CN108097315A - A kind of support type NH2The synthetic method of-UiO-66 hydrogenation catalysts and application - Google Patents
A kind of support type NH2The synthetic method of-UiO-66 hydrogenation catalysts and application Download PDFInfo
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- CN108097315A CN108097315A CN201711146266.7A CN201711146266A CN108097315A CN 108097315 A CN108097315 A CN 108097315A CN 201711146266 A CN201711146266 A CN 201711146266A CN 108097315 A CN108097315 A CN 108097315A
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- hydrogenation catalysts
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- 239000003054 catalyst Substances 0.000 title claims abstract description 46
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 44
- 238000010189 synthetic method Methods 0.000 title claims abstract description 17
- 239000013207 UiO-66 Substances 0.000 title claims description 46
- 239000010970 precious metal Substances 0.000 claims abstract description 11
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000001027 hydrothermal synthesis Methods 0.000 claims abstract description 6
- 239000012266 salt solution Substances 0.000 claims abstract description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 239000013110 organic ligand Substances 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 10
- 229910052726 zirconium Inorganic materials 0.000 claims description 10
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- OERNJTNJEZOPIA-UHFFFAOYSA-N zirconium nitrate Chemical compound [Zr+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O OERNJTNJEZOPIA-UHFFFAOYSA-N 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- GPNNOCMCNFXRAO-UHFFFAOYSA-N 2-aminoterephthalic acid Chemical compound NC1=CC(C(O)=O)=CC=C1C(O)=O GPNNOCMCNFXRAO-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 239000013049 sediment Substances 0.000 claims description 4
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical group Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 claims description 4
- WGLQHUKCXBXUDV-UHFFFAOYSA-N 3-aminophthalic acid Chemical class NC1=CC=CC(C(O)=O)=C1C(O)=O WGLQHUKCXBXUDV-UHFFFAOYSA-N 0.000 claims description 3
- NGIISMJJMXRCCT-UHFFFAOYSA-N [Ru].[N+](=O)(O)[O-] Chemical group [Ru].[N+](=O)(O)[O-] NGIISMJJMXRCCT-UHFFFAOYSA-N 0.000 claims description 3
- 229960000583 acetic acid Drugs 0.000 claims description 3
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 claims description 3
- RWRDJVNMSZYMDV-UHFFFAOYSA-L radium chloride Chemical compound [Cl-].[Cl-].[Ra+2] RWRDJVNMSZYMDV-UHFFFAOYSA-L 0.000 claims description 3
- 229910001630 radium chloride Inorganic materials 0.000 claims description 3
- 239000012362 glacial acetic acid Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 claims description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 abstract description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract description 4
- 230000003197 catalytic effect Effects 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- 229910052751 metal Inorganic materials 0.000 abstract description 3
- 239000002184 metal Substances 0.000 abstract description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 abstract description 2
- 239000006185 dispersion Substances 0.000 abstract description 2
- 229910052763 palladium Inorganic materials 0.000 abstract description 2
- 229910052697 platinum Inorganic materials 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 229910052703 rhodium Inorganic materials 0.000 abstract description 2
- 239000010948 rhodium Substances 0.000 abstract description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052707 ruthenium Inorganic materials 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 3
- 239000012621 metal-organic framework Substances 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- 238000006000 Knoevenagel condensation reaction Methods 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000002153 concerted effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 150000007517 lewis acids Chemical group 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/1691—Coordination polymers, e.g. metal-organic frameworks [MOF]
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
- B01J35/391—Physical properties of the active metal ingredient
- B01J35/394—Metal dispersion value, e.g. percentage or fraction
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
- B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
- B01J2231/643—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of R2C=O or R2C=NR (R= C, H)
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
- B01J2531/48—Zirconium
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
A kind of support type NH2The synthetic method of 66 hydrogenation catalysts of UiO and application, belong to catalyst synthesis technology field.NH is synthesized by hydro-thermal method first2Then UiO 66 impregnates precious metal salt solution (such as ruthenium, rhodium, palladium, platinum), finally obtains support type NH266 hydrogenation catalysts of UiO, the catalyst can be applied to the hydrogenation catalyst reaction of vanillic aldehyde.Support type NH produced by the present invention2The characteristics of 66 hydrogenation catalysts of UiO have large specific surface area, and metal dispersion is good, and hydrogenation activity site is more, and the hydrogenation catalyst preparation method is simple, and catalytic activity is strong, and catalyst stability is good, is expected to realize commercial Application.
