Combustible ionic liquids by design: is laboratory safety another ionic liquid myth?

Śmiglak, Marcin; Reichert, W. Matthew; Holbrey, John D.; Wilkes, John S.; Sun, Luyi; Thrasher, Joseph S.; Kirichenko, Kostyantyn; Singh, Shailendra P.; Katritzky, Alan R.; Rogers, Robin D.

doi:10.1039/b602086k

Cited by 321 publications

(224 citation statements)

References 14 publications

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“…ILs can present a different structural organization according the suitable combination of various organic cations and anions of organic or inorganic nature, allowing a great variety of tuneable interactions and subsequent applications, particularly in the areas of chemical, biotechnology, and pharmaceutical industry (Wasserscheid and Welton, 2002). ILs build up a unique synthetic architectural platform on which the properties of both cation and anion components can be independently modified, while retaining the essential desirable features of the IL state of matter (Smiglak et al, 2006). An IL approach has the appropriate features in the design of active pharmaceutical ingredients (APIs), where a fragile balance exists between the exact chemical functionality needed for the desired effect, in the absence of adverse side effects, and the physical properties required for manufacturing and transport, chemical stability, solubility and bioavailability (Bennett and Cole, 2003;Byrn et al, 1999).…”

Section: Introductionmentioning

confidence: 99%

Evaluation of solubility and partition properties of ampicillin-based ionic liquids

Florindo

Araújo

Alves

et al. 2013

International Journal of Pharmaceutics

102

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a b s t r a c tIn order to overcome the problems associated with low water solubility, and consequently low bioavailability of active pharmaceutical ingredients (APIs), herein we explore a modular ionic liquid synthetic strategy for improved APIs. Ionic liquids containing l-ampicillin as active pharmaceutical ingredient anion were prepared using the methodology developed in our previous work, using organic cations selected from substituted ammonium, phosphonium, pyridinium and methylimidazolium salts, with the intent of enhancing the solubility and bioavailability of l-ampicillin forms. In order to evaluate important properties of the synthesized API-ILs, the water solubility at 25 • C and 37 • C (body temperature) as well as octanol-water partition coefficients (K ow 's) and HDPC micelles partition at 25 • C were measured. Critical micelle concentrations (CMC's) in water at 25 • C and 37 • C of the pharmaceutical ionic liquids bearing cations with surfactant properties were also determined from ionic conductivity measurements.

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Section: Introductionmentioning

confidence: 99%

Evaluation of solubility and partition properties of ampicillin-based ionic liquids

Florindo

Araújo

Alves

et al. 2013

International Journal of Pharmaceutics

102

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“…ILs make a unique architectural platform on which, at least potentially, the properties of both cation and anion components can be independently modified, while retaining the core desirable features of the IL state of matter. 38 …”

Section: Ionic Liquids As Technology Enablers and Novel Materialsmentioning

confidence: 99%

Ionic Liquids Then and Now: From Solvents to Materials to Active Pharmaceutical Ingredients

Hough¹,

Rogers²

2007

Bulletin of the Chemical Society of Japan

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318

219

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Ionic liquids (ILs) have evolved from salts studied primarily for their physical properties (low melting salts which could be used as solvents) to tunable materials based upon the physical, chemical, and now even biological properties that can be introduced through either ion. In this perspective, we follow this interesting evolution with respect to our work in this growing field, and discuss possible future directions, such as the use of ILs as active pharmaceutical ingredients (APIs).

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“…6 After a reconsideration of the environmental impact of these processes, a new class of solvents, ionic liquids (ILs), has emerged in literature showing the capability of forming aqueous biphasic systems (ABS) in the presence of an inorganic salt. 7 ILs negligible volatility, 8,9 low flammability, 10 thermal stability, 11,12 and, in some cases, biocompatibility contributed to their recognition as ambientfriendly media. 13 In addition, the stability, activity, selectivity, and enantioselectivity of a particular enzyme is strongly dependent on the IL nature, and therefore, those properties can be finely tuned by correctly choosing the appropriate cation and/ or anion of the IL.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of Anion Influence on the Formation and Extraction Capacity of Ionic-Liquid-Based Aqueous Biphasic Systems

et al. 2009

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Extractive fermentation using aqueous biphasic systems (ABS) is a promising separation process since it provides a nondenaturing environment for biomolecules and improves the stability of cells. Due to environmental concerns and toxicity issues related with common volatile organic solvents, ionic liquids (ILs), a new class of nonvolatile alternative solvents, are being currently investigated for extraction purposes. In this work, a wide range of imidazolium-based ILs was studied aiming at obtaining new insights regarding their ability toward the formation of ABS and their capacity to the extraction of biomolecules. On the basis of the IL cations 1-ethyl-3-methylimidazolium and 1-butyl-3-methylimidazolium, the IL anion influence on ABS formation was assessed through their combination with chloride, bromide, acetate, hydrogensulfate, methanesulfonate, methylsulfate, ethylsulfate, trifluomethanesulfonate, trifluoroacetate, and dicyanamide. Ternary phase diagrams (and respective tie-lines) formed by these hydrophilic ILs, water, and the inorganic salt K 3 PO 4 , were measured and are reported. The results indicate that the ability of an IL to induce ABS closely follows the decrease in the hydrogen bond accepting strength or the increase in the hydrogen bond acidity of the IL anion. In addition, the extraction capacity of the studied ABS was evaluated through their application to the extraction of an essential amino acid, L-tryptophan. It is shown that the partition coefficients obtained between the IL and the K 3 PO 4 -aqueous rich phases were substantially larger than those typically obtained with polymers-inorganic salts or polymers-polysaccharides aqueous systems.

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Combustible ionic liquids by design: is laboratory safety another ionic liquid myth?

Cited by 321 publications

References 14 publications

Evaluation of solubility and partition properties of ampicillin-based ionic liquids

Evaluation of solubility and partition properties of ampicillin-based ionic liquids

Ionic Liquids Then and Now: From Solvents to Materials to Active Pharmaceutical Ingredients

Evaluation of Anion Influence on the Formation and Extraction Capacity of Ionic-Liquid-Based Aqueous Biphasic Systems

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