CN115106083A - Amorphous Cu 2 In-situ synthesis method and application of O/biomass carbon catalyst - Google Patents
Amorphous Cu 2 In-situ synthesis method and application of O/biomass carbon catalyst Download PDFInfo
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- CN115106083A CN115106083A CN202210749704.3A CN202210749704A CN115106083A CN 115106083 A CN115106083 A CN 115106083A CN 202210749704 A CN202210749704 A CN 202210749704A CN 115106083 A CN115106083 A CN 115106083A
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- 239000002028 Biomass Substances 0.000 title claims abstract description 54
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims abstract description 53
- 229910052799 carbon Inorganic materials 0.000 title claims abstract description 45
- 239000003054 catalyst Substances 0.000 title claims abstract description 42
- 238000011065 in-situ storage Methods 0.000 title claims abstract description 18
- 238000001308 synthesis method Methods 0.000 title claims abstract description 10
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000006185 dispersion Substances 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 11
- 238000000227 grinding Methods 0.000 claims abstract description 10
- 238000005406 washing Methods 0.000 claims abstract description 7
- 239000007790 solid phase Substances 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 5
- 235000009025 Carya illinoensis Nutrition 0.000 claims abstract description 4
- 241001453450 Carya illinoinensis Species 0.000 claims abstract description 4
- 239000012299 nitrogen atmosphere Substances 0.000 claims abstract description 4
- 238000012216 screening Methods 0.000 claims abstract description 4
- 229910021642 ultra pure water Inorganic materials 0.000 claims abstract description 4
- 239000012498 ultrapure water Substances 0.000 claims abstract description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract description 3
- 239000010949 copper Substances 0.000 claims description 51
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 241000723418 Carya Species 0.000 claims description 8
- 239000002245 particle Substances 0.000 claims description 8
- 238000006722 reduction reaction Methods 0.000 claims description 7
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 5
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- 239000012279 sodium borohydride Substances 0.000 claims description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 5
- 239000002351 wastewater Substances 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 239000000843 powder Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 238000007605 air drying Methods 0.000 claims description 2
- 238000005119 centrifugation Methods 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 abstract description 6
- 239000006227 byproduct Substances 0.000 abstract description 2
- 239000012084 conversion product Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 8
- 229910000510 noble metal Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 241000899834 Obovaria olivaria Species 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 229910002703 Al K Inorganic materials 0.000 description 1
- 238000000026 X-ray photoelectron spectrum Methods 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 1
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000007146 photocatalysis Methods 0.000 description 1
- 230000001699 photocatalysis Effects 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 239000002910 solid waste Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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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
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/18—Carbon
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/16—Reducing
-
- 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
Abstract
The invention discloses amorphous Cu 2 An in-situ synthesis method and application of an O/biomass carbon catalyst; the in-situ generation method comprises the following steps: firstly, grinding the pecan shells, washing, drying, grinding and screening to obtain the biomass carbon. Secondly, burning the biomass carbon in a nitrogen atmosphere to obtain biomass carbon powder; thirdly, adding the biomass carbon powder obtained in the second step into ultrapure water; oxygen gas was continuously introduced into the resulting dispersion, and Cu (NO) was added dropwise 3 ) 2 Solution and NaBH 4 Solution of Cu 2+ Reduction ofTo Cu 2 O and making it supported on biomass carbon. Thereafter, the solid phase in the dispersion was separated to obtain a catalyst. Amorphous Cu prepared by the invention 2 The O/biomass carbon catalyst has excellent catalytic activity and extremely high selectivity, more than 90 percent of PNP can be degraded within 5 minutes, and the conversion products are all p-aminophenol, no other by-products are generated, and no secondary pollution is generated.
Description
Technical Field
The invention relates to an in-situ synthesis method of amorphous Cu 2 A method for preparing an O/biomass carbon catalyst and application thereof.
Background
P-nitrophenol (PNP) and derivatives thereof are typical aromatic pollutants discharged by industries such as pesticides, fuels, herbicides and the like. The disposal of such contaminants presents a challenge to researchers in the field of nitroaromatics, the nitrophenols of which are generally highly toxic and carcinogenic. Para-aminophenol (PAP) obtained by reduction of PNP is a very useful organic chemical raw material intermediate used in the industries of dye, pharmacy, photosensitive material, antioxidant and the like, and PAP is far less toxic than PNP.
