CN102976879B - Supported PtAu catalyst and method for catalytic reduction of olefinic bonds or acetylenic bonds by using same - Google Patents
Supported PtAu catalyst and method for catalytic reduction of olefinic bonds or acetylenic bonds by using same Download PDFInfo
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- CN102976879B CN102976879B CN201210506453.2A CN201210506453A CN102976879B CN 102976879 B CN102976879 B CN 102976879B CN 201210506453 A CN201210506453 A CN 201210506453A CN 102976879 B CN102976879 B CN 102976879B
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- JLBJTVDPSNHSKJ-UHFFFAOYSA-N Cc1ccc(C=C)cc1 Chemical compound Cc1ccc(C=C)cc1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention relates to a supported PtAu catalyst and a method for catalytic reduction of olefinic bonds or acetylenic bonds by using same, and belongs to the technical field of heterogeneous catalysis. The supported PtAu catalyst is prepared by taking platinum acetylacetonate and chloroauric acid tetrahydrate as precursors and active carbon as a carrier, putting the two precursors into n-octadecylamine to prepare a bimetal PtAu through reduction, and loading the obtained bimetal PtAu on the active carbon. According to the method for catalytic reduction of the olefinic bonds or acetylenic bonds by using supported PtAu, halogenated aryl hydrocarbon is used as a substrate, the supported PtAu is used as a catalyst, and under a normal pressure hydrogen atmosphere at room temperature, the substrate and the catalyst are placed into an organic solvent to react so as to selectively reduce the olefinic bonds or acetylenic bonds in substrate molecules. The method has the advantages of simple preparation process of the catalyst, mild reaction condition, high catalyst activity, selectivity and stability and the like, so that highly selective reduction of the olefinic bonds or acetylenic bonds in a series of halogenated aryl hydrocarbon molecules.
Description
Technical field
The present invention relates to the preparation of loading type PtAu and the method for catalytic reduction ethylene linkage or acetylene bond thereof, belong to heterogeneous catalysis technology field.
Background technology
The reduction reaction of unsaturated link(age) (as ethylene linkage, acetylene bond) is one of emphasis of organic synthesis.As a kind of high reactivity commercial catalysts, Pd/C has been widely used in the reduction of ethylene linkage or acetylene bond.But, for the substrate of complicated structure, as when multiple reducible groups such as ethylene linkage (or acetylene bond), halogen and carbonyl coexist in substrate molecule, use business Pd/C to be difficult to the selective reduction realizing ethylene linkage or acetylene bond.Therefore, in implementation structure complex substrate, the high-selectivity reduction of ethylene linkage or acetylene bond has very large challenge.
To this, people mainly have studied following two class catalyst system: one is the heterophasic system that is catalyzer with business Pd/C, need additionally to add sulfur-bearing (as diphenyl sulfide) or nitrogenous (as ammonia, pyridine, 2,2 '-two pyridine etc.) compound (Org.Lett.2006,8,3279-3281; Tetrahedron2006,62,11925-11932), suppress Pd/C active by these additives thus improve the chemical reduction selectivity of ethylene linkage or acetylene bond; Two is the homogeneous systems containing precious metals complex catalyzer.Such as, take sodium-acetate as hydrogen source, rhodium complex is catalyst precursor, the diamines of N-sulfonylation is part, the hydrogen transference hydrogenation (J.Org.Chem.2010,75,2981-2988) of ethylene linkage in a series of substrate molecule can be realized in aqueous phase.And for example, use the complex of iridium of N-heterocycle carbine with large steric hindrance and Phosphine ligands, the high-selectivity reduction (Chem.Commun.2011,47,11653-11655) of ethylene linkage in halogenated aryl hydrocarbon molecule can be realized under room temperature nitrogen atmosphere.For another example, with Cp
2tiCl
2for catalyzer, the Zn powder of reductibility is additive, and triethylamine hydrochloride is proton source, can realize the selective reduction (Org.Lett.2010,12,44-47) of ethylene linkage in some chlorinated aromatic hydrocarbons molecules.But these systems also exist catalyzer and ligand structure complicated difficult with shortcomings such as preparation, less stable, catalyzer or additive usage quantity are larger.
