Synthesis of Fe3O4/Eggshell Nanocomposite and Application for Preparation of Tetrahydrobenzo[b]Pyran Derivatives

Authors

Department of Chemistry, Shahid Bahonar University of Kerman, Kerman, 76169, Iran

Abstract

This work is reported on the synthesis of Fe3O4/eggshell nanocomposites in the absence of any stabilizer or surfactant. Fe3Omagnetic nanoparticles were established on the egg shell nano-composite. The nanocompositeshave shown high catalytic activities in the synthesis of Tetrahydrobenzo[b]pyran. These derivatives were synthesized via an one‐pot three‐component condensation of aromatic aldehydes with malononitrile and dimedonewith excellent yields in the presence of Fe3O4/eggshell nanocomposites as a highly efficient heterogeneous catalyst. The obtained catalyst was characterized by Fourier transform infrared spectroscopy (FT-IR), Field emission scanning electron microscopy (FE-SEM), X-ray diffraction analysis (XRD) and Vibrating sample magnetometer (VSM). The developed technique of nano-composite synthesis is energy efficient since the reactions carried out in single step. The present catalyst is possible to be used for the production of biodiesel.

Keywords


[1]   Fang D, Zhang H, Liu Z. 2010,Synthesis of 4H‐benzopyrans catalyzed by acyclic acidic ionic liquids in aqueous media. J Heterocycl Chem;47:63–7.

[2]   Mohamadpour F, Maghsoodlou MT, Heydari R, Lashkari M. A 2015, highly efficient synthesis of biologically active spiro [4H-pyran] derivatives with nano SiO2 as a mild catalyst under solvent-free conditions. J Chem Pharm Res;7:934–40.

[3]   Shestopalov AM, Emeliyanova YM, Shestopalov AA, Rodinovskaya LA, Niazimbetova ZI, Evans DH, 2002. One-Step Synthesis of Substituted 6-Amino-5-cyanospiro-4-(piperidine-4 ‘)-2 H, 4 H-dihydropyrazolo [3, 4-b] pyrans. Org Lett;4:423–5.

[4]   Chen L, Li Y, Huang X, Zheng W. N, 2009, N‐Dimethylamino‐functionalized basic ionic liquid catalyzed one‐pot multicomponent reaction for the synthesis of 4H‐benzo [b] pyran derivatives under solvent‐free condition. Heteroat Chem;20:91–4.

[5]   Hazeri N, Maghsoodlou MT, Mir F, Kangani M, Saravani H, Molashahi E. 2014, An efficient one-pot three-component synthesis of tetrahydrobenzo [b] pyran and 3, 4-dihydropyrano [c] chromene derivatives using starch solution as catalyst. Chinese J Catal;35:391–5.

[6]   Saini A, Kumar S, Sandhu JS., 2006. A new LiBr-catalyzed, facile and efficient method for the synthesis of 14-alkyl or aryl-14H-dibenzo [a, j] xanthenes and tetrahydrobenzo [b] pyrans under solvent-free conventional and microwave heating. Synlett;2006:1928–32.

[7]   Pandey G, Singh RP, Garg A, Singh VK. 2005, Synthesis of Mannich type products via a three-component coupling reaction. Tetrahedron Lett;46:2137–40.

[8]   Thompson R, Doggrell S, Hoberg JO. 2003, Potassium channel activators based on the benzopyran substructure: Synthesis and activity of the C-8 substituent. Bioorg Med Chem;11:1663–8.

[9]   Tang L, Yu J, Leng Y, Feng Y, Yang Y, Ji R. 2003, Synthesis and insulin-sensitizing activity of a novel kind of benzopyran derivative. Bioorg Med Chem Lett;13:3437–40.

[10] Naghizadeh M, Taher MA, Abadi LZ, Moghaddam FH. 2017,  Synthesis, characterization and theoretical investigation of magnetite nanoclay modified as a new nanocomposite for simultaneous preconcentration of lead and nickel prior to ETAAS determination. Environ Nanotechnology, Monit Manag;7:46–56.

[11] Rahmati A, Khalesi Z. A 2012, one-pot, three-component synthesis of spiro [indoline-isoxazolo [4′, 3′: 5, 6] pyrido [2, 3-d] pyrimidine] triones in water. Tetrahedron;68:8472–9.

[12] Dömling 2006, A. Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem Rev;106:17–89.

