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Chemistry2 3
Chemistry2 3
Table of Contents
Introduction:.......................................................................................................... 3
Standard Procedure:.............................................................................................. 4
Two other variations occurred to the above procedure. They were:...................4
Variation 1 Procedure:..................................................................................... 4
Variation 2 Procedure:..................................................................................... 4
Recrystallise Procedure:..................................................................................4
Vacuum Filter Procedure:.................................................................................4
Ferric Chloride Test Procedure:........................................................................5
Results:.................................................................................................................. 6
Graphs:............................................................................................................... 6
Yield:................................................................................................................... 7
Analysis and Discussion:........................................................................................ 7
Conclusion:............................................................................................................ 9
References:............................................................................................................ 9
Appendix:............................................................................................................ 10
Theoretical yield of Original Variation:..............................................................10
Percent Yield:................................................................................................. 10
Theoretical yield of Variation 1:........................................................................11
Percent Yield:................................................................................................. 11
Theoretical yield of Variation 2:........................................................................11
Percent Yield:................................................................................................. 11
Synthesis of Aspirin Results table:....................................................................12
Original Sample:............................................................................................ 12
Variation 1:.................................................................................................... 12
Variation 2:.................................................................................................... 12
Ferric Chloride Purity Test:............................................................................. 12
Introduction:
Aspirin, Acetylsalicylic acid, functions by reducing substances in the body that
can cause pain or inflammation. Aspirin is classified as a Non- Steroidal AntiInflammatory Drug (NSAID). NASIDs are medications that reduces fevers in
higher doses anti-inflammatory effects (ADF, 2014). The most common NSAIDs
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are aspirin, ibuprofen and naproxen because they are over the counter
medications, (MNT, September 2009). Aspirin has become increasingly popular
to prevent blood clots, over the long-term, low doses can prevent heart attacks
and strokes as it acts as a blood thinner. Its also given to patients after a heart
attack to prevent recurrence and cardiac tissue death, (MNT, September 2009).
Figure 1 Aspirin Equation:
chemical reaction involving
salicylic acid and acetic
anhydride as reactants and
aspirin and acetic acid as
products, (Note that it is the
OH group of salicylic acid that
reacts with acetic anhydride
to form an ester-like product).
Aspirin is an odourless,
colourless, crystalline, weakly acidic, white powdery substance. The boiling point
of aspirin is 140oC and the melting point is 135 oC, while aspirins density is
1.40g/cm3. Aspirin is stable in dry air; in moist air it is gradually hydrolysed into
salicylic and acetic acids and when aspirin is heated to decomposition it emits
acrid smoke and fumes. The physiological effect aspirin has is that reducing
inflammation therefore reduces swelling, pain, heat, and redness (PubChem,
October 2009). Other effects is reduction in the prostaglandins, also blocks
constriction of the efferent arteriole within the glomerulus of the kidneys, this
decreases the filtration rate of your kidneys therefore compromising the kidneys
function.
Aspirin can be made using a process called esterification. Esterification occurs
when a carboxylic acid and an alcohol chemically react to produce an ester. This
reaction can be used to synthesis aspirin from salicylic acid. The theoretical yield
is the quantity of a product obtained from the complete conversion of the
limiting reactant in a chemical reaction. The limiting reagent is the one that is
completely consumed in the reaction. The limiting reagent is determined by the
relative amounts of reactants, and must be calculated for every reaction,
therefore in this case Salicylic Acid is the limiting reagent. A catalyst changes the
rate of a reaction but isnt actually absorbed in the reaction, catalyst do not
change the composition of the final product. Pure, crystalline solids have a
characteristic melting point, the temperature at which the solid melts to become
a liquid. The transition between the solid and the liquid is so sharp for small
samples of a pure substance that melting points can be measured to 0.1 oC,
(BRW, 2004). The FeCl 3 purity test, is used because Iron III reacts with one of the
possible impurities in aspirin, therefore testing the purity of the sample.
The aim of this investigation is to synthesise aspirin by a reaction between
Salicylic Acid and Acetic Anhydride with different variations and to test the purity
by melting point and the FeCl 3 test. In the standard procedure the amount of
Salicylic Acid will determine the yield mass because Salicylic Acid is the limiting
reagent. When testing purity the samples with higher amount of Acetic
Anhydride, the more pure the recrystallised aspirin sample will be.
Standard Procedure:
Using an electronic balance, 3.00g of Salicylic Acid was measured directly into a
Conical Flask (Caution: skin irritant). Using a fume hood 6ml of Acetic Anhydride
was measured in a graduated measuring cylinder (Caution: severe eye irritant
avoid skin and eye contact.) The flask was swirled to dissolve the crystals and
6ml of concentrated Sulfuric Acid was added using a dropping pipette. The flask
was swirled once again and was gradually heated in a warm water bath (60 oC)
for 15 minutes using a retort stand and clamp to prevent the flask for tipping.
