JPH10218885A - Production of hydrocarbyloxysilicon compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an efficient production process for a hydrocarbyloxysilicon compound of high quality in high yield. SOLUTION: An alcoholic or phenolic hydroxyl group-bearing compound is allowed to react with a halogenated silicon compound, the product is subjected to dehydrohalogenation, a silylating agent bearing Si-N bond(s) is allowed to react with the product to complete the dehydrohalogenation as well as to silylate the remaining hydroxyl-bearing compound.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a method for producing a compound having a hydrocarbyloxy group bonded to a silicon atom by a dehydrohalogenation reaction between a silicon halide compound and a hydroxyl group-containing organic compound.
After reacting a silicon halide compound with a compound containing an alcoholic or phenolic hydroxyl group and dehydrohalogenating, reacting with a silylating agent having a Si-N bond to complete the dehydrohalogenation With
The present invention relates to a method for producing a hydrocarbyloxysilicon compound such as an alkoxysilane compound or a phenoxysilane compound, which comprises silylating a remaining hydroxyl-containing organic compound.

[0002]

2. Description of the Related Art Methods for hydrocarbyloxylation of silicon halide compounds are widely known. A method using a compound containing a hydroxyl group such as alcohols and phenols is generally used because of easiness of operation and low raw material cost. Since this reaction is an equilibrium reaction, how to remove by-product hydrogen halide to the outside of the reaction system is the rate-determining reaction. In particular, when the target hydrocarbyloxysilicon compound is unstable in an acidic aqueous solution and easily undergoes a hydrolysis reaction or a condensation reaction, the removal of the hydrogen halide is important. In order to improve the efficiency of the removal of hydrogen halide, (1) a method of blowing a large amount of inert gas into the reaction system, and (2) a method of adding a base as a hydrogen halide scavenger in the reaction system. (Japanese Patent Laid-Open No. 52-
No. 116425 and JP-A-53-135935), (3) a method of refluxing with a low boiling point solvent (see JP-A-63-310893), and (4) a method of reducing the pressure in the reaction system. Has been adopted. And
In these methods, an excess of a hydroxyl group-containing compound is generally used to complete the reaction.

[0003] However, particularly when phenolic hydroxyl group-containing compounds are used, they are generally solid at room temperature. Therefore, when the target product is purified by distillation after the reaction, it solidifies in the condenser and clogs the condenser. In addition, phenols adhered to the condenser are eluted during distillation of the target product, and the target product is contaminated.

[0004] Further, when the target compound and the starting compound are separated and purified by liquid chromatography after the reaction, the hydroxyl group-containing compound has a high polarity, and therefore has a high adsorption affinity for the adsorbent (filler), and the eluent and the like. There are problems that it is difficult to select a developing solvent and that the hydroxyl group-containing compound itself is adsorbed and cannot be completely recovered.

[0005]

SUMMARY OF THE INVENTION The present invention has been made to solve the above-mentioned problems of the prior art.
An object of the present invention is to provide a method for producing a hydrocarbyloxysilicon compound efficiently, with high purity, and with high yield. Here, the hydrocarbyloxysilicon compound means a compound having a hydrocarbyloxy group such as a substituted or unsubstituted alkoxy group or a phenoxy group bonded to a silicon atom.

[0006]

Means for Solving the Problems The present inventors have proposed various processes for producing hydrocarbyloxysilicon compounds by a dehydrohalogenation reaction of a silicon halide compound with a compound having an alcoholic or phenolic hydroxyl group. As a result of the examination, it was found that the silylating agent containing a Si—N bond captures the hydrogen halide to complete the dehydrohalogenation reaction, and that the remaining hydroxyl group-containing compound is silylated by the same silylating agent. Investigating, focusing on the fact that the freezing point increases and the polarity decreases, solidification in the condenser during distillation purification is suppressed, and the adsorption affinity in liquid chromatography decreases, improving the separability. As a result, the present invention has been completed.

That is, the method for producing a hydrocarbyloxysilicon compound of the present invention comprises the steps of: adding an alcoholic or phenolic hydroxyl group to a silicon halide compound having a Si—X bond (X represents chlorine, bromine or iodine); Is reacted and dehydrohalogenated, and then reacted with a silylating agent having a Si—N bond to complete the dehydrohalogenation and silylate the remaining hydroxyl-containing compound. It is characterized by the following.

