I Advancement II Project

PROCESS isopropylbenzene
"CUMENE"
Julian Mauricio Rojas 1 Labrador
jmlabradorr@unal.edu.co1
Process engineering

Department of Chemical Engineering, Faculty of Engineering and Architecture

Summary
In the petrochemical production development isopropylbenzene (cumene) has been investigated so has been
obtained cleaner and more efficient processes. The cumene production process becomes most important when
the intermediate mechanism for the production of phenol and acetone. Herein the cumene process, which
addresses a study on the transformation path, raw material used in the process, and a technical and economical
analysis of the process, by addressing its operating conditions, characterizing the present equipment is presented
and studying the relevant balances simulándonos and proposing a process in Aspen Plus 9.
Keywords:Cumene, Kinetics, Production, Oil

Introduction

The production process of isopropylbenzene (cumene), used as raw materials benzene and propylene, by the
alkylation, in this process a compound is given unwanted, diisopropylbenzene (DIPB) as the main product. In
the transalkylation step the DIPB is reacted with benzene to form more IPB. This process can be carried out in
liquid or gas phase, which determine the type of alkylation reactor used. Within the process is considered a
power in excess of benzene to minimize alkylation products poly [1].

The process allows for Cumene with 99.5% purity and has a selectivity of 97% based on benzene; Cumene is
used mostly for the production of acetone and phenol, however, the production of phenol and acetone produced
does not match the Phenol relationship and Acetone consumed, therefore, as demand Phenol (Bisphenol A) is
greater, this is the limiting compound and determines the capacity utilization and production of cumene as a
raw material [1].

The alkylation of benzene with ethylene is carried out, currently, according to two manufacturing processes
(.DELTA.H = - 113 kJ / mol):

Image 1. Cumene reaction [two]

BACKGROUND

Aromatic hydrocarbons, mainly benzene, toluene, xylenes and ethylbenzene, are basic compounds for synthesis
of plastic raw materials, synthetic rubbers and other organic products of industrial interest [2]. Most oil is
obtained, and only a small proportion of coal. Although the content of aromatics originally present in both
petroleum and coal is low in certain heat treatment processes or catalytic coking and refinery produced in
significant proportions that make economic separation [3].
1. Transformation path

1.1. Processes and types of catalysts used in the production of Cumene

the alkylation and transalkylation occur in the production of Cumene which are not desired in the
production process of Cumene and not taken into account in the kinetics because they occur very
quickly putting excess benzene shown:

Image 2. Reactions alkylation and transalkylation [4]

In 1992 the production of Cumene produced by the alkylation of benzene with propylene, using as
catalysts phosphoric acid "solid" and aluminum chloride, the process conditions were, pressure (3 to
4.1 MPa), temperature ( 180-230 ° C) and a ratio of benzene to propylene of 5 to 7 [5].

In recent years; the tendency is to look for catalysts that make the process friendlier to the environment
and for this reason have developed new catalysts as those based on zeolites of a picture of these
processes generated occurs during recent years

Table 1. zeolite types [4]

First year No. of commercial authorized capacity (million

Process
announced units. metric tons per year)
Mobil - Badger 1993 7 3125
UOP Q-Max nineteen 4 625
ninety five
CDTech nineteen two 440
CDCumene ninety five
Enichem nineteen one 265
ninety five
Dow Chemical 3- 1992 one 410
DDM

These new processes have practically replaced today Monsanto process, the advantages in the
operation and performance in the production of cumene; one process that is widely used is the Mobil
- Badger which uses a catalyst called MCM-22, which has a high selectivity for monoalkylation; also
it generates very few products which results Cumene high purity around 99.7 to 99.97% w / w. [5] The
catalyst has a shelf life of 5 years, which gives a great advantage over the old processes and others that
exist today. Then a diagram where the process described is diagrammed shown:
 diagram 1 Badger process [5]

tables where one can see the advantages of this in relation to other types of zeolite used in the market
today is also presented.

table 2. AdvantageMCM-22 zeolite other [6]

OTHER ZEOLITES MCM-22

CUMENE (WT%) 99.90 99.95-99.97
ETHYLBENZENE (PPM) 200 25
N-PROPYLBENZENE (PPM) 300 200

In general the processes presented in the table are based on zeolite catalysts which generate less costs
due to corrosion problems and reduced power consumption in the separation process or purification
mainly because fewer byproducts are generated [5].

