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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen


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Volume 91, Issue 10

Issues

Heterogeneous palladium SALOPHEN onto porous polymeric microspheres as catalysts for heck reaction

Claudio Mella
  • Departamento de Físico-Química, Facultad de Ciencias Químicas, Universidad de Concepción, Edmundo Larenas 129, Concepción, Chile
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Cecilia C. Torres
  • Departamento de Ciencias Químicas, Facultad de Ciencias Exactas, Universidad Andres Bello, Sede Concepción, Autopista Concepción-Talcahuano 7100, Talcahuano, Chile
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Cyril Godard / Carmen Claver / Gina Pecchi
  • Departamento de Físico-Química, Facultad de Ciencias Químicas, Universidad de Concepción, Edmundo Larenas 129, Concepción, Chile
  • Millenium Nuclei on Catalytic Processes Towards Sustainable Chemistry (CSC), Concepción, Chile
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Cristian H. Campos
  • Corresponding author
  • Departamento de Físico-Química, Facultad de Ciencias Químicas, Universidad de Concepción, Edmundo Larenas 129, Concepción, Chile
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  • Other articles by this author:
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Published Online: 2019-08-07 | DOI: https://doi.org/10.1515/pac-2018-1225

Abstract

Catalysts based on porous polymeric microspheres were prepared from N,N′-Bis(3,3′-allyl-salicylidene)-o-phenylenediamine Pd(II) (PdAS) metallo-monomer, styrene (STY), and divinylbenzene (DVB) as co-monomers. The effects of the STY/PdAS mass ratio of co-monomers were investigated to synthesize the optimal catalyst. All the prepared materials were characterized by scanning electron microscopy (SEM), N2 adsorption-desorption isotherms, inductively coupled plasma optical emission spectroscopy (ICP-OES), thermogravimetric analysis (TGA), solid-state diffuse-reflectance UV Vis (DRS UV-Vis) spectrometry, and X-ray photoelectron spectroscopy (XPS). Increasing the PdAS content from 1 to 5 wt%, based on the mass feed of monomers, produced well-defined spherical polymer resins with particle diameters of ~200 μm and high surface areas (>500 m2/g). XPS spectra shown a unique Pd2+ signal associated with the PdAS complex immobilized on a porous resin matrix. The catalytic performances of porous polymer microspheres were evaluated for Heck reaction between iodobenzene and methyl acrylate to produce methyl cinnamate, giving up to 100 % selectivity for the trans-isomer. The resin with 5 wt% PdAS showed the best catalytic activity in methyl cinnamate synthesis. Finally, the best catalytic system was evaluated in octinoxate production producing the target product with the same levels of conversion and selectivity for trans-isomer as was detected for methyl cinnamate synthesis.

This article offers supplementary material which is provided at the end of the article.

Keywords: cross-coupling reactions; Eurasia 2018; immobilization; microsphere resins; palladium catalysis; porous polymers

Article note

A collection of invited papers based on presentations at the 15th Eurasia Conference on Chemical Sciences (EuAsC2S-15) held at Sapienza University of Rome, Italy, 5–8 September 2018.

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About the article

Published Online: 2019-08-07

Published in Print: 2019-10-25


Funding Source: CONICYT

Award identifier / Grant number: 21150195

The authors thank CONICYT FONDECYT 1170083, FONDECYT 11170095, FONDECYT 11160468 and Unidad de Equipamiento Científico – MAINI, Universidad Católica del Norte, for the XPS analysis (Conicyt-Programa FONDEQUIP XPS EQM 140044 2014-2016). C. Mella thanks to CONICYT Grant 21150195 for his PhD fellowship. C.C. Torres thanks to CONICYT, PAI/Concurso Nacional inserción de Capital Humano Avanzado en la Academia Convocatoria año 2017 PAI79170027. The authors thank to Dr. Joel B. Alderete of the Instituto de Química de Recursos Naturales – Universidad de Talca, Chile for his collaboration with the ESI-MS/MS analysis.


Citation Information: Pure and Applied Chemistry, Volume 91, Issue 10, Pages 1651–1664, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1515/pac-2018-1225.

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