PRCTICA 3

Aislamiento de cido acetilsaliclico del AlkaSeltzer y Otros

ingredientes activos de analgsicos comerciales.

1.- OBJETIVO GENERAL: Extraer y aislar de una muestra comercial de aspirina, el cido acetilsaliclico,
determinar su punto de fusin y comprobar el porcentaje (en peso) del cido extrado de la pastilla
comercial de acuerdo a lo reportado por el fabricante. Comparar los puntos de fusin del producto
sintetizado con el producto extrado.



MATERIALES:
vasos de precipitados de 50 mL.
gotero o una pipeta de plstico
cilindro de 10 mL
embudo
soporte universal
pinza de tres dedos
agitador de vidrio
papel filtro

REACTIVOS:

pastillas de algn medicamento efervescente que contenga aspirina y
bicarbonato de sodio (por ejemplo: Alka Seltzer)
cido clorhdrico (HCl) 6M (se puede utilizar la presentacin industrial,
que se conoce como cido muritico).
Agua (H
2
O)

PROCEDIMIENTO:

1. En un vaso de precipitados de 50 mL coloca la pastilla del medicamento elegido y
10 mL de agua. Espera a que termine de reaccionar. Puede quedar algo de slido sin
disolver.

2. Vierte en otro vaso de precipitados de 50 mL aproximadamente 10 mL de cido
clorhdrico y adicinalo a la solucin del medicamento, en porciones de 5 gotas,
utilizando el gotero o la pipeta de plstico. Al principio el slido insoluble que se
encontraba en el fondo del vaso se disuelve, con desprendimiento de burbujas de
CO
2
, ya que se trata de bicarbonato de sodio.

3. Una vez que se termine el bicarbonato, la aspirina que se encuentra disuelta en la
forma de su sal de sodio, acetisalicilato de sodio (CH
3
COOC
6
H
4
COONa), reaccionar
con el cido clorhdrico para formar el cido acetilsaliclico que es insoluble en agua,
por lo que precipitar:

CH
3
COOC
6
H
4
COONa + HCl CH
3
COOC
6
H
4
COOH + NaCl

4. Agrega cido clorhdrico hasta que ya no se forme ms slido.

5. Filtra la suspensin que tienes en el vaso, y enjuaga el slido (aspirina) que queda
en el papel filtro con dos porciones de dos mililitros de agua helada.

Comentario [J1]: Se puede colocar la
solucin en bao de hielo para favorecer la
precipitacin mientras se adiciona el HCl
Comentario [J2]: Se sugiere
estandarizar la prctica para establecer un
rango de volumen de HCl que garantice la
formacin de la mayor cantidad de
precipitado
6. Secar la muestra muy bien. Determine el peso y el punto de fusin.

7. Calcule el % de cido acetilsaliclico presente en la muestra comercial, y comprelo
con los valores reportados por el fabricante en el empaque.

8. Lava el material que utilizaste.
9. Guardar la muestra para su comparacin por TLC con la aspirina a sintestizar en
la prctica 4
Bibliografa

UNIVERSIDAD AUTNOMA DE AGUASCALIENTES. CENTRO DE BACHILLERATO Y SECUNDARIA.
DEPARTAMENTO DE QUMICA. LABORATORIO DE QUMICA. MANUAL DE PRACTICAS DE
LABORATORIO DE QUMICA A MICROESCALA PARA LA MATERIA DE QUMICA II DEL QUINTO
SEMESTRE DE BACHILLERATO.

UAA, Centro de Bach. y Sec., Departamento de Qumica, Ing. Jorge H. Ramrez Alonso, Julio 2006
IDENTIFICATION OF ACTIVE INGREDIENTS IN ANALGESIC DRUGS
The structures of the three active ingredients from common pain pills are shown below.
STRUCTURE



ACTIVE
INGREDIENT
Acetylsalicyclic
acid
Acetaminophen Ibuprofen
Purpose of the experiment: For this lab, you will be introduced to a technique called
thin layer chromatography (TLC). This technique can be used to identify all the
components in a mixture. In this experiment, you will use this technique to identify
analgesic drugs by isolating the active ingredients from these drugs. You will work in
groups of three, and each member of the group will isolate the active ingredient in one
of the three drugs. You will then share your sample with other members of the group.

