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Polystyrene (PS)
Acrylonitrile Butadiene Styrene (ABS)

Ethyl Benzene
Styrene

Benzene

Styrene- Acrylonitrile (SAN)


Styrene Butadiene Rubber (SBR)

Cyclohexane
Caprolactam

Polyamide(Nylon 6)

Adipic acid

Polyamide(Nylon 6,6)

Cumene

Phenolic resins

o-Xylene

Phenol

Phthalic Anhydride (PA)

Bisphenol A (BPA)

Polycarbonate (PC)

Alkyd Resin
Unsaturated Polyester Resin
Diisooctyl Phthalate (DOP)

Aromatics
Units

Purified Terephthalic Acid (PTA)

Polyester Polyol for Polyurethane


Poly(Ethylene Terepththalate) (PET)

p-Xylene

Poly(Butylene Terephthalate) (PBT)

Dimethyl Terephthalate (DMT)

Isophthalic Acid

Aromatic Polyamide

Diphenyl Isophthalate

m-Xylene
Toluene Diisocyanate (TDI)

TNT Trinitrotoluene

Toluene

Benzoic Acid

Polyurethane

BENZENE
Specifications
Production
Global
Production in
Thailand

1,277 (103 ton/year)

PTTAR

670

1. Catalytic reforming

TPX

177

2. Steam cracking

ROC

70

3. Toluene hydrodealkylation (HDA)

MOC

160

4. Toluene disproportionation (TDP)

IRPC

110

The under development process

Source: Petroleum Institute of Thailand (PTIT)s


Industry Survey Version 1/2010 as of February 2011

The major process for producing benzene

1. Pyrolysis of poly(butylene terephthalate)


and poly(ethylene naphthalene-2,6-dicarboxylate) in

the presence of calcium hydroxide


2. Dehydro-aromatization of methane from biogas

World market trend

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BENZENE SPECIFICATIONS
IUPAC name: Benzene
Systematic name: Cyclohexa-1, 3, 5-triene
Other names: 1,3, 5-cyclohexatriene, Benzol

Benzene molecular formula [homepage on the Internet]. [cited 2014 June 20].
Available from: http://en.wikipedia.org/wiki/BTX_(chemistry)

Thermochemistry
Specific heat capacity: 136.0 J/Kmol
Std molar entropy: 173.26 J/Kmol
Std enthalpy of formation: 48.7 kJ/mol

Properties
Molecular formula: C6H6
Molar mass: 78.11 g/mol
Appearance: Colorless liquid
Odor: Aromatics, gasoline-like
Density: 0.8765 (20) g/cm3
Melting point: 278.85 K
Boling point: 353.45 K
Solubility in water: 0.00179 g/cm3 ( 288.15 K)
Solubility: Soluble in alcohol, chloroform, CCl4, diethyl ether, acetone
Vapor pressure: 10 kPa

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BENZENE PRODUCTION
1. Catalytic Reforming

cyclohexane
Methyl
cyclopentane

Catalytic reforming [homepage on the Internet]. [cited 2014 June 20].


Available from: http://en.wikipedia.org/wiki/BTX_(chemistry)

benzene

n-hexane

benzene

Process
Catalysts: Silica or alumina coated with platinum, palladium, or rhodium
Temperature: 699.82 783.15 K
Pressure: 1,379 5,516 kPa
Reaction time: 30 minutes

Note
- An important by-product of reforming operations is hydrogen, which is react with carbon
depositing on the catalyst to form methane.
- The reformate stream, which is high in octane, makes an excellent gasoline blending
component.
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BENZENE PRODUCTION
2. Steam Cracking

n-hexane

Steam Cracking [homepage on the Internet]. [cited 2014 June 20].


Available from: http://www.2b1stconsulting.com/propylene/

n-hexene

benzene

Process
- Steam cracking is the process for producing ethylene and other alkenes from aliphatic
hydrocarbons. Depending on the feedstock used to produce the olefins, steam cracking can produce
a benzene-rich liquid by-product called pyrolysis gasoline. Pyrolysis gasoline can be blended with
other hydrocarbons as a gasoline additive, or routed through an extraction process to recover BTX
aromatics (benzene, toluene and xylenes)
Temperature: > 1199.82 K
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BENZENE PRODUCTION
3. Toluene Hydrodealkylation (HDA)

Toluene

benzene

Toluene Hydrodealkylation [homepage on the Internet]. [cited 2014 June 20].


Available from: http://nptel.ac.in/courses/103103029/module3/lec21/3.html

Process
-

Toluene is mixed with hydrogen, heated, and pumped in to a reactor.


The reactor is packed with platinum catalyst and run at high pressures and
temperature.
The methyl group pops off as the toluene passes over the catalyst and is replaced by
a hydrogen atom and forming benzene.

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BENZENE PRODUCTION
4. Toluene Disproportination (TDP)

Toluene benzene

Toluene Disproportionation [homepage on the Internet]. [cited 2014 June 20].


Available from: http://www.exxonmobilchemical.com

Process
-

The toluene disproportionation process, a methyl group leaps off one toluene molecule
(and it replaced by hydrogen) and attaches itself to another toluene molecule (replacing
by hydrogen atom). That leaves one benzene molecule and one xylene molecule.
Effective catalysts include some of the noble metals, specifically Pt and Pd deposited on
alumina pelllets.
The reactor is operated at temperatures from 923.15 K to 1223.15 K and pressure ranging
from 1034.25 kPa to 3447.5 kPa.
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BENZENE PRODUCTION
1. Pyrolysis of Polybutylene Terephthalate (PBT)
in the Presence of Calcium Hydroxide

Comparison of the GC-MS spectra of the


pyrolysis of PBT in the presence of Ca(OH)2.

The highest yield of benzene (67%) was obtained at a


Reaction scheme of the thermal degradation of temperature of 973.15 K and a molar Ca(OH)2/PBT ratio
PBT in the presence of Ca(OH)2 at 973.15 K.
of 10.
Toshiaki Yoshioka , Guido Grause , Shoichi Otani , Akitsugu Okuwaki , Selective production of benzene and naphthalene from
poly(butylene terephthalate) and poly(ethylene naphthalene-2,6-dicarboxylate) by pyrolysis in the presence of calcium hydroxide ,
Polymer Degradation and Stability 91 (2006) 1002-1009.

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BENZENE PRODUCTION
2. Dehydro-aromatization of Methane from Biogas

Flow diagram of the demonstration plant for co-production of hydrogen and benzene from biogas

This study tested the feasibility of the system for co-production of hydrogen and benzene from
biogas can co-produce 134 Nm3/day of hydrogen and 8.6 L/day of benzene from 200 Nm3/day
of biogas.
Yukoh Shudoa, Takashi Ohkubo, Yoshiaki Hideshima, Tomohiro Akiyama, Exergy analysis of the demonstration plant for co-production of
hydrogen and benzene from biogas, international journal o f hydrogen energy 34 (2009)4500-4508.

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BENZENE WORLD MARKET TREND

Global benzene consumption [homepage on the Internet]. [cited 2014 June 26].
Available from: http://mcgroup.co.uk/researches/bisphenol-a-bpa

Production of ethylbenzene and cumene now accounts for almost 4/5 of world benzene
demand. Because of its by-product status it is demand for gasoline, ethylene and
paraxylene that determines situation in benzene industry. Gasoline, ethylene and
paraxylene are forecast to grow thus benzene is seen to be in high supply in the future.

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BENZENE WORLD MARKET TREND

Benzene world market trend [homepage on the Internet]. [cited 2014 Aug 10]. Available from: http://www.icis.com/blogs/chemicalsand-the-economy/2013/11/benzene-markets-suggest-babyboomer-growth-will-reappear/

Benzene has always been one of the indicators for the global economy. The reason is simple, in
that it has been around a long time, and is now used in a very wide range of industries. The chart
above highlights another important factor, that we have a continuous history of its production
going back to 1960.
- 1950-75 saw average growth of 9%/year, as markets developed rapidly under the influence of
low prices and increasing availability.
- Demand increased again as the arrival of the BabyBoomers in their peak consumption years
led to the growth SuperCycle between 1983-2007.
- Annual volume rose 4%/year from 15MT/year to 41MT/year over the period.
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ETHYLBENZENE (EB)

Specifications
Production
The major process for producing ethyl benzene
1. Friedel-Crafts Reaction (Liquid phase operation)
2. Friedel-Crafts Reaction (Vapor phase operation)
3. Alternate Ethyl Benzene Technology

World market applications

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ETHYLBENZENE SPECIFICATIONS

2014

IUPAC name: Ethylbenzene


Other names: Ethylbenzol, phenylethane,
alpha-methyltoluene
Thermochemistry
Specific heat capacity: 1.726 J/g.K

Properties
Molecular formula: C6H5CH2CH3
Molar mass: 106.17 g/mol
Appearance: Colorless liquid
Odor: Aromatics, gasoline-like
Density: 0.8665 g/cm3
Melting point: 178.15 K
Boling point: 409 K
Solubility in water: 0.015 g/100 cm3 (293 K)
Vapor pressure: 1.3 kPa

Hazards
Main hazard: Flammable
Flash point: 295.37 K
Explosive limit: 1% 7.8%
LD50: 5460 mg/kg

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ETHYLBENZENE PRODUCTION
1. Friedel-Crafts Reaction (Liquid phase operation)

Benzene

Ethylene

Ethylbenzene

Processes
Catalysts: Anhydrous aluminum chloride
Temperature: 422.04 477.6 K
Pressure: 413.7 689.5 kPa
Reaction time: 30 minutes
Promoter/Accelerator: Ethyl chloride

Note
- Caustic (sodium hydroxide) and water are used to remove the catalyst.
- The presence of any water in the reactor would cause lots of undesirable side reactions.

Donald L. Burdick, William L, Leffler, Petrochemicals in nontechnical language fourth edition, PennWell corporation, 2010, p. 103-107

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ETHYLBENZENE PRODUCTION
2. Friedel-Crafts Reaction (Vapor phase operation)

Benzene

Ethylene

Ethylbenzene

Process
Catalysts: Boron trifluoride, crystalline aluminosilicate zeolite (noncorrosive and nonhazardous)
Temperature: 672.04 699.82 K
Pressure: 3102.75 kPa

Note
-The vapor process utilized a dual reactor because the catalyst must be regenerated every 8 weeks.

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Donald L. Burdick, William L, Leffler, Petrochemicals in nontechnical language fourth edition, PennWell corporation, 2010.

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ETHYLBENZENE PRODUCTION
3. Alternate Ethyl Benzene Technology

Processes
This process is catalytic dehydrogenation of ethane to ethylene, followed by its reaction with
benzene to produce ethyl benzene.
Catalyst step 1: A gallium zinc zeolite
Catalyst step 2: A silica mordenite
Temperature: 616.49 644.26 K
Pressure: Atmospheric pressure

Note
- Available for those remote places where olefin plants are not nearby but supply with ethane.
Donald L. Burdick, William L, Leffler, Petrochemicals in nontechnical language fourth edition, PennWell corporation, 2010, p. 103-107

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ETHYLBENZENE WORLD MARKET APPLICATIONS

Global ethyl benzene consumption [homepage on the Internet]. [cited 2014 June 26].
Available from: http://mcgroup.co.uk/researches/ethylbenzene-eb

Ethylbenzene (EB) market is closely linked to styrene demand. It is the largest


ethylbenzene application, accounting for 99% of global product demand; 1% of global
EB output is used as an intermediate in chemical production.

