Abstract
This paper presents a feasible protocol for the preparation of β-cyclodextrin conjugated Fe3O4 magnetic nanoparticles as an efficient microvessel and host system for nucleophilic substitution reaction of benzyl halides in water. No evidence for the formation of by-product for example isothiocyanate or benzyl alcohol was observed and the products were obtained in pure form without further purification. The characteristics results of FT-IR, XRD, TGA and SEM shows that β-CD is grafted onto Fe3O4 nanoparticles. The nanomagnetic catalyst could be readily separated from solution via application of an external magnet, allowing straightforward recovery and reuse.
This is a preview of subscription content, access via your institution.





References
Szejtli, J.: Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98, 1743–1753 (1998)
Calsavara, L., Zanin, G., Moraes, F.D.: Enrofloxacin inclusion complexes with cyclodextrins. J. Inclusion Phenom. Macrocyclic Chem. (2011). doi:10.1007/s10847-011-0045-0
Kiasat, A.R., Sayyahi, S.: Immobilization of β-cyclodextrin onto Dowex resin as a stationary microvessel and phase transfer catalyst. Catal. Commun. 11, 484–486 (2010)
Youming, Z., Xinrong, D., Liangcheng, W., Taibao, W.: Synthesis and characterization of inclusion complexes of aliphatic-aromatic poly(Schiff base)s with β-cyclodextrin. J. Inclusion Phenom. Macrocyclic Chem. 60, 313–319 (2008)
Chen, H., Ji, H., Zhou, X., Wang, L.: Green synthesis of natural benzaldehyde from cinnamon oil catalyzed by hydroxypropyl-β-cyclodextrin. Tetrahedron 66, 9888–9893 (2010)
Carvalho, L.B., Pinto, L.: Formation of inclusion complexes and controlled release of atrazine using free or silica-anchored β-cyclodextrin. J. Inclusion Phenom. Macrocyclic Chem. (2012). doi:10.1007/s10847-012-0125-9
Mohamed, M.H., Wilson, L.D., Headley, J.V., Peru, K.M.: A spectral displacement study of cyclodextrin/naphthenic acids inclusion complexes. Can. J. Chem. 87, 1747–1756 (2009)
Poon, K.H.N., Cheng, Y.L.: A quartz crystal microbalance study of β-cyclodextrin self assembly on gold and complexation of immobilized β-cyclodextrin with adamantane derivatives. J. Inclusion Phenom. Macrocyclic Chem. 60, 211–222 (2008)
Cole-Hamilton, D.J.: Homogeneous catalysis—new approaches to catalyst separation, recovery and recycling. Science 299, 1702–1706 (2003)
Du, X., He, J., Zhu, J., Sun, L., An, S.: Ag-deposited silica-coated Fe3O4 magnetic nanoparticles catalyzed reduction of p-nitrophenol. Appl. Surf. Sci. 258, 2717–2723 (2012)
Gill, C.S., Price, B.A., Jones, C.W.: Sulfonic acid-functionalized silica-coated magnetic nanoparticle catalysts. J. Catal. 251, 145–152 (2007)
Fana, L., Li, M., Lva, Z., Suna, M., Luoa, C., Lua, F., Qiua, H.: Fabrication of magnetic chitosan nanoparticles grafted with β-cyclodextrin as effective adsorbents toward hydroquinol. Colloids Surf. B 95, 42–49 (2012)
Pyun, J.: Nanocomposite materials from functional polymers and magnetic colloids. Polym. Rev. 47, 231–263 (2007)
Kassaee, M.Z., Masrouri, H., Movahedi, F.: Sulfamic acid-functionalized magnetic Fe3O4 nanoparticles as an efficient and reusable catalyst for one-pot synthesis of α-amino nitriles in water. Appl. Catal. A 395, 28–33 (2011)
