JPH04266878A - Production of epoxy group-containing compound - Google Patents

Abstract

PURPOSE:To industrially and advantageously obtain the subject compound by reacting a specific double bond-containing compound with an oxygen-containing gas in the presence of a manganese compound and an aldehyde compound. CONSTITUTION:A compound expressed by formula I [R<1> is H, alkyl, etc.; R<2> and R<3> are H, (substituted) alkyl, etc., provided that R<1> and R<3> may mutually be bound to form a rung and R<1>, R<2> and R<3> may simultaneously be bound to form a condensed ring] is reacted with an oxygen-containing gas (e.g. pure oxygen or air) in the presence of one or more selected from compounds expressed by formulas II, III and IV (R<4> and R<6> are lower alkyl, aryl, etc., R<5> is H, halogen, etc.; R<4> and R<5> may mutually be bound to form a rind; X is halogen, ClO4<->, etc.), etc., and a compound expressed by the formula R<14> CHO (R<14> is alkyl or aryl which may have a substituent group), preferably at 20-50 deg.C under preferably 0.2-2.0atm to afford the objective compound expressed by formula V. The above-mentioned compounds are preferably used in amounts based on 1mol compound expressed by formula I as follows. 0.0096-4mol% compound expressed by formula II, etc., and 1-10mol% aldehyde compound.

Description

Detailed Description of the Invention [0001] [Industrial Application Field] The present invention relates to a method for producing an epoxy group-containing compound, and in particular, the present invention relates to a method for producing an epoxy group-containing compound. This invention relates to a method for obtaining a compound. [0002] Conventionally, as a method for producing an epoxy group-containing compound, a compound having a double bond is mixed in an inert solvent such as benzene, chloroform, or carbon tetrachloride.
A method of oxidizing with an organic peroxide such as perbenzoic acid, performic acid, perphthalic acid, perpropionic acid, perbutyric acid, or trifluoroperacetic acid is known. In particular, industrially, peracetic acid is produced by adding a strong acid catalyst to a mixture of a substance that produces peroxide, such as glacial acetic acid, and an unsaturated compound, and adding hydrogen peroxide while heating the mixture to 60 to 70°C. A method of producing an epoxy group-containing compound using this peracetic acid has been carried out. [0003] However, since the reaction in the above method is a sensitive reaction, it is difficult to carry out the epoxidation reaction selectively, and moreover, it is difficult to carry out the epoxidation reaction selectively. As a result, a part of the generated epoxy group-containing compound may polymerize. Moreover, since this reaction is carried out under severe reaction conditions at a reaction temperature of 50° C. or higher, side reactions are likely to occur, making it impossible to obtain an epoxy group-containing compound in high yield. In addition, the peracids used as oxidizing agents are expensive and dangerous to handle, so they have the disadvantage of increasing industrial costs. Furthermore, as a method for producing an epoxy group-containing compound without using an organic peroxide, a halohydrin is produced by using hypohalous acid in an unsaturated compound, and then this halohydrin is treated with an alkali to produce an epoxy group. However, this method cannot be applied to olefins with complex structures. Therefore, an object of the present invention is to enable the reaction to be carried out under milder reaction conditions than those conventionally used for producing this type of epoxy group-containing compound, and to use an expensive oxidizing agent such as peracids. It is an object of the present invention to provide a new method that can be carried out industrially at low cost because it does not contain any oxidation, and can obtain an epoxy group-containing compound with good catalytic efficiency. [Means for Solving the Problems] In order to solve the above problems, the present invention provides general formula (I): [0009] [wherein R1 is hydrogen] an atom, a linear or branched alkyl group, or an aryl group, which may have a substituent, R2 and R3 may be the same or different, and a hydrogen atom, a substituted or unsubstituted alkyl group, or an aryl group. and may be bonded to each other to form a ring, R1 and R3 may be bonded to each other to form a ring, and R1, R2 and R3 may be bonded to each other to form a fused A double bond-containing compound represented by the general formula (II
), (II)′, (II)″, (III), (III)
′, (IV) or (IV)′: [Formula, (II)′, (II)″, (III
), (III)′, (IV) and
(IV)', R4, R6, R
