CHAPTER 1 FEASIBILITY STUDY.pdf

8/17/2019 CHAPTER 1 FEASIBILITY STUDY.pdf

http://slidepdf.com/reader/full/chapter-1-feasibility-studypdf 1/41

1-1

CHAPTER 1

FEASIBILITY STUDY

1.1 PROCESS BACKGROUND AND SELECTION

1.1.1. INTRODUCTION

Table 1.1 Physical properties of 2-Ethylhexyl Acrylate

colourless liquid with a sharp and musty odour

Purity 99.5%

Melting point -90°C

Boiling point 213-218°C

Density 0.887 g/ml at 20°C

Vapor pressure 0.14 mmHg (19 Pa) at 20°C

Flash point(The institute of food safety and

toxicology)

82-92°C at open cup86°C at close cup

Source:(http://ecb.jrc.ec.europa.eu/documents/Existing-

Chemicals/RISK_ASSESSMENT/SUMMARY/2ehasum058.pdf)

In Malaysia, the BPC Acrylics Complex located in Gebeng, Pahang, was

developed under a joint venture between BASF AG and Petronas to produce 160,000

Tonne per annum Crude Acrylics Acid, 20,000 tonnes per annum Glacial Acrylic Acids,

100,000 tonnes per annum Butyl-Acrylate and 60,000 tonnes per annum 2-Ethyl Hexyl

Acrylate which has existed at 2000. (Rainhill.com).

2-Ethylhexyl acrylate is used as a monomer in the chemical industry for the

production of polymers and copolymers, which are mainly processed further to aqueous

polymer dispersions. The polymers and polymer dispersions are used in adhesives and

http://ecb.jrc.ec.europa.eu/documents/Existing-Chemicals/RISK_ASSESSMENT/SUMMARY/2ehasum058.pdf






1-3

1.1.2. PROCESS CHEMISTRY

2-Ethylhexyl Acrylate is an organic compound of an ester group. The general structural

formula of an ester is given by

Figure 1.2 General structure formula of an ester

An ester is produced by esterification process from the reaction of a carboxylic

acid and an alcohol. Through this process, typically esters will be formed together with

water. Specifically, when 2-ethylhexyl acrylate is to be produced, sulfonic type of

catalyst is used with strong acid as a catalyst. The presence of the catalyst is to

promote satisfactory rate of production. The reaction is equilibrium and reversible,

where the reverse reaction is an acid hydrolysis of esters. Hydrogen ion from the

catalyst catalyzes the forward reaction, which is esterification. This hydrogen ion also

catalyzes the reverse reaction, which is hydrolysis. As a non-ideal equilibrium, the type

and ratio of reactants, temperature and water affect the equilibrium. The process is also

characterized by high yield of production, where the yield can be achieved up to 98%.

1.1.3. REACTION MECHANISM

Acrylic acid contains the carbonyl group, C=O. This group is retained in the product

while acrylic acid undergoes the esterification process and does not suffer any

permanent changes itself. On the other hand, the hydroxyl group in the acid which is -

OH group undergoes nucleophilic substitution as the acid reacts with the alcohol.

Providing site for this nucleophilic attack is one of the functions of the carbonyl group in

this case. Since the acid-catalyzed esterification of a carboxylic acid with an alcohol is

reversible, the reverse reaction will then have the same mechanism in its respective

direction.



1-4

Thus, any evidence about one reaction must apply to both. The acid-catalyst

speeds up both processes by protonating carbonyl oxygen and thus rendering carbonyl

carbon more susceptible to nucleophilic attack. In esterification, the nucleophilic is an

alcohol and the leaving group is water. In the process, there is almost certainly a

tetrahedral intermediate, or rather, several of them. The existence of more than one

intermediate is required by, among other things, the reversible nature of the reaction.

The intermediate in esterification almost certainly must be involved, since it is the

product of attack by alcohol on the protonated acid. The mechanism for acid catalyzed

Hydrolysis and esterification is shown in Figure 1.3.

+H-

- H-

H5C6

O

OH

H

H5C6

O+

OH

+CH3 --- OH

-CH3--OH

CH3

O

H

H5C6

O

OH H

The carboxylic acidaccepts a proton from thestrong acid catalyst

The alcohol attacks theprotonated carbonyl groupto give a tetrahedralintermediate

a proton is lost at oneoxygen atom and gainedat another

CH3

O

H

H5C6

O

OH H

-H2O

+ H2OCH3

H

H5C6

O+

O

-H-

+ H -

CH3H5C6

O

O

Loss of a molecule ofwater gives a protonated

ester

Transfer of a proton to a

base leads to the ester

Figure 1.3 The reaction mechanism of acid catalyze hydrolysis & esterification

As mentioned earlier, 2-ethylhexyl Acrylate is produced by direct esterification

process. This process is the most common process for producing 2-ethylhexyl acrylate

on a commercial scale and the process can be either continuous or batch.

1.1.4. PROCESS BACKGROUND

Esters of acids are important from the industrial standpoint as a great variety of

commercial products are based on such esters. The two classical methods of preparing

the esters are by direct esterification and transesterification.



1-5

1.1.4.1. Direct Esterification

2-Ethylhexyl Acrylate is formed by direct esterification of Acrylic Acid with 2-

Ethylhexanol which occur in the liquid phase. In Ullman’s Encyclopedia of Industrial

Chemistry, 1999, esterification describes processes for the preparation of higher and

lower alkyl acrylates by acid-catalyzed esterification of acrylic acid with the

corresponding alcohol in the presence of an acidic catalyst, in which distillation columns

in the working-up of the reaction mixture operated under reduced pressure in order to

be able to reduce the distillation temperature. In which, the polymerizable compounds

are exposed is desirable since the danger of polymerization generally increases with

increasing temperature. The liquid ring pumps in which are the vacuum pump is used

for generating a vacuum pressure in the system.

The reaction between these two components occurs at a rule 70-150 oC in which

preferably 80-130 oC. In the first reaction, it is preferably 100-160 oC and 110-130 oC for

the last region. (Nestler et.al., 2004) and using sulfonic acid type of catalyst. The

reaction temperature is preferably established so that it increases along the cascade.

The formation reaction of 2-Ethylhexyl Acrylate is a reversible process, exothermic and

equilibrium process. The yield of 2-Ethylhexyl Acrylate, based on Acrylic Acid can be

achieved about 91-98% depending on the ester and reaction conditions (John J.

