Metallic Ca-Rh/C-methanol, a high-performing system for the hydrodechlorination/ring reduction of mono- and poly chlorinated aromatic substrates

Environmental Science and Technology

Volumn 43, Issue 15, 2009, Pages 5952-5958

  Mitoma, Yoshiharu ^a   Kakeda, Mitsunori ^a   Simion, Alina Marieta ^b   Egashira, Naoyoshi ^a   Simion, Cristian ^b  

^a PREFECTURAL UNIVERSITY OF HIROSHIMA   (Japan)

^b UNIVERSITY POLITEHNICA OF BUCHAREST   (Romania)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORINATED AROMATICS; HYDRODECHLORINATION; HYDROGEN DONOR; MAGNETIC STIRRING; METHOXY; REACTION TIME; REDUCTION CATALYST; SECONDARY REACTIONS;

AMINES; BENZENE; CALCIUM; FUNCTIONAL GROUPS; HYDROGEN; METHANOL;

AMINATION;

AMINOCHLOROBENZENE; BENZENE DERIVATIVE; CALCIUM; CHLORINATED HYDROCARBON; CHLOROBENZENE; HYDROGEN; HYDROXYLCHLOROBENZENE; METHANOL; METHOXYCHLOROBENZENE; METHYLCHLOROBENZENE; POLYCHLOROBENZENE; RHODIUM; UNCLASSIFIED DRUG;

CALCIUM; CHLOROBENZENE; DECHLORINATION; METHANOL; REACTION KINETICS; REDUCTION; SUBSTRATE; TRANSFORMATION;

ARTICLE; BIODEGRADATION; BIOTRANSFORMATION; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; DECHLORINATION; DETOXIFICATION; HYDRODECHLORINATION; MAGNETIC FIELD; REDUCTION; RING REDUCTION; SOIL POLLUTION; SUBSTITUTION REACTION;

CALCIUM; CHLORINE; CHLOROBENZENES; ENVIRONMENTAL MONITORING; ENVIRONMENTAL POLLUTANTS; HYDROGEN; MAGNETICS; METALS; METHANOL; MODELS, CHEMICAL; TEMPERATURE; TIME FACTORS;

EID: 68049126560     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es9004587     Document Type: Article

References (55)

