Petrochemical Technology (TKK-2130) 16/17 Spring Semester Petrochemical Technology (TKK-2130) Instructor: Rama Oktavian Email: Oktavian.rama2@gmail.com Office Hr.: M.10-15, Tu. 08-12, W. 13-15, Th. 13-15, F. 09-11

Propylene derivatives https://www.chiyoda-corp.com/technology/en/chemistry/propylene.html

Propylene derivatives

Propylene derivatives

Propylene derivatives

Propylene derivatives

Propylene derivatives Propylene oxide

Propylene derivatives Propylene oxide

Propylene derivatives Propylene oxide production process

Propylene derivatives Propylene chlorohydrin process

Propylene derivatives Propylene chlorohydrin process Reaction

Propylene derivatives Propylene chlorohydrin process

Propylene derivatives Propylene oxidation process using peroxide The hydroperoxide process to propylene oxide involves: the basic steps of oxidation of an organic to its hydroperoxide, epoxidation of propylene with the hydroperoxide, purification of the propylene oxide, and conversion of the co-product alcohol to a useful product for sale.

Propylene derivatives Propylene oxidation process using peroxide Main reaction Hydroperoxide reaction

Propylene derivatives Propylene oxidation process using peroxide

Propylene derivatives Propylene glycol

Propylene derivatives Propylene glycol

Propylene derivatives Propylene glycol uses

Propylene derivatives Propylene glycol

Propylene derivatives Isopropanol Source: ICIS

Propylene derivatives Isopropanol Source: ICIS

Propylene derivatives Isopropanol

Propylene derivatives Isopropanol manufacturing process http://nptel.ac.in/courses/103103029/18

Propylene derivatives Acetone Source: IHS

Propylene derivatives Acetone Source: ICIS

Propylene derivatives Acetone manufacturing process

Propylene derivatives Acetone manufacturing process Acetone manufacturing process by dehydrogenation of isopropanol

Propylene derivatives Acetone manufacturing process by dehydrogenation of isopropanol Catalytic dehydrogenation takes place in the liquid phase at l5O"C and atmospheric pressure, in the presence of Raney niekel

Propylene derivatives Acetone manufacturing process by direct oxidation of propanol

Propylene derivatives Acetone manufacturing process by direct oxidation of propanol Overall reaction

Propylene derivatives Propylene oxidation process technology Find the process scheme Explain it in detail

Propylene derivatives Propylene glycol using glycerol Find the process scheme Explain it in detail

Aromatic compound

Aromatic compound

Aromatic compound

Aromatic compound

Aromatic compound

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

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 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

Ethylbenzene production

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 30-100 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 mononitrotoluene 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 P-Xylene production

Aromatic compound Recent update Developing technologies China Petroleum and Chemical Corporation (CPCC) and Sinopec have developed a new composite solvent for extractive distillation (ED) of aromatics. ExxonMobil proposes a bound zeolite catalyst for use in alkylation, transalkylation or isomerization of aromatic hydrocarbons. 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 5-Hydroxymethylfurfural 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

Thank You !