OBJECTIVE

 To convert ethanol to ethyl acetate ( ethyl ethanoate )

ABSTRACT

The conversion of ethyl alcohol to ethyl acetate provides a synthesis step to convert raw
material such as ethanol to ethyl acetate and the reaction involved is called esterification. In
this experiment‚ acetic acid will be react with an alcohol to produce ester plus water and this
is known as Fisher esterification. A mineral acid such as sulphuric acid also used as a
catalyst. This experiment was divided into three steps which is reflux‚ distillation and
neutralization. During neutralization‚ sodium carbonate solution has used to distilled contains
traces of acetic acid. Anhydrous calcium chloride also acts as drying agents to absorb the
water from the ethyl acetate. Percentage yield has calculated based on the ratio of actual yield
to theoretical yield to compare how much product should get from running a reaction against
how much that actually got.
 INTRODUCTION

Chemist use organic synthesis both to make larger amounts of useful natural compounds and
to invent totally new compounds in search of improved properties and biological effects. This
experiment provides a synthesis step to convert raw material such ethanol to ethyl acetate.
Reaction involved is called esterification.

The reaction of a carboxylic acid with an alcohol to produce an ester plus water is known as
the fisher esterification reaction. A mineral acid, usually sulfuric acid is used as a catalyst.

CHEMICALS

 Ethanol
 Glacial acetic acid
 Conc. Sulfuric acid
 30% sodium carbonate solution
 Calcium chloride
 Granular anhydrous calcium chloride
 Anti-bumping granules

APPARATUS

 Round bottom flask

 Water /liebig condenser
 Retort stand
 Separating funnel
FLOW CHART
 RESULTS

Volume of ethanol : 50.00 ml

Weight of ethanol : 38.74 g

Volume of acetic acid : 50.00 ml

Weight of acetic acid : 50.41 g

Theoretical yield : CH3COOH + C2H5OH <–> CH3COOH + H2O

1 𝑚𝑜𝑙 𝑒𝑡ℎ𝑎𝑛𝑜𝑙 1 𝑚𝑜𝑙 𝐶𝑂𝑂𝐻 60 𝑔 𝐶𝑂𝑂𝐻
= 38.74 g eth× ×1 𝑚𝑜𝑙 𝑒𝑡ℎ𝑎𝑛𝑜𝑙×1 𝑚𝑜𝑙 𝐶𝑂𝑂𝐻
46 𝑔 𝑒𝑡𝑎ℎ𝑛𝑜𝑙

= 50.53 g ( limiting reagent )

1 𝑚𝑜𝑙 𝐶𝑂𝑂𝐻 1𝑚𝑜𝑙 𝐶𝑂𝑂𝐶2𝐻5 88 𝑔 𝐶𝑂𝑂𝐶2𝐻5
= 50.41g COOH× × ×1 𝑚𝑜𝑙 𝐶𝑂𝑂𝐶2𝐻5
60 𝑔 𝐶𝑂𝑂𝐻 1𝑚𝑜𝑙 𝐶𝑂𝑂𝐻

= 73.93 g COOC2H5

Weight of receiving flask : 34.17 g

Weight of Product + receiving flask : 51.20 g

Weight of ethyl ethanoate : 17.03 g

( Actual yield )
𝐴𝑐𝑡𝑢𝑎𝑙 𝑦𝑖𝑒𝑙𝑑
Percentage yield : % yield = × 100
𝑇ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙 𝑦𝑖𝑒𝑙𝑑

17.03
= × 100
83.29

= 20.45 %
 DISCUSSION

This experiment was about conversion of ethyl alcohol to ethyl acetate by using synthesis
step. The reaction that involved is called esterification. Acetate is the ester that an organic
group replaces a hydrogen atom in -OH group of acetic acid through reaction (typically
condensation) with alcohols. Condensation is the reaction in which two molecules having -
OH groups are joined with eliminating a water molecule from their -OH groups. They are
produced by esterification reaction from acetic acid and the corresponding alcohol in the
presence of strong acids like sulphuric acid. This reaction is reversible and acetate can be
hydrolyzed back into alcohol and acetic acid in the presence of strong bases or strong acid,
especially at elevated temperature. The reaction of a carboxylic acid such as acetic acid with
an alcohol such as ethanol to produce an ester like ethyl acetate plus water is known as Fisher
Esterification. This experiment was divided into three step which is reflux‚ distillation and
neutralization.

