SFR3124

Experiment 1: Liquid-Liquid extraction of caffeine

Introduction:
Caffeine occurs naturally in tea leaves and coffee beans. Cocoa beans, used to
produce chocolate, contain a compound that is nearly identical in structure to caffeine.
Caffeine is also added to many types of soda and energy drinks. Caffeine is a white solid
material at room temperature. It is classified as an alkaloida nitrogen-containing basic (as
opposed to acidic) compound that is obtained from plants and has physiological effects in
the body. Caffeine is a stimulant and mildly addictive. Withdrawal symptoms may include
headache and irritability. There is no conclusive evidence that caffeine causes cancer or
heart disease. However, animal studies suggest it may be a weak teratogen (an agent that
causes birth defects in an embryo or fetus), so pregnant women are advised to limit their
intake of caffeinated beverages.
Procedure:
1. CAUTION: It is best not to get dichloromethane on your skin. You may choose to wear
gloves during this experiment. Otherwise, wash thoroughly if you do get some on your
hands.
CAUTION: Gas will build up in the separatory funnel while you are shaking it, so you must
vent the funnel occasionally to prevent the stopper from popping out, causing a mess and
possibly getting dichloromethane on your skin.
Obtain a separatory funnel and close the stopcock. Set up a ring stand on your lab bench to
support the sep funnel. Place 75 mL of coffee into the sep funnel. Add 20 mL of
dichloromethane and place the stopper in the top of the sep funnel. Shake the funnel for 1-2
minutes following the instructions given during the prelab lecture. Place the funnel back in
the ring stand and allow the two layers of liquid to separatethis may take a few minutes.
The lower layer will be dichloromethane. There may be an emulsion at the boundary
between the two layersan emulsion is a region where bubbles of one liquid are
suspended in the other liquid, and the two refuse to separate. If an emulsion occurs, use a
glass stirring rod to poke around in the emulsion to break it up. Ask the instructor for help if
the emulsion seems particularly stubborn.
Be sure the stopper is removed from the top of the sep funnel for the following drainage
stepotherwise the liquid will drain out of the funnel extremely slowly. Once the two layers
have separated, or are nearly separated, drain the lower dichloromethane layer into a clean,
DRY 250 mL flask. Be careful not to drain any of the COFFEE into the flask! It is best to
leave a very small amount of dichloromethane at the bottom of the sep funnel so as not to
accidently allow some coffee to escape.
The dichloromethane you just drained contains dissolved caffeine that has been extracted
from the coffee. However, it isnt possible to extract all the caffeine with a single portion of
dichloromethane. Therefore, you will do two more extractions using fresh portions of
dichloromethane in order to extract the majority of the caffeine that is in the coffee.

