Synthesis and Characterization of GO-Chit-Ni Nanocomposite as a Recoverable Nanocatalyst for Reducing Nitroarenes in Water

Author(s): Mosayeb Sarvestani, Roya Azadi*

Journal Name: Letters in Organic Chemistry

Volume 17 , Issue 7 , 2020

Become EABM
Become Reviewer

Graphical Abstract:


Abstract:

In the present study, nickel nanoparticles (Ni-NPs) immobilized on graphene oxide-chitosan (GO-Chit-Ni) have been synthesized and characterized as a catalyst for reduction of nitroarenes in water. For this purpose, GO has been functionalized with chitosan (GO-Chit). Then, Ni-NPs were immobilized on the surface of GO-Chit using a simple method. The GO-Chi-Ni nanocomposites were characterized using Fourier Transforms Infrared Spectroscopy (FT-IR), Transmission Electron Microscopy (TEM), X-Ray Diffraction Measurements (XRD), and Atomic Adsorption Spectrometry (AAS). The GO-Chi-Ni nanoparticles demonstrated appropriate catalytic activity in reducing nitroarenes to aryl amines in the existence of sodium borohydride (NaBH4) aqueous solution as a hydrogen source at 80oC. This catalytic system applies environmentally benign water as a solvent that is cheap, easily accessible, non-toxic, non-volatile, non-flammable and thermally stable. This type of catalyst can be applied several times with no considerable change in its performance.

Keywords: Graphene oxide, Chitosan, Nickel nanoparticles, Nitroarene, Reduction, Aryl amine

