Biodegradability and aquatic toxicity of quaternary ammonium-based gemini surfactants: Effect of the spacer on their ecological properties

Abstract

Aerobic biodegradability and aquatic toxicity of five types of quaternary ammonium-based gemini surfactants have been examined. The effect of the spacer structure and the head group polarity on the ecological properties of a series of dimeric dodecyl ammonium surfactants has been investigated. Standard tests for ready biodegradability assessment (OECD 310) were conducted for C12 alkyl chain gemini surfactants containing oxygen, nitrogen or a benzene ring in the spacer linkage and/or a hydroxyethyl group attached to the nitrogen atom of the head groups. According to the results obtained, the gemini surfactants examined cannot be considered as readily biodegradable compounds. The negligible biotransformation of the gemini surfactants under the standard biodegradation test conditions was found to be due to their toxic effects on the microbial population responsible for aerobic biodegradation. Aquatic toxicity of gemini surfactants was evaluated against Daphnia magna. The acute toxicity values to Daphnia magna, IC50 at 48 h exposure, ranged from 0.6 to 1 mg/L. On the basis of these values, the gemini surfactants tested should be classified as toxic or very toxic to the aquatic environment. However, the dimeric quaternary ammonium-based surfactants examined result to be less toxic than their corresponding monomeric analogs. Nevertheless the aquatic toxicity of these gemini surfactants can be reduced by increasing the molecule hydrophilicity by adding a heteroatom to the spacer or a hydroxyethyl group to the polar head groups.

Tandem mass spectrometric analysis of novel peptide‐modified gemini surfactants used as gene delivery vectors

“…The second product ion results from the loss of the terminal lysine amino acid residue (observed at m/z 129.10 (b 2 )) by amide bond cleavage forming a doubly charged product ion (10) at m/z 474.49. Elimination of the pipecolic acid part of ion (9) also leads to the formation of ion (10), which subsequently dissociates by eliminating the last terminal lysine, forming ion (11) observed at m/z 410.44. Furthermore, ion (10) loses the tail region and the attached head forming the previously mentioned singly and doubly charged ions designated as (4) and (4 0 ).…”

“… In fact, Badea et al reported threefold increase in topical transgene expression in animals treated with N , N ′‐bis(dimethylhexadecyl)‐1,3‐propanediammonium dibromide (designated as 16‐3‐16) gemini surfactant‐based nanoparticles compared with animals treated with naked DNA . Despite the success of the traditional gemini surfactants, concerns regarding their toxicity have arisen . Several approaches have been undertaken to address this problem, including the insertion of biocompatible and biodegradable moieties such as sugars, lipids and amino acids .…”

“…[9] Despite the success of the traditional gemini surfactants, concerns regarding their toxicity have arisen. [10] Several approaches have been undertaken to address this problem, including the insertion of biocompatible and biodegradable moieties such as sugars, lipids and amino acids. [11][12][13] For example, glycyl-lysine substituted gemini surfactants exhibited significantly higher gene expression in vitro and lower cytotoxicity compared with the unsubstituted parent compound.…”

The Role of Surfactants in Liquid Soaps and Its Antimicrobial Properties

“…Garcia et al, 2016 investigated biodegradability and aquatic toxicity of quaternary ammonium-based gemini surfactants and found that these surfactants are less toxic to the aquatic life than the monomeric ones. Furthermore, the aquatic toxicity can be reduced by increasing the hydrophilicity of the surfactant molecule by including a heteroatom in the spacer or replacing a methyl by a hydroxyethyl group in the ammonium polar head group (Garcia et al, 2016).…”

Utilization of rigid polyurethane foam waste in removal of uncontrolled releases of hazardous substances

“…An ever increasing attention is paid to problems related to post-incident waste of foaming agents. These agents, due to the surfactants contained in them, may have an adverse effect on the environment [2][3][4][5][6][7][8][9][10]. One of the solutions enabling an easy and safe removal of hazardous substances is the use of sorbents, which, depending on their bulk density, can be used both in land and water actions [11].…”