CN111054435B - Novel supported Pt catalyst, preparation method thereof and application thereof in hydrogen silicon addition - Google Patents
Novel supported Pt catalyst, preparation method thereof and application thereof in hydrogen silicon addition Download PDFInfo
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Abstract
The invention discloses a novel supported Pt catalyst, a preparation method thereof and application thereof in hydrogen silicon addition, belonging to the technical field of hydrogen silicon addition catalyst modification. Modifying perfluoroalkyl trialkoxysilane on the surface of the catalyst by adopting an impregnation method to prepare a novel supported Pt catalyst; the preparation method is simple and easy to realize, has the advantages of easily available raw materials and low cost, and can be used for industrial large-scale production. The novel supported Pt catalyst is used for hydrogen silicon hydrogenation, the reaction is successfully optimized from a kettle type reaction adopting a homogeneous catalyst to a continuous type reaction adopting a heterogeneous catalyst, and the process safety is better; the reaction conversion rate reaches 99mol%, the product selectivity is high, and the catalyst has a good application prospect.
Description
Technical Field
The invention belongs to the technical field of hydrogen silicon addition catalyst modification, and particularly relates to a novel supported Pt catalyst, a preparation method thereof and application thereof in hydrogen silicon addition.
Background
The fluorine-containing siloxane compound can react with hydroxyl on the surface of a base material to form a film with amphiphobic properties (oleophylic property and hydrophilic property), the film can prevent dirt such as water or oil from adhering, and the surface sliding property is increased, so that the surface wear resistance is improved, the film is a surface layer with antifouling and wear-resistant properties, and the film is widely applied to lenses, mobile phones, tablet computer display screens and the like at present.
At present, perfluoroalkyl siloxane compounds are mainly synthesized by performing hydrogen-silicon reaction on perfluoroalkyl ethylene and silane compounds, for example, in Chinese patent CN102070662A, perfluoroalkyl ethylene iodine is taken as a raw material, and trichlorosilane is continuously dripped for reaction in the presence of a noble metal catalyst to obtain an intermediate product; then adding a high boiling point solvent, continuously dripping methanol or ethanol for reaction, and carrying out vacuum rectification to obtain a target product, wherein the main defects are that the chemical activity of perfluoroalkyl ethylene in a reactant is poor, and the raw material has irritation and corrosivity. In addition, in order to achieve better antifouling and abrasion resistant effects, perfluorocarbon siloxanyl compounds with longer carbon chains must be prepared, but long-chain perfluorocarbons and derivatives thereof are more difficult to synthesize.
In comparison, long-chain perfluoropolyether is easy to obtain, but is usually synthesized by using a hydrogen-silicon reaction when reacting with a silane compound, for example, chinese patent CN102666759A adopts a more complicated synthesis route, firstly synthesizes a perfluoropolyether compound, then connects an allyl group to a carbon chain, finally connects a silane compound to the terminal of the propylene group and the silane compound under the action of a noble metal catalyst, and then obtains a fluoropolyether siloxane-based compound through an alcohol exchange reaction. The whole synthetic route is more complex, and reactants with irritation and corrosiveness are also used, so that the industrial production is not facilitated.
In the processes, the addition of the hydrogen silicon is an important step, the prior method adopts a Pt-containing complex catalyst to perform homogeneous reaction for intermittent operation, and the problems of the addition of the trichlorosilane and the like are involved, and the operation is very inconvenient due to the irritation and the corrosivity of the trichlorosilane. Meanwhile, the residue of the noble metal component Pt after the reaction also causes a problem of product quality due to the use of the complex catalyst of Pt.
Disclosure of Invention
The invention aims to provide a novel supported Pt catalyst which has excellent catalytic performance in a hydrogen silicon addition reaction. The invention also provides a preparation method of the novel supported Pt catalyst, which is simple and easy to realize, has the advantages of easily available raw materials and low cost, and can be industrially produced in a large scale. The invention also provides application of the novel supported Pt catalyst in hydrogen silicon hydrogenation, wherein the reaction conversion rate reaches 99mol%, the product selectivity is high, and the novel supported Pt catalyst has a good application prospect in hydrogen silicon hydrogenation.