1.2. Obtaining isopropylbenzene (cumene) by alkylation of benzene with ethylene

The cumene is obtained by alkylation of benzene with propylene instead of ethylene using the same
catalyst (Al2O3, phosphoric acid, etc.) although alkylation with propylene easier and faster than with
ethylene due to the formation of a secondary carbocation . Again polyalkyl (di-, tri- and
tetraisopropilbencenos) they occur with a configuration that depends on the type of catalyst employed.
These polyalkylbenzenes can be converted into cumene in the presence of benzene and catalysts which
are active for transalkylation. [7]

Among the numerous processes developed on an industrial scale, most supported phosphoric acid used
and performs the liquid phase alkylation without recycle of polyalkylbenzenes as phosphoric acid is
not active for transalkylation. Although this process is the most commonly used it is the least efficient
for my project, therefore, the best process is to mobil-Badger with the catalystMCM-22. [5]

1.3. Process description

 In the process a mixture of excess benzene, propylene and propane (as a diluent) pumped through
several reactors in parallel is used. The heat generated in the reaction vaporizes propane and propylene,
bubbling in the liquid. The stream exiting the reactor enters a RECT column in which a flash
vaporization occurs. Rising vapors of benzene and cumene is recovered by cooling and depressurizing
the DP column, wherein the feed benzene is also introduced, for predrying. On top of this column goes
a mixture of propane and water. [5]

Water is purged of the propane is returned to the column as reflux and the remainder also purged.
RECT tails column are distilled to separate cumene from benzene and excess of heavy products, which
are burned.
In the reactor a small amount of water is also introduced, to maintain catalyst activity, which
accumulates in the bottom of the column and must be purged RECT.
The propylene used as raw material may be even a fraction C3 without prior separation of propane (40
- 60% propylene). The propylene conversion is 99.35%,
with a selectivity higher than 92% Cumene. [5]

1.3.1. Equipment used

 an adiabatic reactor CSTR, which will have two streams of liquid and a steam turbine is
used

 mixer at the reactor inlet which combine propylene with benzene

 two heat exchangers (coolers) is used to the reactor outlet for cooling and another output
Distiller 1

 Distillation Column RADFRAC 1 at this point propane, excess benzene, cumene is

separated. To look at the number of dishes have to do a sensitivity analysis and
optimization.

 Distillation Column RADFRAC 2 at this point, benzene, cumene is separated. To look

at the number of dishes have to do a sensitivity analysis and optimization

 Distillation Column 3 RADFRAC at this point separates the cumene, the

polypropylbenzene. To look at the number of dishes have to do a sensitivity analysis and
optimization.

2. Raw materials used

2.1. Benzene

Benzene is a poly-unsaturated aromatic type, hydrocarbon listed among the 20 chemicals higher
production volume. Benzene usually is used as raw material for the production of other products
such as plastics, resins, nylon and Plus rubbers, lubricants, dyes, detergents, drugs, other polymers
between others. From the physico-chemically, Benzene (C₆H₆) Has a molecular structure
hexagonal (6 carbons, 3 double bonds), with resonance characteristics which achieve inherent
 stability of the aromatic molecules. Benzene is a colorless liquid with a sweet and slightly bitter
flavor, is poorly soluble in water, highly flammable and volatile. [9]

image 3. Benzene molecular structure

2.1.1 Toxicity

Breathing, inhale, inhale, inspire or ingesting benzene levels too high can cause death, while low
levels can cause drowsiness, dizziness, hallucinations, rapid heartbeat or tachycardia, headaches,
migraines, tremors, shivering, confusion and unconsciousness. Eating or drinking high levels of
benzene can cause vomiting or heartburn, stomach irritation, stomach ulcers, dizziness, drowsiness
or seizures; and ultimately death. Long-term exposure to benzene occurs in the blood. Benzene
causes harmful effects on the bone marrow and can cause a decrease in the number of red blood
cells, leading to anemia suffer. Benzene can also cause bleeding and damage to the immune system,
thus increasing the chances of infection by immunosuppression. The harmful effects of benzene
increases with alcohol consumption. Some studies on a sample of women who breathed high levels
of benzene for many months had revealed that irregular menses, with uncontrollable bleeding from
the vagina, as well as decrease in the size of their ovaries. [8]

