Synthesis of Nano ZnO: A Catalyst for N-formylation of Aromatic Amines and Biodiesel Application

Author(s): Lakshmi S.R. Yadav, Rangashamaiah Venkatesh, Mahadevaiah Raghavendra, Thippeswamy Ramakrishnappa, Narayanappa Dhananjaya, Ganganagappa Nagaraju*

Journal Name: Current Nanomaterials

Volume 5 , Issue 1 , 2020


Become EABM
Become Reviewer
Call for Editor

Graphical Abstract:


Abstract:

Background: Zinc oxide nanoparticles prepared from an easy, eco-friendly and cost-effective green combustion technique using an extract of turmeric root has been an immense attractive nanomaterial that is used widely in light emitting display systems, piezoeletricity, electric conductivity, and biological applications. The prepared samples were characterized for their structural and morphological study using various analytical techniques.

Results: Crystallite size was calculated by both XRD as well as UV-visible absorption measurements and Crystallite size was found to be 14-36 nm. An equation was developed with the aid of an effective mass model (Brus 1986) to calculate the size of the particle as a function of the peak absorbance wavelength. The energy bandgap of the synthesized sample calculated to be in the range of 4.74 - 5.0 eV by UV-Vis spectra confirms the quantum confinement. ZnO nanocatalyst is used for the synthesis of biodiesel from garcinia gummigutta seed oil has been studied. The environmental friendly procedure was carried for the formylation of amines under solvent-free reaction condition and simple work-up giving pure products with prompt recyclability behavior are the main features of the reaction.

Conclusion: In this work, ZnO NPs were synthesised using turmeric root extract as a fuel via green combustion method. It is an environmentally friendly, easy as well as cost-effective method for the synthesis of nanoparticles. ZnO NPs were examined through various equipments such as PXRD, UV-Vis, FTIR, and SEM studies. XRD study show the hexagonal wurtzite structure. it is a good catalyst for the synthesis of biodiesel from the pongamiapinnata oil. It also serves as a catalyst for the Nformylation reactions, which involves the clean procedure under milder reaction conditions with an excellent yield of the desired products.

Keywords: ZnO Nps, SEM, photoluminescence, biodiesel, formylation, aromatic amines.

