CN110075900B - Palladium-loaded mesoporous carbon-silicon dioxide catalyst material, and preparation method and application thereof - Google Patents

Palladium-loaded mesoporous carbon-silicon dioxide catalyst material, and preparation method and application thereof Download PDF

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CN110075900B
CN110075900B CN201910358799.4A CN201910358799A CN110075900B CN 110075900 B CN110075900 B CN 110075900B CN 201910358799 A CN201910358799 A CN 201910358799A CN 110075900 B CN110075900 B CN 110075900B
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万颖
赵小瑞
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Shanghai Normal University
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    • B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
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Abstract

The invention relates to a palladium-loaded mesoporous carbon-silicon dioxide catalyst material and a preparation method and application thereof, wherein the method comprises the steps of taking soluble resin as a carbon source, an organic silicon source as an organic functional group source, a surfactant as a template, adding an inorganic silicon source, and preparing an amino-functionalized ordered mesoporous polymer-silicon oxide composite material by a multi-component co-assembly method; calcining to obtain an amino functionalized mesoporous carbon-silicon dioxide composite material; further, dipping and loading Pd, loading the Pd on the mesoporous composite material, and finally reducing to obtain the product. Compared with the prior art, the preparation method is simple and feasible, and the prepared palladium catalyst is used for catalyzing the reaction of synthesizing 8-methoxymethyl quinoline from 8-methylquinoline and methanol, so that the yield is high.

Description

Palladium-loaded mesoporous carbon-silicon dioxide catalyst material, and preparation method and application thereof
Technical Field
The invention belongs to the technical field of mesoporous material preparation, and particularly relates to a palladium-loaded mesoporous carbon-silica catalyst material, and a preparation method and application thereof.
Background
The palladium catalyst is an important reaction catalyst in the organic synthesis process and is widely applied to organic C-H bond activation reaction and fine chemical production. Palladium on carbon is a widely used commercial catalyst. However, the carbon material is an inert carrier, so that the bonding force between the carbon material and palladium is weak, and the catalyst has the problems of metal palladium loss, agglomeration, easy poisoning and inactivation and the like in the reaction process. Therefore, the invention of the palladium catalyst with stable structure and low cost has great significance for replacing the traditional palladium carbon catalyst.
The ordered mesoporous material has the advantages of high specific surface area, large pore volume and uniform pore diameter, and can be widely applied to the fields of adsorption, catalysis, separation and the like. The ordered mesoporous material is taken as a carrier to stabilize the palladium nano-particles, so that the defects can be effectively overcome, and the development of the ordered mesoporous material draws wide attention. The traditional method for preparing the metal catalyst is to load palladium nanoparticles by taking the ordered mesoporous material as a carrier in a post-loading mode. But the method can select carriers with proper pore structures and surface areas according to the requirements of physical and chemical properties of the catalyst, and enhance the mechanical properties, heat resistance and heat transfer performance of the catalyst; for the noble metal catalyst, the metal is uniformly dispersed on the large surface area, so that the using amount of the noble metal of the catalyst can be saved, and the cost of the catalyst is reduced; it is easy to adopt multi-component simultaneous load or utilize a certain function of the carrier to prepare the multifunctional catalyst. The synthesized organic functionalized hybrid mesoporous material can be functionalized on the surface of a pore and in the pore canal space, the functional group and palladium have stronger combination effect, palladium species can be dispersed and stabilized in the high-temperature carbonization process of the catalyst, and the final catalyst has high dispersion, smaller size and higher stability of palladium nano particles.
