InGenio Journal
Revista de Ciencias de la Ingeniería de la Universidad Técnica Estatal de Quevedo
https://revistas.uteq.edu.ec/index.php/ingenio
e-ISSN: 2697-3642 - CC BY-NC-SA 4.0
Simulation of an allyl chloride production process
via the propylene chlorination route in ChemCAD
®
simulator
(Simulación de un proceso de producción de cloruro de alilo mediante la
ruta de cloración del propileno en el simulador ChemCAD
®
)
Amaury Pérez Sánchez
1
, Arlette de la Caridad González Abad
1
, Amanda Acosta Solares
2
,
Arlenis Cristina Alfaro Martínez
3
InGenio Journal
Revista de Ciencias de la Ingeniería de la Universidad Técnica Estatal de Quevedo
https://revistas.uteq.edu.ec/index.php/ingenio
e-ISSN: 2697-3642 CC BY-NC-SA 4.0
Volumen 8 | Número 1 | Pp. 1–4 | Enero 2025 Recibido (Received): 2022/mm/dd
DOI: https://doi.org/
10.18779/ingenio.v8i1.970 Aceptado (Accepted): 2024/12/23
Simulation of an allyl chloride production process via
the propylene chlorination route in ChemCAD
simulator
(Simulación de un proceso de producción de cloruro de alilo mediante la
ruta de cloración del propileno en el simulador ChemCAD
)
Amaury Pérez Sánchez
1
, Arlette de la Caridad González Abad
1
,
Amanda Acosta Solares
2
, Arlenis Cristina Alfaro Martínez
3
1
Universidad de Camagüey, Camagüey, Cuba
2
Universidad Central de Las Villas, Santa Clara, Cuba
3
Centro de Ingeniería Genética y Biotecnología de Camagüey, Camagüey, Cuba
amaury.perez84@gmail.com, arlette.delacaridad@reduc.edu.cu, aacosta@uclv.cu,
arlenis.alfaro@cigb.edu.cu
Abstract: Allyl chloride is typically used to make intermediates for downstream
derivatives such as resins and polymers, and in the production of epichlorohydrin. The
present work describes the simulation and conceptual design of an allyl chloride production
process via the propylene chlorination route in ChemCAD
simulator, to know the mass
and energy balances of the intermediate and final streams, the operating and design
parameters of some equipment, and other results of interest. The production process
consists of a fired heater, a fluidized bed reactor, a waste heat boiler, six shell and tube heat
exchangers, two compressors, a gas-liquid absorber and four distillation columns. About
1.336,307 kg/h of allyl chloride are produced at the distillate of the last distillation column
with a purity of 99,92 %, while pure propylene, 2-chloropropene and an aqueous solution
of HCl 32,4 wt. % are also obtained as byproducts. A first-of-its-kind simulation model was
obtained in ChemCAD
, which could be employed for further optimization studies and
productivity increment analysis.
Keywords: Allyl chloride, propylene chlorination, ChemCAD
, simulation, conceptual
design.
Resumen: El cloruro de alilo es típicamente usado para producir intermediarios para
derivativos tales como resinas y polímeros, y en la producción de epiclorohidrina. El
presente trabajo describe la simulación y diseño conceptual de un proceso de producción de
cloruro de alilo mediante la ruta de cloración del propileno en el simulador ChemCAD
,
para conocer los balances de masa y energía de las corrientes intermedias y finales, los
parámetros de operación y diseño de algunos equipos, y otros resultados de interés. El
proceso de producción consiste en un calentador quemador, un reactor de lecho fluidizado,
una caldera de calor residual, seis intercambiadores de calor de tubo y coraza, dos
compresores, un absorbedor gas-líquido y cuatro columnas de destilación. Alrededor de 1
336,307 kg/h de cloruro de alilo son producidos en el destilado de la última columna de
destilación con una pureza de 99,92 %, mientras que también se obtienen como
subproductos propileno puro, 2-cloropropeno y una solución acuosa de HCl al 32,4 % m/m.
Se obtuvo un modelo de simulación primero de su tipo en ChemCAD
, el cual puede ser
empleado para posteriores estudios de optimización y análisis de incremento de la
productividad.
Palabras clave: Cloruro de alilo, cloración del propileno, ChemCAD
, simulación, diseño
conceptual.
Volumen 8 | Número 1 | Pp. 156–173 | Enero 2025
DOI: https://doi.org/10.18779/ingenio.v8i1.970
Recibido (Received): 2024/08/12
Aceptado (Accepted): 2024/12/23
InGenio Journal, 8(1), 156–173 157
InGenio Journal, 8(1), 1–4
| 2
1. INTRODUCTION
Allyl chloride (3-C
3
H
5
Cl) is an important organic intermediate and is mainly used for
producing epichlorohydrin, glycerin, and allyl alcohol, where in industry more than 80 % of
epichlorohydrin is made from allyl chloride [1]. Additionally, allyl chloride is a common
alkylating agent relevant in the manufacture of pharmaceuticals and pesticides. The uses and
applications of allyl chloride may vary according to the product grade. The main form of allyl
chloride is commercial grade, with 99 wt. % minimum purity [2].
Currently, the production routes of allyl chloride generally include:
1) High-temperature propylene chlorination (HTPC) and
2) oxychlorination of propylene (OP).
The investment cost of HTPC is comparatively less because no catalyst is needed, while the
OP process needs the precious metal catalyst, which can easily lose activity. Consequently,
HTPC is generally used in industry [1].
According to [2], while the main commercial production pathway for allyl chloride is the
direct high-temperature chlorination of propylene, while examples of other pathways include:
1) Thermal dehydrochlorination (cracking) of dichloropropane and
2) Oxychlorination using hydrogen chloride and propylene.
