Method for producing a hydrogensilane composition and hydrosilylated reaction product

Abstract

To provide a hydrogen silane composition that enhances the reactivity of hydrogen silane compounds in hydrosilylation reactions, improves reaction selectivity and reaction rate, and mitigates disproportionation and dehydrogenation reactions. [Solution] A hydrogensilane composition comprising a mixture of a hydrogensilane compound represented by the following general formula (1) and an acid amide compound (excluding compositions comprising an organic compound having an unsaturated bond containing an average of one or more carbon-carbon double bonds or carbon-carbon triple bonds per molecule). TIFF2026110850000022.tif7140 (in the formula, R 1 Each of these 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 of these independently represents a substituted or unsubstituted monovalent hydrocarbon group with 1 to 20 carbon atoms, and n is an integer between 0 and 2.

Description

[Technical Field]

[0001] This invention relates to a method for producing a hydrogen silane composition and a hydrosilylated reaction product. [Background technology]

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

[0003] Among the above-mentioned hydrogensilane compounds, those having hydrolyzable silyl groups have silanol groups generated by the hydrolysis of the hydrolyzable silyl groups that form covalent bonds with hydroxyl groups on the surface of inorganic materials, resulting in a strong bond with the inorganic material. Furthermore, organosilicon compounds produced by the hydrosilylation reaction of these hydrogensilane compounds enable the bonding of organic and inorganic materials, which are normally difficult to bond, through the reaction of organic groups with organic materials. This makes it possible to impart properties such as heat resistance, water resistance, weather resistance, improved mechanical strength, adhesion, dispersibility, hydrophobicity, and corrosion resistance to organic-inorganic composite materials. By utilizing these properties, the organosilicon compounds described above are used in a wide range of fields and applications, including silane coupling agents, resin additives, surface treatment agents, fiber treatment agents, adhesives, paint additives, and polymer modifiers. Examples of hydrogen silane compounds having such hydrolyzable silyl groups include hydrogen halosilane compounds such as trichlorosilane and dichloromethylsilane (Patent Document 1), and hydrogen alkoxysilane compounds such as trimethoxysilane and dimethylpsilane (Patent Document 2). [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Japanese Patent Application Publication No. 8-151388 [Patent Document 2] Japanese Patent Application Publication No. 57-118592 [Overview of the Initiative] [Problems that the invention aims to solve]

[0005] However, the hydrogen halosilane compound described in Patent Document 1 generates highly corrosive hydrogen halides through hydrolysis of the halosilyl group. Methods for treating these hydrogen halides include reacting them with basic compounds such as amines, urea, and metal alkoxides to form amine salts, urea salts, and metal salts, but these salts are problematic because they are discharged as waste. In recent years, waste reduction has been a major theme in the Sustainable Development Goals (SDGs), and the above-mentioned hydrogen halosilane compound generates a large amount of hydrogen halides, raising concerns about its environmental impact. Furthermore, the above-mentioned basic compounds are expensive chemicals, and the salts produced by their reaction with hydrogen halides must be removed by methods such as filtration or liquid-liquid separation, which complicates the process and reduces productivity.

[0006] In this regard, in the case of the hydrogen alkoxysilane compound described in Patent Document 2, alcohol is generated by the 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 offering excellent productivity. Furthermore, these hydrogen alkoxysilane compounds have the advantage of containing fewer ionic impurities in organosilicon compounds synthesized by hydrosilylation or dehydration condensation reactions compared to hydrogen halosilane compounds.

[0007] However, the hydrogen alkoxysilane compounds described in Patent Document 2 have lower reactivity compared to hydrogen halosilane compounds, resulting in problems with reduced reaction selectivity and reaction rate. In other words, the hydrosilylation reaction of hydrogen alkoxysilane compounds promotes the transfer of double bonds in organic compounds containing unsaturated bonds, thereby reducing the selectivity of the silyl group to the double bond. Furthermore, the steric hindrance of the alkoxy group slows down the reaction rate. As a result, many structural isomers of the less reactive starting compound and by-products of the hydrosilylation reaction, such as addition isomers at different positions, are produced. Furthermore, because hydrogen alkoxysilane compounds have hydrogen atoms bonded to silicon atoms and alkoxy groups in their molecules, they are extremely self-reactive and prone to depurity reduction and chemical changes through disproportionation and dehydrogenation reactions. Therefore, a decrease in the reaction rate of the hydrosilylation reaction leads to the acceleration of disproportionation and dehydrogenation reactions, which in turn exacerbates problems such as an increase in byproducts from these side reactions.

[0008] Methods to improve the reaction selectivity and reaction rate of the hydrosilylation reaction of hydrogen alkoxysilane compounds include adding carboxylic acid compounds, ammonium salts, etc. On the other hand, methods to mitigate disproportionation and dehydrogenation reactions include adding amine compounds, carboxylic acid salts, etc.

