Catalytic Synthesis of Triaryl Phosphates from White Phosphorus

Kenneth Mark Armstrong, Petr Kilian

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

Triaryl phosphates were synthesized from white phosphorus and phenols under aerobic conditions and in the presence of iron catalysts and iodine. Full conversion to phosphates was achieved without the use of chlorine, and the reactions do not produce acid waste. Triphenyl phosphate, tritolyl phosphate and tris(2,4-di-tert-butyl) phenyl phosphate were synthesized by this method with high selectivities. Various iron(III) diketonates were used to catalyze the conversion. Mechanistic studies showed that the reaction proceeds by formation of PI3, then O=PI(OPh)(2) before the final formation of the phosphate. The nucleophilic substitution of O=PI(OPh)(2) with phenol to form O=P(OPh)(3) was found to be the rate-limiting step.

Original languageEnglish
Pages (from-to)2138-2147
Number of pages10
JournalEuropean Journal of Inorganic Chemistry
Volume2011
Issue number13
DOIs
Publication statusPublished - May 2011

Keywords

  • Homogeneous catalysis
  • Phosphorus
  • Flame retardants
  • Triaryl phosphates
  • Green chemistry
  • TRANSITION-METAL-COMPLEXES
  • ORGANOPHOSPHORUS COMPOUNDS
  • ELECTROCHEMICAL SYNTHESIS
  • P-4 ACTIVATION
  • FUNCTIONALIZATION
  • OXIDATION

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