CN109876800A - A kind of preparation method of platinum/carbon nano-catalyst - Google Patents
A kind of preparation method of platinum/carbon nano-catalyst Download PDFInfo
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title claims abstract description 96
- 239000011943 nanocatalyst Substances 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 239000000243 solution Substances 0.000 claims abstract description 37
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 26
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 12
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 11
- 239000002243 precursor Substances 0.000 claims abstract description 11
- 239000000843 powder Substances 0.000 claims abstract description 10
- 238000005406 washing Methods 0.000 claims abstract description 8
- 229910017053 inorganic salt Inorganic materials 0.000 claims abstract description 3
- 239000012266 salt solution Substances 0.000 claims abstract description 3
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims description 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 18
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 14
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 10
- 239000000428 dust Substances 0.000 claims description 10
- 229910052700 potassium Inorganic materials 0.000 claims description 10
- 239000011591 potassium Substances 0.000 claims description 10
- 235000010333 potassium nitrate Nutrition 0.000 claims description 10
- 239000004323 potassium nitrate Substances 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical group COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 7
- 235000019253 formic acid Nutrition 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 6
- 239000008367 deionised water Substances 0.000 claims description 6
- 229910021641 deionized water Inorganic materials 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 6
- 238000001027 hydrothermal synthesis Methods 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 2
- 238000002604 ultrasonography Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 13
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- 230000000694 effects Effects 0.000 abstract description 3
- 239000002245 particle Substances 0.000 abstract description 2
- 238000001035 drying Methods 0.000 abstract 1
- 230000008570 general process Effects 0.000 abstract 1
- 231100000614 poison Toxicity 0.000 abstract 1
- 230000035484 reaction time Effects 0.000 abstract 1
- 239000003440 toxic substance Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 description 12
- 230000005540 biological transmission Effects 0.000 description 10
- 239000000446 fuel Substances 0.000 description 7
- 239000002105 nanoparticle Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 4
- 239000006229 carbon black Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 238000000053 physical method Methods 0.000 description 2
- 231100000572 poisoning Toxicity 0.000 description 2
- 230000000607 poisoning effect Effects 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 230000010757 Reduction Activity Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000000366 colloid method Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000003487 electrochemical reaction Methods 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 239000005431 greenhouse gas Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical group C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000000593 microemulsion method Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000002294 plasma sputter deposition Methods 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
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- Catalysts (AREA)
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Abstract
本发明所述的一种制备铂/碳纳米催化剂的制备方法，在室温条件下，调节反应器内铂前驱体溶液的PH值，再添加一定的无机盐溶液，并添碳粉，在超声波条件下，充分均匀分散，将反应器放置在水浴锅中，反应温度设定为在60~90℃下，添加还原剂反应1~3h，再进行洗涤、干燥，即得到铂/碳纳米催化剂粉体；本方法工艺简单通用、易操作、反应时间短且成本低廉，整个制备过程绿色环保，无毒性物质且不存在任何污染问题，最终得到铂颗粒均匀负载在碳的四周，分散性好，电催化活性高。
In the method for preparing platinum/carbon nano-catalyst according to the present invention, the pH value of the platinum precursor solution in the reactor is adjusted at room temperature, a certain inorganic salt solution is added, and carbon powder is added, and the pH value of the platinum precursor solution in the reactor is adjusted under ultrasonic conditions. The reaction temperature is set at 60~90℃, adding a reducing agent to react for 1~3h, and then washing and drying to obtain platinum/carbon nanocatalyst powder. The method has the advantages of simple and general process, easy operation, short reaction time and low cost, the whole preparation process is green and environmentally friendly, has no toxic substances and does not have any pollution problem, and finally obtains platinum particles uniformly supported around the carbon, with good dispersibility and electrocatalysis. High activity.
Description
Technical field
The present invention relates to a kind of preparation method of catalyst, especially a kind of preparation side for preparing platinum/carbon nano catalyst
Method belongs to catalyst preparation technical field.
Background technique
Mankind master's traditional fossil energy to be used at present occupies the ratio of the whole world consumption energy 80%, but fossil energy
A large amount of greenhouse gases CO2 and pollutant are generated in non-renewable and its use process in source, there have to ecological environment to be unfavorable
It influences.Fuel cell is a kind of power generation that chemical energy is changed into directly in a manner of electrochemical reaction electric energy without chemical combustion
Device.Wherein, operating temperature is low, starting is fast, energy because having for low-temperature fuel cell such as Proton Exchange Membrane Fuel Cells (PEMFC)
Measure high conversion rate the advantages that, be considered as field power station, electric car, portable power ideal source.In fuel cell
In, catalyst is the core material in battery.Mostly use noble metal platinum as catalyst in low-temperature fuel cell, i.e., with pallium-on-carbon
The catalyst that nano particle is reacted as anode and cathode, but durability is poor under PEMFC operating condition, in catalytic reaction process,
Be easy to appear: (1) platinum is not close in conjunction with carrier, falls off in the migration for leading to platinum；(2) poisoning and deactivation, fuel hydrogen
Gas is largely obtained by reformation hydrogen production, wherein can include a certain amount of CO, CO be easily adsorbed at the surface of platinum, causes platinum catalyst
Poisoning.And the expensive scarcity of resources of noble metal platinum, therefore the platinum catalyst of high activity is developed, the load capacity for reducing platinum obtains newly
Type high-performance, Low-cost electric catalyst are of great significance to the development for pushing fuel cell.