1. Ramamoorthy, S.; Ramamoorthy, S. Chlorinated Organic Compounds in the Environment; CRC-Press: Boca Raton, FL, 1997.
2. Stringer, R.; Johnston, P. Chlorine in the Environment: An Overview of the Chlorine Industry; Kluwer Academic Publishers: Dordrecht, 2001.
3. Schmittinger, P. Chlorine: Principles and Industrial Practice; Wiley-VCH: Weinheim, 2000.
4. Henschler, D. Toxicity of chlorinated organic compounds: effects of the introduction of chlorine in organic molecules. Angew. Chem., Int. Ed. Eng. 1994, 33 (19), 1920-1935.
5. Thornton, J. Pandora's Poison: Chlorine, Health and a New Environmental Strategy; MIT Press: London, 2000.
6. Gibbs, L. M. Dying from Dioxin: A Citizen's Guide to Reclaiming Our Health and Rebuilding Democracy; South End Press: Cambridge, 1995.
7. Pollock, T. Dioxins and Furans: Questions and Answers;Academy of Natural Sciences: Philadelphia, 1989.
8. Bretthauer, E. W.; Kraus, H. W. Dioxin Perspectives: A Pilot Study on International Information Exchange on Dioxins and Related Compounds (NATO Challenges of Modern Society); Plenum Publications Corp.: New York, 1992.
9. Allen, R. The Dioxin War: Truth and Lies about a Perfect Poison; Pluto Press: London, 2004.
10. Schecter, A.; Gasiewics, T. A. Dioxin and Health; Wiley-Interscience: New York, 2003.
11. Zook, D. R., Rappe, C. Dioxins and Health-Environmental Sources, DistributionandFate of Polychlorinated Dibenzodioxins, Dibenzofurans and Related Organochlorines; Schecter, A.; Plenum: New York, 1994.
12. Robertson, L. W.; Hansen, L. G.; Roberts, L., Eds. PCBs: Recent Advances in Environmental Toxicology and Health Effects, University of Kentucky Press: Lexington, 2001; and references cited therein.
13. National Research Council of the National Academies, Health Risks from Dioxin and Related Compounds. Evaluation of the EPA Reassessment; The National Academies Press: Washington, DC, 2006 and references cited therein.
14. Alonso, F.; Beletskaya, I. P.; Yus, M. Metal-mediated reductive hydrodehalogenation of organic halides. Chem. Rev. 2002, 102, 4009-4091, and references cited therein.
15. Hall, A. K.; Harrowfield, J. M.; Hart, R. J.; McCormick, P. G. Mechanochemical reaction ofDDTwith calcium oxide. Environ. Sci. Technol. 1996, 30, 3401-3407.
16. Loiselle, S.; Barnca, M.; Mulas, G.; Cocco, G. Selective mechanochemical dehalogenation of chlorobenzenes over calcium hydride. Environ. Sci. Technol. 1997, 31, 261-266.
17. Aresta, M.; Dibenedetto, A.; Pastore, T. Mechanochemistry: An old technology with new applications to environmental issues. Decontamination of polychlorobiphenyl-contaminated soil by high-energy milling in the solid state with ternary hydrides. In Environmental Chemistry. Part VI; Lichtfouse, E., Schwarzbauer J., Robert D., Eds.; Springer: Berlin, 2005; pp 553-559.
18. Wu, T.-C.; Xiong, H.; Rieke, R. D. Organocalcium chemistry: preparation and reactions of highly reactive calcium. J. Org. Chem. 1990, 55, 5045-5051.
19. O'Brien, R. A.; Chen, T.; Rieke, R. D. Chemical modification of halogenated polystyrene resins utilizing highly reactive calcium and the formation of calcium cuprate reagents in the preparation of functionalized polymers. J. Org. Chem. 1992, 57, 2667-2677.
20. Hutchins, R. O.; Zipkin, R. E.; Taffer, I. M. Reductions of alkyl and aryl halides with magnesium and methanol. Synth. Commun. 1989, 19, 1519-1522.
21. Tundo, P.; Perosa, A.; Selva, M.; Zinovyev, S. S. A mild catalytic detoxification method for PCDDs and PCDFs. Appl. Catal., B 2001, 32, L1-L7.
22. Evdokimova, G.; Zinovyev, S. S.; Tundo, P. Selectivity issues in the catalytic multiphase reduction of functionalized halogenated aromatics over Pd/C, Pt/C, and Raney-Ni. Appl. Catal., A 2004, 271, 129-136.
23. Yuan, G.; Keane, M. A. Liquid-phase hydrodechlorination of chlorophenols over Pd/C and Pd/Al2O3: a consideration of HCl/ catalyst interactions and solution pH effects. Appl. Catal., B 2004, 52, 301-314.
24. Zinovyev, S. S.; Shinkova, N. A.; Perosa, A.; Tundo, P. Liquid phase hydrodechlorination of Dieldrin andDDTover Pd/C and Raney-Ni. Appl. Catal., B 2005, 55, 39-48.
25. Moreno, J. M.; Aramendia, M. A.; Marinas, A.; Marinas, J. M.; Urbano, F. J. Hydrodechlorination of 3-chloropyridine and chlorobenzene in methanol solution over alkali-modified zir-conia-supported palladium catalysts. Appl. Catal., B 2005, 59, 275-283.
26. Ukisu, Y.; Iimura, S.; Uchida, R. Catalytic dechlorination of polychlorinated biphenyls with carbon-supported noble metal catalysts under mild conditions. Chemosphere 1996, 33, 1523-1530.
27. Ukisu, Y.; Miyadera, T. Catalytic dechlorination of PCDD/Fs under mild conditions. Organohalogen Compd. 2001, 54, 119-122.
28. Ukisu, Y.; Miyadera, T. Dechlorination of polychlorinated dibenzo-p-dioxins catalyzed by noble metal catalysts under mild conditions. Chemosphere 2002, 46, 507-510.
29. Ukisu, Y.; Miyadera, T. Catalytic dechlorination ofPCDDs,PCDFs and co-PCBs with supported palladium catalysts. Organohalogen Compd. 2002, 56, 393-396.
