Skip to main content
SpringerLink
Log in

A New Type of Sulfobetaine Surfactant with Double Alkyl Polyoxyethylene Ether Chains for Enhanced Oil Recovery

  • Original Article
  • Published:
Journal of Surfactants and Detergents

Abstract

A new type of sulfobetaine with double alkyl polyoxyethylene (n) ether chains, dicoconut oil alcohol polyoxethylene (n) ether methylhydroxylpropyl sulfobetaine (diC12–14E n HSB) was synthesized using a commercial nonionic surfactant, coconut oil alcohol polyoxethylene (n) ether, as raw material and its properties as a surfactant for enhanced oil recovery (EOR) in the absence of alkali was studied. The purified product is a mixture of homologues with mainly C12/C12, C12/C14 and C14/C14 alkyl chains and widely distributed EO chains (n = 2.2 on average) with an average molar mass of 742.6 g/mol. The diC12–14E2.2HSB has an improved aqueous solubility at 25 °C compared with didodecylmethylhydroxylpropyl sulfobetaine (diC12HSB), a homologue without an EO chain, and is highly surface active as reflected by its low CMC (4.6 × 10−6 mol/L), high saturated adsorption (6.8 × 10−10 mol/cm2) and small cross sectional area (0.24 nm2/molec.) at the air/water interface. With a hydrophile–lipophile balance well matched with Daqing crude oil/connate water system, the sulfobetaine can reduce Daqing crude oil/connate water interfacial tension to ultra-low values at 45 °C in the absence of alkali, and displays a low saturated adsorption at the sandstone/water interface (0.0024 mmol/g), reduced by 69 and 92 % respectively in comparison with that of the corresponding carboxyl betaine, diC12–14E2.2B and its homologue without an EO chain, didodecylmethylcarboxyl betaine (diC12B). With these excellent properties diC12–14E2.2HSB gives a high tertiary recovery, 18.4 % original oil in place, when mixed with other hydrophobic and hydrophilic sulfobetaines in surfactant-polymer (SP) flooding free of alkali. The insertion of EO chains in combination with the replacement of carboxyl betaine by sulfobetaine is therefore very efficient for improving the properties of the double chain hydrophobic carboxyl betaines as surfactants for SP flooding free of alkali.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10

Similar content being viewed by others

References

  1. Taber JJ (1980) Research on enhanced oil recovery: past, present and future. Pure Appl Chem 52:1323–1347

    Article  CAS  Google Scholar 

  2. Babadagli T (2007) Development of mature oil fields—a review. J Pet Sci Eng 57:221–246

    Article  CAS  Google Scholar 

  3. Olajire AA (2014) Review of ASP EOR technology in the petrol industry: prospects and challenges. Energy 77:963–982

    Article  CAS  Google Scholar 

  4. Sheng JJ (2014) A comprehensive review of alkali-surfactant-polymer (ASP) flooding. Asia-Pac J Chem Eng 9:471–489

    CAS  Google Scholar 

  5. Zhu YY, Hou QF, Jian GQ, Ma DS, Wang Z (2013) Current development and application of chemical combination flooding technique. Pet Explor Dev 40(1):96–103

    Article  Google Scholar 

  6. Höök M, Tang X, Pang XQ, Aleklett K (2010) Development journey and outlook of Chinese giant oilfields. Pet Explor Dev 37(2):237–249

    Article  Google Scholar 

  7. Zhu YY, Zhang Y, Niu JL, Liu WD, Hou QF (2012) The research progress in the alkali-free surfactant-polymer combination flooding technique. Pet Explor Dev 39(3):371–376

    Article  Google Scholar 

  8. Bai YR, Xiong CM, Shang XS, Xin YY (2014) Experimental study on ethanolamine/surfactant flooding for enhanced oil recovery. Energy Fuels 28:1829–1837

    Article  CAS  Google Scholar 

  9. Sharma H, Dufour S, Arachchilage GWPP, Weerasooriya U, Pope GA, Mohanty K (2015) Alternative alkalis for ASP flooding in anhydrite containing oil reservoirs. Fuel 140:407–420

