“Doing More with Less”: Ni(II)@ORMOSIL, a Novel Sol-Gel Pre-Catalyst for the Reduction of Nitrobenzene
Abstract
:1. Introduction
2. Results and Discussion
2.1. Catalyst Characterization
2.1.1. ZVI@ORMOSIL Characterization
2.1.2. Ni(II)@ORMOSIL Characterization
2.2. Catalytic Reduction of Nitrobenzene
2.2.1. ZVI@ORMOSIL Catalyzed Reduction of Nitrobenzene with NaBH4
2.2.2. 1.0%. Ni@ORMOSIL Reduction of Nitrobenzene
1.0%. Ni@ORMOSIL Nitrobenzene Reduction with NaBH4 in Different Reaction Media
0.2%. and 0.1% Ni(II)@ORMOSIL Reduction of Nitrobenzene with NaBH4
NiCl2 as a Catalyst for the Reduction of NB by NaBH4 in Homogeneous Media
2.2.3. 1%. Ni(II)@ORMOSIL Catalyst Stability
2.2.4. Mechanistic Analysis of NB Reduction
Catalytic Reductions by M0
Catalytic Reductions by Ni2+aq
3. Materials and Methods
3.1. Materials
3.2. Catalyst Preparation
3.2.1. 1.0%. mol Loading of ZVI@ORMOSIL
3.2.2. 1.0%. mol Loading of Ni(II)@ORMOSIL Pre-Catalyst
3.3. Catalyst Characterization
3.4. Catalytic Tests
3.4.1. Nitrobenzene Reductions with 1% ZVI@ORMOSIL
3.4.2. Nitrobenzene Reductions with 1%, 0.2% and 0.1% Ni(II)@ORMOSIL
3.4.3. Nitrobenzene Homogenous Reductions with NiCl2∙6H2O
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
- Ju, K.S.; Parales, R.E. Nitroaromatic Compounds, from Synthesis to Biodegradation. Microbiol. Mol. Biol. Rev. 2010, 74, 250–272. [Google Scholar] [CrossRef] [Green Version]
- Arora, P.K.; Bae, H. Toxicity and Microbial Degradation of Nitrobenzene, Monochloronitrobenzenes, Polynitrobenzenes, and Pentachloronitrobenzene. J. Chem. 2014, 2014, 265140. [Google Scholar] [CrossRef] [Green Version]
- Zhao, Q.J.; Hsu, C.H. Nitrobenzene. In Encyclopedia of Toxicology, 3rd ed.; Wexler, P., Ed.; Academic Press: Cambridge, MA, USA, 2014; pp. 536–539. [Google Scholar] [CrossRef]
- World Health Organization. Guidelines for Drinking-Water Quality, 4th ed. 1st Add. 2017. ISBN 9789241549950. Available online: https://apps.who.int/iris/handle/10665/254637 (accessed on 8 March 2021).
- Guy, R.C. Nitrobenzene. In Encyclopedia of Toxicology, 2nd ed.; Wexler, P., Ed.; Elsevier: Amsterdam, The Netherlands, 2005; pp. 236–238. [Google Scholar] [CrossRef]
- Cave, M.; Falkner, K.C.; McClain, C. Occupational and Environmental Hepatotoxicity. In Zakim and Boyer’s Hepatology, 6th ed.; Sanyal, A., Ed.; Elsevier: Amsterdam, The Netherlands, 2012; pp. 476–492. [Google Scholar] [CrossRef]
- Wu, L. Dilemmas downstream from the Songhua River spill. J. Med. Toxicol. 2006, 2, 112–113. [Google Scholar] [CrossRef] [Green Version]
- Zhao, Y.; Lin, L.; Hong, M. Nitrobenzene contamination of groundwater in a petrochemical industry site. Front. Environ. Sci. Eng. 2019, 13, 29. [Google Scholar] [CrossRef]
- Zhang, W.; Chen, L.; Chen, H.; Xia, S.Q. The effect of Fe0/Fe2+/Fe3+ on nitrobenzene degradation in the anaerobic sludge. J. Hazard. Mater. 2007, 143, 57–64. [Google Scholar] [CrossRef]
- Zhang, D.; Shen, J.; Shi, H.; Su, G.; Jiang, X.; Li, J.; Liu, X.; Mu, Y.; Wang, L. Substantially enhanced anaerobic reduction of nitrobenzene by biochar stabilized sulfide-modified nanoscale zero-valent iron: Process and mechanisms. Environ. Int. 2019, 131, 105020. [Google Scholar] [CrossRef]
- Huang, Y.H.; Zhang, T.C. Reduction of nitrobenzene and formation of corrosion coatings in zerovalent iron systems. Water Res. 2006, 40, 3075–3082. [Google Scholar] [CrossRef] [PubMed]
- Meyerstein, D.; Adhikary, J.; Burg, A.; Shamir, D.; Albo, Y. Zero-valent iron nanoparticles entrapped in SiO2 sol-gel matrices: A catalyst for the reduction of several pollutants. Catal. Commun. 2019, 133, 105819. [Google Scholar] [CrossRef]