[0008]

BEST MODE FOR CARRYING OUT THE INVENTION As the silicon halide compound used in the present invention, a Si—X bond (where X is
Is not particularly limited as long as it has the above-mentioned), and examples thereof include the following compounds.

(1) General formula: R ¹ _a SiX _4-a (wherein X is as described above; R ¹ may be the same or different and does not contain a hydrogen atom or an aliphatic unsaturated bond) A represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms, preferably 1 to 6 carbon atoms;
Halosilane compound represented by the formula: trimethylchlorosilane, triethylchlorosilane, trimethylbromosilane, triisopropylchlorosilane, tri-n-butylchlorosilane, triphenylchlorosilane, chloromethyldimethylchlorosilane, 3-bromo Triorganohalosilanes such as propyldimethylchlorosilane and 3-mercaptopropyldimethylchlorosilane; diorganodihalosilanes such as dimethyldichlorosilane, diethyldichlorosilane, diphenyldichlorosilane, methylphenyldichlorosilane and dimethyldibromosilane; methyltrichlorosilane and ethyl Trichlorosilane, tert-butyltribromosilane,
Organotrihalosilanes such as chloromethyltrichlorosilane and 3-bromopropyltribromosilane; halosilanes having a Si—H bond in a molecule such as trichlorosilane, methyldichlorosilane and dimethylchlorosilane; and tetrahalosilanes such as tetrachlorosilane and tetraiodosilane Halosilanes.

(2) General formula: R ² _b Y _c SiX _4-bc (wherein X is as described above; R ² is a hydrogen atom or an aliphatic unsaturated bond which may be the same or different. Represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms, preferably 1 to 6 carbon atoms; Y represents a group containing an ethylenically unsaturated group; a represents an integer of 0 to 2; , C
Is an integer of 1 to 3, provided that b + c is an integer of 1 to 3)
An unsaturated halosilane compound represented by the following;
Triorganohalosilanes such as dimethylvinylchlorosilane, allyldimethylchlorosilane, and 5-hexenyldimethylbromosilane; methylvinyldichlorosilane, allylphenyldichlorosilane, (4-ethenylphenyl) methyldichlorosilane, and 3-acryloxypropylmethyldichlorosilane Diorganodihalosilanes such as;
And organotrihalosilanes such as vinyltrichlorosilane, 2- (4-ethenylphenyl) ethyltrichlorosilane, and 3-methacryloxypropyltrichlorosilane.

(3) General formula: R ³ _d X _3-d Si [OR ⁴ Si] _n OSiR ⁵ _d X _3-e (where X is as described above; R ³ , R ⁴ and R ⁵ are
Each represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms, preferably 1 to 6 carbon atoms, which may be the same or different; An integer of 2 and n is an integer of 0 to 2); specific examples thereof include 1,3-dichloro-1,1,3,3-tetramethyldisiloxane, 3-dichloro-1,3-dimethyl-1,3-diphenyldisiloxane, 1,3-dichloro-1,3-dimethyl-1,3-divinyldisiloxane, 1,3-dichloro-1,3-dimethyldisiloxane Siloxane, 1,3-dibromo-1,1,3,3-tetramethyldisiloxane, 1,3-dibromo-1,3-dimethyldisiloxane, 1,1,3-trichloro-1,3,3-trimethyl Disiloxane, 1,1,3,3-tetrachloro-1,3-dimethyldisiloxane, 1,1,3,3-tetrachloro-1,3-diphenyldisiloxane and other organohalodisiloxanes; 1,5-dichloro-1 , 1,
Organohalotrisiloxanes such as 3,3,5,5-hexamethyltrisiloxane; and organohalotrisiloxanes such as 1,7-dichloro-1,1,3,3,5,5,7,7-octamethyltetrasiloxane Tetrasiloxane may be mentioned.

