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Green synthetic method of trinitrophloroglucinol and application thereof

A technology of trinitrophloroglucinol and phloroglucinol, which is applied to the preparation of nitro compounds, nitrated explosive components, offensive equipment, etc., can solve the problems of strong corrosion, pollution, severe conditions, etc., and achieve low corrosion , Overcoming serious pollution and easy operation

Active Publication Date: 2015-09-23
QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In order to solve the deficiencies in the prior art, the present invention provides a green synthesis method of trinitrophloroglucinol, a precursor of an insensitive energetic material, to overcome the serious pollution, strong corrosion, and conditions existing in the existing synthesis methods. For serious problems, the technical solution adopted is as follows:

Method used

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  • Green synthetic method of trinitrophloroglucinol and application thereof
  • Green synthetic method of trinitrophloroglucinol and application thereof
  • Green synthetic method of trinitrophloroglucinol and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0043]Weigh phloroglucinol (50mmoL), place it in a 250mL round bottom flask, add ethanol (80mL), and stir to dissolve. Under the condition of ice bath, measure n-propyl nitrite (167mmoL), slowly add it dropwise to the above reaction solution, stir in ice bath for 0.5h, rise to room temperature and stir for 0.5h. Ethanol was evaporated to dryness under reduced pressure, then 10% aqueous sodium hydroxide solution (120 mL) was added, stirred to dissolve, 30% hydrogen peroxide solution (300 mmoL) was measured, added dropwise to the above reaction solution, and stirred at room temperature for 8 h. Under ice-bath conditions, the pH of the reaction solution was adjusted to pH=1-2 with concentrated hydrochloric acid, extracted with ethyl acetate (50mL×3), the organic phases were combined, washed with water (50mL), and evaporated to dryness under reduced pressure to obtain yellow crystals Trinitrophloroglucinol, yield 77.5%.

[0044] The melting point of the obtained product is 165-16...

Embodiment 2

[0046] Weigh phloroglucinol (50mmoL), place it in a 250mL round bottom flask, add ethanol (80mL), and stir to dissolve. Under the condition of ice bath, measure n-propyl nitrite (150mmoL), slowly add dropwise to the above reaction solution, stir in ice bath for 0.5h, rise to room temperature and stir for 0.5h. Ethanol was evaporated to dryness under reduced pressure, then 10% aqueous sodium hydroxide solution (120 mL) was added, stirred to dissolve, 30% hydrogen peroxide solution (300 mmoL) was measured, added dropwise to the above reaction solution, and stirred at room temperature for 8 h. Under ice-bath conditions, the pH of the reaction solution was adjusted to pH=1-2 with concentrated hydrochloric acid, extracted with ethyl acetate (50mL×3), the organic phases were combined, washed with water (50mL), and evaporated to dryness under reduced pressure to obtain yellow crystals Trinitrophloroglucinol, yield 58.0%.

Embodiment 3

[0048] Weigh phloroglucinol (50mmoL), place it in a 250mL round bottom flask, add ethanol (80mL), and stir to dissolve. Under ice-bath conditions, measure n-propyl nitrite (200mmoL), slowly dropwise add to the above reaction solution, stir in ice-bath for 0.5h, rise to room temperature and stir for 0.5h. Ethanol was evaporated to dryness under reduced pressure, then 10% aqueous sodium hydroxide solution (120 mL) was added, stirred to dissolve, 30% hydrogen peroxide solution (300 mmoL) was measured, added dropwise to the above reaction solution, and stirred at room temperature for 8 h. Under ice-bath conditions, the pH of the reaction solution was adjusted to pH=1-2 with concentrated hydrochloric acid, extracted with ethyl acetate (50mL×3), the organic phases were combined, washed with water (50mL), and evaporated to dryness under reduced pressure to obtain yellow crystals Trinitrophloroglucinol, yield 78.6%.

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Abstract

The invention discloses a green synthetic method of trinitrophloroglucinol and application thereof, and belongs to the technical field of organic synthesis. The method provided by the invention comprises the following steps of dropwise adding nitrite ester into a phloroglucinol alcohol solution to carry out a nitrosation reaction, afterwards, evaporating an alcoholic solvent, adding a sodium hydroxide solution for dissolving an obtained product, and then dropwise adding a hydrogen peroxide solution into an obtained mixture for carrying out an oxidation reaction, regulating the pH (potential of hydrogen) of an obtained new mixture, then extracting the pH-regulated mixture by utilizing an organic solvent, and washing and concentrating an obtained final product to obtain the trinitrophloroglucinol. The green synthetic method of trinitrophloroglucinol is little in pollution, low in corrosion, and mild in reaction conditions, and does not need a catalyst, and the defects of serious pollution, equipment corrosion, severe condition and the like in a conventional synthetic method are overcome. The green synthetic method of the trinitrophloroglucinol is suitable for the synthesis of the trinitrophloroglucinol.

Description

technical field [0001] The invention relates to a green synthesis method and application of trinitrophloroglucinol, belonging to the technical field of organic synthesis. Background technique [0002] Trinitrophloroglucinol (TNPG) is a strong acidic aromatic phenolic compound (Formula 1), which can form metal salts with strong explosive properties with a variety of metals, among which trinitrophloroglucinol lead It is an important primary explosive. In addition, it is also a synthetic insensitive, high-energy explosive 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) and a new type of explosive diaminopicric acid ammonium (ADAP ) important intermediates. [0003] [0004] There are many synthetic methods for trinitrophloroglucinol. At present, the route of synthesizing trinitrophloroglucinol by nitration of phloroglucinol is the most mature. Due to the strong passivation effect of the nitro group, the nitro group that reacts first during nitration will greatly reduce the rea...

Claims

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Application Information

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IPC IPC(8): C07C205/24C07C201/08C06B25/22
Inventor 咸漠孙伟之张汝兵曹玉锦
Owner QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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