A Solubility Comparison of Cyclotetramethylenetetranitramine (HMX) and Potential Mock-HMX Candidates in Solvents Relevant to Slurry Formulating Polymer-Bonded Materials

Bowden, Patrick Robert; Shorty, Marvin; Yeager, John David; Duque, Amanda Lynn; Freye, Chris E.

doi:10.1007/s10953-020-00980-6

Title: A Solubility Comparison of Cyclotetramethylenetetranitramine (HMX) and Potential Mock-HMX Candidates in Solvents Relevant to Slurry Formulating Polymer-Bonded Materials

Abstract

Understanding solubility behavior of organic crystalline materials is critical in the development of slurry-formulated plastic bonded composites. In the field of high explosives (HE), a common method for obtaining high density, greater than 95 % theoretical maximum density, is to encapsulate HE in a polymer matrix resulting in the formation of plastic bonded explosive (PBX) prills. Prill formation is highly nuanced and requires understanding of particle size distributions, solvent, antisolvent, and binder system as well as interactions thereof. In this paper, in an effort to create mock-HE that mimics HE in density and mechanical strength, solubility of candidate molecules was compared to cyclotetramethylenetetranitramine (HMX) in binder solvents relevant to prill formation. The results indicate that the mock candidates chosen for this study have different solubilities compared to HMX in water and both organic solvents, 2-butanone and ethyl acetate, investigated. With these solubility differences known, prills to match PBXs based on HMX can be formulated, pressed and tested.

Authors:

^[1]; Shorty, Marvin ^[1];

^[1];

^[1]; Freye, Chris E. ^[1]

Los Alamos National Lab. (LANL), Los Alamos, NM (United States)

Publication Date:: Mon Jul 20 00:00:00 EDT 2020

Research Org.:: Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)

Sponsoring Org.:: USDOE National Nuclear Security Administration (NNSA)

OSTI Identifier:: 1663184

Report Number(s):: LA-UR-18-24379
Journal ID: ISSN 0095-9782

Grant/Contract Number:: 89233218CNA000001

Resource Type:: Accepted Manuscript

Journal Name:: Journal of Solution Chemistry

Additional Journal Information:: Journal Volume: 49; Journal Issue: 7-8; Journal ID: ISSN 0095-9782

Publisher:: Springer

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Cyclotetramethylenetetranitramine; HMX; solubility; Mock HE

Citation Formats


                    Bowden, Patrick Robert, Shorty, Marvin, Yeager, John David, Duque, Amanda Lynn, and Freye, Chris E. A Solubility Comparison of Cyclotetramethylenetetranitramine (HMX) and Potential Mock-HMX Candidates in Solvents Relevant to Slurry Formulating Polymer-Bonded Materials.  United States: N. p., 2020. 
Web.  doi:10.1007/s10953-020-00980-6.

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                    Bowden, Patrick Robert, Shorty, Marvin, Yeager, John David, Duque, Amanda Lynn, & Freye, Chris E. A Solubility Comparison of Cyclotetramethylenetetranitramine (HMX) and Potential Mock-HMX Candidates in Solvents Relevant to Slurry Formulating Polymer-Bonded Materials.  United States.  https://doi.org/10.1007/s10953-020-00980-6

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                    Bowden, Patrick Robert, Shorty, Marvin, Yeager, John David, Duque, Amanda Lynn, and Freye, Chris E. Mon .  
"A Solubility Comparison of Cyclotetramethylenetetranitramine (HMX) and Potential Mock-HMX Candidates in Solvents Relevant to Slurry Formulating Polymer-Bonded Materials".  United States.  https://doi.org/10.1007/s10953-020-00980-6.  https://www.osti.gov/servlets/purl/1663184.

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@article{osti_1663184,

  title        = {A Solubility Comparison of Cyclotetramethylenetetranitramine (HMX) and Potential Mock-HMX Candidates in Solvents Relevant to Slurry Formulating Polymer-Bonded Materials},

  author       = {Bowden, Patrick Robert and Shorty, Marvin and Yeager, John David and Duque, Amanda Lynn and Freye, Chris E.},

  abstractNote = {Understanding solubility behavior of organic crystalline materials is critical in the development of slurry-formulated plastic bonded composites. In the field of high explosives (HE), a common method for obtaining high density, greater than 95 % theoretical maximum density, is to encapsulate HE in a polymer matrix resulting in the formation of plastic bonded explosive (PBX) prills. Prill formation is highly nuanced and requires understanding of particle size distributions, solvent, antisolvent, and binder system as well as interactions thereof. In this paper, in an effort to create mock-HE that mimics HE in density and mechanical strength, solubility of candidate molecules was compared to cyclotetramethylenetetranitramine (HMX) in binder solvents relevant to prill formation. The results indicate that the mock candidates chosen for this study have different solubilities compared to HMX in water and both organic solvents, 2-butanone and ethyl acetate, investigated. With these solubility differences known, prills to match PBXs based on HMX can be formulated, pressed and tested.},

  doi          = {10.1007/s10953-020-00980-6},

  journal      = {Journal of Solution Chemistry},

  number       = 7-8,

  volume       = 49,

  place        = {United States},

  year         = {Mon Jul 20 00:00:00 EDT 2020},

  month        = {Mon Jul 20 00:00:00 EDT 2020}

}

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Works referenced in this record:

