Environment-friendly method for preparing adipic acid by catalytic oxidation

A technology of catalytic oxidation and adipic acid, applied in chemical instruments and methods, preparation of organic compounds, preparation of carboxylate, etc., can solve the problems of difficulty in showing catalytic activity, high reaction temperature, long reaction time, etc., and achieves remarkable results. Catalytic activity, simple preparation method, and the effect of improving the problem of serious deactivation

Active Publication Date: 2012-12-12
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When nano-gold catalysts are used to produce adipic acid in a one-step method of cyclohexane, because of the long reaction time and high reaction temperature, it is difficult for nano-gold catal

Method used

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  • Environment-friendly method for preparing adipic acid by catalytic oxidation
  • Environment-friendly method for preparing adipic acid by catalytic oxidation
  • Environment-friendly method for preparing adipic acid by catalytic oxidation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 74mmol cyclohexane, 7ml solvent butanone (the mass ratio of cyclohexane to butanone is 1.1:1), 33mg activated carbon-supported nano-gold catalyst (the mass fraction of Au is 1.25%; the mass fraction of cyclohexane and catalyst Ratio is 188.7:1), 0.7mmol initiator cyclohexanone (mass ratio of cyclohexane to cyclohexanone is 90.6:1), magnetic stirrer, turn on magnetic stirring, and at 130°C, feed oxygen to maintain oxygen pressure At 1.5MPa, react for 8 hours and then cool to room temperature. Activated carbon-supported nano-gold catalyst and reaction solution were obtained by centrifugation, a small part of the reaction solution was used for the result detection, and the remaining part of the reaction solution was extracted three times with deionized water to obtain an oil phase and a water phase, and the water phase was cooled at 0°C for 12 Hours, adipic acid crystalline solids were obtained; the oil phase was vacuum rotary evaporated, the initiator cyclohexanone wa...

Embodiment 2~ Embodiment 8

[0035] Add 74mmol cyclohexane, 7ml methyl ethyl ketone, 33mg catalyst (1.5% gold by weight), 0.7mmol cyclohexanone and a magnetic stirring bar into the reaction kettle, and start the magnetic stirring. At 130° C., feed oxygen to maintain the oxygen pressure at 1.5 MPa, react for 8 hours and then cool to room temperature. Product separation and analysis methods are the same as in Example 1. In Examples 2-8, the mass fractions of gold in the catalysts were 0.5%, 0.75%, 1.0%, 1.25%, 1.5%, 2.0%, and 2.5%, respectively. The cyclohexane conversion and adipic acid selectivity are shown in Table 1.

[0036] Table 1 Quantitative analysis results of Examples 2 to 8 a

[0037]

[0038]a Reaction conditions: 74mmol cyclohexane, 33mg catalyst (1.5% Au), 7ml butanone, 0.7mmol cyclohexanone, 130°C, 1.5MPa, 8h

[0039] b KA oil: Cyclohexanol and cyclohexanone are collectively called KA oil

Embodiment 9~ Embodiment 13

[0041] Add 74mmol cyclohexane, 7ml methyl ethyl ketone, 33mg catalyst (gold mass percentage is 1.5%), 0.7mmol cyclohexanone and a magnetic stirrer to the reaction kettle, turn on the magnetic stirrer, and at a certain temperature, feed oxygen to maintain oxygen The pressure was 1.5MPa, and it was cooled to room temperature after 8 hours of reaction. Product separation and analysis methods are the same as in Example 1. In Examples 9 to 13, the reaction temperatures were 100°C, 120°C, 130°C, 140°C, and 150°C, respectively. The cyclohexane conversion and adipic acid selectivity are shown in Table 2.

[0042] Table 2 embodiment 9 ~ 13 quantitative analysis results a

[0043]

[0044] a Reaction conditions: 74mmol cyclohexane, 33mg catalyst (1.5% Au), 7ml butanone, 0.7mmol cyclohexanone, 1.5MPa, 8h

[0045] b KA oil: Cyclohexanol and cyclohexanone are collectively called KA oil

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Abstract

The invention discloses an environment-friendly method for preparing adipic acid by catalytic oxidation. The method includes: at the beginning of reaction, adding cyclohexane, butanone serving as solvent, cyclohexanone serving as initiators and activated carbon supported nano-gold catalysts into a stainless steel high-pressure reactor; carrying out the catalytic oxidation reaction for 3-14 hours under the pressure of 0.9-2.1MPa at the temperature of 100-150 DEG C; separating after the reaction is completed to obtain the activated carbon supported nano-gold catalysts and reaction liquor, and processing the reaction liquor to obtain adipic acid crystalline solid; collecting the cyclohexanone serving as the initiators by oil-phase vacuum rotary steaming; and washing and drying the activated carbon supported nano-gold catalysts for recycling. By the method, solvent effect of the butanone serving as the solvent is particularly suitable for the nano-gold catalysts to catalyze the cyclohexane to generate the adipic acid by means of selective oxidation, and the problems of low activity and proneness to inactivation of the catalysts in reaction are solved. The method is simple in technological process, convenient for preparing and separating the catalysts, mild in reaction conditions, low in technological cost, economic, efficient and environment-friendly and pollution-free as molecular oxygen substitutes for nitric acid to be used as oxidants.

Description

technical field [0001] The invention relates to an environment-friendly catalytic oxidation method for preparing adipic acid. Background technique [0002] As an important organic intermediate and raw material, adipic acid is widely used in chemical, pharmaceutical, food and other industrial fields, and the industrial demand is huge. The existing adipic acid production process is mainly a two-step cyclohexane oxidation method, which requires the use of nitric acid as an oxidant, and the nitrogen oxides produced during the process have caused serious environmental pollution. In order to replace the nitric acid oxidation method, domestic and foreign scholars have done a lot of research work on the one-step catalytic oxidation of adipic acid, but it is still urgent to find a process that can take into account environmental protection, high efficiency and low cost. [0003] In recent years, in order to improve the conversion rate and selectivity of the one-step adipic acid prod...

Claims

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Application Information

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IPC IPC(8): C07C55/14C07C51/215
Inventor 朱明乔戴欢
Owner ZHEJIANG UNIV
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