Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/02—Silicon compounds
  • C07F7/08—Compounds having one or more C—Si linkages
  • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
  • C07F7/1804—Compounds having Si-O-C linkages
  • C07F7/1872—Preparation; Treatments not provided for in C07F7/20
  • C07F7/1876—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-C linkages
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
  • C07B61/00—Other general methods
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/02—Silicon compounds
  • C07F7/08—Compounds having one or more C—Si linkages
  • C07F7/0896—Compounds with a Si-H linkage
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/02—Silicon compounds
  • C07F7/08—Compounds having one or more C—Si linkages
  • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/02—Silicon compounds
  • C07F7/08—Compounds having one or more C—Si linkages
  • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
  • C07F7/1804—Compounds having Si-O-C linkages
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/02—Silicon compounds
  • C07F7/08—Compounds having one or more C—Si linkages
  • C07F7/20—Purification, separation

Definitions

• the hydrogen halosilane compound described in Patent Document 1 generates highly corrosive hydrogen halide due to hydrolysis of the halosilyl group.
• Methods for treating this hydrogen halide include, for example, reacting with a basic compound such as amine, urea, or metal alkoxide to form an amine salt, urea salt, or metal salt, but the problem is that these salts are discharged as waste.
• waste reduction has been cited as a major theme in the Sustainable Development Goals (SDGs)
• the hydrogen halosilane compound generates a large amount of hydrogen halide, raising concerns about the burden on the environment.
• the basic compounds are expensive chemicals.
• salts generated by reaction with hydrogen halides need to be removed by methods such as filtration and separation, which complicates the process and reduces productivity.
• hydrogenalkoxysilane compounds have a high degree of self-reactivity because they have a hydrogen atom and an alkoxy group bonded to a silicon atom in the molecule, and are 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, which leads to problems such as an increase in by-products due to these side reactions.
• Methods for improving the reaction selectivity and reaction rate of the hydrosilylation reaction of hydrogenalkoxysilane compounds include the addition of carboxylic acid compounds, ammonium salts, etc.
• methods for mitigating disproportionation reactions and dehydrogenation reactions include the addition of amine compounds, carboxylates, etc.
• the hydroxyl group of the carboxylic acid compound reacts with the hydrogen atom or alkoxy group of the hydrogenalkoxysilane compound.
• the ammonium salt is decomposed by the reaction heat to generate ammonia.
• Amine compounds are catalytic poisons for hydrosilylation catalysts and cannot be used in hydrosilylation reactions, whereas carboxylates are solids with low compatibility with hydrogenalkoxysilane compounds, so the effect of mitigating disproportionation and dehydrogenation reactions is limited to the portion in contact with the solid surface. Furthermore, the above-mentioned additives each exhibit their own effect independently, and they are not capable of simultaneously improving the reaction selectivity and reaction rate and mitigating the disproportionation reaction and dehydrogenation reaction.
• the present invention has been made in consideration of the above circumstances, and aims to provide a method for producing a hydrogensilane composition and a hydrosilylation reactant 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.
• a method for producing a hydrosilylation reactant comprising 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.
• 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 in which purity reduction and chemical changes are alleviated, and disproportionation reactions and dehydrogenation reactions can be alleviated.
• the acid amide compound that has interacted with the hydrogensilane compound can enhance the reactivity of the hydrogensilane compound through interaction with the hydrosilylation reaction catalyst, thereby improving the reaction selectivity and reaction rate.
• 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.
• R 1 's each independently represent 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.
• Specific examples of the halogen atom for R 1 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
• the monovalent hydrocarbon group 1 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; 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; cyclic alkyl groups such as cyclopentyl and cyclohex
• the hydrogen atoms of these monovalent hydrocarbon groups may be substituted with other substituents, and specific examples of the 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 one or more of these may be used in combination.
• the substitution positions of these substituents are not particularly limited, and the number of substituents is also not limited.
• R 1 is preferably 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, and particularly from the viewpoint of easy availability of the precursor 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.
• R 2 's each independently represent 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. Specific examples of such a group include the same substituents as those exemplified for R 1 .
• n is an integer from 0 to 2 (0, 1, or 2), but 0 or 1 is preferred from the viewpoint of reacting with multiple hydroxyl groups on the substrate surface to enhance adhesion, particularly when the hydrosilylation reaction product obtained in the hydrosilylation reaction described below is used as a silane coupling agent or surface treatment agent.
• compound (1) examples 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.
• trimethoxysilane, triethoxysilane, dimethoxymethylsilane, diethoxymethylsilane, dimethoxysilane, and diethoxysilane are preferred from the viewpoint of reacting with multiple hydroxyl groups on the substrate surface to enhance adhesion, particularly when the hydrosilylation reaction product obtained in the hydrosilylation reaction described below is used as a silane coupling agent or surface treatment agent.
