Method for controlling crystal form of 2, 4-dinitroanisole

A technology of dinitroanisole and dinitrochlorobenzene, which is applied in the field of controlling the crystal form of 2,4-dinitroanisole, and can solve problems such as safety accidents, lack of exact conditions, and volume changes of molten castings. To achieve the safety of the transportation process and reduce the volume change of the molten casting body

Pending Publication Date: 2022-05-17
ZHONGBEI UNIV +1
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Problems solved by technology

For example, in 1987, Nyburg, S. C et al reported the crystal structure of DNAN in "Structures of 2,4-Dinitroanisole and 2,6-Dinitroanisole" (Document 1), including unit cell parameters, symmetry, bond length and angle and other data, but no mention of the crystal form
In 1992, Malinovskii, S. T. et al. reported the crystal structure of DNAN and Nyburg et al. The similar crystal parameters published by the author clearly show that its melting point is 94-95°C, but there is still no mention of the crystal form.
In 2006, Davies, P. J. et al. "Characterisation of 2,4-Dinitroanisole: An Ingredient for Usein Low Sensitivity Melt Cast Formulations" (Document 3) reported that DNAN has two crystal forms, with melting points of 94-96°C and 86- 88°C, but crystal parameters are not provided
In 2007, Xue Gang from Hebei University of Technology et al. in "Crystal structure of 2,4-dinitroanisole, C 7 h 6 N 2 o 5 "(Document 4) reported a crystal structure different from Malinovskii, S. T., provided crystal parameters, but did not mention the melting point
In 2014, Wang Hongxing and others from Xi’an Modern Chemistry Research Institute used Perkin-Elmer DSC-2C differential scanning calorimeter to analyze the endothermic peak at 95.6°C when studying the casting performance and thermal safety performance of DNAN, and the melting point was obtained by fitting calculation. 94.5°C, but no product crystal form is mentioned
In 2016, Hubei Dongfang Chemical Co., Ltd.’s invention patent (Patent No. CN201610317074.7) of “A Method for Continuous Synthesis of 2,4-Dinitroanisole” mentioned a continuous synthesis of 2,4-Dinitroanisole The method of nitroanisole, the melting point of DNAN obtained is 96°C, but no crystal form is mentioned
ChagitDenekamp et al. only qualitatively stated that the β crystal form is easy to appear during supercooled crystallization, but they lack exact conditions. They did not directly obtain pure α-DNAN and β-DNAN according to the report of Takahashi and Tamura et al.
However, the accidental appearance of different crystal forms is risky for the application of DNAN. If crystal form doping occurs in the actual production process, it may cause volume changes or defects in the molten cast, resulting in unstable performance and possible Increase the sensitivity of explosives, which will have adverse effects on the subsequent processing, storage, and transportation processes, and even cause danger and cause safety accidents

Method used

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  • Method for controlling crystal form of 2, 4-dinitroanisole
  • Method for controlling crystal form of 2, 4-dinitroanisole

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Embodiment 1

[0037] A method for controlling 2,4-dinitroanisole crystal form, comprising the following steps:

[0038] Weigh 5 g of 2,4-dinitrochlorobenzene (CDB) and add it to 20 g of methanol, raise the temperature to 50°C to dissolve CDB completely, keep the temperature constant, and prepare a CDB methanol solution; prepare 3.5 g with a mass fraction of 30 % sodium hydroxide aqueous solution, mix it with 3 g methanol, and prepare methanol lye; add methanol lye dropwise to the CDB methanol solution, and control the temperature at 50°C during the dropwise addition process; after the dropwise addition, Incubate at 50°C for 20 min; reduce the reaction solution to room temperature to precipitate crystals, filter to obtain a filter cake; wash the filter cake with 50mL deionized water at room temperature, repeat 2-3 times until the filtrate is neutral, filter to obtain a filter cake ; Dry the filter cake at 17°C for 4 hours, the melting point of the product is 85.6-86.2°C, and the product is β...

