Applying porous organic polymer to epoxidation of olefin on basis of Salen-Mn

A polymer and organic technology, applied in the application field of catalytic olefin epoxidation reaction, can solve the problems of large carrier, poor cycle performance, instability, etc.

Active Publication Date: 2015-08-19
FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, among these two types of methods, the former requires a large amount of carriers, the loading capacity is not high, and the cycle performance is not

Method used

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  • Applying porous organic polymer to epoxidation of olefin on basis of Salen-Mn
  • Applying porous organic polymer to epoxidation of olefin on basis of Salen-Mn
  • Applying porous organic polymer to epoxidation of olefin on basis of Salen-Mn

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0010] Embodiment 1: Mn-POP catalyst

[0011] Add Salen-Mn ligand and s-triynylbenzene into a three-necked flask equipped with a serpentine condenser, and use dry N,N-dimethylformamide as a solvent and dry triethylamine in a nitrogen atmosphere throughout the reaction. As the acid-binding agent, Pd(PPh 3 ) 2 Cl 2 As the main catalyst, CuI was used as the sub-catalyst, and the reaction was refluxed at 90°C for 24 hours. After the reaction is completed, centrifuge, dry in a vacuum oven, extract methanol for 24 hours, and dry in a vacuum oven to obtain the heterogeneous catalyst Mn-POP.

Embodiment 2

[0012] Embodiment 2: Mn-POP catalyst catalyzes olefin epoxidation reaction

[0013] Add cyclohexene, isobutyraldehyde, catalyst Mn-POP respectively in reaction system, the ratio of the amount of substance of the three (wherein Mn-POP takes the content of the metal in the polymer as the amount of substance calculation standard) ratio is 1: 7: 0.001, 1,2-dichloroethane is used as a solvent, the reaction is equipped with a high-efficiency condenser, oxygen is passed into the reaction system in the form of bubbling, the speed is 16ml / min, the reaction temperature is 25°C, after 10 hours of reaction, centrifuge, catalyst Wash with 1,2-dichloroethane, place at room temperature for half an hour, and recycle; the liquid phase part is dried with anhydrous sodium sulfate, and separated by column chromatography to obtain the corresponding olefin epoxidation reaction product.

Embodiment 3

[0014] Embodiment 3: Mn-POP catalyst catalyzes olefin epoxidation reaction

[0015] In reaction system, add cyclooctene, isobutyraldehyde, catalyst Mn-POP respectively, the ratio of the amount of substance of the three (wherein Mn-POP takes the content of the metal in the polymer as the amount of substance calculation standard) ratio is 1: 7: 0.001, 1,2-dichloroethane is used as a solvent, the reaction is equipped with a high-efficiency condenser, oxygen is passed into the reaction system in the form of bubbling, the speed is 16ml / min, the reaction temperature is 25°C, after 10 hours of reaction, centrifuge, catalyst Wash with 1,2-dichloroethane, place at room temperature for half an hour, and recycle; the liquid phase part is dried with anhydrous sodium sulfate, and separated by column chromatography to obtain the corresponding olefin epoxidation reaction product.

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Abstract

The invention relates to a porous organic polymer catalyst and a preparation method thereof, as well as application of porous organic polymer catalyst in epoxidation of olefin. The porous organic polymer catalyst consists of Salen-Mn ligand and 1, 3, 5-acetylenyl benzene, is prepared through Sonogashira-Hagihara coupled reaction, has the advantage of being simple to prepare, and can catalyze the olefin to react with oxygen and isobutyraldehyde to generate epoxidation reaction with relatively high activity and relatively high selectivity. The catalyst can be simply separated from a product, and can be repeatedly used for many times.

Description

technical field [0001] The invention belongs to the technical field of olefin epoxidation catalysts, in particular to a method for preparing a porous organic polymer catalyst Mn-POP synthesized from Salen-Mn, and the application of catalyzing olefin epoxidation reactions. Background technique [0002] Olefin epoxides are active and can undergo ring-opening reactions with a variety of nucleophiles to generate a variety of compounds. Therefore, they are very important synthetic intermediates and are widely used in chemicals, spices, pharmaceuticals, pesticides, etc. field. However, in the process of traditional olefin epoxide production, a variety of by-products will be produced. At the same time, traditional homogeneous catalysts have disadvantages such as difficult separation, easy decomposition, and inability to recycle, which will greatly increase the difficulty and time of product post-processing. Capital investment. Therefore, efforts have been made to solve the above ...

Claims

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Application Information

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IPC IPC(8): B01J31/22C07F13/00C07D301/06C07D303/04
Inventor 刘陶陶曹荣林祖金
Owner FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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