New Sustainable Pd(II)/Fe(III) Catalytic System Very Efficient in the Hydromethoxycarbonylation of 1-octene

Authors

  • Andrea Vavasori
    Affiliation
    Department of Molecular Sciences and Nanosystems, Ca' Foscari University of Venice, via Torino 155, 30172 Mestre-Venice, Italy
  • Beatrice Fantinel
    Affiliation
    Department of Molecular Sciences and Nanosystems, Ca' Foscari University of Venice, via Torino 155, 30172 Mestre-Venice, Italy
  • Lucio Ronchin
    Affiliation
    Department of Molecular Sciences and Nanosystems, Ca' Foscari University of Venice, via Torino 155, 30172 Mestre-Venice, Italy
  • Francesco Zanrosso
    Affiliation
    Department of Molecular Sciences and Nanosystems, Ca' Foscari University of Venice, via Torino 155, 30172 Mestre-Venice, Italy
  • Marat Bulybayev
    Affiliation
    Department of Chemistry and Chemical Technology, Al-Farabi Kazakh National University, al-Farabi 71, 050038 Almaty, Kazakhstan
  • Nurbolat Kudaibergenov
    Affiliation
    Department of Chemistry and Chemical Technology, Al-Farabi Kazakh National University, al-Farabi 71, 050038 Almaty, Kazakhstan
  • Kairzhan Shalmagambetov
    Affiliation
    Department of Chemistry and Chemical Technology, Al-Farabi Kazakh National University, al-Farabi 71, 050038 Almaty, Kazakhstan
  • Gulbanu Zhaksylykova
    Affiliation
    Department of Chemistry and Chemical Technology, Al-Farabi Kazakh National University, al-Farabi 71, 050038 Almaty, Kazakhstan
https://doi.org/10.3311/PPch.22887

Abstract

In order to increase the catalytic activity of the Pd(II)-complexes in the alcoxycarbonylation of 1-olefins, the presence in solution of a strong Brönsted acid together with a phosphine ligand is usually required. From an industrial point of view, such two additives, however, influenced the sustainability of the process mainly caused by the related corrosion of the reaction vessel and the toxicity of the phosphine ligand.
In this paper, the methoxycarbonylation of 1-octene has been efficiently carried out by using the [Pd(TsO)2(PPh3)2]/FeCl3 catalyst system. The catalyst is very active also without addition of PPh3, reaching the TON of ca. 1300 (mol/mol) in 2 hours by using the
Fe(III)/Pd(II) = 400/1 (mol/mol) system. Such value is higher than the values obtained by using the traditional strong Brönsted acid TsOH or other Lewis acid such as AlCl3, in the presence of PPh3. The reaction takes place with the formation of two isomeric products of linear and branched structures with a yield towards the linear isomer of ca. 80%.

Keywords:

palladium catalyst, 1-octene, triphenylphosphine, carbon monoxide, hydromethoxycarbonylation, iron trichloride

Citation data from Crossref and Scopus

Published Online

2024-02-28

How to Cite

Vavasori, A., Fantinel, B., Ronchin, L., Zanrosso, F., Bulybayev, M., Kudaibergenov, N. “New Sustainable Pd(II)/Fe(III) Catalytic System Very Efficient in the Hydromethoxycarbonylation of 1-octene”, Periodica Polytechnica Chemical Engineering, 68(1), pp. 16–22, 2024. https://doi.org/10.3311/PPch.22887

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