Gas-phase hydrodenitrogenation reactions of polynuclear heteroaromatic nitrogen compounds and selected intermediates with a 50% nickel oxide/aluminate supported on silica-alumina catalyst

Journal Article · Tue May 01 00:00:00 EDT 1990 · Journal of Catalysis; (USA)

DOI:https://doi.org/10.1016/0021-9517(90)90158-G· OSTI ID:6469277

Fish, R H; Heinemann, H ^[1]; Michaels, J N; Moore, R S ^[2]

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1. Lawrence Berkeley Lab., CA (USA)
2. Univ. of California, Berkeley (USA)

The gas-phase hydrodenitrogenation (HDN) of quinoline, 1,2,3,4-tetrahydroquinoline, 2-propylaniline, and propylbenzene with a 50% nickel oxide/aluminate on SiO{sub 2}-Al{sub 2}O{sub 3} catalyst has been studied at 250{degree}C under 1 atm of hydrogen gas. Under these mild conditions, alkylaromatics are the predominant HDN products. In the reaction network of this catalytic process, quinoline is hydrogenated to 1,2,3,4-tetrahydroquinoline, which subsequently undergoes C-N bond hydrogenolysis to form 2-propylaniline and then propylbenzene. Significant alkyl side-chain hydrogenolysis occurs in parallel to these reactions, producing a mixture of alkylanilines and alkylbenzenes. Small amounts of alkylcyclohexanes are produced by hydrogenation of the alkylbenzenes. This network differs significantly from that of commercial HDN processes in which quinoline is hydrogenated fully to decahydroquinoline prior to C-H bond cleavage. Pseudo-first-order rate constants have been estimated for quinoline hydrogenation, alkylaniline formation, alkylaniline HDN, and alkylbenzene hydrogenation and compared to analogous data for commercial HDN. This comparison indicates that the activity of the nickel oxide/aluminate on SiO{sub 2}-Al{sub 2}O{sub 3} catalyst is within an order of magnitude of the activity of commercial HDN catalysts. The nickel oxide catalyst is irreversibly poisoned by sulfur and slowly deactivates during HDN due to coke formation; the coked catalyst can be regenerated by oxidation in air and subsequent reduction in hydrogen.

• DOE Contract Number: AC03-76SF00098
• OSTI ID: 6469277
• Journal Information: Journal of Catalysis; (USA), Journal Name: Journal of Catalysis; (USA) Vol. 123:1; ISSN 0021-9517; ISSN JCTLA
• Country of Publication: United States
• Language: English

Related Subjects

01 COAL, LIGNITE, AND PEAT
010402 -- Coal
Lignite
& Peat-- Purification & Upgrading
02 PETROLEUM
020400* -- Petroleum-- Processing
AIR
ALUMINATES
ALUMINIUM COMPOUNDS
ALUMINIUM OXIDES
AMINES
ANILINE
AROMATICS
ATMOSPHERIC PRESSURE
AZAARENES
AZINES
CATALYST SUPPORTS
CATALYTIC EFFECTS
CHALCOGENIDES
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
COKE
DEACTIVATION
DEHYDROGENATION
DENITRIFICATION
ELEMENTS
FLUIDS
GASES
HETEROCYCLIC COMPOUNDS
HIGH TEMPERATURE
HYDROGEN
HYDROGENATION
KINETICS
NICKEL COMPOUNDS
NICKEL OXIDES
NONMETALS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
OXIDATION
OXIDES
OXYGEN COMPOUNDS
POISONING
PYRIDINES
QUINOLINES
REACTION KINETICS
REDUCTION
REGENERATION
SILICON COMPOUNDS
SILICON OXIDES
SULFUR
SYNTHESIS
TRANSITION ELEMENT COMPOUNDS