Abstract
Nano 12-tungtophosphoric acid cesium salt (Cs-TPA) was synthesized under ultrasonic irradiation in nanoscale. The obtained catalyst was characterized by various methods. These analyzes indicate that the chemical structure and crystallinity of nano Cs-TPA remained unchanged while its morphology was found to be different from traditional Cs-TPA which is in irregular shape, becoming spherical with an average particle size of about 50 nm.
Nano Cs-TPA was examined in the alkylation of benzene with dec-1-ene, its catalytic activity was remarkably enhanced compared to its original state. The catalyst reusability experiment also showed that the activity of nano Cs-TPA does not decrease even after five reused cycles.
Funding statement: The authors thank Anadolu University Scientific Research Projects Commission (Project No:1207F112) for the financial support.
References
[1] A.R. Abbasi, A. Morsali, Ultrasound-assisted coating of silk yarn with silver chloride nanoparticles, Colloids Surf. A, 371 (1–3) (2010) 113–118.10.1016/j.colsurfa.2010.09.014Search in Google Scholar
[2] S.V. Awate, S. B. Waghmode, M.S., Synthesis. characterization and catalytic evaluation of zirconia-pillared montmorillonite for linear alkylation of benzene, Agashe, Catal. Commun. 5 (2004) 407–411.10.1016/j.catcom.2004.04.005Search in Google Scholar
[3] J.L. Berna, L. Cavalli, C. Renta, European Life-Cycle Inventory for Detergent Surfactants Production, Tenside Surfact Det. 32 (1995) 122.10.1515/tsd-1995-320209Search in Google Scholar
[4] L.E. Briand. G.T. Baronelti. H.J. Thomas, The state of the art on Wells–Dawson heteropoly-compounds: A review of their properties and applications, Appl. Catal. A Gen. 256 (2003) 37–50.10.1016/S0926-860X(03)00387-9Search in Google Scholar
[5] Cai. X.. Cui. S.. Qu. L.. Yuan. D.. Lu. B.. and Cai. Q., Alkylation of benzene and dichloromethane to diphenylmethane with acidic ionic liquids, Catal. Comm., 9(2008), 1173–1177.10.1016/j.catcom.2007.10.029Search in Google Scholar
[6] X. Chen, Z. Xu, T. Okuhara, Liquid phase esterification of acrylic acid with 1-butanol catalyzed by solid acid catalysts, Appl. Catal. A Gen., 180 (1999) 261–269.10.1016/S0926-860X(98)00337-8Search in Google Scholar
[7] S. W. Chuang, S. L. C. Hsu, M. L. Yang, Preparation and characterization of fluorine-containing polybenzimidazole/imidazole hybrid membranes for proton exchange membrane fuel cells, Eur. Polym. J. 44 (2008) 2202–2206.10.1016/j.eurpolymj.2008.04.021Search in Google Scholar
[8] L. Cohen, R. Vergara, A. Moreno, J. L. Berna, Influence of 2-Phenyl Alkane and Tetralin Content on Solubility and Viscosity of Linear Alkylbenzene Sulfonate, J. Am. Oil Chem. Soc. 72 (1995) 115–122.10.1007/BF02635788Search in Google Scholar
[9] I. Craciun.M.F. Reyniers, G.B. Marin, Effects of acid properties of Y zeolites on the liquid-phase alkylation of benzene with 1-octene: A reaction path analysis, J. Mol. Catal. A Chem. 277(2007). 1–14.10.1016/j.molcata.2007.06.027Search in Google Scholar
[10] Z. Da. P. Magnoux. M. Guisnet, Alkylation of toluene with 1‐dodecene over HFAU zeolite. Deactivation and regeneration, Catal. Lett. 61 (1999) 203–206.10.1023/A:1019024922650Search in Google Scholar
