Baeyer–Villiger oxidation of cyclohexanone catalyzed by cordierite honeycomb washcoated with Mg–Sn–W composite oxides
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摘要
In this work, a series of Mg–Sn–W oxide powder catalysts with different tungsten oxide contents(0, 15 wt% and 30 wt%) were prepared and washcoated on cordierite honeycomb monoliths to produce monolithic catalysts,which were tested for the Baeyer–Villiger oxidation of cyclohexanone. The obtained monolithic catalysts,which combined the advantages of both homogeneous and heterogeneous catalysts, showed high catalytic efficiency and overcame the problems of product separation that occurred in the homogeneous catalytic process.SEM and EDX tests showed that the catalytic coating, with a thickness of approximately 20 μm, was compact and homogeneous, and an enlarged BET surface area was indicated by N_2 adsorption–desorption compared with the bare cordierite honeycomb. The chemical properties on the catalytic surface of the powder and monolithic catalysts were characterized by XPS, which indicated the tin and tungsten on the catalysts exhibited their full oxide states and presented mainly as stannate and tungstate, as confirmed by XRD and FTIR characterizations.Moreover, the catalytic activity test indicated that the tungsten content of the catalysts played an important role in catalytic efficiency and that monolithic catalysts were produced without obvious catalytic activity loss compared with the corresponding powders.(M)W30, which exhibited excellent mechanical stability and maintained high activity after recycling three times, was the optimal catalyst, showing a high selectivity that exceeded 86%and a conversion above 64%. Therefore, the structured Mg–Sn–W oxide catalysts have great potential for application in practical production.
In this work, a series of Mg–Sn–W oxide powder catalysts with different tungsten oxide contents(0, 15 wt% and 30 wt%) were prepared and washcoated on cordierite honeycomb monoliths to produce monolithic catalysts,which were tested for the Baeyer–Villiger oxidation of cyclohexanone. The obtained monolithic catalysts,which combined the advantages of both homogeneous and heterogeneous catalysts, showed high catalytic efficiency and overcame the problems of product separation that occurred in the homogeneous catalytic process.SEM and EDX tests showed that the catalytic coating, with a thickness of approximately 20 μm, was compact and homogeneous, and an enlarged BET surface area was indicated by N_2 adsorption–desorption compared with the bare cordierite honeycomb. The chemical properties on the catalytic surface of the powder and monolithic catalysts were characterized by XPS, which indicated the tin and tungsten on the catalysts exhibited their full oxide states and presented mainly as stannate and tungstate, as confirmed by XRD and FTIR characterizations.Moreover, the catalytic activity test indicated that the tungsten content of the catalysts played an important role in catalytic efficiency and that monolithic catalysts were produced without obvious catalytic activity loss compared with the corresponding powders.(M)W30, which exhibited excellent mechanical stability and maintained high activity after recycling three times, was the optimal catalyst, showing a high selectivity that exceeded 86%and a conversion above 64%. Therefore, the structured Mg–Sn–W oxide catalysts have great potential for application in practical production.
In this work, a series of Mg–Sn–W oxide powder catalysts with different tungsten oxide contents(0, 15 wt% and 30 wt%) were prepared and washcoated on cordierite honeycomb monoliths to produce monolithic catalysts,which were tested for the Baeyer–Villiger oxidation of cyclohexanone. The obtained monolithic catalysts,which combined the advantages of both homogeneous and heterogeneous catalysts, showed high catalytic efficiency and overcame the problems of product separation that occurred in the homogeneous catalytic process.SEM and EDX tests showed that the catalytic coating, with a thickness of approximately 20 μm, was compact and homogeneous, and an enlarged BET surface area was indicated by N_2 adsorption–desorption compared with the bare cordierite honeycomb. The chemical properties on the catalytic surface of the powder and monolithic catalysts were characterized by XPS, which indicated the tin and tungsten on the catalysts exhibited their full oxide states and presented mainly as stannate and tungstate, as confirmed by XRD and FTIR characterizations.Moreover, the catalytic activity test indicated that the tungsten content of the catalysts played an important role in catalytic efficiency and that monolithic catalysts were produced without obvious catalytic activity loss compared with the corresponding powders.(M)W30, which exhibited excellent mechanical stability and maintained high activity after recycling three times, was the optimal catalyst, showing a high selectivity that exceeded 86%and a conversion above 64%. Therefore, the structured Mg–Sn–W oxide catalysts have great potential for application in practical production.
