阅读说明：本技术 环状氨基有机氧硅烷化合物及其制备方法 (Cyclic aminoorganooxysilane compounds and process for producing the same ) 是由 殿村洋一 于 2019-06-20 设计创作，主要内容包括：环状氨基有机氧硅烷化合物,具有以下通式(1)：<Image he="183" wi="700" file="DDA0002100979500000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>其中R<Sup>1</Sup>表示具有1-20个碳原子的取代或未取代的一价烃基,R<Sup>2</Sup>至R<Sup>5</Sup>各自独立地表示具有1-20个碳原子的取代或未取代的一价烃基,R<Sup>6</Sup>至R<Sup>8</Sup>各自独立地表示氢原子或具有1-20个碳原子的取代或未取代的一价烃基,R<Sup>9</Sup>和R<Sup>10</Sup>各自独立地表示任选地含有杂原子的具有1-20个碳原子的取代或未取代的二价烃基,m是0、1或2,并且n是0或1。(A cyclic aminoorganooxysilane compound having the following general formula (1): wherein R is 1 Represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, R 2 To R 5 Each independently represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, R 6 To R 8 Each independently represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, R 9 And R 10 Each independently represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 20 carbon atoms optionally containing heteroatoms, m is 0, 1 or 2, and n is 0 or 1.)

1. A cyclic aminoorganooxysilane compound having the following general formula (1):

wherein R is¹Represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, R²To R⁵Each independently represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, R⁶To R⁸Each independently represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, R⁹And R¹⁰Each independently represents a substituted or unsubstituted divalent hydrocarbon radical having 1 to 20 carbon atoms, optionally containing heteroatoms, m is 0, 1 or 2, and n is 0 or 1.

2. A process for producing the cyclic aminoorganoxysilane compound according to claim 1, which comprises distilling a reaction mixture obtained by reacting an aminoorganoxysilane compound having the following general formula (2) with an epoxy compound having the following general formula (3),

wherein R is²To R⁵、R⁹、R¹⁰M and n represent the same meanings as those defined above,

wherein R is¹And R⁶To R⁸Are meant to be the same as those defined above.

3. The process for preparing a cyclic aminoorganooxysilane compound of claim 2, further comprising distilling the reaction mixture in the presence of a basic catalyst or an acidic catalyst.

Technical Field

The present invention relates to a cyclic aminoorganoxysilane (aminoorganoxysilane) compound and a method for preparing the same, and more particularly to a cyclic aminoorganoxysilane compound useful as a silane coupling agent, a surface treatment agent, a resin additive, a coating additive, an adhesive, etc., and a method for preparing the same.

Background

The silane compound having an amino group is useful as a silane coupling agent, a surface treatment agent, a resin additive, a coating additive, an adhesive, etc. As such silane compounds having an amino group, organooxysilane compounds having a primary amino group such as aminopropyltrimethoxysilane, organooxysilane compounds having a secondary amino group such as N-phenylaminopropyltrimethoxysilane, organooxysilane compounds having a tertiary amino group such as dimethylaminopropyltrimethoxysilane, and the like are known.

However, since these silane compounds have only one amino group and one organoxysilyl (organosilyl) group per molecule, when they are used as silane coupling agents, surface treatment agents, resin additives, coating additives, adhesives, and the like, there may be cases where the effect due to the introduction of functional groups is less exerted.

In order to solve the above problems, tertiary aminosilane compounds having intramolecular organooxysilyl groups (see patent documents 1 and 3), secondary aminosilane compounds having intramolecular organooxysilyl groups (see patent document 2), and the like have been proposed.

When these compounds react with moisture in the air, hydroxyl groups are formed in addition to the originally possessed amino groups, and the above-described effects caused by the introduction of functional groups are enhanced. In addition, when the intramolecular organyloxy moiety reacts with moisture in the air, alcohols having low boiling points such as methanol and ethanol are not generated from the intramolecular organyloxy moiety, and thus the compound having the intramolecular organyloxy group can be used as a compound having a smaller environmental load.

Further, bis (trimethoxysilylpropyl) amine having two organoxysilyl groups and one secondary amino group has been proposed as a compound having a plurality of organoxysilyl groups, and it is known that a crosslinked network can be formed by its addition.

