Homogeneous and Heterogeneous Hydrogenation of Nitriles in a Liquid Phase: Chemical, Mechanistic, and Catalytic Aspects

Catalysis Reviews - Science and Engineering - Tập 36 Số 3 - Trang 459-506 - 1994
Claude de Bellefon1, P. Fouilloux1
1Unité Mixte CNRS—Rhône Poulenc Rhône Poulenc Industrialisation 24 Avenue Jean Jaurès , 69153, Décines Charpieu, Cédex, France

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Kauffman G. B., 1988, J. Chem. Ed., 65, 803, 10.1021/ed065p803

Weissermel K., 1978, Industrielle Organische Chemie

Tolman C. A., 1986, J. Chem. Educ., 63, 199, 10.1021/ed063p199

Tinapp P., 1980, Methoden der Organische Chemie, p. 111

Volf, J. and Pasek, J. 1986.Stud. Surf. Sci. Catal., Edited by: Cerveny, L. Vol. 27, p. 105Amsterdam: Elsevier.

Peterson R. J., 1977, Chem. Technol. Rev., 94, 229

Montgomery, S. R. 1981.Catal. Org. React., Edited by: Moser, W. R. Vol. 5, p. 383New York: Dekker.

von Braun J., 1923, Chem. Ber., 36

Greenfield H., 1967, Ind. Eng. Chem. Prod. Res. Dev., 6, 142, 10.1021/i360022a014

Rylander, P. N. 1985.Hydrogenation Methods, p. 94London: Academic Press.

March J., 1985, Advanced Organic Chemistry

Tobias P. S., 1975, J. Am. Chem. Soc., 97, 6530, 10.1021/ja00855a041

Weng S., 1983, J. Am. Chem. Soc., 105, 4082, 10.1021/ja00350a056

Makela M. J., 1983, Chem. Soc. Rev., 12, 309, 10.1039/CS9831200309

Pietras S., 1955, Gazzetta, 85, 1705

Paez A., 1985, Rev. R. Acad. Cienc. Exactas, Fis. Nat. Madrid, 79, 197

Murahashi S.-I., 1992, J. Org. Chem., 57, 2521, 10.1021/jo00035a003

Djaouadi, D. 1993. Université de Grenoble 1. These de Doctorat

Krafft M. E., 1988, J. Org. Chem., 53, 3158, 10.1021/jo00249a007

Besson M., 1990, Bull. Soc. Chim. Fr., 127, 5

Kaniewska, E. J., Kowalczyk, A. M., Modzelewski, R. E. and Szelejewski, W. K. 1988.Stud. Surf. Sci. Catal., Edited by: Fine Chem, Hetero. Catal.Guisnet, M. Vol. 41, p. 387Amsterdam: Elsevier.

Baiker, A. 1988.Stud. Surf. Science Catal., Edited by: Fine Chem, Hetero. Catal.Guisnet, M. Vol. 41, p. 283Amsterdam: Elsevier.

Besson M., 1990, Bull. Soc. Chim. Fr., 127, 13

Turu, M. 1973. Université Catholique de Louvain-La-Neuve. Thèse de Doctorat

Dobrotvorskii A. M., 1987, Zhur. Prikl. Khim. (trans.), 60, 1087

Dallons, J. L., van Gysel, A. and Jannes, G. 1992.Catalysis of Organic Reactions, Edited by: Pascoe, W. E. p. 93New York: Dekker.

Pavlenko N. V., 1987, Kinet. Katal., 28, 1193

Freidlin Kh. L., 1964, Russ. Chem. Rev., 33, 319, 10.1070/RC1964v033n06ABEH001412

Marion, Ph., Joucla, M., Taisne, C. and Jenck, J. 1993.Stud. Surf. Sci. Catal., Edited by: Fine Chem, Hetero. Catal. IIIGuisnet, M. Vol. 78, p. 291Amsterdam: Elsevier.

