journal article·2019-05

Ni nanoparticles on polyaromatic hyperbranched polymer support as a mild, tunable, and sustainable catalyst for catalytic transfer hydrogenation

S. Basaveni, N. V. Kuchkina, Z. B. Shifrina, M. Pal, M. Rajadurai

Journal of Nanoparticle Research· Volume 21· Issue 5
Publisher page

Abstract

Hyperbranched polyaromatic polymer (HBP) based on pyridylphenylene dendrimer as a multifunctional monomer was employed as a nanoreactor and a stabilizing matrix for synthesis of catalytic Ni nanoparticles (NPs). The HBP was found to have an effective control over NP size. The Ni NPs synthesized in HBP matrix had diameter between 3 and 4.5 nm with narrow size distribution and were reproducible in several batches. The HBP-encapsulated Ni NPs (Ni-HBP) had a good air stability, high activity, and controlled reactivity in catalytic transfer hydrogenation (CTH) of nitroarenes and alkenes. The catalytic reactions were performed under base-free, heterogeneously-catalyzed conditions without use of high pressure, strong acidic media, or highly flammable hydrogen source. This reduction system showed good tolerance towards hydroxyl, alkyne, or halogen substituents. Moreover, due to mild nature of the catalyst, the reaction may be controlled to selectively reduce only one functional group, leaving another one intact (e.g., nitro-group vs internal alkyne).
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Asymmetric Hydrogenation and Catalysis · Nanomaterials for catalytic reactions · Catalysis and Hydrodesulfurization Studies

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (46)

