Two new ammonium-based poly(ionic liquid)s for breaking water-in-crude oil emulsions

References

• Wong, S.; Lim, J.; Dol, S. Crude Oil Emulsion: A Review on Formation, Classification and Stability of Water-In-Oil Emulsions. J. Pet. Sci. Eng. 2015, 135, 498–504. DOI: 10.1016/j.petrol.2015.10.006.
   Web of Science ®Google Scholar
• Kokal, S. Crude-Oil Emulsions: A State-Of-The-Art Review. SPE. Prod. & Facil. 2005, 20(1), 5–13. DOI: 10.2118/77497-PA.
   Web of Science ®Google Scholar
• Nour, A. H. Emulsion Types, Stability Mechanisms and Rheology: A Review. Int. J. Innov. Res. Sci. Stud. 2018, 1(1), 14–21. DOI: 10.53894/ijirss.v1i1.4.
   Google Scholar
• Alwadani, M. S. Characterization and rheology of water-in-oil emulsion from deepwater fields;Rice University, Master thesis, 2010.
   Google Scholar
• Umar, A. A.; Saaid, I. B. M.; Sulaimon, A. A.; Pilus, R. B. M. A Review of Petroleum Emulsions and Recent Progress on Water-In-Crude Oil Emulsions Stabilized by Natural Surfactants and Solids. J. Pet. Sci. Eng. 2018, 165, 673–690. DOI: 10.1016/j.petrol.2018.03.014.
   Web of Science ®Google Scholar
• Raya, S. A.; Mohd Saaid, I.; Abbas Ahmed, A.; Abubakar Umar, A. A Critical Review of Development and Demulsification Mechanisms of Crude Oil Emulsion in the Petroleum Industry. J. Pet. Explor. Prod. Technol. 2020, 10(4), 1711–1728. DOI: 10.1007/s13202-020-00830-7.
   Web of Science ®Google Scholar
• Ma, J.; Yang, Y.; Li, X.; Sui, H.; He, L. Mechanisms on the Stability and Instability of Water-In-Oil Emulsion Stabilized by Interfacially Active Asphaltenes: Role of Hydrogen Bonding Reconstructing. Fuel. 2021, 297, 120763. DOI: 10.1016/j.fuel.2021.120763.
   Web of Science ®Google Scholar
• Liu, J.; Zhang, Y.; Peng, K.; Zhao, X.; Xiong, Y.; Huang, X. A Review of the Interfacial Stability Mechanism of Aging Oily Sludge: Heavy Components, Inorganic Particles, and Their Synergism. J. Hazard. Mater. 2021, 415, 125624. DOI: 10.1016/j.jhazmat.2021.125624.
   PubMed Web of Science ®Google Scholar
• Abdulredha, M. M.; Hussain, S. A.; Abdullah, L. C. Optimization of the Demulsification of Water in Oil Emulsion via Non-Ionic Surfactant by the Response Surface Methods. J. Pet. Sci. Eng. 2020, 184, 106463. DOI: 10.1016/j.petrol.2019.106463.
   Web of Science ®Google Scholar
• Feng, X.; Behles, J. A. Understanding the Demulsification of Water-In-Diluted Bitumen Froth Emulsions. Energy. Fuels. 2015, 29(7), 4616–4623. DOI: 10.1021/acs.energyfuels.5b00798.
   Web of Science ®Google Scholar
• Groysman, A. Corrosion Problems and Solutions in Oil Refining and Petrochemical Industry; Springer: 2017. DOI: 10.1007/978-3-319-45256-2.
   Google Scholar
• Faqihi, N. A.; Abdullah, M. M.; Al‐Lohedan, H. A.; Almarhoon, Z. M.; Mohammad, F. Synthesis, Characterization, and Application of Two New Ionic Liquids for the Dehydration of Heavy Crude Oil Emulsions. J. Mol. Liq. 2022, 358, 119202. DOI: 10.1016/j.molliq.2022.119202.
   Web of Science ®Google Scholar
• Fuentes, J. V.; Zamora, E. B.; Chakraborty, A.; Zavala, G.; Xu, Z.; McCaffrey, W.; Li, Z.; Vázquez, F.; Flores, C. A. A Critical Evaluation of Novel Demulsifying Agents Based on Acrylic Terpolymers for Mexican Heavy Crude Oils Dehydration. Sep. Purif. Technol. 2022, 281, 119878. DOI: 10.1016/j.seppur.2021.119878.
   Web of Science ®Google Scholar
• Shah Buddin, M. M. H.; Ahmad, A. L.; Abd Khalil, A. T.; Puasa, S. W. A Review of Demulsification Technique and Mechanism for Emulsion Liquid Membrane Applications. J Dispers. Sci. Technol. 2022, 43(6), 910–927. DOI: 10.1080/01932691.2020.1845962.