Summary of the invention
The object of this invention is to provide that a kind of Catalyst Preparation Procedures is simple, reaction conditions is gentle, the method for catalyst activity and selectivity and the higher reduction ethylene linkage of stability or acetylene bond.
Technical scheme of the present invention is as follows:
A method for loading type PtAu catalytic reduction ethylene linkage or acetylene bond, is characterized in that the method is carried out as follows:
1) with following structural I, II, III or IV for substrate, with loading type PtAu for catalyzer, under room temperature atmospheric hydrogen atmosphere, substrate and catalyzer are placed in organic solvent react, wherein the volumetric molar concentration of substrate is 0.01 ~ 0.25mol/L, and the volumetric molar concentration of catalyzer is 0.0001 ~ 0.0025mol/L;
Described substrate structure formula is as follows,
Wherein:
R
1be selected from halogen;
R
2be selected from the one in hydrogen, thiazolinyl and alkynyl;
R
3be selected from the one in hydrogen, carbonyl, carboxyl and ester group;
R
4be selected from hydrogen;
2) reaction 4 ~ 24 hours under the state stirred, filtering recovering catalyst, obtains target product to filtrate distillation except desolventizing, or crosses post and be separated and obtain target product.
Organic solvent of the present invention adopts the one in methyl alcohol, ethanol, tetrahydrofuran (THF) and ethyl acetate.
Loading type PtAu catalyzer of the present invention, is characterized in that this catalyzer is prepared as follows:
1) stearylamine is added thermosetting settled solution as solvent, tensio-active agent and reductive agent;
2) continue to be heated to 120 ~ 150
oc, then add methyl ethyl diketone platinum and four hydration hydrochloro-auric acids, wherein the concentration of methyl ethyl diketone platinum and four hydration hydrochloro-auric acids is 0.0022 ~ 0.0066mol/L;
3) continue to be heated to 180 ~ 250
oc, stirs and is cooled to room temperature after 10 ~ 30 minutes, namely obtain bimetal PtAu with after washing with alcohol, then be dispersed in hexanaphthene by the bimetal PtAu obtained;
4) in the hexanaphthene of above-mentioned dispersion bimetal PtAu, gac is added, wherein the mass ratio of bimetal PtAu and gac is 1:20 ~ 1:50, filter after mixture is at room temperature at least stirred 12h, then to filter residue with dry after hexanaphthene washing, namely obtain loading type PtAu.
The nanocrystalline granularity of above-mentioned loading type PtAu catalyzer is 5 ~ 15 nanometers.
The present invention compared with prior art, have the following advantages and high-lighting effect: the inventive method has that Catalyst Preparation Procedures is simple, reaction conditions is gentle, the more high outstanding advantages of catalyst activity, selectivity and stability, avoid the complicated and stable not metal complexes of Structure of need in existing synthetic route, use business Pd/C to need additionally to add the shortcoming such as sulfur-bearing or nitrogenous additive, the high selectivity reduction of ethylene linkage or acetylene bond in halogenated aryl hydrocarbon molecule can be realized in a mild condition.
Accompanying drawing explanation
Fig. 1 is the transmission electron microscope picture of loading type PtAu.
