Relationship between structure and biodegradability of gemini imidazolium surface active ionic liquids

Wang, Guowei; Xu, Xiaoqing; Sun, Yu; Zhuang, Linghua; Yao, Cheng

doi:10.1016/j.molliq.2018.12.066

Cited by 16 publications

(9 citation statements)

References 63 publications

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“…The biodegradability for C m ‐E2O2‐C m gemini surfactants is far better than 12‐MOH‐O‐MOH‐12 and 18‐MOH‐O‐MOH‐18 (cationic gemini surfactants containing an O‐substituted spacer and hydroxyethyl moiety in the polar heads) (Kaczerewska et al, 2018). The biodegradation percentage (9–18%) in 28 days for the geminis [C n Bim 2 ]Br 2 ( n = 12, 14 and 16; containing imidazolium group) is quite lesser than the C m ‐E2O2‐C m gemini surfactants (in 5 days) (Wang et al, 2019b). The dimeric (PMTH2E8 and PMTH2E10) and trimeric (PMTH3E8 and PMTH3E10) geminis containing betaine ester in alkyl chains have comparatively lesser biodegradation than the C m ‐E2O2‐C m gemini surfactants (contain betaine ester in spacer), while that of PMTH3E12 is comparable to only C 16 ‐E2O2‐C 16 (Garcia et al, 2019).…”

Section: Resultsmentioning

confidence: 99%

“…The easiest route of biodegradation in the case of synthesized ester‐functionalized gemini surfactants is that microorganisms attack to the tail end of hydrophobic alkyl chain or intermediate active sites, then cleave to the hydrophobic and spacer group. The ester groups of gemini surfactants convert into fatty acid and polar intermediate due to rapid hydrolysis and finally biodegradation to CO 2 , N 2 , and H 2 O under the action of environmental microorganism enzymes (Garcia et al, 2019; Wang et al, 2019b). Henceforth, these cationic geminis are often referred to as “biodegradable gemini surfactants.”…”

Section: Resultsmentioning

confidence: 99%

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An Insight View on Synthetic Protocol, Surface Activity, and Biological Aspects of Novel Biocompatible Quaternary Ammonium Cationic Gemini Surfactants

Akram

Lal

Osama

et al. 2020

J Surfact & Detergents

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In this study, we prepared a novel series of diester-functionalized cationic gemini surfactants (C m-E2O2-C m) containing ethylene oxide as a spacer with varying alkyl chain lengths and characterized by 1 H NMR, FT-IR, elemental analysis, and ESI-MS. The physicochemical properties of the geminis were explored by tensiometry, fluorescence, dye solubilization, and Krafft point. These geminis acquire superior surface activity than the conventional surfactants. Fluorescence spectroscopy analysis affirmed that the micropolarity and aggregation number of micelles diminished with increase in the alkyl chain length. These geminis represent a new group of amphiphiles of considerably high biodegradability, better cleavability, and low toxicity as assessed by BOD test, FT-IR analysis, and HC 50 analysis, respectively. They also showed significant level of antimicrobial activity toward some specified bacterial strains of Gram-positive and Gram-negative by using agar well diffusion method. Furthermore, the thermogravimetric analysis provided information regarding thermal stabilities of the newly synthesized gemini surfactants. Keywords C m-E2O2-C m gemini surfactants Á Physicochemical properties Á Antimicrobial activities Á TGA

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

An Insight View on Synthetic Protocol, Surface Activity, and Biological Aspects of Novel Biocompatible Quaternary Ammonium Cationic Gemini Surfactants

Akram

Lal

Osama

et al. 2020

J Surfact & Detergents

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“…The filtrate was evaporated to dryness and subsequently recrystallized from deionized water to obtain 1,4-bis(1H-imidazol-1-yl)butane (6a) in 5.45 g (78% yield). To a 250 mL round bottom flask containing 60% sodium hydride dispersion in mineral oil (3.85 g, 88.14 mmol) in THF (10 mL), the solution of imidazole (4) (5.00 g, 73.45 mmol) in THF (20 mL) was slowly added at 0 • C for 1 h. 1,6-Dibromohexane (5b) (5.7 mL, 36.73 mmol) was added at room temperature, and the mixture was further refluxed for 72 h, according to published literature [56,57] as condition B. After the reaction was complete, the resulting solution was filtered to remove NaBr and washed with THF.…”

Section: Synthesis Of 1n-bis(1h-imidazol-1-yl)alkane (1n-bis[bim] 6a-6d)mentioning

confidence: 99%

“…The results suggested that the ROP of CL with compound 7a cannot occur under the synthetic condition used in this work. In 1,4-bis[Bim][Br] (7a) system, the strong H-bond between Br ion and H atom on the imidazole ring reduced its catalytic efficiency in the ROP of CL [56]. In the case of 1,4-bis[Bim][PF 6 ] catalyst (2a), the polymerization of CL was completed after 48 h at the molar ratios of CL/nBuOH/DILs of 200-700/1.0/0.25-4.0.…”