[0009] However, in the case of carboxylic acid compounds, the hydroxyl group of the carboxylic acid compound reacts with the hydrogen atom or alkoxy group of the hydrogenalkoxysilane compound. In the case of ammonium salts, the ammonium salt decomposes due to the heat of reaction, generating ammonia. These additives improve reaction selectivity and reaction rate by interacting with the hydrosilylation reaction catalyst, but if the above reactions or decomposition occur and the structure changes, they will no longer be able to exhibit these effects. In the case of amine compounds, they act as catalyst poisons for hydrosilylation reaction catalysts and therefore cannot be applied to hydrosilylation reactions. In the case of carboxylate salts, since they are solids with low miscibility with hydrogenalkoxysilane compounds, the effect of mitigating disproportionation and dehydrogenation reactions is limited to the portion in contact with the solid surface. Furthermore, each of the above additives exhibited its own effect individually, and it was not possible to achieve both improved reaction selectivity and reaction rate and mitigation of disproportionation and dehydrogenation reactions simultaneously.

[0010] Therefore, there has been a need for the development of a hydrogensilane composition that can enhance the reactivity of hydrogensilane compounds in hydrosilylation reactions, improve reaction selectivity and reaction rate, while mitigating disproportionation and dehydrogenation reactions.

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

[0012] The inventors of the present invention conducted extensive research to solve the above problems and found that the self-reactivity of the hydrogen silane compound decreases through interaction with the acid amide compound, resulting in reduced purity degradation, a more stable state with mitigated chemical changes, and mitigation of disproportionation and dehydrogenation reactions. Furthermore, they found that the acid amide compound, after interacting with the hydrogen silane compound, enhances the reactivity of the hydrogen silane compound through interaction with the hydrosilylation reaction catalyst, thereby improving reaction selectivity and reaction rate. Thus, the present invention was completed.

[0013] In other words, the present invention is 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 (however, excluding a composition containing an organic compound having an unsaturated bond containing an average of one or more carbon-carbon double bonds or carbon-carbon triple bonds per molecule), [Chemical formula] (In the formula, R , 2 , 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 from 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), [Chemical formula] (In the formula, R 3 is an unsubstituted k-valent hydrocarbon group having 1 to 30 carbon atoms that may contain a hetero atom, and R 4 is a hydrogen atom or an unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms, and each 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 with respect to the hydrogen silane compound is 0.0001 to 1% by 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% by mass with respect to the hydrogen silane compound, [Chemical formula] (In the formula, R 1 and R​​ 6. A method for producing a hydrosilylated product, comprising mixing a hydrogensilane composition described in any of 1 to 5 with an organic compound having an unsaturated bond, and then hydrosilylating the hydrogensilane compound contained in the hydrogensilane composition with the organic compound having an unsaturated bond in the presence of a catalyst. 7. A method for producing a hydrosilylated product according to 6, wherein the organic compound having the unsaturated bond is a compound containing an average of one or more carbon-carbon double bonds or carbon-carbon triple bonds per molecule. To provide. [Effects of the Invention]

[0014] According to the present invention, the interaction between the hydrogensilane compound and the acid amide compound reduces the self-reactivity of the hydrogensilane compound, resulting in stable properties with reduced purity and chemical changes, and mitigating disproportionation and dehydrogenation reactions. Furthermore, in the hydrogensilane composition of the present invention, the acid amide compound that interacts with the hydrogensilane compound enhances the reactivity of the hydrogensilane compound through interaction with the hydrosilylation reaction catalyst, thereby improving the reaction selectivity and reaction rate. [Modes for carrying out the invention]

[0015] The present invention will be described in detail below. The hydrogen silane composition of the present invention comprises 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] [ka]

[0017] In general formula (1), R 1Each 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, more preferably 1 to 8 carbon atoms. R 1 Specific examples of the halogen atom of 1 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R 1 The monovalent hydrocarbon group of 1 may be linear, branched, or cyclic. 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 groups; branched alkyl groups such as sec-propyl, sec-butyl, tert-butyl, sec-pentyl, tert-pentyl, sec-hexyl, tert-hexyl, sec-heptyl, 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; aralkyl groups such as benzyl and phenethyl groups, and the like. Note that some or all of the hydrogen atoms of these monovalent hydrocarbon groups may be substituted with other substituents. Specific examples of this substituent 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 group; cyano group; amino group; ester group; ether group; carbonyl group; acyl group; sulfide group, and the like. One or more of these can be used in combination. The substitution position of these substituents is not particularly limited, and the number of substituents is also not limited.

[0018] Among these, R 1Preferred members include hydrogen atoms, halogen atoms, substituted or unsubstituted linear, branched, or cyclic alkyl groups having 1 to 6 carbon atoms; alkenyl groups; aryl groups; and aralkyl groups. Particularly from the viewpoint of the availability of precursor raw materials, hydrogen atoms, halogen atoms, and unsubstituted linear alkyl groups having 1 to 3 carbon atoms; alkenyl groups are more preferred, and hydrogen atoms, chlorine atoms, methyl groups, and ethyl groups are even more preferred.

[0019] In general formula (1), R 2 Each of these independently represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms, and a specific example thereof is R 1 Examples of substituents similar to those exemplified by the monovalent hydrocarbon group include those mentioned above.

[0020] In general formula (1), n ​​is an integer between 0 and 2 (0, 1, or 2). In particular, when the hydrosilylated product obtained by the hydrosilylation reaction described later is used as a silane coupling agent or surface treatment agent, 0 or 1 is preferred from the viewpoint of reacting with multiple hydroxyl groups on the substrate surface to improve 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 individually or in combination of two or more.

