Articles
KOZAK V.A., GERTSIUK M.M., NEZHINA M.V., KUBASHKO A.V. ENVIRONMENTAL SAFETY AND METHODS FOR THE DETERMINATION OF POLYCYCLIC AROMATIC HYDROCARBONS. I. SOURCES OF ORIGIN AND ECOTOXIC PROPERTIES
UDC 543.544:547.68:543.272.76:574
DOI: 10.15407/zht2018.64.030
articleKOZAK V.A., GERTSIUK M.M., NEZHINA M.V., KUBASHKO A.V.
State Institution “Institute of Environmental Geochemistry National Academy of Science of Ukraine”
ENVIRONMENTAL SAFETY AND METHODS FOR THE DETERMINATION OF POLYCYCLIC AROMATIC HYDROCARBONS. I. SOURCES OF ORIGIN AND ECOTOXIC PROPERTIES
Generalize literature on basic physical and chemical properties of polycyclic aromatic hydrocarbons, their classification, features of molecular-structural characteristics and their influence on spectral and adsorption properties. Features of distribution of polycyclic aromatic hydrocarbons in natural environments, their transformation and influence on the biosphere, ways of formation of background and critically dangerous concentrations in the objects of the environment.
Key words: polycyclic aromatic hydrocarbons, physical and chemical properties, sources of origin, environment, review.
REFERENCES
1. Klar E. Politsiklicheskiye aromaticheskiye uglevodorody. M.: Khimiya, 1971, 256 s. [in Russ.]
2. Sander L.C. and Wise S.A. NIST Special Publication 922, Polycyclic Aromatic Hydrocarbon Structure Index
3. World Health Organization. IPCS, Environmental Health Criteria 202, Selected Non-heterocyclic Aromatic Hydrocarbons. 1998.
4. ISPAC 2003 International Society for Polycyclic Aromatic Compounds 2003. PAH structure/properties. URL: http://www.ispac.org/Links.htm
5. Atkinson R., Ary J. Atmosferna khimiya hazofaznykh politsyklichnykh aromatychnykh vuhlevodniv – utvorennya atmosfernykh mutaheniv. Environ Health Persp., 10.2307/3431940. 1994. V. 102. P. 117-126. [in Ukr.]
DOI: 10.2307/3431940
https://doi.org/10.2307/3431940
6. Peter E.T. Douben (Ed.), PAHs: An Ecotoxicological Perspective. ISBN: 978-0-471-56024-1. New York.: John Wiley and Sons Ltd. 2003. P. 47-63, 404 p.
DOI: 10.1002/0470867132
https://doi.org/10.1002/0470867132
7. Fetzer J. C. The Chemistry and Analysis of the Large Polycyclic Aromatic Hydrocarbons. Polycyclic Aromatic Compounds. New York: Wiley. 2000. V. 27 (2). P. 143-162.
DOI:10.1080/10406630701268255
https://doi.org/10.1080/10406630701268255
8. Polycyclic Aromatic Hydrocarbons – Occurrence in foods, dietary exposure and health effects. European Commission, Scientific Committee on Food. 2002, December 4. URL: http:/ ec.europa.eu/food/fs/sc/scf out153_en. Pdf
9. Dikun P. P. Vrednyye veshchestva v promyshlennosti. L.: Khimiya, 1973. T. 1, 320 s. [in Russ.]
10. Rabinovich V.A., Khavin Z.YA. Kratkiy khimicheskiy spravochnik. L.: Khimiya, 1977, 432 s. [in Russ.]
11. Svoystva organicheskikh soyedineniy: Spravochnik. Pod red. Potekhina A.A. L.: Khimiya. 1984, 520 s. [in Russ.]
12. Spravochnik po rastvorimosti. T.1, Kn.2. M.-L.: IAN SSSR, 1962, 502 s. [in Russ.]
13. Khimicheskaya entsiklopediya. Red. I.L. Knunyants. Sovetskaya entsiklopediya. M., 1988. T. 1, 623 s. [in Russ.]
14. Dmitrikov V., Larionov O., Nabivach V. Analiz PAU metodom VEZHKH. Uspekhi khimii, 1987. T. 56(4). S. 679-700. [in Russ.]
15. Shabad L. M. O tsirkulyatsii kantserogenov v okruzhayushchey crede. M. 1973, 300 s. [in Russ.]
16. Kazitsyna L. A., Kupletskaya N. B. Primeneniye UF-, IK-, YAMR- i mass-spektroskopii v organicheskoy khimii. M., Izd-vo MGU, 1979, 240 s. [in Russ.]
