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CHY142-Synthesis of Butyl Propionate Via Fischer Esterification
CHY142-Synthesis of Butyl Propionate Via Fischer Esterification
Sinead Camacho
500744127
CHY 142-132
Introduction
Many esters contribute widely to the food industry in artificial flavoring and to the
production of certain odors, since esters possess the characteristic of pleasant smell and taste1.
The flavor and smell of the ester butyl propionate is floral and fragrance like. There are various
uses for butyl propionate however, it is mainly used for painting, appliance coatings or for
automobile repaintings1.
Esters, an organic compound, are produced from the synthesis Fischer Esterification
reaction of a carboxylic acid with an alcohol. This reaction can also be characterized as a kind of
nucleophilic substitution reaction since the alcohol acts as the nucleophile which in turn removes
the hydroxyl group from the carboxylic acid to create an ester functional group1. The ester butyl
propionate will form using propionic acid as the carboxylic acid, and butanol as the alcohol. The
Fischer esterification is a reaction that is also acid-catalyzed and reversible. The products
and reactants are in equilibrium. Sulfuric acid is used as a catalyst for this experiment, and
during the experiment, the acid will act as a proton donor to stipulate the reaction with necessary
protons3.
Equilibrium simply means that the reaction can revert and move toward the reactant side.
To prevent this from occurring, an excess of one of the reactants will be necessary so that the
reaction can favor the product side according to Le Chatelier’s principle. This excess reactant,
propionic acid, will cause the reaction to generate more product so that it can alleviate the
amount of maximum possible yield. For this experiment, the molar ratio between the alcohol and
carboxylic acid is 1:4 as it produces a maximum possible yield of 93%4. When a large amount of
the product is generated, both the ester and water will be present. However, only the ester is the
desirable product, thus, the anhydrous magnesium sulfate dehydrating agent will be necessary in
A reflux is performed for one hour on the combined mixture of propionic acid, butanol
and sulfuric acid. The purpose of performing a reflux is to" cook" the reaction, essentially
heating the reaction of the reagents at a constant temperature without letting any of the solvent
escape to evaporation5. Heating under reflux is used in this reaction over any other method
because in order for the reaction to occur, the mixture must be heated, however, the added heat
causes evaporation5. To prevent the solvent from evaporating, a reflux condenser is used to cool
the vapor that has evaporated and sends it back down to the liquid, ultimately resulting in no loss
of the solvent. This is the advantage of performing the lab using a reflux; there is little to no loss
An extraction is also performed in this lab to separate the components of the mixture that
do not make up the ester6. Not all liquids are miscible which means that some liquids will have
different densities resulting in two layers to form even after they are mixed6. In this lab, the ester
has a lower density than water which means it is insoluble and will be the top layer of the two
phases. By using a separatory funnel and the process of extraction to separate the aqueous
separation of liquids from other impure liquids by producing vapor at different boiling points of
the compounds7. When the solution has reached the expected boiling point range of the ester,
evaporation of the pure ester will distill out. This process is completed to purify the solutions.
To test the purity of the obtained ester two tests, the refractive index and infrared
spectroscopy can be performed7. However, in this experiment, only the infrared spectroscopy is
done. Infrared spectroscopy is the analysis of the wavelength of energy (infrared light)
interacting with molecules in the substance7. The functional groups of the literature IR of the
ester is compared to the functional groups produced from the experimental ester for purity.
Butyl
130.18 C7H14O2 -89°C 146.8°C Colourless liquid Solubility is poor 0.875
Propionate
Colourless liquid
Soluble in water; and as
Butan-1-ol 74.12 C4H9OH -88.6°C 117.73°C with a strong 0.810
well as ethanol and ether
alcoholic odour
Colourless, volatile
Only slightly in water;
Diethyl Ether 74.12 C4H10O -116.2°C 34.5°C liquid with a putrid, 0.714
soluble in ethanol
sweetish odour
Colourless, oily
Sulfuric Acid 98.07 H2SO4 10°C 337°C Soluble in water 1.83
liquid
Part A –Reaction
The reflux apparatus was set up. Using two graduated cylinders and a dropper to obtain
more accurate measurements, 7.3 mL of butanol and 14.4 mL of propionic acid were obtained.
These were combined into a 250 mL round-bottom flask. 2.5 mL of sulfuric acid was added to
the flask and the contents were mixed together. Two to four boiling chips were added to the
mixture to prevent bumping as the solution was heated. A reflux was performed for one hour and
the mixture was heated at a constant temperature to produce the product of the reaction.
Part B –Separation
The reaction contents from the round-bottom flask were transferred to a separatory funnel
using a funnel. 15 mL of diethyl ether was used to wash the reaction flask to ensure all the
mixture was collected. 25 mL of distilled water was added for the first extraction to be done. The
contents were vented under the fume hood and the bottom aqueous layer was removed into a
beaker and discarded. Another extraction using 25 mL sodium bicarbonate was performed. This
extraction was done three times with the sodium bicarbonate in order for the aqueous layer to test
basic using litmus paper. Lastly, an extraction was performed with 25 mL of sodium chloride.
The organic layer was extracted into an Erlenmeyer flask and a small amount of magnesium
sulfate drying agent was added to absorb any traces of water. The flask was swirled, covered
tightly with Parafilm and stored until the next lab period.
Part C –Purification
Simple distillation apparatus was set up. The product was transferred to the distillation
flask using filter paper and a funnel and two to four boiling chips were added. The solution was
heated firstly to the boiling point of diethyl ether in order for all the ether to evaporate out. This
was collected in a small beaker. Once signs showing the distillation had stopped, the remaining
solution was heated to the boiling point of the alcohol followed by the boiling point of the acid
and then finally, the boiling point of the ester. The ester product was collected into a pre-weighed
beaker and was weighed to determine the amount of ester obtained. Infrared spectroscopy was
done to determine the purity of the ester. A few drops of the sample were placed onto the center
of the Agilent Cary 630 spectrophotometer using a Pasteur pipette and the spectrum of the
sample was created through the software. The results were obtained and then transferred to a
USB.
