Sweet success: ionic liquids derived from non-nutritive sweetenersElectronic supplementary information (ESI) available: experimental details; IR spectra. See http://www.rsc.org/suppdata/cc/b3/b313068a/

Carter, Elke B.; Culver, Stephanie L.; Fox, Phillip A.; Goode, Russell D.; Ntai, Ioanna; Tickell, Morgan D.; Traylor, Rachel K.; Hoffman, Neil E.; Davis, James H.

doi:10.1039/b313068a

Cited by 152 publications

(15 citation statements)

References 6 publications

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“…Melting and glass transition temperatures: Several studies [48][49][50] assumed that the introduction of carboxylic acid groups to ionic liquids would readily produce strong hydrogen bonds, and thus result in high melting points (T m ) or glass transition temperatures (T g ), so it was not appropriate for carboxylic acid groups to be incorporated into the ions. The fact is that all ten NAILs are obtained with the T m or T g below 100 8C, and six of them (shown in Table 2) are liquid at room temperature.…”

Section: Anionsmentioning

confidence: 99%

Biodegradable Naphthenic Acid Ionic Liquids: Synthesis, Characterization, and Quantitative Structure–Biodegradation Relationship

Yu¹,

Lü²,

Zhou³

et al. 2008

Chemistry A European J

203

152

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It has been confirmed that commonly used ionic liquids are not easily biodegradable. When ultimately disposed of or accidentally released, they would accumulate in the environment, which strongly restricts large-scale industrial applications of ionic liquids. Herein, ten biodegradable ionic liquids were prepared by a single, one-pot neutralization of choline and surrogate naphthenic acids. The structures of these naphthenic acid ionic liquids (NAILs) were characterized and confirmed by (1)H and (13)C NMR spectroscopy, IR spectroscopy, and elemental analysis, and their physical properties, such as densities, viscosities, conductivities, melting points (T(m)), glass transition points (T(g)), and the onset temperatures of decomposition (T(d)), were determined. More importantly, studies showed that these NAILs would be rapidly and completely biodegraded in aquatic environments under aerobic conditions, which would make them attractive candidates to be utilized in industrial processes. To explore the underlying mechanism involved in the NAIL biodegradation reaction and seek prediction of their biodegradability under environmental conditions, four molecular descriptors were chosen: the logarithm of the n-octanol/water partition coefficient (log P), van der Waals volume (V(vdW)), energies of the highest occupied molecular orbital (E(HOMO)), and energies of the lowest unoccupied molecular orbital (E(LUMO)). Through multiple linear regression, a general and qualified model including the biodegradation percentage for NAILs after the 28-day OECD 301D test (%B(28)) and molecular descriptors was developed. Regression analysis showed that the model was statistically significant at the 99 % confidence interval, thus indicating that the %B(28) of NAILs could be explained well by the quantum chemical descriptor E(HOMO), which might give some important clues in the discovery of biodegradable ionic liquids of other kinds.

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Section: Anionsmentioning

confidence: 99%

Biodegradable Naphthenic Acid Ionic Liquids: Synthesis, Characterization, and Quantitative Structure–Biodegradation Relationship

Yu¹,

Lü²,

Zhou³

et al. 2008

Chemistry A European J

203

152

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“…Biologically active ions have been used to develop novel ILs; however, the primary drive behind the research into these materials has been focused on the use of well-known low-toxicity ions to obtain ILs with the desired set of properties. [17,21,22] …”

Section: Introductionmentioning

confidence: 98%

Ionic Liquids as Active Pharmaceutical Ingredients

et al. 2011

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Ionic liquids (ILs) are ionic compounds that possess a melting temperature below 100 °C. Their physical and chemical properties are attractive for various applications. Several organic materials that are now classified as ionic liquids were described as far back as the mid-19th century. The search for new and different ILs has led to the progressive development and application of three generations of ILs: 1) The focus of the first generation was mainly on their unique intrinsic physical and chemical properties, such as density, viscosity, conductivity, solubility, and high thermal and chemical stability. 2) The second generation of ILs offered the potential to tune some of these physical and chemical properties, allowing the formation of "task-specific ionic liquids" which can have application as lubricants, energetic materials (in the case of selective separation and extraction processes), and as more environmentally friendly (greener) reaction solvents, among others. 3) The third and most recent generation of ILs involve active pharmaceutical ingredients (API), which are being used to produce ILs with biological activity. Herein we summarize recent developments in the area of third-generation ionic liquids that are being used as APIs, with a particular focus on efforts to overcome current hurdles encountered by APIs. We also offer some innovative solutions in new medical treatment and delivery options.

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“…It is known that the physicochemical properties of ionic liquids (ILs) can be tuned by varying the chemical nature of their counter ions. Thus, up till now, to prepare ILs with new properties, many biologically relevant molecules such as amino acids, [23,24] sugar, and sugar derivatives, [25,26] lactic acids, [27,28] have been incorporated in the form of anions into the ILs.…”

Section: Introductionmentioning

confidence: 99%

Novel Ascorbic Acid Based Ionic Liquids for the In Situ Synthesis of Quasi‐Spherical and Anisotropic Gold Nanostructures in Aqueous Medium

Dinda

Kotal

et al. 2008

Chemistry A European J

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A series of newly designed ascorbic acid based room temperature ionic liquids were successfully used to prepare quasi-spherical and anisotropic gold nanostructures in an aqueous medium at ambient temperature. The synthesis of these room temperature ionic liquids involves, first, the preparation of a 1-alkyl (such as methyl, ethyl, butyl, hexyl, octyl, and decyl) derivative of 3-methylimidazolium hydroxide followed by the neutralization of the derivatised product with ascorbic acid. These ionic liquids show significantly better thermal stability and their glass transition temperature (Tg) decreases with increasing alkyl chain length. The ascorbate counter anion of these ionic liquids acts as a reducing agent for HAuCl4 to produce metallic gold and the alkylated imidazolium counter cation acts as a capping/shape-directing agent. It has been found that the nature of the ionic liquids and the mole ratio of ionic liquid to HAuCl4 has a significant effect on the morphology of the formed gold nanostructures. If an equimolar mixture of ionic liquid and HAuCl4 is used, predominantly anisotropic gold nanostructures are formed and by varying the alkyl chain length attached to imidazolium cation of the ionic liquids, various particle morphologies can formed, such as quasispherical, raspberry-like, flakes or dendritic. A probable formation mechanism for such anisotropic gold nanostructures has been proposed, which is based on the results of some control experiments.

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Sweet success: ionic liquids derived from non-nutritive sweetenersElectronic supplementary information (ESI) available: experimental details; IR spectra. See http://www.rsc.org/suppdata/cc/b3/b313068a/

Abstract: The anions of the sweeteners saccharin and acesulfame form ionic liquids when paired with a variety of organic cations.

Cited by 152 publications

References 6 publications

Biodegradable Naphthenic Acid Ionic Liquids: Synthesis, Characterization, and Quantitative Structure–Biodegradation Relationship

Biodegradable Naphthenic Acid Ionic Liquids: Synthesis, Characterization, and Quantitative Structure–Biodegradation Relationship

Ionic Liquids as Active Pharmaceutical Ingredients

Novel Ascorbic Acid Based Ionic Liquids for the In Situ Synthesis of Quasi‐Spherical and Anisotropic Gold Nanostructures in Aqueous Medium

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