Reduction of benzo[a]pyrene with acid-activated magnesium metal in ethanol: A possible application for environmental remediation

Journal of Hazardous Materials

Volumn 203-204, Issue , 2012, Pages 77-85

  Elie, Marc R ^a   Clausen, Christian A ^a   Geiger, Cherie L ^a  

^a UNIVERSITY OF CENTRAL FLORIDA   (United States)

Author keywords

Benzo a pyrene; Ethanol; Magnesium; Polycyclic aromatic hydrocarbons; Reduction

Indexed keywords

ALTERNATIVE PROCESS; AMBIENT CONDITIONS; BALL-MILLED; BENZO [A] PYRENE; CATALYTIC HYDROGENATION; COMBINED PROCESS; CONTAMINATED SOILS; ELECTRON TRANSFER; ENVIRONMENTAL HEALTH; ENVIRONMENTAL REMEDIATION; LONG-TERM EFFECTS; MAGNESIUM METAL; PARTIAL REDUCTION; PERSISTENT ORGANIC POLLUTANTS; POLYCYCLIC AROMATICS; POLYCYCLIC COMPOUNDS; REACTION MIXTURE; REDUCING SYSTEMS; REDUCTION REACTION;

ACETIC ACID; ANOXIC SEDIMENTS; AROMATIC COMPOUNDS; DEGRADATION; ETHANOL; HEALTH RISKS; HYDROCARBONS; HYDROGENATION; MAGNESIUM; MAGNESIUM POWDER; ORGANIC POLLUTANTS; PH; POLYCYCLIC AROMATIC HYDROCARBONS; REACTION RATES; REDUCTION; REMEDIATION; SOIL POLLUTION; TOXIC MATERIALS;

ORGANIC SOLVENTS;

ACETIC ACID; ALCOHOL; BENZO[A]PYRENE; MAGNESIUM; POLYCYCLIC AROMATIC HYDROCARBON;

ACETIC ACID; CATALYSIS; DEGRADATION; ENVIRONMENTAL STRESS; ETHANOL; MAGNESIUM; ORGANIC POLLUTANT; PAH; PUBLIC HEALTH; PYRENE; REMEDIATION; SEDIMENT POLLUTION; SOIL POLLUTION; SOIL REMEDIATION; TOXIC MATERIAL;

ARTICLE; CATALYSIS; ECOSYSTEM RESTORATION; ELECTRON TRANSPORT; ENVIRONMENTAL TEMPERATURE; HYDROGENATION; PROTON TRANSPORT; REDUCTION; SOIL POLLUTION;

ACIDS; BENZO(A)PYRENE; ENVIRONMENTAL REMEDIATION; ETHANOL; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MAGNESIUM;

EID: 84855712811     PISSN: 03043894     EISSN: 18733336     Source Type: Journal    
DOI: 10.1016/j.jhazmat.2011.11.089     Document Type: Article

References (59)

