Abstract
Alumina, silica, and fumed silica systems with anchored Ni and Mn active species were produced and the catalytic activity has been studied for nitrile hydration. The powdered sample of the catalysts were treated with heat at 400 and 750 °C after being produced by the chemical impregnation method. The resultant materials were analyzed by powder XRD, FTIR, FESEM, HRTEM, XPS, UV-Vis-DRS, N2 adsorption, H2-TPR and NH3-TPD techniques. The effect of the calcination temperature, the nature of the support and the content of Mn were examined and the catalytic performance of the systems was evaluated. The initial investigation with 2-cyanopyridine as the reactant discovered that materials with 5.0 wt.% of Mn exhibited increased activity among all obtained samples, depending on the supports and the calcination temperature. The FS-400 samples showed the selective conversion to amide in a shorter duration and the FS5-400 catalyst outperformed the others in 1 h duration. It suggests that the entire conversion occurred in less amount of time as a result of the catalyst's greater surface area, higher dispersion, and efficient diffusion. The optimized system with a relatively low content of transition metals presented remarkable activity for the application of controlled hydration of nitriles.
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References
Liu L, Corma A (2018) Metal catalysts for heterogeneous catalysis: from single atoms to nanoclusters and nanoparticles. Chem Rev 118:4981–5079
Zaera F (2021) Molecular approaches to heterogeneous catalysis. Coord Chem Rev 448:214179
Poovan F, Chandrashekhar VG, Natte K, Jagadeesh RV (2022) Synergy between homogeneous and heterogeneous catalysis. Catal Sci Techmol 12:6623–6649
Yan P, Bryant G, Meng-Jung M, Mensah J, Kennedy E, Stockenhuber M (2020) Shape selectivity of zeolite catalysts for the hydrodeoxygenation of biocrude oil and its model compounds. Microporous Mesoporous Mater 309:110561
Ali H, Vandevyvere T, Lauwaert J, Kansal SK, Sabbe MK, Saravanamurugan S, Thybaut JW (2023) Enhancing the anisole hydrodeoxygenation activity over Ni/Nb2O5-x by tuning the oxophilicity of the support. Catal Sci technol 13:1140–1153
Magg N, Immaraporn B, Giorgi JB, Schroeder T, Bäumer M, Döbler J, Wu Z, Kondratenko E, Cherian M, Baerns M, Stair PC (2004) Vibrational spectra of alumina-and silica-supported vanadia revisited: an experimental and theoretical model catalyst study. J Catal 226:88–100
Chen Y, Zhang L (1992) Surface interaction model of γ-alumina-supported metal oxides. Catal Lett 12:51–62
Marcé P, Lynch J, Blacker AJ, Williams JMJ (2016) A mild hydration of nitriles catalysed by copper (II) acetate. Chem Commun 52:1436–1438
Djoman MCKB, Ajjou AN (2000) The hydration of nitriles catalyzed by water-soluble rhodium complexes. Tetrahedron Lett 41:4845–4849
Breno KL, Pluth MD, Tyler DR (2003) Organometallic chemistry in aqueous solution. hydration of nitriles to amides catalyzed by a water-soluble molybdocene, (MeCp)2Mo(OH)(H2O)+. Organometallics 22:1203–1211
Goto A, Naka H, Nyoji R, Saito S (2011) One-pot nitrile aldolization/hydration operation giving β-hydroxy carboxamides. Chem Asian J 6:1740–1743
Goto A, Endo K, Saito S (2008) RhI-catalyzed hydration of organonitriles under ambient conditions. Angew Chem Int Ed 47:3607–3609
Ramon RS, Marion N, Nolan SP (2009) Gold activation of nitriles: catalytic hydration to amides. Chem Eur J 15:8695–8697
Liu KT, Shih MH, Huang HW, Hu CJ (1988) Catalytic hydration of nitriles to amides with manganese dioxide on silica gel. Synthesis 9:715–717
Bazi F, Badaoui HE, Tamani S, Sokori S, Solhy A, Macquarrie DJ, Sebti S (2006) A facile synthesis of amides by selective hydration of nitriles using modified natural phosphate and hydroxyapatite as new catalysts. Appl Catal A: Gen 301:211–214
Tamura M, Wakasugi H, Shimizu K, Satsuma A (2011) Efficient and substrate-specific hydration of nitriles to amides in water by using a CeO2 catalyst. Chem Eur J 17:11428–11432
Yamaguchi K, Matsushita M, Mizuno N (2004) Efficient hydration of nitriles to amides in water catalyzed by ruthenium hydroxide supported on alumina. Angew Chem Int Ed 43:1576–1580
Kim AY, Bae HS, Park S, Park S, Park KH (2011) Silver nanoparticle catalyzed selective hydration of nitriles to amides in water under neutral conditions. Catal Lett 141:685–690
Subramanian T, Pitchumani K (2012) An efficient hydration of nitriles to amides in aqueous media by hydrotalcite-clay supported nickel nanoparticles. Catal Commun 29:109–113
Mitsudome T, Mikami Y, Mori H, Arita S, Mizugaki T, Jitsukawa K, Kaneda K (2009) Supported silver nanoparticle catalyst for selective hydration of nitriles to amides in water. Chem Commun 22:3258–3260
Thirukovela NS, Balaboina R, Kankala S, Vadde R, Vasam CS (2019) Activation of nitriles by silver (I) N-heterocyclic carbenes: an efficient on-water synthesis of primary amides. Tetrahedron 75:2637–2641
Salam N, Kundu SK, Molla RA, Mondal P, Bhaumik A, Islam SM (2014) Ag-grafted covalent imine network material for one-pot three-component coupling and hydration of nitriles to amides in aqueous medium. RSC Adv 88:47593–47604
Ghosh K, Iqubal MA, Molla RA, Mishra A, Islam SM (2015) Direct oxidative esterification of alcohols and hydration of nitriles catalyzed by a reusable silver nanoparticle grafted onto mesoporous polymelamine formaldehyde (AgNPs@ mPMF). Catal Sci Technol 5:1606–1622
Zhang S, Xu H, Lou C, Senan AM, Chen Z, Yin G (2017) Efficient bimetallic catalysis of nitrile hydration to amides with a simple Pd(OAc)2/Lewis acid catalyst at ambient temperature. Eur J Org Chem 14:1870–1875
Liu YM, He L, Wang MM, Cao Y, He HY, Fan KN (2012) A general and efficient heterogeneous gold-catalyzed hydration of nitriles in neat water under mild atmospheric conditions. Chem Sus Chem 5:1392–1396
Thenmozhi S, Kadirvelu K (2018) Transfer hydrogenation and hydration of aromatic aldehydes and nitriles using heterogeneous NiO nanofibers as a catalyst. New J Chem 42:15572–15577
Baig RBN, Varma RS (2012) A facile one-pot synthesis of ruthenium hydroxide nanoparticles on magnetic silica: aqueous hydration of nitriles to amides. Chem Commun 48:6220–6222
Joshi H, Sharma KN, Sharma AK, Prakash O, Kumar A, Singh AK (2014) Magnetite nanoparticles coated with ruthenium via SePh layer as a magnetically retrievable catalyst for the selective synthesis of primary amides in an aqueous medium. Dalton Trans 43:12365–12372
Woo H, Lee K, Park S, Park KH (2014) Magnetically separable and recyclable Fe3O4-supported Ag nanocatalysts for reduction of nitro compounds and selective hydration of nitriles to amides in water. Molecules 19:699–712
Shimizu KI, Imaiida N, Sawabe K, Satsuma A (2012) Hydration of nitriles to amides in water by SiO2-supported Ag catalysts promoted by adsorbed oxygen atoms. Appl Catal A: Gen 421:114–120
Manrique E, Ferrer I, Lu C, Fontrodona X, Rodríguez M, Romero I (2019) A heterogeneous ruthenium dmso complex supported onto silica particles as a recyclable catalyst for the efficient hydration of nitriles in aqueous medium. Inorg Chem 58:8460–8470
Cao F, Xiang J, Su S, Wang P, Hu S, Sun L (2015) Ag modified Mn-Ce/γ-Al2O3 catalyst for selective catalytic reduction of NO with NH3 at low-temperature. Fuel Process Technol 135:66–72
Thirupathi B, Smirniotis PG (2012) Nickel-doped Mn/TiO2 as an efficient catalyst for the low-temperature SCR of NO with NH3: catalytic evaluation and characterizations. J Catal 288:74–83
Liu C, Shi JW, Gao C, Niu C (2016) Manganese oxide-based catalysts for low-temperature selective catalytic reduction of NOx with NH3: a review. Appl Catal A: Gen 522:54–69
Yamaguchi K, Wang Y, Kobayashi H, Mizuno N (2012) Efficient hydration of nitriles promoted by simple amorphous manganese oxide using reduced amounts of water. Chem Lett 41:574–576
Battilocchio C, Hawkins JM, Ley SV (2014) Mild and selective heterogeneous catalytic hydration of nitriles to amides by flowing through manganese dioxide. Org Lett 16:1060–1063
Gangarajula Y, Gopal B (2014) Investigation of nano NiO, supported and metal ion substituted NiO for selective hydration of aromatic nitriles to amides. Appl Catal A: Gen 475:211–217
Pérez H, Navarro P, Delgado JJ, Montes M (2011) Mn-SBA15 catalysts prepared by impregnation: influence of the manganese precursor. Appl Catal A: Gen 400:238–248
Yurdakal S, Garlisi C, Özcan L, Bellardita M, Palmisano G (2019) In: Marcì G, Palmisano L (eds) Heterogeneous photocatalysis: Relationships with heterogeneous catalysis and perspectives, 1st edn. Elsevier, Netherlands
Tang W, Yao M, Deng Y, Li X, Han N, Wu X, Chen Y (2016) Decoration of one-dimensional MnO2 with Co3O4 nanoparticles: a heterogeneous interface for remarkably promoting catalytic oxidation activity. Chem Eng J 306:709–718
Tang W, Deng Y, Li W, Li S, Wu X, Chen Y (2015) Restrictive nanoreactor for growth of transition metal oxides (MnO2, Co3O4, NiO) nanocrystal with enhanced catalytic oxidation activity. Catal Commun 72:165–169
Deng Y, Tang W, Li W, Chen Y (2018) MnO2-nanowire@ NiO-nanosheet core-shell hybrid nanostructure derived interfacial effect for promoting catalytic oxidation activity. Catal Today 308:58–63
Malik M, Chan KH, Azimi G (2021) Quantification of nickel, cobalt, and manganese concentration using ultraviolet-visible spectroscopy. RSC Adv 11(45):28014–28028
Saravanakumar K, Muthuraj V, Vadivel S (2016) Constructing novel Ag nanoparticles anchored on MnO2 nanowires as an efficient visible light driven photocatalyst. RSC Adv 6(66):61357–61366
Tang W, Wu X, Li D, Wang Z, Liu G, Liu H, Chen Y (2014) Oxalate route for promoting activity of manganese oxide catalysts in total VOCs’ oxidation: effect of calcination temperature and preparation method. J Mater Chem A 2:2544–2554
Zhang X, Li H, Hou F, Yang Y, Dong H, Liu N, Wang Y, Cui L (2017) Synthesis of highly efficient Mn2O3 catalysts for CO oxidation derived from Mn-MIL-100. Appl Surf Sci 411:27–33
Pereira JDA, Lacerda JN, Coelho IF, Nogueira C de SC, Franceschini DF, Ponzio EA, Mainier FB, Xing Y (2020) Tuning the morphology of manganese oxide nanostructures for obtaining both high gravimetric and volumetric capacitance. Mater Adv 1(7):2433–2442
Wang M, Chen K, Liu J, He Q, Li G, Li F (2018) Efficiently enhancing electrocatalytic activity of α-MnO2 nanorods/N-doped ketjenblack carbon for oxygen reduction reaction and oxygen evolution reaction using facile regulated hydrothermal treatment. Catalysts 8(4):138
Sun X, Hao Z, Nan H, Xu J, Tian H (2021) Silver decorated lanthanum calcium manganate for electrochemical supercapacitor. Mater Res Express 8(7):075502
Huang W, Ding S, Chen Y, Hao W, Lai X, Peng J, Tu J, Cao Y, Li X (2017) 3D NiO hollow sphere/reduced graphene oxide composite for high-performance glucose biosensor. Sci Rep 7:5220
Raza MH, Movlaee K, Leonardi SG, Barsan N, Neri G, Pinna N (2020) Gas sensing of NiO-SCCNT core-shell heterostructures: optimization by radial modulation of the hole-accumulation layer. Adv Funct Mater 30:1906874
de Jesús JC, Carrazza J, Pereira P, Zaera F (1998) Hydroxylation of NiO films: the effect of water and ion bombardment during the oxidation of nickel foils with O2 under vacuum. Surf Sci 397:34–47
Salunkhe P, AV MA, Kekuda D (2021) Structural, spectroscopic and electrical properties of dc magnetron sputtered NiO thin films and an insight into different defect states. Appl Phys A 127(5):390
Malloy P, Browning GJ, Donne SW (2005) Surface characterization of heat-treated electrolytic manganese dioxide. J Colloid Interface Sci 285:653–664
Kukushkin VY, Pombeiro AJ (2005) Metal-mediated and metal-catalyzed hydrolysis of nitriles. Inorg Chim Acta 358:1–21
Acknowledgements
The authors gratefully acknowledge, this research work was supported by Vellore Institute of Technology (Vellore) and the Basic Science Research Program through the National Research Foundation of Korea (NRF), funded by the Ministry of Education (2020R1I1A3052258) for financial support. In addition, the work was funded by the Researchers Supporting Project Number (RSP2023R243) King Saud University, Riyadh, Saudi Arabia.
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Devi Govindaraj: Conceptualization, Investigation, Writing – original draft; Raja Venkatesan: Conceptualization, Investigation, Formal analysis, Writing – original draft; Seong-Cheol Kim: Supervision, Funding acquisition, Project administration, Writing – review & editing; Asma A. Alothman: Formal analysis, Data curation; Buvaneswari Gopal: Conceptualization, Supervision, Writing – review & editing. All authors read and approved the final manuscript.
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Govindaraj, D., Venkatesan, R., Kim, SC. et al. Fumed Silica Support as a Catalytic Platform, Ni and Mn Oxide Reactive Species for the Selective Hydration of Aromatic Nitriles. Silicon 16, 853–866 (2024). https://doi.org/10.1007/s12633-023-02716-9
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DOI: https://doi.org/10.1007/s12633-023-02716-9