CN114029082A - Synthesis method and application of novel high-activity magnetic nanoparticles - Google Patents
Synthesis method and application of novel high-activity magnetic nanoparticles Download PDFInfo
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- 239000002122 magnetic nanoparticle Substances 0.000 title claims abstract description 20
- 230000000694 effects Effects 0.000 title claims abstract description 19
- 238000001308 synthesis method Methods 0.000 title claims abstract description 17
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 claims abstract description 80
- 239000003054 catalyst Substances 0.000 claims abstract description 44
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- 229910020637 Co-Cu Inorganic materials 0.000 claims abstract description 13
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- 239000002904 solvent Substances 0.000 claims description 31
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 30
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- 239000012298 atmosphere Substances 0.000 claims description 15
- 239000003513 alkali Substances 0.000 claims description 14
- QGUAJWGNOXCYJF-UHFFFAOYSA-N cobalt dinitrate hexahydrate Chemical compound O.O.O.O.O.O.[Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O QGUAJWGNOXCYJF-UHFFFAOYSA-N 0.000 claims description 13
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- 238000003786 synthesis reaction Methods 0.000 claims description 11
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- 230000015572 biosynthetic process Effects 0.000 claims description 10
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- 239000001301 oxygen Substances 0.000 claims description 10
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- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims description 7
- NWFNSTOSIVLCJA-UHFFFAOYSA-L copper;diacetate;hydrate Chemical compound O.[Cu+2].CC([O-])=O.CC([O-])=O NWFNSTOSIVLCJA-UHFFFAOYSA-L 0.000 claims description 7
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- 238000000926 separation method Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- 150000001875 compounds Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 239000010949 copper Substances 0.000 description 3
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- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- -1 alkyne compound Chemical group 0.000 description 2
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- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000007096 Glaser coupling reaction Methods 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
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- 238000005119 centrifugation Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000000599 controlled substance Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 150000004699 copper complex Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
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- 238000002474 experimental method Methods 0.000 description 1
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- 239000000203 mixture Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
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Classifications
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- B01J35/33—
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/76—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen
- C07C2/82—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen oxidative coupling
- C07C2/84—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen oxidative coupling catalytic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/24—Nitrogen compounds
Abstract
The invention discloses a synthesis method and application of novel high-activity magnetic nanoparticles, and belongs to the field of catalysis. The nano particles are Co-Cu-g-C3N4The magnetic nano-particles are high-activity magnetic nano-particles and Co-Cu high-activity magnetic nano-particles, and the nano-particles are used for catalyzing phenylacetylene oxidation couple. The catalyst synthesized by the technical scheme of the invention can be magnetically recovered, is convenient and quick to recycle, can be recycled for three times, and has the reaction yield kept above 90%; and the catalytic reaction condition is mild, and the reaction can be realized at room temperature.
Description
Technical Field
The invention relates to the field of catalysis, in particular to a synthesis method and application of novel high-activity magnetic nanoparticles.
Background
1, 3-conjugated diynes are important building blocks in organic synthesis and are widely present in a variety of natural products, drugs and bioactive molecules with anti-inflammatory, antifungal, anti-HIV and anti-cancer activities. Therefore, the synthesis research thereof has received a great deal of attention. As early as 1869, Glaser firstly reported that a 1, 3-conjugated diyne compound is constructed by a Cu-catalyzed terminal alkyne coupling reaction. To date, Cu-catalyzed Glaser coupling reaction and improved methods based thereon are still widely applied to the synthesis of conjugated diyne.
Although the Cu-catalyzed terminal alkyne coupling reaction can efficiently construct a terminal alkyne compound, the reaction is often carried out in a homogeneous system, the problems that the catalyst is not easy to separate and the catalyst cannot be recycled exist, and particularly in the field of drug synthesis, the residue of the catalyst Cu greatly restricts the application of the method in the pharmaceutical field. In contrast, the heterogeneous catalysis system has the advantages of easy recovery and recycling of the catalyst, and the possibility of catalyst residue in the reaction system is greatly reduced, so that the development of the heterogeneous catalysis terminal alkyne coupling reaction is of great significance in the field of drug synthesis.
