Regioselective C-N bond cleavage in an {eta}{sup 2}(N,C)-coordinated pyridine and an {eta}{sup 1}(N) {r_arrow} {eta}{sup 2}(N,C) bonding rearrangement in coordinated quinoline: Models for hydrodenitrogenation catalysis
- Univ. of Arizona, Tucson, AZ (United States)
The catalytic removal of sulfur and nitrogen from petroleum feedstocks and coal-derived liquids is essential to preclude the poisoning of hydrocracking and reforming catalysts and to reduce emissions of their oxides. Industrial hydrodenitrogenation (HDN) is typically effected over sulfided CoMo/Al{sub 2}O{sub 3} or NiMo/Al{sub 2}O{sub 3} under conditions which remove nitrogen as NH{sub 3}. The nitrogen-containing compounds which are most difficult to process are the aromatic heterocycles such as pyridine, quinoline, and indole derivatives. One central question in HDN catalysis which remains unresolved concerns how the strong C-N bonds in these heterocycles are cleaved. Herein the authors provide evidence for an {eta}{sup 1}(N){r_arrow}{eta}{sup 2}(N,C) bonding rearrangement in model HDN substrates and demonstrate that nucleophilic attack of an {eta}{sup 2}(N,C)-pyridine results in facile, regioselective C-N bond cleavage. 17 refs., 3 figs.
- Sponsoring Organization:
- USDOE
- OSTI ID:
- 285001
- Journal Information:
- Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 13 Vol. 114; ISSN JACSAT; ISSN 0002-7863
- Country of Publication:
- United States
- Language:
- English
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