Progress in synthesis and application of zwitterionic Gemini surfactants

Yuqiao CHENG, Yang YANG, Chunrong NIU, Zhe FENG, Wenhui ZHAO, Shuang LU

PDF(829 KB)
PDF(829 KB)
Front. Mater. Sci. ›› 2019, Vol. 13 ›› Issue (3) : 242-257. DOI: 10.1007/s11706-019-0473-0
REVIEW ARTICLE

Progress in synthesis and application of zwitterionic Gemini surfactants

Author information +
History +

Abstract

Zwitterionic Gemini surfactants have the Gemini molecular structure in which there are both multiple lipophilic groups and multiple hydrophilic groups. However, their hydrophilic groups have different charges. Due to the special molecular structure, this kind of surfactants possesses excellent properties, including high surface activities, isoelectric point (IP), low critical micelle concentration (CMC), less toxicity, low irritating, biodegradability, bioactive, interface modification, and so on. In this review, synthetic strategies of three kinds of zwitterionic Gemini surfactants, i.e., anionic– cationic, cationic–nonionic and anionic–nonionic Gemini surfactants, are discussed, and their potential applications in life sciences, chemical industry and enhanced oil recovery (EOR) are illustrated. Their future development is also prospected.

Keywords

zwitterionic Gemini surfactant / high performance / synthesis; application / chemical industry

Cite this article

Download citation ▾
Yuqiao CHENG, Yang YANG, Chunrong NIU, Zhe FENG, Wenhui ZHAO, Shuang LU. Progress in synthesis and application of zwitterionic Gemini surfactants. Front. Mater. Sci., 2019, 13(3): 242‒257 https://doi.org/10.1007/s11706-019-0473-0

