Gold nanoparticles supported on reduced graphene oxide as green catalyst for solventless hydrosilylation process
DOI:
https://doi.org/10.22452/mnij.vol3no2.2Keywords:
gold nanoparticles, reduce graphene oxide, disiloxane, solventless, dehydrogenative couplingAbstract
The hydrosilylation reaction is a versatile process that is used to synthesize a variety of organosilicon compounds. However, the traditional metal oxide catalysts used for this reaction suffer from low activity and selectivity. In this study, we synthesized and characterized a gold nanoparticles (AuNPs)-reduced graphene oxide (rGO) catalyst for the hydrosilylation reaction. The AuNPs-rGO catalyst was synthesized by a one-pot method using trisodium citrate (Na3C6H5O7) as a reducing and capping agent. The catalyst was characterized by XRD, FESEM, and FTIR. The hydrosilylation reaction was carried out under solventless conditions using dimethylphenylsilane as the substrate. The AuNPs-rGO catalyst was found to be highly active and selective for the hydrosilylation reaction, yielding a 100% conversion of the substrate to disiloxane in 3 hours. The results of this study demonstrate the potential of AuNPs-rGO catalysts for the hydrosilylation reaction and suggest that they could be used to develop more efficient and sustainable processes for the synthesis of organosilicon compounds.
References
Okuhara, T., Water-tolerant solid acid catalysts. Chemical reviews, 2002. 102(10): p. 3641-3666.
Hattori, H., Solid base catalysts: generation of basic sites and application to organic synthesis. Applied Catalysis A: General, 2001. 222(1-2): p. 247-259.
Chiusoli, G.P. and P.M. Maitlis, Metal-catalysis in industrial organic processes. 2019: Royal Society of Chemistry.
Mashayekhi, N.A., M.C. Kung, and H.H. Kung, Selective oxidation of hydrocarbons on supported Au catalysts. Catalysis Today, 2014. 238: p. 74-79.
Zhang, S., et al., Recent advances of the combination of Au/acid catalysis. Chinese Journal of Chemistry, 2014. 32(10): p. 937-956.
Padwa, A., Rhodium (II) mediated cyclizations of diazo alkynyl ketones. Journal of Organometallic Chemistry, 2000. 610(1-2): p. 88-101.
Akutagawa, S., Asymmetric synthesis by metal BINAP catalysts. Applied Catalysis A: General, 1995. 128(2): p. 171-207.
Kim, S.B., Catalysis Application of Metal (Rh, Ir) Quinonoid Complexes. Journal of Inorganic and Organometallic Polymers and Materials, 2014. 24(1): p. 58-65.
Suchorski, Y. and W. Drachsel, Catalytic reactions on platinum nanofacets: bridging the size and complexity gap. Topics in Catalysis, 2007. 46(1): p. 201-215.
Blaser, H.-U., et al., Enantioselective hydrogenation of α-ketoesters using cinchona modified platinum catalysts and related systems: a review. Catalysis today, 1997. 37(4): p. 441-463.
Lohray, B. and V. Bhushan, in Enantioselective Catalysis. Organic Synthesis Highlights III, 1998. 3: p. 44.
Rueping, M. and B.J. Nachtsheim, A review of new developments in the Friedel–Crafts alkylation–From green chemistry to asymmetric catalysis. Beilstein Journal of Organic Chemistry, 2010. 6(1): p. 6.
Torrent, M., et al., Density functional study of the [2+ 2]-and [2+ 3]-cycloaddition mechanisms for the osmium-catalyzed dihydroxylation of olefins. Organometallics, 1997. 16(1): p. 13-19.
Ishihara, A., et al., Tantalum oxide-based compounds as new non-noble cathodes for polymer electrolyte fuel cell. Electrochimica Acta, 2010. 55(26): p. 7581-7589.
Kidonakis, M. and M. Stratakis, Ligandless regioselective hydrosilylation of allenes catalyzed by gold nanoparticles. Organic letters, 2015. 17(18): p. 4538-4541.
Lantos, D., et al., Homogeneous gold-catalyzed hydrosilylation of aldehydes. Journal of organometallic chemistry, 2007. 692(9): p. 1799-1805.
Diez-Gonzalez, S. and S.P. Nolan, Copper, silver, and gold complexes in hydrosilylation reactions. Accounts of chemical research, 2008. 41(2): p. 349-358.
Nijamudheen, A. and A. Datta, Gold‐Catalyzed Cross‐Coupling Reactions: An Overview of Design Strategies, Mechanistic Studies, and Applications. Chemistry–A European Journal, 2020. 26(7): p. 1442-1487.
Liu, P. and J. Sun, Stereoselective Synthesis of Tetrasubstituted Furylalkenes via Gold-Catalyzed Cross-Coupling of Enynones with Diazo Compounds. Organic letters, 2017. 19(13): p. 3482-3485.
Garcia, P., et al., Gold-catalyzed cross-couplings: new opportunities for CC bond formation. ChemInform, 2010. 41(30): p. i.