In order to solve the problems, the technical scheme adopted by the invention is as follows:
dissolving fluorine substituted alkyl alkoxy silane compounds in a solvent to obtain a fluorine substituted alkyl alkoxy silane compound solution, adding a supported Pt catalyst into the solution for dipping treatment, removing the solvent after dipping, taking out a reaction product and drying to obtain a novel supported Pt catalyst; the dipping temperature is 20-25 ℃, and the dipping time is 0.5-0.8 h; the mass ratio of the metal platinum to the fluorine substituted hydrocarbyl alkoxy silane compound is 2: 1-1: 1; the solvent is perfluorobutyl ethyl ether, perfluoroisobutyl ethyl ether, perfluorohexane or perfluoroheptane; the dosage ratio of the fluorine substituted alkyl alkoxy silane compound to the solvent is 1-2 mg: 1mL; the drying condition is drying in 60-100 ℃ air atmosphere.
According to the preparation method of the novel supported Pt catalyst, the Pt content in the supported Pt catalyst is 0.1-2 wt.%.
According to the preparation method of the novel supported Pt catalyst, the fluorine substituted hydrocarbyl alkoxy silane compound is perfluoro hydrocarbyl trialkoxy silane.
According to the preparation method of the novel supported Pt catalyst, the perfluoroalkyl trialkoxysilane is perfluorooctyl trimethoxysilane, perfluorooctyl triethoxysilane, perfluorononyl trimethoxysilane, perfluorononyl triethoxysilane, perfluorodecyl trimethoxysilane or perfluorodecyl triethoxysilane.
The preparation method of the novel supported Pt catalyst comprises the following steps:
(1) Adding an oxide carrier into chloroplatinic acid or chloroplatinate solution for equal volume impregnation, stirring at room temperature for 25-35 min, then placing in a water bath at 75-85 ℃ for drying by distillation, then placing in an oven for drying at 100-120 ℃ for 10-14 h, and then roasting at 300-500 ℃ for 2-4 h in an air atmosphere;
(2) Placing the roasted product into a quartz tube, heating at 400-600 ℃, introducing air carrying water vapor at 75-85 ℃ for dechlorination for 5-7 h, wherein the air flow is 25-35 mL/min; then pure hydrogen is adopted to reduce for 2 to 4 hours at the temperature of 300 to 500 ℃; and (4) obtaining the supported Pt catalyst after reduction.
According to the preparation method of the novel supported Pt catalyst, the oxide carrier is silicon oxide, aluminum oxide or a silicon-aluminum-containing molecular sieve.
The novel supported Pt catalyst is prepared by the preparation method of the novel supported Pt catalyst.
The novel supported Pt catalyst is applied to the hydrogen-silicon addition reaction.
The novel supported Pt catalyst is added into a catalyst bed layer of a fixed bed reactor, and then trichlorosilane and perfluoropolyether propylene (CF) are added 3 CF 2 CF 2 -(OCF 2 CFCF 3 )n-O-CF 2 CF 2 -CH 2 OCH 2 CH＝CH 2 ) The perfluorobutyl ethyl ether solution flows through a catalyst bed layer to carry out hydrogen-silicon hydrogenation reaction to obtain a product; the reaction temperature is 40-60 ℃; the concentration of the perfluoropolyether propylene is 5%; the mol ratio of the trichlorosilane to the perfluoropolyether propylene is 4-6: 1.
The novel supported Pt catalyst is applied to the hydrogen-silicon addition reaction, and the molecular weight of the perfluoropolyether propylene is 5000.
Has the advantages that: compared with the prior art, the invention has the advantages that:
(1) The invention adopts an impregnation method to modify perfluoroalkyl trialkoxysilane on the surface of the catalyst to prepare the novel supported Pt catalyst, successfully realizes the optimization of the reaction from kettle type reaction adopting a homogeneous catalyst to continuous type reaction adopting a heterogeneous catalyst, and has better process safety.
(2) The novel supported Pt catalyst is used in hydrogen silicon hydrogenation, the conversion rate reaches 99mol%, the conversion is almost complete, and the product selectivity is very high, which indicates that the novel supported Pt catalyst has good application prospect in hydrogen silicon hydrogenation reaction.
(3) The preparation method of the novel supported Pt catalyst is simple and easy to realize, has the advantages of easily obtained raw materials and low cost, and can be used for industrial large-scale production.
Detailed Description
In order to make the aforementioned objects, features and advantages of the present invention more comprehensible, embodiments accompanying specific embodiments of the present invention are described in detail below.