References

[1]
Bunton C A, Robinson L, Schaak J, . Catalysis of nucleophilic substitutions by micelles of dicationic detergents. Journal of Organic Chemistry, 1971, 36(16): 2346–2350
CrossRef Google scholar
[2]
Menger F M, Littau C A. Gemini surfactants: Synthesis and properties. Journal of the American Chemical Society, 1991, 113(4): 1451–1452
CrossRef Google scholar
[3]
Kumar N, Tyagi R. Industrial applications of dimeric surfactants: A review. Journal of Dispersion Science and Technology, 2014, 35(2): 205–214
CrossRef Google scholar
[4]
Ao M, Xu G, Pang J, . Comparison of aggregation behaviors between ionic liquid-type imidazolium Gemini surfactant [C12-4-C12im]Br2 and its monomer [C12mim]Br on silicon wafer. Langmuir, 2009, 25(17): 9721–9727
CrossRef Pubmed Google scholar
[5]
Huang Z, Cheng C, Liu Z, . Gemini surfactant: A novel flotation collector for harvesting of microalgae by froth flotation. Bioresource Technology, 2019, 275: 421–424
CrossRef Pubmed Google scholar
[6]
Liu J M, Ma X Y, Zhang S J, . Cationic gemini surfactant templated magnetic cubic mesoporous silica and its application in the magnetic dispersive solid phase extraction of endocrine-disrupting compounds from the migrants of food contact materials. Microchemical Journal, 2019, 145: 606–613
CrossRef Google scholar
[7]
Zhang S, Xu T, Liu Q, . Cationic gemini surfactant-resorcinol-aldehyde resin and its application in the extraction of endocrine disrupting compounds from food contacting materials. Food Chemistry, 2019, 277: 407–413
CrossRef Pubmed Google scholar
[8]
Sharma R, Kamal A, Abdinejad M, . Advances in the synthesis, molecular architectures and potential applications of Gemini surfactants. Advances in Colloid and Interface Science, 2017, 248: 35–68
CrossRef Pubmed Google scholar
[9]
Hussain S M S, Fogang L T, Kamal M S. Synthesis and performance evaluation of betaine type zwitterionic surfactants containing different degrees of ethoxylation. Journal of Molecular Structure, 2018, 1173: 983–989
CrossRef Google scholar
[10]
Xue C L, Zhu H L, Zhang T T, . Synthesis and properties of novel alkylbetaine zwitterionic gemini surfactants derived from cyanuric chloride. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2011, 375(1–3): 141–146
CrossRef Google scholar
[11]
Li P, Yang C, Cui Z, . A new type of sulfobetaine surfactant with double alkyl polyoxyethylene ether chains for enhanced oil recovery. Journal of Surfactants and Detergents, 2016, 19(5): 967–977
CrossRef Google scholar
[12]
Muggeridge A, Cockin A, Webb K, . Recovery rates, enhanced oil recovery and technological limits. Philosophical Transactions of the Royal Society A: Mathematical Physical and Engineering Sciences, 2014, 372(2006): 20120320
CrossRef Google scholar
[13]
Olajire A A. Review of ASP EOR (alkaline surfactant polymer enhanced oil recovery) technology in the petroleum industry: Prospects and challenges. Energy, 2014, 77(SI): 963–982
CrossRef Google scholar
[14]
Ren Z H, Chen D J, Luo Y. Adsorption of amino sulfonate amphoteric surfactants on quartz sand. China Surfactant Detergent & Cosmetics, 2010, 40(6): 410–413 (in Chinese)
[15]
Guttmann A T. Sulfoalkylated imidazolines. US Patent, 3244724, 1966-04-05
[16]
Yoshimura T, Ichinokawa T, Kaji M, . Synthesis and surface-active properties of sulfobetaine-type zwitterionic gemini surfactants. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2006, 273(1–3): 208–212
CrossRef Google scholar
[17]
Hirao M, Ito-Akita K, Ohno H. Polymerization of molten salt monomers having a phenylimidazolium group. Polymers for Advanced Technologies, 2000, 11(8–12): 534–538
CrossRef Google scholar
[18]
Hirao M, Sugimoto H, Ohno H. Preparation of novel room-temperature molten salts by neutralization of amines. Journal of the Electrochemical Society, 2000, 147(11): 4168–4172
CrossRef Google scholar
[19]
Hirao M, Ito K, Ohno H. Preparation and polymerization of new organic molten salts; N-alkylimidazolium salt derivatives. Electrochimica Acta, 2000, 45(8–9): 1291–1294
CrossRef Google scholar
[20]
