Cyano-arenes produced by combustion of nitrogen-containing fuels

Abstract

Cyanonaphthalenes (both isomers) and cyanoacenaphthylenes (four isomers) were identified in the soot generated by the combustion of aromatic hydrocarbon fuels doped with 6-30% pyridine. These were by far the most abundant nitrogen-containing organic compounds in this combustion effluent; multiring, nitrogen heterocyclic compounds, such as those commonly observed in airborne particulate matter, were a minor component. These identifications were made by gas chromatographic mass spectrometry following a preliminary separation by alumina column chromatography. The environmental significance of these findings is discussed.Certain organic compounds in soot cause cancer in man (1).

Cyanoarenes in soot: synthesis and mutagenicity of cyanoacenaphthylenes

“…Dubay and Hites (4) have recently burned a model fuel containing 1-6% nitrogen and have identified the major azaarenes associated with this soot. The procedure involved Soxhlet extraction of the compounds from soot with CH2CI2, the separation of the azaarenes from the bulk of the PAH by column chromatography, and the separation and identification of the individual azaarenes using gas chromatography (GC) and gas chromatographic mass spectrometry (GC-MS).…”

Nitrated polycyclic aromatic hydrocarbons in urban air particles

“…Bjarseth and Eklund identified some PAH-carbonitriles in the working atmospheres of coke and aluminum plants (31). Several PAHcarbonitriles were identified by Dubay and Hites (32) by combustion of pyridine and xylene in a wick-fed alcohollamp burner. The finding of these compounds in the present sample indicates that PAH-carbonitriles may be ubiquitous in the environment as a result of combustion of nitrogen-containing organic material.…”

Characterization of microbial mutagens in complex samples—methodology and application

“…185 Carbonitrile derivatives of PAH (cyanoarenes) have also been found in soot generated by the combustion of nitrogencontaining aromatic fuels. 187 Fractionation of a sample from an aluminum smelting plant by the same HPLC procedure showed more of its mutagenic activity in the moderately polar fraction compared to the combustion samples mentioned above. 210 Since the aluminum smelting is a reductive process, it is conceivable that the polycyclic organic compounds formed should contain less oxygen and thereby be of less polar character than those formed during a combustion with excess air.…”