However, such processes are either less used or of no commercial interest due to low allyl
chloride selectivity and the generation of byproducts with no significant marketable use.
Some authors have studied the allyl chloride production process via propylene chlorination.
In this case, in [3] a combined environmental and economic evaluation of an allyl chloride
production process via propylene chlorination was performed for a base design and two
alternative designs. The environmental analysis was completed using the waste reduction
(WAR) algorithm, while the economic analysis was accomplished using the commercial
software ICARUS Process Evaluator. All three process options were designed to maintain the
process specifications:
1) The allyl chloride product stream must have a minimum purity of 99,9 mol%,
2) The HCl product stream must be 31,5 wt.%,
3) The 2-chloropropene byproduct stream must have a minimum purity of 95 mol%, and
4) The 2,3-dichloropropene byproduct stream must have a minimum purity of 95 mol%.
Also, [4] used the Integrated Dynamic Decision Analysis (IDDA) approach for reviewing
the design of a plant for the production of allyl chloride by chlorination of propylene under
exothermic conditions, with the objective of building an objective and documented reference for
the decision making about the design alternatives to be adopted for risk minimization.
Likewise, in [2] an allyl chloride production process from propylene and chlorine was
described, comprising three major sections: (1) chlorination; (2) propylene recovery; and (3)
product treatment.
Similarly, in [5] an allyl chloride production process via high temperature chlorination of
propylene was studied and rigorous simulated in Aspen Plus and using dividing wall columns in
the separation section.
Finally, in [6] an allyl chloride manufacturing process via propylene chlorination was
simulated using Aspen Plus simulator, to demonstrate a methodology developed to optimize
processes for sustainability by applying information from the sustainability evaluator and the
Oklahoma State University, as well as to convert the multiobjective optimization problem of
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| 3
sustainability into a single objective problem by using the constraints and the weighted
methods.
Nevertheless, to the best of the authors’ knowledge, an allyl chloride production process via
propylene chlorination has not yet been simulated in ChemCAD
simulator.
Certain chemical company is interested in erecting an allyl chloride production plant via the
propylene chlorination route due to the availability of economic resources, raw materials and a
guaranteed market for this chemical. Consequently, it is necessary and required to carry out the
conceptual design of such a plant to obtain information about its productivity, throughput and
equipment operating parameters, as a first step in the development of this chemical process.
In this context, in the present study an allyl chloride production process via the propylene
chlorination route was simulated for the first time in ChemCAD
simulator v7.1.2, to know the
mass and energy balances of the intermediate and final streams, the operating and design
parameters of the main equipment, as well as the required flowrate of utilities and the heat
curves in all the shell and tube heat exchangers.
2. MATERIALS AND METHODS
2.1. Physical-chemical properties of allyl chloride
As reported by [7] [8], allyl chloride presents the main physical-chemical properties shown
in Table 1.
Table 1. Main physical-chemical properties of allyl chloride.
Property
Value
Units
Other name
3-chloropene
Molecular weight
76,53
g/mol
Freezing point
-134,5
ºC
Boiling point at 101.3 kPa
45,1
ºC
Fire point
4
ºC
Flash point
4
ºC
Specific gravity at 20/4 ºC
0,938
-
Liquid density at 25 ºC
931
kg/m
3
Critical temperature
240,7
ºC
Critical pressure
4.710
kPa
Heat of combustion
24,8
kJ/g
Heat of vaporization at 20 ºC
357
J/g
Specific heat, liquid, at 20 ºC
1,32
J/g.ºC
Solubility at 20 ºC, in water
0,33
%
Viscosity at 25 ºC
0,3136
cP
Refractive index at 15 ºC
1,4153
-
2.2. Description of the allyl chloride production process
Firstly, 3.190 kg/h of gaseous propylene at a temperature and pressure of 25 ºC and 11,7 bar
are sent to a pressure reduction valve to reduce its pressure to 3,58 bar, thus decreasing its
temperature to 10,1 ºC. This cold propylene stream is then sent to a fired heater (Fired Heater) to
increase its temperature to 548 ºC, and the subsequent heated stream is mixed in a mixing nozzle
with 1,400 kg/h of a gaseous chlorine stream at a temperature and pressure of 25 ºC and 6,44 bar,
respectively. The resulting mixed gaseous stream, which has a temperature of 510-515 ºC and a
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| 4
pressure of 3-3,5 bar, is fed to a fluidized bed reactor (Reactor) operating in the temperature and
pressure range of 511-525 ºC and 3,04-4,50 bar, respectively. According to [9], during the thermal
chlorination process, some amounts of carbon can be produced, which has the propensity to
deposit on equipment that operates at temperatures greater than 400 ºC. For this reason, the reactor
chosen for this production process is a fluidized bed with sand (inert solid) on the reaction side. In
this case, the sand provide a large surface area on which the carbon can deposit, acts as a scouring
agent on the immersed heat transfer tubes in the reactor and prevents the buildup of carbon on the
heat transfer surfaces. The carbon deposited preferentially on the sand is removed by combustion
in a solid regeneration unit attached to the reactor, while the regenerated sand is sent back to the
reactor, thus maintaining a constant inventory of solids inside the reactor.
The chlorination reactions are exothermic (Table 2), thus the heat produced by these
reactions is removed using the commercially available heat transfer medium (or coolant)
Dowtherm A
. The hot gaseous crude allyl chloride stream coming from the fluidized bed
reactor at a temperature and pressure of 510-515 ºC and 2,5-3,0 bar, which contains unreacted
propylene along with the reaction products, is sent to a waste-heat boiler (Waste-Heat Boiler)
which utilizes the heat content of this stream to generate low pressure saturated steam (162 ºC
and 6 bar). The outlet cooled gaseous stream of the waste-heat boiler, at a temperature of 200
ºC, is then sent to a shell and tube heat exchanger (Cooler 1) to reduce its temperature to 50 ºC
against cooling water at 30 ºC, and then to another shell and tube heat exchanger (Cooler 2) to
be cooled to -50 ºC against propylene at -62 ºC. The cooled liquid mixture leaving Cooler 2 is
fed to a phase separator (Phase Separator) operating at -50 ºC and 1,5 bar, where a vapor stream
is obtained at the top and a liquid phase is generated at the bottom of this equipment.
