Preparation method of 2-bromofluorenone

A technology of bromofluorenone and fluorenone, which is applied in the field of preparation of 2-bromofluorenone, can solve problems such as environmental pollution, high toxicity, and difficulty in removal, so as to improve economic environmental protection, high active bromine content, and improve product purity Effect

Inactive Publication Date: 2019-10-22
郑州圣壹新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The bromination method uses 9-fluorenone and brominating reagents as raw materials to synthesize 2-bromofluorenone, and some use liquid bromine as the brominating reagent, which is not conducive to safe production because of its volatile and highly toxic characteristics, and subsequent purification The process cannot efficiently remove the by-product 2,7-dibromofluorenone, and cannot obtain high-purity 2-bromofluorenone products
The oxidation method is to prepare 2-bromofluorenone through the oxidation of 2-bromofluorene in the liquid phase, and some use organic solvents such as pyridine, tetrahydrofuran and N,N-dimethylformamide as the reaction medium, and organic solvents can cause severe Environmental pollution; some use the water phase as the reaction medium, and the moisture content of the target product increases during the oxidation process, and it is difficult to remove it in the later stage of purification, so high-quality 2-bromofluorenone products cannot be obtained

Method used

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Examples

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preparation example Construction

[0027] A preparation method of 2-bromofluorenone, comprising the following steps:

[0028] (1) Mix 9-fluorenone, catalyst and water and heat to 40-60°C, add dibromohydantoin in batches for reaction, the weight ratio of 9-fluorenone and dibromohydantoin is 1:(1.5 ~2);

[0029] (2) Cool down to room temperature after the reaction, centrifuge, remove bromine and wash to obtain crude 2-bromofluorenone;

[0030] (3) The crude 2-bromofluorenone is mixed with a crystallization solvent and heated to 65-75° C., fully dissolved and cooled down to room temperature, and centrifuged and sprayed to remove impurities to obtain 2-bromofluorenone.

[0031] In some embodiments of the present invention, the weight ratio of 9-fluorenone, catalyst and water in step (1) is 1:0.01-0.1:3-8.

[0032] In some embodiments of the present invention, the dibromohydantoin in step (1) is added in 3-5 times in equal amounts, and the time interval between each addition is 0.5-1.5h; the reaction time is 16-24...

Embodiment 1

[0046] The industrial preparation method of environment-friendly 2-bromofluorenone comprises the following steps:

[0047] 1) Add 1400L of water, 14kg of catalyst tetrabutylammonium bromide, and 180kg of 9-fluorenone into a 3000L enamel kettle equipped with a vent recovery device and mechanical stirring, and mix well. Heat to 45°C while stirring, then add 285kg of dibromohydantoin in five batches, each batch is equally divided into 57kg, and add a batch every 1h. After all the dibromohydantoin was added within 5 hours, the reaction was continued for 18 hours in the temperature range of 45-55°C.

[0048] 2) Cool down to room temperature after the reaction, centrifuge and wash with 8wt% NAOH solution to obtain crude 2-bromofluorenone. The purity of the crude product by liquid chromatography was 98.3%. Collect the reaction mother liquor for recycling.

[0049] 3) Mix the crude product of 2-bromofluorenone and absolute ethanol solvent in the crystallization tank at a weight rat...

Embodiment 2

[0052] The industrial preparation method of environment-friendly 2-bromofluorenone comprises the following steps:

[0053]1) In a 2000L enamel kettle equipped with a vent recovery device and a mechanical agitator, add 750L of reaction mother liquor, 200L of water, 2kg of catalyst tetrabutylammonium bromide, and 120kg of 9-fluorenone and mix well. Heat to 45°C while stirring, then add 190kg of dibromohydantoin in four batches, each batch is equally divided into 47.5 kg, and a batch is added every 1.2h. After all the dibromohydantoin was added within 5 hours, the reaction was continued for 16 hours at a temperature range of 45-55°C.

[0054] 2) Cool down to room temperature after the reaction, centrifuge and wash with 8wt% NAOH solution to obtain crude 2-bromofluorenone. The purity of the crude product by liquid chromatography was 98.5%. Collect the reaction mother liquor for recycling.

[0055] 3) The crude product of 2-bromofluorenone and absolute ethanol solvent are mixed ...

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Abstract

The invention belongs to the technical field of fine chemical industry, and discloses a preparation method of 2-bromofluorenone, the preparation method comprises the following steps: (1) mixing 9-fluorenone, a catalyst and water, heating to 40-60 DEG C, and adding dibromohydantoin in batches for reaction, wherein the weight ratio of 9-fluorenone to dibromohydantoin is 1: (1.5-2); (2) cooling to room temperature after the reaction, centrifuging, removing bromine and washing to obtain a 2-bromofluorenone crude product; (3) mixing the 2-bromofluorenone crude product with a crystallization solvent, heating to 65-75 DEG C, fully dissolving, cooling to room temperature, centrifuging, spraying and removing impurities to obtain the 2-bromofluorenone. The preparation method is economical, safe, environment-friendly and efficient, and is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of fine chemicals, in particular to a preparation method of 2-bromofluorenone. Background technique [0002] The description of the background technology of the present invention belongs to the relevant technology related to the present invention, and is only used to illustrate and facilitate the understanding of the content of the present invention. prior art on the filing date. [0003] In recent years, fluorenone and its derivatives have become an important class of functional compounds, 2-bromofluorenone is one of the important ones, used to prepare functional polymer materials, medicine, pesticides, photosensitive dyes, especially in organic electronics The field of luminescent materials has broad application prospects. [0004] At present, there are mainly two types of preparation methods of 2-bromofluorenone reported at home and abroad, namely bromination method and oxidation method. The brominatio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/63C07C49/697
CPCC07C45/63C07C2603/18C07C49/697
Inventor 佘永康
Owner 郑州圣壹新材料科技有限公司
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