Iridium(0) nanocluster, acid-assisted catalysis of neat acetone hydrogenation at room temperature: Exceptional activity, catalyst lifetime, and selectivity at complete conversion

Journal of the American Chemical Society

Volumn 127, Issue 13, 2005, Pages 4800-4808

  Özkart, Saim ^a   Finke, Richard G ^b  

^a MIDDLE EAST TECHNICAL UNIVERSITY   (Turkey)

^b Immunology and Pathology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; FUEL CELLS; HYDROGENATION; IRIDIUM COMPOUNDS; MOLECULAR SIEVES; NANOSTRUCTURED MATERIALS; PRECIPITATION (CHEMICAL); PRESSURE EFFECTS;

ACETONE HYDROGENATION CATALYSIS; CATALYST SYSTEMS; HEAT PUMPS; IRIDIUM(0) NANOCLUSTERS;

CATALYSIS;

2 PROPANOL; ACETONE; HYDROCHLORIC ACID; IRIDIUM;

ARTICLE; CATALYSIS; ENZYME ACTIVITY; ENZYME KINETICS; ENZYME MECHANISM; HYDROGENATION; LOW TEMPERATURE PROCEDURES; PRECIPITATION; PRESSURE; REACTION ANALYSIS; ROOM TEMPERATURE; TEMPERATURE DEPENDENCE;

EID: 16844371004     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0437813     Document Type: Article

References (146)