Mcketta, Volume 1, 1983). At molar 2-Ethylhexanol excess as low as 4.4%, the purity of2-Ethylhexyl Acrylate is practically 99.5% (John J. Mcketta, Volume 1, 1983). In this

process, there are by-products formation due to impurities of raw material used which is

acrylic acid.

O

OH

CH2

+ CH

C2H5

H9C4 CH2OH

CH3

O

OCH2CH C4H9

C2H5

+ OH2

Figure 1.4 Reaction of 2-Ethylhexyl Acrylate

The esterification takes place in a reaction zone in a homogeneous, liquid phase

at elevated temperature by reaction of acrylic acid with 2-ethylhexyl alcohol in a molar

ratio of 1:0.75 to 1:2, preferably from 1:0.9 to 1:11, to be particularly 1:1. (Nestler et.al.,



1-6

2004), The acrylic acid, alcohol and acid catalyst are fed to the reaction zone and the

water formed is separated off by rectification during residence time as part of mixture

comprising starting alcohol via top column attach to the reaction zone.

1.1.4.2. Transesterification

Ethyl Acrylate reacted with 2-ethylhexanol to form 2-ethylhexyl Acrylate and Ethanol by

transesterification which exchange of alcohol groups known as alcoholysis. In order to

promote the reaction, transesterification can be conducted with both heterogenous acid

and base catalyst. Potassium cyanide which is base catalyst was recommended to

accelerate the reaction but the yields are correspondingly lowered.

For acid catalyst, titanium acid ester was choosed because it is pre-dominantly

used on an industrial scale. Titanium esters must be hydrolyzed into insoluble

substances before they can be separated from the reaction mixture. This can be

accomplished by the treatment with caustic soda. Yield of 2-Ethylhexyl acrylates are

higher than using base catalyst. The reactants and catalyst will both react in reactor

vessel with temperatures near 100oC. Transesterification of Ethyl Acrylate with alcohols

in the presence of acidic or basic catalysts gave the corresponding higher esters in

good yield (Kirk othmer, 2007).

1.1.5. PROCESS SELECTION

In this design project, ‘direct esterification’ was choose as routes for the production of 2-

Ethylhexyl Acrylate by using Acrylic acid and 2-ethylhexanol as the raw material while

the sulfonic acid type catalyst is para-toluene sulfonic acid.

The selected process is chosen base on a few factors. The most important

factor is to limit the production and operation cost. When compared the price of the raw

materials of processes the most expensive raw materials is acrylic acid but the price of

2-Ethylhexyl Acrylate is relatively high, therefore, short years is needed to achieve the

break –even market (ICIS.com). However, from the overall expenses in material such as

raw material and catalyst, transesterification process is far more expensive than direct



1-7

esterification because of titanium catalyst price. Even though the expensive raw

material is chosen, the percentage conversion is still higher.

Furthermore, the availability of Acrylic Acid is more variety and closes to the site

compare to Ethyl Acrylate which is only in Kerteh, Terengganu. In other way, it will cut

off some of the expenses for raw materials transportation since the raw material is

expensive enough, the supplier location needs to be closer to prevent any unnecessary

flow of funds in transportation. In addition, the time consumes to send the supply is

shorter because time consuming means loss of money.

Through this decade, most company uses processing of 2-Ethylhexyl Acrylate

by direct esterification routes of Acrylic Acid. This does mean that it is the most

commercial process used in industries these days and it has been established. Whereelse, transesterification process of esters is still theoretical proven. Many researches

are still doing in improvising transesterification process.

Last of all, by using this process the energy use and release are lesser than

transesterification. The process to break up and forming of the bonds are easy for

Acrylic Acid and 2-Ethylhexanol than Ethyl Acrylate because the breakage occurred at

oxygen bonding with hydrogen molecules compare to oxygen bond with C –C

compound. This advantage will give the plant less energy release as well as the cost foroperating the utilities systems to cool down or heat up the process.

Table 1.2 below shows the summary of the factors that included in the process

of selection and the according marks for each.

Table 1.2 Summary of process selection

Factors WeightageDirect

EsterificationTransesterification

Raw material supply 8 8 2

Cost of raw material 10 5 8

Availability of material 8 8 2

Energy release 6 5 3

Commercialize 4 4 2

Total 36 30 17



1-8

Therefore, from the previous Table 1.1, the direct esterification method was

chosen due to its attractive advantages compare to transesterification process. For a

route to be commercially attractive, the raw material costs and utilization must be low,

plant investment and operating cost not excessive, and waste disposal charges minimal

(Encyclopedia of chemical processing and design, Volume 10). The justification on

each weightage has been explained in this early chapter.

1.1.5.1. Process Details Descriptions

The esterification reaction for reacting 2-ethylhexanol and acrylic acid in a molar ratio of

1.1:1 (Patterson et. al., 1999) was carried out in an esterification reactor 1 at 110°C with

the pressure of 0.29 bar (Patterson et. al., 2009). The conversion for the process is

80% (BASF & Patterson et. al., 2009). Two esterification reactors were used in this

process. The esterification reactor 1 is set with 59 % conversion, whereby the

esterification reactor 2 is set with 21% conversion. The two esterification reactors in a

cascade arrangement are use with each having utilizable capacity of 2:1 (Iffland et. al.,

1999). The liquid output stream of one reaction region here forms the feed to the

downstream reaction region which occur by means of overflow. The product in the

vapor phase form is transferred to the water removal column where the water of

esterification produce from the reaction is being removed. The water removal column is

needed in order to bring the main reaction forward which is according to the Le

Chatelier principles whereby, 1 mol of reacted equals to 1 mol of product is produce.

The bottom product discharged from the first reactor was fed into the second reactor

which also operated at 0.29 bar at 120°C.

The liquid discharge from the second reactor is fed into the lower part of heavy

product recovery column which was configured as an enrichment column and, being

fitted with ten dual flow trays (Iffland et. al., 1999 & Nester et al, 2004). The head and

bottom pressure operated at 0.04 bar and 0.11 bar, where as the base temperature

operated at 130°C. A liquid stream recovered from the base column was fed to the

cracking unit, whereby high boiler is remove and sent to the central boilers. The

cracking recovery which consists of product is use as a bottom feed for the EHA

recovery column.



