A method for preparing a hydrosilylation catalyst

Abstract

The application provides a preparation method of a hydrosilylation catalyst. The preparation method of the hydrosilylation catalyst comprises the following steps: 1) mixing and dispersing an aqueous solution of a water-soluble thickening agent with a non-polar organic solvent to obtain a suspension; 2) adding an alkoxysilanol solution to the suspension obtained in step 1) to perform a hydrolysis reaction, and after the reaction is completed, an organic phase is taken, and after water is removed, a mixture is obtained; 3) adding an alcohol solution of chloroplatinic acid to the mixture obtained in step 2) to perform a coordination reaction, and after the reaction is completed, a precipitate is taken and dried, and the hydrosilylation catalyst is obtained. The catalyst obtained by the preparation method has good storage stability and high reaction efficiency compared with a traditional catalyst, the preparation method is simple, and the catalyst provided by the application does not lose activity under long-term room temperature storage.

Description

Technical Field

[0001] This invention relates to the field of synthesis technology of organosilicon monomers and polymers, and more specifically, to a method for preparing a hydrosilylation reaction catalyst. Background Technology

[0002] Hydrosilylation reactions are addition reactions catalyzed by noble metal catalysts (such as platinum, rhodium, palladium, and iridium compounds) between compounds containing unsaturated bonds (including double and triple bonds, aldehydes, and ketones) and organosilicon compounds containing silicon-hydrogen bonds. This reaction can generate new silicon-carbon and silicon-oxygen bonds and is an important class of reactions for the synthesis of organosilicon monomers and organosilicon polymers. While this reaction has high atom utilization, the high cost and difficulty in recycling of catalysts increase production costs and exacerbate the consumption of precious metal resources.

[0003] Currently, there are several main methods for preparing heterogeneous hydrosilylation catalysts: one method involves reacting a functional organic ligand with a specific structure and surface-hydroxylated silica to obtain a silica-supported organic ligand, which is then reacted with a platinum-containing compound. Another method involves treating silica powder or inorganic supports such as silica-containing molecular sieves with a coupling agent such as chloropropyl alkylsilane, then modifying the surface of such supports with functional compounds such as vinylpyridine or divinylpyridine, and finally coordinating the modified supports with chloroplatinic acid to obtain a supported platinum catalyst with a specific structure. However, the heterogeneous hydrosilylation catalysts obtained by existing technologies cannot simultaneously achieve good storage stability and high reactivity, and some methods are too complex to be suitable for practical industrial production. Summary of the Invention

[0004] To address, or at least partially address, the problems in the prior art, this invention provides a method for preparing a hydrosilylation reaction catalyst. The catalyst obtained by this method exhibits better storage stability and higher reactivity compared to traditional catalysts. Furthermore, the product catalyzed using this catalyst does not exhibit yellowing (or yellowing is significantly reduced). The preparation method provided by this invention is simple, and the catalyst obtained by this invention maintains essentially the same catalytic activity or shows minimal change after long-term storage at room temperature.

[0005] The present invention provides a method for preparing a hydrosilylation reaction catalyst, comprising the following steps:

[0006] 1) Mix and disperse an aqueous solution of a water-soluble thickener with a non-polar organic solvent to obtain a suspension;

[0007] 2) Add alkoxysilanol solution to the suspension obtained in step 1) to carry out hydrolysis reaction. After the reaction is completed, take the organic phase, remove water and obtain a mixture (i.e., the carrier);

[0008] 3) Add chloroplatinic acid alcohol solution to the mixture obtained in step 2) to carry out a coordination reaction. After the reaction is completed, take the precipitate, dry it, and you will get the product.

[0009] The preparation method provided by this invention uses a water-soluble thickener as an additive, in a specific manner provided by this invention, to synthesize a porous silica support through the hydrolysis reaction of alkoxysilanes. This support is then used to immobilize platinum to prepare a heterogeneous catalyst suitable for hydrosilylation reactions. The heterogeneous catalyst prepared by this invention exhibits high catalytic activity, and the catalyzed product does not yellow and can be reused multiple times.

