JP7430503B2 - Manufacturing method of epoxy compound - Google Patents

Description

The present invention relates to a method for producing an epoxy compound and a composition containing the epoxy compound.

Epoxy compounds can be reacted with various curing agents and curing catalysts to form cured products that have high strength, excellent heat resistance, transparency, and the like. Therefore, it is extremely useful as a raw material for sealants, coating agents, adhesives, inks, sealants, etc.

As a method for producing such an epoxy compound, Patent Document 1 discloses that 1,3,5-tris(3-cyclohexenecarbonyloxy)cyclohexane is produced by reacting 1,3,5-cyclohexanetriol with cyclohexenecarboxylic acid chloride. A method is described in which 1,3,5-tris(3,4-epoxycyclohexanecarbonyloxy)cyclohexane is obtained by reacting the resulting compound with metachloroperbenzoic acid in the presence of a chlorinated solvent. There is.

Japanese Patent Application Publication No. 11-71363

However, with the above method, it is unavoidable that chlorine compounds are mixed into the epoxy compound. For example, if an epoxy compound mixed with chlorine compounds is used as a sealant for printed circuit boards, the chlorine compounds will cause the printed circuit board to The problem is that long-term reliability is reduced because the wiring (especially copper wiring) is corroded. Moreover, the above-mentioned problem is becoming more prominent as electronic components become smaller and more dense.

Therefore, an object of the present invention is to provide a method for efficiently producing 1,3,5-tris(3,4-epoxycyclohexanecarbonyloxy)cyclohexane with a low chlorine content.

As a result of intensive studies to solve the above problems, the present inventors obtained 1,3,5-tris(3-cyclohexenecarbonyloxy)cyclohexane (a compound represented by the following formula (2)) by utilizing a transesterification reaction. If the generated 1,3,5-tris(3-cyclohexenecarbonyloxy)cyclohexane is reacted with peracetic acid, 1,3,5-tris(3,4-epoxycyclohexanecarbonyloxy) can be efficiently produced. It was discovered that cyclohexane (an epoxy compound represented by the following formula (3)) can be produced, and since it is not necessary to use a chlorine compound in the reaction, an epoxy compound with a low chlorine content can be produced. The present invention was completed based on these findings.

（式（１）中、Ｒ¹はアルキル基を示す）
で表される化合物と、１，３，５－シクロヘキサントリオールとのエステル交換反応により、下記式（２）

で表される化合物を生成させる工程１と、
生成した前記式（２）で表される化合物に過酸を反応させて、下記式（３）

で表されるエポキシ化合物を得る工程２を含むエポキシ化合物の製造方法を提供する。 That is, the present invention is based on the following formula (1)

(In formula (1), R ¹ represents an alkyl group)
By the transesterification reaction between the compound represented by and 1,3,5-cyclohexanetriol, the following formula (2) is obtained.

Step 1 of producing a compound represented by
The generated compound represented by the above formula (2) is reacted with a peracid to form the following formula (3).

Provided is a method for producing an epoxy compound, which includes Step 2 of obtaining an epoxy compound represented by:

The present invention also provides a method for producing the epoxy compound, wherein the peracid is performic acid and/or peracetic acid.

The present invention also provides a method for producing the epoxy compound, wherein the reaction in Step 2 is carried out in the presence of an acetate-based solvent.

The present invention also provides a method for producing the epoxy compound, wherein the reaction in Step 1 is carried out in the presence of an alkali metal amide and/or an alkali alkali metal.

The present invention also provides a method for producing the epoxy compound represented by the formula (3), wherein the chlorine content of the epoxy compound is 1000 ppm or less.

（式（ｅ）中、Ｘは単結合又は連結基を示す）

The present invention also contains a compound represented by the following formula (e) and an epoxy compound represented by the following formula (3) in a ratio of the former/latter (weight ratio) in the range of 90/10 to 1/99. A composition is provided.

(In formula (e), X represents a single bond or a connecting group)

The present invention also provides the composition for transfer molding.