In 2007, Mizuno et al (Keigo Kamata, Syuhei Yamaguchi, Miyuki Kotani, Kazuya Yamaguchi, and Noritaka Mizuno, Angew. chem. int. Ed.2008,47, 2407-containing 2410) reported that oxidation coupling reaction of double copper substituted g-hydroxyl aluminum ion silicotungstate catalyzed terminal alkyne, 1, 3-conjugated diyne compound was prepared in high yield, and the catalyst was recycled four times. The reaction is carried out at 100 ℃ and acetonitrile is used as a solvent.
2011 Oishi et al (Takamichi Oishi, Kazuya Yamaguchi, and Noritaka Mizuno, ACS Cat.,2011,1,1351) add Cu (OH)xLoaded on manganese oxide based on an octahedral molecular sieve for catalyzing the oxidative coupling of alkyne, the catalytic activity of the catalyst is not reduced after the catalyst is recycled for 13 times, but a controlled product toluene is used as a solvent in the reaction, the reaction temperature is up to 100 ℃,so that the reaction puts higher requirements on equipment in industrial production application.
In 2012, Cai et al (rubian Xiao, Ruiya Yao, and Mingzhong Cai, eur.j.org.chem.2012,4178-4184) used 3- (2-aminoethylamino) propyl-functionalized MCM-41-immobilized copper complex as a catalyst, air as an oxidant, dichloromethane as a solvent, and piperidine as a base to achieve the coupling reaction of the terminal alkyne at room temperature to produce the 1, 3-conjugated diyne, which was recovered and reused by centrifugation. However, in this method, the synthesis steps of the catalyst are complicated, dichloromethane with high toxicity is required to be used as a solvent, and piperidine, a controlled drug which is easy to prepare is required to be used as an alkali, so that the reaction still has the defect of being not green enough.
Therefore, the development of a novel heterogeneous catalyst and the realization of the synthesis of 1, 3-conjugated diyne compounds under mild conditions by using a green solvent as a reaction solvent remain a challenging research topic.
Disclosure of Invention
Aiming at the technical problems, the invention provides a synthesis method and application of novel high-activity magnetic nanoparticles.
The purpose of the invention can be realized by the following technical scheme:
first Co-Cu-g-C3N4The synthesis method of the high-activity magnetic nanoparticles comprises the following steps:
g to C3N4Adding cobalt nitrate hexahydrate and copper acetate monohydrate into a solvent, then carrying out an impregnation method under the condition of stirring to remove the solvent, and drying the solvent; and calcining, cooling and grinding the dried solid powder to obtain the target product.
Preferably, the method comprises the following steps: the solvent described herein includes, but is not limited to, water.
In a first synthesis method: g-C3N4The molar ratio of cobalt nitrate hexahydrate to copper acetate monohydrate is 30-50: 0.5-5: 0.01 to 3.
In some preferred embodiments: g-C3N4Nitric acid hexahydrateThe molar ratio of cobalt to copper acetate monohydrate is 35-45: 0.5-1.5: 0.05 to 0.15.
In a first synthesis method: the calcining temperature is 850-950 ℃, and the calcining time is 0.5-1.5 h; and the calcination is carried out by adopting a temperature programming mode, wherein the temperature rising rate is 3-8 ℃/min.
The second method for synthesizing Co-Cu high-activity magnetic nanoparticles comprises the following steps:
mixing cobalt nitrate hexahydrate and copper acetate, grinding into powder, and calcining the obtained powder to obtain the target product.
In a second synthesis method: the molar ratio of cobalt nitrate hexahydrate to copper acetate is 10-30: 1.
in some preferred embodiments: the molar ratio of cobalt nitrate hexahydrate to copper acetate is 10-20: 1.
in a second synthesis method: the calcining temperature is 850-950 ℃, and the calcining time is 0.5-1.5 h; and the calcination is carried out by adopting a temperature programming mode, wherein the temperature rising rate is 3-8 ℃/min.
The technical scheme of the invention is as follows: the synthesis method prepares Co-Cu-g-C3N4The application of the high-activity magnetic nano particles in catalyzing the phenylacetylene oxidative coupling.
The technical scheme of the invention is as follows: the Co-Cu high-activity magnetic nano-particle prepared by the synthesis method is applied to catalyzing the phenylacetylene oxidative coupling.
