Experiment:

Date:

Recrystallization

9/15/15

Name

Partners

Katheryn Soto

N/A

Drawer No.

Course / Section

#21

CHEM
315/204

Purpose:
The purpose of this experiment is to purify and isolate a solid organic compound by recrystallization
with an appropriate organic solvent and vacuum filtration.

Experiment:

Date:

Recrystallization

9/15/15

Name

Partners

Katheryn Soto

N/A

Drawer No.

Course / Section

#21

CHEM
315/204

Approach:
Determine an appropriate organic solvent (water, methanol, or petroleum ether) for recrystallization
of fluorene. Determine the mass of the impure fluorene sample by weighing. Recrystallize impure
fluorene sample using the appropriate solvent. Isolate recrystallized fluorene by vacuum filtration.
Air-dry the isolated fluorene sample for one week. Determine the mass of the purified fluorene sample
by weighing. Calculate the percent recovery for the recrystallization. Determine the melting point of
the purified fluorene sample using the Mel-Temp device.
References
Text
Pavia, D.L., Lampman, G.M., Kriz, G.S., Engel, .G.R., 2011, Introduction to Organic Laboratory
Techniques, A Small Scale Approach, GMU Edition, Chem 315/318, Cengage Learning: pp. 598608; pp. 630-642; pp. 662-680
Slayden, S., Stalick, W., Roth, R, 2014, Organic Chemistry Laboratory Manual, 2nd Edition:
Pearson Custom Publishing: pp. 31-34
Web Site URL
Dr Schornicks Website: http:/mason.gmu.edu/~jschorni/recrystallization
Vacuum Filtration Image: https://upload.wikimedia.org/wikipedia/commons/thumb/d/da/Vacuumfiltration-diagram.png/622px-Vacuum-filtration-diagram.png
Compound
2,2-Methylenebiphenyl (9H-Fluorene), CAS No. 86-73-7, CRC Handbook of Chemistry & Physics,
84th Edition, Lide, D.R., Editor-in-chief, 2003-2004, CRC Press, #5343, p. 3-272.

Experiment:

Date:

Recrystallization

9/15/15

Name

Partners

Katheryn Soto

N/A

Proc # 1

Determine Solvent

Materials

0.05g
fluorene

Solvents

methanol

water

petroleum
ether

2 Beakers
2 Hot plates
Eye dropper
3 small test tubes
Test tube rack
Spatula
3 thermometers

Desc:

Course / Section

#21

CHEM
315/204

Results
Equipment

Drawer No.

Fill 2 beakers halfway full with water.

Place a thermometer in each water bath.
Heat one water bath on a hot plate to 65oC.
Heat the second water bath on a hot plate
o
to 95 C.

Label three test tubes, one for each of the

solvents

Add 50mg of fluorene to each test tube.

Add 0.5mL (10 drops) of each solvent to

each of the appropriately labeled test tubes.

Swirl each mixture using a clean dry

spatula.

If the fluorene is very soluble or very

insoluble at room temperature in any of the
solvents, it is not suitable for recrystallization.

Choose the test tube containing the solvent

in which fluorene is slightly soluble at room
temperature and place it in the water bath of the
appropriate temperature (see chart on right).

Insert a thermometer into the test tube to

monitor the temperature.

Heat mixture to solvent boiling point (see

chart on right) and remove from bath immediately
to reduce evaporation.

If solid sample remains, use a dropper to

add solvent sparingly to the test tube until
dissolved completely dissolved (max 2.0 mL total
solvent). Continue to heat the mixture.

Unk No.

The boiling point (B.P.) of the solvent

must be less than the melting point (M.P.) of
the sample

Solvent

Formula

Polarity

Methanol
Water

CH4O
H2O

Polar
Very
polar
Non
polar

B.P.
(oC)
64.7
100

Bath
(oC)
65
95

Petroleu
C6H14
42-62 65
m ether
Tube #1
Mass Fluorene: 0.045g
Solvent:
H2O
@R.T.:
Very insoluble. All of
sample settled at the
bottom of the tube with
agitation
Good Solvent?: NO

Experiment:

Date:

Recrystallization

9/15/15

Name

Partners

Katheryn Soto

N/A

If solid sample remains, choose a different

solvent.

