journal article·2019-05

Immobilization of tungsten chelate complexes on functionalized mesoporous silica SBA-15 as heterogeneous catalysts for oxidation of cyclopentene

Manman Jin, Zhenmei Guo, Zhiguo Lv

Journal of Materials Science· Volume 54· Issue 9
Publisher page

Abstract

An efficient hybrid mesoporous heterogeneous catalyst system was synthesized via covalently grafting tungsten chelate complex W-N,N (N,N = (3-triethoxysilylpropyl) [3-(2-pyridyl)-1-pyrazolyl] acetamide, N,N-chelating ligand) in organic moieties (diphenyldichlorosilane, DPHS)-functionalized mesoporous silica SBA-15 or pure SBA-15. Characterization of synthesized materials via N2 sorption, XRD, TEM, UV–Vis DRS, 29Si MAS NMR, element analysis, and FT-IR indicated that W-N,N was successfully anchored and highly dispersed in the mesochannels of SBA-15 and the mesostructure of SBA-15 was maintained during the grafting course. The synthesized hybrid catalysts were highly active and authentically heterogeneous in triphasic oxidation reaction of cyclopentene (CPE) with H2O2. W,N-N immobilized on functionalized SBA-15 with DPHS moieties (W-N,N-DPHS-SBA-15) showed better catalytic properties (activity and stability) than its unmodified counterpart W-N,N-SBA-15 catalyst. Besides, possible catalytic reaction route for CPE oxidation with H2O2 over W-N,N-DPHS-SBA-15 catalyst was proposed. The amphiphilic mesochannels of W-N,N-DPHS-SBA-15 provided suitable accommodation for both hydrophilic H2O2 and hydrophobic CPE molecules and acted as nanoreactors for CPE/H2O2/solid triphase reaction.
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Research context

OpenAlex topics: Mesoporous Materials and Catalysis · Polyoxometalates: Synthesis and Applications · Covalent Organic Framework Applications

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References (52)

