A recyclable nanoparticle-supported rhodium catalyst for hydrogenation reactions

Molecules

Volumn 15, Issue 5, 2010, Pages 3311-3318

  Dell'Anna, Maria Michela ^a   Gallo, Vito ^a   Mastrorilli, Piero ^a   Romanazzi, Giuseppe ^a  

^a POLITECNICO DI BARI   (Italy)

Author keywords

Halonitroanilines; Hydrogenation; Nitroaromatics; Supported rhodium complex

Indexed keywords

ALDEHYDE; ALKENE; ANILINE; ANILINE DERIVATIVE; KETONE; NANOPARTICLE; NITRILE; RHODIUM;

ARTICLE; CATALYSIS; CHEMISTRY; HYDROGENATION; SYNTHESIS;

ALDEHYDES; ALKENES; ANILINE COMPOUNDS; CATALYSIS; HYDROGENATION; KETONES; NANOPARTICLES; NITRILES; RHODIUM;

EID: 77952860138     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15053311     Document Type: Article

References (31)

1. McNamara, C.A.; Dixon, M.J.; Bradley, M. Recoverable catalysts and reagents using recyclable polystyrene-based supports. Chem. Rev. 2002, 102, 3275-3300.
2. McMorn, P.; Hutchings, G.J.; Heterogeneous enantioselective catalysts: Strategies for the immobilisation of homogeneous catalysts. Chem. Soc. Rev. 2004, 33, 108-122.
3. Mastrorilli, P.; Nobile, C.F. Supported catalysis from polymerisable transition metal complexes. Coord. Chem. Rev. 2004, 248, 377-395.
4. Mastrorilli, P.; Nobile, C.F. Catalytic activity of macromolecules obtained from metal-containing monomers. In Metal-coordination polymers; Abd-El-Aziz, A.S., Carraher, C.E., Pittman, C.U., Zelding, M., Eds.; John Wiley & Sons: Hoboken, NJ, USA, 2005; pp. 227-257.
5. Heitbaum, M.; Glorius, F.; Escher, I. Asymmetric Heterogeneous Catalysis. Angew. Chem. Int. Ed. 2006, 45, 4732-4762.
6. Corma, A.; Garcia, H. Silica-Bound Homogenous Catalysts as Recoverable and Reusable Catalysts in Organic Synthesis. Adv. Synth. Catal. 2006, 348, 1391-1412.
7. Yang, H.; Han, X.; Ma, Z.; Wang, R.; Liu, J.; Ji, X. Palladium-guanidine complex immobilized on SBA-16: A highly active and recyclable catalyst for Suzuki coupling and alcohol oxidation. Green Chem. 2010, 12, 441-451.
8. Egbebi, A.; Schwartz, V.; Overbury, S.H.; Spivey, J.J. Effect of Li Promoter on titania-supported Rh catalyst for ethanol formation from CO hydrogenation. Catal. Today 2010, 149, 91-97.
9. Swennenhuis, B.H.G.; Chen, R.; van Leeuwen, P.W.N.M.; de Vries, J.G.; Kamer, P.C.J. Supported Chiral Monodentate Ligands in Rhodium-Catalysed Asymmetric Hydrogenation and Palladium-Catalysed Asymmetric Allylic Alkylation. Eur. J. Org. Chem. 2009, 5796-5803.
10. Motoyama, Y.; Takasaki, M.; Yoon, S.-H.; Mochida, I.; Nagashima, H. Rhodium Nanoparticles Supported on Carbon Nanofibers as an Arene Hydrogenation Catalyst Highly Tolerant to a Coexisting Epoxido Group. Org. Lett. 2009, 11, 5042-5045.
11. Miyake, T.; Makino, T.; Taniguchi, S.; Watanuki, H.; Niki, T.; Shimizu, S.; Kojima, Y.; Sano, M. Alcohol synthesis by hydrogenation of fatty acid methyl esters on supported Ru-Sn and Rh-Sn catalysts. Appl. Catal. A Gen. 2009, 364, 108-112.
12. Travis, A.S. Anilines: Historical Background. In The Chemistry of Anilines; Rappoport, Z., Ed.; John Wiley & Sons: Chichester, UK, 2007; pp. 1-75.
13. Okazaki, Y.; Yamashita, K.; Ishii, H.; Sudo, M.; Tsuchitani, M. Potential of neurotoxicity after a single oral dose of 4-bromo-, 4-chloro-, 4-fluoro- or 4-iodoaniline in rats. J. Appl. Toxicol. 2003, 23, 315-322.
14. Rylander, P.N. Hydrogenation Methods; Academic Press: New York, NY, USA, 1995; pp. 105-116.
