Reexamination of an Energetic Nitrate Ester SHN

Abstract

A well‐known energetic nitrate ester sorbitol hexanitrate (SHN) was synthesized and characterized. SHN was shown to exhibit the highest density at ambient temperature among all known nitrate esters synthesized from simple polyols. SHN was compared with conventional 1,4‐dinitrato‐2,3‐dinitro‐2,3‐bis(nitratomethylene)‐butane (SMX) as a component of plasticizers in compositions comprising polar synthetic polymers (polyurethane and butadiene/acrylonitrile copolymer). Solid–liquid diagrams for SHN and SMX in diethylene glycol dinitrate (DEGDN) are presented. The energy characteristics and densities of the two‐component plasticizers were shown to be higher than those of DEGDN alone.

Characterization of the Hexanitrate Esters of Sugar Alcohols

“…In 2017, Gribanov et al. reported the crystal structure of SHN along with its melting point (53 °C) and 1 H and 13 C NMR spectra [25]. Gribanov synthesized SHN using the acetyl nitrate method, a method that often produces high yields of nitrated product [33].…”

“…While MHN exclusively formed a solid when poured on ice water, SHN behavior varied; sometimes SHN formed a solid that remained suspended in the stirring ice water, and sometimes it formed an oil. This crude SHN oil was dissolved in methylene chloride, washed with water and saturated aqueous sodium bicarbonate solution, and the solvent removed under reduced pressure [25]. Crystallization of the oil from methylene chloride and hexane formed SHN (designated SHN I) that melted at 53–55 °C.…”

“…SHN did not always crystallize out when the crude reaction was poured into water. When SHN formed oily masses which hardened rather than forming a suspended solid in the water, it was recovered via a modified literature procedure [25]. The SHN was dissolved in methylene chloride and transferred to a separatory funnel where it was washed three times with water, followed by three times with saturated sodium bicarbonate solution.…”

Modifying Nitrate Ester Sensitivity Properties Using Explosive Isomers

“…NMR signals were referenced using residual solvent signals. Mannitol hexanitrate and sorbitol hexanitrate were prepared according to literature procedures. , Samples were prepared on a 2 g scale.…”

“…Nitrate esters are a common class of explosive molecules that are well-known for their straightforward synthesis procedures from the corresponding sugar molecules. Common nitrate ester explosives include pentaerythritol tetranitrate (PETN), erythritol tetranitrate (ETN), and mannitol hexanitrate (MHN), which have recently received attention in the literature due to their potential use as homemade explosives. − For example, recent reports have studied possible factors that can affect ETN stability, including particle size and physical state . However, diastereomers of ETN have not been synthesized or investigated.…”