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Journal of Chemical Sciences

, 130:160 | Cite as

Synthesis, characterization, and application of easily accessible resin-encapsulated nickel nanocatalyst for efficient reduction of functionalized nitroarenes under mild conditions

  • Poonam Rani
  • Kamal Nain Singh
  • Amarjit Kaur
Regular Article
  • 38 Downloads

Abstract

A novel resin-encapsulated nickel nanocatalyst has been synthesized by a modified impregnation method using nickel acetate tetrahydrate in presence of sodium borohydride as a mild reducing agent. The synthesized nanocatalyst was characterized by field emission scanning electron microscopy (FESEM) and transmission electron microscopy (TEM). The concentration of nickel nanoparticles encapsulated on resin was determined by inductively coupled plasma-mass spectroscopy (ICP-MS). Further, synthesized resin-encapsulated nickel nanocatalyst was found to be stable and efficient in micromolar concentrations, for the selective reduction of functionalized nitroarenes to corresponding amines in good to high yield, under mild reaction conditions. The nanocatalyst shows excellent reusability.

Graphical Abstract

SYNOPSIS A novel resin-encapsulated nickel nanocatalyst (Ni@XAD-4) was synthesized using a modified impregnation method. The nanocatalyst exhibited excellent catalytic activity towards the selective reduction of functionalized nitroarenes in the presence of \(\hbox {NaBH}_{4}\) with reusability up to five cycles.

Keywords

Resin-encapsulated nickel nanocatalyst impregnation stability recyclability reduction nitroarenes aromatic amines 

Notes

Acknowledgements

The authors acknowledge the financial support from Science and Engineering Research Board (SERB)-DST, New Delhi, through Scheme number EEQ/2016/000574, CRF, IIT Delhi for HR-TEM and TEM-EDS analysis, PBTI, Mohali for ICP-MS characterization and SAIF, Punjab University for \(^{1}\hbox {H NMR}\) and \(^{13}\hbox {C NMR}\) and other characteristic techniques.

Supplementary material

12039_2018_1548_MOESM1_ESM.pdf (1.3 mb)
Supplementary material 1 (pdf 1320 KB)

