Nitration of Chitin Monomer: From Glucosamine to Energetic Compound

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

doi:10.3390/molecules26247531

Molecules (Dec 2021)

Nitration of Chitin Monomer: From Glucosamine to Energetic Compound

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

Affiliations

Hui Dou: Experimental Center of Advanced Materials, School of Materials Science and Engineering, Beijing Institute of Technology, Beijing 100081, China
Yuxuan Zheng: State Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, Beijing 100081, China
Manyi Qu: Shanxi North Xingan Chemical Industry Co., Ltd., Taiyuan 030008, China
Peng Chen: Experimental Center of Advanced Materials, School of Materials Science and Engineering, Beijing Institute of Technology, Beijing 100081, China
Chunlin He: Experimental Center of Advanced Materials, School of Materials Science and Engineering, Beijing Institute of Technology, Beijing 100081, China
Michael Gozin: School of Chemistry, Faculty of Exact Sciences, Tel Aviv University, Tel Aviv 6997801, Israel
Siping Pang: Experimental Center of Advanced Materials, School of Materials Science and Engineering, Beijing Institute of Technology, Beijing 100081, China

DOI: https://doi.org/10.3390/molecules26247531
Journal volume & issue: Vol. 26, no. 24
p. 7531

Abstract

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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.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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