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Production method for tetraphenyl porphin

A technology of tetraphenylporphine and its production method, which is applied in organic chemistry and other fields, and can solve problems such as yield reduction, loss of pyrrole and aromatic aldehyde, and no countermeasures mentioned

Inactive Publication Date: 2015-12-30
山东有言环保科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The application did not realize that the introduction of oxygen-containing solvents into the above-mentioned several solvents during the industrial large-scale continuous operation process would bring huge operational safety risks, and did not mention any countermeasures
At the same time, when the oxygen-containing gas is introduced, the pyrrole and aromatic aldehydes in the system that are too late to react are easily oxidized and lost by oxygen, resulting in a decrease in yield and the generation of colloidal impurities that are difficult to separate

Method used

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  • Production method for tetraphenyl porphin
  • Production method for tetraphenyl porphin
  • Production method for tetraphenyl porphin

Examples

Experimental program
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Effect test

Embodiment 1

[0060] (1) 560mol pyrrole and 560mol benzaldehyde are made into mixed solution, for subsequent use;

[0061] (2) In the 2000L titanium material high-pressure polymerization reactor 1 with mechanical stirring and electric heating jacket, top belt distillation device, add the solvent E that is made up of the cyclohexane of 840L propionic acid and 560L, and from the polymerization reactor 1 Bottom drum into N 2 The oxygen concentration in the gas phase at the outlet of the condenser on the top of the reactor is lower than 1%, and then the electric heating jacket switch of the polymerization reactor 1 is started, the liquid in the polymerization reactor 1 is heated to reflux, and the pressure of the polymerization reactor 1 is maintained at 5.0 atm. At the same time, the mixed solution prepared in step (1) is added dropwise from the top of the polymerization reactor 1, and the molar concentration of pyrrole in the reaction solution is always maintained to be lower than 0.1mol / L du...

Embodiment 2

[0064] Technical process is identical with embodiment 1, difference is:

[0065] (1) add 140mol pyrrole and 280mol p-chlorobenzaldehyde;

[0066] (2) Solvent E is a mixture of 980L propionic acid and 420L toluene;

[0067] (3) The reaction time in the polymerization reactor was 9 minutes, the pressure was controlled at 3 atm, and the temperature was 152.4 ° C when the reaction ended, and the water concentration in the polymerization reactor was controlled to be lower than 0.08% all the time;

[0068] (4) The gas that feeds in the oxidation reactor is pure oxygen, and the reaction time is 18 minutes;

[0069] (5) The crude TPP filter cake is 15.2kg;

[0070] According to this method, the finally obtained solid was vacuum-dried at 80° C. to obtain 12.8 kg of the product TPP, and the amount of pyrrole remaining in the polymerization reaction system was 8.8 mol. The synthesis yield of the product TPP based on the reactant pyrrole is 51.8%, and the purity is 99.5%.

Embodiment 3

[0072] Technical process is identical with embodiment 1, difference is:

[0073] (1) add 840mol pyrrole and 840mol m-chlorobenzaldehyde;

[0074] (2) Solvent E is a mixture of 1120L propionic acid and 280L benzene, the pressure is controlled at 2.8atm, the temperature is 148.8°C at the end of the reaction, and the water concentration in the polymerization reactor is controlled to be lower than 0.04% all the time;

[0075] (3) the reaction time in the polymerization reactor is 12 minutes;

[0076] (4) The gas that feeds in the oxidation reactor is air, and the reaction time is 12 minutes;

[0077] (5) The crude TPP filter cake is 98.7kg;

[0078] According to this method, the finally obtained solid was vacuum-dried at 80° C. to obtain 82.8 kg of product TPP, and the amount of pyrrole remaining in the polymerization reaction system was 48.8 mol. The synthesis yield of the product TPP based on the reactant pyrrole is 55.6%, and the purity is 99.0%.

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Abstract

The invention discloses a production method for tetraphenyl porphin. The production method includes the steps that 1, pyrrole and aromatic aldehyde are prepared into a mixed solution for standby application; 2, solvent is added into a polymerization reactor, the pressure of the polymerization reactor is maintained at 1-5 atm, the mixed solution obtained in the step 1 starts to be dripped to start a polymerization reaction, after the reaction is finished, reaction products are cooled to normal temperature, and filter liquor and a filter cake are obtained through filtration; 3, the filter cake obtained in the step 2 and propionic acid are added into an oxidation reactor, oxygen-containing gas is introduced to carry out an oxidation reaction, cooling is carried out after oxidation is finished, a solid and filter liquor are obtained through filtration, and the solid is washed and dried to obtain the tetraphenyl porphin. The production method has the advantages of being high in yield, safe and environmentally friendly, separation and purification are easy, and the production quality is stable.

Description

technical field [0001] The invention relates to a production method of tetraphenylporphine, in particular to a method for safely and efficiently producing tetraphenylporphine by using pyrrole, aromatic aldehyde and oxygen-containing gas as reaction raw materials. Background technique [0002] Tetraphenylporphine (hereinafter referred to as 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 (J.Am.Chem.Soc. , 1964, 86:3145; J.Org.Chem., 1967, 32:476). However, the yield of TPP calculated by pyrrole is less than 20%, and the impurity dihydrotetraphenylporphine (hereinafter referred to as TPC) is 5-10%. In order to remove the TPC impurities mixed in TPP, subsequent researchers have made a lot of improvements to the Adler method, mainly focus...

Claims

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Application Information

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