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

[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] [ka]

[0025] In general formula (2), R 3 represents an 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, and k represents 1 or 2.

[0026] R when k is 1 3 The monovalent hydrocarbon group may be linear, branched, or cyclic. Specific examples 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 groups; branched alkyl groups such as sec-propyl, sec-butyl, tert-butyl, sec-pentyl, tert-pentyl, sec-hexyl, tert-hexyl, sec-heptyl, 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. Furthermore, these monovalent hydrocarbon groups may contain heteroatoms such as -O-, -S-, and -N- in their molecular chains.

[0027] R when k is 2 3The divalent hydrocarbon group may be linear, branched, or cyclic. Specific examples 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, sec-heptylene, tert-heptylene, sec-octylene, tert-octylene, sec-nonylene, and tert-nonylene. Examples include branched alkylene groups such as nylene, 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 groups; cyclic alkylene groups such as cyclopropylene, cyclopentylene, and cyclohexylene groups; alkenylene groups such as vinylene groups; and arylene groups such as o,m, or p-phenylene groups.

[0028] Among these, R 3 Preferably, the elements are a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms, or an alkenyl group having 2 to 20 carbon atoms. Particularly from the viewpoint of the availability of precursor raw 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 preferred.

[0029] In general formula (2), R 4 Each of these independently represents 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. A specific example of this monovalent hydrocarbon group is R 3Examples of substituents similar to those exemplified above include those found in the previous example. Among these, R 4 Preferably, the precursors are a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms, or a linear alkenyl group having 2 to 20 carbon atoms. Particularly from the viewpoint of the 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 preferred.

[0030] Specific examples of compound (2) include N-methylacetamide, N,N-dimethylacetamide, malonamide, succinamide, maleamide, fumaamide, phthalamide, isophthalamide, terephthalamide, N-methylformamide, N,N-dimethylformamide, oxamide, glutaramide, adipoamide, acetamide, acrylamide, benzamide, 2-naphthamide, nicotinamide, isonicotinamide, 2-fluamide, formamide, propionamide, propioamide, butylamide, isobutylamide, hexaneamide, cyclohexanecarboxamide, methacrylamide, palmitamide, stearamide, oleamide, erucamide, cinnamamide, etc. These may be used individually or in combination of two or more.

[0031] These are commercially available as reagents, and from the viewpoint of ease of availability and cocatalytic effect, acetamide, formamide, N-methylacetamide, N,N-dimethylacetamide, N-methylformamide, malonamide, succinamide, maleamide, fumaamide, benzamide, propionamide, butylamide, palmitoamide, stearamide, oleamide, and ercamamide are particularly preferred, and from the viewpoint of ease of interaction with hydrogen silane compounds, 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 interacts with compound (1) and reduces the self-reactivity of compound (1). However, from the viewpoint of productivity, it is preferably 0.0001 to 1% by mass, more preferably 0.001 to 0.5% by mass, even more preferably 0.005 to 0.2% by mass, and still even more preferably 0.01 to 0.1% by mass relative to compound (1).

[0033] In the present invention, the disproportionation reaction or dehydrogenation reaction of compound (1) in the above-mentioned hydrogen silane composition is mitigated, thereby reducing the content of the silane compound represented by the following general formula (3) (hereinafter referred to as "compound (3)") that is generated by these reactions.

[0034] [ka]

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

[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 individually 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 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% by mass, more preferably 0.005 to 1.5% by mass, even more preferably 0.01 to 1.2% by mass, and still more preferably 0.02 to 1% by mass, relative to compound (1).

[0038] There are no particular restrictions on the method for measuring the content of compound (3), and analytical methods 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 employed, with gas chromatography being preferred among them.

[0039] The hydrogen silane 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; 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, but is preferably 20 to 50°C, and more preferably 20 to 40°C. The mixing time is also not particularly limited, but 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 interacts with the hydrogen silane compound in the hydrogen silane composition obtained in this way interacts with the hydrosilylation reaction catalyst, thereby increasing the activity of the hydrosilylation reaction and improving the reaction selectivity and reaction rate.

[0041] Next, the method for producing the hydrosilylated reaction product of the present invention will be described. In the present invention, a hydrosilylated product can be produced by mixing a hydrogensilane composition containing a mixture of compound (1) and compound (2) with an organic compound having an unsaturated bond (hereinafter referred to as "compound (4)") and then performing a hydrosilylation reaction between compound (1) and compound (4) in the hydrogensilane composition in the presence of a catalyst.