[0012] (4) General ^{_{formula: R 5 f X 3-f}} SiSiR 6 q X 3-g ( wherein, X is as above; R ⁵ and R ⁶ are each, even the same as or different from each other A divalent silane represented by a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 30, preferably 1 to 6 carbon atoms; f and g are each an integer of 0 to 2) Compound; Specific examples are 1,2-dichloro-1,1,2,2
2-tetramethyldisilane, 1,1-dichloro-1,
2,2-trimethyl-2-phenyldisilane, 1,1,
2-trichloro-1,2,2-trimethyldisilane,
1,1,2-trichloro-1,2,2-triphenyldisilane, 1,1,2-tribromo-1,2,2-trimethyldisilane, 1,1,2,2-tetrachloro-1,2
-Dimethyldisilane, 1,1,2,2-tetrachloro-
Examples thereof include 1,2-diphenyldisilane and 1,1,2,2-tetrabromo-1,2-dimethyldisilane.

[0013] (5) the general ^{_{formula: R 7 h X 3-h}} SiQSiR 8 i X 3-i ( wherein, X is as described above; R ⁷ and R ⁸ are, respectively, be the same with or different from each other Q represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 30 carbon atoms, preferably 1 to 6 carbon atoms;
Represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms, preferably 1 to 10 carbon atoms;
A halosylcarban compound represented by the formula:
Specific examples include 1,1-bis (dimethylchlorosilyl) methane, 1,2-bis (diethylbromosilyl) ethane, 1,3-bis (methyldichloro) propane,
4-bis (methyldichlorosilyl) benzene, 1,5-
Bis (trichlorosilyl) hexane, 1,6-bis (trichlorosilyl) hexane, 1,4-bis [2- (trichlorosilyl) ethyl] benzene and the like can be mentioned.

Examples of the compound containing an alcoholic or phenolic hydroxyl group used in the present invention include the following.

That is, as the aliphatic hydroxyl group-containing compound, methyl alcohol, ethyl alcohol, propyl alcohol, isopropyl alcohol, n-butyl alcohol, isobutyl alcohol, sec-butyl alcohol, tert-butyl alcohol, n-pentyl alcohol, isopentyl Alcohol, n-hexyl alcohol, 4-methyl-2-pentanol, n-heptyl alcohol, n-octyl alcohol, 2-ethylhexyl alcohol, n-decyl alcohol, isodecyl alcohol, 1-dodecyl alcohol, 1-tetradecyl alcohol Alcohols having a linear or branched aliphatic saturated hydrocarbon group, such as, 1-hexadecyl alcohol and 1-octadecyl alcohol; cyclohexanol, methylcyclohexanol, Black dodecyl alcohol,
Alicyclic monohydric alcohols such as tetrahydrofurfuryl alcohol and furfuryl alcohol; 2-methoxyethanol, 2-ethoxyethanol, 2-butoxyethanol, 3-methoxy-1-butanol, 3-methyl-3-
Ether alcohols such as methoxy-1-butanol;
Ethylene chlorohydrin, epichlorohydrin, 2-
(2-chloroethoxy) ethanol, 3-chloro-1-
Alcohol having a substituted hydrocarbon group such as propanol; allyl alcohol, 3-methyl-1-butyne-3-
Alcohols having an aliphatic unsaturated hydrocarbon group such as all; and polyhydric alcohols such as ethylene glycol, propylene glycol, 1,4-butanediol, 1,6-hexanediol, glycerin, and trimethylolpropane.

As the aromatic hydroxyl group-containing compound, 2-phenylethyl alcohol, 2-phenoxyethanol,
Aromatic ring-containing alcohols such as 2,2-diphenylethyl alcohol and 2- (α-naphthyl) ethyl alcohol;
And phenol, o-methylphenol, p-methylphenol, xylenol, 2,4,6-trimethylphenol, o-ethylphenol, p-tert-butylphenol, 2,6-di-tert-butylphenol, p
-Octylphenol, 3,5-dimethylphenol,
o-methoxyphenol, o-ethoxyphenol, 4
-(1-methyl-1-phenylethyl) phenol,
2,4-di-tert-butylphenol, 2,6-di-te
rt-butylphenol, o-phenylphenol, p-
Phenylphenol, 4-phenoxyphenol, tribenzylphenol, 2-hydroxydibenzofuran,
monohydric phenols such as α-naphthol and β-naphthol; catechol, resorcin, hydroquinone, 4,4 ′
-Polyhydric phenols such as methylene diphenol.

