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http://dx.doi.org/10.4491/eer.2007.12.5.211

Thermal Formation of Polycyclic Aromatic Hydrocarbons from Cyclopentadiene (CPD)  

Kim, Do-Hyong (Department of Civil and Environmental Engineering, Georgia Institute of Technology)
Kim, Jeong-Kwon (Department of Environmental Engineering, Dong-Eui University)
Jang, Seong-Ho (Department of Regional Environmental System Engineering, Pusan National University)
Mulholland, James A. (Department of Civil and Environmental Engineering, Georgia Institute of Technology)
Ryu, Jae-Yong (R&D Planning & Management Office, Korea Institute of Environmental Science and Technology (KIEST))
Publication Information
Environmental Engineering Research / v.12, no.5, 2007 , pp. 211-217 More about this Journal
Abstract
Polycyclic aromatic hydrocarbon growth from cyclopentadiene (CPD) pyrolysis was investigated using a laminar flow reactor operating in a temperature range of 600 to $950^{\circ}c$. Major products from CPD pyrolysis are benzene, indene and naphthalene. Formation of observed products from CPD is explained as follows. Addition of the cyclopentadienyl radical to a CPD $\pi$-bond produces a resonance-stabilized radical, which further reacts by one of three unimolecular channels: intramolecular addition, C-H bond $\beta$-scission, or C-C bond $\beta$-scission. The intramolecular addition pathway produces a 7-norbornenyl radical, which then decomposes to indene. Decomposition by C-H bond $\beta$-scission produces a biaryl intermediate, which then undergoes a ring fusion sequence that has been proposed for dihydrofulvalene-to-naphthalene conversion. In this study, we propose C-C bond $\beta$-scission pathway as an alternative reaction channel to naphthalene from CPD. As preliminary computational analysis, Parametric Method 3 (PM3) molecular calculation suggests that intramolecular addition to form indene is favored at low temperatures and C-C bond $\beta$-scission leading to naphthalene is predominant at high temperatures.
Keywords
PAH (Polycyclic aromatic hydrocarbon); CPD (Cyclopentadiene); Thermal formation;
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