Synthesis of Nitroesters Based on Methylol Derivatives of Parabanic and Isocyanuric Acids

Oxalyl Chloride and Hydrazide Based Energetic Polynitro Derivatives

“…of TNE. These two compounds were previously briefly mentioned and only insufficiently characterized , . The further reaction of 2 with 3,3,3‐trinitropropanol afforded the asymmetric ester 2,2,2‐trinitroethyl (3,3,3‐trinitropropyl) oxalate ( 3 ).…”

“…Bis(2,2,2‐trinitroethyl) Oxalate (1): Oxalyl chloride (1.0 g, 7.9 mmol) and 2,2,2‐trinitroethanol (5.7 g, 31.5 mmol) were dissolved in 1,2‐dichloroethane (10 mL), and AlCl 3 (0.1 g, 8.7 mmol) was added. The solution was heated under reflux for 5 h. After the reaction mixture cooled, a colorless solid precipitated.…”

“…2,2,2‐Trinitroethyl Chloro(oxo)acetate (2): 2,2,2‐Trinitroethanol (4.1 g, 22.6 mmol) was dissolved in diethyl ether (6 mL), and oxalyl chloride (11.8 g, 93.2 mmol) was added. The solution was heated under reflux at 50 ℃C for 12 h. The solvent was removed in vacuo, and 2 was obtained as a colorless liquid (62 %) and used without further purification.…”

“…We have synthesized a large number of compounds with these two moieties during our recent studies, but little is known about the chemistry of TNE with oxalyl chloride . This contribution gives a detailed account about this topic and related compounds.…”