O-Carboxymethyl Chitosan Supported Heterogeneous Palladium and Ni Catalysts for Heck Reaction

Molecules. 2017 Jan 18;22(1):150. doi: 10.3390/molecules22010150.

Abstract

Two polymer catalysts (Pd-OCMCS and Ni-OCMCS) with good reusability were synthesized by coordinating Pd and Ni onto O-carboxymethyl chitosan (OCMCS). The chemical structure and thermal stability of prepared catalysts were determined by Fourier transform infrared (FT-IR) spectra, Energy Dispersive Spectrometer (EDS)analysis, X-ray diffraction (XRD), and thermogravimetric analyzer (TG-DTG), and the analysis results showed that the Pd and Ni ions coordinated onto the OCMCS and formed a ligand with the -COOH group, amino groups, and -OH group on the OCMCS, and the EDS and Inductively Coupled Plasma Optical Emission Spectrometry (ICP-OES) analysis results showed that the loading amounts of Pd and Ni were approximately 8.3% and 8.9%, respectively. In the Heck reaction between aryl halides and n-butyl acrylate catalyzed by the prepared catalyst, the test results showed that the product yield followed the order of aryl iodide > aryl bromide > aryl chloride. Additionally, the product yield for the aryl iodide and aryl bromide could reach up to 99% and 96%, respectively. Moreover, the electron-withdrawing and electron-donating property of the group on the aryl also affected the product yield, and the product yield for aryl halides with electron-withdrawing group p-NO₂, p-CH₃CO, and p-CHO was higher than that with electron-donating group p-CH₃.

Keywords: Ni-OCMCS; O-carboxymethyl chitosan; Pd-OCMCS; biopolymer-supported catalyst; heck reaction.

MeSH terms

  • Acrylates / chemistry*
  • Benzene Derivatives / chemistry*
  • Benzyl Compounds / chemistry
  • Catalysis
  • Chitosan / analogs & derivatives*
  • Chitosan / chemistry
  • Electrons*
  • Equipment Reuse
  • Microscopy, Electron, Scanning
  • Nickel / chemistry*
  • Palladium / chemistry*

Substances

  • Acrylates
  • Benzene Derivatives
  • Benzyl Compounds
  • O-carboxymethylchitosan
  • Palladium
  • n-butyl acrylate
  • Nickel
  • Chitosan
  • benzyl bromide