[11] E. Ödeş Akbay, G. Demir, A Comparative Study on Characterization of 12-Tungstophosphoric Acid Cesium Salt Depending on Synthesis Methods, Asian J. Chem. 26(18) (2014) 6061–606610.14233/ajchem.2014.16667Search in Google Scholar
[12] N. Essayem, G. Couudurier, M. Fourier, J.C. Vedrine, Acidic and catalytic properties of CsxH3−xPW12O40 heteropolyacid compounds,Catal. Lett. 34 (1995) 223–235.10.1007/BF00808337Search in Google Scholar
[13] H. Faghihian, M.H. Mohammadi, Acid activation effect on the catalytic performance of Al-pillared bentonite in alkylation of benzene with olefins, Appl. Clay Sci. 93–94 (2014) 1–7Search in Google Scholar
[14] R.M. Fernandes. E.R. Lachter. Evaluation of sulfonic resins for liquid phase alkylation of toluene, Catal. Commun. 6 (2005) 550–55410.1016/j.catcom.2005.04.022Search in Google Scholar
[15] S.R. Guerra. L.M.O.C. Merat. R.A.S. San Gil. L.C. Dieguez, Alkylation of benzene with olefins in the presence of zirconium-pillared clays, Catal. Today, 133–135 (2008) 223–230.10.1016/j.cattod.2007.12.094Search in Google Scholar
[16] A. Hafizi, A. Ahmadpour, M. M. Heravi, F. F. Bamoharram, The Application of Silica-Supported Preyssler HPA as a Heterogeneous and Green Catalyst for the Alkylation of Benzene, Pet. Sci. Technol. 32(9) (2014) 1022–1027.10.1080/10916466.2011.637534Search in Google Scholar
[17] M. M. Heravi, M. Khorasani, F. Derikvand, H.A. Oskooie, F. F. Bamoharram, Highly efficient synthesis of coumarin derivatives in the presence of H14[NaP5W30O110] as a green and reusable catalyst, Catal. Commun. 8 (2007) 1886–1890.10.1016/j.catcom.2007.02.030Search in Google Scholar
[18] J. G. Hern´ andez-Cortez, L. Martinez, L. Soto, A. L´ opez, J. Navarrete, M. Manr´ıquez. V. H. Lara, E. L. Salinas, Liquid phase alkylation of benzene with dec-1-ene catalyzed on supported 12-tungstophosphoric acid, Catal. Today 150 (2010) 346–352.10.1016/j.cattod.2009.12.003Search in Google Scholar
[19] J.G. Herna´ndez-Cortez, L. Martinez, L. Soto, A.Lo´pez, J. Navarrete, Ma. Manrı´quez, V.H. Lara, E.Lo´pez-Salinas, Liquid phase alkylation of benzene with dec-1-ene catalyzed on supported 12-tungstophosphoric acid, Catal. Today 150 (2010) 346–35210.1016/j.cattod.2009.12.003Search in Google Scholar
[20] Kim, J. K.; Park, H. W.; Hong, U. G.; Choi, J. H.; Song, I. K., CsxH3.0 - xPW12O40 (X = 2.0-3.0) Heteropolyacid Nano-Catalysts for Catalytic Decomposition of 2,3-Dihydrobenzofuranto Aromatics, J. of Nanoscience and Nanotechnology, 14(11), 2014, 8884–8890.10.1166/jnn.2014.9947Search in Google Scholar
[21] E.R. Lachter, R.A.S. San Gil, D. Tabak, V.G. Costa, C.P.S. Chaves, J.A. Santos, Alkylation of toluene with aliphatic alcohols and 1-octene catalyzed by cation-exchange resins, Reac. Funct. Polym. 44 (2000) 1–7.10.1016/S1381-5148(99)00071-1Search in Google Scholar
[22] Y. Liu, L. Xu, B. Xu, Z.Li, L. Jia, W. Guo, Toluene alkylation with 1-octene over supported heteropoly acids on MCM-41 catalysts, J. Mol. Catal. A: Chem. 297 (2009) 86–9210.1016/j.molcata.2008.09.007Search in Google Scholar
[23] M. Martos. J. Morales. L. Sanchez. R. Ayouchi. D. Leinen. F. Martin. J.R. Ramos Barrado. Electrochemical properties of lead oxide films obtained by spray pyrolysis as negative electrodes for lithium secondary batteries, Electrochim. Acta 46 (2001) 2939–2948.10.1016/S0013-4686(01)00512-6Search in Google Scholar