7, R9, R10 and R12 may be the same or different and are a lower alkyl group, an aryl group, an alkoxy group or a halogenated alkyl group, or the following formula (a): -COOR13
(a) (wherein R13 is an alkyl group or an aryl group), which may have a substituent, R5, R8 and R11 may be the same or different, and a hydrogen atom, It is a halogen atom, a lower alkyl group, an aryl group, or an arylalkyl group, and may have a substituent, and R4 and R5 and R8 and R9 may each be bonded to each other to form a ring. , X is a halogen atom or ClO4 ￣, BF4
￣, BPh4￣ or PF6￣] and the following general formula (V): R14CHO
(V) [where R14
is a straight-chain or branched alkyl group or an aryl group, which may have a substituent]. VI): [0012] A method for producing an epoxy group-containing compound represented by [R1, R2 and R3 are as defined in the above general formula (I)] is provided. . The method for producing the epoxy group-containing compound of the present invention will be explained in detail below. In the general formula (I) representing the double bond-containing compound which is the starting material of the present invention,
R1 is a hydrogen atom, a linear or branched alkyl group, or an aryl group, and may have a substituent. Examples of the linear or branched alkyl group for R1 include ethyl group, n-propyl group, n-butyl group, sec
-butyl group, tert-butyl group, n-pentyl group, n
-hexyl group, n-heptyl group, n-octyl group, n-
Examples include nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, and the like. As the aryl group, for example,
Examples include phenyl group, p-methoxyphenyl group, p-chlorophenyl group, p-fluorophenyl group, and naphthyl group. R2 and R3 may be the same or different and are a hydrogen atom, a substituted or unsubstituted alkyl group, or an aryl group. Examples of the substituted or unsubstituted alkyl group include a methyl group, ethyl group, n-propyl group, and phenylmethyl group. Examples of the aryl group include a phenyl group, a naphthyl group, and a phenyl group.
Examples include aryl groups having substituents such as -fluorophenyl group, p-chlorophenyl group, and p-methoxyphenyl group. Further, R2 and R3 may be bonded to each other to form a ring, for example, may be bonded to each other to form a ring such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, etc. . Further, R1 and R3 may be bonded to each other to form a ring, for example, may be bonded to each other to form a group such as a norbornyl group. Furthermore, R1, R2 and R3 are
They may be bonded together to form a condensed ring, for example,
A condensed ring represented by the following formula: ##STR11## may be formed. Representative examples of the double bond-containing compound represented by the general formula (I) include 2-methyl-2-decene,
cis-2-octene, trans-2-octene,
Alicyclic unsaturated hydrocarbons such as 2-methyl-1-decene and 1-decene; aromatic unsaturated hydrocarbons such as styrene, or those represented by the following formulas (I-A) to (IL) can be mentioned. ##STR12## In the method of the present invention, in order to obtain an epoxy group-containing compound having a desired structure, the compound represented by the general formula (I) is A compound containing a heavy bond may be selected. In particular, in the method of the present invention, among the double bond-containing compounds represented by the general formula (I), the formula (I-A)
, (I-B), (I-C), (ID) and (I-E
) is useful as a method for producing the corresponding epoxy group-containing compound using as a starting material. In the method of the present invention, the double bond-containing compound represented by the general formula (I) is converted into the double bond-containing compound represented by the general formula (II), (
II)', (II)'', (III), (III)', (
This is a method of reacting at least one manganese compound represented by IV) or (IV)' with an oxygen-containing gas in the presence of an aldehyde compound represented by the general formula (V). The general formulas (II), (II)', and (II)'' representing the manganese compounds used in the method of the present invention
, (III), (III)', (IV) and (IV)
', R4, R6, R7, R9, R10
and R12 may be the same or different and are a lower alkyl group, an aryl group, an alkoxy group, a halogenated alkyl group, or a group represented by the above formula (a). Examples of the lower alkyl group include a methyl group, ethyl group, propyl group, isopropyl group, and t-butyl group, and examples of the aryl group include a phenyl group. Examples of the alkoxy group include a methoxy group and an ethoxy group. Examples of the halogenated alkyl group include a trifluoromethyl group. Further, in the formula (a), R13 is an alkyl group or an aryl group, and examples of the alkyl group include a methyl group and an ethyl group, and examples of the aryl group include a phenyl group. Furthermore, R4, R6, R7, R9
