In this paper, the soot-NOx trade-off and fuel efficiency of various aromatic oxygenates is investigated in a modern DAF heavy-duty diesel engine. All oxygenates were blended to diesel fuel such that the blend oxygen concentration was 2.59 wt.-%. The oxygenates in question, anisole, benzyl alcohol and 2-phenyl ethanol, have similar heating values and cetane numbers, but differ in the position of the functional oxygen group relative to the aromatic ring. The motivation for this study is that in lignin, a widely available and low-cost biomass feedstock, similar aromatic structures are found with varying position of the oxygen group to the aromatic ring. From the results it becomes clear that both the soot-NOx trade-off and the volumetric fuel economy (i.e. ml/kWh) is improved for all oxygenates in all investigated work points. In general, the improvement in the soot-NOx trade-off correlated with the position of the functional oxygen group to the ring, with better overall emission behavior observed as the oxygen group was further from the ring. No distinct trend was observed with respect to fuel economy.