CN110194730A - Application of the DUT-67 (Zr) in photochemical catalytic oxidation aminomethyl phenyl thioether preparation methyl phenyl sulfoxide - Google Patents
Application of the DUT-67 (Zr) in photochemical catalytic oxidation aminomethyl phenyl thioether preparation methyl phenyl sulfoxide Download PDFInfo
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- CN110194730A CN110194730A CN201910597146.1A CN201910597146A CN110194730A CN 110194730 A CN110194730 A CN 110194730A CN 201910597146 A CN201910597146 A CN 201910597146A CN 110194730 A CN110194730 A CN 110194730A
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- aminomethyl phenyl
- catalytic oxidation
- photochemical catalytic
- organic framework
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- 239000013432 DUT-67 Substances 0.000 title claims abstract description 33
- YWOQNRUBCZGGTI-UHFFFAOYSA-N phenylsulfanylmethanamine Chemical compound NCSC1=CC=CC=C1 YWOQNRUBCZGGTI-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 230000003647 oxidation Effects 0.000 title claims abstract description 14
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 14
- 230000003197 catalytic effect Effects 0.000 title claims abstract description 12
- JXTGICXCHWMCPM-UHFFFAOYSA-N (methylsulfinyl)benzene Chemical compound CS(=O)C1=CC=CC=C1 JXTGICXCHWMCPM-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 239000012621 metal-organic framework Substances 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 239000000463 material Substances 0.000 claims abstract description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- 238000006555 catalytic reaction Methods 0.000 claims description 7
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000011259 mixed solution Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- 229910007932 ZrCl4 Inorganic materials 0.000 claims description 5
- 238000001027 hydrothermal synthesis Methods 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000012265 solid product Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 229910052724 xenon Inorganic materials 0.000 claims description 3
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 claims description 3
- 238000001514 detection method Methods 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 229910007926 ZrCl Inorganic materials 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 238000007146 photocatalysis Methods 0.000 abstract description 8
- 230000001699 photocatalysis Effects 0.000 abstract description 8
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 238000000034 method Methods 0.000 abstract description 4
- 238000005516 engineering process Methods 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 230000001988 toxicity Effects 0.000 abstract description 2
- 231100000419 toxicity Toxicity 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 230000001681 protective effect Effects 0.000 abstract 1
- 239000013096 zirconium-based metal-organic framework Substances 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- -1 sulfur ether compound Chemical class 0.000 description 3
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 3
- 229910007746 Zr—O Inorganic materials 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000013207 UiO-66 Substances 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 239000010953 base metal Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 239000013384 organic framework Substances 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YCGAZNXXGKTASZ-UHFFFAOYSA-N thiophene-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)S1 YCGAZNXXGKTASZ-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/2243—At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
-
- 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
- B01J35/39—Photocatalytic properties
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
-
- 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
- B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
The invention discloses application of the Zr-MOF (DUT-67) in photochemical catalytic oxidation aminomethyl phenyl thioether preparation methyl phenyl sulfoxide, belong to photocatalysis technology field.DUT-67 (Zr) is a kind of thermostabilization with higher and chemically stable metal-organic framework materials.DUT-67 (Zr) is carried out organic synthesis as photochemical catalyst for the first time by the present invention, has further expanded application of the Zr base MOF in photocatalysis field of high stability.Under the light source of all band and 360nm wavelength, DUT-67 (Zr) shows higher activity in photochemical catalytic oxidation aminomethyl phenyl thioether, and the reaction process that can successfully solve in traditional preparation process is complicated, and toxicity is high, easy to pollute, the problem of low efficiency.Present invention process is simple, environmentally protective, and yield is high, and catalytic process stability and high efficiency can be applied to large-scale actual production, has wide potentiality.
Description
Technical field
The invention belongs to photocatalysis technology fields, are specifically described a kind of Zr Base Metal-organic framework of high stable
DUT-67 (Zr) is applied to photocatalysis field.
