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Phase transfer catalyst for haloarene replacing fluorination

A phase transfer catalyst, halogenated aromatic hydrocarbon technology, applied in the direction of physical/chemical process catalyst, organic compound/hydride/coordination complex catalyst, organic halogenation, etc. High temperature resistance, poor product quality and other problems, to achieve the effect of reducing temperature, easy post-processing, high product quality and purity

Inactive Publication Date: 2003-11-26
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When preparing fluorinated aromatic hydrocarbons, due to the immiscibility between aromatic hydrocarbons and metal fluorides, phase transfer catalysts are often used, such as quaternary ammonium salts, crown ethers or polyethers, but must be carried out at high temperatures, and the reaction temperature is above 230 ° C. As a result, it is necessary to Large excess of metal fluoride, and need to use aprotic polar solvent, quaternary ammonium salt as phase transfer catalyst, and quaternary ammonium salt is not resistant to high temperature, easy to decompose, and a large number of by-products are generated, post-processing is troublesome, and the product quality is poor
The effect of polyether as a phase transfer catalyst is poor, and the recovery of crown ether as a catalyst is difficult

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 2

[0017] Preparation of 4-fluoronitrobenzene

[0018] Mix 7.5g of anhydrous potassium fluoride powder, 60mL of xylene, 15.8g of p-nitrochlorobenzene, and 1g of p-hydrocalix[6]arene catalyst into the reactor, heat up to 140°C, and react at this temperature After 6 hours, cool down to below 100°C, add 100mL of toluene, and filter with suction to remove potassium fluoride and inorganic salts. After removing the solvent, the filtrate was distilled in vacuum to obtain 13.28 g of 4-fluoronitrobenzene with a yield of 93.87%. Product melting point: 26℃~27℃, boiling point: 204℃~205℃. The purity of the product analyzed by gas chromatography was 97.21%. Comparative example 2

example 3

[0021] Preparation of 3,4,5-trifluorobenzoic acid

[0022] Put 10g of anhydrous potassium fluoride powder, 100mL of sulfolane, 14.5g of 3,4,5-trichlorobenzoyl chloride, and 1g of p-tert-butylcalix[4]arene methyl ether catalyst into the reactor after thorough mixing, and heat up to 220°C, react at this temperature for 2h, then lower the temperature to below 20°C, add 100mL of anhydrous methanol, and react at 60°C for 6h. The esterified product was suction filtered to remove potassium fluoride and inorganic salts. After removing the solvent, the filtrate was added to about 50 mL of water, and precipitates were precipitated, filtered with suction, washed with water, and dried to obtain 16.22 g of the product, with a yield of 92.10%. The melting point of the product: 97°C to 99°C, and the purity of the product by liquid chromatography analysis is 98.00%. Comparative example 3

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Abstract

The present invention belongs to fluorination catalyst technology. The catalyst is applied in the haloarene replacing fluorination between the haloarene and fluorinating agent inside sulfolane solution. The present invention features the catalyst being calixarene or its derivative, consumption of 0.01-1 mol and using temperature 80-230 deg.c. Using the catalyst in haloarene replacing fluorination can simplify the technological process, lower the product cost, raise the product yield and purity and simplify post-treatment. The present invention is suitable for industrial production.

Description

technical field [0001] The invention relates to a phase transfer catalyst used in the displacement fluorination reaction of halogenated aromatic hydrocarbons. It belongs to the fluorination reaction catalyst technology. Background technique [0002] Aromatic fluorine-containing organic compounds are widely used, involving medicine, pesticides, dyes and many other fields. These compounds are used to synthesize herbicides, fungicides, antineoplastic drugs, antipsychotics, anti-senile dementia drugs, functional dyes and other products Has a unique effect. When preparing fluorinated aromatic hydrocarbons, due to the immiscibility between aromatic hydrocarbons and metal fluorides, phase transfer catalysts are often used, such as quaternary ammonium salts, crown ethers or polyethers, but must be carried out at high temperatures, and the reaction temperature is above 230 ° C. As a result, it is necessary to Large excess metal fluorides, and need to us...

Claims

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Application Information

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IPC IPC(8): B01J31/02C07B39/00
Inventor 冯亚青孟舒献姚光源
Owner TIANJIN UNIV
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