, R10 and R12 may have a substituent, and R4 , R6 , R7 , R9 , R
Examples of 10 and R12 include a methoxyphenyl group. Further, R5, R8 and R11 may be the same or different and are a hydrogen atom, a halogen atom, a lower alkyl group, an aryl group or an arylalkyl group. Examples of the halogen atom include chlorine, bromine, and fluorine, and examples of the lower alkyl group include a methyl group and an ethyl group. As an aryl group,
For example, phenyl group etc. can be mentioned. Also, R5, R
8 or R11 may have a substituent, and examples of R5, R8 or R11 having this substituent include o-, m- or p-methoxyphenyl group, 3,4-
Alternatively, examples thereof include a 3,5-dimethoxyphenyl group and a 3,4,5-trimethoxyphenyl group. Furthermore, R4 and R5, and R8
and R9 may be bonded to each other to form a ring, for example, R4 and R5 or R8 and R9
may be bonded to each other to form a ring such as a 5-membered ring or a 6-membered ring. [0028] In formulas (III) and (III)', X is a halogen atom, ClO4 ￣, BF4 ￣,
BPh4￣ or PF6￣. Examples of the halogen atom include chlorine, bromine, and iodine. This general formula (II), (II)' or (
Representative examples of the manganese compound represented by II)'' include compounds represented by the following formulas (II-A) to (II-I). [Chemical 17] [Chemical 18] [Chemical 19] Furthermore, (III) or (III)',
As representative examples of manganese compounds represented by (IV) or (IV)', the following formulas (III-A) and (
Examples include compounds represented by IV-A). ##STR20## In the method of the present invention, the general formula (II
), (II)′, (II)″, (III), (III)
The manganese compounds represented by ', (IV) or (IV)' may be used alone or in combination of two or more. [0034] The manganese compound may be obtained by any method and is not particularly limited. Alternatively, commercially available products may be used. [0035] This manganese compound is, for example, a diketone compound corresponding to the desired manganese compound, and MnCl
3 or Mn(NO3)3 by a desalting method. The product obtained in this manner may be used as it is after removing the reaction solvent and the like and then drying. Furthermore, it may be used as a purified product extracted with an organic solvent, purified by sublimation under reduced pressure, or purified by a combination of these purification methods and used. In the method of the present invention, the general formula (II
), (II)′, (II)″, (III), (III)
The amount of the manganese compound represented by ', (IV) or (IV)' is usually determined by the amount of the manganese compound represented by the general formula (I) which is the starting material.
) 0.0 per mole of double bond-containing compound represented by
The proportion is from 0.05 to 10 mol %, and in particular, the proportion from 0.0096 to 4 mol % is common since the yield of the epoxy group-containing compound is high. In the method of the present invention, the general formula (I
Along with manganese compounds represented by I) to (IV)′,
An aldehyde compound represented by the above general formula (V) is used. In the general formula (V), R14 is a linear or branched alkyl group, a cycloalkyl group, or an aryl group. Typical examples of linear or branched alkyl groups include methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, sec-butyl group, tert-butyl group, iso-butyl group, Examples of the cycloalkyl group include n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, etc. Examples include cyclohexyl group, cyclopentyl group, cycloheptyl group, and cyclooctyl group. Examples of the aryl group include phenyl group and p-methoxyphenyl group. In addition, these linear or branched alkyl groups, cycloalkyl groups, or aryl groups may have a substituent, for example, a halogen atom such as chlorine or fluorine, or a substituent such as a methoxy group. You may do so. Representative examples of the aldehyde compound represented by the general formula (V) include acetaldehyde, propionaldehyde, butyraldehyde, valeraldehyde, hexylaldehyde, heptylaldehyde, octylaldehyde, nonylaldehyde, decylaldehyde, undecylaldehyde, and dodecyl. Examples include aldehyde, isobutyraldehyde, 2-methylbutyraldehyde, 2-ethylbutyraldehyde, 2-methylvaleraldehyde, isovaleraldehyde, pivalaldehyde, 2-phenylpropionaldehyde, 3-phenylpropanal, cyclohexanecarbaldehyde, etc. . In the present invention, the aldehyde compounds represented by the general formula (V) may be used singly or in combination of two or more. The amount of the aldehyde compound represented by the general formula (V) to be used is usually 1 mole of the double bond-containing compound represented by the general formula (I) as a starting material.
