Synthesis of Dodecyl Lauroyl Benzene Sulfonate and its Application in Enhanced Oil Recovery

Z. Cui; L. Wu; M. Sun; J. Jiang; F. Wang

doi:10.3139/113.110147

Published by De Gruyter April 11, 2013

Synthesis of Dodecyl Lauroyl Benzene Sulfonate and its Application in Enhanced Oil Recovery

Synthese von Dodecyllaurylbenzensulfonat und seine Anwendung in der tertiären Erdölförderung

Z. Cui , L. Wu , M. Sun , J. Jiang and F. Wang

From the journal Tenside Surfactants Detergents

https://doi.org/10.3139/113.110147

Showing a limited preview of this publication:

Abstract

A new hydrophobic surfactant, dodecyl lauroyl benzene sulfonate (DLBS), was synthesized and its application in enhanced oil recovery by alkali-surfactant-polymer (ASP) flooding was studied. The results show that DLBS can be synthesized by reaction of industrial dodecyl benzene with lauroyl chloride in the presence of AlCl₃, followed by sulfonation with ClSO₃H and neutralization with NaOH. The lauroyl-group is confirmed to be connected to the para-position of the alkylbenzene by ¹HNMR spectrum. The synthesized DLBS is well soluble in pure water and reservoir (connate) water at 45°C. It is highly surface active which is indicated by its low CMC of 1.1 · 10⁻⁵ mol/L, and its low surface tension, γ_cmc of 28.6 mN m⁻¹. By mixing with heavy alkylbenzene sulfonates of relatively low average molar mass (387 g mol⁻¹) at a total surfactant concentration of 5 mM, DLBS can reduce the interfacial tension of Daqing crude oil/connate water to an order of 10⁻³ mN/m at 45°C in the presence of 0.5–1.0 wt.% NaOH and 1000 mg L⁻¹ of polymer. If the NaOH was replaced by a gentle alkaline salt, Na₂CO₃, certain amounts of dodecyl dimethyl carboxy betaine were added and the concentration of Na₂CO₃ was increased to 1.2–2.0 wt.%, the interfacial tension of Daqing crude oil/connate water can also be reduced to an ultralow value. Therefore DLBS is a good hydrophobic surfactant applicable in ASP flooding with either NaOH or Na₂CO₃ as alkaline agents.

Kurzfassung

Ein neues hydrophobes Tensid, Dodecyllaurylbenzensulfonat (DLBS), wurde synthetisiert und sein Einsatz beim Alkali-Tensid-Polymer-Fluten (ASP-Fluten) in der tertiären Erdölförderung untersucht. Die Ergebnisse zeigen, dass DLBS hergestellt werden kann, in dem industrielles Dodecylbenzen mit Laurylchlorid in Anwesenheit von AlCl₃ reagiert. Das Reaktionsprodukt wird nachfolgend mit ClSO₃H sulfoniert. Anschließend erfolgt eine Neutralisation mit NaOH. Die Laurylgruppe ist in para-Stellung an das Alkylbenzen gebunden, was durch ein ¹HNMR-Spektrum bestätigt ist. Das synthetisierte DLBS ist in reinem Wasser gut löslich und bei 45°C ebenfalls gut löslich in konnaten Wässern. Es ist hoch oberflächenaktiv, was aufgrund seiner niedrigen CMC von 1.1 · 10⁻⁵ mol/L und der Oberflächenspannung bei der CMC, γ_cmc, von 28.6 mN m⁻¹ deutlich wird. In einer Mischung aus schweren linearen Alkylbenzensulfonaten mit geringer mittlerer Molmasse (387 g mol⁻¹), 0.5–1.0 wt.% NaOH und 1000 mg L⁻¹ Polymer, wobei die Gesamttensidkonzentration 5 mM betrug, konnte DLBS die Grenzflächenspannung von Mischungen aus Daqing-Rohöl und konnaten Wässern auf eine Größenordnung von 10⁻³ mN/m bei 45°C herabsetzen. Wenn NaOH durch ein weniger alkalisches Salz (Na₂CO₃) ersetzt wurde, wobei der Na₂CO₃-Anteil auf 1.2–2.0 wt.% erhöht wurde, und der Mischung noch zusätzlich definierte Mengen an Dodecyldimethylcarboxybetaine zugegeben wurden, konnte ebenfalls die Grenzflächenspannung von Daqing-Rohöl und konnatem Wasser auf ultraniedrige Werte reduziert werden. Daher ist DLBS ein gutes hydrophobes Tensid, das beim alkalischen ASP-Fluten sowohl mit NaOH als auch mit Na₂CO₃ eingesetzt werden kann.