1. Polycyclic Aromatic Hydrocarbons: Pollution, Health Effects and Chemistry 2009, Nova Science Publishers, New York. P.A. Haines, M.D. Hendrickson (Eds.).
2. M. Mumtaz, J. George, Toxicological Profile for Polycyclic aromatic Hydrocarbons, U.S. Department of Health and Human Services, Agency for Toxic Substances and Disease Registry, 1995.
3. R. Eisler, Polycyclic Aromatic Hydrocarbon Hazards to Fish, Wildlife, and Invertebrates: A Synoptic Review, vol. 11, Fish and Wildlife Service, U.S. Department of the Interior, 1987.
4. Neff J.M. Polycyclic Aromatic Hydrocarbons in the Aquatic Environment. Source, Fate and Biological effects 1979, Applied Science Publishers, London.
5. W.H.O., Environmental Health Criteria 202: Selected Non-heterocyclic Polycyclic Aromatic Hydrocarbons. World Health Organization, Geneva, 1998, p. 883.
6. Xue W., Warshawsky D. Metabolic activation of polycyclic and heterocyclic aromatic hydrocarbons and DNA damage: a review. Toxicol. Appl. Pharmacol. 2005, 206:73-93.
7. Marie C., Maitre A., Douki T., Gateau M., Tarantini A., Guirand P., Favier A., Ravanat J.L Influence of the metabolic properties of human cells on the kinetic of formation of the major benzo[a]pyrene DNA adducts. J. Appl. Toxicol. 2008, 28:579-590.
8. Wild S.R., Jones K.C. Polynuclear aromatic hydrocarbons in the United Kingdom environment: a preliminary source inventory and budget. Environ. Pollut. 1995, 88:91-108.
9. Gan S., Lau E.V., Ng H.K Remediation of soils contaminated with polycyclic aromatic hydrocarbons (PAHs). J. Hazard. Mater. 2009, 172:532-549.
10. Lundstedt S., White P.A., Lemieux C.L., Lynes K.D., Lambert I.B., Oberg L., Hanglund P., Tysklind M. Sources, fate, and toxic hazards of oxygenated polycyclic aromatic hydrocarbons (PAHs) at PAH-contaminated sites. Ambio 2007, 36:475-485.
11. Nelkenbaum E., Dror I., Berkowitz B. Reductive hydrogenation of polycyclic aromatic hydrocarbons catalyzed by metalloporphyrins. Chemosphere 2007, 68:210-217.
12. Yuan T., Fournier A.R., Proudlock R., Marshall W.D. Continuous catalytic hydrogenation of polyaromatic hydrocarbon compounds in hydrogen-supercritical carbon dioxide. Environ. Sci. Technol. 2007, 41:1983-1988.
13. Schuth C., Reinhard M. Hydrodechlorination and hydrogenation of aromatic compounds over palladium on alumina in hydrogen saturated water. Appl. Catal. B: Environ. 1998, 18:215-221.
14. 3 under mild conditions. J. Hazard. Mater. 2005, 126:149-157.
15. Liao W., Liu H.-W., Chen H.-J., Chang W.-Y., Chiu K.-H., Wai C.M. Catalytic hydrogenation rate of polycyclic aromatic hydrocarbons in supercritical carbon dioxide containing polymer-stabilized palladium nanoparticles. Chemosphere 2011, 83:573-580.
16. 3. J. Hazard. Mater. 2002, 92:51-62.
17. Costanzo M., Patel M., Petersen K.A., Vogt P.F. Ammonium-free Birch reduction with sodium stabilized in silica gel, Na-SG (I). Tetrahedron Lett. 2009, 50:5463-5466.
18. Garst M.E., Dolby L.J., Esfandiari S., Fedoruk N.A., Chamberlain N.C., Avery A.A. Reduction with lithium in low molecular weight amines and ethylenediamine. J. Org. Chem. 2000, 65:7098-7104.
19. Lee G.H., Youn I.K., Choi E.B., Lee H.K., Yon G.H., Yang H.C., Pak C.S. Magnesium in methanol (Mg/MeOH) in organic syntheses. Curr. Org. Chem. 2004, 8:1263-1287.
20. Hutchins R.O., Suchismita, Zipkin R.E., Taffer I.M. Reductions of alkyl and aryl halides with magnesium and methanol. Synth. Commun. 1989, 19:1519-1522.
21. Bryce-Smith D., Wakefield B.J., Blues E.T. A convenient new method for the reduction of organic halides. Proc. Chem. Soc. 1963, 219.
22. Hutchins R.O., Suchismita, Zipkin R.E., Taffer I.M., Sivakumar R., Monaghan A., Elisseou E.M. Selective reductions of conjugated acetylenes with magnesium in methanol and methanol-D. Tetrahedron Lett. 1989, 30:55-56.
23. Profitt J.A., Ong H.H. Reduction of diphenylethylenes and related compounds with magnesium in methanol. J. Org. Chem. 1970, 44:3972-3974.
24. Grover P.L Pathways involved in the metabolism and activation of polycyclic aromatic hydrocarbons. Xenobiotica 1986, 16:915-931.
25. Naphthalene MSDS, 2004, naphthalene, 1,2,3,4-tetrahydro MSDS, 2004, http://www.jtbaker.com/msds/englishhtml/t1313.htm.
26. Keirstead K. The reduction of aromatic nitro compounds by magnesium and methyl alcohol. Can. J. Chem. 1953, 31:1064-1077.
27. Grosjean M-H., Zidoune M., Huot J-Y., Roue L. Hydrogen generation via alcoholysis reaction using ball-milled Mg-based materials. Int. J. Hydrogen Energy 2006, 31:1159-1163.
28. Khoudadoust A.P., Bagchi R., Suidan M.T., Brenner R.C., Sellers N.G. Removal of PAHs from highly contaminated soils found at prior manufactured gas operations. J. Hazard. Mater. 2000, B80:159-174.
29. Lee B.D., Hosomi M. Ethanol washing of PAH-contaminated soil and Fenton oxidation of washing solution. J. Mater. Cycles Waste Manag. 2000, 2:24-30.