[1]
Nunes P, Fernandes B, Fortunato E, Vilarinho P, Martins R. Performances presented by zinc oxide thin films deposited by spray pyrolysis. Thin Solid Films 1999; 337(1-2): 176-9.
[http://dx.doi.org/10.1016/S0040-6090(98)01394-7]
[2]
Chopra L, Major S, Pandya DK, Rastogi RS, Vankar VD. Thermal device applications. Thin Solid Films 1983; 1021: 1-4.
[http://dx.doi.org/10.1016/0040-6090(83)90256-0]
[3]
Yadav RLS, Lingaraju K, Nagaraju G. Electrochemical sensing, photocatalytic and biological activities of zno nanoparticles: synthesis via green chemistry route. Int J Nanosci 2016; 15(2): 165-175. films for organic light-emitting devices. Appl Phys Lett 2000; 76(3): 259-61.
[4]
Chen Y, Bagnall D, Yao T. ZnO as a novel photonic material for the UV region. Mater Sci Eng B 2000; 75(2-3): 190-8.
[http://dx.doi.org/10.1016/S0921-5107(00)00372-X]
[5]
Zhang DH, Xue ZY, Wang QP. The mechanisms of blue emission from ZnO films deposited on glass substrate by rf magnetron sputtering. J Phys D Appl Phys 2002; 35(21): 2837.
[http://dx.doi.org/10.1088/0022-3727/35/21/321]
[6]
Yadav LR, Raghavendra M, Manjunath K, Nagaraju G. Photocatalytic, biodiesel, electrochemical sensing properties and formylation reactions of ZnO nanoparticles synthesized via eco-friendly green synthesis method. J Mater Sci Mater Electron 2018; 29(10): 8747-59.
[http://dx.doi.org/10.1007/s10854-018-8891-9]
[7]
Matsunaga T, Okamura Y, Tanaka T. Biotechnological application of nano-scale engineered bacterial magnetic particles. J Mater Chem 2004; 14(14): 2099-105.
[http://dx.doi.org/10.1039/b404844j]
[8]
Matsunaga T, Suzuki T, Tanaka M, Arakaki A. Molecular analysis of magnetotactic bacteria and development of functional bacterial magnetic particles for nano-biotechnology. Trends Biotechnol 2007; 25(4): 182-8.
[http://dx.doi.org/10.1016/j.tibtech.2007.02.002] [PMID: 17306901]
[9]
Mornet S, Vasseur S, Grasset F, Duguet E. Magnetic nanoparticle design for medical diagnosis and therapy. J Mater Chem 2004; 14(14): 2161-75.
[http://dx.doi.org/10.1039/b402025a]
[10]
Millstone JE, Hurst SJ, Métraux GS, Cutler JI, Mirkin CA. Colloidal gold and silver triangular nanoprisms. Small 2009; 205(6): 646-64.
[11]
Na HB, Song IC, Hyeon T. Inorganic nanoparticles for MRI contrast agents. Adv Mater 2009; 21(21): 2133-48.
[http://dx.doi.org/10.1002/adma.200802366]
[12]
Niederberger M. Nonaqueous sol-gel routes to metal oxide nanoparticles. Acc Chem Res 2007; 40(9): 793-800.
[http://dx.doi.org/10.1021/ar600035e] [PMID: 17461544]
[13]
Pinna N, Niederberger M. Surfactant-free nonaqueous synthesis of metal oxide nanostructures. Angew Chem Int Ed Engl 2008; 47(29): 5292-304.
[http://dx.doi.org/10.1002/anie.200704541] [PMID: 18561355]
[14]
Yin YT, Wu SH, Chen CH, Chen LY. Fabrication of ZnO nanorods in one pot via solvothermal method. J Chin Chem Soc (Taipei) 2011; 58(6): 749-55.
[http://dx.doi.org/10.1002/jccs.201190117]
[15]
Abrishami ME, Kompany A. Preparation of ZnO nanoparticles by surfactant-assisted complex sol-gel using zinc nitrate. J Sol-Gel Sci Technol 2012; 62: 153-9.
[16]
Chowdhury S, Kuen-Song L. Synthesis and characterization of 1D ceria nanomaterials for CO oxidation and steam reforming of methanol. J Nanomater 2011; 157690: 1-16.
[http://dx.doi.org/10.1155/2011/157690]
[17]
Soliman NK. Factors affecting CO oxidation reaction over nanosized materials: a review. J Mater Res Technol 2019; 8: 2345-407.
[http://dx.doi.org/10.1016/j.jmrt.2018.12.012]
[18]
Barreca D, Comini E, Gasparotto A, et al. CeO2 nanoparticles synthesized by a microwave-assisted hydrothermal method: evolution from nanospheres to nanorods. J Nanosci Nanotechnol 2008; 8: 1012-6.
[http://dx.doi.org/10.1166/jnn.2008.080] [PMID: 18464442]
[19]
Reddy Yadav LS, Lingaraju K, Nagaraju G. Antibacterial and photocatalytic activities of ZnO nanoparticles: synthesized using watermelon juice as fuel. Int J Nanosci 2015; 15: 155-61.
[20]
Nigro RL, Toro R, Malandrin G, Fragal IL. CeO2 nanoparticles synthesized by a microwave-assisted hydrothermal method: evolution from nanospheres to nanorods. Chem Mater 2003; 15: 1434-40.
[21]
Green TW, Wuts PGM. Protective groups in organic synthesis. New York: Wiley-Interscience 1999.