Description
(1) technical field
The present invention relates to a kind of support type NH2The synthetic method of-UiO-66 hydrogenation catalysts and application belong to catalyst conjunction
Into technical field.
(2) background technology
UiO-66 is a kind of metal-organic framework materials (MOFs) with good thermal stability and chemical stability,
NH2- UiO-66 is the amination material of UiO-66, it is with Zr4+For metal, prepared by ligand of 2- amino terephthalic acid (TPA)
's.NH2There is Lewis acid (Zr in-UiO-66 materials4+) and weak base (- NH2) concerted catalysis effect, have been found
Excellent catalytic performance is shown in Knoevenagel condensation reactions and in Cross-condensation reaction.
The present invention has synthesized a kind of support type NH2- UiO-66 hydrogenation catalysts, with NH2- UiO-66 is carrier, passes through load
Noble metal (such as ruthenium, rhodium, palladium, platinum etc.), obtains obtaining support type NH2- UiO-66 hydrogenation catalysts, can be applied to vanillic aldehyde
Hydrogenation catalyst reacts.
(3) content of the invention
A kind of support type NH of the present invention2The synthetic method of-UiO-66 hydrogenation catalysts and application specifically include following step
Suddenly：
(1) the zirconium source of 30~70mg, the organic ligand of 100~150mg, 0.5~4ml acid solutions and 1~10ml are weighed
Dimethylformamide, after mixing, be 1~5h of hydro-thermal process at 100~150 DEG C in temperature, obtain mixture.
Zirconium source described in step (1) is zirconium chloride, one kind in zirconium nitrate；Organic ligand is 2- amino terephthaldehydes
One kind in acid, 3- aminophthalic acids；Acid solution is hydrochloric acid, one kind in glacial acetic acid.
(2) mixture in step (1) is stood into 12~48h at room temperature, then carries out centrifugal treating, precipitated
Object, then washed respectively 2~4 times using dimethylformamide and absolute ethyl alcohol successively, vacuum at being finally 50~80 DEG C in temperature
Dry 12~48h is to get to NH2-UiO-66。
(3) NH for obtaining step (2)2- UiO-66 is put into the precious metal salt solution that mass concentration is 1~2%, stirring
Then 10~48h is washed with acetone, be dried in vacuo 12~48h in the case where temperature is 50~80 DEG C, finally obtain support type NH2-
UiO-66 hydrogenation catalysts.
Precious metal salt described in step (3) is nitric acid ruthenium, one kind in radium chloride, palladium nitrate, platinum chloride.
A kind of support type NH of the present invention2- UiO-66 hydrogenation catalysts can be applied to the hydrogenation catalyst reaction of vanillic aldehyde.
The advantage of the invention is that：
1st, a kind of support type NH proposed by the present invention2The synthetic method of-UiO-66 hydrogenation catalysts and application, with NH2-
The characteristics of UiO-66 is carrier, has large specific surface area, and metal dispersion is good, and hydrogenation activity site is more.
2nd, a kind of support type NH proposed by the present invention2The synthetic method of-UiO-66 hydrogenation catalysts and application, the hydrogenation are urged
Agent preparation method is simple, and catalytic activity is strong, and catalyst stability is good, is expected to realize commercial Application.
(4) illustrate
Fig. 1：A kind of support type NH proposed by the present invention2The synthetic method of-UiO-66 hydrogenation catalysts and the technique of application
Flow chart.
(5) specific embodiment
The technical characterstic of the present invention is described in detail below in conjunction with the drawings and specific embodiments, as shown in Figure 1.
Embodiment 1：
A kind of support type NH of the present invention2The synthetic method of-UiO-66 hydrogenation catalysts and application specifically include following step
Suddenly：
(1) dimethylformamide of the zirconium source of 50mg, the organic ligand of 120mg, 1.5ml acid solutions and 5ml are weighed, is mixed
After closing uniformly, the hydro-thermal process 3h in the case where temperature is 120 DEG C obtains mixture.
Zirconium source described in step (1) is zirconium chloride；Organic ligand is 2- amino terephthalic acid (TPA)s；Acid solution is salt
Acid.
(2) mixture in step (1) is stood for 24 hours at room temperature, then carries out centrifugal treating, obtain sediment, then
Washed respectively 3 times using dimethylformamide and absolute ethyl alcohol successively, be finally dried in vacuo in the case where temperature is 60 DEG C for 24 hours to get
To NH2-UiO-66。
(3) NH for obtaining step (2)2- UiO-66 is put into the precious metal salt solution that mass concentration is 1.5%, stirring
For 24 hours, then washed with acetone, be dried in vacuo for 24 hours in the case where temperature is 60 DEG C, finally obtain support type NH2- UiO-66 hydrogenation catalysts
Agent.
