Separation Of Menthyl (Hydroxymethyl)-Phenyl Phosphinate Using Molecularly Imprinted Polymers

Abstract

Molecularly imprinted polymers (MIPs) are advantageous to chemists both in their ability to drive the equilibrium of a reaction toward a desired product and in chromatography. In this project we focused on the use of MIPs in a chromatographic sense to selectively isolate menthyl (hydroxymethyl)-phenyl phosphinate in the SP form from a mixture of both diastereoisomers. Both RP and SP configurations are made in equal proportions but the yield from isolation and crystallization of each pure diastereoisomer is ~25%. Production of a polymer containing pockets specific to the configuration of one diastereoisomer enables an easier method to isolate one diastereoisomer through absorption by the polymer and subsequent release. The potential for MIPs for these P-stereogenic compounds lies in the increased yield of pure crystals and therefore decreased cost of production.