2.2. propylene

Propylene (also called propene) is an alkene comprises 3 to 6 carbon atoms Hydrogen addition one
double bond. It is an odorless, colorless hydrocarbon, and the second compound most widely used in
the chemical industry worldwide. It is obtained as a product of petroleum distillation treatment. Its
main use is for the synthesis of polypropylene and acetone production. The number of reactions and
therefore products from propylene as raw material is very large. [9]

picture 4. molecular structure of propylene

2.2.1. Toxicity

Propylene is non-toxic, colorless, odorless and is more heavier than air so that an escape of this
gas is directed to the lower parts. The risk related primary leakage of this gas is combustion or
explosion mixtures with air is a non-toxic and with a slight anesthetic effect and narcotic gas. The
exposure to high concentrations may cause asphyxiation if the oxygen content is reduced 21% to
about 15%. [8]

3. Table of kinetic parameters

 Isopropylbenzene (cumene) is produced by the reaction of propylene and benzene over a catalyst. [9] Where
benzene is placed in excess to avoid creating other undesirable reactions. The affinity of the first reaction
is that in May the second reaction, as it is put in excess benzene, ensures the best performance thus
promoting the first reaction. [10]

Primary reaction

Rate law 𝑟1 = 𝐾1 𝐶𝑝 𝐶𝑏

constant K 3,5 ∗ 104 𝐸𝑥𝑝 (−24,90⁄𝑅𝑇)

Undesired side reaction

Rate law𝑚𝑜𝑙⁄𝑔𝑐𝑎𝑡 𝑆 𝑟2 = 𝐾2 𝐶𝑝 𝐶𝑏

constant K 2,9 ∗ 106 𝐸𝑥𝑝 (−35,08⁄𝑅𝑇)

Where:
 Units activation energy are kcal / mol,
 The concentration units are mol / L temperature is in K
 The units are temperature in Kelvin.

4. Output

The production plant Isopropylbenzene a reaction catalyst in the liquid phase, is estimated to be produced
annually about 91,153.23 tons / year Cumene 99% purity. From 10% of domestic production of benzene
(flows our process do not match 10% but is estimated below this), because at this stage with a zeolite catalyst
having higher performance and economy it is assumed that a year is equal to 8000 hours, with the remaining
time used for general plant maintenance, and that daily work they are distributed in three shifts of 8 hours
each.[12]

5. Location

The location of the plant depends on various factors, they have a weight according to its importance
 5.1. Factors to Consider:
a) Availability.
Availability of raw materials such as propylene, was mainly has in mind because it is currently
promoting the industrialization of natural gas in Colombia, it is considered as the starting point for
the availability of raw materials. Benzene is not taken into account because of their availability
b) markets
This factor will depend on the use of cumene in the Colombian industry, the main applications for
cumene in our country are as diluent for paints, lacquers and enamels, and as a component of some
solvents.
US import large volumes of Cumene from Colombia, for the production of phenol.
c) Power availability
Process cumene production, the principal raw material propylene as the limiting reagent, which is
obtained exotherm, the use of natural gas could be a solution to our process.
d) Weather
Moreover, climatic and environmental factors are to study when deciding the location of an
industrial plant. Industrial processes should be installed as far as possible from inhabited areas due
to noise pollution among other things. Extreme climates are also a limiting factor for the location,
since the machines do not work well, or spoil before, in very cold, very warm, very dry or very
humid climates, but this depends also on the material and maintaining plant.
e) Labor supplies
This is the most important factor when choosing the location of a plant. But it is not only an
important factor in the cost of labor but also the quality of labor and the availability of the same.