Patent CN102660028A discloses an organic group functionalized ordered mesoporous polymer material and a synthesis method thereof, wherein the material has high content of organic functional groups (0.1 wt% -15 wt%) and high specific surface area (200-500 m) 2 Per g) large pore volume (0.1-1.0 cm) 3 G) and uniform pore diameter (3-12 nm), and has a two-dimensional hexagonal or three-dimensional cubic mesostructure. The synthesis method comprises the following steps: under the acidic condition, carrying out prehydrolysis on an inorganic silicon source and an organic silicon source containing organic functional groups; then mixing with a nonionic surfactant; adding soluble resin to carry out self-assembly in organic solution to obtain the organic group functionalized-nonionic surfactant composite material. Removing the surfactant to obtain the organic group functionalized ordered mesoporous polymer material. The patent is not yet used for the preparation of an amino-functionalized carbon-silica supported palladium catalyst, and the prepared functionalized catalyst is not used for the reaction to carry out the verification of the performance of the catalyst.
Disclosure of Invention
The invention aims to solve the problems and provide a palladium-supported mesoporous carbon-silica catalyst material, a preparation method and application thereof.
The purpose of the invention is realized by the following technical scheme:
a preparation method of palladium-loaded mesoporous carbon-silicon dioxide catalyst material comprises the following steps,
the amino-functionalized ordered mesoporous polymer-silicon oxide composite material is prepared by taking soluble resin as a carbon source, an organic silicon source as an organic functional group source, a surfactant as a template and an inorganic silicon source through a multi-component co-assembly method;
calcining to obtain an amino functionalized mesoporous carbon-silicon dioxide composite material;
further, impregnating and loading Pd, and loading the Pd on the mesoporous composite material;
finally, the product is obtained through reduction.
Preferably, the resol resin is a resol with a molecular weight of 200-5000g/mol, and further preferably, the resol resin is a resol.
Preferably, the organic silicon source is selected from one or more of N, N-bis (3-trimethoxysilylpropyl) urea, 3-ureidopropyltrimethoxysilane, 3-ureidopropyltriethoxysilane, 3-aminopropyltrimethoxysilane and 3-aminopropyltriethoxysilane.
Preferably, the inorganic silicon source is selected from one or more of ethyl orthosilicate, methyl orthosilicate or propyl orthosilicate.
Preferably, the surfactant is a nonionic surfactant selected from one or more of a polyethylene oxide-polypropylene oxide triblock copolymer or an alkane-polyethylene oxide diblock copolymer surfactant having the general formula C a H 2a+1 EO b 、EO c PO d EO c Wherein a has a value in the range of 10 to 18, b is 5 to 25, c is 5 to 135, and d is 25 to 135; further preferably, the surfactant is C 16 H 33 EO 10 (Brij56)、 C 16 H 33 EO 20 、C 18 H 37 EO 10 (Brij76)、EO 20 PO 70 EO 20 (P123)、EO 106 PO 70 EO 106 (F127) Or EO 132 PO 50 EO 132 (F108) One or more of them. Surfactants are available from BASF or Sigma-Aldrich.
A preparation method of a palladium-loaded mesoporous carbon-silicon dioxide catalyst material specifically comprises the following steps:
(1) Dissolving a surfactant and hydrochloric acid mutually to obtain a solution A, hydrolyzing an inorganic silicon source and an organic silicon source by using an organic solvent to obtain a solution B, mixing the solution A and the solution B, adding soluble resin for reaction, and removing the organic solvent contained in a reactant to obtain a solid;
(2) Performing low-temperature thermosetting on the solid obtained in the step (1) to obtain a prefabricated material, and calcining the prefabricated material under the protection of inert atmosphere to remove a surfactant to obtain a catalyst material precursor;
(3) And (3) mixing the catalyst material precursor obtained in the step (2) with a palladium ion solution, filtering to obtain a solid, and reducing to obtain the palladium-loaded mesoporous carbon-silicon dioxide catalyst material.
