Synthesis of 1‐Amino‐2,4‐Dinitroimidazole Optimized by Online Infrared Spectroscopy and its Energetic Properties

Qu, Yanyang; Ya, Chen; Yu, Chang; Ma, Qing; Wang, Jun; Huang, Jingyun; Yang, Guangcheng

doi:10.1002/cplu.201600481

Cited by 5 publications

(5 citation statements)

References 24 publications

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“…37,38 Conversely, 1,4-dinitroimidazole (1,4-DNI, Scheme 1), belonging to a nitrogen-rich heterocyclic compound, has a low sensitivity with appropriate power. 39 Additionally, 1,4-DNI is more powerful than TNT, a traditional nitroaromatic explosive with low energy. Therefore, in view of the reduced power of the abovementioned CL-20/TNT cocrystal, we use 1,4-DNI as a new coformer instead of TNT in order to improve the power of the CL-20 cocrystals.…”

Section: Introductionmentioning

confidence: 54%

“…CL-20 (Scheme ), as one of the most powerful explosives, exhibits high energy density, whereas it is more sensitive to external stimuli, such as impact, friction, and shock waves, seriously hindering its practical applications. , Conversely, 1,4-dinitroimidazole (1,4-DNI, Scheme ), belonging to a nitrogen-rich heterocyclic compound, has a low sensitivity with appropriate power . Additionally, 1,4-DNI is more powerful than TNT, a traditional nitroaromatic explosive with low energy.…”

Section: Introductionmentioning

confidence: 99%

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High Energy Explosive with Low Sensitivity: A New Energetic Cocrystal Based on CL-20 and 1,4-DNI

Tan

Yang

Wang

et al. 2019

Crystal Growth & Design

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A new 1:1 cocrystal explosive composed of 2,4,6,8,10,12-hexanitrohexaazaiso-wurtzitane (CL-20) and 1,4-dinitroimidazole (1,4-DNI) was synthesized through cocrystallization by slow solvent evaporation. The cocrystal has a crystal density of 1.922 g/cm3 at 296 K and belongs to the orthorhombic system with P212121 space group. The properties of the cocrystal including thermal stability, impact sensitivity, and detonation performances were studied. DSC test shows that the cocrystal has a melting point of 115 °C with a decomposition temperature of 253 °C, suggesting an excellent thermal stability. Furthermore, the cocrystal exhibits an impact energy with 50% ignition probability of 10 J, showing a substantial reduction in impact sensitivity compared to pure CL-20 and HMX. Besides, the predicted detonation velocity and detonation pressure of the cocrystal are 9242 m/s and 39.01 GPa, respectively, which are similar to those of HMX. Therefore, the CL-20/1,4-DNI cocrystal may be an attractive high energy explosive with low sensitivity and, thus, may act as a promising explosive candidate instead of HMX for low vulnerability formulations in the future.

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Section: Introductionmentioning

confidence: 54%

Section: Introductionmentioning

confidence: 99%

High Energy Explosive with Low Sensitivity: A New Energetic Cocrystal Based on CL-20 and 1,4-DNI

Tan

Yang

Wang

et al. 2019

Crystal Growth & Design

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“…ADNI has good detonation performance. The detonation velocity was 8421 m⋅s −1 as determined by EXPLO5 v6.02 . Estane was selected as a binder and ADNI for granulation at a mass ratio of 2.5%:97.5%.…”

Section: Detonation Propertiesmentioning

confidence: 99%

“…This work expands our efforts in the preparation of ADNI (N‐amino‐2,4‐dinitroimidazole) molecules as detonation tools. (Scheme ) Here, we report the sensitivity of short impulse shock waves of ADNI. We then measured their compatibility, shock wave sensitivity, thermal stability, detonation, and sensitivity performance.…”

Section: Introductionmentioning

confidence: 99%

The Preparation and Properties of Submicrometer‐Sized N‐Amino‐2,4‐dinitroimidazole (ADNI): A Novel and Promising Initiating Explosive for Applications in Short Pulse Initiation Slapper Detonators

