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Efficient reduction of aromatic nitro compounds catalyzed by nickel chloride supported on natural phosphate

Abderrahim Baba, Hicham Ouahbi, Ayoub Hassine, Jalila Sebti, Laila Laasri, Said Sebti

Abstract


Natural phosphates are an important natural resource in Morocco, which need to be valorized; they can be used not only as primary raw material to produce the fertilizers but also as catalysts. In this work, we have prepared natural phosphate-supported nickel chloride (NiCl2/NP). This material was effectively used as a heterogeneous catalyst in the presence of sodium borohydride as a reducing agent. The reaction was carried out at room temperature in an aqueous medium. The catalyst showed an excellent activity for the reduction of aromatic nitro compounds under simple conditions along with good usability.


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- B. M. Trost, I. Fleming, Comprehensive organic synthesis: Reduction, Eds., Pergamon: Oxford, 1991, 8, 1139p.

- G. W. Kabalka, R. S. Varma, Reduction of nitro and nitroso compounds, In Comprehensive Organic Synthesis, B. M. Trost, I. Fleming, Eds., Pergamon: Oxford, 1991, 8, 363–377.

- R. J. Kalbasi, A. A. Nourbakhsh, F. Babaknezhad, Synthesis and characterization of Ni nanoparticles-polyvinylamine/sba-15 catalyst for simple reduction of aromatic nitro compounds, Catal. Commun., 2011, 12, 955–960.

- F. Zamani, S. Kianpour, Fast and efficient reduction of nitro aromatic compounds over Fe3O4/β-alanine-acrylamide-Ni nanocomposite as a new magnetic catalyst, Catal. Commun., 2014, 45, 1–6.

- R. J. Kalbasi, F. Zamani, Synthesis and characterization of Ni nanoparticles incorporated into hyperbranched polyamidoamine-polyvinylamine/sba-15 catalyst for simple reduction of nitro aromatic compounds, RSC Adv., 2014, 4, 7444–7453.

- S. Dayan, F. Arslan, N. Kalaycioglu Ozpozan, Ru (II) impregnated Al2O3, Fe3O4, SiO2 and N-coordinate ruthenium (II) arene complexes: Multifunctional catalysts in the hydrogenation of nitroarenes and the transfer hydrogenation of aryl ketones, Appl. Catal. B, 2015, 164, 305–315.

- J. F. de Souza, G. T. da Silva, A. R. Fajardo, Chitosan-based film supported copper nanoparticles: A potential and reusable catalyst for the reduction of aromatic nitro compounds, Carbohyd. Polym., 2017, 161, 187–196.

- A. Khorshidi, B. Ghorbannezhad, A highly effective ag-Raney nickel hybrid catalyst for reduction of nitrofurazone and aromatic nitro compounds in aqueous solution, RSC Advances, 2017, 7, 29938–29943.

- Y. Liu, M. Guerrouache, S. I. Kebe, B. Carbonnier, B. Le Droumaguet, Gold nanoparticles-supported histamine-grafted monolithic capillaries as efficient microreactors for flow-through reduction of nitro-containing compounds, J. Mater. Chem. A, 2017, 5, 11805–11814.

- B. Zeynizadeh, I. Mohammadzadeh, Z. Shokri, S. Ali Hosseini, Synthesis and characterization of NiFe2O4@Cu nanoparticles as a magnetically recoverable catalyst for reduction of nitroarenes to arylamines with NaBH4, J. Colloid Interf. Sci., 2017, 500, 285–293.

- S. Sebti, A. Saber, A. Rhihil, R. Nazih, R. Tahir, Claisen–Schmidt condensation catalysis by natural phosphate, Appl. Catal. A, 2001, 206, 217–220.

- H. El Badaoui, F. Bazi, S. Tamani, S. Boulaajaj, M. Zahouily, H. B. Lazrek, S. Sebti, Lewis acid–doped natural phosphate: New catalysts for the one‐pot synthesis of 3,4‐dihydropyrimdin‐2(1H)‐one, Synth. Commun., 2005, 35, 2561–2568.

- F. Bazi, H. El Badaoui, S. Tamani, S. Sokori, A. Solhy, D. Macquarrie, S. Sebti, A facile synthesis of amides by selective hydration of nitriles using modified natural phosphate and hydroxyapatite as new catalysts, Appl. Catal. A, 2006, 301, 211–214.

- A. Hassine, S. Sebti, A. Solhy, N. Thiebault, E. Bilal, C. Len, A. Fihri, Natural phosphate-supported palladium for hydration of aromatic nitriles to amides in aqueous medium, Curr. Org. Chem., 2016, 20, 2022–2028.

- J. Hidalgo-Carrillo, J. Sebti, M.A. Aramendía. A. Marinas, J.M. Marinas, S. Sebti, F.J. Urbano, A study on the potential application of natural phosphate in photocatalytic processes, J. Colloid Interf. Sci., 2010, 344, 475-481.

