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The Chemical Educator
ISSN: 1430-4171 (electronic version)
Abstract Volume 15
(2010) pp 376-380
Room Temperature Ionic Liquid for Olefin Metathesis: an Undergraduate Laboratory Experiment
Megumi Fujita
Department of Chemistry, University of West Georgia,
1601
Maple Street, Carrollton, GA 30118, mfujita@westga.edu
Received April 28, 2010.
Accepted July 17, 2010.
Published: 12 December 2010
Abstract. As a teaching tool for green chemistry and organometallic chemistry, the olefin metathesis reaction catalyzed by Grubbs catalysts in a room temperature ionic liquid (RTIL) was adapted to our upper level laboratory class. This lab introduces several key concepts in green chemistry; general philosophy and the importance of “green” alternatives to volatile organic solvents, catalysis, and recycling of catalysts. The organometallic concepts include metal carbene complexes, electron-counting, type of organometallic reactions and the reaction mechanism of olefin metathesis. Olefin metathesis is also concurrently taught in a co-requisite lecture course, Advanced Inorganic Chemistry. Students carried out styrene self-cross metathesis in two different RTILs: [BMIM]PF6 and [BMIM]BF4 (BMIM = 1-butyl-3-methylimidazolium). Students also compared two types of Grubbs-Hoveyda second generation catalysts. The lab included miscibility tests of RTILs with various solvents to find their general solubility behavior.
Key Words: Laboratories and Demonstrations; organic chemistry; organometallic chemistry
(*) Corresponding author. (E-mail: mfujita@westga.edu)
Article in PDF format (121 KB) HTML format
Supporting Materials:
The laboratory handout for students (including experimental procedures and post-lab questions) and product spectroscopic information (1H NMR spectrum of E-stilbene in DMSO-d6) are available (47 KB)
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