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Method for preparing 9-fluorenone by liquid-phase oxidation

A liquid-phase oxidation method and fluorenone technology, which are applied in the preparation of carbon-based compounds, chemical instruments and methods, and the preparation of organic compounds, can solve the problems of low yield and high product cost, achieve less solvent consumption, and reduce production The effect of high efficiency and productivity

Inactive Publication Date: 2014-09-10
SHENYANG RES INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In order to overcome the shortcomings of high product cost and low yield in the existing preparation methods, the invention provides a method for preparing 9-fluorenone by liquid phase oxidation

Method used

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  • Method for preparing 9-fluorenone by liquid-phase oxidation
  • Method for preparing 9-fluorenone by liquid-phase oxidation
  • Method for preparing 9-fluorenone by liquid-phase oxidation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: Preparation of 9-fluorenone by oxidation of fluorene

[0021] According to the following reaction formula,

[0022]

[0023] Operation steps: Add 20 grams of fluorene (0.12mol), 40 grams of N,N-dimethylformamide, 0.2 grams of potassium hydroxide (0.0036mol) in a 100 milliliter three-necked flask equipped with a reflux condenser and mechanical stirring, Start stirring, air oxidation, react at 30°C for 0.5 hours, and track through gas chromatography analysis. When the content of raw material fluorene is less than 0.1%, stop the air, and the reaction ends; the reaction liquid is filtered after distillation, washed with water, and dried to obtain a yellow solid 9- Fluorenone 21.5g, purity 99.5%, yield 99%. After the reaction, the used solvent is retained, and the next batch continues to be recycled.

Embodiment 2

[0024] Embodiment 2: Preparation of 9-fluorenone by oxidation of fluorene (solvent application)

[0025] According to the following reaction formula,

[0026] Operation steps: Add 20 grams of fluorene (0.12mol), 40 grams of N,N-dimethylformamide recovered in Example 1 above, and 0.2 grams of hydrogen peroxide into a 100 milliliter three-necked flask equipped with a reflux condenser and mechanical stirring Potassium (0.0036mol), start stirring, air oxidation, react at 30°C for 0.5 hours, track through gas chromatography analysis, when the content of raw material fluorene is less than 0.1%, stop the air flow, and the reaction ends; the reaction liquid is filtered after distillation, washed with water, and dried , to obtain 21.5 g of yellow solid 9-fluorenone with a purity of 99.5% and a yield of 99%. After the reaction, the used solvent continues to be retained, and the next batch continues to be recycled.

Embodiment 3

[0027] Example 3: Preparation of 9-fluorenone by oxidation of fluorene

[0028] Operation steps: add 20 grams of fluorene (0.12mol), 40 grams of N,N-dimethylformamide, 0.07 grams of potassium hydroxide (0.0012mol) in a 100 milliliter three-necked flask equipped with a reflux condenser and mechanical stirring, Turn on stirring, air oxidation, and react at 30°C for 3 hours. After distillation, the reaction solution was filtered, washed with water and dried to obtain 21.5 g of yellow solid 9-fluorenone with a purity of 99.5% and a yield of 99%.

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Abstract

The invention belongs to the field of fine chemicals and in particular relates to a method for preparing 9-fluorenone by liquid-phase oxidation. The method comprises the steps of dissolving fluorene in N, N-dimethyl formamide, and then adding a catalyst, stirring at 30-40 DEG C and under atmospheric pressure, carrying out air oxidation, reacting for 0.5-3 hours, distilling, filtering, washing with water and drying to obtain 9-fluorenone of which the yield is 98% and the purity is 99-99.5%, wherein the feed weight ratio of fluorene to N, N-dimethylformamide is 1 to (2-5), and the feed molar ratio of fluorene to potassium hydroxide is 1 to (0.01-0.05). The solvent used in the method disclosed by the invention can be recycled without further processing. The method disclosed by the invention has the advantages of mild reaction conditions, simple operation, relatively small amount of solvent, high yield, low cost, low environmental pollution and relatively short reaction time, the solvent needs not to be further processed and can be recycled after being used and the method is suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the field of fine chemicals, and in particular relates to a method for preparing 9-fluorenone by a liquid-phase oxidation method. Background technique [0002] 9-Fluorenone is an important fine organic chemical raw material. This compound is not only an important raw material for preparing photoconductive materials, but also a photopolymerization initiator for various compounds, such as acrylonitrile. As a pharmaceutical intermediate, 9-fluorenone can be used to synthesize a variety of drugs, mainly including sympathetic nerve inhibitors, antispasmodics, anti-cancer and anti-tuberculosis drugs, etc. In addition, many drugs using 9-fluorenone as raw materials are under development. 9-fluorenone can also be made into insecticides, high-efficiency herbicides and plant growth aids. 9-fluorenone can also be used as a dye intermediate, which can be used in the production of detergents, liquid glitter, etc. [0003] The liquid-phase...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/675C07C45/36
CPCC07C45/36C07C2603/18C07C49/675
Inventor 尹荃闫海生喻滔任树杰李丽刘冰
Owner SHENYANG RES INST OF CHEM IND