[13] Tu SJ, Jiang H, Zhuang QY, Miao CB, Shi DQ, Wang XS, et al. 2003, One-pot synthesis of 2-amino-3-cyano-4-aryl-7, 7-dimethyl-5-oxo-5, 6, 7, 8-tetrahydro-4H-benzo [b] pyran under ultrasonic irradiation without catalyst. Chinese J Org Chem;23:488–90.

[14] Jin T-S, Wang A-Q, Shi F, Han L-S, Liu L-B, Li T-S. 2006, Hexadecyldimethyl benzyl ammonium bromide: an efficient catalystfor a clean one-pot synthesis of tetrahydrobenzopyran derivatives in water. Arkivoc;14:78–86.

[15] Balalaie S, Sheikh-Ahmadi M, Bararjanian M. 2007, Tetra-methyl ammonium hydroxide: An efficient and versatile catalyst for the one-pot synthesis of tetrahydrobenzo [b] pyran derivatives in aqueous media. Catal Commun;8:1724–8.

[16] Abdolmohammadi S, Balalaie S. 2007, Novel and efficient catalysts for the one-pot synthesis of 3, 4-dihydropyrano [c] chromene derivatives in aqueous media. Tetrahedron Lett;48:3299–303.

[17] Gao S, Tsai CH, Tseng C, Yao C-F. 2008, Fluoride ion catalyzed multicomponent reactions for efficient synthesis of 4H-chromene and N-arylquinoline derivatives in aqueous media. Tetrahedron;64:9143–9.

[18] Seifi M, Sheibani H. 2008, High surface area MgO as a highly effective heterogeneous base catalyst for three-component synthesis of tetrahydrobenzopyran and 3, 4-dihydropyrano [c] chromene derivatives in aqueous media. Catal Letters;126:275–9.

[19] Hekmatshoar R, Majedi S, Bakhtiari K. 2008, Sodium selenate catalyzed simple and efficient synthesis of tetrahydro benzo [b] pyran derivatives. Catal Commun;9:307–10.

[20] Ren Y-M, Cai C. 2008, Convenient and efficient method for synthesis of substituted 2-amino-2-chromenes using catalytic amount of iodine and K2CO3 in aqueous medium. Catal Commun;9:1017–20.

[21] Heravi MM, Jani BA, Derikvand F, Bamoharram FF, Oskooie HA. 2008, Three component, one-pot synthesis of dihydropyrano [3, 2-c] chromene derivatives in the presence of    H6P2W18O62·18H2O as a green and recyclable catalyst. Catal Commun;10:272–5.

[22] Khurana JM, Kumar S. 2009, Tetrabutylammonium bromide (TBAB): a neutral and efficient catalyst for the synthesis of biscoumarin and 3, 4-dihydropyrano [c] chromene derivatives in water and solvent-free conditions. Tetrahedron Lett;50:4125–7.

[23] Sabitha G, Arundhathi K, Sudhakar K, Sastry BS, Yadav JS. 2009, Cerium (III) chloride–catalyzed one-pot synthesis of tetrahydrobenzo [b] pyrans. Synth Commun;39:433–42.

[24] Stadelman WJ. 2000, Eggs and egg products. Encyclopedia of Food Science and Technology; Wiley and sons, Newyork.

[25] Mezenner NY, Bensmaili A., 2009, Kinetics and thermodynamic study of phosphate adsorption on iron hydroxide-eggshell waste. Chemical Engineering Journal;147:87–96.

[26] Wei Z, Xu C, Li B. 2009; Application of waste eggshell as low-cost solid catalyst for biodiesel production. Bioresour Technol;100:2883–5.

[27] Yoo S, Hsieh JS, Zou P, Kokoszka J. 2009; Utilization of calcium carbonate particles from eggshell waste as coating pigments for ink-jet printing paper. Bioresource Technology;100:6416–21.

[28] Eisa WH, Abdel-Moneam YK, Shaaban Y, Abdel-Fattah AA, Zeid AMA. 2011, Gamma-irradiation assisted seeded growth of Ag nanoparticles within PVA matrix. Mater Chem Phys;128:109–13.

[29] Yang D, Qi L, Ma J. 2002, Eggshell membrane templating of hierarchically ordered macroporous networks composed of TiO2 tubes. Adv Mater;14:1543–6.

[30] Fan T-X, Chow S-K, Zhang D. 2009, Biomorphic mineralization: from biology to materials. Prog Mater Sci;54:542–659.

