Synthesis of Alkylbenzene from Medium-Chain Olefins Catalyzed by an Acidic Ionic Liquid and the Surface Properties of Their Sulfonate

Shanshan Kong; Lei Li; Chen Chen; Xu Li; Lei Liu; Jinxiang Dong

doi:10.3139/113.110670

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Synthesis of Alkylbenzene from Medium-Chain Olefins Catalyzed by an Acidic Ionic Liquid and the Surface Properties of Their Sulfonate

Shanshan Kong , Lei Li , Chen Chen , Xu Li , Lei Liu und Jinxiang Dong

Veröffentlicht/Copyright: 9. März 2020

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Aus der Zeitschrift Tenside Surfactants Detergents Band 57 Heft 2

Abstract

The Fischer-Tropsch synthesis can be used to achieve a high content of α-olefin (C₅–C₁₁) products using Fe-based catalysts. Herein, C₆ and C₈ α-olefins have been selected as examples for the alkylation of benzene catalyzed by using an acidic ionic liquid (Et₃NHCl-AlCl₃) to obtain a variety of intermediates used to prepare surfactants. A series of alkylbenzenes were synthesized by controlling the reaction conditions and their corresponding alkylbenzene sulfonates were successfully obtained by sulfonation and neutralization. It was found that the single chain alkylbenzene sulfonate derivatives did not display typical surfactant properties due to their short hydrophobic chain length. However, double chain alkylbenzene sulfonates exhibit excellent surfactant properties, and decrease the water surface tension compared to commercially available sodium dodecylbenzene sulfonates. A γ_cmc (mN m⁻¹) value of 32.70 was observed for sodium di-hexylbenzene sulfonates, 29.98 for sodium di-octylbenzene sulfonates, and 36.0 for sodium dodecylbenzene sulfonates. In addition, double chain alkylbenzene sulfonates show an improved emulsifying and wettability performance compared to sodium dodecylbenzene sulfonate. This demonstrates that the capability of alkylbenzene sulfonate to decrease the surface tension are closely related to the total carbon number of side chain-alkyl groups connected to the benzene ring.

Kurzfassung

Die Fischer-Tropsch-Synthese lässt sich einsetzen, um unter Verwendung von Katalysatoren auf Fe-Basis einen hohen Gehalt an α-Olefin (C₅–C₁₁)-Produkten zu erzielen. Für diese Untersuchung wurden C₆- und C₈-α-Olefine als Beispiele für die Alkylierung von Benzen ausgewählt, die durch die Verwendung einer sauren ionischen Flüssigkeit (Et₃NHCl-AlCl₃) katalysiert wurde, wobei eine Vielzahl von Zwischenprodukten erhalten wird, die für die Herstellung von Tensiden verwendet werden. Eine Reihe von Alkylbenzenen wurde durch Kontrolle der Reaktionsbedingungen synthetisiert; ihre entsprechenden Alkylbenzensulfonate wurden erfolgreich durch Sulfonierung und Neutralisation erhalten. Es wurde gefunden, dass die einkettigen Alkylbenzensulfonat-Derivate aufgrund ihrer kurzen hydrophoben Kettenlänge keine typischen Tensideigenschaften zeigten. Die doppelkettigen Alkylbenzensulfonate zeigen jedoch ausgezeichnete Tensideigenschaften, wodurch die Wasseroberflächenspannung im Vergleich zu den im Handel erhältlichen Natriumdodecylbenzensulfonaten verringert wird. Für Natriumdihexylbenzensulfonat wurde ein γ_CMC-Wert von 32,70 mN m⁻¹ beobachtet, für Natriumdioctylbenzensulfonat 29,98 mN m^–1 und für Natriumdodecylbenzensulfonat 36,0 mN m^–1. Darüber hinaus zeigen die doppelkettigen Alkylbenzensulfonate im Vergleich zu Natriumdodecylbenzensulfonat ein verbessertes Emulgier- und Benetzbarkeitsverhalten. Dies zeigt, dass die Fähigkeit von Alkylbenzensulfonaten, die Oberflächenspannung zu verringern, eng mit der Gesamtkohlenstoffzahl der an den Benzenring gebundenen Alkylgruppen-Seitenketten zusammenhängt.

Key words: Alkylbenzene sulfonates; ionic liquid; α-olefins; synthesis; properties

Stichwörter: Alkylbenzolsulfonate; ionische Flüssigkeit; α-Olefine; Synthese; Eigenschaften

∗ Correspondence address, Prof. Dr. Lei Liu, Mr. Xu Li, College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan, Shanxi 030024, China, E-Mail: liulei@tyut.edu.cn, lixu02@tyut.edu.cn

Shanshan Kong is a M.D. student in the College of Chemistry and Chemical Engineering at Taiyuan University of Technology and her research involves the purification and characterization of anionic surfactant.

Lei Li is a M.D. student in the College of Chemistry and Chemical Engineering at Taiyuan University of Technology and his research involves the synthesis and application of lubricants.

Chen Chen is a Ph.D. student in the College of Chemistry and Chemical Engineering at Taiyuan University of Technology and her research involves the synthesis and application of lubricants.

Xu Li is a teacher of the College of Chemistry and Chemical Engineering at Taiyuan University of Technology and his research involves synthesis and application of fine chemicals.

Lei Liu is a Professor of the College of Chemistry and Chemical Engineering at Taiyuan University of Technology and he is the winner of excellent youth. His research involves catalytic chemistry as well as synthesis and application of fine chemicals.

Jinxiang Dong is Professor and dean of the College of Chemistry and Chemical Engineering at Taiyuan University of Technology. He won the National Science Fund for Distinguished Young Scholars. His research involves daily washings.

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Received: 2019-10-01

Accepted: 2019-12-01

Published Online: 2020-03-09

Published in Print: 2020-03-16

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https://doi.org/10.3139/113.110670

Schlagwörter für diesen Artikel

Alkylbenzene sulfonates; ionic liquid; α-olefins; synthesis; properties