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A method for preparing nitro compounds using nitrogen suboxides

A technology for nitro compounds and oxides is applied in one field to achieve the effects of improving atomic economy, improving energy conservation and emission reduction, and high regioselectivity

Active Publication Date: 2011-12-14
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, add 0.84 g (10.0 mmol) cyclopentanone, 0.50 g HZSM-5 and 1.00 mL (15.7 mmol) dinitrogen tetroxide, and stir the reaction at 0.051 MPa and room temperature for 15 hours in an oxygen atmosphere. After the reaction, oxygen was introduced into the reaction mixture under normal pressure until the nitrogen oxides completely escaped from the reactor to the cold trap recovery device, 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 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 gas chromatography with nitrobenzene as internal standard. The quality of 2-nitrocyclopentanone and 3-nitrocyclopentanone is 0.91g, and the productive rate is 71%, wherein the mass fraction of 2-nitr...

Embodiment 2

[0031] In a reactor with 20 mL of dichloromethane, add 0.94 g (10.0 mmol) of phenol and 0.57 g of HZSM-5, under the conditions of magnetic stirring at 0.011MPa and a temperature of 0 ~ 5 ° C, in nitrogen monoxide and oxygen atmosphere Reacted for 9 hours. After the reaction is finished, oxygen is fed into the reaction mixture at normal pressure until the nitrogen oxides completely escape from the reactor, and then the catalyst is filtered out. The filtrate was washed with 5% (m / m) sodium bicarbonate aqueous solution until 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 gas chromatography with nitrobenzene as internal standard. The mass of nitrophenol was 1.16 g, and the yield was 83%, in which the mass fraction of 2-nitrophenol was 37%, the mass fraction of 3-nitrophenol was 10%, and the mass fraction of 4-nitrophenol was 53%.

Embodiment 3

[0033] In a reactor 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 in an air atmosphere at 0.15 MPa and room temperature for 15 hours. After the reaction was completed, oxygen was introduced into the reaction mixture under normal pressure until the nitrogen oxides completely escaped to the cold trap reaction receiver, and then the catalyst was filtered out. The filtrate was washed with 5% (m / m) sodium bicarbonate aqueous solution until 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 internal standard. The quality 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 a nitro compound from a low-valent nitric oxide. The method comprises that a low-valent nitric oxide such as nitric oxide, nitrogen dioxide, nitrous oxide, nitrogen trioxide, dinitrogen tetroxide and the like react with an alicyclic compound, an aromatic compound or a heterocyclic compound through promoting effects of molecular oxygen and effects of catalysts comprising a transition metal oxide, a triphenylphosphine metal organic complex, transition metal ion clay and heteropoly acid salts such as aluminosilicate, silicoaluminophosphate, sodium phosphomolybdate and the like. The method can replace the traditional industrial method for preparing a nitro compound from a high-valent (V-valent) nitrogen compound such as nitrogen pentoxide, hydrogen nitrate, nitric acid salts, nitric acid esters and the like. The method improves an atom utilization rate of a reaction in industrial nitration preparation of a nitro compound, and has atom economic characteristics of industrial preparation of a nitro compound.

Description

technical field [0001] The present invention relates to a method for preparing nitro compounds, especially a method for replacing high-valent nitrogen oxides (nitrogen monoxide, nitrogen dioxide, dinitrogen monoxide, dinitrogen trioxide, dinitrogen tetroxide, etc.) Nitrogen ( ) compounds (nitrogen pentoxide, nitric acid, nitrates, nitrates, etc.) to prepare nitro compounds. Background technique [0002] The easy conversion of nitro compounds and their nitro functional groups is widely used as chemicals such as dyes, drugs (such as medicines, pesticides), spices, high energy density materials, and their intermediates. Therefore, the wide application characteristics of nitro compounds It has long been concerned by the field of fine organic synthesis. At present, the industrial preparation of nitro compounds uses nitric acid of pentavalent nitrogen under the conditions of strong acid medium such as sulfuric acid or acetic acid. These preparation methods have been used for ne...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/08C07C205/45C07C205/22C07C205/57C07C205/12C07C205/06C07D213/61
Inventor 彭新华
Owner 彭新华
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