Organic Chemistry – Petroleum/Crude Oil

Students should be able to:

(a) state that the naphtha fraction from crude oil is the main source of hydrocarbons
used as the feedstock for the production of a wide range of organic compounds
(b) describe the issues relating to the competing uses of oil as an energy source
and as a chemical feedstock

Introduction to Organic Chemistry

What are organic compounds?

All organic compounds contain carbon. Most organic compounds also contain hydrogen.
Hydrocarbons are compounds that contain carbon and hydrogen only.
Organic compounds may also contain other elements like oxygen (for example, alcohols and
organic acids) and nitrogen (for example, amino acids).

Organic compounds are found in all animals and plants, and even things like plastics and medicines.
However, not all carbon-containing compounds are organic compounds. For example, carbon
dioxide, carbon monoxide and carbonates are not classified as organic compounds.

Formation of Petroleum and Natural Gas

Petroleum and natural gas are mixtures of hydrocarbons, mainly

alkanes. Millions of years ago, dead plants and animals formed layers,
for example, at the bottom of the sea, and were buried under mud and
sand. The dead and decaying plants and animals were subject to great
heat and pressure, and were slowly converted to a dark, sticky liquid,
called petroleum or crude oil. Some of it was changed to a gas called
natural gas.

Petroleum and natural gas are often found together, held in between
layers of non-porous rock, hundreds or thousands of metres below the Figure 1 Extraction of
surface of the earth. These fuels are extracted by drilling deep Petroleum and Natural
wells through the rock. Gas

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Fractional Distillation of Petroleum

 Petroleum is a mixture of different alkanes with different boiling points.

 Petroleum can be separated into useful fractions (or parts) using fractional distillation.
 The separation into fractions is based on the different range of boiling points.
 Each fraction consists of a mixture of hydrocarbons which boils over a certain temperature
range.
 Hydrocarbons more carbon atoms have higher boiling points whereas those with fewer carbon
atoms have lower boiling points.

Process :
1. Petroleum is heated in a furnace and vapourised. The hot vapour will flow up the fractionating
column and start to cool down.
2. Each fraction condenses at a different temperature and comes out of the column at different
height depending on their boiling points.
3. The hydrocarbons with the lower boiling point range will distill over at the top of the column,
where the temperature is lower, while the ones with the higher boiling point range will distil over
at the bottom where the temperature is higher.
4. The process is called selective condensation.

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The Different Fractions and Their Uses

Fraction No. of Boiling Point Uses

carbon Range (ºC)
atoms (n)
Petroleum gas 1–4 < 40 Fuel for cooking
Petrol 5 – 10 40 – 75 Fuel for car engines
(Gasoline)
Naphtha 7 – 14 75 – 150 Feedstock (raw material) for
petrochemicals (E.g. plastics, detergents,
alcohol, drugs)
Kerosene 11 – 16 160 – 250 Fuel for jet engines; cooking and heating
(Paraffin)
Diesel 16 – 20 250 – 300 Fuel for diesel engines of buses, taxis and
lorries
Lubricating oil 20 – 35 300 – 350 Lubricants for machines; making of waxes
and polishes
Bitumen >70 > 350 Make road surfaces

All the fractions are insoluble in water and burn in air.

As n increases per molecule,
 the boiling points increases.(Relative molecular mass and molecular size increases, IMF/VDW
forces strengthen, more energy needed to break the IMF/VDW forces, bp increases)
 the liquids become more viscous (flow less easily).
 the liquids burn less easily, meaning flammability decreases. (more bonds to be broken, Ea
increases)
 when the liquids burn, they burn with a more sooty flame, ie. more carbon produced.
(percentage by mass of carbon increases so more oxygen needed for complete combustion per
unit mass of hydrocarbon)

Issues related to Fossil Fuels

 Petroleum is a finite non-renewable resource and the world’s petroleum reserves are depleting.
 The supply of petroleum is being depleted very rapidly, and there is a need for its conservation.
 Petroleum, besides being used as fuel, has other important uses like being used as a raw material
for the manufacture of essential chemical compounds like medicine and plastics.
 Combustion of petroleum also contributes to pollution (due to the production of CO and C) and
global warming (due to the production of CO2).

 One way of conserving petroleum is to cut down on its use as a fuel.

 We can also save fossil fuels by using alternative energy sources, like solar energy and nuclear
energy.

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Alternative Fuels

One possible source of alternative fuel comes from plants. In Malaysia, palm oil is being used to
run vehicles fitted with special engines. In Brazil, ethanol is being used as a fuel.
Another important fuel is methane, which is the gas produced when organic matter (waste material
from plants and animals) is allowed to decay in the absence of air. Biogas contains about 50%
methane.
Another possible fuel is hydrogen, which can be obtained from water. Hydrogen, when burnt,
produces only steam, which is a non-pollutant. Hydrogen also produces more energy per gram when
burnt, than any other common fuel.

Advantages of using hydrogen as an alternative fuel:

1. Clean fuel, producing only water.
2. Renewable, can be manufactured. (Note that this only applies if hydrogen is obtained from
water instead of petroleum)
3. Produces more energy per unit mass (reaction is more exothermic).

Classification of Organic Compounds

Organic compounds are divided into 2 main categories – hydrocarbons and non-hydrocarbons. They
are then divided further into different homologous series.

Organic Compounds

Hydrocarbons Non-hydrocarbons

Alkanes Alkenes Alkynes Alcohols Carboxylic acids Esters

in sy

Definitions :
1. A homologous series is a family of organic compounds which conform to the general formula
and each member differs from the next by a –CH2 group.
2. Compounds in the same homologous series contain the same functional group and have similar
chemical properties.
3. A functional group is an atom or a group of atoms that gives a molecule its characteristic
properties.

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 Figure 3. Different functional groups

In general, organic compounds in the same homologous series have a few properties in common:

 They have the same functional group, so they have similar chemical properties.
 There is a gradual change in their physical properties.

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Naming Organic Compounds

The name of an organic compound is divided into 2 parts. The first part (prefix) tells us the number
of carbon atoms in the compound.

Prefix meth- eth- prop- but- pent- hex- hept- oct- non- dec-
No. of 1 2 3 4 5 6 7 8 9 10
carbon
atoms

The second part (suffix) tells us the functional group of the compound.
Suffix -ane -ene -ol -oic acid
Homologous series alkane alkene alcohol carboxylic acid

For example,

prop ene
eth ol

H H H H
H

H C C C H C C O H

H H H H
propene ethanol

Figure 4. Naming of organic compounds

Propene is an alkene with three carbon atoms per molecule, while ethanol is an alcohol with two
carbon atoms per molecule.

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