Advertisement

Research on Chemical Intermediates

, Volume 41, Issue 4, pp 1935–1950 | Cite as

Synthesis of a novel cationic asphalt emulsifier and its investigation by online FTIR spectrophotometry

  • Na Li
  • Laishun Shi
  • Xuli Gong
  • Qiyan Xu
  • Xin Liu
  • Xiaolong Wang
Article

Abstract

A novel cationic asphalt emulsifier N,N-dimethyl-N-(oxiran-2-ylmethyl)octadecan-1-aminium chloride was synthesized by reaction of epichlorohydrin and N,N-dimethyloctadecylamine. The optimum reaction condition was obtained. The yield and epoxy group value reached 98.0 and 41.8 %, respectively, at the optimum conditions: reaction temperature of 50 °C, reaction time of 5 h, and feedstock mole ratio of epichlorohydrin to N,N-dimethyloctadecylamine of 1.2. The chemical structure of the emulsifier was confirmed by Fourier-transform infrared (FTIR), 1H nuclear magnetic resonance (NMR), and elemental analysis. The synthesis process was monitored by the online FTIR technique. The by-product was detected by online FTIR analysis. Based upon the experimental data, a plausible reaction mechanism is proposed for the reaction. The critical micelle concentration (CMC) of the emulsifier has a lower value of 4.35 × 10−4 mol/L. The surface tension at CMC is 28.51 mN/m. The emulsifier exhibits satisfactory emulsification. The prepared bituminous emulsion showed higher storage stability. The emulsifier belongs to the class of medium-set asphalt emulsifiers.

Keywords

Asphalt Emulsifier Cationic Synthesis Online FTIR 

Notes

Acknowledgments

The authors would like to thank the Shandong Provincial Science and Technology Project (no. 2012GGX10708) for financial support.

References

  1. 1.
    K. Takamura, A. Burghart, W. Kirk, U.S. Patent 20100047015, 25 Feb 2010Google Scholar
  2. 2.
    S.P. Kleiger, L. Tarlini, U.S. Patent 7993441, 9 Aug 2011Google Scholar
  3. 3.
    J.B. Llosas, R. Valls, S. Merlet, J. Molitor, U.S. Patent 8197588, 12 Jun 2012Google Scholar
  4. 4.
    W.R. Knight, G. Wang, D.R. Cremona, R.M. Velichka, U.S. Patent 20120157597, 21 Jun 2012Google Scholar
  5. 5.
    H.H. Moorer, U.S. Patent 4088505, 9 May 1978Google Scholar
  6. 6.
    W.T. Zdybak, U.S. Patent 4427449, 24 Jan 1984Google Scholar
  7. 7.
    M.W. Shuey, R.S. Custer, U.S. Patent 5650000, 22 Jul 1997Google Scholar
  8. 8.
    D.F. Levy, D.W. Gagle, U.S. Patent 3093595, 11 Jun 1963Google Scholar
  9. 9.
    P.E. Graf, S.J. Agazzi, E.J. Vanderzanden, U.S. Patent 4985079, 15 Jan 1991Google Scholar
  10. 10.
    A.M. Vivoni, A.A. Rodrigues, U.S. Patent 20100267865, 21 Oct 2010Google Scholar
  11. 11.
    Y. Honma, R. Tamaki, H. Sasaki, U.S. Patent 6840991, 11 Jan 2005Google Scholar
  12. 12.
    G.G.I. Moore, M.S. Terrazas, U.S. Patent 7164041, 16 Jan 2007Google Scholar
  13. 13.
    D.J. Tracy, R. Li, M.S. Dahanayake, J. Yang, U.S. Patent 6204297, 20 Mar 2001Google Scholar
  14. 14.
    ø. Rist, A. Rike, L. Ljones, P.H.J. Carlsen, Molecules 6, 979–987 (2001)CrossRefGoogle Scholar
  15. 15.
    M.M. Velázquez, F. Ortega, F. Monroy, R.G. Rubio, S. Pegiadou, L. Pérez, M.R. Infante, J. Colloid Interface Sci. 283, 144–152 (2005)CrossRefGoogle Scholar
  16. 16.
    T. Iwasaki, M. Ogawa, K. Esumi, K. Meguro, Langmuir 7, 30–35 (1991)CrossRefGoogle Scholar
  17. 17.
    S. Ghosh, D. Khatua, J. Dey, Langmuir 27, 5184–5192 (2011)CrossRefGoogle Scholar
  18. 18.
    J.L. Bigorra, N.B. Gilabert, M.O. Hernandez, X.C. Cruxens, R.P. Subirana, U.S. Patent 6015780, 18 Jan 2000Google Scholar
  19. 19.
    J.M. González, M.J. Bermejo, R.M. Barceló, J. Vilaret, N. Siscart, U.S. Patent 6683033, 27 Jan 2004Google Scholar
  20. 20.
    J. Martin, J.M. Hemsley, U.S. Patent 8167993, 1 May 2012Google Scholar
  21. 21.
    K. Isobe, R.Tamaki, U.S. Patent 6114418, 5 Sept 2000Google Scholar
  22. 22.
    C. Huai, L. Shi, N. Li, Res. Chem. Intermed. 39, 597–614 (2013)CrossRefGoogle Scholar
  23. 23.
    L. Shi, Z. Wan, L. Wang, Y. Xue, J. Shandong Univ. (Eng. Sci.) 37, 122–126 (2007)Google Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2013

Authors and Affiliations

  • Na Li
    • 1
  • Laishun Shi
    • 1
  • Xuli Gong
    • 1
  • Qiyan Xu
    • 1
  • Xin Liu
    • 1
  • Xiaolong Wang
    • 1
  1. 1.School of Chemistry and Chemical EngineeringShandong UniversityJinanPeople’s Republic of China

Personalised recommendations