Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Synthesis of SrCO3 Nanoparticles Supported on Montmorillonite as Efficient Catalyst in the Preparation of α, ά-bis(substituted benzylidene) cycloalkanones

Author(s): Azim Mohammadpour and Enayatollah Sheikhhosseini*

Volume 19, Issue 11, 2022

Published on: 27 April, 2022

Page: [983 - 992] Pages: 10

DOI: 10.2174/1570178619666220314145346

Price: $65

Abstract

In the present study, the SrCO3@montmorillonite nanocomposite was synthesized by loading Sr(NO3)2 on natural bentonite using a controlled and facile microwave method. The SrCO3@montmorillonite nanoparticles’ characteristics are identified using advanced techniques, such as infrared spectroscopy (IR), energy‐dispersive X‐ray analysis (EDX), X-ray diffraction analysis (XRD), scanning electron microscopy (SEM), and pore size distribution analysis. Crossed-aldol condensation of an aromatic aldehyde with cycloalkanone in the presence of these nanoparticles produced α, ά-bis(substituted-benzylidene) cycloalkanones in good yields without using any solvent. The present method is operationally simple and dose not use organic solvent, which makes the process environmentally benign.

Keywords: SrCO3 nanoparticles, solvent free, microwave method, α, α-bis(substituted-benzylidene) cycloalkanone, bentonite, cross-aldol condensation.

