Hydrogen silane composition and method or producing hydrosilylation reactant

Abstract

The present invention provides a hydrogen silane composition which contains a mixture of a hydrogen silane compound represented by general formula (1) and an acid amide compound. (In the formula, each R1 independently represents a hydrogen atom, a halogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms; each R2 independently represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms; and n represents an integer of 0 to 2.)

Description

Method for producing hydrogensilane composition and hydrosilylation reactant

[0001] The present invention relates to a method for producing a hydrogensilane composition and a hydrosilylation reactant.

[0002] Hydrogensilane compounds having a hydrogen atom bonded to a silicon atom are useful as organic synthesis intermediates because they can be used to synthesize various organosilicon compounds by hydrosilylation reactions with organic compounds having unsaturated bonds such as vinyl groups, carbonyl groups, and imino groups, or by dehydrocondensation reactions with organic compounds having active hydrogen groups such as hydroxyl groups and primary or secondary amino groups. Furthermore, because they can be used in reduction reactions with various organic compounds, they are also useful as reducing agents with a wide range of applications.

[0003] Among the above-mentioned hydrogensilane compounds, hydrogensilane compounds having hydrolyzable silyl groups have silanol groups formed by hydrolysis of the hydrolyzable silyl groups, which form covalent bonds with hydroxyl groups on the surface of inorganic materials, thereby forming strong bonds with the inorganic materials. Furthermore, organosilicon compounds formed by the hydrosilylation reaction of these hydrogensilane compounds have organic groups that react with the organic materials, thereby enabling the bonding of organic and inorganic materials that are normally difficult to bond. This can impart properties to organic-inorganic composite materials, such as heat resistance, water resistance, weather resistance, improved mechanical strength, adhesion, dispersibility, hydrophobicity, and rust resistance. Taking advantage of these properties, the above-mentioned organosilicon compounds are used in a wide range of fields and applications, such as silane coupling agents, resin additives, surface treatment agents, fiber treatment agents, adhesives, paint additives, and polymer modifiers. Examples of such hydrogen silane compounds having a hydrolyzable silyl group include hydrogen halosilane compounds such as trichlorosilane and dichloromethylsilane (Patent Document 1), and hydrogen alkoxysilane compounds such as trimethoxysilane and dimethoxymethylsilane (Patent Document 2).

[0004] JP-A-8-151388 JP-A-57-118592

[0005] However, the hydrogen halosilane compound described in Patent Document 1 generates highly corrosive hydrogen halide upon hydrolysis of the halosilyl group. Methods for treating this hydrogen halide include, for example, reacting it with a basic compound such as amine, urea, or metal alkoxide to form an amine salt, urea salt, or metal salt. However, these salts are problematic because they are discharged as waste. In recent years, waste reduction has been identified as a major theme in the Sustainable Development Goals (SDGs). The hydrogen halosilane compound generates a large amount of hydrogen halide, raising concerns about its environmental impact. Furthermore, the basic compound is an expensive chemical product. Furthermore, the salt generated by the reaction with the hydrogen halide must be removed by filtration, separation, or other methods, complicating the process and reducing productivity.

[0006] In this regard, in the case of the hydrogenalkoxysilane compound described in Patent Document 2, an alcohol is generated by hydrolysis of the alkoxysilyl group, but this alcohol can be easily recovered and reused by methods such as distillation or extraction, making the process simple and providing excellent productivity. Furthermore, this hydrogenalkoxysilane compound has the advantage that the ionic impurities contained in the organosilicon compound synthesized by the hydrosilylation reaction or dehydration condensation reaction are reduced compared to hydrogenhalosilane compounds.

[0007] However, the hydrogenalkoxysilane compounds described in Patent Document 2 have inferior reactivity compared to hydrogenhalosilane compounds, resulting in problems of reduced reaction selectivity and reaction rate. Specifically, the hydrosilylation reaction of hydrogenalkoxysilane compounds promotes the transfer of double bonds in organic compounds having unsaturated bonds, thereby reducing the reaction selectivity of silyl groups to double bonds. Furthermore, the steric hindrance of the alkoxy groups reduces the reaction rate. This results in the production of large amounts of structural isomers of low-reactivity raw material compounds and addition isomers with different addition positions, which are by-products of the hydrosilylation reaction. Furthermore, hydrogenalkoxysilane compounds, which contain hydrogen atoms and alkoxy groups bonded to silicon atoms in their molecules, are highly self-reactive and prone to purity loss and chemical changes due to disproportionation and dehydrogenation reactions. Therefore, a decrease in the reaction rate of the hydrosilylation reaction leads to the promotion of disproportionation and dehydrogenation reactions, thereby increasing the number of by-products due to these side reactions.

[0008] Methods for improving the reaction selectivity and reaction rate of the hydrosilylation reaction of a hydrogenalkoxysilane compound include adding a carboxylic acid compound, an ammonium salt, etc. On the other hand, methods for mitigating the disproportionation reaction and dehydrogenation reaction include adding an amine compound, a carboxylic acid salt, etc.

[0009] However, in the case of carboxylic acid compounds, the hydroxyl groups of the carboxylic acid compound react with the hydrogen atoms or alkoxy groups of the hydrogenalkoxysilane compound. In the case of ammonium salts, the ammonium salt decomposes due to the heat of reaction, generating ammonia. These additives interact with the hydrosilylation catalyst to improve reaction selectivity and reaction rate, but if the reaction or decomposition occurs and the structure changes, the effect is lost. In the case of amine compounds, they act as catalyst poisons for the hydrosilylation catalyst and cannot be used in hydrosilylation reactions. In the case of carboxylic acid salts, because they are solids with low compatibility with hydrogenalkoxysilane compounds, their effect of mitigating disproportionation and dehydrogenation reactions is limited to the area in contact with the solid surface. Furthermore, the above additives each exhibit their own effect, and none of them can simultaneously improve reaction selectivity and reaction rate and mitigate disproportionation and dehydrogenation reactions.

[0010] Therefore, there has been a need for the development of a hydrogensilane composition that can increase the reactivity of a hydrogensilane compound in a hydrosilylation reaction, improve the reaction selectivity and reaction rate, and mitigate the disproportionation reaction and dehydrogenation reaction.

[0011] The present invention has been made in view of the above circumstances, and an object of the present invention is to provide a method for producing a hydrogensilane composition and a hydrosilylation reaction product that can increase the reactivity of a hydrogensilane compound in a hydrosilylation reaction, improve reaction selectivity and reaction rate, and mitigate disproportionation reactions and dehydrogenation reactions.

[0012] The present inventors conducted extensive research to solve the above-mentioned problems and found that the self-reactivity of a hydrogensilane compound is reduced by interaction with an acid amide compound, thereby reducing the decrease in purity, mitigating chemical changes and resulting in stable properties, and mitigating disproportionation and dehydrogenation reactions. They also found that the acid amide compound that has interacted with a hydrogensilane compound increases the reactivity of the hydrogensilane compound by interacting with a hydrosilylation reaction catalyst, thereby improving reaction selectivity and reaction rate, and thus completed the present invention.

