Organic Chemistry The Three Stages of Refining

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Crude oil needs to be processed before it can be used. Three major types of operation are performed
to refine the oil into finished products: separation, conversion and treating.

A crude oil separator on one of the artificial islands on the Kashagan field in Kazakhstan. © ROUSSEL
MARC – TOTAL

Separation
In the first step, molecules are separated through atmospheric distillation (i.e. at normal atmospheric
pressure), according to their molecular weight. During the process, which is also known as topping
(refining), the oil is heated at the bottom of a 60-meter distillation column at a temperature of 350 to
400°C, causing it to vaporize. The vapours rise inside the column while the heaviest molecules, or
residuals, remain at the bottom, without vaporizing. As the vapours rise, the molecules condense
into liquids at different temperatures in the column. Only gases reach the top, where the
temperature has dropped to 150°C. The liquids, which are become increasingly light the higher they
are found in the column, are collected on trays located at different heights of the column. Each tray
collects a different petroleum cut (fraction), also known as a petroleum cut, with highly viscous
hydrocarbons like asphalt  (bitumen) at the bottom and gases at the top.  

The heavy residuals left over after atmospheric distillation still contain many products of medium
density. The residuals are transferred to another column where they undergo a second distillation to
recover middle distillates like heavy fuel oil and diesel. 

Conversion
There are still many too heavy hydrocarbon  molecules remaining after the separation process. To
meet demand for lighter products, the heavy molecules are “cracked” into two or more lighter ones.

The conversion process, which is carried out at 500°C, is also known as catalytic cracking because it
uses a substance called a catalyst to speed up the chemical reaction. This process converts 75% of
the heavy products into gas, gasoline and diesel. The yield can be increased further by adding
hydrogen  a process called hydrocracking, or by using deep conversion to remove carbon.
 The more complex the operation, the more it costs and the more energy it uses. The refining
industry’s ongoing objective is to find a balance between yield and the cost of conversion.

Treating
Treating involves removing or significantly reducing molecules that are corrosive or cause air
pollution, especially sulfur. European Union sulfur emission standards are very stringent. Since
January 1, 2009, gasoline and diesel sold in Europe cannot contain more than 10 ppm (parts per
million)  or 10 milligrams per kilogram, of sulfur. The purpose of these measures is to improve air
quality and optimize the effectiveness of catalytic converters used to treat exhaust gas. For diesel,
desulfurization  or sulfur removal, is performed at 370°C, at a pressure of 60 bar. The hydrogen used
in the process combines with the sulfur to form hydrogen sulfide (H 2S), which is then treated to
remove the sulfur, a substance used in industry.

Kerosene, butane and propane are washed in a caustic soda (sodium hydroxide) solution to remove
thiols, also known as mercaptans. This process called sweetening.

The octane rating measures a fuel’s resistance to detonation, which causes engine knocking.
Treating Automotive Fuels
Automotive fuels must also be treated to increase their octane rating, which is a measure of a fuel’s  
resistance to detonation, based on a scale of 0 to 100. (Engine knocking occurs when the fuel in an
internal combustion engine ignites spontaneously with no input from the spark plug.) If the octane
rating isn’t high enough, the engine will eventually be irreversibly damaged. To avoid this, it is
necessary to boost the octane rating to 95 or 98.

The process used to produce high-octane products is called catalytic reforming. The chemical
reactions during catalytic reforming, which uses platinum as a catalyst, occur at 500°C and a pressure
of 10 bar. They convert some of the naphthenic hydrocarbons (saturated cyclic hydrocarbons) into
aromatic hydrocarbons (unsaturated cyclic hydrocarbons), which have a much higher octane rating.
Other chemical reactions, such as alkylation  also improve the octane rating.

Refined Petroleum Products and Their Uses

Each refined petroleum product obtained from crude oil has a specific use:

a) Liquefied petroleum gas (LPG), also known as butane (C 4H10) and propane (C3H8), is used as an
automotive fuel or packaged in bottles and used for household purposes.

b) Gasoline and diesel are used as fuels for motor vehicles.

c) Kerosene is used as jet fuel.

d) Naphtha is a major petrochemical feedstock.

e) Heating oil is used to heat buildings.

f) Base oils are used to make lubricants.

g) Asphalt, sometimes called bitumen, is used to pave roads.

