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Porous polymer-supported nano-palladium catalyst containing Schiff base structure and its preparation and application in the coupling reaction of haloalkynes to alkyne amines

A technology of structural polymers and coupling reactions, applied in catalytic reactions, organic compound/hydride/coordination complex catalysts, preparation of organic compounds, etc., can solve problems such as limited research and application, instability, etc., to achieve The effect of broad development space, simple and easy method, and large market application value

Active Publication Date: 2021-03-16
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although alkyne amines have a wide range of application values, as a highly charged compound, alkyne amines are very unstable and prone to hydrolysis and oxidation reactions to obtain amides, so the research and application based on alkyne amines has been very limited.

Method used

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  • Porous polymer-supported nano-palladium catalyst containing Schiff base structure and its preparation and application in the coupling reaction of haloalkynes to alkyne amines
  • Porous polymer-supported nano-palladium catalyst containing Schiff base structure and its preparation and application in the coupling reaction of haloalkynes to alkyne amines
  • Porous polymer-supported nano-palladium catalyst containing Schiff base structure and its preparation and application in the coupling reaction of haloalkynes to alkyne amines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1 Preparation of porous polymer-supported nano-palladium catalyst containing Schiff base structure

[0041] In a flask equipped with a condenser and a magnetic stirrer, melamine (MM) (0.313 g, 2.485 mmol), terephthalaldehyde (TPA) (0.5 g, 3.728 mmol) and dimethylsulfoxide (DMSO) ( 15.5ml), after argon bubbling and degassing, react at 180°C for 72h under an inert atmosphere. The off-white powder obtained is a copolymer of melamine and terephthalaldehyde (PMM-TPA).

[0042] Dip 200 mg of the above off-white powder into methanol solution (25 mL) of palladium dichloride (10 mg), stir vigorously for 16 h, centrifuge, wash with methanol, put into methanol solution (20 mL) of sodium borohydride (10 mg), stir vigorously for 16 h, Centrifuge and wash with methanol to obtain a porous polymer-supported nano-palladium catalyst containing a Schiff base structure, with a palladium loading capacity of 1.82%.

Embodiment 2～7

[0044] Adopt the method for embodiment 1 to prepare porous nano-palladium catalyst containing Schiff base structure polymer, difference is to change the mol ratio of TPA and MM and the consumption of palladium chloride when synthesizing PMM-TPA, see Table 1:

[0045] Table 1

[0046] Example serial number The amount of palladium chloride (mg) Molar ratio of TPA to MM in PMM-TPA Palladium load (%) 2 20 PMM-TPA-1.5 4.62 3 40 PMM-TPA-1.5 7.80 4 10 PMM-TPA-0.5 1.45 5 20 PMM-TPA-0.5 2.70 6 10 PMM-TPA-1 6.00 7 20 PMM-TPA-1 7.90

Embodiment 8～10

[0048] The method of Example 1 is adopted to prepare porous nano-palladium catalyst containing Schiff base structure polymer, the difference is to change the diformaldehyde monomer type in the synthetic porous polymer containing Schiff base structure and use ammonium chloropalladate instead of dichloride Palladium, see Table 2:

[0049] Table 2

[0050]

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Abstract

The invention discloses a palladium nanoparticle catalyst supported by a porous polymer containing a Schiff base structure. The catalyst is a compound prepared by subjecting the porous polymer containing the Schiff base structure and divalent palladium ions to coordination at first and then to reduction by a reducing agent, wherein the porous polymer containing the Schiff base structure is a cross-linked copolymer of melamine monomers and dimethanal monomers; palladium nanoparticles account for 0.2 to 25% of the mass of the catalyst; and the sizes of the palladium nanoparticles are in a rangeof 1 to 10 nm. The catalyst provided by the invention is high in catalysis efficiency, and can catalyze the coupling reaction for preparation of alkynylamine from halogenoacetylene without any other inorganic salt reaction aids; and after completion of the reaction, the catalyst can be separated through centrifugation or filtering and cyclically used, so the catalyst is friendly to environment andbetter meets the requirements of sustainable development.

Description

technical field [0001] The invention relates to the technical field of catalyst design, in particular to a porous polymer-supported nano-palladium catalyst containing a Schiff-base structure and a preparation method thereof, and a porous polymer-containing nano-palladium catalyst containing a Schiff-base structure to prepare alkyne-amine coupling in a haloalkyne React application. Background technique [0002] Alkyne amines are very important intermediates in the synthesis of natural products and drugs. The introduction of nitrogen groups on alkynes can change the electrophilicity and lipophilicity of alkynes. In organic synthetic chemistry, alkyne amines provide a new synthetic route for the synthesis of nitrogen-containing drug molecules. Although alkyneamines have a wide range of applications, as a highly charged compound, alkyneamines are very unstable and prone to hydrolysis and oxidation reactions to obtain amides, so the research and application based on alkyneamines...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/06B01J32/00B01J23/44C07C231/12C07C233/09
CPCB01J23/44B01J31/063B01J2231/4277C07C231/12C07C233/09
Inventor 黄家辉史元元王奂
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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