JP3029312B2 - Method for producing epoxy group-containing compound and novel iron compound - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing an epoxy group-containing compound, and more particularly to a method for obtaining an epoxy group-containing compound by a novel reaction carried out in the presence of a specific iron compound and an aldehyde compound, and a method suitable for the method. New iron compounds.

[0002]

2. Description of the Related Art Conventionally, as a method for producing an epoxy group-containing compound, a compound having a double bond is prepared 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, a peroxide-generating substance, for example, a mixture of glacial acetic acid and an unsaturated compound is added with a strong acid catalyst, and heated to 60 to 70 ° C., and hydrogen peroxide is added to generate peracetic acid. Then, a method of producing an epoxy group-containing compound using this peracetic acid has been performed.

[0003]

However, since the reaction in the above-mentioned method is a hypersensitive reaction, it is difficult to selectively carry out the epoxidation reaction. Some of the epoxy group-containing compounds may be polymerized. In addition, since this reaction is performed under severe reaction conditions at a reaction temperature of 50 ° C. or higher, side reactions easily occur, and an epoxy group-containing compound cannot be obtained in high yield. Also, the peracids used as oxidizing agents are expensive and dangerous to handle,
There is a disadvantage that the cost is industrially high.

Further, as a method for producing an epoxy group-containing compound without using an organic peroxide, a halohydrin is formed by using hypohalous acid as an unsaturated compound, and then the halohydrin is treated with an alkali to form an epoxy group. However, this method is not applicable to olefins having a complicated structure.

Accordingly, an object of the present invention is to perform the reaction under mild reaction conditions as compared with the reaction conventionally used for producing this type of epoxy group-containing compound, and to use an expensive oxidizing agent such as peracids. Accordingly, it is an object of the present invention to provide a novel method which can be carried out at low cost industrially and can obtain an epoxy group-containing compound with good catalytic efficiency.

[0006]

According to the present invention, there is provided a compound represented by the following general formula (I):

[0007]

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[In the formula, R ¹ is a linear or branched alkyl group or aryl group, which may have a substituent, R ² and R ³ may be the same or different, and represent a hydrogen atom, A substituted or unsubstituted alkyl group or aryl group, which may be mutually bonded to form a ring, and R ¹ and R ³ may be mutually bonded to form a ring; R ¹ , R ² and R ³ may be bonded together to form a condensed ring] by the general formulas (II), (II) ′ and (II) ″ , (III),
(III) ´, (IV) or (IV) ´:

[0009]

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[Formulas (II) ′, (II) ″, (III), (II)
In I) ′, (IV) and (IV) ′, R ⁴ , R ⁶ , R ⁷ ,
R ⁹ , R ¹⁰ and R ¹² may be the same or different and include a lower alkyl group, an aryl group, an alkoxy group or a halogenated alkyl group, or the following formula (a): —COOR ¹³ (a) (where R ¹³ Is an alkyl group or an aryl group)
And may have a substituent;
^5, R ⁸ and R ¹¹ may be the same or different, a hydrogen atom, a halogen atom, a lower alkyl group, an aryl group or an arylalkyl group which may have a substituent, and the R ⁴ R ⁵ and R ⁸ and R ⁹ may be mutually bonded to form a ring, and X is a halogen atom or ClO ₄ ⁻ , BF ₄ ⁻ , BPh ₄ ⁻ or PF ₆ ⁻ ]. And at least one selected from iron compounds represented by the following general formula (V): R ¹⁴ CHO (V) wherein R ¹⁴ is a linear or branched alkyl group or an aryl group, A reaction with an oxygen-containing gas in the presence of an aldehyde compound represented by the general formula (VI):

[0011]

Embedded image [Wherein R ¹ , R ² and R ³ are as defined in the above formula (I)].

