Formation of cyclopentadienyl radical from the gas-phase pyrolysis of hydroquinone, catechol, and phenol

Environmental Science and Technology

Volumn 40, Issue 16, 2006, Pages 5071-5076

  Khachatryan, Lavrent ^a   Adounkpe, Julien ^a   Maskos, Zofia ^a   Dellinger, Barry ^a  

^a LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATECHOL; CYCLOPENTADIENYL RADICAL; GAS-PHASE PYROLYSIS; HYDROQUINONE; LOW-TEMPERATURE MATRIX ISOLATION ELECTRON PARAMAGNETIC RESONANCE (LTMI EPR);

ALCOHOLS; ANNEALING; CRYOGENICS; PARAMAGNETIC RESONANCE; PYROLYSIS; TEMPERATURE DISTRIBUTION;

ORGANOMETALLICS;

CARBON DIOXIDE; CATECHOL; CYCLOPENTADIENE DERIVATIVE; HYDROQUINONE; OXYGEN; PHENOL; RADICAL; SEMIQUINONE;

ALCOHOLS; ANNEALING; CRYOGENICS; ORGANOMETALLICS; PARAMAGNETIC RESONANCE; PYROLYSIS; TEMPERATURE DISTRIBUTION;

ANNEALING; ELECTRON SPIN RESONANCE; GAS PHASE REACTION; LOW TEMPERATURE; PHENOL; PYROLYSIS; SPECTRUM;

ARTICLE; COOLING; DEGRADATION; ELECTRON SPIN RESONANCE; GAS ANALYSIS; LOW TEMPERATURE; PYROLYSIS;

CARBON DIOXIDE; CATECHOLS; CHEMISTRY TECHNIQUES, ANALYTICAL; CHEMISTRY, ANALYTICAL; CYCLOPENTANES; ELECTRON SPIN RESONANCE SPECTROSCOPY; ENVIRONMENTAL MONITORING; EQUIPMENT DESIGN; FREE RADICALS; HYDROQUINONES; MODELS, CHEMICAL; PHENOL; PHENOLS; TEMPERATURE;

EID: 33747462141     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es051878z     Document Type: Article

References (59)

