Abstract
Heterogeneous catalysts based on metallic nanoparticles are promising candidates for wastewater treatment. However, they aggregate easily as a result of their high surface energy. Polymers are very popular supporting catalyst materials because they can stabilize the metallic nanoparticles to prevent aggregation. In this study, aniline-pentamer-based electroactive polyurea (EPU) was synthesized by oxidative coupling, and Au nanoparticles were anchored to the EPU via its aniline segments. Electrochemical redox behavior of the as-synthesized EPU was monitored by electrochemical cyclic voltammetry. The Au/EPU composite was characterized by FTIR, UV–vis, TGA, SEM, TEM, XRD XPS, and ICP-OES. SEM showed that the EPU had a flower-like structure, and the Au nanoparticles were uniformly immobilized on the EPU surface. The reduction of 4-nitrophenol (4-NP) by NaBH4 was used as a model reaction to evaluate the catalytic properties of the Au/EPU composite. Moreover, the optimization of the reaction conditions for the reduction of 4-NP to 4-aminophenol (4-AP) were also studied in detail. The Au/EPU composite catalyzed the reduction of 4-NP to 4-AP within 4 min with a rate constant of 2.4 × 10–2 s−1 and an activation energy of 40.17 kJ/mol. The Au/EPU composite demonstrated high conversion (98%) after 20 successive cycles.
Graphical abstract
Similar content being viewed by others
References
Yılmaz Baran N (2020) J Mol Struct 1220:128697
Serrà A, Artal R, Pozo M, Garcia-Amorós J, Gómez E (2020) Catalysts 10:458
Verma A, Kumar S, Chang W-K, Fu Y-P (2020) Dalton Trans 49:625–637
Naghdi S, Sajjadi M, Nasrollahzadeh M, Rhee KY, Sajadi SM, Jaleh B (2018) J Taiwan Inst Chem Eng 86:158–173
Nasrollahzadeh M, Issaabadi Z, Sajadi SM (2018) Sep Purif Technol 197:253–260
Li S, Li H, Liu J, Zhang H, Yang Y, Yang Z, Wang L, Wang B (2015) Dalton Trans 44:9193–9199
Zhang Z, Sun T, Chen C, Xiao F, Gong Z, Wang S (2014) ACS Appl Mater Interfaces 6:21035–21040
Nasrollahzadeh M, Nezafat Z, Gorab MG, Sajjadi M (2020) Mol Catal 484:110758
Yao H, Huang T-C, Sue H-J (2014) RSC Adv 4:61823–61830
Nasrollahzadeh M, Sajjadi M, Iravani S, Varma RS (2021) Chemosphere 263:128005
Lai G-H, Huang T-C, Pai Y-H, Huang B-S, Tsai M-H, Yang T-I, Chung Y-H (2019) J Taiwan Inst Chem Eng 95:525–531
Yek SM-G, Baran T, Nasrollahzadeh M, Bakhshali-Dehkordi R, Baran NY, Shokouhimehr M (2021) Optik 238:166672
Nasrollahzadeh M, Sajjadi M, Iravani S, Varma RS (2021) Carbohydr Polym 251:116986
Koga H, Tokunaga E, Hidaka M, Umemura Y, Saito T, Isogai A, Kitaoka T (2010) Chem Commun 46:8567–8569
Mohazzab BF, Jaleh B, Nasrollahzadeh M, Issaabadi Z, Varma RS (2019) Mol Catal 473:110401
Gawande MB, Rathi AK, Tucek J, Safarova K, Bundaleski N, Teodoro OMND, Kvitek L, Varma RS, Zboril R (2014) Green Chem 16:4137–4143
Orooji Y, Akbari R, Nezafat Z, Nasrollahzadeh M, Kamali TA (2021) J Mol Liq 329:115583
Lai G-H, Huang B-S, Yang T-I, Tsai M-H, Chou Y-C (2021) Polymer 213:123200
Zhu C, Han L, Hu P, Dong S (2012) Nanoscale 4:1641–1646
Tajbakhsh M, Alinezhad H, Nasrollahzadeh M, Kamali TA (2016) J Alloys Compd 685:258–265
Nasrollahzadeh M, Sajjadi M, Iravani S, Varma RS (2021) J Hazard Mater 401:123401
Baran T, Nasrollahzadeh M (2019) Carbohydr Polym 222:115029
Nezafat Z, Nasrollahzadeh M (2021) J Mol Struct 1228:129731
Zheng H, Huang J, Zhou T, Jiang Y, Jiang Y, Gao M, Liu Y (2020) Catalysts 10:1437
Lai G-H, Chou Y-C, Huang B-S, Yang T-I, Tsai M-H (2021) RSC Adv 11:71–77
Zhou J, Zhang C, Wang Y (2019) Polym Chem 10:1642–1649
Hao B, Lu G, Zhang S, Li Y, Ding A, Huang X (2020) Polym Chem 11:4094–4104
Tsai MH, Lu SH, Lai YH, Lai GH, Dizon GV, Yang TI, Lin YJ, Chou YC (2018) Express Polym Lett 12:71–81
Ji W-F, Chu C-M, Hsu S-C, Lu Y-D, Yu Y-C, Santiago KS, Yeh J-M (2017) Polymer 128:218–228
Palza H, Zapata PA, Angulo-Pineda C (2019) Materials 12:277
Huang T-C, Yeh L-C, Lai G-H, Huang B-S, Yang T-I, Hsu S-C, Lo A-Y, Yeh J-M (2017) Int J Green Energy 14:113–120
Huang TC, Yeh JM, Lai CY (2012) In: Gao F (ed) Advances in polymer nanocomposites. Woodhead Publishing.