If almost dissolved remove the sample from

the hot water bath and cool at room temperature.

Cool the sample in an ice bath 1 min to

crystallize.

If recrystallization does not occur scratch

the surface of the mixture with a stirring rod to
encourage the process.

If still no recrystallization occurs, restart

this process of heating, cooling and scratching.

If still no crystals form, choose a different

solvent.

Tube #2
Mass Fluorene:
Solvent:
@R.T.:
Good Solvent?:
Tube #3
Mass Fluorene:
Solvent:
@R.T.:

Equation Setup:

Good Solvent?:

Drawer No.

Course / Section

#21

CHEM
315/204

0.062g
Petroleum ether
Very soluble. Sample
dissolved completely
without agitation.
NO
0.057g
Methanol
Slightly soluble.
Particles suspended but
did not dissolve
completely with
agitation.
YES

*@R.T.= at room temperature

Observations:

Methanol was chosen as the most

suitable solvent for recrystallization because
it is important that the solid be insoluble at
room temperature but soluble when heated.

Fluorine dissolved in methanol @ 65oC.

No additional solvent was needed.

Experiment:

Date:

Recrystallization

9/15/15

Name

Partners

Katheryn Soto

N/A

Proc # 2

Mass Impure Fluorene

Materials

1.5 g fluorene
Weigh boat

Equipment

Electronic
balance (0.001)

1 125 mL
Erlenmeyer flask

Spatula

Place a clean dry weigh boat on the

electronic balance and close doors.

Tare the instrument.

Use a spatula to add 1.5g of fluorene to

the weigh boat.

Record the sample mass to the precision

limit of the balance (0.001) and dispense into a
clean dry 125 mL Erlenmeyer flask.
Equation Setup:

Course / Section

#21

CHEM
315/204

Results

Desc:

Drawer No.

Mass Fluorene (g):

1.521g

Observations: Fine white powder, difficult to weigh

accurately because stuck easily to weigh boat

Experiment:

Date:

Recrystallization

9/15/15

Name

Partners

Katheryn Soto

N/A

Proc # 3

Recrystallization

1.521g fluorene
Previously
determined solvent
(methanol)

Ice bath

Equipment

1 125 mL
Erlenmeyer flask

Hotplate

Beaker

Thermomet
er

Desc:

Add the solvent chosen (methanol) to the

Erlenmeyer flask containing the fluorene
sample. Use only enough to cover the sample.

Swirl the flask to stir.

Heat the solution for 1 min. to dissolve

the fluorene.

If solid remains, add 0.5 to 1.0 mL of

solvent to the flask and continue to heat the
solution.

Repeat until a homogenous mixture has

formed.

Cool the solution to room temperature.

Transfer the flask to an ice bath to

continue cooling.

Cool the solution until it thickens but is

still fluid (slurpee consistency).

If too much recrystallization occurs, add

more methanol and repeat the recrystallization
process.

If no recrystallization occurs, reheat the

mixture to evaporate excess solvent.

Continue the process until the

appropriate solvent to crystal ratio is obtained.
Equation Setup:

Course / Section

#21

CHEM
315/204

Results

Materials

Drawer No.

Observations:
A good deal of heat and additional methanol
was required to dissolve the sample completely
(20mL total).
Temperature of water bath was increased to
75oC to aid in dissolving the sample.

Experiment:

Date:

Recrystallization

9/15/15

Name

Partners

Katheryn Soto

N/A

Proc # 4

Vacuum filtration

Filter paper
20mL
Methanol (cold)

Fluorene
solution

Equipment

#21

CHEM
315/204

Vacuum Filtration Apparatus

125 mL
Erlenmeyer flask

1 Buchner
funnel

1 Filter
flask

Rubber
tubing

Vacuum

Ring stand
and clamp

Dropper

Spatula

Desc:

Course / Section

Results

Materials

Drawer No.

Assemble the filtration apparatus (see

diagram on right).

Place the filter paper in the Buckner

funnel and moisten with a few drops of cold
methanol.