[0013] That is, the present invention provides: 1. a hydrogensilane composition containing a mixture of a hydrogensilane compound represented by the following general formula (1) and an acid amide compound; (In the formula, R 1 each independently represents a hydrogen atom, a halogen atom, or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms; R 2 each independently represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, and n is an integer of 0 to 2. 2. The hydrogen silane composition according to 1, wherein the acid amide compound is an acid amide compound represented by the following general formula (2): (In the formula, R 3 is a k-valent unsubstituted hydrocarbon group having 1 to 30 carbon atoms which may contain a hydrogen atom or a heteroatom, and R 4 are hydrogen atoms or unsubstituted monovalent hydrocarbon groups having 1 to 30 carbon atoms, and may be the same or different. k is 1 or 2. 3. The hydrogen silane composition according to 2, wherein the acid amide compound is formamide or N-methylformamide; 4. The hydrogen silane composition according to any one of 1 to 3, wherein the content of the acid amide compound relative to the hydrogen silane compound is 0.0001 to 1 mass %; 5. The hydrogen silane composition according to any one of 1 to 4, wherein the content of the silane compound represented by the following general formula (3) is 0.001 to 2 mass % relative to the hydrogen silane compound; (In the formula, R 1 and R 2 has the same meaning as above, and m is an integer of 0 to 4. 6. A method for producing a hydrosilylation reactant, which comprises mixing the hydrogensilane composition according to any one of 1 to 5 with an organic compound having an unsaturated bond, and subjecting the hydrogensilane compound contained in the hydrogensilane composition and the organic compound having an unsaturated bond to a hydrosilylation reaction in the presence of a catalyst; 7. A method for producing a hydrosilylation reactant according to 6, in which the organic compound having an unsaturated bond is a compound containing, on average, one or more carbon-carbon double bonds or carbon-carbon triple bonds per molecule.

[0014] According to the present invention, the self-reactivity of the hydrogensilane compound is reduced by the interaction between the hydrogensilane compound and the acid amide compound, resulting in stable properties with reduced purity loss and chemical changes, and making it possible to mitigate disproportionation reactions and dehydrogenation reactions. Furthermore, in the hydrogensilane composition of the present invention, the acid amide compound that has interacted with the hydrogensilane compound interacts with the hydrosilylation reaction catalyst to increase the reactivity of the hydrogensilane compound, thereby improving reaction selectivity and reaction rate.

[0015] The present invention will be described in detail below. The hydrogen silane composition of the present invention contains a mixture of a hydrogen silane compound represented by the following general formula (1) (hereinafter referred to as "compound (1)") and an acid amide compound.

[0016]

[0017] In general formula (1), R 1 R each independently represents a hydrogen atom, a halogen atom, or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 8 carbon atoms. 1 Specific examples of the halogen atom in R include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. 1The monovalent hydrocarbon group may be linear, branched, or cyclic, and specific examples thereof include linear alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and n-decyl; sec-propyl, sec-butyl, tert-butyl, sec-pentyl, tert-pentyl, sec-hexyl, tert-hexyl, and sec-heptyl; Examples of such groups include branched alkyl groups such as butyl, tert-heptyl, sec-octyl, tert-octyl, sec-nonyl, tert-nonyl, sec-decyl, and tert-decyl groups; cyclic alkyl groups such as cyclopentyl and cyclohexyl groups; alkenyl groups such as vinyl, allyl, butenyl, and methallyl groups; aryl groups such as phenyl, tolyl, and xylyl groups; and aralkyl groups such as benzyl and phenethyl groups. Some or all of the hydrogen atoms in these monovalent hydrocarbon groups may be substituted with other substituents, and specific examples of such substituents include alkoxy groups having 1 to 3 carbon atoms such as methoxy, ethoxy, and (iso)propoxy groups; halogen atoms such as fluorine, chlorine, and bromine; aromatic hydrocarbon groups such as phenyl groups; cyano groups; amino groups; ester groups; ether groups; carbonyl groups; acyl groups; and sulfide groups, and these groups may be used alone or in combination of two or more. The substitution positions of these substituents are not particularly limited, and the number of substituents is also not limited.

[0018] Among these, R 1 As the group, a hydrogen atom, a halogen atom, a substituted or unsubstituted linear, branched or cyclic alkyl group having 1 to 6 carbon atoms; an alkenyl group; an aryl group; or an aralkyl group is preferable, and particularly from the viewpoint of easy availability of the precursor raw material, a hydrogen atom, a halogen atom, an unsubstituted linear alkyl group having 1 to 3 carbon atoms; or an alkenyl group is more preferable, and a hydrogen atom, a chlorine atom, a methyl group, or an ethyl group is even more preferable.

[0019] In general formula (1), R 2 each independently represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms, and specific examples thereof include R 1Examples of the substituents include the same monovalent hydrocarbon groups as those exemplified above.

[0020] In general formula (1), n ​​is an integer of 0 to 2 (0, 1, or 2). In particular, when the hydrosilylation reaction product obtained by the hydrosilylation reaction described below is used as a silane coupling agent, a surface treatment agent, or the like, n is preferably 0 or 1 from the viewpoint of reacting with multiple hydroxyl groups on the surface of a substrate to enhance adhesion.

[0021] Specific examples of compound (1) include monohydrogensilane compounds such as trimethoxysilane, triethoxysilane, dimethoxymethylsilane, and diethoxymethylsilane; dihydrogensilane compounds such as dimethoxysilane, diethoxysilane, methoxymethylsilane, and ethoxymethylsilane; and trihydrogensilane compounds such as methoxysilane and ethoxysilane. These may be used alone or in combination of two or more.

[0022] Among these, trimethoxysilane, triethoxysilane, dimethoxymethylsilane, diethoxymethylsilane, dimethoxysilane, and diethoxysilane are preferred from the viewpoint of reacting with multiple hydroxyl groups on the surface of a substrate to enhance adhesion, particularly when the hydrosilylation reaction product obtained by the hydrosilylation reaction described below is used as a silane coupling agent, surface treatment agent, or the like.

[0023] On the other hand, as the acid amide compound, for example, an acid amide compound represented by the following general formula (2) (hereinafter referred to as "compound (2)") is preferred.

[0024]

[0025] In general formula (2), R 3 represents a k-valent unsubstituted hydrocarbon group having 1 to 30 carbon atoms, preferably 1 to 25 carbon atoms, more preferably 1 to 20 carbon atoms, and even more preferably 1 to 10 carbon atoms, which may contain a hydrogen atom or a heteroatom, where k represents 1 or 2.