[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 include ethylene, acetylene, propene, 1-propyne, 1-butene, 1-hexene, 2-hexene, 1-hexyne, 1-octene, 2-octene, 1-octine, 1-decene, 2-decene, 1-decine, 1-dodecene, 2-dodecene, 1-dodecine, 1-tetradecene, 2-tetradecene, 1-tetradecine, 1-hexadecene, 2-hexadecene, 1-hexadecene, 1-octadecene, 2-octadecene, 1-octadecine, 1-nonadecene, 2-nonadecene, 1-nonadecene, 1-eicosene, 2-eicosene Linear hydrocarbon compounds with 2 to 20 carbon atoms, such as 1-eicosine, 1,5-hexadiene, 1,7-octadiene, and 1,9-decadien; 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, 3-methyl-1-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 - Branched hydrocarbon compounds with 3-8 carbon atoms such as heptene and diisobutylene; cyclic hydrocarbon compounds with 6-14 carbon atoms such as cyclohexene, cyclooctene, styrene, divinylbenzene, norbornene, norbornadiene, cyclooctadiene, dicyclopentadiene, vinylnorbornene, 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-alyloxymethyloxetane; acrylic acid, methacrylic Acids, (meth)acrylate compounds such as methyl (meth)acrylate, allyl (meth)acrylate, and 7-octenyl (meth)acrylate; organic halogen compounds such as allyl chloride, methallyl chloride, vinyl benzyl 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, and 1,8-divinyl(perfluoro)oxane;Vinyltrichlorosilane, vinyldichloromethylsilane, vinylchlorodimethylsilane, vinyltrimethoxysilane, vinyldimethoxymethylsilane, vinylmethoxydimethylsilane, vinyltriethoxysilane, vinyldiethoxymethylsilane, vinylethoxydimethylsilane, vinyl(tritrimethylsiloxy)silane, 3-(meth)acryloxypropyltrimethoxysilane, 3-(meth)acryloxypropyldimethoxymethylsilane, 3-(meth)acryloxypropylmethoxydimethylsilane, 3-(meth)acryloxypropyl Organic silicon compounds such as pyr(tritrimethylsiloxy)silane, 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, 1,3-divinyl-1,1,3,3-tetramethyldisilazane, bis(diethylamino)methylvinylsilane, N,N-bis(trimethylsilyl)allylamine; methyl vinyl ether, divinyl ether, phenyl vinyl ether, allyl glycol, allyl benzyl ether, diethylene glycol monoallyl ether, diethylene glycol allyl methyl ether, polyoxyethylene monoallyl ether Ether compounds such as polyoxypropylene monoallyl ether, poly(oxyethylene-oxypropylene) monoallyl ether, polyoxyethylene diallyl ether, polyoxypropylene diallyl ether, poly(oxyethylene-oxypropylene) diallyl ether, allylamine, methallylamine, N-methylallylamine, N-ethylallylamine, N,N-dimethylallylamine, N,N-diethylallylamine, N-vinylpyrrolidone, N-allylaniline, N-allylmorpholine, N-allylpiperazine, N-allyl Examples include amine compounds such as -N-methylpiperazine, 4-allyloxy-2,2,6,6-tetramethylpiperidine, and 4-allyloxy-1,2,2,6,6-pentamethylpiperidine; alcohol compounds such as allyl alcohol and metharyl alcohol; nitrile compounds such as acrylonitrile and methacrylonitrile; urea derivative compounds such as allyl isocyanate, triallyl isocyanurate, and 1,3,4,6-tetraallyl glycoluryl; carbonate compounds such as diallyl carbonate; and acid anhydride compounds such as allyl succinic anhydride.

[0043] Among these, when the resulting hydrosilylated reaction product is used as a silane coupling agent or surface treatment agent, linear hydrocarbon compounds, cyclic hydrocarbon compounds, epoxide compounds, (meth)acrylate compounds, organic halogen compounds, organosilicon compounds, ether compounds, amine compounds, urea derivative compounds, and acid anhydride compounds are preferred from the viewpoint of reacting with the organic groups of the substrate to impart properties such as improved heat resistance, water resistance, weather resistance, mechanical strength, adhesion, dispersibility, hydrophobicity, and rust prevention. Linear hydrocarbon compounds, epoxide compounds, organosilicon compounds, amine compounds, and urea derivative compounds are more preferred, and linear hydrocarbon compounds, epoxide compounds, organosilicon compounds, and amine compounds having 1 to 10 carbon atoms 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, but from the viewpoint of reactivity and productivity, it 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] As a catalyst, any conventionally known hydrosilylation reaction catalyst can be used without particular limitations. For example, noble metal catalysts such as platinum, ruthenium, rhodium, palladium, and iridium; base metal catalysts such as iron, cobalt, and nickel can be appropriately selected and used. Platinum catalysts are particularly preferred from the viewpoint of high reactivity.

[0046] The platinum catalyst can be appropriately selected from known platinum (Pt) and platinum-centered complex compounds. Specific examples include alcoholic solutions of chloroplatinic acid, such as chloroplatinic acid and chloroplatinic acid(IV) in 2-ethylhexanol solution; toluene or xylene solution of platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex; dichlorobisacetonitrile platinum; dichlorobisbenzonitrile platinum; and dichlorocyclooctadiene platinum. Catalysts in which platinum black or similar materials are supported on a carrier such as alumina, silica, or carbon can also be used. These may be used individually or in combination of two or more. Among these, alcoholic solutions of chloroplatinic acid, such as a 2-ethylhexanol solution of chloroplatinic acid (IV), and toluene or xylene solutions of 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 the catalytic effect of the hydrosilylation reaction. However, from the viewpoint of reactivity and productivity, the amount of platinum metal used is preferably 0.0000001 to 1 mole, more preferably 0.000001 to 0.1 moles, and even more preferably 0.00001 to 0.01 moles per mole 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). However, 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 viewpoint 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 above hydrosilylation reaction can proceed without a solvent, but a solvent may also be used. Examples of solvents 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 individually or in combination of two or more. [Examples]

