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The presence of a variety of chemical species related to the gaseousprecursor isoprene in ambient secondary organic aerosol (SOA) has stimulatedinvestigations of the nature of SOA-phase chemical processing. Recent workhas demonstrated that 2-methylglyceric acid (2-MG) is an importantisoprene-derived ambient SOA component and atmospheric chamber experimentshave suggested that 2-MG may exist in oligomeric form (as oligoesters) underconditions of low SOA water content. In order to better understand thethermodynamic and kinetic parameters of such oligomerization reactions,nuclear magnetic resonance techniques were used to study the bulk phaseacid-catalyzed aqueous reactions (Fischer esterification) of 2-MG. While thepresent results indicate that 2-MG oligoesters are formed in the bulk phasewith similar water content equilibrium dependences as observed inatmospheric chamber SOA experiments, the acid-catalyzed rate of the Fischeresterification mechanism may be too slow to rationalize the 2-MG oligoesterproduction timescales observed in the atmospheric chamber experiments.Furthermore, it appears that unrealistically high ambient SOA aciditieswould also be required for significant 2-MG oligoester content to arise viaFischer esterification. Therefore, the present results suggest that other,more kinetically facile, esterification mechanisms may be necessary torationalize the existence of 2-MG oligomers in atmospheric chamber-generatedand ambient SOA

Study of the kinetics and equilibria of the oligomerization reactions of 2-methylglyceric acid