Further, the present invention provides an iron compound which can be used in the method for producing an epoxy group-containing compound, represented by the following formula (IIA):

Embedded image And a novel iron compound represented by the formula:

Hereinafter, the method for producing the epoxy group-containing compound and the novel iron compound of the present invention will be described in detail.

In the general formula (I) representing the double bond-containing compound as the starting material of the present invention, R ¹ is a linear or branched alkyl or aryl group, which may have a substituent. . Examples of the linear or branched alkyl group for R ¹ include an ethyl group, an n-propyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, and an n-alkyl group.
Examples include a pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, and an n-dodecyl group. Examples of the aryl group include a phenyl group, a p-methoxyphenyl group,
p-chlorophenyl group, p-fluorophenyl group, naphthyl group and the like.

R ² and R ³ 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, an ethyl group, an n-propyl group, and a phenylmethyl group. Examples of the aryl group include a phenyl group, a naphthyl group, and a p-methyl group.
An aryl group having a substituent such as a fluorophenyl group, a p-chlorophenyl group, and a p-methoxyphenyl group is exemplified. R ² and R ³ may be bonded to each other to form a ring. For example, R ² and R ³ may be bonded to each other to form a ring such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, or a cyclooctyl group. Is also good.

Further, R ¹ and R ³ may be bonded to each other to form a ring. For example, R ¹ and R ³ may be bonded to each other to form a group such as a norbornyl group.

Further, R ¹ , R ² and R ³ may be simultaneously bonded to form a condensed ring.

Embedded image May form a condensed ring represented by

Representative examples of the double bond-containing compound represented by the above general formula (I) include 2-methyl-2-decene, c
alicyclic unsaturated hydrocarbons such as is-2-octene, trans-2-octene, 2-methyl-1-decene and 1-decene; aromatic unsaturated hydrocarbons such as styrene, and the following formula (I- A) to (II).

[0019]

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In the method of the present invention, the double bond-containing compound represented by the above formula (I) may be selected so as to obtain an epoxy group-containing compound having a desired structure. In particular, the method of the present invention comprises the above-mentioned compound (I-) among the double bond-containing compounds represented by formula (I).
B), (IC), (ID), (IH) and (I
It is useful as a method for producing a corresponding epoxy group-containing compound by using a compound represented by -I) 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 compound represented by the general formula (II) or (I
(I) ′, (II) ″, (III), (III) ′, (IV) or (I
V) 'is a method of reacting at least one selected from iron compounds represented by the formula (IV) with an oxygen-containing gas in the presence of the aldehyde compound represented by the general formula (IV).

The above general formulas (II), (II) ′, (II) ″, (III) and (I) representing the iron compound used in the method of the present invention.
II) ', (IV) and (IV)' wherein R ⁴ , R ⁶ ,
R ⁷ , R ⁹ , R ¹⁰ and R ¹² may be the same or different and are a lower alkyl group, an aryl group, an alkoxy group or a halogenated alkyl group, or a group represented by the above formula (a). As the lower alkyl group, for example,
Methyl group, ethyl group, propyl group, isopropyl group, t
-Butyl group and the like, and the aryl group include a phenyl group and the like. Examples of the alkoxy group include a methoxy group and an ethoxy group. Examples of the halogenated alkyl group include a trifluoromethyl group. In the above formula (a), R ¹³
Is an alkyl group or an aryl group.Examples of the alkyl group include a methyl group and an ethyl group.
Examples of the aryl group include a phenyl group.

Further, R ⁴ , R ⁶ , R ⁷ , R ⁹ , R ¹⁰ and R ¹² may have a substituent, and R ⁴ , R ⁶ , R ⁷ , R ⁹ , Examples of R ¹⁰ and R ¹² include a methoxyphenyl group and the like.