I chose an alternative location by the same factors mentioned, which is the city of Barrancabermeja in Santander
department, because it has a good geographic location, have access to Magdalena River and routes 4 generation
in Colombia. [13] Apart from this we Ecopetrol refinery, which could provide us with benzene. Canyon's
population and labor rate is optimal for the location of my Cumene plant. Having an impact on the economy of
the municipality, also unemployment is reduced and improving the quality of life in Barrancabermeja. [11]

6. Methodology

To simulate the manufacturing process Cumene (isopropylbenzene) by the reaction of benzene

with propylene: Benzene + Propylene Cumene →

The reaction is carried out in a reactor of perfect mixing and not take into account the catalyst, the
stream is preheated to 170 ° C 27 conversion being the same, compared to 95% propylene. The
Rplug reactor is adiabatic and the pressure at the outlet thereof, as shown in diagram 2. The reaction
is exothermic so the stream leaving the reactor passes through a heat exchanger where it is cooled
from 199 to 100 ° C.

In the first column propane is distilled, which does not react and funds have cumene, excess
benzene that did not react which can recirculate but we do not because of problems Technical
simulation but in economic analysis taking into account, this bottoms stream enters another column
2, which separates me benzene cumene, benzene exits the dome and cumene following the next
 column 3, cumene is mixed with diisopropylbenzene which is an undesired product and we have
to purify it, the diisopropylbenzene we can use to improve the octane rating of gasoline.

Each column that was used in the system is a RADFRAC which is a model applicable in a wide
range of situations and also provides sufficient complexity and rigor in the calculation, compatible
both with simplicity in model building column ASPEN PLUS. It is a distillation column model
rather more stringent than the Underwood-Fenske based or similar and simpler than those used for
distillation of crude oil; but has sufficient rigor for conventional distillations. [14]

5. Results and discussion

5.1. Basic modeling (Matlab)

5.1.1. tube model exchanger tube in Matlab: He was chosen exchanger tube in tube, with
a service flow steam to heat the mixture of propylene, benzene.

My Mo
Ti 25 ° C To 170 ° C
Mix flow Mix flow

Figure 1. Exchanger tube in tube

respective energy balance is established:

mass vapor clears

a suitable U was selected for this system, as the interchange design was a tube in tube heat
exchanger of carbon steel, the service flow was vapor stream to heat the mixture was benzene,
propylene. Giving as a result the following graphs.
 Grafica A. IC heat exchange tube in tube

For a flow of 70323.32 kg / h is required 1911.947 L / min of steam. This is logical since the flow
of the mixture is very high.

5.1.2. Reactor PFR model in Matlab

the reaction of benzene and propylene was carried out in a PFR reactor which gave a 7
meter which helped us give notion in the reactor volume for programming Aspen plus.

Graphics B and C. PFR reactor length depending on the conversion and flow

5.2. Modeling and simulation (Aspen Plus)

diagram 2. cumene process in Aspen plus
 as shown in the diagram we see the mass flows and production used in end Cumene B14
distillation column, which showed a greater increase us previously budgeted, giving 4
times, representing us greater benefit.

5.3. Pretreatment of benzene and propylene

Pretreatment of our raw materials is heat and pressure increase to 35.5 bar benzene and
cooled to 25 ° C if necessary, for the propylene alone hence heat, as this is liquid at 35.5
bar (liquid) , it needs a compressor or pump that increases the pressure and I a heat
exchanger, this heat may come from other equipment operation as it is not required to carry
high temperatures.

diagram 3. pretreatment

5.4. Reaction zone

The reactor used was a Rplug which worked adiabatically and with a length of 7 meters
and a diameter of 1.7 meters and a conversion of 0.999 because benzene is placed in excess,
by throwing the following results:

CORRI-2 CORRI-3
Benze-01 Kmol / HR 496.90 403.58
ISOPR-01 Kmol / HR 0.0497 86.67
PROPY-01 Kmol / HR 100 0
PROPA-01 Kmol / HR 5 5
P-DII-01 Kmol / HR 0 6,691

5.5. Analysis in each distillation column

To analyze the number of stages encada column was a sensitivity analysis and optimization in
the case of the COLUMN-1 COLUMN 2 COLUMN--3 columns. A sensitivity analysis for
reflows is also made in order to consider the performance of the process for changes in
operating variables.

5.5.1. Sensitivity column COLUMN-1: seen in the graph that the number of optimal
dishes of our system is 15 dishes for our separation propane vs benzene.

