Modelling the effects of ethanol on the solubility of the proteinogenic amino acids with the NRTL, Gude and Jouyban-Acree models

Nathan A. Bowden*, David Mendez Sevillano, Johan P.M. Sanders, Marieke E. Bruins

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

2 Citations (Scopus)

Abstract

The addition of organic solvents, such as ethanol, to molecules in solution is an effective process for crystallization and is used in industrial settings (i.e. pharmaceutical production, downstream processing, etc.). In this study, we use solubility data of all proteinogenic α-amino acids in binary ethanol/water systems to model their excess solubility. We use the empirical and regressive models of Gude and NRTL and the predictive Jouyban-Acree model. Based on the results, we hypothesize that amino acids that are spherical and lack a reactive side chain show little or no excess solubility. Being rod-like and/or having a reactive side chain leads to a positive excess solubility in a mixed solvent of ethanol and water. The empirical and regressed models, NRTL and Gude, fit the data well and the predictive Jouyban-Acree model, not originally intended to be used for small molecules, is less accurate but offers insights into the thermodynamic properties of the amino acids.
Original languageEnglish
Pages (from-to)158-169
JournalFluid Phase Equilibria
Volume459
DOIs
Publication statusPublished - 15 Mar 2018

Fingerprint

amino acids
Amino acids
Ethanol
ethyl alcohol
solubility
Solubility
Amino Acids
Molecules
Water
Crystallization
Drug products
Organic solvents
water
molecules
rods
Thermodynamic properties
thermodynamic properties
crystallization
Processing
Pharmaceutical Preparations

Keywords

  • Aqueous-solutions
  • Equilibria
  • Excess solubility
  • Organic solvents
  • Thermodynamics

Cite this

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title = "Modelling the effects of ethanol on the solubility of the proteinogenic amino acids with the NRTL, Gude and Jouyban-Acree models",
abstract = "The addition of organic solvents, such as ethanol, to molecules in solution is an effective process for crystallization and is used in industrial settings (i.e. pharmaceutical production, downstream processing, etc.). In this study, we use solubility data of all proteinogenic α-amino acids in binary ethanol/water systems to model their excess solubility. We use the empirical and regressive models of Gude and NRTL and the predictive Jouyban-Acree model. Based on the results, we hypothesize that amino acids that are spherical and lack a reactive side chain show little or no excess solubility. Being rod-like and/or having a reactive side chain leads to a positive excess solubility in a mixed solvent of ethanol and water. The empirical and regressed models, NRTL and Gude, fit the data well and the predictive Jouyban-Acree model, not originally intended to be used for small molecules, is less accurate but offers insights into the thermodynamic properties of the amino acids.",
keywords = "Aqueous-solutions, Equilibria, Excess solubility, Organic solvents, Thermodynamics",
author = "Bowden, {Nathan A.} and Sevillano, {David Mendez} and Sanders, {Johan P.M.} and Bruins, {Marieke E.}",
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language = "English",
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Modelling the effects of ethanol on the solubility of the proteinogenic amino acids with the NRTL, Gude and Jouyban-Acree models. / Bowden, Nathan A.; Sevillano, David Mendez; Sanders, Johan P.M.; Bruins, Marieke E.

In: Fluid Phase Equilibria, Vol. 459, 15.03.2018, p. 158-169.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Modelling the effects of ethanol on the solubility of the proteinogenic amino acids with the NRTL, Gude and Jouyban-Acree models

AU - Bowden, Nathan A.

AU - Sevillano, David Mendez

AU - Sanders, Johan P.M.

AU - Bruins, Marieke E.

PY - 2018/3/15

Y1 - 2018/3/15

N2 - The addition of organic solvents, such as ethanol, to molecules in solution is an effective process for crystallization and is used in industrial settings (i.e. pharmaceutical production, downstream processing, etc.). In this study, we use solubility data of all proteinogenic α-amino acids in binary ethanol/water systems to model their excess solubility. We use the empirical and regressive models of Gude and NRTL and the predictive Jouyban-Acree model. Based on the results, we hypothesize that amino acids that are spherical and lack a reactive side chain show little or no excess solubility. Being rod-like and/or having a reactive side chain leads to a positive excess solubility in a mixed solvent of ethanol and water. The empirical and regressed models, NRTL and Gude, fit the data well and the predictive Jouyban-Acree model, not originally intended to be used for small molecules, is less accurate but offers insights into the thermodynamic properties of the amino acids.

AB - The addition of organic solvents, such as ethanol, to molecules in solution is an effective process for crystallization and is used in industrial settings (i.e. pharmaceutical production, downstream processing, etc.). In this study, we use solubility data of all proteinogenic α-amino acids in binary ethanol/water systems to model their excess solubility. We use the empirical and regressive models of Gude and NRTL and the predictive Jouyban-Acree model. Based on the results, we hypothesize that amino acids that are spherical and lack a reactive side chain show little or no excess solubility. Being rod-like and/or having a reactive side chain leads to a positive excess solubility in a mixed solvent of ethanol and water. The empirical and regressed models, NRTL and Gude, fit the data well and the predictive Jouyban-Acree model, not originally intended to be used for small molecules, is less accurate but offers insights into the thermodynamic properties of the amino acids.

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KW - Equilibria

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KW - Thermodynamics

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