[0010] In a preferred embodiment of the present invention, in step 1), the water-soluble thickener is carboxymethyl cellulose, polyvinyl alcohol, sodium polyacrylate, or polyacrylamide. Water-soluble thickeners have different dissolution and dispersion characteristics in water. Carboxymethyl cellulose forms a spherical colloid in aqueous solution, while polyvinyl alcohol, sodium polyacrylate, polyacrylamide, and other water-soluble thickeners form hydrogels. By selecting different types of thickeners, carriers with different structures can be obtained. Although the structures of the carriers obtained by using different water-soluble thickeners are different, they can all achieve the purpose of the present invention. In a preferred embodiment of the present invention, to further improve the stability and reactivity of the obtained carrier, the water-soluble thickener is preferably carboxymethyl cellulose. The present invention unexpectedly discovered that when carboxymethyl cellulose is used as a water-soluble thickener, the main structure of the obtained catalyst is a hollow spherical shape, and the catalytic activity of the obtained catalyst is also higher.

[0011] In a preferred embodiment of the present invention, the concentration of the aqueous solution of the water-soluble thickener can be 9*10. -5 %~2*10 -3 %. In the present invention, if the concentration of the water-soluble thickener aqueous solution is too high, the silane will not be easily dispersed in the system and will easily polymerize and clump due to hydrolysis; while if the concentration of the thickener aqueous solution is too low, the catalytic effect of the catalyst will be poor.

[0012] In a preferred embodiment of the present invention, in step 1), the non-polar organic solvent is an organic solvent that can form an azeotrope with water, and can be one or more of cyclohexane, n-octane, isooctane, and toluene, more preferably cyclohexane. The amount of the non-polar organic solvent used is 10-50% of the volume of the water-soluble thickener solution in step 1). In the present invention, the boiling point of the azeotrope formed by the non-polar solvent and water affects the catalytic activity of the synthesized catalyst. If the azeotropic temperature is too high, the hydrolysis aging temperature is high, the siloxane condensation is rapid, and the catalytic activity of the obtained catalyst is reduced. If the azeotropic temperature is too low, the aging condensation is incomplete, and the catalytic activity of the obtained catalyst is also low.

[0013] In a preferred embodiment of the present invention, in step 2), the alkoxysilane in the alkoxysilane alcohol solution is one or more of vinyltrimethoxysilane, vinyltriethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, propyltrimethoxysilane, propyltriethoxysilane, tetramethoxysilane, tetraethoxysilane, long-chain alkyl trimethoxysilane, and long-chain alkyl triethoxysilane (wherein the long-chain alkyl group has 6 to 18 carbon atoms); preferably, vinyltrimethoxysilane is mixed with one or more of vinyltriethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, propyltrimethoxysilane, propyltriethoxysilane, tetramethoxysilane, long-chain alkyl trimethoxysilane, and long-chain alkyl triethoxysilane (wherein the long-chain alkyl group has 6 to 18 carbon atoms). To further improve the stability and reactivity of the obtained catalyst, the alkoxysilane is preferably a mixture of vinyltrimethoxysilane and tetramethoxysilane. More preferably, the mass ratio of vinyltrimethoxysilane to tetramethoxysilane in this mixture is (1-10):1, and even more preferably (2-5):1. Through numerous parallel experiments, this invention has found that both excessively large and small ratios will weaken the catalytic activity of the obtained catalyst, and simultaneously reduce its stability and activity after multiple cycles.

[0014] In one specific embodiment of the present invention, in step 2), the alcohol in the alkoxysilane alcohol solution can be methanol, ethanol, isopropanol, ethylene glycol, etc. The proportion of alkoxysilane in the alkoxysilane alcohol solution is 10-50%.

[0015] In a preferred embodiment of the present invention, in step 2), the amount of the aqueous solution of the thickener is 2 to 5.5 times the mass of the alkoxysilanol solution. In a preferred embodiment of the present invention, in step 2), the hydrolysis reaction is carried out at a temperature of 40 to 45°C for 1.5 to 2 hours.

[0016] In a preferred embodiment of the present invention, in order to avoid damaging the structure of the support in the catalyst and further protect the performance of the catalyst, the dehydration step in step 2) is carried out by solvent reflux.

[0017] In a preferred embodiment of the present invention, in step 3), the amount of chloroplatinic acid in the chloroplatinic acid alcohol solution is 0.01% to 0.2% of the mass of the carrier (i.e., the mixture obtained in step 2). The alcohol in the chloroplatinic acid alcohol solution is typically isopropanol.

