Decomposition and oligomerization of 2,3-naphthyridine under high-pressure and high-temperature conditions

The chemical reaction of 2,3-naphthyridine, a nitrogen-containing aromatic compound, was investigated at pressures ranging from 0.5 to 1.5 GPa and temperatures from 473 to 573 K. A distinct decrease in the amount of residual 2,3-naphthyridine was observed in the samples recovered after reaction at ˃523 K at 0.5 and 1.0 GPa, and ˃548 K at 1.5 GPa. The formation of o-xylene and o-tolunitrile accompanied a decreasing N/C ratio of the reaction products, indicating decomposition of the aromatic ring and release of nitrogen. Precise analysis of the reaction products indicated the oligomerization of decomposed products with the residual 2,3-naphthyridine to form larger molecules up to 7mers. Nitrogen in the aromatic ring accelerated reactions to decompose the molecule and to oligomerize at lower temperatures than those typically reported for aromatic hydrocarbon oligomerization. The major reaction mechanism was similar between 0.5 and 1.5 GPa, although larger products preferentially formed in the samples at higher pressure.