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Thermo-responsive Ruthenium Dendrimer-based Catalysts for Hydrogenation of the Aromatic Compounds and Phenols

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Abstract

In this work thermo-responsive ruthenium catalysts, based on the poly(propylene imine) dendrimers cross-linked with the poly(ethylene glycol) diglycidyl ether, have been prepared for the first time. The materials obtained were characterized by X-ray photoelectron spectroscopy and transmission electron microscopy, and tested in the phenol and benzene hydrogenation. Conditions for the metal impregnation into the polymeric matrix were demonstrated to have a great influence both on physical chemical properties of the synthesized catalysts (metal loading, mean particles size, surface structure etc.), and, as a consequence, on their hydrogenation activity and thermo-responsive properties.

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References

  1. A.D. Pomogailo, Catalysis by Immobilized Complexes (Nauka, Moscow, 1991)

    Google Scholar 

  2. E.A. Bekturov, S.E. Kudaibergenov, Catalysis by Polymers (Wiley, Weinheim, 2002), pp. 67–144

    Google Scholar 

  3. E.A. Karakhanov, A.G. Dedov, L.E. Tskhai, V.V. Shatalov, Pet. Chem. 33, 202 (1993)

    Google Scholar 

  4. B. Clapham, T.S. Reger, K.D. Janda, Tetrahedron 57, 4637 (2001)

    Article  CAS  Google Scholar 

  5. D.E. Bergbreiter, V.M. Mariagnanam, L. Zhang, Adv. Mater. 7, 69 (1995)

    Article  CAS  Google Scholar 

  6. S. Nlate, L. Plault, D. Astruc, Chem. Eur. J. 12, 903 (2006)

    Article  CAS  Google Scholar 

  7. X. Liu, Y. Li, G. Wang, Z. Chai, Y. Wu, G. Zhao, Tetrahedron 17, 750 (2006)

    Article  CAS  Google Scholar 

  8. M.-L. Kontkanen, M. Haukka, Catal. Commun. 23, 25 (2012)

    Article  CAS  Google Scholar 

  9. J. Potier, S. Menuel, D. Fournier, S. Fourmentin, P. Woisel, E. Monflier, F. Hapiot, ACS Catal. 2, 1417 (2012)

    Article  CAS  Google Scholar 

  10. T. Suzuki, K. Kimura, T. Nagamine, Polymers 3, 621 (2011)

    Article  CAS  Google Scholar 

  11. A. Corma, H. García, A. Leyva, J. Catal. 240, 87 (2006)

    Article  CAS  Google Scholar 

  12. A. Ohtaka, T. Teratani, R. Fujii, K. Ikeshita, O. Shimomura, R. Nomura, Chem. Commun. 46, 7188 (2009)

    Article  CAS  Google Scholar 

  13. M.V. Vasylyev, G. Maayan, Y. Hovav, A. Haimov, R. Neumann, Org. Lett. 8, 5445 (2006)

    Article  CAS  Google Scholar 

  14. F. Lu, J. Liu, J. Xu, Adv. Synth. Catal. 348, 857 (2006)

    Article  CAS  Google Scholar 

  15. Y. Nakamura, H. Hirai, Chem. Lett. 8, 823 (1975)

    Article  Google Scholar 

  16. Y. Nakamura, H. Hirai, Chem. Lett. 5, 165 (1976)

    Article  Google Scholar 

  17. R. Mani, V. Mahadevan, M. Srinivasan, J. Macromol. Sci. A 30, 557 (1993)

    Article  Google Scholar 

  18. A.L. Maksimov, S.N. Kuklin, YuS Kardasheva, E.A. Karakhanov, Pet. Chem. 53, 157 (2013)

    Article  CAS  Google Scholar 

  19. S. Kuklin, A. Maximov, A. Zolotukhina, E. Karakhanov, Catal. Commun. 73, 63 (2016)

    Article  CAS  Google Scholar 

  20. F. Lu, J. Liu, J. Xu, Mater. Chem. Phys. 108, 369 (2008)

    Article  CAS  Google Scholar 

  21. F. Lu, J. Liu, J. Xu, J. Mol. Catal. A 271, 6 (2007)

    Article  CAS  Google Scholar 

  22. X. Zhou, T. Wu, B. Hu, T. Jiang, B. Han, J Mol. Catal. A 306, 143 (2009)

    Article  CAS  Google Scholar 

  23. E. Bayer, W. Schumann, J. Chem. Soc. Chem. Comm. 12, 949 (1986)

    Article  Google Scholar 

  24. H. Hirai, H. Chawanya, N. Toshima, Makromol. Chem. Rapid Commun. 2, 99 (1981)

    Article  CAS  Google Scholar 

  25. V.N. Perchenko, G.A. Sytov, RSh Abubakirov, T.O. Omaraliev, Dokl. Akad. Nauk SSSR 282, 109 (1985)

    CAS  Google Scholar 

  26. V.N. Perchenko, I.V. Obydennova, I.M. Shanazarova, N.S. Nametkin, Izv. Akad. Nauk SSSR Ser. Khim. 3, 690 (1982)

    Google Scholar 

  27. RSh Abubakirov, G.A. Sytov, V.N. Perchenko, T.O. Omaraliev, N.S. Nametkin, Dokl. Akad. Nauk SSSR 272, 1379 (1983)

    CAS  Google Scholar 

  28. V.N. Perchenko, I.S. Kalashnikova, G.L. Kamneva, Pet. Chem. 27, 219 (1987)

    CAS  Google Scholar 

  29. Sh Mori, T. Ohkubo, T. Ikawa, A. Kume, T. Maegawa, Y. Monguchi, H. Sajiki, J. Mol. Catal. A 307, 77 (2009)

    Article  CAS  Google Scholar 

  30. A.D. Pomogailo, Polymeric Immobilized Metal Complex Catalysts (Nauka, Moscow, 1988)

    Google Scholar 

  31. G.R. Newkome, C.D. Shreiner, Polymer 49, 1 (2008)

    Article  CAS  Google Scholar 

  32. Y. Niu, R.M. Crooks, C. R. Chimie 6, 1049 (2003)

    Article  CAS  Google Scholar 

  33. R.M. Crooks, M. Zhao, L. Sun, V. Chechik, L.K. Yeung, Acc. Chem. Res. 34, 181 (2001)

    Article  CAS  Google Scholar 

  34. D. Méry, D. Astruc, Coord. Chem. Rev. 250, 1965 (2006)

    Article  CAS  Google Scholar 

  35. R. Andrés, E. de Jesús, J.C. Flores, New J. Chem. 31, 1161 (2007)

    Article  CAS  Google Scholar 

  36. E.A. Karakhanov, A.L. Maximov, A.V. Zolotukhina, S.V. Kardashev, Pet. Chem. 50, 290 (2010)

    Article  Google Scholar 

  37. G.-J. Deng, Q.-H. Fan, X.-M. Chen, D.-S. Liu, A.S.C. Chan, Chem. Commun. 15, 1570 (2002)

    Article  CAS  Google Scholar 

  38. S.-K. Oh, Y. Niu, R.M. Crooks, Langmuir 21, 10209 (2005)

    Article  CAS  Google Scholar 

  39. C. Ornelas, J.R. Aranzaes, L. Salmon, D. Astruc, Chem. Eur. J 14, 50 (2008)

    Article  CAS  Google Scholar 

  40. C. Ornelas, J. Ruiz, L. Salmon, D. Astruc, Adv. Synth. Catal. 350, 837 (2008)

    Article  CAS  Google Scholar 

  41. E.A. Karakhanov, A.L. Maximov, A.V. Zolotukhina, M.V. Terenina, A.V. Vutolkina, Nanoget. Catal. 1, 31 (2016)

    Google Scholar 

  42. A. Maximov, A. Zolotukhina, V. Murzin, E. Karakhanov, E. Rosenberg, ChemCatChem 7, 1197 (2015)

    Article  CAS  Google Scholar 

  43. M. Murata, Yu. Tanaka, T. Mizugaki, K. Ebitani, K. Kaneda, Chem. Lett. 34, 272 (2005)

    Article  CAS  Google Scholar 

  44. E.A. Karakhanov, A.L. Maksimov, E.M. Zakharian, YuS Kardasheva, S.V. Savilov, N.I. Truhmanova, A.O. Ivanov, V.A. Vinokurov, J. Mol. Catal. A 397, 1 (2015)

    Article  CAS  Google Scholar 

  45. E. Karakhanov, A. Maximov, Yu. Kardasheva, V. Semernina, A. Zolotukhina, A. Ivanov, G. Abbott, E. Rosenberg, V. Vinokurov, ACS Appl. Mater. Interfaces 6, 8807 (2014)

    Article  CAS  Google Scholar 

  46. T. Mizugaki, M. Ooe, K. Ebitani, K. Kaneda, J. Mol. Catal. A 145, 329 (1999)

    Article  CAS  Google Scholar 

  47. M. Ooe, M. Murata, T. Mizugaki, K. Ebitani, K. Kaneda, Nano Lett. 2, 999 (2002)

    Article  CAS  Google Scholar 

  48. T. Mizugaki, Y. Miyauchi, M. Murata, K. Ebitani, K. Kaneda, Chem. Lett. 34, 286 (2005)

    Article  CAS  Google Scholar 

  49. E.A. Karakhanov, A.L. Maximov, B.N. Tarasevich, V.A. Skorkin, J. Mol. Catal. A 297, 73 (2009)

    Article  CAS  Google Scholar 

  50. M. Ooe, M. Murata, T. Mizugaki, K. Ebitani, K. Kaneda, J. Am. Chem. Soc. 126, 1604 (2004)

    Article  CAS  Google Scholar 

  51. M.T. Reetz, G. Lohmer, R. Schwickardi, Angew. Chem. Inl. Ed. Engl. 36, 1526 (1997)

    Article  CAS  Google Scholar 

  52. K. Heuzé, D. Méry, D. Gauss, D. Astruc, Chem. Commun. 18, 2274 (2003)

    Article  Google Scholar 

  53. D.P. Catsoulacos, B.R. Steele, G.A. Heropoulos, M. Micha-Screttas, C.G. Screttas, Tetrahedron Lett. 44, 4575 (2003)

    Article  CAS  Google Scholar 

  54. K.R. Gopidas, J.K. Whitesell, M.A. Fox, Nano Lett. 3, 1757 (2003)

    Article  CAS  Google Scholar 

  55. M. Bernechea, E. de Jesús, C. López-Mardomingo, P. Terreros, Inorg. Chem. 48, 4491 (2009)

    Article  CAS  Google Scholar 

  56. J.C. Garcia-Martinez, R. Lezutekong, R.M. Crooks, J. Am. Chem. Soc. 127, 5097 (2005)

    Article  CAS  Google Scholar 

  57. M. Pittelkow, K. Moth-Poulsen, U. Boas, J.B. Christensen, Langmuir 19, 7682 (2003)

    Article  CAS  Google Scholar 

  58. Z. Maeno, M. Okao, T. Mitsudome, T. Mizugaki, K. Jitsukawa, K. Kaneda, RSC Adv. 3, 9662 (2013)

    Article  CAS  Google Scholar 

  59. T. Borkowski, P. Subik, A.M. Trzeciak, S. Wołowiec, Molecules 16, 427 (2011)

    Article  CAS  Google Scholar 

  60. G.V. Rakova, A.A. Shaginyan, N.S. Yenikolopyan, Polym. Sci. USSR 9, 2916 (1967)

    Article  Google Scholar 

  61. D.E. Bergbreiter, L. Zhang, V.M. Mariagnanam, J. Am. Chem. Soc. 115, 9295 (1993)

    Article  CAS  Google Scholar 

  62. U.R. Pillai, E. Sahle-Demessie, J. Mol. Catal. A 222, 153 (2004)

    Article  CAS  Google Scholar 

  63. E.A. Karakhanov, SYu. Narin, A.G. Dedov, Catal. Lett. 3, 31 (1989)

    Article  CAS  Google Scholar 

  64. E.A. Karakhanov, A.L. Maksimov, E.A. Ivanova, Russ. Chem. Bull. Int. Ed. 56, 621 (2007)

    Article  CAS  Google Scholar 

  65. E.A. Karakhanov, YuS Kardasheva, E.A. Runova, V.A. Semernina, J. Mol. Catal. A 142, 339 (1999)

    Article  CAS  Google Scholar 

  66. D. Li, J.R. Dunlap, B. Zhao, Langmuir 24, 5911 (2008)

    Article  CAS  Google Scholar 

  67. K. Kono, Polym. J. 44, 531 (2012)

    Article  CAS  Google Scholar 

  68. R.R. Ramireddy, K.R. Raghupathi, D.A. Torres, S. Thayumanavan, New J. Chem. 36, 340 (2012)

    Article  CAS  Google Scholar 

  69. S. Svenson, Chem. Soc. Rev. 44, 4131 (2015)

    Article  CAS  Google Scholar 

  70. R.M. Kannan, S. Kannan, R. Romero, R. Navath, A. Menjoge, World Patent WO 2011/123591 A1 (2011)

  71. Y. Haba, C. Kojima, A. Harada, T. Ura, H. Horinaka, K. Kono, Langmuir 23, 5243 (2007)

    Article  CAS  Google Scholar 

  72. T.R. Krishna, N. Jayaraman, Tetrahedron 60, 10325 (2004)

    Article  CAS  Google Scholar 

  73. Sh Ogasawara, Sh Kato, J. Am. Chem. Soc. 132, 4608 (2010)

    Article  CAS  Google Scholar 

  74. Y. Yang, S. Ogasawara, G. Li, S. Kato, Polym. J. 47, 1 (2015)

    Article  CAS  Google Scholar 

  75. E.A. Karakhanov, A.L. Maximov, V.A. Skorkin, A.V. Zolotukhina, A.S. Smerdov, AYu. Tereshchenko, Pure Appl. Chem. 81, 2013 (2009)

    CAS  Google Scholar 

  76. E. de Brabander van den Berg, E.W. Meijer, Angew. Chem. Int. Ed. Engl. 32, 1308 (1993)

    Article  Google Scholar 

  77. C.V. Banks, J.W. O’Laughlin, Anal. Chem. 29, 1412 (1957)

    Article  CAS  Google Scholar 

  78. J. Xu, L. Sun, J. Li, J. Liang, H. Zhang, W. Yang, Nanoscale Res. Lett. 6, 561 (2011)

    Article  Google Scholar 

  79. J.Y. Lee, J. Yang, T.C. Deivaraj, H.-P. Too, J. Colliod. Interface Sci. 268, 77 (2003)

    Article  CAS  Google Scholar 

  80. G. Beamson, D. Briggs, High Resolution XPS of Organic Polymers: the Scienta ESCA300 Database (Wiley, Chichester, 1992)

    Google Scholar 

  81. J.Y. Shen, A. Adnot, S. Kaliaguine, Appl. Surf. Sci. 51, 47 (1991)

    Article  CAS  Google Scholar 

  82. K.S. Kim, N. Winograd, J. Catal. 35, 66 (1974)

    Article  CAS  Google Scholar 

  83. B. Folkesson, Acta Chem. Scand. 27, 287 (1973)

    Article  CAS  Google Scholar 

  84. V.I. Nefedov, Koord. Khim. 4, 1285 (1978)

    Google Scholar 

  85. D.T. Clark, I.S. Woolsey, S.D. Robinson, K.R. Laing, J.N. Wingfield, Inorg. Chem. 16, 1201 (1977)

    Article  CAS  Google Scholar 

  86. Y.I. Kim, W.E. Hatfield, Inorg. Chim. Acta 188, 15 (1991)

    Article  CAS  Google Scholar 

  87. D.A. Geselowitz, W. Kutner, T.J. Meyer, Inorg. Chem. 25, 2015 (1986)

    Article  CAS  Google Scholar 

  88. M.M.T. Khan, S. Srivastava, Polyhedron 7, 1063 (1988)

    Article  CAS  Google Scholar 

  89. J.J. Chen, N. Winograd, Surf. Sci. 326, 285 (1995)

    Article  CAS  Google Scholar 

  90. S. Puniyani, T.S. Srivastava, Inorg. Chim. Acta 131, 95 (1987)

    Article  CAS  Google Scholar 

  91. J. Okal, Mater. Res. Bull. 44, 318 (2009)

    Article  CAS  Google Scholar 

  92. S. Hosokawa, H. Kanai, K. Utani, Y. Taniguchi, Y. Saito, S. Imamura, Appl. Catal. B 45, 181 (2003)

    Article  CAS  Google Scholar 

  93. H. Schulenburg, M. Hilgendorff, I. Dorbandt, J. Radnik, P. Bogdanoff, S. Fiechter, M. Bron, H. Tributsch, J. Power Sources 155, 47 (2006)

    Article  CAS  Google Scholar 

  94. I. Toyoshima, G.A. Somorjai, Catal. Rev. Sci. Eng. 19, 105 (1979)

    Article  CAS  Google Scholar 

  95. E.A. Karakhanov, A.L. Maximov, A.V. Zolotukhina, TYu. Filippova, S.V. Kardashev, Pet. Chem. 52, 289 (2012)

    Article  CAS  Google Scholar 

  96. U. Schlotterbeck, C. Aymonier, R. Thomann, H. Hofmeister, M. Tromp, W. Richtering, S. Mecking, Adv. Func. Mater. 14, 999 (2004)

    Article  CAS  Google Scholar 

  97. G. Férey, C. Serre, Chem. Soc. Rev. 38, 1380 (2009)

    Article  CAS  Google Scholar 

  98. N.I. Artemova, A.A. Krichko, YuI Petrov, Khim. Tverd. Topl. 1, 114 (1978)

    Google Scholar 

  99. A.A. Krichko, N.I. Artemova, A.V. Artemov, YuI Petrov, Kinet. Catal. 29, 134 (1988)

    Google Scholar 

  100. H.A. Smith, B.L. Stump, J. Am. Chem. Soc. 83, 2739 (1961)

    Article  CAS  Google Scholar 

  101. Sh Nishimura, Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis (Wiley, New York, 2001), pp. 414–482

    Google Scholar 

  102. S. Anderson, J.C. Jeffery, Y.-H. Liao, D.F. Mullica, E.L. Sappenfield, F.G.A. Stone, Organometallics 16, 958 (1997)

    Article  CAS  Google Scholar 

  103. S. Sentets, M.D.C.R. Martinez, L. Vendier, B. Donnadieu, V. Huc, N. Lugan, G. Lavigne, J. Am. Chem. Soc. 127, 14554 (2005)

    Article  CAS  Google Scholar 

  104. F. Schröder, D. Esken, M. Cokoja, M.W.E. van den Berg, O.I. Lebedev, G. van Tendeloo, B. Walaszek, G. Buntkowsky, H.-H. Limbach, B. Chaudret, J. Am. Chem. Soc. 130, 6119 (2008)

    Article  CAS  Google Scholar 

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Acknowledgments

This work was supported by the Russian Foundation for Basic Research, project No. 16-33-60101. Also, we thank Elena Skryleva (National University of Science and Technology “MISIS”, Moscow, Russia) for XPS facilities.

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Karakhanov, E., Maximov, A., Zolotukhina, A. et al. Thermo-responsive Ruthenium Dendrimer-based Catalysts for Hydrogenation of the Aromatic Compounds and Phenols. J Inorg Organomet Polym 26, 1264–1279 (2016). https://doi.org/10.1007/s10904-016-0399-2

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