Reference list

Patent document 1: JP-A2010-120925

Patent document 2: JP-A2010-285406

Patent document 3: JP-A2014-001152

Disclosure of Invention

However, each of the compounds disclosed in patent documents 1 to 3 has only one amino group, one hydroxyl group formed by reaction with moisture in the air, and one organooxysilyl group per molecule as a functional group. Further, although bis (trimethoxysilylpropyl) amine has two organoxysilyl groups and one amino group as functional groups, in recent years, with the diversification of purposes as a silane coupling agent, a surface treatment agent, a resin additive, a coating additive, an adhesive, and the like, a silane compound having a higher addition effect is required. The addition effect may be low in the case when the compounds disclosed in patent documents 1 to 3 and bis (trimethoxysilylpropyl) amine are used, and a sufficient addition effect is not necessarily obtained.

The present invention has been made in view of the above circumstances, and an object of the present invention is to provide a silane compound having a large addition effect and generating less alcohol having a low boiling point when used as a silane coupling agent, a surface treatment agent, a resin additive, a coating additive, an adhesive, or the like, and a method for producing the silane compound.

As a result of diligent research to achieve the above object, the present inventors have found that when a specific cyclic aminoorganoxysilane compound is used as a silane coupling agent, a surface treatment agent, a resin additive, a coating additive, an adhesive, or the like, the addition effect is high and an alcohol having a low boiling point is less generated when used, thereby completing the present invention.

Namely, the present invention provides:

1. a cyclic aminoorganooxysilane compound having the following general formula (1):

wherein R is¹Represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, R²To R⁵Each independently represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, R⁶To R⁸Each independently represents a hydrogen atom orA substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, R⁹And R¹⁰Each independently represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 20 carbon atoms optionally containing heteroatoms, m is 0, 1 or 2, and n is 0 or 1;

2. a process for producing the cyclic aminoorganoxysilane compound according to item 1, which comprises distilling a reaction mixture obtained by reacting an aminoorganoxysilane compound having the following general formula (2) with an epoxy compound having the following general formula (3):

wherein R is²To R⁵、R⁹、R¹⁰M and n represent the same meanings as those defined above

Wherein R is¹And R⁶To R⁸Denotes the same meanings as those defined above; and

3. the process for producing a cyclic aminoorganooxysilane compound according to item 2, which further comprises distilling the reaction mixture in the presence of a basic catalyst or an acidic catalyst.

Effects of the invention

The cyclic aminoorganoxysilane compound according to the present invention can be used as a silane coupling agent, a surface treatment agent, a resin additive, a coating additive, an adhesive, etc. because the cyclic aminoorganoxysilane compound according to the present invention exerts a higher addition effect than conventionally known compounds.

Drawings

FIG. 1 is a photograph of the compound obtained in example 1¹H-NMR spectrum;

FIG. 2 is an IR spectrum of the compound obtained in example 1;

FIG. 3 is a drawing showing the results of example 2Of the compounds obtained¹H-NMR spectrum; and

fig. 4 is an IR spectrum of the compound obtained in example 2.

Detailed Description

Hereinafter, the present invention is described in detail.

The cyclic aminoorganooxysilane compound according to the present invention has the following general formula (1).

In the formula (1), R¹Represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, R²To R⁵Each independently represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, R⁶To R⁸Each independently represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, R⁹And R¹⁰Each independently represents a substituted or unsubstituted divalent hydrocarbon radical having 1 to 20 carbon atoms optionally containing heteroatoms, m is 0, 1 or 2 and preferably 0, and n is 0 or 1 and preferably 0.

Herein, R is¹Examples of the monovalent hydrocarbon group of (a) having 1 to 20 carbon atoms, preferably having 1 to 10 carbon atoms and more preferably having 1 to 5 carbon atoms include linear, branched or cyclic alkyl groups, alkenyl groups, aryl groups, aralkyl groups and the like.

