CN105964247B - A kind of preparation method of three-dimensional redox graphene load nano Pd particle hydrogenation catalyst - Google Patents
A kind of preparation method of three-dimensional redox graphene load nano Pd particle hydrogenation catalyst Download PDFInfo
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 239000003054 catalyst Substances 0.000 title claims abstract description 35
- 229910021389 graphene Inorganic materials 0.000 title claims abstract description 23
- 239000002245 particle Substances 0.000 title claims abstract description 15
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 101150003085 Pdcl gene Proteins 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 9
- 238000001027 hydrothermal synthesis Methods 0.000 claims abstract description 6
- 239000007864 aqueous solution Substances 0.000 claims abstract description 3
- 239000000243 solution Substances 0.000 claims description 27
- 238000002604 ultrasonography Methods 0.000 claims description 16
- 229910002804 graphite Inorganic materials 0.000 claims description 13
- 239000010439 graphite Substances 0.000 claims description 13
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000008367 deionised water Substances 0.000 claims description 10
- 229910021641 deionized water Inorganic materials 0.000 claims description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- GDSOZVZXVXTJMI-SNAWJCMRSA-N (e)-1-methylbut-1-ene-1,2,4-tricarboxylic acid Chemical compound OC(=O)C(/C)=C(C(O)=O)\CCC(O)=O GDSOZVZXVXTJMI-SNAWJCMRSA-N 0.000 claims 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 abstract description 22
- 229960005070 ascorbic acid Drugs 0.000 abstract description 11
- 235000010323 ascorbic acid Nutrition 0.000 abstract description 11
- 239000011668 ascorbic acid Substances 0.000 abstract description 11
- 230000003197 catalytic effect Effects 0.000 abstract description 7
- 238000011084 recovery Methods 0.000 abstract description 6
- 239000006185 dispersion Substances 0.000 abstract description 5
- 150000001336 alkenes Chemical class 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 230000008021 deposition Effects 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000002243 precursor Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 26
- 239000008236 heating water Substances 0.000 description 8
- 238000001291 vacuum drying Methods 0.000 description 7
- 239000002105 nanoparticle Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 241000446313 Lamella Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
- 229910002666 PdCl2 Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002082 metal nanoparticle Substances 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- -1 oxidation Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 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
- 239000002904 solvent Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
Classifications
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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
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of preparation method of three-dimensional redox graphene load nano Pd particle hydrogenation catalyst, a certain amount of PdCl is added into its aqueous solution using graphene oxide as support precursor for this method2And ascorbic acid, make Pd uniform deposition on the three-dimensional redox graphene of formation by one step hydro thermal method, so that the loading type nano Pd particle of high degree of dispersion be made.Above-mentioned catalyst is used for the hydrogenation reaction of alkene, there is very high catalytic activity and stability, and the rate of recovery with higher.The catalyst preparation conditions are mild, process is simple, low in cost, it is easy to accomplish industrialized production.
Description
Technical field
The present invention relates to noble metal hydrogenation catalyst and its preparation technical field, in particular to a kind of three-dimensional oxygen reduction fossil
The preparation method of black alkene load nano Pd particle hydrogenation catalyst.
Background technique
Hydrogenation reaction is one of reaction important in Industrial Catalysis.Catalyst currently used for the reaction is mainly Pd, Pt
Equal noble metals.Metallic catalyst, especially nano Pd particle, because its excellent catalytic activity and selectivity are in heterogeneous catalysis field
In occupy an important position.Nano Pd particle is easy to reunite, be difficult to be stabilized and difficult recycling is the problem currently encountered, and research
Hot spot.By support dispersion nano Pd particle, the reunion of nanoparticle is prevented by the active force of carrier and Pd, increases its rate of recovery
It is more effective mode.The carrier studied at present mainly has: Al2O3、SiO2, active carbon, molecular sieve etc..But the presence of carrier
It will affect the diffusion of reactants and products again, reduce reaction rate.Therefore, to give full play to the unique catalytic of nano Pd particle
Can, not only to guarantee being stabilized for the Pd of high dispersive, while suitable carrier also to be selected to be conducive to the progress reacted.