[0051] The present invention will be described more specifically below with reference to examples and comparative examples, but the present invention is not limited to the following examples. The purity of the following hydrogensilane compounds was measured under gas chromatography measurement condition 1, while the purity of the silane compounds obtained as hydrosilylated reaction products in the hydrosilylation reaction was measured under gas chromatography measurement condition 2. [Gas chromatography measurement conditions 1] Gas chromatograph: GC-2014 (manufactured by Shimadzu Corporation) Capillary column: DB-5, 0.25mm x 30m x 0.25μmφ (Azilen) (Manufactured by T-Technology Co., Ltd.) Detector: FID Detector temperature: 300℃ Inlet temperature: 280℃ Temperature increase 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 volume: 1μL [Gas chromatography measurement conditions 2] Gas chromatograph: GC-2014 (manufactured by Shimadzu Corporation) Packed column: Silicone SE-30 (manufactured by GL Sciences Co., Ltd.) Detector: TCD Detector temperature: 300℃ Inlet temperature: 300℃ Temperature increase program: 70°C (0 min) → 10°C / min → 300°C (10 min) Carrier gas: Helium (50 mL / min) Injection volume: 1μL

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

[0053] [Examples 1-2] To 100 parts by mass of dimethoxymethylsilane, 0.05 parts by mass of formamide was added at room temperature and the mixture was stirred at room temperature for 1 hour. Initially, the formamide dispersed in the dimethoxymethylsilane, and after stirring, the mixture contained dissolved formamide, yielding a homogeneous, colorless, transparent liquid dimethoxymethylsilane composition. Analysis of the obtained dimethoxymethylsilane composition by gas chromatography confirmed that the purity of the dimethoxymethylsilane was 99.65%.

[0054] [Examples 1-3] To 100 parts by mass of dimethoxymethylsilane, 0.1 parts by mass of formamide was added at room temperature and the mixture was stirred at room temperature for 1 hour. Initially, the formamide dispersed in the dimethoxymethylsilane, and after stirring, the mixture contained dissolved formamide, yielding a homogeneous, colorless, transparent liquid dimethoxymethylsilane composition. Analysis of the obtained dimethoxymethylsilane composition by gas chromatography confirmed that the purity of the dimethoxymethylsilane was 99.62%.

[0055] [2] Stability test of the hydrogen silane 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 was thoroughly nitrogen-purged and sealed, and its stability was confirmed at 25°C. The containers were opened at 50, 100, and 150 days, and the dimethoxymethylsilane compositions were 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 Examples 1-2 was placed in a 20 L SUS316 container that had been thoroughly purged with nitrogen and sealed, and its stability was confirmed at 25°C. The containers were opened after 15, 100, and 150 days, and the dimethoxymethylsilane compositions were analyzed by gas chromatography. The results are shown in Tables 1 and 2.

[0057] [Examples 2-3] Fifteen kg of the dimethoxymethylsilane compositions obtained in Examples 1-3 were placed in a 20 L SUS316 container that had been thoroughly nitrogen-purged and sealed, and their stability was confirmed at 25°C. The containers were opened after 15, 100, and 150 days, and the dimethoxymethylsilane compositions were 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 nitrogen-purged and sealed, and its stability was confirmed at 25°C. The samples were opened at 50, 100, and 150 days, and dimethoxymethylsilane was analyzed by gas chromatography. The results are shown in Tables 1 and 2.

[0059] [Table 1]

[0060] [Table 2]

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

[0063] [Table 3]

[0064] [Table 4]

[0065] As shown in Tables 1-4, in Examples 2-1 to 2-4, the dimethoxymethylsilane compositions prepared in Examples 1-1 to 1-3 showed reduced self-reactivity of the hydrogensilane compound due to the interaction between the hydrogensilane compound and the acid amide compound, thus mitigating the decrease in purity of the dimethoxymethylsilane. Furthermore, the low content of trimethoxymethylsilane resulted in a more stable state with reduced chemical changes, and the disproportionation and dehydrogenation reactions proceeded more slowly. Acid amide compounds exhibit tautomerism, transforming into the structure of acid imide compounds through tautomerism. These acid imide compounds contain imide and hydroxyl groups that react with the hydrogen silane compound, and it is thought that the interaction of these substituents reduces the self-reactivity of the hydrogen silane compound.

[0066] On the other hand, in Comparative Examples 2-1 to 2-2, where no acid amide compound was present, the disproportionation and dehydrogenation reactions were accelerated, resulting in a decrease in the purity of dimethoxymethylsilane per unit of elapsed time. In particular, the rate of purity decrease was large when the accelerated test by heating was performed in Comparative Example 2-2. Furthermore, the trimethoxymethylsilane content was also high, and the chemical changes were not mitigated.

[0067] [3] Hydrosilylation reaction using a hydrogen silane composition 1 [Example 3-1] Synthesis of n-octyldimethoxymethylsilane In a flask equipped with a stirrer, reflux apparatus, dropping funnel, and thermometer, 112.2 g (1,000 mol) of 1-octene and a 2-ethylhexanol solution of platinum(IV) chloride (0.00003 mol as platinum atoms) were charged at room temperature, and the raw material solution was heated over 0.5 hours until it reached 70°C. After the internal temperature stabilized, 79.7 g (0.750 mol as dimethoxymethylsilane compound) obtained in Example 1-2 was added dropwise to the raw material solution over 5 hours at 60-80°C, and the mixture was stirred at that temperature for 1 hour. The resulting reaction mixture was a homogeneous, transparent brown liquid. Analysis by gas chromatography revealed the following composition based on the area percentages of the reaction mixture. The results are shown in Table 5.