 
Additional Information Organic Chemistry Key Concepts

 Organic chemistry is the study of organic compounds and the compounds of carbon are
called organic compounds.
 The main sources of carbon containing compounds are coal, petroleum and natural gas
(fossil fuels).
 Because of the highest bonding capacity of carbon, there are more than nine million organic
compounds. Some of them are synthesized and some of them are obtained from natural
sources.
 Hydrocarbons are the simplest organic compounds containing carbon and hydrogen.
Hydrocarbons can be classified as aliphatic compounds and aromatic compounds
 Aliphatic compounds can be classified as saturated and unsaturated hydrocarbons.
Saturated hydrocarbons are alkanes. They have only single bonds.
Unsaturated hydrocarbons are alkenes having double bond(s) and alkynes having triple
bond(s).
 Aromatic compounds (arenes) characterized by having a benzene ring and its derivatives.
 Nomenclature
IUPAC (The International Union of Pure and Applied Chemistry) is the universally recognized
authority on chemical nomenclature and terminology. https://iupac.org/
In 1892, the International Union of Chemistry met in Geneva, Switzerland, and
recommended a systematic set of rules for naming organic compounds. The basic guidelines
for naming organic compounds are still referred to as the Geneva convention.

Activity 1 What word from the text means:

a. Organic compound containing hydrogen and carbon only. hydrocarbon

b. Substance which is burnt to release energy fuel

c. Substance in a gaseous state vapor

d. Containing carbon atoms with no double or triple bonds saturated

hydrocarbon

e. The amount of a desired product that results from a process of manufacture.

yield

f. (For a liquid) does not flow easily viscous

g. Petrol gasoline

h. The process of burning combustion

 i. A substance that accelerates a chemical reaction without being changed by
the reaction catalyst

Activity 2 Answer the following questions:

1.What are the three major types of operation to refine the oil into finished products?

Separation, conversion and treating

2. What happens in the first step, separation?

In the first step, molecules are separated through atmospheric distillation (i.e. at normal
atmospheric pressure), according to their molecular weight.

4. What is the purpose of sweetening process?

to remove thiols.

5. What does the octane rating measure?

The octane rating measure a fuel’s resistance to detonation, which causes engine knocking.

6. What is catalytic reforming?

The process used to produce high-octane products.

7. What is the purpose of alkylation?

To improve the octane rating.

8. What happens when the fuel in an internal combustion engine ignites spontaneously with no input
from the spark plug?

Engine knocking occurs.

9. What happens if the octane rating is not enough? And what can be done to prevent it?

The engine will be irreversibly damaged. To avoid this it is necessary to boost the octane rating to
95 or 98.

10. What does IUPAC stand for?

The International Union of Pure and Applied Chemistry

11. What do we call the organic compounds having benzene ring and its derivatives?

Aromatic compounds (arenes)

12. How do we classify hydrocarbons?

Aliphatic and aromatic

13. What do we call the hydrocarbons having double bonds?

Alkenes
Activity 3 Fill in the following blanks:

a) …Liquefied petroleum gas (LPG)…., also known as butane and propane, is used as an
automotive fuel or packaged in bottles and used for household purposes.

b) …Gasoline… and …diesel… are used as fuels for motor vehicles.

c) Kerosene is used as …jet… fuel.

d) ..Naphtha.. is a major petrochemical feedstock.

e) ..Heating oil… is used to heat buildings.

f) Base oils are used to make …lubricants…. .

g) Asphalt, sometimes called ..bitumen.., is used to pave roads.

h) …Alkynes… are the hydrocarbons having triple bonds.

i) Because of the highest …bonding… capacity of carbon, there are more than nine million
organic compounds.
j) Saturated hydrocarbons have only ….single… bonds.