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Method for preparing imino ether by virtue of catalytic conversion of aromatic aldehyde

A technology for catalytic conversion and imidate esters, applied in the direction of organic chemistry, etc., can solve the problems of wide application limitation and toxicity of imidate esters, and achieve the effects of high selectivity, high conversion rate, and high product separation yield.

Active Publication Date: 2015-11-04
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because nitrile is a high value-added chemical, it has certain toxicity, so there are great restrictions on the wide application of imidate

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1: with 0.5mmol p-nitrobenzaldehyde, 0.02mmol Co 3 o 4 , 0.20mmolNaOMe1.20mmol ammonia water, 2mL methanol, were added to a 20mL stainless steel reactor with a Teflon liner, filled with 0.1MPa O 2 , kept at 0°C with an ice-water bath, and reacted at this temperature for 100h. The catalyst was removed by suction filtration, the solvent was removed by rotary evaporation, and 5mL H 2 O, was extracted with methanol-ethyl acetate to obtain methyl p-nitrobenzimidate, and the isolated yield was 92%.

Embodiment 2

[0020] Embodiment 2: 0.5mmol p-methoxyl benzaldehyde, 0.10mmol NiO, 0.10mmol NaOMe, 4mmol ammonium bicarbonate, 2mL ethanol is joined in the stainless steel reactor of 20mL band polytetrafluoroethylene liner, fills into 0.3MPa O 2 , heated to 40°C, and reacted at this temperature for 150h. Remove the catalyst by suction filtration, remove the solvent by rotary evaporation, add 5mL H 2 O, extracted with ether to obtain ethyl p-methoxybenzimidate, the separation yield was 80%.

Embodiment 3

[0021] Embodiment 3: with 0.5mmol terephthalaldehyde, 0.15mmol Fe 3 o 4 , 0.15mmolNaOEt, 2mmol ammonium carbonate, and 2mL n-propanol were added to a 20mL stainless steel reactor with a Teflon liner, filled with 0.5MPa O 2 , heated to 60°C, and reacted at this temperature for 50h. Suction filter the catalyst, remove the solvent by rotary evaporation, add 5mL H 2 O, extracted with ethyl acetate-dichloromethane to obtain propyl terephthalimidate with an isolated yield of 84%.

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PUM

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Abstract

The invention provides a method for preparing imino ether by virtue of catalytic conversion of aromatic aldehyde. The method is characterized in that one or two of oxygen gas and air is / are taken as an oxygen source, one or two of ammonia water, ammonia gas, urea and ammonium salt is / are taken as a nitrogen source, and alcohol with low boiling point is taken as a solvent, so that aromatic aldehyde is subjected to an ammoxidation reaction in the presence of a catalyst, and nitrile which is generated in situ and alcohol are subjected to an addition reaction so as to obtain imino ether. The method has the advantages that the raw material utilization ratio is high, the catalyst is easy to recover and recycle, and the separation, purification and derivative conversion of target products are easy.

Description

technical field [0001] The invention relates to the field of conversion of fine chemicals, in particular to a method for preparing imidate by catalytic conversion of aromatic aldehyde under the catalysis of a multifunctional or two-component catalyst with oxidation and acid-base catalysis. Background technique [0002] Based on economic and environmental considerations, multi-step chemical conversion through one-pot reaction has great advantages, which can not only reduce the workload of post-treatment and purification, but also greatly reduce the generation of waste liquid and residue. If heterogeneous catalysts can be used to achieve this conversion from cheap, readily available and non-toxic raw materials, the economic and environmental costs will be further reduced. In recent years, the research on this kind of process has made great progress (Green Chem.2008,10,1029; J.Catal.2008,253; Chem.Rev.2010,111,1072). [0003] Imidate is a widely used intermediate in organic sy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C257/08C07D213/79C07D213/80C07D213/803C07D333/38C07D307/68
Inventor 徐杰贾秀全马继平王敏高进苗虹
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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