Highly selective n-alkanes oxidation to ketones with molecular oxygen catalyzed by SBA-15 supported rhenium catalysts

Gopal S. Mishra; Kelly Machado; Anil Kumar

Journal of Industrial and Engineering Chemistry, Vol.20, No.4, 2228-2235, July, 2014

DOI10.1016/j.jiec.2013.09.055 Export Citation

Highly selective n-alkanes oxidation to ketones with molecular oxygen catalyzed by SBA-15 supported rhenium catalysts

Gopal S. Mishra^†, Kelly Machado, and Anil Kumar¹

Department of Chemistry, University of Tras-os-Montes and Alto Douro (UTAD), Vila Real 5001801, Portugal
¹Department of Chemical Engineering, Indian Institute of Technology (IITK), Kanpur 208016, India

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A series of tricarbonyl Re(V) complexes, i.e. [Re(CO)3(k3-PN2)] (1), [Re(CO)3Br(k2-H2PNO)] (2), and [Re(CO)3Br(k2-HPN-Pip)] (3), have been covalently anchored over modified SBA-15 as supported catalysts. Remarkably, high catalytic turnover numbers from 2240 to 2857 with high ketone selectivity was obtained for both C5 and C6-alkanes. Best oxidation condition was optimized by the variation of temperature, pressure, time and catalyst amount. A thermal stability test indicates that the catalysts are stable up to 200 ℃ and ICP shows negligible metal loss from the catalyst surface, after the 7th catalytic cycle, allowing further use.

Keywords:Re catalyst;Heterogeneous catalysis;Alkanes;Oxygen;Selectivity

[References]

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de Vos DE, Sels BF, Jacobs PA, Adv. Catal., 46, 1 (2001)
Mishra GS, Kumar A, Tavares PB, J. Mol. Catal. A-Chem., 357, 125 (2012)
Mishra GS, Kumar A, Catal. Sci. Technol., 1, 1224 (2011)
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Correia JDG, Domingos A, Santos I, Eur. J. Inorg. Chem., 7, 1523 (2000)
Correia JDG, Domingos A, Santos I, Spies H, J. Chem. Soc. Dalton Trans., 15, 2245 (2001)
Mishra GS, Kumar A, Appl. Catal. A: Gen., 1, 429 (2012)
Mishra GS, Alegria ECB, Martins LR, Pombeiro AJL, Appl. Catal. A: Gen., 285, 92 (2008)
Lin SS, Weng HS, Appl. Catal. A: Gen., 118(1), 21 (1994)
Pires EL, Magalhaes JC, Schuchardt U, Appl. Catal. A: Gen., 203(2), 231 (2000)
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Silva TFS, Mishra GS, da Silva MFG, Wanke R, Martins LMDRS, Pombeiro AJL, Dalton Trans., 42, 9207 (2009)
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Genti G, Lopez JM, Iapalucci C, Appl. Catal. A: Gen., 46, 167 (1989)
Thomas JM, Raja R, Shanker G, Robert GB, Nature, 398, 227 (1999)
O'Connor RP, Schmidt LD, Chem. Eng. Sci., 55(23), 5693 (2000)
Correia JDG, Domingos A, Domingos A, Poula A, Santos I, Dalton Trans., 2477 (2000)
Zhao DY, Feng JL, Huo QS, Melosh N, Fredrickson GH, Chmelka BF, Stucky GD, Science, 279(5350), 548 (1998)
Kumar D, Landry CC, Microporous Mesoporous Mater., 98, 309 (2007)
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Mishra GS, Sinha S, Catal. Lett., 125(1-2), 139 (2008)
Pohorecki R, Baldyga J, Moniuk W, Podgorska W, Zdrojkowski A, Wierzchowski PT, Chem. Eng. Sci., 56(4), 1285 (2001)
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[1] Hodnett BK, Heterogeneous Catalytic Oxidation: Fundamental and Technological Aspects of the Selective and Total Oxidation of Organic Compounds, John Wiley & Sons, New York, 2000.

[2] Cole-Hamilton DJ, Science, 299, 1702 (2003)

[3] Centi G, Cavani F, Trifiro F, Selective Oxidation by Heterogeneous Catalysis, Kluwer Academic/Plenum Publishers, New York, 2001.

