Nano palladium supported amphipathic carbon sphere catalyst and application thereof to aqueous-phase Heck reaction

A catalyst and amphiphilic technology, which is used in the field of amphiphilic carbon spheres catalyzing water-phase Heck reaction, can solve the problems of difficult contact between reaction substrates and catalysts, reducing the contact area between non-polar surfaces and water, and difficult for water to contact each other. , to achieve the effect of increased contact area, convenient recycling and low cost

Inactive Publication Date: 2014-09-03
UNIVERSITY OF CHINESE ACADEMY OF SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, for lipophilic substrates in the aqueous phase, it is difficult to contact with water due to the hydrophobic effect, or escape to form a separate phase, or aggregate to reduce the contact area of ​​the non-polar surface and water
Therefore, it is difficult to fully contact the reaction substrate and the catalyst in the aqueous phase, making it difficult to carry out the reaction.

Method used

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  • Nano palladium supported amphipathic carbon sphere catalyst and application thereof to aqueous-phase Heck reaction
  • Nano palladium supported amphipathic carbon sphere catalyst and application thereof to aqueous-phase Heck reaction
  • Nano palladium supported amphipathic carbon sphere catalyst and application thereof to aqueous-phase Heck reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment example 1

[0023] Preparation of Pd / PHCSs catalyst: In a 50ml round bottom flask, 300mg PHCSs, 30mg PdCl 2 Dissolve in 30ml ethanol, heat and stir at reflux for 2h. After the reaction was completed, cool to room temperature, centrifuge, and pour out the ethanol solvent to obtain a gray-black solid. Then, it was centrifugally washed with water (15ml×2) and ethanol (15ml×3), and vacuum-dried at 45° C. for 12 hours to obtain a Pd / PHCSs catalyst. ICP-OES measured that the content of Pd in ​​the catalyst was 4.01wt%.

Embodiment example 2

[0025] Take 1 mmol of iodobenzene and 2 mmol of acrylic acid and add it to 5 ml of deionized water, and add k 2 CO 3 2mmol, Pd / PHCSs catalyst 20mg. The reaction was stirred under reflux for 4h. After the reaction was completed, it was cooled to room temperature, and the product was extracted with diethyl ether (3×10 ml). Both the catalyst and the product are soluble in water under alkaline conditions. Add dilute hydrochloric acid to adjust the pH to acidity, and the product cinnamic acid will be transferred from the water phase to the oil phase, and then separated with a separatory funnel. Anhydrous Na for organic phase 2 SO 4 Dry for 2h. Finally, the organic phase was separated by column chromatography to obtain cinnamic acid with a calculated yield of 91%.

Embodiment example 3

[0027] Take 1 mmol of p-methyl iodobenzene and 2 mmol of acrylic acid into 5 ml of deionized water, and add k 2 CO 3 2mmol, Pd / PHCSs catalyst 20mg. The reaction was stirred under reflux for 4h. After the reaction was completed, it was cooled to room temperature, and the product was extracted with diethyl ether (3×10 ml). Dilute hydrochloric acid was added to adjust the pH to acidity, and the product was transferred from the water phase to the oil phase, and then separated with a separatory funnel. Anhydrous Na for organic phase 2 SO 4 Dry for 2h. Finally, the organic phase was separated by column chromatography to obtain 4-methylcinnamic acid, and the calculated yield was 90%.

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Abstract

The invention belongs to the technical field of green catalysis, and particularly relates to a method for catalyzing an aqueous-phase Heck reaction in the presence of palladium nano particle supported amphipathic carbon spheres. The method is characterized in that the palladium nano particle supported carbon sphere catalyst (Pd/PHCSs) is synthesized in situ by adopting carbon spheres (PHCSs), which are synthesized in a hydrothermal method, as a carrier, PdCl2 as a precursor and ethanol as a solvent and a reduction agent. The catalyst can be applied to the aqueous-phase Heck reaction and is high in catalytic activity; moreover, the synthesis process of the catalyst is simple, and the catalyst is recyclable and is free of environment pollution.

Description

technical field [0001] The invention belongs to the technical field of green catalysis, and in particular relates to a method for catalyzing an aqueous phase Heck reaction using amphiphilic carbon spheres loaded with palladium nanoparticles. Background technique [0002] The Heck reaction refers to the coupling reaction of unsaturated halogenated hydrocarbons and alkenes to generate substituted alkenes under the catalysis of strong base and palladium. It is an important class of reactions for forming carbon-carbon bonds in organic synthesis. In recent decades, the Heck reaction has made important achievements in the field of homogeneous catalysis. In the homogeneous system, the catalyst species of palladium are all dissolved in the reaction system, so that they can fully contact with the reactants and obtain high reactivity and selectivity. However, the large-scale application of palladium catalysts is limited due to the difficulty in separation and recovery of catalysts an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J23/44C07C51/353C07C57/44C07C57/42C07C59/64
CPCY02P20/584
Inventor 周克斌朱志彬
Owner UNIVERSITY OF CHINESE ACADEMY OF SCIENCES
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