[0026] R when k is 1 3The monovalent hydrocarbon group may be linear, branched, or cyclic, and specific examples thereof include linear alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and n-decyl; sec-propyl, sec-butyl, tert-butyl, sec-pentyl, tert-pentyl, sec-hexyl, tert-hexyl, and sec-heptyl; Examples of such monovalent hydrocarbon groups include branched alkyl groups such as cyclopentyl, tert-heptyl, sec-octyl, tert-octyl, sec-nonyl, tert-nonyl, sec-decyl, and tert-decyl groups; cyclic alkyl groups such as cyclopentyl and cyclohexyl groups; alkenyl groups such as vinyl, allyl, butenyl, and methallyl groups; aryl groups such as phenyl, naphthyl, tolyl, and xylyl groups; and aralkyl groups such as benzyl and phenethyl groups. These monovalent hydrocarbon groups may contain heteroatoms such as -O-, -S-, and -N- in the molecular chain.

[0027] R when k is 2 3The divalent hydrocarbon group may be linear, branched, or cyclic, and specific examples thereof include linear alkylene groups such as methylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, nonamethylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, and octadecylene; sec-propylene, sec-butylene, tert-butylene, sec-pentylene, tert-pentylene, sec-hexylene, tert-hexylene, sec-heptylene, tert-heptylene, sec-octylene, tert-octylene, sec-nonylene, and tert-nonylene. Examples of the alkylene group include branched alkylene groups such as ethylene, sec-decylene, tert-decylene, sec-undecylene, tert-undecylene, sec-dodecylene, tert-dodecylene, sec-tridecylene, tert-tridecylene, sec-tetradecylene, tert-tetradecylene, sec-pentadecylene, tert-pentadecylene, sec-hexadecylene, tert-hexadecylene, sec-heptadecylene, tert-heptadecylene, sec-octadecylene, and tert-octadecylene; cyclic alkylene groups such as cyclopropylene, cyclopentylene, and cyclohexylene; alkenylene groups such as vinylene; and arylene groups such as o-, m-, or p-phenylene.

[0028] Among these, R 3 As the alkyl group, a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms, or an alkenyl group having 2 to 20 carbon atoms is preferable, and from the viewpoint of easy availability of precursor materials, a hydrogen atom, a linear alkyl group having 1 to 10 carbon atoms, or a linear alkenyl group having 2 to 10 carbon atoms is more preferable.

[0029] In general formula (2), R 4 are each independently a hydrogen atom or an unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms, preferably 1 to 25 carbon atoms, more preferably 1 to 20 carbon atoms, and even more preferably 1 to 10 carbon atoms. Specific examples of this monovalent hydrocarbon group include R 3 Among these, R4 As the alkyl group, a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms, or a linear alkenyl group having 2 to 20 carbon atoms is preferable, and from the viewpoint of easy availability of precursor materials, a hydrogen atom, a linear alkyl group having 1 to 10 carbon atoms, or an alkenyl group having 2 to 10 carbon atoms is more preferable.

[0030] Specific examples of compound (2) include N-methylacetamide, N,N-dimethylacetamide, malonamide, succinamide, maleamide, fumaramide, phthalamide, isophthalamide, terephthalamide, N-methylformamide, N,N-dimethylformamide, oxamide, glutaramide, adipamide, acetamide, acrylamide, benzamide, 2-naphthamide, nicotinamide, isonicotinamide, 2-furamide, formamide, propionamide, propiolamide, butyramide, isobutyramide, hexanamide, cyclohexanecarboxamide, methacrylamide, palmitamide, stearamide, oleamide, erucamide, cinnamamide, etc. These may be used alone or in combination of two or more.

[0031] These are commercially available as reagents, and from the viewpoints of easy availability and co-catalyst effect, acetamide, formamide, N-methylacetamide, N,N-dimethylacetamide, N-methylformamide, malonamide, succinamide, maleamide, fumaramide, benzamide, propionamide, butyramide, palmitamide, stearamide, oleamide, and erucamide are preferred, and from the viewpoint of ease of interaction with the hydrogensilane compound, formamide and N-methylformamide are particularly preferred.

[0032] The content of compound (2) in the hydrogensilane composition is not particularly limited as long as it exhibits an interaction with compound (1) and reduces the self-reactivity of compound (1). From the viewpoint of productivity, however, the content of compound (2) is preferably 0.0001 to 1 mass%, more preferably 0.001 to 0.5 mass%, even more preferably 0.005 to 0.2 mass%, and still more preferably 0.01 to 0.1 mass%, relative to compound (1).

[0033] In the present invention, the disproportionation reaction or dehydrogenation reaction of compound (1) in the hydrogensilane composition is alleviated, and therefore the content of the silane compound represented by the following general formula (3) (hereinafter referred to as "compound (3)") produced by these reactions can be reduced.

[0034]

[0035] In general formula (3), R 1 and R 2 represents the same meaning as above. Furthermore, m is an integer of 0 to 4 (0, 1, 2, 3, or 4), but from the viewpoint of easy availability of precursor materials, 0, 1, 2, or 3 is preferred, and 0, 1, or 2 is more preferred.

[0036] Specific examples of compound (3) include tetraalkoxysilane compounds such as tetramethoxysilane and tetraethoxysilane; trialkoxysilane compounds such as trimethoxymethylsilane, triethoxymethylsilane, trimethoxysilane and triethoxysilane; dialkoxysilane compounds such as dimethoxydimethylsilane, diethoxydimethylsilane, dimethoxymethylsilane, diethoxymethylsilane, dimethoxysilane and diethoxysilane; and monoalkoxysilane compounds such as methoxymethylsilane, ethoxymethylsilane, methoxysilane and ethoxysilane. These may be used alone or in combination of two or more.

[0037] The content of compound (3) in the hydrogensilane composition is an indicator of the progress of the disproportionation reaction or dehydrogenation reaction of compound (1). From the viewpoint of reducing by-products in the hydrosilylation reaction of compound (1), the content of compound (3) is preferably 0.001 to 2 mass%, more preferably 0.005 to 1.5 mass%, even more preferably 0.01 to 1.2 mass%, and still more preferably 0.02 to 1 mass%, relative to compound (1).

[0038] The method for measuring the content of compound (3) is not particularly limited, and analytical means such as gas chromatography, ion chromatography, high-performance liquid chromatography, thin-layer chromatography, nuclear magnetic resonance spectroscopy (NMR), infrared spectroscopy (IR), and near-infrared spectroscopy (NIR) can be used, and among these, gas chromatography is preferred.

[0039] The hydrogensilane composition of the present invention is obtained by mixing compound (1) and compound (2). The method for producing the mixture of compound (1) and compound (2) is not particularly limited, and compound (2) may be added to compound (1), or compound (1) may be added to compound (2). However, from the viewpoint of solubility, it is preferable to add compound (2) to compound (1). The mixing temperature is not particularly limited, and is preferably 20 to 50°C, and more preferably 20 to 40°C. The mixing time is also not particularly limited, and is preferably 30 minutes to 3 hours, and more preferably 30 minutes to 2 hours.

[0040] In the present invention, the acid amide compound that has interacted with the hydrogensilane compound in the hydrogensilane composition thus obtained interacts with the hydrosilylation reaction catalyst, thereby increasing the activity of the hydrosilylation reaction and improving the reaction selectivity and reaction rate.

