Home Synthesis and Properties of a Novel Gemini Surfactant with Bis-piperidinium
Article
Licensed
Unlicensed Requires Authentication

Synthesis and Properties of a Novel Gemini Surfactant with Bis-piperidinium

  • Yicheng Xie , Jiajia Liu , Fan Liu and Hujun Xu
Published/Copyright: September 6, 2017
Become an author with De Gruyter Brill

Abstract

A novel cationic Gemini surfactant with bis-piperidinium and benzene ring (C10-CGP) was synthesized by aniline, epichlorohydrin and 1-bromodecane in three steps. The structure of C10-CGP was characterized by mass spectroscopy (MS) and nuclear magnetic resonance (1H NMR). The critical micelle concentration (CMC) and the corresponding surface tension (γCMC) of C10-CGP were measured from 298 K to 313 K and the thermodynamic parameters of the micellization were calculated. The results showed that the critical micelle concentration (CMC) and γCMC were 0.976 × 10−3 mol · L−1 and 28.93 mN · m−1 at 298 K, respectively. With the temperature increase, the CMC increased, the maximum surface adsorption capacity (Γmax) decreased, the γCMC decreased and the minimum molecule area (Amin) increased. The free energy of the system during the micelle formation was negative. When the Gemini surfactant was used as an asphalt emulsifier, C10-CGP exhibited good a emulsifying ability. C10-CGP is a slow-set asphalt emulsifier.

Kurzfassung

Ein neues kationisches Gemini-Tensid mit Bis-Piperidinium- und Benzolring (C10-CGP) wurde mittels Anilin, Epichlorhydrin und 1-Bromdecan in drei Reaktionsschritten synthetisiert. Die Struktur von C10-CGP wurde durch Massenspektroskopie (MS) und Kernmagnetresonanz (1H-NMR) charakterisiert. Die kritische Mizellenkonzentration (CMC) und die entsprechende Oberflächenspannung (γCMC) von C10-CGP wurden zwischen 298 K bis 313 K gemessen und die thermodynamischen Parameter der Mizellenbildung berechnet. Die Ergebnisse zeigten, dass die kritische Mizellenbildungskonzentration (CMC) und die Oberflächenspannung bei der CMC (γCMC) bei 298 K 28.93 mN · m−1 bzw. 0,976 × 10 mol L−1 betrugen. Mit Temperaturerhöhung nahm die CMC zu, die maximale Oberflächenadsorptionskapazität (Γmax) sank, die Oberflächenspannung bei der CMC (γCMC) sank und der minimale Platzbedarf pro Molekül (Amin) nahm zu. Die freie Energie des Systems während der Mizellenbildung war negativ. Bei Verwendung des Gemini-Tensids als Asphalt-Emulgator, zeigte C10-CGP eine gute Emulgierfähigkeit. C10-CGP ist ein langsam wirkender Asphalt-Emulgator.


*Correspondence address, Dr. Hujun Xu, Jiangnan University, School of Chemical and Material Engineering, Lihu Avenue, Wuxi 214122, P. R. China, Tel.: +86-13706180672, E-Mail:

Yicheng Xie and Fan Liu are postgraduates at Jiangnan University and are involved in synthesis and analysis of surfactants.

Jiajia Liu is a bachelor at Jiangnan University and are involved in synthesis and analysis of surfactants.

Hujun Xu is an associate professor at Jiangnan University, P.R. China. He received his Ph.D. degree in 2005 from Nanjing University of Science and Technology, P.R. China. He has been involved in surfactants and detergents for over 30 years. He has published over 60 papers in the field of surfactants and detergents.


References

1. Song, L. D. and Rosen, M. J.: Langmuir.12 (1996) 11491153. 10.1021/la950508tSearch in Google Scholar

2. Menger, F. M. and Littau, C. A.: J. Am. Chem. Soc.115 (1993) 1008310090. 10.1021/ja00075a025Search in Google Scholar

3. Menger, F. M. and Littau, C. A.: J. Am. Chem. Soc.113 (1991) 14511452. 10.1021/ja00004a077Search in Google Scholar

4. Kunieda, H., Kaneko, M., Feng, J. and Tsubone, K.: J. Oleo Sci.51 (2002) 761769. 10.5650/jos.51.761Search in Google Scholar

5. Xu, H., Liu, B., Kang, P. and Bao, X.: J. Surfactants Deterg.18 (2015) 297302. 10.1007/s11743-014-1655-5Search in Google Scholar

