Carbon monoxide-hydrogen-water: reduction of anthracene, dihydroanthracene, and quinoline
- Univ. of North Dakota, Grand Forks
Anthracene is reduced by CO-H/sub 2/O, CO-H/sub 2/O-H/sub 2/, or H/sub 2/ at 425/sup 0/C and an initial pressure of 1500 psi to dihydroanthracene, 1,2,3,4-tetrahydroanthracene, and methylbenzohydrindene. Hydrocracked products and dimers are formed to a minor extent. The hydrogen donor solvent, tetralin, promotes rearrangement and cracking. Tetralin also increases the formation of methylbenzohydrindene, but does not influence the overall conversion. Ferrous sulfide promotes rearrangement and cracking while lowering the overall conversion. Sodium carbonate retards the reaction. Dihydroanthracene disproportionates to anthracene and tetrahydroanthracene under the reaction conditions. The principal reduction product of quinoline under similar conditions is 1,2,3,4-tetrahydroquinoline. Fragmented aniline derivatives, dimeric quinoline species, and methylated compounds are also found in the reaction mixture. Hydrogen is most effective as a reducing gas, and carbon monoxide must have water present to accomplish the reduction. Iron sulfide and sodium carbonate promote the carbon monoxide reductions.
- OSTI ID:
- 6863602
- Journal Information:
- J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Journal Issue: 15 Vol. 43:15; ISSN JOCEA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ANTHRACENE
AROMATICS
AZINES
CARBON COMPOUNDS
CARBON MONOXIDE
CARBON OXIDES
CHALCOGENIDES
CHEMICAL REACTIONS
CONDENSED AROMATICS
CRYOGENIC FLUIDS
ELEMENTS
FLUIDS
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
HYDROGEN
HYDROGEN COMPOUNDS
NONMETALS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
OXIDES
OXYGEN COMPOUNDS
PYRIDINES
QUINOLINES
REDUCTION
WATER