CN105749977A - Method for preparing gold-ruthenium supported periodic mesoporous silicon catalyst - Google Patents
Method for preparing gold-ruthenium supported periodic mesoporous silicon catalyst Download PDFInfo
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- CN105749977A CN105749977A CN201610143875.6A CN201610143875A CN105749977A CN 105749977 A CN105749977 A CN 105749977A CN 201610143875 A CN201610143875 A CN 201610143875A CN 105749977 A CN105749977 A CN 105749977A
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- catalyst
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- ruthenium
- mesoporous silicon
- bimetallic
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- 239000003054 catalyst Substances 0.000 title claims abstract description 29
- 230000000737 periodic effect Effects 0.000 title claims abstract description 12
- 229910052710 silicon Inorganic materials 0.000 title claims abstract description 11
- 239000010703 silicon Substances 0.000 title claims abstract description 11
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims abstract description 10
- CQKBIUZEUFGQMZ-UHFFFAOYSA-N [Ru].[Au] Chemical compound [Ru].[Au] CQKBIUZEUFGQMZ-UHFFFAOYSA-N 0.000 title claims abstract description 4
- 238000000034 method Methods 0.000 title abstract description 9
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- -1 ethylphenyl Chemical group 0.000 claims description 9
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 claims description 3
- 239000010931 gold Substances 0.000 claims description 3
- 229910052737 gold Inorganic materials 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 238000007334 copolymerization reaction Methods 0.000 claims description 2
- UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 claims description 2
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000001179 sorption measurement Methods 0.000 claims description 2
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- 239000002210 silicon-based material Substances 0.000 abstract description 11
- 230000007062 hydrolysis Effects 0.000 abstract description 6
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 6
- 238000010523 cascade reaction Methods 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 5
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 238000012546 transfer Methods 0.000 abstract description 2
- SXWJMFFSUOWBDC-UHFFFAOYSA-N acetaldehyde;benzene Chemical class CC=O.C1=CC=CC=C1 SXWJMFFSUOWBDC-UHFFFAOYSA-N 0.000 abstract 1
- NEBFBVFMEJNMTO-UHFFFAOYSA-N acetylene;benzene Chemical group C#C.C1=CC=CC=C1 NEBFBVFMEJNMTO-UHFFFAOYSA-N 0.000 abstract 1
- IEJIXIDSYBAMLT-UHFFFAOYSA-N gold;1h-imidazole Chemical compound [Au].C1=CNC=N1 IEJIXIDSYBAMLT-UHFFFAOYSA-N 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 239000000413 hydrolysate Substances 0.000 abstract 1
- 238000005580 one pot reaction Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000012876 carrier material Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 241000556626 Blenniidae Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZGURRBATDCNPOD-UHFFFAOYSA-M [Ru].[Cl-].C1(=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical class [Ru].[Cl-].C1(=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 ZGURRBATDCNPOD-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- IXSZQYVWNJNRAL-UHFFFAOYSA-N etoxazole Chemical compound CCOC1=CC(C(C)(C)C)=CC=C1C1N=C(C=2C(=CC=CC=2F)F)OC1 IXSZQYVWNJNRAL-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- SDKPSXWGRWWLKR-UHFFFAOYSA-M sodium;9,10-dioxoanthracene-1-sulfonate Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)[O-] SDKPSXWGRWWLKR-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent 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
- B01J31/22—Organic complexes
-
- 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
-
- 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
- B01J35/64—Pore diameter
- B01J35/647—2-50 nm
-
- 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
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
-
- 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
-
- 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
- B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
- B01J2531/18—Gold
-
- 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
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/821—Ruthenium
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Catalysts (AREA)
Abstract
The invention discloses a method for preparing a gold-ruthenium bimetal supported periodic mesoporous silicon catalyst.The bimetal supported mesoporous silicon material can well disperse in an organic solvent, halogenated benzene acetylene hydrolysis can be carried out by making effective use of low-acidity synergy between imidazole gold salt catalyst and silicon material silicon hydroxyl, and a hydrolysate halogenated benzene ethanone is chirally reduced by using a chiral ruthenium catalyst.Compared with a traditional periodic mesoporous silicon material, the invention provides the bimetal supporting method for this material, cascade reaction of hydrolysis and asymmetric hydrogen transfer can be efficiently finished, the yield is high, and enantioselectivity is good.
