Abstract
The use of mononuclear Cu(II) 2,2′-bipyridine and 1,10-phenantroline complexes as catalysts in the oxidation of benzene, using hydrogen peroxide and tert-butyl hydroperoxide as oxidant in CH3CN/H2O solution is presented. The reactions were carried out at 25 and at 50 °C. The complexes [Cu(bipy)3]Cl2 · 6H2O (1), [Cu(bipy)2Cl]Cl · 5H2O (2), [Cu(bipy)Cl2] (3), [Cu(phen)3]Cl2 · 7H2O (4), [Cu(phen)2Cl]Cl · 5H2O (5), [Cu(phen)Cl2] (6) were able to oxidize benzene into phenol, hydroquinone and p-benzoquinone. Highest conversion (22%) was obtained using [Cu(Phen)Cl2] (6) as catalyst.
Similar content being viewed by others
References
Gomes MFT, Antunes OAC (1996) Catal Lett 38:133
Gomes MFT, Antunes OAC (1996) Catal Lett 42:213
Lima LF, Corraza ML, Cardozo-Filho L, Alvarez HM, Antunes OAC (2006) Braz J Chem Eng 23:83
Lima LF, Cardozo-Filho L, Arroyo PA, Alvarez HM, Antunes OAC (2005) Kinet Catal Lett 84:69
Silva AD, Patitucci ML, Bizzo HR, D’Elia E, Antunes OAC (2002) Catal Commun 3:435
Salomão GC, Olsen MHN, Drago V, Fernandes C, Cardozo Filho L, Antunes OAC (2007) Catal Commun 8:69
Olsen MNH, Salomão GC, Drago V, Fernandes C, Horn A Jr, Cardozo Filho L, Antunes OAC (2005) J Supercrit Fluids 34:119
Silva GC, Parrilha GL, Carvalho NMF, Drago V, Fernandes C, Horn A Jr, Antunes OAC (2008) Catal Today 133–135:684
Carvalho NMF, Horn A Jr, Antunes OAC (2006) Appl Catal A 305:140
Canhota FP, Salomão GC, Carvalho NMF, Antunes OAC (2007) Catal Commun 9:182
Silva AC, Fernández TL, Carvalho NMF, Herbst MH, Bordinhão J, Horn A Jr, Wardell JL, Oestreicher EG, Antunes OAC (2007) Appl Catal A 317:154
Schimidt RJ (2005) Appl Catal A 280:89
Lücke B, Narayana KV, Martin A, Jähnisch K (2004) Adv Synth Catal 346:1407
Shilov AE, Shul’pin GB (1997) Chem Rev 97:2879
Punniyamurthy T, Velusamy S, Iqbal J (2005) Chem Rev 105:2329
Parida KM, Dash SS (2007) J Coll Interface Sci 316:541
Liu Y, Murata K, Inaba M (2005) Catal Commun 6:679
Esmelindro MC, Oestreicher EG, Caovilla M, Lessa JA, Fernandes C, Dariva C, Egues SM, Bortoluzzi AJ, Antunes OAC (2006) J Braz Chem Soc 17:1551
Jolley RL, Evans LH, Makino N, Mason HS (1974) J Biol Chem 249:335
Chan SI, Yu SS-F (2008) Acc Chem Res 41:969
Sotomayor MDP, Tanaka AA, Kubota LT (2003) Electrochim Acta 48:855
Stephens FS, Tucker PA (1973) J Chem Soc Dalton Trans 2293
Hérnandez-Molina M, González-Platas J, Ruiz-Pérez C, Lloret F, Julve M (1999) Inorg Chim Acta 284:258
Garlan MT, Grandjean D, Spodine E, Atria AM, Manssur J (1988) Acta Crystallogr Sect C Cryst Struct Commun 44:1209
Jian FF, Lin JH, Zhang SS (2001) Chin J Chem 19:772
Murphy G, O’Sullivan C, Murphy B, Hathaway B (1998) Inorg Chem 37:240
Faye GH (1966) Can J Chem 44:2165
Quintanilla A, Casas JA, Mohedano AF, Rodríguez JJ (2006) Appl Catal B 67:206
Duprez D, Delanoë F, Barbier J Jr, Isnard P, Blanchard G (1996) Catal Today 29:317
Alejandre A, Medina F, Fortuny A, Salagre P, Sueiras JE (1998) Appl Catal B 16:53
Olsen MNH, Salomão GC, Fernandes C, Drago V, Horn A Jr, Cardozo-Filho L, Antunes OAC (2007) Acta Scientiarum Technol 29:43
Acknowledgments
Financial support from CNPq, CAPES, FAPERJ and FINEP are gratefully acknowledged.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Detoni, C., Carvalho, N.M.F., de Souza, R.O.M.A. et al. Oxidation of Benzene Catalyzed by 2,2′-Bipyridine and 1,10-Phenantroline Cu(II) Complexes. Catal Lett 129, 79–84 (2009). https://doi.org/10.1007/s10562-008-9830-9
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-008-9830-9