Method for producing silane coupling agent

Abstract

To provide a novel method for producing a silane coupling agent.SOLUTION: A method for producing a silane coupling agent includes synthesizing a silane coupling agent, or a compound (I), by a vinyl group introduction step, a hydrosilylation step and a diazotizing step. In the compound (I), A is a C3-26 divalent aliphatic hydrocarbon group or aromatic hydrocarbon group optionally having a heteroatom and optionally having a substituent, and R1, R2 and R3 independently represent a substituent, where at least one of R1, R2 and R3 is an alkoxy group.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a method for producing a silane coupling agent.

Background Art

[0002] Conventionally, a silane coupling agent having functional groups that bind to both organic and inorganic materials in the molecule is known (for example, Patent Document 1).

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0004] An object of the present invention is to provide a method for producing a novel silane coupling agent.

Means for Solving the Problems

[0005] As a result of intensive studies on the above problems, the present inventors have found that the above problems can be solved by the following configuration.

[0006] (1) A vinyl group introduction step of synthesizing a compound (IV) described below by reacting a compound (III) described below with a compound represented by CH2=CH-R-OH (wherein R represents a divalent aliphatic hydrocarbon group or aromatic hydrocarbon group having 1 to 24 carbon atoms which may have a hetero atom and may have a substituent), and A hydrosilylation step of synthesizing a compound (VII) described below by reacting the above compound (IV) with a compound (VI) described below, A method for producing a silane coupling agent, comprising a diazotization step of synthesizing a silane coupling agent represented by the following compound (I) by reacting the following compound (II) with the above compound (VII). (2) A vinyl group introduction step of synthesizing the following compound (IV) by reacting the following compound (III) with a compound represented by CH2=CH-R-OH (wherein R represents a divalent aliphatic hydrocarbon group or aromatic hydrocarbon group having 1 to 24 carbon atoms, which may have a hetero atom and may have a substituent), a diazotization step of synthesizing the following compound (V) by reacting the following compound (II) with the above compound (IV), A method for producing a silane coupling agent, comprising a hydrosilylation step of synthesizing a silane coupling agent represented by the following compound (I) by reacting the above compound (V) with the following compound (VI).

Advantages of the Invention

[0007] As shown below, according to the present invention, a method for producing a novel silane coupling agent can be provided.

Brief Description of the Drawings

[0008]

Figure 1

Figure 2

Figure 3

Modes for Carrying Out the Invention

[0009] The method for producing a silane coupling agent of the present invention will be described below. In the present specification, a numerical range represented by "~" means a range including the numerical values described before and after "~" as the lower limit value and the upper limit value. Further, each component may be used alone or in combination of two or more. Here, when two or more of each component are used in combination, the content of that component refers to the total content unless otherwise specified.

[0010] The first aspect of the method for producing the silane coupling agent of the present invention (hereinafter, also referred to as "the method of the present invention") (hereinafter, also referred to as "the method 1 of the present invention") is a vinyl group introduction step of synthesizing a compound (IV) described below by reacting a compound (III) described below with a compound represented by CH2=CH-R-OH (wherein R represents a divalent aliphatic hydrocarbon group or aromatic hydrocarbon group having 1 to 24 carbon atoms which may have a hetero atom and may have a substituent) (hereinafter, also referred to as "specific alcohol"), a hydrosilylation step of synthesizing a compound (VII) described below by reacting the compound (IV) with a compound (VI) described below, and a diazotization step of synthesizing a silane coupling agent (hereinafter, also referred to as "specific silane coupling agent") which is a compound (I) described below by reacting a compound (II) described below with the compound (VII), which is a method for producing a silane coupling agent.

