Propylamine Silica-Titania Hybrid Material Modified with Ni(II) as the Catalyst for Benzyl Alcohol to Benzaldehyde Conversion

Dewi Agustiningsih; Nuryono Nuryono; Sri Juari Santosa; Eko Sri Kunarti

doi:10.22146/ijc.84282

Propylamine Silica-Titania Hybrid Material Modified with Ni(II) as the Catalyst for Benzyl Alcohol to Benzaldehyde Conversion

https://doi.org/10.22146/ijc.84282

Dewi Agustiningsih⁽¹⁾, Nuryono Nuryono⁽²⁾, Sri Juari Santosa⁽³⁾, Eko Sri Kunarti^(4*)

(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281, Indonesia
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281, Indonesia
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281, Indonesia
(4) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281, Indonesia
(*) Corresponding Author

Abstract

SiO₂-TiO₂@propylamine-Ni(II) as the catalyst for the benzyl alcohol oxidation has been synthesized by utilizing rice husk ash as the SiO₂ source. This research was started by extracting SiO₂ from rice husk ash and continued by synthesizing the SiO₂-TiO₂ composite using titanium(IV) tetraisopropoxide (TTIP) as TiO₂ precursor and PEG-40 as template. The composite functionalization and metal modification were carried out by adding (3-aminopropyl)triethoxysilane (APTES) as the source of propylamine linker and impregnating NiCl₂·6H₂O as the nickel precursor, respectively. The catalysts were synthesized by varying the ratios between each component within the material. The prepared materials were then characterized using ATR-IR, XRD, XRF, PSA, SAA, AAS, SEM-EDX, HR-TEM, and TGA. The catalyst activity was investigated by applying it to the oxidation reaction of benzyl alcohol to benzaldehyde with H₂O₂ as the oxidizing agent under sonication system. The obtained products were then analyzed by using GC-MS to quantify the success of the reaction. All characterizations performed in this research generally indicate the success in the synthesis of SiO₂-TiO₂@propylamine-Ni(II) materials. Under the same condition including at room temperature, 1 h reaction time, and sonication system, the optimal oxidation reaction of benzyl alcohol was reached when SiO₂-TiO₂@propylamine-Ni(II)5 was used as the catalyst in 98.52% yield.

Keywords

benzaldehyde; benzyl alcohol; catalyst; oxidation reaction; SiO2-TiO2@propylamine-Ni(II)

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References

[1] Kunene, A., Leteba, G., and van Steen, E., 2022, Liquid phase oxidation of benzyl alcohol over Pt and Pt–Ni alloy supported on TiO₂: Using O₂ or H₂O₂ as oxidant?, Catal. Lett., 152 (6), 1760–1768.

[2] Javidfar, F., Fadaeian, M., and Ghomi, J.S., 2021, La(OH)₃ nanoparticles immobilized on Fe₃O₄@chitosan composites as novel magnetic nanocatalysts for sonochemical oxidation of benzyl alcohol to benzaldehyde, RSC Adv., 11 (57), 35988–35993.

[3] Ramesh, A., Da, C.T., Manigandan, R., Bhargav, P.B., and Nguyen-Le, M.T., 2022, Selectivity oxidation of benzyl alcohol using mesoporous g-C₃N₄ catalysts prepared by hard template method, Colloid Interface Sci. Commun., 48, 100608.

[4] Vásquez-Céspedes, S., Betori, R.C., Cismesia, M.A., Kirsch, J.K., and Yang, Q., 2021, Heterogeneous catalysis for cross-coupling reactions: An underutilized powerful and sustainable tool in the fine chemical industry?, Org. Process Res. Dev., 25 (4), 740–753.

[5] Lima, M.J., Tavares, P.B., Silva, A.M.T., Silva, C.G., and Faria, J.L., 2017, Selective photocatalytic oxidation of benzyl alcohol to benzaldehyde by using metal-loaded g-C₃N₄ photocatalysts, Catal. Today, 287, 70–77.

[6] Wu, P., Cao, Y., Zhao, L., Wang, Y., He, Z., Xing, W., Bai, P., Mintova, S., and Yan, Z., 2019, Formation of PdO on Au–Pd bimetallic catalysts and the effect on benzyl alcohol oxidation, J. Catal., 375, 32–43.

[7] Wang, Y., Hu, D., Guo, R., Deng, H., Amer, M., Zhao, Z., Xu, H., and Yan, K., 2022, Facile synthesis of Ni/Fe₃O₄ derived from layered double hydroxides with high performance in the selective hydrogenation of benzaldehyde and furfural, Mol. Catal., 528, 112505.

[8] Hu, X., Zhang, M., Ren, A., Huang, Y., Yan, X., Feng, R., and Zhao, G., 2022, Mesoporous nickel-cobalt oxide for efficient liquid-phase benzyl alcohol oxidation by air, Catal. Today, 405-406, 75–81.

[9] Cui, C., Zhao, X., Su, X., Gao, W., Zhan, J., Zhang, X., Li, G., Zhang, X. L., Sang, Y., and Liu, H., 2021, Selective oxidation of benzyl alcohol using a Ni(OH)₂-modified CdS-MoS₂ composite photocatalyst under ambient conditions, J. Environ. Chem. Eng., 9 (6), 106416.