30. Ukisu, Y.; Miyadera, T. Hydrogen-transfer hydrodechlorination of polychlorinated dibenzo-p-dioxins and dibenzofurans catalyzed by supported palladium catalysts. Appl. Catal., B 2003, 40, 141-149.
31. Ukisu, Y.; Miyadera, T. Dechlorination of dioxins with supported palladium catalysts in 2-propanol solution. Appl. Catal., A 2004, 271, 165-170.
32. Ukisu, Y. Highly enhanced hydrogen-transfer hydrodechlorination and hydrogenation reactions in alkaline 2-propanol/ methanol over supported palladium catalysts. Appl. Catal., A 2008, 349, 229-232.
33. Coq, B.; Ferrat, G.; Figueras, F. Gas phase conversion of chlorobenzene over supported rhodium catalysts. React. Kinet. Catal. Lett. 1985, 27 (1), 157-161.
34. Fujita, K.-I.; Owaki, M.; Yamaguchi, R. Chemoselective transfer hydrodechlorination of aryl chlorides catalyzed by Cp*Rh complexes. Chem. Commun. 2002, 2964-2965.
35. Léger, B.; Nowicki, A.; Roucoux, A.; Rolland, J.-P. Competitive hydrogenation/dehalogenation of halogenoarenes with surfactant-stabilized aqueous suspensions of rhodium and palladium colloids: a major effect of the metal nature. J. Mol. Catal. A: Chem. 2007, 266 (1-2), 221-225.
36. Mitoma, Y.; Nagashima, S.; Simion, C.; Simion, A. M.; Yamada, T.; Mimura, K.; Ishimoto, K.; Tashiro, M. Dehalogenation of aromatic halides using metallic calcium in ethanol. Environ. Sci. Technol. 2001, 35, 4145-4148.
37. Mitoma, Y.; Uda, T.; Egashira, N.; Simion, C.; Tashiro, H.; Tashiro, M.; Fan, X. Approach to highly efficient dechlorination ofPCDDs, PCDFs, and coplanar PCBs using metallic calcium in ethanol under atmospheric pressure at room temperature. Environ. Sci. Technol. 2004, 38, 1216-1220.
38. Mitoma, Y.; Takase, M.; Yoshino, Y.; Masuda, T.; Tashiro, H.; Egashira, N.; Oki, T. Novel mild hydrodechlorination of PCDDs, PCDFs, and co-PCBs inside fly ash using a calcium-promoted rhodium carbon catalyst in methanol. Environ. Chem. 2006, 3, 215-218.
39. Mitoma, Y.; Tasaka, N.; Takase, M.; Masuda, T.; Tashiro, H.; Egashira, N.; Oki, T. Calcium-promoted catalytic degradation of PCDDs, PCDFs, and coplanar PCBs under a mild wet process. Environ. Sci. Technol. 2006, 40, 1849-1854.
40. Mitoma, Y.; Egashira, N.; Simion, C. Highly effective degradation of polychlorinated biphenyls in soil mediated by a Ca/Rh bicatalytic system. Chemosphere 2009, 74, 968-973.
41. Miyazawa, A.; Saitou, K.; Tanaka, K.; Gadda, T. M.; Tashiro, M.; Surya Prakash, G. K.; Olah, G. A. Reaction of primary amines with Pt/C catalyst in water under microwave irradiation: a convenient synthesis of secondary amines from primary amines. Tetrahedron Lett. 2006, 47, 1437-1439.
42. Hung, L.-S.; Ingram, L. L., Jr. Effect of solvents on the photodegradation rates of octachlorodibenzo- p-dioxin. Bull. Environ. Contam. Toxicol. 1990, 44, 380-386.
43. Wagenaar, W. J.; Boelhouwers, E. J.; de Kok, H. A. M.; Groen, C. P.; Govers, H. A. J.; Olie, K.; de Gerlach, J; de Rooij, C. G. A comprehensive study of the photolytic degradation of octachlorodibenzofuran (OCDF) and octachlorodibenzo-p-dioxin (OCDD). Chemosphere 1995, 31, 2983-2992.
44. Fueno, H.; Tanaka, K.; Sugawa, S. Theoretical study of the dechlorination reaction pathways of octachlorodibenzo-p-dioxin. Chemosphere 2002, 48, 771-778.
45. Schoonenboom, M. H.; Zoetemeijer, H. E.; Olie, K. Dechlorination of octachlorodibenzo-p-dioxin and octachlorodibenzofuran on an alumina support. Appl. Catal., B 1995, 6, 11-20.
46. Konstantinov, A.; Bunce, N. J. Photodechlorination of octachlorodibenzo-p-dioxin and octachlorodibenzofuran in alkane solvents in the absence and presence of triethylamine. J. Photochem. Photobiol. A.: Chem. 1996, 94, 27-35.
47. Bartak, P.; Cap, L. Determination of phenols by solid-phase microextraction. J. Chromatogr., A 1997, 767, 171-175.
48. Dentel, S. K; Bottero, J. Y; Khatib, K; Demougeot, H; Duguet, J. P; Anselme, C. Sorption of tannic acid, phenol, and 2,4,5-trichlorophenol on organoclays. Water Res. 1995, 29, 1273-280.
49. Wang, X. P.; Shan, X. Q.; Luo, L.; Zhang, S. Z.; Wen, B. Sorption of 2,4,6-trichlorophenol in model humic acid-clay systems. J. Agric. Food Chem. 2005, 53, 3548-3555.
50. Walborsky, H. M.; Hamdouchi, C. Mechanism of organocalcium reagent formation. J. Org. Chem. 1993, 58, 1187-1193.
51. Benkeser, R. A.; Belmonte, F. G.; Kang, J. A new reducing system: calcium metal in amines. Reduction of aromatic hydrocarbons. J. Org. Chem. 1983, 48, 2796-2802.
52. Benkeser, R. A.; Laugal, J. A.; Rappa, A. A safe and convenient new procedure for reducing aromatic compounds to Birch-type products. Tetrahedron Lett. 1984, 25 (20), 2089-2092.
53. Saeki, S.; Kano, J.; Saito, F.; Shimme, K.; Masuda, S.; Inoue, T. Effect of additives on dechlorination of PVC by mechanochemical treatment. J. Mater. Cycles Waste Manag. 2001, 3, 20-23.
54. Koper, O.; Klabunde, K. J. Destructive adsorption of chlorinated hydrocarbonsonultrafine (nanoscale) particles of calcium oxide. 3. Chloroform, trichloroethene, and tetrachloroethene. Chem. Mater. 1997, 9, 2481-2485.
55. Allal, K. M.; Dolignier, J.-C.; Martin, G. Reaction mechanism of calcium hydroxide with gaseous hydrogen chloride. Revue Inst. Fr. Pet. 1998, 53, 871-880.