季铵盐型双子表面活性剂及其改性黏土的研究和应用进展

doi:10.3969/j.issn.1001-1803.2021.04.012

Abstract

Abstract:

The synthesis of quaternary ammonium Gemini surfactants and their application in adsorption of organic pollutants in water by modified clay were reviewed. Starting from the synthesis of alkyl quaternary ammonium Gemini surfactants, emphasis was given on the introduction of different types of quaternary ammonium Gemini surfactants and their synthetic routes from four aspects, i.e. changing the structures of the spacer group, hydrophobic group, cationic connection point and counterion. The application of quaternary ammonium Gemini surfactants to modify different kinds of natural clay was also reviewed. Finally, based on the development background of green chemistry, the development direction of Gemini surfactants in the future and the opportunities and challenges of their application in water pollution control were discussed.

Key words: quaternary ammonium Gemini surfactant, synthesis, modified clay, organic pollutant, adsorption

CLC Number:

TQ423

FU Duo-jiao,ZHOU Yin,CHEN Han-yu,LIU Hong-qin,XU Bao-cai. Advances in research and application of quaternary ammonium Gemini surfactants and their modified clay[J].China Surfactant Detergent & Cosmetics, 2021, 51(4): 338-347.

Figures/Tables 15

Fig. 1

Fig. 2

Fig. 3

Fig. 4

Fig. 5

Fig. 6

Fig. 7

Fig. 8

Fig. 9

Fig. 10

Fig. 11

Fig. 12

Fig. 13

Fig. 14

Fig. 15

References 46

[1]	Lin Yu. The present situation and harm of water pollution in China[J]. Low Carbon World, 2018,10:9-10.
[2]	Tuchowska M, Woowiec M, Solińska A, et al. Organo-modified vermiculite: preparation, characterization, and sorption of arsenic compounds[J]. Minerals, 2019,9(8) : 483-504.
[3]	Tripathy D B, Mishra A. Convenient synjournal, characterization and surface active properties of novel cationic Gemini surfactants with carbonate linkage based on C₁₂-C₁₈ sat./unsat. fatty acids[J]. Journal of Applied Research & Technology, 2017,15(2) : 93-101.
[4]	Luo W H, Ouyang J P, Antwi P, et al. Microwave/ultrasound-assisted modification of montmorillonite by conventional and Gemini alkyl quaternary ammonium salts for adsorption of chromate and phenol: structure-function relationship[J]. Science of the Total Environment, 2019,665:1104-1112.
[5]	Zhou X Q, Hu S Q, Wang Y, et al. The surface adsorption, aggregate structure and antibacterial activity of Gemini quaternary ammonium surfactants with carboxylic counterions[J]. Royal Society Open Science, 2019,6(8) : 190378.
[6]	Wang Y K, Jiang Y J, Geng T, et al. Synjournal, surface/interfacial properties, and biological activity of amide-based Gemini cationic surfactants with hydroxyl in the spacer group[J]. Colloids and Surfaces A, 2019,563:1-10.
[7]	Zana R, Benrraou M, Rueff R. Alkanediyl-α, ω-bis(dimethylalkylammonium bromide)surfactants. 1. Effect of the spacer chain length on the critical micelle concentration and micelle ionization degree[J]. Langmuir, 1991,7(6) : 1072-1075.
[8]	Maja S, Ines P, Nada F V. Adsorption and association in aqueous solutions of dissymmetric Gemini surfactant[J]. Journal of Colloid and Interface Science, 2002,250(1) : 221-229.
[9]	Chen Ruilan, Zheng Cheng, Lin Jing, et al. Research progress and prospect of Gemini quaternary ammonium salt surfactants with ester group[J]. Chemical Industry and Engineering Progress, 2013,32(11) : 2707-2012.
[10]	Ye Zhiwen. Study on synjournal and surface activities of the Gemini surfactants C₁₂-3-C₁₂·2Br and C₁₂-3(OH)-C₁₂·2Cl[J]. Chemical Reagents, 2007,9:513-516.
