Skip to main content
SpringerLink
Log in

Synthesis and Performance Evaluation of CO2/N2 Switchable Tertiary Amine Gemini Surfactant

  • Short Communication
  • Published:
Journal of Surfactants and Detergents

Abstract

A type of switchable tertiary amine Gemini surfactant, N,N′-di(N,N-dimethyl propylamine)-N,N′-didodecyl ethylenediamine, was synthesized by two substitution reactions with 3-chloro-1-(N,N-dimethyl) propylamine, bromododecane and ethylene diamine as main raw materials. The structure of the product was characterized by FTIR and 1H-NMR. We also investigated the surface tension when CO2 was bubbled in different concentrations of surfactant solution and the influence of different CO2 volumes on surface tension under a constant surfactant concentration. Finally the surface tension curve and the related parameters were acquired by surface tension measurements. The experimental results showed that the structure of the synthesized compounds were in conformity with the expected structure of the surfactant, and displayed a better surface activity after bubbling CO2. The critical micelle concentration (CMC) surface tension at CMC (γ cmc) pC20 (negative logarithm of the surfactant’s molar concentration C20, required to reduce the surface tension by 20 mN/m) surface excess (Γ max) at air/solution interface and the minimum area per surfactant molecule at the air/solution interface (A min) were determined. Results indicate that the target product had good surface activity after bubbling CO2.

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
Scheme 2
Scheme 3
Scheme 4
Scheme 5
Fig. 1
Fig. 2
Fig. 3
Fig. 4

References

  1. Chu Z, Feng Y. Thermo-switchable surfactant gel. Chem Commun. 2011;47(25):7191–3.

    Article  CAS  Google Scholar 

  2. Zhang Y, Han Y, Chu Z, He S, Zhang J, Feng Y. Thermally induced structural transitions from fluids to hydrogels with pH-switchable anionic wormlike micelles. J Colloid Interface Sci. 2013;394:319–28.

    Article  CAS  Google Scholar 

  3. Davies TS, Ketner AM, Raghavan SR. Self-Assembly of surfactant vesicles that transform into viscoelastic wormlike micelles upon heating. J Am Chem Soc. 2006;128(20):6669–75.

    Article  CAS  Google Scholar 

  4. Shi H, Wang Y, Fang B, Talmon Y, Ge W, Raghavan SR, Zakin JL. Light-responsive threadlike micelles as drag reducing fluids with enhanced heat-transfer capabilities. Langmuir. 2011;27(10):5806–13.

    Article  CAS  Google Scholar 

  5. Lahann J, Mitragotri S, Tran TN, Kaido H, Sundaram J, Choi IS, Hoffer S, Somorjai GA, Langer R. A reversibly switching surface. Science. 2003;299(5605):371–4.

    Article  CAS  Google Scholar 

  6. Iwatani M, Kudo K, Sugita N, et al. Kinetics on the carboxylation of cyclohexanone in dimethyl sulfoxide solution containing 1,8-diazabicyclo [5,4,0] undec-7-ene and carbon dioxide. Sekiyu Gakkaishi. 1978;21(5):290–96.

    Article  CAS  Google Scholar 

  7. Jessop PG, Heldebrant DJ, Li XW, Eckert CA, Liotta CL. Reversible nonpolar-to-polar solvent. Nature. 2005;436:1102.

    Article  CAS  Google Scholar 

  8. Chen L, Harjani JR, Robert T, Rogel E, Kuehne D, Ovalles C, Sampath V, Jessop PG. Use of CO2-triggered switchable surfactants for the stabilization of oil-in-water emulsions. Energy Fuels. 2012;26(1):488–94.

    Article  Google Scholar 

  9. Qin Y, Yang H, Ji J, Yao S, Kong Y, Wang Y. Reversible performance of dodecyl tetramethyl guanidine solution induced by CO2 trigger. Tenside Surfactants Deterg. 2009;46(5):294–7.

    Article  CAS  Google Scholar 

  10. Lu HS, He Y, Huang ZY. Foaming Properties of CO2-triggered surfactants for switchable foam control. J Dispers Sci Technol. 2014;35(6):832–9.

    Article  CAS  Google Scholar 

  11. Han D, Tong X, Boissière O, Zhao Y. General strategy for making CO2-switchable polymers. ACS Macro Lett. 2012;1(1):57–61.

    Article  CAS  Google Scholar 

  12. Han D, Boissière O, Kumar S, Tong X, Tremblay L, Zhao Y. Two-Way CO2-switchable triblock copolymer hydrogels. Macromolecules. 2012;45(18):7440–5.

    Article  CAS  Google Scholar 

  13. Holland A, Wechsler D, Patel A, Molloy BM, Boyd AR, Jessop PG. Separation of bitumen from oil sands using a switchable hydrophilicity solvent. Can J Chem. 2012;90(10):805–10.

    Article  CAS  Google Scholar 

  14. Su X, Cunningham MF, Jessop PG. Switchable viscosity triggered by CO2 using smart worm-like micelles. Chem Commun. 2013;49(26):2655–7.

    Article  CAS  Google Scholar 

  15. Zhou M, Zhao JZ, Wang X, Jing J, Zhou L. Synthesis and characterization of novel Surfactants 1,2,3-tri(2-oxypropylsulfonate-3-alkylether-propoxy) propanes. J Surfactants Deterg. 2013;16(5):665–72.

    Article  CAS  Google Scholar 

  16. Zhou M, Xia L, He Y, Zhang L, Qiao X, Zhong X. Synthesis of new Salt-Resistant sulfonate Gemini surfactants with hydroxyl groups. J Surfactants Deterg. 2015;18(2):303–8.

    Article  CAS  Google Scholar 

  17. Lu HS, Guan XQ, Dai SS, Huang ZH. Application of CO2-Triggered switchable surfactants to form emulsion with xinjiang heavy oil. J Dispers Sci Technol. 2014;35(5):655–62.

    Article  Google Scholar 

  18. Lu H, He Y, Huang ZY. Synthesis and properties of a series of CO2 switchable Gemini imidazolium surfactants. Tenside Surfactants Deterg. 2014;51(5):415–20.

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors would like to thank the National Natural Science Foundation of China (No. 51274210) for financial support. This research was also supported by Project of Sichuan Province College Key Laboratory of Oil and Gas Field Materials (No. X151516KCL33).

Author information

Authors and Affiliations

  1. School of Materials Science and Engineering, Southwest Petroleum University, Chengdu, 610500, China

    Ming Zhou, Gang Wang, Yaoyang Xu, Ze Zhang, Sisi Li, Buhua Hu & Yunlong Zhao

  2. State Key Laboratory of Oil and Gas Reservoir Geology and Exploitation, School of Materials Science and Engineering, Southwest Petroleum University, Chengdu, 610500, Sichuan, China

    Ming Zhou, Yaoyang Xu, Ze Zhang, Sisi Li, Buhua Hu & Yunlong Zhao

Authors
  1. Ming Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Gang Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yaoyang Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ze Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Sisi Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Buhua Hu
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Yunlong Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ming Zhou.

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhou, M., Wang, G., Xu, Y. et al. Synthesis and Performance Evaluation of CO2/N2 Switchable Tertiary Amine Gemini Surfactant. J Surfact Deterg 20, 1483–1489 (2017). https://doi.org/10.1007/s11743-017-2019-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11743-017-2019-8

Keywords

Search

Navigation