Process for production of glycidyl ether compounds, and monoallyl monoglycidyl ether compound

Abstract

Provided are: a process by which a compound having an allyl ether linkage can be efficiently converted into the corresponding glycidyl ether compound under mild conditions using hydrogen peroxide as the oxidizing agent; and a novel monoallyl monoglycidyl ether compound having a biphenyl skeleton. Specifically provided are: a process for the production of glycidyl ether compounds which comprises reacting a compound having an allyl ether linkage with hydrogen peroxide to epoxidize the carbon-carbon double bond of the allyl group and thus form the corresponding glycidyl ether compound, characterized by using, as the reaction catalyst, a tungsten compound, a tertiary amine, and phenylphosphonic acid; and a monoallyl monoglycidyl ether compound having a biphenyl skeleton. The monoallyl monoglycidyl ether compound can be produced by the process.

Description

technical field [0001] The present invention relates to a method for producing a glycidyl ether compound and a monoallyl monoglycidyl ether compound. More specifically, the present invention relates to a feature characterized in that epoxidation is efficiently carried out by oxidizing the carbon-carbon double bond of the allyl group of a compound having an allyl ether bond with hydrogen peroxide using a predetermined catalyst. A method for producing a glycidyl ether compound, and a monoallyl monoglycidyl ether produced by oxidizing the carbon-carbon double bond of the allyl group of a compound having an allyl ether bond with hydrogen peroxide compound. Background technique [0002] Glycidyl ether known as a raw material of epoxy resins is industrially produced on a large scale and widely used in various fields. [0003] As a conventionally known method for producing glycidyl ether, there is a method in which corresponding alcohol or phenol is reacted with epichlorohydrin u...

AI Technical Summary

Problems solved by technology

This method requires a very large amount of tungsten compound to be used, and the speed of epoxidation is insufficient, so it cannot be implemented as an industrial manufacturing method

[0005] The following Patent Document 3 (US Patent No. 5,633,391 ) discloses that an olefin is brought into contact with bis(trimethylsilyl) peroxide as an oxidizing agent in an organic solvent in the presence of a rhenium oxide catalyst. method for epoxidation of alkenes, but requires expensive catalysts and oxidizing agents, and in the case of phenyl allyl ether, yields are insufficient

[0006] In the following Patent Document 4 (Japanese Patent Laid-Open No. 7-145221 ) and Patent Document 5 (Japanese Patent Laid-Open No. 58-173118 ), it is disclosed that phenol novolak resin is subjected to allyl ether through allyl halide. After oxidization, the method of epoxidation by peracid in an organic solvent requires the use of dangerous peracids

[0007] In addition, in the following Patent Document 6 (JP 2002-526483 A), it is disclosed that, in the presence of a titanium-containing zeolite catalyst, and a tertiary amine, a tertiary amine oxide, or a mixture thereof, hydrogen peroxide is used to carry out cyclization. The method of oxidation is useful in the case of an olefin compound with a small molecular weight as a substrate, but in the case of a substrate with a large molecular weight such as phenyl ether, the catalytic efficiency is poor and cannot be applied.

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