Chemical synthesis method of 2,3,4,5-phenyl tetrafluoride formyl chloride

A tetrafluorobenzoyl chloride, chemical synthesis technology, applied in 2 fields, can solve problems affecting product appearance and quality, high production cost, difficult handling, etc., achieve great implementation value and social and economic benefits, safe and reliable production, and process routes advanced effects

Active Publication Date: 2009-02-25
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The tail gas of the above-mentioned process contains a large amount of asphyxiating sulfur dioxide (one of the six indicators strictly controlled by the national environmental protection on the atmosphere), which is difficult to deal with. At present, the mixture of sodium sulfite and sodium chloride is mainly prepared by alkali absorption, but there are big problems in market sales. Moreover, because it is an aqueous solution after being absorbed by alkali, it must be concentrated to obtain a mixture of sodium sulfite and sodium chloride. The production process consumes a lot of energy and the production cost is relatively high.
At the same time, due to the concentrated release of sulfur dioxide duri

Method used

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  • Chemical synthesis method of 2,3,4,5-phenyl tetrafluoride formyl chloride

Examples

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Example Embodiment

Example 1

The amount ratio of the feed material is 2,3,4,5-tetrafluorobenzoic acid: bis(trichloromethyl) carbonate: the catalyst is 1:0.34:0.01, and the catalyst is 1-N-piperidinyl supported by Merrifield resin. 4-formaldehyde, the organic solvent is chloroform, and the amount is twice the mass of 2,3,4,5-tetrafluorobenzoic acid.

Into a 250mL three-necked flask equipped with a thermometer, reflux condenser and mechanical stirring, add 19.4g (100mmol) of 2,3,4,5-tetrafluorobenzoic acid and 17.8g (60mmol) of bis(trichloromethyl) carbonate , 39ml of 2-methyltetrahydrofuran and 0.15g (2mmol) of N,N-dimethylformamide. After the addition, the temperature is increased to 60-65℃, and the reaction is kept for 4h. After the reaction is completed, the solvent is evaporated under normal pressure, and the vacuum is distilled again. The vacuum degree is 6.3kpa. The 85-86℃ fraction is collected by distillation to obtain 19.6g. Product yield 92.1%, 98.6% purity (GC).

Example Embodiment

Example 2

The ratio of the amount of the feed material to 2,3,4,5-tetrafluorobenzoic acid: bis(trichloromethyl) carbonate: the catalyst is 1:0.5:0.01, and the feed amount of 2,3,4,5-tetrafluorobenzoic acid The amount of bis(trichloromethyl) carbonate is 19.4g (100mmol), the dosage of bis(trichloromethyl)carbonate is 14.9g (50mmol), the catalyst is 1-N-piperidinyl-4-carbaldehyde supported by the repeated Merrifield resin, and the amount is 0.94 g (1 mmol), the organic solvent is chloroform, and the amount is twice the mass of 2,3,4,5-tetrafluorobenzoic acid.

The reaction temperature is the reflux temperature, and other operations are the same as in Example 1, to obtain 18.5 g of 2,3,4,5-tetrafluorobenzoyl chloride, with a product yield of 87.1% and a purity of 99.6% (GC).

Example Embodiment

Example 3

The quantity ratio of the feed material is 2,3,4,5-tetrafluorobenzoic acid: bis(trichloromethyl) carbonate: catalyst is 1:0.6:0.02, catalyst is N,N-dimethylformamide, organic solvent It is 2-methyltetrahydrofuran, and its dosage is twice the mass of 2,3,4,5-tetrafluorobenzoic acid.

Into a 250mL three-necked flask equipped with a thermometer, reflux condenser and mechanical stirring, add 19.4g (100mmol) of 2,3,4,5-tetrafluorobenzoic acid and 17.8g (60mmol) of bis(trichloromethyl) carbonate , 39ml of 2-methyltetrahydrofuran and 0.15g (2mmol) of N,N-dimethylformamide. After the addition, the temperature is increased to 60-65℃, and the reaction is kept for 4h. After the reaction is completed, the solvent is evaporated under normal pressure, and the vacuum is distilled again. The vacuum degree is 6.3kpa. The 85-86℃ fraction is collected by distillation to obtain 19.6g. Product yield 92.1%, 98.6% purity (GC).

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Abstract

The invention discloses a method for chemical synthesis of 2, 3, 4, 5-tetrafluorobenzoyl chloride. The method comprises the following steps: 2, 3, 4, 5-tetrafluorobenzoic acid reacts with bis(trichloromethyl) carbonate in an organic solvent under the action of an organic amine catalyst at the temperature of 20-100 DEG C for 1-10h, and the 2, 3, 4, 5-tetrafluorobenzoyl chloride is obtained after post treatment; and the organic amine catalyst is tertiary amine containing N-formoxyl group or solid-phase supported tertiary amine containing the N-formoxyl group. The method has the advantages of mild reaction conditions, high reaction yield and less three wastes, and has greater implementation values, social benefits and economic benefits.

Description

(1) Technical field The invention relates to a chemical synthesis method of 2,3,4,5-tetrafluorobenzoyl chloride. (2) Background technology 2,3,4,5-Tetrafluorobenzoyl chloride is an important intermediate used in the synthesis of chemical raw materials, such as the production of ofloxacin or levofloxacin with it. Before the present invention provides, the chemical synthesis method of 2,3,4,5-tetrafluorobenzoyl chloride in the prior art mostly is chlorinated with 2,3,4,5-tetrafluorobenzoic acid and thionyl chloride prepared. As proposed in US4777253, 14.5g of 2,3,4,5-tetrafluorobenzoic acid and 152ml of thionyl chloride were refluxed for 4 hours under the catalysis of a small amount of DMF. The tail gas of the above-mentioned process contains a large amount of asphyxiating sulfur dioxide (one of the six indicators strictly controlled by the national environmental protection on the atmosphere), which is difficult to deal with. At present, the mixture of sodium sulfite and so...

Claims

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Application Information

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IPC IPC(8): C07C63/10C07C51/60
Inventor 苏为科陈志卫杨郭明姜灵陈寅镐王超
Owner ZHEJIANG UNIV OF TECH
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