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Catalytic reduction method of benzonitrile to benzoaldehyde

A technology of catalysts and compounds, applied in the fields of nitrile reduction and hydrolysis preparation, organic chemistry, etc.

Inactive Publication Date: 2004-03-24
BAYER AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this approach is limited to specific substitution patterns, in particular to the presence of the strongly electron-withdrawing trifluoromethyl group at the para position

Method used

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  • Catalytic reduction method of benzonitrile to benzoaldehyde
  • Catalytic reduction method of benzonitrile to benzoaldehyde
  • Catalytic reduction method of benzonitrile to benzoaldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] 10.8 g of 3,5-bis(trifluoromethyl)-benzonitrile in 70 g of 80% formic acid and 0.9 g of Ni-Al-50 / 50 alloy were initially placed in the autoclave. The autoclave was pressurized with 15 bar nitrogen and heated to 70°C. Once the reaction temperature was reached, the hydrogen pressure was increased to 3 bar and kept constant for 10 hours. Subsequently, the mixture was cooled and filtered, and the solution was extracted with toluene, followed by fractional distillation under reduced pressure, yielding 8.8 g of 3,5-bis(trifluoromethyl)-benzaldehyde (80% of theory).

Embodiment 2

[0064] 7.7 grams of 3-trifluoromethylbenzonitrile in 70 grams of 70% formic acid and 0.9 grams of Ni-Al-50 / 50 alloy were first placed in the autoclave. The autoclave was pressurized with 15 bar nitrogen and heated to 80°C. Once the reaction temperature was reached, the hydrogen pressure was increased to 10 bar and kept constant for 7 hours. Subsequently, the mixture was cooled and filtered, and the solution was extracted with toluene, followed by fractional distillation under reduced pressure, yielding 6.5 g of 3-trifluoromethylbenzaldehyde (85% of theory).

Embodiment 3

[0066] 7.7 grams of 3-trifluoromethylbenzonitrile in 50 grams of 75% formic acid and 1 gram of NiFeCrAl prealloy were first placed in the autoclave. The autoclave was pressurized with 15 bar nitrogen and heated to 80°C. Once the reaction temperature was reached, the hydrogen pressure was increased to 6 bar and kept constant for 10 hours. Subsequently, the mixture was cooled and filtered, and the solution was extracted with toluene, followed by fractional distillation under reduced pressure, yielding 7.0 g of 3-trifluoromethylbenzaldehyde (89% of theory).

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Abstract

The invention relates to a process for catalytically reducing substituted benzonitriles to substituted benzaldehydes in the presence of aqueous formic acid, of a nickel- and aluminium-containing catalyst and hydrogen.

Description

technical field [0001] The present invention relates to a method for catalytically reducing substituted benzonitriles to substituted benzaldehydes in the presence of water, acid, a catalyst containing nickel and aluminum, and hydrogen. [0002] Substituted benzaldehydes are of high industrial importance as fine chemicals and active ingredient intermediates. [0003] Substituted benzaldehydes are often prepared by the Rosenmund method by selective reduction of the corresponding benzoic acid derivatives, usually using coordinating metal hydrides or using palladium catalysts. These methods have the disadvantage that they use expensive hydride sources or expensive catalysts. In addition, the benzoic acid derivatives used are generally prepared from the corresponding benzonitriles by hydrolysis, therefore, the direct conversion of benzonitriles to benzaldehydes is advantageous. Background technique [0004] US 5124487 pointed out that p-trifluoromethylbenz...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/44C07C47/55
CPCC07C45/44C07C47/55
Inventor M·埃克尔特F·迪尔霍尔茨
Owner BAYER AG
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