Rational approach to the selection of conditions for diastereomeric resolution of chiral amines by diacid resolving agents
This paper presents an experimental and modelling approach to understanding the key conditions for diastereomeric resolutions of chiral amines by diacid resolving agents. The model is used to calculate resolution yields and enantiomeric excesses on the basis of acid–base chemical equilibria, forma...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2006
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| Online Access: | http://eprints.utm.my/3108/1/Nazlee_Tetra2.pdf |
| _version_ | 1796853519714615296 |
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| author | Ferreira, Frederico Ghazali, Nazlee Faisal Cocchini, Ugo Livingston, Andrew |
| author_facet | Ferreira, Frederico Ghazali, Nazlee Faisal Cocchini, Ugo Livingston, Andrew |
| author_sort | Ferreira, Frederico |
| collection | ePrints |
| description | This paper presents an experimental and modelling approach to understanding the key conditions for diastereomeric resolutions of chiral amines by diacid resolving agents. The model is used to calculate resolution yields and enantiomeric excesses on the basis of acid–base chemical equilibria, formation of diastereomeric salts and their solubilities. Model parameters were determined experimen-
tally and used to model predicted process variables, which were then compared to experimental resolution data as a function of the resolving agents/amine molar ratio. Based on this model, suggestions for the rational design of diastereomeric resolutions are made, highlighting the benefits of employing molar ratios higher than 1.5.
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| first_indexed | 2024-03-05T18:00:43Z |
| format | Article |
| id | utm.eprints-3108 |
| institution | Universiti Teknologi Malaysia - ePrints |
| language | English |
| last_indexed | 2024-03-05T18:00:43Z |
| publishDate | 2006 |
| publisher | Elsevier |
| record_format | dspace |
| spelling | utm.eprints-31082010-06-01T03:07:18Z http://eprints.utm.my/3108/ Rational approach to the selection of conditions for diastereomeric resolution of chiral amines by diacid resolving agents Ferreira, Frederico Ghazali, Nazlee Faisal Cocchini, Ugo Livingston, Andrew TP Chemical technology This paper presents an experimental and modelling approach to understanding the key conditions for diastereomeric resolutions of chiral amines by diacid resolving agents. The model is used to calculate resolution yields and enantiomeric excesses on the basis of acid–base chemical equilibria, formation of diastereomeric salts and their solubilities. Model parameters were determined experimen- tally and used to model predicted process variables, which were then compared to experimental resolution data as a function of the resolving agents/amine molar ratio. Based on this model, suggestions for the rational design of diastereomeric resolutions are made, highlighting the benefits of employing molar ratios higher than 1.5. Elsevier 2006 Article PeerReviewed application/pdf en http://eprints.utm.my/3108/1/Nazlee_Tetra2.pdf Ferreira, Frederico and Ghazali, Nazlee Faisal and Cocchini, Ugo and Livingston, Andrew (2006) Rational approach to the selection of conditions for diastereomeric resolution of chiral amines by diacid resolving agents. Tetrahedron: Asymmetry, 17 (9). pp. 1337-1348. ISSN 0957-4166 http://dx.doi.org/10.1016/j.tetasy.2006.04.036 10.1016/j.tetasy.2006.04.036 |
| spellingShingle | TP Chemical technology Ferreira, Frederico Ghazali, Nazlee Faisal Cocchini, Ugo Livingston, Andrew Rational approach to the selection of conditions for diastereomeric resolution of chiral amines by diacid resolving agents |
| title | Rational approach to the selection of conditions for diastereomeric resolution of chiral amines by diacid resolving agents |
| title_full | Rational approach to the selection of conditions for diastereomeric resolution of chiral amines by diacid resolving agents |
| title_fullStr | Rational approach to the selection of conditions for diastereomeric resolution of chiral amines by diacid resolving agents |
| title_full_unstemmed | Rational approach to the selection of conditions for diastereomeric resolution of chiral amines by diacid resolving agents |
| title_short | Rational approach to the selection of conditions for diastereomeric resolution of chiral amines by diacid resolving agents |
| title_sort | rational approach to the selection of conditions for diastereomeric resolution of chiral amines by diacid resolving agents |
| topic | TP Chemical technology |
| url | http://eprints.utm.my/3108/1/Nazlee_Tetra2.pdf |
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