The bottom stream of the Phase Separator is sent to a first distillation column (Propylene
Column) operating at 1,5 bar, where almost all the propylene and hydrogen chloride are
obtained at the top stream of this distillation column, while the bottom stream contains almost
all the allyl chloride and both chloropropenes. The top stream of this first distillation column is
mixed with the top stream generated in the phases separator, and the resulting two phase
mixture rich in propylene and hydrogen chloride with traces of allyl chloride (temperature of -
56 ºC) is heated to 10 ºC in a shell and tube heat exchanger (Heater 1) using low pressure
saturated steam (162 ºC, 6,5 bar). The resultant heated gaseous mixture is sent to a gas-liquid
absorber (Absorber) where almost all the hydrogen chloride contained on it is absorbed by
1,480 kg/h of deionized water, thus obtaining at the bottom of this absorber a stream of aqueous
hydrogen chloride (32,4 wt.%), with traces of propylene. This bottom stream is at a temperature
of 120-123 ºC, thus a shell and tube heat exchanger (Cooler 3) is employed to cool it to 35 ºC
using cooling water at 30 ºC as coolant.
The bottom stream of the first distillation column is pumped to a second distillation column
(Concentration Column) to remove almost all the propylene that remains in the feed stream,
which is obtained at the top stream, while the bottom stream of this distillation column contains
the concentrated allyl chloride and both chloropenes. The top stream of the Concentration
Column is mixed with the top stream of the gas-liquid absorber, to obtain a stream rich in
propylene, which is sent to a granular filter (Adsorption Filter) which contains activated carbon
and where all the components, except propylene, are removed by absorption, thus obtaining a
gaseous stream of pure propylene at the top exit of this filter. This gaseous top stream of pure
propylene obtained in the filter is first compressed to 10 bar in a adiabatic reciprocating
compressor (Compressor 1), then it is cooled to 40 ºC in a shell and tube heat exchanger (Cooler
4) against cooling water at 30 ºC.
Next, this cooled stream is compressed again to 20 bar in a adiabatic centrifugal compressor
(Compressor 2), and the resulting compressed gaseous stream is condensed by means of a shell
and tube heat exchanger (Condenser) using cooling water at 2 ºC, thus obtaining a liquid stream
of pure propylene at 45 ºC and 20 bar, which could be recycled back to the allyl chloride
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| 5
production process. The bottom stream of the second distillation column is pumped to a third
distillation column (2-Chloropropene Column), in order to remove the 2-chloropene at the top
stream, while the bottom stream of this third distillation column is pumped to a fourth
distillation column (Allyl Chloride Column) to remove the 2,3-chloropene at the bottom of this
column, thus obtaining 1.337,3 kg/h of a concentrated stream of allyl chloride at the top with a
purity of 99,92 %, being 2-chloropene the main impurity found on it.
Figure 1 presents the process flow diagram of the allyl chloride production process
previously described.
Figure 1. Process flow diagram of the allyl chloride production process.
2.3. Reactions and stoichiometry
The following table shows the main reactions that occur in the fluidized bed reactor, along
with their stoichiometry, percentage conversion and standard heat of reactions [9].
Table 2. Stoichiometry, percentage conversion and standard heat of reaction of the main
reactions involved in the fluidized bed reactor.
No. Stoichiometry Conversion Heat of reaction
1
Allyl chloride formation
C
3
H
6
+ Cl
2
→ C
3
H
5
Cl + HCl
80%
∆H
298
= −112 kJ/mol
2
2-chloropropene formation
C
3
H
6
+ Cl
2
→ C
3
H
5
Cl + HCl
16%
∆H
298
= −121 kJ/mol
3
Dichloropropene formation
C
3
H
6
+ 2Cl
2
→ C
3
H
4
Cl
2
+ 2HCl
3%
∆H
298
= −222 kJ/mol
4
Carbon formation
C
3
H
6
+ 3Cl
2
→ 3C + 6HCl
1%
∆H
298
= −306 kJ/mol
2.4. Selection of the thermodynamic model
The selected thermodynamic model of this study was Soave-Redlich-Kwong (SRK) with no
vapor phase association; immiscible water/hydrocarbon solubility; a global enthalpy model of
SRK; an ideal gas heat capacity of Design Institute for Physical Properties (DIPPR) and steam
table of International Association for the Properties of Water and Steam (IAPWS-IF97).
2.5. Design parameters of the main equipment
The design parameters of the main equipment involved in the allyl chloride production
process simulated in ChemCAD
are shown in Table 3. Those design parameters were selected
following rules of thumbs and suggestions reported in [10], [11], [12], [13] and [14], as well as
taking into account some suggestions of the simulator itself.
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| 6
Table 3. Design parameters of the main equipment involved in the allyl chloride production
process simulated in ChemCAD
.
Equipment Design parameters
Fired heater
Type: Cylindrical type.
Design type: Process heater.
Tube material: Carbon steel.
Efficiency: 0,75
Reactor
Type: Plug Flow.
Length of tubes: 2,5 m.
Diameter of tubes: 0,060 m.
Number of tubes: 150.
Number of steps: 1.
Material: Stainless steel 304
Waste heat boiler
Area: 57,0 m
2
.
Type: Shell and tube/Fixed head.
Material: Stainless steel 304.
