The document discusses the history, chemistry, applications, production technologies, and manufacturers of cyclohexane. Cyclohexane is produced industrially through the hydrogenation of benzene and is used to make nylon and other polymers. The main production technologies are the UOP Hydrar, Bexane, and IFP processes, with China being the largest global producer of cyclohexane.
The document discusses the history, chemistry, applications, production technologies, and manufacturers of cyclohexane. Cyclohexane is produced industrially through the hydrogenation of benzene and is used to make nylon and other polymers. The main production technologies are the UOP Hydrar, Bexane, and IFP processes, with China being the largest global producer of cyclohexane.
The document discusses the history, chemistry, applications, production technologies, and manufacturers of cyclohexane. Cyclohexane is produced industrially through the hydrogenation of benzene and is used to make nylon and other polymers. The main production technologies are the UOP Hydrar, Bexane, and IFP processes, with China being the largest global producer of cyclohexane.
The document discusses the history, chemistry, applications, production technologies, and manufacturers of cyclohexane. Cyclohexane is produced industrially through the hydrogenation of benzene and is used to make nylon and other polymers. The main production technologies are the UOP Hydrar, Bexane, and IFP processes, with China being the largest global producer of cyclohexane.
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Presented by
Jarukit Junjiewchai 57010169
Chaiwat Kositwiwatkun 57010340 Thithawat Techan 57010498 Pattraporn Samaikaew 57010967 Sorasak Madee 57011317 Department of Chemical Engineering, Faculty of Engineering King Mongkut’s Institute of Technology Ladkrabang, Academic Year 2017 1 Outline
Introduction Market Study Production Technology Conclusion
2 The History of Cyclohexane
1859 1923 First purpose-drilled oil well Dougherty and Taylor in Pennsylvania used nickel as a catalyst
1901 1945 Benzene hydrogenation, forming cyclohexane, Du Pont Patented hydrogenation in the presence of metal catalysts has been of benzene to cyclohexane investigations by Sabatier and Senderens
Ref: Aftalion F., A History of the International Chemical Industry, 2001 3
Chemistry of Cyclohexane Properties Chemical Formula C6H12 −1 Molar Mass 84.16 g·mol Appearance Colorless Liquid Odor Sweet, Gasoline-like Density 0.7781 g/mL, Liquid Melting Point 6.47 °C Found naturally in petroleum Boiling Point 80.74 °C
Solubility in Water Immiscible
Hydrogenation of benzene to Solubility Soluble cyclohexane in ether, Alcohol, Acetone Miscible with Olive Oil Vapor Pressure 78 mmHg (20 °C) 4 Applications of Cyclohexane
Adipic Acid Nylon 66 Electrical Parts,
Automotive Parts Cyclohexane
Caprolactam Nylon 6 Clothing, Carpeting,
Mesh, Trawl
Solvents, Additives
Ref: Cyclohexane Market Analysis By Application, 2017 5
Global Cyclohexane Demand by Application The global cyclohexane market size was estimated at 9,192 kilotons in 2016.
Asia Pacific was leading the cyclohexane consumer;
accounted for over 38.3% of the total revenue in 2016.
Other
XX % Adipid acid and caprolactum
Increasing consumption of automotive and textile applications are expected
to be a key factor driving growth. Ref: Cyclohexane (CX): 2018 World Market Outlook and Forecast up to 2027, [online], available at https://mcgroup.co.uk/researches/cyclohexane-cx 6 Manufacturers China is the largest producer and consumer of cyclohexane globally. Manufacturer Capacity (ton/year) Technology Chevron Philips Chemical 820,000 IFP Huntsman 362,500 Mobil Chemical 350,000 IFP CEPSA 180,000 BASF 130,000 A new process (developed by BASF)
9 UOP Hydrar Process Recycle H2 Purge H2 3 Packed Bed Reactors Separator Cyclohexane Benzene in Series
Recycle Cyclohexane
Operating Condition Advantages Disadvantages
Liquid phase • Catalyst sulfur tolerance • Number of reactor T = 200-350 oC (up to 300 ppm) • Hot spot formation due to P = 30 Bar • Long life catalyst stationary catalyst Catalyst: Pt on Li salt • Good temperature control • Expensive catalyst • No attrition due to stationary • Downtime due to shut down catalyst of the reactor for catalyst replenishment
10 Ref: Mcketta J., Cunningham A., Encyclopedia of Chemical Processing and Design Volume 14, Marcel Dekker, 61-82, 1984 Franck H. G., Stadelhofere J. W., Industrial Aromatic Chemistry, Springer-verlag, 191-193, 1949 Bexane Process Recycle H2 Purge H2 Mixer Multitubular Separator HX Cyclohexane Benzene Reactor
Operating Condition Advantages Disadvantages
Vapor phase • Catalyst prevent isomerization • Consume high amount of T = 370 oC and cracking of cyclohexane electrical energy P = 30 Bar • No attrition due to stationary • Downtime due to shut down Catalyst: Proprietary catalyst of the reactor for catalyst noble metal replenishment • Preheating of feed required
11 Ref: Mcketta J., Cunningham A., Encyclopedia of Chemical Processing and Design Volume 14, Marcel Dekker, 61-82, 1984 Franck H. G., Stadelhofere J. W., Industrial Aromatic Chemistry, Springer-verlag, 191-193, 1949 IFP Process Recycle H2 Fuel Gas H2 Main Finishing Separator Cyclohexane Benzene Reactor Reactor
External HX
Operating Condition Advantages Disadvantages
Liquid phase • No feed preheating required • Attrition of mobile catalyst T = 200 oC (isothermal) • Good temperature control • Friction wear of equipment P = 40 Bar (ewer side reactions) due to moving catalyst Catalyst: Nikcel, • Easier catalyst replacement • Lower catalyst life Raney-Nickel (without shutting down) • Cheaper catalyst than Pt • Lower energy costs
12 Ref: Mcketta J., Cunningham A., Encyclopedia of Chemical Processing and Design Volume 14, Marcel Dekker, 61-82, 1984 Franck H. G., Stadelhofere J. W., Industrial Aromatic Chemistry, Springer-verlag, 191-193, 1949 Hazardous Chemicals Hazard Benzene Hydrogen Cyclohexane Main hazards Potential occupational Flammable Flammable carcinogen, flammable Hazard pictograms
NFPA 704
Flash point −11.63 °C Not applicable −20 °C
Autoignition 497.78 °C 560°C 245 °C temp. Explosive 1.2 - 7.8% 4.0 - 75% 1.3% - 8% limits
13 Case Study - Flixborough Disaster Since 1967, Nypro, UK had produced caprolactam from cyclohexane. Reactor was leaking.
Solubility in Water Immiscible 1.6 mg/L Immiscible Soluble Soluble Soluble in alcohol, chloroform, water, alcohol and Solubility in ether, alcohol, ether, carbon disulfide, some other acetone and olive oil acetone and oils common liquids Vapor Pressure 94.8 mmHg (25 °C) Not applicable 78 mmHg (20 °C)