R ⁵ , R ⁸ and R ¹¹ 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, for example, chlorine, bromine and fluorine, and examples of the lower alkyl group include a methyl group,
And an ethyl group. Examples of the aryl group include a phenyl group. R ⁸ , R ⁸ or R ¹¹ may have a substituent. As R ⁸ , R ⁸ or R ¹¹ having the substituent, for example, an o-, m- or p-methoxyphenyl group; 3,4- or 3,5-
Examples thereof include a dimethoxyphenyl group and a 3,4,5-trimethoxyphenyl group.

Further, R ⁴ and R ⁵ , and R ⁸ and R ^5
9 may be mutually bonded to form a ring,
For example, R ⁴ and R ⁵ or R ⁸ and R ⁹ may be mutually bonded to form a ring such as a 5-membered ring or a 6-membered ring.

In the formulas (III) and (III) ′, X is a halogen atom or ClO ₄ ⁻ , BF ₄ ⁻ , BPh ₄ ⁻ or PF ₆ ⁻ . As the halogen atom, for example, chlorine,
Bromine, iodine and the like can be mentioned.

The general formula (II), (II) ′ or (I
Representative examples of the nickel compound represented by the formula (I) "include compounds represented by the following formulas (IIA) to (IIK).

[0028]

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Further, as typical examples of the iron compound represented by (III) or (III) 'and (IV) or (IV)', compounds represented by the following formulas (IIIA) and (IVA) can be mentioned. .

[0030]

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In the method of the present invention, the compound represented by the general formula (I)
I), (II) ′, (II) ″, (III), (III) ′, (IV)
Alternatively, the iron compound represented by (IV) ′ may be used alone or in combination of two or more.

The iron compound may be obtained by any method and is not particularly limited. Also,
A commercially available product may be used.

The iron compound may be, for example, a diketone compound corresponding to a desired iron compound, Fe (NO ₃ ) ₃ , Fe (NO ₃ ) ₂ ,
It can be produced by a desalting method using Cl ₃ or FeCl ₂ . The product thus obtained may be dried and used as it is after removing the reaction solvent and the like. Further, it may be used as a purified product extracted with an organic solvent,
Sublimation purification under reduced pressure may be used, or a combination of these purification methods may be used after purification.

Particularly, the iron compound represented by the formula (II-A) has not been described in the literature.
For example, 1,3-bis (p-methoxyphenyl) -1,3
Propanedione and FeCl ₃ in water / THF, water / MeO
H, water / Et ₂ O in each two-layer homogeneous solvent system at 0 ° C. to 10
The reaction can be carried out at 0 ° C. for 5 minutes to 3 hours.

In the method of the present invention, the compound represented by the general formula (I)
I), (II) ′, (II) ″, (III), (III) ′, (IV)
Alternatively, the amount of the iron compound represented by (IV) ′ is usually 0.005 to 10 mol% relative to 1 mol of the double bond-containing compound represented by the general formula (I) as a starting material. In particular, a ratio of 0.0096 to 4 mol% is generally used in that the yield of the epoxy group-containing compound is high.

In the method of the present invention, the above-mentioned general formula (I
The aldehyde compound represented by the general formula (V) is used together with the iron compounds represented by I) to (IV) ′.
In the general formula (V), R ¹⁴ is a linear or branched alkyl group, or a cycloalkyl group or an aryl group. Representative examples of the linear or branched alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert group.
-Butyl group, iso-butyl group, n-pentyl group, n-
Hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, and the like.Examples of the cycloalkyl group include a cyclohexyl group, a cyclopentyl group, and a cycloalkyl group. Examples include a heptyl group and a cyclooctyl group. As the aryl group,
For example, a phenyl group, a p-methoxyphenyl group and the like can be mentioned. Further, these linear or branched alkyl groups, or 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. It may be.

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. Aldehyde, isobutyraldehyde, 2-methylbutyraldehyde, 2-ethylbutyraldehyde, 2-methylvaleraldehyde, isovaleraldehyde, pivalaldehyde, 2-phenylpropionaldehyde, 3-phenylpropanal, cyclohexane carbaldehyde and the like can be mentioned. .