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STYRENE

Global
Production in
Thailand

520 (103 ton/year)

SSMC

320

IRPC

200

Source: Petroleum Institute of Thailand (PTIT)s


Industry Survey Version 1/2010 as of February 2011

Specifications

Production
The major processes for producing ethylbenzene
1. Ethyl benzene dehydrogenation

2. Peroxide (PO)/Styrene process (Alternative route to styrene)

World market applications

Donald L. Burdick, William L, Leffler, Petrochemicals in nontechnical language fourth edition, PennWell corporation, 2010, p. 108-116

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STYRENE SPECIFICATIONS
IUPAC name: Phenylethene
Other names: Vinyl benzene, styrol,
phenylethene, phenylethylene, styrolene

Properties
Molecular formula: C8H8
Molar mass: 104.15 g/mol
Appearance: Colorless oily liquid
Odor: Sweetish, aromatic
Color: Colorless
Density: 0.909 g/cm3
Melting point: 243.15 K
Boling point: 418.15 K
Solubility in water: <1%
Vapor pressure: 0.592 kPa

Hazards
Main hazard: Flamable, toxic
Flash point: 304.25 K
Auto-ignition temperature: 763.15 K
Flammable limit: Lower 1.1%, Upper 6.1%
Product of combustion: CO, CO2

Donald L. Burdick, William L, Leffler, Petrochemicals in nontechnical language fourth edition, PennWell corporation, 2010, p. 108-116

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STYRENE PRODUCTION
1. Ethylbenzene dehydrogenation

Process
The dehydrogenation step is endothermic reaction. Superheated steam, mixed with EB
could reduces the operation pressure and coke formation.

Catalyst: Iron oxide


Temperature: 894.27 K

Note
- Even at ambient temperature, styrene trends to react with itself. A small amount of paratertiarybutyl catechol (polymerization inhibitor) is added to styrene and kept in storage.
Donald L. Burdick, William L, Leffler, Petrochemicals in nontechnical language fourth edition, PennWell corporation, 2010, p. 108-116

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STYRENE PRODUCTION
2.Peroxide (PO)/Styrene process (Alternative route for styrene)
Process

eEthylbenzene

Step 1: EB is oxidized to a hydroperoxide


Temperature: 433.15 K
Pressure: 3447.5 kPa

Hydroperoxide

Step 2: The EB hydroperoxide react with


propylene to produce propylene oxide and
methylbenzyl alcohol.
Temperature: 394.26 K
Pressure: 1723.75 4826.5 kPa
Hydroperoxide

Propylene

Methylbenzyl alcohol

Methylbenzyl alcohol

Propylene oxide

Step 3: The methylbenzyl alcohol is dehydrated


in the vapor stage to form styrene.
Temperature: 505.37 533.15 K
Pressure: 3447.5 kPa
Catalyst: Titanium dioxide or silica gel

Mono styrene

Note
- Hydroperoxide is very unstable compounds so its exposure to high temperature has to be limited.
- The overall yield of styrene via this peroxidation process route is 90%.
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Donald L. Burdick, William L, Leffler, Petrochemicals in nontechnical language fourth edition, PennWell corporation, 2010, p. 108-116

STYRENE WORLD MARKET APPICATIONS

Global styrene consumption [homepage on the Internet]. [cited 2014 June 20].
Available from: http://mcgroup.co.uk/researches/styrene

Global styrene consumption is driven by polystyrene and expanded polystyrene (EPS)


demand (other minor applications include styrene butadiene (SB) latex, unsaturated
polyester resin, styrene-butadiene rubber (SBR), etc.

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POLYSTYRENE

Specifications
Production
Applications

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POLYSTYRENE SPECIFICATIONS
IUPAC name: Poly(1-phenylethylene)
Other names: Thermocole
Mechanical Properties

Properties
Molecular formula: (C8H8) n
Appearance: Colorless , clear
Color: Colorless
Density: 0.96 - 1.04 g/cm3
Melting point: 513.15 K
Specific gravity: 1.03 1.06 g/cm3
Apparent density: 0.60 0.65 g/cm3
Thermal conductivity: 0.033 W/m.K
Glass transition temperature : 373.15 K
Water absorption: 0.03 - 0.1%

Tensile modulus: 3000 3600 MPa


Tensile strength: 30 60 MPa
Tensile elongation: 1 5%
Shear modulus: 1400 MPa
Flexural strength: 76 MPa
Flexural modulus: 3200 MPa

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POLYSTYRENE PRODUCTION
Process
Step 1 Begin in a prepolymerizer, the styrene is partially polymerized (about 30 %).
Reactor: A water- jacketed reactor with in-situ mixer
Initiator: Peroxide initiator
Temperature: 388.71 394.26 K
Time: 4 hours
Step 2 Continue in tower reactor
Reactor: Vertical jacketed tower with internal temperature-regulating coils
Temperature: 410.93 K (at the top) and 477.6 K (at the bottom)
Time: 3 4 hours

Note
- Bulk, liquid, slurry, and gas phase polymerization processes can be used to make polystyrene (PS).
- The reaction temperatures are controlled to prevent runaway but still allow 95% conversion of
styrene to PS.
- The most critical factor is the temperature in the 2nd reactor. If hot spots develop, a runaway can
occur.

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Donald L. Burdick, William L, Leffler, Petrochemicals in nontechnical language fourth edition, PennWell corporation, 2010.

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POLYSTYRENE APPLICATIONS
Application
Polystyrene is a "polymer of styrene. it has a good impact resistance, lightweight and rigid
transparent thermoplastic .
Various Applications of Polystyrene
Packaging
Construction

Appliances

Medicals

Consumer electronics
Others (About 25% of polymerized styrene is
used in the copolymer.)

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ACRYLONITRILE BUTADIENE STYRENE

Specifications
Production
Applications

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ACRYLONITRILE BUTADIENE STYRENE SPECIFICATIONS


Mechanical Properties
Tensile modulus: 2,460 4,100 MPa
Tensile strength: 49.4 74.2 MPa
Tensile elongation: 2 12 %
Shear modulus: 1,400 MPa
Flexural strength: 75.4 118.0 MPa
Flexural modulus: 2230 4170 Mpa

Properties
Molecular formula: (C8H8)x (C4H6)y(C3H3N)z
Appearance: Gloss , haze, transmittance
Apparent density: 0.25 0.36 g/cm3
Glass transition temperature : 377.6 K
Glow wire flammability index: 916.49 1,233.16 K
Glow wire ignition temperature: 822.04 1,233.16 K

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ACRYLONITRILE BUTADIENE STYRENE PRODUCTION

ABS production [homepage on the Internet]. [cited 2014 June 20].


Available from: http://www.toyo-eng.co.jp/en/advantage/technology/petrochemistry/styrene/

Process
Styrene and acrylonitrile are mixed in a bulk liquid form and introduce to a prepolymerizer
with dissolved rubber (polybutadiene). The rubber phase is dispersed by grafting particulate
in a thermoplastic matrix of styrene and acrylonitrile copolymer (SAN) reform ABS.

Note
A chemical connection between elastomer molecules and the styrene acrylonitrile
copolymer is created by polymerizing styrene and acrylonitrile in the presence of
polymerized elastomer.
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ACRYLONITRILE BUTADIENE STYRENE APPLICATIONS


Applications
Acrylonitrile butadiene styrene (ABS) is one of the few plastics that combines both toughness and
hardness. It is a copolymer of the three monomers and creating a plastic that comes in a variety of
grades. The proportions can vary from 15 to 35% acrylonitrile, 5 to 30% butadiene and 40 to 60%
styrene.
ABS can be found in:
- Domestic appliance and telephone housings
- Luggage
- Sport helmets
- Linings for refrigerator doors
- Computer cases
- Manufacture of sanitary piping (as a substitute for PVC)
- Automotive industry, because of its ability to be covered in chrome
- Alloys with other plastics, e.g., ABS with PVC plastic gives a high resistance to flame and is there
used in the manufacture of television sets.

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STYRENE ACRYLONITRILE (SAN)

Specifications
Production
Applications

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STYRENE ACRYLONITRILE SPECIFICATIONS


Mechanical Properties
Tensile modulus: 4,500 5,380 MPa
Tensile strength: 92.30 117.00 MPa
Tensile elongation: 2.5 4.1 %
Flexural strength: 126 174 MPa
Flexural modulus: 4,410 5,500 MPa
Flexural at yield: 128 179 MPa
Properties
Molecular formula: (C8H8)n-(C3H3N)m
Appearance: Haze, transmittance
Apparent density: 0.65 0.69 g/cm3
Water absorption: 0.29 0.30 %
Glass transition temperature: 373.15 K

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STYRENE ACRYLONITRILE PRODUCTION

SAN production [homepage on the Internet]. [cited 2014 June 20].


Available from: http://www.toyo-eng.co.jp/en/advantage/technology/petrochemistry/styrene/

Process
The two compounds (styrene units and acrylonitrile units) are mixed in bulk-liquid form or in a
water-based emulsion or suspension, and polymerization is conducted under the action of freeradical initiators.

Note
Styrene acrylonitrile copolymer (SAN) consists of styrene units and acrylonitrile units in a ratio
of approximately 70 to 30.
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STYRENE ACRYLONITRILE APPLICATIONS


Applications
Styrene acrylonitrile copolymer (SAN), a rigid and transparent plastic that is produced by the
copolymerization of styrene and acrylonitrile. SAN combines the clarity and rigidity of
polystyrene with the hardness, strength, and heat and solvent resistance of poly acrylonitrile.
SAN Common Uses:
Industrial uses: Battery cases, dials, knobs, switches, lenses
Consumer Products: Cups, , trays, containers, covers, cassette cases, , mixers, juicers, pencil
cases, stereo dust covers, hangers, cosmetic containers
Medical Applications: Autoclavable devices, dental & medical light diffusers
Electrical/Electronic: Battery housings, telephone components, radios, CD-players, meter covers

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STYRENE BUTADIENE RUBBER (SBR)

Specifications
Production
Applications

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STYRENE BUTADIENE RUBBER SPECIFICATIONS


Mechanical Properties
Bulk modulus: 1,500 2,000 MPa
Youngs modulus: 2 10 MPa
Shear modulus: 0.7 3 MPa
Tensile strength: 12 21 MPa
Compressive strength: 14.4 25.2 MPa
Elastic limit: 12 21 MPa
Properties
Molecular formula: (CH2-C(CH3)-C(CH3)-CH2)n
Atomic volume: 0.0055 0.0065 g/cm3
Apparent density: 0.94 0.95 g/cm3
Specific heat : 2000 2200 J/kg K
Glass transition temperature: 210 215 K
Thermal conductivity: 0.143 1.48 W/ m K
Thermal Expansion: 660 675 10-6/K

SBR specification [homepage on the Internet]. 2014 [cited 20014 June 20]. Available from: http://www.azom.com/properties.aspx?ArticleID=1844 /

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STYRENE BUTADIENE RUBBER PRODUCTION


Emulsion polymerization
Reaction vessels are typically charged with the
two monomers, a free radical generator, and a
chain transfer agent such as an alkyl mercaptan.
Radical initiators include potassium persulfate
and hydroperoxides in combination with ferrous
salts.

SBR production [homepage on the Internet]. [cited 2014 July 16].


Available from: http://www.britannica.com/EBchecked/topic/570377/styrene-butadiene-rubber-SBR

Solution polymerization
Solution-SBR is produced by an anionic polymerization process. Polymerization is initiated
by alkyl lithium compounds. The process is homogeneous (all components are dissolved), which
provides greater control over the process, allowing tailoring of the polymer. The organolithium
compound adds to one of the monomers , generating a carbanion that then adds to another
monomer, and so on.
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STYRENE BUTADIENE RUBBER APPLICATIONS


Styrene-butadiene rubber (SBR) describes families of synthetic rubbers derived
from styrene and butadiene. These materials have good abrasion resistance and good
aging stability when protected by additives. The elastomer is used widely in
pneumatic tires, shoe heels and soles, gaskets and even chewing gum. It is a commodity
material which competes with natural rubber.

