Self-assembly properties of ultra-long-chain gemini surfactants bearing multiple amide groups with high performance in fracturing fluid application

Colloids and Surfaces A: Physicochemical and Engineering Aspects

Volumn 523, Issue , 2017, Pages 62-70

  Yang, Chunpeng ^a   Song, Zhaozheng ^a   Zhao, Jingjing ^b   Hu, Zhiyuan ^a   Zhang, Yuan ^a   Jiang, Qingzhe ^a  

^a CHINA UNIVERSITY OF PETROLEUM   (China)

^b BEIJING UNIVERSITY OF CHEMICAL TECHNOLOGY   (China)

Author keywords

3D network; Fracturing fluid; Gemini surfactant; Self assembly; Viscoelasticity

Indexed keywords

AMIDES; CATIONIC SURFACTANTS; CHAINS; CRITICAL MICELLE CONCENTRATION; ESTERS; HIGH RESOLUTION TRANSMISSION ELECTRON MICROSCOPY; HYDROPHOBICITY; SCANNING ELECTRON MICROSCOPY; SELF ASSEMBLY; SURFACE ACTIVE AGENTS; TRANSMISSION ELECTRON MICROSCOPY; VISCOELASTICITY;

3D NETWORKS; CATIONIC GEMINI SURFACTANT; CRITICAL MICELLE CONCENTRATION (CMC); CRYOGENIC TRANSMISSION ELECTRON MICROSCOPY (CRYO-TEM); FRACTURING OPERATIONS; GEMINI SURFACTANT; THREE-DIMENSIONAL (3D) NETWORKS; VISCOELASTIC SURFACTANTS;

FRACTURING FLUIDS;

ALKYL GROUP; AMIDE; AMMONIUM CHLORIDE; CATIONIC SURFACTANT; ESTER DERIVATIVE; VISCOELASTIC SUBSTANCE;

ARTICLE; BEHAVIORAL SCIENCE; CHEMICAL STRUCTURE; CRITICAL MICELLE CONCENTRATION; CRYOELECTRON MICROSCOPY; FLOW KINETICS; HIGH TEMPERATURE; HYDROPHOBICITY; LIQUID; MORPHOLOGY; NONHUMAN; PRIORITY JOURNAL; RAPESEED; SCANNING ELECTRON MICROSCOPE; SURFACE TENSION; SYNTHESIS; TRANSMISSION ELECTRON MICROSCOPY; VISCOELASTICITY;

EID: 85017561591     PISSN: 09277757     EISSN: 18734359     Source Type: Journal    
DOI: 10.1016/j.colsurfa.2017.03.062     Document Type: Article

References (65)