1-9

The EHA recovery column was operated at a bottom pressure of 0.07 bar and

top pressure of 0.02 bar. The column is fitted with 25 dual flow trays (Nestler et al,

2004). The temperature of the base column was 122°C. The product is recovered at the

bottom stream at 90 % purity (Patterson et. al., 2009. The distillate is recycling to the

water removal column. Pure product of 2-EHA was taken off in liquid form and cooled to

20°C in order to avoid color number problems and to make possible the change in

stabilization of the product from phenothiazine as process inhibitor to hydroquinone

monomethyl ether as storage stabilizer. The phenothiazine used as process inhibitor

was fed to the tops of the heavy product and product recovery stream

1.1.5.2. Block Flow Diagram

Figure 1.5 Block flow diagram of production of 2-EHA

Raw material such as acrylic acid & catalyst are fed to the first reaction region

where else, 2-ethylhexanol was fed to the absorber. The current invention is that the

absorber was connected with the reactor 1 in order to remove water as it has form in

the reactor 1. However, the removal of water can be carried out by addition of an

organic solvent as azeotropic entrainer. The use of 2-ethylhexanol at excess can also

serve as azeotropic entrainer. In another variant, the water is distillatively remove as



1-10

constituent of an azeotrope comprising product/2-ethylhexanol/water and containing

more than 95% by weight of water. The liquid from reactor 1 is overflow to the reactor 2

in order to extend the residence time of reaction in order to form more product. The

liquid outlet from reactor 2 is fed to the heavy removal column in order to remove heavy

compound which has higher boiling point than the product. The heavy stream which

contains trace of reactant & product is recovered in the cracking unit before discharge

to the incinerator. The recovered reactant & product with the distillate of the heavy

column is fed to the product refining column to purify the product whereby the

separation of the product from the reactant.

1.1.5.3. Process Equipment

Table 1.3 belows describe the function of the equipment used in the production of 2-EHA.

Table 1.3 The equipment used in the production of 2-EHA

Equipments Functions

Esterification reactor 1

To hold the reaction process &

provide a fairly large reservoir of

reactants, product & water for water

removal column

Esterification reactor 2To extend the residence time of

main reaction process

Water removal column

To remove the water which

generated from esterification

reaction

Heavy components

removal

To remove the heavy component

from the stream

Product refining columnTo separate the reactant from the

product

Process heaters,

condensers, and coolers

To provide the heating and cooling

required by the process



1-11

1.1.5.4. Reaction Kinetics

Synthesis of 2-Ethylhexyl Acrylate from Acrylic acid and 2-ethylhexanol and catalyzed

by para-toluene Sulfonic acid is a reversible esterification. Therefore, by removing water

of esterification, the reaction can be moves forwards. According to the Le Chatelier

principles, 1 mole of reactant converted, 1 mol of product produce.

C3H4O2 + C8H18O ↔ C11H20O2 + H2O

The side reactions that are considered in 2-ethylhexyl acrylate production process is

given as follows.

A) Dimerization of the Acrylic Acid

From the article from BASF, September 2010, the diacrylic acid formation begins

spontaneously upon acrylic acid production. The reaction cannot be chemically inhibited

or reversed. Since both water concentration and temperature impact the rate of DAA

formation, the rate can be minimized by controlling the temperature of the acrylic acid

and excluding moisture. The presence of DAA in acrylic acid that is processed to

produce higher value added materials can adversely affect the final product.

The possibilities include yield reduction, molecular weight variation, residual

impurity concentration, processing problems and product performance variations.

Based on experimental kinetic studies, diacrylic acid is formed by a second order

reaction involving the conjugate addition of a nucleophilic species to the electrophilic

double bond (Michael Addition Reaction).

The mechanism of dimerization process is as follows:



1-12

Figure 1.6 The mechanism of dimerization process

Therefore, as a result of acetic acid that exists as the impurity in the acrylic acid

reacted with 2-ethylhexanol producing Diacrylic acid, Octenes and water. Octyl

propionate is considered as the heavy product since it has high boiling point than 2-

EHA product.

2C2H4O2 + C8H18O → C6H8O4 + C8H16 + H2O

B) Formation Of Ethylhexyl Acetate

C2H4O2 + C8H18O → C10H20O2 + H20

Ethyl hexyl acetate formed when acetic acid and 2-ethylhexanol react. The raw

material, Acrylic Acid consist the impurity of 0.5% of acetic acid. Ethyl hexyl acetate is

considered as the light end for the process since its low boiling point compare to the

product.

C) Formation Of Octyl Propionate

C3H6O2 + C8H18O → C11H22O2 + H2O

Octyl propionate and water is also formed when propionic acid that existed in the

acrylic acid as the impurity reacted with 2-ethylhexanol. It is considered as the heavy

key due to its high boiling boiling point higher than EHA.



1-13

The formation of by-product can be minimize or eliminated if the reactants

impurity are controlled to contain low concentrations of formic acid, propionic acid and

isobutanol. If the feeds have low enough contaminants, the by-products reactions will

be eliminated. Finally, the reverse reaction of the esterification reaction can be avoided

if the products formed in the reactor are removed continuously from the mixture. Once

they are removed, the chance for the hydrolysis reaction to occur is very limited.

1.1.6. CATALYST

It has long been known that mineral acids greatly increase the rate of esterification. The

most commonly used mineral acid is probably sulfuric acid. The catalyst used in Direct

Esterification process is sulfuric acid. It is effective and not as corrosive to metals ashydrogen chloride. Close control is required since even modest increase in

concentration or temperature can cause dehydration of alcohols to ether or olefins.

Problems with formation of color bodies may also be a concern. Concentrations of from

a few tenths to 1 or 2 % by weight are generally employed. (Kirk Othmer, 2007)

In this process, para-toluene sulfonic acid is use since it has good catalytic

activity and generally causes fewer side reactions than sulfuric acid. A little higher

concentration of the sulfonic acid may require in order achieving the same reaction rate

that can be obtained with a given quantity of sulfuric acid. (Kirk Othmer, 2007).

1.1.7. CHARACTERISTIC USE FOR PROCESS ROUTE SELECTION

1.1.7.1. Safety Of The Plant

The reaction of Direct Esterification proceeds are the temperature equivalent to the

boiling point of the liquid mixture in the column. So, the temperature control is simpleand reliable towards the process. The primary reactor design is maximized the degree

of reaction in the simplest equipment. Hence, this plant is safe due to its physical

conditions such as low temperature, low pressure and simplest equipment used.

