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Method for preparing hydroxylamine by catalyzing cyclohexanone-oxime through cross-linked acidic polymeric ionic liquid

A technology for polymerizing ionic liquid and cyclohexanone oxime, applied in chemical instruments and methods, hydroxylamine, organic compound/hydride/coordination complex catalyst, etc., can solve product separation, equipment corrosion, cyclohexanone oxime conversion rate Low problems, to achieve the effect of easy separation, easy separation and recovery, and easy recycling

Active Publication Date: 2022-05-13
HEBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The invention solves the problems of equipment corrosion and product separation when liquid acids (hydrochloric acid, sulfuric acid, acidic ionic liquid, etc.) are used as catalysts; when solid acids such as HZSM-5 and loaded ionic liquids are used as catalysts, the There is the problem of low conversion rate of cyclohexanone oxime

Method used

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  • Method for preparing hydroxylamine by catalyzing cyclohexanone-oxime through cross-linked acidic polymeric ionic liquid
  • Method for preparing hydroxylamine by catalyzing cyclohexanone-oxime through cross-linked acidic polymeric ionic liquid
  • Method for preparing hydroxylamine by catalyzing cyclohexanone-oxime through cross-linked acidic polymeric ionic liquid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] (1) At 80°C, N 2 Under protection, 0.1moL of 1-vinylimidazole (V) and 0.1moL of 1,4-butane sultone (BS) were dissolved in 80mL of acetonitrile, placed in the reactor, and mechanically stirred for 36h. After the reaction , washed the product with acetonitrile, and dried in vacuum at 80° C. for 10 h to obtain the intermediate salt of the polymerized ionic liquid monomer (VBS). (2) At 80°C, N 2 Under protection, 5g of polymerized ionic liquid monomer intermediate salt (VBS), azobisisobutyronitrile, and divinylbenzene (DVB) were dissolved in 60mL of ethanol, placed in the reactor, and mechanically stirred for 8h, wherein the molar ratio Polymerized ionic liquid monomer intermediate salt (VBS), divinylbenzene (DVB)=1:2, azobisisobutyronitrile is 3% of the mass of polymerized ionic liquid monomer intermediate salt (VBS). After the reaction, the product was washed with ethanol and vacuum-dried at 80° C. for 10 h to obtain Poly(VBS-DVB). (3) At 70°C, N 2 Under protection, d...

Embodiment 2

[0043] Poly(VBS-MBA)HSO 4 The other steps of the preparation method are the same as in Example 1, the difference is that divinylbenzene (DVB) is replaced by N,N'-methylenebisacrylamide (MBA) and the sulfuric acid solution is replaced by trifluoromethanesulfonic acid , can also be obtained in the same way as the above steps, Poly(VBS-DVB)SO 3 CF 3 , Poly(VBS-MBA)SO 3 CF 3 .

[0044] The Poly(VBS-MBA)HSO 4 The structural formula of is as follows:

[0045]

[0046] Among them, 2≤n 4 ≤2000, 2≤n 5 ≤2000, 2≤n 6 ≤2000.

[0047] The Poly(VBS-DVB)SO 3 CF 3 The structural formula of is as follows:

[0048]

[0049] Among them, 2≤n 1 ≤2000, 2≤n 2 ≤2000, 2≤n 3 ≤2000.

[0050] The Poly(VBS-MBA)SO 3 CF 3 The structural formula of is as follows:

[0051]

[0052] Among them, 2≤n 4 ≤2000, 2≤n 5 ≤2000, 2≤n 6 ≤2000.

Embodiment 3

[0054] Cyclohexanone oxime (0.5g-0.0044mol), deionized water (30mL-1.67mol), catalyst Poly(VBS-DVB)HSO 4 (2g) was placed in a 100mL eggplant-shaped bottle, and the reaction was completed after magnetic stirring for 1 hour under normal pressure at 60°C. Centrifuge to recover the polymerized ionic liquid catalyst at the bottom; extract and separate the reaction liquid at the top with dichloroethane to obtain the organic phase cyclohexanone and the aqueous phase hydroxylamine solution respectively. The content of cyclohexanone in the organic phase was analyzed by gas chromatography, the conversion rate of cyclohexanone oxime was quantitatively calculated, and the yield of hydroxylamine in the aqueous phase was analyzed by titration.

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Abstract

The invention relates to a method for preparing hydroxylamine by catalyzing cyclohexanone oxime through cross-linked acidic polymeric ionic liquid. The method comprises the following steps: putting cyclohexanone-oxime into a reactor, and adding cross-linked acidic polymeric ionic liquid and deionized water; stirring at a constant temperature of 10-80 DEG C under normal pressure for 0.1-3 hours, centrifugally separating the catalyst, adding a dichloroethane extracting agent, and extracting and separating to obtain an organic phase cyclohexanone and a raffinate water phase which is a hydroxylamine water solution. Compared with a traditional homogeneous catalyst, the cross-linked acidic polymeric ionic liquid is easy to separate from reactants and products, convenient to recycle and excellent in catalytic performance.

Description

technical field [0001] The invention relates to a method for preparing hydroxylamine by removing oxime, in particular to a method for preparing hydroxylamine by hydrolysis of cyclohexanone oxime catalyzed by a cross-linked acidic polymeric ionic liquid. Background technique [0002] The hydrolysis reaction process of cyclohexanone oxime is shown in formula (I), and the cyclohexanone and hydroxylamine produced by this reaction are important chemical raw materials. Cyclohexanone is mainly used as a raw material and solvent for organic synthesis in industry. For example, it can be used as an intermediate in the synthesis of caprolactam and adipic acid, and can be used as a solvent to dissolve nitrocellulose, coatings, paints, etc. In addition, another product of this reaction, hydroxylamine, is an important class of chemical raw materials. It is usually used as a reducing agent in organic synthesis, and condenses with carbonyl compounds to form oximes. It is mainly used for the...

Claims

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Application Information

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IPC IPC(8): C01B21/14B01J31/06B01J31/10
CPCC01B21/1454B01J31/06B01J31/10Y02P20/54
Inventor 张东升赵山山王双瑜程鹏王延吉李志会杨秋生
Owner HEBEI UNIV OF TECH
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