引文
[1] K. Mandai, M. Hanata, K. Mitsudo, et al., Bacteriogenic iron oxide as an effective catalyst for Baeyer–Villiger oxidation with molecular oxygen and benzaldehyde, Tetrahedron 71(2015)9403–9407.
[2] Y. Ogasawara, S. Uchida, K. Yamaguchi, et al., A Tin-Tungsten mixed oxide as an ef-?cient heterogeneous catalyst for C-C bond-forming reactions, Chem. Eur. J. 15(2009)4343–4349.
[3] J.P. Mehta, D.K. Parmar, D.R. Godhani, et al., Heterogeneous catalysts hold the edge over homogeneous systems:Zeolite-Y encapsulated complexes for Baeyer–Villiger oxidation of cyclohexanone, J. Mol. Catal. A Chem. 421(2016)178–188.
[4] Y. Wang, T. Yokoi, R. Otomo, et al., Synthesis of Sn-containing mesoporous silica nanospheres as ef?cient catalyst for Baeyer–Villiger oxidation, Appl. Catal. A Gen.490(2015)93–100.
[5] R. Kumar, P.P. Das, A.S. Al-Fatesh, et al., Highly active In Ox/TUD-1 catalyst towards Baeyer–Villiger oxidation of cyclohexanone using molecular oxygen and benzaldehyde, Catal. Commun. 74(2016)80–84.
[6] M. Uyanik, K. Ishihara, Baeyer–Villiger oxidation using hydrogen peroxide, ACS Catal. 3(2013)513–520.
[7] H.Y. Lan, X.T. Zhou, H.B. Ji, Remarkable differences between benzaldehyde and isobutyraldehyde as coreductant in the performance toward the iron(III)porphyrins-catalyzed aerobic BaeyereVilliger oxidation of cyclohexanone, kinetic and mechanistic features, Tetrahedron 69(2013)4241–4246.
[8] R. Llamas, C. Jiménez-Sanchidrián, J.R. Ruiz, Heterogeneous Baeyer–Villiger oxidation of ketones with H2O2/nitrile using Mg/Al hydrotalcite as catalyst, Tetrahedron63(2007)1435–1439.
[9] R. Llamas, C. Jiménez-Sanchidrián, J.R. Ruiz, Environmentally friendly Baeyer–Villiger oxidation with H2O2/nitrile over Mg(OH)2and Mg O, Appl. Catal. B Environ.72(2007)18–25.
[10] M. Paul, N. Pal, J. Mondal, et al., New mesoporous magnesium–aluminum mixed oxide and its catalytic activity in liquid phase Baeyer–Villiger oxidation reaction,Chem. Eng. Sci. 71(2012)564–572.
[11] A. Corma, L.T. Nemeth, M. Renz, et al., Sn-zeolite beta as a heterogeneous chemoselective catalyst for Baeyer–Villiger oxidations, Nature 412(2001)423–425.
[12] J. Zang, Y. Ding, L. Yan, et al., Highly ef?cient and reusable Cu-MCM-41 catalyst for the Baeyer–Villiger oxidation of cyclohexanone, Catal. Commun. 51(2014)24–28.
[13] A.V. Malkov, F. Friscourt, M. Bell, et al., Enantioselective Baeyer–Villiger oxidation catalyzed by palladium(II)complexes with chiral P,N-ligands, J. Org. Chem. 73(2008)3996–4003.
[14] L.S. Martins, A.J.L. Pombeiro, C-scorpionate rhenium complexes and their application as catalysts in Baeyer–Villiger oxidation of ketones, Inorg. Chim. Acta 455(2016)390–397.
[15] J.R. Ruiz, C. Jiménez-Sanchidrián, R. Llamas, Hydrotalcites as catalysts for the Baeyer–Villiger oxidation of cyclic ketones with hydrogen peroxide/benzonitrile,Tetrahedron 62(2006)11697–11703.