Distilled water was placed in an ice bath to cool for later use. Two filter papers
were weighed and recorded then set aside. The solution was removed from the
warm water bath. 20 drops of iced distilled water was added with precision using
a dropper then 20ml of water was measured using a measuring cylinder then
stirred to dissolve. The solution was placed in the ice bath until the crystals
formed. Then the solution was filtered using the vacuum pump (using the
directions below) with the pre-weighed filter paper, when it was finished the filter
paper was removed with the product on top of it. Then the product and filter
paper were placed on the watch glassed and left to dry overnight, the next day
when the product was dried it was recrystallised (using the method below)
Variation 2 Procedure:
The Standard Procedure was followed, only changing the Salicylic Acid
measurement to 3.00g and the Acetic Anhydride measurement to 9ml.
Recrystallise Procedure:
1/4 of the sample was weighed and placed in a beaker. 10 of Ethanol was
measured in a graduated measuring cylinder then added to the sample. The
sample was then stirred and placed in a warm water bath (45 oC) until the
crystals had dissolved. 25mL of warm water (80 oC) was measured and added to
the alcohol solution. The solution was then left to cool then when the
recrystallization started it was placed in the ice bath to finish the
recrystallization. The product was then filtered (using the directions below), and
the crystals were placed on a watch glass and left to dry overnight and then the
melting point was verified.
filter paper and then the flask was rinsed making sure all the mixture was on the
paper. The aspirator was then turned on causing the liquids to filter out, the
product was then rinsed with cold water to further remove unwanted solids.
Results:
Graphs:
Degrees Celsius
140
135
130
125
118.1
120 117.2
115
110
105
100
133.5
127.4
137.2
134.4
134.5
129.8
124.5
121.9
116.9
114.9
Sample Names
Starting Temp
Finishing Temp
Measurements/ weights
Original Sample
Variation 1
Varation 2
Yield:
Theoretical yield of Original Variation:
Theoretical yield = Molar Mass A x Moles
= 3.91g aspirin
SA
Percent Yield:
Percent yield = (actual yield / theoretical yield) x 100 = (2.828g / 3.91g) x (100)
= 72.32% yield
Theoretical yield of Variation 1:
Theoretical yield = Molar Mass A x Moles
= 3.91g aspirin
SA
Percent Yield:
Percent yield = actual yield / theoretical yield) x 100 = (3.37 g / 3.91 g) (100)
= 86.18% yield
SA
= 3.91g aspirin
Percent Yield:
Percent yield = (actual yield / theoretical yield) x 100 = (2.233g/3.91g) x (100)
= 62.02% yield
Figure 6 Comparison of
water and Variation 1
Recrystallized (4)
Although
the
experiment
proved the
hypothesis
was supported, several improvements could be made to the procedure to further
ensure the experiment is a success. Firstly, because the possible loss of product
caused by transferring from one piece of equipment to another is magnified in
the percent yield the initial amount of product could be increased. This
experiment could have also been improved by reducing the number of times the
product/sample is transferred between apparatus. Another area in which this
experiment could be improved upon is the drying stage: instead of simply letting
the product in the watch glass to dry, it could potentially be stirred constantly in
order to help release trapped liquid. The experiment could be improved upon in
several ways.
The average levels of yield obtained in this experiment has not only contributed
to the experiments procedure and mechanism, but also to the experimental
flaws. Possible reasons for such a low yield could be due to many factors, such as
disturbance throughout crystallisation, incomplete reaction and overheating.
Ultimately, crystal formation is highly dependent on critical temperature and the
level of disturbance the solution was subjected to.
The theoretical yield for the original procedure was 3.91g of aspirin (see
calculations in leaning journal) this yield is the best possible outcome that can be
produced from 3g of salicylic acid in perfect condition. The amount of aspirin that
was produced was 2.828g of aspirin. Therefore the percentage yield that was
produced was 72.32%. Theoretical yield of the variation 1 procedure is 3.91g of
aspirin (see calculations in learning journal) once again this the best possible
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72.23% product yield for the original procedure, in variation 1 2.60 grams was
synthesised from a possible 3.91 grams. Thus, there was a 66.49% product yield
and 33.51% error. In variation 2 out of 3.91 grams 2.233 grams was synthesised,
hence there being 57.10% product and 43.9% error. In future, special care should
be taken for washing the crystals with the cold distilled water in order to
maximize possible yield. The products obtained were not extremely pure, with
melting points of (original sample recrystallized) 127.4 133.5 oC, (variation 1
recrystallized) 121.9 134.5oC and (variation 2 recrystallized) 134.4 137.2 oC.
The results differed greatly from the theoretical melting point of 135.0 oC and the
resalts did not melt sharply at the literature value, like an extremely pure sample
would.