Graphene, alternatively referred to as " mono-layer graphite ", be by single layer of carbon atom it is tightly packed at bi-dimensional cellular shape crystal, tool
Have compared with electric-conductivity heat-conductivity high, big specific surface area and splendid thermal stability, becomes the excellent carrier of nano metal.Currently, with
Graphene is carrier, and researchers have prepared various metals nanoparticle (Pt, Au, Pd, Ag, Fe etc.), and in Suzuki idol
Excellent catalytic activity is shown in the reaction such as connection plus hydrogen, oxidation, water decomposition.But graphene is often because mutual by π-π
It acts on and reunites, accumulates, specific surface area is caused to reduce, resistance increases, and performance is greatly reduced, to limit its application.Three-dimensional stone
The appearance of black alkene not only solves the above problem, also as its is light, volume is easy to control, easy processing and good mechanical performance etc.
It is concerned.And compared with conventional two-dimensional graphene carrier, three-dimensional lamella porous structure can avoid graphene sheet layer and repeat heap
Pile is more advantageous to the dispersion of metal nanoparticle, and has the very high rate of recovery.Therefore, easy to operate, environment friend is selected
Good, low-cost method prepares three-dimensional redox graphene carried metal nano Pd particle and has a good application prospect.
Summary of the invention
The technical problem to be solved by the present invention is to easily cause lamella stacking for two-dimensional graphene load Pd nanoparticle, return
The problems such as utilization rate is low is received, provides a kind of relatively easy, cleaning, high-dispersion Pd nanoparticle/three-dimensional that prepare of low cost restores
The method of graphene oxide hydrogenation catalyst.
The technical solution adopted by the present invention to solve the technical problems is:
A kind of preparation method of three-dimensional redox graphene load nano Pd particle hydrogenation catalyst, which is with three-dimensional
Redox graphene is carrier, using nano Pd particle as active component, is obtained using one step hydro thermal method.The specific steps of this method are such as
Under:
It weighs a certain amount of graphite oxide to be added into deionized water, graphite oxide concentration is 0.5-4mg/mL, then in room
The lower ultrasound of temperature, obtains the graphene oxide solution of high degree of dispersion；The 0.02mol/L of 0.3-1mL is added into resulting solution
PdCl2The ascorbic acid of aqueous solution and 60-100mg handles the solution under certain ultrasound condition, will be molten after ultrasound
Liquid hydro-thermal process under certain condition, acquired solution is centrifugated, is washed with deionized, and vacuum drying is to get to described
Catalyst.
As limitation of the invention, certain ultrasound condition of the present invention are as follows: supersonic frequency 120-240W, time
5-20min；The hydrothermal condition is: 60-90 DEG C of temperature, time 0.5-2h.
It finds under study for action, in the case where being added without any crosslinking agent and high temperature and pressure, by one step hydro thermal method energy
Enough realize the formation of the three-dimensional redox graphene of Pd load, and Pd nanoparticle can be highly dispersed in three-dimensional reduction-oxidation
The surface of graphene.
This method avoid the complex steps that traditional first synthesis three-dimensional grapheme loads Pd by chemical reduction method again, borrow
It helps the reduction of ascorbic acid that can promote the formation of three-dimensional grapheme but also realizes the deposition of Pd particle simultaneously.
Further, since carrier is three-dimensional redox graphene, so that the catalyst prepared by us is in subsequent reaction
There is the fabulous rate of recovery in system.
The synthetic method step is simple, mild condition and low in cost, easy to industrialized production.
Catalyst of the present invention shows good catalytic activity and reusability in the hydrogenation reaction of alkene.
Specific embodiment
The present invention will be described further with regard to following embodiment, however, it should be noted that these embodiments are only to illustrate
It is used, and is not necessarily to be construed as the limitation that the present invention is implemented.
Embodiment 1
It weighs 0.04g graphite oxide to be added in 80mL deionized water, be ultrasonically treated, supersonic frequency 180W, room temperature
After ultrasonic, the PdCl of the 0.02mol/L of 0.5mL is added into solution by ultrasonic 1.5h2The ascorbic acid of solution and 80mg,
The ultrasound 5min at 180W, 90 DEG C of reaction 1.5h of heating water bath, is centrifugated after reaction, is washed with deionized 5 times, and 50
DEG C vacuum drying 2h, obtains the catalyst A.
