Synthesis and Characterization of 3-Difluoroaminomethyl-3-methyl Oxetane and its Homopolymer

Article Preview

Abstract:

3-Difluoroaminomethyl-3-methyl oxetane (DFAMO) was synthesized via the process of bromination, cyclization, ammonification, amino protection and fluorination with a total yield of 43% and GC purity of 96%. DFAMO was characterized by 1H, 19F, 13C nuclear magnetic resonance (NMR), fourier transform infra red (FTIR) and element analysis. The homopolymer of 3-difluoroaminomethyl-3-methyloxetane (PDFAMO), considered as energetic binder to be used in solid propellants and polymer bonded explosives, with a number-average molecular weight (Mn) about 3000 was synthesized via cationic ring-opening polymerization using boron trifluoride etherate (BTFE) as Lewis acid catalyst, 1,4-butanediol (BDO) as initiator and 1,2-dichloroethane (DCE) as aprotic solvent. The effects of BTFE/BDO feeding molar ratio and temperature of the polymerization reaction were discussed. The structure of PDFAMO was characterized by 1H and 19F NMR.

You might also be interested in these eBooks

Info:

Periodical:

Pages:

28-32

Citation:

Online since:

September 2014

Export:

Price:

Permissions CCC:

Permissions PLS:

Сopyright:

© 2014 Trans Tech Publications Ltd. All Rights Reserved

Share:

Citation:

* - Corresponding Author

[1] O. Ruff, M. Giese, Ber. Dtsch. Chem. Ges. 69 (1936) 598-603.

Google Scholar

[2] R.D. Chapman, T.G. Archibald, K. Baum, Research in energetic compounds, ADA214106. (1989).

Google Scholar

[3] R.D. Chapman, M.F. Welker, C.B. Kreutzberger, J. Org. Chem. 63 (1998) 1566-1570.

Google Scholar

[4] T. Axenrod, X.P. Guan, J. Sun, et al, Tetrahedron Lett. 42 (2001) 2621-2623.

Google Scholar

[5] G.K.S. Prakash, M. Etzkorn, G.A. Olah, et al, Chem. Commun. 42 (2002) 1712-1713.

Google Scholar

[6] R.D. Chapman, M.C. Davis, R . Gilardi, Synthetic. Commun. 33 (2003) 4173-4184.

Google Scholar

[7] R. Haiges, R. Wagner, J.A. Boatz, et al, Angew. Chem. Int. Edit. 45 (2006) 5179-5184.

Google Scholar

[8] T.G. Archibald, G.E. Manser, J.E. Immoos, U.S. Patent 5, 272, 249. (1993).

Google Scholar

[9] T.G. Archibald, G.E. Manser, J.E. Immoos, U.S. Patent 5, 420, 311. (1995).

Google Scholar

[10] A.A. Malik, G.E. Manser. T.G. Archibald, U.S. Patent 5, 650, 483. (1997).

Google Scholar