Page Header

Home > Vol 16, No 2 (Apr.–Jun. 2023) > Trikittiwong

Efficient Oxidation of Benzyl Alcohol to Benzaldehyde with Hydrogen Peroxide Mediated by Palladium Chloride Impregnated on Aluminium Oxide-Pillared Clay

Piyarat Trikittiwong, Danainat Surakiet, Nutthaya Aksornkovit, Kittichai Chaiseeda, Ritbey Ruga, Manuela Stan

Abstract


Aldehydes, such as benzaldehyde, are very important in many industries and can be prepared from alcohols. In this research, aluminium oxide-pillared bentonite (Al-PILC) was prepared by inserting aluminium (III) chloride into the interlayers and calcination. Then PdCl2 was impregnated into Al-PILC and calcined to produce Pd/Al-PILC. The synthesized clay and raw clay were characterized by X-ray diffraction (XRD) and N2 adsorption-desorption (Brunauer-Emmett-Teller; BET) techniques. From the characterization, XRD pattern exhibited the characteristic peaks of montmorillonite at 2θ of 7° and 22°. Additionally, the N2 adsorption-desorption isotherm of Pd/Al-PILC indicated mesoporous structure and BET specific surface area was 102 m2/g. The catalytic activity of Pd/Al-PILC was investigated for the oxidation of benzyl alcohol with H2O2 furnishing benzaldehyde. In the optimum condition, 82% of benzaldehyde was produced via the reaction of benzyl alcohol and H2O2 in the presence of a catalytic amount of Pd/Al-PILC in refluxing acetonitrile for 3 h under mild reaction conditions.

Keywords



[1] R. Naik, A. Nizam, A. Siddekha, and M. A. Pasha, “An efficient sonochemical oxidation of benzyl alcohols into benzaldehydes by FeCl3/HNO3 in acetone,” Ultrasonics Sonochemistry, vol. 18, no. 5, pp. 1124–1127, 2011.

[2] F. Brühne and E. Wright, “Benzaldehyde,” in Ullmann’s Encyclopedia of Industrial Chemistry. New Jersey: Wiley, 2011.

[3] S. F. R. Taylor, J. Sá, and C. Hardacre, “Friedel– Crafts alkylation of aromatics with benzyl alcohol over gold-modified silica,” ChemCatChem, vol. 3, no. 1, pp. 119–121, 2011.

[4] W. J. Zhao and X. Z. Jiang, “Efficient synthesis of benzaldehyde by direct carbonylation of benzene in ionic liquids,” Catalysis Letters, vol. 107, no. 1, pp. 123–125, 2006.

[5] P. J. Figiel, A. M. Kirillov, Y. Y. Karabach, M. N. Kopylovich, and A. J. L. Pombeiro, “Mild aerobic oxidation of benzyl alcohols to benzaldehydes in water catalyzed by aqua-soluble multicopper(II) triethanolaminate compounds,” Journal of Molecular Catalysis A: Chemical, vol. 305, no. 1, pp. 178–182, 2009.

[6] K. Fujita, S. Furukawa, and R. Yamaguchi, “Oxidation of primary and secondary alcohols catalyzed by a pentamethylcyclopentadienyliridium complex,” Journal of Organometallic Chemistry, vol. 649, no. 2, pp. 289–292, 2002.

[7] S. Campestrini, M. Carraro, R. Ciriminna, M. Pagliaro, and U. Tonellato, “Alcohols oxidation with hydrogen peroxide promoted by TPAP-doped ormosils,” Tetrahedron Letters, vol. 45, no. 39, pp. 7283–7286, 2004.

[8] L. Jia, S. Zhang, F. Gu, Y. Ping, X. Guo, Z. Zhong, and F. Su, “Highly selective gas-phase oxidation of benzyl alcohol to benzaldehyde over silvercontaining hexagonal mesoporous silica,” Microporous and Mesoporous Materials, vol. 149, no. 1, pp. 158–165, 2012.

[9] V. Mahdavi and H. R. Hasheminasab, “Vanadium phosphorus oxide catalyst promoted by cobalt doping for mild oxidation of benzyl alcohol to benzaldehyde in the liquid phase,” Applied Catalysis A: General, vol. 482, pp. 189–197, 2014.