[0018] In a specific embodiment of the present invention, in step 3), drying can be a drying method commonly used in the art, such as vacuum drying.

[0019] Another object of the present invention is to provide a hydrosilylation reaction catalyst obtained by the above preparation method.

[0020] The catalyst obtained in this invention was applied to the synthesis of long-chain alkyl coupling agents and polyether-modified silane coupling agents, respectively. The rapid temperature rise and surge observed in homogeneous catalytic reactions were avoided, and the reaction process remained stable. The catalyst can be recovered by filtration and can be recycled for further reactions. The resulting product exhibits almost no yellowing, significantly reducing the impact of catalyst residue on product quality and simplifying the production process.

[0021] Another object of the present invention is to provide the application of the above-described preparation method or the hydrosilylation reaction catalyst obtained by the above-described preparation method in the catalytic addition reaction of hydrogen-containing silanes with olefins.

[0022] The hydrogen-containing silanes may include, but are not limited to, trimethoxysilane, triethoxysilane, trichlorosilane, methyldichlorosilane, dimethoxymethylsilane, and diethoxymethylsilane, etc., and the olefins may include, but are not limited to, 1-hexadecene, allyl polyether, 1-hexene, 1-octene, 1-decene, 1-dodecene, 1-octadecene, allyl glycidyl ether, and 4-vinylepoxycyclohexane, etc. In specific embodiments of the present invention, the catalytic activity of the catalyst is verified by the addition reaction of 1-hexadecene with trimethoxysilane and the addition reaction of allyl polyethylene glycol monomethyl ether (detailed using Zhejiang Huangma HMS-274M as an example) with trimethoxysilane. However, this does not mean that the catalyst provided by the present invention only has good activity in these two catalytic reactions. The present invention has confirmed through numerous experiments that the obtained catalyst has good activity in all of the above-mentioned addition reactions of hydrogen-containing silanes and olefins.

[0023] Compared with the prior art, the beneficial effects of the present invention are as follows:

[0024] (1) This invention uses common thickeners as additives. By self-assembling alkoxysilanes in an aqueous solution of the thickener, and adjusting the proportion of different types of alkoxysilanes, structural modifications are made to obtain heterogeneous catalysts with different structural strengths, appearances, and supported / embedded types. This method can control the structure and size of the support and has a wide range of applications.

[0025] (2) The thickener aqueous solution prepared in the process of this invention can be recycled by distillation to remove alcohol after the reaction, thereby reducing the generation of wastewater. In addition to playing the role of emulsifying with the thickener aqueous solution to form a template in the hydrolysis process, the organic solvent can also be used as an azeotropic solvent to remove water in the synthesis process. Moreover, it can be recycled in this preparation method, and no waste solvent is generated.

[0026] (3) The catalyst synthesized by the method provided in this invention is a heterogeneous catalyst with a silica support. It has a very high specific surface area and a high loading rate of noble metals. It also has a steric structure that can improve the selectivity of hydrosilylation reaction.

[0027] (4) The heterogeneous catalyst prepared in this invention can significantly reduce platinum residue and yellowing of polyether adducts in the synthesis of long-chain alkyl coupling agents and polyether-modified silane coupling agents, simplifying the production process and reducing production costs. Furthermore, the catalyst prepared in this invention exhibits higher stability than the Speier and Karstedt catalysts, which are prone to precipitating platinum black after prolonged storage at room temperature. The catalyst provided by this invention does not deactivate after long-term storage at room temperature; that is, its color does not change after long-term storage at room temperature, and its catalytic activity remains high. Moreover, the catalyst provided by this invention can be reused multiple times (at least twice, preferably at least three times, and more preferably at least four times) without significant reduction in catalytic activity. Attached Figure Description

[0028] Figure 1 This is an electron microscope image of the silicon-oxygen addition reaction catalyst obtained in Example 1.

[0029] Figure 2 This is an electron microscope image of the silicon-oxygen addition reaction catalyst obtained in Example 2.

[0030] Figure 3 This is an electron microscope image of the silicon-oxygen addition reaction catalyst obtained in Example 3. Detailed Implementation

[0031] The specific embodiments of the present invention will be described in further detail below with reference to the examples. These examples are used to illustrate the present invention, but are not intended to limit the scope of the invention.

