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  Home > JCE Print > Journal of Chemical Education > Issues > 2002  > June  >
In the Laboratory
Synthesis and Characterization of a Gasoline Oxygenate, Ethyl tert-Butyl Ether
Craig J. Donahue, Teresa D'Amico, and Jennifer A. Exline
Department of Natural Sciences, University of Michigan-Dearborn, Dearborn, MI 48128-1491
Cover
June 2002
Vol. 79 No. 6
p. 724
Abstract
A laboratory procedure involving the synthesis and characterization of ethyl tert-butyl ether (ETBE) is described. This experiment has been used in a general chemistry sequence that includes a section on organic chemistry, but is also well suited for an introductory organic chemistry laboratory course. ETBE is prepared by the acid-catalyzed reaction of tert-butyl alcohol with ethyl alcohol. The product is recovered as a low-boiling azeotrope and purified by liquid–liquid extraction with water. By using gas chromatography and IR spectroscopy to examine both the crude and the purified products, students can see how much the purity of their sample improves. They can also appreciate the value of these methods (especially GC) as tools to establish purity. Student results are presented. The use of ETBE and its more prominent cousin methyl tert-butyl ether (MTBE) as gasoline oxygenates has become very controversial because they have polluted underground water supplies. This lab permits students to prepare a compound that has a real use and regularly makes headlines in the news. This lab experiment is part of an effort to develop a general chemistry sequence for engineering students using the theme of "Chemistry and the Automobile".
Supplement
Detailed instructions for students, with worksheets and diagrams of the experimental setups, are available.
*  Contents JCE 2002p0724.wpd (Word Perfect)
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*  Citation
 Donahue, Craig J.; D'Amico, Teresa; Exline, Jennifer A. J. Chem. Educ. 2002 79 724.
*  Keywords
 Chromatography; Environmental Chemistry; General Chemistry; Laboratory Instruction; Organic Synthesis
*  History
 Created:
Last Updated:		 May 17, 2002
March 16, 2005
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