CN103623871A - In situ supported catalyst and preparation method and application thereof - Google Patents
In situ supported catalyst and preparation method and application thereof Download PDFInfo
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- CN103623871A CN103623871A CN201310624389.2A CN201310624389A CN103623871A CN 103623871 A CN103623871 A CN 103623871A CN 201310624389 A CN201310624389 A CN 201310624389A CN 103623871 A CN103623871 A CN 103623871A
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Abstract
The invention discloses an in situ supported catalyst and a preparation method thereof. The catalyst is used for catalyzing Suzuki reaction. The in site supported catalyst comprises zinc oxide, 2-methylimidazole and palladium ion and is prepared through a mechanochemical method. The catalyst is simple to prepare, can be used for catalyzing bromobenzene (and derivatives thereof) and borophenylic acid (and derivatives thereof) with high activity and high selectivity to perform Suzuki reaction, can be separated from the product simply, and can be reused for times.
Description
Technical field
The invention belongs to Suzuki catalysts technical field, be specifically related to a kind of preparation method of original position loaded catalyst and the application of catalysis Suzuki reaction.
Background technology
In palladium catalysis Suzuki coupling reaction, the biphenyl (and derivative) being built by halogenated aryl hydrocarbon and aryl boric acid is important organic synthesis intermediate, is widely used in the fields such as petrochemical industry, fine chemistry industry and organic synthesis.But homogeneous catalyst is difficult to separation, easily the shortcoming such as decomposes, can not recycle, and has limited their extensive use.People attempt to overcome above-mentioned shortcoming by heterogeneousization of homogeneous catalyst for this reason.At present, be generally by this type of catalyst cupport on organic polymer or inorganic carrier.But these class methods need a large amount of carriers, and load capacity is few, and catalyst is easy to slough from carrier, recycles poor effect.And Coordination Polymer is because it is easy to synthesize, there is large specific area, in fields such as catalysis, there is potential using value, become the focus of Recent study.Mechanochemical reaction is Kaolinite Preparation of Catalyst in a large number, and preparation method is simple.
Summary of the invention
The object of the invention is to have proposed to prepare a kind of original position loaded catalyst and application thereof by mechanochemical reaction.
The original position loaded catalyst preparation method that the present invention proposes, its preparation process is as follows:
At room temperature, by zinc oxide, glyoxal ethyline and palladium ion, the amount of substance by certain, reacts 5-60 minute by mechanochemical reaction, then under condition of ice bath, with sodium borohydride, reduce, deionized water, ethanol washing, vacuum drying, obtains original position loaded catalyst.
The original position loaded catalyst catalysis Suzuki reactions steps that the present invention proposes is as follows: in reaction system, add successively original position loaded catalyst Pd/ZIF-8, bromobenzene (and derivative), phenylboric acid (and derivative), the ratio of three's amount of substance is 0.001-0.01:1:2,, solvent deionized water and alcohol mixed solvent, reaction temperature 25-80 ℃, after reaction 1-24h, filter catalyst deionized water, ethanol washing, vacuum drying, recycles; Liquid phase part is extracted with ethyl acetate, anhydrous sodium sulfate drying, and column chromatography for separation obtains corresponding Suzuki product.
Accompanying drawing explanation
Accompanying drawing is gained catalyst transmission electron microscope picture.
The specific embodiment
Embodiment 1: original position loaded catalyst 1
At room temperature by zinc oxide, glyoxal ethyline and palladium ion, press the amount of substance ratio of 1:2:0.001, by mechanochemical reaction, react 30 minutes (MM40030HZ/min), then under condition of ice bath, with sodium borohydride, reduce, deionized water, ethanol washing, vacuum drying, obtains original position loaded catalyst.
Embodiment 2: original position loaded catalyst 2
At room temperature by zinc oxide, glyoxal ethyline and palladium ion, press the amount of substance ratio of 1:2:0.01, by mechanochemical reaction, react 30 minutes (MM40030HZ/min), then under condition of ice bath, with sodium borohydride, reduce, deionized water, ethanol washing, vacuum drying, obtains original position loaded catalyst.
Embodiment 2: original position loaded catalyst catalysis Suzuki reaction
In reaction system, add successively original position loaded catalyst Pd/ZIF-8, bromobenzene (and derivative), phenylboric acid (and derivative), the ratio of three's amount of substance is 0.005:1:2, solvent deionized water and alcohol mixed solvent, 80 ℃ of reaction temperatures, after reaction 6h, filter, catalyst deionized water, ethanol washing, vacuum drying, recycles; Liquid phase part is extracted with ethyl acetate, anhydrous sodium sulfate drying, and column chromatography for separation obtains corresponding Suzuki product.
Embodiment 3: original position loaded catalyst catalysis Suzuki reaction
In reaction system, add successively original position loaded catalyst Pd/ZIF-8, bromobenzene (and derivative), phenylboric acid (and derivative), the ratio of three's amount of substance is 0.001:1:2, solvent deionized water and alcohol mixed solvent, 80 ℃ of reaction temperatures, after reaction 6h, filter, catalyst deionized water, ethanol washing, vacuum drying, recycles; Liquid phase part is extracted with ethyl acetate, anhydrous sodium sulfate drying, and column chromatography for separation obtains corresponding Suzuki product.