Propionic
14.4 mL 141.15°C N/A
Acid
Butyl
0.8 g 146.8°C N/A
Propionate
Figure 1: Literature Infrared Spectrum of Functional Groups of Butyl Propionate8
Discussion
When making esters through the Fischer Esterification reaction, a carboxylic acid and an
alcohol are the main reactants involved. In this lab, the acid was the excess reagent and the
alcohol was the limiting reagent. This was determined based on the prices of the reagents.
According to the data from the laboratory manual, the acid exhibited a lower price of $47.60
compared to the alcohol which was $74.20 therefore, more of the cheaper reagent and less of the
more expensive reagent were used, and this allowed the lab to be more cost efficient.
During the distillation of butyl propionate, diethyl ether was produced through the
condenser at a boiling point range of 28-34°C. The boiling point range of butyl propionate is
146.8°C (Table 1) therefore, the ether had a range that was lower and more broad and proved
that it was very impure and did not contain contents of the ester. Following the ether came the
butanol and this was produced at a boiling point range of 100-109°C. Attempts to get the
temperature to rise to the boiling point of the propionic acid were to no avail and in turn, led to
no formation of the butyl propionate product through the condenser. The heating mantle was
dropped and this allowed all the condensation to form back to liquid in the flask. After the
distillation was completed, the product that was left in the flask was weighed in a pre-weighed
beaker and the mass was determined. From the initial 10g of butyl propionate that was supposed
to be created, only 0.8 g was produced. This led to a percent yield of 8%, which was much too
Infrared spectroscopy was performed to further determine the purity of the ester
produced. When comparing the experimental butyl propionate IR to the literature IR, the overall
shape of the spectrum is almost exact except for a few extra peaks in between and on the right
side. However, these extra peaks weren’t taken into much consideration when analyzing, and
may have been due to some impurity from the collected ester. The peaks that were evidently
similar were the functional groups that make up the ester. These functional groups are displayed
on Figure 2 and are provided in Table 3. They provide evidence for the purity of the collected
sample. The literature position ranges for the CH3 and C-H alkane functional groups is 2840-
3000 cm-1. The experimental position for these groups were 2959.548 cm-1 and 2874.669 cm-1
respectively, which clearly shows that they are within the acceptable range. A C=O aldehyde
functional group is also observed at sample position 1736.068 cm-1. This functional group also is
within its acceptable literature range of 1720-1740 cm-1. Lastly, the main functional group of
butyl propionate, an ester, can be observed. The literature position for the C-O ester functional
group is 1163-1210 cm-1 and the sample position was shown at 1182.665 cm-1. The presence of
an OH functional group is what really makes the final product stand out. The absence of an OH
peak in the spectrum indicates that the product went through completion to an ester. All in all,
from the data provided, it shows that the functional group positions are within their acceptable
ranges and when looking at both IR spectrums, the similarities of the functional groups that make
up butyl propionate indicate that the collected sample from the experiment is pure.
Sources of error are sometimes inevitable during laboratory experiments. The low percent
yield could have been due to loss of product during extraction of the aqueous layers and/or that
the reaction may have not gotten enough time to reflux in order to complete the reaction, which
led to less product being collected and more starting material separating out during extraction.
The low yield could have also been due to the evaporation of the product while left stored for a
week, and due to errors in equipment such as a loose joint between the condenser and the flask,
which may have caused the product to escape as vapor. Some product could have also been lost
during transfers between glassware. The actual boiling point of butyl propionate is 146.8°C. The
experimental boiling point temperature was not determined as the temperature was not rising
above 109°C. Impurities such as diethyl ether, alcohol, acid or water left in the solution could
have altered the boiling point and prevented the temperature from rising. These impurities can
also be the cause of the extra peaks in the experimental IR spectrum. This experiment can be
improved by adding more amounts of one of the reactants, in this case the acid, so that the
reaction can go to the right and drive more product. Newer equipment can also be used to
facilitate better results and more time to for the reaction to go to completion should be given.
Conclusion
The purpose of this lab was to synthesize 10g of the ester butyl propionate from a
carboxylic acid and an alcohol. Propionic acid and butanol were identified as the best reagents to
use, making the acid the excess reagent and the alcohol the limiting reagent. Looking over the
data collected, it is evident that a pure sample of butyl propionate was produced since the peaks
from the spectrums and the presence of major functional groups indicate pure results. Although
the percent yield was only 8%, it is fair to say that the lab was completed with limited success
based on the amount of ester produced, but successful in producing a pure sample of butyl
propionate.
References
1
Ksolv Chemical Distribution. Home Page. Butyl Propionate (2012).
http://www.ksolv.com/index.html
2
David R. Lide, ed., CRC Handbook of Chemistry and Physics, Internet Version 2005,
chemistry.org/
4
Department of Chemistry & Biology. CHY142 Organic Chemistry Laboratory Manual
6
Raydo, L. Margaret; Church, S. Meagan; Taylor, W. Zane; etc,. Liquid-Liquid Extractions
139-142.
7
Gelosa, D.; Sliepcevich, A. Chemical Laboratory Techniques. Fundamentals of Chemistry 2015.
8
Spectral Database for Organic Compounds SDBS. Butyl Propionate. National Institute of
July 2016,
chem.libretexts.org/Reference/Reference_Tables/Spectroscopic_Parameters/Infrared_Spe
ctroscopy_Absorption_Table.