Section: Synthesis Of Poly(ε-caprolactone) Via the Rop Of ε-Caprolactone Using The Synthesized 14-bis[bim][pf 6 ] (2a) Catalyst With 1-bumentioning

confidence: 99%

Organocatalytic Ring-Opening Polymerization of ε-Caprolactone Using bis(N-(N′-butylimidazolium)alkane Dicationic Ionic Liquids as the Metal-Free Catalysts: Polymer Synthesis, Kinetics and DFT Mechanistic Study

et al. 2021

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In this work, we successfully synthesized high thermal sTable 1,n-bis(N-(N′-butylimidazolium)alkane bishexafluorophosphates (1,n-bis[Bim][PF6], n = 4, 6, 8, and 10) catalysts in 55–70% yields from imidazole which were applied as non-toxic DILs catalysts with 1-butanol as initiator for the bulk ROP of ε-caprolactone (CL) in the varied ratio of CL/nBuOH/1,4-bis[Bim][PF6] from 200/1.0/0.25‒4.0 to 700/1.0/0.25‒4.0 by mol%. The result found that the optimal ratio of CL/nBuOH/1,4-bis[Bim][PF6] 400/1.0/0.5 mol% at 120 °C for 72 h led to the polymerization conversions higher than 95%, with the molecular weight (Mw) of PCL 20,130 g mol−1 (Đ~1.80). The polymerization rate of CL increased with the decreasing linker chain length of ionic liquids. Moreover, the mechanistic study was investigated by DFT using B3LYP (6–31G(d,p)) as basis set. The most plausible mechanism included the stepwise and coordination insertion in which the alkoxide insertion step is the rate-determining step.

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“…Formation of ionogels can be exploited, e.g., in waste-water decontamination and drug delivery [ 27 , 28 ]. Equally important, however, is that the presence of these hydrolysable functional groups contributes to their aerobic biodegradation [ 29 ], an issue that is becoming important due to their increased applications, e.g., in high-temperature lubricants, for gas chromatography (stationary phases), in conductive polymer supercapacitors, and as gel polymer electrolyte for sodium-ion batteries [ 30 , 31 , 32 , 33 , 34 , 35 ].…”

Section: Introductionmentioning

confidence: 99%

Ionic Liquid-Based Surfactants: Recent Advances in Their Syntheses, Solution Properties, and Applications

et al. 2021

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The impetus for the expanding interest in ionic liquids (ILs) is their favorable properties and important applications. Ionic liquid-based surfactants (ILBSs) carry long-chain hydrophobic tails. Two or more molecules of ILBSs can be joined by covalent bonds leading, e.g., to gemini compounds (GILBSs). This review article focuses on aspects of the chemistry and applications of ILBSs and GILBSs, especially in the last ten years. Data on their adsorption at the interface and micelle formation are relevant for the applications of these surfactants. Therefore, we collected data for 152 ILBSs and 11 biamphiphilic compounds. The head ions of ILBSs are usually heterocyclic (imidazolium, pyridinium, pyrrolidinium, etc.). Most of these head-ions are also present in the reported 53 GILBSs. Where possible, we correlate the adsorption/micellar properties of the surfactants with their molecular structures, in particular, the number of carbon atoms present in the hydrocarbon “tail”. The use of ILBSs as templates for the fabrication of mesoporous nanoparticles enables better control of particle porosity and size, hence increasing their usefulness. ILs and ILBSs form thermodynamically stable water/oil and oil/water microemulsions. These were employed as templates for (radical) polymerization reactions, where the monomer is the “oil” component. The formed polymer nanoparticles can be further stabilized against aggregation by using a functionalized ILBS that is co-polymerized with the monomers. In addition to updating the literature on the subject, we hope that this review highlights the versatility and hence the potential applications of these classes of surfactants in several fields, including synthesis, catalysis, polymers, decontamination, and drug delivery.

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Relationship between structure and biodegradability of gemini imidazolium surface active ionic liquids

Cited by 16 publications

References 63 publications

An Insight View on Synthetic Protocol, Surface Activity, and Biological Aspects of Novel Biocompatible Quaternary Ammonium Cationic Gemini Surfactants

An Insight View on Synthetic Protocol, Surface Activity, and Biological Aspects of Novel Biocompatible Quaternary Ammonium Cationic Gemini Surfactants

Organocatalytic Ring-Opening Polymerization of ε-Caprolactone Using bis(N-(N′-butylimidazolium)alkane Dicationic Ionic Liquids as the Metal-Free Catalysts: Polymer Synthesis, Kinetics and DFT Mechanistic Study

Ionic Liquid-Based Surfactants: Recent Advances in Their Syntheses, Solution Properties, and Applications

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