Synthesis of Aziridine Bonding Agent HX-752 and its Imide Derivatives

Document Type : Research Article

Authors

1 Department of Chemistry, Faculty of Basic Sciences, Imam Hossein University, Tehran, I.R. IRAN

2 University Complex of Chemistry and Chemical Engineering, Malek Ashtar University of Technology, Tehran, I.R. IRAN

Abstract

One of the most important required additives in the production of composite solid propellants are bonding agents. These compounds are used in order to increase the adhesion between the polymer resin and the oxidizer and also to enhance the physical and mechanical properties and to improve the solids loading of propellants. In this research, in which the main goal was the synthesis of the bonding agent HX-752, the key intermediate, 2-methyl aziridine, was first synthesized from 1-amino-2-propanol with 51% yield by a new method.. The other intermediate, isophthalic chloride, was prepared from isophthalic acid using thionyl chloride as chlorinating agent. The desired product, 1,1'-isophthaloyl-bis(2-methylaziridine), HX-752, was finally synthesized by the reaction of isophthaloyl chloride with 2-methyl aziridine with 93% yield. In continuation of this work, MAPO (tris(2-metyl aziridine)phosphine oxide) was prepared from the reaction of 2-metylaziridine with phosphoryl chloride (POCl3) with 80% yield. Using piperidine and diethylamine, instead of 2-metylaziridine, the other fiveBonding agents similar to HX-752 and MAPO were also synthesized with appropriate yields. Characterization of the synthesized intermediates and products was performed by 1HNMR, 13CNMR, 31P-NMR spectroscopy and physical tests such as melting points for known compounds.

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References

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