Abstract
4-Chloro-2,6-pyridinedicarboxylic acid (CPDA) functionalized mesoporous silica SBA-15 nanocomposites (SBA/5CPDA) were synthesized and characterized for the Knoevenagel condensation of syringaldehyde and acetaldehyde to synthesize sinapaldehyde in the liquid phase. The physicochemical characterization of the SBA/CPDA nanocomposites showed the decrease in the surface properties (surface area, pore size, pore volume) compared to SBA-15 confirming the complete functionalization of CPDA inside the mesopores of SBA-15 materials. The catalytic activity results displayed high activity (~90%) and selectivity (90–95%) of the desired product (sinapaldehyde) under environmental friendly conditions. All the reaction parameters were optimized to accomplish the maximum conversion of the selective products. Finally, the mechanism of the formation of the products was proposed and discussed.
Similar content being viewed by others
REFERENCES
Margolese, D., Melero, J., Christiansen, S., Chmelka, B., and Stucky, G., Chem. Mater., 2000, vol. 12, p. 2448.
Wang, X., Lin, K.S., Chan, J.C., and Cheng, S., J. Phys. Chem. B, 2005, vol. 109, p. 1763.
Wu, S., Han, Y., Zou, Y.C., Song, J.W., Zhao, L., Di, Y., Liu, S.Z., and Xiao, F.S., Chem. Mater., 2004, vol. 16, p. 486.
Sharma, A., Wilson, G.R., and Dubey, A., New J. Chem., 2016, vol. 40, p. 764.
Rostamnia, S., Doustkhah, E., Estakhri, S., and Karimi, Z., Phys. E(Amsterdam,Neth.), 2016, vol. 76, p. 146.
Carraher, C.E., Slawek, P.P., Roner, M.R., Moric-Johnson, A., Miller, L.C., Einkauf, J.D., and Russell, F., J. Inorg. Organomet. Polym. Mater., 2016, vol. 26, p. 1338.
Yusof, N., Mehamod, F., Kadir, M., and Suah, F., IOP Conf. Ser.: Mater. Sci. Eng., 2018, vol. 440, p. 012 005.
Bhardwaj, S.K., Bhardwaj, N., Mohanta, G.C., Kumar, P., Sharma, A.L., Kim, K.-H., and Deep, A., ACS Appl. Mater. Interfaces, 2015, vol. 7, p. 26 124.
Batalha, I.L., Ke, P., Tejeda-Montes, E., Uddin, S., van der, Walle, C.F., and Christie, G., Int. J. Pharm., 201, vol. 7526, p. 332.
Lin, W. and Long, J.R., Inorg. Chem., 2016, vol. 55, p. 7189.
Ranjbar, M., Taher, M.A., and Sam, A., J. Mater. Sci. Mater. Electron., 2016, vol. 27, p. 1449.
Gu, X., Lv, W., Hui, Y., Liu, X., Wu, M., Yang, Y., and She, S., Zeitschrift für anorganischeund allgemeine Chemie, 2019, vol. 645, p. 663.
Macauley, E., and Hong, A., J. Hazard. Mater., 1995, vol. 40, p. 257.
Gang, D., Banerji, S.K., and Clevenger, T.E., Practice Periodical of Hazardous, Toxic, Radioactive Waste Management, 2000, vol. 4, p. 105.
Cha, D.K., Song, J.S., Sarr, D., and Kim, B., Water Environ. Res., 1996, vol. 68, p. 575.
Paulsson, M. and Parkås, J., BioResources, 2012, vol. 7, p. 5995.
Susanne, M.M.-J., Gaston, T.R.P.J., and Achille, P.G., Google Patents, 1960.
Schwab, W., Davidovich-Rikanati, R., and Lewinsohn, E., Plant J., 2008, vol. 54, p. 712.
Cheng, S.-S., Liu, J.-Y., Chang, E.-H., and Chang, S.-T., Bioresour. Technol., 2008, vol. 99, p. 5145.
Battistuzzi, G., Cacchi, S., and Fabrizi, G., Org. Lett., 2003, vol. 5, p. 777.
Kaleta, Z., Tárkányi, G., Gömöry, Á., Kálmán, F., Nagy, T., and Soós, T., Org. Lett., 2006, vol. 8, p. 1093.
Knoevenagel, E., Ber. Dtsch. Chem. Ges., 1898, vol. 31, p. 2596.
Hayashi, Y., Toyoshima, M., Gotoh, H., and Ishikawa, H., Org. Lett., 2008, vol. 11, p. 45.
Maga, J.A., Food Rev. Int., 1987, vol. 3, p. 139.
Brill, E.M., Abrahams, S., Hayes, C.M., Jenkins, C.L., and Watson, J.M., Plant. Mol. Biol., 1999, vol. 41, p. 279.
Pan, H., Zhou, R., Louie, G.V., Mühlemann, J.K., Bomati, E.K., Bowman, M.E., Dudareva, N., Dixon, R.A., Noel, J.P., and Wang, X., Plant. Cell, 2014, vol. 26, p. 3709.
Dubey, A., Sachdev, D., and Srivasatava, N.M., Adv. Mater. Lett., 2013, vol. 4, p. 39.
Galarneau, A., Cambon, H.L.N., Renzo, F.D., and Ryoo, R.N., J. Chem., 2000, vol. 27, p. 73.
Kruk, M., Jaroniec, M., Ko, C.H., and Ryoo, R., Chem. Mater., 2000, vol. 12, p. 1961.
Sachdev, D., Wilson, G.R., Srivastava, N.M., and Dubey, A., Catal. Commun., 2014, vol. 51, p. 90.
Yang, C.M., Liu, P.H., Ho, Y.F., Chiu, C.Y., and Chao, K.J., Chem. Mater., 2003, vol. 15, p. 275.
Katiyar, A., Yadav, S., Smirniotis, P.G., and Pinto, N.G., J. Chromatogr. A, 2006, vol. 1122, p. 13.
Konradova, D., Kozubikova, H., Doležal, K., and Pospíšil J., Eur. J. Org. Chem., 2017, p. 5204.
Nakamura, Y., Nakatsubo, F., and Higuchi, T., Wood Res., 1974, vol. 56, p. 1.
Verma, S., and Dubey, A., J. Nanopart. Res., 2017, vol. 19, p. 407.
Tichit, D., Lutic, D., Coq, B., Durand, R., and Teissier, R., J. Catal., 2003, vol. 219, p. 167.
Tichit, D., Bennani, M.N., Figueras, F., Tessier, R., and Kervennal, J., Appl. Clay Sci., 1998, vol. 13, p. 401.
ACKNOWLEDGMENTS
Authors thank the institute for necessary help and support.
Author information
Authors and Affiliations
Corresponding author
Additional information
Abbreviations: PDA, pyridine-2,6-dicarboxylic acid; CPDA, 4‑chloro-2,6-pyridinedicarboxylic acid; SBA/CPDA, CPDA functionalized mesoprous silica SBA-15 nanocomposites; PXRD, powder X-ray diffraction; SEM, scanning electron microscopy.
Rights and permissions
About this article
Cite this article
Verma, S., Dubey, A. 4-Chloro-2,6-Pyridinedicarboxylic Acid Functionalized Mesoporous Silica Nanocomposites for the Synthesis of Sinapaldehyde. Kinet Catal 61, 112–118 (2020). https://doi.org/10.1134/S0023158420010103
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0023158420010103