1. [1] Feng, Y., Chu, Z., pH-tunable wormlike micelles based on an ultra-long-chain pseudo gemini surfactant. Soft Matter 11 (2015), 4614–4620.
2. [2] Pei, X., Xu, Z., Song, B., Cui, Z., Zhao, J., Wormlike micelles formed in catanionic systems dominated by cationic gemini surfactant: synergistic effect with high efficiency. Colloids Surf. A 443 (2014), 508–514.
3. [3] Chu, Z., Dreiss, C.A., Feng, Y., Smart wormlike micelles. Chem. Soc. Rev. 42 (2013), 7174–7203.
4. [4] Yang, J., Cui, W., Lu, Y., Guan, B., Qiu, X., Liu, P., Instant gel formation of viscoelastic surfactant fracturing fluids by diluting through lamellar liquid crystal. J. Pet. Sci. Eng. 125 (2015), 90–94.
5. [5] Gu, M., Mohanty, K.K., Rheology of polymer-free foam fracturing fluids. J. Pet. Sci. Eng. 134 (2015), 87–96.
6. [6] Barati, R., Liang, J., A review of fracturing fluid systems used for hydraulic fracturing of oil and gas wells. J. Appl. Polym. Sci., 131, 2014 (40735-40735).
7. [7] Yan, Z., Dai, C., Zhao, M., Sun, Y., Zhao, G., Development, formation mechanism and performance evaluation of a reusable viscoelastic surfactant fracturing fluid. J. Ind. Eng. Chem. 37 (2016), 115–122.
8. [8] Dogon, D., Golombok, M., Wellbore to fracture proppant-placement-fluid rheology. J. Unconv. Gas Resour. 14 (2016), 12–21.
9. [9] Zhang, Y., An, P., Liu, X., A. worm-containing viscoelastic fluid based on single amine oxide surfactant with an unsaturated C22-tail. RSC Adv. 5 (2015), 19135–19144.
10. [10] Zhao, Z., Lü, G., Zhang, Y., Lian, S., Tian, N., Performance of EDAB-HCl acid blended system as fracturing fluids in oil fields. Chin. J. Chem. Eng. 22 (2014), 202–207.
11. [11] Al-Sadat, W., Nasser, M.S., Chang, F., Nasr-El-Din, H.A., Hussein, I.A., Laboratory evaluation of the effects of additives and pH on the thermorheological behavior of a viscoelastic zwitterionic surfactant used in acid stimulation. J. Pet. Sci. Eng. 122 (2014), 458–467.
12. [12] Chen, F., Wu, Y., Wang, M., Zha, R., Self-assembly networks of wormlike micelles and hydrophobically modified polyacrylamide with high performance in fracturing fluid application. Colloid Polym. Sci. 293 (2015), 687–697.
13. [13] Ye, Z., Zhang, X., Chen, H., Han, L., Lv, C., Su, Z., Song, J., Synthesis and characterization of an associative polymer with an octylphenyl polyoxyethylene side chain as a potential enhanced-oil-recovery chemical. J. Appl. Polym. Sci., 131, 2014 (41024-41024).
14. [14] Xu, D., Qi, B., Fang, D., Zhang, X., Zhang, T., Preparation, characterization and properties of novel cationic gemini surfactants with rigid amido spacer groups. J. Surfactants Deterg. 19 (2016), 91–99.
15. [15] Zhou, M., Xia, L., He, Y., Zhang, L., Qiao, X., Zhong, X., Synthesis of new salt-resistant sulfonate gemini surfactants with hydroxyl groups. J. Surfactants Deterg. 18 (2015), 303–308.
16. [16] Wang, Y., Han, Y., Huang, X., Cao, M., Wang, Y., Aggregation behaviors of a series of anionic sulfonate gemini surfactants and their corresponding monomeric surfactant. J. Colloid Interface Sci. 319 (2008), 534–541.
17. [17] Liu, S., Sang, R., Hong, S., Cai, Y., Wang, H., A novel type of highly effective nonionic gemini alkyl o-glucoside surfactants: a versatile strategy of design. Langmuir 29 (2013), 8511–8516.
18. [18] Han, Y., Chu, Z., Sun, H., Li, Z., Feng, Y., Green anionic wormlike micelles induced by choline. RSC Adv. 2 (2012), 3396–3402.
19. [19] Hoque, J., Gonuguntla, S., Yarlagadda, V., Aswal, V.K., Haldar, J., Effect of amide bonds on the self-assembly of gemini surfactants. Phys. Chem. Chem. Phys. 16 (2014), 11279–11288.
20. [20] Wang, Y., Tang, L., Hydrogen bonding recognition in supramolecular polymers. Prog. Chem. 19 (2007), 769–778.
21. [21] Yang, Y., Dou, D., Triply and quadruply hydrogen bonded systems: design, structure and application. Prog. Chem. 26 (2014), 706–726.
22. [22] Hoque, J., Kumar, P., Aswal, V.K., Haldar, J., Aggregation properties of amide bearing cleavable gemini surfactants by small angle neutron scattering and conductivity studies. J. Phys. Chem. B 116 (2012), 9718–9726.
23. [23] Chu, Z., Feng, Y., Empirical correlations between krafft temperature and tail length for amidosulfobetaine surfactants in the presence of inorganic salt. Langmuir 28 (2012), 1175–1181.