(www.arkema-inc.com/literature/pdf/405.pdf)

http://www.arkema-inc.com/literature/pdf/405.pdf





1-14

1.1.7.2. Economical

These plant is reduce in capital cost because do not required many equipment. Its

products yield can achieved high purity of 2-EHA which is up to 96%. The reactant

recovery distillation column act as the reactant recovery which is will be recycle to thereactor. This is one of the economical strategy by maximize the usage of the reactants.

In fact, it will minimize the waste stream produce from the process, therefore, it will

minimize the cost for waste treatment.

1.1.7.3. Minimum Waste Or By Product

From the process used, there are minimum by-product will be converted. As a result by

using para-toluene sulfonic acid, it causes fewer side reactions since it has good

catalytic activity (Kirk Othmer, 2007). The unreacted reactant material such 2-

ethylhexanol and acrylic acid will be recycle to the reactor back as a recovery stream.

The light impurities, heavy impurities and aqueous solution was sent to waste

treatment. Amount of wastes produces is also in small percentage and which require to

sent to waste treatment. The volatile and heavy component was sent to the central

boiler for treatment. (www.arkema-inc.com/literature/pdf/405.pdf )

1.1.8. PROCESS ROUTE SELECTIONS

2-ethylhexyl acrylate is the most widely produced by esterification of alcohol and

carboxylic acid. In the improved of esterification process of the present invention, the

alcohol is employed in an excess over that stoichiometrically required to react with the

acid. Accordingly, the molar ratio of alcohol to carboxylic acid will be greater than 1:1,

and amounts up to about 4:1 may be employed. More desirably, the amount of alcohol

employed will lie in the range of about 1.2 to 3 moles of alcohol per mole of acid with

about 1. 5 to 2.0 moles of alcohol to mole of acid being most preferred.

The raw materials that used to produce 2-etylhexyl acrylate are acrylic acid and

2-ethylhexanol. Acrylic acid is used as a precursor for a wide variety of chemicals in the







1-15

polymers and textile industries. There are several choices for the production of the raw

materials which are:

Production of 2-EHA by producing Acrylic acid from Propylene

Production of 2-EHA by producing 2-Ethylhexanol from Propylene

Production of 2-EHA by using Crude Acrylic Acid & 2-ethylhexanol buy from other

manufacturer

1.1.8.1. Production Of 2-Ethylhexyl Acrylate By Producing Acrylic Acid From

Propylene

This recently developed process involves the oxidation of propylene to

hydroxypropionic acid. Nitric acid acts as a catalyst for the reaction. Subsequent

dehydration of this process will yields acrylic acid. The stepwise representation can be

shown as follows:

+ O2 CH3 CHOHCOOH CH2 CHCOOH + OH2H3CHC CH2

propylene oxygen Hydroxypropionic acid acrylic acid

An alternative route is the catalytic oxidation to acrolein, CH2CHCHO, and then to

acrylic acid with presence of oxygen and certain metallic catalyst.

1.1.8.2. Production Of 2-Ethylhexyl Acrylate By Producing 2-Ethylhexanol From

Propylene

This recently developed process involves the oxidation of propylene to n-butyraldehyde

and iso-butyraldehyde. The catalyst used is rhodium catalyst. 2-Ethylhexanol produced

via this sequence reaction of aldolization, dehydration and hydrogenation from n-

butyraldehyde. The reaction stoichiometry is given below:



1-16

2CH3CH2CH2CHO H3CH2CH2C CHCHCHO

CH2

H3

C

H2O

H3CH2CH2CHC CCHO

CH2

H2

H3

C

CH3CH2CH2CH2CHCH 2OH

CH2

H3

C

Figure 1.7 Mechanism of producing 2-ethylhexanol by propylene



1-17

Table 1.4 Comparison Of Process Route Selection

Starting Route Advantages Disadvantages

Propylene

(to produce Acrylic

Acid)

i. Relatively low cost of propylene

ii. Availability of highly active and selective

catalyst

iii. Produce high quality of 2-ethylhexyl

acrylate

i. Cost of equipment is expensive and it

involves of two stage reactor.

ii. Formation of intermediate and by-

product

iii. Cost of catalyst used for eliminates

acrolein (intermediate) is around

$2.25/kg

Propylene

(to produce 2-

Ethylhexanol)

i. Low cost of propylene

ii. Low feedstock and energy requirements

iii. Low maintenance requirements and low

environmental impact.

iv. Low by-product formation

i. Cost of equipment is expensive and it

used 2 reaction reactor and 3

separation equipment.

ii. Formation of intermediate and by-

product

iii. It needs really carefully when handle

this material because irritates skin, eyes

and respiratory tract.

iv. Estimation of raw material cost is RM

1,408.92/tonne

v. Some of the raw material is hard to find

in Malaysia.

Local market

(bought acrylic acid

and 2-ethylhexanol)

i. There is no need for another process to

produce the raw material

ii. There are nearer supplier to provide the

material

iii. The cost of equipment is cheaper

compare to produce the raw material

i. The supplier also produces the product

2-Ethylhexyl acrylate.

ii. The raw material cost is slightly higher

from raw material producing 2-

ethylhexanol and acrylic acid



1-18

Table 1.5 Summary of comparison

Various methods for the manufacturer of 2-Ethylhexyl acrylate are mentioned

above. Table 1.4 shown the advantages and disadvantages of the methods and Table

1.5 is the summary of table 1.4 to show it more clearly about the factors were

considered in order to choose the best method to produce 2-Ethylhexyl Acrylate. From

the table 2 above, it shows that each of the factors will be given 5 marks. Local market

for Acrylic acid and 2-Ethylhexanol is the best choice to produce 2-Ethylhexyl Acrylate

because it has more advantages.

For a route to be commercially attractive the raw material costs and utilization

must be low, plant investment and operating cost not excessive, and waste disposal

charges minimal.