In the present invention, the aldehyde compound represented by the general formula (V) may be used alone or in combination of two or more.

The amount of the aldehyde compound represented by the general formula (V) is usually 1 to 1 mol of the double bond-containing compound represented by the general formula (I) as a starting material.
More than 1 mole, preferably 1 to 10 moles is common. This reaction can also be carried out using a solvent. In this case, usually, 1 to 10 mol of the aldehyde compound is added to 1 mol of the compound represented by the formula (I) in a solvent. Can also be used after dilution. As the solvent to be used, a solvent inert to the reaction can be used. Specific examples of such a solvent include benzene,
Aromatic hydrocarbon solvents such as toluene, o-, m- or p-xylene, mesitylene; halogenated hydrocarbon solvents such as chloroform, dichloromethane, dichloroethane; ester solvents such as ethyl acetate, propyl acetate and butyl acetate Acetonitrile, acetone, diethyl ketone, THF and the like. These solvents can be used alone or in combination. In particular, dichloroethane is preferable in that the yield of the epoxy group-containing compound is high.

The oxygen-containing gas used in the method of the present invention may be oxygen gas (pure oxygen) or oxygen-containing inert gas such as oxygen-containing nitrogen gas (for example, air) and oxygen-containing argon gas. The partial pressure of oxygen in the oxygen-containing gas is preferably about 0.1 atm to 10 kg / cm ² , more preferably about 0.2 to 1.0 atm. When the partial pressure of oxygen is within this range, the reaction rate is high 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 is separated from the reaction mixture. , And can be obtained by purification. The separation method used is not particularly limited, and may be, for example, a known separation method such as a method by distillation and adsorption, extraction, and recrystallization.

The above general formula (VI) obtained by the method of the present invention
Representative examples of the epoxy group-containing compound represented by the following formula include those represented by the following formula.

[0046]

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The epoxy group-containing compound obtained by the method of the present invention is useful for applications such as synthetic intermediates and polymer raw materials.

[0048]

EXAMPLES The present invention will now be described specifically with reference to examples and comparative examples, but the present invention is not limited to these examples.

Example 1 Tris [1,3-di (p-meth
Toxiphenyl) -1,3-propanedionato]
1,3-di (p-methoxy) was added to a 300 l round bottom flask.
(Cyphenyl) -1,3-propanedione 30.00 mmol
To 100 ml of methanol / THF mixed solvent (1/1)
A solution obtained by dissolution is charged, and iron trichloride is added under strong stirring.
An aqueous solution prepared by dissolving 0 mmol in 50 ml of water is added all at once.
Then, the mixture was stirred for 30 minutes to be reacted. Then the red that settled
The purple solid was filtered off and washed with water. The resulting solid
Dry at 110 ° C, 0.1mmHg for 6 hours to form red-purple solid
The reaction product of was obtained. When the obtained reaction product was analyzed,
At this time, the following results were obtained, and tris [1,3-di (p-
Methoxyphenyl) -1,3-propanedionato] with iron
It was confirmed that there was. (Yield: 52%) Properties: magenta powder Melting point: 278-279 ° C. Infrared absorption spectrum (KBr tablet method): The infrared absorption spectrum chart shown in FIG.
Wave number of important peak (cm ^-1) Is as shown below
Was. 2930, 2836, 1604, 1587, 152
7, 1492, 1460, 1377, 1305, 125
7, 1228, 1175 Elemental analysis: measured value (%): C,
66.78; H, 5.18 calculated (%): C, 6
4.83; H, 5.44

Examples 2 to 14 In each example, 3.0 mmol of 2-methyl-2-decene, 6.0 mmol of isobutyraldehyde and 1,2-dichloroethane 1 were placed in a reaction vessel.
0 ml, and as shown in Table 1, the formula (II
0.03 mmol of an iron compound represented by any of A) to (IIK), (IIIA) or (IVA) was charged. Next, 1 atm of oxygen gas was charged into the reaction vessel and reacted at room temperature for 4 hours.

