Synthesis and Application of Rosin-Based Polyoxyethylene Ether Non-Ionic Gemini Surfactant

Abstract

In this research, novel rosin-based non-ionic Gemini surfactants (RNGSs) were synthesized from rosin derivatives, dehydroabietic acid (DAA) and dehydroabietylamine (DHAA), via addition and alkylation reactions. The structures of the synthesized surfactants were characterized by Fourier transform infrared (FTIR) spectroscopy and proton nuclear magnetic resonance (¹H NMR) spectroscopy. The surface activity, aggregation property, and foaming property of RNGSs in aqueous solution were investigated by surface tension measurement and dynamic light scattering (DLS). Furthermore, the cloud point was investigated to evaluate the upper temperature limit for practical application of the surfactants. To evaluate the potential of RNGSs for enhanced oil recovery (EOR), their interfacial tension (IFT), static adsorption capacity, salt tolerance, and emulsion stability were examined. The lowest critical micelle concentration (CMC) of RNGSs was 8.51 × 10^-6 mol/L, lower than that of the commonly used non-ionic surfactant OP-10 (1.29 × 10^-4 mol/L). The cloud point of RNGSs reached 72.6 ℃. Furthermore, the tolerance to NaCl and CaCl₂ was determined to be 300 and 10 g/L, respectively. The findings indicate that the synthesized surfactants possess the potential for application in EOR.

Keywords

non-ionic Gemini surfactant / rosin derivative / enhanced oil recovery

References

[1] Zhang W J, Ye S F, Zhai Z L, et al. Preparation and application of wormlike micelles generated from a rosin—based aggregation—induced emission surfactant through coordinating aggregation[J]. Journal of Molecular Liquids, 2024, 410: 125623.

[2] Mantzaridis C, Brocas A L, Llevot A, et al. Rosin acid oligomers as precursors of DGEBA—free epoxy resins[J]. Green Chemistry, 2013, 15(11): 3091-3098.

[3] Liang T B, Zhao X R, Yuan S, et al. Surfactant—EOR in tight oil reservoirs: current status and a systematic surfactant screening method with field experiments[J]. Journal of Petroleum Science and Engineering, 2021, 196: 108097.

[4] Yu J, Xu C Q, Song X L, et al. Synthesis and properties of rosin grafted polymers via “grafting from” ATRP: the role of rosin—based initiator[J]. Industrial Crops and Products, 2021, 168: 113610.

[5] Zhai Z L, Yan X Y, Song Z Q, et al. Annular and threadlike wormlike micelles formed by a bio—based surfactant containing an extremely large hydrophobic group[J]. Soft Matter, 2018, 14(4): 499-507.

[6] Zhao Y Z, Zhou J Y, Lei F H, et al. Temperature induced multiple structure transformation and aggregation behaviors of amphiphilic acrylicpimaric acid polyglycol ester in water[J]. Polymer, 2017, 118: 49-57.

[7] Zhu X F, Zhang J, Zhou J Y, et al. Adsorption characteristics and conformational transition of polyethylene glycol—maleated rosin polyesters on the water—air surface[J]. Advanced Composites and Hybrid Materials, 2022, 5(2): 1233-1240.

[8] Pal N, Saxena N, Mandal A. Studies on the physicochemical properties of synthesized tailor—made gemini surfactants for application in enhanced oil recovery[J]. Journal of Molecular Liquids, 2018, 258: 211-224.

[9] Lei L, Xie D H, Song B L, et al. Photoresponsive foams generated by a rigid surfactant derived from dehydroabietic acid[J]. Langmuir, 2017, 33(32): 7908-7916.

[10] Liu D T, Yang X, Liu P, et al. Synthesis and characterization of gemini ester surfactant and its application in efficient fabric softening[J]. Journal of Molecular Liquids, 2020, 299: 112236.

[11] Zhao W W, Wang Y L. Coacervation with surfactants: from single—chain surfactants to gemini surfactants[J]. Advances in Colloid and Interface Science, 2017, 239: 199-212.

[12] Al—Azani K, Abu—Khamsin S, Kamal M S, et al. Role of injection rate on chemically enhanced oil recovery using a gemini surfactant under harsh conditions[J]. Energy & Fuels, 2024, 38(5): 3682-3692.