Figure 1. Sensitivity analysis benzene vs Propane

5.5.1.1.Sensitivity analysis reflux: it is done with the purpose of observing

which is the most optimum system concludes that there is 0.276

Figure 2. Sensitivity analysis reflux B11

5.5.2. Column sensitivity COLUMN-2

For our second column seen in the graph that the number of optimal dishes of our system
is 14 dishes for our separation propane vs Cumene

Figure 3. Sensitivity analysis vs benzene Cumene

5.5.2.1.Sensitivity analysis reflux: it is done with the purpose of observing

which is the most optimum system concludes that there is 0.512

Figure 4. Sensitivity analysis reflux B13

 5.5.3. Column sensitivity COLUMN-3

For our third column seen in the graph that the number of optimal dishes of our system is
16 dishes for our separation from Cumene vs diisopropylbenzene

Figure 5. Sensitivity analysis vs benzene Cumene

Topological TERMODINAMICA ANALYSIS FOR SEPARATION

diagram 4. Formulated distillate diagram of Cumene, Propylene Aspen plus

To analyze more afond separation of benzene and cumene vs have the separation temperature, was analyzed
in each fraction tower could go giving an example of this we diagram 3.
 diagram 5. T xy Cumene Benzene in column B13

6. results

the results of the whole process is as follows:

Material
Stream Name Units BENZENE CORRI-1 CORRI-2 CORRI-3 CORRI-4 CORRI-B1
Benze-01 kmol / h 496.901 496.901 496.901 403.587 403.587 496.901
ISOPR-01 kmol / h 0,050 0,050 0,050 86.672 86.672 0,050
PROPY-01 kmol / h 0,000 100.002 100.002 0,000 0,000 0,000
PROPA-01 kmol / h 0,050 5,048 5,048 5,048 5,048 0,050
P-DII-01 kmol / h 0,000 0,000 0,000 6,691 6,691 0,000
Stream Name Units CORRI-B2 CORRI-P DESTIL-1 DESTIL-2 DESTIL-3 FOMD-2
Benze-01 kmol / h 496.901 0,000 0,000 403.555 0,032 0,032
ISOPR-01 kmol / h 0,050 0,000 0,000 0,127 86.468 86.545
PROPY-01 kmol / h 0,000 100.002 0,000 0,000 0,000 0,000
PROPA-01 kmol / h 0,050 4,998 5,000 0,048 0,000 0,000
P-DII-01 kmol / h 0,000 0,000 0,000 0,000 0,019 6,691
Stream Name Units FOND-1 FOND-1-1 FOND-3 PROPY PURGE RECIR-1
Benze-01 kmol / h 403.587 403.587 0,000 0,000 20,178 383.378
ISOPR-01 kmol / h 86.672 86.672 0.077 0,000 0,006 0,121
PROPY-01 kmol / h 0,000 0,000 0,000 100.002 0,000 0,000
PROPA-01 kmol / hr 0,048 0,048 0,000 4,998 0,002 0,045
P-DII-01 kmol / hr 6,691 6,691 6,672 0,000 0,000 0,000

Table 1. Process results

Total energy required throughout the process and equipment.

 Power MW /
Teams
h

BOM-1 69.7904867
PUMP-1 62.6195416
COLUMN-
78.11364
1
COLUMN-
54.8204
2
COLUMN-
42.18673
3
INTER-1 78.00494
INTER-2 119.8247
INTER-3 122.7458
Interc-1 90.69779
Interc-2 157.355
MIXER-1 50.83615
MIXER-2 50.83615
REACTOR 42.17663
total 1033.11612

table 2. energy required by esquipo

7. ECONOMIC ANALYSIS OF PLANT Cumanus

Economic analysis is started in reagent costs and energy costs, in the first analysis the cost of
reagents recirculation is reduced because it has a greater impact on the overall cost of energy
(Doctrine Douglas).

