Active-iron-promoted hydrodehalogenation of organic halides

Applied Catalysis A: General

Volumn 313, Issue 1-2, 2006, Pages 94-100

  Moglie, Y ^a   Alonso, F ^b   Vitale, C ^a   Yus, M ^b   Radivoy, G ^a  

^a UNIVERSIDAD NACIONAL DEL SUR   (Argentina)

^b UNIVERSITY OF ALICANTE   (Spain)

Author keywords

Active iron; Hydrodehalogenation; Organic halides; Polychlorinated aromatics

Indexed keywords

DEHALOGENATION; DEHYDROGENATION; IRON COMPOUNDS; ISOTOPES; REACTION KINETICS;

ACTIVE-IRON; HYDRODEHALOGENATION; ORGANIC HALIDES; POLYCHLORINATED AROMATICS;

AROMATIC COMPOUNDS;

EID: 33748104235     PISSN: 0926860X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.apcata.2006.07.013     Document Type: Article

References (66)

1. Gribble G.W. J. Chem. Educ. 81 (2004) 1441
2. Mohn W.W., and Tiedje J.M. Microbiol. Rev. 56 (1992) 482
3. In: Hinchee R.E., Leeson A., and Semprini L. (Eds). Bioremediation of Chlorinated Solvents vol. 4 (1995), Batelle Press, Columbus, OH
4. Copley S.D. Chem. Biol. 4 (1997) 169
5. Castro C.E. Rev. Environ. Contam. Toxicol. 155 (1998) 1
6. Fetzner S. Appl. Microbiol. Biotechnol. 50 (1998) 633
7. Copley S.D. In: Barton D.H.R., Nakanishi K., Meth-Cohn O., and Poulter C.D. (Eds). Comprehensive Natural Products Chemistry (1999), Elsevier, Amsterdam 401-422
8. Wiegel J., and Wu Q. FEMS Microbiol. Ecol. 32 (2000) 1
9. Wichnak C., and Muller R. In: Klein J. (Ed). Biotechnology. 2nd ed. vol. 11b (2000), Wiley/VCH Verlag, Weinheim 241-271
10. Janssen D.B., Oppentocht J.E., and Poelarends G.J. Curr. Opin. Biotechnol. 12 (2001) 254
11. Seignez C., Vuillenium A., Adler N., and Peringer P. J. Hazard. Mater. 84 (2001) 265
12. Frimmel J., and Zdrazil M. J. Chem. Technol. Biotechnol. 63 (1995) 17
13. He J., Ritalahti K.M., Yang K.-L., Koenigsberg S.S., and Löffler F.E. Nature 424 (2003) 62
14. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis vol. 8 (1991), Pergamon Press, Oxford (Chapters 4.1, 4.5, 4.7 and 4.8)
15. Sutherland A.G. In: Katritzky A.R., Meth-Cohn O., Rees C.W., and Roberts S.M. (Eds). Comprehensive Organic Functional Group Transformations vol. 1 (1995), Pergamon Press, Oxford 1-11
16. Hudlický M. Reductions in Organic Chemistry. 2nd ed. (1996), American Chemical Society, Washington, DC (Chapter 7)
17. Alonso F., Beletskaya I., and Yus M. Chem. Rev. 102 (2002) 4009
18. In: Kónya Z., and Kukovecz A. (Eds). Appl. Catal. A: Gen. 271 1-2 (2004)
19. Rylander P. Hydrogenation Methods (1985), Academic Press, New York (Chapter 12)
20. Ghattas A., Abu-Reziq R., Avnir D., and Blum J. Green Chem. 5 (2003) 40
21. Lunin V.V., and Lokteva E.S. Russ. Chem. Bull. 45 (1996) 1519
22. Seyden-Penne J. Reductions by the Alumino- and Borohydrides in Organic Synthesis (1991), VCH, New York (Chapter 1.1)
23. Yoon N.M. Pure Appl. Chem. 68 (1996) 843
24. Imamoto I. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis vol. 8 (1991), Pergamon Press, Oxford 806
25. Fry A.J. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis vol. 8 (1991), Pergamon Press, Oxford 988-990
26. Matheson L.J., and Tratnyek P.G. Environ. Sci. Technol. 26 (1994) 2045
27. Wilson E.K. Chem. Eng. News 73 (1995) 19
28. Chuang F.-W., Larson R.A., and Wessman M.S. Environ. Sci. Technol. 29 (1995) 2460
29. Gillham R.W. In: Aral M.M. (Ed). Advances in Groundwater Pollution Control and Remediation (1996), Kluwer Academic Publishers, Dordrecht, The Netherlands 249-274
30. P.G. Tratnyek, Chem. Ind. (London) July 1 (1996) 499;
31. Roberts A.L., Totten L.A., Arnold W.A., Burris D.R., and Campbell T.I. Environ. Sci. Technol. 30 (1996) 2654 and references cited therein
32. Weber E.J. Environ. Sci. Technol. 30 (1996) 716
