Abstract
Recent results on hyd rode halogenation (HDH) of alkyl halides, freons, aryl halides, polychlorinated derivatives of benzodioxines and biphenyls, and other compounds in the presence of heterogeneous and homogeneous catalysts are generalized, Effective and selective hydrodehalogenation proceedsvia anion or radical anion intermediates. Special attention is given to the nature of the source of the hydrogen replacing the halogen.
Similar content being viewed by others
References
A. R. Pinder, Synthesis, 1980, 425.
I. A. Cusumano,in TOCAT 2. (Second Tokyo Canf. on Advanced Catalytic Science and Technology), Aug. 21–26 (1994), Progr.-Abstr., 403.
J. R. Shoebrecht and F. Janssens, Eur. Pat, 570,050.Chem., Abstr., 1994,120, 106376.
T. Suzuki and S Kawahara, JP 04,364,136,Chem. Abstr., 1992,118, 254378,
E. I. Gelperin, Yu. M. Bakshi, J. V. Tarasova, A. K. Avetisov, R. Touride, O. Finlayson, and M. Tierman,Proc II Conf. “Martern Trends in Chemical Kinetics and Catalysis,” Part H(1). November 21–24, 1995, Novosïbirsk, Russia, 218.
S. Marikawa, S. Samejima, M. Yashitake, S. Tatematsu, JP 04-264,136,Chem. Abstr., 1990,116, 255162.
G. S. Dasaeva, S. M. Velichko, Yu. A. Treger, and I. I. Moiseev,Kinet. Katal., 1990,31, 858 [Kinet. Catal., 1990,31 (Engl. Transl.)].
L. J. Matheson and P. G. Tratnyek,Environ. Sci. Technol., 1994,28, 2045.
O. A. Zaidman, E. L Verkhatova, L. N. Zanaveskin, and Yu. A. Treger,Khim. Prom-st [Chemical Indsutry], 1991, 515 (in Russian).
C D. Schreier and M. Reinhard,Chemosphere, 1995,31, 3475.
E. D. Boyes, D. R. Coulson, G. W. Coulston, M. P. Diebold, P. L. Gai, G. A. Jones, C. S. Kellner, J. J. Leron, and L. E. Manzer,Prepr.-Am. Chem. Soc., Div. Pet. Chem., 1993,38 (4), 847,Chem. Abstr., 1994,120, 220759.
I. Pri-Bar, D. Azoulay, and O. Buchman, Eur. Pat. 456, 879,Chem. Abstr., 1990,116, 1122944.
S. Marikawa, S. Sameijima, M. Yositake, and S. Tatematsu, J P 04-29941,Chem. Abstr., 1990,116, 255164.
N. Takada, T. Moruta, and H. Ooshio, 1P 04-13638,Chem. Abstr., 1990,116, 193698.
W. Dafinger and L. Schmidhammer, Eur. Pat. 523,553,Chem. Abstr., 1993,118, 236 404.
R. Ohnishi, W. L. Wang, and M. Ishikawa,Appl. Catal. A, 1994,113, 29.
R. M. Jansen, Eur. Pat.571,420,Chem. Abstr., 1994,120, 133827.
C. J. Shields and G. Goodyear, PCT Int. Appl. WO 44 02439,Chem. Abstr., 1994,120, 191 107.
H. Aoyama, E. Seki, and S. Koyama, PCT Int. Appl. WO 93 16023,Chem. Abstr., 1994,120, 54176.
S. Marikawa, M. Yashitake, and S. Tatematsu, JP 05-17379,Chem. Abstr.,1992,118, 254379.
R. Ohnishi, H. Suzuki, W. Wang, and M. Ishikawa,Sekubai (Catalyst), 1991,33, 91.
J. Takita, H. Yamada, Y. Mizuhara, and T.Ishihara,Chem. Express, 1990,5, 785.
Y. Takita, H. Yamada, T. Ishilrara, and Y. Mizuhara,J. Chem. Soc. Japan, Chem. Ind. Chem., 1991,5, 584.
T. Mori, W. Ueda, and Y. Marikawa,TOCAT 2 (Second Tokyo Conf on Advanced Catalytic Science and Technology) Aug. 21–26 (1994), Progr.—Abstr., 403.