Key words:: Dodecyllauroylbenzene sulfonate; heavy alkylbenzene sulfonate; ultralow interfacial tension; ASP flooding; Enhanced oil recovery

Stichwörter:: Dodecyllaurylbenzensulfonat; schwere Alkylbenzensulfonate; ultraniedrige Grenzflächenspannung; ASP-Flutung; tertiäre Erdölförderung

^∗ Dr. Zhenggang Cui, School of Chemical and Material Engineering, Jiangnan University, 1800 Lihu Road, 214122 Wuxi, Jiangsu, P.R. China, Tel.: 86-13382888025, Fax: 86-510-85917763. E-Mail: cuizhenggang@hotmail.com

Zheng-gang Cui received a B.Sc. and M.Sc. in Fine Chemical Engineering from Wuxi Institute of Light Industry, P.R. China, in 1982 and 1987, and received a Ph.D. in Physical Chemistry in 2006 from Hull University, UK. He is currently a professor in School of Chemical and Material Engineering, Jiangnan University, P.R. China. His research interests include surfactants and colloids, especially new surfactants for EOR.

Le Wu is currently a M.Sc. student in School of Chemical and Material Engineering, Jiangnan University, P.R. China. He is involved in synthesis and applications of new surfactants for EOR.

Mingming Sun is just graduated from School of Chemical and Material Engineering, Jiangnan University, P.R. China. He was involved in synthesis and applications of new surfactants for EOR as an undergraduate student.

Jian-zhong Jiang received a Ph.D. in Applied Chemistry from Nanjing University of Science and Technology, P.R. China, in 2007 and is currently an associate professor in School of Chemical and Material Engineering, Jiangnan University, P.R. China. His research interests include organic synthesis, microemulsion, and applications of surfactants in organic synthesis.

Feng Wang received a Ph.D. in Bioengineering from Jiangnan University, P.R. China in 2005 and is currently an associate professor in School of Chemical and Material Engineering, Jiangnan University, P.R. China. His research interests include organic synthesis, surfactants for EOR and biochemicals.

References

1. Egbogah, E. O.: Journal of Petroleum Science and Engineering.10 (1994) 337. 10.1016/0920-4105(94)90024-8Search in Google Scholar

2. BabadagliT.: Journal of Petroleum Science and Engineering.57 (2007) 221. 10.1016/j.petrol.2006.10.006Search in Google Scholar

3. Zhang, J. C.: Tertiary Oil Recovery. Beijing: China Petroleum Industry Press. (1995). (Ch.)Search in Google Scholar

4. Nedjhioui, M., Moulai-Mostefa, N., Morsli, A. and Bensmaili, A.: Desalination185 (2005) 543. 10.1016/j.desal.2005.05.013Search in Google Scholar

5. Carrero, E., Queipo, N. V., Pintos, S. and Zerpa, L. E.: Journal of Petroleum Science and Engineering58 (2007) 30. 10.1016/j.petrol.2006.11.007Search in Google Scholar

6. Dong, M. Z., Ma, S. Z. and Liu, Q.: Fuel88 (2009) 1049. 10.1016/j.fuel.2008.11.014Search in Google Scholar

7. Taylor, K. C., Nasr-El-Din, H. A.: Colloid and Surfaces A.108 (1996) 49. 10.1016/0927-7757(95)03364-5Search in Google Scholar

8. Chatterjee, J., Wasan, D. T.: Chemical Engineering Science53 (1998) 2711. 10.1016/S0009-2509(98)00093-1Search in Google Scholar

9. Chatterjee, J., Wasan, D. T.: Colloid and Surfaces A132 (1998) 107. 10.1016/S0927-7757(97)00195-7Search in Google Scholar

10. Cao, Y., Li, H.: European Polymer Journal38 (2002) 1457. 10.1016/S0014-3057(02)00016-2Search in Google Scholar

11. Liu, Q., Dong, M., Zhou, W., Ayub, M., Zhang, Y. P. and Huang, S.: Journal of petroleum science and technology43 (2004) 75.Search in Google Scholar

12. Nedjhioui, M., Moulai-Mostefa, N., Morsli, A. and Bensmaili, A.: Desalination185 (2005) 543. 10.1016/j.desal.2005.05.013Search in Google Scholar

13. Yang, J., Qiao, W., Li, Z. and Cheng, L.: Fuel84 (2005) 160.Search in Google Scholar

14. Zhang, S., Yan, J., Qi, H., Luan, J., Qiao, W. and Li, Z.: Journal of Petroleum Science and Engineering47 (2005) 117. 10.1016/j.petrol.2005.03.004Search in Google Scholar

15. Zhang, H., Dong, M. and Zhao, S.: Energy Fuels24 (2010) 1829. 10.1021/ef901310vSearch in Google Scholar

16. Kang, W. L., Shan, X. L.: P.G.O.D.D.17 (1998) 32. (Ch.)Search in Google Scholar

17. Shan, X. L., Kang, W. L., Sun, H. Y., Li, D. S. and Li, J. G.: Journal of Daqing Petroleum Institute23 (1999) 32. (Ch.)Search in Google Scholar

18. Liao, G. Z., Yang, Z. Y. and Liu, Y.: P.G.O.D.D.20 (2001) 40. (Ch.)Search in Google Scholar

19. Jiao, Y. H., Xu, Z. G., Qiao, W. H., Li, Z. S. and Cheng, L. B.: Journal of Dalian University of Technology44 (2004) 44. (Ch.)Search in Google Scholar

20. Guo, W. K., Yang, Z. Y., Wu, X. L., Zhang, G. Y. and Wang, H. F.: Acta Petrol EI Sinica27 (2006) 75. (Ch.)Search in Google Scholar

21. Yue, X. Y., Lou, Z. H., Han, D. and Yuan, S. Y.: Advances in Fine Petrochemicals.5 (2004) 7. (Ch.)Search in Google Scholar

22. Hou, J. R., Li, Z. Q. and Yue, X. A.: P.G.O.D.D.25 (2006) 82. (Ch.)Search in Google Scholar

23. Cui, Z. G., Zou, W. H., Zhang, T. L. and Zhang, D. G.: Journal of East China University of Science and Technology (Natural Science Edition)25 (1999) 339. (Ch.)Search in Google Scholar

24. Li, G. Z., Lin, Y. and Xu, G. Y.: Journal of Oilfield Chemistry11 (1994) 61. (Ch.)Search in Google Scholar

25. Huang, H. D.: Journal of Oilfield Chemistry8 (1991) 235. (Ch.)Search in Google Scholar

26. Han, M., Kang, X. D., Zhang, J. and Xiang, W. T.: China Offshore Oil and Gas.18 (2006) 408. (Ch.)Search in Google Scholar

27. Zhao, F. L.: Journal of China University of Petroleum (Natural Science Edition)31 (2007) 163. (Ch.)Search in Google Scholar

28. Aoudia, M., Al-Shibli, MN., Al-Kasimi, LH., Al-Maamari, R. and Al-Bemani, A.: Journal of Surfactants and Detergents9 (2006) 287. 10.1007/s11743-006-5009-9Search in Google Scholar

29. Zhao, Z. K., Bi, C. G., Qiao, W. H., Li, Z. S. and Cheng, L.: Colloids and Surfaces A.294 (2007) 191. 10.1016/j.colsurfa.2006.08.011Search in Google Scholar

30. Wu, Y., Iglauer, S., Shuler, P. J., Tang, Y. and Goddard, W. A.: Tenside Surfactants Detergents47 (2010) 280.Search in Google Scholar

31. Wu, Y., Iglauer, S., Shuler, P. J., Tang, Y. and Goddard, W. A.: Tenside Surfactants Detergents.47 (2010) 152.Search in Google Scholar

32. Iglauer, S., Wu, Y., Shuler, P. J., Tang, Y. and Goddard, W. A.: Journal of Petroleum Science and Engineering71 (2010) 23. 10.1016/j.petrol.2009.12.009Search in Google Scholar

33. Iglauer, S., Wu, Y., Shuler, P. J., Tang, Y. and Goddard, W. A.: Tenside Surfactants Detergents47 (2010) 87.Search in Google Scholar

34. Iglauer, S., Wu, Y., Shuler, P. J., Tang, Y. and Goddard, W. A.: Colloids and Surfaces A.339 (2009) 48. 10.1016/j.colsurfa.2009.01.015Search in Google Scholar

35. Xiao, Y. Y. and Zhang, P. F.: China Surfactant, Detergent, and Cosmetics4 (1986) 44. (Ch.)Search in Google Scholar

36. Gong, Q. T., Wang, L., Wang, D. X., Yang, Z. Y., Zhao, J. S., Wang, Y. Y., Zhang, L., An, J. Y., Zhao, S. and Yu, J. Y.: Fine Chemicals.22 (2005) 189. (Ch.)Search in Google Scholar

37. Gong, Q. T., Jiang, X. M., Wang, L., Zhao, J. S., Wang, D. X., Zhang, l., Zhao, S. and Yu, J. Y.: Journal of Petrochemical Universities.18 (2005) 20. (Ch.)Search in Google Scholar

38. Wang, L., Gong, Q. T., Wang, D. Y., Zhao, S., An, J. Y. and Yu, J. Y.: Petrochemical Technology.33 (2004) 104. (Ch.)Search in Google Scholar

39. Zhang, L. M., Zhang, Q. and Chen, H.: Chemical Engineering of Oil and Gas36 (2007) 416. (Ch.)Search in Google Scholar

40. Wang, R.: Dissertation for the Master degree in Science of Daqing Petroleum Institute. 2007. (Ch.)Search in Google Scholar

41. Longman, G. E.: The Analysis of detergents and Detergent Products. London: J. Wiley & Sons. (1975).10.1016/0039-9140(75)80001-4Search in Google Scholar

42. Cui, Z. G., Yang, L. L., Cui, Y. Z. and Binks, B. P.: Langmuir.26 (2010) 4717. 10.1021/la903589eSearch in Google Scholar PubMed

43. Besergil, B.: Ind. Eng. Chem. Re.29 (1990) 667. 10.1021/ie00100a027Search in Google Scholar

44. Xia, H. F., LiuR.Q., JuY., LiuC.D. and Wang, Y. T.: Journal of Daqing Petroleum Institute.30 (6) (2006) 24. (Ch.)Search in Google Scholar

45. Wang, Z. Q., Xia, H. F., Wang, G., LiX.: Journal of Daqing Petroleum Institute. 31 (3) (2007) 25. (Ch.)Search in Google Scholar

46. Wang, G., Wang, D. M., Xia, H. F., Ju, Y.: Acta Petrol EI Sinica28 (4) (2007) 86. (Ch.)Search in Google Scholar

47. Xia, H. F., Zhang, X. C., Ma, W. G. and Wang, G.: Journal of Xian Shiyou University23 (6) (2008) 55. (Ch.)Search in Google Scholar

48. Xia, H. F., Wang, G., Ma, W. G., Liu, C. D. and Wang, Y. W.: Acta Petrol EI Sinica29 (1) (2008) 106. (Ch.)Search in Google Scholar

49. Li, C. X., Zhang, X. C., Liu, R. Q. and Ma, W. G.: XinJiang Petroleum Geology30 (2) (2009) 241. (Ch.)Search in Google Scholar

Received: 2010-10-20

Published Online: 2013-04-11

Published in Print: 2011-09-01

Synthesis of Dodecyl Lauroyl Benzene Sulfonate and its Application in Enhanced Oil Recovery

Abstract

Kurzfassung

References

Journal and Issue

Articles in the same Issue