[24] K. Na. T. Okuhara. M. Misono, Skeletal isomerization of n-butane over caesium hydrogen salts of 12-tungstophosphoric acid, J. Chem. Soc. Faraday. Trans. 91 (1995) 367–373.10.1039/ft9959100367Search in Google Scholar
[25] T. Nakato, Y. Toyoshi, M. Kimura, T. Okuhara, Unique catalysis of an acidic salt of heteropoly acid, Cs2.5H0.5PW12O40, consisting of microcrystallites, Catal. Today 52 (1999) 23–28.10.1016/S0920-5861(99)00059-0Search in Google Scholar
[26] T. Okuhara, H. Watanabe, T. Nishiruma, K. Inumaru, M. Misono, Microstructure of Cesium Hydrogen Salts of 12-Tungstophosphoric Acid Relevant to Novel Acid Catalysis, Chem. Mater., 12, 2230-2238.10.1021/cm9907561Search in Google Scholar
[27] T. Okuhara, N. Mizuno, M. Misono, Catalytic Chemistry of Heteropoly Compounds, Adv. Catalysis. 41 (1996) 103–252.10.1016/S0360-0564(08)60041-3Search in Google Scholar
[28] T. Okuhara. N. Mizuno. M. Misono, Catalysis by heteropoly compounds—recent developments, Appl. Catal. A Gen. 222 (2001) 63–77.10.1016/S0926-860X(01)00830-4Search in Google Scholar
[29] C. M. Patel, M. Chakraborty, Z.V.P. Murthy, Preparation of fenofibrate nanoparticles by combined stirred media milling and ultrasonication method, Ultrason. Sonochem. 21 (2014) 1100–1107.10.1016/j.ultsonch.2013.12.001Search in Google Scholar
[30] C. Perego. P. Ingallina, Recent advances in the industrial alkylation of aromatics: new catalysts and new processes, Catal. Today 73 (2002) 3–22.10.1016/S0920-5861(01)00511-9Search in Google Scholar
[31] D.V. Pinjari, K. Prasad, P.R. Gogate, S.T. Mhaske, A.B. Pandit, Intensification of synthesis of zirconium dioxide using ultrasound: Effect of amplitude variation, Chem. Eng. Process. 74 (2013) 178– 186.10.1016/j.cep.2013.09.010Search in Google Scholar
[32] V. Polshettiwar and R. S. Varma, Green chemistry by nano-catalysis, The Royal Society of Chemistry 12 (2010) 743–754.10.1039/b921171cSearch in Google Scholar
[33] M. Salavati-Niasari, L. Saleh, F. Mohandes, A. Ghaemi, Sonochemical preparation of pure t-LaVO4 nanoparticles with the aid of tris(acetylacetonato)lanthanum hydrate as a novel precursor, Ultrason. Sonochem. 21 (2014) 653–662.10.1016/j.ultsonch.2013.09.007Search in Google Scholar PubMed
[34] Z. Shobeiri, M. Pourayoubi, A. Heydari, T.M. Percino, A.L. Ramı´rez Marco, Ultrasound assisted synthesis of Cs2.5H0.5PW12O40: An efficient nano-catalyst for preparation of β-amino ketones via aza-Michael addition reactions, C. R. Chimie, 14 (2011) 597–603.10.1016/j.crci.2011.03.002Search in Google Scholar
[35] X. Wang, J.C. Yu, P. Liu, X. Wang, W. Sua, X. Fua, ’Probing of photocatalytic surface sites on SO42−/TiO2 solid acids by in situ FT-IR spectroscopy and pyridine adsorption, J. Photochem. Photobiol. A. 179 (2006) 339–347.10.1016/j.jphotochem.2005.09.007Search in Google Scholar
[36] L. Xuezheng, Novel magnetic carbon based solid acid for alkylation of benzene and dodecene, Chem. Eng. Journal 264 (2015) 251–257.10.1016/j.cej.2014.11.105Search in Google Scholar
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