Characterization of the Hexanitrate Esters of Sugar Alcohols

Abstract

The hexanitrates of the six‐carbon sugars mannitol and sorbitol were prepared and studied to gain insight in their relative stabilities. Synthesis and characterization of these materials resulted in the identification of two new crystalline polymorphs, one for each hexanitrate. Mannitol hexanitrate (MHN) exposed to elevated temperatures exhibited a different structure when measured by x‐ray diffraction (XRD) and Raman spectroscopy; however, no differences were observed in the thermal behavior. Sorbitol hexanitrate (SHN) has two distinct crystalline polymorphs that result in different melting behavior and differences in Raman and XRD. Thermal stability of these hexanitrates was also examined; despite being isomers, SHN and MHN differ in their long‐term thermal stability.

Chemical Evaluation and Performance Characterization of Pentaerythritol Tetranitrate (PETN) under Melt Conditions

“…Explosives with nitrate ester groups are commonly used in commercial, medicinal, and synthetic chemistry applications and have been studied extensively for their properties. Recently, our lab and others have explored the chemical characteristics, thermal stability, and melting point behavior of a variety of nitrate esters, such as pentaerythritol tetranitrate (PETN), erythritol tetranitrate (ETN), and mannitol hexanitrate (MHN). − PETN has been shown to melt at 141 °C, followed by an onset of decomposition of the explosive at approximately 160 °C. Due to the close proximity of the melt and the decomposition onset, few studies have been conducted on PETN in the molten state.…”