Synthesis and Characterization of the Monomer 2,2′ diallylbisphenol‐A (ABFA) for obtaining Proton Exchange Membranes based on Crosslinked Sulphonated Poly(Arylene ether sulphone)s

Abstract

AbstractSummary: In the present work, a methodology of synthesis and characterization of the monomer 2,2′ diallylbisphenol‐A (ABFA) was developed, aiming at getting a precursor, with adequate purity, for obtaining cross‐linked membranes based on sulphonated poly(arylene ether sulphone)s. The monomer synthesis involved the synthesis of 2,2′ bis(4‐allyloxiphenyl)propane (Bisphenol‐A, diallyl ether ‐ BFAAE), from Bisphenol‐A (BFA), followed by Claisen rearrangement of BFAAE, for the production of the target compound 2,2′ diallylbisphenol‐A (ABFA). All the compounds, reagent BFA and obtained products, intermediate product BFAAE and final product ABFA, were characterized by FTIR (Fourier Transform infrared spectroscopy), TGA (Thermo‐gravimetric analysis) and HPLC (High‐performance liquid chromatography). The compound BFAAE was obtained with a yield of 94.5% and a purity of 97.3%, the latter characterized by TGA and by HPLC. The structure of the product was confirmed by FTIR. The thermal Claisen rearrangement process was conducted by using Differential Scanning Calorimetry (DSC) technique, from a factorial experiment planning, with two factors and three levels, with temperature and time being the variables. The above cited techniques were used for monitoring the Claisen rearrangement and for the characterization of the final product. The best results yield ABFA purity between 85 and 90%, approximately, for 220 °C/60min, 230 °C/30min and 210 °C/90min conditions. The obtained results suggest that, in the studied range, polymerization and degradation of the monomer ABFA occur, simultaneously to its formation.