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Hydrolysis of Methyl Acetate

LORENZ JOHN T. CHU

BS Chemical Engineering | College of Engineering and Architecture | Department of Chemical Engineering Cebu Institute of Technology - University, N. Bacalso Ave. Cebu City,

6000 Philippines

ABSTRACT

Chemical kinetics is that branch of chemistry which deals with the study of the speeds or the rates
of chemical reactions, the factors affecting the rates of the reactions and the mechanism by which
the reactions proceed. It concerns itself with the measurement of rates of reactions proceeding
under the given conditions of temperature, pressure and concentration. For this experiment, the
specific rate constant at two or more given temperature were to be determined. The aliquots
gathered from different time intervals were titrated with 0.212N NaOH. The rate of reaction of the
hydrolysis of methyl acetate was measure at 25C and 35C. The average rate of reaction obtained
at 25C is 0.111/min while at 35C is 0.132/min.

1. Introduction

Chemical kinetics is the study and discussion of chemical reactions with respect to reaction
rates, effect of various variables, re-arrangement of atoms, formation of intermediates etc. In
chemical kinetics, the term rate of reaction refers to the time rate of change, dc/dt, of the
concentration of some constituent of interest. The reaction-rate-constant, or specific reaction rate,
k, is a proportionality factor which relates the rate of reaction to reactant concentrations on which
it depends.
A first order reaction is a reaction that proceeds at a rate that depends linearly on only
one reactant concentration. As such, a first-order reaction is sometimes referred to as
a unimolecular reaction. While other reactants can be present, each will be zero-order, since the
concentrations of these reactants do not affect the rate. Thus, the rate law for an elementary
reaction that is first order with respect to a reactant A is given by:

= =

For the first-order reaction, k is numerically equal to the fraction of the substance which
reacts per unit time, and is usually expressed in reciprocal seconds or minutes. It should be notes
that for a first-order reaction, the specific reaction rate can be determined without information on
the initial reactant concentration or even as to the absolute concentration at various times, provided
that a quantity directly proportional to the concentration can be determined.

The kinetics of a second-order reaction is described by the equation


= =

The hydrolysis of methyl acetate presents a number of interesting kinetic aspects. The
reaction, which is extremely slow in pure water, is catalyzed by hydrogen ion. Hydrolysis is a
reaction involving the breaking of a bond in a molecule using water. The hydrolysis of methyl
acetate produces acetic acid and methanol. The reaction is:

CH3COOCH3 + H2O = CH3COOH + CH3OH

In this experiment, the rate of reaction constant/specific rate constant of the hydrolysis of
methyl acetate at two different temperatures was determined.

2. Materials and Methods

2.1 Materials

Methyl Acetate (C3H6O2)


1 L 0.2 N Sodium Hydroxide (NaOH)
250 mL 1 N Hydrochloric Acid (HCl)
Distilled Water (H2O)
Ice

2.2 Apparatus

Thermostats at 25 and 35
Fice 250-mL Erlenmeyer Flasks
50-mL pipette
5-mL pipette
Stopwatch or timer

2.3 Methods

A test tube containing 12 ml of methyl acetate was set into a thermostat at 25oC.
Two hundred fifty ml of standardized 1 N HCl is placed in a flask clamped in the
thermostat. After about 10-15 minutes, when thermal equilibrium is established,
several 5-ml aliquots of the acid were titrated with the standard NaOH solution with
phenolphthalein as the indicator. Then 100 ml of the acid was transferred to each of
two 250-ml flasks clamped in a thermostat, and 5 minutes were allotted for the
reestablishment of thermal equilibrium. Precisely 5 ml of methyl acetate was
transferred to one of the flasks using a clean, dry pipette; the timer was started when
the pipette was half emptied. The reaction mixture was shaken to provide thorough
mixing.
Five ml of the aliquot was withdrawn from the flask as soon as possible and
was run into 50 ml distilled water. The solution was chilled in an ice bath and titrated
at once. The time at which the pipette has been half emptied into the water in the
titration flask was recorded together with the titrant volume. Additional samples were
taken at 10-minute intervals for an hour then 20-minute intervals for the next hour and
a half. A second determination was started shortly after the first one to provide a check
experiment.
With the same procedures, two runs were made at a temperature of 35o. Because of the
higher rate of reaction, three samples are first taken at 5-min intervals, then several at
10-min intervals, and a few at 20-min intervals.

