Abstract
A new series of cobalt/zinc-grafted mesoporous silica nanoparticles (CZ-MSN) catalysts were synthesized and characterized using FTIR, SEM, TEM, XRD and nitrogen adsorption-desorption. The molar ratio of Si/Zn was 10 and the amounts of cobalt atom were 1, 3, 5 and 7 wt% (denoted as CZM-X). The nitrogen adsorption/desorption results showed that the surface area increased from 322 in CZM-7 to 408 m2g−1 in CZM-1. The catalytic activity was investigated for the oxidation reaction by cyclohexanone oxime synthesis from cyclohexanimine using ozone gas flow under UV light at room temperature for 20 min. The results showed that the oxidation of cyclohexanimine to cyclohexanone oxime was 98% over CZM-1 and its selectivity was 97%. The catalytic activity decreased with increasing the cobalt atoms as the order of CZM-1 > CZM-3 > CZM-5 > CZM-7 > Zn-MSN > MSN. The significant advantages of using CZM-1 including high conversion and selectivity, low reaction temperature, and short reaction time. This study introduces a new pathway for oxime synthesis with excellent performance.
Similar content being viewed by others
References
Sletten EM, Bertozzi CR (2009) Bioorthogonal chemistry: fishing for selectivity in a sea of functionality. Angew Chem Int Ed Engl 48:6974–6998
Tang W, Becker ML (2014) “Click” reactions: a versatile toolbox for the synthesis of peptide-conjugates. Chem Soc Rev 43:7013–7039
Kolme DK, Kool ET (2017) Oximes and Hydrazones in bioconjugation: mechanism and catalysis. Chem Rev 117:10358–10376
Yavari I, Ramazami A (1997) Triphenylphosphine Catalyzed Stereoselective Synthesis of O-Vinyloximes. Synth Commun 27(8):1449–1454
Tanase S, Hierso JC, Bouwman E (2003) New insights on the anti-skinning effect of methyl ethyl ketoxime in alkyd paints. New J Chem 27:854–859
Cho H (2014) Rearrangement of oximes and hydroxylamines with aluminium reductants. Tetrahedron 70(22):3527–3544
Narang R, Narasimhan B, Sharma BA (2012) Review on biological activities and chemical synthesis of hydrazide derivatives. Curr Med Chem 19:569–612
Ulrich S, Boturyn D, Marra A, Renaudet O (2014) Oxime ligation: a Chemoselective click-type reaction for accessing multifunctional biomolecular constructs. Chem Eur J 20:34–41
Agten SM, Dawson PE, Hackeng TM (2016) Oxime conjugation in protein chemistry: from carbonyl incorporation to nucleophilic catalysis. J Pept Sci 22:271–279
Chen R, Mao H, Zhang X, Xing W, Fan YA (2014) Dual-membrane airlift reactor for cyclohexanone ammoximation over titanium silicalite-1. Ind Eng Chem Res 53(15):6372–6379
Li L, Liu B, Wu Z, Yuan X, Luo H (2015) Preparation of Keggin-type mono-lacunary phosphotungstic-ammonium salt and its catalytic performance in ammoximation of cyclohexanone. Chem Eng J 280:670–676
Li Z, Yang Q, Qi X, Xu Y, Zhang D, Wang Y, Zhao X (2015) A novel hydroxylamine ionic liquid salt resulting from the stabilization of NH2OH by a SO3Hfunctionalized ionic liquid. Chem Commun 51(10):1930–1932
Robertson G. M, Katritzky G. R, Meth-Cohn O, Rees C. W (1995) Comprehensive organic functional group transformation 2nd edition Elsevier Oxford 425–441
Cavani F, Ballarini N, Luciani S (2009) Catalysis for society: towards improved process efficiency in catalytic selective oxidations. Top Catal 52:935–947
Freakley SJ, Lewis RJ, Morgan DJ, Edwards JK, Hutchings GJ (2015) Direct synthesis of hydrogen peroxide using au-Pd supported and ion-exchanged heteropolyacids precipitated with various metal ions. Catal Today 248:10–17
Ramazani A, Rouhani M, Joo SW (2018) Silica Nanoparticles from Rice husk ash: a green catalyst for the one-pot three component synthesis of Benzo [B] furan derivatives. Adv Mater Res 875-877:202–207
Ahankar H, Ramazani A, Fattahi N, Slepokura K, Lis T, Azimzadeh Asiabi P, Kinzhybalo V, Hanifehpour Y, Joo SW (2018) Tetramethylguanidine-functionalized silica-coated iron oxide magnetic nanoparticles catalyzed one-pot three-component synthesis of furanone derivatives. J. Chem. Sci. 130:166
Fattahi N, Ramazani A, Ahankar H, Asiabi PA, Kinzhybalo V (2019) Tetramethylguanidine-functionalized Fe3O4/Chloro-Silane Core-Shell nanoparticles: an efficient heterogeneous and reusable Organocatalyst for Aldol reaction. Silicon 11:1441
Meléndez-Ortiz HI, Mercado-Silva A, García-Cerda LA, Castruita G, Perera-Mercado YA (2013) Hydrothermal synthesis of Mesoporous silica MCM-41 using commercial sodium silicate. J. Mex. Chem. Soc. 57(2):73–79
Aziz MAA, Jalil AA, Triwahyono S, Mukti RR, Taufiq-Yap YH, Sazegar MR (2014) Highly active Ni-promoted mesostructured silica nanoparticles for CO2 methanation. Appl Catal B: Environ 147:359–368