[0011] Further, the second aspect of the method of the present invention (hereinafter, also referred to as "the method 2 of the present invention") is a vinyl group introduction step of synthesizing a compound (IV) described below by reacting a compound (III) described below with a compound represented by CH2=CH-R-OH (wherein R represents a divalent aliphatic hydrocarbon group or aromatic hydrocarbon group having 1 to 24 carbon atoms which may have a hetero atom and may have a substituent) (specific alcohol), a diazotization step of synthesizing a compound (V) described below by reacting a compound (II) described below with the compound (IV), and a hydrosilylation step of synthesizing a silane coupling agent (specific silane coupling agent) which is a compound (I) described below by reacting the compound (V) with a compound (VI), which is a method for producing a silane coupling agent.

[0012] Since the method of the present invention has such a configuration, a specific silane coupling agent can be obtained in a high yield. In addition, in Method 2 of the present invention, as described later, when a Karstedt catalyst is used as a preferred embodiment, when the Karstedt catalyst is used, since the decomposition reaction of the diazo group is also promoted, a long reaction time may be difficult (the concerted reaction of reaction and decomposition). Since the target product may disappear when reacting for a long time, strict control of time and temperature may be required. On the other hand, in Method 1 of the present invention, since a catalyst that is easier to handle than the Karstedt catalyst can be applied, a specific silane coupling agent can be obtained in a higher yield.

[0013] Further, when the above specific silane coupling agent is blended into a mixture of an organic material (especially natural rubber) and an inorganic material (especially silica), the dispersibility of the inorganic material in the organic material becomes extremely high. This is presumably because when the specific silane coupling agent is blended into the above mixture, the alkoxysilyl group of the specific silane coupling agent binds to the inorganic material, and the diazo group (=N2) binds to the organic material, and the reactivity of the diazo group with respect to the organic material is extremely high. It is considered that the diazo group decomposes to pass through a carbene (a highly reactive species) and reacts with an organic material (for example, an olefin (especially a double bond in rubber)). In particular, an electron-deficient carbene and an electron-rich polysubstituted alkene are considered to be compatible and can acquire reactivity.

[0014] Hereinafter, Method 1 and Method 2 of the present invention will be described.

[0015] [Method 1 of the Present Invention] As described above, Method 1 of the present invention is a vinyl group introduction step of synthesizing a compound (IV) described later by reacting a compound (III) described later with a specific alcohol, and a hydrosilylation step of synthesizing a compound (VII) described later by reacting the compound (IV) with a compound (VI) described later, By reacting the compound (II) described below with the compound (VII) above, a diazotization step of synthesizing a silane coupling agent (specific silane coupling agent), which is the compound (I) described below, is provided. This is a method for producing a silane coupling agent.

[0016] Hereinafter, each step will be described.

[0017] 〔Vinyl group introduction step〕 The above vinyl group introduction step is a step of synthesizing the following compound (IV) by reacting the following compound (III) with a specific alcohol.

[0018] <Compound (III)>

[0019] Compound (III)

Chemical formula

[0020] In compound (III), X1 and X2 each independently represent a halogen atom.

[0021] As described above, in compound (III), X1 and X2 each independently represent a halogen atom. The halogen atom is not particularly limited, but it is preferably a bromine atom because the yield of the specific silane coupling agent is higher and the effect of improving the dispersibility of the inorganic material of the obtained specific silane coupling agent is more excellent. Hereinafter, "the yield of the specific silane coupling agent is higher and the effect of improving the dispersibility of the inorganic material of the obtained specific silane coupling agent is more excellent" is also referred to as "the effects of the present invention are more excellent".

[0022] <Specific alcohol> The above-mentioned specific alcohol is a compound represented by CH2=CH-R-OH (wherein R represents a divalent aliphatic hydrocarbon group or aromatic hydrocarbon group having 1 to 24 carbon atoms, which may have a hetero atom and may have a substituent). The above-mentioned aliphatic hydrocarbon group may be linear, branched or cyclic. For the reason that the effects of the present invention are more excellent, the above-mentioned R is preferably a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms (particularly an alkylene group).

