CN113181913A - Copper-carbon composite catalyst and preparation method thereof - Google Patents
Copper-carbon composite catalyst and preparation method thereof Download PDFInfo
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- 239000003054 catalyst Substances 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 239000002131 composite material Substances 0.000 title claims abstract description 13
- AHADSRNLHOHMQK-UHFFFAOYSA-N methylidenecopper Chemical compound [Cu].[C] AHADSRNLHOHMQK-UHFFFAOYSA-N 0.000 title claims abstract description 13
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229910052802 copper Inorganic materials 0.000 claims abstract description 27
- 239000010949 copper Substances 0.000 claims abstract description 27
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 14
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 14
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims abstract description 12
- 238000000227 grinding Methods 0.000 claims abstract description 12
- 239000002105 nanoparticle Substances 0.000 claims abstract description 12
- 239000000758 substrate Substances 0.000 claims abstract description 9
- 238000005406 washing Methods 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000001413 amino acids Chemical class 0.000 claims abstract description 8
- 150000001879 copper Chemical class 0.000 claims abstract description 8
- 239000011780 sodium chloride Substances 0.000 claims abstract description 7
- 239000001103 potassium chloride Substances 0.000 claims abstract description 6
- 235000011164 potassium chloride Nutrition 0.000 claims abstract description 6
- 239000011258 core-shell material Substances 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims description 11
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 claims description 7
- 235000001014 amino acid Nutrition 0.000 claims description 7
- 238000005303 weighing Methods 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 claims description 4
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 claims description 4
- 229940112669 cuprous oxide Drugs 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 3
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 3
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 3
- 235000004279 alanine Nutrition 0.000 claims description 3
- 235000003704 aspartic acid Nutrition 0.000 claims description 3
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 3
- 229940116318 copper carbonate Drugs 0.000 claims description 3
- 229910000365 copper sulfate Inorganic materials 0.000 claims description 3
- 229910000009 copper(II) carbonate Inorganic materials 0.000 claims description 3
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 3
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 claims description 3
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 3
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 claims description 3
- 235000019854 cupric carbonate Nutrition 0.000 claims description 3
- 239000011646 cupric carbonate Substances 0.000 claims description 3
- 235000013922 glutamic acid Nutrition 0.000 claims description 3
- 239000004220 glutamic acid Substances 0.000 claims description 3
- 239000004471 Glycine Substances 0.000 claims description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims description 2
- 235000005772 leucine Nutrition 0.000 claims description 2
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 13
- 238000006243 chemical reaction Methods 0.000 abstract description 7
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 abstract description 4
- 238000001354 calcination Methods 0.000 abstract description 4
- 239000012279 sodium borohydride Substances 0.000 abstract description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract description 3
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000005470 impregnation Methods 0.000 description 5
- 238000000975 co-precipitation Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 238000001878 scanning electron micrograph Methods 0.000 description 3
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000005750 Copper hydroxide Substances 0.000 description 1
- 241000784732 Lycaena phlaeas Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910001956 copper hydroxide Inorganic materials 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002923 metal particle Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000005832 oxidative carbonylation reaction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
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Classifications
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/72—Copper
-
- 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
- B01J27/20—Carbon compounds
- B01J27/232—Carbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
The invention provides a copper-carbon composite catalyst and a preparation method thereof. The method takes common amino acid as a carbon source, copper salt as a copper source and sodium chloride or potassium chloride as a template, and prepares the copper-carbon composite catalyst through simple grinding, oxygen-free calcination and water washing. The copper nanoparticles are uniformly loaded on the surface of the carbon substrate, the carbon substrate is flaky, the size is 0.5-5mm, the copper nanoparticles are easy to filter and remove, and the copper nanoparticles are in a core-shell structure and have the size of 100-500 nm. The copper-carbon composite catalyst can be used for reducing p-nitrophenol, sodium borohydride is used as the catalyst, the reaction can be completed within a few minutes at room temperature, the catalytic activity is high, the reaction operation is simple, and the treatment is easy.
Description
Technical Field
The invention belongs to the field of copper catalysts, and particularly relates to a copper-carbon composite catalyst and a preparation method thereof.
