Synthesis and Study of 4, 4-12-12 Alkyl Phenol Polyoxyethylene Sulfonate Gemini Surfactant

Author(s): Lu Yan*, Fan Ping.

Journal Name: Recent Innovations in Chemical Engineering
Formerly: Recent Patents on Chemical Engineering

Volume 12 , Issue 4 , 2019

Become EABM
Become Reviewer

Graphical Abstract:


Abstract:

Background: Gemini surfactants have good prospect of application development in various fields for their superior performance in foaming, wettability, and emulsification with lower critical micelle concentration (CMC) than conventional mono-surfactants.

Objective: The purpose of this study was to synthesize an ionic sulfonate Gemini surfactant, which is mainly used as an oil flooding agent, to improve oil recovery and reduce oil production cost.

Methods: With 4-dodecyl phenol, diethylene glycol and triethylene glycol as the raw materials to synthesize two sulfonate Gemini surfactants. The single factor experiment combined with Box-Behnken center composite experimental design, the optimum reaction conditions were determined. The optimal reaction condition of sulfonation was determined by orthogonal test. The product structure was characterized by nuclear magnetic resonance and infrared.

Results: The mass fraction of sodium hydroxide ω(NaOH), temperature and the quality ratio of hexadecyl trimethyl ammonium bromide to dodecyl phenol were 18%, 93.5°C and 14.2%, respectively. Under the condition of ice bath, the molar ratio of chlorosulfonic acid to 4, 4- 12-12 alkyl phenol polyoxyethylene ether was 2.02:1 and reaction for 5h. The critical micelle concentration was determined to be 2×10-4, 1.05×10-4, respectively.

Conclusion: Two sulfonate Gemini surfactants, namely 5, 5-dilauryl alkyl-2,2'-(diethylene glycol oxygen base) sodium diphenyl sulfonate and 5,5-dilauryl alkyl-2,2'-(triethylene glycol oxygen base) sodium diphenyl sulfonate (recorded as III and IV, respectively) were synthesized. The synthesized surfactants have excellent emulsification ability.

Keywords: Gemini surfactant, 4-dodecyl phenol, sulfonate, critical micelle concentration (CMC), gemini surfactant, Nuclear MR.