[0032] Example 1

[0033] (1) Dissolve 0.1g of carboxymethyl cellulose in 1000g of deionized water, heat and stir to disperse evenly until no obvious particles are visible, then cool to room temperature, filter to obtain a thickener solution, and add 200ml of cyclohexane to it and stir thoroughly to obtain a suspension. Mix 100g of a mixture of vinyltrimethoxysilane and tetramethoxysilane in a mass ratio of 3:1 with 100g of methanol to obtain a homogeneous alkoxysilanol solution, and place it in a dropping funnel. Turn on the heater to raise the temperature of the suspension to 40℃, and then add the alkoxysilanol solution dropwise. After the addition is completed, continue stirring at 40℃ for 2 hours to obtain a suspension. Let it stand for several hours, cool down and separate the layers. Take the lower aqueous solution, filter the lower aqueous solution to separate the filter cake, and wash the filter cake with a small amount of deionized water. Mix the obtained filter cake with the upper cyclohexane obtained from the separation and stir evenly. Heat the mixture and pass it through the azeotropic reaction of cyclohexane and water until no water droplets condense in the cyclohexane reflux in the water separator to obtain the carrier.

[0034] (2) Add isopropanol chloroplatinic acid solution to the support obtained in step (1) (the isopropanol chloroplatinic acid solution is prepared by dissolving 1g of chloroplatinic acid hexahydrate in 18ml of isopropanol, wherein the amount of isopropanol chloroplatinic acid solution used in this step is such that chloroplatinic acid accounts for 0.2% of the weight of the support), heat to 100℃ and stir for 2h, filter and separate the precipitate, and vacuum dry at -0.1Mpa and 40℃ for 6h to obtain the heterogeneous catalyst (i.e. the hydrosilylation reaction catalyst obtained in this example).

[0035] The electron micrograph of the heterogeneous catalyst obtained in this embodiment is as follows: Figure 1 As shown, the spherical structure is approximately 3-7 μm in size, which is larger than the pore size of the organic filter membrane (2.5 μm). It contains a large number of fragmented structures. The microsphere structure and fragmented structures prove that the catalyst obtained is a hollow structure, which also proves that the method provided in this embodiment can prepare a hollow structure supported catalyst.

[0036] Example 2

[0037] (1) Dissolve 0.1g of sodium polyacrylate in 1000g of deionized water, heat and stir to disperse evenly until no obvious particles are visible, then cool to room temperature, filter to obtain a thickener solution, and add 200ml of toluene to it and stir thoroughly to obtain a suspension. Mix 100g of a 2:1 mixture of vinyltrimethoxysilane and tetramethoxysilane with 300g of methanol to obtain a homogeneous alkoxysilanol solution, and place it in a dropping funnel. Turn on the heater to raise the temperature of the suspension to 40℃, and then add the alkoxysilanol solution dropwise. After the addition is complete, stir at 40℃ for 2h to obtain a suspension. Let stand for several hours to cool down and separate the liquids. The lower aqueous solution is filtered to separate the filter cake, which is then washed with a small amount of deionized water. The filter cake is then removed and mixed with the upper toluene layer and stirred into a slurry. The mixture is then transferred to a flask and heated until the toluene is refluxed. An azeotrope is formed between the toluene and water, and the water carried by the azeotrope is separated by a water separator. The refluxed toluene is cooled until no water droplets condense, thus obtaining the carrier.

[0038] (2) Add isopropanol chloroplatinic acid solution to the support obtained in step (1) (the isopropanol chloroplatinic acid solution is prepared by dissolving 1g of chloroplatinic acid hexahydrate in 18ml of isopropanol, wherein the amount of isopropanol chloroplatinic acid solution used in this step is such that chloroplatinic acid accounts for 0.1% of the weight of the support), heat to 100℃ and stir for 2h, then filter to separate the precipitate, and vacuum dry at -0.1Mpa and 40℃ to obtain the heterogeneous catalyst (i.e. the hydrosilylation reaction catalyst of the present invention).

[0039] The electron micrograph of the heterogeneous catalyst obtained in this embodiment is as follows: Figure 2 As shown, most of them are loose flakes, and no spherical structures were observed.

