O-Xylene → 4-Nitrodiphenylamine

Participants

Reaction Conditions

Reaction Steps

Into the reactor previously described are charged 49.7 grams (0.315 moles) of p-nitrochlorobenzene together with 98.7 grams of a 66.4% solution of formanilide recovered from a previous run (0.54 molecular proportions). The solution also contained 0.07 moles of p-nitrochlorobenzene, bringing the total to 0.385 mole. About 50 milliliters of xylene are added, and the mixture heated to refluxing temperature which is about 195°-198° C. To the hot mixture is added at the rate of about 0.4 ml. per minute 82.5 grams (0.55 mole) of cesium hydroxide as a 50% solution in water (165 grams) during which addition the water is continuously removed. The heating is continued for a total time of about five hours, then 250 ml. of xylene is added and the xylene solution washed twice with 200 ml. portions of 90° C. water. The xylene solution is cooled to 5° C., filtered and the cake washed with 60 ml. of 5° C. xylene. There is obtained 40.7 grams of 4-nitrodiphenylamine. The total yield determined as described in Example 1 is 72%. The conversion of p-nitrodiphenylamine is 99.1%.

Provenance & Evidence