[4] Fan J, Gao Y, J. Exp. Nanosci., 1, 457 (2006)

[5] de Vos DE, Sels BF, Jacobs PA, Adv. Catal., 46, 1 (2001)

[6] Mishra GS, Kumar A, Tavares PB, J. Mol. Catal. A-Chem., 357, 125 (2012)

[7] Mishra GS, Kumar A, Catal. Sci. Technol., 1, 1224 (2011)

[8] Mishra GS, Silva TFS, Martins LMDRS, Pombeiro AJL, Pure Appl. Chem., 81, 1217 (2009)

[9] Correia JDG, Domingos A, Santos I, Eur. J. Inorg. Chem., 7, 1523 (2000)

[10] Correia JDG, Domingos A, Santos I, Spies H, J. Chem. Soc. Dalton Trans., 15, 2245 (2001)

[11] Mishra GS, Kumar A, Appl. Catal. A: Gen., 1, 429 (2012)

[12] Mishra GS, Alegria ECB, Martins LR, Pombeiro AJL, Appl. Catal. A: Gen., 285, 92 (2008)

[13] Lin SS, Weng HS, Appl. Catal. A: Gen., 118(1), 21 (1994)

[14] Pires EL, Magalhaes JC, Schuchardt U, Appl. Catal. A: Gen., 203(2), 231 (2000)

[15] Queeney KT, Chen DA, Friend CM, J. Am. Chem. Soc., 119(29), 6945 (1997)

[16] Silva TFS, Mishra GS, da Silva MFG, Wanke R, Martins LMDRS, Pombeiro AJL, Dalton Trans., 42, 9207 (2009)

[17] Arakawa H, Aresta M, Armor JN, Barteau MA, Beckman EJ, Bell AT, Bercaw E, Creutz C, Dinjus E, Dixon DA, Domen K, DuBois DL, Eckert J, Fujita E, Gibson DH, Goddard WA, Goodman DW, Keller J, Kubas GJ, Kung HH, Lyons JE, Manzer LE, Marks TJ, Morokuma K, Nich, Chem. Rev., 101(4), 953 (2001)

[18] Olah GA, Molnar A, Hydrocarbon Chemistry, 3rd ed., Wiley, New York, 2003p. 1.

[19] Zazhigalov VA, Haber J, Stoch J, Cheburakova EV, Catal. Commun., 2, 375 (2001)

[20] Sookraj SH, Engelbrecht D, Catal. Today, 49(1-3), 161 (1999)

[21] Genti G, Lopez JM, Iapalucci C, Appl. Catal. A: Gen., 46, 167 (1989)

[22] Thomas JM, Raja R, Shanker G, Robert GB, Nature, 398, 227 (1999)

[23] O'Connor RP, Schmidt LD, Chem. Eng. Sci., 55(23), 5693 (2000)

[24] Correia JDG, Domingos A, Domingos A, Poula A, Santos I, Dalton Trans., 2477 (2000)

[25] Zhao DY, Feng JL, Huo QS, Melosh N, Fredrickson GH, Chmelka BF, Stucky GD, Science, 279(5350), 548 (1998)

[26] Kumar D, Landry CC, Microporous Mesoporous Mater., 98, 309 (2007)

[27] Vennat M, Herson P, Bregeault JM, Shul’pin GB, Eur. J. Inorg. Chem., 5, 908 (2003)

[28] Shul’pin GB, C. R. Chim. 6 (2003) 163.

[29] Hartman M, Ernst S, Angew. Chem.-Int. Edit., 39, 888 (2000)

[30] Kumar A, Mishra GS, Kumar A, Trans. Met. Chem., 28, 913 (2003)

[31] Tolman CA, Druliner JD, Nappa MJ, Herron N, in: Hill CL (Ed.), Activation and Functionalization of Alkanes, Wiley, New York, 1989, p. 303.

[32] Mishra GS, Sinha S, Catal. Lett., 125(1-2), 139 (2008)

[33] Pohorecki R, Baldyga J, Moniuk W, Podgorska W, Zdrojkowski A, Wierzchowski PT, Chem. Eng. Sci., 56(4), 1285 (2001)

[34] Zhan BZ, Moden B, Dakka J, Santiesteban JG, Iglesia E, J. Catal., 245(2), 316 (2007)