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Thionyl Nitrate as Nitrating Agent for the Synthesis of 2‐[Butyl(nitro)amino]ethyl Nitrate (n‐BuNENA)
Author(s) -
Bayat Yadollah,
Esmailmarandi Fatemeh
Publication year - 2017
Publication title -
propellants, explosives, pyrotechnics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.56
H-Index - 65
eISSN - 1521-4087
pISSN - 0721-3115
DOI - 10.1002/prep.201600038
Subject(s) - nitration , nitrate , thionyl chloride , chemistry , nitro , yield (engineering) , lithium nitrate , organic chemistry , nuclear chemistry , materials science , ion , chloride , ionic bonding , metallurgy , alkyl
The synthesis of n‐BuNENA by reaction of N ‐butylethanolamine and thionyl nitrate is reported herein. Various nitrating agents were studied and thionyl nitrate was found to be a promising nitrating agent. The reaction conditions for the nitration with thionyl nitrate were optimized and the best results were obtained with one equivalent of thionyl nitrate at 0 °C for 3 h. This method has a number of advantages such as performing the reaction in one step, easy handling and work‐up, and good yield. The reaction progress was monitored by HPLC and the product was characterized by IR and 1 H NMR spectroscopy.