Example 1
Configuration H 2 PtCl 6 30ml of the solution containing 0.1g of metal platinum, 10g of SiO were weighed 2 Adding the carrier into the solution, stirring at room temperature for 30min, evaporating in 80 deg.C water bath, drying in oven at 100 deg.C for 12 hr, and baking in muffle furnace at 400 deg.C for 2 hr. Dechlorination is carried out, the sample is placed into a quartz tube to be heated at 500 ℃, and dechlorination is carried out for 6 hours by introducing air at 30mL/min with water vapor at 80 ℃. H 2 Reducing for 2h at 400 ℃ under the reducing condition with the flow rate of 40 mL/min. Pt content 1wt.% in the catalyst. Adding 0.05g of perfluorodecyl trimethoxy silane into 30ml of perfluorobutyl ethyl ether to prepare a solution, soaking the catalyst in the solution at 20 ℃ for 0.5h, removing the solvent by using a rotary evaporator, taking out the catalyst, and drying the catalyst at 80 ℃ to obtain a modified catalyst, which is marked as a novel supported Pt catalyst A. After catalyst sheeting, the water contact angle was measured to be 115 degrees, indicating that perfluorodecyltrimethoxysilane had been modified onto the catalyst surface.
Example 2
Configuration H 2 PtCl 6 30ml of the solution containing 0.1g of metal platinum, 10g of Al was weighed 2 O 3 Adding the carrier into the solution, stirring at room temperature for 30min, evaporating in 80 deg.C water bath, drying in oven at 100 deg.C for 12h, and baking in muffle furnace at 400 deg.C for 2h. Dechlorination is carried out, the sample is placed into a quartz tube to be heated at 500 ℃, and dechlorination is carried out for 6 hours by introducing air at 30mL/min with water vapor at 80 ℃. H 2 Reducing for 2h at 400 ℃ under the reducing condition with the flow rate of 40 mL/min. Pt content in catalyst 1wt.%. 0.05g of perfluorodecyltrimethoxysilane was addedAnd (3) adding the catalyst into 30ml of perfluorobutyl ethyl ether to prepare a solution, soaking the catalyst for 0.5h at 20 ℃, removing the solvent by using a rotary evaporator, taking out the catalyst, and drying the catalyst at 80 ℃ to obtain a modified catalyst, wherein the modified catalyst is marked as a novel supported Pt catalyst B. After catalyst sheeting, the water contact angle was measured to be 115 degrees, indicating that perfluorodecyltrimethoxysilane had been modified onto the catalyst surface.
Example 3
Configuration H 2 PtCl 6 30ml of solution containing 0.1g of metal platinum, weighing 10g of ZSM-5 molecular sieve carrier, adding the carrier into the solution, stirring the solution for 30min at room temperature, then placing the solution in a water bath at 80 ℃ to dry, then placing the solution in an oven to dry for 12h at 100 ℃, and roasting the dried solution in a muffle furnace for 2h at 400 ℃. Dechlorination is carried out, the sample is placed into a quartz tube to be heated at 500 ℃, and dechlorination is carried out for 6 hours by introducing air at 30mL/min with water vapor at 80 ℃. H 2 Reducing for 2h at 400 ℃ under the reducing condition with the flow rate of 40 mL/min. Pt content 1wt.% in the catalyst. Adding 0.05g of perfluorodecyltrimethoxysilane into 30ml of perfluorobutylethyl ether to prepare a solution, soaking the catalyst in the solution at 20 ℃ for 0.5h, removing the solvent by using a rotary evaporator, taking out the catalyst, and drying the catalyst at 80 ℃ to obtain a modified catalyst, and marking as a novel supported Pt catalyst C. After catalyst sheeting, the water contact angle was measured to be 114 °, indicating that perfluorodecyltrimethoxysilane had modified the catalyst surface.
Example 4
Configuration H 2 PtCl 6 And (3) weighing 10g of SBA-15 carrier and adding the SBA-15 carrier into 30ml of solution containing 0.1g of metal platinum, stirring the solution at room temperature for 30min, drying the solution by evaporation in a water bath at 80 ℃, drying the solution in an oven at 100 ℃ for 12h, and roasting the dried solution in a muffle furnace at 400 ℃ for 2h. And dechlorinating, namely putting the sample into a quartz tube, heating at 500 ℃, and dechlorinating for 6 hours by introducing air at 30mL/min with 80 water vapor. H 2 Reducing for 2h at 400 ℃ under the reducing condition with the flow rate of 40 mL/min. Pt content 1wt.% in the catalyst. Adding 0.05g perfluorodecyltrimethoxysilane into 30ml perfluorobutylethyl ether to prepare a solution, immersing the above catalyst therein at 20 deg.C for 0.5 hr, removing solvent with rotary evaporator, and taking out the catalystAnd drying at 80 ℃ to obtain the modified catalyst which is marked as a novel supported Pt catalyst D. After catalyst sheeting, the water contact angle was measured to be 115 deg., indicating that perfluorodecyltrimethoxysilane had been modified onto the catalyst surface.