Description
Technical field
The present invention relates to catalyst preparation technology, specifically one is applied to synthesis of chiral halogenated aromatic alcohol
The preparation method of the bimetallic periodic mesoporous Si catalyst of gold-supported-ruthenium.
Background technology
Since the order mesoporous silica-base materials of C.T.Kresge reported first in 1992, mesoporous silicon sill because of
One of performance focus being always scientific research of its excellence, the most in recent years since, various forms
Mesoporous silicon sill be constantly in the news, its application is also constantly being expanded.This kind of material
Have that the arrangement degree of order is high, pore diameter range advantage such as controllable in 2-50nm, in electronic information, life
There are extremely important research and using value in the fields such as thing medicine, environment, chemistry, the energy.(C.T.
Kresge.et al.,Nature,1992,359,710-712.M.Jaroniec.et al.,J.Am.Chem.Soc.
2005,127,60-61.B.Hatton.,et al.,Acc.Chem.Res.2005,38:305-312.F.
Hoffmann.,et al.,Angew.Chem.Int.Ed.2006,45:3216-3251.)
One pot of series process is that one has promising methodology of organic synthesis very much.In one pot of cascade reaction
Multistep reaction, can directly obtain without the separation of intermediate from the relatively easy raw material being easy to get
Baroque target molecule.But the key condition that restriction " one kettle way " uses is that requirement is each individually
Step between reaction has compatibility, i.e. will not influence each other.Wherein homogeneous Catalyzed by Pt/M Bimetallic Nano
React owing to its interference each other is difficulty with in one pot of cascade reaction.(A.Zanardi,E.
Peris,et al.,J.Am.Chem.Soc.2009,131,14531–14537；S.Gonell,M.Poyatos,
et al.,Organometallics 2012,31,5606-5614.)
In sum, the porous of mesoporous silicon material, the particularity such as bigger serface and hydrophobicity thereof are utilized
Can, the functional mesoporous silicon materials of design and assembly energy supported bi-metallic, can weaken bimetallic effectively
Interfere, can reduce again and use the environmental pollution that causes of homogeneous catalyst, it is achieved Green Chemistry.
Therefore, the application in one pot of cascade reaction of the mesoporous silicon material of research supported bi-metallic, will have non-
The most important meaning and the prospect of application.
In consideration of it, design becomes with the mesoporous silicon catalyst of the bimetallic functionalization preparing ordered mesopore structure
For the patent technical issues that need to address of the present invention.
Summary of the invention
It is an object of the invention to provide this kind of application and preparation in synthesis of chiral halogenated aromatic alcohol
The method of the bimetallic periodic mesoporous Si catalyst of gold-supported-ruthenium.
Solve the problems referred to above and have a following approach:
The present invention takes the method for silicon source copolymerization to synthesize a kind of periodic mesoporous silicon materials
(FDU), it is specially first by tetraethyl orthosilicate (TEOS), polyoxypropylene polyoxy second
Alkene copolymer (F127) and (R, R)-4-(trimethoxymethylsila,e) ethylphenyl sulfonyl
-1,2-diphenyl diamine functionalized silicon source is hydrolyzed altogether under 15 DEG C ± 0.1 DEG C acid condition
Poly-, then it is aged under the conditions of 100 DEG C, then in ethanol and ammonium nitrate, goes template,
Last catalyst carrier being first passed through in anhydrous methylene chloride is coordinated load 1,3,5-front three
Base tetraphenylphosphonium chloride ruthenium dimer catalyst, then load 1 by adsorption by hydrogen bond, 3-pair (2,6-bis--
Isopropyl phenyl) imido azoles-2-gold (I) Tetrafluoroboric acid salt catalyst, final synthesis one load
Gold-ruthenium bimetallic functional type catalyst.
