Iraqi Journal of Chemical and Petroleum Engineering 

 Vol.17 No.1 (March 2016) 99- 108 

ISSN: 1997-4884 

 
 
 
 

 

Study in Kinetics of Saponification Reaction of Diethyl Adipate with 

Sodium Hydroxide Solution under Reactive Distillation 
 

Raghad fareed kasim* and rouaa ali shokorr** 

College of engineering-University of Baghdad 

*email:rfkalm@yahoo.com 

** email:hu.iraq91@gmail.com 

 

Abstract 

   This research presents a new study in kinetics under reactive distillation by using 

consecutive two – step reaction : the saponification reaction of diethyl adipate with 

sodium hydroxide solution . The distillation process takes the role of withdrawing the 

intermediate product (sodium monoethyladipate SMA) which otherwise converts to 

the final product of low purity.The effect of three parameters were studied through a 

design of experiments applying 2
3
 factorial design. These parameters were : the mole 

ratio of DA to NaOH solution (0.1 and 1) , NaOH solution concentration (3 N and 8 

N) , and batch time (1.5 hr. and 3.5 hr.) . The conversion of DA to sodium 

monoethyladipate(SMA)(intermediate product) was the effect of these parameters 

which was detected .The results showed that increasing mole ratio of DA to 

NaOHsolution increases the conversionto a maximum value within the range of 

study.The effect of NaOH solution concentration decreases the conversion to a 

specified value within the range of study . The effect of batch time on conversion was 

decreasing the conversion to a specified value within the range of study . The 

maximum attainable conversion within the studied range of parameters was  eighteen 

fold of thebase case.Reaction rate constant k and the order of reaction n of first 

reaction weredetrminedusing the differential method . The study attempted to 

determine n and k under the maximum conversion condition obtained in this system 

which corresponds to : feed mole ratio of diethyl adipateDA to NaOH solution of 

0.3,NaOH solution concentration of3 Nandtime of1.5 hr.The study showed that the 

reaction order was 1.5and reaction rate constant was 0.8m
3
/kmol.s at a temperature of 

100     
 

Key Words: reactive distillation, kinetic study, consecutive reaction, saponification 

reaction. 
  

Introduction 

   Separation is one of the most 

significant processes in chemical 

engineering. From ancient times to 

recent days, separation processes have 

been implemented in almost every 

chemical process. The distillation 

process is the most suitable separation 

process in the chemical and petroleum 

industries. Reactors are also essential 

parts of any chemical industry. Reactor 

effluents do not usually meet the 

Iraqi Journal of Chemical and 
Petroleum Engineering 

 

University of Baghdad 
College of Engineering 



Study in Kinetics of Saponification Reaction of Diethyl Adipate with Sodium Hydroxide Solution under 

Reactive Distillation 
 

100                                     IJCPE Vol.17 No.1 (March 2016)             -Available online at: www.iasj.net 
 

specification criteria due to the process 

of the unconverted materials.    

   Therefore, it is quite common in 

industry to see reactors followed by a 

separation section with recycles. From 

this point of view, it is important to 

study and investigate the reactor  

/ Separation / recycle system. One 

aspect of studying this system is the 

reactor combined with the separation 

unit. This is referred to as reactive 

distillation [1]. It involves 
simultaneous chemical reaction and 

distillation [2]. RD has been used in 

industry from many decades, but its 

area of application has grown 

essentially in the past decade [3]. 

There are many documented success 

references involving the industrial 

implementations of RD. The 

implementations of RD in the 

petroleum and chemical industries 

have been increased quickly in the past 

decade. One such example is the 

production of methyl acetate by the 

Eastman plant. In this case a single RD 

column replaced the conventional flow 

sheet consisting of eleven major 

operation units with an assortment of 

pumps, heat exchangers, and 

controllers. The result was a five-

doubles reduction in energy 

consumption and capital investment 

over the conventional design for 

methyl acetate production [4]. 

   For esterification reactions: when 

carboxylic acid treated with an alcohol, 

an ester is formed. Saponification 

reaction is a kind of esterification 

reaction that can be conducted under 

reactive distillation (RD). The general 

utility of RD is increasing the 

conversion of reversible reactions [5]. 

RD depends on the withdrawal of the 

product (or one of the products) by 

evaporation from the reacting mixture. 

