17219-94-2

Upstream product

• 85-01-8 phenanthrene 
• 201156-39-0 2,2'-Bis-(1-chloro-vinyl)-biphenyl 

Downstream Products

• 190-23-8 hexabenzotriphenylene 
• 84-11-7 9,10-phenanthrenequinone 

Relevant academic research and scientific papers

Behavior and prediction of photochemical degradation of chlorinated polycyclic aromatic hydrocarbons in cyclohexane

The photochemical degradation of 11 chlorinated polycyclic aromatic hydrocarbons (ClPAHs) and the corresponding 5 parent PAHs was examined to simulate the compound's fate on aerosol surfaces. All the ClPAHs and PAHs decayed according to the first-order reaction rate kinetics. The photolysis rates of ClPAHs varied greatly according to the skeleton of PAHs; the rates of chlorophenanthrenes (ClPhes) and 1-chloropyrene were higher than those of corresponding parent PAHs, whereas chlorofluoranthenes, 7-chlorobenz[a]anthracene and 6-chlorobenzo[a]pyrene were more stable under irradiation compared to respective parent PAH. Considering the photoproducts of ClPhes detected, the oxidation could occur immediately at positions of the highest frontier electron density. Finally, the quantitative structure-property relationship models were developed for direct photolysis half-lives and average quantum yields of the ClPAHs and parent PAHs, in which the significant factors affecting photolysis were ELUMO+1, total energy and surface area, and ELUMO, ELUMO - EHOMO and total energy, respectively.

Unexpected high temperature behaviour of 2,2′-diethynylbiphenyl in the gas phase - A precursor for acephenanthrylene instead of pyrene

Flash Vacuum Thermolysis (FVT) of 2,2′-diethynylbiphenyl (6) gave, instead of pyrene (5), acephenanthrylene (10) and fluoranthene (11) as major products. The unequivocal identification of 9-ethynylphenanthrene (12) at T ≤ 800°C suggests that 12 is the initial stable product derived from 6. It is documented that under high-temperature conditions in the gas phase compound 12 is efficiently converted into 10, which subsequently rearranges to 11. The formation of 12 from 6 is rationalized by invoking the transient formation of cyclobuta[l]phenanthrene (13) by intramolecular cyclization of the ethynyl moieties of 6 followed by a reiro-carbene C-H insertion and a 1,2-H shift. This interpretation is supported by the results of independent FVT of 2,2′-bis(1-chloroethenyl)biphenyl (15). Wiley-VCH Verlag GmbH, 1997.