Specifically, R¹Examples of the monovalent hydrocarbon group of (a) include: linear alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-decyl, dodecyl, tetradecyl, hexadecyl, octadecyl and eicosyl groups; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-hexyl (thexyl) and 2-ethylhexyl groups; cycloalkyl groups such as cyclopentyl and cyclohexyl groups; alkenyl groups such as vinyl, allyl, butenyl, and pentenyl groups; aryl groups such as phenyl and tolyl groups; aralkyl groups such as benzyl groups and the like. In particular, from raw material availability and productsFrom the viewpoint of usefulness, alkyl groups having 1 to 3 carbon atoms such as a methyl group, an ethyl group, an n-propyl group and an isopropyl group; alkenyl groups having 2 to 5 carbon atoms such as allyl groups, butenyl groups and pentenyl groups are preferred.

R²To R⁸Examples of the monovalent hydrocarbon group of (A) having 1 to 20 carbon atoms, preferably having 1 to 10 carbon atoms and more preferably having 1 to 5 carbon atoms include the monovalent hydrocarbon groups described above with respect to R¹Those exemplified are the same groups. In this case, R is also particularly from the standpoint of raw material availability and product usefulness²To R⁵Preferred examples of (b) include alkyl groups having 1 to 3 carbon atoms such as methyl group, ethyl group, propyl group and isopropyl group, and alkenyl groups having 2 to 5 carbon atoms such as allyl group, butenyl group and pentenyl group, and R⁶To R⁸Preferred examples of (b) include hydrogen atoms.

Meanwhile, R may be substituted with other substituents¹To R⁵Some or all of the hydrogen atoms in the above-mentioned monovalent hydrocarbon groups, and specific examples of such substituents include alkoxy groups such as a methoxy group, an ethoxy group, and an (iso) propoxy group; halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; a cyano group; an amino group; an acyl group having 2 to 10 carbon atoms; a trimethylsilyl group; trialkylsilyl groups, dialkylmonochlorosilyl groups, monoalkyldichlorosilyl groups, trialkoxysilyl groups, dialkylmonoalkoxysilyl groups or monoalkyldialkoxysilyl groups, wherein each alkyl group or each alkoxy group has from 1 to 5 carbon atoms. Two or more of these substituents may be used in combination, and the substitution position and the number of the substituents are not particularly limited.

At R which may contain hetero atoms⁹And R¹⁰Examples of hetero atoms in the divalent hydrocarbon group having 1 to 20 carbon atoms, preferably having 1 to 10 carbon atoms and more preferably having 1 to 5 carbon atoms include O, S, NH and the like.

The divalent hydrocarbon group may be any of linear and branchedAnd cyclic groups, and specific examples thereof include alkylene groups such as methylene, ethylene, methylethylene (propylene), trimethylene, methyltrimethylene, tetramethylene, hexamethylene, octamethylene, decamethylene, and isobutylene groups; arylene groups such as phenylene and methylphenylene groups; aralkylene (arylene) groups such as ethylene phenylene and ethylene phenylene methylene groups; oxaalkylene groups such as 2-oxapropylene, 2-oxapentylene, and the like. In particular, R is from the standpoint of raw material availability and product usefulness⁹Preferably an alkylene group having 1 to 3 carbon atoms, such as methylene, ethylene and trimethylene groups, and R¹⁰Preferably alkylene groups having 1 to 3 carbon atoms such as methylene, ethylene and trimethylene groups; and a 2-oxapropylene group.

Meanwhile, some or all of the hydrogen atoms in the above-mentioned divalent hydrocarbon groups may be substituted with other substituents, and specific examples of such substituents include halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; a cyano group; an amino group; an acyl group having 2 to 10 carbon atoms; a trimethylsilyl group; trialkylsilyl groups, dialkylmonochlorosilyl groups, monoalkyldichlorosilyl groups, trialkoxysilyl groups, dialkylmonoalkoxysilyl groups or monoalkyldialkoxysilyl groups, wherein each alkyl group or each alkoxy group has from 1 to 5 carbon atoms. Two or more of these substituents may be used in combination, and the substitution position and the number of the substituents are not particularly limited.