Embodiment
Loading type PtAu catalyzer provided by the invention is prepared as follows:
1) stearylamine is added thermosetting settled solution as solvent, tensio-active agent and reductive agent;
2) continue to be heated to 120 ~ 150
oc, then add methyl ethyl diketone platinum and four hydration hydrochloro-auric acids, wherein the concentration of methyl ethyl diketone platinum and four hydration hydrochloro-auric acids is 0.0022 ~ 0.0066mol/L;
3) continue to be heated to 180 ~ 250
oc, stirs and is cooled to room temperature after 10 ~ 30 minutes, namely obtain bimetal PtAu with after washing with alcohol, then be dispersed in hexanaphthene by the bimetal PtAu obtained;
4) in the hexanaphthene of above-mentioned dispersion bimetal PtAu, gac is added, wherein the mass ratio of bimetal PtAu and gac is 1:20 ~ 1:50, filter after mixture is at room temperature at least stirred 12h, then to filter residue with dry after hexanaphthene washing, namely obtain loading type PtAu; The nanocrystalline granularity of loading type PtAu catalyzer is 5 ~ 15 nanometers.
The method of loading type PtAu catalytic reduction ethylene linkage provided by the present invention or acetylene bond, it carries out as follows:
1) with following structural I or II or III or IV for substrate, with loading type PtAu for catalyzer, under room temperature atmospheric hydrogen atmosphere, substrate and catalyzer are placed in organic solvent react, wherein the volumetric molar concentration of substrate is 0.01 ~ 0.25mol/L, and the volumetric molar concentration of catalyzer is 0.0001 ~ 0.0025mol/L; Described organic solvent is selected from the one in methyl alcohol, ethanol, tetrahydrofuran (THF) and ethyl acetate;
Described substrate structure formula is as follows,
Wherein
R
1be selected from halogen;
R
2be selected from the one in hydrogen, thiazolinyl and alkynyl;
R
3be selected from the one in hydrogen, carbonyl, carboxyl and ester group;
R
4be selected from hydrogen;
2) react 4 ~ 24 hours under the state of stirring, filtering recovering catalyst, except desolventizing or after crossing post separation, target product is obtained to filtrate distillation.
Enumerate embodiment to be below further described the present invention, but the invention is not restricted to following embodiment, under the scope not departing from the described aim in front and back, change is included in technical scope of the present invention.
Embodiment one
Implementation method: continue to be heated to 120 after stearylamine being added thermosetting settled solution
oc, then add 0.066mmol methyl ethyl diketone platinum and 0.066mmol tetra-hydration hydrochloro-auric acid, wherein the concentration of methyl ethyl diketone platinum and four hydration hydrochloro-auric acids is 0.0066mol/L.Mixture is heated to 180
oc, stirs and is cooled to room temperature after 10 minutes, namely obtain bimetal PtAu, disperse with hexanaphthene with after washing with alcohol.Add gac, wherein the mass ratio of bimetal PtAu and gac is 1:50, filters after mixture is at room temperature stirred 48h, then to filter residue with dry after hexanaphthene washing, namely obtain loading type PtAu, wherein the grain fineness number of PtAu nanoparticle is 5nm.
Embodiment two
Implementation method: stearylamine is added thermosetting settled solution as solvent, tensio-active agent and reductive agent.Continue to be heated to 140
oc, then add methyl ethyl diketone platinum and four hydration hydrochloro-auric acids, wherein the concentration of methyl ethyl diketone platinum and four hydration hydrochloro-auric acids is 0.0022mol/L.Continue to be heated to 230
oc, stirs and is cooled to room temperature after 20 minutes, namely obtain bimetal PtAu, be dispersed in hexanaphthene with after washing with alcohol.Then add gac, wherein the mass ratio of bimetal PtAu and gac is 1:20, filters after mixture is at room temperature stirred 12h, then to filter residue with dry after hexanaphthene washing, namely obtain loading type PtAu, wherein the grain fineness number of PtAu nanoparticle is 9nm.
Embodiment three
Implementation method: stearylamine is added thermosetting settled solution as solvent, tensio-active agent and reductive agent.Continue to be heated to 150
oc, then add methyl ethyl diketone platinum and four hydration hydrochloro-auric acids, wherein the concentration of methyl ethyl diketone platinum and four hydration hydrochloro-auric acids is 0.0044mol/L.Continue to be heated to 250
oc, stirs and is cooled to room temperature after 30 minutes, namely obtain bimetal PtAu, be dispersed in hexanaphthene with after washing with alcohol.Add gac, wherein the mass ratio of bimetal PtAu and gac is 1:40, filters after mixture is at room temperature stirred 24h, then to filter residue with dry after hexanaphthene washing, namely obtain loading type PtAu, wherein the grain fineness number of PtAu nanoparticle is 15nm.
