From Wikipedia, the free encyclopedia
3,3-Bis(azidomethyl)oxetane
Names
IUPAC name
3,3-bis(azidomethyl)oxetane
Identifiers
Abbreviations
BAMO
InChI=1S/C5H8N6O/c6-10-8-1-5(2-9-11-7)3-12-4-5/h1-4H2
C1C(CO1)(CN=[N+]=[N-])CN=[N+]=[N-]
Properties
C 5 H 8 N 6 O
Molar mass
168.160 g·mol−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
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]
[1]
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.
[1]
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]
References
^
a
b
c Pisharath, Sreekumar; Ang, How Ghee (2007).
"Synthesis and thermal decomposition of GAP–Poly(BAMO) copolymer" . Polymer Degradation and Stability . 92 (7): 1365–1377.
doi :
10.1016/j.polymdegradstab.2007.03.016 .
^ 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 . 14 (1): 37–44.
doi :
10.2514/2.5263 .
ISSN
0748-4658 .
^ 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 . 14 (1): 9–14.
doi :
10.1080/1539445X.2015.1089904 .
ISSN
1539-445X .
S2CID
100659161 .
^ 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.
doi :
10.14429/dsj.52.2159 .
S2CID
98035395 . Archived from
the original on 2020-09-28. Retrieved 2022-03-21 .