Synthesis of diaryl phosphates using phytic acid as a phosphorus source

Phytic acid is a phosphorus-rich molecule, which is produced by plants using water-soluble phosphates absorbed from soil. It can potentially serve as a phosphorus source in the syntheses of organic phosphates; however, this approach has not been utilized for the preparation of phosphate esters. In this study, we report the first successful synthesis of phosphate esters using phytic acid as a phosphorus source. Crude products of phosphate diesters were obtained through the reactions of commercially available phytic acid and aromatic alcohols with 31 P nuclear magnetic resonance yields up to 83%. We also isolated a portion of the reaction substrates with yields up to 60%. Next, we extracted phytic acid from rice bran with a recovery of 4.2% and then conducted an esterification reaction using the extracted phytic acid and phenol. As a result, diphenyl phosphate with a yield of 44% was obtained. This work can facilitate the development of an environmentally friendly method for producing phosphate esters that does not rely on phosphate rock but instead uses biomass as a phosphorus source.