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Schiff base metal catalyst used in liquid phase epoxidation reaction and preparation method of schiff base metal catalyst

A metal catalyst, epoxidation reaction technology, applied in physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, chemical instruments and methods, etc. Alkali ligands are expensive and the active components are easy to dissolve, which can achieve the effects of stable reuse performance, convenient recovery and high activity.

Inactive Publication Date: 2013-09-04
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, Schiff base ligands are usually expensive and the synthesis yields are not high; in addition, most of the currently reported Schiff base catalysts lead to homogeneous catalytic systems, and the catalysts are difficult to recover and reuse.
The traditional solution is to immobilize the Schiff base metal on a porous carrier (such as silica gel, polymer, molecular sieve, etc.) to prepare a supported catalyst, but these methods inevitably increase the mass transfer resistance and the active components are easy to dissolve. The shortcomings that are not easy to overcome

Method used

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  • Schiff base metal catalyst used in liquid phase epoxidation reaction and preparation method of schiff base metal catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Add 150mL of acetonitrile, 6.85g of p-aminobenzoic acid and 6.10g of salicylaldehyde into a 200mL round bottom flask, and stir for 1h at room temperature. The solid was filtered out, and after recrystallization with ethanol, the obtained solid product was dried at 80° C. for 12 hours to obtain 9.8 g of Schiff base ligand (A). Add 4.82 g of the obtained Schiff base ligand and 2.66 g of oxymolybdenum acetylacetonate into 40 mL of acetonitrile solvent, stir at 80°C for 24 hours, filter, wash, and dry at 80°C to obtain the A-molybdenum catalyst. NMR characteristic peaks (300Hz, CDCl 3 )d=7.02(m, 2H), 7.45(m, 3H), 7.70(d, 1H), 8.05(d, 2H), 9.00(s, 1H), 10.45(s, 1H), 12.85(s, 1H ).

[0016] In a 50mL round-bottomed flask equipped with a magnetic stirrer and a spherical condenser, add 0.06g of catalyst A-molybdenum, 15mL of chloroform solvent, 5mmol of cyclooctene and 15mmol of tert-butyl hydroperoxide (TBHP), and heat the water bath to 70°C. Reaction 4h. Then GC analysis ...

Embodiment 2

[0018] Under the situation that the preparation conditions of the catalyst are exactly the same as those in Example 1, only the oxymolybdenum acetylacetonate in the preparation method is replaced with vanadyl acetylacetonate to obtain the catalyst A-vanadium. Catalyst A-vanadium was used for the epoxidation of cyclooctene according to the method described in Example 1, and the olefin conversion rate and product selectivity were both 100%.

Embodiment 3

[0020] Under the situation that the preparation conditions of the catalyst are exactly the same as in Example 1, only the p-aminobenzoic acid in the preparation method is replaced with aniline to obtain the catalyst B-molybdenum. Catalyst B-molybdenum was used in the epoxidation reaction of cyclooctene according to the method described in Example 1, and the olefin conversion rate and product selectivity were both 100%.

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Abstract

The invention relates to a schiff base metal catalyst used in a liquid-phase epoxidation reaction and a preparation method of schiff base metal catalyst, and belongs to the technical field of fine organic chemical industries and catalyst preparation. The schiff base metal catalyst takes salicylaldehyde, an aromatic amine compound and a transition metal compound as raw materials, so that the schiff base metal catalyst containing different metal centers is synthesized, wherein an active component is selected from Mn, Mo, V, Co, Ni and Cu; and the catalytic performance of the schiff base metal catalyst in the liquid-phase epoxidation reaction is provided. An experimental result shows that the catalyst can be used in the epoxidation reaction of multiple olefins, the reaction conditions are mild, and problems of equipment corrosion, polluted wastewater discharge, and the like don't exist. The catalyst has the advantages of high activity and selectivity, simpliness and convenience in recycling and reusability, and is a novel and environment-friendly solid schiff base metal catalyst.

Description

technical field [0001] The invention relates to the preparation and application of a Schiff alkali metal catalyst, in particular to a preparation method of a Salen type Schiff alkali metal catalyst and its application in the epoxidation reaction of an unsaturated carbon-carbon double bond. Background technique [0002] Epoxides are an important class of organic chemical intermediates, widely used in the fields of fine organic synthesis and organic chemicals, and the epoxidation of olefins is an important step in the production of epoxides. In order to overcome the shortcomings and shortcomings of a series of equipment corrosion and high energy consumption caused by the traditional peroxycarboxylic acid method to catalyze olefin epoxidation, in recent years, people have paid more attention to transition metals (such as Mn, Mo , V, Co, Ni, Cu, etc.) as the catalyst, H 2 o 2 , tert-butyl hydroperoxide (TBHP) or O 2 A novel epoxidation catalytic process for oxidants. [0003...

Claims

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Application Information

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IPC IPC(8): B01J31/22C07D301/19C07D303/42C07D303/04
Inventor 冷炎刘建蒋平平
Owner JIANGNAN UNIV
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