[0040] Example 3

[0041] (1) Dissolve 2g of polyvinyl alcohol in 1000g of deionized water, heat and stir to disperse evenly, then cool to room temperature, filter to obtain a thickener solution, and add 200ml of n-hexane to it and stir to disperse thoroughly to obtain a suspension. Mix 100g of a mixture of vinyltrimethoxysilane and tetramethoxysilane in a mass ratio of 2:1 with 150g of methanol to obtain an alkoxysilane alcohol solution, and place it in a dropping funnel. Turn on the heater to raise the solution to 40℃ and add it dropwise. After the addition is completed, stir at 40℃ for 2h to obtain a suspension. Let it stand for several hours, cool it down and separate the liquids. Filter the lower aqueous solution to separate the filter cake and wash it with a small amount of deionized water. Take out the filter cake, mix it with the upper n-hexane, stir it into a slurry and transfer it to a flask. Heat the n-hexane to reflux, and separate the water carried by the azeotrope formed by n-hexane and water through a water separator until no water droplets condense in the refluxed n-hexane in the water separator, to obtain the carrier.

[0042] (2) Add isopropanol chloroplatinic acid solution to the support obtained in step (1) (the isopropanol chloroplatinic acid solution is prepared by dissolving 1g of chloroplatinic acid hexahydrate in 18ml of isopropanol, wherein the amount of isopropanol chloroplatinic acid solution used in this step is such that chloroplatinic acid accounts for 0.05% of the weight of the support), heat to 100℃ and stir for 2h, then filter to separate the precipitate, and vacuum dry at -0.1Mpa and 40℃ to obtain the heterogeneous catalyst (i.e. the hydrosilylation reaction catalyst of the present invention).

[0043] The electron micrograph of the heterogeneous catalyst obtained in this embodiment is as follows: Figure 3 As shown, the obtained catalyst has an irregular aggregate structure, with no obvious spherical or plate-like structures.

[0044] Example

[0045] The catalysts prepared in Examples 1-3 were used to catalyze the hydrosilylation reaction of 1-hexadecene, allyl polyether and trimethoxysilane, respectively, and the reaction effects of homogeneous Speier catalyst and Karstedt catalyst were compared.

[0046] 1. The catalysts obtained in Examples 1-3 catalyze the addition of 1-hexadecene to trimethoxysilane:

[0047] 0.1 mol of 1-hexadecene was mixed with 10 ppm (based on Pt) of catalyst (Examples 1-3, Speier catalyst, Karstedt catalyst). After activation at 80°C for 30 min under nitrogen protection, 0.11 mol of trimethoxysilane was added dropwise over 30 min. The temperature was then raised to 100°C and held for 3 h to terminate the reaction. After cooling, the crude product was obtained by filtration, weighing, and the content of hexadecyltrimethoxysilane was determined by gas chromatography. Simultaneously, the catalyst was filtered, washed with a small amount of methanol, and dried at 60°C for later use. The hydrosilylation rate was calculated as: hexadecyltrimethoxysilane content in the crude product / (1 - content of residual 1-hexadecene in the spectrum) * 100%. The results are shown in Table 1.

[0048] Table 1

[0049]

[0050] The crude products obtained by filtration after catalytic reaction using the catalysts of Examples 1-3 were colorless. Table 1 shows that the catalytic effect of the catalyst obtained in this invention in the first reaction was similar to that of the homogeneous Karstedt catalyst (with slightly better catalytic effect in some examples). Furthermore, the catalyst obtained in this invention did not show a significant decrease in the addition rate after three cycles, demonstrating high catalyst stability. No significant decrease in activity was observed after three cycles of reaction and separation / washing. The homogeneous catalysts Speier and Karstedt cannot be separated and recycled from the reaction system, and can only be reacted once. The crude products from both catalysts were golden yellow, and the Speier catalyst showed poorer catalytic effect.

[0051] 2. The catalyst obtained in the examples catalyzes the addition of allyl polyether to trimethoxysilane:

[0052] 39 g of allyl polyethylene glycol monomethyl ether (0.1 mol) (Zhejiang Huangma HMS-274M) was mixed with 10 ppm (based on Pt) of catalyst (Examples 1-3, Speier catalyst, Karstedt catalyst). After activation at 80 °C for 30 min under nitrogen protection, 13.42 g of trimethoxysilane (0.11 mol) was added dropwise. After the addition was complete, the temperature was raised to 110 °C until no significant reflux was observed in the system. The catalyst was then cooled and filtered to obtain a crude product. The crude product was then removed by vacuum distillation at 80 °C and -0.04 to -0.03 MPa to obtain the product. The product was weighed, and the hydrosilylation rate was calculated. The hydrosilylation rate = actual weight of product / theoretical weight of product * 100%, where the theoretical weight is calculated as the sum of the masses of 0.1 mol allyl polyether and 0.11 mol trimethoxysilane. Simultaneously, after the reaction was complete, the catalyst was filtered, washed with a small amount of methanol, and dried at 60 °C for later use.