Zheng Y C, Ren Z H, Mei P, . Interactions between a sulfobetaine-type zwitterionic Gemini surfactant and fatty acid alkanolamide in aqueous micellar solution. Journal of Surfactants and Detergents, 2016, 19(2): 283–288
CrossRef Google scholar
[21]
Nyuta K, Yoshimura T, Esumi K. Surface tension and micellization properties of heterogemini surfactants containing quaternary ammonium salt and sulfobetaine moiety. Journal of Colloid and Interface Science, 2006, 301(1): 267–273
CrossRef Pubmed Google scholar
[22]
Perroni D V, Mahanthappa M K. Inverse Pm3 ¯n cubic micellar lyotropic phases from zwitterionic triazolium Gemini surfactants. Soft Matter, 2013, 9(33): 7919–7922
CrossRef Google scholar
[23]
Yoshizawa M, Hirao M, Ito-Akita K, . Ion conduction in zwitterionic-type molten salts and their polymers. Journal of Materials Chemistry, 2001, 11(4): 1057–1062
CrossRef Google scholar
[24]
Feng J, Liu X P, Zhang L, . Dilational viscoelasticity of the zwitterionic Gemini surfactants with polyoxyethylene spacers at the interfaces. Journal of Dispersion Science and Technology, 2011, 32(11): 1537–1546
CrossRef Google scholar
[25]
Geng X F, Hu X Q, Xia J J, . Synthesis and surface activities of a novel di-hydroxyl-sulfate-betaine-type zwitterionic Gemini surfactants. Applied Surface Science, 2013, 271: 284–290
CrossRef Google scholar
[26]
Qu G M, Hu X Q, Xia J J. Study on synthesis and properties of sulfonate zwitterionic Gemini surfactants. In: Chinese Chemical Society. The 30th Annual Meeting of the Chinese Chemical Society - 31st Chapter: Colloids and Interface Chemistry, 2016, 1
[27]
Bordes R, Holmberg K. Amino acid-based surfactants — do they deserve more attention? Advances in Colloid and Interface Science, 2015, 222: 79–91
CrossRef Pubmed Google scholar
[28]
Xie Z F, Feng Y J. Synthesis and properties of alkylbetaine zwitterionic Gemini surfactants. Journal of Surfactants and Detergents, 2010, 13(1): 51–57
CrossRef Google scholar
[29]
Lu H, Xue M, Wang B, . pH-Regulated surface property and pH-reversible micelle transition of a tertiary amine-based Gemini surfactant in aqueous solution. Soft Matter, 2015, 11(47): 9135–9143
CrossRef Pubmed Google scholar
[30]
Lu H, Zheng C, Xue M, . pH-Regulated surface properties and pH-reversible micelle transition of a zwitterionic Gemini surfactant in aqueous solution. Physical Chemistry Chemical Physics, 2016, 18(47): 32192–32197
CrossRef Pubmed Google scholar
[31]
Zhou M, Luo G, Wang X W, . Synthesis and surface active properties of tri[(N-alkyl-N-ethyl-N-sodium carboxymethyl)-2-ammonium bromide ethylene] amines. Journal of Surfactants and Detergents, 2015, 18(5): 837–844
CrossRef Google scholar
[32]
Zhou M, Huang Z, Yu S, . Synthesis and surface active properties of novel oligomer betaine surfactants. Tenside, Surfactants, Detergents, 2016, 53(2): 134–139
CrossRef Google scholar
[33]
Jaeger D A, Li B, Clark T. Cleavable double-chain surfactants with one cationic and one anionic head group that form vesicles. Langmuir, 1996, 12(18): 4314–4316
CrossRef Google scholar
[34]
Nyuta K, Yoshimura T, Tsuchiya K, . Zwitterionic heterogemini surfactants containing ammonium and carboxylate headgroups 2: aggregation behavior studied by SANS, DLS, and cryo-TEM. Journal of Colloid and Interface Science, 2012, 370(1): 80–85
CrossRef Pubmed Google scholar
[35]
Yoshimura T, Nyuta K, Esumi K. Zwitterionic heterogemini surfactants containing ammonium and carboxylate headgroups. 1. Adsorption and micellization. Langmuir, 2005, 21(7): 2682–2688
CrossRef Pubmed Google scholar
[36]
Nayak B B, Patel S, Behera P K, . A novel class of zwitterionic Gemini surfactants. ARKIVOC, 2006, 14: 22–27
[37]
Zhou T, Zhao J. Synthesis and thermotropic liquid crystalline properties of heterogemini surfactants containing a quaternary ammonium and a hydroxyl group. Journal of Colloid and Interface Science, 2009, 331(2): 476–483
CrossRef Pubmed Google scholar
[38]
Zhou T, Zhao J. Synthesis and thermotropic liquid crystalline properties of zwitterionic gemini surfactants containing a quaternary ammonium and a sulfate group. Journal of Colloid and Interface Science, 2009, 338(1): 156–162