Procedure:
1. Isolation of active Ingredient
Choose one of the three unknown tablets. Record the exact weight of the tablet before
proceeding. Crush the tablet between a folded piece of weighing paper. Place the
powder in a 3 mL conical vial, add about 2 mL of methanol, cap the vial and shake
vigorously. Allow the solution to sit and settle for a few minutes. Transfer the cloudy
solution (supernatant) to a 16 x 125 mm test tube. Repeat the extraction process by
adding an additional 2 mL of methanol in the vial, and transfer the solution to the same
centrifuge tube that contains the first extract. Centrifuge the mixture for 2-3 minutes or
until the supernatant liquid is clear.
Prepare a 2 cm alumina column (or about 0.5g of alumina) using a Pasteur pipet and add
about 2 mL of methanol to wet the alumina. Allow the liquid to drain until the level of
methanol reaches the surface of the alumina. If necessary add more methanol but dont
let the column run dry (in other words dont let the methanol to drain below the surface
of the alumina). Carefully transfer the clear liquid from the test tube to the column
using the Pasteur pipet and collect the liquid that passes through the column in a small
beaker. Again wait for the liquid to reach the surface of the alumina, add an additional
1 mL of methanol and allow the solution to drain into the same beaker. This ensures
that the entire active ingredient in the analgesic drug has been eluted from the column.
At this point, keep a small amount of sample for TLC (see section 2).
For the rest of the sample, evaporate the solvent by placing the beaker in a warm sand
bath or a warm water bath at about 50-70C. When the solvent has completely
evaporated or until the remaining liquid is no longer evaporating remove the vial from
the water or sand bath and cool it down to RT. It is essential to complete the
evaporation within 10-15 minutes. Place the beaker in an ice-bath if necessary you can
scrape the inside of the beaker with a glass rod or spatula to induce crystallization.
If your crystals are wet after the evaporation filter the crystals using the Hirsch funnel
connected to a vacuum, break up the lumps and allow the solid to dry for 5 minutes on
the funnel. When the crystals are completely dry, determine the isolated weight.
Determine the melting point and calculate the % recovery.
2. Thin Layer Chromatography:
Obtain a TLC plate and a few micropipets from the reagents bench. Use a pencil and
lightly draw a line about 1 cm above the bottom of the plate. Mark the plate with six
points evenly spaced where the samples will be spotted, three knowns and three
unknowns. Obtain a few drops of the knowns in small test tubes.
Use a 250 mL beaker as a developing jar by introducing enough solvent to cover the
bottom of the jar to about 0.5 cm (about 10 mL). Introduce a filter paper folded to fit in
the jar, and cover the beaker with a watch glass. Allow the solvent to soak the filter
paper and let the atmosphere in the jar equilibrate. The sample can be applied on the
plate by gently spotting the tip of the filled capillary to the plate, and repeat the spotting
about 2-3 times depending on the concentration of the solution. Between each spotting,
allow the solvent to evaporate. The solvent used is 0.5% acetic acid in ethyl acetate.
Visualize the developed TLC plate under UV light and mark them with pencil. Place
the plate in the iodine chamber and mark the spot by indicating iodine active (IA).
Sketch the plate in your notebook with any necessary comments.
Calculate the Rf values and identify the three analgesic drugs. Confirm the identity of
your drug by recording an IR spectrum and comparing it with the authentic spectrum.
Label the important peaks in the IR spectrum that correspond to functional groups
present in the compound.
Questions:
1) Define R
f
value.
2) Which compound in each of the two pairs below will have a larger Rf value if they
were both run on the silica gel TLC plate in 5% ethyl acetate/hexane: benzene or
benzoic acid, dimethyl amine or cyclooctanone? Explain your reasoning.
3) If a 625 mg Tylenol tablet contains 81% acetaminophen how many moles of
acetaminophen are present in the tablet?
4) What will be the result of the following errors in TLC technique?
a) Solvent of too high polarity
b) Solvent pool in developing jar too deep
c) Forgetting to remove the TLC plate when the solvent has reached the top of the
plate
d) Forgetting to mark the solvent front immediately after the removal of the plate
from the developing chamber.
References:
1) Mayo, D. W.; Pike, R. M.; Trumper, P. K. Microscale Techniques for the
Organic Laboratory; Wiley & Sons: New York 2001.
2) Pavia, D. L.; Lampman, G. M.; Kriz, G. S.; Engel, R. G. Introduction to
Organic laboratory Techniques, A Microscale Approach; Saunders College
Publishing: Fort Worth 1999.
3) Padias, A. B. Organic Chemistry, Laboratory Manual; Hayden McNeil
Publishing: Plymouth 2001.
Loosen the cap a few times during the mixing process to release any build up of
pressure in the vial.
Dont forget to balance your centrifuge tube with another test tube of the same
volume. You can accomplish this by using another lab mates test tube or a test tube
that containing water.
With a second Pasteur pipet, insert a small piece of cotton or glass wool through the
top and wedge gently in the constriction of the pipet. Use a paper towel to cover the
narrow part of the pipet tip and break off the tip to a length of about 2 cm. Clamp the
pipet in a vertical position so that the liquid from the column drains into a small beaker.
Add alumina and tap the column with your finger to pack the alumina.
To speed up the evaporation, direct a gentle stream of air into the vial.
The volume of the solution should be less than 0.5 mL before you stop the evaporation
process. Ibuprofen has a low melting point so it might be melted during the
evaporation.
Aspirin will partially decompose if you heat it too long.
REVISAR:
TECNICAS DE EXTRACCION, PUNTO DE FUSION
ANALGESICOS COMERCIALES MAS COMUNES, SUS EXCIPIENTES, ETC. Y
SUS USOS.
SINTESIS DE LOS TRES ANALGESICOS DE ESTA PRACTICA
TRAER
TABLETAS DE ALKASELTZER
ACETAMINOFEN , IBUPROFENO
TIENEN QUE SER PASTILLAS BLANCAS SIN COLORANTES.
Envases de heces pequeos par guardar lo ingredientes activos