Huang T-C, Lin S-T, Yeh L-C, Chen C-A, Huang H-Y, Nian Z-Y, Chen H-H, Yeh J-M (2012) Polymer 53:4373–4379
Huang T-C, Yeh L-C, Huang H-Y, Nian Z-Y, Yeh Y-C, Chou Y-C, Yeh J-M, Tsai M-H (2014) Polym Chem 5:630–637
Huang H-Y, Lee Y-T, Yeh L-C, Jian J-W, Huang T-C, Liang H-T, Yeh J-M, Chou Y-C (2013) Polym Chem 4:343–350
Huang H-Y, Jian J-W, Lee Y-T, Li Y-T, Huang T-C, Chang J-H, Yeh L-C, Yeh J-M (2012) Polymer 53:4967–4976
Xu F, Guo S, Luo Y-L (2014) Mater Chem Phys 145:222–231
Huang T-C, Lai G-H, Li C-E, Tsai M-H, Wan P-Y, Chung Y-H, Lin M-H (2017) RSC Adv 7:9908–9913
Yeh L-C, Huang T-C, Lai F-Y, Lai G-H, Lo A-Y, Hsu S-C, Yang T-I, Yeh J-M (2016) Surf Coat Technol 303:154–161
Yeh L-C, Huang T-C, Huang Y-P, Huang H-Y, Chen H-H, Yang T-I, Yeh J-M (2013) Electrochim Acta 94:300–306
Huang T-C, Yeh T-C, Huang H-Y, Ji W-F, Lin T-C, Chen C-A, Yang T-I, Yeh J-M (2012) Electrochim Acta 63:185–191
Bastús NG, Comenge J, Puntes V (2011) Langmuir 27:11098–11105
Shao Z, Yu Z, Hu J, Chandrasekaran S, Lindsay DM, Wei Z, Faul CFJ (2012) J Mater Chem 22:16230–16234
Chao D, Ma X, Liu Q, Lu X, Chen J, Wang L, Zhang W, Wei Y (2006) Eur Polym J 42:3078–3084
Yi L, Meng Y, Yang S, Fei J, Ding Y, Wang X, Lu Y (2020) New J Chem 44:6940–6946
Yeh J-M, Huang K-Y, Lin S-Y, Wu Y-Y, Huang C-C, Liou S-J (2009) J Nanotechnol 2009:217469
Liu J, Wu Z, He Q, Tian Q, Wu W, Xiao X, Jiang C (2019) Nanoscale Res Lett 14:35
Kar P, Sardar S, Liu B, Sreemany M, Lemmens P, Ghosh S, Pal SK (2016) Sci Technol Adv Mater 17:375–386
Liu X, Cui X, Liu Y, Yin Y (2015) Nanoscale 7:18320–18326
Liu M, Cui F, Ma Q, Xu L, Zhang J, Zhang R, Cui T (2020) New J Chem 44:4042–4048
Wunder S, Polzer F, Lu Y, Mei Y, Ballauff M (2010) J Phys Chem C 114:8814–8820
Tang J, Shi Z, Berry RM, Tam KC (2015) Ind Eng Chem Res 54:3299–3308
Qin L, Zeng Z, Zeng G, Lai C, Duan A, Xiao R, Huang D, Fu Y, Yi H, Li B, Liu X, Liu S, Zhang M, Jiang D (2019) Appl Catal B 259:118035
Pradhan N, Pal A, Pal T (2002) Colloids Surf A 196:247–257
Sun L, Peng S, Jiang L, Zheng Y, Sun X, Su H, Qi C (2019) Colloid Polym Sci 297:651–659
Deshmukh SP, Dhodamani AG, Patil SM, Mullani SB, More KV, Delekar SD (2020) ACS Omega 5:219–227
Kuroda K, Ishida T, Haruta M (2009) J Mol Catal A Chem 298:7–11
Guo R, Jiao T, Xing R, Chen Y, Guo W, Zhou J, Zhang L, Peng Q (2017) Nanomaterials 7:317
Lai G-H, Huang T-C, Huang B-S, Chou Y-C (2021) RSC Adv 11:33990–33995
Acknowledgements
We would like to thank the Ministry of Science and Technology, Taiwan, under Grant Number MOST 109-2637-E-241-004, MOST 110-2637-E-241-003, for their financial support. Special thanks are given to the National Chung Hsing University (MOST 108-2731-M-005-001-) for the LC-Mass, SEM, TEM, XPS support.
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
Lai, GH., Huang, BS., Yang, TI. et al. Highly Efficient and Recyclable Au/Aniline-Pentamer-Based Electroactive Polyurea Catalyst for the Reduction of 4-Nitrophenol. Catal Lett 152, 3100–3109 (2022). https://doi.org/10.1007/s10562-021-03876-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-021-03876-2