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A kind of method that catalyzes cyclohexanone oxime hydrolysis reaction in acidic ionic liquid

An acidic ionic liquid, cyclohexanone oxime technology, applied in chemical instruments and methods, preparation of organic compounds, catalysts for physical/chemical processes, etc. , Overcome the effect of corrosion equipment

Inactive Publication Date: 2015-08-19
HEBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This process route overcomes the environmental pollution caused by the use of inorganic strong acid catalysts in the traditional cyclohexanone oxime hydrolysis process, the shortcomings of difficult recovery of inorganic acids, and the shortcomings of using metal chlorides in the existing ionic liquid catalytic process

Method used

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  • A kind of method that catalyzes cyclohexanone oxime hydrolysis reaction in acidic ionic liquid
  • A kind of method that catalyzes cyclohexanone oxime hydrolysis reaction in acidic ionic liquid
  • A kind of method that catalyzes cyclohexanone oxime hydrolysis reaction in acidic ionic liquid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The molecular structure of the N,N,N-trimethyl-N-sulfobutyl ammonium bisulfate ionic liquid described in this embodiment is as follows:

[0024]

[0025] Referring to the synthesis method reported in the literature (Acta Chemical Society, 2009, 60(2): 345-350), equimolar trimethylamine aqueous solution (≥33%) and 1,4-butane sultone were added to the reaction flask, and React in a water bath at 50°C for 12 hours to obtain a white solid; add equimolar concentrated sulfuric acid (≥98.0%) after purification and drying, react in a water bath at 80°C for 4 hours to obtain a colorless or light yellow transparent liquid, wash with ether, and dry in vacuo Then the target ionic liquid is obtained.

Embodiment 2

[0027] The molecular structure of the N,N,N-trimethyl-N-sulfobutyl trifluoromethanesulfonate ionic liquid described in this example is as follows:

[0028]

[0029] Same as the operating steps and reaction conditions of Example 1, just after the purification and drying steps, the original step of "adding equimolar concentrated sulfuric acid" is replaced by "adding equimolar trifluoromethanesulfonic acid", after the reaction is completed, The target ionic liquid was obtained by washing with ether and drying in vacuum.

Embodiment 3

[0031] The molecular structure of the 1-sulfobutyl-3-methylimidazolium trifluoromethanesulfonate ionic liquid described in this example is as follows:

[0032]

[0033] Referring to the synthesis method reported in the literature (Chinese Journal of Chemical Engineering, 2009, 17(5):756-760), equimolar 1-methylimidazole and 1,4-butane sultone were added to the reaction flask, and React in a water bath at 40°C for 12 hours to obtain a white solid; add equimolar trifluoromethanesulfonic acid after purification and drying, and react in a water bath at 80°C for 6 hours to obtain a colorless or light yellow transparent liquid, which is washed with ether and dried in vacuum. to obtain the target ionic liquid.

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Abstract

The invention discloses a method for catalyzing a hydrolysis reaction of cyclohexanone-oxime in acidic ionic liquid. The method comprises the following steps of: placing the cyclohexanone-oxime in a reactor, adding an acidic ionic liquid catalyst and deionized water; carrying out constant-temperature stirring reaction for 0.15-4h under the conditions of normal pressure and a temperature of 10-80 DEG C, and separating an organic phase from an inorganic phase in reaction liquid to respectively obtain cyclohexanone and hydroxylamine, wherein the acidic ionic liquid is SO3H-type ionic liquid, the material ratio, namely a mol ratio of the cyclohexanone-oxime to the ionic liquid is 1:(0.16-5.4), and the mol ratio of the deionized water to the ionic liquid is (11-369):1. The method for catalyzing the hydrolysis reaction of the cyclohexanone-oxime in the acidic ionic liquid uses the SO3H-type ionic liquid as a catalyst of the hydrolysis reaction of the cyclohexanone-oxime. Compared with the existing cyclohexanone-oxime hydrolysis route, the method has the advantages that the acidic ionic liquid can be recycled, and the transform ratio of the cyclohexanone-oxime is close to 100 percent.

Description

technical field [0001] The present invention relates to a kind of method of deoximation reaction, specifically a kind of 3 The invention discloses a new method for directly catalyzing the hydrolysis reaction of cyclohexanone oxime in an H-type acidic ionic liquid, belonging to the field of organic chemical reaction methods. Background technique [0002] The hydrolysis reaction process of cyclohexanone oxime is shown in formula (1). This reaction can not only generate cyclohexanone, but also obtain hydroxylamine product at the same time. The products obtained from the reaction are all important chemical raw materials. For example, cyclohexanone is mainly used in the synthesis of nylon and adipic acid, as well as in industries such as paints, pesticides, and dyes; hydroxylamine has a wide range of uses in the synthesis of caprolactam, pesticides, and medicine ( Fine and Specialty Chemicals, 2007, 15(16): 18-21; Progress in Chemical Industry, 2012, 31(9): 2043-2048). In addit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/403C07C45/51C01B21/14B01J31/02
Inventor 王延吉张东升徐元媛檀学军张广林陈英曼高丽雅赵新强
Owner HEBEI UNIV OF TECH
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