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Synthesis and characterization of a novel reticulated multi-branched fluorinated polyether demulsifier for w/o emulsion demulsification

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Abstract

In order to solve the problem of demulsification of Liaohe heavy oil W/O emulsion, phenolamine resin initiator was synthesized based on p-trifluoromethyl phenol in this paper. Polyether product was synthesized by block polymerization technology, and then toluene diisocyanate (TDI) was added for crosslinking modification, thus synthesizing a new fluorinated block polyether demulsifier called reticulated branched fluorinated (RBF). Apart from that, the structure of fluorinated polyether demulsifier was characterized by FTIR spectrum, and the surface activity of fluorinated polyether demulsifier was determined by measuring the surface tension and interfacial tension, and the thermogravimetric analysis (TGA) of RBF demulsifier was also determined. The demulsification and dehydration experiment of Liaohe crude oil emulsion was carried out. The microscopic demulsification process was analyzed and the demulsification mechanism was discussed. The experimental results showed that the synthesized RBF series fluorinated polyether demulsifier had excellent demulsification performance on Liaohe water-in-oil (W/O) emulsion. Such a result was attributed to the reticulated multi-branched structure which increased the ability of demulsifier to replace the interfacial film, so the new interfacial film was easy to break to gather with other water droplets, thus resulting in the destruction of the W/O emulsion stabilization system. When TDI dosage was 4% of polyether demulsifier mass, demulsification temperature was 60 ℃, and demulsifier dosage was 50 mg/L, the dehydration rate of RBF4 reached 95.64%, which was about 18% higher than that of demulsifier LX21. This paper provides a new type of high-efficiency demulsifier to solve the demulsification problem of heavy oil W/O emulsion in Liaohe Oilfield.

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References

  1. Kichatov B, Korshunov A, Kiverin A (2018) Combustion of the foamed emulsion containing biochar microparticles. Fuel 228(15):164–174

    Article  CAS  Google Scholar 

  2. Wang D, Yang D, Huang C, Huang Y, Zeng H (2021) Stabilization mechanism and chemical demulsification of water-in-oil and oil-in-water emulsions in petroleum industry: a review. Fuel 286(3):119390

  3. Zhou L, Zhang J, Xing L, Zhang W (2021) Applications and effects of ultrasound assisted emulsification in the production of food emulsions: a review. Trends Food Sci Technol 110:493–512

    Article  CAS  Google Scholar 

  4. Velayati A, Nouri A (2021) Role of asphaltene in stability of water-in-oil model emulsions: the effects of oil composition and size of the aggregates and droplets. Energy Fuels 35(7):5941–5954

    Article  CAS  Google Scholar 

  5. Gómora-Figueroa AP, Camacho-Velázquez RG, Guadarrama-Cetina J, Guerrero-Sarabia TI (2019) Oil emulsions in naturally fractured Porous Media. Petroleum 5(3):215–226

  6. Umar M, Su CW, Rizvi SKA, Lobonţ OR (2021) Driven by fundamentals or exploded by emotions: Detecting bubbles in oil prices. Energy 231:120873

  7. Ezzat AO, Atta AM, Al-Lohedan HA, Abdullah MM, Hashem AI (2018) Synthesis and application of poly (ionic liquid) based on cardanol as demulsifier for heavy crude oil water emulsions. Energy and Fuels 32(1):214–225

  8. Feitosa FX, Alves RS, Sant’Ana HD (2019) Synthesis and application of additives based on cardanol as demulsifier for water-in-oil emulsions. Fuel 245:21–28

  9. Ghanavati M, Shojaei MJ, Ahmad R (2013) Effects of asphaltene content and temperature on viscosity of iranian heavy crude oil: experimental and modeling study. Energy Fuels 27(12):7217–7232

    Article  CAS  Google Scholar 

  10. Ye F, Mi Y, Liu H, Zeng G, Yan X (2021) Demulsification of water-in-crude oil emulsion using natural lotus leaf treated via a simple hydrothermal process. Fuel 295(1):120596

  11. Li S, Li N, Yang S, Liu F, Zhou J (2013) The synthesis of a novel magnetic demulsifier and its application for the demulsification of oil-charged industrial wastewaters. J Mater Chem A 2(1):94–99

    Article  Google Scholar 

  12. Hjartnes TN, Srland GH, Simon SC, Sjoblom J (2019) Demulsification of crude oil emulsions tracked by pulsed field gradient nmr. part i: chemical demulsification. Ind Eng Chem Res 58(6). https://doi.org/10.1021/acs.iecr.8b05165.

