Abstract
In this paper, a sequence of ordered mesoporous chromium–zirconium oxophosphate (M–Cr–ZrPO) composites with controllable chromium contents (0–15 mol%) were projected and successfully synthesized through a modified one-pot evaporation-induced self-assembly method. Characterized by N2 adsorption–desorption isotherms and TEM techniques, the resultant M–Cr–ZrPO composites owned ordered mesoporous structure and the textural properties [specific surface areas (160–210 m2 g−1), pore volumes (0.25–0.28 cm3 g−1) and pore sizes (5.6–6.6 nm)] of materials were improved by the introduced chromium species. In addition, the dispersion, existing states and contents of introduced chromium species in the materials were researched in detail by elemental mapping images, XRD, UV–vis, FT-IR, XPS and H2-TPR techniques. All the characterizations implied that the chromium oxides were introduced as expected and homogeneously dispersed in the skeleton of mesoporous materials. Owing to the outstanding structural properties and chromium species with homogeneous dispersion, the M–Cr–ZrPO materials exhibited superior catalytic activity for liquid phase oxidation of benzyl alcohol and ethylbenzene.
Similar content being viewed by others
References
Zhang Y, Cui X, Shi F, Deng Y (2012) Nano-gold catalysis in fine chemical synthesis. Chem Rev 112:2467–2505
Punniyamurthy T, Rout L (2008) Recent advances in copper-catalyzed oxidation of organic compounds. Coordin Chem Rev 252:134–154
Bokare AD, Choi W (2014) Review of iron-free Fenton-like systems for activating H2O2 in advanced oxidation processes. J Hazard Mater 275:121–135
Zamani F, Hosseini SM, Kianpour S (2014) Cr(III)-containing Fe3O4/mercaptopropanoic acid-poly (2-hydroxyethyl acrylate) nanocomposite: a highly active magnetic catalyst in solvent-free aerobic oxidation of alcohols. Dalton Trans 43:3618–3625
Davis SE, Ide MS, Davis RJ (2013) Selective oxidation of alcohols and aldehydes over supported metal nanoparticles. Green Chem 15:17–45
Parmeggiani C, Cardona F (2012) Transition metal based catalysts in the aerobic oxidation of alcohols. Green Chem 14:547–564
Zhang Z, Liu B, Lv K, Sun J, Deng K (2014) Aerobic oxidation of biomass derived 5-hydroxymethylfurfural into 5-hydroxymethyl-2-furancarboxylic acid catalyzed by a montmorillonite K-10 clay immobilized molybdenum acetylacetonate complex. Green Chem 16:2762–2770
Wang S, Zhang Z, Liu B (2015) Catalytic conversion of fructose and 5-hydroxymethylfurfural into 2,5-furandicarboxylic acid over a recyclable Fe3O4–CoOx magnetite nanocatalyst. ACS Sustainable Chem Eng 3:406–412
Mandi U, Pramanik M, Singha Roy A, Salam N, Bhaumik A, Islam SM (2014) Chromium(VI) grafted mesoporous polyaniline as a reusable heterogeneous catalyst for oxidation reactions in aqueous medium. RSC Adv 4:15431–15440
Li K, Zhou D, Deng J, Lu X, Xia Q (2014) Highly efficient catalytic oxidation of cyclohexanol with TBHP over Cr-13X catalysts in a solvent-free system. J Mol Catal A 387:31–37
Bekish AV (2012) Carbon–carbon bond fission on oxidation of primary alcohols to carboxylic acids. Tetrahedron Lett 53:3082–3085
Long J, Liu H, Wu S, Liao S, Li Y (2013) Selective oxidation of saturated hydrocarbons using Au–Pd alloy nanoparticles supported on metal-organic frameworks. ACS Catal 3:647–654
Pal N, Cho EB, Kim D (2014) Synthesis of ordered mesoporous silica/ceria-silica composites and their high catalytic performance for solvent-free oxidation of benzyl alcohol at room temperature. RSC Adv 4:9213–9222
Liu P, Degirmenci V, Hensen EJM (2014) Unraveling the synergy between gold nanoparticles and chromium-hydrotalcites in aerobic oxidation of alcohols. J Catal 313:80–91
Mohapatra SK, Selvam P (2007) A highly selective, heterogeneous route to enones from allylic and benzylic compounds over mesoporous CrMCM-41 molecular sieves. J Catal 249:394–396