Mares F., 1988, J. Catal., 112, 145, 10.1016/0021-9517(88)90128-5

Joucla, M., Marion, Ph., Grenouillet, P. and Jenck, J. 1994.Catalysis of Organic Reactions, Edited by: Kosak, J. R. and Johnson, T. A. p. 127New York: Dekker.

Ziemecki, S. B. 1993.Stud. Surf. Sci. Catal., Edited by: Fine Chem, Hetero. Catal. IIIGuisnet, M. Vol. 78, p. 283Amsterdam: Elsevier.

Dewdney, T. G., Dowden, D. A., Hawkins, B. D. and Morris, W. 1973. to Imperial Chemical Industries Ltd. FR 2243168

Bivens, D. B. and Patton, L. W. 1972. to E. I. du Pont de Nemours and Co. U.S. 3773834

Lazaris Ya. A., 1965, J. Appl. Chem. USSR, p. 1076

Andrade J. C., 1980, Synthesis, p. 802, 10.1055/s-1980-29210

Coons D. E., 1987, J. Am. Chem. Soc., 109, 283, 10.1021/ja00235a049

Thomas J. L., 1975, J. Am. Chem. Soc., 97, 5943, 10.1021/ja00853a066

Hemmer, R. and Lürken, W. 1992.Methoden der Organischen Chemie, Band E16d, Teil II, Edited by: Weyl, H. p. 1006Stuttgart: Georg Thieme Verlag.

Dallons J. L., 1985, Acta Chim. Hung., 119, 223

Barnett C., 1969, I. C. Prod. Res. Dev., 8, 145, 10.1021/i360030a009

Augustine, R. J. and O'Hagan, P. J. 1990.Catalysis of Organic Reactions, Edited by: Blackburn, D. W. p. 111New York: Dekker.

Gates B. C., 1993, Angew. Chem. Int. Ed. Engl., 32, 228, 10.1002/anie.199302281

Pombeiro A. J. L., 1990, Coord. Chem. Rev., 104, 13, 10.1016/0010-8545(90)80039-V

Bryan S. J., 1982, Coord. Chem. Rev., 44, 149, 10.1016/S0010-8545(00)80520-2

Storhoff B. N., 1977, Coord. Chem. Rev., 23, 1, 10.1016/S0010-8545(00)80329-X

Kilner M., 1972, Adv. Organomet. Chem., 10, 115, 10.1016/S0065-3055(08)60339-1

Bassi I. W., 1976, J. Organometal. Chem., 110, 129, 10.1016/S0022-328X(00)90166-9

Johnson B. F. G., 1982, J. Chem. Soc. Chem. Commun., p. 610, 10.1039/C39820000610

Dawson P. A., 1982, J. Chem. Soc. Dalton Trans., p. 233, 10.1039/dt9820000233

Johnson B. F. G., 1983, J. Chem. Soc. Dalton Trans., p. 277, 10.1039/DT9830000277

Barrera L., 1991, J. Am. Chem. Soc., 113, 8178, 10.1021/ja00021a060

Anderson S. J., 1988, Polyhedron, 7, 2615, 10.1016/S0277-5387(00)83883-8

Wright T. C., 1986, J. Chem. Soc. Dalton Trans., p. 2017, 10.1039/DT9860002017

Chetcuti P. A., 1988, Organometallics, 7, 650, 10.1021/om00093a013

Curran D. J., 1970, The Chemistry of the Carbon–Nitrogen Double Bond

Curran D. J., 1970, The Chemistry of the Cyano Group

Juchrovski I. N., 1983, Supplement C: The Chemistry of Triple Bonded Functional Groups

Cotton, F. A. and Wilkinson, G. 1985.Advanced Inorganic Chemistry, pp. 360–361. New York: Wiley. 5th ed.

