Microwave assisted process of synthesizing tetraphenyl porphyrin inside ionic liquid

A technology of tetraphenylporphyrin and ionic liquid, applied in chemical instruments and methods, metal/metal oxide/metal hydroxide catalysts, organic chemistry, etc. Long time and other problems, to achieve the effect of good selectivity, simple process, low production cost

Inactive Publication Date: 2009-01-28
LIAONING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional synthesis methods use highly volatile and toxic organic solvents such as pyridine, methanol, xylene, and methylene chloride, and the catalysts used are not easy to recycle and reuse, causing environmental pollution
In addition, the traditional method has long reaction time, difficult separation of products and low yield.

Method used

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  • Microwave assisted process of synthesizing tetraphenyl porphyrin inside ionic liquid
  • Microwave assisted process of synthesizing tetraphenyl porphyrin inside ionic liquid
  • Microwave assisted process of synthesizing tetraphenyl porphyrin inside ionic liquid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] 1.0038g (3×10 -4 mol) silicotungstic acid, 5.8965g (0.026mol) ionic liquid BMIBF 4 , 1.0612g (0.01mol) of benzaldehyde and 0.6709g (0.01mol) of pyrrole were added to a 25mL two-necked round-bottomed flask connected with a condenser tube, and at a microwave power of 600W and a reaction temperature of 160°C, irradiated continuously for 15min, and the reaction mixture became Purple-black viscous liquid, immediately add 100ml of absolute ethanol, let stand for 24h. Suction filtration, the filter cake was washed 3 times with absolute ethanol to remove unreacted reactants. Vacuum drying at 50°C for 24 hours gave a purple solid, which was purified by column chromatography to give a purple crystal. The yield was 64.3%.

Embodiment 2

[0051] 0.2576g (7.7×10 -5 mol) silicotungstic acid, 4.5358g (0.02mol) ionic liquid BMIBF 4 , 1.0612g (0.01mol) of benzaldehyde and 0.3355g (0.005mol) of pyrrole were added to a 25mL two-necked round-bottomed flask connected with a condenser, and the microwave power was fixed at 500W. At a reaction temperature of 150°C, irradiate continuously for 5min. The reaction mixture turned into a purple-black viscous liquid, which was immediately added with 100ml of absolute ethanol and allowed to stand overnight. Suction filtration, the filter cake was washed 3 times with absolute ethanol to remove unreacted reactants. Vacuum-dried at 45°C for 24 hours to obtain a purple solid, which was purified by column chromatography to obtain a purple crystal. The yield was 20.3%.

Embodiment 3

[0053] 1.3384g (4×10 -4 mol) silicotungstic acid, 6.8038g (0.03mol) ionic liquid BMIBF 4 , 1.0612g (0.01mol) of benzaldehyde and 1.0064g (0.015mol) of pyrrole were added to a 25mL two-necked round-bottomed flask connected with a condenser tube, and irradiated continuously for 25min at a microwave power of 800W and a reaction temperature of 190°C. The reaction mixture turned into a purple-black viscous liquid, which was immediately added with 100ml of absolute ethanol and allowed to stand overnight. Suction filtration, the filter cake was washed 3 times with absolute ethanol to remove unreacted reactants. Vacuum drying at 55°C for 30 h gave a purple solid, which was purified by column chromatography to give a purple crystal. The yield was 37.2%.

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PUM

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Abstract

The present invention relates to synthesis of tetraphenyl porphyrin, and is especially microwave assisted process of synthesizing tetraphenyl porphyrin inside ionic liquid. By using ionic liquid as reaction medium and heteropoly acid as catalyst, benzaldehyde and pyrrole are reacted under continuous microwave radiation of 500-800 W power at 150-190 deg.c for 5-25 min, and through further adding anhydrous alcohol, stilling for 24-30 hr, suction filtering, washing filter cake with anhydrous alcohol, and vacuum drying at 45-55 deg.c for 24-30 hr, the purified target product is obtained. The present invention has ionic liquid easily separated and recovered for reuse, short reaction time, low production cost, simple technological process and less environmental pollution.

Description

Technical field: [0001] The invention relates to a method for synthesizing tetraphenylporphyrin. In particular, it relates to the rapid synthesis of tetraphenylporphyrin by using ionic liquid as solvent and microwave radiation method. Background technique: [0002] Tetraphenylporphyrin is one of the most important compounds in porphyrin derivatives. The traditional synthesis method uses highly volatile and toxic organic solvents such as pyridine, methanol, xylene, and methylene chloride, and the catalysts used are not easy to recycle and reuse, causing environmental pollution. In addition, the traditional method has long reaction time, difficult separation of products and low yield. Invention content: [0003] In order to solve the above problems, the present invention provides a method for synthesizing tetraphenylporphyrin by using microwave radiation with ionic liquid as reaction medium and heteropolyacid as catalyst. The method has the advantages of less environmenta...

Claims

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Application Information

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IPC IPC(8): C07D487/22B01J23/30B01J27/188
Inventor 宋溪明吴苹吴秋华王康
Owner LIAONING UNIVERSITY
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