Habibi D, Faraji AR, Arshadi M, Fierro JLG (2013) Characterization and catalytic activity of a novel Fe nano-catalyst as efficient heterogeneous catalyst for selective oxidation of ethylbenzene, cyclohexene, and benzylalcohol. J Mol Catal A 372:90–99
Mannam S, Sekar G (2008) CuCl catalyzed selective oxidation of primary alcohols to carboxylic acids with tert-butyl hydroperoxide at room temperature. Tetrahedron Lett 49:2457–2460
Chen H, Deng Y, Yu Z, Zhao H, Yao Q, Zou X, Bäckvall JE, Sun J (2013) 3D open-framework vanadoborate as a highly effective heterogeneous pre-catalyst for the oxidation of alkylbenzenes. Chem Mater 25:5031–5036
Guo Z, Liu B, Zhang Q, Deng W, Wang Y, Yang Y (2014) Recent advances in heterogeneous selective oxidation catalysis for sustainable chemistry. Chem Soc Rev 43:3480–3524
Wang A, Guo Y, Gao F, Peden CHF (2017) Ambient-temperature NO oxidation over amorphous CrOx–ZrO2 mixed oxide catalysts: Significant promoting effect of ZrO2. Appl Catal B 202:706–714
Ma F, Chen S, Wang Y, Chen F, Lu W (2012) Characterization of redox and acid properties of mesoporous Cr-TiO2 and its efficient performance for oxidative dehydrogenation of propane. Appl Catal A 427–428:145–154
Heidarnezhad A, Zamani F (2015) Chromium containing Fe3O4/polyacrylonitrile-ethylenediamine as a magnetically recoverable catalyst for alcohol oxidation. Catal Commun 60:105–109
Khan IA, Ullah S, Nasim F, Choucair M, Nadeem MA, Iqbal A, Badshah A, Nadeem MA (2016) Cr2O3-carbon composite as a new support material for efficient methanol electrooxidation. Mater Res Bull 77:221–227
Wee LH, Bonino F, Lamberti C, Bordiga S, Martens JA (2014) Cr-MIL-101 encapsulated Keggin phosphotungstic acid as active nanomaterial for catalysing the alcoholysis of styrene oxide. Green Chem 16:1351–1357
Zhao H, Song H, Xu L, Chou L (2013) Isobutane dehydrogenation over the mesoporous Cr2O3/Al2O3 catalysts synthesized from a metal-organic framework MIL-101. Appl Catal A 456:188–196
Liu B, Ba C, Jin M, Zhang Z (2015) Effective conversion of carbohydrates into biofuel precursor 5-hydroxymethylfurfural (HMF) over Cr-incorporated mesoporous zirconium phosphate. Ind Crop Prod 76:781–786
Xia P, Zuo S, Liu F, Qi C (2013) Ceria modified crystalline mesoporous Cr2O3 based nanocomposites supported metal oxide for benzene complete oxidation. Catal Commun 41:91–95
Tamiolakis I, Lykakis IN, Katsoulidis AP, Stratakis M, Armatas GS (2011) Mesoporous Cr2O3-phosphomolybdic acid solid solution frameworks with high catalytic activity. Chem Mater 23:4204–4211
Wu Z, Deng J, Xie S, Yang H, Zhao X, Zhang K, Lin H, Dai H, Guo G (2016) Mesoporous Cr2O3-supported Au-Pd nanoparticles: high-performance catalysts for the oxidation of toluene. Micropor Mesopor Mater 224:311–322
Michorczyk P, Pietrzyk P, Ogonowski J (2012) Preparation and characterization of SBA-1-supported chromium oxide catalysts for CO2 assisted dehydrogenation of propane. Micropor Mesopor Mater 161:56–66
Xia Y, Dai H, Jiang H, Deng J, He H, Au CT (2009) Mesoporous chromia with ordered three-dimensional structures for the complete oxidation of toluene and ethyl acetate. Environ Sci Technol 43:8355–8360
Sarkadi-Priboczki E, Tsoncheva T (2012) 11C-Radiolabeling study of methanol decomposition on chromium modified SBA-15 silica. J Porous Mater 19:705–711
He F, Luo J, Liu S (2016) Novel metal loaded KIT-6 catalysts and their applications in the catalytic combustion of chlorobenzene. Chem Eng J 294:362–370
Ooi YK, Yuliati L, Lee SL (2016) Phenol photocatalytic degradation over mesoporous TUD-1-supported chromium oxide-doped titania photocatalyst. Chin J Catal 37:1871–1881
Baek J, Yun HJ, Yun D, Choi Y, Yi J (2012) Preparation of highly dispersed chromium oxide catalysts supported on mesoporous silica for the oxidative dehydrogenation of propane using CO2: insight into the nature of catalytically active chromium sites. ACS Catal 2:1893–1903
Kruk M, Jaroniec M, Sayari A (1997) Application of large pore MCM-41 molecular sieves to improve pore size analysis using nitrogen adsorption measurements. Langmuir 13:6267–6273