[0023] <Compound (IV)>

[0024] Compound (IV)

Chemical formula

[0025] In Compound (IV), R represents a divalent aliphatic hydrocarbon group or aromatic hydrocarbon group having 1 to 24 carbon atoms, which may have a hetero atom and may have a substituent, and X represents a halogen atom.

[0026] Specific examples and preferred embodiments of the above-mentioned R are the same as those of R in the above-mentioned specific alcohol. Also, specific examples and preferred embodiments of the above-mentioned X are the same as those of X in the above-mentioned Compound (III).

[0027] <Preferred embodiment> For the reason that the effects of the present invention are more excellent, the above-mentioned vinyl group introduction step is preferably a step of synthesizing the above-mentioned Compound (IV) by reacting the above-mentioned Compound (III) with the above-mentioned specific alcohol in the presence of sodium hydrogen carbonate and acetonitrile.

[0028] 〔Hydrosilylation step〕 The above-mentioned hydrosilylation step is a step of synthesizing the following Compound (VII) by reacting the Compound (IV) obtained in the above-mentioned vinyl group introduction step with the following Compound (VI).

[0029] <Compound (VI)>

[0030] Compound (VI)

Chem.

[0031] In Compound (VI), R1, R2, and R3 each independently represent a substituent, provided that at least one of R1, R2, and R3 is an alkoxy group.

[0032] The number of carbon atoms of the above alkoxy group is not particularly limited, but is preferably 1 to 5 for better effects of the present invention.

[0033] Specific examples of the case where the above substituent is other than an alkoxy group include an aliphatic hydrocarbon group, an aromatic hydrocarbon group, or a group combining these. The above aliphatic hydrocarbon group may be linear, branched, or cyclic. Specific examples of the above aliphatic hydrocarbon group include a linear or branched alkyl group (especially having 1 to 30 carbon atoms), a linear or branched alkenyl group (especially having 2 to 30 carbon atoms), a linear or branched alkynyl group (especially having 2 to 30 carbon atoms), and the like. Examples of the above aromatic hydrocarbon group include aromatic hydrocarbon groups having 6 to 18 carbon atoms such as a phenyl group, a tolyl group, a xylyl group, and a naphthyl group. When the above substituent is other than an alkoxy group, it is preferably an aliphatic hydrocarbon group, and more preferably an alkyl group (especially having 1 to 5 carbon atoms) for better effects of the present invention.

[0034] <Compound (VII)>

[0035] Compound (VII)

Chem.

[0036] In compound (VII), A represents a divalent aliphatic hydrocarbon group or aromatic hydrocarbon group having 3 to 26 carbon atoms, which may have a heteroatom and may have a substituent. The definitions of R1, R2 and R3 are the same as those of R1, R2 and R3 in compound (VI) described above, and the definition of X is the same as that of X in compound (IV) described above.

[0037] As described above, in compound (VII), A represents a divalent aliphatic hydrocarbon group or aromatic hydrocarbon group having 3 to 26 carbon atoms, which may have a heteroatom and may have a substituent. For the reason that the effects of the present invention are more excellent, the above A is preferably a group represented by -CH2CH2-R. Here, the definition, specific and preferred embodiments of R are the same as those of R in the specific alcohol described above.

[0038] As described above, in compound (VII), the definitions of R1, R2 and R3 are the same as those of R1, R2 and R3 in compound (VI) described above. The specific examples and preferred embodiments of the above R1, R2 and R3 are also the same as those of R1, R2 and R3 in compound (VI) described above.

[0039] As described above, in compound (VII), the definition of X is the same as that of X in compound (IV) described above. The specific examples and preferred embodiments of the above X are also the same as those of X in compound (IV) described above.

[0040] <Preferred Embodiment> For the reason that the effects of the present invention are more excellent, the above hydrosilylation step It is preferable that the compound (VII) described above is synthesized by subjecting the compound (IV) obtained in the above vinyl group introduction step and the compound (VI) described above to a hydrosilylation reaction at room temperature in the presence of an iridium catalyst and dichloromethane.

