The mechanism of nitration of diphenylamine in the nitric acid - acetic anhydride system
Degree GrantorUniversity of Canterbury
Degree NameMaster of Science
Acetic anhydride is widely used as a solvent for the nitration of compounds susceptible to oxidation or hydrolytic attack by aqueous mixed acid. While the mechanism for nitration in aqueous mixed acid and for nitric acid solutions in a number of inert solvents is well established, until recently little was known of the mechanism of nitration in acetic anhydride. In the work described in this thesis, the kinetics of the nitration have been studied. Reactions were followed by spectrophotometric absorption measurements. The effects that addition of acetic acid, tetradeutero acetic acid, sulphuric acid and lithium nitrate have on the reaction rates were investigated. From the results obtained a reaction path is suggested and the mechanism of nitration of o-xylene and diphenylamine are discussed.