CrossRef Pubmed Google scholar
[39]
Peresypkin A V, Menger F M. Zwitterionic geminis. Coacervate formation from a single organic compound. Organic Letters, 1999, 1(9): 1347–1350
CrossRef Google scholar
[40]
Kumar A, Alami E, Holmberg K, . Branched zwitterionic gernini surfactants micellization and interaction with ionic surfactants. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2003, 228(1–3): 197–207
CrossRef Google scholar
[41]
Ansari W H, Noori S, Naqvi A Z, . Interaction between zwitterionic surfactants and amphiphilic drug: A tensiometric study. Zeitschrift für Physikalische Chemie - International Journal of Research in Physical Chemistry & Chemical Physics, 2013, 227(4): 441–458
CrossRef Google scholar
[42]
Mobin M, Noori S. Adsorption and corrosion inhibition behaviour of zwitterionic Gemini surfactant for mild steel in 0.5 M HCl. Tenside, Surfactants, Detergents, 2016, 53(4): 357–367
CrossRef Google scholar
[43]
Sun Y, Feng Y, Dong H, . Synthesis and aqueous solution properties of homologous Gemini surfactants with different head groups. Central European Journal of Chemistry, 2007, 5(2): 620–634
CrossRef Google scholar
[44]
Dong Z, Zheng Y, Zhao J. Synthesis, physico-chemical properties and enhanced oil recovery flooding evaluation of novel zwitterionic Gemini surfactants. Journal of Surfactants and Detergents, 2014, 17(6): 1213–1222
CrossRef Google scholar
[45]
Li Y R, Cao B, Ye W. Study on the synthetic process of new type of hydroxyl-containing phosphonate quaternary ammonium salt amphoteric surfactant. Speciality Petrochemicals, 1991, (6): 14–17 (in Chinese)
[46]
Feng D Q, Liu G, Ma G, . Phosphodiesters quaternary ammonium nanoparticles as label-free light scattering probe for turn-off detection of tyrosine. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2019, 208: 1–6
CrossRef Pubmed Google scholar
[47]
Chen X, Liang S, Zhu L, . High-sensitivity determination of curcumin in human urine using gemini zwitterionic surfactant as a probe by resonance light scattering technique. Phytochemical Analysis, 2012, 23(5): 456–461
CrossRef Pubmed Google scholar
[48]
Cherkasov R A, Galkin V I. The Kabachnik–Fields reaction: synthetic potential and the problem of the mechanism. Russian Chemical Reviews, 1998, 67(10): 857–882
CrossRef Google scholar
[49]
Yoshimura T, Nyuta K. Dynamic surface tension of heterogemini surfactants with quaternary ammonium salt and gluconamide or sulfobetaine headgroups. Journal of Oleo Science, 2017, 66(10): 1139–1147
CrossRef Pubmed Google scholar
[50]
Rist O, Rike A, Ljones L, . Synthesis of novel diammonium gemini surfactants. Molecules, 2001, 6(12): 979–987
CrossRef Google scholar
[51]
Nyuta K, Yoshimura T, Tsuchiya K, . Adsorption and aggregation properties of heterogemini surfactants containing a quaternary ammonium salt and a sugar moiety. Langmuir, 2006, 22(22): 9187–9191
CrossRef Pubmed Google scholar
[52]
Zhang J X, Zheng Y P, Yu P Y, . Synthesis, characterization and surface-activity of a polyoxyethylene ether trimeric quater-nary ammonium surfactant. Journal of Surfactants and Detergents, 2010, 13(2): 155–158
CrossRef Google scholar
[53]
Renouf P, Mioskowski C, Lebeau L, . Dimeric surfactants: First synthesis of an asymmetrical gemini compound. Tetrahedron Letters, 1998, 39(11): 1357–1360
CrossRef Google scholar
[54]
Alami E, Holmberg K, Eastoe J. Adsorption properties of novel gemini surfactants with nonidentical head groups. Journal of Colloid and Interface Science, 2002, 247(2): 447–455
CrossRef Pubmed Google scholar
[55]
Lai C C, Chen K M. Preparation and surface activity of polyoxyethylene-carboxylated modified Gemini surfactants. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2008, 320(1–3): 6–10
CrossRef Google scholar
[56]
Shen Z, Li Y, Sha O, . Synthesis and properties of nonionic–anionic gemini surfactants with high activity. Advances in Fine Petrochemicals, 2011, 12(09): 25–29
[57]
Egan E A, Notter R H, Kwong M S, . Natural and artificial lung surfactant replacement therapy in premature lambs. Journal of Applied Physiology: Respiratory, Environmental and Exercise Physiology, 1983, 55(3): 875–883
