3,3-Bis(chloromethyl)oxetane explained

3,3-Bis(chloromethyl)oxetane (BCMO) is an intermediate in the synthesis of poly(bis(azidomethyl)oxetane (PolyBAMO), an energetic polymer that is being studied for use as a propellant binder for rocket fuel.^[1]

It is classified as an extremely hazardous substance in the United States.^[2] It can cause kidney damage, lacrimation, and somnolence if consumed.

Preparation and reaction

BCMO is formed in solution via cyclization of pentaerythritol trichlorohydrin with a non-organic base like sodium hydroxide.^[3]

BAMO can be formed from a reaction of BCMO with sodium azide. This reaction takes place in an alkaline solution with tetrabutyl ammonium bromide, which acts as a phrase transfer catalyst.

Notes and References

2
Web site: . 40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities . July 1, 2008 . October 29, 2011 . https://web.archive.org/web/20120225051612/http://edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf . February 25, 2012 . dead .
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.