Experiment:

Date:

Extraction of Caffeine

10/27/15

Name

Partners

Katheryn Soto

N/A

Drawer No.

Course / Section

#21

CHEM
315/204

Purpose:
The purpose of this experiment is to extract and isolate caffeine from an over-the counter stimulant
drug via liquid-liquid extraction, recrystallization and vacuum filtration of the desired compound.

Experiment:

Date:

Extraction of Caffeine

10/27/15

Name

Partners

Katheryn Soto

N/A

Drawer No.

Course / Section

#21

CHEM
315/204

Approach:
Weigh the Vivarin tablets and Sodium carbonate with the electronic balance to determine the mass.
Prepare, heat and decant Vivarin and Sodium Carbonate solution. Use the liquid-liquid extraction
method with dichloromethane to extract and isolate caffeine from the aqueous Vivarin/sodium carbonate
solution. Add Anhydrous sodium sulfate to the extracted caffeine solution. Add cold acetone and
petroleum ether to recrystallize the dried sample. Dry further via vacuum filtration. Air-dry for one
week. Determine the mass of the purified caffeine sample by weighing. Calculate the percent recovery for
the purification. Use the MelTemp apparatus to determine the melting point and assess the purity of the
final sample.
References
Text
Slayden, S., Stalick, W., Roth, R, 2014, Organic Chemistry Laboratory Manual, 2nd Edition:
Pearson Custom Publishing: pp. 47-49
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. 24, 7384
Web Site URL
Dr Schornicks Website: http:/mason.gmu.edu/~jschorni/caffeine
Hckels Rule: http://goo.gl/rFI2Lz
Unknown or Synthesized Compound
3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione (Caffeine), CAS No. 58-08-2, CRC Handbook of
Chemistry & Physics, 84th Edition, Lide, D.R., Editor-in-chief, 2003-2004, CRC Press, #1692, p. 390.

Experiment:

Date:

Extraction of Caffeine

10/27/15

Name

Partners

Katheryn Soto

N/A

Proc # 1

Mass Reagents

2 Vivarin
tablets

8g Sodium
Carbonate (Na2CO3)

2 Weigh boats

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Results

Materials

Drawer No.

Equipment

Electroni
c balance
(0.001g)

Calculat
or

Desc:

Tare the balance.

Record the mass of the empty boat
to the nearest 0.001g.

Record the mass of the tablets in the

weigh boat to the precision limit of the
balance.

Calculate the % active ingredient

based on the grams of caffeine per pill.

Repeat steps 1-3 using 8g of

Na2CO3) and record mass to the nearest
0.001g.
Equation Setup:
Mass of Vivarin tablets:
Mass tablets in boat (g) mass empty boat (g)
= mass tablets (g)
Percent caffeine per pill:
[Caffeine per pill (g) / [Mass of 2 tablets (g) /
2]] x 100
Mass Sodium Carbonate
Mass sample in boat (g) mass empty boat (g)
= mass sample (g)

Mass weigh boat

Mass boat + tablets
Mass tablets
Caffeine/pill
% Caffeine/pill

Unk No.

Mass Vivarin
3.285g
4.180g
4.180 - 3.285

0.895g

0.200g
[.200/(0.895/2)]x100 44.7 %

Mass Na2CO3
Mass weigh boat
3.265g
Mass boat + Na2CO3
11.516g
Mass Na2CO3
11.615 3.265

8.251g

Experiment:

Date:

Extraction of Caffeine

10/27/15

Name

Partners

Katheryn Soto

N/A

Proc # 2

Prepare Solution

2 Vivarin tablets
60mL D.I. H2O
8g Sodium
Carbonate (Na2CO3)

Teflon boiling
chip

Glass wool

Equipment

Mortar &
pestle
2 150mL
Beakers

Spatula
Graduated
cylinder

Hot plate

Glass
funnel

Clay
triangles

Iron ring

Ring stand

125mL
separatory funnel

Desc:

Pulverize the Vivarin using the mortar

and pestal into a uniform powder.

Transfer the powder to a clean, dry

150mL beaker

Using a graduated cylinder measure

60mL of D.I. H2O

Add to the beaker.

