Nitration of particle-associated PAHs and their derivatives (nitro-, oxy-, and hydroxy-PAHs) with NO₃ radicals

The heterogeneous reactions of typical polycyclic aromatic hydrocarbons (PAHs) and their derivatives (nitro-, oxy-, and hydroxy-PAHs) adsorbed on azelaic acid particles with NO₃ radicals are investigated using a flow-tube reactor coupled to a vacuum ultraviolet photoionization aerosol time-of-flight...

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Published in	Atmospheric environment (1994) Vol. 45; no. 15; pp. 2515 - 2521
Main Authors	Zhang, Yang, Yang, Bo, Gan, Jie, Liu, Changgeng, Shu, Xi, Shu, Jinian
Format	Journal Article
Language	English
Published	Kidlington Elsevier Ltd 01.05.2011 Elsevier
Subjects	Aerosols anthracenes anthraquinones Applied sciences atmospheric chemistry Atmospheric pollution containers Derivatives Exact sciences and technology free radicals gas chromatography mass spectrometry Nitration Oxygenated Pollution Polyallylamine hydrochloride Pyrenes Radicals Reaction products NO Anthracene Hydrocarbon radicals Reaction product Nitrogen compounds Nitrates Organic anhydride Polycyclic aromatic compound Mutagen Ketone Real time system Persistent organic pollutant Carcinogen Pyrene Aerosols Air pollution PAHs Aerosol mass spectrometry Reactor Mass spectrometry Organic compounds Heterogeneous reaction Successive reaction
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Abstract	The heterogeneous reactions of typical polycyclic aromatic hydrocarbons (PAHs) and their derivatives (nitro-, oxy-, and hydroxy-PAHs) adsorbed on azelaic acid particles with NO₃ radicals are investigated using a flow-tube reactor coupled to a vacuum ultraviolet photoionization aerosol time-of-flight mass spectrometer (VUV-ATOFMS). The mono-nitro-, di-nitro-, and poly-nitro-products from successive nitro-substitution reactions of PAHs and their derivatives are observed in real time with VUV-ATOFMS. 9-Nitroanthracene, anthraquinone, anthrone, 9,10-dinitroanthracene, 2-, 4-, and 9-nitrophenanthrene, 1-nitropyrene, 1,3-, 1,6-, and 1,8-dinitropyrene, 7-nitrobenzo[a]anthracene, and benzo[a]anthracene-7,12-dione are identified by GC/MS analysis of the reaction products of PAHs and their derivatives coated on the inner bottom surface of the conical flasks with NO₃ radicals. Other oxygenated products are tentatively assigned. 1-Nitropyrene is the only mono-nitrated product detected in the reaction of surface-bound pyrene with gas-phase NO₃ radicals. This phenomenon is different from what has been observed in previous studies of the gas-phase pyrene nitration, showing that 2-nitropyrene is the sole nitration product. The experimental results may reveal the discrepancies between the heterogeneous and homogeneous nitrations of pyrene.
AbstractList	The heterogeneous reactions of typical polycyclic aromatic hydrocarbons (PAHs) and their derivatives (nitro-, oxy-, and hydroxy-PAHs) adsorbed on azelaic acid particles with NO3 radicals are investigated using a flow-tube reactor coupled to a vacuum ultraviolet photoionization aerosol time-of-flight mass spectrometer (VUV-ATOFMS). The mono-nitro-, di-nitro-, and poly-nitro-products from successive nitro-substitution reactions of PAHs and their derivatives are observed in real time with VUV-ATOFMS. 9-Nitroanthracene, anthraquinone, anthrone, 9,10-dinitroanthracene, 2-, 4-, and 9-nitrophenanthrene, 1-nitropyrene, 1,3-, 1,6-, and 1,8-dinitropyrene, 7-nitrobenzo[a]anthracene, and benzo[a]anthracene-7,12-dione are identified by GC/MS analysis of the reaction products of PAHs and their derivatives coated on the inner bottom surface of the conical flasks with NO3 radicals. Other oxygenated products are tentatively assigned. 1-Nitropyrene is the only mono-nitrated product detected in the reaction of surface-bound pyrene with gas-phase NO3 radicals. This phenomenon is different from what has been observed in previous studies of the gas-phase pyrene nitration, showing that 2-nitropyrene is the sole nitration product. The experimental results may reveal the discrepancies between the heterogeneous and homogeneous nitrations of pyrene. Highlightsao The reactions of aerosol-associated PAHs and their derivatives with NO3 radicals are carried out. ao The particle-phase reactants and their reaction products are analyzed in real time. ao Nitrated and oxygenated products are observed. ao The identification of the products by GC/MS is performed. The heterogeneous reactions of typical polycyclic aromatic hydrocarbons (PAHs) and their derivatives (nitro-, oxy-, and hydroxy-PAHs) adsorbed on azelaic acid particles with NO₃ radicals are investigated using a flow-tube reactor coupled to a vacuum ultraviolet photoionization aerosol time-of-flight mass spectrometer (VUV-ATOFMS). The mono-nitro-, di-nitro-, and poly-nitro-products from successive nitro-substitution reactions of PAHs and their derivatives are observed in real time with VUV-ATOFMS. 9-Nitroanthracene, anthraquinone, anthrone, 9,10-dinitroanthracene, 2-, 4-, and 9-nitrophenanthrene, 1-nitropyrene, 1,3-, 1,6-, and 1,8-dinitropyrene, 7-nitrobenzo[a]anthracene, and benzo[a]anthracene-7,12-dione are identified by GC/MS analysis of the reaction products of PAHs and their derivatives coated on the inner bottom surface of the conical flasks with NO₃ radicals. Other oxygenated products are tentatively assigned. 1-Nitropyrene is the only mono-nitrated product detected in the reaction of surface-bound pyrene with gas-phase NO₃ radicals. This phenomenon is different from what has been observed in previous studies of the gas-phase pyrene nitration, showing that 2-nitropyrene is the sole nitration product. The experimental results may reveal the discrepancies between the heterogeneous and homogeneous nitrations of pyrene.
Author	Yang, Bo Zhang, Yang Liu, Changgeng Shu, Jinian Gan, Jie Shu, Xi
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Keywords	NO Anthracene Hydrocarbon radicals Reaction product Nitrogen compounds Nitrates Organic anhydride Polycyclic aromatic compound Mutagen Ketone Real time system Persistent organic pollutant Carcinogen Pyrene Aerosols Air pollution PAHs Aerosol mass spectrometry Reactor Mass spectrometry Organic compounds Heterogeneous reaction Successive reaction
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Snippet	The heterogeneous reactions of typical polycyclic aromatic hydrocarbons (PAHs) and their derivatives (nitro-, oxy-, and hydroxy-PAHs) adsorbed on azelaic acid...
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SubjectTerms	Aerosols anthracenes anthraquinones Applied sciences atmospheric chemistry Atmospheric pollution containers Derivatives Exact sciences and technology free radicals gas chromatography mass spectrometry Nitration Oxygenated Pollution Polyallylamine hydrochloride Pyrenes Radicals Reaction products
Title	Nitration of particle-associated PAHs and their derivatives (nitro-, oxy-, and hydroxy-PAHs) with NO₃ radicals
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