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

Solid–Liquid Phase Equilibrium and Dissolution Properties of 1,3,5,7-Tetranitro-1,3,5,7-tetraazacyclooctane Form α in Pure Organic Solvents

“…In the tested solvents, the order of solubility can be divided into the following three cases: DMSO > acetone > cyclopentanone > ethyl acetoacetate > 2-butanone > acetonitrile > pyridine > methyl propyl ketone > methyl acetate > ethyl acetate > isopropyl acetate > acetic acid before 303.15 K; DMSO > cyclopentanone > acetone > ethyl acetoacetate > 2- As of now, the published literature on the solubility data of HMX is mainly focused on β-HMX. The solubility data of α-HMX in this work was compared graphically with the reported solubility data of β-HMX in literature [21][22][23]36,37 in Figure 6. Obviously, there are differences in the literature data among different researchers, but by comparing the solubility data of α-HMX in this work with the reported solubility data of β-HMX, it was found that in the corresponding solvents (pyridine, acetic acid, cyclopentanone, acetonitrile, ethyl acetate, DMSO), the solubility of α-HMX is generally higher than that of β-HMX at the same temperature.…”

Phase Equilibrium and Thermodynamics Studies on Dissolving Processes of Energetic Compounds: A Brief Review

“…Herein, DMSO shows the strongest dissolving effect on HMX of 0.0737 mol•mol −1 at 298 K and 0.1576 mol•mol −1 at 358 K, which is almost twice that in GBL with 0.0381 mol•mol −1 at 298 K and 0.0755 mol•mol −1 at 358 K. 51 As shown in Figure 2b, at ∼298 K, the solubilities of HMX in ACE, 2-butanone, acetonitrile (ACN), pyridine, and EA are at a very low level (<0.0052 mol•mol −1 ). Even though the value increases as the temperature rises, it is still very small even at high temperature, e.g., 0.0084 mol•mol −1 in ACE at 323 K, 0.0085 mol•mol −1 in ACN at 348 K, and 0.0081 mol• mol −1 in pyridine at 358 K. 57 However, in a commonly used organic solvent EA, HMX is slightly soluble with a solubility of 0.00134 mol•mol −1 at 322.4 K and 0.00232 mol•mol −1 at 338.4 K. 58 Figure 2c shows the solubility curves of HMX in a GBL/ water binary solvent, and a significant decrease in solubility can be observed with the increase of mass fraction of water in that binary solvent. In addition to temperature, the effect of pH and particle size on its solubility has also been studied.…”

“…Varying experimental methods have been adopted to investigate the dissolution characteristics of HMX in different solvents, including the HPLC method and HPLC with UV detection, the static equilibrium method, − FBRM, , and the laser monitoring method. − The static equilibrium method has a relatively stable performance in solubility measurements, comparing the solubility in dimethyl sulfoxide (DMSO) and ACE from refs and . But there is a deviation between the solubility values obtained by different methods.…”

“…Even though the value increases as the temperature rises, it is still very small even at high temperature, e.g., 0.0084 mol·mol –1 in ACE at 323 K, 0.0085 mol·mol –1 in ACN at 348 K, and 0.0081 mol·mol –1 in pyridine at 358 K . However, in a commonly used organic solvent EA, HMX is slightly soluble with a solubility of 0.00134 mol·mol –1 at 322.4 K and 0.00232 mol·mol –1 at 338.4 K Figure c shows the solubility curves of HMX in a GBL/water binary solvent, and a significant decrease in solubility can be observed with the increase of mass fraction of water in that binary solvent.…”