Add pre-weighed 8g Na2CO3 to the

beaker.

Add Teflon boiling chip.

Heat solution on a hotplate. Boil for

2min.

Remove beaker from heat. Allow mixture

to settle.
Equation Setup:

Course / Section

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Results

Materials

Drawer No.

Observations:

Vivarin tablet was easy to crush.

Resulted in a fine white powder.

Na2CO3 was the same color as the vivarin

but was had larger crystals, and more granular
appearance.

The color of the solution changed from

colorless to yellow as it approached a boil.

Experiment:

Date:

Extraction of Caffeine

10/27/15

Name

Partners

Katheryn Soto

N/A

Proc # 3

Liquid-liquid Extraction
Materials

Vivarin Na2CO3
Solution

24 mL
Dichloromethane

Equipment

Graduated
cylinder

1 150mL
Beaker

Glass
funnel

Clay
triangle

Iron ring

Ring stand

125mL
separatory funnel
and stopper

Desc:

Pack the walls of a small glass funnel

with a small amount of glass wool.

Assemble sepratory funnel apparatus.

Decant sample solution into the sepratory

funnel.

Remove the glass funnel.

Seal the sepratory funnel with the glass

stopper.

Cool solution to room temperature.

In a graduated cylinder measure 8 mL

of Dichloromethane.

Add to mixture in sepratory funnel.

Stopper, invert and swirl the sepratory

funnel gently for 10-15 seconds.

With the funnel inverted, open the

stopcock to release any built up pressure.

Close stopcock.

Repeat swirling, inverting, and venting 3

times.

Replace separatory funnel in ring stand.

Allow to settle.

Drawer No.

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Results
Observations:

Layers of separation within the solution

became apparent as the solution settled and
cooled.

Upon the addition dichloromethane and

gentle agitation, a colorless layer of liquid (the
dichloromethane/organic layer) accumulated at
the base of the sepearatory funnel and a cloudy,
yellowish layer containing white sediments
(insoluble aqueous layer) accumulated above it.

Experiment:

Date:

Extraction of Caffeine

10/27/15

Name

Partners

Katheryn Soto

N/A

In a clean, dry 150mL beaker, collect the

clear (organic) layer of fluid by opening the
stopcock

Repeat extraction 2 times with 2 more 8

mL portions of Dichloromethane.
Equation Setup:

Drawer No.

Course / Section

#21

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Experiment:

Date:

Extraction of Caffeine

10/27/15

Name

Partners

Katheryn Soto

Proc # 4

Drawer No.

Course / Section

N/A

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Drying - Anhydrous Sodium Sulfate

Results

Materials

Equipment

Extracted

50mL
Dichloromethane
beaker
solution

150mL

Anhydrous
beaker
Sodium Sufate
Desc:

Add Anhydrous Sodium Sulfate to

extracted sample solution.

Stir and allow to settle

In a clean/dry 50mL beaker, slowly

decant the solution, allowing the crystals of
Anhydrous sodium sulfate to remain at the
bottom of the first container.

Rinse 150mL beaker with a small amount

of Dichloromethane to transfer remaining
sediment to the 50mL beaker.
Equation Setup:

Observations:

The crystals of Anhydrous Sodium Sulfate

were large, white, and insoluble in the solution.

Experiment:

Date:

Extraction of Caffeine

10/27/15

Name

Partners

Katheryn Soto

N/A

Proc # 6

Evaporation

Extracted and
dried Dichloromethane
solution

Course / Section

#21

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Results

Materials

Drawer No.

Equipment

50mL
beaker

Hotplate
Hood

Desc:

Heat solution on a hotplate (setting 3)

under the hood until dry.
Equation Setup:

Observation:

Solution was gently heated and allowed

to boil for 10 minutes, stirring occasionally.

Final product of evaporation was white

and cratered in appearance.

Experiment:

Date:

Extraction of Caffeine

10/27/15

Name

Partners

Katheryn Soto

N/A

Proc # 7

Recrystallization
Materials

Drawer No.

Course / Section

#21

CHEM
315/204

Results
Equipment

Dried sample

Hotplate
12-15mL Cold

Plastic
Acetone
pipet

Ice bath

Beaker

Petroleum ether
Desc:

Add 12-15mL Cold Acetone to dried

sample.

