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Investigation of an N‐Butyl‐N‐(2‐Nitroxyethyl)Nitramine (BuNENA) Process: Identification of Process Intermediates, By‐Products and Reaction Pathways
Author(s) -
Sitzmann Michael E.,
Trivedi Nirupam J.,
Skahan Patrick B.,
Kenar James A.,
Nock Lori A.,
Stern Alfred G.
Publication year - 2006
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.200600018
Subject(s) - ethanolamine , acetic anhydride , salt (chemistry) , chemistry , amine gas treating , decomposition , catalysis , organic chemistry , process (computing) , nitrate , chloride , computer science , operating system
Abstract A process for N‐butyl‐N‐(2‐nitroxyethyl)nitramine (BuNENA) was investigated: Step 1 involves N‐butyl‐ethanolamine addition to 98% HNO 3 to form a salt mixture; Step 2 is addition of acetic anhydride/acetyl chloride catalyst to the salt mixture. A number of potential intermediates, by‐products, and decomposition products from this process were identified/synthesized for use as analytical standards. BuNENA process reaction pathways/mechanisms were elucidated, including the nature of the amine salt solution formed in Step 1. In addition, potential pathways that could account for by‐product formation were elaborated. A study of the consumption of acetyl nitrate in Step 2 was undertaken to prevent its build‐up.