Precious metal salt described in step (3) is nitric acid ruthenium.
A kind of support type NH of the present invention2- UiO-66 hydrogenation catalysts can be applied to the hydrogenation catalyst reaction of vanillic aldehyde.
The result shows that support type NH2- UiO-66 hydrogenation catalysts are in the 30min of reaction to the conversion ratio energy of vanillic aldehyde
Reach 98%, selectivity of product reaches 95%.
Embodiment 2：
A kind of support type NH of the present invention2The synthetic method of-UiO-66 hydrogenation catalysts and application specifically include following step
Suddenly：
(1) dimethylformamide of the zirconium source of 30mg, the organic ligand of 100mg, 0.5ml acid solutions and 1ml are weighed, is mixed
After closing uniformly, the hydro-thermal process 5h in the case where temperature is 100 DEG C obtains mixture.
Zirconium source described in step (1) is zirconium nitrate；Organic ligand is 3- aminophthalic acids；Acid solution is salt
Acid.
(2) mixture in step (1) is stood into 12h at room temperature, then carries out centrifugal treating, obtain sediment, then
Washed respectively 2 times using dimethylformamide and absolute ethyl alcohol successively, be finally dried in vacuo in the case where temperature is 50 DEG C 48h to get
To NH2-UiO-66。
(3) NH for obtaining step (2)2- UiO-66 is put into the precious metal salt solution that mass concentration is 1%, stirring
Then 10h is washed with acetone, be dried in vacuo 48h in the case where temperature is 50 DEG C, finally obtain support type NH2- UiO-66 hydrogenation catalysts
Agent.
Precious metal salt described in step (3) is radium chloride.
A kind of support type NH of the present invention2- UiO-66 hydrogenation catalysts can be applied to the hydrogenation catalyst reaction of vanillic aldehyde.
The result shows that support type NH2- UiO-66 hydrogenation catalysts are in the 30min of reaction to the conversion ratio energy of vanillic aldehyde
Reach 95%, selectivity of product reaches 90%.
Embodiment 3：
A kind of support type NH of the present invention2The synthetic method of-UiO-66 hydrogenation catalysts and application specifically include following step
Suddenly：
(1) dimethylformamide of the zirconium source of 70mg, the organic ligand of 150mg, 4ml acid solutions and 10ml are weighed, is mixed
After closing uniformly, the hydro-thermal process 1h in the case where temperature is 150 DEG C obtains mixture.
Zirconium source described in step (1) is zirconium chloride；Organic ligand is 2- amino terephthalic acid (TPA)s；Acid solution is ice vinegar
Acid.
(2) mixture in step (1) is stood into 12h at room temperature, then carries out centrifugal treating, obtain sediment, then
Washed respectively 4 times using dimethylformamide and absolute ethyl alcohol successively, be finally dried in vacuo in the case where temperature is 80 DEG C 12h to get
To NH2-UiO-66。
(3) NH for obtaining step (2)2- UiO-66 is put into the precious metal salt solution that mass concentration is 2%, stirring
Then 48h is washed with acetone, be dried in vacuo 12h in the case where temperature is 80 DEG C, finally obtain support type NH2- UiO-66 hydrogenation catalysts
Agent.
Precious metal salt described in step (3) is palladium nitrate.
A kind of support type NH of the present invention2- UiO-66 hydrogenation catalysts can be applied to the hydrogenation catalyst reaction of vanillic aldehyde.
The result shows that support type NH2- UiO-66 hydrogenation catalysts are in the 30min of reaction to the conversion ratio energy of vanillic aldehyde
Reach 90%, selectivity of product reaches 92%.
Claims (6)
1. a kind of support type NH2The synthetic method of-UiO-66 hydrogenation catalysts and application, which is characterized in that this method specifically includes
Following steps：
(1) the two of the zirconium source of 30~70mg, the organic ligand of 100~150mg, 0.5~4ml acid solutions and 1~10ml are weighed
Methylformamide, after mixing, 1~5h of hydro-thermal process in the case where temperature is 100~150 DEG C obtains mixture；
(2) mixture in step (1) is stood into 12~48h at room temperature, then carries out centrifugal treating, obtain sediment, then
It is washed respectively 2~4 times using dimethylformamide and absolute ethyl alcohol successively, is finally dried in vacuo 12 in the case where temperature is 50~80 DEG C
~48h is to get to NH2-UiO-66；
(3) NH for obtaining step (2)2- UiO-66 is put into the precious metal salt solution that mass concentration is 1~2%, and stirring 10~
Then 48h is washed with acetone, be dried in vacuo 12~48h in the case where temperature is 50~80 DEG C, finally obtain support type NH2-UiO-66
Hydrogenation catalyst.
