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Method for preparing 9-fluorenone through using industrial fluorene

A fluorenone and industrial technology, applied in the field of organic synthesis, can solve the problems of high reaction temperature, undisclosed type of quaternary ammonium salt, difficult phase transfer catalyst effect of quaternary ammonium salt, etc., and achieve the effect of low energy consumption

Active Publication Date: 2013-12-25
BAOSHUN TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This research does not add water phase, quaternary ammonium salt is difficult to play the role of phase transfer catalyst, and the reaction temperature is high, above 90 ℃, the loss of solvent is large; the document does not disclose the type of quaternary ammonium salt and other issues

Method used

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  • Method for preparing 9-fluorenone through using industrial fluorene

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] ① Take 5.0g of industrial fluorene, 0.16g of reagent grade tetra-n-butylammonium chloride and 15mL of toluene, put them in a 50mL three-necked round-bottomed flask, and mechanically stir in a constant temperature water bath at 50°C until completely dissolved to obtain an oil phase;

[0049] ②Dissolve sodium hydroxide in water to prepare 10g of 30wt% aqueous phase;

[0050] ③Mix the oil phase and the water phase, mechanically stir in a constant temperature water bath at 50°C at a stirring speed of 300r / min, feed air at a speed of 200mL / min, monitor the reaction process with thin-layer chromatography, after 1.6h, thin-layer The chromatogram showed that the fluorene spot of the raw material disappeared completely, and the reaction was stopped after continuing the reaction for 0.5h to obtain the reaction solution;

[0051] ④ cooling the reaction solution, separating the water layer, reclaiming the alkali solution, taking the oil layer, washing the oil layer with water, dilu...

Embodiment 2

[0054] Except that steps 1. and 3. were changed to stirring, dissolving and reacting at 40° C., the others were the same as in Example 1. After 3.5 hours of reaction, thin-layer chromatography showed that the raw material fluorene spots completely disappeared, and the reaction was continued for 0.5 hours to stop the reaction. Obtain 4.9g product after a series of treatment of embodiment 1 step ④.

[0055] The above product was sampled for GC analysis, and the spectrum showed that there was no fluorenone component. Except for the impurities brought in by 9-fluorenone and raw material industrial fluorene, no new components appeared; after recrystallization of crude fluorenone with 5ml ethanol , sampling for GC analysis, the spectrogram shows that the content of 9-fluorenone is 100%.

Embodiment 3

[0057] Except that 0.1g of tetra-n-butylammonium chloride is replaced with 0.16 of tetra-n-butylammonium chloride in step 1., other is the same as embodiment 1. After 2.5 hours of reaction, TLC showed that the raw material fluorene spots completely disappeared, and the reaction was continued for 0.5 hours to stop the reaction.

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Abstract

A method for preparing 9-fluorenone through using industrial fluorene is characterized in that a raw material industrial fluorene (having a purity of above 95%) reacts with an oxygen-containing gas at a low temperature under stirring in a solvent comprising toluene and water under the action of an alkali as a catalyst and a quaternary ammonium salt as a phase transfer agent to form 9-fluorenone. The fluorene conversion rate can reach 100% under appropriate reaction conditions. The alkali and solvent recovered in the invention can be recycled without special complex treatment processes, so it is beneficial for industrialization; and in the invention, the recycle of the catalyst alkali, the phase transfer agent quaternary ammonium salt and the solvent, a recrystallization technology and the like are researched, pure fluorenone is obtained, and the complete preparation method of the 9-fluorenone is provided.

Description

technical field [0001] The invention provides a method for converting industrial fluorene into 9-fluorenone by using toluene and water as solvents 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 output of fluorene separated from coal tar is large. The use of fluorene is limited, and its derivatives are of high value. The price of fluorene itself is relatively low. With the intensification of market competition among enterprises, merchants have higher and higher requirements for the purity of fluorene. The fluorene separated from the washing oil can no longer meet the requirements. If it continues to be purified, the production cost will be too high , seriously affecting the development of enterprises...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/675C07C45/36C07C45/78
CPCY02P20/584
Inventor 高占先于丽梅郑道源李汇丰何永超
Owner BAOSHUN TECH CO LTD
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