Method for preparing nitrocompounds from nitrogen suboxides

A technology of nitro compounds and oxides, which is applied in one field to achieve the effects of improving atom economy, high regioselectivity, and improving selectivity

Inactive Publication Date: 2013-11-20
彭新华
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the basis of the high site selectivity results obtained by the Suzuki research group (Peng X, Suzuki H. Org Lett, 2001, 3, 3431-3434) in the implementation of solid acid-catalyzed nitration of aromatics, the applicant applied zeolite and other aluminosilicates Salt and its modified product catalysts, choose the nitrogen dioxide / ozone method, which can enhance the regioselective control of the preparation of dinitro monocyclic aromatic hydrocarbons, but this method needs to use ozone to activate nitrogen dioxide molecules

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] In the reactor, 0.84 g (10.0 mmol) cyclopentanone, 0.50 g HZSM-5 and 1.00 mL (15.7 mmol) dinitrogen tetroxide were added, and the reaction was stirred for 15 hours at 0.051 MPa and room temperature in an oxygen atmosphere. After the completion of the reaction, oxygen gas was introduced into the reaction mixture at normal pressure until the nitrogen oxides completely escaped from the reactor to the cold trap recovery device, and then 10 g of cyclohexanone was added to the reactor mixture, and the catalyst was filtered out after stirring for a while. The filtrate was washed with 5% (m / m) sodium bicarbonate aqueous solution until it was nearly neutral, and then washed with distilled water until the organic phase was neutral, and concentrated by vacuum rotary evaporation. The content of the product components was analyzed by gas chromatography with nitrobenzene as the internal standard. The mass of 2-nitrocyclopentanone and 3-nitrocyclopentanone is 0.91g, and the yield is 71...

Embodiment 2

[0031] Add 0.94 g (10.0 mmol) of phenol and 0.57 g of HZSM-5 to a reactor equipped with 20 mL of dichloromethane. Under the conditions of 0.011 MPa and magnetic stirring at a temperature of 0 to 5°C, in an atmosphere of nitrogen monoxide and oxygen React for 9 hours. After the reaction is completed, oxygen is introduced into the reaction mixture at atmospheric pressure until the nitrogen oxides completely escape the reactor, and then the catalyst is filtered out. The filtrate was washed with 5% (m / m) sodium bicarbonate aqueous solution until it was nearly neutral, and then washed with distilled water until the organic phase was neutral, and concentrated by vacuum rotary evaporation. The content of the product components was analyzed by gas chromatography with nitrobenzene as the internal standard. The mass of nitrophenol was 1.16 g, and the yield was 83%, of which the mass fraction of 2-nitrophenol was 37%, the mass fraction of 3-nitrophenol was 10%, and the mass fraction of 4...

Embodiment 3

[0033] In a reactor equipped with 20 mL of dichloromethane, 0.68 g (5.6 mmol) of benzoic acid, 0.35 g of SAPO-11 and 1.0 mL of nitrogen dioxide were added, and the reaction was stirred for 15 hours at 0.15 MPa and room temperature in an air atmosphere. After the reaction is completed, oxygen is introduced into the reaction mixture at atmospheric pressure until the nitrogen oxides completely escape to the cold trap reaction receiver, and then the catalyst is filtered out. The filtrate was washed with 5% (m / m) sodium bicarbonate aqueous solution until it was nearly neutral, and then washed with distilled water until the organic phase was neutral, and concentrated by vacuum rotary evaporation. The content of product components was analyzed by liquid chromatography with n-hexadecane as the internal standard. The mass of 3-nitrobenzoic acid was 0.72 g, the yield was 77%, and 0.11 g of unreacted benzoic acid was recovered.

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Abstract

The invention discloses a method for preparing nitrocompounds from nitrogen suboxides. Under the acceleration of molecular oxygen, nitrogen suboxides, such as nitrogen monoxide, nitrogen dioxide, nitrous oxide, nitrogen trioxide, nitrogen tetroxide and the like, reacts with alicyclic compounds, aromatic compounds and heterocyclics under the actions of heteropoly acid salts (such as aluminosilicate, phosphate aluminosilicate, sodium phosphomolybdate and the like), transition metal oxides, triphenylphosphine metal organic complexes and transition metal ion clay catalysts to obtain the nitrocompounds. The method disclosed by the invention is used for substituting the traditional industrial preparation method for preparing nitrocompounds from nitrogen pentoxide, nitric acid, nitrate, nitrate ester and other high-valence nitrogen (V) compounds; and the invention enhances the atom utilization ratio of the industrial nitrocompound preparation reaction by nitrification, and has the characteristic of atom economy in industrial preparation of nitrocompounds.

Description

Technical field [0001] The invention relates to a method for preparing nitro compounds, in particular to a method that uses low-valent nitrogen oxides (nitrogen monoxide, nitrogen dioxide, nitrous oxide, nitrous trioxide, nitrous tetroxide, etc.) to replace high-priced Nitrogen ( ) A method for preparing nitro compounds from compounds (nitrogen pentoxide, nitric acid, nitrate, nitrate ester, etc.). Background technique [0002] The easy conversion of nitro compounds and their nitro functional groups are widely used as dyes, drugs (such as medicines, pesticides), perfumes, high energy density materials, and intermediates and other chemicals. Therefore, the wide application characteristics of nitro compounds Has long been concerned by the field of fine organic synthesis. At present, the industrial preparation of nitro compounds uses pentavalent nitrogen nitric acid in a strong acid medium such as sulfuric acid or acetic acid. These preparation methods have been applied for nearly...

Claims

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Application Information

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IPC IPC(8): C07C205/45C07C201/08C07C205/22C07C205/57C07C205/12C07C205/06C07D213/61
Inventor 彭新华
Owner 彭新华
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