Bacariza MC, Graça I, Bebiano SS, Lopesa JM, Henriques C (2018) Micro- and mesoporous supports for CO2 methanation catalysts: a comparison between SBA-15 MCM-41 and USY zeolite. Chem Eng J 175:72–83
Setnička M, Čičmanec P, Bulánek R, Zukal A, Pastva J (2014) Vanadium Mesoporous silica catalyst prepared by direct synthesis as high performing catalyst in oxidative dehydrogenation of n-butane. Catal Lett 144:50–55
Xu H, Yan J, Lu X, Yin J, Wu P (2018) Comparison of titanosilicates with different topologies as liquid-phase oxidation catalysts. Catal Today. https://doi.org/10.1016/jcattod201804026
Yokokawa M, Li T, Kambayashi M, Nakashima K, Hirayama Y, Okura H, Hasegawa M, Dertinger S, Kobayashi Y (2018) Silica-coating of quantum nanorods by a sol–gel process and their photo-bleaching properties. J Sol-Gel Sci Technol 86:773
Sazegar MR, Triwahyono S, Jalil AA, Mukti RR, Mohaghegh SMS, Aziz M (2015) High activity of aluminated bifunctional mesoporous silica nanoparticles for cumene hydrocracking and measurement of molar absorption coefficient. New J Chem 39:8006–8016
Sazegar MR, Dadvand A, Mahmoudi A (2017) Novel protonated Fe-containing mesoporous silica nanoparticle catalyst: excellent performance cyclohexane oxidation. RSC Adv 7:27506–27514
Sazegar MR, Jalil AA, Triwahyono S, Mukti RR, Aziz M, Aziz MAA, Kamarudin NHN, Setiabudi HD (2014) Protonation of Al-grafted mesostructured silica nanoparticles (MSN): acidity and catalytic activity for cumene conversion. Chem Eng J 240:352–361
Pal N, Bhaumik A (2015) Mesoporous materials: versatile supports in heterogeneous catalysis for liquid phase catalytic transformations. RSC Adv 5:24363–24391
Lai CY (2013) Mesoporous silica Nanomaterials applications in catalysis. J Thermodyn Catal 5:1
Trejda M, Ziolek M, Decyk P, Duczmal D (2009) The radical species and impurities present in mesoporous silicas as oxidation active centres. Microporous Mesoporous Mater 120:214–220
Sazegar MR, Mahmoudian SH, Mahmoudi A, Triwahyono S, Jalil AA, Mukti RR, Kamarudin NHN, Ghoreishi MK (2016) Catalyzed Claisen–Schmidt reaction by protonated aluminate mesoporous silica nanomaterial focused on the (E)-chalcone synthesis as a biologically active compound. RSC Adv 6:11023–11031
Robles-Dutenhefner PA, da Silva Rocha KA, Sousa EMB, Gusevskaya EV (2009) Cobalt-catalyzed oxidation of terpenes: co-MCM-41 as an efficient shape-selective heterogeneous catalyst for aerobic oxidation of isolongifolene under solvent-free conditions. J Catal 265:72–79
Fernandes DM, Silva R, Winkler Heichenletner AA (2009) Synthesis and characterization of ZnO CuO and a mixed Zn and cu oxide. Mater Chem Phys 115:110–115
Szegedi A, Popova M, Dimitrova A, Cherkezova-Zheleva Z, Mitov I (2010) Effect of the pre-treatment conditions on the physico-chemical and catalytic properties of cobalt- and iron-containing Ti-MCM-41 materials. Microporous Mesoporous Mater 136:106–114
Liu J, Zhang L, Yang Q, Li C (2008) Structural control of mesoporous silica with large nanopores in a mild buffer solution. Microporous Mesoporous Mater 116:330–338
Solovyov L (2013) A diffraction analysis of mesostructured mesoporous materials. Chem Soc Rev 42:3708–3720
Lee AF, Bennett JA, Manayil JC, Wilson K (2014) Heterogeneous catalysis for sustainable biodiesel production via esterification and. Chem Soc Rev 43:7887–7916
Roffia M, Padovan P, Moretti E, De Alberti G (1985) Catalytic process for preparing cyclohexanone-oxime US4745221A
Zhang QQ, Dong J, Liu YM, Cao Y, He HY, Wang YD (2017) An efficient noble-metal-free supported copper catalyst for selective nitrocyclohexane hydrogenation to cyclohexanone oxime. Chem Commun 53:2930–2933
Wang Y, Xin F, Yin Z, Song Y, Xiang T, Wang J (2018) Arginine-assisted hydrothermal synthesis of Urchinlike Nb2O5 nanostructures composed of nanowires and their application in Cyclohexanone Ammoximation. J Phys Chem C 122(4):2155–2164
Hu Y, Dong C, Wang T, Luo G (2018) Cyclohexanone ammoximation over TS-1 catalyst without organic solvent in a microreaction system. Chem Engin Sci 187:60–66
Damljanovic M, Vukic’ evic RD, Vukic’evic A (2006) Simple synthesis of Oximes. Monatsh Chem 137:301–305
Acknowledgements
We thanks from Islamic Azad University, North Tehran Branch for helping to performance of this study.
Author information
Authors and Affiliations
Corresponding authors
Additional information
Publisher’s Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Tayefe, H.C., Sazegar, M.R., Mahmoudi, A. et al. Co/Zn-Grafted Mesoporous Silica Nanoparticles Catalyzed Cyclohexanimine Oxidation under UV Irradiation: High Performance Ozonation Process. Silicon 13, 677–686 (2021). https://doi.org/10.1007/s12633-020-00464-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12633-020-00464-8