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An Advanced Method for the Preparation of Erucyl Dimethyl Amidopropyl Betaine and Acid Solution Properties

Eine erweiterte Methode zur Herstellung von Erucyldimethylamidopropylbetain und die Eigenschaften saurer Lösungen
Hongsheng Lu, Xuan Zhang, Hongping Quan, Shanshan Dai, Tailiang Zhang and Zhiyu Huang

Abstract

In this paper, an improved method for the preparation of erucyl dimethyl amidopropyl betaine (EDAB) was provided. The synthesis conditions were investigated. N,N-dimethyl-N′-erucyl-1,3-propylenediamine was synthesized by the reaction of erucic acid with N,N-dimethyl-1,3-propylenediamine at 170°C for 7 h, and then the intermediate was reacted with sodium chloroacetate in the mixture of methanol and water (3:7 v/v) at 60°C. The product was obtained after 6 h. The compounds were confirmed by IR and 1H-NMR. The properties of EDAB acid solution were also studied. The results indicated that viscosity of acid solution increased with decreasing hydrochloric acid concentration and was mainly controlled by surfactant concentration and temperature. The viscosity of an acid solution was maximum when the concentration of hydrochloric acid was at 15 wt%.

Kurzfassung

In diesem Manuskript wird eine verbesserte Methode zur Herstellung von Erucyldimethylamidopropylbetain (EDAB) vorgestellt. Die Synthesebedingungen wurden untersucht. N,N-Dimethyl-N′-erucyl-1,3-propylenediamin wurde erzeugt, in dem man Erucasäure mit N,N-Dimethyl-1,3-propylenediamin 7 Stunden bei 170°C reagieren ließ. Das Zwischenprodukt wurde dann bei 60°C mit Natriumchloracetat in einer Lösemittelmischung aus Methanol und Wasser (3:7, v/v) umgesetzt. Nach 6 Stunden erhielt man das Endprodukt. Die Verbindungen wurden mittels IR und 1H-NMR bestätigt. Die Eigenschaften der sauren EDAB-Lösung wurden auch untersucht. Die Ergebnisse zeigten, dass die Viskosität der sauren Lösung mit abnehmender Salzsäurekonzentration zunahm. Sie wurde hauptsächlich von der Tensidkonzentration und der Temperatur kontrolliert. Bei einer Salzsäurekonzentration von 15 w% trat ein Viskositätsmaximium der sauren Lösung auf.


Mr. Xuan Zhang, School of Chemistry and Chemical Engineering, Southwest Petroleum University, Xindu, Sichuan 610500, P.R. China, E-Mail:

Dr Hongsheng Lu is currently a teacher at the College of Chemistry and Chemical Engineering, Southwest Petroleum University. He received his Ph.D. in Chengdu Institute of Organic Chemistry of Chinese Academy of Sciences. His research interests include synthesis and application of oil chemicals.

Mr. Xuan Zhang is currently a M.D. candidate at the College of Chemistry and Chemical Engineering, Southwest Petroleum University. His main research is synthesis of viscoelastic surfactant using in acidizing stimulation.

Dr. Hongping Quan is currently a teacher at the College of Chemistry and Chemical Engineering, Southwest Petroleum University. He received his Ph.D. in Applied Chemistry at the College of Chemistry and Chemical Engineering, Southwest Petroleum University. His research interests include synthesis and application of oil chemicals.

Dr. Shanshan Dai is currently a teacher at the College of Chemistry and Chemical Engineering, Southwest Petroleum University. She received her Ph.D. in the College Polymer Science and Engineering in Sichuan University. Her research interests include synthesis and application of oil chemicals.

Dr. Tailiang Zhang is currently a teacher at the College of Chemistry and Chemical Engineering, Southwest Petroleum University. He received his Ph.D. in Applied Chemistry at the College of Chemistry and Chemical Engineering, Southwest Petroleum University. His research interests include synthesis and application of oil chemicals.

Prof. Zhiyu Huang is currently the director of Graduate School, Southwest Petroleum University. He received his Ph.D. in Applied Chemistry at the College of Chemistry and Chemical Engineering, Southwest Petroleum University. His research interests include synthesis and application of oil chemicals.


References

1. Hoffmann, H.: Structure and Flow in: Surfactant Solutions, Herb, C. A., Prud'homme, R. K., Eds., American Chemical Society: Washington, DC (1994) 2.10.1021/bk-1994-0578.ch001 Search in Google Scholar

2. Cates, M. E.: Macromolecules20 (1987) 2289.10.1021/ma00175a038 Search in Google Scholar

3. Danino, D., Talmon, Y., Levy, H., Beinert, G. and Zana, R.: Science269 (1995) 1420.10.1126/science.269.5229.1420 Search in Google Scholar

4. Zana, R. and Kaler, E. W., (Eds.) Giant Micelles: Properties and Applications, Surfactant Series, CRC Press: Boca Raton, FL140 (2007). Search in Google Scholar

