CN105749977B - A kind of preparation method of the bimetallic periodic mesoporous Si catalyst of gold-supported ruthenium - Google Patents
A kind of preparation method of the bimetallic periodic mesoporous Si catalyst of gold-supported ruthenium Download PDFInfo
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- CN105749977B CN105749977B CN201610143875.6A CN201610143875A CN105749977B CN 105749977 B CN105749977 B CN 105749977B CN 201610143875 A CN201610143875 A CN 201610143875A CN 105749977 B CN105749977 B CN 105749977B
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- 239000003054 catalyst Substances 0.000 title claims abstract description 29
- 229910052707 ruthenium Inorganic materials 0.000 title claims abstract description 11
- 230000000737 periodic effect Effects 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 title abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- -1 ethylphenyl sulphonyl 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
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 239000010703 silicon Substances 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 238000007306 functionalization reaction Methods 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 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
- 150000003851 azoles Chemical class 0.000 claims description 3
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 238000007334 copolymerization reaction Methods 0.000 claims description 2
- 238000006471 dimerization reaction Methods 0.000 claims description 2
- 238000001179 sorption measurement Methods 0.000 claims description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 claims 1
- 239000002210 silicon-based material Substances 0.000 abstract description 11
- 239000000463 material Substances 0.000 abstract description 8
- 238000000034 method Methods 0.000 abstract description 7
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract description 4
- 238000010523 cascade reaction Methods 0.000 abstract description 4
- 230000007062 hydrolysis Effects 0.000 abstract description 4
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 4
- UEXCJVNBTNXOEH-UHFFFAOYSA-N phenyl acethylene Natural products C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 abstract description 4
- JAJIPIAHCFBEPI-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O JAJIPIAHCFBEPI-UHFFFAOYSA-N 0.000 abstract description 2
- 230000002378 acidificating effect Effects 0.000 abstract description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract description 2
- 239000000413 hydrolysate Substances 0.000 abstract description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
- 150000002460 imidazoles Chemical class 0.000 abstract description 2
- 238000013508 migration Methods 0.000 abstract description 2
- 230000005012 migration Effects 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 229920001296 polysiloxane Polymers 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000005580 one pot reaction Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- 241000556626 Blenniidae Species 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000013461 design Methods 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000001827 mesitylenyl group Chemical class [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 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
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 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
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006276 transfer reaction 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
- B01J31/22—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
-
- B01J35/647—
-
- 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
Abstract
The invention discloses a kind of preparation method of the bimetallic periodic mesoporous Si catalyst of gold-supported ruthenium, the bimetallic support type mesoporous silicon material can be good at disperseing in organic solvent, imidazoles gold salt catalyst can be effectively utilized and the weakly acidic synergy of silicon materials silicone hydroxyl carries out halo phenylacetylene hydrolysis, while chiral reduction is carried out to hydrolysate halo acetophenone using chiral ruthenium catalyst.Compared with the periodic mesoporous silicon materials of tradition, the present invention completes a kind of bimetallic carrying method to such material, can be efficiently completed the cascade reaction of hydrolysis and asymmetric hydrogen migration, and has high yield and enantioselectivity.
Description
Technical field
The present invention relates to catalyst preparation technology, specifically a kind of gold-supported applied to synthesis of chiral halogenated aromatic alcohol-
The preparation method of the bimetallic periodic mesoporous Si catalyst of ruthenium.