Bland W. J., 1973, J. Chem. Soc. Dalton Trans., p. 1292, 10.1039/DT9730001292

Feng Q., 1991, J. Chem. Soc. Chem. Commun., p. 552, 10.1039/C39910000552

Barron A. R., 1987, J. Chem. Soc. Dalton Trans., p. 2947, 10.1039/DT9870002947

McGilligan B. S., 1988, J. Chem. Soc. Dalton Trans., p. 1737, 10.1039/DT9880001737

He Z., 1992, Organometallics, 11, 817, 10.1021/om00038a047

Andrews M. A., 1977, J. Am. Chem. Soc., 99, 6763, 10.1021/ja00462a053

Andrews M. A., 1979, J. Am. Chem. Soc., 101, 7238, 10.1021/ja00518a018

Andrews M. A., 1979, J. Am. Chem. Soc., 101, 7255, 10.1021/ja00518a020

Andrews M. A., 1979, J. Am. Chem. Soc., 101, 7245, 10.1021/ja00518a019

Andrews M. A., 1979, J. Am. Chem. Soc., 101, 7260, 10.1021/ja00518a021

Lausarot P. M., 1984, J. Organometal. Chem., 273, 239, 10.1016/0022-328X(84)80528-8

Bernhardt W., 1984, Angew. Chem. Int. Ed. Engl., 23, 381, 10.1002/anie.198403811

Bernhardt W., 1988, Z. Naturforsch., 43, 643, 10.1515/znb-1988-0601

Lausarot P. M., 1985, J. Organometal. Chem., 291, 221, 10.1016/0022-328X(85)80171-6

Dawoodi Z., 1981, J. Organometal. Chem., 219, 103, 10.1016/0022-328X(81)85014-0

Adams R. D., 1981, J. Organometal. Chem., 219, 85, 10.1016/0022-328X(81)85013-9

Garcia Alonso F. J., 1992, Organometallics, 11, 801, 10.1021/om00038a045

Prest D. W., 1982, J. Chem. Soc. Dalton Trans., p. 2021, 10.1039/DT9820002021

Mays M. J., 1980, J. Chem. Soc. Chem. Commun., p. 171, 10.1039/C39800000171

Evans W. J., 1984, J. Am. Chem. Soc., 106, 1291, 10.1021/ja00317a020

Erker G., 1984, Angew. Chem. Int. Ed. Engl., 23, 68, 10.1002/anie.198400681

Frömberg W., 1985, J. Organometal. Chem., 280, 343, 10.1016/0022-328X(85)88111-0

Kreutzer K. A., 1991, Organometallics, 10, 4031, 10.1021/om00058a018

Banford J., 1982, J. Chem. Soc. Chem. Commun., p. 554, 10.1039/C39820000554

Adams, R. D. 1990.Metal–Metal Bonds and Clusters in Chemistry and Catalysis, Edited by: Fackler, J. P. Jr. pp. 75–89. New York: Plenum Press.

Gabor B., 1991, Angew. Chem. Int. Ed. Engl., 30, 1666, 10.1002/anie.199116661

Feng S. G., 1989, J. Am. Chem. Soc., 111, 6477, 10.1021/ja00198a099

Anderson S. J., 1987, Polyhedron, 6, 1089, 10.1016/S0277-5387(00)80914-6

Paul P., 1987, Inorg. Chem., 26, 1586, 10.1021/ic00257a024

Wada M., 1976, Inorg. Chem., 15, 954, 10.1021/ic50158a045

Syamala A., 1991, Inorg. Chem., 30, 4699, 10.1021/ic00025a006

Bercaw J. E., 1986, Organometallics, 5, 443, 10.1021/om00134a009

Robinson V., 1981, J. Chem. Soc. Dalton Trans., p. 1169, 10.1039/DT9810001169

Heldt W. Z., 1966, J. Organometal. Chem., 6, 292, 10.1016/S0022-328X(00)88742-2

Yang D. C., 1988, J. Am. Chem. Soc., 110, 307, 10.1021/ja00209a059

Schenkluhn, H. 1971. “Dissertation”. Böchum: Ruhr Universität.