- M. Dakkach, A. Atlamsani, S. Sebti, Le phosphate natural modifié au vanadium : Un nouveau catalyseur pour l’oxydation des cycloalcanones et des α-cétols en présence de l’oxygène moléculaire, C. R. Chim, 2012, 15, 482–492.

- J. Hidalgo-Carrillo, J. Sebti, A. Marinas, J.M. Marinas, S. Sebti, F.J. Urbano, XPS evidence for structure–performance relationship in selective hydrogenation of crotonaldehyde to crotyl alcohol on platinum systems supported on natural phosphates, J. Colloid Interf. Sci., 2012, 382, 67–73.

- A. Hassine, S. Sebti, A. Solhy, M. Zahouily, C. Len, M. N. Hedhili, A. Fihri, Palladium supported on natural phosphate: Catalyst for Suzuki coupling reactions in water, Appl. Catal. A, 2013, 450, 13–18.

- A. Hassine, M. Bouhrara, S. Sebti, A. Solhy, R. Mahfouz, D. Luart, C. Len, A. Fihri, Natural phosphate-supported palladium: A highly efficient and recyclable catalyst for the Suzuki-Miyaura coupling under microwave irradiation, Curr. Org. Chem., 2014, 18, 3141–3148.

- M. O. Abba, V. M. Gonzalez-DelaCruz, G. Colón, S. Sebti, A. Caballero, In situ XAS study of an improved natural phosphate catalyst for hydrogen production by reforming of methane, Appl. Catal. B, 2014, 150–151, 459–465.

- H. Yaacoubi, O. Zidani, M. Mouflih, M. Gourai, S. Sebti, Removal of cadmium from water using natural phosphate as adsorbent, Procedia Eng., 2014, 83, 386-39.

- H. Yaacoubi, Z. Songlin, M. Mouflih, M. Gourai, S. Sebti, Adsorption isotherm, kinetic and mechanism studies of 2-nitrophenol on sedimentary phosphate, Mediterr. J. Chem., 2015, 4, 289–296.

- F. Haber, Z. Elektrochem., 1898, 22, 506–512.

- E. A. Gelder, S. D. Jackson, C. M. Lok, The hydrogenation of nitrobenzene to aniline: a new mechanism, Chem. Commun., 2005, 522-524.

- F. Alonso, P. Riente, J.A. Sirvent, M. Yus, Nickel nanoparticles in hydrogen-transfer reductions: Characterisation and nature of the catalyst, Appl. Catal. A, 2010, 378, 42-51.

- R. K. Sharma, Y. Monga, A. Puri, Magnetically separable silica@Fe3O4 core–shell supported nano-structured copper (II) composites as a versatile catalyst for the reduction of nitroarenes in aqueous medium at room temperature, J. Mol. Catal. A., 2014, 393, 84–95.

- D. Shah, H. Kaur, Resin-trapped gold nanoparticles: An efficient catalyst for reduction of nitro compounds and Suzuki-Miyaura coupling, J. Mol. Catal. A, 2014, 381, 70–76.

- G. Singh, S. Rani, A. Arora, Sanchita, H. Duggal, D. Mehta, Organic-inorganic nano-hybrid decorated by copper (II) incarceration: A versatile catalytic assembly for the swift reduction of aromatic nitro and dye compounds, Mol. Catal., 2017, 431, 15–26.

- S. Doherty, J. G. Knight, T. Backhouse, A. Bradford, F. Saunders, A. Bourne, T. W. Chamberlain, R. Stones, A. Clayton and K. Lovelock, Highly efficient aqueous phase reduction of nitroarenes catalyzed by phosphine-decorated polymer immobilized ionic liquid stabilized PdNPs, Catal. Sci. Technol., 2018, 8, 1454-1467.

- S. H. Hosseini, N. Zohreh, S. Alipour, C. Busuioc, R. Negread, Gold nanoparticles stabilized on SBA-15 functionalized NNN-pincer ligand; highly effective catalyst for reduction of nitroarenes in aqueous medium, Catal. Commun., 2018, 108, 93–97.

- S. Giri, R. Das, C. Westhuyzen, A. Maity, An efficient selective reduction of nitroarenes catalyzed by reusablesilver-adsorbed waste nanocomposite, Appl. Catal. B, 2017, 209, 669–678.

- S. Fountoulaki, V. Daikopoulou, P. L. Gkizis, I. Tamiolakis, G. S. Armatas, I. N. Lykakis, Mechanistic Studies of the Reduction of Nitroarenes by NaBH4 or Hydrosilanes Catalyzed by Supported Gold Nanoparticles, ACS Catal. 2014, 4, 3504−3511.

- Y. S. Feng, J. J. Ma, Y. M Kang, Hua-Jian Xu, PdCu nanoparticles supported on graphene: an efficient and recyclable catalyst for reduction of nitroarenes, Tetrahedron, 2014, 70, 6100-6105.

- J. Davarpanah, A. R. Kiasat, Catalytic application of silver nanoparticles immobilized to rice husk-SiO2-aminopropylsilane composite as recyclable catalyst in the aqueous reduction of nitroarenes, Catal. Commun., 2013, 41 6–11.


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