From phone cases to industrial piping, polymers are utilized in a wide variety of products that see daily use. As such, the lifespan of those materials is somewhat limited, leading to the desire for more sustainable materials. Here, furan and its derivatives are investigated as potential reagents for use in thermal self-healing polymeric material. Pentafluorophenyl furyl ether and furyl butyl ether were synthesized in 24% and 6% yields respectively. Here, the kinetics and thermodynamics of the reaction of furan and its derivatives with N-(4-fluorophenyl) maleimide were comparatively studied. Through the development of improved laboratory techniques, it was determined that kinetic reactions should be allowed to proceed for 15% of the time a given reaction took to equilibrate (teq), and each reaction was monitored as it progressed using a custom 19F NMR macro. The reaction of furfuryl alcohol with N-(4-fluorophenyl) maleimide proceeded the most quickly (k’ = 3.18x10-5 s-1) and produced the largest relative amount of product at equilibrium (Go = -12.6 kJ/mol) while the reaction with pentafluorophenyl furyl ether proceeded the most slowly and with least product favorability at equilibrium (k’ = 8.15x10-7 s-1 and Go = -2.41 kJ/mol). Further, as reaction temperature increased, it was noted that all reactions occurred more quickly and that equilibrium constants for those reactions decreased. Error attributed to these values may have arisen from inaccurate measurements in terms of time scale when performing analyses on the NMR.

Modelling for polymer chemistry: Using 19F NMR to determine furan-maleimide reaction properties

2019 Spring National Meeting

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