Two new ionic liquids ([N 6,6,6,6 ][C 8:0 ] and [N 6,6,6,6 ][C 16:0 ]) synthetized from fatty acids through a salt metathesis reaction were both characterized from a physicochemical and tribological point of view. Density, viscosity, corrosion activity and thermal stability tests were performed before making tribological tests under ball-on-disc both unidirectional (with fixed and variable slide-to-roll ratio) and reciprocating configuration. The main results of this work were the following: the longer the length of the alkyl chain of the anion the lower both viscosity and density and higher both viscosity index and thermal stability; these ionic liquids (ILs) are not corrosive; the [N 6,6,6,6 ][C 16:0 ] behaved better changing from elastohydrodynamic to mixed lubrication regime at lower speeds; their antiwear behavior at high load seems depend on their viscosity (for tests made at room temperature) and thermal stability and IL-surface interaction (for tests made at high temperature).