6th IEEE International Symposium on Applied Computational Intelligence and Informatics • May 19–21, 2011 • Timiúoara, Romania

2 Ethyl-hexanol Output Temperature Control in

Hydrogenation process
R.Both*, C. Festila* , E. Dulf *, T.Szelitzky* and A.O. Neaga*
* Technical University of Cluj-Napoca, Faculty of Automation and Computer Science, Romania (Tel: +40-264-401821;
e-mail: roxana.both@aut.utcluj.ro; clement.festila@aut.utcluj.ro; tibor.szelitsky@aut.utcluj.ro;
adrian.neaga@aut.utcluj.ro)

Abstract—In the petrochemical technological processes, the
synthesis of 2 ethyl-hexanol-oxo-alcohol is of highest
importance, being achieved through catalytic hydrogenation
of 2 ethyl-hexenal. The hydrogenation reaction is highly
exothermic so the reactor output temperature may become
critical. The paper models the complex process of these
chemical reactions and proposes and designs a new control
system structure and a new control algorithm for the
reactor output temperature.
I. INTRODUCTION
One of the most important petrochemical processes is
the industrial scale production of oxo alcohols
(plasticizers alcohols). From these chemical compounds,
2 Ethyl-hexanol (2-EH) represents about 70% of the total
consumption of plasticizers alcohols.
The industrial synthesis of 2 ethyl-hexanol is based on
the hydrogenation of 2 ethyl-hexenal, like (1).
CH3- CH2- CH2- CH= C- CHO + 2 H2
| +H2
CH2-CH3
2 ethyl-hexenal
reaction mixture. Too high temperatures must be avoided
because they may start some “side-reaction” and the
efficiency in the product (2 ethyl-hexanol) decreases. This
also leads to an increase in the power consumption (in
cooling process) and in production costs. The
technological recommended temperature in the
hydrogenation reactor is about 160° C.
In order to sync the reaction heat, an efficient method is
to dilute the 2 ethyl-hexenal with an inert compound. A
proper solution is to use for dilution just the final product:
the recirculated 2 ethyl-hexanol feed.
The input temperature of the reactants needs to be
between 90° C and 110° C in order to start the
hydrogenation reaction. The reference input temperature
of the reactants is given by the catalyst degree of activity,
which decades slowly during the time. Only at the end of
the “catalysts’ life”, in order to use the catalyst to the
maximum, the input temperature will reach 120° C.
A process flow diagram of a typical 2 ethyl-hexenal
hydrogenation process applied in industrial plants is
presented in Fig.1.

CH3-CH2-CH2-CH2-CH-CH2OH
| (1)
CH2-CH3
2 ethyl-hexanol

The 2 ethyl-hexenal catalytic hydrogenation reaction is

possible in gas or in liquid phase. The first case asks for
high energy consumption and great dimensions of the
equipment but with the possibility of catalyst regeneration.
The only drawback of the second case is the impossibility
to regenerate the catalyst but the volumes of catalyst is
lower. That is because the actual paper analyzes the
hydrogenation process in liquid phase.
In order to increase the hydrogenation reaction speed, a
specific catalyst is added. Depending on the catalyst’s
Figure 1. Process flow diagram of a typical 2 ethyl-hexenal
type, the carbonyl group and the double carbon atoms hydrogenation process applied in industrial plants
bound can either both be hydrogenated or only one of
them. For the chosen liquid phase hydrogenation of 2
ethyl-hexenal, Nickel was chosen as catalyst, deposited on II. MATHEMATICAL MODELING
silica support, based on the BASF license, [1],[3].
About 90% of the hydrogenation reaction results in the
first third (superior third) of the reactor and it is highly In order to maintain the internal hydrogenation reactor
exothermic which increases the temperature of the temperature to a desired specific value the method aims to
prevent the reactor overheating by adding a neutral

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R. Both et al. • 2 Ethyl-hexanol Output Temperature Control in Hydrogenation process

compound: through the recirculation of 2 ethyl-hexanol kp

flow, [4]. The total amount of heat produced inside the T f (s) = e − sτ m q( s ) (9)
hydrogenation reactor, taking into consideration the Tp s + 1
dilution with 2 ethyl-hexanol, will be expressed as
follows: ΔT f K
kp = = 0.0448 (10)
Qtotal = Q E − QO
*
(2) ΔQt MJ / h
where: From experimental analysis it was approximated:
QE - is the heat developed by 2 ethyl-hexenal τ m = 800 s and Tp= 2000 s.
hydrogenation reaction; The simulation scheme was implemented in Matlab –
QO* - is the heating decrease due to the 2 ethyl- SIMULINK, based on (2) to (7), and presented in Fig.2.
hexanol recirculated flow (dilution effect).
The heat developed by 2 ethyl-hexenal hydrogenation
process (without taking into consideration the dilution
with 2 ethyl-hexanol), can be expressed as:
*
QE theoretic = k 0* ⋅ FE ⋅ H Et (3)
where:
FE - is the 2 ethyl-hexenal flow;
H Et - specific exothermic heat by synthesis 2 ethyl-
hexenal.
If a linear catalyst deactivation is also taken into
consideration, (3) becomes:
Figure 2. Simulation scheme for temperature evolution inside the
QE ,cat = k 0 ( a 0 − αFE ) FE (4) hydrogenation reactor

where: Į is the deactivation coefficient of the catalyst. As result of the simulation, the evolution of the output
If the dilution with 2 ethyl-hexanol is taken into temperature of the product without 2 ethyl-hexanol
consideration the total amount of heat developed by the dilution, is presented in Fig.3.
hydrogenation reaction is [2]:
250
Qtreal = (c pE FE + c pO FO )(T f − Ti ) (5)
where:
Temperature [deg]

c pE - is the specific heat capacity of 2 ethyl-hexenal;
c pE - is the specific heat capacity of 2 ethyl-hexanol;
FO - is the flow of 2 ethyl-hexanol;
Tf - the output temperature of the product;
Ti - the input temperature of the reactants.
From (2), (4) and (5) the dilution effect of 2 ethyl-
hexanol can be expressed as follows:
* *
QO = Qtreal − QEtheoretic = β ⋅ FO
The dependence between the total amount of heat
produced inside the hydrogenation reactor and the 2 ethyl-
hexenal flow and the 2 ethyl-hexanol recirculated flow is:
Qtotal = k 0 (a 0 − αFE ) FE − β ⋅ FO
The linearized model in steady state operating point is
described by FE0=4.2 m3/h, FO0=27 m3/h, Ti=100°C,
Tf=160°C:
dQtotal dQtotal
ΔQtotal = ΔFE +
dFE FE = FE 0
dFO FO = FO 0
The relationship between the output temperature of the
products and the heat transfer rate can be expressed as
follows [5]:
dT f
+ ϕ ⋅ T f = k ⋅ q (t − τ m )
dt
By applying Laplace transform results:
200
150
100
0 2000 4000 6000 8000 10000
Time [sec]
Figure 3. Output temperature evolution
(5) As previously presented, the maximum admissible
temperature inside the reactor is 160°C. It is clear the
necessity of the 2 ethyl-hexanol recirculation flow.
III. CONTROL STRATEGY DESIGN AND SIMULATION
(6)
In order to maintain the output temperature at the
maximum admissible value, a certain amount of 2 ethyl-
hexanol must be recirculated,[2].
At present time, the solution for 2 ethyl-hexanol
ΔFO (7) recirculated flow control is done with a flow transducer
and a pneumatic valve, which are presented in Fig.1.
The new solution proposed for 2 ethylhexanol
recirculated flow control is based on the replacing of the
pneumatic valve. The variable flow of 2 ethyl-hexanol
may achieved directly by the centrifugal pump P4, whose
rotational speed is changed by induction drive motor,
(8) supplied from an three phase electronic power inverter.
The 2 ethyl-hexanol flow is measured with the old flow
transducer, Fig.1.

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 6th IEEE International Symposium on Applied Computational Intelligence and Informatics • May 19–21, 2011 • Timiúoara, Romania

In order to implement the new control solution for 2
ethyl-hexanol recirculated flow control, the
implementation costs are reduced to the cost of three
phase electronic power inverter.
It was determined experimentally that the flow ratio
between the 2 ethyl-hexenal flow and the recirculated 2
ethyl-hexanol flow must be maintained at a specific value
in order to maintain the output temperature below the
critical value. The value of the flow ratio must be changed
as the catalyst gets older (deactivated). A consequence of
the catalyst deactivation is the decreasing of the output
temperature of the product. At present time, the reference
value for the 2 ethyl-hexanol control loop is set manually,
by an operator, without prior decision on optimal value.
The authors propose a cascade control in order to set
the reference value for the 2 ethyl-hexanol control loop
automatically. This solution can be implemented by using
a temperature transducer in order to measure the output
temperature of the product and a second controller.
The proposed control solution is presented in Fig.4.