[10] Ali, M.E., Rahman, M.M., Sarkar, S.M., and Abd Hamid, S.B., 2014, Heterogeneous metal catalysts for oxidation reactions, J. Nanomater., 2014, 192038.

[11] Bagheri, S., Muhd Julkapli, N., and Bee Abd Hamid, S., 2014, Titanium dioxide as a catalyst support in heterogeneous catalysis, Sci. World J., 2014, 727496.

[12] Deshmukh, P., Bhatt, J., Peshwe, D., and Pathak, S., 2012, Determination of silica activity index and XRD, SEM and EDS studies of amorphous SiO₂ extracted from rice husk ash, Trans. Indian Inst. Met., 65 (1), 63–70.

[13] Setyawan, N., Hoerudin, H., and Yuliani, S., 2021, Synthesis of silica from rice husk by sol-gel method, IOP Conf. Ser.: Earth Environ. Sci., 733, 012149.

[14] Muthukrishnan, S., Gupta, S., and Kua, H.W., 2019, Application of rice husk biochar and thermally treated low silica rice husk ash to improve physical properties of cement mortar, Theor. Appl. Fract. Mech., 104, 102376.

[15] Ozturk, M., Karaaslan, M., Akgol, O., and Sevim, U.K., 2020, Mechanical and electromagnetic performance of cement based composites containing different replacement levels of ground granulated blast furnace slag, fly ash, silica fume and rice husk ash, Cem. Concr. Res., 136, 106177.

[16] Santhosh, K.G., Subhani, S.M., and Bahurudeen, A., 2022, Recycling of palm oil fuel ash and rice husk ash in the cleaner production of concrete, J. Cleaner Prod., 354, 131736.

[17] Avudaiappan, S., Prakatanoju, S., Amran, M., Aepuru, R., Saavedra Flores, E.I., Das, R., Gupta, R., Fediuk, R., and Vatin, N., 2021, Experimental investigation and image processing to predict the properties of concrete with the addition of nano silica and rice husk ash, Crystals, 11 (10), 1230.

[18] Qureshi, L.A., Ali, B., and Ali, A., 2020, Combined effects of supplementary cementitious materials (silica fume, GGBS, fly ash and rice husk ash) and steel fiber on the hardened properties of recycled aggregate concrete, Constr. Build. Mater., 263, 120636.

[19] Saloni, S., Parveen, P., and Pham, T.M., 2020, Enhanced properties of high-silica rice husk ash-based geopolymer paste by incorporating basalt fibers, Constr. Build. Mater., 245, 118422.

[20] Hossain, S.S., Roy, P.K., and Bae, C.J., 2021, Utilization of waste rice husk ash for sustainable geopolymer: A review, Constr. Build. Mater., 310, 125218.

[21] Liang, G., Zhu, H., Li, H., Liu, T., and Guo, H., 2021, Comparative study on the effects of rice husk ash and silica fume on the freezing resistance of metakaolin-based geopolymer, Constr. Build. Mater., 293, 123486.

[22] Nana, A., Epey, N., Rodrique, K.C., Deutou, J.G.N., Djobo, J.N.Y., Tomé, S., Alomayri, T.S., Ngouné, J., Kamseu, E., and Leonelli, C., 2021, Mechanical strength and microstructure of metakaolin/volcanic ash-based geopolymer composites reinforced with reactive silica from rice husk ash (RHA), Materialia, 16, 101083.

[23] Handayani, L., Aprilia, S., Abdullah, A., Rahmawati, C., Aulia, T.B., Ludvig, P., and Ahmad, J., 2022, Sodium silicate from rice husk ash and their effects as geopolymer cement, Polymers, 14 (14), 2920.

[24] Steven, S., Restiawaty, E., Pasymi, P., and Bindar, Y., 2021, An appropriate acid leaching sequence in rice husk ash extraction to enhance the produced green silica quality for sustainable industrial silica gel purpose, J. Taiwan Inst. Chem. Eng., 122, 51–57.

[25] Nayak, P.P., and Datta, A.K., 2021, Synthesis of SiO₂-nanoparticles from rice husk ash and its comparison with commercial amorphous silica through material characterization, Silicon, 13 (4), 1209–1214.

[26] Zainal, N.S., Mohamad, Z., Mustapa, M.S., Badarulzaman, N.A., and Zulkifli, A.Z., 2019, The ability of crystalline and amorphous silica from rice husk ash to perform quality hardness for ceramic water filtration membrane, Int. J. Integr. Eng., 11 (5), 229–235.

[27] Fatimah, I., Said, A., and Hasanah, U.A., 2015, Preparation of TiO₂-SiO₂ using rice husk ash as silica source and the kinetics study as photocatalyst in methyl violet decolorization, Bull. Chem. React. Eng. Catal., 10 (1), 43–49.

[28] Prabha, S., Durgalakshmi, D., Rajendran, S., and Lichtfouse, E., 2021, Plant-derived silica nanoparticles and composites for biosensors, bioimaging, drug delivery and supercapacitors: A review, Environ. Chem. Lett., 19 (2), 1667–1691.

