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-2H-pyran-2,4,5-triyl trinitrate (1) was obtained. Its structure was fully characterized using infrared spectroscopy, NMR spectroscopy, elemental analysis, and X-ray diffraction. Compound 1 possesses good density (ρ: 1.721 g·cm(−3)) and has comparable detonation performance (V(d): 7717 m·s(−1); P: 25.6 GPa) to that of nitrocellulose (NC: V(d): 7456 m·s(−1); P: 23 GPa; I(sp) = 239 s) and microcrystalline nitrocellulose (MCNC; V(d): 7683 m·s(−1); P: 25 GPa; I(sp) = 250 s). However, Compound 1 has much lower impact sensitivity (IS: 15 J) than the regular nitrocellulose (NC; IS: 3.2 J) and MCNC (IS: 2.8 J). Compound 1 was calculated to exhibit a good specific impulse (I(sp): 240 s), which is comparable with NC (I(sp): 239 s) and MCNC (I(sp): 250 s). By replacing the nitrocellulose with Compound 1 in typical propellants JA2, M30, and M9, the specific impulse was improved by up to 4 s. These promising properties indicate that Compound 1 has a significant potential as an energetic component in solid propellants.