Presentation No.

1
Crude Oil
Welcome to the New Academic Year
2021-2022
Attestation I Attestation II
Lab works 20 points Lab works 20 points
(Teacher lab ) (Teacher lab )
Midterm exam 10 points End term exam 10 points
(Negim) (Negim)
Total 30 points Total 30 points

Final exam 40 points

(Negim)
 Course Policy Students who are late for the lesson do not have the right to enter the
classroom. Cell phones should be turned off during class and lab work. It
is inadmissible to use telephones as a computer during the training.
Assistance Student can receive answers to all questions on the discipline during the
office hours of the teacher and assistants.

Course structure:
Week Lecture course Lab
I Introduction. Crude Oil. Laboratory Safety Guidelines
Origin - How do oil and gas form?

2 Distilling Crude oil Exp. 1 Fractional Distillation of Crude

Fractional distillation of Crude oil. oil
Methane. ethane. oroDane. butane. oentane Control work # 1. Defense of Exp" 1
a
J Petroleum Chemistrv: Hvdrocarbons of
oetroleum
4 Functional group Exp.2 Determination of (a) Kinematic;
Aromatic hydrocarbon (b) Engler Viscosity of Oil Products
Saturated vs. unsaturated hvdrocarbon
5 Refining process Control work # 2. Defense of Exp.2.
Des alting/dehydration
Crude distillation
6 Propane deasphalting Exp. 3 Specific Gravity Determination
Solvent extraction and dewaxing by (a) pycnometer and (b) by
Aromatic solvent extraction Hydrometer
7 Solvent dewaxing Control work # 3. Defense of Exp.3.
Blendine
6 Midterm exam Collection points of attestation I
9 Thermal process Exp. 4 Standard Test Methods for Flash
Visbreaking and Fire Points by Closed and Open
Delaved cokins Cups Testers
l0 Catalytic processes
Fluid catalytic cracking Control work # 4. Defense of Exp. 4
Hvdrotreatine
i1 Hydrocracking Exp. 5 Demulsification of Water-Oil
Catalytic reforming Emulations
Alkylation
Catalvst deactivation Control work # 5. Defense of Exp. 5
I2 Classifi cation of petroleum.
Sulfur and metal content.
Physical properties. Density. Viscosity.
Temperature points.
l3 Marine Fuel Oil. The basic content of the Exp. 6 Standard Test Method for
main groups of fuel oil. The most important Octane Number of Gasoline.
properties of marine fuel. Properties of Gasoline
t4 Fuel oil standards. Lubricants. Lubricatine
additives. Control work # 6. Defense of Exp.6
l5 End term exam Collection points attestation II
Final exam
The maximum points are as follows:

Attestation I Attestation II
Lab works 20 points Lab works 20 points
Midterm exam l0 points End term exam 10 points
Total 30 points Total 30 points

The syllabus was discussed at the meeting of the Department. Protocol J\b I from 1710812020.

Professor El-Sayed Negim

 Composition of Crude oil
l Crude oil (petroleum) is a naturally occurring
brown to black flammable liquid .
l All crude oils are mainly constituted of
hydrocarbons mixed with variable amounts of
sulfur, nitrogen, and oxygen compounds
l Metals in the forms of inorganic salts or
organometallic compounds are present in the
crude mixture in trace amounts
Fractional Distillation
Fractional Distillation
Crude oil is a mixture of different substances, most of them being hydrocarbons

H H H H
Example of a H C C C C H
hydrocarbon H H H H

Some other
substances
S

Hydrocarbons are molecules which contain the elements hydrogen and carbon only.

Fractional Distillation – it is possible to separate hydrocarbons by fractional distillation

because hydrocarbons boil at different temperature ranges

What is crude oil?