Badruddoza, A.Z.M., Hidajat, K., Uddin, M.S.: Synthesis and characterization of b-cyclodextrin-conjugated magnetic nanoparticles and their uses as solid-phase artificial chaperones in refolding of carbonic anhydrase bovine. J. Colloid Interface Sci. 346, 337–346 (2010)
Badruddoza, A.Z.M., Tay, A.S.H., Tan, P.Y., Hidajat, K., Uddin, M.S.: Carboxymethyl-β-cyclodextrin conjugated magnetic nanoparticles as nanoadsorbents for removal of copper ions: synthesis and adsorption studies. J. Hazard. Mater. 185, 1177–1186 (2011)
Cao, H., He, J., Deng, L., Gao, X.: Fabrication of cyclodextrin-functionalized superparamagnetic Fe3O4/amino-silane core–shell nanoparticles via layer-by-layer method. Appl. Surf. Sci. 255, 7974–7980 (2009)
Akoz, E., Erdemir, S., Yilmaz, M.: Immobilization of novel the semicarbazone derivatives of calix[4]arene onto magnetite nanoparticles for removal of Cr(VI) ion. J. Inclusion Phenom. Macrocyclic Chem. (2011). doi:10.1007/s10847-011-0083-7
Wang, H., Zhou, Y., Guo, Y., Liu, W., Dong, C., Wu, Y., Li, S., Shuang, S.: β-Cyclodextrin/Fe3O4 hybrid magnetic nano-composite modified glassy carbon electrode for tryptophan sensing. Sens. ActuatorsB 163, 171–178 (2012)
Kiasat, A.R., Nazari, S.: Application of β-cyclodextrin-polyurethane as a stationary microvessel and solid–liquid phase-transfer catalyst: preparation of benzyl cyanides and azides in water. Catal. Commun. 18, 102–105 (2012)
Kiasat, A.R., Fallah Mehrjardi, M.: PEG-SO3H as eco-friendly polymeric catalyst for regioselective ring opening of epoxides using thiocyanate anion in water: an efficient route to synthesis of β-hydroxy thiocyanate. Catal. Commun. 9, 1497–1500 (2008)
Kiasat, A.R., Badri, R., Zargar, B., Sayyahi, S.: Poly(ethylene glycol) grafted onto Dowex resin: an efficient, recyclable, and mild polymer-supported phase transfer catalyst for the regioselective azidolysis of epoxides in water. J. Org. Chem. 73, 8382–8385 (2008)
Kiasat, A.R., Zayadi, M.: Polyethylene glycol immobilized on silica gel as a new solid–liquid phase-transfer catalyst for regioselective azidolysis of epoxides in water: an efficient route to 1,2-azido alcohols. Catal. Commun. 9, 2063–2067 (2008)
Can, K., Ozmen, M., Ersoz, M.: Immobilization of albumin on aminosilane modified superparamagnetic magnetite nanoparticles and its characterization. Colloids Surf. B 71, 154–159 (2009)
Donia, A.M., Atia, A.A., Abouzayed, F.I.: Preparation and characterization of nano-magnetic cellulose with fast kinetic properties towards the adsorption of some metal ions. Chem. Eng. J. (2011). doi:10.1016/j.cej.2011.08.034
Kiasat, A.R., Badri, R., Sayyahi, S.: A facile and convenient method for synthesis of alkyl thiocyanates under homogeneous phase transfer catalyst conditions. Chin. Chem. Lett. 19, 1301–1304 (2008)
Acknowledgments
We are grateful to the Research Council of Shahid Chamran University for financial support.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kiasat, A.R., Nazari, S. β-Cyclodextrin conjugated magnetic nanoparticles as a novel magnetic microvessel and phase transfer catalyst: synthesis and applications in nucleophilic substitution reaction of benzyl halides. J Incl Phenom Macrocycl Chem 76, 363–368 (2013). https://doi.org/10.1007/s10847-012-0207-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10847-012-0207-8
Keywords
- Magnetic nanoparticles
- β-Cyclodextrin
- Nucleophilic substitution
- Benzyl thiocyanate
- Benzyl azide