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Colorful Chemical Demonstrations on the Extraction of Anionic Species from Water into Ether Mediated by Tricaprylylmethylammonium Chloride (Aliquat 336), a Liquid–Liquid Phase-Transfer Agent

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Patrick Gordon

Department of Chemistry, Simmons College, Boston, MA 02115-5898

Anil Joseph Pezhathinal , Kerensa Rocke , Louis Susanto , Derek Handke and Roch Chan-Yu-King

Division of Science and Physical Education, University of Science and Arts of Oklahoma, Chickasha, OK 73018

Eugene N. Losey

Department of Chemistry, Elmhurst College, Elmhurst, IL 60126

Richard L. Keiter

Department of Chemistry, Eastern Illinois University, Charleston, IL 61920-3099

J. Chem. Educ., 2006, 83 (8), p 1161

DOI: 10.1021/ed083p1161

Publication Date (Web): August 1, 2006

Abstract

Liquid–liquid phase transfer catalysis (LLPTC) plays an ever-increasing role in academic research and in the large scale industrial production of chemicals. This method involves a biphasic medium composed of water and an organic solvent in which the LLPT-catalyst plays a critical role in the transport of some water-soluble reagents (e.g., nucleophiles or bases) from water into the organic layer. This article provides a list of easy to perform and relatively safe experiments that may be used to demonstrate the extraction of some colorful water-soluble reagents by Aliquat 336 into ether. This demonstrative process serves to simulate the preliminary extractive step of an ionic species in LLPT-catalyzed reactions and introduce various undergraduate chemistry concepts and principles to students.