Over the past several decades, efforts have been made to remove PNP from wastewater by methods commonly used including chemical reduction, solid phase extraction, photocatalysis, and Fenton oxidation. In the prior art, NaBH is used 4 The reduction of PNP to harmless para-aminophenol (PAP) as a reducing agent has received much attention due to its simplicity of operation, high conversion efficiency and great industrial relevance. Many noble metals such as Ag, Ru, Au, Pd are widely used as catalysts for this reaction. However, the difficult availability and high cost of precious metals have limited their practical engineering applications. Researchers have therefore focused on the exploration of non-noble metal catalysts to reduce costs. However, the catalytic performance and stability of non-noble metals are difficult to achieve. To date, a green, highly efficient NaBH has been sought that can be applied in large-scale engineering 4 Reduction of catalysts for PNP degradation reactions remains a significant challenge.
Disclosure of Invention
In view of the above technical problems in the prior art, the present invention aims to provide an in-situ synthesis method of amorphous Cu 2 An O/biomass carbon catalyst, a preparation method and application thereof.
In a first aspect, the present invention provides an amorphous Cu 2 O/biochar catalyst by in-situ generation of Cu in a dispersion containing biochar 2 O, to Cu 2 O is loaded on biomass carbon. In situ generation of Cu 2 The mode of O is as follows: in the presence of biomass carbonReducing copper nitrate in the dispersion with sodium borohydride to obtain Cu 2 O。
Preferably, the sodium borohydride solution and the copper nitrate solution are added dropwise to the biomass carbon-containing dispersion system while maintaining the aeration of oxygen, so that the Cu generated in situ 2 The O is uniformly loaded on the biomass carbon.
Preferably, the biomass carbon is obtained by grinding pecan shells into powder.
The amorphous Cu 2 The in-situ generation method of the O/biomass carbon catalyst comprises the following steps:
step one, grinding the hickory shells into hickory particles, and washing, drying, grinding and screening the obtained hickory particles to obtain the biomass carbon with the particle size of more than 100 meshes.
Step two, burning the biomass carbon obtained in the step one in a nitrogen atmosphere to obtain biomass carbon powder;
step three, adding the biomass carbon powder obtained in the step two into ultrapure water; oxygen was continuously introduced into the resulting dispersion, and Cu (NO3) was added dropwise 2 Solution and NaBH 4 Solution of Cu 2+ Reduction to Cu 2 O and making it supported on biomass carbon. Thereafter, the solid phase in the dispersion is separated to obtain amorphous Cu 2 O/Biomass carbon catalyst.
Preferably, in the second step, the flow rate of nitrogen is 4 mol/h.
Preferably, in the second step, the burning temperature is 250 ℃.
Preferably, in step three, the solid phase in the dispersion is separated by centrifugation, followed by washing and air drying.
Preferably, in the third step, the reaction temperature is 10-50 ℃.
Preferably, in step three, the Cu (NO) is 3 ) 2 The solution concentration is 0.2 mmol.L -1 ；NaBH 4 The solution concentration is 26 mmol.L -1 。
In a second aspect, the present invention provides the aforementioned amorphous Cu 2 The application of the O/biomass carbon catalyst in catalytic reduction of p-nitrophenol in wastewater.
Preferably, a hydrogen-containing reducing agent is added in the process of catalytic reduction of the p-nitrophenol, so that the p-nitrophenol generates the p-aminophenol.
Preferably, the hydrogen-containing reducing agent is sodium borohydride.
Preferably, the reaction temperature for catalytic reduction of p-nitrophenol is 25 ℃.
Compared with the prior art, the invention has the following beneficial effects:
1. amorphous Cu prepared by the invention 2 The O/biomass carbon catalyst has excellent catalytic activity and extremely high selectivity, more than 90 percent of PNP can be degraded within 5 minutes, and the conversion products are all p-aminophenol, no other by-products are generated, and no secondary pollution is generated.
2. The catalyst provided by the invention adopts Cu to replace a common noble metal raw material, has simple application conditions, has no special requirements on reaction equipment, and can be used for catalytically reducing PNP at normal temperature and normal pressure. Greatly reducing the treatment cost of the PNP wastewater.