Specific examples of the cyclic aminoorganooxysilane compound having the general formula (1) include:

2, 2-dimethoxy-6-methoxymethyl-4- (trimethoxysilylmethyl) -1-oxa-4-aza-2-silacyclohexane (silacyclohexane),

2-methoxy-2-methyl-6-methoxymethyl-4- (dimethoxymethylsilylmethyl) -1-oxa-4-aza-2-silacyclohexane,

2, 2-dimethyl-6-methoxymethyl-4- (methoxymethylmethylsilylmethyl) -1-oxa-4-aza-2-silacyclohexane,

2, 2-diethoxy-6-methoxymethyl-4- (triethoxysilylmethyl) -1-oxa-4-aza-2-silacyclohexane,

2-ethoxy-2-methyl-6-methoxymethyl-4- (diethoxymethylsilylmethyl) -1-oxa-4-aza-2-silacyclohexane,

2, 2-dimethyl-6-methoxymethyl-4- (ethoxydimethylsilylmethyl) -1-oxa-4-aza-2-silacyclohexane,

2, 2-dimethoxy-8-methoxymethyl-6- (3-trimethoxysilylpropyl) -1-oxa-6-aza-2-silacyclooctane (silacyclooctane),

2-methoxy-2-methyl-8-methoxymethyl-6- (3-dimethoxymethylsilylpropyl) -1-oxa-6-aza-2-silacyclooctane,

2, 2-dimethyl-8-methoxymethyl-6- (3-methoxydimethylsilylpropyl) -1-oxa-6-aza-2-silacyclooctane,

2, 2-diethoxy-8-methoxymethyl-6- (3-triethoxysilylpropyl) -1-oxa-6-aza-2-silacyclooctane,

2-ethoxy-2-methyl-8-methoxymethyl-6- (3-diethoxymethylsilylpropyl) -1-oxa-6-aza-2-silacyclooctane,

2, 2-dimethyl-8-methoxymethyl-6- (3-ethoxydimethylsilylpropyl) -1-oxa-6-aza-2-silacyclooctane,

2, 2-dimethoxy-6-allyloxymethyl-4- (trimethoxysilylmethyl) -1-oxa-4-aza-2-silacyclohexane,

2-methoxy-2-methyl-6-allyloxymethyl-4- (dimethoxymethylsilylmethyl) -1-oxa-4-aza-2-silacyclohexane,

2, 2-dimethyl-6-allyloxymethyl-4- (methoxydimethylsilylmethyl) -1-oxa-4-aza-2-silacyclohexane,

2, 2-diethoxy-6-allyloxymethyl-4- (triethoxysilylmethyl) -1-oxa-4-aza-2-silacyclohexane,

2-ethoxy-2-methyl-6-allyloxymethyl-4- (diethoxymethylsilylmethyl) -1-oxa-4-aza-2-silacyclohexane,

2, 2-dimethyl-6-allyloxymethyl-4- (ethoxydimethylsilylmethyl) -1-oxa-4-aza-2-silacyclohexane,

2, 2-dimethoxy-8-allyloxymethyl-6- (3-trimethoxysilylpropyl) -1-oxa-6-aza-2-silacyclooctane,

2-methoxy-2-methyl-8-allyloxymethyl-6- (3-dimethoxymethylsilylpropyl) -1-oxa-6-aza-2-silacyclooctane,

2, 2-dimethyl-8-allyloxymethyl-6- (3-methoxydimethylsilylpropyl) -1-oxa-6-aza-2-silacyclooctane,

2, 2-diethoxy-8-allyloxymethyl-6- (3-triethoxysilylpropyl) -1-oxa-6-aza-2-silacyclooctane,

2-ethoxy-2-methyl-8-allyloxymethyl-6- (3-diethoxymethylsilylpropyl) -1-oxa-6-aza-2-silacyclooctane,

2, 2-dimethyl-8-allyloxymethyl-6- (3-ethoxydimethylsilylpropyl) -1-oxa-6-aza-2-silacyclooctane,

2, 2-dimethoxy-6-butoxymethyl-4- (trimethoxysilylmethyl) -1-oxa-4-aza-2-silacyclohexane,

2-methoxy-2-methyl-6-butoxymethyl-4- (dimethoxymethylsilylmethyl) -1-oxa-4-aza-2-silacyclohexane,

2, 2-dimethyl-6-butoxymethyl-4- (methoxydimethylsilylmethyl) -1-oxa-4-aza-2-silacyclohexane,

2, 2-diethoxy-6-butoxymethyl-4- (triethoxysilylmethyl) -1-oxa-4-aza-2-silacyclohexane,