Preferably, the organic solvent is selected from one or more of alcohols, benzenes, tetrahydrofuran, diethyl ether or dichloromethane;
in the step (1), the mass concentration of the surfactant is 0.5-25%, the concentration of the hydrochloric acid solution is 0.2-4 mol/L, the molar ratio of the inorganic silicon source to the organic silicon source is 1-20, more preferably 1-10, the molar ratio of the organic silicon source to the surfactant is 10-60, and the molar ratio of the soluble resin to the total silicon source is 0.01-0.6;
in the step (1), the hydrolysis temperature is 20-45 ℃, the hydrolysis time is 0.5-4h, the reaction temperature is 20-45 ℃, and the reaction time is 10min-4h.
Preferably, the low-temperature thermosetting temperature in the step (2) is 40-120 ℃, the low-temperature thermosetting time is 12-48h, the calcining temperature is 200-500 ℃, and the calcining temperature is 1-12h;
reducing by using hydrogen or reducing by using a formaldehyde solution, a sodium borohydride solution or a potassium borohydride solution at low temperature;
the palladium ion solution in the step (3) is selected from one or more of palladium acetate, palladium nitrate, dichlorodiammine palladium, dichlorotetraammine palladium, sodium chloropalladate or palladium chloride reagents.
The catalyst material prepared by the preparation method has a highly ordered two-dimensional hexagonal mesostructure and a specific surface area of 300-900 m 2 Per gram, pore volume of 0.30-2.0 cm 3 The pore diameter is 5.0-15.0 nm, the content of metal Pd is 1-10 wt%, and the size of Pd nano-particles is 1-5.0 nm.
The catalyst material is applied to the reaction of 8-methylquinoline and methanol to generate 8-methoxymethylquinoline.
The invention utilizes a solvent volatilization induction self-assembly technology, takes phenolic resin as a carbon source, 3-aminopropyltrimethoxysilane as an organic functional group source, tetraethoxysilane as an inorganic silicon source and triblock copolymer as a template to prepare the amino functionalized ordered mesoporous polymer-silicon oxide composite material by a multi-component co-assembly method. Further using Pd-N coordination to load Pd on the mesoporous polymer, and reducing Pd nano-particles by using a low-temperature sodium borohydride solution or high-temperature hydrogen to obtain the amino functionalized mesoporous carbon-silicon dioxide composite material loaded palladium catalyst. When the catalyst is used for catalyzing 8-methylquinoline and methanol to perform sp3C-H functionalization to construct a C-O bond to generate 8-methoxymethylquinoline, the yield of 87% can be obtained, which is higher than the optimal result (the yield is 77%) reported by the literature of a homogeneous catalyst.
Compared with the prior art, the invention has the following beneficial effects:
(1) The preparation method comprises the conventional operations of mixing, reacting, calcining, filtering and the like, is simple and easy to implement, adopts common medicines as raw materials, and has low cost;
(2) The prepared palladium catalyst has a two-dimensional hexagonal mesostructure, large specific surface area, large pore volume, uniform pore diameter, high content of supported palladium, small particle size of palladium nanoparticles and excellent structure;
(3) The palladium catalyst is used for the reaction of synthesizing 8-methoxymethyl quinoline from 8-methylquinoline and methanol, and the yield is high.
Drawings
FIG. 1 is a characteristic X-ray diffraction (XRD) pattern of a two-dimensional hexagonal (p 6 mm) carbon-silica material prepared in example 2;
FIG. 2 is a characteristic nitrogen adsorption-desorption isotherm plot of the two-dimensional hexagonal (p 6 mm) carbon-silica material prepared in example 2;
FIG. 3 is a characteristic X-ray diffraction (XRD) spectrum of the mesoporous carbon-palladium silica catalyst prepared in example 3;
FIG. 4 is a Transmission Electron Microscope (TEM) image of the mesoporous carbon-palladium silica catalyst prepared in example 3;
FIG. 5 is a characteristic X-ray diffraction (XRD) spectrum of the mesoporous carbon-palladium silica catalyst prepared in example 4;
fig. 6 is a characteristic X-ray diffraction (XRD) spectrum of the mesoporous carbon-palladium silica catalyst prepared in example 5.
Detailed Description
The invention is described in detail below with reference to the figures and specific embodiments.
