Scale up of 2,6-Diamino-3,5-Dinitropyrazine-1-Oxide (LLM-105) and Its Precusors

The Naval Surface Warfare Center at Indian Head (IHDIV, NSWC) has recently produced multi-kilogram quantities of 2,6-diamino-3,5-dinitropyrazine-1-oxide (LLM-105) at the 100-gallon scale. First synthesized by Dr. Phil Pagoria at Lawrence Livermore National Laboratory, LLM-105 is being investigated as an energetic ingredient for military applications because of its unique combination of high-density, excellent performance, thermal stability, and insensitivity. Specifically LLM-105 is being investigated as an alternative to triaminotrinitrobenzene (TATB) in several DOD and DOE military applications.

The LLM-105 reaction sequence had been developed, resulting from a three year process development and scale-up endeavor. The current three-step reaction sequence involves the nitration of 2,6-dimethoxypyrazine (DMP) to form 2,6-dimethoxy-3, 5-dinitropyrazine (DMDP), which undergoes a subsequent amination to form 2,6-diamino-3,5-dinitropyrazine (ANPZ). The third and final step involves the oxidation of ANPZ to yield the product LLM-105. IHDIV, NSWC has established a robust scale-up methodology that can be implemented in further scale-up efforts and future production campaigns. The challenges encountered during the LLM-105 development and scale-up, paired with the scientific approach used to overcome each engineering challenge, are presented.