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CYCLOHEXANE

Global
Production in
Thailand

200 (103 ton/year)

PTT AR

200

Source: Petroleum Institute of Thailand (PTIT)s


Industry Survey Version 1/2010 as of February 2011

Specifications
Production
The major process for producing cyclohexane
1. The traditional process
2. The liquid phase process

World market applications

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CYCLOHEXANE SPECIFICATIONS
Thermochemistry
Std enthalpy of formation: -156 kJ/mol
Std enthalpy of combustion: -3920 J/mol

Hazards
Properties
Molecular formula: C6H12
Molar mass: 84.16 g/mol
Appearance: Colorless liquid
Odor: Distinctive detergent-like
Density: 0.7781 g/cm3
Melting point: 279.62 K
Boling point: 353.89 K
Solubility in water: Immiscible
Vapor pressure: 22.21 kPa

Main hazard: Flamable


Flash point: 243.15 K
Harmful: Severe eye irritant, may cause corneal
clouding

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CYCLOHEXANE PRODUCTION

1. The traditional process

Process
Catalysts: Charcoal or alumina coated with metals (Pt, Pd, Ni, or Cr)
Temperature: 477.6 K
Pressure: 2,758 kPa
Reactor: Vessels filled with catalyst. The catalyst is packed loosely enough that the feed can flow
through by gravity.
Conversion: Typically 99.5%

Note
- Sulfur and carbon monoxide can deactivate the hydrogenation catalysts. (The sulfur resistant catalyst
metal: Ti, Mo)
- Pt and Pd are highly active and can cause hydrogenation at room temperature. Due to the metal
price, most commercial processes use Ni or Cr even they require higher temperature and pressure.
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Donald L. Burdick, William L, Leffler, Petrochemicals in nontechnical language fourth edition, PennWell corporation, 2010.

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CYCLOHEXANE PRODUCTION
2. The liquid phase process

Processes
Catalysts: Raney nickel catalyst
Temperature: 449.82 477.6 K
Pressure: 2,758 kPa
Reactor: 1. Main reactor (catalysts slurry) 2. Finishing reactor (fixed bed reactor)
Conversion: 100% conversion with purity about 99%

Note
- The efficiencies come from running a liquid phase system, saving heat and catalyst handling
equipment.
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Donald L. Burdick, William L, Leffler, Petrochemicals in nontechnical language fourth edition, PennWell corporation, 2010,

CYCLOHEXANE WORLD MARKET APPLICATION

Global cyclohexane consumption [homepage on the Internet]. [cited 2014 July 16].
Available from: http://mcgroup.co.uk/researches/bisphenol-a-bpa

Cyclohexane (or CX) is mainly used for production of cyclohexanol and cyclohexanone, which are
consumed in adipic acid and caprolactam manufacturing process. It also finds application as a solvent.
Today major CX consuming regions include Asia Pacific, EU countries and USA. Caprolactam demand
in Asia Pacific forces China to add new cyclohexane capacities. On the other hand, growth in other
markets, such as Europe and North America, is expected to slow down. However, in the near future
global cyclohexane market, which is strongly connected to automobile, construction and textile
industries, is expected to grow at nearly 3% per year.
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CAPROLACTAM

Specifications
Global
Production in
Thailand

130 (103 ton/year)

Ube Chemical

130

Source: Petroleum Institute of Thailand (PTIT)s


Industry Survey Version 1/2010 as of February 2011

Production
The major processes for producing caprolactam
1. Original process
2. Allied chemical phenol process
3. Cyclohexane process via cyclohexanone

World market applications

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CAPROLACTAM SPECIFICATIONS
IUPAC name: Azepan-2-one
Other names: 1- Aza-2-cycloheptanone,
2- azacycloheptanone, capron PK4

Hazards

Flash point: 398 K


LD50: 1.1g/kg, Mildly toxic not
carcinogenic to humans.

Properties
Molecular formula: C6H11 NO
Molar mass: 113.16 g/mol
Appearance: White solid
Density: 1.01 g/cm3
Melting point: 342.3 K
Boling point: 544 K
Solubility in water: 4560 g/L (293 K)

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CAPROLACTAM PRODUCTION
1. Original Process:

2. Allied Chemical Phenol Process:

Both processes (original and allied chemical phenol) are originally produced caprolactam from
phenol, which is an intermediate chemical mainly used for bisphenol-A (BPA) and phenolic resins
production. Due to the increasing of BPA demand, nowadays carprolactam mainly produced from
cyclohexane.
Vaidya, A.A., Gupta D.C., Raw materials for synthetic fibers, Chemical Engineering World, Volume 21, No. 3, 1986, p. 35.

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CAPROLACTAM PRODUCTION

3. Cyclohexane Process, Via Cyclohexanone:


Step1

Cyclohexanone

Cyclohexane

Hydrogen

Separator

Cyclohexanol
hydrogenation

Cyclohexane
oxidation

Separator

Hydrogen

Cyclohexanol

Cyclohexanol and cyclohexanone

Step2
Cyclohexanone

Hydroxyl amine
sulphate
Oleum, 20%

Settler
Neutralization

Filtration

Ammonia

Backmann
rearangement

Cyclohexanone
oxidation

Ammonia and water

Neutralization

Caprolactam

Taverna, M., Chiti M., Routes to caprolactam, Hydrocarbon processing, November, 1970,p. 140.

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CAPROLACTAM PRODUCTION

3. Cyclohexane Process, Via Cyclohexanone:

Process
The two step processes of caprolactam production involves oxidation of cyclohexane (433.15 K)
to cyclohexanone followed by reacting cyclohexanone with hydroxylamine sulphate (433.15 473.15 K) in a multi compartment reactor.
Note
During this process ammonium sulphate is formed as byproduct. Caprolactam & aqueous
ammonium sulphate are sent to a series of extractors where toluene is used as a solvent..

Taverna, M., Chiti M., Routes to caprolactam, Hydrocarbon processing, November, 1970,p. 140.

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CAPROLACTAM WORLD MARKET APPLICATIONS

Global caprolactam consumption [homepage on the Internet]. [cited 2014 July 16].
Available from: http://mcgroup.co.uk/researches/caprolactam-cpl

Caprolactam (CPL) is mainly used in production of Nylon 6, which is then applied in manufacture
of textile yarn, industrial yarn, engineering plastics and carpet/staple fiber.
European region used to be a leader in caprolactam production, but in 2011 the shares of
European and Asian regions became almost equal. Today Asian region holds major share in global
caprolactam output due to commissioning of a new and expansion of existing facilities in China
and Thailand. In the future, Asia Pacific region is expected to reduce caprolactam imports and to
become self-sufficient.
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POLYAMIDE (NYLON 6)

Specifications
Production
Applications

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POLYAMIDE (NYLON 6) SPECIFICATIONS


IUPAC name: Poly(hexano-6-lactam)
Other names: Polycarprolactam,
PA6, cappron, nylatron, alphalon

Properties
Molecular formula: (C8H11 NO)n
Apparent density: 1.15 g/cm3
Water absorption: 0.3 % (24 h)
Melting Temp: 488.15 K
Auto ignition Temp: 707 K

Mechanical Properties
Tensile modulus: 2,758 MPa
Tensile strength: 83 MPa
Tensile elongation: 20 %
Flexural strength: 110 MPa
Flexural modulus:3,447 MPa
Compressive strength: 103 MPa
Compressive modulus: 2758 MPa
IZOD notched impact: 0.4 ft-lb/in

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POLYAMIDE (NYLON 6) PRODUCTION

Chavel, A., Lefebvre, G., Monomers for polyamide synthesis in Petrochemical


Processes-2, Editions Technip Paris, 1989, p. 233 & 287.

Process
Process steps involved in production of Nylon 6 include the following steps
- Caprolactam melting and addition of additives
- Polymerization: Batch/continuous and chips production
- Chips washing and drying
- Spinning of nylon
- Recovery section

Note
- Caprolactam is polymerized to Nylon 6 polymer by ring opening polymerization at 513 K
- 543.15 K in the presence of water.
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POLYAMIDE (NYLON 6) APPLICATIONS


Applications
Nylon 6 is a tough and abrasion-resistant material. It has improved surface appearance, creep
resistance, and processability compared to nylon 6/6. Nylon 6 finds application in a broad range
of products requiring materials of high strength. It is widely used for gears, fittings, and bearings,
in automotive industry for under-the-hood parts, and as a material for power tools housings.

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ADIPIC ACID

Specifications
Production
The major process for producing adipic acid
1. The two-step process by oxidized cyclohexane
(conventional method)

2. The new innovation method

World market applications


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ADIPIC ACID SPECFICATIONS


IUPAC name: Hexanedioic acid
Other names: Hexane-1,6-dioic acid

Thermochemistry
Std enthalpy of formation: -1021 KJ/mol
Properties
Molecular formula: C6H10 O4
Molar mass: 146.14 g/mol
Appearance: White crystals
Density: 1.360 g/cm3
Melting point: 425.4 K
Boling point: 610.6 K
Solubility in water: 2.4 g/100ml (298.15 K)
Solubility: Very soluble in methanol, ethanol
Vapor pressure: 0.0728 Pa (291.65 K)
Acidity: 4.43 5.41 pKa

Hazards
Flash point: 469 K
LD50: 3,600 mg/kg
Skin contact: Irritant
Eye contact: Irritant
Inhalation: Carcinogenic effect

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ADIPIC ACID PRODUCTION


1) The conventional method

Nitric acid

+ NOx

Ka Oil

Process
Step 1: Cyclohexane is oxidized with air to give a mixture of cyclohexanal and cyclohexanone (KA oil).
Catalyst: cobalt naphthenate

Step 2 : The two products are separated from the unreacted cyclohexanone and then hit with a 50%
nitric acid solution (nitric acid oxidation step).

Note
- An inevitable by-product of this reaction is nitrous oxide, implicated in the process of global warming
and ozone depletion.
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ADIPIC ACID PRODUCTION


2) The new innovation methods
1) Production of adipic acid using sodium tungstatecatalyzed oxidation of cyclohexene by hydrogen
peroxide in water.

2) A single-step air oxidation of cyclohexane,


based on a new lipophilic catalytic system,
leads to provide an environmentally benign
alternative to an important industrial reaction.

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ADIPIC ACID WORLD MARKET APPLICATIONS

Global adipic acid consumption [homepage on the Internet]. [cited 2014 July 21].
Available from: http://mcgroup.co.uk/researches/adipic acid.

Adipic acid is mainly used in production of Nylon 6-6, polyurethanes and adipic esters. Until recently,
the product has been manufactured from various petrochemicals, but today more ecological routes
to produce adipic acid are available. Verdezyne, BioAmber, Celexion and other companies today offer
bio-based adipic acid, which is more eco-friendly. But synthetic adipic acid still dominates the
market, which is forecast to grow at near 5% per year in future.

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POLYAMIDE (NYLON 6,6)

Specifications

Production
Applications

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POLYAMIDE (NYLON 6,6) SPECIFICATIONS


IUPAC name: Polyimmino(1,6-dioxohexamethylene)
Other names: Poly(hexamethylene adipamide),
poly(N,N-hexamethyleneadipinediamide),
marannyl

Properties
Molecular formula: (C12H22 N2O2)n
Apparent density: 1.14 g/cm3
Water absorption: 0.3 % (24 hr)
Melting Temp: 541.95 K

Mechanical Properties
Tensile modulus: 2930 MPa
Tensile strength: 79 MPa
Tensile elongation: 50 %
Flexural strength: 103 MPa
Flexural modulus: 3,103 MPa
Compressive strength: 86 MPa
Compressive modulus: 2,896 MPa
IZOD notched impact: 0.6 ft-lb/in

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POLYAMIDE (NYLON 6,6) PRODUCTION

Process
Process step involved in manufacture of Nylon 6,6
- Production of nylon salt (hexamethylene diammonium
adipate) by reaction of adipic acid
& hexamethylene diamine
- Polymerisation of nylon salt
- Cooling and chips production
- Spinning of nylon 6,6 chips
- Recovery section

Note
- Nylon salt (hexamethylene diammonium adipate) is
prepared by mixing adipic acid and hexamethylene diamine in
1:1 molar ratio.
Nair, S.R., Lal, I.B., Technology and applications of polyamides fibers, Seminar or synthetic chemical fibers in India in the coming decade,
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organised on IIChE North Regional Centre, New Delhi, 28 December, 1969, p. 17.

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POLYAMIDE (NYLON 6,6) APPLICATIONS


Applications
Nylon 6/6 is one of the most versatile engineering thermoplastics. It is popular in every major
market using thermoplastic materials. Because of its excellent balance of strength, ductility and
heat resistance, nylon 6/6 is an outstanding candidate for metal replacement application. Nylon
6-6 is frequently used when high mechanical strength, great rigidity, and good stability under
heat is required.