To analyze the total cost of the plant is necessary to study two blocks: operating costs and cost of
reagents (benzene and propylene). First, the study of reagent costs and benefits of the sale of the
final product will be performed. For this we have used the following rates of reactants and products,
obtained by performing average price in Colombia in 2018. [14,15]

RAW MATERIAL COST

Raw materials FLOW (Kg / H) PRICE (USD / kg) COST (USD / H)
benzene 7281.9 0.5 3,640.95
propylene 4,428.54 .1639 725.837706
Total (USD / kg) 4366.78771
Total (USD / period) 34934301.6

table 3. RAW MATERIAL COST

Calculating the annual rate of the input current benzene and propylene and cumene output was
calculated taking account of a continuous operation of the plant 24 h for 333 days is 8,000
 operating hours.

Here is a summary of the costs of equipment and its installation, as well as its weight.

Component Name Total Direct Cost Equipment Cost Equipment Weight

USD USD Kg
INTER-3 97300 19500 2300
REACTOR 175700 56300 7100
Interc-1 53200 8300 160
INTER-2 146000 44500 6000
COLUMN-3 745700 214200 21890
PUMP-1 109200 62300 1700
BOM-1 115100 62600 1700
COLUMN-2 1101100 430600 55820
INTER-1 144800 39700 5200
COLUMN-1 701400 252700 28100

table 4. Equipment Cost USD

It is noted that the distillation columns are those that have higher costs, especially columns 2 benzene
separation and cumene product as might be expected.

Table breakdown of costs associated with the ancillary services shown:

description Fluid rate Units rate Units Cost per Hour cost Units
Electricity 230,08 KW KW 32.2112 USD / H
Cooling Water Toilet 1156.977 M3 M3 / H 856.16298 USD / H
Steam @ 690KPA Steam 14.99816 TON TON / H 113.536071 USD / H
Steam @ 2760KPA Steam 10.70103 TON TON / H 87.534425 USD / H

table 5. Cost per Hour

The following table lists the overall costs of the designed plant are collected, in addition to profits from product
sales. Noting this summary it can be concluded that the cost of reagents is the most impact on the total, with
the initial investment in equipment and installation which has a lower order of magnitude and therefore less
impact on the total cost.

COST
ECONOMIC EVALUATION USD / Period Percentage Percentage
RAW MATERIALS COST 34934301.6 76.72 76.72
COST UTILITIES 8,72E + 06 19.14 19.14
LABOR OPERATING COST 82240 0.18
MAINTENANCE COST 68100 0.15
OPERATING CHARGES 20560 0.05 4,13
PLANT OVERHEAD 75170 0.17
G AND A COST 716930 1,57
DEPRECIATION 919265 2,02 2,02
TOTAL EQUITY 45532126.6 USD / Period
 TOTAL EQUITY 45.5321266 USD millions /
Period

table 6. RAW MATERIAL COST

It can be seen that operating costs are those that have higher costs in the chart below.

Operational Deperciation
cost
cost 2%
4%

Utilities cost
19%

Raw materials
cost
75%

Figure 1. cost

From the cost of equipment and installation, regarded as initial investment, and the annual profit,
return on investment (ROI), which allows us to know the economic performance of the process it is
obtained.

production Flow 10398.5 Kg / h

production cost of Kg of Cumene 0.54734008 USD / KG
Work in Hours 8000 h

Commercial Sales price Cumene 1.25 USD / kg

Gross Income Margin 56.21 %

table 7. production Flow

The ROI has a very high value. Because the greatest impact on profits is due to the price of reactants
and products, and fluctuations in these prices in the market is very large.
8. conclusions

In this project I process engineering, production process cumene was designed. The parameters set
at the beginning have been met, since it has made the process simulation in addition to its economic
analysis.

The purpose of the process is obtaining the maximum conversion possible final product, since it
involves the most benefit. The simulation process has therefore been directed towards this end,
including a recycle reagent (benzene), allowing savings in raw materials, resulting in a positive
way process costs.

The reactor design was done in Matlab and des as Aspen plus 9, full utilization of the reactants, by
placing reagent limit propylene and minimizing side reaction, as there is a constant recycle of
benzene that maintains an excess of 5 1.

In the separation zone, the column layout is based on the maximum separation of the currents, thus
obtaining a product stream with about 87 kmol / h with the desired purity of 99.9% cumene per
100 kmol / h propylene and benzene introduced.

