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Method for preparing acifluorfen by catalyzing and nitrifying with solid super acid

A technology of solid super acid and acifluorfen, which is applied in the field of catalytic nitration of 3-[2-chloro-4-phenoxy]benzoic acid to prepare acifluorfen, which can solve the difficulties of waste acid recovery and reuse, A large amount of acid-containing wastewater, corrosion equipment and other problems, to achieve the effect of reusable environmental pollution, high catalytic activity, easy to separate

Inactive Publication Date: 2011-06-15
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid is produced by nitration technology widely used in industry (WO9710199). There are two main problems in this process: One is that there is no nitrification selectivity, and the production cost of the reaction mixture and isomer separation is very high; the other is that it is difficult to recycle the waste acid after the reaction, and a large amount of acid-containing wastewater is produced during post-treatment, which not only corrodes the equipment, but also causes serious environmental damage. Pollution
Wang Tao et al. used montmorillonite, molecular sieve, silica, and alumina as carriers to synthesize a loaded superacid for the green nitration of diphenyl ether derivatives, showing good catalytic activity with a yield of 74.3%. , the product content is 81.1% (CN101165043), but this invention still fails to solve the problem of low selectivity of acifluorfen prepared by nitration
The present invention extensively screens various superacids on the basis of predecessors' research, and finds that solid superacids with ferric oxide, zirconium dioxide and titanium dioxide as carriers can catalyze 3-[2-chloro-4-(trifluoro Methyl) phenoxy] benzoic acid nitration to prepare acifluorfen has higher selectivity, the selectivity can be increased to 92%, and the yield is 88%. The relevant research has not been reported in the literature, and has a good Industrialization prospect

Method used

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  • Method for preparing acifluorfen by catalyzing and nitrifying with solid super acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Example 1: SO 4 2- / ZrO 2 Preparation of Solid Superacid Catalyst

[0015] Take 40g of zirconium oxychloride solid, and configure it into a 10% zirconium oxychloride aqueous solution with deionized water. While stirring at room temperature, concentrated ammonia water was slowly added dropwise therein to adjust the pH to 9-10, a large amount of precipitates were precipitated, and the formed precipitates were aged at room temperature for 20 h. After aging, filter and wash the filter cake to be free of Cl - (Detected with 0.1mol / L silver nitrate solution) until detected. The filter cake was dried at 110°C for 14h, impregnated with 0.25mol / L sulfuric acid at a ratio of 5mL / g for 1h, dried at 110°C overnight after filtration, ground to 100 mesh, roasted at 550°C for 3h, taken out and placed in Cool in a desiccator to obtain 14g SO 4 2- / ZrO 2 .

Embodiment 2

[0016] Example 2: SO 4 2- / TiO 2 Preparation of Solid Superacid Catalyst

[0017] Take 30g TiCl 4 Add slowly to 0.2 mol / L hydrogen chloride deionized aqueous solution at 0°C to form a 20% solution. Slowly add concentrated ammonia water dropwise under stirring at room temperature to adjust the pH to 9-10, a large amount of precipitates are precipitated, and the formed precipitates are aged at room temperature for 20 h. After aging, filter and wash the filter cake to be free of Cl - Until it is detected (detected with 0.1mol / L silver nitrate solution), the filter cake is dried at 110°C for 14h, impregnated with 0.25mol / L sulfuric acid at a ratio of 10mL / g for 1h, filtered and baked at 110°C Dry overnight, grind to 200 mesh, bake at 500°C for 3 hours, take it out and put it in a desiccator to cool, and obtain 11.7g SO 4 2- / TiO 2 .

Embodiment 3

[0018] Example 3: SO 4 2- / Fe 2 o 3 Preparation of Solid Superacid Catalyst

[0019] Take 100g of ferric nitrate hydrate, and use deionized water to configure a 10% ferric nitrate aqueous solution. Slowly add concentrated ammonia water dropwise under stirring at room temperature to adjust the pH to 9-10, a large amount of precipitates are precipitated, and the formed precipitates are aged at room temperature for 20 h. After aging, filter and wash the filter cake to be free of Cl - Until it is detected (detected with 0.1mol / L silver nitrate solution), the filter cake is dried at 110°C for 14h, impregnated with 0.25mol / L sulfuric acid at a ratio of 15mL / g for 2h, filtered and baked at 110°C Dry overnight, grind to 300 mesh, bake at 500°C for 3 hours, take it out and put it in a desiccator to cool, and get 20g SO 4 2- / Fe 2 o 3 .

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Abstract

The invention discloses a method for preparing acifluorfen by catalyzing and nitrifying with solid super acid and relates to a preparation method of a nitro compound. The method comprises the following steps of: reacting 3-[2-chlorine-4-(trifluoromethyl) phenoxyl] benzoic acid and fuming nitric acid under the catalysis of solid super acid for 1-20 hours at 20-80 DEG C in the presence of acetic anhydride in dichloroethane; filtering and recovering a solid super acid catalyst; and layering, drying and evaporating the solution to obtain an acifluorfen product. In the invention, the used solid super acid is a load type super acid using metallic oxides as carriers, wherein the carriers comprise iron sesquioxide, titanium dioxide and zirconium dioxide. Compared with the traditional mixed acid nitrification, the method has the advantages of high yield, good selectivity, easiness of product separation, catalyst recycling capability and low environmental pollution and has industrial application prospect.

Description

technical field [0001] The present invention relates to a preparation method of nitro compounds, in particular to a preparation method of trifluorocarboxylate by catalytic nitration of 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid using solid superacid as catalyst The fenugreek method. technical background [0002] Acifluorfen is a kind of widely used high-efficiency herbicide, and it is also an intermediate in the synthesis of other pesticides. At present, 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid is produced by nitration technology widely used in industry (WO9710199). There are two main problems in this process: One is that there is no nitrification selectivity, and the production cost of the reaction mixture and isomer separation is very high; the other is that it is difficult to recycle the waste acid after the reaction, and a large amount of acid-containing wastewater is produced during post-treatment, which not only corrodes the equipment, but also cau...

Claims

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Application Information

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IPC IPC(8): C07C205/59C07C201/08B01J27/053
CPCY02P20/584
Inventor 朱红军施路章勤吴涛王凯肖琪王昆彦陈琛席彬斌
Owner NANJING UNIV OF TECH
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