Citation: Cheng Ma, Xiangyu Dou, Zeyu Liu, Peilong Liao, Zhiyang Zhu, Kaerdun Liu, Jianbin Huang. Application and Mechanism of a Novel CO₂-Oil Miscible Flooding Agent, CAA8-X[J]. Acta Physico-Chimica Sinica, ;2022, 38(8): 201201. doi: 10.3866/PKU.WHXB202012019 shu

Application and Mechanism of a Novel CO₂-Oil Miscible Flooding Agent, CAA8-X

Beijing National Laboratory for Molecular Sciences (BNLMS), State Key Laboratory for Structural Chemistry of Unstable and Stable Species, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China

Corresponding author: Jianbin Huang, JBHuang@pku.edu.cn
Received Date: 8 December 2020
Revised Date: 5 January 2021
Accepted Date: 6 January 2021
Available Online: 8 January 2021
Fund Project: the National Oil and Gas Major Project 2016ZX05016-001

Surfactants are widely applied for promoting miscibility and reducing interfacial tension between oil and water phases because of their remarkable amphiphilic morphology. Along with development and popularization of tertiary oil recovery techniques, surfactants play a significant role in crude oil exploitation. Among the various tertiary oil recovery techniques, supercritical CO₂-enhanced oil recovery is a promising method for improving oil recovery. However, the establishment of CO₂-enhanced oil recovery brought new requirements and challenges to traditional surfactant research and development, especially for molecular design. In this method, the reduction of the minimum miscibility pressure between supercritical CO₂ and crude oil is required to achieve miscible flooding—an important means to enhance oil recovery. Therefore, a novel miscible flooding agent that exhibits oil-water miscibility analogous to conventional surfactants is desirable for this method. Meanwhile, a conspicuous difference of polarity matching the high polarity of H₂O molecule against low polarity of alkane molecule, which is the essential feature of traditional surfactant, won't suit this case well due to a medium polarity of CO₂ molecule. According to previous work done in our laboratory, surfactants with multiple ester groups considerably reduce the minimum miscibility pressure between supercritical CO₂ and crude oil. Therefore, inspired by the "oil-water-amphiphilic molecules" design, herein, we replaced the hydrophilic moiety with multiple ester groups and designed a new type of "oil-CO₂ amphiphilic molecule" as a miscible flooding agent, which is composed of an alkane tail and multiple ester groups as the lipophilic and CO₂-philic groups, respectively. In the strategy based on the proposed agent, the number of ester groups and the length of the alkane tail are the main parameters. In addition, we optimized the molecular structure of the proposed agent, CAA8-X, which comprises cetyl and acetyl sucrose esters as the lipophilic and CO₂-philic groups, respectively. We verified that the as-synthesized agent can remarkably reduce the minimum miscibility pressure between supercritical CO₂ and various types of oil samples, including kerosene, white oil, and crude oil from the Changqing region. The crude oil-CO₂ minimum miscibility pressure