3. The method takes the waste pecan shells as the raw material, and adopts an environment-friendly method to synthesize the amorphous Cu 2 The O/biomass carbon catalyst realizes the resource utilization of the solid waste.
Drawings
FIG. 1 is a diagram showing the effect of the catalyst prepared by the present invention on the catalytic degradation of PNP;
FIG. 2 is an X-ray photoelectron spectrum of the catalyst prepared by the present invention;
FIG. 3 is an X-ray diffraction pattern of the catalyst prepared by the present invention.
Detailed Description
The present invention is further illustrated by the following examples, which should not be construed as limiting the scope of the invention.
Amorphous Cu 2 The in-situ synthesis method of the O/biomass carbon catalyst comprises the following steps:
grinding waste hickory shells into hickory particles; and then washing the obtained hickory nut particles with purified water, naturally drying, grinding and screening to obtain the hickory nut powder with the granularity of more than 100 meshes. The obtained hickory nut powder is biomass carbon.
Step two, burning the biomass carbon obtained in the step one in a nitrogen atmosphere to obtain biomass carbon powder;
step three, adding the prepared biomass carbon powder into a customization device filled with ultrapure water; then, oxygen gas was continuously introduced into the obtained dispersion, and 0.2 mmol. multidot.L was continuously added dropwise thereto -1 Cu (NO3) 2 Solution and 26 mmol. L -1 NaBH of 4 A solution; the whole process is carried out under the condition of 30 ℃ water bath. Centrifuging the reacted dispersion system, washing the obtained solid phase with ethanol, and naturally drying to obtain amorphous Cu 2 O/Biomass carbon catalyst.
Subjecting the obtained amorphous Cu 2 The O/biomass carbon catalyst is applied to the catalytic degradation of waste water containing PNP, and the process is as follows:
in a 100mL beaker 54mL of PNP and freshly prepared NaBH were added 4 Mixed solution of (3) (NaBH) 4 Has a molar concentration of 26 mmol. L -1 The molar concentration of PNP is 0.13 mmol.L -1 ) Placing the beaker in a constant temperature water bath at 30 ℃, and then adding 0.1g of amorphous Cu 2 And (3) continuously stirring the O/biomass carbon catalyst in the reaction process. Samples were taken from the beaker every 1 minute and the PNP concentration in the sample was measured using an ultraviolet spectrophotometer. The results are shown in FIG. 1. As can be seen from fig. 1, the PNP concentration rapidly decreased after the addition of the catalyst prepared in this example, and the PNP was completely degraded after 5 minutes of reaction. And a product peak appears only at the absorption wavelength (300nm) corresponding to the PNP in the reaction process, which shows that the catalyst prepared by the embodiment has extremely high selectivity.
Amorphous Cu obtained by the preparation method 2 The chemical composition of the O/biochar catalyst was analyzed by X-ray photoelectron spectroscopy (XPS, Thermo Scientific K-Alpha) using an Al K α X-ray source (h ν 1486.6 eV). The results are shown in FIG. 2. As can be seen from the figure, the catalyst prepared in the example has two obvious peaks at binding energies of 931.6eV and 951.8eV, which correspond to Cu 2p1/2 and Cu 2p3/2, respectively, and the O1s spectrum in the figure shows thatThe product has only one O peak, appears at 532.4eV, and the energy spectrums of Cu 2p and O1s indicate that the only existence form of Cu in the catalyst is Cu 2 O, which shows that the preparation method provided in this example can make full use of raw materials and obtain a catalyst with high catalytic efficiency.
Amorphous Cu obtained by the preparation method 2 The structure of the O/biochar catalyst was measured by X-ray diffraction (XRD, Rigaku Ultima IV)). The results are shown in FIG. 3. It can be seen from the figure that the catalyst does not produce a distinct absorption peak corresponding to Cu, which indicates that the catalyst produces an amorphous Cu 2 And O. Amorphous Cu2O is more prone to defect sites, and most of these generated defect sites are active sites for catalytic reactions.