According to the method for producing an epoxy compound of the present invention, 1,3,5-tris(3,4-epoxycyclohexanecarbonyloxy)cyclohexane can be produced more efficiently than conventional methods.
Further, in the method for producing an epoxy compound of the present invention, there is no need to use a chlorine-containing compound such as a chlorine-based solvent, so the chlorine content of the obtained epoxy compound can be made to an extremely low value. Therefore, the epoxy compound can be suitably used as a encapsulation material for semiconductors, etc., and the semiconductor encapsulated using the epoxy compound suppresses corrosion of the wiring due to chlorine, and prevents corrosion of the wiring. The occurrence of wire breaks, insulation defects, etc. is suppressed.
Therefore, by using the epoxy compound obtained by the epoxy compound manufacturing method of the present invention, it is possible to realize further miniaturization, higher density, higher reliability, and longer life of electronic components.

（式（１）中、Ｒ¹はアルキル基を示す）
で表される化合物（＝化合物（１））と、１，３，５－シクロヘキサントリオールとのエステル交換反応により、下記式（２）

で表される化合物を生成させる工程１と、
生成した前記式（２）で表される化合物（＝化合物（２））に過酸を反応させて、下記式（３）

で表されるエポキシ化合物（＝化合物（３））を得る工程２を含む。 [Production method of epoxy compound]
The method for producing the epoxy compound of the present invention is represented by the following formula (1):

(In formula (1), R ¹ represents an alkyl group)
By the transesterification reaction between the compound represented by (=compound (1)) and 1,3,5-cyclohexanetriol, the following formula (2) is obtained.

Step 1 of producing a compound represented by
The generated compound represented by the formula (2) (=compound (2)) is reacted with peracid to form the following formula (3).

It includes step 2 of obtaining an epoxy compound (=compound (3)) represented by:

In formula (1), R ¹ represents an alkyl group. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a s-butyl group, a t-butyl group, a pentyl group, a hexyl group, and the like having 1 to 8 carbon atoms (preferably is a straight-chain or branched alkyl group of about 1 to 6, particularly preferably about 1 to 3).

(Step 1)
Step 1 is a step of producing a compound represented by the above formula (2) by transesterifying the above compound (1) with 1,3,5-cyclohexanetriol.

The amount of the compound (1) used is, for example, 3 to 7 mol, preferably 4 to 6 mol, per 1 mol of 1,3,5-cyclohexanetriol.

The transesterification reaction is preferably carried out in the presence of a strong basic catalyst. Examples of strong basic catalysts include alkali metal amides and alkyl alkali metals.

（式中、Ｍはアルカリ金属を示し、Ｒ²、Ｒ³は同一又は異なって、水素原子、アルキル基、又はトリアルキルシリル基を示す。Ｒ²、Ｒ³がアルキル基である場合、これらの基は互いに連結して隣接する窒素原子と共に環を形成していてもよい） The alkali metal amide is represented by the following formula (c1), for example.

(In the formula, M represents an alkali metal, and R ² and R ³ are the same or different and represent a hydrogen atom, an alkyl group, or a trialkylsilyl group. When ^{R 2} and R ³ are an alkyl group, these (The groups may be linked to each other to form a ring with adjacent nitrogen atoms)

M represents an alkali metal, such as Li, Na, K, and Cs.

Examples of the alkyl group for R ² and R ³ include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, hexyl group, decyl group, Examples include straight-chain or branched alkyl groups having about 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms, particularly preferably 1 to 3 carbon atoms) such as dodecyl group.

Examples of the trialkylsilyl group for R ² and R ³ include linear groups having about 1 to 20 carbon atoms (preferably 1 to 10, particularly preferably 1 to 3), such as trimethylsilyl and t-butyldimethylsilyl groups. or a branched alkyl group-substituted silyl group.

Examples of the ring that R ² and R ³ may be connected to each other to form with an adjacent nitrogen atom include a 5- to 6-membered ring containing a nitrogen atom as a heteroatom, such as a pyrrolidine ring or a piperidine ring. Examples include rings.

Examples of the alkali metal amide include lithium amide, lithium diisopropylamide, lithium 2,2,6,6-tetramethylpiperidine, and lithium hexamethyldisilazide. These can be used alone or in combination of two or more.

The alkyl alkali metal is represented by the following formula (c2), for example.
R ⁴ -M (c2)
(In the formula, M represents an alkali metal and R ⁴ represents an alkyl group)

M in formula (c2) is the same as M in formula (c1) above.

Examples of the alkyl group for R ⁴ include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, hexyl group, decyl group, dodecyl group, etc. Examples include straight-chain or branched alkyl groups having 1 to 20 carbon atoms (preferably 1 to 10, particularly preferably 1 to 5).