Co-Cu-g-C prepared by using synthesis method3N4The method for catalyzing the phenylacetylene oxidative coupling by the high-activity magnetic nano particles comprises the following steps: according to the method, phenylacetylene is used as a raw material, isopropanol is used as a solvent, an oxygen atmosphere is used as a reaction atmosphere, and the reaction is carried out for 10-12 hours under the action of alkali and a catalyst, so that a target product can be obtained.
In the above catalytic process: the mass ratio of phenylacetylene to the catalyst is 1-5: 1; preferably: the mass ratio of phenylacetylene to the catalyst is 2-4: 1.
in the above catalytic process: the alkali is potassium hydroxide, and the catalyst is Co-Cu-g-C3N4；
In the above catalytic process: the molar ratio of phenylacetylene to alkali is 1-3: 1.
A method for catalyzing phenylacetylene by using Co-Cu high-activity magnetic nanoparticles comprises the steps of taking phenylacetylene as a raw material, isopropanol as a solvent, taking an oxygen atmosphere as a reaction atmosphere, and reacting for 10-12 hours under the action of alkali and a catalyst to obtain a target product.
In the above catalytic process: the mass ratio of phenylacetylene to the catalyst is 1-5: 1; preferably: the mass ratio of phenylacetylene to the catalyst is 2-4: 1;
in the above catalytic process: the alkali is potassium hydroxide, and the catalyst is Co-Cu;
in the above catalytic process: the molar ratio of phenylacetylene to alkali is 1-3: 1.
The invention has the beneficial effects that:
the catalyst synthesized by the technical scheme of the invention can be magnetically recovered, is convenient and quick to recycle, can be recycled for three times, and has the reaction yield kept above 90%; and the catalytic reaction condition is mild, and the coupling of phenylacetylene can be realized at room temperature to obtain the 1, 3-conjugated diyne compound.
Drawings
FIG. 1 is a nuclear magnetic spectrum of the product of example 4.
Detailed Description
The invention is further illustrated by the following examples, without limiting the scope of the invention:
example 1, pure g-C3N4Preparation of the Material
Weighing 30g of melamine, putting the melamine into a porcelain boat, then putting the porcelain boat into a tube furnace for calcination, and adding the melamine into the porcelain boat in N2Under the atmosphere condition, the temperature is raised to 600 ℃ at the temperature raising rate of 5 ℃/min and is kept for 2 h. Automatically cooling to room temperature, grinding, and collecting3N4(yellow solid powder).
Example 2 Co-Cu-g-C3N4Preparation of
3.712g of g-C are weighed3N4(40mmol), cobalt nitrate hexahydrate 0.3504g (1.2mmol), copper acetate monohydrate 15.97mg (0.08mmol), mixed into a beaker, approximately 50mL deionized water was added and magnetons were added, then the beaker was placed on a constant temperature magnetic stirrer and the solvent was removed by dipping and dried. And putting the dried solid powder into a porcelain boat, calcining at 900 ℃, heating at a rate of 5 ℃/min, and keeping the temperature for 1 h. Cooling to room temperature after heating, grinding, and collecting mark as Co-Cu-g-C3N4The catalyst is black and magnetic solid powder.
Example 3 preparation of Co-Cu
1.8688g (6mmol) of cobalt nitrate hexahydrate, 0.0799g (0.4mmol) of copper acetate were weighed, mixed into a beaker, approximately 10mL of deionized water was added and magnetons were added, then the beaker was placed on a constant temperature magnetic stirrer and the solvent was removed by dipping and dried. And putting the dried solid powder into a porcelain boat, calcining at 900 ℃, heating at a rate of 5 ℃/min, and keeping the temperature for 1 h. After heating, cooling to room temperature, grinding, collecting and marking as Co-Cu, wherein the catalyst is silver.
Example 4 Co-Cu-g-C3N4(catalytic phenylacetylene oxidative coupling)
23 μ L of phenylacetylene (0.2mmol, 20.4mg) was weighed as a substrate, 11.2mg of potassium hydroxide (0.2mmol) was weighed as a base, 6mg of Co-Cu-g-C3N4Putting the catalyst into a 35mL sealed tube, adding magnetons, adding 1mL of Isopropanol (IPA) solvent, placing the sealed tube on a constant-temperature magnetic stirrer under the condition of oxygen atmosphere, stirring at room temperature for reaction for 12h, monitoring TCL after the reaction is finished, recovering the catalyst through a magnet, and drying in vacuum for recovery for later use. The obtained organic phase solvent is evaporated under reduced pressure, the obtained residue is separated by a chromatographic column, petroleum ether is used as a developing agent, the phenylacetylene content is 20.4mg, the separation yield is 98.5%, and the purity reaches 100%.
