CN105032492A - Palladium catalyst supported by magnetic nanoparticles wrapped by porous network polymer and preparation method thereof - Google Patents
Palladium catalyst supported by magnetic nanoparticles wrapped by porous network polymer and preparation method thereof Download PDFInfo
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- CN105032492A CN105032492A CN201510038100.8A CN201510038100A CN105032492A CN 105032492 A CN105032492 A CN 105032492A CN 201510038100 A CN201510038100 A CN 201510038100A CN 105032492 A CN105032492 A CN 105032492A
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Abstract
The invention discloses a palladium catalyst supported by magnetic nanoparticles, which is characterized by being wrapped by a porous network polymer having nitrogen atoms. The supported palladium catalyst is a catalytic active site. The invention has following advantages: (1) the preparation method of the magnetic nanoparticles wrapped by the porous network polymer is easy to carry out and the raw materials are wide in sources, are low in cost and are easy to obtain, so that the preparation method can be used in preparation of large quantity of magnetic supporters and is easy to achieve amplified production; and (2) the magnetic nanoparticles is wrapped by the porous network polymer to form the carrier, wherein the supported palladium nanoparticles are separated by means of the network structure of the polymer, so that the palladium catalyst is good in stability and is high in catalytic activity.
Description
Technical field
The present invention relates to a kind of preparation method and application of holey high polymer coated magnetic nanometer particle load palladium catalyst, relate in particular to and a kind ofly prepare high polymer coated magnetic nanoparticulate carriers by not gram reaction in-situ polymerization and for the method for palladium catalyst load.
Background technology
Suzuki coupling reaction is one of effective means building molecular carbon skeleton in Synthetic Organic Chemistry, although its conventional homogeneous palladium catalysts has, catalytic activity is high, good selective, but homogeneous palladium catalysts difficult separation and recycling, residual palladium catalyst pollutes product, thus limits its range of application.The supported of palladium catalyst can solve its separation and recovery problem, therefore one of study hotspot is in recent years become, but conventional polymer polymer or inorganic compound loaded palladium catalyst need to be separated by centrifugal or filter operation, there is complex operation, problem that separative efficiency is low.
Summary of the invention
The object of the present invention is to provide one method synthesizing magnetic nanometer particle load palladium catalyst easily, described catalyst is not only easy to original position Magneto separate and reclaims, repeatedly recycles, and efficient catalysis Suzuki coupling reaction in a mild condition.
Holey high polymer coated magnetic nanometer particle load palladium catalyst of the present invention, its structural representation is as Fig. 1.
Described carrier is the holey high polymer coated magnetic nano particle with nucleocapsid structure, and its magnetic core is coated with silica or non-coated magnetic Fe
3o
4, γ-Fe
2o
3or NiFe
2o
4nano particle, shell is the holey high polymer with atom N; This magnetic carrier has superparamagnetism.
In the present invention, the synthetic route of catalyst as shown in Figure 2.
A kind of holey high polymer coated magnetic nanometer particle load palladium catalyst, its concrete synthesis comprises the steps:
(1) preparation of holey high polymer coated magnetic nano particle: magnetic nano-particle (gel coated or non-coated magnetic nanometer Fe
3o
4, γ-Fe
2o
3or NiFe
2o
4), anhydrous FeCl
3and dimethoxymethane is scattered in 1,2-dichloroethanes, slowly drip 1,2-dichloroethane solution of porous polymer monomer.After reaction terminates, Magneto separate obtains solid and fully washs with deionized water, absolute ethyl alcohol respectively, removing unconverted monomer, and gained solid, at 60 DEG C of vacuum drying 20-24 hour, obtains holey high polymer coated magnetic nanoparticulate carriers MNPsMPP;
(2) preparation of magnetic nano-particle loaded palladium catalyst: the holey high polymer coated magnetic nanoparticulate carriers MNPsMPP upper step synthesized is distributed in the acetonitrile solution of palladium salt and reacts.Magneto separate obtains loaded palladium catalyst, and is placed on acetone washing in apparatus,Soxhlet's, and to remove the palladium salt of non-load, then dry 20-24 hour under 60 DEG C of vacuum, obtains magnetic nano-particle loaded palladium catalyst MNPsMPP-Pd.
