Oxidation preparation method for 9- fluorenone compound from fluorine compound

A technology of fluorene compounds and compounds, which is applied in the field of oxidative preparation of 9-fluorenone compounds by oxidizing fluorene compounds, can solve the problems of complex operation, difficulty, and high cost, and achieve the effects of mild reaction conditions, less environmental pollution, and easy operation

Inactive Publication Date: 2007-05-16
SHANXI UNIV
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Problems solved by technology

Relevant reports at home and abroad are prepared by the oxidation of fluorene compounds. The method for preparing 9-fluorenone compounds mainly includes the following aspects: In 1996, Nippon Shokubai Co., Ltd. used a catalyst containing metal vanadium, titanium and alkali metals to prepare 9-fluorene by a gas phase method. Ketones, the reaction temperature is above 400°C, and the yield is less than 95% [ZL.96123084.3]
In 2003, Anshan Iron and Steel Group Corporation used a compound containing vanadium and compounds containing potassium, tin or titanium as a catalyst to prepare 9-fluorenone [ZL.99112742.0] by gas-phase oxidation of fluorene at 300-450°C. A method for preparing 9-fluorenone by gas-phase oxidation of fluorene, complicated operation and high cost
This method uses CrO 3 As an oxidant, not only the cost of the product is high, but also not conduc...

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 11

[0014] Example 1.1 Oxidation of fluorene to prepare 9-fluorenone

[0015] Operation steps: Add 20 g of fluorene (0.12 mol), 120 ml of tetrahydrofuran, and 6.70 g of potassium hydroxide (0.12 mol) into a 250 ml three-necked flask equipped with a reflux condenser and mechanical stirring, start stirring, and react at room temperature for 6 hours. The reaction solution was filtered to remove potassium hydroxide, the filtrate was distilled to remove the solvent, washed three times with water, and dried to obtain 9-fluorenone with a purity of 99.0% and a yield of 98.5%.

Embodiment 12

[0016] Example 1.2 Oxidation of fluorene to prepare 9-fluorenone

[0017] Operation steps: add 20g fluorene (0.12mol) in 250 milliliters of three-neck flasks that reflux condenser and mechanical stirring are housed, 100 milliliters of tetrahydrofuran (the solvent that reclaims after last example uses), 16.87g Potassium Hydroxide (0.3mol), Start stirring, and react at room temperature for 5 hours. The reaction solution was filtered to remove insoluble matter, the filtrate was distilled to remove the solvent, washed with water three times, and dried to obtain 9-fluorenone with a purity of 99.2% and a yield of 99.1%.

[0018] Physical constants and spectral data of 9-fluorenone:

[0019] Appearance of the product: yellow solid; melting point: 83-85°C; IR(KBr)cm -1 : 3060,3050,1710,1602,1563,1433,1365,1324,1152,1099,1003,876,854,671,661; H 1 NMR δppm: 7.65 (d, 2H), 7.45-7.48 (m, 4H), 7.28 (d, 2H).

Embodiment 21

[0020] Example 2.1 Preparation of 2,7-dibromo-9-fluorenone by oxidation of 2,7-dibromofluorene

[0021] Operation steps: Add 20g 2,7-dibromofluorene (0.06mol), 120ml tetrahydrofuran, 1.68g potassium hydroxide (0.03mol) to a 250ml three-necked flask equipped with a reflux condenser and mechanical stirring, start stirring, and The reaction was carried out for 2.5 hours. The reaction solution was suction-filtered to remove insoluble matter, the filtrate was distilled to remove the solvent, washed with water three times, and dried to obtain 2,7-dibromo-9-fluorenone with a purity of 99.5%, and a yield of 99.0%.

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Abstract

The invention discloses a preparing method of 9-fluorenone compound through oxidizing fluorene compound, which comprises the following steps: dissolving fluorene compound in the tetrahydrofuran; adding potassium hydroxide; setting the weight rate of fluorene compound and tetrahydrofuran at 1:4-6 with the molar rate of fluorene compound and potassium hydroxide at 1:0.5-2.5; stirring under normal temperature and pressure; oxidizing in the air; reacting for 1-8h; filtering; distilling; washing; drying; obtaining the product with producing rate at 98-99% and purity at 99-99.5%.

Description

technical field [0001] The invention relates to aromatic compounds, in particular to a method for preparing 9-fluorenone compounds by oxidation of fluorenone compounds. Background technique [0002] 9-fluorenone compounds are important intermediate raw materials for the synthesis of fine chemicals, and are widely used in the synthesis and preparation of dyes, photoconductive materials, medicine and luminescent materials. Relevant reports at home and abroad are prepared by the oxidation of fluorene compounds. The method for preparing 9-fluorenone compounds mainly includes the following aspects: In 1996, Nippon Shokubai Co., Ltd. used a catalyst containing metal vanadium, titanium and alkali metals to prepare 9-fluorene by a gas phase method. Ketones, the reaction temperature is above 400°C, and the yield is less than 95% [ZL.96123084.3]. In 2003, Anshan Iron and Steel Group Corporation used a compound containing vanadium and compounds containing potassium, tin or titanium as...

Claims

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Application Information

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IPC IPC(8): C07C49/675C07C49/697C07C45/36
Inventor 张昭张鑫李鹏飞王振李奋强
Owner SHANXI UNIV
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