17. Teplitskaya T.A. Kvazilineynyye spektry lyuminestsentsii kak metod issledovaniya slozhnykh prirodnykh organicheskikh smesey. M:. Izd-vo MGU, 1971, 78 s. [in Russ.]
18. Mackay D., Shiu W.Y., Ma K.-C., Lee S.C. Handbook of Physical-Chemical Properties and Enviromental Fate for Organic Chemacals. CRC Press, 2006. Vol.1.
19. Sverdlova O.V. Elektronnyye spektry v organicheskoy khimii. L.:Khimiya, 1985, 248 s. [in Russ.]
20. Alekseyeva T. A., Teplitskaya T. A. Razrabotka printsipov opredeleniya tipa molekulyarnoy struktury neizvestnykh soyedineniy slozhnykh smesey metodami lyuminestsentnoy spektroskopii. Izv. AN SSSR, seriya fizich., 1978,. T. 42, N 3. S. 669-674. [in Russ.]
21. Alekseyeva T.A., Teplitskaya T.A. Spektrofluorimetricheskiye metody analiza aromaticheskikh uglevodorodov v prirodnykh i tekhnogennykh sredakh. L.: Gidrometeoizdat, 1981, 215 s. [in Russ.]
22. A. P. Il'nitskiy, G. A. Belitskiy, V. S. Mishchenko, N. V. Vizhnikova, R. G. Butenko. O vozmozhnoy evolyutsionnoy roli benz(a)pirena i drugikh kantserogennykh uglevodorodov. DAN SSSR, 1984. T. 274, N 1. S. 216-219. [in Russ.]
23. Florovskaya V. N. Predbiologicheskaya evolyutsiya uglerodistykh veshchestv na ranney Zemle: Geologicheskiy aspekt. M.: Knizhnyy dom «Librokom», 2012, 224 s. [in Russ.]
24. Battersby S. Space molecules point to organic origins. New Scientist, 2004. Retrieved 2009-12-11. URL: http:/ / www. newscientist. com/ article/ dn4552-space-molecules-point-to-organic-origins. Html
25. Mulas G., Malloci G., Joblin C., Toublanc D. Estimated IR and phosphorescence emission fluxes for specific polycyclic aromatic hydrocarbons in the Red Rectangle. Astronomy and Astrophysics, 2006. P. 446- 537.
DOI: 10.1051/0004-6361:20053738
https://doi.org/10.1051/0004-6361:20053738
26. Garcia-Hernandez D. A., Manchado, A., Garcia-Lario P., Stanghellini L., Villaver E., Shaw R. A., Szczerba R., Perea-Calderon J. V. Formation Of Fullerenes In H-Containing Planatary Nebulae. The Astrophysical Journal Letters, 2010-10-28, 724 p.
DOI: 10.1088/2041-8205/724/1/L39
https://doi.org/10.1088/2041-8205/724/1/L39
27. Atkinson Nancy. Buckyballs Could Be Plentiful in the Universe. Universe Today, 2010-10-27. Retrieved 2010-10-28. URL: http:/ / www. universetoday. com/ 76732/ buckyballs-could-be-plentiful-in-the-universe
28. Rovinskiy F.YA., Teplitskaya T.A., Alekseyeva T.A. Fonovyy monitoring politsiklicheskikh aromaticheskikh uglevodorodov. L.: Gidrometeoizdat, 1988, 224 s. [in Russ.]
29. Tolosa I., Bayona J.M., Albaiges J. Aliphatic and Polycyclic Aromatic Hydrocarbons and Sulfur. Oxygen Derivatives in Northwestern Mediterranean Sediments: Spatial and Temporal Variability, Fluxes, and Budgets Environ Sci Technol, 1996. V.30. P. 2495-2503.
DOI: 10.1021/es950647x
https://doi.org/10.1021/es950647x
30. World Health Organization. Polynuclear aromatic hydrocarbons indrinking water. Background Document for development of WHO Guidelines for Drinking-water Quality, 2003, [WHO/SDE/WSH/03.04/59]. URL: http://www.who.int/water_sanitation_health/dwq/ chemicals/en/index.html
31. Masih A., . Taneja A. Polycyclic aromatic hydrocarbons (PAHs) concentrations and related carcinogenic potencies in soil at a semi-arid region of India. Chemosphere, October 2006. V. 65(3). P. 449-456.