15. Baltzly, R.; Phillips, A.P. The catalytic hydrogenolysis of halogen compounds. J. Am. Chem. Soc. 1946, 68, 261-265.
16. Yang, X.; Liu, H.; Zhong, H. Hydrogenation of o-chloronitrobenzene over polymer-stabilized palladium-platinum bimetallic colloidal clusters. J. Mol. Catal. A Chem. 1999, 147, 55-62.
17. Xu, S.; He, J.; Cao, S. Catalytic behaviors of the palladium complex of MgO-supported melamino-formaldehyde polymer for hydrogenations of different substrates. J. Mol. Catal. A Chem. 1999, 147, 155-158.
18. Sreedhar, B.; Surendra Reddy, P.; Keerthi Devi, D. Direct one-pot reductive amination of aldehydes with nitroarenes in a domino fashion: Catalysis by gum-acacia-stabilized palladium nanoparticles. J. Org. Chem. 2009, 74, 8806-8809.
19. Yang, X.; Deng, Z.; Liu, H. Modification of metal complex on hydrogenation of o-chloronitrobenzene over polymer-stabilized platinum colloidal clusters. J. Mol. Catal. A Chem. 1999, 144, 123-127.
20. Khilnani, V.L.; Chandalia, S.B. Selective hydrogenation. I. para-chloronitrobenzene to para- chloroaniline platinum on carbon as catalyst. Org. Process Res. Dev. 2001, 5, 257-262.
21. 3. J. Mol. Catal. A Chem. 2007, 273, 160-168.
22. Liang, M.; Wang, X.; Liu, H.; Liu, H.; Wang, Y. Excellent catalytic properties over nanocomposite catalysts for selective hydrogenation of halonitrobenzenes. J. Catal. 2008, 255, 335-342.
23. Motoyama, Y.; Kamo, K.; Nagashima, H.; Catalysis in polysiloxane gels: Platinum-catalyzed hydrosilylation of polymethylhydrosiloxane leading to reusable catalysts for reduction of nitroarenes. Org. Lett. 2009, 11, 1345-1348.
24. Yuan, X.; Yan, N.; Xiao, C.; Li, C.; Fei, Z.; Cai, Z.; Kou, Y.; Dyson, P.J. Highly selective hydrogenation of aromatic chloronitro compounds to aromatic chloroamines with ionic-liquid-like copolymer stabilized platinum nanocatalysts in ionic liquids. Green Chem. 2010, 12, 228-233.
25. Liu, M.; Yu, W.; Liu, H. Selective hydrogenation of o-chloronitrobenzene over polymer-stabilized ruthenium colloidal catalysts. J. Mol. Catal. A Chem. 1999, 138, 295-303.
26. Zuo, B.J.; Wang, Y.; Wang, L.; Zhang, J.L.; Wu, N.Z.; Peng, L.D.; Gui, L.L.; Wang, X.D.; Wang, R.M.; Yu, D.P. An efficient ruthenium catalyst for selective hydrogenation of ortho- chloronitrobenzene prepared via assembling ruthenium and tin oxide nanoparticles. J. Catal. 2004, 222, 493-498.
27. Basu, B.; Das, P.; Das, S. Transfer hydrogenation using recyclable polymer-supported formate (PSF): Efficient and chemoselective reduction of nitroarenes. Mol. Divers. 2005, 9, 259-262; and references therein.
28. Chaubal, N.S.; Sawant, M.R. Nitro compounds reduction via hydride transfer using mesoporous mixed oxide catalyst. J. Mol. Catal. A Chem. 2007, 261, 232-241; and references therein.
29. Zhou, L.; Gu, H.; Yan, X. A novel transfer hydrogenation with high hydrogen utilization for the hydrogenation of halogenated nitrobenzene without hydrodehalogenation. Catal. Lett. 2009, 132, 16-21.
30. Dell'Anna, M.M.; Mastrorilli, P.; Rizzuti, A.; Suranna, G.P.; Nobile, C.F. Synthesis and copolymerization of rhodium(I) and palladium(II) complexes with the deprotonated form of 2- (acetoacetoxy)ethyl methacrylate. Inorg. Chim. Acta 2000, 304, 21-25.
31. Mastrorilli, P.; Nobile, C.F.; Suranna, G.P.; Corradi, A.; Leonelli, C.; Veronesi, P. Morphological characterization of poly(phenylacetylene) nanospheres prepared by homogeneous and heterogeneous catalysis. Appl. Organomet. Chem. 2003, 17, 711-716.