Biodegradable, non-bactericidal oxygen-functionalised imidazolium esters: A step towards ‘greener’ ionic liquids

Morrissey, Saibh; Pégot, Bruce; Coleman, Deborah; Garcı́a, M. Teresa; Ferguson, Damien; Quilty, Bríd; Gathergood, Nicholas

doi:10.1039/b812809j

Cited by 152 publications

(128 citation statements)

References 46 publications

(67 reference statements)

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“…biodegradable ionic liquids [15] and significantly reduces the toxicity compared with alkyl ester derivatives. Harjani et al [16,17] and Stasiewicz et al [18] also observed an increased biodegradability of pyridinium-based ionic liquids by the inclusion of oxygen-containing polar groups (ester side chain moiety, [16,17] alcohols, [18] ether groups [18] ) in the cation or by changing the anion of the ionic liquid (acesulfamates, saccharinates).…”

Section: Introductionmentioning

confidence: 99%

The Presence of Functional Groups Key for Biodegradation in Ionic Liquids: Effect on Gas Solubility

Deng¹,

Morrissey²,

Gathergood³

et al. 2010

ChemSusChem

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The effect of the incorporation of either ester or ester and ether functions into the side chain of an 1-alkyl-3-methylimidazolium cation on the physico-chemical properties of ionic liquids containing bis(trifluoromethylsulfonyl)imide or octylsulfate anions is studied. It is believed that the introduction of an ester function into the cation of the ionic liquids greatly increases their biodegradability. The density of three such ionic liquids is measured as a function of temperature, and the solubility of four gases-carbon dioxide, ethane, methane, and hydrogen-is determined between 303 K and 343 K and at pressures close to atmospheric level. Carbon dioxide is the most soluble gas, followed by ethane and methane; the mole fraction solubilities vary from 1.8 x 10(-3) to 3.7 x 10(-2). These solubilities are of the same order of magnitude as those determined for alkylimidazolium-based ionic liquids. The chemical modification of the alkyl side chain does not result in a significant change of the solvation properties of the ionic liquid. All of the solubilities decrease with increasing temperature, corresponding to an exothermal solvation process. From the variation of this property with temperature, the thermodynamic functions of solvation (Gibbs energy, enthalpy, and entropy) are calculated and provide information about the solute-solvent interactions and the molecular structure of the solutions.

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Section: Introductionmentioning

confidence: 99%

The Presence of Functional Groups Key for Biodegradation in Ionic Liquids: Effect on Gas Solubility

Deng¹,

Morrissey²,

Gathergood³

et al. 2010

ChemSusChem

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“…Auch für eine Reihe von Alkoxy-, Ester-, und Etherverbindungen [16,19,20,23,27,33] konnte eine deutlich verbesserte biologische Abbaubarkeit in unterschiedlichen Tests zur raschen biologischen Abbaubarkeit nachgewiesen werden; aber auch hier deuten die Ergebnisse darauf hin, dass die Imidazolium-Grundstruktur selbst nicht biologisch abbaubar ist.…”

Section: Imidazolium-verbindungenunclassified

Biodegradability of Ionic Liquids – Test Procedures and Structural Design

Stolte

Arning

Thöming

2011

Chemie Ingenieur Technik

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Biodegradability of Ionic Liquids -Test Procedures and Structural DesignBiotic and the abiotic degradabilities of organic chemicals are largely influenced by the potential exposure of substances to organisms and, hence, are key parameters in risk assessment for predicting spatio-temporal environmental concentrations and long-term adverse effects. Degradability in particular could be a bottleneck in designing inherently safer and sustainable ILs, because the tendency of certain ILs to be thermally and chemically very stable is often reflected by their great vis-à-vis biological degradation processes. The following review article will provide an introduction to biodegradation test procedures and will present an overview of existing aerobic and anaerobic IL biodegradation data. The discussion of this data should help to improve the future design of inherently safer ILs, thereby reducing the risks they may pose to humans and the environment.

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“…On the other hand, the toxicity of ILs increases dramatically with the increase in the length of side chain. Additionally, it was found that the incorporation of ether groups into the ester side-chain significantly reduced the toxicity compared with alkyl ester derivatives (Morrissey et al, 2009). Hence, bulky cholinium, phosphonium or ammonium based ILs with the shorter side chains on the cation core would be safer/more useful ILs for pharmaceutical use.…”

Section: Toxicity and Biodegradability Of Ilsmentioning

confidence: 99%

Ionic Liquids: Future Solvents and Reagents for Pharmaceuticals

Moniruzzaman

Goto

2011

J. Chem. Eng. Japan / JCEJ

108

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IntroductionRoom temperature ionic liquids (RTILs), an interesting class of tunable and designer solvents with the extremely low vapor pressure have been extensively used as a potential replacement for toxic, hazardous, flammable and highly volatile organic solvents (VOSs) (Welton, 1999;Rogers and Seddon, 2002 Figure 1)), and are liquids at ambient or far below ambient temperatures. In fact, the asymmetry of the cation is believed to be responsible for the low melting temperatures. Based on the solubility of ILs in water, ILs can be divided into two categories: hydrophobic (water immiscible) and hydrophilic (water miscible). This water miscibility generally depends on the anions of ILs. ILs have many attractive physicochemical properties such as negligible vapor pressure, multiple solvation interactions with organic and inorganic compounds (Anderson et al., 2002), excellent chemical and thermal stability (Kosmulski et al., 2004), high ionic conductivity and a wide liquid temperature ranges which draw the growing interest in both industrial and academic research laboratories. Most importantly, the properties regarded as the viscosity, hydrophobicity, density and solubility of ILs can be tuned by selecting different combinations of cations and anions, to customize ILs for specific demands. During the last decade, the interest in the ILs has increased significantly because of their potential as solvents and/or (co)solvents and/or reagents in a wide range of applications, including chemical engineering (separation, extraction and membranes) (Visser et al., 2001;Anderson and Armstrong, 2005)

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Biodegradable, non-bactericidal oxygen-functionalised imidazolium esters: A step towards ‘greener’ ionic liquids

Cited by 152 publications

References 46 publications

The Presence of Functional Groups Key for Biodegradation in Ionic Liquids: Effect on Gas Solubility

The Presence of Functional Groups Key for Biodegradation in Ionic Liquids: Effect on Gas Solubility

Biodegradability of Ionic Liquids – Test Procedures and Structural Design

Ionic Liquids: Future Solvents and Reagents for Pharmaceuticals

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