Ho Chi Minh city University of Technology, VNU–HCM

Faculty of Chemical Engineering

Division of Organic Chemistry

Chemical Technology of
Organic Compounds
Lecturer : Dr. Nguyễn Đăng Khoa
Room 211 B2
Tel: 38647256 ext. 5681
Email: khoand1989@hcmut.edu.vn
Contents

Week 1: Raw materials in Organic Synthesis Industry

Week 2: Some Popular Chemical Processes to produce raw materials

Week 3: Chemical Based on C1, C2, C3

Week 4: Chemical Based on C4, C5, C6

Week 5: Synthesis of popular organic compounds (Seminar)

Week 6: Synthesis of popular organic compounds (Seminar)

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Introduction_ Chemical processes

Crude oil

Gas Naptha Kerosene Diesel Others

C1-C4 C5-C9 (Paraffin) C14-C20 C18-Cxx
C10-C16

Saturated hydrocarbons
(inert chemicals)
Conversion process (3 reasons) 3
Introduction_ Chemical processes

Chemical
processes

Cracking Reforming  Alkylation

 Dealkylation
 Isomerization
 Polymerization

Thermal Catalytic Catalytic Steam

Cracking cracking reforming reforming
Water-gas shift reaction

Fischer-Tropsch 4
reaction
Cracking

Cracking process

Alkenes Alkanes

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Cracking _ Thermal cracking

Thermal cracking: a chemical process in which saturated hydrocarbons are broken

down into smaller molecules, often unsaturated hydrocarbons.

Classification:  Coking
 Viscosity breaking
 Steam cracking

Mechanism: based on formation of free radicals

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Cracking _ Thermal cracking _ Coking

Feed stock:
 Heavy compounds

Reaction:
 Furnace
 Coke drums

Additional process:
 Hydrotreatment

Application of coke:
 Porous materials
 Pigment
 Electrodes
 Heating sources
 Cement

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Cracking _ Thermal cracking _ Viscosity breaking

Feed stock:
 High viscosity fluids

Reaction:
 Furnace
 Reactor
Application of process:
 Transportation

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Cracking _ Thermal cracking _ Steam cracking

Feed stock: Reaction: Products:

 Light alkanes  Reactors  Ethylene
 Other fractions  Propene
 Butylene
 Butadiene
 BTX
 By product ???
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Cracking _ Thermal cracking _ Steam cracking

 Highly endothermic
1. Temperature  Low temp. favor lighter alkanes
(approximately 800°C for ethane)
 High temp. favor naphtha …
(approximately 650°C for naphtha)

4. Feedstocks
Effect of 2. Residence time
conditions
 Design other parameters  To minimize BTX
contain (0.5-1.2s)

3. Steam/Feed
Ratio

 To remove and reduce coke deposition

 To reduce the contain of raw materials
 Ratio about 0.2-1 for ethane
 Ratio about 1-1.2 for heavy fractions 10
Cracking _ Thermal cracking _ Steam cracking

Ethane feedstock Propane feedstock

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Cracking _ Catalytic cracking

Catalytic cracking: a chemical process in which saturated hydrocarbons are

broken down into smaller molecules, often unsaturated hydrocarbons, in the
presence of acid catalysts.
 To decrease the reaction temp.
 To increase the octane value of products
 Higher contain of isomer compounds
 Need to be pretreat before main process

Classification:  Moving-bed unit (Thermofor catalytic cracking - TCC)

 Fluidized bed process (Fluid catalytic cracking – FCC)
 Deep catalytic cracking

Mechanism: based on formation of carbocations

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Cracking _ Catalytic cracking _ Formation of carbocations

H+

NaY-zeolite HY-zeolite

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Cracking _ Catalytic cracking _ Formation of carbocations

Mechanism: based on formation of carbocations

Reaction at Brønsted acids Reaction at Lewis acids

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Cracking _ Catalytic cracking _ Formation of carbocations

Mechanism: based on formation of carbocations

Reaction at Brønsted acids Reaction at Lewis acids

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Cracking _ Catalytic cracking _ TCC

Feed stock:
 Any fractions

Reaction:
 Column

Disadvantages:
 Poisoned by coke

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Cracking _ Catalytic cracking _ FCC

Feed stock:
 Any fractions

Reaction:
 Column

Advantages:
 Continuous

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Cracking _ Catalytic cracking _ Hydrocracking

Hydrocracking: Less olefinic hydrocarbons

Catalysts: Acid catalysts and cobalt, molybdenum, tungsten, vanadium, palladium, or rare
earth elements

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Cracking _ Comparison

Thermal Catalytic

- Required catalysts and regenerators

- No catalysts
- Temp. about 450-550oC
- Temp. about 500-700oC
- Pressure about 20 atm
- Pressure about 70 atm
- Carbocations
- Free radicals
- Pretreatment is highly recommend
- Pretreatment process is recommend
- Low amount of waste coke
- High amount of waste coke
- Focusing on gasoline and high octane
- C2-C3 and low octane compounds
compounds

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Cracking _ Catalytic reforming

Reforming process: applied to rearrange the structure of petroleum molecules

to produce higher-value molecules from simple molecules or other compounds
Classification:  Catalytic reforming
 Steam reforming
Mechanism: Based on formation carbocations
Purpose: To improve the octane number of a naphtha feedstock by changing its chemical
composition. The methods is based on aromatization and isomerization

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Cracking _ Catalytic reforming

Feed stock: Reaction: Products: Notes:

 Naphtha  Aromatization  BTX  Catalyst amount in reactors
 Gasoline  Isomerization  By product ???  Endothermic reactions
 Dehydrogenation
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Cracking _ Steam reforming

Steam reforming (methane reforming): a process to produce synthesis gas

Mechanism: Based on oxidation reaction with Nickle catalysts at 800oC
Purpose: To provide commercial bulk hydrogen, ammoniac, methanol and others

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