Catalyst for catalyzing oxidation of cyclohexane and preparation method of catalyst

A technology of catalyst and cyclohexane, applied in the direction of physical/chemical process catalyst, organic compound/hydride/coordination complex catalyst, chemical instrument and method, etc., can solve the problem of high catalytic efficiency of porphyrin, and achieve convenient Recovery and recyclability, high catalytic efficiency, high efficiency effect

Inactive Publication Date: 2015-07-29
ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In this invention patent, the porphyrin compound is directly used for catalysis, so that there is no hydrophobic microenvironment similar to the catalytic environment formed by protein chain folding in the bonding position of natural cytochrome P450 around the metalloporphyrin complex, so its The catalytic efficiency is not as high as that of porphyrins immobilized on polymer microspheres

Method used

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  • Catalyst for catalyzing oxidation of cyclohexane and preparation method of catalyst
  • Catalyst for catalyzing oxidation of cyclohexane and preparation method of catalyst
  • Catalyst for catalyzing oxidation of cyclohexane and preparation method of catalyst

Examples

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Effect test

example 1

[0108] (A) Preparation of 5(p-propionate)phenyl-10,15,20-tripyridylporphyrin (EPTPyP):

[0109] React p-hydroxybenzaldehyde, propionic acid, acetic anhydride, pyrrole and 4-pyridine formaldehyde with ethanol, where the mass of p-hydroxybenzaldehyde is used as a benchmark, and 1g of p-hydroxybenzaldehyde requires 100 to 120 mL of propionic acid and 5 to 50 mL of acetic anhydride. 8mL, pyrrole 2~4mL, 4-pyridinecarbaldehyde 2~4mL, ethanol 100~150mL, after standing for 12~18 hours, suction filtration, washing, and column chromatography to obtain 5(p-propionate)phenyl-10, 15,20-tripyridylporphyrin (EPTPyP).

[0110] (B) Preparation of 5(p-hydroxy)phenyl-10,15,20-tripyridylporphyrin (HPTPyP):

[0111] The 5 (p-propionate group) phenyl-10,15,20-tripyridyl porphyrin (EPTPyP) prepared in step (A) is mixed with the methanol solution of chloroform and NaOH and magnetically stirred, and reacted at room temperature After 12 hours, washing with water, centrifugation to remove water and dr...

example 2

[0119] (A) Preparation of 5(p-propionate)phenyl-10,15,20-tripyridylporphyrin (EPTPyP):

[0120] Weigh p-hydroxybenzaldehyde and place it in a reaction vessel, then add propionic acid and acetic anhydride, stir and heat with magnetic force, the reaction temperature is 120-130°C, add pyrrole and 4-pyridine formaldehyde dropwise, heat up to 145-145°C and reflux for 2.5 ~3.5 hours, then cooled to 75~85°C, added ethanol while stirring, left overnight, filtered, washed, and separated by column chromatography to obtain purple crystal 5(p-propionate)phenyl-10,15,20-tri Pyridyl porphyrin: Based on the quality of p-hydroxybenzaldehyde, the volume of propionic acid needed to react 1g of p-hydroxybenzaldehyde is 100-120mL, the volume of acetic anhydride is 5-8mL, and the volume of pyrrole is 2-4mL. The required volume of 4-pyridinecarbaldehyde is 2-4mL, and the required volume of ethanol is 100-150mL; the eluent used for column chromatography separation is a mixture of chloroform and etha...

example 3

[0130] (A) Synthesis of 5-(p-hydroxy)phenyl-10,15,20-tripyridyl porphyrin (MnHPTPyP) coordinated by metal manganese:

[0131] Add 1.386g p-Hydroxybenzaldehyde, 180ml propionic acid, 7ml acetic anhydride in 500ml three-necked bottle, magnetic stirring and heating. The temperature of the oil bath is controlled at about 125°C. 3ml freshly distilled pyrrole and 3ml 4-pyridinecarbaldehyde diluted with 10ml propionic acid were added dropwise with two dropping funnels respectively. After 20 minutes of addition, the solution gradually turns brownish black. Keep stirring, raise the temperature to 140°C and reflux for 3 hours, then evaporate most of the propionic acid and cool to 80°C. 50ml of ethanol was added under stirring and left overnight. Suction filter and wash the crystals with ethanol to obtain dark purple crystals.

[0132] Using a mixed solvent of chloroform and ethanol with a volume ratio of 60:1 as the eluent, the third color band was collected by separation on a silica...

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Abstract

The invention provides a method for preparing a catalyst for catalyzing oxidation of cyclohexane. The method comprises steps as follows: (A), preparing 5 (p-propionate) phenyl-10,15,20-tri(pyridyl) porphyrin; (B), preparing 5(p-hydroxy) phenyl-10,15,20-tri(pyridyl) porphyrin from 5 (p-propionate) phenyl-10,15,20-tri(pyridyl) porphyrin; (C), preparing metallic coordinated 5-(p-hydroxy) phenyl-10,15,20-tri(pyridyl) porphyrin from 5 (p-hydroxy) phenyl-10,15,20-tri(pyridyl) porphyrin; (D), attaching the metallic coordinated 5-(p-hydroxy) phenyl-10,15,20-tri(pyridyl) porphyrin to at least one magnetic microsphere, and methylating 5-(p-hydroxy) phenyl-10,15,20-tri(pyridyl) porphyrin by the aid of methyl iodide.

Description

technical field [0001] The invention relates to a catalyst for catalyzing the oxidation of cyclohexane, in particular to a macromolecule magnetic nanometer catalyst solidly loaded with metal cation porphyrin and its application in catalytic oxidation of cyclohexane. The invention also relates to a preparation method of a polymer magnetic nanometer catalyst loaded with metal cation porphyrin. Background technique [0002] Under mild conditions, the ability of the cytochrome P450 mimic system to catalyze the hydroxylation of the substrate by molecular oxygen is very limited, which is similar to the lack of hydrophobicity formed by protein chain folding in the bonding position of the natural cytochrome P450 around the metalloporphyrin complex related to the microenvironment. In polymer-immobilized metalloporphyrin complexes, the surface groups of the polymer carrier can be used as a chemical simulation of the microenvironment around the enzyme active center, which is expected ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/22C07D487/22
CPCY02P20/50
Inventor 绪连彩张智强赵平陈秀菊董文惠
Owner ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
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