[0068] [Comparative Example 3-1] Synthesis of n-octyldimethoxymethylsilane The 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 chloroplatin(IV) acid, and then formamide-free dimethoxymethylsilane was added dropwise. The resulting reaction mixture was a heterogeneous brown transparent liquid containing brown solids. Analysis by gas chromatography revealed the following composition based on the area percentages of the reaction mixture. The results are shown in Table 5.

[0069] [Comparative Example 3-2] Synthesis of n-octyldimethoxymethylsilane The reaction was carried out in the same manner as in Example 3-1, except that a formamide-free dimethoxymethylsilane was used instead of the dimethoxymethylsilane composition. The resulting reaction mixture was a homogeneous, transparent brown liquid. Analysis by gas chromatography revealed the following composition based on the area percentages of the reaction mixture. The results are shown in Table 5.

[0070] [Table 5] A1 = Dimethoxymethylsilane B1 = Trimethoxymethylsilane C1 = 1 - Octene D1 = Octene (structural isomer) E1=n-octyldimethoxymethylsilane (adductor isomer) F1 = n-octyldimethoxymethylsilane (target substance)

[0071] [Example 3-2] Synthesis of n-octyltrimethoxysilane To 100 parts by mass of trimethoxysilane, 0.05 parts by mass of formamide was added at room temperature and the mixture was stirred at room temperature for 1 hour. Initially, the formamide dispersed in the trimethoxysilane, and after stirring, the mixture contained dissolved formamide, yielding a homogeneous, colorless, transparent 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 moles as a trimethoxysilane compound) was used instead of the dimethoxymethylsilane composition. The resulting reaction mixture was a homogeneous, transparent brown liquid. Analysis by gas chromatography revealed the following composition based on the area percentages of the reaction mixture. 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 chloroplatin(IV) acid, and then trimethoxysilane without formamide was added dropwise. The resulting reaction mixture was a heterogeneous brown transparent liquid containing brown solids. Analysis by gas chromatography revealed the following compositional ratios of the reaction mixture by area percentage. The results are shown in Table 6.

[0073] [Comparative Example 3-4] Synthesis of n-octyltrimethoxysilane The reaction was carried out in the same manner as in Example 3-2, except that a formamide-free trimethoxysilane was used instead of the trimethoxysilane composition. The resulting reaction mixture was a homogeneous, transparent brown liquid. Analysis by gas chromatography revealed the following composition based on the area percentages of the reaction mixture. The results are shown in Table 6.

[0074] [Table 6] A2 = Trimethoxysilane B2 = Tetramethoxysilane C2 = 1 - octene D2 = Octene (structural isomer) E2=n-octyltrimethoxysilane (adductor isomer) F2 = n-octyltrimethoxysilane (target substance)

[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 at room temperature for 1 hour. Initially, the formamide dispersed in the diethoxymethylsilane, and after stirring, the mixture contained dissolved formamide, yielding 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 moles as a diethoxymethylsilane compound) was used instead of the dimethoxymethylsilane composition. The resulting reaction mixture was a homogeneous, transparent brown liquid. Analysis by gas chromatography revealed the following composition based on the area percentages of the reaction mixture. The results are shown in Table 7.

[0076] [Comparative Example 3-5] Synthesis of n-octyldiethoxymethylsilane The 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 chloroplatin(IV) acid, and then formamide-free diethoxymethylsilane was added dropwise. The resulting reaction mixture was a heterogeneous brown transparent liquid containing brown solids. Analysis by gas chromatography revealed the following composition based on the area percentages of the reaction mixture. The results are shown in Table 7.

[0077] [Comparative Example 3-6] Synthesis of n-octyltrimethoxysilane The reaction was carried out in the same manner as in Example 3-3, except that a formamide-free diethoxymethylsilane was used instead of the diethoxymethylsilane composition. The resulting reaction mixture was a homogeneous, transparent brown liquid. Analysis by gas chromatography revealed the following composition based on the area percentages of the reaction mixture. The results are shown in Table 7.

[0078] [Table 7] A3 = Diethoxymethylsilane B3 = Triethoxymethylsilane C3 = 1 - Octene D3 = Octene (structural isomer) E3=n-octyldiethoxymethylsilane (adductor isomer) F3 = n-octyldiethoxymethylsilane (target substance)

[0079] [Examples 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 at room temperature for 1 hour. Initially, the formamide dispersed in the triethoxysilane, and after stirring, the mixture contained dissolved formamide, yielding a homogeneous, colorless, transparent 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 moles as a triethoxysilane compound) was used instead of the dimethoxymethylsilane composition. The resulting reaction mixture was a homogeneous, transparent brown liquid. Analysis by gas chromatography revealed the following composition based on the area percentages of the reaction mixture. The results are shown in Table 8.

