Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Green nitrification method and application for phenolic compound

A phenolic compound, green technology, applied in the field of green nitration of phenolic compounds, can solve the problems of serious pollution, corroded equipment, severe conditions, etc., and achieve the effects of reducing environmental pollution, reducing corrosion, and easy operation

Active Publication Date: 2015-10-21
QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
View PDF5 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In order to solve the deficiencies in the prior art, the invention provides a green nitration method of phenolic compounds, which overcomes the shortcomings of serious pollution, corrosion equipment, and severe conditions in the traditional synthesis method. The technical scheme adopted is as follows:

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Green nitrification method and application for phenolic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] 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, Next, 0.05 g of water-soluble tetrakis(p-carboxyphenyl)iron porphyrin was added to start the reaction, and the reaction was stirred for 80 min. Extract with ethyl acetate (2×80mL), concentrate under reduced pressure, and separate by column chromatography (fill the column with silica gel, use petroleum ether and acetone as the eluent, and the volume ratio of petroleum ether and acetone is 3:1) to obtain the target product O-nitrophenol, yield 23.7% ( 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 21.5% ( 1 H NMR ...

Embodiment 2

[0041] 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 water-soluble tetrakis(p-sodium sulfonate phenyl)iron porphyrin was added to start the reaction, and the reaction was stirred for 80 min. Extract with ethyl acetate (2×80mL), concentrate under reduced pressure, and separate by column chromatography (fill the column with silica gel, use petroleum ether and acetone as the eluent, and the volume ratio of petroleum ether and acetone is 3:1 to obtain the target product o-nitrophenol, yield 27.3%, and p-nitrophenol, yield 28.8%.

Embodiment 3

[0043] 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 water-soluble tetrakis(p-sodium sulfonate phenyl)iron porphyrin was added to start the reaction, and the reaction was stirred for 80 min. Extract with ethyl acetate (2×80mL), concentrate under reduced pressure, and separate by column chromatography (fill the column with silica gel, use petroleum ether and acetone as the eluent, and the volume ratio of petroleum ether and acetone is 3:1 to obtain the target product o-nitrophenol, yield 26.9%, and p-nitrophenol, yield 27.8%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a green nitrification method and application for a phenolic compound, belonging to the technical field of organic synthesis. The method provided by the invention comprises the following steps: with the phenolic compound as a raw material, dissolving the phenolic compound into a solvent at room temperature, adding sodium nitrite, then dropwise adding hydrogen peroxide into the obtained reaction solution, adding water-soluble metalloporphyrin at room temperature and starting reaction, carrying out nitrification reaction under stirring, then carrying out extraction by using an organic solvent, and carrying out vacuum concentration and column chromatographic separation so as to obtain a target product. The nitrification method provided by the invention has the advantages of mild reaction conditions, no need of heating, convenient operation and easy treatment of products. The green nitrification reaction is suitable for the phenolic compound.

Description

technical field [0001] The invention relates to a green nitration method and application of phenolic compounds, belonging to the technical field of organic synthesis. Background technique [0002] The nitration products of phenolic compounds are important fine chemical intermediates and are widely used in the fields of medicine and additives. For example, nitrophenol is a widely used acid-base indicator and analytical reagent. An important intermediate for additives and high-energy materials. 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...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C205/22C07C201/08C07B43/02
Inventor 咸漠孙伟之刘耀杰
Owner QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com