Bis Azidomethyl Oxetane

The oxygen balance —123.66 % (calculated according to the production CO2) The nitrogen content 50 % 

Chemical and physical properties colorless liquid melting point (-78.0 °C) boiling point (67 °C) 

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The energetic nature of the azido group makes its incorporation into energetic polymers and binders very desirable. 3,3-Bis(azidomethyl)oxetane (BAMO) (28) and 3-azidomethyl-3-methyloxetane (AMMO) (33) are energetic monomers which on polymerization result in the energetic polymers poly[BAMO] (32) and Poly[AMMO] (34), respectively, both of which are under evaluation as potential energetic alternatives to HTPB in composite propellant formulations. ... 

Polymers of these compounds are in widespread use. Poly-BCMO is a very tough, durable plastic, which is estimated to have an average lifetime of 70 years in water. As most oxetanes and /3-lactones can be polymerized and copolymerized to form a variety of useful solid compositions, this application will probably grow. One unusual application mentioned is the preparation and polymerization of 3,3-bis(azidomethyl)oxetane, which could be an explosive polymer (81MI51302). 

There are a number of inert binders such as polyester, epoxy, polysulfide, polyurethane which have been reported as binders for composite propellants and plastic bonded explosives (PBXs). At present, hydroxy-terminated polybutadiene (HTPB) is regarded as the state-of-the-art workhorse binder for such applications. However, the recent trend is to use energetic binders such as poly [3,3-bis(azidomethyl oxetane)] [poly(BAMO)], poly (3-azidomethyl-3-methyl oxetane) [poly(AMMO)], PNP, GAP diol and triol, nitrated HTPB(NHTPB), poly(NiMMO), poly(GlyN) and nitrated cyclodextrin polymers poly(CDN) for PBXs and composite propellants in order to get better performance. 

Poly(trimethylene oxide) is a very regular polyether chain in a very densely packed random coil. The two C—C skeletal bonds show preference for the gauche configuration while the two C—O bonds show preference for a trans configuration. Polymers of BCMO and 3,3-bis(azidomethyl)oxetane have analogous structures, with the substituents on the central carbons oriented away from each other (77JCP(66)1901,78MI51302). 

Bis(azidomethyl)oxetane, 1896 Bis(azidothiocarbonyl) disulfide, 1012a Bis(benzeneazo) oxide, 3484 Bis(jj-benzene)chromium(0), 3505 Bis(benzene)chromium dichromate, 3845 Bis(benzenediazo) sulfide, 3485 Bis(jj-benzene)iron(0), 3506 Bis(benzeneiron)—fulvalenediyl complex, 3828 Bis(jj-benzene)molybdenum(0), 3508... 

New prepolymers based on 3,3-bis (azidomethyl) oxetane (BAMO) and 3-nitratomethyl- 3-methy-loxetane (NMMO) are used in advanced pintle-controllable solid rocket motor applications. These polymers yield favorable propellant energy with the combination of nitrato esters and ammonium nitrate, and allow solid propellant designs to compete with liquid propellants in arenas of energy management, approaching true start-stop-restart operation. 

Sanderson [2] prepared the energetic thermoplastic elastomer poly(3,3-bis (azidomethyl)-oxetane), (II), for use as a binder for a propellant, explosive, or gas generant for a supplemental restraint system in automobiles. Random block copolymers of poly(azidomethyloxirane) and poly(3,3-bis(azidomethyl)oxe-tane), (III), were also prepared by Sanderson [3] using toluene diisocyanate as the coupling agent. 

Poly(nitromethyloxirane)-b-(3,3-bis(azidomethyl)-oxetane) was also prepared. 

Nair, J.K., Reddy, T.S., Satpute, R.S., Mukundan, T., and Asthana, S.N., Synthesis and characterization of energetic thermoplastic elastomers (ETPEs) based on 3,3-bis(azidomethyl)oxetane(BAMO)-3-azi-domethyl-3-methyloxetane (AMMO) copolymers, J. Polym. Mater. 21 (2), 205, 2004. 

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