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Method for synthesizing tetraaryl manganese porphyrin through synchronous aldehyde and pyrrole condensation and bivalent manganese salt oxidation insertion reaction

A technology of tetraaryl manganese porphyrin and divalent manganese salt is applied in the field of organic synthesis to achieve the effects of improving condensation yield, simplifying separation process and reducing reaction steps

Pending Publication Date: 2020-08-28
新疆普禾粟新型环保材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] In view of the lack of one-step synthesis of tetraaryl zinc porphyrins from aryl aldehydes, pyrroles and manganese salts in the prior art, metallation reactions from expensive tetraaryl porphyrins and manganese salts or from expensive tetraaryl zinc porphyrins and The defect of tetraaryl manganese porphyrin synthesized by the metal replacement reaction of divalent manganese salt, the purpose of the present invention is to provide a kind of raw material with easy-to-get aryl aldehyde, pyrrole and divalent manganese salt, the condensation of aldehyde and pyrrole And a method for synchronously generating tetraarylmanganese porphyrins with divalent manganese salt oxidative insertion reaction, and obtaining high-purity tetraarylmanganese porphyrins in high yield without using complex separation means, the method is easy to realize industrial production

Method used

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  • Method for synthesizing tetraaryl manganese porphyrin through synchronous aldehyde and pyrrole condensation and bivalent manganese salt oxidation insertion reaction
  • Method for synthesizing tetraaryl manganese porphyrin through synchronous aldehyde and pyrrole condensation and bivalent manganese salt oxidation insertion reaction
  • Method for synthesizing tetraaryl manganese porphyrin through synchronous aldehyde and pyrrole condensation and bivalent manganese salt oxidation insertion reaction

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Experimental program
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Effect test

Embodiment 1

[0030] Add 250mL DMF to a stirred reactor with a reflux condenser, add 0.75 moles of anhydrous aluminum trichloride, 0.5 moles of benzaldehyde, 0.5 moles of pyrrole and 1.5 moles of manganese dichloride successively under stirring, and heat the reaction mixture to reflux After the reaction was maintained for 2 hours, the reaction was stopped, the temperature was lowered, and the mixture was placed at 273K overnight, and the tetraphenylporphyrin manganese purple black crystals were obtained by suction filtration, with a yield of 50%.

Embodiment 2

[0032] Add 240mL DMF to a stirred reactor with a reflux condenser, add 1 mole of anhydrous aluminum trichloride, 0.8 mole of 3-bromopyridine formaldehyde, 0.6 mole of pyrrole and 1.5 mole of manganese dichloride in turn under stirring, and heat to react The mixture was refluxed and maintained for 1 hour, then the reaction was stopped, the temperature was lowered, and it was placed overnight at 273K, and filtered by suction to obtain purple-black crystals of tetrakis(3-bromopyridine)porphyrin manganese, with a yield of 35%.

Embodiment 3

[0034] Add 210mL DMF into a stirred reactor with a reflux condenser, add 1.2 moles of anhydrous aluminum trichloride, 0.8 moles of 2-ethylpyrrole formaldehyde, 0.7 moles of pyrrole and 2 moles of manganese dichloride in turn under stirring, and heat The reaction mixture was refluxed and maintained for 2 hours, then the reaction was stopped, the temperature was lowered, and it was placed at 273K overnight, and filtered by suction to obtain tetrakis(2-ethylpyrrole) porphyrin manganese purple black crystals, with a yield of 30%.

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Abstract

The invention discloses a method for synthesizing tetraaryl manganese porphyrin by synchronous aldehyde and pyrrole condensation and bivalent manganese salt oxidation insertion reaction. Aromatic aldehyde, pyrrole and manganese dichloride are refluxed in a DMF solvent under the catalysis of anhydrous aluminum trichloride to synthesize the tetraaryl manganese porphyrin in one step. The reaction process comprises the following steps: sequentially adding the anhydrous aluminum trichloride, aryl aldehyde, the pyrrole and the manganese dichloride into DMF while stirring, stopping the reaction afterheating reflux reaction for a certain period of time, cooling, standing overnight near 273K, and carrying out suction filtration to obtain porphyrin manganese purple black crystals. According to themethod, the aromatic aldehyde, the pyrrole and the manganese dichloride are directly used as raw materials, porphin is not needed, strongly corrosive organic acid is not used as a solvent, high-puritytetraaryl manganese porphyrin is obtained at a high yield under the condition that a complex separation means is not needed, and industrial production is easy to achieve.

Description

technical field [0001] The invention relates to a method for synchronously synthesizing tetraarylmanganese porphyrins through condensation of aldehydes and pyrrole and oxidative insertion of divalent manganese salts, in particular to a method using aromatic aldehydes, pyrrole and divalent manganese salts as raw materials and using them in DMF solvents The invention discloses a method for synthesizing tetraarylmanganese porphyrin in one step using anhydrous aluminum trichloride as a catalyst, belonging to the field of organic synthesis. Background technique [0002] Manganese porphyrin is a metal-organic compound with a macrocyclic conjugated structure. The ligand porphine of manganese porphyrin is a large ring-shaped molecule composed of 20 carbon atoms and 4 nitrogen atoms, with 4n+2 electrons Stabilizes conjugated systems and aromaticity. In industrial production and life, manganese porphyrin is mainly used as a catalyst for chemical oxidation, electrical and photooxidati...

Claims

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Application Information

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IPC IPC(8): C07F13/00
CPCC07F13/005
Inventor 郭灿城郭欣
Owner 新疆普禾粟新型环保材料有限公司
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