DOI: 10.1016/j.chemosphere.2006.01.062
https://doi.org/10.1016/j.chemosphere.2006.01.062
32. Seo J.S, Keum Y.S, Harada R.M, LiJ Q.X. Isolation and characterization of bacteria capable of degrading polycyclic aromatic hydrocarbons (PAHs) and organophosphorus pesticides from PAH-contaminated soil in Hilo, Hawaii. Agric Food Chem, 2007, Jul., 11, 55(4). P. 5383-5389. PMID:17552538.
DOI: 10.1021/jf0637630
https://doi.org/10.1021/jf0637630
33. Il'nitskiy A. P. Kantserogennyye uglevodorody v pochve, vode i rastitel'nosti. Kantserogeny v okruzhayushchey srede. M.: Gidrometeoizdat, 1975, S. 53-71. [in Russ.]
34. Il'nitskiy A. P., Belitskiy G. A., Shabad L. M. O kantserogennom aromaticheskom uglevodorode benz(a)pirene v vybrosakh vulkanov. Doklady AN SSSR, 1975. T. 225, N 1. S. 214-216. [in Russ.]
35. Il'nitskiy A. P., Mishchenko V. S., Shabad L. M. Prirodnyye istochniki kantserogennykh uglevodorodov. Kantserogennyye veshchestva v okruzhayushchey srede. M.: Gidrometeoizdat, 1979. S. 25-29. [in Russ.]
36. Dikun P.P. Opredeleniye politsiklicheskikh aromaticheskikh uglevodorodov. Problemy analiticheskoy khimii. M.: Nauka, 1979, N 6. S. 100-116. [in Russ.]
37. Gennadiyev A.N., Kozin I.S., Shurubor Ye.I. i dr. Dinamika zagryazneniya pochv politsiklicheskimi aromaticheskimi uglevodorodami i indikatsiya sostoyaniya pochvennykh yekosistem. Pochvovedeniye, 1990, N 1. S. 75-85. [in Russ.]
38. P.P. Dikun, I.A. Kalinina. Metodicheskiye ukazaniya po kachestvennomu i kolichestvennomu opredeleniyu kantserogennykh politsiklicheskikh aromaticheskikh uglevodorodov v produktakh slozhnogo sostava. M., 1976, 44 s. [in Russ.]
39. Shurubor Ye.I. Politsiklicheskiye aromaticheskiye uglevodorody v sisteme pochva-rasteniye rayona neftepererabotki (Permskoye Prikam'ye). Pochvovedeniye, 2000, N 12. S. 1509-1514. [in Russ.]
40. Pampanin D.M., Sydnes M.O. Polycyclic Aromatic Hydrocarbons a Constituent of Petroleum: Presence and Influence in the Aquatic Environment. In Hydrocarbon, Ed: v. Kutcherov. 2013. DOI: 10.5772/48176
https://doi.org/10.5772/48176
41. Khaustov A.P., Redina M.M. Politsiklicheskiye aromaticheskiye uglevodorody kak geokhimicheskiye markery zagryazneniya okruzhayushchey sredy. Ekspozitsiya. Neft'. Gaz. 2014, N 4(36). S.92-97. [in Russ.]
42. Stogiannidis E., Laane R. Source Characterization of Polycyclic Aromatic Hydrocarbons by Using Their Molecular Indices: An Overview of Possibilities. Reviews of Environmental Contamination and Toxicology, 2015. P. 49-133, 234 p.
DOI: 10.1007/978-3-319-10638-0_2
https://doi.org/10.1007/978-3-319-10638-0_2
43. Geier M.C., Chlebowski A.C., Truong L., Massey Simonich S.L., Anderson K.A., Tanguay R.L. Comparative developmental toxicity of a comprehensive suite of polycyclic aromatic hydrocarbons. Arch Toxicol., 2018 Feb., 92(2). P. 571-586. DOI: 10.1007/s00204-017-2068-9
https://doi.org/10.1007/s00204-017-2068-9
44. Florovskaya V.N., Teplitskaya T.A., Markhinin Ye.K., Podkletnov N.Ye. Poliyadernyye areny v produktakh vulkanicheskikh izverzheniy. Doklady AN SSSR, 1978. T. 240, N 1. S. 221-222. [in Russ.]
45. Wang. Z., Yang C., Yang Z., Sun J., Hollebone B., Brown C., Landriault M. Forensic fingerprinting and source identification of the 2009 Sarnia (Ontario) oil spill. J Environ. Monit., 2011 Nov. V. 13(11). P. 3004-3017. Epub 2011 Sep 28.