Background
Copper catalysts are widely used in catalysis of various reactions, such as hydrogenation, hydrogenolysis, oxidation, reduction, and oxidative carbonylation, as substitutes for noble metal catalysts. The supported copper catalyst is used as a heterogeneous catalyst, is easy to separate and recover from a reaction system, and accords with the development concept of green chemistry. The traditional method for preparing the supported copper-based catalyst comprises an impregnation method, a coprecipitation method and the like. The impregnation method is used for preparing the corresponding supported copper-based catalyst by impregnating the carrier into the precursor solution, the operation is simple, and the catalyst generally has larger specific surface area and more dispersed metal particles. However, in the preparation of a catalyst by an impregnation method, the distribution state of the active component on the carrier is limited by various factors such as the concentration of the impregnation solution and the state of the carrier. Compared with an impregnation method, the coprecipitation method is easier to prepare the copper-based catalyst with good dispersity and uniformly distributed active components. However, the coprecipitation method has complicated operation steps and a long period, and the performance of the catalyst is affected by various factors, such as the pH value, the temperature, the type of the metal precursor, the aging time and the like during precipitation. Therefore, the development of a simple and controllable method for preparing the supported copper catalyst has important significance.
Disclosure of Invention
The invention aims to provide a copper-carbon composite catalyst and a preparation method thereof. Common copper salt is used as a copper source, amino acid is used as a carbon source, sodium chloride or potassium chloride is used as a template, and the copper-carbon composite catalyst is prepared by grinding, oxygen-free calcination and water washing. The copper nano-particles are uniformly loaded on the surface of the carbon substrate, the carbon substrate is flaky, the size is 0.5-5mm, the copper nano-particles are easy to filter and remove, the copper nano-particles are in a core-shell structure, the core is simple substance copper, the shell is one or the combination of simple substance copper, cuprous oxide, cupric hydroxide and cupric carbonate, the size is 100-500nm,
the preparation method comprises the following steps:
(1) weighing 1 part of amino acid and 0.1-1 part of copper salt according to the weight ratio, grinding and mixing uniformly;
(2) weighing 8 parts of salt, adding the salt into the materials, grinding and mixing uniformly;
(3) heating the materials to 800 ℃ in a nitrogen atmosphere, and preserving heat for 1 hour;
(4) and (5) cooling, washing with water to remove salt to obtain a finished product.
The amino acid in the step (1) is one or the combination of glutamic acid, glycine, alanine, leucine and aspartic acid;
the copper salt in the step (1) is one or the combination of copper chloride, copper nitrate and copper sulfate;
the salt in the step (2) is sodium chloride or potassium chloride.
The copper-carbon composite catalyst is applied to the preparation of p-aminophenol by reducing p-nitrophenol.
Compared with the prior art, the invention has the following advantages:
(1) the invention takes amino acid as a carbon source, and the amino acid is complexed with copper salt to play a role in dispersion, so that the copper nano particles with more uniformly dispersed particles are obtained.
(2) The copper nanoparticles are generated by reduction in the calcining process, are separated out from carbon, are loaded on the surface of the carbon, have good loading stability, are beneficial to the contact of a catalyst and a reaction substrate, and are easy to obtain better catalytic effect.
(3) By controlling the addition amount of the copper salt, the dispersion density of the copper nanoparticles on the surface of the carbon substrate can be adjusted.
(4) The method takes sodium chloride or potassium chloride as a template, prevents carbon from agglomerating in the calcining process, obtains the flaky carbon substrate with smaller particles and better dispersion, and is convenient for using the catalyst.
(5) In the washing process of the catalyst, the catalyst can be converted into forms of cuprous oxide, cupric hydroxide, cupric carbonate and the like from simple substance copper, and the catalyst with different forms can be obtained by controlling the washing process.
(6) The preparation of the catalyst uses common raw materials, is simple to operate, controllable and adjustable, and is easy for large-scale preparation.
(7) The copper-carbon composite catalyst is used for reducing p-nitrophenol, sodium borohydride is used as a reducing agent, the reaction can be completed within a few minutes at room temperature, the reaction speed is high, the energy consumption is low, the operation is simple and convenient, the equipment requirement is low, and the application prospect is good.
