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A kind of method that liquid phase oxidation method prepares 2-bromofluorenone

A liquid-phase oxidation method and bromofluorenone technology, applied in the field of fine chemicals, can solve the problems of high product cost and low yield, and achieve the effects of reducing production efficiency, less solvent consumption, and reducing recovery losses

Active Publication Date: 2016-08-31
SHENYANG RES INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] 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 2-bromofluorenone by liquid phase oxidation

Method used

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  • A kind of method that liquid phase oxidation method prepares 2-bromofluorenone
  • A kind of method that liquid phase oxidation method prepares 2-bromofluorenone
  • A kind of method that liquid phase oxidation method prepares 2-bromofluorenone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Example 1: Preparation of 2-bromo-9-fluorenone by oxidation of 2-bromofluorene

[0016] Follow the reaction below,

[0017]

[0018] Operation steps: Add 20 grams of 2-bromofluorene (0.082mol), 80 grams of N,N-dimethylformamide, 1 gram of potassium hydroxide (0.018 mo1), start stirring, react for 2 hours at 35°C, and track through gas chromatography analysis. When the content of raw material fluorene is less than 0.1%, stop ventilating the air and the reaction ends; the reaction solution is filtered after distillation, washed with water, and dried to obtain a purity of 99.5%. % of 2-bromo-9-fluorenone, yield 96%. After the reaction, the used solvent is retained, and the next batch continues to be recycled.

Embodiment 2

[0020] Operation steps: Add 20 grams of 2-bromofluorene (0.082mol), 80 grams of N,N-dimethylformamide (recovered in Experiment 1), and 1 g Potassium hydroxide (0.018mol), start stirring, react at 35°C for 2 hours, track through gas chromatography analysis, when the content of raw material fluorene is less than 0.1%, stop ventilating the air, and the reaction ends; the reaction solution is filtered after distillation, washed with water, and dried. That is, 2-bromo-9-fluorenone with a purity of 99.5% was obtained with a yield of 96%. After the reaction, the used solvent is retained, and the next batch continues to be recycled.

Embodiment 3

[0021] Example 3, Preparation of 2-bromo-9-fluorenone by oxidation of 2-bromofluorene

[0022] Operation steps: Add 20 grams of 2-bromofluorene (0.082mol), 70 grams of N,N-dimethylformamide, 1 gram of sodium hydroxide (0.025 mol), start stirring, and react at room temperature for 3 hours. The reaction solution was filtered after distillation, washed with water, and dried to obtain 2-bromo-9-fluorenone with a purity of 99.4% and a yield of 95.5%.

[0023] Example, Preparation of 2-bromo-9-fluorenone by oxidation of 4,2-bromofluorene

[0024] Operation steps: Add 20 grams of 2-bromofluorene (0.082mol), 90 grams of N,N-dimethylformamide, 1 gram of sodium methylate (0.02mol ), start stirring, and react at 40° C. for 4 hours. The reaction solution was filtered after distillation, washed with water, and dried to obtain 2-bromo-9-fluorenone with a purity of 99.4% and a yield of 95%.

[0025] The physical constants and spectrum data of 2-bromo-9-fluorenone prepared by oxidation of...

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Abstract

The invention belongs to the field of fine chemical engineering, and particularly relates to a method for preparing 2-bromofluorenone by liquid-phase oxidation. The method comprises the following steps: dissolving 2-bromofluorene in N,N-dimethylformamide, adding a catalyst, stirring at 30-40 DEG C under normal pressure, carrying out air oxidation, reacting for 2-4 hours, distilling, filtering, washing with water, and drying to obtain the 2-bromofluorenone. The yield is 96%, and the purity is 99-99.5%. The weight ratio of the 2-bromofluorene to the N,N-dimethylformamide is 1:(3.5-5); and the mole ratio of the 2-bromofluorene to the catalyst is 1:(0.03-0.5). The method has the advantages of mild reaction conditions, lower solvent consumption, high yield, low cost, small environmental pollution, recyclable solvent without further treatment after use and short reaction time, is simple to operate, and is very 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 2-bromofluorenone by a liquid-phase oxidation method. Background technique [0002] 2-Bromofluorenone is an important fine organic chemical raw material. This compound is not only an important raw material for preparing photoconductive materials, but also another important application field for silver-based photosensitive materials. [0003] The method disclosed in the prior art to prepare 2-bromofluorenone with 2-bromofluorene as a raw material is a liquid phase air oxidation method. In the current liquid phase preparation method for 2-bromofluorenone, the solvent selected is dimethyl sulfoxide and Tetrahydrofuran and dimethyl sulfoxide have a high boiling point, and the recovery process requires distillation under reduced pressure. When the heating temperature of dimethyl sulfoxide is higher than 90 ° C, it will decompose, and the reaction needs ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/697C07C45/36
CPCC07C45/36C07C2603/18C07C49/697
Inventor 尹荃闫海生喻滔任树杰李丽陈二中
Owner SHENYANG RES INST OF CHEM IND
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