Background technique
The three-dimensional porous network knot that metal-organic framework materials (MOFs) are assembled by metal ion and organic ligand
Structure has many advantages, such as that large specific surface area, stability height and controllable ability are strong.In recent years, MOFs has been widely used in light
It is catalyzed organic synthesis, CO2Reduction, the fields such as photodissociation aquatic products hydrogen and degradation of organic substances.Zr base MOF by biggish specific surface area and
Excellent structural stability is shown one's talent in numerous MOF.To currently, most of researchs concentrate on the modification of UiO-66, having must
New Zr base MOF is expanded in the application of photocatalysis field.Based on the above reasons, DUT-67 (Zr) is used as in Zr base MOF and has
A member of potentiality provides new thinking for the selection of photochemical catalyst.
Sulfoxide has obtained more and more people's as medicine, the organic intermediate of pesticide and expensive material, preparation method
Concern, selectively oxidizing sulfur ether compound is one of most common synthetic method.But traditional industrial preparative method has toxicity
The photocatalysis technology of the disadvantages of height, low efficiency, poor selectivity, high-efficiency cleaning come into being.In conjunction with the excellent of DUT-67 (Zr) itself
Point and light-catalysed effect, this will better solve the difficulty during oxidation aminomethyl phenyl thioether synthesis of methyl phenyl sulfoxide
Topic.
Summary of the invention
It is an object of the invention to expand application of the Zr base MOFs in photocatalysis field, provides DUT-67 (Zr) light and urge
Change oxidation aminomethyl phenyl thioether synthesis of methyl phenyl sulfoxide.The conversion ratio of reactant and the selectivity of product are all good, and catalyst is steady
Qualitative height, operating method is easy to be controllable, with good application prospect.
To achieve the above object, the present invention adopts the following technical scheme that:
A kind of metal-organic framework materials DUT-67 (Zr) with photochemical catalytic oxidation aminomethyl phenyl thioether, chemical formula Zr6O4
(OH)4(TDC)4(CH3COO)4。
The metal-organic framework materials DUT-67 (Zr) is prepared applied to photochemical catalytic oxidation aminomethyl phenyl thioether
In methyl phenyl sulfoxide, wherein the DUT-67 (Zr) is used as light-catalyzed reaction agent；Specific steps are as follows: weigh 10 mg metals-
Organic framework materials DUT-67 (Zr) catalyst in reactor, be added 11.7 μ L aminomethyl phenyl thioethers, 0.1 mL methanol and
1.5 mL benzotrifluorides, are passed through oxygen, under normal temperature conditions, open light source and carry out light-catalyzed reaction, product passes through gas-chromatography
It detects and analyzes；The light source is the xenon lamp of 300 W.
The method of the application are as follows: utilizing benzotrifluoride and methanol is reaction dissolvent, and oxygen is as oxidant, in room temperature item
8 h of light-catalyzed reaction under part；The volume ratio of the benzotrifluoride and methanol is 15:1.
Two kinds of reaction results: 1) when light source range is all band, the conversion ratio of aminomethyl phenyl thioether is 99%, aminomethyl phenyl
The selectivity of sulfoxide is 99%.2) when optical source wavelength is greater than 360 nm, the conversion ratio of aminomethyl phenyl thioether is 95%, and aminomethyl phenyl is sub-
The selectivity of sulfone is 99%.
Wherein, DUT-67 (Zr) is prepared by one pot of hydro-thermal method.Specific steps: by ZrCl4(1 mmol, 230 mg)
It is dissolved in the mixed solution of 12.5 mL DMF (n,N-Dimethylformamide) and 12.5 mL NMP (N-Methyl pyrrolidone),
Stir 10 min to ZrCl4It is completely dissolved, by H2TDC (2,5- thiophene dicarboxylic acid) (0.67 mmol, 110 mg) is added to mixed
It closes in solution and after stirring 5 min, 7 mL acetic acid is added as regulator, continue to stir 10 min.Finally by suspended mixed liquor
It is transferred in the hydrothermal reaction kettle of 50 mL, is placed in baking oven, in 120 DEG C of 48 h of reaction.Solid product is obtained after filtering, is used
100 DEG C of vacuum drying after DMF and methanol repeatedly wash.
The remarkable advantage of this experiment is:
1) DUT-67 (Zr) is applied to photocatalysis field for the first time and realizes that aminomethyl phenyl thioether efficient oxidation synthesizes first by the present invention
Base phenylsulfone.