Drawings
FIG. 1 is an SEM micrograph of the catalyst obtained in example 1.
FIG. 2 is an SEM micrograph of the catalyst obtained in example 2.
FIG. 3 is an SEM micrograph of the catalyst obtained in example 3.
Detailed Description
Example 1:
weighing 1 g of copper chloride and 1 g of glutamic acid, grinding for 5 minutes, adding 8 g of sodium chloride, continuously grinding for 5 minutes, transferring into a muffle furnace, heating to 800 ℃ under nitrogen, preserving heat for 1 hour, cooling to room temperature, washing with water to remove salt, filtering, and drying in the air to obtain a catalyst, wherein diffraction peaks of simple substance copper, cuprous oxide, copper hydroxide and the like are detected by XRD.
Example 2:
weighing 0.5 g of copper nitrate and 1 g of alanine, grinding for 5 minutes, adding 8 g of sodium chloride, continuously grinding for 5 minutes, transferring into a muffle furnace, heating to 800 ℃ under nitrogen, preserving heat for 1 hour, cooling to room temperature, washing with water to remove salt, filtering and drying in the air to obtain the catalyst.
Example 3:
weighing 0.1 g of copper sulfate and 1 g of aspartic acid, grinding for 5 minutes, adding 8 g of potassium chloride, continuously grinding for 5 minutes, transferring into a muffle furnace, heating to 800 ℃ under nitrogen, preserving heat for 1 hour, cooling to room temperature, washing with water to remove salt, filtering and drying in the air to obtain the catalyst.
Example 4:
adding 3 ml of water, 3 mg of sodium borohydride and 20 microliters of 0.1 mol/l p-nitrophenol solution into a quartz cuvette, oscillating the solution to be light yellow green, standing for a long time for no reaction, adding a small amount of the catalyst obtained in example 2 (taking 10 microliters of solution prepared from 1 mg of catalyst and 3 milliliters of water), oscillating the solution for 2 minutes, and detecting by ultraviolet spectrum to find that the absorption peak at 400 nm completely disappears, which indicates that the nitro reduction reaction is complete.
Claims (2)
1. A copper-carbon composite catalyst and a preparation method thereof are characterized in that: the copper nano-particles are uniformly loaded on the surface of the carbon substrate, the carbon substrate is flaky, the size is 0.5-5mm, the copper nano-particles are easy to filter and remove, the copper nano-particles are in a core-shell structure, the core is simple substance copper, the shell is one or the combination of simple substance copper, cuprous oxide, cupric hydroxide and cupric carbonate, the size is 100-500nm,
the preparation method comprises the following preparation steps:
(1) weighing 1 part of amino acid and 0.1-1 part of copper salt according to the weight ratio, grinding and mixing uniformly;
(2) weighing 8 parts of salt, adding the salt into the materials, grinding and mixing uniformly;
(3) heating the materials to 800 ℃ in a nitrogen atmosphere, and preserving heat for 1 hour;
(4) and (5) cooling, washing with water to remove salt to obtain a finished product.
2. The copper-carbon composite catalyst and the preparation method thereof according to claim 1, wherein the copper-carbon composite catalyst comprises:
the amino acid in the step (1) is one or the combination of glutamic acid, glycine, alanine, leucine and aspartic acid;
the copper salt in the step (1) is one or the combination of copper chloride, copper nitrate and copper sulfate;
the salt in the step (2) is sodium chloride or potassium chloride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110376849.9A CN113181913A (en) | 2021-04-08 | 2021-04-08 | Copper-carbon composite catalyst and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110376849.9A CN113181913A (en) | 2021-04-08 | 2021-04-08 | Copper-carbon composite catalyst and preparation method thereof |
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| Publication Number | Publication Date |
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| CN113181913A true CN113181913A (en) | 2021-07-30 |
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| CN202110376849.9A Pending CN113181913A (en) | 2021-04-08 | 2021-04-08 | Copper-carbon composite catalyst and preparation method thereof |
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| JP2010150619A (en) * | 2008-12-26 | 2010-07-08 | Mitsui Mining & Smelting Co Ltd | Method for producing copper nanoparticle |
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