[16] Z.Q. Qiang, Q.H. Zhang, J.J. Luo, et al., Baeyer–Villiger oxidation of ketones with hydrogen peroxide catalyzed by Sn-palygorskite, Tetrahedron Lett. 46(2005)3505–3508.
[17] Z.Q. Lei, G.F. Ma, C.G. Jia, Montmorillonite(MMT)supported tin(II)chloride:An ef-?cient and recyclable heterogeneous catalyst for clean and selective Baeyer–Villiger oxidation with hydrogen peroxide, Catal. Commun. 8(2007)305–309.
[18] J. Olszówka, R. Karcz, B. Napruszewska, et al., Magnesium and/or calcium-containing natural minerals as ecologically friendly catalysts for the Baeyer–Villiger oxidation of cyclohexanone with hydrogen peroxide, Appl. Catal. A Gen. 509(2016)52–65.
[19] R.S. Varma, Advances in green chemistry:Chemical syntheses using microwave irradiation, Tetrahedron 58(2002)1235–1255.
[20] C.G. Piscopo, S. Loebbecke, R. Maggi, et al., ChemInform abstract:Supported sulfonic acid as green and ef?cient catalyst for Baeyer–Villiger oxidation with 30%aqueous hydrogen peroxide, Adv. Synth. Catal. 352(2010)1625–1629.
[21] Q.G. Ma, L. Li, Y.X. Cao, et al., Sn–bentonite-induced Baeyer–Villiger oxidation of 2-heptylcyclopentanone toδ-dodecalactone with aqueous hydrogen peroxide, Res.Chem. Intermed. 41(2015)2249–2256.
[22] A. Dro?d?, A. Chrobok, S. Baj, et al., The chemo-enzymatic Baeyer–Villiger oxidation of cyclic ketones with an ef?cient silica-supported lipase as a biocatalyst, Appl. Catal.A Gen. 467(2013)163–170.
[23] K. Mandai, M. Hanata, K. Mitsudo, et al., ChemInform abstract:Bacteriogenic iron oxide as an effective catalyst for Baeyer–Villiger oxidation with molecular oxygen and benzaldehyde, ChemInform 47(2016)9403–9407.
[24] L.E. Gómez, I.S. Tiscornia, A.V. Boix, et al., Co/ZrO2catalysts coated on cordierite monoliths for CO preferential oxidation, Appl. Catal. A Gen. 401(2001)124–133.
[25] A. Vita, G. Cristiano, C. Italiano, et al., Methane oxy-steam reforming reaction:Performances of Ru/g-Al2O3catalysts loaded on structured cordierite monoliths, Int. J.Hydrog. Energy 39(2014)18592–18603.
[26] G. Grzybek, P. Stelmachowski, P. Indyka, et al., Cobalt–zinc spinel dispersed over cordierite monoliths for catalytic N2O abatement from nitric acid plants, Catal. Today257(2015)93–97.
[27] F. Li, B. Shen, L. Tian, et al., Enhancement of SCR activity and mechanical stability on cordierite supported V2O5–WO3/TiO2catalyst by substrate acid pretreatment and addition of silica, Powder Technol. 297(2016)384–391.
[28] Z.W. Xi, N. Zhou, Y. Sun, et al., Reaction-controlled phase-transfer catalysis for propylene epoxidation to propylene oxide, Science 292(2001)1139–1141.
[29] D.M. Gómez, J.M. Gatica, J.C. Hernández-Garrido, et al., A novel CoOx/La-modi?edCe O2formulation for powdered and washcoated onto cordierite honeycomb catalysts with application in VOCs oxidation, Appl. Catal. B Environ. 144(2014)425–434.
[30] B.M. Sollier, L.E. Gómez, A.V. Boix, et al., Oxidative coupling of methane on Sr/La2O3catalysts:Improving the catalytic performance using cordierite monoliths and ceramic foams as structured substrates, Appl. Catal. A Gen. 532(2017)65–76.
[31] E.D. Banus, M.A. Ulla, E.E. Miro, et al., Structured catalysts for soot combustion for diesel engines, Diesel Engine 2013, pp. 117–142.