2-ethoxy-2-methyl-6-butoxymethyl-4- (diethoxymethylsilylmethyl) -1-oxa-4-aza-2-silacyclohexane,

2, 2-dimethyl-6-butoxymethyl-4- (ethoxydimethylsilylmethyl) -1-oxa-4-aza-2-silacyclohexane,

2, 2-dimethoxy-8-butoxymethyl-6- (3-trimethoxysilylpropyl) -1-oxa-6-aza-2-silacyclooctane,

2-methoxy-2-methyl-8-butoxymethyl-6- (3-dimethoxymethylsilylpropyl) -1-oxa-6-aza-2-silacyclooctane,

2, 2-dimethyl-8-butoxymethyl-6- (3-methoxydimethylsilylpropyl) -1-oxa-6-aza-2-silacyclooctane,

2, 2-diethoxy-8-butoxymethyl-6- (3-triethoxysilylpropyl) -1-oxa-6-aza-2-silacyclooctane,

2-ethoxy-2-methyl-8-butoxymethyl-6- (3-diethoxymethylsilylpropyl) -1-oxa-6-aza-2-silacyclooctane,

2, 2-dimethyl-8-butoxymethyl-6- (3-ethoxydimethylsilylpropyl) -1-oxa-6-aza-2-silacyclooctane,

2, 2-dimethoxy-6-phenoxymethyl-4- (trimethoxysilylmethyl) -1-oxa-4-aza-2-silacyclohexane,

2-methoxy-2-methyl-6-phenoxymethyl-4- (dimethoxymethylsilylmethyl) -1-oxa-4-aza-2-silacyclohexane,

2, 2-dimethyl-6-phenoxymethyl-4- (methoxydimethylsilylmethyl) -1-oxa-4-aza-2-silacyclohexane,

2, 2-diethoxy-6-phenoxymethyl-4- (triethoxysilylmethyl) -1-oxa-4-aza-2-silacyclohexane,

2-ethoxy-2-methyl-6-phenoxymethyl-4- (diethoxymethylsilylmethyl) -1-oxa-4-aza-2-silacyclohexane,

2, 2-dimethyl-6-phenoxymethyl-4- (ethoxydimethylsilylmethyl) -1-oxa-4-aza-2-silacyclohexane,

2, 2-dimethoxy-8-phenoxymethyl-6- (3-trimethoxysilylpropyl) -1-oxa-6-aza-2-silacyclooctane,

2-methoxy-2-methyl-8-phenoxymethyl-6- (3-dimethoxymethylsilylpropyl) -1-oxa-6-aza-2-silacyclooctane,

2, 2-dimethyl-8-phenoxymethyl-6- (3-methoxydimethylsilylpropyl) -1-oxa-6-aza-2-silacyclooctane,

2, 2-diethoxy-8-phenoxymethyl-6- (3-triethoxysilylpropyl) -1-oxa-6-aza-2-silacyclooctane,

2-ethoxy-2-methyl-8-phenoxymethyl-6- (3-diethoxymethylsilylpropyl) -1-oxa-6-aza-2-silacyclooctane,

2, 2-dimethyl-8-phenoxymethyl-6- (3-ethoxydimethylsilylpropyl) -1-oxa-6-aza-2-silacyclooctane and the like.

Examples of the method for producing the cyclic aminoorganooxysilane compound having general formula (1) according to the present invention include: a method comprising distilling a reaction mixture obtained by reacting an aminoorganooxysilane compound having the following general formula (2) (hereinafter, simply referred to as compound (2)) with an epoxy compound having the following general formula (3) (hereinafter, simply referred to as compound (3)):

wherein R is¹To R¹⁰M and n represent the same meanings as described above.

More specifically, it is considered that as shown in the following scheme, in the first step, the compound (2) is reacted with the compound (3) to form an aminoorganoxysilane compound having a hydroxyl group, and in the second step, i.e., in the step of distilling the reaction solution containing the aminoorganoxysilane compound having a hydroxyl group, intramolecular dealcoholization cyclization is caused to form the objective cyclic aminoorganoxysilane compound.