Examples of the alkyl alkali metal include methyllithium, n-butyllithium, sec-butyllithium, and t-butyllithium. These can be used alone or in combination of two or more.

Among the strong basic catalysts, alkali metal amides are preferred, and lithium amide is particularly preferred, since they are excellent in promoting the transesterification reaction.

The amount of the strong basic catalyst used is, for example, about 10 to 50 mol, preferably 15 to 35 mol, per 100 mol of the above compound (1).

The transesterification reaction is preferably carried out in the presence of a solvent. As the solvent, it is preferable to use a solvent with a boiling point of 140° C. or higher under normal pressure (that is, higher than the melting point of 1,3,5-cyclohexanetriol) to dissolve 1,3,5-cyclohexanetriol well. This is preferable because it allows for Further, it is preferable that the solvent is a hydrophobic solvent (ie, a low polarity solvent). Examples of such solvents include alcohols such as t-butyl alcohol; aliphatic hydrocarbons such as octane; alicyclic hydrocarbons such as cyclohexane; aromatic hydrocarbons such as toluene, xylene, and ethylbenzene; Examples include nitrile. These solvents may be used alone or in combination of two or more.

The amount of the solvent used is, for example, 1 to 10 times by weight, preferably 1 to 3 times by weight the total amount of the above compound (1) and 1,3,5-cyclohexanetriol.

The reaction temperature for the transesterification is, for example, 150 to 250°C, preferably 170 to 200°C. The reaction time is, for example, about 1 to 4 hours. The transesterification reaction may be carried out under normal pressure, reduced pressure or increased pressure. The atmosphere for the transesterification reaction is not particularly limited as long as it does not inhibit the reaction, and may be, for example, an air atmosphere, a nitrogen atmosphere, an argon atmosphere, or the like.

In addition, as ^the reaction progresses, R ¹ OH (R ¹ is the same as R 1 in the above formula (1)) is generated, but the generated R ¹ OH must be removed from the reaction system in order to proceed with the reaction. This is preferable for promoting progress.

After the transesterification reaction is completed, the reaction product is preferably neutralized with an acid and further washed with water.

After completion of the transesterification reaction, the obtained reaction product is separated by a separation method such as filtration, concentration, distillation, extraction, crystallization, adsorption, recrystallization, column chromatography, or a combination of these methods. Can be purified. Thereby, a compound represented by the above formula (2) is obtained.

(Step 2)
Step 2 is a step (epoxidation reaction step) in which the compound represented by the above formula (2) is reacted with a peracid to obtain the epoxy compound represented by the above formula (3).

The peracid is represented by the following formula (a), for example.
R ⁵ -C(=O)OOH (a)
(In the formula, R ⁵ represents a hydrogen atom or a hydrocarbon group)

The hydrocarbon group for R ⁵ includes an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a bonded group thereof.

The aliphatic hydrocarbon group is preferably an aliphatic hydrocarbon group having 1 to 20 carbon atoms, such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, s-butyl group, t- Alkyl groups having about 1 to 20 carbon atoms (preferably 1 to 10, particularly preferably 1 to 3) carbon atoms such as butyl group, pentyl group, hexyl group, decyl group, dodecyl group; vinyl group, allyl group, 1-butenyl group Alkenyl groups having about 2 to 20 carbon atoms (preferably 2 to 10, particularly preferably 2 to 3) carbon atoms; such as ethynyl groups, propynyl groups, etc.; Examples include alkynyl groups of the order of 3).

The alicyclic hydrocarbon group is preferably a 3- to 20-membered alicyclic hydrocarbon group, such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, etc. is a 3- to 15-membered, particularly preferably 5 to 8-membered) cycloalkyl group; a 3- to 20-membered (preferably 3 to 15-membered, particularly preferably 5 to 8-membered) cyclopentenyl group, cyclohexenyl group, etc. cycloalkenyl group; perhydronaphthalen-1-yl group, norbornyl group, adamantyl group, tricyclo[5.2.1.0 ^2,6 ]decane-8-yl group, tetracyclo[4.4.0.1 ^2,5 ． Examples include bridged cyclic hydrocarbon groups such as 1 ^7,10 ]dodecane-3-yl group.

The aromatic hydrocarbon group is preferably an aromatic hydrocarbon group having 6 to 14 carbon atoms (preferably 6 to 10 carbon atoms), such as a phenyl group, a naphthyl group, and the like.