Cooler 1
Area: 52,0 m
2
.
Type: Shell and tube/U tube.
Material: Stainless steel 304.
Cooler 2
Area: 50,0 m
2
.
Type: Shell and tube/Fixed head.
Material: Stainless steel 304.
Phase Separator
Type: Cylindrical tank.
Material: Stainless steel 316.
Diameter: 1,8 m.
Height: 3,5 m.
Propylene Column
Type: Cylindrical.
Material: Carbon steel.
Diameter: 2,5 m.
Tray type: Sieve.
Heater 1
Area: 85,0 m
2
.
Type: Shell and tube/Fixed head.
Material: Stainless steel 347.
Absorber
Type: Cylindrical.
Number of stages: 18.
Material: Carbon steel.
Diameter: 2,0 m.
Height: 3,0 m.
Cooler 3
Area: 70,0 m
2
.
Type: Shell and tube/U tube.
Material: Stainless steel 304.
Concentration Column
Type: Cylindrical.
Material: Carbon steel.
Diameter: 1,8 m.
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| 7
Tray type: Sieve.
Adsorption Filter
Material: Carbon steel.
Diameter: 1,5 m.
Height: 2,2 m.
Compressor 1
Type: Reciprocating/Adiabatic.
Driver type: Belt drive coupling.
Motor RPM: 3.600.
Motor type: Explosion proof.
Cooler 4
Area: 50,0 m
2
.
Type: Shell and tube/Fixed head.
Material: Carbon steel.
Compressor 2
Type: Centrifugal/Adiabatic.
Driver type: Belt drive coupling.
Motor RPM: 3.600.
Motor type: Explosion proof.
Condenser
Area: 50,0 m
2
.
Type: Shell and tube/U tube.
Material: Stainless steel 316.
2-Chloropropene Column
Type: Cylindrical.
Material: Carbon steel.
Diameter: 1,6 m.
Tray type: Sieve.
Allyl Chloride Column
Type: Cylindrical.
Material: Carbon steel.
Diameter: 1,6 m.
Tray type: Sieve.
2.6. Mass flowrate of utilities and heat curves of the heat exchangers
In this work, the mass flowrate of the utilities selected to cool/heat process streams in the
shell and tube heat exchangers, as well as the heat curves of those shell and tube heat
exchangers, were obtained. The selected utilities were cooling water at 30 ºC and 3,0 bar,
propylene at -62 ºC and 0,5 bar, saturated steam at 162 ºC and 6,5 bar, and chilled water at 2 ºC
and 3,0 bar. The mass flowrate of the utilities were calculated by employing the “Utility option”
on the “Specifications” tab for each shell and tube heat exchanger, while the heat curves were
obtained selecting the “Heat Curves” option.
3. RESULTS AND DISCUSSION
The following figures display the flowsheet of the allyl chloride production process
simulated in ChemCAD
simulator, corresponding to the reaction (Figure 2a) and the
separation/purification (Figure 2b) sections.
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| 8
a)
b)
Figure 2. Flowsheet of the allyl chloride production process simulated in ChemCAD
,
corresponding to the sections of a: Reaction, b: Separation/purification.
3.1. Mass and energy balances of selected intermediate and final streams
Table 4 shows the mass and energy balances of selected intermediate and final streams,
which were obtained through the simulation of the allyl chloride production process in
ChemCAD
simulator. The results involve the temperature, pressure, flowrate, enthalpy and
vapor mole fraction of those selected streams. Refer to Figure 2 to know to which stream
number the mass and energy balances are referred to.
Table 4. Temperature, pressure, flowrate, enthalpy and vapor mole fraction of selected
intermediate and final streams.
Parameter
Stream number (refer to Figure 2)
5
6
15
16
17
Temperature (ºC)
511,72
511
-50
-50
-50
Pressure (bar)
3,04
2,73
1,68
1,5
1,5
Vapor fraction
1
1
0
0,99
0
Enthalpy (MJ/h)
5.470,2
3.270,97
-3.105,02
-352,51
-2.640,88
Mass flowrate (kg/h)
Allyl chloride
0
1.392,014
1.392,014
0,891
1.391,123
2-Chloropropene
0
117,836
117,836
0
117,836
2,3-Dichloropropene
0
0,789
0,789
0
0,789
Propylene
3.190
2.359,438
2.359,438
110,894
2.248,544
Chlorine
1.400
0,005
0,005
0
0,005
Hydrogen chloride
0
719,901
719,901
151,179
568,721
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| 9
Carbon
0
5,32x10
-5
5,32x10
-5
0
5,32x10
-5
Water
0
0
0
0
0
TOTAL
4.590
4.589,983
4.589,983
262,964
4.327,018
Table 4. Continued…
Parameter
Stream number (refer to Figure 2)
24
29
26
19
31
Temperature (ºC)
10
35
42,52
45,87
-20,94
Pressure (bar)
1,5
1,5
1,4
1,6
2
Vapor fraction
1
0
0
0
0
Enthalpy (MJ/h)
-802,25
-24.489
-357,651
-521,061
-13,182
Mass flowrate (kg/h)
Allyl chloride
14,802
0,198
14,604
1.377,212
13,772
2-Chloropropene
10,042
0,415
9,627
107,795
9,328
2,3-Dichloropropene
3,562x10
-5
7,322x10
-7
3,489x10
-5
0,789
4,412x10
-5
Propylene
2.336,952
63,062
2.273,891
22,485
22,261
Chlorine
0,005
0,005
9,528x10
-6
0,0001
0,0001
Hydrogen chloride
719,731
718,368
1,363
0,169
0,169
Carbon
7,389x10
-16
0
0
5,321x10
-5
7,389x10
-16
Water
0
1.436,153
43,847
0
0
TOTAL
3.081,532
2.218,201
2.343,332
1.508,450
45,530
Table 4. Continued…
Parameter
Stream number (refer to Figure 2)
