Abstract
A magnetic nanostructured catalyst (Fe3O4@SiO2-Amp-Rh) modified with 2-(aminomethyl)phenols (Amp) was designed and prepared, which is used to catalyze the reduction of aromatic nitro compounds into corresponding amines and the degradation of dyes. The 2-aminomethylphenol motif plays a vital role in the immobilization of rhodium nanoparticles to offer extraordinary stability, which has been characterized by using various techniques, including transmission electron microscopy (TEM), thermal gravimetric analyzer (TGA), X-Ray Diffraction (XRD), and X-ray photoelectron spectroscopy (XPS). A variety of nitroaromatic derivatives have been reduced to the corresponding anilines in water with up to yields of 99% within 1 h at room temperature. In addition, the catalyst system is effective in catalyzing the reduction of toxic pollutant 4-nitrophenol and the degradation of MO, MB and RhB dyes. Importantly, this catalyst Fe3O4@SiO2-Amp-Rh can be easily recovered by an external magnetic field because of the presence of magnetic core of Fe3O4, and the activity of Fe3O4@SiO2-Amp-Rh does not decrease significantly after 7 times’ recycling, which indicates that the catalyst performed high reactivity as well as stability.
Graphical abstract
![](http://media.springernature.com/lw685/springer-static/image/art%3A10.1007%2Fs10562-021-03688-4/MediaObjects/10562_2021_3688_Figa_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs10562-021-03688-4/MediaObjects/10562_2021_3688_Fig1_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs10562-021-03688-4/MediaObjects/10562_2021_3688_Fig2_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs10562-021-03688-4/MediaObjects/10562_2021_3688_Fig3_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs10562-021-03688-4/MediaObjects/10562_2021_3688_Fig4_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs10562-021-03688-4/MediaObjects/10562_2021_3688_Fig5_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs10562-021-03688-4/MediaObjects/10562_2021_3688_Fig6_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs10562-021-03688-4/MediaObjects/10562_2021_3688_Fig7_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs10562-021-03688-4/MediaObjects/10562_2021_3688_Fig8_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs10562-021-03688-4/MediaObjects/10562_2021_3688_Fig9_HTML.png)
Similar content being viewed by others
References
Farooqi ZH, Naseem K, Ijaz A, Begum R (2016) J Polym Eng 36:87
Begum R, Naseem K, Ahmed E, Sharif A, Farooqi ZH (2016) Colloid Surf A-Physicochem Eng Asp 511:17
Layek K, Kantam ML, Shirai M, Nishio-Hamane D, Sasaki T, Maheswaran H (2012) Green Chem 14:3164
Lauwiner M, Rys P, Wissmann J (1998) Appl Catal A-Gen 172:141
Ayad MM, Amer WA, Kotp MG (2017) Mol Catal 439:72
Westerhaus FA, Jagadeesh RV, Wienhöfer G, Pohl MM, Radnik J, Surkus AE, Beller M (2013) Nat Chem 5:537
Wang L, Guan E, Zhang J, Yang J, Zhu Y, Han Y, Xiao FS (2018) Nat Commun 9:1362
Wei H, Liu X, Wang A, Zhang L, Qiao B, Yang X, Zhang T (2014) Nat Commun 5:5634
Datta KJ, Rathi AK, Kumar P, Kaslik J, Medrik I, Ranc V, Gawande MB (2017) Sci Rep 7:11585
Wang D, Astruc D (2018) Chem Rev 115:6621
Shokouhimehr M, Nasrollahzadeh M (2019) Appl Sci 9:4183
Zhou J, Li Y, Sun H, Tang Z, Qi L, Liu L, Liang Q (2017) Green Chem 19:3400
Byun S, Song Y, Kim BM (2016) ACS Appl Mater Interfaces 8:14637
Lou XB, He L, Qian L, Liu YM, Cao Y, Fan KN (2011) Adv Synth Catal 353:281
Porwal D, Oestreich M (2016) Eur J Org Chem 2016:3307
Zhang X, Shang N, Zhou X, Feng C, Gao S, Wu Q, Wang C (2017) New J Chem 41:3443
Mei Y, Lu Y, Polzer F, Ballauff M, Drechsler M (2007) Chem Mat 19:1062
Junge K, Schröder K, Beller M (2011) Chem Commun 47:4849
Jia WG, Zhang H, Zhang T, Xie D, Ling S, Sheng EH (2016) Organometallics 35:503
Copéret C, Basset JM (2007) Adv Synth Catal 349:78
Baran T (2020) Carbohydr Polym 237:116105
Trindade AF, Gois PMP, Afonso CAM (2009) Chem Rev 109:418
Karimi B, Mansouri F, Mirzaei HM (2015) ChemCatChem 7:1736
Appaturi JN, Johan MR, Ramalingam RJ, Al-Lohedan HA (2018) Microporous Mesoporous Mat 256:67
Kalidindi SB, Jagirdar BR (2011) Chemsuschem 5:65
Yuan X, Wang Z, Zhang Q, Luo J (2019) RSC Adv 9:23614
Deng YH, Wang CC, Hu JH, Yang WL, Fu SK (2005) Colloid Surf A-Physicochem Eng Asp 262:87
Cardellicchio C, Ciccarella G, Naso F, Perna F, Tortorella P (1999) Tetrahedron 55:14685
Wen H, Yao K, Zhang Y, Zhou Z, Kirschning A (2009) Catal Commun 10:1207
Rai RK, Mahata A, Mukhopadhyay S, Gupta S, Li PZ, Nguyen KT, Singh SK (2014) Inorg Chem 53:2904
Sun H, Ai Y, Li D, Tang Z, Shao Z, Liang Q (2017) Chem Eng J 314:328
Gkizis PL, Stratakis M, Lykakis IN (2013) Catal Commun 36:48
Guha NR, Bhattacherjee D, Das P (2014) Tetrahedron Lett 55:2912
Hu J, Ding Y, Zhang H, Wu P, Li X (2016) RSC Adv 6:3235
Feng J, Handa S, Gallou F, Lipshutz BH (2016) Angew Chem Int Edit 55:8979
Ganji S, Enumula SS, Marella RK, Rao KSR, Burri DR (2014) Catal Sci Technol 4:1813
Begum R, Farooqi ZH, Aboo AH, Ahmed E, Sharif A, Xiao J (2019) J Hazard Mater 377:399
Wang GS, Ding ZQ, Meng LX, Yan GY, Chen ZP, Hu JS (2020) Appl Organomet Chem 34:e5907
Ghasemzadeh MA, Abdollahi-Basir MH, Babaei M (2015) Green Che Lett Rev 8:40
Yuan Q, Chi Y, Yu N, Zhao Y, Yan W, Li X, Dong B (2014) Mater Res Bull 49:279
Rafiee F, Mehdizadeh N (2018) Catal Lett 148:1345
Arghan M, Koukabi N, Kolvari E (2018) Appl Organometal Chem. 32:e4346
Ojeda M, Rojas S, Boutonnet M, Perez-Alonso FJ, Garcia-Garcia FJ, Fierro JLG (2004) Appl Catal A-Gen 274:33
Romanazzi G, Fiorea AM, Mali M, Rizzuti A, Leonelli C, Nacci A, Mastrorilli P, Dell’Annaa MM (2021) Mol Cata 499:31
Ramtenki V, Anumon V, Badiger MV, Prasad B (2012) Colloid Surf A Physicochem Eng Asp 414:296
Junejo Y, Karaoglu E, Baykal A (2013) J Inorg Organomet P 23:970
Qin L, Zeng Z, Zeng G, Lai C, Duan A, Xiao A, Huang D, Fu Y, Yi H, Li B (2019) Appl Catal B Environ 259:118035
Umamaheswari C, Lakshmanan A, Nagarajan NS (2018) J Photoch Photobio B B 178:33
Sargin I, Baran T, Arslan G (2020) Sep Purif Technol 247:116987
Shi W, Lv H, Yuan S, Huang H, Liu Y, Kang Z (2017) Sep Purif Technol 174:282
Issaabadi Z, Nasrollahzadeh M, Sajadi SM (2017) J Clean Prod 142:3584
Acknowledgements
This work was supported by the National Natural Science Foundation of China (21702026, 21861040), Fundamental Research Funds for the Central Universities (N2005004, N2105005), and Scientific Research Fund project of Ningde Normal University (2020Z02, 2018Y06, 2018T02).
Author information
Authors and Affiliations
Corresponding authors
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Wang, G., Chen, Z., Chen, T. et al. Rhodium nanoparticles supported on 2-(aminomethyl)phenols-modified Fe3O4 spheres as a magnetically recoverable catalyst for reduction of nitroarenes and the degradation of dyes in water. Catal Lett 152, 1076–1085 (2022). https://doi.org/10.1007/s10562-021-03688-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-021-03688-4