National Autonomous University

from Mexico.
School of Higher Studies
Zaragoza.

Practice number 4:

Purification and identification of caffeine

starting from a commercial product (volt).

Members:
Morales Sánchez Paola.
Urbina Del angel Ivonne.

Advisor.
Iker Said Escalona Torres.

Group:
1353.

Delivery date.
17 de noviembre de 2018.
Summary.
To extract caffeine from the energy drink Volt, it was necessary
remove all the gas, so we don't have to wait days for it to completely go away
we support from a heating grill and a magnetic stirrer, thus a process
what was scheduled for three days could be completed in just 30 minutes. Following this, he was
they added the drops (mL) of ammonium hydroxide to change it from an acidic pH
to a basic one. Once having the basic pH and with the solution at a temperature
cold environment, extractions were carried out with the help of a funnel.
separation and methylene chloride. The obtained organic phase was taken to a rotary evaporator.
where the solidification of caffeine was observed in the round-bottom flask which
subjected to a high and constant temperature with a fisher burner to bring to
the sublimation in a cold finger. After this process, the caffeine was scraped off.
obtained from the cold finger, the obtained milligrams were calculated and were subjected to
tests in which identity and purity would be verified.

Introduction.
Caffeine is a naturally occurring component in coffee, tea,
chocolate, etc. caffeine consumption has stimulating effects on the system
nervous and our state of alertness. It also improves resistance to fatigue.
since it acts as a vasodilator on the heart. Its effects on the
The effects of the organism are: insomnia, anxiety attacks, tremors, and it also causes addiction.
Caffeine is an alkaloid of the methylxanthine family, whose metabolites include the
theophylline and theobromine compounds, with similar chemical structure and similar effects
(although of lesser intensity at the same doses). Its chemical formula is
C8H10N4O2, su name systematic it 1,3,7-trimethylxanthine o
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione. In pure form it is a white powder.
very bitter, this means that it is a natural product that contains nitrogen and
which presents basic (or alkaline) properties. They are stimulants that excite
to the central nervous system and the skeletal muscles, clearing the mind and
decreases the sensation of sleep.
Extraction is a process by which we can isolate a substance or groups of
substances based on the difference in solubility of them in a
determined solvent. The extraction can be carried out from solid mixtures or
of solutions of the desired substance in a given solvent. In both cases it must
observarse la formación de dos fases para que el proceso pueda realizarse: en el
first case a solid phase and a liquid phase, while in the second case must
to present two immiscible liquid phases. If there are two immiscible liquids
interacting to form two liquid phases and a third substance is added, said
substance will distribute between the two phases in a defined manner depending on
its affinity for different solvents. This equilibrium is independent of the
amount in which that substance is added.
Objective.
Extract caffeine from the energy drink Volt.
Purify caffeine by sublimation.
Identify caffeine through physical and chemical tests.
Hypothesis.
Extraction is the technique used to separate an organic product from a
reaction mixture or to isolate it from its natural sources. Sublimation, which is
the process where a solid transitions to the gaseous phase without passing through a liquid can be
used for purification process. Therefore, if an energy drink is subjected to
a process in which the caffeine it contains can be extracted, to
subsequently purify it through the sublimation process, performing the calculations
It will be possible to know the amount of caffeine extracted from the drink.
energetic.

Variables.
Independent.
Purity of the extracted caffeine.
Dependent.
Caffeine performance.

Experimental part.
Material.
A 1 L beaker.
A flat-bottomed round flask of 250 mL.
Universal support.
Fisher lighter.
Metal ring.
Three-finger tweezers.
1 L separation funnel.
150 mL beaker.
Test tube.
Test tube tongs.
Cold finger.
pH strips.
Capillary tubes.
Clock glass.
Magnetic stirrer.
Short neck funnel.

Team.
Rotavapor.
Analytical balance.
 Heating and stirring grill.
Vacuum pump.
Recirculator.

Reagents.
Ammonium hydroxide.
Methylene chloride.
Citric acid.
Sodium sulfate.

The gas was removed from the energy drink (volt) by heating a
a little while he stirred, to do it quickly.

He took the grill to the extractor hood without gas, where

without stopping the stirring, 4 mL of hydroxide was added
ammonia, to convert its initial acidic pH to a basic pH, without exceeding
of 10.