Show source-provided references
1. Ballantyne B, Jordan SL (2001) Toxicological, medical and industrial hygiene aspects of glutaraldehyde with particular reference to its biocidal use in cold sterilization procedures. J Appl Toxicol 21:131–15110.1002/jat.741 ↗
2. Dartiguenave MC, Bertrand MJ, Waldron KC (2004) Glutaraldehyde: behavior in aqueous solution, reaction with proteins, and application to enzyme crosslinking. Biotechniques 37:790–79610.2144/04375RV01 ↗
3. Thomas S, Russell AD (1974) Studies on the mechanism of the sporicidal action of glutaraldehyde. J Appl Bacteriol 37:83–9210.1111/j.1365-2672.1974.tb00417.x ↗
4. Sato K, Aoki M, Noyori R (1998) A “Green” route to adipic acid: direct oxidation of cyclohexenes with 30 percent hydrogen peroxide. Science 281:1646–164710.1126/science.281.5383.1646 ↗
5. Grigoropoulou G, Clark JH, Elings JA (2003) Recent developments on the epoxidation of alkenes using hydrogen peroxide as an oxidant. Green Chem 5:1–710.1039/b208925b ↗
6. Noyori R, Aoki M, Sato K (1977) Green oxidation with aqueous hydrogen peroxide. Chem Commun 34:1977–1986
7. Filip M, Todorova S, Shopska M, Ciobanu M, Papa F, Somacescu S, Munteanu C, Parvulescu V (2018) Effects of Ti loading on activity and redox behavior of metals in PtCeTi/KIT-6 catalysts for CH4 and CO oxidation. Catal Today 306:138–14410.1016/j.cattod.2017.02.013 ↗
8. Xun S, Jiang W, Guo T, He MQ, Ma RL, Zhang M, Zhu WS, Li HM (2019) Magnetic mesoporous nanospheres supported phosphomolybdate-based ionic liquid for aerobic oxidative desulfurization of fuel. J Colloid Interface Sci 534:239–24710.1016/j.jcis.2018.08.115 ↗
9. Singh R, Belgamwar R, Dhiman M, Polshettiwar V (2018) Dendritic fibrous nano-silica supported gold nanoparticles as an artificial enzyme. J Mater Chem B 6:1600–160410.1039/C8TB00310F ↗
10. Das P, Silva AR, Carvalho AP, Pires J, Freire C (2009) Organo-functionalized mesoporous supports for Jacobsen-type catalyst: laponite versus MCM-41. J Mater Sci 44:2865–2875. https://doi.org/10.1007/s10853-009-3379-x10.1007/s10853-009-3379-x ↗
11. Zhong NJ, Li Y, Cai CS, Gao YQ, Liu N, Liu GQ, Tan WY, Zeng YY (2018) Enhancing the catalytic performance of candida antarctica lipase B by immobilization onto the ionic liquids modified SBA-15. Eur J Lipid Sci Technol 120:1700357–170036310.1002/ejlt.201700357 ↗
12. Jin MM, Guo ZM, Ge XP, Lv ZG (2018) Tungsten-based organic mesoporous SBA-15 materials: characterization and catalytic properties in the oxidation of cyclopentene to glutaric acid with H2O2. React Kinet Mech Catal 125:1139–115710.1007/s11144-018-1486-x ↗
13. Peña ML, Dellarocca V, Rey F, Corma A, Coluccia S, Marchese L (2001) Elucidating the local environment of Ti(IV) active sites in Ti-MCM-48: a comparison between silylated and calcined catalysts. Microporous Mesoporous Mater 44–45:345–35610.1016/S1387-1811(01)00201-3 ↗
14. Yuan ZL, Chen S, Liu B (2017) Nitrogen-doped reduced graphene oxide-supported Mn3O4: an efficient heterogeneous catalyst for the oxidation of vanillyl alcohol to vanillin. J Mater Sci 52:164–172. https://doi.org/10.1007/s10853-016-0318-510.1007/s10853-016-0318-5 ↗
15. Lizama LY, Klimova TE (2009) SBA-15 modified with Al, Ti, or Zr as supports for highly active NiW catalysts for HDS. J Mater Sci 44:6617–6628. https://doi.org/10.1007/s10853-009-3613-610.1007/s10853-009-3613-6 ↗
16. Xun SH, Hou CZ, Li HP, He MQ, Ma RL, Zhang M, Zhu WS, Li HM (2018) Synthesis of WO3/mesoporous ZrO2 catalyst as a high-efficiency catalyst for catalytic oxidation of dibenzothiophene in diesel. J Mater Sci 53:15927–15938. https://doi.org/10.1007/s10853-018-2720-710.1007/s10853-018-2720-7 ↗
17. Lu G, Li XY, Qu ZP, Wang YX, Chen GH (2008) Selective oxidation of cyclopentene to glutaraldehyde over the WO3/SiO2 catalyst. Appl Surf Sci 255:3117–312010.1016/j.apsusc.2008.08.094 ↗
18. Yang XL, Gao RH, Dai WL, Fan KN (2008) Influence of tungsten precursors on the structure and catalytic properties of WO3/SBA-15 in the selective oxidation of cyclopentene to glutaraldehyde. J Phys Chem C 112:3819–382610.1021/jp710409g ↗