It is generally more than 1 mole, preferably 1 to 10 moles. Further, this reaction can also be carried out using a solvent, and in this case, usually 1 to 10 mol of the above aldehyde is used per 1 mol of the double bond-containing compound represented by the above formula (I). The compound can also be used diluted with a solvent. As the solvent used, a solvent inert to the reaction can be used, and specific examples of such solvents include benzene, toluene, o-, m- or p-xylene, mesitylene, etc. Aromatic hydrocarbon solvents; halogenated hydrocarbon solvents such as chloroform, dichloromethane, and dichloroethane; ester solvents such as ethyl acetate, propyl acetate, butyl acetate; acetonitrile, acetone, diethyl ketone, THF, etc. . These solvents can be used alone or in combination. In particular, dichloroethane is preferable since it provides a high yield of the epoxy group-containing compound. The oxygen-containing gas used in the method of the present invention may be oxygen gas (pure oxygen) or oxygen-containing nitrogen gas (
For example, air) or an oxygen-containing inert gas such as oxygen-containing argon gas may be used. The partial pressure of oxygen in the oxygen-containing gas is preferably about 0.1 to 10 atm, more preferably 0.2 to 10 atm.
It is about 2.0 atm. When the partial pressure of oxygen is within this range, the reaction rate is fast and the reaction yield is good. The reaction temperature is usually about 0 to 100°C, and preferably 20 to 50°C, since the yield of the epoxy group-containing compound is increased. The reaction pressure is not particularly limited, and normal pressure is sufficient. The reaction in the method of the present invention may be carried out continuously in a liquid phase or may be carried out batchwise. Since the reaction mixture obtained by the above reaction usually contains by-products, unreacted starting materials, catalysts, etc., the epoxy group-containing compound, which is the object of the present invention,
It can be obtained by separating and purifying this reaction mixture. The separation method used is not particularly limited, and may be any known separation method such as distillation, adsorption, extraction, recrystallization, etc. The general formula (VI
) Representative examples of the epoxy group-containing compound represented by the following formula include those represented by the following formula. The epoxy group-containing compound obtained by the method of the present invention is useful, for example, as a synthetic intermediate or a raw material for a polymer. [Examples] The present invention will be specifically explained below with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples. (Examples 1 to 3) In each example, 3.0 mmol of 2-methyl-2-decene, 6.0 mmol of isobutyraldehyde, and the amounts of 1,
0.15 mmol each of 2-dichloroethane and the manganese compound represented by the formula (II-A) or (IV-A) shown above were charged. Then, in the reaction vessel,
Filled with 1 atm of oxygen gas, the reaction time shown in Table 1,
The reaction was carried out at room temperature. After completion of the reaction, the resulting reaction mixture was analyzed by gas chromatography, and the starting material 2-
Conversion rate of methyl-2-decene and product epoxide (2,2-dimethyl-3-heptyloxirane)
The yield was determined. The results are shown in Table 1. (Examples 4 to 9) In each example, 3.0 mmol of 2-methyl-2-decene, 6.0 mmol of isobutyraldehyde, and 5 ml of 1,2-dichloroethane were added to the reaction vessel as shown in Table 2. , respectively the above formulas (II-B) to (II-E), (II-A) and (I
0.15 mmol of manganese compound represented by I-F)
I prepared it. Next, 1 atm of O2 was filled into the reaction vessel, and the reaction was carried out at room temperature for the time shown in Table 1. After completion of the reaction, the resulting reaction mixture was analyzed by gas chromatography, and the starting material 2-
Conversion rate of methyl-2-decene and product epoxide (2,2-dimethyl-3-heptyloxirane)
The yield was determined. The results are shown in Table 2. (Examples 10 to 14) In each example, 3.0 mmol of 2-methyl-2-decene was added to the reaction vessel.
