Design rules for environmental biodegradability of phenylalanine alkyl ester linked ionic liquids

Abstract

In this study, the impact of the length of the alkyl chain and cationic head group on the environmental biodegradability of l-phenylalanine ester derived ILs was systematically studied.

Toward the Proactive Design of Sustainable Chemicals: Ionic Liquids as a Prime Example

“…A substructure recurring in all compounds l -phenylalanineesterified with C2–C8 and C12 and C14 alkyl chains was fully mineralizable without formation of stable transformation products. The shortest of the homologues (C2, C4) was readily biodegradable . A comparison of biodegradability was made between imidazoliums, pyridiniums, and cholines substituted with two amino acids: phenylalanine and tyrosine.…”

“…tertiary amine, proline, dimethylaminopyridine, morpholine) connected to the amino acid moiety through amide bonds. 62,271,317 Varying levels of degradability were observed within the standard ready biodegradability test (20−63%). A pyridinium substituted L-phenylalanine IL only passed the ready biodegradability threshold, i.e.…”

“…The shortest of the homologues (C2, C4) was readily biodegradable. 317 A comparison of biodegradability was made between imidazoliums, pyridiniums, and cholines substituted with two amino acids: phenylalanine and tyrosine. These two amino acids differ from each other by the presence of a hydroxyl group; a structural element that usually increases biodegradability.…”

Mixed Oxime-Functionalized IL/16-s-16 Gemini Surfactants System: Physicochemical Study and Structural Transitions in the Presence of Promethazine as a Potential Chiral Pollutant

“…Introducing an amide group in lieu of an ester group increases the stability of the functionalized ILs toward abiotic hydrolysis and thus extends the range of conditions of their practical application. A versatile approach included introducing an amino acid moiety to link the head group and side chain in the cation of IL/surface-active IL (SAIL) [19,22], which opened an opportunity to develop SAILs with optimized environmental toxicity [23], self-assembly [24] and biodegradability [25] properties. We recently reported the synthesis and study of a series of inherently biodegradable oxime-functionalized ILs [26] proposed as a base for a green decontamination IL-surfactant system.…”

“…The gemini surfactants consist of two hydrophilic head groups and two hydrophobic chains covalently connected through a spacer group [32][33][34]. They have generated much interest because of their outstanding properties and their diverse applications compared with single-chain surfactants [25,26]. The aggregation behavior of monomeric conventional surfactants is mainly driven by intermolecular interactions, whereas a gemini surfactant is controlled by both inter-molecular and intra-molecular interactions.…”