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Title: Bis(1,2,4-oxadiazole)bis(methylene) Dinitrate: A High-Energy Melt-Castable Explosive and Energetic Propellant Plasticizing Ingredient

Abstract

Here, we discuss the synthesis of bis(1,2,4-oxadiazole)bis(methylene) dinitrate, determination of its crystal structure by X-ray diffractometry, calculations of its explosive performance, and sensitivity measurements. Steps taken to optimize the synthesis process and to improve yields of the dinitrate are also discussed. Bis(1,2,4-oxadiazole)bis(methylene) dinitrate has a calculated detonation pressure 50% higher than that of TNT. The dinitrate compound exhibits a relatively high decomposition temperature that is rarely observed for nitrate-based compounds. The dinitrate was found to have lower sensitivities to impact and friction compared with RDX. Finally, it is believed that intramolecular hydrogen bonding observed in the crystal lattice assists in the relatively high thermal stability and relatively low sensitivity of the material.

Authors:
 [1]; ORCiD logo [1]; ORCiD logo [2];  [1];  [1];  [1];  [1]
  1. U.S. Army Research Laboratory, Aberdeen Proving Ground, MD (United States)
  2. Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
Publication Date:
Research Org.:
Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
Sponsoring Org.:
USDOE National Nuclear Security Administration (NNSA), Office of Defense Programs (DP) (NA-10)
OSTI Identifier:
1484644
Report Number(s):
LA-UR-18-24152
Journal ID: ISSN 1083-6160
Grant/Contract Number:  
89233218CNA000001
Resource Type:
Accepted Manuscript
Journal Name:
Organic Process Research & Development
Additional Journal Information:
Journal Volume: 22; Journal Issue: 6; Journal ID: ISSN 1083-6160
Publisher:
ACS Publications
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 36 MATERIALS SCIENCE

Citation Formats

Johnson, Eric C., Sabatini, Jesse J., Chavez, David E., Sausa, Rosario C., Byrd, Edward F. C., Wingard, Leah A., and Guzmàn, Pablo E. Bis(1,2,4-oxadiazole)bis(methylene) Dinitrate: A High-Energy Melt-Castable Explosive and Energetic Propellant Plasticizing Ingredient. United States: N. p., 2018. Web. doi:10.1021/acs.oprd.8b00076.
Johnson, Eric C., Sabatini, Jesse J., Chavez, David E., Sausa, Rosario C., Byrd, Edward F. C., Wingard, Leah A., & Guzmàn, Pablo E. Bis(1,2,4-oxadiazole)bis(methylene) Dinitrate: A High-Energy Melt-Castable Explosive and Energetic Propellant Plasticizing Ingredient. United States. doi:10.1021/acs.oprd.8b00076.
Johnson, Eric C., Sabatini, Jesse J., Chavez, David E., Sausa, Rosario C., Byrd, Edward F. C., Wingard, Leah A., and Guzmàn, Pablo E. Fri . "Bis(1,2,4-oxadiazole)bis(methylene) Dinitrate: A High-Energy Melt-Castable Explosive and Energetic Propellant Plasticizing Ingredient". United States. doi:10.1021/acs.oprd.8b00076. https://www.osti.gov/servlets/purl/1484644.
@article{osti_1484644,
title = {Bis(1,2,4-oxadiazole)bis(methylene) Dinitrate: A High-Energy Melt-Castable Explosive and Energetic Propellant Plasticizing Ingredient},
author = {Johnson, Eric C. and Sabatini, Jesse J. and Chavez, David E. and Sausa, Rosario C. and Byrd, Edward F. C. and Wingard, Leah A. and Guzmàn, Pablo E.},
abstractNote = {Here, we discuss the synthesis of bis(1,2,4-oxadiazole)bis(methylene) dinitrate, determination of its crystal structure by X-ray diffractometry, calculations of its explosive performance, and sensitivity measurements. Steps taken to optimize the synthesis process and to improve yields of the dinitrate are also discussed. Bis(1,2,4-oxadiazole)bis(methylene) dinitrate has a calculated detonation pressure 50% higher than that of TNT. The dinitrate compound exhibits a relatively high decomposition temperature that is rarely observed for nitrate-based compounds. The dinitrate was found to have lower sensitivities to impact and friction compared with RDX. Finally, it is believed that intramolecular hydrogen bonding observed in the crystal lattice assists in the relatively high thermal stability and relatively low sensitivity of the material.},
doi = {10.1021/acs.oprd.8b00076},
journal = {Organic Process Research & Development},
number = 6,
volume = 22,
place = {United States},
year = {2018},
month = {5}
}

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Works referencing / citing this record:

CCDC 1819160: Experimental Crystal Structure Determination: CIGSUJ : ((3,3'-bi-1,2,4-oxadiazole)-5,5'-diyl)bis(methylene) dinitrate
dataset, January 2018


1‐AminoTriazole Transition‐Metal Complexes as Laser‐Ignitable and Lead‐Free Primary Explosives
journal, October 2018

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