Heat solution on hotplate.

Add acetone in 2mL increments (20mL

maximum) as needed to dissolve completely.

Remove from hotplate and cool slightly.

Add petroleum ether dropwise, swirling

the mixture until the solution has a cloudy
appearance.

Cool in ice bath to assist crystal

formation.
Equation Setup:

Observations:

More than 15mL of cold acetone was

necessary to fully dissolve the dried sample
(30mL).

Solution went from clear to cloudy upon

the addition of petroleum ether.

Additional heating was necessary to

evaporate excess acetone from the sample.

An ice bath for a few minutes to aid

crystal formation.

Experiment:

Date:

Extraction of Caffeine

10/27/15

Name

Partners

Katheryn Soto

N/A

Proc # 8

Vacuum Filtration
Materials

Filter paper
20mL
Petroleum ether (cold)

Acetone (cold)

Caffiene
solution

Drawer No.

Course / Section

#21

CHEM
315/204

Results
Equipment

125 mL
Erlenmeyer flask

1 Buchner
funnel

1 Filter
flask

Rubber
tubing

Vacuum

Ring stand
and clamp

Dropper

Spatula

Desc:

Assemble the filtration apparatus (see

diagram on right).

Place the filter paper in the Buckner

funnel and moisten with a few drops of cold
petroleum ether.

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 solvent to the crystals

to remove any remaining impurities.

Wash crystals 3 times using the cold

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

Use a spatula to transfer the purified

crystals to a pre weighed vial.

Experiment:

Date:

Extraction of Caffeine

10/27/15

Name

Partners

Katheryn Soto

N/A

Drawer No.

Course / Section

#21

CHEM
315/204

Equation Setup:

Proc # 6

Drying Air Dry

Materials

Results
Equipment

Extracted and
dried Dichloromethane
solution in vial
Desc:

Leave the lid to the vial slightly ajar to

allow air to enter.

Air dry sample for one week in

instructors drawer
Equation Setup:

Experiment:

Date:

Extraction of Caffeine

10/27/15

Name

Partners

Katheryn Soto

N/A

Proc # 9

Mass Pure Sample

Materials

Drawer No.

Course / Section

#21

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Results
Equipment

Mass Pure Sample

Dry purified

Electronic
Mass weigh boat
2.736g
caffeine sample in
balance (0.001)
Mass boat + sample 3.116g
weigh boat

Calculator
Mass sample
3.116 2.736 =
0.380g
Desc:

Tare the balance

Observations:

Final product had a loose texture/did not

Pre weigh a clean dry weigh boat. Record

clump, was dull, white and had a fibrous
the mass.
appearance.

Weigh the sample. Record mass to three

decimal places.

Subtract the previously determined mass

of the empty weigh boat from the mass
measurement to determine the mass of the
purified caffeine sample.

Record all mass measurements to the

precision limit of the balance (0.001).
Equation Setup:
Mass of weigh boat and sample (g) mass of empty
weigh boat = mass of purified sample (g)

Experiment:

Date:

Extraction of Caffeine

10/27/15

Name

Partners

Katheryn Soto

N/A

Proc # 10

Percent Recovery

Drawer No.

Course / Section

#21

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315/204

Results

Materials

Equipment

Calculator

Desc:

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:

Percent Recovery
% recovery = (0.380/0.400) x 100

95%

Experiment:

Date:

Extraction of Caffeine

10/27/15

Name

Partners

Katheryn Soto

N/A

Proc #11

Course / Section

#21

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315/204

Melting Point

Results

Materials

Drawer No.

Purified caffeine
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 caffeine 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 Caffeine

Avg(oC):

1st M.P.
(oC)
233
234
233.5

2nd M.P. (oC)

236
237
236.5

235

Experiment:

Date:

Extraction of Caffeine

10/27/15

Name

Partners

Katheryn Soto

N/A

Drawer No.

Course / Section

#21

CHEM
315/204

Summary of Results:
The mass of the Vivarin tablets was 0.895g. The percent caffeine per pill was 44.7%. The mass of the
purified caffeine sample was 0.380g. The percent recovery for the extraction was 95%. The average
melting point of the purified caffeine sample was 235oC.

