Preparation method of 1,8-disubstituted naphthalene series polycyclic aromatic hydrocarbon mononitration derivative

A fused-ring aromatic hydrocarbon and disubstituted technology, which is applied in the field of preparation of 1,8-disubstituted naphthalene-based condensed-ring aromatic hydrocarbon mononitration derivatives, can solve problems such as poor selectivity, poor substrate universality, and many wastes, and achieve low cost Low, high product yield and high purity effect

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

AI Technical Summary

Problems solved by technology

The current industrial preparation method still uses the traditional mixed acid nitration, but this process has obvious defects such as poor selectivity, many wastes, strong corrosion and serious environmental pollution, while the clean, green, efficient, high selectivity and atom-economical nitration Technology is getting more and more attention
[0003] Among the reported green nitrification technologies, such as solid acid catalysis and Lewis acid catalysis, etc., some achievements have been made in replacing sulfuric acid to reduce corrosion and three waste emissions, catalyst recovery and recycling, but there are still some shortcomings in these processes. , such as the difficulty of industrial promotion and application, the poor universality of substrates, and how to solve the problems of the relationship between function, cost and greenness

Method used

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  • Preparation method of 1,8-disubstituted naphthalene series polycyclic aromatic hydrocarbon mononitration derivative
  • Preparation method of 1,8-disubstituted naphthalene series polycyclic aromatic hydrocarbon mononitration derivative
  • Preparation method of 1,8-disubstituted naphthalene series polycyclic aromatic hydrocarbon mononitration derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]

[0027] 3.12g (20mmol, M=156.23) 1,8-dimethylnaphthalene (I-1), 9.29g (23 mmol, M=404.00) Fe(NO 3 ) 3 9H 2 O was added to 26mL CH 3 In COOH, the temperature was controlled at 40°C for 5 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, and use a small amount of 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 92%. HPLC purity 98.6%. HRMS(ES+)C 12 h 12 NO 2 ([M+H]) + The theoretical value is 202.0868, and the measured value is 202.0866.

Embodiment 2

[0029]

[0030] 3.20g (20mmol, M=160.17) 1,8-dihydroxynaphthalene (I-2), 5.35g (23 mmol, M=232.59) Cu(NO 3 ) 2 2.5H 2 O was added to 13mL CH 3 COOH+13 mL(CH 3 CO) 2 In O, the temperature was controlled at 25°C for 5 h. 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 91%. HPLC purity 99.2%. HRMS(ES+)C 10 h 8 NO 4 ([M+H]) + The theoretical value is 206.0453, and the measured value is 206.0453.

Embodiment 3

[0032]

[0033] 3.16g (20mmol, M=158.20) 1,8-diaminonaphthalene (I-3), 9.29g (23 mmol, M=404.00) Fe(NO 3 ) 3 9H 2 O was added to 13mL CH 3 COOH+13mL (CH 3 CO) 2 In O, the temperature was controlled at 25°C for 5 h. 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 94%. 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 204.0774.

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Abstract

The invention provides a preparation method of 1,8-disubstituted naphthalene series polycyclic aromatic hydrocarbon mononitration derivative. The preparation method is characterized by comprising thefollowing steps: S1, dissolving 1,8-disubstituted naphthalene series polycyclic aromatic hydrocarbon and subgroup metal nitrate in an organic solvent, performing a nitration reaction under 10-60 DEG Cfor 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 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-disubstituted naphthalene series polycyclic aromatic hydrocarbon mononitration derivative. According to the preparation method of the 1,8-disubstituted naphthalene series polycyclic aromatic hydrocarbon mononitration derivative, the product yield is 93%-96%; theproduct purity is 98%-99.5%; 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 technical field of fine chemicals, and in particular relates to a preparation method of 1,8-disubstituted naphthalene series fused-ring aromatic hydrocarbon mononitration derivatives. Background technique [0002] 1,8-disubstituted naphthalene-based fused-ring aromatics are one of the important fine chemical raw materials, mainly derived from by-products in petroleum refining and coal tar, and their nitrated products can be widely used in dyes, medicines, pesticides, explosives and daily necessities, etc. Various industries have important practical value and economic value. The current industrial preparation method still uses the traditional mixed acid nitration, but this process has obvious defects such as poor selectivity, many wastes, strong corrosion and serious environmental pollution, while the clean, green, efficient, high selectivity and atom-economical nitration Technology is gradually being valued. [0003] Amon...

Claims

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Application Information

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IPC IPC(8): C07C201/08C07C205/06C07C205/25C07C209/76C07C211/59C07C205/35C07D311/80C07D221/14C07D221/16C07D327/04
CPCC07C201/08C07C209/76C07D221/14C07D221/16C07D311/80C07D327/04C07C2603/20C07C205/06C07C205/25C07C211/59C07C205/35
Inventor 郭莉吴爱斌秦少雄
Owner YANGTZE UNIVERSITY
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