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2. Set the flask containing the first portion of dichloromethane aside. Add a fresh 20 mL
portion of dichloromethane to the coffee in the sep funnel. Shake the funnel for 1-2 minutes.
Allow the two layers to separate again. Then drain the lower dichloromethane layer into the
250 mL flask that already contains the first portion of dichloromethanebe sure to leave a
very small amount of dichloromethane in the funnel and dont allow any coffee to
drain out! At this point the two portions of dichloromethane are together in the flask.
3. Repeat step 2. At the end of this step, the flask will contain all three portions of
dichloromethane. If everything went well, most of the caffeine from the coffee should be
dissolved in this solvent.
4. The dichloromethane in the flask is certain to contain small amounts of water from the
coffee, even if you cant actually see visible water droplets. Therefore, it must be dried to
remove any water. If there are some visible droplets of water/coffee present, decant the
dichloromethane into a new dry flask, attempting to leave the water droplets behind when
decanting. If no visible droplets of water are present, skip the decanting step.
When there are no visible water droplets remaining, weigh out approximately 2 grams of
anhydrous sodium sulfate and add it to the dichloromethane (it is not necessary to obtain
exactly 2 grams). Swirl the container; then let it sit undisturbed for about 10 minutes. The
sodium sulfate will absorb any water (which you cant see) that is present. While waiting,
proceed to step 5.
5. Weigh a clean, dry 125 mL flask and record the exact mass on the report sheet. Obtain a
condenser, two rubber hoses, and a still head (a bent glass tube with a rubber stopper at
each end) for carrying out distillation. Attach the rubber tubes to the water outlets on the
condenser. Fill a 600 mL beaker about 1/3 full with distilled/purified water and place it on a
hot plate. Do not turn the hot plate on yet.
After the dichloromethane has dried for ~10 minutes, decant the dichloromethane into this
flask, being careful to leave all the sodium sulfate behind. You no longer need the sodium
sulfate, so it can be washed down the drain.
6. Assemble a distillation apparatus as follows. Place the flask containing the
dichloromethane into the beaker of water on the hotplate, so that the dichloromethane is
entirely submerged in water. Use a clamp from the cabinet under your lab bench to clamp
the neck of the flask so that it stays in place at the proper level. Place one stopper of the still
head into the mouth of the flask. Attach the condenser to the rubber stopper on the other
end of the still head. Place a waste beaker under the open end of the condenser to catch
liquid that will drop out during the distillation. If necessary, use another clamp to hold the
condenser in place.
One rubber hose should already be connected to each of the water outlets of the
condenser. Attach the other end of the lower rubber hose (the hose furthest from the still
head) to the white plastic tube coming out of the water faucet on your lab station. You may
have to first remove the black rubber attachment from the end of the white plastic tube.
Place the end of the upper rubber hose (the hose nearest to the still head) into the sink so
that water coming from the hose can drain into the sink. Ask the instructor to check your
distillation apparatus before proceeding.

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When you are sure the rubber hoses are attached correctly and tightly, turn on the water
faucet slowly and allow water to flow into the hoses and condenser. Adjust the water flow so
that it is not too fast (otherwise one of the hoses might blow off). Turn the hotplate on high.
The water in the beaker will begin to boil and its heat will cause the dichloromethane inside
the flask to boil. At that point, you will soon see dichloromethane begin to drip out of the
condenser into the waste beaker.
7. As the dichloromethane becomes hot and vaporizes (boils), the dichloromethane vapor
will travel into the cool condenser where it will condense back to liquid and drip out of the
bottom of the condenser into the waste beaker. The caffeine should not vaporize and travel
with the dichloromethane. Rather, it should be left behind in the flask.
Once all the dichloromethane has boiled out of the flask and the flask is dry, turn off the heat
and disassemble the apparatus. There should be caffeine residue inside the flask.
Record the appearance of the caffeine on the report sheet. Wipe the outside of the flask
completely dry and weigh the flask containing the caffeine. Record the total mass on the
report sheet, and then calculate the mass of caffeine extracted by subtracting the mass of
the empty flask. Complete the lab report by calculating your percent recovery of caffeine.
8. Pour the distilled dichloromethane into the bottle labeled recycled dichloromethane. The
coffee in the sep funnel can be discarded down the drain. Wash the sep funnel with water,
rinse it with acetone from the bottles with red lids near the sink, and return the funnel. The
caffeine can be washed out of the flask using water (and acetone if necessary). Return the
125 mL flask (do not put it in your drawer).
Data
1. Mass of empty flask ___________ g
2. Description of extracted caffeine: Include physical state (solid, liquid, gas) and color.
3. Mass of flask containing caffeine ___________ g
Calculations and Conclusions
4. Mass of caffeine extracted ___________ g = ___________ mg
5. Actual amount of caffeine in coffee sample ___________ mg
The coffee was prepared by the stockroom manager. According to the recipe used, the
coffee had a caffeine concentration of 1 mg/mL. Calculate the actual amount of caffeine in
the coffee sample you used for the extraction. Show work here:
6. Percent recovery of caffeine in coffee sample ___________ %
This is the percent of caffeine you were able to extract from the actual amount of caffeine in
the coffee sample. Pay careful attention to units!! Show work here: