Abstract

Most pharmaceuticals are stereoisomers that each enantiomer shows dramatically different biological activity. Therefore, the production of optically pure chemicals through sustainable and energy-efficient technology is one of the main objectives in the pharmaceutical industry. Membrane-based separation is a continuous process performed on a large scale that uses far less energy than the conventional thermal separation process. Enantioselective polymer membranes have been developed for chiral resolution of pharmaceuticals; however, it is difficult to generate sufficient enantiomeric excess (ee) with conventional polymers. This article describes a chiral resolution strategy using a composite structure of mixed matrix membrane that employs chiral fillers. We discuss several enantioselective fillers, including metal-organic frameworks (MOFs), covalent organic frameworks (COFs), zeolites, porous organic cages (POCs), and their potential use as chiral fillers in mixed matrix membranes. State-of-the-art enantioselective mixed matrix membranes (MMMs) and the future design consideration for highly efficient enantioselective MMMs are discussed.

Highlights

  • Among various types of membranes, we focus on the enantioselective mixed matrix membrane (MMM), which possesses the advantages of both a solution-processable polymeric matrix and a highly enantioselective microporous filler

  • The organic solvent nanofiltration (OSN) performance of MMM can be improved via further modifications, such as the in situ growth of HKUST–1 within the pores of the P84 membrane, or by introducing carboxylate functional groups to increase the degree of adhesion of HKUST–1 to the membranes, which achieved a molecular weight cutoff of 794 g/mol [37]

  • Since chiral covalent organic frameworks (COFs) have the potential to separate enantiomers based on their chiralities [69,70,72], it is reasonable to expect that COFs can be utilized as filler particles in enantioselective mixed matrix membranes [70]

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Summary

Introduction

Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. In the last few decades, four conventional chiral resolution methods have been developed: crystallization, kinetic separation, chromatography, and membrane-based separation. Kinetic separation, and chromatography have been extensively investigated, the existing chiral resolution methods still utilize batch technology. The shift towards continuous manufacturing in the pharmaceutical and food industries provides an opportunity for steady-state, enantioselective membrane-based separations to emerge as a platform technology for large-scale chiral resolution. We discuss several enantioselective microporous materials, including metal-organic frameworks (MOFs), covalent organic frameworks (COFs), zeolites, porous organic cages (POCs), and their potential use as chiral fillers in MMMs. we introduce the fabrication methods and enantiomeric separation performances of state-of-the-art enantioselective MMMs. Future design considerations for the enantioselective MMMs are suggested in the last section to implement highly efficient, large-scale enantiomeric separations

Towards A Membrane-Based Chiral Resolution
Transport Mechanisms in Enantioselective Membranes
Chiral
Chiral Filler
Filler
Other Composite Mixed Matrix Membrane
Findings
Prospects for Designing Enantioselective MMMs
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