Claims (10)
1. Amorphous Cu 2 The in-situ synthesis method of the O/biomass carbon catalyst is characterized by comprising the following steps: firstly, grinding the hickory shells into hickory particles, and washing, drying, grinding and screening the obtained hickory particles to obtain biomass carbon with the particle size of more than 100 meshes;
step two, burning the biomass carbon obtained in the step one in a nitrogen atmosphere to obtain biomass carbon powder;
step three, adding the biomass carbon powder obtained in the step two into ultrapure water; oxygen gas was continuously introduced into the resulting dispersion, and Cu (NO) was added dropwise 3 ) 2 Solution and NaBH 4 Solution of Cu 2+ Reduction to Cu 2 O and causing it to be supported on biomass carbon; thereafter, the solid phase in the dispersion is separated to obtain amorphous Cu 2 O/Biomass carbon catalyst.
2. An amorphous Cu according to claim 1 2 The in-situ synthesis method of the O/biomass carbon catalyst is characterized by comprising the following steps: in the second step, the flow rate of nitrogen is 4mol/h, and the ignition temperature is 250 ℃.
3. An amorphous Cu according to claim 1 2 The in-situ synthesis method of the O/biomass carbon catalyst is characterized in thatThe method comprises the following steps: in the third step, the solid phase in the dispersion is separated by means of centrifugation, washing and air drying.
4. An amorphous Cu according to claim 1 2 The in-situ synthesis method of the O/biomass carbon catalyst is characterized by comprising the following steps: in step three, the Cu (NO) is 3 ) 2 The solution concentration is 0.2 mmol.L -1 ；NaBH 4 The solution concentration is 26 mmol.L -1 (ii) a The reaction temperature is 10-50 ℃.
5. Amorphous Cu 2 The O/biomass carbon catalyst is characterized in that: by in-situ generation of Cu in dispersions containing biomass carbon 2 O, to Cu 2 O is obtained in a manner of loading on biomass carbon; in situ generation of Cu 2 The mode of O is as follows: reduction of copper nitrate using sodium borohydride in a biomass carbon containing dispersion to obtain Cu 2 O。
6. An amorphous Cu according to claim 5 2 The O/biomass carbon catalyst is characterized in that: simultaneously dropwise adding the sodium borohydride solution and the copper nitrate solution into a dispersion system containing biomass carbon under the condition of keeping oxygen introduction, so that Cu generated in situ 2 The O is uniformly loaded on the biomass carbon.
7. An amorphous Cu according to claim 5 2 The O/biomass carbon catalyst is characterized in that: the biomass carbon is obtained by grinding pecan shells into powder.
8. An amorphous Cu as claimed in any one of claims 5 to 7 2 The application of the O/biomass carbon catalyst in catalytic reduction of p-nitrophenol in wastewater.
9. Use according to claim 8, characterized in that: adding a hydrogen-containing reducing agent in the process of catalytically reducing the p-nitrophenol to enable the p-nitrophenol to generate the p-aminophenol.
10. Use according to claim 8, characterized in that: the reaction temperature for catalytic reduction of p-nitrophenol is 25 ℃.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102423688A (en) * | 2011-08-26 | 2012-04-25 | 昆明理工大学 | Preparation method for walnut shell active carbon adsorbent for purifying low concentration phosphine |
| CN104772146A (en) * | 2015-03-18 | 2015-07-15 | 昆明理工大学 | Preparation method of modified bio-charcoal based catalyst |
| CN111167406A (en) * | 2020-01-13 | 2020-05-19 | 农业农村部环境保护科研监测所 | La (OH)3Preparation method of nanorod/walnut shell biochar composite material |
| CN112694411A (en) * | 2020-12-29 | 2021-04-23 | 浙江工业大学 | Simple method for preparing p-aminophenol by reducing p-nitrophenol |
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- 2022-06-28 CN CN202210749704.3A patent/CN115106083A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102423688A (en) * | 2011-08-26 | 2012-04-25 | 昆明理工大学 | Preparation method for walnut shell active carbon adsorbent for purifying low concentration phosphine |
| CN104772146A (en) * | 2015-03-18 | 2015-07-15 | 昆明理工大学 | Preparation method of modified bio-charcoal based catalyst |
| CN111167406A (en) * | 2020-01-13 | 2020-05-19 | 农业农村部环境保护科研监测所 | La (OH)3Preparation method of nanorod/walnut shell biochar composite material |
| CN112694411A (en) * | 2020-12-29 | 2021-04-23 | 浙江工业大学 | Simple method for preparing p-aminophenol by reducing p-nitrophenol |
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