Specific examples of the compound (2) include bis (trimethoxysilylmethyl) amine, bis (dimethoxymethylsilylmethyl) amine, bis (methoxydimethylsilylmethyl) amine, bis (triethoxysilylmethyl) amine, bis (diethoxymethylsilylmethyl) amine, bis (ethoxydimethylsilylmethyl) amine, bis (3-trimethoxysilylpropyl) amine, bis (3-dimethoxymethylsilylpropyl) amine, bis (3-methoxydimethylsilylpropyl) amine, bis (3-triethoxysilylpropyl) amine, bis (3-diethoxymethylsilylpropyl) amine, bis (3-ethoxydimethylsilylpropyl) amine and the like.

Specific examples of the compound (3) include glycidyl methyl ether, allyl glycidyl ether, butyl glycidyl ether, glycidyl phenyl ether and the like.

The compounding ratio of the compound (2) and the compound (3) is not particularly limited, but from the viewpoint of reactivity and productivity, the compound (3) is preferably used in an amount of 0.2 to 5.0mol and more preferably 0.5 to 2.0mol per 1mol of the compound (2).

Although the first-step reaction proceeds even without a catalyst, a basic catalyst or an acidic catalyst may be used for the purpose of improving the reaction rate.

Specific examples of the basic catalyst include sodium hydroxide, potassium hydroxide, sodium methoxide, sodium ethoxide, a methanol solution of sodium methoxide, an ethanol solution of sodium ethoxide, and the like.

On the other hand, specific examples of the acidic catalyst include inorganic acids such as sulfuric acid, hydrochloric acid and nitric acid; sulfonic acid compounds such as methanesulfonic acid, benzenesulfonic acid, toluenesulfonic acid, dodecylbenzenesulfonic acid, trifluoromethanesulfonic acid and salts thereof and the like.

The amount of the catalyst to be used is not particularly limited, but from the viewpoint of reactivity and productivity, preferably from 0.0001 to 0.2mol and more preferably from 0.001 to 0.1mol of the catalyst is used per 1mol of the compound (2).

Meanwhile, although the reaction in the first step proceeds even without a solvent, a solvent may also be used. Examples of the solvent used include hydrocarbon-based solvents such as pentane, hexane, cyclohexane, heptane, isooctane, benzene, toluene and xylene; ether-based solvents such as diethyl ether, tetrahydrofuran and bisAn alkane; ester-based solvents such as ethyl acetate and butyl acetate; aprotic polar solvents such as acetonitrile, N-dimethylformamide and N-methylpyrrolidone; chlorinated hydrocarbon-based solvents such as dichloromethane and chloroform; alcohol-based solvents such as methanol, ethanol, 1-propanol, and 2-propanol, and the like. These solvents may be used alone or in combination of two or more types.

In the distillation method of the second step, although a general distillation method may be used, in order to accelerate the reaction rate of the dealcoholization reaction, or in order to split the intermolecular dealcoholization condensation polymer compound present in the reaction solution and to convert it into the target cyclic aminoorganooxysilane compound, it is preferable to conduct the distillation in the presence of a basic catalyst or an acidic catalyst.

As the basic catalyst and the acidic catalyst in this case, the same catalysts as described above can be used.

The amount of the catalyst to be used is not particularly limited, but from the viewpoint of reactivity and productivity, preferably from 0.0001 to 0.2mol and more preferably from 0.001 to 0.1mol of the catalyst is used per 1mol of the compound (3).

Meanwhile, in the second step, the reaction solution obtained in the first step may be distilled as it is or a solvent may be further added to the reaction solution for distillation.

Further, examples of the solvent in this case include hydrocarbon-based solvents such as pentane, hexane, cyclohexane, heptane, isooctane, decane, tridecane, octadecane, eicosane, benzene, toluene, xylene and dodecylbenzene; ether-based solvents such as diethyl ether, tetrahydrofuran, bisAlkyl and diphenyl ether; ester-based solvents such as ethyl acetate, butyl acetate, methyl stearate, and methyl oleate; aprotic polar solvents such as acetonitrile, N-dimethylformamide and N-methylpyrrolidone; chlorinated hydrocarbon-based solvents such as dichloromethane andchloroform; alcohol-based solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-decanol, 1-octadecanol, 2-hexyl-1-decanol, oleyl alcohol, 1-docosanol, and the like. These solvents may be used alone or in combination of two or more types.