Turn on the vacuum to tightly affix the

filter paper to the funnel.

Dispense the purified fluorene solution

on top of the filter paper.

Rinse the Erlenmeyer flask with a small

amount of solvent and swirl to transfer
remaining solution to the funnel.

Filter until no more liquid can be seen

passing into the filter flask.

Add 5mL of cold methanol solvent to

the crystals to remove any remaining impurities.

Wash crystals 3 times using the cold

methanol, waiting until the filtrate stops
dripping between each wash.

Use a spatula to transfer the purified

crystals to a pre weighed vial.

Leave the lid slightly ajar to allow air

Observations:
End product before drying had larger, more
translucent white crystals and a fluffier,
flakier consistency when compared to the
impure fluorene sample.
Sample before air drying was fairly dry.

Experiment:

Date:

Recrystallization

9/15/15

Name

Partners

Katheryn Soto

N/A

Drawer No.

Course / Section

#21

CHEM
315/204

into the vial.

Air dry sample for one week.

Equation Setup:

Proc # 5

Mass Purified Fluorene

Materials

Dry purified
fluorene sample in vial

Weigh boat

Equipment

Electronic
balance (0.001)

Spatula

Calculator

Desc:

Tare the balance with all doors closed to

ensure an accurate measurement

Weigh the sample in the vial on the

electronic balance.

Record mass to three decimal places.

Subtract the previously determined mass

of the empty vial from the mass measurement to
determine the mass of the fluorene sample
Equation Setup:
Mass of vial and sample (g) mass of empty vial(g)
= mass of purified sample (g)
Mass of weigh boat and sample (g) mass of empty
weigh boat = mass of purified sample (g)

Results
Mass vial
Mass vial + sample
Mass sample

14.920g
16.335g
15.588 - 14.920 =

1.415g

Mass weigh boat

Mass boat + sample
Mass sample

2.820g
4.233g
4.233 2.820 =

1.413g

(1.415 + 1.413)/2 =

1.414g

Average

Experiment:

Date:

Recrystallization

9/15/15

Name

Partners

Katheryn Soto

N/A

Proc # 6

% Recovery

Equipment

Calculator

Similar in theory to percent yield.

Used when no chemical reaction takes place.
Determines quantity of product yielded from
the quantity of product used in the filtration process.

Equation Setup:

Course / Section

#21

CHEM
315/204

Results

Materials

Desc:

Drawer No.

% recovery = (1.414/1.521) x 100

93.0%

Grams lost = 1.521 1.414

0.107g

Experiment:

Date:

Recrystallization

9/15/15

Name

Partners

Katheryn Soto

N/A

Proc #7

Drawer No.

Course / Section

#21

CHEM
315/204

Melting Point

Results

Materials

Purified
fluorene sample

Capillary tubes

Equipment

Mel-Temp
Apparatus

Watch glass

Spatula

Thermomet
er

Glass
tubing

Desc:

Use a watch glass and spatula to crush a

small amount of purified fluorene sample.

Tap the sample with the open end of a

capillary tube to load (2mm)

Drop the capillary tube (closed end

down) through the glass tubing so the sample is
at the bottom of the tube.

Insert the capillary tube closed end down

into the Mel-Temp device.

Heat the sample increasing the

temperature 2-3oC/ min to determine the rough
melting point.

Record the 1st M.P. when the compound

begins to melt.

Record the 2nd M.P. to when the sample is

clear liquid.

Record temperatures to one decimal

place.

Cool the sample until solid.

Reheat sample until approximately 10oC

below the rough melting point.

Continue to heat the sample at a slower

rate (0.5oC/min). Record a second M.P. range.
Equation Setup:

Purified Fluorene

Avg(oC):
Observ:

1st M.P.
(oC)
113.5
112.5
113.0

2nd M.P. (oC)

118.0
116.5
117.3

Larger more flaky

translucent white
crystals, fluffy
consistency.

115.2

Experiment:

Date:

Recrystallization

9/15/15

Name

Partners

Katheryn Soto

N/A

Drawer No.