This technique accelerates the forward 

reaction .In previous research of the 

investigators [6], it was shown that the 

maximum conversion obtained for this 

system was 18.58fold of that for the 

base case (the base case is the 

experiment that carried out at lower 

values of all the parameters, which is 

regarded as base or reference case). 

   The maximum conversion value 

corresponded to the set of parameters 

(under study): feed mole ratio of DA to 

NaOH solution (x1) = 0.3, 

NaOHsolution concentration (x2) = 3 

N, and distillation time (x3) = 1.5 h.   

   Newberger and Kadlec [7], studied 

the kinetic of saponification reaction of 

diethyl adipate with sodium hydroxide 

solution in a batch isothermal system 

at temperature of 293.1 K. They 

determined reaction order and reaction 

rate constant for the two consecutive 

reactions which can be represented as 

follows: 

 

(CH2)4(COOC2H5)2+NaOH
  
⇒(CH2)4(C

OONa)(COO C2H5) + C2H5OH   ... (1) 

 

(CH2)4(COONa)(COOC2H5)+NaOH
  
⇒

(CH2)4(COO Na)2 + C2H5OH      ... (2) 

 

   They found that the rate constant of 

the first reaction (k1) to be 9.3 m
3
 / 

kmole . s , while that of the second 

reaction (k2) to be 7.7 m
3
 /      kmole . s 

. These values were obtained at 

temperature 293.1  K . It is obvious 

that k1> k2 i.e. the first reaction is 

faster than the second. 

   They also found that the frequency 

factors of Arrhenius equation , and the 

activation energies of the two reactions 

were: 

a1 = 4.87 * 10
6
 m

3
 / kmole . s      

a2 = 3.49 * 10
6
 m

3
 / kmole . s                    

E1 = 42.2 kJ / mole 

E2 = 25.0 kJ / mole 

 

   It is obvious that E1> E2 , so the first 

reaction has a higher energy barrier 

than the second reaction. 

 

 



Raghad fareed kasim and rouaa ali shokorr 

 

-Available online at: www.iasj.net                  IJCPE Vol.17 No.1 (March 2016)                                101 
 

   In addition , they determined the 

heats of the two reactions to be: 

 

ΔH1 = - 45.2 ± 3.4 kJ / mole  

ΔH2 = - 68.0 ± 4.2 kJ / mole 

 

   These quantities were found to 

contribute at most 0.5 K in temperature 

rising in tubular reactor which they 

used. 

 

Table 1, The reaction order and reaction rate constant values for diethyl adipate with 

sodium hydroxide solution at (293.1 K) temperature [8] 

Investig-ator CA kmol. /m
3
 CB kmol. /m

3
 

 

Reaction 

order 

k1 , m
3
/ 

Kmol.s 

k2 , m
3
/ 

kmol.s 

Ingold 

(1931) 
0.002 0.002 2 3.52 0.704 

Westhe-imer 

(1942) 
0.01 0.01 2 5.20 1.83 

Westhe-imer 

(1942) 
0.005 –0.011 0.005–0.011 2 5.7 – 6.1 ----- 

Frost and 

Schwe-mer 

(1952) 

0.01 0.01 – 0.02 2 ----- 1.7 – 2.2 

Newber-ger 

and Kadlec 

(1973) 

0.02 0.05 2 9.3 7.7 

   They also compared their results 

with some former ones that were 

published as given in Table (1). 

   The reaction system can be 

represented by: 

A + B   C + D 
C + B   E + D 
Where: 

A: refers to diethyl adipate (DA) 

B: refers to sodium hydroxide solution 

C: refers to sodium monoethy ladipate 

(SMA) 

D:  refers to ethanol 

E: refers to disodium adipate (DSA) 

 

   From Eq. (1), the kinetic study of the 

first reaction depended on measuring 

SMA concentration (i.e. CC). 

 

rC = 
   

  
 = k CA CB                       … (3) 

 

Eq. (3) represents the rate equation. 

 

   In order to apply the differential 

method rA must be determined. From 

Eq. (4) we see that rC can be converted 

to rA. 

 
  

                
=

   

                
     … (4)  

 

   As the stoichiometric number of C 

and A is the same, therefore; -rA=rC 

numerically. So rA can be determined 

directly from calculating rC as shown 

later. 