[11]	Cai Ying. Intermolecular hydrogen bond of the surfactant containing polar group[J]. Detergent & Cosmetics, 2012,35(2) : 18-21.
[12]	Wettig S D, Wang C Z, Verrall R E, et al. Thermodynamic and aggregation properties of aza- and imino-substituted Gemini surfactants designed for gene delivery[J]. Physical Chemistry Chemical Physics, 2007,9(7) : 871-877.
[13]	Brycki B, Koziróg A, Iwona K, et al. Synjournal, structure, surface and antimicrobial properties of new oligomeric quaternary ammonium salts with aromatic spacers[J]. Molecules, 2017,22(11) : 1810-1828.
[14]	Tiwari A K, Sonu , Saha S K. Aggregation properties and thermodynamics of micellization of Gemini surfactants with diethyl ether spacer in water and water-organic solvent mixed media[J]. Journal of Chemical Thermodynamics, 2014,70:24-32.
[15]	Wettig S D, Nowak P, Verrall R E. Thermodynamic and aggregation properties of Gemini surfactants with hydroxyl substituted spacers in aqueous solution[J]. Langmuir, 2002,18(14) : 5354-5359.
[16]	Stjerndahl M, Holmberg K. Synjournal, stability, and biodegradability studies of a surface-active amide[J]. Journal of Surfactants and Detergents, 2005,8(4) : 331-337.
[17]	Woch J, Hordyjewicz-Baran Z, Kuliszewska E, et al. Self-organization and solubilization properties of Gemini hydrotropic compounds in aqueous solution[J]. Colloids & Surfaces A: Physicochemical & Engineering Aspects, 2016,506:264-275.
[18]	Geng Tao, Li Qiuxiao, Shui Dabo et al. Properties of stearic acid triethanolamine ester quaternary[J]. China Surfactant Detergent & Cosmetics, 2004,34(4) : 220-222.
[19]	Tehrani-Bagha A R, Oskarsson H, Ginkel C G V, et al. Cationic ester-containing Gemini surfactants: chemical hydrolysis and biodegradation[J]. Journal of Colloid & Interface Science, 2007,312(2) : 444-452. pmid: 17481647
[20]	Tehrani-Bagha A R, Holmberg K. Cationic ester-containing Gemini surfactants: physical-chemical properties[J]. Langmuir, 2010,26(12) : 9276-9282. pmid: 20387872
[21]	Li J Y, Yang P F, Sha Z L, et al. Synjournal and micellization of organosilicon Gemini quaternary ammonium surfactants[J]. Journal of Surfactants and Detergents, 2015,18(1) : 155-161.
[22]	Liu Yan, Guo Liang, Bi Kai, et al. Synjournal of cationic Gemini surfactant and its application in water blocking[J]. Fine and Specialty Chemicals, 2011,19(8) : 8-10.
[23]	Han Shiyan, Song Zhanqian, Jin Zhongling, et al. Synjournal and analysis of rosin-based quaternary ammonium Gemini surfactant[J]. Forestry Science & Technology, 2009,34(4) : 61-64.
[24]	Guo Naini, Zheng Minyan, Yang Lianli. Progress in synjournal of heterocyclic cationic Gemini surfactants[J]. Petrochemical Technology, 2019,48(8) : 871-877.
[25]	Hao Junsheng, Qin Tao, Wang Pan, et al. Synjournal and interfacial adsorption behavior of novel quinoline Gemini surfactants[J]. Fine Chemicals, 2019,36(5) : 843-849.
[26]	Cai B, Li X F, Yang Y, et al. Surface properties of Gemini surfactants with pyrrolidinium head groups[J]. J Colloid Interface Sci, 2012,370(1) : 111-116. doi: 10.1016/j.jcis.2011.12.025 pmid: 22261268
[27]	Ge Jun, Fan Guodong, Chai Lingling. Synjournal and properties of quaternary ammonium imidazoline Gemini surfactant[J]. Fine Chemicals, 2011,5(28) : 447-450.
[28]	Hao J S, Qin T, Zhang Y B, et al. Synjournal, surface properties and antimicrobial performance of novel Gemini pyridinium surfactants[J]. Colloids and surfaces B: Biointerfaces, 2019,181:814-821.
