Aqueous-biphasic hydroformylation of 1-hexene catalyzed by the complex HCo(CO)[P(o-C6H4SO3Na)]3

María Modroño-Alonso, William Castro, Francisco Lopez-Linares, Merlín Rosales, Pablo Jose Baricelli

Abstract


The water soluble cobalt complex HCo(CO)[P(o-C6H4SO-3Na)]3 was used as catalyst precursor for the biphasic aqueous hydroformylation of 1-hexene. The complex was synthesized by reductive carbonylation of CoCl2.6H2O in the presence of o-TPPTS ([P(o-C6H4SO3Na)]3) under nitrogen atmosphere and characterized by FTIR, 1H NMR and 31P {1H} NMR, 13C NMR, DEPT – 135, COSY, HSQC, MS (ESI). The catalytic activity of the complex in the biphasic hydroformylation reaction of 1-hexene was evaluated under moderate reaction conditions. The pressure and temperature were varied from 4137 – 7584 kPa (600-1100 psi) of syngas and from 353 – 383 K (80 – 110 °C), respectively. The 1-hexene concentration was varied from 0.021-0,11M and the catalyst from 4x10-4 - 1.1x10-3 M. The best conversion at 363 K and 7584 kPa and 7.5 h was 62% with selectivity towards aldehydes (heptanal and 2-methyl-hexanal) of 66% to with l/b ratio of 2.6. The recycling of the catalytic precursor after four successive times, did not show any loss on the activity, having selectivity towards aldehyde up to 60%.

Keywords


Biphasic hydroformylation; Cobalt complexes; 1-hexene; recycling; o-TPPTS

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Copyright (c) 2017 María Modroño-Alonso, William Castro, Francisco Lopez-Linares, Merlín Rosales, Pablo Jose Baricelli

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Journal of the Mexican Chemical Society (J. Mex. Chem. Soc.) Quarterly publication. Editor-in-Chief: Ignacio González-Martínez. Indexed Journal. Certificate of reserved rights granted by the Instituto Nacional del Derecho de Autor (INDAUTOR): 04-2005-052710530600-102. Certificate of lawful title and content: Under procedure. Postal registration of printed matter deposited by editors or agents granted by SEPOMEX: IM09-0312 Copyright © Sociedad Química de México, A.C. Total or partial reproduction is prohibited without written permission of the right holder. The Figures/schemes quality and the general contents of this publication are full responsability of the authors. Edited and distributed by Sociedad Química de México, A.C. Barranca del Muerto 26, Col. Crédito Constructor, Del. Benito Juárez, C.P. 03940, Mexico City. Phone: +5255 56626837; +5255 56626823 Contact: soquimex@sqm.org.mx http://www.sqm.org.mx