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

Claudio Mella, Cecilia C. Torres, Cyril Godard, Carmen Claver, Gina Pecchi, Cristian H. Campos

Resultado de la investigación: Article

Resumen

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.

Idioma originalEnglish
PublicaciónPure and Applied Chemistry
DOI
EstadoPublished - 1 ene 2019

Huella dactilar

Palladium
Microspheres
divinyl benzene
Styrene
Resins
Monomers
Isomers
Catalysts
Polymers
X ray photoelectron spectroscopy
Optical emission spectroscopy
Inductively coupled plasma
Spectrometry
Isotherms
Thermogravimetric analysis
Catalyst activity
Desorption
Adsorption
Scanning electron microscopy
methyl cinnamate

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Citar esto

Mella, Claudio ; Torres, Cecilia C. ; Godard, Cyril ; Claver, Carmen ; Pecchi, Gina ; Campos, Cristian H. / Heterogeneous palladium SALOPHEN onto porous polymeric microspheres as catalysts for heck reaction. En: Pure and Applied Chemistry. 2019.
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title = "Heterogeneous palladium SALOPHEN onto porous polymeric microspheres as catalysts for heck reaction",
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.",
keywords = "cross-coupling reactions, Eurasia 2018, immobilization, microsphere resins, palladium catalysis, porous polymers",
author = "Claudio Mella and Torres, {Cecilia C.} and Cyril Godard and Carmen Claver and Gina Pecchi and Campos, {Cristian H.}",
year = "2019",
month = "1",
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doi = "10.1515/pac-2018-1225",
language = "English",
journal = "Pure and Applied Chemistry",
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Heterogeneous palladium SALOPHEN onto porous polymeric microspheres as catalysts for heck reaction. / Mella, Claudio; Torres, Cecilia C.; Godard, Cyril; Claver, Carmen; Pecchi, Gina; Campos, Cristian H.

En: Pure and Applied Chemistry, 01.01.2019.

Resultado de la investigación: Article

TY - JOUR

T1 - Heterogeneous palladium SALOPHEN onto porous polymeric microspheres as catalysts for heck reaction

AU - Mella, Claudio

AU - Torres, Cecilia C.

AU - Godard, Cyril

AU - Claver, Carmen

AU - Pecchi, Gina

AU - Campos, Cristian H.

PY - 2019/1/1

Y1 - 2019/1/1

N2 - 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.

AB - 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.

KW - cross-coupling reactions

KW - Eurasia 2018

KW - immobilization

KW - microsphere resins

KW - palladium catalysis

KW - porous polymers

UR - http://www.scopus.com/inward/record.url?scp=85070637745&partnerID=8YFLogxK

U2 - 10.1515/pac-2018-1225

DO - 10.1515/pac-2018-1225

M3 - Article

AN - SCOPUS:85070637745

JO - Pure and Applied Chemistry

JF - Pure and Applied Chemistry

SN - 0033-4545

ER -