A.

Experiment Title:
Making N- Butyl Acetate
B. Experiment Day / Date:
Friday, 1st March 2019, at 07.30 AM
C. Experiment Finish:
Friday, 1st March 2019, at 14.00 PM
D. Experiment purpose:
Understanding of making reaction of n-butyl acetate through esterification
reaction
E. Basic Theory
Esters are compounds that can be synthesized from the reaction between
carboxylic acid and alcohol. A carboxylic acid ester is a compound containing
the –CO2R group with R can be either alkyl or aryl (Fessenden and
Fessenden, 1986). The general formula for esters is' RCOOR 'where R and R'
are organic groups. One of the ester compounds is n-butyl acetate. Butyl
acetate is a compound with the molecular formula CH3COOC4H9 which has a
molecular weight of 116.16 g / mol. Esters of several long-chain carboxylic
acids are naturally present in fats, waxes and oils (Keenan, 1980).
Perry (1997) states that the physical properties of butyl acetate include
boiling 126 ˚C, melting point of -73.5 ˚C, density of 0.88 g / mL (30 ˚C),
solubility of 0.7 g in 100 grams of water, critical temperature 306 MPa,
critical pressure 3.11 MPa, and critical solubility of 0.389 m3 / mol.
Esters are neutral organic compounds; do not react with metals Na and PCl3.
Esters consisting of low molecular weight acids and alcohol are colorless
liquid compounds, slightly soluble in water with fragrant odors, and volatile.
Esters have distinctive physical properties that give a fragrant aroma or smell.
Some esters can produce fragrant fruits. But besides that esters can also
produce aromas other than fruits (Fessenden and Fassenden, 1986).
In the synthesis of esters, acetic acid releases the OH group and the
alcohol releases the H group released as H2O. The reaction is an equilibrium
reaction. Therefore, to get a lot of results, it is done with one of the excess

1
reactants, or it can also be done removing the formed ester so that the
equilibrium shifts towards the product (Carey, 1993).
Carboxylic acids react with alcohols to form esters through a condensation
reaction known as esterification (Solomons, T. W. et. al., 2014).
General Reaction:

Picture: general reaction of esterification (Solomons, T. W. et. al., 2014).

Esterification is an ester formation reaction which can be carried out by
reacting acids and alcohol in the presence of mineral acid as a catalyst (E.
Fischer method). The process is a balance. One of the factors that influence the
speed of an esterification reaction is the role of the catalyst (Setyawardhani, et
al., 2005).
The catalyst acts to reduce activation energy so the reaction will run faster.
Activation energy is the minimum energy level needed to start a reaction. If
the energy is smaller than the molecular activation energy it remains intact and
there are no changes due to collisions (Anandito, et al., 2010; Chang, 2004).
The reaction of all reactant materials was carried out by the reflux method.
Reflux is the process of separating a mixture or component from a mixture
where the basic principle of reflux is the same as distillation. In this method
all the desired liquid will end up in a solvent and all disturbing substances in
another solvent (Day and Underwood, 2002).
The testimony with reflux still produces mixed compounds, so for
separating it needs to be done by extraction methods. Extraction is the process
of moving one or more components from one phase to another. Extraction

2
 using solvents is a process of separating solute components based on the
nature of their distribution in two solvents which do not dissolve with each
other. By utilizing differences in solubility, the desired compounds can be
selectively separated (Wildan et al., 2013).
F. Tools and Materials
1. Tools
a. Beaker glass 1 piece
b. Spatula 1 piece
c. Drop pipettes 15 piece
d. Stirring Rod 1 piece
e. Reflux condenser 1 piece
f. Funnel 1 piece
g. Separate Funnel 1 piece
h. Measuring glass 1 piece
i. Rounded bottom flask 1 piece
j. Erlenmeyer 1 piece
k. Clamps and statif 1 piece
l. Stem stirrer 1 piece
m. filter paper 1 piece
n. distillation condenser 1 piece
o. heat mantle 1 piece
2. Materials
a. N-butanol 10 mL
b. Boiling stone 1 piece
c. H2SO4 concentrate 3 drops
d. Glacial acid 30 mL
e. Aquades sufficiently
f. NaHCO3 7 mL
g. MgSO4 anhydrous crystals 1 gram

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G. Lane Works
10 mL n-butanol

Poured into rounded bottom flask

Ass 1 piece of boiling stone
Add 3 drops of H2SO4 concentrate
Add 30 mL glacial acid
Setting refine
Boiled the mixture until 3 hours
Add 30 mL aquades and shake with buchner funnel
Separated

Filtrate (Lower) Recidu (Upper)