Doxsee K. M., 1990, Organometallics, 9, 3012, 10.1021/om00162a004

Jordan R. F., 1990, New J. Chem., 14, 505

Wood C. D., 1979, J. Am. Chem. Soc., 101, 3210, 10.1021/ja00506a014

Rehbaum F., 1991, J. Organometal. Chem., 410, 327, 10.1016/0022-328X(91)83006-P

Duchateau R., 1991, Inorg. Chem., 30, 4863, 10.1021/ic00025a036

DeBoer E. J. M., 1977, J. Organometal. Chem., 140, 41, 10.1016/S0022-328X(00)84394-6

DeBoer E. J. M., 1978, J. Organometal. Chem., 153, 53, 10.1016/S0022-328X(00)90931-8

Roskamp E. J., 1987, J. Am. Chem. Soc., 109, 3152, 10.1021/ja00244a052

Finn P. A., 1975, J. Am. Chem. Soc., 97, 220, 10.1021/ja00834a056

Cotton F. A., 1978, Inorg. Chem., 17, 3525, 10.1021/ic50190a039

1979, J. Am. Chem. Soc., 101, 5094, 10.1021/ja00511a064

Schögl R., 1993, Angew. Chem. Int. Ed. Engl., 32, 381, 10.1002/anie.199303811

Hager, G. F. 1950. to E. I. Du Pont de Nemours and Co. U.S. 2644842

Joshi, A. M., MacFarlane, K. S., James, B. R. and Frediani, P. 1992.Progress in Catalysis, Edited by: Smith, K. J. and Sanford, E. C. p. 143New York: Elsevier.

Holy N. L., 1979, J. Org. Chem., 44, 239, 10.1021/jo01316a018

Holy N. L., 1978, J. Chem. Soc. Chem. Commun., p. 1074, 10.1039/c39780001074

Bayer E., 1986, J. Chem. Soc. Chem. Commun., p. 949, 10.1039/c39860000949

Parshall, G. W. 1970. to E. I. Du Pont de Nemours and Co. U.S. 3657368

Sabatier P., 1905, Comptes Rendus Acad. Sci., Paris, 140, 482

Battino R., 1981, The Solubility of Gases in Liquids, IUPAC Data Series

Brunner R., 1978, Ber. Bunsenges. Phys. Chem., 82, 798, 10.1002/bbpc.19780820807

Hartung W. H., 1928, J. Am. Chem. Soc., 50, 3370, 10.1021/ja01399a033

Carothers W. H., 1925, J. Am. Chem. Soc., 47, 3051, 10.1021/ja01689a034

Gould F. E., 1960, J. Org. Chem., 25, 1658, 10.1021/jo01079a600

Takagi Y., 1967, Sci. Pap. Inst. Phys. Chem. Res. Tokyo, 61, 114

Paul R., 1946, Bull. Soc. Soc. Chim. France, p. 208

Paul R., 1952, Ind. Eng. Chem., 44, 1006, 10.1021/ie50509a029

Rylander P. N., 1970, Engelhard Ind. Techn. Bull., 11, 19

James B. R., 1973, Homogeneous Hydrogenation

Fell B., 1991, Chem. Zeit., 115, 83

Fell B., 1991, Fat. Sci. Technol., 93, 79

Kroll, W. R. 1968. to Esso Res. and Eng. Co. U.S. 3412174

1969, J. Catal., 15, 281, 10.1016/0021-9517(69)90290-5

Waddan, D. and Williams, D. F. 1969–1968. to Imperial Chemical Industries Ltd. DE 1904613

Durand, D., Hillion, G., Lassau, C. and Sajus, L. 1973. to Institut Français du Pétrole. FR 2249709

Bönnemann H., 1991, Angew. Chem. Int. Ed. Engl., 30, 1312, 10.1002/anie.199113121

Schmid G., 1992, Chem. Rev., 92, 1709, 10.1021/cr00016a002

Morris, W., Waddan, D. and Williams, D. F. 1969. to Imperial Chemical Industries Ltd. DE 2052730