Show source-provided references
1. Abd El Maksod IH, Saleh TS (2010) The use of nano supported nickel catalyst in reduction of p -nitrophenol using hydrazine as hydrogen donor. Green Chem Lett Rev 3:127–134. https://doi.org/10.1080/1751825100359614310.1080/17518251003596143 ↗
2. Alonso F, Riente P, Sirvent JA, Yus M (2010) Nickel nanoparticles in hydrogen-transfer reductions: characterisation and nature of the catalyst. Appl Catal A Gen 378:42–51. https://doi.org/10.1016/J.APCATA.2010.01.04410.1016/J.APCATA.2010.01.044 ↗
3. Alonso F, Riente P, Yus M (2011) Nickel nanoparticles in hydrogen transfer reactions. Acc Chem Res 44:379–391. https://doi.org/10.1021/ar100158210.1021/ar1001582 ↗
4. Ananikov VP (2015) Nickel: the “spirited horse” of transition metal catalysis. ACS Catal 5:1964–1971. https://doi.org/10.1021/acscatal.5b0007210.1021/acscatal.5b00072 ↗
5. Astruc D (Didier), Wiley InterScience (Online service) (2008) Nanoparticles and catalysis. Wiley-VCH, Weinheim
6. Baird N, Dittmar JW, Losovyj YB, Morgan DG, Stein BD, Pink M, Kuchkina NV, Serkova ES, Lependina OL, Grigoriev ME, Sidorov AI, Sulman MG, Shifrina ZB, Bronstein LM (2017) Enhancing the catalytic activity of Zn-containing magnetic oxides in a methanol synthesis: identifying the key factors. ACS Appl Mater Interfaces 9:2285–2294. https://doi.org/10.1021/acsami.6b1211510.1021/acsami.6b12115 ↗
7. Bayazit MK, Yue J, Cao E, Gavriilidis A, Tang J (2016) Controllable synthesis of gold nanoparticles in aqueous solution by microwave assisted flow chemistry. ACS Sustain Chem Eng 4:6435–6442. https://doi.org/10.1021/acssuschemeng.6b0114910.1021/acssuschemeng.6b01149 ↗
8. Bullock RM (2013) Abundant metals give precious hydrogenation performance. Science 342:1054–1055. https://doi.org/10.1126/science.124724010.1126/science.1247240 ↗
9. Hareesh HN, Minchitha KU, Venkatesh K, Nagaraju N, Kathyayini N (2016) Environmentally benign selective hydrogenation of α,β-unsaturated aldehydes and reduction of aromatic nitro compounds using Cu based bimetallic nanoparticles supported on multiwalled carbon nanotubes and mesoporous carbon. RSC Adv 6:82359–82369. https://doi.org/10.1039/C6RA04241D10.1039/C6RA04241D ↗
10. Holzwarth MS, Plietker B (2013) Biorelevant metals in sustainable metal catalysis-a survey. ChemCatChem 5:1650–1679. https://doi.org/10.1002/cctc.20120059210.1002/cctc.201200592 ↗
11. Hu H, Xin JH, Hu H, Wang X, Miao D, Liu Y (2015) Synthesis and stabilization of metal nanocatalysts for reduction reactions – a review. J Mater Chem A 3:11157–11182. https://doi.org/10.1039/C5TA00753D10.1039/C5TA00753D ↗
12. Kadam HK, Tilve SG (2015) Advancement in methodologies for reduction of nitroarenes. RSC Adv 5:83391–83407. https://doi.org/10.1039/C5RA10076C10.1039/C5RA10076C ↗
13. Kalbasi RJ, Zamani F (2014) Synthesis and characterization of Ni nanoparticles incorporated into hyperbranched polyamidoamine–polyvinylamine/SBA-15 catalyst for simple reduction of nitro aromatic compounds. RSC Adv 4:7444. https://doi.org/10.1039/c3ra44662j10.1039/c3ra44662j ↗
14. Koga T, Nabae Y, Funakawa A, Hayakawa T, Kakimoto M (2017) Synthesis of hyperbranched polypyridine via a cross coupling approach as an n-type π-conjugated polymer. Macromol Chem Phys 218:1700391. https://doi.org/10.1002/macp.20170039110.1002/macp.201700391 ↗
15. Kotel’nikova NE, Lysenko EL, Serimaa R, Pirkkalainen K, Vainio U, Lavrent’ev VK, Medvedeva DA, Shakhmin AL, Saprykina NN, Novoselov NP (2008) Cellulose as a nanoreactor for the synthesis of nickel nanoparticles. Polym Sci Ser A 50:51–57. https://doi.org/10.1134/S0965545X0801009410.1134/S0965545X08010094 ↗
16. Kuchkina NV, Yuzik-Klimova EY, Sorokina SA, Peregudov AS, Antonov DY, Gage SH, Boris BS, Nikoshvili LZ, Sulman EM, Morgan DG, Mahmoud WE, Al-Ghamdi AA, Bronstein LM, Shifrina ZB (2013) Polyphenylenepyridyl dendrons with functional periphery and focal points: syntheses and applications. Macromolecules 46:5890–5898. https://doi.org/10.1021/ma401043u10.1021/ma401043u ↗
17. Kuchkina NV, Morgan DG, Kostopoulou A, Lappas A, Brintakis K, Boris BS, Yuzik-Klimova EY, Stein BD, Svergun DI, Spilotros A, Sulman MG, Nikoshvili LZ, Sulman EM, Shifrina ZB, Bronstein LM (2014) Hydrophobic periphery tails of polyphenylenepyridyl dendrons control nanoparticle formation and catalytic properties. Chem Mater 26:5654–5663. https://doi.org/10.1021/cm502336n10.1021/cm502336n ↗
18. Kuchkina NV, Zinatullina MS, Serkova ES, Vlasov PS, Peregudov AS, Shifrina ZB (2015) Hyperbranched pyridylphenylene polymers based on the first-generation dendrimer as a multifunctional monomer. RSC Adv 5:99510–99516. https://doi.org/10.1039/C5RA16847C10.1039/C5RA16847C ↗
19. Kuchkina NV, Rajadurai M, Pal M, Basaveni S, Sorokina SA, Krasnova IY, Serkova ES, Shifrina ZB (2018) Catalysts based on hyperbranched pyridylphenylene polymers and palladium nanoparticles for the Suzuki—Miyaura cross-coupling reaction. Russ Chem Bull 67:1035–1040. https://doi.org/10.1007/s11172-018-2176-610.1007/s11172-018-2176-6 ↗
20. Leadbeater NE (2001) Bis-cyclopentadienyl nickel (nickelocene): a convenient starting material for reactions catalyzed by Ni(O) phosphine complexes. J Organomet Chem 66:7539–7541. https://doi.org/10.1021/jo015837710.1021/jo0158377 ↗
21. Lim J-M, Swami A, Gilson LM, Chopra S, Choi S, Wu J, Langer R, Karnik R, Farokhzad OC (2014) Ultra-high throughput synthesis of nanoparticles with homogeneous size distribution using a coaxial turbulent jet mixer. ACS Nano 8:6056–6065. https://doi.org/10.1021/nn501371n10.1021/nn501371n ↗
22. Lin W, Cheng H, Ming J, Yu Y, Zhao F (2012) Deactivation of Ni/TiO2 catalyst in the hydrogenation of nitrobenzene in water and improvement in its stability by coating a layer of hydrophobic carbon. J Catal 291:149–154. https://doi.org/10.1016/J.JCAT.2012.04.02010.1016/J.JCAT.2012.04.020 ↗
23. Marakatti VS, Peter SC (2016) Nickel–antimony nanoparticles confined in SBA-15 as highly efficient catalysts for the hydrogenation of nitroarenes. New J Chem 40:5448–5457. https://doi.org/10.1039/C5NJ03479E10.1039/C5NJ03479E ↗
24. Marguí E, Fontàs C, Buendía A, Hidalgo M, Queralt I (2009) Determination of metal residues in active pharmaceutical ingredients according to European current legislation by using X-ray fluorescence spectrometry. J Anal At Spectrom 24:1253–1257. https://doi.org/10.1039/b904064a10.1039/b904064a ↗
25. Mizugaki T, Kibata T, Ota K, Mitsudome T, Ebitani K, Jitsukawa K, Kaneda K (2009) Controlled synthesis of Pd clusters in subnanometer range using poly(propylene imine) dendrimers. Chem Lett 38:1118–1119. https://doi.org/10.1246/cl.2009.111810.1246/cl.2009.1118 ↗
26. Navalón S, García H (2016) Nanoparticles for catalysis. Nanomaterials. 6. https://doi.org/10.3390/NANO607012310.3390/nano6070123 ↗
27. Niu Y, Crooks RM (2003) Dendrimer-encapsulated metal nanoparticles and their applications to catalysis. C R Chimie 6:1049–1059. https://doi.org/10.1016/J.CRCI.2003.08.00110.1016/J.CRCI.2003.08.001 ↗
28. Özhava D, Kılıçaslan NZ, Özkar S (2015) PVP-stabilized nickel(0) nanoparticles as catalyst in hydrogen generation from the methanolysis of hydrazine borane or ammonia borane. Appl Catal B Environ 162:573–582. https://doi.org/10.1016/j.apcatb.2014.07.03310.1016/j.apcatb.2014.07.033 ↗
29. Rai RK, Mahata A, Mukhopadhyay S, Gupta S, Li P-Z, Nguyen KT, Zhao Y, Pathak B, Singh SK (2014) Room-temperature chemoselective reduction of nitro groups using non-noble metal nanocatalysts in water. Inorg Chem 53:2904–2909. https://doi.org/10.1021/ic402674z10.1021/ic402674z ↗
30. Rehm TH, Bogdan A, Hofmann C, Löb P, Shifrina ZB, Morgan DG, Bronstein LM (2015) Proof of concept: magnetic fixation of dendron-functionalized Iron oxide nanoparticles containing palladium nanoparticles for continuous-flow Suzuki coupling reactions. ACS Appl Mater Interfaces 7:27254–27261. https://doi.org/10.1021/acsami.5b0846610.1021/acsami.5b08466 ↗
31. Romanazzi G, Fiore AM, Mali M, Rizzuti A, Leonelli C, Nacci A, Mastrorilli P, Dell’Anna MM (2018) Polymer supported nickel nanoparticles as recyclable catalyst for the reduction of nitroarenes to anilines in aqueous medium. Mol Catal 446:31–38. https://doi.org/10.1016/J.MCAT.2017.12.01510.1016/J.MCAT.2017.12.015 ↗
32. Roucoux A, Jürgen Schulz A, Patin H (2002) Reduced transition metal colloids: a novel family of reusable catalysts? Chem Rev 102:3757–3778. https://doi.org/10.1021/CR010350J10.1021/CR010350J ↗
33. Shi Y, Liu L, Zhang F, Niu M, Zhao Y, Fan Y, Liang Y, Liu M, Zhang Z, Wang J, Shi Y, Liu L, Zhang F, Niu M, Zhao Y, Fan Y, Liang Y, Liu M, Zhang Z, Wang J (2017) Catalyst system for hydrogenation catalysis based on multiarm hyperbranched polymer templated metal (Au, Pt, Pd, Cu) nanoparticles. Polymers (Basel) 9:459. https://doi.org/10.3390/polym909045910.3390/polym9090459 ↗
34. Shifrina ZB, Rajadurai MS, Firsova NV, Bronstein LM, Huang X, Rusanov AL, Muellen K (2005) Poly(phenylene-pyridyl) dendrimers: synthesis and templating of metal nanoparticles. Macromolecules. 38:9920–9932. https://doi.org/10.1021/ma051802n10.1021/ma051802n ↗
35. Standley EA, Smith SJ, Müller P, Jamison TF (2014) A broadly applicable strategy for entry into homogeneous nickel(0) catalysts from air-stable nickel(II) complexes. Organometallics 33:2012–2018. https://doi.org/10.1021/om500156q10.1021/om500156q ↗
36. Tabatabaei Rezaei SJ, Mashhadi Malekzadeh A, Poulaei S, Ramazani A, Khorramabadi H (2018) Chemo-selective reduction of nitro and nitrile compounds using Ni nanoparticles immobilized on hyperbranched polymer-functionalized magnetic nanoparticles. Appl Organomet Chem 32:e3975. https://doi.org/10.1002/aoc.397510.1002/aoc.3975 ↗
37. Takahashi M, Koizumi H, Chun W-J, Kori M, Imaoka T, Yamamoto K (2017) Finely controlled multimetallic nanocluster catalysts for solvent-free aerobic oxidation of hydrocarbons. Sci Adv 3:e1700101. https://doi.org/10.1126/sciadv.170010110.1126/sciadv.1700101 ↗
38. Tuteja J, Nishimura S, Ebitani K (2014) Base-free chemoselective transfer hydrogenation of nitroarenes to anilines with formic acid as hydrogen source by a reusable heterogeneous Pd/ZrP catalyst. RSC Adv 4:38241–38249. https://doi.org/10.1039/c4ra06174h10.1039/c4ra06174h ↗
39. Vonk V, Khorshidi N, Stierle A (2017) Structure and oxidation behavior of nickel nanoparticles supported by YSZ(111). J Phys Chem C 121:2798–2806. https://doi.org/10.1021/acs.jpcc.6b1134210.1021/acs.jpcc.6b11342 ↗
40. Wang D, Astruc D (2015) The golden age of transfer hydrogenation. Chem Rev 115:6621–6686. https://doi.org/10.1021/acs.chemrev.5b0020310.1021/acs.chemrev.5b00203 ↗
41. Wang D, Astruc D (2017) The recent development of efficient earth-abundant transition-metal nanocatalysts. Chem Soc Rev 46:816–854. https://doi.org/10.1039/C6CS00629A10.1039/C6CS00629A ↗
42. Wang A, Yin H, Ren M, Lu H, Xue J, Jiang T (2010) Preparation of nickel nanoparticles with different sizes and structures and catalytic activity in the hydrogenation of p-nitrophenol. New J Chem 34:708. https://doi.org/10.1039/b9nj00657e10.1039/b9nj00657e ↗
43. Wang C, Sun N, Zhao N, Wei W, Sun Y, Sun C, Liu H, Snape CE (2015) Coking and deactivation of a mesoporous Ni–CaO–ZrO2 catalyst in dry reforming of methane: a study under different feeding compositions. Fuel 143:527–535. https://doi.org/10.1016/J.FUEL.2014.11.09710.1016/J.FUEL.2014.11.097 ↗
44. Wang X, Qiu Z, Liu Q, Chen X, Tao S, Shi C, Pang M, Liang C (2017) Heterogeneous catalytic transfer partial-hydrogenation with formic acid as hydrogen source over the Schiff-base modified gold nano-catalyst. Catal Lett 147:517–524. https://doi.org/10.1007/s10562-016-1929-910.1007/s10562-016-1929-9 ↗
45. Wilcoxon JP, Abrams BL (2006) Synthesis, structure and properties of metal nanoclusters. Chem Soc Rev 35:1162–1194. https://doi.org/10.1039/b517312b10.1039/b517312b ↗
46. Yuzik-Klimova EY, Kuchkina NV, Sorokina SA, Morgan DG, Boris B, Nikoshvili LZ, Lyubimova NA, Matveeva VG, Sulman EM, Stein BD, Mahmoud WE, Al-Ghamdi AA, Kostopoulou A, Lappas A, Shifrina ZB, Bronstein LM (2014) Magnetically recoverable catalysts based on polyphenylenepyridyl dendrons and dendrimers. RSC Adv 4:23271. https://doi.org/10.1039/c4ra00878b10.1039/c4ra00878b ↗