Course / Section

#21

CHEM
315/204

Summary of Results:
The solvent chosen for the recrystallization of fluorene was methanol. The mass of the impure fluorene
sample before recrystallization was 1.521g. The mass of the purified fluorene sample was 1.414g. The
percent recovery for the recrystallization of the fluorene sample was 93.0%. The average melting point
for the purified fluorene sample was 113.0-117.3oC (Average 115.2oC).

Experiment:

Date:

Recrystallization

9/15/15

Name

Partners

Katheryn Soto

N/A

Drawer No.

Course / Section

#21

CHEM
315/204

Analysis & Conclusions:

The purpose of this experiment was to purify and isolate solid fluorene by recrystallization of an
impure fluorene sample with an appropriate organic solvent and vacuum filtration.
First, three organic solvents: methanol, petroleum ether, and water were considered for fluorene
recrystallization. An appropriate solvent for recrystallization is one in which the compound of interest
is soluble at elevated temperatures, but only sparingly soluble at room temperature or lower. Since
fluorene is a nonpolar organic compound, a polar solvent is the best bet for crystallization. In
petroleum ether, a nonpolar organic solvent, fluorene was too soluble at room temperature,
demonstrating the like-dissolves-like rule of chemistry. In water, a very polar organic solvent,
fluorene was insoluble both at room temperature and at elevated temperatures. In methanol, fluorene
was slightly soluble at room temperature, but very soluble when heated. Methanol is polar; however,
because it is an alcohol, it contains both polar and nonpolar parts, which causes both polar and
nonpolar substances to be soluble in it.
The recrystallization was carried out using methanol as the solvent. After recrystallization of the
compound, the sample was isolated from the mother liquor via vacuum filtration and allowed to air
dry. After one week, the air-dried sample was weighed (1.414g) and the percentage recovery for the
recrystallization was calculated (93%). The large percent recovery suggest careful lab technique was
used in transferring the sample from container to container as to prevent additional loss
As with any recrystallization, it is impossible to achieve 100% product recovery due to the fact that
some of the fluorene sample is soluble in the methanol solvent at any temperature; therefore, some
fluorene remained dissolved in the mother liquor during filtration (0.107g of the 1.521g before
recrystallization). To increase the percent recovery in future trials, a second recrystallization can be
performed with the mother liquor by evaporation; however, this second recrystallization will produce a
less pure product (marked by a lower and broader melting point) by comparison to the first due to a
higher concentration of impurities after evaporating the solvent.
Finally, the purity of the isolated fluorene was determined by testing its melting point (113.0-117.3 oC;
avg. 115.2oC). The melting point of the purified sample was very close to the literature value of
114.8oC, suggesting a fairly pure final product. In comparison to the impure product, the purified
fluorene was fluffy, with larger more flaky crystals.

Experiment:

Date:

Recrystallization

9/15/15

Name

Partners

Katheryn Soto

N/A

Drawer No.

Course / Section

#21

CHEM
315/204

Literature Summary (Unknowns, Synthesized Compounds)

Unknown No.
CAS No.

86-73-7

Name (IUPAC)

2,2Methylenebiphenyl

Synonyms

9H-Fluorene,
Fluorene,
diphenylenemethan
e, oBiphenylenemethan
e

Melting Point
(oC)

Lit (113.0116.0oC) 114.8oC

Exp (113.0117.3oC) 115.2oC

Lit
Exp

Lit
Exp

Lit
Exp

Boiling Point
(oC)

Lit 294.0oC
Exp

Lit
Exp

Lit
Exp

Lit
Exp

Refractive Index
(nD20)

Lit 1.645
Exp

Lit
Exp

Lit
Exp

Lit
Exp

Solubility
(Rel to Water)

Lit 800g/L @ 25
Exp

Lit
Exp

Lit
Exp

Lit
Exp

Density
Rel to Water

Lit 1.203g/cm-3
Exp

Lit
Exp

Lit
Exp

Lit
Exp

Molecular
Formula

C13H10

Experiment:

Date:

Recrystallization

9/15/15

Name

Partners

Katheryn Soto

N/A

Structural
Formula

Drawer No.

Course / Section

#21

CHEM
315/204