ORGANIC

CHEMISTRY LABORATORY I
BSK1402

LAB REPORT

EXPERIMENT 5: Esterification of butanol with acetic

acid

_________________________________________

NAME Fathul Aiman Bin Fahmi

MATRIX NO. Sa18094
SECTION 02
DATE
 ABSTRACT

The objective of this experiment is to Esterification of butanol with acetic acid by using
different apparatus which ii ordinary apparatus and dean and stark apparatus. Acetic acid and
butanol are used the reactants with the presence of sulphuric acid in this experiment. Then , the
butanol and acetic has been mixed in the flask with the presence of the sulphuric acid as catalyst
and been heated up for 1 hour and the mixture start to evaporated which is condenses and runs
down back to the flask but for the Dean & Stark apparatus. The vapor has been run down to
the sidearm, which is closed with a cork forming two layers. The layers are separate, with the
denser layer remaining in the sidearm while the lighter layer runs down into the reaction flask.
Then, the smell and the purity of the results of the two reaction has been identified and has
been the percent has been calculated.
INTRODUCTION

Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an
alcohol or phenol. Esters are ubiquitous. Most naturally occurring fats and oils are the fatty acid esters
of glycerol. Esters with low molecular weight are commonly used as fragrances and found in essential
oils and pheromones. Their flexibility and low polarity is manifested in their physical properties; they
tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the
corresponding amides. This chapter analyses the separation of esters of carboxylic acids and
determines the mass spectra focusing on molecular ion and fragmentation. Accurate mass
measurement data would establish the presence of oxygen, especially in the ions represented by the
more intense peaks. Determination of the double-bond position in C10-C24 monounsaturated methyl
or ethyl esters is also discussed. The molecular ion peaks are intense with characteristic fragment ions
represented by peaks at m/z 70, 98, and 113.
 METHODOLOGY

1-butanol and acetic Two or three anti-

acid is placed in the flask bumping granules are
The mixture then is
along with an acid added to the mixture
heated up to reflux
catalyst concentration and fit in to the reflux set
H2SO4 up.

The reflux has been run

The percent of product The volume of product
up for 1 hour until nor
has been calculated. has been collected
more layer are produced.
 RESULT

Type of apparatus Normal Dean and stack

Organic Volume 17 15
Aqueous Volume 4 3
Total Volume 21 18

Calulation

1. Molarity of H2SO4 =97/100 x 1 mol/98.079g X 1.84g/1ml X 1000mL/1L

=18.02M

2. Molarity of Acetic Acid = 100/100 X 1mol/60.052g X 1.049g/1mL X 1000ml/1L

=17.47M

3. Molarity of 1-butanol = 85/100 X 1 mol/74.121g X 0.81g/1mL X 1000mL/1L

=9.29M

3. Mol of acetic acid= volume X molarity

=0.01L X 17.47 g/mol
5. Mol 1-butanol = Volume X molarity

=0.01L X 9.29 g/mol

= 0.929

6. Mass of butyl=acetate = 0.0929mol X 116.16 g/mol

=10.79g

7. Volume butyl acetate =10.79g/882(g/L)

= 0.01223 L

=12.23 Ml

8.Dean and stack apparatus = (12.23 – 3 mL)/12.23 x 100 = 75.47%

Normal apparatus = (12.23 – 4) /12.23 X 100 =67.2 %

 DISCUSSION

Acetic acid and butanol are used as the reactants with the presence of sulphuric acid in this
anti-bumping granules are added to promote smooth boiling and to prevent bumping of the
solvent. As mention at the above, the esterification is slow and reversible process so it is
distilled for one hour and hence more ester could be generated. experiment. The esterification
reaction is take place as the diagram 1 below. The experiment was conducted using 2 apparatus
which is ordinary apparatus and Dean & Stark apparatus. For the Dean and stark, the reaction
flask has been heated and the vapor travels out of reaction flask up into the condenser where
water being circulated around it causes it to cool and drip into the distilling trap. Here, the
immiscible liquids separate into layers (water below and solvent above it). When their
combined volume reaches the level of the side-arm, the upper, less-dense layer will begin to
flow back to the reactor while the water layer will remain in the trap. The trap will eventually
reach capacity when the level of the water in it reaches the level of the side-arm. At this point,
the trap must be drained into the receiving flask. The process of evaporation, condensation and
collection may be continued until it ceases to produce additional amounts of water. After reflux
for one hour, the product has been collected the percent yield obtained for dean and stark is
75.47 % while for the normal apparatus are 67.2%. It can conclude that the dean and startk
apparatus are more effective compare than normal apparatus.

Diagram 1: Reaction between acetic acid and butanol

Diagram 1 shows the Fischer esterification reaction reaches equilibrium can be shifted by
adding more of the acid or of the alcohol, depending on cost or availability. The mechanism of
the reaction involves initial protonation of the carboxyl group attack by the nucleophilic
hydroxyl, a proton transfer, and loss of water followed by loss of the catalyzing proton to give
the ester.
 CONCLUSION

It can conclude that the dean and stark apparatus are more effective than normal apparatus thus
the normal apparatus took up at least 3 hour for the reaction occur to get the product. The small
of product are identified smell like..In addition this experiment addressed two green chemistry
principles that helped increase the efficiency of the reaction while minimizing waste in the
environment. The first one is that the H2SO4 catalyst was used to speed up the reaction because
they are superior stoichiometric reagents. Likewise, this experiment provided an organic
solvent free procedure which prevented waste.
 APPENDIX

Picture 1: Esterification process using dean and stark apparatus