Analysis & Conclusions:

A polar molecule with a significant hydrophobic portion, the oxygen and nitrogen atoms within the
caffeine molecules structure are strongly electronegative, and draw electrons in their covalent bonds with
carbon towards themselves. This unequal sharing of electrons results in an uneven distribution of
electronegative charge within the molecule, or polarity, where carbon carries a slightly more positive
charge and nitrogen and oxygen carry a slightly more negative charge.
When combined with water, this polar molecule is easily dissolved via the formation of hydrogen bonds
with free electron pairs on the nitrogen and oxygen atoms, and is thus water soluble. When combined with
a nonpolar solvent like Dichloromethane, the hydrophobic segments of the Caffeine molecule interact with
the Dichloromethane. The increased solubility of caffeine in Dichloromethane by comparison to that in
water facilitated the extraction and isolation of the caffeine from water insoluble constituents of the tablet.
When combined with an aqueous solution of caffeine in a separatory funnel and gently agitated, the
caffeine separated into the organic dichloromethane (clear) layer. Because Dichloromethane is denser than
water, this layer sank to the base of the flask. 3 total additions of Dichloromethane were used to extract as
much caffeine as possible from the solution.
A small amount of Anhydrous sodium sulfate was added to remove excess water from the extracted
solution. Anhydrous compounds attract and form strong bonds with water molecules, aiding in their
removal. Any Dichloromethane that remained in the solution was then evaporated by gently heating the
sample on a hot plate.
As a final means of purification, acetone and petroleum ether were used to recrystallize the isolated
caffeine. These solvents are ideal for the recrystallization of this compound, as caffeine is only soluble in
them at elevated temperatures. A minimal volume of solvent was added to the crystals, and the solution

Experiment:

Date:

Extraction of Caffeine

10/27/15

Name

Partners

Katheryn Soto

N/A

Drawer No.

Course / Section

#21

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was gently heated until homogenous. Vacuum filtration was then used to harvest the crystals from the
mother liquor, and the sample was transferred to a weigh boat and allowed to air dry for one week.
A week later, the purified sample was weighed using an electronic balance to assess the final mass (0.380g).
This indicates theoretically that 95% of the total caffeine in the 2 Vivarin tablets (0.400g) was recovered in
the extraction and only 0.020g was lost.
To verify the identity of the compound and assess its purity, the melting point was determined using the
MelTemp device. The average melting point recorded (235oC) was within 3 degrees of the literature value
(236.1oC) indicating that the compound extracted is relatively free of impurities.
A potential source of error in this experiment is swirling the solution too vigorously in the sepratory flask
during each extraction. This can cause an emulsion to form, making isolation of the desired material from
the solution more difficult and in turn, the resulting compound less pure.

Experiment:

Date:

Extraction of Caffeine

10/27/15

Name

Partners

Katheryn Soto

N/A

Drawer No.

Course / Section

#21

CHEM
315/204

Literature Summary (Unknowns, Synthesized Compounds)

Unknown No.
CAS No.

Name (IUPAC)

58-08-2
3,7-Dihydro-1,3,7trimethyl1H-purine-2,6dione
Caffeine

Synonyms

Melting Point
(oC)

Lit 236.1oC
Exp 235.0 oC

Lit
Exp

Lit
Exp

Lit
Exp

Boiling Point
(oC)

Lit 178 C
Exp

Lit
Exp

Lit
Exp

Lit
Exp

Lit
Exp

Lit
Exp

Lit
Exp

Solubility
(Rel to Water)

Lit 2 g/100 mL @
R.T. / 66 g/100 mL
@ boil
Exp

Lit
Exp

Lit
Exp

Lit
Exp

Density
Rel to Water

Lit 1.23 g/cm3 at

20 C
Exp

Lit
Exp

Lit
Exp

Lit
Exp

Refractive Index Lit 1.679

(nD20)
Exp

Molecular
Formula

C8H10N4O2

Experiment:

Date:

Extraction of Caffeine

10/27/15

Name

Partners

Katheryn Soto

N/A

Structural
Formula

Drawer No.

Course / Section

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