    Article  CAS  Google Scholar 

  10. Berger PD, Lee CH (2002) Ultra low concentration surfactants for sandstone and limestone floods, presented at the 2002 SPE/DOE improved oil recovery symposium. Tulsa Oklahoma. SPE 75186

  11. Zhang S, Xu Y, Qiao W, Li Z (2004) Interfacial tensions upon the addition of alcohols to phenylalkane sulfonate monoisomer systems. Fuel 83:2059–2063

    Article  CAS  Google Scholar 

  12. Rosen MJ, Wang H, Shen P, Zhu Y (2005) Ultra low interfacial tension for enhanced oil recovery at very low surfactant concentrations. Langmuir 21:3749–3756

    Article  CAS  Google Scholar 

  13. Xu Z, Li P, Qiao W, Li Z, Cheng L (2006) Effect of aromatic ring in the alkyl chain on surface properties of arylalkyl surfactant solutions. J Surfactants Deterg 9:245–248

    Article  CAS  Google Scholar 

  14. Zhao Z, Liu F, Qiao W, Li Z, Cheng L (2006) Novel alkyl methylnaphthalene sulfonate surfactants: a good candidate for enhanced oil recovery. Fuel 85:1815–1820

    Article  CAS  Google Scholar 

  15. Aoudia M, Al-Shibli MN, Al-Kasimi LH, Al-Maamari R, Al-Bemani A (2006) Novel surfactants for ultra low interfacial tension in a wide range of surfactant concentration and temperature. J Surfactants Deterg 9:287–293

    Article  CAS  Google Scholar 

  16. Iglauer S, Wu Y, Shuler P, Tang Y, Goddard WA III (2009) Alkyl polyglycoside surfactant–alcohol cosolvent formulations for improved oil recovery. Coll Surf A 339:48–59

    Article  CAS  Google Scholar 

  17. Iglauer S, Wu Y, Shuler P, Tang Y, Goddard WA III (2010) New surfactant classes for enhanced oil recovery and their tertiary oil recovery potential. J Pet Sci Eng 71:23–29

    Article  CAS  Google Scholar 

  18. Cui ZG, Song HX, Yu JJ, Jiang JZ, Wang F (2011) Synthesis of N-(3-oxapropanoxyl) dodecanamide and its application in surfactant–polymer flooding. J Surfactants Deterg 14:317–324

    Article  CAS  Google Scholar 

  19. Cui ZG, Du XR, Pei XM, Jiang JZ, Wang F (2012) Synthesis of didodecylmethyl carboxyl betaine and its application in surfactant–polymer flooding. J Surfactants Deterg 15:685–694

    CAS  Google Scholar 

  20. Wu WX, Yan W, Liu CD (2007) The results of core flooding experiment by sulfobetaine/polymer combinational system. Oilfield Chem 24(1):57–62

    Google Scholar 

  21. Xia HF, Wang G, Ma WG, Liu CD, Wang YW (2008) Influence of viscoelasticity and interfacial tension of non-alkali binary compound solution on recovery efficiency of residual oil after water flooding. Acta Pet Ei Sin 29:106–115

    CAS  Google Scholar 

  22. Ma T, Shao HY, Wang HB, Jiang P, Wei TJ, Tang DZ (2008) A laboratory study of the composite two-component oil-displacement system without alkali. China Offshore Oil Gas 20(1):41–47

    Google Scholar 

  23. Zhao JH, Dai CL, Ding QF, Du MY, Feng HS, Wei ZY, Chen A, Zhao MW (2015) The structure effect on the surface and interfacial properties of zwitterionic sulfobetaine surfactants for enhanced oil recovery. RSC Adv 5:13993–14001

    Article  CAS  Google Scholar 

  24. Jiang P, Li N, Ge JJ, Zhang GC, Wang Y, Chen LF, Zhang L (2014) Efficiency of a sulfobetaine-type surfactant on lowering IFT at crude oil–formation water interface. Coll Surf A 443:141–148

    Article  CAS  Google Scholar 

  25. Zhou ZH, Zhang Q, Liu Y, Wang HZ, Cai HY, Zhang F, Tian MZ, Liu ZY, Zhang L (2014) Effect of fatty acids on interfacial tensions of novel sulfobetaines solutions. Energy Fuels 28:1020–1027