1.1.9. PROCESSING FLOW SELECTION BASED ON PATENT INVENTION

1.1.9.1. Esterification of Acrylic Acid and 2-Ethylhexanol by Using Solvent (US

PATENT: 0192957 A1, Wickens et. al.,2004)

Acrylic Acid rich feedstock and fresh 2-Ethylhexanol from storage is combined

with recycle 2-Ethylhexanol from the distillation column of 2-Ethylhexyl Acrylate unit and

Factors PercentagePropylene

(Acrylic Acid)

Propylene

(2-Ethylhexanol)

Local Market

Crude Acrylic

Acid

Supplier of rawmaterial

5 3 3 5

Safety

consideration5 4 4 4

Using high

technology5 5 5 5

Initial set up cost 5 3 2 5

Widely used in

industry5 5 3 5

Environmental

effect5 3 3 4

Total 30 23 20 28



1-19

fed to the reactor with catalyst Sulphuric Acid. Acrylic Acid and 2-Ethylhexanol (molar

ratio acrylic acid:2-Ethylhexanol = 1:1) is fed to the reactor. The reaction condition is

exothermic and occurred at 90oC. Normally, the pressure is above atmospheric

pressure to remain in liquid phase. After reaction, the product is pumped to the

extraction column and washed with water to remove organic phase at the top while at

the bottom, to remove is aqueous phase.

The organic phase then being sends to the distillation column. Top products

obtained from separation are Acrylic Acid and 2-ethylhexanol which recycle to the

reactor. The bottom product, 2-Ethylhexyl Acrylate being send to distillation column and

emerges at the top, purified from heavy products. Aqueous phase result from extraction

column undergoes hydrolysis. Adding of NaOH required in order neutralizing the

Sulfuric Acid. 2-EthylHexanol obtained from hydrolysis process being distillated atdistillation column and recycle to reactor. Waste water in the form of aqueous phase is

send for further treatment.

Table 1.6 The advantages & disadvantages of producing 2-EHA by addition of solvent

Advantages Disadvantages

High purity of product yields

All reactant left over is recover

during the process

Too many main equipment used

will cause highly fixed capital cost

Too many waste water stream will

cause large volume of reactant is

converted into waste.

High COD and BOD level of

wastewater due to the use of

NaOH to neutralize the sulphuric

acid

Highly corrosive catalyst is used,

there is a need to spend on highly

cost sheeting inside the reactors

Low yield of product due to sulfuric

acid catalyst used.



1-20

By referring to this process, there will be more waste stream produce, too many

equipment used which refer to not economical & highly corrosive catalyst are used.

Therefore, this processing flow is not chosen.

1.1.9.2. Esterification of Acrylic Acid and 2-Ethylhexanol Without Using Solvent(US PATENT: 5883288, Iffland et al, 1999)

By referring to the PFD, the advantages and disadvantages of the process as describe

in Table 1.7 follows.

Table 1.7 Advantages & disadvantages of the production of 2-EHA without addition ofexternal solvent.

Advantages Disadvantages

Less major equipment will decrease the fixed

capital cost invested

Less corrosive para-toluene sulfonic acid catalyst

is use which can be regenerated

Catalyst use will produce high yield of the product

Less waste stream generated

Operating pressure under vacuum, decrease the

operating temperature since polymeriazation

occur at high temperature.

Basf company current process use

(commercialization)

High purchasing cost

of individual

equipment such as

reactors.

Expensive catalyst

use

Therefore, this process is comparatively reliable compare to the previous process. In

that case, this processing flow from this patent was chosen for the production of 2-EHA.



1-21

1.1.10. CONCLUSIONS

This chapter is mainly use to determine & verify the most suitable process that is

compatible with the safety, economical & environment. The criteria involves are well

described such as the process background, reaction kinetics, process description,

process selection, catalyst used and etc in order to help gain more understanding of the

process. The commercial direct esterification process was chosen as the process

selection. The raw material use in the process will be brought from the potential supplier

in order to limit the cost of production. Less waste stream is to be generated with the

current process route selection and less side product is produce with the use of para-

toluene sulfonic acid liquid catalyst which is also can be regenerated. Major equipments

function use in this processing plant also has been identified. The side reaction due to

the impurity of reactant to be considered in this plant also has been highlighted here.

1.2. MARKET ANALYSIS AND DEMAND

1.2.1. GLOBAL DEMAND AND SUPPLY

This market analysis consists of demand of 2-Ethylhexyl Acrylate (2-EHA) to

ensure whether there are demands for it and shortage of the production. This willensure 2-Ethylhexyl Acrylate produce from this plant have buyers.

According to ICIS, the demand for 2-Ethylhexyl Acrylate for previous years is not

stable due the shortage of raw material supply which is Acrylic acid importantly and 2-

Ethylhexanol. Even though the demand is not stable but the usage of 2-Ethylhexyl

Acrylate is wide. The industries used 2-Ethylhexyl Acrylate are coatings, adhesives and

in textiles and fibers. Globally, coatings were the largest application of 2-Ethylhexyl

Acrylate accounting for about 50% of demand in 2007 reported Sahara PetrochemicalCompany.

Correspond to Sahara Petrochemical Company, the next largest applications

were adhesives (22%) and textiles and fibers, which accounted for about 22% and 15%

of demand respectively. In early 2010, the forecast of the demand for commodity



1-22

Acrylates which is 2-Ethylhexyl Acrylate will grow at 3.7%/year from 2009, the year of 2-

Ethylhexyl Acrylates recession. The demand is higher but the supply is limited globally,

hence the price can be rise up by month to month. The major world demand in 2007 of

2-Ethylhexyl Acrylate are Western Europe, USA, Japan, China, rest of Asia and Middle

East/ Africa as shown in figure 2.1. Both China and rest of Asia together accounted for

38.8% of the global demand.

Figure 1.8 Global demand of 2-Ethylhexyl Acrylate

Table 1.9 below is the trend data for global demand of 2-Ethylhexyl Acrylate

According to the Table 1.9, Asia demand keep increasing and demand in Europe keep

decreasing. In global demand forecast, Asia region will lead the demand of 2-Ethylhexyl

Acrylate because increasing usage of paint and textiles.

