Influence of Process Parameters on Extraction Equilibria for the Chiral Separation of Amines and Amino-Alcohols with a Chiral Crown Ether

M. Steensma, N.J.M. Kuipers, A.B. de Haan, Gerard Kwant

Research output: Contribution to journalArticleAcademicpeer-review

48 Citations (Scopus)

Abstract

Reactive extraction is studied as a promising chiral separation technique for commercial production scale. For chiral separation of amines and amino alcohols, a chiral crown ether was identified as a versatile enantioselective extractant. In this paper, the influence of various process conditions on the extraction performance is studied experimentally, and a predictive model is constructed based on the chemical and physical equilibria. It was found that the operational selectivity in one extraction step is mainly determined by the complexation constants between crown ether and enantiomers (which are dependent on solvent and temperature) and by the extractant concentration, whereas the distribution ratio is also strongly influenced by the pH. The model gives an excellent prediction of the operational selectivity and a good explanation for the system's responses to changes in process conditions. The model can be used as a basis for a multistage equilibrium extractor model and for conceptual process design. Under optimal process conditions, an operational selectivity >1.5 was obtained for five out of seven model compounds, with satisfying distribution ratios (D ~ 1-10).
Original languageUndefined
Pages (from-to)588-597
JournalJournal of chemical technology and biotechnology
Volume81
Issue number4
DOIs
Publication statusPublished - 2006

Keywords

  • METIS-235433
  • enantioselective extractant
  • Reactive extraction
  • Equilibria
  • amino alcohol
  • Amine
  • Chiral separation
  • IR-72192

Cite this

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title = "Influence of Process Parameters on Extraction Equilibria for the Chiral Separation of Amines and Amino-Alcohols with a Chiral Crown Ether",
abstract = "Reactive extraction is studied as a promising chiral separation technique for commercial production scale. For chiral separation of amines and amino alcohols, a chiral crown ether was identified as a versatile enantioselective extractant. In this paper, the influence of various process conditions on the extraction performance is studied experimentally, and a predictive model is constructed based on the chemical and physical equilibria. It was found that the operational selectivity in one extraction step is mainly determined by the complexation constants between crown ether and enantiomers (which are dependent on solvent and temperature) and by the extractant concentration, whereas the distribution ratio is also strongly influenced by the pH. The model gives an excellent prediction of the operational selectivity and a good explanation for the system's responses to changes in process conditions. The model can be used as a basis for a multistage equilibrium extractor model and for conceptual process design. Under optimal process conditions, an operational selectivity >1.5 was obtained for five out of seven model compounds, with satisfying distribution ratios (D ~ 1-10).",
keywords = "METIS-235433, enantioselective extractant, Reactive extraction, Equilibria, amino alcohol, Amine, Chiral separation, IR-72192",
author = "M. Steensma and N.J.M. Kuipers and {de Haan}, A.B. and Gerard Kwant",
year = "2006",
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journal = "Journal of chemical technology and biotechnology. Biotechnology",
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publisher = "Wiley-Blackwell",
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Influence of Process Parameters on Extraction Equilibria for the Chiral Separation of Amines and Amino-Alcohols with a Chiral Crown Ether. / Steensma, M.; Kuipers, N.J.M.; de Haan, A.B.; Kwant, Gerard.

In: Journal of chemical technology and biotechnology, Vol. 81, No. 4, 2006, p. 588-597.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Influence of Process Parameters on Extraction Equilibria for the Chiral Separation of Amines and Amino-Alcohols with a Chiral Crown Ether

AU - Steensma, M.

AU - Kuipers, N.J.M.

AU - de Haan, A.B.

AU - Kwant, Gerard

PY - 2006

Y1 - 2006

N2 - Reactive extraction is studied as a promising chiral separation technique for commercial production scale. For chiral separation of amines and amino alcohols, a chiral crown ether was identified as a versatile enantioselective extractant. In this paper, the influence of various process conditions on the extraction performance is studied experimentally, and a predictive model is constructed based on the chemical and physical equilibria. It was found that the operational selectivity in one extraction step is mainly determined by the complexation constants between crown ether and enantiomers (which are dependent on solvent and temperature) and by the extractant concentration, whereas the distribution ratio is also strongly influenced by the pH. The model gives an excellent prediction of the operational selectivity and a good explanation for the system's responses to changes in process conditions. The model can be used as a basis for a multistage equilibrium extractor model and for conceptual process design. Under optimal process conditions, an operational selectivity >1.5 was obtained for five out of seven model compounds, with satisfying distribution ratios (D ~ 1-10).

AB - Reactive extraction is studied as a promising chiral separation technique for commercial production scale. For chiral separation of amines and amino alcohols, a chiral crown ether was identified as a versatile enantioselective extractant. In this paper, the influence of various process conditions on the extraction performance is studied experimentally, and a predictive model is constructed based on the chemical and physical equilibria. It was found that the operational selectivity in one extraction step is mainly determined by the complexation constants between crown ether and enantiomers (which are dependent on solvent and temperature) and by the extractant concentration, whereas the distribution ratio is also strongly influenced by the pH. The model gives an excellent prediction of the operational selectivity and a good explanation for the system's responses to changes in process conditions. The model can be used as a basis for a multistage equilibrium extractor model and for conceptual process design. Under optimal process conditions, an operational selectivity >1.5 was obtained for five out of seven model compounds, with satisfying distribution ratios (D ~ 1-10).

KW - METIS-235433

KW - enantioselective extractant

KW - Reactive extraction

KW - Equilibria

KW - amino alcohol

KW - Amine

KW - Chiral separation

KW - IR-72192

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JO - Journal of chemical technology and biotechnology. Biotechnology

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