Benzene selectivity in competitive arene hydrogenation: Effects of single-site catalyst···acidic oxide surface binding geometry

Journal of the American Chemical Society

Volumn 137, Issue 21, 2015, Pages 6770-6780

  Gu, Weixing ^a   Stalzer, Madelyn Marie ^a   Nicholas, Christopher P ^b   Bhattacharyya, Alak ^b   Motta, Alessandro ^c   Gallagher, James R ^d   Zhang, Guanghui ^d   Miller, Jeffrey T ^d   Kobayashi, Takeshi ^e   Pruski, Marek ^e,f   Delferro, Massimiliano ^a   Marks, Tobin J ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

^b UOP LLC   (United States)

^c SAPIENZA UNIVERSITY OF ROME   (Italy)

^d ARGONNE NATIONAL LABORATORY   (United States)

^e IOWA STATE UNIVERSITY   (United States)

^f IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CATALYSTS; HYDROGENATION; LIGHT POLARIZATION; MIXTURES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANOMETALLICS; ZIRCONIUM ALLOYS;

ARENE HYDROGENATION; BENZENE HYDROGENATION; BENZENE SELECTIVITY; COMPUTATIONAL STUDIES; SELECTIVE HYDROGENATION; SINGLE-SITE CATALYSTS; SOLID-STATE NMR SPECTROSCOPY; SURFACE ORGANOMETALLIC;

CATALYST SELECTIVITY;

1,3,5 TRIMETHYLBENZENE; 6 N [2 (3,5 DIMETHOXYPHENYL) 2 (2 METHYLPHENYL)ETHYL]ADENOSINE; BENZENE; ELECTROPHILE; ETHYLBENZENE; ORGANOMETALLIC COMPOUND; OXIDE; POLYCYCLIC AROMATIC HYDROCARBON; TOLUENE;

ARTICLE; CARCINOGENICITY; CATALYST; CHEMICAL ANALYSIS; DENSITY FUNCTIONAL THEORY; ELECTROPHILICITY; HYDROGENATION; HYDROGENOLYSIS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLID STATE; SUBSTRATE CONCENTRATION; SURFACE PROPERTY;

EID: 84930661646     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b03254     Document Type: Article

References (140)