[10] W. Partenheimer, “The high yield synthesis of benzaldehydes from benzylic alcohols using homogeneously catalyzed aerobic oxidation in acetic acid,” Advanced Synthesis & Catalysis, vol. 348, no. 4–5, pp. 559–568, 2006.

[11] Y. Zhao, C. Yu, S. Wu, W. Zhang, W. Xue, and Z. Zeng, “Synthesis of benzaldehyde and benzoic acid by selective oxidation of benzyl alcohol with iron(III) tosylate and hydrogen peroxide: A solvent-controlled reaction,” Catalysis Letters, vol. 148, no. 10, pp. 3082–3092, 2018.

[12] C. Zhou, J. Hu, Y. Wang, C. Yao, P. Chakraborty, H. Li, C. Guan, M.-H. Huang, and K.-W. Huang, “Selective carbonylation of benzene to benzaldehyde using a phosphorus–nitrogen PN3P–rhodium(I) complex,” Organic Chemistry Frontiers, vol. 6, no. 6, pp. 721–724, 2019.

[13] W. J. Zhao, X. Z. Jiang, and G. L. Zhuo, “Selective carbonylation of benzene to benzaldehyde using O2 as the oxidant in the presence of cobalt complex,” Journal of Molecular Catalysis A: Chemical, vol. 225, no. 1, pp. 131–135, 2005.

[14] M. L. Chevallier, S. Dessolin, F. Serres, L. Bruyas, and G. Chatel, “Effect of ultrasound on the green selective oxidation of benzyl alcohol to benzaldehyde,” Molecules, vol. 24, no. 22, 2019, Art. no. 4157.

[15] S. Xu, J. Wu, P. Huang, C. Lao, H. Lai, Y. Wang, Z. Wang, G. Zhong, X. Fu, and F. Peng, “Selective catalytic oxidation of benzyl alcohol to benzaldehyde by nitrates,” Frontiers in Chemistry, vol. 8, pp. 1–11, 2020.

[16] L. Chareonsiriwat and W. Chavasiri, “Convenient method for the transformation of epoxide to aldehyde and acetonide mediated by Cr-PLM,” Synthetic Communications, vol. 47, no. 4, pp. 257–267, 2017.

[17] K. Vellayan, B. González, R. Trujillano, M. A. Vicente, and A. Gil, “Pd supported on Cu-doped Ti-pillared montmorillonite as catalyst for the Ullmann coupling reaction,” Applied Clay Science, vol. 160, pp. 126–131, 2018.

[18] K. Sravanthi, D. Ayodhya, and P. Y. Swamy, “Green synthesis, characterization and catalytic activity of 4-nitrophenol reduction and formation of benzimidazoles using bentonite supported zero valent iron nanoparticles,” Materials Science for Energy Technologies, vol. 2, no. 2, pp. 298–307, 2019.

[19] P. Trikittiwong and J. Maliwong, “Synthesis of palladium chloride impregnated on Al2O3- pillared clay for reduction of nitrobenzene,” Key Engineering Materials, vol. 856, pp. 218–223, 2020.

[20] A. Kabadagi, S. Chikkamath, S. Kobayashi, and J. Manjanna, “Organo-modified Fe-montmorillonite as a solid acid catalyst for reduction of nitroarenes and Biginelli reactions,” Applied Clay Science, vol. 189, 2020, Art. no. 105518.

[21] Y. S. Kurniawan, A. C. Imawan, Y. M. Stansyah, and T. D. Wahyuningsih, “Application of activated bentonite impregnated with PdO as green catalyst for acylation reaction of aromatic compounds,” Journal of Environmental Chemical Engineering, vol. 9, no. 4, 2021, Art. no. 105508.

[22] K. R. Jekkidi and S. Navath, “SnCl2/Montmorillonite KSF is an highly efficient heterogeneous reusable catalyst for the selective alkylation of indoles with α, β unsaturated carbonyl compounds under solvent free conditions,” Journal of Molecular Catalysis & Organic Synthesis, vol. 1, pp. 1–4, 2021.

[23] U. Gupta, R. Krishnapriya, and R. K. Sharma, “A sustainable palladium-intercalated montmorillonite clay catalytic system for imine hydrogenation under mild conditions,” ChemPlusChem, vol. 86, no. 4, pp. 540–548, 2021.

