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Title: INVESTIGATION OF A N-BUTYL-N-(2-NITROXYETHYL)NITRAMINE (BUNENA) PROCESS: IDENTIFICATION OF PROCESS INTERMEDIATES, BY-PRODUCTS AND REACTION PATHWAYS

Author
item SITZMANN, MICHAEL - NAVAL SURFACE WARFARE CTR
item TRIVEDI, NIRUPAM - NAVAL AIR WAREFARE CTR
item SKAHAN, PATRICK - NAVAL SURFACE WARFARE CTR
item Kenar, James - Jim
item NOCK, LORI - NAVAL SURFACE WARFARE CTR
item STERN, ALFRED - NAVAL SURFACE WARFARE CTR

Submitted to: Trade Journal Publication
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 7/28/2005
Publication Date: 4/18/2006
Citation: Sitzmann, M.E., Trivedi, N.J., Skahan, P.B., Kenar, J.A., Nock, L.A., Stern, A.G. 2006. Investigation of a n-butyl-n-(2-nitroxyethyl)nitramine (bunena) process: identification of process intermediates, by-products and reaction pathways. Propellants, Explosives, Pyrotechnics. 31(2):124-130.

Interpretive Summary: In the interest of developing useful propellant formulation ingredients that meet insensitive munitions requirements, an in-depth process study of an energetic plasticizer was undertaken. This work provides fundamental information about reaction pathways, potential intermediates, by-products, and decomposition products formed during plasticizer synthesis which is not currently available to the international community. The basic knowledge gained from this research has clear importance for the potential applications for the use of the energetic plasticizer studied.

Technical Abstract: A process for N-butyl-N-(2-nitroxyethyl)nitramine (BuNENA) was investigated: Step 1 involves N-butyl-ethanolamine addition to 98% HNO3 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.