- Meistelman, M.; Meyerstein, D.; Bardea, A.; Burg, A.; Shamir, D.; Albo, Y. Reductive Dechlorination of Chloroacetamides with NaBH4 Catalyzed by Zero Valent Iron, ZVI, Nanoparticles in ORMOSIL Matrices Prepared via the Sol-Gel Route. Catalysts 2020, 10, 986. [Google Scholar] [CrossRef]
- Pasinszki, T.; Krebsz, M. Synthesis and Application of Zero-Valent Iron Nanoparticles in Water Treatment, Environmental Remediation, Catalysis, and Their Biological Effects. Nanomaterials 2020, 10, 917. [Google Scholar] [CrossRef]
- Setamdideh, D.; Khezri, B. Rapid and Efficient Reduction of Nitroarenes to Their Corresponding Amines with Promotion of NaBH4/NiCl2·6H2O System in Aqueous CH3CN. Chem. Asian J. 2010, 22, 5575–5580. [Google Scholar]
- Zeynizadeh, B.; Sorkhabi, S. Fast and efficient protocol for solvent-free reduction of nitro compounds to amines with NaBH4 in the presence of Bis-thiourea complexes of bivalent cobalt nickel, copper and zinc chlorides. J. Chem. Soc. Pak. 2016, 38, 679–684. [Google Scholar]
- Wasiak, T.; Przypis, L.; Walczak, K.Z.; Janas, D. Nickel Nanowires: Synthesis, Characterization and Application as Effective Catalysts for the Reduction of Nitroarenes. Catalysts 2018, 8, 566. [Google Scholar] [CrossRef] [Green Version]
- Ibraheem, H.H.; El-Mekkaw, D.M.; Hassan, S.A.; Selim, M.M. Innovative Method for the Reduction of Nitrophenols Using Nickel Nanocatalysts in Zeolite-Y Prepared from Egyptian Kaolin. Egypt. J. Chem. 2010, 53, 565–579. [Google Scholar] [CrossRef]
- Feng, J.; Wang, Q.; Fan, D.; Ma, L.; Jiang, D.; Xie, J.; Zhu, J. Nickel-based xerogel catalysts: Synthesis via fast sol-gel method and application in catalytic hydrogenation of p-nitrophenol to p-aminophenol. Appl. Surf. Sci. 2016, 382, 135–143. [Google Scholar] [CrossRef]
- Burg, A.; Wolfer, Y.; Shamir, D.; Kornweitz, H.; Albo, Y.; Maimon, E. Meyerstein The role of carbonate in electro-catalytic water oxidation by using Ni(1,4,8,11-tetraazacyclotetradecane)2+ D. Dalton Trans. 2017, 46, 10774–10779. [Google Scholar] [CrossRef]
- Adhikary, J.; Meyerstein, D.; Marks, V.; Meistelman, M.; Gershinsky, G.; Burg, A.; Shamir, D.; Kornweitz, H.; Albo, Y. Sol-gel entrapped Au0- and Ag0-nanoparticles catalyze reductive de-halogenation of halo-organic compounds by BH4−. Appl. Catal. B 2018, 239, 450–462. [Google Scholar] [CrossRef]
- Basha, M.A.F. Optical properties and colorimetry of gelatine gels prepared in different saline solutions. J. Adv. Res. 2018, 16, 55–65. [Google Scholar] [CrossRef] [PubMed]
- Mack, H.; Reisfeld, R.; Avnir, D. Fluorescence of rare earth ions adsorbed on porous vycor glass. Chem. Phys. Lett. 1983, 99, 238–239. [Google Scholar] [CrossRef]
- Levy, D.; Reisfeld, R.; Avnir, D. Fluorescence of europium(III) trapped in silica gel-glass as a probe for cation binding and for changes in cage symmetry during gel dehydration. Chem. Phys. Lett. 1984, 109, 593–597. [Google Scholar] [CrossRef]
- Wezynfeld, N.; Goch, E.W.; Bal, W.; Fraczyk, T. cis-Urocanic acid as a potential nickel(ii) binding molecule in the human skin. Dalton Trans. 2014, 43, 3196–3201. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Takahashi, R.; Sato, S.; Sodesawa, T.; Kamomae, Y. Measurement of the diffusion coefficient of nickel nitrate in wet silica gel using UV/VIS spectroscope equipped with a flow cell. Phys. Chem. Chem. Phys. 2000, 2, 1199–1204. [Google Scholar] [CrossRef]
- Hantsche, H. Comparison of basic principles of the surface-specific analytical methods: AES/SAM, ESCA (XPS), SIMS, and ISS with X-ray microanalysis, and some applications in research and industry. Scanning 1989, 11, 257–280. [Google Scholar] [CrossRef]
