Thermolysis of bibenzyl: roles of sulfur and hydrogen sulfide
The presence of sulfur in the thermolysis of bibenzyl considerably reduces the severity of the conditions required to cleave the aliphatic carbon-carbon bond. Bibenzyl rapidly reacts with sulfur at 425/sup 0/C to give nine fully characterized products: benzene, toluene, ethylbenzene, diphenylmethane, 1,1-diphenylethane, trans-stilbene, phenanthrene, 2-phenylbenzothiophene, and 2,3,4,5-tetraphenylthiophene. Toluene is the principal product, and its yields are dependent on reaction time, temperature, and sulfur loading. With the addition of H/sub 2/S to the sulfur-bibenzyl reaction mixture, the required elemental sulfur loading for maximum toluene yields is greatly decreased, and the mass recovery decreases with amounts of sulfur loaded. The two minor products, 2-phenylbenzothiophene and 2,3,4,5-tetraphenylthiophene, give evidence of sulfur incorporation under these sulfur concentration conditions. The addition of hydrogen to the reaction mixtures improves mass recovery and decreases conversion. 27 references, 4 figures, 4 tables.
- Research Organization:
- Univ. of North Dakota, Grand Forks
- OSTI ID:
- 5262837
- Journal Information:
- J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 50:11; ISSN JOCEA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ALKYLATED AROMATICS
AROMATICS
BENZENE
BIBENZYL
BINDING ENERGY
CHALCOGENIDES
CONDENSED AROMATICS
DATA
DISSOCIATION
ELEMENTS
ENERGY
EXPERIMENTAL DATA
HEATING
HIGH TEMPERATURE
HYDROCARBONS
HYDROGEN
HYDROGEN COMPOUNDS
HYDROGEN SULFIDES
INFORMATION
NONMETALS
NUMERICAL DATA
ORGANIC COMPOUNDS
PHENANTHRENE
SULFIDES
SULFUR
SULFUR COMPOUNDS
TIME DEPENDENCE
TOLUENE