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Process for synthesizing nitrocyclohexane by liquid phase nitration

A technology for nitrocyclohexane and liquid-phase nitration, which is applied in the field of acidic ionic liquid catalysts, can solve the problems of difficulty in obtaining high-purity nitrocyclohexane, complicated experimental operations, easy decomposition of catalysts, etc. High catalytic activity, the effect of promoting recycling

Active Publication Date: 2014-02-05
HEBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The main purpose of the present invention is, aiming at the higher reaction temperature existing in the present nitrocyclohexane production technology, the experimental operation is more complicated, it is difficult to obtain high-purity nitrocyclohexane, a large amount of organic solvents need to be used, and the catalyst is easy to decompose , difficulty in synthesis, low catalytic activity, etc.

Method used

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  • Process for synthesizing nitrocyclohexane by liquid phase nitration
  • Process for synthesizing nitrocyclohexane by liquid phase nitration
  • Process for synthesizing nitrocyclohexane by liquid phase nitration

Examples

Experimental program
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Effect test

Embodiment 1

[0025] The synthetic steps of the quaternary ammonium salt acidic ionic liquid catalyst of one-step synthesis:

[0026] In the first step, put 5.91g (0.1mol) trimethylamine aqueous solution in a 100mL three-necked flask, and slowly add 10.0g (0.1mol) concentrated sulfuric acid (98%) dropwise in an ice-water bath (below 5°C), and the dropwise addition is completed Then continue to stir for 1h.

[0027] In the second step, the temperature of the reaction solution in the first step was raised to 80° C. and stirred for 4 hours.

[0028] In the third step, the crude product obtained in the second step is cooled to room temperature, washed three times with ethyl acetate, and the ethyl acetate and the like are removed by rotary evaporation under reduced pressure, and then vacuum-dried at 80°C for 12 hours to obtain a colorless, transparent and viscous Ionic liquid a: trimethylamine bisulfate ionic liquid ([(CH 3 ) 3 N]HSO 4 ). See the compound (I) for the structural formula, R ...

Embodiment 2

[0030] Step is with embodiment 1, difference is, in the first step, add 10.1g (0.1mol) triethylamine aqueous solution, the 3rd step obtains yellow viscous solid b: triethylamine bisulfate ionic liquid ([(CH 3 CH 2 ) 3 N]HSO 4 ). See the compound (I) for the structural formula, R 1 =C 2 h 5 , Y 1 =HSO 4 .

Embodiment 3

[0032] Step is the same as Example 1, and the difference is that in the first step, 8.21g (0.1mol) N-methylimidazole is added, and the third step obtains yellow transparent viscous liquid c: N-methylimidazole bisulfate ionic liquid ([ Hmim] HSO 4 ). See compound (Ⅱ) for structural formula, Y 1 =HSO 4 .

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Abstract

The invention discloses a process for synthesizing nitrocyclohexane by liquid phase nitration. The process comprises the following steps: feeding cyclohexane, nitric acid, distilled water and an acidic ionic liquid catalyst into a high-pressure reaction kettle, wherein the mole ratio of the cyclohexane to the nitric acid to the distilled water to the acidic ionic liquid catalyst is 1:1:12:(0.025-0.1), the reaction temperature is 115-135 DEG C, the reaction time is 6-24 hours, and the nitrocyclohexane is finally prepared. The mass percentage of the nitric acid is 65-68%. The acidic ionic liquid catalyst is a quaternary ammonium salt acidic ionic liquid catalyst which is prepared from a tertiary amine compound and acid in a one-step neutralization synthesis mode, or is a functionalized quaternary ammonium salt acidic ionic liquid catalyst which is synthesized from the tertiary amine compound and the acid in alkylation and neutralization two-step synthesis modes. The acidic ionic liquid catalyst for synthesizing the nitrocyclohexane from cyclohexane by liquid phase nitration has high catalysis activity, and meanwhile the function of a phase transfer catalyst is achieved, the reaction temperature is low, and no organic solvents are added.

Description

technical field [0001] The invention relates to the synthesis of nitrocyclohexane, in particular to an acidic ionic liquid catalyst for liquid-phase nitration of cyclohexane to synthesize nitrocyclohexane and its preparation and application. technical background [0002] Nitrocyclohexane is an important chemical intermediate and organic solvent. Because of its unique reactivity and physicochemical properties, it has become an important raw material in the field of fine chemicals such as pharmaceuticals, surfactants, solvents, lubricants and emulsifiers, and Nearly two thousand derivatives can be produced. Cyclohexylamine can be generated by complete hydrogenation of nitrocyclohexane, and cyclohexanone oxime can be reduced by partial hydrogenation. The former is an important raw material for the synthesis of chemical products such as medicine, fuel, and dyes; the latter can be rearranged by Beckmann to generate caprolactam, which can also be used to produce nylon fibers and ...

Claims

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Application Information

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IPC IPC(8): C07C205/05C07C201/08B01J31/02
Inventor 王荷芳王媛媛王延吉贾立元刘红涛
Owner HEBEI UNIV OF TECH
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