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Wang XJ, Wiehler H, Ching CB. Study of the characterization and crystallization of 4-hydroxy-2-pyrrolidone. Chirality. 2004;16(4):220-7doi: 10.1002/chir.20021.
Wang, X. J., Wiehler, H., & Ching, C. B. (2004). Study of the characterization and crystallization of 4-hydroxy-2-pyrrolidone. Chirality, 16(4), 220-7. https://doi.org/10.1002/chir.20021
Wang, Xiu Juan, et al. "Study of the characterization and crystallization of 4-hydroxy-2-pyrrolidone." Chirality vol. 16,4 (2004): 220-7. doi: https://doi.org/10.1002/chir.20021
Wang XJ, Wiehler H, Ching CB. Study of the characterization and crystallization of 4-hydroxy-2-pyrrolidone. Chirality. 2004 May 05;16(4):220-7. doi: 10.1002/chir.20021. PMID: 15034904.
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Chirality. 2004 May 05;16(4):220-7. doi: 10.1002/chir.20021.

Study of the characterization and crystallization of 4-hydroxy-2-pyrrolidone.

Chirality

Xiu Juan Wang, Harald Wiehler, Chi Bun Ching

Affiliations

  1. Chemical and Process Engineering Centre, National University of Singapore, Singapore. [email protected]

PMID: 15034904 DOI: 10.1002/chir.20021

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 degrees 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 degrees C. The optical resolution of (+/-)-4-hydroxy-2-pyrrolidone was successfully achieved by preferential crystallization.

Copyright 2004 Wiley-Liss, Inc.

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