Described in step (1), polymer monomer is aniline or phenylenediamine; Polymer monomer, dimethoxymethane and anhydrous FeCl
3amount of substance than for 1:2 ~ 4:2 ~ 4; Magnetic nano-particle and polymer monomer ingredient proportion are 2 ~ 4mmol (monomer)/g (magnetic nano-particle); First at 40 ~ 50 DEG C of reaction 3 ~ 7h, be then warmed up to 70 ~ 85 DEG C and continue reaction 18 ~ 22h.
Described in step (2), palladium salt is palladium, and reaction temperature is 60 ~ 85 DEG C, and the reaction time is 10 ~ 15h; The palladium content of obtained loaded palladium catalyst is 1.5 ~ 5.3wt%.
Holey high polymer coated magnetic nano particle of the present invention adopts simple and easy to do not gram reaction in-situ polymerization coated, the holey high polymer with active function groups is coated to magnetic nano-particle top layer by one step, complete the modification to magnetic nano-particle, magnetic nano-particle loaded palladium catalyst has superparamagnetism.
The invention has the beneficial effects as follows:
(1) preparation method of holey high polymer coated magnetic nanoparticulate carriers is simple, and raw material sources are wide, cheap and easy to get, can be used for the preparation of a large amount of magnetic carrier, is easy to amplify produce;
(2) with holey high polymer coated magnetic nano particle for carrier, supported palladium nano particle by the network structure interval of polymer, the good stability of loaded palladium catalyst, catalytic activity is high;
(3) loaded palladium catalyst has superparamagnetism, disappear without magnetic during externally-applied magnetic field, can be dispersed in reaction system, when having externally-applied magnetic field, then separated out by rapid precipitation in reaction system and be separated, the original position quick separating being therefore easy to realize palladium catalyst reclaims and recycles;
(4) the Suzuki coupling reaction of loaded palladium catalyst efficiently catalysis halogeno-benzene and aryl boric acid in a mild condition, catalytic activity is close to homogeneous catalyst.
Figure of description
Fig. 1 is the structural representation of holey high polymer coated magnetic nanometer particle load palladium catalyst;
Fig. 2 is the synthetic route of catalyst in the present invention.
Detailed description of the invention
The embodiment of the preparation method of high polymer coated magnetic nano particle is as follows:
Embodiment 1
Magnetic nano-particle (gel coated or non-coated magnetic nanometer Fe is added in flask
3o
4, γ-Fe
2o
3or NiFe
2o
4) 0.8g, anhydrous FeCl
31.2g and 0.6mL dimethoxymethane, 25mL1,2-methylene chloride as solvent, at room temperature drip the 20mL1 of 0.2mL aniline, 2-dichloroethane solution, after dropwising, is warmed up to 45 DEG C, stirring reaction 5h.Then at 80 DEG C, reaction 20h is continued.After reaction terminates, Magneto separate goes out solid, and uses deionized water and absolute ethanol washing respectively, and the vacuum drying one day at 60 DEG C of gained solid, obtains holey polyaniline-coated magnetic nano-particle carrier.
Embodiment 2
Magnetic nano-particle (gel coated or non-coated magnetic nanometer Fe is added in flask
3o
4, γ-Fe
2o
3or NiFe
2o
4) 4g, anhydrous FeCl
38g and 2.3g dimethoxymethane, 100mL1,2-methylene chloride as solvent, at room temperature drip the 80mL1 of 1.1g aniline, 2-dichloroethane solution, after dropwising, is warmed up to 50 DEG C, stirring reaction 5h.Then at 80 DEG C, reaction 20h is continued.After reaction terminates, Magneto separate goes out solid, and uses deionized water and absolute ethanol washing respectively, and the vacuum drying one day at 60 DEG C of gained solid, obtains holey and gather binaphthol coated magnetic nanoparticulate carriers.
