Detection of Benz[f]indene among the Pyrolysis Products of Coal and Anthracene

Abstract

Using high-pressure liquid chromatography with diode-array ultraviolet−visible detection, we have identified benz[f]indene (C13H10) among the pyrolysis products of coal and the model compound anthracene, a three-ring compound representative of the aromatic moieties in coal. The coal pyrolysis experiments are conducted at 700−1000 °C in a fluidized bed reactor; the anthracene experiments, at 900−1000 °C in a laminar flow reactor. This is the first time that benz[f]indene has been identified as a product of either fuel, coal or anthracene. Oxidative ring rupture is proposed as the mechanism responsible for the formation of benz[f]indene and other indene benzologues in these products.

Strong Acidity of Some Polycyclic Aromatic Compounds Annulated to a Cyclopentadiene Moiety and Their Cyano Derivatives – A Density Functional B3LYP Study

“…Their salts might thus provide new superconductive materials and/or other polymeric systems with novel properties. [66,67] It is important to mention that the parent hydrocarbons 1a, [35][36][37][38] 2a, [39,40] 3a [41] and 4a [42,43] have already been synthetized in laboratories.…”

“…It will turn out that the latter exerts a dramatic change in acidity leading to some extremal values in the gas phase and in DMSO. It is gratifying and very important to stress that the chemistry of the cyano group is well known, [32][33][34] and that the parent cyclopentadiene-annulated polycyclic aromatic hydrocarbons 1a, [35][36][37][38] 2a, [39,40] 3a [41] and 4a [42,43] have already been prepared and are known in the literature. Scheme 1.…”

Analysis of pyrolysis products from light hydrocarbons and kinetic modeling for growth of polycyclic aromatic hydrocarbons with detailed chemistry

“…The possible C 13 H 10 isomers are 1-methylbiphenylene, 2-methylbiphenylene, benz[-f]indene, benz[e]indene, and so on. Wornat et al first identified benz[f]indene among the pyrolysis products of anthracene using high-pressure liquid chromatography with diode-array ultraviolet-visible detection [24]. They also found benz[f]indene in the pyrolysis products of catechol [25].…”

“…They also found benz[f]indene in the pyrolysis products of catechol [25]. Although we are currently unable to identify these peaks because of commercial inavailability and lack of mass spectrum data of this compound, it is not daring to assign benz[f]indene to one of these undefined peaks and to assert its presence in the products of the light hydrocarbon pyrolysis based on the evidences that the precursor ion mass number is 166 m/z and the findings of Wornat et al [24,25].…”

How to add a five-membered ring to polycyclic aromatic hydrocarbons (PAHs) – molecular mass growth of the 2-naphthyl radical (C10H7) to benzindenes (C13H10) as a case study

“…Wornat et al stated that benz[f]indene could be formed via molecular oxygen addition to the 1-or 2-anthryl radical, followed by carbon monoxide elimination and hydrogen loss (Scheme 6). 82 This oxy radical pathway could dominate above 900 K as analogous to the reaction of phenyl plus molecular oxygen. 83,84 Similarly, phenanthrenyl radicals can also lead to C13H10 isomers (Scheme 7).…”