[1]
Luo, P.; Xu, K.; Zhang, R.; Huang, L.; Wang, J.; Xing, W. J. Catal. Sci. Technol., 2012, 2, 301-304.
[http://dx.doi.org/10.1039/C1CY00358E]
[2]
Blaser, H.; Steiner, H.; Studer, M. ChemCatChem, 2009, 1, 210-221.
[http://dx.doi.org/10.1002/cctc.200900129]
[3]
Serna, P.; Corma, A. ACS Catal., 2015, 5, 7114-7121.
[http://dx.doi.org/10.1021/acscatal.5b01846]
[4]
Jagadeesh, R.V.; Surkus, A.E.; Junge, H.; Pohl, M.M.; Radnik, J.; Rabeah, J.; Huan, H.; Schünemann, V.; Brückner, A.; Beller, M. Science, 2013, 342(6162), 1073-1076.
[http://dx.doi.org/10.1126/science.1242005] [PMID: 24288327]
[5]
Liu, X.; Ye, S.; Li, H.Q.; Liu, M.Y.; Cao, Y.; Fan, K.N. Catal. Sci. Technol., 2013, 3, 3200-3206.
[http://dx.doi.org/10.1039/c3cy00533j]
[6]
Kim, J.H.; Park, J.H.; Chung, Y.K.; Park, K.H. Adv. Synth. Catal., 2012, 354, 2412-2418.
[http://dx.doi.org/10.1002/adsc.201200356]
[7]
Johnson, J.A.; Makis, J.J.; Marvin, K.A.; Rodenbusch, S.E.; Stevenson, K.J. J. Phys. Chem. C, 2013, 117, 22644-22651.
[http://dx.doi.org/10.1021/jp4041474]
[8]
Ma, H.; Wang, H.; Na, C. Appl. Catal. B, 2015, 163, 198-204.
[http://dx.doi.org/10.1016/j.apcatb.2014.07.062]
[9]
Furukawa, S.; Takahashi, K.; Komatsu, T. Chem. Sci. (Camb.), 2016, 7, 4476-4484.
[http://dx.doi.org/10.1039/C6SC00817H]
[10]
Shimizu, K.I.; Miyamoto, Y.; Satsuma, A. J. Catal., 2010, 270, 86-94.
[http://dx.doi.org/10.1016/j.jcat.2009.12.009]
[11]
Dey, R.; Mukherjee, N.; Ahammed, S.; Ranu, B.C. Chem. Commun. (Camb.), 2012, 48(64), 7982-7984.
[http://dx.doi.org/10.1039/c2cc30999h] [PMID: 22531391]
[12]
(a) Ajmal, M.; Siddiq, M.; Al-Lohedan, H.; Sahiner, N. RSC Advances, 2014, 4, 59562-59570.
[http://dx.doi.org/10.1039/C4RA11667D]
(b) Gao, W.Z.; Xu, Y.; Chen, Y.; Fu, W.F. Chem. Commun. (Camb.), 2015, 51(67), 13217-13220.
[http://dx.doi.org/10.1039/C5CC04030B] [PMID: 26193992]
(c) Liu, H.; Deng, J.; Li, W. Catal. Lett., 2010, 137, 261-266.
[http://dx.doi.org/10.1007/s10562-010-0362-8]
(d) Ji, Z.; Shen, X.; Zhu, G.; Zhou, H.; Yuan, A. J. Mater. Chem.,2012, 22, 471-3477.eTian, Y.; Liu, Y.; Pang, F.; Wang, F.; Zhang, X. Colloids Surf. A Physicochem. Eng. Asp., 2015, 464, 96-103.
[http://dx.doi.org/10.1016/j.colsurfa.2014.10.027]
[13]
Vernekar, A.A.; Patil, S.; Bhat, C.; Tilve, S.G. RSC Advances, 2013, 3, 13243-13250.
[http://dx.doi.org/10.1039/c3ra41090k]
[14]
Kadam, H.K.; Tilve, S.G. RSC Advances, 2012, 2, 6057-6060.
[http://dx.doi.org/10.1039/c2ra20371e]
[15]
(a) Shi, Q.F.; Diao, G.W. Electrochim. Acta, 2011, 58, 399-405.
[http://dx.doi.org/10.1016/j.electacta.2011.09.064]
(b) Sua, Y.X.; Fan, B.X.; Wang, L.S.; Liu, Y.F.; Huang, B.C.; Fu, M.L.; Chen, L.M.; Ye, D.Q. Catal. Today, 2013, 201, 115-121.
[http://dx.doi.org/10.1016/j.cattod.2012.04.063]
(c) Yuan, C.; Xu, Y.; Luo, W.; Zeng, B.; Qiu, W.; Liu, J.; Huang, H.; Dai, L. Nanotechnology, 2012, 23(17), 175301-175309.
[http://dx.doi.org/10.1088/0957-4484/23/17/175301] [PMID: 22481383]
[16]
(a) Horacek, J.; Stavova, G.; Kelbichova, V.; Kubicka, D. Catal. Today, 2013, 204, 38-45.
[http://dx.doi.org/10.1016/j.cattod.2012.08.015]
(b) Yoshida, A.; Mori, Y.; Ikeda, T.; Azemoto, K.; Naito, S. Catal. Today, 2013, 203, 153-157.
[http://dx.doi.org/10.1016/j.cattod.2012.04.020]
[17]
Kim, Y.S.; Milner, J.A. J. Nutr. Biochem., 2005, 16(2), 65-73.
[http://dx.doi.org/10.1016/j.jnutbio.2004.10.007] [PMID: 15681163]
[18]
Li, P.; Song, Y.; Liu, Ch.; Li, X.; Zhou, G.; Fan, Y. Mater. Lett., 2014, 114, 132-135.
[http://dx.doi.org/10.1016/j.matlet.2013.09.111]
[19]
(a) Lou, M.M.; Zhu, B.; Muhammad, I.; Li, B.; Xie, G.L.; Wang, Y.L.; Li, H.Y.; Sun, G.C. Carbohydr. Res., 2011, 346(11), 1294-1301.
[http://dx.doi.org/10.1016/j.carres.2011.04.042] [PMID: 21605851]
(b) Liu, L.; Li, C.; Bao, C.; Jia, Q.; Xiao, P.; Liu, X.; Zhang, Q. Talanta, 2012, 93, 350-357.
[http://dx.doi.org/10.1016/j.talanta.2012.02.051] [PMID: 22483922]