Add 1 gram of ovened MgSO4

Shale until seprataed with buchner funnel
Seprated

Filtrate Recidu

Weighed
Result

4
I. Analysis and Explanation
Making butyl acetate on this experiment was done in a put 10 mL n-
butanol (colorless solution) into a round bottom flask by adding one boiling
stone, 3 drops of concentrated H2SO4 (colorless solution) and 30 mL glacial
acid (colorless). The function of adding boiling stones is to even heat so that
the heat becomes homogeneous in all parts of the solution does not occur
bumping, for prevent explosions(bumping) caused by pressure from the gas
produced between the two the reaction is very strong. While the addition of
H2SO4 functions as an acid and catalyst. This catalyst functions as an
accelerating reaction, because this esterification reaction is classified as a slow
reaction that takes so long that it needs to be added with the help of a catalyst.
H2SO4 also accelerates the occurrence of equilibrium at a fast time. In an
esterification reaction, H+ ions from H2SO4 play a role in the formation of
esters and also play a role in reverse reactions namely hydrolysis esters. After
adding H2SO4 and glacial acid the solution become the yellow solution.
The reaction is:
𝐻2 𝑆𝑂4
CH4HgOH (aq) + CH3COOH (aq) → C5H10COO (aq) + H2O (l)

In the manufacture of n butyl acetate, butyl alcohol will donate the butyl
group, while acetic acid will donate the acetyl group to then bind to form butyl
acetate. This testimony is also known as the esterification method.
Esterification is an ester formation reaction which can be carried out by
reacting acids and alcohol in the presence of mineral acids as a catalyst
(method Fischer). The process is a balance. One of the factors that influence
the speed of a reaction esterification is the role of the catalyst. This experiment
uses the principle of reflux, that is, all desired substances will end up in a
solvent and all disturbing substances in another solvent. Reflux aims to
exchange the primary alcohol group and refine the reaction by boiling the
mixture, then condensing the steam with cooling water and returning to
evaporate into the pumpkin, the reaction at this time the equilibrium has not
been reached. After 3 hours the reflux process is stopped, the solution turns
brownish orange. The filtrate is brown solution and the residue is colorless
solution with turbid. After that the solution is cooled and the obtained

7
 distillate is taken. This experiment occurs the physical esterification reaction is
the reaction ester formation by refluxing a carboxylic acid with an alcohol
with an acid catalyst.
The next step after reflux is mixture separation based on differences in
solubility or based on the level of polarity of the substance. The extraction
process was carried out on a separating funnel containing the results of
previous reflux with 25 mL aquades and 7 mL saturated sodium bicarbonate.
Aquades function to bind polar impurities, while non-polar butyl acetate
(crude ester) will be separated, the function of aquades also to remove
dissolved salt and homogenize the solution.
The reaction with aquades is
𝑂
𝐼𝐼 + H2O (l)
𝐶𝐻3 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶 − 𝑂 − 𝐶𝐻3(𝑎𝑞)
→ 𝐶𝐻3 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝑂𝐻(𝑎𝑞) + 𝐶𝐻3 𝐶𝑂𝑂𝐻(𝑎𝑞)

While sodium bicarbonate functions to bind acetic acid from the solution and
neutralize the solution. Sodium bicarbonate solution will bind acid residual
substances because the solution is alkaline (salt base).
The reaction with sodium bicarbonate is

CH3COOH (aq) + NaHCO3 (aq) → CH3COONa (aq) + H2CO3 (aq)

H2CO3 (aq) → H2O (l) + CO2 (g)

Sodium carbonate when reacted with acid will form CO2 and H2O gas.
The shuffle done will speed up the separation process because the molecules
will move faster. The results obtained show that the crude ester is in the upper
layer, while the water is in the lower layer. This is because more water density
is 0.998 g / mL (Daintith, 2005) when compared to butyl acetate which is 0.88
g / mL (Perry, 1997).
Then anhydrous magnesium sulfate is added as much as 1 gram.
ℎ𝑒𝑎𝑡
The reaction is MgSO47H2O (s) → MgSO4 (s) +7H2O (l)

MgSO4 (s) + 7H2O (l) → MgSO47H2O (s)

8
 Anhydrous magnesium sulphate is hygroscopic, so its existence is intended to
absorb water formed from the process of witnessing. Visible appearance after
being added to the crude ester, magnesium sulfate becomes inflated because it
has absorbed water. After adding solid anhydrous magnesium sulfate to light
brown solution and smell like bananas.
J. Conclusion
The reaction between n-butanol and glacial acid form an ester. So, the reaction
called esterification. The yield of n-butyl is 26,8 %
K. References
Anandito RBK, Basito, Hatmiyarni TH. 2010. Kinetika Penurunan Kadar
Vanilin selama Penyimpanan Polong Panili Kering pada Berbagai
Kemasan Plastik. J Agrointek 4(2): 146-150.
Carey, F. 1993. Advanced Organic Chemistry Part B: Reaction a Syntesis.
London: Plenum Press.
Chang R. 2004. Kimia Dasar. Jilid 2. Edisi 3. Penerjemah: M. Abdulkadir
Martoprawiro Jakarta: Erlangga.
Day RA dan Underwood AL. 2002. Analisis Kimia Kuantitatif. Edisi IV.
Jakarta: Erlangga.
Fessenden, Ralf J.and Joan S Fessenden. 1986. Organic Chemistry, Third
edition. Belmont, California: Wadsworth, Inc.
Keenan. 1980. General College Chemistry. New York: Harper and Row
Publishers.
Perry RH. 1997. Perry’s Chemical Engineers Handbook. 7 Ed. New York: Mc
Graw Hill Book Company Inc.
Solomons, T. W. G., Craig B. Fryhle and Scott A. Snyder. 2014. Organic
Chemistry, 11th ed. New Jersey: John Wiley & Sons, Inc.
Setyawardhani AD, Yoenitasari, Wahyuningsih S. 2005. Kinetika Reaksi
Esterifikasi Asam Formiat dengan Etanol Pada Variasi Suhu dan
Konsentrasi Katalis. Jurnal Ekulibrium 4(2): 64-70.
Wildan A, Ingrid DA, Hartati I, Widayat. 2013. Proses Pengambilan
Minyak dari Limbah Padat Biji Karet dengan Metode Ekstraksi
Berpengaduk. Jurnal Momentum 9 (1): 1-5.