N. N. Kuznetsova, E. S. Lakteva, V. V. Lunin, and S. L. Yudina,Kinet. Katal., 1995,36, 13l [Kinet. Catal., 1995,36 (Engl. Transl.)].
J. M. Cognion and D. Guillet, Eur. Pat. 506525,Chem. Abstr., 1991,117, 233429.
J. Koppe, K. Kraenke, D. Shoenfeld, and H. Haugk, Ger. Pat. DE 4200790,Chem. Abstr., 1994,120, 61641.
F. Zaera and S. Tjandra,J. Phys. Chem., 1994,48, 3044.
K. Ogura, J. Guo, and Y. Jun,Huanjing Huauue, 1993,12, 66,Chem. Abstr., 1993,119, 54985.
S. Okazaki and H. Habutsu,J. Fluorine Chem., 1992,57, 191.
Y. Morikawa, T. Ikawa, and W. Ueda, 1P 04-120032,Chem. Abstr., 1991,117, 111129.
Y. Marikawa, T. Ikawa, W. Ueda, JP 04-120031,Chem Abstr. 1991,117, 111128.
A. Stüre, J. Grub, and M. Lux, Pat. BRD 40120074, 1490
J. Mochida, Y.Kojima, H. Tejima, and M. Morita, 1P 05-271123,Chem, Abstr., 1994,120, 133826.
T. Yoshida, T. Honda, and K. Nakagawa, 1P 03-264542,Chem. Abstr.,1990,116,173551.
R. B. Timmons, W. L. Jang, Y. He, and D. J. Haupt, US Pat. 5,276,240,Chem. Abstr., 1994,120, 216696.
E. S. Lakteva, V. V. Lenin, A. N. Kovredov, and L. I. Zakharkin,Izv. Akad. Nauk SSSR, Ser. Khim., 1984, 539 [Bull. Acad. Sci., 1989,38, 473 (Engl. Transl.)].
C. B. Castro, M. C. Helvenston, and N. O. Belser,Environ. Toxicol. Chem., 1994,13, 249.
T. Arai, K. Kashitani, H. Kando, and S. Sasaki,Bull. Chem. Soc. Japan, 1994,67, 705.
C. J. Gantzer and L. R. Wackett,Environ Sci. Technol., 1991,25, 715.
V. V. Lunin and E. S. Lokteva,Kinet. Katal., 1989,30, 674 [Kinet. Catal., 1989,30 (Engl. Transl)].
R. G. Harrison and T. G. Richmond,J. Am. Chem. Soc., 1993,115, 5303.
S. Li and L. R. Wackett,Biochemistry, 1993,32, 9355.
U. E. Krone, R. K. Thauer, and H. R. C. Hagenkamp,Biochemistry, 1989,28, 4908.
R. J. Kuhler, G. Santo, T. R. Candill, E. A. Betterton, and R. G. Arnold,Environ. Sci. Technol., 1993,27, 2104.
V. V. Yanilkin, N. I. Maksimyuk, and Yu. M. Kargin,Izv. Akad. Nauk, Ser. Khim., 1994, 1022 [Russ. Chem. Bull.,43, 957 (Engl. Transl.)]
V. V. Yanilkin, N. L Maksimyuk, E. L Gritsenko, and Yu. M. Kargin,Izv. Akad. Nauk, Ser. Khim., 1991, 261 [Russ. Chem. Buil., 1991,40, 241 (Engl. Transl.)]
A. G. Anshits, A. R. Suzdorf, S. I. Tsiganova, and N. N. Anshits,EuroCat-1 (1st Eur. Cangr. Catal., Montpellier. Sept.12-17 1993), Book Abstr.,2, 1993, 926.