The bimetallic periodic mesoporous Si catalyst of gold-supported-ruthenium prepared by the method for the present invention, it is possible to very
Good dispersion in organic solvent, can effectively utilize imidazoles gold salt catalyst and silicon materials silicone hydroxyl
Weakly acidic synergism carries out halogeno-benzene acetylene hydrolysis, utilizes chiral ruthenium catalyst to produce hydrolysis simultaneously
Thing halo acetophenone carries out chiral reduction.Owing to this periodic mesoporous silicon materials have loaded two kinds of metals,
Therefore it can carry out one pot of sequential catalyst reaction, is applied to the hydrolysis of halogeno-benzene acetylene and asymmetric hydrogen turns
Move the consecutive reaction of reaction, have huge potential at catalytic field.This bimetallic support type mesoporous silicon material
Expecting that silicon materials periodic mesoporous with tradition are compared, the present invention completes a kind of bimetallic to this type of material
Carrying method, it is possible to be efficiently completed the cascade reaction of hydrolysis and asymmetric hydrogen migration, and there is height
Productivity and enantioselectivity.Sign data show, its surface has the duct of 12.5nm,
XRD small-angle diffraction absworption peak reflects the information of each crystal face the most accurately.
Accompanying drawing explanation
Fig. 1 is the transmission electron microscope (TEM) of catalyst carrier material of the present invention.
Fig. 2 is the transmission electron microscope (TEM) of bimetal supported catalyst of the present invention.
Detailed description of the invention
Provide present pre-ferred embodiments below in conjunction with the accompanying drawings, to describe technical scheme in detail.
Embodiment:
(1) 1.0g polyoxyethylene polyoxypropylene copolymer (F127), 1.2g 1，3，5-trimethyl-benzene, 2.5g are taken
Potassium chloride, 100mL 1mol/L hydrochloric acid solution, it is sequentially added in isothermal reactor, 15 DEG C ± 0.1 DEG C is stirred
Mixing 1 hour, rotating speed is 1200 revs/min.
(2) then drip by 90-95 per minute and be added dropwise over the tetraethyl orthosilicate (TEOS) of 1.875g,
0.5g (R, R)-4-(trimethoxymethylsila,e) ethylphenyl sulfonyl-1,2-diphenyl diamine (uses 0.5mL
Anhydrous methylene chloride dilutes) (two silicon source mol ratios are 9:1), 15 DEG C ± 0.1 DEG C stirring is reacted 24 hours.
(3) transfer to above-mentioned reactant liquor autoclave is aged at 100 DEG C, take after 24 hours
Go out cooling, then carry out sucking filtration, the solid obtained is dried overnight in 60 DEG C of vacuum drying ovens, obtains
A kind of solid of white powder.
(4) weigh the ethanol addition 1500mL's of the above-mentioned product of 2g, 120mg ammonium nitrate, 1000mL
In three-neck flask at 80 DEG C return stirring, carry out sucking filtration after 24 hours, by the solid that obtains in 60 DEG C
Dried in vacuum overnight, the white powdery solids obtained is catalyst carrier material.
(5) 400mg said catalyst carrier material and 40mg 1,3,5-trimethylphenyl ruthenic chloride two are taken
Aggressiveness, 40mL anhydrous methylene chloride is put in 100mL round-bottomed flask, is stirred at room temperature 24 hours, knot
It is spin-dried for solvent after bundle, by the material dichloromethane surname extraction that obtains 4 hours, is dried after terminating
Stand-by.
(6) above-mentioned drying sample is placed in 100mL round-bottomed flask, adds 120mg 1,3-double (2,6-
Two-isopropyl phenyl) imido azoles-2-gold (I) tetrafluoroborate (IPrAuBF4), add 40mL without
Water dichloromethane, stirs 8 hours under room temperature, carries out sucking filtration after stirring, anhydrous with 2mL respectively
Dichloromethane rinses 3 times, and the sample obtained is dried 4 hours in 60 DEG C of vacuum drying ovens, i.e. obtains
Target bimetal supported catalyst.
