The Influence of the Solid Solution Formation on Purification of L-Menthol from the Enantiomer Mixture by Three-Phase Crystallization

Abstract

Three-phase crystallization (TPC) was introduced in this study to purify L-menthol from menthol enantiomer mixtures in consideration of the formation of solid solutions. TPC is a new separation technology, which combines melt crystallization and vaporization to result in the desired crystalline product from a liquid mixture along with the unwanted components vaporized via the three-phase transformation by reducing temperature and pressure. The three-phase transformation conditions for the liquid menthol enantiomer mixtures were determined based on the thermodynamic calculations to direct the TPC experiments. A new model was proposed based on the mass and energy balances in consideration of the formation of the solid solutions to predict the yield and purity of the final L-menthol product during TPC. The yield and purity obtained from the TPC experiments were compared with those predicted by the model.

Research Progress on Extraction, Separation, and Purification Methods of Plant Essential Oils

“…Actually, it is a mixture separated from peppermint oil and can also be artificially synthesized [100]. To merely bio-catalytically resolve L-menthol with an analgesic effect from the menthol enantiomer, Hsu Y C et al [101] applied the TPC method and determined the conditions for the liquid menthol enantiomer mixtures based on the thermodynamic calculations. It turned out that L-menthol was isolated from the mixtures successfully and the experimental purity of the final product was consistent with that predicted by the model proposed based on the mass and energy balances, although the experimental yield was slightly lower than that of the model [102].…”

Separation and nucleation kinetics of l-menthol polymorph through a swift cooling crystallization process

“…13 Yu-Chao Hsu et al introduced a new separation technology of a three phase crystallization process to study the purification of l -menthol from menthol enantiomer mixtures from solid solution formation. 14 With the cooling crystallization process, pharmaceutical cocrystals that are multi-component substances formulated to enhance the properties of active pharmaceutical ingredients (APIs) and are commercially used to enhance several drug additives successfully through the drug discovery pipeline, this new technology expands to access new solid forms. 15 An important idea for the development of new food products, based on further control and application of cocrystallization techniques is useful in the food industry with unique properties.…”