Hydrodenitrogenation of quinoline and acridine
The hydrodenitrogenation of quinoline and of acridine was studied in a batch autoclave reactor between 342 and 353/sup 0/C and between 500 and 2000 psig. The several commercial hydrotreating catalysts examined decreased in activity in the following order for quinoline hydrodenitrogenation: Ni--Mo/Al/sub 2/O/sub 3/, Ni--W/Al/sub 2/O/sub 3/, Ni--W/SiO/sub 2/--Al/sub 2/O/sub 3/, and Co--Mo/Al/sub 2/O/sub 3/. The total nitrogen removal rate for quinoline was slightly greater than that for acridine and both followed pseudo first-order kinetics over a conversion range of 0 to 50%. Hydrogenation and cracking steps were both kinetically limiting. Nitrogen-containing reaction products for quinoline hydrodenitrogenation were 1,2,3,4-tetrahydroquinoline, 5,6,7,8-tetrahydroquinoline, decahydroquinoline and o-propylaniline. At 342/sup 0/C and 500 psig quinoline and 1,2,3,4-tetrahydroquinoline were in thermodynamic equilibrium, and the disappearance of the lumped group of quinoline plus 1,2,3,4-tetrahydroquinoline followed pseudo first-order kinetics. Sixteen nitrogen-containing reaction products were found for acridine hydrodenitrogenation, including 1,2,3,4-tetrahydroacridine, 1,2,3,4,9,10,13,14-octahydroacridine, sym-octahydroacridine, perhydroacridine, and o-(methylenecyclohexane)aniline. The hydrogenolysis step for both quinoline and acridine appears to be through hydrogenated forms of these compounds. This is supported by bond strength arguments.
- Research Organization:
- Delaware Univ., Newark (USA). Coll. of Engineering
- Sponsoring Organization:
- US Energy Research and Development Administration (ERDA)
- DOE Contract Number:
- EX-76-C-01-2028
- OSTI ID:
- 6577411
- Report Number(s):
- FE-2028-14
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ACRIDINES
ALUMINIUM COMPOUNDS
ALUMINIUM OXIDES
AZINES
CATALYSTS
CATALYTIC EFFECTS
CHALCOGENIDES
CHEMICAL REACTIONS
COBALT COMPOUNDS
CRYOGENIC FLUIDS
DENITRIFICATION
ELEMENTS
FLUIDS
HETEROCYCLIC COMPOUNDS
HIGH TEMPERATURE
HYDROGENATION
MEDIUM PRESSURE
MOLYBDENUM COMPOUNDS
NICKEL COMPOUNDS
NITROGEN
NONMETALS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
OXIDES
OXYGEN COMPOUNDS
PYRIDINES
QUINOLINES
SILICON COMPOUNDS
SILICON OXIDES
TRANSITION ELEMENT COMPOUNDS
TUNGSTEN COMPOUNDS