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Synthesis and Properties of Monododecyl Diphenyl Methane Disulfonate

  • Feng-Mei Xing , Xiao-Chen Liu , Jin-Ping Niu and Xiao-Yu Wang
Published/Copyright: August 16, 2013
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Abstract

A gemini surfactant with asymmetric molecular structure, monododecyl diphenyl methane disulfonate surfactant (MDDMDS), was synthesized by Friedel-Crafts reaction of dodecanol with diphenyl methane in the presence of active bleach clay, followed by sulfonation with liquid sulfur trioxide. The surface activity, salinity and hardness tolerance, wettability alteration and spontaneous emulsification of this asymmetric gemini surfactant were investigated. The critical micelle concentration (CMC) was 9.1 × 10−5 mol · L−1, the surface tension (γcmc) was 38.4 mN · m−1. Sodium chloride tolerance and calcium chloride tolerance reached 20.55 wt.% and 17.01 wt.%, respectively. This surfactant altered the wettability of the PTFE-film surface from oil-wet to less oil-wet or intermediate wet and show preferable property of emulsifying the crude oil.

Kurzfassung

Mit Hilfe der Friedel-Crafts-Reaktion von Dodecanol mit Diphenylmethan in Gegenwart von aktivem Bleichton, auf die eine Sulfonierung mit flüssigem Schwefeltrioxid folgte, wurde ein Gemini-Tensid (Monodedecyldiphenylmethandisulfonat, MDDMDS) mit einer asymmetrischen Molekülstruktur synthetisiert. Es wurden die Oberflächenaktivität, die Härtetoleranz, das Benetzungsvermögen und die spontane Emulsionsbildung des asymmetrischen Tensids untersucht. Die kritische Mizellbildungskonzentration (CMC) betrug 9.1 × 10−5 mol · L−1, die Oberflächenspannung bei der CMC (γcmc) 38.4 mN · m−1. Die Natriumchloridtoleranz hatte einen Wert von 20,55 wt.%, die Calciumtoleranz einen von 17,01 wt.%. Das Tensid veränderte die Benetzung auf einem PTFE-Film von gut öl-benetzend zu wenig öl-benetzend bzw. mittel wasser-benetzend. Das Tensid besitzt eine wünschenswerte Emulgiereigenschaft mit Rohöl.


* Correspondence address, Mrs. Feng-Mei Xing, Mrs. Jin-Ping Niu, China Research Institute of Daily Chemical Industry, 34 Wenyuan Street, Taiyuan 030001, Shanxi Province, P. R. China, Tel: 00 86-3 51-4 19 28 78, Fax: 00 86-3 51-4 04 08 02, E-Mail: ,

Fengmei Xing was born in 1 985. Presently she is working for Master degree at China Research Institute of Daily Chemical Industry. Her main field of research is synthesis and properties on surfactant of diaryl sulfonate.

Jinping Niu was born in 1 966. Her research interests are sulfonation or sulfation of organic materials.

Xiaochen Liu is engineer of China Research Institute of Daily Chemical Industry. His research interest is synthesis and investigation of novel sulfonate.

Xiaoyu Wang is engineer of China Research Institute of Daily Chemical Industry. Her research interest is synthesis and application of surfactants.


References

1. Tsubone, K. and Ghosh, S.: Micellization of an Anionic Gemini Surfactant Having N,N-Dialkylamide, Carboxyl, and Carboxylate Groups in Aqueous NaCl Solutions. J. Surfact. Deterg.7 (1) (2004) 4752. 10.1007/s11743-004-0287-9Search in Google Scholar

2. Chen, H., Han, L. J., Luo, P. Y. and Ye, Z. B.: The Interfacial Tension Between Oil and Gemini Surfactant Solution, Surface Sci.552 (1–3) (2004) L53L57. 10.1016/j.susc.2004.01.018Search in Google Scholar

3. Caracciolo, G., Mancini, G., Bombelli, C. and Caminiti, R.: Structural Features of a Cationic Gemini Surfactant at Full Hydration Investigated by Energy Dispersive X-ray Diffraction. Chem. Phys. Lett.386 (1–3) (2004) 7682. 10.1016/j.cplett.2004.01.038Search in Google Scholar

4. Krishnan, R. S. G., Thennarasu, S. and Mandal, A. B.: Self-Assembling Characteristics of a New Nonionic Gemini Surfactant. J. Phys. Chem. B.108 (26) (2004) 88068816. 10.1021/jp037554jSearch in Google Scholar

5. Xu, J., Han, S. H., Hou, W. G., Dang, W. X. and Yan, X.: Synthesis of High-Quality MCM-48 Mesoporous Silica Using Cationic Gemini Surfactant C12-2-12. Colloids Surf. A.248 (1–3) (2004) 7578. 10.1016/j.colsurfa.2004.08.069Search in Google Scholar

6. Zhou, T. H., Yi, Y. and Zhao, J. X.: Synthesis of Heterogemini Surfactants. Fine Chem Icals.24 (1) (2007) 3438.Search in Google Scholar

7. International Organization for Standardization, Animal and Vegetable Fats and Oils-Determination of Iodine Value, ISO, Geneva, Switzerland, ISO Standard (1989) 3961.Search in Google Scholar

8. Coleman, G. H., Perkins, R. P. and Mich, M.: Alkylated Diphenyloxide. U.S. Patent 2170809 (1939).Search in Google Scholar