Among the peracids represented by the above formula (a), examples of peracids in which R ⁵ is a hydrogen atom include hydrogen peroxide.

Among the peracids represented by the above formula (a), examples of the peracids in which R ⁵ is an aliphatic hydrocarbon group include performic acid and peracetic acid.

Among the peracids represented by the above formula (a), examples of the peracid in which R ⁵ is an aromatic hydrocarbon group include perbenzoic acid.

As the peracid, among the peracids represented by the above formula (a), peracids in which R ⁵ is an aliphatic hydrocarbon group (particularly performic acid and/or peracetic acid) may be used. However, it is preferable because it has excellent oxidizing power, does not require the use of a chlorine-based solvent as a solvent, and can suppress the mixing of chlorine-containing compounds into the target epoxy compound.

The amount of the peracid used is, for example, about 3 to 6 mol, preferably 3 to 4.5 mol, per 1 mol of the compound represented by formula (2).

The epoxidation reaction is preferably performed in the presence of a solvent. The solvent is preferably a hydrophobic solvent (ie, a low polarity solvent). Such solvents include, for example, aliphatic hydrocarbon solvents such as hexane, heptane, and octane; alicyclic hydrocarbon solvents such as cyclohexane; aromatic hydrocarbon solvents such as benzene, toluene, xylene, and ethylbenzene; Examples include chain or cyclic ether solvents such as ethyl ether and tetrahydrofuran; acetate ester solvents such as ethyl acetate. These solvents may be used alone or in combination of two or more.

Among these, it is preferable to use an acetate-based solvent as the solvent, since the boiling point under normal pressure is higher than the reaction temperature, and the boiling point is not too high, so it is easy to distill off and handle.

The amount of the solvent used is, for example, 1 to 10 times, preferably 2 to 5 times the weight of the compound represented by formula (2).

The reaction temperature of the epoxidation reaction is, for example, 20 to 50°C. The reaction time is, for example, about 0.5 to 12 hours. The transesterification reaction may be carried out under normal pressure, reduced pressure or increased pressure. The atmosphere for the epoxidation reaction is not particularly limited as long as it does not inhibit the reaction, and may be, for example, any of air atmosphere, nitrogen atmosphere, argon atmosphere, etc.

After the epoxidation reaction is completed, the reaction product is preferably washed with water and further neutralized with a base.

After the completion of the epoxidation reaction, the obtained reaction product is separated by a separation means such as filtration, concentration, distillation, extraction, crystallization, adsorption, recrystallization, column chromatography, or a combination of these. Can be separated and purified. This yields compound (3).

According to the method for producing an epoxy compound of the present invention, the transesterification reaction and the epoxidation reaction proceed rapidly to produce compound (3) in a high yield (the yield is, for example, 60% or more, preferably 70% or more, Particularly preferably 80% or more, most preferably 85% or more).

Compound (3) obtained by the method for producing an epoxy compound of the present invention has low volatility and is excellent in handleability. Further, by curing, a cured product with excellent heat resistance can be formed.

Moreover, according to the method for producing an epoxy compound of the present invention, an epoxy compound with a low chlorine content can be produced. The chlorine content is, for example, 1000 ppm or less, preferably 100 ppm or less, particularly preferably 10 ppm or less based on the total amount of the epoxy compound.

Since the epoxy compound obtained by the production method of the present invention has a low chlorine content as described above, it can be suitably used as a sealing material for printed circuit boards.

If the epoxy compound obtained by the manufacturing method of the present invention is used as a sealing material, the problem of corrosion of wiring due to chlorine will not occur, so electronic components can be further miniaturized, densified, and highly reliable. and a longer life can be achieved.

（式（ｅ）中、Ｘは単結合又は連結基を示す）

[Composition]
The composition of the present invention (for example, a curable composition) comprises a compound represented by the following formula (e) (=compound (e)) and an epoxy compound represented by the following formula (3) (=compound (3)). )).

(In formula (e), X represents a single bond or a connecting group)

(Compound (e))
Compound (e) in the present invention is a compound represented by the above formula (e). In formula (e), X represents a single bond or a connecting group. The cyclohexene oxide group in formula (e) may have a substituent, and examples of the substituent include a C _1-3 alkyl group.

Examples of the linking group include a divalent hydrocarbon group, an alkenylene group in which part or all of the carbon-carbon double bond is epoxidized, a carbonyl group (-CO-), an ether bond (-O-), Examples include an ester bond (-COO-), a carbonate group (-O-CO-O-), an amide group (-CONH-), and a group in which a plurality of these are linked.

