Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method of ketoxime

A ketoxime and azole-based technology, applied in the field of preparation of ketoxime, can solve the problems of equipment and environmental impact, large consumption of alkali, large consumption, etc., achieve mild reaction conditions, high product yield and purity, and increase affinity. Effects of nuclear capabilities

Active Publication Date: 2018-06-29
SHAOXING UNIVERSITY
View PDF12 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of ketoxime
  • Preparation method of ketoxime

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] In a three-necked flask, mix benzophenone and hydroxylamine hydrochloride at a molar ratio of 1:1.1-1:1.3, add an appropriate amount of ethanol and stir to completely dissolve it, and then add a certain amount of [P 4444 ][4-CH 3 Im] (the amount of the substance is 10%-50% of the hydroxylamine hydrochloride), heating to reflux, and using thin-layer chromatography (developing solvent: petroleum ether: ethyl acetate = 4:1) to monitor the reaction process. After the reaction, the solvent ethanol was removed by rotary evaporation, an appropriate amount of deionized water was added and stirring was continued, the solid was precipitated, filtered and washed with a small amount of deionized water to obtain a white solid, which was dried under vacuum at 60°C for 24 hours, and the crude yield was 90%; Chromatography (mobile phase acetonitrile:water=7:3, UV detection wavelength at 254nm) determined the purity to be 98% (area normalization method). The structure of benzophenone oxim...

Embodiment 2- Embodiment 23

[0030] The same steps as in Example 1 are used, except for the type and amount of catalyst and the basicity of the oxazolyl anion functionalized ionic liquid, as shown in the following table:

[0031]

[0032] a Compared with the amount of hydroxylamine hydrochloride substance; b HPLC detection, mobile phase acetonitrile: water = 7:3, area normalization method; c It is obtained by multiplying the purity and crude yield.

[0033] As shown in the table, the azole-based anion functionalized ionic liquids all show strong alkalinity, which efficiently catalyzes the reaction of benzophenone and hydroxylamine hydrochloride to prepare benzophenone oxime, and has both the functions of acid binding agent and dehydrating agent. The stronger the basicity, the better the performance of catalyzing the reaction of ketone and hydroxylamine hydrochloride to prepare ketoxime. At the same time, it is found that the alkalinity of the azole-based anion functionalized ionic liquid is mainly related to t...

Embodiment 24

[0034] Example 24 Recycling performance

[0035] Take [P 4444 ][4-CH 3 Im] is the catalyst, the dosage is 20% (mole percentage) of hydroxylamine hydrochloride, the molar ratio of hydroxylamine hydrochloride: benzophenone is 1.2:1, and the reflux reaction is 3.5h with ethanol as the solvent. The yield of benzophenone oxime is the best , Up to 83%.

[0036] The filtrate obtained by separating the solid product after the above reaction was rotary evaporated to remove water and other solvents to obtain [P 4444 ][4-CH 3 Im] Ionic liquid, washed 3 times with ethyl acetate, dried in vacuum at 50°C for 6 hours, and used as a catalyst again to prepare ketoxime by reacting benzophenone with hydroxylamine hydrochloride. After 6 cycles of use, the catalytic effect did not decrease significantly, such as figure 1 Shown.

[0037] In the traditional hydroxylamine hydrochloride to prepare ketoxime, due to NaOH and Na 2 CO 3 Other substances will neutralize with hydrochloric acid, thus losing the p...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
melting pointaaaaaaaaaa
Login to View More

Abstract

The invention belongs to the technical field of ketoxime and specifically relates to a preparation method of ketoxime. The preparation method comprises the following steps: (1) sufficiently mixing ketone and hydroxylamine hydrochloride, adding absolute ethyl alcohol, and stirring till total dissolution to obtain mixed liquid 1; (2) adding imidazolyl anion functionalized ionic liquid into the mixedliquid 1, and heating till ethanol reflux, wherein reaction liquid is obtained after the reaction; (3) removing ethanol in the reaction liquid, adding deionized water and stirring to separate out solid, and performing suction filtration and washing to obtain white solid ketoxime. According to the preparation method provided by the invention, by taking the imidazolyl anion functionalized ionic liquid as a catalyst, a reaction between ketone and hydroxylamine hydrochloride can be efficiently catalyzed, and the preparation method has the advantages of mild reaction conditions, high product yieldand purity and the like.

Description

Technical field [0001] The invention belongs to the technical field of ketoximes, and specifically relates to a preparation method of ketoximes. Background technique [0002] An oxime refers to an organic compound containing a C=N-OH functional group, which is usually produced by the interaction of carbonyl-containing aldehydes and ketones with hydroxylamine. The oxime formed by ketones is called ketoxime. Ketooxime is an important chemical intermediate. It can undergo Beckmann rearrangement reaction to form amides under the action of catalysts such as concentrated sulfuric acid, Lewis acid, solid acid, oxide, molecular sieve, and acidic functionalized ionic liquid. It has been widely used in industry In the production process, for example, the Beckmann rearrangement of cyclohexanone oxime is used in industry to prepare ε-caprolactam, which is the monomer for the synthesis of nylon-6 (Zhou Yun, Lu Jianguo, Zhu Mingqiao. Cyclohexanone oxime Beckmann rearrangement to produce caprol...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C249/08C07C251/48C07C251/44B01J31/24B01J31/02
CPCB01J31/0284B01J31/24B01J31/2404B01J2231/4277C07C249/08C07C251/44C07C251/48
Inventor 许印杰
Owner SHAOXING UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com