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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

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, γcmc 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, γcmc, 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.


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:

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.


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Received: 2010-10-20
Published Online: 2013-04-11
Published in Print: 2011-09-01

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