Simple Green Synthesis and Electrochemical Performance of a New Fluorinated Carbonate as Additive for Lithium-Ion Batteries

A fluorinated carbonate (4-(2,2,3,3,4,4,5,5,5-nonafluoro-pentyl)-1,3-dioxolan-2-one, 1) was synthesized from the corresponding oxirane through a one-step carbonation reaction. The compound was obtained in quantitative yield with battery-grade purity on a 50g scale. Carbonate 1 was fully characterized by NMR, IR, MS, and crystal structure analysis. The compound melts at 98 degrees C and decomposes at 168 degrees C. When used as additive in lithium-ion half- and full-cell tests, 1 exhibited no reactivity toward the graphite anode, no participation in the solid-electrolyte interphase (SEI) formation and led to a higher oxidation stability of the electrolyte against a carbon black electrode, compared to 4-fluoro-ethylenecarbonate and 4-trifluoromethyl-1,3-dioxolan-2-one. The facile, clean, and scalable one-step synthesis of 1 combined with its electrochemical behavior characterizes it as a promising additive for high voltage applications in lithium-ion batteries.