9. Steinhauer, A. F. and Midland, M.: Method of making alkyl diphenyl ether sulfonates. U.S. Patent2854477 (1958).Search in Google Scholar

10. Du, X. G., Lu, Y., Li, L., Wang, J. B. and Yang, Z. Y.: Synthesis and unusual properties of novel alkylbenzene sulfonate Gemini surfactants. Colloids and Surfaces A: Physicochem. Eng. Aspects290 (1–3) (2006) 132137. 10.1016/j.colsurfa.2006.05.013Search in Google Scholar

11. Wang, B. L., Wang, H., Wang, E., Yan, W. J., Ye, W. C. and Li, P.: Isolation and structure characterization of related impurities in Sodium Tanshinone-A Sulfonate by LC/ESI-MSn and NMR. Journal of Pharmaceutical and Biomedical Analysis. 67–68 (2012) 3641. 10.1016/j.jpba.2012.04.029Search in Google Scholar PubMed

12. Zhang, D. L., Wang, C. H. and WangG.Y.: Synthesis and Properties of a New Tetrasiloxane-tailed Dicephalic Surfactant. Tenside Surf. Det.49 (2) (2012) 151155.Search in Google Scholar

13. Liu, Q., Dong, M. Z., Yue, X. G. and Hou, J. R.: Synergy of alkali and surfactant in emulsication of heavy oil in brine. Colloids and Surfaces A: Physcochem. Eng. Aspects273 (1–3) (2006) 219228. 10.1016/j.colsurfa.2005.10.016Search in Google Scholar

14. Zhao, S. J., Cheng, F., Chen, Y., Wei, Y. P. and Yu, Z. L.: Synthesis and Properties of Gemini Surfactants, Journal of Tianjin University.45 (1) (2012) 8186.Search in Google Scholar

15. Zana, R., Benrraou, M. and Rueff, R.: Alkanediyl-α,ω-bis(dimethylalky1ammonium bromide) Surfactant. 1. Effect of the Spacer Chain Length on the Critical Micelle Concentration and Micelle Ionization Degree. Langmuir7 (1991) 10721075. 10.1021/la00054a008Search in Google Scholar

16. Dahanayake, M., Cohen, A. W. and Rosen, M. J.: J. Phys. Chem.90 (1986) 24132418. 10.1021/j100402a032Search in Google Scholar

17. Li, X., Hu, Z. Y., Zhu, H. L., Zhao, S. F. and Cao, D. L.: Synthesis and properties of novel alkyl sulfonate Gemini surfactants, J. Surfact. Deterg.13 (2010) 353359. 10.1007/s11743-010-1188-5Search in Google Scholar

18. Zhao, G. X. and Zhu, B. Y.: Principles of Surfactant Action, Light Industry Press. Beijing (2003) 700–704.Search in Google Scholar

19. Tatsumi, T., Zhang, W., Kida, T., Nakatsuji, Y., Ono, D. and Takeda, T.: Ikeda I (2000) Novel hydrolysable and biodegradable cationic Gemini surfactants: 1,3-Bis[(acyloxyalkyl)-dimethylammonio]-2-hydroxypropanedichloride. J. Surfact. Deterg.2, 167172.10.1007/s11743-000-0121-4Search in Google Scholar

20. Piasecki, A., Wójcik, B., Luczyński, J., Pilakowska-Pietras, D., Witek, S. and Krasowska, A.: Bifunctional N-oxides of Alkyldiamidoamines. J. Surfact. Deterg.12 (2009) 201207. 10.1007/s11743-009-1111-0Search in Google Scholar

21. Rosen, M. J.: Surfactants and Interfacial Phenomena, Seconded, Wiley, New York, 1989.Search in Google Scholar

22. Tusbone, K. and Rosen, M. J.: Structural effect on surface activities of anionic surfactants having N-acyl-N-methylamide and carboxylate groups. J. Colloid and Interface Sci.244 (2) (2001) 394398. 10.1006/jcis.2001.7995Search in Google Scholar

23. Stellner, K. L. and Scamehorn, J. F.: Hardness tolerance of anionic surfactant solutions. 1. Anionic surfactant with added monovalent electrolyte. Langmuir5 (1) (1989) 7077.Search in Google Scholar

24. Scamehorn, J. F. and Harwell, J. H.: Precipitation of Surfactant Mixtures 2005.10.1201/9781420031010.ch18Search in Google Scholar

25. Wagner, R., Wu, Y., Berlepsch, H. V., Rexin, F., Rexin, T. and Perepelittchenko, L.: Appl. Organomet. Chem.13 (9) (1999) 621630. 10.1002/(SICI)1099-0739(199909)13:9<621::AID-AOC885>3.0.CO;2-ASearch in Google Scholar

26. Ayirala, S. C., Vijapurapu, C. S. and Rao, D. N.: Beneficial effects of wettability altering surfactants in oil-wet fractured reservoirs, Journal of Petroleum Science and Engineering52 (2006) 261274. 10.1016/j.petrol.2006.03.019Search in Google Scholar

27. Salehi, M., Johnson, S. J. and Liang, J. T.: Enhanced wettability alteration by surfactants with muitiple hydrophilic moieties. J. Surfact. Deterg.13 (2010) 243246. 10.1007/s11743-010-1193-8Search in Google Scholar

Received: 2012-10-8
Published Online: 2013-08-16
Published in Print: 2013-05-15

© 2013, Carl Hanser Verlag, Munchen

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