Synthetic Studies of 2,6‐Diamino‐3,5‐Dinitropyrazine‐ 1‐Oxide (LLM‐105) from Discovery to Multi‐Kilogram Scale

Pagoria, Philip F.; Zhang, Maoxi; Zuckerman, Nathaniel B.; Lee, Gregory; Mitchell, Alexander R.; DeHope, Alan; Gash, Alexander E.; Coon, Clifford L.; Gallagher, Patrick

doi:10.1002/prep.201700182

Cited by 40 publications

(32 citation statements)

References 54 publications

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“…LLM‐105, as synthesized by Lawrence Livermore National Laboratory in 1995, is known as a potential insensitive high explosive (IHE) which has good prospects for application in insensitive munitions (IM) or boosters . It has a nice safety performance and 15 % higher energy than 1, 3, 5‐triamino‐2, 4, 6‐trinitrobenzene (TATB) .…”

Section: Introductionmentioning

confidence: 99%

Effects of Crystal Quality and Morphology on the Mechanical Performance of LLM‐105 Based PBXs

Yang

Lin

Gong

et al. 2019

Propellants Explo Pyrotec

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Mechanical performance is significant for the application of pressed polymer bonded explosives (PBXs) materials. In this research, several types of 2,6‐diamino‐3,5‐dinitropyrazine‐1‐oxide (LLM‐105) were selected to study the effects of crystal quality and morphology on the mechanical performance of LLM‐105 based PBXs. The surface bonding status of the LLM‐105 crystal and molding powder was characterized by scanning electron microscopy (SEM) and contact angle analysis, and the moldability was evaluated by determining the relative density of pressed cylinders of corresponding PBXs. Besides, static and dynamic mechanical properties were studied and compared, presenting the compressive, tensile and creep curves. For LLM‐105 based PBXs, spherical morphology and rough surface could result improved mechanical strength and creep resistance, facilitating the structural and dimensional stability of charges. In this case, it can bring benefits for their reliability and safety performances during application.

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Section: Introductionmentioning

confidence: 99%

Effects of Crystal Quality and Morphology on the Mechanical Performance of LLM‐105 Based PBXs

Yang

Lin

Gong

et al. 2019

Propellants Explo Pyrotec

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“…LLM-105 is a typical high energetic and insensitive explosive, which was first described by Pagoria and coworkers in 1998 [26]. Because of its excellent thermal stability and safety, LLM-105 has potential applications in specialty munitions and civil fields [27]. As depicted in Figure 1a, the molecular structure contains nitro and amino groups, resulting in strong intermolecular and intramolecular hydrogen bonds interactions.…”

Section: Introductionmentioning

confidence: 99%

Tuning the Crystal Habits of Organic Explosives by Antisolvent Crystallization: The Case Study of 2,6-dimaino-3,5-dinitropyrazine-1-oxid (LLM-105)

et al. 2019

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Crystallization is one of the most important methods in the crystal habit control of explosive products. For this study, the antisolvent crystallization experiments were carried out to tune the crystal habits of 2,6-dimaino-3,5-dinitropyrazine-1-oxid (LLM-105). Dimethyl sulphoxide (DMSO) was used as an organic solvent. Water, methanol, acetic acid, nitromethane, acetone, ethanol, methylene chloride, o-dichlorobenzene, and toluene were selected as antisolvents. The X-shaped, spherical cluster-like, rod-like, needle-like, and dendritic crystals were successfully produced by varying the kind of the antisolvent. These results manifested that the polarity and functional groups of antisolvent molecules played important roles in the crystal habits of LLM-105 explosive. The powder X-ray diffraction (PXRD) and Fourier transform infrared (FT-IR) measurements indicated that these antisolvents just tuned the crystal habit of LLM-105 but did not change the crystal structure. The differential scanning calorimetry (DSC) and thermogravimetry (TG) results of the obtained crystals showed that the crystal habits significantly affected the thermal properties. This study can contribute to the investigation of the mechanism of antisolvent-induced crystal habit modification and screen out the efficient antisolvents.

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“…But the NMR spectrum and elemental analysis also can prove the successful synthesis of these compounds. Especially, the 19 F NMR spectrum of compound 6 is similar with that of CF 3 COOH (À 76.2 ppm), which indicates the trifluoromethyl functionalization of ANPZ can be successfully introduced through this unexpected reaction pathway.…”

Section: Full Papermentioning

confidence: 68%

“…By oxidation, its more famous derivative 2,6-diamino-3,5-dinitropyrazine-1-oxide (LLM-105) was first described by Pagoria in 1998 [16,17]. Many studies have been performed on the synthesis [18,19], molecular structure [20,21] and applications of this derivative [22,23]. However, unlike the famous FOX-7 (1,1-diamino-2,2-dinitroethylene) and its derivatives [24,25,26], the derivatives of ANPZ are rarely reported besides the LLM-105 [27,28,29], even though both of them have symmetrically two amino groups and two nitro groups in their backbone structure.…”

Section: Introductionmentioning

confidence: 99%

An Unexpected Method to Synthesize Fluorinated Derivative of ANPZ

Huang

Guo

et al. 2019

Propellants Explo Pyrotec

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Nucleophilic reaction of ANPZ (2,6-diamino-3,5-dinitropyrazine) with formaldehyde was researched for the first time to synthesize its N-hydroxymethyl derivative. With further modification, ether derivative and fluorinated derivative of ANPZ were obtained by an unexpected reaction pathway. The physical properties of new derivatives were also determined by experimental and theoretical methods, which indicate that fluorinated functionalization can be easily introduced by this unexpected method to improve the integrated performance of energetic materials.

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Synthetic Studies of 2,6‐Diamino‐3,5‐Dinitropyrazine‐ 1‐Oxide (LLM‐105) from Discovery to Multi‐Kilogram Scale

Abstract: A description of the various approaches to the synthesis of the insensitive energetic compound, 2,6-diamino-3,5-dinitropyrazine-1-oxide (LLM-105), developed at LLNL over the past 20 years will be described.

Cited by 40 publications

References 54 publications

Effects of Crystal Quality and Morphology on the Mechanical Performance of LLM‐105 Based PBXs

Effects of Crystal Quality and Morphology on the Mechanical Performance of LLM‐105 Based PBXs

Tuning the Crystal Habits of Organic Explosives by Antisolvent Crystallization: The Case Study of 2,6-dimaino-3,5-dinitropyrazine-1-oxid (LLM-105)

An Unexpected Method to Synthesize Fluorinated Derivative of ANPZ

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