Example 1
Placing 6.0g of phenol in a three-necked flask, and heating in a water bath at 50 ℃ to obtain a transparent liquid; 3.70g of sodium hydroxide solution with the mass percent of 20 percent is prepared and slowly dripped into the liquid. After 10 minutes, 15.0g of formaldehyde solution with the mass percent of 37 percent is added, the mixture is refluxed for 1 hour at the temperature of 90 ℃, cooled to the room temperature, and the pH value is adjusted to be neutral. Distilling under reduced pressure at 45-50 ℃ to obtain the residue which is the target product of phenolic resin. After cooling to room temperature, respectively preparing ethanol or ether solution of the phenolic resin prepolymer with the mass percentage concentration of 20-45wt% for later use.
Example 2
2.0g of F127 (EO) at 40-60 DEG C 106 PO 70 EO 106 ) The surfactant was dissolved in 10.0g of a methylene chloride solution, followed by addition of 1g of a 0.4mol/L hydrochloric acid solution and prehydrolysis with stirring for 1 hour to obtain a solution A. At the same temperature, in a solution of 10.0g of dichloromethane3.0g of ethyl orthosilicate, 1.2g of N, N-bis (3-trimethoxysilylpropyl) urea are added in sequence and stirred for 1 hour to obtain a solution B. After the solution A and the solution B are mixed, 20wt% of the phenolic resin synthesized in the step 1 is added, and magnetic stirring is carried out for 4 hours. A pale yellow clear solution was obtained. The solution is evenly spread on the surface of a glass culture dish and is placed for 2 hours at room temperature, then the temperature is raised to 100 ℃ for heat polymerization for 24 hours, and a light yellow transparent film is scraped off to obtain the prefabricated material.
And calcining the obtained prefabricated material at the temperature of 400 ℃ for 6 hours by using inert protective gas to remove the surfactant. The obtained material is the amino functionalized mesoporous carbon-silicon dioxide material. The material has a two-dimensional hexagonal structure (space group p6 mm), the pore diameter is 10nm, and the pore volume is 1.93cm 3 Per g, specific surface area 874m 2 (ii) in terms of/g. Its characteristic X-ray diffraction (XRD) pattern is shown in figure 1. The nitrogen adsorption-desorption isotherm diagram is shown in FIG. 2.
Example 3
2.0g of P123 (EO) at 40-60 ℃ 20 PO 70 EO 20 ) The surfactant was dissolved in 10.0g of tetrahydrofuran solution, followed by addition of 1g of 1mol/L hydrochloric acid solution and prehydrolysis with stirring for 1 hour to give solution A. At the same temperature, 3.6g of propyl orthosilicate and 1.0g of 3-ureidopropyltriethoxysilane were sequentially added to 10.0g of tetrahydrofuran solution, and the mixture was stirred for 1 hour to obtain solution B. After the solution A and the solution B were mixed, 20wt% of the phenolic resin synthesized in example 1 was added and magnetically stirred for 4 hours. A pale yellow clear solution was obtained. The solution is evenly spread on the surface of a glass culture dish and is placed for 2 hours at room temperature, then the temperature is raised to 100 ℃ for heat polymerization for 24 hours, and a light yellow transparent film is scraped off to obtain the prefabricated material. And calcining the prefabricated material at 400 ℃ for 6 hours by using inert shielding gas to remove the surfactant.
0.5g of the above solid sample was weighed into a moderate beaker and 2.2mL of palladium chloride solution (1 g/100 mL) was added. Sealing and placing the mixture in a constant temperature oscillator, and shaking the mixture uniformly at room temperature. Taking out, adding the sodium borohydride solution according to the proportion, and continuously adding the mixture into a constant-temperature oscillator to shake for half an hour. Taking out the sample, volatilizing the solvent in a room, and placing the sample in a vacuum drying oven at 80 ℃ to remove moisture and other impurities adsorbed on the surface of the sample after the solvent is volatilized. The sample was then placed in a tube furnace under hydrogen atmosphere at 300 ℃ for an additional 4 hours of reduction.