  13. Akbari N, Biria D (2018) Investigation of the activity of acinetobacter calcoaceticus biodemulsifier to break stable water in oil emulsions. J Environ Chem Eng 6(4):4144–4150

    Article  CAS  Google Scholar 

  14. Abdel-Azim A, Zaki NN, Maysour ES (2015) Polyoxyalkylenated amines for breaking water-in-oil emulsions: effect of structural variations on the demulsification efficiency. Polym Adv Technol 9(2):159–166

    Article  Google Scholar 

  15. Rigoni C, Fresnais J, Talbot D, Massart R, Abou-Hassan A (2020) Magnetic field-driven deformation, attraction, and coalescence of nonmagnetic aqueous droplets in an oil-based ferrofluid. Langmuir 36(18):5048–5057

    Article  CAS  Google Scholar 

  16. Uma AA, Saaid I, Sulaimon AA, Pilus R (2018) A review of petroleum emulsions and recent progress on water-in-crude oil emulsions stabilized by natural surfactants and solids. J Pet Sci Eng 165:673–690

    Article  Google Scholar 

  17. Ma J, Yang Y, Li X, Sui H, He L (2021) Mechanisms on the stability and instability of water-in-oil emulsion stabilized by interfacially active asphaltenes: Role of hydrogen bonding reconstructing. Fuel 297:120763

  18. Cherney DP, Wu C, Thorman RM, Hegner JL, Yeganeh MS, Ferrughelli D (2015) Investigating the impact of crude oil solubility on water-in-oil emulsion stability and its relation to molecular composition of crude oil at the oil–water interface. Energy Fuels 29(6):3616–3625

    Article  CAS  Google Scholar 

  19. Sofla M, Norouzi-Apourvari S, Schaffie M (2020) The effect of magnetic field on stability of conventional and pickering water-in-crude oil emulsions stabilized with fumed silica and iron oxide nanoparticles. J Mol Liq 314:113629

  20. Shuguo A, Zhongwei L, Hao C, Zhenhu Y, Yebang T (2020) Proanthocyanidin-based polyether demulsifiers for the treatment of aging oil emulsions. Energy Fuels 34(5):5788–5797

  21. Hjartnes TN, Srland GH, Simon S (2019) Demulsification of Crude Oil Emulsions Tracked by Pulsed Field Gradient (PFG) Nuclear Magnetic Resonance (NMR). Part I: Chemical Demulsification. Ind Eng Chem Res 58(6):2310–2323

  22. Blankenburg J, Kersten E, Maciol K, Wagner M, Zarbakhsh S, Frey H (2019) The poly(propylene oxide-co-ethylene oxide) gradient is controlled by the polymerization method: determination of reactivity ratios by direct comparison of different copolymerization models. Polym Chem 10:2863–2871

    Article  CAS  Google Scholar 

  23. Fang S, Chen B, Zhang H, Zhang Y, Ming D (2016) The effects of ultrasonic time, temperature, size and polyether type on performances of magnetic flocculants for oily wastewater produced from polymer flooding treatment. Sep Sci Technol 51(18):2991–2999

    Article  CAS  Google Scholar 

  24. Kailey I, Feng X (2013) Influence of Structural Variations of Demulsifiers on their Performance. Ind Eng Chem Res 52(2):785–793

    Article  CAS  Google Scholar 

  25. Teng H, Chen C, Yan S, Ye D, Zhang L (2019) Modified hyperbranched polyethylenimine as a novel demulsifier for oil-in-water emulsions. Energy Fuels 33(10):10108–10114

    Article  CAS  Google Scholar 

  26. Alves AV, Tsianou M, Alexandridis P (2020) Fluorinated surfactant adsorption on mineral surfaces: implications for pfas fate and transport in the environment. Surfaces 3(4):516–566

    Article  CAS  Google Scholar 

  27. Hu M, Jing L, An Q, Ming W, Bian C, Chen M (2017) Tribological properties and milling performance of hss-co-e tools with fluorinated surfactants-based coatings against ti–6al–4v. Wear 376–377:134–142

    Article  Google Scholar 

  28. Bélarbi H, Bendedouch D, Bouanani F (2010) Mixed micellization properties of nonionic fluorocarbon/cationic hydrocarbon surfactants. J Surfactants Deterg 13(4):433–439

    Article  Google Scholar 

  29. Zhang J, Wang Y, Xu G, Lin M, Fan T, Yang Z (2016) Formation and rheological behavior of wormlike micelles in a catanionic system of fluoroacetic acid and tetradecyldimethylaminoxide. Soft Matter 13(3):670–676

