The Oxynitration of Benzene. I. Studies Relating to the Reaction Mechanisms¹

THE OXYNITRATION OF BENZENE TO 2,4-DINITROPHENOL1

“…The effect on the yield was determined by a batch procedure while the effect on the rate of the reaction was studied more conveniently by a continuous process. 3 A temperature of 50°was found to be the optimum temperature for preparing 2,4-dinitrophenol by the oxynitration reaction by our procedure. At higher temperatures more of the 2,4-dinitrophenol was nitrated to picric acid with consequent lowering in yield, and more nitrobenzene was produced; thus, at 70°t he combined yield of 2,4-dinitrophenol (16.9%) and picric acid (37.7%) was only 54.6% and the yield of nitrobenzene was 17-19%.…”

“…In this process, discovered by Wolff enstein and Boeters (1), benzene is converted into picric acid by the action of a hot solution of mercuric nitrate in nitric acid. The history and mechanism of the oxynitration reaction have been discussed in recent papers (2,3).…”