reduction ratio was 20.5% as measured by the vanishing interfacial tension method and the slim tube test. In this study, we also established a method called the rising height method to measure the minimum miscibility pressure with significantly reduced time and equipment cost. Furthermore, to demonstrate the mechanism of this miscible flooding agent for CO₂-enhanced oil recovery, the affinity between the CO₂-philic group and molecular CO₂ was investigated via molecular dynamics simulation. The results indicated that the "oil-CO₂ amphiphilic molecule" can reduce oil-CO₂ interfacial tension because of lower affinity potential energy between the CO₂-philic group and molecular CO₂.
- Alky sucrose ester,
- Supercritical-CO₂,
- Amphiphile,
- Molecular dynamics,
- Enhanced oil recovery,
- Miscible pressure
1. [1]
  Whorton, L. P.; Brownscombe, E. R. Method for Producing Oil by Means of Carbon Dioxide. U.S. Patent, 2, 623, 596 [P], 1952-12-30.
2. [2]
  Olea, R. A. J. Pet. Sci. Eng. 2015, 129, 23. doi: 10.1016/j.petrol.2015.03.012 doi: 10.1016/j.petrol.2015.03.012
3. [3]
  Azzolina, N. A.; Nakles, D. V.; Gorecki, C. D.; Peck, W. D.; Ayash, S. C.; Melzer, L. S.; Chatterjee, S. Int. J. Greenh. Gas. Control. 2015, 37, 384. doi: 10.1016/j.ijggc.2015.03.037 doi: 10.1016/j.ijggc.2015.03.037
4. [4]
  Hu, W. R. Special Oil and Gas Reservoir, 2007, 14, 1.
5. [5]
  He, J. C.; Liao, G. Z.; Wang, Z. M. J. Southeast Petroleum Univ. 2011, 33 (3), 96. doi: 10.3863/j.issn.1674-5086.2011.03.015
6. [6]
  Yang, Z. G. Chem. Ind. Eng. Prog. 2011, 30 (S1), 420. doi: 10.16085/j.issn.1000-6613.2011.s1.184
7. [7]
  Marcus, Y. Processes 2019, 7 (3), 156. doi: 10.3390/pr7030156 doi: 10.3390/pr7030156
8. [8]
  De Sousa, E. M. B. D.; Toussaint, V. A.; Shariati, A.; Florusse, L. J.; Chiavone, O.; Meireles, M. A. A.; Peters, C. J. Fluid Phase Equilib. 2016, 428 (Suppl.), 32. doi: 10.1016/j.fluid.2016.06.046 doi: 10.1016/j.fluid.2016.06.046
9. [9]
  Sagisaka, M.; Ono, S.; James, C.; Yoshizawa, A.; Mohamed, A.; Guittard, F.; Enick, R. M.; Rogers, S. E.; Czajka, A.; Hill, C.; Eastoe, J. Colloids Surf. B: Biointerfaces 2018, 168, 201. doi: 10.1016/j.colsurfb.2017.12.012 doi: 10.1016/j.colsurfb.2017.12.012
10. [10]
  Mohamed, A.; Ardyani, T.; Sagisaka, M.; Ono, S.; Narumi, T.; Kubota, M.; Brown, P.; James, C.; Eastoe, J.; Kamari, A.; et al. J. Supercritical Fluids 2015, 98, 127. doi: 10.1016/j.supflu.2015.01.012 doi: 10.1016/j.supflu.2015.01.012
11. [11]
  Cummings, S. D.; Enick, R. M.; Rogers, S.; Heenan R.; Eastoe, J. Biochimie 2012, 94, 94. doi: 10.1016/j.biochi.2011.06.021 doi: 10.1016/j.biochi.2011.06.021
12. [12]
  Doherty, M. D.; Lee, J. J.; Dhuwe, A.; O'Brien, M. J.; Perry, R. J.; Beckman, E. J.; Enick, R. M. Energy Fuels 2016, 30, 5601. doi: 10.1021/acs.energyfuels.6b00859 doi: 10.1021/acs.energyfuels.6b00859
13. [13]
  Lee, J. J; Cummings, S. D.; Beckman, E. J.; Enick, R. M.; Burgess, W. A.; Doherty, M. D.; O'Brien, M. J.; Perry, R. J. J. Supercritical Fluids 2017, 119, 17. doi: 10.1016/j.supflu.2016.08.003 doi: 10.1016/j.supflu.2016.08.003
14. [14]