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CUMENE

Global
Production in
Thailand

270 (103 ton/year)

PTT Phenol

270

Source: Petroleum Institute of Thailand (PTIT)s


Industry Survey Version 1/2010 as of February 2011

Specifications

Production
The major process for producing Cumene
1. The phosphoric acid process

2. The catalytic distillation process using zeolite


3. Monsanto-Lmmus Crest cumene production process

World market applications


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CUMENE SPECIFICATIONS
IUPAC name: 1-Methyl)benzene
Systematic names: Prop-2-ylbenzene, 2-phenylpropene
Other names: i-Propylbenzene, isopropylbenzene

Hazards
Main hazards: flammable
Flash point: 425 K
Explosive limit: 0.9 6.5%

Properties
Molecular formula: C9H12
Molar mass: 120.19 g/mol
Appearance: colorless liquid
Density: 0.862 g/cm3
Melting point: 177 K
Boling point: 425 K
Solubility in water: negligible
Solubility: soluble in acetone, ether, ethanol

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CUMENE PRODUCTION
1) The phosphoric acid process

Process
Catalyst: Kieselguhr (phosphoric acid deposited on silica/alumina pellets)
Temperature: 491.49 K
Pressure: 2,758 kPa
Reactor: Vessel with beds of solid catalyst
Yield: 95% and 99.9% pure

Note
The reaction can be carried out with benzene and propylene in either the liquid or
vapor phase; the more common process is vapor phase.
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Donald L. Burdick, William L, Leffler, Petrochemicals in nontechnical language fourth edition, PennWell corporation, 2010.

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CUMENE PRODUCTION
2) The catalytic distillation process using zeolite

Process
- Benzene liquid is introduced at the top of the column and mixed in countercurrent with the propylene
vapor. Zeolite-based catalysts cause the direct alkylation of benzene with propylene and to form cumene.
Catalyst: Zeolite
Reactor: Main reactor (catalyst bed reactor) and distillation column
Purity: 99.9% purity

Note
One of the side reactions also produces an appreciable amount of polyisopropyl benzene (PIPB).
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Donald L. Burdick, William L, Leffler, Petrochemicals in nontechnical language fourth edition, PennWell corporation, 2010.

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CUMENE PRODUCTION
3) Monsanto-Lmmus Crest cumene production process

cumene production [homepage on the Internet]. 2014 [cited 20014 June 20]. Available from:
http://www.uop.com/cumene-qmax/

Process
Catalyst: Aluminum chloride and hydrochloric acid
Temperature: 403.15 408.15 K
Pressure: 340 350 kPa

Note
Aluminum chloride (AlCl3) is category of Friedel-Crafts type catalyst used to add alkyl
group to aromatic ring of benzene.
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Donald L. Burdick, William L, Leffler, Petrochemicals in nontechnical language fourth edition, PennWell corporation, 2010,

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CUMENE WORLD MARKET APPLICATIONS

Global cumene consumption [homepage on the Internet]. [cited 2014 July 21].
Available from: http://mcgroup.co.uk/researches/cumene

Main cumene applications include production of phenol and, further, acetone.


Europe, North America and Japan have been leading the market for quite a long time
but due to large capacity introductions in China, the Asia Pacific region came ahead.
The region also acts as the biggest consumer in the world market. China, South
Korea, Japan are among countries with considerable consumption volumes in Asia
Pacific.
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PHENOL

Specifications
Global
Production in
Thailand

500 (103 ton/year)

PTT Phenol

500

Source: Petroleum Institute of Thailand (PTIT)s


Industry Survey Version 1/2010 as of February 2014

Production
The major processes for producing Phenol
1. Cumene oxidation process

2. Alternate process technology

World market applications

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PHENOL SPECIFICATIONS
IUPAC name: Phenol
Other names: Carbolic acid, benzenol,
phenylic acid, hydroxybenzene, phenic acid

Properties
Molecular formula: C6H6 O
Molar mass: 99.11 g/mol
Appearance: Transparent crystalline solid
Density: 1.07 g/cm3
Melting point: 313.6 K
Boling point: 454.8 K
Solubility in water: 8.3 g/100 cm3 (293.15 C)
Acidity (pKa): 9.95 (in water)
Dipole moment: 17D

Hazards
Main hazards: Corrosive
Flash point: 352 K

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PHENOL PRODUCTION
1) Cumene oxidation process

Phenol production [homepage on the Internet]. [cited 2014 June 20].


Available from: http://nptel.ac.in/courses/103103029/module3/lec22/2.html

Process
Step 1 Oxidation of cumene to cumene hydro peroxide
Temperature: 383.15 394.26 K
Step 2 Cumene hydro peroxide decomposition using diluted sulfuric acid
Temperature: 338.71 352.6 K
Pressure: 172.4 344.75 kPa

Note
The effluent of from the acid treatment reactor contains about 60% phenol and 35%
acetone.
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Donald L. Burdick, William L, Leffler, Petrochemicals in nontechnical language fourth edition, PennWell corporation, 2010, p. 103-107

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PHENOL PRODUCTION
2) Alternate process technology
Indirect oxidation of benzene to phenol
- In the first, benzene is hydrogenated to cyclohexane, followed by a partial oxidation to
cyclohexanol. The cyclohexanol is then dehydrogenated to phenol.

Catalytic conversion of benzene


- Benzene is converted directly to phenol by a catalytic reaction with nitrous oxide.

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Donald L. Burdick, William L, Leffler, Petrochemicals in nontechnical language fourth edition, PennWell corporation, 2010.

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PHENOL WORLD MARKET APPLICATIONS

Global phenol consumption [homepage on the Internet]. [cited 2014 July 16].
Available from: http://mcgroup.co.uk/researches/phenol

Phenol is a chemical, mainly used for bisphenol-A (BPA) and phenolic resins production. These two
products are the main phenol markets today. The market is forecast to show stable growth and Asia
Pacific will be the main consumer (the same as it is today).
In other regions phenol demand is in decline. There are two main reasons for it. First, demand for the
phenol main derivative bisphenol-A is low. Second, the prices for benzene, raw materials for
producing phenol, are very high and rising. But Asia Pacific region, and particularly China, tries to
become more self-sufficient in terms of phenol imports and has planned a number of new capacity
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introductions by the end of decade.

PHENOLIC RESINS

Properties
Production

Applications

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PHENOLIC RESINS PROPERTIES


- Bonding Strength : Phenolic resin effortlessly penetrates and adheres to the structure of
many organic and inorganic fillers and reinforcements, which makes it an ideal candidate for
various end uses.
- High Temperature Resistance : A key characteristic of thermoset phenolic resin is its ability to
withstand high temperature under mechanical load with minimal deformation or creep.
- Chemical Resistance : Phenolic resins accommodate the harsh exposure of severe chemical
environments. Typical exposures include gasoline, alcohol, oil, glycol, brake fluid, various
hydrocarbons, and also weak acids and bases.
- Low Smoke and Toxicity : Burning phenolic resin typically generates hydrogen, hydrocarbons,
water vapor, and carbon dioxide. Phenolic resin produces a relatively low amount of smoke at
a relatively low level of toxicity.
- High Carbon and Char Yield : Phenolic resins demonstrate higher char yields than other
plastic materials when exposed to temperatures above their point of decomposition. In an
inert atmosphere at high temperatures (300 - 1,000 C), phenolic resin will convert to a
structural carbon known as vitreous carbon.

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PHENOLIC RESINS PRODUCTION


Phenol-formaldehyde resins or phenolic resins, as a group, are formed by a step-growth
polymerization of phenol with formaldehyde, the reaction can be either acid- or basecatalyst.

Processes
In aqueous solution, formaldehyde exists in equilibrium with methylene glycol.

Depending on the pH of the catalyst, these monomers react to form one of two general
resin types: NOVOLAC RESINS and RESOL RESINS.

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PHENOLIC RESINS PRODUCTION


Novolac Resins: An acidic catalyst (oxalic acid, hydrochloric acid or sulfonate acids.)and a molar
excess of phenol to formaldehyde are conditions used to make novolac resins. The following
simplified chemistry illustrates the wide range of polymers possible. The initial reaction is between
methylene glycol and phenol.

Note

The reaction continues with additional phenol, and splitting


off of water.

Hexamethylenetetramine
or
"hexamine" is a hardener added
to crosslink novolac. At a
temperature > 363.15 K , it forms
methylene and dimethylene
amino bridges. Because an
additional agent is required to
complete the resin's cure, the
industry commonly refers to
novolac resins as "two-stage" or
"two-step" products.

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PHENOLIC RESINS PRODUCTION


Resol Resins: A basic (alkaline) catalyst and, usually but not necessarily, a molar excess of
formaldehyde is used to make resol resins. The following two stages describe a simplified view of the
reaction: First, phenol reacts with methylene glycol to form methylol phenol.

Note
Methylol phenol can react with itself to form a longer chain
methylol phenolic:

or form dibenzyl ether:

or react with phenol to form a methylene bridge.

The most important point in


resol resin chemistry is that,
when an excess of formaldehyde
is used, a sufficient number of
methylol and dibenzyl ether
groups remain reactive to
complete the polymerization and
cure
the
resin
without
incorporation of a cure agent
such as hexa. For this reason, the
industry commonly refers to
resol resins as "single-stage" or
"one-step" type products.

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PHENOLIC RESINS APPLICATIONS


The unique ability of phenolic resin to "wet out" and to cross-link throughout the fillers and
reinforcements provides the means to engineer the desired mechanical, thermal, chemical and
abrasive resistant properties.
- Multiple applications benefit by using phenolic resins in the following composite part manufacturing
processes: resin transfer molding, pultrusion , profile extrusion, filament winding, hand lay-up.
- Phenolic resins provide exceptional resistance under all environmental conditions. Specific
applications are: Functional components used in visible areas, Below surface products used for
padding and sound absorption, Rigid parts used as substrate for decorative material.
- Phenolic foam has a unique set of properties such as excellent fire and heat resistance and a low
smoke and toxicity rating when burned. Typical application fields are: Floral foam (dry and wet foams),
Orthopedic foam (for making foot print casts), Insulating Foams.

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BISPHENOL A (BPA)

Specifications
Global
Production in
Thailand

280 (103 ton/year)

Bayer

280

Source: Petroleum Institute of Thailand (PTIT)s


Industry Survey Version 1/2010 as of February 2011

Production
World market applications

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BISPHENOL A (BPA) SPECIFICATIONS


IUPAC name: 4,4-(Propane-2,2-diyl)diphenol
Other names: BPA, p,p-isopropylidenebisphenol, 2,2bis(4-hydroxyphenyl)propane

Properties
Molecular formula: C15H16 O2
Molar mass: 1228.29 g/mol
Appearance: White solid
Density: 1.2 g/cm3
Melting point: 432 K
Boling point: 493 K
Vapor pressure: 5 *10-6Pa (25 C)

Hazards
Flash point: 500 K
Autoignition Temp : 873 K
LD50: 10,000 11,400 mg/kg

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BISPHENOL A (BPA) PRODUCTION

Process
Bisphenol compound is mainly synthesized by the condensation of acetone with two
equivalents of phenol. The reaction is catalyzed by a strong acid, such as hydrochloric
acid (HCl) or a sulfonated polystyrene resin. The reaction temperature is kept at about
338.71 K about 30 minutes.
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Donald L. Burdick, William L, Leffler, Petrochemicals in nontechnical language fourth edition, PennWell corporation, 2010.

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BISPHENOL A WORLD MARKET APPLICATIONS

Global bisphenol A consumption [homepage on the Internet]. [cited 2014 July 18].
Available from: http://mcgroup.co.uk/researches/bisphenol-a-bpa

Bisphenol A became quite a controversial chemical after it had been recognized as a


potentially harmful substance. The final conclusion about its safety has not been reached yet
though Food and Drug Administration (FDA) has recently confirmed BPA to be safe.