[0041] Examples of the iridium catalyst include iridium salts and iridium complexes. Specific examples of the iridium salt include iridium trichloride, iridium tetrachloride, chloroiridic acid, sodium chloroiridate, potassium chloroiridate, and the like. Specific examples of the iridium complex include chloro(1,5-cyclooctadiene)iridium(I) dimer, bromo(1,5-cyclooctadiene)iridium(I) dimer, iodo(1,5-cyclooctadiene)iridium(I) dimer, chloro(2,5-norbornadiene)iridium(I) dimer, bromo(2,5-norbornadiene)iridium(I) dimer, iodo(2,5-norbornadiene)iridium(I) dimer, 1,5-cyclooctadiene(acetylacetonato)iridium(I), chlorobis(cyclooctene)iridium(I) dimer, chlorocarbonylbis(triphenylphosphine)iridium(I), and the like. In particular, due to the more excellent effects of the present invention and the like, it is preferable to use chloro(1,5-cyclooctadiene)iridium(I) dimer.

[0042] 〔Diazoation step〕 The above diazoation step is a step of synthesizing a silane coupling agent (specific silane coupling agent) represented by the following compound (I) by reacting the following compound (II) with the compound (VII) obtained in the above hydrosilylation step.

[0043] <Compound (II)>

[0044] Compound (II)

Chemical formula

[0045] In Compound (II), Ts represents a tosyl group.

[0046] The synthesis method of compound (II) is not particularly limited, but for the reason that the effects of the present invention are more excellent, a method of reacting p-toluenesulfonyl hydrazide with para-toluenesulfonyl chloride in the presence of pyridine and dichloromethane is preferred.

[0047] <Compound (I)>

[0048] Compound (I)

Chemical formula

[0049] In compound (I), the definition of A is the same as that of A in compound (VII) described above, and the definitions of R1, R2 and R3 are the same as those of R1, R2 and R3 in compound (VI) described above.

[0050] As described above, in compound (I), the definition of A is the same as that of A in compound (VII) described above. The specific examples and preferred embodiments of the above A are also the same as those of A in compound (VII) described above.

[0051] As described above, in compound (I), the definitions of R1, R2 and R3 are the same as those of R1, R2 and R3 in compound (VI) described above. The specific examples and preferred embodiments of the above R1, R2 and R3 are also the same as those of R1, R2 and R3 in compound (VI) described above.

[0052] <Preferred embodiment> For the reason that the effects of the present invention are more excellent, the above diazotization step It is preferred that the above-mentioned compound (II) and the compound ((VII) obtained in the above hydrosilylation step are subjected to a diazotization reaction in the presence of tetramethylguanidine and tetrahydrofuran to synthesize the silane coupling agent which is the above-mentioned compound (I).

[0053] [Method 2 of the present invention] As described above, Method 2 of the present invention By reacting the compound (III) described below with a compound represented by CH2=CH-R-OH (wherein R represents a divalent aliphatic hydrocarbon group or aromatic hydrocarbon group having 1 to 24 carbon atoms which may have a hetero atom and may have a substituent) (specific alcohol), a vinyl group introduction step of synthesizing the compound (IV) described below, A diazotization step of synthesizing the compound (V) described below by reacting the compound (II) described below with the compound (IV); and A hydrosilylation step of synthesizing a silane coupling agent (specific silane coupling agent) which is the compound (I) described below by reacting the compound (V) described above with the compound (VI) described below.

[0054] Hereinafter, each step will be described.

[0055] 〔Vinyl group introduction step〕 The above vinyl group introduction step is the same as the vinyl group introduction step of Method 1 of the present invention described above.

[0056] 〔Diazotization step〕 The above diazotization step is a step of synthesizing the following compound (V) by reacting the following compound (II) with the compound (IV) obtained in the above vinyl group introduction step.