• an acid amide compound represented by the following general formula (2) (hereinafter referred to as "compound (2)”) is preferred.
• R3 represents a hydrogen atom or an unsubstituted hydrocarbon group which may contain a heteroatom and has 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, and has a valence of k, where k is 1 or 2.
• the monovalent hydrocarbon group of R 3 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 groups; sec-propyl, sec-butyl, tert-butyl, sec-pentyl, tert-pentyl, sec-hexyl, tert-hexyl, and sec-heptyl groups.
• 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
• Examples of such monovalent hydrocarbon groups include branched alkyl groups such as aryl, 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.
• the divalent hydrocarbon group of R 3 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.
• alkylene group examples 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
• R3 is preferably a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms, or an alkenyl group having 2 to 20 carbon atoms, and from the viewpoint of easy availability of the precursor raw material, 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.
• R 4 's each independently represent 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.
• this monovalent hydrocarbon group include the same substituents as those exemplified for R 3 .
• R4 is preferably a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms, or a linear alkenyl group having 2 to 20 carbon atoms, and from the viewpoint of easy availability of the precursor raw material, 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.
• 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, and cinnamamide. These may be used alone or in combination of two or more.
• acetamide, formamide, N-methylacetamide, N,N-dimethylacetamide, N-methylformamide, malonamide, succinamide, maleamide, fumaramide, benzamide, propionamide, butyramide, palmitamide, stearamide, oleamide, and erucamide are particularly preferred, with formamide and N-methylformamide being particularly preferred from the viewpoint of ease of interaction with the hydrogen silane compound.
• the content of compound (2) in the hydrogen silane 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 is preferably 0.0001 to 1 mass % relative to compound (1), more preferably 0.001 to 0.5 mass %, even more preferably 0.005 to 0.2 mass %, and even more preferably 0.01 to 0.1 mass %.
• the disproportionation reaction or dehydrogenation reaction of compound (1) in the hydrogen silane composition is alleviated, so that the content of the silane compound represented by the following general formula (3) (hereinafter referred to as "compound (3)”) generated by these reactions can be reduced.
• R 1 and R 2 have the same meanings as above.
• m is an integer of 0 to 4 (0, 1, 2, 3 or 4), and is preferably 0, 1, 2 or 3, and more preferably 0, 1 or 2, particularly from the viewpoint of easy availability of precursor materials.
• 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.
• the content of compound (3) in the hydrogen silane composition is an indicator of the progress of the disproportionation reaction or dehydrogenation reaction of compound (1), and from the viewpoint of reducing by-products in the hydrosilylation reaction of compound (1), the content 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 even more preferably 0.02 to 1 mass % relative to compound (1).
• 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, with gas chromatography being preferred among them.
• 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, with gas chromatography being preferred among them.
• the hydrogen silane composition of the present invention can be 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). From the viewpoint of solubility, however, 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.
• the acid amide compound that interacts with the hydrogen silane compound in the hydrogen silane 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.
• 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.
• compound (4) an organic compound having an unsaturated bond
• Compound (4) is preferably a compound containing, on average, one or more carbon-carbon double bonds or carbon-carbon triple bonds per molecule, and can be appropriately selected from known compounds for use. 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, 1-octadecyne, 1-nonadecene, 2-nonadec
• the resulting hydrosilylation reaction product is used as a silane coupling agent or surface treatment agent, from the viewpoint of reacting with the organic groups of the substrate to impart properties such as improved heat resistance, water resistance, weather resistance, and mechanical strength, as well as adhesion, dispersibility, hydrophobicity, and rust resistance, 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.
• the amount of compound (4) used is not particularly limited as long as the hydrosilylation reaction proceeds, but from the viewpoints 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).
• the catalyst can be any known hydrosilylation reaction catalyst without any particular limitations.
• a catalyst selected appropriately from precious metal catalysts such as platinum, ruthenium, rhodium, palladium, iridium, etc.; and base metal catalysts such as iron, cobalt, nickel, etc.
• platinum catalysts are preferred from the viewpoint of high reactivity.
• the platinum catalyst can be appropriately selected from known platinum (Pt) and complex compounds having platinum as the central metal.
• specific examples of such catalysts include alcohol solutions of chloroplatinic acid, such as a solution of chloroplatinic (IV) acid in 2-ethylhexanol; 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 carrier such as alumina, silica, or carbon.
• These catalysts may be used alone or in combination of two or more.
• alcohol solutions of chloroplatinic acid such as a 2-ethylhexanol solution of chloroplatinic (IV) acid and a toluene or xylene solution of a platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex are preferred.