1. Dellinger, B.; Pryor, W. A.; Cueto, R.; Squadrito, G. L.; Hedge, V.; Deutsch, W. A. Role of free radicals in the toxicity of airborne fine particulate matter. Chem. Res. Toxicol. 2001, 14, 1371-1377.
2. Dellinger, B.; Pryer, W. A.; Cueto, R.; Squadrito, G. L.; Deutsch, W. A. Combustion-generated radicals and their role in the toxicity of fine particulate. Organohal. Comp. 2000, 46, 302-305.
3. Hirakawa, K.; Oikawa, S.; Hiraku, Y.; Hirosawa, I.; Kawanishi, S. Catechol and hydroquinone have different redox properties responsible for their differentioal DNA-damaging ability. Chem. Res. Toxicol. 2002, 15, 76-82.
4. Wooten, J. B.; Chouchane, S.; Mueller, B.; Wittig, A.; Tewes, F. J. Involvement of semiquinone radicals in the in vitro cytotoxicity of cigarette smoke tar. In International Congress on Combustion By-Products and Their Health Effects; 2005; The University of Arizona: Abstracts.
5. Pryor, W. A.; Prier, D. G.; Church, D. F. ESR Study of mainstream and sidestream cigarette smoke: Nature of free radicals in gas-phase smoke and in cigarette tar. Environ Health Perspect. 1983, 47, 345-355.
6. Church, D.; Pryor, W. Free-Radical Chemistry of Cigarette Smoke and its Toxicological Implications. Environ. Health Perspect. 1985, 64, 111-126.
7. Fessenden, E. S.; Schuler, R. H. Electron Spin Resonance Studies of Transient Alkyl Radicals. J. Chem. Phys. 1963, 39, 2147-2195.
8. Gerson, F.; Huber, W. Electron Spin Resonance Spectroscopy of Organic Radicals; Wiley-VCH: Berlin, 2003.
9. Pryor, W. A.; Stone, K.; Zang, L-Y.; Bermudez, E. Fractionation of Aqueous Cigarette Tar Extracts: Fractions that Contain the Tar Radical Cause DNA Damage. Chem. Res. Toxicol. 1998, 11, 441-448.
10. Squadrito, G. L.; Cueto, R.; Dellinger, B.; Pryor, W. A. Quinoid redox cycling as a mechanism for sustained free radical generation by inhaled airborne paniculate matter. Free Radical Biol. Med. 2001, 31, 1132-1138.
11. Roemer, E.; Stabbert, R.; Rustemeier, K.; Veltel, D. J.; Meisgen, T. J.; Reininghaus, W.; Carchman, R. A.; Gaworski, C. L.; Podraza, K. F. Chemical composition, cytotoxicity and mutagenicity of smoke from US commercial and reference cigarettes smoked under two sets of machine. Toxicology 2004, 195, 31-52.
12. Schlotzhauer, W. S.; Martin, R. M.; Snook, M. E.; Williamson, R. E. Pyrolytic studies on the contribution of tobacco leaf constituents to the formation of smoke catechols. J. Agric. Food Chem. 1982, 30, 372-374.
13. Carmella, S. G.; Hecht, S. S.; Tso, T. C.; Hoffmann, D. Roles of tobacco cellulose, sugars, and chlorogenic acid as precursors to catechol in cigarette smoke. J. Agric. Food Chem. 1984, 32, 267-273.
14. Counts, M. E.; Morton, M. J.; Laffoon, S.W.; Cox, R. H.; Lipowicz, P. J. Smoke composition and predicting relationships for international commercial cigarettes smoked with three machine smoking conditions. Regul. Toxicol. Pharmacol. 2005, 41, 185-227.
15. Dorrestijn, E.; Laarhoven, L. J. J.; Arends, I. W. C. E.; Mulder, P. The occurrence and reactivity of phenoxyl linkages in lignin and low rank coal. J. Anal. Appl. Pyrol. 2000, 54, 153-192.
16. Sakai, T.; Hattori, M. Thermal Decomposition of Catechol, Hydroquinone and Resorcinol. Chem. Lett. 1976, 1153-1156.
17. Wornat, M. J.; Ledesma, E. B.; Marsh, N. D. Polycyclic aromatic hydocarbons from the pyrolysis of catechol (ortho-dihdroxy-benzene), a model fuel representative of entities in tobacco, coal, and lignin. Fuel 2001, 80, 1711-1726.