References

  1. 1.
    Talmage S S, Opresko D M, Maxwell C J, Welsh C J, Cretella F M, Reno P H and Daniel F B 1999 Nitroaromatic munition compounds: environmental effects and screening values Rev. Environ. Contam. Toxicol. 1611Google Scholar
  2. 2.
    Kovacic P and Somanathan R 2014 Nitroaromatic compounds: Environmental toxicity, carcinogenicity, mutagenicity, therapy and mechanism J. Appl. Toxicol. 34 810CrossRefGoogle Scholar
  3. 3.
    Yan F, He Y, Ding L and Su B 2015 Highly ordered binary assembly of silica mesochannels and surfactant micelles for extraction and electrochemical analysis of trace nitroaromatic explosives and pesticides Anal. Chem. 87 4436CrossRefGoogle Scholar
  4. 4.
    Liu X, Ma X, Liu S, Liu Y and Xia C 2015 Metal fluoride promoted catalytic hydrogenation of aromatic nitro compounds over RANEY® Ni RSC Adv. 5 36423CrossRefGoogle Scholar
  5. 5.
    Deiber G, Foussard J N and Debellefontaine H 1997 Removal of nitrogenous compounds by catalytic wet air oxidation. Kinetic study Environ. Pollut. 96 311CrossRefGoogle Scholar
  6. 6.
    Keiichi T, Wandee L and Teruaki H 1997 Photocatalytic degradation of mono-, di- and trinitrophenol in aqueous \(\text{ TiO }_{2}\) suspension. J. Mol. Catal. A: Chem. 122 67CrossRefGoogle Scholar
  7. 7.
    Clemenceau A, Wang Q and Zhu J 2018 Cooperative Pd/Cu catalysis: multicomponent synthesis of tetrasubstituted imidazolones from methyl \(\upalpha \)Isocyanoacetates, primary amines, and aryl(vinyl) iodides Org. Lett. 20 126CrossRefGoogle Scholar
  8. 8.
    Mei N, Liu B and Bing V Int. 2016 Pd nanoparticles supported on Fe3O4@C: An effective heterogeneous catalyst for the transfer hydrogenation of nitro compounds into amines J. Hydrog. Energy 41 17960CrossRefGoogle Scholar
  9. 9.
    Morse J R, Callejas J F, Darling A J and Schaak R E 2017 Bulk iron pyrite as a catalyst for the selective hydrogenation of nitroarenes Chem. Commun. 53 4807CrossRefGoogle Scholar
  10. 10.
    Kalyanaraman V and George M V 1973 Alkali metal reduction of aromatic nitro compounds J. Org. Chem. 38 507CrossRefGoogle Scholar
  11. 11.
    Asghar A S and Kazemi F 2016 Photocatalytic reduction of nitroaromatic compounds to amines using a nanosized highly active CdS photocatalyst under sunlight and blue LED irradiation Chem. Pap. 70 531Google Scholar
  12. 12.
    Qi Z, Dong H, Yu H, Zhao M and Yu H 2017 In-situ electrochemical NOx removal process for the lean-burn engine exhaust based on carbon black gas diffusion electrode J. Clean. Prod. 151 465CrossRefGoogle Scholar
  13. 13.
    Li Y, Gong Y, Xu X, Zhang P, Li H and Wang Y 2012 A practical and benign synthesis of amines through \(\text{ Pd@mpg-C }_{3}\text{ N }_{4}\) catalyzed reduction of nitriles Catal. Commun. 28 9CrossRefGoogle Scholar
  14. 14.
    Blanita G and Lazar M D 2013 Review of graphene-supported metal nanoparticles as new and efficient heterogeneous catalysts Micro Nanosyst. 5 138CrossRefGoogle Scholar
  15. 15.
    Segobia D, Trasarti A and Apesteguia C 2012 Hydrogenation of nitriles to primary amines on metal-supported catalysts: Highly selective conversion of butyronitrile to n-butylamine Appl. Catal. A 445 69CrossRefGoogle Scholar
  16. 16.
    Tumma M and Srivastava R 2013 Transition metal nanoparticles supported on mesoporous polyaniline catalyzed the reduction of nitroaromatics Catal. Commun. 37 64CrossRefGoogle Scholar
  17. 17.
    Jamal S, Rezaei T, Khorramabadi H, Hesami A, Ramazani A, Amani V and Ahmadi R 2017 Chemoselective reduction of nitro and nitrile compounds with magnetic carbon nanotubes supported Pt(II) catalyst under mild conditions Ind. Eng. Chem. Res. 56 12256CrossRefGoogle Scholar
  18. 18.
    Zuoa P, Duana J, Fana H, Qua S and Shen W 2018 Facile synthesis high nitrogen-doped porous carbon nanosheet from pomelo peel and as catalyst support for nitrobenzene hydrogenation Appl. Surf. Sci. 435 1020CrossRefGoogle Scholar
  19. 19.
    Cao Y, He L and Ni J 2011 Method for the synthesis of amine by reduction of nitro compound in presence of a metal oxide-supported gold catalyst Faming Zhuanli Shenqing CN 102086143 A 20110608Google Scholar
  20. 20.
    Mohammadi-Aghdam B, Bahari S and Molaei R 2013 The Pd (0) nanoparticles stabilized by collagen fibres as a recyclable heterogeneous catalyst for the Stille reaction under aerobic condition J. Chem. Sci. 125 813CrossRefGoogle Scholar
  21. 21.
    Hemantha H P and Sureshbabu V V 2011 Poly(vinyl)chloride supported palladium nanoparticles: a catalyst for rapid hydrogenation reactions Org. Biomol. Chem. 9 2597CrossRefGoogle Scholar
  22. 22.
    Lara P and Philippot K 2014 The hydrogenation of nitroarenes mediated by platinum nanoparticles: an overview Catal. Sci. Technol. 4 2445CrossRefGoogle Scholar
  23. 23.
    Chaiseeda K, Nishimura S and Ebitani K 2017 Gold nanoparticles supported on alumina as a catalyst for surface plasmon-enhanced selective reductions of nitrobenzene ACS Omega 2 7066CrossRefGoogle Scholar
  24. 24.
    Feng W, Huang T, Gao L, Yang X, Deng W, Zhou R and Liu H 2018 Textile-supported silver nanoparticles as a highly efficient and recyclable heterogeneous catalyst for nitroaromatic reduction at room temperature RSC Adv. 8 6288CrossRefGoogle Scholar
  25. 25.
    Viswanathan P and Ramaraj R 2018 Gold nanodots self-assembled polyelectrolyte film as reusable catalyst for reduction of nitroaromatics J. Chem. Sci. 130 10CrossRefGoogle Scholar
  26. 26.
    Shang H, Pan K, Zhang L, Zhang B and Xiang X 2016 Enhanced activity of supported Ni catalysts promoted by Pt for rapid reduction of aromatic nitro compounds Nanometre 6 103CrossRefGoogle Scholar
  27. 27.
    Ai Y, Liua L, Jing K, Qi L, Fana Z, Zhoua J, Suna H-Bin, Shao Z and Liang Q 2017 Noncovalently functionalized carbon nanotubes immobilized Fe-Bi bimetallic oxides as a heterogeneous nanocatalyst for reduction of nitroaromatics NANOSO 10 116Google Scholar
  28. 28.
    Barot N, Shaikh T and Kaur H 2017 A \(\text{ PLA-TiO }_{2}\) particle brush as a novel support for CuNPs: a catalyst for the fast-sequential reduction and N-arylation of nitroarenes New J. Chem. 41 5347CrossRefGoogle Scholar
  29. 29.
    Sorribes I, Liu L and Corma A 2017 Nanolayered Co-Mo-S catalysts for the chemoselective hydrogenation of nitroarenes ACS Catal. 7 2698CrossRefGoogle Scholar
  30. 30.
    Ayoub H, Lair V, Griveau S, Brunswick P, Bedioui F and Cassir M 2011 SUDOSCAN device for the early detection of diabetes: in vitro measurement versus results of clinical tests Sensor Lett. 9 2147CrossRefGoogle Scholar
  31. 31.
    Yu J and Xu G 2018 A kind of cobalt nickel super capacitor electrode and its preparation process [Machine Translation] Faming Zhuanli Shenqing CN 107658150 A 20180202Google Scholar
  32. 32.
    Jamal S, Rezaei T, Malekzadeh A M, Poulaei S, Ramazani A and Khorramabadi H 2018 Chemo-selective reduction of nitro and nitrile compounds using Ni nanoparticles immobilized on hyperbranched polymer-functionalized magnetic nanoparticles Appl. Organometal. Chem. 32 3975CrossRefGoogle Scholar
  33. 33.
