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The cluster of excellence “Tailor-Made Fuels from Biomass” (TMFB) at RWTH Aachen University seeks to identify and investigate new potential biofuels and their production routes. To ensure a safe handling in common-rail systems the lubricity of future biofuels is part of the investigations. To further deepen the understanding of the behaviour of such fluids in the regime of boundary lubrication a group of twelve potential biofuels and systematically derived fluids was investigated by a modified version of the standardised High Frequency Reciprocating Rig test procedure for Diesel lubricity. Insufficient lubricity is observed for most biofuels whereas linear molecules with polar head groups provide good or very good lubrication. For all studied groups longer molecules provide better lubricities. The position of the functional group significantly influences the overall lubricity and impact of the carbon chain length.