Examples of the divalent hydrocarbon group include a linear or branched alkylene group having 1 to 18 carbon atoms, a divalent alicyclic hydrocarbon group having 3 to 18 carbon atoms, and the like. . Examples of the linear or branched alkylene group having 1 to 18 carbon atoms include a methylene group, a methylmethylene group, a dimethylmethylene group, an ethylene group, a propylene group, and a trimethylene group. Examples of the divalent alicyclic hydrocarbon group having 3 to 18 carbon atoms include 1,2-cyclopentylene group, 1,3-cyclopentylene group, 1,2-cyclohexylene group, and 1,3-cyclopentylene group. Examples include cycloalkylene groups such as cyclohexylene group and 1,4-cyclohexylene group.

Examples of the alkenylene group in which part or all of the carbon-carbon double bond is epoxidized (sometimes referred to as an "epoxidized alkenylene group") include a vinylene group, a propenylene group, and a 1-butenylene group. , 2-butenylene group, butadienylene group, pentenylene group, hexenylene group, heptenylene group, octenylene group, and other straight or branched alkenylene groups having 2 to 8 carbon atoms. In particular, the epoxidized alkenylene group is preferably an alkenylene group in which all of the carbon-carbon double bonds are epoxidized, more preferably an alkenylene group having 2 to 4 carbon atoms in which all of the carbon-carbon double bonds are epoxidized. It is an alkenylene group.

Examples of the compound represented by the above formula (e) include (3,4,3',4'-diepoxy)bicyclohexyl, bis(3,4-epoxycyclohexylmethyl)ether, 1,2-epoxy-1 , 2-bis(3,4-epoxycyclohexan-1-yl)ethane, 2,2-bis(3,4-epoxycyclohexan-1-yl)propane, 1,2-bis(3,4-epoxycyclohexane-1-yl) Examples include 1-yl)ethane and compounds represented by the following formulas (e-1) to (e-10). In addition, L in the following formula (e-5) is an alkylene group having 1 to 8 carbon atoms, and among them, a linear or A branched alkylene group is preferred. Furthermore, n ¹ to n ⁸ in the following formulas (e-5), (e-7), (e-9), and (e-10) each represent an integer from 1 to 30.

The weight ratio (former/latter) of the compound (e) and the compound (3) contained in the composition of the present invention is in the range of 90/10 to 1/99. , and in that a cured product with excellent heat resistance is obtained, the weight ratio is preferably 60/40 to 10/90, particularly preferably 50/50 to 10/90, and most preferably 40/60 to 20/90. It is 80. When the content of compound (e) is excessive, the viscosity of the composition at 100 to 150°C becomes too low, making it easy to leak out of the mold, and the leaked composition tends to form burrs. There is. The viscosity of the composition at 100 to 150° C. is preferably in the range of, for example, 100 to 2,500 mPa·s. Moreover, when the content of compound (e) becomes excessive, the heat resistance of the obtained cured product tends to decrease. On the other hand, if the content of compound (e) is too low, the viscosity of the composition tends to become too high, making it difficult to use it, for example, in transfer molding.

The viscosity of the composition of the present invention at 25° C. and a shear rate of 3.1 (1/s) is, for example, 500 to 32,000 mPa·s, and preferably 1,000 to 32,000 mPa·s in terms of ease of transfer molding. 32,000 mPa·s, particularly preferably 2,000 to 25,000 mPa·s, most preferably 2,000 to 10,000 mPa·s, particularly preferably 2,000 to 5,000 mPa·s. The viscosity of the slurry can be controlled by adjusting the blending ratio of the compound (e) and the compound (3).

The composition of the present invention may contain other components in addition to the compound (e) and the compound (3), such as a curing catalyst, a curing agent, a curing accelerator, and a solvent.

The amount of the curing catalyst used is, for example, about 0.1 to 3.0 parts by weight, preferably 0.3 to 1.5 parts by weight, based on the total of 100 parts by weight of the compound (e) and the compound (3). Parts by weight.

The amount of the curing agent used is, for example, about 80 to 130 parts by weight, based on the total of 100 parts by weight of the compound (e) and the compound (3).