2. a kind of support type NH according to claim 12The synthetic method of-UiO-66 hydrogenation catalysts and application, feature
It is：The zirconium source is zirconium chloride, one kind in zirconium nitrate.
3. a kind of support type NH according to claim 12The synthetic method of-UiO-66 hydrogenation catalysts and application, feature
It is：The organic ligand is 2- amino terephthalic acid (TPA), one kind in 3- aminophthalic acids.
4. a kind of support type NH according to claim 12The synthetic method of-UiO-66 hydrogenation catalysts and application, feature
It is：The acid solution is hydrochloric acid, one kind in glacial acetic acid.
5. a kind of support type NH according to claim 12The synthetic method of-UiO-66 hydrogenation catalysts and application, feature
It is：The precious metal salt is nitric acid ruthenium, one kind in radium chloride, palladium nitrate, platinum chloride.
6. a kind of support type NH according to claim 12The synthetic method of-UiO-66 hydrogenation catalysts and application, feature
It is：The hydrogenation catalyst that it is applied to vanillic aldehyde reacts.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201711146266.7A CN108097315A (en) | 2017-11-17 | 2017-11-17 | A kind of support type NH2The synthetic method of-UiO-66 hydrogenation catalysts and application |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201711146266.7A CN108097315A (en) | 2017-11-17 | 2017-11-17 | A kind of support type NH2The synthetic method of-UiO-66 hydrogenation catalysts and application |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110665546A (en) * | 2019-09-03 | 2020-01-10 | 北京氦舶科技有限责任公司 | Noble metal/amino MOFs selective hydrogenation catalyst, preparation method and application thereof |
| CN111054443A (en) * | 2019-12-26 | 2020-04-24 | 华南理工大学 | Zirconium-based MOF catalyst loaded with double active sites and preparation method and application thereof |
| CN111359672A (en) * | 2020-03-31 | 2020-07-03 | 上海应用技术大学 | UiO-67 loaded Rh-based catalyst, and preparation method and application thereof |
| CN113083365A (en) * | 2021-04-06 | 2021-07-09 | 中山大学 | Preparation method and application of high-hydrogenation-selectivity Pt-based alloy/MOFs catalyst |
| CN114797991A (en) * | 2022-03-24 | 2022-07-29 | 北京化工大学 | Rubber hydrogenation catalyst, preparation method, recovery method and application thereof |
-
2017
- 2017-11-17 CN CN201711146266.7A patent/CN108097315A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110665546A (en) * | 2019-09-03 | 2020-01-10 | 北京氦舶科技有限责任公司 | Noble metal/amino MOFs selective hydrogenation catalyst, preparation method and application thereof |
| CN111054443A (en) * | 2019-12-26 | 2020-04-24 | 华南理工大学 | Zirconium-based MOF catalyst loaded with double active sites and preparation method and application thereof |
| CN111359672A (en) * | 2020-03-31 | 2020-07-03 | 上海应用技术大学 | UiO-67 loaded Rh-based catalyst, and preparation method and application thereof |
| CN111359672B (en) * | 2020-03-31 | 2023-02-07 | 上海应用技术大学 | UiO-67 loaded Rh-based catalyst, and preparation method and application thereof |
| CN113083365A (en) * | 2021-04-06 | 2021-07-09 | 中山大学 | Preparation method and application of high-hydrogenation-selectivity Pt-based alloy/MOFs catalyst |
| CN113083365B (en) * | 2021-04-06 | 2022-02-18 | 中山大学 | Preparation method and application of high-hydrogenation-selectivity Pt-based alloy/MOFs catalyst |
| CN114797991A (en) * | 2022-03-24 | 2022-07-29 | 北京化工大学 | Rubber hydrogenation catalyst, preparation method, recovery method and application thereof |
| CN114797991B (en) * | 2022-03-24 | 2023-09-01 | 北京化工大学 | Rubber hydrogenation catalyst, preparation method, recovery method and application thereof |
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Application publication date: 20180601 |