Professional Documents
Culture Documents
3 Chapter Three Hydrocarbons and Classifications
3 Chapter Three Hydrocarbons and Classifications
3 Chapter Three Hydrocarbons and Classifications
2020 - 2021
2
2
1
CHE428
3
3
Hydrocarbons
Types of Hydrocarbons
Refining Process of Petroleum
Fractional distillation
Petroleum-based Liquid Fuels
Non-petroleum-based Liquid Fuels
Gaseous Fuels
Fuel Characteristics
Usage of Hydrocarbons
4
4
2
What is it? Formation General
Introduction
HYDROCARBONS
Burning
Or Combustion Classification
Or Types
Usages
5
5
6
6
3
Hydrocarbons are referred to as consisting of a
"backbone" or "skeleton" composed entirely of carbon and
hydrogen and other bonded compounds, and lack a functional
group that generally facilitates combustion.
7
7
TYPES
OF
HYDROCARBONS
8
8
4
The classifications for hydrocarbons defined by
IUPAC (International Union of Pure and Applied
Chemistry) nomenclature of organic chemistry are as
follows:
HYDROCARBONS
Saturated
Unsaturated Aromatic
hydrocarbons Cycloalkanes
hydrocarbons hydrocarbons
(alkanes)
9
9
HYDROCARBONS
2 Unsaturated hydrocarbons
3 Cycloalkanes
4 Aromatic hydrocarbons
10
10
5
1-Saturated hydrocarbons (alkanes) are the most
simple of the hydrocarbon species and are composed entirely of
single bonds and are saturated with hydrogen.
n-Butane
C4H10 Isobutane
CH3CH2CH2CH3 (CH3)3CH
bp -0.4°C bp -10.2°C
12
12
6
C5H12
CH3CH2CH2CH2CH3 (CH3)2CHCH2CH3
n-Pentane Isopentane
(CH3)4C
Neopentane
13
13
14
14
7
H CH2CH3 H3C H
C C C C
H H H3C H
1-Butene 2-Methylpropene
C C C C
H H H CH3
cis-2-Butene trans-2-Butene
15
15
1 Meth
2 Eth
3 Prop
Straight-chain alkanes take the
4 But
5 Pent suffix "-ane" and are prefixed
6 Hex depending on the number of carbon
7 Hept atoms in the chain.
8 Oct The first few are:
9 Non
10 Dec
11 Undec
12 Dodec
13 Tridec
14 Tetradec
15 Pentadec
20 Eicos
30 Triacont
16
16
8
17
17
9
3-Cycloalkanes are hydrocarbons containing one or
more carbon rings to which hydrogen atoms are
attached.
19
19
10
Hydrogen has one electron in its outer orbit.
That means it tends to combine with other elements so that
it will fill its outer orbit with two electrons.
It would need four more to fill the orbit with the maximum
of 8 electrons.
11
One form of chemical bonding is when two atoms share a
single electron.
In the example above, Hydrogen now has a full outer orbit, while
Carbon still is 3 short of filling its outer orbit.
In reality, the outer orbit of Carbon is much bigger than the outer
orbit of Hydrogen. They are drawn the same size for the sake of
convenience.
If we continue to add Hydrogen atoms, we can fill Carbon's outer
orbit too.
Methane
(CH4)
The outer orbits of both Hydrogen and Carbon are filled in the
resulting compound Methane, which is a volatile gas.
24
24
12
Now, two Carbon atoms can also share electrons.
Ethane (C2H6)
H H
H
H
H H
26
26
13
Ethane
(C2H6)
Ethane
(C2H6)
14
can be:
Pentane Cyclopentane
Pentadiene
5 Isopentane Pentene Pentyne Methylcyclobutane
Isoprene
Neopentane Ethylcyclopropane
Cyclohexane
Methylcyclopentane
6 Hexane Hexene Hexyne Hexadiene
Ethylcyclobutane
Propylcyclopropane
Cycloheptane
7 Heptane Heptene Heptyne Heptadiene
Methylcyclohexane
8 Octane Octene Octyne Cyclooctane Octadiene
9 Nonane Nonene Nonyne Cyclononane Nonadiene
10 Decane Decene Decyne Cyclodecane Decadiene
30
15
Cyclobutane
Butane
4 Isobutane
Butene Butyne Methylcyclopropa Butadiene
ne
Pentane Cyclopentane
Pentadiene
5 Isopentane Pentene Pentyne Methylcyclobutane
Isoprene
Neopentane Ethylcyclopropane
Cyclohexane
Methylcyclopentan
e
6 Hexane Hexene Hexyne
Ethylcyclobutane
Hexadiene
Propylcyclopropan
e
Cycloheptane
7 Heptane Heptene Heptyne
Methylcyclohexane
Heptadiene
31
31
Number of
carbon Alkane Alkene Alkyne Cycloalkane Alkadiene
atoms
1 Methane — — — —
32
32
16
Example
If
Number of
Carbon Atoms = 3
33
33
3D
IUPAC name
C3H8 (International Union of Pure and
Applied Chemistry) 34
34
17
C3H? Propane CnH2n+2 1-ALKANE
Propane is a three-carbon alkane, normally a gas, but
compressible to a transportable liquid. It is derived from
other petroleum products during oil or natural gas
processing.
