CN109847749A - The high performance catalyst and preparation method thereof of nitro-aromatic reduction at room temperature - Google Patents
The high performance catalyst and preparation method thereof of nitro-aromatic reduction at room temperature Download PDFInfo
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- CN109847749A CN109847749A CN201811630801.0A CN201811630801A CN109847749A CN 109847749 A CN109847749 A CN 109847749A CN 201811630801 A CN201811630801 A CN 201811630801A CN 109847749 A CN109847749 A CN 109847749A
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- 239000003054 catalyst Substances 0.000 title claims abstract description 44
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 239000004005 microsphere Substances 0.000 claims abstract description 17
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 14
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 4
- 239000002994 raw material Substances 0.000 claims abstract description 4
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 4
- 239000010703 silicon Substances 0.000 claims abstract description 4
- 238000007385 chemical modification Methods 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims description 18
- 239000012298 atmosphere Substances 0.000 claims description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- 238000000197 pyrolysis Methods 0.000 claims description 6
- 238000004458 analytical method Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 238000001237 Raman spectrum Methods 0.000 claims description 4
- 229910052786 argon Inorganic materials 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 4
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 238000001291 vacuum drying Methods 0.000 claims description 3
- 238000010792 warming Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 2
- 238000005245 sintering Methods 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 abstract description 4
- 238000002474 experimental method Methods 0.000 abstract description 2
- 229920000779 poly(divinylbenzene) Polymers 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 3
- 238000009841 combustion method Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003828 vacuum filtration Methods 0.000 description 3
- -1 Alkenyl benzene Chemical compound 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 208000005623 Carcinogenesis Diseases 0.000 description 2
- 238000003917 TEM image Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000036952 cancer formation Effects 0.000 description 2
- 231100000504 carcinogenesis Toxicity 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 230000005291 magnetic effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 150000005181 nitrobenzenes Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 229910018540 Si C Inorganic materials 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 230000005294 ferromagnetic effect Effects 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 238000002173 high-resolution transmission electron microscopy Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 208000005135 methemoglobinemia Diseases 0.000 description 1
- 239000002159 nanocrystal Substances 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
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- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses the high performance catalysts and preparation method thereof of nitro-aromatic reduction at room temperature, catalyst is using polydivinylbenezene microballoon as raw material, in such a way that silicon hydrogenation is to its surface chemical modification, obtain presoma microballoon, then it is pyrolyzed, final obtained surface is rich in the Si-C-Fe hybrid microspheres of Zero-valent Iron.Operation of the present invention is simple, and step is few, and experiment condition requirement is low, and gained hybrid microspheres regular shape, surface is smooth, and prepared hybrid microspheres have excellent catalytic properties.
Description
Technical field
The present invention relates to catalysis material fields, more particularly, to a kind of nitro-aromatic reduction high performance catalyst at room temperature
And preparation method thereof.
Background technique
Nitro-aromatic has been widely used in chemical industry, such as is used as explosive, insecticide, solvent, in addition, in bullet
The production of medicine, nitro-aromatic can also be generated by storing and discarding.Nitro-aromatic is that have carcinogenesis, genetoxic and interior to the mankind
The chemical substance for secreting chaff interferent, can also cause the diseases such as methemoglobinemia.Wherein, p-nitrophenol (4-NP) due to
Strong carcinogenesis, it is artificial caused by destructive and toxicity and primary pollutant is chosen as by Environmental Protection Agency USA, and its reduction
Product 4-aminophenol (4-AP) is widely used in synthesis analgesic drug product such as acamol, photographic developer, corrosion suppression
The chemical intermediate of preparation and dyestuff.Most of catalyst about 4-NP reduction research at present concentrates on noble metal nano grain
Son is such as Au, Pd, and on Pt and Ag, therefore it is still challenging to develop cheap and efficient catalyst.
It is an object of that present invention to provide a kind of new method for preparing nitro-aromatic catalyst for reduction under novel Room Temperature, this hairs
Bright to have the microballoon of metal small organic molecule as presoma using surface modification, being suitably pyrolyzed preparation, nitro-aromatic restores at room temperature
With catalyst, there is excellent catalytic activity in a series of reduction of nitrobenzene compounds and easily recycle and can be recycled
Performance.
Summary of the invention
In order to solve the problems in the existing technology, the present invention is by providing a kind of reduction of nitro-aromatic at room temperature use
High performance catalyst and preparation method thereof.
Specifically, the first purpose of the invention is to provide the high performance catalyst of nitro-aromatic reduction at room temperature, institute
Catalyst is stated with polydivinylbenezene microballoon (PDVB microballoon) for raw material, by silicon hydrogenation to PDVB microsphere surface
Modified mode is learned, presoma microballoon is obtained, then 500 DEG C~650 DEG C are pyrolyzed, and final obtained surface is rich in Zero-valent Iron
Si-C-Fe hybrid microspheres.