    Meng X, Cheng H, Akiyama Y, Hao Y, Qiao W, Yu Y, Zhao F, Fujita S and Arai M 2009 Selective hydrogenation of nitrobenzene to aniline in dense phase carbon dioxide over \(\text{ Ni }/\text{ C-Al }_{2}\text{ O }_{3}\): significance of molecular interactions J. Catal. 264 1CrossRefGoogle Scholar
  34. 34.
    Romanazzi G, Fiore A M, Malia M, Rizzuti A, Leonelli C, Nacci A, Mastrorilli P and Dell’Annaa M M 2018. Polymer supported Nickel nanoparticles as recyclable catalyst for the reduction of nitroarenes to anilines in aqueous medium Mol. Catal. 446 31CrossRefGoogle Scholar
  35. 35.
    Yadagiri J, Koppadi K S, Enumula S S, Vakati V, Kamaraju S R R, Burri D R and Somaiah P V 2018 Ni/KIT-6 catalysts for hydrogenolysis of lignin-derived diphenyl ether J. Chem. Sci. 130 106CrossRefGoogle Scholar
  36. 36.
    Kalbasi R J, Nourbakhsh A A and Babaknezhad F 2011 Synthesis and characterization of Ni nanoparticles-polyvinylamine/SBA-15 catalyst for simple reduction of aromatic nitro compounds Catal. Commun. 12 955CrossRefGoogle Scholar
  37. 37.
    Mahata N, Cunha A F, Orfao J J M and Figueiredo J L 2008 Hydrogenation of nitrobenzene over nickel nanoparticles stabilized by filamentous carbon Appl. Catal. A: Gen. 351 204CrossRefGoogle Scholar
  38. 38.
    Dey R, Mukherjee N, Ahammed S and Ranu B C 2012 Highly selective reduction of nitroarenes by iron(0) nanoparticles in water Chem. Commun. 48 7982CrossRefGoogle Scholar
  39. 39.
    Shah D and Kaur H 2014 Resin-trapped gold nanoparticles: An efficient catalyst for reduction of nitro compounds and Suzuki-Miyaura coupling J. Mol. Catal. A: Chem. 381 70CrossRefGoogle Scholar
  40. 40.
    Bordbar M 2017 Biosynthesis of Ag/almond shell nanocomposite as a cost-effiective and efficient catalyst for degradation of 4-nitrophenol and organic dyes RSC Adv. 7 180CrossRefGoogle Scholar
  41. 41.
    Zhao Y, Luo Y, Yang X, Yang Y and Song Q 2017 Tunable preparation of ruthenium nanoparticles with superior size-dependent catalytic hydrogenation properties J. Hazard. Mater. 332 124CrossRefGoogle Scholar
  42. 42.
    Kang H, Kim M and Park K H 2015 Effective immobilization of gold nanoparticles on core-shell thiol-functionalized GO coated \(\text{ TiO }_{2}\) and their catalytic application in the reduction of \(4\)-nitrophenol Appl. Catal. A: Gen. 502 239CrossRefGoogle Scholar
  43. 43.
    Wang A, Yin H, Lu H, Xue J, Ren M and Jiang T 2009 Effect of organic modifiers on the structure of nickel nanoparticles and catalytic activity in the hydrogenation of \(p\)-nitrophenol to \(p\)-aminophenol Langmuir 25 12736CrossRefGoogle Scholar
  44. 44.
    Sahiner N, Yildiz S and Al-Lohedan H 2015 The resourcefulness of \(p\)(4-VP) cryogels as template for in situ nanoparticle preparation of various metals and their use in \(\text{ H }_{2}\) production, nitro compound reduction and dye degradation Appl. Catal. B: Environ. 166 145CrossRefGoogle Scholar
  45. 45.
    Liu K, Wang Y, Cheng P, Liu Y, Kong C, Yi Z, Li M, Liu Q, Zhong W, Takagi H and Wang D 2018 Nanosized nickel decorated sisal fibers with tailored aggregation structures for catalysis reduction of toxic aromatic compounds Ind. Crops Prod. 119 226CrossRefGoogle Scholar
  46. 46.
    Kang J, Han R, Wang J, Yang L, Fan G and Li F 2015 In situ synthesis of nickel carbide-promoted nickel/carbon nanofibers nanocomposite catalysts for catalytic applications Chem. Eng. J. 275 36CrossRefGoogle Scholar

Copyright information

© Indian Academy of Sciences 2018

Authors and Affiliations

  1. 1.Department of Chemistry, Faculty of SciencePanjab UniversityChandigarhIndia

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