solution was further stirred at 30° C. for 3 hours. The resulting reaction mixture was subjected to gas chromatographic analysis. The conversion rate is above 99%, and the selectivity is 99%. 250 mL of water was added to the reaction mixture and stirred for 30 minutes. After standing still, the separated organic layer was extracted. Further, the organic layer was washed with 250 mL of water each t...

Embodiment 2

[0134] In a 5L four-neck glass reactor, add 3L of dichloromethane, 7g (69mmol) of triethylamine, 81g (764mmol) of sodium carbonate, 3,3,4,4,5,5,6,6,6-nine 100 g (379 mmol) of fluorohexanol and 0.5 g of Smilizer GM were added dropwise to 55 g (764 mmol) of acrylic acid. Next, 135 g (765 mmol) of benzenesulfonyl chloride was added dropwise while keeping the reaction temperature below 40°C. After completion of the dropwise addition, stirring was continued at 30° C. for 2 hours to obtain a reaction mixture. The conversion rate at this time was 88%, and the selectivity was 99%.

[0135] 400 mL of water was added to the reaction mixture, stirred for 1 hour, and then left to stand, and the organic layer separated from the water layer was extracted. Dichloromethane was distilled off under reduced pressure from the organic layer. 2 L of dichloromethane was added again to the obtained evaporation residue. Further, after adding 15 g (148 mmol) of triethylamine and 10 g (139 mmol) of ...

Embodiment 3

[0138]In a 200mL three-necked glass reactor, 80mL of dichloromethane, 10g (38mmol) of 3,3,4,4,5,5,6,6,6-nonafluorohexanol, 5g (58mmol) of methacrylic acid, 10 g (57 mmol) of benzenesulfonyl chloride, and 0.1 g of Smilizer GM as a polymerization inhibitor. Then, 12 g (119 mmol) of triethylamine was added dropwise while keeping the reaction temperature at 40° C. or lower. After completion of the dropwise addition, the mixture was stirred at room temperature for 1 hour. The conversion rate at this time was 99%, and the selectivity was 99%.

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PUM

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Abstract

Disclosed is a method for producing a fluorine-containing alkyl (meth)acrylate represented by the general formula (2) below. The method is characterized in that a fluorine-containing alcohol represented by the general formula (1) below, a (meth)acrylic acid and a sulfonic acid halide are reacted in the presence of a base containing at least one tertiary amine. Rf-(CH2)k-[-A-(CH2)l-]m-OH (1) (In the formula, Rf represents a perfluoroalkyl group having 1-21 carbon atoms; A represents S, SO or SO2; k represents 0, 1 or 2; l represents 1, 2 or 3; and m represents 0 or 1. In this connection, k = 0 and m = 0 do not occur at the same time. Rf-(CH2)k-[-A-(CH2)l-]m-OCOCR=CH2 (2) (In the formula, R represents a hydrogen atom or a methyl group.

Description

technical field [0001] The present invention relates to a method for producing acrylate or methacrylate (hereinafter, these compounds may be collectively referred to as (meth)acrylate). More specifically, the present invention relates to the production of (meth)acrylic acid having a specific chemical structure by reacting a fluorine-containing alcohol of a specific chemical structure with (meth)acrylic acid and a sulfonyl halide in the presence of a base containing at least a tertiary amine Fluorine-containing alkyl ester method. Background technique [0002] Conventionally, as a fluorine-containing alcohol (general formula (1) described in this specification Among them, the chemical structure corresponding to k=2 and m=0) reacts with (meth)acrylic acid to obtain these ester compounds, and the following methods are known. [0003] F(CF 2 CF 2 ) n CH 2 CH 2 OH(A) [0004] (In the formula, n represents an integer of 1 to 10.) [0005] A method of dehydrating a fluorin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C67/00C07C69/65
CPCC07C67/12C07C315/04C07C67/08C07C69/653C07C317/18
Inventor 山口真男山口史彦
Owner TOKUYAMA CORP
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