21%

28%

1%

8%

14%

25%

3%

Global Demand for 2-Ethylhexyl Acrylate in

2007

US

Western Europe

Eastern EuropeJapan

China

Rest of Asia

Middle East/Africa



1-23

Table 1.8 Trend of World demand by Region

Region2-Ethylhexyl Acrylate (MT)

2005 2006 2007

US 115 000 118 000 122 000

Western Europe 154 000 157 000 160 000

Eastern Europe 3 000 3 000 4 000

Japan 48 000 48 000 49 000

China 71 000 75 000 79 000

Rest of Asia 132 000 138 000 144 000

Middle East/Africa 16 000 17 000 17 000

Sources: Sahara Petrochemical, 2009

1.2.2. OVERVIEW OF GLOBAL SUPPLY

During the past few years, global capacity of commodity Acrylates including 2-

Ethylhexyl Acrylate is grew rapidly. According to the following Table 1.10, China

reported the largest increase in production capacity of 2-Ethylhexyl Acrylate, United

States continues to be the dominant producer of Acrylate but Market forecast has made

and it shows Asia will overtaken United State in 2012 or earlier than predicted.

Table 1.9 Global Capacity by regions in 2009 and forecast 2012

RegionCapacity (MT)

2009 2012

US 155 000 155 000

Western Europe 95 000 95 000

Eastern Europe 950 950

Japan 108 000 108 000China 140 000 200 000

Rest of Asia 85 000 115 000

Sources: Market analysis Orbichem , 2007

http://www.saharapcc.com/English/MediaRelations/Publications/Documents/SAHARA

http://www.saharapcc.com/English/MediaRelations/Publications/Documents/SAHARA



1-24

1.2.3. ASIA MARKET AND DEMAND

According to SunVic Chemical Holdings Limited Annual Report 2006, Figure 2.2 below

shows the Acrylic Acid (AA) and Acrylate Esters (AE) Capacity growth. Focusing onlyon the AE capacity growth, it can be said the growth increase continuously with time. By

looking for the increasing of demand by the global market that discuss before, it can be

concluded that the growth and demand for AE will increase throughout this year. By

referring to the figure 2.3, it shows that the demand for end users of Acrylic Acid (AA)

and Acrylate Ester (AE) which based on 2002 sales in Asia.

Figure 1.9 Acrylic Acid and Acrylic Esters Capacity Growth

Figure 1.10 AA and AE end uses in Asia (SunVic Chemical Holdings Limited Annual Report 2006)



1-25

1.2.4. MALAYSIA DEMAND OF 2-ETHYLHEXYL ACRYLATE

As previously explained, the world demand for 2-Ethylhexyl Acrylate is increasing for

this second trimester of this year. This is due to the limiting feedstock whereby the

major of the plant in Europe is trying to find sources from the Asia region although it

also curtailing in China which is the major producer of 2-Ethylhexyl Acrylate. This

phenomenon wills also increased the demand in Malaysia. Since larger company will fill

up the world demand, therefore, processing the 2-Ethylhexyl Acrylate by this plant will

meet up the demand in Malaysia and global.

In Malaysia, 2-Ethylhexyl Acrylate was used in consumer needs products and

industrial needs such as paint, textiles, and adhesives. Corresponds with Malaysia as

developing country, a Malaysian lifestyle is also developed towards better life. Hence,they need more textiles for fashion, paint for decoration part and coating for industries,

with this it will increase the demand of 2-Ethylhexyl Acrylate in this developing country.

1.2.4.1. Selling Price in Asia and Malaysia

The selling price is important for the product in which mean to identify the pattern of

product price to be sold to the customer. This plant need to sell at the lower price ones

can offer or same as current market price. The selling price needs to make profit atleast in 5 to 7 years. In Malaysia, the selling price of 2-EHA according to BASF-

Petronas company is RM 3,879.51/tonne.



1-26

Figure 1.11 Trend selling price in Asia January-May, 2009 and 2010Source: Department of Statistics Malaysia, 2010

According to figure 1.11, it shown that the selling price is increasing sharply from

2009 to 2010. It means that, demand of 2-Ethylhexyl Acrylate is growing and produce

this material will make a profit because the market price of the world also increase.

According to forecast, this selling price will increased.

1.2.4.2. Potential Buyers in Malaysia

Nippon Paints (Paint application)

KCC Paints

Vital Technical Sdn. Bhd.

Seamaster

Federal Paints Manufacturing (M) Sdn Bhd

National Lacquer & Paint Products Co (M) Sdn Bhd

Jotun (M) Sdn Bhd Rivertex (Adhesives)

These potential buyers are stable company in Malaysia. With this plant strategy, more

company will buy the product.

0

1

2

3

4

56

7

8

9

china singapore indonesia india taiwan japan

P r i c e R M / k g

)

Country

Selling Price Trend of 2-EHA

2009

2010



1-27

1.2.5. CONCLUSION

From literature review, market prospect for 2-Ethylhexyl Acrylate is very broad because

the usage of 2-Ethylhexyl Acrylate is the need of consumer. Hence, 2-Ethylhexyl

Acrylate will always be in the market. In addition, the properties of 2-Ethylhexyl Acrylatewhich is less hazardous than other monomer is the attraction to the manufacturer

change direction to it. Even though, every month the selling price is increasing because

of the recession of 2-Ethylhexyl Acrylate on 2009, the demand is still increasing. The

demand is increasing in global and in Malaysia itself as well. In Malaysia, there are

buyers that will buy the product because in global and Malaysia, they are short of this

material. The budget given which is RM 200 Million is enough for the construction of the

plant not including the operational cost. With the cost, the plant should be build and it is

feasible enough.

1.3. SITE SELECTION AND PLANT LOCATION

1.3.1. INTRODUCTION

Location decision is essential since they are long term choice and require large

capital investments. If location decision is wrongly made, the company’s performance

and profitability will be adversely affected. The objective of selecting the best location

for the plant is for maximum operating efficiency and effectiveness by minimizing

operating cost and achieving maximum revenues. Generally for plant selection,

following factors are considered:

Costs such as labor wages, utilities and transportation charges.

Government incentive offered to local entrepreneurs and foreign investors such

as tax concession and cheaper labor and land.

Safety of plant, personal, environment and community.

After the location of the site has been identify, we must come out with a proper

plant location to give the most economical flow of material and personnel around the

site. Several sites in Peninsular Malaysia have been taken into consideration. The site



1-28

that was considered is Gebeng (Pahang), Pasir Gudang (Johor), and Teluk Kalong

(Terengganu). Government assistance during the construction phase and possibility

also in the form of tariffs is possible depend upon which site will be located. The raw

material supply location should be nearer in order to save the transportation cost.

1.3.1.1. Marketing Area

For materials that are produced in bulk quantities, such as cement, mineral acids, and

fertilizers where the cost of the product per metric ton is relatively low and the cost of

transport is a significant fraction of the sales price, therefore, the plant should be

located to the primary market.

