154917-36-9Relevant articles and documents
Mechanism of the polarographic reduction of 5-bromo-5-nitro-1,3-dioxane (Bronidox)
Rath,Hoffmann
, p. 443 - 448 (2007/10/03)
The electrochemical behavior at the dropping mercury electrode (DME) of 5-bromo-5-nitro-1,3-dioxane (BND), a preservative used in cosmetic preparations, was investigated. BND is reduced in 5 waves. The first wave (E(1/2)=+0.2 V) corresponds to the cleavage of bromide, giving 5-nitro-1,3- dioxane-anion (NDA). The second wave (E(1/2)= -0.2 V) is caused by adsorption. NDA is protonated, giving 5-nitro-1,3-dioxane (ND) which is reduced at E(1/2) = -0.6 V. In parallel to the electrochemical reduction ND is also formed by the chemical reaction of BND with metallic mercury. The reduction of the remaining adsorbed NDA at the DME is responsible for the fourth wave (E(1/2) = -1.1 V). Both ND and NDA are reduced to 1,3-dioxa-5- cyclohexylhydroxylamine (DCH). Finally DCH is reduced to 1,3-dioxa-5- cyclohexylamine (DCA). The reduction products were isolated, identified and a reduction mechanism is proposed.
Electrochemical behaviour of 5-nitro-1,3-dioxane
Rath,Hoffmann
, p. 842 - 846 (2007/10/03)
5-Nitro-1,3-dioxane (ND) is an intermediate in the polarographic reduction of 5-bromo-5-nitro-1,3-dioxane (Bronidox) which is used as a preservative in cosmetic preparations. The electrochemical behavior of ND was investigated by polarographic techniques, cyclic voltammetry and controlled-potential electrolysis. The reduction products were isolated, identified and a reduction mechanism at the DME is proposed. In dependence of the pH of the medium, equilibria between the nitro-form and the tautomeric aci-forms establish. Only the first one is polarographically active, the aci-forms do not undergo reduction at the DME. ND is reduced in two irreversible waves. The first wave is diffusion-controlled, 4 electrons per molecule ND are consumed and 1,3-dioxa-5-cyclohexyldroxylamine (DCH) is formed. In a second step DCH is reduced to 1,3-dioxa-5-cylohexylamine (DCA) with the uptake of 2 electrons. The limiting current is controlled by a catalytic reaction.