[1]
Qiang D, Zhang X, Gang C. Synthesis and foaming properties of new gemini anionic surfactant with multifunctional groups. Asian J Chem 2015; 27(7): 2501-4.
[http://dx.doi.org/10.14233/ajchem.2015.17955]
[2]
Sardar N, Kamil M. Kabir-ud-Din. Solution behavior of anionic polymer sodium carboxymethylcellulose (NaCMC) in presence of cationic gemini/conventional surfactants. Colloids Surf A Physicochem Eng Asp 2012; 415: 413-20.
[http://dx.doi.org/10.1016/j.colsurfa.2012.09.017]
[3]
Khan F, Siddiqui US, Khan IA, et al. Physicochemical study of cationic gemini surfactant butanediyl-1,4-bis(dimethyldodecylammonium bromide) with various counter ions in aqueous solution. Colloids Surf A Physicochem Eng Asp 2012; 394(1): 46-56.
[http://dx.doi.org/10.1016/j.colsurfa.2011.11.024]
[4]
Mirgorodskaya AB, Yackevich EI, Lukashenko SS, et al. Solubilization and catalytic behavior of micellar system based on gemini surfactant with hydroxyalkylated head group. J Mol Liq 2012; 169(5): 106-9.
[http://dx.doi.org/10.1016/j.molliq.2012.02.012]
[5]
Abreu B, Rocha J, Fernandes RMF, Regev O, Furó I, Marques EF. Gemini surfactants as efficient dispersants of multi walled carbon nanotubes: Interplay of molecular parameters on nanotube dispersibility and debundling. J Colloid Interface Sci 2019; 547(547): 69-77. [J].
[http://dx.doi.org/ [http://10.1016/j.jcis.2019.03.082] [PMID: 30939346]
[6]
Qiao M, Chen J, Yu C, et al. Gemini surfactants as novel air entraining agents for concrete. Cement Concr Res 2017; 10(100): 40-6.
[http://dx.doi.org/10.1016/j.cemconres.2017.05.019]
[7]
Srivastava A, Thapa U, Saha M, et al. Aggregation behaviour of tetracaine hydrochloride with gemini surfactants and the formation of silver nanoparticles using Drug-Gemini surfactants mixture. J Mol Liq 2019; 15(276): 399-408.
[http://dx.doi.org/10.1016/j.molliq.2018.12.006]
[8]
Akram M, Ansari F, Bhat IA, et al. Probing interaction of bovine serum albumin (BSA) with the biodegradable version of cationic gemini surfactants. J Mol Liq 2019; 15(276): 519-28.
[http://dx.doi.org/10.1016/j.molliq.2018.10.123]
[9]
Migahed MA, Hegazy MA, Al-Sabagh AM. Synergistic inhibition effect between Cu2+ and cationic gemini surfactant on the corrosion of downhole tubing steel during secondary oil recovery of old wells. Corros Sci 2012; 8(61): 10-8.
[http://dx.doi.org/10.1016/j.corsci.2012.04.004]
[10]
Migahed MA, Elgendy AM. EL-Rabiei MM, et al.Novel gemini cationic surfactants as anti-corrosion for X-65 steel dissolution in oilfield produced water under sweet conditions: Combined experimental and computational investigations. J Mol Struct 2018; 5(1159): 10-22.
[http://dx.doi.org/10.1016/j.molstruc.2018.01.033]
[11]
Heakal FE-T, Elkholy AE. Gemini surfactants as corrosion inhibitors for carbon steel. J Mol Liq 2017; 3(230): 395-407.
[http://dx.doi.org/10.1016/j.molliq.2017.01.047]
[12]
Pal N, Saxena N, Mandal A, et al. Characterization of alkali-surfactant-polymer slugs using synthesized gemini surfactant for potential application in enhanced oil recovery. J Petrol Sci Eng 2018; 9(168): 283-300.
[http://dx.doi.org/10.1016/j.petrol.2018.05.026]
[13]
Zhou H, Liang Y, Huang P, et al. Systematic investigation of ionic liquid-type gemini surfactants and their abnormal salt effects on the interfacial tension of a water/model oil system. J Mol Liq 2018; 1(249): 33-9.
[http://dx.doi.org/10.1016/j.molliq.2017.11.004]
[14]
Feng H, Hou J, Ma T, et al. The ultra-low interfacial tension behavior of the combined cationic/anionic-nonionic gemini surfactants system for chemical flooding. Colloids Surf A Physicochem Eng Asp 2018; 5(554): 74-80.
[http://dx.doi.org/10.1016/j.colsurfa.2018.06.028]
[15]
Pal N, Saxena N, Mandal A. Equilibrium and dynamic adsorption of gemini surfactants with different spacer lengths at oil/aqueous interfaces. Colloids Surf A Physicochem Eng Asp 2017; 20(533): 20-2.
[http://dx.doi.org/10.1016/j.colsurfa.2017.08.020]
[16]
Hegazy MA, El-Tabei AS, Bedair AH, et al. Synthesis and inhibitive performance of novel cationic and gemini surfactants on carbon steel corrosion in 0.5 M H2SO4 solution. RSC Advances 2015; 5(79): 64633-6465.
[http://dx.doi.org/10.1039/C5RA06473B]
[17]
Yu H, Qiang D, Yang N, et al. Synthesis and properties of a new multifunctional gemini anionic surfactant. J Chem Soc Pak 2016; 38(2): 186-91.
[18]
Panda M. Kabir-ud-Din. Study of surface and solution properties of gemini-conventional surfactant mixtures and their effects on solubilization of polycyclic aromatic hydrocarbons. J Mol Liq 2011; 163(2): 93-8.
[http://dx.doi.org/10.1016/j.molliq.2011.08.002]
[19]
Yang F, Li G, Qi J, et al. Synthesis and surface activity properties of alkylphenol polyoxyethylene nonionic trimeric surfactants. Appl Surf Sci 2010; 257(1): 312-8.
[http://dx.doi.org/10.1016/j.apsusc.2010.06.094]
[20]
Patel R, Mir MUH, Singh UK, Beg I, Islam A, Khan AB. Refolding of urea denatured cytochrome c: Role of hydrophobic tail of the cationic gemini surfactants. J Colloid Interface Sci 2016; 484(15): 205-12.
[http://dx.doi.org/10.1016/j.jcis.2016.09.004] [PMID: 27614044]
[21]
Qiu LG, Xie AJ, Shen YH. A novel triazole-based cationic gemini surfactant: Synthesis and effect on corrosion inhibition of carbon steel in hydrochloric acid. Mater Chem Phys 2005; 91(2-3): 269-73.
[http://dx.doi.org/10.1016/j.matchemphys.2004.11.022]
[22]
Chang H, Cui Y, Wang Y, et al. Wettability and adsorption of PTFE and paraffin surfaces by aqueous solutions of biquaternary ammonium salt gemini surfactants with hydroxyl. Colloids Surf A Physicochem Eng Asp 2016; 506(5): 416-24.
[http://dx.doi.org/10.1016/j.colsurfa.2016.07.012]
[23]
Chang H, Cui Y, Wei W, et al. Adsorption behavior and wettability by gemini surfactants with ester bond at polymer-solution-air systems. J Mol Liq 2017; 230(3): 429-36.
[http://dx.doi.org/10.1016/j.molliq.2017.01.056]
[24]
Li M, Zhang C, Yang X. Gemini surfactants templated mesoporous silica microparticles: From solid to hollow mesoporous spheres. Chin J Chem 2017; 35(11): 1706-10.
[http://dx.doi.org/10.1002/cjoc.201700277]
[25]
Zhi- ping LI, Rosen MJ. Two- phase mixed indicator titration method for the determination of anionic surfactants. Anal Chem 1981; 53(9): 1516-9.
[http://dx.doi.org/10.1021/ac00232a050]
[26]
Zhao X, Qi S, Wang Y, et al. Synthesis and properties of sulfonate gemini surfactants with branched hydrophobic chain. Oilfield Chem 2011; 28(3): 267-70.
[27]
Zhao G. Physical Chemistry of Surfactants. In:Beijing University Press 1991.


Rights & PermissionsPrintExport Cite as

Article Details

VOLUME: 12
ISSUE: 4
Year: 2019
Page: [262 - 274]
Pages: 13
DOI: 10.2174/2405520412666190723112325
Price: $58

Article Metrics

PDF: 11
HTML: 2
EPUB: 1
PRC: 1