« Previous Next »
Graphical Abstract

[1]
Jacob, D.S.; Joseph, A.; Mallenahalli, S.P.; Shanmugam, S.; Makhluf, S.; Calderon-Moreno, J.; Koltypin, Y.; Gedanken, A. Angew. Chem. Int. Ed., 2005, 44(40), 6560-6563.
[http://dx.doi.org/10.1002/anie.200501446] [PMID: 16158455]
[2]
Ma, H.; Bai, X.; Zheng, L. CrystEngComm, 2011, 13, 3788-3793.
[http://dx.doi.org/10.1039/c1ce05086a]
[3]
Wei, W.; Ma, G.H.; Hu, G.; Yu, D.; McLeish, T.; Su, Z.G.; Shen, Z.Y. J. Am. Chem. Soc., 2008, 130(47), 15808-15810.
[http://dx.doi.org/10.1021/ja8039585] [PMID: 18980322]
[4]
Du, J.; Liu, Z.; Li, Z.; Han, B.; Huang, Y.; Zhang, J. Microporous Mesoporous Mater., 2005, 83, 145-149.
[http://dx.doi.org/10.1016/j.micromeso.2005.04.005]
[5]
Akiyama, M.; Xu, C.N.; Liu, Y.; Nonaka, K.; Watnabe, T. J. Lumin., 2002, 97, 13-18.
[http://dx.doi.org/10.1016/S0022-2313(01)00419-7]
[6]
Tang, Z.L.; Zhang, F.; Zhang, Z.T.; Huang, C.Y.; Lin, Y.H. J. Eur. Ceram. Soc., 2000, 20, 2129-2132.
[http://dx.doi.org/10.1016/S0955-2219(00)00092-3]
[7]
Bingol, D.; Aydogan, S.; Bozbas, S.K. J. Ind. Eng. Chem., 2012, 18, 834-838.
[http://dx.doi.org/10.1016/j.jiec.2011.11.145]
[8]
Martinez-Luevanos, A.; Uribe-Salas, A.; Lopez-Valdivieso, A. Miner. Eng., 1999, 12, 919-936.
[http://dx.doi.org/10.1016/S0892-6875(99)00078-3]
[9]
Griffiths, J. Ind Miner, 1985, 218, 21.
[10]
Massone, J.; Coope, M.B.; Clarke, G.M. Industrial Minerals; Metal Bullentin: London, 1982.
[11]
Roskill The Economics of Strontium, 5th ed; Roskill Information Services: London, 1989.
[12]
Li, S.; Zhang, H.; Xu, J.; Yang, D. Mater. Lett., 2005, 59, 420-422.
[http://dx.doi.org/10.1016/j.matlet.2004.09.037]
[13]
Huang, Q.; Gao, L.; Cai, Y.; Aldinger, F. Chem. Lett., 2004, 33, 290-291.
[http://dx.doi.org/10.1246/cl.2004.290]
[14]
Shi, L.; Du, F. Mater. Lett., 2007, 61, 3262-3264.
[http://dx.doi.org/10.1016/j.matlet.2006.11.050]
[15]
Yang, J.; Liu, X.M.; Li, C.X.; Quan, Z.W.; Kong, D.Y.; Lin, J. J. Cryst. Growth, 2007, 303, 480-486.
[http://dx.doi.org/10.1016/j.jcrysgro.2006.12.069]
[16]
Cao, M.; Wu, X.; He, X.; Hu, C. Langmuir, 2005, 21(13), 6093-6096.
[http://dx.doi.org/10.1021/la050736f] [PMID: 15952865]
[17]
Ma, M.G.; Zhu, Y. J. Mater. Lett., 2008, 62, 2512-2515.
[http://dx.doi.org/10.1016/j.matlet.2007.12.034]
[18]
Bilecka, I.; Niederberger, M. Nanoscale, 2010, 2(8), 1358-1374.
[http://dx.doi.org/10.1039/b9nr00377k] [PMID: 20845524]
[19]
Jin, S.; Dong, G.; Luo, J.; Ma, F.; Wang, C. Appl. Catal. B, 2018, 227, 24-34.
[http://dx.doi.org/10.1016/j.apcatb.2018.01.020]
[20]
Omata, K.; Kobayashi, Y.; Yamada, M. Catal. Commun., 2007, 8, 1-5.
[http://dx.doi.org/10.1016/j.catcom.2006.04.018]
[21]
Wang, K.; Ji, S.; Shi, X. Tang. J. Catal. Commun., 2009, 10, 807-810.
[http://dx.doi.org/10.1016/j.catcom.2008.12.001]
[22]
Iida, H.; Fujiyama, A.; Igarashi, A.; Okumura, K. Fuel, 2020, 272, 117703.
[http://dx.doi.org/10.1016/j.fuel.2020.117703]
