Goody's acid base AC
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Goody’s Acid-Base Powder Extraction
N
ame: Aliyah Carmichael
Chem 2123-002
Abstract
This acid-base experiment’s purpose was to extract 1400mg of Goody’s Tablets into four
components using solvents dichloromethane and ethanol and chemical properties to determine
aspirin and acetaminophen’s purity and percentage recovery.
The four ingredients are
aspirin, acetaminophen, caffeine, and a binder. These ingredients were isolated based on their
physical properties, such as solubility and density. The recovering results found were 2.84% &
200% for aspirin and acetaminophen, respectively.
Introduction
Goody’s Powder is an over-the-counter pain reliever that contains aspirin, acetaminophen,
caffeine, and a binder. A binder is a neutral substance that holds ingredients in a tablet
together after packing and shipage; the binder isn’t soluble in common organic solvents or
water.
The combination of aspirin, acetaminophen, and caffeine provide fast pain relief and
are all soluble. (figure 1)
Figure 1
The extraction process is when ingredients in a mixture are separated into pure components, which
can be through filtration, distillation, or chromatography. When it comes to the extraction in this
experiment of multiple substances that are smaller molecules, chemical reactivity and physical
properties such as solubility, polarity, and density are to be relied on. In this experiment, immiscible
(not able to be mixed) solvents are used for liquid-to-liquid extraction to extract compounds by
manipulating boiling points, breaking their intermolecular forces, resulting in a precipitate. A
separatory funnel is used for the separation process and drainage of the extracted compound. The
organic solvents used were dichloromethane and ethanol.
“Like dissolves like.” Solubility and density properties play a vital role in this acid-base reaction.
Figure 2 below provides an informative guide about the molecular weight and melting point of the
various components and their molecular structure that helps to identify whether they can act as an
acid or base compared to each other.
The pKa for aspirin is 3.49, and the pKa for acetaminophen is
9.71, proving that aspirin is more acidic than acetaminophen. While Aspirin
and caffeine were soluble in the dichloromethane. The binder and
acetaminophen were not, resulting in a crystal-like precipitate. Hot ethanol
was used to extract acetaminophen from the insoluble binder, and the
extraction process was repeated. Adding HCl to the aqueous base with
aspirin allowed aspirin to form an H-bonding interaction, causing aspirin to
reform into a solid.
Figure 3 displays the different compounds and their solubility in several
organic solvents. (Chloroform has similar atomicity and molecular shape as dichloromethane, with a
single chlorine atom difference) This experiment aimed to separate compounds using organic solvents
and the extraction technique to determine Asprin and acetaminophen percent recovery. It is
hypothesized to receive a 100% recovery of all ingredients.
Crystal like acetaminophen
and binder
Materials
Lab coats, safety goggles, and gloves were worn for safety.
1.
Goody’s Powder
2.
Dichloromethane
3.
Ethanol
4.
3M
N
aOH
5.
3m HCl
6.
Hot plate
7.
Watch glass
8.
Three beakers
9.
Sepatortory
10.
Funnel
11.
Filter paper
Figure 2
Figure 3
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12.
Separatory funnel & glass stopper
13.
Ring stand and iron ring
14.
pH paper
Experimental Procedure
1.
A 1400mg sample of Goody’s Powders was weighed to start the experiment.
2.
Goody’s powder sample was added to a small Erlenmeyer flask.
3.
8mL of dichloromethane was added to the flask and warmed on the hot plate at 95 degrees C. Watch
glass placed on top to prevent evaporation.
4.
Boiled Goody’s and dichloromethane until caffeine and aspirin dissolved and a precipitate of
acetaminophen and binder was formed.
5.
The remaining solution was transferred into a new beaker labeled #1 and set aside.
The precipitate
solid was then transferred to filter paper.
6.
The precipitate was added to another beaker of 6mL of ethanol and set to a low boil.
7.
After the boil, the hot solution was gravity-filtered through filter paper into a funnel and rinsed with
hot ethanol.
8.
The insoluble binder left was collected, cooled, and weighed.
9.
The hot solution with ethanol is cooled, set aside, evaporated off ethanol, and recrystallized with
H2O as acetaminophen. This sample was collected, dried, and weighed.
10.
Return to beaker #1.
11.
The dichloromethane solution from beaker #1 is transferred into the separatory funnel
12.
Added 2mL of 3M
N
aOH into the separatory funnel and placed a glass stopper on top.
13.
Held stopper in place, inverted the funnel and shook funnel by to mix layers.
14.
Allowed solvent vapors to
escape by opening and closing
the stopcock. ( Done
frequently)
15.
Returned funnel to ring stand
and placed in an iron ring.
16.
Allowed solution to settle and
removed glass stopper from funnel after two layers were clearly separated.
17.
Opened the stopcock and only allowed the bottom half to drain into a new beaker, labeling this as
beaker 2.
18.
The top layer was drained into a different beaker and labeled beaker 3.
19.
Beaker #2 was placed back into the funnel for a second extraction.
20.
Steps 12- 16 are repeated for the second extraction procedure with an additional 2mL of 3M
N
aOH.
21.
Drained Diclhoridemethane into new beaker #4.
22.
Drained top layer into beaker #3.
23.
The organic layer in beaker #4 was dried with Sodium sulfate and filtered into a smaller beaker.
24.
Allowed Dichloromethane to evaporate.
