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Method for removal of oxime from aldoxime or ketoxime

A technology of ketoxime and aldoxime, applied in the field of purification of aldehyde or ketone, can solve the problems of unenvironmental protection, uneconomical and the like, and achieve the effect of reaction cleaning

Active Publication Date: 2017-03-08
YANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the current deoxime technology for aldoxime or ketoxime requires the use of a large amount of metal or non-metallic chemical oxidants, halogenated or nitro solvents or additives, and expensive metal catalysts, so it is neither environmentally friendly nor economical.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Mix 1 mmol of benzaldoxime, 0.025 mmol of dibenzyldiselenide, 0.45 mmol of hydrogen peroxide and 2 mL of petroleum ether, then heat at 60°C in air for 24 hours, and separate by column chromatography to obtain benzaldehyde in a yield of 88 %.

Embodiment 2

[0016] Embodiment 2: Other conditions are the same as in Embodiment 1, and the reactions of different organoselenium catalysts are tested, and the experimental results are shown in Table 1.

[0017] The inspection of different organic selenium catalysts in table 1

[0018] serial number Organoselenium catalyst Benzaldehyde yield / % 1 Benzene selenite 21 2 diphenyl diselenide 18 3 Di-n-butyl diselenide 0 4 2-p-trifluoromethylphenyl diselenide 10 5 Di-3,5-ditrifluoromethylphenyl diselenide 6 6 Di-m-fluorophenyl diselenide 16 7 benzyl selenous acid 90 5 Dibenzyl diselenide 88 (Example 1)

[0019] From the above results, it can be seen that benzyl selenous acid and dibenzyl diselenide as catalysts have special effects on the reaction, while other selenium catalysts have no obvious effect.

Embodiment 3

[0020] Example 3: Other conditions are the same as in Example 1, and the reactions of different molar ratios of organic selenium catalysts and oximes are tested, and the experimental results are shown in Table 2.

[0021] The inspection of the mixing molar ratio of different organic selenium catalysts and oxime of table 2

[0022] Mixing molar ratio of organoselenium catalyst to oxime 1:100 2:100 2.5:100 4:100 6:100 Benzaldehyde yield / % 71 84 88 (Example 1) 83 75

[0023] From the above results, it can be known that the mixing molar ratio of organoselenium catalyst and oxime is 2.5:100, which has the best effect (Example 1).

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PUM

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Abstract

The invention discloses a method for removal of oxime from aldoxime or ketoxime and relates to the technical field of purification of aldehydes or ketones. The method adopts organic selenium as a catalyst, hydrogen peroxide as an auxiliary agent and air as oxidant in a solvent to carry out an aldoxime or ketoxime reaction process only by heating so that a deoximation product such as aldehyde or ketone is obtained. The method utilizes a clean reaction process and is suitable for large-scale production.

Description

technical field [0001] The invention relates to the technical field of purification of aldehydes or ketones. Background technique [0002] my country is rich in selenium resources, and it is of great strategic significance to develop new applications of selenium resources, which can repeatedly play the resource advantages of our country. Selenium is an essential trace element for the human body, has certain biological activity, and is widely used in the field of medicine. Selenium compounds have good catalytic activity and can catalyze a series of green synthetic reactions with industrial application value. [0003] The study found that the deoxime reaction is an important reaction in organic synthesis. Oximes are stable, therefore, oximation-deoxime strategies can be used for the protection, identification and purification of aldehydes or ketones. And many oximes can be synthesized from non-carbonyl compounds (such as avronone oxime), therefore, the deoxime reaction can ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/00C07C47/54C07C49/78C07C47/542C07C47/546C07C47/55C07C49/76C07C49/67C07C49/813C07C49/84C07C49/784C07C49/786C07C49/807C07C201/12C07C205/44C07C205/45C07D333/22
CPCC07C45/00C07C201/12C07D333/22C07C47/54C07C49/78C07C47/542C07C47/546C07C47/55C07C49/76C07C49/67C07C49/813C07C49/84C07C49/784C07C49/786C07C49/807C07C205/44C07C205/45
Inventor 俞磊张昊袁丹丹景崤壁
Owner YANGZHOU UNIV