Example 5
Configuration H 2 PtCl 6 30ml of the solution containing 0.1g of metal platinum, 10g of SiO were weighed 2 Adding the carrier into the solution, stirring at room temperature for 30min, evaporating in 80 deg.C water bath, drying in oven at 100 deg.C for 12 hr, and baking in muffle furnace at 400 deg.C for 2 hr. And dechlorinating, namely putting the sample into a quartz tube, heating at 500 ℃, and dechlorinating for 6 hours by introducing air of 30mL/min with water vapor at 80 ℃. H 2 Reducing for 2h at 400 ℃ under the reducing condition with the flow rate of 40 mL/min. Pt content 1wt.% in the catalyst. Adding 0.05g of perfluorooctyltrimethoxysilane into 30ml of perfluorobutyl ethyl ether to prepare a solution, soaking the catalyst in the solution at 20 ℃ for 0.5h, removing the solvent by using a rotary evaporator, taking out the catalyst, drying at 80 ℃ to obtain a modified catalyst, and marking as a novel supported Pt catalyst E. After catalyst compression, the water contact angle was measured to be 115 deg., indicating that perfluorooctyltrimethoxysilane had modified the catalyst surface.
Example 6
Configuration H 2 PtCl 6 30ml of the solution containing 0.1g of metal platinum, 10g of SiO were weighed 2 Adding the carrier into the solution, stirring at room temperature for 30min, evaporating in 80 deg.C water bath, drying in oven at 100 deg.C for 12h, and baking in muffle furnace at 400 deg.C for 2h. Dechlorination is carried out, the sample is placed into a quartz tube to be heated at 500 ℃, and dechlorination is carried out for 6 hours by introducing air at 30mL/min with water vapor at 80 ℃. H 2 Reducing for 2h at 400 ℃ under the reducing condition with the flow rate of 40 mL/min. Pt content 1wt.% in the catalyst. Adding 0.05g of perfluorooctyltrimethoxysilane into 30ml of perfluorobutyl ethyl ether to prepare a solution, soaking the catalyst for 0.5h at 20 ℃, removing the solvent by using a rotary evaporator, taking out the catalyst, drying at 80 ℃ to obtain a modified catalyst, and marking as a novel supported Pt catalyst F. After the catalyst was tableted, the water contact angle was measured to be 114 °, indicating perfluorooctyl trisMethoxysilanes have been modified to the catalyst surface.
Example 7
Configuration H 2 PtCl 6 30ml of the solution containing 0.05g of metal platinum, 10g of SiO were weighed 2 Adding the carrier into the solution, stirring at room temperature for 30min, evaporating in 80 deg.C water bath, drying in oven at 100 deg.C for 12 hr, and baking in muffle furnace at 400 deg.C for 2 hr. Dechlorination is carried out, the sample is placed into a quartz tube to be heated at 500 ℃, and dechlorination is carried out for 6 hours by introducing air at 30mL/min with water vapor at 80 ℃. H 2 Reducing for 2h at 400 ℃ under the reducing condition with the flow rate of 40 mL/min. Pt content in the catalyst was 0.05wt.%. Adding 0.05G of perfluorodecyltrimethoxysilane into 30ml of perfluorobutylethyl ether to prepare a solution, soaking the catalyst for 0.5h at 20 ℃, removing the solvent by using a rotary evaporator, taking out the catalyst, drying at 80 ℃ to obtain a modified catalyst, and marking as a novel supported Pt catalyst G. After catalyst sheeting, the water contact angle was measured to be 115 deg., indicating that perfluorodecyltrimethoxysilane had been modified onto the catalyst surface.
The catalyst performance evaluation was carried out on a fixed bed reactor. 1g of novel supported Pt catalyst, trichlorosilane and CF 3 CF 2 CF 2 -(OCF 2 CFCF 3 )n-O-CF 2 CF 2 -CH 2 OCH 2 CH＝CH 2 (molecular weight 5000) Perfluorobutylethyl ether solution was passed through the catalyst bed at a flow rate of 5ml/h, wherein CF 3 CF 2 CF 2 -(OCF 2 CFCF 3 )n-O-CF 2 CF 2 -CH 2 0CH 2 CH＝CH 2 (the molecular weight is 5000) is 5 percent, the molar ratio of the trichlorosilane to the trichlorosilane is 5: 1, and the reaction temperature is 40 ℃. And collecting the product, and analyzing the content by using a nuclear magnetic resonance spectrum. The following table shows the evaluation results of the above catalysts.