5. Cates, M. E.: Macromolecules20 (1987) 2289.10.1021/ma00175a038 Search in Google Scholar

6. Siriwatwechakul, W., LaFleur, T., Prud'homme, R. K. and Sullivan, P.: Langmuir20 (2004) 8970.10.1021/la035853u Search in Google Scholar

7. Raghavan, S. R., Fritz, G. and Kaler, E. W.: Langmuir18 (2002) 3793. Search in Google Scholar

8. Croce, V., Cosgrove, T., Dreiss, C. A., Maitland, G., Hughes, T. and Karlsson, G.: Langmuir20 (2004) 7984.10.1021/la0487500 Search in Google Scholar

9. Siriwatwechakul, W., LaFleur, T., Prud'homme, R. K. and Sullivan, P.: Langmuir20 (2004) 8970.10.1021/la035853u Search in Google Scholar

10. Bakshi, M. S., Kaur, G., Yoshimura, T. and Esumi, K.: Colloids and Surfaces A: Physicochem. Eng. Aspects281 (2006) 163170.10.1016/j.colsurfa.2006.02.058 Search in Google Scholar

11. Bakshi, M. S., Singh, J., Singha, K. and Kaur, G.: Journal of Photochemistry and Photobiology A: Chemistry169 (2005) 6370.10.1016/j.jphotochem.2004.04.017 Search in Google Scholar

12. Bakshi, M. S., Singh, K. and Singh, J.: Journal of Colloid and Interface Science297 (2006) 284291.10.1016/j.jcis.2005.10.034 Search in Google Scholar

13. Bakshi, M. S., Singh, J. and Kaur, G.: Chemistry and Physics of Lipids138 (2005) 8192.10.1016/j.chemphyslip.2005.08.005 Search in Google Scholar

14. Yang, J.: Curr. Opin. Colloid Interface Sci.7 (2002) 276.10.1016/S1359-0294(02)00071-7 Search in Google Scholar

15. Zakin, J. L. and Bewersdroff, H. W.: Rev. Chem. Eng.14 (1998) 253.10.1515/REVCE.1998.14.4-5.253 Search in Google Scholar

16. Qi, Y. and Zakin, J. L.: Ind. Chem. Res.41 (2002) 6326.10.1021/ie0110484 Search in Google Scholar

17. Soussan, E., Cassel, S., Blanzat, M. and Rico-Lattes, I.: Angew. Chem., Int. Ed.48 (2009) 274.10.1002/anie.200802453 Search in Google Scholar

18. Dwars, T., Paetzold, E. and Oehme, G.: Angew. Chem. Int. Ed.44 (2005) 7174.10.1002/anie.200501365 Search in Google Scholar

19. Zemb, Th., Budois, M., Deme, B. and Gulik-Krzywicki, Th.: Science283 (1999) 816.10.1126/science.283.5403.816 Search in Google Scholar

20. Lin, H. and Mou, Ch.: Acc. Chem. Res.35 (2002) 927.10.1021/ar000074f Search in Google Scholar

21. Stukan, M. R., Boek, E. S., Padding, J. T., Briels, W. J. and Crawshaw, J. P.: Soft Matter4 (2008) 870.10.1039/b713498c Search in Google Scholar

22. Ezrahi, S., Tuval, E. and Aserin, A.: Adv. Colloid Interface Sci.77 (2006) 128. Search in Google Scholar

23. Chase, B., Wells, N., Territories, N., Chmilowski, W., Marcinew, R., Mitchell, C., Dang, Y., Krauss, D., Nelson, E., Lantz, T., Parham, C. and Plummer, J.: Oilfield Rev.9 (1997) 20. Search in Google Scholar

24. Samuel, M., Card, R. and Nelson, E.: SPE Annual Technical Conference and Exhibition: San Antonio, Texas SPE38622 (1997). Search in Google Scholar

25. Miller, M. and Dismuck, K.: Ross. Khim. Zh.47 (2003) 78. Search in Google Scholar

26. Alleman, D., Qu, Q. and Keck, R.: SPE International Symposium on Oilfield Chemistry: Lafayette, Louisiana SPE80222 (2003). Search in Google Scholar

27. Chang, F., Qu, Q. and Frenier, W.: SPE International Symposium on Oilfield Chemistry: Houston, Texas SPE65033 (2001). Search in Google Scholar

28. Huang, T. and Crews, J.: SPE International Symposium on Oilfield Chemistry: Houston, Texas SPE112484 (2008). Search in Google Scholar

29. Zheng, Y., Zhao, L., Liu, P. and Shen, J.: Drilling Fluid & Completion Fluid (2006) 23. Search in Google Scholar

30. Volkbert, B. and Essen, F.: US Patent No.,: 4 832 871 (1989). Search in Google Scholar

31. Volkbert, B. and Essen, F.: US Patent No.,: 4 861 517 (1989). Search in Google Scholar

32. QB/T 2344–1997. Search in Google Scholar

33. EN 15608: 2008. Search in Google Scholar

Received: 2012-02-01
Revised: 2012-05-19
Published Online: 2013-04-05
Published in Print: 2012-11-01

© 2012, Carl Hanser Publisher, Munich