[0041] Next, a method for producing a hydrosilylation reaction product of the present invention will be described. In the present invention, a hydrogensilane composition containing a mixture of compound (1) and compound (2) is mixed with an organic compound having an unsaturated bond (hereinafter referred to as "compound (4)"), and compound (1) contained in the hydrogensilane composition and compound (4) are subjected to a hydrosilylation reaction in the presence of a catalyst to produce a hydrosilylation reaction product.

[0042] Compound (4) is preferably a compound containing an average of one or more carbon-carbon double bonds or carbon-carbon triple bonds per molecule, and can be appropriately selected from known compounds. Specific examples thereof include ethylene, acetylene, propene, 1-propyne, 1-butene, 1-hexene, 2-hexene, 1-hexyne, 1-octene, 2-octene, 1-octyne, 1-decene, 2-decene, 1-decyne, 1-dodecene, 2-dodecene, 1-dodecyne, 1-tetradecene, 2-tetradecene, 1-tetradecyne, 1-hexadecene, 2-hexadecene, 1-hexadecene, 1-octadecene, 2-octadecene, and 1-octyne. Straight-chain hydrocarbon compounds having 2 to 20 carbon atoms, such as tadesine, 1-nonadecene, 2-nonadecene, 1-nonadesine, 1-eicosene, 2-eicosene, 1-eicosine, 1,5-hexadiene, 1,7-octadiene, and 1,9-decadiene; isobutene, 2-methyl-1-butene, 3-methyl-1-butene, 2-methyl-1-pentene, 3-methyl-1-pentene, 4-methyl-1-pentene, 2-methyl-1-hexene, and 3-methyl-1-hexene; branched hydrocarbon compounds having 3 to 8 carbon atoms, such as hexene, 4-methyl-1-hexene, 5-methyl-1-hexene, 2-methyl-1-heptene, 3-methyl-1-heptene, 4-methyl-1-heptene, 5-methyl-1-heptene, 6-methyl-1-heptene, and diisobutylene; cyclohexene, cyclooctene, styrene, divinylbenzene, norbornene, norbornadiene, cyclooctadiene, dicyclopentadiene, vinylnorbornene, and the like; Cyclic hydrocarbon compounds having 6 to 14 carbon atoms, such as olefin and 1,1-diphenylethylene; epoxide compounds, such as allyl glycidyl ether, 7-octenyl glycidyl ether, and vinylcyclohexene oxide; oxetane compounds, such as 3-ethyl-3-allyloxymethyloxetane; (meth)acrylate compounds, such as acrylic acid, methacrylic acid, methyl (meth)acrylate, allyl (meth)acrylate, and 7-octenyl (meth)acrylate;Organic halogen compounds such as allyl chloride, methallyl chloride, vinylbenzyl chloride, 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-octene, 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene, 1,4-divinyl(perfluoro)butane, 1,6-divinyl(perfluoro)hexane, 1,8-divinyl(perfluoro)oxane; vinyltrichlorosilane, vinyldichloromethylsilane, vinylchlorodimethylsilane, vinyltrimethoxysilane, vinyldimethoxymethylsilane, vinyl Nylmethoxydimethylsilane, vinyltriethoxysilane, vinyldiethoxymethylsilane, vinylethoxydimethylsilane, vinyl(tristrimethylsiloxy)silane, 3-(meth)acryloxypropyltrimethoxysilane, 3-(meth)acryloxypropyldimethoxymethylsilane, 3-(meth)acryloxypropylmethoxydimethylsilane, 3-(meth)acryloxypropyl(tristrimethylsiloxy)silane, 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, 1,3-divinyl-1,1,3,3-tetramethyl Organosilicon compounds such as disilazanes, bis(diethylamino)methylvinylsilanes, and N,N-bis(trimethylsilyl)allylamine; methyl vinyl ethers, divinyl ethers, phenyl vinyl ethers, allyl glycols, allyl benzyl ethers, diethylene glycol monoallyl ethers, diethylene glycol allyl methyl ethers, polyoxyethylene monoallyl ethers, polyoxypropylene monoallyl ethers, poly(oxyethylene-oxypropylene) monoallyl ethers, polyoxyethylene diallyl ethers, polyoxypropylene monoally ... ether compounds such as propylene diallyl ether and poly(oxyethylene-oxypropylene) diallyl ether; amine compounds such as allylamine, methallylamine, N-methylallylamine, N-ethylallylamine, N,N-dimethylallylamine, N,N-diethylallylamine, N-vinylpyrrolidone, N-allylaniline, N-allylmorpholine, N-allylpiperazine, N-allyl-N-methylpiperazine, 4-allyloxy-2,2,6,6-tetramethylpiperidine, and 4-allyloxy-1,2,2,6,6-pentamethylpiperidine;Examples of the compound include alcohol compounds such as allyl alcohol and methallyl alcohol; nitrile compounds such as acrylonitrile and methacrylonitrile; urea derivative compounds such as allyl isocyanate, triallyl isocyanurate and 1,3,4,6-tetraallylglycoluril; carbonate compounds such as diallyl carbonate; and acid anhydride compounds such as allyl succinic anhydride.

[0043] Among these, particularly when the resulting hydrosilylation reaction product is used as a silane coupling agent, surface treatment agent, or the like, from the viewpoint of reacting with organic groups in a substrate to impart properties such as improved heat resistance, water resistance, weather resistance, and mechanical strength, and adhesion, dispersibility, hydrophobicity, and rust prevention, linear hydrocarbon compounds, cyclic hydrocarbon compounds, epoxide compounds, (meth)acrylate compounds, organic halogen compounds, organic silicon compounds, ether compounds, amine compounds, urea derivative compounds, and acid anhydride compounds are preferred, linear hydrocarbon compounds, epoxide compounds, organic silicon compounds, amine compounds, and urea derivative compounds are more preferred, and linear hydrocarbon compounds having 1 to 10 carbon atoms, epoxide compounds, organic silicon compounds, and amine compounds are even more preferred.

[0044] The amount of compound (4) used is not particularly limited as long as it is an amount that allows the hydrosilylation reaction to proceed. From the viewpoints of reactivity and productivity, the amount is preferably 1 to 20 moles, more preferably 1 to 10 moles, and even more preferably 1 to 5 moles, per mole of compound (1).

[0045] The catalyst can be any known hydrosilylation reaction catalyst without any particular limitation, and can be appropriately selected from, for example, noble metal catalysts such as platinum, ruthenium, rhodium, palladium, iridium, etc.; base metal catalysts such as iron, cobalt, nickel, etc. Platinum catalysts are particularly preferred from the viewpoint of high reactivity.

[0046] The platinum catalyst can be appropriately selected from known platinum (Pt) catalysts and complex compounds containing platinum as the central metal. Specific examples include alcohol solutions of chloroplatinic acid, such as a 2-ethylhexanol solution of chloroplatinic acid (IV) acid; a toluene or xylene solution of a platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex; dichlorobisacetonitrile platinum, dichlorobisbenzonitrile platinum; and dichlorocyclooctadiene platinum. Catalysts in which platinum black or the like is supported on a support such as alumina, silica, or carbon can also be used. These catalysts may be used alone or in combination of two or more. Among these, alcohol solutions of chloroplatinic acid, such as a 2-ethylhexanol solution of chloroplatinic acid (IV) acid, and a toluene or xylene solution of a platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex are particularly preferred from the viewpoint of high reactivity.

