Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

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
View PDF2 Cites 10 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 conducive to environmental protection
In 1989, Xiong Yutang, Department of Chemistry, Shanxi University et al [Shanxi Chemical Industry, 2, 17, 1989] and Gao Weimin, Anshan Iron and Steel Institute et al in 1999 [Fuel and Chemical Industry, 30 (2), 66, 1999] reported the use of dimethyl sulfoxide ( DMSO) as solvent, potassium hydroxide as catalyst, 56 ℃ of reaction temperature, air oxidation fluorene to prepare 9-fluorenone, productive rate is all lower than 93%, the product purity 99% by recrystallization, the method used dimethyl methylene Sulfone has a high boiling point. After the reaction, a large amount of water is added to precipitate the product, and it will be difficult to treat DMSO-containing wastewater 10 times larger than the solvent; the reaction process needs to be strictly controlled. and benzene) have adverse effects on cost and environmental protection

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

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%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C49/675C07C49/697C07C45/36
Inventor 张昭张鑫李鹏飞王振李奋强
Owner SHANXI UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com