Hydrogenation, cracking and hydrogenolysis of bibenzyl in a high-pressure stirred autoclave
The extent to which coal liquefaction catalysts promote the cleavage of aliphatic bridges was investigated. Bibenzyl was chosen as a model to represent an ethyl bridge between two aromatic centers. An initial screening of catalysts showed that Co molybdate on SiO/sub 2/-promoted Al/sub 2/O/sub 3/, WS/sub 2/, LiCl-SnCl/sub 2/, SnCl/sub 2/ promoted with NH/sub 4/Cl, ZnCl/sub 2/, and SbCl/sub 3/ were all inactive as catalysts. FeCl/sub 3/ caused the bibenzyl to undergo a disproportionation reaction yielding benzene plus a tarry substance. AlCl/sub 3/ brought about a complete conversion of bibenzyl to benzene, toluene, and ethylbenzene as the primary products and lesser amounts of cyclohexane- and diphenyl-type derivatives, as well as a tarry substance. p-Toluenesulfonic acid was found to decompose but did not cause the formation of products from bibenzyl. More extensive experiments were then performed with AlCl/sub 3/. Product yields and distributions as a function of temperature, H/sub 2/ pressure, and catalyst concentration were determined. Participation of benzene, the solvent, in these reactions was also investigated. Bibenzyl conversion and the yields of toluene and ethylbenzene were a strong function of temperature and catalyst concentration but not of H/sub 2/ pressure. The yield of cyclohexane derivatives increased with pressure. This suggested that the H/sub 2/ needed to form toluene and ethylbenzene is derived from the reactant or solvent but not from dissolved H/sub 2/. Conversely, the formation of cyclohexane derivatives does involve the consumption of dissolved H/sub 2/. Plausible mechanisms are discussed.
- Research Organization:
- California Univ., Berkeley (USA). Lawrence Berkeley Lab.
- DOE Contract Number:
- W-7405-ENG-48
- OSTI ID:
- 7356423
- Report Number(s):
- LBL-4440
- Country of Publication:
- United States
- Language:
- English
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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301 -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ALKALI METAL COMPOUNDS
ALKANES
ALUMINIUM CHLORIDES
ALUMINIUM COMPOUNDS
ALUMINIUM OXIDES
AMMONIUM COMPOUNDS
ANTIMONY CHLORIDES
ANTIMONY COMPOUNDS
AROMATICS
AUTOCLAVES
BENZENE
BIBENZYL
CARBONACEOUS MATERIALS
CATALYSTS
CHALCOGENIDES
CHEMICAL COMPOSITION
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
CHLORIDES
CHLORINE COMPOUNDS
COAL
COAL LIQUEFACTION
COBALT COMPOUNDS
CRACKING
CRYOGENIC FLUIDS
CYCLOALKANES
CYCLOHEXANE
DECOMPOSITION
ELEMENTS
ENERGY SOURCES
FLUIDS
FOSSIL FUELS
FUELS
HALIDES
HALOGEN COMPOUNDS
HIGH PRESSURE
HIGH TEMPERATURE
HYDROCARBONS
HYDROGEN
HYDROGENATION
IRON CHLORIDES
IRON COMPOUNDS
KINETICS
LIQUEFACTION
LITHIUM CHLORIDES
LITHIUM COMPOUNDS
LITHIUM HALIDES
MINERALS
MOLECULAR STRUCTURE
MOLYBDATES
MOLYBDENUM COMPOUNDS
NONMETALS
ORGANIC COMPOUNDS
ORGANIC SOLVENTS
OXIDATION
OXIDES
OXYGEN COMPOUNDS
PRESSURE DEPENDENCE
PYROLYSIS
REACTION KINETICS
REDUCTION
SILICA
SILICON COMPOUNDS
SILICON OXIDES
SOLVENTS
SULFIDES
SULFUR COMPOUNDS
TIN CHLORIDES
TIN COMPOUNDS
TIN HALIDES
TOLUENE
TRANSITION ELEMENT COMPOUNDS
TUNGSTEN COMPOUNDS
TUNGSTEN SULFIDES
ZINC CHLORIDES
ZINC COMPOUNDS
ZINC HALIDES