Phosphonium ionic liquids: design, synthesis and evaluation of biodegradability

Abstract

The biodegradability of a range of phosphonium ionic liquids (ILs) was assessed using the CO 2 headspace test (ISO 14593). Tetraalkylphosphonium cations in which one of the alkyl substituents contained ester, ether, alcohol or alkene functionality in order to promote biodegradation were targeted. These cations were paired with halide, triflimide and octylsulfate anions. In contrast to previously studied dialkylimidazolium and alkylpridinium ILs with incorporated ester moieties and octylsulfate anions, the phosphonium ILs showed relatively low levels of biodegradability. 902 496 8104; Tel: +1 902 496 8189 † Electronic supplementary information (ESI) available: 1 H, 13 C and 31 P NMR spectra of all novel phosphonium ionic liquids. See d P (121 MHz; DMSO d 6 ; 85% H 3 PO 4 ) 33.3; m/z (ESI, +ve) 327.3179 [(M-Br -) + requires 327.3175].This journal is

Persistence of selected ammonium- and phosphonium-based ionic liquids in urban park soil microcosms

“…The two other ILs (i.e., tributyl-methylammonium methanesulphonate and butyltrimethylammonium methanesulphonate) reached 7 and 4%, respectively. In a CO 2 headspace test, also Atefi et al (2009) showed that ultimate biodegradation of various tri-n-hexylphosphoniumbased ILs in an aqueous medium after 28 days ranged from 0 to 30%, depending on the side chain functionality.…”

Removal of Zn(II) from chloride acidic solutions with hydrophobic quaternary salts

“…It is the anion that influences the hydrophobicity of ILs. Most of ionic liquids containing a chloride anion are miscible in water, while those comprising PF 6 -or N(CF 3 SO 2 ) 2 -are highly hydrophobic. A great advantage of ILs is their easiness to replace the anion that makes it possible to design compounds with required properties, suited to the particular system 5,6 .…”

“…Most of ionic liquids containing a chloride anion are miscible in water, while those comprising PF 6 -or N(CF 3 SO 2 ) 2 -are highly hydrophobic. A great advantage of ILs is their easiness to replace the anion that makes it possible to design compounds with required properties, suited to the particular system 5,6 . It is the aim of this work to study the equilibrium of zinc(II) extraction from hydrochloric acid solutions with phosphonium and ammonium quaternary salts, and to apply them as carriers in polymer inclusion membranes.…”

Biodegradability of Ionic Liquids – Test Procedures and Structural Design

“…8) [15,39]. Weder für Alkyl-noch für funktionalisierte Alkoxycarbonylmethyl-Verbindungen wurde ein signifikanter biologischer Abbau beobachtet.…”