   Web of Science ®Google Scholar
• Yi, M.; Huang, J.; Wang, L. Research on Crude Oil Demulsification Using the Combined Method of Ultrasound and Chemical Demulsifier. J. Chem. 2017, 2017, 1–7. DOI: 10.1155/2017/9147926.
   Web of Science ®Google Scholar
• Sadatshojaie, A.; Wood, D. A.; Jokar, S. M.; Rahimpour, M. R. Applying Ultrasonic Fields to Separate Water Contained in Medium-Gravity Crude Oil Emulsions and Determining Crude Oil Adhesion Coefficients. Ultrason Sonochem. 2021, 70, 105303. DOI: 10.1016/j.ultsonch.2020.105303.
   PubMed Web of Science ®Google Scholar
• Yonguep, E.; Chowdhury, M. Optimization of the Demulsification Response Surface Methodology. S. Afr. J. Chem. Eng. 2021, 36(1), 105–117. DOI: 10.1016/j.sajce.2021.02.002.
   Google Scholar
• Peng, J.; Liu, Q.; Xu, Z.; Masliyah, J. Novel Magnetic Demulsifier for Water Removal from Diluted Bitumen Emulsion. Energy. Fuels. 2012, 26(5), 2705–2710. DOI: 10.1021/ef2014259.
   Web of Science ®Google Scholar
• Issaka, S. A.; Nour, A. H.; Yunus, R. M. Review on the Fundamental Aspects of Petroleum Oil Emulsions and Techniques of Demulsification. J. pet. environ. biotechnol. 2015, 6(2), 1. 2021. DOI:10.4172/2157-7463.1000214.
   Google Scholar
• Alsabagh, A.; Hassan, M.; Desouky, S.; Nasser, N.; Elsharaky, E.; Abdelhamid, M. Demulsification of W/O Emulsion at Petroleum Field and Reservoir Conditions Using Some Demulsifiers Based on Polyethylene and Propylene Oxides. Egypt. J. Pet. 2016, 25(4), 585–595. DOI: 10.1016/j.ejpe.2016.05.008.
   Google Scholar
• Abdulkadir, M. Comparative Analysis of the Effect of Demulsifiers in the Treatment of Crude Oil Emulsion. ARPN J. Eng. Appl. Sci. 2010, 5(6), 67–73.
   Google Scholar
• Shehzad, F.; Hussein, I. A.; Kamal, M. S.; Ahmad, W.; Sultan, A. S.; Nasser, M. S. Polymeric Surfactants and Emerging Alternatives Used in the Demulsification of Produced Water: A Review. Polym. Rev. 2018, 58(1), 63–101. DOI: 10.1080/15583724.2.017.1340308.
   Web of Science ®Google Scholar
• Faisal, W.; Almomani, F. A Critical Review of the Development and Demulsification Processes Applied for Oil Recovery from Oil in Water Emulsions. Chemosphere. 2021, 291, 133099. DOI: 10.1016/j.chemosphere.2021.133099.
   PubMed Web of Science ®Google Scholar
• Ezzat, A. O.; Atta, A. M.; Al-Lohedan, H. A.; Abdullah, M. M.; Hashem, A. I. Synthesis and Application of Poly (Ionic Liquid) Based on Cardanol as Demulsifier for Heavy Crude Oil Water Emulsions. Energy. Fuels. 2018, 32(1), 214–225. DOI: 10.1021/acs.energyfuels.7b02955.
   Web of Science ®Google Scholar
• Hassanshahi, N.; Hu, G.; Li, J. Application of Ionic Liquids for Chemical Demulsification: A Review. Molecules. 2020, 25(21), 4915. DOI: 10.3390/molecules25214915.
   PubMed Web of Science ®Google Scholar
• Ezzat, A. O.; Al-Lohedan, H. A. Dehydration of Heavy Crude Oil Emulsions Using Novel Imidazolium-Based Poly Ionic Liquids. J. Mol. Liq. 2021, 326, 115284. DOI: 10.1016/j.molliq.2021.115284.
   Web of Science ®Google Scholar
• Zhang, J.; Chen, Z.; Zhang, Y.; Dong, S.; Chen, Y.; Zhang, S. Poly(ionic Liquid)s Containing Alkoxy Chains and Bis (Trifluoromethanesulfonyl) Imide Anions as Highly Adhesive Materials. Adv. Mater. 2021, 33(30), 2100962. DOI: 10.1002/adma.202100962.
   Web of Science ®Google Scholar
• Niu, H.; Wang, L.; Guan, P.; Zhang, N.; Yan, C.; Ding, M.; Guo, X.; Huang, T.; Hu, X. Recent Advances in Application of Ionic Liquids in Electrolyte of Lithium Ion Batteries. J. Energy Storage. 2021, 40, 102659. DOI: 10.1016/j.est.2021.102659.
