Aromatic hydrocarbon growth from indene |
| |
Authors: | Lu M Mulholland J A |
| |
Institution: | Environmental Engineering, Georgia Institute of Technology, Atlanta 30332-0512, USA. |
| |
Abstract: | Aromatic hydrocarbon growth from indene (C9H8), which contains the five-membered ring cyclopentadienyl moiety, was investigated experimentally in a 4 s flow reactor over a temperature range 650-850 degrees C. Major products observed were three C18H12 isomers (chrysene, benza]anthracene and benzoc]phenanthrene), two C17H12 isomers (benzoa]fluorene and benzob]fluorene), and two C10H8 isomers (naphthalene and benzofulvene). Reaction pathways to these products are proposed. Indenyl radical addition to indene produces a resonance-stabilized radical intermediate which further reacts by one of two routes. Rearrangement by intramolecular addition produces a bridged structure that leads to the formation of C17H12 and C10H8 products. Alternatively, beta scission produces biindenyl, which leads to the formation of C18H12 products by a ring condensation mechanism analogous to that proposed for cyclopentadiene-to-naphthalene conversion. Temperature dependencies of both the partitioning between these two routes and the product isomer distributions are consistent with thermochemical modeling using semi-empirical molecular orbital methods. The results further illustrate the role of resonance-stabilized radical rearrangement in aromatic growth and condensation of systems with cyclopentadienyl moieties. |
| |
Keywords: | |
本文献已被 ScienceDirect PubMed 等数据库收录! |
|