Among these hydroxyl group-containing compounds, from the effect of preventing the adhesion of the hydroxyl group-containing compound in the purification step, which is a feature of the present invention, a hydroxyl group-containing organic compound which is solid at room temperature, such as phenols or higher alcohols. It is particularly effective to apply the production method of the present invention to hydrocarbyloxylation of a silicon halide compound, but the present invention is not limited to this, and the present invention can be used to improve the yield of hydrocarbyloxysilicon compounds in general.

The silylating agent having a Si--N bond used in the present invention converts the hydroxyl group of the hydroxyl group-containing compound remaining in the system into a triorgano or diorganosilylation compound, and at the same time, reacts the basic compound into the system by the silylation reaction. Generates by-products. As such a silylating agent, specifically,
N, O-bis (trimethylsilyl) carbamate, N,
N-dimethylaminotrimethylsilane, N, N-diethylaminotrimethylsilane, hexamethyldisilazane,
Hexaethyldisilazane, tetramethyldisilazane, N
-Trimethylsilyl imidazole and the like. Of these, hexamethyldisilazane is most preferred because it is easy to obtain and handle and it is easy to remove by-product ammonia.

The method for producing a hydrocarbyloxysilicon compound of the present invention is typically carried out as follows. That is, first, a compound containing an alcoholic or phenolic hydroxyl group is melted by heating to a temperature equal to or higher than the melting point, and 0.8 mol / mol of the hydroxyl group-containing compound is added.
An amount of the silicon halide compound that gives ~ 1.2 mol of reactive halogen atoms is added dropwise. Here, the heating temperature is preferably a temperature at which the hydroxyl group-containing compound is melted and the silicon halide compound to be dropped is not easily distilled off. The heating temperature varies depending on the type of the two compounds used, but usually 30 to 200. ° C, preferably 50 to 150 ° C.

After the dropwise addition of the silicon halide compound, it is preferable to continue heating to promote the dehydrohalogenation reaction. In order to promote the distillation of hydrogen halide in this step, degassing is performed by blowing an inert gas into the reaction system or reducing the pressure to such an extent that the silicon halide compound does not distill. Hydrogen halide may be performed. In order to further reduce the amount of the silylating agent containing a Si—N bond in the next step, the remaining amount of the hydrogen halide in the system is 0 to 10,
The heating is preferably continued until the concentration reaches 000 ppm, more preferably 0 to 2,000 ppm.

Next, the temperature is usually 30 to 200 ° C., preferably 5 to 200 ° C.
At 0 to 150 ° C., an amount of S that gives 1.0 to 5.0 mol, preferably 1.0 to 2.0 mol of silyl groups is usually added per 1 mol of hydroxyl groups of the remaining hydroxyl group-containing compound.
A silylating agent containing an iN bond is added to capture the hydrogen halide to complete the dehydrohalogenation reaction and silylate the hydroxyl group of the remaining hydroxyl group-containing compound.

In this step, in order to complete the dehydrohalogenation reaction, another base may be added for the purpose of capturing the hydrogen halide. Such bases include, for example, triethylamine, diisopropylamine, tri-n-octylamine, allylamine, triallylamine, ethylenediamine, tetramethylethylenediamine, triethylenediamine, pyridine, α-picoline, 2,4,6-trimethylpyridine,
Piperidine, 2-methylpiperidine, piperazine, pyrazine, pyrrolidine, 1,8-diazabicyclo [5,4,
0] undec-7-ene and the like.

Further, in the method for producing a hydrocarbyloxysilicon compound of the present invention, a solvent may be used as necessary throughout all the steps, or during the dehydrohalogenation reaction or the filtration. Such a solvent is not particularly limited as long as it is a solvent inert to the raw materials and products. For example, aliphatic hydrocarbons such as pentane, hexane, heptane, octane, isooctane, decane and dodecane; benzene, Aromatic hydrocarbons such as toluene, xylene, ethylbenzene, and naphtha; halogenated hydrocarbons such as trifluoroethylene, perfluoroethylene, and carbon tetrachloride; ethers and polyethers such as dimethyl ether, diethyl ether, dibutyl ether, diethylene glycol dimethyl ether, and tetrahydrofuran And these may be used alone or in combination of two or more.

The hydrochloride is usually precipitated from the reaction mixture containing the hydrocarbyloxysilicon compound as the target substance and the silylated product of the above-mentioned hydroxyl group-containing compound. After being filtered off, purification can be performed by distillation and / or liquid chromatography.

