3,3-Bis(azidomethyl)oxetane explained

3,3-Bis(azidomethyl)oxetane (BAMO) is a oxetane monomer used in energetic propellant binders and plasticizer.^{[1] [2]} It is frequently used as a copolymer to improve the physical properties of more commonly used polymers and to give them energetic properties.^[3]

Preparation

BAMO is made by reacting BCMO with sodium azide in an alkaline solution. Tetrabutyl ammonium bromide is used as a phase-transfer catalyst in the reaction.

PolyBAMO can be made by mixing boron trifluoride diethyl etherate and BAMO in trimethylolpropane. The polymerization of BAMO destroys the oxetane ring, but the azide groups remain intact.^[4]

Notes and References

1. Pisharath . Sreekumar . Ang . How Ghee . 2007 . Synthesis and thermal decomposition of GAP–Poly(BAMO) copolymer . Polymer Degradation and Stability . en . 92 . 7 . 1365–1377 . 10.1016/j.polymdegradstab.2007.03.016.
2. Lee . Young Joo . Tang . Ching-Jen . Kudva . Gautam . Litzinger . Thomas A. . 1998 . Thermal Decomposition of 3,3'-Bis-Azidomethyl-Oxetane . Journal of Propulsion and Power . en . 14 . 1 . 37–44 . 10.2514/2.5263 . 0748-4658.
3. Zhang . Chi . Li . Jie . Luo . Yunjun . Yan . Shi . 2016-01-02 . Synthesis and thermal decomposition of 3,3'-bis-azidomethyl oxetane-3-azidomethyl-3'-methyl oxetane random copolymer . Soft Materials . en . 14 . 1 . 9–14 . 10.1080/1539445X.2015.1089904 . 100659161 . 1539-445X.
4. Nair . J. K. . Satpute . R. S. . Polke . B. G. . Mukundan . T. . Asthana . S. N. . Singh . Haridwar . 2002-04-01 . Synthesis and Characterisation of Bis-azido Methyl Oxetane and its Polymer and Copolymer with Tetrahydrofuran . Defence Science Journal . 52 . 2 . 147–156 . 10.14429/dsj.52.2159 . 98035395 . 2022-03-21 . 2020-09-28 . https://web.archive.org/web/20200928150852/https://publications.drdo.gov.in/ojs/index.php/dsj/article/view/2159 . dead .