[29]	Liu H Q, Zhou X Q, Zhang X X, et al. Green synjournal, surface activity, micellar aggregation, and corrosion inhibition properties of new Gemini quaternary ammonium surfactants[J]. Journal of Chemical and Engineering Data, 2018,63:1304-1315.
[30]	Chen Cheng. Molecular dynamics simulation of interlayer structure of vermiculite[D]. Nanjing: Nanjing University, 2019.
[31]	Brigatti M F, Galán E, Theng B K G. Structure and mineralogy of clay minerals[J]. Developments in Clay Science, 2013,5:21-81.
[32]	Yang S F, Gao M L, Luo Z X. Adsorption of 2-naphthol on the organo-montmorillonites modified by Gemini surfactants with different spacers[J]. Chemical Engineering Journal, 2014,256:39-50.
[33]	Yang S F, Gao M L, Luo Z X, et al. The characterization of organo-montmorillonite modified with a novel aromatic-containing Gemini surfactant and its comparative adsorption for 2-naphthol and phenol[J]. Chemical Engineering Journal, 2015,268:125-134.
[34]	Shen T, Gao M L. Gemini surfactant modified organo-clays for removal of organic pollutants from water: a review[J]. Chemical Engineering Journal, 2019,375:121910-121937.
[35]	Taleb K, Pillin I, Grohens Y, et al. Gemini surfactant modified clays: effect of surfactant loading and spacer length[J]. Applied Clay Science, 2018,161:48-56.
[36]	Peng S Y, Mao T Y, Zheng C, et al. Polyhydroxyl Gemini surfactant-modified montmorillonite for efficient removal of methyl orange[J]. Colloids and Surfaces A, 2019,578:123602-123614.
[37]	Ji Y X, Zhong H, Chen P, et al. Single and simultaneous adsorption of methyl orange and p-chlorophenol on organo-vermiculites modified by an asymmetric Gemini surfactant[J]. Colloids and Surfaces A, 2019,580:123740-123749.
[38]	Zhang Shuai, Hua Manyu, Zhang Jian. Preparation of organic montmorillonite and study on modification of asphalt[J]. Highways &Automotive Applications, 2019,191(2) : 92-96.
[39]	Li P P, Khan M A, Xia M Z, et al. Efficient preparation and molecular dynamic(MD)simulations of Gemini surfactant modified layered montmorillonite to potentially remove emerging organic contaminants from wastewater[J]. Ceramics International, 2019,45:10782-10791.
[40]	Xu Y, Khan M A, Wang F Y, et al. Novel multi amine-containing Gemini surfactant modified montmorillonite as adsorbents for removal of phenols[J]. Applied Clay Science, 2018,162:204-213.
[41]	Shen Tao. Insights into the adsorption performances of organo-vermiculites and organo silica nanosheets[D]. Beijing: China University of Petroleum, 2018.
[42]	Wang J, Gao M L, Ding F, et al. Organo-vermiculites modified by heating and Gemini pyridinium surfactants: preparation, characterization and sulfamethoxazole adsorption[J]. Colloids and Surfaces A, 2018,546:143-152.
[43]	Cao G, Gao M, Shen T, et al. Comparison between asymmetric and symmetric Gemini surfactant-modified novel organo-vermiculites for removal of phenols[J]. Industrial & Engineering Chemistry Research, 2019,58(29) : 12927-12938.
[44]	Shen T, Gao M, Zang W, et al. Architecting organo silica nanosheets for regenerable cost-effective organics adsorbents[J]. Chemical Engineering Journal, 2017,331:211-220.
[45]	Zheng Y Y, Liu W W, Wang Q Y, et al. Study of STAB- and DDAB- modified sepiolite tructures and their adsorption performance for emulsified oil in produced water[J]. Colloid and Interface Science Communications, 2020,34:100231-100238.
[46]	Zhao S, Huang G H, Mu S, et al. Immobilization of phenanthrene onto Gemini surfactant modified sepiolite at solid/aqueous interface: equilibrium, thermodynamic and kinetic studies[J]. Science of the Total Environment, 2017,598:619-627.