 

Experimental Work 

 

1- Materials 
   Diethyl adipate, sodium hydroxide 

pellets. Hydrochloric acid HCl ,borax , 

methyl red , methyl orange for sodium 

hydroxide solution standardisation. 

 

 



Study in Kinetics of Saponification Reaction of Diethyl Adipate with Sodium Hydroxide Solution under 

Reactive Distillation 
 

102                                     IJCPE Vol.17 No.1 (March 2016)             -Available online at: www.iasj.net 
 

2- Procedure 
1- According to the design of 

experiment Table (2) 

,(Montgomery[9]) three factors 

were intended to study (feed mole 

ratio , sodium hydroxide (NaOH) 

solution concentration, and batch 

"distillation" time) within the ranges 

set in the Table(3). 

2- Sodium hydroxide (NaOH) solution 
with (3N concentration), was 

prepared and standardized using 

indicators, (Vogel [10]) and pH-

meter. 

3- Measured amounts (12 – 129 ml.) of 
diethyl adipate (DA) and sodium 

hydroxide "NaOH" solution (31 – 

332 ml.) was mixed in (500 – ml.) 

distillation flask which was 

shielded. 

4- Heating the mixture till boiling. The 
distillate began to appear at 

approximately about 100 
0
C. 

5- The distillate was collected in 
receiving conical flask. It was 

noticed that it was composed of two 

layers. 

6- The distillate was transferred to a 
(500 - ml.) separating   funnel. 

7- The weight and volume of each 
layer were measured. 

8- Relative conversions were also 
determined for the center values of 

the parameters shown in Table 

(3).Additional experiments were 

performed to get sufficient data for 

plotting. 

 

3- Test Method 
   FTIR measurement was done for 

each layer which showed that sodium 

monoethyladipate (SMA) appeared in 

the dominate upper layer. The 

unreacted diethyl adipate (DA) 

appeared in the impaired lower layer. 

   Atomic absorption was made for the 

upper layer to measure the 

concentration of SMA (CC)as given in 

Table (4). 

 

Table 2, Design of experiments 

Time(x3),

(hr) 

NaOH 

solution 

concentration 

(x2) , (N) 

Feed mole 

ratio (x1) , 

(mol. DA / 

mol. NaOH) 

1.5 3 0.1 

1.5 3 1 

1.5 8 0.1 

1.5 8 1 

3.5 3 0.1 

3.5 3 1 

3.5 8 0.1 

3.5 8 1 

 

Table 3, Ranges of parameters studied 

Factor 

Low 

value 

(-) 

Centre 

value 

(0) 

High 

value 

(+) 

Feed mole ratio 

(x1) , (mole DA 

/ mole NaOH 

solution) 

0.1 0.55 1 

NaOH solution 

concentration  

(x2) , (N) 

3 5.5 8 

Time (x3) , (h) 1.5 
2.5 

 

3.5 

 

 

Results and Discussion 

   From SMA concentration, relative 

conversion (conversion of DA to SMA 

relative to base case conversion) was 

calculated. The variation of relative 

conversion with feed mole ratio x1 

were drawn for NaOH solution 

concentration x2 = 3 N , and different 

batch time x3 = 1.5 and 3.5 h as shown 

in Fig. (1).From this figure , it is 

obvious that for the two curves the 

relative conversion proportionally 

increased with increasing feed mole 

ratio in the range x1 = (0.1 - 0.3) . The 

two curves have a maximum relative 

conversion at x1 = 0.3 which seems to 

be the best value in our range of feed 

mole ratios. After that increasing, feed 

mole ratio in the rangex1 = (0.3 – 1) 

decreased relative conversion. The 

increasing in relative conversion with 

increasing feed mole ratio in the 

rangex1 = (0.1 – 0.3) was because of 

the increasing in SMA concentration in 

this range of feed mole ratios.  



Raghad fareed kasim and rouaa ali shokorr 

 

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   The decreasing in relative conversion 

for the rangex1 = (0.3 – 1) was due to 

the decreasing in SMA concentration.    

