CN111841610B - Electron-rich single-atom Pt alloy intermetallic compound catalyst and preparation method thereof - Google Patents

Electron-rich single-atom Pt alloy intermetallic compound catalyst and preparation method thereof Download PDF

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CN111841610B
CN111841610B CN202010774268.6A CN202010774268A CN111841610B CN 111841610 B CN111841610 B CN 111841610B CN 202010774268 A CN202010774268 A CN 202010774268A CN 111841610 B CN111841610 B CN 111841610B
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electron
intermetallic compound
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compound catalyst
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CN111841610A (en
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韩云虎
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Northwestern Polytechnical University
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/24—Nitrogen compounds
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C07F7/1872—Preparation; Treatments not provided for in C07F7/20
    • C07F7/1876—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-C linkages

Abstract

The invention relates to an electron-rich single-atom Pt alloy intermetallic compound catalyst and a preparation method thereof, wherein the electron-rich single-atom Pt alloy intermetallic compound catalyst is prepared from metal M 'or metal oxide M' y O x The nano particles are used as templates, acetylacetone platinum is replaced into the surfaces of the nano spheres, the polymer is coated on the surfaces of the nano spheres, and the electron-rich monoatomic M alloy intermetallic compound catalyst loaded on the hollow carbon nitride is obtained by utilizing the in-situ limited migration effect of the polymer and the nano spheres and performing synchronous pyrolysis, transformation and etching. The prepared catalyst has Pt1-PtFe with small particle size and uniform size 3 The particle size of the nano particles is about 2nm, the microstructure and the appearance of the carrier are characterized by hollow carbon-nitrogen spheres, and the thickness is 0.5-2 nm. The electron-rich monatomic M alloy intermetallic compound catalyst prepared by the invention has excellent reaction effect when used for preparing silane compounds through hydrosilylation, and is superior to monatomic Pt catalysts prepared by conventional methods and commercial Pt/C catalysts. The invention has important practical significance for realizing the industrialization of the heterogeneous catalytic hydrosilation reaction.

Description

Electron-rich single-atom Pt alloy intermetallic compound catalyst and preparation method thereof
Technical Field
The invention belongs to the technical field of preparation of monatomic catalysts, and relates to an electron-rich monatomic Pt alloy intermetallic compound catalyst, a preparation method and application thereof,
background
The electronic structure of the active center of the metal plate is closely related to the performance of the catalyst. The improvement of the performance of catalysts by adjusting the electronic structure has received increasing attention, and particularly for noble metal catalysts such as Pt, pd, etc., the improvement of their catalytic activity has an important meaning for reducing the cost. As a member of noble metals, pt plays an indispensable role in the fields of homogeneous and heterogeneous catalysis. However, it is difficult to achieve a reduction in the amount of Pt while increasing the activity of the Pt-based catalyst. Currently, it is considered as an effective strategy to improve catalytic activity by adjusting the electronic structure of Pt center by inserting a heteroatom between Pt atoms of a Pt-based catalyst. And further realizes the partial or complete isolation of Pt atoms by controlling the doping amount of the heteroatom, thereby realizing the continuous controllable regulation of the electronic structure of the Pt center. Furthermore, the electronegativity of the dopant atoms is also important for regulating the electronic structure of the active centers. In recent years, monoatomic catalysts (SACs) having completely separated active sites have been attracting attention, but they have a disadvantage in that the distance between active sites is long and uncontrollable. Researchers have found that the reported SACs are generally coordinated by atoms O, N and S. The coordination of the high electronegativity atom leads to the reduction of the electron cloud density of the active center of the catalyst, which in turn leads to the deactivation or activity reduction of some important catalytic systems, especially reactions in the reduction system, because the electron-rich active center in the reduction system is more favorable for the reduction of the substrate molecules. The high electronegativity of O, N and the S atom tends to result in high oxidation states and electron deficient characteristics of the coordinated metal centers, thus limiting their application in these catalytic systems.