1. Anderson, L. C.; MacNaughton, N. W. J. Am. Chem. Soc. 1942, 64, 1456.
2. Methyl isobutyl ketone is used as a solvent for vinyl, epoxy, and acrylic resins as well as cellulose-based coatings, (a) Gandia, L. M.; Montes, M. Appl. Catal., A: General 1993, 101, L1.
3. (b) Reith, W.; Dettmer, M.; Widdecke, H.; Fleischer, B. Stud. Surf. Sci. Catal. 1991, 59, 487.
4. Note that the preferred operating temperature in the heat-pump application is around 200 °C: (a) Wojcik, A. M. W.; van der Koi, H. J.; Maschmeyer, T. J. Phys. D: Appl. Phys. 2001, 34, 660-666.
5. (b) Gandia, L. M.; Montes, M. Int. J. Energy Res. 1992, 16, 851-864.
6. (c) Meng, N.; Shinoda, S.; Saito, Y. Int. J. Hydrogen Energy 1997, 22, 361-367.
7. (d) Chung, Y.; Kim, B. J.; Yeo, Y. K.; Song, H. K. Energy 1997, 22, 525-536.
8. (a) Ando, Y.; Tanaka, T.; Doi, T.; Takashima, T. Energy Convers. Manage. 2001, 42, 1807-1816.
9. (b) Pardillos-Guindet, J.; Metais, S.; Vidal, S.; Court, J.; Foulloux, P. Appl. Catal., A 1995, 132, 61-75.
10. (c) Pardillos-Guindet, J.; Vidai, S.; Court, J.; Foulloux, P. J. Catal. 1995, 155, 12-20.
11. Reviews: (a) Birch, A. J.; Williamson, D. H. Org. React. (N. Y.) 1976, 24, 1-186.
12. (b) Matteoli, U.; Frediani, P.; Binachi, M.; Botteghi, C.; Gladiali, S. J. Mol. Catal. 1981, 12, 265-319.
13. (c) Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051-1069.
14. (d) de Graauw, C. F.; Peters, J. A.; van Bekkum, H.; Huskens, J. Synthesis 1994, 1007-1017.
15. (e) Gladiali, S.; Mestroni, G. Transition Met. Org. Synth. 1998, 2, 97-119.
16. (f) Palmer, M. J.; Wills, M. Tetrahedron: Asymmetry 1999, 10, 2045-2061.
17. (g) Wills, M.; Palmer, M.; Smith, A.; Kenny, J.; Walsgrove, T. Molecules 2000, 5, 4-18.
18. (h) Wills, M.; Gamble, M.; Palmer, M.; Smith, A.; Studley, J.; Kenny, J. J. Mol. Catal. A 1999, 146, 139-148.
19. (i) Fache, F.; Schulz, E.; Tommasino, M. L.; Lemaire, M. Chem. Rev. 2000, 100, 2159-2231.
20. (j) Casey, C. P.; Johnson, J. B. J. Org. Chem. 2003, 68, 1998.
21. (a) Wilds, A. L. Org. React. (N. Y.) 1944, 2, 178-223.
22. (b) Djerassi, C. Org. React. (N. Y.) 1951, 6, 207-272.
23. (c) Namy, J. L.; Souppe, J.; Collin, J.; Kagan, H. B. J. Org. Chem. 1984, 49, 2045-2049.
24. (d) Hallman, P. S.; McGarvey, B. R.; Wilkinson, G. J. Chem. Soc. A 1968, 3143-3150.
25. Raney nickel as catalyst: (a) Freund, T.; Hulburt, H. M. J. Phys. Chem. 1957, 61, 909.
26. (b) Kishida, S.; Teranishi, S. J. Catal 1968, 12, 90.
27. (c) Lemcoff, N. O. J. Catal. 1977, 46, 356-364.
28. Silica-supported Co, Ni, Cu, Rh, Pd, Pt, and Au catalysts: (a) Van Druten, G. M. R.; Ponec, V. React. Kinet. Catal. Lett. 1999, 68, 15-23.
29. (b) Van Druten, G. M. R.; Aksu, L.; Ponec, V. Appl. Catal., A 1997, 149, 181-187.
30. (c) Gandia, L. M.; Diaz, A.; Montes, M. J. Catal. 1995, 157, 461-471.
31. (d) Nakamura, M.; Wise, H. In Proceedings of the 6th International Congress on Catalysis, London, 1976; Bond, G. C., Wells, P. B., Tompkins, F. C., Eds.; The Chemical Society: London, 1977; p 881.
32. (d) Nakamura, M.; Wise, H. In Proceedings of the 6th International Congress on Catalysis, London, 1976; Bond, G. C., Wells, P. B., Tompkins, F. C., Eds.; The Chemical Society: London, 1977; p 881.
33. (e) Simoikova, J.; Hillaire, L.; Panek, J.; Kochleofl, K. Z. Phys. Chem. FR 1973, 83, 287-304.
