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Method for preparing suberic acid through cyclooctene oxidation

A technology of cyclooctene and suberic acid, which is applied in the field of catalyzing the oxidation of cyclooctene to prepare important chemical suberic acid, can solve the problems of low product selectivity and low yield, achieve high selectivity, reduce costs, and guarantee The effect of the catalytic effect

Active Publication Date: 2014-01-29
LIAONING UNIVERSITY OF PETROLEUM AND CHEMICAL TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this reaction process is not suitable for the oxidation of cyclooctene, and the yield of suberic acid obtained by oxidation of cyclooctene is lower than 10%, and the product selectivity is very low

Method used

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  • Method for preparing suberic acid through cyclooctene oxidation
  • Method for preparing suberic acid through cyclooctene oxidation
  • Method for preparing suberic acid through cyclooctene oxidation

Examples

Experimental program
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Effect test

Embodiment 1

[0018] Embodiment 1: the method for preparing suberic acid by oxidation of cyclooctene

[0019] (1) Preparation of tetramethylammonium perrhenate

[0020] Tetramethylammonium bromide and KOH were mixed and dissolved in a certain amount of absolute ethanol solution at a molar ratio of 1:1.1, stirred and reacted at room temperature for 12 hours, white potassium bromide was precipitated, and the potassium bromide precipitate was removed by filtration to obtain Ethanol solution of tetramethyl quaternary ammonium base. In the obtained ethanol solution of tetramethylquaternary ammonium base, NH was added in a molar ratio of 1:1.1 4 ReO 4 , heated to 80°C, ammonia gas was released, heated to reflux until no ammonia gas was released, then lowered the temperature to room temperature, stirred for 24 hours, filtered to remove excess ammonium perrhenate, and the filtrate was distilled and concentrated by a rotary evaporator to obtain crystals. Suction filtration and vacuum drying at 40...

Embodiment 2

[0025] Embodiment 2: the method for preparing suberic acid by oxidation of cyclooctene

[0026] (1) Preparation of tetraethylammonium perrhenate

[0027] Tetraethylammonium bromide and KOH were mixed and dissolved in a certain amount of absolute ethanol solution at a molar ratio of 1:1.1, stirred and reacted at room temperature for 12 hours, white potassium bromide was precipitated, and the potassium bromide precipitate was removed by filtration to obtain Ethanol solution of tetraethyl quaternary ammonium base. In the obtained ethanol solution of tetraethylquaternary ammonium base, NH was added in a molar ratio of 1:1.1 4 ReO 4 , heated to 80°C, ammonia gas is released, heated to reflux until no ammonia gas is released, then lowered to room temperature, stirred for 24 hours, filtered to remove excess ammonium perrhenate, and the filtrate was concentrated by rotary evaporator to obtain crystals, pumped Filter and dry in vacuum at 40°C for 6 hours to obtain pure tetraethylamm...

Embodiment 3

[0032] Embodiment 3: the method for preparing suberic acid by oxidation of cyclooctene

[0033] (1) Preparation of tetrabutylammonium perrhenate

[0034] Tetrabutylammonium bromide and KOH were mixed and dissolved in a certain amount of absolute ethanol solution at a molar ratio of 1:1.1, stirred and reacted at room temperature for 12 hours, and white potassium bromide was precipitated, and the potassium bromide precipitate was removed by filtration to obtain Ethanol solution of tetrabutyl quaternary ammonium base. In the obtained ethanol solution of tetrabutyl quaternary ammonium base, NH was added in a molar ratio of 1:1.1 4 ReO 4 , heated to 80°C, ammonia gas is released, heated to reflux until no ammonia gas is released, then lowered to room temperature, stirred for 24 hours, filtered to remove excess ammonium perrhenate, and the filtrate was concentrated by rotary evaporator to obtain crystals, pumped Filter and dry in vacuum at 40°C for 6 hours to obtain pure tetrabut...

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Abstract

The invention relates to a method for preparing suberic acid through cyclooctene oxidation. According to the technical scheme, the method comprises the following steps: mixing tetra-allkylammonium perrhenate and alkyl-imidazolim disulfate ionic liquid in a certain proportion so as to form a composite phase transfer catalyst, and meanwhile, carrying out catalytic oxidation reaction on cyclooctene in the presence of alkyl-imidazolim disulfate ionic liquid serving as a reaction solvent and a hydrogen peroxide solution serving as an oxidizing agent, wherein the reaction temperature is 40-70 DEG C, the pressure is normal pressure, and the reaction time is 0.5-4 hours. After reaction, the gas chromatography detection shows that the conversion rate of the cyclooctene is above 90% and the cyclooctene yield is above 60%. The method has relatively high selectivity, effectively improves the selectivity of reaction and achieves a satisfactory effect.

Description

technical field [0001] The invention relates to the field of chemical catalysis, in particular to a method for preparing suberic acid, an important chemical product, by catalyzing the oxidation of cyclooctene. Background technique [0002] Suberic acid is an important chemical that is widely found in the trunks of cork trees in nature. Suberic acid can undergo reactions such as esterification, acyl halide, amidation and reduction, and undergo thermal decomposition reactions when heated. Its main use is to react with diols and diamines to produce polyesters and polyamides, and it is also used in organic synthesis. Industrially, it is obtained by oxidation of castor oil or ricinoleic acid or cyclooctane, usually catalyzed by 50% sulfuric acid. Suberic acid can also be obtained by oxidation of cyclooctene. The main possible products of the oxidation of cyclooctene to suberic acid are as follows: [0003] [0004] Among them, after cyclooctene is oxidized, its epoxide (3)...

Claims

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Application Information

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IPC IPC(8): C07C55/02C07C51/31
CPCC07C51/31C07C55/02Y02P20/54
Inventor 臧树良周明东孟文叶李蕊王景芸
Owner LIAONING UNIVERSITY OF PETROLEUM AND CHEMICAL TECHNOLOGY