[0047] The amount of platinum catalyst used is not particularly limited as long as it is an amount that exhibits a catalytic effect in the hydrosilylation reaction. From the viewpoints of reactivity and productivity, the amount of platinum metal used is preferably 0.0000001 to 1 mol, more preferably 0.000001 to 0.1 mol, and even more preferably 0.00001 to 0.01 mol per mol of compound (4).

[0048] When mixing the hydrogensilane composition with compound (4), compound (4) may be added to the hydrogensilane composition, or the hydrogensilane composition may be added to compound (4), but from the viewpoint of reaction selectivity or reaction rate of the hydrosilylation reaction, it is preferable to add the hydrogensilane composition to compound (4). Furthermore, the hydrosilylation reaction catalyst may be added at any time, but it is preferable to add the hydrosilylation reaction catalyst to compound (4) and then add the hydrogensilane composition.

[0049] The reaction temperature in the hydrosilylation reaction is not particularly limited, but from the viewpoints of reactivity and productivity, it is preferably 50 to 200° C., more preferably 50 to 150° C., and even more preferably 50 to 100° C. The reaction time in the hydrosilylation reaction is not particularly limited, but is preferably 1 to 30 hours, more preferably 1 to 20 hours, and even more preferably 1 to 10 hours.

[0050] The hydrosilylation reaction proceeds without a solvent, but can also be carried out in the presence of a solvent. Examples of the solvent include hydrocarbon solvents such as pentane, hexane, cyclohexane, heptane, isooctane, benzene, toluene, and xylene; ether solvents such as diethyl ether, tetrahydrofuran, and dioxane; ester solvents such as ethyl acetate and butyl acetate; aprotic polar solvents such as acetonitrile and N,N-dimethylformamide; and chlorinated hydrocarbon solvents such as dichloromethane and chloroform. These solvents may be used alone or in combination of two or more.

[0051] The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention is not limited to these examples. Note that the purity of the hydrogensilane compound shown below is a value measured under the following gas chromatography measurement condition 1, and the purity of the silane compound, which is the hydrosilylation reaction product obtained by the hydrosilylation reaction, is a value measured under the following gas chromatography measurement condition 2. [Gas chromatography measurement conditions 1] Gas chromatograph: GC-2014 (Shimadzu Corporation) Capillary column: DB-5, 0.25 mm x 30 m x 0.25 μm φ (Agilent Technologies, Inc.) Detector: FID Detector temperature: 300°C Injection port temperature: 280°C Heating program: 50°C (0 min) → 10°C / min → 200°C (0 min) Carrier gas: Helium (1.46 mL / min) Injection method: Split method Split ratio: 1 / 50 Injection amount: 1 μL [Gas chromatography measurement conditions 2] Gas chromatograph: GC-2014 (Shimadzu Corporation) Packed column: Silicone SE-30 (GL Sciences, Inc.) Detector: TCD Detector temperature: 300°C Injection port temperature: 300°C Temperature program: 70°C (0 min) → 10°C / min → 300°C (10 min) Carrier gas: Helium (50 mL / min) Injection amount: 1 μL

[0052] [1] Preparation of Hydrogensilane Composition [Example 1-1] 0.01 parts by mass of formamide was added to 100 parts by mass of dimethoxymethylsilane at room temperature (25°C, the same applies hereinafter), and the mixture was stirred at room temperature for 1 hour. At the beginning of stirring, the formamide was dispersed in the dimethoxymethylsilane, and after stirring was completed, the formamide was dissolved in the mixture, resulting in a homogeneous, colorless, transparent liquid dimethoxymethylsilane composition. Analysis of the resulting dimethoxymethylsilane composition by gas chromatography confirmed that the purity of the dimethoxymethylsilane was 99.68%.

[0053] Example 1-2: 0.05 parts by mass of formamide was added to 100 parts by mass of dimethoxymethylsilane at room temperature, and the mixture was stirred for 1 hour at room temperature. At the beginning of stirring, the formamide was dispersed in the dimethoxymethylsilane, and after stirring was completed, the formamide was dissolved in the mixture, resulting in a homogeneous, colorless, transparent liquid dimethoxymethylsilane composition. Analysis of the resulting dimethoxymethylsilane composition by gas chromatography confirmed that the purity of the dimethoxymethylsilane was 99.65%.

[0054] Example 1-3: 0.1 parts by mass of formamide was added to 100 parts by mass of dimethoxymethylsilane at room temperature, and the mixture was stirred for 1 hour at room temperature. At the beginning of stirring, the formamide was dispersed in the dimethoxymethylsilane, and after stirring was completed, the formamide was dissolved in the mixture, resulting in a homogeneous, colorless, transparent liquid dimethoxymethylsilane composition. Analysis of the resulting dimethoxymethylsilane composition by gas chromatography confirmed that the purity of the dimethoxymethylsilane was 99.62%.

[0055] [2] Stability Test of Hydrogensilane Composition [Example 2-1] 80 g of the dimethoxymethylsilane composition obtained in Example 1-1 was placed in a 100 mL perfluoroalkoxyalkane container (PFA container) that had been thoroughly substituted with nitrogen, sealed, and its stability was confirmed at 25 ° C. After 50 days, 100 days, and 150 days, the container was opened, and the dimethoxymethylsilane composition was analyzed by gas chromatography. The results are shown in Tables 1 and 2.

[0056] Example 2-2: 15 kg of the dimethoxymethylsilane composition obtained in Example 1-2 was placed in a 20 L SUS316 container that had been thoroughly purged with nitrogen, sealed, and its stability was confirmed at 25°C. After 15 days, 100 days, and 150 days, the container was opened, and the dimethoxymethylsilane composition was analyzed by gas chromatography. The results are shown in Tables 1 and 2.

[0057] [Example 2-3] 15 kg of the dimethoxymethylsilane composition obtained in Example 1-3 was placed in a 20 L SUS316 container that had been thoroughly purged with nitrogen, sealed, and its stability was confirmed at 25°C. After 15 days, 100 days, and 150 days, the container was opened, and the dimethoxymethylsilane composition was analyzed by gas chromatography. The results are shown in Tables 1 and 2.

[0058] Comparative Example 2-1: 80 g of formamide-free dimethoxymethylsilane was placed in a 100 mL PFA container that had been thoroughly purged with nitrogen, sealed, and its stability was confirmed at 25°C. After 50 days, 100 days, and 150 days, the container was opened, and the dimethoxymethylsilane was analyzed by gas chromatography. The results are shown in Tables 1 and 2.

[0059]

[0060]

[0061] [Example 2-4] 450 g of the dimethoxymethylsilane composition obtained in Example 1-2 was placed in a 500 mL SUS316 container whose atmosphere had been thoroughly purged with nitrogen, sealed, and its stability was confirmed at 50°C. After 26 days, the container was opened, and the dimethoxymethylsilane composition was analyzed by gas chromatography. The results are shown in Tables 3 and 4.