As one of the major catalytic applications in current large-scale industrial production, products of hydrosilylation reactions are widely used in the field of silicone chemistry, such as pressure sensitive adhesives, silicone surfactants, and the like. However, at present, both in basic research and in industrial production, the preparation of organosilanes is based predominantly on the catalytic preparation of homogeneous transition metal compounds. Especially the noble metal Pt, in industrial production, the hydrosilylation reaction is mainly carried out based on a homogeneous Pt-based compound, which results in the consumption of a large amount of the noble metal Pt. Heterogeneous catalysis is receiving increasing attention as a main research direction for industrial catalysis. However, the development of heterogeneous catalysts with the same activity as homogeneous catalysts still faces great challenges, especially under environmentally friendly and mild conditions.
Disclosure of Invention
Technical problem to be solved
Aiming at the problem that the existing hydrosilation reaction is mainly realized by utilizing a homogeneous Pt-based compound catalyst, a large amount of Pt is consumed, and the problem that the Pt-based catalyst in a heterogeneous catalyst is insufficient in activity is solved.
Technical scheme
An electron-rich monatomic Pt alloy intermetallic compound catalyst characterized by: alloy intermetallic compound catalyst Pt1-PtFe loaded on hollow carbon nitrogen and provided with isolated Pt sites 3 The active site is coordinated by a Fe atom with small electronegativity, so that an atomic Pt active center has the characteristic of being rich in electrons; the carrier hollow carbon nitrogen has the shape and appearance characteristics of a hollow spherical microstructure, and the loading amount of active metal Pt is 5wt%.
The particle size of the hollow sphere is about-2 nm.
A method for preparing the electron-rich monoatomic Pt alloy intermetallic compound catalyst by using an in-situ limited thermophoresis method is characterized by comprising the following steps of:
step 1: metal M 'or metal oxide M' y O x The nano particles and the metal salt M are dispersed in a DMF solvent, and are stirred for 1 to 3 hours at the temperature of between 100 and 130 ℃ to exchange the metal on the surfaces of the metal salt and the metal oxide nano particles;
step 2: adding a polymer monomer, stirring, adding DMF solution of another polymer monomer, stirring at constant temperature of 100-130 ℃ for 18-32h for carrying out sexual quaternization reaction to obtain a precursor coated with a polymer;
and step 3: pyrolyzing the collected precursor powder in an inert atmosphere, and then etching with acid to remove the metal oxide nanoparticle template to obtain the electron-rich monatomic M alloy intermetallic compound catalyst.
The metal salt M includes, but is not limited to, pt, pd, ir, or Ru.
The M' includes but is not limited to Fe, cu, mn, zn or Co.
Such polymers include, but are not limited to: quaternizing the resulting polymer, polypyrrole, polydopamine, melamine, polypyrrolidone or polyurethane.
The inert gas is nitrogen or argon.
The synthesized alloy intermetallic compound includes but is not limited to Pt and Fe, or Pd, ir, ru and Cu, mn, zn, co except Fe or Fe.
The application of the electron-rich monoatomic Pt alloy intermetallic compound catalyst is characterized in that: prepared Pt1-PtFe 3 the/CN material is suitable for hydrosilation reaction of olefin and its derivative, but is not limited to such reaction.
