Nitrobenzene → Aniline

Participants

Reaction Conditions

Reaction Steps

12.3 g (0.100 mole nitrobenzene) in 75 ml of methanolic solution and 0.128 g Ru3 (CO)12 (600 microgram-atoms ruthenium) were placed in the reactor vessel. The gas volume in the vessel was replaced with carbon monoxide and then pressurized at ambient temperature with 920 psig carbon monoxide and 80 psig hydrogen (approximately 0.05 mole hydrogen). The reactor contents were then heated to 160° C. Initially, aniline was produced from nitrobenzene in 100 percent selectivity. After approximately 0.030 moles aniline had been produced, phenyl urethane production also began. After a total of 7.5 hours at 160° C., nitrobenzene conversion was complete and the solution contained 0.060 moles aniline and 0.034 moles phenyl urethane. This example demonstrates that the primary amine may be provided by reduction of the nitrogen-containing organic compound, e.g. nitrobenzene, in-situ. Note that, once the added hydrogen is utilized to reduce the nitrobenzene to aniline, the selectivity of the conversion of the remaining nitrobenzene to the urethane is greater than 50 percent.

Provenance & Evidence