[20]
Rivas-Araiza, R.; Alcouffe, P.; Rochas, C.; Montembault, A.; David, L. Langmuir, 2010, 26(22), 17495-17504.
[http://dx.doi.org/10.1021/la102907u] [PMID: 20879755]
[21]
Elwakeel, K.Z.; Disper, J. Sci. Technol., 2010, 31, 273-288.
[22]
Park, J.H.; Saravanakumar, G.; Kim, K.; Kwon, I.C. Adv. Drug Deliv. Rev., 2010, 62(1), 28-41.
[http://dx.doi.org/10.1016/j.addr.2009.10.003] [PMID: 19874862]
[23]
Cotugno, P.; Casiello, M.; Nacci, A.; Mastrorilli, P.; Dell’Anna, M.M.; Monopoli, A. J. Organomet. Chem., 2014, 752, 1-5.
[http://dx.doi.org/10.1016/j.jorganchem.2013.11.033]
[24]
Gioia, C.; Ricci, A.; Bernardi, L.; Bourahla, K.; Tanchoux, N.; Robitzer, M.; Quignard, F. Eur. J. Org. Chem., 2013, 2013, 588-594.
[http://dx.doi.org/10.1002/ejoc.201201187]
[25]
(a) Lipshutz, B.H.; Ghorai, S.; Cortes-Clerget, M. Chemistry, 2018, 24(26), 6672-6695.
[http://dx.doi.org/10.1002/chem.201705499] [PMID: 29465785]
(b) Simon, M.O.; Li, C.J. Chem. Soc. Rev., 2012, 41, 1415-1427.
[http://dx.doi.org/10.1039/C1CS15222J]
[26]
(a) Guo, W.; Wu, B.; Zhou, X.; Chen, P.; Wang, X.; Zhou, Y.G.; Liu, Y.; Li, C. Angew. Chem. Int. Ed., 2015, 54, 4522-4526.
[http://dx.doi.org/10.1002/anie.201409894]
(b) Li, Y.; Huang, Y.; Gui, Y.; Sun, J.; Li, J.; Zha, Z. Z. Org. Lett., 2017, 19, 6416-6419.
[http://dx.doi.org/10.1021/acs.orglett.7b03299]
[27]
Álvarez, M.; Gava, R.; Rodríguez, M.R.; Rull, S.G.; Pérez, P.J. ACS Catal., 2017, 7, 3707-3711.
[http://dx.doi.org/10.1021/acscatal.6b03669]
[28]
Liu, K.J.; Fu, Y.L.; Xie, L.Y.; Wu, C.; He, W.B.; Peng, S.; Wang, Z.; Bao, W.H.; Cao, Z.; Xu, X.; He, W.M. ACS Sustain. Chem.& Eng., 2018, 6, 4916-4921.
[http://dx.doi.org/10.1021/acssuschemeng.7b04400]
[29]
Wu, C.; Xin, X.; Fu, Z.M.; Xie, L.Y.; Liu, K.J.; Wang, Z.; Li, W.; Yuan, Z.H.; He, W.M. Green Chem., 2017, 19, 1983-1989.
[http://dx.doi.org/10.1039/C7GC00283A]
[30]
Tang, L.; Yang, Y.; Wen, L.; Yang, X.; Wang, Z. Green Chem., 2016, 18, 1224-1228.
[http://dx.doi.org/10.1039/C5GC02755A]
[31]
Lin, Y.M.; Lu, G.P.; Wang, G.X.; Yi, W.B. J. Org. Chem., 2017, 82(1), 382-389.
[http://dx.doi.org/10.1021/acs.joc.6b02459] [PMID: 27936696]
[32]
Yang, J.; Mei, F.; Fu, S.; Gu, Y. Green Chem., 2018, 20, 1367-1374.
[http://dx.doi.org/10.1039/C7GC03644B]
[33]
(a) Dreyer, D.R.; Park, S.; Bielawski, C.W.; Ruoff, R.S. Chem. Soc. Rev., 2010, 39(1), 228-240.
[http://dx.doi.org/10.1039/B917103G] [PMID: 20023850]
(b) Tan, R.; Li, C.; Luo, J.; Kong, Y.; Zheng, W.; Yin, D. J. Catal., 2013, 298, 138-147.
[http://dx.doi.org/10.1016/j.jcat.2012.11.024]
[34]
Depan, D.; Girase, B.; Shah, J.S.; Misra, R.D.K. Acta Biomater., 2011, 7(9), 3432-3445.
[http://dx.doi.org/10.1016/j.actbio.2011.05.019] [PMID: 21664303]
[35]
(a) Sarvestani, M.; Azadi, R. Appl. Organomet. Chem., 2017, 31, e3667
[http://dx.doi.org/10.1002/aoc.3667]
(b) Sarvestani, M.; Azadi, R. Appl. Organomet. Chem., 2018, 32, e3906
[http://dx.doi.org/10.1002/aoc.3906]
(c) Sarvestani, M.; Azadi, R. Can. J. Chem., 2019, 97, 191-196.
[http://dx.doi.org/10.1139/cjc-2018-0011]
[36]
Rajesh, R.; Sujanthi, E.; Senthil Kumar, S.; Venkatesan, R. Phys. Chem. Chem. Phys., 2015, 17(17), 11329-11340.
[http://dx.doi.org/10.1039/C5CP00682A] [PMID: 25845989]
[37]
Wang, J.; Yuan, Zh.; Nie, R.; Hou, Zh.; Zheng, X. Ind. Eng. Chem. Res., 2010, 49, 4664-4669.
[http://dx.doi.org/10.1021/ie1002069]
[38]
Hummers, W.S.; Offeman, R.E. J. Am. Chem. Soc., 1958, 80, 1339-1339.
[http://dx.doi.org/10.1021/ja01539a017]
[39]
Rai, R.K.; Mahata, A.; Mukhopadhyay, S.; Gupta, S.; Li, P.Z.; Nguyen, K.T.; Zhao, Y.; Pathak, B.; Singh, S.K. Inorg. Chem., 2014, 53(6), 2904-2909.
[http://dx.doi.org/10.1021/ic402674z] [PMID: 24564248]


Rights & PermissionsPrintExport Cite as

Article Details

VOLUME: 17
ISSUE: 7
Year: 2020
Page: [523 - 531]
Pages: 9
DOI: 10.2174/1570178616666190806125217
Price: $65

Article Metrics

PDF: 18
HTML: 1