After completion of the reaction, the obtained reaction mixture was analyzed by gas chromatography, and the starting material 2-
Conversion of methyl-2-decene and product epoxide (2,2-dimethyl-3-heptyloxirane)
Was determined. Table 1 shows the results.

[0052]

Examples 15 to 23 In each case, 3.0 mmol of styrene, 18.0 mmol of 2-ethylbutyraldehyde and 10 ml of 1,2-dichloroethane were placed in a reaction vessel.
And, as shown in Table 1, the above formulas (IIA) to
(IID), (IIF), (IIH), (IIJ), (IIIA)
And 0.03 mmol of the iron compound represented by (IVA). Next, 1 atm of O ₂ is charged into the reaction vessel,
The reaction was carried out at room temperature for the time shown in Table 1. After completion of the reaction, the obtained reaction mixture was analyzed by gas chromatography, and the conversion of styrene as a starting material and the yield of styrene oxide and benzaldehyde as products were determined. Table 2 shows the results.

[0054]

Examples 24 to 28 In each of the examples, 0.03 mmol of the iron compound represented by the formula (IIA) was used as the iron compound in the reaction vessel, and the amount of isobutyraldehyde used was as shown in Table 3. The reaction was carried out in the same manner as in Example 2 except that the reaction time was changed to 14 hours. After completion of the reaction, the obtained reaction mixture was analyzed by gas chromatography, and the conversion of 2-methyl-2-decene as a starting material and the epoxide (2,2
-Dimethyl-3-heptyloxirane). Table 3 shows the results.

[0056]

Examples 29 to 36 In each of the examples, 9.0 mmol of the aldehyde compound shown in Table 4 was used in place of isobutyraldehyde, and the compound represented by the above formula (IIA) was used as an iron compound. The reaction was carried out in the same manner as in Example 2 except that the time was changed. After completion of the reaction, the obtained reaction mixture was analyzed by gas chromatography, and the conversion of 2-methyl-2-decene as a starting material was determined.
And the product epoxide (2,2-dimethyl-3)
-Heptyloxirane). Table 4 shows the results.

[0058]

(Embodiments 37 to 42)
Instead of ethyl butyraldehyde, 18 mmol of the aldehyde compound shown in Table 5 was used.
The reaction was carried out in the same manner as in Example 15 except that 0.03 mmol of the compound represented by F) was used and the reaction time was 13 hours. After completion of the reaction, the obtained reaction mixture was analyzed by gas chromatography, and the conversion of styrene as a starting material and the yield of styrene oxide and benzaldehyde as products were determined. Table 5 shows the results.

[0060] *) GC peaks overlap due to the same retention time and cannot be quantified (Examples 43-49). In each case, 3.0 mmol of 1-decene and 18.0 mmol and 1 of the aldehyde compound shown in Table 6 were added to the reaction vessel. , 2-dichloroethane, 10 ml, and 0.03 mmol of the iron compound represented by the formula (IIA). Next, the reaction vessel was filled with 1 atm of oxygen gas and reacted at room temperature for 14 hours. After completion of the reaction, the obtained reaction mixture was analyzed by gas chromatography, and the conversion of 1-decene as a starting material and the yield of 1,2-epoxydecane as a product were determined. Table 6 shows the results.

[0061] * 1) GC peaks overlap due to the same phosphorus retention time and cannot be quantified. * 2) GC retention overlaps and cannot be quantified (Examples 50 to 68). In each case, compound 3 shown in Table 7 as a double bond-containing compound 6.0 mmol, isobutyraldehyde 6.0 mmol, 1,2-dichloroethane 10
ml, and 0.03 mmol of the compound represented by the formula (IIA) as an iron compound. Next, the reaction vessel was filled with 1 atm of oxygen gas and reacted at room temperature for 14 hours. After completion of the reaction, the obtained reaction mixture was analyzed by gas chromatography, and the identification of the product, an epoxy group-containing compound, and the yield thereof were obtained. Table 7 shows the results.