DOI: 10.1039/c1em10620a
https://doi.org/10.1039/c1em10620a
46. Parker D. S. N., Zhang F, . Seol Kim Y., Kaiser R.I, Landera A., Kislov V.V. et al. Low Temperature Formation of Naphthalene and its Role in the Synthesis of PAH in the Interstellar Medium. Proc. Nat. Acad. Sci., 2012. V. 109 (1). P. 53-58.
DOI: 10.1073/pnas.1113827108
https://doi.org/10.1073/pnas.1113827108
47. Zhang Y., Tao S., Global atmospheric emission inventory of polycyclic aromatic hydrocarbons (PAHs) for 2004. Atmospheric Environment, 2009, (43). P. 812-819.
DOI: 10.1016/j.atmosenv.2008.10.050
https://doi.org/10.1016/j.atmosenv.2008.10.050
48. M. Assad, V. V. Grushevski, O. G. Penyazkov, I. N. Tarasenko. Emission of polycyclic aromatic hydrocarbons contained in combustion products of gasoline engines. Doklady of the National Academy of Sciences of Belarus, 2018. T. 62, N 3. S. 341-346.
DOI: 10.29235/1561-8323-2018-62-3-341-346
https://doi.org/10.29235/1561-8323-2018-62-3-341-346
49. Shilina A.I. Migratsiya benz(a)pirena v okruzhayushchey srede. Kompleksnyy global'nyy monitoring zagryazneniyaokruzhayushchey prirodnoy sredy. Trudy 2-go Mezhdunarodnogo simpoziuma. L.: Gidrometeoizdat, 1982. S. 238-242. [in Russ.]
50. Lach A. Kantserogennyy effekt politsiklicheskikh aromaticheskikh uglevodorodov. London: Imperial Kolledzh Press, 2005. ISBN 1-86094-417-5. [in Russ.]
51. Li S. D., Grant L. Zdorov'ye i ekologicheskaya otsenka politsiklicheskikh aromaticheskikh uglevodorodov. Illinoys: Patoteks Park Forest Souz, 1981, 364 s. [in Russ.]
52. Yedvards N.T. Politsiklicheskiye aromaticheskiye uglevodorody (PAU) v nazemnoy okruzhayushchey srede -obzor. Kachestvo okruzhayushchey sredy, 1983, (12). S. 427-441.[in Russ.]
53. Regulation (EC) No 166/2006 of the european parliament and of the council of 18 January 2006 concerning the establishment of a European Pollutant Release and Transfer Register and amending Council Directives 91/689/EEC and 96/61/EC. Official Journal of the European Union, 10-02-2016, URL: http://data.europa.eu/eli/reg/2006/166/oj
54. U.S. EPA. Human Health Evaluation Manual, Supplemental Guidance: Standard Default Exposure Factors. Publication 9285.6-03. Washington. Office of Emergency and Remedial Response, 1991. URL: http://www.epa.gov
55. U.S. Environmental Protection Agency. Provisional Guidance for Quantitative Risk Assessment of Polycyclic Aromatic Hydrocarbons. Washington DC. Office of Research and Development, 1993. URL: //www.epa.gov
56. Opinion of the Scientific Committee on Food on the risks to human health of Polycyclic Aromatic Hydrocarbons in food. EC, SCF/CS/CNTM/PAH/29. 2002. URL: http://europe.eu.int/comm/food/fs/sc/scf/index_en.html?
57. Findings of the EFSA Data Collection on Polycyclic Aromatic Hydrocarbons in Food. EFSA/DATEX/002 (revision 1), 2008. URL: http://www.efsa.europa.eu;
58. Chen B.H., Lin Y.S. Formation of Polycyclic Aromatic Hydrocarbons during processing of duck meat. J. Agric. Food Chem., 1997. V. 45. P. 1394-1403.
DOI: 10.1021/jf9606363
https://doi.org/10.1021/jf9606363
59. Ambient Water Quality Criteria for Polynuclear Aromatic Hydrocarbons. USA Environmental Protection Agency. EPA 440/5-80-069.193. Oct. 1980. URL: //www.epa.gov
60. J. Beyer, G. Jonsson, C. Porte, M.M. Krahn, F. Ariese. Analytical methods for determining metabolites of polycyclic aromatic hydrocarbon (PAH) pollutants in fish bile: A review. Environ Toxicol Pharmacol, 2010. V. 30. P. 224-244.
