Gas Antisolvent Approach for the Precipitation of α -Methoxyphenylacetic Acid – ( R )-1-Cyclohexylethylamine Diateromeric Salt
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 min...
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Croatian Society of Chemical Engineers
2017-10-01
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| Series: | Chemical and Biochemical Engineering Quarterly |
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| Online Access: | http://silverstripe.fkit.hr/cabeq/assets/Uploads/14-3-17.pdf |
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| author | A. Zodge M. Kőrösi M. Tárkányi J. Madarász I. Miklós Szilágyi T. Sohajda E. Székely |
| author_facet | A. Zodge M. Kőrösi M. Tárkányi J. Madarász I. Miklós Szilágyi T. Sohajda E. Székely |
| author_sort | A. Zodge |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-22T10:18:55Z |
| format | Article |
| id | doaj.art-1cad1c4c15504703b52e4973cf410fd2 |
| institution | Directory Open Access Journal |
| issn | 0352-9568 1846-5153 |
| language | English |
| last_indexed | 2024-12-22T10:18:55Z |
| publishDate | 2017-10-01 |
| publisher | Croatian Society of Chemical Engineers |
| record_format | Article |
| series | Chemical and Biochemical Engineering Quarterly |
| spelling | doaj.art-1cad1c4c15504703b52e4973cf410fd22022-12-21T18:29:40ZengCroatian Society of Chemical EngineersChemical and Biochemical Engineering Quarterly0352-95681846-51532017-10-0131333534110.15255/CABEQ.2016.1023Gas Antisolvent Approach for the Precipitation of α -Methoxyphenylacetic Acid – ( R )-1-Cyclohexylethylamine Diateromeric SaltA. Zodge0M. Kőrösi1M. Tárkányi2J. Madarász3I. Miklós Szilágyi4T. Sohajda5E. Székely6Department of Chemical and Environmental Process Engineering, Budapest University of Technology and Economics, Budapest, HungaryDepartment of Chemical and Environmental Process Engineering, Budapest University of Technology and Economics, Budapest, HungaryDepartment of Chemical and Environmental Process Engineering, Budapest University of Technology and Economics, Budapest, HungaryDepartment of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, Budapest, Hungaryb) Department of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, Budapest, Hungary c) MTA-BME Technical Analytical Chemistry Research Group, Budapest, HungaryCYCLOLAB Ltd., Budapest, HungaryDepartment of Chemical and Environmental Process Engineering, Budapest University of Technology and Economics, Budapest, HungaryOne 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.http://silverstripe.fkit.hr/cabeq/assets/Uploads/14-3-17.pdfsupercritical CO 2optical resolutionα-methoxyphenylacetic acidcapillary electrophoresis |
| spellingShingle | A. Zodge M. Kőrösi M. Tárkányi J. Madarász I. Miklós Szilágyi T. Sohajda E. Székely Gas Antisolvent Approach for the Precipitation of α -Methoxyphenylacetic Acid – ( R )-1-Cyclohexylethylamine Diateromeric Salt Chemical and Biochemical Engineering Quarterly supercritical CO 2 optical resolution α-methoxyphenylacetic acid capillary electrophoresis |
| title | Gas Antisolvent Approach for the Precipitation of α -Methoxyphenylacetic Acid – ( R )-1-Cyclohexylethylamine Diateromeric Salt |
| title_full | Gas Antisolvent Approach for the Precipitation of α -Methoxyphenylacetic Acid – ( R )-1-Cyclohexylethylamine Diateromeric Salt |
| title_fullStr | Gas Antisolvent Approach for the Precipitation of α -Methoxyphenylacetic Acid – ( R )-1-Cyclohexylethylamine Diateromeric Salt |
| title_full_unstemmed | Gas Antisolvent Approach for the Precipitation of α -Methoxyphenylacetic Acid – ( R )-1-Cyclohexylethylamine Diateromeric Salt |
| title_short | Gas Antisolvent Approach for the Precipitation of α -Methoxyphenylacetic Acid – ( R )-1-Cyclohexylethylamine Diateromeric Salt |
| title_sort | gas antisolvent approach for the precipitation of α methoxyphenylacetic acid r 1 cyclohexylethylamine diateromeric salt |
| topic | supercritical CO 2 optical resolution α-methoxyphenylacetic acid capillary electrophoresis |
| url | http://silverstripe.fkit.hr/cabeq/assets/Uploads/14-3-17.pdf |
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