Wherein, prepared catalyst main component is carbon, and content is divided in 60%-80% range, and in Raman spectrum
I in analysisD/IG≤1.3。
A second object of the present invention is to provide the preparations of the high performance catalyst of the above-mentioned reduction of nitro-aromatic at room temperature
Method specifically comprises the following steps:
S1: presoma microballoon is prepared
Polydivinylbenezene microballoon, siliceous hydrogen ferrocene-containing compound and catalyst are added to toluene under an inert atmosphere
In, 60~100 DEG C of heating are reacted 8~16 hours after ultrasonic disperse, are then removed toluene using vacuum plant, are then washed
And vacuum drying;
The mass ratio that feeds intake of the polydivinylbenezene microballoon, siliceous hydrogen ferrocene-containing compound and catalyst is 1:4~5:
0.01, the dosage of toluene is 20 times of siliceous hydrogen ferrocene-containing compound volume;
S2: the pyrolysis in situ of presoma microballoon
Presoma microballoon after drying is placed in tube furnace, under an inert atmosphere, is warming up to 500 DEG C~650 DEG C sintering 3
~8h is subsequently cooled to environment temperature to get Si-C-Fe hybrid microspheres.
Preferably, the inert atmosphere is argon gas or nitrogen atmosphere.
Preferably, the residual double bonds of the polydivinylbenezene microballoon are measured through HBr addition process, and content is more than or equal to
2mmol/g。
Preferably, the siliceous hydrogen ferrocene-containing compound is 1,1 '-bis- (dimetylsilyl) ferrocene.
Preferably, in S1, the catalyst is hydrosilylation catalyst.
Preferably, the hydrosilylation catalyst is platinum catalyst.
Preferably, in S1, vacuum drying temperature is 40~60 DEG C, drying time 12-24h.
Preferably, in S1, washing is specifically referred to successively using tetrahydrofuran, and acetone and ether wash 3 times respectively.
Preferably, in S2, the presoma microballoon after drying is placed in tube furnace, under an inert atmosphere, is warming up to 600 DEG C
It is sintered 6h.
Preferably, prepared catalyst main component is carbon, and content is in 60%-80% range, and in Raman spectrum
I in analysisD/IG≤1.3。
Compared with prior art, the beneficial effects of the present invention are:
1) easy to operate, step is few, and experiment condition requires low;2) gained hybrid microspheres regular shape, surface are smooth;3) institute
The hybrid microspheres of preparation have excellent catalytic properties.
The present invention has the microballoon of metal small organic molecule as presoma using surface modification, is suitably pyrolyzed preparation at room temperature
Nitro-aromatic catalyst for reduction.Pass through the residual ethylene base and 1,1 '-on PDVB microballoon (i.e. polydivinylbenezene microballoon) surface
Silicon hydrogenation between bis- (dimetylsilyl) ferrocene realizes the ferrocene chemical modification to PDVB microsphere surface, so
By pyrolysis under felicity condition to get the Si-C hydridization magnetic microsphere for arriving the novel nanocrystal containing Fe.Since it has typically
Micro- meso-hole structure, large specific surface area, richness sp2Hydridization carbon and the good feature of ferromagnetic property, therefore in a series of nitrobenzene chemical combination
Performance is recycled and can be recycled in the reduction of object with excellent catalytic activity and easily.The present invention is that synthesis has catalysis
Low cost magnetic hybrid microspheres material provide convenience, can be widely applied to sustainable conversion and the chemistry of environmental contaminants
Intermediate production.
Detailed description of the invention
In order to more clearly explain the embodiment of the invention or the technical proposal in the existing technology, to embodiment or will show below
There is attached drawing needed in technical description to be briefly described, it should be apparent that, the accompanying drawings in the following description is the present invention
Some embodiments for those of ordinary skill in the art without creative efforts, can also basis
These attached drawings obtain other attached drawings.
Fig. 1 is the TEM figure for the Si-C-Fe hybrid microspheres that the embodiment of the present invention 1 synthesizes, wherein (a) is low power TEM figure, (b)
It is high-resolution TEM figure, is (c) partial enlarged view of (b);
The enlarged drawing of (c) in Fig. 2 Fig. 1.
Specific embodiment
In order to enable those skilled in the art to more fully understand, technical solution of the present invention is practiced, below with reference to specific
The invention will be further described for embodiment, but illustrated embodiment is not as a limitation of the invention.