Blanchard, M., Barrault, J. and Derouault, A. 1991.Stud. Surf. Sci. Catal., Edited by: Catalysts, V., Poncelet, G., Jacobs, P. A., Grange, P. and Delmon, B. p. 687Amsterdam: Elsevier. Preparation of

Oden, L. L., Sanker, P. E. and Russel, J. H. 1976. Vol. No. 8184, U.S. Bureau of Mines. Report of Investigation

Lemkey F. D., 1965, Trans. AIME, 233, 334

Fasman A. B., 1976, Zh. Fiz. Khim., 50, 1720

Bonnier J. M., 1987, J. Chim. Phys. Chim. Biol., 84, 889, 10.1051/jcp/1987840889

Colin-Urtado, P. 1990. Thèse de l'Institut National Polythechnique de Grenoble.

Nalibaev T. N., 1974, Russ. J. Phys. Chem., 48, 511

Gros J., 1989, J. Mater. Sci., 24, 2987, 10.1007/BF02385658

Timofeeva V. F., 1978, Russ. J. Phys. Chem., 52, 966

Maksimova N. A., 1988, Izv. Akad. Nauk Kaz. SSR, Ser. Khim., 2, 29

Brooks C. S., 1982, Surf. Technol., 16, 67, 10.1016/0376-4583(82)90096-6

Brooks, C. S., Lemkey, F. D. and Golden, G. S. 1982.Rapidly Solidified Amorphous and Crystalline Alloys, Edited by: Kear, B. H., Giessen, B. C. and Cohen, M. pp. 397–407. Elsevier.

Brooks, C. S., Lemkey, F. D. and Golden, G. S. 1976. to United Technologies. U.S. 4096284

Brooks, C. S., Lemkey, F. D. and Golden, G. S. 1979.Proc. 3rd Conf. on In Situ Composites, p. 221MA: Ginn Custom.

Fouilloux P., 1972, J. Catal., 25, 212, 10.1016/0021-9517(72)90220-5

Freel J., 1969, J. Catal., 14, 247, 10.1016/0021-9517(69)90432-1

Martin G. A., 1975, J. Catal., 38, 231, 10.1016/0021-9517(75)90083-4

Vishnevetskii E. A., 1986, React. Kinet. Catal. Lett., 31, 445, 10.1007/BF02072986

Kurata H., 1985, Bull. Inst. Chem. Res., Kyoto Univ., 63, 216

Spindler, J. F., Jenck, J. and Fouilloux, P. 1993.Proc. 10th Int. Cong. on Catalysis, p. 2555Akademiai Kiado Budapest.

Delannay F., 1982, Appl. Catal., 4, 169, 10.1016/0166-9834(82)80248-0

Vishnevetskii E. A., 1986, React. Kinet. Catal. Lett., 31, 445, 10.1007/BF02072986

Kenjo T., 1988, Electrochim. Acta, 33, 41, 10.1016/0013-4686(88)80029-X

Moroz E. M., 1991, React. Kinet. Catal. Lett., 43, 63, 10.1007/BF02075413

Fouilloux P., 1983, Appl. Catal., 8, 988, 10.1016/0166-9834(83)80051-7

Stockmeyer R., 1975, Surf. Sci., 49, 549, 10.1016/0039-6028(75)90370-2

Renouprez A. J., 1977, J. Chem. Soc. Faraday Trans. 1, 72, 1, 10.1039/f19777300001

MacNab J., 1973, J. Catal., 29, 338, 10.1016/0021-9517(73)90238-8

Mathieu C., 1992, Chem. Eng. Sci., 47, 2289, 10.1016/0009-2509(92)87049-V

Polkovnikov V. D., 1959, Izv. Akad. Nauk SSSR, Otdel Khim. Nauk, p. 1488

Keller E., 1984, Chem. Ber., 117, 1572, 10.1002/cber.19841170425

Walther D., 1987, J. Organometal. Chem., 334, 377, 10.1016/0022-328X(87)80100-6

Bassi I. W., 1978, J. Organometal. Chem., 144, 225, 10.1016/S0022-328X(00)84165-0