[0062] Comparative Example 2-2: 450 g of formamide-free dimethoxymethylsilane was placed in a 500 mL SUS316 container that had been thoroughly purged with nitrogen, sealed, and its stability was confirmed at 50°C. After 26 days, the container was opened, and the dimethoxymethylsilane composition was analyzed by gas chromatography. The results are shown in Tables 3 and 4.

[0063]

[0064]

[0065] As shown in Tables 1 to 4, in Examples 2-1 to 2-4, the dimethoxymethylsilane compositions prepared in Examples 1-1 to 1-3 exhibited reduced self-reactivity of the hydrogensilane compound due to the interaction between the hydrogensilane compound and the acid amide compound, and reduced the decrease in dimethoxymethylsilane purity. Furthermore, the low trimethoxymethylsilane content resulted in stable properties with reduced chemical changes, and the disproportionation and dehydrogenation reactions proceeded more slowly. The acid amide compound exhibits tautomerism, converting to the structure of an acid imide compound through tautomerization. This acid imide compound contains an imide group and a hydroxyl group that react with the hydrogensilane compound, and it is believed that the interaction between these substituents reduced the self-reactivity of the hydrogensilane compound.

[0066] On the other hand, in Comparative Examples 2-1 and 2-2, in which no acid amide compound was present, the disproportionation reaction and dehydrogenation reaction were accelerated, resulting in a decrease in the purity of dimethoxymethylsilane per unit time. The rate of purity decrease was particularly large when an accelerated test was performed by heating in Comparative Example 2-2. Furthermore, the trimethoxymethylsilane content was high, and the chemical change was not alleviated.

[0067] [3] Hydrosilylation Reaction 1 Using Hydrogensilane Composition [Example 3-1] Synthesis of n-Octyldimethoxymethylsilane 112.2 g (1.000 mol) of 1-octene and a 2-ethylhexanol solution of chloroplatinic(IV) acid (0.00003 mol as platinum atoms) were charged into a flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer at room temperature, and the raw material solution was heated over 0.5 hours to 70°C. After the internal temperature stabilized, 79.7 g (0.750 mol as dimethoxymethylsilane compound) of the dimethoxymethylsilane composition obtained in Example 1-2 was added dropwise to the raw material solution at 60-80°C over 5 hours, and the mixture was stirred at that temperature for 1 hour. The resulting reaction mixture was a homogeneous, brown, transparent liquid. Analysis of this reaction mixture by gas chromatography revealed the following area percentage ratio of the reaction mixture. The results are shown in Table 5.

[0068] Comparative Example 3-1 Synthesis of n-octyldimethoxymethylsilane A reaction was carried out in the same manner as in Example 3-1, except that 0.04 g of formamide (0.05 parts by mass per 100 parts by mass of dimethoxymethylsilane) was charged together with 1-octene and a 2-ethylhexanol solution of chloroplatinic(IV) acid, and then dimethoxymethylsilane containing no formamide was added dropwise. The resulting reaction mixture was a heterogeneous, brown, transparent liquid containing a brown solid. Analysis of this by gas chromatography revealed the following area percentage ratio of the reaction mixture. The results are shown in Table 5.

[0069] Comparative Example 3-2: Synthesis of n-octyldimethoxymethylsilane A reaction was carried out in the same manner as in Example 3-1, except that formamide-free dimethoxymethylsilane was used instead of the dimethoxymethylsilane composition. The resulting reaction mixture was a homogeneous, brown, transparent liquid, and when analyzed by gas chromatography, the area percentage ratio of the reaction mixture was found to be the following composition. The results are shown in Table 5.

[0070] A1 = dimethoxymethylsilane B1 = trimethoxymethylsilane C1 = 1-octene D1 = octene (structural isomer) E1 = n-octyldimethoxymethylsilane (addition isomer) F1 = n-octyldimethoxymethylsilane (target product)

[0071] Example 3-2 Synthesis of n-Octyltrimethoxysilane 0.05 parts by mass of formamide was added to 100 parts by mass of trimethoxysilane at room temperature, and the mixture was stirred for 1 hour at room temperature. At the beginning of stirring, formamide was dispersed in the trimethoxysilane, and after stirring was completed, the formamide was dissolved in the mixture, resulting in a uniform, colorless, transparent liquid trimethoxysilane composition. The reaction was carried out in the same manner as in Example 3-1, except that 91.7 g of the trimethoxysilane composition (0.750 mol as trimethoxysilane compound) was used instead of the dimethoxymethylsilane composition. The resulting reaction mixture was a uniform, brown, transparent liquid, and when analyzed by gas chromatography, the area percentage ratio of the reaction mixture was found to be the following composition. The results are shown in Table 6.

[0072] Comparative Example 3-3 Synthesis of n-octyltrimethoxysilane The reaction was carried out in the same manner as in Example 3-2, except that 0.05 g of formamide (0.05 parts by mass per 100 parts by mass of trimethoxysilane) was charged together with 1-octene and a 2-ethylhexanol solution of chloroplatinic (IV) acid, and then trimethoxysilane containing no formamide was added dropwise. The resulting reaction mixture was a heterogeneous, brown, transparent liquid containing a brown solid. Analysis of this by gas chromatography revealed the following area percentage ratio of the reaction mixture. The results are shown in Table 6.

[0073] Comparative Example 3-4: Synthesis of n-octyltrimethoxysilane A reaction was carried out in the same manner as in Example 3-2, except that formamide-free trimethoxysilane was used instead of the trimethoxysilane composition. The resulting reaction mixture was a homogeneous, brown, transparent liquid, and when analyzed by gas chromatography, the area percentage ratio of the reaction mixture was found to be the following composition. The results are shown in Table 6.

[0074] A2 = Trimethoxysilane B2 = Tetramethoxysilane C2 = 1-octene D2 = Octene (structural isomer) E2 = n-octyltrimethoxysilane (addition isomer) F2 = n-octyltrimethoxysilane (target product)

[0075] Example 3-3 Synthesis of n-Octyldiethoxymethylsilane To 100 parts by mass of diethoxymethylsilane, 0.05 parts by mass of formamide was added at room temperature, and the mixture was stirred for 1 hour. At the beginning of stirring, formamide was dispersed in the diethoxymethylsilane. After stirring was completed, the formamide dissolved in the mixture, resulting in a homogeneous, colorless, transparent liquid diethoxymethylsilane composition. The reaction was carried out in the same manner as in Example 3-1, except that 120.8 g of the diethoxymethylsilane composition (0.900 mol as diethoxymethylsilane compound) was used instead of the dimethoxymethylsilane composition. The resulting reaction mixture was a homogeneous, brown, transparent liquid. Analysis of this mixture by gas chromatography revealed the following area percentage ratio of the reaction mixture. The results are shown in Table 7.

