Candice Randall

337 Laboratory, Section 017

Department of Chemistry
Portland State University

Experiment 5: Isolation of Caffeine from Tea Leaves

Abstract:
The purpose of this lab is to extract and sublime caffeine from prepared tea. Caffeine is isolated and
purified using a four step process which includes liquid/solid extraction (prepared tea), liquid/liquid
extraction, roto evaporation, and sublimation. The results of this experiment yielded a melting point of
218 oC, a recovered mass of 0.181g, and an IR graph of a purified sample of caffeine which shows CH3
bonds at ~2900 and 3100, C=O bond at ~1750, C=N bond at ~1600, C-N bond at ~1200, and C=C
bond at ~1450.

Introduction:
Caffeine is a natural alkaloid organic compound found in tea leaves, nuts, coffee, mate leaves, and
guarana paste. Alkaloid products are organic compounds with weak bases and they contain nitrogen
atoms. Caffeine and other alkaloids are imperative in physiological processes and are a main ingredient
in many pharmaceuticals for pain relievers, cardiac support, as well as respiratory, diuretic and
psychiatric stimulants. Caffeine characteristically has two fused rings that contain one or more non
carbon atoms, in this case nitrogen. It can be extracted and isolated following a sequence of techniques
which includes solid/liquid extraction, liquid/liquid extraction, roto evaporation, and sublimation. The
solid/liquid phase of the experiment consists of the tea leaves being steeped in water which allows the
will allow the caffeine to be extracted from the solid leaves. Next, using liquid/liquid extraction the
caffeine is separated from the water using dichloromethane (DCM). Likes dissolve likes and in this
case the DCM, an organic solvent, will allow the caffeine, an organic compound, to be dissolved and
isolated from the non-polar water that it was originally extracted in. After the liquid/liquid extraction is
completed, the DCM is removed from the from the liquid/liquid mixture using a separatory funnel and
sodium anhydrous is added to the mixture to remove any additional water that may have been removed
with the DCM. The roto evaporator is used to evaporate the DCM, leaving behind unpurified caffeine.
To remove any additional impurities, the dried caffeine is sublimed; the vapor is re-condensed back to
solid, and allowed to re-dry in a sublimation apparatus where purified caffeine is the final isolated
product. In this experiment, sublimation is a useful purifying technique because of caffeine’s
particularly high vapor pressure

Experiment:
Isolation of caffeine from prepared tea:
Materials and Instruments:
 50 ml of prepared tea
 1.0g sodium carbonate monohydrate
 15 ml plus 10ml of dichloromethane (DCM)
 Separatory funnel
 0.75 g sodium anhydrous
 Roto evaporator
 Sublimation apparatus as set up in Portland State Ochem laboratory Manual Experiment 5.
 Hot plate
50 ml of prepared tea and 1.0 gram of sodium carbonate monohydrate were added to a seperatory
funnel and allowed to react until the sodium carbonate dissolved. 15ml of DCM was added to the
funnel and allowed to react for 5 minutes, being careful to slowly release gas that is produced from the
reaction according to the directions in the Portland State Ochem Laboratory Manual for Experiment 5.
The cap was removed to allow the tea and DCM to separate then the DCM was drained into a cleaned
beaker and the process was repeated again using 10ml of DCM. Next, approximately 0.75 grams of
sodium anhydrous was added to the DCM to remove any additional water that may have escaped
through the separatory funnel. The DCM was transferred to a 50 ml round bottom flask and
evaporated using the roto evaporator. The roto evaporator was set up according to the TA’s
instructions and the guidelines in the lab manual appendix. Next, the unpurified dried caffeine was
transferred to the sublimation apparatus by dissolving it in approximately 1ml of DCM. The DCM was
evaporated using a hot plate. When the caffeine was dried, the 15ml centrifuge tube with ice was
placed in the adapter and onto the top of the 25ml flask. The vent was turned on and the sublimation
process proceeded. The sublimation guidelines are further detailed in the lab manual experiment 5.

Discussion and Results:

Figure 1. Molecular structure of caffeine (http://commons.wikimedia.org/wiki/File:Caffeine.svg)

Figure 2. Sublimation apparatus (http://www.geocities.ws/dcarrd2000/introduction1.html)

Table 1: Melting point and mass of isolated caffeine sample
Mass of caffeine recovered 0.181g
Melting Point of purified sample 218oC

When comparing the completed melting samples melting point of 218oC to pure caffeine’s melting
point of 238oC it is apparent that the sample has a depressed melting point. This indicates that the
sample is not as pure as a 100% pure sample of caffeine.