Embodiment four
Implementation method: at normal temperatures, is placed in methyl alcohol by 2-bromstyrol and loading type PtAu, and wherein the volumetric molar concentration of substrate is 0.10mol/L, and the volumetric molar concentration of catalyzer is 0.0012mol/L.Add the balloon being full of hydrogen after reactor is airtight, continuously ventilation 3 times, under the state stirred, mixture is reacted 4h at normal temperatures, filtering recovering catalyst, carry out gas chromatography-mass spectrometry analysis to filtrate, productive rate is 86%.
Embodiment five
Implementation method: at normal temperatures, is placed in ethyl acetate by 3-bromstyrol and loading type PtAu, and wherein the volumetric molar concentration of substrate is 0.15mol/L, and the volumetric molar concentration of catalyzer is 0.0009mol/L.Add the balloon being full of hydrogen after reactor is airtight, continuously ventilation 3 times, under the state stirred, mixture is reacted 8h at normal temperatures, filtering recovering catalyst, to filtrate through gas chromatography-mass spectrometry analysis, productive rate is 95%.
Embodiment six
Implementation method: at normal temperatures, is placed in methyl alcohol by 4-bromstyrol and loading type PtAu, and wherein the volumetric molar concentration of substrate is 0.15mol/L, and the volumetric molar concentration of catalyzer is 0.0008mol/L.Add the balloon being full of hydrogen after reactor is airtight, continuously ventilation 3 times, under the state stirred, mixture is reacted 12h at normal temperatures, filtering recovering catalyst, to filtrate through gas chromatography-mass spectrometry analysis, productive rate is 98%.
Embodiment seven
Implementation method: at normal temperatures, is placed in methyl alcohol by 4-bromobenzene acetylene and loading type PtAu, and wherein the volumetric molar concentration of substrate is 0.10mol/L, and the volumetric molar concentration of catalyzer is 0.0015mol/L.Add the balloon being full of hydrogen after reactor is airtight, continuously ventilation 3 times, under the state stirred, mixture is reacted 16h at normal temperatures, filtering recovering catalyst, to filtrate through gas chromatography-mass spectrometry analysis, productive rate is 92%.
Embodiment eight
Implementation method: at normal temperatures, is placed in ethyl acetate by 4-chloro-styrene and loading type PtAu, and wherein the volumetric molar concentration of substrate is 0.20mol/L, and the volumetric molar concentration of catalyzer is 0.0015mol/L.Add the balloon being full of hydrogen after reactor is airtight, continuously ventilation 3 times, under the state stirred, mixture is reacted 6h at normal temperatures, filtering recovering catalyst, to filtrate through gas chromatography-mass spectrometry analysis, productive rate is 99%.
Embodiment nine
Implementation method: at normal temperatures, is placed in methyl alcohol by 4-chlorobenzene subunit acetone and loading type PtAu, and wherein the volumetric molar concentration of substrate is 0.13mol/L, and the volumetric molar concentration of catalyzer is 0.0015mol/L.Add the balloon being full of hydrogen after reactor is airtight, take a breath 3 times continuously, under the state stirred, mixture is reacted 24h at normal temperatures, filtering recovering catalyst, obtain target product to filtrate distillation except crossing post separation after desolventizing, productive rate is 93%.
Embodiment ten
Implementation method: at normal temperatures, is placed in methyl alcohol by 4-chloro-cinnamic acid methyl esters and loading type PtAu, and wherein the volumetric molar concentration of substrate is 0.25mol/L, and the volumetric molar concentration of catalyzer is 0.0025mol/L.Add the balloon being full of hydrogen after reactor is airtight, take a breath 3 times continuously, under the state stirred, mixture is reacted 20h at normal temperatures, filtering recovering catalyst, obtain target product to filtrate distillation except crossing post separation after desolventizing, productive rate is 98%.