[24] M. M. Hashemi, B. Khalili, and B. Eftekhari-sis, “Oxidation of benzylic alcohols to carbonyl compounds with hydrogen peroxide catalysed by manganeses chloride supported on montmorillonite K10,” Journal of Chemical Research, vol. 2005, no. 8, pp. 484–485, 2005.

[25] N. T. Thao, N. T. Nhu, and K.-S. Lin, “Liquid phase oxidation of benzyl alcohol to benzaldehyde over sepiolite loaded chromium oxide catalysts,” Journal of the Taiwan Institute of Chemical Engineers, vol. 83, pp. 10–22, 2018.

[26] X. J. Zhang, H. Song, X. F. Guo, and L. H. Jia, “Catalytic oxidation of benzyl alcohol to benzaldehyde with Fe/Cu-cross-linked montmorillonite,” Advanced Materials Research, vol. 396–398, pp. 1891–1894, 2012.

[27] D. Wang, A. B. Weinstein, P. B. White, and S. S. Stahl, “Ligand-promoted palladiumcatalyzed aerobic oxidation reactions,” Chemical Reviews (Washington, DC, United States), vol. 118, no. 5, pp. 2636–2679, 2018.

[28] J. Ding, Z. Liu, X. Liu, B. Liu, J. Liu, Y. Deng, X. Han, W. Hu, and C. Zhong, “Tunable periodically ordered mesoporosity in palladium membranes enables exceptional enhancement of intrinsic electrocatalytic activity for formic acid oxidation,” Angewandte Chemie International Edition, vol. 59, no. 13, pp. 5092–5101, 2020.

[29] D.-H. Park, J.-H. Yang, A. Vinu, A. Elzatahry, and J.-H. Choy, “X-ray diffraction and X-ray absorption spectroscopic analyses for intercalative nanohybrids with low crystallinity,” Arabian Journal of Chemistry, vol. 9, no. 2, pp. 190–205, 2016.

[30] R. S. Hebbar, A. M. Isloor, B. Prabhu, Inamuddin, A. M. Asiri, and A. F. Ismail, “Removal of metal ions and humic acids through polyetherimide membrane with grafted bentonite clay,” Scientific Reports, vol. 8, no. 1, 2018, Art. no. 4665.

[31] P. K. Tandon, Gayatri, S. Sahgal, M. Srivastava, and S. B. Singh, “Catalysis by Ir(III), Rh(III) and Pd(II) metal ions in the oxidation of organic compounds with H2O2,” Applied Organometallic Chemistry, vol. 21, no. 3, pp. 135–138, 2007.

[32] G. Barak, J. Dakka, and Y. Sasson, “Selective oxidation of alcohols by a H2O2-RuCl3 system under phase-transfer conditions,” Journal of Organic Chemistry, vol. 53, no. 15, pp. 3553–3555, 1988.

[33] J. Pritchard, L. Kesavan, M. Piccinini, Q. He, R. Tiruvalam, N. Dimitratos, J. A. Lopez-Sanchez, A. F. Carley, J. K. Edwards, C. J. Kiely, and G. J. Hutchings, “Direct synthesis of hydrogen peroxide and benzyl alcohol oxidation using Au−Pd catalysts prepared by sol immobilization,” Langmuir, vol. 26, no. 21, pp. 16568–16577, 2010.

[34] S. Tareq, Y. H. T. Yap, T. A. Saleh, A. H. Abdullah, U. Rashid, and M. I. Saiman, “Synthesis of bimetallic gold-pallidum loaded on carbon as efficient catalysts for the oxidation of benzyl alcohol into benzaldehyde,” Journal of Molecular Liquids, vol. 271, pp. 885–891, 2018.

[35] A. Kunene, G. Leteba, and E. van Steen, “Liquid phase oxidation of benzyl alcohol over Pt and Pt–Ni alloy supported on TiO2: Using O2 or H2O2 as oxidant?,” Catalysis Letters, vol. 152, pp. 1760–1768, 2021.

Full Text: PDF

DOI: 10.14416/j.asep.2022.08.004

Refbacks

  • There are currently no refbacks.


Copyright © 2024 by King Mongkut’s University of Technology North Bangkok. All rights reserved.