18. Ledesma, E. B.; Marsh, N. D.; Sandrowitz, A. K.; Wornat, M. J. Global Kinetic Rate Parameters for the Formation of Polycyclic Aromatic Hydrocarbons [PAH] form the Pyrolysis of Catechol, A Model Compound Representative of Solid Fuel Moieties. Energy Fuels 2002, 16 (6), 1331-1336.
19. Marsh, N. D.; Ledesma, E. B.; Sandrowitz, A. K.; Wornat, M. J. Yields of Polycyclic Aromatic Hydrocarbons from the Pyrolysis of Catechol [ortho-Dihydroxybenzene]: Temprature and Residence Time Effects. Energy Fuels 2004, 18 (1), 209-217.
20. Ledesma, E. B.; Marsh, N. D.; Sandrowitz, A. K.; Wornat, M. J. An Experimental Study on the Thermal Decomposition of Catechol. Proc. Combust. Inst. 2002, 29, 2299-2306.
21. Shin, E.-J.; Hajaligol, M. R.; Rasouli, F. Heterogeneous cracking of catechol under partially oxidative conditions. Fuel 2004, 83, 1445-1453.
22. C. Puglisi, L. S.; Montaudo, G. Thermal Decomposition Processes in Aromatic Polycarbonates Ivestigated by Mass Spectrometry. Macromolecules 1999, 32, 2194-2203.
23. Vitalini, D. S. E.; Maravigna, P. Selective Formation of Cyclic Monomer, Dimer, or Trimer in the Pyrolysis of Isomeric DIhydroxybenzene Phthalate Polyesters. Macromolecules 1994, 27(8), 2291-2296.
24. Zang, L. Y.; Stone, K.; Pryor, W. A. Detection of Free Radicals in Aqeous Extracts of Cigarette Tar by ESR. Free Radical Biol. Med. 1995, 19, 161-167.
25. Nalbandyan, A. B.; Mantashyan, A. H. The Elementary Processes in Slow Gas-Phase Reactions; Inst. Chem. Phys. NA of Armenia: Yerevan, Armenia, 1975.
26. Carlier, M.; Sochet, L.-R. Detection of free radicals in the gas-phase oxidation and combustion reactions of hydrocarbons by EPR. C. R. Acad. Sci. Ser. C 1970, 271, 114-117.
27. Carlier, M.; Pauwels, J. P.; Sochet, L.-R. Application of ESR techniques to the study of gas-phase oxidation and combustion phenomena. Oxid. Commun. 1984, 6, 141-156.
28. Davidson, I. M. T.; Ellis, A. M.; Mills, G. P.; Pennington, M.; Povey, I. M.; Raynor, J. B.; Russell, D. K.; Saydam, S.; Workman, A. D. Mechanism of pyrolysis of organometallic deposition precursors. J. Mater. Chem. 1994, 4, 13.
29. Mach, K.; Mills, G. P.; Raynor, J. B. Low-pressure pyrolysis of hexamethyldisilane: ESR identification of radical intermediates. J. Organomet. Chem. 1997, 532, 229-233.
30. 2 during the gas-phase oxidation of methane. Int. J. Chem. Kinet. 1982, 14, 1231-1241.
31. Mantashyan, A. A.; Khachatryan, L. A.; Niazyan, O. M.; Arsentiev, S. D. On the reactions of peroxy radicals in the process of slow combustion of methane and ethylene. Combust. Flame 1981, 43, 221.
32. Ingram, D. J. E. Free radicals as studied by Electron Spin Resonance; Butterworth: London, 1958; p 210.
33. Mile, B. Free radical studies at low temperatures. Angew. Chem., Int. Ed. 1968, 7, 507-519.
34. Delhaes, P.; Marchand, A.A. Analize de la forme et de la position de signaux RPE observes sur des carbons graphitiques pulverulents. Carbon 1968, 6, 257.
35. Szent-Gyorgyi, A.; Isenberg, I.; Baird, S. On the electron donating properties of carcinogens. Proc. Natl. Acad. Sci., U.S.A. 1960, 46, 1444.
36. Kasai, P. H.; Clark, P. A.; Whipple, E. B. The electronic ground states of aryl radicals. J. Am. Chem. Soc. 1969, 92, 2640-2644.
37. Barclay, L. R. C.; Cromwell, G. R.; Hilborn, J. W. Photochemistry of a model lignin comound. Spin trapping of primary products and properties of an oligomer. Can. J. Chem. 1994, 72, 35-41.
38. Neta, P.; Fessenden, R. W. Hydroxyl radical reactions with phenols and anilines as studied by ESR. J. Phys. Chem. 1974, 78, 523-529.
