Abstract
This paper describes the preparation, broad characterization and study of activity in hydrogenation and hydroformylation reactions of an easily produced 0.18% Rh/Al2O3. Analytical studies on fresh and recycled samples shed light on the smart properties of such catalyst. Results showed high activity as well as fine/excellent chemoselectivity or regioselectivity, characteristics that may suggest a wide range of applicability.
Graphic Abstract
The low metal content catalyst 0.18% Rh/Al2O3 was very active in both hydrogenation and hydroformylation reactions so providing intermediates for valuable APIs, as Nabumetone and Eletriptan, and a fragrance with a fresh, green-floral smell, that recalls scent of lily of the valley.
Similar content being viewed by others
References
Blaser HU (2000) Catal Today 60:161
Bartolomew CH, Farrauto RJ (2006) Fundamentals of Industrial Catalytic Processes, 2nd edn. Wiley, Hoboken
Varga E, Pusztai P, Oszkó A, Baán K, Erdőhelyi A, Kónya Z, Kiss J (2016) Langmuir 32:2761–2770
Song T, Ma Z, Yang Y (2019) ChemCatChem 11:1313
Mendes-Burak J, Ghaffari B, Copéret C (2019) ChemCommun 55:179–181
Louis C, Delannoy L (2019) AdvCatal 64:1
Reddy SK, Enumula SS, Koppadi KS, Kamaraju SRR, Burri DR (2020) MolCatal 482:110686
Zhang L, Zhou M, Wang A, Zhang T (2020) Chem Rev 120:683
Cavuoto D, Zaccheria F, Marelli M, Evangelisti C, Piccolo O, Ravasio N (2020) Catalysts 10:515
Campelo JM, Garcia A, Luna D, Marinas JM (1984) React KinetCatalLett 26:73
Yamaguchi M, Nitta A, Reddy RS, Hirama M (1999) Synlett 117
Fagassy G, Hegedus L, Tungler A, Lévai A, Màthé T (2000) J MolCatal 154:237
Dell’Anna MM, Gallo V, Mastrorilli P, Romanazzi G (2010) Molecules 15:3311
Piccolo O, Verrazzani A (2006) US 7087548 (Chemi SpA)
Amsler J, Sarma BB, Agostini G, Prieto G, Plessow PN, Studt F (2020) J Am ChemSoc 142:5087
Lenarda M, Ganzerla R, Paganelli S, Storaro L, Zanoni R (1996) J MolCatal A: Chem 105:117
Dharmidhikari S, Abraham MA (2000) J Supercrit Fluids 18:1
Jagtap SA, Bhosale MA, Sasaki T, Bhanage BM (2016) Polyhedron 120:162
Armarego WLF (2017) Purification of laboratory chemicals, 8th edn. Elsevier, Oxford
Rathod VD, Paganelli S, Piccolo O (2016) CatalCommun 84:52
Bumagin NA, Kasatkin AN, Beletskaya IP (1984) SeriyaKhimicheskaya 8:1858
Souza Santos P, Souza Santos H, Toledo SP (2000) Mat Res 3:104–114
Rozita Y, Brydson R, Scott AJ (2009) J Phys 241:12096
Peri JB (1965) J PhysChem 69:231
Tsyganenko AA, Pozdnyakov DV, Filimonov VN (1975) J MolStruct 29:299
Basile F, Bersani I, Del Gallo P, Fiorilli S, Fornasari G, Gary D, Mortera R, Onida B, Vaccari A (2011) Int J Spectr Hindawi, Article ID 458089.
Yates C (1979) J ChemPhys 71:3908
Solymosi F (1985) Pásztor M 89:4789–4793
Bergeret G, Gallezot P, Gelin P, Taarit BY, Lefebvre F, Naccache C, Shannon RD (1987) J Catal 104:279–287
Kukovecz Á, Pótári G, Oszkó A, Kónya Z, Erdőhelyi A, Kiss J (2011) Surf Sci 605:1048–1055
Kukovecz Á, Kordás K, Kiss J, Kónya Z (2016) Surf Sci Rep 71:473–546
Hedne T, Samulesson O, Währborg P, Wadenvik H, Ung KA, Ekbom A (2004) Drugs 64:2315
Newport Premium Dabase; https://clarivate.com/tag/newport-premium/
Gaster LM (1980) US 4221741, (Beecham Group Ltd)
Ramachandran V, Belmont S (1998) US 5847225, (Albemarle Corp.)
Ravasio N, Zaccheria F, Allegrini P, Ercoli M (2007) Catal Today 121:2
Evangelisti C, Panziera N, Vitulli M, Pertici P, Balzano F, Uccello-Barretta G, Salvadori P (2008) ApplCatal A Gen 339:84
Viviano M, Glasnov TN, Reichart B, Tekautz G, Kappe CO (2011) Org Process Res Dev 15:858
Macor JE, Wythes JM (1996) US 5545644, (Pfizer Inc.)
R J (2007) US 7288662, (Pfizer Inc.)
Serafini S, Castellin A, Dal Santo C (2013) US 8426612, (F.I.S. SpA)
Rao SV, Shrikant HH, Kumar BS, Krishna GS (2017) Asian J Chem 29:2232
Potluri RB, Kodali HP, Venturi SR, Tadimalla VS (2011) WO2011024039
Pullagurla MR, Rangisetty JB, Naidu N, Maddela N, Nagarapu R, Polagani PR (2014) US 8633239.
Ranu BC, Guchhait SK, Ghosh K (1998) J Org Chem 63:5250
Laxminarayana K, Rajendiran C, Mukkanti K (2013) Asian J Chem 25:1661
Kusumba VG, Sankineni SK, Neela PK, Pradhan NS, Valgeirsson J (2010) US 2010285075 (Actavis Group)
Tassini R, La Sorella G, Montin D, Paganelli S, Baldi F, Piccolo O (2012) Chimica e Industria 94:157
Paganelli S, Piccolo O, Rathod VD (2016) XIX Congresso Nazionale di Catalisi GIC, Padova
Cornils B, Börner A, Franke R, Zhang B, Wiebus E, Schmid K (2018) In: Cornils B, Hermann WA, Beller M, Paciello R (eds) Applied homogeneous catalysis with organometallic compounds. Wiley, Weinheim
Acknowledgements
Role of the authors. OP and SP: conceptualization, supervision, writing-original draft preparation, writing-reviewing and editing; RT and VDR investigation; BO and SF some methodology for the characterization of the catalyst. All authors approved final manuscript. The authors are also grateful to Dr. Laura Sperni (Ca' Foscari University of Venice) for GC–MS analyses.
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Conflict of interest
The authors declare no conflict of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Paganelli, S., Tassini, R., Rathod, V.D. et al. A Low Rhodium Content Smart Catalyst for Hydrogenation and Hydroformylation Reactions. Catal Lett 151, 1508–1521 (2021). https://doi.org/10.1007/s10562-020-03407-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-020-03407-5