24. [24] Feng, D., Zhang, Y., Chen, Q., Wang, J., Li, B., Feng, Y., Synthesis and surface activities of amidobetaine surfactants with ultra-long unsaturated hydrophobic chains. J. Surfactants Deterg. 15 (2012), 657–661.
25. [25] Wu, Z., Li, H., Tu, D., Application of fourier transform infrared (FT-IR) spectroscopy combined with chemometrics for analysis of rapeseed oil adulterated with refining and purificating waste cooking oil. Food Anal. Method 8 (2015), 2581–2587.
26. [26] Chu, Z., Feng, Y., Vegetable-derived long-chain surfactants synthesized via a green route. ACS Sustain. Chem. Eng. 1 (2013), 75–79.
27. [27] Parratt, D., Smith, W.M., Thomson, G., Cameron, L.A., Butcher, R.D., Evidence that oilseed rape (brassica napus ssp. oleifera) causes respiratory illness in rural dwellers. Scott. Med. J. 40 (1995), 74–76.
28. [28] Sonnet, P.E., Foglia, T.A., Feairheller, S.H., Fatty acid selectivity of lipases: erucic acid from rapeseed oil. J. Am. Oil Chem. Soc. 70 (1993), 387–391.
29. [29] Kramer, J.K., Sauer, F.D., Pigden, W.J., High and Low Erucic Acid in Rapeseed Oils. 1983, Academic press, Toronto.
30. [30] Zamora, R., Navarro, J.L., Aguilar, I., Hidalgo, F.J., Lipid-derived aldehyde degradation under thermal conditions. Food Chem. 174 (2015), 89–96.
31. [31] Chu, Z., Feng, Y., Sun, H., Li, Z., Song, X., Han, Y., Wang, H., Aging mechanism of unsaturated long-chain amidosulfobetaine worm fluids at high temperature. Soft Matter 7 (2011), 4485–4489.
32. [32] Tehrani-Bagha, A.R., Holmberg, K., Cationic ester-containing gemini surfactants: physical-chemical properties. Langmuir 26 (2010), 9276–9282.
33. [33] A. Holland, Examination of possibly induced seismicity from hydraulic fracturing in the Eola Field, Garvin County, Oklahoma, Oklahoma Geol. Surv. Open-File Rep, OF1-2011, (2011). http://101.96.8.165/docketpublic.energy.ca.gov/PublicDocuments/12-AFC-02/TN202689_20140713T205525_Examination_of_possibly_Induced_Seismicity_for_Hydraulic_Fractu.pdf.
34. [34] Fehler, M., House, L., Phillips, W.S., Potter, R., A method to allow temporal variation of velocity in travel-time tomography using microearthquakes induced during hydraulic fracturing. Tectonophysics 289 (1998), 189–201.
35. [35] National Development and Reform Commission, Chinese Oil and Gas Industry Standards, SY/T 5107–2005 Recommended practices on measuring the properties of water-based fracturing fluid, Beijing (2005).
36. [36] Khair, E.M.M., Shicheng, Z., Shanbo, M., Mei, Z., Performance and application of new anionic D3F-AS05 viscoelastic fracturing fluid. J. Pet. Sci. Eng. 78 (2011), 131–138.
37. [37] Li, H., Yang, H., Yan, Y., Wang, Q., He, P., Synthesis and solution properties of cationic gemini surfactants with long unsaturated tails. Surf. Sci. 604 (2010), 1173–1178.
38. [38] Bhadani, A., Shrestha, R.G., Koura, S., Endo, T., Sakai, K., Abe, M., Sakai, H., Self-aggregation properties of new ester-based gemini surfactants and their rheological behavior in the presence of cosurfactant-monolaurin. Colloids Surf. A 461 (2014), 258–266.
39. [39] Akram, M., Bhat, I.A., Yaseen, Z., Kabir-ud-Din, Physicochemical investigation of novel biodegradable dicationic ester bonded m-E2-m gemini surfactants with bile salts: insights from surface tension, dynamic light scattering and fluorescence. Colloids Surf. A 444 (2014), 209–216.
40. [40] Zhang, Q., Gao, Z., Xu, F., Tai, S., Liu, X., Mo, S., Niu, F., Surface tension and aggregation properties of novel cationic gemini surfactants with diethylammonium headgroups and a diamido spacer. Langmuir 28 (2012), 11979–11987.
41. [41] Shashkina, J.A., Philippova, O.E., Zaroslov, Y.D., Khokhlov, A.R., Pryakhina, T.A., Blagodatskikh, I.V., Rheology of viscoelastic solutions of cationic surfactant. Effect of added associating polymer. Langmuir 21 (2005), 1524–1530.
42. [42] Zhou, L., Jiang, X., Li, Y., Hu, Z.C.A.X., Synthesis and properties of a novel class of gemini pyridinium surfactants. Langmuir 23 (2007), 11404–11408.
43. [43] Lu, T., Lan, Y., Liu, C., Huang, J., Wang, Y., Surface properties, aggregation behavior and micellization thermodynamics of a class of gemini surfactants with ethyl ammonium headgroups. J. Colloid Interface Sci. 377 (2012), 222–230.
44. [44] Rodrguez, A., Graciani, M.D.M., Muoz, M., Moy, I.R.A.M., Effects of ethylene glycol addition on the aggregation and micellar growth of gemini surfactants. Langmuir 22 (2006), 9519–9525.