[32] A.K. Mogalicherla, D. Kunzru, The effect of prewetting on the loading of c-alumina washcoated cordierite monolith, Int. J. Appl. Ceram. Technol. 8(2011)430–436.
[33] P. Avila, M. Montes, E.E. Miró, Monolithic reactors for environmental applications:A review on preparation technologies, Chem. Eng. J. 109(2005)11–36.
[34] L.E. Gómez, I.S. Tiscornia, A.V. Boix, et al., CO preferential oxidation on cordierite monoliths coated with Co/CeO2catalysts, Int. J. Hydrog. Energy 37(2012)14812–14819.
[35] C. Plana, S. Armenise, A. Monzón, et al., Ni on alumina-coated cordierite monoliths for in situ generation of CO-free H2from ammonia, J. Catal. 275(2010)228–235.
[36] J. Wang, L. Ye, M. Jin, X. Wang, Global analyses of Chromosome 17 and 18 genes of lung telocytes compared with mesenchymal stem cells,?broblasts, alveolar type II cells, airway epithelial cells, and lymphocytes, Biol. Direct 10(2015)9.
[37] G.X. Zhang, X.C. Ren, H.B. Zhang, et al., MgO/SnO2/WO3as catalysts for synthesis ofε-caprolactone over oxidation of cyclohexanone with peracetic acid, Catal. Commun.58(2015)59–63.
[38] O.A. Al-Harbi, C.?zgür, M.M. Khan, Fabrication and characterization of single phase cordierite honeycomb monolith with porous wall from natural raw materials as catalyst support, Ceram. Int. 41(2015)3526–3532.
[39] R.A. Steffen, S. Teixeira, J. Sepulveda, et al., Alumina-catalyzed Baeyer–Villiger oxidation of cyclohexanone with hydrogen peroxide, J. Mol. Catal. A Chem. 287(2008)41–44.
[40] P. Brussino, J.P. Bortolozzi, V.G. Milt, et al., NiCe/r-Al2O3coated onto cordierite monoliths applied to Oxidative Dehydrogenation of Ethane(ODE), Catal. Today273(2016)259–265.
[41] Z. Yang, L. Niu, Z. Ma, et al., Fabrication of highly active Sn/W mixed transition-metal oxides as solid acid catalysts, Transit. Met. Chem. 36(2011)269–274.
[42] S. Rahman, S.A. Farooqui, A. Rai, et al., Mesoporous TUD-1 supported indium oxide nanoparticles for epoxidation of styrene using molecular O2, RSC Adv. 5(2015)46850–46860.
[43] Q. Tian, W. Wu, L. Sun, et al., Tube-like ternaryα-Fe2O3@SnO2@Cu2O sandwich heterostructures:Synthesis and enhanced photocatalytic properties, ACS Appl.Mater. Interfaces 6(2014)13088–13097.
[44] N. Wang, Y. Du, W. Ma, et al., Rational design and synthesis of SnO2-encapsulatedα-Fe2O3nanocubes as a robust and stable photo-Fenton catalyst, Appl. Catal. B Environ.210(2017)23–33.
[45] S. Zhang, Q. Zhong, Y. Shen, et al., New insight into the promoting role of process on the CeO2–WO3/TiO2catalyst for NO reduction with NH3at low-temperature, J. Colloid Interface Sci. 448(2015)417–426.
[46] S. Zhang, Q. Zhong, Surface characterization studies on the interaction of V2O5–WO3/TiO2catalyst for low temperature SCR of NO with NH3, J. Solid State Chem.221(2015)49–56.
[47] B. Liu, J. Du, X. Lv, et al., Washcoating of cordierite honeycomb with vanadia–tungsta–titania mixed oxides for selective catalytic reduction of NO with NH3,Catal. Sci. Technol. 5(2015)1241–1250.
[48] L. Zong, F. Dong, G. Zhang, et al., Highly ef?cient mesoporous V2O5/WO3–TiO2catalyst for selective catalytic reduction of NOx:Effect of the valence of V on the catalytic performance, Catal. Surv. Jpn. 21(2017)103–113.
[49] V.I. Alexiadis, J.W. Thybaut, P.N. Kechagiopoulos, et al., Oxidative coupling of methane:Catalytic behaviour assessment via comprehensive microkinetic modelling,Appl. Catal. B Environ. 150-151(2014)496–505.
[2] Y. Ogasawara, S. Uchida, K. Yamaguchi, et al., A Tin-Tungsten mixed oxide as an ef-?cient heterogeneous catalyst for C-C bond-forming reactions, Chem. Eur. J. 15(2009)4343–4349.
[3] J.P. Mehta, D.K. Parmar, D.R. Godhani, et al., Heterogeneous catalysts hold the edge over homogeneous systems:Zeolite-Y encapsulated complexes for Baeyer–Villiger oxidation of cyclohexanone, J. Mol. Catal. A Chem. 421(2016)178–188.
[4] Y. Wang, T. Yokoi, R. Otomo, et al., Synthesis of Sn-containing mesoporous silica nanospheres as ef?cient catalyst for Baeyer–Villiger oxidation, Appl. Catal. A Gen.490(2015)93–100.
[5] R. Kumar, P.P. Das, A.S. Al-Fatesh, et al., Highly active In Ox/TUD-1 catalyst towards Baeyer–Villiger oxidation of cyclohexanone using molecular oxygen and benzaldehyde, Catal. Commun. 74(2016)80–84.
[6] M. Uyanik, K. Ishihara, Baeyer–Villiger oxidation using hydrogen peroxide, ACS Catal. 3(2013)513–520.
[7] H.Y. Lan, X.T. Zhou, H.B. Ji, Remarkable differences between benzaldehyde and isobutyraldehyde as coreductant in the performance toward the iron(III)porphyrins-catalyzed aerobic BaeyereVilliger oxidation of cyclohexanone, kinetic and mechanistic features, Tetrahedron 69(2013)4241–4246.
[8] R. Llamas, C. Jiménez-Sanchidrián, J.R. Ruiz, Heterogeneous Baeyer–Villiger oxidation of ketones with H2O2/nitrile using Mg/Al hydrotalcite as catalyst, Tetrahedron63(2007)1435–1439.
[9] R. Llamas, C. Jiménez-Sanchidrián, J.R. Ruiz, Environmentally friendly Baeyer–Villiger oxidation with H2O2/nitrile over Mg(OH)2and Mg O, Appl. Catal. B Environ.72(2007)18–25.
[10] M. Paul, N. Pal, J. Mondal, et al., New mesoporous magnesium–aluminum mixed oxide and its catalytic activity in liquid phase Baeyer–Villiger oxidation reaction,Chem. Eng. Sci. 71(2012)564–572.
[11] A. Corma, L.T. Nemeth, M. Renz, et al., Sn-zeolite beta as a heterogeneous chemoselective catalyst for Baeyer–Villiger oxidations, Nature 412(2001)423–425.
[12] J. Zang, Y. Ding, L. Yan, et al., Highly ef?cient and reusable Cu-MCM-41 catalyst for the Baeyer–Villiger oxidation of cyclohexanone, Catal. Commun. 51(2014)24–28.
[13] A.V. Malkov, F. Friscourt, M. Bell, et al., Enantioselective Baeyer–Villiger oxidation catalyzed by palladium(II)complexes with chiral P,N-ligands, J. Org. Chem. 73(2008)3996–4003.
[14] L.S. Martins, A.J.L. Pombeiro, C-scorpionate rhenium complexes and their application as catalysts in Baeyer–Villiger oxidation of ketones, Inorg. Chim. Acta 455(2016)390–397.
[15] J.R. Ruiz, C. Jiménez-Sanchidrián, R. Llamas, Hydrotalcites as catalysts for the Baeyer–Villiger oxidation of cyclic ketones with hydrogen peroxide/benzonitrile,Tetrahedron 62(2006)11697–11703.
[16] Z.Q. Qiang, Q.H. Zhang, J.J. Luo, et al., Baeyer–Villiger oxidation of ketones with hydrogen peroxide catalyzed by Sn-palygorskite, Tetrahedron Lett. 46(2005)3505–3508.
[17] Z.Q. Lei, G.F. Ma, C.G. Jia, Montmorillonite(MMT)supported tin(II)chloride:An ef-?cient and recyclable heterogeneous catalyst for clean and selective Baeyer–Villiger oxidation with hydrogen peroxide, Catal. Commun. 8(2007)305–309.
[18] J. Olszówka, R. Karcz, B. Napruszewska, et al., Magnesium and/or calcium-containing natural minerals as ecologically friendly catalysts for the Baeyer–Villiger oxidation of cyclohexanone with hydrogen peroxide, Appl. Catal. A Gen. 509(2016)52–65.
[19] R.S. Varma, Advances in green chemistry:Chemical syntheses using microwave irradiation, Tetrahedron 58(2002)1235–1255.
[20] C.G. Piscopo, S. Loebbecke, R. Maggi, et al., ChemInform abstract:Supported sulfonic acid as green and ef?cient catalyst for Baeyer–Villiger oxidation with 30%aqueous hydrogen peroxide, Adv. Synth. Catal. 352(2010)1625–1629.
[21] Q.G. Ma, L. Li, Y.X. Cao, et al., Sn–bentonite-induced Baeyer–Villiger oxidation of 2-heptylcyclopentanone toδ-dodecalactone with aqueous hydrogen peroxide, Res.Chem. Intermed. 41(2015)2249–2256.
[22] A. Dro?d?, A. Chrobok, S. Baj, et al., The chemo-enzymatic Baeyer–Villiger oxidation of cyclic ketones with an ef?cient silica-supported lipase as a biocatalyst, Appl. Catal.A Gen. 467(2013)163–170.
[23] K. Mandai, M. Hanata, K. Mitsudo, et al., ChemInform abstract:Bacteriogenic iron oxide as an effective catalyst for Baeyer–Villiger oxidation with molecular oxygen and benzaldehyde, ChemInform 47(2016)9403–9407.
[24] L.E. Gómez, I.S. Tiscornia, A.V. Boix, et al., Co/ZrO2catalysts coated on cordierite monoliths for CO preferential oxidation, Appl. Catal. A Gen. 401(2001)124–133.
[25] A. Vita, G. Cristiano, C. Italiano, et al., Methane oxy-steam reforming reaction:Performances of Ru/g-Al2O3catalysts loaded on structured cordierite monoliths, Int. J.Hydrog. Energy 39(2014)18592–18603.
[26] G. Grzybek, P. Stelmachowski, P. Indyka, et al., Cobalt–zinc spinel dispersed over cordierite monoliths for catalytic N2O abatement from nitric acid plants, Catal. Today257(2015)93–97.
[27] F. Li, B. Shen, L. Tian, et al., Enhancement of SCR activity and mechanical stability on cordierite supported V2O5–WO3/TiO2catalyst by substrate acid pretreatment and addition of silica, Powder Technol. 297(2016)384–391.
[28] Z.W. Xi, N. Zhou, Y. Sun, et al., Reaction-controlled phase-transfer catalysis for propylene epoxidation to propylene oxide, Science 292(2001)1139–1141.
[29] D.M. Gómez, J.M. Gatica, J.C. Hernández-Garrido, et al., A novel CoOx/La-modi?edCe O2formulation for powdered and washcoated onto cordierite honeycomb catalysts with application in VOCs oxidation, Appl. Catal. B Environ. 144(2014)425–434.
[30] B.M. Sollier, L.E. Gómez, A.V. Boix, et al., Oxidative coupling of methane on Sr/La2O3catalysts:Improving the catalytic performance using cordierite monoliths and ceramic foams as structured substrates, Appl. Catal. A Gen. 532(2017)65–76.
[31] E.D. Banus, M.A. Ulla, E.E. Miro, et al., Structured catalysts for soot combustion for diesel engines, Diesel Engine 2013, pp. 117–142.
[32] A.K. Mogalicherla, D. Kunzru, The effect of prewetting on the loading of c-alumina washcoated cordierite monolith, Int. J. Appl. Ceram. Technol. 8(2011)430–436.