Figure 4. Cascade control loop for output temperature control

From this cascade control loop, the minor loop for 2 ethyl- As it can be observed in Fig.6 the new control solution is
hexanol flow control is presented in Fig.5. much faster. The overshoot is higher, but this does not
disturb the process evolution, especially the output
temperature, which is the main parameter. In both cases was
implemented a PI controller with an imposed phase margin
γ k * = 60 .
For the major loop from the cascade, the controller was
designed using the imposed phase margin design method,
Figure 5. The 2 ethyl-hexanol control loop with the same value of phase margin. The obtained controller
is also a PI controller.
For performance analysis of the new control algorithm
Both control structures for 2 ethyl-hexanol flow control
presented in Fig.4, several simulation tests have been carried
(existing and proposed), were implemented and simulated in
out. The result form one experiment, is presented in Fig.7.
Matlab – SIMULINK environment.
Output temperature of 2 ethyl-hexanol [deg]

A comparison between the results obtained with both 160

control structures is presented in Fig.6. 150
2.5 140

2 new control solution 130

2 ethyl-hexanol flow

old control solution

120
1.5
110
1 100

90
0.5 0 0.5 1 1.5 2 2.5
Time [sec] 4
x 10
0 Figure 7. Output temperature evolution
0 50 100 150 200 250 300
Time [sec]
The simulation is done over a period of 25000 sec,
Figure.6. 2 ethyl-hexanol flow evolution equivalent with § 6.9 hours. The imposed set point is 160°C.

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 R. Both et al. • 2 Ethyl-hexanol Output Temperature Control in Hydrogenation process

As it can be observed from Fig.7, the output temperature considered at t=25000 sec. The evolution of the output
reaches the acceptable range after 10000 sec and reaches the temperature is presented in Fig.10
steady state after 20000 sec.
A. Disturbance rejection 180

For disturbance rejection analysis a simulation is done

Output temperature [deg]

over a period of 50000 sec. A step disturbance of +/- 10% is 170
considered in the input value of 2 ethyl-hexenal flow at
t=20000 sec. 160
- 6.25 % Tf *
+ 6.25 % Tf *
The evolution of the output temperature is presented in
Fig. 8.
150
166
140
164 2 3 4 5
Output temperature [deg]

Time [sec] 4
- 10% Fe x 10
162
+ 10% Fe Figure 10. Output temperature evolution

160
158
156
154
2 2.5
Figure 8. Output temperature evolution
It is possible to see that the controlled variable reaches the
set point quickly and that the overshoot is very small <4%. It
is also checked that the manipulated variable shows a
satisfactory behavior and reaches the steady state. The
evolution of the manipulated variable (2 ethyl-hexanol
recirculated flow) is presented in Fig.9.
20
2 ethyl-hexanol recirculated flow
It is possible to see that the controlled variable reaches the
new set point quickly and that the overshoot is very small
<4%.
IV. CONCLUSIONS
3 3.5 4 4.5 5
Time [sec] 4
The paper presents the output temperature control of a 2
x 10 ethyl-hexenal hydrogenation process. The authors developed
a mathematical model for temperature evolution at the output
of the hydrogenation reactor. The developed model was
used to develop a new system structure and control algorithm
for the output temperature control. The control strategy was
implemented and simulated in Matlab-SIMULINK
environment. The control strategy performance was analyzed
in presence of a disturbance in input flow of 2 ethyl-hexenal.
ACKNOWLEDGMENT

This work was supported by the project "Doctoral studies

19 in engineering sciences for developing the knowledge based
society-PRODOC”, contract no. POSDRU/6/1.5/S/5, project
18 +10% Fe
co-funded from European Social Fund through Sectorial
-10% Fe Operational Program Human Resources 2007-2013.
17
REFERENCES
16 [1] W L. Luyben, Process modeling, simulation and control for chemical
engineers, McGraw Publishing Company, 2ed, 1996.
[2] S. Agachi, Automatizare Proceselor Chimice, Casa Cartii de Stiinta,
15 Cluj-Napoca, 1994
2 2.5 3 3.5 4 4.5 5
Time [sec] x 10
4 [3] M.C. Rezende, A.C. Costa and R.M.Filho, “Control and optimization
Figure 9. Manipulated variable evolution of a three phase industrial hydrogenation reactor”, International
Journal of Chemical reactor engineering, vol.2, 2004
B. Setpoint tracking [4] R.Both, C.Festila, E.H.Dulf and A.O.Neaga, “Modeling and
simulation of the liquid phase 2-ethyl-hexenal hydrogenation”, AQTR
Proceedings, Cluj Napoca, 2010
For a set point tracking analysis a simulation is done over [5] F.P. Incropera, D.P. DeWitt, T.L. Bergman and A.S. Lavine,
a period of 50000 sec. A set point variation of +/- 6.25 % is Fundamentals of Heat and Mass Transfer, 6th Ed., Wiley, 2007

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