Experiment 10: A Separation and Purification Scheme

Name: Colin Kenney

Date: June 16, 2015
Prelab / Abstract
The purpose of this experiment was to devise a purification and separation scheme for a
certain three component mixture. The mixture under study was 50% o-toluic acid, 40%
fluorene, and 10% 1,4 dibromobenzene. The following reagents were available for use
during this experiment: 1 M sodium hydroxide, 6 M sodiumhydroxide, 1 M hydrochloric
acid, 6 M hydrochloric acid, 1 M sodium bicarbonate, saturated sodium chloride, diethyl
ether, 95% ethanol, methanol, isopropyl, alcohol, acetone, hexane, toluene, methylene,
chloride, and granular anhydrous sodium sulfate. The goal of this experiment was to use
these reagents, as well as techniques and procedueres from previous labs, and isolate two
of the three compounds contained in the mixture with as high yield as possible.
Procedure
Approximately 0.5 grams of the mixture was weighed and the mass recorded. To
dissolve the mixture, it was mixed with 4 mL of methylene chloride. The solution was
centrifuged and liquid was transferred to a second tube. The solid that remained, 1,4
dibromobenzene, was then weighed and recorded. The liquid was then washed with two 4
mL portions of 1 M sodium hydroxide. After each washing, the top aqueous layer was
removed with a filter-tip pipet and moved into a beaker. Then 6 M HCl was added to the
beaker until the pH was approximately 1-2. The solution was stirred and cooled in an ice
bath for five minutes before being vacuum filtrated. The solid, o-toluic acid, was then
dried in the oven and its mass was recorded.
To the centrifuged liquid, anhydrous sodium sulfate was added and the solution
was shaken before sitting for five minutes. The liquid was then transferred to a beaker
and the liquid was evaporated in a warm water bath. The mass of the solid that remained,
fluorene, was then recorded.
Finally, the melting points of the final two solids were measured and recorded.
Materials
2 centrifuge tubes
4 mL methylene chloride
8 mL 1 M NaOH
2 filter-tip pipets
1-2 mL 6 M HCl
Erlenmeyer flask
Funnel and filter paper
Large beaker for ice bath
Heating plate
1 small beaker
Data and Calculations
Weight of unkown: 0.5095 g
Weight of centrifuge tube 1: 3.6278 g

Weight of tube 1 and 1,4 dibromobenzene: 3.6748

Weight of watch glass and filter paper: 58.7191 g
Weight of watch glass, filter paper, and o-toluic acid: 58.9592 g
Weight of beaker: 21.0387
Weight of beaker and fluorene: 21.2249
Weight of 1,4 dibromobenzene = 3.6748 g 3.6728 g = 0.047 g
Weight of o-toluic acid = 58.9592 g - 58.7191 g = 0.2401 g
Weight of fluorene = 21.2249 - 21.0387 = 0.1862 g
Theoretical yields:
o-toluic acid = (0.5)(0.5095) = 0.2548
fluorene = (0.4)(0.5095) = 0.2038
1,4 dibromobenzene = (0.1)(0.5095) = 0.05095
Percent recovery = (0.047 + 0.2401 + 0.1862) / 0.5095 = 92.95%
Percent composition:
Percent o-toluic acid = 0.2401/ 0.5095 = 47.12%
Percent fluorene = 0.1862 / 0.5095 = 36.55%
Percent 1,4 dibromobenzene = 0.047 / .5095 = 9.2%
Percent yield:
o-toluic acid = 0.2401 / 0.2548 = 94.23%
fluorene = 0.1862 / 0.2038 = 91.36%
1,4 dibromobenzene = 0.047 / 0.05095 = 92.30%
Melting point ranges:
o-toluic acid = 101-103 C
fluorene = 110 114 C
Results
The three components of this mixture, o-toluic acid, 1,4 dibromobenzene, and fluorene
were obtained with a 92.95% recovery. The three respective components were also
recovered with decently high yields of 94.23%, 91.36%, and 92.30%. The melting point
ranges of o-toluic acid and fluorene were measured to be 101-103 C and 110-114 C,
respetively. The three compounds were all white solids.
Conclusion
The purpose of this experiment was to devise an experimental procedure and separation
scheme for a three component mixture of o-toluic acid, fluorene, and 1,4
dibromobenzene. To a great extent, the purpose of this exerpiment was met as the devised
procedure was succesful in identifying and separating the three components in this
mixture. The separation of the compounds is corrborated by the fact that accurate melting
point ranges for o-toluic acid and fluorene were obtained. The true melting points for otoluic aid and fluorene are 104-105 C and 116 C respectively, which are close to the
measured melting points of 101-103 C and 110-114 C. This indicates that the obtained
compounds, although not completely pure, were separated with relatively low impurities.