25.
Collected caffeine residue. Dried and weighed caffeine.
26.
Added 3M Hcl drops to beaker 3, stirred in between the drops added. Once pH was acidic, stop
adding Hcl 6 (Use of pH strips to check balance). For no more than 5 minutes, the solution is heated
for the solid to be dissolved.
27.
The solution was cooled to room temperature and placed into an ice bath; the solid collection was
Aspirin. This was then dried, collected, and weighed.
Results and calculations
Discussions
The calculations prove the experiment to be inconsistent with the hypothesis. Almost none of the
Aspirin was left, with a recovery of 2.84%, and Acetaminophen had a recovery of 200%. Caffeine
23.52% and binder 29.41%. The hypothesis was that 100% of the components would be extracted
from Goody’s powder.
Out of 1400 mg of Goody’s powder, the theoretical yield of aspirin,
acetaminophen, caffeine, and binder was 728, 364, 45.4, & 262.5, respectively. The actual yields
obtained were: 20.7, 730,10.7, 77.2, and 838.6, respectively.
Something went wrong Somewhere in the process; it may have been adding the wrong solvent, spilling
the solution, or allowing vaporation to happen while heating or overheating. Still, the numbers are off
and do not hold to the hypothesis of the extraction experiment.
N
ew extraction trials must be done for
optimal results.
Conclusion
Although correct results were not achieved, extracting Goody’s powder concept was still
understood and performed. Asprin is more acidic than acetaminophen and doesn't dissolve in
dichloromethane but in hot ethanol. Hcl neutralizes the dichloromethane aqueous base,
allowing aspirin anion to bond to an H+ and form back into solid aspirin. The extraction
process is a delicate process that requires undivided attention and should proceed cautiously.
Extraction can be an essential technique when it comes to the study of pharmaceuticals and
the creation of new drugs, as a chemist can extract or isolate different active compounds from
medicinal plants,
References
https://www.ausetute.com.au/aspirin.html#:~:text=Solubility,bonds with polar water molecules.
h-ps://www.ncbi.nlm.nih.gov/books/NBK513274/
https://www.rpharms.com/Portals/0/MuseumLearningResources/01 Drug Preparation and
Extraction.pdf?ver=2020-02-06-154038-897#:~:text=Extraction refers to processes for,oils or juices
from plants.
Lab manual
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Material Safety Data Sheet
Understanding hazards associated with chemicals is an integral component of safe and responsible
laboratory pracJce. Please complete this sheet for
each
laboratory you conduct and a-ach the sheet at the
end of your report. A-ach mulJple sheets if using more than six chemicals.
MSDS Informa3on
Special Hazard Symbols:
OX – Oxidizer
Chemical name
ConcentraJon (if a pure solid,
liquid or gas, write “pure”)
Amount (mass
or volume)
Complete the Hazard
Diamond
Dichlormethane
Pure liquid
8 mL
HEALTH
2
FLAMIBILITY
1
REACTIVITY
SPECIAL HAZARD
HCl
Liquid
2mL
HEALTH
3
FLAMIBILITY
0
REACTIVITY
1
SPECIAL HAZARD
Ethanol
Liquid
6mL
HEALTH
2
FLAMIBILITY
3
REACTIVITY
0
SPECIAL HAZARD
NaOH
Liquid
2mL
HEALTH
3
FLAMIBILITY
0
REACTIVITY
0
SPECIAL HAZARD
HEALTH
FLAMIBILITY
REACTIVITY
SPECIAL HAZARD
HEALTH
FLAMIBILITY
REACTIVITY
SPECIAL HAZARD
SA – Asphyxiant
W - No Water
GHS
GHS is an acronym for
The Globally Harmonized System of Classification and Labelling of
Chemicals
. The GHS is a system for standardizing and harmonizing the classification and
labelling of chemicals. It is a logical and comprehensive approach to:
■
Defining health, physical and environmental hazards of chemicals;
■
Creating classification processes that use available data on chemicals for
comparison with the defined hazard criteria; and
■
Communicating hazard information, as well as protective measures, on labels and
Safety Data Sheets (SDS).
■
Place a tick next to any image that is relevant to your experiment. For example, if
you used sodium hydroxide, you would place a tick in the box containing the
corrosion image.
Health Hazard
☐
Carcinogen
☐
Mutagenicity
☐
ReproducJve Toxicity
☐
Respiratory SensiJzer
☐
Target Organ Toxicity
☐
AspiraJon Toxicity
Flame
☐
Flammable
☐
Pyrophorics
☐
Self-HeaJng
☐
Emits Flammable gas
☐
Self-ReacJves
☐
Organic peroxides
Exclama3on Mark
☐
Irritant (skin and eye)
☐
Skin SensiJzer
☐
Acute Toxicity
☐
NarcoJc effects
☐
Respiratory Tract irritant
☐
Hazardous to Ozone Layer
(Non-Mandatory)
Gas Cylinder
☐
Gaseous Under
pressure
Corrosion
☐
Skin Corrosion/ Burns
☐
Eye Damage
☐
Corrosive to Metals
Exploding Bomb
☐
Explosives
☐
Self-ReacJves
☐
Organic Peroxides
Flame Over Circles
☐
Oxidizers
Environment
(NonMandatory)
☐
AquaJc toxicity
Skull and Crossbones
☐
Acute toxicity (fatal or toxic)
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Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning