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A kind of preparation method of ketoxime

A technology of ketoxime and ionic liquid, applied in the field of ketoxime, can solve the problems of large alkali consumption, equipment and environmental impact, large consumption, etc., achieve high product yield and purity, mild reaction conditions, and increase nucleophilic ability Effect

Active Publication Date: 2021-08-27
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The above-mentioned alkaline substances will neutralize with the hydrochloric acid in hydroxylamine hydrochloride during the reaction process, and the consumption is relatively large, and the large amount of salt produced will easily affect the equipment and the environment
Therefore, when using the traditional hydroxylamine hydrochloride method to prepare ketoxime, there are disadvantages such as large alkali consumption (the molar ratio of alkali: hydroxylamine hydrochloride is 1.5:1-1:1), and it is not easy to recycle and use, and it is easy to cause environmental pollution.

Method used

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  • A kind of preparation method of ketoxime
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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] In the three flasks, diphenyl ketone and hydroxylamine hydroxylamine were mixed by 1: 1.1-1: 1.3, and the appropriate amount of ethanol was added to completely dissolve, then add a quantity [p 4444 ] [4-ch 3 IM] (the amount of substance is 10% -50% of hydroxylamine hydrochloride), heated reflux, using thin layer chromatography (the opening agent as petroleum ether: ethyl acetate = 4: 1) Monitor the reaction process. After the reaction, the solvent ethanol is rotated, and the appropriate amount of deionized water is added, stirring, precipitating the solid, filtered and washed with a small amount of deionized water, to give a white solid, 60 ° C drying 24 h, 20%; The chromatography (mobile phase acetonitrile: water = 7: 3, UV detection wavelength is 254 nm) to determine the purity of 98% (area belonging). It is characterized by IR, NMR and MS, which is de-amphenylphenyl oxime, and melting melting point MP: 143.1-143.8 ° C.

Embodiment 2- Embodiment 23

[0030]The same embodiments are used in Example 1, which distinguishes that the catalyst type and amount, azole anionic ion-functional ionic liquid alkali is as shown in the following table:

[0031]

[0032] a Compared to the amount of hydroxylamine substance of hydrochloride; b HPLC detection, mobile phase acetonitrile: water = 7: 3, area belonging; c It is obtained based on purity and crude yield.

[0033] As indicated, the azole anion-functionalized ionic liquid has a strong alkaline, efficiently catalyzed diphenyl ketone and hydrochloride reaction to prepare diphenylphenyl oxime, combined with the acid and dehydrated agent. The stronger the alkaline is, and the hydroxylamine reaction of hydroxylamine is better than the hydrochloride reaction. At the same time, the alkalineness of the azol-based anion functionalized ionic liquid is found is mainly related to the type and push of the anion, and the electron absorption is less affected by the cation. NAAc, NA with traditional h...

Embodiment 24

[0034] Example 24 Cycling Performance

[0035] [P 4444 ] [4-ch 3 IM] is a catalyst, 20% (mole percent) of hydroxylamine hydrochloride, hydroxylamine hydrochloride: a molar ratio of 1.2: 1, refluxed with ethanol for a solvent 3.5H, and diphenyl ketoxime yield optimal Can reach 83%.

[0036] The filtrate obtained by separating the solid product after the reaction is separated, rotationally evaporated to remove water, resulting in [P 4444 ] [4-ch 3 Im] Ion liquid, then washed 3 times with ethyl acetate, dried in vacuo at 50 ° C, and used as a catalyst for dibenzophenone and hydroxylamine hydrochloride to prepare ketoxime. After the cycle is used 6 times, the catalytic effect has not shown significant decline, such as figure 1 Indicated.

[0037] When preparing ketone oxime in conventional hydroxylamine, due to NaOH and NA 2 CO 3 The substance is neutralized with hydrochloric acid, thereby losing the cycling performance. The azol-based anion-functionalized ionic liquid used in the pre...

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Abstract

The invention belongs to the technical field of ketoxime, and specifically relates to a preparation method of ketoxime. The preparation method follows the following steps: step 1, fully mix ketone and hydroxylamine hydrochloride, add absolute ethanol and stir until completely dissolved, and obtain a mixed solution 1; Step 2, add the azole-based anion functionalized ionic liquid to the mixed solution 1, heat to ethanol reflux; obtain the reaction solution after the reaction; step 3, remove the ethanol in the reaction solution, add deionized water and stir to precipitate Solid, obtained white solid-ketoxime after suction filtration and washing. The invention uses the azole-based anion functionalized ionic liquid as a catalyst, can efficiently catalyze the reaction of ketone and hydroxylamine hydrochloride, and has the advantages of mild reaction conditions, high product yield and purity, and the like.

Description

Technical field [0001] The present invention belongs to the field of ketoxime, and is, according to the field of ketime. Background technique [0002] The oxime is an organic compound containing a C = N-OH functional group, which is usually produced by an aldehyde containing a carbonyl group, a ketone compound to a hydroxylamine, wherein the ketime is ketone formed from the ketone. Ketobime is an important chemical intermediate that produces beckmann rearrangement reactive amide under concentrated sulfuric acid, Lewis acid, solid acid, oxide, molecular sieve, acid-based, ionic liquid, etc., has been widely used in industrial Production process, such as the use of cyclohexanone oxime, beckmann rearrangement, ε-caprolactam, is a monomer synthesis nylon-6 (Zhou Yun, Lu Jianguo, Zhu Mingqiao. Cyclohexanone Bakerman Rearranged Heracanoamide Green Catalysis Research progress, synthetic fiber industry, 2015, 38 (2): 51-56). At the same time, ketobime can also be formed by sodium mercury...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C249/08C07C251/48C07C251/44B01J31/24B01J31/02
CPCB01J31/0284B01J31/24B01J31/2404B01J2231/4277C07C249/08C07C251/44C07C251/48
Inventor 许映杰
Owner SHAOXING UNIVERSITY
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