As in fig. 1, product nuclear magnetic data:1H NMR(400MHz,CDCl3)7.52-7.54(m,4H),7.35-7.39(m,2H),7.26-7.34(m,4H).
example 5 Co-Cu catalyzed oxidative coupling of phenylacetylene
Measuring 23 mu L of phenylacetylene (0.2mmol, 20.4mg) as a substrate, weighing 11.2mg of potassium hydroxide (0.2mmol) as an alkali and 6mg of Co-Cu as a catalyst, placing the substrate in a 35mL sealed tube, adding magnetons, adding 1mL of Isopropanol (IPA) as a solvent, placing the sealed tube on a constant-temperature magnetic stirrer under the condition of oxygen atmosphere, stirring the mixture at room temperature for reaction for 12 hours, detecting TCL after the reaction is finished, recovering the catalyst by using a magnet, and drying and recovering the catalyst in vacuum for later use. The obtained organic phase solvent was evaporated under reduced pressure, the obtained residue was subjected to column separation, petroleum ether was used as a developing solvent to obtain 8.9mg of diyne, the separation yield was 43.9%, and the purity was 100%.
Example 6 Co-Cu-g-C3N4Cycle experiment of catalytic phenylacetylene oxidative coupling reaction: 23 μ L of phenylacetylene (0.2mmol, 20.4mg) was weighed as a substrate, 11.2mg of potassium hydroxide (0.2mmol) was weighed as a base, 6mg of Co-Cu-g-C3N4Putting the catalyst into a 35mL sealed tube, adding magnetons, adding 1mL of Isopropanol (IPA) solvent, placing the sealed tube on a constant-temperature magnetic stirrer under the condition of oxygen atmosphere, stirring at room temperature for reaction for 12h, monitoring TCL after the reaction is finished, recovering the catalyst through a magnet, and drying in vacuum for recovery for later use. The obtained organic phase solvent is evaporated under reduced pressure, the obtained residue is separated by a chromatographic column, petroleum ether is used as a developing agent, the phenylacetylene content is 20.4mg, the separation yield is 98.5%, and the purity reaches 100%.
Cycle performance testing of the catalyst:
catalytic cycle 1: a clean and dry 35mL sealed tube was taken, the recovered catalyst, 23. mu.L of phenylacetylene (0.2mmol, 20.4mg), 11.2mg of potassium hydroxide (0.2mmol), 1mL of Isopropanol (IPA) solvent, and stirred at room temperature under oxygen atmosphere for reaction for 12h, after the reaction was completed, the catalyst was recovered by a magnet, and vacuum-dried and recovered for use. The obtained organic phase solvent is evaporated under reduced pressure, the obtained residue is separated by a chromatographic column, petroleum ether is used as a developing agent, 19.7mg of phenylacetylene is obtained, the separation yield is 96.2%, and the purity reaches 100%.
Catalytic cycle 2: a clean and dry 35mL sealed tube was taken, the recovered catalyst, 23. mu.L of phenylacetylene (0.2mmol, 20.4mg), 11.2mg of potassium hydroxide (0.2mmol), 1mL of Isopropanol (IPA) solvent, and stirred at room temperature under oxygen atmosphere for reaction for 12h, after the reaction was completed, the catalyst was recovered by a magnet, and vacuum-dried and recovered for use. The obtained organic phase solvent is evaporated under reduced pressure, the obtained residue is separated by a chromatographic column, petroleum ether is used as a developing agent, 19.6mg of phenylacetylene is obtained, the separation yield is 95.8%, and the purity reaches 100%.