Embodiment 11
Implementation method: at normal temperatures, is placed in tetrahydrofuran (THF) by 4-chloro-cinnamic acid and loading type PtAu, and wherein the volumetric molar concentration of substrate is 0.05mol/L, and the volumetric molar concentration of catalyzer is 0.0005mol/L.Add the balloon being full of hydrogen after reactor is airtight, take a breath 3 times continuously, under the state stirred, mixture is reacted 24h at normal temperatures, filtering recovering catalyst, obtain target product to filtrate distillation except crossing post separation after desolventizing, productive rate is 92%.
Embodiment 12
Implementation method: at normal temperatures, is placed in methyl alcohol by 2,4 dichloro benzene subunit acetone and loading type PtAu, and wherein the volumetric molar concentration of substrate is 0.21mol/L, and the volumetric molar concentration of catalyzer is 0.0021mol/L.Add the balloon being full of hydrogen after reactor is airtight, take a breath 3 times continuously, under the state stirred, mixture is reacted 22h at normal temperatures, filtering recovering catalyst, obtain target product to filtrate distillation except crossing post separation after desolventizing, productive rate is 76%.
Embodiment 13
Implementation method: at normal temperatures, by 5-((the bromo-1H-indol-3-yl of 7-) methylene radical)-3-Methylimidazole quinoline-2,4-diketone and loading type PtAu are placed in ethanol, and wherein the volumetric molar concentration of substrate is 0.01mol/L, and the volumetric molar concentration of catalyzer is 0.0001mol/L.Add the balloon being full of hydrogen after reactor is airtight, take a breath 3 times continuously, under the state stirred, mixture is reacted 24h at normal temperatures, filtering recovering catalyst, obtain target product to filtrate distillation except crossing post separation after desolventizing, productive rate is 81%.
Embodiment 14
Implementation method: at normal temperatures, by 5-((the chloro-1H-indol-3-yl of 7-) methylene radical)-3-Methylimidazole quinoline-2,4-diketone and loading type PtAu are placed in ethanol, and wherein the volumetric molar concentration of substrate is 0.02mol/L, and the volumetric molar concentration of catalyzer is 0.0002mol/L.Add the balloon being full of hydrogen after reactor is airtight, take a breath 3 times continuously, under the state stirred, mixture is reacted 24h at normal temperatures, filtering recovering catalyst, obtain target product to filtrate distillation except crossing post separation after desolventizing, productive rate is 88%.
Embodiment 15
Implementation method: at normal temperatures, is placed in methyl alcohol by the own ester of trans-4-bromo-benzoic acid-3-alkene and loading type PtAu, and wherein the volumetric molar concentration of substrate is 0.15mol/L, and the volumetric molar concentration of catalyzer is 0.0015mol/L.Add the balloon being full of hydrogen after reactor is airtight, ventilation 3 times, under the state stirred, reacts mixture to 24h, filtering recovering catalyst at normal temperatures continuously, and obtain target product to filtrate distillation except after desolventizing, productive rate is 99%.
