Effect of additives on the preferential crystallization of L-asparagine monohydrate

Peetikamol Kongsamai, Atthaphon Maneedaeng, Chalongsri Flood, Joop H. ter Horst, Adrian E. Flood

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Preferential Crystallization (PC) is a popular process to separate enantiomers, however the nucleation and growth of the counter enantiomer during the process can compromise the enantiopurity of the final crystalline product. This research investigates the use of additives to inhibit the nucleation and growth of the counter enantiomer. In this study, we use L-asparagine monohydrate (L-Asn·H2O) as the preferred enantiomer in crystallization from DL-Asn·H2O solutions. Additives include both pure enantiomers of several related amino acid species. This allows investigation of differences in inhibition caused by additives that are of the same chirality and different chirality as the preferred enantiomer. The additives had no discernible effect on the solubility but had a small effect on the metastable limit, with additives tending to slightly widen the metastable zone but also make the zone widths more disperse. D-additives have a small effect on the growth rate of L-Asn·H2O but L-Asp and L-Glu strongly inhibit the growth rate of L-Asn·H2O in DL-Asn·H2O solution; there must also be a corresponding effect for D-Asp and D-Glu on D-Asn·H2O. Indeed, PC experiments showed that in order to obtain L-Asn·H2O from a PC while preventing the formation of D-Asn·H2O, D-Asp and D-Glu are suitable additives, leading to high yield and purity of pure L-Asn·H2O.

LanguageEnglish
Pages823-835
Number of pages13
JournalEuropean Physical Journal: Special Topics
Volume226
Issue number5
Early online date18 Apr 2017
DOIs
Publication statusE-pub ahead of print - 18 Apr 2017

Fingerprint

Asparagine
Crystallization
Enantiomers
enantiomers
crystallization
Chirality
chirality
counters
Nucleation
nucleation
amino acids
Amino acids
purity
solubility
Solubility
Crystalline materials
Amino Acids
products

Keywords

  • preferential crystallization
  • aspargine monohydrate
  • enantiomers
  • amino acids
  • efficiency
  • yield
  • additives
  • solubility
  • metastable zone
  • growth rate.

Cite this

Kongsamai, Peetikamol ; Maneedaeng, Atthaphon ; Flood, Chalongsri ; ter Horst, Joop H. ; Flood, Adrian E. / Effect of additives on the preferential crystallization of L-asparagine monohydrate. In: European Physical Journal: Special Topics. 2017 ; Vol. 226, No. 5. pp. 823-835.
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Effect of additives on the preferential crystallization of L-asparagine monohydrate. / Kongsamai, Peetikamol; Maneedaeng, Atthaphon; Flood, Chalongsri; ter Horst, Joop H.; Flood, Adrian E.

In: European Physical Journal: Special Topics, Vol. 226, No. 5, 18.04.2017, p. 823-835.

Research output: Contribution to journalArticle

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AU - Flood, Adrian E.

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