JP2012025688A - Method for producing epoxy compound - Google Patents

Abstract

An object of the present invention is to provide a method for producing an epoxy-substituted isocyanurate by epoxidizing an olefin-substituted isocyanurate efficiently and under a mild condition in which side reactions and decomposition of a target product are sufficiently reduced and efficiently.
An epoxidation reaction is inactivated by using a catalyst system containing (1) an oxide salt of a Group VI element of the periodic table, (2) a surfactant, and (3) phosphoric acids and / or phosphonic acids. A method for producing an epoxy-substituted isocyanurate, comprising oxidizing an olefin-substituted isocyanurate with a hydrogen peroxide solution in an organic solvent to epoxidize at least one carbon-carbon double bond.
[Selection figure] None

Description

  The present invention relates to a novel method for producing isocyanurates having an epoxy group useful as an organic material.

  As a method for producing an isocyanurate having an epoxy group with high efficiency, an epichlorohydrin is allowed to act on cyanuric acid, and then an alkali metal chloride generated by dehydrochlorination with an alkali is separated to obtain 1,3,5-tris- ( Although a method for obtaining 2,3-epoxypropyl) -isocyanurate is known, epichlorohydrin easily reacts excessively and reacts with chlorohydrin before dehydrochlorination with an alkali to produce a chlorine-containing compound (see Patent Document 1). ). This reduction of the chlorine-containing compound requires an operation such as recrystallization and is difficult to remove completely. Naturally, the residue of these chlorine-containing compounds is also harmful to the use of electrical materials such as insulation performance, and causes performance degradation. In addition, this method has a limitation that the type of epoxide substituted on the nitrogen atom is only a 2,3-epoxypropyl group in terms of variations of the compound (see Patent Document 2).

  The method of producing an epoxy-substituted isocyanurate by epoxidizing an isocyanurate having an olefin by oxidation can increase the variation of the obtained epoxy compound, and is considered industrially useful without discharging a large amount of inorganic salt. It is done. In this case, a method for producing an epoxide by oxidizing an olefin substituted with isocyanurate is required.

  As a method for producing an epoxide by oxidizing an olefin, a method using a peroxide as an oxidizing agent such as a method using m-chloroperbenzoic acid or a method using peracetic acid is generally well known. However, these are not necessarily effective methods industrially because they discharge organic by-products equivalent to the product. In addition, peroxide has a problem in terms of safety.

On the other hand, hydrogen peroxide is inexpensive and non-corrosive, and the by-product after the reaction is harmless water. Therefore, it can be said to be an oxidizing agent that has a low environmental impact and is excellent for industrial use. .

As a method for producing an epoxy compound from olefins using hydrogen peroxide as an epoxidizing agent, (1) epoxy using a catalyst in which methyltrioxorhenium (CH ₃ ReO ₃ ) and a strong organic base compound are supported on an inorganic oxide is used. (Patent Document 3), (2) Epoxidation in the presence of an additive containing a titanium-containing zeolite catalyst and tertiary amine, tertiary amine oxide or a mixture thereof (Patent Document 4), (3) Fluoro A method of epoxidizing with an alkylketone catalyst (Non-patent Document 1) is known, but these methods (1) to (3) are high in catalyst cost and have poor catalyst efficiency and require excessive hydrogen peroxide. It is a method with many restrictions such as.

  As a method for producing an epoxy compound from an olefin using hydrogen peroxide as an epoxidizing agent and a catalyst of a Group VI element oxide having a relatively low catalyst cost as a catalyst, (4) Chloride 4 Epoxidation method in the presence of quaternary ammonium, phosphoric acid and tungsten metal salt (Patent Documents 5 and 6), (5) Epoxidation method in chloroform solvent using heteropolyacid cetylpyridinium salt as a catalyst (Non-Patent Documents) 2) is known. However, since a phase transfer catalyst containing a halogen atom or a halogen-based solvent, which is problematic in terms of environment and occupational health, is used, further improvement has been desired.