Embodiment 2
It weighs 0.04g graphite oxide to be added in 40mL deionized water, be ultrasonically treated, supersonic frequency 180W, room temperature
After ultrasonic, the PdCl of the 0.02mol/L of 0.5mL is added into solution by ultrasonic 1.5h2The ascorbic acid of solution and 60mg,
The ultrasound 5min at 180W, 90 DEG C of reaction 1.5h of heating water bath, is centrifugated after reaction, is washed with deionized 5 times, and 50
DEG C vacuum drying 2h, obtains the catalyst B.
Embodiment 3
It weighs 0.04g graphite oxide to be added in 20mL deionized water, be ultrasonically treated, supersonic frequency 180W, room temperature
After ultrasonic, the PdCl of the 0.02mol/L of 0.5mL is added into solution by ultrasonic 1.5h2The ascorbic acid of solution and 80mg,
The ultrasound 5min at 180W, 90 DEG C of reaction 1.5h of heating water bath, is centrifugated after reaction, is washed with deionized 5 times, and 50
DEG C vacuum drying 2h, obtains the catalyst C.
Embodiment 4
It weighs 0.04g graphite oxide to be added in 10mL deionized water, be ultrasonically treated, supersonic frequency 180W, room temperature
After ultrasonic, the PdCl of the 0.02mol/L of 0.3mL is added into solution by ultrasonic 1.5h2The ascorbic acid of solution and 80mg,
The ultrasound 5min at 180W, 90 DEG C of reaction 1.5h of heating water bath, is centrifugated after reaction, is washed with deionized 5 times, and 50
DEG C vacuum drying 2h, obtains the catalyst D.
Embodiment 5
It weighs 0.04g graphite oxide to be added in 20mL deionized water, be ultrasonically treated, supersonic frequency 180W, room temperature
After ultrasonic, the PdCl of the 0.02mol/L of 1mL is added into solution by ultrasonic 1.5h2The ascorbic acid of solution and 80mg,
Ultrasound 5min under 180W, 90 DEG C of reaction 1.5h of heating water bath, is centrifugated after reaction, is washed with deionized 5 times, 50 DEG C
It is dried in vacuo 2h, obtains the catalyst E.
Embodiment 6
It weighs 0.04g graphite oxide to be added in 20mL deionized water, be ultrasonically treated, supersonic frequency 180W, room temperature
After ultrasonic, the PdCl of the 0.02mol/L of 0.5mL is added into solution by ultrasonic 1.5h2The ascorbic acid of solution and 100mg,
The ultrasound 5min at 160W, 60 DEG C of reaction 1.5h of heating water bath, is centrifugated after reaction, is washed with deionized 5 times, and 50
DEG C vacuum drying 2h, obtains the catalyst F.
Embodiment 7
It weighs 0.04g graphite oxide to be added in 20mL deionized water, be ultrasonically treated, supersonic frequency 180W, room temperature
After ultrasonic, the PdCl of the 0.02mol/L of 0.5mL is added into solution by ultrasonic 1.5h2The ascorbic acid of solution and 80mg,
The ultrasound 5min at 240W, 90 DEG C of reaction 0.5h of heating water bath, is centrifugated after reaction, is washed with deionized 5 times, and 50
DEG C vacuum drying 2h, obtains the catalyst G.
Embodiment 8
It weighs 0.04g graphite oxide to be added in 20mL deionized water, be ultrasonically treated, supersonic frequency 180W, room temperature
After ultrasonic, the PdCl of the 0.02mol/L of 0.5mL is added into solution by ultrasonic 1.5h2The ascorbic acid of solution and 80mg,
The ultrasound 5min at 200W, 80 DEG C of reaction 2h of heating water bath, is centrifugated after reaction, is washed with deionized 5 times, 50 DEG C
It is dried in vacuo 2h, obtains the catalyst H.
Catalyst in above-described embodiment is applied in 1- hexene hydrogenation process, reaction condition is as follows:
Solvent: ethyl alcohol；1- hexene/Pd (mol/mol): 2.8 × 104；Hydrogen Vapor Pressure: 1.0MPa；Reaction temperature: 30 DEG C；
Reaction time: 1h.
