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The Chemical Educator

ISSN: 1430-4171 (electronic version)

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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,
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

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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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