Cai W, Yu J, Anand C, Vinu A, Jaroniec M (2011) Facile synthesis of ordered mesoporous alumina and alumina-supported metal oxides with tailored adsorption and framework properties. Chem Mater 23:1147–1157
Kruk M, Jaroniec M (2001) Gas adsorption characterization of ordered organic–inorganic nanocomposite materials. Chem Mater 13:3169–3183
Shee D, Sayari A (2010) Light alkane dehydrogenation over mesoporous Cr2O3/Al2O3 catalysts. Appl Catal A 389:155–164
Das SK, Bhunia MK, Sinha AK, Bhaumik A (2011) Synthesis, characterization, and biofuel application of mesoporous zirconium oxophosphates. ACS Catal 1:493–501
Sinhamahapatra A, Sutradhar N, Pahari SK, Pal P, Bajaj HC, Jayachandran M, Panda AB (2011) Allylic and benzylic oxidation over CrIII-incorporated mesoporous zirconium phosphate with 100% selectivity. ChemCatChem 3:1447–1450
Wang J, Xie J, Zhou Y, Wang J (2013) New facile way to isomorphously substituted Cr-β zeolite and its catalytic performance. Micropor Mesopor Mater 171:87–93
Kang KH, Kim TH, Choi WC, Park YK, Hong UG, Park DS, Kim CJ, Song IK (2015) Dehydrogenation of propane to propylene over CrOy–CeO2–K2O/γ–Al2O3 catalysts: effect of cerium content. Catal Commun 72:68–72
Jiménez-López A, Rodríguez-Castellón E, Maireles-Torres P, Díaz L, Mérida-Robles J (2001) Chromium oxide supported on zirconium- and lanthanum-doped mesoporous silica for oxidative dehydrogenation of propane. Appl Catal A 218:295–306
Tamiolakis I, Lykakis IN, Katsoulidis AP, Malliakas CD, Armatas GS (2012) Ordered mesoporous Cr2O3 frameworks incorporating Keggin-type 12-phosphotungstic acids as efficient catalysts for oxidation of benzyl alcohols. J Mater Chem 22:6919–6927
Liu Q, He H, Chao ZS, Xie J, Ruchenstein E (2012) Synthesis of mesoporous chromium phosphates via solid-state reaction at low temperature. New J Chem 36:139–147
Xu L, Wang Z, Song H, Chou L (2013) Catalytic dehydrogenation of isobutane over ordered mesoporous Cr2O3–Al2O3 composite oxides. Catal Commun 35:76–81
Raja R, Thomas JM, Xu M, Harris KD, Greenhill-Hooper M, Quill K (2006) Highly efficient one-step conversion of cyclohexane to adipic acid using single-site heterogeneous catalysts. Chem Commun 4:448–450
Shibuya M, Sato T, Tomizawa M, Iwabuchi Y (2009) Oxoammonium salt/NaClO2: an expedient, catalytic system for one-pot oxidation of primary alcohols to carboxylic acids with broad substrate applicability. Chem Commun 13:1739–1741
Schmidt AK, Stark CB (2011) TPAP-catalyzed direct oxidation of primary alcohols to carboxylic acids through stabilized aldehyde hydrates. Org Lett 13:4164–4167
Wang L, Li J, Dai W, Lv Y, Zhang Y, Gao S (2014) Facile and efficient gold-catalyzed aerobic oxidative esterification of activated alcohols. Green Chem 16:2164–2173
Zhou L, Yu W, Wu L, Liu Z, Chen H, Yang X, Su Y, Xu J (2013) Nanocrystalline gold supported on NaY as catalyst for the direct oxidation of primary alcohol to carboxylic acid with molecular oxygen in water. Appl Catal A 451:137–143
Gao L, Deng K, Zheng J, Liu B, Zhang Z (2015) Efficient oxidation of biomass derived 5-hydroxymethylfurfural into 2,5-furandicarboxylic acid catalyzed by Merrifield resin supported cobalt porphyrin. Chem Eng J 270:444–449
Acknowledgements
The authors sincerely acknowledge the financial support from the Natural Science Foundation of China (21373244, 21576158 and 21576159), Shandong Provincial Natural Science Foundation (2015ZRB0176).
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Miao, Z., Zhou, J., Li, Z. et al. Ordered mesoporous chromium–zirconium oxophosphate composites with homogeneously dispersed chromium oxide: synthesis, characterization and application in liquid phase oxidation of benzyl alcohol and ethylbenzene. J Mater Sci 52, 12141–12155 (2017). https://doi.org/10.1007/s10853-017-1387-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10853-017-1387-9