1.3.1.2. Raw Materials

The availability and price of suitable raw materials will often determine the site location.

Plants that produce bulk chemicals are best located close the source of major raw

material, as long as the costs of shipping product are not greater than the cost of

shipping feed.

1.3.1.3. Transportation

A site should be selected which is closed to at least two major forms of transport such

as road, rail, waterway or a sea port. Road transport is increasingly used and is suitable

for local distribution from a central warehouse. Rail transport is usually cheaper for

long-distance transport of bulk-chemicals.

1.3.1.4. Availability of Labor

Labor will be need for construction of the plant and its operation. Skilled craft workers

such as electricians, welders, and pipe fitters will be needed for plant maintenance.

Manpower is needed in order to control the process where the manual process and

required full attention to it.



1-30

After the location of the site, we must come out with a proper plant location to

give the most economical flow of material and personnel around the site. Several sites

in Peninsular Malaysia have been taken into considerations. The site that was

considered is Gebeng (Pahang), Pasir Gudang (Johor), and Teluk Kalong

(Terengganu). Government assistance during the construction phase and possibility

also in the form of tariffs is possible depend upon which site will be located. The raw

material supply is near and save the transportation cost.



1-32

Perindustrian Lpj 81700

Pasir Gudang, Johor

Lebuhraya Pantai Timur

and Lebuh raya Pasir

Gudang

60 km to BASF

PETRONAS, Kuantan

through T8 and Jalan

Jabor-Al Muktafi Billah

Shah

Perindustrian Gebeng ,

26080, Kuantan Pahang

iii. Para-toluene

sulphuric acid

691 km to KZH Chemicals

Sdn. Bhd., Bukit Mertajam

Penang through

Lebuhraya Utara-Selatan

628 km to KZH Chemicals

Sdn. Bhd. through

Lebuhraya Pantai timur

and Lebuhraya Utara-

Selatan

594 km to KZH ChemicalsSdn. Bhd. Through


and Lebuh raya Utara-

Selatan

iv. NaOH

CCM Chemicals Sdn Bhd

Plo 411, Jalan Perak

Satu, Kawasan 4,

Kawasan Perindustrian

Pasir Gudang, 81700

Johor Baru, Johor.

370 km to Mey Chern

Chemicals Sdn. Bhd.No.25, Jalan Selat Selatan

23, Sobenajaya Light

Industrial Estate

Pandamaran 42000 Port

Klang, Selangor

345 km to Mey Chern

Chemicals Sdn. Bhd. Port

Klang, Selangor through


440 km to CCMChemicals Sdn Bhd, Pasir

Gudang, Johor

296 km to Mey Chern

Chemicals Sdn. Bhd. Port

Klang, Selangor through


406 km to CCMChemicals Sdn Bhd, Pasir

Gudang, Johor

3. Transpo rt faci l i t ies Next to Johor Port (with

a 1000 metre berth of

cargo jetty, 3 hazardous

Kemaman Port(It is the

deepest port

in Malaysia and is an

important LNG shipment

Kuantan Port

(Centralized tankage

facilities, container and

bulk liquid port, pipeline

http://en.wikipedia.org/wiki/Malaysia

http://en.wikipedia.org/wiki/LNG

http://en.wikipedia.org/wiki/LNG

http://en.wikipedia.org/wiki/Malaysia



1-33

liquid bulk terminals)

Tanjong Pelepas Port, a

world class container port

Tanjung Langsat Port

(located adjacent to the

4000 acres of a industrialland in Tanjung Langsat,

equipped with a twin-berth

jetty consisting of outer

(30 000 DWT) and inner (

7000 DWT) berth

Road:

- Pasir Gudang

Highway

- Trunk road

- Railway line

Airport:

Senai International

Airport(40km)

port.)

Kuantan Port in

Pahang(Centralized

tankage facilities,

container and bulk liquid

port, pipeline and piperack

system connecting

Gebeng to Kuantan Port,railway linking Kertih,

Gebeng and Kuantan

Port)

Industrial Area is serviced

by Kuantan-Kerteh Rail

Link

Airport

- Kuantan Airport

- Kemaman Port

Airport

- Kuala Terengganu

Airport

and piperack system

connecting Gebeng to

Kuantan Port, railway

linking Kertih, Gebeng

and Kuantan Port)

Kuantan-Kerteh Rail Link

East Coast Highway

Kuantan-Kemaman

Coastal Road Kuantan Bypass

Airport:

- Kuantan Airport

- Kemaman Port Airport

4. Avai labi l i ty of labor

(rate of unem ployment, %) Available Available Available

5. Avai labi l i ty of ut i l i t ies

Water : Syarikat Air Johor

Electricity: Tenaga

Nasional Berhad

Water : SATU(Syarikat Air

Terengganu)

Electricity: Tenaga

Nasional Berhad

Water : Jabatan Bekalan

Air Pahang

Electricity: Tenaga

National Berhad



1-34

Price rate for electricity

Electricity Rates

Effective 1st March 2009, the electricity rate for Peninsular Malaysia has been revised as

follow: Industrial Tariffs - for factories

Tariff E3

High Voltage Peak/On-Peak Industrial Tariff RM/kW 0.2810

Price rate of water0-20m3 : RM2.22

More than 20m

3

: RM2.96

0-35m3 : RM2.07

More than 35m

3

: RM2.28

0-227m3 : RM0.92

More than 227m

3

: RM0.84

6. Avai labi l i ty of suitable

land

Available

Land: 58.8 acres

Available

Land: 125.1Hectares

Available

Land: 50 acres

7. Envi ronmental impact

and ef f luent disposal

Environment

Technology Park

(incorporating a training

centre, a waste collection

and processing centre as

well as raw materialmanagement and storage

facilities, maintenance

and servicing facilities)

Environment

Technology Park




well as raw materialmanagement and storage



Environment

Technology Park




well as raw material

management and storage



Urban Environmental

Industries Sdn Bhd and

NFP Industries Sdn Bhd

which handle scheduled

wastes. TCL Industries

(M) Sdn Bhd that located

in Teluk Kalung Industrial

Estate-60km.