References:
1. American EdSpace.com, (2015) Esterification Reaction. [online] Available
at: http://edspace.american.edu/ap7794a/wpcontent/uploads/sites/159/2015/03/Aspirin-Synthesis-Lab-Report.pdf
[Accessed 16 Aug. 2015].
2. Aspirinfoundation.com, (2015). The Chemistry of Aspirin Aspirin
Foundation. [Online] Available at: http://www.aspirinfoundation.com/history-of-aspirin/the-chemistry-of-aspirin/ [Accessed 26
Aug. 2015].
3. Bayeraspirin.com (2015). The History of Aspirin [online] Available at:
http://www.bayeraspirin.com/pain/asp_history.htm [Accessed 23 Aug.
2015).
4. Chem21Labs.com, (2015). Experiment 5 Synthesis of Aspirin. [online]
Available at: http://www.chem21labs.com/labfiles/UKY_GL04_Lab.pdf
[Accessed 16 Aug. 2015].
5. Chemicalland21.com, (2015). ACETYLSALICYLIC ACID (ASPIRIN). [online]
Available at:
http://www.chemicalland21.com/lifescience/phar/ACETYLSALICYLIC
%20ACID.htm [Accessed 13 Aug. 2015].
6. Chemspider.com, (2015). ChemSpider. [online] Available at:
http://www.chemspider.com/Chemical-Structure.2157.html [Accessed 16
Aug. 2015].
7. Csun.edu, (2015). Chemistry 51. [online] Available at:
http://www.csun.edu/~alchemy/Chem51-LACC/Labs/C51F07L12.pdf
[Accessed 16 Aug. 2015].
8. Druginfo.adf.org.au, (2015). Aspirin - Drug Prevention & Alcohol Facts DrugInfo. [online] Available at: http://www.druginfo.adf.org.au/drugfacts/aspirin-facts [Accessed 16 Aug. 2015].
9. Pubchem.gov, (2015). Aspirin | C9H8O4 - PubChem. [online] Available at:
http://pubchem.ncbi.nlm.nih.gov/compound/aspirin#section=Top
[Accessed 13 Aug. 2015].
10.Smc.edu, (2015). Aspirin Synthesis [online] Available at:
http://homepage.smc.edu/gallogly_ethan/files/Aspirin%20Synthesis.pdf
[Accessed 23 Aug. 2015].
11.Theuplbcollegestudent.blogspot.com.au, (2011). College. Work. Life
afterwards. Full Report: Synthesis of Aspirin. [online] Available at:
http://theuplbcollegestudent.blogspot.com.au/2011/05/full-reportsynthesis-of-aspirin.html [Accessed 16 Aug. 2015].
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Appendix:
MP apparatus Procedure:
Melt-Temp apparatus is used in this experiment as well in order to find the
melting point of the synthesised substance. To use this apparatus, one must use
a small glass capillary tube to scoop up a small amount of the substance and
then place this capillary tube inside the apparatus. Once this is set up, turning on
the apparatus will slowly heat up an aluminium block touching both the capillary
tube and a thermometer. By observing the substance and noting at which
temperature the substance starts to melt then what the temperature the
substance is completely melted, it is then possible to determine the range of the
melting point.
Since aspirin (from Salicylic acid) <aspirin (from acetic anhydride), salicylic acid
is the limiting reactant and acetic anhydride is the excess reagent.
Theoretical yield = Molar Mass A x Moles SA = 180.15g/mol x 0.02172 mol
= 3.91g aspirin
Percent Yield:
Percent yield = (actual yield / theoretical yield) x 100 = (2.828g / 3.91g) x (100)
= 72.32% yield
Percent Yield:
Percent yield = (actual yield / theoretical yield) x 100 = (2.60 g / 3.91 g) (100)
= 66.49% yield
Hazardous Chemicals
3g
6mL
6.492g
3.971g
1.143g
2.828g
1.783g
Variation 1:
Mass of salicylic acid used (g)
Volume of acetic anhydride used (mL)
Mass of acetic anhydride used
(1.082g/mL) used
Mas of aspirin and filter paper (g)
Mass of filter paper (g)
Mass of crude aspirin synthesized (g)
Mass of purified aspirin product
3g
9mL
9.738g
4.496g
1.125g
3.371g
1.567
Variation 2:
Mass of salicylic acid used (g)
Volume of acetic anhydride used (mL)
Mass of acetic anhydride used
(1.082g/mL) used
Mas of aspirin and filter paper (g)
Mass of filter paper (g)
Mass of crude aspirin synthesized (g)
Mass of purified aspirin product
3g
9mL
9.738g
3.406g
1.173g
2.233g
0.708g
Colour
Dark purple
Almost clear, faint purple tint
Almost clear, pink tint
Almost clear, pink tint
Almost clear, purple tint
Almost clear, faint colour
Mostly clear, slight tint
Almost clear, slight tint
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