Echavarren, A.M., A.S.K. Hashmi, and F.D. Toste, Gold catalysis–steadily increasing in importance. Advanced Synthesis & Catalysis, 2016. 358(9): p. 1347-1347.
Tomas-Mendivil, E., et al., Gold-Catalyzed Access to 1 H-Isochromenes: Reaction Development and Mechanistic Insight. ACS Catalysis, 2017. 7(1): p. 380-387.
Liang, S., et al., Commercial Supported Gold Nanoparticles Catalyzed Alkyne Hydroamination and Indole Synthesis. Advanced Synthesis & Catalysis, 2016. 358(20): p. 3313-3318.
Marinoiu, A., et al., Low-cost preparation method of well dispersed gold nanoparticles on reduced graphene oxide and electrocatalytic stability in PEM fuel cell. Arabian Journal of Chemistry, 2020. 13(1): p. 3585-3600.
Stegelmann, C., et al., Microkinetic modeling of ethylene oxidation over silver. Journal of Catalysis, 2004. 221(2): p. 630-649.
Goncharova, S., E. Paukshtis, and B. Bal'Zhinimaev, Size effects in ethylene oxidation on silver catalysts. Influence of support and Cs promoter. Applied Catalysis A: General, 1995. 126(1): p. 67-84.
Sawama, Y., et al., Disiloxane Synthesis Based on Silicon–Hydrogen Bond Activation using Gold and Platinum on Carbon in Water or Heavy Water. The Journal of Organic Chemistry, 2016. 81(10): p. 4190-4195.
Lyons, T.W. and M.S. Sanford, Palladium-catalyzed ligand-directed C− H functionalization reactions. Chemical reviews, 2010. 110(2): p. 1147-1169.
Littke, A.F. and G.C. Fu, Palladium‐catalyzed coupling reactions of aryl chlorides. Angewandte Chemie International Edition, 2002. 41(22): p. 4176-4211.
Blandez, J.F., et al., Palladium nanoparticles supported on graphene as catalysts for the dehydrogenative coupling of hydrosilanes and amines. Catalysis Science & Technology, 2015. 5(4): p. 2167-2173.
Blandez, J.F., et al., Nickel nanoparticles supported on graphene as catalysts for aldehyde hydrosilylation. Journal of Molecular Catalysis A: Chemical, 2016. 412: p. 13-19.
Biradar, A.V. and T. Asefa, Nanosized gold-catalyzed selective oxidation of alkyl-substituted benzenes and n-alkanes. Applied Catalysis A: General, 2012. 435: p. 19-26.
Marcano, D.C., et al., Improved synthesis of graphene oxide. ACS nano, 2010. 4(8): p. 4806-4814.
Zhang, Z., et al., Sodium citrate: A universal reducing agent for reduction/decoration of graphene oxide with au nanoparticles. Nano Research, 2011. 4(6): p. 599-611.
Chuang, M.-K., et al., Gold nanoparticle-decorated graphene oxides for plasmonic-enhanced polymer photovoltaic devices. Nanoscale, 2014. 6(3): p. 1573-1579.
Amir, M.N.I., et al., Tuning lattice strain in Quasi-2D Au-rGO nanohybrid catalysts for dimethylphenylsilane solid state silylation to disiloxane. Materials Science and Engineering: B, 2023. 291: p. 116395
Krishnamurthy, S., et al., Yucca-derived synthesis of gold nanomaterial and their catalytic potential. Nanoscale research letters, 2014. 9(1): p. 627.
García, C.P., et al., Microscopic analysis of the interaction of gold nanoparticles with cells of the innate immune system. Scientific Reports, 2013. 3(1): p. 1-7.
Shang, L., et al., Graphene‐supported ultrafine metal nanoparticles encapsulated by mesoporous silica: robust catalysts for oxidation and reduction reactions. Angewandte Chemie, 2014. 126(1): p. 254-258.
Emiru, T.F. and D.W. Ayele, Controlled synthesis, characterization and reduction of graphene oxide: A convenient method for large scale production. Egyptian Journal of Basic and Applied Sciences, 2017. 4(1): p. 74-79.
Amanulla, B., et al., Selective colorimetric detection of nitrite in water using chitosan stabilized gold nanoparticles decorated reduced graphene oxide. Scientific Reports, 2017. 7(1): p. 1-9.
Tran, T.D., et al., Gold nanoparticles as an outstanding catalyst for the hydrogen evolution reaction. Chemical Communications, 2018. 54(27): p. 3363-3366.
Mohan, J.C., et al., Functionalised gold nanoparticles for selective induction of in vitro apoptosis among human cancer cell lines. Journal of experimental nanoscience, 2013. 8(1): p. 32-4
Tanaka, K. and F. Toda, Solvent-Free Organic Reactions. Chem. Rev, 2000. 100: p. 1025-1074.
Loupy, A., Solvent-free reactions, in Modern Solvents in Organic Synthesis. 1999, Springer. p. 153-207.
Downloads
Published
Issue
Section
License
