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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 alloys, high equipment requirements, and low production capacity, so as to reduce the generation of waste and reduce the environment Pollution, the effect of reducing production costs

Active Publication Date: 2017-02-15
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 into a 50L reaction kettle equipped with a condenser, mechanical stirring, and a thermowell, pass through nitrogen protection, heat up to 65°C, and divide 2.2Kg of nickel-aluminum alloy powder into 8 batches were put into the reactor, exothermic during the process, maintained in a reflux state. Reflux for 1 hour after adding the nickel-aluminum alloy powder, take a sample, detect that pentafluorobenzonitrile is <0.2% by gas phase, cool down to room temperature, filter, add 25Kg water and 10Kg dichloromethane to the filtrate for extraction, add 10Kg dichloromethane to the separated water layer Extract once with methyl chloride, combine the organic layers obtained from the two extractions, add 5% sodium bicarbonate aqueous solution, adjust the pH to 6-7, separate the oil layer, and recover dichloromethane by atmospheric distillation, and rectify the mother liquor after distillation. At a pressur...

Embodiment 2

[0028] Add 100g of pentafluorobenzonitrile, 300g of formic acid, and 170g of water into a 1L reaction kettle equipped with a condenser, mechanical stirring, and a thermowell, pass through nitrogen protection, raise the temperature to 70°C, and add 45g of nickel-aluminum alloy powder in 4 batches In the reaction kettle, heat is released during the process and maintained in a reflux state. Reflux for 2 hours after the nickel-aluminum alloy powder is added, take a sample, detect that pentafluorobenzonitrile is <0.2% by gas phase, cool down to room temperature, filter, add 450g water and 150g dichloromethane to the filtrate to extract once, add 150g dichloromethane to the separated water layer Extract once with methyl chloride, combine the organic layers obtained from the two extractions, add 5% sodium bicarbonate aqueous solution, adjust the pH to 6-7, separate the oil layer, and recover dichloromethane by atmospheric distillation, and rectify the mother liquor after distillation....

Embodiment 3

[0030] Add 90g of pentafluorobenzonitrile, 270g of formic acid, and 150g of water into a 1L reaction kettle equipped with a condenser, mechanical stirring, and a thermometer sleeve, pass through nitrogen protection, raise the temperature to 90°C, and add 40g of nickel-aluminum alloy powder in 4 batches In the reaction kettle, heat is released during the process and maintained in a reflux state. Reflux for 2 hours after adding the nickel-aluminum alloy powder, take a sample, detect that pentafluorobenzonitrile is <0.2% by gas phase, cool down to room temperature, filter, add 400g water and 130g dichloromethane to the filtrate to extract once, and then add 130g dichloromethane to the separated water layer Extract once with methyl chloride, combine the organic layers obtained from the two extractions, add 5% sodium bicarbonate aqueous solution, adjust the pH to 6-7, separate the oil layer, and recover dichloromethane by atmospheric distillation, and rectify the mother liquor after...

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PUM

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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, which belongs to the field of preparation of fine chemical products. Background technique [0002] Pentafluorobenzaldehyde is an important pesticide and pharmaceutical intermediate. There are several reports on domestic and foreign public technology. [0003] The document "Highly fluorinated Analogues of Pharmacologically Active Compounds" N.B.Chapman, J.Chem.Soc., 1967, introduced the method for preparing pentafluorobenzaldehyde by pentafluorobenzonitrile and anhydrous tin protochloride, due to the need to use ether and hydrogen chloride Gas, difficult to expand production. [0004] Patent US20040110990 domestically proposes a method for catalytically reducing substituted benzonitriles to substituted benzaldehydes in the presence of water, acid, a catalyst containing nickel and aluminum and hydrogen for CN03127891. This method requires hydrogenation in an autoclave, which lead...

Claims

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Application Information

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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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