2.4 Sketch

ln M vs time
-0.93
0 5 10 15 20 25
-0.94
-0.95
-0.96
ln M

-0.97 y = 0.0001x - 0.9635


R = 0.0021
-0.98
-0.99
-1
Time (min)

Figure 2.4-1. ln M against time at 25


ln M vs time
-0.88
0 5 10 15 20 25
-0.9

-0.92
y = 0.0043x - 0.9832

ln M
-0.94 R = 0.9206
-0.96

-0.98

-1
Time (min)

Figure 2.4-1. ln M against time at 35

3. Results

Rate Constant @ 25oC

Time (minutes) Normality (N) Volume NaOH used (mL) Rate Constant (k)

0 0.37561 9 ---

5 0.384345 6.5 0.1518483866

10 0.38435 8.6 0.1140569568

20 0.410551 8.9 0.06960737125

Average Rate Constant 0.1118375716

Trial Initial Final NaOH M


Aliquot M NaOH ln M
(min) Reading Reading used Solution
0 5 0.8 9.8 9 0.218378 0.393081 -0.93374
5 5 9.8 18.3 8.5 0.218378 0.371243 -0.9909
10 5 18.3 26.9 8.6 0.218378 0.37561 -0.9792
20 5 26.9 35.8 8.9 0.218378 0.388713 -0.94491

Rate Constant at 35oC

Time (minutes) Normality (N) Volume NaOH used (mL) Rate Constant (k)

0 0.393081 8.6 ---

5 0.371243 8.8 0.2070570799

10 0.37561 8.4 0.118979842

20 1.563587 9.4 0.06906049265

Average Rate Constant 0.1316991382

Trial Initial Final NaOH M


Aliquot M NaOH ln M
(min) Reading Reading used Solution
0 5 1.3 9.9 8.6 0.218378 0.37561 -0.9792
5 5 10 18.8 .8.8 0.218378 0.384345 -0.95621
10 5 18.8 27.6 8.8 0.218378 0.384345 -0.95621
20 5 28 37.4 9.4 0.218378 0.410551 -0.89026
4. Discussion

Based on the data shown in the tables above, the results show that as the duration of the
hydrolysis of methyl acetate is proportional to the amount of 0.2N NaOH being used to achieve
the equivalence point. The amount of base used is equivalent to the total amount of acetic acid
formed in the reaction between the base and methyl acetate.

At 35oC, the rate constant calculated was higher than that of 25oC. This is because as the
temperature increases the kinetic energy of the molecules also increase causing them to collide
and therefore increasing the rate of reaction.

In this reaction, HCl was used as a catalyst without changing the concentration of the
solutions. For first-order reactions, the graph of the concentration of the solution vs time would
result with a straight line but in this case, the graph has some slight deviations or curves due to
some human errors made during the experiment.

Arhenius equation describes the influence of temperature. The reaction observed is the
hydrolysis of methyl acetate which produces acetic acid and methanol. From the experiment, it
was observed that as the temperature increases, the rate constant also increases. Comparing the
calculated rate constants with the graphed data, there really is some difference and this might be
due to human errors that were made during the experiment.

5. Conclusion
As the temperature increases the rate constant also increases. Therefore, rate constant is
directly proportional to temperature.

Appendix:
Sample Calculations:
()() 2.303 1
N= K= log(0)
()

5 minutes interval:
(1.27)(16.3) 2.303 16.3
N= (55)
= 0.37561N K= log ( 6.5 )
5

= 0.1518483866 m-1

References

[1] Atkins P. and de Paula J. 2006. Atkins Physical Chemistry. 8th ed. Oxford: Oxford
University Press.

[2] [1] Pauling, L.C. (1988) General Chemistry, Dover Publications

[3] Chemical Engineering Department, CIT-U. (2017). Laboratory Manual for ChE 324.
Cebu.