- Shard, A.G. Detection limits in XPS for more than 6000 binary systems using Al and Mg Kα X-rays. Surf. Interface Anal. 2014, 46, 175–185. [Google Scholar] [CrossRef]
- Das, U.; Zhang, G.; Hu, B.; Hock, A.S.; Redfern, P.C.; Miller, J.T.; Curtiss, L.A. Effect of Siloxane Ring Strain and Cation Charge Density on the Formation of Coordinately Unsaturated Metal Sites on Silica: Insights from Density Functional Theory (DFT) Studies. ACS Catal. 2015, 5, 7177–7185. [Google Scholar] [CrossRef]
- Nimir, H.I.; Hamza, A.; Ibnelwaleed, A.H. Development of Greener D-Metal Inorganic Crosslinkers for Polymeric Gels Used in Water Control in Oil and Gas Applications. Energies 2020, 13, 4262. [Google Scholar] [CrossRef]
- Livage, J.; Henry, M.; Sanchez, C. Sol-gel chemistry of transition metal oxides. Prog. Solid. State Chem. 1988, 18, 259–341. [Google Scholar] [CrossRef]
- Hannauer, J.; Demirci, U.B.; Geantet, C.; Herrmann, J.M.; Miele, P. Enhanced hydrogen release by catalyzed hydrolysis of sodium borohydride–ammonia borane mixtures: A solution-state 11B NMR study. Phys. Chem. Chem. Phys. 2011, 13, 3809–3818. [Google Scholar] [CrossRef] [PubMed]
- Vijay, A.K.; Meyerstein, D.; Marks, V.; Albo, Y. Kinetics of the reaction of H2 with Pt0-nanoparticles in aqueous suspensions monitored by the catalytic reduction of PW12O403−. Inorg. Chem. Front. 2021, 8, 989–995. [Google Scholar] [CrossRef]
- Tang, X.; Jiang, Z.; Li, Z.; Gao, Z.; Bai, Y.; Zhao, S.; Feng, J. The effect of the variation in material composition on the heterogeneous pore structure of high-maturity shale of the Silurian Longmaxi formation in the southeastern Sichuan Basin, China. J. Nat. Gas Sci. Eng. 2015, 23, 464–473. [Google Scholar] [CrossRef]
- Thommes, M.; Kaneko, K.; Neimark, A.V.; Olivier, J.P.; Rodriguez-Reinoso, F.; Rouquerol, J.; Sing, K.S.W. Physisorption of gases, with special reference to the evaluation of surface area and pore size distribution. Pure Appl. Chem. 2015, 87, 1–19. [Google Scholar] [CrossRef] [Green Version]
- Hansen, T.W.; DeLaRiva, A.T.; Challa, S.R.; Datye, A.K. Sintering of Catalytic Nanoparticles: Particle Migration or Ostwald Ripening? Acc. Chem. Res. 2013, 46, 1720–1730. [Google Scholar] [CrossRef]
- Jeromenok, J.; Weber, J. Restricted Access: On the Nature of Adsorption/Desorption Hysteresis in Amorphous, Microporous Polymeric Materials. Langmuir 2013, 29, 12982–12989. [Google Scholar] [CrossRef] [PubMed]
- Adhikary, J.; Meistelman, M.; Burg, A.; Shamir, D.; Meyerstein, D.; Albo, Y. The Reductive De-halogenations of Mono and Tribromo Acetic Acids by NaBH4 Catalysed by Gold Nanoparticles Entrapped in Sol-Gel Matrices Follow Different Pathways. Eur. J. Inorg. Chem. 2017, 2017, 1510–1515. [Google Scholar] [CrossRef]
- Trabelsi, K.; Meistelman, M.; Ciriminna, R.; Albo, Y.; Pagliaro, M. Effective and Green Removal of Trichloroacetic Acid from Disinfected Water. Materials 2020, 13, 827. [Google Scholar] [CrossRef] [Green Version]
- Song, J.; Huang, Z.F.; Pan, L.; Li, K.; Zhang, X.; Wang, L.; Zou, J.J. Review on selective hydrogenation of nitroarene by catalytic, photocatalytic and electrocatalytic reactions. Appl. Cat. B 2018, 227, 386–408. [Google Scholar] [CrossRef]
- Qin, C.; Zhang, J.; Zhang, C.; He, Y.; Tratnyek, P.G. Abiotic Transformation of Nitrobenzene by Zero Valent Iron under Aerobic Conditions: Relative Contributions of Reduction and Oxidation in the Presence of Ethylene Diamine Tetraacetic Acid. Environ. Sci. Technol. 2021, 55, 6828–6837. [Google Scholar] [CrossRef]
