Organic Chemistry Lab CHE1215L – Monday Section

Prof. Irina Catrina

Student: Daniel Elfenbein
Submitted: 10/28/019

Purification of Fluorene by Recrystallization and Wash

Abstract
Fluorenone contaminated fluorene was purified by recrystallization using menthol as a
solvent. The percent yield of the recovered crystals was 50.3% and the melting point increased
from 103-109C in the original sample to 115-116C after recrystallization. Attempts to purify
fluorene dissolving it in methyl tert-butyl ether and washing with water were not very effective.
Crystals after the wash were still yellow, indicating the presence of fluorenone. Crystal violet
was effectively extracted to dichloromethane from water and to water from methyl tert-butyl
ether from water.

Introduction
The method of recrystallization is used to remove impurities from crystalline solids. This
is done by dissolving the solid in a minimal amount of hot solvent. The solution is then allowed
to cool slowly, which promotes the formation of pure crystals and allows impurities to return to
the solution. The choice of solvent used depends on the solid being purified, but in general, polar
solvents should be used for polar solids and nonpolar solvents should be used for nonpolar
solids. In addition, the solid should ideally have high solubility in the hot solvent and minimal
solubility in the cold solvent.1
An extraction is a technique which takes advantage of the differing solubilities of a solute
in a pair of solvents in order to extract the solute from one to the other. The two solvents must be
immiscible with each other so that they can be separated after the extraction is performed.
Whether a given solute can be extracted from one solvent to another depends on the distribution
coefficient, which is the ratio of the solubility of the first solvent to that of the second. A wash is
almost the same as an extraction, except impurities are removed from a solution and the desired
solute stays in the original solution, as opposed from extracting the desired solute to a different
solvent.1
 In this experiment, fluorene which was contaminated with fluorenone was purified with
two different techniques: recrystallization and by a wash. Other washes and extractions were also
performed.

Experimental Procedure
A sample of fluorene which was contaminated with fluorenone was obtained and 0.764-g
was weighed out and dissolved in 30-mL boiling menthol. The flask was swirled, and small
amounts of boiling menthol were added until the solid was completely dissolved. The solution
was allowed to cool for roughly 15 minutes and then placed in an ice bath for an additional 20
minutes. The crystals which formed were recovered by vacuum filtration. The crystals were
rinsed with cold menthol and left to dry on the vacuum for 15 minutes. The recrystallized
fluorene was weighed, and its melting point was determined.
10-ml of 0.0001% aqueous crystal violet was obtained and extracted with two 5.0-mL
portions of methylene chloride.
A 30mg of fluorene which had been contaminated with crystal violet was dissolved in
25mL of methyl tert-butyl ether and washed with two 10-mL portions of water.
0.180-g fluorene from the same sample as used in the recrystallization was weighed and
dissolved in 25-mL methyl tert-butyl ether. The solution was then washed with two 10-mL
portions of water. The organic phase was collected into an Erlenmeyer flask and dried with
anhydrous magnesium. Roughly 2-mL of the solution was placed on a watch glass and allowed
to dry. The solid left on the watch glass was collected in a capillary tube and the melting point
was measured.

Results and Discussion

The yield from the recrystallization was 0.384-g, giving a percent yield of 50.3%. The
percent yield could possibly increase if the recrystallization method is refined. Possible
improvements include using less solvent and cooling the solution more slowly. The melting point
range was recorded as 115-116C. This is compared to the melting point of the original sample
(103-109C) and the literature value for the melting point of fluorene (116-117C).2 The increase
in melting point indicates that the fluorene was purified. The absence of impurities strengthens
the intermolecular forces in the crystalline structure which causes the melting point to be higher.
The melting point range for the fluorene which was washed was 108-111C. This
indicates that, although it may have been purified slightly, it was not purified to the same extent
as in the recrystallization. This was also clear based on the color of the respective samples.
Fluorenone has a yellow color, and the crystals from the wash had a yellow tinge, while the
crystals from the recrystallization were white. A possible explanation for this is that the
distribution coefficient for fluorenone in a methyl tert-butyl ether solution is too high for it to be
washed effectively with water.
In the crystal violet extraction, it was clear from the violet color in the organic phase that
the crystal violet was effectively extracted from the aqueous solution to dichloromethane.
Similarly, in the wash, crystal violet was washed from the methyl tert-butyl ether solution to the
water. This indicates that crystal violet has a relatively high distribution coefficient when
dichloromethane is used as a solvent and a relatively low distribution coefficient when methyl
tert-butyl is used as a solvent.

References
1. Mohrig, J. R.; Hammond, C. N.; Schatz, P. F.; Techniques in Organic Chemistry, 3rd ed.;
W. H. Freeman: New York, 2010; pp 114-116, 183-187.
2. Cameo Chemicals Database: https://cameochemicals.noaa.gov/chemical/16214 (accessed
10/27/2019)