1. Stalzer, M. M.; Delferro, M.; Marks, T. J. Catal. Lett. 2015, 145, 3-14
2. Wegener, S. L.; Marks, T. J.; Stair, P. C. Acc. Chem. Res. 2012, 45, 206-214
3. Askevold, B.; Roesky, H. W.; Schneider, S. ChemCatChem 2012, 4, 307-320
4. Rascon, F.; Wischert, R.; Coperet, C. Chem. Sci. 2011, 2, 1449-1456
5. Sautet, P.; Delbecq, F. Chem. Rev. 2010, 110, 1788-1806
6. Coperet, C. Chem. Rev. 2010, 110, 656-680
7. Guzman, J.; Gates, B. C. Dalton Trans. 2003, 3303-3318
8. Copéret, C.; Chabanas, M.; Petroff Saint-Arroman, R.; Basset, J.-M. Angew. Chem., Int. Ed. 2003, 42, 156-181
9. Williams, L. A.; Marks, T. J. ACS Catal. 2011, 1, 238-245
10. Williams, L. A.; Marks, T. J. Organometallics 2009, 28, 2053-2061
11. Nicholas, C. P.; Marks, T. J. Nano Lett. 2004, 4, 1557-1559
12. Nicholas, C. P.; Marks, T. J. Langmuir 2004, 20, 9456-9462
13. Nicholas, C. P.; Ahn, H.; Marks, T. J. J. Am. Chem. Soc. 2003, 125, 4325-4331
14. Ahn, H.; Nicholas, C. P.; Marks, T. J. Organometallics 2002, 21, 1788-1806
15. Ahn, H.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 13533-13534
16. Joubert, J.; Delbecq, F.; Coperet, C.; Basset, J. M.; Sautet, P. Top. Catal. 2008, 48, 114-119
17. Motta, A.; Fragala, I. L.; Marks, T. J. J. Am. Chem. Soc. 2008, 130, 16533-16546
18. Jezequel, M.; Dufaud, V.; Ruiz-Garcia, M. J.; Carrillo-Hermosilla, F.; Neugebauer, U.; Niccolai, G. P.; Lefebvre, F.; Bayard, F.; Corker, J.; Fiddy, S.; Evans, J.; Broyer, J. P.; Malinge, J.; Basset, J.-M. J. Am. Chem. Soc. 2001, 123, 3520-3540
19. Eisen, M. S.; Marks, T. J. J. Mol. Catal. 1994, 86, 23-50
20. Marks, T. J. Acc. Chem. Res. 1992, 25, 57-65
21. Tovar, T. M.; Stewart, S. M.; Scott, S. L. Top. Catal. 2012, 55, 530-537
22. Lee, M.-Y.; Scott, S. L. Chem.-Eur. J. 2011, 17, 4632-4639
23. Moses, A. W.; Raab, C.; Nelson, R. C.; Leifeste, H. D.; Ramsahye, N. A.; Chattopadhyay, S.; Eckert, J.; Chmelka, B. F.; Scott, S. L. J. Am. Chem. Soc. 2007, 129, 8912-8920
24. Scott, S. L.; Church, T. L.; Nguyen, D. H.; Mader, E. A.; Moran, J. Top. Catal. 2005, 34, 109-120
25. Ajjou, J. A. N.; Scott, S. L. J. Am. Chem. Soc. 2000, 122, 8968-8976
26. Zhizhko, P. A.; Zhizhin, A. A.; Belyakova, O. A.; Zubavichus, Y. V.; Kolyagin, Y. G.; Zarubin, D. N.; Ustynyuk, N. A. Organometallics 2013, 32, 3611-3617
27. Chen, Y.; Credendino, R.; Callens, E.; Atiqullah, M.; Al-Harthi, M. A.; Cavallo, L.; Basset, J.-M. ACS Catal. 2013, 3, 1360-1364
28. Samantaray, M. K.; Alauzun, J.; Gajan, D.; Kavitake, S.; Mehdi, A.; Veyre, L.; Lelli, M.; Lesage, A.; Emsley, L.; Coperet, C.; Thieuleux, C. J. Am. Chem. Soc. 2013, 135, 3193-3199
29. Popoff, N.; Espinas, J.; Pelletier, J.; Szeto, K. C.; Thivolle-Cazat, J.; Delevoye, L.; Gauvin, R. M.; Taoufik, M. ChemCatChem 2013, 5, 1971-1977
30. Mori, K.; Watanabe, K.; Terai, Y.; Fujiwara, Y.; Yamashita, H. Chem.-Eur. J. 2012, 18, 11371-11378
31. Le, R. E.; Liang, Y.; Tornroos, K. W.; Nief, F.; Anwander, R. Organometallics 2012, 31, 6526-6537
32. Chen, Y.; Callens, E.; Abou-Hamad, E.; Merle, N.; White, A. J. P.; Taoufik, M.; Coperet, C.; Le, R. E.; Basset, J.-M. Angew. Chem., Int. Ed. 2012, 51, 11886-11889
33. Bonati, M. L. M.; Douglas, T. M.; Gaemers, S.; Guo, N. Organometallics 2012, 31, 5243-5251
34. Szeto, K. C.; Hardou, L.; Merle, N.; Basset, J.-M.; Thivolle-Cazat, J.; Papaioannou, C.; Taoufik, M. Catal. Sci. Technol. 2012, 2, 1336-1339
35. Solans-Monfort, X.; Chow, C.; Goure, E.; Kaya, Y.; Basset, J.-M.; Taoufik, M.; Quadrelli, E. A.; Eisenstein, O. Inorg. Chem. 2012, 51, 7237-7249
36. Espinas, J.; Pelletier, J. D. A.; Abou-Hamad, E.; Emsley, L.; Basset, J.-M. Organometallics 2012, 31, 7610-7617
37. Popoff, N.; Espinas, J.; Goure, E.; Boyron, O.; Le, R. E.; Basset, J.-M.; Gauvin, R. M.; de Mallmann, A.; Taoufik, M. Macromol. Rapid Commun. 2011, 32, 1921-1924
38. Polshettiwar, V.; Thivolle-Cazat, J.; Taoufik, M.; Stoffelbach, F.; Norsic, S.; Basset, J.-M. Angew. Chem., Int. Ed. 2011, 50, 2747-2751
39. Pelletier, J.; Espinas, J.; Vu, N.; Norsic, S.; Baudouin, A.; Delevoye, L.; Trebosc, J.; Le, R. E.; Santini, C.; Basset, J.-M.; Gauvin, R. M.; Taoufik, M. Chem. Commun. 2011, 47, 2979-2981
40. Goure, E.; Avenier, P.; Solans-Monfort, X.; Veyre, L.; Baudouin, A.; Kaya, Y.; Taoufik, M.; Basset, J.-M.; Eisenstein, O.; Quadrelli, E. A. New J. Chem. 2011, 35, 1011-1019
41. Legagneux, N.; Jeanneau, E.; Thomas, A.; Taoufik, M.; Baudouin, A.; de Mallmann, A.; Basset, J.-M.; Lefebvre, F. Organometallics 2011, 30, 1783-1793
42. Tosin, G.; Delgado, M.; Baudouin, A.; Santini, C. C.; Bayard, F.; Basset, J.-M. Organometallics 2010, 29, 1312-1322
43. Szeto, K. C.; Norsic, S.; Hardou, L.; Le, R. E.; Chakka, S.; Thivolle-Cazat, J.; Baudouin, A.; Papaioannou, C.; Basset, J. M.; Taoufik, M. Chem. Commun. 2010, 46, 3985-3987
44. Mazoyer, E.; Merle, N.; de Mallmann, A.; Basset, J.-M.; Berrier, E.; Delevoye, L.; Paul, J.-F.; Nicholas, C. P.; Gauvin, R. M.; Taoufik, M. Chem. Commun. 2010, 46, 8944-8946
45. Maury, O.; Lefort, L.; Vidal, V.; Thivolle-Cazat, J.; Basset, J.-M. Organometallics 2010, 29, 6612-6614
46. Popoff, N.; Gauvin, R. M.; De Mallmann, A.; Taoufik, M. Organometallics 2012, 31, 4763-4768
47. Millot, N.; Soignier, S.; Santini, C. C.; Baudouin, A.; Basset, J. M. J. Am. Chem. Soc. 2006, 128, 9361-9370
48. Williams, L. A.; Guo, N.; Motta, A.; Delferro, M.; Fragala, I. L.; Miller, J. T.; Marks, T. J. Proc. Natl. Acad. Sci. U. S. A. 2013, 110, 413-418
49. The average distance found in the Cambridge Crystallographic Data Centre (CCDC, May 2014) for Zr-O single bonds is 1.988 (±12).
50. Serna, P.; Gates, B. C. Acc. Chem. Res. 2014, 47, 2612-2620
51. Jia, H.-P.; Quadrelli, E. A. Chem. Soc. Rev. 2014, 43, 547-564
52. Conley, M. P.; Coperet, C.; Thieuleux, C. ACS Catal. 2014, 4, 1458-1469
53. Mondloch, J. E.; Wang, Q.; Frenkel, A. I.; Finke, R. G. J. Am. Chem. Soc. 2010, 132, 9701-9714
54. Liu, G.; Yao, M.; Wang, J.; Lu, X.; Liu, M.; Zhang, F.; Li, H. Adv. Synth. Catal. 2008, 350, 1464-1468
55. Warad, I.; Eichele, K.; Mayer, H. A.; Lindner, E. Inorg. Chim. Acta 2004, 357, 1847-1853
56. Raja, R.; Thomas, J. M.; Jones, M. D.; Johnson, B. F. G.; Vaughan, D. E. W. J. Am. Chem. Soc. 2003, 125, 14982-14983
57. Giordano, R.; Serp, P.; Kalck, P.; Kihn, Y.; Schreiber, J.; Marhic, C.; Duvail, J.-L. Eur. J. Inorg. Chem. 2003, 610-617
58. Hamdemir, I. K.; Ozkar, S.; Finke, R. G. J. Mol. Catal. A: Chem. 2013, 378, 333-343
59. Hamdemir, I. K.; Ozkar, S.; Yih, K.-H.; Mondloch, J. E.; Finke, R. G. ACS Catal. 2012, 2, 632-641
60. Yih, K.-H.; Alley, W. M.; Finke, R. G. Organometallics 2011, 30, 5068-5070
61. Alley, W. M.; Hamdemir, I. K.; Wang, Q.; Frenkel, A. I.; Li, L.; Yang, J. C.; Menard, L. D.; Nuzzo, R. G.; Ozkar, S.; Yih, K.-H.; Johnson, K. A.; Finke, R. G. Langmuir 2011, 27, 6279-6294
62. Alley, W. M.; Hamdemir, I. K.; Wang, Q.; Frenkel, A. I.; Li, L.; Yang, J. C.; Menard, L. D.; Nuzzo, R. G.; Ozkar, S.; Johnson, K. A.; Finke, R. G. Inorg. Chem. 2010, 49, 8131-8147
63. Alley, W. M.; Hamdemir, I. K.; Johnson, K. A.; Finke, R. G. J. Mol. Catal. A: Chem. 2010, 315, 1-27
64. Alley, W. M.; Girard, C. W.; Ozkar, S.; Finke, R. G. Inorg. Chem. 2009, 48, 1114-1121
65. Shamshoum, E. S.; Rauscher, D. J. US5739220A, 1998.
66. Koritala, S. US176235A0, 1981.
67. Cox, J. L.; Wilcox, W. A. US863765, 1980.
68. Kroll, W. R. GB1117319, 1968.
69. Kroll, W. R. US3323902, 1967.
70. Directive 98/69/EC of the European Parliament and of the Council of 13 October 1998, Official Journal of the European Communities, 28.12.98, L350, pp 1-56.
71. EPA MSAT2 regulation, 72 FR 8428; 2/26/07.
72. Canada SOR/97-493.
73. Australian Fuel Standard (Petrol) Determination 2001 as amended by the Fuel Standard (Petrol) Amendment Determination 2008, (no. 1).
74. Prior to 1 Jan 2011, US gasoline contained an average of 0.97 vol % benzene.
75. Harley, R. A.; Hooper, D. S.; Kean, A. J.; Kirchstetter, T. W.; Hesson, J. M.; Balberan, N. T.; Stevenson, E. D.; Kendall, G. R. Environ. Sci. Technol. 2006, 40, 5084-5088
76. Nikolaev, V. F.; Tabrisov, I. I.; Penkovsky, A. I.; Sultanova, R. B. Fuel 2015, 142, 94-101
77. Frysinger, G. S.; Gaines, R. B.; Ledford, E. B. J. High Resolut. Chromatogr. 1999, 22, 195-200
78. Meister, J.; Crowe, T.; Keesom, W.; Stine, M. Oil Gas J. 2006, 104, 38-45
79. Dinkov, R.; Stratiev, D.; Chomakov, M.; Kirilov, K. Pet. Coal 2008, 50, 56-62
80. Peer, R. L.; Bennett, R. W.; Felch, D. E.; von Schmidt, E. Catal. Today 1993, 18, 473-486
81. Lee, F. M.; Gentry, J. C. Chem. Eng. Prog. 1997, 93, 56-64
82. Bartholomew, C. H.; Farrauto, R. J. In Fundamentals of Industrial Catalytic Processes, 2 nd ed.; John Wiley & Sons, Inc.: Hoboken, NJ, 2006; pp 1-970.
83. Kim, W.; Kim, J.-C.; Kim, J.; Seo, Y.; Ryoo, R. ACS Catal. 2013, 3, 192-195
84. Laredo, G. C.; Castillo, J. J.; Navarrete-Bolanos, J.; Perez-Romo, P.; Lagos, F. A. Appl. Catal., A 2012, 413-414, 140-148
85. Sakuneka, T. M.; Nel, R. J. J.; de Klerk, A. Ind. Eng. Chem. Res. 2008, 47, 7178-7183
86. Hsieh, C. R.; Robinson, R. C. Process to remove benzene from refinery streams. US5210348A, 1993.
87. Nicholas, C. P.; Bhattacharyya, A. US8895793, 2014;.
88. Hsieh, C. R.; Robinson, R. C. US5210348A, 1993.
89. Mashkovsky, I. S.; Baeva, G. N.; Stakheev, A. Y.; Voskoboynikov, T. V.; Barger, P. T. Mendeleev Commun. 2009, 19, 108-109
90. Ramadhan, O. M.; Al-Hyali, E. A. Pet. Sci. Technol. 1999, 17, 623-635
91. Zhou, G.; Pei, Y.; Jiang, Z.; Fan, K.; Qiao, M.; Sun, B.; Zong, B. J. Catal. 2014, 311, 393-403
92. Youngs, T. G. A.; Manyar, H.; Bowron, D. T.; Gladden, L. F.; Hardacre, C. Chem. Sci. 2013, 4, 3484-3489
93. Bayram, E.; Finke, R. G. ACS Catal. 2012, 2, 1967-1975
94. Tsai, K.-Y.; Wang, I.; Tsai, T.-C. Catal. Today 2011, 166, 73-78
95. Liu, H.; Jiang, T.; Han, B.; Liang, S.; Wang, W.; Wu, T.; Yang, G. Green Chem. 2011, 13, 1106-1109
96. Bayram, E.; Linehan, J. C.; Fulton, J. L.; Roberts, J. A. S.; Szymczak, N. K.; Smurthwaite, T. D.; Ozkar, S.; Balasubramanian, M.; Finke, R. G. J. Am. Chem. Soc. 2011, 133, 18889-18902
97. Zahmakiran, M.; Tonbul, Y.; Ozkar, S. J. Am. Chem. Soc. 2010, 132, 6541-6549
98. Belskaya, O. B.; Danilova, I. G.; Kazakov, M. O.; Gulyaeva, T. I.; Kibis, L. S.; Boronin, A. I.; Lavrenov, A. V.; Likholobov, V. A. Appl. Catal., A 2010, 387, 5-12
99. Bayram, E.; Zahmakiran, M.; Ozkar, S.; Finke, R. G. Langmuir 2010, 26, 12455-12464
100. Keane, M. A.; Patterson, P. M. J. Chem. Soc., Faraday Trans. 1996, 92, 1413-1421
101. Poondi, D.; Albert Vannice, M. J. Catal. 1996, 161, 742-751
102. Hino, M.; Arata, K. J. Chem. Soc., Chem. Commun. 1988, 1259-1260
103. Hollstein, E. J.; Hsu, C.; Wei, J. T. US4956519A, 1990.
104. Arata, K. In Preparation of Superacidic Metal Oxides and Their Catalytic Action; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2009; pp 665-704.
105. Norsic, S.; Larabi, C.; Delgado, M.; Garron, A.; de Mallmann, A.; Santini, C.; Szeto, K. C.; Basset, J.-M.; Taoufik, M. Catal. Sci. Technol. 2012, 2, 215-219
106. Tosin, G.; Santini, C. C.; Basset, J.-M. Top. Catal. 2009, 52, 1203-1210
107. Chabanas, M.; Vidal, V.; Copéret, C.; Thivolle-Cazat, J.; Basset, J.-M. Angew. Chem., Int. Ed. 2000, 39, 1962-1965
108. Rosier, C.; Niccolai, G. P.; Basset, J.-M. J. Am. Chem. Soc. 1997, 119, 12408-12409
109. d'Ornelas, L.; Reyes, S.; Quignard, F.; Choplin, A.; Basset, J.-M. Chem. Lett. 1993, 22, 1931-1934
110. Chen, Y.-X.; Metz, M. V.; Li, L.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 6287-6305
111. Heller, D.; Buschmann, H.; Scharf, H.-D. Angew. Chem., Int. Ed. 1996, 35, 1852-1854
112. Zamostny, P.; Belohlav, Z. Appl. Catal., A 2002, 225, 291-299
113. Chen, Y.; Abou-Hamad, E.; Hamieh, A.; Hamzaoui, B.; Emsley, L.; Basset, J.-M. J. Am. Chem. Soc. 2015, 137, 588-591
114. Althaus, S. M.; Mao, K.; Stringer, J. A.; Kobayashi, T.; Pruski, M. Solid State Nucl. Magn. Reson. 2014, 57-58, 17-21
115. Mao, K.; Kobayashi, T.; Wiench, J. W.; Chen, H.-T.; Tsai, C.-H.; Lin, V. S. Y.; Pruski, M. J. Am. Chem. Soc. 2010, 132, 12452-12457
116. Mao, K.; Wiench, J. W.; Lin, V. S. Y.; Pruski, M. J. Magn. Reson. 2009, 196, 92-95
117. Wiench, J. W.; Bronnimann, C. E.; Lin, V. S. Y.; Pruski, M. J. Am. Chem. Soc. 2007, 129, 12076-12077
118. Trebosc, J.; Wiench, J. W.; Huh, S.; Lin, V. S. Y.; Pruski, M. J. Am. Chem. Soc. 2005, 127, 7587-7593
119. Xu, J.; Zheng, A.; Yang, J.; Su, Y.; Wang, J.; Zeng, D.; Zhang, M.; Ye, C.; Deng, F. J. Phys. Chem. B 2006, 110, 10662-10671
120. Pellecchia, C.; Grassi, A.; Immirzi, A. J. Am. Chem. Soc. 1993, 115, 1160-1162
121. Lubben, T. V.; Wolczanski, P. T.; Van Duyne, G. D. Organometallics 1984, 3, 977-983
122. Haase, F.; Sauer, J. J. Am. Chem. Soc. 1998, 120, 13503-13512
123. Hofmann, A.; Sauer, J. J. Phys. Chem. B 2004, 108, 14652-14662
124. Lavanant, L.; Silvestru, A.; Faucheux, A.; Toupet, L.; Jordan, R. F.; Carpentier, J.-F. Organometallics 2005, 24, 5604-5619
125. Zuccaccia, C.; Stahl, N. G.; Macchioni, A.; Chen, M.-C.; Roberts, J. A.; Marks, T. J. J. Am. Chem. Soc. 2004, 126, 1448-1464
126. Bochmann, M.; Karger, G.; Jaggar, A. J. J. Chem. Soc., Chem. Commun. 1990, 1038-1039
127. Yuzawa, H.; Aoki, M.; Itoh, H.; Yoshida, H. J. Phys. Chem. Lett. 2011, 2, 1868-1873
128. Noor, A.; Kretschmer, W. P.; Glatz, G.; Meetsma, A.; Kempe, R. Eur. J. Inorg. Chem. 2008, 5088-5098
129. Wolczanski, P. T.; Bercaw, J. E. Organometallics 1982, 1, 793-799
130. Yang, X. M.; Stern, C. L.; Marks, T. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 1375-1377
131. Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015-10031
132. Basset, J. M.; Ugo, R. In Surface Organometallic Chemistry; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2009.
133. Cho, H.-G.; Cheong, B.-S. Bull. Korean Chem. Soc. 2009, 30, 479-481
134. Rong, Y.; Al-Harbi, A.; Parkin, G. Organometallics 2012, 31, 8208-8217
135. Chirik, P. J.; Bercaw, J. E. Organometallics 2005, 24, 5407-5423
136. Schock, L. E.; Marks, T. J. J. Am. Chem. Soc. 1988, 110, 7701-7715
137. Guerrero, A.; Martin, E.; Hughes, D. L.; Kaltsoyannis, N.; Bochmann, M. Organometallics 2006, 25, 3311-3313
138. Lin, C.-Y.; Dunbar, R. C. Organometallics 1997, 16, 2691-2697
139. Dudnik, A. S.; Weidner, V. L.; Motta, A.; Delferro, M.; Marks, T. J. Nat. Chem. 2014, 6, 1100-1107
140. Kozuch, S.; Shaik, S. Acc. Chem. Res. 2010, 44, 101-110