[31] Zhang W, Zhang D, Fan T, Gu J, Ding J, Wang H, et al. 2008, Novel photoanode structure templated from butterfly wing scales. Chem Mater;21:33–40.

[32] Valtchev V, Gao F, Tosheva L., 2008, Porous materials via egg-constituents templating. New J Chem;32:1331–7.

[33] Tsai W-T, Hsien K-J, Hsu H-C, Lin C-M, Lin K-Y, Chiu C-H. 2008, Utilization of ground eggshell waste as an adsorbent for the removal of dyes from aqueous solution. Bioresour Technol;99:1623–9.

[34] Liao D, Zheng W, Li X, Yang Q, Yue X, Guo L, et al. 2010, Removal of lead (II) from aqueous solutions using carbonate hydroxyapatite extracted from eggshell waste. J Hazard Mater;177:126–30.

[35] Viriya-Empikul N, Krasae P, Puttasawat B, Yoosuk B, 2010, Chollacoop N, Faungnawakij K. Waste shells of mollusk and egg as biodiesel production catalysts. Bioresour Technol;101:3765–7.

[36] Sharma YC, Singh B, Korstad J. 2010, Application of an efficient nonconventional heterogeneous catalyst for biodiesel synthesis from Pongamia pinnata oil. Energy & Fuels;24:3223–31.

[37] Afshar EA, Taher MA, Fazelirad H, Naghizadeh M. 2017, Application of dispersive liquid–liquid–solidified floating organic drop microextraction and ETAAS for the preconcentration and determination of indium. Anal Bioanal Chem;409:1837–43.

[38] Gao Y, Xu C. 2012, Synthesis of dimethyl carbonate over waste eggshell catalyst. Catal Today;190:107–11.

[39] Montilla A, Del Castillo MD, Sanz ML, Olano A. 2005, Egg shell as catalyst of lactose isomerisation to lactulose. Food Chem;90:883–90.

[40] Cai W, Wan J. 2007, Facile synthesis of superparamagnetic magnetite nanoparticles in liquid polyols. J Colloid Interface Sci;305:366–70.

[41] Veisi H, Mohammadi P, Gholami J. 2014, Sulfamic acid heterogenized on functionalized magnetic Fe3O4 nanoparticles with diaminoglyoxime as a green, efficient and reusable catalyst for one‐pot synthesis of substituted pyrroles in aqueous phase. Appl Organomet Chem;28:868–73.

[42] Yan F, Li J, Zhang J, Liu F, Yang W. 2009, Preparation of Fe3O4/polystyrene composite particles from monolayer oleic acid modified Fe3O4 nanoparticles via miniemulsion polymerization. J Nanoparticle Res;11:289–96.

[43] Gu S, Onishi J, Kobayashi Y, Nagao D, Konno M. 2005, Preparation and colloidal stability of monodisperse magnetic polymer particles. J Colloid Interface Sci;289:419–26.

[44] Wang X, Ji H, Zhang X, Zhang H, Yang X. 2010, Hollow polymer microspheres containing a gold nanocolloid core adsorbed on the inner surface as a catalytic microreactor. J Mater Sci;45:3981–9.

[45] Liao Z, Wang H, Lv R, Zhao P, Sun X, Wang S, et al. 2011, Polymeric liposomes-coated superparamagnetic iron oxide nanoparticles as contrast agent for targeted magnetic resonance imaging of cancer cells. Langmuir;27:3100–5.

[46] Naghizadeh M, Taher MA, Behzadi M, Moghaddam FH. 2015, Simultaneous preconcentration of bismuth and lead ions on modified magnetic core–shell nanoparticles and their determination by ETAAS. Chem Eng J;281:444–52.

[47] Koch CC. 2002, Nanostructured Materials: Processing. Prop Potential Appl Taylor Fr.

[48] Nakayama H, Arakaki A, Maruyama K, Takeyama H, Matsunaga T. 2003, Single‐nucleotide polymorphism analysis using fluorescence resonance energy transfer between DNA‐labeling fluorophore, fluorescein isothiocyanate, and DNA intercalator, POPO‐3, on bacterial magnetic particles. Biotechnol Bioeng;84:96–102.

[49] Jia H, Zhu G, Wang P. 2003, Catalytic behaviors of enzymes attached to nanoparticles: the effect of particle mobility. Biotechnol Bioeng;84:406–14.

[50] Engin B, Demirtaş H, Eken M. 2006, Temperature effects on egg shells investigated by XRD, IR and ESR techniques. Radiat Phys Chem;75:268–77.