13/14 Spring Semester
Petrochemical Technology
(TKK-2130)
Instructor: Rama Oktavian
Email: rama.oktavian86@gmail.com
Office Hr.: M.13-15, Tu. 13-15, W. 13-15, Th. 13-15, F. 09-11
Aromatic compound
Aromatic compound
Benzene
a cyclical, six carbon, six hydrogen molecule
a clear, colourless, volatile liquid with a characteristic ‘aromatic’ smell
Aromatic compound
Benzene
http://www.epa.gov/otaq/regs/toxics/airtox1b.pdf
Aromatic compound
Benzene uses
combined and processed with other basic chemicals (such as ethylene or
propylene) to produce countless consumer goods
The largest derivative outlet for benzene is ethylbenzene
production of styrene
polystyrene
widely used to produce cumene
Phenol, cyclohexane, and aniline
http://www.shell.com/global/products-services/solutions-for-businesses/chemicals/products/aromatics/benzene.html
Aromatic compound
Benzene uses
Aromatic compound
Benzene global demand
http://mcgroup.co.uk/researches/benzene
Aromatic compound
Benzene uses
http://www.shell.com/global/products-services/solutions-for-businesses/chemicals/products/aromatics/benzene.html
Aromatic compound
Benzene uses
http://mcgroup.co.uk/uc/2013/05/Global-Styrene-Consumption-by-End-Use-Sector-in-2013.jpg
Aromatic compound
Benzene global demand
According to a new IHS Chemical (NYSE: IHS) global market study,
global demand for benzene, an aromatic hydrocarbon and one of the
primary chemical building blocks for the petrochemical industry,
increased to 43.7 million metric tons in 2013, an increase of 2.8
percent above demand for benzene in 2012.
http://press.ihs.com/press-release/aromatic-chemicals/global-demand-benzene-primary-chemical-building-block-chemical-indu
Aromatic compound
Benzene demands
http://www.shell.com/global/products-services/solutions-for-businesses/chemicals/products/aromatics/benzene.html
Aromatic compound
Benzene sources
http://www.chemsystems.com/images/PERP0607_6_BenzeneToluene/0607_6_Fig1.JPG
Aromatic compound
Benzene sources
http://www.2b1stconsulting.com/wp-content/uploads/2012/07/Aromatics-definition.jpg
Aromatic compound
Benzene production
Extractive distillation
Catalytic reforming
Toluene hydrodealkylation and disproportionation
Pyrolysis gasoline
Production from coal tar
Benzene production
Extractive distillation
http://www.2b1stconsulting.com/wp-content/uploads/2012/07/Aromatics-definition.jpg
Benzene production
Extractive distillation
Sulfolane Extractive Distillation Technology (SED)
http://english.sinopec.com/products_service/License/Petrochemical/20090908/7573.shtml
Benzene production
Catalytic reforming
Reforming takes straight chain hydrocarbons in the C6 to C8 range from the
gasoline or naphtha fractions and rearranges them into compounds containing
benzene rings
A typical catalyst is a mixture of platinum and aluminium oxide
Benzene production
Production from pyrolysis gasoline
Pyrolysis gasoline is the by-product of steam cracking of paraffin gases,
naphtha, gas oils and other hydrocarbons used to make ethylene.
It contains 60% aromatics, 50% of which is benzene
http://www.dow.com/hydrocarbons/aromatics/company/production.htm
Aromatic compound
Toluene = methylbenzene
http://www.sigmaaldrich.com/chemistry/solvents/toluene-center/physical-properties.html
Aromatic compound
Toluene uses
Aromatic compound
Toluene uses
Aromatic compound
TDI uses
As raw material for flexible polyurethane (PU) foam used in furniture, mattresses
and car seats.
rigid foams and adhesives, paints, concrete sealers, as a cross-linking agent for
nylon 6, and as an intermediate in PU coatings and elastomers
http://www.icis.com/resources/news/2008/01/21/9093901/chemical-profile-tdi/
Toluene
Toluene consumption
http://mcgroup.co.uk/uc/2013/05/Toluene-2014-World-Market-Outlook-and-Forecast-up-to-2018.jpg
Toluene
Toluene consumption
http://mcgroup.co.uk/uc/2013/05/Toluene-Diisocyanate-TDI-2014-World-Market-Outlook-and-Forecast-up-to-2018.jpg
Toluene
Toluene production technology
Toluene
Toluene production technology
Toluene
Toluene to benzene production technology
Toluene hydrodealkylation
The hydrodealkylation is conducted either purely thermally at 550-800°C and 30100 bar or catalytically at somewhat lower temperatures of 500-650 °C and 30-50
bar Over Cr2O3, Mo2O3, or CoO on supports (e.g., Al2O3) or, as in a recent
development, at 400-480°C over Rh/Al2O3.
