Experiment 6:

EXTRACTION of ANALGESICS

Objectives

To learn the technique of acid-base

extraction.
To separate aspirin from acetaminophen using
the extraction technique.
To learn the techniques of drying organic
solvents and vacuum filtration.
To analyze the purity of the aspirin and
acetaminophen samples using HPLC analysis.

Before coming to lab

Watch the following videos to help you

understand the techniques that will be
used.
Extraction

http://www.wonderhowto.com/how-to/video/how-to-do-a-liquid-liquidextraction-in-the-chemistry-lab-259811/view/

Vacuum

Filtration

http://video.google.com/videoplay?docid=4541453194468704643#docid=1104445520143750871

Drying

Organic Solvents

http://www.wonderhowto.com/how-to/video/how-to-dry-an-organic-solution-in-thechemistry-lab-259802/view/

ACTIVE INGREDIENTS
GOODYS POWDERS
O
H

O
H3C

O H

CH3

O
OH
Aspirin

Acetaminophen

2-Acetylsalicylic acid

4-acetamidophenol

MF: C9H8O4

MF: C8H9NO2

MW: 180.2 g/mol

MW: 151.2 g/mol

mp: 138-140 C

mp 169-172oC

Hazards: Toxic, Irritant

Hazards: Toxic, Irritant

pKa: ~3.5

pKa: ~10
o

Solubility in H2O: 1g in 300mL @ 21 C

500 mg/powder

Solubility in H2O:1g in 150 mL at 21oC

325 mg/powder

ACIDBASE EXTRACTION
CHEMICAL EQUATIONS
O

O
CH3

CH3

O
C
+
O, Na

O
C
+ Na+ , HCO3- (aq)
O H

H2CO3

Sodium carboxylate

Carboxylic acid

Organic insoluble,
water soluble

Organic soluble,
water insoluble

HCl(aq)

O
CH3

H2O + CO2(g)

O
C
O H

Carboxylic acid
Organic soluble,
water insoluble

O
H

CH3
+ Na+ , HCO3- (aq)

OH
Acetaminophen
Organic soluble,
water insoluble

NO REACTION
Acetaminophen remains
soluble in the organic phase and
insoluble in the aqueous phase

ACIDBASE EXTRACTION
FLOW CHART
2 Goody's Powders
25 mL Ethyl Acetate
25 mL sat. NaHCO3
Separatory
funnel

Organic layer
(acetaminophen)

aqueous layer
(aspirin salt)

re-extract with 10% NaHCO3

re-extract with ethyl acetate

Combined aqueous layers

(aspirin salt)
1. 6M HCl
2. Filter

aqueous filtrate = waste

Organic layer
(acetaminophen)
1. dry over
MgSO4
2. filter
3. evaporate

Aspirin

Acetaminophen

SEPARATORY FUNNEL TECHNIQUE

Be sure the
stopper is
tightly sealed
before
inverting!
Be sure the
stopcock is in
the horizontal
position
(closed)
before adding
any liquid!

Always keep
one finger on
the stopper!

SUCTION FILTRATION TECHNIQUE

Always

clamp the suction

flask to a ring stand!
Run the red vacuum hose
to the yellow vacuum line to
pull suction!
To vacuum
line

DRYING ORGANIC SOLVENTS

Add a small amount of
MgSO4 to the organic
solution and swirl.

If the MgSO4 continues to clump

and sink to the bottom, continue to
add.
If the MgSO4 settles out of
solution slowly (like a snow globe),
the solution is dry.

OVERVIEW

Perform acid/base
extraction using
separatory funnel.
ACETAMINOPHEN
(O)

Isolate ASPIRIN and

ACETAMINOPHEN in
separate flasks.

ASPIRIN SALT
(A)

OVERVIEW
ACETAMINOPHEN

Dry organic layer with MgSO4.

Suction filter to remove MgSO4 from liquid.

Evaporate liquid on hotplate.

Reweigh to obtain final weight & calculate % recovery.