    Article  CAS  Google Scholar 

  26. Zhang QQ, Cai BX, Gang HZ, Yang SZ, Mu BZ (2014) A family of novel bio-based zwitterionic surfactants derived from oleic acid. RSC Adv 4:38393–38396

    Article  CAS  Google Scholar 

  27. Berger PD, Lee CH (2002) New anionic alkylaryl surfactants based on olefin sulfonic acids. J Surfactants Deterg 5:39–43

    Article  CAS  Google Scholar 

  28. Lu J, Liyanage PJ, Solairaj S, Adkins S, Arachchilage GP, Kim DH, Britton C, Weerasooriya U, Pope GA (2014) New surfactant developments for chemical enhanced oil recovery. J Pet Sci Eng 120:94–101

    Article  CAS  Google Scholar 

  29. Qiao WH, Cui YC, Zhu YY, Cai HY (2012) Dynamic interfacial tension behaviors between Guerbet betaine surfactants solution and Daqing crude oil. Fuel 102:746–750

    Article  CAS  Google Scholar 

  30. Cui ZG, Wu L, Sun MM, Jiang JZ, Wang F (2011) Synthesis of dodecyllauroyl benzenesulfonate and its application in enhanced oil recovery. Tensides Surf Det 48:408–414

    Article  CAS  Google Scholar 

  31. Cui ZG, Li W, Qi JJ, Wang HJ (2012) Individual and mixed adsorption of alkylcarboxylbetaines and fatty amide ethoxylates at Daqing sandstone/water interface. Coll Surf A 414:180–189

    Article  CAS  Google Scholar 

  32. Cui ZG, Qi D, Song BL, Pei XM, Hu X (2016) Inhibiting hydrophobization of sandstones via adsorption of alkyl carboxyl betaines in SP flooding by using a poly alkylammonium bromides. Energy Fuels 30:2043–2051

    Article  CAS  Google Scholar 

  33. Neustadter EL (1984) In: Tadros TF (ed) Surfactants, chapter 11. Academic Press, London

  34. Rosen MJ, Kunjappu JT (2012) Surfactants and interfacial phenomena, 4th edn, chapter 1. Wiley, Hoboken

  35. Hou LY, Zhang HN, Chen H, Xia QB, Huang DY, Meng L, Liu XF (2014) Synthesis and surface properties of N, N-dimethyl-N-dodecyl polyoxyethylene amine-based surfactants: amine oxide, betaine and sulfobetaine. J Surfactants Deterg 17:403–408

    Article  CAS  Google Scholar 

  36. Song BL, Hu X, Shui XQ, Cui ZG, Wang ZJ (2016) A new type of renewable surfactants for enhanced oil recovery: dialkylpolyoxyethylene ether methyl carboxyl betaines. Coll Surf A 489:433–440

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Fundamental Research Funds for key laboratories of the Ministry of Education (No. JUSRP51507) and for the Central Universities (No. JUSRP51405A) are gratefully acknowledged. Thanks also to the Laboratory of Oil Recovery, Institute of Petroleum Exploring and Development of Daqing, China, for accomplishing oil displacement tests and providing crude oil, connate water, sandstones, as well as PAM for the experiments.

Author information

Authors and Affiliations

  1. The Key Laboratory of Food Colloids and Biotechnology, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, 1800 Lihu Road, Wuxi, 214122, Jiangsu, People’s Republic of China

    Peiqian Li, Cheng Yang, Zhenggang Cui, Binglei Song & Jianzhong Jiang

  2. Solvay (China) Co., Ltd., 3968 Jindu Road, Xinzhuang Industrial Zone, Shanghai, 201108, People’s Republic of China

    Zhijun Wang

Authors
  1. Peiqian Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Cheng Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Zhenggang Cui
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Binglei Song
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Jianzhong Jiang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Zhijun Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Zhenggang Cui.

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Li, P., Yang, C., Cui, Z. et al. A New Type of Sulfobetaine Surfactant with Double Alkyl Polyoxyethylene Ether Chains for Enhanced Oil Recovery. J Surfact Deterg 19, 967–977 (2016). https://doi.org/10.1007/s11743-016-1839-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11743-016-1839-2

Keywords

Search

Navigation