[http://dx.doi.org/10.1002/0471220574]
[22]
Reddy Yadav LS, Nagaraju G, Dhananjaya N. Biosynthesised ZnO: Dy3+ nanoparticles: biodiesel properties and reusable catalyst for N-formylation of aromatic amines with formic acid. Eur Phys J Plus 2018; 133: 153-62.
[http://dx.doi.org/10.1140/epjp/i2018-11963-6]
[23]
Kakehi A, Ito S, Hayashi S. Preparation of new nitrogen-bridged heterocycles. Bull Chem Soc Jpn 1995; 68: 3573-80.
[http://dx.doi.org/10.1246/bcsj.68.3573]
[24]
Waki J, Meienhofer J. Efficient preparation of N alpha-formylamino acid tert-butyl esters. J Org Chem 1977; 42: 2019-20.
[25]
Yuya O. Lewis base catalysed asymmetric reactions involving hypervalent silicate intermediates. Synthesis 2006; 09: 1391-401.
[26]
Mitsuo K. Hyper coordinate silicon species in organic syntheses.. Akiba K. Chemistry of hypervalent compounds. United States: Wiley 1999.
[27]
Sudarshan NS, Narendra N, Hemantha HP, Sureshbabu VV. An efficient conversion of the carboxylic group of N-Fmoc α-amino acids/peptide acids into N-formamides employing isocyanates as key intermediates. J Org Chem 2007; 72(25): 9804-7.
[http://dx.doi.org/10.1021/jo701371k] [PMID: 17999520]
[28]
Kim GJ. Solvent-free zinc-catalysed amine N-formylation. Bull Korean Chem Soc 2010; 31: 2989-91.
[http://dx.doi.org/10.5012/bkcs.2010.31.10.2989]
[29]
Strazzoline P, Giumanini AG, Cauci S. Acetic formic anhydride a review. Tetrahedron 1990; 46: 1081-118.
[http://dx.doi.org/10.1016/S0040-4020(01)86676-X]
[30]
Hao L. Imidazolium-based ionic liquids catalyzed formylation of amines using carbon dioxide and phenylsilane at room temperature. ACS Catal 2015; 5: 4989-93.
[http://dx.doi.org/10.1021/acscatal.5b01274]
[31]
Sajadi SM, Maham M. An eco-friendly N-formylation of amines using nano cerium oxide as a recyclable catalyst under solvent-free and ultrasound irradiation conditions at room temperature. Lett Org Chem 2014; 11: 49-54.
[http://dx.doi.org/10.2174/157017861131000057]
[32]
Hill DR, Hsiao CN, Kurukulasuriya R, Wittenberger SJ. 2,2,2-trifluoroethyl formate: a versatile and selective reagent for the formylation of alcohols, amines, and N-hydroxylamines. Org Lett 2002; 4(1): 111-3.
[http://dx.doi.org/10.1021/ol016976d] [PMID: 11772103]
[33]
Blicke FF, Lu CJJ. Formylation of amines with chloral and reduction of the N-formyl derivatives with lithium aluminium hydride. J Am Chem Soc 1952; 74: 3933-44.
[http://dx.doi.org/10.1021/ja01135a503]
[34]
Yatish KV, Lalithamba HS, Suresh R. Optimization of scum oil biodiesel production by using response surface methodology. Prod Safety Environ Prot 2016; 102: 667-72.
[35]
Venkatesh R, Pratibha S, Dhananjaya N. Study of optical and dielectric properties of alkali metal cation (Li+, Na+, K+) co-doped Eu3+ activated gadolinium aluminate nanoparticles. Mater Res Express 2019; 6: 095008-15.
[http://dx.doi.org/10.1088/2053-1591/ab268b]
[36]
Pesika NS, Stebe KJ. Determination of the particle size distribution of quantum nanocrystals from absorbance spectra. Adv Mater 2003; 15: 1289-91.
[http://dx.doi.org/10.1002/adma.200304904]
[37]
Djurišić AB, Chen XY. ZnO nanostructures for optoelectronics: material properties and device applications. Prog Quant Electron 2010; 34: 191-259.
[38]
Chakraborty S, Ganguli D, Chaudhuri S. Photoluminescence of ZnO nanocrystallites confined in sol-gel silica matrix. J Phys D Appl Phys 2003; 36: 146-51.
[http://dx.doi.org/10.1088/0022-3727/36/2/311]
[39]
Lathika Devi SK, Sudarsanakumar K. Wavelength tunable photoluminescence of ZnO/porous Si nanocomposites. J Lumin 2010; 130: 12-22.
[40]
Zhou H, Alves H, Hofman DM. Reproducible resistance switching characteristics of pulsed laser deposited polycrystalline Nb2O5. Appl Phys Lett 2002; 80: 210-5.
[http://dx.doi.org/10.1063/1.1432763]
[41]
Venkatesh R, Dhananjaya N. Effect of Li, Na, K cations on photoluminescence of GdAlO3:Eu3+ nanophosphor and study of Li cation on its antimicrobial activity. J Alloys Compd 2018; 732: 725-39.
[http://dx.doi.org/10.1016/j.jallcom.2017.10.117]


Rights & PermissionsPrintExport Cite as

Article Details

VOLUME: 5
ISSUE: 1
Year: 2020
Page: [66 - 78]
Pages: 13
DOI: 10.2174/2405461505666200316121735
Price: $65

Article Metrics

PDF: 23
HTML: 1