[0076] Comparative Example 3-5 Synthesis of n-octyldiethoxymethylsilane A reaction was carried out in the same manner as in Example 3-3, except that 0.06 g of formamide (0.05 parts by mass per 100 parts by mass of diethoxymethylsilane) was charged together with 1-octene and a 2-ethylhexanol solution of chloroplatinic(IV) acid, and then diethoxymethylsilane containing no formamide was added dropwise. The resulting reaction mixture was a heterogeneous, brown, transparent liquid containing a brown solid. Analysis of this by gas chromatography revealed the following area percentage ratio of the reaction mixture. The results are shown in Table 7.

[0077] Comparative Example 3-6 Synthesis of n-octyltrimethoxysilane A reaction was carried out in the same manner as in Example 3-3, except that formamide-free diethoxymethylsilane was used instead of the diethoxymethylsilane composition. The resulting reaction mixture was a homogeneous, brown, transparent liquid, and when analyzed by gas chromatography, the area percentage ratio of the reaction mixture was found to be the following composition. The results are shown in Table 7.

[0078] A3 = diethoxymethylsilane B3 = triethoxymethylsilane C3 = 1-octene D3 = octene (structural isomer) E3 = n-octyldiethoxymethylsilane (addition isomer) F3 = n-octyldiethoxymethylsilane (target product)

[0079] Example 3-4 Synthesis of n-Octyltriethoxysilane 0.05 parts by mass of formamide was added to 100 parts by mass of triethoxysilane at room temperature, and the mixture was stirred for 1 hour at room temperature. At the beginning of stirring, formamide was dispersed in the triethoxysilane. After stirring was completed, the formamide was dissolved in the mixture, resulting in a uniform, colorless, transparent liquid triethoxysilane composition. The reaction was carried out in the same manner as in Example 3-1, except that 147.9 g of the triethoxysilane composition (0.900 mol as triethoxysilane compound) was used instead of the dimethoxymethylsilane composition. The resulting reaction mixture was a uniform, brown, transparent liquid. When analyzed by gas chromatography, the area percentage ratio of the reaction mixture was found to be the following composition. The results are shown in Table 8.

[0080] Comparative Example 3-7 Synthesis of n-octyltriethoxysilane A reaction was carried out in the same manner as in Example 3-4, except that 0.07 g of formamide (0.05 parts by mass per 100 parts by mass of triethoxysilane) was charged together with 1-octene and a 2-ethylhexanol solution of chloroplatinic(IV) acid, and then triethoxysilane containing no formamide was added dropwise. The resulting reaction mixture was a heterogeneous, brown, transparent liquid containing a brown solid. Analysis of this by gas chromatography revealed the following area percentage ratio of the reaction mixture. The results are shown in Table 8.

[0081] Comparative Example 3-8 Synthesis of n-octyltriethoxysilane A reaction was carried out in the same manner as in Example 3-4, except that formamide-free triethoxysilane was used instead of the triethoxysilane composition. The resulting reaction mixture was a homogeneous, brown, transparent liquid, and when analyzed by gas chromatography, the area percentage ratio of the reaction mixture was found to be the following composition. The results are shown in Table 8.

[0082] A4 = triethoxysilane B4 = tetraethoxysilane C4 = 1-octene D4 = octene (structural isomer) E4 = n-octyltriethoxysilane (addition isomer) F4 = n-octyltriethoxysilane (target product)

[0083] As shown in Tables 5 to 8, in Examples 3-1 to 3-4, the interaction between the hydrogensilane compound and the acid amide compound improved the reaction selectivity and reaction rate of the hydrosilylation reaction of the hydrogensilane compound, and suppressed the production of structural isomers of the less reactive starting compounds (D1 to D4 in the tables), thereby improving the yield of the target products (F1 to F4 in the tables).

[0084] On the other hand, in Comparative Examples 3-1, 3-3, 3-5, and 3-7, when the acid amide compound was present in the reaction system before interacting with the hydrogensilane compound, it acted as a catalytic poison for the hydrosilylation catalyst, preventing the reaction from proceeding and resulting in a reduced yield of the target product. Furthermore, the brown solid produced during the reaction contained the acid amide compound and the hydrosilylation catalyst, and the hydrosilylation catalyst had changed to a state in which it no longer exhibited catalytic activity. In Comparative Examples 3-2, 3-4, 3-6, and 3-8, when the acid amide compound was not present, the reaction selectivity and reaction rate of the hydrosilylation reaction of the hydrogensilane compound decreased, resulting in an increased number of structural isomers and a reduced yield of the target product.

[0085] [4] Hydrosilylation Reaction 2 Using Hydrogenalkoxysilane Composition [Example 4-1] Synthesis of 3-Glycidoxypropyldimethoxymethylsilane 114.1 g (1.000 mol) of allyl glycidyl ether and a 2-ethylhexanol solution of chloroplatinic(IV) acid (0.00001 mol as platinum atoms) were charged into a flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer at room temperature, and the raw material solution was heated over 0.5 hours to reach 70°C. After the internal temperature stabilized, 85.0 g (0.800 mol as dimethoxymethylsilane compound) of the dimethoxymethylsilane composition obtained in Example 1-2 was added dropwise to the raw material solution at 60-80°C over 5 hours, and the mixture was stirred at that temperature for 1 hour. The resulting reaction mixture was a homogeneous, brown, transparent liquid. Analysis of this reaction mixture by gas chromatography revealed the following area percentage ratio of the reaction mixture. The results are shown in Table 9.

[0086] Comparative Example 4-1 Synthesis of 3-glycidoxypropyldimethoxymethylsilane A reaction was carried out in the same manner as in Example 4-1, except that formamide-free dimethoxymethylsilane was used instead of the dimethoxymethylsilane composition. The resulting reaction mixture was a homogeneous, brown, transparent liquid, and when analyzed by gas chromatography, the area percentage ratio of the reaction mixture was found to be the following composition. The results are shown in Table 9.

[0087] A5 = dimethoxymethylsilane B5 = trimethoxymethylsilane C5 = allyl glycidyl ether D5 = propenyl glycidyl ether E5 = 2-glycidoxy-1-methyl-ethyldimethoxymethylsilane (addition isomer) F5 = 3-glycidoxypropyldimethoxymethylsilane (target product)

[0088] Example 4-2 Synthesis of 3-glycidoxypropyltrimethoxysilane To 100 parts by mass of trimethoxysilane, 0.05 parts by mass of formamide was added at room temperature, and the mixture was stirred for 1 hour at room temperature. At the beginning of stirring, formamide was dispersed in the trimethoxysilane, and after stirring was completed, the formamide was dissolved in the mixture, resulting in a uniform, colorless, transparent liquid trimethoxysilane composition. The reaction was carried out in the same manner as in Example 4-1, except that 85.0 g of the trimethoxysilane composition (0.800 mol as trimethoxysilane compound) was used instead of the dimethoxymethylsilane composition. The resulting reaction mixture was a uniform, brown, transparent liquid, and when analyzed by gas chromatography, the area percentage ratio of the reaction mixture was found to be the following composition. The results are shown in Table 10.