Embodiment 4: original position loaded catalyst catalysis Suzuki reaction
In reaction system, add successively original position loaded catalyst Pd/ZIF-8, bromobenzene (and derivative), phenylboric acid (and derivative), the ratio of three's amount of substance is 0.01:1:2,, solvent deionized water and alcohol mixed solvent, 80 ℃ of reaction temperatures, after reaction 6h, filter catalyst deionized water, ethanol washing, vacuum drying, recycles; Liquid phase part is extracted with ethyl acetate, anhydrous sodium sulfate drying, and column chromatography for separation obtains corresponding Suzuki product.
Claims (3)
1. an original position loaded catalyst, is characterized in that: described catalyst chemical expression formula is Pd/ZIF-8, wherein: ZIF-8 molecular formula is Zn (MeIM)
2, wherein HMeIM is glyoxal ethyline.
2. the preparation method of catalyst described in claim 1, it is characterized in that: concrete steps are as follows: at room temperature by zinc oxide, glyoxal ethyline and palladium ion, by certain amount of substance, by mechanochemical reaction, react 5-60 minute, then under condition of ice bath, with sodium borohydride, reduce, deionized water, ethanol washing, vacuum drying, obtains original position loaded catalyst.
3. catalyst claimed in claim 1 is applied to catalysis bromine benzene and its derivative, the Suzuki reaction of phenylboric acid and derivative thereof.
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Cited By (8)
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| CN104399529A (en) * | 2014-11-18 | 2015-03-11 | 中国石油大学(北京) | Alkadiene selective hydrogenation catalyst as well as preparation method and application thereof |
| CN105633363A (en) * | 2015-12-30 | 2016-06-01 | 哈尔滨工业大学 | Method for preparing hollow porous composite silicon-carbon material |
| CN106622380A (en) * | 2016-12-27 | 2017-05-10 | 五邑大学 | Denitration catalyst and preparation method as well as application of denitration catalyst |
| CN107749483A (en) * | 2017-06-12 | 2018-03-02 | 中国科学技术大学 | A kind of catalyst for hydrogen-air fuel cell cathode material and preparation method thereof |
| CN112237913A (en) * | 2019-07-18 | 2021-01-19 | 中国石油化工股份有限公司 | Preparation method of palladium-based supported hydrogenation catalyst and catalyst thereof |
| CN112675915A (en) * | 2020-12-23 | 2021-04-20 | 泉州师范学院 | Preparation method and application of Pd/ZIF-8 cubic composite material |
| CN114425450A (en) * | 2020-10-13 | 2022-05-03 | 中国石油化工股份有限公司 | Catalyst for preparing unsaturated carbonate, preparation method and application thereof |
| CN116058385A (en) * | 2022-11-18 | 2023-05-05 | 辽宁大学 | Palladium zinc oxide nano enzyme material with double enzyme activities, and preparation method and application thereof |
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104399529A (en) * | 2014-11-18 | 2015-03-11 | 中国石油大学(北京) | Alkadiene selective hydrogenation catalyst as well as preparation method and application thereof |
| CN105633363A (en) * | 2015-12-30 | 2016-06-01 | 哈尔滨工业大学 | Method for preparing hollow porous composite silicon-carbon material |
| CN106622380A (en) * | 2016-12-27 | 2017-05-10 | 五邑大学 | Denitration catalyst and preparation method as well as application of denitration catalyst |
| CN106622380B (en) * | 2016-12-27 | 2019-02-22 | 五邑大学 | A kind of denitrating catalyst and its preparation method and application |
| CN107749483A (en) * | 2017-06-12 | 2018-03-02 | 中国科学技术大学 | A kind of catalyst for hydrogen-air fuel cell cathode material and preparation method thereof |
| CN107749483B (en) * | 2017-06-12 | 2020-05-12 | 中国科学技术大学 | Catalyst for hydrogen-air fuel battery cathode material and preparation method thereof |
| CN112237913A (en) * | 2019-07-18 | 2021-01-19 | 中国石油化工股份有限公司 | Preparation method of palladium-based supported hydrogenation catalyst and catalyst thereof |
| CN112237913B (en) * | 2019-07-18 | 2024-05-03 | 中国石油化工股份有限公司 | Preparation method of palladium supported hydrogenation catalyst and catalyst thereof |
| CN114425450A (en) * | 2020-10-13 | 2022-05-03 | 中国石油化工股份有限公司 | Catalyst for preparing unsaturated carbonate, preparation method and application thereof |
| CN114425450B (en) * | 2020-10-13 | 2023-08-29 | 中国石油化工股份有限公司 | Catalyst for preparing unsaturated carbonate, preparation method and application thereof |
| CN112675915A (en) * | 2020-12-23 | 2021-04-20 | 泉州师范学院 | Preparation method and application of Pd/ZIF-8 cubic composite material |
| CN112675915B (en) * | 2020-12-23 | 2023-01-03 | 泉州师范学院 | Preparation method and application of Pd/ZIF-8 cubic composite material |
| CN116058385A (en) * | 2022-11-18 | 2023-05-05 | 辽宁大学 | Palladium zinc oxide nano enzyme material with double enzyme activities, and preparation method and application thereof |
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Application publication date: 20140312 |