Its catalytic performance is as shown in table 1:
The catalytic performance of 1 catalyst of table
| Catalyst | 1- hexene conversion ratio (%) | N-hexane selectivity (%) | Catalyst recovery yield (%) |
| A | 78.3 | 100 | 92.6 |
| B | 99.5 | 100 | 96.7 |
| C | 100 | 100 | 97.5 |
| D | 87.9 | 100 | 97.7 |
| E | 95.3 | 100 | 97.1 |
| F | 78.6 | 100 | 96.4 |
| G | 88.1 | 100 | 97.6 |
| H | 93.7 | 100 | 95.8 |
As it can be seen from table 1 catalyst of the present invention is used for 1- hexene plus hydrogen, at 30 DEG C, highest conversion
For rate up to 100%, and in addition to catalyst A, the rate of recovery of other catalyst is above 95%.Very good solution is graphene-based
The recycling problem of catalyst.
Multiplexing performance investigation is carried out to the catalyst C that above-described embodiment 3 obtains, catalyst centrifugation is recycled and washed through ethyl alcohol
It is multiplexed after washing drying, performance is as shown in table 2:
The multiplexing performance of 2 catalyst C of table
| Multiplexing number | 1- hexene conversion ratio (%) | N-hexane selectivity (%) |
| 1 | 100 | 100 |
| 2 | 99.6 | 100 |
| 3 | 100 | 100 |
| 4 | 99.7 | 100 |
| 5 | 99.5 | 100 |
| 6 | 99.8 | 100 |
For the display catalyst of table 2 using activity after 6 times almost without decline, multiplexing performance is good.
Taking the above-mentioned ideal embodiment according to the present invention as inspiration, through the above description, relevant staff is complete
Various changes and amendments can be carried out without departing from the scope of the technological thought of the present invention' entirely.The technology of this invention
Property range is not limited to the contents of the specification, it is necessary to which the technical scope thereof is determined according to the scope of the claim.
Claims (2)
1. a kind of three-dimensional redox graphene load nano Pd particle hydrogenation catalyst is prepared in n-hexane in catalysis reduction 1- hexene
Application, it is characterised in that the catalyst be using three-dimensional redox graphene as carrier, using nano Pd particle as active component, use
One step hydro thermal method is made, and this method specifically carries out as steps described below:
(1) it weighs a certain amount of graphite oxide to be added into deionized water, graphite oxide concentration is 0.5-4mg/mL, then in room temperature
Lower ultrasound, the graphene oxide solution dispersed；
(2) the 0.02mol/L PdCl of 0.3-1mL is added into step (1) resulting solution2Aqueous solution and 60-100mg's is anti-
Bad hematic acid, handles the solution under certain ultrasound condition, after ultrasound by solution at 60-90 DEG C hydro-thermal process 0.5-
Acquired solution is centrifugated by 2h, is washed with deionized, and is dried in vacuo to get the catalyst is arrived.
2. applying according to claim 1, it is characterised in that ultrasound condition described in step (2) is: supersonic frequency 120-
240W, time 5-20min.
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| CN107597103B (en) * | 2017-09-05 | 2019-12-27 | 大连理工大学 | Preparation method and application of three-dimensional structure graphene assembly catalyst for liquid phase hydrogenation |
| CN107970930A (en) * | 2017-11-23 | 2018-05-01 | 北京林业大学 | A kind of bimetal nano particles and single-layer graphene construct three-dimensional porous grapheme material and its preparation method and application jointly |
| CN108067221B (en) * | 2017-12-22 | 2020-05-22 | 四川理工学院 | Preparation method of superfine modified fly ash-graphene oxide-palladium hydrogenation catalyst |
| CN108295843B (en) * | 2018-01-19 | 2020-05-26 | 常州大学 | Three-dimensional graphene loaded nano Pd catalyst prepared by soft template method and application of catalyst in nitrobenzene hydrogenation |
| CN108144654B (en) * | 2018-01-30 | 2020-02-14 | 常州大学 | Three-dimensional graphene-loaded nano Pd catalyst prepared by phenolic crosslinking method and application of catalyst in nitrobenzene hydrogenation |
| CN114006001A (en) * | 2021-11-11 | 2022-02-01 | 四川烯都科技有限公司 | Preparation method of high-dispersity graphene nano palladium crystal particles |
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Application publication date: 20160928 Assignee: Senbiao Technology Services (Shandong) Co.,Ltd. Assignor: CHANGZHOU University Contract record no.: X2023980051006 Denomination of invention: Preparation method of three-dimensional reduced graphene oxide supported nano Pd hydrogenation catalyst Granted publication date: 20190125 License type: Common License Record date: 20231209 |