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Catalysis Letters

, Volume 149, Issue 12, pp 3370–3383 | Cite as

Catalytic Role of Pd(II) Ions in Mg–Al Hydrotalcites for the Oxidation of Styrene

  • Nguyen Tien ThaoEmail author
  • Le Thi Kim Huyen
  • Angela Köckritz
Article
  • 65 Downloads

Abstract

Pd(II) ions were introduced into Mg0.7Al0.3(OH)2(CO3)0.15·mH2O through the co-precipitation of the corresponding nitrate salts at a constant pH value. The presence of Pd in the brucite-like layers affects an increased surface area and decreased crystal domain of the Mg–Al hydrotalcite catalysts. Pd(II) ions may exist in both intra- and extra- brucite-like layers and exhibit different roles in the oxidation of styrene with t-BuOOH, depending on the amount of palladium. The insertion of Pd(II) into the hydrotalcite lattice has significantly improved the catalyst stability. The highest conversion of styrene is about 80% for the production of styrene oxide and benzaldehyde at low temperatures.

Graphic Abstract

Keywords

Oxidation Pd-doped hydrotalcite Styrene oxide Benzaldehyde t-BuOOH 

Notes

Acknowledgements

This research is funded by Vietnam National Foundation for Science and Technology Development (NAFOSTED) under Grant No. 104.05-2017.04. We would like to acknowledge the RoHan Project supported by German Academic Exchange Service (DAAD, No. 57315854) and the German Federal Ministry for Economic Cooperation and Development (BMZ) inside the framework “SDG Bilateral Graduate school program”.

Supplementary material

10562_2019_2915_MOESM1_ESM.doc (40 kb)
Supplementary material 1 (DOC 40 kb)

