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Method for co-producing adipic acid and cyclohexanone-oxime from cyclohexane

A technology of cyclohexanone oxime and cyclohexane, which is applied in the field of preparation of adipic acid or cyclohexanone oxime, can solve the problems of high energy consumption, difficulty in realizing large-scale production, serious environmental pollution, etc., and achieves low material consumption and energy consumption , strong environmental friendliness, environmental friendly effect

Active Publication Date: 2021-06-11
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0023] In view of the problems existing in the above-mentioned prior art, especially problems such as high energy consumption in industrial applications, serious environmental pollution, and difficulty in realizing large-scale production, the present invention provides a co-production of adipic acid and cyclohexane that can realize efficient industrial applications. The method of ketoxime, the process is simple and efficient, and environmentally friendly

Method used

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  • Method for co-producing adipic acid and cyclohexanone-oxime from cyclohexane
  • Method for co-producing adipic acid and cyclohexanone-oxime from cyclohexane
  • Method for co-producing adipic acid and cyclohexanone-oxime from cyclohexane

Examples

Experimental program
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Effect test

Embodiment 1

[0101] Embodiment 1: adopt fixed bed gas phase continuous reaction process. The liquid cyclohexane is input by the metering pump, and after being vaporized in the preheating section, the cyclohexane:NO 2 The molar ratio of 0.2:1, cyclohexane and NO 2 The mixture passes through a glass tube reactor with an inner diameter of φ10, which is filled with a V with a height of about 10 cm 2 o 5 / MCM-41 catalyst; the temperature of the reactor is controlled at 180°C, and the outlet gas of the reactor is condensed through a glass condenser tube with a cooling jacket and then evacuated (the circulating cooling water is kept at a constant temperature of 5°C); after 2 hours of stable operation of the reaction system Start timing and collect condensed products, stop feeding cyclohexane and NO to the reactor after 24 hours of continuous operation 2 ; After the reaction system is cooled to normal temperature, the product sticking to the outlet of the reactor and the wall of the condenser t...

Embodiment 2

[0103] Embodiment 2: reaction step is the same as example 1, and difference is, also pass into O simultaneously in the reaction process 2 , making cyclohexane:NO 2 :O 2 The molar ratio is 0.8:1:0.1. According to the analysis result and material balance to whole liquid phase and solid phase product, the transformation rate of cyclohexane is 35.7%, and the selectivity of adipic acid and nitrocyclohexane is respectively 50.2% and 48.4% (both total selection sex is 98.6%). Finally, nitrocyclohexane with a purity of 98.4% and adipic acid with a purity of 99.5% were obtained by separating and purifying the liquid and solid phases.

Embodiment 3

[0104] Embodiment 3: The operating steps are the same as in Example 1, except that no catalyst is used. According to the analysis result and material balance to whole liquid phase and solid phase product, the transformation efficiency of cyclohexane is 9.7%, and the selectivity of adipic acid and nitrocyclohexane is respectively 34.1% and 58.4% (both total selections sex is 92.5%). Finally, nitrocyclohexane with a purity of 98.2% and adipic acid with a purity of 99.6% were obtained by separating and purifying the liquid and solid phases.

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Abstract

The invention relates to a method for co-producing adipic acid and cyclohexanone-oxime from cyclohexane. The method comprises the following steps: (1) carrying out oxidation nitration on cyclohexane and NOx to generate adipic acid, nitrocyclohexane, nitrogen oxides and a byproduct-A, and separating to obtain crude adipic acid and nitrocyclohexane; (2) carrying out catalytic hydrogenation on the obtained nitrocyclohexane and hydrogen to generate cyclohexanone-oxime and a small amount of cyclohexylamine, separating to obtain crude cyclohexanone-oxime and cyclohexylamine, and enabling cyclohexylamine to be directly used as a byproduct or to be continuously converted into cyclohexanone-oxime. and (3) partially oxidizing the cyclohexylamine obtained in the previous step with molecular oxygen to obtain an oxidation reaction product consisting of cyclohexanone-oxime, a byproduct B and possibly unconverted cyclohexylamine, and then separating the oxidation reaction product without separation, or firstly separating part or all of water in the oxidation reaction product, carrying out hydrogenation amination reaction under the action of a catalyst, or carrying out hydrogenation and amination reaction, or only carrying out hydrogenation reaction, and then separating to obtain the cyclohexanone-oxime. The method can realize high-selectivity co-production of adipic acid and cyclohexanone-oxime, and is short in process flow, low in equipment investment and low in material consumption, energy consumption and cost.

Description

technical field [0001] The invention relates to a method for preparing adipic acid or cyclohexanone oxime, in particular to a method for coproducing adipic acid and cyclohexanone oxime from cyclohexane. Background technique [0002] Adipic acid (ADA), commonly known as fatty acid, is a very important industrial material and intermediate, mainly used in the manufacture of nylon 66, plasticizers, greases, pesticides and adhesives. [0003] Cyclohexanone oxime is an intermediate of ε-caprolactam, an important raw material (the main purpose is to produce polyamide chips through polymerization to further produce nylon fibers, engineering plastics, plastic films, etc.). [0004] At present, the industrial production of adipic acid generally adopts a two-step oxidation method using cyclohexane as a raw material: first, KA oil (a mixture of cyclohexanone and cyclohexanol) is obtained by air oxidation of cyclohexane, and then KA oil is used as a The raw material is oxidized with nit...

Claims

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Application Information

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IPC IPC(8): C07C51/27C07C55/14C07C249/04C07C251/44C07C249/10
CPCC07C51/27C07C201/08C07C249/10C07C249/04C07C2601/14C07C55/14C07C205/05C07C251/44Y02P20/30C07C51/316C07C51/347C07C2523/22
Inventor 罗和安游奎一蹇建刘平乐倪文金艾秋红
Owner XIANGTAN UNIV
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