A Solubility Comparison of Cyclotetramethylenetetranitramine (HMX) and Potential Mock-HMX Candidates in Solvents Relevan

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A Solubility Comparison of Cyclotetramethylenetetranitramine (HMX) and Potential Mock‑HMX Candidates in Solvents Relevant to Slurry Formulating Polymer‑Bonded Materials Patrick R. Bowden1   · Marvin Shorty1 · John D. Yeager1 · Amanda L. Duque1 · Chris E. Freye1 Received: 16 November 2018 / Accepted: 2 January 2020 © This is a U.S. Government work and not under copyright protection in the US; foreign copyright protection may apply. 2020

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  which can then be pressed to high density parts. Prill formation is highly nuanced and requires understanding of particle size distributions, solvent, antisolvent, and binder system as well as interactions thereof. 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. Keywords  Cyclotetramethylenetetranitramine · HMX · Solubility · Mock HE

1 Introduction Progress is currently being made to produce mock high explosive (HE) materials that exhibit substantially similar characteristics to actual HEs for various testing scenarios. Existing mock HEs typically do a reasonable job at matching one particular attribute, but fail at others; for example, the barium nitrate-based Mock 900-21 matches the physical density of Plastic-Bonded eXplosive (PBX) 9501 but does not mimic the thermomechanical behavior well  [1]. Historically, PBXs containing cyclotetramethylenetetranitramine

* Patrick R. Bowden [email protected] 1



Los Alamos National Laboratory, Los Alamos, NM 87545, USA

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Journal of Solution Chemistry

(HMX) have been the most common targets for development and application of mock materials, but no existing mock succeeds at mimicking multiple PBX properties. Recently, an applied search for inert density mock candidates for HMX yielded three promising materials [2]. These candidates are 5-iodo-2′-deoxyuridine (IDOX), N,Nˊ-bis(2,3,4,5,6pentafluorophenyl)oxamide (N-BPFPO), and 2,3,4,5,6-pentafluorobenzamide (PFBA). In that work, the focus was on mimicking HMX thermal stability and non-detonative constitutive properties. Substituting any of these candidates one-to-one for HMX, while using the same binder as the real PBX, was hypothesized to be a suitable approach for developing a new mock material. Figure 1 shows th