Fabrication of titanosilicate pillared MFI zeolites with tailored catalytic activity

Abstract

Titanosilicate pillared MFI zeolite nanosheets were successfully synthesized by infiltrating the mixed tetraethyl orthosilicate (TEOS)/tetrabutyl orthotitanate (TBOT) solvent into the gallery space between adjacent MFI zeolite layers. The obtained zeolite catalysts were characterized using powder X-ray diffraction, N₂ adsorption/desorption isotherms, scanning electron microscopy, transmission electron microscopy, ultraviolet–visible spectroscopy, X-ray photoelectron spectroscopy, and Fourier-transform infrared spectroscopy techniques. The H₂O₂ oxidation of dibenzothiophene (DBT) was used to evaluate the catalytic performance of the obtained titanosilicate pillared MFI zeolites. The conversion of DBT and selectivity of dibenzothiophene sulfone (DBTS) were most affected by the textural properties of the zeolites. This was attributed to the DBT and DBTS molecules being larger than micropores of the MFI zeolites. The conversion of DBT and yield of DBTS could be systematically tailored by tuning the molar ratio of the TEOS/TBOT solvent. These results implied that a balance between the meso- and microporosity of zeolites and tetrahedrally coordinated Ti(IV) active sites of titanosilicate pillars can be achieved for the preparation of desired catalysts during the oxidation of bulk S compounds.

Graphical abstract

Keywords

MFI zeolite / catalysis / nanosheets / fabrication

References

[1] Bhutto A W, Abro R, Gao S, Abbas T, Chen X, Yu G. Oxidative desulfurization of fuel oils using ionic liquids: A review. Journal of the Taiwan Institute of Chemical Engineers, 2016, 62: 84–97

[2] Song C. An overview of new approaches to deep desulfurization for ultra-clean gasoline, diesel fuel and jet fuel. Catalysis Today, 2003, 86(1): 211–263

[3] Babich I V, Moulijn J A. Science and technology of novel processes for deep desulfurization of oil refinery streams: A review. Fuel, 2003, 82(6): 607–631

[4] Kowsari E. Ionic Liquids—New Aspects for the Future. Rijeka: InTech, 2013, 11–20

[5] García-Gutiérrez J L, Fuentes G A, Hernández-Terán M E, Murrieta F, Navarrete J, Jiménez-Cruz F. Ultra-deep oxidative desulfurization of diesel fuel with H₂O₂ catalyzed under mild conditions by polymolybdates supported on Al₂O₃. Applied Catalysis A, General, 2006, 305(1): 15–20

[6] Song C, Ma X. New design approaches to ultra-clean diesel fuels by deep desulfurization and deep dearomatization. Applied Catalysis B: Environmental, 2003, 41(1): 207–238

[7] Du Q, Guo Y, Duan H, Li H, Chen Y, Liu H. Synthesis of hierarchical TS-1 zeolite via a novel three-step crystallization method and its excellent catalytic performance in oxidative desulfurization. Fuel, 2017, 188: 232–238

[8] De Filippis P, Scarsella M, Verdone N. Oxidative desulfurization I: Peroxyformic acid oxidation of benzothiophene and dibenzothiophene. Industrial & Engineering Chemistry Research, 2010, 49(10): 4594–4600

[9] Song H, Li G, Wang X. In situ synthesis of Au/Ti-HMS and its catalytic performance in oxidation of bulky sulfur compounds using in situ generated H₂O₂ in the presence of H₂/O₂. Microporous and Mesoporous Materials, 2009, 120(3): 346–350

[10] Jiang B, Sun Z, Zhang L, Sun Y, Zhang H, Yang H. Synthesis of a hypercrosslinked, ionic, mesoporous polymer monolith and its application in deep oxidative desulfurization. Journal of Applied Polymer Science, 2018, 135(21): 46280

[11] Wang X, Li G, Wang W, Jin C, Chen Y. Synthesis, characterization and catalytic performance of hierarchical TS-1 with carbon template from sucrose carbonization. Microporous and Mesoporous Materials, 2011, 142(2): 494–502

[12] Chica A, Corma A, Dómine M E. Catalytic oxidative desulfurization (ODS) of diesel fuel on a continuous fixed-bed reactor. Journal of Catalysis, 2006, 242(2): 299–308

[13] Lv Q, Li G, Sun H. Synthesis of hierarchical TS-1 with convenient separation and the application for the oxidative desulfurization of bulky and small reactants. Fuel, 2014, 130: 70–75

[14] Wang W, Li G, Liu L, Chen Y. Synthesis and catalytic performance of hierarchical TS-1 directly using agricultural products sucrose as meso/macropores template. Microporous and Mesoporous Materials, 2013, 179: 165–171

[15] Jose N, Sengupta S, Basu J K. Optimization of oxidative desulfurization of thiophene using Cu/titanium silicate-1 by box-behnken design. Fuel, 2011, 90(2): 626–632

[16] Napanang T, Sooknoi T. Oxidative extraction of thiophene from n-dodecane over TS-1 in continuous process: A model for non-severe sulfur removal from liquid fuels. Catalysis Communications, 2009, 11(1): 1–6

[17] Sengupta A, Kamble P D, Basu J K, Sengupta S. Kinetic study and optimization of oxidative desulfurization of benzothiophene using mesoporous titanium silicate-1 catalyst. Industrial & Engineering Chemistry Research, 2012, 51(1): 147–157

[18] Přech J. Catalytic performance of advanced titanosilicate selective oxidation catalysts—a review. Catalysis Reviews, 2018, 60(1): 71–131

[19] Přech J, Vitvarová D, Lupínková L, Kubů M, Čejka J. Titanium impregnated borosilicate zeolites for epoxidation catalysis. Microporous and Mesoporous Materials, 2015, 212: 28–34

[20] Tsunoji N, Opanasenko M V, Kubů M, Čejka J, Nishida H, Hayakawa S, Ide Y, Sadakane M, Sano T. Highly active layered titanosilicate catalyst with high surface density of isolated titanium on the accessible interlayer surface. ChemCatChem, 2018, 10(12): 2536–2540

[21] Hulea V, Moreau P, Di Renzo F. Thioether oxidation by hydrogen peroxide using titanium-containing zeolites as catalysts. Journal of Molecular Catalysis A Chemical, 1996, 111(3): 325–332

[22] Corma A, Iglesias M, Sánchez F. Large pore Ti-zeolites and mesoporous Ti-silicalites as catalysts for selective oxidation of organic sulfides. Catalysis Letters, 1996, 39(3): 153–156

[23] Choi M, Cho H S, Srivastava R, Venkatesan C, Choi D H, Ryoo R. Amphiphilic organosilane-directed synthesis of crystalline zeolite with tunable mesoporosity. Nature Materials, 2006, 5(9): 718–723

[24] Choi M, Na K, Kim J, Sakamoto Y, Terasaki O, Ryoo R. Stable single-unit-cell nanosheets of zeolite MFI as active and long-lived catalysts. Nature, 2009, 461(7261): 246–249

[25] Fan W, Snyder M A, Kumar S, Lee P S, Yoo W C, McCormick A V, Lee Penn R, Stein A, Tsapatsis M. Hierarchical nanofabrication of microporous crystals with ordered mesoporosity. Nature Materials, 2008, 7(12): 984–991

[26] Wang H, Pinnavaia T J. MFI zeolite with small and uniform intracrystal mesopores. Angewandte Chemie International Edition, 2006, 45(45): 7603–7606

[27] Groen J C, Bach T, Ziese U, Paulaime-van Donk A M, de Jong K P, Moulijn J A, Pérez-Ramírez J. Creation of hollow zeolite architectures by controlled desilication of al-zoned ZSM-5 crystals. Journal of the American Chemical Society, 2005, 127(31): 10792–10793

[28] Liu B, Zheng L, Zhu Z, Li C, Xi H, Qian Y. Hierarchically structured Beta zeolites with intercrystal mesopores and the improved catalytic properties. Applied Catalysis A, General, 2014, 470: 412–419

[29] Du S, Chen X, Sun Q, Wang N, Jia M, Valtchev V, Yu J. A non-chemically selective top-down approach towards the preparation of hierarchical TS-1 zeolites with improved oxidative desulfurization catalytic performance. Chemical Communications, 2016, 52(17): 3580–3583

[30] Leng K, Sun Y, Zhang X, Yu M, Xu W. Ti-modified hierarchical mordenite as highly active catalyst for oxidative desulfurization of dibenzothiophene. Fuel, 2016, 174: 9–16

[31] Roth W J, Cejka J. Two-dimensional zeolites: Dream or reality? Catalysis Science & Technology, 2011, 1(1): 43–53

[32] Roth W J, Nachtigall P, Morris R E, Čejka J. Two-dimensional zeolites: Current status and perspectives. Chemical Reviews, 2014, 114(9): 4807–4837

[33] Kon Y, Yokoi T, Yoshioka M, Tanaka S, Uesaka Y, Mochizuki T, Sato K, Tatsumi T. Selective hydrogen peroxide oxidation of sulfides to sulfoxides or sulfones with MWW-type titanosilicate zeolite catalyst under organic solvent-free conditions. Tetrahedron, 2014, 70(41): 7584–7592

[34] Prech J, Morris R E, Cejka J. Selective oxidation of bulky organic sulphides over layered titanosilicate catalysts. Catalysis Science & Technology, 2016, 6(8): 2775–2786

[35] Liu B, Duan Q, Li C, Zhu Z, Xi H, Qian Y. Template synthesis of the hierarchically structured MFI zeolite with nanosheet frameworks and tailored structure. New Journal of Chemistry, 2014, 38(9): 4380–4387

[36] Xu D, Ma Y, Jing Z, Han L, Singh B, Feng J, Shen X, Cao F, Oleynikov P, Sun H, Terasaki O, Che S. p–p interaction of aromatic groups in amphiphilic molecules directing for single-crystalline mesostructured zeolite nanosheets. Nature Communications, 2014, 5(1): 4262

[37] Na K, Choi M, Park W, Sakamoto Y, Terasaki O, Ryoo R. Pillared MFI zeolite nanosheets of a single-unit-cell thickness. Journal of the American Chemical Society, 2010, 132(12): 4169–4177

[38] Emdadi L, Tran D T, Zhang J, Wu W, Song H, Gan Q, Liu D. Synthesis of titanosilicate pillared MFI zeolite as an efficient photocatalyst. RSC Advances, 2017, 7(6): 3249–3256

[39] Sing K S W. Reporting physisorption data for gas solid systems—with special reference to the determination of surface-area and porosity. Pure and Applied Chemistry, 1982, 54(11): 2201–2218

[40] Liu B, Li C, Ren Y, Tan Y, Xi H, Qian Y. Direct synthesis of mesoporous ZSM-5 zeolite by a dual-functional surfactant approach. Chemical Engineering Journal, 2012, 210(0): 96–102

[41] Jin F, Chang C, Yang C W, Lee J F, Jang L Y, Cheng S. New mesoporous titanosilicate MCM-36 material synthesized by pillaring layered ERB-1 precursor. Journal of Materials Chemistry. A, Materials for Energy and Sustainability, 2015, 3(16): 8715–8724

[42] Přech J, Eliášová P, Aldhayan D, Kubů M. Epoxidation of bulky organic molecules over pillared titanosilicates. Catalysis Today, 2015, 243: 134–140

[43] Zheng S, Heydenrych H R, Jentys A, Lercher J A. Influence of surface modification on the acid site distribution of HZSM-5. Journal of Physical Chemistry B, 2002, 106(37): 9552–9558

[44] Shetti V N, Manikandan P, Srinivas D, Ratnasamy P. Reactive oxygen species in epoxidation reactions over titanosilicate molecular sieves. Journal of Catalysis, 2003, 216(1): 461–467 doi:10.1016/S0021-9517(02)00119-7

[45] Camblor M A, Corma A, Perez-Pariente J. Infrared spectroscopic investigation of titanium in zeolites. A new assignment of the 960 cm^‒1 band. Journal of the Chemical Society. Chemical Communications, 1993, (6): 557–559

[46] Huang D G, Zhang X, Liu T W, Huang C, Chen B H, Luo C W, Ruckenstein E, Chao Z S. Synthesis of high-performanced titanium silicalite-1 zeolite at very low usage of tetrapropyl ammonium hydroxide. Industrial & Engineering Chemistry Research, 2013, 52(10): 3762–3772

[47] Lu H, Wang Y. Influence of seeds on the synthesis of TS-1 with inorganic materials. Reaction Kinetics and Catalysis Letters, 2006, 89(2): 219–227

[48] Tao Y, Kanoh H, Kaneko K. ZSM-5 monolith of uniform mesoporous channels. Journal of the American Chemical Society, 2003, 125(20): 6044–6045

[49] Liu B, Ren Y, Duan Q, Chen F, Xi H, Qian Y. Facile synthesis of mesoporous aluminosilicates constructed with crystalline microporous frameworks. Applied Surface Science, 2013, 279: 55–61

[50] Ji X, Xu L, Du X, Lu X, Lu W, Sun J, Wu P. Simple CTAB surfactant-assisted hierarchical lamellar MWW titanosilicate: A high-performance catalyst for selective oxidations involving bulky substrates. Catalysis Science & Technology, 2017, 7(13): 2874–2885

[51] Chandra D, Kishor Mal N, Mukherjee M, Bhaumik A. Titanium-rich highly ordered mesoporous silica synthesized by using a mixed surfactant system. Journal of Solid State Chemistry, 2006, 179(6): 1802–1807

[52] Mukhopadhayay S M, Garofalini S H. Surface studies of TiO₂ SiO₂ glasses by X-ray photoelectron spectroscopy. Journal of Non-Crystalline Solids, 1990, 126(3): 202–208

[53] Van de Voorde B, Hezinova M, Lannoeye J, Vandekerkhove A, Marszalek B, Gil B, Beurroies I, Nachtigall P, De Vos D. Adsorptive desulfurization with CPO-27/MOF-74: An experimental and computational investigation. Physical Chemistry Chemical Physics, 2015, 17(16): 10759–10766

[54] Ratnasamy P, Srinivas D, Knözinger H. Active sites and reactive intermediates in titanium silicate molecular sieves. Advances in Catalysis, 2004, 48: 1–169

[55] Zheng D, Zhu W, Xun S, Zhou M, Zhang M, Jiang W, Qin Y, Li H. Deep oxidative desulfurization of dibenzothiophene using low-temperature-mediated titanium dioxide catalyst in ionic liquids. Fuel, 2015, 159: 446–453

RIGHTS & PERMISSIONS

Higher Education Press and Springer-Verlag GmbH Germany, part of Springer Nature