A method for synthesizing tetraphenylporphyrin in a reflux tubular reactor

A technology of tubular reactor and tetraphenylporphyrin, which is applied in the direction of organic chemistry, can solve the problems of large amount of catalyst usage, unhandy waste liquid, sticky acidic filtrate, etc., so as to avoid the process of raw material recovery and reduce the use of catalyst Quantity, the effect of reducing production costs

Active Publication Date: 2022-04-19
CHEMVON BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] There are some problems when conventional laboratory equipment and reactors are put into the reaction, such as: the amount of catalyst used in the reaction process is large, resulting in waste; the increase in the three wastes and the poor selectivity of the regional reaction, more dihydroaryl porphyrin impurities are generated; the reaction In the process, because pyrrole is easy to polymerize, the color of the system is dark red, and the acidic filtrate is sticky, the composition is complex, and the waste liquid cannot be treated, etc., the overall reaction yield is also low
[0005] Therefore, for the process scale-up of this product, there are still many difficulties, and it is still necessary to find reaction conditions suitable for industrial scale-up

Method used

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  • A method for synthesizing tetraphenylporphyrin in a reflux tubular reactor
  • A method for synthesizing tetraphenylporphyrin in a reflux tubular reactor

Examples

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Effect test

Embodiment 1

[0033] 1) After the two reaction modules A1 and A2 are connected in parallel with the two reaction modules B and C, the microchannel reactor is replaced with proton acid; benzaldehyde 106g (1mol) and pyrrole 67g (1mol) are mixed into a homogeneous solution and put into the storage tank V-01, the volume is about 170mL; the propionic acid 680g is put into the storage tank V-02, the volume is about 681mL;

[0034] 2) The volume flow rate of the mixed solution of controlled benzaldehyde and pyrrole is 2.0 mL / min preheated by pump P-01 into the first reaction module A1 at 110 °C; the volume flow rate of controlled propionic acid is 7.8 mL / min by pump P-02 into the second reaction module A2 at 120 °C; and then mixed in the third reaction module B At the same time that the mixed material enters the fourth reaction module C, the nitrobenzene 184.5g of the pre-storage tank V-03 is pumped into the pipeline; the delay pipeline of the tube reactor is completed in 3 minutes, and the reaction t...

Embodiment 2

[0039] 1) After the two reaction modules A1 and A2 are paralleled with the two reaction modules of B and C, the microchannel reactor is replaced with proton acid; the benzaldehyde 106g (1mol) and pyrrole 67g (1mol) are mixed into a homogeneous solution and put into the storage tank V-01, the volume is about 170mL; the acetic acid 727g is put into the storage tank V-02, the volume is about 693mL;

[0040] 2) The volume flow rate of the mixed solution of benzaldehyde and pyrrole is controlled by 2.0 mL / min by pump P-01 into the first reaction module A1 to preheat 120 °C; the volume flow rate of controlling acetic acid is 8.2 mL / min by pump P-02 into the second reaction module A2 to preheat 115 °C; and then into the third reaction module B to mix; the compressed air is passed into 80 cm3 / min while the mixed material enters the fourth reaction module C; the delay line of the warp tube reactor, The time is completed in 10min, and the reaction temperature is 125 °C;

[0041] 3) The mate...

Embodiment 3

[0045] 1) After the two reaction modules A1 and A2 are paralleled with the two reaction modules of B and C, the microchannel reactor is replaced with proton acid; the benzaldehyde 106g (1mol) and pyrrole 67g (1mol) are mixed into a homogeneous solution and put into the storage tank V-01, the volume is about 170mL; the acetic anhydride 788g is put into the storage tank V-02, the volume is about 730mL;

[0046] 2) The volume flow rate of the mixed solution of benzaldehyde and pyrrole is controlled by 2.0 mL / min by pump P-01 into the first reaction module A1 to preheat 120 °C; the volume flow rate of controlling acetic anhydride is 9.2 mL / min by pump P-02 into the second reaction module A2 to preheat 115 °C; and then into the third reaction module B to mix; the compressed air is compressed to pass into 30 cm3 / min at the same time as the mixed material enters the fourth reaction module C; the trained tube reactor delays the pipeline. The time is 7min to complete, and the reaction temp...

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Abstract

The invention discloses a method for synthesizing tetraphenylporphyrin in a reflux tubular reactor, that is, benzaldehyde and pyrrole are used in an equimolar ratio under the condition of fluidity, and the reflux tubular reactor is used to deprotonate and deprotonate an acid or anhydride. In the presence of an oxidizing agent, the temperature is controlled at 110-140°C and the pressure is 0-0.2Mpa to synthesize tetraphenylporphyrin through reverse condensation reaction. In the process of the invention, the materials are mixed evenly, the equivalent ratio of the materials in the reaction process is reduced, the amount of catalyst used in the reaction process is reduced, the conversion rate of raw materials and the selectivity of products are all improved, and the occurrence of side reactions and polymerization reactions is reduced. The difficulty of product separation and purification is reduced, and the reaction yield is significantly improved.

Description

Technical field [0001] The present invention relates to the application of a reflux tubular reactor in organic synthesis, specifically to a method of using a reflux tubular reactor for tetraphenylporphyrin reaction, which belongs to the field of organic synthesis. Background [0002] Tetraphenylporphyrin, English name: meso-tetraphenylporphyrine, abbreviated TPP, CAS: 917-23-7, molecular formula C 40 H 33 N 4 , as one of the most important compounds in porphyrin derivatives, it is an important luminescent material, sensitive material, semiconductor material, and its metal complex is widely used in gas sensors, smart materials and sensor technology. [0003] The first porphyrin compounds were extracted from biological weight, and since Hans Fisher's synthesis of iron protoporphyrin IX in 1929 and the Nobel Prize has been awarded, major breakthroughs have been made in the synthesis of porphyrin. However, the synthesis method is based on natural porphyrin compounds as raw materials...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22
CPCC07D487/22
Inventor 薛峰刘洪强
Owner CHEMVON BIOTECH CO LTD
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