Gardin D. E., 1992, J. Phys. Chem., 96, 9424, 10.1021/j100202a067

Friend C. M., 1981, J. Phys. Chem., 85, 3256, 10.1021/j150622a011

Sexton B. A., 1983, Surf. Sci., 129, 21, 10.1016/0039-6028(83)90092-4

Levering, D. R. 1962. to Hercules Powder Co. U.S. 3152184

Ucciani E., 1982, Rev. Franç. Corps Gras, 29, 219

Muetterties E. L., 1980, Inorg. Chem., 19, 1552, 10.1021/ic50208a024

Levering, D. R. 1960. to Hercules Powder Co. U.S. 3065250

Dewhirst, K. C. 1966. to Shell Oil Co. U.S. 3454644

Grey R. A., 1981, J. Am. Chem. Soc., 103, 7536, 10.1021/ja00415a022

James B. R., 1987, J. Mol. Cat., 41, 147, 10.1016/0304-5102(87)80025-1

Thorburn I. S., 1985, J. Organomet. Chem., 296, 103, 10.1016/0022-328X(85)80342-9

Suarez T., 1988, J. Mol. Catal., 45, 335, 10.1016/0304-5102(88)80065-8

Pez G. P., 1984, Fund. Res. Homog. Catal., 4, 97

1980, Prepr. Pap. Natl. Meet. Div. Petrol., Am. Chem. Soc., 25, 399

Grey, R. A. and Pez, G. P. 1979. to Allied Chem. Corp. U.S. 4254059

Yoshida T., 1979, J. Chem. Soc. Chem. Commun., p. 870, 10.1039/C39790000870

Diamond, S. E., Mares, F. and Szalkiewicz, A. 1981. to Allied Corp. U.S. 4362671

Mukherjee D. K., 1992, Ind. J. Chem., 31, 243

Bose A., 1989, J. Mol. Catal., 49, 271, 10.1016/0304-5102(89)85017-5

Chin C. S., 1992, Catal. Lett., 14, 135, 10.1007/BF00764228

Bhaduri S., 1982, J. Chem. Soc. Dalton Trans., p. 727, 10.1039/dt9820000727

Pertici P., 1981, J. Mol. Catal., 11, 353, 10.1016/0304-5102(81)87023-X

Ciardelli F., 1985, Z. Naturforsch., 40, 133, 10.1515/znb-1985-0201

Dines, M. B., DiGiacomo, P. M. and Callahan, K. P. 1981. to Occidental Research Corp. U.S. 4384981

Durand, D., Hillion, G., Lassau, C. and Sajus, L. 1973. to Institut Français du Pétrole. FR 2228536

Badische Anilin, 1952, Ger., 848, 654

Reck, R. A. 1990.Surfactant Science Series, Vol. 34, Cationic Surfactant Organic Chemistry, p. 163New York: Dekker.

Rylander, P. N. 1967.Catalytic Hydrogenation over Platinum Metals, p. 203New York: Academic Press.

Freifelder, M. 1971.Practical Catalytic Hydrogenation, p. 346New York: Willey.

Galan A., 1991, J. Org. Chem., 56, 452, 10.1021/jo00001a088

Barrault, J., Brunet, S., Essayem, N., Piccirilli, A. and Guimon, C. 1993.Stud. Surf. Sci. Catal., Edited by: Fine Chem., Hetero. Catal. IIIGuisnet, M. Vol. 78, p. 305Amsterdam: Elsevier.

Baiker, A. 1988.Stud. Surf. Sci. Catal., Edited by: Fine Chem., Hetero. Catal. IGuisnet, M. Vol. 41, p. 283Amsterdam: Elsevier.

Malz, R. E. and Greenfield, H. 1991.Stud. Surf. Sci. Catal., Edited by: Fine Chem., Hetero. Catal. IIGuisnet, M. Vol. 59, p. 351Amsterdam: Elsevier.