Unless otherwise defined, the hereinafter used all technical terms for being and the normally understood meaning of those skilled in the art
It is identical.Technical term used herein is intended merely to the purpose of description specific embodiment, is not intended to the limitation present invention
Protection scope.Unless otherwise specified, it the various raw materials used in the following embodiment of the present invention, reagent, instrument and sets
It is standby to be commercially available by market or be prepared by existing method.
Embodiment 1
Under argon gas (purity >=99.999%) atmosphere, 1gPDVB microballoon (i.e. poly- divinyl is sequentially added into dry combustion method bottle
Base benzene microballoon), the 1 of 4g, 1 '-bis- (dimetylsilyl) ferrocene, the Karstedt catalyst and 125mL of 0.01g be anhydrous
Toluene, after abundant ultrasonic disperse, by mixture in 80 DEG C of stirring 12h, isolated by vacuum filtration crude product successively uses tetrahydrofuran,
Acetone and ether wash 3 times, are dried in vacuo at 40 DEG C for 24 hours, after to obtain yellow sample be that target product ferrocene is modified
PDVB (is denoted as Fc-PDVB).Then, dried Fc-PDVB is heated to 600 DEG C of tubular types under argon gas (70mL/min) atmosphere
Pyrolysis 6h is carried out in furnace, is subsequently cooled to environment temperature (5 DEG C/min) and is obtained Si-C-Fe hybrid microspheres.Through Raman spectrum point
Analysis, ID/IG=1.25;Transmission electron microscope (TEM) analysis result is as shown in Figure 1, the TEM image of low power shows prepared sample tool
The spherical characteristic having had observes the rich region Fe (diameter 10nm) of nanoscale in powerful TEM image, in crystalline substance
Lattice striated, spacing of lattice are 2.03 angstroms.
Embodiment 2
Under nitrogen (purity >=99.999%) atmosphere, PDVB microballoon (the i.e. poly- diethyl of 2g is sequentially added into dry combustion method bottle
Alkenyl benzene microballoon), the 1 of 8.5g, 1 '-bis- (dimetylsilyl) ferrocene, the Karstedt catalyst and 200mL of 0.02g
Dry toluene, after abundant ultrasonic disperse, by mixture in 60 DEG C of stirring 8h, isolated by vacuum filtration crude product successively uses tetrahydro furan
Mutter, acetone and ether wash 3 times, be dried in vacuo 12h at 60 DEG C, after to obtain yellow sample be that target product ferrocene is modified
PDVB (is denoted as Fc-PDVB).Then, dried Fc-PDVB is heated to 500 DEG C of tubular types under nitrogen (70mL/min) atmosphere
Pyrolysis 8h is carried out in furnace, is subsequently cooled to environment temperature (5 DEG C/min) and is obtained Si-C-Fe hybrid microspheres.
Embodiment 3
Under nitrogen (purity >=99.999%) atmosphere, PDVB microballoon (the i.e. poly- diethyl of 1g is sequentially added into dry combustion method bottle
Alkenyl benzene microballoon), the 1 of 5g, 1 '-bis- (dimetylsilyl) ferrocene, the Karstedt catalyst and 156mL of 0.01g without
Water-toluene, after abundant ultrasonic disperse, by mixture in 80 DEG C of stirring 12h, isolated by vacuum filtration crude product successively uses tetrahydro furan
Mutter, acetone and ether wash 3 times, be dried in vacuo at 40 DEG C for 24 hours, after to obtain yellow sample be that target product ferrocene is modified
PDVB (is denoted as Fc-PDVB).Then, dried Fc-PDVB is heated to 650 DEG C of tubular types under nitrogen (70mL/min) atmosphere
Pyrolysis 3h is carried out in furnace, is subsequently cooled to environment temperature (5 DEG C/min) and is obtained Si-C-Fe hybrid microspheres.
Obviously, various changes and modifications can be made to the invention without departing from essence of the invention by those skilled in the art
Mind and range.In this way, if these modifications and changes of the present invention belongs to the range of the claims in the present invention and its equivalent technologies
Within, then the present invention is also intended to include these modifications and variations.Embodiment described above is only to absolutely prove the present invention
And the preferred embodiment lifted, protection scope are without being limited thereto.Those skilled in the art institute on the basis of the present invention
The equivalent substitute or transformation of work, within the scope of the present invention, protection scope of the present invention is subject to claims.
Claims (10)
1. the high performance catalyst of nitro-aromatic reduction at room temperature, which is characterized in that the catalyst is with polydivinylbenezene
Microballoon is raw material, in such a way that silicon hydrogenation carries out chemical modification to its surface, obtains presoma microballoon, then 500 DEG C
~650 DEG C are pyrolyzed, and final obtained surface is rich in the Si-C-Fe hybrid microspheres of Zero-valent Iron.
