Synthesis of Petroleum Sulfonate Surfactant by Different Sulfonating Agent with Application of HIGEE Technology

›› 2010, Vol. 18 ›› Issue (5): 848-855.

• PRODUCT ENGINEERING AND CHEMICAL TECHNOLOGY • Previous Articles Next Articles

Synthesis of Petroleum Sulfonate Surfactant by Different Sulfonating Agent with Application of HIGEE Technology

ZHANG Di, ZHANG Pengyuan, ZOU Haikui, CHU Guangwen, WU Wei, ZHU Zhongwu, SHAO Lei, CHEN Jianfeng

Research Center of the Ministry of Education for High Gravity Engineering and Technology, Beijing University of Chemical Technology, Beijing 100029, China

Received:2010-04-16 Revised:2010-06-29 Online:2010-10-28 Published:2010-10-28
Supported by:
Supported by the National Natural Science Foundation of China (20821004, 20990221);the National High Technology Research and Development Program of China (2006AA030202)

Synthesis of Petroleum Sulfonate Surfactant by Different Sulfonating Agent with Application of HIGEE Technology

张迪, 张鹏远, 邹海魁, 初广文, 毋伟, 朱忠武, 邵磊, 陈建峰

Research Center of the Ministry of Education for High Gravity Engineering and Technology, Beijing University of Chemical Technology, Beijing 100029, China

通讯作者: CHEN Jianfeng,E-mail:chenjf@mail.buct.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China (20821004, 20990221);the National High Technology Research and Development Program of China (2006AA030202)

Abstract

Abstract: With the application of HIGEE process intensification technology, petroleum sulfonate surfactant used for enhanced oil recovery was synthesized from petroleum fraction of Shengli crude oil with three sulfonating agents, including diluted liquid sulfur trioxide, diluted gaseous sulfur trioxide and fuming sulfuric acid. For each sulfonating agent, different operation modes (liquid-liquid or gas-liquid reaction with semi-continuous or continuous operation) were applied. The effects of various experimental conditions, such as solvent/oil mass ratio, sulfonating agent/oil mass ratio, gas/liquid ratio, gas concentration, reaction temperature, rotating speed, circulation ratio, reaction time and aging time, on the content of active matter and unsulfonated oil were investigated. Under relatively optimal reaction conditions, the target product was prepared with high mass content of active matter (up to 45.3%) and extremely low oil/water interfacial tension (4.5×10^-3mN·m^-1). The product quality and process efficiency are higher compared with traditional sulfonation technology.

Key words: sulfonation, petroleum sulfonate, sulfonating agent, high gravity technology, rotating packed bed

摘要： With the application of HIGEE process intensification technology, petroleum sulfonate surfactant used for enhanced oil recovery was synthesized from petroleum fraction of Shengli crude oil with three sulfonating agents, including diluted liquid sulfur trioxide, diluted gaseous sulfur trioxide and fuming sulfuric acid. For each sulfonating agent, different operation modes (liquid-liquid or gas-liquid reaction with semi-continuous or continuous operation) were applied. The effects of various experimental conditions, such as solvent/oil mass ratio, sulfonating agent/oil mass ratio, gas/liquid ratio, gas concentration, reaction temperature, rotating speed, circulation ratio, reaction time and aging time, on the content of active matter and unsulfonated oil were investigated. Under relatively optimal reaction conditions, the target product was prepared with high mass content of active matter (up to 45.3%) and extremely low oil/water interfacial tension (4.5×10^-3mN·m^-1). The product quality and process efficiency are higher compared with traditional sulfonation technology.

关键词: sulfonation, petroleum sulfonate, sulfonating agent, high gravity technology, rotating packed bed

ZHANG Di, ZHANG Pengyuan, ZOU Haikui, CHU Guangwen, WU Wei, ZHU Zhongwu, SHAO Lei, CHEN Jianfeng. Synthesis of Petroleum Sulfonate Surfactant by Different Sulfonating Agent with Application of HIGEE Technology[J]. , 2010, 18(5): 848-855.

张迪, 张鹏远, 邹海魁, 初广文, 毋伟, 朱忠武, 邵磊, 陈建峰. Synthesis of Petroleum Sulfonate Surfactant by Different Sulfonating Agent with Application of HIGEE Technology[J]. CIESC Journal, 2010, 18(5): 848-855.

