Trinitromethyl Ethers and Other Derivatives as Superior Oxidizers

SERDP Statement of Need WPSEED-10-01 called for novel materials that can replace ammonium perchlorate (AP) as rocket motor oxidizers. The main objective of this SEED project was to develop synthetic methodology leading to any example of the chemical class of trinitromethyl ethers. There is no open-l...

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Bibliographic Details
Main Authors: Chapman, Robert D, Groshens, Thomas J, Davis, Matthew C, Lai, Wiliam W, Baldwin, Lawrence C, Hollins, Richard A, Ladd, Collin A
Format: Report
Language:English
Subjects:
AMMONIUM PERCHLORATE
CHEMICAL ANALYSIS
HEXAAZAISOWURTZITANE
MOLECULAR STRUCTURE
Organic Chemistry
OXIDIZERS
Physical Chemistry
ROCKET FUELS
Rocket Propellants
SUBSTITUTES
TRINITROETHYL
TRINITROMETHYL
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Summary:SERDP Statement of Need WPSEED-10-01 called for novel materials that can replace ammonium perchlorate (AP) as rocket motor oxidizers. The main objective of this SEED project was to develop synthetic methodology leading to any example of the chemical class of trinitromethyl ethers. There is no open-literature report of the preparation of trinitromethyl ethers, with the linkage (N02) 3C-O-C, a class of compounds that might have promise as superior oxidizers to replace ammonium perchlorate. Several attempts by us to newly prepare examples of this potentially interesting class proved unsuccessful: first, trimethylsilyl trinitromethyl ether, followed by tert-butyl trinitromethyl ether. (Nevertheless, this class of compound still appears to be a fundamentally reasonable chemical linkage.) Some other unprecedented polynitroalkane products, such as nonanitroisobutane, were briefly pursued but proved less straightforward than hoped and were abandoned. Another promising target compound pursued here was 2,6,8,12-tetranitro-4,10-bis(trinitromethyl)hexaazaisowurtzitane (DNIW, a decanitro-substituted hexaazaisowurtzitane), but synthetic strategies attempted in the course of this SEED project were unsuccessful, particularly to prepare unknown 4,10-diacetonyl-2,6,8,12- tetraacetylhexaazaisowurtzitane as a new intermediate. This target also remains of interest for pursuit outside the scope of the current project, as it has good oxygen balance and is expected to have good properties as an energetic ingredient (oxidizer or explosive). The original document contains color images.