As a method of using hydrogen peroxide as an epoxidizing agent, using a salt of an oxide of a Group VI element of the periodic table with a relatively low catalyst cost as a catalyst, and not using a phase transfer catalyst containing a halogen atom or a halogen-based solvent. (6) A method of epoxidizing an organic solvent using a phase transfer catalyst such as a quaternary ammonium salt, tungstic acid and α-aminomethylphosphonic acid as a catalyst (Patent Document 7), (7) amine and 4th A method in which at least one quaternary ammonium salt, a tungsten compound, and α-aminomethylphosphonic acid are mixed and adjusted in an organic solvent for epoxidation (Patent Document 8), (8) a tungsten compound and hydrogen peroxide in a toluene solvent. A method of epoxidation in the presence of tungsten oxide, quaternary ammonium hydrogen sulfate and phosphoric acids which are reacted in advance (Patent Document 9) , It has been known. None of the methods (6) to (8) is supposed to be applied to the epoxidation reaction of a compound having an amide group in the molecule, and (7) and (8) are the adjustment of the catalyst itself or the reaction system. Adjustment of pH is complicated and unsuitable for mass synthesis.

Furthermore, although it is well known to produce epoxides from various fat-soluble olefins including cyclic and linear in the above-mentioned various methods, they are relatively high in polarity as isocyanurates substituted with olefins and produced. It has not been known about epoxidation of compounds that are easily hydrolyzed by epoxies.
Accordingly, there is a strong demand for the development of a method for producing epoxy-substituted isocyanurates with high efficiency and high selectivity from olefin-substituted isocyanurates with a simple operation and with high yield.

Japanese Patent Publication No. 48-24039 JP 2000-143661 A Japanese Patent Laid-Open No. 2001-25665 JP-T-2002-526383 JP 2003-192679 A JP 2004-115455 A JP-A-8-27136 JP 2009-256217 A JP 2004-59573 A

Chem. Commun. , 263-264 (1999) J. et al. Org. Chem. 53: 3587-3593 (1988)

  The present invention was made for the purpose of synthesizing an epoxy-substituted isocyanurate that is difficult to produce by the conventional techniques as described above, and can obtain an epoxy-substituted isocyanurate in a high yield under mild reaction conditions. Another object of the present invention is to provide a safe, simple and efficient process for producing an epoxy-substituted isocyanurate which can be easily performed and has a simple reaction operation and has very little influence and toxicity on the environment and the human body.

As a result of intensive studies to solve the above problems, the present inventors have epoxidized an olefin-substituted isocyanurate in an epoxidation reaction inert organic solvent, and more specifically, in an epoxidation reaction inert organic solvent. , Using hydrogen peroxide as an oxidizing agent, and using a mixed catalyst system containing an oxide salt of a Group VI element of the periodic table, a surfactant, and phosphoric acids and / or phosphonic acids. It has been found that by oxidizing a double bond, the corresponding epoxy-substituted isocyanurate can be produced safely and easily in a high yield, and hydrolysis of the resulting epoxide can be minimized, thereby completing the present invention. It came.

That is, this application provides the following invention.
A process for producing an epoxy-substituted isocyanurate that epoxidizes an olefin-substituted isocyanurate, specifically, an olefin-substituted isocyanurate and an aqueous hydrogen peroxide solution are mixed with aliphatic hydrocarbons, aromatic hydrocarbons, ethers, esters, amides, ketones, Or, in an epoxidation reaction inert organic solvent composed of a mixture thereof, the reaction is carried out in the presence of a mixed catalyst of a group VI element oxide salt, surfactant, phosphoric acid and / or phosphonic acid in the periodic table. A process for producing an epoxy-substituted isocyanurate characterized by

According to the method for producing an epoxy-substituted isocyanurate provided by the present invention, it is possible to produce a useful epoxy-substituted isocyanurate widely used as a solder resist ink or an LED sealant for electronic / optical materials under mild conditions, and Introduction of epoxy groups can be carried out with high selectivity and high yield at any ratio from 1 to 3 places.
In addition, since the production method of the present invention uses hydrogen peroxide as an oxidizing agent, the co-product is only water, has very little influence on the environment and the human body and toxicity, and has the effect of reducing the burden on the environment. An epoxy-substituted isocyanurate can be obtained safely, simply and efficiently.
From the above, the production method of the present invention is an invention that provides industrially advantageous effects.

