Aromatic heterocyclic compound 2,4,6,8-tetraamino-1,5-naphthalenediol hydrochloride and synthesis method thereof

Abstract

The invention relates to an aromatic heterocyclic compound 2,4,6,8-tetraamino-1,5-naphthalenediol hydrochloride and a synthesis method thereof, and belongs to the technical field of organic compound preparation. A purpose of the present invention is to solve the problems of poor performance, harsh and complicated synthesis conditions and high cost of the existing aromatic heterocyclic polymer monomers. According to the present invention, the chemical formula of the aromatic heterocyclic compound 2,4,6,8-tetraamino-1,5-naphthalenediol hydrochloride is C10H16Cl4N4O2; the preparation method comprises: preparing a 2,4,6,8-tetranitro-1,5-naphthalenediol crude product, preparing a 2,4,6,8-tetranitro-1,5-naphthalenediol pure product, dissolving the pure product in absolute ethanol, adding a Pd / Ccatalyst, carrying out a hydrogenation reaction, filtering out the catalyst, introducing concentrated hydrochloric acid containing stannous chloride into the filtrate, is crystallizing, filtering, anddrying; the synthesized monomer has characteristics of novel structure and good physical and chemical properties; and the preparation method has characteristics of simple method, short cycle, high conversion rate, no pollution and low cost, and is used in the field of synthesis of aromatic heterocyclic polymer monomers.

Description

technical field

[0001] The invention relates to the technical field of organic compound preparation. Background technique

[0002] Aromatic heterocyclic polymers are a class of heat-resistant polymer materials developed by the United States and the former Soviet Union in the mid-1950s. Aromatic heterocyclic macromolecules refer to the main chain of macromolecules composed of benzene ring, naphthalene ring and other aromatic rings and / or heterocyclic rings and some linking groups, such as -O-, -S-, -CO-, -SO 2 -, -CH 2 -, -C(CH 3 ) 2 -,—C(CF 3 ) 2 —, -COO-, -CONH-, etc. or polymer compounds composed only of single bond connections. Many aromatic heterocyclic polymers are functional polymer materials. They not only have good heat resistance, but also have high strength and light weight properties. They are indispensable materials in important high-tech fields such as aerospace, electronics, and high-speed rail transportation. Improving the processability of high-perform...

Examples

specific Embodiment approach 1

[0018] Specific embodiment one: In this embodiment, a kind of aromatic heterocyclic compound 2,4,6,8-tetraamino-1,5-naphthalenediol hydrochloride, its chemical formula is: C 10 h 16 Cl 4 N 4 o 2 ; Its molecular formula is:

specific Embodiment approach 2

[0019] Specific embodiment two: In this embodiment, a method for synthesizing aromatic heterocyclic compound 2,4,6,8-tetraamino-1,5-naphthalenediol hydrochloride is realized according to the following steps:

[0020] 1. In a three-necked flask, dissolve 1,5-naphthalenediol in concentrated sulfuric acid with a mass concentration of 80-98%, then add mixed acid dropwise, and obtain 2,4,6 after stirring reaction, suction filtration, water washing, and drying. , 8-tetranitro-1,5-naphthalenediol crude product, redissolved in an organic solvent for recrystallization to obtain bright yellow needle crystals, collected by suction filtration to obtain 2,4,6,8-tetranitro - Pure 1,5-naphthalenediol;

[0021] 2. In a high-pressure reactor, the pure product of 2,4,6,8-tetranitro-1,5-naphthalenediol is dissolved in absolute ethanol as a substrate, and then a Pd / C catalyst is added for hydrogenation reaction, After the reaction is completed, filter, remove the Pd / C catalyst, and then pass int...

specific Embodiment approach 3

[0024] Embodiment 3: This embodiment is different from Embodiment 2 in that the weight ratio of 1,5-naphthalenediol to concentrated sulfuric acid with a mass concentration of 80-98% in step 1 is 1:(2-10). Other steps and parameters are the same as in the second embodiment.

technical field

[0001] The invention relates to the technical field of organic compound preparation. Background technique

[0002] Aromatic heterocyclic polymers are a class of heat-resistant polymer materials developed by the United States and the former Soviet Union in the mid-1950s. Aromatic heterocyclic macromolecules refer to the main chain of macromolecules composed of benzene ring, naphthalene ring and other aromatic rings and / or heterocyclic rings and some linking groups, such as -O-, -S-, -CO-, -SO 2 -, -CH 2 -, -C(CH 3 ) 2 -,—C(CF 3 ) 2 —, -COO-, -CONH-, etc. or polymer compounds composed only of single bond connections. Many aromatic heterocyclic polymers are functional polymer materials. They not only have good heat resistance, but also have high strength and light weight properties. They are indispensable materials in important high-tech fields such as aerospace, electronics, and high-speed rail transportation. Improving the processability of high-perform...

Examples

specific Embodiment approach 1

[0018] Specific embodiment one: In this embodiment, a kind of aromatic heterocyclic compound 2,4,6,8-tetraamino-1,5-naphthalenediol hydrochloride, its chemical formula is: C 10 h 16 Cl 4 N 4 o 2 ; Its molecular formula is:

specific Embodiment approach 2

[0019] Specific embodiment two: In this embodiment, a method for synthesizing aromatic heterocyclic compound 2,4,6,8-tetraamino-1,5-naphthalenediol hydrochloride is realized according to the following steps:

[0020] 1. In a three-necked flask, dissolve 1,5-naphthalenediol in concentrated sulfuric acid with a mass concentration of 80-98%, then add mixed acid dropwise, and obtain 2,4,6 after stirring reaction, suction filtration, water washing, and drying. , 8-tetranitro-1,5-naphthalenediol crude product, redissolved in an organic solvent for recrystallization to obtain bright yellow needle crystals, collected by suction filtration to obtain 2,4,6,8-tetranitro - Pure 1,5-naphthalenediol;

[0021] 2. In a high-pressure reactor, the pure product of 2,4,6,8-tetranitro-1,5-naphthalenediol is dissolved in absolute ethanol as a substrate, and then a Pd / C catalyst is added for hydrogenation reaction, After the reaction is completed, filter, remove the Pd / C catalyst, and then pass int...

specific Embodiment approach 3

[0024] Embodiment 3: This embodiment is different from Embodiment 2 in that the weight ratio of 1,5-naphthalenediol to concentrated sulfuric acid with a mass concentration of 80-98% in step 1 is 1:(2-10). Other steps and parameters are the same as in the second embodiment.

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