3D
IUPAC name
C3H8
35
35
IUPAC name
18
C3H? Propene CnH2n 2-ALKENE
Propene, also known as propylene, is an unsaturated organic
compound having the chemical formula C3H6.
IUPAC name
C3H6 37
37
CH3C≡CH
3D
IUPAC name
C3H4 (International Union of Pure and
Applied Chemistry) 38
38
19
C3H? Propyne CnH2n-2 3-ALKYNE
Alkynes are hydrocarbons that have
a triple bond between two carbon atoms, with the formula
CnH2n-2. Alkynes are traditionally known as acetylenes.
Methylacetylene (propyne) is an alkyne with the chemical
formula CH3C≡CH.
CH3C≡CH
3D
IUPAC name
C3H4 39
39
CnH2n
3D
20
C3H? Cyclopropane 4-Cycloalkane
Cyclopropane is a cycloalkane molecule with the molecular
formula C3H6, consisting of three carbon atoms linked to
each other to form a ring, with each carbon atom bearing
two hydrogen atoms.
CnH2n
3D
IUPAC name 42
42
21
C3H? Allene CnH2n-2 5-Allene
An allene is a hydrocarbon in which one atom of carbon is
connected by double bonds with two other atoms of
carbon.
Allene also is the common name for the parent compound
of this series, propadiene.
3D
C3H4
43
43
44
44
22
3-ALKYNE CnH2n-2 C3H4
45
45
46
46
23
cyclohexane
phenylbenzene
ethylbenzene
1-ethyl-3-propylbenzene
propylbenzene
2-phenylpropane
47
47
Structure of benzene
48
48
24
Formula Prefix Suffix Name Structure
H
49
49
This fact is used in the refining process to separate crude oil into
more desirable products by fractional distillation.
50
50
25
Fractional distillation:
The distillation of petroleum is carried out
in a tubular furnace with a tall steel
fractionating column. The crude oil is
pumped continuously through a heated
pipe and flashed into the fractionating
column.
The vapours of the oil as they rise up the
fractionating column become cooler and
condensate on the shelves at various
heights.
The heavier compounds have a high boiling point and, as the
vapours rise in the tower and are cooled, the heavy fractions
precipitate first and are removed from the tower.
The light hydrocarbons rise to the top of the column before
condensing, while the compounds with intermediate boiling points
are removed at the intermediate stages. 51
51
Outlets are provided in the side of the column at suitable heights for
withdrawal of several fractions.
26
After distillation, a residue of paraffin wax or asphalt is left,
depending on the base of the oil, i.e. whether it is paraffin or
naphthene.
The demand ratio of certain
components, such as gasoline to
other petroleum components, far
exceeds the naturally occurring
ratio of gasoline found in crude
oil.
This has led to the development
of refinery processes to ‘crack’
the larger molecules into smaller
molecules and ‘polymerize’ or
‘alkylate’ small molecules into
larger molecules to get the boiling
points of the resulting component
in the gasoline range. 53
53
Cracking:
It is the process of breaking down the large and complex molecules
into lighter and simpler compounds.
Cracking reactions may be thermal or catalytic.
In thermal cracking the heavy hydrocarbons are subjected to high
temperature and pressure.
At high temperature, the kinetic energy of the molecules increases
and as a result they move faster and strike harder.
Thus, some of the chemical bonds holding the carbon atoms together
break away and the molecules split into lighter and smaller
compounds.
In catalytic cracking, somewhat lower pressure and temperature are
required and the smaller molecules are found to be isomeric rather
than normal hydrocarbons.
This is desirable because the isomeric compounds have better
antiknock characteristics. 54
54
27
An example of a cracking reaction is the breaking off the chain-line
structure of paraffin, n-tetradecane into two smaller constituents,
one being a paraffin, C7H16, and the other an olefin, C7H14, i.e.