[0057] <Compound (II)> The above compound (II) is the same as the compound (II) used in the diazotization step of Method 1 of the present invention described above.

[0058] <Compound (V)>

[0059] Compound (V)

Chemical formula

[0060] In the compound (V), R represents a divalent aliphatic hydrocarbon group or aromatic hydrocarbon group having 1 to 24 carbon atoms, which may have a hetero atom and may have a substituent.

[0061] Specific examples and preferred embodiments of the above R are the same as those of R in the above-mentioned specific alcohol.

[0062] <Preferred Embodiment> For the reason that the effects of the present invention are more excellent, the above diazotization step is preferably a step of synthesizing the above compound (V) by subjecting the above compound (II) and the compound (IV) obtained in the above vinyl group introduction step to a diazotization reaction in the presence of diazabicycloundecene and tetrahydrofuran.

[0063] 〔Hydrosilylation Step〕 The above hydrosilylation step is a step of synthesizing a silane coupling agent (specific silane coupling agent) which is the following compound (I) by reacting the compound (V) obtained in the above diazotization step with the following compound (VI).

[0064] <Compound (VI)> The above compound (VI) is the same as the compound (VI) used in the hydrosilylation step of Method 1 of the present invention described above.

[0065] <Compound (I)> The above compound (I) (specific silane coupling agent) is the same as the compound (I) (specific silane coupling agent) synthesized in the diazotization step of Method 1 of the present invention described above.

[0066] <Preferred Embodiment> For the reason that the effects of the present invention are more excellent, the above hydrosilylation step is preferably a step of synthesizing the above compound (I) (specific silane coupling agent) by subjecting the compound (V) obtained in the above diazotization step and the above compound (VI) to a hydrosilylation reaction in the presence of a Karstedt catalyst.

[0067] [Use] The above-mentioned specific silane coupling agent is particularly useful as a compounding agent for a mixture of organic materials (especially natural rubber) and inorganic materials (especially silica).

Examples

[0068] Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited thereto.

[0069] 〔Example 1〕

[0070] <Synthesis of Compound (II)> A CH₂Cl₂ suspension of p-Toluenesulfonyl Hydrazide (manufactured by Tokyo Chemical Industry Co., Ltd., 18.6 g) and p-Toluenesulfonyl Chloride (manufactured by Tokyo Chemical Industry Co., Ltd., 28.6 g) was placed in a 300 mL three-necked flask equipped with a thermometer and cooled in an ice bath. A mixed solution of Pyridine / CH₂Cl₂ = 1:1 (25 mL) was added dropwise over about 10 minutes using a dropping funnel while maintaining the internal temperature at 20 °C or lower. The reaction mixture was stirred at room temperature for 3 hours. Et₂O (diethyl ether) (60 mL) was added and the mixture was poured into a 1 L beaker. 60 mL of pure water and 60 mL of Et₂O were added in this order, and the mixture was stirred at room temperature for 10 minutes. The white precipitate was collected by filtration, transferred into a 500 mL eggplant flask, and dried under reduced pressure. MeOH (methanol) (260 mL) was added to the crude product, and the mixture was stirred for 3 hours while gently refluxing at a bath temperature of 80 °C. The mixture was cooled to room temperature, and the white precipitate was collected by filtration and washed with MeOH (90 mL) and Et₂O (90 mL). The obtained solid was dried under reduced pressure, and 26.9 g of a white solid was obtained. 1 H and 13 From the ¹H and ¹³C NMR spectra, it was confirmed that the obtained white solid was Ts-NHNH-Ts (Ts: tosyl group), which corresponds to the above-mentioned Compound (II). The yield was 79%.