[0080] [Comparative Example 3-7] Synthesis of n-octyltriethoxysilane The reaction was carried out in the same manner as in Examples 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 chloroplatin(IV) acid, and then triethoxysilane without formamide was added dropwise. The resulting reaction mixture was a heterogeneous brown transparent liquid containing brown solids. Analysis by gas chromatography revealed the following compositional ratios of the reaction mixture's area percentages. The results are shown in Table 8.

[0081] [Comparative Example 3-8] Synthesis of n-octyltriethoxysilane The reaction was carried out in the same manner as in Examples 3-4, except that a formamide-free triethoxysilane was used instead of the triethoxysilane composition. The resulting reaction mixture was a homogeneous, transparent brown liquid. Analysis by gas chromatography revealed the following composition based on the area percentages of the reaction mixture. The results are shown in Table 8.

[0082] [Table 8] A4 = Triethoxysilane B4 = Tetraethoxysilane C4 = 1 - Octene D4 = Octene (structural isomer) E4=n-octyltriethoxysilane (adductorative isomer) F4 = n-octyltriethoxysilane (target substance)

[0083] As shown in Tables 5-8, 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 the formation of structural isomers of the less reactive starting compound (D1-D4 in the table) was suppressed, resulting in an improved yield of the target product (F1-F4 in the table).

[0084] On the other hand, in Comparative Examples 3-1, 3-3, 3-5, and 3-7, when the acid amide compound is present in the reaction system before interacting with the hydrogensilane compound, it acts as a catalytic poison for the hydrosilylation reaction catalyst, preventing the reaction from proceeding and resulting in a decrease in the yield of the target product. Furthermore, the brown solid produced during the reaction contained an acid amide compound and a 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, the absence of the acid amide compound reduces the reaction selectivity and rate of the hydrosilylation reaction of the hydrogensilane compound, resulting in a high number of structural isomers and a decrease in the yield of the target product.

[0085] [4] Hydrosilylation reaction using a hydrogen alkoxysilane composition 2 [Example 4-1] Synthesis of 3-Glycidoxypropyldimethoxymethylsilane In a flask equipped with a stirrer, reflux apparatus, dropping funnel, and thermometer, 114.1 g (1,000 mol) of allyl glycidyl ether and a 2-ethylhexanol solution of platinum(IV) chloride (0.00001 mol as platinum atoms) were charged at room temperature, and the raw material solution was heated over 0.5 hours until it reached 70°C. After the internal temperature stabilized, 85.0 g (0.800 mol as dimethoxymethylsilane compound) obtained in Example 1-2 was added dropwise to the raw material solution over 5 hours at 60-80°C, and the mixture was stirred at that temperature for 1 hour. The resulting reaction mixture was a homogeneous, transparent brown liquid. Analysis by gas chromatography revealed the following composition based on the area percentages of the reaction mixture. The results are shown in Table 9.

[0086] [Comparative Example 4-1] Synthesis of 3-Glycidoxypropyldimethoxymethylsilane The reaction was carried out in the same manner as in Example 4-1, except that a formamide-free dimethoxymethylsilane was used instead of the dimethoxymethylsilane composition. The resulting reaction mixture was a homogeneous, transparent brown liquid. Analysis by gas chromatography revealed the following composition based on the area percentages of the reaction mixture. The results are shown in Table 9.

[0087] [Table 9] A5 = Dimethoxymethylsilane B5 = Trimethoxymethylsilane C5 = Allylglycidyl ether D5 = Propenylglycidyl ether E5 = 2-glycidoxy-1-methyl-ethyldimethoxymethylsilane (adductor isomer) F5 = 3-Glycidoxypropyldimethoxymethylsilane (target substance)

[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 at room temperature for 1 hour. Initially, the formamide dispersed in the trimethoxysilane, and after stirring was complete, the mixture contained dissolved formamide, yielding a homogeneous, colorless, transparent 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 moles as a trimethoxysilane compound) was used instead of the dimethoxymethylsilane composition. The resulting reaction mixture was a homogeneous, transparent brown liquid. Analysis by gas chromatography revealed the following composition based on the area percentages of the reaction mixture. The results are shown in Table 10.

[0089] [Comparative Example 4-2] Synthesis of 3-glycidoxypropyltrimethoxysilane The reaction was carried out in the same manner as in Example 4-2, except that a formamide-free trimethoxysilane was used instead of the trimethoxysilane composition. The resulting reaction mixture was a homogeneous, transparent brown liquid. Analysis by gas chromatography revealed the following composition based on the area percentages of the reaction mixture. The results are shown in Table 10.

[0090] [Table 10] A6 = Trimethoxysilane B6 = Tetramethoxysilane C6 = Allyl Glycidyl Ether D6 = Propenylglycidyl ether E6 = 2-glycidoxy-1-methyl-ethyltrimethoxysilane (adductor isomer) F6 = 3-Glycidoxypropyltrimethoxysilane (target substance)

[0091] [Example 4-3] Synthesis of 1-dimethoxymethylsilyl-2-trimethoxysilylethane In a flask equipped with a stirrer, reflux apparatus, dropping funnel, and thermometer, 143.2 g (1,000 mol) of vinyltrimethoxysilane and a 2-ethylhexanol solution of platinum(IV) chloride (0.00001 mol as platinum atoms) were charged at room temperature, and the raw material solution was heated over 0.5 hours until it reached 70°C. After the internal temperature stabilized, 85.0 g (0.800 mol as dimethoxymethylsilane compound) obtained in Example 1-2 was added dropwise to the raw material solution over 5 hours at 60-80°C, and the mixture was stirred at that temperature for 1 hour. The resulting reaction mixture was a homogeneous, transparent brown liquid. Analysis by gas chromatography revealed the following composition based on the area percentages of the reaction mixture. The results are shown in Table 11.