Once with basic pH and at room temperature or

cold, the solution was taken to a separating funnel in
where, with methylene chloride, 3 extractions were made
15 mL each, separating the organic phase from the
drink after each extraction.
In case there are in the extracted organic phase,
bubbles, it would dry with a sulfate spatula tip
of sodium which would be filtered with the help of a short funnel and
a little cotton as a filter, which was not necessary.
The organic phase obtained from the extractions was placed in a round-bottom flask, which
subsequently it was taken to a rotary evaporator, so that it could evaporate the solvent and in the
The flask will only contain the caffeine extracted from the drink.

With the round-bottom flask and caffeine without solvent, one

carried out a sublimation, which consisted of
put the flask to heat with the help of a
Fisher lighter, for the solid caffeine adhered
this would turn into a gas (without going through the
liquid), which when it comes into contact with the cold finger
inside the flask would stick to the finger due to
the change in temperatures. That is why it was important
that the water temperature inside the recirculator
it was cold, in addition to that it was constantly
I was maneuvering the flask so that all the caffeine
it was sublimated watching that at no time
turned into liquid, since if so, it
I would have to repeat the process. When the flask
the ball became completely transparent, it
it stopped the warming to take out the cold finger and
extract the caffeine obtained from it.

Registered the data of the caffeine weight obtained from the drink.
Volt energy, identity and purity tests were conducted.
 Murexide test.
It consisted of adding less than the tip of a spatula of
caffeine to a test tube to which 1 mL was added
citric acid, was taken to the extraction bell and with the
Fisher lighter heated until the acid evaporated,
Once the flask dried, a drop of was added.
ammonia, this would have to turn a color
red-purple.

Melting point test.

A capillary tube was taken, which was sealed on one side with
heat help to add a small sample of
caffeine, once the caffeine was introduced, the side was sealed
opposite, in order to prevent this from sublimating. The capillary tube
an electrothermal was taken where the point was measured
melting point.
Results.
Weight of the watch glass: 1.182 grams.
Weight of the glass of clock + caffeine: 1.264 grams.
Caffeine obtained from 473 mL of Volt drink: 0.082 grams.

If there are 0.054 grams in 360 mL of Volt.

360 mL - 0.054
473 mL - X

X = 0.07095 grams in theoretical calculation.

Percentage of error.

No photograph of the obtained caffeine is attached, as it was not found in the

phone.

Theoretical melting point of caffeine: 238°C

Experimental melting point within the electrothermal:
221°C.

Theoretically expected color in the test of the

murexida: Red or purple.
Color obtained in the experimental part: Purple.
Analysis of results.
Although the melting point of caffeine is theoretically, as already mentioned,
238°C, due to the pressure in CDMX, 30°C were subtracted so that in that range the
cafeína dentro del tubo capilar y este en el electrothermal, llegase a su fusión. Al
to obtain an intermediate result, it can be determined that caffeine, although yes in
its majority, it was not completely pure, due to some error made by the
students during the course of the practice and demonstrated in the error percentage.
In other words, the identity of the obtained caffeine was demonstrated
satisfactorily, since in the murexide test the color was as expected, a
purple tone that stated that the obtained substance was the expected one.

Conclusion.
Although the error percentage was very low, there were failures that did not prevent it from
will achieve the obtaining of completely pure caffeine. In the course of the
the practice stopped caffeine for a long period of time due to the bridge with
a famous reason for the faithful departed, which could have caused certain impurities
inside the drawer they adhered to it, which although it was covered, could have been
one option. Likewise, the mistake made could have occurred in the different
stages such as extraction or even sublimation.
Yes, the caffeine was not completely pure and the technique in the laboratory still has to
improve but, the result was very good and as expected, thanks to the tests,
it can be said that for the most part it was pure.
Likewise, it could be seen how acidic and thus how harmful it is to consume
this type of drinks.