6. Shukla, D. and Tyagi, V. K.: J.: Oleo Sci.55 (2006) 381390. 10.5650/jos.55.381Search in Google Scholar

7. Zana, R.: Advances in Colloid and Interface Science.97 (2002) 205253. 10.1016/S0001-8686(01)00069-0Search in Google Scholar

8. Menger, F. M. and Keiper, J. S.: Angewandte Chemie.39 (2000) 19061920. 10.1002/1521-3773(20000602)39:11<1906::AID-ANIE1906>3.0.CO;2-Search in Google Scholar

9. Song, C. P., Wu, D. Q., Zhang, F. and Liu, P.: Chemical Communications.48 (2012) 21192121. 10.1039/c2cc16890aSearch in Google Scholar

10. Zana, R.: Journal of Colloid and interface Science.252 (2002) 259261. PMid:16290787; 10.1006/jcis.2002.8457Search in Google Scholar

11. Jaeger, D. A.: Langmuir.12 (1996) 19761980. 10.1021/la950872sSearch in Google Scholar

12. Shi, L. W. and Xue, Y.: Petroleum asphalt.21 (2007) 122126. 10.3969/j.issn.1672-3961.2007.03.024Search in Google Scholar

13. Ding, Y. S., Zha, M. and Zhang, J.: Colloids and Surfaces A: Physicochemical and Engineering Aspects.298 (2007) 201205. 10.1016/j.colsurfa.2oo6.10.063Search in Google Scholar

14. Pierluigi, Q., Guido, V. and Claudia, B.: Journal of Organic Chemistry.68 (2003) 765160. PMid:14510538; 10.1021/jo034602nSearch in Google Scholar PubMed

15. Avinash, B. and Sukhprit, S.: Langmuir.25 (2009) 1170312. PMid:19788223; 10.1021/la901641fSearch in Google Scholar PubMed

16. Qiu, L. G., Xie, A. J. and Shen, Y. H.: Journal of Physical Oceanography.91 (2005) 269273. 10.1016/j.matchemphys.2004.11.022Search in Google Scholar

17. Caillier, L., Givenchy, E. T. D. and Levy, R.: Journal of Colloid & Interface Science.332 (2009) 2017. PMid:19144354; 101016/j.jcis.2008.12.038Search in Google Scholar

18. Bhadani, A. and Singh, S.: Langmuir.27 (2011) 1403344. PMid:22004288; 10.1021/la202201rSearch in Google Scholar PubMed

19. Saif, M. J., Anwar, J. and Munawar, M. A.: Arkivoc Online Journal of Organic Chemistry.43 (2010) 133145. 10.1016/S0021-9797(03)00694-5Search in Google Scholar PubMed

20. Menger, F. M., Keiper, J. S. and Azov, V.: Langmuir.16 (1999) 20622067. 10.1021/la9910576Search in Google Scholar

21. Wahhab, A. A. and Asi, I. M.: Building and Environment.32 (1997) 271279. 10.1016/S0360-1323(96)00067-4Search in Google Scholar

22. Niazi, Y. and Jalili, M.: Construction and Building Materials.23 (2009) 13381343. 10.1016/j.conbuildmat.2008.07.020Search in Google Scholar

23. Huai, C., Shi, L. and Li, N.: Research on Chemical Intermediates.39 (2013) 597614. 10.1007/s11164-012-0582-1Search in Google Scholar

24. Li, H. P., Zhao, H. and Liao, K.: Energy Sources Part A Recovery Utilization and Environmental Effects.35 (2013) 22852293. 10.1080/15567036.2011.551927Search in Google Scholar

25. Li, Z. X. and And, C. C. D.: Langmuir.15 (1999) 43924396. 10.1021/la981551uSearch in Google Scholar

26. Nudelman, A.: Journal of Organic Chemistry.21 (1997) 75127515. 10.1021/jo971176vSearch in Google Scholar PubMed

27. Xu, H., Chen, D. and Cui, Z.: J. Surfactants Deterg.14 (2011) 167172. PMid:21841907; 10.1007/s11743-010-1213-8Search in Google Scholar

Received: 2016-09-13
Accepted: 2017-05-24
Published Online: 2017-09-06
Published in Print: 2017-09-15

© 2017, Carl Hanser Publisher, Munich

Downloaded on 26.11.2025 from https://www.degruyterbrill.com/document/doi/10.3139/113.110521/pdf?lang=en
Scroll to top button