[0025]

According to the method for producing a hydrocarbyloxysilicon compound of the present invention, the hydrogen halide is captured to complete the dehydrohalogenation reaction, and the remaining hydroxyl group-containing compound is silylated to increase the freezing point. Polarity loss occurs. Therefore, it can be suppressed by solidification in a condenser during distillation purification and the separation affinity can be improved by lowering the affinity of adsorption by liquid chromatography, so that a highly pure hydrocarbyloxysilicon compound can be produced in good yield. It has a special effect that it can be done. Furthermore, since the hydrocarbyloxysilicon compound as the target substance can be obtained in a high yield, the operation of the production process is very simple and can be performed efficiently, the production cost can be reduced, and low-cost raw materials can be used. There is also the advantage that it can be used.

The hydrocarbyloxysilicon compound produced by the present invention is used as an intermediate material for various silicones and polysilanes, as well as a crosslinking agent, a silane coupling agent, a modifier for various resins, and a surface treatment agent for various substrates. It is useful as such.

[0027]

The present invention will be described in more detail with reference to the following Examples and Comparative Examples. Parts and% in these examples indicate parts by weight and% by weight. The present invention is not limited by these examples.

Example 1 A flask equipped with a dropping funnel, a stirrer and a Dimroth condenser through which a refrigerant at -20 ° C. circulates was charged in advance with 5 mL.
Charge 100 parts of phenol melted by heating to 0 ° C.
Heat to 60 ° C and stir with methyltrichlorosilane 5
3 parts (molar ratio of phenol / methyltrichlorosilane =
1/3) was added dropwise over 5 hours. And furthermore, 6
Heating and stirring were performed at 0 ° C. for 2 hours. The contents of the flask at this stage are referred to as reaction mixture A.

Then, the temperature of the flask was raised to 100 ° C.
While passing nitrogen gas through the reaction mixture A, heat and stir for 1
Performed for 2 hours. At this stage, the contents of the flask are
Let it be reaction mixture B.

Subsequently, the flask was cooled to 60 ° C., 5 parts of hexamethyldisilazane was added, and the mixture was stirred for 1 hour. The contents of the flask obtained at this stage are referred to as reaction mixture C.

Remove the dropping funnel from the flask,
After attaching the Liebig condenser, adapter for decompression and eggplant-shaped flask, 100 ℃ under reduced pressure of 10 Torr
The temperature was raised to an excessive level, excess hexamethyldisilazane and trimethylphenoxysilane by-produced were distilled off, and the mixture was cooled to room temperature. Then, the hydrochloride produced as a by-product was filtered off to obtain 108 parts of a residue. The residue was analyzed by gas chromatography (GC). As a result, the target methyltriphenoxysilane was contained at a purity of 97.6%. Further, the content of hydrochloric acid by titration using potassium salt of tetrabromophenolphthalein ethyl ester as an indicator with a KOH alcohol solution was 0 ppm.

The residue was purified by distillation under reduced pressure to obtain 98 parts of a purified product of methyltriphenoxysilane having a boiling point of 172 to 176 ° C./2 Torr. The yield based on the theoretical amount was 85.7%. As a result of analyzing the methyltriphenoxysilane thus obtained, the GC purity was 99.6.
% And the hydrochloric acid content was 0 ppm. In addition, the reaction mixtures A to C, the residue of atmospheric distillation and the purified product of distillation,
Table 1 shows the results of the GC analysis and the measurement of the hydrochloric acid content.

Comparative Example 1 A reaction mixture B 'corresponding to the reaction mixture B was prepared by the same raw material composition and operation as in Example 1. This was subjected to distillation purification using a T-shaped tube, a Liebig condenser, a three-pronged adapter and a pear-shaped flask equipped with an eggplant-shaped flask to obtain 87.3 parts of a distilled purified product having a boiling point of 172 to 176 ° C / 2 Torr. . The yield relative to the theoretical amount is
76.3%. GC purity of methyltriphenoxysilane in the obtained distilled purified product was 91.2%, the content of hydrochloric acid was 700 ppm, and the product had a strong hydrochloric acid odor. During distillation purification, phenol was coagulated and fixed in the Liebig condenser to block the distillation system, so that it was often necessary to dissolve the fixed substance using a drier or the like. Table 1 shows the results of GC analysis and hydrochloric acid measurement of the obtained reaction mixture B 'and the purified purified product.