[13] Deng X, Kamal M S, Patil S, et al. Wettability alteration on carbonate rock by the mixture of the gemini surfactant and chelating agent[J]. Energy & Fuels, 2022, 36(22): 13652-13664.

[14] Yao Y, Fu Y F, Zhang L, et al. Synthesis, properties, and applications of an anionic—nonionic Gemini surfactant for highly efficient remediation of perchloroethylene—contaminated aquifers[J]. Journal of Cleaner Production, 2022, 333: 130143.

[15] Tan W X, Lin Z T, Bu H T, et al. Nano—micelles based on a rosin derivative as potent sorbents and sinking agents with high absorption capabilities for the removal of metal ions[J]. RSC Advances, 2012, 2(18): 7279-7289.

[16] Pan Y Q, Ge B Q, Zhang Y L, et al. Surface activity and cleaning performance of Gemini surfactants with rosin groups[J]. Journal of Molecular Liquids, 2021, 336: 116222.

[17] Xu Y R, Niu Y F, Wu C H, et al. Synthesis, characterization, antifungal properties of quaternary ammonium salts derived from natural rosin[J]. Biomass Conversion and Biorefinery, 2024, 14(16): 18803-18811.

[18] Yan X Y, Zhai Z L, Song Z Q, et al. Synthesis and properties of polyester—based polymeric surfactants from diterpenic rosin[J]. Industrial Crops and Products, 2017, 108: 371-378.

[19] Wang M G, Yang X F, Han B, et al. Design and properties of natural rosin—based phosphoester functional surfactants[J]. Molecules, 2023, 28(7): 3091.

[20] Deng W X, Zhang Y C, Zhong Y W, et al. Synthesis and thermodynamic properties of rosin—based cationic gemini surfactants[J]. Journal of Surfactants and Detergents, 2014, 17(3): 453-458.

[21] Feng L, Xie D H, Song B L, et al. Aggregate evolution in aqueous solutions of a Gemini surfactant derived from dehydroabietic acid[J]. Soft Matter, 2018, 14(7): 1210-1218.

[22] Feng H Y, Pan Y Q, Zhang Y J, et al. Surface activity and cleaning performance of rosin—based quaternary ammonium salt type asymmetric Gemini surfactants[J]. Chinese Journal of Chemical Engineering, 2024, 73: 70-80.

[23] Liu J H, Liu Z, Yuan T J, et al. Synthesis and properties of zwitterionic gemini surfactants for enhancing oil recovery[J]. Journal of Molecular Liquids, 2020, 311: 113179.

[24] Bao X N, Li Y C, Zhang W D, et al. A new thermal stable and salt tolerant alkyl polyether benzyl sulfonate surfactant with ultralow interfacial tensions for enhanced oil recovery[J]. Energy & Fuels, 2023, 37(3): 1828-1835.

[25] Cheng Y Q, Xue L N, Niu C R, et al. Synthesis and properties of a novel asymmetric gemini surfactant based on siloxane skeleton[J]. Journal of Molecular Liquids, 2019, 296: 112073.

[26] Kumar S, Saxena N, Mandal A. Synthesis and evaluation of physicochemical properties of anionic polymeric surfactant derived from Jatropha oil for application in enhanced oil recovery[J]. Journal of Industrial and Engineering Chemistry, 2016, 43: 106-116.

[27] Zhao W H, Cheng Y Q, Lu S, et al. Synthesis and surface activity of two novel phosphate silicone surfactants[J]. Journal of Molecular Liquids, 2023, 390: 123154.

[28] Li P, Guo Y X, Lu Z, et al. Syntheses, surface activities and aggregation morphologies of a series of novel itaconic acid based asymmetrical gemini surfactants[J]. Journal of Molecular Liquids, 2019, 290: 111218.

[29] Su S K, Lin L H, Lai Y C. Surface activity and cleavability of gemini surfactants featuring hydrophilic spacer groups[J]. Journal of Surfactants and Detergents, 2012, 15(6): 745-750.

[30] Dong Q W, Li X, Dong J X. Synthesis and properties of ethoxylated vicinal diol nonionic surfactants with double hydrophilic head groups[J]. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2022, 634: 127971.