References

  1. 1.
    Dusi M, Malliat T, Baiker A (2000) Epoxidation of functionalized olefins over solid catalysts. Catal Rev 42(1–2):213–278Google Scholar
  2. 2.
    Polyakov M, Schaffner B, Kruse D, Martin A, Knockritz A (2016) Epoxide and cyclic carbonate with diisononyl succinate backbone as phthalate-free plasticizers. Tetrahedron Lett 57:964–968Google Scholar
  3. 3.
    Tien Thao N, Huu Trung H (2014) Selective oxidation of styrene over Mg-Co-Al hydrotalcite like-catalysts using air as oxidant. Catal Commun 45:153–157Google Scholar
  4. 4.
    Liu J, Chen T, Yan X, Wang Z, Jian R, Jian P, Yuan E (2018) NiCo2O4 nanoneedle-assembled hierarchical microflowers for highly selective oxidation of styrene. Catal Commun 109:71–75Google Scholar
  5. 5.
    Muzart J (2011) Pd-catalyzed oxidation of alkynes. J Mol Catal A 338:7–17Google Scholar
  6. 6.
    Noh J-H, Patala R, Meijboom R (2016) Catalytic evaluation of dendrimer and reverse microemulsion template Pd and Pt nanoparticles for the selective oxidation of styrene using TBHP. Appl Catal A 514:253–266Google Scholar
  7. 7.
    Wang F, Zhang J, Liu C, Liu J (2015) Pd–palygorskite catalysts: preparation, characterization and catalytic performance for the oxidation of styrene. Appl Clay Sci 105–106:150–155Google Scholar
  8. 8.
    He X, Chen L, Zhou X, Ji H (2016) Recyclable Pd supported catalysts with low loading for efficient epoxidation of olefins at ambient conditions. Catal Commun 83:78–81Google Scholar
  9. 9.
    Song J, Zhang Z, Jiang T, Hu S, Li W, Xie Y, Han B (2008) Epoxidation of styrene to styrene oxide using carbon dioxide and hydrogen peroxide in ionic liquids. J Mol Catal A 279:235–238Google Scholar
  10. 10.
    Cardoso M, Silva AR, de Castro B, Freire C (2005) Styrene epoxidation catalysed by manganese(III) salen complex supported on activated carbons. Appl Catal A 285:110–118Google Scholar
  11. 11.
    Yu JQ, Corey EJ (2002) Diverse pathways for the palladium(II)-mediated oxidation of olefins bytert-butylhydroperoxide. Org Lett 4(16):2727–2730PubMedGoogle Scholar
  12. 12.
    Liu J, Fang S, Jian R, Wu F, Jian P (2018) Silylated Pd/Ti-MCM-41 catalyst for the selective production of propylene oxide from the oxidation of propylene with cumene hydroperoxide. Powder Technol 329:19–24Google Scholar
  13. 13.
    Wang Q, Wang L, Mi Z (2005) Influence of Pt–Pd/TS-1 catalyst preparation on epoxidation of olefins with hydrogen peroxide. Catal Lett 103:161–164Google Scholar
  14. 14.
    Bussi J, Lopez A, Pena F, Timbal P, Paz D, Lorenzo D, Dellacasa E (2003) Liquid phase oxidation of limonene catalyzed by palladium supported on hydrotalcites. Appl Catal A 253:177–189Google Scholar
  15. 15.
    Ota A, Kunkes EL, Kasatkin I, Groppo E, Ferri D, Poceiro B, Yerga RMN, Behrens M (2012) Comparative study of hydrotalcite-derived supported Pd2Ga and PdZn intermetallic nanoparticles as methanol synthesis and methanol steam reforming catalysts. J Catal 293:27–38Google Scholar
  16. 16.
    Tien Thao N, Kim Huyen LT (2015) Catalytic oxidation of styrene over Cu-doped hydrotalcites. Chem Eng J 279:840–850Google Scholar
  17. 17.
    Bukhtiyarova MV (2019) A review on effect of synthesis conditions on the formation of layered double hydroxides. J Solid State Chem 269:494–506Google Scholar
  18. 18.
    Nishimura S, Takagaki A, Ebitani K (2013) Characterization, synthesis and catalysis of hydrotalcite-related materials for highly efficient materials transformations. Green Chem 15:2026–2042Google Scholar
  19. 19.
    Mora M, Jimenez-Sanchidrian C, Ruiz J (2006) Heterogeneous Suzuki cross-coupling reactions over palladium/hydrotalcite catalysts. J Colloid Interface Sci 302:568–575PubMedGoogle Scholar
  20. 20.
    Li L, Lia G, Yuana Y (2015) Mesoporous PdO/Pt/Al2O3 film produced by reverse-micro-emulsion and its application for methane micro-sensor. RSC Adv 5:4586–4591Google Scholar
  21. 21.
    Barrabes N, Frare A, Föttinger K, Urakawa A, Llorca J, Rupprechter G, Tichit D (2012) Pt-Cu bimetallic catalysts obtained from layered double hydroxides by an anion-exchange route. Appl Clay Sci 69:1–10Google Scholar
  22. 22.
    Christensen GL, Langell MA (2013) Characterization of copper palladium oxide solid solutions by X–ray diffraction, X–ray photoelectron spectroscopy, and Auger electron spectroscopy. J Phys Chem C 117:7039–7049Google Scholar
  23. 23.
    Priolkar KR, Bera P, Sarode PR, Hegde MS, Emura S, Kumashiro R, Lalla NP (2002) Formation of Ce1-xPdxO2-δ Solid solution in combustion-synthesized Pd/CeO2 catalyst: XRD, XPS, and EXAFS investigation. Chem Mater 14:2120–2128Google Scholar
