Synthesis of three gemini betaine surfactants and their surface active properties

Zhou, Ming; Zhang, Ze; Xu, Diaoyang; Hou, Liutong; Zhao, Wenlong; Nie, Xingcheng; Zhou, Lei; Zhao, Jinzhou

doi:10.1016/j.jtice.2016.10.012

Cited by 29 publications

(20 citation statements)

References 19 publications

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“…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. Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

“…Glycolic acid ethoxylate lauryl ether (6) (average Mn~690) (10 g, 14.49 mmol) and 3-(dimethylamino)-1-propylamine (5) (2.96 g, 28.99 mmol) were refluxed for 6 h at 160 • C in a 250 mL round bottom flask using sodium fluoride (0.06 g, 1.45 mmol) as a catalyst [29]. An extra 3-(dimethylamino)-1-propylamine (2.22 g, 21.74 mmol) was introduced in order to convert all the glycolic acid into amide intermediate (4) and the reaction progressed an extra four hours. Eventually, the unreacted 3-(dimethylamino)-1-propylamine was extracted and the solid sodium fluoride was removed to acquire intermediate 4.…”

Section: Synthesis Of Gs8mentioning

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%

“…The length of the surfactant tail in gemini cationic surfactants play a significant role to identify the surface properties. For example, increasing the length of the surfactant tail (≥C14) results in lowering CMC and increasing surface tension at CMC (γ cmc ) [4,14,15]. However, a further increase in the surfactant tail leads to poor solubility in water [16].…”

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confidence: 99%

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

2019

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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.

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Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of Gs8mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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

2019

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“…Gemini surfactants have been generating increasing interest owing to their tunable molecular geometry and their excellent performance in applications. They are expected to become widely used in the 21st century (Zhou, Zhang, et al, ; Zhou, Zhao, & Hu, ).…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in the Synthesis of Sulfonate Gemini Surfactants

Zhou

Zou

2018

J Surfact & Detergents

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Sulfonated Gemini surfactants are a relatively new class of anion surfactants, composed of 2 or more sulfonated surfactant monomers connected by a spacer at or near the head groups through a covalent bond. In general, the sulfonated Gemini surfactants show better properties compared to conventional anionic surfactants including better surface activity, a lower critical micelle concentration, enhanced detergency, excellent compatibility with other surfactants, and better solubility in high ionic strength systems. This article reviews the synthesis of the sulfonated Gemini surfactants using different raw materials. Based on the existing information in the literature, new ideas are proposed for the synthesis and application of the sulfonated Gemini surfactants.

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Research Progress on the Synthesis of Different Types of Gemini Surfactants with a Functionalized Hydrophobic Moiety and Spacer

2022

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Gemini surfactants are advantageous over conventional surfactants as they find applications as antimicrobial agents, corrosion inhibitors, enhanced oil recovery, capping agents for nanoparticle synthesis, drug delivery agents, etc. This article provides a detailed overview of synthetic procedures for various types of geminis and the fundamental physicochemical parameters of these systems. This includes a discussion on the cationic geminis based on various groups such as biphenyl, amide (with/without alkane tail), binol, quaternary ammonium (with/without hydroxyl group as a spacer), morpholinium, pyridinium, amide (with/without alkane tail), ester quaternary ammonium, and imidazolium (spacer with/without hydroxyl group and thioether/ester) types. Further, it is focused on anionic geminis with carboxylate, borate, and sulfonate head groups. Zwitterionic geminis such as betaine surfactants, cocogem surfactants based on dodecylisopropylol amine and dicarboxylic acid, diester type, sulphobetaine gemini based on S‐triazine, zwitterionic hetero gemini containing ammonium and carboxylate head groups, zwitterionic gemini containing quaternary ammonium and a sulfate group, gemini containing phosphodiester anion and quaternary ammonium salt are also reviewed. Lastly, synthesis of nonionic geminis from sunflower oil, amide‐based nonionic, sulfonamide nonionic, N,N’‐diethylaminedialkyldiamide nonionic gemini, sugar‐based gemini, and nonionic gemini with sulfonate spacer have been discussed.

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Synthesis of three gemini betaine surfactants and their surface active properties

Cited by 29 publications

References 19 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

Recent Advances in the Synthesis of Sulfonate Gemini Surfactants

Research Progress on the Synthesis of Different Types of Gemini Surfactants with a Functionalized Hydrophobic Moiety and Spacer

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