Abstract
In this study, the magnetic nanoparticles have been loaded on the halloysite nanotubes (HNTs) as an aluminosilicate clay mineral. Fe3O4/HNTs nanocomposite was fully characterized by Fourier transform infrared (FT-IR) spectroscopy, energy dispersive X-ray (EDX) analysis, thermogravimetric analysis (TGA), field-emission scanning electron microscopy (FE-SEM) image, transmission electron microscope (TEM) image, inductively coupled plasma (ICP) analysis, X-ray diffraction (XRD) pattern and vibrating sample magnetometer (VSM) curve. The performance of the Fe3O4/HNTs as a heterogeneous catalyst was investigated in the synthesis of 4H-pyran derivatives. The high efficiently, mild reaction condition, green solvents and using the eco-friendly and recoverable catalyst are the most advantages of the present work. Moreover, the simple separation and reuse of the Fe3O4/HNTs nanocatalyst were confirmed stability and efficiency of the catalyst after 7 runs.
Similar content being viewed by others
References
Bergaya F, Lagaly G (2013) Developments in. Clay Sci 5:1–7
Lvov Y, Aerov A, Fakhrullin R (2014) Clay nanotube encapsulation for functional biocomposites. Adv Colloid Interf Sci 207:189–198
Lvov Y, Wang W, Zhang L, Fakhrullin R (2016) Halloysite Clay Nanotubes for Loading and Sustained Release of Functional Compounds. Adv Mater 28:1227–1250
Liu M, Jia Z, Jia D, Zhou C (2014) Recent advance in research on halloysite nanotubes-polymer nanocomposite. Prog Polym Sci 39:1498–1525
Hajizadeh Z, Maleki A (2018) Poly(ethylene imine)-modified magnetic halloysite nanotubes: A novel, efficient and recyclable catalyst for the synthesis of dihydropyrano[2,3-c]pyrazole derivatives. Mole Catal 460:87–93
Suresh G, Vasu V, Rao MV (2018) A Composite (Taguchi-Utility-RSM) Approach for Optimizing the Tribological Responses of Polytetrafluoroethylene (PTFE) Nanocomposites for Self-lubrication Applications. Silicon 10:2043–2053
Riahi-Madvaar R, Taher MA, Fazelirad H (2017) Synthesis and characterization of magnetic halloysite-iron oxide nanocomposite and its application for naphthol green B removal. Appl Clay Sci 137:101–106
Chen L, Zhou CH, Fiore S, Tong DS, Zhang H, Li CS, Ji SF, Yu WH (2016). Appl Clay Sci 127:143–163
Fattahi N, Ramazani A, Kinzhybalo V (2018). Silicon. https://doi.org/10.1007/s12633-017-9757-0
Fattahi N, Ramazani A, Ahankar H, Azimzadeh Asiabi P, Kinzhybalo V (2018) Tetramethylguanidine-Functionalized Fe3O4/ Chloro-Silane Core-Shell Nanoparticles: an Efficient Heterogeneous and Reusable Organocatalyst for Aldol Reaction. Silicon. https://doi.org/10.1007/s12633-018-9954-5
Maleki A, Aghaei M (2017) Ultrasonic assisted synergetic green synthesis of polycyclic imidazo(thiazolo)pyrimidines by using Fe3O4 @clay core-shell. Ultrason Sonochem 38:585–589
Maleki A, Firozi-Haji R, Hajizadeh Z (2018) Magnetic guanidinylated chitosan nanobiocomposite: A green catalyst for the synthesis of 1,4-dihydropyridines. Int J Biol Macromol 116:320–326
Tian X, Wang W, Tian N, Zhou C, Yang C, Komarneni S (2016) Cr(VI) reduction and immobilization by novel carbonaceous modified magnetic Fe3O4 /halloysite nanohybrid. J Hazard Mater 309:151–156
Tsoufis T, Katsaros F, Kooi BJ, Bletsa E, Papageorgiou S, Deligiannakis Y, Panagiotopoulos I (2017) Halloysite nanotube-magnetic iron oxide nanoparticle hybrids for the rapid catalytic decomposition of pentachlorophenol. Chem Eng J 313:466–474
Mu B, Wang W, Zhang J, Wang A (2014) Superparamagnetic sandwich structured silver/halloysite nanotube/Fe3O4 nanocomposites for 4-nitrophenol reduction. RSC Adv 4:39439–39445
Xie Y, Qian D, Wu D, Ma X (2011) Magnetic halloysite nanotubes/iron oxide composites for the adsorption of dyes. Chem Eng J 168:959–963
Rostamnia S, Alamgholiloo H, Jafari M (2018) Appl Organomet Chem 32:e4370–e4379
Maleki A, Hajizadeh Z, Abbasi H (2018) Carbon Lett 27:42–49
Azzam RA, Mohareb RM (2015) Multicomponent Reactions of Acetoacetanilide Derivatives with Aromatic Aldehydes and Cyanomethylene Reagents to Produce 4<i>H</i>-Pyran and 1,4-Dihydropyridine Derivatives with Antitumor Activities. Chem Pharm Bull 63:1055–1064
Maleki A, Ghassemi M, Firouzi-Haji R (2018) Green multicomponent synthesis of four different classes of six-membered N-containing and O-containing heterocycles catalyzed by an efficient chitosan-based magnetic bionanocomposite. Pure Appl Chem 90:387–394
Hekmatshoar R, Majedi S, Bakhtiari K (2008) Sodium selenate catalyzed simple and efficient synthesis of tetrahydro benzo[b]pyran derivatives. Catal Commun 9:307–310
Niknam K, Borazjani N, Rashidian R, Jamali A (2013) Silica-bonded N-propylpiperazine sodium n-propionate as recyclable catalyst for synthesis of 4H-pyran derivatives. Chin J Catal 34:2245–2254
Maleki B, Sheikh S (2015) One-pot Synthesis of 2-Amino-2-chromene and 2-Amino-3-cyano-4H-pyran Derivatives Promoted by Potassium Fluoride. Org Prep Proced Int 47:368–378
Maleki A (2013) Tetrahedron Lett 54:2055–2059
Maleki A (2018) Ultrason Sonochem 40:460–464
Maleki A (2018) Polycycl Aromat Compd 38:402–409
Maleki A, Rahimi J, Hajizadeh Z, Niksefat M (2019) J Organomet Chem 881:58-65
Maleki A (2014) Helv Chim Acta 97:587–593
Li C, Li X, Duan X, Li G, Wang J (2014) Halloysite nanotube supported Ag nanoparticles heteroarchitectures as catalysts for polymerization of alkylsilanes to superhydrophobic silanol/siloxane composite microspheres. J Colloid Interface Sci 436:70–76
Maleki A, Hajizadeh Z, Firouzi-Haji R (2018) Eco-friendly functionalization of magnetic halloysite nanotube with SO3H for synthesis of dihydropyrimidinones. Microporous Mesoporous Mater 259:46–53
Maleki A, Akhlaghi E, Paydar R (2016) Design, synthesis, characterization and catalytic performance of a new cellulose-based magnetic nanocomposite in the one-pot three-component synthesis of α-aminonitriles. Appl Organometal Chem 30:382–386
Johnson SL, Guggenheim S, van Groos AF (1990) Thermal Stability of Halloysite by High-Pressure Differential Thermal Analysis. Clay Clay Miner 38:477–484
Wang XS, Shi DQ, Tu ST, Yao CS (2003) A Convenient Synthesis of 5-Oxo-5,6,7,8-tetrahydro-4H-benzo-[b]-pyran Derivatives Catalyzed by KF-Alumina. Synth Commun 33:119–126
Wang LM, Shao JH, Tian H, Wang YH, Liu B (2006) Rare earth perfluorooctanoate [RE(PFO)3] catalyzed one-pot synthesis of benzopyran derivatives. J Fluor Chem 127:97–100
Jin TS, Wang AQ, Wang X, Zhang JS, Li TS (2004). Synlett 5:871–873
Pourian E, Javanshir S, Dolatkhah Z, Molaei S, Maleki A (2018) Ultrasonic-Assisted Preparation, Characterization, and Use of Novel Biocompatible Core/Shell Fe3O4@GA@Isinglass in the Synthesis of 1,4-Dihydropyridine and 4H-Pyran Derivatives. ACS Omega 3:5012–5020
Moshtaghi Zonouz AA, Moghani D, Okhravi S (2014) A facile and efficient protocol for the synthesis of 2-amino-3-cyano-4H-pyran derivatives at ambient temperature. Curr Chem Lett 3:71–74
Acknowledgements
The authors gratefully acknowledge the partial support from the Research Council of the Iran University of Science and Technology.
Author information
Authors and Affiliations
Electronic supplementary material
ESM 1
(DOC 242 kb)
Rights and permissions
About this article
Cite this article
Maleki, A., Hajizadeh, Z. Magnetic Aluminosilicate Nanoclay: a Natural and Efficient Nanocatalyst for the Green Synthesis of 4H-Pyran Derivatives. Silicon 11, 2789–2798 (2019). https://doi.org/10.1007/s12633-019-0069-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12633-019-0069-4