Embodiment 3
Magnetic nano-particle (gel coated or non-coated magnetic nanometer Fe is added in flask
3o
4, γ-Fe
2o
3or NiFe
2o
4) 1.0g, anhydrous FeCl
31.5g and 0.6g dimethoxymethane, 30mL1,2-methylene chloride as solvent, at room temperature drip the 30mL1 of 0.3g phenylenediamine, 2-dichloroethane solution, after dropwising, is warmed up to 45 DEG C, stirring reaction 5h.Then at 80 DEG C, reaction 20h is continued.After reaction terminates, Magneto separate goes out solid, and uses deionized water and absolute ethanol washing respectively, and the vacuum drying one day at 60 DEG C of gained solid, obtains holey polyphenyl diamines coated magnetic nanoparticulate carriers.
Embodiment 4
Magnetic nano-particle (gel coated or non-coated magnetic nanometer Fe is added in flask
3o
4, γ-Fe
2o
3or NiFe
2o
4) 3.0g, anhydrous FeCl
35g and 3.0g dimethoxymethane, 80mL1,2-methylene chloride as solvent, at room temperature drip the 50mL1 of 1.0g phenylenediamine, 2-dichloroethane solution, after dropwising, is warmed up to 45 DEG C, stirring reaction 5h.Then at 80 DEG C, reaction 20h is continued.After reaction terminates, Magneto separate goes out solid, and uses deionized water and absolute ethanol washing respectively, and the vacuum drying one day at 60 DEG C of gained solid, obtains holey polyphenyl diamines coated magnetic nanoparticulate carriers.
Preparation method's embodiment of holey high polymer coated magnetic nanometer particle load palladium catalyst is as follows:
Embodiment 5
1.0g holey polyaniline-coated magnetic nano-particle is joined 0.1gPd (OAc)
220mL acetonitrile solution in, 80 DEG C reaction 12h.Product, after Magneto separate, washs 24h with acetone in apparatus,Soxhlet's, and products therefrom dry 24h at 60 DEG C in vacuum drying chamber, obtains loaded palladium catalyst Cat1
Embodiment 6
0.5g holey polyphenyl diamines coated magnetic nano particle is joined 60mgPd (OAc)
215mL acetonitrile solution in, 80 DEG C reaction 12h.Product, after Magneto separate, washs 24h with acetone in apparatus,Soxhlet's, and products therefrom dry 24h at 60 DEG C in vacuum drying chamber, obtains loaded palladium catalyst Cat2.
The application of holey high polymer coated magnetic nanometer particle load palladium catalyst in Suzuki coupling reaction:
In atmosphere, be catalyst with Cat1, in reaction tube, add aryl bromo-derivative 1.0mmol, phenyl boric acid 1.1mmol, K successively
2cO
31.5mmol and 2mL deionized water and 2mL ethanol, Cat1 is the 0.38mol% of aryl bromo-derivative.Reaction temperature is 60
oc, reacts after 1.5 hours, under additional magnetic fields, pours out supernatant, and fully wash Cat1 with ethyl acetate, and merge organic phase, product calculates isolated yield after column chromatography purification.
Aryl bromo-derivative is selected bromobenzene, O-methoxy bromobenzene respectively, to methoxybromobenzene, p bromophenol, o-bromotoluene and 1-naphthols, is carried out six experiments.When aryl is phenyl, the yield of product is higher than 96%, and when aryl is naphthyl, the yield of product also reaches 80%, and in the proper extension reaction time, the yield of product can improve.Reaction result is as shown in table 1.
The yield of table 1. holey polyaniline-coated magnetic nano-particle loaded palladium catalyst Cat1 catalysis Suzuki product
| Sequence number | Aryl bromo-derivative | Product separation productive rate (%) |
| 1 | Bromobenzene | > 99 |
| 2 | O-methoxy bromobenzene | 97 |
| 3 | To methoxybromobenzene | 96 |
| 4 | P bromophenol | 97 |
| 5 | O-bromotoluene | 97 |
| 6 | 1-naphthols | 80 |
The amplification test that Suzuki between Cat1 catalysis bromobenzene and phenyl boric acid reacts
In atmosphere, be catalyst with Cat1, in reaction tube, add bromobenzene 0.3mol, phenyl boric acid 3.3mol, K successively
2cO
30.45mol and 250mL deionized water and 250mL ethanol, Cat1 is 1.27 × 10 of bromobenzene
-3mol%.Reaction temperature is 60
oc, reacts after 1.5 hours, under additional magnetic fields, pours out supernatant, and fully wash Cat1 with ethyl acetate, merge organic phase, product through column chromatography purification, separation yield 98%.