[33] P. Avila, M. Montes, E.E. Miró, Monolithic reactors for environmental applications:A review on preparation technologies, Chem. Eng. J. 109(2005)11–36.
[34] L.E. Gómez, I.S. Tiscornia, A.V. Boix, et al., CO preferential oxidation on cordierite monoliths coated with Co/CeO2catalysts, Int. J. Hydrog. Energy 37(2012)14812–14819.
[35] C. Plana, S. Armenise, A. Monzón, et al., Ni on alumina-coated cordierite monoliths for in situ generation of CO-free H2from ammonia, J. Catal. 275(2010)228–235.
[36] J. Wang, L. Ye, M. Jin, X. Wang, Global analyses of Chromosome 17 and 18 genes of lung telocytes compared with mesenchymal stem cells,?broblasts, alveolar type II cells, airway epithelial cells, and lymphocytes, Biol. Direct 10(2015)9.
[37] G.X. Zhang, X.C. Ren, H.B. Zhang, et al., MgO/SnO2/WO3as catalysts for synthesis ofε-caprolactone over oxidation of cyclohexanone with peracetic acid, Catal. Commun.58(2015)59–63.
[38] O.A. Al-Harbi, C.?zgür, M.M. Khan, Fabrication and characterization of single phase cordierite honeycomb monolith with porous wall from natural raw materials as catalyst support, Ceram. Int. 41(2015)3526–3532.
[39] R.A. Steffen, S. Teixeira, J. Sepulveda, et al., Alumina-catalyzed Baeyer–Villiger oxidation of cyclohexanone with hydrogen peroxide, J. Mol. Catal. A Chem. 287(2008)41–44.
[40] P. Brussino, J.P. Bortolozzi, V.G. Milt, et al., NiCe/r-Al2O3coated onto cordierite monoliths applied to Oxidative Dehydrogenation of Ethane(ODE), Catal. Today273(2016)259–265.
[41] Z. Yang, L. Niu, Z. Ma, et al., Fabrication of highly active Sn/W mixed transition-metal oxides as solid acid catalysts, Transit. Met. Chem. 36(2011)269–274.
[42] S. Rahman, S.A. Farooqui, A. Rai, et al., Mesoporous TUD-1 supported indium oxide nanoparticles for epoxidation of styrene using molecular O2, RSC Adv. 5(2015)46850–46860.
[43] Q. Tian, W. Wu, L. Sun, et al., Tube-like ternaryα-Fe2O3@SnO2@Cu2O sandwich heterostructures:Synthesis and enhanced photocatalytic properties, ACS Appl.Mater. Interfaces 6(2014)13088–13097.
[44] N. Wang, Y. Du, W. Ma, et al., Rational design and synthesis of SnO2-encapsulatedα-Fe2O3nanocubes as a robust and stable photo-Fenton catalyst, Appl. Catal. B Environ.210(2017)23–33.
[45] S. Zhang, Q. Zhong, Y. Shen, et al., New insight into the promoting role of process on the CeO2–WO3/TiO2catalyst for NO reduction with NH3at low-temperature, J. Colloid Interface Sci. 448(2015)417–426.
[46] S. Zhang, Q. Zhong, Surface characterization studies on the interaction of V2O5–WO3/TiO2catalyst for low temperature SCR of NO with NH3, J. Solid State Chem.221(2015)49–56.
[47] B. Liu, J. Du, X. Lv, et al., Washcoating of cordierite honeycomb with vanadia–tungsta–titania mixed oxides for selective catalytic reduction of NO with NH3,Catal. Sci. Technol. 5(2015)1241–1250.
[48] L. Zong, F. Dong, G. Zhang, et al., Highly ef?cient mesoporous V2O5/WO3–TiO2catalyst for selective catalytic reduction of NOx:Effect of the valence of V on the catalytic performance, Catal. Surv. Jpn. 21(2017)103–113.
[49] V.I. Alexiadis, J.W. Thybaut, P.N. Kechagiopoulos, et al., Oxidative coupling of methane:Catalytic behaviour assessment via comprehensive microkinetic modelling,Appl. Catal. B Environ. 150-151(2014)496–505.