34. (f) Sen, B.; Vannice, M. A. J. Catal. 1988, 113, 52-71.
35. Alumina-supported Ni, Co, and Fe catalysts: (a) Narayan, S.; Unnikrishnan, R. J. Chem. Soc., Faraday Trans. 1998, 94, 1123-1128.
36. (b) Narayan, S.; Unnikrishnan, R. Stud. Surf. Sci. Catal. 1998, 113, 799-807.
37. (c) Narayan, S.; Unnikrishnan, R. Appl. Catal., A 1996, 145, 231-236.
38. Layered double hydroxide containing Co, Ni, Mg, and Al as catalysts: Unnikrishnan, R.; Narayan, S. J. Mol. Catal. 1999, 144, 173-179.
39. Activated carbon-supported Pt catalysts: Fuente, A. M.; Pulgar, G.; Gonzalez, F.; Pesquera, C.; Blanco, C. Appl. Catal., A 2001, 208, 35-46.
40. 2, or MgO as catalysts: (a) Rimar, N. N.; Pirogova, G. N. Russ. Chem. Bull. 1998, 47, 398-401.
41. (b) Pirogova, G. N.; Popova, N. N.; Voronin, Y. V. Radiochemistry 2000, 42, 565-568.
42. Zeolites containing transition-metal catalysts: (a) Melo, L.; Magnoux, P.; Giannetto, G.; Alvarez, F.; Gusinet, M. J. Mol. Catal., A 1997, 124, 155-161.
43. (b) Knifton, J. F.; Dai, P. S. E. Catal. Lett. 1999, 57, 193-197.
44. 3) as catalysts: (a) Yurieva, T. M. Catal. Today 1999, 51, 457-467.
45. (b) Yurieva, T. M. J. Mol. Catal., A 1996, 113, 455-468.
46. (c) Sakata, Y.; Nobukuni, S.; Kikumoto, E.; Tanak, K.; Imamura, H.; Tsuchiya, S. J. Mol. Catal., A 1999, 141, 269-276.
47. 15e-i are listed below. References 38 and 39 provided additional systems, many of which probe the underlying mechanisms of ketone hydrogenation. (a) Chin, C. S.; Park, S. C. Bull. Korean Chem. Soc. 1988, 9, 260-261.
48. (b) Geraty, S. M.; Harkin, P.; Vos, J. G. Inorg. Chim. Acta 1987, 131, 217-220.
49. (c) Harman, W. D.; Taube, H. J. Am. Chem. Soc. 1990, 112, 2261.
50. (d) Shafiq, F.; Eisenberg, R. J. Organomet. Chem. 1994, 472, 337-345.
51. (e) Haack, K. J.; Hashiguchi, S.; Fuji, A.; Ikeriya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285-288.
52. (f) Noyori, R., Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97.
53. (g) Matsumura, K.; Hashiguchi, S.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738.
54. (h) Yamakawa, M.; Ito, M.; Noyori, R. J. Am. Chem. Soc. 2000, 122, 1466.
55. (i) Noyori, R., Yamakawa, M.; Hashiguchi, S. J. Org Chem. 2001, 66, 7931.
56. 22 Schmid, G.; Harms, M.; Malm, J. O.; Bovin, J. O.; van Ruitenbeck, J.; Zandbergen, H. W.; Fu, W. T. J. Am. Chem. Soc. 1993, 115, 2046.
57. Representative reviews or papers on nanocluster catalysis: (a) Templeton, A. C.; Wuelfing, W. P.; Murray, R. W. Acc. Chem. Res. 2000, 33, 27.
58. (b) Rao, C. N. R.; Kulkarni, G. U.; Thomas, P. J.; Edwards, P. P. Chem. Soc. Rev. 2000, 29, 27.
59. (c) Schmid, G.; Baumle, M.; Geerkens, M.; Heim, I.; Osemann, C.; Sawitowski, T. Chem. Soc. Rev. 1999, 28, 179.
60. (d) Stein, J.; Lewis, L. N.; Gao, Y.; Scott, R. A. J. Am. Chem. Soc. 1999, 121, 3693.
61. (e) Reetz, M. T.; Breinbauer, R.; Wedemann, P.; Binger, P. Tetrahedron 1998, 54, 1233.
62. (f) Schmidt, T. J.; Noeske, M.; Gasteiger, H. A.; Behm, R. J.; Britz, P.; Brijoux, W.; Bönnemann, H. Langmuir 1997, 13, 2591.
63. (g) Schmid, G.; Maihack, V.; Lantermann, F.; Peschel, S. J. Chem. Soc., Dalton Trans. 1996, 589.
64. (h) Reetz, M. T.; Breinbauer, R.; Wanninger, K. Tetrahedron Lett. 1996, 37, 4499.
65. (i) Reetz, M. T.; Quaiser, S. A.; Merk, C. Chem. Ber. 1996, 129, 741.
