Atmospheric fate of a series of furanaldehydes by their NO3 reactions

Abstract The kinetics of the reactions of the NO3 radical with 2-furanaldehyde, 3-furanaldehyde and 5-methyl-2-furanaldehyde have been measured at 298 ± 2 K and 760 Torr of total pressure using a relative kinetic method. The simultaneous losses of furanaldehydes and a reference compound were followed by FTIR spectroscopy. The rate constants obtained for the NO3 reactions are (in cm3 molecule−1 s−1): (1.20 ± 0.28) × 10−12 for 2-furanaldehyde, (3.41 ± 0.79) × 10−12 for 3-furanaldehyde and (5.51 ± 1.27) × 10−12 for 5-methyl-2-furanaldehyde. This study is the first determination of the rate constants for the reaction of NO3 radicals with furanaldehydes. The results are presented and discussed in terms of structure-reactivity relationships. Calculated atmospheric lifetimes reveal that the night-time reaction with the nitrate radical is the most important loss process for these kinds of compounds.

[1]  J. Burrows,et al.  Peroxy radicals from night-time reaction of N03 with organic compounds , 1990, Nature.

[2]  I. Barnes,et al.  Product and kinetic study of the oh-initiated gas-phase oxidation of Furan, 2-methylfuran and furanaldehydes at ≈ 300 K , 1995 .

[3]  J. Arey,et al.  Kinetics of the gas-phase reactions of NO3 radicals and O3 with 3-methylfuran and the OH radical yield from the O3 reaction , 1996 .

[4]  I. Barnes,et al.  Rate coefficients for the gas-phase reactions of hydroxyl radicals with furan, 2-methylfuran, 2-ethylfuran and 2,5-dimethylfuran at 300 ± 2 K , 1992 .

[5]  J. Burrows,et al.  The nitrate radical: Physics, chemistry, and the atmosphere , 1991 .

[6]  S. M. Aschmann,et al.  Rate constants for the gas-phase reactions of the nitrate radical with a series of organic compounds at 296 .+-. 2 K , 1988 .

[7]  U. Platt,et al.  Observation and role of the free radicals NO3, ClO, BrO and IO in the troposphere , 1995 .

[8]  W. Carter,et al.  Rate constants for the gas-phase reactions of nitrate radicals with furan, thiophene, and pyrrole at 295 .+-. 1 K and atmospheric pressure , 1985 .

[9]  E. Jiménez,et al.  Daytime tropospheric loss of hexanal and trans-2-hexenal: OH kinetics and UV photolysis , 2006 .

[10]  B. Finlayson‐Pitts,et al.  Unexpectedly high concentrations of molecular chlorine in coastal air , 1998, Nature.

[11]  G. Buchbauer,et al.  Volatile compounds of shea butter samples made under different production conditions in western, central and eastern Africa , 2009 .

[12]  I. Barnes,et al.  Rate constants of the Br-initiated gas-phase oxidation of a series of alcohols, furans and benzenes at 300±2 K , 1999 .

[13]  B. Cabañas,et al.  Atmospheric degradation of 3-methylfuran: kinetic and products study , 2010 .

[14]  W. Rolle†,et al.  Gas-phase rate constants for the reaction of NO3 radicals with furan and methyl-substituted furans , 1996 .

[15]  S. M. Aschmann,et al.  Kinetics of the reactions of OH radicals with 2- and 3-methylfuran, 2,3- and 2,5-dimethylfuran, and E- and Z-3-hexene-2,5-dione, and products of OH + 2,5-dimethylfuran. , 2011, Environmental science & technology.

[16]  Roger Atkinson,et al.  Gas-phase tropospheric chemistry of biogenic volatile organic compounds: a review , 2003 .

[17]  W. Carter Development of Ozone Reactivity Scales for Volatile Organic Compounds , 1994 .

[18]  W. Carter,et al.  Kinetics of the reactions of O3 and OH radicals with furan and thiophene at 298 ± 2 K , 1983 .