C14 H 30 C7 H16 C7 H 14
55
55
Hydrogenation:
It may be described as a cracking process which occurs in an
atmospheric of hydrogen.
28
Absorption:
The gases leaving the refining processes may contain some heavier
hydrocarbons in the vapour state, which may fall into the gasoline
range.
In this process the gases come into contact with a kerosene or light
oil which absorbs the heavy hydrocarbon vapours.
The vapours are then driven out from the oil by heating.
Polymerization:
It is the process of combining the unsaturated products of one family
(two or more olefinic molecules) to form heavier and stable
compounds that have a high antiknock rating.
58
58
29
Alkylation:
It is the process of combining light undesirable hydrocarbons of one
chemical family with another family to form a larger molecule.
Isomerization:
It is the process of changing the relative position of atoms within the
molecule of a hydrocarbon without changing its molecular formula.
59
59
Cyclization:
It is a process of joining together the ends of a straight chain
molecule to form a ring compound of the naphthene family.
Aromatization:
Reforming:
It is used to convert low antiknock quality gasoline into high
antiknock quality.
It does not increase the total gasoline volume as in polymerization
and alkylation. 60
60
30
Finished blended products:
These liquid products are then put through the various finishing
processes to reduce the sulphur and wax contents.
61
61
31
Kerosene:
It is the next fraction heavier than gasoline.
It is widely used in lamps, heaters, stoves, and similar appliances.
It may also be used in CI engines and gas turbines.
The specific gravity of kerosene lies between 0.78 and 0.85.
Diesel oils:
There are petroleum fractions heavier than kerosene.
These oils cover a wide range of specific gravity and a very wide
distillation range.
Their composition is controlled to make them suitable for use in
various types of CI engines.
The heating value of a typical diesel oil is 42,000 kJ/kg.
63
63
Fuel oils:
The range of specific gravity and the distillation range are similar to
those of diesel oil.
Their composition does not require accurate control as is required in
the case of diesel oils.
These fuel are used in continuous burners.
Lubricating oils:
64
64
32
Non-petroleum-based Liquid Fuels:
Benzol
Alcohol
Acetone
Diethyl-ether
65
65
Gaseous Fuels:
Gaseous fuels present no difficulty regarding mixing with air,
distributing homogeneous mixture to various cylinders and cold
starting.
However, gaseous fuels create problems of storage and handling
large volumes especially in automobiles.
66
66
33
Natural Gas:
Natural gas is a mixture of several different gases.
The primary constituent is methane, which typically makes up 85-
99% of the total volume.
The other constituents include other hydrocarbons, inert gases such
as nitrogen, helium and carbon dioxide, and traces of hydrogen
sulphide and water.
The non-methane hydrocarbons present in natural gas consist
primarily of ethane.
The remainder is made up mostly of propane and butane, with some
traces of C5 and higher species.
Natural gas is an excellent fuel for SI engines.
As a gas under normal conditions, it mixes readily with air in any
proportion.
67
67
34
Liquefied Petroleum Gas (LPG):
Liquefied petroleum gas (LPG) is a product of petroleum gases,
principally propane (C3H8), propylene (C3H6) and butane (C4H10).
Liquefied petroleum gases are used as fuels for stoves, trucks, buses,
and tractors in many parts of the world.
69
69
Since propane and butane are heavier than air, the escaping gas will
tend to settle and collect in pockets thus creating an explosion
hazard.
The LPG is suitable for IC engines because of its availability and low
carbon content, thus resulting in drastic reduction in exhaust
emissions.
Engines with natural gas and LPG can run lean because of their
better distribution and higher misfire limits.
70
70
35
Producer Gas:
It is made by burning carbonaceous (coal, wood, charcoal, coke etc.)
with a large deficiency of air and treating with steam.
The products of this partial combustion contain CO and H2 in
sufficient quantities, so that they can be used in an engine as a fuel.
The producer gas has a high percentage of N2, since air is used.
Coal Gas:
Coal is heated to temperatures up to 1500 °C in the presence of very
little air.
Hydrogen:
With the imposition of stringent emission standards along with the
decreasing availability of petroleum products, it is imperative that a
search for low polluting alternative fuels be made.
36
Hydrogen has emerged as a potential fuel for internal combustion
engines.
It is generally considered to be non-polluting because hydrogen
contains no carbon.