Advantageous effects
The invention provides an electron-rich single atom Pt alloy intermetallic compound catalyst and a preparation method thereof, wherein the electron-rich single atom Pt alloy intermetallic compound catalyst is prepared from metal M 'or metal oxide M' y O x The nano particles are used as a template, acetylacetone platinum is replaced into the surface of the nano sphere under the heating and stirring conditions, the surface of the nano sphere is coated with a polymer by utilizing the quaternization reaction, and the electron-rich monoatomic M alloy intermetallic compound catalyst loaded on the hollow carbon nitride is obtained by utilizing the in-situ limited domain migration effect of the polymer and the nano sphere and through synchronous pyrolysis, transformation and etching. The prepared catalyst has Pt1-PtFe with small particle size and uniform size 3 The particle size of the nano particles is about 2nm, the microstructure and the appearance of the carrier are characterized by hollow carbon-nitrogen spheres, and the thickness is 0.5-2 nm. The electron-rich monatomic M alloy intermetallic compound catalyst prepared by the invention has excellent reaction effect when used for preparing silane compounds through hydrosilylation, and is superior to monatomic Pt catalysts prepared by conventional methods and commercial Pt/C catalysts. The invention has important practical significance for realizing the industrialization of the heterogeneous catalytic hydrosilation reaction.
Drawings
FIG. 1 is an image under a transmission electron microscope of an electron-rich monatomic Pt alloy intermetallic compound catalyst prepared in example 1
FIG. 2 is an image of the electron-rich monoatomic Pt alloy intermetallic compound catalyst prepared in example 1 under a dark-field scanning transmission electron microscope
FIG. 3 is an image and an element distribution diagram of the high-angle annular dark-field scanning transmission electron microscope of the electron-rich monatomic Pt alloy intermetallic compound catalyst prepared in example 1
Detailed Description
The invention will now be further described with reference to the following examples and drawings:
a method for preparing the electron-rich monatomic Pt alloy intermetallic compound catalyst according to claim 1 or 2, by using an in-situ limited-area thermomigration method, characterized by the steps of:
step 1: metal (M ') or metal oxide (M' y O x ) Dispersing nanoparticles (M' = Fe, cu, mn, zn, co and the like) and metal salts (M = Pt, pd, ir, ru and the like) in a DMF solvent, stirring at the temperature of 100-130 ℃ for 1-3h, and then exchanging the metal salts with metals on the surfaces of the metal oxide nanoparticles;
step 2: adding a polymer monomer, continuously stirring for a period of time, adding a DMF solution of another polymer monomer, and stirring at a constant temperature of 100-130 ℃ for 18-32h to carry out quaternization reaction to obtain a precursor coated with a polymer;
and step 3: pyrolyzing the collected precursor powder in an inert atmosphere, and then etching with acid to remove the metal oxide nanoparticle template to obtain the electron-rich monatomic M alloy intermetallic compound catalyst.
Example 1
Fe 3 O 4 Preparing a template:
fe is prepared by a one-pot hydrothermal method 3 O 4 Nanospheres. 5.4g (20 mmol) of FeCl 3 ·6H 2 O was dissolved in 30mL of ethylene glycol and stirred vigorously at room temperature for 1h. Subsequently, after stirring for 0.5h, 10.0g of sodium acetate dissolved in 70mL of ethylene glycol was added. The mixture was then transferred to a hydrothermal kettle. After 12h of reaction at 200 ℃, the autoclave was cooled to room temperature. Washing the resulting Fe with ethanol and deionized water, respectively 3 O 4 The nanoparticles were run 3 times and then dried under vacuum for 12 h.
Fe 3 O 4 @Pt(acac) 2 Polymer:
mixing Pt (acac) 2 (39.33mg, 0.10mmol) in 10ml of DMF to give a clear yellow solution, which was then poured into 50ml of a solution in which 2g of Fe was dispersed 3 O 4 Nanoparticles in DMF. After stirring at 110 ℃ for 1 hour, 30ml of a DMF solution containing tri (4-imidozolylphenyl) amine (TIPA, 355mg, 0.8mmol) was added to the above-mentioned mixed solution, and further stirring was continued for 0.5 hour, after which a DMF solution of 30ml1,2,4,5-tetrakis (bromomethyl) bezene (TBMB, 279mg, 0.620 mmol) was further added and reacted at 110 ℃ for 24 hours. The resulting product was centrifuged, then washed three times with DMF, twice with ethanol and finally dried under vacuum at 80 ℃ overnight.