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L. Attachment
1. Answer of the Questions
1) What is the function of sulfuric acid, and can it be replaced with other
acids? Explain!
Answer:
The function of concentrated sulfuric acid (H2SO4) is as a catalyst to
decrease the activation energy so that the reaction equilibrium will
occur more quickly. Sulfuric acid (H2SO4) can be replaced with other
acids, provided that the catalyst is prepared from strong acids such as
hydrochloric acid (HCl).
2) Explain why the ester layer is above!
Answer:
It is because ester (n-butyl acetate) has non polar properties while
water has polar properties and the density of ester is smaller than
density of water which is underneath, so that is caused the ester layer is
in above and the water layer is in bottom.
3) Explain the function of adding saturated NaHCO3 solution and
anhydrous MgSO4!
Answer:
 The function of NaHCO3 is to bind excessive reconstitution and
neutralize the acidic solutions that are still present in the organic
phase.
 The function of MgSO4 is to bind or remove water left in the ester
4) Mention other chemicals that can be used instead of MgSO4!
Answer:
The chemical that can be used instead MgSO4 must be chemical that
include anhydrate compounds, such as CaSO4. xH2O, CaCl2. x H2O, or
NaSO4. xH2O.

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2. Documentation

10 mL n-butanol + 1 piece of boiling

stone + 3 drops of H2SO4 + 30 mL
10 mL n-butanol + 1 piece of
glacial acid (orange solution)
boiling stone + 3 drops of H2SO4
(Colorless solution)

After Boiling the

adding mixture
glacial until 3 hours
acid, the in 90oC –
solution 100oC
become
orange

After boiled, Shake the

pour the reflux, then
solution into release the
reflux and gas.
added
aquades.

11
The
Added 25
solution
mL of
will form
aquades and
two layers,
7 mL
and flow
NaHCO3
the water
then shake
phase into
again
erlenmeyer
.

The
solution
will form 2
layers, then
flow the
water Oven 2 gram of MgSO4
phase to
get the
organic
phase.
Added
MgSO4 into
Then we get
the n-butyl
12.76 gram
actetate then
n-butyl
decantation
to get the acetate
filtrate.

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3. Calculation
Yield of n-Butyl Acetate
Data : ρ C4H9OH = 0,81 g/ml (BM = 74,12 g/mol)
ρ CH3COOH = 1,092 g/mL (BM = 60,05 g/mol)
V CH3COOH = 30 mL
V C4H9OH = 10 mL
BM n-Butyl Acetate = 116 g/mol
Mass of each component :
a) m CH3COOH = ρ x V = 1,0929 g/mol x 30 mL = 32,77 gram
b) m C4H9OH = ρ x V = 0,81 g/mol x 10 mL = 8,1 gram
𝑚𝑎𝑠𝑠 8,1 𝑔
c) n C4H9OH = = 74,129 𝑔/𝑚𝐿 = 0,11 𝑚𝑜𝑙
𝐵𝑀
𝑚𝑎𝑠𝑠 32,77 𝑔
d) n CH3COOH = = 60,05 𝑔/𝑚𝐿 = 0,55 𝑚𝑜𝑙
𝐵𝑀

CH3COOH(aq) + C4H9OH(aq)  C5H12COO(aq) +H2O(l)

M 0,55 mol 0,11 mol - -
B 0,11 mol 0,11 mol 0,11 mol
S 0,44 mol - 0,11 mol
Mass of the n-butyl acetate = n x BM
= 0,11 mol x 116 g/mol
= 12,76 gram
𝑚𝑎𝑠𝑠 𝑛−𝑏𝑢𝑡𝑦𝑙 𝑎𝑐𝑒𝑡𝑎𝑡𝑒
Yield = 𝑥 100%
𝑚𝑎𝑠𝑠 𝑛−𝑏𝑢𝑡𝑎𝑛𝑜𝑙
3,4 𝑔
=12,76 𝑔 𝑥 100%

= 26,8%

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