2. the high performance catalyst of the reduction of nitro-aromatic at room temperature according to claim 1, which is characterized in that prepared
Catalyst main component be carbon, content is in 60%-80% range, and the I in Raman spectrum analysisD/IG≤1.3。
3. the preparation method of the high performance catalyst of the reduction of nitro-aromatic at room temperature according to claim 1, feature
It is, specifically comprises the following steps:
S1: presoma microballoon is prepared
Polydivinylbenezene microballoon, siliceous hydrogen ferrocene-containing compound and catalyst are added in toluene under an inert atmosphere, surpassed
60~100 DEG C of heating are reacted 8~16 hours after sound dispersion, then remove toluene using vacuum plant, then carry out washing and very
Sky is dry;
The mass ratio that feeds intake of the polydivinylbenezene microballoon, siliceous hydrogen ferrocene-containing compound and catalyst is 1:4~5:0.01,
The dosage of toluene is 20 times of siliceous hydrogen ferrocene-containing compound volume;
S2: the pyrolysis in situ of presoma microballoon
Presoma microballoon after drying is placed in tube furnace, under an inert atmosphere, be warming up to 500 DEG C~650 DEG C sintering 3~
8h is subsequently cooled to environment temperature to get Si-C-Fe hybrid microspheres.
4. the preparation method of the high performance catalyst of the reduction of nitro-aromatic at room temperature according to claim 3, feature
It is, the inert atmosphere is argon gas or nitrogen atmosphere.
5. the preparation method of the high performance catalyst of the reduction of nitro-aromatic at room temperature according to claim 3, feature exist
In the residual double bonds of the polydivinylbenezene microballoon are measured through HBr addition process, and content is more than or equal to 2mmol/g.
6. the preparation method of the high performance catalyst of the reduction of nitro-aromatic at room temperature according to claim 3, feature
It is, the siliceous hydrogen ferrocene-containing compound is 1,1 '-bis- (dimetylsilyl) ferrocene.
7. the preparation method of the high performance catalyst of the reduction of nitro-aromatic at room temperature according to claim 3, feature
It is, in S1, the catalyst is hydrosilylation catalyst.
8. the preparation method of the high performance catalyst of the reduction of nitro-aromatic at room temperature according to claim 7, feature
It is, the hydrosilylation catalyst is Karstedt catalyst or platinum catalyst.
9. the preparation method of the high performance catalyst of the reduction of nitro-aromatic at room temperature according to claim 3, feature
It is, in S1, vacuum drying temperature is 40~60 DEG C, drying time 12-24h.
10. the preparation method of the high performance catalyst of the reduction of nitro-aromatic at room temperature according to claim 3, feature
It is, in S1, washing is specifically referred to successively using tetrahydrofuran, and acetone and ether wash 3 times respectively.
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103342357A (en) * | 2013-07-16 | 2013-10-09 | 安徽理工大学 | Low temperature catalytic graphitization method for polydivinylbenzene resin |
CN103979965A (en) * | 2014-05-12 | 2014-08-13 | 西北工业大学 | Method for preparing Si-C-N-based ceramic microspheres |
CN104190359A (en) * | 2014-09-03 | 2014-12-10 | 西北工业大学 | Porous grading Si-C-N hybrid material and preparation method thereof |
CN106311340A (en) * | 2016-09-28 | 2017-01-11 | 济南大学 | Preparation method of micron motor catalyst based on polydivinylbenzene (PDVB) porous beads |
-
2018
- 2018-12-29 CN CN201811630801.0A patent/CN109847749A/en active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103342357A (en) * | 2013-07-16 | 2013-10-09 | 安徽理工大学 | Low temperature catalytic graphitization method for polydivinylbenzene resin |
CN103979965A (en) * | 2014-05-12 | 2014-08-13 | 西北工业大学 | Method for preparing Si-C-N-based ceramic microspheres |
CN104190359A (en) * | 2014-09-03 | 2014-12-10 | 西北工业大学 | Porous grading Si-C-N hybrid material and preparation method thereof |
CN106311340A (en) * | 2016-09-28 | 2017-01-11 | 济南大学 | Preparation method of micron motor catalyst based on polydivinylbenzene (PDVB) porous beads |
Non-Patent Citations (2)
Title |
---|
XIAOFEI ZHANG ET.AL: ""Constructing magnetic Si–C–Fe hybrid microspheres for room temperature nitroarenes reduction"", 《JOURNAL OF MATERIALS CHEMISTRY A》 * |
XIAOFEI ZHANG ET.AL: "Novel ferrocene-containing organosilicon polymers and uniform microspheres prepared by free radical copolymerization: Precursors for magnetic Si-C-Fe-(O) nanomaterials", 《MATERIALS AND DESIGN》 * |
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