The obtained material is the mesoporous carbon-silicon dioxide material palladium catalyst, has a two-dimensional hexagonal structure (space group p6 mm), the aperture is 10.2nm, and the pore volume is 0.75cm 3 G, specific surface area 427m 2 The loading of palladium is 1 percent, and the size of the Pd nano-particles is 1.5nm.
Its characteristic X-ray diffraction (XRD) pattern is shown in figure 3. A Transmission Electron Microscope (TEM) image thereof is shown in FIG. 4.
43mg of palladium catalyst was placed in a 25mL round-bottom reaction flask, to which was added in this order 8-methylquinoline (59mg, 0.4 mmol), 142mg of iodobenzene acetate, 10mL of methanol as a solvent. The reaction mixture was stirred by connecting a spherical condenser tube and then placing it in an oil bath environment and raising the temperature to 150 ℃. After the reaction was completed, it was cooled to room temperature. The reaction solution was analyzed by gas chromatography to obtain 8-methoxymethylquinoline in a yield of 80%.
Example 4
3.2g of F108 (EO) at 40-60 ℃ 132 PO 50 EO 132 ) The surfactant was dissolved in 8.0g of toluene solution, then 1g of 2mol/L hydrochloric acid solution was added thereto, and prehydrolysis was carried out for 2 hours with stirring to obtain solution A. 3.5g of methyl orthosilicate and 0.6g of 3-ureidopropyltrimethoxysilane were added to 8.0g of the toluene solution in this order at the same temperature, and stirred for 2 hours to obtain a solution B. After the solution A and the solution B were mixed, 20wt% of the phenolic resin synthesized in example 1 was added and magnetically stirred for 2 hours. A pale yellow clear solution was obtained. The solution is evenly spread on the surface of a glass culture dish and is placed for 4 hours at room temperature, then the temperature is raised to 120 ℃ for heat polymerization for 24 hours, and a light yellow transparent film is scraped off to obtain the prefabricated material.
And calcining the prefabricated material at 400 ℃ for 6 hours by using inert shielding gas to remove the surfactant.
0.5g of the above solid sample was weighed into a moderate beaker and 6.6mL of palladium-nitrate solution (1 g/100 mL) was added. Sealing and placing in a constant temperature oscillator, and shaking uniformly at room temperature. And taking out the sample, volatilizing the solvent in a room, and placing the sample in a vacuum drying oven at 80 ℃ to remove moisture and other impurities adsorbed on the surface of the sample after the solvent is volatilized. The sample was then reduced in a tube furnace at 400 ℃ for 4 hours in a hydrogen atmosphere.
The obtained material is mesoporous carbon-silicon dioxide material supported palladium catalyst. Has a two-dimensional hexagonal structure (space group p6 mm), a pore diameter of 9.1nm and a pore volume of 0.92cm 3 G, specific surface area 580m 2 The supported amount of palladium is 3 percent, and the size of the Pd nano-particles is 3.5nm.
Its characteristic X-ray diffraction (XRD) pattern is shown in FIG. 5.
43mg of palladium catalyst was placed in a 25mL round-bottom reaction flask, to which 8-methylquinoline (59mg, 0.4 mmol), 142mg of iodobenzene acetate, 10mL of methanol as a solvent were added in this order. The spherical condenser was connected and then placed in an oil bath environment, and the temperature was raised to 150 ℃ to start the stirring reaction. After the reaction was completed, it was cooled to room temperature. The reaction solution was analyzed by gas chromatography to obtain 8-methoxymethylquinoline in a yield of 75%.
