Salicylic acid syntesis

Surname 1
Surname
Name of Professor
Course
Institution
Date
Synthesis of Salicylic acid
Introduction
The experiment was carried out to describe the synthesis of salicylic acid using methyl salicylate
(wintergreen oil). The method of heating under reflux was used. The chemical reaction that
occurred was summarized in the figure below;
Figure 1: Chemical reaction for synthesis of salicylic acid
Procedure
The heating under reflux was apparatus set up. Ten (10) ml of methyl salicylate, 5 ml of NaOH,
boiling chips were added to a boiling flask. The boiling flask was heated and the mixture allowed
to boil for thirty minutes until the oily matter disappeared. The original mass of methyl salicylate
was 1.53g, and after the boiling, a white solid was formed. Care was observed while performing
Surname 2
the experiment because of the reagents (sulfuric acid and methyl salicylate are corrosive and
hazardous). The product (salicylic acid) is also an irritant and hazardous material. The solution
was transferred into a beaker without the solids. 16ml of 3M sulfuric acid was added while stirring
was continued. The pH level was lowered to 2, and the solution was cooled in an ice bath for 10
minutes. The product (salicylic acid) was filtered using the vacuum filtration wetted with cold
water. The product was purified by recrystallization vacuum filter and then dried.
Results and Discussion
Mass before crystallization
Item
Mass in grams
Filter paper
0.19
Watch glass
39.13
Total
40.96
Salicylic acid
1.64
Mass After crystallization
Item
Mass in grams
Watch glass
39.14
Total
40.42
Salicylic acid
1.28
Melting point Analysis for salicylic acid
Surname 3
Trial
Start temperature
Stop temperature
Trial 1
158.6
160.0
Trial 2
158.9
160.9
Calculations
% π‘Œπ‘–π‘’π‘™π‘‘ π‘π‘Žπ‘™π‘π‘’π‘™π‘Žπ‘‘π‘–π‘œπ‘›π‘ 
π‘€π‘Žπ‘ π‘  π‘Žπ‘“π‘‘π‘’π‘Ÿ π‘Ÿπ‘’π‘π‘¦π‘π‘Ÿπ‘¦π‘§π‘Žπ‘‘π‘–π‘œπ‘› = π‘‡π‘œπ‘‘π‘Žπ‘™ π‘šπ‘Žπ‘ π‘  βˆ’ π‘€π‘Žπ‘ π‘  π‘œπ‘“ π‘€π‘Žπ‘‘π‘β„Ž π‘”π‘™π‘Žπ‘ π‘ 
=
(
40.42 βˆ’ 39.14
)
𝑔
= 1.28𝑔
% π‘Œπ‘–π‘’π‘™π‘‘ =
1.28
1.381
π‘₯ 100%
= 92.69%
% π‘…π‘’π‘π‘œπ‘£π‘’π‘Ÿπ‘¦ π‘π‘Žπ‘™π‘π‘’π‘™π‘Žπ‘‘π‘–π‘œπ‘›π‘ 
% π‘…π‘’π‘π‘œπ‘£π‘’π‘Ÿπ‘¦ =
1.28
1.64
π‘₯ 100%
= 78.05%
π‘€π‘Žπ‘ π‘  π‘Žπ‘“π‘‘π‘’π‘Ÿ π‘Ÿπ‘’π‘“π‘™π‘’π‘₯ =
(
40.96 βˆ’ 39.32
)
𝑔
= 1.64𝑔
𝑀𝑒𝑙𝑑𝑖𝑛𝑔 π‘π‘œπ‘–π‘›π‘‘ π‘Ÿπ‘Žπ‘›π‘”π‘’
Surname 4
Start Temperature (
o
C)
Stop Temperature (
o
C)
Salicylic acid
158.6
160.0
Salicylic acid +salicylic acid
from benzene
158.9
160.9
π‘€π‘Žπ‘ π‘  π‘œπ‘“ π‘šπ‘’π‘‘β„Žπ‘¦π‘™ π‘ π‘Žπ‘™π‘–π‘π‘¦π‘™π‘Žπ‘‘π‘’ = 10π‘šπ‘™ π‘₯
1
1000
π‘₯
152.1
1
= 1.521𝑔
π‘‰π‘œπ‘™π‘’π‘šπ‘’ π‘œπ‘“ π‘œπ‘“ π‘šπ‘’π‘‘β„Žπ‘¦π‘™ π‘ π‘Žπ‘™π‘–π‘π‘¦π‘™π‘Žπ‘‘π‘’ = 1.521𝑔 π‘₯
1
1.174𝑔
= 1.296π‘šπ‘™
π΄π‘šπ‘šπ‘œπ‘’π‘›π‘‘ π‘œπ‘“ π‘Šπ‘Žπ‘‘π‘’π‘Ÿ π‘œπ‘“ π‘Ÿπ‘’π‘π‘Ÿπ‘¦π‘ π‘‘π‘Žπ‘™π‘™π‘–π‘§π‘Žπ‘‘π‘–π‘œπ‘› = 1.331𝑔π‘₯
100π‘šπ‘™
6.7𝑔
= 20.6𝑙
Discussion
Every reaction has its unique rate of reaction. The organic reactions are typically slower than the
other reactions. The organic reactions are slower because of the breaking of more covalent bonds
that make the process slow. Heating was necessary to speed up the rate of the reaction. The heating
under reflux meant mixing reagents and heating them while a condenser was attached at the top to
stop the vapor from the solution from leaving the system. The experiment was purposed to extract
the salicylic acid from the wintergreen oil by heating under reflux then followed by
recrystallization for purification.
Error Analysis
Surname 5
The results obtained were susceptible to errors resulting from insufficient time for reaction to be
complete. The reaction involved was organic and therefore occurred at a slow rate. Enough time
would be allowed to improve the percentage yield and the recovery yield. Failure to allow enough
reaction time may have led to incomplete reaction and hence some reactant remained mixed with
the product as impurities. Insufficient time in the ice bath could have also led to low percentage
recovery. During recrystallization, failing to add sufficient sulphuric acid could have also brought
up errors in the % yield; by lowering the purity level. Another source of error could have been the
reagent contamination that would have reduced the purity of the reagents and affect the results.
Conclusion
The synthesis of salicylic acid from methyl salicylate was achieved through the process of heating
under reflux. Sodium hydroxide was used to act as a catalysts. In the purification, the
recrystallization process was carried out with addition of sulphuric acid. During the experiment,
care was taken to avoid making eye, skin and oral contacts with the corrosive reagents and
products. After heating the methyl salicylate-sodium hydroxide mixture, white solids of salicylic
acid were observed. After the heating under reflux, 1.64g of the salicylic acid was obtained. The
% yield of the product was 92.69%. However, after recrystallization, the mass of the product was
1.28g and translated to 78.05% recovery yield. Therefore after allowing enough time and doing
more recrystallization, the ratio of the product; yield would be 1:1. Moreover, the melting
temperature range for the experiment was 158.6-160.0
o
C; which was closer to the theoretical value
of 159
o
C. The possible sources of errors could be the allowing less time for the reaction and
contamination of the reagents.

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