The amount of the curing accelerator to be used is, for example, about 0.1 to 3.0 parts by weight, preferably 0.3 to 1.0 parts by weight, based on the total of 100 parts by weight of the compound (e) and the compound (3). 5 parts by weight.

The composition of the present invention can be prepared by blending and mixing the compound (e), the compound (3), and other components as needed.

The composition of the present invention can be subjected to heat treatment and/or light irradiation to advance the polymerization reaction of the compound (e) and the compound (3) contained in the composition to obtain a cured product. .

The cured product of the composition has excellent heat resistance, and the Tg (DMA-tan δ), that is, the peak top temperature of tan δ determined by dynamic mechanical analysis (DMA) measurement is, for example, 180°C or higher, preferably 200°C. The temperature is particularly preferably 210°C or higher. Further, Tg (TMA), that is, the inflection point of the coefficient of thermal expansion determined by TMA measurement, is, for example, 190°C or higher, preferably 200°C or higher, particularly preferably 210°C or higher, and most preferably 220°C or higher.

Moreover, if the compound (3) obtained by the above-described method for producing an epoxy compound is used, a composition with a low chlorine content can be obtained. When chlorine is contained in the composition, the epoxy groups of the compound (e) and the compound (3) are ring-opened by chlorine, making it difficult for the curing reaction to proceed. Although it is difficult to obtain, a composition with a low chlorine content can exhibit excellent curability and form a cured product with excellent heat resistance.

The chlorine content of the composition of the invention is, for example, 1000 ppm or less, preferably 100 ppm or less, particularly preferably 10 ppm or less.

The composition of the present invention can form a cured product having excellent heat resistance as described above. Therefore, the composition of the present invention is suitable as a raw material for producing, for example, a (transparent) sealing material for an optical semiconductor device, a light reflector, and the like.

EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples.

Example 1
In a 1L stainless steel reactor, 51.0 g of 1,3,5-cyclohexanetriol [manufactured by Tokyo Kasei Kogyo Co., Ltd.] and 275.9 g of methyl 3-cyclohexene-1-carboxylate [manufactured by Tokyo Kasei Kogyo Co., Ltd.] , 326.9 g of xylene, and 1.24 g of lithium amide [LiNH ₂ , manufactured by MERCK] were charged, and the temperature inside the reactor was raised to 190°C. Additionally, methanol distilled out during the reaction was removed.
The reaction solution thus obtained was diluted with 345 g of ethyl acetate and neutralized by adding 6.4 g of acetic acid. Thereafter, the reaction solution was washed with water, and the solvent of the reaction solution was distilled off to obtain 170.0 g of compound (2) (yield: 96%).
Next, 170.0 g of the obtained compound (2) was diluted with 510 g of ethyl acetate, and 364.1 g of 28% peracetic acid was added dropwise at 40° C. over 1 hour. After the dropwise addition was completed, the reaction was continued for 7 hours. The resulting reaction solution was washed with water and further neutralized with a 10% aqueous sodium hydroxide solution. Thereafter, the solvent was distilled off to obtain 177.8 g of compound (3) (yield: 95%). The chlorine content of the obtained compound (3) was below the detection limit (ie, below 10 ppm).

Example 2 (Preparation of composition)
Each component was blended according to the recipe shown in Table 1 below, mixed uniformly using a revolution-revolution type stirring device (trade name "Awatori Rentaro AR-250", manufactured by Thinky Co., Ltd.), and defoamed. A composition was obtained. The viscosity of the obtained composition at 25° C. and a shear rate of 3.1 (1/s) was 31,400 mPa·s.

The viscosity of the composition was measured using a rheometer (trade name "PHYSICA UDS200", manufactured by Anton Paar) at a temperature of 25° C. and a rotation speed of 186 rpm.

(Curing of composition)
The obtained composition was filled into a molding machine and heated at 80°C for 3 hours and then at 180°C for 2 hours to obtain a cured product. Then, the following heat resistance evaluation 1 of the cured product was performed on the obtained cured product.

Examples 3 to 4 (Example 4 is a reference example) , Comparative Example 1
A composition and a cured product thereof were obtained in the same manner as in Example 2 except that the formulation was changed as shown in Table 1 below, and the heat resistance of the obtained cured product was evaluated.

Example 5 (Preparation of composition)
Each component was blended according to the formulation shown in Table 2 below, mixed uniformly using a rotation-revolution stirring device, and defoamed to obtain a composition.