[31] Chen S Y, Liu H J, Sun H, et al. Synthesis and physiochemical performance evaluation of novel sulphobetaine zwitterionic surfactants from lignin for enhanced oil recovery[J]. Journal of Molecular Liquids, 2018, 249: 73-82.

[32] Man Z Q, Wu W X. Study on the synthesis, surface activity, and self—assembly behavior of anionic non—ionic gemini surfactants[J]. Molecules, 2024, 29(8): 1725.

[33] Yang C P, Song Z Z, Zhao J J, et al. Self—assembly properties of ultra—long—chain gemini surfactants bearing multiple amide groups with high performance in fracturing fluid application[J]. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2017, 523: 62-70.

[34] Cai B, Li X F, Yang Y, et al. Surface properties of Gemini surfactants with pyrrolidinium head groups[J]. Journal of Colloid and Interface Science, 2012, 370(1): 111-116.

[35] Cheng Y M, Liu X, Lei Q F, et al. Development of novel anionic Gemini surfactants and application in fabricating hierarchical silver microparticles for surface—enhanced Raman spectroscopy[J]. Journal of Colloid and Interface Science, 2017, 505: 1074-1081.

[36] Xie Y C, Li J, Zhu R H, et al. Synthesis, surface activity, thermodynamic parameters, and performance evaluation of branched carboxylate gemini surfactants[J]. Journal of Surfactants and Detergents, 2019, 22(3): 421-430.

[37] Tan J L, Xiao M H, Hu Q H. Aggregation behavior of “linear” trisiloxane surfactant with different terminal groups (CH₃—, ClCH₂—, and CF₃—) in aqueous solution [J]. The Journal of Physical Chemistry B, 2019, 123(16): 3543-3549.

[38] Ma B D, Gao B Y, Zhang L, et al. Influence of polymer on dynamic interfacial tensions of EOR surfactant solutions[J]. Journal of Applied Polymer Science, 2014, 131(15): 40562.

[39] Liu Z L, Zhao G, Brewer M, et al. Comprehensive review on surfactant adsorption on mineral surfaces in chemical enhanced oil recovery[J]. Advances in Colloid and Interface Science, 2021, 294: 102467.

[40] Atta D Y, Negash B M, Yekeen N, et al. A state—of—the—art review on the application of natural surfactants in enhanced oil recovery[J]. Journal of Molecular Liquids, 2021, 321: 114888.

[41] Lashkarbolooki M, Ayatollahi S, Riazi M. The impacts of aqueous ions on interfacial tension and wettability of an asphaltenic—acidic crude oil reservoir during smart water injection[J]. Journal of Chemical & Engineering Data, 2014, 59(11): 3624-3634.

[42] Sakthivel S, Gardas R L, Sangwai J S. Effect of alkyl ammonium ionic liquids on the interfacial tension of the crude oil—water system and their use for the enhanced oil recovery using ionic liquid—polymer flooding[J]. Energy & Fuels, 2016, 30(3): 2514-2523.

[43] Rostami A, Hashemi A, Ali Takassi M, et al. Experimental assessment of a lysine derivative surfactant for enhanced oil recovery in carbonate rocks: mechanistic and core displacement analysis[J]. Journal of Molecular Liquids, 2017, 232: 310-318.

[44] Guo J X, Shi X, Yang Z G, et al. Synthesis of temperature—resistant and salt—tolerant surfactant SDB—7 and its performance evaluation for Tahe Oilfield flooding (China)[J]. Petroleum Science, 2014, 11(4): 584-589.

[45] Sharifi A, Miri R, Riazi M. A holistic review of harsh conditions resistant surfactants for enhanced oil recovery in dense carbonate reservoir[J]. Fuel, 2023, 353: 129109.

[46] Afolabi F, Mahmood S M, Yekeen N, et al. Polymeric surfactants for enhanced oil recovery: a review of recent progress[J]. Journal of Petroleum Science and Engineering, 2022, 208: 109358.

[47] Kalam S, Abu—Khamsin S A, Patil S, et al. Adsorption reduction of a gemini surfactant on carbonate rocks using formic acid: static and dynamic conditions[J]. Fuel, 2023, 345: 128166.

[48] Jian G Q, Puerto M, Wehowsky A, et al. Characterizing adsorption of associating surfactants on carbonates surfaces[J]. Journal of Colloid and Interface Science, 2018, 513: 684-692.