Metal-organic frameworks of the MIL-101 family as heterogeneous single-site catalysts

Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences

Volumn 468, Issue 2143, 2012, Pages 2017-2034

  Maksimchuk, Nataliya V ^a   Zalomaeva, Olga V ^a   Skobelev, Igor Y ^a   Kovalenko, Konstantin A ^b,c   Fedin, Vladimir P ^b,c   Kholdeeva, Oxana A ^a  

^a BORESKOV INSTITUTE OF CATALYSIS   (Russian Federation)

^b NIKOLAEV INSTITUTE OF INORGANIC CHEMISTRY   (Russian Federation)

^c NOVOSIBIRSK STATE UNIVERSITY   (Russian Federation)

Author keywords

Allylic oxidation; Carboxylation; Cyclohexane; Metal organic frameworks; MIL 101; Single site heterogeneous catalysts

Indexed keywords

CARBON DIOXIDE; CARBOXYLATION; CATALYSTS; CATALYTIC OXIDATION; CYCLOHEXANE; HYDROCARBONS; LEACHING; METALS;

ALLYLIC OXIDATION; CATALYTIC APPLICATIONS; COUPLING REACTION; HETEROGENEOUS CATALYST; LIQUID-PHASE PROCESS; MESOPOROUS; METAL LEACHING; METAL ORGANIC FRAMEWORK; MIL-101; SELECTIVE OXIDATION; SINGLE-SITE CATALYSTS;

CHROMIUM;

EID: 84862215157     PISSN: 13645021     EISSN: 14712946     Source Type: Journal    
DOI: 10.1098/rspa.2012.0072     Document Type: Conference Paper

References (47)

1. Anand, R., Hamdy, M. S., Gkourgkoulas, P., Maschmeyer, T., Jansen, J. C. & Hanefeld, U. 2006 Liquid phase oxidation of cyclohexane over transition metal incorporated amorphous 3D-mesoporous silicates M-TUD-1 (M=Ti, Fe, Co and Cr). Catal. Today 117, 279-283. (doi:10.1016/j.cattod.2006.05.031) (Pubitemid 44287317)
2. Aresta, M. (ed.) 2010 Carbon dioxide as chemical feedstock. Weincheim, Germany: Wiley-VCH.
3. Bauer, S., Serre, C., Devic, T., Horcajada, P., Marrot, J., Férey, G. & Stock, N. 2008 Highthroughput assisted rationalization of the formation of metal organic frameworks in the iron(III) aminoterephthalate solvothermal system. Inorg. Chem. 47, 7568-7576. (doi:10.1021/ ic800538r)
4. Blaser, H. U. & Studer, M. 1999 The role of catalysis for the clean production of fine chemicals. Appl. Catal. A 189, 191-204. (doi:10.1016/S0926- 860X(99)00276-8) (Pubitemid 129532987)
5. Cavani, F. & Alini, S. 2009 The synthesis of adipic acid: on the way to a more sustainable production. In Sustainable industrial processes (eds F. Cavani, G. Centi, S. Perathoner & F. Trifiro), pp. 367-426. New York, NY: Wiley-VCH.
6. Chen, J. D. & Sheldon, R. A. 1995 Selective oxidation of hydrocarbons with O2 over chromium aluminophosphate-5 molecular-sieve. J. Catal. 153, 1-8. (doi:10.1006/jcat.1995.1101)
7. Corma, A., García, H. & Llabrés i Xamena, F. X. 2010 Engineering metal organic frameworks for heterogeneous catalysis. Chem. Rev. 110, 4606-4655. (doi:10.1021/cr9003924)
8. Dapurkar, S. E., Kawanami, H., Komura, K., Yokoyama, T. & Ikushima, Y. 2008 Solvent-free allylic oxidation of cycloolefins over mesoporous CrMCM-41 molecular sieve catalyst at 1 atm dioxygen. Appl. Catal. A 346, 112-116. (doi:10.1016/j.apcata.2008.05.012)
9. Dhakshinamoorthy, A., Alvaro, M. & Garcia, H. 2011 Metal-organic frameworks as heterogeneous catalysts for oxidation reactions. Catal. Sci. Technol. 1, 856-867. (doi:10.1039/C1CY00068C)
10. Farrusseng, D. (ed.) 2011 Metal-organic frameworks: applications from catalysis to gas storage. Weinheim, Germany: Wiley-VCH.
11. Férey, G., Mellot-Draznieks, C., Serre, C., Millange, F., Dutour, J., Surblé, S. & Margiolaki, I. 2005 A chromium terephthalate-based solid with unusually large pore volumes and surface area. Science 309, 2040-2042. (doi:10.1126/science.1116275) (Pubitemid 41362318)
12. Fukuoka, S. et al. 2003 A novel non-phosgene polycarbonate production process using by-product CO2 as starting material. Green Chem. 5, 497-507. (doi:10.1039/B304963A) (Pubitemid 37443706)
13. Henschel, A., Gedrich, K., Kraehnert, R. & Kaskel, S. 2008 Catalytic properties of MIL-101. Chem. Commun. 2008, 4192-4194. (doi:10.1039/B718371B)
14. Hoffmann, F., Cornelius, M., Morell, J. & Fröba, M. 2006 Silica-based mesoporous organic- inorganic hybrid materials. Angew. Chem. Int. Ed. 45, 3216-3251. (doi:10.1002/anie.200503075) (Pubitemid 44098982)
15. Hong, D.-Y., Hwang, Y. K., Serre, C., Férey, G. & Chang, J.-S. 2009 Porous chromium terephthalate MIL-101 with coordinatively unsaturated sites: surface functionalization, encapsulation, sorption and catalysis. Adv. Funct. Mater. 19, 1537-1552. (doi:10.1002/adfm.200801130)
16. Hwang, Y. K., Hong, D.-Y., Chang, J.-S., Seo, H., Yoon, M., Kim, J., Jhung, S. H., Serre, C. & Férey, G. 2009 Selective sulfoxidation of aryl sulfides by coordinatively unsaturated metal centers in chromium carboxylate MIL-101. Appl. Catal. A 358, 249-253. (doi:10.1016/ j.apcata.2009.02.018)
17. Kholdeeva, O. A. 2006 Titanium-monosubstituted polyoxometalates: relation between homogeneous and heterogeneous Ti-single-site-based catalysis. Top. Catal. 40, 229-243. (doi:10.1007/s11244-006-0124-4)
18. Kholdeeva, O. A., Maksimchuk, N. V. & Maksimov, G. M. 2010 Polyoxometalate-based heterogeneous catalysts for liquid phase selective oxidations comparison of different strategies. Catal. Today 157, 107-113. (doi:10.1016/j.cattod.2009.12.016)
19. Kim, J., Bhattacharjee, S., Jeong, K.-E., Jeong, S.-Y. & Ahn, W.-S. 2009 Selective oxidation of tetralin over a chromium terephthalate metal organic framework, MIL-101. Chem. Commun. 2009, 3904-3906. (doi:10.1039/B902699A)
20. Kleist, W., Jutz, F., Maciejewski, M. & Baiker, A. 2009 Mixed-linker metal-organic frameworks as catalysts for the synthesis of propylene carbonate from propylene oxide and CO2. Eur. J. Inorg. Chem. 2009, 3552-3561. (doi:10.1002/ejic.200900509)
21. Lempers, H. E. B. & Sheldon, R. A. 1996 Allylic oxidation of olefins to the corresponding a, b-unsaturated ketones catalyzed by chromium aluminophosphate-5. Appl. Catal. A 143, 137-143. (doi:10.1016/0926-860X(96) 00076-2) (Pubitemid 126392415)
22. Maksimchuk, N. V., Kovalenko, K. A., Fedin, V. P. & Kholdeeva, O. A. 2010 Heterogeneous selective oxidation of alkenes to a,b-unsaturated ketones over coordination polymer MIL-101. Adv. Synth. Catal. 352, 2943-2948. (doi:10.1002/adsc.201000516)
23. Meléndez, J., North, M., Villuendas, P. & Young, C. 2011 One-component bimetallic aluminium(salen)-based catalysts for cyclic carbonate synthesis and their immobilization. Dalton Trans. 40, 3885-3902. (doi:10.1039/C0DT01196G)
24. Murphy, E. F., Mallat, T. & Baiker, A. 2000 Allylic oxofunctionalization of cyclic olefins with homogeneous and heterogeneous catalysts. Catal. Today 57, 115-126. (doi:10.1016/ S0920-5861(99)00314-4)
25. Musser, M. T. 2005 Cyclohexanol and cyclohexanone. In Ullmann's encyclopedia of industrial chemistry, electronic edn. Weinheim, Germany: Wiley-VCH Verlag.
26. North, M., Pasquale, R. & Young, C. 2010 Synthesis of cyclic carbonates from epoxides and CO2. Green Chem. 12, 1514-1539. (doi:10.1039/C0GC00065E)
27. Peppel, W. J. 1958 Preparation and properties of the alkylene carbonates. Ind. Eng. Chem. 50, 767-770. (doi:10.1021/ie50581a030)
28. Raja, R., Sankar, G. & Thomas, J. M. 1999 Powerful redox molecular sieve catalysts for the selective oxidation of cyclohexane in air. J. Am. Chem. Soc. 121, 11 926-11 927. (doi:10.1021/ ja9935052) (Pubitemid 30032789)
29. Ryan, O. B., Akporiaye, D. E., Holm, K. H. & Stöcker, M. 1997 Allylic oxidation of cyclohexene catalysed by metal exchanged zeolite Y. Stud. Surf. Sci. Catal. 108, 369-376. (doi:10.1016/ S0167-2991(97)80926-3) (Pubitemid 127819517)
30. Sakakura, T. & Kohno, K. 2009 The synthesis of organic carbonates from carbon dioxide. Chem. Commun. 11, 1312-1330. (doi:10.1039/B819997C)
31. Sakakura, T., Choi, J.-C. & Yasuda, H. 2007 Transformation of carbon dioxide. Chem. Rev. 107, 2365-2387. (doi:10.1021/cr068357u) (Pubitemid 47029097)
32. Sakthivel, A., Dapurkar, S. E. & Selvam, P. 2003 Allylic oxidation of cyclohexene over chromium containing mesoporous molecular sieves. Appl. Catal. A 246, 283-293. (doi:10.1016/ S0926-860x(03)00051-6)
33. Schuchardt, U., Cardoso, D., Sercheli, R., Pereira, R., de Cruz, R. S., Guerreiro, M. C., Mandelli, D., Spinacé, E. V. & Fires, E. L. 2001 Cyclohexane oxidation continues to be a challenge. Appl. Catal. A 211, 1-17. (doi:10.1016/S0926-860X(01)00472-0)
34. Selvaraj, M., Kandaswamy, M., Park, D. W. & Ha, C. S. 2010 Highly efficient and clean synthesis of verbenone over well ordered two-dimensional mesoporous chromium silicate catalysts. Catal. Today 158, 286-295. (doi:10.1016/j.cattod.2010.03.061)
35. Shaikh, A.-A. G. & Sivaram, S. 1996 Organic carbonates. Chem. Rev. 96, 951-976. (doi:10.1021/ cr950067i) (Pubitemid 126641474)
36. Sheldon, R. A. 2001 Allylic and benzylic oxidation. In Fine Chemicals through heterogeneous catalysis (eds R. A. Sheldon & H. van Bekkum), pp. 519-526. Weinheim, Germany: Wiley-VCH.
37. Sheldon, R. A., Wallau, M., Arends, I. W. C. E. & Schuchardt, U. 1998 Heterogeneous catalysts for liquid-phase oxidations: Philosophers' stones or Trojan horses? Acc. Chem. Res. 31, 485-493. (doi:10.1021/ar9700163) (Pubitemid 128474588)
38. Shylesh, S., Srilakshmi, Ch., Singh, A. P. & Anderson, B. G. 2007 One step synthesis of chromiumcontaining periodic mesoporous organosilicas and their catalytic activity in the oxidation of cyclohexane. Micropor. Mesopor. Mater. 99, 334-344. (doi:10.1016/j.micromeso.2006.09.029) (Pubitemid 46074466)
39. Song, J., Zhang, Z., Hu, S., Wu, T., Jiang, T. & Han, B. 2009 MOF-5/n-Bu4NBr: an efficient catalyst system for the synthesis of cyclic carbonates from epoxides and CO2 under mild conditions. Green Chem. 11, 1031-1036. (doi:10.1039/B902550B)
40. Srivastava, R., Srinivas, D. & Ratnasamy, P. 2003 Synthesis of polycarbonate precursors over titanosilicate molecular sieves. Catal. Lett. 91, 133-139. (doi:10.1023/B:CATL.0000006329. 37210.fd)
41. Srivastava, R., Srinivas, D. & Ratnasamy, P. 2005 CO2 activation and synthesis of cyclic carbonates and alkyl/aryl carbamates over adenine-modified Ti-SBA-15 solid catalysts. J. Catal. 233, 1-15. (doi:10.1016/j.jcat.2005.03.023)
42. Taylor-Pashow, K. M. L., Della Rocca, J., Xie, Z., Tran, S. & Lin W. 2009 Postsynthetic modifications of iron-carboxylate nanoscale metal-organic frameworks for imaging and drug delivery. J. Am. Chem. Soc. 131, 14 261-14 263. (doi:10.1021/ja906198y)
43. Thomas, J. M. 1988 Uniform heterogeneous catalysis-the role of solid-state chemistry in their development and design. Angew. Chem. Int. Ed. 27, 1673-1691. (doi:10.1002/anie.198816731)
44. Thomas, J. M. & Raja, R. 2006 The advantages and future potential of single-site heterogeneous catalysts. Top. Catal. 40, 3-17. (doi:10.1007/s11244- 006-0105-7)
45. Thomas, J. M. & Raja, R. 2010 Mono-, bi-and multifunctional single-sites: exploring the interface between heterogeneous and homogeneous catalysis. Top. Catal. 53, 848-858. (doi:10.1007/ s11244-010-9517-5)
46. Thomas, J. M., Raja, R. & Lewis, D. W. 2005 Single-site heterogeneous catalysts. Angew. Chem. Int. Ed. 44, 6456-6482. (doi:10.1002/anie.200462473) (Pubitemid 41502778)
47. Wight, A. P. & Davis, M. E. 2002 Design and preparation of organic-inorganic hybrid catalysts. Chem. Rev. 102, 3589-3614. (doi:10.1021/cr010334m) (Pubitemid 35350660)