Aqua-Impregnated Resins as New Dual-Function Deuterating Agent

Abstract

This study reviews our work on novel approaches for carrying out hydrogen-deuterium (H-D) exchange reactions, culminating in a process to produce extremely pure deuterated organic compounds using solid (polymeric) reagents, e.g., cation exchangers in the deuterium form pre-swollen in deuterium oxide (D 2 O). H-D exchange reaction carried out by cation-exchange deuterating agents in a tri-phase liquid-liquid-solid systems (TMAB solution in CCl 4 -D 2 O-resin in the D-form) is accompanied by significant hydrolysis of both TMAB and TMAB-d 3 (deuterated TMAB). Substitution of the liquid aqueous phase by D 2 O taken up by the swollen resin phase eliminates the hydrolytic side-reaction. Hydrogen-deuterium exchange reaction on TMAB catalyzed by cation-exchange resins or membranes under batch or under dynamic conditions, in columns, results in 100% yield of spectroscopically pure TMAB-d 3 .