Fractional Distillation in a laboratory
What are hydrocarbons?
What
The reaction is carried outis
in fractional distillation?
a fume cupboard as poisonous gases such as sulphur
dioxide can form.
 Composition of Crude oil
l On average, crude oils are made up of the
following elements or compounds:
– Carbon – 84%
– Hydrogen – 14%
– Sulfur – 1 to 3%
– Nitrogen - <1%
– Oxygen - <1%
– Metals - <1% (nickel, iron,vanadium, etc.)
– Salts - <1%
 Hydrocarbons in Crude Oil
l Paraffins – methane, ethane, propane, butane, etc.
l Aromatics – benzene, naphthalene
l Naphthenes or Cycloalkenes – cyclohexane,
methyl cyclopentane
l Alkenes – ethylene, butene, isobutene
l Dienes and Alkynes – acetylene, butadienes
Distillation in a laboratory

Fractional Distillation in a laboratory

is carried out in a fume cupboard as poisonous gases such as sulphur
orm.
The reaction is carried out in a fume cupboard as poisonous gases
such as sulphur dioxide can form.
As some of the hydrocarbons
Condenser
have similar boiling points a
Fractionating group of them will collect
column
together. Fraction is the name
given to a group of hydrocarbons
Fraction that collect this way.

Heat

e hydrocarbons have similar boiling points a group of them will collect

Øto The
ction is the name given a group hydrocarbon boiling
of hydrocarbons that point
increases
collect this way.
with the size of the carbon chain.
bon boiling point increases with the size of the carbon chain.

al process the crude oil is vaporized. The vapour is let into the column
at the bottom an cools up the column. The fractions with shorter chains
oiling points and can condense higher up the column. The longer
condense at a lower level in the column.
 Distilling Crude Oil
Separate fractions based on differences
in boiling point.

In the industrial process the crude oil is

vaporized. The vapour is let into the column
where it is hot at the bottom an cools up the
column. The fractions with shorter chains
have lower boiling points and can condense
higher up the column. The longer
hydrocarbons have higher boiling points and
can condense at a lower level in the column.
 is separated into fractions
is separated into fractions The process
The processis
is called
called

Number
Number ofof
Fractionating Boiling
Boilingpoint
point Use Use
Fractionating Fraction
Fraction carbon
carbon atomsinin
atoms range
column a chain range
column a chain
Gas 1 4 -160 to 25 Fuel
Gas 1 4 -160 to 25 Fuel

Petrol 4 12 40 to 100 Car fuel

Petrol 4 12 40 to 100 Car fuel
Naphtha 7 14 100 to 150 Chemicals

Naphtha
Kerosene 7 1114 15 100toto250
150 150 JetChemicals
fuel

Diesel oil
Kerosene 11 151519 250
150toto350
250 HeatingJet
fuelfuel

Lubricating oil 20 30 over 350 Car oil

Diesel oil 15 19 250 to 350 Heating fuel

Lubricating oil 20 30 over 350 Car oil

Bitumen C30 above over 400 Road pitch

Heated
Crude oil

Bitumen C30 above over 400 Road pitch

Heated Crude oil is separated into less complex mixtures, these are called fractions. Fractions
Describe the fraction distillation of crude oil?
Crude oil contain hydrocarbons with , e.g. the petrol fraction has
hydrocarbons with boiling points in the range 40-

are at the of the column as they do not boil until a

 very high temperature.

Some of the fractions are used as (e.g. kerosine – aeroplane fuel) others are further
processed by .

Properties of the fractions

As the length of the chain increases:

1. The colour of the fraction turns

from colourless – yellow - brown.
2. They are harder to ignite.
3. They burn dirtier.
4. They get more viscous

Short Long
chain chain

www.bangor.ac.uk What are the

GCSE Science: properties
Chemistry 2 of the fractions? 27
 Composition of Crude oil
Hydrocarbons
Hydrogen Distinguishing Major hydrocarbons Remarks
family characteristics
Paraffins Straight carbon Methane, ethane, General formula CnH2n+2
(Alkanes) chain propane, butane, Boiling point increases as the
pentane, hexane number of carbon atom
increases. With number of
carbon 25-40, paraffin becomes
waxy.
Iso paraffins Branched carbon Isobutane, isopentane, The number of possible isomers
(Iso alkanes) chain neopentane, isooctane increases as in geometric
progression as the number of
carbon atoms increases.
 Composition of Crude Oils
Alkanes (Paraffines)
l Alkanes are saturated hydrocarbons having the
general formula CnH2n+2
l The alkanes (paraffins), are saturated
hydrocarbons with straight (normal) or branched
(iso) chains which contain only carbon and
hydrogen
l Crude oils contain many short, medium, and long-
chain normal and branched paraffins
l
 Methane H
H
109.5o
CH4 H C H C
H H