BPA consumption in North America and Western Europe slows down due to its ban in baby
bottles, children food packaging. The further growth is expected mostly from Asia Pacific,
especially from China, where some new BPA capacities are going to be introduced in next few
years. In 2013 major bisphenol A producers included Bayer, Sabic Innovative Plastics, Nan Ya
Plastics Corp, LG Chem Co, Mitsui Chemicals Inc, etc.
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POLYCARBONATE (PC)

Specifications

Production
The major process for producing Polycarbonates (PC)
1. The two step process of bisphenol A and sodium hydroxide
2. The free of phosgene and methylene chloride

Applications

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POLYCARBONATE (PC) SPECIFICATIONS

Properties
Molecular formula: (C16H18 O3)n
Apparent density: 1.20 g/cm3
Water absorption: 0.16 0.35 % (24 hr)
Limiting oxygen index: 25 - 27%
Melting Temp: 428 K
Glass transition Temp: 420.15 K
Upper working Temp: 388.15 403.15 K
Lower working Temp: 233 K
Specific heat gravity: 1.2 1.3 kJ/kg K

115

Mechanical Properties
Tensile modulus: 2,379 MPa
Tensile strength: 66 MPa
Tensile elongation: 100 %
Flexural strength: 93 MPa
Flexural modulus: 2379 MPa
Compressive Strength: 86 MPa
IZOD Notched Impact: 16 ft-lb/in
Chemical Resistance
Acid-concentrated: poor
Acid-dilute: good
Alcohols: good
Alkalis: good-poor
Grease & Oil: good-fair
Halogen: poor

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POLYCARBONATE (PC) PRODUCTION


1. The two step process of bisphenol A and sodium hydroxide

Process
The bisphenol A is reacted with sodium hydroxide to give a disodium salt of BPA. That is reacted with
phosgene to form the polycarbonate . The reaction takes place in methylene chloride, an inert solvent.

Note
Both methylene chloride and phosgene are toxic substances that are difficult to handle. Moreover, the
process generates a large quantity of water and the polycarbonate has to be carefully handled to
eliminate the chloride impurities, an environmental and health issue.
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Donald L. Burdick, William L, Leffler, Petrochemicals in nontechnical language fourth edition, PennWell corporation, 2010.

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POLYCARBONATE (PC) PRODUCTION


2. The catalytic reaction of BPA and diphenyl carbonate (DPC)

Process
The free of phosgene and methylene chloride, needed some breakthroughs to become
commercial. It come from the catalyzed reaction of BPA and diphenyl carbonate (DPC) to
form the polymer.

Note
Now DPC comes from a reaction of phenol with dimethyl carbonate , which itself comes from
a methanol /carbon monoxide/oxygen reaction.
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Donald L. Burdick, William L, Leffler, Petrochemicals in nontechnical language fourth edition, PennWell corporation, 2010.

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POLYCARBONATE APPLICATIONS
Applications
Polycarbonate provides exceptional transparency, impact strength, heat resistance, dimensional
stability and electrical properties, making it ideally suited to a wide range of applications.
Typical markets and applications Polycarbonate and PC alloys include
Optical

Electric and Electronic Parts

Automotive

Medical

Household Applications

Safety

Others

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XYLENE
o-Xylene
Global Thailand
production

66 (103 ton/year)

PTTAR

66

Specifications
Production

m-Xylene
Global Thailand
production

286 (103 ton/year)

IRPC

120

TPX

90

PTTAR

76

The major process for producing xylene


1. Catalytic Reforming
2. Stream cracking
3. Toluene Disproportionation (TDP)

Xylene separating process

p-Xylene
Global Thailand
production

2,149 (103 ton/year)

PTTAR

1,156

Exxon Mobil

504

PTTAR

489

1.

Cryogenic crystallization

2.

Molecular sieve adsorption

World market trend

Source: Petroleum Institute of Thailand (PTIT)s


Industry Survey Version 1/2010 as of February 2011

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XYLENE SPECIFICATIONS
Ortho-xylene

IUPAC name: o-Xylene


Systematic name: 1,2-Dimethylbenzene
Other names: o-Xylol, Orthoxylene
Thermochemistry
Phase behaviour
Solid, liquid, gas

Properties
Molecular formula: C8H10
Molar mass: 106.16 g/mol
Appearance: clear, colorless liquid
Density: 0.88 g/mL, liquid
Melting point: 248 K
Boling point: 417 K
Solubility in water: practically insoluble
Viscosity: 0.62 cP at 293.25 K

Hazards
Main hazards: Flamable
Flash point: 290 K

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XYLENE SPECIFICATIONS
Meta-xylene

IUPAC name: m-Xylene


Systematic name: 1,3-Dimethylbenzene
Other names: m-Xylol, 1,3-Dimethylbenzene
Thermochemistry
Phase behavior
Solid, liquid, gas

Properties
Molecular formula: C8H10
Molar mass: 106.16 g/mol
Appearance: clear, colorless liquid
Density: 0.86 g/mL, liquid
Melting point: 225 K
Boling point: 412 K
Solubility in water: practically insoluble
Viscosity: 0.812 cP at 293.15 K

Hazards
Main hazards: Flammable
Flash point: 298.15 K

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XYLENE SPECIFICATIONS
Para-xylene
IUPAC name: p-Xylene
Systematic name: 1,4-Dimethylbenzene
Other names: p-Xylol, Paraxylene

Thermochemistry
Phase behaviour
Solid, liquid, gas
Properties
Molecular formula: C8H10
Molar mass: 106.16 g/mol
Appearance: clear, colorless liquid
Density: 0.86 g/mL, liquid
Melting point: 286 K
Boling point: 411 K
Solubility in water: practically insoluble
Viscosity: 0.34 cP at 303.15 K

Hazards
Main hazards: Flamable
Flash point: 298.15 K

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XYLENE PRODUCTION
1. Catalytic Reforming

Processes

Catalytic reforming [homepage on the Internet]. [cited 2014 June 20]. Available
from: http://en.wikipedia.org/wiki/BTX_(chemistry)

Catalysts: Silica or Alumina coated with Platinum, Palladium, or Rhodium


Temperature: 426.76 783.15 K
Pressure: 1,378.95 5,515.80 kPa
Reaction time: 30 minutes

Note
- An important by-product of reforming operations is hydrogen, which reacts with
carbon depositing on the catalyst to form methane.
- The reformate stream, high in octane as it is, makes an excellent gasoline blending
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component.

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XYLENE PRODUCTION
2. Steam Cracking

Steam Cracking [homepage on the Internet]. [cited 2014 June 20].


Available from: http://www.2b1stconsulting.com/propylene/

Processes
- Steam cracking is the process for producing ethylene and other alkenes from aliphatic
hydrocarbons. Depending on the feedstock used to produce the olefins, steam cracking can produce
a benzene-rich liquid by-product called pyrolysis gasoline. Pyrolysis gasoline can be blended with
other hydrocarbons as a gasoline additive, or routed through an extraction process to recover BTX
aromatics (benzene, toluene and xylenes
Temperature: > 1199.82 K

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XYLENE PRODUCTION
3. Toluene Disproportionation (TDP)

Toluene benzene

Toluene Disproportionation[homepage on the Internet]. [cited 2014 June 20].


Available from: http://www.exxonmobilchemical.com

Process
-

The toluene disproportionation process, a methyl group leaps off one toluene molecule
(and it replaced by hydrogen) and attaches itself to another toluene molecule (replacing
by hydrogen atom). That leaves one benzene molecule and one xylene molecule.
Effective catalyst include some of the noble metals, specifically Pt and Pd deposited on
alumina pellets.
The reactor operate at temperature from 923.15 K to 1,223.15 K and pressure ranging
from 1,034.21 kPa to 3,447.37kPa.
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XYLENE SEPARATION
1. Cryogenic crystallization
Components

Boiling point (F)

Freezing point (F)

Benzene

176.2

41.9

Toluene

231.4

-138.9

Ethybenzene

277.1

-138.0

Paraxylene

281.0

55.9

Metaxylene

282.4

-54.2

Orthoxylene

292.0

-13.0

Process
- The orthoxylene and ethybenzene split out in fractionator.
- The mixed para-and metaxylenes are processed in a fashion in order to get the
grease out of gravy.
- The mixed para- and metaxylene are cooled initially to about 205.45 K.
- The paraxylene is crystallized and grow in a liquidsolid mixture.

Note
- The key to good solid-liquid separation in the next step is crystal size . The
larger the paraxylene crystal, the better the separation.
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Donald L. Burdick, William L, Leffler, Petrochemicals in nontechnical language fourth edition, PennWell corporation, 2010.

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XYLENE SEPERATION
2. Molecular sieve adsorption

Process
- The mixed para and metaxylene are pumped into a fixed bed of
molecular sieve pellets.
- The effluent stream coming out of the vessel is mostly metaxylene.
- The sieves are selectively adsorbing the paraxylene
- The paraxylene is back flushed out of the sieves using a desorbent.
- Paraxylene from this technique is about 99.5 % pure.
Note
- After the desorption, the sieve bed is heated to drive our any remaining
paraxylene and toluene, the cycle is ready to begin again.
Donald L. Burdick, William L, Leffler, Petrochemicals in nontechnical language fourth edition, PennWell corporation, 2010.

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XYLENE WORLD MARKET TREND

Global o-xylene consumption [homepage on the Internet]. [cited 2014 July 20].
Available from:http://mcgroup.co.uk/researches/orthoxylene-ox

O-xylene is one of the most popular isomers of xylene. Almost all o-xylene, produced by the
companies, is used for preparation of phthalic anhydride, which is then used in polyester resins
production. Today phthalic anhydride production accounts for nearly 90% of global OX
consumption. Global demand for the o-xylene stands at a high level. After the global economic
crisis, the situation on the product market has quickly returned to normal. In near future the market
will be driven mainly by Asia Pacific region, while Europe and North America wont show any
noticeable growth.
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XYLENE WORLD MARKET TREND

Global p-Xylene consumption [homepage on the Internet]. [cited 2014 July 20].
Available from:http://mcgroup.co.uk/researches/orthoxylene-ox

Main end-users of p-xylene are manufacturers of purified terephthalic acid (PTA) and dimethyl
terephthalate (DMT). Global demand for the p-xylene remains at a high level. After the global
economic crisis, the situation on the market of the product quickly returned to normal. Global
PX market is expected to grow at about 5% per year in near future.
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XYLENE WORLD MARKET TREND

Xylene world market trend [homepage on the Internet]. [cited 2014 June 20]. Available from: http://www.ogj.com/articles/print/volume-95/issue2/in-this-issue/gas-processing/ethylene-consumption-seen-doubling-by-2015.html

Demand for p-Xylene and o-Xylene is expected to grow at a higher rate than benzene
demand. Explosive growth that polyester markets enjoyed during the past 10 years has
had a dramatic effect on the markets for p-Xylene and mixed xylenes. p-Xylene demand
growth is expected to drop only to less than 5%/year on a world basis after 2010.
Overall mixed xylene demand will grow to 50 million tons by 2015 from 18.5 million tons in
1995, the study predicts.

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PHTHALIC ANHYDRIDE (PA)

Specifications
Global
Production in
Thailand

50 (103 ton/year)

Continental
Petrochemical

50

Source: Petroleum Institute of Thailand (PTIT)s


Industry Survey Version 1/2010 as of February 2011

Production
World market applications

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PHTHALIC ANHYDRIDE (PA) SPECIFICATIONS


IUPAC name: 2-benzofuran-1,3-dione
Other names: Isobenzofuran-1,3-dione
Hazards
Main hazards: effect on dry skin, but burns wet skin
Flash point: 425 K
Properties
Molecular formula: C8H4O3
Molar mass: 148.1 g/mol
Appearance: white flakes
Density: 1.53 g/cm3
Melting point: 404.75 K
Boling point: 568.15 K
Vapor pressure: 0.685 kPa at 298.15 K

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PTHALIC ANHYDRIDE (PA) PRODUCTION


Oxidation of o-xylene

Process
-

Hot o-xylene is mixed with excess preheated air in a ratio of 20:1 air to xylene by weight.
The gaseous mixture is then fed to the reactor with vanadium pentoxide catalyst on silica gel.
The reaction take place at 699.82 810.93 K.
Phathalic anhydride solidifies at 1084.08 K, achieving purify of 99.5 %.

