Reaction of beta-aminoamides with aromatic aldehydes

The American Oil Chemists’ Society official methods TF 1b‐64 and TF 2b‐64, “Quantitative Determination of Amines,” fail to correctly analyze fatty diethylenetriamine (DETA)‐diamides and diamides of 3,3′’‐iminobispropylamine (DPTA). Primary amine determination through the formation of Schiff base adducts using salicylaldehyde will, in the case of secondary amines that bear amide carbonyl at either the β or γ position, undergo reactions that consume salicyladehyde despite the absence of primary amine groups. The product of this reaction has been investigated, and a cyclic (2‐arylimidazolidine) structure is advanced as the principal adduct of the reaction of aryl aldehydes with DETA‐diamides.