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As part of an organic experiment we have used flash obtained by plotting R f ’s of acetylferrocene and 1,1′-
chromatography (1, 2) to purify 1,1′-diacetylferrocene (3). diacetylferrocene vs solutions of known ethyl acetate–hexanes
This experiment, and many TLC analyses during the year, composition. To reuse the mixture for column or thin-layer
produces a sizable amount of ethyl acetate–hexanes waste. chromatography, a calculated amount of additional ethyl
Though these solvents are not easily separated by distillation1 acetate or hexanes (eq 1)5 is added to a given amount of the
they may be recovered as a mixture by distillation. The mixture to achieve the desired composition. In this equation,
composition of the mixture is conveniently estimated2 by y is milliliters of ethyl acetate or hexanes added to achieve
developing a TLC plate3 of acetylferrocene and/or 1,1'- the desired composition; a is milliliters of the ethyl acetate–
diacetylferrocene with the mixture,4 determining the R f’s, and hexanes mixture; n is the percent of ethyl acetate or hexanes
reading the percentage composition from a graph (see figure) 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.