Resolution of racemic trans-1,2-cyclohexanediol with tartaric acid

Molnar, Peter; Thorey, Paul; Bánsághi, György; Székely, Edit; Poppe, László; Tomin, Anna; Kemény, Sándor; Fogassy, Elemér; Simándi, Béla

doi:10.1016/j.tetasy.2008.06.023

Cited by 14 publications

(7 citation statements)

References 41 publications

(36 reference statements)

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“…The selected resolving agent is added in less than stoichiometric ratio to the racemic compound. The unreacted enantiomers are extracted with the supercritical solvent, and are collected as a powder after depressurization of the solution [188]. resolving agent to racemic compound for both resolving agents (ee E = 82.5% and ee E = 57.9%, respectively).…”

Section: 1-application Of Sfe To Enantiomeric Separationsmentioning

confidence: 99%

Supercritical fluid extraction: Recent advances and applications

Herrero¹,

Mendiola²,

Cifuentes³

et al. 2010

Journal of Chromatography A

632

293

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Among the different extraction techniques used at analytical and preparative scale, supercritical fluid extraction (SFE) is one of the most used. This review covers the most recent developments of SFE in different fields, such as food science, natural products, by-product recovery, pharmaceutical and environmental sciences, during the period 2007-2009. The revision is focused on the most recent advances and applications in the different areas; among them, it is remarkable the strong impact of SFE to extract high value compounds from food and natural products but also its increasing importance in areas such as heavy metals recovery, enantiomeric resolution or drug delivery systems.

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Section: 1-application Of Sfe To Enantiomeric Separationsmentioning

confidence: 99%

Supercritical fluid extraction: Recent advances and applications

Herrero¹,

Mendiola²,

Cifuentes³

et al. 2010

Journal of Chromatography A

632

293

View full text Add to dashboard Cite

show abstract

“…This extraction can be accomplished using a supercritical uid, most oen supercritical carbon dioxide. In case of resolution of trans-cyclohexane-1,2-diol (trans-CHD) 25 by (R,R)tartaric acid ((R,R)-TA) the free enantiomeric portion was separated by extraction with supercritical CO 2 from the mixture of the excess of trans-CHD and the crystalline diastereoisomeric complex (Scheme 8). Of course, the other enantiomer can be recovered from the diastereoisomeric complex.…”

Section: Separation Of Diastereoisomers By Extraction Of Enantiomericmentioning

confidence: 99%

Prediction of the efficiency of diastereoisomer separation on the basis of the behaviour of enantiomeric mixtures

et al. 2014

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The driving force of homo-and heterochiral complex formation in mixtures of chiral compounds is, probably, the effort of the system to separate the most symmetric associates from the less symmetric ones. A possible way to achieve separation of these associates is distribution between two phases. Therefore, during the separation of (a certain part) diastereoisomers similar trends can be observed as in the course of the distribution of enantiomeric mixtures between two phases, although in the first case a third chiral compound (namely the resolving agent) is present. Of course in this case the pursuit of symmetry is not so obvious as in case of enantiomeric mixtures. It should be noted that the outcome may thus be modified by the intervention of kinetic control. One can conclude that the structure of chiral compounds encodes the result of the (optical) resolution.Scheme 3 The effect of the eutectic composition of racemic compound and resolving agent on the eutectic composition of diastereoisomers obtained (see also Scheme 2).Scheme 4 Separation from the melt.

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“…98% or higher enantiomeric excess values were achieved in certain cases only. [20][21][22] However, there is only limited information available on the applicability of antisolvent processes for the further purification by the antisolvent recrystallization of diastereomeric mixtures. [20,23] Mandelic acid is often used as a model molecule in investigations targeting chiral separation.…”

Section: Introductionmentioning

confidence: 99%

Gas Antisolvent Fractionation: a New Method to Obtain Enantiopure Compounds, a Case Study on Mandelic Acid

Kőrösi

Sedon

Komka

et al. 2018

Period. Polytech. Chem. Eng.

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Micronization processes involving supercritical carbon dioxide are rapid methods to produce fine particles. They also might offer the possibility of using less organic solvent than conventional crystallization methods leading to an environmentally friendlier processing. The separation capabilities of such processes are now demonstrated on the diastereomeric resolution of mandelic acid using (R)-1-phenylethanamine as a resolving agent, utilizing the batch type gas antisolvent fractionation as the separation method. A detailed study was conducted on the effects of the operational parameters pressure (12-20 MPa), temperature (35-55 °C) and co-solvent concentration (33-99 mg/ml). At 12 MPa, 35 °C and 99 mg/ml methanol concentration, a selectivity of 0.52 and a diastereomeric excess of 62% was reached. The same operational parameters were applied during the investigation of the recrystallization-based further purification of the diastereomeric salts, applying the resolving agent in molar equivalent quantity to a non-racemic mixture of mandelic acid. It has been found that the more stable (R)-1-phenylethylammonium-(R)-mandelate salt can be purified to de>98% through four additional recrystallization steps following the initial, half-molar equivalent resolution step.

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Resolution of racemic trans-1,2-cyclohexanediol with tartaric acid

Cited by 14 publications

References 41 publications

Supercritical fluid extraction: Recent advances and applications

Supercritical fluid extraction: Recent advances and applications

Prediction of the efficiency of diastereoisomer separation on the basis of the behaviour of enantiomeric mixtures

Gas Antisolvent Fractionation: a New Method to Obtain Enantiopure Compounds, a Case Study on Mandelic Acid

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