Pt1-PtFe 3 Preparation of/CN catalyst:
fe to be obtained 3 O 4 @Pt(acac) 2 Putting the polymer into a tube furnace, heating to 800 ℃ at a heating rate of 5 ℃/min in a flowing inert atmosphere for 3h, and naturally cooling to room temperature to obtain a sample. The sample obtained was then etched in 6M aqueous HCl at 60 ℃ for 24h to remove Fe 3 O 4 The template was collected by centrifugation, washed with water and finally dried under vacuum at 30 ℃ overnight.
Example 2
Pt1-PtFe prepared in example 1 3 ,/CN (5 mg, 4.6wt% Pt), 1-octene (4.46 mmol) and triethoxysilane (4.47 mmol) were added to a 15mL glass reaction tube. After 1.5h of reaction at 60 ℃, the mixture was extracted with ethyl acetate while recovering the solid catalyst by centrifugation. The products were analyzed by GC-MS and GC with n-dodecane as an internal standard. The conversion and selectivity of the reaction are in>99％。
Example 3
Pt1-PtFe prepared in example 1 3 ,/CN (5 mg, 4.6wt% Pt), 1-hexene (4.46 mmol) and triethoxysilane (4.47 mmol) were added to a 15mL glass reaction tube. After 1.5h of reaction at 60 ℃, the mixture was extracted with ethyl acetate while recovering the solid catalyst by centrifugation. The products were analyzed by GC-MS and GC with n-dodecane as an internal standard. Conversion and selectivity of the reaction>99％。
Example 4
Pt1-PtFe prepared in example 1 3 ,/CN (5 mg, 4.6wt% Pt), 1-dodecene (4.46 mmol) and triethoxysilane (4.47 mmol) were added to a 15mL glass reaction tube. After 1.5h of reaction at 60 ℃, the mixture was extracted with ethyl acetate while recovering the solid catalyst by centrifugation. The products were analyzed by GC-MS and GC with n-dodecane as an internal standard. The conversion and selectivity of the reaction are respectively>99% and>98％。
example 5
Pt1-PtFe prepared in example 1 3 /CN (5 mg, 4.6wt% Pt), 1-octadecene (4.46 mmol) and triethoxysilane (4.47 mmol) were added to a 15mL glass reaction tube. After reacting at 60 ℃ for 2h, the mixture was extracted with ethyl acetate while recovering the solid catalyst by centrifugation. The products were analyzed by GC-MS and GC with n-dodecane as an internal standard. The conversion and selectivity of the reaction are respectively>99% and>97％。
example 6
Pt1-PtFe prepared in example 1 3 /CN (5 mg, 4.6wt% Pt), 3,3' -dimethyl-1-butene (4.46 mmol) and triethoxysilane (4.47 mmol) were added to a 15mL glass reaction tube. After reacting at 60 ℃ for 3h, the mixture was extracted with ethyl acetate while recovering the solid catalyst by centrifugation. The products were analyzed by GC-MS and GC with n-dodecane as an internal standard. Conversion and selectivity of the reaction>99％。
Example 7
Pt1-PtFe prepared in example 1 3 ,/CN (5 mg, 4.6wt% Pt), methyl 10-undecenoate (4.46 mmol) and triethoxysilane (4.47 mmol) were added to a 15mL glass reaction tube. After 4h of reaction at 60 ℃, the mixture was extracted with ethyl acetate while recovering the solid catalyst by centrifugation. The products were analyzed by GC-MS and GC with n-dodecane as an internal standard. The conversion and selectivity of the reaction are respectively>99% and>97％。
example 8
Pt1-PtFe prepared in example 1 3 /CN (5 mg, pt 4.6 wt%), 1,2 epoxy-4-vinylcyclohexane (4.46 mmol) and triethoxysilane (4.46 mmol)4.47 mmol) was added to a 15mL glass reaction tube. After reacting at 70 ℃ for 3h, the mixture was extracted with ethyl acetate while recovering the solid catalyst by centrifugation. The products were analyzed by GC-MS and GC with n-dodecane as an internal standard. The conversion and selectivity of the reaction are respectively>97% and>99％。
example 9