44
33
34
35
39
Temperature (ºC)
68,41
-31,01
10
10
40
Pressure (bar)
3
2
1,5
1,5
10
Vapor fraction
0
0,45
1
0,18
1
Enthalpy (MJ/h)
-462,04
-370,83
1.004,49
-712,05
1.064,12
Mass flowrate (kg/h)
Allyl chloride
1.363,44
28,376
0
28,375
0
2-Chloropropene
98,467
18,955
0
18,955
0
2,3-Dichloropropene
0,789
7,901x10
-5
0
7,901x10
-5
0
Propylene
0,225
2.296,151
2.273,19
22,961
2.273,19
Chlorine
5,587x10
-6
0,0001
0
0,0001
0
Hydrogen chloride
6,489x10
-5
1,532
0
1,532
0
Carbon
5,321x10
-5
7,39x10
-16
0
7,39x10
-16
0
Water
0
48,847
0
43,847
0
TOTAL
1.462,921
2.388,861
2.273,19
115,670
2.273,19
Table 4. Final…
Parameter
Stream number (refer to Figure 2)
46
47
48
49
43
Temperature (ºC)
59,10
83,65
94,04
96,39
45
Pressure (bar)
3
3,5
4
4.1
20
Vapor fraction
0
0
0
0
0
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| 10
Enthalpy (MJ/h)
-57,36
-372,82
-345,29
-3,94
355,820
Mass flowrate (kg/h)
Allyl chloride
13,634
1.349,805
1.336,307
13,498
0
2-Chloropropene
97,482
0,984
0,984
0,0001
0
2,3-Dichloropropene
1,096x10
-11
0,789
0,0079
0,781
0
Propylene
0,225
0
0
0
2.273,19
Chlorine
5,587x10
-6
0
0
0
0
Hydrogen chloride
6,489x10
-5
0
0
0
0
Carbon
7,389x10
-16
5,321x10
-5
7,39x10
-16
5,32x10
-5
0
Water
0
0
0
0
0
TOTAL
111,341
1.351,578
1.337,298
14,279
2.273,19
The outlet stream of the fluidized bed reactor (stream 6 in Figure 2a) contains allyl chloride
in 30,32 %, unreacted propylene in 51,40 % and 15,68 % of hydrogen chloride. About 830,562
kg/h of propylene reacts with almost all the 1,400 kg/h of chlorine, in order to produce
1.392,014 kg/h of allyl chloride. It’s worth noting that an insignificant amount of carbon is
produced in the reactor (5,32x10
-5
kg/h) which agrees with the values suggested by [9].
In the phase separator, a vapor stream is obtained at the top of this equipment (stream 16)
with a total mass flowrate of 262,964 kg/h and with the following composition: 42,17 % of
propylene and 57,49 % of hydrogen chloride with traces amounts of allyl chloride, while at the
bottom a liquid stream (stream 17) is obtained with a total mass flowrate of 4.327,018 kg/h,
where the main chemicals found on it are propylene (51,96 %), allyl chloride (32,15 %) and
hydrogen chloride (13,14 %).
In the propylene column, about 99,00 % of the allyl chloride fed to this distillation column
is obtained at the bottom (stream 18, 1.377,212 kg/h), while 91,48 % of the 2-chloropropene fed
to this column is also obtained at the bottom (107,795 kg/h). Concerning the propylene
component, about 99,00 % of this chemical is recovered at the distillate stream (stream 18) in
this distillation column (data not shown), with a mass flowrate of 2.226,059 kg/h, while 568,552
kg/h of hydrogen chloride are also obtained in this distillate stream. The composition of the
distillate stream in the propylene column is 78,97 % propylene and 20,17 % hydrogen chloride,
with minor traces of allyl chloride and 2-chloropropene (data not shown).
In the absorber, a liquid stream having a total mass flowrate of 2.218,201 kg/h is obtained at
the bottom (stream 25) with the following mass concentration: hydrogen chloride (32,4 %),
water (64,74 %) and propylene (0,028 %), that is, an aqueous solution of hydrochloric acid is
obtained at the bottom stream of this equipment, which could be commercialized as a
byproduct. The top stream of the absorber (stream 26) contains propylene with a mass
concentration of 97,04 % and a mass flowrate of 2.273,891 kg/h, with traces of allyl chloride, 2-
chloropropene and hydrogen chloride.
In the concentration column, around 99 % of the propylene fed to this distillation column is
obtained at the distillate (stream 31), with a mass flowrate of 22,261 kg/h. The percentage mass
composition of this distillate stream is the following: allyl chloride (30,25 %), 2-chloropropene
(20,49 %) and propylene (48,89 %). The bottom stream of the concentration column (streams 30
and 44) has a total mass flowrate of 1.462,920 kg/h and contains the following chemicals: allyl
chloride (93,19 %) and 2-chloropropene (6,73 %).
The adsorption filter separates propylene from the rest of the chemicals at a rate of 99,00 %,
which is obtained at the top stream of this equipment (stream 34) in gaseous state with a mass
flowrate of 2.273,19 kg/h. The bottom liquid stream of this filter (stream 35), which has a total
mas flowrate of 115,670 kg/h, contains allyl chloride (24,53 %), 2-chloropropene (16,38 %),
InGenio Journal, 8(1), 156–173 166
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| 11
propylene (19,85 %) and water (37,91 %). It’s recommended to send this bottom liquid stream
to a wastewater treatment system before dispose it in the environment.
