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Identification and behavior of TODGA and T(EH)DGA radiolysis products

Solutions of the diglycolamide extractants TODGA and T(EH)DGA in n‐dodecane were subjected to γ‐ irradiation in the presence and absence of an acidic aqueous phase.  These solutions were then analyzed using UHPLC‐ESI‐MS to determine the rates of radiolytic decay of the two extractants, as well as to identify radiolysis products.  The concentrations of the diglycolamide derivatives were shown to decrease in an exponential fashion with increasing dose, and the measured decay rate constants were not influenced by the presence or absence of an acidic aqueous phase, or by chemical variations in the alkyl side‐chains.  The DGA degradation was attributed to reactions of the dodecane radical cation, whose kinetics were measured for TODGA using picosecond electron pulse radiolysis to be k1 = (9.72 ± 1.10) x 10 M s.  A number of radiolysis products were identified, consistent with those previously identified for these two compounds using GC‐MS.  The identity of these radiolysis products suggests that the bonds most vulnerable to radiolytic attack are those in the diglycolamide center of these molecules, and not on the side‐chains.  The major products of these reactions retain the ability to form multidentate coordination complexes with metal cations, so radiolysis reactions may not immediately play a large role in influencing distribution ratios or separation factors.  The highly predictable degradation rates should enable direct correlation of chemical changes in the extractant systems with changes in the separation performance.