CrossRef Pubmed Google scholar
[58]
Naqvi A Z, Noori S, Kabir-ud-Din. Effect of surfactant structure on the mixed micelle formation of cationic gemini-zwitterionic phospholipid systems. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2015, 477: 9–18
CrossRef Google scholar
[59]
Noori S, Naqvi A Z, Ansari W H, . Effect of asymmetric dimeric zwitterionic surfactants on micellization behavior of amphiphilic drugs. Journal of Solution Chemistry, 2015, 44(6): 1292–1309
CrossRef Google scholar
[60]
Qu Z. Applications of H-phosphonates in synthesis of phosphorus-containing functional compounds. Dissertation for the Doctoral Degree. Zhengzhou, China: Zhengzhou University, 2012 (in Chinese)
[61]
Lukác M, Mojzis J, Mojzisová G, . Dialkylamino and nitrogen heterocyclic analogues of hexadecylphosphocholine and cetyltrimetylammonium bromide: effect of phosphate group and environment of the ammonium cation on their biological activity. European Journal of Medicinal Chemistry, 2009, 44(12): 4970–4977
CrossRef Pubmed Google scholar
[62]
Strickley R G. Solubilizing excipients in oral and injectable formulations. Pharmaceutical Research, 2004, 21(2): 201–230
CrossRef Pubmed Google scholar
[63]
Blanzat M, Perez E, Rico-Lattes I, . New catanionic glycolipids. 1. Synthesis, characterization, and biological activity of double-chain and Gemini catanionic analogues of galactosylceramide (galβ1cer). Langmuir, 1999, 15(19): 6163–6169
[64]
Wang F, Hu S. Direct electron-transfer of myoglobin within a new zwitterionic gemini surfactant film and its analytical application for H2O2 detection. Colloids and Surfaces B: Biointerfaces, 2008, 63(2): 262–268
CrossRef Pubmed Google scholar
[65]
Tiecco M, Cardinali G, Roscini L, . Biocidal and inhibitory activity screening of de novo synthesized surfactants against two eukaryotic and two prokaryotic microbial species. Colloids and Surfaces B: Biointerfaces, 2013, 111: 407–417
CrossRef Pubmed Google scholar
[66]
Choi H, Liu T, Qiao H, . Biomimetic nano-surfactant stabilizes sub-50 nanometer phospholipid particles enabling high paclitaxel payload and deep tumor penetration. Biomaterials, 2018, 181: 240–251
CrossRef Pubmed Google scholar
[67]
Kaur R, Kumar S, Aswal V K, . Influence of headgroup on the aggregation and interactional behavior of twin-tailed cationic surfactants with pluronics. Langmuir, 2013, 29(38): 11821–11833
CrossRef Pubmed Google scholar
[68]
Wang X C, Wang X Q, Qing T T. The application of Gemini surfactant in leather industry. Leather Science and Engineering, 2015, 25(3): 32–37 (in Chinese)
[69]
Cai M, Zhang M, Ma P. Synthesis and applications of alkylbenzene sulfonate gemini surfactants. Journal of Dispersion Science and Technology, 2010, 31(12): 1633–1637
CrossRef Google scholar
[70]
Fischer P, Wu H. Morphological transitions in dilute solutions of sugar-based zwitterionic dimer betaine surfactants. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2008, 326(1–2): 103–108
CrossRef Google scholar
[71]
Chen K, Locke D C, Maldacker T, . Separation of ergot alkaloids by micellar electrokinetic capillary chromatography using cationic Gemini surfactants. Journal of Chromatography A, 1998, 822(2): 281–290
CrossRef Pubmed Google scholar
[72]
Van der Voort P, Vansant E F. The synthesis of stable, hydrophobic MCM-48/VOx catalysts, using alkylchlorosilanes as coupling agents for the molecular designed dispersion of VO(acac)2. Microporous and Mesoporous Materials, 2000, 38(2–3): 385–390
CrossRef Google scholar
[73]
Chen S, Liu H, Sun H, . Synthesis and physiochemical performance evaluation of novel sulphobetaine zwitterionic surfactants from lignin for enhanced oil recovery. Journal of Molecular Liquids, 2018, 249: 73–82
CrossRef Google scholar
[74]
Pal N, Saxena N, Mandal A. Synthesis, characterization, and physicochemical properties of a series of quaternary Gemini surfactants with different spacer lengths. Colloid & Polymer Science, 2017, 295(12): 2261–2277
CrossRef Google scholar
[75]