2) experimentation of the present invention is simple and easy to do, has stronger generalization.
Detailed description of the invention
Fig. 1 is the X-ray diffractogram (XRD) of catalyst DUT-67 (Zr) of the invention.
Fig. 2 is the UV-vis DRS figure (DRS) of catalyst DUT-67 (Zr) of the invention.
Fig. 3 is the Zr-O cluster schematic diagram of catalyst DUT-67 (Zr) of the invention.
Fig. 4 is the different light sources comparison of the invention with DUT-67 (Zr) for catalyst photochemical catalytic oxidation aminomethyl phenyl thioether
Lab diagram；Wherein 1 light source range is all band；2 optical source wavelength is greater than 360 nm.
Specific embodiment
It is several embodiments of the present invention below to make content of the present invention easily facilitate understanding, but this hair
It is bright to be not limited only to this.
The preparation of embodiment 1 DUT-67 (Zr) photochemical catalyst
By ZrCl4(1 mmol, 230 mg) are dissolved in 25mL(DMF:NMP=1:1) mixed solution in, stir 10 min to ZrCl4
It is completely dissolved, by H2TDC(0.67 mmol, 110 mg) be added in mixed solution and stir 5 min after, be added 7 mL acetic acid
As regulator, continue to stir 10 min.Finally suspended mixed liquor is transferred in the hydrothermal reaction kettle of 50 mL, is placed in baking
In case, in 120 DEG C of 48 h of reaction.Solid product is obtained after filtering, with 100 DEG C of vacuum bakings after DMF and methanol 3-5 times washing
It is dry.
Fig. 1 is the X-ray diffraction spectrogram of photochemical catalyst DUT-67 (Zr) of the invention, by comparison it is found that the sample of synthesis
Product are pure phases.Fig. 2 illustrates the UV-vis DRS spectrogram of photochemical catalyst DUT-67 (Zr) of the invention, can from figure
Sunlight can be effectively absorbed to DUT-67 (Zr).Fig. 3 illustrates the Zr-O clustering architecture of catalyst DUT-67 (Zr) of the invention
Figure, as can be seen from the figure DUT-67 (Zr) is by a Zr6What regular octahedron and 82,5- thiophene dicarboxylic acid's ligands were connected
Reo topological structure.
Embodiment 2 DUT-67 (Zr) photochemical catalytic oxidation aminomethyl phenyl thioether prepares methyl phenyl sulfoxide
The Zr Base Metal organic frame DUT-67 (Zr) of preparation is aoxidized into aminomethyl phenyl thioether as photochemical catalyst, weighs 10 mg
Catalyst is added 11.7 μ L aminomethyl phenyl thioethers, 0.1 mL methanol and 1.5 mL benzotrifluorides, is passed through oxygen in reactor,
Under normal temperature conditions, it opens light source and carries out light-catalyzed reaction, product passes through gas chromatographic detection and analyzes, and tests the light source used
It is the xenon lamp of 300 W.
The conversion ratio of aminomethyl phenyl thioether and the selection implementations of methyl phenyl sulfoxide are as shown in figure 4, can from figure
Out, when there is catalyst, under the conditions of all band (1), aminomethyl phenyl thioether conversion ratio after 8 h of illumination reaches 99%, selectively reaches
To 99%；Guaranteeing that incident optical range (2) in 360 nm or more, aminomethyl phenyl thioether convert after 8 h of illumination using optical filter
Rate reaches 95%, selectively reaches 99%.
The above is the preferable experimental example of this experiment, all equivalent changes done according to scope of the present invention patent with
Modification, is all covered by the present invention.
