Chemical properties Properties of

Alkanes
Called paraffins (low affinity compounds) because
they do not react as most chemicals
They will burn in a flame, producing carbon dioxide,
water, and heat
They react with Cl2 in the presence of light to replace
Hs with Cls (not controlled)
They can cracked under high temperature and
pressurre
Reactions of Alkanes

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 Reactions of Alkanes

Combustion
Free radical Halogenation
Cracking
Free radical cracking (Pirolisis)
Catalitic cracking (cationic)
Isomerisasi
Combustion
Burning of hydrocarbons in the presence of
oxygen (high temperature oxidation of
hydrocarbon fuels) yields a large amount of
energy as heat and products which are stable
oxides
CH4 + 2O2 CO2 + 2H2O
(bond energies energy release ~810 kJ)

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Heats of Combustion Alkane + O2 CO2 + H2O

166.6 164.0
158.7 158.3 158.6
157.4 157.4

Long-chain =>
 Cycloalkane Stability

5- and 6-membered rings most stable

Bond angle closest to 109.5
Angle (Baeyer) strain
Measured by heats of combustion
per -CH2 -
=>
 FREE RADICAL HALOGENATION

Example: methane + chlorine

H Cl
h
H C Cl2 H C HCl
H H
H H

multistep process involving radicals

Halogenation = Substitution

CH4 + Cl2 CH3Cl + HCl

 Free Radicals

very reactive species

with an odd (unpaired) H
electron (a total of only H C
7 electrons) H
sp2 hybridised
trigonal planar
 ALKANES - HALOGENATION

Mechanism involves three stages

Step 1. Initiation
the initial production of free radicals

h
Cl Cl Cl Cl
reactive
species
 Step 2. Propagation
radicals undergo substitution reactions
chain reaction

H3C H Cl H3C + H Cl

H3C Cl Cl H3C Cl + Cl
 Step 3. Termination
radicals collide and form stable products
destruction / removal of free radicals
chain reaction is broken

Cl Cl Cl Cl

H3C CH3 H3C CH3

H3C Cl H3C Cl
Cracking= Pyrolysis

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 Cracking

Catalyst + heat
large molecule smaller molecules

Cracking is the name given to the process by which large hydrocarbon

molecules are broken into shorter chains or monomers. This is done
under high pressures and temperatures, but a catalyst allows slightly
lower pressures and temperatures to be used.
 Cracking

An example of possible fractions naphtha might split into

is shown below.

Once separated the hydrocarbons are filtered to purify them.

http://www.doitpoms.ac.uk/tlplib/recycling-polymers/origin.php
Cracking In Petroleum industry
C(m+n)H2(m+n)+2 CmH2m + CnH2n+2
alkane alkene alkane
(kerosene (gasoline size)
gas/oil size)

The industrially used catalysts are zeolites (finely-porous

aluminosilicates), which are mixed with the naphtha (gasoline range)
as a fine powder. This is blown through a chamber at 500C.

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 Cracking In Petroleum industry

The introduction of catalytic cracking and polymerization

processes in the mid- to late 1930's met the demand by providing
improved gasoline yields and higher octane numbers.

. Higher-compression gasoline engines required higher-

octane gasoline with better antiknock characteristics.

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Cracking In Petroleum industry
 Catalytic - uses a catalyst to speed up the cracking
reaction. Catalysts include zeolite, aluminum hydrosilicate,
bauxite and silica-alumina.

fluid catalytic cracking - a hot, fluid catalyst (1000

degrees Fahrenheit / 538 degrees Celsius) cracks heavy
gas oil into diesel oils and gasoline.

hydrocracking - similar to fluid catalytic cracking, but

uses a different catalyst, lower temperatures, higher
pressure, and hydrogen gas. It takes heavy oil and
cracks it into gasoline and kerosene (jet fuel).

http://science.howstuffworks.com/oil-refining5.htm
20
Example mechanism
Radical cracking

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Example mechanism OF catalitic
cracking

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Isomerization

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