[29] Jamwal, B., Kaur, M., Sharma, H., Khajuria, C., Paul, S., and Clark, J.H., 2019, Diamines as interparticle linkers for silica-titania supported PdCu bimetallic nanoparticles in Chan-Lam and Suzuki cross-coupling reactions, New J. Chem., 43 (12), 4919–4928.

[30] Mardjan, M.I.D., Hariadi, M.F., Putri, I.M., Musyarrofah, N.A., Salimah, M., Priatmoko, P., Purwono, B., and Commeiras, L., 2022, Ultrasonic-assisted-synthesis of isoindolin-1-one derivatives, RSC Adv., 12 (29), 19016–19021.

[31] Bai, Y., Li, Z., Cheng, B., Zhang, M., and Su, K., 2017, Higher UV-shielding ability and lower photocatalytic activity of TiO₂@SiO₂/APTES and its excellent performance in enhancing the photostability of poly(p-phenylene sulfide), RSC Adv., 7 (35), 21758–21767.

[32] Harraz, F.A., 2008, Polyethylene glycol-assisted hydrothermal growth of magnetite nanowires: Synthesis and magnetic properties, Phys. E, 40 (10), 3131–3136.

[33] Kumar, P., Khanduri, H., Pathak, S., Singh, A., Singh, A., Basheed, G.A., and Pant, R.P., 2020, Temperature selectivity for single phase hydrothermal synthesis of PEG-400 coated magnetite nanoparticles, Dalton Trans., 49 (25), 8672–8683.

[34] Netzahual-Lopantzi, Á., Sánchez-Ramírez, J.F., Jiménez-Pérez, J.L., Cornejo-Monroy, D., López-Gamboa, G., and Correa-Pacheco, Z.N., 2019, Study of the thermal diffusivity of nanofluids containing SiO₂ decorated with Au nanoparticles by thermal lens spectroscopy, Appl. Phys. A, 125 (9), 588.

[35] Eslami, S., Farhangdoost, B., Shahverdi, H., and Mohammadi, M., 2021, Surface grafting of silica nanoparticles using 3-aminopropyl (triethoxysilane) to improve the CO₂ absorption and enhance the gas consumption during the CO₂ hydrate formation, Greenhouse Gases: Sci. Technol., 11 (5), 939–953.

[36] Roe, S.P., Hill, J.O., and Magee, R.J., 1991, An infrared and electronic spectroscopic study of a series of nickel(II) amine complexes, Monatsh. Chem., 122 (6), 467–478.

[37] Ning, X., Lu, Y., Fu, H., Wan, H., Xu, Z., and Zheng, S., 2017, Template-mediated Ni(II) dispersion in mesoporous SiO₂ for preparation of highly dispersed Ni catalysts: Influence of template type, ACS Appl. Mater. Interfaces, 9 (22), 19335–19344.

[38] Tian, Y., Jiao, W., Liu, P., Song, S., Lu, Z., Hirata, A., and Chen, M., 2019, Fast coalescence of metallic glass nanoparticles, Nat. Commun., 10 (1), 5249.

[39] Haghighi, M., and Gooneh-Farahani, S., 2020, Insights to the oxidative desulfurization process of fossil fuels over organic and inorganic heterogeneous catalysts: Advantages and issues, Environ. Sci. Pollut. Res., 27 (32), 39923–39945.

[40] Babyszko, A., Wanag, A., Sadłowski, M., Kusiak-Nejman, E., and Morawski, A.W., 2022, Synthesis and characterization of SiO₂/TiO₂ as photocatalyst on methylene blue degradation, Catalysts, 12 (11), 1372.

[41] Wang, L.H., Kong, F.Y., and Tai, X.S., 2022, Synthesis, structural characterization of a new Ni(II) complex and its catalytic activity for oxidation of benzyl alcohol, Bull. Chem. React. Eng. Catal., 17 (2), 375–382.

[42] Bao, X., Li, H., Wang, Z., Tong, F., Liu, M., Zheng, Z., Wang, P., Cheng, H., Liu, Y., Dai, Y., Fan, Y., Li, Z., and Huang, B., 2021, TiO₂/Ti₃C₂ as an efficient photocatalyst for selective oxidation of benzyl alcohol to benzaldehyde, Appl. Catal., B, 286, 119885.

[43] Qayyum, A., Giannakoudakis, D.A., LaGrow, A.P., Bondarchuk, O., Łomot, D., and Colmenares, J.C., 2022, High-frequency sonication for the synthesis of nanocluster-decorated titania nanorods: Making a better photocatalyst for the selective oxidation of monoaromatic alcohol, Catal. Commun., 163, 106406.

[44] Hikmah, N., Agustiningsih, D., Nuryono, N., and Kunarti, E.S., 2022, Preparation of iron-doped SiO₂/TiO₂ using silica from sugarcane bagasse ash for visible light degradation of Congo Red, Indones, J. Chem., 22 (2), 402–412.

DOI: https://doi.org/10.22146/ijc.84282