In atmosphere, be catalyst with Cat2, in reaction tube, add bromobenzene 1.0mmol, phenyl boric acid 1.1mmol, K successively
2cO
31.5mmol and 2mL deionized water and 2mL ethanol, Cat3 is the 0.2mol% of bromobenzene.Reaction temperature is 60
oc, reacts after 2.5 hours, under additional magnetic fields, pours out supernatant, and fully wash Cat3 with ethyl acetate, merge organic phase, product through column chromatography purification, separation yield 99%.
Catalyst circulation is tested:
In air atmosphere, take Cat1 as catalyst, reaction temperature is 60
oc, the reaction time is 1.5 hours, n (bromobenzene): n (phenyl boric acid): n (K
2cO
3)=1:1.1:1.5, Cat1 is the 0.38mol% of bromobenzene, and reaction dissolvent is Et
2oH-H
2o (2mL-mL), after reaction terminates, under additional magnetic fields, pours out supernatant, and fully washs Cat1 with ethyl acetate, merges organic phase, column chromatography purification product, calculated yield.Then in reactor, add solvent and reaction substrate, carry out reaction next time.The results are shown in Table 2.
Table 2 holey polyaniline-coated magnetic nano-particle loaded palladium catalyst Cat1 recycles performance
| Recycle number of times | Product yield (%) |
| 1 | > 99 |
| 2 | > 99 |
| 3 | > 99 |
| 4 | 99 |
Holey high polymer coated magnetic nanometer particle load palladium catalyst prepared by the present invention, have high catalytic activity to the Suzuki coupling reaction between multiple phenyl bromo-derivative and phenyl boric acid in a mild condition, product yield is greater than 96%.And this loaded palladium catalyst can reclaim at reaction system situ Magneto separate, continuous circulation uses four catalytic activitys without obvious reduction.
Claims (9)
1. a palladium catalyst for magnetic nano-particle load, it is characterized in that the palladium catalyst of described magnetic nano-particle load adopts the holey high polymer with atom N coated, the palladium catalyst of load is active site, and structural representation is Fig. 1.
2. the palladium catalyst of magnetic nano-particle load according to claim 1, it is characterized in that the palladium catalyst of described magnetic nano-particle load has core-shell structure, its core is the magnetic nano-particle with superparamagnetism, and its shell is the holey high polymer with atom N.
3. holey high polymer coated magnetic nanometer particle load palladium catalyst according to claim 1, is characterized in that described magnetic nano-particle loaded palladium catalyst has superparamagnetism.
4. the preparation method of holey high polymer coated magnetic nanometer particle load palladium catalyst according to claim 1, it is characterized in that, its step is as follows:
(1) preparation of holey high polymer coated magnetic nano particle: magnetic nano-particle, anhydrous FeCl
3and dimethoxymethane is distributed to 1, in 2-dichloroethanes, slowly drip 1,2-dichloroethane solution of porous polymer monomer, at 40 ~ 50 DEG C of reaction 3 ~ 7h, then be warmed up to 70 ~ 85 DEG C and continue reaction 18 ~ 22h, after reaction terminates, Magneto separate obtains the magnetic nano-particle modified, use deionized water, absolute ethanol washing respectively, to remove unconverted monomer, gained solid, at 60 DEG C of vacuum drying 20-24 hour, obtains high polymer coated magnetic nanoparticulate carriers MNPsMPP;
(2) holey high polymer coated magnetic nanoparticulate carriers MNPsMPP is distributed in the acetonitrile solution of palladium reacts, 10 ~ 15h is reacted under the condition of 60 ~ 85 DEG C, Magneto separate obtains loaded palladium catalyst, loaded palladium catalyst is placed in apparatus,Soxhlet's acetone fully to wash, remove the palladium do not loaded on carrier, then dry 20-24 hour under 60 DEG C of vacuum, obtains magnetic nano-particle loaded palladium catalyst MNPsMPP-Pd.
