Process for preparing P-nitro benzoic acid by bionically catalystically oxidizing P-nitro toluene with oxygen

A technology of p-nitrobenzoic acid and p-nitrotoluene, applied in chemical instruments and methods, preparation of organic compounds, physical/chemical process catalysts, etc., can solve problems such as health threats to industrial operators, and achieve the goal of reducing production costs Effect

Inactive Publication Date: 2007-04-11
BEIJING UNIV OF TECH
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Problems solved by technology

But its weak point is that both the preparation of p-nitrobenzoic acid and the preparation of intermediate product p-nitrobenzaldehyde all adopt anhydrous methanol as solvent, and anhydrous methanol not only has potential explosion under pure oxygen conditions (reaction or distillation) Hazardous, but also a potential threat to the health of laboratory or industrial operators

Method used

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  • Process for preparing P-nitro benzoic acid by bionically catalystically oxidizing P-nitro toluene with oxygen
  • Process for preparing P-nitro benzoic acid by bionically catalystically oxidizing P-nitro toluene with oxygen
  • Process for preparing P-nitro benzoic acid by bionically catalystically oxidizing P-nitro toluene with oxygen

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Effect test

Embodiment 1

[0022] Get 2mg cobalt phthalocyanine (i.e. R=H in general formula (I), M 1 =Co), 1.4g p-nitrotoluene and 2g sodium hydroxide were packed into a 200mL autoclave, and 38mL of ethanol aqueous solution (95% ethanol: 22mL, water: 16mL) was added containing 55% (V / V) of ethanol, and the Oxygen gas with a pressure of 2.0 MPa was introduced, and the reaction was carried out in a water bath at a temperature of 40° C. for 14 hours. After the reaction, samples were taken, and the reaction mixture was filtered with suction to remove the catalyst, then 15 mL of distilled water was added, neutralized with dilute hydrochloric acid, and filtered. The obtained product was analyzed and detected by high-pressure liquid chromatography, and the yield of p-nitrobenzoic acid was 96.2%.

Embodiment 2

[0024] Get 22mg iron phthalocyanine (i.e. R=H in general formula (I), M 1 =Fe), 6.3g p-nitrotoluene and 9.0g sodium hydroxide were put into a 200mL autoclave, and 38mL of ethanol aqueous solution (95% ethanol: 28mL, water: 10mL) containing 70% (V / V) ethanol was added, The reaction pressure was 3.0 MPa, the temperature was controlled at 35° C. in a water bath, and the reaction was carried out for 8 hours. The aftertreatment steps are the same as in Example 1, and the obtained product is analyzed and detected by high-pressure liquid chromatography, and the yield of p-nitrobenzoic acid is 96.4%.

Embodiment 3

[0026] Get 10mg copper phthalocyanine (i.e. R=H in general formula (I), M 1 =Cu), 1.0g of p-nitrotoluene and 2.5g of sodium hydroxide were charged into a 200mL autoclave, and 38mL of aqueous ethanol (95% ethanol: 30mL, water: 8mL) containing 75% (V / V) of ethanol was added, The oxygen pressure is 2.5MPa, the temperature is controlled at 40°C in a water bath, and the reaction is performed for 10 hours. The aftertreatment steps are the same as in Example 1, and the obtained product is analyzed and detected by high-pressure liquid chromatography, and the yield of p-nitrobenzoic acid is 93.2%.

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Abstract

The present invention is bionically catalyzed p-nitro toluene oxidizing process for preparing p-nitro benzoic acid. In the process, p-nitro toluene material is oxidized with introduced O2 of 0.8-3.0 MPa pressure inside water solution of alcohol at 35-55 deg.c in the presence of metal phthalocyanine, monocuclear metalloporphyrin or mu-oxybinuclear metalloporphyrin catalyst in the amount of 0.01-1.0 wt% of p-nitro toluene for 2-14 hr to obtain p-nitro benzoic acid. The process of the present invention is simple and has low toxicity, high operation safety, high product yield and low cost.

Description

technical field [0001] The invention relates to a preparation method of aromatic acid, in particular to a method for preparing p-nitrobenzoic acid by biomimetic catalyzing oxygen oxidation of p-nitrotoluene. Background technique [0002] p-Nitrobenzoic acid is an important intermediate for the preparation of medicines, dyes, veterinary drugs, photosensitive materials, pesticides and high-strength fibers and resins. The method for synthesizing p-nitrobenzoic acid reported in the literature at present mainly adopts the catalytic oxygen oxidation method in alkaline medium. She Yuanbin and others have reported that metal phthalocyanines (Org. Process Res. Dev. 2005, 9: 297-301) or metal porphyrins (Org. Process Res. Dev. 2006 , 10 (4), 757-761) is the method for synthesizing p-nitrobenzoic acid by catalyzing the oxidation of p-nitrotoluene with biomimetic catalyst, this method solves the equipment corrosion and environmental pollution existing in the synthesis of p-nitrobenzoic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C205/57C07C201/12B01J31/22B01J31/28
Inventor 佘远斌段立丽曾小静王兰芝钟儒刚
Owner BEIJING UNIV OF TECH
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