Kurzaufsatz
Metalloenzymartige Zeolithe als Lewis-Säure-Katalysatoren für die C-C-Bindungsbildung
Dr. Stijn Van de Vyver,
Prof. Yuriy Román-Leshkov,
Dr. Stijn Van de Vyver
Department of Chemical Engineering, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139 (USA) http://www.romangroup.mit.edu
Search for more papers by this authorCorresponding Author
Prof. Yuriy Román-Leshkov
Department of Chemical Engineering, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139 (USA) http://www.romangroup.mit.edu
Department of Chemical Engineering, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139 (USA) http://www.romangroup.mit.eduSearch for more papers by this authorDr. Stijn Van de Vyver,
Prof. Yuriy Román-Leshkov,
Dr. Stijn Van de Vyver
Department of Chemical Engineering, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139 (USA) http://www.romangroup.mit.edu
Search for more papers by this authorCorresponding Author
Prof. Yuriy Román-Leshkov
Department of Chemical Engineering, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139 (USA) http://www.romangroup.mit.edu
Department of Chemical Engineering, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139 (USA) http://www.romangroup.mit.eduSearch for more papers by this authorAbstract
In den letzten Jahren wurde der Verwendung von metalloenzymartigen Zeolithen als Lewis-Säure-Katalysatoren für C-C-Kupplungen zunehmende Aufmerksamkeit geschenkt. Insbesondere die Beobachtung, dass hydrophobe Zeolithe mit isolierten Metallzentren im Gerüst direkte Aldolkondensationen ermöglichen, hat die Entwicklung von Katalyseverfahren für die Herstellung von Chemikalien ausgehend von aus Biomasse stammenden Verbindungen angestoßen. Die Entdeckung von neuen Diels-Alder-Cycloadditions-/Dehydratisierungswegen sowie experimentelle und rechnerische Untersuchungen von Lewis-Säure-katalysierten Carbonyl-En-Reaktionen haben die Entwicklung dieses schnell wachsenden Forschungsgebietes weiter vorangetrieben.
References
- 1M. J. Climent, A. Corma, S. Iborra in Zeolites and Catalysis, Wiley-VCH, Weinheim, 2010, S. 775–826.
10.1002/9783527630295.ch25 Google Scholar
- 2
- 2aP. A. Jacobs, M. Dusselier, B. F. Sels, Angew. Chem. Int. Ed. 2014, 53, 8621–8626; Angew. Chem. 2014, 126, 8765–8770;
- 2bP. N. R. Vennestrøm, C. M. Osmundsen, C. H. Christensen, E. Taarning, Angew. Chem. Int. Ed. 2011, 50, 10502–10509; Angew. Chem. 2011, 123, 10686–10694;
- 2cE. Taarning, C. M. Osmundsen, X. Yang, B. Voss, S. I. Andersen, C. H. Christensen, Energy Environ. Sci. 2011, 4, 793–804;
- 2dA. Corma, H. García, Chem. Rev. 2003, 103, 4307–4366.
- 3
- 3aH. Y. Luo, D. F. Consoli, W. R. Gunther, Y. Román-Leshkov, J. Catal. 2014, 320, 198;
- 3bP. Wolf, M. Valla, A. J. Rossini, A. Comas-Vives, F. Núñez-Zarur, B. Malaman, A. Lesage, L. Emsley, C. Copéret, I. Hermans, Angew. Chem. Int. Ed. 2014, 53, 10179–10183; Angew. Chem. 2014, 126, 10343–10347;
- 3cL. Bui, H. Luo, W. R. Gunther, Y. Román-Leshkov, Angew. Chem. Int. Ed. 2013, 52, 8022; Angew. Chem. 2013, 125, 8180;
- 3dR. Bermejo-Deval, R. Gounder, M. E. Davis, ACS Catal. 2012, 2, 2705–2713;
- 3eC. Hammond, S. Conrad, I. Hermans, Angew. Chem. Int. Ed. 2012, 51, 11736–11739; Angew. Chem. 2012, 124, 11906–11909;
- 3fY. Román-Leshkov, M. E. Davis, ACS Catal. 2011, 1, 1566–1580;
- 3gA. Corma, M. E. Domine, L. Nemeth, S. Valencia, J. Am. Chem. Soc. 2002, 124, 3194–3195.
- 4W. R. Gunther, V. K. Michaelis, M. A. Caporini, R. G. Griffin, Y. Román-Leshkov, J. Am. Chem. Soc. 2014, 136, 6219–6222.
- 5M. Moliner, Dalton Trans. 2014, 43, 4197–4208.
- 6P. Y. Dapsens, C. Mondelli, J. Perez-Ramirez, Chem. Soc. Rev. 2015, DOI: 10.1039/C5CS00028A.
- 7
- 7aJ. Lauwaert, E. G. Moschetta, P. Van Der Voort, J. W. Thybaut, C. W. Jones, G. B. Marin, J. Catal. 2015, 325, 19–25;
- 7bJ. Dijkmans, M. Dusselier, D. Gabriëls, K. Houthoofd, P. C. M. M. Magusin, S. Huang, Y. Pontikes, M. Trekels, A. Vantomme, L. Giebeler, S. Oswald, B. F. Sels, ACS Catal. 2014, 4, 928–940;
- 7cN. A. Brunelli, C. W. Jones, J. Catal. 2013, 308, 60–72;
- 7dN. A. Brunelli, K. Venkatasubbaiah, C. W. Jones, Chem. Mater. 2012, 24, 2433–2442;
- 7eE. L. Margelefsky, R. K. Zeidan, M. E. Davis, Chem. Soc. Rev. 2008, 37, 1118–1126.
- 8N. Kumagai, M. Shibasaki, Angew. Chem. Int. Ed. 2011, 50, 4760–4772; Angew. Chem. 2011, 123, 4856–4868.
- 9Y.-P. Li, M. Head-Gordon, A. T. Bell, ACS Catal. 2014, 4, 1537–1545.
- 10J. R. Cabrero-Antonino, A. Leyva-Pérez, A. Corma, Angew. Chem. Int. Ed. 2015, 54, 5658–5661; Angew. Chem. 2015, 127, 5750–5753.
- 11
- 11aM. Dusselier, P. Van Wouwe, S. De Smet, R. De Clercq, L. Verbelen, P. Van Puyvelde, F. E. Du Prez, B. F. Sels, ACS Catal. 2013, 3, 1786–1800;
- 11bM. S. Holm, Y. J. Pagan-Torres, S. Saravanamurugan, A. Riisager, J. A. Dumesic, E. Taarning, Green Chem. 2012, 14, 702–706.
- 12
- 12aS. Tolborg, I. Sádaba, C. M. Osmundsen, P. Fristrup, M. S. Holm, E. Taarning, ChemSusChem 2015, 8, 613–617;
- 12bM. Davis, Top Catal. 2015, 58, 405–409;
- 12cM. S. Holm, S. Saravanamurugan, E. Taarning, Science 2010, 328, 602–605.
- 13E. I. Gürbüz, J. M. R. Gallo, D. M. Alonso, S. G. Wettstein, W. Y. Lim, J. A. Dumesic, Angew. Chem. Int. Ed. 2013, 52, 1270–1274; Angew. Chem. 2013, 125, 1308–1312.
- 14S. Van de Vyver, C. Odermatt, K. Romero, T. Prasomsri, Y. Román-Leshkov, ACS Catal. 2015, 5, 972–977.
- 15Ausgewählte Beispiele:
- 15aH. Y. Kim, J.-Y. Li, K. Oh, Angew. Chem. Int. Ed. 2013, 52, 3736–3740; Angew. Chem. 2013, 125, 3824–3828;
- 15bS. J. Sauer, M. R. Garnsey, D. M. Coltart, J. Am. Chem. Soc. 2010, 132, 13997–13999;
- 15cM. C. Kohler, J. M. Yost, M. R. Garnsey, D. M. Coltart, Org. Lett. 2010, 12, 3376–3379.
- 16
- 16aS. Yamaguchi, T. Matsuo, K. Motokura, Y. Sakamoto, A. Miyaji, T. Baba, ChemSusChem 2015, 8, 853–860;
- 16bS. Yamaguchi, K. Motokura, Y. Sakamoto, A. Miyaji, T. Baba, Chem. Commun. 2014, 50, 4600–4602.
- 17S. Van de Vyver, J. Geboers, P. A. Jacobs, B. F. Sels, ChemCatChem 2011, 3, 82–94.
- 18J. D. Lewis, S. Van de Vyver, Y. Román-Leshkov, Angew. Chem. Int. Ed. 2015, 54, 9835–9838; Angew. Chem. 2015, 127, 9973–9976.
- 19E. Dumitriu, V. Hulea, I. Fechete, A. Auroux, J.-F. Lacaze, C. Guimon, Microporous Mesoporous Mater. 2001, 43, 341–359.
- 20E. Dumitriu, V. Hulea, C. Chelaru, C. Catrinescu, D. Tichit, R. Durand, Appl. Catal. A 1999, 178, 145–157.
- 21
- 21aE. Dumitriu, A. Azzouz, V. Hulea, D. Lutic, H. Kessler, Microporous Mater. 1997, 10, 1–12;
- 21bE. Dumitriu, N. Bilba, M. Lupascu, A. Azzouz, V. Hulea, G. Cirje, D. Nibou, J. Catal. 1994, 147, 133–139;
- 21cE. Dumitriu, V. Hulea, N. Bilba, G. Carja, A. Azzouz, J. Mol. Catal. 1993, 79, 175–185.
- 22V. Sushkevich, I. I. Ivanova, E. Taarning, Green Chem. 2015, 17, 2552–2559.
- 23E. V. Makshina, M. Dusselier, W. Janssens, J. Degreve, P. A. Jacobs, B. F. Sels, Chem. Soc. Rev. 2014, 43, 7917–7953.
- 24V. L. Sushkevich, I. I. Ivanova, V. V. Ordomsky, E. Taarning, ChemSusChem 2014, 7, 2527–2536.
- 25V. L. Sushkevich, I. I. Ivanova, E. Taarning, ChemCatChem 2013, 5, 2367–2373.
- 26V. V. Ordomsky, V. L. Sushkevich, I. I. Ivanova, J. Mol. Catal. A 2010, 333, 85–93.
- 27V. L. Sushkevich, I. I. Ivanova, S. Tolborg, E. Taarning, J. Catal. 2014, 316, 121–129.
- 28A. Corma, S. Iborra, M. Mifsud, M. Renz, J. Catal. 2005, 234, 96–100.
- 29T. J. Schwartz, S. M. Goodman, C. M. Osmundsen, E. Taarning, M. D. Mozuch, J. Gaskell, D. Cullen, P. J. Kersten, J. A. Dumesic, ACS Catal. 2013, 3, 2689–2693.
- 30
- 30aR. E. Patet, N. Nikbin, C. L. Williams, S. K. Green, C.-C. Chang, W. Fan, S. Caratzoulas, P. J. Dauenhauer, D. G. Vlachos, ACS Catal. 2015, 5, 2367–2375;
- 30bP. T. M. Do, J. R. McAtee, D. A. Watson, R. F. Lobo, ACS Catal. 2013, 3, 41–46;
- 30cC. L. Williams, C.-C. Chang, P. Do, N. Nikbin, S. Caratzoulas, D. G. Vlachos, R. F. Lobo, W. Fan, P. J. Dauenhauer, ACS Catal. 2012, 2, 935–939.
- 31N. Nikbin, P. T. Do, S. Caratzoulas, R. F. Lobo, P. J. Dauenhauer, D. G. Vlachos, J. Catal. 2013, 297, 35–43.
- 32
- 32aC.-C. Chang, S. K. Green, C. L. Williams, P. J. Dauenhauer, W. Fan, Green Chem. 2014, 16, 585–588;
- 32bY.-P. Li, M. Head-Gordon, A. T. Bell, J. Phys. Chem. C 2014, 118, 22090–22095.
- 33N. Nikbin, S. Feng, S. Caratzoulas, D. G. Vlachos, J. Phys. Chem. C 2014, 118, 24415–24424.
- 34
- 34aJ. J. Pacheco, M. E. Davis, Proc. Natl. Acad. Sci. USA 2014, 111, 8363–8367;
- 34bM. E. Davis, J. J. Pacheco, US20140364631A1, 2014.
- 35O. Casanova, S. Iborra, A. Corma, ChemSusChem 2009, 2, 1138–1144.
- 36
- 36aJ. D. Lewis, S. Van de Vyver, A. J. Crisci, W. R. Gunther, V. K. Michaelis, R. G. Griffin, Y. Román-Leshkov, ChemSusChem 2014, 7, 2255–2265;
- 36bJ. Jae, E. Mahmoud, R. F. Lobo, D. G. Vlachos, ChemCatChem 2014, 6, 508–513.
- 37M. A. Dam, E. De Jong, J. Van Haverden, A. Pukin, WO 2013048248A1, 2013.
- 38H. Fu, S. Xie, A. Fu, T. Ye, Comput. Theor. Chem. 2012, 982, 51–57.
- 39M. Boronat, P. Concepcion, A. Corma, M. T. Navarro, M. Renz, S. Valencia, Phys. Chem. Chem. Phys. 2009, 11, 2876–2884.
- 40
- 40aY. Nie, S. Jaenicke, G.-K. Chuah, Chem. Eur. J. 2009, 15, 1991–1999;
- 40bY. Nie, G.-K. Chuah, S. Jaenicke, Chem. Commun. 2006, 790–792;
- 40cZ. Yongzhong, N. Yuntong, S. Jaenicke, G.-K. Chuah, J. Catal. 2005, 229, 404–413;
- 40dA. Corma, M. Renz, Chem. Commun. 2004, 550–551.
- 41M. Boronat, A. Corma, M. Renz in Turning Points in Solid-State, Materials and Surf. Sci.: A Book in Celebration of the Life and Work of Sir John Meurig Thomas, The Royal Society of Chemistry, London, 2008, S. 639–650.
- 42
- 42aD. M. Do, S. Jaenicke, G.-K. Chuah, Catal. Sci. Technol. 2012, 2, 1417–1424;
- 42bE. A. Alarcón, L. Correa, C. Montes, A. L. Villa, Microporous Mesoporous Mater. 2010, 136, 59–67.
- 43A. Corma, M. Renz, Arkivoc 2007, 40–48.
- 44V. S. Marakatti, A. B. Halgeri, G. V. Shanbhag, Catal. Sci. Technol. 2014, 4, 4065.
- 45
- 45aS. Wannakao, P. Khongpracha, J. Limtrakul, J. Phys. Chem. A 2011, 115, 12486–12492;
- 45bW. Sangthong, M. Probst, J. Limtrakul, J. Mol. Struct. 2005, 748, 119–127.
- 46T. Okachi, M. Onaka, J. Am. Chem. Soc. 2004, 126, 2306–2307.
- 47R. Bermejo-Deval, M. Orazov, R. Gounder, S.-J. Hwang, M. E. Davis, ACS Catal. 2014, 4, 2288–2297.
- 48V. L. Sushkevich, D. Palagin, I. I. Ivanova, ACS Catal. 2015, 5, 4833–4836.
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