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Gas-phase Beckmann rearrangement of cyclododecanone oxime on Al,B-MCM-41 mesoporous materials

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Abstract

Gas-phase Beckmann rearrangement of cyclododecanone oxime (Cdox) to ω-laurolactam is reported for the first time on Al,B-MCM-41 catalysts. The Cdox conversion was studied by using a temperature programmed reaction experiment in the 325–450 °C temperature range employing 0.15 M Cdox in toluene/acetone solution. The oxime conversion increased gradually with reaction temperature from ca. 90% at 325 °C to ca. 95% at 450 °C, whereas the yield of the desired product ω-laurolactam decreased. The optimal reaction temperature was 375 °C, which balanced the conversion of Cdox, selectivity to ω-laurolactam and catalyst lifetime. In parallel, liquid-phase experiments were carried out under conventional heating. Weak and medium strength acid sites, higher strong acid B/L ratios and adequate pore diameter of untreated Al,B-MCM-41 materials favored an optimal performance for the gas-phase Beckmann rearrangement of Cdox, clearly improving the conversion, selectivity to ω-laurolactam and catalyst lifetime in gas-phase with respect to the conventional liquid-phase reactions.

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Acknowledgements

This research was subsidized by Grants from the Dirección General de Investigación (Projects CTQ2007-65754/PPQ, CTQ2008-01330), Ministerio de Ciencia y Tecnología, FEDER funds, and from the Consejería de Innovación, Ciencia y Empresa (Junta de Andalucía, Project P07-FQM-2695).

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Authors and Affiliations

  1. Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Córdoba, Campus Universitario de Rabanales, Edificio Marie Curie (C3), 14014, Córdoba, Spain

    Tomas David Conesa, Rafael Luque, Juan Manuel Campelo, Diego Luna, Jose Maria Marinas & Antonio Angel Romero

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  1. Tomas David Conesa
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  2. Rafael Luque
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  3. Juan Manuel Campelo
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  4. Diego Luna
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  5. Jose Maria Marinas
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  6. Antonio Angel Romero
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Correspondence to Antonio Angel Romero.

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Conesa, T.D., Luque, R., Campelo, J.M. et al. Gas-phase Beckmann rearrangement of cyclododecanone oxime on Al,B-MCM-41 mesoporous materials. J Mater Sci 44, 6741–6746 (2009). https://doi.org/10.1007/s10853-009-3601-x

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