Abstract
Several types of mixed molybdenum and tungsten oxide—SiO2 materials were prepared using sol–gel and wet impregnation method. In all cases, four different loading of MoO3 or WO3 (1, 10, 25 and 40 wt%) were prepared. Materials were characterized using X-ray diffraction, X-ray fluorescence spectroscopy and its acidity was determined by temperature programmed desorption of pyridine. Catalytic activity of these materials was tested in three model reactions providing valuable fine chemicals—aldol condensation, acetalization and esterification. These reactions are usually catalyzed by homogenous catalysts. With increasing interest in environmental protection these catalysts are replaced by heterogeneous ones—offering easy separation from reaction mixture and a possibility of catalyst reuse. More specifically the chosen reactions were: aldol condensation of benzaldehyde with heptanal giving jasmine aldehyde (1), acetalization of heptanal by ethylene glycol giving 2-hexyl-1,3-dioxolane (2) and esterification of lauric acid by methanol giving methyllaurate (3). The prepared materials proved to be catalytically active in above mentioned reactions—in aldol condensation was the best result (78% heptanal conversion, 58% selectivity to jasmine aldehyde, 24 h) obtained using Mo 40 material prepared by impregnation. This material showed to be the best together with W 40 material prepared by sol–gel process in esterification (91 or 94% conversion, 24 h). Acetalization occurs very willingly, best results (heptanal conversion > 90% and selectivity > 90%, 5 h) was obtained using Mo and W 25 and 40 prepared by sol–gel and impregnation process.
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Ma Z, Wei L, Zhou W, Hou LJB, Li D, Zhao Y (2015) RSC Adv 5:88287–88297
Primo A, Garcia H (2014) Chem Soc Rev 43:7548–7561
Roessler F (1996) Chimia 50:106–109
Lee MJ, Chiu JY, Lin HM (2002) Ind Eng Chem Res 41:2882–2887
Mya OB, Bita M, Louafi I, Djouad A (2018) MethodsX 5:277–282
Khire S, Bhagwat PV, Fernandes M, Gangund PB, Vadalia H (2012) Indian J Chem Technol 19:342–350
Brahmkhatri V, Pate A (2010) Kinet Catal -Engl Tr 51:380–384
Sekerová L, Lhotka M, Vyskočilová E, Faukner T, Slováková E, Brus J, Červený L, Sedláček J (2018) Chem Eur J 24:14742–14749
Tišler Z, Vrbková E, Kocík J, Kadlec D, Vyskočilová E, Červený L (2018) Catal Lett 148:2042–2057
Vrbková E, Vyskočilová E, Červený L (2015) React Kinet. Mech Catal 114:675–684
Vyskočilová E, Rezková L, Vrbková E, Paterová I, Červený L (2016) Res Chem Intermed 42:725–733
Vyskočilová E, Sekerová L, Paterová I, Krupka J, Veselý M, Červený L (2018) J Porous Mater 25:273–283
Vyskočilová E, Gruberová A, Shamzhy M, Vrbková E, Krupka J, Červený L (2018) React Kinet. Mech Catal 124:711–725
Sekerová L, Vyskočilová E, Fantova JS, Paterová I, Krupka J, Červený L (2017) Res Chem Intermed 43:4943–4958
Luštická I, Vrbková E, Vyskočilová E, Paterová I, Červený L (2013) React Kinet. Mech Catal 108:205–2012
Chandra KL, Saravanan P, Singh RK, Singh VK (2002) Tetrahedron 58:1369–1374 (2002).