Toluene
Toluene to benzene production technology
Toluene disproportionation
2 toluene molecules are reacted and the methyl groups rearranged from one
toluene molecule to the other, yielding one benzene molecule and one xylene
molecule
Toluene
Toluene to TDI production process
Toluene diisocyanate (TDI) is currently produced via a three-step process:
- Nitration of toluene to dinitrotoluene (DNT)
Toluene is nitrated in two steps, producing the three isomers of mononitrotoluene.
and the mixed mononitrobenzene isomers are further nitrated resulting in
dinitrotoluene isomers
- Reduction of dinitrotoluene to toluene diamine (TDA)
Dinitrotoluene is dissolved in methanol and reduced continuously by reaction with
hydrogen in the presence of a suitable catalyst
http://www.chemsystems.com/about/cs/news/items/PERP%200708S9_TDI.cfm
Toluene
Toluene to TDI production process
Toluene diisocyanate (TDI) is currently produced via a three-step process:
- Phosgenation of TDA to TDI
The 80/20 TDA produced by any of the above processes is converted to
diisocyanate by reaction with phosgene
phosgene
http://www.chemsystems.com/about/cs/news/items/PERP%200708S9_TDI.cfm
Aromatic compound
Xylene
the o- isomer has the IUPAC name of 1,2-dimethylbenzene
the m- isomer has the IUPAC name of 1,3-dimethylbenzene
the p- isomer has the IUPAC name of 1,4-dimethylbenzene
Aromatic compound
Xylene
Properties
The melting point ranges from −47.87 °C (−54.17 °F) (m-xylene) to 13.26 °C
(55.87 °F) (p-xylene)
The boiling point for each isomer is around 140 °C (284.00 °F)
The density of each is around 0.87 g/mL (7.26 lb/U.S. gallon)
Xylene in air can be smelled at 0.08 to 3.7 parts of xylene per million parts of air
(ppm)
https://www.princeton.edu/~achaney/tmve/wiki100k/docs/Xylene.html
Aromatic compound
Xylene uses
Aromatic compound
Recent update
Developing technologies
1. China Petroleum and Chemical Corporation (CPCC) and Sinopec have
developed a new composite solvent for extractive distillation (ED) of aromatics.
2. ExxonMobil proposes a bound zeolite catalyst for use in alkylation,
transalkylation or isomerization of aromatic hydrocarbons.
3. UOP has developed a new family of zeolites that can be used in alkylation of
aromatics, transalkylation of aromatics, isomerization of aromatics and alkylation
of isoparaffins.
Aromatic compound
Recent update
Catalyst development in aromatic hydrocarbon production using catalytic
pyrolysis
1. Aromatic hydrocarbons production from ex situ catalysis of pyrolysis vapor over
Zinc modified ZSM-5 in a packed-bed catalysis coupled with microwave pyrolysis
reactor, published in Fuel Volume 129, 1 August 2014, Pages 78–85
Aromatic compound
Recent update
Catalyst development in aromatic hydrocarbon production using catalytic
pyrolysis from biomass
1. Production of aromatic hydrocarbons by catalytic pyrolysis of microalgae with
zeolites: Catalyst screening in a pyroprobe, published in Bioresource Technology
Volume 139, July 2013, Pages 397–401
Aromatic compound
Recent update
Catalyst development in aromatic hydrocarbon production using catalytic
pyrolysis from biomass
2. Production of aromatic hydrocarbons through catalytic pyrolysis of 5Hydroxymethylfurfural from biomass, published in Bioresource Technology Volume
147, November 2013, Pages 37–42
Aromatic compound
Recent update
Catalyst development in aromatic hydrocarbon production using catalytic
pyrolysis from biomass
3. Production of Light Aromatic Hydrocarbons from Biomass by Catalytic Pyrolysis,
published in Chinese Journal of Catalysis Volume Volume 29, Issue 9, September
2008, Pages 907–912