A. R. Suzdorf, S. I. Tsyganova, N. N. Anshits, S. V. Morozov, anti A. G. Anshits,Sib. Khim. Zh. [Siberian Chem. J.], 1992, No. 6, l31 (in Russian.
E. J. Greyghton, M. N. W. Burgers, J. C. Japsen, and H. van Bekkum,Appl. Catal., A: Gen., 1945,128, 275.
V. I. Simagina, I. V. Stajanova, V. M. Mastikhin, E. M. Moroz, V. A. Yakovlev, and V. A. Likholobov,Proc. 11 Conference “Modern Trends in Chemical Kinetics and Catalysis,” Part I(2), November 21–24, 1995, Novosibirsk, Russia, 361.
V. N. Isaeva, Ya. V. Smirnova, and V. Z. Sharf,Izv. Akad. Nauk, Ser. Khim., 1993, 613 [Russ. Chem. Bull., 1993,42, 582 (Engl. Transl.)]
V. Z. Sharf, L. Kh. Freidlin, and V. N. Krutii,Izv. Akad. Nauk SSSR, Ser. Khim., 1977, 735 [Bull. Acad. Sci. USSR, Div. Chem. Sci.,26 (Engl. Transl.)]
V. Z. Sharf, L. Kh. Freidlin, L S. Shekoyan, V. N. Krutii,Izv. Akad, Nauk SSSR, Ser. Khim., 1977, 834 [Bull. Acad. Sci., Div. Chem. Sci., 1977,26, no. 4 (Engl. Transl.)]
T. Schach and T. Papenfuhs, Eur. Pat. 598,338,Chem. Abstr., 1995,121, 108188.
V. Z. Sharf and V. I. Isaeva,Stud. Surf Sci, Catal., 1993,75, 2281.
W. Fahruschen, P. Kripylo, J. Koppe, and M. Wilde, Ger. Offen, DE. 4-230553,Chem. Abstr., 1995,121, 159725.
H. Yamanaka, R. Oshima, K. Teramura, and T. Ando.J. Org. Chem., 1972,37, 1734.
K. Isogai and T. Kazama,Nippon Kagaku Zassi. J. Chem Soc. Japan, 1967,88, 106.
E. S. Lokteva, T. E. Klimova, V. V. Lupin,Vestn. Mosk. Un-ta, Ser. 2, Khim. [Bull. Moscow Univ., Ser. 2, Chenr.], 1986,27, S87 (in Russian).
M. Sakai, M. Lee, K. Yamaguchi, Y. Kawai, K. Sasaki, and Y. Sakakibara,Bull. Chem. Soc. Japan, 1992,65, 1739.
V. I. Krasnov and V. E. Platonav,Zh. Org. Khim., 1993,24, 107 [J. Org. Chem., 1993,29 (Engt. Transl.)].
M. Farfcasiu, S. C. Petrasius, and E. P. Ladner,J. Catal., 1994,146, 313.
M. Moeder, D. Bender, and G. Reinhardt, Ger. (East) DD 294965,Chem. Abstr., 1990,116, 151297.
F. Gicla, V. Famiglietti, and F. Murera,J. Hazard. Mater., 1993,33, 63.
F. Giola, V. Famiglietti, and F. Murera,J. Hazard. Mater., 1994,38, 277.
M. Novak and M. Zdrazil,Bull. Svr. Chim. Belg., 1993,102, 271.
Y. Ben-David, M. Gozin, M. Partnoy, and D. Milshtein,J. Mol. Catal., 1992,73, 173.
R. F. Heck,Palladium Reagents in Organic Synthesis, Academic Press, London, 1985, 461.
H. Imai, T. Nishiguchi, M. Tanaka, and K. Fucuzumi,J. Org. Chem., 1977,42, 2309.
Y. Sasson and J. Blum,J. Org. Chem., 1975,40, 1887.
S. M. H. Tabaei and C. U. I. Pittman,Hazard. Waste Hazard. Mater., 1993,10, 431.
M. Stiles,J. Org. Chem., 1994,59, 5381.
D. T. Fernrghelh anti J. T. Horvath,J. Chem. Soc. Chem Communs., 1992, 806.
M. H. Smïth,From Diss. Abstr. lnt. B, 1994,54 (9), 4586,Chem. Abstr., 1994,120, 265678.
G. A. Tolstikov and S. S. Savanov,Proc. 11 Conference “Modern Trends in Chemical Kinetics and Catalysis,” Part 1, November 21–24, 1995, Navasibirsk, Russia, 44.