[0071] <Vinyl Group Introduction Step> Into a 1 L three-necked flask equipped with a thermometer, add NaHCO3 (sodium hydrogen carbonate) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., 39.6 g), 3-Butene-1-ol (corresponding to the specific alcohol described above. Here, R is -CH2CH2-) (manufactured by Tokyo Chemical Industry Co., Ltd., 13.5 mL) and acetonitrile (400 mL), and cool in an ice bath. To this mixture, Bromoacetyl bromide (corresponding to the above compound (III). Here, X1 and X2 are bromine atoms) (manufactured by Tokyo Chemical Industry Co., Ltd., 20 mL) was added dropwise using a dropping funnel over about 1 hour while maintaining the internal temperature at 4 - 5 °C. After stirring at the same temperature for an additional about 30 minutes, the disappearance of 3-Butene-1-ol was confirmed by TLC (thin layer chromatography). Put pure water (500 mL) into a 3 L beaker and pour the obtained reaction solution while stirring. Wash the reaction vessel with pure water and then a small amount of acetonitrile, and add the washed liquid to the mixture. After stirring the mixture at room temperature for about 5 minutes, extract with CH2Cl2 (600 mL). Put the mixture into a 2 L separatory funnel, extract with CH2Cl2 (600 mL), and wash the CH2Cl2 layer with brine. Dry the CH2Cl2 layer over anhydrous magnesium sulfate, filter, and then concentrate under reduced pressure. The oily residue was dried under reduced pressure to obtain 28.6 g of a colorless oily product. Of the reaction product 1 H and 13 From the 1H and 13C NMR spectra, it was confirmed that the obtained oily product was the above compound (IV) (here, R is -CH2CH2- and X is a bromine atom). The yield was 94%.

[0072] <Hydrosilylation step> Into a 500 mL three-necked flask equipped with a thermometer, [IrCl(C8H 12)]2 (manufactured by Fujifilm Wako Pure Chemical Industries, 0.955 g) was placed, and the reaction vessel was evacuated and purged with nitrogen. Anhydrous CH2Cl2 (148 mL) was added, and the reaction vessel was cooled in an ice bath. While maintaining an internal temperature of 3 - 4 °C, triethoxysilane (corresponding to the above-described compound (VI). Here, R1, R2, and R3 are ethoxy groups) (manufactured by Tokyo Chemical Industry Co., Ltd., 32 mL) was added dropwise over approximately 30 minutes using a dropping funnel. Subsequently, a CH2Cl2 solution (15 mL) of the compound (IV) (28.6 g) synthesized as described above was added dropwise over approximately 1 hour using a dropping funnel. The mixture was stirred at the same temperature for about 30 minutes, and the disappearance of the compound (IV) was confirmed by TLC. In a 3 L beaker, SiO2 (114 g) was suspended in 500 mL of a mixed solution of AcOEt (ethyl acetate) / n-hexane = 20 / 80, cooled in an ice bath with stirring, and the reaction solution was slowly and gently poured into it. A 15 cm Kiriyama funnel was attached to a 3 L suction flask, and Celite (Celite No. 545 of Fujifilm Wako Pure Chemical Industries, Ltd.) was spread on the filter paper of the Kiriyama funnel, and the Celite was pressed firmly while suctioning to form a celite pad of about 1 cm. The quenched reaction mixture was filtered through the celite pad to separate SiO2 and insoluble substances. The filtrate was washed with 500 mL of a mixed solution of AcOEt / n-hexane = 20 / 80 and then 600 mL of a mixed solution of AcOEt / n-hexane = 30 / 70. The filtrate was concentrated under reduced pressure to obtain approximately 46 g of a pale brown oily crude product. The crude product was purified by column chromatography to obtain 42.46 g of a pale yellow oily product.

[0073] (Column conditions for purifying the crude product) ·Yamazen Smart Flash EPLC AI 580S ·Column Size 4L (SiO2 200 g), injection column 2L ·AcOEt / n-hexane = 0 / 100 → 9 / 91 ·UV 254 nm

[0074] 1 H, 13 C and 29From the Si NMR spectrum, it was confirmed that the obtained oily substance was the above-mentioned compound (VII) (where A is -CH2CH2CH2CH2-, R1, R2 and R3 are ethoxy groups, and X is a bromine atom). The yield was 80%.

