Synthesis, surface/interfacial properties, and biological activity of amide-based Gemini cationic surfactants with hydroxyl in the spacer group

Wang, Yakui; Jiang, Yonghai; Geng, Tao; Ju, Hongbin; Duan, Shengfu

doi:10.1016/j.colsurfa.2018.11.061

Cited by 70 publications

(30 citation statements)

References 40 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Three quaternary ammonium gemini surfactants (GS8, GS10, and GS12) having flexible larger spacer were synthesized by treating glycolic acid ethoxylate lauryl ether (6) with 3-(dimethylamino)-1-propylamine (5) using NaF catalyst to form intermediate (4) (Scheme 1, Figure 1). The intermediate (4) was then further reacted individually with 1,8-dibromooctane, 1,10-dibromodecane, and 1,12dibromododecane to acquired GS8, GS10, and GS12, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…The 1 H NMR spectra of GS12 (Table 1, Figure 2) showed the existence of characteristic signals at δ 0.88 ppm and δ 1.25 ppm corresponding to the CH 3 and CH 2 moieties constituting hydrophobic tail. The presence of CH 3 groups connected to the quaternary ammonium [-(CH 3 ) 2 -N-(CH 2 ) 12 -N-(CH 3 ) 2 -] was evident from a singlet peak at δ 3.27 ppm [5]. The most intense peak at δ 3.65 ppm was attributed to the presence of the ethylene oxide chain (-O-CH 2 -CH 2 -O-CH 2 -CH 2 -) [31].…”

Section: Structure Confirmationmentioning

confidence: 99%

“…In the past decades, gemini cationic surfactants containing ammonium headgroup have been extensively used for multiple oilfield applications, such as anti-corrosion in oilfield wells [1], fracturing fluid [2], micellar slug [3], foam generation [4,5], collecting and dispersing the spilled crude oil [6], reservoir stimulation [7] wettability modification [8], and enhanced oil recovery [9,10]. They possess important physicochemical activities including lower critical micelle concentration (CMC), higher interface/surface properties, good solubility, compatible with carbonate rocks, high thermal stability, and unique aggregation behavior as compared to their monomeric counterpart [5,[11][12][13]].…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of Novel Ethoxylated Quaternary Ammonium Gemini Surfactants for Enhanced Oil Recovery Application

2019

View full text Add to dashboard Cite

Two aspects are always considered in the design and development of new surfactants for oilfield application. One of them is that surfactant must be sufficiently stable at reservoir temperature and the other is the solubility of the surfactant in the injection water (usually seawater) and the formation brine. Most industrially applied surfactants undergo hydrolysis at elevated temperature and the presence of reservoir ions causes surfactant precipitation. In relevance to this, a novel series of quaternary ammonium gemini surfactants with different length of spacer group (C8, C10, and C12) was synthesized and characterized using FT-IR, 13C NMR, 1H NMR, and MALDI-TOF MS. The gemini surfactants were prepared by solvent-free amidation of glycolic acid ethoxylate lauryl ether with 3-(dimethylamino)-1-propylamine followed by reaction with dibromoalkane to obtain quaternary ammonium gemini surfactants. The gemini surfactants were examined by means of surface properties and thermal stabilities. The synthesized gemini surfactants showed excellent solubility in the formation brine, seawater, and deionized water without any precipitation for up to three months at 90 °C. Thermal gravimetric data revealed that all the gemini surfactants were decomposed above 227 °C, which is higher than the oilfield temperature (≥90 °C). The decrease in critical micelle concentration (CMC) and surface tension at CMC (γcmc) was detected by enhancing spacer length in the order C8 ˃ C10 ˃ C12 which suggested that the larger the spacer, the better the surface properties. Moreover, a further decrease in CMC and γcmc was noticed by enhancing temperature (30 °C ˃ 60 °C) and salinity (deionized water ˃ seawater). The current study provides a comprehensive investigation of quaternary ammonium gemini surfactants that can be further extended potentially to use as a suitable material for oilfield application.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Structure Confirmationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of Novel Ethoxylated Quaternary Ammonium Gemini Surfactants for Enhanced Oil Recovery Application

2019

View full text Add to dashboard Cite

show abstract

“…12 Among the various classes of surfactants, the amido-amine type gemini cationic surfactants continue to receive the attention of researchers because of their high performance in industrial applications. 13 With proper structural design of gemini cationic surfactants, it is possible to achieve a high degree of control on their physicochemical properties. Increasing the length of the lipophilic tail effectively reduces the water solubility.…”

Section: Introductionmentioning

confidence: 99%

“…14,15 The presence of an amide group makes the gemini cationic surfactants biodegradable and environmentally friendly. 13 It has been proven both theoretically and experimentally that the nature of the spacer plays a key role in the physicochemical behavior of gemini surfactants. [16][17][18] The spacer could be exible (methylene units), 19 rigid (double bond or triple bond, benzene ring), 20 hydrophilic (ether linkage), 21 and hydrophobic (hydrocarbon chain).…”

Section: Introductionmentioning

confidence: 99%

Surface and thermal properties of synthesized cationic poly(ethylene oxide) gemini surfactants: the role of the spacer

et al. 2019

View full text Add to dashboard Cite

show abstract

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

View full text Add to dashboard Cite

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

show abstract

Synthesis, surface/interfacial properties, and biological activity of amide-based Gemini cationic surfactants with hydroxyl in the spacer group

Cited by 70 publications

References 40 publications

Synthesis of Novel Ethoxylated Quaternary Ammonium Gemini Surfactants for Enhanced Oil Recovery Application

Synthesis of Novel Ethoxylated Quaternary Ammonium Gemini Surfactants for Enhanced Oil Recovery Application

Surface and thermal properties of synthesized cationic poly(ethylene oxide) gemini surfactants: the role of the spacer

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

Contact Info

Product

Resources

About