  The present invention relates to a process for producing an epoxy-substituted isocyanurate by epoxidizing an olefin-substituted isocyanurate, and more specifically, (1) a salt of an oxide of a group VI element of the periodic table, It is characterized by reacting (oxidizing) with an aqueous hydrogen peroxide solution in the presence of (2) a surfactant and (3) a mixed catalyst system containing phosphoric acids and / or phosphonic acids.

〔式中、ｍ、ｐ、ｑはそれぞれ独立して同一又は相異なって１乃至４の数を表わし、ｎ、ｏ、ｒはそれぞれ独立して同一又は相異なって０乃至４の数を表わす。〕 The epoxy-substituted isocyanurate used as a raw material in the method of the present invention is an olefin-substituted isocyanurate represented by the following general formula (I).

[Wherein, m, p and q are independently the same or different and represent a number of 1 to 4, and n, o and r are independently the same or different and represent a number of 0 to 4. ]

In the general formula (1), m, p and q are each independently the same or different and represent a number of 1 to 4, and n, o and r are independently the same or different and are 0 to Since the number of 4 is represented, specific examples of the alkenyl group bonded to the N atom of the isocyanurate compound include 2-propenyl group, 2-butenyl group, 2-pentenyl group, 2-hexenyl group, 2-heptenyl group, 3-butenyl group, 3-pentenyl group, 3-hexenyl group, 3-heptenyl group, 3-octenyl group, 4-pentenyl group, 4-hexenyl group, 4-heptenyl group, 4
Examples include a linear alkenyl group such as an octenyl group, a 4-nonenyl group, a 5-hexenyl group, a 5-heptenyl group, a 5-octenyl group, a 5-nonenyl group, and a 5-decenyl group.

  In the present invention, various olefin-substituted isocyanurates represented by the general formula (1) can be used, and preferably 1,3,5-tris- (2-butenyl) -isocyanate. It is desirable to use nurate, 1,3,5-tris- (3-butenyl) -isocyanurate, 1,3,5-tris- (4-pentenyl) -isocyanurate.

  In the method for producing an epoxy-substituted isocyanurate of the present invention, an aqueous solution of hydrogen peroxide is used as an oxidizing agent. The amount of aqueous hydrogen peroxide used is usually 1.0 to 5.0 moles in terms of moles of hydrogen peroxide relative to the olefin (number of moles) of the olefin-substituted isocyanurates represented by formula (I), preferably Is in the range of 1.0 to 2.2 mole times. The concentration of the aqueous hydrogen peroxide solution is not particularly limited, and for example, a commercially available 30% by weight aqueous hydrogen peroxide solution can be used, or it may be diluted.

  Examples of the salt of the group VI element oxide include tungstate and molybdate, with tungstate being preferred.

  Tungstates are compounds that generate tungstate anions in water, such as tungstic acid (tungsten trioxide hydrate), tungsten trioxide, tungsten trisulfide, phosphotungstic acid, ammonium tungstate, potassium tungstate. Examples thereof include dihydrate and sodium tungstate dihydrate. Tungstic acid, tungsten trioxide, phosphotungstic acid, sodium tungstate dihydrate and the like are preferable. These tungstates may be used alone or in combination.

  The amount of group VI element oxide salt used in the periodic table is 0.0001 to 20 mol%, preferably 0.000, based on the olefin (number of moles) of the olefin-substituted isocyanurates represented by the formula (I). It is selected from the range of 01 to 10 mol%.

  Examples of the surfactant include anionic, cationic, zwitterionic and nonionic surfactants. The surfactant preferably used in the present invention is a quaternary ammonium salt containing no halide, and particularly preferably a hydrogen sulfate or a methyl sulfate.

  Examples of the quaternary ammonium salt containing no halide include tetrahexylammonium hydrogensulfate, tetra-n-octylammonium hydrogensulfate, methyltri-n-octylammonium hydrogensulfate, tetrabutylammonium hydrogensulfate, Examples include ethyl tri-n-octylammonium hydrogensulfate, cetylpyridiniumammonium hydrogensulfate, methyltri-n-octylammonium sulfate methylsulfate, tetrahexylammonium sulfate methylate, and bis (methyltrioctylammonium sulfate). Tetrahexyl ammonium hydrogen sulfate, methyl tri-n-octyl ammonium hydrogen sulfate, methyl tri-n-octyl ammonium hydrogen sulfate and the like are preferable. These quaternary ammonium salts may be used alone or in combination of two or more.

  The amount of the surfactant used is selected from the range of 0.0001 to 20 mol%, preferably 0.01 to 10 mol%, relative to the olefin (number of moles) of the olefin-substituted isocyanurates represented by the formula (I). It is.

Examples of phosphoric acids include phosphoric acid, sodium dihydrogen phosphate, disodium hydrogen phosphate, trisodium phosphate, polyphosphoric acid, and the like, and examples of phosphonic acids include phenylphosphonic acid, methylphosphonic acid, and α-amino acid. Examples include methylphosphonic acid, among which phosphoric acid and α-aminomethylphosphonic acid are preferable. These phosphoric acids and phosphonic acids may be used alone or in combination of two or more.

  The amount of phosphoric acid and / or phosphonic acid used is selected from the range of 0.0001 to 20 mol%, preferably 0.01 to 10 mol%, relative to the olefin (number of moles) of the olefin-substituted isocyanurates.

In the production method of the present invention, the olefin-substituted isocyanurate represented by the formula (I) is actually used as a hydrogen peroxide solution, an oxide salt of a VI element in the periodic table, a surfactant and phosphoric acid or It is carried out by reacting in an organic solvent inert to the epoxidation reaction in the presence of a mixed catalyst system containing phosphonic acids.
Although there is no restriction | limiting in particular in the epoxidation reaction inert organic solvent used at this time, The organic solvent comparatively inactive with respect to oxidation and a reduction reaction is preferable. Examples of the organic solvent include aliphatic hydrocarbons, aromatic hydrocarbons, ethers, esters, amides, ketones, and the like, and mixtures thereof.

  Specifically, pentane, hexane, heptane, octane, nonane, decane, cyclohexane, methylcyclohexane, 2,6-dimethylcyclooctane, benzene, toluene, xylene, mesitylene, ethylbenzene, cumene, diethyl ether, tert-butyl methyl ether , Acetone, 2-butanone, cyclohexanone, γ-butyrolactam, N, N-dimethylformamide, N, N-dimethylacetamide, ethyl acetate and the like. Of these, toluene and xylene are more preferable.

  The amount of the epoxidation reaction inert organic solvent is usually in the range of 0.01 to 200 times the mass number of the olefin-substituted isocyanurate represented by the formula (I), from the viewpoint of reactivity and operability. Is preferably in the range of 0.1 to 30 times by mass.

  In the production method of the present invention, the reaction conditions are not particularly limited, but the reaction is usually 5 to 100 ° C., preferably 30 to 90 ° C., more preferably 30 to 80 ° C., most preferably 30 to 60 ° C. Done in a range. The reaction pressure may be normal pressure, pressurization, or reduced pressure, but it is desirable to carry out the reaction at normal pressure.

  In the production method of the present invention, the reaction time can be appropriately determined in order to suppress a side reaction such as an epoxy hydrolysis reaction to a desired level. Usually, it is performed within 40 hours, preferably within 20 hours.

The epoxy-substituted isocyanurate obtained by the production method of the present invention is a compound represented by the following formula (II) to formula (IV). In the following formulae, m, p, q, and n, o, r represent the same meaning as previously defined in the compound represented by formula (I).

Specific examples of the compounds represented by the above formulas (II) to (IV) include 1,3,5-tris- (2,3-epoxybutyl) -isocyanurate, 1,3,5-tris- (3 , 4-epoxybutyl) -isocyanurate, 1,3,5-tris- (4,5-epoxypentyl) -isocyanurate, 1- (2,3-epoxybutyl) -3,5-bis- (2- Butenyl) -isocyanurate, 1,3-bis- (2,3-epoxybutyl) -5- (2-butenyl) -isocyanurate, 1- (3,4-epoxybutyl) -3,5-bis- ( 3-butenyl) -isocyanurate, 1,3-bis- (3,4-epoxybutyl) -5- (3-butenyl) -isocyanurate, 1- (4,5-epoxypentyl) -3,5-bis -(4-Pentenyl) -isocyanate Isocyanurate, 1,3-bis - (4,5-epoxy pentyl) -5- (4-pentenyl) - such as isocyanurate.
These compounds represented by the formula (II) to the formula (IV) are used in an amount of an aqueous hydrogen peroxide solution as an oxidizing agent, an amount of each component of the mixed catalyst system, and the above reaction conditions (temperature, pressure, reaction time). Etc.) can be adjusted at appropriate ratios.

The epoxy compound thus obtained quenches excess hydrogen peroxide used in the reaction. Therefore, after the reaction is completed, a reducing agent such as sodium bisulfite and sodium thiosulfate and sodium hydroxide, potassium hydroxide, potassium carbonate. It is desirable to treat with a base such as sodium carbonate.
By-products such as surfactants, hydrolysis products of epoxy, and coloring components in the obtained organic layer can be removed by a general method. For example, a method of adsorbing and removing with a metal oxide such as silica gel or activated carbon can be used. The method of use can be any of a method in which the adsorbent is dispersed in the solution and then filtration, and a method in which the adsorbent is spread on a column and the solution is passed through.

EXAMPLES Hereinafter, although an Example demonstrates this invention in detail, this invention is not limited at all by these Examples.
In the examples, the apparatus used for analyzing the samples is as follows.
· ¹ H NMR spectrometer: JEOL (Ltd.) JEOL-ECX400
・ HPLC
Device: GL-7400, manufactured by GL Sciences Inc.

<Example 1>
Sodium tungstate dihydrate (66.0 mg, 0.2 mmol), methyl tri-n-octylammonium sulfate methyl salt (48.0 mg, 0.1 mmol), toluene, 30 wt% aqueous hydrogen peroxide (1.077 g, 9.5 mmol), and an aqueous phosphoric acid solution is added and mixed so that the pH of the aqueous phase is about 2-3, and the temperature is adjusted to 60 ° C., and then 1,3,5-tris- (4-pentenyl) -isocyanate. Nurate (877.0 mg, 2.5 mmol) was added and allowed to react for 6 hours.
When the organic layer separated from the aqueous layer was analyzed by ¹ H NMR, the conversion of olefin was 95.
%, The epoxidation rate was 91%, and it was confirmed by HPLC analysis that the mixture was mainly of two types, and the yield of 1,3,5-tris- (4,5-epoxypentyl) -isocyanurate was The yield of 75% 1,3-bis- (4,5-epoxypentyl) -5- (4-pentenyl) -isocyanurate was confirmed to be 15%.

<Comparative Example 1>
In Example 1, the reaction was carried out without using sodium tungstate dihydrate. ¹
When analyzed by 1 H NMR, the epoxidation rate was 0%.

<Comparative example 2>
In Example 1, the reaction was carried out without using methyltri-n-octylammonium sulfate methyl salt. ^When analyzed by ¹ H NMR, the epoxidation rate was 0%.

<Comparative Example 3>
In Example 1, the reaction was carried out at a reaction temperature of 90 ° C. ^When analyzed by ¹ H NMR, the epoxidation rate was 0%.