39. Graf, F.; Loth, K.; Gunthard, H.-H. Chlorine hyperfine splittings and spin density distribution of peroxy radicals. An ESR and Quantum chemical study. Helv. Chim. Acta 1977, 60, 710-721.
40. Allard, P.; Barra, A. L.; Andersson, K. K.; Schmidt, P. P.; Atta, M.; Graslund, A. Characterization of a new tyrosyl free radical in Salmonella typhimurium ribonucleotide reductase with EPR at 9.45 and 245 GHz. J. Am. Chem. Soc. 1996, 118, 895-896.
41. Hales, B. J. Immobilized Radicals. I. Principal Electron Spin Resonance Parameters of the Benzosemiquinone Radical. J. Am. Chem. Soc. 1975, 97, 5993-5997.
42. 5. J. Chem. Phys. 1965, 42, 3931-3934.
43. Omnishi, S.-I.; Nitta, I. EPR Study of Free Radicals Produced in Irradiated Cyclopentadiene and Cyclohexene: The Cyclopentadienyl and Cyclohexenyl Radicals. J. Chem. Phys. 1963, 39, 2848-2849.
44. Barker, P. J.; Davies, A. G.; Tse, M.-W. The photolysis of cyclopentadienyl compounds of tin and mercury. ESR spectra and electronic configuration of the cyclopentadienyl, deuteriocyclopentadienyl, and alkylcyclopentadienyl radicals. J. Chem. Soc., Perkin Trans. 2 1980, 941-948.
45. Linder, R. E.; Ling, A. C. Structure of radicals produced by gamma- radiolysis. Part 2. Radicals derived from five-membered alycyclic molecules. Can. J. Chem. 1972, 50, 3982-3987.
46. 13C hyperfine coupling constant of cyclopentadienyl radicals as studied by ESR. J. Am. Chem. Soc. 1980, 102, 5202-5207.
47. Liu, A.; Potsch, S.; Davydov, A.; Barra, A.-I.; Rubin, H.; Graslund, A. The tyrosyl free radical of recombinant ribonucleotide reductase from mycobacterium tuberculosis is located in a rigid hydrophobic pocket. Biochemistry 1998, 37, 16369-16377.
48. Cypres, R.; Bettens, B. La formation de la plupart des composes aromatiques produits lors de la pyrolyse du phenol, ne fait pas intervenir le carbone porteur de la fonction hydroxyle. Tetrahedron 1975, 31, 359.
49. Cypres, R.; Bettens, B. Mecanismes de fragmentation pyrolitique du phenol et des cresols. Tetrahedron 1974, 30, 1253
50. Lin, C.-Y.; Lin, M. C. Unimolecular decomposition of the phenoxy radical in shock waves. Int. J. Chem. Kinet. 1985, 17, 1025-1028.
51. Lovell, A. B.; Brezinsky, K.; Glassman, I. The gas-phase pyrolysis of phenol. Int. J. Chem. Kinet. 1989, 21, 547-560.
52. Cooke, S.; Lares, M. M. Destruction of environmentally hazardous monochlorinated phenols via pyrolysis in an inert atmosphere. Carbon 1994, 32, 1055-1058.
53. Brezinsky, K.; Pecullan, M.; Glassman, I. Pyrolysis and oxidation of phenol. J. Phys. Chem. A 1998, 102, 8614-8619.
54. Evans, C. E.; Dellinger, B. Mechanisms of Dioxin Formation from the High-Temperature Pyrolysis of 2-Chlorophenol. Environ. Sci. Technol. 2003, 37, 1325-1330.
55. He, Y. Z.; Mallard, W. G.; Tsang, W. Kinetics of hydrogen and hydroxyl radical attack on phenol at high temperatures. J. Phys. Chem. 1988, 92, 2196.
56. Baulch, D. L.; Cobos, C. J.; Cox, R. A.; Esser, C.; Frank, P.; Just, Th.; Kerr, J. A.; Pilling, M. J.; Troe, J.; Walker, R. W.; Warnatz, J. Evaluated kinetic data for combustion modelling. J. Phys. Chem. Ref. Data 1992, 21, 411-429.
57. 5 cyclopentadienyl moiety. Proc. Combust. Inst. 1996, 26, 685-692.
58. Mulholland, J. A.; Lu, M.; Kim, D. H. Pyrolytic growth of polycyclic aromatic hydrocarbons by clyclopentadienyl moieties. Proc. Combust. Inst. 2000, 28, 2593-2599.
59. Frenklach, M.; Schuetz, C. A.; Ping, J. Migration mechanism of aromatic-edge growth. In 30th Inernational Symposium on Combustion, Chicago; The Combustion Institute Part 1: Pittsburgh, 2004, 1389-1396.