Literature DB >> 26379471

The magic of aqueous solutions of ionic liquids: ionic liquids as a powerful class of catanionic hydrotropes.

Ana Filipa M Cláudio1, Márcia C Neves1, Karina Shimizu2, José N Canongia Lopes2, Mara G Freire1, João A P Coutinho1.   

Abstract

Hydrotropes are compounds able to enhance the solubility of hydrophobic substances in aqueous media and therefore are widely used in the formulation of drugs, cleaning and personal care products. In this work, it is shown that ionic liquids are a new class of powerful catanionic hydrotropes where both the cation and the anion synergistically contribute to increase the solubility of biomolecules in water. The effects of the ionic liquid chemical structures, their concentration and the temperature on the solubility of two model biomolecules, vanillin and gallic acid were evaluated and compared with the performance of conventional hydrotropes. The solubility of these two biomolecules was studied in the entire composition range, from pure water to pure ionic liquids, and an increase in the solubility of up to 40-fold was observed, confirming the potential of ionic liquids to act as hydrotropes. Using dynamic light scattering, NMR and molecular dynamics simulations, it was possible to infer that the enhanced solubility of the biomolecule in the IL aqueous solutions is related to the formation of ionic-liquid-biomolecules aggregates. Finally, it was demonstrated that hydrotropy induced by ionic liquids can be used to recover solutes from aqueous media by precipitation, simply by using water as an anti-solvent. The results reported here have a significant impact on the understanding of the role of ionic liquid aqueous solutions in the extraction of value-added compounds from biomass as well as in the design of novel processes for their recovery from aqueous media.

Entities:  

Year:  2015        PMID: 26379471      PMCID: PMC4568318          DOI: 10.1039/C5GC00712G

Source DB:  PubMed          Journal:  Green Chem        ISSN: 1463-9262            Impact factor:   10.182


  29 in total

1.  Chameleonic behavior of ionic liquids and its impact on the estimation of solubility parameters.

Authors:  Marta L S Batista; Catarina M S S Neves; Pedro J Carvalho; Rafiqul Gani; João A P Coutinho
Journal:  J Phys Chem B       Date:  2011-10-18       Impact factor: 2.991

2.  Environmental risk assessment of hydrotropes in the United States, Europe, and Australia.

Authors:  Kathleen Stanton; Caritas Tibazarwa; Hans Certa; William Greggs; Donna Hillebold; Lela Jovanovich; Daniel Woltering; Richard Sedlak
Journal:  Integr Environ Assess Manag       Date:  2010-01       Impact factor: 2.992

3.  Biocatalysis in ionic liquids.

Authors:  Fred van Rantwijk; Roger A Sheldon
Journal:  Chem Rev       Date:  2007-06       Impact factor: 60.622

4.  The structure of aqueous solutions of a hydrophilic ionic liquid: the full concentration range of 1-ethyl-3-methylimidazolium ethylsulfate and water.

Authors:  Carlos E S Bernardes; Manuel E Minas da Piedade; José N Canongia Lopes
Journal:  J Phys Chem B       Date:  2011-02-15       Impact factor: 2.991

5.  Mechanistic studies on hydrotropic solubilization of nifedipine in nicotinamide solution.

Authors:  H Suzuki; H Sunada
Journal:  Chem Pharm Bull (Tokyo)       Date:  1998-01       Impact factor: 1.645

6.  Mechanism of hydrophobic drug solubilization by small molecule hydrotropes.

Authors:  Jonathan J Booth; Steven Abbott; Seishi Shimizu
Journal:  J Phys Chem B       Date:  2012-12-13       Impact factor: 2.991

7.  Effects of structure variation on solution properties of hydrotropes: phenyl versus cyclohexyl chain tips.

Authors:  Marios Hopkins Hatzopoulos; Julian Eastoe; Peter J Dowding; Isabelle Grillo; Bruno Demé; Sarah E Rogers; Richard Heenan; Robert Dyer
Journal:  Langmuir       Date:  2012-06-06       Impact factor: 3.882

8.  Triterpenic and other lipophilic components from industrial cork byproducts.

Authors:  Andreia F Sousa; Paula C R O Pinto; Armando J D Silvestre; Carlos Pascoal Neto
Journal:  J Agric Food Chem       Date:  2006-09-06       Impact factor: 5.279