First, for the reflux‚ acetic acid will be react with ethanol by using sulphuric acid as a catalyst
to produce ethyl acetate and water. This is an equilibrium reaction:

CH3COOH + C2H5OH <–> CH3COOH + H2O

Simply adding the reagents will not produce a good yield of ethyl acetate because this is an
equilibrium. However, by refluxing and by having an acid catalyst, one can obtain a
significant amount of ethyl acetate. But the reaction still not produce the pure product. After
reflux‚ one is left with a mixture of ethyl acetate, water, acetic acid and ethanol. This allows
for a multitude of azeotropes. So the second step that must be follow was distillation.

During distillation‚ the first thing to come out was ternary azeotrope. This causes a mixture of
ethanol, water and ethyl acetate to comes over. The ethanol that gets removed did not form
any ethyl acetate, so the ethanol will get wasted. However, the percentage of ethanol that
comes over is way too low compared to the percentage of ethyl acetate and water that comes
over. This effectively shifts the equilibrium to the right.

At some point, almost all ethanol is going to be consumed as the ethanol either gets distilled
away or reacts to form ethyl acetate. That was one of the reasons to have excess acetic acid
present, which allows more ethanol to react in the equilibrium. At this point, the azeotropic
mixture of ethyl acetate and water should start to distilled off. The percentage of ethyl acetate
that distilled over in both azeotropic mixtures is much higher than any other compound. At
some point, the ethyl acetate is going to get all distilled over.

When all ethyl acetate is distilled, the temperature suddenly rises. This is because water is
going to start to be distilled over (100ºC) and the distillation should be stop. The relatively
high boiling point of acetic acid prevents it from distilling over. The ethyl acetate that is
collected is contaminated with water and ethanol and some of acetic acid may also be present.
The ethanol present aids preventing the hydrolysis of ethyl acetate.
The third step which is neutralization was the last step that needs to be done to get the pure
product. The neutralization involved ethyl acetate with sodium carbonate in order to remove
the acetic acid present. In order‚ to remove the ethanol and water present in the ethyl acetate‚
distilled has washed with water. This effectively removes the ethanol present and some of the
product gets lost. After removing the ethanol, it is necessary to remove the water present by
distilling with a drying agent. Calcium chloride has used in this experiment because the
calcium chloride can form a multitude of hydrated species effectively absorbing the water
from the ethyl acetate. In this case, calcium chloride forms the dehydrated, which only
decomposes at around 175ºC. This allows to distilled the ethyl acetate and effectively remove
the water from ethyl acetate.15 grams of calcium chloride can absorb approximately 5 grams
of water, in the conditions given. However, the quantity was added a little bit to make sure
the product gets as anhydrous as possible and recycle the calcium chloride. The collected
product gained was 17.03 g and represent the actual yield while the theoretical yield was
83.29g. After calculation had made‚ the percentage yield obtained from this experiment was
20.45%.
 CONCLUSION

The percent yield for the experiment is 23.45%. Some possible sources of error could have
contributed to this. First off, a small amount of the acetic acid did not make into the round-
bottomed flask as did not weighed accurately. While separating the layers, it gauge when to
close the stopcock perfectly, so that led to a loss of eventual product. Moreover, while
separating the layers using the separating funnel, maybe there was some emulsion in the
mixing, so the product may be lost as the layers did not completely separate. Also, some of
the ester might evaporated during reflux or the ester left from the solution inside the distilling
flask. If water was removed from the reaction mixture, it was cause equilibrium to shift
towards ethyl acetate to make water and thus lead to an increased conversion of acetic acid to
ethyl acetate. When a compound on one side of the reaction is removed, equilibrium will shift
towards the side it was removed from. If more of a compound is added to one side, then
equilibrium will shift towards the other side.