66. (j) Bönnemann, H.; Braun, G. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1992.
67. (k) Lewis, L. N. Chem. Rev. 1993, 93, 2693.
68. For two introductory reviews, lead references to earlier reviews, and needed definitions (e.g., of modern transition-metal nanoclusters vs, for example, classical colloids), see: (a) Aiken, J. D., III; Finke, R. G. J. Mol. Catal. A 1999, 145, 1.
69. (b) Aiken, J. D., III; Lin, Y.; Finke, R. G. J. Mol. Catal. A 1996, 114, 29-51.
70. (c) Finke, R. G. In Metal Nanoparticles: Synthesis, Characterization and Applications; Feldheim, D. L., Foss, C. A., Jr., Eds.; Marcel Dekker: New York, 2002; Chapter 2, pp 17-54 (Transition-Metal Nanoclusters: Solution-Phase Synthesis, then Characterization and Mechanism of Formation, of Polyoxoanion- and Tetrabutylammonium-Stabilized Nanoclusters).
71. Reviews (see also ref 18): (a) Bönnemann, H.; Richards, R. Eur. J. Inorg. Chem. 2001, 2455.
72. (b) Schmid, G.; Baumle, M.; Geerkens, M.; Heim, I.; Osemann, C.; Sawitowski, T. Chem. Soc. Rev. 1999, 28, 179.
73. (c) Schmid, G.; Chi, L. F. Adv. Mater. 1998, 10, 515.
74. (d) Pendler, J. H., Ed. Nanoparticles and Nanostructured Films; Wiley-VCH: Weinheim, Germany, 1998.
75. (e) Fürstner, A., Ed. Active Metals: Preparation, Characterization, and Applications; VCH: Weinheim, Germany, 1996.
76. (f) Bradley, J. S. In Clusters and Colloids. From Theory to Applications; Schmid, G., Ed.; VCH: New York, 1994; pp 459-544.
77. (g) Schmid, G. Chem. Rev. 1992, 92, 1709.
78. (h) A superb series of papers is available in Faraday Discuss. 1991, 92, 1-300.
79. (i) Schmid, G. In Aspects of Homogeneous Catalysis; Ugo, R., Ed.; Kluwer: Dordrecht, The Netherlands, 1990; Chapter 1.
80. (j) Andres, R. P.; Averback, R. S.; Brown, W. L.; Brus, L. E.; Goddard, W. A.; Kaldor, A.; Louie S. G.; Moscovits, M.; Peercy, P. S.; Riley, S. J.; Siegel, R. W.; Spaepen, F.; Wang, Y. J. Mater. Res. 1989, 4, 704.
81. (k) Henglein, A. Chem. Rev. 1989, 89, 1861.
82. (l) Thomas, J. M. Pure Appl. Chem. 1988, 60, 1517.
83. (m) Jena, P.; Rao B. K.; Khanna, S. N. Physics and Chemistry of Small Clusters; Plenum: New York, 1987.
84. See ref 18 for a review of nanocluster catalysis which includes necessary key terms and definitions of nanoclusters vs traditional (nano-) colloids, monodisperse (±0% size distribution) and near-monodisperse (≤±15% size distribution) nanoparticles, and "magic number" (i.e., full shell and thus enhanced stability) nanoclusters, Schwartz's updated definition of homogeneous vs heterogeneous catalysts, and definitions of inorganic ("charge") and organic ("steric") stabilization mechanisms for colloids and nanoparticles.
85. Acetone as well as acetonitrile hydrogenation by both Ir and Rh nanoclusters was first noted in footnote 27 and Table B in Aiken, J. D., III; Finke, R. G. Chem. Mater. 1999, 11, 1035.
86. (a) Özkar, S.; Finke, R. G. J. Am. Chem Soc. 2001, 124, 5796.
87. (b) Özkar, S.; Finke, R. G. Langmuir 2002, 18, 7653-7662.
88. Basic Research Needs For the Hydrogen Economy; Report of the Basic Energy Sciences Workshop on Hydrogen Production, Storage and Use, May 13-15, 2003; Office of Science, U.S. Department of Energy: Washington, DC, 2003; www.sc.doe.gov/bes/hydrogen.pdf.
89. Lin, Y.; Finke, R. G. J. Am. Chem. Soc. 1994, 116, 8335.
90. Lin, Y.; Finke, R. G. Inorg. Chem. 1994, 33, 4891.
91. 26b
92. (b) Aiken, J. D., III; Finke, R. G. J. Am. Chem. Soc. 1998, 120, 9545.
93. For a review of Williamson ether synthesis, see: Staude, E.; Patat, F. In The Chemistry of the Ether Linkage; Patai, R., Ed.; Wiley: New York, 1967; pp 22-46.
94. -1 and TTO ≈ 188000 × 11 = ∼2000000.
95. (b) Hornstein, B. J.; Aiken, J. D., III; Finke, R. G. Inorg. Chem. 2002, 41, 1625.
96. 2), a mechanism that is proving to be quite general for transition-metal particle formation under reducing conditions, see: (a) Watzky, M. A.; Finke, R. G. J. Am. Chem. Soc. 1997, 119, 10382 and references therein.
97. (b) Watzky, M. A.; Finke, R. G.; Chem. Mater. 1997, 9, 3083.
98. (c) Aiken, J. D., III; Finke, R. G. J. Am. Chem. Soc. 1998, 120, 9545 and references therein to diffusive agglomeration of nanoparticles.
99. (d) Widegren, J. A.; Aiken, J. D., III; Özkar, S.; Finke, R. G. Chem. Mater. 2001, 13, 312, and references therein.
100. Adelman, R. L. J. Am. Chem. Soc. 1953, 75, 2678.
101. One caveat on the lifetime measurements: when the presence of a bulk metal precipitate is noted, the TTOs given in Table 1 or in the main text are an upper limit to the TTOs due to nanoclusters alone and as indicated by placing the TTO number in brackets, [TTOs]. See also Table 1, p 4900, in ref 25 for data showing that any bulk metal present generally has a considerably lower surface area in comparison to that of the nanoclusters and, therefore, a significantly slower rate of hydrogenation than the nanoclusters-a fortunate situation that helps limit (the still nonzero, however) contribution of bulk metal to the observed TTO number.
102. Proton Sponge: (a) Brzezinski, B.; Schroeder, G.; Grech, E.; Malarski, Z.; Sobczyk, L. J. Mol. Struct. 1992, 274, 75.
103. (b) Brzezinski, B.; Glowiak, T.; Grech, E.; Malarski, Z.; Sobczyk, L. J. Chem. Soc., Perkin Trans. 1991, 2, 1643.
104. - nanocolloids: Köhler, J. U.; Bradley, J. S. Catal. Lett. 1997, 45, 203.
105. 2 catalyzed by a series of 10 different batches of the Pd colloids: Willner, I.; Mandler, D. J. Am. Chem. Soc. 1989, 111, 1330.
106. Hornstein, B. J.; Finke, R. G. Chem. Mater. 2003, 15, 899-909.
107. Reetz, M. T.; Lohmer, G. J. Chem. Soc., Chem. Commun. 1996, 1921-1922.
108. +.
109. Yamashita, M.; Kawamura, T.; Suzuki, M.; Saito, M. Bull. Chem. Soc. Jpn. 1991, 64, 272.
110. (a) Bullock, R. M.; Song, J.-S. J. Am. Chem. Soc. 1994, 116, 8602.
111. (b) Bullock, R. M.; Luan, L.; Song, J.-S. J. Org. Chem. 1995, 60, 7170.
112. (c) Bullock, R. M.; Voges, M. H. J. Am. Chem. Soc. 2000, 122, 12594.
113. (d) Voges, M. H.; Bullock, R. M. J. Chem. Soc., Dalton Trans. 2002, 759.
114. (e) Song, J.-S.; Szalda, D. J.; Bullock, R. M. Organometallics 2001, 20, 3337.
115. (f) Bullock, M. R.; Schlaf, M.; Hauptman, E. M. US Patent 6,462,206, Oct 8, 2002.
116. (g) Bullock, M. R.; Kimmich, B. F.; Fagan, P. J.; Hauptman, E. M. US Patent 6,613,923, Sept 2, 2003.
117. (a) Tooley, P. S.; Ovalles, C.; Kao, S. C.; Darensbourg, D. J.; Darensbourg, M. Y. J. Am. Chem. Soc. 1986, 108, 5465.
118. (b) Song, J.-S.; Szalda, D. J.; Bullock, R. M.; Lawrie, C. J. C.; Rodkin, M. A:; Norton, J. R., Angew. Chem., Int. Ed. Engl. 1992, 31, 1233.
119. (c) Smith, K.-T.; Norton, J. R.; Tilset, M. Organometallics 1996, 15, 4515.
120. (d) McGee, M. P.; Norton, J. R. J. Am. Chem. Soc. 2001, 123, 1778.
121. (e) Casey, C. P.; Singer, S. W.; Powell, D. R.; Hayashi, R. K.; Kavana, M. J. Am. Chem. Soc. 2001, 123, 1090.
122. Gordon, A. J.; Ford, R. A. The Chemist's Companion, A Handbook of Practical Data, Techniques and References; Wiley-Interscience: New York, 1972; p 60.
123. 34
124. (b) Li, Y.; El-Sayed, M. A. J. Phys. Chem. B 2001, 105, 8938.
125. (c) Narayanan, R.; El-Sayed, M. A. J. Am. Chem. Soc. 2003, 125, 8340.
126. 33 system where the true catalyst is not known for certain, is Beller, M.; Fischer, H.; Kühlein, K.; Reisinger, C.-P.; Herrmann, W. A. J. Organomet. Chem. 1996, 520, 257.
127. 2/h, ca. 2-fold faster than in the absence of SBA-15.
128. Poliakoff, M.; Fitzpatrick, J. M.; Farren, T. R.; Anastas, P. T. Science 2002, 297, 807.
129. Finney, E. E; Ozkar, S.; Finke, R. G. Unpublished results and experiments in progress.
130. A few lead references to the more extensive area of C-X bond hydrodehalogenation/remediation: (a) Richmond, T. G. Top. Organomet. Chem. 1999, 3, 243-269.
131. (b) Schrick, B.; Blough, J. L.; Jones, A. D.; Mallouk, T. E. Chem. Mater. 2002, 14, 5140-5147.
132. (c) Oxley, J. D.; Suslick, K. S. Presented at the 225th ACS National Meeting, Nfcw Orleans, LA, 2003; Paper INOR-072. See also: Oxley, J. D.; Mdleleni, M.; Suslick, K. S. Presented at the 224th ACS National Meeting, Boston, MA, 2002; Paper INOR-100.
133. (c) Oxley, J. D.; Suslick, K. S. Presented at the 225th ACS National Meeting, Nfcw Orleans, LA, 2003; Paper INOR-072. See also: Oxley, J. D.; Mdleleni, M.; Suslick, K. S. Presented at the 224th ACS National Meeting, Boston, MA, 2002; Paper INOR-100.
134. (d) Yu, H.; Kennedy, E. M.; Azhar U., M.; Dlugogorski, B. Z. Appl. Catal., B 2003, 44 (3), 253-261.
135. (e) Park, C.; Menini, C.; Valverde, J. L.; Keane, M. A. J. Catal 2002, 211 (2), 451-463.
136. (a) Oxley, J. D.; Mdleleni, M. M.; Suslick, K. S. Catal. Today 2004, 88 (3-4), 139-151.
137. (b) Sonochemical preparation of the metal carbides: Suslick, K. S.; Hyeon, Fang, M. Chem. Mater. 1996, 8, 2127.
138. 47d However, at present such a recycled acetone and propene process is not of commercial interest, it appears, due to the fact that the acetone can be sold as long as the price is low enough. This situation could change in the future, however, making a process that recycles some of the acetone of future interest,
139. (b) Kirk Othmer Encyclopedia of Chemical Technology, 4th ed.; Wiley: New York, 1996; Vol. 18, pp 592-602.
140. 2O as the oxidant.
141. 2 epoxidation of propene.
142. (a) Jaska, C. A.; Manners, I. J. Am. Chem. Soc. 2004, 126, 9776.
143. 2 as a Function of Temperature and Hydrogen Pressure. J. Am. Chem. Soc. 2005, in press.
144. Woehrle, G. H.; Hutchison, J. E.; Özkar, S.; Finke, R. G. Computer-Based, Statistically Valid Analysis of Nanoparticle Transmission Electron Microscopy Data Using a Public Domain Image-Processing Program, Image. Mater. Charact., submitted for publication.
145. Press, W. H.; Flannery, B. P.; Teukolsky, S. A.; Vetterling, W. T. Numerical Recipes; Cambridge University: Cambridge, U.K., 1989.
146. Aplin, R. T.; Budzikiewicz, H.; Djerassi, C. J. Am. Chem. Soc. 1965, 87, 3180.