The Hydrodenitrogenation of Quinoline Reaction Network

Abstract

Hydrodenitrogenation of quinoline catalyzed by a sulfided Ni-Mo/Al₂O₃ catalyst was investigated under hydrogen pressure of 12 MPa (cold charge) in the temperature range of 300 to 375°C. Reaction products were classified into five groups; (i) tetrahydroquinolines, decahydroquinolines and their isomers, (ii)nitrogen-containing ring-opening products (propylanilines, aminopropylcyclohexanes and their isomers), (iii)denitrogenated products (propylcyclohexane, propylcyclohexene, propylbenzene and their isomers), (iv)addition products (hydrocarbons of MW = 244, 250 and others and nitrogen-containing compounds of MW = 253, 257, 263 and others) and (v) cracked products (cyclohexane, methylcyclohexane and ethylcyclohexane).
The nitrogen-containing addi tion compounds are considered to be formed by addition of denitrogenated intermediate to carbon atom of nitrogen-containing species and to produce addition compounds without nitrogen atom by hydrodenitrogenation. The reaction network is proposed.