Study of the aromatic by-products formed from ozonation of anilines in aqueous solution
Judith Sarasa1, Susana Cortés, Peñia Ormad
1Department of Chemical Engineering and Environmental Technology, University of Zaragoza, Spain. jsarasa@posta.unizar.es
Abstract:
Aqueous solutions of aniline and p-chloroaniline were treated with ozone in order to study the reaction and oxidation by-products. Aniline solutions were ozonated at low and high pH, so as to compare both molecular and hydroxyl free radical mechanisms, respectively. The main identified aromatic by-products were nitrobenzene and azobenzene when the experiment was carried out at acid pH. Formation of nitrobenzene, azobenzene, azoxybenzene and 2-pyridine-carboxylic was observed when the ozonation was carried out at basic pH. p-Chloroaniline was treated with ozone only at high pH and the identified by-products were in accordance with those obtained in the ozonation of aniline: p-chloronitrobenzene, 4,4'-dichloroazobenzene and 4-chloro-2-pyridine-carboxylic acid. All the aromatic by-products found were less toxic than the raw materials. The pseudo-first-order constants in aniline concentration were calculated, whilst kinetic in p-chloroaniline concentration could not be adjusted to a first-order reaction.
More Related Videos
Related Concept Videos
Oxidative Cleavage of Alkenes: Ozonolysis
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Basicity of Aromatic Amines
Preparation of Amines: Reduction of Oximes and Nitro Compounds
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...