C. A. Margues, M. Selva, and P. Tunda,J. Org. Chem., 1993,58, 5256.
C. A. Marques, M. Selva, and P. Tunda,J. Org. Chem., 1994,54, 3830.
C. A. Margues, M. Selva, and P. Tunda,J. Chem. Soc Perkin Trans., I., 1993, 529.
I. Pri-Bar and O. Buchman,J. Org. Chem., 1986,51, 734.
V. V. Grushin and H Alper,Organometallics, 1991, 1620.
S. M. H. Tabaei, C. U. I. Pittman, and K. T. Mead,J. Org. Chem., 1992,57, 6669.
J. A. Roth, S. R. Dakoji, R. E. R. C. Hughes, and R. E. Carmody,Environ. Ser. Technol., 1994,28, 80.
G. A. Elping, E. M. Florio, A. J. Baurque, X.-H. Quan, and J. D. Stuart,Envron. Sci. Technol., 1988,22, 952.
S. Zhang and J. Rusting,Environ. Sci. Technol., 1993,27, 1375.
V. A. Simagina,L V. Stojanova, V. V.Litvak, V.M. Mastikhin, V, A. Jakovlev, and V. A. Likholabov, inEUROPACAT-II (II Eur. Cangr. Catal., Maastricht, Sept. 3–8, 1993), Book of Abstracts, 329.
Y. Liu, J. Schwartz, and C. L. Cavallaro,Environ. Sci. Technol., 1993,27, 1375.
F.-W. Chuang, R. A. Larson, and M. S. Wessman,Environ. Sci. Technol., 1995,24, 2460.
C. Grittini, M. Malkamson, Q. Fernando, and N. Corte,Environ. Sci. Technol., 1995,24, 2898.
V. Z. Sharf, V. F. Davganyuk, V. L Isaeva, and B. I. Maksimov,Izv. Akad. Nauk SSSR, Ser. Khim., 1989, 534 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1989,38, 468 (Engl. Transl.)]
B. J. Cote, D. Despres, R. Labrecque, J. Lamothe, J. M. Chapuzet, and I. Lessard,J. Electroanal. Chem., 1993,355, 219.
R. G. Compton, R. A. W. Dryfe, and A. C. Fisher.J. Electroanal. Chem., 1993,361, 275.
A. R. Suzdorf, S. V. Morozov, A. M. Covalev, and A. G. Anshits, in:EUROP.ICAT-II, (2 Eur. Cangr. Catal., Maastricht, Sept. 3–8 1993) Book of Abstracts, 337.
K. Hirata and H. Kaai, JP 05-339236,Chem. Abstr., 1994,120, 244702.
M. V. Klyuev, A. A. Nazivilin, and N. V. Sidorova,Author`s Certificate 1643535 USSR,Byul. Izobre. [Bull. Invent.], 1991, 1986 (in Russian).
R. G. Pews, J. E. Hunter, and R. M. Wehmeyer,Tetrahedron, 1993,49, 4809.
D. V. Davydov and I. P. Beletskaya,Metalloorg. Khim., 1993,3, 111 [Organomet. Chenr. USSR, 1993,3 (Engl. Transl.)].
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1609–1624, July. 1996.
Rights and permissions
About this article
Cite this article
Lunin, V.V., Lokteva, E.S. Catalytic hydrodehalogenation of organic compounds. Russ Chem Bull 45, 1519–1534 (1996). https://doi.org/10.1007/BF01431781
Issue Date:
DOI: https://doi.org/10.1007/BF01431781