45. [45] You, Y., Jiang, R., Ling, T., Zhao, J., Bending of the flexible spacer chain of gemini surfactant induced by hydrophobic interaction. Chin. J. Chem. 27 (2009), 469–471.
46. [46] Zhang, Z., Zheng, P., Guo, Y., Yang, Y., Chen, Z., Wang, X., An, X., Shen, W., The effect of the spacer rigidity on the aggregation behavior of two ester-containing gemini surfactants. J. Colloid Interface Sci. 379 (2012), 64–71.
47. [47] Yan, Y., Synthesis and Rheological Properties of Novel Surfactants with Long Unsaturated Tails. 2007, University of Science and Technology of China, Wuhai.
48. [48] Cao, G., Guo, X., Jia, L., Tian, X., Aggregation behaviours and bactericidal activities of novel cationic surfactants functionalized with amides and ether groups. RSC Adv. 5 (2015), 27197–27204.
49. [49] Feng, Y., Han, Y., Effect of counterion size on wormlike micelles formed by a C22-tailed anionic surfactant. J. Mol. Liq. 218 (2016), 508–514.
50. [50] Cheng, C., Oh, H., Wang, T., Raghavan, S.R., Tung, S., Mixtures of lecithin and bile salt can form highly viscous wormlike micellar solutions in water. Langmuir 30 (2014), 10221–10230.
51. [51] Lu, H., Shi, Q., Huang, Z., pH-Responsive anionic wormlike micelle based on sodium oleate induced by NaCl. J. Phys. Chem. B 118 (2014), 12511–12517.
52. [52] Loganathan, P., Vigneswaran, S., Kandasamy, J., Naidu, R., Defluoridation of drinking water using adsorption processes. J. Hazard. Mater. 248–249 (2013), 1–19.
53. [53] Raiswell, R., Tranter, M., Benning, L.G., Siegert, M., De Ath, R., Huybrechts, P., Payne, T., Contributions from glacially derived sediment to the global iron (oxyhydr)oxide cycle: implications for iron delivery to the oceans. Geochim. Cosmochim. Acta 70 (2006), 2765–2780.
54. [54] Feng, Z., Guo, X., Jia, L., Zhang, Y., Surface activity and thermodynamic data for pyridinium surfactants with an aminoacylmethyl group. Res. Chem. Intermed. 41 (2015), 3825–3835.
55. [55] Wattebled, L., Laschewsky, A., Effects of organic salt additives on the behavior of dimeric (gemini) surfactants in aqueous solution. Langmuir 23 (2007), 10044–10052.
56. [56] Kumar, R., Kalur, G.C., Ziserman, L., Danino, D., Raghavan, S.R., Wormlike micelles of a C22-tailed zwitterionic betaine surfactant: from viscoelastic solutions to elastic gels. Langmuir 23 (2007), 12849–12856.
57. [57] Yu, D., Wang, Y., Zhang, J., Tian, M., Han, Y., Wang, Y., Effects of calcium ions on solubility and aggregation behavior of an anionic sulfonate gemini surfactant in aqueous solutions. J. Colloid Interface Sci. 381 (2012), 83–88.
58. [58] Geng, X., Hu, X., Jia, X., Luo, L., Effects of sodium salicylate on the microstructure of a novel zwitterionic gemini surfactant and its rheological responses. Colloid Polym. Sci. 292 (2014), 915–921.
59. [59] Xu, X., Yang, F., Wang, N., Shen, M., Zhou, T., Wang, X., Wang, Y., Chen, X., Wang, J., Rheologic properties and molecular configuration of polymers in salt-alkali-surfactant mixed solutions. J. Dispers. Sci. Technol. 29 (2008), 101–105.
60. [60] National Development and Reform Commission, Chinese Oil and Gas Industry Standards, SY/T 6376-2008 General technical specifications of fracturing fluids, Beijing (2008).
61. [61] Xiao, B., Zhang, S., Guo, T., Zhou, T., Experimental investigation and performance evaluation of a novel high temperature tolerant seawater-based fracturing fluid. Water Resour. Manage. 28 (2014), 2767–2779.
62. [62] Zhao, G., Dai, C., Wang, S., Zhao, M., Synthesis and application of nonionic polyacrylamide with controlled molecular weight for fracturing in low permeability oil reservoirs. J. Appl. Polym. Sci., 132, 2015 (41637-41637).
63. [63] Mao, J., Yang, X., Wang, D., Li, Y., Zhao, J., A novel gemini viscoelastic surfactant (VES) for fracturing fluids with good temperature stability. RSC Adv. 6 (2016), 88426–88432.
64. [64] C. Fontana, E. Muruaga, D. Perez, G. Cavazzoli, A. Krenz, Successful application of a high temperature viscoelastic surfactant (VES) fracturing fluids under extreme conditions in Patagonian Wells, San Jorge Basin, SPE-107277, (2017).
65. [65] Elgaddafi, R., Ahmed, R., Growcock, F., Settling behavior of particles in fiber-containing Herschel Bulkley fluid. Powder Technol. 301 (2016), 782–793.