Shehzad F, Hussein I A, Kamal M S, . Polymeric surfactants and emerging alternatives used in the demulsification of produced water: A review. Polymer Reviews, 2018, 58(1): 63–101
CrossRef Google scholar
[76]
Lu J, Goudarzi A, Chen P, . Enhanced oil recovery from high-temperature, high-salinity naturally fractured carbonate reservoirs by surfactant flood. Journal of Petroleum Science and Engineering, 2014, 124: 122–131
CrossRef Google scholar
[77]
Hussain S M S, Kamal M S, Fogang L T. Effect of internal olefin on the properties of betaine-type zwitterionic surfactants for enhanced oil recovery. Journal of Molecular Liquids, 2018, 266: 43–50
CrossRef Google scholar
[78]
Tagavifar M, Xu K, Jang S H, . Spontaneous and flow-driven interfacial phase change: dynamics of microemulsion formation at the pore scale. Langmuir, 2017, 33(45): 13077–13086
CrossRef Pubmed Google scholar
[79]
Madani M, Zargar G, Takassi M A, . Fundamental investigation of an environmentally-friendly surfactant agent for chemical enhanced oil recovery. Fuel, 2019, 238: 186–197
CrossRef Google scholar
[80]
Takassi M A, Zargar G, Madani M, . The preparation of an amino acid-based surfactant and its potential application as an EOR agent. Petroleum Science and Technology, 2017, 35(4): 385–391
CrossRef Google scholar
[81]
Shadizadeh S S, Kharrat R. Experimental investigation of matricaria chamomilla extract effect on oil–water interfacial tension: usable for chemical enhanced oil recovery. Petroleum Science and Technology, 2015, 33(8): 901–907
CrossRef Google scholar
[82]
Al-Sabagh A M. Surface activity and thermodynamic properties of water-soluble polyester surfactants based on 1,3-dicarboxymethoxybenzene used for enhanced oil recovery. Polymers for Advanced Technologies, 2000, 11(1): 48–56
CrossRef Google scholar
[83]
Cao X C, Li Y Y, Ke K. Research progress in application of surfactants in petroleum engineering. Contemporary Chemical Industry, 2017, 46(6): 1222–1224, 1234 (in Chinese)
[84]
Kamal M S, Hussein I A, Sultan A S. Review on surfactant flooding: phase behavior, retention, IFT, and field applications. Energy & Fuels, 2017, 31(8): 7701–7720
CrossRef Google scholar
[85]
Pal S, Mushtaq M, Banat F, . Review of surfactant-assisted chemical enhanced oil recovery for carbonate reservoirs: challenges and future perspectives. Petroleum Science, 2018, 15(1): 77–102
CrossRef Google scholar
[86]
Raffa P, Broekhuis A A, Picchioni F. Polymeric surfactants for enhanced oil recovery: A review. Journal of Petroleum Science Engineering, 2016, 145: 723–733
CrossRef Google scholar
[87]
Ren H J, Chen W, Wang X H. Synthesis and application performance of amphiprotic gemini surface active agent. Applied Chemical Industry, 2019, 48(3): 613‒615 (in Chinese)
[88]
Yan L M, Ma J, Li Y L, . Surface and interfacial properties of 1,3-dialkyl glyceryl ether hydroxypropyl sulfonates as surfactants for enhanced oil recovery. Journal of Dispersion Science and Technology, 2018, 39(9): 1335–1343
CrossRef Google scholar
[89]
Almahfood M, Bai B. The synergistic effects of nanoparticle-surfactant nanofluids in EOR applications. Journal of Petroleum Science Engineering, 2018, 171: 196–210
CrossRef Google scholar
[90]
Bracic M, Fras-Zemljic L, Kogej K, . Bioactive nano-coatings from hyaluronic acid and a lysine-derived surfactant. Abstracts of Papers of the American Chemical Society, 2017, 253: 480
[91]
Chen X, Liu J B, Chen Y. Properties of nano-CaCO3 modified by a serious of phosphate surfactants and their application in PVC. Journal of Southern Yangtze University (Natural Science Edition), 2002, 1(3): 266–268 (in Chinese)
[92]
El Achouri M, Kertit S, Gouttaya H M, . Corrosion inhibition of iron in 1 M HCl by some gemini surfactants in the series of alkanediyl-α,ω-bis-(dimethyl tetradecyl ammonium bromide). Progress in Organic Coatings, 2001, 43(4): 267–273
CrossRef Google scholar

RIGHTS & PERMISSIONS

2019 Higher Education Press and Springer-Verlag GmbH Germany, part of Springer Nature
AI Summary AI Mindmap
PDF(829 KB)

Accesses

Citations

Detail

Sections
Recommended

/