New Formula for the Hydrogen-Bonding Hansen Component of Methanol, Ethanol, and n-Propanol for Non-ambient Conditions-Application in Gas Antisolvent Fractionation-Based Optical Resolution.

Máté Mihalovits,Márton Kőrösi,Edit Székely

doi:10.1021/acsomega.1c02223

Máté Mihalovits, Márton Kőrösi + Show 1 more

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https://doi.org/10.1021/acsomega.1c02223

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Journal: ACS omega	Publication Date: Jul 12, 2021
Citations: 3	License type: CC BY 4.0

Affiliation: Budapest University of Technology and Economics

Abstract

Optical resolution by diastereomeric salt formation based on gas antisolvent fractionation is influenced by the chemical equilibrium of the salt formation, the solubility, and the extraction of the compounds. Selectivity, also known as resolution efficiency, is highly solvent-dependent and is also affected by process parameters both in atmospheric and supercritical processes. For the first time in the literature, a mathematical model that employs all three Hansen parameters and operating parameters is constructed to describe the selectivity of a gas antisolvent fractionation process. The satisfying goodness of fit of the models suggests that the outcome of the three subprocesses in the gas antisolvent fractionation process (i.e., salt formation reaction, precipitation, and extraction) can be described in a single model. A new formula for pressure and temperature correction of the hydrogen-bonding component of the Hansen parameter for non-ambient conditions for liquid methanol, ethanol, and n-propanol is also suggested in this paper.

Highlights

Solubility parameters are physical−chemical indexes that characterize the intermolecular forces in substances
The materials, the applied method, and the results for the gas antisolvent fractionation (GASF)-based resolution of mandelic acid with (R)-1-methylbenzylamine can be found in the study by Kőrösi et al.,[26] while the experiments with ibuprofen and methanol can be found in the study by Lőrincz et al.[28]
Mathematical model building with the purpose of description of selectivity of GASF-based optical resolution is performed in this paper

Summary

Introduction

Solubility parameters are physical−chemical indexes that characterize the intermolecular forces in substances. Application of solubility parameters enables to predict to what extent two substances can be mixed. They are widely used in different fields where solubility is of importance, for example, cocrystal formulation (Mohammad et al.1), polymer chemistry (Hansen2), the solubility of bitumen (Redelius3), extraction (Srinivas et al.4), and coating formulation (Hansen[5]). The Hildebrand parameter is a widely applied and convenient index for dissolution in liquids with nonpolar and slightly polar nature (e.g., solubility of polymers in organic solvents), the application of the parameter is limited due to the lack of capability to differentiate between the types of intermolecular interactions. Hansen[7] extended the concept of the Hildebrand solubility parameter by partitioning the molar energy of vaporization into three components

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