[23]
Fu, J.; Kyzas, G.Z.; Cai, Z.; Deliyanni, E.A.; Liu, W.; Zhao, D. Chem. Eng. J., 2018, 335, 290-300.
[http://dx.doi.org/10.1016/j.cej.2017.10.163]
[24]
Lu, P.; Hu, X.; Li, Y.; Zhang, M.; Liu, X.; He, Y.; Dong, F.; Fu, M.; Zhang, Z. RSC Advances, 2018, 8, 6315-6325.
[http://dx.doi.org/10.1039/C7RA11565B]
[25]
Deli, J.; Lóránd, T.; Szabó, D.; Földesi, A. Pharmazie, 1984, 39(8), 539-540.
[PMID: 6504976]
[26]
Xiaofang, L.; Xianyong, Y.; Yaqing, F. Chin. J. Chem., 2009, 27, 1531-1536.
[http://dx.doi.org/10.1002/cjoc.200990258]
[27]
Leonard, N.J.; Miller, L.A.; Berry, J.W. J. Am. Chem. Soc., 1957, 79, 1482-1485.
[http://dx.doi.org/10.1021/ja01563a056]
[28]
Ciufolini, M.A.; Byrne, N.E. J. Am. Chem. Soc., 1991, 113, 8016-8024.
[http://dx.doi.org/10.1021/ja00021a031]
[29]
Modzelewska, A.; Pettit, C.; Achanta, G.; Davidson, N.E.; Huang, P.; Khan, S.R. Bioorg. Med. Chem., 2006, 14(10), 3491-3495.
[http://dx.doi.org/10.1016/j.bmc.2006.01.003] [PMID: 16434201]
[30]
Robinson, T.P.; Hubbard, R.B., IV; Ehlers, T.J.; Arbiser, J.L.; Goldsmith, D.J.; Bowen, J.P. Bioorg. Med. Chem., 2005, 13(12), 4007-4013.
[http://dx.doi.org/10.1016/j.bmc.2005.03.054] [PMID: 15911313]
[31]
Lee, K.H.; Ab Aziz, F.H.; Syahida, A.; Abas, F.; Shaari, K.; Israf, D.A.; Lajis, N.H. Eur. J. Med. Chem., 2009, 44(8), 3195-3200.
[http://dx.doi.org/10.1016/j.ejmech.2009.03.020] [PMID: 19359068]
[32]
Inayama, S.; Mamoto, K.; Shibata, T.; Hirose, T. J. Med. Chem., 1976, 19(3), 433-436.
[http://dx.doi.org/10.1021/jm00225a022] [PMID: 1255669]
[33]
Hall, I.H.; Carlson, G.L.; Abernethy, G.S.; Piantadosi, C. J. Med. Chem., 1974, 17(12), 1253-1257.
[http://dx.doi.org/10.1021/jm00258a004] [PMID: 4372350]
[34]
Kawamata, J.; Inoue, K.; Inabe, T.; Kiguchi, M.; Kato, M.; Taniguchi, Y. Chem. Phys. Lett., 1996, 249, 29-34.
[http://dx.doi.org/10.1016/0009-2614(95)01373-3]
[35]
Dinkova-Kostova, A.T.; Abeygunawardana, C.; Talalay, P. J. Med. Chem., 1998, 41(26), 5287-5296.
[http://dx.doi.org/10.1021/jm980424s] [PMID: 9857096]
[36]
Gall, E.L.; Texier-Boullet, F. Hamelin. J. Synth. Commun., 1999, 29, 3651-3657.
[http://dx.doi.org/10.1080/00397919908086000]
[37]
Reddick, J.J.; Cheng, J.; Roush, W.R. Org. Lett., 2003, 5(11), 1967-1970.
[http://dx.doi.org/10.1021/ol034555l] [PMID: 12762698]
[38]
Chandru, H.; Sharada, A.C.; Bettadaiah, B.K.; Kumar, C.S.A.; Rangappa, K.S.; Sunila, J.K.; Jayashree, K. Bioorg. Med. Chem., 2007, 15(24), 7696-7703.
[http://dx.doi.org/10.1016/j.bmc.2007.08.051] [PMID: 17869527]
[39]
Hathaway, B.A. J. Chem. Educ., 1987, 64, 367.
[http://dx.doi.org/10.1021/ed064p367]
[40]
Singh, N.; Pandey, J.; Yadav, A.; Chaturvedi, V.; Bhatnagar, S.; Gaikwad, A.N.; Sinha, S.K.; Kumar, A.; Shukla, P.K.; Tripathi, R.P. Eur. J. Med. Chem., 2009, 44(4), 1705-1709.
[http://dx.doi.org/10.1016/j.ejmech.2008.09.026] [PMID: 18952325]
[41]
