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Preparation method of 1,5-dinitronaphthalene and 1,8-dinitronaphthalene

A dinitronaphthalene and nitrogen dioxide technology, applied in the field of synthesis of 1,5-dinitronaphthalene and 1,8-dinitronaphthalene, can solve poor safety performance, low atom economy and environmental pollution Serious problems, to achieve the effect of increasing yield and selectivity, improving atom utilization, and reducing environmental pollution

Inactive Publication Date: 2012-12-19
ANHUI HUAIHUA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] With the development of environmental economy, the shortcomings of the above methods are becoming more and more manifested, mainly as follows: (1) the atom economy is not high; (2) the reaction selectivity is poor, a large amount of organic by-product waste is formed, and the environmental pollution is serious; ( 3) High energy consumption, a large amount of acid gas and strong inorganic waste acid need to be treated; (4) Strong acid environment is highly corrosive to equipment, and equipment investment costs are high; (5) Strong acid environment is prone to oxidation side reactions, rapid heat release, and safety performance Difference
In view of the increasing demand for dinitronaphthalene, with the development of environmental economy, the traditional production method of dinitronaphthalene is not sustainable and must be replaced by a more environmentally friendly method

Method used

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  • Preparation method of 1,5-dinitronaphthalene and 1,8-dinitronaphthalene
  • Preparation method of 1,5-dinitronaphthalene and 1,8-dinitronaphthalene
  • Preparation method of 1,5-dinitronaphthalene and 1,8-dinitronaphthalene

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Experimental program
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Embodiment 1

[0021] In a 50 mL three-necked flask, add 0.128 g of naphthalene, 5.0 mL of acetonitrile, 0.100 g of HZSM-11, 2.0 mL of nitrogen dioxide, stir magnetically in an oxygen atmosphere, and react at room temperature for 12 hours. After the reaction time has elapsed, the reaction is terminated with deionized water. The mixture was filtered through a glass funnel to remove the catalyst. The filtrate was rotary evaporated in vacuo to obtain a crude product, which was washed three times with 5% aqueous sodium bicarbonate solution, and then washed with distilled water until the crude product was neutral. Nitrobenzene was used as internal standard for HPLC analysis, and the content of each isomer component of nitration products was calculated by internal standard method. The mass of 1,5-dinitronaphthalene and 1,8-dinitronaphthalene is 0.160g, and the yield is 73.0%, of which the mass of 1,5-dinitronaphthalene is 0.109g, and the mass fraction is 68.1%; 1 , The mass of 8-dinitronaphthale...

Embodiment 2

[0024] In a 50 mL three-necked flask, add 0.128 g of naphthalene, 5.0 mL of acetonitrile, 0.100 g of Hβ-500, and 2.0 mL of nitrogen dioxide, stir magnetically in an oxygen atmosphere, and react at room temperature for 12 hours. After the reaction time has elapsed, the reaction is terminated with deionized water. The mixture was filtered through a glass funnel to remove the catalyst. The filtrate was rotary evaporated in vacuo to obtain a crude product, which was washed three times with 5% aqueous sodium bicarbonate solution, and then washed with distilled water until the crude product was neutral. After drying, carry out HPLC analysis with nitrobenzene as the internal standard, and calculate the content of each isomer component of the nitration product with the internal standard method. The mass of 1,5-dinitronaphthalene and 1,8-dinitronaphthalene is 0.177g, and the yield is 81.4%, of which the mass of 1,5-dinitronaphthalene is 0.131g, and the mass fraction is 74.0%; 1 , The...

Embodiment 3

[0027] In a 50 mL three-necked flask, add 0.128 g of naphthalene, 5.0 mL of acetonitrile, 0.200 g of HY, and 2.0 mL of nitrogen dioxide, stir magnetically in an oxygen atmosphere, and react at room temperature for 12 hours. After the reaction time has elapsed, the reaction is terminated with deionized water. The mixture was filtered through a glass funnel to remove the catalyst. The filtrate was rotary evaporated in vacuo to obtain a crude product, which was washed three times with 5% aqueous sodium bicarbonate solution, and then washed with distilled water until the crude product was neutral. After drying, carry out HPLC analysis with nitrobenzene as internal standard, and calculate the content of each isomer component after nitration of naphthalene with internal standard method. The mass of 1,5-dinitronaphthalene and 1,8-dinitronaphthalene is 0.139g, and the yield is 63.8%. Among them, the mass of 1,5-dinitronaphthalene is 0.096g, and the mass fraction is 69.1%; the mass o...

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Abstract

The invention relates to a preparation method of 1,5-dinitronaphthalene and 1,8-dinitronaphthalene. The preparation method comprises the steps of: dissolving naphthalene into an organic solvent to prepare a solution; and reacting the solution with nitrogen dioxide in a catalyst and an oxygen atmosphere. Dinitronaphthalene is prepared by using nitrogen dioxide as a nitration agent, instead of nitric acid and sulfuric acid, and the naphthalene as a basic material, and thus the preparation method is a non-acidic cleaning method, and is mild in reaction conditions, good in selectivity, and high in atom efficiency and the environment is clean.

Description

technical field [0001] The present invention relates to the synthesis of 1,5-dinitronaphthalene and 1,8-dinitronaphthalene. Background technique [0002] 1,5-Dinitronaphthalene and 1,8-Dinitronaphthalene are important chemical intermediates, which are widely used in the preparation of dyes, pigments and high-energy materials. 1,5-Dinitronaphthalene is also the precursor of 1,5-naphthalene diisocyanate, 1,5-naphthalene diisocyanate has a higher melting point, and the polyurethane synthesized from it has high hardness, good resilience and heat resistance Good performance, excellent dynamic performance, good wear resistance, etc., can be used in workplaces where ordinary polyurethane cannot meet the requirements or is prematurely damaged, such as high temperature and oily environments, so it is mostly used as a raw material for the synthesis of advanced polyurethane. 1,8-Dinitronaphthalene is also the precursor of 1,8-diaminonaphthalene, which is mainly used in the production ...

Claims

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Application Information

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IPC IPC(8): C07C201/08C07C205/06
Inventor 彭新华韩松汪浩才苏传好朱志峰
Owner ANHUI HUAIHUA
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