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Sitzmann, Michael E.; Foti, Stephen C.
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On the nucleation mechanism of the β-δ phase transition in the energetic nitramine octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine
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Smilowitz, L.; Henson, B. F.; Greenfield, M.
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Physico-chemical measurements of CL-20 for environmental applications
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Monteil-Rivera, Fanny; Paquet, Louise; Deschamps, Stéphane
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Quasi–static studies of the deformation and failure of β –HMX based polymer bonded explosives
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Propellants, Explosives, Pyrotechnics, Vol. 33, Issue 1
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Statistical Optimization and Selective Separation of RDX and HMX Explosives by Using Binary Solvent Mixtures Containing Ethyl Acetate and Water
journal, January 2017

Damiri, sajjad; Pouretedal, Hamid Reza; Panahi, Hadi
Central European Journal of Energetic Materials, Vol. 14, Issue 2
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Development of inert density mock materials for HMX
journal, September 2017

Yeager, John D.; Higginbotham Duque, Amanda L.; Shorty, Marvin
Journal of Energetic Materials, Vol. 36, Issue 3
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Similar Records

Title: A Solubility Comparison of Cyclotetramethylenetetranitramine (HMX) and Potential Mock-HMX Candidates in Solvents Relevant to Slurry Formulating Polymer-Bonded Materials

Abstract

Citation Formats

Solubilities of explosives. Dimethylformamide as general solvent for explosives journal, January 1975

Crystallization of HMX from γ-butyrolactone journal, February 1986

Low strain rate compression measurements of PBXN-9, PBX 9501, and mock 9501 conference, January 1998

On the nucleation mechanism of the β-δ phase transition in the energetic nitramine octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine journal, September 2004

Physico-chemical measurements of CL-20 for environmental applications journal, January 2004

Quasi–static studies of the deformation and failure of β –HMX based polymer bonded explosives journal, March 2002

Nanoindentation of explosive polymer composites to simulate deformation and failure journal, October 2012

Predicting Solubility of Military, Homemade, and Green Explosives in Pure and Saline Water using COSMO-RS journal, November 2013

Pharmacokinetics of topically applied ophthalmic drugs journal, January 1982

Crystallization of Insensitive HMX journal, February 2008

Statistical Optimization and Selective Separation of RDX and HMX Explosives by Using Binary Solvent Mixtures Containing Ethyl Acetate and Water journal, January 2017

Partial Phase Behavior of HMX/DMSO Solutions journal, October 1999

Development of inert density mock materials for HMX journal, September 2017

Molecular Dynamics Investigation of Adhesion between TATB Surfaces and Amorphous Fluoropolymers journal, May 2007

Examination of Morphological Changes that Affect Gas Permeation through Thermally Damaged Explosives journal, October 2004

Thin-layer chromatographic analysis of HMX in water journal, November 1973

LASL Explosive Property Data book, December 1980

Solubilities of explosives. Dimethylformamide as general solvent for explosives
journal, January 1975

Crystallization of HMX from γ-butyrolactone
journal, February 1986

Low strain rate compression measurements of PBXN-9, PBX 9501, and mock 9501
conference, January 1998

On the nucleation mechanism of the β-δ phase transition in the energetic nitramine octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine
journal, September 2004

Physico-chemical measurements of CL-20 for environmental applications
journal, January 2004

Quasi–static studies of the deformation and failure of β –HMX based polymer bonded explosives
journal, March 2002

Nanoindentation of explosive polymer composites to simulate deformation and failure
journal, October 2012

Predicting Solubility of Military, Homemade, and Green Explosives in Pure and Saline Water using COSMO-RS
journal, November 2013

Pharmacokinetics of topically applied ophthalmic drugs
journal, January 1982

Crystallization of Insensitive HMX
journal, February 2008

Statistical Optimization and Selective Separation of RDX and HMX Explosives by Using Binary Solvent Mixtures Containing Ethyl Acetate and Water
journal, January 2017

Partial Phase Behavior of HMX/DMSO Solutions
journal, October 1999

Development of inert density mock materials for HMX
journal, September 2017

Molecular Dynamics Investigation of Adhesion between TATB Surfaces and Amorphous Fluoropolymers
journal, May 2007

Examination of Morphological Changes that Affect Gas Permeation through Thermally Damaged Explosives
journal, October 2004

Thin-layer chromatographic analysis of HMX in water
journal, November 1973

LASL Explosive Property Data
book, December 1980