   This can be explained as follows: the 

rate of first conversion reaction (SMA 

production) is higher than the rate of 

second conversion reaction (SMA 

consumption), Newberger and Kadlec 

[7]. The increasing in feed mole ratio 

in the range (x1 = 0.1 – 0.3) activated 

the first conversion reaction (i.e SMA 

production increased) and its 

concentration in distillate increased. 

Higher increasing in feed mole ratio in 

the range (x1 = 0.3 – 1) activated the 

second conversion reaction (i.e. SMA 

consumption increased) so its 

concentration in distillate decreased. 

   Also, it is clear from this figure that 

the relative conversion for the curve of 

shorter distillation time (t = 1.5 hr.) at 

(x1 = 0.15 – about 0.8) was higher than 

that of longer distillation time (t = 3.5 

hr.). At (x1 = 0.3) relative conversion 

for the curve of shorter distillation time 

was (18.58), while for the curve of 

longer distillation time was (9.76). Fig. 

2 also explains the variation of relative 

conversion with feed mole ratio (x1) 

and different batch time (x3 = 1.5 and 

3.5 hr.). The two curves were drawn 

for the same NaOH solution 

concentration (x2 = 8 N).  

   From this figure, it is clear that for 

the curve of shorter distillation time, 

relative conversion increased with feed 

mole ratios in the range (x1 = 0.1 - 

0.3).  

   The curve has a maximum value of 

relative conversion (2.76) at (x1 = 0.3). 

After that the relative conversion 

decreased when feed mole ratio 

increased in the range (x1 = 0.3 – 1). 

   The peak of the curve of shorter 

distillation time (2.76) is lower than 

the corresponding one of Fig. 1.This is 

because of lower weight of distillate 

upper layer and higher volume of DA 

.Relative conversion is a function of 

SMA concentration, weight of 

distillate upper layer, and DA volume 

as shown in Eq. (5): 

 

Relativeconv.=
                   

        (    )          
... (5) 

 

   For the curve of longer distillation 

time it is clear that the relative 

conversion decreased when feed mole 

ratio increased in the range (x1 = 0.1 - 

0.55).  

   The curve has a minimum value of 

relative conversion (0.18) at (x1 = 

0.55). Then relative conversion 

increased somewhat till (x1 = 1).  

   The decreasing in relative conversion 

with feed mole ratio in the range (x1 = 

0.1 – 0.55) because of decreasing in 

weight of distillate upper layer and 

increasing in DA volume. The 

increasing in relative conversion in the 

range (x1 = 0.55 - 1) was because of 

increasing in weight of upper layer 

distillate and increasing SMA 

concentration.  

   The peak of the curve of longer 

distillation time (0.62) is lower than 

the corresponding one of Fig. 1.This is 

because of lower weight of distillate 

upper layer and higher volume of DA 

as mentioned above. 

   Fig. 3 shows the variation of relative 

conversion with NaOH solution 

concentration (x2). The curve was 

drawn for feed mole ratio (x1 = 0.3) 

and batch time (x3 = 2.5 hr.). From this 

figure, it is clear that the relative 

conversion decreased with increasing 

NaOH solution concentration in the 

range (x2 = 3 – 5.5 N) . The curve has a 

minimum value of relative conversion 

(0.39) at (x2 = 5.5 N) . After that the 

relative conversion increased when 

NaOH solution concentration increased 

in the range (x2 = 5.5 – 8 N) . The 

behaviour of this curve was due to the 

decreasing then increasing of SMA 

concentration with NaOH solution 

concentration. 

 

 



Study in Kinetics of Saponification Reaction of Diethyl Adipate with Sodium Hydroxide Solution under 

Reactive Distillation 
 

104                                     IJCPE Vol.17 No.1 (March 2016)             -Available online at: www.iasj.net 
 

   Fig. 4 explains the variation of 

relative conversion with distillation 

time (x3). The curve was drawn for 

feed mole ratio (x1 = 0.3) and NaOH 

solution concentration (x2 = 3 N). 

From this figure, it is clear that the 

relative conversion decreased when 

distillation time increased in the range 

(t = 1.5 – 2.5 hr.).  

   The curve has a minimum value of 

relative conversion (0.68) at (t = 2.5 

hr.)  . After that, the relative 

conversion increased with increasing 

distillation time in the range (t = 2.5 – 

3.5 hr.). This behaviour is due to the 

decreasing then increasing of SMA 

concentration with distillation time. 

