Method for preparing 9-fluorenone through fluorene

A technology of fluorenone and reaction, applied in the field of organic synthesis, can solve the problems of undisclosed types of quaternary ammonium salt, large solvent loss, high reaction temperature, etc., and achieve the effect of simplifying the synthesis process of fluorenone and simplifying the refining method

Active Publication Date: 2014-05-14
BAOSHUN TECH CO LTD +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This study does not add water, quaternary ammonium salts are difficult to play the role of phase transfer catalysts, and the reaction temperature is high, above 90 ° C, the loss of solvent is large; the document does not disclose the types of quaternary ammonium salts and other issues

Method used

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  • Method for preparing 9-fluorenone through fluorene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] In a 250mL three-necked flask, sequentially add 60.42g of industrial fluorene, 62.87g of 9-fluorenone, 1.00g of tetrabutylammonium chloride, 6g of NaOH and 9mL of water, heat the three-necked flask in a water bath at 80°C, and control the mechanical stirring rate to 300r / min. 300×2mL / min air was bubbled through 80°C water and then entered into the reaction flask to start the reaction. During the reaction, the conversion of fluorene was monitored by thin-layer chromatography. After 10.5 hours of reaction, the raw material point disappeared, and the reaction was continued for half an hour to stop the reaction. The reaction liquid was transferred to warm water to cool while it was hot, stirred thoroughly, cooled, and filtered to obtain a yellow solid, which was dried naturally in air to obtain 124.46 g of 9-fluorenone. Chromatographic analysis showed that the content of 9-fluorenone was 97.01%, and the raw material fluorene was completely converted.

Embodiment 2

[0047] In a 250 mL three-necked flask, 61.86 g of industrial fluorene, 30 g of 9-fluorenone, and 1.20 g of tetrabutylammonium bromide were sequentially added, and the others were the same as in Example 1. After 8 hours of reaction, the raw material point disappeared, and the reaction was continued for half an hour to stop the reaction. A crude product of 92.86 g was obtained. Chromatographic analysis showed that the content of 9-fluorenone was 96.87%, and the raw material fluorene was completely converted.

Embodiment 3

[0049] In a 250 mL three-necked flask, 61.45 g of industrial fluorene, 45.44 g of 9-fluorenone, and 1.20 g of tetrabutylammonium hydrogen sulfate were successively added, and the others were the same as in Example 1. After 7.5 hours of reaction, the raw material point disappeared, and the reaction was continued for half an hour to stop the reaction, and 113.19 g of yellow crystals were obtained. Chromatographic analysis showed that the content of 9-fluorenone was 96.51%, and the raw material fluorene was completely converted.

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Abstract

Provided is a method for preparing 9-fluorenone through fluorine. The industrial fluorine is adopted as raw materials, the 9-fluorenone and water are adopted as solvents, alkali is adopted as catalysts, quaternary ammonium salt is adopted as phase transfer agents, oxygen-containing gas is piped in as oxidizing agents, the 9-fluorenone is synthetised at the reaction temperature of 70 DEG C to 83 DEG C, and the raw materials of the fluorine are added at one time or constantly replenished along with the reaction. The products, 9-fluorenone, are adopted as solvents, the process of solvent fluorenone separation, recycling and the like is eliminated, reaction liquid separation and 9-fluorenone purification are operated in a coupling mode, and the 9-fluorenone synthetic process is greatly simplified. The alkali, the quaternary ammonium salt and the by-product, water, are all recycled. Through the fluorine replenishing feeding mode, the utilization efficiency of a reactor is improved.

Description

technical field [0001] The invention provides a method for converting fluorene into 9-fluorenone by using a product 9-fluorenone and water as a solvent through a phase transfer catalytic oxidation reaction. The invention belongs to the field of organic synthesis. Background technique [0002] Coal tar and related industries have developed rapidly in recent years. Fluorene is one of the important components of coal tar, accounting for 1-2% of the mass of coal tar, and the yield of fluorene separated from coal tar is large. The use of fluorene is limited, and its derivatives are of high value. Therefore, it is imperative to develop high value-added downstream products of fluorene from tar fluorene as the starting material. Fluorenone is a good deep-processing product of tar fluorene and an important chemical raw material. Most fluorene derivatives are synthesized via fluorenone. Therefore, fluorenone has a large demand in the market, and its related industries have broad ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/675C07C45/36
CPCC07C45/36C07C2603/18
Inventor 高占先于丽梅闫俊李汇丰何永超史正茂
Owner BAOSHUN TECH CO LTD
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