New PDF release: Advances in Crystallization Processes

By Y. Mastai

ISBN-10: 9535105817

ISBN-13: 9789535105817

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Anal. 1997, 48, 691. : Tetrahedron Lett. 1980, 21, 647. [19] Pasteur, L. Acad. , 1848, 26, 535. : Termal. Anal. 1988, 33, 1241. : J. Chem. Soc. Perkin Trans 2, 2000, 149. : Tetrahedron: Asymm. 2000, 11, 809. ; Simon, H;. : Chirality 2001, 13, 29. : PhD disz. 2003 [25] a). ; Fogassy, E. b). Hung. Pat. no. ; Böcskei, Zs. Chirality, 1994, 6, 314 [27] Kassai, Cs: PhD diss. : Tetrahedron Letters, 1994, 35, 257260 . :. Tetrahedron: Asymmetry. 2008, 19, 1587. ; J. Pract. Chem. 1986, 336, 628. : J. Mol.

In such cases, either the crystallizing diastereoisomer or the one remained in the mother liquor form stable solvate with one of the solvents. After a short summary of the theoretical background, it will be shown via examples, how can we use the influence of pH, solvent polarity, and solvate formation, respectively, to improve the efficiency of enantiomeric separation. 33 The equilibrium model of a resolution of DL racemic base with an acidic resolving agent (RH) can be outlined bellow. 25 Separation of the Mixtures of Chiral Compounds by Crystallization PD PL solid KsD KsL liquid DL + 2RH DHR + LHR KdD D + H Kb DH + R + R Ka KdL + LH Kb L+H + 2H 2RH Where Ks = salt solubility constant, Kd = salt dissociation constant, Kb = base dissociation constant, Ka = acid dissociation constant, PD and PL are the precipitated diastereoisomeric salts, respectively.

The enantiomeric mixtures are isolated from the diastereoisomers and they are enriched to the desired ee values by applying one of the previously discussed methods. It has to be mentioned, that the enantiomeric mixture found in the crystalline diastereoisomer is usually much purer than that is isolated from the filtrate. Pope and Peachey38 have been recognized that if the half of the resolving agent necessary for the better soluble diasteroisomer is replaced by an achiral reagent (having the same chemical character as it is for the resolving agent) the less soluble diastereoisomer will be 21 Separation of the Mixtures of Chiral Compounds by Crystallization crystallized and the other isomer remains in the solution as a salt of the applied achiral additive.

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Advances in Crystallization Processes by Y. Mastai


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