Background technology
Since C.T.Kresge reports order mesoporous silica-base material first within 1992, mesoporous silica-base material is because of its excellent property
Can be always one of focus of scientific research, especially in recent years since, various forms of mesoporous silica-base materials are constantly reported
Road, its application field are also constantly being expanded.This kind of material has aligned orderly degree height, pore diameter range is adjustable in 2-50nm
The advantages that control, there is extremely important research in fields such as electronic information, biological medicine, environment, chemistry, the energy and using valency
Value.(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 kind has promising methodology of organic synthesis very much.Multistep reaction in one pot of cascade reaction can
From raw material relatively simple and easy to get, without the separation of intermediate, to directly obtain baroque target molecule.But restrict
The step of key condition that " one kettle way " uses is between requirement is each individually reacted has compatibility, i.e., will not mutual shadow
Ring.Wherein homogeneous Catalyzed by Pt/M Bimetallic Nano reaction is difficult to realize due to its mutual interference 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 summary, the porous of mesoporous silicon material, the property such as bigger serface and its hydrophobicity, design and assembly are utilized
Can supported bi-metallic functional mesoporous silicon materials, can effectively weaken it is bimetallic interfere, and can is reduced using equal
Environmental pollution caused by phase catalyst, realizes Green Chemistry.Therefore, the mesoporous silicon material of supported bi-metallic is studied in one pot of series connection
Application in reaction, the prospect that will be had very important significance and apply.
In consideration of it, the mesoporous Si catalyst for designing and preparing the bimetallic functionalization of ordered mesopore structure turns into the present invention specially
The sharp technical issues that need to address.
The content of the invention
It is an object of the invention to provide a kind of this application and preparation in gold-supported-ruthenium bimetallic of synthesis of chiral halogenated aromatic alcohol
Periodic mesoporous Si catalyst method.
Solving the above problems has following approach：
The method that the present invention takes silicon source to be copolymerized has synthesized a kind of periodic mesoporous silicon materials (FDU), specially first with just
Tetraethyl orthosilicate (TEOS), polyoxyethylene polyoxypropylene copolymer (F127) and (R, R) -4- (trimethoxymethylsila,e) ethyl
Copolymerization, Ran Hou is hydrolyzed under 15 DEG C of ± 0.1 DEG C of acid conditions in phenyl sulfonyl -1,2- diphenyl diamine functionalization silicon source
It is aged under the conditions of 100 DEG C, template is then gone in ethanol and ammonium nitrate, finally carries catalyst in anhydrous methylene chloride
Body first passes through coordination 1,3,5- trimethylphenyl ruthenic chloride dimerization body catalysts of load, then loads 1,3- pairs by Hydrogen Binding Adsorption
(2,6- bis--isopropyl phenyl) imido azoles -2- gold (I) tetrafluoro boric acid salt catalysts, finally synthesize a kind of gold-supported-ruthenium bimetallic
Functional form catalyst.
The bimetallic periodic mesoporous Si catalyst of gold-supported-ruthenium prepared by the method for the present invention, can be good at disperseing
In organic solvent, imidazoles gold salt catalyst can be effectively utilized and the weakly acidic synergy of silicon materials silicone hydroxyl carries out halogen
Hydrolyzed for phenylacetylene, while chiral reduction is carried out to hydrolysate halo acetophenone using chiral ruthenium catalyst.Due to this week
Phase property mesoporous silicon material has loaded two kinds of metals, therefore it can carry out one pot of sequential catalyst reaction, applied to halo phenylacetylene
Hydrolysis and the consecutive reaction of Asymmetric hydrogen transfer reaction, there is huge potential in catalytic field.The bimetallic support type mesoporous silicon
Material is compared with the periodic mesoporous silicon materials of tradition, and the present invention completes a kind of bimetallic carrying method to such material, energy
The cascade reaction of hydrolysis and asymmetric hydrogen migration is enough efficiently completed, and there is high yield and enantioselectivity.Characterize number
According to showing, its surface has 12.5nm duct, and XRD small-angle diffractions absworption peak also accurately reflects the information of each crystal face.
Brief description of the drawings
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.
Embodiment
Present pre-ferred embodiments are provided below in conjunction with the accompanying drawings, to describe technical scheme in detail.
Embodiment：
(1) 1.0g polyoxyethylene polyoxypropylenes copolymer (F127) is taken, 1.2g 1,3,5- trimethylbenzenes, 2.5g potassium chloride,
100mL 1mol/L hydrochloric acid solutions, are sequentially added in isothermal reactor, 15 DEG C ± 0.1 DEG C stir 1 hour, rotating speed be 1200 turns/
Minute.
(2) 1.875g tetraethyl orthosilicate (TEOS), 0.5g (R, R) -4- and then by 90-95 drops per minute is added dropwise
(trimethoxymethylsila,e) ethylphenyl sulfonyl -1,2- diphenyl diamines (dilute) (two silicon with 0.5mL anhydrous methylene chlorides
Source mol ratio is 9:1), 15 DEG C of ± 0.1 DEG C of stirring reactions 24 hours.
(3) above-mentioned reaction solution is transferred in autoclave and be aged at 100 DEG C, cooling is taken out after 24 hours, then
Filtered, obtained solid is dried overnight in 60 DEG C of vacuum drying chambers, obtains a kind of solid of white powder.
(4) weigh the above-mentioned products of 2g, 120mg ammonium nitrate, 1000mL ethanol add 1500mL three-neck flask in 80
Return stirring at DEG C, filtered, obtained solid is dried in vacuum overnight in 60 DEG C, obtained white powder after 24 hours
Shape solid is catalyst carrier material.
(5) 400mg said catalyst carriers material and the trimethylphenyl ruthenic chloride dimers of 40mg 1,3,5-, 40mL are taken
Anhydrous methylene chloride is put into 100mL round-bottomed flasks, is stirred at room temperature 24 hours, is spin-dried for solvent after terminating, the material that will be obtained
With dichloromethane surname extraction 4 hours, terminate rear dried for standby.
(6) above-mentioned drying sample is placed in 100mL round-bottomed flasks, adds 120mg 1, double (2, the 6- bis--cumenes of 3-
Base) golden (I) tetrafluoroborates (IPrAuBF4) of imido azoles -2-, 40mL anhydrous methylene chlorides are added, are stirred 8 hours at room temperature,
Filtered, rinsed 3 times with 2mL anhydrous methylene chlorides respectively, obtained sample is in 60 DEG C of vacuum drying chambers after stirring
Dry 4 hours, that is, obtain target bimetal supported catalyst.
Gained catalyst surface has 12.5nm duct, XRD small-angle diffraction absworption peaks it can be seen from Fig. 1 and Fig. 2
Accurately reflect the information of each crystal face.
Claims (1)
1. a kind of preparation method of the bimetallic periodic mesoporous Si catalyst of gold-supported-ruthenium, it is characterised in that first with positive silicic acid
Tetra-ethyl ester TEOS, polyoxyethylene polyoxypropylene copolymer F127 and (R, R) -4- (trimethoxymethylsila,e) ethylphenyl sulphonyl
Copolymerization is hydrolyzed under 15 DEG C of ± 0.1 DEG C of acid conditions in base -1,2- diphenyl diamine functionalization silicon source, then in 100 DEG C of bars
It is aged under part, template is then gone in ethanol and ammonium nitrate, is finally first led to catalyst carrier in anhydrous methylene chloride
Cross coordination 1,3,5- trimethylphenyl ruthenic chloride dimerization body catalysts of load, then by Hydrogen Binding Adsorption load 1,3- it is double (2,6- bis--
Isopropyl phenyl) golden (I) the tetrafluoro boric acid salt catalysts of imido azoles -2-, finally synthesize a kind of bimetallic functional form of gold-supported-ruthenium
Catalyst；The tetraethyl orthosilicate and (R, R) -4- (trimethoxymethylsila,e) ethylphenyl sulfonyl -1,2- diphenyl
The mol ratio of diamines functionalization silicon source is 9:1.
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Citations (2)
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|---|---|---|---|---|
| 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 |
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| CA2499782A1 (en) * | 2005-03-07 | 2006-09-07 | Queen's University At Kingston | Sol gel functionalized silicate catalyst and scavenger |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
|---|
| Well-Defined Ir/Pd Complexes with a Triazolyl-diylidene Bridge as Catalysts for Multiple Tandem Reactions;Alessandro Zanardi 等;《JACS》;20090916;第131卷;第14531–14537页 * |
| 硅基介孔材料负载手性金属催化剂的研究进展;刘锐 等;《上海师范大学学报( 自然科学版)》;20130228;第42卷(第1期);第98-105页 * |
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