Regarding the 2-chloropropene column, about 98,99 % of the 2-chloropropene fed to this
distillation column is separated and obtained in the top stream (stream 46), with a mass flowrate
of 97,482 kg/h. The top stream of the 2-chloropropene column is composed by 2-chloropropene
(87,55 %) and allyl chloride (12,24 %), with traces of the rest of the chemicals, except water.
This stream of chloroprene could be further purified to commercialize it as a byproduct with a
higher purity. The bottom stream of the 2-chloropropene column (streams 45 and 47) contains
allyl chloride with a purity of 99,86 % and a mass flowrate of 1.349,805 kg/h, with minor traces
of 2-chloropropene and 2,3-dichloropropene.
Finally, in the allyl chloride column, about 1.336,307 kg/h of allyl chloride are obtained at
the top stream (stream 48) with a purity of 99,92%, while the bottom stream of this column
(stream 49, 14,279 kg/h) contains allyl chloride (94,53 %) and 2,3-dichloropropene (5,46 %) as
the main products. About 99,00% of the allyl chloride fed to this distillation column is separated
and obtained at the top stream.
3.2. Operating parameters of the main equipment
Below are shown various operating and design parameters calculated by ChemCAD
simulator for the main equipment involved in the simulation flowsheet.
Fired heater:
• Heat absorbed: 4.088,08 MJ/h.
• Reactor:
• Heat duty: - 2.199,23 MJ/h.
Waste heat boiler:
• Heat duty: 2.864,24 MJ/h.
• Log Mean Temperature Difference (LMTD): 206,97 ºC.
• LMTD Correction factor: 0,898.
• Calculated overall heat transfer coefficient (U): 75,09 W/m
2
.K.
Cooler 1:
• Heat duty: 1.040,36 MJ/h.
• LMTD: 67,32 ºC.
• LMTD Correction factor: 0,926.
• Calculated U: 89,09 W/m
2
.K.
Cooler 2:
• Heat duty: 2.471,39 MJ/h.
• LMTD: 35,84 ºC.
• LMTD Correction factor: 0,50.
• Calculated U: 766,09 W/m
2
.K.
Propylene Column
• Condenser duty: - 2.928,26 MJ/h.
• Reboiler duty: 3.103,19 MJ/h.
• Minimum stages: 4.
• Reflux ratio, minimum: 0,024.
Heater 1:
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| 12
• Heat duty: 1.495,14 MJ/h.
• LMTD: 182,99 ºC.
• LMTD Correction factor: 1,0.
• Calculated U: 26,70 W/m
2
.K.
Cooler 3:
• Heat duty: 547,24 MJ/h.
• LMTD: 17,31 ºC.
• LMTD Correction factor: 0,5.
• Calculated U: 250,88 W/m
2
.K.
Concentration Column:
• Condenser duty: - 45,23 MJ/h.
• Reboiler duty: 90,79 MJ/h.
• Minimum stages: 5.
• Reflux ratio, minimum: 0,694.
Compressor 1 (Reciprocating):
• Theoretical power: 261,054 MJ/h.
• Calculated head: 12.163,5 m.
• Cp/Cv: 1,170.
Cooler 4:
• Heat duty: 247,496 MJ/h.
• LMTD: 14,29 ºC.
• LMTD Correction factor: 0,5.
• Calculated U: 192,33 W/m
2
.K.
Compressor 1 (Centrifugal):
• Theoretical power: 85,95 MJ/h.
• Calculated head: 4.081,07 m.
• Cp/Cv: 1,251.
Condenser:
• Heat duty: 809,42 MJ/h.
• LMTD: 34,76 ºC.
• LMTD Correction factor: 0,718.
• Calculated U: 180,01 W/m
2
.K.
2-Chloropropene Column:
• Condenser duty: - 76,92 MJ/h.
• Reboiler duty: 108,71 MJ/h.
• Minimum stages: 17.
• Reflux ratio, minimum: 14,888.
Allyl Chloride Column:
• Condenser duty: - 944,20 MJ/h.
• Reboiler duty: 967,78 MJ/h.
• Minimum stages: 9
• Reflux ratio, minimum: 0,408.
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| 13
According to the results shown above, the calculated value of the heat absorbed for the fired
heater (∼ 4,1 GJ/h) is within the range reported by [13] of 0,5 to 21 GJ/h and the range reported
by [9] of 4,0 – 5,4 GJ/h for this type of fired heater. Likewise, the calculated value of the heat
duty for the fluidized bed reactor (- 2.199,23 MJ/h) is close to the value reported by [9] of -
2.188 MJ/h.
In this study, we selected a shell and tube heat exchanger to simulate the waste heat boiler,
thus the results of the operating parameters obtained for this type of equipment are similar to
those described for typical heat exchangers, not specifically boilers. The value of the calculated
heat duty for the waste heat boiler (2.864,24 MJ/h) is very similar to that reported by [9] of
2.850 MJ/h, while the calculated value for the overall heat transfer coefficient (75,09 W/m
2
.K)
is within the range reported by [14] of 30-100 W/m
2
.K.
The Cooler 1 had a value for the heat duty of 1.040,36 MJ/h, which is comparable to the
value of the heat duty stated by [9] of 1.025 MJ/h, while the value of the calculated overall heat
transfer coefficient for this heat exchanger (89,09 W/m
2
.K) is within the range reported by [14]
of 20-300 W/m
2
.K.
Regarding the Cooler 2, the value of the heat duty was of 2.471,39 MJ/h (comparable to the
range reported by [9] for the heat duty), while the calculated overall heat transfer coefficient had
a value of 766,09 W/m
2
.K, which is within the range reported by [14] of 700-1,000 W/m
2
.K for
condensers.
The Heater 1 had a heat duty of 1.495,14 MJ/h (analogous to the range reported by [9] for
the heat duty) and a calculated overall heat transfer coefficient of 26,70 W/m
2
.K, which is below
the range reported by [14] of 30-300 W/m
2
.K.