[0075] <Diazoation process> A thermometer was attached, and the compound (VII) synthesized as described above was placed in a 100 mL three-necked flask under reduced pressure and purged with nitrogen. It was dissolved in 12 mL of anhydrous THF (tetrahydrofuran), and Ts-NHNH-Ts (1.59 g) synthesized as described above was added through a powder funnel. This was cooled to -10 °C, and a solution of tetramethylguanidine (manufactured by Tokyo Chemical Industry Co., Ltd., 32 mL) in anhydrous THF (1.3 mL) was added dropwise over about 20 minutes using a dropping funnel while maintaining the internal temperature at -5 to -3 °C. At the start of the dropwise addition, Ts-NHNH-Ts was not completely dissolved and was in a suspension state, but as the dropwise addition proceeded, it all dissolved once to form a uniform solution, and then white precipitates gradually formed. While maintaining the cooling at the same temperature, it was stirred for about another 20 minutes, and it was confirmed by TLC that the raw materials had almost disappeared. The reaction mixture was removed from the cooling device and stirred for about 1 hour while naturally warming to room temperature. The reaction mixture was a yellow solution containing white precipitates. The disappearance of the product of compound (VII) was confirmed by TLC, and Et2O (50 mL) was added to the reaction solution. SiO2 (5 g) was spread on a Kiriyama funnel and the reaction mixture was filtered. The filtrate was washed 4 times with 15 mL of Et2O. The filtrate and the washing solutions were combined and concentrated under reduced pressure, and the residue was purified by a SiO2 column. In this way, 0.674 g of a yellow oily substance was obtained.

[0076] (Column conditions for purifying the crude product) ·Yamazen Smart Flash EPLC AI 580S ·Column Size M (SiO2 16 g), injection column S ·AcOEt / n-hexane = 0 / 100 → 17 / 83 ·UV 254 nm

[0077] 1H, 13 C and 29 From the H, C, and Si NMR spectra, it was confirmed that the obtained oily substance was the above-described compound (I) (where A is -CH2CH2CH2CH2- and R1, R2, and R3 are ethoxy groups) (specific silane coupling agent). The yield was 52%.

[0078] [Example 2] <Synthesis of Compound (II)> Compound (II) was synthesized according to the same procedure as in Example 1.

[0079] <Vinyl Group Introduction Step> Compound (IV) was synthesized according to the same procedure as in Example 1.

[0080] <Diazoation Step> The reaction was carried out according to the same procedure as in the diazoation step of Example 1, except that the above-synthesized compound (IV) was used instead of compound (VII) and diazabicycloundecene was used instead of tetramethylguanidine, to obtain an oily substance. 1 H and 13 From the H and C NMR spectra, it was confirmed that the obtained oily substance was the above-described compound (V) (where R is -CH2CH2-).

[0081] <Hydrosilylation Step> The reaction was carried out according to the same procedure as in the hydrosilylation step of Example 1, except that the above-synthesized compound (V) was used instead of compound (IV) and Karstedt catalyst was used instead of iridium catalyst, to obtain an oily substance. 1 H, 13 C and 29 From the H, C, and Si NMR spectra, it was confirmed that the obtained oily substance was the above-described compound (I) (where A is -CH2CH2CH2CH2- and R1, R2, and R3 are ethoxy groups) (specific silane coupling agent).

[0082] [Example 3] Instead of triethoxysilane, methyldiethoxysilane (corresponding to the above-mentioned compound (VI), where two of R1, R2 and R3 are ethoxy groups and one is a methyl group) was used, and each step was carried out according to the same procedure as in Example 1 to obtain an oily substance. 1 H, 13 C and 29 From the 1H, 13C and 29Si NMR spectra, it was confirmed that the obtained oily substance was the above-mentioned compound (I) (where A is -CH2CH2CH2CH2-, and two of R1, R2 and R3 are ethoxy groups and one is a methyl group) (specific silane coupling agent). The yield (diazotization step) was 51%.