   Web of Science ®Google Scholar
• Zhang, S.-Y.; Zhuang, Q.; Zhang, M.; Wang, H.; Gao, Z.; Sun, J.-K.; Yuan, J. Poly (Ionic Liquid) Composites. Chem. Soc. Rev. 2020, 49(6), 1726–1755. DOI: 10.1039/C8CS00938D.
   PubMed Web of Science ®Google Scholar
• Yan, X.; Anguille, S.; Bendahan, M.; Moulin, P. Ionic Liquids Combined with Membrane Separation Processes: A Review. Sep. Purif. Technol. 2019, 222, 230–253. DOI: 10.1016/j.seppur.2019.03.103.
   Web of Science ®Google Scholar
• Atta, A. M.; Al-Lohedan, H. A.; Ezzat, A. O. Synthesis and Application of Geminal Dicationic Ionic Liquids and Poly (Ionic Liquids) Combined Imidazolium and Pyridinium Cations as Demulsifiers for Petroleum Crude Oil Saline Water Emulsions. J. Mol. Liq. 2021, 325, 115264. DOI: 10.1016/j.molliq.2020.115264.
   Web of Science ®Google Scholar
• Ezzat, A. O.; Atta, A. M.; Al-Lohedan, H. A.; Hashem, A. I. Synthesis and Application of New Surface Active Poly (Ionic Liquids) Based on 1, 3-Dialkylimidazolium as Demulsifiers for Heavy Petroleum Crude Oil Emulsions. J. Mol. Liq. 2018, 251, 201–211. DOI: 10.1016/j.molliq.2017.12.081.
   Web of Science ®Google Scholar
• Abdullah, M. M.; Al-Lohedan, H. A. Alginate-Based Poly Ionic Liquids for the Efficient Demulsification of Water in Heavy Crude Oil Emulsions. Fuel. 2022, 320, 123949. DOI: 10.1016/j.fuel.2022.123949.
   Web of Science ®Google Scholar
• Atta, A. M.; Al-Lohedan, H. A.; Abdullah, M. M. Dipoles Poly (Ionic Liquids) Based on 2-Acrylamido-2-Methylpropane Sulfonic Acid-Co-Hydroxyethyl Methacrylate for Demulsification of Crude Oil Water Emulsions. J. Mol. Liq. 2016, 222, 680–690. DOI: 10.1016/j.molliq.2016.07.114.
   Web of Science ®Google Scholar
• Abdullah, M. M.; Al-Lohedan, H. A. Demulsification of Water in Heavy Crude Oil Emulsion Using a New Amphiphilic Ionic Liquid Based on the Glycolysis of Polyethylene Terephthalate Waste. J. Mol. Liq. 2020, 307, 112928. DOI: 10.1016/j.molliq.2020.112928.
   Web of Science ®Google Scholar
• Zolfaghari, R.; Fakhru’l-Razi, A.; Abdullah, L. C.; Elnashaie, S. S.; Pendashteh, A. Demulsification Techniques of Water-In-Oil and Oil-In-Water Emulsions in Petroleum Industry. Sep. Purif. Technol. 2016, 170, 377–407. DOI: 10.1016/j.seppur.2016.06.026.
   Web of Science ®Google Scholar
• Capek, I. Degradation of Kinetically-Stable O/W Emulsions. Adv. Colloid Interface Sci. 2004, 107(2–3), 125–155. DOI: 10.1016/S0001-8686(03)00115-5.
   PubMed Web of Science ®Google Scholar
• Zaki, N. N.; Abdel-Raouf, M. E.; Abdel-Azim, A.-A. Propylene Oxide-Ethylene Oxide Block Copolymers as Demulsifiers for Water-In-Oil Emulsions, Effect of Molecular Weight and Hydrophilic-Lipophylic Balance on the Demulsification Efficiency. Monatsh. Chem. 1996, 127(6–7), 621–629. DOI: 10.1007/BF00817254.
   Web of Science ®Google Scholar
• Roshan, N.; Ghader, S.; Rahimpour, M. R. Application of the Response Surface Methodology for Modeling Demulsification of Crude Oil Emulsion Using a Demulsifier. J Dispers. Sci. Technol. 2018, 39(5), 700–710. 2016. DOI:10.1080/01932691.2017.1385480.
   Web of Science ®Google Scholar
• Abdulraheim, A. M. Green Polymeric Surface Active Agents for Crude Oil Demulsification. J. Mol. Liq. 2018, 271, 329–341. DOI: 10.1016/j.molliq.2018.08.153.
   Web of Science ®Google Scholar
• Abdullah, M.; Sajid Ali, M.; Al-Lohedan, H. A. Application of New Ammonium-Based Ionic Liquids for Dehydration of Crude Oil Emulsions. J. Chem. 2023, 2023, 1–12. DOI: 10.1155/2023/8711570.
   Web of Science ®Google Scholar