[0053] The results are shown in Table 2.

[0054] Table 2

[0055]

[0056] The catalyst prepared in this embodiment of the invention, after catalyzing the addition reaction of allyl polyether with trimethoxysilane, yielded a nearly colorless crude product by filtration. The addition product of allyl polyether and trimethoxysilane, after vacuum distillation and heating at 150°C, did not exhibit yellowing. Table 2 shows that in the first reaction, the catalytic effect of the catalyst provided by this invention is similar to, or even slightly better than, that of the homogeneous catalyst in the prior art. Furthermore, the addition rate did not decrease significantly after three cycles of the catalyst. In contrast, the crude product of the homogeneous catalyst Speier and Karstedt after one reaction was golden yellow. After vacuum distillation to remove low-boiling point particles, the viscosity increased. Even after adsorption and decolorization with 0.5% (w / w) 600-mesh activated carbon, the color remained golden yellow and could not be removed, indicating excessive platinum residue in the system. The catalyst obtained by this invention also exhibits significant advantages in this catalytic reaction.

[0057] Finally, the method of this invention is merely a preferred embodiment and is not intended to limit the scope of protection of this invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of this invention should be included within the scope of protection of this invention.

Claims

1. A method for preparing a hydrosilylation reaction catalyst, characterized in that, Includes the following steps: 1) An aqueous solution of a water-soluble thickener is mixed and dispersed with a non-polar organic solvent to obtain a suspension; the non-polar organic solvent is an organic solvent that can form an azeotrope with water; 2) Add alkoxysilanol solution to the suspension obtained in step 1) to carry out hydrolysis reaction. After the reaction is completed, take the organic phase, remove water and obtain a mixture; the alkoxysilane in the alkoxysilanol solution is a mixture of vinyltrimethoxysilane and tetramethoxysilane, and the mass ratio of vinyltrimethoxysilane to tetramethoxysilane is (1~10):

1. 3) Add chloroplatinic acid alcohol solution to the mixture obtained in step 2) to carry out a coordination reaction. After the reaction is completed, take the precipitate, dry it, and you will get the product.

2. The preparation method according to claim 1, characterized in that, In step 1), the water-soluble thickener is carboxymethyl cellulose, polyvinyl alcohol, sodium polyacrylate, or polyacrylamide.

3. The preparation method according to claim 2, characterized in that, In step 1), the water-soluble thickener is carboxymethyl cellulose.

4. The preparation method according to claim 1, characterized in that, In step 1), the concentration of the aqueous solution of the water-soluble thickening agent is 9*10 -5 -2*10 -3 .

5. The preparation method according to claim 1, characterized in that, In step 1), the nonpolar organic solvent is one or more of n-hexane, cyclohexane, n-octane, isooctane, and toluene.

6. The preparation method according to claim 1, characterized in that, In step 2), the mass ratio of vinyltrimethoxysilane to tetramethoxysilane is (2~5):

1.

7. The preparation method according to claim 1, characterized in that, The amount of the aqueous solution of the water-soluble thickener mentioned in step 1) is 2 to 5.5 times the mass of the alkoxysilanol solution mentioned in step 2).

8. The preparation method according to claim 1, characterized in that, In step 2), the hydrolysis reaction is carried out at a temperature of 40-45°C for 1.5-2 hours.

9. The preparation method according to any one of claims 1 to 8, characterized in that, In step 3), the amount of chloroplatinic acid used in the chloroplatinic acid alcohol solution is 0.01% to 0.2% of the amount of the mixture obtained in step 2).

10. The hydrosilylation reaction catalyst obtained by the preparation method according to any one of claims 1 to 9.

11. The application of the hydrosilylation catalyst of claim 10 in the catalytic addition reaction of hydrogen-containing silanes with olefins.

Images