   Fig. 5 also explains the variation of 

relative conversion with distillation 

time (x3), and feed mole ratio (x1 = 

0.3). The curve was drawn for NaOH 

solution concentration (x2 = 8N).  

   From this figure, it is clear that the 

relative conversion decreased with 

increasing distillation time. This can be 

attributed to the decreasing in SMA 

concentration as discussed before. 

 

 

Fig. 1, Relative conversion vs. feed 

mole ratio (x1) for NaOH sol. conc. = 3 

N and t = (1.5 & 3.5 hr.). 

 

 

 

Fig. 2, Relative conversion vs. feed 

mole ratio (x1) for NaOH sol. conc. = 8 

N and t = (1.5 & 3.5 hr.). 

 

 

 

Fig. 3, Relative conversion vs. NaOH 

solution concentration (x2), (N) for 

feed mole ratio = 0.3 and t = 2.5 hr. 

 

 

 

 

 



Raghad fareed kasim and rouaa ali shokorr 

 

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Fig. 4, Relative conversion vs. t (x3), 

(hr.) for feed mole ratio = 0.3 and 

NaOH sol. conc. = 3 N. 

 

 

Fig. 5, Relative conversion vs. t (x3), 

(hr.) for feed mole ratio = 0.3 and 

NaOH sol. conc. = 8N. 

 

   

 

 

 

 Table 4, shows SMA concentration in 

distillate upper layer with distillation 

time for the maximum - conversion set 

of parameters (i.e. Feed mole ratio = 

0.3 and NaOH sol. conc. = 3 N). 

t , hr. CC , ppm. 

0 0 

1.5 106.10 

2.5 10.55 

3.5 50.31 

 

 
Fig. 6, SMA concentration in distillate 

(ppm.) versus time(hr.) for feed mole 

ratio=0.3 and NaOHsol. Conc. =3N . 

 

Table 5, shows values of diethyl 

adipate concentration (limiting 

reactant) (CA), and reaction rate (-rA) 

with their logarithms. 

Cc , 

ppm 

CA , 

ppm 

Log 

CA 

-rA= 

dCC/dt

= rC 

Log 

-rA 

0 0 ----- ----- ----- 

2.01 2.07 0.32 4.14 0.62 

4 4.13 0.62 4.51 0.65 

106.10 109.48 ----- ----- ----- 

10.55 10.89 1.04 56 1.75 

50.31 51.91 1.72 100 2 

 



Study in Kinetics of Saponification Reaction of Diethyl Adipate with Sodium Hydroxide Solution under 

Reactive Distillation 
 

106                                     IJCPE Vol.17 No.1 (March 2016)             -Available online at: www.iasj.net 
 

 

Fig. 7, Plot of log(-rA) vs log(CA) for 

determining reaction order (n) and rate 

constant (k). 

 

   SMA concentration (Cc) versus 

batch time (t) data was plotted as 

shown in Fig. (6) .The slopes of the 

curve at different values of CC were 

determined .These slopes represented 

the rate of reaction rC which are listed 

in Table (5).From Eq. (6) diethyl 

adipate concentration (CA) was 

calculated from sodium 

monoethyladipate concentration (CC). 

 

CA=CC*
                   (      )

                    (   )
... (6) 

 

   The results are shown in Table (5). 

Also in Table (5) the logarithms of 

these values were obtained. Fig, (7) 

shows a plot of log(-rA) versus log CA.     

   A linear relation was obtained. The 

slope of this relationship represents n 

(order of reaction) and the intercept 

representslog (k) Levenspiel [11].    

   From Eq. (7) and Eq. (8) the 

resulting values of n and k are 1.5 and 

0.8 m
3
/kmole. s respectively.                                                     

 

  
       

     
                                 … (7) 

 

Log k = -0.1 k=0.8 m
3
/kmole.s … (8) 

 

    

   Reaction rate constant (k) for 

saponification of diethyl adipate as 

calculated by Newberger and Kadlec 

(1973) was (9.3 m
3
/kmole.s) at 

temperature of (293.1 K) and initial 

concentrations of DA and NaOH 

solution of (0.02 and 0.05) respectively 

as given in Table (1). 