9.  Hydrotropic solubilization of paclitaxel: analysis of chemical structures for hydrotropic property.

Authors:  Jaehwi Lee; Sang Cheon Lee; Ghanashyam Acharya; Ching-jer Chang; Kinam Park
Journal:  Pharm Res       Date:  2003-07       Impact factor: 4.200

10.  Liquid clathrate formation in ionic liquid-aromatic mixtures.

Authors:  John D Holbrey; W Matthew Reichert; Mark Nieuwenhuyzen; Oonagh Sheppard; Christopher Hardacre; Robin D Rogers
Journal:  Chem Commun (Camb)       Date:  2003-02-21       Impact factor: 6.222

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  24 in total

1.  Comparing deep eutectic solvents and cyclodextrin complexes as curcumin vehicles for blue-light antimicrobial photodynamic therapy approaches.

Authors:  Eduardo Silva; Ivo M Aroso; Joana M Silva; Rui L Reis
Journal:  Photochem Photobiol Sci       Date:  2022-04-02       Impact factor: 4.328

Review 2.  Extraction and recovery processes for cynaropicrin from Cynara cardunculus L. using aqueous solutions of surface-active ionic liquids.

Authors:  Emanuelle L P de Faria; Melissa V Gomes; Ana Filipa M Cláudio; Carmen S R Freire; Armando J D Silvestre; Mara G Freire
Journal:  Biophys Rev       Date:  2018-01-02

3.  Aqueous solutions of surface-active ionic liquids: remarkable alternative solvents to improve the solubility of triterpenic acids and their extraction from biomass.

Authors:  Emanuelle L P de Faria; Selesa V Shabudin; Ana Filipa M Claúdio; Mónica Válega; Fernando M J Domingues; Carmen S R Freire; Armando J D Silvestre; Mara G Freire
Journal:  ACS Sustain Chem Eng       Date:  2017-07-11       Impact factor: 8.198

4.  Evaluation of the effect of ionic liquids as adjuvants in polymer-based aqueous biphasic systems using biomolecules as molecular probes.

Authors:  Rita de Cássia S Sousa; Matheus M Pereira; Mara G Freire; João A P Coutinho
Journal:  Sep Purif Technol       Date:  2017-07-14       Impact factor: 7.312

5.  Removal of Non-Steroidal Anti-Inflammatory Drugs from Aqueous Environments with Reusable Ionic-Liquid-based Systems.

Authors:  Hugo F D Almeida; Isabel M Marrucho; Mara G Freire
Journal:  ACS Sustain Chem Eng       Date:  2017-01-11       Impact factor: 8.198

6.  Valorization of olive tree leaves: Extraction of oleanolic acid using aqueous solutions of surface-active ionic liquids.

Authors:  Ana Filipa M Cláudio; Alice Cognigni; Emanuelle L P de Faria; Armando J D Silvestre; Ronald Zirbs; Mara G Freire; Katharina Bica
Journal:  Sep Purif Technol       Date:  2018-04-16       Impact factor: 7.312

7.  Simultaneous extraction and concentration of water pollution tracers using ionic-liquid-based systems.

Authors:  Teresa B V Dinis; Helena Passos; Diana L D Lima; Ana C A Sousa; João A P Coutinho; Valdemar I Esteves; Mara G Freire
Journal:  J Chromatogr A       Date:  2017-07-29       Impact factor: 4.759

8.  Mechanisms ruling the partition of solutes in ionic-liquid-based aqueous biphasic systems - the multiple effects of ionic liquids.

Authors:  Helena Passos; Teresa B V Dinis; Emanuel V Capela; Maria V Quental; Joana Gomes; Judite Resende; Pedro P Madeira; Mara G Freire; João A P Coutinho
Journal:  Phys Chem Chem Phys       Date:  2018-03-28       Impact factor: 3.676

Review 9.  Ionic-Liquid-Mediated Extraction and Separation Processes for Bioactive Compounds: Past, Present, and Future Trends.

Authors:  Sónia P M Ventura; Francisca A E Silva; Maria V Quental; Dibyendu Mondal; Mara G Freire; João A P Coutinho
Journal:  Chem Rev       Date:  2017-02-02       Impact factor: 60.622

10.  Ionic liquids in chromatographic and electrophoretic techniques: toward additional improvements in the separation of natural compounds.

Authors:  Belinda Soares; Helena Passos; Carmen S R Freire; João A P Coutinho; Armando J D Silvestre; Mara G Freire
Journal:  Green Chem       Date:  2016-09-07       Impact factor: 10.182

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