Low temperature hydrogenation of polycyclic aromatic hydrocarbons (PAH's) by tetralin in a molten salt catalyst
The reactions of phenanthrene, pyrene, anthracene, and naphthacene (tetracene) with tetralin at 80/sup 0/C in neat aprotic SbCl/sub 3/ were studied by in situ /sup 1/H NMR and by determining the reaction stoichiometry via product analysis following quench and separation procedures. Pyrene and phenanthrene did not react with tetralin in the neat SbCl/sub 3/, but anthracene and naphthacene reacted very rapidly and are slightly hydrogenated to 9,10-dihydroanthracene and 5,12 dihydronaphthacene. The product distribution and the reaction stoichiometry were found to depend on the amount of tetralin initially present. Knowledge of electron spin resonance studies indicating that phenanthrene and pyrene are not oxidized by SbCl/sub 3/ to radical cations but that the more easily oxidized polyaromatic hydrocarbons (PAH), anthracene and naphthacene do not form radical cations in SbCl/sub 3/ and the observation of redox driven reactions in SbCl/sub 3/ in which Sb/sup 3 +/ acts as an oxidant, combine to suggest that the unusual low temperature hydrogenation reactions reported herein proceed via reaction of the PAH radical cation with tetralin. (BLM)
- Research Organization:
- Oak Ridge National Lab., TN
- DOE Contract Number:
- W-7405-ENG-26
- OSTI ID:
- 6041031
- Report Number(s):
- CONF-810813-(Absts)
- Journal Information:
- Prepr. Pap. - Am. Chem. Soc., Div. Fuel Chem.; (United States), Journal Name: Prepr. Pap. - Am. Chem. Soc., Div. Fuel Chem.; (United States) Vol. 26:3; ISSN ACFPA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
010403* -- Coal & Coal Products-- Hydrogenation-- (-1987)
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301 -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ANTIMONY CHLORIDES
ANTIMONY COMPOUNDS
AROMATICS
CARBONACEOUS MATERIALS
CATALYSIS
CATALYTIC EFFECTS
CHEMICAL REACTIONS
CHLORIDES
CHLORINE COMPOUNDS
COAL
CONDENSED AROMATICS
ENERGY SOURCES
FOSSIL FUELS
FUELS
HALIDES
HALOGEN COMPOUNDS
HYDROCARBONS
HYDROGEN 1
HYDROGEN ISOTOPES
HYDROGENATION
ISOTOPES
LIGHT NUCLEI
MAGNETIC RESONANCE
MATERIALS
NUCLEAR MAGNETIC RESONANCE
NUCLEI
ODD-EVEN NUCLEI
ORGANIC COMPOUNDS
PHENANTHRENE
POLYCYCLIC AROMATIC HYDROCARBONS
PYRENE
RESONANCE
STABLE ISOTOPES
TETRACENE
TETRALIN