Concerning the Cooler 3, the heat duty was of 547,24 MJ/h, while the calculated overall
heat transfer coefficient was of 250,88 W/m
2
.K, which is within the range of 250-750 W/m
2
.K
reported by [14].
The Cooler 4 had a heat duty of 247,496 MJ/h and a calculated overall heat transfer
coefficient of 192,33 W/m
2
.K, which is between the range reported by [14] of 20-300 W/m
2
.K.
Finally, the Condenser had a heat duty of 809,42 MJ/h (similar to the range stated by [9] for
the heat duty of a condenser) and a calculated value for the overall heat transfer coefficient of
180,01 W/m
2
.K, which is below the range reported by [14] of 700-1.000 W/m
2
.K.
In this case, the waste heat boiler had the highest value of the heat duty, which is due to the
fact that is in this heat exchanger where water is vaporized to produce saturated steam using the
hot gaseous mixture exiting the reactor as the heating agent, while the Cooler 4 had the lowest
value of the heat duty because this heat exchanger cools down the gaseous pressurized
propylene stream coming from the reciprocating compressor from 99,7 ºC to 40 ºC using
cooling water at 30 ºC. With respect to the calculated value of the overall heat transfer
coefficient, the Cooler 2 and Heater 1 had the highest and lowest values of this parameter,
respectively.
Regarding to the compressors, the reciprocating compressor had a value of the theoretical
power of 261,054 MJ/h (∼ 72,52 kW), which is between the range reported by [15] of 7,5 kW -
9 MW for reciprocating compressors, while the centrifugal compressor had a value of 85,95
MJ/h (∼ 23,87 kW) for the theoretical power, which is below the range reported by [15] of 75-
97 MW for centrifugal compressors. Lastly, the values of the calculated head were 12.163,5 m
and 4.081,07 m for the reciprocating and centrifugal compressor, respectively.
The Propylene Column had a condenser duty of - 2.928,26 MJ/h, a reboiler duty of 3.103,19
MJ/h and will require 4 stages minimum with a minimum reflux ratio of 0,024. The condenser
duty and the reboiler duty for the Concentration Column were - 45,23 MJ/h and 90,79 MJ/h,
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| 14
respectively, while it will require 5 stages minimum and a minimum reflux ratio of 0,694. In
case of the 2-Chloropropene Column, the condenser duty and the reboiler duty were - 76,92
MJ/h and 108,71 MJ/h respectively, while the value for the minimum stages was 17 with a
minimum reflux ratio of 14,888. Finally, the Allyl Chloride Column had a condenser duty of -
944,20 MJ/h, a reboiler duty of 967,78 MJ/h, 9 minimum stages and a minimum reflux ratio of
0,408.
3.3. Required flowrate of utilities
ChemCAD
simulator presents an option to calculate the flowrate of utilities (i.e. cooling
water, steam, etc.) to achieve a predetermined heat exchange duty in heat exchangers. In this study
we utilized this option to know the mass flowrate of the utilities selected, which were cooling
water (30 ºC, 3 bar), steam (162 ºC, 6,5 bar), chilled water (2 ºC, 3 bar) and propylene (- 62 ºC,
0,5 bar), in order to heat/cool a particular process stream. Figure 3 shows the calculated flowrate
of each utility selected in this study.
Figure 3. Calculated flowrate of each utility selected in this study.
As described in Figure 3, Cooler 1 needs the highest mass flowrate of cooling water with
24.905,37 kg/h, which is due to the fact that in this exchanger the hot gaseous mixture stream
coming from the waste heat boiler is cooled from 200 ºC to 50 ºC (having a temperature
difference of 150 ºC), thus requiring a high amount of cooling water to carry out this cooling
service. On the other hand, Cooler 4 requires the lowest mass flowrate of cooling water
(1.183,43 kg/h) since this heat exchanger cools the propylene gaseous stream coming from the
reciprocating compressor from 100 ºC to 40 ºC, with a temperature difference of only 60 ºC.
Heater 1 requires a steam mass flowrate of 2.540 kg/h, which could be classified as adequate
[9], Cooler 2 requires a propylene mass flowrate of 4.954,69 kg/h, which can be classified as
relatively high because this exchanger condenses the gaseous stream exiting the Cooler 1 from
50 ºC to -50 ºC (temperature difference of 100 ºC), thus requiring this high mass flowrate of
propylene to obtain a condensed liquid stream containing the allyl chloride, the chlorinated
hydrocarbon derivatives as well as the unreacted propylene. Finally, the Condenser requires a
chilled water mass flowrate of 4.029,15 kg/h, which can be classified as acceptable because this
heat exchanger carries out the condensation of the gaseous pressurized propylene stream from
78 ºC to 45 ºC, thus obtaining liquid propylene at the heat exchanger outlet.
3.4. Heat curves
Figure 4 presents the heat curves of each shell and tube heat exchanger employed in the
simulation study.
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| 15
a)
b)
c)
d)
e)
f)
g)
Figure 4. Heat curves of each shell and tube heat exchanger employed in the simulation study,
corresponding specifically to a: Waste heat boiler, b: Cooler 1, c: Cooler 2, d: Heater 1, e:
Cooler 3, f: Cooler 4, g: Condenser.
Figure 4a) shows that a change of pattern occurs for the cooling water at the 12 % length
and 162 ºC, thus indicating that a phase change takes place from liquid to vapor, thus obtaining
saturated steam, while the heat curve of Stream 6 (hot gaseous mixture exiting the reactor) has a
linear trend, indicating that this stream cools down from 511 °C to 200 °C without phase
change.
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| 16
Regarding the heat curve obtained for the Cooler 1 (Figure 4b) both the Cooling water
stream and Stream 8 (cooled gaseous stream coming from the waste heat boiler) don’t undergo
phase change, which is indicated by the linear tendency of the two heat curves.
