(568u) An Iterative Three-Stage Process for Generating Imidazolium Catalysts from Formaldehyde

Iterative processes that use feedback loops are commonplace in biology. These processes provide a mechanism for organisms to grow and adapt that is important under transient environmental conditions.On the early Earth such processes would have needed to arise spontaneously from available resources; here a model chemical process is shown to produce imidazolium ions that feedback into the process as catalysts for a reaction step.  The process can be sub-divided into three stages: two batch reactions (R1 & R2) and one chromatographic separation (S1). Stage R1 converts formaldehyde to a mixture of sugars (C_nH_2nO_n) via an imidazolium catalyzed polarity reversal. Stage R2 takes the product mixture from R1 and adds aniline to produce new imidazolium catalyst in 0.5% overall yield. Side products generated in R2 decrease reaction efficiency and inhibit catalyst activity. Stage S1 purifies the imidazolium catalysts, allowing them to be recycled back into the process. Over multiple process iterations, the population of imidazolium ions gradually changes with time; however, activity to catalyze sugar formation in stage R1 is retained. This model process based on the formation and sequestration of stable, small molecule organo-catalysts may provide an alternative to template replication in establishing systems chemistry approaches to the origins of life.