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A Halogen‐Free Green High Energy Density Oxidizer from H‐FOX
Author(s) -
Dharavath Srinivas,
Tang Yongxing,
Kumar Dheeraj,
Mitchell Lauren A.,
Parrish Damon A.,
Shreeve Jean'ne M.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900415
Subject(s) - chemistry , ammonium perchlorate , yield (engineering) , derivative (finance) , detonation , medicinal chemistry , nitric acid , halogen , acetic acid , nitro , nuclear chemistry , inorganic chemistry , organic chemistry , explosive material , catalysis , materials science , alkyl , financial economics , metallurgy , economics
Reaction of H‐FOX (1‐hydrazinyl‐2,2‐dinitroethenamine) with 2,2,2‐trinitroethanol resulted in an unexpected compound, 1,1′‐methylenebis[3‐(2,2,2‐trinitroethyl)urea] ( 5 ), which when treated with acetic anhydride and 100 % nitric acid gave an N ‐NO 2 derivative, 1,1′‐methylenebis[1‐nitro‐3‐(2,2,2‐trinitroethyl)urea] ( 6 ) in good yield. Compound 6 exhibits a good oxygen balance (+20.4 %), density ( d = 1.87 g/cm 3 ) and excellent detonation performance (vD = 8910 m/s; P = 35.8 GPa) as well as acceptable stability and sensitivity, which suggests it as an attractive replacement for ammonium perchlorate (AP).