- Machado, S.A.S.; Avaca, L.A. The hydrogen evolution reaction on nickel surfaces stabilized by H-absorption. Electrochim. Acta 1994, 39, 1385–1391. [Google Scholar] [CrossRef]
- He, F.; Gong, L.; Fan, D.; Tratnyek, P.G.; Lowry, G.V. Quantifying the efficiency and selectivity of organohalide dechlorination by zerovalent iron. Environ. Sci. Process. Impacts 2020, 22, 528–542. [Google Scholar] [CrossRef] [PubMed]
- Agrawal, A.; Tratnyek, P.G. Reduction of Nitro Aromatic Compounds by Zero-Valent Iron Metal. Environ. Sci. Technol. 1995, 30, 153–160. [Google Scholar] [CrossRef]
- Bae, S.; Gim, S.; Kim, H.; Hanna, K. Effect of NaBH4 on properties of nanoscale zero-valent iron and its catalytic activity for reduction of p-nitrophenol. Appl. Cat. B 2016, 182, 541–549. [Google Scholar] [CrossRef]
- Andreou, D.; Iordanidou, D.; Tamiolakis, I.; Armatas, G.S.; Lykakis, I.N. Reduction of Nitroarenes into Aryl Amines and N-Aryl hydroxylamines via Activation of NaBH4 and Ammonia-Borane Complexes by Ag/TiO2 Catalyst. Nanomaterials 2016, 6, 54. [Google Scholar] [CrossRef] [Green Version]
- Abdelhamid, H.N. A review on hydrogen generation from the hydrolysis of sodium borohydride. Int. J. Hydrog. Energy 2021, 46, 726–765. [Google Scholar] [CrossRef]
- Karimadom, B.R.; Meyerstein, D.; Kornweitz, H. Calculating the adsorption energy of a charged adsorbent in a periodic metallic system—The case of BH4− hydrolysis on Ag(111) surface. Phys. Chem. Chem. Phys. 2021. [Google Scholar] [CrossRef]
- Sermiagin, A.; Meyerstein, D.; Bar-Ziv, R.; Zidki, T. The Chemical Properties of Hydrogen Atoms Adsorbed on M°- Nanoparticles Suspended in Aqueous Solutions: The Case of Ag°-NPs and Au°-NPs Reduced by BD4−. Angew. Chem. Int. Ed. 2018, 57, 16525. [Google Scholar] [CrossRef]
- Mondal, T.; Sermiagin, A.; Meyerstein, D.; Zidki, T.; Kornweitz, H. On the mechanism of reduction of M(H2O)mn+ by borohydride: The case of Ag(H2O)2+. Nanoscale 2020, 12, 1657–1672. [Google Scholar] [CrossRef]
- Rolly, G.S.; Meyerstein, D.; Yardeni, G.; Bar-Ziv, R.; Zidki, T. New insights into HER catalysis: The effect of nano-silica support on catalysis by silver nanoparticles. Phys. Chem. Chem. Phys. 2020, 22, 6401–6405. [Google Scholar] [CrossRef] [PubMed]
- Gu, C.; Jia, H.; Li, H.; Teppen, B.J.; Boyd, S.A. Synthesis of highly reactive subnano-sized Zero-Valent Iron using smectite clay templates. Environ. Sci. Technol. 2010, 44, 4258–4263. [Google Scholar] [CrossRef] [Green Version]
Sample | BET Surface (m2/g) | Average Pore Volume (cm3/g) | Average Pore Diameter (nm) |
---|---|---|---|
Ni(II)@ORMOSIL no reduction | 602 | 0.34 | 3.6 |
Ni(II)@ORMOSIL reduced and re-oxidized | 660 | 0.38 | 3.6 |
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. |
© 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
Share and Cite
Meistelman, M.; Meyerstein, D.; Burg, A.; Shamir, D.; Albo, Y. “Doing More with Less”: Ni(II)@ORMOSIL, a Novel Sol-Gel Pre-Catalyst for the Reduction of Nitrobenzene. Catalysts 2021, 11, 1391. https://doi.org/10.3390/catal11111391
Meistelman M, Meyerstein D, Burg A, Shamir D, Albo Y. “Doing More with Less”: Ni(II)@ORMOSIL, a Novel Sol-Gel Pre-Catalyst for the Reduction of Nitrobenzene. Catalysts. 2021; 11(11):1391. https://doi.org/10.3390/catal11111391
Chicago/Turabian StyleMeistelman, Michael, Dan Meyerstein, Ariela Burg, Dror Shamir, and Yael Albo. 2021. "“Doing More with Less”: Ni(II)@ORMOSIL, a Novel Sol-Gel Pre-Catalyst for the Reduction of Nitrobenzene" Catalysts 11, no. 11: 1391. https://doi.org/10.3390/catal11111391