  24. 24.
    Ling F, Anthony OC, Xiong Q, Luo M, Pan X, Jia L, Huang J, Sun D, Li Q (2016) PdO/LaCoO3 heterojunction photocatalysts for highly hydrogen production from formaldehyde aqueous solution under visible light. Int J Hydrogen Energy 41:6115–6122Google Scholar
  25. 25.
    Baylet A, Marecot P, Duprez D, Castellazzi P, Groppi G, Forzatti P (2011) In situ Raman andin situ XRD analysis of PdO reduction and Pdo oxidation supported onc-Al2O3catalyst under different atmospheres. Phys Chem Chem Phys 13:4607–4613PubMedGoogle Scholar
  26. 26.
    Zhao Z, Elwood J, Carpenter MA (2015) Phonon anharmonicity of PdO studied by Raman spectrometry. J Phys Chem C 119:23094–23102Google Scholar
  27. 27.
    Costa VV, da Silva Rocha KA, Kozhevnikov IV, Gusevskaya EV (2010) Isomerization of styrene oxide to phenylacetaldehyde over supported phosphotungstic heteropoly acid. Appl Catal A 383:217–220Google Scholar
  28. 28.
    Zhang F, Zhao X, Feng C, Li B, Chen T, Lu W, Lei X, Sailong Xu (2011) Crystal-face-selective supporting of gold nanoparticles on layered double hydroxide as efficient catalyst for epoxidation of styrene. ACS Catal 1:232–237Google Scholar
  29. 29.
    Patil NS, Uphade BS, Jana P, Bharagava SK, Choudhary VR (2004) Epoxidation of styrene by anhydrous t-butyl hydroperoxide over reusable gold supported on MgO and other alkaline earth oxides. J Catal 223:236–239Google Scholar
  30. 30.
    Adam F, Iqbal A (2011) The liquid phase oxidation of styrene with tungsten modified silica as a catalyst. Chem Eng J 171:1379–1386Google Scholar
  31. 31.
    Feng B, Hou Z, Wang X, Hu Y, Li H, Qiao Y (2009) Selective aerobic oxidation of styrene to benzaldehydecatalyzed by water-soluble palladium(II) complex in water. Green Chem 11:1446–1452Google Scholar
  32. 32.
    Masunga N, Doyle BP, Carleschi E, Meijboom R (2018) Excellent product selectivity towards 2-phenyl-acetaldehyde and styrene oxide using manganese oxide and cobalt oxide NPs for the selective oxidation of styrene. Appl Catal A 559:175–186Google Scholar
  33. 33.
    Tien Thao N, Duc Trung N, Van Long D (2016) Activity of molybdate-intercalated layered double hydroxides in the oxidation of styrene with air. Catal Lett 146(5):918–928Google Scholar
  34. 34.
    Liu J, Chen T, Jian P, Wang L, Yan X (2018) Hollow urchin-like NiO/NiCo2O4 heterostructures as highly efficient catalysts for selective oxidation of styrene. J Colloid Interface Sci 526:295–301PubMedGoogle Scholar
  35. 35.
    Sharma S, Sinha S, Chand S (2012) Polymer anchored catalysts for oxidation of styrene using TBHP and molecular oxygen. Ind Eng Chem Res 51:8806–8814Google Scholar
  36. 36.
    Tien Thao NT, Kim Huyen LT (2019) Enhanced catalytic performance of Cr-inserted hydrotalcites in the liquid oxidation of styrene. J Ind Eng Chem 73:221–232Google Scholar
  37. 37.
    Gu B, Bai J, Yang W, Li Chunping (2019) Synthesis of ANA-zeolite-based Cu nanoparticles composite catalyst and its regularity in styrene oxidation. Microporous Mesoporous Mater 274:318–326Google Scholar
  38. 38.
    Liu C, Huang J, Sun D, Zhou Y, Jing X, Du M, Wang H, Li Q (2013) Anatase type extra-framework titanium in TS-1: a vital factor influencing the catalytic activity toward styrene epoxidation. Appl Catal A 459:1–7Google Scholar
  39. 39.
    Wang X, Zhang X, Wang Y, Liu H, Qiu J, Wang J, Han W, Yeung KL (2011) Performance of TS-1-coated structured packing materials for styrene oxidation reaction. ACS Catal 1:437–445Google Scholar
  40. 40.
    Valand J, Parekh H, Friedrich HB (2013) Mixed Cu–Ni–Co nano-metal oxides: a new class of catalysts for styrene oxidation. Catal Commun 40:149–153Google Scholar
  41. 41.
    Wang G, Zhang S, Huang Y, Kang F, Yang Z, Guo Y (2012) Styrene epoxidation over V-SBA-15 with alkaline-earth metal ion promotion under photo-assisted conditions. Appl Catal A 413–414:52–61Google Scholar
  42. 42.
    Prasad Neeli CK, Narani A, Marella RK, Rao KSR, Burri DR (2013) Selective benzyl oxidation of alkylaromatics over Cu/SBA-15 catalysts under solvent-free conditions. Catal Commun 39:5–9Google Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Nguyen Tien Thao
    • 1
    Email author
  • Le Thi Kim Huyen
    • 1
  • Angela Köckritz
    • 2
  1. 1.Faculty of ChemistryVietnam National University, HanoiHanoiVietnam
  2. 2.Leibniz Institute for Catalysis (LIKAT Rostock)RostockGermany

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