Note
- The reaction is exothermic, and the heat of reaction must be removed from the tubes to maintain
the reaction temperature.
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Donald L. Burdick, William L, Leffler, Petrochemicals in nontechnical language fourth edition, PennWell corporation, 2010.

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PTHALIC ANHYDRIDE WORLD MARKET APPLICATIONS

(DOP)
Global PA consumption [homepage on the Internet]. [cited 2014 July 21].
Available from: http://mcgroup.co.uk/researches/pthalic anhydride

Phthalic anhydride (PA) market has reached pre-crisis growth levels and in the next few years
is expected to grow at more than 3% per year. However, some plasticizers manufacturers are
considering switching their production capacities to non-phthalate products, so the forecast
can be less optimistic.
Generally, world PA demand is driven by such end-use applications as plasticizers, dyes, resins
and etc. In 2013 phthalates and unsaturated polyester (UPE) resins were the largest end-uses
for PA. Today main phthalic anhydride consumer is Asia Pacific region, followed by Europe. But
in near future Latin America together with Asia Pacific region are expected to become leaders
in global PA consumption.
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ALKYD RESIN

Properties

Production
Applications

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ALKYD RESIN PROPERTIES


Alkyd coatings are typically sold in three classes: long, medium, and short. These terms represent
the oil length in the resin.
Long Oil Alkyd Resins
Length of oil (oil percentage) is more than 55 in alkyd resins formulations. Long oil alkyds have a
high percentage of drying oil content.
Medium Oil Alkyd Resins
The percentage of oil in alkyd resins is between 45-55. Medium oil alkyds have less drying oil and
have a higher percentage of large molecular weight polymer backbone.
Short Oil Alkyd Resins
The percentage of oil in alkyd resin is less than 45.The percentage of drying oil is very low in
relation to the base alkyd polymer chain.

Properties of alkyd resins


- Very good film-forming properties.
- Good adhesion of the paint products manufactured with their use to most materials used in
the building industry: metal, wood and wood-based materials, cement plasters, cement-lime
plasters, gypsum, gypsum cardboards and even to stone, concrete and other such materials;
- Resistance to external factors, and especially to UV radiation, precipitations, also within the
relatively broad temperature range.

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ALKYD RESIN PRODUCTION

Process
Alkyd resins are produced by reacting a polybasic acid (phthalic anhydride, maleic anhydride, etc.)
with a polyhydric alcohol (glycerine, pentaerythritol, ethylene glycol, etc.) and an oil or a fatty acid.
The reaction may be further modified with the addition of rosin and/or phenol-formaldehyde resin.
Various polybasic acids, polyhydric alcohols, oils, fatty acids and modifying agents may be combined
to produce alkyds with specifically desired properties.

Note
These products were too brittle to make satisfactory coatings. The use of oils or unsaturated fatty
acids in combination with the brittle alkyds resulted in the air-drying coatings which revolutionized
the chemical coating industry. Further developments led to the use of completely or partially
saturated oils and fatty acids for baking finishes and lacquers.
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Applications

ALKYD RESIN APPLICATIONS

These resins are useful as film forming agents in paint, varnished and enamels & as
thermosetting plastics that can be molded into solid objects. The application depending on the
characteristic of each resin types.
Resin Type

Solvent

Characteristics and Applications

Short-oil fatty acid


Alkyd resin

Xylene

Short-oil fatty acid Alkyd resin. Quick-drying, high hardness. Apply to


PU paint, wood lacquer, metal paint.

fatty acid Alkyd resin

Xylene

Fatty acid Alkyd resin. Apply to antiseptic paint

Short-oil fatty acid


Alkyd resin

Xylene

Short-oil fatty acid Alkyd resin. Light colored, high gloss, high
hardness. Apply to PU paint, Amino baking paint, nitro lacquer.

Short-oil castor oil


Alkyd resin

Xylene

Short-oil castor oil alkyd resin. Good miscibility with pigment, good
brushing, good flexibility, good fullness, good gloss. Apply to baking
varnish, NC spray paint, PU paint.

Short-oil castor oil


Alkyd resin

Xylene

Short-oil castor oil Alkyd resin. Good miscibility with pigment.


Pigment shallow. Apply to nitro lacquer, PU wood paint, metal paint.

Coconut oil acid Alkyd


resin

xylene

Coconut oil acid alkyd resin. High gloss, good miscibility with
pigment. Pigment shallow. Apply to Amino baking paint, nitro
lacquer.

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Application of Alkyd resin [homepage on the Internet]. [cited 2014 July 29]. Available from: http://http://www.shengjia-resin.com/cp08.Asp

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UNSATURATED POLYESTER

Properties
Production

Applications

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UNSATURATED POLYESTER PROPERTIES

Depending on the reactants, unsaturated polyester has a variety of a chemical structure and
it can be both thermoplastic and thermoset.

Properties
The nature of the Unsaturated Polyester means that physical properties are dependent on the
additional materials used, and the conditions of curing, for a specific application. With such
variety available it is best to refer to manufacturers for performance of individual grades.

Resistance to chemical
Dilute Acid
Dilute Alkalis
Oils and Greases
Aliphatic Hydrocarbons
Aromatic Hydrocarbons
Halogenated Hydrocarbons
Alcohols

good
good
moderate
poor
poor
poor
good
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UNSATURATED POLYESTER PRODUCTION

Process
Unsaturated polyesters formed by the reaction of polyols (also known as polyhydric alcohols),
organic compounds with multiple alcohol or hydroxy functional groups, with saturated or
unsaturated dibasic acids. Typical polyols used are glycols such as ethylene glycol; acids used are
phthalic acid and maleic acid. An example reaction for produce Unsaturated polyesters is showed
above.

Note
Unsaturated polyesters is thermosetting, cure exothermically. The use of excessive catalyst can
cause charring or even ignition during the curing process. Excessive catalyst may also cause the
product to fracture or form a rubbery material.
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UNSATURATED POLYESTER APPLICATION


Applications

Unsaturated polyester (UP) Resins are widely used in a host of applications where
advantage may be taken of their good range of mechanical properties, corrosion
resistance and low weight.
- Un-reinforced and reinforced versions are most commonly used for clear casting
resins, coatings, buttons, body fillers, work-surfaces (such as polyester marble),
polyester concrete (for applications such as road drainage) and in the manufacture of
Gel Coats (applied to composite materials to improve the surface finish).

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DIOCTYL PHTHALATE (DOP)

Specifications
Production
Applications

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DIOCTYL PHTHALATE (DOP) SPECIFICATIONS


IUPAC name: Bis(2-ethylhexyl) phthalate
Other names: Di-2-ethylhexyl phthalate,
Diethylhexyl phthalate (DEHP), Dioctyl
Phthalate (DOP)
Properties
Molecular formula: C24H38 O4
Molar mass: 390.56 g/mol
Melting Temp: 223.15 K
Boiling point: 658.15 K
Dioctyl phthalate (DOP, DEHP), is clear, colourless, viscous liquid with a slight,
characteristic odor. Soluble in ethanol, ether, mineral oil and the majority of organic
solvents. Immiscible with water, resistant to hydrolysis and air oxygen activity.

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DIOCTYL PHTHALATE (DOP) PRODUCTION

DOP production process [homepage on the Internet]. [cited 2014 July 16].
Available from: http://www.psenterprise.com/gproms/applications/batch/

Process
Industrial production entails the reaction of phthalic anhydride with 2-ethylhexanol:
C6H4(CO)2O + 2 C8H17OH C6H4(CO2 C8H17)2 + H2O

Note
DOP is chiral, and the resultant consists of a mixture of (R,R)-, (S,S)-, and (R,S)-isomers.
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DIOCTYL PHTHALATE (DOP) APPLICATIONS


Plastic Industry
Dioctyl phthalate can be used as a softening agent , such as to make the product
easier to rebound and harder to undergo form change under pressure, without
affecting of the plastics. DOP possesses its good plasticizing properties. It is
extensively used in processing polyvinyl choride and ethylcellulose to produce plastic
film, imitation leather, electric wire, cable wearer, sheet, planet, mould plastic
products and used in nitrocellulose . It has the applications in the industry of
automotive, and , flooring.
Medical Devices
Dioctyl phthalate is used a plasticiser in the manufacture of medical and , such as
blood bags and dialysis equipment. It has a further and unique role in blood bags
because it actually helps to prolong the life of the blood itself

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POLYESTER POLYOLS

Specifications
Production
Applications

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POLYESTER POLYOLS SPECIFICATIONS


Typical properties of polyesters polyols depending on elementary and raw
material useing.
Component and
Structure

adipic
acid,
diethylene
glycol,
trimethylo
l propane

adipic acid
phthalic acid,
1,2-propylene
glycol,
glycerine

adipic acid,
phthalic
acid, oleic
acid,
trimethylol
propane

adipic acid,
ethylene
glycol,
diethylene

adipic acid,
ethylene
glycol, 1,4butane diol

adipic
acid,
diethylene
glycol

phthalic
acid, maleic
acid,
trimethylol
propane

Average MW

2400

1000

930

2000

2000

2750

2450

OH number
(mgKOH/g)

57-63

205-221

350-390

58-62

52-58

38-45

250-275

OH content
(meq/g)

1.1

3.8

6.6

1.1

1.0

0.7

4.6

*Average
funtionality

2.7

3.8

6.2

2.1

2.0

2.0

11.3

Viscosity at
348.15 K (mPa.s)

950-1100

570-750

1300-1500

500-700

500-600

700-800

Pour point (C)

261.15

261.15

266

290 - 329

322 - 325

264

363 - 273

Density at
348.15 K (g/L)

1.15

1.15

1.1

1.15

1.17

1.12

1.24

*Average functionality = PM x OH content (meq/g) / 1000


Typical properties of polyesters polyols [homepage on the Internet]. [cited 2014 July 16].
Available from: http://www.poliuretanos.com.br/Ingles/Chapter1/15Polyester.htm

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POLYESTER POLYOLS PRODUCTION

Process
-

The diol (propylene glycol) is first heated in an inert atmosphere (under the blanket of
nitrogen) to 304.93 K 366.48 K
The dicarboxylic acid (Phthalic acid) is added and further heat applied to 422.04 477.6 K.
The conversion rate s are 99+%, with yields of 85%

Note
- The co-product, water is continuously drawn off as it is produced by the condition reaction to
favor the formation of the polymer.

Donald L. Burdick, William L, Leffler, Petrochemicals in nontechnical language fourth edition, PennWell corporation, 2010.

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POLYESTER POLYOLS APPLICATIONS


Polyester polyols were the first polyols used in the beginning of PU development,
and are produced by polycondensation of a diacid with excess diol . The most used
acids are adipic and phthalics.
- Adipic acid based polyester polyols are used in applications where flexibility is
wanted, as in flexible foams and elastomers.

- Phthalic acids (or phthalic anhydride) based polyols, have rigid chains and are
used in rigid foams and in high performance coatings.

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TEREPHTHALIC ACID

Specifications

Production
Global
Production in
Thailand

1,277 (103 ton/year)

Siam Mitsui

1,440

Indorama

700

TPT

520

World market applications

Source: Petroleum Institute of Thailand (PTIT)s


Industry Survey Version 1/2010 as of February 2011

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TEREPHTHALIC ACID SPECIFICATIONS


IUPAC name: Terephthalic acid
Other names: Benzne-1,4-dicarboxylic
acid, para-Phthalic acid,TPA,PTA,BDC

Properties
Molecular formula: C8H6O4
Molar mass: 166.13 g/mol
Appearance: white crystals or powder
Density: 1.522 g/cm3
Melting point: 573.15 K
Boling point: sublimes
Acidity: 3.51 pKa

Hazards
Auto-Ignition Temp: 768.15 K
Flash points: Open cup, 533.15 K
Flammable limits: Not available.
Product of combustion: CO, CO2
Flamability o fthe product: Maybe
combustible at high temperature.

