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Environment-friendly bionic catalytic nitration method for phenolic compound

A technology of phenolic compounds and compounds, which is applied in the field of green biomimetic catalytic nitration of phenolic compounds, can solve the problems of low product yield, severe conditions, corrosion of equipment, etc., and achieve the effects of reducing environmental pollution, reducing corrosion, and easy operation

Active Publication Date: 2016-10-26
QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to solve the above-mentioned technical problems, the present invention provides a green biomimetic nitration method of phenolic compounds, which overcomes the shortcomings of serious pollution, corroded equipment, severe conditions and low product yield in traditional synthesis methods. The technical scheme adopted is as follows:

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030]At room temperature, dissolve 1mmol of phenol in 40mL of pH=7 phosphate buffer, then add 50mmol of sodium nitrite, dissolve 3mmol of hydrogen peroxide in 10mL of phosphate buffer, drop into the reaction solution within 15min, 0.05 g of Fe-Al-MCM-41 molecular sieve was added to start the reaction, and the reaction was stirred for 80 min. Suction filtration, the filtrate was extracted with ethyl acetate (2×80mL), concentrated under reduced pressure, and separated by column chromatography (filling the column with silica gel, using petroleum ether and acetone as the eluent, the volume ratio of petroleum ether and acetone was 3:1) Promptly obtain target product o-nitrophenol, yield 38.9% ( 1 H NMR (600MHz, DMSO-d 6 )δ10.92(s,1H),7.88(s,1H),7.53(s,1H),7.13(s,1H),6.98(s,1H); 13 C NMR (150MHz, DMSO-d 6 )δ152.52(s), 137.31(s), 135.71(s), 125.59(s), 119.77(s), 119.54(s); HR-ESI-MS m / z: Calcd for C 6 h 4 NO 3 {[M-H] -}:138.0197, found 138.0195), and p-nitrophenol, yield 37.5...

Embodiment 2

[0032] At room temperature, dissolve 1mmol of phenol in 40mL of pH=7 phosphate buffer, then add 60mmol of sodium nitrite, dissolve 3mmol of hydrogen peroxide in 10mL of phosphate buffer, drop into the reaction solution within 15min, Next, 0.06 g of Fe-Al-MCM-41 molecular sieve was added to start the reaction, and the reaction was stirred for 80 min. Suction filtration, the filtrate was extracted with ethyl acetate (2×80mL), concentrated under reduced pressure, and separated by column chromatography (filling the column with silica gel, using petroleum ether and acetone as the eluent, the volume ratio of petroleum ether and acetone was 3:1, Promptly obtain the target product o-nitrophenol, yield 42.0%, and p-nitrophenol, yield 39.8%, total yield 81.8%.Under the same conditions, instead of using molecular sieves, 0.06g uses water-soluble tetra(p-nitrophenol) Sodium sulfonate phenyl) iron porphyrin starts the reaction. As a result, the yield of o-nitrophenol is 27.3%, the yield of...

Embodiment 3

[0034] At room temperature, dissolve 1mmol of phenol in 40mL of pH=7 phosphate buffer, then add 60mmol of sodium nitrite, dissolve 4mmol of hydrogen peroxide in 10mL of phosphate buffer, drop into the reaction solution within 15min, Next, 0.06 g of Fe-Al-MCM-41 molecular sieve was added to start the reaction, and the reaction was stirred for 80 min. Suction filtration, the filtrate was extracted with ethyl acetate (2×80mL), concentrated under reduced pressure, and separated by column chromatography (filling the column with silica gel, using petroleum ether and acetone as the eluent, the volume ratio of petroleum ether and acetone was 3:1, Promptly obtain the target product o-nitrophenol, yield 41.1%, and p-nitrophenol, yield 39.4%, total yield 80.5%.Under the same conditions, instead of using molecular sieves, 0.06g uses water-soluble tetra(p-nitrophenol) Sodium sulfonate phenyl) iron porphyrin starts the reaction. As a result, the yield of o-nitrophenol is 26.9%, the yield of...

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Abstract

The invention discloses an environment-friendly bionic catalytic nitration method for a phenolic compound and belongs to the technical field of organic synthesis. The method provided by the invention comprises the steps of dissolving the phenolic compound, which serves as a raw material, in a solvent at normal temperature, adding sodium nitrite into the solution, then, dropwise adding hydrogen peroxide into the reaction solution, adding metal-doped Al-MCM-41 molecular sieves into the reaction solution at normal temperature so as to start a reaction, carrying out stirring so as to carry out a nitration reaction, and then, carrying out suction filtration, organic solvent extraction, depressurized concentration and column chromatography separation, thereby obtaining a target product. According to the nitration method disclosed by the invention, the reaction conditions are mild, heating is not required, the operation is convenient, and the product is easy to treat. The nitration method is applicable to an environment-friendly bionic catalytic nitration reaction for phenolic compounds.

Description

technical field [0001] The invention relates to a green biomimetic catalytic nitration method for phenolic compounds, belonging to the technical field of organic synthesis. Background technique [0002] The nitration products of phenolic compounds are important fine chemical intermediates, which are widely used in the fields of chemicals, medicine, reagents, etc. important intermediates. At present, the nitration process of phenolic compounds is relatively mature, but each process has certain defects. [0003] The traditional nitration method of phenolic compounds is to use nitric acid or a mixture of nitric acid and sulfuric acid as a nitrating reagent, and react phenols with a nitrating reagent in a general organic solvent to obtain a mixture of nitrophenols, but the selectivity of the reaction is poor. The benzene ring is easily oxidized to quinone compounds, which makes the process difficult to control and the phenolic by-products after nitration are explosive and dang...

Claims

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Application Information

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IPC IPC(8): C07B43/02C07C205/22C07C201/08
CPCC07B43/02C07C201/08C07C205/22
Inventor 孙伟之徐超咸漠刘福胜刘耀杰
Owner QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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