Synthesis of Sulfobetaine‐Type Zwitterionic Gemini Surfactants (EAPMAC) and Their Oilfield Application Properties

Abstract

Four sulfobetaine‐type zwitterionic gemini surfactants bis{[(N‐ethyl‐N alkylamide‐ethyl‐N‐(2‐hydr oxyl‐3‐sodium sulfonic acid) propyl] methylene} ammonium chlorides (EAPMAC‐11, EAPMAC‐13 EAPMAC‐15, and EAPMAC‐17) were synthesized by three steps using triethylene tetramine, fatty‐acid methyl esters, ethyl chloride, N,N′‐dimethyl ethylenediamine, and 3‐chloro‐2‐hydroxypropane sulfonic acid sodium as main raw materials. Their chemical structure was confirmed using Fourier transform infrared spectroscopy (FTIR), 1H‐Nuclear Magnetic Resonance (1H NMR), and elemental analysis. The surface activity, critical micelle concentration, and interfacial activity were correlated with the length of the carbon chain. The results show low emulsifying tendency toward crude oil, low interfical tension, high salt tolerance, and excellent long‐term thermal stability. Moreover, high biocidal activities and good protection of metal surfaces against acidic environments are also reflected. These properties suggest that these new gemini surfactants have enormous application potential in oilfield application areas.

Gemini and Bicephalous Surfactants: A Review on Their Synthesis, Micelle Formation, and Uses

“…With the aim of applying the surfactants in the oilfield, Hussain et al [83] synthesized quaternary ammonium gemini surfactants with a different length of the spacer group (C8, C10, and C12), by solvent-free amidation of glycolic acid ethoxylate lauryl ether with 3-(dimethylamino)-1-propylamine. Similarly, Zhou et al synthesized gemini surfactants in three steps using triethylene tetramine, fatty-acid methyl esters, ethyl chloride, N, N -dimethyl ethylenediamine, and 3-chloro-2-hydroxypropane sulfonic acid sodium as the main raw materials to be applied in oilfields [84].…”

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

“…They have inherent applications such as commodity production, textile industry, leather finishing, synthesis of new materials, and enhanced oil recovery. [50][51][52] Nonionic geminis are mainly derived from carbohydrate compounds. In several studies, their synthesis and surface properties have been the focus.…”

“…Zwitterionic surfactants have two polar groups with different charges on the headgroups. They have inherent applications such as commodity production, textile industry, leather finishing, synthesis of new materials, and enhanced oil recovery [50–52] . Nonionic geminis are mainly derived from carbohydrate compounds.…”

Effects of inorganic metal ions on the mixture of single polyoxyethylene chain carboxylate surfactant and Gemini quaternary ammonium surfactant

“…Anionic nonionic carboxylate surfactants and Gemini quaternary ammonium surfactants all have shown excellent surface activity and excellent salt resistance in some research studies. 21,[28][29][30][31][32][33] Our research group has explored the compound properties of AE 7 C-Na and ADQ-12 in previous studies. 34 The mixed system has strong interaction and high surface activity.…”