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

Johnson, Eric C.; Sabatini, Jesse J.; Chavez, David E.; Sausa, Rosario C.; Byrd, Edward F.  C.; Wingard, Leah A.; Guzmàn, Pablo E.

doi:10.1021/acs.oprd.8b00076

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:

Johnson, Eric C. ^[1];

^[1];

^[2]; Sausa, Rosario C. ^[1]; Byrd, Edward F. C. ^[1]; Wingard, Leah A. ^[1]; Guzmàn, Pablo E. ^[1]

U.S. Army Research Laboratory, Aberdeen Proving Ground, MD (United States)
Los Alamos National Lab. (LANL), Los Alamos, NM (United States)

Publication Date:: Fri May 25 00:00:00 EDT 2018

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)

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.

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                    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.  https://doi.org/10.1021/acs.oprd.8b00076

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                    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.  https://doi.org/10.1021/acs.oprd.8b00076.  https://www.osti.gov/servlets/purl/1484644.

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@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         = {Fri May 25 00:00:00 EDT 2018},

  month        = {Fri May 25 00:00:00 EDT 2018}

}

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Journal Article:

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https://doi.org/10.1021/acs.oprd.8b00076

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Cited by: 62 works

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Figures / Tables:

Figure 1: Molecular structures of bis-isoxazole-bis-methylene dinitrate (1) and bis-1,2,4-oxadiazole-bis-methylene dinitrate (2).

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Works referenced in this record:

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Works referencing / citing this record:

The High‐Pressure Characterization of Melt‐Castable Energetic Materials: 3,3′‐Bis‐Oxadiazole‐5,5′‐Bis‐Methylene Dinitrate
journal, October 2018

Bennion, Jonathan C.; Batyrev, Iskander G.; Ciezak‐Jenkins, Jennifer A.
Propellants, Explosives, Pyrotechnics, Vol. 44, Issue 2
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Tetrazolium Nitrate Anion Based Salts as Potential Melt‐Castable Explosives
journal, December 2019

Yang, Rui; Dong, Zhen; Ye, Zhiwen
ChemistrySelect, Vol. 4, Issue 48
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Efficient synthesis of N -methyltetranitropyrrole: A stable, insensitive and high energy melt-castable material
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Thaltiri, Vikranth; Chavva, Kurumurthy; Kumar, B. Sathish
New Journal of Chemistry, Vol. 43, Issue 31
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Bis(1,2,4‐oxadiazolyl) Furoxan: A Promising Melt‐Castable Eutectic Material of Low Sensitivity
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Johnson, Eric C.; Bukowski, Eric J.; Sabatini, Jesse J.
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A Family of Energetic Materials Based on 1,2,4-Oxadiazole and 1,2,5-Oxadiazole Backbones With Low Insensitivity and Good Detonation Performance
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Xue, Qi; Bi, Fu-qiang; Zhang, Jun-lin
Frontiers in Chemistry, Vol. 7
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1‐AminoTriazole Transition‐Metal Complexes as Laser‐Ignitable and Lead‐Free Primary Explosives
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Szimhardt, Norbert; Wurzenberger, Maximilian H. H.; Zeisel, Lukas
Chemistry – A European Journal, Vol. 25, Issue 8
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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

Citation Formats

Figures / Tables:

Review on Melt Cast Explosives journal, October 2011

2,4,6-Trinitrotoluene - A Useful Starting Compound in the Synthesis of Modern Energetic Compounds: 2,4,6-Trinitrotoluene - A Useful Starting Compound in the Synthesis of Modern Energetic Compounds journal, February 2018

Toxic Interactions of the Munitions Compounds TNT and RDX in F344 Rats journal, January 1990

Photolysis of nitroaromatics in aquatic systems. I. 2,4,6-trinitrotoluene journal, January 1983

Speciation of the Products of and Establishing the Role of Water in the Reaction of TNT with Hydroxide and Amines: Structure, Kinetics, and Computational Results journal, October 2013

Biological Degradation of 2,4,6-Trinitrotoluene journal, September 2001

Recent Advances in the Synthesis of High Explosive Materials journal, December 2015

A Short History Of Nitroglycerine And Nitric Oxide In Pharmacology And Physiology journal, April 2000

New plasticizers for energetic materials journal, October 2007

Synthesis, Crystal Structure, and Thermal Behaviors of 3-Nitro-1,5-bis(4,4′-dimethylazide)-1,2,3-triazolyl-3-azapentane (NDTAP) journal, February 2013

Characterization and Analysis of Tetranitrate Esters journal, February 2012

A study on the aliphatic energetic plasticizers containing nitrate ester and nitramine journal, July 2009

Synthesis and study of thermal stability of 3-nitro-1,2,4-triazole N-nitroxy-and N-azidomethyl derivatives journal, November 2009

Synthesis and properties of 5-substituted 1-dinitromethyl-3-nitro-1 H-1,2,4-triazoles journal, June 2008