Advances in research and application of quaternary ammonium Gemini surfactants and their modified clay

RichHTML

PDF (PC)

Like

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 15

References 46

Related Articles 15

Metrics

Comments

Recommended 10

[1]	Yuting Duan, Yingmiao Zhao, Sui Shen, Zhenxi Lu, Bing Liang, Jiapeng Long. Preparation and adsorption properties of porous boron nitride materials [J]. China Surfactant Detergent & Cosmetics, 2024, 54(3): 273-281.
[2]	Shaodi Jin, Xueer Xu, Dongya Gu. Preparation and adsorption performance of tannin cured with triethylenetetramine [J]. China Surfactant Detergent & Cosmetics, 2024, 54(3): 290-297.
[3]	Keyun Hu. Preparation and paramagnetic study of Fe₃O₄-based core-shell nanostructured materials [J]. China Surfactant Detergent & Cosmetics, 2024, 54(3): 298-304.
[4]	Haokang Ai, Yajie Jiang, Yakui Wang, Lu Zhang, Tao Geng. Synthesis and properties of Gemini quaternary ammonium surfactant based on stearate [J]. China Surfactant Detergent & Cosmetics, 2024, 54(1): 16-23.
[5]	Cui Congcong,Zhang Hongli,Xuan Guangshan. Study on preparation and performance of multi-headgroup quaternary ammonium surfactant [J]. China Surfactant Detergent & Cosmetics, 2023, 53(8): 899-907.
[6]	An Rui,Zhao Qing. Progress in the adsorption of triclosan in aqueous solution [J]. China Surfactant Detergent & Cosmetics, 2023, 53(8): 945-953.
[7]	Zhou Yuan, Yang Xiuquan, Zhang Jun, Bai Liang, Wu Zhiyu. Synthesis and properties of alkyl polyglucoside sulfosuccinate salts with different degrees of esterification [J]. China Surfactant Detergent & Cosmetics, 2023, 53(7): 765-772.
[8]	Li Xiaomin. Process optimization of enzyme-catalyzed synthesis of monoglyceride and its antibacterial activity [J]. China Surfactant Detergent & Cosmetics, 2023, 53(2): 180-186.
[9]	Wang Tao, Sun Xiao, Li Zhuo, Dong Manman, Jia Hanbing, Wei Xinghua. Optimization of synthesis process of acetylvanillin and analysis of the reaction process [J]. China Surfactant Detergent & Cosmetics, 2023, 53(11): 1273-1279.
[10]	Wu Yuwen, Ma Ling, Chen Timson, Chang Kuan, Wang Jing. Scientific foundations of hair and scalp care （I） Effects of moisture on the properties of hair and the study on moisturizing efficacy [J]. China Surfactant Detergent & Cosmetics, 2023, 53(1): 8-15.
[11]	Mi Haoyu,Liu Wanyi,Duan Hongyu,Zhang Tianchun,Han Luping. Study on the synthesis and antioxidant activities of a sulfated cornstalk xylan [J]. China Surfactant Detergent & Cosmetics, 2022, 52(9): 975-980.
[12]	Wang Haobo,Yi Yun,Fu Chengbing,Liu Fei,Cao Jianxin,Pan Hongyan. Adsorption removal of Cu²⁺ and Pb²⁺ from industrial calcium chloride by modified kaolin [J]. China Surfactant Detergent & Cosmetics, 2022, 52(8): 819-826.
[13]	Zhao Fengtao,Li Xuanjing,Li Enze,Du Zhiping,Li Jianfeng,Shen Jing. Preparation of magnetic nano-Fe₃O₄and its application in wastewater treatment [J]. China Surfactant Detergent & Cosmetics, 2022, 52(8): 882-891.
[14]	Zhao Shufen,Zheng Danmiao,Liu Huaxi,Song Songlin,Chen Zhan,Yang Ningyuan,Wei Xingchuan. Progress in synthesis and application of rosin based gemini surfactants [J]. China Surfactant Detergent & Cosmetics, 2022, 52(8): 892-903.
[15]	Xuan Chao,Hu Changrong,Yi Yun,Liu Fei,Cao Jianxin,Pan Hongyan. Analysis of phosphorus adsorption performance and adsorption kinetics of phosphogypsum in loess soil [J]. China Surfactant Detergent & Cosmetics, 2022, 52(6): 606-612.