5. the preparation method of holey high polymer coated magnetic nanometer particle load palladium catalyst according to claim 4, is characterized in that in described step (1), polymer monomer is aniline or phenylenediamine.
6. the preparation method of holey high polymer coated magnetic nanometer particle load palladium catalyst according to claim 4, is characterized in that in described step (1), magnetic nano-particle is the magnetic Nano Fe of gel coated
3o
4, γ-Fe
2o
3or NiFe
2o
4.
7. the preparation method of holey high polymer coated magnetic nanometer particle load palladium catalyst according to claim 4, is characterized in that in described step (1), magnetic nano-particle is magnetic Nano Fe
3o
4, γ-Fe
2o
3or NiFe
2o
4.
8. the preparation method of holey high polymer coated magnetic nanometer particle load palladium catalyst according to claim 4, is characterized in that polymer monomer, dimethoxymethane and anhydrous FeCl in described step (1)
3the ratio of amount of substance be 1:2 ~ 4:2 ~ 4; The ratio of magnetic nano-particle and porous polymer monomer is 2 ~ 4mmol porous polymer monomer: 1g magnetic nano-particle.
9. the preparation method of holey high polymer coated magnetic nanometer particle load palladium catalyst according to claim 4, is characterized in that the ratio of holey high polymer coated magnetic nanoparticulate carriers and palladium described in described step (2) is 0.3 ~ 0.6mmol palladium: 1g holey high polymer coated magnetic nanoparticulate carriers.
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| CN110152683A (en) * | 2019-05-27 | 2019-08-23 | 西北工业大学 | One kind can rotation magnetic nano chain supported palladium nano-particle catalyst and preparation method thereof |
| CN110180587A (en) * | 2019-06-28 | 2019-08-30 | 江西省汉高新材料有限公司 | The preparation method and applications of functionalized silicon nanometer sheet loaded palladium catalyst |
| CN110327974A (en) * | 2019-07-26 | 2019-10-15 | 湖北工程学院 | A kind of crosslinking norbornene copolymer/carbon black three-dimensional network supported palladium nanocatalyst and the preparation method and application thereof |
| CN110437448A (en) * | 2019-08-13 | 2019-11-12 | 青岛科技大学 | The method that a kind of ring-opening polymerisation of cyclosiloxane original position prepares magnetic silicon rubber nanocomposite |
| CN116023936A (en) * | 2022-11-16 | 2023-04-28 | 齐鲁工业大学 | Preparation method of netlike nano aggregate and application of netlike nano aggregate in photocatalysis field |
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Cited By (8)
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| CN110152683A (en) * | 2019-05-27 | 2019-08-23 | 西北工业大学 | One kind can rotation magnetic nano chain supported palladium nano-particle catalyst and preparation method thereof |
| CN110152683B (en) * | 2019-05-27 | 2022-04-26 | 西北工业大学 | Autorotation magnetic nanochain supported palladium nanoparticle catalyst and preparation method thereof |
| CN110180587A (en) * | 2019-06-28 | 2019-08-30 | 江西省汉高新材料有限公司 | The preparation method and applications of functionalized silicon nanometer sheet loaded palladium catalyst |
| CN110327974A (en) * | 2019-07-26 | 2019-10-15 | 湖北工程学院 | A kind of crosslinking norbornene copolymer/carbon black three-dimensional network supported palladium nanocatalyst and the preparation method and application thereof |
| CN110327974B (en) * | 2019-07-26 | 2022-03-15 | 湖北工程学院 | Cross-linked norbornene copolymer/carbon black three-dimensional network supported palladium nano catalyst and preparation method and application thereof |
| CN110437448A (en) * | 2019-08-13 | 2019-11-12 | 青岛科技大学 | The method that a kind of ring-opening polymerisation of cyclosiloxane original position prepares magnetic silicon rubber nanocomposite |
| CN116023936A (en) * | 2022-11-16 | 2023-04-28 | 齐鲁工业大学 | Preparation method of netlike nano aggregate and application of netlike nano aggregate in photocatalysis field |
| CN116023936B (en) * | 2022-11-16 | 2023-11-10 | 齐鲁工业大学 | Preparation method of netlike nano aggregate and application of netlike nano aggregate in photocatalysis field |
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