Synthesis of bis-Isoxazole-bis-Methylene Dinitrate: A Potential Nitrate Plasticizer and Melt-Castable Energetic Material journal, November 2016

A Convenient and Safer Synthesis of Diaminoglyoxime journal, November 2017

One-pot synthesis of 1,2,4-oxadiazoles from carboxylic acid esters and amidoximes using potassium carbonate journal, May 2006

Improved Prediction of Heats of Formation of Energetic Materials Using Quantum Mechanical Calculations journal, January 2006

A Comparison of Methods To Predict Solid Phase Heats of Formation of Molecular Energetic Salts journal, January 2009

Accurate Predictions of Crystal Densities Using Quantum Mechanical Molecular Volumes journal, October 2007

Evaluation of electrostatic descriptors for predicting crystalline density journal, June 2013

The High‐Pressure Characterization of Melt‐Castable Energetic Materials: 3,3′‐Bis‐Oxadiazole‐5,5′‐Bis‐Methylene Dinitrate journal, October 2018

Tetrazolium Nitrate Anion Based Salts as Potential Melt‐Castable Explosives journal, December 2019

Efficient synthesis of N -methyltetranitropyrrole: A stable, insensitive and high energy melt-castable material journal, January 2019

Bis(1,2,4‐oxadiazolyl) Furoxan: A Promising Melt‐Castable Eutectic Material of Low Sensitivity journal, January 2019

A Family of Energetic Materials Based on 1,2,4-Oxadiazole and 1,2,5-Oxadiazole Backbones With Low Insensitivity and Good Detonation Performance journal, February 2020

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

Review on Melt Cast Explosives
journal, October 2011

2,4,6-Trinitrotoluene - A Useful Starting Compound in the Synthesis of Modern Energetic Compounds: 2,4,6-Trinitrotoluene - A Useful Starting Compound in the Synthesis of Modern Energetic Compounds
journal, February 2018

Toxic Interactions of the Munitions Compounds TNT and RDX in F344 Rats
journal, January 1990

Photolysis of nitroaromatics in aquatic systems. I. 2,4,6-trinitrotoluene
journal, January 1983

Speciation of the Products of and Establishing the Role of Water in the Reaction of TNT with Hydroxide and Amines: Structure, Kinetics, and Computational Results
journal, October 2013

Biological Degradation of 2,4,6-Trinitrotoluene
journal, September 2001

Recent Advances in the Synthesis of High Explosive Materials
journal, December 2015

A Short History Of Nitroglycerine And Nitric Oxide In Pharmacology And Physiology
journal, April 2000

New plasticizers for energetic materials
journal, October 2007

Synthesis, Crystal Structure, and Thermal Behaviors of 3-Nitro-1,5-bis(4,4′-dimethylazide)-1,2,3-triazolyl-3-azapentane (NDTAP)
journal, February 2013

Characterization and Analysis of Tetranitrate Esters
journal, February 2012

A study on the aliphatic energetic plasticizers containing nitrate ester and nitramine
journal, July 2009

Synthesis and study of thermal stability of 3-nitro-1,2,4-triazole N-nitroxy-and N-azidomethyl derivatives
journal, November 2009

Synthesis and properties of 5-substituted 1-dinitromethyl-3-nitro-1 H-1,2,4-triazoles
journal, June 2008

Synthesis of bis-Isoxazole-bis-Methylene Dinitrate: A Potential Nitrate Plasticizer and Melt-Castable Energetic Material
journal, November 2016

A Convenient and Safer Synthesis of Diaminoglyoxime
journal, November 2017

One-pot synthesis of 1,2,4-oxadiazoles from carboxylic acid esters and amidoximes using potassium carbonate
journal, May 2006

Improved Prediction of Heats of Formation of Energetic Materials Using Quantum Mechanical Calculations
journal, January 2006

A Comparison of Methods To Predict Solid Phase Heats of Formation of Molecular Energetic Salts
journal, January 2009

Accurate Predictions of Crystal Densities Using Quantum Mechanical Molecular Volumes
journal, October 2007

Evaluation of electrostatic descriptors for predicting crystalline density
journal, June 2013

The High‐Pressure Characterization of Melt‐Castable Energetic Materials: 3,3′‐Bis‐Oxadiazole‐5,5′‐Bis‐Methylene Dinitrate
journal, October 2018

Tetrazolium Nitrate Anion Based Salts as Potential Melt‐Castable Explosives
journal, December 2019

Efficient synthesis of N -methyltetranitropyrrole: A stable, insensitive and high energy melt-castable material
journal, January 2019

Bis(1,2,4‐oxadiazolyl) Furoxan: A Promising Melt‐Castable Eutectic Material of Low Sensitivity
journal, January 2019

A Family of Energetic Materials Based on 1,2,4-Oxadiazole and 1,2,5-Oxadiazole Backbones With Low Insensitivity and Good Detonation Performance
journal, February 2020

1‐AminoTriazole Transition‐Metal Complexes as Laser‐Ignitable and Lead‐Free Primary Explosives
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