Claims (5)
1. a kind of metal-organic framework materials DUT-67 (Zr) with photochemical catalytic oxidation aminomethyl phenyl thioether, it is characterised in that:
Chemical formula is Zr6O4(OH)4(TDC)4(CH3COO)4。
2. a kind of preparation method of the metal-organic framework materials DUT-67 (Zr) with photochemical catalytic oxidation aminomethyl phenyl thioether,
It is characterized in that, specifically includes the following steps: by the ZrCl of 1 mmol4It is dissolved in the DMF/NMP mixed solution of 25 mL, stirs
10 min to ZrCl4It is completely dissolved, by the H of 0.67 mmol2After TDC is added in mixed solution and stirs 5 min, 7mL is added
Acetic acid continues to stir 10 min as regulator；Finally suspended mixed liquor is transferred in the hydrothermal reaction kettle of 50 mL, juxtaposition
In baking oven, in 120 DEG C of 48 h of reaction；Solid product is obtained after filtering, 100 DEG C of vacuum after being washed 3-5 times with DMF and methanol
Drying；
In the DMF/NMP mixed solution, the volume ratio of DMF and NMP are 1:1.
3. a kind of metal-organic framework materials DUT-67 (Zr) as described in claim 1 is in photochemical catalytic oxidation aminomethyl phenyl sulphur
Ether prepares the application in methyl phenyl sulfoxide, which is characterized in that the DUT-67 (Zr) is used as light-catalyzed reaction agent.
4. according to application described in right 2, it is characterised in that: utilizing benzotrifluoride and methanol is reaction dissolvent, and oxygen is as oxygen
Agent, under normal temperature conditions light-catalyzed reaction 8h；The volume ratio of the benzotrifluoride and methanol is 15:1.
5. according to application described in right 2, it is characterised in that: specific steps are as follows: weigh 10 mg metal-organic framework materials
11.7 μ L aminomethyl phenyl thioethers, 0.1 mL methanol and 1.5 mL fluoroforms are added in reactor in DUT-67 (Zr) catalyst
Benzene is passed through oxygen, under normal temperature conditions, opens light source and carries out light-catalyzed reaction, product passes through gas chromatographic detection and analyzes；Institute
State the xenon lamp that light source is 300 W.
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|---|---|---|---|
| CN201910597146.1A CN110194730B (en) | 2019-07-04 | 2019-07-04 | Application of DUT-67(Zr) in preparation of methyl phenyl sulfoxide through photocatalytic oxidation of methyl phenyl sulfide |
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| CN201910597146.1A CN110194730B (en) | 2019-07-04 | 2019-07-04 | Application of DUT-67(Zr) in preparation of methyl phenyl sulfoxide through photocatalytic oxidation of methyl phenyl sulfide |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110882727A (en) * | 2019-12-12 | 2020-03-17 | 吉林师范大学 | Triple-interpenetration metal organic framework heterogeneous CO2Cycloaddition catalyst, preparation method and application thereof |
| CN113024834A (en) * | 2021-03-22 | 2021-06-25 | 华中科技大学 | DUT-67 and batch preparation method and application thereof |
| CN113318794A (en) * | 2021-05-12 | 2021-08-31 | 江苏大学 | Preparation method and application of plasmon composite photocatalyst Pd/DUT-67 |
| CN113546687A (en) * | 2021-07-21 | 2021-10-26 | 海南大学 | Preparation method and application of visible light catalyst of ultrathin titanium-based MOFs nanosheets |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110882727A (en) * | 2019-12-12 | 2020-03-17 | 吉林师范大学 | Triple-interpenetration metal organic framework heterogeneous CO2Cycloaddition catalyst, preparation method and application thereof |
| CN113024834A (en) * | 2021-03-22 | 2021-06-25 | 华中科技大学 | DUT-67 and batch preparation method and application thereof |
| CN113318794A (en) * | 2021-05-12 | 2021-08-31 | 江苏大学 | Preparation method and application of plasmon composite photocatalyst Pd/DUT-67 |
| CN113318794B (en) * | 2021-05-12 | 2022-07-22 | 江苏大学 | Preparation method and application of plasmon composite photocatalyst Pd/DUT-67 |
| CN113546687A (en) * | 2021-07-21 | 2021-10-26 | 海南大学 | Preparation method and application of visible light catalyst of ultrathin titanium-based MOFs nanosheets |
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