Concerning the heat curve of Cooler 2 (Figure 4c), both the Propylene stream and Stream 11
(cooled gaseous stream coming from the Cooler 1) experience phase change. In the case of the
Propylene stream, it shows a linear trend from -62 °C to -58 °C of temperature and from 0 % to
93 % length, to then be subjected to a phase change verified by the pattern change of its heat
curve (an increasing linear trend) until reaching -30 °C (the outlet temperature). This phase
change is confirmed by checking the vapor mole fraction of both the inlet and outlet streams for
Propylene stream in the simulation flowsheet, where the inlet stream has a vapor fraction of
0,00 (liquid) while the vapor fraction of the outlet stream is 1,00 (vapor). That is, the Propylene
stream is vaporized. For the heat curve of Stream 11, it undergoes sensible heat until reaching
20 °C and 92% length of the heat exchanger, to then experience phase change from this point to
the outlet temperature of this stream (-30 °C), which is corroborated by the change of pattern of
the heat curve, thus obtaining a liquid stream at the outlet. This phase change is proved by
checking the vapor mole fraction of both the inlet and outlet streams of Stream 11 in the
simulation flowsheet, where the inlet stream presents a vapor mole fraction of 1,00 (vapor) and
the outlet stream has a vapor mole fraction of 0,00 (liquid), i.e., Stream 11 undergoes
condensation.
In the case of the heat curve of Heater 1 (Figure 4d), the Stream 20 suffers phase change
taking into account the pattern of its heat curve. Specifically, this stream is heated without phase
change (sensible heat) from -56 °C to -43 °C and 83 % length, to then undergo a phase change,
which is demonstrated by the increasing linear trend occurring from 88 % length and -36 °C
approximately, to the final length of the heat exchanger and the outlet temperature (10 °C). This
is corroborated by checking the vapor mole fraction of this stream in the simulation flowsheet,
where it is 0,09 at the inlet (two phase vapor-liquid flow) and 1,00 (vapor) at the outlet of this
heat exchanger, i.e., Stream 20 vaporizes. On the other hand, the Steam stream doesn’t
experience phase change (i.e. condensation), which is verified by the constant linear trend of its
heat curve at the temperature of 162 °C.
The heat curve of Cooler 3 (Figure 4e) displays two phase changes for both the Cooling
water stream and Stream 25. The Cooling water stream is heated under sensible heat from 30 °C
to 80 °C and 15% length approximately, to then undergo phase change (condensation) at this
point, showed by the change of pattern of its heat curve, thus obtaining a vapor stream at the
outlet. The Stream 25 is cooled under sensible heat from 122 °C until reaching a point of 104 °C
and 98 % length, and then suffers phase change (condensation) demonstrated by the decreasing
curved trend of its heat curve. This is verified by checking the vapor mole fraction of both the
inlet and outlet streams of this stream in the simulation flowsheet, where the vapor mole
fraction has value of 1,00 (vapor) at the inlet and a value of 0,00 (liquid) at the outlet, i.e.
condensation occurs.
In relation to the heat curve for Cooler 4 (Figure 4f), both the Stream 36 and the Cooling
water streams don’t experience phase change, which is certified by the linear trend of both heat
curves. That is, the Cooling water stream is heated from 30 °C to 80 °C without evaporation,
while the Stream 36 is cooled from 100 to 40 °C without condensation.
Finally, the heat curve obtained for the Condenser (Figure 4g) shows that the Stream 40
goes through cooling without phase change from 78 °C to 48 °C and 83 % length
approximately; to then go through phase change from this point until reaching the outlet
temperature (45 °C). This is validated by checking the vapor mole fraction of both the inlet and
outlet streams of this stream in the simulation flowsheet, where the inlet stream has a vapor
InGenio Journal, 8(1), 156–173 172
InGenio Journal, 8(1), 1–4
| 17
mole fraction of 1,00 (vapor) while the vapor mole fraction of the outlet stream is 0,00 (liquid),
thus occurring condensation. In case of the heat curve obtained for the Chilled water, its linear
trend indicates that this stream doesn’t undergo phase change, i.e. it’s heated from 2 °C to 50 °C
without vaporization.
4. CONCLUSIONS
An innovative ChemCAD
simulation model was obtained in this study in order to
conceptually design an allyl chloride production process by the propylene chlorination route. By
means of the simulation results, the temperature, pressure, vapor mole fraction, enthalpy and
mass flowrate of the intermediate and final streams were known, as well as various important
operating and design parameters of the main equipment included in the simulation flowsheet.
Likewise, the required flowrate of utilities and the heat curves of all the shell and tube heat
exchangers employed in the production process were also determined. Allyl chloride is obtained
at the distillate of the last distillation column with a flowrate and purity of 1.336,307 kg/h and
99,92 %, respectively, while 2.273,189 kg/h of pure liquid propylene, 2.218,202 kg/h of an
aqueous solution of HCl 32,4 % wt. %, and 97,482 kg/h of 2-Chloropropene with a purity of
87,55 % are also generated as byproduct in the simulated process. The ChemCAD
simulation
model obtained in this work could be used for future optimization studies, throughput increment
assessments, and sensitivity analysis. The results of this simulation study, mostly the mass and
energy balances and the equipment design and operating parameters, can be successfully
applied and implemented at industrial scale due to the its reliability, scalability, operability and
consistency, in order to erect the proposed commercial-scale allyl chloride production plant. It’s
recommended carrying out further calculation and simulation analyses to determine several
important financial indicators such as net present value, internal rate of return, payback time,
return of investment, unit production cost, annual operating costs and others, to verify the
economic feasibility and viability of this chemical engineering design project.
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