30. Lundstedt S., Persson Y., Oberg L. Transformation of PAHs during ethanol-Fenton treatment of an aged gasworks' soil. Chemosphere 2006, 65:1288-1294.
31. Lee P.H., Ong S.K., Goldchin J., Nelson G.L. Use of solvents to enhance PAH biodegradation of coal-tar contaminated soils. Water Res. 2001, 35:3939-3941.
32. Turova N.Y., Turevskaya E.P., Kessler V.G., Yanovskaya M.I. The Chemistry of Metal Alkoxides 2002, Kluwer Academic Publishers, Massachusetts.
33. 2. Zeitschrift für anorganische und allgemeine Chemie 1968, 356:132-139.
34. Hawke D.L., Hillis J.E. Corrosion behavior. Magnesium and Magnesium Alloys 1999, 199. ASM International, Ohio, (ASM specialty handbook). M.M. Avedian, H. Baker (Eds.).
35. Tilstam U., Weinmann H. Activation of Mg metal for safe formation of Grignard reagents on plant scale. Org. Process Res. Dev. 2002, 6:906-910.
36. Taub I.A., Roberts W., LaGambina S., Kustin K. Mechanism of dihydrogen formation in the magnesium-water reaction. J. Phys. Chem. A 2002, 106:8070-8078.
37. Lee G.H., Lee H.K., Choi E.B., Kim B.T., Pak C.S. An efficient Julia olefination mediated by magnesium in ethanol. Tetrahedron Lett. 1995, 36:5607-5608.
38. Hacias K.J. Acid cleaning. Surface Cleaning, Finishing and Coating, ASM Metals Handbook 1994, vol. 5:48-53. ASM International, Ohio. ninth ed.
39. Chavez K.L, Hess D.W. A novel method of etching copper oxide using acetic acid. J. Electrochem. Soc. 2001, 148:640-643.
40. Ghali E. Magnesium and magnesium alloy. Uhlig's Corrosion Handbook 2011, 809-835. Wiley, New York. R.W. Revie (Ed.).
41. Immura H., Tabata S., Shigetomi N., Takesue Y., Sakata Y. Composites for hydrogen storage by mechanical grinding of graphite carbon and magnesium. J. Alloys Compd. 2002, 330-332:579-583.
42. Bouaricha S., Dodelet J.-P., Guay D., Huot J., Schulz R. Study of activation process of Mg-based hydrogen storage materials modified by graphite and other carbonaceous compounds. J. Mater. Res. 2001, 16:2893-2905.
43. Joseph J., Singh S.C., Gupta V.K. Morphology controlled magnesium ethoxide: influence of reaction parameters and magnesium characteristics. Part. Sci. Technol. 2009, 27:528-541.
44. Sims P., Grover P.L., Swaisland A., Pal K., Hewer A. Metabolic activation of benzo(a)pyrene proceeds by a diol-epoxide. Nature 1974, 252:326-328.
45. Graslund A., Jernstrom B. DNA-carcinogen interaction: covalent DNA-adducts of benzo(a)pyrene 7,8-dihydrodiol 9,10-epoxides studied by biochemical and biophysical techniques. Q. Rev. Biophys. 1989, 22:1-37.
46. Luch A. The Carcinogenic Effects of Polycyclic Aromatic Hydrocarbons 2005, Imperial College, London, pp. 19-96.
47. Baird W.M, Hooven L.A., Mahadevan B. Carcinogenic polycyclic aromatic hydrocarbon-DNA adducts and mechanism of action. Environ. Mol. Mutagen. 2005, 45:106-114.
48. Fu P.P., Lee H.M., Harvey R.G. Regioselective catalytic hydrogenation of polycyclic aromatic hydrocarbons under mild conditions. J. Org. Chem. 1980, 45:2797-2803.
49. Zidoune M., Grosjean M.-H., Roue L., Huot J., Schulz R. Comparative study on the corrosion behavior of milled and unmilled magnesium by electrochemical impedance spectroscopy. Corros. Sci. 2004, 46:3041-3055.
50. Grosjean M.-H., Zidoune M., Roue L., Huot J., Schulz R. Effect of ball milling on the corrosion resistance of magnesium in aqueous media. Electrochim. Acta 2004, 49:2461-2470.
51. Korshunov A., Heyrovský M., Bakardjieva S., Brabec L. Electrolytic processes in various degrees of dispersion. Langmuir 2007, 23:1523-1529.
52. Unwin P.J., Rusnacik M.R., Kresta S., Nelson A.E. Effect of surfactants on Cu nanoparticle surface chemistry and aggregation (# 245a). Proceedings of the American Institute of Chemical Engineers (AIChE), Annual Meeting 2006.
53. Unwin P.J., Rusnacik M.E., Kresta S.M., Nelson A.E. Effect of amine and thiol addition on the surface chemistry and agglomeration of fine Cu powders. Colloids Surf. A: Physicochem. Eng. Aspects 2008, 325:72-80.
54. Harvey R.G. Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenesis 1991, Cambridge University Press, Cambridge, England, pp. 124-126.
55. Jones R.G., Gilman H. Methods of preparation of organometallic compounds. Chem. Rev. 1954, 54:835-890.
56. Rogers R.J., Mitchell H.L., Fujiwara Y., Whitesides G.M. Kinetics of formation of alkyl Grignard reagents. Evidence for rate-determining electron transfer. J. Org. Chem. 1974, 39:857-858.
57. Baker T.A., Head-Gordon M. Modeling the charge transfer between alkali metals and polycyclic aromatic hydrocarbons using electronic structure methods. J. Phys. Chem. A 2010, 114:10326-10333.
58. Betowski L.D., Enlow M., Riddick L., Aue D.H. Calculation of electron affinities of polycyclic aromatic hydrocarbons and solvation energies of their radical anion. J. Phys. Chem. A 2006, 110:12927-12946.
59. March J. Advanced Organic Chemistry 2007, Wiley and Sons Inc., New York, pp. 1067-1068. seventh ed.