19. Yang XL, Dai WL, Chen H, Xu JH, Cao Y, Li HX, Fan KN (2005) Novel tungsten-containing mesoporous HMS material: its synthesis, characterization and catalytic application in the selective oxidation of cyclopentene to glutaraldehyde by aqueous H2O2. Appl Catal A Gen 283:1–810.1016/j.apcata.2004.12.029 ↗
20. Yang XL, Dai WL, Gao RH, Fan KN (2007) Characterization and catalytic behavior of highly active tungsten-doped SBA-15 catalyst in the synthesis of glutaraldehyde using an anhydrous approach. J Catal 249:278–28810.1016/j.jcat.2007.05.002 ↗
21. Jia MJ, Seifert A, Thiel WR (2003) Mesoporous MCM-41 materials modified with oxodiperoxo molybdenum complexes: efficient catalysts for the epoxidation of cyclooctene. Chem Mater 15:2174–218010.1021/cm021380l ↗
22. Tang JY, Wang L, Liu G, Liu Y, Hou YZ, Zhang WX, Jia MJ, Thiel WR (2009) Mesoporous SBA-15 materials modified with oxodiperoxo tungsten complexes as efficient catalysts for the epoxidation of olefins with hydrogen peroxide. J Mol Catal A: Chem 313:31–3710.1016/j.molcata.2009.07.018 ↗
23. Mimoun H, Roch ISD, Sajus L (1970) Epoxydation des olefines par les complexes peroxydiques covalents du molybdene-VI. Tetrahedron 26:37–5010.1016/0040-4020(70)85005-0 ↗
24. Dickman MH, Pope MT (1994) Peroxo and superoxo complexes of chromium, molybdenum, and tungsten. Chem Rev 94:569–58410.1021/cr00027a002 ↗
25. Zhao DY, Huo QS, Feng JL, Chmelka BF, Stucky GD (1998) Nonionic triblock and star diblock copolymer and oligomeric surfactant syntheses of highly ordered, hydrothermally stable, mesoporous silica structures. J Am Chem Soc 120:6024–603610.1021/ja974025i ↗
26. Cutrufello MG, Rombi E, Cannas C, Casu M, Virga A, Fiorilli S, Onida B, Ferino I (2009) Synthesis, characterization and catalytic activity of Au supported on functionalized SBA-15 for low temperature CO oxidation. J Mater Sci 44:6644–6653. https://doi.org/10.1007/s10853-009-3510-z10.1007/s10853-009-3510-z ↗
27. Orlov A, Zhai QZ, Klinowski J (2006) Photocatalytic properties of the SBA-15 mesoporous silica molecular sieve modified with titanium. J Mater Sci 41:2187–2193. https://doi.org/10.1007/s10853-006-7184-510.1007/s10853-006-7184-5 ↗
28. Huang ZD, Bensch W, Sigle W, Aken PAV, Kienle L, Vitoya T, Modrow H, Ressler T (2008) The modification of MoO3 nanoparticles supported on mesoporous SBA-15: characterization using X-ray scattering, N2 physisorption, transmission electron microscopy, high-angle annular darkfield technique, Raman and XAFS spectroscopy. J Mater Sci 43:244–253. https://doi.org/10.1007/s10853-007-2173-x10.1007/s10853-007-2173-x ↗
29. Szegedi Á, Popova M, Minchev C (2009) Catalytic activity of Co/MCM-41 and Co/SBA-15 materials in toluene oxidation. J Mater Sci 44:6710–6716. https://doi.org/10.1007/s10853-009-3600-y10.1007/s10853-009-3600-y ↗
30. Karimi B, Khorasani M (2013) Selectivity adjustment of SBA-15 based tungstate catalyst in oxidation of sulfides by incorporating a hydrophobic organic group inside the mesochannels. ACS Catal 3:1657–166410.1021/cs4003029 ↗
31. Li KG, Wang J, Zou YC, Song XJ, Gao HC, Zhu WC, Zhang WX, Yu JH, Jia MJ (2014) Surfactant-assisted sol–gel synthesis of zirconia supported phosphotungstates or Ti-substituted phosphotungstates for catalytic oxidation of cyclohexene. Appl Catal A Gen 482:84–9110.1016/j.apcata.2014.05.025 ↗
32. Pretsch E, Clerc T, Seibl J, Simon W (1983) Tables of spectral data for structure determination of organic compounds. Springer, Berlin10.1007/978-3-662-22455-7 ↗
33. Thu PTT, Thanh TT, Phi HN, Kim SJ, Vo V (2010) Adsorption of lead from water by thiol-functionalized SBA-15 silicas. J Mater Sci 45:2952–2957. https://doi.org/10.1007/s10853-010-4288-810.1007/s10853-010-4288-8 ↗
34. Shi XY, Han XY, Ma WJ, Wei JF, Li J, Zhang Q, Chen ZG (2011) Peroxotungstates immobilized on multilayer ionic liquid brushes-modified silica as an efficient and reusable catalyst for selective oxidation of sulfides with H2O2. J Mol Catal A: Chem 341:57–6210.1016/j.molcata.2011.03.024 ↗