Dissolve solid in REAGENT acetone.

Submit HPLC sample.

Transfer to large sample vial and submit to instructor

until next lab period.

OVERVIEW

ASPIRIN

Add acid to recover solid aspirin.

Suction filter to recover solid aspirin.

Submit HPLC sample.

Secure aspirin in large filter paper and submit to

instructor until next lab period.

NEXT LAB PERIOD

Obtain final weight of aspirin.

Calculate % recovery.

Prepare sample for melting point analysis.

THEORETICAL RECOVERY

For this experiment, we dissolved 2 Goodys

powders in 25 mL of ethyl acetate.
In each Goodys powder, there is 0.500 g
of aspirin and 0.325 g of acetaminophen.

Theoretical Recovery:

0.500 g per powder X 2 powders = ? g of Aspirin

0.325 g per powder X 2 powders = ? g of Acetaminophen

PERCENT RECOVERY

After the product has been dried sufficiently,

the ACTUAL YIELD can be determined.
In theory, you should be able to recover 100%
of each compound, however this is not always
the case.
In order to determine the success of your
recovery, the percent yield is calculated as
follows:

Percent recovery : actual recovery (g)

X 100
theoretical recovery (g)

Table 6.1

Theoretical recovery after extraction (g)

Actual recovery after extraction (g)
% Recovery after extraction

Aspirin

Acetaminophen

calculated

calculated

Obtain weight

Obtain weight
this lab!

next lab!
calculated

calculated

Table 6.2
HPLC retention times (min) and area %
Standards

Compound

Rt

(min)

Aspirin
Sample
Rt
area %

(min)

Acetaminophen
Sample
Rt
area %
(min)

Aspirin
Acetaminophen
Samples containing a single compound are considered PURE samples,
while those containing both compounds are considered MIXED (IMPURE)
samples.
Be sure to attach both sample chromatograms to final lab report!

SAFETY CONCERNS

Acetone and ethyl acetate are

extremely flammable! Wear safety
goggles at all times and use extreme
caution when heating!

Hydrochloric acid is corrosive!

WASTE MANAGEMENT

The drying agent (MgSO4) and filter

paper should be placed in the
container labeled MgSO4 Waste
provided in the hood.
Place all liquid waste in the container
labeled ACIDIC AQUEOUS
WASTE.

LABORATORY NOTEBOOK
(Pre-lab)
OBJECTIVE

(Must clearly state)

What is the goal of the experiment?

How will you accomplish this goal?
How will you determine if it worked?

TABLE OF PHYSICAL DATA

(Complete the following table using

MSDS sheets from a site on WWW Links ONLY. Wikipedia is unacceptable)
Compound
Acetone
Ethyl acetate
Hydrochloric acid
Sodium bicarbonate
Aspirin
Acetaminophen

MW (g/mol)

bp (Co)

mp (Co) d (g/mL)

HAZARDS

XXX
XXX
XXX
XXX
XXX
XXX

XXX
XXX
XXX

REFERENCE TO PROCEDURE

(Must include)

full title
Edition
authors
page numbers where actual procedure can be found

LABORATORY NOTEBOOK
(In-lab)
DATA/CALCULATIONS

EXTRACTION:

Theoretical recovery CALCULATION for aspirin (not just the value!)

Theoretical recovery CALCULATION for acetaminophen (not just the value!)

initial weight of 150 mL beaker

weight of 150 mL beaker+ acetaminophen

Weight of small filter paper

Weight of large filter paper

HPLC vial slot # for aspirin sample

HPLC vial slot # for acetaminophen sample

DRYING AND ACETAMINOPHEN RECOVERY:

ASPIRIN RECOVERY:
HPLC ANALYIS:

EXPERIMENTAL PROCEDURE

In paragraph form, briefly describe the procedure that you actually

followed during the lab.
Paragraph must be written in PAST TENSE, PASSIVE VOICE.

Include any volumes or weights of chemicals used during the experiment.

Include any mistakes, accidents, or observations if necessary.