The preparation method of platinum/carbon nano catalyst is generally divided into chemical method and physical method.Different preparation methods and place
Manage bar part directly influences the properity of catalyst, and the partial size for the catalyst that different methods prepares, pattern is not
Together.Physical method is that thermal evaporation, the plasma sputtering etc. in the case where source metal is by vacuum condition are made nano particle and are supported on carbon black
On carrier.And chemical method is with metal ion or molecule for forerunner, complex or high molecular surfactant are formed for protective agent
Colloid；Or be supported on carrier under the limitation in carrier duct by thermal decomposition or electronation, obtain load type metal catalysis
Agent.Common chemical method has: infusion process, colloid method, electrochemical deposition method, ion-exchange, microemulsion method etc..
The preparation method of platinum/carbon nano catalyst is often complicated for operation in the prior art, target product low yield, Yi Zhongcao
The preparation method for making simple and high yield platinum/carbon nano catalyst urgently proposes.
Summary of the invention
To solve the above existing problem, the invention discloses a kind of preparation methods for preparing platinum/carbon nano catalyst, specifically
Steps are as follows:
(1) the platinum precursor solution prepared is placed in reactor, and adjusting solution ph at room temperature is 4 ~ 9, while preparing potassium nitrate
Solution is added dropwise in platinum precursor solution, is sufficiently mixed uniformly, according to the proportion of 0.1mg/mL ~ 2.5mg/ml and solution, adds
Add suitable carbon dust, is mixed 15 minutes under ultrasound condition, it is ensured that carbon dust is evenly dispersed in the solution；
(2) reactor is placed in water-bath, bath temperature is 60 ~ 90 DEG C, and reduction is added in the suspension obtained to step (1)
Agent, 1 ~ 3h of hydro-thermal reaction, then cooled to room temperature；
(3) washing product deionized water and dehydrated alcohol that step (2) obtains for several times is 7 to filtrate pH value, and filter residue is 70
DEG C dry 4 ~ 12h is to get arriving platinum/carbon nano catalyst powder.
Further, the concentration of step (1) the potassium chloroplatinate solution is 6.5mg/ml~10.5mg/ml.
Further, step (1) the inorganic salt solution solution is potassium nitrate, and the concentration of potassium nitrate is 0.5mg/ml
~5.5mg/ml.
Further, the step (1) carbon dust is commercially available VC-72R conductive black, and the proportion with solvent is
0.1mg/mL~2.5mg/ml。
Further, the step (1) adjusts pH value and uses commercially available potassium hydroxide (AR).
Further, the step (2) reducing agent is formic acid, and concentration is 5 ~ 10mol/L.
Beneficial effects of the present invention:
(1) present invention prepares raw material and is easy to get, and preparation process flow is simple, reaction can be completed under water solution system, without adding
Bonus point powder, reaction passes through after completing to be filtered, and product just can be obtained in washing, without centrifugation and is heat-treated, whole process pollution
It is small, it is high-efficient.
(2) for the present invention using catalyst is prepared under water bath condition, reaction condition is mild, is easy to get grain under the reaction temperature
The small Pt nanoparticle of diameter range, it is not easy to agglomeration occur, be added to inorganic salts and enter in platinum precursor solution solution, drop
The low reduction potential of platinum, using the available short grained nano platinum particle of formic acid, while it is stable to play auxiliary, and
Easily cleaning removes, and will not have a negative impact to catalyst activity.
Detailed description of the invention
Fig. 1 is the X ray diffracting spectrum that embodiment 1 prepares platinum/carbon nano catalyst；
Fig. 2 is that embodiment 1 prepares platinum/carbon nano catalyst transmission electron microscope picture；
Fig. 3 is that embodiment 1 prepares platinum/carbon nano catalyst transmission electron microscope picture；
Fig. 4 is the X ray diffracting spectrum that embodiment 2 prepares platinum/carbon nano catalyst
Fig. 5 is that embodiment 2 prepares platinum/carbon nano catalyst transmission electron microscope picture；
Fig. 6 embodiment 3 prepares platinum/carbon nano catalyst transmission electron microscope picture；
Fig. 7 is that embodiment 3 prepares platinum/carbon nano catalyst transmission electron microscope picture；
Fig. 8 is that embodiment 4 prepares platinum/carbon nano catalyst transmission electron microscope picture；
Fig. 9 is the linear scan figure that embodiment 4 prepares platinum/carbon nano catalyst.
Specific embodiment
Below by the drawings and specific embodiments, the invention will be further described, but is not to protect to the present invention
Protect the restriction of range.
Embodiment 1
A kind of preparation method of platinum/carbon nano catalyst, the specific steps are as follows:
(1) potassium chloroplatinate platinum solution 10ml, density 8.5mg/mL are prepared, is adjusted with potassium hydroxide by its PH to 7 or so；
(2) potassium nitrate solution concentration 1ml is prepared, density 2mg/mL is added dropwise in potassium chloroplatinate solution, is sufficiently stirred mixed
It closes, then adds the XC-72R conductive black of 2mg, be placed into ultrasonic instrument, ultrasonic 30min, it is ensured that XC-72R conduction charcoal
It is black fully dispersed in precursor solution；
(3) preparing 10ml formic acid concn is 5mol/L as reducing agent, and reaction vessel is put into water-bath, is obtained to step (2)
To suspension in reducing agent is added, in 70 DEG C of 1 ~ 3h of hydro-thermal reaction, then cooled to room temperature；
(4) washing product deionized water and dehydrated alcohol that step (3) obtains for several times is 7 to filtrate pH value, and filter residue is 70
DEG C dry 4 ~ 12h is to get arriving platinum/carbon nano catalyst powder.
Fig. 1 is the XRD diagram of platinum/carbon nano catalyst powder that the present embodiment is prepared, as we know from the figure product be platinum/
Carbon nanocatalyst, Fig. 2 and Fig. 3 are the transmission electron microscope picture for the platinum/carbon nano catalyst that the present embodiment is prepared, the institute from figure
The Pt nanoparticle size prepared is uniformly dispersed on carbon dust within the scope of 4 ~ 5nm.
Embodiment 2
A kind of preparation method of platinum/carbon nano catalyst, the specific steps are as follows:
(1) potassium chloroplatinate platinum solution 12ml, density 6.5mg/mL are prepared, is adjusted with potassium hydroxide by its PH to 6 or so；
(2) potassium nitrate solution concentration 2ml is prepared, density 2.5mg/mL is added dropwise in potassium chloroplatinate solution, is sufficiently stirred
Then mixing is added the XC-72R conductive black of 1.4mg, is placed into ultrasonic instrument, ultrasonic 30min, it is ensured that XC-72R is led
Electric carbon black is fully dispersed in precursor solution；
(3) preparing 12ml formic acid concn is 6mol/L as reducing agent, and reaction vessel is put into water-bath, is obtained to step (2)
To suspension in reducing agent is added, in 60 DEG C of 1 ~ 3h of hydro-thermal reaction, then cooled to room temperature；
(4) washing product deionized water and dehydrated alcohol that step (3) obtains for several times is 7 to filtrate pH value, and filter residue is 70
DEG C dry 4 ~ 12h is to get arriving platinum/carbon nano catalyst powder.
Fig. 4 is the XRD diagram of platinum/carbon nano catalyst powder that the present embodiment is prepared, as we know from the figure product be platinum/
Carbon nanocatalyst, Fig. 5 is the transmission electron microscope picture for the platinum/carbon nano catalyst that the present embodiment is prepared, prepared from figure
Pt nanoparticle size out is uniformly dispersed on carbon dust within the scope of 4 ~ 5nm.
Embodiment 3
A kind of preparation method of platinum/carbon nano catalyst, the specific steps are as follows:
(1) potassium chloroplatinate platinum solution 15ml, density 7mg/mL are prepared, is adjusted with potassium hydroxide by its PH to 8 or so；
(2) potassium nitrate solution concentration 3ml is prepared, density 3.5mg/mL is added dropwise in potassium chloroplatinate solution, is sufficiently stirred
Then mixing is added the XC-72R conductive black of 9mg, is placed into ultrasonic instrument, ultrasonic 30min, it is ensured that XC-72R is conductive
Carbon black is fully dispersed in precursor solution；
(3) preparing 15ml formic acid concn is 5mol/L as reducing agent, and reaction vessel is put into water-bath, is obtained to step (2)
To suspension in reducing agent is added, in 65 DEG C of 1 ~ 3h of hydro-thermal reaction, then cooled to room temperature；
(4) washing product deionized water and dehydrated alcohol that step (3) obtains for several times is 7 to filtrate pH value, and filter residue is 70
DEG C dry 4 ~ 12h is to get arriving platinum/carbon nano catalyst powder.
Fig. 6 and Fig. 7 is the transmission electron microscope picture for the platinum/carbon nano catalyst that the present embodiment is prepared, prepared from figure
Pt nanoparticle size out is uniformly dispersed on carbon dust within the scope of 4 ~ 5nm.
Embodiment 4
A kind of preparation method of platinum/carbon nano catalyst of this example, the specific steps are as follows:
(1) potassium chloroplatinate platinum solution 8ml, density 6mg/mL are prepared, is adjusted with potassium hydroxide by its PH to 5 or so；
(2) potassium nitrate solution concentration 1ml is prepared, density 0.5mg/mL is added dropwise in potassium chloroplatinate solution, is sufficiently stirred
Then mixing is added the XC-72R conductive black of 0.8mg, is placed into ultrasonic instrument, ultrasonic 30min, it is ensured that XC-72R is led
Electric carbon black is fully dispersed in precursor solution；
(3) preparing 8ml formic acid concn is 6mol/L as reducing agent, and reaction vessel is put into water-bath, is obtained to step (2)
Suspension in reducing agent is added, in 80 DEG C of 1 ~ 3h of hydro-thermal reaction, then cooled to room temperature；
(4) washing product deionized water and dehydrated alcohol that step (3) obtains for several times is 7 to filtrate pH value, and filter residue is 70
DEG C dry 4 ~ 12h is to get arriving platinum/carbon nano catalyst powder.
Fig. 8 is the transmission electron microscope picture for the platinum/carbon nano catalyst that the present embodiment is prepared, the prepared platinum from figure
Nano particle size is uniformly dispersed on carbon dust within the scope of 4 ~ 5nm.Fig. 9 is the linear electricity for testing catalytic oxygen reduction activity
Bit scan figure is compared with the business platinum electrode of platinum containing amount 20%, and catalytic performance is better than business platinum electrode.Above-mentioned specific reality
Applying mode is only to clearly illustrate example of the present invention, and not limit the embodiments.For fields
Those of ordinary skill for, other different forms of changes or modifications may be made based on the above description, here
There is no need to be exhaustive to all embodiments, and thus changes and variations that derived from still in
In protection scope of the present invention.
Claims (6)
1. a kind of preparation method for preparing platinum/carbon nano catalyst, which is characterized in that specific step is as follows:
(1) the platinum precursor solution prepared is placed in reactor, and adjusting solution ph at room temperature is 4 ~ 9, while preparing potassium nitrate
Solution is added dropwise in platinum precursor solution, is sufficiently mixed uniformly, according to the proportion of 0.1mg/mL ~ 2.5mg/ml and solution, adds
Add suitable carbon dust, is mixed 15 minutes under ultrasound condition, it is ensured that carbon dust is evenly dispersed in the solution；
(2) reactor is placed in water-bath, bath temperature is 60 ~ 90 DEG C, and reduction is added in the suspension obtained to step (1)
Agent, 1 ~ 3h of hydro-thermal reaction, then cooled to room temperature；
(3) washing product deionized water and dehydrated alcohol that step (2) obtains for several times is 7 to filtrate pH value, and filter residue is 70
DEG C dry 4 ~ 12h is to get arriving platinum/carbon nano catalyst powder.
2. a kind of preparation method for preparing platinum/carbon nano catalyst according to claim 1, which is characterized in that the step
Suddenly the concentration of potassium chloroplatinate solution described in (1) is 6.5mg/ml~10.5mg/ml.
3. a kind of preparation method for preparing platinum/carbon nano catalyst according to claim 1, which is characterized in that the step
Suddenly (1) described inorganic salt solution solution is potassium nitrate, and the concentration of potassium nitrate is 0.5mg/ml~5.5mg/ml.
4. a kind of preparation method for preparing platinum/carbon nano catalyst according to claim 1, which is characterized in that the step
Suddenly (1) described carbon dust is commercially available VC-72R conductive black, and the proportion with solvent is 0.1mg/mL ~ 2.5mg/ml.
5. a kind of preparation method for preparing platinum/carbon nano catalyst according to claim 1, which is characterized in that the step
Suddenly (1) adjusts pH value and uses commercially available potassium hydroxide (AR).
6. a kind of preparation method for preparing platinum/carbon nano catalyst according to claim 1, which is characterized in that the step
Suddenly (2) described reducing agent is formic acid, and concentration is 5 ~ 10mol/L.
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| CN111111690A (en) * | 2019-12-27 | 2020-05-08 | 大连理工大学 | A carbon-supported platinum-cobalt-rhodium nanorod catalyst for acid hydrogen evolution reaction and its preparation method and application |
| CN111939897A (en) * | 2020-08-26 | 2020-11-17 | 上海交通大学 | A kind of platinum nanowire particle catalyst preparation method |
| CN114914463A (en) * | 2021-02-08 | 2022-08-16 | 中国科学院大连化学物理研究所 | High-load high-dispersion platinum-carbon catalyst and preparation method of amino ligand thereof |
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