Study of tropaeolin degradation by iron--proposition of a reaction mechanism

The degradation of tropaeolin by iron was studied under oxidizing and inert atmospheres. The products were identified by various chromatographic and spectroscopic methods. Under inert atmosphere, the proposed model of mechanism is based on the adsorption of tropaeolin by the sulfonate function on the solid iron, followed by a reduction of the [bond]Nz[double bond]N[bond] bond with formation of 1-amino-2-naphthol and sulfanilic acid. These two intermediaries were reduced to 1,2-dihydroxynaphthalene and benzene with NH(4)(+) and HSO(3)(-) liberation. Under oxidizing atmosphere, besides the reductions of tropaeolin, water and ferric ions, the existence of a homogeneous degradation was found. This process was explained (on the basis of surface iron potential monitoring) by a stepwise reduction of oxygen giving hydrogen peroxide. The initial stages of the mechanism were similar to those under inert atmosphere, but the degradation of the 1,2-dihydroxynaphthalene continued giving 1,2-naphthalenedione, then various polar monocyclic compounds leading to three unidentified volatile final products.