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Preparation method of 4-bromo-5-nitro-1,8-naphthalic anhydride

A technology of nitro and naphthalene anhydride, applied in the field of preparation of 4-bromo-5-nitro-1,8-naphthalene anhydride, which can solve the problems of difficulty in industrialization and application, narrow substrate universality, etc., and achieve cheap raw materials , Reduce production cost, good effect of atomic economy

Active Publication Date: 2020-07-03
YANGTZE UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are still some defects in these processes, such as the difficulty of industrialization and application, the narrow universality of the substrate, and the harmonious relationship between product function, cost and environmental protection.

Method used

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  • Preparation method of 4-bromo-5-nitro-1,8-naphthalic anhydride
  • Preparation method of 4-bromo-5-nitro-1,8-naphthalic anhydride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022]

[0023] Add 15.4g (0.0998mol) acenaphthene, 10.29g (0.1mol) sodium bromide, 2.3759 g (0.01mol) NiCl to the round bottom flask 2 ·6H 2 O (catalyst), 198mL glacial acetic acid and 99mL water, then dropwise added 204mL hydrogen peroxide and reacted at 20°C for 3 hours, then cooled the reaction solution to room temperature, suction filtered, and washed with 5-10mL H 2 The filter cake was washed with O and absolute ethanol, and the yellow product 5-bromoacenaphthene was obtained after vacuum drying with a yield of 92.4%. HRMS(ES+)C 12 h 10 Br([M+H]) + The theoretical value is 232.9966, and the measured value is 232.9964. As determined by HPLC, the purity of the target compound was 98.5%.

Embodiment 2

[0025] Except that catalyst is 1.7048g (0.01mol) CuCl in embodiment 2 2 2H 2 O, except that the temperature was controlled at 15° C. for 4 hours, other conditions and preparation steps were the same as in Example 1 to obtain a yellow product, 5-bromoacenaphthene, with a yield of 94.4%. HRMS(ES+)C 12 h 10 Br([M+H]) + The theoretical value is 232.9966, and the measured value is 232.9960. As determined by HPLC, the purity of the target compound was 98.3%.

Embodiment 3

[0027] Except that catalyst is 3.7258g (0.01mol) CeCl in embodiment 3 3 ·7H 2 O, except that the temperature was controlled at 20° C. for 3 hours, other conditions and preparation steps were the same as in Example 1 to obtain a yellow product, 5-bromoacenaphthene, with a yield of 97.5%. HRMS(ES+)C 12 h 10 Br([M+H])+ theoretical value 232.9966, measured value 232.9963. As determined by HPLC, the purity of the target compound was 99.1%.

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Abstract

The invention belongs to the technical field of fine chemical engineering, and particularly relates to a preparation method of 4-bromo-5-nitro-1,8-naphthalic anhydride. The preparation method taking acenaphthene as a raw material comprises the following steps: adding acenaphthene, sodium bromide and a catalyst into a mixed solution of glacial acetic acid and water, dropwise adding hydrogen peroxide, and carrying out a temperature-controlled reaction to obtain 5-bromoacenaphthene; adding 5-bromoacenaphthene and metal nitrate into glacial acetic acid, and carrying out temperature-controlled stirring reaction to obtain 4-bromo-5-nitroacenaphthene; and adding 4-bromo-5-nitroacenaphthene and a catalyst into glacial acetic acid, introducing oxygen, and heating to react in order to obtain 4-bromine-5-nitro-1,8-naphthalic anhydride. The method for preparing the target product has the advantages of cheap and accessible raw materials, low preparation cost, high product yield, mild conditions inthe preparation process and favorable atom economy, and can implement industrial batch production.

Description

technical field [0001] The invention belongs to the field of fine chemicals, and in particular relates to a preparation method of 4-bromo-5-nitro-1,8-naphthalene anhydride. Background technique [0002] 4-Bromo-5-nitro-1,8-naphthalene anhydride is an important fine chemical and an important intermediate in the dye and pigment industry. The current industrial preparation methods still use traditional methods such as N-bromosuccinimide (NBS) / dimethylformamide (DMF) bromination, mixed acid (sulfuric acid / nitric acid) nitration and sodium dichromate oxidation. This process obviously has defects such as serious environmental pollution (many wastes, high corrosion) and high cost. Therefore, it is urgent to develop a new, green and economical synthesis process. [0003] Today's green bromination, nitrification, and oxidation technologies have attracted widespread attention due to their high efficiency, high selectivity, and atom economy. In the reported green bromination technolo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/80
CPCC07D311/80Y02P20/584
Inventor 吴爱斌胡艳雄周五师春甜
Owner YANGTZE UNIVERSITY
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