Nitration of Chitin Monomer: From Glucosamine to Energetic Compound.

The nitration of chitin monomer in a mixture of nitric acid and acetic anhydride was conducted and a highly nitrated (3R,4R,6R)-3-acetamido-6-((nitrooxy)methyl)tetrahydro-2-pyran-2,4,5-triyl trinitrate () was obtained. Its structure was fully characterized using infrared spectroscopy, NMR spectroscopy, elemental analysis, and X-ray diffraction. Compound possesses good density (ρ: 1.721 g·cm) and has comparable detonation performance (V: 7717 m·s; P: 25.6 GPa) to that of nitrocellulose (NC: V: 7456 m·s; P: 23 GPa; I = 239 s) and microcrystalline nitrocellulose (MCNC; V: 7683 m·s; P: 25 GPa; I = 250 s). However, Compound has much lower impact sensitivity (IS: 15 J) than the regular nitrocellulose (NC; IS: 3.2 J) and MCNC (IS: 2.8 J). Compound was calculated to exhibit a good specific impulse (I: 240 s), which is comparable with NC (I: 239 s) and MCNC (I: 250 s). By replacing the nitrocellulose with Compound in typical propellants JA2, M30, and M9, the specific impulse was improved by up to 4 s. These promising properties indicate that Compound has a significant potential as an energetic component in solid propellants.