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Preparation method of 1,8-disubstituted naphthalene mononitration derivative

A disubstituted and derivative technology, applied in the field of preparation of 1,8-disubstituted naphthalene mononitrated derivatives, can solve the problems of difficult application, low substrate universality, environmental pollution, etc., and achieve high product yield , low cost, high purity effect

Active Publication Date: 2019-07-23
YANGTZE UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the industry still follows the traditional method of nitrification by mixed acid (sulfuric acid / nitric acid) more than one hundred years ago, but this process has defects such as no nitrification selectivity and serious environmental pollution. Today's clean and green nitrification technology is due to its high efficiency, high Selectivity and atom economy and other characteristics have attracted extensive attention
[0003] Among the reported green nitrification technologies, such as solid acid catalysis and Lewis acid catalysis, some achievements have been made in replacing sulfuric acid to reduce corrosion and waste discharge, catalyst recovery and recycling, but there are still some defects in these processes. , such as the difficulty of industrialization and application, the low universality of substrates, and how to solve the relationship between function, cost and greenness, etc.

Method used

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  • Preparation method of 1,8-disubstituted naphthalene mononitration derivative
  • Preparation method of 1,8-disubstituted naphthalene mononitration derivative
  • Preparation method of 1,8-disubstituted naphthalene mononitration derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0027]

[0028] 3.12g (20mmol, M=156.23) 1,8-dimethylnaphthalene (I-1), 9.00g (24 mmol, M=375.13) Al(NO 3 ) 3 .9H 2 O was added to 30 mL CH 3 In COOH, the temperature was controlled at 40°C for 6 hours, and the end point of the reaction was monitored by TLC until the disappearance of the raw material point. Cool to room temperature, filter with suction, wash with 5 ~ 10mL H 2 O and anhydrous C 2 h 5 The filter cake was washed with OH and vacuum dried to obtain the light yellow product 4-nitro-1,8-dimethylnaphthalene (II-1) with a yield of 91%. HPLC purity 98.5%. HRMS(ES+)C 12 h 12 NO 2 ([M+H]) + The theoretical value is 202.0868, and the measured value is 202.0868.

Embodiment 2

[0030]

[0031] 3.20g (20mmol, M=160.17) 1,8-dihydroxynaphthalene (I-2), 9.00g (24 mmol, M=375.13) Al(NO 3 ) 3 .9H 2 O was added to 15mL CH 3 COOH+15mL (CH 3 CO) 2 In O, the temperature was controlled at 20°C for 6 hours, and the other conditions and preparation steps were the same as in Example 1 to obtain the orange-yellow product 4-nitro-1,8-naphthalenediol (II-2), with a yield of 90%. HPLC purity 99.0%. HRMS(ES+)C 10 h 8 NO 4 ([M+H]) + The theoretical value is 206.0453, and the measured value is 206.0451.

Embodiment 3

[0033]

[0034] 3.16g (20mmol, M=158.20) 1,8-diaminonaphthalene (I-3), 9.48g (24 mmol, M=394.98) Bi(NO 3 ) 3 Added to 15mL CH 3 COOH+15mL (CH 3 CO) 2 In O, the temperature was controlled at 20°C for 6 hours. Other conditions and preparation steps were the same as in Example 1 to obtain the orange-red product 4-nitro-1,8-naphthalenediamine (II-3) with a yield of 93%. HPLC purity 99.0%. HRMS(ES+)C 10 h 10 N 3 o 2 ([M+H]) + The theoretical value is 204.0773, and the measured value is 204.0772.

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Abstract

The invention provides a preparation method of 1,8-disubstituted naphthalene mononitration derivative. The preparation method is characterized by comprising the following steps: S1, taking 1,8-disubstituted naphthalene as a raw material, taking main group metal nitrate as a nitration reagent, dissolving the 1,8-disubstituted naphthalene and the main group metal nitrate in an organic solvent, performing a nitration reaction under 10-60 DEG C for 4-10 h, and then monitoring by TLC (Thin layer chromatography) till a raw material point disappears to finish the reaction; S2, cooling a product obtained in step S1 to room temperature, performing suction filtration, washing filter cake with 5-10 mL of H2O and anhydrous C2H5OH separately, and performing vacuum drying to obtain the 1,8-disubstitutednaphthalene mononitration derivative. According to the preparation method of the 1,8-disubstituted naphthalene mononitration derivative, the product yield can reach 90%-95%; the product purity reaches 98.5%-99.6%; compared with the prior art, the preparation method has the characteristics of high product yield, high purity, low cost and simple process, and is easy to industrialize.

Description

technical field [0001] The invention belongs to the field of fine chemical industry, in particular to a preparation method of 1,8-disubstituted naphthalene mononitration derivatives. Background technique [0002] 1,8-disubstituted naphthalene is an important fine chemical raw material, which can be separated from petroleum refining and coal tar. Its nitrated products can be widely used in various industries such as dyes, medicines, pesticides, explosives and daily necessities. practical and economic value. At present, the industry still follows the traditional method of nitrification by mixed acid (sulfuric acid / nitric acid) more than one hundred years ago, but this process has defects such as no nitrification selectivity and serious environmental pollution. Today's clean and green nitrification technology is due to its high efficiency, high It has attracted extensive attention due to its selectivity and atom economy. [0003] Among the reported green nitrification technol...

Claims

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Application Information

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IPC IPC(8): C07C201/08C07C205/06C07C205/25C07C209/76C07C211/59C07C205/35C07C205/45C07D311/80C07D221/14C07D221/16C07D327/04
CPCC07C201/08C07C209/76C07D311/80C07D221/14C07D221/16C07D327/04C07C2603/20C07C205/06C07C205/25C07C211/59C07C205/35C07C205/45
Inventor 吴爱斌陈倩周五胡艳雄师春甜
Owner YANGTZE UNIVERSITY
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