Selective hydrogenation of polynuclear heteroatomic compounds. Final report
This research program focused on the utilization of polymer-supported (polystyrene-divinylbenzene, PS-DVB) transition-metal catalysts in the selective catalytic hydrogenation of polynuclear heteroaromatic compounds that are known to be present in coal and coal liquids. We found that the polymer-supported chlorotris(triphenyl-phosphine)rhodium(1) was the most efficient catalyst for the regiospecific reduction of the nitrogen-containing ring in model-coal compounds such as quinoline, 5,6- and 7,8-benzoquinoline and acridine, and in one case, a heteroaromatic sulfur compound, benzothiophene. Interestingly, the polymer-supported rhodium catalyst was more active than the corresponding homogeneous analogue by relative rate factors of 10 to 20 depending on the substrate studied in the reduction. More importantly, a model coal liquid was found to have a relative rate of reduction of quinoline to 1,2,3,4-tetrahydroquinoline (THQ) that was 2.2 times faster than a similar experiment without the coal liquid constituents consisting of pyrene, tetralin, methylnaphthalene, p-cresol, quinoline, and 2-methylpyridine. Further experimentation clearly showed that the model coal liquid constituent, p-cresol, was responsible for the relative rate enhancement in the highly regiospecific (no other model coal liquid constituent was hydrogenated) reduction of quinoline to THQ. We also found that 9,10-dihydrophenanthridine was an excellent catalytic transfer hydrogenation reagent in the presence of several homogeneous and polymer-supported transition-metal catalysts. A discussion demonstrates the potential usefulness of these catalysts in the hydroprocessing of coal liquids and other petroleum products.
- Research Organization:
- Lawrence Berkeley Lab., CA (USA)
- DOE Contract Number:
- AC03-76SF00098
- OSTI ID:
- 5289775
- Report Number(s):
- EPRI-AP-4227; ON: DE85017581
- Country of Publication:
- United States
- Language:
- English
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Regioselective hydrogenation of polynuclear heteroaromatic compounds catalyzed by polymer-supported transition metal complexes: initial rates, mechanism of reduction, model coal liquid experiment, role of p-cresol in rate enhancement of nitrogen ring reduction, catalytic transfer hydrogenation
Selective catalytic hydrogenation of polynuclear heteroaromatic nitrogen compounds with polymer-supported transition-metal compounds. [Quinoline, 5,6- and 7,8-benzoquinoline, acridine and phenanthridine]
Related Subjects
010405* -- Coal
Lignite
& Peat-- Hydrogenation & Liquefaction
ACRIDINES
AROMATICS
AZAARENES
AZINES
CARBONACEOUS MATERIALS
CATALYST SUPPORTS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL REACTIONS
COAL
COAL LIQUIDS
CONDENSED AROMATICS
CRESOLS
ELEMENTS
ENERGY SOURCES
FLUIDS
FOSSIL FUELS
FUELS
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
HYDROGEN TRANSFER
HYDROGENATION
HYDROXY COMPOUNDS
LIQUIDS
MAGNETIC RESONANCE
MATERIALS
METALS
NUCLEAR MAGNETIC RESONANCE
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
PHENOLS
PLATINUM METALS
POLYCYCLIC AROMATIC HYDROCARBONS
PROCESSING
PYRENE
PYRIDINES
QUINOLINES
REFINING
RESONANCE
RHODIUM
SPECIFICITY
STRUCTURAL MODELS
TETRALIN
THIONAPHTHENES
TRANSITION ELEMENTS