By Fig. 1 and Fig. 2 it can be seen that gained catalyst surface has the duct of 12.5nm,
XRD small-angle diffraction absworption peak reflects the information of each crystal face the most accurately.
Claims (2)
1. a preparation method for the bimetallic periodic mesoporous Si catalyst of gold-supported-ruthenium, its feature exists
In, first with tetraethyl orthosilicate (TEOS), polyoxyethylene polyoxypropylene copolymer (F127) and
(R, R)-4-(trimethoxymethylsila,e) ethylphenyl sulfonyl-1,2-diphenyl diamine functionalized silicon source exists
Be hydrolyzed under 15 DEG C ± 0.1 DEG C acid condition copolymerization, is then aged under the conditions of 100 DEG C, connects
And go template in ethanol and ammonium nitrate, finally in anhydrous methylene chloride, catalyst carrier is first passed through
Coordination load 1，3，5-trimethyl-benzene base ruthenic chloride dimer catalyst, then load 1,3-by adsorption by hydrogen bond
Double (2,6-bis--isopropyl phenyl) imido azoles-2-gold (I) Tetrafluoroboric acid salt catalyst, final synthesis one load
Gold-ruthenium bimetallic functional type catalyst.
The system of the bimetallic periodic mesoporous Si catalyst of gold-supported-ruthenium the most according to claim 1
Preparation Method, it is characterised in that tetraethyl orthosilicate and (R, R)-4-(trimethoxymethylsila,e) ethylo benzene
The mol ratio in base sulfonyl-1,2-diphenyl diamine functionalized silicon source is 9:1.
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| CN201610143875.6A CN105749977B (en) | 2016-03-14 | 2016-03-14 | A kind of preparation method of the bimetallic periodic mesoporous Si catalyst of gold-supported ruthenium |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106732561A (en) * | 2016-12-31 | 2017-05-31 | 武汉理工大学 | A kind of mesoporous platinum palladium bimetal nano particles and preparation method thereof |
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|---|---|---|---|---|
| US20090036297A1 (en) * | 2005-03-07 | 2009-02-05 | Queen's University At Kingston | Sol Gel Functionalized Silicate Catalyst and Scavenger |
| CN103433074A (en) * | 2013-08-07 | 2013-12-11 | 上海师范大学 | N-(4-toluenesulfonyl)-1,2-diphenyl ethylenediamine functionalized hollow PMO (Periodic Mesoporous Organosilica) catalyst preparation method |
| CN103962152A (en) * | 2014-04-28 | 2014-08-06 | 上海师范大学 | Ru-Pd bi-metal loading chiral catalyst and preparation technology thereof |
-
2016
- 2016-03-14 CN CN201610143875.6A patent/CN105749977B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090036297A1 (en) * | 2005-03-07 | 2009-02-05 | Queen's University At Kingston | Sol Gel Functionalized Silicate Catalyst and Scavenger |
| CN103433074A (en) * | 2013-08-07 | 2013-12-11 | 上海师范大学 | N-(4-toluenesulfonyl)-1,2-diphenyl ethylenediamine functionalized hollow PMO (Periodic Mesoporous Organosilica) catalyst preparation method |
| CN103962152A (en) * | 2014-04-28 | 2014-08-06 | 上海师范大学 | Ru-Pd bi-metal loading chiral catalyst and preparation technology thereof |
Non-Patent Citations (2)
| Title |
|---|
| ALESSANDRO ZANARDI 等: "Well-Defined Ir/Pd Complexes with a Triazolyl-diylidene Bridge as Catalysts for Multiple Tandem Reactions", 《JACS》 * |
| 刘锐 等: "硅基介孔材料负载手性金属催化剂的研究进展", 《上海师范大学学报( 自然科学版)》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106732561A (en) * | 2016-12-31 | 2017-05-31 | 武汉理工大学 | A kind of mesoporous platinum palladium bimetal nano particles and preparation method thereof |
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