Bibliography.
● Sánchez, A (2011,5, enero).Extracción de cafeína. [Web log post]
Recovered of
[Link]
L.G. Wade, JR. Organic Chemistry. Fifth Edition. Pearson Education.
Madrid, Spain. 2004.
● Soubeiran, Eugene (2008). Nuevo tratado de farmacia teórica y práctica.
Spain. J. Boet Printing Editorial.
● Pavia, D., Lampman, G. M., Kriz, Jr. G. S., Introduction to Organic Laboratory
Techniques: A Microscale Approach, Thomson Brooks, California, 2007
Mohring, J. R., Neckers, D. C., Laboratory Experiments in Organic Chemistry,
[Link] Nostrand Company, Inc., New York, 1973.
Caffeine questionnaire.
1 Through alkaline fusion, besides nitrogen, what elements can be...
identified? Write down all the reactions that take place with each one of them.
the elements.
Through the alkali fusion test, the presence of can be determined.
nitrogen, sulfur, and the halogens.

2. What is the reason for adding calcium carbonate during the reflux of the leaves?
of black tea?
To eliminate the tannins, mainly gallic acid, and promote the saline effect.
3. An aqueous solution containing caffeine must be extracted in the most
complete possible with 30 ml of chloroform. Would you use all the chloroform in one?
extraction or would you perform three extractions of 10 ml? Explain your choice based on
of the distribution coefficient
It is advisable to make three extractions with a volume of 10ml each, as
In that way, there would be less caffeine in the aqueous phase.
4. What problems can arise when trying to filter a pressurized ethereal solution?
reduced? What other techniques can be used?
Because ether has a low boiling point and using reduced pressure,
the boiling point will drop even further and it will happen that the solution decomposes, it will
freeze it or blow it up.
5. Is there any inconvenience in adding boiling stones to the hot liquid?
Yes, it is advisable to place the boiling bodies before heating the liquid.
to prevent the projection of the liquid.
6. In a vapor pressure versus temperature diagram, how would you explain it?
Does the liquid state not exist as an intermediate in sublimation?
Using the appropriate pressure and temperature, taking water as an example, we can
to change from a solid state to a gaseous state without passing through the liquid.
7. How could I determine the melting point of caffeine in the laboratory? What
Which variable(s) would you control?

A Thiele tube can be used for melting point and purity.

8. What causes the melting point of a substance to change when impurities are present?
does fusion get altered?
Since the vapor pressure changes due to the solute present, this will affect the
melting point.
9. In case you have a substance that can be purified by sublimation
And you don't want to use this method, which one would you choose, based on what?
If it is a solid, it could be purified through crystallization based on
its solubility and if it were a liquid it would be by distillation.
10. How can the melting points of benzene (5.5 ºC), dioxane be determined
(11.8 ºC) y orto benzoatode metilo (-12.4 ºC)?
Using a Thiele tube in a cold room where the temperature can be regulated.
11. The solubility of a compound "X" is: 100 g/ml in water and 450 g/ml in ether.
25 ºC. If the ether is used to extract compound 'X' from an aqueous solution and
the volume of ether and water are equal what is the distribution coefficient?

12. The following expressions are given:

12.1. For what type of extractions are equations 1 and 3 used?

For liquid-liquid extraction
12.2. According to equation 1, what physical interpretation do you give to the constant o?
distribution relationship in expressions 2 and 4?
Indicate where our solute of interest will be found, if equation 2 is a value.
large will be found in the organic phase, while if it is in equation 4 it
it will be found in the aqueous phase.
12.3. For the demonstration of equations 5 and 6, we start from equations 1.
Which ones would you start from, 1 or 3, to prove 5 and 6?
Be part of equation 3.
13. Suppose that 4 g of butyric acid contained in 500 ml of water is
they want to extract with 500 ml of ethyl ether and the KD = 3
13.1. Calculate the amount of butyric acid that is extracted if all the ether is used.
at once
3 grams of butyric acid are extracted.
13.2. How much butyric acid will be extracted if five successive extractions are made?
in portions of 100 ml?
3.5 grams of butyric acid will be extracted.
14. What minimum value of KD is necessary to extract 99.9% of a solute in
50 ml of aqueous solution with five successive extractions with 50 ml of ether?
A performance of 99.9% cannot be achieved.
15. If 5 successive extractions with portions of 100 ml of ethyl ether extract
nine tenths of the solute of an aqueous solution what fraction of the solute is
Will it extract with ten similar extractions if the KD = 10?
It would be a minimal fraction, as 90% has already been extracted and in the aqueous phase always.
there will be a little bit of solute left.