Coronene (hexabenzobenzene)

Technical Report ·

OSTI ID:7220533

Boente, L

Coronene (C/sub 24/H/sub 12/) is a relatively stable multi-ringed hydrocarbon consisting of six benzene rings symmetrically arranged about another central benzene ring. It melts at 432/sup 0/C and boils at 525/sup 0/C. It was first synthesized in 1932 in a long process by Scholl and Meyer, but was first produced in larger quantities in a hydrogenation process at I.G. Farbenindustrie, Ludwigshafen/Oppau. Reactions of coronene are discussed. Sulfur, halogen, and quinone-type derivatives are described, but mostly the hydrogenated forms of coronene are discussed. Coronene showed a great amount of resonance stabilization, so in attempts at hydrogenating it, it was found that hydrogen added at many points, essentially at once, so the only hydrogen derivatives which could be isolated were two isomeric perhydrocoronenes (C/sub 24/H/sub 36/; one melting at 370/sup 0/C, the other at 203/sup 0/C), obtained at 270/sup 0/C and 300 to 600 atm hydrogen pressure, and a relatively unstable dodecahydrocoronene (C/sub 24/H/sub 24/; melting at 353/sup 0/C). Coronene could be recovered from the hydrogenated forms by heating them with selenium at 360/sup 0/C. The dodecahydrocoronene crystallized in yellow rectangular platelets, but coronene (yellow) and the perhydrocoronenes (white) crystallized in long needles. Coronene was not very soluble, even in boiling mixtures, but sublimed very easily, so it sometimes caused stoppages of tubes by condensing out of hot gas. The fluorescence properties of these compounds, and the phosphorescence in different colors at different temperatures of a 98 percent perhydrocoronene; 2 percent coronene mixture are also discussed.

• Research Organization: I.G. Farbenindustrie, A.G., Ludwigshafen (Germany)
• OSTI ID: 7220533
• Report Number(s): TOM-1-6-17
• Country of Publication: United States
• Language: German

Related Subjects

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AROMATICS
CARBONACEOUS MATERIALS
CHEMICAL REACTIONS
COAL
COAL LIQUEFACTION
CONDENSED AROMATICS
CRYSTAL STRUCTURE
ELEMENTS
ENERGY SOURCES
FLUORESCENCE
FOSSIL FUELS
FUELS
HIGH PRESSURE
HIGH TEMPERATURE
HYDROGENATION
LIQUEFACTION
LUMINESCENCE
ORGANIC COMPOUNDS
PHOSPHORESCENCE
PHYSICAL PROPERTIES
PRODUCTION
SELENIUM
SEMIMETALS
THERMOCHEMICAL PROCESSES