Highly active tin(iv) phosphate phase transfer catalysts for the production of lactic acid from triose sugars

Abstract

Lactic acid (LA) is an important intermediate in the fine chemical industry because it is utilized as a building block for the production of biodegradable plastics. In this study, a series of tin phosphate phase transfer catalysts modified with several surfactants have been prepared by a facile one-pot synthesis method and tested for the direct conversion of trioses to LA under hydrothermal conditions. Poly(ethylene glycol) (PEG) was identified as the most promising surfactant, and the product distribution closely depended on the reaction temperature, catalyst loading and substrate concentration. Complete DHA conversion and a good yield of up to 96.1% of LA were obtained at 140 °C after 4 h of reaction time. Pyridine FTIR demonstrated the presence of Brønsted and Lewis acid sites, which play crucial roles in the dehydration of DHA to pyruvaldehyde (PA) and the following isomerization of generated PA to LA. Furthermore, the isomerization of PA to LA was found to be the rate-determining step. A possible reaction mechanism was proposed: 1) the coordination between PEG and the metal ions caused a greater separation of the tin ions from the phosphate anions, making them more potent Lewis acid sites, and 2) the PEG behaved as a phase transfer catalyst during the reaction. This study paves the way for the further design of improved solid acid catalysts for aqueous phase production of LA from carbohydrates.