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Production method of epoxy compound and epoxy compound

A technology of epoxy compounds and manufacturing methods, applied in the direction of organic chemistry, etc., can solve the problems of easy runaway oxidation reaction, difficult organic solution wetting, unsuitable for removing quaternary salt compounds, etc.

Inactive Publication Date: 2017-06-27
ARAKAWA CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] In general, epoxy compounds are produced by oxidizing olefin compounds in the presence of an organic peroxide such as peracetic acid or performic acid, but this production method has the following problems: the organic peroxide is corrosive , the oxidation reaction is easily out of control, and by-products such as adducts of the organic peroxide remain in the resulting epoxy compound, etc.
[0007] However, these methods are all aimed at removing quaternary salt compounds contained in aqueous solutions, and are not suitable for removing quaternary salt compounds contained in organic solutions.
For example, if the aforementioned cyclodextrin aqueous solution is added to a solution of an organic solvent containing an epoxy compound and a quaternary salt compound, an emulsion is formed, and it is difficult or impossible to separate the quaternary salt compound.
In addition, ion exchange resins are generally hydrophilic and difficult to be wetted by organic solutions, so it is actually difficult to adsorb quaternary salt compounds contained in organic solutions

Method used

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  • Production method of epoxy compound and epoxy compound
  • Production method of epoxy compound and epoxy compound
  • Production method of epoxy compound and epoxy compound

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preparation example Construction

[0029] The preparation method of the present invention is characterized by comprising the following step 1, step 2 and step 3.

[0030] Step 1: After the olefin compound is oxidized in a mixed liquid composed of olefin compound, hydrogen peroxide solution, quaternary salt compound, heteropolyacid and organic solvent, the step of obtaining an organic solution (A) containing an epoxy compound ;

[0031] Step 2: After contacting the inorganic alkaline aqueous solution with the organic solution (A), the step of obtaining an organic solution (B) containing an epoxy compound;

[0032] Step 3: a step of obtaining an organic solution (C) containing an epoxy compound after contacting an acidic aqueous solution containing a polymer having at least one functional group selected from carboxyl and sulfonic acid groups with the organic solution (B).

[0033] Step 1 is a step of oxidizing and converting an olefin compound as a substrate into an epoxy compound.

[0034] As the olefin compou...

Embodiment 1

[0178]

[0179] To a test tube with a magnetic stir bar was added 2.34 g (24.4 mmol) of 35.5% by weight hydrogen peroxide solution, 123 mg (0.24 mmol) of methyl trioctyl ammonium chloride, 80 mg (0.24 mmol) of sodium tungstate dihydrate and 141 mg of (0.6 mmol) 42.5 weight% phosphoric acid aqueous solution was stirred at room temperature for 30 minutes, and the catalyst aqueous solution was prepared by this. Next, 2.69 g (12.2 mmol) of a diene compound represented by the following structure was added to the aqueous catalyst solution ( * 1) and 2.69 g of toluene, and carried out an oxidation reaction at 50° C. for 10 hours while stirring. After completion of the reaction, the organic phase in the aqueous phase and the organic phase separated into two layers is used as an organic solution (A). The residual amount of methyltrioctylammonium chloride in this organic solution (A) was 18053 ppm.

[0180]

[0181]

[0182] Add 4.40g of 2% aqueous solution of sodium hydroxide ...

Embodiment 2

[0187] In Example 1, the polymer aqueous solution P1 (4.90g) used in step 3 was replaced by the polymer aqueous solution P6 (4.90g), except that, the same operation was carried out to obtain the epoxy compound containing the above ( ** 1) The organic solution (C). The results are shown in Table 1.

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Abstract

The present invention relates to a method for producing an epoxy compound and an epoxy compound. The present invention provides a method for producing an epoxy compound with a small residual amount of the quaternary salt compound by removing the quaternary salt compound from an organic solution containing the epoxy compound and the quaternary salt compound. The manufacture method of epoxy compound of the present invention, it comprises following step 1, step 2 and step 3, step 1: in the mixed liquid that is made of olefin compound, hydrogen peroxide solution, quaternary salt compound, heteropolyacid and organic solvent After the olefin compound is oxidized, the step of obtaining the organic solution (A) containing the epoxy compound; step 2: after contacting the inorganic alkaline aqueous solution with the organic solution (A), obtaining the organic solution (A) containing the epoxy compound The step of solution (B); step 3: after contacting the acidic aqueous solution of the polymer having at least one functional group selected from carboxyl and sulfonic acid groups with the organic solution (B), the organic compound containing epoxy compound is obtained. Solution (C) step.

Description

technical field [0001] The present invention relates to a method for producing an epoxy compound using hydrogen peroxide, and an epoxy compound obtained by the production method. Background technique [0002] In general, epoxy compounds are produced by oxidizing olefin compounds in the presence of an organic peroxide such as peracetic acid or performic acid, but this production method has the following problems: the organic peroxide is corrosive , the oxidation reaction is easily out of control, and by-products such as adducts of the organic peroxide remain in the resulting epoxy compound. [0003] Therefore, a method of oxidizing olefinic compounds by using hydrogen peroxide instead of the aforementioned organic peroxides is being studied. In this production method, hydrogen peroxide as an oxidizing agent is not corrosive, the oxidation reaction is mild, and the by-product is only water, so it is industrially advantageous. [0004] However, it is difficult to oxidize olef...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D303/48C07D301/12C07D301/03C07D493/08C07D303/04C07D303/08
CPCC07D301/12
Inventor 笹川巨树内匠清惠崎阳一郎
Owner ARAKAWA CHEM IND LTD
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