[0089] Comparative Example 4-2: Synthesis of 3-glycidoxypropyltrimethoxysilane A reaction was carried out in the same manner as in Example 4-2, except that formamide-free trimethoxysilane was used instead of the trimethoxysilane composition. The resulting reaction mixture was a homogeneous, brown, transparent liquid, and when analyzed by gas chromatography, the area percentage ratio of the reaction mixture was found to be the following composition. The results are shown in Table 10.

[0090] A6 = Trimethoxysilane B6 = Tetramethoxysilane C6 = Allyl glycidyl ether D6 = Propenyl glycidyl ether E6 = 2-glycidoxy-1-methyl-ethyltrimethoxysilane (addition isomer) F6 = 3-glycidoxypropyltrimethoxysilane (target product)

[0091] Example 4-3 Synthesis of 1-dimethoxymethylsilyl-2-trimethoxysilylethane A flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer was charged with 143.2 g (1.000 mol) of vinyltrimethoxysilane and a 2-ethylhexanol solution of chloroplatinic(IV) acid (0.00001 mol as platinum atoms) at room temperature, and the raw material solution was heated over 0.5 hours to reach 70°C. After the internal temperature stabilized, 85.0 g (0.800 mol as dimethoxymethylsilane compound) of the dimethoxymethylsilane composition obtained in Example 1-2 was added dropwise to the raw material solution at 60-80°C over 5 hours, and the mixture was stirred at that temperature for 1 hour. The resulting reaction mixture was a homogeneous, brown, transparent liquid. Analysis of this reaction mixture by gas chromatography revealed the following area percentage ratio of the reaction mixture. The results are shown in Table 11.

[0092] Comparative Example 4-3 Synthesis of 1-dimethoxymethylsilyl-2-trimethoxysilylethane A reaction was carried out in the same manner as in Example 4-3, except that formamide-free dimethoxymethylsilane was used instead of the dimethoxymethylsilane composition. The resulting reaction mixture was a homogeneous, brown, transparent liquid, and when analyzed by gas chromatography, the area percentage ratio of the reaction mixture was found to be the following composition. The results are shown in Table 11.

[0093] A7 = dimethoxymethylsilane B7 = trimethoxymethylsilane C7 = vinyltrimethoxysilane D7 = ethyltrimethoxysilane E7 = 1-dimethoxymethylsilyl-1-trimethoxysilylethane (addition isomer) F7 = 1-dimethoxymethylsilyl-2-trimethoxysilylethane (target product)

[0094] Example 4-4 Synthesis of N-phenyl-3-aminopropyltrimethoxysilane 0.05 parts by mass of formamide was added to 100 parts by mass of trimethoxysilane at room temperature, and the mixture was stirred for 1 hour at room temperature. At the beginning of stirring, the formamide dispersed in the trimethoxysilane, and after stirring was completed, the formamide dissolved in the mixture, resulting in a uniform, colorless, transparent liquid trimethoxysilane composition. A flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer was charged with 133.2 g (1.000 mol) of N-allylaniline and a toluene solution of platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (0.0001 mol as platinum atoms) at room temperature, and the raw material solution was heated over 0.5 hours until the temperature reached 70°C. After the internal temperature stabilized, 110.0 g of the trimethoxysilane composition (0.900 mol as trimethoxysilane compound) was added dropwise to the raw material solution over 5 hours at 60 to 80°C, and the mixture was stirred at that temperature for 1 hour. The resulting reaction mixture was a homogeneous, pale yellow, transparent liquid, and when analyzed by gas chromatography, the area percentage ratio of the reaction mixture was found to be the following composition. The results are shown in Table 12.

[0095] Comparative Example 4-4 Synthesis of N-phenyl-3-aminopropyltrimethoxysilane A reaction was carried out in the same manner as in Example 4-4, except that formamide-free trimethoxysilane was used instead of the trimethoxysilane composition. The resulting reaction mixture was a homogeneous, pale yellow, transparent liquid, and when analyzed by gas chromatography, the area percentage ratio of the reaction mixture was found to be the following composition. The results are shown in Table 12.

[0096] A8 = Trimethoxysilane B8 = Tetramethoxysilane C8 = N-Allylaniline D8 = N-Propenylaniline E8 = N-Phenyl-2-amino-1-methyl-ethyltrimethoxysilane (addition isomer) F8 = N-Phenyl-3-aminopropyltrimethoxysilane (target product)

[0097] As shown in Tables 9 to 12, in Examples 4-1 to 4-4, the interaction between the hydrogensilane compound and the acid amide compound improved the reaction selectivity of the hydrosilylation reaction of the hydrogensilane compound and suppressed the production of addition isomers (E5 to E8 in the tables) with different addition positions, which are by-products of the hydrosilylation reaction. Furthermore, the suppression of the production of structural isomers (D5 to D8 in the tables) of the less reactive raw material compounds improved the yield of the target products (F5 to F8 in the tables).

[0098] On the other hand, in Comparative Examples 4-1 to 4-4, when an acid amide compound was not present, the reaction selectivity of the hydrosilylation reaction of the hydrogensilane compound was low, resulting in a large amount of addition isomers and structural isomers, and a reduced yield of the target product.

Claims

1. A hydrogen silane composition comprising a mixture of a hydrogen silane compound represented by the following general formula (1) and an acid amide compound. 【Chemical 1】 (In the formula, R 1 each independently represents a hydrogen atom, a halogen atom, or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, and R 2 each independently represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, and n is an integer of 0 to 2.)

2. The hydrogen silane composition according to Claim 1, wherein the acid amide compound is an acid amide compound represented by the following general formula (2). 【Chemical Formula 2】 (wherein, R 3 is an optionally substituted k-valent hydrocarbon group having 1 to 30 carbon atoms which may contain a hydrogen atom or a hetero atom, and R 4 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 30 carbon atoms which is unsubstituted, and each may be the same or different. k is 1 or 2.)

3. The hydrogen silane composition according to Claim 2, wherein the acid amide compound is formamide or N-methylformamide.

4. The hydrogen silane composition according to Claim 1, wherein the content of the acid amide compound with respect to the hydrogen silane compound is 0.0001 to 1% by mass.

5. The hydrogen silane composition according to Claim 1, wherein the content of the silane compound represented by the following general formula (3) is 0.001 to 2% by mass with respect to the hydrogen silane compound. [Chemical Formula 3] (wherein R 1 and R 2 represent the same meaning as described above, and m is an integer of 0 to 4.)

6. A method for producing a hydrosilylation reaction product, comprising mixing the hydrogen silane composition according to any one of Claims 1 to 5 with an organic compound having an unsaturated bond, and subjecting the hydrogen silane compound contained in the hydrogen silane composition and the organic compound having an unsaturated bond to a hydrosilylation reaction in the presence of a catalyst.

7. The method for producing a hydrosilylation reaction product according to Claim 6, wherein the organic compound having an unsaturated bond is a compound containing an average of one or more carbon-carbon double bonds or carbon-carbon triple bonds per molecule.