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Method for green catalytic synthesis of nitrobenzaldehyde

A technology of nitrobenzaldehyde and nitrotoluene, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry and other directions, can solve problems such as hydrogen bromide pollution, and achieves reduction of catalytic cost, low reaction conditions, Inexpensive effect

Active Publication Date: 2016-04-20
NANJING UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The yield is 51.8%, but the reaction is dangerous, and the hydrogen bromide pollution is serious

Method used

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  • Method for green catalytic synthesis of nitrobenzaldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 1) Add o-nitrotoluene (0.1mol, 13.7g), N,N-dimethylformamide diacetal (0.2mol, 26ml) and N,N-dimethylformamide (75ml) into the reactor , heated to reflux, and reacted for 19h.

[0024] 2) After the reaction is completed, cool down to room temperature to obtain a deep red N,N-dimethyl-o-nitrostyrylamine solution, and recover N,N-dimethylformamide diacetal by atmospheric distillation, and then recover N by distillation under reduced pressure. , N-dimethylformamide, the residual temperature was lowered to room temperature, slowly added 150ml of water, stirred and filtered with suction to obtain N,N-dimethyl-o-nitrostyrylamine, which was directly used in the next step.

[0025] 3) Dissolve N,N'-disalicylaldehyde ethylenediamine manganese (0.005mol) and N,N-dimethyl-o-nitrostyrylamine prepared in the previous step in 250ml of acetonitrile, cool in ice water, slowly drop Add 60ml of 30%wt hydrogen peroxide (0.6mol), drop it within 30min, remove the ice bath, and react at roo...

Embodiment 2

[0028] The process was the same as in Example 1, except that the o-nitrotoluene in the first step was changed to p-nitrotoluene, the toluene in the fourth step was changed to n-hexane, and other factors remained unchanged to obtain 11.0 g of yellow crystals. Melting point: 105.6-106.8°C, yield 74.2% (calculated as p-nitrobenzaldehyde), purity (HPLC): 98.2%.

Embodiment 3

[0030] The process was the same as in Example 1, except that the o-nitrotoluene in the first step was changed to m-nitrotoluene, and the toluene in the fourth step was changed to cyclohexane, and other factors remained unchanged to obtain 6.28 g of yellow crystals. Melting point: 58-59.2°C, yield 43.1% (calculated as p-nitrobenzaldehyde), purity (HPLC): 96.5%.

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Abstract

The invention discloses a method for green-catalytically synthesizing nitrobenzaldehyde. With nitrotoluene as a raw material, the nitrotoluene is firstly reacted with DMF and DMFA to generate N,N-dimethylnitrostyrylamine, and then the N,N-dimethylnitrostyrylamine is oxidized to generate the nitrobenzaldehyde with hydrogen peroxide as a green oxidizing agent and a metal Schiff base as a catalyst. The method is green, environmental-protective, low in cost, mild in reaction conditions and increased in yield when being compared with a method in the prior art.

Description

technical field [0001] The invention belongs to the field of organic synthesis and relates to the synthesis of nitrobenzaldehyde, in particular to a method for synthesizing nitrobenzaldehyde by using metal Schiff base as a catalyst and using hydrogen peroxide as an oxidant in a two-step green catalytic method. Background technique [0002] Nitrobenzaldehyde includes o-nitrobenzaldehyde, m-nitrobenzaldehyde, and p-nitrobenzaldehyde, all of which are important chemical intermediates and are widely used in the synthesis of pharmaceuticals and dye intermediates. Nitrobenzaldehyde has great demand in domestic and foreign markets, so the research on nitrobenzaldehyde has important practical and theoretical significance. [0003] The traditional bromination-hydrolysis-oxidation production method for the domestic synthesis of o-nitrobenzaldehyde has the disadvantages of harsh reaction conditions, high toxicity, high requirements for equipment, and environmental pollution; the synthe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C205/44C07C201/12
Inventor 李斌栋虞超
Owner NANJING UNIV OF SCI & TECH
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