Example 5
2.0g of F127 surfactant was dissolved in 10.0g of the acetaldehyde solution at 40-60 ℃ and then 2g of 0.5mol/L hydrochloric acid solution was added and prehydrolysis was carried out under stirring for 1 hour to obtain solution A. 3.0g of propyl orthosilicate and 0.4g of 3-ureidopropyltrimethoxysilane were added to 10.0g of the acetaldehyde solution in this order at the same temperature, and stirred for 2 hours to obtain a solution B. After the solution A and the solution B were mixed, 20wt% of the phenolic resin synthesized in example 1 was added and magnetically stirred for 4 hours. A pale yellow clear solution was obtained. The solution is evenly spread on the surface of a glass culture dish and is placed for 1 hour at room temperature, then the temperature is raised to 100 ℃ for heat polymerization for 24 hours, and a light yellow transparent film is scraped off to obtain the prefabricated material.
And calcining the prefabricated material at 400 ℃ for 6 hours by using inert shielding gas to remove the surfactant.
0.5g of the above solid sample was weighed into a moderate beaker and 2.2mL of sodium chloropalladate solution (1 g/100 mL) was added. Sealing and placing in a constant temperature oscillator, and shaking uniformly at room temperature. Taking out, adding the potassium borohydride solution according to the proportion, and continuously adding the mixture into a constant-temperature oscillator to shake for half an hour. And taking out the sample, volatilizing the solvent in a room, and placing the sample in a vacuum drying oven at 80 ℃ to remove moisture and other impurities adsorbed on the surface of the sample after the solvent is volatilized. The sample was then placed in a tube furnace under hydrogen atmosphere at 300 ℃ for an additional 4 hours of reduction.
The obtained material is the mesoporous carbon-silicon dioxide material supported palladium catalyst. Has a two-dimensional hexagonal structure (space group p6 mm), a pore diameter of 7.2nm and a pore volume of 0.7cm 3 Specific surface area of 564 m/g 2 The loading of palladium is 1 percent, and the size of the Pd nano-particles is 1.0nm.
Its characteristic X-ray diffraction (XRD) pattern is shown in FIG. 6.
43mg of palladium catalyst was placed in a 25mL round-bottom reaction flask, to which was added in this order 8-methylquinoline (59mg, 0.4 mmol), 142mg of iodobenzene acetate, 10mL of methanol as a solvent. The reaction mixture was stirred by connecting a spherical condenser tube and then placing it in an oil bath environment and raising the temperature to 150 ℃. After the reaction was completed, it was cooled to room temperature. The reaction solution was analyzed by gas chromatography to obtain 8-methoxymethylquinoline in a yield of 87%.
The embodiments described above are intended to facilitate a person of ordinary skill in the art in understanding and using the invention. It will be readily apparent to those skilled in the art that various modifications to these embodiments may be made, and the generic principles described herein may be applied to other embodiments without the use of the inventive faculty. Therefore, the present invention is not limited to the above embodiments, and those skilled in the art should make improvements and modifications within the scope of the present invention based on the disclosure of the present invention.

