Chapter- 2 Main Petrochemicals
2.1 Introduction to petrochemicals
➢Petrochemicals are chemicals derived from petroleum.
➢ These chemicals include a large number of aliphatic and aromatic organic
compounds of various functional groups.
➢Examples include benzene and its derivatives, methane, ethylene, propylene,
butene, toluene, and xylene and their derivatives.
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2.2. Chemical conversions for manufacture of petrochemicals
➢There are two petrochemical classes
1. Olefins including ethylene and propylene
2. Aromatics including benzene, toluene and xylene isomers.
➢Oil refineries produce olefins and aromatics by fluid catalytic cracking of
petroleum fractions.
➢Chemical plants produce olefins by steam cracking of natural gas liquids
like ethane and propane.
➢Aromatics are produced by catalytic reforming of naphtha. Olefins and
aromatics are the building blocks for a wide range of materials such as
solvents, detergents, and adhesives.
➢Olefins are the basis for polymers and oligomers used in plastics, resins,
fibers, elastomers, lubricants, and gels.
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2.3. Petrochemicals from Ethylene and Propylene,
Ethylene: The major uses for ethylene are in the synthesis of polymers
(polyethylene) and in ethylene dichloride, a precursor to vinyl chloride.
➢Other important products are ethylene oxide (a precursor to ethylene glycol) and
ethylbenzene (a precursor to styrene).
List of chemicals and their function which are produced from ethylene
Ethylene: the simplest olefin; used as a chemical feedstock
✓ Polyethylene : it is a polymerized ethylene
✓ Ethanol : is produced via ethylene hydration (i.e chemical reaction adding water)
✓Ethylene oxide : is produced via ethylene oxidation
✓ Ethylene glycol: is produced via ethylene oxide hydration
✓ Vinyl chloride: it is a monomer for polyvinyl chloride
✓ Polyvinyl chloride (PVC): it is a type of plastic used for piping, tubing, and other
things
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Chemicals produced from propylene
Propylene : used as a monomer and a chemical feedstock
✓ Isopropyl alcohol ( 2-propanol): often used as a solvent or rubbing alcohol
✓Polypropylene : it is polymerized propylene
✓ Polyol : used in the production of polyurethanes
✓Glycol ethers: from condensation of glycols
2. Petrochemicals from benzene(BTX)
Benzene : it is the simplest aromatic hydrocarbon
✓Ethylbenzene : made from benzene and ethylene
✓ Styrene made by dehydrogenation of ethylbenzene and used as a monomer
✓ Polystyrenes: it is a polymers with styrene as a monomer
✓ Phenol (hydroxybenzene): often made by the cumene process
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2.4. Manufacture of Acetylene, Ethylene oxide, Acrylonitile, Dimethyl terephthalate
❑Manufacture of Acetylene
• Acetylene (CH≡CH, melting point –81.5°C, boiling point–84°C) is an extremely reactive
hydrocarbon & moderately soluble in water / alcohol
• There are two Methods of Manufacturing
1. From calcium carbide reaction with water
Reaction: CaC2 + 2H2O → HC≡CH + Ca(OH)2
2. pyrolysis, or cracking, of natural gas or liquid hydrocarbon feeds.
▪ It can be produced from crude oil.
• The processes includes ,partial oxidation using oxygen thermal cracking, supply both the high
temperature & energy.
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• Manufacture of Ethylene oxide
• Ethylene oxide is an organic compound with the formula C2H4O. It is a cyclic ether and
the simplest epoxide: a three-membered ring consisting of one oxygen atom and two
carbon atoms.
• Ethylene oxide is a colorless and flammable gas. Ethylene oxide is isomeric with
acetaldehyde and with vinyl alcohol.
• It (freezing point: –111.7oC, boiling point: 10.4oC) is a colorless gas
• It is miscible in all proportions with water/ alcohol &very soluble in ether.
• Ethylene oxide is industrially produced by oxidation of ethylene in the presence of silver
catalyst.
Reaction:
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❑Manufacture of Acrylonitrile
• Acrylonitrile (2-propenonitrile, propene nitrile, vinyl cyanide, CH2=CHCN; freezing point: –
83.5oC, boiling point: 77.3oC)
• It is manufactured from acetylene by reaction with hydrogen cyanide.
Reaction :HC≡CH + HCN → CH2=CHCN
• presently the ammoxidation (ammonoxidation or oxyamination) of propylene that involves
reaction of propylene, ammonia, and oxygen at 400 to 450oC & (48 to 200 kPa) in the
presence of catalyst
Reaction :2CH2=CHCH3 + 2NH3 + 3O2 → 2CH2=CHCN + 6H2O
Manufacture of dimethyl terephthalate
• Dimethyl terephthalate has melting point of 141oC
• It is prepared by oxidation of p-xylene & subsequent esterification with methyl alcohol
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Chapter- 3
Basic Organic Products
3.1 Introduction to Industrial organic synthesis
❖Most of industrial organic chemicals are derived from petroleum (oil) and natural
gas.
❖Historically, most organic chemicals had been obtained as by- products from the
coking of coal.
Manufacture of Methanol
❖Methanol (methyl alcohol, CH3OH), an important solvent and precursor for many
organic chemicals, is made by a process developed in the 1920s
CO + 2 H2 → CH3OH
❖A major use of methanol is the production of acetic acid via carbonylation.
CH3OH + CO → CH3CO2H
❖Acetic acid (ethanoic acid, CH3CO2H) was for many years made by the simple
oxidation of ethanol, but the carbonylation of methanol has now largely displaced
this process.
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Manufacture of Acetaldehyde
❖ Acetaldehyde, CH3CHO is an important intermediate in industrial organic synthesis.
❖ Acetic acid, acetic anhydride, n-butanol, and 2-ethylhexanol are the major products derived
from acetaldehyde.
❖ Acetaldehyde (ethanal) was first prepared by Scheele in 1774, by the action of manganese
dioxide and sulfuric acid on ethanol.
❖ Commercial processes for the production of acetaldehyde include:
✓ the oxidation or dehydrogenation of ethanol,
✓ the addition of water to acetylene, partial oxidation of hydrocarbons,
✓ and the direct oxidation of ethylene.
Use
❖ Acetaldehyde is a normal intermediate product in the respiration of higher plants, alcoholic
fermentation, in the decomposition of sugars in the body and, hence, occurs in traces in blood.
❖ It occurs in traces in all matured fruits that have a bitter taste before developing;
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Manufacture of Acetic acid
Properties
❖Acetic acid is also known as ethanoic acid, ethylic acid, vinegar acid, and methane
carboxylic acid
❖ it has the chemical formula of CH3COOH (molecular weight of 60.05).
❖It is a colorless liquid with a pungent smell.
❖The boiling point of acetic acid is 118°C and the melting point of its crystals is 16.6°C.
❖Acetic acid is soluble in alcohol, miscible with water, glycerol
Production and uses
❖Commercial production of acetic acid is often accomplished by a chemical
reaction of methanol and carbon monoxide (with catalyst).
❖Other production methods include:
✓ liquid- and vapor-phase oxidation of petroleum gases (with catalyst),
✓oxidation of acetaldehyde, and
✓fermentative oxidation of ethanol.
❖The major use for Acetic Acid is as a raw material for vinyl acetate, either by
reaction with ethylene and oxygen or with acetylene.
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Manufacture of Acetone
❖Acetone is the organic compound with the formula OC(CH3)2.
❖This colorless, mobile, flammable liquid is the simplest example of the ketones.
❖due to the fact that acetone is miscible with water, and virtually all organic solvents, it serves as an
important solvent in its own right, typically the solvent of choice for cleaning purposes in the
laboratory.
❖Familiar household uses of acetone are as the active ingredient in nail polish remover and as paint
thinner and sanitary cleaner or nail polish remover base.
❖ It is a common building block in organic chemistry.
❖ In addition to being manufactured, acetone also occurs naturally, even being biosynthesized in
small amounts in the human body.
❖ Acetone is produced by the catalytic dehydration of iso-propyl alcohol.
• It can be produced directly or indirectly from propene. Most commonly, in the cumene process,
benzene is alkylated with propene and the resulting cumene (isopropylbenzene) is oxidized to give
phenol and acetone:
C6H5CH(CH3)2 + O2 → C6H5OH + OC(CH3)2
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Phenol and Styrene
❖Phenol and acetone each have a number of important commercial uses, but they
also have an important use together.
❖ Phenol and acetone can be condensed to form bisphenol A, which is used in the
production of poly-carbonate and epoxy resins.
❖Styrene (phenylethylene or vinyl benzene, C6H5−CH=CH2) is made from
ethylene by reaction with benzene to form ethylbenzene, followed by
dehydrogenation.
❖Most benzene is alkylated with ethylene to form ethylbenzene, which is
dehydrogenated to styrene.
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End of Chapter-3
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