Pt1-PtFe prepared in example 1 3 ,/CN (5 mg, 4.6wt% Pt), propenyl phenyl ether (4.46 mmol) and triethoxysilane (4.47 mmol) were added to a 15mL glass reaction tube. After 5h of reaction at 70 ℃, the mixture was extracted with ethyl acetate while recovering the solid catalyst by centrifugation. The products were analyzed by GC-MS and GC with n-dodecane as an internal standard. The conversion and selectivity of the reaction are respectively>99% and>99％。
example 10
Pt1-PtFe prepared in example 1 3 ,/CN (5 mg, 4.6wt% Pt), styrene (4.46 mmol) and triethoxysilane (4.47 mmol) were added to a 15mL glass reaction tube. After 6h of reaction at 70 ℃, the mixture was extracted with ethyl acetate while recovering the solid catalyst by centrifugation. The products were analyzed by GC-MS and GC with n-dodecane as an internal standard. The conversion and selectivity of the reaction are respectively>97% and>95％。
example 11
Pt1-PtFe prepared in example 1 3 ,/CN (5 mg, 4.6wt% Pt), p-chlorostyrene (4.46 mmol) and triethoxysilane (4.47 mmol) are added to a 15mL glass reaction tube. After 6h of reaction at 70 ℃, the mixture was extracted with ethyl acetate while recovering the solid catalyst by centrifugation. The products were analyzed by GC-MS and GC with n-dodecane as an internal standard. The conversion and selectivity of the reaction are respectively>96% and>97％。

Claims (6)

1. an electron-rich monatomic Pt alloy intermetallic compound catalyst characterized by: alloy intermetallic compound catalyst Pt1-PtFe loaded on hollow carbon nitrogen and provided with isolated Pt sites 3 The active site is coordinated by a Fe atom with small electronegativity, so that an atomic Pt active center has the characteristic of being rich in electrons; carrier (C)The hollow carbon and nitrogen of the body has the morphological characteristics of a hollow spherical microstructure, and the loading amount of active metal Pt is 5wt percent.
2. The electron-rich monatomic Pt alloy intermetallic compound catalyst according to claim 1, characterized in that: the particle size of the hollow sphere is 2nm.
3. A method for preparing the electron-rich monatomic Pt alloy intermetallic compound catalyst according to claim 1 or 2 by an in-situ limited thermophoresis method, characterized by the steps of:
step 1: metal M 'or metal oxide M' y O x The nano particles and the metal salt M are dispersed in a DMF solvent, and are stirred for 1 to 3 hours at the temperature of between 100 and 130 ℃ to exchange the metal on the surfaces of the metal salt and the metal oxide nano particles;
and 2, step: adding a polymer monomer, stirring, adding DMF solution of another polymer monomer, stirring at constant temperature of 100-130 ℃ for 18-32h for carrying out sexual quaternization reaction to obtain a precursor coated with a polymer;
and step 3: and pyrolyzing the collected precursor powder in an inert atmosphere, and then etching with acid to remove the metal oxide nano particle template to obtain the electron-rich monatomic M alloy intermetallic compound catalyst.
4. The method of claim 3, wherein: the polymer comprises: quaternizing the resulting polymer, polypyrrole, polydopamine, melamine, polypyrrolidone or polyurethane.
5. The method of claim 3, wherein: the inert gas is nitrogen or argon.
6. Use of the electron-rich monatomic Pt alloy intermetallic compound catalyst according to claim 1, characterized in that: prepared Pt1-PtFe 3 the/CN material is suitable for hydrosilation reaction of olefin and its derivative.
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CN113842936B (en) * 2021-10-22 2023-06-23 四川大学华西医院 Platinum-based monoatomic electrocatalytic material and preparation method and application thereof
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