(Curing of composition)
The resulting composition was filled into a molding machine and heated at 100°C for 2 hours, then at 150°C for 2 hours, and further at 180°C for 1 hour to obtain a cured product. Moreover, the following heat resistance evaluations 1 and 2 of the cured product were performed on the obtained cured product.

Comparative example 2 (preparation of composition)
A composition and a cured product thereof were obtained in the same manner as in Example 5 except that the formulation was changed as shown in Table 2 below, and the heat resistance of the obtained cured product was evaluated.

(Evaluation of heat resistance of cured product 1)
A test piece with a size of 0.5 mm thickness x 8 mm width x 40 mm length was cut out from the obtained cured product. The peak top temperature of loss tangent (tan δ) (Tg (DMA-tan δ)) of the test piece was measured using a dynamic viscoelasticity measuring device (DMA) (manufactured by Seiko Instruments Inc.).
Note that the measurements were carried out under the following conditions.
Measurement atmosphere: Under nitrogen flow Measurement temperature range: -50 to 300℃
Heating rate: 2℃/min Deformation mode: Tensile mode

(Evaluation of heat resistance of cured product 2)
The glass transition temperature (Tg (TMA)) of the obtained cured product was measured using a TMA measurement device (trade name "TMA/SS100", manufactured by SII Nanotechnology) using a method based on JIS K7197. After measuring the thermal expansion coefficient in the measurement temperature range of 30 to 300 °C in an atmosphere at a heating rate of 5 °C/min, draw tangents to the curves below the glass transition temperature and above the glass transition temperature, and It was found from the intersection of
The coefficient of linear expansion (ppm/°C) below the glass transition temperature is α1, and the coefficient of linear expansion (ppm/°C) above the glass transition temperature is α2.

Celloxide 2021P: 3,4-epoxycyclohexylmethyl (3,4-epoxy)cyclohexanecarboxylate, SI-100L manufactured by Daicel Corporation: Curing catalyst, Rikacid MH700F manufactured by San-Apro Corporation: Curing agent, 4-methylhexahydro anhydride Phthalic acid/hexahydrophthalic anhydride = 70/30, manufactured by Shin Nippon Chemical Co., Ltd. U-CAT 12XD: Curing accelerator, manufactured by San-Apro Co., Ltd.

Claims (10)

The following formula (1)

(In formula (1), R ¹ represents an alkyl group)
By the transesterification reaction between the compound represented by and 1,3,5-cyclohexanetriol, the following formula (2) is obtained.

Step 1 of producing a compound represented by
The generated compound represented by the above formula (2) is reacted with a peracid to form the following formula (3).

A method for producing an epoxy compound, comprising step 2 of obtaining an epoxy compound represented by: The method for producing an epoxy compound according to claim 1, wherein the peracid is performic acid and/or peracetic acid. The method for producing an epoxy compound according to claim 1 or 2, wherein the reaction in step 2 is carried out in the presence of an acetate-based solvent. The method for producing an epoxy compound according to any one of claims 1 to 3, wherein the reaction in step 1 is carried out in the presence of an alkali metal amide and/or an alkyl alkali metal. The method for producing an epoxy compound according to any one of claims 1 to 4, wherein the epoxy compound represented by formula (3) has a chlorine content of 1000 ppm or less. A composition containing the following compound (e) and the following epoxy compound (3) in a former/latter ratio (weight ratio) in the range of 60/40 to 10/90 .
Compound (e): (3,4,3',4'-diepoxy)bicyclohexyl, bis(3,4-epoxycyclohexylmethyl)ether, 1,2-epoxy-1,2-bis(3,4-epoxy) cyclohexan-1-yl)ethane, 2,2-bis(3,4-epoxycyclohexan-1-yl)propane, 1,2-bis(3,4-epoxycyclohexan-1-yl)ethane, and the following formula ( At least one compound selected from the compounds represented by e-1) to (e-10)

(In the formula, L represents an alkylene group having 1 to 3 carbon atoms, and n ¹ to n ⁸ each represent an integer of 1 to 30.)
Epoxy compound (3): Compound represented by the following formula (3)

The composition according to claim 6, which has a viscosity of 2000 to 32000 mPa·s at 25° C. and a shear rate of 3.1 (1/s) . The composition according to claim 6 or 7 , which is used for transfer molding. The composition according to claim 6 or 7, which is a sealant. The composition according to any one of claims 6 to 8, which is a composition for forming a reflector.