33. Geiger C.L., Ruiz N.E., Clausen C.A., Reinhart D.R., and Quinn J.W. Water Res. 36 (2002) 1342
34. McGuire M.M., Carlson D.L., Vikesland P.J., Kohn T., Grenier A.C., Langley L.A., Roberts A.L., and Fairbrother D.H. Anal. Chim. Acta 496 (2003) 301
35. Volpe A., Lopez A., Mascolo G., and Detomaso A. Chemosphere 57 (2004) 579
36. Quinn J., Geiger C., Clausen C., Brooks K., Coon C., O'Hara S., Krug T., Maior D., Yoon W.-S., Gavaskar A., and Holdsworth T. Environ. Sci. Technol. 39 (2005) 1309
37. Song H., and Carraway E. Environ. Sci. Technol. 39 (2005) 6237
38. Alonso F., and Yus M. Chem. Soc. Rev. 33 (2004) 284
39. Alonso F., Vitale C., Radivoy G., and Yus M. Synthesis (2003) 443
40. Radivoy G., Alonso F., Moglie Y., Vitale C., and Yus M. Tetrahedron 61 (2005) 3869
41. Moglie Y., Alonso F., Vitale C., Yus M., and Radivoy G. Tetrahedron 62 (2006) 2812
42. Alonso F., Radivoy G., and Yus M. Tetrahedron 55 (1999) 4441
43. Alonso F., Moglie Y., Radivoy G., Vitale C., and Yus M. Appl. Catal. A: Gen. 271 (2004) 171
44. Perrin D.D., and Amarego W.L.F. Purification of Laboratory Chemicals (1988), Pergamon Press, Oxford
45. Magai K. Bull. Chem. Soc. Jpn. 43 (1970) 2628
46. Wursthorn K.R., Kuivila H.G., and Smith G.F. J. Am. Chem. Soc. 100 (1978) 2779
47. Back T.G., Thomas G., Birss V.I., Edwards M., and Krishna M.V. J. Org. Chem. 53 (1988) 3815
48. 2-Li-DTBB(cat.) furnished unreacted starting material (63%), tetracosane (10%), dodecane (23%), and dodec-1-ene (4%). All the yields were determined by GLC/MS after 4 h using bromobenzene as an internal standard.
49. Kiplinger J.L., Richmond T.G., and Osterberg C.E. Chem. Rev. 94 (1994) 373
50. Burdeniuc J., Jedlicka B., and Crabtree R.H. Chem. Ber./Recl. 130 (1997) 145
51. Ogawa A. Organomet. News (2001) 17
52. Hoke J.B., Gramiccioni G.A., and Balko E.N. Appl. Catal. B: Environ. 1 (1992) 285
53. S. Kovenklioglu, E.N. Balko, J.B. Hoke, R.J. Farrauto, G.A. Gramiccioni, US Patent 5,196,617 (1993)
54. Kovenklioglu S., Balko E.N., Hoke J.B., Farrauto R.J., and Gramiccioni G.A. Chem. Abstr. 119 (1993) 79294
55. E.N. Balko, J.B. Hoke, G.A. Gramiccioni, US Patent 5,177,268 (1993)
56. Balko E.N., Hoke J.B., and Gramiccioni G.A. Chem. Abstr. 19 (1993) 188209
57. Marques C.A., Selva M., and Tundo P. J. Org. Chem. 58 (1993) 5256
58. Barren J.P., Baghel S.S., and McCloskey P.J. Synth. Commun. 23 (1993) 1601
59. Wei B., Li S., Lee H.K., and Hor T.S.A. J. Mol. Catal. A: Chem. 127 (1997) L83
60. Lassová L., Lee H.K., and Hor T.S.A. J. Org. Chem. 63 (1998) 3538
61. Yakovlev V.A., Simagina V.I., and Likholobov V.A. React. Kinet. Catal. Lett. 65 (1998) 177
62. Simagina V.I., Renouprez A.J., Bergeret G., Giménez M.T., Stoyanova I.V., Egorova M.B., and Likholobov V.A. Organohalogen Compd. 40 (1999) 563
63. Xu Y., and Zhang W. Ind. Eng. Chem. Res. 39 (2000) 2238
64. Simagina V.I., and Stoyanova I.V. Mendeleev Commun. (2001) 38
65. Verschueren K. Handbook of Environmental Data on Organic Chemicals. 4th ed. vol. 2 (1937), Wiley, New York pp. 1226, 1937
66. 2O after 4 h follow: (a) 4,4′-dibromobiphenyl gave 4-bromobiphenyl (37%) and biphenyl (63%); (b) 3,5-dichlorophenol gave the starting material (23%), 3-chlorophenol (21%), and phenol (56%); (c) p-chlorofluorobenzene gave the starting material (49%), fluorobenzene (18%), chlorobenzene (12%), and benzene (11%); (d) p-fluoroiodobenzene gave the starting material (37%), fluorobenzene (29%), iodobenzene (13%), and benzene (21%); (e) p-bromochlorobenzene gave the starting material (40%), chlorobenzene (22%), bromobenzene (15%), and benzene (23%). All the yields were determined by GLC/MS after 4 h using bromobenzene as an internal standard.