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TEREPHTHALIC ACID PRODUCTION

Terephthalic acid production process [homepage on the Internet]. [cited 2014 July
16]. Available from: http://www.lotte-ppta.com/process.htm

Process
-

The reaction takes place in the liquid phase in an acetic acid solvent at 477.6 K and 1,378.98
kPa, with a cobalt acetate / manganese acetate catalyst and sodium bromide promoter.
The reaction time is about one hour Yield are 90 % - 95 %.

Note
-

Solid TPA has only limited solubility in acetic acid, so happily the TPA crystal drop out of
solution as they form.
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The crude TPA is purified by aqueous methanol extraction that gives 99+% pure.

TEREPHTHALIC WORLD MARKET APPLICATIONS

Global terephthalic acid consumption [homepage on the Internet]. [cited 2014 July 25].
Available from: http://mcgroup.co.uk/researches/bisphenol-a-bpa

Global terephthalic acid demand mainly depends on consumption of polyester fibers and PET
bottle resin across the globe. In 2013 these two applications accounted for 93 % of global
product demand.
Today China maintains its position as a leader in terephthalic acid production but it still has to
import large quantities of TPA to meet domestic demand. To change this situation China is going
to introduce new TPA production capacities in next few years. Other main producers are also
located in Asia Pacific region and include South Korea, Thailand and etc.
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POLY(ETHYLENE TEREPHTHALATE) (PET)

Specifications
Production
Applications

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POLY(ETHYLENE TEREPHTHALATE) (PET) SPECIFICATIONS


Mechanical Properties
Tensile modulus: 2 4 MPa
Tensile strength: 80 MPa
Tensile elongation: 60 165 %
Izod impact strength: 13 35 J/m
Coefficient of friction: 0.2 0.4

Properties
Molecular formula: (C10H8 O4)n
Apparent density: 1.38 g/cm3
Melting Temp: 533.15 K
Boiling Temp: > 623.15 K (decomposes)
Specific heat capacity: 1.0kJ/(kg.K)
Thermal conductivity: 0.15 - 0.24 W m-1K-1

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POLY(ETHYLENE TEREPHTHALATE) (PET) PRODUCTION

PET production process [homepage on the Internet]. [cited 2014 July 18].
Available from: http://www.hitachi.com/businesses/infrastructure/product_site/ip/process/pet.html

Process
In the terephthalic acid process, esterification of ethylene glycol and terephthalic acid is conducted
directly at moderate pressure (270 550 kPa) and high temperature (493.15 533.15 K).

Note
-

Water is eliminated in the reaction, and it is also continuously removed by distillation.


Production of polyethylene terephthalate(PET) with little diethylene glycol as a byproduct.
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POLY(ETHYLENE TEREPHTHALATE) (PET) APPLICATIONS


Polyethylene terephthalate (PET) is a hard, stiff, strong, dimensionally stable material that absorbs
very little water. It has good gas barrier properties and good chemical resistance except to alkalis
(which hydrolyze it). Its crystallinity varies from amorphous to fairly high crystalline. Polyethylene
terephthalate (PET) can be highly transparent and colorless but thicker sections are usually
opaque and off-white.

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POLY(BUTYLENE TEREPHTHALATE) (PBT)

Specifications
Production

Applications

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POLY(BUTYLENE TEREPHTHALATE) (PBT) SPECIFICATIONS

IUPAC name: Poly(oxy-1,4-butanediyloxycarbonyl1,4-phenylenecarbonyl)

Properties
Molecular formula: (C12H12 O4)n
Apparent density: 1.38 g/cm3
Melting Temp: 496.15 K
Deflection Temp: 438.15 493.15 K
Glass fiber content: 0 40 %

Mechanical Properties
Tensile strength: 80 MPa
Tensile elongation: 60 165 %
Flexural strength: 74.1 227.24 MPa

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POLY(BUTYLENE TEREPHTHALATE) (PBT) PRODUCTION

DOP production process [homepage on the Internet]. [cited 2014 July 18]. Available from:
http://www.hitachi.com/businesses/infrastructure/product_site/ip/process/pet.html

Peter D Phelps., and Gary R Faler., (2010) Solution polymerization of butanediol


and dimethyl terephthalate in the presence of a catalyst. U.S. Patent 7767781 B2.

Process
Polybutylene terephthalate(PBT) process technology achieves by polycondensation reactions of
1-4-Butylene glycol with PTA or PBT at low temperatures.

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POLY(BUTYLENE TEREPHTHALATE)(PBT) APPLICATIONS


Polybutylene Terephthalate (PBT) is a semi-crystalline, white or off-white polyester similar in both
composition and properties to polyethylene terephthalate (PET). It has somewhat lower strength
and stiffness than polyethylene terephthalate, PET, is a little softer but has higher impact strength
and very similar chemical resistance. It is employed in external and functional pieces in various
electrical and electronic system found in vehicles, windshield wiper arms, door handle, headlamp
bezels, connectors, capacitors, plugs and so on.

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AROMATIC POLYAMIDE

Specifications and Properties

Production
Applications

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AROMATIC POLYAMIDE PROPERTIES

General Properties
- good resistance to abrasion
- good resistance to organic solvents
- nonconductive
- no melting point, degradation starts from 773.15 K
- low flammability
- good fabric integrity at elevated temperatures
- sensitive to acids and salts
- sensitive to ultraviolet radiation
- prone to static build-up unless finished
- high Young's modulus
- high tenacity
- low creep
- low elongation at break (~3.5%)
- difficult- to dye usually solution dyed
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AROMATIC POLYAMIDE PRODUCTION

Process
Aromatic polyamide is synthesized in solution from the monomers of
phenylenediamine (para or meta) and terephthaloyl chloride in a condensation
reaction yielding hydrochloric acid as a by-product.

Note
Hexamethylphosphoramide (HMPA) was the solvent initially used for the
polymerization, but for safety reasons, DuPont replaced it by a solution of N-methylpyrrolidone and calcium chloride.
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AROMATIC POLYAMIDE APPLICATIONS


Poly(amide)s, usually known as polyamides, are polymers incorporating the amide group in their
repeating unit. The synthetic aromatic polyamides differ from the aliphatic polyamides (nylons) on
the highly aromatic nature of the polymer backbone. Both nylons and aromatic polyamides are
considered engineering materials, but the aromatic structure of the main chain of the aramids
endow this polymers with specialty characteristics making them less sensitive to oxidation, higher
solvent resistant, and conferring the materials with superior thermal and mechanical resistance,
five time stronger than steel, thus being classified as high-performance materials.

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DIMETHYL TEREPHTHALATE

Specifications
Production

Applications
World market applications

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DIMETHYL TEREPHTHALATE SPECIFICATIONS


IUPAC name: Dimethyl terephthalate
Systematic name: 1,4-Dimethyl benzene-1,4-dicarboxylate
Other name: 1,4-Benzenedicarboxylic acid, dimethyl
ester,Dimethyl 4-phthalate,Dimethyl-p-phthalate,Di-Me
terephthalate

Properties
Molecular formula: C10H10 O4
Molar mass: 194.18g/mol
Appearance: white solid
Apparent density: 1.2 g/cm3
Melting Temp: 415.15 K
Boiling point: 561.15 K
Acidity: -7.21pKa
Basicity: -6.60 pKa

Hazard
Flash point: 424.15 K
Possibility of hazard reaction: Able to decompose at
elevated temperatures.
Condition to avoid: heat, spark , and flames
Incompatible material: Strong oxidizing agent.
Decomposition product: CO and CO2

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DIMETHYL TEREPHTHALATE PRODUCTION

DMT production process [homepage on the Internet]. [cited 2014 July 16].
Available from: http://www.hitachi.com/businesses/infrastructure/product_site/ip/process/pet.html

Process
The Dimethyl Terephthalate (DMT) process, the esterification is done by feeding a slurry of TPA
crystal in methanol to a reactor with a catalyst of sulfuric acid at 377.6 K and 344.74 kPa.

Note
DMT forms and can be purified by distillation . Yield excess 95%, base on the TPA that ends up
as DMT.
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DIMETHYL TEREPHTHALATE APPLICATIONS


Dimethyl terephthalate (DMT) is used in the production of polyesters, including
polyethylene terephthalate (PET), polytrimethylene terephthalate (PTT), and
polybutylene terephthalate (PBT). It consists of benzene substituted with
carboxymethyl groups (CO2CH3) at the 1 and 4 positions. Because DMT is volatile,
it is an intermediate in some schemes for the recycling of PET, e.g. from plastic
bottles.
Hydrogenation of DMT affords the diol cyclohexanedimethanol, which is a useful
monomer

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DIMETHYL TEREPHTHALATE WORLD MARKET APPLICATION

Global DMT consumption [homepage on the Internet]. [cited 2014 July 22].
Available from: http://mcgroup.co.uk/researches

Dimethyl terephthalate (DMT) is a feedstock for polyethylene terephthalate (PET) and


polybutylene terephthalate (PBT) production. Other chemicals that can be produced with the help
of DMT include: terephthaldehyde, benzocaine, terephthalamide, terephthalohydroxamic acid,
etc.
Over the last few years dimethyl terephthalate market has been gradually decreasing because
more economical substitutes (such as PTA-based polymers) are gaining market shares. Today Asia
Pacific dominates dimethyl terephthalate market, with Japan, China and South Korea having the
majority of production capacity in the region.
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ISOPHTHALIC ACID

Specifications
Production

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ISOPHTHALIC ACID SPECIFICATIONS


IUPAC name: Isophthalic acid
Other name: Benzene-1,3-dicarboxylic acid
meta-Phthalic acid

Properties
Molecular formula: C6H4 (COOH)2
Molar mass: 166.14 g/mol
Appearance: white crystalline solid
Apparent density: 1.526 g/cm3
Melting Temp: 618.15 621.15 K
Decomposition Temp: > 646.15 K
Acidity: 3.46 pKa

Hazard
Auto ignition Temp : 923.15 K
No significant hazard identified for :
eye, skin, and inhalation however, use
protection is good.

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ISOPHTHALIC ACID PRODUCTION

Process
Isophthalic acid is produced on the billion kilogram per year scale by oxidizing meta-xylene using
oxygen. The process employs a cobalt-manganese catalyst.

Note
chromic acid can be used as the oxidant. It also arises by fusing potassium meta-sulphobenzoate,
or meta-brombenzoate with potassium formate (terephthalic acid is also formed in the last case).

Donald L. Burdick, William L, Leffler, Petrochemicals in nontechnical language fourth edition, PennWell corporation, 2010.

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DIPHENYL ISOPTHALATE

Specifications
Production
Applications

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DIPHENYL ISOPTHALATE SPECIFICATIONS


Common name: Diphenyl isophthalate
Other name: 1,3-Benzene Dicarboxylic Acid,
Diphenyl Ester

Properties
Molecular formula: C20H14 O4
Molar mass: 318.33 g/mol
Appearance: White crystalline solid
Odor: aromatic
Physical state: Solid
Boiling Point: > 553.15 K
Melting point: 414.15 415.15 K

Hazard
Flash point: 423.15 K
Fire and Explosion:
1. Slight fire hazard when exposed to
heat or flame.
2. Combustion products may include
toxic oxides of carbon.

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DIPHENYL ISOPTHALATE PRODUCTION

SnO

+
523.15 - 573.15 K

Process
Diphenyl isophthalate is prepared by reacting isophthalic acid with diphenyl carbonate in the
presence of stannous oxide (SnO) as the catalyst at a temperature of about 523.15 - 573.15 K
for 30 minutes to several hours depending on the temperature.

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DIPHENYL ISOPTHALATE APPLICATION


It is a monomer of PBT heat-resistant polymer and used as plasticizers of
Nylon resins. Besides, it also can be used as raw materials for aromatic
heterocyclic polymer and toughening polyamide engineering plastics.

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TOLUENE
Specifications

Production
Global Thailand
production

474 (103 ton/year)

TPX

144

IRPC

130

ROC

70

MOC

70

Xylene seperating process

PTTAR

60

1.