Embodiment 2

[0040] A method for controlling 2,4-dinitroanisole crystal form, comprising the following steps:

[0041] Weigh 30 g of 2,4-dinitrochlorobenzene (CDB) and add it to 180 g of methanol, raise the temperature to 50°C to dissolve CDB completely, keep the temperature constant, and prepare CDB methanol solution; prepare 24 g of 30% mass fraction Mix it with 30 g of methanol to prepare methanol lye; add methanol lye dropwise at a constant speed to the CDB methanol solution, and control the reaction temperature at 50°C during the dropwise addition; after the dropwise addition, Incubate at 60°C for 40 min; lower the reaction solution to room temperature to precipitate crystals, filter to obtain a filter cake; wash the filter cake with 900mL deionized water at room temperature, repeat 2-3 times until the filtrate is neutral, filter to obtain a filter cake ; Dry the filter cake at 25°C for 3 hours, the melting point of the product is 94.6-96.7°C, and the product is α-DNAN.

Embodiment 3

[0043] A method for controlling 2,4-dinitroanisole crystal form, comprising the following steps:

[0044] Weigh 3 g of 2,4-dinitrochlorobenzene (CDB) and add it to 21 g of methanol, raise the temperature to 65°C to dissolve CDB completely, keep the temperature constant, and prepare a CDB methanol solution; prepare 2 g with a mass fraction of 30 % sodium hydroxide aqueous solution, mix it with 3 g methanol, and prepare methanol lye; add methanol lye dropwise to the CDB methanol solution, and control the temperature at 65°C during the dropwise addition; after the dropwise addition, Incubate at 65°C for 40 min; reduce the reaction solution to room temperature to precipitate crystals, filter to obtain a filter cake; wash the filter cake with 100mL deionized water at room temperature, repeat 2-3 times until the filtrate is neutral, filter to obtain a filter cake ; Dry the filter cake at 50°C for 2.5 hours, the melting point of the product is 93.7-95.6°C, and the product is α-DNAN. ...

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Abstract

The invention relates to a method for controlling the crystal form of 2, 4-dinitroanisole, and belongs to the technical field of energetic material synthesis. According to the method disclosed by the invention, products alpha-DNAN and beta-DNAN with different crystal forms are obtained by adopting the same raw materials of CDB, sodium hydroxide and methanol and controlling a synthesis process. According to the method disclosed by the invention, synthesis and preparation conditions of the alpha crystal form and the beta crystal form are defined, and a guarantee is provided for safe and reliable use of the 2, 4-dinitroanisole in weaponry. According to the method disclosed by the invention, in the actual production process, the situation of unstable performance of the casting body caused by volume change of the casting body due to crystal form doping can be reduced, and a safer guarantee is provided for subsequent product treatment, storage and transportation processes.

Description

technical field [0001] The invention relates to the field of organic chemical technology, especially the field of synthesis of energetic materials, in particular to a method for controlling the crystal form of 2,4-dinitroanisole. Background technique [0002] 2,4-Dinitroanisole, code name DNAN, molecular formula C 7 h 6 N 2 o 5 , the molecular weight is 198.14, and the structural formula is: [0003] . [0004] DNAN is a white or pale yellow needle-like crystal, which can be used as a pesticide, dye intermediate or energetic material in different fields, especially as a new type of melt-cast explosive carrier, which is considered to have important application prospects. [0005] It has been 170 years since DNAN was first synthesized in 1849. Due to its medium energy, it has no advantages as a main explosive, so it was ignored for a long time after World War II. Compared with TNT, DNAN has better safety performance. Therefore, with the improvement of weapons and equip...

Claims

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Application Information

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IPC IPC(8): C07C201/12C07C205/37
CPCC07C201/12C07B2200/13C07C205/37
Inventor 陈丽珍陈聪李晓王建龙李翀潘红霞肖芸陈军
Owner ZHONGBEI UNIV
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