DOI: 10.1016/j.etap.2010.08.004
https://doi.org/10.1016/j.etap.2010.08.004
61. Sandeep Agrawal, Amar Preet Kaur, Kanchan Taneja. A Comprehensive Review of Benzo Alpha Pyrene (B[A]P). Toxicology. Research Journal of Pharmaceutical, Biological and Chemical Sciences, ISSN: 0975-8585, 2018. V. 9(4). P. 1049-1058
62. F. Oesch, P. Bentley, M. Golan, P. Stasiecki. Metabolism of Benzo(a)pyrene by Subcellular Fractions of Rat Liver: Evidence for Similar Patterns of Cytochrome P-450 in Rough and Smooth Endoplasmic Reticulum but not in Nuclei and Plasma Membrane. Cancer research, 1985, 45(10). P. 4838-4843
63. A.I. Sotnichenko, V.A. Sukhanov, A.N. Saprin. Mikrosomal'nyy metabolizm 3,4-benzpirena. I. Uskorennoye khromatograficheskoye razdeleniye i identifikatsiya metabolitov «v potoke». Khim.-farm.zhurnal, 1985, N 12. S. 1435-1440. [in Russ.]
64. A.I. Sotnichenko, V.A. Sukhanov, A.N. Saprin. Mikrosomal'nyy metabolizm 3,4-benzpirena. II. Kolichestvennoye opredeleniye 7,8-dioksi-7,8-digidrobenzpirena. Khim.-farm. zhurnal, 1986, N 1. S. 28-32. [in Russ.]
65. A.I. Sotnichenko, A.N. Saprin. Mikrosomal'nyy metabolizm 3,4-benzpirena. III. Ogranichennyy kharakter substratno-pozitsionnoy spetsifichnosti arenepoksidazy i yeyo zavisimost' ot svoystv okislyayemoy svyati. Khim.farm. zhurnal, 1986, N 12. S. 1429-1437. [in Russ.]
66. L. Campo, F. Rossella, S. Pavanello, D. Mielzynska, E. Siwinska, L.Kapka, P. A.Bertaz,S. Fustinon. Urinary profiles to assess polycyclic aromatic hydrocarbons exposure in coke-oven workers, Toxicology Letters, 2010, 192(1). P. 72-78.
DOI: 10.1016/j.toxlet.2008.12.018
https://doi.org/10.1016/j.toxlet.2008.12.018
67. International Programme on Chemical Safety. Selected Non-heterocyclic Polycyclic Aromatic Hydrocarbons. In: Environmental Health Criteria, Series 202. World Health Organization, Geneva, Switzerland, 1998. URL: http://www.who.int/iris/handle/10665/41958
68. M. Benedetti, G. Martuccio, D. Fattorini, A. Canapa, M. Barucca, M.Nigro, F. Regoli Oxidative and modulatory effects of trace metals on metabolism of polycyclic aromatic hydrocarbons in the Antarctic fish. Trematomus bernacchii. Aquat Toxicol, 2007, 85. P. 167-175.
DOI: 10.1016/j.aquatox.2007.08.009
https://doi.org/10.1016/j.aquatox.2007.08.009
69. A. Tarantini, A. Maître, E. Lefèbvre, M. Marques, A. Rajhi, T. Douki. Polycyclic aromatic hydrocarbons in binary mixtures modulate the efficiency of benzo[a]pyrene to form DNA dducts in human cells. Toxicology, 2011, 279 (1-3). P. 36-44.
DOI: 10.1016/j.tox.2010.09.002
https://doi.org/10.1016/j.tox.2010.09.002
70. Ngandzhe Terese Ntonzi, Abara Enagu Abara, Ibe Kennet A, Nedzhi Piter Amba. Ekologicheskoye i toksikologicheskoye vozdeystviye politsiklicheskikh aromaticheskikh uglevodorodov (PAU) na okruzhayushchuyu sredu. Zhurn. nauch. publ. aspirantov i doktorantov, 2009, 8 (38). S. 98-102. URL: http://www.jurnal.org/articles/2009/ekol2.html
71. Suzdorf A.R., Morozov C.B., Kuzubova L.I. i dr. Politsiklicheskiye aromaticheskiye uglevodorody v okruzhayushchey srede - istochniki, profili i marshruty prevrashcheniy. Khimiya v interesakh ustoychivogo razvitiya, 1994. T. 2, N 2-3. S. 511-540. [in Russ.]