Preparation technology of polyhalogenated aryl allyl ether compound

A technology for the preparation of aryl allyl ethers, which is applied in the direction of preparation of ethers by addition of unsaturated compounds, preparation of ethers, organic chemistry, etc., and can solve the problems of ineffective utilization of mother liquor, inability to recover reactants, and low reaction yields , to achieve high product yield, reduce production and preparation costs, and simple process

Active Publication Date: 2010-07-21
河南森远科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The object of the present invention is to provide a kind of technique simple, yield height, solvent can be recycled, the preparation technique of the polyhalogenated aryl allyl ether compound that no pollutant produces, this preparation technique has overcome the inability of mother liquor in the prior art Effective utilization, excess reactants cannot be recovered, and the defects of low reaction yield

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1 Put 0.03mol of tribromophenol, 0.033mol of sodium hydroxide, and 100ml of water into a 250ml three-neck reaction flask equipped with a thermometer, reflux condenser, and stirrer, heat to 80°C, and stir until it dissolves completely. Control the pH value at 10, add 20mg of tetrabutylammonium bromide, and continue stirring for 10 minutes; add 0.04mol 3-chloropropene dropwise at 45°C, and react for 60 minutes after the dropwise addition; heat at 55°C, and keep reflux for 6 hours. After the reaction is completed, cool to room temperature and filter, the filter cake is washed with water until neutral, and dried to obtain a light yellow solid product. The yield of tribromophenyl allyl ether is 80.2%, and the purity is relatively low.

Embodiment 2

[0025]Example 2 Add 0.03mol of tribromophenol, 80ml of 90% ethanol and 20ml of water to a 250ml there-necked flask equipped with a thermometer, a reflux condenser, and a stirrer, and the potassium hydroxide of 0.03mol is heated to 50°C. Stir until it is completely dissolved. Control the pH value at 10, add 0.5g of NaI, and continue to stir for 10 minutes; add 0.05mol 3-chloropropene dropwise at 45°C, and react for 60 minutes after the dropwise addition; heat at 80°C, and keep reflux for 5 hours. After completion of the reaction, cool to room temperature and filter, wash the filter cake with water until neutral, and dry to obtain an off-white solid product. The product yield is 85%.

Embodiment 3

[0026] Example 3 Put 0.03 mol of tribromophenol, 80 ml of methanol, and 0.03 mol of sodium methoxide into a 250 ml three-necked flask equipped with a thermometer, reflux condenser, and stirrer, heat to 40° C., and stir until it completely dissolves. Control the pH value at 11, add 0.1g of NaI, add 10mg of tetrabutylammonium bromide, and continue to stir for 10 minutes; dropwise add 0.045mol 3-chloropropene, after the dropwise addition, react for 30 minutes; keep the reflux temperature for 3 hours . After completion of the reaction, cool to room temperature and filter, wash the filter cake with water until neutral, and dry to obtain a white solid product. The product yield is 98%, and the purity of tribromophenyl allyl ether is relatively high.

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Abstract

This invention relates to a preparation technology of multi-halogenated aryl allyl group ether compounds. It takes multi-halogenated phenol and halogeno-propylene as raw materials, its characteristics is that the process include: take water as reaction solvents, dissolve multi-halogenated phenol by adding organic or inorganic alkali, multi-halogenated phenol and halogeno-propylene take reaction under catalyst; the described catalyst selected from the NaI ,KI, NaI and surfactant mixtures, or KI and surfactant mixtures; surfactant is quaternary ammonium surfactants, anionic surfactant or non-ionic surfactants. The invention provides a method of preparation simple, high-yield; and can recycling mother liquor, reducing production cost, thus good at general industrial applications while maintaining the requirements of environmental protection.

Description

technical field [0001] The invention relates to the preparation technology of halogenated aryl allyl ether compounds, in particular to a preparation method of polyhalogenated aryl allyl ether compounds. Background technique [0002] Polyhalogenated aryl allyl ether compounds are widely used in various fields. It can be used as a drug intermediate to synthesize the desired drug, and can also be used as a halogenated flame retardant with excellent performance. Polyhalogenated aryl allyl ether compounds will be widely used as flame retardants in FRP and expandable polystyrene manufacturing. [0003] The synthesis technology of aryl allyl compounds has been published in various publications in the form of literature in China, such as using acrylic acid as a raw material to react with thionyl chloride to obtain acryloyl chloride, acryloyl chloride and 2,4,6-tribromophenol in the presence of a catalyst The reaction generates tribromophenyl acrylate (Li Guofang, Liu Tieliang, the ...

Claims

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Application Information

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Patent Type & AuthorityPatents(China)
IPC IPC(8): C07C43/225C07C41/06
Inventor王彦林
Owner河南森远科技有限公司