35. Takei T, Houshito O, Yonesaki Y, Kumada N, Kinomura N (2007) Porous properties of silylated mesoporous silica and its hydrogen adsorption. J Solid State Chem 180:1180–118710.1016/j.jssc.2007.01.013 ↗
36. Zhu WS, Li HM, He XY, Zhang Q, Shu HM, Yan YS (2008) Synthesis of adipic acid catalyzed by surfactant-type peroxotungstates and peroxomolybdates. Catal Commun 9:551–55510.1016/j.catcom.2007.07.038 ↗
37. Li H, Xu Y, Yang HX, Zhang F, Li HX (2009) Ni-B amorphous alloy deposited on an aminopropyl and methyl co-functionalized SBA-15 as a highly active catalyst for chloronitrobenzene hydrogenation. J Mol Catal A: Chem 307:105–11410.1016/j.molcata.2009.03.015 ↗
38. Morales V, Villajos JA, García RA (2013) Simultaneous synthesis of modified Binol-periodic mesoporous organosilica SBA-15 type material. Application as catalysts in asymmetric sulfoxidation reactions. J Mater Sci 48:5990–6000. https://doi.org/10.1007/s10853-013-7395-510.1007/s10853-013-7395-5 ↗
39. Pursch M, Sander LC, Albert K (1996) Chain order and mobility of high-density C18 phases by solid-state NMR spectroscopy and liquid chromatography. Anal Chem 68:4107–411310.1021/ac9606113 ↗
40. Zhao XS, Lu GQ (1998) Modification of MCM-41 by surface silylation with trimethylchlorosilane and adsorption study. J Phys Chem B 102(1998):1556–156110.1021/jp972788m ↗
41. Farahani MM, Modarres M (2016) Wells-Dawson heteropoly acid immobilized inside the nanocages of SBA-16 with ship-in-a-bottle method: a new recoverable catalyst for the epoxidation of olefins. J Mol Catal A: Chem 417:81–8810.1016/j.molcata.2016.03.016 ↗
42. Zhao XS, Lu GQ, Whittaker AK, Millar GJ, Zhu HY (1997) Comprehensive study of surface chemistry of MCM-41 using 29Si CP/MAS NMR, FTIR, Pyridine-TPD, and TGA. J Phys Chem B 101:6525–653110.1021/jp971366+ ↗
43. Bordoloi A, Sahoo S, Lefebvre F, Halligudi SB (2008) Heteropoly acid-based supported ionic liquid-phase catalyst for the selective oxidation of alcohols. J Catal 259:232–23910.1016/j.jcat.2008.08.010 ↗
44. Wang L, Shylesh S, Dehe D, Philippi T, Dörr G, Seifert A, Zhou Z, Hartmann M, Taylor RNK, Jia MJ, Ernat S, Thiel WR (2012) Covalent immobilization of imidazolium cations inside a silica support: palladium-catalyzed olefin hydrogenation. Chemcatchem 4:395–40010.1002/cctc.201100329 ↗
45. Tan R, Liu C, Feng ND, Xiao J, Zheng WG, Zheng AM, Yin DH (2012) Phosphotungstic acid loaded on hydrophilic ionic liquid modified SBA-15 for selective oxidation of alcohols with aqueous H2O2. Microporous Mesoporous Mater 158:77–8710.1016/j.micromeso.2012.03.023 ↗
46. Zhang RY, Ding W, Tu B, Zhao DY (2007) Mesoporous silica: an efficient nanoreactor for liquid–liquid biphase reactions. Chem Mater 19:4379–438110.1021/cm071718h ↗
47. Hulea V, Dumitriu E, Patcas F, Ropot R, Graffin P, Moreau P (1998) Cyclopentene oxidation with H2O2 over Ti-containing zeolites. Appl Catal A Gen 170:169–17510.1016/S0926-860X(98)00047-7 ↗
48. Clerici MG, Ingallina P (1993) Epoxidation of lower olefins with hydrogen peroxide and titanium silicalite. J Catal 140:71–8310.1006/jcat.1993.1069 ↗
49. Jin RH, Xia X, Dai WL, Deng JF, Li HX (1999) An effective heterogeneous WO3/TiO2–SiO2 catalyst for selective oxidation of cyclopentene to glutaraldehyde by H2O2. Catal Lett 62:201–20710.1023/A:1019094905328 ↗
50. Chibani S, Michel C, Delbecq F, Pinel C, Besson M (2013) On the key role of hydroxyl groups in platinum-catalysed alcohol oxidation in aqueous medium. Catal Sci Technol 3:339–35010.1039/C2CY20363D ↗
51. Deng JF, Xu XH, Chen HY, Jiang AR (1992) A new process for preparing dialdehydes by catalytic oxidation of cyclic olefins with aqueous hydrogen peroxide. Tetrahedron 48:3503–351410.1016/S0040-4020(01)88489-1 ↗
52. Jin RH, Li HX, Deng JF (2001) Selective oxidation of cyclopentene to glutaraldehyde by H2O2 over the WO3/SiO2 Catalyst. J Catal 203:75–8110.1006/jcat.2001.3319 ↗