Claims (6)

1. An application of a supported palladium mesoporous carbon-silicon dioxide catalyst material in the reaction of 8-methylquinoline and methanol to generate 8-methoxymethylquinoline is characterized in that the preparation method of the supported palladium mesoporous carbon-silicon dioxide catalyst material comprises the following steps:
the amino-functionalized ordered mesoporous polymer-silicon oxide composite material is prepared by taking soluble resin as a carbon source, an organic silicon source as an organic functional group source, a surfactant as a template and an inorganic silicon source through a multi-component co-assembly method;
calcining to obtain an amino functionalized mesoporous carbon-silicon dioxide composite material;
further, impregnating and loading Pd, and loading the Pd on the mesoporous composite material;
finally, reducing to obtain a product;
the organic silicon source is selected from one or more of N, N-bis (3-trimethoxysilylpropyl) urea, 3-ureidopropyltrimethoxysilane, 3-ureidopropyltriethoxysilane, 3-aminopropyltrimethoxysilane and 3-aminopropyltriethoxysilane;
the method specifically comprises the following steps:
(1) Mutually dissolving a surfactant solution and a hydrochloric acid solution to obtain a solution A, hydrolyzing an inorganic silicon source and an organic silicon source by using an organic solvent to obtain a solution B, mixing the solution A and the solution B, adding soluble resin for reaction, and removing the organic solvent contained in a reactant to obtain a solid;
(2) Performing low-temperature thermosetting on the solid obtained in the step (1) to obtain a prefabricated material, and calcining the prefabricated material under the protection of inert atmosphere to remove a surfactant to obtain a catalyst material precursor;
(3) Mixing the catalyst material precursor obtained in the step (2) with a palladium ion solution, filtering to obtain a solid, and reducing to obtain a palladium-loaded mesoporous carbon-silicon dioxide catalyst material, wherein the obtained catalyst material has a highly-ordered two-dimensional hexagonal mesostructure and a specific surface area of 300-900 m 2 A pore volume of 0.30 to 2.0 cm/g 3 The pore diameter is 5.0-15.0 nm, the content of metal Pd is 1-10 wt%, and the size of Pd nano-particles is 1-5.0 nm;
in the step (1), the hydrolysis temperature is 20-45 ℃, the hydrolysis time is 0.5-4h, the reaction temperature is 20-45 ℃, and the reaction time is 10min-4h;
in the step (2), the low-temperature thermosetting temperature is 40-120 ℃, the low-temperature thermosetting time is 12-48h, the calcining temperature is 200-500 ℃, and the calcining temperature is 1-12h.
2. The application of the supported palladium mesoporous carbon-silica catalyst material in the reaction of 8-methylquinoline and methanol to generate 8-methoxymethylquinoline according to claim 1, wherein the soluble resin is a soluble phenol-formaldehyde resin having a molecular weight of 200-5000 g/mol.
3. The application of the supported palladium mesoporous carbon-silica catalyst material in the reaction of 8-methylquinoline and methanol to generate 8-methoxymethylquinoline according to claim 1, wherein the inorganic silicon source is one or more selected from ethyl orthosilicate, methyl orthosilicate and propyl orthosilicate.
4. The application of the supported palladium mesoporous carbon-silica catalyst material in the reaction of 8-methylquinoline and methanol to generate 8-methoxymethylquinoline according to claim 1, wherein the surfactant is a nonionic surfactant selected from one or more surfactants of polyethylene oxide-polypropylene oxide-polyethylene oxide triblock copolymer or alkane-polyethylene oxide diblock copolymer, and the general formula of the surfactant is EO c PO d EO c 、C a H 2a+1 EO b Wherein a has a value in the range of 10 to 18, b is 5 to 25, c is 5 to 135, and d is 25 to 135.
5. The application of the supported palladium mesoporous carbon-silica catalyst material in the reaction of 8-methylquinoline and methanol to generate 8-methoxymethylquinoline according to claim 1,
the organic solvent is selected from one or more of alcohols, benzenes, tetrahydrofuran, diethyl ether or dichloromethane;
in the step (1), the mass concentration of the surfactant in the surfactant solution is 0.5-25%, the concentration of the hydrochloric acid solution is 0.2-4 mol/L, the molar ratio of the inorganic silicon source to the organic silicon source is 1-20, the molar ratio of the organic silicon source to the surfactant is 10-60, and the molar ratio of the soluble resin to the total silicon source is 0.01-0.6.
6. The application of the supported palladium mesoporous carbon-silica catalyst material in the reaction of 8-methylquinoline and methanol to generate 8-methoxymethylquinoline according to claim 1, wherein in the step (3), hydrogen reduction is adopted or formaldehyde solution, sodium borohydride solution or potassium borohydride solution is adopted for low-temperature reduction; the palladium ion solution in the step (3) is selected from one or more of palladium acetate, palladium nitrate, dichlorodiammine palladium, dichlorotetraammine palladium, sodium chloropalladate or palladium chloride reagents.
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