H H

molecular structural molecular

formula formula shape

C
H
H
H
tetrahedral tetrahedron ball-and-stick
shape of model
methane
Methane is Tetrahedral

C H
H

H
Methane is Tetrahedral
Lewis structure of Ethane

H H

H C C H

H H
Structure of Propane
Structure of Butane
 First Ten Hydrocarbons
Number of Molecular Condensed Structural
Name Carbon Atoms Formula Formula

Methane 1 CH4 CH4

Ethane 2 C2 H6 CH3CH3

Propane 3 C3 H8 CH3CH2CH3

Butane 4 C4H10 CH3CH2CH2CH3

Pentane 5 C5H12 CH3CH2CH2CH2CH3

Hexane 6 C6H14 CH3CH2CH2CH2CH2CH3

Heptane 7 C7H16 CH3CH2CH2CH2CH2CH2CH3

Octane 8 C8H18 CH3CH2CH2CH2CH2CH2CH2CH3

Nonane 9 C9H20 CH3CH2CH2CH2CH2CH2CH2CH2CH3

Decane 10 C10H22 CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3

l The alkanes from pentane (C5H12) to octane
(C8H18) are refined into petrol.
l from nonane (C9H20) to hexadecane (C16H34) into
diesel fuel, kerosene and jet fuel.
l More than 16 carbon atoms can be refined into
fuel oil and lubricating oil.
l Paraffin wax is an alkane with approximately 25
carbon atoms, while asphalt has 35 and up
l the shortest molecules, those with four or fewer
carbon atoms, are in a gaseous state at room
temperature.
 First Ten Hydrocarbons
Number of Molecular Melting Boiling # of
Name Carbon Atoms Formula Point, oC Point, oC Isomers

Methane 1 CH4 -182.5 -161.5 0

Ethane 2 C2 H6 -183.2 -88.6 0

n-Propane 3 C3 H8 -187.7 -42.1 0

n-Butane 4 C4H10 -138.3 -0.5 2

n-Pentane 5 C5H12 -129.7 36.1 3

n-Hexane 6 C6H14 -95.3 68.7 5

n-Heptane 7 C7H16 -90.6 98.4 9

n-Octane 8 C8H18 -56.8 125.7 18

n-Nonane 9 C9H20 -53.6 150.8 35

n-Decane 10 C10H22 -29.7 174.0 75

Increasing mass and boiling point

Methane Ethane Propane n-Butane

16 g/mol 30 g/mol 44 g/mol 58 g/mol
-161.5oC -88.6oC -42.1oC -0.5oC
 H H H H H
H C H H C C C C H
H H H H H
Methane Butane
CH4 C4H10

H H H H H
R
?
C H
R C C C C H
H
H H H H
Methyl
-CH3 Butyl
-C4H9
 Butane
Butane: C4H10

H H H H
H-C-C-C-C-H
H H H H

Butane Gas
– lighters
Structural Isomers of C4H10
 butane
H H H H
H C C C C H
H H H H

C4H10
Isomers of
Butane
H HH
H C H
H C C C H
methyl propane or isobutane H H H
Isomers of Pentane
C5H12

These are called structural isomers.

