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Title: Study of the Characterization and Crystallization of 4-Hydroxy-2-Pyrrolidone
Authors: Wang, X.J. 
Wiehler, H.
Ching, C.B. 
Keywords: 4-hydroxy-2-pyrrolidone
Metastable zone
Phase diagram
Preferential crystallization
Issue Date: 2004
Citation: Wang, X.J., Wiehler, H., Ching, C.B. (2004). Study of the Characterization and Crystallization of 4-Hydroxy-2-Pyrrolidone. Chirality 16 (4) : 220-227. ScholarBank@NUS Repository.
Abstract: A systematic study of the characterization for racemic species of 4-hydroxy-2-pyrrolidone was undertaken. The melting point phase diagram of (R)- and (S)-4-hydroxy-2-pyrrolidone was determined by differential scanning calorimetry. The ternary phase diagram of (R)- and (S)-4-hydroxy-2-pyrrolidone with isopropanol was constructed at 15, 20, 25, and 35°C. The crystalline nature of 4-hydroxy-2-pyrrolidone racemate was also characterized by means of comparison of solid-state FTIR spectra and powder X-ray diffraction patterns of the racemic mixture with those of one of the enantiomers. It is shown that (±)-4-hydroxy-2-pyrrolidone is a racemic conglomerate. The enthalpies of fusion of (R)-4-hydroxy-2-pyrrolidone and (±)-4-hydroxy-2-pyrrolidone and entropy of mixing of (R)- and (S)-4-hydroxy-2-pyrrolidone were calculated using the thermodynamic data. The solubility and supersolubility diagrams of (R)- and (S)-4-hydroxy-2-pyrrolidone in isopropanol were determined over a temperature range of 4-35°C. The optical resolution of (± )-4-hydroxy-2-pyrrolidone was successfully achieved by preferential crystallization. © 2004 Wiley-Liss, Inc.
Source Title: Chirality
ISSN: 08990042
DOI: 10.1002/chir.20021
Appears in Collections:Staff Publications

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