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You separate the diastereomers by recrystallization. Then you regenerate the original acids by adding hydrochloric acid. Finally, you can separate enantiomers by chromatography using a chiral stationary phase. The R enantiomer will interact more strongly with an R stationary phase.
This is a general, three steps, technique for separating enantiomers: React the enantiomers with a single enantiomer of another compound to form diastereomers. Separate the diastereomers by conventional means (chromatography, recrystallization) Regenerate the original enantiomers, now separated.
Because the physical properties of enantiomers are identical, they seldom can be separated by simple physical methods, such as fractional crystallization or distillation.
This is possible because enantiomers have shared physical properties such as melting point and boiling point, but diastereomers have different chemical properties, so they can be separated like any two different molecules.
In chiral chromatography, silica gel is bonded to chiral molecules to form what is called a chiral stationary phase. The enantiomers will then separate as they run down the column because one of the enantiomers will interact more strongly with the column and “stick” in place.
3:12 5:01 Suggested clip Resolution of enantiomers | Chemical processes | MCAT | Khan YouTubeStart of suggested client of suggested clip Resolution of enantiomers | Chemical processes | MCAT | Khan
A simple way to separate enantiomers is to use a chiral column. However by the addition of an enantiomer (e.g. tartaric acid) to the mobile phase or by derivatization of the sample, it is possible to achieve a chiral separation on a non-chiral column.
Diastereomers have different degrees of attraction to a stationary phase. You can separate them on a suitable column. HPLC uses pressure to force a solvent containing the sample mixture through a column filled with a solid stationary phase.
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