Manipulation of ionic liquid anion–solute–antisolvent interactions for the purification of acetaminophen

Weber, Cameron C.; Kunov-Kruse, Andreas Jonas; Rogers, Robin D.; Myerson, Allan S.

doi:10.1039/c5cc00198f

Cited by 34 publications

(59 citation statements)

References 35 publications

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“…Meanwhile, the results also follow the trend of the solubility of ibuprofen in such ILs, suggesting that the stronger electrostatic energies between anions and ibuprofen, the higher solubility of ibuprofen. This finding clearly demonstrates that the ILs, containing [AcO] − anion, are considered to be the most promising solvents for drug dissolution, and they can also be used in drugs crystallization …”

Section: Resultsmentioning

confidence: 74%

“…They found that the strong solvation of acetaminophen in ILs was dominated by the strong HB interaction between acetaminophen and anions, while the cations played a minor role. In another study, they found that the favorable solvation of lidocaine in imidazolium‐based ILs did not only result from the HB interactions between lidocaine and anions but also from the electrostatic interactions between lidocaine and cations, which was different from conventional experimental results that the cations played a negligible role . Furthermore, Myerson et al used COSMO‐RS calculations to demonstrate that both anions and cations form the HB interactions with the drugs, which were considered as one of the main contributing factors for the favorable solubility.…”

Section: Introductionmentioning

confidence: 94%

“…Experimentally, plenty of efforts have been attempted to understand the relationship between ILs structure and the solvation mechanism of drugs in ILs for developing new ILs . It has been speculated from various experimental observations that hydrogen bond (HB) interactions between anions and drugs is the major reason for the favorable solvation of drugs in imidazolium‐based ILs . For example, Rogers et al indicated that the amphotericin B formed stronger HB interaction with acetate anion resulting in a higher solubility in ILs than that of itraconazole.…”

Section: Introductionmentioning

confidence: 99%

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How imidazolium‐based ionic liquids solubilize the poorly soluble ibuprofen? A theoretical study

Huang

Zhang

et al. 2020

AIChE Journal

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Molecular dynamics simulations were performed to study combinations of [AcO]−, [TfO]−, [BF4]−, and [PF6]− anions paired with imidazolium cations of increasing alkyl chain length to elucidate the roles of anions and cations in solvating ibuprofen. Our simulation results revealed that ionic liquids (ILs) with strong ibuprofen solvation capacity should possess strong van der Waals force from cations and strong hydrogen bond (HB) from anions. Accordingly, it was found that ILs containing anions with strong HB acceptability, such as [AcO]− anion, were the best effective solvent for ibuprofen solvation, while the longer alkyl chain in the imidazolium cations decrease the polarity, thus increasing the affinity with ibuprofen. Therefore, it was suggested that the heterocyclic structure of imidazolium cation with moderate polarity and longer alkyl chain is a promising cation candidate, whereas the anions which have a strong HB acceptability and substituents without electron withdrawing groups are beneficial. The obtained results can provide useful information for rational design and selection of new ILs to dissolve insoluble drugs.

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Section: Resultsmentioning

confidence: 74%

Section: Introductionmentioning

confidence: 94%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

How imidazolium‐based ionic liquids solubilize the poorly soluble ibuprofen? A theoretical study

Huang

Zhang

et al. 2020

AIChE Journal

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“…The use of ILs for the purification of APIs has not been widely investigated, with only ah andfulo fl iterature reports. [14][15][16][17][18][19] Smith et al investigated the solubility of ibuprofen and acetaminophen in two very similar ILs, with the only difference asubtle variation of the alkyl chain length of the imidazolium cation used. Both ILs featured the same hydrophobic and weakly interacting anion [PF 6 ] À .T he scope of the study was to investigate the potentialt ou se ILs in future crystallization processes of the two pharmaceuticals, by investigating the solubility, [14] whereas the group in al ater paper demonstrated the crystallization of acetaminophen from the IL.…”

