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Method for preparing tetraphenylporphyrin through micro reaction device

A technology of tetraphenylporphyrin and micro-reaction device, which is applied in the direction of organic chemistry, can solve the problems of high reaction temperature, substrate limitation, harsh reaction conditions for synthesizing porphyrin, complex post-treatment, etc., and achieve high-efficiency heat and mass transfer capabilities , easy to directly enlarge, the effect of small reaction volume

Active Publication Date: 2016-07-20
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction temperature is 90-95°C, and the reaction time is 30 hours. The reaction conditions for synthesizing porphyrin are relatively harsh, the time is long, the post-treatment is complicated and the yield is not high, only less than 20%.
The Adler method is an improvement to the Rothemund method. Although it has greatly improved the aforementioned method, it still has too high a reaction temperature and certain substrate limitations in the synthesis, and its yield is also low.

Method used

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  • Method for preparing tetraphenylporphyrin through micro reaction device
  • Method for preparing tetraphenylporphyrin through micro reaction device
  • Method for preparing tetraphenylporphyrin through micro reaction device

Examples

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Effect test

Embodiment 1

[0028] In the microchannel reaction device, the inner diameter of the pipeline in the reactor and the inner diameter of the connecting pipe are both 1mm, the length of the connecting pipe between the feed liquid inlet and the microchannel reactor is 32cm, and the connecting pipe between the microreactor and the feed liquid outlet The length is 30cm; the volume of the microchannel reactor is 10mL; the type of the mixing valve is Y-type.

[0029] Take 0.8mmol of benzaldehyde, 0.8mmol of pyrrole, and 8mmol of absolute ethanol, and add it to 50mL of dichloromethane to make a uniform solution; take 0.32mmol of boron trifluoride ether, add it to 50mL of dichloromethane to make a solution. The two materials are mixed and pumped into the microchannel reactor through the mixing valve. The flow rate of the two pumps is controlled to be 0.167mL / min, and the two streams of materials flow through the microreactor at the same time. In the flask of base benzoquinone, collect 50ml and change...

Embodiment 2

[0031] In the microchannel reaction device, the inner diameter of the pipeline in the reactor and the inner diameter of the connecting pipe are both 0.8mm, the length of the connecting pipe between the feed liquid inlet and the microchannel reactor is 10cm, and the connection between the microreactor and the feed liquid outlet The tube length is 33 cm; the volume of the microchannel reactor is 5 mL; the type of mixing valve is Y type.

[0032] Take 0.8mmol of benzaldehyde, 0.8mmol of pyrrole, and 8mmol of absolute ethanol, and add it to 50mL of dichloromethane to make a uniform solution; take 0.28mmol of boron trifluoride ether, add it to 50mL of dichloromethane to make a solution. The two materials are mixed and pumped into the microchannel reactor through the mixing valve. The flow rate of the two pumps is controlled to be 0.167mL / min, and the two materials flow through the microreactor at the same time. The temperature of the reactor is 30°C, and the reaction residence time...

Embodiment 3

[0034] In the microchannel reaction device, the inner diameter of the pipeline in the reactor and the inner diameter of the connecting pipe are both 1.2mm, the length of the connecting pipe between the feed liquid inlet and the microchannel reactor is 38cm, and the connection between the microreactor and the feed liquid outlet The length of the tube is 25 cm; the volume of the microchannel reactor is 10 mL; the type of the mixing valve is inverted Y.

[0035] Take 1.2mmol of benzaldehyde, 1.2mmol of pyrrole, and 10mmol of absolute ethanol, and add it to 50mL of dichloromethane to make a uniform solution; take 0.32mmol of boron trifluoride ether, and add it to 50mL of dichloromethane to make a solution. The two materials are mixed and pumped into the microchannel reactor through the mixing valve. The flow rate of the two pumps is controlled to be 0.2mL / min, and the two materials flow through the microreactor at the same time. The temperature of the reactor is 30°C, and the reac...

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Abstract

The invention discloses a method for preparing tetraphenylporphyrin through a micro reaction device.The method includes the following steps that 1, benzaldehyde, pyrrole, absolute ethyl alcohol and anhydrous dichloromethane are mixed uniformly to obtain a homogeneous solution A, boron trifluoride diethyl etherate and anhydrous dichloromethane are mixed to obtain a homogeneous solution B; 2, the homogeneous solutions are simultaneously pumped into the micro reaction device; 3, effluent liquid is collected to serve as a crude porphyrinogen product; 4, an oxidizing agent is added into the effluent liquid obtained in the step 3 and stirred to react in nitrogen atmosphere to obtain tetraphenylporphyrin.The method is simple in technology, allows continuous production, short in reaction time, higher in reaction selectivity than conventional reactions and high in operation safety.Meanwhile, the conversion rate is obviously increased to be 50% means of the efficient heat mass transfer capacity and the characteristic of easy direction amplification of the microchannel reactor compared with conventional conditions, and selectivity different from that of conventional reactions can be embodied.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a method for preparing tetraphenylporphyrin by using a micro-reaction device. Background technique [0002] Porphyrin, whose name is transliterated from English "porphyrin", also known as rhodopsin, is a kind of macromolecular heterogeneous compound formed by interconnecting α-carbon atoms of four pyrrole subunits through methine bridges (=CH-). ring compounds. Porphyrin was first proposed by Ktister in 1912, and Fishert and Zeile confirmed the structure in 1929. Its parent is porphine, which is a large π system planar molecule composed of 18 atoms and 18 electrons. There are two active hydrogens on the pyrrole in the porphyrin ring. In living organisms, porphyrin widely exists in cytochrome P-450, heme, chlorophyll and other parts that play an important role in the metabolic process of living organisms, and is called life pigment by scientists. From it...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22
CPCC07D487/22
Inventor 郭凯韩伟李昕黄思宇
Owner NANJING UNIV OF TECH
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