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The preparation method of pentafluorobenzaldehyde

A technology of pentafluorobenzaldehyde and pentafluorobenzonitrile, which is applied in the field of preparation of pentafluorobenzaldehyde, can solve the problems of high consumption of Ni-Al alloy, high equipment requirements, and difficult disposal of waste salt, etc., so as to reduce the generation of waste, Effect of reducing environmental pollution and reducing reaction steps

Active Publication Date: 2019-05-21
DALIAN QIKAI MEDICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method requires hydrogenation in an autoclave, which leads to low production capacity of the scale-up production of the factory, and the acid used is easy to corrode the kettle body, which requires relatively high equipment requirements
[0005] Document Journal of Chemical Society C P1343-1348 1971, see page 1348. This document shows that pentafluorobenzaldehyde can be prepared from pentafluorobenzonitrile. The problem is that the consumption of Ni-Al alloy is too large, and it needs to be treated with sodium hydroxide to form Raney Nickel, the yield is relatively low
[0006] Most of the remaining documents use pentafluorobenzoic acid derivatives for reduction to produce pentafluorobenzaldehyde, and pentafluorobenzoic acid derivatives are usually prepared by hydrolysis of pentafluorobenzonitrile with sulfuric acid, which will produce a large amount of waste acid, and waste salt is difficult to obtain. deal with

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add 4.9Kg of pentafluorobenzonitrile, 15Kg of formic acid, and 8.5Kg of water to the 50L reactor equipped with condenser, mechanical stirring, and thermometer sleeve. Eight batches were put into the reaction kettle, exothermic during the process, and maintained in a reflux state. After adding the nickel-aluminum alloy powder, reflux for 1 hour, take a sample, detect pentafluorobenzonitrile <0.2% in gas phase, cool down to room temperature, filter, add 25Kg of water and 10Kg of dichloromethane to the filtrate for extraction, and add 10Kg of dichloromethane to the separated water layer. Methylene chloride was extracted once, after the organic layers obtained from the two extractions were combined, 5% aqueous sodium bicarbonate solution was added, the pH was adjusted to 6-7, the oil layer was separated, the dichloromethane was recovered by atmospheric distillation, and the distilled mother liquor was rectified, At the pressure of -0.09Mpa and the top temperature of 108°C, ...

Embodiment 2

[0028] To be equipped with condenser, mechanical stirring, add pentafluorobenzonitrile 100g, formic acid 300g, water 170g in the 1L reaction kettle of thermometer sleeve, feed into nitrogen protection, be warming up to 70 ℃, put into 4 batches of nickel-aluminum alloy powder 45g In the reaction kettle, heat was released during the process, and it was maintained in a reflux state. After adding the nickel-aluminum alloy powder, reflux for 2 hours, take a sample, detect pentafluorobenzonitrile <0.2% by gas phase, cool down to room temperature, filter, add 450g of water and 150g of dichloromethane to the filtrate to extract once, and then add 150g of dichloromethane to the separated water layer. Methylene chloride was extracted once, after the organic layers obtained from the two extractions were combined, 5% aqueous sodium bicarbonate solution was added, the pH was adjusted to 6-7, the oil layer was separated, the dichloromethane was recovered by atmospheric distillation, and the ...

Embodiment 3

[0030] Add 90g of pentafluorobenzonitrile, 270g of formic acid, 150g of water to the 1L reactor equipped with condenser, mechanical stirring, thermometer sleeve, feed into nitrogen protection, be warming up to 90 ℃, put into 4 batches of nickel-aluminum alloy powder 40g In the reaction kettle, heat was released during the process, and it was maintained in a reflux state. After the nickel-aluminum alloy powder was added, reflux for 2 hours, take a sample, detect pentafluorobenzonitrile <0.2% by gas phase, cool down to room temperature, filter, add 400g of water and 130g of dichloromethane to the filtrate to extract once, and then add 130g of dichloromethane to the separated water layer. Methylene chloride was extracted once, after the organic layers obtained from the two extractions were combined, 5% aqueous sodium bicarbonate solution was added, the pH was adjusted to 6-7, the oil layer was separated, the dichloromethane was recovered by atmospheric distillation, and the distil...

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Abstract

The invention relates to a preparation method of pentafluorobenzaldehyde, and belongs to the field of fine chemical product preparation. According to the preparation method, catalyst Ni-Al alloy, pentafluorobenzonitrile, and formic acid are subjected to reaction in water to prepare pentafluorobenzaldehyde. Ni-Al alloy is adopted, formic acid and water are taken as reducing agents, and pentafluorobenzaldehyde is prepared via reduction of pentafluorobenzonitrile. The preparation method is capable of realizing direction reduction of pentafluorobenzonitrile into pentafluorobenzaldehyde, so that reaction steps are reduced, generation of waste is reduced, production cost is reduced, and environmental pollution is reduced.

Description

technical field [0001] The invention relates to a preparation method of pentafluorobenzaldehyde, and belongs to the field of preparation of fine chemical products. Background technique [0002] Pentafluorobenzaldehyde is an important pesticide and pharmaceutical intermediate, and there are the following reports on the disclosed technology at home and abroad. [0003] The document "Highly fluorinated Analogues of Pharmacologically Active Compounds" N.B.Chapman, J.Chem.Soc., 1967, introduced the method for preparing pentafluorobenzaldehyde from pentafluorobenzonitrile and anhydrous stannous chloride, due to the need to use ether and hydrogen chloride Gas, it is not easy to expand production. [0004] Patent US20040110990 domestically proposes a method for catalytic reduction of substituted benzonitrile to substituted benzaldehyde in the presence of water, acid, catalyst containing nickel and aluminum, and hydrogen for CN03127891. This method requires autoclave hydrogenation,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/44C07C47/55
CPCC07C45/44C07C47/55
Inventor 孙发明姜殿平张洪学赵玉国
Owner DALIAN QIKAI MEDICAL TECH
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