Catalytic cycle 3: a clean and dry 35mL sealed tube was taken, the recovered catalyst, 23. mu.L of phenylacetylene (0.2mmol, 20.4mg), 11.2mg of potassium hydroxide (0.2mmol), 1mL of Isopropanol (IPA) solvent, and stirred at room temperature under oxygen atmosphere for reaction for 12h, after the reaction was completed, the catalyst was recovered by a magnet, and vacuum-dried and recovered for use. The obtained organic phase solvent is evaporated under reduced pressure, the obtained residue is separated by a chromatographic column, petroleum ether is used as a developing agent, 19.3mg of phenylacetylene is obtained, the separation yield is 94.5%, and the purity reaches 100%.
Claims (10)
1. Co-Cu-g-C3N4The synthesis method of the high-activity magnetic nanoparticles is characterized by comprising the following steps: the method comprises the following steps: g to C3N4Adding cobalt nitrate hexahydrate and copper acetate monohydrate into a solvent, then carrying out an impregnation method under the condition of stirring to remove the solvent, and drying the solvent; and calcining, cooling and grinding the dried solid powder to obtain the target product.
2. The method of synthesis according to claim 1, characterized in that: g-C3N4The molar ratio of the cobalt nitrate hexahydrate to the copper acetate monohydrate is30-50: 0.5-5: 0.01 to 3; preferably: g-C3N4The molar ratio of the cobalt nitrate hexahydrate to the copper acetate monohydrate is 35-45: 0.5-1.5: 0.05 to 0.15.
3. The method of synthesis according to claim 1, characterized in that: the calcining temperature is 850-950 ℃, and the calcining time is 0.5-1.5 h; and the calcination is carried out by adopting a temperature programming mode, wherein the temperature rising rate is 3-8 ℃/min.
4. A method for synthesizing Co-Cu high-activity magnetic nanoparticles is characterized by comprising the following steps: the method comprises the following steps:
mixing cobalt nitrate hexahydrate and copper acetate, grinding into powder, and calcining the obtained powder to obtain the target product.
5. The method of synthesis according to claim 4, characterized in that: the molar ratio of cobalt nitrate hexahydrate to copper acetate is 10-30: 1; preferably: the molar ratio of cobalt nitrate hexahydrate to copper acetate is 10-20: 1.
6. the method of synthesis according to claim 4, characterized in that: the calcining temperature is 850-950 ℃, and the calcining time is 0.5-1.5 h; and the calcination is carried out by adopting a temperature programming mode, wherein the temperature rising rate is 3-8 ℃/min.
7. The method of claim 1, wherein the synthetic method is used to prepare Co-Cu-g-C3N4The application of the high-activity magnetic nano particles in catalyzing the phenylacetylene oxidative coupling.
8. Co-Cu-g-C prepared by the synthesis method of claim 13N4The method for catalyzing the phenylacetylene oxidative coupling by the high-activity magnetic nano particles is characterized by comprising the following steps: according to the method, phenylacetylene is used as a raw material, isopropanol is used as a solvent, an oxygen atmosphere is used as a reaction atmosphere, and the reaction is carried out for 10-12 hours under the action of alkali and a catalyst, so that a target product can be obtained.
Preferably: the mass ratio of phenylacetylene to the catalyst is 1-5: 1; preferably: the mass ratio of phenylacetylene to the catalyst is 2-4: 1;
preferably: the alkali is potassium hydroxide, and the catalyst is Co-Cu-g-C prepared by the method of claim 13N4；
Preferably: the molar ratio of phenylacetylene to alkali is 1-3: 1.
9. The application of the Co-Cu high-activity magnetic nanoparticles prepared by the synthesis method of claim 5 in catalyzing phenylacetylene oxidative coupling.
10. A method for catalyzing phenylacetylene oxidative coupling by using Co-Cu high-activity magnetic nanoparticles prepared by the synthesis method of claim 4 is characterized in that: according to the method, phenylacetylene is used as a raw material, isopropanol is used as a solvent, an oxygen atmosphere is used as a reaction atmosphere, and the reaction is carried out for 10-12 hours under the action of alkali and a catalyst, so that a target product can be obtained;
preferably: the mass ratio of phenylacetylene to the catalyst is 1-5: 1; preferably: the mass ratio of phenylacetylene to the catalyst is 2-4: 1;
preferably: the alkali is potassium hydroxide, and the catalyst is Co-Cu prepared by the method of claim 4;
preferably: the molar ratio of phenylacetylene to alkali is 1-3: 1.
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