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Method for continuously preparing tetraphenyl porphin

A technology of tetraphenylporphine and benzaldehyde, which is applied in the field of continuous preparation of tetraphenylporphine, can solve problems such as difficulty in judging whether the settling tank is full, unrealized continuous material in and out, and large safety hazards of the stirring paddles, etc., to achieve The effect of avoiding the risk of intermittent oxidation operation, avoiding local hot spots, and easy control of reaction conditions

Inactive Publication Date: 2016-06-08
山东有言环保科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This process is essentially that after adding the solvent required for the reaction in batches, the reactant pyrrole and aromatic aldehyde are continuously added to the stirred tank for reaction, which is no different from the batch process of dropping operation, and is still a batch operation process in essence, and Unrealized continuous material in and out
And in the actual operation process, due to the characteristics of the system itself, the color of the reaction solution is completely opaque, and it is difficult to judge whether the settling tank is filled with TPP in actual production
[0013] (3) The height-to-diameter ratio of the stirred reactor used in this method is 20-40:1, and the safety hazards of equipment machinery, especially the stirring paddle, are relatively large
[0015] (5) This method will bring huge operational safety risk when introducing oxygen-containing gas in the continuous operation process

Method used

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  • Method for continuously preparing tetraphenyl porphin
  • Method for continuously preparing tetraphenyl porphin
  • Method for continuously preparing tetraphenyl porphin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] In the first reactor 1, reaction raw material pyrrole and aromatic aldehyde (R 1 = H, R 2 = H, R 3 =H) Feed in solution form, the solvent is propionic acid, the molar concentration of pyrrole is 0.40mol / L, the molar concentration of aromatic aldehyde is 0.40mol / L, the volume flow rate of pyrrole is 1.05ml / min, the aromatic aldehyde of pyrrole and The molar flow ratio is 1:1. The reaction pressure of the first reactor 1 is 0.83MPa, the reaction temperature is 163.5°C, and the residence time is 244s. The oxygen-containing gas in the second reactor 2 is pure oxygen, and its molar flow ratio to the aromatic aldehyde added in the first reactor 1 is 0.075:1, the reaction pressure of the second reactor 2 is 0.8 MPa, and the reaction temperature is 133.5 ℃, the residence time is 235s. The final synthetic yield of the product TPP based on the reactant pyrrole was 63.9%, and the purity was 98.7%.

Embodiment 2

[0058] In the first reactor 1, reaction raw material pyrrole and aromatic aldehyde (R 1 = H, R 2 = H, R 3 =Cl) feeds in solution form, and solvent is the mixture of propionic acid and toluene, and wherein the volume fraction of propionic acid is 70%, and the molar concentration of pyrrole is 0.10mol / L, and the molar concentration of aromatic aldehyde is 0.20mol / L, and pyrrole The volume flow rate is 2.66ml / min, and the molar flow ratio of pyrrole and aromatic aldehyde is 0.5:1. The reaction pressure of the first reactor 1 is 0.73MPa, the reaction temperature is 179.2°C, and the residence time is 96s. The oxygen-containing gas in the second reactor 2 is pure oxygen, and its molar flow ratio with the aromatic aldehyde added in the first reactor 1 is 1:1, the reaction pressure of the second reactor 2 is 0.70MPa, and the reaction temperature is 149.2 ℃, the residence time is 74s. The final synthetic yield of the product TPP based on the reactant pyrrole was 65.9%, and the puri...

Embodiment 3

[0060] In the first reactor 1, reaction raw material pyrrole and aromatic aldehyde (R 1 = H, R 2 = Cl, R 3 =H) Feed in solution form, solvent is the mixture of propionic acid and benzene, wherein the volume fraction of propionic acid is 80%, the molar concentration of pyrrole is 0.60mol / L, the molar concentration of aromatic aldehyde is 0.60mol / L, pyrrole The volume flow rate is 2.39ml / min, and the molar flow ratio of pyrrole and aromatic aldehyde is 1.0:1. The reaction pressure of the first reactor 1 is 0.90 MPa, the reaction temperature is 176.7° C., and the residence time is 107 s. The oxygen-containing gas in the second reactor 2 is air, and the molar flow ratio between it and the aromatic aldehyde added in the first reactor 1 is 0.9:1, the reaction pressure of the second reactor 2 is 0.87MPa, and the reaction temperature is 176.7°C , the residence time is 25s. The final synthetic yield of the product TPP based on the reactant pyrrole was 66.6%, and the purity was 99.1...

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Abstract

The invention discloses a method for continuously preparing tetraphenyl porphin. The method includes the following steps that 1, pyrrole and aromatic aldehyde are continuously added into a first reactor for conducting a reaction, and first reaction liquid is obtained; 2, the first reaction liquid obtained in step (1) and gas containing oxygen are continuously added into a second reactor for conducting a reaction, and second reaction liquid is obtained; 3, the second reaction liquid is cooled, crystallized, filtered and washed, and a tetraphenyl porphin product is obtained. The method has the advantages of being high in yield, high in reaction efficiency, low in energy consumption, safe, environmentally friendly and applicable to industrialization.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a continuous preparation method for tetraphenylporphine. Background technique [0002] The general formula of tetraphenylporphine (hereinafter referred to as TPP) is general formula (II): [0003] [0004] where R 1 , R 2 , R 3 are various substituents, respectively. [0005] TPP is an important luminescent material and a raw material for the synthesis of metalloporphyrins. The Adler method is generally recognized as the best method for the synthesis of tetraphenylporphine. In the laboratory, pyrrole and benzaldehyde are used as reaction raw materials, and TPP is synthesized by reaction in reflux propionic acid (J.Am.Chem.Soc., 1964, 86:3145; J. Org. Chem., 1967, 32:476). However, the yield of TPP calculated by pyrrole obtained by this method is less than 20%, and 5-10% of the impurity dihydrotetraphenylporphine (hereinafter referred to as TPC) having a structu...

Claims

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Application Information

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IPC IPC(8): C07D487/22
CPCC07D487/22
Inventor 王勤波熊振华
Owner 山东有言环保科技有限公司
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