[0034]

[Table 1]

Example 2 A flask equipped with a dropping funnel, a stirrer and a Dimroth condenser in which a -20 ° C. refrigerant circulates was previously charged with
1-octadecyl alcohol 2 melted by heating to 0 ° C
88 parts were charged and heated at 70 ° C. while stirring and 53 parts of methyltrichlorosilane (1-octadecyl alcohol /
(The molar ratio of methyltrichlorosilane = 1/3) was added dropwise over 5 hours. Then, the mixture was further heated and stirred at 70 ° C. for 2 hours. At this stage, the contents of the flask are
Let it be reaction mixture D.

Then, the temperature of the flask was raised to 100 ° C.
While passing nitrogen gas through the reaction mixture D, the mixture was heated and stirred for 12 hours.
Time went. The contents of the flask at this stage are referred to as reaction mixture E.

Subsequently, the flask was cooled to 60 ° C., 5 parts of hexamethyldisilazane was added, and the mixture was stirred for 1 hour. The contents of the flask obtained at this stage are referred to as reaction mixture F.

Remove the dropping funnel from the flask,
After attaching a Liebig condenser, an adapter for decompression and an eggplant-shaped flask, the temperature was raised to 80 ° C. under a reduced pressure of 10 Torr to distill off excess hexamethyldisilazane and cooled to room temperature. Then, the hydrochloride produced as a by-product was filtered off to obtain 315 parts of a residue. The residue was analyzed by GC.
-Octadecyloxysilane was contained in a purity of 93.4%. The content of hydrochloric acid by titration in the same manner as in Example 1 was 0 ppm.

315 parts of this residue was mixed with a 20-fold amount of silica gel (Wakogel C-30, manufactured by Wako Pure Chemical Industries, Ltd.).
Purification by liquid chromatography was carried out using 0) as a filler and a mixed solvent of hexane / diethyl ether at a volume ratio of 1/1 as a developing solvent. -248 parts of purified octadecyloxysilane were obtained. The yield based on the theoretical amount is 8
3.7%. Methyl tri-1- thus obtained
As a result of analyzing octadecyloxysilane, the GC purity was 99.1% and the hydrochloric acid content was 0 ppm. Table 2 shows the results of GC analysis and measurement of hydrochloric acid content of the reaction mixtures DF, the residues, and the chromatographically purified product.
Shown in

Comparative Example 2 A reaction mixture E 'corresponding to the reaction mixture E was prepared by the same raw material composition and operation as in Example 2. Then, the entire amount of the reaction mixture E 'was mixed with a 20-fold amount of silica gel (Wakogel C-300, manufactured by Wako Pure Chemical Industries, Ltd.) as a filler, and a mixed solvent similar to that used in Example 2 was used. As a developing solvent, purification by liquid chromatography was performed, and a fraction containing the target methyltri-1-octadecyloxysilane was recovered.
231 parts of a purified product were obtained. The yield based on the theoretical amount is 78.
1%. As a result of analyzing the thus obtained methyltri-1-octadecyloxysilane, the GC purity was 9%.
0.1%, and the hydrochloric acid content was 84 ppm. Table 2 shows the results of GC analysis and measurement of hydrochloric acid content of the obtained reaction mixture E 'and the purified purified product.

[0041]

[Table 2]

Claims (4)

[Claims] 1. A halogenated silicon compound having an Si—X bond (wherein X represents chlorine, bromine or iodine) is reacted with a compound containing an alcoholic or phenolic hydroxyl group to dehalogenate the compound. After hydrogenation, S
A method for producing a hydrocarbyloxysilicon compound, which comprises reacting a silylating agent having an iN bond to complete dehydrohalogenation and silylating the remaining hydroxyl group-containing compound. 2. The method according to claim 1, wherein the hydroxyl group-containing compound is a phenol. 3. The method according to claim 1, wherein the silylating agent having a Si—N bond is hexamethyldisilazane. 4. The method of claim 1, wherein the hydrocarbyloxysilicon compound is
The production method according to claim 1, wherein the production method is an alkoxysilane or a phenoxysilane.