Sekerová L, Spáčilová M, Vyskočilová E, Krupka J, Červený L (2019) React Kinet Mech Catal 127:727–740
Moghaddam FM, Sharifi A (1995) Synth Commun 25:2457–2461
Zhao S, Jia Y, Song YF (2014) Catal Sci Techno. 4:2618–2625
Vyskočilová E, Hašková L, Červený L (2019) Chem Pap 73:1621–1627
Vyskočilová E, Dušek J, Babiradová M, Krupka J, Paterova I, Červený L (2018) Res Chem Intermed 44:3971–3984
Vyskočilová E, Malý M, Aho A, Krupka J, Červený L (2016) React Kinet. Mech Catal 118:235–246
Štekrová M, Kubů M, Shamzhy M, Musilová Z, Čejka J (2018) Catal Sci Technol 8:2488–2501
Song Z, Minura N, Tsubota S, Fujitani T, Oyama ST (2008) Catal Let. 121:33–38
Štekrová M, Minariková H, Vyskočilová E, Kolena J, Červený L (2014) J Porous Mater 21:757–767
Auroux A, Gervasini A (1990) J Phys Chem 94:6371–6379
Wang Z (2014) WangL, Jiang Y, Hunger M, HuangJ. ACS Catal 4:1144–1147
Amrute AP, Bordoloi A, Lucas N, Palraj K, Halligudi SB (2008) Catal Lett 126:286–292
Maksasithorn S, Praserthdam P, Suriye K, Debecker DP (2015) Microporous Mesoporous Mater 213:125–133
Umbarkar SB, Kotbagi TV, Biradar AV, Pasricha R, Chanale J, Dongare MK, Mamede AS, Lancelot C, Payen E (2009) J Mol Catal A: Chem 310:150–158
Huang X, Liu J, Chen J, Xu Y, Shen W (2006) Catal Lett 108:79–86
Marakatti VS, Mumbaraddi D, Shanbhag GV, Halgeri AB, Maradur SP (2015) RSC Adv 5:93452–93462
Kočovský P, Ahmed G, Šrogl J, Malkov AV, Steele J (1999) J Org Chem 64:2765–2775
Chen K, Bell AT, Iglesia E (2002) J Catal 209:35–42
Ji W, Chen Y, Kung HH (1997) App Cat A: Gen 161:93–104
Signore NR, Anandgaonker PL, Gaikwad ST, Rajbhoj AS (2015) Mater Sci-Pol 33:163–168
Somma F, Struku G (2004) J Cata. 227:344–351
Dube TI, Moodley DJ, van Schalkwyk C, Botha JM (2003) App Cat A: Gen 255:133–142
Bouhoute Y, Grekov D, Szeto KC, Merle N, de Mallmann A, Lefebvre F, Raffa G, del Rosal I, Maron L, Gauvin RM, Delevoye L, Taoufik M (2016) ACS Catal 6:1–18
Mishra G, Behera GC, Singh SK, Parida KM (2012) Dalton Trans 41:14299–14308
Park YM, Lee JY, Chung SH, Park IS, Lee SY, Kim DK, Lee JS, Lee KY (2010) Bioresour Technol 101:s59–s61
Smirnov AA, Selishcheva SA, Yakovlev VA (2018) Catalysts 8(595):1–25
Maerker G, Kenney HE, Bilyk A, Ault WC (1966) J Am Oil Chem Soc 43:104–107
Han B, Zhang W, Yin F, Liu S, Zhao X, Liu J, Wang C, Yang H (2018) R Soc Open Sci 5(180672):1–16
Han B, Yin F, Liu S, Zhao X, Liu J, Wang C, Yang H, Zhang W (2018) Int J Chem React Eng 17(20180144):1–12
Sekerová L, Vyskočilová E, Červený L (2017) React Kinet. Mech Catal 12:83–95
Swanson HE, Fuyat RK (1954) Standard X-ray diffraction powder patterns, National bureau of standards.
Salje E (1977) Acta Crystallogr 33:574–577
Oi J, Kishimoto A, Kudo T, Hiratani M (1992) J Solid State Chem. 96:13–19
Vrbková E, Tišler Z, Vyskočilová E, Kadlec D, Červený L (2018) J Chem Technol Biotechnol 93:166–173 (2018)
Kim DS, Ostromecki M, Wachs IE (1995) Catal Lett 33:209–215
Hollak SAW, Gosselink RW, van Es DS, Bitter JH (2017) ACS Catal 3:2837–2844
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Vrbková, E., Šteflová, B., Sekerová, L. et al. Contribution to MoO3–SiO2 and WO3–SiO2 utilization—active catalysts in jasmine aldehyde, 2-hexyl-1,3-dioxolane and methyllaurate synthesis. Reac Kinet Mech Cat 129, 645–658 (2020). https://doi.org/10.1007/s11144-020-01727-6
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DOI: https://doi.org/10.1007/s11144-020-01727-6