Investigation of an N‐Butyl‐N‐(2‐Nitroxyethyl)Nitramine (BuNENA) Process: Identification of Process Intermediates, By‐Products and Reaction Pathways | Zendy

Sitzmann Michael E. | Zendy; Trivedi Nirupam J. | Zendy; Skahan Patrick B. | Zendy; Kenar James A. | Zendy; Nock Lori A. | Zendy; Stern Alfred G. | Zendy

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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

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.

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