Highly selective hydrogenation of phenol and derivatives over a Pd@carbon nitride catalyst in aqueous media

J Am Chem Soc. 2011 Mar 2;133(8):2362-5. doi: 10.1021/ja109856y. Epub 2011 Feb 4.

Abstract

Cyclohexanone is an important intermediate in the manufacture of polyamides in chemical industry, but direct selective hydrogenation of phenol to cyclohexanone under mild conditions is a challenge. We report here a catalyst made of Pd nanoparticles supported on a mesoporous graphitic carbon nitride, Pd@mpg-C(3)N(4), which was shown to be highly active and promoted the selective formation of cyclohexanone under atmospheric pressure of hydrogen in aqueous media without additives. Conversion of 99% and a selectivity higher than 99% were achieved within 2 h at 65 °C. The reaction can be accelerated at higher temperature, but even at room temperature, 99% conversion and 96% selectivity could still be obtained. The generality of the Pd@mpg-C(3)N(4) catalyst for this reaction was demonstrated by selective hydrogenation of other hydroxylated aromatic compounds with similar performance.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclohexanones / chemical synthesis*
  • Cyclohexanones / chemistry
  • Hydrogen / chemistry*
  • Hydrogenation
  • Molecular Structure
  • Nanoparticles / chemistry
  • Nitriles / chemistry*
  • Palladium / chemistry*
  • Particle Size
  • Phenols / chemistry*
  • Porosity
  • Surface Properties
  • Temperature
  • Water / chemistry

Substances

  • Cyclohexanones
  • Nitriles
  • Phenols
  • Water
  • cyanogen
  • cyclohexanone
  • Palladium
  • Hydrogen