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Chemical and Biochemical Engineering Quarterly, Vol. 31 No. 3, 2017.

Original scientific paper

https://doi.org/10.15255/CABEQ.2016.1023

Gas Antisolvent Approach for the Precipitation of α-Methoxyphenylacetic Acid –(R)-1-Cyclohexylethylamine Diastereomeric Salt

A. Zodge orcid id orcid.org/0000-0003-3194-5544 ; Department of Chemical and Environmental Process Engineering, Budapest University of Technology and Economics, Budapest, Hungary
M. Kőrösi orcid id orcid.org/0000-0002-1224-4788 ; Department of Chemical and Environmental Process Engineering, Budapest University of Technology and Economics, Budapest, Hungary
M. Tárkányi ; Department of Chemical and Environmental Process Engineering, Budapest University of Technology and Economics, Budapest, Hungary
J. Madarász ; Department of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, Budapest, Hungary
I. Miklós Szilágyi orcid id orcid.org/0000-0002-5938-8543 ; b) Department of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, Budapest, Hungary; c) MTA-BME Technical Analytical Chemistry Research Group, Budapest, Hungary
T. Sohajda ; CYCLOLAB Ltd., Budapest, Hungary
E. Székely orcid id orcid.org/0000-0002-6935-0071 ; Department of Chemical and Environmental Process Engineering, Budapest University of Technology and Economics, Budapest, Hungary

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Abstract

One of the major drawbacks of diastereomeric salt precipitation based enantioseparation is the time and solvent requirement of crystallization. In the gas antisolvent (GAS) approach, supercritical carbon dioxide is applied as an antisolvent, and the precipitation
takes place in a couple of minutes. By setting the process parameters diastereomeric excess, yields, and selectivity can be controlled. Applicability of the process is demonstrated on the resolution of racemic 2-methoxyphenylacetic acid with enantiopure (R)-(−)-1-cyclohexylethylamine. Diastereomeric excess values over 55 % along with 80 % yields were achieved at optimal conditions in a single step.







This work is licensed under a Creative Commons Attribution 4.0 International License.

Keywords

supercritical CO2; optical resolution; α-methoxyphenylacetic acid; capillary electrophoresis

Hrčak ID:

187146

URI

https://hrcak.srce.hr/187146

Publication date:

4.10.2017.

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