Interfacial synthesis of bisphenol A tetrachlorocyclotriphosphazene from bisphenol A and hexachlorocyclotriphosphazene

• Published in: Tetrahedron letters 2013-09, Vol.54 (39), p.5311-5313
• Main Authors: Thompson, Tiffany N., Ramos-Hunter, Susan, Robertson, Jasmine, Arnett, Natalie Y.
• Format: Article
• Language: English
• Subjects: Bisphenol A; Distillation; Hexachlorocyclotriphosphazene; Interfacial synthesis; Monomers; Nuclear magnetic resonance; Phosphonitrilic chloride trimer; Poly(arylene ether sulfone); Proton exchange membrane; Purity; Solvents; Synthesis (chemistry); Toluene
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2013.07.098

The effect of solvent purity on the synthesis and yield of bisphenol A tetrachlorocyclotriphosphazene (BATCCP) has not been described in the literature. The purpose of this research was to synthesize BATCCP hybrid monomers and to evaluate the effect of solvent purity on the BATCCP production. BATCCP monomers were prepared by an interfacial procedure in a water/toluene system as a function of time with the assistance of a phase transfer catalyst, tetraoctylammonium bromide. 1H and 31P NMR confirmed the production of BATCCP monomer by the appearance of chemical shifts at 7.18 and 5.35ppm in the 1H NMR and 23.4 and 13.9ppm in the 31P NMR, respectively. Distillation of the toluene, not suggested in previous reports of HCCP hybrid synthesis, resulted in an improvement of actual % yield to 40% and stability of the product throughout the 1440min reaction as confirmed by MALDI, compared with an 11% actual yield at 15min, decaying to 2% over a 1440min reaction when the synthesis was performed with ‘anhydrous toluene’ as provided commercially without further distillation.