Species such as carbon monoxide and unburned hydrocarbons,
which are normally found in gasoline fuelled engines, would be
virtually eliminated in the exhaust.
Hydrogen is found in abundant quantities in various forms and can
be considered to be an almost inexhaustible fuel.
It can be adapted as a fuel to engines without major design changes.
The problems generally experienced in a hydrogen-fueled engine are
the backfiring, preignition, knocking and rapid rate of pressure rise
during the combustion process because of the higher flame speed.
Backfiring is mainly due to less ignition energy for a hydrogen-air
mixture.
Localized hot points in the chamber and the temperature of the
residual gas are sometimes sufficient to cause backfiring. 73
73
74
74
37
Compared with hydrocarbon fuels, hydrogen has certain advantages
due to its higher chemical reactivity:
38
The properties of methanol, ethanol and gasoline are compared in
the table.
77
77
Fuel Characteristics:
1- The heat of combustion of the fuel is decreased when the ratio of
C/H increased. So the paraffins have the highest heating value
while the alcohols have the lowest.
6- For the same family, the delay time increases when the molecule is
complex.
78
78
39
The characteristics of the IC engine fuels must be such that the
following requirements are met:
1- The fuel should get effectively atomized, vaporized and well mixed
with the air.
2- The combustion process must be fast.
(a) The type of the equipment required to store, supply and burn the
fuel in the engine.
(c) the availability and cost of the fuel at the site of the engine.
80
80
40
Octane number:
Octane number of a fuel is the percentage by volume of the iso-
octane in a mixture of iso-octane and normal heptane and which will
match the detonation intensity of the fuel when the comparison of
detonation intensity is made in a standardized test engine under
specially agreed operating conditions.
Cetane number:
Cetane number of a fuel is the percentage by volume of normal
cetane in a mixture of normal cetane and alpha methyl naphthalene
which has the same ignition characteristics (ignition delay) as the
test fuel when comparison is carried out in a standard engine under
specific operating conditions.
81
81
USAGE
OF
HYDROCARBONS
82
82
41
It is commonly used as a fuel for engines, barbecues()شوى,
portable stoves( )مواقدand residential central heating )تسخين
(وتدفئة المساكن.
When used as vehicle fuel, it is commonly known as
liquefied petroleum gas (LPG or LP-gas), which can be a
mixture of propane along with small amounts of
propylene, butane, and butylene.
83
83
42
Methane [1C] and ethane [2C] are gaseous at ambient
temperatures and cannot be readily liquefied by pressure
alone.
43
At the opposite extreme from [1C] methane lie the heavy
tars that remain as the lowest fraction in a crude oil
refining retort.
87
87
44
Main Applications of Hydrocarbons:
Liquid fuels:
- Fuels called fossils come from oil. We can define them as a
class of hydrocarbons that come into combustion when
heated in the presence of oxygen.
- The most common today are the different types of gasoline,
diesel and kerosene. They are also used for all industrial
machinery and for electric generators.
- Most of the vehicles work thanks to this type of fuel for what
is, to this day, irreplaceable.
Natural gas:
45
Manufacturing of Plastics:
- Another of the uses that is given to hydrocarbons is the
manufacture of plastics. For this they need a processing that
takes place in the petrochemical industry.
91
91
- The most common compounds are the same oil and mineral
oil. Both are widely used in moisturizers or lotions, since
they give a feeling of softness.
- However, the use of these materials in beauty or cleaning
articles may have little future. Research by various agencies
has warned of possible negative health effects.
- The World Health Organization itself recommends not using
these components as they may be carcinogenic.
92
92
46
Insecticides and pesticides:
- Hydrocarbons are one of the compounds most present in the
different types of insecticides and pesticides.
- Its use goes back to the 40's of last century. It was then that
they began to use the chlorinated ones to try to eradicate the
different plagues that ravaged the harvests.
- Can be cheap.
47
Disadvantages of Burning Hydrocarbons:
- If complete combustion (when fuels burn in plenty of air) occurs, water and carbon
dioxide are released. Carbon dioxide is a greenhouse gas, which restricts radiation of
heat away from earth.
- Oil and coal contain sulfur compounds. When they burn, they release sulfur dioxide.
As well as being a respiratory irritant, sulfur dioxide is dissolved by rain, making acid
rain. This damages limestone buildings it also changes the PH of the soil (key links).
- Aggressive conditions cause the normally unreactive nitrogen to react. This forms
nitrogen oxides, which are irritants and can also contribute to acid rain.
95
95
THE END
96
96
48