References

1 Ma, S., Dong, M., Li, Z., Shirif, E., “Evaluation of the effectiveness of chemical flooding using heterogeneous sandpack flood test”, J. Petrol. Sci. Eng., 55, 294-300 (2007).
2 Liu, Q., Dong, M., Zhou, W., Ayub, M., Zhang, Y.P., Huang, S., “Improved oil recovery by adsorption-desorption in chemical flooding”, J. Petrol. Sci. Eng., 43, 75-86 (2004).
3 Yuan, S.Y., Quy, N.V., “Effects of the main parameters of the chemical flooding process”, J. Petrol. Sci. Eng., 3, 85-96 (1989).
4 Cayias, J.L., Schechter, R.S., Wade, W.H., “The utilization of petroleum sulfonates for producing low interfacial tensions between hydrocarbons and water”, J. Colloid Interf. Sci., 59, 31-38 (1977).
5 Hall, A.C., “Interfacial tension and phase behavior in systems of petroleum sulfonate/brine/n-alkane”, Colloid. Surface., 1, 209-228 (1980).
6 Spence, R.J., “Stirred vortex tank reactor and method of CO2 addition for producing overbased petroleum sulfonate”, U.S. Pat., 4541940 (1985).
7 Nussbaum, M.L., Knaggs, E.A., “Process for sulfonation”, U.S. Pat., 4148821 (1979).
8 Zaïd, T.A., Benmaza, K., Chitour, C.E., “Sulfonation of linear alkyl benzene (LAB) in a corrugated wall falling film reactor”, Chem. Eng. J., 76, 99-102 (2000).
9 Nussbaum, M.L., Knaggs, E.A., “Petroleum sulfonates”, U.S. Pat., 4177207 (1979).
10 Mann, R., Knysh, P., Allan, J.C., “Exothermic gas absorption with complex reaction:sulfonation and discoloration in the absorption of sulfur trioxide in dodecylbenzene”, In:Chemical Reaction Engineering, ACS Symposium Series, Boston (1982).
11 Gilbert, E., Veldhuis, B., “Sulfonation with sulfur trioxide-petroleum lubricant raffinates”, Ind. Eng. Chem., 49, 31-38 (1957).
12 Bourne, J.R., Tovstiga, G., “Micromixing and fast chemical reactions in a turbulent tubular reactor”, Chem. Eng. Res. Des., 66, 26-32 (1988).
13 Thoma, S., Ranade, V.V., Bourne, J.R., “Interaction between microand macro-mixing during reactions in agitated tanks”, Can. J. Chem. Eng., 69, 1135-1141 (1991).
14 Bourne, J.R., Gholap, R.V., Rewatkar, V.B., “The influence of viscosity on the product distribution of fast parallel reactions”, Chem. Eng. J., 58, 15-20 (1995).
15 Reddy, K.J., Gupta, A., Rama, D.P., Rao, O.P., “Process intensification in a HIGEE with split packing”, Ind. Eng. Chem. Res., 45, 4270-4277 (2006).
16 Liu, H.S., Lin, C.C., Wu, S.C., Hsu, H.W., “Characteristics of a rotating packed bed”, Ind. Eng. Chem. Res., 35, 3590-3596 (1996).
17 Chen, Y.S., Lin, F.Y., Lin, C.C., Tai, C.Y.D., Liu, H.S., “Packing characteristics for mass transfer in a rotating packed bed”, Ind. Eng. Chem. Res., 45, 6846-6853 (2006).
18 Zhao, H., Shao, L., Chen, J. F., “High-gravity process intensification technology and application”, Chem. Eng. J., 156, 588-593 (2010).
19 Chen, J.F., “A method of preparation of an anionic surfactant for enhanced oil recovery”, China Pat., 200810116805.7 (2008). (in Chinese)
20 Gilbert, E., “The reactions of sulfur trioxide, and its adducts, with organic compounds”, Chem. Rev., 62, 549-589 (1962).
21 Roberts, D.W., “Optimisation of the linear alkyl benzene sulfonation process for surfactant manufacture”, Org. Process Res. Dev., 7, 172-184 (2003).
22 Ren, M.H., Dong, L., “Synthesis and performance of a low-cost petroleum sulfonate surfactant KPS-2”, Acta Petrolei Sinica, 23, 101-105 (2002).
23 Wang, F.Q., Wang, Y.D., Wu, Y.X., Gao, M., “Synthesis and performance assessment of petroleum sulfonate for oil displacement”, Journal of China University of Petroleum, 32, 138-141 (2008). (in Chinese)
24 Zhou, M., Pu, W.F., Zhao, J.Z., “Optimization of reaction conditions for petroleum sulfonate by gas phase method”, Journal of Southwest Petroleum University, 29, 132-136 (2007). (in Chinese)
25 Xu, H.J., Xia, J.D., “Preparation of petroleum sulfonate for tertiary oil recovery”, Journal of East China University of Science and Technology, 22, 33-37 (1996). (in Chinese)
26 Baldyga, J., Bourne, J.R., “A fluid mechanical approach to turbulent mixing and chemical reaction (Ⅲ) Computational and experimental results for the new micromixing model”, Chem. Eng. Commun., 28, 259-281 (1984).

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Synthesis of Petroleum Sulfonate Surfactant by Different Sulfonating Agent with Application of HIGEE Technology

Synthesis of Petroleum Sulfonate Surfactant by Different Sulfonating Agent with Application of HIGEE Technology

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