Nakano, T.; Migita, T. Chem. Lett., 1993, 22, 2175-21588.
[http://dx.doi.org/10.1246/cl.1993.2157]
[42]
Wang, L.; Sheng, J.; Tian, H.; Han, J.; Fan, Z.; Qian, C. Synthesis, 2004, 18, 3060-3064.
[http://dx.doi.org/10.1055/s-2004-834900]
[43]
Deng, G.; Ren, T. Synth. Commun., 2003, 33, 2995-3001.
[http://dx.doi.org/10.1081/SCC-120022473]
[44]
Li, J.; Su, W.; Li, N. Synth. Commun., 2005, 35, 3037-3043.
[http://dx.doi.org/10.1080/00397910500278735]
[45]
Wang, J.X.; Kang, L.; Hu, Y.; Wei, B.G. Synth. Commun., 2002, 32, 1691-1696.
[http://dx.doi.org/10.1081/SCC-120004261]
[46]
Solhy, A.; Amer, W.; Karkouri, M.; Tahir, R.; Bouari, A.E.; Fihri, A.; Bousmina, M.; Zahouily, M. J. Mol. Catal. Chem., 2011, 336, 8-15.
[http://dx.doi.org/10.1016/j.molcata.2010.11.032]
[47]
Ziarani, G.M.; Badiei, A.; Abbasi, A.; Farahani, Z. Chin. J. Chem., 2009, 27, 1537-1542.
[http://dx.doi.org/10.1002/cjoc.200990259]
[48]
An, L.T.; Zou, J.P.; Zang, L.L. Catal. Commun., 2008, 9, 349-354.
[http://dx.doi.org/10.1016/j.catcom.2007.06.004]
[49]
Iranpoor, N.; Zeynizadeh, B.; Aghapour, A. J. Chem. Res., 1999, 9, 554-555.
[50]
Das, B.; Thirupathi, P.; Mahender, I.; Reddy, K.R. J. Mol. Catal. Chem., 2006, 247, 182-185.
[http://dx.doi.org/10.1016/j.molcata.2005.11.044]
[51]
Yadav, J.S.; Reddy, B.S.; Nagaraju, A.; Sarma, J.A.R.P. Synth. Commun., 2002, 32, 893-896.
[http://dx.doi.org/10.1081/SCC-120002700]
[52]
Sheikhhosseini, E.; Ahmadi, S.A.; Sadeghi, S. J. Appl. Commun. Res., 2014, 8, 25-30.
[53]
Patil, R.C.; Patil, U.P.; Jagdale, A.A.; Shinde, S.K.; Patil, S.S. Res. Chem. Intermed., 2020, 46, 3527-3543.
[http://dx.doi.org/10.1007/s11164-020-04160-5]
[54]
Ardanaz, S.M.; Borucki, E.L.; Rueda, A.J.V.; Parisi, G.; Iribarren, A.M.; Iglesias, L.E. Process Biochem., 2019, 86, 50-57.
[http://dx.doi.org/10.1016/j.procbio.2019.08.003]
[55]
Sluban, M.; Cojocaru, B.; Parvulescu, V.I.; Iskra, J.; Korosec, R.C.; Umek, P. J. Catal., 2017, 346, 161-169.
[http://dx.doi.org/10.1016/j.jcat.2016.12.015]
[56]
Amoozadeh, A.; Tabrizian, E.; Rahmani, S. C. R. Chim., 2015, 18, 848-857.
[http://dx.doi.org/10.1016/j.crci.2014.11.003]
[57]
Karimzadegan, H.; Akhlaghinia, B.; Ghasemzadeh, M.S. Iran. J. Catal, 2019, 9, 109-120.
[58]
Yahyazadehfar, M.; Sheikhhosseini, E.; Ahmadi, S.A.; Ghazanfari, D. Appl. Organomet. Chem., 2019, 33, e5100.
[59]
Maaref, H.; Sheikhhosseini, E.; Foroughi, M.M.; Akhgar, M.R.; Jahani, S. Appl. Organomet. Chem., 2020, 34, e5557.
[http://dx.doi.org/10.1002/aoc.5557]
[60]
Yahyazadehfar, M.; Ahmadi, S.A.; Sheikhhosseini, E.; Ghazanfari, D. J. Mater. Sci. Mater. Electron., 2020, 31, 11618-11623.
[http://dx.doi.org/10.1007/s10854-020-03710-2]
[61]
Xia, P.; Zhu, B.; Cheng, B.; Yu, J.; Xu, J. ACS Sustain. Chem.& Eng., 2018, 6, 965-973.
[http://dx.doi.org/10.1021/acssuschemeng.7b03289]

Rights & Permissions Print Cite
Article Metrics
19
1
© 2024 Bentham Science Publishers | Privacy Policy