   In this study reaction rate constant 

was (0.8 m3/kmole.s) at temperature 

about (100 ) (the distillation 
temperature). This was in fair 

agreement with Arrhenius equation Eq. 

[9] which shows that the rate constant 

is inversely proportional with 

temperature. 

 

k = aexp(
  

  
)                                ...  (9) 

 

Or in logarithmic form: 

 

  ( )    ( )  (
 

  
) 

It is obvious that:      ( )  
 

 
 

 

   So increasing temperature till boiling 

is essential to achieve reactive 

distillate, but this technique will retard 

the magnitude of the reaction  - rate (k) 

for this reaction . This issue is a matter 

of balancing between the rate of 

reaction and gaining of a valuable 

intermediate product. 

 

Conclusions 

   From this study the following items 

can be concluded: 

1- Feed mole ratio x1 obviously 
affected the concentration of SMA 

in the distillate. Accordingly the 

conversion was influenced by it. 

Increasing feed mole ratio caused 

increasing in the concentration of 

SMA, and conversion of DA to 

SMA in the range (0.1 - 0.3) , when 

the other factors x2 (NaOH solution 

concentration) and x3 (batch time) 

were fixed at specified values . In 

the range (0.3 –1)of x1 the 



Raghad fareed kasim and rouaa ali shokorr 

 

-Available online at: www.iasj.net                  IJCPE Vol.17 No.1 (March 2016)                                107 
 

concentration , and conversion 

decreased. 

2- Increasing sodium hydroxide 
solution concentration x2 increased 

the conversion with other 

parameters x1 and x3 fixed. That was 

attributed to the effect of NaOH as a 

reactant which accelerated the 

reactions with increasing in its 

concentration. Although, there were 

some ranges x2 = (3 – 5.5 N) of 

NaOH solution concentration which 

caused decreasing in SMA 

concentration, and conversion. 

3- The conversion of DA to SMA for 
x1 = 0.3 and x2 = 3 N showed 

decreasing with increasing batch 

time x3 till x3 = 2.5 h . Then the 

conversion increased with 

increasing x3. 

4- The conversion of DA to SMA for 
x1 = 0.3 and x2 = 8 N showed 

decreasing with increasing batch 

time x3. 

5- The maximum conversion obtained 
in this study was 18.58 fold of that 

for the base case.The maximum 

conversion corresponds to the set of 

parameters (x1 = 0.3, x2 = 3 Nandx3 

= 1.5 h). 

6- The order of reaction and reaction 
rate constant at maximum 

conversion set of parameters were 

1.5 and 0.8m
3
/kmole.s, respectively. 

7- Reaction rate constant determined in 
reactive distillation system is of 

lower value than that with ordinary 

operated system. This affirms 

Arrhenius equation outputs. 

 

Abbreviation 

RD= Reactive Distillation 

DA= Diethyl Adipate 

SMA= Sodium MonoethylAdipate 

DSA= Di-Sodium Adipate 

 

 

 

 

 

Nomenclature 
a= Pre-exponential (frequency) 

factor (m
3
/kmole.s) 

R=  Perfect gas law constant 

(J/mole.K) 

E= Activation energy (kJ/mole) 

CA= Concentration of DA 

(kmole/m
3
) 

CB= Concentration of NaOH soln. 

(kmole/m
3
) 

 

References 

1- Al – Arfaj , M. , " Quantitative 
heuristic design of reactive 

distillation " , Chemical department 

, College of Engineering , 

University of Lehigh , 1999 . 

2- Lone , S. R. , and Ahmad , S. A. , 
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Acetate Reactive Distillation Using 

Aspen Plus" , International Journal 

of Scientific & Engineering 

Research ,   Vol. 3 , No. 8 , PP. (1 – 

5) , 2012 . 

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–Product Reactive Distillation 

Column " , Industrial Chemical 

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(2015) , " Semi- Batch Reactive 

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Adipate with Sodium Hydroxide 

Solution " , Baghdad University, 

Chemical Engineering , 1-133. 



Study in Kinetics of Saponification Reaction of Diethyl Adipate with Sodium Hydroxide Solution under 

Reactive Distillation 
 

108                                     IJCPE Vol.17 No.1 (March 2016)             -Available online at: www.iasj.net 
 

7- Newberger , M. R. , and Kadlec , R. 
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