Section: Introductionmentioning

confidence: 99%

The A Priori Design and Selection of Ionic Liquids as Solvents for Active Pharmaceutical Ingredients

Kunov-Kruse

Weber

Rogers

et al. 2017

Chemistry A European J

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Abstract:In this paper we derive a straightforward computational approach to predict the optimal ionic liquid (IL) solvent for a given compound, based on COSMO-RS calculations. These calculations were performed on 18 different active pharmaceutical ingredients (APIs) using a matrix of 240 hypothetical ILs. These results indicated that the 18 APIs could be classified into 3 distinct categories based on their relative hydrogen bond donating or accepting ability, with similar optimal IL solvent predictions within each class. Informed by these results, a family of strongly hydrogen bond donating ILs based on the Nalkylguanidinium cation were prepared and characterized. The solubility of the APIs in each of these classes was found to be qualitatively consistent with the predictions of the COSMO-RS model. The suitability of these novel guanidinium salts as crystallization solvents was demonstrated by the use of Nbutylguanidinium bis(trifluoromethanesulfonyl)imide for the purification of crude fenofibrate using dimethylsulfoxide as an antisolvent, which resulted in good yields and excellent purities. Finally, a simple descriptor based model is proposed to suggest the best IL solvent for arbitrary APIs.Introduction:

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“…[7] One of the most important factorsd etermining the properties of an ionicl iquid (IL) is the basicity of its anion. [8][9][10][11][12][13] Their basicities can to some extent be inferred from the equilibrium constant of their corresponding acids' dissociation at low concentrations in water [2,14] (pK a values) but the accuracyo fs uch deduction is limited by solvent (medium)a nd concentratione ffects. [8][9][10][11][12][13] Their basicities can to some extent be inferred from the equilibrium constant of their corresponding acids' dissociation at low concentrations in water [2,14] (pK a values) but the accuracyo fs uch deduction is limited by solvent (medium)a nd concentratione ffects.…”

Section: Introductionmentioning

confidence: 99%

On the Use of a Protic Ionic Liquid with a Novel Cation To Study Anion Basicity

Hasani

Yarger

Angell

2016

Chemistry A European J

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The need for reliable means of ordering and quantifying the Lewis basicity of anions is discussed and the currently available methods are reviewed. Concluding that there is need for a simple impurity-insensitive tool, we have sought, and here describe, a new method using NMR spectroscopy of a weak base, a substituted urea, 1,3-dimethyl-2-imidazolidinone (DMI), as it is protonated by Brønsted acids of different strengths and characters. In all cases studied the product of protonation is a liquid (hence a protic ionic liquid). NMR spectroscopy detects changes in the electronic structure of the base upon interaction with the proton donors. As the proton-donating ability, that is, acidity, increases, there is a smooth but distinct transition from a hydrogen-bonded system (with no net proton transfer) to full ionicity. The liquid state of the samples and high concentration of nitrogen atoms, despite the very low natural abundance of its preferred NMR-active isotope ((15) N), make possible the acquisition of (15) N spectra in a relatively short time. These (15) N, along with (13) C, chemical shifts of the carbonyl atom, and their relative responses to protonation of the carbonyl oxygen, can be used as a means, sensitive to anion basicity and relatively insensitive to impurities, to sort anions in order of increasing hydrogen bond basicity. The order is found to be as follows: SbF6 (-) ClO4 (-) >FSO3 (-)

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Manipulation of ionic liquid anion–solute–antisolvent interactions for the purification of acetaminophen

Cited by 34 publications

References 35 publications

How imidazolium‐based ionic liquids solubilize the poorly soluble ibuprofen? A theoretical study

How imidazolium‐based ionic liquids solubilize the poorly soluble ibuprofen? A theoretical study

The A Priori Design and Selection of Ionic Liquids as Solvents for Active Pharmaceutical Ingredients

On the Use of a Protic Ionic Liquid with a Novel Cation To Study Anion Basicity

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