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Method for synthesizing 1,5-diaminonaphthalene in one step by naphthalene

A technology of diaminonaphthalene and mixed solvent, applied in the field of organic synthesis, can solve the problems of complex process, environmental pollution and the like, and achieve the effects of simple process, short process and mild reaction conditions

Active Publication Date: 2017-07-14
XIANGTAN UNIV
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0005] Aiming at defects such as complex process and environmental pollution in the method for synthesizing 1,5-diaminonaphthalene in the prior art, the object of the present invention is to provide a one-step synthesis 1, which has simple steps, low cost of raw materials, and is friendly to the environment. 5-diaminonaphthalene method

Method used

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  • Method for synthesizing 1,5-diaminonaphthalene in one step by naphthalene

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Comparison scheme
Effect test

Embodiment 1

[0028] Weigh 0.05g of sodium metavanadate and 1.6g of hydroxylamine hydrochloride respectively, put them into a three-necked flask connected with a thermometer and a condenser tube, then measure 15mL of glacial acetic acid and 5mL of deionized water into the three-necked flask, and then place the three-necked flask In a constant temperature water bath, stir at 30°C for 20 minutes, then add 0.5 g of naphthalene, raise the temperature to 80°C, and stop the reaction after 4 hours of constant temperature reaction. The final product was obtained after post-processing the reaction liquid, and the mass of 1,5-diaminonaphthalene in the product was quantitatively analyzed by liquid chromatography external standard method, and the yield was 2.3%.

[0029] From figure 1 It can be seen from the figure that the reaction produces 1,5-diaminonaphthalene, wherein the retention time of 1,5-diaminonaphthalene is about 4.2 minutes, and the retention time of raw naphthalene is about 13.8 minutes....

Embodiment 2

[0031] Weigh 0.05g of sodium metavanadate and 1.6g of hydroxylamine hydrochloride respectively, put them into a three-necked flask connected with a thermometer and a condenser tube, then measure 20mL of glacial acetic acid and 5mL of deionized water into the three-necked flask, and then place the three-necked flask In a constant temperature water bath, stir at a constant temperature of 30°C for 20 minutes, then add 0.5g of naphthalene, raise the temperature to 80°C, and stop the reaction after 6 hours of constant temperature reaction. The final product was obtained after post-treatment of the reaction liquid, and the mass of 1,5-diaminonaphthalene in the product was quantitatively analyzed by liquid chromatography external standard method, which was 31.8 mg, and the yield was 5.15%.

Embodiment 3

[0033] Weigh 0.05g of sodium metavanadate and 1.6g of hydroxylamine hydrochloride respectively, put them into a three-necked flask connected with a thermometer and a condenser tube, then measure 20mL of glacial acetic acid and 5mL of deionized water into the three-necked flask, and then place the three-necked flask In a constant temperature water bath, stir at a constant temperature of 30°C for 20 minutes, then add 0.5g of naphthalene, raise the temperature to 60°C, and stop the reaction after 8 hours of constant temperature reaction. The final product was obtained after post-treatment of the reaction liquid, and the mass of 1,5-diaminonaphthalene in the product was quantitatively analyzed by liquid chromatography external standard method, which was 6.8 mg, and the yield was 1.1%.

[0034] This embodiment illustrates that the conversion rate of naphthalene is relatively low when the temperature is lower, and an appropriate temperature range is more conducive to improving the re...

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Abstract

The invention discloses a method for synthesizing 1,5-diaminonaphthalene by one step with naphthalene. The method is characterized in that in a mixed solvent of glacial acetic acid and water, naphthalene and hydroxylammonium salts carry out one-step reaction in the presence of catalysts, namely metavanadate and / or vanadium oxide, to generate 1,5-diaminonaphthalene. The method is low in cost, simple in process, short in flow and mild in reaction conditions, is environment-friendly and meets the industrial production requirements.

Description

technical field [0001] The invention relates to a method for one-step synthesis of 1,5-diaminonaphthalene from naphthalene, which belongs to the field of organic synthesis. Background technique [0002] 1,5-diaminonaphthalene, also known as 1,5-naphthalene diamine, is an extremely important organic raw material, widely used in pharmaceuticals, agricultural chemicals, dyes, surfactants, rubber additives, resins, photosensitive materials Production, especially for the synthesis of 1,5-naphthalene diisocyanate, and then the preparation of polyurethane. Polyurethane is widely used in many fields such as light industry, chemical industry, electronics, textile, medical treatment, construction, building materials, national defense, aerospace, aviation, etc., and the development prospect is very broad. The demand for intermediate raw materials such as 1,5-naphthalene diamine bigger. [0003] The existing synthesis methods of 1,5-diaminonaphthalene mainly include naphthalene nitrat...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/58C07C209/02
CPCC07C209/02C07C211/58
Inventor 刘平乐王恺君熊伟郝芳罗和安
Owner XIANGTAN UNIV
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