<Comparative example 4>
In Example 1, the reaction was carried out without using an epoxidation reaction inert organic solvent. ¹ H N
When analyzed by MR, the epoxidation rate was 0%.

<Example 2>
Sodium tungstate dihydrate (66.0 mg, 0.2 mmol), methyl tri-n-octylammonium sulfate methyl salt (48.0 mg, 0.1 mmol), toluene, 30 wt% aqueous hydrogen peroxide (0.283 g, 2.5 mmol), and an aqueous phosphoric acid solution was added and mixed so that the pH of the aqueous phase was about 2-3, and the temperature was adjusted to 60 ° C., and then 1,3,5-tris- (4-pentenyl) -isocyanate. Nurate (877.0 mg, 2.5 mmol) was added and allowed to react for 4 hours.
When the organic layer separated from the aqueous layer was analyzed by HPLC, the conversion of 1,3,5-tris- (4-pentenyl) -isocyanurate was 68%, and mainly three kinds of mixtures were obtained. It was confirmed. The yield of each component was 43% for the yield of 1- (4,5-epoxypentyl) -3,5-bis- (4-pentenyl) -isocyanurate, 1,3-bis- (4,5
The yield of -epoxypentyl) -5- (4-pentenyl) -isocyanurate is 21% and the yield of 1,3,5-tris- (4,5-epoxypentyl) -isocyanurate is 4%. Was confirmed.

<Example 3>
Sodium tungstate dihydrate (66.0 mg, 0.2 mmol), methyl tri-n-octylammonium sulfate methyl salt (48.0 mg, 0.1 mmol), toluene, 30 wt% aqueous hydrogen peroxide (0.567 g, 5.0 mmol), and an aqueous phosphoric acid solution is added and mixed so that the pH of the aqueous phase is about 2-3, and the temperature is adjusted to 60 ° C., and then 1,3,5-tris- (4-pentenyl) -isocyanate. Nurate (877.0 mg, 2.5 mmol) was added and allowed to react for 4 hours.
When the organic layer separated from the aqueous layer was analyzed by HPLC, the conversion of 1,3,5-tris- (4-pentenyl) -isocyanurate was 86%, and mainly three kinds of mixtures were obtained. It was confirmed. The yield of each component was 36% for the yield of 1- (4,5-epoxypentyl) -3,5-bis- (4-pentenyl) -isocyanurate, 1,3-bis- (4,5- The yield of epoxypentyl) -5- (4-pentenyl) -isocyanurate is 36%, and the yield of 1,3,5-tris- (4,5-epoxypentyl) -isocyanurate is 14%. confirmed.

<Example 4>
In a test tube equipped with a magnetic stir bar, sodium tungstate dihydrate (39.6 mg, 0.12 mmol), methyl tri-n-octylammonium hydrogen sulfate (27.95 mg, 0.06 mmol), toluene, 30% by weight An aqueous hydrogen peroxide solution (888.0 g, 7.83 mmol) and an aqueous phosphoric acid solution were added so that the pH of the aqueous phase was about 2-3, and the temperature was adjusted to 60 ° C., and then 1,3,5-tris- ( 2-Butenyl) -isocyanurate (784.0 g, 2.61 mmol) was added and allowed to react for 6 hours.
As a result of analyzing the organic layer separated from the aqueous layer by HPLC, it was confirmed that the yield of 1,3,5-tris- (2,3-epoxybutyl) -isocyanurate was 69%.

<Example 5>
In a test tube equipped with a magnetic stir bar, sodium tungstate dihydrate (39.6 mg, 0.12 mmol), methyl tri-n-octylammonium sulfate methyl salt (48.0 mg, 0.1 mmol), toluene, 30.0 A weight% aqueous hydrogen peroxide solution (888.0 g, 7.83 mmol) and an aqueous phosphoric acid solution were added so that the pH of the aqueous phase was about 2-3, and the temperature was adjusted to 60 ° C., and then 1,3,5-tris -(2-Butenyl) -isocyanurate (784.0 g, 2.61 mmol) was added and allowed to react for 6 hours. The organic layer separated from the aqueous layer is ¹ H
According to NMR analysis, the epoxidation rate was 92%, and from the analysis by HPLC, the yield of 1,3,5-tris- (2,3-epoxybutyl) -isocyanurate was 69%, 1,3-bis- ( The yield of 2,3-epoxybutyl) -5- (2-butenyl) -isocyanurate was confirmed to be 23%.