    Article  Google Scholar 

  30. Peyre V (2009) Segregation phenomena in micelles from mixtures of fluorinated and hydrogenated surfactants. Curr Opin Colloid Interface Sci 14(5):305–314

    Article  CAS  Google Scholar 

  31. Reiner JL, Blaine AC, Higgins CP, Huset C, Keller JM (2015) Polyfluorinated substances in abiotic standard reference materials. Anal Bioanal Chem 407(11):2975

    Article  CAS  Google Scholar 

  32. Wei L, Zhang L, Chao M, Jia X, Shi L (2021) Synthesis and study of a new type of nonanionic demulsifier for chemical flooding emulsion demulsification. ACS Omega 6:17709–17719

    Article  CAS  Google Scholar 

  33. Kailey I (2017) Key performance indicators reveal the impact of demulsifier characteristics on oil sands froth treatment. Energy Fuels 31(3):2636–2642

    Article  CAS  Google Scholar 

  34. Zaltariov MF, Filip D, Macocinschi D, Ibanescu C, Sacarescu L (2021) Self-assembly and rheological behavior of chloramphenicol-based poly(ester ether)urethanes. J Polym Res 28(5):190

    Article  CAS  Google Scholar 

  35. Yan S, Hong QL, Li NB (2011) Determination of the critical premicelle concentration, first critical micelle concentration and second critical micelle concentration of surfactants by resonance rayleigh scattering method without any probe. Spectrochim Acta Part A 78(5):1403–1407

    Article  Google Scholar 

  36. Lu G, Duan YY, Wang XD (2015) Effects of free surface evaporation on water nanodroplet wetting kinetics: a molecular dynamics study. J Heat Transfer 137(9):091001

  37. Alvarado JG, Delgado-Linares JG, Forgiarini AM, Salager JL (2019) Breaking of water-in-crude oil emulsions. 8. demulsifier performance at optimum formulation is significantly improved by a small aromatic content of the oil. Energy Fuels 33(3):1928–1936

  38. Ma J, Li X, Zhang X, Sui H, Wang S (2019) A novel oxygen-containing demulsifier for efficient breaking of water-in-oil emulsions. Chem Eng J 385:123826

  39. Zhang L, He G, Ye D, Zhan N, Guo Y, Fang W (2016) Methacrylated hyperbranched polyglycerol as a high-efficiency demulsifier for oil-in-water emulsions. Energy Fuels 30(11):9939–9946

    Article  CAS  Google Scholar 

  40. Zhang L, Ying H, Yan S, Zhan N, Guo Y, Fang W (2018) Hyperbranched poly(amido amine) as an effective demulsifier for oil-in-water emulsions of microdroplets. Fuel 211:197–205

    Article  CAS  Google Scholar 

  41. Liu J, Zhong L, Yuan X, Liu Y, Zhang H (2019) Study on the re-emulsification process of water in heavy oil emulsion with addition of water-soluble viscosity reducer solution. Energy Fuels 33(11):10852–10860

    Article  CAS  Google Scholar 

  42. Peng K, Liu W, Xiong Y, Lu L, Liu J, Huang X (2018) Emulsion microstructural evolution with the action of environmentally friendly demulsifying bacteria-sciencedirect. Colloids Surf A 553:528–538

  43. Ramalho J, Lechuga FC, Lucas EF (2010) Effect of the structures of commercial poly(ethylene oxide-B-propylene oxide) demulsifier bases on the demulsificaion of water in crude oil emulsions. Quim Nova 33(8):1664–1670

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors are grateful for the reviewers’ instructive suggestions and careful proofreading.

Funding

This work was supported by the Natural Science Foundation of Shandong Province for Youth (grant nos. ZR2020QE111) and Postdoctoral Science Foundation of China (grant nos. 2020M681073).

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Authors and Affiliations

  1. Key Laboratory of Enhanced Oil Recovery, Ministry of Education, Northeast Petroleum University, Daqing, 163318, China

    Lin Zhang, Lixin Wei, Lijun Shi, Xuanrui Dai, Shijun Guo, Xinlei Jia & Chao Liu

  2. College of Chemical Engineering, Daqing Normal University, Daqing, 163712, China

    Shijun Guo & Chao Liu

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  1. Lin Zhang
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  2. Lixin Wei
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  3. Lijun Shi
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Correspondence to Lixin Wei.

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Zhang, L., Wei, L., Shi, L. et al. Synthesis and characterization of a novel reticulated multi-branched fluorinated polyether demulsifier for w/o emulsion demulsification. J Polym Res 29, 164 (2022). https://doi.org/10.1007/s10965-022-03020-7

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