[0062]

[Table 1]

[Table 2]

[Table 3]

[Table 4]

[Table 5]

(Examples 69 to 73) In each of the examples, the olefins shown in Table 8 as 3.0 mm
ol, 2-ethylbutyraldehyde 18.0 mmol, 1,2
10 ml of dichloroethane and 0.03 mmol of the compound represented by the formula (IIF) as an iron compound were charged. Next, the reaction vessel was filled with 1 atm of oxygen gas and reacted at room temperature for 14 hours. After completion of the reaction, the obtained reaction mixture was analyzed by gas chromatography,
The product, the epoxy group-containing compound, was identified and its yield was determined. Table 8 shows the results.

[0064]

[Table 6]

According to the method of the present invention, an epoxy group-containing compound can be obtained by a novel reaction using an iron compound having a specific structure as a catalyst. This reaction can be carried out under mild reaction conditions such as a reaction temperature and a reaction pressure as compared with a reaction conventionally applied to the production of this type of epoxy group-containing compound, and the starting material double The conversion of the bond-containing compound and the yield of the resulting epoxy group-containing compound can be performed at a high level, and a small amount of iron compound can be used, which is industrially advantageous.

[Brief description of the drawings]

FIG. 1 is an infrared spectrum chart of a reaction product in Example 1.

──────────────────────────────────────────────────続 き Continued on the front page (72) Eiichiro Hata Inventor: Mitsui Petrochemical Industry Co., Ltd. JP-A-5-4980 (JP, A) JP-A-4-342598 (JP, A) JP-A-4-273867 (JP, A) JP-A-4-268878 (JP, A) 77479 (JP, A) JP-A-4-95079 (JP, A) JP-A-4-221391 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) C07D 301/04 C07F 15 / 02 CA (STN) REGISTRY (STN)

Claims (2)

(57) [Claims] 1. A compound of the general formula (I):[Wherein, R¹ Is a linear or branched alkyl group, aryl
And may have a substituent;^Two And R
^Three May be the same or different, and have a hydrogen atom or substitution
Or an unsubstituted alkyl or aryl group,
To form a ring;¹ And R^Three 
May be bonded to each other to form a ring;
¹ , R^Two And R^Three Are simultaneously bonded to form a fused ring
A double bond-containing compound represented by the general formula
Formulas (II), (II) ′, (II) ″, (III), (III) ′,
(IV) or (IV) ′:Embedded imageEmbedded image[Formula, (II) ′, (II) ″, (III), (III) ′, (IV)
And (IV) ′, R^Four , R⁶ , R⁷ , R⁹ , R^TenAnd
And R¹²May be the same or different, and a lower alkyl group,
Reel group, alkoxy group or halogenated alkyl group,
Alternatively, the following formula (a): -COOR¹³ (A) (where R¹³Is an alkyl group or an aryl group)
And may have a substituent;
^Five , R⁸ And R¹¹May be the same or different and represent hydrogen
Atom, halogen atom, lower alkyl group, aryl group or
Is an arylalkyl group, which may have a substituent
Ku and R^Four And R ^Five , And R⁸ And R⁹ Are mutual
And X may form a ring, and X is a halogen atom
Or ClO_Four ^-, BF_Four ^-, BPh_Four ^- Or PF₆ ^-so
At least one selected from iron compounds represented by
And the following general formula (V): R¹⁴CHO (V) [where R¹⁴Is a linear or branched alkyl group,
Or an aryl group, which may have a substituent].
Oxygen-containing gas in the presence of the aldehyde compound represented
General formula (VI) including a step of reacting with[R¹ , R^Two And R^Three Is defined in the general formula (I).
Epoxy group-containing compound represented by
Manufacturing method. 2. A compound represented by the following formula (IIA): A new iron compound represented by