<Example 6>
In Example 5, the reaction was carried out using ethyl acetate instead of toluene as the epoxidation reaction inert organic solvent. ^When analyzed by ¹ H NMR, the epoxy yield was 49%.

<Example 7>
Sodium tungstate dihydrate (66.0 mg, 0.2 mmol), methyl tri-n-octylammonium sulfate methyl salt (48.0 mg, 0.1 mmol), α-aminomethylphosphonic acid (11.23 mg, 0.1 mmol) , Toluene, a 30 wt% aqueous hydrogen peroxide solution (1.077 g, 9.5 mmol), and an aqueous phosphoric acid solution were added and mixed so that the pH of the aqueous phase was about 2-3, and the temperature was adjusted to 60 ° C. 1,3,5-Tris- (4-pentenyl) -isocyanurate (877.0 mg, 2.5 mmol) was added and allowed to react for 6 hours. When the organic layer separated from the aqueous layer was analyzed by ¹ H NMR, the conversion of olefin was 9
5%, epoxidation rate 90%, HPLC analysis confirmed to be mainly two kinds of mixtures, yield of 1,3,5-tris- (4,5-epoxypentyl) -isocyanurate Was found to be 76%, and the yield of 1,3-bis- (4,5-epoxypentyl) -5- (4-pentenyl) -isocyanurate was 12%.

Claims (6)

Olefin-substituted isocyanurates having three carbon-carbon double bonds represented by the following general formula (I)

[Wherein, m, p and q are independently the same or different and represent a number of 1 to 4, and n, o and r are independently the same or different and represent a number of 0 to 4. ]
An epoxidation reaction in an inert organic solvent consisting of aliphatic hydrocarbons, aromatic hydrocarbons, ethers, esters, amides, ketones, or mixtures thereof, at a reaction temperature of 30 to 80 ° C., A method for producing an epoxy-substituted isocyanurate represented by the following general formulas (II), (III) and (IV).

[Wherein, m, p and q are independently the same or different and represent a number of 1 to 4, and n, o and r are independently the same or different and represent a number of 0 to 4. ]

[Wherein, m, p and q are independently the same or different and represent a number of 1 to 4, and n, o and r are independently the same or different and represent a number of 0 to 4. ]

[Wherein, m, p and q are independently the same or different and represent a number of 1 to 4, and n, o and r are independently the same or different and represent a number of 0 to 4. ] In the epoxidation step, an aqueous hydrogen peroxide solution as an oxidizing agent, and (1) a salt of an oxide of a Group VI element of the periodic table, (2) a surfactant, and (3) phosphoric acids and / or as a catalyst The epoxy-substituted isocyanate according to claim 1, characterized in that a mixed catalyst system containing phosphonic acids is used to epoxidize at least one carbon-carbon double bond in the olefin-substituted isocyanurate represented by formula (I). A method for producing nurate. 3. The method for producing an epoxy-substituted isocyanurate according to claim 2, wherein the salt of the oxide of (1) Group VI element of the periodic table is a tungstate. The method for producing an epoxy-substituted isocyanurate according to claim 2, wherein the surfactant (2) is a quaternary ammonium salt. The method for producing an epoxy-substituted isocyanurate according to claim 4, wherein the quaternary ammonium salt is hydrogen sulfate or methyl sulfate. The method for producing an epoxy-substituted isocyanurate according to claim 2, wherein the (3) phosphoric acid and / or phosphonic acid is phosphoric acid or α-aminomethylphosphonic acid.