, 6.0 mmol of isobutyraldehyde and 10 ml of 1,2-dichloroethane in the amount shown in Table 3, and the formulas (IV-B) and (IV-C), respectively, as shown in Table 3.
, (II-A) and (IV-D). Next, 1 atm of O2 was filled into the reaction vessel, and the reaction was carried out at room temperature for the time shown in Table 3. After completion of the reaction, the resulting reaction mixture was analyzed by gas chromatography, and the starting material 2-
Conversion rate of methyl-2-decene and product epoxide (2,2-dimethyl-3-heptyloxirane)
The yield was determined. The results are shown in Table 3. (Examples 15 to 23) In each example, 3.0 mm of trans-2-octene was added to the reaction vessel.
ol, isobutyraldehyde 6.0 mmol and 1
, 10 ml of 2-dichloroethane and as shown in Table 4,
The above formulas (IV-D), (II-F), (IV-
B), (II-D), (II-C), (II-E), (
0.15 mmol of manganese compounds represented by II-G), (IV-E) and (II-I) were charged. Next, 1 atm of O2 was filled into the reaction vessel, and the reaction was carried out at room temperature for 14 hours. After completion of the reaction, the resulting reaction mixture was analyzed by gas chromatography, and the starting material tr
The conversion rate of ans -2-octene and the yield of the product 2,3-epoxyoctane are determined, and the 2
,3-epoxyoctane cis-isomer and trans
- content ratio (c-/t-) was determined. The results are shown in Table 4. (Examples 24 to 32) In each example, cis was used instead of trans-2-octene.
The reaction was carried out in the same manner as in Example 15, except that -2-octene was used and the manganese compounds shown in Table 5 were used. After completion of the reaction, the obtained reaction mixture was analyzed by gas chromatography, and the starting material ci
The conversion rate of s-2-octene and the product 2,
Determine the yield of 3-epoxyoctane, and further calculate the yield of 2,3
-The content ratio (c/t) of cis-form and trns-form of epoxy octane was determined. The results are shown in Table 5. (Examples 33 to 37) In each example, 3.0 mmol of 1-decene, 18.0 mmol of isovaleraldehyde and 10 ml of 1,2-dichloroethane were added to the reaction vessel as shown in Table 6. Formulas (II-B), (II-C), (II-D), (II-
Manganese compound 0 represented by E) and (II-A)
．． 15 mmol was charged. Next, 1 atm of O2 was filled into the reaction vessel, and the reaction was carried out at room temperature for the time shown in Table 6. After completion of the reaction, the resulting reaction mixture was analyzed by gas chromatography, and the starting material 1-
The conversion rate of decene and the yield of the product 1,2-epoxydecane were determined. The results are shown in Table 6. (Examples 38 to 42) In each example, 3.0 mmol of 2-octene, 6.0 mmol of the aldehyde compound shown in Table 7, and 10 ml of 1,2-dichloroethane, and the above formula (II- 0.15 mmol of a manganese compound represented by D) was charged. Next, 1 atm of O2 was filled into the reaction vessel, and the reaction was carried out at room temperature for 14 hours. After completion of the reaction, the resulting reaction mixture was analyzed by gas chromatography, and the starting material 2-
The conversion rate of octene and the yield of the product 2,3-epoxyoctane are determined, and the content ratio of cis-form and trans-form of the obtained 2,3-epoxyoctane (c-/t-) I asked for The results are shown in Table 7. [Table 1] (Examples 43 and 44) In each example, the double bond-containing compounds shown in Table 8 were added to the reaction vessel as starting materials.
