Skip to main content
SpringerLink
Log in

CO2/N2 Triggered Switchable Surfactants with Imidazole Group

  • Original Article
  • Published:
Journal of Surfactants and Detergents

Abstract

In order to overcome the hydrolysis of 2-alkyl-1-hydroxyethyl imidazoline and its unsatisfactory emulsification–demulsification switchability to water-alkane, the long-chain N-alkylimidazole compounds were synthesized by n-octyl bromide, n-decyl bromide, n-dodecyl bromide, n-tetradecyl bromide and n-hexadecyl bromide with imidazole, respectively and characterized by MS, 1H NMR and FTIR. The long-chain N-alkylimidazole compounds can be reversibly transformed into charged surfactants by exposure to CO2. Surface tension values indicated that N-alkylimidazolium bicarbonates had excellent surface activity compared with corresponding conventional surfactants with a lower γ CMC. The surface behaviors of the five surfactants can be illustrated by A min. Five conductivity cycles by bubbling CO2 and N2 alternately indicated that these surfactants could be switched by CO2 reversibly and repeatedly. Emulsions were repeatedly stabilized for five cycles by N-alkylimidazolium bicarbonate and broken by bubbling N2 through the solutions to reverses the reaction, releasing 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
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Minkenberg CB, Florusse RE, Koper GJM, van Esch JH (2009) Triggered self-assembly of simple dynamic covalent surfactants. J Am Chem Soc 131:11274–11275

    Article  CAS  Google Scholar 

  2. Dexter AF, Malcolm AS, Middelberg APJ (2006) Reversible active switching of the mechanical properties of a peptide film at a fluid–fluid interface. Nat Mater 5:502–506

    Article  CAS  Google Scholar 

  3. Dexter AF, Middelberg APJ (2008) Peptides as functional surfactants. Ind Eng Chem Res 47:6391–6398

    Article  CAS  Google Scholar 

  4. Sakai H, Abe M (2005) Control of molecular aggregate formation and solubilization using electro- and photoresponsive surfactant mixtures. In: Abe M, Scamehorn JF (eds) Surfactant science series. Marcel Dekker, New York, pp 507–543

    Google Scholar 

  5. Schmittel M, Lal M, Graf K, Jeschke G, Suske I, Salbeck J (2005) N,N’-Dimethyl-2,3-dialkylpyrazinium salts as redox-switchable surfactants? Redox, spectral, EPR and surfactant properties. Chem Commun 45:5650–5652

    Article  CAS  Google Scholar 

  6. Saji T, Hoshino K, Aoyagui S (1985) Reversible formation and disruption of micelles by control of the redox state of the head group. J Am Chem Soc 107:6865–6868

    Article  CAS  Google Scholar 

  7. Anton P, Koeberle P, Laschewsky A (1992) Structure and properties of zwitterionic polysoaps: functionalization by redox-switchable moieties. Prog Colloid Polym Sci 89:56–59

    Article  CAS  Google Scholar 

  8. Datwani SS, Truskett VN, Rosslee CA, Abbott NL, Stebe KJ (2003) Redox-dependent surface tension and surface phase transitions of a ferrocenyl surfactant: equilibrium and dynamic analyses with fluorescence images. Langmuir 19:8292–8301

    Article  CAS  Google Scholar 

  9. Aydogan N, Abbott NL (2001) Comparison of the surface activity and bulk aggregation of ferrocenyl surfactants with cationic and anionic headgroups. Langmuir 17:5703–5706

    Article  CAS  Google Scholar 

  10. Cheng Z, Ren B, Gao M, Liu X, Tong Z (2007) Ionic self-assembled redox-active polyelectrolyte-ferrocenyl surfactant complexes: mesomorphous structure and electrochemical behavior. Macromolecules 40:7638–7643

    Article  CAS  Google Scholar 

  11. Tsuchiya K, Orihara Y, Kondo Y, Yoshino N, Ohkubo T, Sakai H, Abe M (2004) Control of viscoelasticity using redox reaction. J Am Chem Soc 126:12282–12283

    Article  CAS  Google Scholar 

  12. Ghosh S, Irvin K, Thayumanavan S (2007) Tunable disassembly of micelles using a redox trigger. Langmuir 23:7916–7919

    Article  CAS  Google Scholar 

  13. Sakai H, Matsumura A, Yokoyama S, Saji T, Abe M (1999) Photochemical switching of vesicle formation using an azobenzene-modified surfactant. J Phys Chem. B 103:10737–10740

    Article  CAS  Google Scholar 

  14. Liu Y, Jessop PG, Cunningham M, Eckert CA, Liotta CL (2006) Switchable surfactants. Science 313:958–960

    Article  CAS  Google Scholar 

  15. Qin Y, Yang H, Ji J, Yao S, Kong Y, Wang Y (2009) Reversible performance of dodecyl tetramethyl guanidine solution induced by co2 trigger. Tenside Surf Deterg 46:294–297

    Article  CAS  Google Scholar 

  16. Jessop PG, Heldebrant DJ, Li X, Eckert CA, Liotta CL (2005) Reversible nonpolar-to-polar solvent. Nature 436:1102

    Article  CAS  Google Scholar 

  17. Phan L, Chiu D, Heldebrant DJ, Huttenhower H, John E, Li XW, Pollet P, Wang RY, Eckert CA, Liotta CL, Jessop PG (2008) Switchable solvents consisting of amidine/alcohol or guanidine/alcohol mixtures. Ind Eng Chem Res 47:539–545

    Article  CAS  Google Scholar 

  18. Phan L, Jessop PG (2009) Switching the hydrophilicity of a solute. Green Chem 11:307–308

    Article  CAS  Google Scholar 

  19. Jessop PG, Phan L, Carrier A, Robinson S, Durr CJ, Harjani JR (2010) A solvent having switchable hydrophilicity. Green Chem 12:809–814

    Article  CAS  Google Scholar 

  20. Heldebrant DJ, Koech PK, Ang MC, Liang C, Rainbolt JE, Yonker CR, Jessop PG (2010) Reversible zwitterionic liquids, the reaction of alkanol guanidines, alkanol amidines and diamines with CO2. Green Chem 12:713–721

    Article  CAS  Google Scholar 

  21. Yamada T, Lukac PJ, George M, Weiss RG (2007) Reversible, room-temperature ionic liquids. Amidinium carbamates derived from amidines and aliphatic primary amines with carbon dioxide. Chem Mater 19:967–969

    Article  CAS  Google Scholar 

  22. Weihong Qiao, Zhibo Zheng, Qingzhao Shi (2012) Synthesis and properties of a series of CO2 switchable surfactants with Imidazoline group. J Surf Deterg 15:533–539

    Article  CAS  Google Scholar 

  23. Durán-Valle CJ, Madrigal-Martínez M, Martínez-Gallego M, Fonseca IM, Matos I, BotelhodoRego AM (2012) Activated carbon as a catalyst for the synthesis of N-alkylimidazoles and imidazolium ionic liquids. Catal Today 187:108–114

    Article  CAS  Google Scholar 

  24. Calvino-Casilda V, Martín-Aranda RM, López-Peinado AJ, Bejblová M, Čejka J (2008) Sonocatalysis and zeolites: an efficient route to prepare N-alkylimidazoles. Appl Catal A 338:130–135

    Article  CAS  Google Scholar 

  25. Khabnadideh S, Rezaei Z, Khalafi-Nezhad A, Bahrinajafi R, Mohamadi R, Farrokhroz AA (2003) Synthesis of N-Alkylated derivatives of imidazole as antibacterial agents. Bioorg Med Chem Lett 13:2863–2865

    Article  CAS  Google Scholar 

  26. Cuevas-Yañez E, Serrano JM, Huerta G, Muchowski JM, Cruz-Almanza R (2004) Copper carbenoid mediated N-alkylation of imidazoles and its use in a novel synthesis of bifonazole. Tetrahedron 60:9391–9396

    Article  CAS  Google Scholar 

  27. Kim EJ, Ko SY, Dziadulewicz EK (2005) Mitsunobu alkylation of imidazole: a convenient route to chiral ionic liquids. Tetrahedron Lett 46:631–633

    Article  CAS  Google Scholar 

  28. Xixin Wang, Ruzhong Sun (2003) Synthesis and property study on N-alkyl imidazole hydrochloride. Chem Res Appl 15:726–727

    Google Scholar 

  29. Xiao JX, Zhao ZG (2003) Principles of surfactants. Chemical Industry Press, Beijing

    Google Scholar 

  30. Xie Z, Feng Y (2010) Synthesis and properties of alkylbetaine zwitterionic gemini surfactants. J Surf Deterg 13:51–57

    Article  CAS  Google Scholar 

  31. Qiao Weihong, Zheng Zhibo, Peng Huan (2011) Synthesis of switchable amphipathic molecules triggered by CO2 through carbonyl-amine condensation. Eur J Lipid Sci Technol 113:841–847

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the PetroChina Daqing Oilfield Co., Ltd.

Author information

Authors and Affiliations

  1. State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian, 116024, People’s Republic of China

    Mingfeng Chai, Zhibo Zheng, Lei Bao & Weihong Qiao

Authors
  1. Mingfeng Chai
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zhibo Zheng
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Lei Bao
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Weihong Qiao
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Weihong Qiao.

About this article

Cite this article

Chai, M., Zheng, Z., Bao, L. et al. CO2/N2 Triggered Switchable Surfactants with Imidazole Group. J Surfact Deterg 17, 383–390 (2014). https://doi.org/10.1007/s11743-014-1569-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11743-014-1569-2

Keywords

Search

Navigation