• the amount of platinum catalyst used is not particularly limited as long as it is an amount that exerts a catalytic effect in the hydrosilylation reaction, but from the viewpoints of reactivity and productivity, the amount of platinum metal used is preferably 0.0000001 to 1 mole, more preferably 0.000001 to 0.1 mole, and even more preferably 0.00001 to 0.01 mole per mole of compound (4).
• compound (4) 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). From the viewpoint of reaction selectivity or reaction rate of the hydrosilylation reaction, however, it is preferable to add the hydrogensilane composition to compound (4). In addition, the hydrosilylation reaction catalyst may be added at any time, however, it is preferable to add the hydrosilylation reaction catalyst to compound (4) and then add the hydrogensilane composition.
• 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.
• 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 alone or in combination of two or more.
• hydrocarbon solvents such as pentane, hexane, cyclohexane, heptane, isooctane, benzene, toluene, and xylene
• ether solvents such as diethyl ether, tetrahydrofuran, and
• the purity of the hydrogen silane compound described below is a value measured under the following gas chromatography measurement condition 1
• the purity of the silane compound, which is a hydrosilylation reactant obtained by the hydrosilylation reaction is a value measured under the following gas chromatography measurement condition 2.
• 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 the stirring, the formamide was dispersed in the dimethoxymethylsilane, and after the stirring was completed, the formamide was dissolved in the mixture, and a homogeneous, colorless, transparent liquid dimethoxymethylsilane composition was obtained. The resulting dimethoxymethylsilane composition was analyzed by gas chromatography, and it was found that the purity of dimethoxymethylsilane was 99.65%.
• Examples 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 the stirring, the formamide was dispersed in the dimethoxymethylsilane, and after the stirring was completed, the formamide was dissolved in the mixture, and a homogeneous, colorless, transparent liquid dimethoxymethylsilane composition was obtained. The resulting dimethoxymethylsilane composition was analyzed by gas chromatography, and it was found that the purity of dimethoxymethylsilane was 99.62%.
• 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 at 25° C. was confirmed. The containers were opened after 50 days, 100 days, and 150 days, and the dimethoxymethylsilane composition was analyzed by gas chromatography. The results are shown in Tables 1 and 2.
• 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. The containers were opened after 15 days, 100 days, and 150 days, and the dimethoxymethylsilane composition was analyzed by gas chromatography. The results are shown in Tables 1 and 2.
• 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. The containers were opened after 15 days, 100 days, and 150 days, and the dimethoxymethylsilane composition was analyzed by gas chromatography. The results are shown in Tables 1 and 2.
• Example 2-4 450 g of the dimethoxymethylsilane composition obtained in Example 1-2 was placed in a 500 mL SUS316 container that had been thoroughly substituted 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.
• the self-reactivity of the hydrogensilane compound was reduced due to the interaction between the hydrogensilane compound and the acid amide compound, and the decrease in purity of dimethoxymethylsilane was mitigated.
• the acid amide compound has tautomerism and is converted to an acid imide compound structure by tautomerization.
• This acid imide compound has an imide group and a hydroxyl group that react with the hydrogen silane compound, and it is considered that the self-reactivity of the hydrogen silane compound is reduced by the interaction of these substituents.
• Comparative Examples 2-1 to 2-2 where no acid amide compound was present, the disproportionation reaction and dehydrogenation reaction were promoted, and a decrease in the purity of dimethoxymethylsilane was observed over time.
• the purity decrease rate was large.
• the content of trimethoxymethylsilane was high, and the chemical change was not mitigated.
• Comparative Example 3-2 Synthesis of n-octyldimethoxymethylsilane A reaction was carried out in the same manner as in Example 3-1, except that dimethoxymethylsilane not containing formamide was used instead of the dimethoxymethylsilane composition. The resulting reaction mixture was a homogeneous brown transparent liquid, which was analyzed by gas chromatography to find that the area percentage ratio of the reaction mixture was as follows: The results are shown in Table 5.
• 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 the stirring, the formamide was dispersed in the trimethoxysilane, and after the stirring was completed, the formamide was dissolved in the mixture, and a uniform, colorless, transparent liquid trimethoxysilane composition was obtained.
• a 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 homogeneous brown transparent liquid, which was analyzed by gas chromatography to find that the area percentage ratio of the reaction mixture was as follows: The results are shown in Table 6.
• Comparative Example 3-4 Synthesis of n-octyltrimethoxysilane A reaction was carried out in the same manner as in Example 3-2, except that trimethoxysilane not containing formamide was used instead of the trimethoxysilane composition. The resulting reaction mixture was a homogeneous brown transparent liquid, which was analyzed by gas chromatography to find that the area percentage ratio of the reaction mixture was as follows: The results are shown in Table 6.