[0092] [Comparative Example 4-3] Synthesis of 1-dimethoxymethylsilyl-2-trimethoxysilylethane The reaction was carried out in the same manner as in Example 4-3, except that a formamide-free dimethoxymethylsilane was used instead of the dimethoxymethylsilane composition. The resulting reaction mixture was a homogeneous, transparent brown liquid. Analysis by gas chromatography revealed the following composition based on the area percentages of the reaction mixture. The results are shown in Table 11.

[0093] [Table 11] A7 = Dimethoxymethylsilane B7 = Trimethoxymethylsilane C7 = Vinyltrimethoxysilane D7 = Ethyltrimethoxysilane E7 = 1-dimethoxymethylsilyl-1-trimethoxysilylethane (adductor isomer) F7 = 1-dimethoxymethylsilyl-2-trimethoxysilylethane (target substance)

[0094] [Example 4-4] Synthesis of N-phenyl-3-aminopropyltrimethoxysilane To 100 parts by mass of trimethoxysilane, 0.05 parts by mass of formamide was added at room temperature and the mixture was stirred at room temperature for 1 hour. Initially, the formamide dispersed in the trimethoxysilane, and after stirring was complete, the mixture contained dissolved formamide, yielding a homogeneous, colorless, transparent trimethoxysilane composition. In a flask equipped with a stirrer, refluxer, dropping funnel, and thermometer, 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) were charged at room temperature, and the starting material solution was heated over 0.5 hours until it reached 70°C. After the internal temperature stabilized, 110.0 g (0.900 mol as trimethoxysilane compound) was added dropwise to the starting material solution over 5 hours at 60-80°C, and the mixture was stirred at that temperature for 1 hour. The resulting reaction mixture was a homogeneous, pale yellow, transparent liquid. Analysis by gas chromatography revealed the following composition based on the area percentages of the reaction mixture. The results are shown in Table 12.

[0095] [Comparative Example 4-4] Synthesis of N-phenyl-3-aminopropyltrimethoxysilane The reaction was carried out in the same manner as in Example 4-4, except that a formamide-free trimethoxysilane was used instead of the trimethoxysilane composition. The resulting reaction mixture was a homogeneous, pale yellow, transparent liquid. Analysis by gas chromatography revealed the following composition based on the area percentages of the reaction mixture. The results are shown in Table 12.

[0096] [Table 12] A8 = Trimethoxysilane B8 = Tetramethoxysilane C8=N-allylaniline D8 = N-propenylaniline E8 = N-phenyl-2-amino-1-methyl-ethyltrimethoxysilane (adductor isomer) F8 = N-phenyl-3-aminopropyltrimethoxysilane (target substance)

[0097] As shown in Tables 9-12, in Examples 4-1 to 4-4, the interaction of the hydrogensilane compound with the acid amide compound improved the reaction selectivity of the hydrosilylation reaction of the hydrogensilane compound, suppressing the formation of addition isomers with different addition positions (E5-E8 in the table), which are byproducts of the hydrosilylation reaction. Furthermore, the suppression of the formation of structural isomers of the less reactive starting compound (D5-D8 in the table) resulted in an improved yield of the target product (F5-F8 in the table).

[0098] On the other hand, in Comparative Examples 4-1 to 4-4, when the acid amide compound is absent, the reaction selectivity of the hydrosilylation reaction of the hydrogensilane compound is low, resulting in a large number of addition isomers and structural isomers, and a decrease in the yield of the target product.

Claims

1. A hydrogensilane composition comprising a mixture of a hydrogensilane compound represented by the following general formula (1) and an acid amide compound (excluding compositions comprising an organic compound having an unsaturated bond containing an average of one or more carbon-carbon double bonds or carbon-carbon triple bonds per molecule). 【Chemistry 1】 (In the formula, R 1 Each of these 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 of these independently represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, and n is an integer from 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). 【Chemistry 2】 (In the formula, R 3 R is an unsubstituted C1-C30 k-valent hydrocarbon group which may contain a hydrogen atom or a heteroatom, 4 k is a hydrogen atom or an unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms, and these 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 any one of claims 1 to 3, wherein the content of the acid amide compound relative to the hydrogen silane compound is 0.0001 to 1% by mass.

5. The hydrogen silane composition according to any one of claims 1 to 4, wherein the content of the silane compound represented by the following general formula (3) is 0.001 to 2% by mass relative to the hydrogen silane compound. 【Transformation 3】 (In the formula, R 1 and R 2 (This has the same meaning as above, and m is an integer between 0 and 4.)

6. A method for producing a hydrosilylated product, comprising mixing a hydrogensilane composition according to any one of claims 1 to 5 with an organic compound having an unsaturated bond, and then hydrosilylating the hydrogensilane compound contained in the hydrogensilane composition with the organic compound having an unsaturated bond in the presence of a catalyst.

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

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