1-35

8. Local comm uni ty

considerat ion

Basic needs for labors

near to town

schools for

youngsters

banks

shop lots


near to town

schools for

youngsters

banks

shop lots


near to town

schools for

youngsters

banks

shop lots

9. Climate

Johore's climate is tropical

monsoon. The temperature is

relatively uniform within the

range of 26°C to 27°C

throughout the year. During

the months of January to

April, the weather is

generally dry and warm.

Humidity is consistently high

on the lowlands ranging

between 82% to 86% per

annum. The average rainfall

per year is 2,030 mm to

3,050 mm and the wettest

months are from May to

December.

Selangor’s climate is a

tropical monsoon climate.

Selangor's climate is typified

by warm (sometimes hot)

and sunny days, and cool

evenings. Temperatures

typically range from 23°C to

33°C.

Humidity levels are generally

80 per cent or higher and

annual rainfall often exceeds

2,600mm. Although some

rainfall can be expected

throughout the year, the

period from December to

February is considered the

rainy season.

When the rainy season ends,

days are normally warm to

Pahang's climate is tropical

monsoon. The temperature is

relatively uniform within the

range of 21°C to 32°C

throughout the year. During

the months of January to

April, the weather is

generally dry and warm.

Humidity is in the range of

80%. The average rainfall

per year is 2,000 mm to

2,500 mm and the wettest

months are from May to

December.



1-36

hot, and dry (humidity levels

remain high). This period

runs from late January

through April. From March to

October, both rainfall and

humidity are at their lowest

levels and temperatures arepleasant.

10. Pol i t ical and strategic

considerat ions

Stable Stable Stable



1-37

Marks were given for evaluating the most suitable location. Marks in range 1-10 which

mean 10 is the best indication for the factors that will being considered where else 1

represent bad.

Table 1.11 Factors being considered according to the location

Factors being

considered

Proposed

Location

Gebeng , PahangTeluk Kalong,Terengganu

Tanjunglangsat, PasirGudang Johor

1. Location, withrespect to themarketing area

9 7 8

2. Raw material supply 8 6 7

3. Transport facilities 10 9 84. Availability of labor 9 9 9

5. Availability of utilities;water, fuel, power

8 7 7

6. Availability ofsuitable land

9 8 9

7. Environmentalimpact and effluentdisposal

7 7 8

8. Local communityconsideration

9 8 9

9. Climate 8 8 810. Political and strategic

consideration10 8 9

Total 87 77 82

From the available info and the weight comparison, it seems that Gebeng

Industrial Park is the best choice. For a budget of RM200 millions and minimum

production of 100,000 metric tonnes per year, we decided Gebeng Industrial Park in

Pahang is our site location for production of 2-Ethylhexyl Acrylate plant. This is because

Gebeng is fully the requirements of site selection considerations and most strategic

location based on the all criterias of site selection. The availability of labor also plays an

important role in choosing a plant location.



1-38

1.3.2. FACILITIES PROVIDED AT GEBENG INDUSTRIAL PARK

1.3.2.1. Training

In increasing demand for skilled workers, training facilities such as Industrial Training

Institute of Kuantan (ILP) has located a training centre within Gebeng to facilitate the

provision of highly skilled workforce to the requirement of industries. The training

schemes of ILP is recognised by the National Vocational Training Council and the

courses offered relates to the industries set up within Gebeng such as general

machining, welding, metal structural preparations and erection, sheet metal fabrication,

electrical wiring, industrial and consumer electronics as well as architectural

draughtsmanship. This ensures necessary labour skills are readily available for

operations at Gebeng whenever required.

1.3.2.2. Waste Management

The ETP(Environment Technology Park) Eco-complex is created as a concerted effort

to provide an efficient and effective waste management alternative for the handling and

disposal of industrial waste and byproducts generated by the different industries in

Kuantan and the Eastern Corridor. The ETP Eco-complex will provide land area and

facilities for the handling, storage, warehousing, pretreatment, disposal and recycling ofwaste materials generated by the existing chemical and petrochemical industries in the

Gebeng Industrial District and surrounding vicinities.

1.3.2.3. Government Agencies

The Pahang State Development Corporation (PSDC), a government agency entrusted

by the state government to develop Gebeng Industrial Area had established a site office

at the Gebeng Commercial Centre which is located within the Gebeng Industrial Area.The office's function is to enable delivery of continuing efforts in building Gebeng as a

leading chemical and petrochemical centre.

It also serves as point of reference to adress investors' needs arising from day-

to-day operations. Another government agency, SIRIM, the accreditation body in



1-39

Malaysia for certification of manufactured products for their quality in meeting

benchmarks and standards will be operating a centre within 5 kilometres from Gebeng

Industrial Area.

1.3.2.4. Safety of the Plant

In promoting for an incident and disaster-free environment for chemical and

petrochemical employees at all levels, the Kuantan Fire Department had established a

fire station within the Gebeng Industrial Area. In addition, a volunteer crisis

management organisation has been set up under the Gebeng Emergency Mutual Aid

('GEMA') offering expertise to counter emergencies in the vicinity of Gebeng and

Kuantan Port. GEMA is a joint effort between government agencies, Kuantan Port and

chemical and petrochemical manufacturers located at Gebeng Industrial Area andKuantan Port Industrial Area such as Amoco, BASF, Kaneka, Eastman Chemical,

Malaysian Oxygen, Exxon Oil, MTBE/Polypropylene Malaysia, Polyplastic Asia Pacific,

Shell, W.R. Grace Specialty Chemicals, Gas Malaysia and Flexsys Chemicals.

The following figures shows the availability of land in the Gebeng Industrial Park 2.

Figure 1.12 Gebeng Industrial Area

Source: PERBADANAN KEMAJUAN NEGERI Pahang (2010)



1-40

Therefore, from the information gained from MIDA, the vacant land is available at

Gebeng Industrial Park 2 with the price of RM 8/sq.ft.

Figure 1.13 Gebeng Industrial Park Area

Source: PERBADANAN KEMAJUAN NEGERI Pahang (AUG, 2010)

Figure 1.14 Available land at Gebeng Industrial Park 2 (starproperty.com)



1-41

Figure 1.15 The proposed land for industrial at Gebeng 2 (starproperty.com)

Figure 1.16 The proposed land for industrial at Gebeng 2 (starproperty.com)

CHAPTER 1 FEASIBILITY STUDY.pdf

Documents

Transcript of CHAPTER 1 FEASIBILITY STUDY.pdf