To design the process would be interesting the use of reactive distillation, as it would allow savings
in energy use and decreased equipment. This would involve replacing the assembly formed by the
main column reactor and propane by a reactive distillation column. The output product of the
reactive distillation would equally by the separation zone of benzene and cumene

In the study of economic analysis it can be concluded that the greatest weight in the total cost of
the process corresponds to the cost of raw materials. Due to price fluctuation exists, it has studied
the impact on profits of changes in the prices of both reagents and the final product, concluding
that the price of cumene is the most affect the final benefit.

BIBLIOGRAPHY

[1]. Thomas F. Degnan Jr (2001), Morris C. Smith, R. Venkat Chaya. Alkylation of Aromatics
With ethylene and propylene: Recent Developments in Commercial Processes. Applied
Catalysis A: General 221 283-294.
[2]. Industrial Organic Chemistry, Eii.Uva.Es. (2019). https://www.eii.uva.es/organica/qoi/tema-
09.php (accessed June 6 2019).

[3]. Anisimov, AV and Tarakanova, AV (2009). Oxidative desulfurization of hydrocarbon raw

materials. Russian Journal of General Chemistry 79, 1264-1273.
 [4]. Thomas F. Degnan Jr, Morris C. Smith, R. Venkat Chaya. Alkylation of Aromatics With
ethylene and propylene: Recent Developments in Commercial Processes. Applied Catalysis
A: General 221 (2001) 283-294.

[5]. PROJECT SPECIFICATIONS, Ddd.Uab.Cat. (2019).

https://ddd.uab.cat/pub/tfg/2015/133446/TFG_Arrol_part01.pdf (accessed June 6 2019).

[6]. Iliyan Kolev, Vesselina Mavrodinova, Magdolna R. Mihályi, Márton Kollar, Comparative
studies on alkylaromatics catalytic transformations over [Al] MCM-22 and boron-Substituted
[Al, B] MCM-22, Microporous and Mesoporous Materials, Volume 118, Issues 1 -3, 2009,
Pages 258-266, ISSN 1387-1811

[7]. A. Corma, catalysis with zeolites: from the laboratory to industrial application, ARBOR
Science, thought and culture. (2011) 83-102.
.

[8]. S. Nikfar, AF Behboudi, Cumene, Editor (s): Philip Wexler, Encyclopedia of Toxicology
(Third Edition), Academic Press, 2014, Pages 1082-1085, ISBN 9780123864550

[9]. Lv J., L. Chen, W. Chen, H. Gao, M. Peng, Kinetic analysis and self-accelerating
decomposition temperature (SADT) of dicumyl peroxide, Thermochim. Acta 571 (2013) 60-
63.

[10]. Ilaria Di Somma, Raffaele Marotta, Roberto Andreozzi, Vincenzo Caprio, Detailed
thermal and kinetic modeling of cumene hydroperoxide decomposition in cumene, Process
Safety and Environmental Protection, Volume 91, Issue 4, 2013, Pages 262-268, ISSN 0957-
5820

[11]. PLANT LOCATION, Frro.Utn. (2019).

https://www.frro.utn.edu.ar/repositorio/catedras/quimica/5_anio/integracion5/seccion2.pdf
(accessed 7 June 2019).

[12]. CEPSA, Cepsa.Com. (2019).

https://www.cepsa.com/stfls/corporativo/FICHEROS/infografia-shanghai-ESP.pdf (accessed
7 June 2019).

[13]. roads | Municipality of Barrancabermeja, Barrancabermeja.Gov.Co. (2019).

https://www.barrancabermeja.gov.co/v%C3%ADas (accessed 7 June 2019).

[14]. Abánades, J. (2019). MODEL RADFRAC distillation column. [Online]

Diquima.upm.es. Available at:
http://www.diquima.upm.es/old_diquima/recursos/aspen/radfrac.html [Accessed June 14,
2019.].

[15]. Natural, G. (2019). grupovanti. [Online] grupovanti. Available at:

https://www.grupovanti.com/co/1285085318259/inicio.html [Accessed July 7, 2019.].
[16]. ICIS Pricing (Independent Chemical Information Service). Available January 11,
2017. http://www.icis.com/chemicals/

[17]. S & P Global Platts. economic analysis of raw materials worldwide. Available
January 11, 2017.http: //www.platts.com/news-feature/2018