1 mmol, isobutyraldehyde 2 mmol and 1,2-dichloroethane 5 ml, and the formula (II-D
0.05 mmol of a manganese compound represented by ) was charged. Next, 1 atm of O2 was filled into the reaction vessel, and the reaction was carried out at room temperature for 14 hours. After completion of the reaction, the resulting reaction mixture was analyzed by gas chromatography to determine the conversion rate of the starting material, the double bond-containing compound, the identity of the product, the epoxy group-containing compound, and its yield. I asked for it. The results are shown in Table 8. [Table 2] (Examples 45 and 46) In each example, the double bond-containing compounds shown in Table 9 were added to the reaction vessel as starting materials.
1 mmol, 3 mmol of isobutyraldehyde, and 5 ml of 1,2 dichloroethane, and the formula (II-D)
0.05 mmol of a manganese compound represented by: Next, 1 atm of O2 was filled into the reaction vessel, and the reaction was carried out at room temperature for 14 hours. After completion of the reaction, the resulting reaction mixture was analyzed by gas chromatography to determine the conversion rate of the starting material, the double bond-containing compound, the identity of the product, the epoxy group-containing compound, and its yield. I asked for it. The results are shown in Table 9. (Examples 47 to 49) In each example, 1 mmol of the double bond-containing compound shown in Table 10, 6 mmol of isobutyraldehyde, and 5 ml of 1,2-dichloroethane were placed in a reaction vessel as starting materials. The formula (I
0.05 mmol of manganese compound represented by ID)
I prepared it. Next, 1 atm of O2 was filled into the reaction vessel, and the reaction was carried out at room temperature for 14 hours. After completion of the reaction, the resulting reaction mixture was analyzed by gas chromatography to determine the conversion rate of the starting material, the double bond-containing compound, the identity of the product, the epoxy group-containing compound, and its yield. I asked for it. The results are shown in Table 10. [Table 4] (Examples 50 to 56) In each example, the substituent R in the following formula (I-X): Compound which is a group shown in 11: Cholesteryl benzoate
Example 50 Cholesteryl acetate
Example 51 Cholesteryl n-caproate Example 52 Cholesteryl n-caprylate
Example 53 Cholesterol Ethyl Carbonate Example 54 Cholesterol Formate Example 55 Cholesterol
0.5m each using Example 56 as raw material
mol, 2.0 mmol of isobutyraldehyde, and a manganese compound (Mn(
dpm) 2 ) ([bis(dipivaloylmethanato]manganese(II) ) 0.0047 mmol (3.0 mg,
0.94 mol % based on the raw materials) was dissolved in 1,2-dichloroethane and 5.0 ml of a solution was added thereto, and the mixture was stirred and reacted at room temperature for 2 hours in a pure oxygen atmosphere of 1 atm. After the reaction was completed, the reaction mixture was diluted with ethyl acetate and diluted with 1
It was washed successively with a 0% aqueous sodium carbonate solution and a saturated saline solution. After the solvent was distilled off under reduced pressure, the residue was purified by silica gel thin layer chromatography (developing solution: hexane/ethyl acetate mixture) to obtain white crystals. This white crystal was analyzed by NMR or high performance liquid chromatography (
When analyzed by HPLC), as shown in Table 11, the reaction product was α expressed by the following formula (I-X-α)
-Epoxide and β-epoxide represented by the following formula (I-X-β), and β-epoxide is α-epoxide.
It was found that it can be obtained in higher yield than epoxide. The results are shown in Table 11. embedded image (Examples 57 to 60) In each example, cholesteryl benzoate represented by the following formula: 0.0. 5m
mol, 2.0 mmol of isobutyraldehyde, and 0.0047 mmol of the manganese compound shown in Table 12,
Solutions 5 each dissolved in 1,2-dichloroethane
．． 0 ml of the solution was charged, and the mixture was stirred and reacted at room temperature for 2 hours under a pure oxygen atmosphere of 1 atm. After the reaction was completed, the reaction mixture was diluted with ethyl acetate and washed successively with a 10% aqueous sodium carbonate solution and saturated brine. After the solvent was distilled off under reduced pressure, the residue was purified by silica gel thin layer chromatography (developing solution: hexane/ethyl acetate mixture) to obtain white crystals. When this white crystal was analyzed by NMR, as shown in Table 12, the reaction products were α-epoxide represented by the following formula (VI-CBA-α) and α-epoxide represented by the following formula (VI-CBA-β). It was found that the β-epoxides were obtained in higher yields than the α-epoxides. The results are shown in Table 12. Comparative Examples 1 and 2 Instead of the manganese compound, as shown in Table 12, m-chloroperbenzoic acid (Comparative Example 1) and magnesium perphthalate (Comparative Example 2) were used, respectively. )
The reaction was carried out in the same manner as in Example 50, except that
The obtained reaction product was analyzed by NMR to determine the ratio of α-epoxide and β-epoxide in the reaction product. As a result, it was found that α-epoxide was obtained in higher yield than β-epoxide. The results are shown in Table 12. Note: Mn(acac)3: Manganese compound tris(acetylacetonato)manganese(II) Mn represented by formula (IIA)
(dpm)3: Manganese compound tris(dipivaloylmethanato)manganese(II) M represented by formula (IID)
n(acac)2: Manganese compound bis(acetylacetonato)manganese(II) Mn(
dpm)2: Manganese compound bis(dipivaloylmethanato)manganese(II) mC represented by formula (IID)
PBA: m-chloroperbenzoic acid MMPP: Magnesium perphthalate [0100] [Effects of the Invention] According to the method of the present invention, an epoxy group-containing compound can be converted into an epoxy group-containing compound by a novel reaction using a manganese compound with a specific structure as a catalyst. Obtainable. This reaction is
Compared to the conventional reactions that have been applied to the production of this type of epoxy group-containing compounds, the reaction can be carried out under milder reaction conditions such as reaction temperature and reaction pressure, and moreover, The conversion rate and the yield of the resulting epoxy group-containing compound can be maintained at a high level, and only a small amount of the manganese compound can be used, which is industrially advantageous.

Claims (1)

[Claims] [Claim 1] General formula (I): [Formula, R1 is a hydrogen atom, a linear or branched alkyl group, or an aryl group, which may have a substituent, R2 and R3 may be the same or different,
a hydrogen atom, a substituted or unsubstituted alkyl group, or an aryl group, which may be bonded to each other to form a ring, and R1 and R3 may be bonded to each other to form a ring; Furthermore, R1 , R2 and R3 may be bonded together to form a condensed ring].
(II)'', (III), (III)', (IV) or (IV)': [Formula (II)', (II)'', (III) , (III)
', (IV) and (IV)', R4, R6, R
7, R9, R10 and R12 may be the same or different and are a lower alkyl group, an aryl group, an alkoxy group or a halogenated alkyl group, or the following formula (a): -
COOR13 (
a) (here, R13 is an alkyl group or an aryl group), which may have a substituent, R5, R8 and R11 may be the same or different, and a hydrogen atom, It is a halogen atom, a lower alkyl group, an aryl group, or an arylalkyl group, and may have a substituent, and R4 and R5 and R8 and R9 may each be bonded to each other to form a ring. , X is a halogen atom or ClO4 ￣, BF4
￣, BPh4￣ or PF6￣] and the following general formula (V): R14CHO
(V) Reacts with an oxygen-containing gas in the presence of an aldehyde compound represented by [Here, R14 is a linear or branched alkyl group or an aryl group, which may have a substituent] A method for producing an epoxy group-containing compound represented by the general formula (VI): [R1 , R2 and R3 are as defined in the above general formula (I)], the method comprising the step of: