Abstract
Three dimensional (3D) cubic cage like Im3m mesoporous SBA-16 was synthesized by one pot hydrothermal method using Pluronic F127 as structure directing agent and Tetraethylorthosilicate as silica precursor. Different weight percentages (1 wt%, 3 wt% and 5 wt%) of manganese nitrate tetrahydrate were homogeneously mixed with the same weight percentages of ammonium tungsten oxide hydrate respectively and dispersed on SBA-16 by incipient wet impregnation method. Structural identification and the particle arrangement for as-synthesized SBA-16 materials were analyzed using low and high angle X-ray diffraction. Surface area, pore-diameter, pore volume and pore size distribution were observed using the N2 adsorption isotherm technique with H2 hysteresis loop. The topography of the catalyst was characterized by TEM. The chemical valence state and elemental composition were characterized by high-resolution XPS respectively. The thermal stability of the catalyst was characterized by Thermogravimetric analysis. The synthesized materials MnWO4/SBA-16 were tested for epoxidation of styrene with environmentally benign TBHP as an oxidant. Various parametric investigations were performed and reported. From the above investigation, it is inferred that the major product of styrene oxide was obtained with maximum selectivity of about 75% using MnWO4 (3 wt%)/SBA-16.
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References
V. Chaudhary, Sweta, Synthesis and catalytic activity of SBA-15 supported catalysts for styrene oxidation. Chin. J. Chem. Eng. 26(6), 1300–1306 (2018). https://doi.org/10.1016/j.cjche.2018.01.025
S. Li, H. Zhou, C. Jin, N. Feng, F. Liu, F. Deng, J. Fan, Formation of subnanometer Zr-WOx clusters within mesoporous W-Zr mixed oxides as strong solid acid catalysts for friedel-crafts alkylation. J. Phys. Chem. C 118(12), 6283–6290 (2014). https://doi.org/10.1021/jp4119088
F. Li, X. Xu, J. Huo, W. Wang, A simple synthesis of MnWO4 nanoparticles as a novel energy storage material. Mater. Chem. Phys. 167, 22–27 (2015). https://doi.org/10.1016/j.matchemphys.2015.06.029
T. Li, C. Yang, X. Rao, F. Xiao, J. Wang, X. Su, Synthesis of magnetically recyclable Fe3O4@NiO nanostructures for styrene epoxidation and adsorption application. Ceram. Int. 41(2, Part A), 2214–2220 (2015). https://doi.org/10.1016/j.ceramint.2014.10.022
S. Lwin, I.E. Wachs, Olefin metathesis by supported metal oxide catalysts. ACS Catal. 4(8), 2505–2520 (2014). https://doi.org/10.1021/cs500528h
Q. Meng, H. Li, H. Li, Self-assembly of mesoporous ruthenium−boron amorphous alloy catalysts with enhanced activity in maltose hydrogenation to maltitol. J. Phys. Chem. C 112(30), 11448–11453 (2008). https://doi.org/10.1021/jp802916t
N. Musselwhite, K. Na, K. Sabyrov, S. Alayoglu, G.A. Somorjai, Mesoporous aluminosilicate catalysts for the selective isomerization of n-hexane: the roles of surface acidity and platinum metal. J. Am. Chem. Soc. 137(32), 10231–10237 (2015). https://doi.org/10.1021/jacs.5b04808
A. Palani, A. Pandurangan, Esterification of acetic acid over mesoporous Al-MCM-41 molecular sieves. J. Mol. Catal. A: Chem. 226(1), 129–134 (2005). https://doi.org/10.1016/j.molcata.2004.09.017
S. Pichaikaran, P. Arumugam, Vapour phase hydrodeoxygenation of anisole over ruthenium and nickel supported mesoporous aluminosilicate. Green Chem. 18(9), 2888–2899 (2016). https://doi.org/10.1039/c5gc01854d
R. Savidha, A. Pandurangan, Vapour phase isopropylation of phenol over zinc- and iron-containing Al-MCM-41 molecular sieves. Appl. Catal. A 262(1), 1–11 (2004). https://doi.org/10.1016/j.apcata.2003.08.018
S. Vetrivel, A. Pandurangan, Co and Mn impregnated MCM-41: their applications to vapour phase oxidation of isopropylbenzene. J. Mol. Catal. A: Chem. 227(1), 269–278 (2005). https://doi.org/10.1016/j.molcata.2004.10.036
Z. Wang, Y. Jiang, Y. Zhang, J. Shi, C. Stampfl, M. Hunger, J. Huang, Identification of vicinal silanols and promotion of their Formation on MCM-41 via ultrasonic assisted one-step room-temperature synthesis for beckmann rearrangement. Ind. Eng. Chem. Res. 57(16), 5550–5557 (2018). https://doi.org/10.1021/acs.iecr.8b00274
K. Patel, V. Brahmkhatri, A. Patel, Manganese (III) salen supported onto hydrous zirconia: synthesis, characterization, and solvent free aerobic oxidation of styrene. Synth. React. Inorg., Met.-Org., Nano-Met. Chem. 45(4), 539–545 (2015). https://doi.org/10.1080/15533174.2013.841220
H. Cui, Y. Zhang, Z. Qiu, L. Zhao, Y. Zhu, Synthesis and characterization of cobalt-substituted SBA-15 and its high activity in epoxidation of styrene with molecular oxygen. Appl. Catal. B 101(1), 45–53 (2010). https://doi.org/10.1016/j.apcatb.2010.09.003
M. Fadhli, I. Khedher, J.M. Fraile, Modified Ti/MCM-41 catalysts for enantioselective epoxidation of styrene. J. Mol. Catal. A: Chem. 420, 282–289 (2016). https://doi.org/10.1016/j.molcata.2016.05.001
G. Imran, V.V. Srinivasan, R. Maheswari, A. Ramanathan, B. Subramaniam, Unique characteristics of MnOx-incorporated mesoporous silicate, Mn-FDU-5, prepared via evaporation induced self assembly. J. Porous Mater. 23(1), 57–65 (2016). https://doi.org/10.1007/s10934-015-0055-1
B. Li, X. Luo, J. Huang, X. Wang, Z. Liang, One-pot synthesis of ordered mesoporous Cu-KIT-6 and its improved catalytic behavior for the epoxidation of styrene: effects of the pH value of the initial gel. Chin. J. Catal. 38(3), 518–528 (2017). https://doi.org/10.1016/S1872-2067(17)62767-0
S. Mandal, A. SinhaMahapatra, B. Rakesh, R. Kumar, A. Panda, B. Chowdhury, Synthesis, characterization of Ga-TUD-1 catalyst and its activity towards styrene epoxidation reaction. Catal. Commun. 12(8), 734–738 (2011). https://doi.org/10.1016/j.catcom.2011.01.004
S. Wongkasemjit, S. Tamuang, W. Tanglumlert, T. Imae, Synthesis of Mo-SBA-1 catalyst via sol–gel process and its activity. Mater. Chem. Phys. 117(1), 301–306 (2009). https://doi.org/10.1016/j.matchemphys.2009.06.004
M. Selvaraj, P.K. Sinha, K. Lee, I. Ahn, A. Pandurangan, T.G. Lee, Synthesis and characterization of Mn–MCM-41and Zr–Mn-MCM-41. Microporous Mesoporous Mater. 78(2), 139–149 (2005). https://doi.org/10.1016/j.micromeso.2004.10.004
A. Ramanathan, B. Subramaniam, D. Badloe, U. Hanefeld, R. Maheswari, Direct incorporation of tungsten into ultra-large-pore three-dimensional mesoporous silicate framework: W-KIT-6. J. Porous Mater. 19(6), 961–968 (2012). https://doi.org/10.1007/s10934-011-9553-y
Q. Zhang, Y. Wang, S. Itsuki, T. Shishido, K. Takehira, Manganese-containing MCM-41 for epoxidation of styrene and stilbene. J. Mol. Catal. A: Chem. 188(1), 189–200 (2002). https://doi.org/10.1016/S1381-1169(02)00323-0
L.H. Hoang, P.V. Hanh, N.D. Phu, X.-B. Chen, W.C. Chou, Synthesis and characterization of MnWO4 nanoparticles encapsulated in mesoporous silica SBA-15 by fast microwave-assisted method. J. Phys. Chem. Solids 77, 122–125 (2015). https://doi.org/10.1016/j.jpcs.2014.10.013
X. Li, T. Lunkenbein, J. Kröhnert, V. Pfeifer, F. Girgsdies, F. Rosowski, A. Trunschke, Hydrothermal synthesis of bi-functional nanostructured manganese tungstate catalysts for selective oxidation. Faraday Discuss. 188, 99–113 (2016). https://doi.org/10.1039/c5fd00191a
D.D. Mal, S. Khilari, D. Pradhan, Efficient and selective oxidation of toluene to benzaldehyde on manganese tungstate nanobars: a noble metal-free approach. Green Chem. 20(10), 2279–2289 (2018). https://doi.org/10.1039/c8gc00123e
A. Wang, X.Y. Liu, C.-Y. Mou, T. Zhang, Understanding the synergistic effects of gold bimetallic catalysts. J. Catal. 308, 258–271 (2013). https://doi.org/10.1016/j.jcat.2013.08.023
S. Kavian, S.N. Azizi, S. Ghasemi, Novel bimetallic nanoporous Pd-Cu-SBA-16/CPE as a highly sensitive sensor for determination of formaldehyde. J. Electroanal. Chem. 799, 308–314 (2017). https://doi.org/10.1016/j.jelechem.2017.06.006
G. Vijayakumar, A. Pandurangan, Up-gradation of α-tetralone to jet-fuel range hydrocarbons by vapour phase hydrodeoxygenation over PdNi/SBA-16 catalysts. Energy 140, 1158–1172 (2017). https://doi.org/10.1016/j.energy.2017.09.038
G.F. Andrade, D.C.F. Soares, R.G. dos Santos, E.M.B. Sousa, Mesoporous silica SBA-16 nanoparticles: synthesis, physicochemical characterization, release profile, and in vitro cytocompatibility studies. Microporous Mesoporous Mater. 168, 102–110 (2013). https://doi.org/10.1016/j.micromeso.2012.09.034
S. Zhang, S. Muratsugu, N. Ishiguro, M. Tada, Ceria-doped Ni/SBA-16 catalysts for dry reforming of methane. ACS Catal. 3(8), 1855–1864 (2013). https://doi.org/10.1021/cs400159w
N. Anbazhagan, G. Imran, A. Qurashi, A. Pandurangan, S. Manimaran, Confinement of Mn3+ redox sites in Mn-KIT-6 and its catalytic activity for styrene epoxidation. Microporous Mesoporous Mater. 247, 190–197 (2017)
J.C. Amezcua, L. Lizama, C. Salcedo, I. Puente, J.M. Domínguez, T. Klimova, NiMo catalysts supported on titania-modified SBA-16 for 4,6-dimethyldibenzothiophene hydrodesulfurization. Catal. Today 107–108, 578–588 (2005). https://doi.org/10.1016/j.cattod.2005.07.018
E. Poonia, S. Duhan, K. Kumar, A. Kumar, S. Jakhar, V.K. Tomer, One pot hydrothermal synthesis of ordered mesoporous SnO2/SBA-16 nanocomposites. J. Porous Mater. 26(2), 553–560 (2019)
S. Saranya, S. Senthilkumar, K.V. Sankar, R.K. Selvan, Synthesis of MnWO4 nanorods and its electrical and electrochemical properties. J. Electroceram. 28(4), 220–225 (2012)
D. Carta, M.F. Casula, S. Bullita, A. Falqui, A. Corrias, Iron–cobalt nanocrystalline alloy supported on a cubic mesostructured silica matrix: FeCo/SBA-16 porous nanocomposites. J. Nanopart. Res. 13(8), 3489–3501 (2011). https://doi.org/10.1007/s11051-011-0270-x
A. Feliczak-Guzik, P. Szczyglewska, I. Nowak, The effect of metal (Nb, Ru, Pd, Pt) supported on SBA-16 on the hydrodeoxygenation reaction of phenol. Catal. Today 325, 61–67 (2019)
M.O. Alonso-Pérez, B. Pawelec, T.A. Zepeda, G. Alonso-Núñez, R. Nava, R.M. Navarro, R. Huirache-Acuña, Effect of the titanium incorporation method on the morphology and HDS activity of supported ternary Ni–Mo–W/SBA-16 catalysts. Microporous Mesoporous Mater. 312, 110779 (2021). https://doi.org/10.1016/j.micromeso.2020.110779
A.A. Hussain, S. Nazir, R. Irshad, K. Tahir, M. Raza, Z.U.H. Khan, A.U. Khan, Synthesis of functionalized mesoporous Ni-SBA-16 decorated with MgO nanoparticles for Cr (VI) adsorption and an effective catalyst for hydrodechlorination of chlorobenzene. Mater. Res. Bull. 133, 111059 (2021)
J. Liu, R. Meng, J. Li, P. Jian, L. Wang, R. Jian, Achieving high-performance for catalytic epoxidation of styrene with uniform magnetically separable CoFe2O4 nanoparticles. Appl. Catal. B 254, 214–222 (2019)
J. Liu, R. Meng, H. Wang, P. Jian, Boosting styrene epoxidation via CoMn2O4 microspheres with unique porous yolk-shell architecture and synergistic intermetallic interaction. J. Colloid Interface Sci. 579, 221–232 (2020)
Y. Shi, L. Chen, Q. Hu, G. Ji, Y. Lu, X. Hu, W. Huang, Co supported on interparticle porosity dominated hierarchical porous TS-1 as highly efficient heterogeneous catalyst for epoxidation of styrene. Chem. Phys. Lett. 762, 138116 (2021)
N.T. Dat, T.T.N. Mai, K.-S. Lin, N.T.M. Thu, N.T. Thao, Reactivity of styrene with tert-butyl hydroperoxide over cu-based double hydroxide catalysts. Mol. Catal. 500, 111337 (2021)
M. Abboud, N. Al-Zaqri, T. Sahlabji, M. Eissa, A.T. Mubarak, R. Bel-Hadj-Tahar, M.S. Hamdy, Instant and quantitative epoxidation of styrene under ambient conditions over a nickel (ii) dibenzotetramethyltetraaza [14] annulene complex immobilized on amino-functionalized SBA-15. RSC Adv. 10(58), 35407–35418 (2020)
T. Sahlabji, M. Abboud, R. Bel-Hadj-Tahar, M.S. Hamdy, Spontaneous epoxidation of styrene catalyzed by flower-like NiO nanoparticles under ambient conditions. J. Nanopart. Res. 22(12), 1–10 (2020)
J. Liu, F. Wang, S. Qi, Z. Gu, G. Wu, Highly selective epoxidation of styrene over gold–silica catalysts via one-pot synthesis: synthesis, characterization, and catalytic application. New J. Chem. 37(3), 769–774 (2013)
J. Liu, F. Wang, T. Xu, Z. Gu, Styrene Epoxidation over Carbon Nanotube-Supported Gold Catalysts. Catal. Lett. 134(1), 51–55 (2010). https://doi.org/10.1007/s10562-009-0230-6
B. Tang, W. Dai, X. Sun, N. Guan, L. Li, M. Hunger, A procedure for the preparation of Ti-Beta zeolites for catalytic epoxidation with hydrogen peroxide. Green Chem. 16(4), 2281–2291 (2014). https://doi.org/10.1039/c3gc42534g
B. Li, M. Wang, L. Wu, X. Wang, Efficient epoxidation of styrene using tert-butyl hydroperoxide promoted by M0. 5Cu0. 5Co2Ox (M= Ca, Ni, and Cr) ternary catalysts. Ind. Eng. Chem. Res. 59(23), 10778–10789 (2020)
W. Zheng, R. Tan, L. Zhao, Y. Chen, C. Xiong, D. Yin, Mn2+/graphene oxide nanocomposite efficiently catalyzes the epoxidation of alkenes with H2O2. RSC Adv. 4(23), 11732–11739 (2014). https://doi.org/10.1039/c3ra47183g
Acknowledgements
One of the authors, S. Manimaran acknowledges the Anna Centenary Research Fellowship (ACRF) funded by Anna University, Chennai for the financial support to carry out this work. The authors are thankful to the DST-FIST-sponsored Department of Chemistry, Anna University, for providing the laboratory and instrumentation facilities.
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Manimaran, S., Subramanian, K., Tschentscher, R. et al. Epoxidation of alkene using bi-functional metal oxide supported SBA-16 catalyst. J Porous Mater 29, 357–369 (2022). https://doi.org/10.1007/s10934-021-01170-5
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DOI: https://doi.org/10.1007/s10934-021-01170-5