 Naming Alkanes
1. Find the longest continuous chain of carbon atoms in the molecule
2. Start numbering the chain at the carbon nearer the first branching point
(the substituents should have the lowest numbers possible)
3. Name and number the substituents
If there are two substituents attached to the same carbon,
assign both of them the same number
4. Write out the name of the molecule
•List the substitutents names in alphabetical order
if there are two identical substituents on the molecule, use the prefix di;
if there are three identical substituents, use the prefix tri-;
if there are four identical substituents, use the prefix tetra-
(alphabetize the substituents by the main name of the substituent,
not by any prefixes the substituents may have)
•Separate the substituents names with hyphens
•Tag the name of the parent chain onto the end of the substituent names
 H

H H
H C H H H

H C C C C C H

H H H H
H C H
C7H16
2, 4-dimethyl pentane
H molecular formula

H H H H H H H
condensed H C C C C C C C H
structural
formula H H H H H H H
Heptane

shorthand
 H H H H
H C C C C H
H H H

H C H
H

butane
2 - methylbutane
 Naming Branched Alkanes (IUPAC)
Octane 4-ethyl
6 2
8
5 4-ethyl-3,5-dimethyloctane
4
7 3 1
3-methyl and 5-methyl = 3,5-dimethyl
1. Root name: name of longest continuous C chain (parent chain)
Two equally long? Choose the one with more branches
2. Number C atoms in chain, starting at end with first branch
3. Identify substituents, give each a number (C it is connected to)
Two or more identical substituents: use prefixes (di-, tri-, tetra-, etc.)
4. List substituents alphabetically before root name
Do not alphabetize prefixes
5. Punctuation: commas separate numbers from each other
hyphens separate numbers from names
no space between last substituent & root name
 H H CH3
H C C C
1
6 52 43 CH3
H H C H 3
4
CH3

H C H 25
C C C C C C

H C H CH3
16

H
3, 3 dimethyl hexane
or Lowest sum of numbers
is correct
4, 4 dimethyl hexane
Structural Isomers: Pentane (C5H12)

pentane

2-methylbutane

2,2-dimethylpropane
Structural Isomers: Hexane (C6H14)

hexane

2,3-dimethylbutane
2-methylpentane

2,2-dimethylbutane
3-methylpentane
Structural Isomers: Heptane (C7H16)

heptane

2,2-dimethylpentane

2-methylhexane

2,3-dimethylpentane
3-methylhexane
Structural Isomers: Heptane C7H16

2,4-dimethylpentane 3-ethylpentane

3,3-dimethylpentane 2,2,3-trimethylbutane
 Comparing Structural Isomers
(Same formula, different structure)
C5H12
Structure Name Boiling point (°C)

pentane 36.0

2-methylbutane 27.9

2,2-dimethylpropane 9.5

BP/MP of Linear alkanes > BP/MP of branched alkanes

 Naming Alkanes Problem Set
1. 2.

2-methylbutane 2-methylbutane

3. 4.

2,3-dimethylbutane 3,3,4-trimethylhexane
 Naming Alkanes Problem Set
5. 3-ethyl-2,4,5-trimethylheptane

6. 6-ethyl-2,7-dimethylnonane
 Naming Alkanes Problem Set
7. 8.

2,3,4-trimethylhexane 4-ethyl-3-methylheptane

9. 10.

5-tert-butyl-4-isopropyl-3-
3,3,4-trimethylhexane
methyloctane
 Naming Alkanes Problem Set
11. 2,2,3-trimethylheptane

12. 6-ethyl-2-methyl-5-propylnonane
 Naming Alkanes Problem Set

13. 14.

3,5-dimethyl-4-propylheptane 3,4,4-trimethylheptane

15. 16.

3-ethyl-2,2,3- 4-ethyl-6-isobutyl-2,9-
trimethylpentane dimethyldecane
 Naming Alkanes Problem Set
17.

4
2
6
8 2-methyloctane
1 3 5 7

18.
1
7
6
2
3 5
4

4-isopropyl-2,2,3,5-tetramethylheptane
 Naming Alkanes Problem Set
19.

4 6 10
2 5 8
1 3 7 9

2,5,8-trimethyldecane
20.

4 6
2 3
1 5 7

2,2,3-trimethylhexane
 H

3,4-dimethyl octane H C H
H C H

H H H H H H
H C C C C C C C H
H H H H H H

H C H
H
 Mirror images

Optical Isomers of
3-methylhexane