TABLE 1 results of hydrogen-silicon addition reaction with different catalysts
| Catalyst and process for preparing same | Conversion in mol% | Selectivity mol% |
| A | 98 | 99.1 |
| B | 97 | 99.3 |
| C | 72 | 99.5 |
| D | 99 | 99.2 |
| E | 98 | 99.4 |
| F | 98 | 99.1 |
| G | 90 | 99.6 |
While the invention has been described in connection with preferred embodiments, it is to be understood that the invention is not limited to these illustrative embodiments, but may be variously modified by those skilled in the art without departing from the spirit and scope of the invention.
Claims (6)
1. The application of the modified supported Pt catalyst in hydrogen silicon addition reaction is characterized in that the modified supported Pt catalyst is added into a catalyst bed layer of a fixed bed reactor, and then a perfluorobutyl ethyl ether solution of trichlorosilane and perfluoropolyether propylene flows through the catalyst bed layer to carry out hydrogen silicon addition reaction to obtain a product; the reaction temperature is 40 to 60 ℃; the concentration of perfluoropolyether propylene was 5%; the molar ratio of trichlorosilane to perfluoropolyether propylene is 4-6;
the preparation method of the modified supported Pt catalyst comprises the following steps: dissolving fluorine substituted hydrocarbyl alkoxy silane compounds in a solvent to obtain a fluorine substituted hydrocarbyl alkoxy silane compound solution, adding a supported Pt catalyst into the solution for dipping treatment, removing the solvent after dipping, taking out a reaction product and drying to obtain a modified supported Pt catalyst; the dipping temperature is 20 to 25 ℃, and the dipping time is 0.5 to 0.8h; the mass ratio of the metal platinum to the fluorine-substituted hydrocarbyl alkoxy silane compound is (2); the solvent is perfluorobutyl ethyl ether, perfluoroisobutyl ethyl ether, perfluorohexane or perfluoroheptane; the dosage ratio of the fluorine substituted alkyl alkoxy silane compound to the solvent is 1 to 2 mg; the drying condition is that the mixture is dried in the air atmosphere of 60 to 100 ℃;
the preparation of the supported Pt catalyst comprises the following steps:
(1) Adding the oxide carrier into a chloroplatinic acid or chloroplatinic acid salt solution for equal volume impregnation, stirring at room temperature for 25-35 min, then placing in a water bath at 75-85 ℃, drying by distillation, then placing in an oven at 100-120 ℃, drying for 10-14 h, and then roasting at 300-500 ℃ in an air atmosphere for 2-4 h;
(2) Putting the roasted product into a quartz tube, heating at 400-600 ℃, introducing air carrying water vapor at 75-85 ℃ for dechlorination for 5-7 h, wherein the air flow is 25-35 mL/min; then pure hydrogen is adopted for reduction for 2 to 4 hours at the temperature of 300 to 500 ℃; and reducing to obtain the supported Pt catalyst.
2. The application of the modified supported Pt catalyst in the hydrogen-silicon addition reaction according to claim 1 is characterized in that the Pt content in the supported Pt catalyst is 0.1-2 wt.%.
3. The use of the modified supported Pt catalyst of claim 1 in a hydrogen-silicon addition reaction, wherein the fluorine substituted hydrocarbyl alkoxysilane compound is a perfluoro hydrocarbyl trialkoxysilane.
4. The use of the modified supported Pt catalyst of claim 3 in a hydrogen-silicon addition reaction, wherein the perfluoroalkyl trialkoxysilane is perfluorooctyltrimethoxysilane, perfluorooctyltriethoxysilane, perfluorononyltrimethoxysilane, perfluorononyltriethoxysilane, perfluorodecyltrimethoxysilane, or perfluorodecyltriethoxysilane.
5. The application of the modified supported Pt catalyst in the hydrogen-silicon addition reaction is characterized in that the oxide carrier is silicon oxide, aluminum oxide or a silicon-aluminum-containing molecular sieve.
6. The use of the modified supported Pt catalyst of claim 1 in a hydrogen-silicon addition reaction, wherein the molecular weight of the perfluoropolyether propylene is 5000.
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