Wang

et al. 2018

ChemistrySelect

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We describe for the first time a spray‐recrystallization method to prepare sub‐micrometer N‐amino‐2,4‐dinitroimidazole (ADNI) and test its critical diameters below 3 mm. The uniform sub‐micrometer ADNI has better sensitivity to short impulse shock waves with the 50% and 99.9% initiation currents at 2.45 kA and 2.67 kA, respectively, which is much better than sub‐micrometer LLM‐105 (3.11 kA and 3.46 kA, respectively) and DAAF (3.7 kA and 4.75 kA, respectively). The detonation velocity for ADNI (7.8 km⋅s−1 at a density of 1.67 g⋅cm−3) is greater than that of LLM‐105 (7.54 km⋅s−1 at the density of 1.63 g⋅cm−3) and haxanitrostilbene (HNS) (6.8 km⋅s−1). ADNI also has a higher decomposition temperature (Td =265.8 °C) and a better thermal stability (5S shotpoint of 312 °C) with low impact, friction, and electric spark sensitivities (>40 N, >360 N, and 2.20 J). These metrics are comparable to LLM‐105 (0–30 N, >360 N, and 1.02 J) and HNS (26 N, 240 N, and 1.77 J). The high stability and good detonation properties of sub‐micrometer ADNI clearly shows that it is insensitive to impact stimulus and long pulse stimulation, while also being sensitive to short impulse shock waves. This suggests that it is a promising initiating explosive for slapper detonators.

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“…However, it has a high sensitivity. In order to overcome this defect, CL-20 is co-crystalized with some low sensitive energetic compounds such as 1,4-Dinitroimidazole(1,4-DNI) [3][4].…”

Section: Introductionmentioning

confidence: 99%

Crystal morphology prediction of CL-20 and 1,4-DNI co-crystal at different temperatures

Song

Zhao

et al. 2023

J Mol Model

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Using the attachment energy (AE) model and molecular dynamics (MD) methods, the morphologies of hexanitrohexaazaisowurtzitane (CL-20) and 1,4-dinitroimidazole (1,4-DNI) co-crystal under vacuum or solvent at different temperatures were predicted. The CL-20/1,4-DNI co-crystal has six important growth crystal planes: (002), ( 011), ( 101), (11-1), (110), ( 111). The area of ( 002), ( 101), and (011) planes account for a relatively large proportion, which are important crystal planes that affect the crystal morphology. At the same time, by calculating the interaction energy between the solvent and the crystal plane and the attachment energies under the influence of the solvent at 298 K, 320 K, 340 K, 360 K and 380 K were predicted. The crystal habits at different temperatures were simulated. The simulation results showed that the crystal plane attachment energy of CL-20 and 1,4-DNI co-crystal increases with the increase of temperature, indicating that the increase of temperature is conducive to the growth of crystal planes. The aspect ratio decreases with the increase of temperature and the morphology of cocrystal becomes more spherical. The theoretical predictions are in good agreement with the experiment.The simulation results can provide guidance for the crystallization of CL-20/1,4-DNI to obtain a nearly spherical crystal morphology.

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Synthesis of 1‐Amino‐2,4‐Dinitroimidazole Optimized by Online Infrared Spectroscopy and its Energetic Properties

Cited by 5 publications

References 24 publications

High Energy Explosive with Low Sensitivity: A New Energetic Cocrystal Based on CL-20 and 1,4-DNI

High Energy Explosive with Low Sensitivity: A New Energetic Cocrystal Based on CL-20 and 1,4-DNI

The Preparation and Properties of Submicrometer‐Sized N‐Amino‐2,4‐dinitroimidazole (ADNI): A Novel and Promising Initiating Explosive for Applications in Short Pulse Initiation Slapper Detonators

Crystal morphology prediction of CL-20 and 1,4-DNI co-crystal at different temperatures

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