Figure 3. IR Spectra of Patrick’s purified caffeine sample

Table 2. Bonds present in Patrick’s purified sample of caffeine

Bonds CH3-N C=O C=N C-N C=C
Peaks ~2900 and ~1750 ~1600 ~1200 ~1450
cm^-1 3100

Figure 4. Expected IR spectrum of purified caffeine

Table 3. Bonds present in a 100% purified sample of caffeine
Bonds CH3-N C=O C=N C-N C=C
Peaks ~2900 ~1700 ~1660 ~1250 ~1650
cm^-1

When comparing figure 3, the sample IR spectra with figure 4, 100% purified caffeine, it is
apparent that the figure 3 does not support a 100% purified sample of caffeine. This is apparent
because of the differences in relative transmittance of the bonds observed in each of the two figures.
The purified sample from this experiment has slightly different bond locates. There are two CH3 bond
dips in the purified sample one at ~2900 and the other at ~3100. The dips are notably smaller than the
CH3 dip in figure 4. C=O, C=N, and C-N bonds are slightly off by less than 100 cm-1, however the
C=C bond is off by ~200 cm-1. These differences, as well as the additional dips noted between 500 and
1750 cm-1 are all indications that the purified sample from the completed experiment still has some
remaining impurities. The steps that should remove the impurities include the addition of sodium
anhydrous to the DCM mixture to remove any additional water and the sublimation, vaporization, and
recondensing of the roto evaporated sample. These steps may have not been completed with the most
accuracy and the standard equipment used may have also been a factor in the execution, accuracy, and
precision of the purification.
Unfortunately, my particular experiment was unsuccessful in completing the sublimation step
and consequently I did not sublime a purified sample of caffeine. I was able to complete the
liquid/liquid extraction and roto evaporation successfully as well as the initial evaporation of DCM
after being transferred to the sublimation apparatus. The error in my experiment occurred with the
accidental backing up of water from the venting tube during. This water back up occurred because of a
malfunction in the water suction at my particular work station. When the water vent was turned on, the
house connecting my flask to the vent was flaccid which implied that there was no suction coming
through the house. When Elias and myself attempted to fix the flaccidity of the hose, the water from
the vent backed up into the flask. I attempted several different techniques to save my sample which
included continuing the sublimation at a different station, re-evaporating the water using the roto
evaporator, and boiling the water and caffeine mixture on a hot plate to remove the additional water.
Unfortunately, none of these techniques worked in removing the excess water from the caffeine.
Conclusion:
The purpose of this experiment was to isolate caffeine from a sample of prepared tea leaves
using solid/liquid extraction, liquid/liquid extraction, roto evaporation, and sublimation. The isolation
and purification of caffeine has numerous uses within the pharmaceutical and medical industry and
therefore accurate purification and isolation of caffeine is an imperative chemical process. The results
of this experiment yielded a more purified sample than the starting product, but when compared to a
standardized and 100% purified sample of caffeine, the experimental sample had a melting point of
218oC which is 20oC lower than the standardized sample. Additionally, the IR spectra showed mild
differences in bond locations of CH3-N, C=O, C=C, C-N, and C=N along with additional peaks and
dips that indicate the relative impurities still abundant in the sample such as water and additional bond
interactions from the sodium anhydrous and calcium carbonate that were added during the experiment.
References:
Organic Chemistry Laboratory 1, CH 337M; Department of Chemistry, Portland State
University: Portland OR; Exp 5

Organic Chemistry Appendix, Department of Chemistry, Portland State University: Portland OR

http://commons.wikimedia.org/wiki/File:Caffeine.svg

http://webbook.nist.gov/cgi/cbook.cgi?ID=C58082&Units=SI&Mask=80#IR-Spec

Questions:
1. It depends what are the substances we are going to use. Not all substances can benefit purely from
one technique. Sublimation is when a solid chemical vaporizes into a gas which is them cooled back
into a solid which allows the impurities within the sample to be left behind because they have a lower
vapor pressure than the compound that is being isolated. Conversely, during recrystallization the
substance is dissolved in an appropriate solvent where it will then be filtered to remove solids and then
cooled to form crystals. The differences that need to be paid attention to are the vapor pressure,
melting point, boiling point, solubility, and partial pressure of the compound being isolated, but also of
the compound it is mixed with and the impurities that are present. Considering these factors will allow
one to make an educated decision as far as what process they should use for purification.

2. The atmospheric sublimation can be used only for solid with a relatively high vapor pressure.
In our compounds compound 1 with the highest vapor pressure of 790torr at its melting point is
subjected to sublimation at atmospheric temperature then compound 2 and lastly compound 3. Again,
it is important to remember that sublimation refers to the process of vaporizing a solid into a gas and
back into a solid which occurs when substance with a high vapor pressure is heated to the melting
point and allowed to recondense into a more purified solid. The impurities that are left in the flask are
not able to vaporize because of the lower vapor pressure and consequently do not reform a solid on the
cold finger of the sublimation apparatus.

3. That's because the caffeine ended up in the vacuum pump. The cold finger must always be kept cold
during procedure so it produce a surface at a very low temperature for the sublimed caffeine vapor to
condense back into the solid state and be ready for collection. If the cold finger warms up then the
caffeine vapor will just pass through it without condensing and will end up in the vacuum pump or
leaking through the sublimation apparatus into the atmosphere.