In the Laboratory
Recycling Solvent Mixtures of Ethyl Acetate and Hexanes
Timothy J. Wilkinson
Department of Chemistry, Wheaton College, Wheaton, IL 60187
As part of an organic experiment we have used flash
chromatography (1, 2) to purify 1,1′-diacetylferrocene (3).
This experiment, and many TLC analyses during the year,
produces a sizable amount of ethyl acetate–hexanes waste.
Though these solvents are not easily separated by distillation1
they may be recovered as a mixture by distillation. The
composition of the mixture is conveniently estimated2 by
developing a TLC plate3 of acetylferrocene and/or 1,1'-
diacetylferrocene with the mixture,4 determining the R f’s, and
reading the percentage composition from a graph (see figure)
1640 Journal of Chemical Education • Vol. 75 No. 12 December 1998 • JChemEd.chem.wisc.edu
obtained by plotting R f ’s of acetylferrocene and 1,1′-
diacetylferrocene vs solutions of known ethyl acetate–hexanes
composition. To reuse the mixture for column or thin-layer
chromatography, a calculated amount of additional ethyl
acetate or hexanes (eq 1)5 is added to a given amount of the
mixture to achieve the desired composition. In this equation,
y is milliliters of ethyl acetate or hexanes added to achieve
the desired composition; a is milliliters of the ethyl acetate–
hexanes mixture; n is the percent of ethyl acetate or hexanes
in the mixture; and z is the desired percent of ethyl acetate
or hexanes.
a z–n
y= (1)
100 – z
Notes
1. The boiling points of ethyl acetate (77 °C) and hexanes (69 °C)
are too close for separation by a simple distillation.
2. The refractive indexes of ethyl acetate (1.3720) and hexanes
(1.3790) are too close for an accurate percentage determination by
refractometry.
3. Silica-gel TLC plates (Aldrich Z12, 278-5).
4. Dried over CaCl2.
5. The derivation of eq 1 can be used as an exercise.
Literature Cited
1. Bell, W. L.; Edmondson, R. D. J. Chem. Educ. 1986, 63, 361.
2. Shusterman, A. J.; McDougal, P. G.; Glasfeld, A. J. Chem. Educ.
1997, 74, 1222.
3. Bublitz, D. E.; Rinehart, K. L., Jr. Org. Reactions 1969, 17, 1.