Claims (3)
1. a method for loading type PtAu catalytic reduction ethylene linkage or acetylene bond, is characterized in that the method is carried out as follows:
1) with following structural I, II, III or IV for substrate, with loading type PtAu for catalyzer, under room temperature atmospheric hydrogen atmosphere, substrate and catalyzer are placed in organic solvent react, wherein the volumetric molar concentration of substrate is 0.01 ~ 0.25mol/L, and the volumetric molar concentration of catalyzer is 0.0001 ~ 0.0025mol/L;
Described substrate structure formula is as follows,
Wherein:
R
1be selected from halogen;
R
2be selected from the one in hydrogen, thiazolinyl and alkynyl;
R
3be selected from the one in hydrogen, carboxyl and ester group;
R
4be selected from hydrogen;
2) reaction 4 ~ 24 hours under the state stirred, filtering recovering catalyst, obtains target product to filtrate distillation except desolventizing, or crosses post and be separated and obtain target product;
Described loading type PtAu catalyzer is prepared as follows:
A) stearylamine is added thermosetting settled solution as solvent, tensio-active agent and reductive agent;
B) continue to be heated to 120 ~ 150
oc, then add methyl ethyl diketone platinum and four hydration hydrochloro-auric acids, wherein the concentration of methyl ethyl diketone platinum and four hydration hydrochloro-auric acids is 0.0022 ~ 0.0066mol/L;
C) continue to be heated to 180 ~ 250
oc, stirs and is cooled to room temperature after 10 ~ 30 minutes, namely obtain bimetal PtAu with after washing with alcohol, then be dispersed in hexanaphthene by the bimetal PtAu obtained;
D) in the hexanaphthene of above-mentioned dispersion bimetal PtAu, gac is added, wherein the mass ratio of bimetal PtAu and gac is 1:20 ~ 1:50, filter after mixture is at room temperature at least stirred 12h, then to filter residue with dry after hexanaphthene washing, namely obtain loading type PtAu.
2. the method for loading type PtAu catalytic reduction ethylene linkage as claimed in claim 1 or acetylene bond, is characterized in that, described organic solvent adopts the one in methyl alcohol, ethanol, tetrahydrofuran (THF) and ethyl acetate.
3. the method for loading type PtAu catalytic reduction ethylene linkage as claimed in claim 1 or acetylene bond, it is characterized in that, the nanocrystalline granularity of loading type PtAu catalyzer is 5 ~ 15 nanometers.
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| CN103706377B (en) * | 2013-12-20 | 2015-12-30 | 清华大学 | A kind of acetone hydrogenation produces the platinum based catalyst preparation method of isopropyl alcohol |
| CN104926577B (en) * | 2015-05-05 | 2017-01-11 | 大连理工大学 | Preparation method of substituted cis-olefin |
| CN105727943A (en) * | 2016-01-27 | 2016-07-06 | 清华大学 | Method for synthesizing nano three-way catalyst |
| CN110407681B (en) * | 2019-08-12 | 2023-05-02 | 海南大学 | Dehydrogingerol derivative, preparation method and application thereof |
Citations (2)
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|---|---|---|---|---|
| CN1412164A (en) * | 2001-10-09 | 2003-04-23 | 巴斯福股份公司 | Selective catalytic gas-phase hydrogenation method of chain alkyne, dialkene, chain eneyne hydrocarbon and/or polyene |
| CN102553582A (en) * | 2011-12-01 | 2012-07-11 | 昆明理工大学 | Method for preparing carbon supported Au-Pt or Au-Pd catalyst |
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2012
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1412164A (en) * | 2001-10-09 | 2003-04-23 | 巴斯福股份公司 | Selective catalytic gas-phase hydrogenation method of chain alkyne, dialkene, chain eneyne hydrocarbon and/or polyene |
| CN102553582A (en) * | 2011-12-01 | 2012-07-11 | 昆明理工大学 | Method for preparing carbon supported Au-Pt or Au-Pd catalyst |
Non-Patent Citations (3)
| Title |
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| Characterization of Carbon-Supported AuPt Nanoparticles for Electrocatalytic Methanol Oxidation Reaction;Jin Luo et al.;《Langmuir》;20060214;第22卷(第6期);第2892-2898页 * |
| Enhancement of Pt Utilization in Electrocatalysts by Using Gold Nanoparticles;Dan Zhao et al.;《Angew. Chem. Int. Ed.》;20061231;第45卷;第4955–4959页 * |
| Highly active iridium(I) complexes for the selective hydrogenation of carbon–carbon multiple bonds;Linsey S. Bennie et al.;《Chem.Commun》;20110929;第47卷;第11653–11655页 * |
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