[0083] [Example 4] [Synthesis of compound (II)] Compound (II) was synthesized according to the same procedure as in Example 1.

[0084] [Vinyl group introduction step] Compound (IV) was synthesized according to the same procedure as in Example 1.

[0085] [Diazotization step] Using the compound (IV) synthesized as described above instead of compound (VII) and using 1,8-diazabicyclo[5.4.0]undec-7-ene instead of tetramethylguanidine, the reaction was carried out according to the same procedure as the diazotization step of Example 1 to obtain an oily substance. 1 H and 13 From the 1H and 13C NMR spectra, it was confirmed that the obtained oily substance was the above-mentioned compound (V) (where R is -CH2CH2-).

[0086] [Hydrosilylation step] Instead of the compound (IV), the compound (V) synthesized as described above was used. Instead of the iridium catalyst, the Karstedt catalyst was used. Instead of triethoxysilane, methyldiethoxysilane (corresponding to the compound (VI) described above. Here, two of R1, R2, and R3 are ethoxy groups and one is a methyl group) was used. The reaction was carried out according to the same procedure as the hydrosilylation step in Example 1, except for the above points, to obtain an oily substance. 1 H, 13 C and 29 From the Si NMR spectrum, it was confirmed that the obtained oily substance was the above-mentioned compound (I) (where A is -CH2CH2CH2CH2-, and two of R1, R2, and R3 are ethoxy groups and one is a methyl group) (specific silane coupling agent). The yield (hydrosilylation step) was 2%.

[0087] In Example 4 corresponding to Method 2 of the present invention, the yield of the specific silane coupling agent was 1%. In contrast, in Example 3 corresponding to Method 1 of the present invention, the yield of the specific silane coupling agent was 22%. Example 3 corresponding to Method 1 of the present invention showed a higher yield compared to Example 4 corresponding to Method 2 of the present invention.

Claims

【Claim 1】 The following compound (III) and CH ２ A vinyl group introduction step of synthesizing the following compound (IV) by reacting with a compound represented by =CH-R-OH (wherein R represents a divalent aliphatic hydrocarbon group or aromatic hydrocarbon group having 1 to 24 carbon atoms, which may have a hetero atom and may have a substituent), and A hydrosilylation step of synthesizing the following compound (VII) by reacting the compound (IV) with the following compound (VI) using an iridium catalyst, and A method for producing a silane coupling agent, comprising a diazotization step of synthesizing a silane coupling agent represented by the following compound (I) by reacting the following compound (II) with the compound (VII). 【Chemical Formula 1】 Compound (III) In the compound (III), X １ and X ２ each independently represents a halogen atom. 【Chemical Formula 2】 Compound (IV) In the compound (IV), R represents a divalent aliphatic hydrocarbon group or aromatic hydrocarbon group having 1 to 24 carbon atoms, which may have a hetero atom and may have a substituent, and X represents a halogen atom. 【Chemical Formula 3】 Compound (VI) In the compound (VI), R １ , R ２ and R ３ each independently represents a substituent. However, at least one of R １ , R ２ and R ３ is an alkoxy group. 【Chemical Formula 4】 Compound (VII) In the compound (VII), A represents a divalent aliphatic hydrocarbon group or aromatic hydrocarbon group having 3 to 26 carbon atoms, which may have a hetero atom and may have a substituent, and R １ , R ２ and R ３ The definition of R １ , R ２ and R ３ The definition of X is the same as that of X in compound (IV). [C5] Compound (II) In compound (II), Ts represents a tosyl group. [C6] Compound (I) In compound (I), the definition of A is the same as that of compound (VII), R １ , R ２ and R ３ The definition of R １ , R ２ and R ３ is the same as:

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