Source: Petroleum Institute of Thailand (PTIT)s


Industry Survey Version 1/2010 as of February 2011

The major process for producing toluene


1. Catalytic Reforming
2. Stream cracking

Azeotropic distillation

World market trend

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TOLUENE SPECIFICATIONS
IUPAC name: Methylbenzene
Other names: toluene, phenylmethane,
toluol, Anisen

Thermochemistry
Phase behaviour
Solid, liquid, gas
Properties
Molecular formula: C7H8
Molar mass: 92.14 g/mol
Appearance: colorless liquid
Density: 0.87 g/cm3, liquid
Melting point: 178 K
Boling point: 383.95 K
Viscosity: 0.59 cP at 293.15 K

Hazards
Main hazards: Highly Flamable
Flash point: 279.15 K

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TOLUENE PRODUCTION
1. Catalytic Reforming

Processes

Catalytic reforming [homepage on the Internet]. [cited 20014 June 20].


Available from: http://en.wikipedia.org/wiki/BTX_(chemistry)

Catalysts: Silica or Alumina coated with Platinum, Palladium, or Rhodium


Temperature: 699.82 783.15 K
Pressure: 1,378.95 5,515.80 kPa
Reaction time: 30 minutes

Note
- An important by-product of reforming operations is hydrogen, which is react with carbon
depositing on the catalyst to form methane.
- The reformate stream, high in octane as it is, makes an excellent gasoline blending
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component.

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TOLUENE PRODUCTION
2. Steam Cracking

Steam Cracking [homepage on the Internet]. [cited 2014 June 20].


Available from: http://www.2b1stconsulting.com/propylene/

Processes
- Steam cracking is the process for producing ethylene and other alkenes from aliphatic
hydrocarbons. Depending on the feedstock used to produce the olefins, steam cracking can produce
a benzene-rich liquid by-product called pyrolysis gasoline. Pyrolysis gasoline can be blended with
other hydrocarbons as a gasoline additive, or routed through an extraction process to recover BTX
aromatics (benzene, toluene and xylenes
Temperature: > 1199.82 K

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TOLUENE SEPERATION
Azeotropic distillation

Processes
-In this process for toluene, the solvent is methyl ethyl ketone and water (10%). When solvent
and toluene concentrate are mixed, the solvent and the naphthenes and parafins form an
azeotrope that boil about -6.67 C lower than their normal boiling temperature.
- In a fractionator, all azeotrope comes out the top as vapor. The toluene comes out the
bottom as a liquid.
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Donald L. Burdick, William L, Leffler, Petrochemicals in nontechnical language fourth edition, PennWell corporation, 2010

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TOLUENE WORLD MARKET TREND

Global Toluene consumption [homepage on the Internet]. [cited 2014 July 22].
Available from: http://mcgroup.co.uk/researches/toluene

Benzene and xylenes account for more than a half of toluene consumption. Demand for
toluene has been growing recently with higher rates in benzene, mixed xylenes and paraxylene sectors and lower one in toluene diisocyanate (TDI) production. Demand from
solvents sector was moderate.

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TOLUENE WORLD MARKET TREND

U.S. total toluene demand [homepage on the Internet]. [cited 2014 August 20].
Available from: http://www.ogj.com/articles/print/volume-96/issue-13/in-this-issue/general-interest/ustoluene-mixed-xylene-and-paraxylene-demands-to-see-steady-growth.html

The forecast for U.S. demand growth for toluene is at an annual rate of 1.5% between 1995
and 2015, from 1,338 million gal to 1,784 million gal. Growth in 1995-2005 is expected to be
1.3%, while growth in 2005-2015 is estimated to be slightly higher, 1.6% annually.
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TOLUENE DIISOCYANATE (TDI)

Specifications

Production
World market applications

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TOLUENE DIISOCYANATE SPECIFICATIONS


IUPAC name: 2,4-Diisocyanato-1-methyl-benzene
Other names: Tolylene diisocyanate, Methyl phenylene
diisocyanate

Thermochemistry
Phase behaviour
Solid, liquid, gas
Properties
Molecular formula: C9H6 N2O2
Molar mass: 174.2 g/mol
Appearance: colorless to pale yellow, liquid
Density: 1.214 g/cm3, liquid
Melting point: 259.05 K
Boling point: 524 K
Solubility in water: reacts

Hazards
Flash point: 400.15 K
Auto-Ignition Temp: 893.15 K
Product of combustion: CO, CO2,NO, NO2

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TOLUENE DIISOCYANATE PRODUCTION

Process
Most of the TDI commercially produced today come from phosgenation routes
following the step of:
- Nitration of toluene to give dinitrotoluene.
- Hydrogenation of dinitrotoluene to give the diamine (with NH2 signature groups).
- Phosgenation of diamine to give TDI.

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Donald L. Burdick, William L, Leffler, Petrochemicals in nontechnical language fourth edition, PennWell corporation, 2010.

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TOLUENE DIISOCYANATE WORLD MARKET APPLICATIONS

Global TDI consumption [homepage on the Internet]. [cited 2014 July 20].
Available from: http://mcgroup.co.uk/researches/toluene diisocyanate-tdi

Toluene Diisocyanate (TDI), is mainly used in the manufacture of polyurethane (PU) flexible
foams; this end use sector accounted for 87% of global TDI demand in 2013. Other applications
include rigid foams, adhesives, sealants and surface coatings and elastomers.
The leading producer of TDI is China; other large producers include USA, Japan, South Korea
and Germany. The largest consumer is the Asia Pacific region, followed by Europe and North
America. In near future TDI market growth will be mainly provided by Asia Pacific region.
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POLYURETHANE

Properties
Production
Applications

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POLYURETHANE PROPERTIES
Advantages and Characteristics of polyurethane
Injected Polyurethane is light, very rigid and has a density of between
35kg/m and 60kg/m
Thermal conductivity of between 0.018 W/m.K to 0.023 W/m.K
Excellent acoustic and vibration resistant properties
Resistant to most chemicals, particularly hydrocarbons and solvents.
Mechanical properties of polyurethane elastomers
Hardness, by shore: 55 90 ShA
Modulus of elasticity 10 %: 0.5 6 MPa
Modulus of elasticity 100 %: 1.6 26 MPa
Modulus of elasticity 300 %: 2.4 35 MPa
Tensile strength: 13 52 MPa
Elongation at break: 250 600 %
Tear strength: 80 300 kN/m
Resilience: 20 65 %
Abrasion resistance: 20 130 mm3
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PU properties [homepage on the Internet]. 2014 [cited 20014 June 20]. Available from: http://www.purelast.com.ua/about_polyurethanes/mechanical_properties.html

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Process

POLYURETHANE PRODUCTION

polyurethane is produced by reaction with a diisocyanate (TDI)and the simplest diol, ethane-1,2diol, a condensation polymerization occurs:

Note

PU production process [homepage on the Internet]. [cited 2014 June 20].


Available from: http://www.essentialchemicalindustry.org/polymers/polyurethane.html/

Traditional amine catalysts have been tertiary amines such as triethylenediamine (TEDA,
1,4-diazabicyclo[2.2.2]octane or DABCO), dimethylcyclohexylamine (DMCHA), and
dimethylethanolamine (DMEA).
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POLYURETHANE APPLICATIONS
Polyurethane formulations cover an extremely wide range of stiffness,
hardness, and densities. Over three quarters of the global consumption of
polyurethane products is in the form of foams, with flexible and rigid types
being roughly equal in market size.

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TRINITROTOLUENE

Specifications
Production
Applications

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TRINITROTOLUENE SPECIFICATIONS
IUPAC name: 2-Methyl-1,3,5-trinitrobenzene
Other names: 2,4,6-Trinitrotoluene,TNT, Trilite, Tolite,
Trinol, Trotyl, Tritolo, Tritolol, Triton, Tritone, Trotol,
Trinitrotoluol, 2,4,6-Trinitromethylbenzene

Properties
Molecular formula: C7H5N3O6
Molar mass: 227.13 g/mol
Appearance: colorless to pale yellow, liquid
Density: 1.654 g/mL, liquid
Melting point: 353.50 K
Boling point: 513 K
Solubility in water: 0.00013 g/cm3 (293.15 K)

Hazards
Main hazard: TNT is poisonous, and skin contact
can cause skin irritation, causing the skin to turn a
bright yellow-orange color
Flash point: 440.15 K

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TRINITROTOLUENE PRODUCTION

TNT production process [homepage on the Internet]. cited 2014 June 20]. Available from:
http://http://http://www.atsdr.cdc.gov/HAC/pha/pha.asp?docid=1378&pg=5

TNT production reaction[homepage on the Internet]. [cited 2014 June 20]. Available from:
http://http://lem.ch.unito.it/didattica/infochimica/2008_Esplosivi/TNT.html

Process
-

First, toluene is nitrated with a mixture of sulfuric and nitric acid to produce
mononitrotoluene (MNT).
The MNT is separated and then renitrated to dinitrotoluene or DNT.
the DNT is nitrated to trinitrotoluene or TNT using an anhydrous mixture of nitric acid and
oleum.

Note
-

Control of nitrogen oxides in feed nitric acid is very important because free nitrogen dioxide
can result in oxidation of the methyl group of toluene. This reaction is highly exothermic and
carries with it the risk of a runaway reaction leading to an explosion.
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TRINITROTOLUENE APPLICATION
TNT is one of the most commonly used explosives for military and industrial applications. It is
valued partly because of its insensitivity to shock and friction, which reduces the risk of
accidental detonation, compared to other more sensitive high explosives such as nitroglycerin.
TNT melts at 80 C (176 F), far below the temperature at which it will spontaneously detonate,
allowing it to be poured as well as safely combined with other explosives. TNT neither absorbs
nor dissolves in water, which allows it to be used effectively in wet environments. Additionally, it
is stable compared to other high explosives.

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BENZOIC ACID

Specifications
Production
Applications

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BENZOIC ACID SPECIFICATIONS


IUPAC name: Benzoic acid
Other names: Carboxybenzene, E210, Dracylic acid,
Phenylmethanoic acid, Benzenecarboxylic acid

Properties
Molecular formula: C7H6O2
Molar mass: 122.12 g/mol
Appearance: Colorless crystalline solid
Density: 1.2659 g/mL(293.15 K)
Viscosity: 1.26 mPa (403.15 K)
Vapor pressure: 0.16 Pa (298.15 K)
Melting point: 395.56 K
Boling point: 522.3 K
Solubility in water: 0.00344 g/cm3 (298.15 K)
Acidity: 4.202 pKa

Thermochemistry
Specific heat capacity: 146.7 J/mol.K
STD molar entropy: 167.6 J/mol.K
STD entropy of formation: 385.2 kJ/mol
STD entropy of combustion: 3228 kJ/mol

Hazards
Main hazard: Irritant
Flash point: 394.65 K
Auto-Ignition temperature: 844.15 K
LD50 : 1700 mg/kg

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BENZOIC ACID PRODUCTION

Process
Benzoic acid is produced commercially by partial oxidation of toluene with oxygen. The
process is catalyzed by cobalt or manganese naphthenates. The process uses cheap raw
materials, and proceeds in high yield.
Note
The advantage of the oxidation of methylbenzene is that it produces no propanone coproduct and also very few impurities. It has a high theoretical atom economy, a high yield,
and produced far less waste than the cumene oxidation process.
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BENZOIC ACID APPLICATIONS


Benzoic acid is mainly consumed in the production of phenol by oxidative decarboxylation at
573.15 673.15 K .
C6H5CO2H + 1/2 O2 C6H5OH + CO2
Medicinal
Benzoic acid is a constituent of Whitfield's ointment which is used for the treatment of fungal skin
diseases such as tinea, ringworm, and athlete's foot.

Food preservation
benzoic acid is used regularly in food preservation, the treatment of bacterial infections, and
combined with other chemicals to create products like repellants and perfumes.
Benzoyl chloride
Benzoic acid is a precursor to benzoyl chloride, C6H5C(O)Cl by treatment with thionyl chloride,
phosgene or one of the chlorides of phosphorus. is an important starting material for several
benzoic acid derivate like benzyl benzoate, which is used in artificial flavors and insect repellents.

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