Reactivity of (Vicinal) Carbonyl Compounds with Urea.

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ID: 22932
2019
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Abstract
Urea removal from dialysate is the major obstacle in realization of a miniature dialysis device, based on continuous dialysate regeneration in a closed loop, used for the treatment of patients suffering from end-stage kidney disease. For the development of a polymeric urea sorbent, capable of removing urea from dialysate with high binding capacities and fast reaction kinetics, a systematic kinetic study was performed on the reactivity of urea with a library of low-molecular-weight carbonyl compounds in phosphate-buffered saline (pH 7.4) at 323 K. It was found that dialdehydes do not react with urea under these conditions but need to be activated under acidic conditions and require aldehyde groups in close proximity to each other to allow a reaction with urea. Among the 31 (hydrated) carbonyl compounds tested, triformylmethane, ninhydrin, and phenylglyoxaldehyde were the most reactive ones with urea. This is attributed to the low dehydration energies of these compounds, as calculated by Gibbs free energy differences between the hydrated and dehydrated carbonyl compounds, which are favorable for the reaction with urea. Therefore, future urea sorbents should contain such functional groups at the highest possible density.
Reference Key
jong2019reactivityacs Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Jong, Jacobus A W;Smakman, Robert;Moret, Marc-Etienne;Verhaar, Marianne C;Hennink, Wim E;Gerritsen, Karin G F;Van Nostrum, Cornelus F;
Journal ACS omega
Year 2019
DOI
10.1021/acsomega.9b01177
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