RECOMMENDATION

In order to obtain accurate results, there are a few recommendations that should be taken in
the next experiment. First and the most important step is, all the glassware should be rinse
properly to avoid contaminant. Contamination of glassware is perhaps the most common
cause of poor results when making observations. Also, it is important to make sure that eyes
is perpendicular to the meniscus level during taking the reading of the result. The round
bottomed flask and it content should be cool sufficiently after reflux to avoid some loss of
material by the evaporation. Moreover, the separating funnel should be close and shaken
gently by inverting the funnel multiple times, if the two solutions are mixed together too
vigorously emulsions will form.
 TUTORIALS

1. (a) Write and balance the equation for the reaction for the reaction of acetic acid with
ethanol to produce ethyl ethanoate and water.

CH3COOH + C2H5OH <–> CH3COOH + H2O

(b) In the reaction of above example, how many grams of ethyl ethanoate would be
produced if 50 ml of ethanol were react with 50 ml acetic acid ? Which is the limiting reagent
? ( Given 𝑝𝑒𝑡ℎ𝑎𝑛𝑜𝑙 : 0.8 g/ml and 𝑝𝑎𝑐𝑒𝑡𝑖𝑐 𝑎𝑐𝑖𝑑 : 1.06 and 𝑝𝑒𝑡ℎ𝑦𝑙 𝑎𝑐𝑒𝑡𝑎𝑡𝑒 : 0.9 g/ml )

Mole = mass / molar mass

Mol of ethanol = ( 50 ml × 0.8 g/ml ) ÷ 46 g/ml

= 0.869 mol of ethanol

Mol of acetic acid = ( 50 ml × 1.06 g/ml ) ÷ 60 g/mol

= 0.883 mol

So, 0.8683 mole of ethanol would react completely with 0.869 × ( 1×1 ) = 0.869 mole of
acetic acid present than that, so acetic acid is excess and ethanol is limiting reagent.

(0.869 mol ethanol) × ( 1 mol ethyl ethanoate / 1 mol ethanol ) × (88.1051 g ethyl ethanoate
/mol) = 76.5 g

(c) Calculate the percentage yield if 50.0 g of ethyl ethanoate was obtained from the
experiment.

Percentage yield = ( actual yield / theoretical yield ) × 100

= ( 50 g ) / ( 76.5 g ) × 100 = 65.4 %

2. What is the function of reflux water condenser ?

To prevent the solvent from boiling away, a reflux condenser is used. This is a glass column
with a second column surrounding through which cool water flows. As vapour from the
boiling solvent rises into inside column of the reflux condenser, it is cooled by the jacket of
water on the outside and condenses.

3. Why must the concentrated sulphuric acid be added slowly and with cooling

The concentrated sulphuric acid on dilution gives out a lot of heat, the slow addition with
cooling is necessary to avoid splashing if the mixture gets hot.
4. What is the function of sodium carbonate solution and anhydrous calcium chloride ?

Sodium carbonate : The distillate contains traces of acetic acid and perhaps some sulphuric
acid. Sodium carbonate solution remove this.

Anhydrous calcium chloride : drying agent absorbing the water from the Ethyl Acetate.

5. Explain the phenomena of 2 layers formed in the separating funnel

A separatory funnel, also known as separation funnel, separating funnel, or colloquially sep
funnel, is a piece of laboratory glassware used in liquid- liquid extractions to separate the
components of a mixture into two immiscible solvent phases of different densities. Typically,
one of the phases will be aqueous, and the order a non-polar lipophilic organic solvent such
as ether, MTBE , dichloromethane, chloroform, or ethyl acetate. All of these solvent is form
a clear delineation between the two liquid. The two layers formed are usually known as the
organic and aqueous phases. Most organic solvents float on top an aqueous phase, though
important exceptions are most halogenated solvents. The organic solvent used for the
extraction must not react with the substances to be extracted or with water. It should also
have a low boiling point so it can be easily removed from the producted.

REFERENCES

 Lab Manual