Preparation method and application of Schiff base functionalized ordered mesoporous PMO material solid supported Cu(I) heterogeneous catalyst

A heterogeneous catalyst and functionalization technology, applied in the preparation of organic compounds, physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, etc., can solve metal ion pollution in water, difficult separation and recovery Utilization, limited industrial application prospects, etc., to achieve the effect of easy uniform dispersion, large specific surface area, and good catalytic activity

Inactive Publication Date: 2010-11-10
SHANGHAI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Many works to date have focused on homogeneous organometallic catalysts in aqueous media due to their solubility limitations, and even if they work well, their industrial application prospects are very limited, mainly because they are difficult to separate and recycle from the reaction system. , resulting in increased production costs and pollution of metal ions in water

Method used

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  • Preparation method and application of Schiff base functionalized ordered mesoporous PMO material solid supported Cu(I) heterogeneous catalyst
  • Preparation method and application of Schiff base functionalized ordered mesoporous PMO material solid supported Cu(I) heterogeneous catalyst
  • Preparation method and application of Schiff base functionalized ordered mesoporous PMO material solid supported Cu(I) heterogeneous catalyst

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Experimental program
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Effect test

Embodiment 1

[0027] At room temperature, 1.0 g of amino functionalized ordered mesoporous material PMO(NH 2 -PMO(Et)) (containing N 1.0mmol) was mixed with 10mmol 2-pyridinecarbaldehyde and 20ml ethanol, stirred at room temperature for 15h, then the mixture was filtered, washed, and vacuum-dried overnight at 80°C to obtain ordered mesoporous Schiff base-functionalized PMO(Et) (Schiff base-PMO(Et)). Then take 0.50g Schiffbase-PMO (Et) and add it to 15ml of dimethyl sulfoxide solution containing 0.25mmol CuI (the ratio of Cu and N in the Schiff base functionalized material is 1:2), at room temperature, after stirring for 30h , the solid was filtered and washed with DMSO, ethanol to remove free Cu(I). Finally, the product was dried overnight in a vacuum oven at 80° C. to obtain an ordered mesoporous organometallic copper catalyst.

Embodiment 2

[0029] At room temperature, 0.90 g of amino functionalized ordered mesoporous material PMO(NH 2 -PMO(Et)) (containing N 0.90mmol) was mixed with 0.90mmol 2-pyridinecarbaldehyde and 18ml ethanol, stirred at room temperature for 15h, then the mixture was suction filtered, washed, and dried overnight at 70°C in vacuum to obtain an ordered mediated Schiff base-functionalized PMO(Et) (Schiff base-PMO(Et)). Then take 0.50g Schiffbase-PMO (Et) and add it to 16ml of dimethyl sulfoxide solution containing 0.23mmol CuI (the ratio of Cu and N in the Schiff base functionalized material is 1:2), at room temperature, after stirring for 30h , the solid was filtered and washed with DMSO, ethanol to remove free Cu(I). Finally, the product was dried overnight in a vacuum oven at 80° C. to obtain an ordered mesoporous organometallic copper catalyst.

Embodiment 3

[0031] At room temperature, 1.1 g of amino functionalized ordered mesoporous material PMO(NH 2 -PMO(Et)) (containing N 0.80mmol) was mixed with 0.80mmol 2-pyridinecarbaldehyde and 20ml ethanol, stirred at room temperature for 15h, then the mixture was suction filtered, washed, and vacuum-dried at 80°C overnight to obtain an ordered mediated Schiff base-functionalized PMO(Et) (Schiff base-PMO(Et)). Then take 0.60g Schiffbase-PMO (Et) and add it to 13ml of dimethyl sulfoxide solution containing 0.24mmol CuI (the ratio of Cu and N in the Schiff base functionalized material is 1:2), at room temperature, after stirring for 36h , the solid was filtered and washed with DMSO, ethanol to remove free Cu(I). Finally, the product was dried overnight in a vacuum oven at 80° C. to obtain an ordered mesoporous organometallic copper catalyst.

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Abstract

The invention discloses a method for preparing a Schiff base functionalized ordered mesoporous PMO material solid supported Cu(I) heterogeneous catalyst and application thereof in a Glaser organic reaction in an aqueous medium. The method comprises the following steps of: mixing 0.90 to 1.2g of amino-functionalized PMO with 15 to 25ml of ethanol and 0.8 to 1.2 mmol of 2-pyridylaldehyde solution; stirring the mixture for 12 to 18 hours at room temperature; then filtering and washing the mixture, performing vacuum drying and standing overnight to obtain an ordered mesoporous Schiff base functionalized PMO (Et); adding 0.40 to 0.60g of Schiff base-PMO (Et) into 12 to 18 ml of dimethyl sulfoxide solution which contains 0.1 to 0.3 mmol of CuI; stirring the mixture for 24 to 36 hours at the room temperature; filtering the solids and washing the solids by using the dimethyl sulfoxide and ethanol in turn; and finally performing vacuum drying on the product and standing overnight so as to obtain an ordered mesoporous organic metal copper heterogeneous catalyst. The catalyst has the advantages of organic group content, higher hydrophobic property, easy diffusion of an organic reactant in a pore channel, well contact with a catalytic active site, improvement of catalytic efficiency, ordered mesoporous structure, uniform pore diameter distribution, and large specific surface area.

Description

technical field [0001] The invention relates to a preparation method of a Schiff base functionalized ordered mesoporous PMO material immobilized Cu(I) heterogeneous catalyst and its application in Glaser organic reaction in water medium. Background technique [0002] In recent years, the use of water instead of organic solvents for organic synthesis has become an important branch of green chemistry. Water is the most innocuous substance on earth and the safest solvent, and its application has been significantly developed as an alternative non-polluting solvent for organic reactions. Therefore, it is of great significance to design efficient catalysts for clean organic reactions in aqueous media. Many works to date have focused on homogeneous organometallic catalysts in aqueous media due to their solubility limitations, and even if they work well, their industrial application prospects are very limited, mainly because they are difficult to separate and recycle from the react...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/12B01J35/10C07B37/00C07C2/76C07C15/48C07C15/50C07C43/215C07C41/30C07C22/08C07C17/266
Inventor 朱凤霞杨旭石李和兴张昉
Owner SHANGHAI NORMAL UNIVERSITY
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