Nitration of chitin monomer: From glucosamine to energetic compound

Hui Dou, Yuxuan Zheng, Manyi Qu, Peng Chen, Chunlin He, Michael Gozin, Siping Pang

Research output: Contribution to journalArticlepeer-review


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 (Vd: 7717 m·s−1; P: 25.6 GPa) to that of nitrocellulose (NC: Vd: 7456 m·s−1; P: 23 GPa; Isp = 239 s) and microcrystalline nitrocellulose (MCNC; Vd: 7683 m·s−1; P: 25 GPa; Isp = 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 (Isp: 240 s), which is comparable with NC (Isp: 239 s) and MCNC (Isp: 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.

Original languageEnglish
Article number7531
Issue number24
StatePublished - 1 Dec 2021


  • Energetic materials
  • N-acetyl-D-glucosamine
  • Nitration
  • Propellants


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