[19]  Philippe Schmitt-Kopplin,et al.  Physico-chemical characterization of SOA derived from catechol and guaiacol – a model substance for the aromatic fraction of atmospheric HULIS , 2011 .

[20]  B. Cabañas,et al.  Study of reaction processes of furan and some furan derivatives initiated by Cl atoms , 2005 .

[21]  B. Cabañas,et al.  Oxidation of heterocycles in the atmosphere: Kinetic study of their reactions with NO3 radical , 2004 .

[22]  E. Monedero,et al.  Kinetic study of 2‐furanaldehyde, 3‐furanaldehyde, and 5‐methyl‐2‐furanaldehyde reactions initiated by Cl atoms , 2008 .

[23]  B. Cabañas,et al.  An Experimental Study on the Temperature Dependence for the Gas-Phase Reactions of NO3 Radical with a Series of Aliphatic Aldehydes , 2001 .

[24]  B. Cabañas,et al.  Absolute Rate Coefficients for the Gas-Phase Reactions of NO3 Radical with a Series of Monoterpenes at T = 298 to 433 K , 1999 .

[25]  W. Hao,et al.  The Tropical Forest and Fire Emissions Experiment: overview and airborne fire emission factor measurements , 2007 .

[26]  W. Carter,et al.  Rate constants for the gas-phase reactions of nitrate radicals with a series of organics in air at 298 .+-. 1 K , 1984 .

[27]  Maria Kanakidou,et al.  Tetrachloroethylene as an indicator of low Cl atom concentrations in the troposphere , 1996 .

[28]  R. Atkinson,et al.  Atmospheric lifetimes and fates of a series of sesquiterpenes , 1995 .

[29]  T. Shibamoto,et al.  Role of roasting conditions in the profile of volatile flavor chemicals formed from coffee beans. , 2009, Journal of agricultural and food chemistry.

[30]  R. Atkinson Kinetics and Mechanisms of the Gas‐Phase Reactions of the NO3 Radical with Organic Compounds , 1991 .

[31]  S. Langer,et al.  Reactions of acrolein, crotonaldehyde and pivalaldehyde with Cl atoms: structure–activity relationship and comparison with OH and NO3 reactions , 2001 .

[32]  Y. Maeda,et al.  Henry's law constants for C2–C3 fluorinated alcohols and their wet deposition in the atmosphere , 2003 .

[33]  Alan W Gertler,et al.  Measurements of Dioxin and Furan Emission Factors from Heavy-Duty Diesel Vehicles. , 1998, Journal of the Air & Waste Management Association.

[34]  I. Bejan,et al.  Atmospheric degradation of alkylfurans with chlorine atoms: Product and mechanistic study , 2009 .

[35]  M. K. Kubo,et al.  Hydrocarbon and halocarbon measurements as photochemical and dynamical indicators of atmospheric hydroxyl, atomic chlorine, and vertical mixing obtained during Lagrangian flights , 1996 .

[36]  B. d'Anna,et al.  Kinetic study of the vapour-phase reaction between aliphatic aldehydes and the nitrate radical , 1997 .

[37]  D. Shallcross,et al.  Kinetics of the gas-phase reactions of OH and NO3 radicals with aromatic aldehydes , 2005 .

[38]  P. Fraser,et al.  Global average concentration and trend for hydroxyl radicals deduced from ALE/GAGE trichloroethane (methyl chloroform) data for 1978–1990 , 1992 .

[39]  R. Atkinson Kinetics and mechanisms of the gas-phase reactions of the hydroxyl radical with organic compounds , 1989 .

[40]  G. Trystram,et al.  The fate of furfurals and other volatile markers during the baking process of a model cookie , 2008 .

[41]  A. Cecinato,et al.  DETERMINATION OF VOLATILE ORGANIC COMPOUNDS (VOC) EMITTED FROM BIOMASS BURNING OF MEDITERRANEAN VEGETATION SPECIES BY GC-MS , 2001 .

[42]  T. Wallington,et al.  Atmospheric chemistry of benzaldehyde: UV absorption spectrum and reaction kinetics and mechanisms of the C6H5C(O)O2 radical , 1999 .