• Example 3-3 Synthesis of n-octyldiethoxymethylsilane 0.05 parts by mass of formamide was added to 100 parts by mass of diethoxymethylsilane at room temperature, and the mixture was stirred for 1 hour at room temperature. At the beginning of the stirring, the formamide was dispersed in the diethoxymethylsilane, and after the stirring was completed, the formamide was dissolved in the mixture, and a homogeneous, colorless, transparent liquid diethoxymethylsilane composition was obtained.
• a reaction was carried out in the same manner as in Example 3-1, except that 120.8 g (0.900 mol as the diethoxymethylsilane compound) of the diethoxymethylsilane composition was used instead of the dimethoxymethylsilane composition.
• the resulting reaction mixture was a homogeneous brown transparent liquid, which was analyzed by gas chromatography to find that the area percentage ratio of the reaction mixture was as follows: The results are shown in Table 7.
• 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 the stirring, the formamide was dispersed in the triethoxysilane, and after the stirring was completed, the formamide was dissolved in the mixture, and a uniform, colorless, transparent liquid triethoxysilane composition was obtained.
• a reaction was carried out in the same manner as in Example 3-1, except that 147.9 g (0.900 mol as triethoxysilane compound) of the triethoxysilane composition was used instead of the dimethoxymethylsilane composition. The resulting reaction mixture was a homogeneous brown transparent liquid, which was analyzed by gas chromatography to find that the area percentage ratio of the reaction mixture was as follows: The results are shown in Table 8.
• 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 relative to 100 parts by mass of triethoxysilane) was charged together with 1-octene and a 2-ethylhexanol solution of chloroplatinic (IV) acid, and then triethoxysilane not containing formamide was added dropwise. The resulting reaction mixture was a heterogeneous brown transparent liquid containing a brown solid, and when this was analyzed by gas chromatography, the area percentage ratio of the reaction mixture was the following composition. The results are shown in Table 8.
• Comparative Example 3-8 Synthesis of n-octyltriethoxysilane A reaction was carried out in the same manner as in Example 3-4, except that triethoxysilane not containing formamide was used instead of the triethoxysilane composition. The resulting reaction mixture was a homogeneous brown transparent liquid, which was analyzed by gas chromatography to find that the area percentage ratio of the reaction mixture was as follows: The results are shown in Table 8.
• 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 catalyst poison for the hydrosilylation reaction catalyst, preventing the reaction from proceeding and reducing the yield of the target product. Furthermore, the brown solid generated 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.
• 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)
• Example 4-2 Synthesis of 3-glycidoxypropyltrimethoxysilane 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 the stirring, the formamide was dispersed in the trimethoxysilane, and after the stirring was completed, the formamide was dissolved in the mixture, and a uniform, colorless, transparent liquid trimethoxysilane composition was obtained.
• a 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 homogeneous brown transparent liquid, which was analyzed by gas chromatography to find that the area percentage ratio of the reaction mixture was as follows: The results are shown in Table 10.
• Comparative Example 4-2 Synthesis of 3-glycidoxypropyltrimethoxysilane A 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 brown transparent liquid, which was analyzed by gas chromatography to find that the area percentage ratio of the reaction mixture was as follows: The results are shown in Table 10.
• Example 4-3 Synthesis of 1-dimethoxymethylsilyl-2-trimethoxysilylethane 143.2 g (1.000 mol) of vinyltrimethoxysilane and a 2-ethylhexanol solution of chloroplatinic (IV) acid (0.00001 mol as platinum atom) were charged into a flask equipped with a stirrer, a reflux condenser, a dropping funnel and a thermometer at room temperature, and the raw material solution was heated over 0.5 hours until it reached 70° C.
• chloroplatinic (IV) acid 0.00001 mol as platinum atom
• 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 the stirring, the formamide was dispersed in the trimethoxysilane, and after the stirring was completed, the formamide was dissolved in the mixture, and a uniform, colorless, transparent liquid trimethoxysilane composition was obtained.
• 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 trimethoxysilane not containing formamide was used instead of the trimethoxysilane composition.
• the resulting reaction mixture was a homogeneous, pale yellow, transparent liquid, which was analyzed by gas chromatography to find that the area percentage ratio of the reaction mixture was as follows: The results are shown in Table 12.
• Comparative Examples 4-1 to 4-4 when the acid amide compound is not present, the reaction selectivity of the hydrosilylation reaction of the hydrogen silane compound is low, resulting in a large amount of addition isomers and structural isomers, and a low yield of the target product.

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