Oxidative Denitrogenation of Coal Liquids

The oxidative denitrogenation of quinoline (as a model compound representing the nitrogen containing structure of coal liquids) has been investigated in two steps: oxidation by perdecanoic acid at 50 °C to produce quinoline N-oxide in order to weaken the nitrogen-carbon bond; thermal decomposition of quinoline N-oxide to remove nitrogen as its respective oxides. Quinoline is successfully converted to quinoline N-oxide in the oxidation step. Thermal decomposition of quinoline N-oxide at 400 °C and 600 kPa of N2 produces 52-wt% quinoline, 22-wt% a condensed polymeric compound and 26-wt% gaseous mixture of CO2, CO and O2. Almost all the nitrogen content of quinoline N-oxide has remained in the residue of decomposition reaction. This confirms that thermal decomposition not only fails to remove nitrogen from structure of the oxidized molecule, but it also leads to production of a more complex aromatic structure with 10.4-wt% nitrogen content, compared to 10.6-wt% nitrogen content of quinoline.