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Study of the characterization and crystallization of 4‐hydroxy‐2‐pyrrolidone
Author(s) -
Wang Xiu Juan,
Wiehler Harald,
Ching Chi Bun
Publication year - 2004
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20021
Subject(s) - 2 pyrrolidone , chemistry , differential scanning calorimetry , crystallization , melting point , solubility , enantiomer , phase diagram , ternary operation , crystallography , powder diffraction , fourier transform infrared spectroscopy , phase (matter) , stereochemistry , organic chemistry , thermodynamics , chemical engineering , physics , computer science , programming language , engineering
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. Chirality 16:220–227, 2004 . © 2004 Wiley‐Liss, Inc.