  Luo, T.; Zhang, J. L.; Tan, X. N.; Liu, C. C.; Wu, T. B.; Li, W.; Sang, X. X.; Han, B. X.; Li, Z. H.; Mo, G.; et al. Angew. Chem. Int. Ed. 2016, 55 (43), 13533. doi: 10.1002/anie.201608695 doi: 10.1002/anie.201608695
15. [15]
  Teoh, W. H.; Mammucari, R.; Foster, N. R. J. Organomet. Chem. 2013, 724, 102. doi: 10.1016/j.jorganchem.2012.10.005 doi: 10.1016/j.jorganchem.2012.10.005
16. [16]
  Yang, S. Y.; Lian, L. M.; Yang, Y. Z.; Li, S.; Tang, J.; Ji, Z. M.; Zhang, Y. F. Xinjiang Petrolum Geology 2015, 36 (5), 555. doi: 10.7657/XJPG20150510
17. [17]
  Liu, K. E. D.; Ma, C.; Zhu, Z. Y.; Yang, S. Y.; Lv, W. F.; Yang, Y. Z.; Huang, J. B. Oilfield Chem. 2019, 36 (2), 361. doi: 10.19346/j.cnki.1000-4092.2020.03.026
18. [18]
  Liao, P. L.; Liu, Z. Y.; Liu, K. E. D.; Ma, C.; Zhu, Z. Y.; Yang, S. Y.; Lv, W. F.; Yang, Y. Z.; Huang, J. B. Acta Phys. -Chim. Sin. 2020, 36 (10), 1907034. doi: 10.3866/PKU.WHXB201907034
19. [19]
  Rao, D. N. Fluid Phase Equilibria 1997, 139(1), 311. doi: 10.1016/S0378-3812(97)00180-5 doi: 10.1016/S0378-3812(97)00180-5
20. [20]
  Ayirala, S. C.; Rao, D. N. Comparative Evaluation of a New MMP Determination Technique[C]. SPE 99606, 2006: 1–15.
21. [21]
  Flock, D. L.; Nouar, A. J. Can. Petrol. Tecnol. 1984, 5 (12), 80.
22. [22]
  Zhang, K. Q.; Gu, Y. A. Fuel, 2015, 161, 146. doi: 10.1016/j.fuel.2015.08.039 doi: 10.1016/j.fuel.2015.08.039
23. [23]
  Liu, Z. Y.; Liao, P. L.; Ma, C.; Liu, K. E. D.; Yang, S. Y.; Lv, W. F.; Yang, Y. Z.; Huang, J. B. Oilfield Chem. 2020, 37 (3), 525. doi: 10.19346/j.cnki.1000-4092.2020.03.026
24. [24]
  Chatterjee, D.; Paul, A.; Rajkamal; Yadav, S. RSC Adv. 2015, 5, 29669. doi: 10.1039/c5ra03461b doi: 10.1039/c5ra03461b
25. [25]
  Sun, L. X.; Kiselev, S. B.; Ely, J. F. Fluid Phase Equilibria 2005, 233, 204. doi: 10.1016/j.fluid.2005.04.019 doi: 10.1016/j.fluid.2005.04.019
26. [26]
  Jorgensen, W. L.; Maxwell, D. S.; TiradoRives, J. J. Am. Chem. Soc.; 1996, 118, 11225. doi: 10.1021/ja9621760 doi: 10.1021/ja9621760
27. [27]
  Jorgensen, W. L.; Tirado-Rives, J. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 6665. doi: 10.1073/pnas.0408037102 doi: 10.1073/pnas.0408037102
28. [28]
  Tang, Z. Y.; Zhang, Q.; Yin, Y. D.; Chang, C. E. A. J. Phys. Chem. C 2014, 118, 21589. doi: 10.1021/jp503319s doi: 10.1021/jp503319s
29. [29]
  Shang, J.; Wang, M.; Chen, M.; J. Dai; Zhou, X.; Kuttner, J.; Hilt, G.; Shao, X.; Gottfried, J. M.; Wu, K. Nat. Chem. 2015, 7, 389. doi: 10.1038/NCHEM.2211 doi: 10.1038/NCHEM.2211
30. [30]
  Dodda, L. S.; Vilseck, J. Z.; Tirado-Rives, J.; Jorgensen, W. L. J. Phys. Chem. B 2017, 121, 3864. doi: 10.1021/acs.jpcb.7b00272 doi: 10.1021/acs.jpcb.7b00272
31. [31]
  Rad, H. B.; Sabet, J. K.; Varaminian, F. J. Mol. Liq. 2019, 294, 111636. doi: 10.1016/j.molliq.2019.111636 doi: 10.1016/j.molliq.2019.111636
32. [32]
  Sirk, T. W.; Moore, S.; Brown, E. F. J. Chem. Phys. 2013, 138, 064505. doi: 10.1063/1.4789961 doi: 10.1063/1.4789961
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Application and Mechanism of a Novel CO2-Oil Miscible Flooding Agent, CAA8-X

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Application and Mechanism of a Novel CO₂-Oil Miscible Flooding Agent, CAA8-X