Abstract
Homogenous cyclohexanone oxidation was catalyzed by a series of Keggin-type polyoxometalates as formula H3PMo12O40, Cs3PMo12O40, CsSnPMo12O40, Cs2Sn0.5PMo12O40 and HSnPMo12O40 using hydrogen peroxide H2O2 (30%), without solvent. The following reaction products, adipic, glutaric and succinic acids, butane-1,3-diol and ε-caprolactone were identified and quantified by high-performance liquid chromatography (HPLC). The catalysts were prepared and characterized by Fourier transform infrared spectroscopy (FTIR), chemical analysis (ICP), 31P and 133Cs nuclear magnetic resonance spectroscopies and in situ FTIR of pyridine adsorption. The presence of both BrØnsted and Lewis acid sites was evidenced for CsSnPMo12O40, Cs2Sn0.5PMo12O40 and HSnPMo12O40. Among them, HSnPMo12O40 exhibited total conversion with adipic acid, as major product (60% of yield).
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References
Krow GR (2004) Org React 43:251–798
Sager WF, Duckworth A (1955) J Am Chem Soc 77(1):188–190
Pillai UR, Sahle-Demessie E (2003) J Mol Catal A Chem 191(1):93–100
Corma A, Navarro MT, Nemeth L, Renz M (2001) Chem Commun 21:2190–2191
Corma A, Navarro MT, Renz M (2003) Chem Commun 219:242–246
Bhanja P, Chatterjee S, Patra AK, Bhaumik A (2018) J Colloid Interface Sci 511:92–100
Lambert A, Macquarrie DJ, Carr G, Clark JH (2000) New J Chem 24:485–488
Chen C, Peng J, Li B, Wang L (2009) Catal Lett 131(3–4):618
Nomiya K, Miwa M, Sugaya Y (1984) Polyhedron 3(5):607–610
Cavani F, Ferroni L, Frattini A, Lucarelli C, Mazzini A, Raabova K, Alini S, Accorinti P, Babini P (2011) Appl Catal A 391(1):118–124
Idrissou Y, Mouanni S, Amitouche D, Mazari T, Catherine Roch-Marchal C, Rabia C (2018) Bull Chem React Eng Catal 13(2):386–391
Tahar A, Benadji S, Mazari T, Dermeche L, Marchal-Roch C, Rabia C (2015) Catal Lett 145(2):569–575
Mazari T, Benadji S, Tahar A, Dermeche L, Rabia C (2013) J Mater Sci Eng B 3(3):146–215
Benadji S, Mazari T, Dermeche L, Salhi N, Cadot E, Rabia C (2013) Catal Lett 143(8):749–755
Mouanni S, Mazari T, Amitouche D, Benadji S, Dermeche L, Catherine Roch-Marchal C, Rabia C (2019) Compt Rendu Chim 22(4):327–336
Mouanni S, Mazari T, Amitouche D, Benadji S, Dermeche L, Catherine Roch-Marchal C, Rabia C (2018) Bull Chem React Eng Catal 13(2):386–391
Mouheb L, Dermeche L, Mazari T, Benadji S, Essayem N, Rabia C (2018) Catal Lett 148(2):612–620
Moudjahed M, Dermeche L, Benadji S, Mazari T, Rabia C (2016) J Mol Catal A Chem 414:72–77
Guerroudj RM, Dermeche L, Mouheb L, Mazari T, Amitouche D, Benadji S, Rabia C (2019) Bull Chem React Eng Catal 14(2):283–293
Renz M, Blasco T, Corma A, Fornés V, Jensen R, Nemeth L (2002) Chemistry 8(20):4708–4717
Tsigdinos GA (1974) Ind Eng Chem Prod Res Dev 13:267–274
Rocchicioli-Deltcheff C, Thouvenot R, Franck R (1976) Spectrochim Acta A 32:587–597
Cavani F, Mezzogori R, Pigamo A, Trifiro F (2001) Chem Eng J 82(1–3):33–42
Jacobs PA (1984) Characterization of heterogeneous catalysts. Marcel Dekker, New York
Parry EP (1963) J Catal 2(5):371–379
Yashima T, Hara N (1972) J Catal 27(2):329–333
Furuta M, Sakata K, Misono M, Yoneda Y (1979) Chem Lett 8(1):31–34
Emeis CA (1993) J Catal 141(2):347–354
Amitouche D, Haouas M, Mazari T, Mouanni S, Canioni R, Rabia C, Marchal-Roch C (2018) Appl Catal A 561:104–116
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Mouheb, L., Dermeche, L., Essayem, N. et al. Keggin-Type Mixed Polyoxomolybdates Catalyzed Cyclohexanone Oxidation by Hydrogen Peroxide: In Situ IR Pyridine Adsorption. Catal Lett 150, 3327–3334 (2020). https://doi.org/10.1007/s10562-020-03231-x
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DOI: https://doi.org/10.1007/s10562-020-03231-x